# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_(2a)

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 F10 N2, C2 H6 O S, Br, Cl'
_chemical_formula_sum            'C22 H26 Br Cl F10 N2 O S'
_chemical_formula_weight         671.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9241(2)
_cell_length_b                   12.7624(3)
_cell_length_c                   16.7270(4)
_cell_angle_alpha                111.6180(10)
_cell_angle_beta                 90.966(2)
_cell_angle_gamma                93.449(2)
_cell_volume                     1370.46(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5586
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             676
_exptl_absorpt_coefficient_mu    1.761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5113
_exptl_absorpt_correction_T_max  0.6478
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8300
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         25.25
_reflns_number_total             4939
_reflns_number_gt                4260
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, et al., 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0349P)²+1.6329P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4939
_refine_ls_number_parameters     343
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0897
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.87449(5) 0.58342(3) 0.70119(2) 0.02777(11) Uani 0.60 1 d P . .
Cl1 Cl 0.87449(5) 0.58342(3) 0.70119(2) 0.02777(11) Uani 0.40 1 d P . .
Br2 Br 0.26971(5) 0.11422(3) 0.53359(3) 0.02510(11) Uani 0.40 1 d P . .
Cl2 Cl 0.26971(5) 0.11422(3) 0.53359(3) 0.02510(11) Uani 0.60 1 d P . .
F3 F 0.4014(3) 0.16516(18) 0.81492(13) 0.0520(5) Uani 1 1 d . . .
F4 F 0.4477(4) 0.1018(2) 0.95004(14) 0.0786(8) Uani 1 1 d . . .
F5 F 0.7755(4) 0.0063(2) 0.97097(14) 0.0794(8) Uani 1 1 d . . .
F6 F 1.0637(4) -0.01770(18) 0.85893(15) 0.0687(7) Uani 1 1 d . . .
F7 F 1.0255(3) 0.05451(15) 0.72847(11) 0.0449(4) Uani 1 1 d . . .
F14 F 0.5024(3) 0.13182(14) 0.28106(11) 0.0476(5) Uani 1 1 d . . .
F15 F 0.5014(3) 0.19513(17) 0.14414(12) 0.0598(6) Uani 1 1 d . . .
F16 F 0.5995(3) 0.41405(17) 0.16589(12) 0.0527(5) Uani 1 1 d . . .
F17 F 0.6905(2) 0.56876(14) 0.32583(12) 0.0402(4) Uani 1 1 d . . .
F18 F 0.6940(2) 0.50600(12) 0.46214(10) 0.0326(4) Uani 1 1 d . . .
N1 N 0.7540(3) 0.26358(18) 0.70343(13) 0.0250(5) Uani 1 1 d . . .
N2 N 0.8015(3) 0.24226(18) 0.47033(14) 0.0256(5) Uani 1 1 d . . .
C1 C 0.6866(4) 0.1422(2) 0.68921(17) 0.0284(6) Uani 1 1 d . . .
H1A H 0.5478 0.1293 0.6707 0.034 Uiso 1 1 calc R . .
H1B H 0.7593 0.0908 0.6419 0.034 Uiso 1 1 calc R . .
C2 C 0.7124(4) 0.1123(2) 0.76719(17) 0.0306(6) Uani 1 1 d U . .
C3 C 0.5681(5) 0.1221(3) 0.82555(19) 0.0386(7) Uani 1 1 d U . .
C4 C 0.5899(5) 0.0880(3) 0.8944(2) 0.0511(9) Uani 1 1 d U . .
C5 C 0.7555(6) 0.0400(3) 0.9052(2) 0.0511(9) Uani 1 1 d U . .
C6 C 0.9005(5) 0.0281(3) 0.8484(2) 0.0462(8) Uani 1 1 d U . .
C7 C 0.8781(5) 0.0653(2) 0.78168(19) 0.0366(7) Uani 1 1 d U . .
C8 C 0.9676(4) 0.2880(2) 0.72584(18) 0.0314(6) Uani 1 1 d . . .
H8A H 1.0399 0.2354 0.6802 0.047 Uiso 1 1 calc R . .
H8B H 0.9961 0.2789 0.7804 0.047 Uiso 1 1 calc R . .
H8C H 1.0058 0.3657 0.7315 0.047 Uiso 1 1 calc R . .
C9 C 0.6499(4) 0.3460(2) 0.77536(17) 0.0323(6) Uani 1 1 d . . .
H9A H 0.6786 0.3347 0.8291 0.048 Uiso 1 1 calc R . .
H9B H 0.5101 0.3336 0.7621 0.048 Uiso 1 1 calc R . .
H9C H 0.6932 0.4233 0.7818 0.048 Uiso 1 1 calc R . .
C10 C 0.7016(4) 0.2851(2) 0.62266(16) 0.0269(6) Uani 1 1 d . . .
H10A H 0.7551 0.3615 0.6288 0.032 Uiso 1 1 calc R . .
H10B H 0.5590 0.2829 0.6159 0.032 Uiso 1 1 calc R . .
C11 C 0.7793(4) 0.1983(2) 0.54271(16) 0.0267(6) Uani 1 1 d . . .
H11A H 0.9067 0.1774 0.5575 0.032 Uiso 1 1 calc R . .
H11B H 0.6900 0.1293 0.5228 0.032 Uiso 1 1 calc R . .
C12 C 0.6088(4) 0.2816(2) 0.45228(17) 0.0277(6) Uani 1 1 d . . .
H12A H 0.5070 0.2200 0.4430 0.033 Uiso 1 1 calc R . .
H12B H 0.5763 0.3467 0.5035 0.033 Uiso 1 1 calc R . .
C13 C 0.6067(4) 0.3158(2) 0.37566(17) 0.0266(6) Uani 1 1 d . . .
C14 C 0.5554(4) 0.2398(2) 0.29310(19) 0.0346(6) Uani 1 1 d . . .
C15 C 0.5536(5) 0.2710(3) 0.22271(18) 0.0394(7) Uani 1 1 d . . .
C16 C 0.6021(4) 0.3818(3) 0.23400(18) 0.0361(7) Uani 1 1 d . . .
C17 C 0.6473(4) 0.4598(2) 0.31451(19) 0.0308(6) Uani 1 1 d . . .
C18 C 0.6493(4) 0.4271(2) 0.38365(17) 0.0266(6) Uani 1 1 d . . .
C19 C 0.9611(4) 0.3345(2) 0.49218(17) 0.0291(6) Uani 1 1 d . . .
H19A H 0.9264 0.3996 0.5419 0.044 Uiso 1 1 calc R . .
H19B H 0.9799 0.3574 0.4428 0.044 Uiso 1 1 calc R . .
H19C H 1.0813 0.3069 0.5061 0.044 Uiso 1 1 calc R . .
C20 C 0.8603(4) 0.1446(2) 0.39455(17) 0.0312(6) Uani 1 1 d . . .
H20A H 0.7582 0.0830 0.3790 0.047 Uiso 1 1 calc R . .
H20B H 0.9810 0.1183 0.4093 0.047 Uiso 1 1 calc R . .
H20C H 0.8800 0.1685 0.3458 0.047 Uiso 1 1 calc R . .
S1 S 0.99226(17) 0.37186(8) 0.02766(6) 0.0605(3) Uani 1 1 d . . .
O1 O 0.9019(4) 0.3224(2) -0.06082(16) 0.0642(7) Uani 1 1 d . . .
C21 C 1.0007(9) 0.2590(4) 0.0661(3) 0.0864(16) Uani 1 1 d . . .
H21A H 0.8694 0.2368 0.0777 0.130 Uiso 1 1 calc R . .
H21B H 1.0820 0.2839 0.1192 0.130 Uiso 1 1 calc R . .
H21C H 1.0552 0.1943 0.0224 0.130 Uiso 1 1 calc R . .
C22 C 1.2455(7) 0.3901(4) 0.0136(4) 0.0912(17) Uani 1 1 d . . .
H22A H 1.2695 0.4511 -0.0081 0.137 Uiso 1 1 calc R . .
H22B H 1.2896 0.3197 -0.0278 0.137 Uiso 1 1 calc R . .
H22C H 1.3163 0.4094 0.0689 0.137 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02239(18) 0.02928(19) 0.02901(18) 0.00796(14) 0.00071(13) 0.00024(13)
Cl1 0.02239(18) 0.02928(19) 0.02901(18) 0.00796(14) 0.00071(13) 0.00024(13)
Br2 0.01692(19) 0.0228(2) 0.0372(2) 0.01317(17) 0.00021(15) 0.00071(14)
Cl2 0.01692(19) 0.0228(2) 0.0372(2) 0.01317(17) 0.00021(15) 0.00071(14)
F3 0.0374(10) 0.0697(13) 0.0544(12) 0.0304(10) 0.0086(9) -0.0039(9)
F4 0.0783(16) 0.113(2) 0.0509(13) 0.0438(13) 0.0108(11) -0.0334(14)
F5 0.111(2) 0.0892(17) 0.0553(13) 0.0569(13) -0.0340(13) -0.0438(15)
F6 0.0830(16) 0.0587(13) 0.0767(15) 0.0409(12) -0.0307(12) 0.0044(12)
F7 0.0491(11) 0.0427(10) 0.0432(10) 0.0142(8) 0.0025(8) 0.0173(8)
F14 0.0644(12) 0.0310(9) 0.0422(10) 0.0112(8) -0.0191(9) -0.0142(8)
F15 0.0864(16) 0.0554(12) 0.0298(9) 0.0091(9) -0.0187(10) -0.0039(11)
F16 0.0640(13) 0.0671(13) 0.0410(10) 0.0354(10) 0.0012(9) 0.0114(10)
F17 0.0383(9) 0.0355(9) 0.0571(11) 0.0289(8) 0.0029(8) 0.0034(7)
F18 0.0346(9) 0.0247(8) 0.0353(8) 0.0079(7) -0.0022(7) -0.0005(7)
N1 0.0262(11) 0.0254(11) 0.0245(11) 0.0108(9) -0.0012(9) 0.0003(9)
N2 0.0268(11) 0.0247(11) 0.0256(11) 0.0097(9) 0.0004(9) 0.0006(9)
C1 0.0326(15) 0.0248(13) 0.0280(13) 0.0110(11) -0.0020(11) -0.0025(11)
C2 0.0383(16) 0.0247(13) 0.0280(13) 0.0103(11) -0.0051(12) -0.0063(11)
C3 0.0403(17) 0.0394(16) 0.0350(15) 0.0146(13) -0.0024(13) -0.0097(13)
C4 0.062(2) 0.056(2) 0.0351(16) 0.0223(15) 0.0002(15) -0.0263(17)
C5 0.071(2) 0.0494(19) 0.0405(17) 0.0310(15) -0.0198(17) -0.0237(17)
C6 0.060(2) 0.0358(16) 0.0465(18) 0.0218(14) -0.0198(16) -0.0069(15)
C7 0.0494(18) 0.0273(14) 0.0325(15) 0.0113(12) -0.0054(13) -0.0010(13)
C8 0.0272(14) 0.0352(15) 0.0329(14) 0.0148(12) -0.0043(11) -0.0025(12)
C9 0.0405(16) 0.0315(15) 0.0258(13) 0.0109(12) 0.0031(12) 0.0068(12)
C10 0.0288(14) 0.0286(14) 0.0262(13) 0.0133(11) 0.0000(11) 0.0033(11)
C11 0.0310(14) 0.0263(13) 0.0252(13) 0.0124(11) 0.0000(11) 0.0006(11)
C12 0.0250(14) 0.0295(14) 0.0300(14) 0.0130(11) -0.0015(11) -0.0004(11)
C13 0.0227(13) 0.0293(14) 0.0285(13) 0.0123(11) -0.0023(10) -0.0007(11)
C14 0.0375(16) 0.0287(15) 0.0370(16) 0.0130(12) -0.0087(12) -0.0040(12)
C15 0.0430(18) 0.0448(18) 0.0272(14) 0.0103(13) -0.0101(13) 0.0015(14)
C16 0.0355(16) 0.0487(18) 0.0326(15) 0.0248(14) -0.0006(12) 0.0054(13)
C17 0.0237(14) 0.0313(15) 0.0444(16) 0.0222(13) 0.0002(12) 0.0019(11)
C18 0.0209(13) 0.0297(14) 0.0291(13) 0.0110(11) -0.0018(10) 0.0009(11)
C19 0.0276(14) 0.0298(14) 0.0300(14) 0.0121(12) -0.0018(11) -0.0040(11)
C20 0.0368(15) 0.0277(14) 0.0263(13) 0.0064(11) 0.0014(11) 0.0048(12)
S1 0.0837(7) 0.0418(5) 0.0488(5) 0.0083(4) -0.0216(5) 0.0125(5)
O1 0.0798(19) 0.0621(16) 0.0536(15) 0.0295(13) -0.0309(13) -0.0156(14)
C21 0.155(5) 0.060(3) 0.043(2) 0.017(2) -0.025(3) 0.019(3)
C22 0.079(3) 0.063(3) 0.111(4) 0.009(3) -0.044(3) 0.010(2)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F3 C3 1.345(4) . ?
F4 C4 1.340(4) . ?
F5 C5 1.328(4) . ?
F6 C6 1.341(4) . ?
F7 C7 1.346(4) . ?
F14 C14 1.344(3) . ?
F15 C15 1.341(3) . ?
F16 C16 1.347(3) . ?
F17 C17 1.346(3) . ?
F18 C18 1.345(3) . ?
N1 C9 1.504(3) . ?
N1 C8 1.505(3) . ?
N1 C10 1.517(3) . ?
N1 C1 1.521(3) . ?
N2 C20 1.497(3) . ?
N2 C19 1.502(3) . ?
N2 C11 1.517(3) . ?
N2 C12 1.518(3) . ?
C1 C2 1.499(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C7 1.384(4) . ?
C2 C3 1.387(4) . ?
C3 C4 1.383(4) . ?
C4 C5 1.371(5) . ?
C5 C6 1.370(5) . ?
C6 C7 1.375(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.520(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.498(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.389(4) . ?
C13 C18 1.390(4) . ?
C14 C15 1.375(4) . ?
C15 C16 1.375(4) . ?
C16 C17 1.365(4) . ?
C17 C18 1.367(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
S1 O1 1.488(2) . ?
S1 C21 1.783(4) . ?
S1 C22 1.786(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C8 107.4(2) . . ?
C9 N1 C10 106.52(19) . . ?
C8 N1 C10 111.1(2) . . ?
C9 N1 C1 111.3(2) . . ?
C8 N1 C1 112.2(2) . . ?
C10 N1 C1 108.19(19) . . ?
C20 N2 C19 107.8(2) . . ?
C20 N2 C11 105.7(2) . . ?
C19 N2 C11 110.9(2) . . ?
C20 N2 C12 111.4(2) . . ?
C19 N2 C12 112.0(2) . . ?
C11 N2 C12 108.8(2) . . ?
C2 C1 N1 114.0(2) . . ?
C2 C1 H1A 108.8 . . ?
N1 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
N1 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C7 C2 C3 116.0(3) . . ?
C7 C2 C1 121.4(3) . . ?
C3 C2 C1 122.5(3) . . ?
F3 C3 C4 118.7(3) . . ?
F3 C3 C2 119.5(3) . . ?
C4 C3 C2 121.8(3) . . ?
F4 C4 C5 120.5(3) . . ?
F4 C4 C3 119.4(4) . . ?
C5 C4 C3 120.0(3) . . ?
F5 C5 C6 120.3(4) . . ?
F5 C5 C4 120.0(4) . . ?
C6 C5 C4 119.7(3) . . ?
F6 C6 C5 120.2(3) . . ?
F6 C6 C7 120.5(3) . . ?
C5 C6 C7 119.3(3) . . ?
F7 C7 C6 117.5(3) . . ?
F7 C7 C2 119.4(3) . . ?
C6 C7 C2 123.1(3) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C11 112.0(2) . . ?
N1 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
N1 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N2 C11 C10 112.2(2) . . ?
N2 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
N2 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 N2 113.8(2) . . ?
C13 C12 H12A 108.8 . . ?
N2 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
N2 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C18 115.8(2) . . ?
C14 C13 C12 122.5(2) . . ?
C18 C13 C12 121.6(2) . . ?
F14 C14 C15 118.2(3) . . ?
F14 C14 C13 119.2(3) . . ?
C15 C14 C13 122.6(3) . . ?
F15 C15 C14 120.6(3) . . ?
F15 C15 C16 120.2(3) . . ?
C14 C15 C16 119.2(3) . . ?
F16 C16 C17 119.9(3) . . ?
F16 C16 C15 120.0(3) . . ?
C17 C16 C15 120.1(3) . . ?
F17 C17 C16 120.1(3) . . ?
F17 C17 C18 120.0(3) . . ?
C16 C17 C18 119.9(3) . . ?
F18 C18 C17 118.5(2) . . ?
F18 C18 C13 119.1(2) . . ?
C17 C18 C13 122.4(2) . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 S1 C21 106.58(18) . . ?
O1 S1 C22 105.4(2) . . ?
C21 S1 C22 97.8(3) . . ?
S1 C21 H21A 109.5 . . ?
S1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C2 -57.9(3) . . . . ?
C8 N1 C1 C2 62.5(3) . . . . ?
C10 N1 C1 C2 -174.6(2) . . . . ?
N1 C1 C2 C7 -92.6(3) . . . . ?
N1 C1 C2 C3 92.1(3) . . . . ?
C7 C2 C3 F3 -178.9(2) . . . . ?
C1 C2 C3 F3 -3.3(4) . . . . ?
C7 C2 C3 C4 0.6(4) . . . . ?
C1 C2 C3 C4 176.1(3) . . . . ?
F3 C3 C4 F4 -2.1(5) . . . . ?
C2 C3 C4 F4 178.5(3) . . . . ?
F3 C3 C4 C5 177.6(3) . . . . ?
C2 C3 C4 C5 -1.8(5) . . . . ?
F4 C4 C5 F5 0.3(5) . . . . ?
C3 C4 C5 F5 -179.4(3) . . . . ?
F4 C4 C5 C6 -179.0(3) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
F5 C5 C6 F6 0.0(5) . . . . ?
C4 C5 C6 F6 179.4(3) . . . . ?
F5 C5 C6 C7 -178.9(3) . . . . ?
C4 C5 C6 C7 0.4(5) . . . . ?
F6 C6 C7 F7 -0.4(4) . . . . ?
C5 C6 C7 F7 178.5(3) . . . . ?
F6 C6 C7 C2 179.4(3) . . . . ?
C5 C6 C7 C2 -1.7(5) . . . . ?
C3 C2 C7 F7 -179.0(2) . . . . ?
C1 C2 C7 F7 5.4(4) . . . . ?
C3 C2 C7 C6 1.2(4) . . . . ?
C1 C2 C7 C6 -174.5(3) . . . . ?
C9 N1 C10 C11 -173.5(2) . . . . ?
C8 N1 C10 C11 69.8(3) . . . . ?
C1 N1 C10 C11 -53.8(3) . . . . ?
C20 N2 C11 C10 -174.8(2) . . . . ?
C19 N2 C11 C10 68.7(3) . . . . ?
C12 N2 C11 C10 -55.0(3) . . . . ?
N1 C10 C11 N2 -156.8(2) . . . . ?
C20 N2 C12 C13 -57.8(3) . . . . ?
C19 N2 C12 C13 63.1(3) . . . . ?
C11 N2 C12 C13 -173.9(2) . . . . ?
N2 C12 C13 C14 89.8(3) . . . . ?
N2 C12 C13 C18 -92.6(3) . . . . ?
C18 C13 C14 F14 -176.5(2) . . . . ?
C12 C13 C14 F14 1.1(4) . . . . ?
C18 C13 C14 C15 2.4(4) . . . . ?
C12 C13 C14 C15 -179.9(3) . . . . ?
F14 C14 C15 F15 -0.4(5) . . . . ?
C13 C14 C15 F15 -179.4(3) . . . . ?
F14 C14 C15 C16 178.2(3) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
F15 C15 C16 F16 -0.8(5) . . . . ?
C14 C15 C16 F16 -179.4(3) . . . . ?
F15 C15 C16 C17 177.2(3) . . . . ?
C14 C15 C16 C17 -1.4(5) . . . . ?
F16 C16 C17 F17 -0.4(4) . . . . ?
C15 C16 C17 F17 -178.5(3) . . . . ?
F16 C16 C17 C18 179.8(3) . . . . ?
C15 C16 C17 C18 1.8(4) . . . . ?
F17 C17 C18 F18 0.4(4) . . . . ?
C16 C17 C18 F18 -179.9(2) . . . . ?
F17 C17 C18 C13 -179.7(2) . . . . ?
C16 C17 C18 C13 0.0(4) . . . . ?
C14 C13 C18 F18 177.9(2) . . . . ?
C12 C13 C18 F18 0.2(4) . . . . ?
C14 C13 C18 C17 -2.0(4) . . . . ?
C12 C13 C18 C17 -179.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 967089'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_(2a-2)

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 F10 N2, C2 H6 O S, 2(Br)'
_chemical_formula_sum            'C22 H26 Br2 F10 N2 O S'
_chemical_formula_weight         716.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1359(2)
_cell_length_b                   12.6440(3)
_cell_length_c                   16.7753(4)
_cell_angle_alpha                111.3640(10)
_cell_angle_beta                 91.7140(10)
_cell_angle_gamma                92.9300(10)
_cell_volume                     1405.81(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5727
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    3.043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5813
_exptl_absorpt_correction_T_max  0.6931
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8524
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.86
_diffrn_reflns_theta_max         25.25
_reflns_number_total             5077
_reflns_number_gt                4302
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, et al., 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0606P)²+9.7628P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5077
_refine_ls_number_parameters     343
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1551
_refine_ls_wR_factor_gt          0.1467
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.37279(7) 0.60169(5) 0.70676(3) 0.02795(18) Uani 1 1 d . . .
Br2 Br 0.22809(8) 0.88307(5) 0.46415(4) 0.03256(19) Uani 1 1 d . . .
F5 F 0.8070(5) 0.4895(3) 0.5394(2) 0.0359(8) Uani 1 1 d . . .
F6 F 0.8078(5) 0.4273(3) 0.6760(3) 0.0441(9) Uani 1 1 d . . .
F7 F 0.8933(7) 0.5839(4) 0.8357(3) 0.0609(12) Uani 1 1 d . . .
F8 F 0.9819(8) 0.8052(4) 0.8567(3) 0.0726(15) Uani 1 1 d . . .
F9 F 0.9815(7) 0.8679(3) 0.7196(3) 0.0552(11) Uani 1 1 d . . .
F12 F 0.4772(6) 0.9474(3) 0.2708(2) 0.0453(9) Uani 1 1 d . . .
F13 F 0.4424(7) 1.0239(4) 0.1419(3) 0.0631(13) Uani 1 1 d . . .
F14 F 0.7246(8) 1.0042(5) 0.0338(3) 0.0748(16) Uani 1 1 d . . .
F15 F 1.0444(7) 0.9093(5) 0.0571(3) 0.0761(15) Uani 1 1 d . . .
F16 F 1.0868(6) 0.8412(4) 0.1906(3) 0.0530(11) Uani 1 1 d . . .
N1 N 0.6976(6) 0.7554(4) 0.5286(3) 0.0268(10) Uani 1 1 d . . .
N2 N 0.7440(7) 0.7362(4) 0.2972(3) 0.0284(10) Uani 1 1 d . . .
C1 C 0.7198(8) 0.8011(5) 0.4571(4) 0.0285(12) Uani 1 1 d . . .
H1A H 0.8067 0.8703 0.4777 0.034 Uiso 1 1 calc R . .
H1B H 0.5964 0.8231 0.4420 0.034 Uiso 1 1 calc R . .
C2 C 0.7957(8) 0.7135(5) 0.3770(4) 0.0307(13) Uani 1 1 d . . .
H2A H 0.9342 0.7156 0.3842 0.037 Uiso 1 1 calc R . .
H2B H 0.7444 0.6364 0.3705 0.037 Uiso 1 1 calc R . .
C3 C 0.8860(8) 0.7166(5) 0.5493(4) 0.0300(12) Uani 1 1 d . . .
H3A H 0.9200 0.6511 0.4990 0.036 Uiso 1 1 calc R . .
H3B H 0.9838 0.7791 0.5594 0.036 Uiso 1 1 calc R . .
C4 C 0.8851(8) 0.6827(5) 0.6260(4) 0.0300(12) Uani 1 1 d . . .
C5 C 0.8470(8) 0.5697(5) 0.6173(4) 0.0311(13) Uani 1 1 d . . .
C6 C 0.8480(8) 0.5367(5) 0.6869(4) 0.0347(14) Uani 1 1 d . . .
C7 C 0.8909(10) 0.6160(6) 0.7671(4) 0.0436(16) Uani 1 1 d . . .
C8 C 0.9342(11) 0.7274(6) 0.7783(4) 0.0469(17) Uani 1 1 d . . .
C9 C 0.9319(10) 0.7593(5) 0.7080(4) 0.0404(15) Uani 1 1 d . . .
C10 C 0.8073(9) 0.8595(5) 0.3123(4) 0.0311(13) Uani 1 1 d . . .
H10A H 0.7349 0.9104 0.3587 0.037 Uiso 1 1 calc R . .
H10B H 0.9415 0.8729 0.3322 0.037 Uiso 1 1 calc R . .
C11 C 0.7833(9) 0.8909(5) 0.2347(4) 0.0314(13) Uani 1 1 d . . .
C12 C 0.6213(9) 0.9385(5) 0.2195(4) 0.0360(14) Uani 1 1 d . . .
C13 C 0.6011(11) 0.9779(6) 0.1531(5) 0.0443(17) Uani 1 1 d . . .
C14 C 0.7437(12) 0.9685(7) 0.0992(5) 0.052(2) Uani 1 1 d . . .
C15 C 0.9048(11) 0.9201(7) 0.1111(5) 0.0492(18) Uani 1 1 d . . .
C16 C 0.9242(9) 0.8836(6) 0.1786(4) 0.0400(15) Uani 1 1 d . . .
C17 C 0.5452(8) 0.6608(5) 0.5053(4) 0.0302(12) Uani 1 1 d . . .
H17A H 0.5817 0.5959 0.4562 0.045 Uiso 1 1 calc R . .
H17B H 0.4279 0.6877 0.4901 0.045 Uiso 1 1 calc R . .
H17C H 0.5268 0.6373 0.5542 0.045 Uiso 1 1 calc R . .
C18 C 0.6385(9) 0.8532(5) 0.6039(4) 0.0338(13) Uani 1 1 d . . .
H18A H 0.7363 0.9157 0.6200 0.051 Uiso 1 1 calc R . .
H18B H 0.6200 0.8286 0.6523 0.051 Uiso 1 1 calc R . .
H18C H 0.5207 0.8793 0.5885 0.051 Uiso 1 1 calc R . .
C19 C 0.8468(9) 0.6553(5) 0.2257(4) 0.0346(13) Uani 1 1 d . . .
H19A H 0.8046 0.5768 0.2172 0.052 Uiso 1 1 calc R . .
H19B H 0.9822 0.6671 0.2404 0.052 Uiso 1 1 calc R . .
H19C H 0.8207 0.6692 0.1728 0.052 Uiso 1 1 calc R . .
C20 C 0.5365(8) 0.7116(5) 0.2742(4) 0.0344(13) Uani 1 1 d . . .
H20A H 0.4661 0.7631 0.3201 0.052 Uiso 1 1 calc R . .
H20B H 0.5008 0.6326 0.2668 0.052 Uiso 1 1 calc R . .
H20C H 0.5076 0.7232 0.2206 0.052 Uiso 1 1 calc R . .
S22 S 0.5036(5) 0.6344(2) 0.97620(16) 0.0870(9) Uani 1 1 d D . .
O22 O 0.5897(10) 0.6787(6) 1.0646(4) 0.0756(19) Uani 1 1 d . A .
C21 C 0.438(4) 0.7535(16) 0.9492(16) 0.089(3) Uani 0.50 1 d PDU A 1
H21A H 0.5492 0.7880 0.9329 0.134 Uiso 0.50 1 calc PR A 1
H21B H 0.3851 0.8100 0.9989 0.134 Uiso 0.50 1 calc PR A 1
H21C H 0.3440 0.7271 0.9012 0.134 Uiso 0.50 1 calc PR A 1
C23 C 0.262(2) 0.608(2) 1.0009(15) 0.089(3) Uani 0.50 1 d PDU A 1
H23A H 0.2539 0.5417 1.0182 0.134 Uiso 0.50 1 calc PR A 1
H23B H 0.1781 0.5929 0.9499 0.134 Uiso 0.50 1 calc PR A 1
H23C H 0.2231 0.6747 1.0477 0.134 Uiso 0.50 1 calc PR A 1
C21B C 0.547(3) 0.7508(16) 0.9398(15) 0.089(3) Uani 0.50 1 d PDU A 2
H21D H 0.6826 0.7671 0.9398 0.134 Uiso 0.50 1 calc PR A 2
H21E H 0.4902 0.8185 0.9783 0.134 Uiso 0.50 1 calc PR A 2
H21F H 0.4912 0.7301 0.8816 0.134 Uiso 0.50 1 calc PR A 2
C23B C 0.253(2) 0.622(2) 0.9739(16) 0.089(3) Uani 0.50 1 d PDU A 2
H23D H 0.2119 0.5586 0.9914 0.134 Uiso 0.50 1 calc PR A 2
H23E H 0.2019 0.6072 0.9157 0.134 Uiso 0.50 1 calc PR A 2
H23F H 0.2069 0.6927 1.0135 0.134 Uiso 0.50 1 calc PR A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0175(3) 0.0414(3) 0.0272(3) 0.0158(2) -0.0007(2) -0.0019(2)
Br2 0.0232(3) 0.0308(3) 0.0458(4) 0.0170(3) -0.0010(2) 0.0007(2)
F5 0.0365(19) 0.0280(18) 0.041(2) 0.0106(15) -0.0058(15) -0.0011(14)
F6 0.038(2) 0.040(2) 0.067(3) 0.035(2) -0.0029(18) 0.0008(16)
F7 0.075(3) 0.075(3) 0.050(3) 0.043(2) -0.008(2) 0.005(2)
F8 0.112(4) 0.058(3) 0.039(2) 0.013(2) -0.030(3) -0.009(3)
F9 0.078(3) 0.033(2) 0.050(2) 0.0149(18) -0.028(2) -0.016(2)
F12 0.052(2) 0.045(2) 0.043(2) 0.0178(18) 0.0055(18) 0.0161(18)
F13 0.075(3) 0.060(3) 0.067(3) 0.039(2) -0.021(2) 0.007(2)
F14 0.100(4) 0.089(4) 0.053(3) 0.053(3) -0.021(3) -0.029(3)
F15 0.070(3) 0.113(4) 0.056(3) 0.047(3) 0.015(2) -0.021(3)
F16 0.037(2) 0.074(3) 0.057(3) 0.035(2) 0.0088(19) -0.001(2)
N1 0.026(2) 0.026(2) 0.029(2) 0.012(2) 0.0004(19) 0.0017(19)
N2 0.031(3) 0.027(2) 0.028(2) 0.011(2) -0.001(2) 0.000(2)
C1 0.029(3) 0.029(3) 0.029(3) 0.012(2) -0.001(2) 0.003(2)
C2 0.030(3) 0.031(3) 0.034(3) 0.016(3) -0.002(2) 0.001(2)
C3 0.025(3) 0.029(3) 0.039(3) 0.016(3) -0.004(2) -0.001(2)
C4 0.026(3) 0.033(3) 0.035(3) 0.017(3) -0.006(2) 0.000(2)
C5 0.023(3) 0.034(3) 0.036(3) 0.013(3) -0.003(2) 0.002(2)
C6 0.029(3) 0.033(3) 0.051(4) 0.025(3) -0.001(3) 0.003(2)
C7 0.045(4) 0.056(4) 0.041(4) 0.030(3) -0.005(3) 0.006(3)
C8 0.058(4) 0.044(4) 0.035(4) 0.012(3) -0.017(3) -0.002(3)
C9 0.048(4) 0.029(3) 0.043(4) 0.015(3) -0.013(3) -0.005(3)
C10 0.035(3) 0.028(3) 0.029(3) 0.011(2) -0.004(2) -0.005(2)
C11 0.040(3) 0.025(3) 0.029(3) 0.011(2) -0.005(3) -0.005(2)
C12 0.048(4) 0.029(3) 0.030(3) 0.010(3) 0.001(3) -0.001(3)
C13 0.057(4) 0.035(3) 0.045(4) 0.022(3) -0.016(3) -0.002(3)
C14 0.069(5) 0.056(4) 0.042(4) 0.034(4) -0.012(4) -0.019(4)
C15 0.051(4) 0.062(5) 0.038(4) 0.025(3) 0.003(3) -0.021(4)
C16 0.037(3) 0.043(4) 0.043(4) 0.021(3) -0.003(3) -0.010(3)
C17 0.026(3) 0.030(3) 0.036(3) 0.014(3) -0.002(2) -0.002(2)
C18 0.038(3) 0.033(3) 0.029(3) 0.010(3) 0.000(3) 0.003(3)
C19 0.042(3) 0.034(3) 0.028(3) 0.011(3) 0.004(3) 0.006(3)
C20 0.027(3) 0.037(3) 0.038(3) 0.014(3) -0.008(3) -0.003(2)
S22 0.136(3) 0.0596(14) 0.0580(14) 0.0133(11) -0.0276(15) 0.0232(15)
O22 0.098(5) 0.076(4) 0.055(4) 0.031(3) -0.028(3) -0.006(4)
C21 0.102(7) 0.080(5) 0.082(6) 0.027(5) -0.039(6) 0.018(5)
C23 0.102(7) 0.080(5) 0.082(6) 0.027(5) -0.039(6) 0.018(5)
C21B 0.102(7) 0.080(5) 0.082(6) 0.027(5) -0.039(6) 0.018(5)
C23B 0.102(7) 0.080(5) 0.082(6) 0.027(5) -0.039(6) 0.018(5)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F5 C5 1.342(7) . ?
F6 C6 1.341(7) . ?
F7 C7 1.352(7) . ?
F8 C8 1.345(8) . ?
F9 C9 1.342(7) . ?
F12 C12 1.343(8) . ?
F13 C13 1.338(8) . ?
F14 C14 1.336(8) . ?
F15 C15 1.345(8) . ?
F16 C16 1.342(8) . ?
N1 C18 1.500(7) . ?
N1 C17 1.505(7) . ?
N1 C1 1.519(7) . ?
N1 C3 1.526(7) . ?
N2 C19 1.504(8) . ?
N2 C2 1.506(7) . ?
N2 C20 1.507(7) . ?
N2 C10 1.527(7) . ?
C1 C2 1.531(8) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.497(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C9 1.382(9) . ?
C4 C5 1.393(8) . ?
C5 C6 1.375(9) . ?
C6 C7 1.368(10) . ?
C7 C8 1.369(10) . ?
C8 C9 1.379(10) . ?
C10 C11 1.500(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.383(9) . ?
C11 C12 1.389(9) . ?
C12 C13 1.383(9) . ?
C13 C14 1.362(11) . ?
C14 C15 1.372(12) . ?
C15 C16 1.375(10) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
S22 O22 1.482(6) . ?
S22 C23B 1.787(15) . ?
S22 C21 1.801(14) . ?
S22 C21B 1.803(15) . ?
S22 C23 1.831(15) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 N1 C17 108.3(4) . . ?
C18 N1 C1 105.5(4) . . ?
C17 N1 C1 111.2(4) . . ?
C18 N1 C3 110.7(4) . . ?
C17 N1 C3 111.7(4) . . ?
C1 N1 C3 109.2(4) . . ?
C19 N2 C2 106.8(4) . . ?
C19 N2 C20 107.9(5) . . ?
C2 N2 C20 111.1(4) . . ?
C19 N2 C10 110.8(5) . . ?
C2 N2 C10 108.2(4) . . ?
C20 N2 C10 112.0(4) . . ?
N1 C1 C2 112.1(4) . . ?
N1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
N2 C2 C1 111.9(5) . . ?
N2 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
N2 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 N1 113.4(5) . . ?
C4 C3 H3A 108.9 . . ?
N1 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
N1 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C9 C4 C5 116.5(5) . . ?
C9 C4 C3 122.4(5) . . ?
C5 C4 C3 121.1(5) . . ?
F5 C5 C6 118.0(5) . . ?
F5 C5 C4 120.0(5) . . ?
C6 C5 C4 121.9(6) . . ?
F6 C6 C7 120.3(6) . . ?
F6 C6 C5 120.2(6) . . ?
C7 C6 C5 119.5(6) . . ?
F7 C7 C6 119.8(6) . . ?
F7 C7 C8 119.7(6) . . ?
C6 C7 C8 120.4(6) . . ?
F8 C8 C7 120.8(6) . . ?
F8 C8 C9 119.9(6) . . ?
C7 C8 C9 119.3(6) . . ?
F9 C9 C8 118.6(6) . . ?
F9 C9 C4 119.2(6) . . ?
C8 C9 C4 122.2(6) . . ?
C11 C10 N2 114.1(5) . . ?
C11 C10 H10A 108.7 . . ?
N2 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
N2 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C16 C11 C12 116.0(6) . . ?
C16 C11 C10 122.8(6) . . ?
C12 C11 C10 121.0(6) . . ?
F12 C12 C13 117.9(6) . . ?
F12 C12 C11 119.5(5) . . ?
C13 C12 C11 122.6(6) . . ?
F13 C13 C14 120.7(6) . . ?
F13 C13 C12 120.0(7) . . ?
C14 C13 C12 119.2(7) . . ?
F14 C14 C13 119.8(8) . . ?
F14 C14 C15 120.1(7) . . ?
C13 C14 C15 120.0(6) . . ?
F15 C15 C14 119.9(7) . . ?
F15 C15 C16 120.0(7) . . ?
C14 C15 C16 120.0(7) . . ?
F16 C16 C15 118.5(6) . . ?
F16 C16 C11 119.3(6) . . ?
C15 C16 C11 122.1(7) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O22 S22 C23B 112.5(9) . . ?
O22 S22 C21 108.4(8) . . ?
O22 S22 C21B 103.4(8) . . ?
C23B S22 C21B 102.1(10) . . ?
O22 S22 C23 98.7(8) . . ?
C21 S22 C23 91.0(11) . . ?
S22 C21 H21A 109.5 . . ?
S22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
S22 C23 H23A 109.5 . . ?
S22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
S22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
S22 C21B H21D 109.5 . . ?
S22 C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
S22 C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
S22 C23B H23D 109.5 . . ?
S22 C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
S22 C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 N1 C1 C2 175.4(5) . . . . ?
C17 N1 C1 C2 -67.3(6) . . . . ?
C3 N1 C1 C2 56.4(6) . . . . ?
C19 N2 C2 C1 172.6(5) . . . . ?
C20 N2 C2 C1 -70.0(6) . . . . ?
C10 N2 C2 C1 53.3(6) . . . . ?
N1 C1 C2 N2 156.3(4) . . . . ?
C18 N1 C3 C4 57.4(6) . . . . ?
C17 N1 C3 C4 -63.4(6) . . . . ?
C1 N1 C3 C4 173.2(5) . . . . ?
N1 C3 C4 C9 -90.2(7) . . . . ?
N1 C3 C4 C5 93.5(6) . . . . ?
C9 C4 C5 F5 -177.7(5) . . . . ?
C3 C4 C5 F5 -1.2(8) . . . . ?
C9 C4 C5 C6 2.6(9) . . . . ?
C3 C4 C5 C6 179.1(5) . . . . ?
F5 C5 C6 F6 -0.7(8) . . . . ?
C4 C5 C6 F6 179.0(5) . . . . ?
F5 C5 C6 C7 179.1(6) . . . . ?
C4 C5 C6 C7 -1.2(9) . . . . ?
F6 C6 C7 F7 0.2(10) . . . . ?
C5 C6 C7 F7 -179.5(6) . . . . ?
F6 C6 C7 C8 179.2(6) . . . . ?
C5 C6 C7 C8 -0.6(10) . . . . ?
F7 C7 C8 F8 1.0(11) . . . . ?
C6 C7 C8 F8 -178.0(7) . . . . ?
F7 C7 C8 C9 179.8(7) . . . . ?
C6 C7 C8 C9 0.8(11) . . . . ?
F8 C8 C9 F9 1.3(11) . . . . ?
C7 C8 C9 F9 -177.5(7) . . . . ?
F8 C8 C9 C4 179.6(7) . . . . ?
C7 C8 C9 C4 0.7(12) . . . . ?
C5 C4 C9 F9 175.9(6) . . . . ?
C3 C4 C9 F9 -0.6(10) . . . . ?
C5 C4 C9 C8 -2.4(10) . . . . ?
C3 C4 C9 C8 -178.8(6) . . . . ?
C19 N2 C10 C11 57.1(6) . . . . ?
C2 N2 C10 C11 173.9(5) . . . . ?
C20 N2 C10 C11 -63.4(7) . . . . ?
N2 C10 C11 C16 -92.7(7) . . . . ?
N2 C10 C11 C12 92.9(7) . . . . ?
C16 C11 C12 F12 179.3(5) . . . . ?
C10 C11 C12 F12 -6.0(9) . . . . ?
C16 C11 C12 C13 -0.7(9) . . . . ?
C10 C11 C12 C13 174.1(6) . . . . ?
F12 C12 C13 F13 0.6(9) . . . . ?
C11 C12 C13 F13 -179.4(6) . . . . ?
F12 C12 C13 C14 -179.1(6) . . . . ?
C11 C12 C13 C14 0.9(10) . . . . ?
F13 C13 C14 F14 -0.9(11) . . . . ?
C12 C13 C14 F14 178.7(6) . . . . ?
F13 C13 C14 C15 -179.4(7) . . . . ?
C12 C13 C14 C15 0.3(11) . . . . ?
F14 C14 C15 F15 0.5(11) . . . . ?
C13 C14 C15 F15 179.0(7) . . . . ?
F14 C14 C15 C16 179.9(7) . . . . ?
C13 C14 C15 C16 -1.6(11) . . . . ?
F15 C15 C16 F16 2.3(10) . . . . ?
C14 C15 C16 F16 -177.1(6) . . . . ?
F15 C15 C16 C11 -178.7(6) . . . . ?
C14 C15 C16 C11 1.9(11) . . . . ?
C12 C11 C16 F16 178.3(6) . . . . ?
C10 C11 C16 F16 3.6(9) . . . . ?
C12 C11 C16 C15 -0.7(9) . . . . ?
C10 C11 C16 C15 -175.3(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.924
_refine_diff_density_min         -1.087
_refine_diff_density_rms         0.129
_database_code_depnum_ccdc_archive 'CCDC 967097'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-176

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C13 H16 F3 N2), H2 O, 2(Cl)'
_chemical_formula_sum            'C26 H34 Cl2 F6 N4 O'
_chemical_formula_weight         603.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   10.5705(2)
_cell_length_b                   9.9886(3)
_cell_length_c                   26.3808(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.7420(10)
_cell_angle_gamma                90.00
_cell_volume                     2771.43(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3572
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1256
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4647
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2450
_reflns_number_gt                2119
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, et al., 2006)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0270P)²+4.8261P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2450
_refine_ls_number_parameters     180
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.33226(5) 0.54129(5) 0.168948(18) 0.02512(15) Uani 1 1 d . . .
F10 F 0.67592(11) 0.39433(14) 0.50965(4) 0.0360(3) Uani 1 1 d . . .
F11 F 0.55668(12) 0.19961(13) 0.55718(4) 0.0355(3) Uani 1 1 d . . .
F12 F 0.36437(12) 0.06314(13) 0.50675(4) 0.0360(3) Uani 1 1 d . . .
N1 N 0.29544(14) 0.42966(15) 0.34392(5) 0.0160(3) Uani 1 1 d . . .
N2 N 0.11840(15) 0.60527(17) 0.32465(6) 0.0236(4) Uani 1 1 d . . .
C1 C 0.26152(18) 0.4447(2) 0.28700(7) 0.0213(4) Uani 1 1 d . . .
H1A H 0.2167 0.3636 0.2731 0.026 Uiso 1 1 calc R . .
H1B H 0.3396 0.4564 0.2697 0.026 Uiso 1 1 calc R . .
C2 C 0.17509(19) 0.5681(2) 0.27800(7) 0.0261(5) Uani 1 1 d . . .
H2A H 0.2254 0.6442 0.2668 0.031 Uiso 1 1 calc R . .
H2B H 0.1067 0.5484 0.2506 0.031 Uiso 1 1 calc R . .
C3 C 0.06839(19) 0.4829(2) 0.34646(8) 0.0272(5) Uani 1 1 d . . .
H3A H 0.0129 0.4353 0.3199 0.033 Uiso 1 1 calc R . .
H3B H 0.0163 0.5074 0.3742 0.033 Uiso 1 1 calc R . .
C4 C 0.17671(17) 0.3894(2) 0.36753(7) 0.0209(4) Uani 1 1 d . . .
H4A H 0.1907 0.3975 0.4051 0.025 Uiso 1 1 calc R . .
H4B H 0.1547 0.2953 0.3589 0.025 Uiso 1 1 calc R . .
C5 C 0.33777(18) 0.56488(19) 0.36461(8) 0.0218(4) Uani 1 1 d . . .
H5A H 0.4041 0.6020 0.3447 0.026 Uiso 1 1 calc R . .
H5B H 0.3738 0.5565 0.4006 0.026 Uiso 1 1 calc R . .
C6 C 0.2211(2) 0.6582(2) 0.36074(8) 0.0293(5) Uani 1 1 d . . .
H6A H 0.1901 0.6677 0.3948 0.035 Uiso 1 1 calc R . .
H6B H 0.2460 0.7480 0.3494 0.035 Uiso 1 1 calc R . .
C7 C 0.39913(17) 0.32463(19) 0.35227(7) 0.0183(4) Uani 1 1 d . . .
H7A H 0.3690 0.2410 0.3349 0.022 Uiso 1 1 calc R . .
H7B H 0.4747 0.3558 0.3363 0.022 Uiso 1 1 calc R . .
C8 C 0.43814(17) 0.29431(19) 0.40773(7) 0.0175(4) Uani 1 1 d . . .
C9 C 0.53941(17) 0.3638(2) 0.43385(7) 0.0199(4) Uani 1 1 d . . .
H9 H 0.5817 0.4328 0.4174 0.024 Uiso 1 1 calc R . .
C10 C 0.57688(18) 0.3310(2) 0.48366(7) 0.0229(4) Uani 1 1 d . . .
C11 C 0.51727(19) 0.2315(2) 0.50841(7) 0.0237(4) Uani 1 1 d . . .
C12 C 0.41873(19) 0.1634(2) 0.48216(7) 0.0239(4) Uani 1 1 d . . .
C13 C 0.37838(18) 0.1921(2) 0.43218(7) 0.0205(4) Uani 1 1 d . . .
H13 H 0.3107 0.1429 0.4146 0.025 Uiso 1 1 calc R . .
O1 O 0.5000 0.7230(3) 0.2500 0.0412(6) Uani 1 2 d SD . .
H1C H 0.454(3) 0.677(3) 0.2293(9) 0.062 Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0298(3) 0.0259(3) 0.0197(2) 0.0011(2) 0.00279(19) 0.0066(2)
F10 0.0334(7) 0.0455(8) 0.0267(6) 0.0020(6) -0.0078(5) -0.0190(6)
F11 0.0464(8) 0.0403(8) 0.0182(6) 0.0066(5) -0.0054(5) -0.0131(6)
F12 0.0454(8) 0.0344(8) 0.0276(6) 0.0093(6) 0.0011(6) -0.0195(6)
N1 0.0169(8) 0.0157(8) 0.0155(8) -0.0010(6) 0.0017(6) 0.0015(7)
N2 0.0227(9) 0.0226(9) 0.0251(9) 0.0029(7) 0.0010(7) 0.0043(7)
C1 0.0232(10) 0.0266(11) 0.0140(9) 0.0005(8) 0.0009(8) 0.0025(9)
C2 0.0251(10) 0.0310(12) 0.0220(10) 0.0050(9) 0.0016(8) 0.0059(9)
C3 0.0205(10) 0.0289(12) 0.0330(11) 0.0043(10) 0.0063(8) 0.0059(9)
C4 0.0213(10) 0.0209(11) 0.0216(10) 0.0024(8) 0.0081(8) 0.0005(8)
C5 0.0226(10) 0.0159(10) 0.0262(10) -0.0045(8) -0.0011(8) 0.0006(8)
C6 0.0319(12) 0.0203(11) 0.0343(12) -0.0038(9) -0.0036(9) 0.0064(9)
C7 0.0191(10) 0.0171(10) 0.0188(9) -0.0011(8) 0.0028(7) 0.0033(8)
C8 0.0174(9) 0.0160(10) 0.0192(9) 0.0002(8) 0.0028(7) 0.0057(8)
C9 0.0185(9) 0.0186(10) 0.0233(10) 0.0015(8) 0.0052(8) -0.0002(8)
C10 0.0210(10) 0.0249(11) 0.0223(10) -0.0030(9) -0.0012(8) -0.0049(9)
C11 0.0298(11) 0.0250(11) 0.0159(9) 0.0017(8) -0.0001(8) -0.0012(9)
C12 0.0273(11) 0.0205(11) 0.0246(10) 0.0025(8) 0.0053(8) -0.0058(9)
C13 0.0187(10) 0.0200(10) 0.0224(10) -0.0034(8) -0.0001(8) -0.0010(8)
O1 0.0450(15) 0.0320(14) 0.0438(15) 0.000 -0.0092(11) 0.000

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F10 C10 1.350(2) . ?
F11 C11 1.350(2) . ?
F12 C12 1.352(2) . ?
N1 C5 1.508(2) . ?
N1 C4 1.510(2) . ?
N1 C1 1.516(2) . ?
N1 C7 1.517(2) . ?
N2 C6 1.469(3) . ?
N2 C2 1.469(3) . ?
N2 C3 1.472(3) . ?
C1 C2 1.539(3) . ?
C3 C4 1.538(3) . ?
C5 C6 1.541(3) . ?
C7 C8 1.511(2) . ?
C8 C13 1.393(3) . ?
C8 C9 1.398(3) . ?
C9 C10 1.374(3) . ?
C10 C11 1.376(3) . ?
C11 C12 1.372(3) . ?
C12 C13 1.375(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C4 108.53(14) . . ?
C5 N1 C1 107.58(14) . . ?
C4 N1 C1 108.11(14) . . ?
C5 N1 C7 112.52(14) . . ?
C4 N1 C7 111.97(14) . . ?
C1 N1 C7 107.94(13) . . ?
C6 N2 C2 107.28(16) . . ?
C6 N2 C3 108.46(16) . . ?
C2 N2 C3 108.08(16) . . ?
N1 C1 C2 108.07(15) . . ?
N2 C2 C1 111.02(15) . . ?
N2 C3 C4 111.23(16) . . ?
N1 C4 C3 107.98(15) . . ?
N1 C5 C6 108.13(15) . . ?
N2 C6 C5 111.09(16) . . ?
C8 C7 N1 113.73(14) . . ?
C13 C8 C9 119.75(17) . . ?
C13 C8 C7 120.21(17) . . ?
C9 C8 C7 119.94(17) . . ?
C10 C9 C8 119.09(18) . . ?
F10 C10 C9 120.59(18) . . ?
F10 C10 C11 117.78(17) . . ?
C9 C10 C11 121.61(18) . . ?
F11 C11 C12 120.66(18) . . ?
F11 C11 C10 120.68(17) . . ?
C12 C11 C10 118.64(18) . . ?
F12 C12 C11 117.56(17) . . ?
F12 C12 C13 120.57(18) . . ?
C11 C12 C13 121.84(18) . . ?
C12 C13 C8 119.05(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -48.08(19) . . . . ?
C4 N1 C1 C2 68.95(19) . . . . ?
C7 N1 C1 C2 -169.74(15) . . . . ?
C6 N2 C2 C1 69.9(2) . . . . ?
C3 N2 C2 C1 -46.9(2) . . . . ?
N1 C1 C2 N2 -18.8(2) . . . . ?
C6 N2 C3 C4 -46.8(2) . . . . ?
C2 N2 C3 C4 69.2(2) . . . . ?
C5 N1 C4 C3 68.67(19) . . . . ?
C1 N1 C4 C3 -47.7(2) . . . . ?
C7 N1 C4 C3 -166.52(15) . . . . ?
N2 C3 C4 N1 -18.7(2) . . . . ?
C4 N1 C5 C6 -48.0(2) . . . . ?
C1 N1 C5 C6 68.78(19) . . . . ?
C7 N1 C5 C6 -172.46(15) . . . . ?
C2 N2 C6 C5 -48.1(2) . . . . ?
C3 N2 C6 C5 68.4(2) . . . . ?
N1 C5 C6 N2 -18.2(2) . . . . ?
C5 N1 C7 C8 64.2(2) . . . . ?
C4 N1 C7 C8 -58.3(2) . . . . ?
C1 N1 C7 C8 -177.20(16) . . . . ?
N1 C7 C8 C13 91.2(2) . . . . ?
N1 C7 C8 C9 -92.4(2) . . . . ?
C13 C8 C9 C10 -1.0(3) . . . . ?
C7 C8 C9 C10 -177.34(17) . . . . ?
C8 C9 C10 F10 178.64(17) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
F10 C10 C11 F11 0.5(3) . . . . ?
C9 C10 C11 F11 179.11(18) . . . . ?
F10 C10 C11 C12 -178.15(18) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
F11 C11 C12 F12 -0.7(3) . . . . ?
C10 C11 C12 F12 177.89(18) . . . . ?
F11 C11 C12 C13 -178.70(18) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
F12 C12 C13 C8 -178.76(17) . . . . ?
C11 C12 C13 C8 -0.8(3) . . . . ?
C9 C8 C13 C12 1.4(3) . . . . ?
C7 C8 C13 C12 177.72(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1C Cl1 0.829(16) 2.373(17) 3.2017(15) 178(3) .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.046

_iucr_refine_instructions_details 
;
TITL mm-176 in C 2/c
CELL   0.71073  10.5705   9.9886  26.3808  90.000  95.742  90.000
ZERR     4       0.0002   0.0003   0.0005   0.000   0.001   0.000
LATT  7
SYMM -X,Y,1/2-Z
SFAC        C       H       N       O        F       CL
UNIT       104     136      16      4        24       8
L.S.      10
OMIT -3 50.05
OMIT 0 0 2
TEMP  -150
SIZE  0.35 0.2 0.1
ACTA
CONF
HTAB
BOND
HTAB O1 Cl1
FMAP      2
PLAN     25
WGHT    0.027000    4.826100
FVAR       0.14783
CL1   6    0.332257    0.541295    0.168948    11.00000    0.02984    0.02586 =
         0.01972    0.00110    0.00279    0.00661
F10   5    0.675923    0.394325    0.509646    11.00000    0.03344    0.04554 =
         0.02673    0.00201   -0.00778   -0.01898
F11   5    0.556682    0.199605    0.557182    11.00000    0.04640    0.04025 =
         0.01824    0.00658   -0.00536   -0.01305
F12   5    0.364372    0.063143    0.506750    11.00000    0.04544    0.03440 =
         0.02756    0.00929    0.00107   -0.01945
N1    3    0.295442    0.429661    0.343921    11.00000    0.01688    0.01571 =
         0.01546   -0.00101    0.00170    0.00151
N2    3    0.118404    0.605271    0.324649    11.00000    0.02274    0.02259 =
         0.02513    0.00285    0.00101    0.00433
C1    1    0.261516    0.444688    0.287004    11.00000    0.02324    0.02657 =
         0.01395    0.00049    0.00086    0.00247
AFIX  23
H1A   2    0.216703    0.363623    0.273083    11.00000   -1.20000
H1B   2    0.339636    0.456442    0.269679    11.00000   -1.20000
AFIX   0
C2    1    0.175093    0.568123    0.278000    11.00000    0.02513    0.03097 =
         0.02202    0.00503    0.00160    0.00588
AFIX  23
H2A   2    0.225450    0.644228    0.266794    11.00000   -1.20000
H2B   2    0.106677    0.548447    0.250583    11.00000   -1.20000
AFIX   0
C3    1    0.068392    0.482903    0.346461    11.00000    0.02047    0.02892 =
         0.03299    0.00434    0.00632    0.00594
AFIX  23
H3A   2    0.012886    0.435347    0.319856    11.00000   -1.20000
H3B   2    0.016304    0.507420    0.374221    11.00000   -1.20000
AFIX   0
C4    1    0.176710    0.389414    0.367532    11.00000    0.02127    0.02093 =
         0.02162    0.00240    0.00809    0.00046
AFIX  23
H4A   2    0.190713    0.397456    0.405078    11.00000   -1.20000
H4B   2    0.154661    0.295274    0.358869    11.00000   -1.20000
AFIX   0
C5    1    0.337765    0.564878    0.364608    11.00000    0.02264    0.01591 =
         0.02621   -0.00446   -0.00106    0.00063
AFIX  23
H5A   2    0.404115    0.601979    0.344658    11.00000   -1.20000
H5B   2    0.373814    0.556525    0.400575    11.00000   -1.20000
AFIX   0
C6    1    0.221063    0.658204    0.360736    11.00000    0.03192    0.02031 =
         0.03434   -0.00378   -0.00365    0.00644
AFIX  23
H6A   2    0.190131    0.667681    0.394757    11.00000   -1.20000
H6B   2    0.246024    0.748040    0.349398    11.00000   -1.20000
AFIX   0
C7    1    0.399127    0.324632    0.352267    11.00000    0.01915    0.01707 =
         0.01876   -0.00110    0.00281    0.00327
AFIX  23
H7A   2    0.369021    0.240962    0.334917    11.00000   -1.20000
H7B   2    0.474660    0.355780    0.336259    11.00000   -1.20000
AFIX   0
C8    1    0.438142    0.294306    0.407726    11.00000    0.01741    0.01599 =
         0.01921    0.00022    0.00282    0.00567
C9    1    0.539406    0.363843    0.433847    11.00000    0.01850    0.01860 =
         0.02328    0.00153    0.00518   -0.00017
AFIX  43
H9    2    0.581705    0.432822    0.417369    11.00000   -1.20000
AFIX   0
C10   1    0.576883    0.331044    0.483664    11.00000    0.02101    0.02485 =
         0.02230   -0.00304   -0.00122   -0.00491
C11   1    0.517269    0.231514    0.508412    11.00000    0.02983    0.02496 =
         0.01585    0.00169   -0.00007   -0.00121
C12   1    0.418731    0.163386    0.482164    11.00000    0.02726    0.02047 =
         0.02457    0.00249    0.00526   -0.00578
C13   1    0.378377    0.192090    0.432177    11.00000    0.01870    0.01997 =
         0.02242   -0.00337   -0.00008   -0.00099
AFIX  43
H13   2    0.310694    0.142895    0.414574    11.00000   -1.20000
AFIX   0
MOLE 2
O1    4    0.500000    0.722980    0.250000    10.50000    0.04497    0.03198 =
         0.04379    0.00000   -0.00921    0.00000
H1C   2    0.454489    0.677179    0.229274    11.00000   -1.50000
DFIX 0.84 O1 H1c
 
HKLF   4
 
REM  mm-176 in C 2/c
REM R1 =  0.0359 for   2119 Fo > 4sig(Fo)  and  0.0439 for all   2450 data
REM    180 parameters refined using      1 restraints
 
END
 
WGHT      0.0270      4.8257
REM Highest difference peak  0.233,  deepest hole -0.203,  1-sigma level  0.046
Q1    1   0.1744  0.6273  0.3396  11.00000  0.05    0.23
Q2    1   0.3999  0.3259  0.3867  11.00000  0.05    0.20
Q3    1   0.5315  0.2931  0.4986  11.00000  0.05    0.20
Q4    1   0.5351  0.3474  0.4598  11.00000  0.05    0.20
Q5    1   0.2147  0.5015  0.2800  11.00000  0.05    0.19
Q6    1   0.3916  0.2716  0.4232  11.00000  0.05    0.19
Q7    1   0.1391  0.5905  0.3033  11.00000  0.05    0.19
Q8    1   0.4940  0.1728  0.4925  11.00000  0.05    0.18
Q9    1   0.3531  0.3814  0.3478  11.00000  0.05    0.18
Q10   1   0.2606  0.4308  0.3184  11.00000  0.05    0.17
Q11   1   0.4787  0.3344  0.4199  11.00000  0.05    0.17
Q12   1   0.3075  0.4973  0.3553  11.00000  0.05    0.17
Q13   1   0.3398  0.5268  0.4055  11.00000  0.05    0.16
Q14   1   0.0992  0.5515  0.3388  11.00000  0.05    0.16
Q15   1   0.2808  0.1068  0.5027  11.00000  0.05    0.16
Q16   1   0.4485  0.1452  0.4570  11.00000  0.05    0.15
Q17   1   0.4033  0.1102  0.4899  11.00000  0.05    0.15
Q18   1   0.3584  0.2606  0.3438  11.00000  0.05    0.15
Q19   1   0.3589  0.2213  0.4632  11.00000  0.05    0.15
Q20   1   0.6079  0.3554  0.4897  11.00000  0.05    0.15
Q21   1   0.5364  0.2272  0.5254  11.00000  0.05    0.15
Q22   1   0.3426  0.1690  0.4248  11.00000  0.05    0.15
Q23   1   0.2874  0.6223  0.3620  11.00000  0.05    0.15
Q24   1   0.2766  0.2072  0.3272  11.00000  0.05    0.15
Q25   1   0.2784  0.4518  0.1430  11.00000  0.05    0.14
;
_database_code_depnum_ccdc_archive 'CCDC 1005267'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-aa-51

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H18 F5 N2, H2 O, Cl'
_chemical_formula_sum            'C13 H20 Cl F5 N2 O'
_chemical_formula_weight         350.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.7577(2)
_cell_length_b                   8.8912(2)
_cell_length_c                   15.3866(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.3260(10)
_cell_angle_gamma                90.00
_cell_volume                     1614.49(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4162
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9181
_exptl_absorpt_correction_T_max  0.9443
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5629
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2931
_reflns_number_gt                2602
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, et al., 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0226P)²+1.0482P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2931
_refine_ls_number_parameters     205
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0750
_refine_ls_wR_factor_gt          0.0721
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.59149(3) 0.13926(4) 0.65965(3) 0.02861(12) Uani 1 1 d . . .
F5 F 0.64578(8) 0.50172(10) 0.51980(6) 0.0273(2) Uani 1 1 d . . .
F6 F 0.70978(9) 0.25324(13) 0.45563(7) 0.0415(3) Uani 1 1 d . . .
F7 F 0.87887(10) 0.07793(12) 0.57357(8) 0.0438(3) Uani 1 1 d . . .
F8 F 0.98359(8) 0.15722(11) 0.75768(8) 0.0362(3) Uani 1 1 d . . .
F9 F 0.91630(7) 0.40311(11) 0.82344(6) 0.0289(2) Uani 1 1 d . . .
N1 N 0.83915(11) 0.80242(15) 0.88708(9) 0.0245(3) Uani 1 1 d . . .
N2 N 0.65207(10) 0.60222(14) 0.74192(8) 0.0170(3) Uani 1 1 d . . .
C1 C 0.71940(13) 0.80034(19) 0.87391(11) 0.0247(3) Uani 1 1 d . . .
H1A H 0.6987 0.9012 0.8896 0.030 Uiso 1 1 calc R . .
H1B H 0.7096 0.7281 0.9192 0.030 Uiso 1 1 calc R . .
C2 C 0.63750(13) 0.75875(17) 0.77637(11) 0.0207(3) Uani 1 1 d . . .
H2A H 0.6451 0.8336 0.7315 0.025 Uiso 1 1 calc R . .
H2B H 0.5595 0.7670 0.7749 0.025 Uiso 1 1 calc R . .
C3 C 0.74970(12) 0.60851(17) 0.70786(10) 0.0180(3) Uani 1 1 d . . .
H3A H 0.7306 0.6824 0.6560 0.022 Uiso 1 1 calc R . .
H3B H 0.8180 0.6457 0.7599 0.022 Uiso 1 1 calc R . .
C4 C 0.77792(12) 0.46115(17) 0.67405(10) 0.0184(3) Uani 1 1 d . . .
C5 C 0.72883(12) 0.41742(18) 0.58088(10) 0.0205(3) Uani 1 1 d . . .
C6 C 0.76134(14) 0.29034(19) 0.54681(11) 0.0264(4) Uani 1 1 d . . .
C7 C 0.84661(14) 0.20139(18) 0.60614(13) 0.0286(4) Uani 1 1 d . . .
C8 C 0.89797(13) 0.24104(18) 0.69933(12) 0.0257(4) Uani 1 1 d . . .
C9 C 0.86332(12) 0.36804(18) 0.73217(11) 0.0210(3) Uani 1 1 d . . .
C10 C 0.86522(15) 0.9335(2) 0.84254(13) 0.0315(4) Uani 1 1 d . . .
H10A H 0.9458 0.9326 0.8525 0.047 Uiso 1 1 calc R . .
H10B H 0.8480 1.0251 0.8701 0.047 Uiso 1 1 calc R . .
H10C H 0.8194 0.9314 0.7750 0.047 Uiso 1 1 calc R . .
C11 C 0.90982(16) 0.8002(2) 0.98749(12) 0.0376(4) Uani 1 1 d . . .
H11A H 0.8913 0.7113 1.0165 0.056 Uiso 1 1 calc R . .
H11B H 0.8956 0.8912 1.0173 0.056 Uiso 1 1 calc R . .
H11C H 0.9899 0.7967 0.9959 0.056 Uiso 1 1 calc R . .
C12 C 0.54335(12) 0.56431(18) 0.66197(11) 0.0220(3) Uani 1 1 d . . .
H12A H 0.5286 0.6391 0.6119 0.033 Uiso 1 1 calc R . .
H12B H 0.4809 0.5647 0.6843 0.033 Uiso 1 1 calc R . .
H12C H 0.5496 0.4644 0.6375 0.033 Uiso 1 1 calc R . .
C13 C 0.67285(13) 0.48633(17) 0.81735(11) 0.0213(3) Uani 1 1 d . . .
H13A H 0.7436 0.5096 0.8702 0.032 Uiso 1 1 calc R . .
H13B H 0.6787 0.3868 0.7922 0.032 Uiso 1 1 calc R . .
H13C H 0.6098 0.4868 0.8390 0.032 Uiso 1 1 calc R . .
O1 O 0.37592(14) 0.13815(16) 0.45906(10) 0.0454(4) Uani 1 1 d D . .
H1C H 0.385(2) 0.059(2) 0.4308(17) 0.068 Uiso 1 1 d D . .
H1D H 0.4354(17) 0.142(3) 0.5078(14) 0.068 Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0311(2) 0.0234(2) 0.0372(2) -0.00445(17) 0.01952(18) -0.00388(16)
F5 0.0309(5) 0.0298(5) 0.0180(4) 0.0005(4) 0.0056(4) 0.0053(4)
F6 0.0501(7) 0.0433(6) 0.0289(5) -0.0176(5) 0.0127(5) 0.0023(5)
F7 0.0486(7) 0.0291(6) 0.0597(7) -0.0132(5) 0.0274(6) 0.0077(5)
F8 0.0296(5) 0.0323(6) 0.0476(6) 0.0110(5) 0.0158(5) 0.0139(4)
F9 0.0231(5) 0.0371(6) 0.0218(5) 0.0013(4) 0.0030(4) 0.0043(4)
N1 0.0238(7) 0.0238(7) 0.0228(7) -0.0043(6) 0.0054(6) -0.0030(6)
N2 0.0169(6) 0.0165(6) 0.0176(6) -0.0005(5) 0.0063(5) -0.0014(5)
C1 0.0283(8) 0.0223(8) 0.0256(8) -0.0065(7) 0.0127(7) -0.0038(7)
C2 0.0208(7) 0.0168(8) 0.0259(8) -0.0021(6) 0.0105(6) 0.0006(6)
C3 0.0172(7) 0.0190(8) 0.0193(7) -0.0006(6) 0.0086(6) -0.0022(6)
C4 0.0176(7) 0.0176(7) 0.0223(8) -0.0002(6) 0.0103(6) -0.0030(6)
C5 0.0201(7) 0.0207(8) 0.0213(8) 0.0017(6) 0.0084(6) -0.0010(6)
C6 0.0298(9) 0.0268(9) 0.0253(8) -0.0075(7) 0.0137(7) -0.0047(7)
C7 0.0313(9) 0.0190(8) 0.0426(10) -0.0058(7) 0.0222(8) -0.0008(7)
C8 0.0199(8) 0.0224(8) 0.0371(9) 0.0068(7) 0.0134(7) 0.0039(6)
C9 0.0176(7) 0.0245(8) 0.0214(7) 0.0011(7) 0.0079(6) -0.0023(6)
C10 0.0293(9) 0.0275(9) 0.0380(10) -0.0043(8) 0.0131(8) -0.0075(7)
C11 0.0358(10) 0.0406(11) 0.0269(9) -0.0060(8) 0.0014(8) -0.0019(8)
C12 0.0174(7) 0.0243(8) 0.0216(8) -0.0035(7) 0.0042(6) -0.0027(6)
C13 0.0249(8) 0.0201(8) 0.0207(8) 0.0030(6) 0.0107(6) 0.0009(6)
O1 0.0630(10) 0.0372(8) 0.0332(7) 0.0009(6) 0.0149(7) 0.0240(7)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F5 C5 1.3458(18) . ?
F6 C6 1.3448(19) . ?
F7 C7 1.3350(19) . ?
F8 C8 1.3453(18) . ?
F9 C9 1.3436(17) . ?
N1 C10 1.453(2) . ?
N1 C1 1.463(2) . ?
N1 C11 1.463(2) . ?
N2 C13 1.4985(19) . ?
N2 C12 1.5014(18) . ?
N2 C3 1.5248(18) . ?
N2 C2 1.5256(19) . ?
C1 C2 1.513(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.503(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.384(2) . ?
C4 C9 1.390(2) . ?
C5 C6 1.374(2) . ?
C6 C7 1.374(2) . ?
C7 C8 1.377(2) . ?
C8 C9 1.377(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O1 H1C 0.853(17) . ?
O1 H1D 0.840(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C1 111.02(13) . . ?
C10 N1 C11 110.43(14) . . ?
C1 N1 C11 109.77(13) . . ?
C13 N2 C12 108.46(11) . . ?
C13 N2 C3 111.36(11) . . ?
C12 N2 C3 110.35(11) . . ?
C13 N2 C2 111.54(11) . . ?
C12 N2 C2 107.03(11) . . ?
C3 N2 C2 108.02(11) . . ?
N1 C1 C2 115.58(13) . . ?
N1 C1 H1A 108.4 . . ?
C2 C1 H1A 108.4 . . ?
N1 C1 H1B 108.4 . . ?
C2 C1 H1B 108.4 . . ?
H1A C1 H1B 107.4 . . ?
C1 C2 N2 115.99(12) . . ?
C1 C2 H2A 108.3 . . ?
N2 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
N2 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
C4 C3 N2 114.92(12) . . ?
C4 C3 H3A 108.5 . . ?
N2 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
N2 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C5 C4 C9 115.77(14) . . ?
C5 C4 C3 121.98(13) . . ?
C9 C4 C3 121.92(13) . . ?
F5 C5 C6 117.58(13) . . ?
F5 C5 C4 119.55(13) . . ?
C6 C5 C4 122.86(14) . . ?
F6 C6 C7 120.13(15) . . ?
F6 C6 C5 120.05(15) . . ?
C7 C6 C5 119.81(15) . . ?
F7 C7 C6 120.20(16) . . ?
F7 C7 C8 120.59(16) . . ?
C6 C7 C8 119.21(15) . . ?
F8 C8 C9 120.13(15) . . ?
F8 C8 C7 119.85(15) . . ?
C9 C8 C7 120.01(15) . . ?
F9 C9 C8 118.02(14) . . ?
F9 C9 C4 119.63(14) . . ?
C8 C9 C4 122.34(14) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H1C O1 H1D 104(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C1 C2 74.07(17) . . . . ?
C11 N1 C1 C2 -163.56(14) . . . . ?
N1 C1 C2 N2 61.38(18) . . . . ?
C13 N2 C2 C1 42.81(17) . . . . ?
C12 N2 C2 C1 161.30(13) . . . . ?
C3 N2 C2 C1 -79.88(15) . . . . ?
C13 N2 C3 C4 55.38(16) . . . . ?
C12 N2 C3 C4 -65.14(16) . . . . ?
C2 N2 C3 C4 178.18(12) . . . . ?
N2 C3 C4 C5 91.13(16) . . . . ?
N2 C3 C4 C9 -95.76(16) . . . . ?
C9 C4 C5 F5 -179.73(13) . . . . ?
C3 C4 C5 F5 -6.2(2) . . . . ?
C9 C4 C5 C6 0.0(2) . . . . ?
C3 C4 C5 C6 173.55(14) . . . . ?
F5 C5 C6 F6 -0.7(2) . . . . ?
C4 C5 C6 F6 179.53(14) . . . . ?
F5 C5 C6 C7 179.30(14) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
F6 C6 C7 F7 0.1(2) . . . . ?
C5 C6 C7 F7 -179.86(14) . . . . ?
F6 C6 C7 C8 -179.73(15) . . . . ?
C5 C6 C7 C8 0.3(2) . . . . ?
F7 C7 C8 F8 1.9(2) . . . . ?
C6 C7 C8 F8 -178.24(14) . . . . ?
F7 C7 C8 C9 -179.52(14) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
F8 C8 C9 F9 -0.9(2) . . . . ?
C7 C8 C9 F9 -179.54(14) . . . . ?
F8 C8 C9 C4 177.77(14) . . . . ?
C7 C8 C9 C4 -0.8(2) . . . . ?
C5 C4 C9 F9 179.31(13) . . . . ?
C3 C4 C9 F9 5.8(2) . . . . ?
C5 C4 C9 C8 0.6(2) . . . . ?
C3 C4 C9 C8 -172.91(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1C Cl1 0.853(17) 2.339(17) 3.1890(14) 174(2) 3_656
O1 H1D Cl1 0.840(17) 2.427(17) 3.2620(15) 172(2) .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.041

_iucr_refine_instructions_details 
;
TITL mm-aa-51 in P 21/c
CELL   0.71073  12.7577   8.8912  15.3866  90.000 112.326  90.000
ZERR     4       0.0002   0.0002   0.0003   0.000   0.001   0.000
LATT  1
SYMM -X,1/2+Y,1/2-Z
SFAC        C       H       N       O       F       CL
UNIT        52      80      8       4       20      4
L.S.      10
OMIT -3 50.5
TEMP  -150
SIZE  0.30 0.27 0.20
EQIV $1 -x+1, -y, -z+1
HTAB O1 Cl1_$1
HTAB O1 Cl1
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.022600    1.048200
FVAR       0.68305
MOLE 1
CL1   6    0.591491    0.139257    0.659651    11.00000    0.03108    0.02336 =
         0.03720   -0.00445    0.01952   -0.00388
F5    5    0.645776    0.501717    0.519804    11.00000    0.03086    0.02981 =
         0.01797    0.00051    0.00565    0.00532
F6    5    0.709783    0.253238    0.455627    11.00000    0.05005    0.04334 =
         0.02891   -0.01764    0.01266    0.00234
F7    5    0.878865    0.077927    0.573566    11.00000    0.04864    0.02909 =
         0.05971   -0.01320    0.02742    0.00766
F8    5    0.983593    0.157223    0.757684    11.00000    0.02959    0.03228 =
         0.04763    0.01096    0.01582    0.01387
F9    5    0.916303    0.403114    0.823438    11.00000    0.02305    0.03711 =
         0.02177    0.00134    0.00302    0.00429
N1    3    0.839153    0.802420    0.887080    11.00000    0.02378    0.02383 =
         0.02279   -0.00428    0.00539   -0.00300
N2    3    0.652073    0.602221    0.741916    11.00000    0.01686    0.01647 =
         0.01756   -0.00053    0.00631   -0.00143
C1    1    0.719405    0.800345    0.873914    11.00000    0.02827    0.02227 =
         0.02561   -0.00653    0.01267   -0.00383
AFIX  23
H1A   2    0.698748    0.901220    0.889565    11.00000   -1.20000
H1B   2    0.709593    0.728123    0.919212    11.00000   -1.20000
AFIX   0
C2    1    0.637497    0.758746    0.776375    11.00000    0.02084    0.01684 =
         0.02594   -0.00213    0.01047    0.00063
AFIX  23
H2A   2    0.645095    0.833607    0.731497    11.00000   -1.20000
H2B   2    0.559469    0.766950    0.774943    11.00000   -1.20000
AFIX   0
C3    1    0.749704    0.608509    0.707857    11.00000    0.01718    0.01903 =
         0.01929   -0.00061    0.00856   -0.00218
AFIX  23
H3A   2    0.730590    0.682437    0.656011    11.00000   -1.20000
H3B   2    0.818049    0.645722    0.759874    11.00000   -1.20000
AFIX   0
C4    1    0.777922    0.461148    0.674048    11.00000    0.01758    0.01760 =
         0.02234   -0.00022    0.01032   -0.00296
C5    1    0.728830    0.417423    0.580884    11.00000    0.02014    0.02071 =
         0.02126    0.00169    0.00844   -0.00104
C6    1    0.761335    0.290342    0.546806    11.00000    0.02984    0.02680 =
         0.02532   -0.00749    0.01371   -0.00475
C7    1    0.846612    0.201393    0.606143    11.00000    0.03126    0.01903 =
         0.04265   -0.00582    0.02222   -0.00084
C8    1    0.897967    0.241042    0.699328    11.00000    0.01994    0.02237 =
         0.03712    0.00676    0.01344    0.00394
C9    1    0.863322    0.368043    0.732165    11.00000    0.01757    0.02453 =
         0.02142    0.00110    0.00787   -0.00235
C10   1    0.865219    0.933543    0.842538    11.00000    0.02931    0.02754 =
         0.03796   -0.00428    0.01312   -0.00746
AFIX  33
H10A  2    0.945797    0.932589    0.852530    11.00000   -1.50000
H10B  2    0.848001    1.025068    0.870056    11.00000   -1.50000
H10C  2    0.819434    0.931381    0.774995    11.00000   -1.50000
AFIX   0
C11   1    0.909822    0.800210    0.987486    11.00000    0.03581    0.04061 =
         0.02695   -0.00597    0.00137   -0.00193
AFIX  33
H11A  2    0.891310    0.711282    1.016503    11.00000   -1.50000
H11B  2    0.895595    0.891180    1.017273    11.00000   -1.50000
H11C  2    0.989884    0.796688    0.995919    11.00000   -1.50000
AFIX   0
C12   1    0.543348    0.564314    0.661975    11.00000    0.01740    0.02426 =
         0.02162   -0.00348    0.00421   -0.00271
AFIX  33
H12A  2    0.528584    0.639111    0.611934    11.00000   -1.50000
H12B  2    0.480889    0.564731    0.684273    11.00000   -1.50000
H12C  2    0.549606    0.464357    0.637539    11.00000   -1.50000
AFIX   0
C13   1    0.672849    0.486329    0.817348    11.00000    0.02485    0.02013 =
         0.02073    0.00296    0.01066    0.00088
AFIX  33
H13A  2    0.743579    0.509606    0.870167    11.00000   -1.50000
H13B  2    0.678734    0.386772    0.792245    11.00000   -1.50000
H13C  2    0.609821    0.486815    0.838965    11.00000   -1.50000
AFIX   0
MOLE 2
O1    4    0.375922    0.138150    0.459059    11.00000    0.06295    0.03721 =
         0.03319    0.00086    0.01490    0.02398
H1C   2    0.384688    0.059486    0.430759    11.00000   -1.50000
H1D   2    0.435364    0.142146    0.507781    11.00000   -1.50000
DFIX 0.84 O1 H1C O1 H1D
HKLF   4
 
REM  mm-aa-51 in P 21/c
REM R1 =  0.0311 for   2602 Fo > 4sig(Fo)  and  0.0365 for all   2931 data
REM    205 parameters refined using      2 restraints
 
END
 
WGHT      0.0226      1.0511
REM Highest difference peak  0.236,  deepest hole -0.203,  1-sigma level  0.041
Q1    1   0.8996  0.3186  0.7084  11.00000  0.05    0.24
Q2    1   0.7643  0.5204  0.6895  11.00000  0.05    0.22
Q3    1   0.6600  0.5470  0.7790  11.00000  0.05    0.20
Q4    1   0.7063  0.5976  0.7299  11.00000  0.05    0.20
Q5    1   0.7758  0.4570  0.6343  11.00000  0.05    0.20
Q6    1   0.7832  0.2202  0.5822  11.00000  0.05    0.20
Q7    1   0.7356  0.4250  0.6396  11.00000  0.05    0.20
Q8    1   0.7796  0.7993  0.8782  11.00000  0.05    0.19
Q9    1   0.8012  0.3970  0.7046  11.00000  0.05    0.19
Q10   1   0.8297  0.4301  0.6908  11.00000  0.05    0.18
Q11   1   0.8449  0.2017  0.6556  11.00000  0.05    0.18
Q12   1   0.8913  0.2473  0.6544  11.00000  0.05    0.18
Q13   1   0.7219  0.3283  0.5697  11.00000  0.05    0.18
Q14   1   0.6019  0.5801  0.7045  11.00000  0.05    0.18
Q15   1   0.8276  0.2773  0.5721  11.00000  0.05    0.16
Q16   1   0.6517  0.6766  0.7638  11.00000  0.05    0.16
Q17   1   0.5496  0.1816  0.5907  11.00000  0.05    0.15
Q18   1   0.8553  0.7239  0.8748  11.00000  0.05    0.15
Q19   1   0.8535  0.8549  0.8708  11.00000  0.05    0.15
Q20   1   0.8604  0.2736  0.7153  11.00000  0.05    0.15
Q21   1   0.8659  0.7999  0.9333  11.00000  0.05    0.14
Q22   1   0.5020  0.1777  0.6258  11.00000  0.05    0.13
Q23   1   0.6825  0.7588  0.8275  11.00000  0.05    0.13
Q24   1   0.5599  0.2539  0.6566  11.00000  0.05    0.12
Q25   1   0.6205  0.2270  0.6276  11.00000  0.05    0.11
;
_database_code_depnum_ccdc_archive 'CCDC 1005268'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-239

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H18 F4 N, Br'
_chemical_formula_sum            'C13 H18 Br F4 N'
_chemical_formula_weight         344.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.9686(2)
_cell_length_b                   8.1122(2)
_cell_length_c                   14.4871(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.7290(10)
_cell_angle_gamma                90.00
_cell_volume                     1425.44(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3684
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    2.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4751
_exptl_absorpt_correction_T_max  0.5933
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4641
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2573
_reflns_number_gt                2157
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, et al., 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0175P)²+1.2664P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2573
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0574
_refine_ls_wR_factor_gt          0.0539
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.683828(16) 0.00440(3) 0.398617(15) 0.02580(9) Uani 1 1 d . . .
F9 F 0.96383(9) 0.57644(15) 0.34536(9) 0.0246(3) Uani 1 1 d . . .
F10 F 1.12528(10) 0.42963(19) 0.48980(9) 0.0344(3) Uani 1 1 d . . .
F12 F 0.98057(11) -0.08973(16) 0.36251(10) 0.0333(3) Uani 1 1 d . . .
F13 F 0.82491(10) 0.05705(15) 0.21225(9) 0.0255(3) Uani 1 1 d . . .
N1 N 0.68949(13) 0.4348(2) 0.20331(12) 0.0154(3) Uani 1 1 d . . .
C1 C 0.70767(17) 0.4834(3) 0.30960(14) 0.0215(5) Uani 1 1 d . . .
H1A H 0.7489 0.3940 0.3538 0.026 Uiso 1 1 calc R . .
H1B H 0.7543 0.5836 0.3261 0.026 Uiso 1 1 calc R . .
C2 C 0.60287(18) 0.5168(3) 0.33034(17) 0.0306(6) Uani 1 1 d . . .
H2A H 0.6217 0.5473 0.3998 0.046 Uiso 1 1 calc R . .
H2B H 0.5570 0.4174 0.3163 0.046 Uiso 1 1 calc R . .
H2C H 0.5622 0.6073 0.2883 0.046 Uiso 1 1 calc R . .
C3 C 0.62048(16) 0.2786(3) 0.17909(15) 0.0204(4) Uani 1 1 d . . .
H3A H 0.6580 0.1934 0.2285 0.024 Uiso 1 1 calc R . .
H3B H 0.5486 0.3019 0.1859 0.024 Uiso 1 1 calc R . .
C4 C 0.59927(18) 0.2085(3) 0.07683(16) 0.0258(5) Uani 1 1 d . . .
H4A H 0.5544 0.1084 0.0679 0.039 Uiso 1 1 calc R . .
H4B H 0.6697 0.1816 0.0696 0.039 Uiso 1 1 calc R . .
H4C H 0.5600 0.2902 0.0269 0.039 Uiso 1 1 calc R . .
C5 C 0.62866(16) 0.5696(3) 0.13079(14) 0.0185(4) Uani 1 1 d . . .
H5A H 0.6310 0.5422 0.0650 0.022 Uiso 1 1 calc R . .
H5B H 0.5503 0.5690 0.1252 0.022 Uiso 1 1 calc R . .
C6 C 0.67392(18) 0.7428(3) 0.15798(17) 0.0271(5) Uani 1 1 d . . .
H6A H 0.6300 0.8207 0.1077 0.041 Uiso 1 1 calc R . .
H6B H 0.7508 0.7464 0.1616 0.041 Uiso 1 1 calc R . .
H6C H 0.6702 0.7731 0.2222 0.041 Uiso 1 1 calc R . .
C7 C 0.80090(15) 0.4105(3) 0.19197(14) 0.0165(4) Uani 1 1 d . . .
H7A H 0.7893 0.3480 0.1304 0.020 Uiso 1 1 calc R . .
H7B H 0.8306 0.5200 0.1844 0.020 Uiso 1 1 calc R . .
C8 C 0.88603(15) 0.3216(3) 0.27594(14) 0.0165(4) Uani 1 1 d . . .
C9 C 0.96602(16) 0.4105(3) 0.34862(15) 0.0179(4) Uani 1 1 d . . .
C10 C 1.04876(16) 0.3335(3) 0.42352(15) 0.0228(5) Uani 1 1 d . . .
C11 C 1.05548(17) 0.1652(3) 0.43132(16) 0.0256(5) Uani 1 1 d . . .
H11 H 1.1120 0.1124 0.4837 0.031 Uiso 1 1 calc R . .
C12 C 0.97676(17) 0.0764(3) 0.35999(16) 0.0217(5) Uani 1 1 d . . .
C13 C 0.89518(16) 0.1516(3) 0.28319(15) 0.0187(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02240(12) 0.03643(14) 0.01848(12) 0.00620(10) 0.00712(9) 0.00703(10)
F9 0.0226(6) 0.0199(6) 0.0289(7) -0.0030(5) 0.0062(5) -0.0037(5)
F10 0.0231(6) 0.0467(9) 0.0244(7) -0.0093(6) -0.0026(5) -0.0005(6)
F12 0.0400(8) 0.0222(7) 0.0426(8) 0.0073(6) 0.0207(7) 0.0113(6)
F13 0.0242(6) 0.0208(6) 0.0313(7) -0.0075(5) 0.0094(6) -0.0032(5)
N1 0.0145(8) 0.0187(9) 0.0131(8) 0.0018(7) 0.0049(7) 0.0000(7)
C1 0.0174(10) 0.0335(13) 0.0123(9) -0.0006(9) 0.0038(8) 0.0036(9)
C2 0.0222(11) 0.0488(16) 0.0218(11) -0.0008(11) 0.0091(9) 0.0099(11)
C3 0.0184(10) 0.0194(11) 0.0239(11) 0.0051(9) 0.0082(9) -0.0021(9)
C4 0.0247(11) 0.0229(12) 0.0229(11) -0.0009(9) -0.0003(9) -0.0077(9)
C5 0.0176(10) 0.0189(11) 0.0158(10) 0.0027(8) 0.0020(8) 0.0012(9)
C6 0.0297(12) 0.0178(11) 0.0307(13) 0.0002(10) 0.0066(10) 0.0001(9)
C7 0.0132(9) 0.0210(11) 0.0162(10) 0.0010(8) 0.0064(8) -0.0009(8)
C8 0.0139(9) 0.0215(11) 0.0157(10) 0.0007(8) 0.0073(8) 0.0010(8)
C9 0.0174(10) 0.0181(11) 0.0195(10) -0.0011(8) 0.0082(9) 0.0002(8)
C10 0.0157(10) 0.0352(13) 0.0162(10) -0.0073(9) 0.0039(8) -0.0017(9)
C11 0.0215(11) 0.0379(14) 0.0184(11) 0.0052(10) 0.0082(9) 0.0120(10)
C12 0.0256(11) 0.0180(11) 0.0278(12) 0.0035(9) 0.0172(10) 0.0062(9)
C13 0.0173(10) 0.0222(11) 0.0196(10) -0.0041(9) 0.0101(9) -0.0012(8)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F9 C9 1.347(2) . ?
F10 C10 1.357(2) . ?
F12 C12 1.349(3) . ?
F13 C13 1.346(2) . ?
N1 C3 1.519(3) . ?
N1 C7 1.524(2) . ?
N1 C1 1.525(2) . ?
N1 C5 1.528(3) . ?
C1 C2 1.516(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.518(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.520(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.506(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.385(3) . ?
C8 C9 1.390(3) . ?
C9 C10 1.377(3) . ?
C10 C11 1.370(3) . ?
C11 C12 1.372(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C7 111.76(15) . . ?
C3 N1 C1 108.47(15) . . ?
C7 N1 C1 109.20(14) . . ?
C3 N1 C5 108.63(15) . . ?
C7 N1 C5 107.29(14) . . ?
C1 N1 C5 111.52(16) . . ?
C2 C1 N1 114.66(16) . . ?
C2 C1 H1A 108.6 . . ?
N1 C1 H1A 108.6 . . ?
C2 C1 H1B 108.6 . . ?
N1 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 N1 115.24(16) . . ?
C4 C3 H3A 108.5 . . ?
N1 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
N1 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N1 115.16(16) . . ?
C6 C5 H5A 108.5 . . ?
N1 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
N1 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N1 115.28(15) . . ?
C8 C7 H7A 108.5 . . ?
N1 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
N1 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C13 C8 C9 116.01(18) . . ?
C13 C8 C7 123.83(18) . . ?
C9 C8 C7 120.03(19) . . ?
F9 C9 C10 118.83(18) . . ?
F9 C9 C8 119.43(18) . . ?
C10 C9 C8 121.7(2) . . ?
F10 C10 C11 120.3(2) . . ?
F10 C10 C9 117.9(2) . . ?
C11 C10 C9 121.8(2) . . ?
C10 C11 C12 116.9(2) . . ?
C10 C11 H11 121.6 . . ?
C12 C11 H11 121.6 . . ?
F12 C12 C11 119.58(19) . . ?
F12 C12 C13 118.33(19) . . ?
C11 C12 C13 122.1(2) . . ?
F13 C13 C12 118.94(19) . . ?
F13 C13 C8 119.52(18) . . ?
C12 C13 C8 121.52(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 C2 -59.8(2) . . . . ?
C7 N1 C1 C2 178.19(18) . . . . ?
C5 N1 C1 C2 59.8(2) . . . . ?
C7 N1 C3 C4 -56.7(2) . . . . ?
C1 N1 C3 C4 -177.19(17) . . . . ?
C5 N1 C3 C4 61.4(2) . . . . ?
C3 N1 C5 C6 167.41(17) . . . . ?
C7 N1 C5 C6 -71.6(2) . . . . ?
C1 N1 C5 C6 47.9(2) . . . . ?
C3 N1 C7 C8 -78.5(2) . . . . ?
C1 N1 C7 C8 41.5(2) . . . . ?
C5 N1 C7 C8 162.54(17) . . . . ?
N1 C7 C8 C13 85.6(2) . . . . ?
N1 C7 C8 C9 -98.8(2) . . . . ?
C13 C8 C9 F9 178.69(18) . . . . ?
C7 C8 C9 F9 2.7(3) . . . . ?
C13 C8 C9 C10 -0.4(3) . . . . ?
C7 C8 C9 C10 -176.40(18) . . . . ?
F9 C9 C10 F10 -1.0(3) . . . . ?
C8 C9 C10 F10 178.15(17) . . . . ?
F9 C9 C10 C11 179.73(19) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
F10 C10 C11 C12 -178.29(18) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C10 C11 C12 F12 178.52(19) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
F12 C12 C13 F13 -2.1(3) . . . . ?
C11 C12 C13 F13 175.71(18) . . . . ?
F12 C12 C13 C8 179.83(18) . . . . ?
C11 C12 C13 C8 -2.3(3) . . . . ?
C9 C8 C13 F13 -175.93(16) . . . . ?
C7 C8 C13 F13 -0.1(3) . . . . ?
C9 C8 C13 C12 2.1(3) . . . . ?
C7 C8 C13 C12 177.92(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.053

_iucr_refine_instructions_details 
;
TITL mm-239 in P 21/c
CELL   0.71073  12.9686   8.1122  14.4871  90.000 110.729  90.000
ZERR     4       0.0002   0.0002   0.0003   0.000   0.001   0.000
LATT  1
SYMM -X,1/2+Y,1/2-Z
SFAC        C       H       N       F       BR
UNIT        52      72       4      16       4
OMIT -3 50.5
OMIT 6 2 2
L.S.      10
TEMP  -150
SIZE  0.30 0.22 0.20
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.017500    1.266400
FVAR       0.62178
BR1   5    0.683828    0.004398    0.398617    11.00000    0.02240    0.03643 =
         0.01848    0.00620    0.00712    0.00703
F9    4    0.963834    0.576443    0.345363    11.00000    0.02255    0.01994 =
         0.02891   -0.00302    0.00623   -0.00372
F10   4    1.125283    0.429630    0.489803    11.00000    0.02309    0.04675 =
         0.02440   -0.00929   -0.00262   -0.00050
F12   4    0.980565   -0.089732    0.362505    11.00000    0.03996    0.02216 =
         0.04259    0.00726    0.02068    0.01134
F13   4    0.824909    0.057054    0.212251    11.00000    0.02417    0.02080 =
         0.03132   -0.00752    0.00944   -0.00325
N1    3    0.689491    0.434823    0.203307    11.00000    0.01452    0.01866 =
         0.01315    0.00182    0.00491   -0.00003
C1    1    0.707667    0.483440    0.309600    11.00000    0.01740    0.03349 =
         0.01233   -0.00059    0.00381    0.00358
AFIX  23
H1A   2    0.748878    0.393996    0.353817    11.00000   -1.20000
H1B   2    0.754256    0.583598    0.326090    11.00000   -1.20000
AFIX   0
C2    1    0.602870    0.516794    0.330345    11.00000    0.02222    0.04877 =
         0.02182   -0.00082    0.00914    0.00992
AFIX  33
H2A   2    0.621732    0.547285    0.399844    11.00000   -1.50000
H2B   2    0.556957    0.417392    0.316302    11.00000   -1.50000
H2C   2    0.562199    0.607258    0.288295    11.00000   -1.50000
AFIX   0
C3    1    0.620476    0.278634    0.179087    11.00000    0.01844    0.01942 =
         0.02390    0.00512    0.00824   -0.00210
AFIX  23
H3A   2    0.657989    0.193443    0.228495    11.00000   -1.20000
H3B   2    0.548559    0.301920    0.185872    11.00000   -1.20000
AFIX   0
C4    1    0.599270    0.208479    0.076834    11.00000    0.02467    0.02289 =
         0.02287   -0.00094   -0.00029   -0.00771
AFIX  33
H4A   2    0.554447    0.108410    0.067909    11.00000   -1.50000
H4B   2    0.669716    0.181590    0.069647    11.00000   -1.50000
H4C   2    0.559959    0.290159    0.026949    11.00000   -1.50000
AFIX   0
C5    1    0.628656    0.569614    0.130786    11.00000    0.01761    0.01892 =
         0.01577    0.00273    0.00196    0.00119
AFIX  23
H5A   2    0.630971    0.542163    0.064962    11.00000   -1.20000
H5B   2    0.550350    0.568954    0.125250    11.00000   -1.20000
AFIX   0
C6    1    0.673921    0.742808    0.157980    11.00000    0.02969    0.01776 =
         0.03068    0.00020    0.00663    0.00012
AFIX  33
H6A   2    0.629978    0.820651    0.107692    11.00000   -1.50000
H6B   2    0.750782    0.746376    0.161570    11.00000   -1.50000
H6C   2    0.670191    0.773067    0.222214    11.00000   -1.50000
AFIX   0
C7    1    0.800898    0.410486    0.191970    11.00000    0.01320    0.02098 =
         0.01620    0.00104    0.00638   -0.00093
AFIX  23
H7A   2    0.789346    0.348033    0.130402    11.00000   -1.20000
H7B   2    0.830602    0.520042    0.184412    11.00000   -1.20000
AFIX   0
C8    1    0.886031    0.321575    0.275943    11.00000    0.01388    0.02148 =
         0.01567    0.00075    0.00731    0.00104
C9    1    0.966024    0.410526    0.348621    11.00000    0.01737    0.01813 =
         0.01953   -0.00106    0.00818    0.00024
C10   1    1.048763    0.333490    0.423523    11.00000    0.01565    0.03515 =
         0.01622   -0.00732    0.00390   -0.00167
C11   1    1.055480    0.165163    0.431319    11.00000    0.02147    0.03791 =
         0.01838    0.00515    0.00822    0.01200
AFIX  43
H11   2    1.112013    0.112393    0.483681    11.00000   -1.20000
AFIX   0
C12   1    0.976765    0.076440    0.359986    11.00000    0.02562    0.01803 =
         0.02778    0.00352    0.01724    0.00623
C13   1    0.895178    0.151568    0.283192    11.00000    0.01729    0.02222 =
         0.01959   -0.00414    0.01012   -0.00118
HKLF   4
 
REM  mm-239 in P 21/c
REM R1 =  0.0242 for   2157 Fo > 4sig(Fo)  and  0.0322 for all   2573 data
REM    172 parameters refined using      0 restraints
 
END
 
WGHT      0.0175      1.2712
REM Highest difference peak  0.267,  deepest hole -0.287,  1-sigma level  0.053
Q1    1   0.5756  0.4183  0.3630  11.00000  0.05    0.27
Q2    1   0.5370  0.5347  0.2776  11.00000  0.05    0.26
Q3    1   0.8548  0.3587  0.2367  11.00000  0.05    0.24
Q4    1   0.6201  0.6049  0.3796  11.00000  0.05    0.23
Q5    1   0.6134  0.2866  0.0212  11.00000  0.05    0.23
Q6    1   0.9358  0.3573  0.2963  11.00000  0.05    0.21
Q7    1   0.6488  0.6516  0.1460  11.00000  0.05    0.21
Q8    1   0.7427  0.4051  0.1916  11.00000  0.05    0.19
Q9    1   0.6154  0.8260  0.0581  11.00000  0.05    0.19
Q10   1   0.6770  0.5142  0.1810  11.00000  0.05    0.19
Q11   1   0.9134  0.2510  0.2640  11.00000  0.05    0.19
Q12   1   0.8941  0.3524  0.3212  11.00000  0.05    0.18
Q13   1   0.9944  0.3695  0.3994  11.00000  0.05    0.18
Q14   1   0.6381  0.7822  0.1833  11.00000  0.05    0.18
Q15   1   0.8767  0.2409  0.2846  11.00000  0.05    0.18
Q16   1   0.6827  0.0955  0.0758  11.00000  0.05    0.17
Q17   1   1.1362  0.5795  0.4939  11.00000  0.05    0.17
Q18   1   1.0267  0.2636  0.4392  11.00000  0.05    0.17
Q19   1   0.7109  0.4639  0.2620  11.00000  0.05    0.17
Q20   1   0.8230  0.2722  0.4801  11.00000  0.05    0.16
Q21   1   0.6582  0.1265  0.3379  11.00000  0.05    0.16
Q22   1   0.6216  0.2557  0.1348  11.00000  0.05    0.16
Q23   1   0.9385  0.1246  0.3120  11.00000  0.05    0.15
Q24   1   0.9147 -0.1212  0.3256  11.00000  0.05    0.15
Q25   1   0.5820 -0.1038  0.3640  11.00000  0.05    0.15
;
_database_code_depnum_ccdc_archive 'CCDC 1005269'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-234-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H19 F3 N, Br'
_chemical_formula_sum            'C13 H19 Br F3 N'
_chemical_formula_weight         326.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.75180(10)
_cell_length_b                   10.4214(2)
_cell_length_c                   17.7318(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.5560(10)
_cell_angle_gamma                90.00
_cell_volume                     1408.21(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3565
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    2.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4729
_exptl_absorpt_correction_T_max  0.6509
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8157
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2495
_reflns_number_gt                2222
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, et al., 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0140P)²+0.9143P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2495
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0216
_refine_ls_wR_factor_ref         0.0501
_refine_ls_wR_factor_gt          0.0486
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.01079(2) 0.634831(19) 0.691653(11) 0.02151(8) Uani 1 1 d . . .
F9 F 0.53520(15) 0.48613(12) 0.71941(6) 0.0273(3) Uani 1 1 d . . .
F11 F 0.12593(17) 0.25515(12) 0.54444(7) 0.0354(3) Uani 1 1 d . . .
F13 F 0.31893(16) 0.65607(11) 0.47545(6) 0.0259(3) Uani 1 1 d . . .
N1 N 0.4879(2) 0.80848(16) 0.65381(9) 0.0174(3) Uani 1 1 d . . .
C1 C 0.3177(3) 0.85269(19) 0.60383(11) 0.0202(4) Uani 1 1 d . . .
H1A H 0.3387 0.8644 0.5509 0.024 Uiso 1 1 calc R . .
H1B H 0.2296 0.7835 0.6025 0.024 Uiso 1 1 calc R . .
C2 C 0.2402(3) 0.9755(2) 0.62865(13) 0.0334(5) Uani 1 1 d . . .
H2A H 0.1310 0.9953 0.5931 0.050 Uiso 1 1 calc R . .
H2B H 0.3239 1.0459 0.6283 0.050 Uiso 1 1 calc R . .
H2C H 0.2156 0.9648 0.6806 0.050 Uiso 1 1 calc R . .
C3 C 0.6331(3) 0.9089(2) 0.66243(11) 0.0228(4) Uani 1 1 d . . .
H3A H 0.6056 0.9772 0.6972 0.027 Uiso 1 1 calc R . .
H3B H 0.7443 0.8681 0.6873 0.027 Uiso 1 1 calc R . .
C4 C 0.6613(3) 0.9708(2) 0.58819(13) 0.0357(6) Uani 1 1 d . . .
H4A H 0.7569 1.0334 0.5992 0.053 Uiso 1 1 calc R . .
H4B H 0.5534 1.0143 0.5637 0.053 Uiso 1 1 calc R . .
H4C H 0.6918 0.9046 0.5536 0.053 Uiso 1 1 calc R . .
C5 C 0.4512(3) 0.7787(2) 0.73369(10) 0.0200(4) Uani 1 1 d . . .
H5A H 0.3870 0.8521 0.7508 0.024 Uiso 1 1 calc R . .
H5B H 0.3731 0.7029 0.7300 0.024 Uiso 1 1 calc R . .
C6 C 0.6125(3) 0.7524(2) 0.79438(11) 0.0253(5) Uani 1 1 d . . .
H6A H 0.5766 0.7338 0.8434 0.038 Uiso 1 1 calc R . .
H6B H 0.6892 0.8280 0.8001 0.038 Uiso 1 1 calc R . .
H6C H 0.6761 0.6786 0.7788 0.038 Uiso 1 1 calc R . .
C7 C 0.5543(2) 0.69058(19) 0.61680(11) 0.0194(4) Uani 1 1 d . . .
H7A H 0.5886 0.7176 0.5681 0.023 Uiso 1 1 calc R . .
H7B H 0.6617 0.6596 0.6510 0.023 Uiso 1 1 calc R . .
C8 C 0.4291(2) 0.57983(19) 0.59989(11) 0.0180(4) Uani 1 1 d . . .
C9 C 0.4292(3) 0.47758(19) 0.64978(11) 0.0205(4) Uani 1 1 d . . .
C10 C 0.3321(3) 0.3672(2) 0.63399(12) 0.0233(5) Uani 1 1 d . . .
H10 H 0.3380 0.2991 0.6699 0.028 Uiso 1 1 calc R . .
C11 C 0.2257(3) 0.36170(19) 0.56273(12) 0.0239(5) Uani 1 1 d . . .
C12 C 0.2159(3) 0.4568(2) 0.50826(11) 0.0217(4) Uani 1 1 d . . .
H12 H 0.1417 0.4497 0.4595 0.026 Uiso 1 1 calc R . .
C13 C 0.3202(2) 0.56272(19) 0.52879(11) 0.0193(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.01558(11) 0.02665(12) 0.02175(12) 0.00031(9) 0.00200(8) -0.00128(8)
F9 0.0312(7) 0.0284(7) 0.0189(6) 0.0032(5) -0.0045(5) 0.0040(5)
F11 0.0410(8) 0.0250(7) 0.0402(8) -0.0051(6) 0.0070(6) -0.0109(6)
F13 0.0337(7) 0.0267(7) 0.0160(6) 0.0023(5) 0.0013(5) -0.0018(5)
N1 0.0154(8) 0.0201(9) 0.0163(8) -0.0004(7) 0.0016(6) -0.0007(7)
C1 0.0174(10) 0.0228(11) 0.0182(10) 0.0006(9) -0.0024(8) 0.0007(8)
C2 0.0325(13) 0.0261(12) 0.0369(13) -0.0031(10) -0.0058(10) 0.0101(10)
C3 0.0203(10) 0.0258(11) 0.0213(10) -0.0034(9) 0.0014(8) -0.0077(9)
C4 0.0419(14) 0.0375(14) 0.0279(12) -0.0010(11) 0.0075(10) -0.0211(11)
C5 0.0212(10) 0.0237(11) 0.0166(10) -0.0003(8) 0.0072(8) 0.0016(8)
C6 0.0261(11) 0.0322(12) 0.0169(10) 0.0010(9) 0.0019(8) 0.0021(9)
C7 0.0165(10) 0.0238(11) 0.0183(10) -0.0015(9) 0.0042(8) 0.0019(8)
C8 0.0149(9) 0.0211(10) 0.0189(10) -0.0011(8) 0.0053(8) 0.0028(8)
C9 0.0193(10) 0.0252(11) 0.0169(10) -0.0013(9) 0.0035(8) 0.0070(8)
C10 0.0264(11) 0.0206(11) 0.0249(11) 0.0016(9) 0.0102(9) 0.0042(9)
C11 0.0230(11) 0.0198(11) 0.0304(12) -0.0062(9) 0.0088(9) -0.0030(8)
C12 0.0192(10) 0.0261(11) 0.0197(10) -0.0058(9) 0.0029(8) 0.0012(8)
C13 0.0197(10) 0.0217(11) 0.0177(10) 0.0025(8) 0.0066(8) 0.0038(8)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F9 C9 1.355(2) . ?
F11 C11 1.358(2) . ?
F13 C13 1.356(2) . ?
N1 C1 1.520(2) . ?
N1 C3 1.524(2) . ?
N1 C7 1.526(2) . ?
N1 C5 1.527(2) . ?
C1 C2 1.513(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.517(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.518(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.503(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.385(3) . ?
C8 C13 1.395(3) . ?
C9 C10 1.375(3) . ?
C10 C11 1.378(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(3) . ?
C12 C13 1.378(3) . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C3 113.36(15) . . ?
C1 N1 C7 108.58(14) . . ?
C3 N1 C7 107.14(14) . . ?
C1 N1 C5 108.27(14) . . ?
C3 N1 C5 107.83(14) . . ?
C7 N1 C5 111.72(15) . . ?
C2 C1 N1 115.79(16) . . ?
C2 C1 H1A 108.3 . . ?
N1 C1 H1A 108.3 . . ?
C2 C1 H1B 108.3 . . ?
N1 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 N1 115.21(16) . . ?
C4 C3 H3A 108.5 . . ?
N1 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
N1 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N1 115.16(16) . . ?
C6 C5 H5A 108.5 . . ?
N1 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
N1 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N1 116.58(15) . . ?
C8 C7 H7A 108.1 . . ?
N1 C7 H7A 108.1 . . ?
C8 C7 H7B 108.1 . . ?
N1 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
C9 C8 C13 114.10(18) . . ?
C9 C8 C7 122.61(17) . . ?
C13 C8 C7 122.74(17) . . ?
F9 C9 C10 117.30(18) . . ?
F9 C9 C8 117.42(18) . . ?
C10 C9 C8 125.27(19) . . ?
C9 C10 C11 115.79(19) . . ?
C9 C10 H10 122.1 . . ?
C11 C10 H10 122.1 . . ?
F11 C11 C12 117.72(18) . . ?
F11 C11 C10 118.17(19) . . ?
C12 C11 C10 124.11(19) . . ?
C11 C12 C13 115.93(19) . . ?
C11 C12 H12 122.0 . . ?
C13 C12 H12 122.0 . . ?
F13 C13 C12 117.53(17) . . ?
F13 C13 C8 117.69(17) . . ?
C12 C13 C8 124.77(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 C2 -56.4(2) . . . . ?
C7 N1 C1 C2 -175.32(17) . . . . ?
C5 N1 C1 C2 63.2(2) . . . . ?
C1 N1 C3 C4 -48.0(2) . . . . ?
C7 N1 C3 C4 71.8(2) . . . . ?
C5 N1 C3 C4 -167.82(18) . . . . ?
C1 N1 C5 C6 -171.16(17) . . . . ?
C3 N1 C5 C6 -48.2(2) . . . . ?
C7 N1 C5 C6 69.3(2) . . . . ?
C1 N1 C7 C8 -55.0(2) . . . . ?
C3 N1 C7 C8 -177.78(16) . . . . ?
C5 N1 C7 C8 64.3(2) . . . . ?
N1 C7 C8 C9 -94.9(2) . . . . ?
N1 C7 C8 C13 94.1(2) . . . . ?
C13 C8 C9 F9 178.52(16) . . . . ?
C7 C8 C9 F9 6.8(3) . . . . ?
C13 C8 C9 C10 -0.5(3) . . . . ?
C7 C8 C9 C10 -172.29(18) . . . . ?
F9 C9 C10 C11 179.98(16) . . . . ?
C8 C9 C10 C11 -1.0(3) . . . . ?
C9 C10 C11 F11 -179.48(17) . . . . ?
C9 C10 C11 C12 1.5(3) . . . . ?
F11 C11 C12 C13 -179.47(17) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C11 C12 C13 F13 177.49(16) . . . . ?
C11 C12 C13 C8 -1.3(3) . . . . ?
C9 C8 C13 F13 -177.05(16) . . . . ?
C7 C8 C13 F13 -5.3(3) . . . . ?
C9 C8 C13 C12 1.7(3) . . . . ?
C7 C8 C13 C12 173.48(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.052

_iucr_refine_instructions_details 
;
TITL mm-239 in P 21/c
CELL   0.71073  12.9686   8.1122  14.4871  90.000 110.729  90.000
ZERR     4       0.0002   0.0002   0.0003   0.000   0.001   0.000
LATT  1
SYMM -X,1/2+Y,1/2-Z
SFAC        C       H       N       F       BR
UNIT        52      72       4      16       4
OMIT -3 50.5
OMIT 6 2 2
L.S.      10
TEMP  -150
SIZE  0.30 0.22 0.20
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.017500    1.266400
FVAR       0.62178
BR1   5    0.683828    0.004398    0.398617    11.00000    0.02240    0.03643 =
         0.01848    0.00620    0.00712    0.00703
F9    4    0.963834    0.576443    0.345363    11.00000    0.02255    0.01994 =
         0.02891   -0.00302    0.00623   -0.00372
F10   4    1.125283    0.429630    0.489803    11.00000    0.02309    0.04675 =
         0.02440   -0.00929   -0.00262   -0.00050
F12   4    0.980565   -0.089732    0.362505    11.00000    0.03996    0.02216 =
         0.04259    0.00726    0.02068    0.01134
F13   4    0.824909    0.057054    0.212251    11.00000    0.02417    0.02080 =
         0.03132   -0.00752    0.00944   -0.00325
N1    3    0.689491    0.434823    0.203307    11.00000    0.01452    0.01866 =
         0.01315    0.00182    0.00491   -0.00003
C1    1    0.707667    0.483440    0.309600    11.00000    0.01740    0.03349 =
         0.01233   -0.00059    0.00381    0.00358
AFIX  23
H1A   2    0.748878    0.393996    0.353817    11.00000   -1.20000
H1B   2    0.754256    0.583598    0.326090    11.00000   -1.20000
AFIX   0
C2    1    0.602870    0.516794    0.330345    11.00000    0.02222    0.04877 =
         0.02182   -0.00082    0.00914    0.00992
AFIX  33
H2A   2    0.621732    0.547285    0.399844    11.00000   -1.50000
H2B   2    0.556957    0.417392    0.316302    11.00000   -1.50000
H2C   2    0.562199    0.607258    0.288295    11.00000   -1.50000
AFIX   0
C3    1    0.620476    0.278634    0.179087    11.00000    0.01844    0.01942 =
         0.02390    0.00512    0.00824   -0.00210
AFIX  23
H3A   2    0.657989    0.193443    0.228495    11.00000   -1.20000
H3B   2    0.548559    0.301920    0.185872    11.00000   -1.20000
AFIX   0
C4    1    0.599270    0.208479    0.076834    11.00000    0.02467    0.02289 =
         0.02287   -0.00094   -0.00029   -0.00771
AFIX  33
H4A   2    0.554447    0.108410    0.067909    11.00000   -1.50000
H4B   2    0.669716    0.181590    0.069647    11.00000   -1.50000
H4C   2    0.559959    0.290159    0.026949    11.00000   -1.50000
AFIX   0
C5    1    0.628656    0.569614    0.130786    11.00000    0.01761    0.01892 =
         0.01577    0.00273    0.00196    0.00119
AFIX  23
H5A   2    0.630971    0.542163    0.064962    11.00000   -1.20000
H5B   2    0.550350    0.568954    0.125250    11.00000   -1.20000
AFIX   0
C6    1    0.673921    0.742808    0.157980    11.00000    0.02969    0.01776 =
         0.03068    0.00020    0.00663    0.00012
AFIX  33
H6A   2    0.629978    0.820651    0.107692    11.00000   -1.50000
H6B   2    0.750782    0.746376    0.161570    11.00000   -1.50000
H6C   2    0.670191    0.773067    0.222214    11.00000   -1.50000
AFIX   0
C7    1    0.800898    0.410486    0.191970    11.00000    0.01320    0.02098 =
         0.01620    0.00104    0.00638   -0.00093
AFIX  23
H7A   2    0.789346    0.348033    0.130402    11.00000   -1.20000
H7B   2    0.830602    0.520042    0.184412    11.00000   -1.20000
AFIX   0
C8    1    0.886031    0.321575    0.275943    11.00000    0.01388    0.02148 =
         0.01567    0.00075    0.00731    0.00104
C9    1    0.966024    0.410526    0.348621    11.00000    0.01737    0.01813 =
         0.01953   -0.00106    0.00818    0.00024
C10   1    1.048763    0.333490    0.423523    11.00000    0.01565    0.03515 =
         0.01622   -0.00732    0.00390   -0.00167
C11   1    1.055480    0.165163    0.431319    11.00000    0.02147    0.03791 =
         0.01838    0.00515    0.00822    0.01200
AFIX  43
H11   2    1.112013    0.112393    0.483681    11.00000   -1.20000
AFIX   0
C12   1    0.976765    0.076440    0.359986    11.00000    0.02562    0.01803 =
         0.02778    0.00352    0.01724    0.00623
C13   1    0.895178    0.151568    0.283192    11.00000    0.01729    0.02222 =
         0.01959   -0.00414    0.01012   -0.00118
HKLF   4
 
REM  mm-239 in P 21/c
REM R1 =  0.0242 for   2157 Fo > 4sig(Fo)  and  0.0322 for all   2573 data
REM    172 parameters refined using      0 restraints
 
END
 
WGHT      0.0175      1.2712
REM Highest difference peak  0.267,  deepest hole -0.287,  1-sigma level  0.053
Q1    1   0.5756  0.4183  0.3630  11.00000  0.05    0.27
Q2    1   0.5370  0.5347  0.2776  11.00000  0.05    0.26
Q3    1   0.8548  0.3587  0.2367  11.00000  0.05    0.24
Q4    1   0.6201  0.6049  0.3796  11.00000  0.05    0.23
Q5    1   0.6134  0.2866  0.0212  11.00000  0.05    0.23
Q6    1   0.9358  0.3573  0.2963  11.00000  0.05    0.21
Q7    1   0.6488  0.6516  0.1460  11.00000  0.05    0.21
Q8    1   0.7427  0.4051  0.1916  11.00000  0.05    0.19
Q9    1   0.6154  0.8260  0.0581  11.00000  0.05    0.19
Q10   1   0.6770  0.5142  0.1810  11.00000  0.05    0.19
Q11   1   0.9134  0.2510  0.2640  11.00000  0.05    0.19
Q12   1   0.8941  0.3524  0.3212  11.00000  0.05    0.18
Q13   1   0.9944  0.3695  0.3994  11.00000  0.05    0.18
Q14   1   0.6381  0.7822  0.1833  11.00000  0.05    0.18
Q15   1   0.8767  0.2409  0.2846  11.00000  0.05    0.18
Q16   1   0.6827  0.0955  0.0758  11.00000  0.05    0.17
Q17   1   1.1362  0.5795  0.4939  11.00000  0.05    0.17
Q18   1   1.0267  0.2636  0.4392  11.00000  0.05    0.17
Q19   1   0.7109  0.4639  0.2620  11.00000  0.05    0.17
Q20   1   0.8230  0.2722  0.4801  11.00000  0.05    0.16
Q21   1   0.6582  0.1265  0.3379  11.00000  0.05    0.16
Q22   1   0.6216  0.2557  0.1348  11.00000  0.05    0.16
Q23   1   0.9385  0.1246  0.3120  11.00000  0.05    0.15
Q24   1   0.9147 -0.1212  0.3256  11.00000  0.05    0.15
Q25   1   0.5820 -0.1038  0.3640  11.00000  0.05    0.15
;
_database_code_depnum_ccdc_archive 'CCDC 1005270'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-aa-85-5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 F3 N, Br'
_chemical_formula_sum            'C16 H17 Br F3 N'
_chemical_formula_weight         360.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pna21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   11.7838(2)
_cell_length_b                   20.3034(4)
_cell_length_c                   6.37720(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1525.75(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2204
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    2.718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6404
_exptl_absorpt_correction_T_max  0.7189
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18750
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2693
_reflns_number_gt                2494
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, et al., 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.7518P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.085(8)
_refine_ls_number_reflns         2693
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0235
_refine_ls_wR_factor_ref         0.0505
_refine_ls_wR_factor_gt          0.0491
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.866024(18) 0.232959(11) 0.19741(6) 0.02176(8) Uani 1 1 d . . .
F11 F 0.35013(13) 0.44311(7) 0.6476(3) 0.0328(5) Uani 1 1 d . . .
F12 F 0.45454(16) 0.46649(8) 0.2760(3) 0.0372(5) Uani 1 1 d . . .
F13 F 0.64225(13) 0.39862(7) 0.1701(4) 0.0331(4) Uani 1 1 d . . .
N1 N 0.5887(2) 0.20119(10) 0.7580(3) 0.0196(5) Uani 1 1 d . . .
C1 C 0.46409(17) 0.19818(10) 0.6972(6) 0.0172(4) Uani 1 1 d . . .
H1A H 0.4193 0.2214 0.8057 0.021 Uiso 1 1 calc R . .
H1B H 0.4539 0.2223 0.5636 0.021 Uiso 1 1 calc R . .
C2 C 0.4162(2) 0.12949(11) 0.6713(5) 0.0182(6) Uani 1 1 d . . .
C3 C 0.3556(2) 0.10091(14) 0.8337(5) 0.0225(6) Uani 1 1 d . . .
H3 H 0.3502 0.1229 0.9648 0.027 Uiso 1 1 calc R . .
C4 C 0.3027(3) 0.04025(14) 0.8064(5) 0.0286(7) Uani 1 1 d . . .
H4 H 0.2620 0.0207 0.9189 0.034 Uiso 1 1 calc R . .
C5 C 0.3095(3) 0.00858(14) 0.6150(5) 0.0319(8) Uani 1 1 d . . .
H5 H 0.2722 -0.0324 0.5952 0.038 Uiso 1 1 calc R . .
C6 C 0.3705(3) 0.03636(14) 0.4521(5) 0.0308(7) Uani 1 1 d . . .
H6 H 0.3767 0.0139 0.3220 0.037 Uiso 1 1 calc R . .
C7 C 0.4224(3) 0.09692(13) 0.4785(5) 0.0257(7) Uani 1 1 d . . .
H7 H 0.4624 0.1165 0.3652 0.031 Uiso 1 1 calc R . .
C8 C 0.6198(2) 0.27183(12) 0.8230(5) 0.0208(6) Uani 1 1 d . . .
H8A H 0.5870 0.2807 0.9631 0.025 Uiso 1 1 calc R . .
H8B H 0.7033 0.2750 0.8357 0.025 Uiso 1 1 calc R . .
C9 C 0.5794(2) 0.32410(11) 0.6737(6) 0.0181(6) Uani 1 1 d . . .
C10 C 0.4833(2) 0.36053(11) 0.7296(4) 0.0189(7) Uani 1 1 d . . .
H10 H 0.4459 0.3525 0.8591 0.023 Uiso 1 1 calc R . .
C11 C 0.4438(2) 0.40807(12) 0.5952(5) 0.0214(6) Uani 1 1 d . . .
C12 C 0.4961(2) 0.42109(13) 0.4076(5) 0.0243(6) Uani 1 1 d . . .
C13 C 0.5916(2) 0.38554(13) 0.3558(4) 0.0226(6) Uani 1 1 d . . .
C14 C 0.6357(2) 0.33764(13) 0.4853(4) 0.0203(6) Uani 1 1 d . . .
H14 H 0.7026 0.3144 0.4477 0.024 Uiso 1 1 calc R . .
C15 C 0.6622(3) 0.17850(15) 0.5825(5) 0.0317(7) Uani 1 1 d . . .
H15A H 0.6485 0.2060 0.4588 0.048 Uiso 1 1 calc R . .
H15B H 0.6445 0.1325 0.5492 0.048 Uiso 1 1 calc R . .
H15C H 0.7421 0.1820 0.6239 0.048 Uiso 1 1 calc R . .
C16 C 0.6103(3) 0.15877(14) 0.9471(5) 0.0284(7) Uani 1 1 d . . .
H16A H 0.5621 0.1735 1.0631 0.043 Uiso 1 1 calc R . .
H16B H 0.6902 0.1624 0.9880 0.043 Uiso 1 1 calc R . .
H16C H 0.5928 0.1128 0.9132 0.043 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02088(13) 0.02747(13) 0.01693(12) -0.00078(16) 0.00031(19) 0.00130(10)
F11 0.0250(8) 0.0244(8) 0.0489(16) 0.0077(8) 0.0057(8) 0.0081(6)
F12 0.0374(11) 0.0306(9) 0.0435(11) 0.0209(7) -0.0029(8) 0.0071(8)
F13 0.0383(9) 0.0342(8) 0.0269(12) 0.0104(9) 0.0098(9) -0.0008(7)
N1 0.0189(12) 0.0145(10) 0.0255(15) 0.0048(8) -0.0007(9) -0.0001(9)
C1 0.0153(11) 0.0163(10) 0.0201(11) 0.0005(16) 0.0016(17) 0.0013(8)
C2 0.0157(11) 0.0149(11) 0.0239(16) 0.0050(13) -0.0018(14) 0.0025(9)
C3 0.0240(16) 0.0239(15) 0.0196(16) -0.0006(11) 0.0024(12) 0.0025(12)
C4 0.0279(18) 0.0225(17) 0.0353(18) 0.0013(15) 0.0101(14) -0.0057(13)
C5 0.0303(17) 0.0169(15) 0.049(2) -0.0056(14) 0.0083(14) -0.0046(13)
C6 0.041(2) 0.0230(15) 0.0289(17) -0.0065(12) 0.0035(15) -0.0018(14)
C7 0.0312(19) 0.0208(15) 0.0252(16) 0.0008(12) 0.0028(14) -0.0014(13)
C8 0.0189(15) 0.0192(14) 0.0243(16) 0.0007(11) -0.0032(11) -0.0002(11)
C9 0.0170(12) 0.0125(10) 0.0248(15) 0.0030(13) -0.0064(14) -0.0037(9)
C10 0.0199(13) 0.0166(12) 0.0201(19) 0.0008(11) 0.0008(11) -0.0058(10)
C11 0.0164(15) 0.0159(13) 0.0319(15) 0.0004(12) -0.0007(12) 0.0013(11)
C12 0.0252(16) 0.0163(14) 0.0312(17) 0.0080(12) -0.0065(12) -0.0026(12)
C13 0.0266(16) 0.0220(14) 0.0194(15) 0.0040(11) 0.0016(13) -0.0072(12)
C14 0.0177(15) 0.0194(13) 0.0237(15) 0.0003(11) -0.0002(11) -0.0018(11)
C15 0.0282(18) 0.0232(16) 0.0438(19) -0.0023(14) 0.0130(15) 0.0031(13)
C16 0.0251(17) 0.0262(15) 0.0337(18) 0.0139(13) -0.0100(13) -0.0020(13)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F11 C11 1.355(3) . ?
F12 C12 1.339(3) . ?
F13 C13 1.353(3) . ?
N1 C15 1.488(4) . ?
N1 C16 1.503(3) . ?
N1 C1 1.520(3) . ?
N1 C8 1.537(3) . ?
C1 C2 1.513(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.385(4) . ?
C2 C7 1.398(4) . ?
C3 C4 1.392(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.503(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.399(4) . ?
C9 C14 1.400(4) . ?
C10 C11 1.372(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.372(4) . ?
C12 C13 1.377(4) . ?
C13 C14 1.377(4) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 N1 C16 109.1(2) . . ?
C15 N1 C1 111.0(2) . . ?
C16 N1 C1 110.2(2) . . ?
C15 N1 C8 110.7(2) . . ?
C16 N1 C8 106.1(2) . . ?
C1 N1 C8 109.64(18) . . ?
C2 C1 N1 115.16(18) . . ?
C2 C1 H1A 108.5 . . ?
N1 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
N1 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C3 C2 C7 119.1(2) . . ?
C3 C2 C1 119.8(3) . . ?
C7 C2 C1 120.8(3) . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 120.3(3) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
C9 C8 N1 114.4(2) . . ?
C9 C8 H8A 108.7 . . ?
N1 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
N1 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C14 119.9(3) . . ?
C10 C9 C8 117.9(3) . . ?
C14 C9 C8 122.2(2) . . ?
C11 C10 C9 119.2(3) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
F11 C11 C12 118.7(2) . . ?
F11 C11 C10 119.5(2) . . ?
C12 C11 C10 121.9(2) . . ?
F12 C12 C11 121.0(3) . . ?
F12 C12 C13 120.6(3) . . ?
C11 C12 C13 118.4(2) . . ?
F13 C13 C12 117.9(2) . . ?
F13 C13 C14 119.8(3) . . ?
C12 C13 C14 122.3(3) . . ?
C13 C14 C9 118.3(3) . . ?
C13 C14 H14 120.9 . . ?
C9 C14 H14 120.9 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N1 C1 C2 69.0(3) . . . . ?
C16 N1 C1 C2 -51.9(4) . . . . ?
C8 N1 C1 C2 -168.4(3) . . . . ?
N1 C1 C2 C3 98.2(3) . . . . ?
N1 C1 C2 C7 -88.2(4) . . . . ?
C7 C2 C3 C4 0.7(4) . . . . ?
C1 C2 C3 C4 174.4(3) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
C4 C5 C6 C7 -1.8(5) . . . . ?
C5 C6 C7 C2 1.8(5) . . . . ?
C3 C2 C7 C6 -1.3(4) . . . . ?
C1 C2 C7 C6 -174.9(3) . . . . ?
C15 N1 C8 C9 75.1(3) . . . . ?
C16 N1 C8 C9 -166.7(2) . . . . ?
C1 N1 C8 C9 -47.7(3) . . . . ?
N1 C8 C9 C10 102.7(3) . . . . ?
N1 C8 C9 C14 -78.4(3) . . . . ?
C14 C9 C10 C11 1.8(4) . . . . ?
C8 C9 C10 C11 -179.3(2) . . . . ?
C9 C10 C11 F11 179.4(2) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
F11 C11 C12 F12 -1.4(4) . . . . ?
C10 C11 C12 F12 178.2(2) . . . . ?
F11 C11 C12 C13 179.7(2) . . . . ?
C10 C11 C12 C13 -0.7(4) . . . . ?
F12 C12 C13 F13 0.8(4) . . . . ?
C11 C12 C13 F13 179.8(2) . . . . ?
F12 C12 C13 C14 -178.8(2) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
F13 C13 C14 C9 -178.3(2) . . . . ?
C12 C13 C14 C9 1.4(4) . . . . ?
C10 C9 C14 C13 -2.3(4) . . . . ?
C8 C9 C14 C13 178.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.045

_iucr_refine_instructions_details 
;
TITL mm-aa-85-5 in P n a 21
REM  transformed from space group : P 21 n b
CELL   0.71073 11.7838 20.3034  6.3772   90.000   90.000   90.000
ZERR   4        0.0002  0.0004  0.0001    0.000    0.000    0.000
LATT   -1
SYMM   -X,-Y,1/2+Z
SYMM   1/2-X,1/2+Y,1/2+Z
SYMM   1/2+X,1/2-Y,+Z
SFAC        C       H       N       F       BR
UNIT        64      68       4      12       4
OMIT -3 50.5
OMIT 0 6 1
L.S.      10
TEMP  -150
SIZE  0.18 0.16 0.13
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.000000    0.751800
FVAR       0.45008
BR1   5    0.866024    0.232959    0.197414    11.00000    0.02088    0.02747 =
         0.01693   -0.00078    0.00031    0.00130
F11   4    0.350126    0.443108    0.647620    11.00000    0.02498    0.02437 =
         0.04893    0.00770    0.00566    0.00814
F12   4    0.454542    0.466492    0.275975    11.00000    0.03740    0.03063 =
         0.04347    0.02087   -0.00291    0.00713
F13   4    0.642250    0.398620    0.170107    11.00000    0.03832    0.03418 =
         0.02686    0.01044    0.00978   -0.00076
N1    3    0.588744    0.201189    0.757984    11.00000    0.01890    0.01452 =
         0.02547    0.00478   -0.00071   -0.00011
C1    1    0.464089    0.198181    0.697176    11.00000    0.01530    0.01626 =
         0.02013    0.00046    0.00158    0.00134
AFIX  23
H1A   2    0.419347    0.221440    0.805717    11.00000   -1.20000
H1B   2    0.453874    0.222313    0.563609    11.00000   -1.20000
AFIX   0
C2    1    0.416185    0.129494    0.671338    11.00000    0.01568    0.01488 =
         0.02394    0.00496   -0.00184    0.00250
C3    1    0.355648    0.100909    0.833706    11.00000    0.02395    0.02387 =
         0.01964   -0.00063    0.00236    0.00249
AFIX  43
H3    2    0.350219    0.122891    0.964826    11.00000   -1.20000
AFIX   0
C4    1    0.302707    0.040249    0.806363    11.00000    0.02794    0.02246 =
         0.03533    0.00132    0.01006   -0.00571
AFIX  43
H4    2    0.262031    0.020675    0.918874    11.00000   -1.20000
AFIX   0
C5    1    0.309516    0.008585    0.614951    11.00000    0.03028    0.01694 =
         0.04851   -0.00559    0.00835   -0.00457
AFIX  43
H5    2    0.272187   -0.032420    0.595174    11.00000   -1.20000
AFIX   0
C6    1    0.370470    0.036362    0.452051    11.00000    0.04054    0.02300 =
         0.02888   -0.00646    0.00351   -0.00183
AFIX  43
H6    2    0.376709    0.013855    0.321959    11.00000   -1.20000
AFIX   0
C7    1    0.422350    0.096919    0.478547    11.00000    0.03120    0.02076 =
         0.02524    0.00081    0.00281   -0.00144
AFIX  43
H7    2    0.462362    0.116461    0.365170    11.00000   -1.20000
AFIX   0
C8    1    0.619787    0.271833    0.822995    11.00000    0.01890    0.01916 =
         0.02429    0.00065   -0.00318   -0.00023
AFIX  23
H8A   2    0.587012    0.280690    0.963126    11.00000   -1.20000
H8B   2    0.703338    0.275045    0.835651    11.00000   -1.20000
AFIX   0
C9    1    0.579388    0.324097    0.673658    11.00000    0.01695    0.01248 =
         0.02482    0.00302   -0.00644   -0.00372
C10   1    0.483328    0.360533    0.729639    11.00000    0.01992    0.01663 =
         0.02014    0.00079    0.00080   -0.00578
AFIX  43
H10   2    0.445920    0.352477    0.859083    11.00000   -1.20000
AFIX   0
C11   1    0.443789    0.408066    0.595238    11.00000    0.01637    0.01589 =
         0.03191    0.00041   -0.00068    0.00130
C12   1    0.496088    0.421090    0.407600    11.00000    0.02520    0.01634 =
         0.03122    0.00796   -0.00652   -0.00264
C13   1    0.591584    0.385541    0.355847    11.00000    0.02657    0.02195 =
         0.01936    0.00405    0.00159   -0.00724
C14   1    0.635706    0.337642    0.485287    11.00000    0.01774    0.01938 =
         0.02369    0.00033   -0.00019   -0.00185
AFIX  43
H14   2    0.702645    0.314397    0.447668    11.00000   -1.20000
AFIX   0
C15   1    0.662231    0.178500    0.582476    11.00000    0.02822    0.02319 =
         0.04381   -0.00230    0.01299    0.00305
AFIX  33
H15A  2    0.648538    0.206003    0.458751    11.00000   -1.50000
H15B  2    0.644459    0.132520    0.549211    11.00000   -1.50000
H15C  2    0.742086    0.182038    0.623894    11.00000   -1.50000
AFIX   0
C16   1    0.610340    0.158770    0.947051    11.00000    0.02509    0.02625 =
         0.03372    0.01390   -0.01001   -0.00198
AFIX  33
H16A  2    0.562070    0.173450    1.063134    11.00000   -1.50000
H16B  2    0.690249    0.162407    0.988030    11.00000   -1.50000
H16C  2    0.592780    0.112802    0.913232    11.00000   -1.50000
HKLF   4
 
REM  mm-aa-85-5 in P n a 21
REM R1 =  0.0235 for   2494 Fo > 4sig(Fo)  and  0.0274 for all   2693 data
REM    190 parameters refined using      1 restraints
 
END
 
WGHT      0.0000      0.7583
REM Highest difference peak  0.198,  deepest hole -0.192,  1-sigma level  0.045
Q1    1   0.5813  0.2808  0.6957  11.00000  0.05    0.20
Q2    1   0.9037  0.2389  0.0132  11.00000  0.05    0.19
Q3    1   0.6350  0.1889  0.6965  11.00000  0.05    0.19
Q4    1   0.7634  0.2985  0.1949  11.00000  0.05    0.18
Q5    1   0.5259  0.3314  0.6821  11.00000  0.05    0.18
Q6    1   0.4839  0.3997  0.6961  11.00000  0.05    0.17
Q7    1   0.4518  0.1063  0.6204  11.00000  0.05    0.17
Q8    1   0.6012  0.2301  0.6151  11.00000  0.05    0.17
Q9    1   0.4132  0.1628  0.6560  11.00000  0.05    0.17
Q10   1   0.6376  0.3802  0.4999  11.00000  0.05    0.17
Q11   1   0.8622  0.3028  0.1991  11.00000  0.05    0.16
Q12   1   0.5346  0.1984  0.7223  11.00000  0.05    0.16
Q13   1   0.4943  0.4286  0.5622  11.00000  0.05    0.16
Q14   1   0.3630  0.1196  1.1899  11.00000  0.05    0.16
Q15   1   0.7613  0.2220  0.9150  11.00000  0.05    0.16
Q16   1   0.3740  0.2023  0.4487  11.00000  0.05    0.16
Q17   1   0.4989  0.3973  1.0601  11.00000  0.05    0.15
Q18   1   0.3618  0.1212  0.7220  11.00000  0.05    0.14
Q19   1   0.4179  0.4210  0.6078  11.00000  0.05    0.14
Q20   1   0.3481  0.1101  0.8875  11.00000  0.05    0.14
Q21   1   0.7011  0.2549  0.9093  11.00000  0.05    0.14
Q22   1   0.6637  0.3368  0.8320  11.00000  0.05    0.14
Q23   1   0.7016  0.2493  0.4723  11.00000  0.05    0.14
Q24   1   0.4366  0.1089  0.7671  11.00000  0.05    0.14
Q25   1   0.3594  0.0688  0.8391  11.00000  0.05    0.14
;
_database_code_depnum_ccdc_archive 'CCDC 1005271'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-200

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 F4 N, Br'
_chemical_formula_sum            'C16 H16 Br F4 N'
_chemical_formula_weight         378.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.0793(2)
_cell_length_b                   16.9865(3)
_cell_length_c                   11.3472(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.1410(10)
_cell_angle_gamma                90.00
_cell_volume                     1554.94(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3888
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    2.680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4136
_exptl_absorpt_correction_T_max  0.8557
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9119
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2750
_reflns_number_gt                2262
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, et al., 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0235P)²+0.0496P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2750
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0625
_refine_ls_wR_factor_gt          0.0601
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.47246(3) 0.231881(13) 0.62571(2) 0.02379(9) Uani 1 1 d . . .
F10 F 0.59548(17) 0.42967(7) 0.44898(11) 0.0273(3) Uani 1 1 d . . .
F11 F 0.69926(17) 0.57543(7) 0.40631(13) 0.0311(3) Uani 1 1 d . . .
F13 F 0.38725(17) 0.57596(7) 0.04286(11) 0.0274(3) Uani 1 1 d . . .
F14 F 0.28882(16) 0.42872(7) 0.08251(11) 0.0242(3) Uani 1 1 d . . .
N1 N 0.4552(2) 0.27300(10) 0.26272(16) 0.0182(4) Uani 1 1 d . . .
C1 C 0.3505(3) 0.20345(13) 0.3027(2) 0.0195(5) Uani 1 1 d . . .
H1A H 0.3416 0.2071 0.3892 0.023 Uiso 1 1 calc R . .
H1B H 0.2372 0.2087 0.2656 0.023 Uiso 1 1 calc R . .
C2 C 0.4151(3) 0.12351(13) 0.2741(2) 0.0189(5) Uani 1 1 d . . .
C3 C 0.5121(3) 0.08135(13) 0.3580(2) 0.0221(5) Uani 1 1 d . . .
H3 H 0.5451 0.1052 0.4313 0.026 Uiso 1 1 calc R . .
C4 C 0.5603(3) 0.00479(14) 0.3346(2) 0.0251(6) Uani 1 1 d . . .
H4 H 0.6263 -0.0236 0.3919 0.030 Uiso 1 1 calc R . .
C5 C 0.5126(3) -0.03017(14) 0.2283(2) 0.0262(6) Uani 1 1 d . . .
H5 H 0.5461 -0.0826 0.2126 0.031 Uiso 1 1 calc R . .
C6 C 0.4159(3) 0.01099(14) 0.1444(2) 0.0266(6) Uani 1 1 d . . .
H6 H 0.3834 -0.0132 0.0712 0.032 Uiso 1 1 calc R . .
C7 C 0.3667(3) 0.08743(13) 0.1674(2) 0.0228(5) Uani 1 1 d . . .
H7 H 0.2997 0.1154 0.1101 0.027 Uiso 1 1 calc R . .
C8 C 0.3627(3) 0.34631(12) 0.2981(2) 0.0195(5) Uani 1 1 d . . .
H8A H 0.2494 0.3442 0.2603 0.023 Uiso 1 1 calc R . .
H8B H 0.3520 0.3449 0.3845 0.023 Uiso 1 1 calc R . .
C9 C 0.4394(3) 0.42394(13) 0.2670(2) 0.0182(5) Uani 1 1 d . . .
C10 C 0.5447(3) 0.46456(14) 0.3462(2) 0.0210(5) Uani 1 1 d . . .
C11 C 0.5968(3) 0.53986(14) 0.3253(2) 0.0219(5) Uani 1 1 d . . .
C12 C 0.5454(3) 0.57903(13) 0.2239(2) 0.0219(5) Uani 1 1 d . . .
H12 H 0.5798 0.6315 0.2100 0.026 Uiso 1 1 calc R . .
C13 C 0.4425(3) 0.53966(14) 0.1433(2) 0.0210(5) Uani 1 1 d . . .
C14 C 0.3904(3) 0.46381(13) 0.1638(2) 0.0198(5) Uani 1 1 d . . .
C15 C 0.4697(3) 0.27111(13) 0.1313(2) 0.0244(6) Uani 1 1 d . . .
H15A H 0.3587 0.2728 0.0919 0.037 Uiso 1 1 calc R . .
H15B H 0.5259 0.2226 0.1093 0.037 Uiso 1 1 calc R . .
H15C H 0.5338 0.3167 0.1070 0.037 Uiso 1 1 calc R . .
C16 C 0.6258(3) 0.27010(13) 0.3221(2) 0.0230(5) Uani 1 1 d . . .
H16A H 0.6174 0.2712 0.4079 0.035 Uiso 1 1 calc R . .
H16B H 0.6899 0.3157 0.2976 0.035 Uiso 1 1 calc R . .
H16C H 0.6815 0.2216 0.2995 0.035 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02380(15) 0.02362(14) 0.02391(14) -0.00198(11) 0.00081(10) 0.00128(11)
F10 0.0304(8) 0.0293(8) 0.0216(7) 0.0004(6) -0.0057(6) 0.0027(6)
F11 0.0265(8) 0.0276(8) 0.0381(9) -0.0086(6) -0.0075(7) -0.0014(6)
F13 0.0334(9) 0.0257(8) 0.0233(8) 0.0066(6) 0.0029(6) 0.0016(6)
F14 0.0260(8) 0.0241(7) 0.0218(7) -0.0011(6) -0.0040(6) -0.0014(6)
N1 0.0164(10) 0.0172(10) 0.0213(10) 0.0039(8) 0.0043(8) 0.0003(8)
C1 0.0157(12) 0.0205(12) 0.0225(13) 0.0032(10) 0.0028(10) -0.0011(10)
C2 0.0178(13) 0.0197(12) 0.0197(12) 0.0036(10) 0.0042(10) -0.0034(10)
C3 0.0226(13) 0.0221(12) 0.0215(13) 0.0030(10) 0.0013(11) -0.0034(10)
C4 0.0177(13) 0.0233(13) 0.0344(15) 0.0059(11) 0.0025(11) 0.0010(10)
C5 0.0249(14) 0.0192(12) 0.0356(15) -0.0010(11) 0.0113(12) -0.0034(10)
C6 0.0274(14) 0.0278(14) 0.0249(14) -0.0049(11) 0.0056(11) -0.0100(11)
C7 0.0224(13) 0.0233(13) 0.0227(13) 0.0033(10) -0.0004(11) -0.0048(10)
C8 0.0188(13) 0.0199(12) 0.0202(12) -0.0007(10) 0.0030(10) 0.0026(10)
C9 0.0171(12) 0.0181(12) 0.0198(12) -0.0009(10) 0.0039(10) 0.0028(9)
C10 0.0198(13) 0.0243(13) 0.0187(13) -0.0003(10) 0.0006(10) 0.0050(10)
C11 0.0150(13) 0.0220(13) 0.0288(14) -0.0073(11) 0.0013(11) 0.0013(10)
C12 0.0173(13) 0.0188(12) 0.0304(14) 0.0006(10) 0.0079(11) -0.0010(10)
C13 0.0195(13) 0.0227(13) 0.0215(13) 0.0025(10) 0.0066(10) 0.0056(10)
C14 0.0166(12) 0.0223(13) 0.0205(13) -0.0031(10) 0.0009(10) 0.0022(10)
C15 0.0331(15) 0.0209(13) 0.0198(12) -0.0004(11) 0.0062(11) -0.0014(11)
C16 0.0166(13) 0.0214(12) 0.0311(14) 0.0002(11) 0.0010(11) -0.0007(10)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F10 C10 1.351(3) . ?
F11 C11 1.347(3) . ?
F13 C13 1.350(3) . ?
F14 C14 1.340(3) . ?
N1 C16 1.502(3) . ?
N1 C15 1.503(3) . ?
N1 C8 1.517(3) . ?
N1 C1 1.536(3) . ?
C1 C2 1.497(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C7 1.394(3) . ?
C2 C3 1.397(3) . ?
C3 C4 1.387(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.507(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.387(3) . ?
C9 C14 1.391(3) . ?
C10 C11 1.371(3) . ?
C11 C12 1.373(3) . ?
C12 C13 1.376(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N1 C15 108.95(18) . . ?
C16 N1 C8 111.19(17) . . ?
C15 N1 C8 110.25(17) . . ?
C16 N1 C1 110.44(16) . . ?
C15 N1 C1 110.53(17) . . ?
C8 N1 C1 105.45(16) . . ?
C2 C1 N1 115.47(18) . . ?
C2 C1 H1A 108.4 . . ?
N1 C1 H1A 108.4 . . ?
C2 C1 H1B 108.4 . . ?
N1 C1 H1B 108.4 . . ?
H1A C1 H1B 107.5 . . ?
C7 C2 C3 119.1(2) . . ?
C7 C2 C1 120.2(2) . . ?
C3 C2 C1 120.5(2) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
C9 C8 N1 116.22(18) . . ?
C9 C8 H8A 108.2 . . ?
N1 C8 H8A 108.2 . . ?
C9 C8 H8B 108.2 . . ?
N1 C8 H8B 108.2 . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 C14 116.1(2) . . ?
C10 C9 C8 121.9(2) . . ?
C14 C9 C8 121.4(2) . . ?
F10 C10 C11 118.5(2) . . ?
F10 C10 C9 119.2(2) . . ?
C11 C10 C9 122.3(2) . . ?
F11 C11 C10 118.9(2) . . ?
F11 C11 C12 120.1(2) . . ?
C10 C11 C12 121.1(2) . . ?
C11 C12 C13 117.7(2) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
F13 C13 C12 120.0(2) . . ?
F13 C13 C14 118.6(2) . . ?
C12 C13 C14 121.4(2) . . ?
F14 C14 C13 118.7(2) . . ?
F14 C14 C9 119.8(2) . . ?
C13 C14 C9 121.4(2) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N1 C1 C2 -61.4(2) . . . . ?
C15 N1 C1 C2 59.3(2) . . . . ?
C8 N1 C1 C2 178.42(19) . . . . ?
N1 C1 C2 C7 -89.9(3) . . . . ?
N1 C1 C2 C3 95.9(2) . . . . ?
C7 C2 C3 C4 0.5(3) . . . . ?
C1 C2 C3 C4 174.7(2) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C5 C6 C7 C2 0.5(4) . . . . ?
C3 C2 C7 C6 -0.7(3) . . . . ?
C1 C2 C7 C6 -175.0(2) . . . . ?
C16 N1 C8 C9 61.0(2) . . . . ?
C15 N1 C8 C9 -59.9(2) . . . . ?
C1 N1 C8 C9 -179.24(18) . . . . ?
N1 C8 C9 C10 -94.0(3) . . . . ?
N1 C8 C9 C14 95.1(3) . . . . ?
C14 C9 C10 F10 179.22(19) . . . . ?
C8 C9 C10 F10 7.8(3) . . . . ?
C14 C9 C10 C11 0.6(3) . . . . ?
C8 C9 C10 C11 -170.8(2) . . . . ?
F10 C10 C11 F11 1.5(3) . . . . ?
C9 C10 C11 F11 -179.9(2) . . . . ?
F10 C10 C11 C12 -178.2(2) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
F11 C11 C12 C13 179.15(19) . . . . ?
C10 C11 C12 C13 -1.2(3) . . . . ?
C11 C12 C13 F13 179.3(2) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
F13 C13 C14 F14 0.9(3) . . . . ?
C12 C13 C14 F14 179.3(2) . . . . ?
F13 C13 C14 C9 -178.26(19) . . . . ?
C12 C13 C14 C9 0.2(3) . . . . ?
C10 C9 C14 F14 179.96(19) . . . . ?
C8 C9 C14 F14 -8.6(3) . . . . ?
C10 C9 C14 C13 -0.9(3) . . . . ?
C8 C9 C14 C13 170.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.068

_iucr_refine_instructions_details 
;
TITL mm-200 in P 21/n
CELL   0.71073   8.0793  16.9865  11.3472  90.000  93.141  90.000
ZERR     4       0.0002   0.0003   0.0002   0.000   0.001   0.000
LATT  1
SYMM 1/2-X,1/2+Y,1/2-Z
SFAC        C       H       N       F       BR
UNIT        64      64       4      16       4
L.S.      10
OMIT -3 50.05
OMIT 0 2 6
TEMP  -150
SIZE  0.40 0.19 0.06
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.023500    0.049600
FVAR       0.37097
BR1   5    0.472457    0.231881    0.625712    11.00000    0.02380    0.02362 =
         0.02391   -0.00198    0.00081    0.00128
F10   4    0.595480    0.429667    0.448977    11.00000    0.03036    0.02927 =
         0.02157    0.00037   -0.00573    0.00269
F11   4    0.699264    0.575430    0.406314    11.00000    0.02650    0.02762 =
         0.03806   -0.00855   -0.00751   -0.00140
F13   4    0.387250    0.575959    0.042862    11.00000    0.03335    0.02572 =
         0.02330    0.00665    0.00291    0.00163
F14   4    0.288820    0.428719    0.082510    11.00000    0.02602    0.02405 =
         0.02181   -0.00111   -0.00400   -0.00136
N1    3    0.455161    0.273001    0.262717    11.00000    0.01637    0.01723 =
         0.02134    0.00391    0.00429    0.00033
C1    1    0.350487    0.203449    0.302669    11.00000    0.01573    0.02051 =
         0.02252    0.00320    0.00283   -0.00114
AFIX  23
H1A   2    0.341629    0.207068    0.389173    11.00000   -1.20000
H1B   2    0.237224    0.208750    0.265616    11.00000   -1.20000
AFIX   0
C2    1    0.415077    0.123505    0.274141    11.00000    0.01777    0.01966 =
         0.01972    0.00364    0.00419   -0.00342
C3    1    0.512060    0.081352    0.357995    11.00000    0.02255    0.02211 =
         0.02154    0.00300    0.00129   -0.00342
AFIX  43
H3    2    0.545117    0.105171    0.431295    11.00000   -1.20000
AFIX   0
C4    1    0.560280    0.004791    0.334578    11.00000    0.01771    0.02334 =
         0.03444    0.00591    0.00248    0.00099
AFIX  43
H4    2    0.626328   -0.023639    0.391864    11.00000   -1.20000
AFIX   0
C5    1    0.512593   -0.030170    0.228347    11.00000    0.02492    0.01922 =
         0.03565   -0.00099    0.01126   -0.00336
AFIX  43
H5    2    0.546068   -0.082571    0.212638    11.00000   -1.20000
AFIX   0
C6    1    0.415863    0.010986    0.144363    11.00000    0.02745    0.02780 =
         0.02490   -0.00487    0.00555   -0.01005
AFIX  43
H6    2    0.383365   -0.013169    0.071207    11.00000   -1.20000
AFIX   0
C7    1    0.366709    0.087432    0.167388    11.00000    0.02236    0.02331 =
         0.02267    0.00330   -0.00035   -0.00480
AFIX  43
H7    2    0.299701    0.115373    0.110090    11.00000   -1.20000
AFIX   0
C8    1    0.362724    0.346306    0.298060    11.00000    0.01877    0.01986 =
         0.02017   -0.00073    0.00302    0.00257
AFIX  23
H8A   2    0.249385    0.344185    0.260334    11.00000   -1.20000
H8B   2    0.351994    0.344871    0.384527    11.00000   -1.20000
AFIX   0
C9    1    0.439364    0.423941    0.266987    11.00000    0.01715    0.01805 =
         0.01985   -0.00089    0.00386    0.00281
C10   1    0.544671    0.464558    0.346238    11.00000    0.01985    0.02429 =
         0.01868   -0.00032    0.00057    0.00502
C11   1    0.596755    0.539861    0.325252    11.00000    0.01496    0.02204 =
         0.02882   -0.00730    0.00131    0.00130
C12   1    0.545406    0.579031    0.223944    11.00000    0.01726    0.01875 =
         0.03042    0.00061    0.00793   -0.00104
AFIX  43
H12   2    0.579756    0.631542    0.209994    11.00000   -1.20000
AFIX   0
C13   1    0.442512    0.539662    0.143305    11.00000    0.01953    0.02270 =
         0.02145    0.00253    0.00664    0.00556
C14   1    0.390444    0.463809    0.163765    11.00000    0.01663    0.02228 =
         0.02047   -0.00313    0.00085    0.00219
C15   1    0.469668    0.271114    0.131287    11.00000    0.03312    0.02086 =
         0.01985   -0.00043    0.00616   -0.00138
AFIX  33
H15A  2    0.358730    0.272803    0.091859    11.00000   -1.50000
H15B  2    0.525886    0.222594    0.109275    11.00000   -1.50000
H15C  2    0.533850    0.316715    0.107013    11.00000   -1.50000
AFIX   0
C16   1    0.625815    0.270100    0.322067    11.00000    0.01657    0.02145 =
         0.03106    0.00025    0.00103   -0.00065
AFIX  33
H16A  2    0.617443    0.271184    0.407885    11.00000   -1.50000
H16B  2    0.689913    0.315669    0.297569    11.00000   -1.50000
H16C  2    0.681454    0.221555    0.299477    11.00000   -1.50000
HKLF   4
 
REM  mm-200 in P 21/n
REM R1 =  0.0270 for   2262 Fo > 4sig(Fo)  and  0.0378 for all   2750 data
REM    199 parameters refined using      0 restraints
 
END
 
WGHT      0.0235      0.0496
REM Highest difference peak  0.280,  deepest hole -0.306,  1-sigma level  0.068
Q1    1   0.4151  0.2361  0.2829  11.00000  0.05    0.28
Q2    1   0.6945  0.4604  0.2473  11.00000  0.05    0.28
Q3    1   0.4709  0.3016  0.6273  11.00000  0.05    0.27
Q4    1   0.3986  0.1578  0.2873  11.00000  0.05    0.25
Q5    1   0.6583 -0.0263  0.1462  11.00000  0.05    0.25
Q6    1   0.7287  0.2346  0.1617  11.00000  0.05    0.25
Q7    1   0.3442  0.1031  0.2381  11.00000  0.05    0.24
Q8    1   0.5902  0.2327  0.1248  11.00000  0.05    0.23
Q9    1   0.2699  0.2211  0.2556  11.00000  0.05    0.23
Q10   1   0.3576  0.0464  0.1780  11.00000  0.05    0.23
Q11   1   0.8401  0.3583  0.3439  11.00000  0.05    0.21
Q12   1   0.3209 -0.0584  0.2219  11.00000  0.05    0.21
Q13   1   0.8026  0.5824  0.2654  11.00000  0.05    0.21
Q14   1   0.5571  0.5613  0.2831  11.00000  0.05    0.21
Q15   1   0.6356  0.2400  0.5466  11.00000  0.05    0.20
Q16   1   0.6421  0.6534  0.1611  11.00000  0.05    0.20
Q17   1   0.3160  0.2361  0.7115  11.00000  0.05    0.20
Q18   1   0.2535  0.2778  0.0659  11.00000  0.05    0.20
Q19   1   0.6065  0.4996  0.3223  11.00000  0.05    0.19
Q20   1   0.2952  0.5229  0.2066  11.00000  0.05    0.19
Q21   1   0.6071  0.1653  0.0382  11.00000  0.05    0.19
Q22   1   0.3467  0.1007  0.4067  11.00000  0.05    0.19
Q23   1   0.4792  0.1183  0.0595  11.00000  0.05    0.19
Q24   1   0.7271  0.2631  0.0902  11.00000  0.05    0.19
Q25   1   0.6618 -0.0941  0.0809  11.00000  0.05    0.18
;
_database_code_depnum_ccdc_archive 'CCDC 1005272'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-md-09-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 F5 N2, Br'
_chemical_formula_sum            'C12 H8 Br F5 N2'
_chemical_formula_weight         355.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   P31

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   8.72990(10)
_cell_length_b                   8.72990(10)
_cell_length_c                   14.3094(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     944.43(3)
_cell_formula_units_Z            3
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1563
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.42
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.873
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             522
_exptl_absorpt_coefficient_mu    3.316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2879
_exptl_absorpt_correction_T_max  0.3364
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5427
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.92
_diffrn_reflns_theta_max         25.21
_reflns_number_total             2170
_reflns_number_gt                2116
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, et al., 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0056P)²+0.1103P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.035(6)
_refine_ls_number_reflns         2170
_refine_ls_number_parameters     187
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0199
_refine_ls_R_factor_gt           0.0189
_refine_ls_wR_factor_ref         0.0384
_refine_ls_wR_factor_gt          0.0381
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.18488(3) 0.69282(3) 0.477996(19) 0.02014(7) Uani 1 1 d . . .
F8 F -0.04575(19) -0.0397(2) 0.52823(10) 0.0292(4) Uani 1 1 d . . .
F9 F -0.0254(2) -0.2159(2) 0.67781(13) 0.0324(4) Uani 1 1 d . . .
F10 F 0.2766(2) -0.0744(2) 0.78069(9) 0.0305(4) Uani 1 1 d . . .
F11 F 0.54972(19) 0.2502(2) 0.73799(10) 0.0311(4) Uani 1 1 d . . .
F12 F 0.5289(2) 0.4281(2) 0.58957(11) 0.0314(4) Uani 1 1 d . . .
N1 N 0.2993(3) 0.2598(3) 0.38222(13) 0.0173(4) Uani 1 1 d . . .
N2 N 0.3113(3) 0.5093(3) 0.3140(3) 0.0229(4) Uani 1 1 d D . .
H2A H 0.283(4) 0.542(3) 0.3687(15) 0.027 Uiso 1 1 d D . .
H2B H 0.340(4) 0.585(3) 0.2660(15) 0.027 Uiso 1 1 d D . .
C1 C 0.3393(3) 0.3741(3) 0.30875(16) 0.0185(5) Uani 1 1 d . . .
C2 C 0.4122(3) 0.3420(3) 0.22756(17) 0.0222(6) Uani 1 1 d . . .
H2 H 0.4433 0.4201 0.1758 0.027 Uiso 1 1 calc R . .
C3 C 0.4382(3) 0.2017(3) 0.22280(17) 0.0247(6) Uani 1 1 d . . .
H3 H 0.4887 0.1828 0.1683 0.030 Uiso 1 1 calc R . .
C4 C 0.3902(4) 0.0830(4) 0.29909(18) 0.0240(7) Uani 1 1 d . . .
H4 H 0.4061 -0.0168 0.2961 0.029 Uiso 1 1 calc R . .
C5 C 0.3213(3) 0.1150(3) 0.37620(17) 0.0205(5) Uani 1 1 d . . .
H5 H 0.2872 0.0354 0.4275 0.025 Uiso 1 1 calc R . .
C6 C 0.2303(3) 0.2969(3) 0.46978(17) 0.0230(6) Uani 1 1 d . . .
H6A H 0.1054 0.2644 0.4600 0.028 Uiso 1 1 calc R . .
H6B H 0.2986 0.4255 0.4828 0.028 Uiso 1 1 calc R . .
C7 C 0.2413(3) 0.1984(3) 0.55315(17) 0.0179(5) Uani 1 1 d . . .
C8 C 0.1034(3) 0.0343(3) 0.57901(17) 0.0194(5) Uani 1 1 d . . .
C9 C 0.1114(4) -0.0575(3) 0.65517(17) 0.0197(6) Uani 1 1 d . . .
C10 C 0.2637(3) 0.0153(4) 0.70748(16) 0.0218(6) Uani 1 1 d . . .
C11 C 0.4019(3) 0.1788(4) 0.68571(17) 0.0201(6) Uani 1 1 d . . .
C12 C 0.3908(3) 0.2689(3) 0.60923(18) 0.0212(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02321(14) 0.01738(13) 0.02038(11) -0.00058(11) -0.00123(11) 0.01057(12)
F8 0.0241(8) 0.0344(9) 0.0272(8) -0.0065(7) -0.0080(6) 0.0133(7)
F9 0.0296(10) 0.0246(9) 0.0340(10) 0.0072(7) 0.0079(7) 0.0067(8)
F10 0.0407(10) 0.0423(10) 0.0207(8) 0.0098(7) 0.0038(7) 0.0300(8)
F11 0.0258(8) 0.0439(10) 0.0278(8) -0.0096(7) -0.0088(6) 0.0205(8)
F12 0.0284(9) 0.0212(9) 0.0356(9) 0.0006(7) 0.0063(7) 0.0057(7)
N1 0.0205(11) 0.0167(11) 0.0156(10) -0.0016(8) 0.0000(8) 0.0100(9)
N2 0.0316(13) 0.0223(13) 0.0177(9) 0.0040(12) 0.0022(11) 0.0158(12)
C1 0.0154(12) 0.0198(13) 0.0175(13) 0.0005(10) -0.0017(9) 0.0066(10)
C2 0.0198(13) 0.0234(14) 0.0180(13) -0.0015(10) -0.0023(10) 0.0068(11)
C3 0.0221(13) 0.0284(15) 0.0195(13) -0.0051(11) 0.0048(11) 0.0095(12)
C4 0.0228(16) 0.0225(14) 0.0279(16) -0.0053(12) 0.0005(11) 0.0123(13)
C5 0.0221(13) 0.0176(13) 0.0225(13) -0.0005(10) -0.0003(10) 0.0105(11)
C6 0.0315(15) 0.0267(14) 0.0178(12) 0.0016(10) 0.0061(11) 0.0199(13)
C7 0.0231(13) 0.0181(13) 0.0175(12) -0.0021(10) 0.0021(10) 0.0140(11)
C8 0.0183(13) 0.0233(14) 0.0177(13) -0.0048(10) -0.0028(10) 0.0111(11)
C9 0.0192(14) 0.0152(13) 0.0211(14) 0.0006(10) 0.0058(10) 0.0060(12)
C10 0.0337(16) 0.0301(15) 0.0120(12) 0.0018(11) 0.0036(11) 0.0238(14)
C11 0.0190(14) 0.0273(14) 0.0171(13) -0.0065(11) -0.0028(11) 0.0138(12)
C12 0.0233(14) 0.0208(14) 0.0213(14) -0.0017(11) 0.0048(11) 0.0124(12)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F8 C8 1.341(3) . ?
F9 C9 1.339(3) . ?
F10 C10 1.346(3) . ?
F11 C11 1.345(3) . ?
F12 C12 1.337(3) . ?
N1 C1 1.369(3) . ?
N1 C5 1.373(3) . ?
N1 C6 1.495(3) . ?
N2 C1 1.322(3) . ?
N2 H2A 0.909(17) . ?
N2 H2B 0.897(17) . ?
C1 C2 1.419(3) . ?
C2 C3 1.355(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.416(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.351(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.501(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.384(4) . ?
C7 C12 1.387(4) . ?
C8 C9 1.375(3) . ?
C9 C10 1.374(4) . ?
C10 C11 1.367(4) . ?
C11 C12 1.379(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 121.4(2) . . ?
C1 N1 C6 118.0(2) . . ?
C5 N1 C6 120.64(19) . . ?
C1 N2 H2A 121.9(18) . . ?
C1 N2 H2B 120.5(18) . . ?
H2A N2 H2B 117(2) . . ?
N2 C1 N1 121.0(3) . . ?
N2 C1 C2 121.6(3) . . ?
N1 C1 C2 117.4(2) . . ?
C3 C2 C1 121.0(2) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 N1 121.5(2) . . ?
C4 C5 H5 119.2 . . ?
N1 C5 H5 119.2 . . ?
N1 C6 C7 113.19(19) . . ?
N1 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N1 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C12 116.3(2) . . ?
C8 C7 C6 122.3(2) . . ?
C12 C7 C6 121.4(2) . . ?
F8 C8 C9 117.9(2) . . ?
F8 C8 C7 119.1(2) . . ?
C9 C8 C7 123.0(2) . . ?
F9 C9 C10 120.2(2) . . ?
F9 C9 C8 121.0(2) . . ?
C10 C9 C8 118.8(2) . . ?
F10 C10 C11 119.9(2) . . ?
F10 C10 C9 119.9(2) . . ?
C11 C10 C9 120.2(2) . . ?
F11 C11 C10 119.9(2) . . ?
F11 C11 C12 120.1(3) . . ?
C10 C11 C12 120.0(2) . . ?
F12 C12 C11 118.4(2) . . ?
F12 C12 C7 119.9(2) . . ?
C11 C12 C7 121.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 N2 177.4(2) . . . . ?
C6 N1 C1 N2 -2.5(3) . . . . ?
C5 N1 C1 C2 -2.9(3) . . . . ?
C6 N1 C1 C2 177.2(2) . . . . ?
N2 C1 C2 C3 -179.2(2) . . . . ?
N1 C1 C2 C3 1.1(4) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C3 C4 C5 N1 -0.8(4) . . . . ?
C1 N1 C5 C4 2.9(4) . . . . ?
C6 N1 C5 C4 -177.3(2) . . . . ?
C1 N1 C6 C7 -163.1(2) . . . . ?
C5 N1 C6 C7 17.0(3) . . . . ?
N1 C6 C7 C8 -91.9(3) . . . . ?
N1 C6 C7 C12 88.8(3) . . . . ?
C12 C7 C8 F8 179.1(2) . . . . ?
C6 C7 C8 F8 -0.3(3) . . . . ?
C12 C7 C8 C9 -0.6(4) . . . . ?
C6 C7 C8 C9 -179.9(2) . . . . ?
F8 C8 C9 F9 0.1(4) . . . . ?
C7 C8 C9 F9 179.8(2) . . . . ?
F8 C8 C9 C10 179.3(2) . . . . ?
C7 C8 C9 C10 -1.0(4) . . . . ?
F9 C9 C10 F10 1.2(4) . . . . ?
C8 C9 C10 F10 -178.0(2) . . . . ?
F9 C9 C10 C11 -178.5(2) . . . . ?
C8 C9 C10 C11 2.4(4) . . . . ?
F10 C10 C11 F11 -0.5(3) . . . . ?
C9 C10 C11 F11 179.1(2) . . . . ?
F10 C10 C11 C12 178.2(2) . . . . ?
C9 C10 C11 C12 -2.1(4) . . . . ?
F11 C11 C12 F12 -0.8(4) . . . . ?
C10 C11 C12 F12 -179.5(2) . . . . ?
F11 C11 C12 C7 179.2(2) . . . . ?
C10 C11 C12 C7 0.5(4) . . . . ?
C8 C7 C12 F12 -179.1(2) . . . . ?
C6 C7 C12 F12 0.2(4) . . . . ?
C8 C7 C12 C11 0.8(4) . . . . ?
C6 C7 C12 C11 -179.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A Br1 0.909(17) 2.459(19) 3.326(3) 160(2) .
N2 H2B Br1 0.897(17) 2.502(19) 3.370(3) 163(2) 3_564

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.21
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.065

_iucr_refine_instructions_details 
;
TITL mm-md-09-1 in P 31
CELL   0.71073   8.7299   8.7299  14.3094  90.000  90.000 120.000
ZERR     3       0.0001   0.0001   0.0003   0.000   0.000   0.000
LATT -1
SYMM -Y,X-Y,1/3+Z
SYMM -X+Y,-X,2/3+Z
SFAC        C       H       N       F       BR
UNIT        36      24       6      15       3
L.S.      10
OMIT -3 50.5
OMIT -2 2 5
OMIT 0 2 -5
TEMP  -150
SIZE  0.50 0.48 0.42
EQIV $1 -x+y, -x+1, z-1/3
HTAB N2 Br1
HTAB N2 Br1_$1
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.005600    0.110300
FVAR       0.52315
BR1   5    0.184882    0.692823    0.477996    11.00000    0.02321    0.01738 =
         0.02038   -0.00058   -0.00123    0.01057
F8    4   -0.045749   -0.039688    0.528234    11.00000    0.02409    0.03441 =
         0.02722   -0.00650   -0.00803    0.01332
F9    4   -0.025408   -0.215882    0.677812    11.00000    0.02959    0.02456 =
         0.03400    0.00715    0.00787    0.00667
F10   4    0.276623   -0.074437    0.780693    11.00000    0.04073    0.04232 =
         0.02073    0.00977    0.00380    0.03003
F11   4    0.549723    0.250186    0.737991    11.00000    0.02579    0.04390 =
         0.02778   -0.00960   -0.00881    0.02047
F12   4    0.528877    0.428117    0.589572    11.00000    0.02844    0.02118 =
         0.03560    0.00059    0.00626    0.00573
N1    3    0.299330    0.259756    0.382221    11.00000    0.02052    0.01669 =
         0.01558   -0.00160    0.00003    0.00996
N2    3    0.311337    0.509333    0.313958    11.00000    0.03161    0.02226 =
         0.01773    0.00397    0.00224    0.01576
H2A   2    0.282574    0.541535    0.368695    11.00000   -1.20000
H2B   2    0.339540    0.584880    0.265956    11.00000   -1.20000
DFIX 0.91 N2 H2A N2 H2B
C1    1    0.339250    0.374054    0.308753    11.00000    0.01544    0.01980 =
         0.01748    0.00051   -0.00165    0.00665
C2    1    0.412234    0.341986    0.227560    11.00000    0.01983    0.02341 =
         0.01800   -0.00147   -0.00226    0.00677
AFIX  43
H2    2    0.443336    0.420072    0.175772    11.00000   -1.20000
AFIX   0
C3    1    0.438223    0.201653    0.222797    11.00000    0.02212    0.02836 =
         0.01947   -0.00505    0.00479    0.00954
AFIX  43
H3    2    0.488687    0.182798    0.168268    11.00000   -1.20000
AFIX   0
C4    1    0.390182    0.083040    0.299087    11.00000    0.02279    0.02253 =
         0.02793   -0.00534    0.00046    0.01233
AFIX  43
H4    2    0.406081   -0.016846    0.296099    11.00000   -1.20000
AFIX   0
C5    1    0.321264    0.114964    0.376203    11.00000    0.02210    0.01760 =
         0.02246   -0.00046   -0.00032    0.01048
AFIX  43
H5    2    0.287195    0.035357    0.427451    11.00000   -1.20000
AFIX   0
C6    1    0.230316    0.296944    0.469777    11.00000    0.03155    0.02666 =
         0.01777    0.00157    0.00612    0.01989
AFIX  23
H6A   2    0.105370    0.264354    0.459966    11.00000   -1.20000
H6B   2    0.298587    0.425459    0.482823    11.00000   -1.20000
AFIX   0
C7    1    0.241259    0.198442    0.553152    11.00000    0.02311    0.01810 =
         0.01750   -0.00212    0.00210    0.01404
C8    1    0.103403    0.034288    0.579009    11.00000    0.01832    0.02332 =
         0.01766   -0.00484   -0.00275    0.01112
C9    1    0.111356   -0.057452    0.655174    11.00000    0.01916    0.01524 =
         0.02114    0.00060    0.00584    0.00604
C10   1    0.263748    0.015306    0.707484    11.00000    0.03371    0.03007 =
         0.01201    0.00179    0.00356    0.02376
C11   1    0.401852    0.178831    0.685713    11.00000    0.01895    0.02727 =
         0.01715   -0.00652   -0.00276    0.01379
C12   1    0.390797    0.268885    0.609227    11.00000    0.02335    0.02076 =
         0.02133   -0.00173    0.00477    0.01239
HKLF   4
 
REM  mm-md-09-1 in P 31
REM R1 =  0.0189 for   2116 Fo > 4sig(Fo)  and  0.0199 for all   2170 data
REM    187 parameters refined using      3 restraints
 
END
 
WGHT      0.0056      0.1104
REM Highest difference peak  0.197,  deepest hole -0.319,  1-sigma level  0.065
Q1    1   0.3648  0.5426  0.0788  11.00000  0.05    0.20
Q2    1   0.1389  0.5656  0.2530  11.00000  0.05    0.19
Q3    1   0.2924 -0.1072  0.6388  11.00000  0.05    0.18
Q4    1   0.2202  0.1945  0.2294  11.00000  0.05    0.18
Q5    1   0.3004  0.5451  0.5568  11.00000  0.05    0.18
Q6    1   0.6853  0.2015  0.6800  11.00000  0.05    0.18
Q7    1   0.1510 -0.2575  0.7378  11.00000  0.05    0.18
Q8    1   0.4832  0.6113  0.1225  11.00000  0.05    0.17
Q9    1   0.1714  0.1812  0.2785  11.00000  0.05    0.17
Q10   1   0.5643 -0.0818  0.2856  11.00000  0.05    0.17
Q11   1   0.3019 -0.0635  0.5583  11.00000  0.05    0.17
Q12   1   0.4058  0.2711  0.3836  11.00000  0.05    0.17
Q13   1   0.0067  0.3329  0.3583  11.00000  0.05    0.17
Q14   1   0.4991  0.3983  0.3860  11.00000  0.05    0.16
Q15   1   0.1421  0.2013  0.6816  11.00000  0.05    0.16
Q16   1   0.1753 -0.0735  0.4290  11.00000  0.05    0.16
Q17   1   0.0421 -0.1707  0.4223  11.00000  0.05    0.16
Q18   1   0.6628  0.2805  0.2425  11.00000  0.05    0.16
Q19   1   0.2024  0.7172  0.2960  11.00000  0.05    0.16
Q20   1   0.7809  0.4964  0.6367  11.00000  0.05    0.16
Q21   1   0.1909  0.1236  0.7191  11.00000  0.05    0.16
Q22   1   0.2736  0.2456  0.7030  11.00000  0.05    0.16
Q23   1   0.7153  0.5134  0.5437  11.00000  0.05    0.16
Q24   1   0.1724  0.0060  0.6908  11.00000  0.05    0.16
Q25   1   0.2950  0.3055  0.3399  11.00000  0.05    0.15
;
_database_code_depnum_ccdc_archive 'CCDC 1005273'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-bipy-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H10 F5 N2, H2 O, Br'
_chemical_formula_sum            'C17 H12 Br F5 N2 O'
_chemical_formula_weight         435.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.6652(3)
_cell_length_b                   14.6348(3)
_cell_length_c                   18.0643(3)
_cell_angle_alpha                77.611(2)
_cell_angle_beta                 73.769(2)
_cell_angle_gamma                75.674(2)
_cell_volume                     3319.49(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    13543
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1728
_exptl_absorpt_coefficient_mu    2.538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7020
_exptl_absorpt_correction_T_max  0.7854
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20164
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0689
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         25.25
_reflns_number_total             12016
_reflns_number_gt                8823
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, et al., 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+5.1532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         12016
_refine_ls_number_parameters     961
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.0909
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.84602(3) 0.32375(3) 0.59516(2) 0.02696(10) Uani 1 1 d . . .
F13 F 0.63430(17) 0.18302(16) 0.75716(12) 0.0302(5) Uani 1 1 d . . .
F14 F 0.56043(18) 0.37388(16) 0.73544(13) 0.0340(6) Uani 1 1 d . . .
F15 F 0.52702(16) 0.46468(15) 0.59426(13) 0.0306(5) Uani 1 1 d . . .
F16 F 0.5611(2) 0.36336(17) 0.47723(13) 0.0398(6) Uani 1 1 d . . .
F17 F 0.63926(19) 0.17423(17) 0.49706(13) 0.0378(6) Uani 1 1 d . . .
O1 O 0.9016(2) 0.2231(2) 0.43311(16) 0.0348(7) Uani 1 1 d D . .
H1D H 0.887(3) 0.254(3) 0.471(2) 0.052 Uiso 1 1 d D . .
H1E H 0.9669(15) 0.206(3) 0.423(2) 0.052 Uiso 1 1 d D . .
N1 N 0.7893(2) 0.0461(2) 0.65168(18) 0.0206(7) Uani 1 1 d . . .
N2 N 1.3068(3) -0.0810(2) 0.6954(2) 0.0316(8) Uani 1 1 d . . .
C1 C 0.8663(3) 0.0733(3) 0.5927(2) 0.0223(8) Uani 1 1 d . . .
H1 H 0.8502 0.1094 0.5457 0.027 Uiso 1 1 calc R . .
C2 C 0.9681(3) 0.0503(3) 0.5986(2) 0.0231(9) Uani 1 1 d . . .
H2 H 1.0213 0.0708 0.5562 0.028 Uiso 1 1 calc R . .
C3 C 0.9928(3) -0.0037(3) 0.6674(2) 0.0203(8) Uani 1 1 d . . .
C4 C 0.9105(3) -0.0308(3) 0.7274(2) 0.0240(9) Uani 1 1 d . . .
H4 H 0.9240 -0.0673 0.7750 0.029 Uiso 1 1 calc R . .
C5 C 0.8105(3) -0.0054(3) 0.7184(2) 0.0238(9) Uani 1 1 d . . .
H5 H 0.7556 -0.0245 0.7598 0.029 Uiso 1 1 calc R . .
C6 C 1.1016(3) -0.0303(3) 0.6762(2) 0.0212(8) Uani 1 1 d . . .
C7 C 1.1856(3) -0.0151(3) 0.6145(2) 0.0256(9) Uani 1 1 d . . .
H7 H 1.1749 0.0128 0.5641 0.031 Uiso 1 1 calc R . .
C8 C 1.2849(3) -0.0406(3) 0.6264(2) 0.0300(10) Uani 1 1 d . . .
H8 H 1.3411 -0.0289 0.5831 0.036 Uiso 1 1 calc R . .
C9 C 1.2258(3) -0.0952(3) 0.7549(2) 0.0296(9) Uani 1 1 d . . .
H9 H 1.2390 -0.1233 0.8046 0.035 Uiso 1 1 calc R . .
C10 C 1.1240(3) -0.0714(3) 0.7485(2) 0.0270(9) Uani 1 1 d . . .
H10 H 1.0693 -0.0828 0.7930 0.032 Uiso 1 1 calc R . .
C11 C 0.6810(3) 0.0679(3) 0.6417(2) 0.0238(9) Uani 1 1 d . . .
H11A H 0.6356 0.0385 0.6890 0.029 Uiso 1 1 calc R . .
H11B H 0.6796 0.0398 0.5969 0.029 Uiso 1 1 calc R . .
C12 C 0.6396(3) 0.1735(3) 0.6279(2) 0.0221(8) Uani 1 1 d . . .
C13 C 0.6164(3) 0.2274(3) 0.6872(2) 0.0216(8) Uani 1 1 d . . .
C14 C 0.5778(3) 0.3238(3) 0.6776(2) 0.0222(8) Uani 1 1 d . . .
C15 C 0.5607(3) 0.3690(3) 0.6063(2) 0.0238(9) Uani 1 1 d . . .
C16 C 0.5803(3) 0.3185(3) 0.5459(2) 0.0271(9) Uani 1 1 d . . .
C17 C 0.6196(3) 0.2222(3) 0.5580(2) 0.0240(9) Uani 1 1 d . . .
Br1A Br 0.90593(3) 0.37849(3) 0.91961(2) 0.02829(10) Uani 1 1 d . . .
F13A F 0.70351(19) 0.10278(17) 1.04640(14) 0.0419(6) Uani 1 1 d . . .
F14A F 0.6034(2) 0.2462(2) 1.12980(14) 0.0550(8) Uani 1 1 d . . .
F15A F 0.5640(2) 0.4284(2) 1.05552(16) 0.0523(7) Uani 1 1 d . . .
F16A F 0.62917(19) 0.46834(17) 0.89699(15) 0.0423(6) Uani 1 1 d . . .
F17A F 0.72912(17) 0.32522(16) 0.81519(13) 0.0325(5) Uani 1 1 d . . .
O1A O 0.8846(2) 0.1918(2) 1.06579(19) 0.0450(8) Uani 1 1 d D . .
H1F H 0.9483(19) 0.171(3) 1.066(3) 0.067 Uiso 1 1 d D . .
H1G H 0.883(4) 0.241(2) 1.032(2) 0.067 Uiso 1 1 d D . .
N1A N 0.8913(2) 0.1390(2) 0.85570(17) 0.0219(7) Uani 1 1 d . . .
N2A N 1.4327(3) 0.1236(3) 0.7446(2) 0.0327(8) Uani 1 1 d . . .
C1A C 0.9341(3) 0.1778(3) 0.7828(2) 0.0261(9) Uani 1 1 d . . .
H1A H 0.8922 0.2034 0.7463 0.031 Uiso 1 1 calc R . .
C2A C 1.0379(3) 0.1806(3) 0.7610(2) 0.0248(9) Uani 1 1 d . . .
H2A H 1.0669 0.2086 0.7094 0.030 Uiso 1 1 calc R . .
C3A C 1.1017(3) 0.1433(3) 0.8129(2) 0.0216(8) Uani 1 1 d . . .
C4A C 1.0523(3) 0.1075(3) 0.8894(2) 0.0270(9) Uani 1 1 d . . .
H4A H 1.0913 0.0847 0.9280 0.032 Uiso 1 1 calc R . .
C5A C 0.9489(3) 0.1051(3) 0.9087(2) 0.0279(9) Uani 1 1 d . . .
H5A H 0.9173 0.0793 0.9603 0.033 Uiso 1 1 calc R . .
C6A C 1.2153(3) 0.1391(3) 0.7895(2) 0.0226(8) Uani 1 1 d . . .
C7A C 1.2665(3) 0.1650(3) 0.7127(2) 0.0294(9) Uani 1 1 d . . .
H7A H 1.2286 0.1888 0.6734 0.035 Uiso 1 1 calc R . .
C8A C 1.3734(3) 0.1557(3) 0.6938(2) 0.0317(10) Uani 1 1 d . . .
H8A H 1.4067 0.1736 0.6408 0.038 Uiso 1 1 calc R . .
C9A C 1.3826(3) 0.1008(3) 0.8185(2) 0.0374(11) Uani 1 1 d . . .
H9A H 1.4227 0.0779 0.8564 0.045 Uiso 1 1 calc R . .
C10A C 1.2762(3) 0.1080(3) 0.8437(2) 0.0341(10) Uani 1 1 d . . .
H10A H 1.2450 0.0919 0.8976 0.041 Uiso 1 1 calc R . .
C11A C 0.7793(3) 0.1339(3) 0.8800(2) 0.0269(9) Uani 1 1 d . . .
H11C H 0.7711 0.0704 0.9108 0.032 Uiso 1 1 calc R . .
H11D H 0.7521 0.1419 0.8332 0.032 Uiso 1 1 calc R . .
C12A C 0.7180(3) 0.2103(3) 0.9282(2) 0.0251(9) Uani 1 1 d . . .
C13A C 0.6851(3) 0.1934(3) 1.0090(2) 0.0312(10) Uani 1 1 d . . .
C14A C 0.6333(3) 0.2652(3) 1.0518(2) 0.0352(11) Uani 1 1 d . . .
C15A C 0.6129(3) 0.3580(3) 1.0139(3) 0.0365(11) Uani 1 1 d . . .
C16A C 0.6452(3) 0.3770(3) 0.9341(2) 0.0308(10) Uani 1 1 d . . .
C17A C 0.6962(3) 0.3044(3) 0.8933(2) 0.0268(9) Uani 1 1 d . . .
Br1B Br 0.85962(3) 0.87748(3) 0.93426(2) 0.02966(11) Uani 1 1 d . . .
F13B F 0.68020(19) 0.58127(17) 1.02744(14) 0.0400(6) Uani 1 1 d . . .
F14B F 0.5407(2) 0.7123(2) 1.10879(14) 0.0497(7) Uani 1 1 d . . .
F15B F 0.48943(19) 0.8942(2) 1.03757(16) 0.0508(7) Uani 1 1 d . . .
F16B F 0.5851(2) 0.94721(17) 0.88482(15) 0.0448(7) Uani 1 1 d . . .
F17B F 0.72448(17) 0.81587(15) 0.80505(12) 0.0301(5) Uani 1 1 d . . .
O1B O 0.8424(2) 0.6719(2) 1.07044(18) 0.0408(8) Uani 1 1 d D . .
H1H H 0.903(2) 0.663(3) 1.076(3) 0.061 Uiso 1 1 d D . .
H1I H 0.836(3) 0.720(3) 1.035(2) 0.061 Uiso 1 1 d D . .
N1B N 0.8902(2) 0.6394(2) 0.84527(17) 0.0211(7) Uani 1 1 d . . .
N2B N 1.4316(2) 0.6065(2) 0.73128(19) 0.0276(8) Uani 1 1 d . . .
C1B C 0.9345(3) 0.6746(3) 0.7714(2) 0.0239(9) Uani 1 1 d . . .
H1B H 0.8933 0.6983 0.7343 0.029 Uiso 1 1 calc R . .
C2B C 1.0380(3) 0.6766(3) 0.7496(2) 0.0235(9) Uani 1 1 d . . .
H2B H 1.0683 0.7020 0.6975 0.028 Uiso 1 1 calc R . .
C3B C 1.0995(3) 0.6414(3) 0.8033(2) 0.0210(8) Uani 1 1 d . . .
C4B C 1.0497(3) 0.6125(3) 0.8805(2) 0.0235(9) Uani 1 1 d . . .
H4B H 1.0880 0.5938 0.9197 0.028 Uiso 1 1 calc R . .
C5B C 0.9461(3) 0.6111(3) 0.9000(2) 0.0235(9) Uani 1 1 d . . .
H5B H 0.9130 0.5899 0.9524 0.028 Uiso 1 1 calc R . .
C6B C 1.2136(3) 0.6318(3) 0.7788(2) 0.0215(8) Uani 1 1 d . . .
C7B C 1.2625(3) 0.6881(3) 0.7134(2) 0.0259(9) Uani 1 1 d . . .
H7B H 1.2226 0.7359 0.6829 0.031 Uiso 1 1 calc R . .
C8B C 1.3695(3) 0.6737(3) 0.6934(2) 0.0295(9) Uani 1 1 d . . .
H8B H 1.4013 0.7144 0.6495 0.035 Uiso 1 1 calc R . .
C9B C 1.3851(3) 0.5511(3) 0.7931(2) 0.0297(10) Uani 1 1 d . . .
H9B H 1.4274 0.5020 0.8208 0.036 Uiso 1 1 calc R . .
C10B C 1.2775(3) 0.5617(3) 0.8189(2) 0.0279(9) Uani 1 1 d . . .
H10B H 1.2479 0.5211 0.8637 0.034 Uiso 1 1 calc R . .
C11B C 0.7814(3) 0.6245(3) 0.8662(2) 0.0248(9) Uani 1 1 d . . .
H11E H 0.7793 0.5594 0.8960 0.030 Uiso 1 1 calc R . .
H11F H 0.7594 0.6283 0.8177 0.030 Uiso 1 1 calc R . .
C12B C 0.7055(3) 0.6958(3) 0.9140(2) 0.0215(8) Uani 1 1 d . . .
C13B C 0.6579(3) 0.6716(3) 0.9919(2) 0.0270(9) Uani 1 1 d . . .
C14B C 0.5860(3) 0.7376(3) 1.0332(2) 0.0332(10) Uani 1 1 d . . .
C15B C 0.5606(3) 0.8303(3) 0.9971(3) 0.0351(10) Uani 1 1 d . . .
C16B C 0.6075(3) 0.8561(3) 0.9203(2) 0.0291(9) Uani 1 1 d . . .
C17B C 0.6787(3) 0.7895(3) 0.8804(2) 0.0240(9) Uani 1 1 d . . .
Br1C Br 0.84009(3) 0.83447(3) 0.58800(2) 0.02762(10) Uani 1 1 d . . .
F13C F 0.61800(17) 0.67117(16) 0.76258(12) 0.0295(5) Uani 1 1 d . . .
F14C F 0.53805(18) 0.86125(17) 0.75631(14) 0.0358(6) Uani 1 1 d . . .
F15C F 0.51789(17) 0.97062(15) 0.61786(14) 0.0336(6) Uani 1 1 d . . .
F16C F 0.56793(19) 0.88977(17) 0.48765(13) 0.0391(6) Uani 1 1 d . . .
F17C F 0.64804(18) 0.70174(17) 0.49241(12) 0.0356(6) Uani 1 1 d . . .
O1C O 0.8971(2) 0.7383(2) 0.42545(16) 0.0343(7) Uani 1 1 d D . .
H1J H 0.9617(15) 0.723(3) 0.419(3) 0.051 Uiso 1 1 d D . .
H1K H 0.874(3) 0.773(3) 0.460(2) 0.051 Uiso 1 1 d D . .
N1C N 0.7881(2) 0.5520(2) 0.64028(17) 0.0191(7) Uani 1 1 d . . .
N2C N 1.3125(3) 0.4183(2) 0.6708(2) 0.0325(8) Uani 1 1 d . . .
C1C C 0.8635(3) 0.5829(3) 0.5804(2) 0.0205(8) Uani 1 1 d . . .
H1C H 0.8459 0.6215 0.5347 0.025 Uiso 1 1 calc R . .
C2C C 0.9655(3) 0.5584(3) 0.5855(2) 0.0221(8) Uani 1 1 d . . .
H2C H 1.0178 0.5808 0.5433 0.026 Uiso 1 1 calc R . .
C3C C 0.9934(3) 0.5008(3) 0.6519(2) 0.0198(8) Uani 1 1 d . . .
C4C C 0.9129(3) 0.4711(3) 0.7123(2) 0.0218(8) Uani 1 1 d . . .
H4C H 0.9279 0.4329 0.7589 0.026 Uiso 1 1 calc R . .
C5C C 0.8125(3) 0.4968(3) 0.7046(2) 0.0221(8) Uani 1 1 d . . .
H5C H 0.7588 0.4749 0.7458 0.027 Uiso 1 1 calc R . .
C6C C 1.1037(3) 0.4727(3) 0.6590(2) 0.0217(8) Uani 1 1 d . . .
C7C C 1.1848(3) 0.4984(3) 0.5978(2) 0.0280(9) Uani 1 1 d . . .
H7C H 1.1707 0.5354 0.5505 0.034 Uiso 1 1 calc R . .
C8C C 1.2855(3) 0.4699(3) 0.6062(2) 0.0305(10) Uani 1 1 d . . .
H8C H 1.3394 0.4880 0.5633 0.037 Uiso 1 1 calc R . .
C9C C 1.2337(3) 0.3953(3) 0.7300(2) 0.0301(10) Uani 1 1 d . . .
H9C H 1.2498 0.3599 0.7771 0.036 Uiso 1 1 calc R . .
C10C C 1.1300(3) 0.4199(3) 0.7267(2) 0.0280(9) Uani 1 1 d . . .
H10C H 1.0776 0.4009 0.7704 0.034 Uiso 1 1 calc R . .
C11C C 0.6787(3) 0.5758(3) 0.6320(2) 0.0253(9) Uani 1 1 d . . .
H11G H 0.6351 0.5410 0.6772 0.030 Uiso 1 1 calc R . .
H11H H 0.6764 0.5547 0.5841 0.030 Uiso 1 1 calc R . .
C12C C 0.6356(3) 0.6814(3) 0.6276(2) 0.0207(8) Uani 1 1 d . . .
C13C C 0.6052(3) 0.7249(3) 0.6938(2) 0.0224(8) Uani 1 1 d . . .
C14C C 0.5640(3) 0.8205(3) 0.6921(2) 0.0245(9) Uani 1 1 d . . .
C15C C 0.5523(3) 0.8763(3) 0.6224(2) 0.0256(9) Uani 1 1 d . . .
C16C C 0.5794(3) 0.8354(3) 0.5558(2) 0.0268(9) Uani 1 1 d . . .
C17C C 0.6208(3) 0.7392(3) 0.5592(2) 0.0233(9) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0257(2) 0.0270(2) 0.0274(2) -0.00635(17) -0.00163(16) -0.00740(16)
F13 0.0351(13) 0.0293(13) 0.0263(12) -0.0002(10) -0.0161(10) -0.0004(10)
F14 0.0421(14) 0.0267(13) 0.0355(13) -0.0134(11) -0.0138(11) 0.0012(11)
F15 0.0263(12) 0.0188(12) 0.0457(14) 0.0000(11) -0.0137(11) -0.0010(9)
F16 0.0523(16) 0.0365(14) 0.0310(13) 0.0050(11) -0.0205(12) -0.0063(12)
F17 0.0503(16) 0.0376(14) 0.0296(13) -0.0104(11) -0.0137(12) -0.0070(12)
O1 0.0362(17) 0.045(2) 0.0221(15) -0.0008(14) -0.0067(13) -0.0107(15)
N1 0.0196(16) 0.0158(16) 0.0259(17) -0.0039(14) -0.0046(14) -0.0028(13)
N2 0.032(2) 0.0247(19) 0.040(2) -0.0049(17) -0.0123(17) -0.0045(15)
C1 0.023(2) 0.020(2) 0.023(2) 0.0001(17) -0.0046(17) -0.0064(16)
C2 0.023(2) 0.023(2) 0.023(2) -0.0036(17) -0.0029(16) -0.0073(16)
C3 0.023(2) 0.0163(19) 0.024(2) -0.0069(16) -0.0067(16) -0.0036(15)
C4 0.025(2) 0.023(2) 0.020(2) 0.0026(17) -0.0032(17) -0.0051(16)
C5 0.024(2) 0.020(2) 0.026(2) -0.0020(17) -0.0021(17) -0.0056(16)
C6 0.027(2) 0.0121(18) 0.025(2) -0.0036(16) -0.0076(17) -0.0030(15)
C7 0.026(2) 0.027(2) 0.025(2) -0.0047(18) -0.0057(17) -0.0067(17)
C8 0.023(2) 0.031(2) 0.037(2) -0.006(2) -0.0031(18) -0.0098(18)
C9 0.029(2) 0.028(2) 0.032(2) 0.0009(19) -0.0145(19) -0.0035(18)
C10 0.027(2) 0.023(2) 0.029(2) -0.0039(18) -0.0056(18) -0.0014(17)
C11 0.0178(19) 0.022(2) 0.033(2) -0.0003(18) -0.0084(17) -0.0076(16)
C12 0.0150(18) 0.023(2) 0.029(2) -0.0043(18) -0.0041(16) -0.0058(15)
C13 0.0156(19) 0.023(2) 0.024(2) 0.0009(17) -0.0066(16) -0.0032(15)
C14 0.0177(19) 0.023(2) 0.027(2) -0.0094(18) -0.0045(16) -0.0020(16)
C15 0.0175(19) 0.019(2) 0.035(2) 0.0007(18) -0.0102(17) -0.0035(15)
C16 0.024(2) 0.030(2) 0.026(2) 0.0039(19) -0.0108(17) -0.0054(17)
C17 0.023(2) 0.028(2) 0.021(2) -0.0064(18) -0.0038(16) -0.0054(17)
Br1A 0.0305(2) 0.0263(2) 0.0268(2) 0.00122(17) -0.01067(17) -0.00365(16)
F13A 0.0440(15) 0.0357(15) 0.0390(14) 0.0120(12) -0.0084(12) -0.0123(12)
F14A 0.0492(17) 0.072(2) 0.0299(14) -0.0029(14) 0.0028(12) -0.0060(15)
F15A 0.0429(16) 0.0543(18) 0.0533(17) -0.0232(15) -0.0054(13) 0.0076(13)
F16A 0.0382(15) 0.0257(14) 0.0550(16) -0.0012(12) -0.0100(12) 0.0021(11)
F17A 0.0336(13) 0.0281(13) 0.0311(13) 0.0061(10) -0.0089(11) -0.0055(10)
O1A 0.0369(18) 0.053(2) 0.0400(19) 0.0109(16) -0.0099(16) -0.0144(16)
N1A 0.0239(17) 0.0186(17) 0.0247(17) -0.0021(14) -0.0073(14) -0.0064(13)
N2A 0.0287(19) 0.036(2) 0.031(2) -0.0074(17) -0.0036(16) -0.0046(16)
C1A 0.031(2) 0.028(2) 0.020(2) -0.0025(18) -0.0103(17) -0.0025(18)
C2A 0.030(2) 0.024(2) 0.0184(19) -0.0007(17) -0.0051(17) -0.0038(17)
C3A 0.029(2) 0.016(2) 0.0205(19) -0.0070(16) -0.0072(17) -0.0011(16)
C4A 0.029(2) 0.029(2) 0.025(2) -0.0026(18) -0.0123(18) -0.0039(17)
C5A 0.029(2) 0.032(2) 0.023(2) 0.0017(18) -0.0081(18) -0.0091(18)
C6A 0.029(2) 0.018(2) 0.022(2) -0.0035(16) -0.0070(17) -0.0032(16)
C7A 0.031(2) 0.037(2) 0.021(2) -0.0033(19) -0.0075(18) -0.0079(19)
C8A 0.029(2) 0.041(3) 0.023(2) -0.006(2) 0.0019(18) -0.0117(19)
C9A 0.029(2) 0.049(3) 0.030(2) 0.004(2) -0.011(2) -0.004(2)
C10A 0.030(2) 0.048(3) 0.018(2) 0.005(2) -0.0033(18) -0.008(2)
C11A 0.023(2) 0.027(2) 0.032(2) 0.0003(18) -0.0122(18) -0.0049(17)
C12A 0.019(2) 0.025(2) 0.030(2) 0.0059(18) -0.0097(17) -0.0066(16)
C13A 0.020(2) 0.034(2) 0.035(2) 0.008(2) -0.0087(18) -0.0085(18)
C14A 0.029(2) 0.048(3) 0.024(2) -0.002(2) -0.0001(18) -0.009(2)
C15A 0.021(2) 0.039(3) 0.048(3) -0.015(2) -0.004(2) -0.0013(19)
C16A 0.027(2) 0.024(2) 0.039(2) 0.002(2) -0.0129(19) -0.0025(18)
C17A 0.017(2) 0.032(2) 0.028(2) 0.0034(19) -0.0039(17) -0.0062(17)
Br1B 0.0365(2) 0.0294(2) 0.0239(2) 0.00052(18) -0.01166(17) -0.00695(17)
F13B 0.0463(16) 0.0337(14) 0.0365(14) 0.0138(12) -0.0125(12) -0.0152(12)
F14B 0.0471(17) 0.070(2) 0.0292(14) -0.0076(13) 0.0043(12) -0.0224(14)
F15B 0.0358(15) 0.0554(18) 0.0607(18) -0.0368(15) -0.0001(13) 0.0026(13)
F16B 0.0500(16) 0.0241(14) 0.0566(17) -0.0075(12) -0.0179(13) 0.0063(11)
F17B 0.0352(13) 0.0247(12) 0.0265(12) 0.0047(10) -0.0061(10) -0.0081(10)
O1B 0.0351(18) 0.051(2) 0.0324(17) 0.0012(15) -0.0084(15) -0.0082(16)
N1B 0.0223(17) 0.0200(17) 0.0205(16) -0.0032(14) -0.0066(14) -0.0014(13)
N2B 0.0223(18) 0.033(2) 0.0274(18) -0.0086(16) -0.0035(15) -0.0042(15)
C1B 0.027(2) 0.022(2) 0.021(2) -0.0032(17) -0.0078(17) -0.0013(17)
C2B 0.023(2) 0.028(2) 0.0173(19) -0.0020(17) -0.0021(16) -0.0046(16)
C3B 0.021(2) 0.022(2) 0.022(2) -0.0056(17) -0.0070(16) -0.0034(16)
C4B 0.023(2) 0.028(2) 0.021(2) -0.0017(17) -0.0075(16) -0.0054(16)
C5B 0.023(2) 0.026(2) 0.021(2) -0.0022(17) -0.0052(17) -0.0059(17)
C6B 0.024(2) 0.021(2) 0.0212(19) -0.0078(17) -0.0064(16) -0.0024(16)
C7B 0.024(2) 0.025(2) 0.028(2) -0.0049(18) -0.0070(17) -0.0024(17)
C8B 0.031(2) 0.031(2) 0.027(2) -0.0048(19) -0.0017(18) -0.0133(19)
C9B 0.022(2) 0.034(2) 0.030(2) -0.004(2) -0.0068(18) -0.0001(18)
C10B 0.023(2) 0.033(2) 0.024(2) -0.0009(18) -0.0038(17) -0.0042(17)
C11B 0.018(2) 0.022(2) 0.037(2) -0.0032(18) -0.0096(17) -0.0050(16)
C12B 0.0163(19) 0.023(2) 0.025(2) 0.0019(17) -0.0068(16) -0.0063(15)
C13B 0.022(2) 0.031(2) 0.028(2) 0.0026(19) -0.0087(17) -0.0091(17)
C14B 0.026(2) 0.052(3) 0.023(2) -0.008(2) 0.0013(18) -0.017(2)
C15B 0.024(2) 0.041(3) 0.041(3) -0.016(2) -0.006(2) -0.0016(19)
C16B 0.030(2) 0.020(2) 0.039(2) -0.0038(19) -0.0133(19) -0.0020(17)
C17B 0.025(2) 0.024(2) 0.024(2) -0.0020(17) -0.0067(17) -0.0055(17)
Br1C 0.0262(2) 0.0271(2) 0.0298(2) -0.00836(18) -0.00283(17) -0.00671(16)
F13C 0.0342(13) 0.0297(13) 0.0250(12) 0.0013(10) -0.0146(10) -0.0038(10)
F14C 0.0364(14) 0.0336(14) 0.0415(14) -0.0153(12) -0.0168(11) 0.0022(11)
F15C 0.0290(13) 0.0195(12) 0.0532(15) 0.0007(11) -0.0182(11) -0.0026(10)
F16C 0.0443(15) 0.0352(14) 0.0315(13) 0.0149(11) -0.0153(11) -0.0069(11)
F17C 0.0385(14) 0.0431(15) 0.0231(12) -0.0064(11) -0.0041(10) -0.0067(11)
O1C 0.0319(16) 0.045(2) 0.0255(16) -0.0055(14) -0.0059(13) -0.0081(15)
N1C 0.0166(16) 0.0160(16) 0.0230(17) -0.0007(14) -0.0031(13) -0.0041(12)
N2C 0.0249(19) 0.031(2) 0.041(2) -0.0049(17) -0.0099(17) -0.0032(15)
C1C 0.024(2) 0.019(2) 0.0181(19) -0.0008(16) -0.0051(16) -0.0060(16)
C2C 0.023(2) 0.020(2) 0.0213(19) -0.0003(16) -0.0038(16) -0.0059(16)
C3C 0.023(2) 0.0157(19) 0.0214(19) -0.0043(16) -0.0064(16) -0.0028(15)
C4C 0.020(2) 0.023(2) 0.0220(19) 0.0000(17) -0.0048(16) -0.0063(16)
C5C 0.021(2) 0.022(2) 0.0198(19) -0.0029(17) 0.0015(16) -0.0057(16)
C6C 0.023(2) 0.0161(19) 0.026(2) -0.0048(17) -0.0055(17) -0.0030(16)
C7C 0.024(2) 0.033(2) 0.026(2) 0.0012(18) -0.0077(17) -0.0046(17)
C8C 0.021(2) 0.034(2) 0.033(2) -0.003(2) -0.0021(18) -0.0077(18)
C9C 0.028(2) 0.029(2) 0.031(2) -0.0012(19) -0.0081(19) -0.0049(18)
C10C 0.027(2) 0.027(2) 0.027(2) -0.0010(18) -0.0046(18) -0.0045(17)
C11C 0.0164(19) 0.027(2) 0.036(2) -0.0057(19) -0.0075(17) -0.0085(16)
C12C 0.0145(18) 0.023(2) 0.025(2) 0.0012(17) -0.0057(16) -0.0073(15)
C13C 0.020(2) 0.023(2) 0.024(2) 0.0032(17) -0.0092(16) -0.0047(16)
C14C 0.020(2) 0.030(2) 0.027(2) -0.0065(19) -0.0097(17) -0.0050(17)
C15C 0.018(2) 0.018(2) 0.042(2) -0.0003(19) -0.0117(18) -0.0049(16)
C16C 0.023(2) 0.026(2) 0.030(2) 0.0079(19) -0.0123(18) -0.0077(17)
C17C 0.018(2) 0.030(2) 0.022(2) -0.0022(18) -0.0052(16) -0.0063(16)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F13 C13 1.349(4) . ?
F14 C14 1.337(4) . ?
F15 C15 1.351(4) . ?
F16 C16 1.337(4) . ?
F17 C17 1.360(4) . ?
O1 H1D 0.85(2) . ?
O1 H1E 0.84(2) . ?
N1 C1 1.342(5) . ?
N1 C5 1.343(5) . ?
N1 C11 1.488(5) . ?
N2 C9 1.333(5) . ?
N2 C8 1.340(5) . ?
C1 C2 1.376(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.402(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(5) . ?
C3 C6 1.485(5) . ?
C4 C5 1.371(5) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.383(5) . ?
C6 C10 1.398(5) . ?
C7 C8 1.380(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.380(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.500(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.373(5) . ?
C12 C13 1.386(5) . ?
C13 C14 1.370(5) . ?
C14 C15 1.371(5) . ?
C15 C16 1.376(5) . ?
C16 C17 1.372(5) . ?
F13A C13A 1.350(5) . ?
F14A C14A 1.339(5) . ?
F15A C15A 1.336(5) . ?
F16A C16A 1.355(5) . ?
F17A C17A 1.348(4) . ?
O1A H1F 0.85(2) . ?
O1A H1G 0.85(2) . ?
N1A C5A 1.345(5) . ?
N1A C1A 1.346(5) . ?
N1A C11A 1.486(5) . ?
N2A C8A 1.328(5) . ?
N2A C9A 1.331(5) . ?
C1A C2A 1.370(5) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.393(5) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.409(5) . ?
C3A C6A 1.480(5) . ?
C4A C5A 1.364(6) . ?
C4A H4A 0.9500 . ?
C5A H5A 0.9500 . ?
C6A C7A 1.387(5) . ?
C6A C10A 1.392(5) . ?
C7A C8A 1.382(6) . ?
C7A H7A 0.9500 . ?
C8A H8A 0.9500 . ?
C9A C10A 1.380(6) . ?
C9A H9A 0.9500 . ?
C10A H10A 0.9500 . ?
C11A C12A 1.502(6) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C12A C17A 1.384(5) . ?
C12A C13A 1.388(6) . ?
C13A C14A 1.371(6) . ?
C14A C15A 1.383(6) . ?
C15A C16A 1.373(6) . ?
C16A C17A 1.356(6) . ?
F13B C13B 1.341(4) . ?
F14B C14B 1.345(4) . ?
F15B C15B 1.342(5) . ?
F16B C16B 1.350(4) . ?
F17B C17B 1.345(4) . ?
O1B H1H 0.84(2) . ?
O1B H1I 0.84(2) . ?
N1B C1B 1.349(5) . ?
N1B C5B 1.349(5) . ?
N1B C11B 1.487(5) . ?
N2B C8B 1.333(5) . ?
N2B C9B 1.334(5) . ?
C1B C2B 1.364(5) . ?
C1B H1B 0.9500 . ?
C2B C3B 1.393(5) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.396(5) . ?
C3B C6B 1.477(5) . ?
C4B C5B 1.364(5) . ?
C4B H4B 0.9500 . ?
C5B H5B 0.9500 . ?
C6B C10B 1.390(5) . ?
C6B C7B 1.390(5) . ?
C7B C8B 1.378(5) . ?
C7B H7B 0.9500 . ?
C8B H8B 0.9500 . ?
C9B C10B 1.392(5) . ?
C9B H9B 0.9500 . ?
C10B H10B 0.9500 . ?
C11B C12B 1.503(5) . ?
C11B H11E 0.9900 . ?
C11B H11F 0.9900 . ?
C12B C17B 1.380(5) . ?
C12B C13B 1.385(5) . ?
C13B C14B 1.372(6) . ?
C14B C15B 1.380(6) . ?
C15B C16B 1.369(6) . ?
C16B C17B 1.363(5) . ?
F13C C13C 1.351(4) . ?
F14C C14C 1.338(4) . ?
F15C C15C 1.337(4) . ?
F16C C16C 1.341(4) . ?
F17C C17C 1.351(4) . ?
O1C H1J 0.84(2) . ?
O1C H1K 0.84(2) . ?
N1C C5C 1.340(5) . ?
N1C C1C 1.354(5) . ?
N1C C11C 1.491(4) . ?
N2C C8C 1.340(5) . ?
N2C C9C 1.341(5) . ?
C1C C2C 1.375(5) . ?
C1C H1C 0.9500 . ?
C2C C3C 1.399(5) . ?
C2C H2C 0.9500 . ?
C3C C4C 1.397(5) . ?
C3C C6C 1.495(5) . ?
C4C C5C 1.367(5) . ?
C4C H4C 0.9500 . ?
C5C H5C 0.9500 . ?
C6C C10C 1.388(5) . ?
C6C C7C 1.391(5) . ?
C7C C8C 1.378(5) . ?
C7C H7C 0.9500 . ?
C8C H8C 0.9500 . ?
C9C C10C 1.387(5) . ?
C9C H9C 0.9500 . ?
C10C H10C 0.9500 . ?
C11C C12C 1.505(5) . ?
C11C H11G 0.9900 . ?
C11C H11H 0.9900 . ?
C12C C17C 1.375(5) . ?
C12C C13C 1.388(5) . ?
C13C C14C 1.371(5) . ?
C14C C15C 1.372(5) . ?
C15C C16C 1.375(6) . ?
C16C C17C 1.376(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1D O1 H1E 105(3) . . ?
C1 N1 C5 120.1(3) . . ?
C1 N1 C11 120.1(3) . . ?
C5 N1 C11 119.7(3) . . ?
C9 N2 C8 116.3(3) . . ?
N1 C1 C2 121.6(4) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 117.0(3) . . ?
C4 C3 C6 121.6(3) . . ?
C2 C3 C6 121.4(3) . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
N1 C5 C4 120.8(3) . . ?
N1 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C10 116.5(4) . . ?
C7 C6 C3 122.5(3) . . ?
C10 C6 C3 121.1(3) . . ?
C8 C7 C6 119.8(4) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
N2 C8 C7 123.9(4) . . ?
N2 C8 H8 118.0 . . ?
C7 C8 H8 118.0 . . ?
N2 C9 C10 123.7(4) . . ?
N2 C9 H9 118.1 . . ?
C10 C9 H9 118.1 . . ?
C9 C10 C6 119.8(4) . . ?
C9 C10 H10 120.1 . . ?
C6 C10 H10 120.1 . . ?
N1 C11 C12 111.6(3) . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C17 C12 C13 116.0(3) . . ?
C17 C12 C11 123.2(3) . . ?
C13 C12 C11 120.8(3) . . ?
F13 C13 C14 118.6(3) . . ?
F13 C13 C12 118.4(3) . . ?
C14 C13 C12 123.0(3) . . ?
F14 C14 C13 121.1(3) . . ?
F14 C14 C15 120.3(3) . . ?
C13 C14 C15 118.6(3) . . ?
F15 C15 C14 119.8(3) . . ?
F15 C15 C16 119.4(3) . . ?
C14 C15 C16 120.7(3) . . ?
F16 C16 C17 121.4(4) . . ?
F16 C16 C15 120.0(3) . . ?
C17 C16 C15 118.6(3) . . ?
F17 C17 C16 117.3(3) . . ?
F17 C17 C12 119.6(3) . . ?
C16 C17 C12 123.1(4) . . ?
H1F O1A H1G 105(3) . . ?
C5A N1A C1A 120.5(3) . . ?
C5A N1A C11A 118.4(3) . . ?
C1A N1A C11A 121.1(3) . . ?
C8A N2A C9A 115.6(4) . . ?
N1A C1A C2A 120.4(4) . . ?
N1A C1A H1A 119.8 . . ?
C2A C1A H1A 119.8 . . ?
C1A C2A C3A 121.3(4) . . ?
C1A C2A H2A 119.4 . . ?
C3A C2A H2A 119.4 . . ?
C2A C3A C4A 116.2(4) . . ?
C2A C3A C6A 122.5(3) . . ?
C4A C3A C6A 121.3(3) . . ?
C5A C4A C3A 120.7(4) . . ?
C5A C4A H4A 119.6 . . ?
C3A C4A H4A 119.6 . . ?
N1A C5A C4A 120.9(4) . . ?
N1A C5A H5A 119.6 . . ?
C4A C5A H5A 119.6 . . ?
C7A C6A C10A 116.6(4) . . ?
C7A C6A C3A 121.9(3) . . ?
C10A C6A C3A 121.4(3) . . ?
C8A C7A C6A 119.3(4) . . ?
C8A C7A H7A 120.4 . . ?
C6A C7A H7A 120.4 . . ?
N2A C8A C7A 124.6(4) . . ?
N2A C8A H8A 117.7 . . ?
C7A C8A H8A 117.7 . . ?
N2A C9A C10A 124.5(4) . . ?
N2A C9A H9A 117.8 . . ?
C10A C9A H9A 117.8 . . ?
C9A C10A C6A 119.3(4) . . ?
C9A C10A H10A 120.4 . . ?
C6A C10A H10A 120.4 . . ?
N1A C11A C12A 110.7(3) . . ?
N1A C11A H11C 109.5 . . ?
C12A C11A H11C 109.5 . . ?
N1A C11A H11D 109.5 . . ?
C12A C11A H11D 109.5 . . ?
H11C C11A H11D 108.1 . . ?
C17A C12A C13A 115.9(4) . . ?
C17A C12A C11A 120.5(4) . . ?
C13A C12A C11A 123.5(4) . . ?
F13A C13A C14A 119.1(4) . . ?
F13A C13A C12A 118.6(4) . . ?
C14A C13A C12A 122.3(4) . . ?
F14A C14A C13A 120.5(4) . . ?
F14A C14A C15A 120.1(4) . . ?
C13A C14A C15A 119.4(4) . . ?
F15A C15A C16A 120.8(4) . . ?
F15A C15A C14A 119.6(4) . . ?
C16A C15A C14A 119.6(4) . . ?
F16A C16A C17A 120.6(4) . . ?
F16A C16A C15A 119.8(4) . . ?
C17A C16A C15A 119.6(4) . . ?
F17A C17A C16A 118.4(4) . . ?
F17A C17A C12A 118.4(4) . . ?
C16A C17A C12A 123.2(4) . . ?
H1H O1B H1I 106(3) . . ?
C1B N1B C5B 120.5(3) . . ?
C1B N1B C11B 120.5(3) . . ?
C5B N1B C11B 118.9(3) . . ?
C8B N2B C9B 116.6(3) . . ?
N1B C1B C2B 120.6(4) . . ?
N1B C1B H1B 119.7 . . ?
C2B C1B H1B 119.7 . . ?
C1B C2B C3B 120.3(3) . . ?
C1B C2B H2B 119.9 . . ?
C3B C2B H2B 119.9 . . ?
C2B C3B C4B 117.5(3) . . ?
C2B C3B C6B 121.2(3) . . ?
C4B C3B C6B 121.3(3) . . ?
C5B C4B C3B 120.2(4) . . ?
C5B C4B H4B 119.9 . . ?
C3B C4B H4B 119.9 . . ?
N1B C5B C4B 120.6(3) . . ?
N1B C5B H5B 119.7 . . ?
C4B C5B H5B 119.7 . . ?
C10B C6B C7B 116.9(4) . . ?
C10B C6B C3B 120.5(3) . . ?
C7B C6B C3B 122.5(3) . . ?
C8B C7B C6B 119.1(4) . . ?
C8B C7B H7B 120.4 . . ?
C6B C7B H7B 120.4 . . ?
N2B C8B C7B 124.5(4) . . ?
N2B C8B H8B 117.8 . . ?
C7B C8B H8B 117.8 . . ?
N2B C9B C10B 123.1(4) . . ?
N2B C9B H9B 118.4 . . ?
C10B C9B H9B 118.4 . . ?
C6B C10B C9B 119.8(4) . . ?
C6B C10B H10B 120.1 . . ?
C9B C10B H10B 120.1 . . ?
N1B C11B C12B 113.4(3) . . ?
N1B C11B H11E 108.9 . . ?
C12B C11B H11E 108.9 . . ?
N1B C11B H11F 108.9 . . ?
C12B C11B H11F 108.9 . . ?
H11E C11B H11F 107.7 . . ?
C17B C12B C13B 116.9(4) . . ?
C17B C12B C11B 120.3(3) . . ?
C13B C12B C11B 122.8(3) . . ?
F13B C13B C14B 119.1(4) . . ?
F13B C13B C12B 119.5(4) . . ?
C14B C13B C12B 121.4(4) . . ?
F14B C14B C13B 120.3(4) . . ?
F14B C14B C15B 119.9(4) . . ?
C13B C14B C15B 119.8(4) . . ?
F15B C15B C16B 120.7(4) . . ?
F15B C15B C14B 119.5(4) . . ?
C16B C15B C14B 119.8(4) . . ?
F16B C16B C17B 120.2(4) . . ?
F16B C16B C15B 120.4(4) . . ?
C17B C16B C15B 119.5(4) . . ?
F17B C17B C16B 118.9(3) . . ?
F17B C17B C12B 118.5(3) . . ?
C16B C17B C12B 122.6(4) . . ?
H1J O1C H1K 108(3) . . ?
C5C N1C C1C 120.3(3) . . ?
C5C N1C C11C 120.4(3) . . ?
C1C N1C C11C 119.2(3) . . ?
C8C N2C C9C 115.6(3) . . ?
N1C C1C C2C 120.2(3) . . ?
N1C C1C H1C 119.9 . . ?
C2C C1C H1C 119.9 . . ?
C1C C2C C3C 120.9(3) . . ?
C1C C2C H2C 119.6 . . ?
C3C C2C H2C 119.6 . . ?
C4C C3C C2C 116.8(3) . . ?
C4C C3C C6C 121.1(3) . . ?
C2C C3C C6C 122.1(3) . . ?
C5C C4C C3C 120.4(4) . . ?
C5C C4C H4C 119.8 . . ?
C3C C4C H4C 119.8 . . ?
N1C C5C C4C 121.5(3) . . ?
N1C C5C H5C 119.3 . . ?
C4C C5C H5C 119.3 . . ?
C10C C6C C7C 116.9(3) . . ?
C10C C6C C3C 121.7(3) . . ?
C7C C6C C3C 121.4(3) . . ?
C8C C7C C6C 119.6(4) . . ?
C8C C7C H7C 120.2 . . ?
C6C C7C H7C 120.2 . . ?
N2C C8C C7C 124.3(4) . . ?
N2C C8C H8C 117.8 . . ?
C7C C8C H8C 117.8 . . ?
N2C C9C C10C 124.2(4) . . ?
N2C C9C H9C 117.9 . . ?
C10C C9C H9C 117.9 . . ?
C9C C10C C6C 119.3(4) . . ?
C9C C10C H10C 120.3 . . ?
C6C C10C H10C 120.3 . . ?
N1C C11C C12C 111.2(3) . . ?
N1C C11C H11G 109.4 . . ?
C12C C11C H11G 109.4 . . ?
N1C C11C H11H 109.4 . . ?
C12C C11C H11H 109.4 . . ?
H11G C11C H11H 108.0 . . ?
C17C C12C C13C 116.4(3) . . ?
C17C C12C C11C 122.4(3) . . ?
C13C C12C C11C 121.1(3) . . ?
F13C C13C C14C 118.6(3) . . ?
F13C C13C C12C 118.8(3) . . ?
C14C C13C C12C 122.6(3) . . ?
F14C C14C C13C 121.4(3) . . ?
F14C C14C C15C 119.3(3) . . ?
C13C C14C C15C 119.2(4) . . ?
F15C C15C C14C 120.7(4) . . ?
F15C C15C C16C 119.4(4) . . ?
C14C C15C C16C 119.9(4) . . ?
F16C C16C C15C 120.0(3) . . ?
F16C C16C C17C 120.4(4) . . ?
C15C C16C C17C 119.7(4) . . ?
F17C C17C C12C 119.7(3) . . ?
F17C C17C C16C 118.1(3) . . ?
C12C C17C C16C 122.2(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.4(5) . . . . ?
C11 N1 C1 C2 -176.8(3) . . . . ?
N1 C1 C2 C3 0.5(6) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C1 C2 C3 C6 179.9(3) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C6 C3 C4 C5 179.9(3) . . . . ?
C1 N1 C5 C4 0.1(5) . . . . ?
C11 N1 C5 C4 176.5(3) . . . . ?
C3 C4 C5 N1 0.0(6) . . . . ?
C4 C3 C6 C7 171.3(4) . . . . ?
C2 C3 C6 C7 -8.9(5) . . . . ?
C4 C3 C6 C10 -9.5(5) . . . . ?
C2 C3 C6 C10 170.3(3) . . . . ?
C10 C6 C7 C8 0.2(6) . . . . ?
C3 C6 C7 C8 179.4(3) . . . . ?
C9 N2 C8 C7 -0.9(6) . . . . ?
C6 C7 C8 N2 0.6(6) . . . . ?
C8 N2 C9 C10 0.4(6) . . . . ?
N2 C9 C10 C6 0.3(6) . . . . ?
C7 C6 C10 C9 -0.6(6) . . . . ?
C3 C6 C10 C9 -179.8(3) . . . . ?
C1 N1 C11 C12 -63.5(4) . . . . ?
C5 N1 C11 C12 120.2(4) . . . . ?
N1 C11 C12 C17 111.6(4) . . . . ?
N1 C11 C12 C13 -70.1(4) . . . . ?
C17 C12 C13 F13 179.8(3) . . . . ?
C11 C12 C13 F13 1.5(5) . . . . ?
C17 C12 C13 C14 -1.2(5) . . . . ?
C11 C12 C13 C14 -179.5(3) . . . . ?
F13 C13 C14 F14 1.7(5) . . . . ?
C12 C13 C14 F14 -177.3(3) . . . . ?
F13 C13 C14 C15 179.4(3) . . . . ?
C12 C13 C14 C15 0.4(6) . . . . ?
F14 C14 C15 F15 0.6(5) . . . . ?
C13 C14 C15 F15 -177.1(3) . . . . ?
F14 C14 C15 C16 178.7(3) . . . . ?
C13 C14 C15 C16 1.0(5) . . . . ?
F15 C15 C16 F16 -3.4(5) . . . . ?
C14 C15 C16 F16 178.6(3) . . . . ?
F15 C15 C16 C17 176.6(3) . . . . ?
C14 C15 C16 C17 -1.4(6) . . . . ?
F16 C16 C17 F17 0.6(5) . . . . ?
C15 C16 C17 F17 -179.4(3) . . . . ?
F16 C16 C17 C12 -179.4(3) . . . . ?
C15 C16 C17 C12 0.6(6) . . . . ?
C13 C12 C17 F17 -179.4(3) . . . . ?
C11 C12 C17 F17 -1.1(5) . . . . ?
C13 C12 C17 C16 0.7(6) . . . . ?
C11 C12 C17 C16 179.0(4) . . . . ?
C5A N1A C1A C2A 2.0(6) . . . . ?
C11A N1A C1A C2A -179.0(3) . . . . ?
N1A C1A C2A C3A 0.4(6) . . . . ?
C1A C2A C3A C4A -3.1(5) . . . . ?
C1A C2A C3A C6A 175.5(4) . . . . ?
C2A C3A C4A C5A 3.7(6) . . . . ?
C6A C3A C4A C5A -174.9(4) . . . . ?
C1A N1A C5A C4A -1.4(6) . . . . ?
C11A N1A C5A C4A 179.6(4) . . . . ?
C3A C4A C5A N1A -1.5(6) . . . . ?
C2A C3A C6A C7A -5.3(6) . . . . ?
C4A C3A C6A C7A 173.2(4) . . . . ?
C2A C3A C6A C10A 175.2(4) . . . . ?
C4A C3A C6A C10A -6.2(6) . . . . ?
C10A C6A C7A C8A 2.2(6) . . . . ?
C3A C6A C7A C8A -177.3(4) . . . . ?
C9A N2A C8A C7A -1.0(6) . . . . ?
C6A C7A C8A N2A -0.3(7) . . . . ?
C8A N2A C9A C10A 0.4(7) . . . . ?
N2A C9A C10A C6A 1.5(7) . . . . ?
C7A C6A C10A C9A -2.7(6) . . . . ?
C3A C6A C10A C9A 176.8(4) . . . . ?
C5A N1A C11A C12A 76.6(4) . . . . ?
C1A N1A C11A C12A -102.4(4) . . . . ?
N1A C11A C12A C17A 74.8(4) . . . . ?
N1A C11A C12A C13A -101.5(4) . . . . ?
C17A C12A C13A F13A 179.5(3) . . . . ?
C11A C12A C13A F13A -4.0(6) . . . . ?
C17A C12A C13A C14A 0.5(6) . . . . ?
C11A C12A C13A C14A 177.0(4) . . . . ?
F13A C13A C14A F14A 1.5(6) . . . . ?
C12A C13A C14A F14A -179.5(4) . . . . ?
F13A C13A C14A C15A -179.1(4) . . . . ?
C12A C13A C14A C15A -0.1(7) . . . . ?
F14A C14A C15A F15A 0.5(6) . . . . ?
C13A C14A C15A F15A -178.9(4) . . . . ?
F14A C14A C15A C16A 179.0(4) . . . . ?
C13A C14A C15A C16A -0.4(6) . . . . ?
F15A C15A C16A F16A 1.2(6) . . . . ?
C14A C15A C16A F16A -177.3(4) . . . . ?
F15A C15A C16A C17A 178.9(4) . . . . ?
C14A C15A C16A C17A 0.5(6) . . . . ?
F16A C16A C17A F17A -0.8(6) . . . . ?
C15A C16A C17A F17A -178.6(4) . . . . ?
F16A C16A C17A C12A 177.7(3) . . . . ?
C15A C16A C17A C12A 0.0(6) . . . . ?
C13A C12A C17A F17A 178.1(3) . . . . ?
C11A C12A C17A F17A 1.5(5) . . . . ?
C13A C12A C17A C16A -0.5(6) . . . . ?
C11A C12A C17A C16A -177.0(4) . . . . ?
C5B N1B C1B C2B 4.2(5) . . . . ?
C11B N1B C1B C2B -171.2(3) . . . . ?
N1B C1B C2B C3B 0.5(6) . . . . ?
C1B C2B C3B C4B -5.4(6) . . . . ?
C1B C2B C3B C6B 172.4(4) . . . . ?
C2B C3B C4B C5B 5.9(6) . . . . ?
C6B C3B C4B C5B -171.9(4) . . . . ?
C1B N1B C5B C4B -3.7(5) . . . . ?
C11B N1B C5B C4B 171.8(3) . . . . ?
C3B C4B C5B N1B -1.5(6) . . . . ?
C2B C3B C6B C10B -150.7(4) . . . . ?
C4B C3B C6B C10B 27.0(5) . . . . ?
C2B C3B C6B C7B 26.1(6) . . . . ?
C4B C3B C6B C7B -156.1(4) . . . . ?
C10B C6B C7B C8B -1.8(5) . . . . ?
C3B C6B C7B C8B -178.8(4) . . . . ?
C9B N2B C8B C7B -0.7(6) . . . . ?
C6B C7B C8B N2B 2.1(6) . . . . ?
C8B N2B C9B C10B -0.9(6) . . . . ?
C7B C6B C10B C9B 0.4(6) . . . . ?
C3B C6B C10B C9B 177.4(4) . . . . ?
N2B C9B C10B C6B 1.0(6) . . . . ?
C1B N1B C11B C12B -107.4(4) . . . . ?
C5B N1B C11B C12B 77.2(4) . . . . ?
N1B C11B C12B C17B 71.0(5) . . . . ?
N1B C11B C12B C13B -110.2(4) . . . . ?
C17B C12B C13B F13B 179.3(3) . . . . ?
C11B C12B C13B F13B 0.5(6) . . . . ?
C17B C12B C13B C14B 1.3(6) . . . . ?
C11B C12B C13B C14B -177.5(4) . . . . ?
F13B C13B C14B F14B 1.8(6) . . . . ?
C12B C13B C14B F14B 179.8(4) . . . . ?
F13B C13B C14B C15B -178.6(4) . . . . ?
C12B C13B C14B C15B -0.6(6) . . . . ?
F14B C14B C15B F15B -1.0(6) . . . . ?
C13B C14B C15B F15B 179.4(4) . . . . ?
F14B C14B C15B C16B 179.4(4) . . . . ?
C13B C14B C15B C16B -0.2(6) . . . . ?
F15B C15B C16B F16B 1.9(6) . . . . ?
C14B C15B C16B F16B -178.5(4) . . . . ?
F15B C15B C16B C17B -179.3(4) . . . . ?
C14B C15B C16B C17B 0.3(6) . . . . ?
F16B C16B C17B F17B -1.1(6) . . . . ?
C15B C16B C17B F17B -179.8(4) . . . . ?
F16B C16B C17B C12B 179.2(3) . . . . ?
C15B C16B C17B C12B 0.5(6) . . . . ?
C13B C12B C17B F17B 179.1(3) . . . . ?
C11B C12B C17B F17B -2.1(5) . . . . ?
C13B C12B C17B C16B -1.2(6) . . . . ?
C11B C12B C17B C16B 177.6(4) . . . . ?
C5C N1C C1C C2C -0.6(5) . . . . ?
C11C N1C C1C C2C -177.2(3) . . . . ?
N1C C1C C2C C3C 0.6(5) . . . . ?
C1C C2C C3C C4C -0.9(5) . . . . ?
C1C C2C C3C C6C 179.8(3) . . . . ?
C2C C3C C4C C5C 1.2(5) . . . . ?
C6C C3C C4C C5C -179.4(3) . . . . ?
C1C N1C C5C C4C 0.9(5) . . . . ?
C11C N1C C5C C4C 177.5(3) . . . . ?
C3C C4C C5C N1C -1.2(6) . . . . ?
C4C C3C C6C C10C -3.0(5) . . . . ?
C2C C3C C6C C10C 176.4(4) . . . . ?
C4C C3C C6C C7C 177.1(4) . . . . ?
C2C C3C C6C C7C -3.5(6) . . . . ?
C10C C6C C7C C8C 1.0(6) . . . . ?
C3C C6C C7C C8C -179.0(4) . . . . ?
C9C N2C C8C C7C -0.6(6) . . . . ?
C6C C7C C8C N2C -0.5(6) . . . . ?
C8C N2C C9C C10C 1.3(6) . . . . ?
N2C C9C C10C C6C -0.8(6) . . . . ?
C7C C6C C10C C9C -0.4(6) . . . . ?
C3C C6C C10C C9C 179.6(3) . . . . ?
C5C N1C C11C C12C 116.5(4) . . . . ?
C1C N1C C11C C12C -66.8(4) . . . . ?
N1C C11C C12C C17C 106.5(4) . . . . ?
N1C C11C C12C C13C -75.7(4) . . . . ?
C17C C12C C13C F13C 180.0(3) . . . . ?
C11C C12C C13C F13C 2.1(5) . . . . ?
C17C C12C C13C C14C -1.0(5) . . . . ?
C11C C12C C13C C14C -178.9(3) . . . . ?
F13C C13C C14C F14C 1.0(5) . . . . ?
C12C C13C C14C F14C -178.1(3) . . . . ?
F13C C13C C14C C15C 178.8(3) . . . . ?
C12C C13C C14C C15C -0.3(6) . . . . ?
F14C C14C C15C F15C 1.6(5) . . . . ?
C13C C14C C15C F15C -176.2(3) . . . . ?
F14C C14C C15C C16C 179.6(3) . . . . ?
C13C C14C C15C C16C 1.7(6) . . . . ?
F15C C15C C16C F16C -2.1(5) . . . . ?
C14C C15C C16C F16C 179.9(3) . . . . ?
F15C C15C C16C C17C 176.1(3) . . . . ?
C14C C15C C16C C17C -1.9(6) . . . . ?
C13C C12C C17C F17C -179.7(3) . . . . ?
C11C C12C C17C F17C -1.8(5) . . . . ?
C13C C12C C17C C16C 0.8(5) . . . . ?
C11C C12C C17C C16C 178.7(3) . . . . ?
F16C C16C C17C F17C -0.8(5) . . . . ?
C15C C16C C17C F17C -178.9(3) . . . . ?
F16C C16C C17C C12C 178.8(3) . . . . ?
C15C C16C C17C C12C 0.6(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1D Br1 0.85(2) 2.53(2) 3.371(3) 172(4) .
O1 H1E Br1C 0.84(2) 2.52(2) 3.352(3) 171(4) 2_766
O1A H1F Br1B 0.85(2) 2.54(2) 3.389(3) 176(5) 2_767
O1A H1G Br1A 0.85(2) 2.54(2) 3.374(3) 172(4) .
O1B H1H Br1A 0.84(2) 2.55(2) 3.381(3) 173(5) 2_767
O1B H1I Br1B 0.84(2) 2.65(2) 3.466(3) 165(4) .
O1C H1J Br1 0.84(2) 2.499(19) 3.335(3) 178(5) 2_766
O1C H1K Br1C 0.84(2) 2.54(2) 3.341(3) 162(4) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.087

_iucr_refine_instructions_details 
;
TITL mm-bipy-1 in P -1
CELL   0.71073  13.6652  14.6348  18.0643  77.611  73.769  75.674
ZERR     8       0.0003   0.0003   0.0003   0.002   0.002   0.002
LATT  1
SFAC        C       H       N       O       F       BR
UNIT       136      96      16      8       40      8
L.S.      10
OMIT -3 50.5
OMIT 0 0 2
OMIT -12 2 5
OMIT -4 8 14
TEMP  -150
SIZE  0.15 0.13 0.10
EQIV $1 -x+2, -y+1, -z+1
EQIV $2 -x+2, -y+1, -z+2
HTAB O1 Br1
HTAB O1 Br1C_$1
HTAB O1A Br1B_$2
HTAB O1A Br1A
HTAB O1B Br1A_$2
HTAB O1B Br1B
HTAB O1C Br1_$1
HTAB O1C Br1C
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.000000    5.153200
FVAR       0.26009
MOLE 1
BR1   6    0.846017    0.323752    0.595156    11.00000    0.02575    0.02699 =
         0.02736   -0.00635   -0.00163   -0.00740
F13   5    0.634300    0.183016    0.757158    11.00000    0.03513    0.02929 =
         0.02626   -0.00018   -0.01612   -0.00042
F14   5    0.560428    0.373876    0.735445    11.00000    0.04206    0.02670 =
         0.03554   -0.01344   -0.01378    0.00121
F15   5    0.527023    0.464677    0.594263    11.00000    0.02632    0.01878 =
         0.04570   -0.00004   -0.01365   -0.00101
F16   5    0.561060    0.363355    0.477233    11.00000    0.05228    0.03646 =
         0.03102    0.00503   -0.02047   -0.00627
F17   5    0.639265    0.174234    0.497057    11.00000    0.05028    0.03760 =
         0.02961   -0.01036   -0.01366   -0.00701
O1    4    0.901551    0.223143    0.433114    11.00000    0.03619    0.04511 =
         0.02214   -0.00078   -0.00665   -0.01074
H1D   2    0.886880    0.254122    0.470763    11.00000   -1.50000
H1E   2    0.966917    0.205942    0.422999    11.00000   -1.50000
N1    3    0.789273    0.046111    0.651675    11.00000    0.01964    0.01577 =
         0.02585   -0.00393   -0.00459   -0.00285
N2    3    1.306807   -0.080998    0.695367    11.00000    0.03182    0.02471 =
         0.03986   -0.00490   -0.01231   -0.00454
C1    1    0.866329    0.073344    0.592673    11.00000    0.02330    0.01973 =
         0.02281    0.00014   -0.00465   -0.00642
AFIX  43
H1    2    0.850223    0.109435    0.545682    11.00000   -1.20000
AFIX   0
C2    1    0.968101    0.050275    0.598565    11.00000    0.02306    0.02328 =
         0.02277   -0.00358   -0.00293   -0.00728
AFIX  43
H2    2    1.021302    0.070777    0.556208    11.00000   -1.20000
AFIX   0
C3    1    0.992832   -0.003652    0.667429    11.00000    0.02323    0.01632 =
         0.02357   -0.00688   -0.00675   -0.00364
C4    1    0.910510   -0.030804    0.727396    11.00000    0.02517    0.02296 =
         0.01980    0.00260   -0.00319   -0.00507
AFIX  43
H4    2    0.924010   -0.067322    0.775023    11.00000   -1.20000
AFIX   0
C5    1    0.810523   -0.005423    0.718380    11.00000    0.02374    0.01979 =
         0.02554   -0.00199   -0.00213   -0.00560
AFIX  43
H5    2    0.755584   -0.024533    0.759841    11.00000   -1.20000
AFIX   0
C6    1    1.101603   -0.030284    0.676188    11.00000    0.02698    0.01207 =
         0.02533   -0.00359   -0.00763   -0.00298
C7    1    1.185581   -0.015132    0.614519    11.00000    0.02584    0.02661 =
         0.02528   -0.00473   -0.00575   -0.00674
AFIX  43
H7    2    1.174945    0.012762    0.564097    11.00000   -1.20000
AFIX   0
C8    1    1.284904   -0.040641    0.626415    11.00000    0.02261    0.03117 =
         0.03662   -0.00620   -0.00309   -0.00977
AFIX  43
H8    2    1.341082   -0.028879    0.583126    11.00000   -1.20000
AFIX   0
C9    1    1.225821   -0.095186    0.754905    11.00000    0.02901    0.02830 =
         0.03197    0.00093   -0.01446   -0.00354
AFIX  43
H9    2    1.238955   -0.123299    0.804604    11.00000   -1.20000
AFIX   0
C10   1    1.123980   -0.071361    0.748460    11.00000    0.02651    0.02307 =
         0.02880   -0.00386   -0.00557   -0.00141
AFIX  43
H10   2    1.069255   -0.082837    0.792994    11.00000   -1.20000
AFIX   0
C11   1    0.680988    0.067942    0.641675    11.00000    0.01780    0.02235 =
         0.03285   -0.00031   -0.00842   -0.00757
AFIX  23
H11A  2    0.635599    0.038461    0.689031    11.00000   -1.20000
H11B  2    0.679638    0.039753    0.596898    11.00000   -1.20000
AFIX   0
C12   1    0.639571    0.173504    0.627861    11.00000    0.01495    0.02273 =
         0.02898   -0.00432   -0.00406   -0.00577
C13   1    0.616446    0.227385    0.687186    11.00000    0.01562    0.02328 =
         0.02442    0.00091   -0.00656   -0.00320
C14   1    0.577818    0.323804    0.677610    11.00000    0.01768    0.02254 =
         0.02721   -0.00945   -0.00452   -0.00196
C15   1    0.560664    0.369026    0.606290    11.00000    0.01752    0.01875 =
         0.03509    0.00072   -0.01024   -0.00348
C16   1    0.580308    0.318492    0.545901    11.00000    0.02410    0.03033 =
         0.02603    0.00386   -0.01079   -0.00536
C17   1    0.619643    0.222181    0.558013    11.00000    0.02303    0.02793 =
         0.02144   -0.00644   -0.00376   -0.00536
MOLE 2
BR1A  6    0.905931    0.378486    0.919609    11.00000    0.03051    0.02630 =
         0.02680    0.00122   -0.01067   -0.00365
F13A  5    0.703513    0.102781    1.046400    11.00000    0.04397    0.03568 =
         0.03896    0.01205   -0.00842   -0.01229
F14A  5    0.603389    0.246213    1.129805    11.00000    0.04925    0.07227 =
         0.02990   -0.00293    0.00278   -0.00598
F15A  5    0.564000    0.428450    1.055518    11.00000    0.04286    0.05432 =
         0.05333   -0.02320   -0.00535    0.00762
F16A  5    0.629166    0.468337    0.896993    11.00000    0.03819    0.02574 =
         0.05502   -0.00116   -0.00997    0.00213
F17A  5    0.729118    0.325219    0.815188    11.00000    0.03361    0.02809 =
         0.03113    0.00613   -0.00886   -0.00555
O1A   4    0.884618    0.191849    1.065789    11.00000    0.03695    0.05280 =
         0.04003    0.01095   -0.00991   -0.01436
H1F   2    0.948346    0.171284    1.065876    11.00000   -1.50000
H1G   2    0.883207    0.241340    1.031602    11.00000   -1.50000
N1A   3    0.891260    0.138981    0.855697    11.00000    0.02391    0.01861 =
         0.02471   -0.00207   -0.00729   -0.00643
N2A   3    1.432715    0.123582    0.744644    11.00000    0.02866    0.03631 =
         0.03080   -0.00741   -0.00363   -0.00457
C1A   1    0.934108    0.177803    0.782844    11.00000    0.03099    0.02776 =
         0.01980   -0.00246   -0.01029   -0.00249
AFIX  43
H1A   2    0.892174    0.203387    0.746341    11.00000   -1.20000
AFIX   0
C2A   1    1.037886    0.180646    0.761003    11.00000    0.02976    0.02384 =
         0.01837   -0.00071   -0.00510   -0.00380
AFIX  43
H2A   2    1.066879    0.208617    0.709440    11.00000   -1.20000
AFIX   0
C3A   1    1.101679    0.143327    0.812925    11.00000    0.02872    0.01642 =
         0.02052   -0.00701   -0.00717   -0.00111
C4A   1    1.052267    0.107465    0.889434    11.00000    0.02918    0.02904 =
         0.02465   -0.00261   -0.01233   -0.00395
AFIX  43
H4A   2    1.091333    0.084655    0.928029    11.00000   -1.20000
AFIX   0
C5A   1    0.948935    0.105138    0.908700    11.00000    0.02920    0.03173 =
         0.02276    0.00169   -0.00814   -0.00908
AFIX  43
H5A   2    0.917278    0.079260    0.960258    11.00000   -1.20000
AFIX   0
C6A   1    1.215279    0.139069    0.789517    11.00000    0.02867    0.01765 =
         0.02157   -0.00352   -0.00701   -0.00319
C7A   1    1.266550    0.164963    0.712695    11.00000    0.03085    0.03731 =
         0.02079   -0.00326   -0.00755   -0.00795
AFIX  43
H7A   2    1.228647    0.188807    0.673443    11.00000   -1.20000
AFIX   0
C8A   1    1.373387    0.155709    0.693850    11.00000    0.02855    0.04115 =
         0.02330   -0.00581    0.00194   -0.01174
AFIX  43
H8A   2    1.406742    0.173607    0.640779    11.00000   -1.20000
AFIX   0
C9A   1    1.382567    0.100754    0.818477    11.00000    0.02916    0.04888 =
         0.03013    0.00389   -0.01148   -0.00410
AFIX  43
H9A   2    1.422706    0.077927    0.856384    11.00000   -1.20000
AFIX   0
C10A  1    1.276215    0.107979    0.843741    11.00000    0.03002    0.04789 =
         0.01833    0.00481   -0.00325   -0.00845
AFIX  43
H10A  2    1.244952    0.091903    0.897561    11.00000   -1.20000
AFIX   0
C11A  1    0.779272    0.133916    0.880031    11.00000    0.02309    0.02713 =
         0.03170    0.00029   -0.01221   -0.00491
AFIX  23
H11C  2    0.771057    0.070428    0.910812    11.00000   -1.20000
H11D  2    0.752105    0.141903    0.833161    11.00000   -1.20000
AFIX   0
C12A  1    0.718006    0.210264    0.928245    11.00000    0.01904    0.02532 =
         0.02984    0.00594   -0.00966   -0.00664
C13A  1    0.685078    0.193387    1.009037    11.00000    0.02049    0.03448 =
         0.03505    0.00812   -0.00872   -0.00854
C14A  1    0.633283    0.265232    1.051842    11.00000    0.02881    0.04825 =
         0.02379   -0.00249   -0.00008   -0.00876
C15A  1    0.612881    0.358041    1.013897    11.00000    0.02113    0.03877 =
         0.04849   -0.01503   -0.00437   -0.00125
C16A  1    0.645222    0.377023    0.934068    11.00000    0.02715    0.02440 =
         0.03910    0.00192   -0.01289   -0.00250
C17A  1    0.696168    0.304425    0.893332    11.00000    0.01709    0.03167 =
         0.02761    0.00342   -0.00395   -0.00618
MOLE 3
BR1B  6    0.859621    0.877481    0.934255    11.00000    0.03646    0.02936 =
         0.02392    0.00052   -0.01166   -0.00695
F13B  5    0.680197    0.581271    1.027441    11.00000    0.04633    0.03371 =
         0.03647    0.01376   -0.01252   -0.01520
F14B  5    0.540703    0.712258    1.108786    11.00000    0.04713    0.07010 =
         0.02922   -0.00764    0.00434   -0.02244
F15B  5    0.489428    0.894178    1.037571    11.00000    0.03584    0.05535 =
         0.06073   -0.03684   -0.00012    0.00264
F16B  5    0.585087    0.947207    0.884823    11.00000    0.04998    0.02410 =
         0.05663   -0.00752   -0.01790    0.00629
F17B  5    0.724483    0.815870    0.805055    11.00000    0.03516    0.02474 =
         0.02654    0.00474   -0.00607   -0.00810
O1B   4    0.842443    0.671889    1.070441    11.00000    0.03509    0.05118 =
         0.03237    0.00119   -0.00839   -0.00822
H1H   2    0.903241    0.663138    1.075693    11.00000   -1.50000
H1I   2    0.836262    0.719508    1.035222    11.00000   -1.50000
N1B   3    0.890189    0.639431    0.845268    11.00000    0.02226    0.02000 =
         0.02047   -0.00319   -0.00665   -0.00139
N2B   3    1.431641    0.606549    0.731278    11.00000    0.02234    0.03260 =
         0.02742   -0.00858   -0.00352   -0.00422
C1B   1    0.934511    0.674648    0.771444    11.00000    0.02743    0.02203 =
         0.02124   -0.00321   -0.00775   -0.00126
AFIX  43
H1B   2    0.893256    0.698328    0.734322    11.00000   -1.20000
AFIX   0
C2B   1    1.037994    0.676577    0.749600    11.00000    0.02297    0.02768 =
         0.01725   -0.00199   -0.00212   -0.00457
AFIX  43
H2B   2    1.068261    0.702013    0.697543    11.00000   -1.20000
AFIX   0
C3B   1    1.099499    0.641405    0.803299    11.00000    0.02088    0.02165 =
         0.02220   -0.00561   -0.00698   -0.00336
C4B   1    1.049674    0.612529    0.880546    11.00000    0.02253    0.02807 =
         0.02052   -0.00173   -0.00746   -0.00538
AFIX  43
H4B   2    1.087981    0.593848    0.919711    11.00000   -1.20000
AFIX   0
C5B   1    0.946088    0.611059    0.899962    11.00000    0.02337    0.02641 =
         0.02053   -0.00225   -0.00523   -0.00594
AFIX  43
H5B   2    0.913031    0.589879    0.952435    11.00000   -1.20000
AFIX   0
C6B   1    1.213646    0.631817    0.778765    11.00000    0.02369    0.02116 =
         0.02117   -0.00784   -0.00639   -0.00239
C7B   1    1.262518    0.688105    0.713403    11.00000    0.02410    0.02530 =
         0.02787   -0.00485   -0.00697   -0.00242
AFIX  43
H7B   2    1.222643    0.735886    0.682948    11.00000   -1.20000
AFIX   0
C8B   1    1.369547    0.673690    0.693367    11.00000    0.03107    0.03141 =
         0.02660   -0.00478   -0.00170   -0.01326
AFIX  43
H8B   2    1.401264    0.714369    0.649549    11.00000   -1.20000
AFIX   0
C9B   1    1.385129    0.551084    0.793058    11.00000    0.02187    0.03425 =
         0.02977   -0.00394   -0.00684   -0.00011
AFIX  43
H9B   2    1.427426    0.502025    0.820780    11.00000   -1.20000
AFIX   0
C10B  1    1.277537    0.561657    0.818857    11.00000    0.02343    0.03252 =
         0.02422   -0.00092   -0.00383   -0.00423
AFIX  43
H10B  2    1.247893    0.521063    0.863705    11.00000   -1.20000
AFIX   0
C11B  1    0.781395    0.624469    0.866234    11.00000    0.01768    0.02154 =
         0.03692   -0.00321   -0.00956   -0.00500
AFIX  23
H11E  2    0.779329    0.559448    0.895951    11.00000   -1.20000
H11F  2    0.759373    0.628344    0.817702    11.00000   -1.20000
AFIX   0
C12B  1    0.705471    0.695766    0.914020    11.00000    0.01633    0.02339 =
         0.02469    0.00193   -0.00681   -0.00631
C13B  1    0.657923    0.671611    0.991934    11.00000    0.02165    0.03132 =
         0.02848    0.00263   -0.00872   -0.00913
C14B  1    0.585980    0.737561    1.033204    11.00000    0.02630    0.05218 =
         0.02286   -0.00818    0.00130   -0.01708
C15B  1    0.560567    0.830328    0.997055    11.00000    0.02424    0.04127 =
         0.04055   -0.01581   -0.00632   -0.00161
C16B  1    0.607521    0.856148    0.920327    11.00000    0.02953    0.01998 =
         0.03889   -0.00384   -0.01330   -0.00199
C17B  1    0.678699    0.789542    0.880382    11.00000    0.02457    0.02363 =
         0.02390   -0.00201   -0.00666   -0.00553
MOLE 4
BR1C  6    0.840092    0.834467    0.588003    11.00000    0.02616    0.02707 =
         0.02982   -0.00836   -0.00283   -0.00671
F13C  5    0.618005    0.671168    0.762576    11.00000    0.03425    0.02974 =
         0.02505    0.00133   -0.01456   -0.00376
F14C  5    0.538048    0.861249    0.756309    11.00000    0.03640    0.03358 =
         0.04146   -0.01529   -0.01676    0.00224
F15C  5    0.517895    0.970623    0.617862    11.00000    0.02895    0.01953 =
         0.05324    0.00068   -0.01820   -0.00265
F16C  5    0.567934    0.889772    0.487652    11.00000    0.04429    0.03523 =
         0.03153    0.01489   -0.01532   -0.00691
F17C  5    0.648042    0.701741    0.492409    11.00000    0.03851    0.04311 =
         0.02305   -0.00641   -0.00412   -0.00668
O1C   4    0.897104    0.738344    0.425454    11.00000    0.03193    0.04518 =
         0.02547   -0.00546   -0.00593   -0.00810
H1J   2    0.961689    0.723362    0.419181    11.00000   -1.50000
H1K   2    0.873662    0.772891    0.460421    11.00000   -1.50000
DFIX 0.84 O1 H1D O1 H1E O1A H1F O1A H1G O1B H1H O1B H1I O1C H1J O1C H1K
DFIX 1.35 H1D H1E H1F H1G H1H H1I H1J H1K
N1C   3    0.788134    0.552024    0.640283    11.00000    0.01656    0.01600 =
         0.02303   -0.00068   -0.00312   -0.00407
N2C   3    1.312541    0.418290    0.670815    11.00000    0.02488    0.03129 =
         0.04107   -0.00493   -0.00995   -0.00321
C1C   1    0.863542    0.582862    0.580394    11.00000    0.02424    0.01904 =
         0.01807   -0.00080   -0.00510   -0.00600
AFIX  43
H1C   2    0.845914    0.621543    0.534718    11.00000   -1.20000
AFIX   0
C2C   1    0.965539    0.558364    0.585487    11.00000    0.02299    0.02043 =
         0.02126   -0.00026   -0.00375   -0.00594
AFIX  43
H2C   2    1.017794    0.580837    0.543346    11.00000   -1.20000
AFIX   0
C3C   1    0.993408    0.500793    0.651886    11.00000    0.02298    0.01575 =
         0.02140   -0.00430   -0.00642   -0.00277
C4C   1    0.912852    0.471140    0.712277    11.00000    0.02001    0.02270 =
         0.02203   -0.00005   -0.00478   -0.00634
AFIX  43
H4C   2    0.927892    0.432944    0.758920    11.00000   -1.20000
AFIX   0
C5C   1    0.812487    0.496782    0.704631    11.00000    0.02149    0.02166 =
         0.01975   -0.00290    0.00148   -0.00566
AFIX  43
H5C   2    0.758847    0.474948    0.745849    11.00000   -1.20000
AFIX   0
C6C   1    1.103698    0.472658    0.658986    11.00000    0.02310    0.01612 =
         0.02583   -0.00480   -0.00551   -0.00299
C7C   1    1.184764    0.498363    0.597779    11.00000    0.02355    0.03271 =
         0.02561    0.00120   -0.00769   -0.00460
AFIX  43
H7C   2    1.170731    0.535369    0.550454    11.00000   -1.20000
AFIX   0
C8C   1    1.285528    0.469869    0.606152    11.00000    0.02141    0.03450 =
         0.03300   -0.00324   -0.00210   -0.00773
AFIX  43
H8C   2    1.339411    0.487984    0.563251    11.00000   -1.20000
AFIX   0
C9C   1    1.233666    0.395306    0.729974    11.00000    0.02818    0.02932 =
         0.03140   -0.00125   -0.00805   -0.00493
AFIX  43
H9C   2    1.249811    0.359884    0.777146    11.00000   -1.20000
AFIX   0
C10C  1    1.129996    0.419926    0.726725    11.00000    0.02724    0.02672 =
         0.02696   -0.00101   -0.00457   -0.00455
AFIX  43
H10C  2    1.077560    0.400879    0.770424    11.00000   -1.20000
AFIX   0
C11C  1    0.678746    0.575764    0.631998    11.00000    0.01638    0.02698 =
         0.03584   -0.00566   -0.00750   -0.00846
AFIX  23
H11G  2    0.635119    0.541012    0.677177    11.00000   -1.20000
H11H  2    0.676378    0.554669    0.584103    11.00000   -1.20000
AFIX   0
C12C  1    0.635571    0.681372    0.627603    11.00000    0.01455    0.02309 =
         0.02463    0.00118   -0.00574   -0.00735
C13C  1    0.605185    0.724876    0.693820    11.00000    0.01965    0.02283 =
         0.02418    0.00321   -0.00916   -0.00466
C14C  1    0.563973    0.820537    0.692060    11.00000    0.02014    0.02954 =
         0.02736   -0.00649   -0.00965   -0.00501
C15C  1    0.552337    0.876267    0.622361    11.00000    0.01814    0.01795 =
         0.04219   -0.00031   -0.01174   -0.00490
C16C  1    0.579353    0.835422    0.555798    11.00000    0.02328    0.02618 =
         0.03031    0.00786   -0.01232   -0.00773
C17C  1    0.620779    0.739248    0.559174    11.00000    0.01820    0.03028 =
         0.02163   -0.00223   -0.00523   -0.00632
 
HKLF   4
 
REM  mm-bipy-1 in P -1
REM R1 =  0.0433 for   8823 Fo > 4sig(Fo)  and  0.0734 for all  12016 data
REM    961 parameters refined using     12 restraints
 
END
 
WGHT      0.0000      5.1533
REM Highest difference peak  0.503,  deepest hole -0.484,  1-sigma level  0.087
Q1    1   0.8399  0.3833  0.9368  11.00000  0.05    0.50
Q2    1   0.9202  0.8909  0.9102  11.00000  0.05    0.47
Q3    1   0.5421  0.9522  0.9352  11.00000  0.05    0.40
Q4    1   0.5792  0.2200  1.0943  11.00000  0.05    0.36
Q5    1   0.5973  0.2262  0.7781  11.00000  0.05    0.36
Q6    1   0.9064  0.8159  0.5698  11.00000  0.05    0.35
Q7    1   0.7398  0.1745  0.9020  11.00000  0.05    0.35
Q8    1   0.5012  0.4021  1.0449  11.00000  0.05    0.35
Q9    1   1.1177  0.1437  0.9291  11.00000  0.05    0.35
Q10   1   1.3641  0.3613  0.7428  11.00000  0.05    0.35
Q11   1   1.0598  0.6385  0.8406  11.00000  0.05    0.34
Q12   1   0.7581  0.7965  0.4681  11.00000  0.05    0.33
Q13   1   0.7368  0.8398  0.9327  11.00000  0.05    0.33
Q14   1   0.8840  0.9197  0.9685  11.00000  0.05    0.33
Q15   1   0.5964  0.8378  0.6577  11.00000  0.05    0.33
Q16   1   0.8371  0.3338  0.5407  11.00000  0.05    0.32
Q17   1   0.5594  0.7836  0.5807  11.00000  0.05    0.32
Q18   1   0.7618  0.9082  0.9471  11.00000  0.05    0.32
Q19   1   0.6333  0.7033  0.6663  11.00000  0.05    0.32
Q20   1   0.6481  0.1993  0.4358  11.00000  0.05    0.32
Q21   1   0.6577  0.8962  0.5787  11.00000  0.05    0.32
Q22   1   0.7436  0.0388  0.9577  11.00000  0.05    0.32
Q23   1   0.6229  0.7944  0.9068  11.00000  0.05    0.32
Q24   1   0.8233  0.2623  1.0079  11.00000  0.05    0.32
Q25   1   0.8625  0.6314  0.4019  11.00000  0.05    0.32
;

# start Validation Reply Form
_vrf_PLAT112_mm-bipy-1           
;
PROBLEM: ADDSYM Detects Additional (Pseudo) Symm. Elem... Y Check 
RESPONSE: Checked platon addsymm and newsym no spacegroup or symmetry change
suggested.
;
_vrf_PLAT910_mm-bipy-1           
;
PROBLEM: Missing # of FCF Reflections Below Th(Min) ..... 11 Why ? 
RESPONSE: The crystal was weaker scatterer than estimated and the beamstop
was set to slightly too close distance from crystal. This does not have 
significant effect on the result.
;
# end Validation Reply Form
_database_code_depnum_ccdc_archive 'CCDC 1005274'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-191

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H8 F5 N2, Br'
_chemical_formula_sum            'C11 H8 Br F5 N2'
_chemical_formula_weight         343.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.1966(2)
_cell_length_b                   11.8976(2)
_cell_length_c                   10.2358(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.2530(10)
_cell_angle_gamma                90.00
_cell_volume                     1217.88(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3075
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    3.425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4264
_exptl_absorpt_correction_T_max  0.5063
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7035
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.42
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2137
_reflns_number_gt                1892
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, et al., 2006)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0212P)²+0.5993P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2137
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_ref         0.0530
_refine_ls_wR_factor_gt          0.0517
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.55376(2) 0.101277(17) 0.31400(2) 0.02162(9) Uani 1 1 d . . .
F6 F 0.97575(13) 0.20063(12) 0.25394(14) 0.0335(3) Uani 1 1 d . . .
F7 F 0.93687(13) 0.17974(12) 0.50607(13) 0.0352(3) Uani 1 1 d . . .
F8 F 0.74064(14) 0.30163(13) 0.58760(12) 0.0374(4) Uani 1 1 d . . .
F9 F 0.58787(13) 0.44442(13) 0.41720(15) 0.0380(4) Uani 1 1 d . . .
F10 F 0.62350(13) 0.46353(11) 0.16510(14) 0.0341(3) Uani 1 1 d . . .
N1 N 0.77632(18) 0.23550(15) -0.01365(17) 0.0204(4) Uani 1 1 d . . .
N2 N 0.75408(17) 0.11122(15) -0.16967(17) 0.0196(4) Uani 1 1 d . . .
C1 C 0.8198(2) 0.20359(19) -0.1227(2) 0.0216(5) Uani 1 1 d . . .
H1 H 0.8863 0.2406 -0.1602 0.026 Uiso 1 1 calc R . .
C2 C 0.6652(2) 0.08366(18) -0.0887(2) 0.0203(5) Uani 1 1 d . . .
H2 H 0.6053 0.0217 -0.0999 0.024 Uiso 1 1 calc R . .
C3 C 0.6796(2) 0.16127(18) 0.0093(2) 0.0196(5) Uani 1 1 d . . .
H3 H 0.6322 0.1641 0.0804 0.024 Uiso 1 1 calc R . .
C4 C 0.8193(3) 0.34065(19) 0.0605(2) 0.0290(5) Uani 1 1 d . . .
H4A H 0.7664 0.4046 0.0162 0.035 Uiso 1 1 calc R . .
H4B H 0.9147 0.3551 0.0594 0.035 Uiso 1 1 calc R . .
C5 C 0.8005(2) 0.33196(18) 0.2020(2) 0.0217(5) Uani 1 1 d . . .
C6 C 0.8791(2) 0.26168(18) 0.2932(2) 0.0232(5) Uani 1 1 d . . .
C7 C 0.8612(2) 0.25120(19) 0.4225(2) 0.0250(5) Uani 1 1 d . . .
C8 C 0.7629(2) 0.3136(2) 0.4629(2) 0.0256(5) Uani 1 1 d . . .
C9 C 0.6850(2) 0.38538(19) 0.3763(2) 0.0254(5) Uani 1 1 d . . .
C10 C 0.7037(2) 0.39358(18) 0.2474(2) 0.0229(5) Uani 1 1 d . . .
C11 C 0.7744(2) 0.0465(2) -0.2862(2) 0.0293(5) Uani 1 1 d . . .
H11A H 0.8507 0.0775 -0.3196 0.044 Uiso 1 1 calc R . .
H11B H 0.6939 0.0512 -0.3562 0.044 Uiso 1 1 calc R . .
H11C H 0.7922 -0.0322 -0.2608 0.044 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02176(13) 0.01811(13) 0.02651(14) -0.00172(9) 0.00849(9) -0.00016(9)
F6 0.0354(7) 0.0268(8) 0.0414(8) -0.0021(6) 0.0157(6) 0.0041(6)
F7 0.0362(8) 0.0345(8) 0.0313(8) 0.0115(6) -0.0019(6) -0.0025(6)
F8 0.0470(8) 0.0489(9) 0.0189(7) -0.0041(6) 0.0126(6) -0.0131(7)
F9 0.0295(7) 0.0427(9) 0.0440(9) -0.0137(7) 0.0128(7) 0.0008(7)
F10 0.0343(8) 0.0286(8) 0.0351(8) 0.0021(6) -0.0040(6) 0.0006(6)
N1 0.0252(9) 0.0175(10) 0.0186(9) -0.0002(7) 0.0044(8) -0.0034(8)
N2 0.0225(9) 0.0198(10) 0.0180(9) -0.0013(7) 0.0072(7) -0.0016(8)
C1 0.0243(11) 0.0222(12) 0.0193(11) 0.0013(9) 0.0065(9) -0.0039(9)
C2 0.0197(11) 0.0212(11) 0.0207(11) 0.0015(9) 0.0055(9) -0.0029(9)
C3 0.0206(11) 0.0210(12) 0.0181(11) 0.0016(9) 0.0058(9) -0.0015(9)
C4 0.0462(15) 0.0206(12) 0.0219(12) -0.0033(10) 0.0105(11) -0.0111(11)
C5 0.0278(12) 0.0179(12) 0.0196(11) -0.0036(9) 0.0051(9) -0.0093(9)
C6 0.0232(11) 0.0191(11) 0.0285(12) -0.0049(9) 0.0081(10) -0.0051(9)
C7 0.0262(12) 0.0246(12) 0.0220(12) 0.0038(9) -0.0010(10) -0.0079(10)
C8 0.0297(12) 0.0300(13) 0.0175(11) -0.0040(10) 0.0059(9) -0.0120(10)
C9 0.0213(11) 0.0252(12) 0.0307(13) -0.0101(10) 0.0072(10) -0.0066(10)
C10 0.0237(11) 0.0179(11) 0.0246(12) -0.0003(9) -0.0017(9) -0.0058(10)
C11 0.0410(14) 0.0267(13) 0.0245(12) -0.0084(10) 0.0167(11) -0.0070(11)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F6 C6 1.347(3) . ?
F7 C7 1.338(3) . ?
F8 C8 1.346(2) . ?
F9 C9 1.346(3) . ?
F10 C10 1.343(3) . ?
N1 C1 1.334(3) . ?
N1 C3 1.378(3) . ?
N1 C4 1.484(3) . ?
N2 C1 1.328(3) . ?
N2 C2 1.381(3) . ?
N2 C11 1.468(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.350(3) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.501(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.380(3) . ?
C5 C6 1.386(3) . ?
C6 C7 1.377(3) . ?
C7 C8 1.375(3) . ?
C8 C9 1.368(3) . ?
C9 C10 1.373(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C3 109.03(18) . . ?
C1 N1 C4 123.67(18) . . ?
C3 N1 C4 127.08(18) . . ?
C1 N2 C2 108.84(17) . . ?
C1 N2 C11 125.95(18) . . ?
C2 N2 C11 125.19(18) . . ?
N2 C1 N1 108.19(18) . . ?
N2 C1 H1 125.9 . . ?
N1 C1 H1 125.9 . . ?
C3 C2 N2 107.12(19) . . ?
C3 C2 H2 126.4 . . ?
N2 C2 H2 126.4 . . ?
C2 C3 N1 106.82(18) . . ?
C2 C3 H3 126.6 . . ?
N1 C3 H3 126.6 . . ?
N1 C4 C5 110.76(17) . . ?
N1 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C10 C5 C6 116.8(2) . . ?
C10 C5 C4 121.5(2) . . ?
C6 C5 C4 121.7(2) . . ?
F6 C6 C7 118.6(2) . . ?
F6 C6 C5 119.0(2) . . ?
C7 C6 C5 122.3(2) . . ?
F7 C7 C8 120.9(2) . . ?
F7 C7 C6 120.3(2) . . ?
C8 C7 C6 118.8(2) . . ?
F8 C8 C9 119.8(2) . . ?
F8 C8 C7 119.7(2) . . ?
C9 C8 C7 120.5(2) . . ?
F9 C9 C8 119.6(2) . . ?
F9 C9 C10 120.7(2) . . ?
C8 C9 C10 119.7(2) . . ?
F10 C10 C9 117.7(2) . . ?
F10 C10 C5 120.4(2) . . ?
C9 C10 C5 121.9(2) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N2 C1 N1 0.4(2) . . . . ?
C11 N2 C1 N1 -178.0(2) . . . . ?
C3 N1 C1 N2 -0.1(2) . . . . ?
C4 N1 C1 N2 -175.06(19) . . . . ?
C1 N2 C2 C3 -0.5(2) . . . . ?
C11 N2 C2 C3 177.9(2) . . . . ?
N2 C2 C3 N1 0.4(2) . . . . ?
C1 N1 C3 C2 -0.2(2) . . . . ?
C4 N1 C3 C2 174.5(2) . . . . ?
C1 N1 C4 C5 -157.1(2) . . . . ?
C3 N1 C4 C5 28.9(3) . . . . ?
N1 C4 C5 C10 -110.2(2) . . . . ?
N1 C4 C5 C6 69.7(3) . . . . ?
C10 C5 C6 F6 -179.34(19) . . . . ?
C4 C5 C6 F6 0.7(3) . . . . ?
C10 C5 C6 C7 1.2(3) . . . . ?
C4 C5 C6 C7 -178.7(2) . . . . ?
F6 C6 C7 F7 -1.5(3) . . . . ?
C5 C6 C7 F7 177.97(19) . . . . ?
F6 C6 C7 C8 179.83(19) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
F7 C7 C8 F8 -1.0(3) . . . . ?
C6 C7 C8 F8 177.65(19) . . . . ?
F7 C7 C8 C9 -179.17(19) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
F8 C8 C9 F9 0.9(3) . . . . ?
C7 C8 C9 F9 179.0(2) . . . . ?
F8 C8 C9 C10 -177.00(19) . . . . ?
C7 C8 C9 C10 1.1(3) . . . . ?
F9 C9 C10 F10 1.0(3) . . . . ?
C8 C9 C10 F10 178.83(19) . . . . ?
F9 C9 C10 C5 -178.42(19) . . . . ?
C8 C9 C10 C5 -0.6(3) . . . . ?
C6 C5 C10 F10 -179.96(18) . . . . ?
C4 C5 C10 F10 0.0(3) . . . . ?
C6 C5 C10 C9 -0.6(3) . . . . ?
C4 C5 C10 C9 179.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.056

_iucr_refine_instructions_details 
;
TITL mm-191 in P 21/n
CELL   0.71073  10.1966  11.8976  10.2358  90.000 101.253  90.000
ZERR     4       0.0002   0.0002   0.0002   0.000   0.001   0.000
LATT  1
SYMM 1/2-X,1/2+Y,1/2-Z
SFAC        C       H       N       F       BR
UNIT        44      32       8      20       4
L.S.      10
OMIT -3 50.05
OMIT 4 4 2
OMIT -5 4 2
TEMP  -150
SIZE  0.30 0.25 0.23
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.021200    0.599300
FVAR       0.52598
BR1   5    0.553764    0.101277    0.313997    11.00000    0.02176    0.01811 =
         0.02651   -0.00172    0.00849   -0.00016
F6    4    0.975751    0.200635    0.253943    11.00000    0.03543    0.02683 =
         0.04141   -0.00206    0.01565    0.00405
F7    4    0.936873    0.179742    0.506073    11.00000    0.03620    0.03453 =
         0.03135    0.01146   -0.00191   -0.00249
F8    4    0.740645    0.301626    0.587600    11.00000    0.04698    0.04892 =
         0.01888   -0.00408    0.01261   -0.01314
F9    4    0.587865    0.444416    0.417197    11.00000    0.02948    0.04267 =
         0.04404   -0.01366    0.01284    0.00082
F10   4    0.623495    0.463527    0.165104    11.00000    0.03429    0.02859 =
         0.03514    0.00211   -0.00402    0.00062
N1    3    0.776319    0.235501   -0.013647    11.00000    0.02520    0.01749 =
         0.01862   -0.00020    0.00436   -0.00339
N2    3    0.754079    0.111223   -0.169666    11.00000    0.02254    0.01978 =
         0.01795   -0.00126    0.00723   -0.00156
C1    1    0.819800    0.203593   -0.122663    11.00000    0.02426    0.02222 =
         0.01933    0.00134    0.00647   -0.00392
AFIX  43
H1    2    0.886299    0.240571   -0.160189    11.00000   -1.20000
AFIX   0
C2    1    0.665232    0.083658   -0.088695    11.00000    0.01973    0.02122 =
         0.02070    0.00151    0.00549   -0.00286
AFIX  43
H2    2    0.605263    0.021734   -0.099869    11.00000   -1.20000
AFIX   0
C3    1    0.679641    0.161267    0.009316    11.00000    0.02062    0.02103 =
         0.01812    0.00162    0.00582   -0.00155
AFIX  43
H3    2    0.632216    0.164126    0.080446    11.00000   -1.20000
AFIX   0
C4    1    0.819297    0.340652    0.060471    11.00000    0.04622    0.02056 =
         0.02189   -0.00330    0.01054   -0.01113
AFIX  23
H4A   2    0.766377    0.404608    0.016196    11.00000   -1.20000
H4B   2    0.914691    0.355129    0.059392    11.00000   -1.20000
AFIX   0
C5    1    0.800463    0.331956    0.201970    11.00000    0.02776    0.01786 =
         0.01955   -0.00364    0.00515   -0.00934
C6    1    0.879081    0.261685    0.293158    11.00000    0.02320    0.01915 =
         0.02853   -0.00492    0.00813   -0.00510
C7    1    0.861229    0.251201    0.422539    11.00000    0.02621    0.02461 =
         0.02198    0.00376   -0.00100   -0.00795
C8    1    0.762899    0.313601    0.462946    11.00000    0.02971    0.02999 =
         0.01752   -0.00398    0.00587   -0.01201
C9    1    0.684957    0.385376    0.376292    11.00000    0.02129    0.02520 =
         0.03070   -0.01010    0.00723   -0.00657
C10   1    0.703747    0.393584    0.247396    11.00000    0.02366    0.01794 =
         0.02462   -0.00025   -0.00165   -0.00583
C11   1    0.774411    0.046540   -0.286234    11.00000    0.04096    0.02667 =
         0.02450   -0.00844    0.01667   -0.00701
AFIX 137
H11A  2    0.850683    0.077502   -0.319556    11.00000   -1.50000
H11B  2    0.693885    0.051155   -0.356184    11.00000   -1.50000
H11C  2    0.792238   -0.032214   -0.260774    11.00000   -1.50000
HKLF   4
 
REM  mm-191 in P 21/n
REM R1 =  0.0217 for   1892 Fo > 4sig(Fo)  and  0.0261 for all   2137 data
REM    173 parameters refined using      0 restraints
 
END
 
WGHT      0.0212      0.6004
REM Highest difference peak  0.251,  deepest hole -0.254,  1-sigma level  0.056
Q1    1   0.7070  0.1003 -0.1428  11.00000  0.05    0.25
Q2    1   0.7877  0.2634  0.4226  11.00000  0.05    0.25
Q3    1   0.7178  0.4019  0.3238  11.00000  0.05    0.25
Q4    1   0.6749  0.3674  0.3129  11.00000  0.05    0.24
Q5    1   0.7064 -0.0124 -0.3089  11.00000  0.05    0.24
Q6    1   0.7712  0.0812 -0.2236  11.00000  0.05    0.24
Q7    1   0.8601  0.2378  0.3577  11.00000  0.05    0.24
Q8    1   0.8112  0.3295  0.1375  11.00000  0.05    0.24
Q9    1   0.7359  0.3549  0.4220  11.00000  0.05    0.23
Q10   1   0.7984  0.2872  0.0167  11.00000  0.05    0.22
Q11   1   0.8241  0.2079 -0.0494  11.00000  0.05    0.22
Q12   1   0.7744  0.3811  0.2257  11.00000  0.05    0.22
Q13   1   0.8957  0.2207  0.4546  11.00000  0.05    0.21
Q14   1   0.8400  0.3976  0.5590  11.00000  0.05    0.20
Q15   1   0.7642  0.3089  0.5001  11.00000  0.05    0.20
Q16   1   0.8131  0.1183 -0.1235  11.00000  0.05    0.20
Q17   1   0.8183  0.2878  0.2416  11.00000  0.05    0.19
Q18   1   0.7336  0.3388  0.2230  11.00000  0.05    0.19
Q19   1   0.9175  0.2419  0.2758  11.00000  0.05    0.19
Q20   1   0.8726  0.0024 -0.2548  11.00000  0.05    0.19
Q21   1   0.8898  0.2734  0.3790  11.00000  0.05    0.19
Q22   1   0.7337  0.2067 -0.0060  11.00000  0.05    0.19
Q23   1   0.8383  0.3061  0.4583  11.00000  0.05    0.19
Q24   1   0.8593  0.3263  0.2549  11.00000  0.05    0.19
Q25   1   0.6400  0.4430  0.0990  11.00000  0.05    0.19
;
_database_code_depnum_ccdc_archive 'CCDC 1005275'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-307-5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H20 F2 N, Br'
_chemical_formula_sum            'C13 H20 Br F2 N'
_chemical_formula_weight         308.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pna21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   13.4970(2)
_cell_length_b                   13.2580(2)
_cell_length_c                   7.79800(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1395.40(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1996
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    2.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4429
_exptl_absorpt_correction_T_max  0.6043
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17465
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         25.24
_reflns_number_total             2530
_reflns_number_gt                2395
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, et al., 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0138P)²+0.5500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.064(9)
_refine_ls_number_reflns         2530
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_ref         0.0501
_refine_ls_wR_factor_gt          0.0490
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.313088(14) 0.012960(14) 0.25962(6) 0.02246(8) Uani 1 1 d . . .
F10 F -0.15581(11) 0.27778(12) 0.6660(2) 0.0305(4) Uani 1 1 d . . .
F12 F -0.00744(15) -0.02966(12) 0.5232(3) 0.0482(5) Uani 1 1 d . . .
N1 N 0.16087(14) 0.31472(16) 0.2085(2) 0.0154(4) Uani 1 1 d . . .
C1 C 0.25900(16) 0.36312(19) 0.1560(3) 0.0227(6) Uani 1 1 d . . .
H1A H 0.2787 0.4121 0.2455 0.027 Uiso 1 1 calc R . .
H1B H 0.2486 0.4012 0.0483 0.027 Uiso 1 1 calc R . .
C2 C 0.34410(18) 0.2886(2) 0.1291(4) 0.0276(6) Uani 1 1 d . . .
H2A H 0.4040 0.3255 0.0959 0.041 Uiso 1 1 calc R . .
H2B H 0.3264 0.2408 0.0382 0.041 Uiso 1 1 calc R . .
H2C H 0.3564 0.2517 0.2359 0.041 Uiso 1 1 calc R . .
C3 C 0.13657(18) 0.22369(19) 0.0987(3) 0.0201(5) Uani 1 1 d . . .
H3A H 0.0721 0.1960 0.1367 0.024 Uiso 1 1 calc R . .
H3B H 0.1874 0.1713 0.1195 0.024 Uiso 1 1 calc R . .
C4 C 0.1311(2) 0.2434(2) -0.0927(3) 0.0285(6) Uani 1 1 d . . .
H4A H 0.1148 0.1806 -0.1526 0.043 Uiso 1 1 calc R . .
H4B H 0.1952 0.2686 -0.1333 0.043 Uiso 1 1 calc R . .
H4C H 0.0797 0.2938 -0.1159 0.043 Uiso 1 1 calc R . .
C5 C 0.07944(16) 0.39394(18) 0.1866(3) 0.0200(5) Uani 1 1 d . . .
H5A H 0.0731 0.4100 0.0631 0.024 Uiso 1 1 calc R . .
H5B H 0.0158 0.3643 0.2246 0.024 Uiso 1 1 calc R . .
C6 C 0.0963(2) 0.49130(17) 0.2841(5) 0.0282(8) Uani 1 1 d . . .
H6A H 0.0408 0.5374 0.2635 0.042 Uiso 1 1 calc R . .
H6B H 0.1580 0.5227 0.2449 0.042 Uiso 1 1 calc R . .
H6C H 0.1011 0.4768 0.4071 0.042 Uiso 1 1 calc R . .
C7 C 0.16949(17) 0.2798(2) 0.3934(3) 0.0179(5) Uani 1 1 d . . .
H7A H 0.2274 0.2344 0.4031 0.022 Uiso 1 1 calc R . .
H7B H 0.1824 0.3393 0.4667 0.022 Uiso 1 1 calc R . .
C8 C 0.07913(19) 0.22522(19) 0.4620(3) 0.0182(5) Uani 1 1 d . . .
C9 C 0.0001(2) 0.27938(19) 0.5317(3) 0.0200(5) Uani 1 1 d . . .
H9 H 0.0005 0.3510 0.5340 0.024 Uiso 1 1 calc R . .
C10 C -0.07867(18) 0.2254(2) 0.5970(3) 0.0219(5) Uani 1 1 d . . .
C11 C -0.08489(18) 0.12232(19) 0.5976(3) 0.0241(6) Uani 1 1 d . . .
H11 H -0.1404 0.0874 0.6434 0.029 Uiso 1 1 calc R . .
C12 C -0.0048(2) 0.0728(2) 0.5272(4) 0.0281(6) Uani 1 1 d . . .
C13 C 0.07727(19) 0.12074(19) 0.4615(3) 0.0242(6) Uani 1 1 d . . .
H13 H 0.1313 0.0831 0.4169 0.029 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.01985(11) 0.02262(12) 0.02491(12) 0.0045(2) 0.00039(17) 0.00026(8)
F10 0.0279(8) 0.0296(9) 0.0342(9) -0.0039(7) 0.0107(7) 0.0023(7)
F12 0.0449(11) 0.0176(10) 0.0820(15) 0.0118(12) 0.0247(10) -0.0026(10)
N1 0.0136(9) 0.0176(10) 0.0150(11) 0.0045(8) -0.0021(7) -0.0026(8)
C1 0.0161(12) 0.0232(14) 0.0288(14) 0.0081(11) -0.0010(11) -0.0052(10)
C2 0.0149(12) 0.0354(16) 0.0324(15) 0.0100(13) 0.0019(11) -0.0028(11)
C3 0.0216(13) 0.0189(14) 0.0197(13) 0.0008(10) -0.0011(11) -0.0055(11)
C4 0.0349(16) 0.0317(15) 0.0190(13) -0.0012(11) -0.0027(12) -0.0058(12)
C5 0.0159(11) 0.0233(14) 0.0207(12) 0.0068(10) -0.0009(10) 0.0021(9)
C6 0.0283(12) 0.0206(12) 0.036(2) 0.0037(13) -0.0032(15) 0.0007(9)
C7 0.0180(12) 0.0210(14) 0.0149(12) 0.0032(11) -0.0034(11) -0.0009(10)
C8 0.0187(13) 0.0227(13) 0.0134(11) 0.0035(10) -0.0040(10) -0.0039(10)
C9 0.0256(12) 0.0186(13) 0.0157(12) 0.0003(9) -0.0010(10) -0.0008(10)
C10 0.0216(13) 0.0286(14) 0.0155(12) -0.0017(10) 0.0020(11) 0.0022(10)
C11 0.0197(12) 0.0266(15) 0.0259(14) 0.0049(11) 0.0028(11) -0.0035(10)
C12 0.0330(15) 0.0159(14) 0.0356(16) 0.0071(12) 0.0024(13) -0.0029(13)
C13 0.0245(14) 0.0217(13) 0.0262(13) 0.0080(11) 0.0032(11) 0.0025(11)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F10 C10 1.362(3) . ?
F12 C12 1.359(3) . ?
N1 C3 1.516(3) . ?
N1 C7 1.519(3) . ?
N1 C1 1.528(3) . ?
N1 C5 1.530(3) . ?
C1 C2 1.530(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.517(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.515(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.516(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.385(4) . ?
C8 C9 1.396(4) . ?
C9 C10 1.378(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.370(4) . ?
C11 C12 1.379(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(4) . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C7 108.05(19) . . ?
C3 N1 C1 111.76(18) . . ?
C7 N1 C1 108.42(17) . . ?
C3 N1 C5 109.17(17) . . ?
C7 N1 C5 111.74(18) . . ?
C1 N1 C5 107.74(18) . . ?
N1 C1 C2 114.6(2) . . ?
N1 C1 H1A 108.6 . . ?
C2 C1 H1A 108.6 . . ?
N1 C1 H1B 108.6 . . ?
C2 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 115.4(2) . . ?
N1 C3 H3A 108.4 . . ?
C4 C3 H3A 108.4 . . ?
N1 C3 H3B 108.4 . . ?
C4 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N1 114.89(19) . . ?
C6 C5 H5A 108.5 . . ?
N1 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
N1 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N1 114.77(19) . . ?
C8 C7 H7A 108.6 . . ?
N1 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
N1 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C13 C8 C9 120.1(2) . . ?
C13 C8 C7 119.4(2) . . ?
C9 C8 C7 120.5(2) . . ?
C10 C9 C8 117.8(2) . . ?
C10 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
F10 C10 C11 117.4(2) . . ?
F10 C10 C9 118.1(2) . . ?
C11 C10 C9 124.5(2) . . ?
C10 C11 C12 115.2(2) . . ?
C10 C11 H11 122.4 . . ?
C12 C11 H11 122.4 . . ?
F12 C12 C13 118.3(3) . . ?
F12 C12 C11 117.7(2) . . ?
C13 C12 C11 124.0(3) . . ?
C12 C13 C8 118.4(2) . . ?
C12 C13 H13 120.8 . . ?
C8 C13 H13 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 C2 -46.3(3) . . . . ?
C7 N1 C1 C2 72.7(3) . . . . ?
C5 N1 C1 C2 -166.2(2) . . . . ?
C7 N1 C3 C4 -176.5(2) . . . . ?
C1 N1 C3 C4 -57.3(3) . . . . ?
C5 N1 C3 C4 61.8(3) . . . . ?
C3 N1 C5 C6 -177.6(2) . . . . ?
C7 N1 C5 C6 62.9(3) . . . . ?
C1 N1 C5 C6 -56.1(3) . . . . ?
C3 N1 C7 C8 -55.8(2) . . . . ?
C1 N1 C7 C8 -177.1(2) . . . . ?
C5 N1 C7 C8 64.3(3) . . . . ?
N1 C7 C8 C13 96.9(3) . . . . ?
N1 C7 C8 C9 -85.7(3) . . . . ?
C13 C8 C9 C10 -0.7(3) . . . . ?
C7 C8 C9 C10 -178.0(2) . . . . ?
C8 C9 C10 F10 179.6(2) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
F10 C10 C11 C12 -179.7(2) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C11 C12 F12 -179.4(2) . . . . ?
C10 C11 C12 C13 0.7(5) . . . . ?
F12 C12 C13 C8 178.6(2) . . . . ?
C11 C12 C13 C8 -1.6(5) . . . . ?
C9 C8 C13 C12 1.5(4) . . . . ?
C7 C8 C13 C12 178.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.051

_iucr_refine_instructions_details 
;
TITL mm-307-5 in P 21 c n
REM  transformed to space group : Pna21
CELL   0.71073 13.4970 13.2580  7.7980   90.000   90.000   90.000
ZERR   4        0.0002  0.0002  0.0001    0.000    0.000    0.000
LATT   -1
SYMM   -X,-Y,1/2+Z
SYMM   1/2-X,1/2+Y,1/2+Z
SYMM   1/2+X,1/2-Y,+Z
SFAC        C       H       N       F       BR
UNIT        52      80       4       8       4
L.S.      10
OMIT -3 50.5
OMIT 0 2 0
TEMP  -150
SIZE  0.33 0.21 0.19
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.013800    0.550000
FVAR       0.55699
BR1   5    0.313088    0.012960    0.259617    11.00000    0.01985    0.02262 =
         0.02491    0.00452    0.00039    0.00026
F10   4   -0.155810    0.277783    0.666018    11.00000    0.02787    0.02959 =
         0.03419   -0.00388    0.01066    0.00227
F12   4   -0.007439   -0.029662    0.523170    11.00000    0.04490    0.01762 =
         0.08201    0.01181    0.02465   -0.00258
N1    3    0.160866    0.314724    0.208483    11.00000    0.01360    0.01760 =
         0.01502    0.00448   -0.00207   -0.00263
C1    1    0.258997    0.363120    0.155988    11.00000    0.01607    0.02323 =
         0.02875    0.00812   -0.00101   -0.00517
AFIX  23
H1A   2    0.278674    0.412110    0.245544    11.00000   -1.20000
H1B   2    0.248638    0.401199    0.048263    11.00000   -1.20000
AFIX   0
C2    1    0.344099    0.288586    0.129088    11.00000    0.01488    0.03541 =
         0.03241    0.00995    0.00187   -0.00277
AFIX  33
H2A   2    0.404024    0.325494    0.095949    11.00000   -1.50000
H2B   2    0.326380    0.240825    0.038206    11.00000   -1.50000
H2C   2    0.356415    0.251686    0.235876    11.00000   -1.50000
AFIX   0
C3    1    0.136568    0.223693    0.098694    11.00000    0.02161    0.01891 =
         0.01965    0.00084   -0.00112   -0.00548
AFIX  23
H3A   2    0.072086    0.196017    0.136741    11.00000   -1.20000
H3B   2    0.187421    0.171294    0.119529    11.00000   -1.20000
AFIX   0
C4    1    0.131113    0.243418   -0.092721    11.00000    0.03486    0.03167 =
         0.01899   -0.00124   -0.00268   -0.00579
AFIX  33
H4A   2    0.114831    0.180588   -0.152626    11.00000   -1.50000
H4B   2    0.195244    0.268562   -0.133286    11.00000   -1.50000
H4C   2    0.079741    0.293846   -0.115893    11.00000   -1.50000
AFIX   0
C5    1    0.079442    0.393943    0.186608    11.00000    0.01594    0.02334 =
         0.02070    0.00684   -0.00094    0.00214
AFIX  23
H5A   2    0.073108    0.409990    0.063105    11.00000   -1.20000
H5B   2    0.015777    0.364345    0.224594    11.00000   -1.20000
AFIX   0
C6    1    0.096330    0.491301    0.284115    11.00000    0.02834    0.02055 =
         0.03579    0.00375   -0.00322    0.00066
AFIX  33
H6A   2    0.040808    0.537361    0.263471    11.00000   -1.50000
H6B   2    0.158012    0.522734    0.244874    11.00000   -1.50000
H6C   2    0.101093    0.476773    0.407061    11.00000   -1.50000
AFIX   0
C7    1    0.169492    0.279779    0.393391    11.00000    0.01802    0.02095 =
         0.01487    0.00322   -0.00342   -0.00086
AFIX  23
H7A   2    0.227441    0.234358    0.403082    11.00000   -1.20000
H7B   2    0.182422    0.339305    0.466703    11.00000   -1.20000
AFIX   0
C8    1    0.079128    0.225220    0.461983    11.00000    0.01869    0.02266 =
         0.01337    0.00347   -0.00401   -0.00386
C9    1    0.000072    0.279376    0.531687    11.00000    0.02557    0.01863 =
         0.01574    0.00027   -0.00098   -0.00083
AFIX  43
H9    2    0.000535    0.351016    0.534049    11.00000   -1.20000
AFIX   0
C10   1   -0.078671    0.225431    0.596962    11.00000    0.02159    0.02857 =
         0.01553   -0.00170    0.00198    0.00224
C11   1   -0.084890    0.122325    0.597643    11.00000    0.01972    0.02660 =
         0.02589    0.00485    0.00277   -0.00353
AFIX  43
H11   2   -0.140407    0.087439    0.643362    11.00000   -1.20000
AFIX   0
C12   1   -0.004833    0.072785    0.527245    11.00000    0.03295    0.01594 =
         0.03555    0.00710    0.00244   -0.00291
C13   1    0.077266    0.120742    0.461505    11.00000    0.02455    0.02173 =
         0.02623    0.00802    0.00316    0.00251
AFIX  43
H13   2    0.131335    0.083110    0.416893    11.00000   -1.20000
HKLF   4
 
REM  mm-307-5 in P 21 c n
REM R1 =  0.0217 for   2395 Fo > 4sig(Fo)  and  0.0242 for all   2530 data
REM    154 parameters refined using      1 restraints
 
END
 
WGHT      0.0138      0.5494
REM Highest difference peak  0.175,  deepest hole -0.439,  1-sigma level  0.051
Q1    1   0.0876  0.6099  0.4193  11.00000  0.05    0.18
Q2    1  -0.1926  0.0745  0.7520  11.00000  0.05    0.17
Q3    1   0.1258  0.0903  0.2561  11.00000  0.05    0.16
Q4    1   0.1284  0.5422  0.1802  11.00000  0.05    0.16
Q5    1   0.3388  0.1768  0.1480  11.00000  0.05    0.15
Q6    1   0.3866  0.0816  0.1370  11.00000  0.05    0.15
Q7    1   0.1417  0.0357  0.3787  11.00000  0.05    0.15
Q8    1  -0.0829 -0.0606  0.3882  11.00000  0.05    0.15
Q9    1   0.1562  0.1932 -0.1286  11.00000  0.05    0.15
Q10   1   0.0537  0.1588  0.2590  11.00000  0.05    0.14
Q11   1   0.0990  0.2638  0.6616  11.00000  0.05    0.14
Q12   1   0.2165  0.6043  0.0835  11.00000  0.05    0.14
Q13   1   0.3463  0.2741  0.0212  11.00000  0.05    0.14
Q14   1   0.3958  0.2668 -0.1134  11.00000  0.05    0.14
Q15   1  -0.1351 -0.0352  0.6516  11.00000  0.05    0.14
Q16   1   0.1604  0.5996  0.0862  11.00000  0.05    0.13
Q17   1   0.1215  0.4682  0.4212  11.00000  0.05    0.13
Q18   1   0.1944  0.3987  0.5314  11.00000  0.05    0.13
Q19   1   0.2611  0.3788  0.0765  11.00000  0.05    0.13
Q20   1  -0.0468  0.1353  0.8259  11.00000  0.05    0.13
Q21   1   0.2019  0.1367  0.2713  11.00000  0.05    0.13
Q22   1   0.3358  0.2203  0.2757  11.00000  0.05    0.13
Q23   1   0.1549  0.5965  0.4266  11.00000  0.05    0.13
Q24   1   0.0365  0.1128  0.4527  11.00000  0.05    0.13
Q25   1   0.0351  0.4413  0.6197  11.00000  0.05    0.13
;
_database_code_depnum_ccdc_archive 'CCDC 1005276'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-303-5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H19 F3 N, H2 O, Br'
_chemical_formula_sum            'C13 H21 Br F3 N O'
_chemical_formula_weight         344.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.9329(3)
_cell_length_b                   8.3923(2)
_cell_length_c                   12.8666(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.0190(10)
_cell_angle_gamma                90.00
_cell_volume                     1500.78(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3877
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    2.764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4911
_exptl_absorpt_correction_T_max  0.7696
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8720
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2712
_reflns_number_gt                2354
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, et al., 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0197P)²+0.5313P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2712
_refine_ls_number_parameters     178
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0227
_refine_ls_wR_factor_ref         0.0542
_refine_ls_wR_factor_gt          0.0524
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.676555(14) 0.52904(2) 0.600229(15) 0.02313(8) Uani 1 1 d . . .
F10 F 1.00324(9) 0.33230(17) 0.55336(10) 0.0387(3) Uani 1 1 d . . .
F11 F 1.07556(8) 0.09614(16) 0.44005(10) 0.0345(3) Uani 1 1 d . . .
F12 F 0.97490(10) -0.01507(15) 0.26872(10) 0.0370(3) Uani 1 1 d . . .
N1 N 0.70529(11) 0.48620(18) 0.23446(12) 0.0161(3) Uani 1 1 d . . .
C1 C 0.60408(13) 0.5552(2) 0.23126(15) 0.0205(4) Uani 1 1 d . . .
H1A H 0.5932 0.5989 0.3009 0.025 Uiso 1 1 calc R . .
H1B H 0.6001 0.6451 0.1813 0.025 Uiso 1 1 calc R . .
C2 C 0.52403(14) 0.4388(3) 0.20077(17) 0.0280(5) Uani 1 1 d . . .
H2A H 0.4619 0.4936 0.2005 0.042 Uiso 1 1 calc R . .
H2B H 0.5255 0.3510 0.2510 0.042 Uiso 1 1 calc R . .
H2C H 0.5328 0.3966 0.1311 0.042 Uiso 1 1 calc R . .
C3 C 0.77837(14) 0.6187(2) 0.25525(14) 0.0187(4) Uani 1 1 d . . .
H3A H 0.8429 0.5699 0.2669 0.022 Uiso 1 1 calc R . .
H3B H 0.7789 0.6857 0.1920 0.022 Uiso 1 1 calc R . .
C4 C 0.76164(15) 0.7256(3) 0.34697(15) 0.0249(5) Uani 1 1 d . . .
H4A H 0.8121 0.8071 0.3536 0.037 Uiso 1 1 calc R . .
H4B H 0.7633 0.6617 0.4108 0.037 Uiso 1 1 calc R . .
H4C H 0.6987 0.7773 0.3358 0.037 Uiso 1 1 calc R . .
C5 C 0.72489(14) 0.4079(2) 0.13148(14) 0.0192(4) Uani 1 1 d . . .
H5A H 0.7943 0.3822 0.1325 0.023 Uiso 1 1 calc R . .
H5B H 0.6890 0.3062 0.1257 0.023 Uiso 1 1 calc R . .
C6 C 0.69776(15) 0.5075(2) 0.03519(15) 0.0225(4) Uani 1 1 d . . .
H6A H 0.7131 0.4484 -0.0272 0.034 Uiso 1 1 calc R . .
H6B H 0.7341 0.6076 0.0389 0.034 Uiso 1 1 calc R . .
H6C H 0.6287 0.5308 0.0318 0.034 Uiso 1 1 calc R . .
C7 C 0.71328(14) 0.3607(2) 0.32103(15) 0.0191(4) Uani 1 1 d . . .
H7A H 0.6898 0.4084 0.3849 0.023 Uiso 1 1 calc R . .
H7B H 0.6698 0.2712 0.3003 0.023 Uiso 1 1 calc R . .
C8 C 0.81255(13) 0.2941(2) 0.34735(14) 0.0181(4) Uani 1 1 d . . .
C9 C 0.86471(14) 0.3498(2) 0.43672(15) 0.0218(4) Uani 1 1 d . . .
H9 H 0.8398 0.4331 0.4770 0.026 Uiso 1 1 calc R . .
C10 C 0.95263(14) 0.2824(3) 0.46566(15) 0.0247(5) Uani 1 1 d . . .
C11 C 0.99040(14) 0.1629(3) 0.40931(16) 0.0252(5) Uani 1 1 d . . .
C12 C 0.93809(15) 0.1075(2) 0.32195(16) 0.0244(5) Uani 1 1 d . . .
C13 C 0.84939(14) 0.1700(2) 0.29027(15) 0.0213(4) Uani 1 1 d . . .
H13 H 0.8139 0.1290 0.2304 0.026 Uiso 1 1 calc R . .
O1 O 0.47322(12) 0.7256(2) 0.53448(13) 0.0374(4) Uani 1 1 d D . .
H1O1 H 0.4412(19) 0.661(3) 0.4921(19) 0.056 Uiso 1 1 d D . .
H1O2 H 0.5256(15) 0.673(3) 0.550(2) 0.056 Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02642(12) 0.01928(12) 0.02339(12) -0.00107(8) -0.00038(8) 0.00212(8)
F10 0.0353(7) 0.0448(9) 0.0334(7) -0.0036(6) -0.0163(6) 0.0045(6)
F11 0.0211(6) 0.0420(8) 0.0403(7) 0.0111(6) 0.0003(6) 0.0107(6)
F12 0.0398(8) 0.0314(8) 0.0400(7) -0.0047(6) 0.0047(6) 0.0155(6)
N1 0.0164(8) 0.0152(9) 0.0166(8) 0.0019(6) 0.0002(6) 0.0008(6)
C1 0.0161(10) 0.0245(12) 0.0208(10) 0.0012(8) 0.0011(8) 0.0057(8)
C2 0.0192(11) 0.0341(14) 0.0307(12) 0.0046(10) 0.0011(9) -0.0014(9)
C3 0.0208(10) 0.0173(11) 0.0179(10) 0.0016(8) 0.0007(8) -0.0030(8)
C4 0.0315(11) 0.0209(11) 0.0217(10) -0.0028(9) -0.0025(9) -0.0004(9)
C5 0.0233(10) 0.0157(10) 0.0189(10) -0.0020(8) 0.0033(8) 0.0005(8)
C6 0.0302(11) 0.0227(12) 0.0148(9) -0.0003(8) 0.0027(9) -0.0010(9)
C7 0.0205(10) 0.0185(11) 0.0184(10) 0.0043(8) 0.0022(8) -0.0004(8)
C8 0.0189(10) 0.0166(10) 0.0190(10) 0.0053(8) 0.0020(8) -0.0013(8)
C9 0.0245(11) 0.0202(11) 0.0205(10) 0.0020(8) 0.0004(9) 0.0005(9)
C10 0.0241(11) 0.0278(12) 0.0213(10) 0.0032(9) -0.0038(9) -0.0029(9)
C11 0.0168(10) 0.0284(12) 0.0302(11) 0.0124(9) -0.0001(9) 0.0033(9)
C12 0.0267(11) 0.0193(12) 0.0282(11) 0.0031(9) 0.0092(9) 0.0039(9)
C13 0.0247(11) 0.0184(11) 0.0205(10) 0.0026(8) 0.0003(8) -0.0007(8)
O1 0.0348(9) 0.0319(10) 0.0444(10) -0.0013(8) -0.0058(8) 0.0035(7)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F10 C10 1.354(2) . ?
F11 C11 1.346(2) . ?
F12 C12 1.356(2) . ?
N1 C3 1.519(2) . ?
N1 C5 1.521(2) . ?
N1 C1 1.522(2) . ?
N1 C7 1.532(2) . ?
C1 C2 1.514(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.514(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.520(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.508(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.393(3) . ?
C8 C9 1.397(3) . ?
C9 C10 1.377(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.365(3) . ?
C11 C12 1.377(3) . ?
C12 C13 1.378(3) . ?
C13 H13 0.9500 . ?
O1 H1O1 0.872(17) . ?
O1 H1O2 0.866(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C5 108.10(14) . . ?
C3 N1 C1 109.55(14) . . ?
C5 N1 C1 111.31(14) . . ?
C3 N1 C7 111.21(14) . . ?
C5 N1 C7 109.16(14) . . ?
C1 N1 C7 107.54(14) . . ?
C2 C1 N1 115.21(16) . . ?
C2 C1 H1A 108.5 . . ?
N1 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
N1 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 N1 115.69(16) . . ?
C4 C3 H3A 108.4 . . ?
N1 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
N1 C3 H3B 108.4 . . ?
H3A C3 H3B 107.4 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N1 115.03(16) . . ?
C6 C5 H5A 108.5 . . ?
N1 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
N1 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N1 115.90(15) . . ?
C8 C7 H7A 108.3 . . ?
N1 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
N1 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C13 C8 C9 119.63(18) . . ?
C13 C8 C7 121.64(18) . . ?
C9 C8 C7 118.49(18) . . ?
C10 C9 C8 119.13(19) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
F10 C10 C11 118.19(18) . . ?
F10 C10 C9 119.98(19) . . ?
C11 C10 C9 121.82(19) . . ?
F11 C11 C10 120.96(19) . . ?
F11 C11 C12 120.3(2) . . ?
C10 C11 C12 118.70(19) . . ?
F12 C12 C11 118.11(18) . . ?
F12 C12 C13 120.16(19) . . ?
C11 C12 C13 121.7(2) . . ?
C12 C13 C8 119.00(19) . . ?
C12 C13 H13 120.5 . . ?
C8 C13 H13 120.5 . . ?
H1O1 O1 H1O2 102(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 C2 174.34(16) . . . . ?
C5 N1 C1 C2 54.9(2) . . . . ?
C7 N1 C1 C2 -64.7(2) . . . . ?
C5 N1 C3 C4 171.74(16) . . . . ?
C1 N1 C3 C4 50.3(2) . . . . ?
C7 N1 C3 C4 -68.4(2) . . . . ?
C3 N1 C5 C6 -72.1(2) . . . . ?
C1 N1 C5 C6 48.3(2) . . . . ?
C7 N1 C5 C6 166.83(16) . . . . ?
C3 N1 C7 C8 -51.7(2) . . . . ?
C5 N1 C7 C8 67.5(2) . . . . ?
C1 N1 C7 C8 -171.65(16) . . . . ?
N1 C7 C8 C13 -83.4(2) . . . . ?
N1 C7 C8 C9 102.2(2) . . . . ?
C13 C8 C9 C10 1.1(3) . . . . ?
C7 C8 C9 C10 175.58(17) . . . . ?
C8 C9 C10 F10 -178.49(17) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
F10 C10 C11 F11 0.1(3) . . . . ?
C9 C10 C11 F11 -178.59(18) . . . . ?
F10 C10 C11 C12 177.83(18) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
F11 C11 C12 F12 0.0(3) . . . . ?
C10 C11 C12 F12 -177.73(18) . . . . ?
F11 C11 C12 C13 177.99(18) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
F12 C12 C13 C8 178.96(18) . . . . ?
C11 C12 C13 C8 1.0(3) . . . . ?
C9 C8 C13 C12 -1.7(3) . . . . ?
C7 C8 C13 C12 -175.98(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O1 Br1 0.872(17) 2.522(18) 3.3790(17) 168(2) 3_666
O1 H1O2 Br1 0.866(17) 2.470(17) 3.3356(16) 178(3) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.052

_iucr_refine_instructions_details 
;
TITL mm-303-5 in P 21/c
REM  transformed from space group : P21/a
CELL   0.71073 13.9329  8.3923 12.8666   90.000   94.019   90.000
ZERR   4        0.0003  0.0002  0.0003    0.000    0.001    0.000
LATT    1
SYMM   -X,1/2+Y,1/2-Z
SFAC        C       H       N       O        F       BR
UNIT        52      84       4      4        12       4
L.S.      10
OMIT -3 50.5
OMIT -1 8 1
TEMP  -150
SIZE  0.30 0.20 0.10
EQIV $1 -x+1, -y+1, -z+1
HTAB O1 Br1_$1
HTAB O1 Br1
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.019700    0.531300
FVAR       0.54671
MOLE 1
BR1   6    0.676555    0.529043    0.600229    11.00000    0.02642    0.01928 =
         0.02339   -0.00107   -0.00038    0.00212
F10   5    1.003237    0.332302    0.553359    11.00000    0.03528    0.04484 =
         0.03341   -0.00364   -0.01630    0.00446
F11   5    1.075564    0.096145    0.440051    11.00000    0.02113    0.04199 =
         0.04026    0.01107    0.00028    0.01073
F12   5    0.974898   -0.015067    0.268720    11.00000    0.03979    0.03138 =
         0.03996   -0.00470    0.00467    0.01548
N1    3    0.705289    0.486203    0.234457    11.00000    0.01645    0.01520 =
         0.01660    0.00188    0.00022    0.00080
C1    1    0.604084    0.555219    0.231260    11.00000    0.01612    0.02450 =
         0.02079    0.00124    0.00107    0.00569
AFIX  23
H1A   2    0.593200    0.598910    0.300932    11.00000   -1.20000
H1B   2    0.600120    0.645091    0.181303    11.00000   -1.20000
AFIX   0
C2    1    0.524026    0.438832    0.200773    11.00000    0.01922    0.03411 =
         0.03072    0.00464    0.00113   -0.00140
AFIX  33
H2A   2    0.461881    0.493581    0.200478    11.00000   -1.50000
H2B   2    0.525528    0.350965    0.251028    11.00000   -1.50000
H2C   2    0.532835    0.396590    0.131074    11.00000   -1.50000
AFIX   0
C3    1    0.778369    0.618666    0.255251    11.00000    0.02079    0.01734 =
         0.01791    0.00161    0.00074   -0.00297
AFIX  23
H3A   2    0.842928    0.569905    0.266901    11.00000   -1.20000
H3B   2    0.778949    0.685675    0.191973    11.00000   -1.20000
AFIX   0
C4    1    0.761640    0.725607    0.346972    11.00000    0.03146    0.02086 =
         0.02169   -0.00284   -0.00248   -0.00036
AFIX  33
H4A   2    0.812085    0.807079    0.353648    11.00000   -1.50000
H4B   2    0.763325    0.661720    0.410830    11.00000   -1.50000
H4C   2    0.698678    0.777262    0.335823    11.00000   -1.50000
AFIX   0
C5    1    0.724887    0.407934    0.131480    11.00000    0.02335    0.01568 =
         0.01890   -0.00204    0.00329    0.00045
AFIX  23
H5A   2    0.794291    0.382208    0.132501    11.00000   -1.20000
H5B   2    0.688969    0.306174    0.125688    11.00000   -1.20000
AFIX   0
C6    1    0.697765    0.507538    0.035192    11.00000    0.03023    0.02270 =
         0.01485   -0.00033    0.00274   -0.00097
AFIX  33
H6A   2    0.713071    0.448407   -0.027210    11.00000   -1.50000
H6B   2    0.734054    0.607647    0.038945    11.00000   -1.50000
H6C   2    0.628685    0.530772    0.031767    11.00000   -1.50000
AFIX   0
C7    1    0.713281    0.360657    0.321029    11.00000    0.02046    0.01846 =
         0.01837    0.00428    0.00223   -0.00039
AFIX  23
H7A   2    0.689840    0.408371    0.384905    11.00000   -1.20000
H7B   2    0.669778    0.271151    0.300301    11.00000   -1.20000
AFIX   0
C8    1    0.812548    0.294117    0.347349    11.00000    0.01888    0.01656 =
         0.01896    0.00530    0.00202   -0.00128
C9    1    0.864712    0.349807    0.436722    11.00000    0.02446    0.02020 =
         0.02046    0.00201    0.00040    0.00049
AFIX  43
H9    2    0.839839    0.433105    0.476997    11.00000   -1.20000
AFIX   0
C10   1    0.952630    0.282395    0.465663    11.00000    0.02407    0.02783 =
         0.02134    0.00324   -0.00382   -0.00293
C11   1    0.990402    0.162882    0.409311    11.00000    0.01678    0.02837 =
         0.03016    0.01237   -0.00010    0.00329
C12   1    0.938094    0.107482    0.321945    11.00000    0.02667    0.01927 =
         0.02819    0.00309    0.00915    0.00393
C13   1    0.849393    0.169964    0.290274    11.00000    0.02467    0.01841 =
         0.02053    0.00260    0.00028   -0.00068
AFIX  43
H13   2    0.813883    0.129020    0.230421    11.00000   -1.20000
AFIX   0
MOLE 2
O1    4    0.473217    0.725559    0.534483    11.00000    0.03478    0.03190 =
         0.04438   -0.00126   -0.00580    0.00350
H1O1  2    0.441179    0.660624    0.492086    11.00000   -1.50000
H1O2  2    0.525644    0.672713    0.549988    11.00000   -1.50000
DFIX 0.84 O1 H1O1 O1 H1O2
HKLF   4
 
REM  mm-303-5 in P 21/c
REM R1 =  0.0227 for   2354 Fo > 4sig(Fo)  and  0.0292 for all   2712 data
REM    178 parameters refined using      2 restraints
 
END
 
WGHT      0.0197      0.5318
REM Highest difference peak  0.313,  deepest hole -0.244,  1-sigma level  0.052
Q1    1   0.7165  0.8343  0.3234  11.00000  0.05    0.31
Q2    1   0.7631  0.3176  0.3402  11.00000  0.05    0.26
Q3    1   0.8321  0.3072  0.3976  11.00000  0.05    0.24
Q4    1   0.8337  0.7556  0.3616  11.00000  0.05    0.23
Q5    1   0.6319  0.4890 -0.0021  11.00000  0.05    0.23
Q6    1   0.9778  0.1675  0.3453  11.00000  0.05    0.22
Q7    1   0.7285  0.6754  0.4023  11.00000  0.05    0.21
Q8    1   0.9832  0.2548  0.4168  11.00000  0.05    0.21
Q9    1   0.7168  0.4574  0.0845  11.00000  0.05    0.21
Q10   1   0.6788  0.4001  0.5994  11.00000  0.05    0.21
Q11   1   0.7586  0.4660 -0.0195  11.00000  0.05    0.21
Q12   1   0.9535  0.1119  0.3883  11.00000  0.05    0.20
Q13   1   0.7186  0.4545  0.1867  11.00000  0.05    0.20
Q14   1   0.6577  0.5034  0.2368  11.00000  0.05    0.20
Q15   1   0.9526  0.0540  0.2933  11.00000  0.05    0.20
Q16   1   0.7383  0.5496  0.2500  11.00000  0.05    0.20
Q17   1   0.6937  0.6198  0.0442  11.00000  0.05 #######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-yl-10-5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H16 F5 N2, Br'
_chemical_formula_sum            'C13 H16 Br F5 N2'
_chemical_formula_weight         375.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.9614(3)
_cell_length_b                   18.5641(7)
_cell_length_c                   8.8560(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.771(2)
_cell_angle_gamma                90.00
_cell_volume                     1468.18(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3660
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    2.849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7262
_exptl_absorpt_correction_T_max  0.8946
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5195
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2653
_reflns_number_gt                2002
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0178P)^2^+9.8096P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2653
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1357
_refine_ls_wR_factor_gt          0.1277
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_restrained_S_all      1.192
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.59134(7) 0.24874(4) 0.83553(6) 0.0306(2) Uani 1 1 d . . .
F7 F 0.7501(4) 0.1391(2) 0.1442(4) 0.0338(9) Uani 1 1 d . . .
F8 F 0.9053(4) 0.0369(2) 0.3037(5) 0.0428(11) Uani 1 1 d . . .
F9 F 0.8098(5) -0.0117(2) 0.5689(5) 0.0434(11) Uani 1 1 d . . .
F10 F 0.5578(5) 0.0437(2) 0.6735(4) 0.0417(10) Uani 1 1 d . . .
F11 F 0.3994(4) 0.1445(2) 0.5123(4) 0.0326(9) Uani 1 1 d . . .
N1 N 0.7273(6) 0.3746(3) 0.4770(6) 0.0270(12) Uani 1 1 d . . .
N2 N 0.5325(6) 0.2827(3) 0.2798(6) 0.0223(11) Uani 1 1 d . . .
C1 C 0.7522(7) 0.3673(3) 0.3164(7) 0.0248(14) Uani 1 1 d . . .
H1A H 0.8603 0.3721 0.3030 0.030 Uiso 1 1 calc R . .
H1B H 0.6982 0.4060 0.2575 0.030 Uiso 1 1 calc R . .
C2 C 0.6962(7) 0.2941(3) 0.2585(7) 0.0239(14) Uani 1 1 d . . .
H2A H 0.7117 0.2899 0.1495 0.029 Uiso 1 1 calc R . .
H2B H 0.7556 0.2558 0.3131 0.029 Uiso 1 1 calc R . .
C3 C 0.5079(7) 0.2979(3) 0.4455(6) 0.0241(14) Uani 1 1 d . . .
H3A H 0.3993 0.2962 0.4586 0.029 Uiso 1 1 calc R . .
H3B H 0.5574 0.2598 0.5100 0.029 Uiso 1 1 calc R . .
C4 C 0.5689(7) 0.3703(4) 0.4970(7) 0.0276(15) Uani 1 1 d . . .
H4A H 0.5150 0.4089 0.4376 0.033 Uiso 1 1 calc R . .
H4B H 0.5526 0.3776 0.6052 0.033 Uiso 1 1 calc R . .
C5 C 0.4874(7) 0.2060(3) 0.2390(7) 0.0257(15) Uani 1 1 d . . .
H5A H 0.3799 0.1999 0.2542 0.031 Uiso 1 1 calc R . .
H5B H 0.4992 0.1985 0.1300 0.031 Uiso 1 1 calc R . .
C6 C 0.5741(7) 0.1493(3) 0.3273(7) 0.0223(13) Uani 1 1 d . . .
C7 C 0.7030(7) 0.1182(3) 0.2773(7) 0.0243(14) Uani 1 1 d . . .
C8 C 0.7813(7) 0.0651(4) 0.3556(8) 0.0297(15) Uani 1 1 d . . .
C9 C 0.7335(7) 0.0403(3) 0.4913(8) 0.0293(15) Uani 1 1 d . . .
C10 C 0.6069(8) 0.0686(3) 0.5433(7) 0.0288(15) Uani 1 1 d . . .
C11 C 0.5275(7) 0.1216(3) 0.4611(7) 0.0257(14) Uani 1 1 d . . .
C12 C 0.7951(8) 0.4415(4) 0.5408(8) 0.0380(18) Uani 1 1 d . . .
H12A H 0.7757 0.4455 0.6477 0.057 Uiso 1 1 calc R . .
H12B H 0.7512 0.4830 0.4848 0.057 Uiso 1 1 calc R . .
H12C H 0.9034 0.4406 0.5321 0.057 Uiso 1 1 calc R . .
C13 C 0.4359(7) 0.3308(4) 0.1775(7) 0.0298(15) Uani 1 1 d . . .
H13A H 0.3305 0.3228 0.1943 0.045 Uiso 1 1 calc R . .
H13B H 0.4519 0.3200 0.0717 0.045 Uiso 1 1 calc R . .
H13C H 0.4621 0.3812 0.1993 0.045 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0212(3) 0.0516(4) 0.0184(3) 0.0039(3) -0.0009(2) -0.0066(3)
F7 0.035(2) 0.035(2) 0.033(2) 0.0021(18) 0.0132(17) 0.0040(18)
F8 0.028(2) 0.041(2) 0.061(3) 0.000(2) 0.0078(19) 0.0121(19)
F9 0.044(3) 0.033(2) 0.051(3) 0.014(2) -0.011(2) 0.0070(19)
F10 0.059(3) 0.035(2) 0.030(2) 0.0113(18) 0.0015(19) -0.002(2)
F11 0.032(2) 0.035(2) 0.032(2) 0.0046(17) 0.0112(17) 0.0024(17)
N1 0.028(3) 0.027(3) 0.026(3) -0.006(2) 0.003(2) -0.001(2)
N2 0.021(3) 0.024(3) 0.023(3) -0.002(2) 0.008(2) 0.002(2)
C1 0.029(3) 0.022(3) 0.024(3) 0.000(3) 0.008(3) -0.003(3)
C2 0.020(3) 0.028(4) 0.023(3) 0.002(3) 0.000(3) 0.001(3)
C3 0.027(3) 0.031(4) 0.015(3) 0.005(3) 0.005(3) -0.001(3)
C4 0.031(4) 0.030(4) 0.023(3) -0.006(3) 0.010(3) -0.002(3)
C5 0.028(4) 0.026(4) 0.024(3) 0.006(3) 0.011(3) 0.003(3)
C6 0.021(3) 0.024(3) 0.021(3) -0.002(3) -0.002(2) 0.003(3)
C7 0.025(3) 0.025(3) 0.023(3) -0.002(3) 0.005(3) -0.001(3)
C8 0.024(3) 0.025(4) 0.040(4) -0.006(3) 0.002(3) 0.004(3)
C9 0.028(4) 0.021(3) 0.037(4) 0.003(3) -0.009(3) 0.007(3)
C10 0.044(4) 0.023(3) 0.018(3) 0.004(3) -0.004(3) -0.006(3)
C11 0.027(3) 0.025(3) 0.026(3) -0.001(3) 0.005(3) 0.002(3)
C12 0.042(4) 0.031(4) 0.042(4) -0.013(3) 0.004(3) -0.007(3)
C13 0.029(4) 0.035(4) 0.024(3) 0.006(3) -0.005(3) 0.004(3)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F7 C7 1.341(7) . ?
F8 C8 1.343(7) . ?
F9 C9 1.341(7) . ?
F10 C10 1.349(7) . ?
F11 C11 1.338(7) . ?
N1 C4 1.448(8) . ?
N1 C1 1.464(8) . ?
N1 C12 1.476(8) . ?
N2 C13 1.496(8) . ?
N2 C2 1.509(8) . ?
N2 C5 1.516(8) . ?
N2 C3 1.528(7) . ?
C1 C2 1.524(8) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.507(9) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.491(9) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.388(9) . ?
C6 C7 1.396(9) . ?
C7 C8 1.365(9) . ?
C8 C9 1.387(10) . ?
C9 C10 1.364(10) . ?
C10 C11 1.385(9) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C1 110.1(5) . . ?
C4 N1 C12 112.1(5) . . ?
C1 N1 C12 111.0(5) . . ?
C13 N2 C2 111.1(5) . . ?
C13 N2 C5 106.7(5) . . ?
C2 N2 C5 110.1(5) . . ?
C13 N2 C3 110.5(5) . . ?
C2 N2 C3 108.3(5) . . ?
C5 N2 C3 110.2(5) . . ?
N1 C1 C2 109.6(5) . . ?
N1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
N2 C2 C1 112.3(5) . . ?
N2 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
N2 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 N2 112.2(5) . . ?
C4 C3 H3A 109.2 . . ?
N2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
N2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
N1 C4 C3 110.2(5) . . ?
N1 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
N1 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C6 C5 N2 114.9(5) . . ?
C6 C5 H5A 108.5 . . ?
N2 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
N2 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C11 C6 C7 115.7(6) . . ?
C11 C6 C5 121.9(6) . . ?
C7 C6 C5 122.3(6) . . ?
F7 C7 C8 118.0(6) . . ?
F7 C7 C6 119.2(6) . . ?
C8 C7 C6 122.8(6) . . ?
F8 C8 C7 120.8(6) . . ?
F8 C8 C9 119.4(6) . . ?
C7 C8 C9 119.8(6) . . ?
F9 C9 C10 120.5(6) . . ?
F9 C9 C8 120.1(6) . . ?
C10 C9 C8 119.4(6) . . ?
F10 C10 C9 119.8(6) . . ?
F10 C10 C11 120.2(6) . . ?
C9 C10 C11 120.1(6) . . ?
F11 C11 C10 117.8(6) . . ?
F11 C11 C6 119.9(6) . . ?
C10 C11 C6 122.3(6) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 -61.5(6) . . . . ?
C12 N1 C1 C2 173.8(5) . . . . ?
C13 N2 C2 C1 69.1(6) . . . . ?
C5 N2 C2 C1 -172.9(5) . . . . ?
C3 N2 C2 C1 -52.4(6) . . . . ?
N1 C1 C2 N2 57.8(7) . . . . ?
C13 N2 C3 C4 -69.5(6) . . . . ?
C2 N2 C3 C4 52.4(6) . . . . ?
C5 N2 C3 C4 172.9(5) . . . . ?
C1 N1 C4 C3 62.0(6) . . . . ?
C12 N1 C4 C3 -174.0(5) . . . . ?
N2 C3 C4 N1 -58.1(7) . . . . ?
C13 N2 C5 C6 178.7(5) . . . . ?
C2 N2 C5 C6 58.1(6) . . . . ?
C3 N2 C5 C6 -61.3(6) . . . . ?
N2 C5 C6 C11 91.1(7) . . . . ?
N2 C5 C6 C7 -92.0(7) . . . . ?
C11 C6 C7 F7 176.1(6) . . . . ?
C5 C6 C7 F7 -1.0(9) . . . . ?
C11 C6 C7 C8 -1.4(9) . . . . ?
C5 C6 C7 C8 -178.5(6) . . . . ?
F7 C7 C8 F8 2.8(9) . . . . ?
C6 C7 C8 F8 -179.7(6) . . . . ?
F7 C7 C8 C9 -177.9(6) . . . . ?
C6 C7 C8 C9 -0.4(10) . . . . ?
F8 C8 C9 F9 -0.6(10) . . . . ?
C7 C8 C9 F9 -179.9(6) . . . . ?
F8 C8 C9 C10 -179.5(6) . . . . ?
C7 C8 C9 C10 1.2(10) . . . . ?
F9 C9 C10 F10 -0.3(9) . . . . ?
C8 C9 C10 F10 178.6(6) . . . . ?
F9 C9 C10 C11 -179.0(6) . . . . ?
C8 C9 C10 C11 -0.2(10) . . . . ?
F10 C10 C11 F11 -2.5(9) . . . . ?
C9 C10 C11 F11 176.2(6) . . . . ?
F10 C10 C11 C6 179.5(6) . . . . ?
C9 C10 C11 C6 -1.8(10) . . . . ?
C7 C6 C11 F11 -175.5(6) . . . . ?
C5 C6 C11 F11 1.6(9) . . . . ?
C7 C6 C11 C10 2.5(9) . . . . ?
C5 C6 C11 C10 179.6(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.108

_iucr_refine_instructions_details 
;
TITL mm-yl-10-5 in P 21/n
CELL   0.71073   8.9614  18.5641   8.8560  90.000  94.771  90.000
ZERR     4       0.0003   0.0007   0.0003   0.000   0.002   0.000
LATT  1
SYMM 1/2-X,1/2+Y,1/2-Z
SFAC        C       H       N       F       BR
UNIT        52      64      8       20      4
L.S.      10
OMIT -3 50.5
OMIT 0 2 0
OMIT 3 6 2
OMIT 2 7 3
OMIT 0 1 1
OMIT 1 3 0
OMIT 2 8 3
OMIT -4 2 1
OMIT 1 3 2
TEMP  -150
SIZE  0.12 0.07 0.04
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.017800    9.809600
FVAR       0.43830
BR1   5    0.591343    0.248736    0.835528    11.00000    0.02121    0.05158 =
         0.01845    0.00388   -0.00085   -0.00660
F7    4    0.750134    0.139082    0.144221    11.00000    0.03524    0.03482 =
         0.03310    0.00212    0.01320    0.00405
F8    4    0.905306    0.036901    0.303715    11.00000    0.02760    0.04085 =
         0.06067    0.00049    0.00784    0.01212
F9    4    0.809839   -0.011744    0.568876    11.00000    0.04377    0.03319 =
         0.05070    0.01376   -0.01149    0.00704
F10   4    0.557824    0.043666    0.673503    11.00000    0.05908    0.03522 =
         0.03048    0.01127    0.00148   -0.00219
F11   4    0.399423    0.144537    0.512328    11.00000    0.03237    0.03526 =
         0.03161    0.00458    0.01118    0.00239
N1    3    0.727345    0.374552    0.477016    11.00000    0.02813    0.02701 =
         0.02608   -0.00574    0.00345   -0.00104
N2    3    0.532507    0.282737    0.279849    11.00000    0.02088    0.02386 =
         0.02329   -0.00181    0.00781    0.00172
C1    1    0.752197    0.367316    0.316369    11.00000    0.02885    0.02234 =
         0.02428   -0.00050    0.00797   -0.00331
AFIX  23
H1A   2    0.860334    0.372075    0.302966    11.00000   -1.20000
H1B   2    0.698201    0.406019    0.257511    11.00000   -1.20000
AFIX   0
C2    1    0.696177    0.294061    0.258510    11.00000    0.02042    0.02846 =
         0.02259    0.00165    0.00017    0.00102
AFIX  23
H2A   2    0.711681    0.289933    0.149464    11.00000   -1.20000
H2B   2    0.755634    0.255756    0.313059    11.00000   -1.20000
AFIX   0
C3    1    0.507881    0.297917    0.445491    11.00000    0.02652    0.03110 =
         0.01521    0.00450    0.00490   -0.00060
AFIX  23
H3A   2    0.399295    0.296202    0.458582    11.00000   -1.20000
H3B   2    0.557372    0.259841    0.509951    11.00000   -1.20000
AFIX   0
C4    1    0.568870    0.370323    0.496997    11.00000    0.03107    0.03007 =
         0.02280   -0.00556    0.00959   -0.00214
AFIX  23
H4A   2    0.515018    0.408888    0.437578    11.00000   -1.20000
H4B   2    0.552621    0.377594    0.605155    11.00000   -1.20000
AFIX   0
C5    1    0.487377    0.206014    0.238977    11.00000    0.02795    0.02644 =
         0.02427    0.00609    0.01077    0.00283
AFIX  23
H5A   2    0.379915    0.199922    0.254240    11.00000   -1.20000
H5B   2    0.499202    0.198456    0.129957    11.00000   -1.20000
AFIX   0
C6    1    0.574062    0.149258    0.327276    11.00000    0.02127    0.02415 =
         0.02077   -0.00242   -0.00234    0.00275
C7    1    0.703048    0.118197    0.277278    11.00000    0.02500    0.02536 =
         0.02304   -0.00171    0.00491   -0.00123
C8    1    0.781318    0.065084    0.355571    11.00000    0.02385    0.02493 =
         0.04004   -0.00611    0.00160    0.00407
C9    1    0.733486    0.040334    0.491265    11.00000    0.02832    0.02113 =
         0.03660    0.00286   -0.00891    0.00698
C10   1    0.606908    0.068552    0.543298    11.00000    0.04404    0.02304 =
         0.01814    0.00419   -0.00430   -0.00563
C11   1    0.527470    0.121557    0.461102    11.00000    0.02712    0.02457 =
         0.02607   -0.00099    0.00546    0.00213
C12   1    0.795115    0.441548    0.540781    11.00000    0.04205    0.03055 =
         0.04164   -0.01347    0.00442   -0.00706
AFIX  33
H12A  2    0.775724    0.445547    0.647743    11.00000   -1.50000
H12B  2    0.751219    0.483010    0.484817    11.00000   -1.50000
H12C  2    0.903411    0.440579    0.532128    11.00000   -1.50000
AFIX   0
C13   1    0.435941    0.330841    0.177459    11.00000    0.02939    0.03500 =
         0.02389    0.00555   -0.00483    0.00372
AFIX  33
H13A  2    0.330516    0.322793    0.194257    11.00000   -1.50000
H13B  2    0.451949    0.319999    0.071715    11.00000   -1.50000
H13C  2    0.462100    0.381244    0.199330    11.00000   -1.50000
HKLF   4
 
REM  mm-yl-10-5 in P 21/n
REM R1 =  0.0583 for   2002 Fo > 4sig(Fo)  and  0.0838 for all   2653 data
REM    190 parameters refined using      0 restraints
 
END
 
WGHT      0.0178      9.8082
REM Highest difference peak  0.684,  deepest hole -0.385,  1-sigma level  0.108
Q1    1   0.7538  0.3580  0.1459  11.00000  0.05    0.68
Q2    1   0.3926  0.3595  0.4874  11.00000  0.05    0.65
Q3    1   0.5519  0.4591  0.6560  11.00000  0.05    0.63
Q4    1   0.7401  0.1257  0.4812  11.00000  0.05    0.60
Q5    1   0.9296  0.4590  0.3099  11.00000  0.05    0.59
Q6    1   0.7109  0.1948  0.2653  11.00000  0.05    0.50
Q7    1   0.7036  0.3885  0.2455  11.00000  0.05    0.44
Q8    1   0.8051  0.4334  0.3524  11.00000  0.05    0.43
Q9    1   0.5164  0.2117  0.4685  11.00000  0.05    0.42
Q10   1   0.5022  0.3920  0.4569  11.00000  0.05    0.41
Q11   1   0.5533  0.2518  0.8724  11.00000  0.05    0.40
Q12   1   0.6167  0.3176  0.0586  11.00000  0.05    0.39
Q13   1   0.5643  0.2224  0.7747  11.00000  0.05    0.37
Q14   1   0.8455  0.4988  0.5200  11.00000  0.05    0.36
Q15   1   0.4510  0.1543  0.1833  11.00000  0.05    0.36
Q16   1   0.5802  0.3607  0.3103  11.00000  0.05    0.35
Q17   1   0.5409  0.2376  0.2962  11.00000  0.05    0.34
Q18   1   0.5650  0.1549  0.6679  11.00000  0.05    0.34
Q19   1   0.7715  0.5150  0.5635  11.00000  0.05    0.34
Q20   1   0.4848  0.2898  0.2171  11.00000  0.05    0.34
Q21   1   0.6136  0.2672  0.8294  11.00000  0.05    0.34
Q22   1   0.8988  0.4338  0.4987  11.00000  0.05    0.32
Q23   1   0.2208  0.2664  0.0981  11.00000  0.05    0.32
Q24   1   0.7493  0.0699  0.5779  11.00000  0.05    0.31
Q25   1   0.5419  0.0612  0.4742  11.00000  0.05    0.30
;
_database_code_depnum_ccdc_archive 'CCDC 1005278'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-tb-1-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H13 F5 N O, Br'
_chemical_formula_sum            'C11 H13 Br F5 N O'
_chemical_formula_weight         350.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.86600(10)
_cell_length_b                   14.2952(3)
_cell_length_c                   26.3661(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.4170(10)
_cell_angle_gamma                90.00
_cell_volume                     2580.17(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6543
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_absorpt_coefficient_mu    3.238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3725
_exptl_absorpt_correction_T_max  0.5104
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9105
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         25.25
_reflns_number_total             4666
_reflns_number_gt                4085
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0199P)^2^+2.3756P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4666
_refine_ls_number_parameters     367
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0245
_refine_ls_wR_factor_ref         0.0568
_refine_ls_wR_factor_gt          0.0540
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.74343(3) 0.166732(16) 0.458304(8) 0.02141(7) Uani 1 1 d . . .
Br2 Br 0.48639(3) 0.376145(17) 0.223537(9) 0.02687(7) Uani 1 1 d . . .
F5 F 0.8151(2) 0.19087(10) -0.01213(6) 0.0386(4) Uani 1 1 d . . .
F6 F 0.5523(2) 0.08197(10) -0.06363(5) 0.0333(3) Uani 1 1 d . A .
F7 F 0.2041(2) 0.04401(10) -0.02503(5) 0.0328(3) Uani 1 1 d . . .
F8 F 0.1252(2) 0.11534(11) 0.06630(6) 0.0358(4) Uani 1 1 d . A .
F9 F 0.3864(2) 0.22622(11) 0.11793(5) 0.0424(4) Uani 1 1 d . . .
O2 O 1.0626(2) 0.32830(12) 0.16079(7) 0.0309(4) Uani 1 1 d D . .
H2 H 1.172(3) 0.334(2) 0.1751(11) 0.046 Uiso 1 1 d D . .
N1 N 0.7419(3) 0.37928(14) 0.07060(8) 0.0335(5) Uani 1 1 d . . .
C1 C 0.9332(6) 0.4296(3) 0.09294(17) 0.0235(9) Uani 0.60 1 d P A 1
H1A H 1.0460 0.4046 0.0760 0.028 Uiso 0.60 1 calc PR A 1
H1B H 0.9229 0.4972 0.0853 0.028 Uiso 0.60 1 calc PR A 1
C2 C 0.9699(7) 0.4167(3) 0.14965(17) 0.0264(9) Uani 0.60 1 d P A 1
H2A H 1.0544 0.4678 0.1639 0.032 Uiso 0.60 1 calc PR A 1
H2B H 0.8444 0.4195 0.1657 0.032 Uiso 0.60 1 calc PR A 1
C1B C 0.8457(9) 0.4356(4) 0.1168(2) 0.0224(13) Uani 0.40 1 d P A 2
H1B1 H 0.8396 0.5036 0.1096 0.027 Uiso 0.40 1 calc PR A 2
H1B2 H 0.7790 0.4235 0.1481 0.027 Uiso 0.40 1 calc PR A 2
C2B C 1.0558(9) 0.4042(4) 0.1239(3) 0.0256(13) Uani 0.40 1 d P A 2
H2B1 H 1.1013 0.3821 0.0912 0.031 Uiso 0.40 1 calc PR A 2
H2B2 H 1.1406 0.4565 0.1366 0.031 Uiso 0.40 1 calc PR A 2
C3 C 0.7564(4) 0.27549(17) 0.08377(11) 0.0418(8) Uani 1 1 d . A .
H3A H 0.8889 0.2531 0.0774 0.050 Uiso 1 1 calc R . .
H3B H 0.7404 0.2678 0.1205 0.050 Uiso 1 1 calc R . .
C4 C 0.6078(3) 0.21477(16) 0.05417(9) 0.0271(5) Uani 1 1 d . . .
C5 C 0.6444(3) 0.17460(16) 0.00820(9) 0.0254(5) Uani 1 1 d . A .
C6 C 0.5113(3) 0.11787(16) -0.01850(9) 0.0233(5) Uani 1 1 d . . .
C7 C 0.3356(3) 0.09824(16) 0.00076(8) 0.0218(5) Uani 1 1 d . A .
C8 C 0.2958(3) 0.13469(16) 0.04711(9) 0.0231(5) Uani 1 1 d . . .
C9 C 0.4310(4) 0.19188(16) 0.07287(9) 0.0269(5) Uani 1 1 d . A .
C10 C 0.7672(4) 0.39593(18) 0.01565(11) 0.0345(6) Uani 1 1 d . A .
H10A H 0.8944 0.3717 0.0073 0.052 Uiso 1 1 calc R . .
H10B H 0.7606 0.4632 0.0086 0.052 Uiso 1 1 calc R . .
H10C H 0.6631 0.3638 -0.0051 0.052 Uiso 1 1 calc R . .
C11 C 0.5486(4) 0.41758(19) 0.08171(10) 0.0398(7) Uani 1 1 d . A .
H11A H 0.5285 0.4079 0.1177 0.060 Uiso 1 1 calc R . .
H11B H 0.4454 0.3854 0.0607 0.060 Uiso 1 1 calc R . .
H11C H 0.5442 0.4847 0.0741 0.060 Uiso 1 1 calc R . .
F5A F -0.3071(2) 0.15694(10) 0.18780(5) 0.0343(3) Uani 1 1 d . . .
F6A F -0.2519(3) 0.01155(12) 0.12691(6) 0.0481(4) Uani 1 1 d . . .
F7A F 0.0996(3) -0.07706(11) 0.13120(6) 0.0506(4) Uani 1 1 d . . .
F8A F 0.3949(2) -0.01729(12) 0.19856(8) 0.0563(5) Uani 1 1 d . . .
F9A F 0.3366(2) 0.12499(11) 0.26133(7) 0.0422(4) Uani 1 1 d . . .
O2A O 0.3440(3) 0.12572(13) 0.38914(7) 0.0376(5) Uani 1 1 d D . .
H2AO H 0.441(4) 0.148(2) 0.4047(11) 0.056 Uiso 1 1 d D . .
N1A N -0.0907(2) 0.21029(13) 0.31078(7) 0.0177(4) Uani 1 1 d . . .
C1A C 0.0458(3) 0.15093(15) 0.34488(8) 0.0200(5) Uani 1 1 d . . .
H1A1 H 0.0825 0.0951 0.3255 0.024 Uiso 1 1 calc R . .
H1A2 H -0.0255 0.1288 0.3738 0.024 Uiso 1 1 calc R . .
C2A C 0.2315(3) 0.19971(17) 0.36583(9) 0.0275(5) Uani 1 1 d . . .
H2A1 H 0.3001 0.2291 0.3382 0.033 Uiso 1 1 calc R . .
H2A2 H 0.2029 0.2482 0.3910 0.033 Uiso 1 1 calc R . .
C3A C -0.0139(3) 0.23181(15) 0.25914(8) 0.0201(5) Uani 1 1 d . . .
H3A1 H -0.1063 0.2749 0.2403 0.024 Uiso 1 1 calc R . .
H3A2 H 0.1128 0.2646 0.2648 0.024 Uiso 1 1 calc R . .
C4A C 0.0136(3) 0.14708(16) 0.22679(8) 0.0205(5) Uani 1 1 d . . .
C5A C -0.1321(3) 0.11470(16) 0.19152(8) 0.0242(5) Uani 1 1 d . . .
C6A C -0.1046(4) 0.04100(17) 0.15956(9) 0.0310(6) Uani 1 1 d . . .
C7A C 0.0728(4) -0.00327(17) 0.16140(9) 0.0328(6) Uani 1 1 d . . .
C8A C 0.2224(4) 0.02678(18) 0.19531(11) 0.0342(6) Uani 1 1 d . . .
C9A C 0.1903(3) 0.10039(17) 0.22711(9) 0.0271(5) Uani 1 1 d . . .
C10A C -0.2809(3) 0.15890(17) 0.30269(9) 0.0241(5) Uani 1 1 d . . .
H10D H -0.2592 0.0986 0.2864 0.036 Uiso 1 1 calc R . .
H10E H -0.3731 0.1962 0.2808 0.036 Uiso 1 1 calc R . .
H10F H -0.3347 0.1483 0.3356 0.036 Uiso 1 1 calc R . .
C11A C -0.1308(3) 0.30210(16) 0.33583(9) 0.0247(5) Uani 1 1 d . . .
H11D H -0.0086 0.3373 0.3416 0.037 Uiso 1 1 calc R . .
H11E H -0.1856 0.2905 0.3685 0.037 Uiso 1 1 calc R . .
H11F H -0.2242 0.3383 0.3137 0.037 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02020(12) 0.02162(12) 0.02182(12) -0.00252(9) -0.00221(8) -0.00122(9)
Br2 0.02609(13) 0.03116(14) 0.02244(12) -0.00504(10) -0.00411(9) 0.00631(10)
F5 0.0262(8) 0.0315(8) 0.0583(10) 0.0084(7) 0.0052(7) -0.0007(6)
F6 0.0487(9) 0.0283(8) 0.0236(7) -0.0020(6) 0.0076(6) 0.0041(7)
F7 0.0362(8) 0.0277(8) 0.0329(8) -0.0048(6) -0.0086(6) -0.0079(6)
F8 0.0348(8) 0.0396(9) 0.0341(8) 0.0074(7) 0.0096(6) 0.0025(7)
F9 0.0715(11) 0.0348(9) 0.0202(7) -0.0072(6) -0.0002(7) 0.0113(8)
O2 0.0285(9) 0.0283(9) 0.0336(10) 0.0077(8) -0.0131(8) -0.0023(8)
N1 0.0405(12) 0.0156(10) 0.0400(13) 0.0019(9) -0.0244(10) 0.0001(9)
C1 0.022(2) 0.019(2) 0.028(2) 0.0028(18) -0.005(2) -0.0063(17)
C2 0.029(2) 0.024(2) 0.026(2) -0.0031(18) -0.008(2) -0.0026(18)
C1B 0.022(3) 0.023(3) 0.022(3) -0.002(3) 0.000(3) -0.006(3)
C2B 0.027(3) 0.025(3) 0.024(3) 0.006(3) -0.002(3) -0.004(3)
C3 0.0529(17) 0.0147(13) 0.0521(18) 0.0048(12) -0.0333(14) -0.0033(12)
C4 0.0322(13) 0.0164(12) 0.0302(13) 0.0033(10) -0.0139(10) 0.0012(10)
C5 0.0241(12) 0.0180(12) 0.0336(13) 0.0064(10) -0.0018(10) 0.0035(9)
C6 0.0325(13) 0.0167(12) 0.0205(12) 0.0000(9) 0.0008(10) 0.0046(10)
C7 0.0277(12) 0.0147(11) 0.0216(12) 0.0001(9) -0.0064(9) -0.0014(9)
C8 0.0254(12) 0.0198(12) 0.0240(12) 0.0046(10) 0.0008(10) 0.0031(9)
C9 0.0442(15) 0.0184(12) 0.0170(12) -0.0009(9) -0.0057(10) 0.0079(11)
C10 0.0284(13) 0.0235(14) 0.0530(18) 0.0049(12) 0.0120(12) 0.0016(11)
C11 0.074(2) 0.0218(13) 0.0247(14) -0.0004(11) 0.0141(13) 0.0048(14)
F5A 0.0391(8) 0.0335(8) 0.0278(8) -0.0034(6) -0.0143(6) 0.0115(7)
F6A 0.0735(12) 0.0417(10) 0.0264(8) -0.0120(7) -0.0142(8) 0.0011(8)
F7A 0.0828(13) 0.0306(9) 0.0413(10) -0.0143(7) 0.0234(9) 0.0033(8)
F8A 0.0381(9) 0.0468(11) 0.0873(14) -0.0170(10) 0.0259(9) 0.0107(8)
F9A 0.0176(7) 0.0446(10) 0.0645(11) -0.0165(8) 0.0041(7) -0.0024(6)
O2A 0.0326(10) 0.0312(10) 0.0452(11) -0.0058(9) -0.0223(9) 0.0097(8)
N1A 0.0166(9) 0.0181(9) 0.0183(9) 0.0004(8) -0.0003(7) 0.0003(7)
C1A 0.0209(11) 0.0180(12) 0.0203(11) 0.0012(9) -0.0036(9) 0.0029(9)
C2A 0.0237(12) 0.0265(13) 0.0303(13) -0.0055(11) -0.0101(10) 0.0034(10)
C3A 0.0224(11) 0.0181(11) 0.0201(11) 0.0013(9) 0.0039(9) -0.0017(9)
C4A 0.0251(12) 0.0174(11) 0.0198(11) 0.0029(9) 0.0063(9) -0.0019(9)
C5A 0.0342(13) 0.0216(12) 0.0170(11) 0.0038(9) 0.0020(10) 0.0029(10)
C6A 0.0511(16) 0.0236(13) 0.0179(12) 0.0000(10) -0.0002(11) -0.0018(12)
C7A 0.0573(17) 0.0182(12) 0.0255(13) -0.0034(10) 0.0191(12) -0.0013(12)
C8A 0.0336(14) 0.0259(14) 0.0461(16) -0.0010(12) 0.0218(12) 0.0030(11)
C9A 0.0236(12) 0.0254(13) 0.0333(14) -0.0021(11) 0.0094(10) -0.0058(10)
C10A 0.0152(11) 0.0328(14) 0.0242(12) 0.0015(10) 0.0007(9) -0.0042(10)
C11A 0.0297(13) 0.0208(12) 0.0231(12) -0.0031(10) -0.0008(10) 0.0062(10)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F5 C5 1.346(3) . ?
F6 C6 1.345(3) . ?
F7 C7 1.335(2) . ?
F8 C8 1.340(3) . ?
F9 C9 1.342(3) . ?
O2 C2 1.435(4) . ?
O2 C2B 1.455(6) . ?
O2 H2 0.817(17) . ?
N1 C11 1.486(4) . ?
N1 C10 1.491(4) . ?
N1 C3 1.525(3) . ?
N1 C1 1.571(4) . ?
N1 C1B 1.582(6) . ?
C1 C2 1.509(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C1B C2B 1.509(9) . ?
C1B H1B1 0.9900 . ?
C1B H1B2 0.9900 . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C3 C4 1.511(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.382(3) . ?
C4 C9 1.384(4) . ?
C5 C6 1.375(3) . ?
C6 C7 1.374(3) . ?
C7 C8 1.375(3) . ?
C8 C9 1.377(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
F5A C5A 1.342(3) . ?
F6A C6A 1.344(3) . ?
F7A C7A 1.343(3) . ?
F8A C8A 1.339(3) . ?
F9A C9A 1.345(3) . ?
O2A C2A 1.421(3) . ?
O2A H2AO 0.820(18) . ?
N1A C10A 1.499(3) . ?
N1A C11A 1.504(3) . ?
N1A C1A 1.509(3) . ?
N1A C3A 1.529(3) . ?
C1A C2A 1.519(3) . ?
C1A H1A1 0.9900 . ?
C1A H1A2 0.9900 . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3A C4A 1.502(3) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4A C9A 1.384(3) . ?
C4A C5A 1.392(3) . ?
C5A C6A 1.371(3) . ?
C6A C7A 1.370(4) . ?
C7A C8A 1.377(4) . ?
C8A C9A 1.374(4) . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 H2 113(2) . . ?
C2B O2 H2 103(2) . . ?
C11 N1 C10 107.76(18) . . ?
C11 N1 C3 110.9(2) . . ?
C10 N1 C3 111.5(2) . . ?
C11 N1 C1 119.4(3) . . ?
C10 N1 C1 97.7(2) . . ?
C3 N1 C1 108.8(2) . . ?
C11 N1 C1B 91.0(3) . . ?
C10 N1 C1B 125.9(3) . . ?
C3 N1 C1B 107.6(3) . . ?
C2 C1 N1 112.8(4) . . ?
C2 C1 H1A 109.0 . . ?
N1 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
N1 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
O2 C2 C1 110.4(4) . . ?
O2 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
O2 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C2B C1B N1 108.3(5) . . ?
C2B C1B H1B1 110.0 . . ?
N1 C1B H1B1 110.0 . . ?
C2B C1B H1B2 110.0 . . ?
N1 C1B H1B2 110.0 . . ?
H1B1 C1B H1B2 108.4 . . ?
O2 C2B C1B 106.7(5) . . ?
O2 C2B H2B1 110.4 . . ?
C1B C2B H2B1 110.4 . . ?
O2 C2B H2B2 110.4 . . ?
C1B C2B H2B2 110.4 . . ?
H2B1 C2B H2B2 108.6 . . ?
C4 C3 N1 114.31(19) . . ?
C4 C3 H3A 108.7 . . ?
N1 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
N1 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C5 C4 C9 116.0(2) . . ?
C5 C4 C3 122.0(2) . . ?
C9 C4 C3 121.9(2) . . ?
F5 C5 C6 117.6(2) . . ?
F5 C5 C4 120.0(2) . . ?
C6 C5 C4 122.4(2) . . ?
F6 C6 C7 119.9(2) . . ?
F6 C6 C5 120.1(2) . . ?
C7 C6 C5 120.0(2) . . ?
F7 C7 C6 120.6(2) . . ?
F7 C7 C8 120.0(2) . . ?
C6 C7 C8 119.4(2) . . ?
F8 C8 C7 119.8(2) . . ?
F8 C8 C9 120.8(2) . . ?
C7 C8 C9 119.4(2) . . ?
F9 C9 C8 117.6(2) . . ?
F9 C9 C4 119.7(2) . . ?
C8 C9 C4 122.8(2) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2A O2A H2AO 109(2) . . ?
C10A N1A C11A 107.67(17) . . ?
C10A N1A C1A 107.66(17) . . ?
C11A N1A C1A 110.81(16) . . ?
C10A N1A C3A 109.17(16) . . ?
C11A N1A C3A 107.62(17) . . ?
C1A N1A C3A 113.75(16) . . ?
N1A C1A C2A 115.09(18) . . ?
N1A C1A H1A1 108.5 . . ?
C2A C1A H1A1 108.5 . . ?
N1A C1A H1A2 108.5 . . ?
C2A C1A H1A2 108.5 . . ?
H1A1 C1A H1A2 107.5 . . ?
O2A C2A C1A 103.22(19) . . ?
O2A C2A H2A1 111.1 . . ?
C1A C2A H2A1 111.1 . . ?
O2A C2A H2A2 111.1 . . ?
C1A C2A H2A2 111.1 . . ?
H2A1 C2A H2A2 109.1 . . ?
C4A C3A N1A 114.25(17) . . ?
C4A C3A H3A1 108.7 . . ?
N1A C3A H3A1 108.7 . . ?
C4A C3A H3A2 108.7 . . ?
N1A C3A H3A2 108.7 . . ?
H3A1 C3A H3A2 107.6 . . ?
C9A C4A C5A 115.4(2) . . ?
C9A C4A C3A 122.3(2) . . ?
C5A C4A C3A 122.2(2) . . ?
F5A C5A C6A 117.8(2) . . ?
F5A C5A C4A 119.5(2) . . ?
C6A C5A C4A 122.7(2) . . ?
F6A C6A C7A 120.1(2) . . ?
F6A C6A C5A 120.1(2) . . ?
C7A C6A C5A 119.8(2) . . ?
F7A C7A C6A 120.3(2) . . ?
F7A C7A C8A 120.0(2) . . ?
C6A C7A C8A 119.7(2) . . ?
F8A C8A C9A 120.3(2) . . ?
F8A C8A C7A 120.5(2) . . ?
C9A C8A C7A 119.2(2) . . ?
F9A C9A C8A 117.6(2) . . ?
F9A C9A C4A 119.2(2) . . ?
C8A C9A C4A 123.2(2) . . ?
N1A C10A H10D 109.5 . . ?
N1A C10A H10E 109.5 . . ?
H10D C10A H10E 109.5 . . ?
N1A C10A H10F 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
N1A C11A H11D 109.5 . . ?
N1A C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
N1A C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C1 C2 71.4(4) . . . . ?
C10 N1 C1 C2 -173.1(3) . . . . ?
C3 N1 C1 C2 -57.3(4) . . . . ?
C1B N1 C1 C2 36.5(5) . . . . ?
C2B O2 C2 C1 35.3(5) . . . . ?
N1 C1 C2 O2 82.3(4) . . . . ?
C11 N1 C1B C2B 171.9(4) . . . . ?
C10 N1 C1B C2B -75.2(5) . . . . ?
C3 N1 C1B C2B 59.6(5) . . . . ?
C1 N1 C1B C2B -38.0(4) . . . . ?
C2 O2 C2B C1B -38.1(4) . . . . ?
N1 C1B C2B O2 -92.1(5) . . . . ?
C11 N1 C3 C4 61.0(3) . . . . ?
C10 N1 C3 C4 -59.0(3) . . . . ?
C1 N1 C3 C4 -165.7(3) . . . . ?
C1B N1 C3 C4 159.1(3) . . . . ?
N1 C3 C4 C5 89.9(3) . . . . ?
N1 C3 C4 C9 -93.7(3) . . . . ?
C9 C4 C5 F5 -178.1(2) . . . . ?
C3 C4 C5 F5 -1.6(3) . . . . ?
C9 C4 C5 C6 2.2(3) . . . . ?
C3 C4 C5 C6 178.8(2) . . . . ?
F5 C5 C6 F6 -1.0(3) . . . . ?
C4 C5 C6 F6 178.6(2) . . . . ?
F5 C5 C6 C7 179.4(2) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
F6 C6 C7 F7 -0.3(3) . . . . ?
C5 C6 C7 F7 179.32(19) . . . . ?
F6 C6 C7 C8 179.5(2) . . . . ?
C5 C6 C7 C8 -0.9(3) . . . . ?
F7 C7 C8 F8 0.2(3) . . . . ?
C6 C7 C8 F8 -179.6(2) . . . . ?
F7 C7 C8 C9 -178.8(2) . . . . ?
C6 C7 C8 C9 1.4(3) . . . . ?
F8 C8 C9 F9 0.8(3) . . . . ?
C7 C8 C9 F9 179.8(2) . . . . ?
F8 C8 C9 C4 -179.1(2) . . . . ?
C7 C8 C9 C4 -0.1(3) . . . . ?
C5 C4 C9 F9 178.4(2) . . . . ?
C3 C4 C9 F9 1.8(3) . . . . ?
C5 C4 C9 C8 -1.7(3) . . . . ?
C3 C4 C9 C8 -178.3(2) . . . . ?
C10A N1A C1A C2A -168.39(19) . . . . ?
C11A N1A C1A C2A -50.9(3) . . . . ?
C3A N1A C1A C2A 70.5(2) . . . . ?
N1A C1A C2A O2A -171.13(19) . . . . ?
C10A N1A C3A C4A -57.3(2) . . . . ?
C11A N1A C3A C4A -173.93(18) . . . . ?
C1A N1A C3A C4A 62.9(2) . . . . ?
N1A C3A C4A C9A -93.0(3) . . . . ?
N1A C3A C4A C5A 92.2(3) . . . . ?
C9A C4A C5A F5A -178.7(2) . . . . ?
C3A C4A C5A F5A -3.6(3) . . . . ?
C9A C4A C5A C6A 0.7(3) . . . . ?
C3A C4A C5A C6A 175.8(2) . . . . ?
F5A C5A C6A F6A -1.9(3) . . . . ?
C4A C5A C6A F6A 178.7(2) . . . . ?
F5A C5A C6A C7A 178.9(2) . . . . ?
C4A C5A C6A C7A -0.5(4) . . . . ?
F6A C6A C7A F7A -1.0(4) . . . . ?
C5A C6A C7A F7A 178.2(2) . . . . ?
F6A C6A C7A C8A -179.4(2) . . . . ?
C5A C6A C7A C8A -0.1(4) . . . . ?
F7A C7A C8A F8A -0.2(4) . . . . ?
C6A C7A C8A F8A 178.2(2) . . . . ?
F7A C7A C8A C9A -177.8(2) . . . . ?
C6A C7A C8A C9A 0.6(4) . . . . ?
F8A C8A C9A F9A -0.7(4) . . . . ?
C7A C8A C9A F9A 177.0(2) . . . . ?
F8A C8A C9A C4A -178.0(2) . . . . ?
C7A C8A C9A C4A -0.3(4) . . . . ?
C5A C4A C9A F9A -177.6(2) . . . . ?
C3A C4A C9A F9A 7.4(3) . . . . ?
C5A C4A C9A C8A -0.3(4) . . . . ?
C3A C4A C9A C8A -175.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 Br2 0.817(17) 2.497(18) 3.3058(16) 171(3) 1_655
O2A H2AO Br1 0.820(18) 2.43(2) 3.2279(16) 163(3) .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.061

_iucr_refine_instructions_details 
;
TITL mm-tb-1-1 in P 21/n
CELL   0.71073   6.8660  14.2952  26.3661  90.000  94.417  90.000
ZERR     8       0.0001   0.0003   0.0005   0.000   0.001   0.000
LATT  1
SYMM 1/2-X,1/2+Y,1/2-Z
SFAC        C       H       N       O       F       BR
UNIT        88     104       8       8      40       8
L.S.      10
OMIT -3 50.5
OMIT 0 1 1
TEMP  -150
SIZE  0.38 0.30 0.24
EQIV $1 x+1, y, z
HTAB O2 Br2_$1
HTAB O2A Br1
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.019900    2.375600
FVAR       0.28264
BR1   6    0.743429    0.166732    0.458304    11.00000    0.02020    0.02162 =
         0.02182   -0.00252   -0.00221   -0.00122
BR2   6    0.486390    0.376145    0.223537    11.00000    0.02609    0.03116 =
         0.02244   -0.00504   -0.00411    0.00631
MOLE 1
F5    5    0.815063    0.190875   -0.012135    11.00000    0.02621    0.03147 =
         0.05828    0.00843    0.00516   -0.00067
F6    5    0.552294    0.081965   -0.063632    11.00000    0.04869    0.02832 =
         0.02360   -0.00200    0.00764    0.00406
F7    5    0.204143    0.044012   -0.025035    11.00000    0.03615    0.02773 =
         0.03290   -0.00480   -0.00856   -0.00790
F8    5    0.125154    0.115342    0.066302    11.00000    0.03483    0.03956 =
         0.03410    0.00743    0.00962    0.00247
F9    5    0.386448    0.226221    0.117928    11.00000    0.07149    0.03483 =
         0.02017   -0.00715   -0.00019    0.01128
O2    4    1.062640    0.328305    0.160792    11.00000    0.02852    0.02829 =
         0.03358    0.00765   -0.01307   -0.00230
H2    2    1.171912    0.333786    0.175128    11.00000   -1.50000
DFIX 0.84 O2 H2
N1    3    0.741945    0.379276    0.070605    11.00000    0.04053    0.01563 =
         0.04000    0.00188   -0.02442    0.00012
PART 1
C1    1    0.933172    0.429558    0.092938    10.60000    0.02223    0.01893 =
         0.02818    0.00284   -0.00504   -0.00628
AFIX  23
H1A   2    1.045979    0.404589    0.075997    10.60000   -1.20000
H1B   2    0.922913    0.497246    0.085253    10.60000   -1.20000
AFIX   0
C2    1    0.969920    0.416656    0.149652    10.60000    0.02854    0.02357 =
         0.02554   -0.00309   -0.00848   -0.00259
AFIX  23
H2A   2    1.054408    0.467843    0.163935    10.60000   -1.20000
H2B   2    0.844432    0.419458    0.165737    10.60000   -1.20000
AFIX   0
PART 2
C1B   1    0.845725    0.435641    0.116754    10.40000    0.02194    0.02266 =
         0.02227   -0.00188    0.00022   -0.00650
AFIX  23
H1B1  2    0.839571    0.503599    0.109578    10.40000   -1.20000
H1B2  2    0.779050    0.423521    0.148082    10.40000   -1.20000
AFIX   0
C2B   1    1.055839    0.404178    0.123903    10.40000    0.02713    0.02532 =
         0.02370    0.00563   -0.00244   -0.00385
AFIX  23
H2B1  2    1.101278    0.382145    0.091229    10.40000   -1.20000
H2B2  2    1.140570    0.456480    0.136639    10.40000   -1.20000
AFIX   0
PART 0
C3    1    0.756447    0.275492    0.083773    11.00000    0.05288    0.01468 =
         0.05212    0.00483   -0.03327   -0.00330
AFIX  23
H3A   2    0.888878    0.253140    0.077442    11.00000   -1.20000
H3B   2    0.740359    0.267826    0.120533    11.00000   -1.20000
AFIX   0
C4    1    0.607786    0.214766    0.054175    11.00000    0.03224    0.01641 =
         0.03023    0.00328   -0.01389    0.00118
C5    1    0.644442    0.174600    0.008202    11.00000    0.02410    0.01797 =
         0.03356    0.00643   -0.00177    0.00346
C6    1    0.511290    0.117865   -0.018503    11.00000    0.03249    0.01669 =
         0.02049   -0.00005    0.00083    0.00463
C7    1    0.335555    0.098242    0.000758    11.00000    0.02773    0.01474 =
         0.02155    0.00005   -0.00637   -0.00138
C8    1    0.295763    0.134687    0.047115    11.00000    0.02536    0.01981 =
         0.02403    0.00460    0.00084    0.00314
C9    1    0.431034    0.191885    0.072871    11.00000    0.04420    0.01837 =
         0.01699   -0.00091   -0.00568    0.00791
C10   1    0.767176    0.395930    0.015654    11.00000    0.02842    0.02352 =
         0.05304    0.00492    0.01200    0.00160
AFIX  33
H10A  2    0.894375    0.371701    0.007329    11.00000   -1.50000
H10B  2    0.760613    0.463220    0.008623    11.00000   -1.50000
H10C  2    0.663118    0.363812   -0.005098    11.00000   -1.50000
AFIX   0
C11   1    0.548555    0.417577    0.081709    11.00000    0.07445    0.02175 =
         0.02466   -0.00044    0.01415    0.00482
AFIX  33
H11A  2    0.528503    0.407908    0.117734    11.00000   -1.50000
H11B  2    0.445402    0.385418    0.060661    11.00000   -1.50000
H11C  2    0.544231    0.484664    0.074054    11.00000   -1.50000
AFIX   0
MOLE 2
F5A   5   -0.307136    0.156945    0.187802    11.00000    0.03909    0.03347 =
         0.02783   -0.00338   -0.01429    0.01149
F6A   5   -0.251890    0.011551    0.126914    11.00000    0.07355    0.04165 =
         0.02637   -0.01203   -0.01415    0.00106
F7A   5    0.099631   -0.077059    0.131198    11.00000    0.08283    0.03062 =
         0.04132   -0.01429    0.02344    0.00333
F8A   5    0.394909   -0.017292    0.198565    11.00000    0.03809    0.04678 =
         0.08732   -0.01697    0.02592    0.01067
F9A   5    0.336616    0.124993    0.261326    11.00000    0.01756    0.04458 =
         0.06448   -0.01652    0.00410   -0.00237
O2A   4    0.344025    0.125720    0.389139    11.00000    0.03258    0.03119 =
         0.04523   -0.00582   -0.02228    0.00974
H2AO  2    0.440934    0.148169    0.404720    11.00000   -1.50000
DFIX 0.84 O2A H2AO
N1A   3   -0.090731    0.210294    0.310778    11.00000    0.01661    0.01810 =
         0.01825    0.00041   -0.00031    0.00026
C1A   1    0.045819    0.150933    0.344882    11.00000    0.02089    0.01803 =
         0.02033    0.00119   -0.00363    0.00289
AFIX  23
H1A1  2    0.082531    0.095121    0.325535    11.00000   -1.20000
H1A2  2   -0.025522    0.128833    0.373835    11.00000   -1.20000
AFIX   0
C2A   1    0.231537    0.199706    0.365834    11.00000    0.02374    0.02649 =
         0.03033   -0.00553   -0.01013    0.00337
AFIX  23
H2A1  2    0.300055    0.229077    0.338229    11.00000   -1.20000
H2A2  2    0.202855    0.248172    0.391025    11.00000   -1.20000
AFIX   0
C3A   1   -0.013939    0.231813    0.259143    11.00000    0.02237    0.01813 =
         0.02013    0.00129    0.00389   -0.00166
AFIX  23
H3A1  2   -0.106328    0.274902    0.240300    11.00000   -1.20000
H3A2  2    0.112825    0.264645    0.264809    11.00000   -1.20000
AFIX   0
C4A   1    0.013568    0.147079    0.226790    11.00000    0.02507    0.01737 =
         0.01980    0.00291    0.00628   -0.00190
C5A   1   -0.132134    0.114703    0.191521    11.00000    0.03417    0.02156 =
         0.01697    0.00375    0.00200    0.00289
C6A   1   -0.104581    0.041003    0.159556    11.00000    0.05109    0.02355 =
         0.01789    0.00001   -0.00016   -0.00176
C7A   1    0.072781   -0.003266    0.161395    11.00000    0.05730    0.01822 =
         0.02548   -0.00335    0.01911   -0.00129
C8A   1    0.222369    0.026778    0.195308    11.00000    0.03355    0.02587 =
         0.04614   -0.00096    0.02179    0.00302
C9A   1    0.190273    0.100386    0.227107    11.00000    0.02363    0.02538 =
         0.03334   -0.00209    0.00945   -0.00585
C10A  1   -0.280866    0.158898    0.302692    11.00000    0.01522    0.03282 =
         0.02416    0.00151    0.00072   -0.00418
AFIX  33
H10D  2   -0.259155    0.098602    0.286364    11.00000   -1.50000
H10E  2   -0.373091    0.196173    0.280849    11.00000   -1.50000
H10F  2   -0.334666    0.148316    0.335576    11.00000   -1.50000
AFIX   0
C11A  1   -0.130784    0.302097    0.335826    11.00000    0.02968    0.02081 =
         0.02310   -0.00313   -0.00079    0.00617
AFIX  33
H11D  2   -0.008650    0.337336    0.341584    11.00000   -1.50000
H11E  2   -0.185647    0.290469    0.368473    11.00000   -1.50000
H11F  2   -0.224152    0.338305    0.313743    11.00000   -1.50000
HKLF   4
 
REM  mm-tb-1-1 in P 21/n
REM R1 =  0.0245 for   4085 Fo > 4sig(Fo)  and  0.0311 for all   4666 data
REM    367 parameters refined using      2 restraints
 
END
 
WGHT      0.0199      2.3783
REM Highest difference peak  0.238,  deepest hole -0.341,  1-sigma level  0.061
Q1    1   0.1373  0.0066  0.1850  11.00000  0.05    0.24
Q2    1   0.0804  0.1107  0.2342  11.00000  0.05    0.23
Q3    1   0.2311  0.0773  0.1958  11.00000  0.05    0.23
Q4    1  -0.0238  0.0081  0.1708  11.00000  0.05    0.22
Q5    1  -0.4940  0.1307  0.1920  11.00000  0.05    0.22
Q6    1   0.7745  0.2737  0.0700  11.00000  0.05    0.22
Q7    1   0.9070  0.3758  0.0364  11.00000  0.05    0.22
Q8    1   0.6000  0.1289  0.0007  11.00000  0.05    0.22
Q9    1  -0.1693  0.1834  0.3066  11.00000  0.05    0.21
Q10   1   0.5162  0.3161  0.2695  11.00000  0.05    0.21
Q11   1   0.4072  0.1188 -0.0124  11.00000  0.05    0.21
Q12   1  -0.1349  0.0623  0.1814  11.00000  0.05    0.21
Q13   1   0.6619  0.2756  0.1351  11.00000  0.05    0.21
Q14   1   0.3317  0.1875  0.0541  11.00000  0.05    0.21
Q15   1   0.1329  0.1808  0.3569  11.00000  0.05    0.21
Q16   1   0.5400  0.1872  0.0693  11.00000  0.05    0.20
Q17   1   0.8573  0.4864  0.0966  11.00000  0.05    0.20
Q18   1   0.3227  0.1305  0.0204  11.00000  0.05    0.20
Q19   1  -0.3853  0.1756  0.3346  11.00000  0.05    0.20
Q20   1   0.5599  0.1554 -0.0082  11.00000  0.05    0.20
Q21   1  -0.1002  0.0984  0.1611  11.00000  0.05    0.20
Q22   1   0.4270  0.2493  0.1162  11.00000  0.05    0.20
Q23   1   0.6062  0.4784  0.0827  11.00000  0.05    0.20
Q24   1  -0.0414  0.2159  0.2876  11.00000  0.05    0.20
Q25   1   0.6691  0.2440  0.0636  11.00000  0.05    0.20
;
_database_code_depnum_ccdc_archive 'CCDC 1005279'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-117-br

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'4(C12 H13 F5 N S), 0.4(C2 H6 O), 3(C H Cl3), 4(Br), 2.4(O)'
_chemical_formula_sum            'C51.80 H57.40 Br4 Cl9 F20 N4 O2.80 S4'
_chemical_formula_weight         1927.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.8941(5)
_cell_length_b                   10.1069(3)
_cell_length_c                   10.1222(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.532(2)
_cell_angle_gamma                90.00
_cell_volume                     1793.68(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4551
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             956
_exptl_absorpt_coefficient_mu    2.791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4881
_exptl_absorpt_correction_T_max  0.9209
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18769
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3138
_reflns_number_gt                2547
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2006)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0125P)^2^+4.1232P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3138
_refine_ls_number_parameters     244
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0757
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.37780(2) -0.03623(3) 0.18322(3) 0.02386(12) Uani 1 1 d . . .
S1 S 0.40597(6) 0.32617(9) 0.09213(9) 0.0308(2) Uani 1 1 d . . .
F7 F 0.20055(11) 0.4806(2) 0.4247(2) 0.0315(5) Uani 1 1 d . . .
F8 F 0.04973(12) 0.4525(2) 0.3317(2) 0.0468(6) Uani 1 1 d . . .
F9 F -0.01890(12) 0.5801(3) 0.1018(2) 0.0489(7) Uani 1 1 d . . .
F10 F 0.06531(12) 0.7254(3) -0.0380(2) 0.0460(6) Uani 1 1 d . . .
F11 F 0.21564(12) 0.7544(2) 0.0543(2) 0.0346(5) Uani 1 1 d . . .
N1 N 0.35767(15) 0.5662(3) 0.2672(3) 0.0178(6) Uani 1 1 d . . .
C1 C 0.3475(2) 0.4231(3) 0.3054(4) 0.0223(8) Uani 1 1 d . . .
H1A H 0.3492 0.4182 0.4037 0.027 Uiso 1 1 calc R . .
H1B H 0.2965 0.3923 0.2588 0.027 Uiso 1 1 calc R . .
C2 C 0.4075(2) 0.3308(3) 0.2704(3) 0.0236(8) Uani 1 1 d . . .
H2A H 0.3988 0.2404 0.3019 0.028 Uiso 1 1 calc R . .
H2B H 0.4585 0.3601 0.3184 0.028 Uiso 1 1 calc R . .
C3 C 0.4158(2) 0.5028(4) 0.0684(4) 0.0277(9) Uani 1 1 d . . .
H3A H 0.4667 0.5319 0.1175 0.033 Uiso 1 1 calc R . .
H3B H 0.4126 0.5213 -0.0286 0.033 Uiso 1 1 calc R . .
C4 C 0.3550(2) 0.5807(3) 0.1181(3) 0.0228(8) Uani 1 1 d . . .
H4A H 0.3606 0.6755 0.0974 0.027 Uiso 1 1 calc R . .
H4B H 0.3043 0.5514 0.0684 0.027 Uiso 1 1 calc R . .
C5 C 0.29482(18) 0.6499(3) 0.3069(3) 0.0210(8) Uani 1 1 d . . .
H5A H 0.2998 0.6436 0.4059 0.025 Uiso 1 1 calc R . .
H5B H 0.3040 0.7434 0.2856 0.025 Uiso 1 1 calc R . .
C6 C 0.21369(19) 0.6162(3) 0.2423(3) 0.0211(8) Uani 1 1 d . . .
C7 C 0.1684(2) 0.5408(3) 0.3088(4) 0.0249(8) Uani 1 1 d . . .
C8 C 0.0910(2) 0.5263(4) 0.2631(4) 0.0322(9) Uani 1 1 d . . .
C9 C 0.0565(2) 0.5899(4) 0.1461(4) 0.0331(9) Uani 1 1 d . . .
C10 C 0.0995(2) 0.6640(4) 0.0759(4) 0.0326(9) Uani 1 1 d . . .
C11 C 0.1769(2) 0.6761(3) 0.1238(4) 0.0258(8) Uani 1 1 d . . .
C12 C 0.4314(2) 0.6214(4) 0.3470(3) 0.0250(8) Uani 1 1 d . . .
H12A H 0.4324 0.6109 0.4436 0.037 Uiso 1 1 calc R . .
H12B H 0.4352 0.7155 0.3260 0.037 Uiso 1 1 calc R . .
H12C H 0.4746 0.5736 0.3233 0.037 Uiso 1 1 calc R . .
C13 C 0.1912(3) 0.0995(6) 0.2234(6) 0.0312(13) Uani 0.75 1 d P A 1
H13 H 0.2317 0.0793 0.1711 0.037 Uiso 0.75 1 calc PR A 1
Cl1 Cl 0.23382(10) 0.15732(14) 0.37793(15) 0.0450(4) Uani 0.75 1 d P A 1
Cl2 Cl 0.14252(11) -0.05045(17) 0.2463(2) 0.0648(6) Uani 0.75 1 d P A 1
Cl3 Cl 0.12962(14) 0.2135(2) 0.13490(18) 0.0733(6) Uani 0.75 1 d P A 1
O14 O 0.1137(9) 0.0025(16) 0.1678(16) 0.019(4) Uiso 0.15 1 d P B 2
O14A O 0.2361(13) -0.043(2) 0.329(2) 0.052(5) Uiso 0.15 1 d P C 3
O14B O 0.2015(13) 0.160(2) 0.434(2) 0.050(6) Uiso 0.15 1 d P D 4
O14C O 0.1638(11) 0.2513(19) 0.096(2) 0.031(5) Uiso 0.15 1 d P E 5
O15 O 0.1836(18) -0.036(3) 0.328(3) 0.032(6) Uiso 0.10 1 d PD F 6
H15 H 0.1970 0.0029 0.4021 0.048 Uiso 0.10 1 calc PR F 6
C16 C 0.171(3) 0.051(3) 0.229(4) 0.023(7) Uiso 0.10 1 d PD F 6
H16A H 0.1156 0.0386 0.1924 0.027 Uiso 0.10 1 calc PR F 6
H16B H 0.1966 0.0103 0.1615 0.027 Uiso 0.10 1 calc PR F 6
C17 C 0.180(2) 0.192(3) 0.205(4) 0.023(7) Uiso 0.10 1 d PD F 6
H17A H 0.1547 0.2141 0.1129 0.034 Uiso 0.10 1 calc PR F 6
H17B H 0.2348 0.2124 0.2170 0.034 Uiso 0.10 1 calc PR F 6
H17C H 0.1580 0.2438 0.2692 0.034 Uiso 0.10 1 calc PR F 6

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0280(2) 0.02174(18) 0.02187(19) -0.00052(16) 0.00513(14) -0.00198(16)
S1 0.0380(6) 0.0297(5) 0.0235(5) -0.0069(4) 0.0038(4) 0.0102(4)
F7 0.0319(12) 0.0365(12) 0.0273(11) 0.0097(10) 0.0086(9) -0.0034(10)
F8 0.0308(13) 0.0578(16) 0.0545(15) 0.0106(13) 0.0148(11) -0.0163(12)
F9 0.0203(12) 0.0718(18) 0.0533(16) 0.0035(13) 0.0041(11) -0.0050(12)
F10 0.0287(13) 0.0622(16) 0.0445(15) 0.0162(13) 0.0008(11) 0.0077(12)
F11 0.0286(12) 0.0373(12) 0.0389(13) 0.0159(10) 0.0092(10) 0.0035(10)
N1 0.0213(15) 0.0160(14) 0.0163(14) 0.0011(11) 0.0044(12) -0.0002(12)
C1 0.0244(19) 0.0213(18) 0.0206(18) 0.0003(15) 0.0027(15) -0.0021(15)
C2 0.027(2) 0.0213(18) 0.0219(19) -0.0005(15) 0.0028(15) 0.0027(15)
C3 0.028(2) 0.035(2) 0.0203(18) 0.0013(16) 0.0070(15) 0.0042(17)
C4 0.0255(19) 0.0248(18) 0.0183(18) 0.0034(15) 0.0052(15) 0.0029(15)
C5 0.0207(19) 0.0187(17) 0.0249(19) -0.0012(15) 0.0078(15) 0.0006(14)
C6 0.0213(19) 0.0172(17) 0.0253(19) -0.0023(15) 0.0054(15) 0.0026(15)
C7 0.026(2) 0.0223(18) 0.027(2) -0.0001(17) 0.0071(15) -0.0022(16)
C8 0.025(2) 0.034(2) 0.040(2) -0.0027(19) 0.0120(17) -0.0087(18)
C9 0.020(2) 0.042(2) 0.037(2) -0.0028(19) 0.0031(17) -0.0023(18)
C10 0.026(2) 0.035(2) 0.036(2) 0.0062(19) 0.0042(17) 0.0046(18)
C11 0.024(2) 0.0232(18) 0.033(2) 0.0034(17) 0.0124(16) -0.0026(16)
C12 0.026(2) 0.0243(19) 0.025(2) -0.0023(16) 0.0047(16) -0.0029(16)
C13 0.023(3) 0.029(3) 0.041(3) -0.005(3) 0.005(2) -0.004(2)
Cl1 0.0600(10) 0.0394(8) 0.0333(8) -0.0028(6) 0.0035(7) -0.0075(7)
Cl2 0.0579(11) 0.0423(9) 0.1066(17) -0.0324(10) 0.0460(12) -0.0189(9)
Cl3 0.0915(16) 0.0792(14) 0.0421(10) -0.0080(10) -0.0039(11) 0.0523(13)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.800(3) . ?
S1 C3 1.814(4) . ?
F7 C7 1.345(4) . ?
F8 C8 1.338(4) . ?
F9 C9 1.337(4) . ?
F10 C10 1.345(4) . ?
F11 C11 1.341(4) . ?
N1 C4 1.507(4) . ?
N1 C12 1.510(4) . ?
N1 C1 1.518(4) . ?
N1 C5 1.524(4) . ?
C1 C2 1.516(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.510(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.507(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.381(5) . ?
C6 C11 1.387(5) . ?
C7 C8 1.379(5) . ?
C8 C9 1.380(5) . ?
C9 C10 1.370(5) . ?
C10 C11 1.377(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 Cl1 1.701(5) . ?
C13 Cl3 1.717(6) . ?
C13 Cl2 1.787(6) . ?
C13 H13 1.0000 . ?
O15 C16 1.324(19) . ?
O15 H15 0.8400 . ?
C16 C17 1.457(19) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C3 97.17(16) . . ?
C4 N1 C12 110.5(3) . . ?
C4 N1 C1 111.5(2) . . ?
C12 N1 C1 110.6(2) . . ?
C4 N1 C5 109.4(2) . . ?
C12 N1 C5 105.4(2) . . ?
C1 N1 C5 109.2(2) . . ?
C2 C1 N1 113.6(3) . . ?
C2 C1 H1A 108.8 . . ?
N1 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
N1 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C1 C2 S1 112.4(2) . . ?
C1 C2 H2A 109.1 . . ?
S1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
S1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 S1 111.9(3) . . ?
C4 C3 H3A 109.2 . . ?
S1 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
S1 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
N1 C4 C3 113.7(3) . . ?
N1 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
N1 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 N1 117.2(3) . . ?
C6 C5 H5A 108.0 . . ?
N1 C5 H5A 108.0 . . ?
C6 C5 H5B 108.0 . . ?
N1 C5 H5B 108.0 . . ?
H5A C5 H5B 107.2 . . ?
C7 C6 C11 116.0(3) . . ?
C7 C6 C5 121.4(3) . . ?
C11 C6 C5 121.8(3) . . ?
F7 C7 C8 118.1(3) . . ?
F7 C7 C6 119.0(3) . . ?
C8 C7 C6 122.9(3) . . ?
F8 C8 C7 120.5(3) . . ?
F8 C8 C9 120.5(3) . . ?
C7 C8 C9 119.0(3) . . ?
F9 C9 C10 120.1(3) . . ?
F9 C9 C8 120.1(3) . . ?
C10 C9 C8 119.9(3) . . ?
F10 C10 C9 119.4(3) . . ?
F10 C10 C11 120.9(3) . . ?
C9 C10 C11 119.7(3) . . ?
F11 C11 C10 117.2(3) . . ?
F11 C11 C6 120.3(3) . . ?
C10 C11 C6 122.4(3) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Cl1 C13 Cl3 111.9(3) . . ?
Cl1 C13 Cl2 108.2(3) . . ?
Cl3 C13 Cl2 111.0(3) . . ?
Cl1 C13 H13 108.6 . . ?
Cl3 C13 H13 108.6 . . ?
Cl2 C13 H13 108.6 . . ?
C16 O15 H15 109.5 . . ?
O15 C16 C17 140(4) . . ?
O15 C16 H16A 101.9 . . ?
C17 C16 H16A 101.9 . . ?
O15 C16 H16B 101.9 . . ?
C17 C16 H16B 101.9 . . ?
H16A C16 H16B 104.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 59.0(4) . . . . ?
C12 N1 C1 C2 -64.3(3) . . . . ?
C5 N1 C1 C2 -179.9(3) . . . . ?
N1 C1 C2 S1 -61.4(3) . . . . ?
C3 S1 C2 C1 54.7(3) . . . . ?
C2 S1 C3 C4 -55.1(3) . . . . ?
C12 N1 C4 C3 63.6(4) . . . . ?
C1 N1 C4 C3 -59.8(4) . . . . ?
C5 N1 C4 C3 179.2(3) . . . . ?
S1 C3 C4 N1 62.4(3) . . . . ?
C4 N1 C5 C6 61.6(4) . . . . ?
C12 N1 C5 C6 -179.7(3) . . . . ?
C1 N1 C5 C6 -60.8(4) . . . . ?
N1 C5 C6 C7 99.0(4) . . . . ?
N1 C5 C6 C11 -91.6(4) . . . . ?
C11 C6 C7 F7 -179.7(3) . . . . ?
C5 C6 C7 F7 -9.7(5) . . . . ?
C11 C6 C7 C8 -1.1(5) . . . . ?
C5 C6 C7 C8 168.9(3) . . . . ?
F7 C7 C8 F8 -1.1(5) . . . . ?
C6 C7 C8 F8 -179.7(3) . . . . ?
F7 C7 C8 C9 178.4(3) . . . . ?
C6 C7 C8 C9 -0.2(6) . . . . ?
F8 C8 C9 F9 1.3(6) . . . . ?
C7 C8 C9 F9 -178.2(3) . . . . ?
F8 C8 C9 C10 -179.2(4) . . . . ?
C7 C8 C9 C10 1.3(6) . . . . ?
F9 C9 C10 F10 -0.6(6) . . . . ?
C8 C9 C10 F10 180.0(4) . . . . ?
F9 C9 C10 C11 178.5(3) . . . . ?
C8 C9 C10 C11 -1.0(6) . . . . ?
F10 C10 C11 F11 1.9(5) . . . . ?
C9 C10 C11 F11 -177.1(3) . . . . ?
F10 C10 C11 C6 178.7(3) . . . . ?
C9 C10 C11 C6 -0.3(6) . . . . ?
C7 C6 C11 F11 178.0(3) . . . . ?
C5 C6 C11 F11 8.1(5) . . . . ?
C7 C6 C11 C10 1.3(5) . . . . ?
C5 C6 C11 C10 -168.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.080

_iucr_refine_instructions_details 
;
TITL mm-117-br in P 21/c
REM  transformed from space group : P21/a
CELL   0.71073 17.8941 10.1069 10.1222   90.000  101.532   90.000
ZERR   1        0.0005  0.0003  0.0003    0.000    0.002    0.000
LATT    1
SYMM   -X,1/2+Y,1/2-Z
SFAC        C       H       N       O        F       S       CL      BR
UNIT        51.80   57.40   4       2.80     20      4       9       4
L.S.      10
OMIT -3 50.05
OMIT 2 0 0
OMIT 1 1 0
OMIT 1 1 1
TEMP  -150
SIZE  0.30 0.20 0.03
DFIX 1.5 C16 C17
DFIX 1.4 C16 O15
EADP C17 C16
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.012500    4.123199
FVAR       0.41460
BR1   8    0.377796   -0.036234    0.183217    11.00000    0.02802    0.02174 =
         0.02187   -0.00052    0.00513   -0.00198
S1    6    0.405973    0.326167    0.092127    11.00000    0.03805    0.02970 =
         0.02354   -0.00689    0.00380    0.01016
F7    5    0.200546    0.480571    0.424725    11.00000    0.03189    0.03653 =
         0.02728    0.00971    0.00858   -0.00336
F8    5    0.049730    0.452466    0.331743    11.00000    0.03076    0.05779 =
         0.05450    0.01056    0.01481   -0.01629
F9    5   -0.018898    0.580124    0.101835    11.00000    0.02033    0.07179 =
         0.05332    0.00347    0.00410   -0.00505
F10   5    0.065313    0.725432   -0.038044    11.00000    0.02866    0.06220 =
         0.04454    0.01616    0.00081    0.00766
F11   5    0.215641    0.754442    0.054252    11.00000    0.02862    0.03728 =
         0.03889    0.01587    0.00919    0.00353
N1    3    0.357665    0.566171    0.267151    11.00000    0.02132    0.01604 =
         0.01627    0.00114    0.00438   -0.00019
C1    1    0.347524    0.423073    0.305444    11.00000    0.02436    0.02127 =
         0.02060    0.00034    0.00267   -0.00214
AFIX  23
H1A   2    0.349234    0.418161    0.403685    11.00000   -1.20000
H1B   2    0.296527    0.392332    0.258769    11.00000   -1.20000
AFIX   0
C2    1    0.407481    0.330795    0.270374    11.00000    0.02684    0.02128 =
         0.02189   -0.00055    0.00279    0.00266
AFIX  23
H2A   2    0.398771    0.240436    0.301911    11.00000   -1.20000
H2B   2    0.458509    0.360069    0.318397    11.00000   -1.20000
AFIX   0
C3    1    0.415834    0.502792    0.068406    11.00000    0.02848    0.03529 =
         0.02033    0.00131    0.00703    0.00415
AFIX  23
H3A   2    0.466664    0.531858    0.117541    11.00000   -1.20000
H3B   2    0.412618    0.521308   -0.028610    11.00000   -1.20000
AFIX   0
C4    1    0.354953    0.580736    0.118139    11.00000    0.02554    0.02478 =
         0.01830    0.00341    0.00523    0.00293
AFIX  23
H4A   2    0.360622    0.675495    0.097399    11.00000   -1.20000
H4B   2    0.304301    0.551430    0.068422    11.00000   -1.20000
AFIX   0
C5    1    0.294817    0.649922    0.306872    11.00000    0.02069    0.01867 =
         0.02492   -0.00117    0.00783    0.00064
AFIX  23
H5A   2    0.299824    0.643611    0.405857    11.00000   -1.20000
H5B   2    0.304018    0.743389    0.285586    11.00000   -1.20000
AFIX   0
C6    1    0.213694    0.616230    0.242290    11.00000    0.02130    0.01719 =
         0.02525   -0.00226    0.00543    0.00260
C7    1    0.168445    0.540765    0.308762    11.00000    0.02624    0.02232 =
         0.02701   -0.00007    0.00713   -0.00224
C8    1    0.090976    0.526295    0.263069    11.00000    0.02535    0.03376 =
         0.03970   -0.00273    0.01205   -0.00866
C9    1    0.056495    0.589904    0.146054    11.00000    0.01959    0.04169 =
         0.03688   -0.00275    0.00307   -0.00226
C10   1    0.099536    0.663958    0.075872    11.00000    0.02604    0.03492 =
         0.03588    0.00624    0.00419    0.00457
C11   1    0.176859    0.676094    0.123762    11.00000    0.02425    0.02324 =
         0.03264    0.00338    0.01235   -0.00258
C12   1    0.431442    0.621372    0.347046    11.00000    0.02555    0.02425 =
         0.02495   -0.00227    0.00469   -0.00291
AFIX  33
H12A  2    0.432408    0.610875    0.443621    11.00000   -1.50000
H12B  2    0.435231    0.715488    0.326038    11.00000   -1.50000
H12C  2    0.474557    0.573569    0.323318    11.00000   -1.50000
AFIX   0
PART 1
C13   1    0.191212    0.099535    0.223389    10.75000    0.02300    0.02926 =
         0.04059   -0.00490    0.00462   -0.00390
AFIX  13
H13   2    0.231680    0.079253    0.171083    10.75000   -1.20000
AFIX   0
CL1   7    0.233818    0.157318    0.377933    10.75000    0.06001    0.03940 =
         0.03329   -0.00282    0.00348   -0.00753
CL2   7    0.142521   -0.050448    0.246326    10.75000    0.05787    0.04233 =
         0.10659   -0.03243    0.04604   -0.01887
CL3   7    0.129624    0.213476    0.134896    10.75000    0.09146    0.07916 =
         0.04208   -0.00802   -0.00392    0.05227
PART 2
O14   4    0.113743    0.002451    0.167769    10.15000    0.01883
PART 3
O14A  4    0.236089   -0.042697    0.328715    10.15000    0.05209
PART 4
O14B  4    0.201541    0.160278    0.434149    10.15000    0.04988
PART 5
O14C  4    0.163781    0.251295    0.095825    10.15000    0.03125
PART 6
O15   4    0.183607   -0.036478    0.328021    10.10000    0.03167
AFIX 143
H15   2    0.196982    0.002862    0.402080    10.10000   -1.50000
AFIX   0
C16   1    0.170705    0.051355    0.229067    10.10000    0.02267
AFIX  23
H16A  2    0.115610    0.038596    0.192375    10.10000   -1.20000
H16B  2    0.196568    0.010299    0.161537    10.10000   -1.20000
AFIX   0
C17   1    0.180331    0.191939    0.205084    10.10000    0.02267
AFIX  33
H17A  2    0.154708    0.214128    0.112885    10.10000   -1.50000
H17B  2    0.234798    0.212438    0.217006    10.10000   -1.50000
H17C  2    0.157959    0.243781    0.269236    10.10000   -1.50000
HKLF   4
 
REM  mm-117-br in P 21/c
REM R1 =  0.0377 for   2547 Fo > 4sig(Fo)  and  0.0537 for all   3138 data
REM    244 parameters refined using      2 restraints
 
END
 
WGHT      0.0125      4.1272
REM Highest difference peak  0.526,  deepest hole -0.363,  1-sigma level  0.080
Q1    1   0.1739  0.0277  0.2820  11.00000  0.05    0.53
Q2    1   0.4438 -0.0265  0.2142  11.00000  0.05    0.42
Q3    1   0.1076  0.1249  0.1263  11.00000  0.05    0.39
Q4    1   0.1925  0.1010  0.3187  11.00000  0.05    0.38
Q5    1   0.2002  0.1709  0.2974  11.00000  0.05    0.37
Q6    1   0.3963  0.2500  0.2410  11.00000  0.05    0.37
Q7    1   0.1487  0.1367  0.2298  11.00000  0.05    0.36
Q8    1   0.0870  0.0593  0.1226  11.00000  0.05    0.34
Q9    1   0.2620  0.6070  0.2610  11.00000  0.05    0.32
Q10   1   0.2041  0.2240  0.3567  11.00000  0.05    0.32
Q11   1   0.3167 -0.0335  0.1760  11.00000  0.05    0.32
Q12   1   0.2275  0.3439  0.4160  11.00000  0.05    0.29
Q13   1   0.1880  0.1507  0.4930  11.00000  0.05    0.28
Q14   1   0.2070  0.0852  0.3758  11.00000  0.05    0.28
Q15   1   0.3532  0.3222  0.2781  11.00000  0.05    0.28
Q16   1   0.4459  0.3955  0.0879  11.00000  0.05    0.28
Q17   1   0.4614  0.3196  0.3109  11.00000  0.05    0.27
Q18   1   0.0884  0.7883  0.0153  11.00000  0.05    0.27
Q19   1   0.2284  0.4165  0.3268  11.00000  0.05    0.27
Q20   1   0.2655 -0.1094  0.1818  11.00000  0.05    0.27
Q21   1   0.0617  0.0966  0.2419  11.00000  0.05    0.27
Q22   1   0.2154  0.5442  0.2619  11.00000  0.05    0.26
Q23   1   0.2308  0.8002  0.1337  11.00000  0.05    0.26
Q24   1  -0.0149  0.5396  0.4094  11.00000  0.05    0.26
Q25   1   0.3234  0.0262  0.0808  11.00000  0.05    0.26
;
_database_code_depnum_ccdc_archive 'CCDC 1005280'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-208

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H18 F4 N, C3 H7 N O, Br'
_chemical_formula_sum            'C16 H25 Br F4 N2 O'
_chemical_formula_weight         417.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.6426(2)
_cell_length_b                   11.6845(3)
_cell_length_c                   10.7767(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.3460(10)
_cell_angle_gamma                90.00
_cell_volume                     918.59(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2358
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    2.281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5477
_exptl_absorpt_correction_T_max  0.8386
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11604
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3178
_reflns_number_gt                2933
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2006)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.2557P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.063(8)
_refine_ls_number_reflns         3178
_refine_ls_number_parameters     223
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0640
_refine_ls_wR_factor_gt          0.0620
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.33041(4) 0.60909(4) 0.23750(3) 0.02226(9) Uani 1 1 d . . .
F9 F 0.0731(3) 0.99416(16) 0.59266(18) 0.0291(5) Uani 1 1 d . . .
F10 F 0.1529(3) 0.88334(18) 0.40097(18) 0.0344(5) Uani 1 1 d . . .
F12 F 0.2397(3) 0.54267(18) 0.6459(2) 0.0304(6) Uani 1 1 d . . .
F13 F 0.1610(3) 0.65311(15) 0.83883(18) 0.0298(5) Uani 1 1 d . . .
N1 N 0.2014(4) 0.9463(2) 0.9360(2) 0.0161(6) Uani 1 1 d . . .
C1 C 0.3004(5) 1.0384(3) 0.8819(3) 0.0223(7) Uani 1 1 d . . .
H1A H 0.4114 1.0620 0.9516 0.027 Uiso 1 1 calc R . .
H1B H 0.3413 1.0043 0.8112 0.027 Uiso 1 1 calc R . .
C2 C 0.1883(5) 1.1435(3) 0.8301(4) 0.0273(9) Uani 1 1 d . . .
H2A H 0.0613 1.1212 0.7861 0.041 Uiso 1 1 calc R . .
H2B H 0.2395 1.1825 0.7682 0.041 Uiso 1 1 calc R . .
H2C H 0.1913 1.1953 0.9022 0.041 Uiso 1 1 calc R . .
C3 C 0.3433(5) 0.8568(3) 1.0061(3) 0.0229(8) Uani 1 1 d . . .
H3A H 0.2782 0.7902 1.0281 0.027 Uiso 1 1 calc R . .
H3B H 0.4104 0.8300 0.9459 0.027 Uiso 1 1 calc R . .
C4 C 0.4806(5) 0.9008(3) 1.1294(4) 0.0318(9) Uani 1 1 d . . .
H4A H 0.5664 0.8394 1.1692 0.048 Uiso 1 1 calc R . .
H4B H 0.4157 0.9261 1.1904 0.048 Uiso 1 1 calc R . .
H4C H 0.5486 0.9653 1.1082 0.048 Uiso 1 1 calc R . .
C5 C 0.1054(5) 0.9997(3) 1.0256(3) 0.0201(7) Uani 1 1 d . . .
H5A H 0.0091 1.0520 0.9742 0.024 Uiso 1 1 calc R . .
H5B H 0.1952 1.0463 1.0914 0.024 Uiso 1 1 calc R . .
C6 C 0.0182(5) 0.9145(3) 1.0952(3) 0.0259(8) Uani 1 1 d . . .
H6A H -0.0420 0.9558 1.1504 0.039 Uiso 1 1 calc R . .
H6B H 0.1129 0.8640 1.1492 0.039 Uiso 1 1 calc R . .
H6C H -0.0728 0.8688 1.0311 0.039 Uiso 1 1 calc R . .
C7 C 0.0551(4) 0.8867(3) 0.8274(3) 0.0172(7) Uani 1 1 d . . .
H7A H -0.0058 0.8288 0.8674 0.021 Uiso 1 1 calc R . .
H7B H -0.0386 0.9442 0.7847 0.021 Uiso 1 1 calc R . .
C8 C 0.1189(4) 0.8285(3) 0.7240(3) 0.0166(7) Uani 1 1 d . . .
C9 C 0.1179(4) 0.8821(3) 0.6097(3) 0.0207(7) Uani 1 1 d . . .
C10 C 0.1567(5) 0.8251(3) 0.5098(3) 0.0219(8) Uani 1 1 d . . .
C11 C 0.1991(4) 0.7105(3) 0.5182(3) 0.0226(8) Uani 1 1 d . . .
H11 H 0.2259 0.6712 0.4489 0.027 Uiso 1 1 calc R . .
C12 C 0.2012(6) 0.6553(3) 0.6304(4) 0.0206(9) Uani 1 1 d . . .
C13 C 0.1618(4) 0.7124(3) 0.7309(3) 0.0207(7) Uani 1 1 d . . .
O14 O 0.6253(4) 0.7217(2) 0.8265(2) 0.0345(6) Uani 1 1 d . . .
N16 N 0.6453(4) 0.7517(2) 0.6221(3) 0.0240(7) Uani 1 1 d . . .
C15 C 0.6186(5) 0.7850(3) 0.7330(4) 0.0249(8) Uani 1 1 d D . .
H15 H 0.596(5) 0.8600(18) 0.738(4) 0.030 Uiso 1 1 d D . .
C17 C 0.6798(5) 0.6319(3) 0.5980(4) 0.0349(11) Uani 1 1 d . . .
H17A H 0.6569 0.5839 0.6661 0.052 Uiso 1 1 calc R . .
H17B H 0.8075 0.6230 0.5986 0.052 Uiso 1 1 calc R . .
H17C H 0.5980 0.6086 0.5131 0.052 Uiso 1 1 calc R . .
C18 C 0.6299(6) 0.8314(3) 0.5156(4) 0.0354(10) Uani 1 1 d . . .
H18A H 0.6134 0.9092 0.5442 0.053 Uiso 1 1 calc R . .
H18B H 0.5242 0.8105 0.4419 0.053 Uiso 1 1 calc R . .
H18C H 0.7417 0.8281 0.4890 0.053 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02159(14) 0.02348(16) 0.02334(15) -0.00235(19) 0.00919(11) -0.00002(19)
F9 0.0429(13) 0.0214(11) 0.0227(10) 0.0052(8) 0.0092(9) 0.0077(9)
F10 0.0548(14) 0.0338(12) 0.0175(10) 0.0043(9) 0.0154(10) 0.0040(10)
F12 0.0449(15) 0.0157(11) 0.0265(13) -0.0052(9) 0.0046(11) 0.0032(10)
F13 0.0512(13) 0.0173(10) 0.0228(11) 0.0020(8) 0.0141(10) -0.0033(8)
N1 0.0153(13) 0.0174(13) 0.0147(13) -0.0009(11) 0.0031(11) -0.0011(11)
C1 0.0172(17) 0.0233(19) 0.0255(19) -0.0031(15) 0.0051(15) -0.0097(14)
C2 0.031(2) 0.022(2) 0.029(2) 0.0002(14) 0.0104(17) -0.0047(14)
C3 0.0224(19) 0.0218(19) 0.0192(17) 0.0000(14) -0.0019(16) 0.0066(14)
C4 0.026(2) 0.032(2) 0.030(2) -0.0072(17) -0.0037(17) 0.0077(16)
C5 0.0230(17) 0.0205(18) 0.0173(17) -0.0051(14) 0.0069(15) 0.0013(14)
C6 0.034(2) 0.0244(19) 0.0228(19) 0.0022(15) 0.0147(16) 0.0009(15)
C7 0.0147(16) 0.0208(17) 0.0138(16) -0.0009(14) 0.0006(13) -0.0034(13)
C8 0.0145(15) 0.0180(17) 0.0174(16) -0.0040(13) 0.0047(13) -0.0024(12)
C9 0.0216(18) 0.0183(18) 0.0195(18) -0.0024(15) 0.0020(15) 0.0006(14)
C10 0.0243(18) 0.0268(19) 0.0147(17) 0.0027(14) 0.0061(15) 0.0019(15)
C11 0.0168(17) 0.030(2) 0.0184(18) -0.0088(15) 0.0015(14) -0.0023(14)
C12 0.024(2) 0.0147(17) 0.019(2) -0.0066(14) 0.0003(16) -0.0003(14)
C13 0.0217(18) 0.0212(18) 0.0162(17) 0.0051(14) 0.0011(15) -0.0017(14)
O14 0.0402(16) 0.0324(15) 0.0271(15) 0.0030(12) 0.0045(13) 0.0024(12)
N16 0.0199(15) 0.0217(16) 0.0273(16) -0.0002(12) 0.0023(13) -0.0004(12)
C15 0.0195(17) 0.0232(19) 0.029(2) -0.0008(17) 0.0022(16) -0.0008(14)
C17 0.0327(19) 0.039(3) 0.0298(18) -0.0078(17) 0.0042(16) 0.0014(17)
C18 0.036(2) 0.037(2) 0.032(2) 0.0097(18) 0.0086(19) -0.0028(17)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F9 C9 1.352(4) . ?
F10 C10 1.349(4) . ?
F12 C12 1.348(4) . ?
F13 C13 1.356(4) . ?
N1 C5 1.510(4) . ?
N1 C7 1.524(4) . ?
N1 C1 1.527(4) . ?
N1 C3 1.533(4) . ?
C1 C2 1.507(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.517(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.515(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.505(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.380(5) . ?
C8 C13 1.392(5) . ?
C9 C10 1.371(5) . ?
C10 C11 1.374(5) . ?
C11 C12 1.366(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(5) . ?
O14 C15 1.239(4) . ?
N16 C15 1.329(5) . ?
N16 C18 1.455(5) . ?
N16 C17 1.462(5) . ?
C15 H15 0.899(19) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C7 107.1(2) . . ?
C5 N1 C1 110.1(3) . . ?
C7 N1 C1 111.2(2) . . ?
C5 N1 C3 112.0(2) . . ?
C7 N1 C3 108.4(2) . . ?
C1 N1 C3 108.1(3) . . ?
C2 C1 N1 115.1(3) . . ?
C2 C1 H1A 108.5 . . ?
N1 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
N1 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 N1 113.8(3) . . ?
C4 C3 H3A 108.8 . . ?
N1 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
N1 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C6 114.5(3) . . ?
N1 C5 H5A 108.6 . . ?
C6 C5 H5A 108.6 . . ?
N1 C5 H5B 108.6 . . ?
C6 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N1 116.7(3) . . ?
C8 C7 H7A 108.1 . . ?
N1 C7 H7A 108.1 . . ?
C8 C7 H7B 108.1 . . ?
N1 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
C9 C8 C13 115.3(3) . . ?
C9 C8 C7 122.7(3) . . ?
C13 C8 C7 121.6(3) . . ?
F9 C9 C10 118.0(3) . . ?
F9 C9 C8 119.6(3) . . ?
C10 C9 C8 122.4(3) . . ?
F10 C10 C9 118.9(3) . . ?
F10 C10 C11 119.5(3) . . ?
C9 C10 C11 121.6(3) . . ?
C12 C11 C10 117.3(3) . . ?
C12 C11 H11 121.4 . . ?
C10 C11 H11 121.4 . . ?
F12 C12 C11 121.0(4) . . ?
F12 C12 C13 117.8(4) . . ?
C11 C12 C13 121.2(3) . . ?
F13 C13 C12 118.9(3) . . ?
F13 C13 C8 118.8(3) . . ?
C12 C13 C8 122.2(3) . . ?
C15 N16 C18 121.6(3) . . ?
C15 N16 C17 121.6(3) . . ?
C18 N16 C17 116.7(3) . . ?
O14 C15 N16 125.2(3) . . ?
O14 C15 H15 119(2) . . ?
N16 C15 H15 115(2) . . ?
N16 C17 H17A 109.5 . . ?
N16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N16 C18 H18A 109.5 . . ?
N16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -47.4(3) . . . . ?
C7 N1 C1 C2 71.2(4) . . . . ?
C3 N1 C1 C2 -169.9(3) . . . . ?
C5 N1 C3 C4 -53.1(4) . . . . ?
C7 N1 C3 C4 -171.1(3) . . . . ?
C1 N1 C3 C4 68.3(4) . . . . ?
C7 N1 C5 C6 64.7(3) . . . . ?
C1 N1 C5 C6 -174.2(3) . . . . ?
C3 N1 C5 C6 -54.0(4) . . . . ?
C5 N1 C7 C8 178.9(3) . . . . ?
C1 N1 C7 C8 58.6(4) . . . . ?
C3 N1 C7 C8 -60.1(3) . . . . ?
N1 C7 C8 C9 -93.3(4) . . . . ?
N1 C7 C8 C13 94.6(4) . . . . ?
C13 C8 C9 F9 178.3(3) . . . . ?
C7 C8 C9 F9 5.8(5) . . . . ?
C13 C8 C9 C10 -0.1(5) . . . . ?
C7 C8 C9 C10 -172.6(3) . . . . ?
F9 C9 C10 F10 1.6(5) . . . . ?
C8 C9 C10 F10 180.0(3) . . . . ?
F9 C9 C10 C11 -178.4(3) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
F10 C10 C11 C12 180.0(3) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
C10 C11 C12 F12 179.3(4) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
F12 C12 C13 F13 -0.9(5) . . . . ?
C11 C12 C13 F13 178.3(3) . . . . ?
F12 C12 C13 C8 -179.5(3) . . . . ?
C11 C12 C13 C8 -0.3(6) . . . . ?
C9 C8 C13 F13 -178.3(3) . . . . ?
C7 C8 C13 F13 -5.7(5) . . . . ?
C9 C8 C13 C12 0.2(5) . . . . ?
C7 C8 C13 C12 172.8(3) . . . . ?
C18 N16 C15 O14 178.3(3) . . . . ?
C17 N16 C15 O14 2.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.058

_iucr_refine_instructions_details 
;
TITL mm-208 in P 21
CELL   0.71073   7.6426  11.6845  10.7767  90.000 107.346  90.000
ZERR     2       0.0002   0.0003   0.0003   0.000   0.001   0.000
LATT -1
SYMM -X,1/2+Y,-Z
SFAC        C       H       N       O       F       BR
UNIT        32      50      4       2       8        2
L.S.      10
OMIT -3 50
OMIT 5 -1 7
TEMP  -150
SIZE  0.30 0.20 0.08
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.000000    0.255700
FVAR       0.70908
BR1   6    0.330415    0.609091    0.237502    11.00000    0.02159    0.02348 =
         0.02334   -0.00235    0.00919   -0.00002
F9    5    0.073121    0.994164    0.592661    11.00000    0.04290    0.02138 =
         0.02268    0.00523    0.00917    0.00770
F10   5    0.152950    0.883340    0.400970    11.00000    0.05483    0.03384 =
         0.01748    0.00427    0.01542    0.00402
F12   5    0.239656    0.542665    0.645909    11.00000    0.04488    0.01573 =
         0.02655   -0.00516    0.00460    0.00322
F13   5    0.161028    0.653108    0.838833    11.00000    0.05124    0.01729 =
         0.02281    0.00199    0.01413   -0.00334
N1    3    0.201361    0.946308    0.936020    11.00000    0.01532    0.01737 =
         0.01473   -0.00088    0.00310   -0.00113
C1    1    0.300387    1.038366    0.881943    11.00000    0.01724    0.02335 =
         0.02551   -0.00308    0.00508   -0.00966
AFIX  23
H1A   2    0.411355    1.062042    0.951640    11.00000   -1.20000
H1B   2    0.341317    1.004309    0.811175    11.00000   -1.20000
AFIX   0
C2    1    0.188307    1.143545    0.830063    11.00000    0.03137    0.02201 =
         0.02929    0.00016    0.01041   -0.00471
AFIX 137
H2A   2    0.061322    1.121182    0.786108    11.00000   -1.50000
H2B   2    0.239455    1.182500    0.768168    11.00000   -1.50000
H2C   2    0.191258    1.195348    0.902177    11.00000   -1.50000
AFIX   0
C3    1    0.343254    0.856824    1.006083    11.00000    0.02236    0.02179 =
         0.01917    0.00001   -0.00186    0.00659
AFIX  23
H3A   2    0.278193    0.790209    1.028145    11.00000   -1.20000
H3B   2    0.410406    0.829978    0.945947    11.00000   -1.20000
AFIX   0
C4    1    0.480627    0.900825    1.129359    11.00000    0.02628    0.03159 =
         0.02951   -0.00719   -0.00374    0.00770
AFIX  33
H4A   2    0.566369    0.839435    1.169177    11.00000   -1.50000
H4B   2    0.415714    0.926141    1.190369    11.00000   -1.50000
H4C   2    0.548570    0.965333    1.108194    11.00000   -1.50000
AFIX   0
C5    1    0.105394    0.999670    1.025555    11.00000    0.02298    0.02047 =
         0.01731   -0.00513    0.00691    0.00130
AFIX  23
H5A   2    0.009075    1.052045    0.974153    11.00000   -1.20000
H5B   2    0.195222    1.046250    1.091356    11.00000   -1.20000
AFIX   0
C6    1    0.018173    0.914530    1.095234    11.00000    0.03448    0.02435 =
         0.02276    0.00219    0.01469    0.00086
AFIX  33
H6A   2   -0.041967    0.955762    1.150442    11.00000   -1.50000
H6B   2    0.112930    0.863982    1.149202    11.00000   -1.50000
H6C   2   -0.072849    0.868787    1.031119    11.00000   -1.50000
AFIX   0
C7    1    0.055110    0.886745    0.827433    11.00000    0.01467    0.02076 =
         0.01381   -0.00091    0.00059   -0.00339
AFIX  23
H7A   2   -0.005830    0.828791    0.867361    11.00000   -1.20000
H7B   2   -0.038642    0.944230    0.784658    11.00000   -1.20000
AFIX   0
C8    1    0.118911    0.828543    0.724013    11.00000    0.01447    0.01799 =
         0.01742   -0.00400    0.00470   -0.00238
C9    1    0.117903    0.882073    0.609673    11.00000    0.02156    0.01828 =
         0.01948   -0.00235    0.00197    0.00064
C10   1    0.156731    0.825086    0.509818    11.00000    0.02433    0.02682 =
         0.01470    0.00266    0.00608    0.00190
C11   1    0.199134    0.710474    0.518247    11.00000    0.01681    0.03021 =
         0.01839   -0.00882    0.00151   -0.00233
AFIX  43
H11   2    0.225931    0.671218    0.448877    11.00000   -1.20000
AFIX   0
C12   1    0.201178    0.655312    0.630415    11.00000    0.02408    0.01469 =
         0.01908   -0.00658    0.00025   -0.00026
C13   1    0.161821    0.712447    0.730871    11.00000    0.02170    0.02123 =
         0.01623    0.00509    0.00115   -0.00166
MOLE 2
O14   4    0.625308    0.721680    0.826461    11.00000    0.04024    0.03241 =
         0.02712    0.00298    0.00454    0.00237
N16   3    0.645332    0.751729    0.622077    11.00000    0.01988    0.02167 =
         0.02734   -0.00016    0.00226   -0.00038
C15   1    0.618603    0.784975    0.732963    11.00000    0.01946    0.02315 =
         0.02878   -0.00082    0.00221   -0.00076
H15   2    0.596129    0.860025    0.738348    11.00000   -1.20000
DFIX 0.9 C15 H15
C17   1    0.679791    0.631947    0.597984    11.00000    0.03265    0.03875 =
         0.02985   -0.00777    0.00419    0.00137
AFIX 137
H17A  2    0.656895    0.583931    0.666075    11.00000   -1.50000
H17B  2    0.807544    0.622955    0.598617    11.00000   -1.50000
H17C  2    0.598038    0.608645    0.513107    11.00000   -1.50000
AFIX   0
C18   1    0.629882    0.831398    0.515611    11.00000    0.03604    0.03666 =
         0.03229    0.00970    0.00856   -0.00278
AFIX 137
H18A  2    0.613376    0.909196    0.544208    11.00000   -1.50000
H18B  2    0.524158    0.810526    0.441919    11.00000   -1.50000
H18C  2    0.741703    0.828144    0.488981    11.00000   -1.50000
 
HKLF   4
 
REM  mm-208 in P 21
REM R1 =  0.0295 for   2933 Fo > 4sig(Fo)  and  0.0347 for all   3178 data
REM    223 parameters refined using      2 restraints
 
END
 
WGHT      0.0000      0.2589
REM Highest difference peak  0.229,  deepest hole -0.267,  1-sigma level  0.058
Q1    1   0.4549  0.6249  0.5232  11.00000  0.05    0.23
Q2    1  -0.1408  1.1568  0.9609  11.00000  0.05    0.22
Q3    1   0.5038  0.6009  0.1995  11.00000  0.05    0.22
Q4    1   0.1231  0.7395  0.5043  11.00000  0.05    0.22
Q5    1   0.2059  0.6128  0.9595  11.00000  0.05    0.22
Q6    1   0.0725  0.8367  1.1256  11.00000  0.05    0.21
Q7    1   0.6373  0.6470  0.8136  11.00000  0.05    0.21
Q8    1   0.2625  0.6106  0.8037  11.00000  0.05    0.21
Q9    1  -0.1486  0.8939  1.0159  11.00000  0.05    0.20
Q10   1   0.2369  1.0665  0.8633  11.00000  0.05    0.20
Q11   1   0.4684  0.5377  0.6681  11.00000  0.05    0.20
Q12   1  -0.1399  1.0695  0.9645  11.00000  0.05    0.19
Q13   1   0.0099  1.1115  0.7244  11.00000  0.05    0.19
Q14   1   0.4266  0.7689  1.1410  11.00000  0.05    0.19
Q15   1   0.3803  0.7341  0.7416  11.00000  0.05    0.18
Q16   1   0.0900  1.1242  0.5354  11.00000  0.05    0.18
Q17   1   0.1670  1.0610  1.0487  11.00000  0.05    0.18
Q18   1   0.1432  0.6261  0.1652  11.00000  0.05    0.18
Q19   1  -0.1740  0.8685  0.7985  11.00000  0.05    0.18
Q20   1   0.3565  0.9866  0.6980  11.00000  0.05    0.18
Q21   1   0.2341  0.5808  0.3814  11.00000  0.05    0.18
Q22   1   0.1425  1.0595  1.2239  11.00000  0.05    0.18
Q23   1   0.0032  0.9372  1.1756  11.00000  0.05    0.17
Q24   1   0.3880  0.8066  0.3917  11.00000  0.05    0.17
Q25   1   0.1568  0.6819  0.7810  11.00000  0.05    0.17

;
_database_code_depnum_ccdc_archive 'CCDC 1005281'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-yl-012-2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H16 F5 N2, Br'
_chemical_formula_sum            'C13 H16 Br F5 N2'
_chemical_formula_weight         375.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.8555(2)
_cell_length_b                   18.5382(5)
_cell_length_c                   8.9536(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.773(2)
_cell_angle_gamma                90.00
_cell_volume                     1464.77(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3656
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    2.855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4435
_exptl_absorpt_correction_T_max  0.8704
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8527
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2579
_reflns_number_gt                2116
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+7.6442P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2579
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_restrained_S_all      1.242
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.66400(6) 0.25107(4) 0.40931(6) 0.02899(18) Uani 1 1 d . . .
F7 F 0.3554(4) 0.36127(18) 0.2512(4) 0.0300(8) Uani 1 1 d . . .
F8 F 0.1962(4) 0.46319(19) 0.0957(4) 0.0379(9) Uani 1 1 d . . .
F9 F -0.0702(4) 0.51175(18) 0.1900(4) 0.0389(9) Uani 1 1 d . . .
F10 F -0.1750(4) 0.45636(18) 0.4417(4) 0.0370(9) Uani 1 1 d . . .
F11 F -0.0140(3) 0.35537(17) 0.6006(4) 0.0283(7) Uani 1 1 d . . .
N1 N 0.2190(5) 0.2173(2) 0.4682(5) 0.0189(10) Uani 1 1 d . . .
N2 N 0.0231(5) 0.1253(2) 0.2725(5) 0.0241(10) Uani 1 1 d . . .
C1 C 0.2413(6) 0.2060(3) 0.3039(6) 0.0209(12) Uani 1 1 d . . .
H1A H 0.3505 0.2098 0.2890 0.025 Uiso 1 1 calc R . .
H1B H 0.1874 0.2444 0.2441 0.025 Uiso 1 1 calc R . .
C2 C 0.1829(6) 0.1326(3) 0.2480(6) 0.0213(12) Uani 1 1 d . . .
H2A H 0.1964 0.1278 0.1398 0.026 Uiso 1 1 calc R . .
H2B H 0.2417 0.0939 0.3020 0.026 Uiso 1 1 calc R . .
C3 C 0.0031(6) 0.1292(3) 0.4320(6) 0.0253(13) Uani 1 1 d . . .
H3A H 0.0627 0.0906 0.4857 0.030 Uiso 1 1 calc R . .
H3B H -0.1051 0.1219 0.4483 0.030 Uiso 1 1 calc R . .
C4 C 0.0548(6) 0.2019(3) 0.4928(6) 0.0216(12) Uani 1 1 d . . .
H4A H 0.0418 0.2037 0.6015 0.026 Uiso 1 1 calc R . .
H4B H -0.0099 0.2400 0.4433 0.026 Uiso 1 1 calc R . .
C5 C 0.2614(6) 0.2945(3) 0.5147(6) 0.0226(12) Uani 1 1 d . . .
H5A H 0.2455 0.3007 0.6221 0.027 Uiso 1 1 calc R . .
H5B H 0.3707 0.3018 0.5034 0.027 Uiso 1 1 calc R . .
C6 C 0.1735(6) 0.3513(3) 0.4266(6) 0.0198(11) Uani 1 1 d . . .
C7 C 0.2235(6) 0.3822(3) 0.2988(6) 0.0242(12) Uani 1 1 d . . .
C8 C 0.1438(7) 0.4353(3) 0.2202(6) 0.0262(13) Uani 1 1 d . . .
C9 C 0.0096(7) 0.4597(3) 0.2673(6) 0.0265(13) Uani 1 1 d . . .
C10 C -0.0444(6) 0.4310(3) 0.3938(6) 0.0240(12) Uani 1 1 d . . .
C11 C 0.0379(6) 0.3789(3) 0.4736(6) 0.0227(12) Uani 1 1 d . . .
C12 C 0.3230(6) 0.1688(3) 0.5648(6) 0.0257(12) Uani 1 1 d . . .
H12A H 0.3072 0.1769 0.6705 0.038 Uiso 1 1 calc R . .
H12B H 0.4285 0.1797 0.5477 0.038 Uiso 1 1 calc R . .
H12C H 0.3009 0.1184 0.5388 0.038 Uiso 1 1 calc R . .
C13 C -0.0401(7) 0.0586(3) 0.2051(7) 0.0345(15) Uani 1 1 d . . .
H13A H -0.1470 0.0545 0.2247 0.052 Uiso 1 1 calc R . .
H13B H 0.0161 0.0171 0.2488 0.052 Uiso 1 1 calc R . .
H13C H -0.0316 0.0597 0.0967 0.052 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0179(3) 0.0485(4) 0.0203(3) -0.0058(3) 0.00066(19) 0.0028(3)
F7 0.0313(18) 0.0302(18) 0.0303(18) 0.0030(15) 0.0124(14) 0.0025(15)
F8 0.057(2) 0.0310(19) 0.0267(19) 0.0106(15) 0.0089(17) -0.0002(17)
F9 0.047(2) 0.0292(19) 0.038(2) 0.0070(16) -0.0111(17) 0.0125(17)
F10 0.0286(18) 0.0304(19) 0.052(2) -0.0022(17) 0.0009(16) 0.0103(15)
F11 0.0270(17) 0.0291(18) 0.0302(18) 0.0031(14) 0.0104(14) 0.0050(14)
N1 0.019(2) 0.021(2) 0.017(2) 0.0026(18) 0.0051(18) -0.0005(18)
N2 0.021(2) 0.022(2) 0.029(3) 0.000(2) 0.0009(19) -0.005(2)
C1 0.018(3) 0.025(3) 0.020(3) 0.002(2) 0.002(2) -0.001(2)
C2 0.020(3) 0.019(3) 0.026(3) -0.001(2) 0.008(2) 0.000(2)
C3 0.024(3) 0.027(3) 0.025(3) 0.005(2) 0.006(2) -0.004(2)
C4 0.018(3) 0.027(3) 0.020(3) 0.002(2) 0.004(2) 0.001(2)
C5 0.022(3) 0.022(3) 0.024(3) 0.002(2) 0.004(2) 0.001(2)
C6 0.023(3) 0.018(3) 0.017(3) 0.000(2) -0.001(2) -0.003(2)
C7 0.024(3) 0.020(3) 0.029(3) -0.005(2) 0.002(2) -0.004(2)
C8 0.038(3) 0.021(3) 0.020(3) 0.000(2) 0.001(2) -0.007(3)
C9 0.032(3) 0.020(3) 0.025(3) 0.000(2) -0.010(2) 0.004(3)
C10 0.020(3) 0.017(3) 0.034(3) -0.005(2) -0.001(2) 0.003(2)
C11 0.021(3) 0.025(3) 0.023(3) 0.000(2) 0.005(2) 0.001(2)
C12 0.028(3) 0.025(3) 0.022(3) 0.003(2) -0.002(2) 0.003(3)
C13 0.035(3) 0.027(3) 0.040(4) -0.010(3) 0.000(3) -0.012(3)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F7 C7 1.333(6) . ?
F8 C8 1.346(6) . ?
F9 C9 1.351(6) . ?
F10 C10 1.351(6) . ?
F11 C11 1.335(6) . ?
N1 C12 1.506(7) . ?
N1 C4 1.515(6) . ?
N1 C1 1.515(7) . ?
N1 C5 1.529(7) . ?
N2 C3 1.455(7) . ?
N2 C2 1.457(7) . ?
N2 C13 1.466(7) . ?
C1 C2 1.524(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.511(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.495(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.385(8) . ?
C6 C11 1.402(8) . ?
C7 C8 1.372(8) . ?
C8 C9 1.370(8) . ?
C9 C10 1.373(8) . ?
C10 C11 1.375(8) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 C4 110.7(4) . . ?
C12 N1 C1 110.6(4) . . ?
C4 N1 C1 108.6(4) . . ?
C12 N1 C5 106.1(4) . . ?
C4 N1 C5 110.7(4) . . ?
C1 N1 C5 110.2(4) . . ?
C3 N2 C2 110.1(4) . . ?
C3 N2 C13 111.9(5) . . ?
C2 N2 C13 111.0(4) . . ?
N1 C1 C2 112.0(4) . . ?
N1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
N2 C2 C1 109.9(4) . . ?
N2 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
N2 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
N2 C3 C4 109.9(4) . . ?
N2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
N2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C3 C4 N1 112.4(4) . . ?
C3 C4 H4A 109.1 . . ?
N1 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
N1 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 N1 114.2(4) . . ?
C6 C5 H5A 108.7 . . ?
N1 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
N1 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C7 C6 C11 116.0(5) . . ?
C7 C6 C5 122.6(5) . . ?
C11 C6 C5 121.4(5) . . ?
F7 C7 C8 118.2(5) . . ?
F7 C7 C6 119.5(5) . . ?
C8 C7 C6 122.3(5) . . ?
F8 C8 C9 119.7(5) . . ?
F8 C8 C7 120.1(5) . . ?
C9 C8 C7 120.2(5) . . ?
F9 C9 C8 120.5(5) . . ?
F9 C9 C10 119.7(5) . . ?
C8 C9 C10 119.7(5) . . ?
F10 C10 C9 119.6(5) . . ?
F10 C10 C11 120.7(5) . . ?
C9 C10 C11 119.7(5) . . ?
F11 C11 C10 117.8(5) . . ?
F11 C11 C6 120.1(5) . . ?
C10 C11 C6 122.1(5) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C1 C2 69.8(5) . . . . ?
C4 N1 C1 C2 -51.9(5) . . . . ?
C5 N1 C1 C2 -173.3(4) . . . . ?
C3 N2 C2 C1 -61.8(6) . . . . ?
C13 N2 C2 C1 173.8(5) . . . . ?
N1 C1 C2 N2 57.5(6) . . . . ?
C2 N2 C3 C4 62.0(6) . . . . ?
C13 N2 C3 C4 -174.1(5) . . . . ?
N2 C3 C4 N1 -58.1(6) . . . . ?
C12 N1 C4 C3 -69.2(5) . . . . ?
C1 N1 C4 C3 52.4(5) . . . . ?
C5 N1 C4 C3 173.4(4) . . . . ?
C12 N1 C5 C6 177.9(5) . . . . ?
C4 N1 C5 C6 -62.0(6) . . . . ?
C1 N1 C5 C6 58.1(6) . . . . ?
N1 C5 C6 C7 -92.2(6) . . . . ?
N1 C5 C6 C11 90.9(6) . . . . ?
C11 C6 C7 F7 176.7(5) . . . . ?
C5 C6 C7 F7 -0.3(8) . . . . ?
C11 C6 C7 C8 -1.6(8) . . . . ?
C5 C6 C7 C8 -178.6(5) . . . . ?
F7 C7 C8 F8 2.3(8) . . . . ?
C6 C7 C8 F8 -179.3(5) . . . . ?
F7 C7 C8 C9 -178.3(5) . . . . ?
C6 C7 C8 C9 0.0(8) . . . . ?
F8 C8 C9 F9 -0.2(8) . . . . ?
C7 C8 C9 F9 -179.5(5) . . . . ?
F8 C8 C9 C10 179.6(5) . . . . ?
C7 C8 C9 C10 0.3(8) . . . . ?
F9 C9 C10 F10 -1.6(8) . . . . ?
C8 C9 C10 F10 178.5(5) . . . . ?
F9 C9 C10 C11 -179.1(5) . . . . ?
C8 C9 C10 C11 1.1(8) . . . . ?
F10 C10 C11 F11 -1.3(8) . . . . ?
C9 C10 C11 F11 176.2(5) . . . . ?
F10 C10 C11 C6 179.7(5) . . . . ?
C9 C10 C11 C6 -2.8(8) . . . . ?
C7 C6 C11 F11 -175.9(5) . . . . ?
C5 C6 C11 F11 1.1(8) . . . . ?
C7 C6 C11 C10 3.0(8) . . . . ?
C5 C6 C11 C10 -180.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.093

_iucr_refine_instructions_details 
;
TITL mm-yl-012-2 in P 21/n
CELL   0.71073   8.8555  18.5382   8.9536  90.000  94.773  90.000
ZERR     4       0.0002   0.0005   0.0002   0.000   0.002   0.000
LATT  1
SYMM 1/2-X,1/2+Y,1/2-Z
SFAC        C       H       N       F       BR
UNIT        52      64       8      20       4
L.S.      10
OMIT -3 50.05
OMIT 0 3 1
OMIT 2 6 3
OMIT 3 7 2
OMIT 2 3 1
OMIT 3 8 2
OMIT -1 2 4
OMIT -2 5 3
OMIT -4 3 1
OMIT -1 4 4
OMIT 1 3 4
OMIT 2 4 1
OMIT 4 1 1
TEMP  -150
SIZE  0.34 0.07 0.05
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.000000    7.644200
FVAR       0.44721
BR1   5    0.663996    0.251073    0.409306    11.00000    0.01795    0.04853 =
         0.02034   -0.00583    0.00066    0.00283
F7    4    0.355417    0.361268    0.251195    11.00000    0.03131    0.03020 =
         0.03028    0.00297    0.01243    0.00252
F8    4    0.196221    0.463188    0.095714    11.00000    0.05688    0.03096 =
         0.02669    0.01061    0.00887   -0.00022
F9    4   -0.070221    0.511745    0.189956    11.00000    0.04696    0.02920 =
         0.03801    0.00697   -0.01114    0.01248
F10   4   -0.175025    0.456361    0.441731    11.00000    0.02860    0.03036 =
         0.05167   -0.00216    0.00094    0.01035
F11   4   -0.014021    0.355370    0.600625    11.00000    0.02698    0.02909 =
         0.03023    0.00309    0.01038    0.00502
N1    3    0.218981    0.217286    0.468243    11.00000    0.01943    0.02075 =
         0.01714    0.00258    0.00505   -0.00052
N2    3    0.023117    0.125300    0.272531    11.00000    0.02113    0.02249 =
         0.02861   -0.00044    0.00094   -0.00455
C1    1    0.241318    0.205955    0.303910    11.00000    0.01794    0.02527 =
         0.01957    0.00179    0.00198   -0.00112
AFIX  23
H1A   2    0.350537    0.209842    0.288963    11.00000   -1.20000
H1B   2    0.187367    0.244398    0.244127    11.00000   -1.20000
AFIX   0
C2    1    0.182934    0.132640    0.247974    11.00000    0.02030    0.01873 =
         0.02592   -0.00138    0.00764    0.00033
AFIX  23
H2A   2    0.196360    0.127843    0.139754    11.00000   -1.20000
H2B   2    0.241749    0.093864    0.302004    11.00000   -1.20000
AFIX   0
C3    1    0.003072    0.129195    0.431974    11.00000    0.02438    0.02706 =
         0.02510    0.00532    0.00556   -0.00369
AFIX  23
H3A   2    0.062680    0.090575    0.485669    11.00000   -1.20000
H3B   2   -0.105053    0.121868    0.448346    11.00000   -1.20000
AFIX   0
C4    1    0.054800    0.201945    0.492816    11.00000    0.01758    0.02744 =
         0.02029    0.00236    0.00413    0.00086
AFIX  23
H4A   2    0.041839    0.203723    0.601517    11.00000   -1.20000
H4B   2   -0.009886    0.239995    0.443281    11.00000   -1.20000
AFIX   0
C5    1    0.261441    0.294503    0.514680    11.00000    0.02238    0.02154 =
         0.02414    0.00163    0.00421    0.00143
AFIX  23
H5A   2    0.245456    0.300686    0.622055    11.00000   -1.20000
H5B   2    0.370658    0.301810    0.503436    11.00000   -1.20000
AFIX   0
C6    1    0.173477    0.351257    0.426576    11.00000    0.02340    0.01818 =
         0.01725    0.00034   -0.00143   -0.00284
C7    1    0.223533    0.382156    0.298763    11.00000    0.02367    0.02003 =
         0.02877   -0.00463    0.00171   -0.00399
C8    1    0.143788    0.435319    0.220204    11.00000    0.03754    0.02072 =
         0.02010    0.00043    0.00101   -0.00719
C9    1    0.009601    0.459749    0.267265    11.00000    0.03183    0.02047 =
         0.02503   -0.00037   -0.01045    0.00442
C10   1   -0.044396    0.431036    0.393768    11.00000    0.02047    0.01697 =
         0.03410   -0.00481   -0.00100    0.00276
C11   1    0.037902    0.378869    0.473553    11.00000    0.02142    0.02458 =
         0.02270   -0.00043    0.00519    0.00100
C12   1    0.322963    0.168838    0.564751    11.00000    0.02832    0.02545 =
         0.02247    0.00256   -0.00213    0.00331
AFIX  33
H12A  2    0.307181    0.176937    0.670489    11.00000   -1.50000
H12B  2    0.428463    0.179703    0.547712    11.00000   -1.50000
H12C  2    0.300897    0.118352    0.538843    11.00000   -1.50000
AFIX   0
C13   1   -0.040091    0.058641    0.205091    11.00000    0.03525    0.02731 =
         0.04045   -0.00994    0.00019   -0.01243
AFIX  33
H13A  2   -0.146997    0.054529    0.224666    11.00000   -1.50000
H13B  2    0.016095    0.017143    0.248844    11.00000   -1.50000
H13C  2   -0.031627    0.059684    0.096674    11.00000   -1.50000
HKLF   4
 
REM  mm-yl-012-2 in P 21/n
REM R1 =  0.0504 for   2116 Fo > 4sig(Fo)  and  0.0637 for all   2579 data
REM    190 parameters refined using      0 restraints
 
END
 
WGHT      0.0000      7.6376
REM Highest difference peak  0.403,  deepest hole -0.387,  1-sigma level  0.093
Q1    1   0.7511  0.2803  0.4692  11.00000  0.05    0.40
Q2    1  -0.1356  0.0417  0.4539  11.00000  0.05    0.40
Q3    1   0.0034  0.3708  0.2397  11.00000  0.05    0.38
Q4    1   0.1629  0.0420  0.0516  11.00000  0.05    0.36
Q5    1   0.4188  0.1569  0.4547  11.00000  0.05    0.35
Q6    1  -0.0929  0.0614  0.1012  11.00000  0.05    0.35
Q7    1   0.1956  0.3245  0.2901  11.00000  0.05    0.34
Q8    1   0.3206  0.4595  0.2313  11.00000  0.05    0.34
Q9    1   0.0320  0.4288  0.4602  11.00000  0.05    0.33
Q10   1   0.3556  0.1499  0.2277  11.00000  0.05    0.33
Q11   1  -0.1710  0.2349  0.5375  11.00000  0.05    0.32
Q12   1   0.1391  0.0675  0.1869  11.00000  0.05    0.32
Q13   1   0.0345  0.1335  0.6154  11.00000  0.05    0.32
Q14   1  -0.2095  0.1266  0.3352  11.00000  0.05    0.32
Q15   1   0.1025  0.1217 -0.0782  11.00000  0.05    0.31
Q16   1   0.0793 -0.0273  0.3425  11.00000  0.05    0.30
Q17   1   0.5924  0.3915  0.3620  11.00000  0.05    0.30
Q18   1   0.0175  0.0631  0.1152  11.00000  0.05    0.29
Q19   1  -0.0692  0.0566 -0.0844  11.00000  0.05    0.28
Q20   1  -0.1421  0.3296  0.4658  11.00000  0.05    0.27
Q21   1  -0.0317  0.0394  0.3780  11.00000  0.05    0.27
Q22   1   0.0807  0.2015  0.7176  11.00000  0.05    0.27
Q23   1   0.1903  0.2952  0.7716  11.00000  0.05    0.27
Q24   1   0.0561  0.2226  0.1461  11.00000  0.05    0.27
Q25   1   0.1448  0.0904  0.7448  11.00000  0.05    0.26
;
_database_code_depnum_ccdc_archive 'CCDC 1005282'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-om-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H9 F10 N2, H2 O, Br'
_chemical_formula_sum            'C21 H11 Br F10 N2 O'
_chemical_formula_weight         577.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.4829(3)
_cell_length_b                   16.1450(4)
_cell_length_c                   10.3729(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.5290(10)
_cell_angle_gamma                90.00
_cell_volume                     2089.77(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5245
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    2.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6251
_exptl_absorpt_correction_T_max  0.7600
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26660
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3690
_reflns_number_gt                2990
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2006)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0942P)^2^+10.9283P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3690
_refine_ls_number_parameters     328
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1818
_refine_ls_wR_factor_gt          0.1701
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.01102(5) 0.30884(4) 0.09202(6) 0.0320(2) Uani 1 1 d . . .
F10 F 0.8384(3) 0.67863(18) 0.1679(3) 0.0232(7) Uani 1 1 d . . .
F11 F 0.6779(3) 0.7377(2) 0.0171(4) 0.0354(8) Uani 1 1 d . . .
F12 F 0.5506(3) 0.6319(3) -0.1214(4) 0.0457(10) Uani 1 1 d . . .
F13 F 0.5909(3) 0.4657(3) -0.1141(4) 0.0468(10) Uani 1 1 d . . .
F14 F 0.7578(3) 0.4074(2) 0.0286(3) 0.0327(8) Uani 1 1 d . . .
F17 F 0.6784(3) 0.2530(2) 0.7204(3) 0.0329(8) Uani 1 1 d . . .
F18 F 0.4825(3) 0.2915(3) 0.8012(4) 0.0468(11) Uani 1 1 d . . .
F19 F 0.3493(3) 0.3872(2) 0.6514(4) 0.0442(10) Uani 1 1 d . . .
F20 F 0.4140(3) 0.4399(2) 0.4172(4) 0.0398(9) Uani 1 1 d . . .
F21 F 0.6115(3) 0.4038(2) 0.3377(3) 0.0283(8) Uani 1 1 d . . .
N1 N 0.8738(3) 0.4739(3) 0.3001(4) 0.0134(9) Uani 1 1 d . . .
N2 N 0.8184(3) 0.3842(2) 0.4396(4) 0.0128(8) Uani 1 1 d . . .
C1 C 0.8714(4) 0.5151(3) 0.4184(5) 0.0149(10) Uani 1 1 d . . .
C2 C 0.8359(4) 0.4578(3) 0.5071(5) 0.0124(10) Uani 1 1 d . . .
C3 C 0.8255(4) 0.4775(3) 0.6375(5) 0.0160(10) Uani 1 1 d . . .
H3 H 0.8022 0.4381 0.6987 0.021(15) Uiso 1 1 calc R . .
C4 C 0.8511(4) 0.5576(3) 0.6714(5) 0.0199(11) Uani 1 1 d . . .
H4 H 0.8445 0.5740 0.7588 0.019(14) Uiso 1 1 calc R . .
C5 C 0.8866(4) 0.6160(3) 0.5818(5) 0.0199(11) Uani 1 1 d . . .
H5 H 0.9035 0.6705 0.6103 0.015(14) Uiso 1 1 calc R . .
C6 C 0.8975(4) 0.5961(3) 0.4529(5) 0.0167(11) Uani 1 1 d . . .
H6 H 0.9213 0.6354 0.3917 0.017(14) Uiso 1 1 calc R . .
C7 C 0.8423(4) 0.3961(3) 0.3168(5) 0.0134(10) Uani 1 1 d . . .
H7 H 0.8376 0.3553 0.2510 0.016 Uiso 1 1 calc R . .
C8 C 0.9029(4) 0.5095(3) 0.1741(5) 0.0171(11) Uani 1 1 d . . .
H8A H 0.9385 0.4664 0.1225 0.031(17) Uiso 1 1 calc R . .
H8B H 0.9545 0.5553 0.1886 0.018(14) Uiso 1 1 calc R . .
C9 C 0.8058(4) 0.5418(3) 0.0991(5) 0.0165(11) Uani 1 1 d . . .
C10 C 0.7807(4) 0.6252(3) 0.0954(5) 0.0180(11) Uani 1 1 d . . .
C11 C 0.6975(5) 0.6556(4) 0.0207(6) 0.0258(13) Uani 1 1 d . . .
C12 C 0.6334(5) 0.6029(4) -0.0498(6) 0.0324(14) Uani 1 1 d . . .
C13 C 0.6542(5) 0.5181(4) -0.0459(6) 0.0299(13) Uani 1 1 d . . .
C14 C 0.7393(4) 0.4899(3) 0.0272(5) 0.0229(12) Uani 1 1 d . . .
C15 C 0.7665(4) 0.3093(3) 0.4909(5) 0.0143(10) Uani 1 1 d . . .
H15A H 0.8078 0.2891 0.5674 0.017 Uiso 1 1 calc R . .
H15B H 0.7660 0.2651 0.4248 0.017 Uiso 1 1 calc R . .
C16 C 0.6535(4) 0.3284(3) 0.5279(5) 0.0148(10) Uani 1 1 d . . .
C17 C 0.6154(4) 0.3007(3) 0.6433(5) 0.0218(12) Uani 1 1 d . . .
C18 C 0.5144(5) 0.3198(4) 0.6865(6) 0.0276(13) Uani 1 1 d . . .
C19 C 0.4471(4) 0.3672(4) 0.6113(6) 0.0272(13) Uani 1 1 d . . .
C20 C 0.4800(4) 0.3939(3) 0.4923(6) 0.0247(12) Uani 1 1 d . . .
C21 C 0.5822(4) 0.3748(3) 0.4522(5) 0.0184(11) Uani 1 1 d . . .
O1 O 0.9053(4) 0.1850(3) 0.3021(4) 0.0319(10) Uani 1 1 d D . .
H1A H 0.926(6) 0.181(5) 0.378(3) 0.048 Uiso 1 1 d D . .
H1B H 0.949(5) 0.201(5) 0.247(6) 0.048 Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0358(4) 0.0302(4) 0.0301(4) -0.0061(3) 0.0021(3) 0.0015(3)
F10 0.0276(17) 0.0155(15) 0.0265(17) 0.0032(13) -0.0005(13) -0.0008(12)
F11 0.037(2) 0.0268(18) 0.042(2) 0.0133(16) 0.0001(16) 0.0104(15)
F12 0.037(2) 0.055(2) 0.045(2) 0.010(2) -0.0195(17) 0.0087(18)
F13 0.043(2) 0.046(2) 0.050(2) -0.0075(19) -0.0255(19) -0.0064(18)
F14 0.038(2) 0.0194(17) 0.041(2) -0.0074(15) -0.0112(16) -0.0005(14)
F17 0.0238(17) 0.048(2) 0.0266(18) 0.0201(16) -0.0022(14) -0.0014(16)
F18 0.036(2) 0.074(3) 0.031(2) 0.0055(19) 0.0169(17) -0.009(2)
F19 0.0182(18) 0.049(2) 0.066(3) -0.018(2) 0.0133(17) 0.0029(16)
F20 0.0207(18) 0.035(2) 0.063(3) 0.0064(18) -0.0115(16) 0.0113(15)
F21 0.0223(17) 0.0345(19) 0.0278(18) 0.0137(15) -0.0067(14) 0.0038(14)
N1 0.014(2) 0.014(2) 0.013(2) -0.0014(16) 0.0012(16) 0.0007(16)
N2 0.011(2) 0.010(2) 0.018(2) 0.0033(16) -0.0014(16) -0.0012(16)
C1 0.012(2) 0.016(3) 0.017(2) 0.001(2) -0.0020(19) 0.0032(19)
C2 0.007(2) 0.012(2) 0.018(3) -0.0021(19) -0.0040(18) 0.0024(18)
C3 0.013(2) 0.018(3) 0.016(3) 0.001(2) -0.0013(19) 0.002(2)
C4 0.018(3) 0.024(3) 0.017(3) -0.006(2) -0.003(2) 0.003(2)
C5 0.021(3) 0.013(3) 0.025(3) -0.005(2) -0.008(2) 0.002(2)
C6 0.015(3) 0.009(2) 0.026(3) 0.001(2) 0.000(2) 0.0004(19)
C7 0.010(2) 0.014(2) 0.017(2) -0.001(2) -0.0022(19) 0.0024(18)
C8 0.017(3) 0.018(3) 0.017(3) 0.002(2) 0.002(2) -0.001(2)
C9 0.016(3) 0.019(3) 0.014(2) 0.004(2) 0.003(2) 0.003(2)
C10 0.019(3) 0.020(3) 0.015(2) 0.003(2) 0.005(2) -0.001(2)
C11 0.027(3) 0.022(3) 0.029(3) 0.009(2) 0.009(2) 0.008(2)
C12 0.023(3) 0.046(4) 0.028(3) 0.010(3) -0.005(2) 0.010(3)
C13 0.027(3) 0.037(3) 0.026(3) -0.002(3) -0.005(2) -0.008(3)
C14 0.024(3) 0.022(3) 0.023(3) 0.000(2) -0.001(2) 0.001(2)
C15 0.012(2) 0.009(2) 0.021(3) 0.003(2) 0.0003(19) -0.0005(18)
C16 0.012(2) 0.014(2) 0.019(3) -0.004(2) -0.001(2) -0.0013(19)
C17 0.016(3) 0.024(3) 0.025(3) 0.000(2) -0.004(2) -0.004(2)
C18 0.022(3) 0.035(3) 0.027(3) -0.007(3) 0.010(2) -0.011(2)
C19 0.013(3) 0.030(3) 0.038(3) -0.014(3) 0.007(2) -0.001(2)
C20 0.019(3) 0.016(3) 0.039(3) -0.003(2) -0.010(2) 0.004(2)
C21 0.017(3) 0.016(3) 0.022(3) 0.000(2) -0.001(2) -0.002(2)
O1 0.029(2) 0.039(3) 0.028(2) -0.006(2) -0.0031(18) -0.0007(19)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F10 C10 1.341(6) . ?
F11 C11 1.348(7) . ?
F12 C12 1.342(7) . ?
F13 C13 1.346(7) . ?
F14 C14 1.351(6) . ?
F17 C17 1.348(6) . ?
F18 C18 1.345(7) . ?
F19 C19 1.339(6) . ?
F20 C20 1.342(6) . ?
F21 C21 1.337(6) . ?
N1 C7 1.329(6) . ?
N1 C1 1.396(6) . ?
N1 C8 1.481(6) . ?
N2 C7 1.330(6) . ?
N2 C2 1.394(6) . ?
N2 C15 1.477(6) . ?
C1 C2 1.386(7) . ?
C1 C6 1.393(7) . ?
C2 C3 1.398(7) . ?
C3 C4 1.376(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.405(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(8) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.516(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.383(7) . ?
C9 C14 1.384(8) . ?
C10 C11 1.369(8) . ?
C11 C12 1.367(9) . ?
C12 C13 1.393(9) . ?
C13 C14 1.367(8) . ?
C15 C16 1.504(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.374(8) . ?
C16 C21 1.390(7) . ?
C17 C18 1.384(8) . ?
C18 C19 1.365(9) . ?
C19 C20 1.381(9) . ?
C20 C21 1.387(8) . ?
O1 H1A 0.83(2) . ?
O1 H1B 0.84(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C1 108.8(4) . . ?
C7 N1 C8 124.2(4) . . ?
C1 N1 C8 127.0(4) . . ?
C7 N2 C2 108.8(4) . . ?
C7 N2 C15 125.1(4) . . ?
C2 N2 C15 125.5(4) . . ?
C2 C1 C6 122.2(5) . . ?
C2 C1 N1 106.3(4) . . ?
C6 C1 N1 131.5(5) . . ?
C1 C2 N2 106.4(4) . . ?
C1 C2 C3 122.0(5) . . ?
N2 C2 C3 131.5(5) . . ?
C4 C3 C2 115.7(5) . . ?
C4 C3 H3 122.1 . . ?
C2 C3 H3 122.1 . . ?
C3 C4 C5 122.5(5) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C6 C5 C4 121.6(5) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C1 116.0(5) . . ?
C5 C6 H6 122.0 . . ?
C1 C6 H6 122.0 . . ?
N1 C7 N2 109.7(4) . . ?
N1 C7 H7 125.2 . . ?
N2 C7 H7 125.2 . . ?
N1 C8 C9 112.0(4) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C14 116.3(5) . . ?
C10 C9 C8 121.8(5) . . ?
C14 C9 C8 121.8(5) . . ?
F10 C10 C11 118.4(5) . . ?
F10 C10 C9 119.5(5) . . ?
C11 C10 C9 122.1(5) . . ?
F11 C11 C12 119.6(5) . . ?
F11 C11 C10 120.1(5) . . ?
C12 C11 C10 120.3(5) . . ?
F12 C12 C11 120.7(6) . . ?
F12 C12 C13 120.0(6) . . ?
C11 C12 C13 119.4(5) . . ?
F13 C13 C14 121.2(6) . . ?
F13 C13 C12 119.8(5) . . ?
C14 C13 C12 119.0(5) . . ?
F14 C14 C13 117.7(5) . . ?
F14 C14 C9 119.4(5) . . ?
C13 C14 C9 122.9(5) . . ?
N2 C15 C16 110.4(4) . . ?
N2 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
N2 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C21 115.9(5) . . ?
C17 C16 C15 120.3(5) . . ?
C21 C16 C15 123.8(5) . . ?
F17 C17 C16 119.5(5) . . ?
F17 C17 C18 117.2(5) . . ?
C16 C17 C18 123.3(5) . . ?
F18 C18 C19 120.2(5) . . ?
F18 C18 C17 120.3(6) . . ?
C19 C18 C17 119.5(5) . . ?
F19 C19 C18 120.7(6) . . ?
F19 C19 C20 119.8(5) . . ?
C18 C19 C20 119.5(5) . . ?
F20 C20 C19 120.0(5) . . ?
F20 C20 C21 120.3(5) . . ?
C19 C20 C21 119.8(5) . . ?
F21 C21 C20 117.6(5) . . ?
F21 C21 C16 120.3(5) . . ?
C20 C21 C16 122.0(5) . . ?
H1A O1 H1B 119(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C1 C2 -0.4(5) . . . . ?
C8 N1 C1 C2 177.9(4) . . . . ?
C7 N1 C1 C6 179.3(5) . . . . ?
C8 N1 C1 C6 -2.4(8) . . . . ?
C6 C1 C2 N2 -179.7(4) . . . . ?
N1 C1 C2 N2 0.1(5) . . . . ?
C6 C1 C2 C3 -0.9(7) . . . . ?
N1 C1 C2 C3 178.9(4) . . . . ?
C7 N2 C2 C1 0.2(5) . . . . ?
C15 N2 C2 C1 -171.3(4) . . . . ?
C7 N2 C2 C3 -178.4(5) . . . . ?
C15 N2 C2 C3 10.1(8) . . . . ?
C1 C2 C3 C4 0.9(7) . . . . ?
N2 C2 C3 C4 179.3(5) . . . . ?
C2 C3 C4 C5 -0.6(7) . . . . ?
C3 C4 C5 C6 0.2(8) . . . . ?
C4 C5 C6 C1 -0.2(7) . . . . ?
C2 C1 C6 C5 0.5(7) . . . . ?
N1 C1 C6 C5 -179.3(5) . . . . ?
C1 N1 C7 N2 0.6(5) . . . . ?
C8 N1 C7 N2 -177.8(4) . . . . ?
C2 N2 C7 N1 -0.5(5) . . . . ?
C15 N2 C7 N1 171.0(4) . . . . ?
C7 N1 C8 C9 86.0(6) . . . . ?
C1 N1 C8 C9 -92.0(6) . . . . ?
N1 C8 C9 C10 100.5(5) . . . . ?
N1 C8 C9 C14 -81.7(6) . . . . ?
C14 C9 C10 F10 176.7(4) . . . . ?
C8 C9 C10 F10 -5.3(7) . . . . ?
C14 C9 C10 C11 -2.7(7) . . . . ?
C8 C9 C10 C11 175.3(5) . . . . ?
F10 C10 C11 F11 2.6(7) . . . . ?
C9 C10 C11 F11 -178.0(5) . . . . ?
F10 C10 C11 C12 -176.8(5) . . . . ?
C9 C10 C11 C12 2.5(8) . . . . ?
F11 C11 C12 F12 -0.7(9) . . . . ?
C10 C11 C12 F12 178.8(5) . . . . ?
F11 C11 C12 C13 179.9(5) . . . . ?
C10 C11 C12 C13 -0.7(9) . . . . ?
F12 C12 C13 F13 0.0(9) . . . . ?
C11 C12 C13 F13 179.4(5) . . . . ?
F12 C12 C13 C14 179.6(5) . . . . ?
C11 C12 C13 C14 -0.9(9) . . . . ?
F13 C13 C14 F14 0.0(8) . . . . ?
C12 C13 C14 F14 -179.7(5) . . . . ?
F13 C13 C14 C9 -179.6(5) . . . . ?
C12 C13 C14 C9 0.7(9) . . . . ?
C10 C9 C14 F14 -178.6(5) . . . . ?
C8 C9 C14 F14 3.5(8) . . . . ?
C10 C9 C14 C13 1.0(8) . . . . ?
C8 C9 C14 C13 -176.9(5) . . . . ?
C7 N2 C15 C16 -109.1(5) . . . . ?
C2 N2 C15 C16 61.1(6) . . . . ?
N2 C15 C16 C17 -134.7(5) . . . . ?
N2 C15 C16 C21 44.2(6) . . . . ?
C21 C16 C17 F17 177.9(5) . . . . ?
C15 C16 C17 F17 -3.2(7) . . . . ?
C21 C16 C17 C18 -2.7(8) . . . . ?
C15 C16 C17 C18 176.3(5) . . . . ?
F17 C17 C18 F18 0.3(8) . . . . ?
C16 C17 C18 F18 -179.1(5) . . . . ?
F17 C17 C18 C19 -179.3(5) . . . . ?
C16 C17 C18 C19 1.2(9) . . . . ?
F18 C18 C19 F19 1.0(9) . . . . ?
C17 C18 C19 F19 -179.4(5) . . . . ?
F18 C18 C19 C20 -178.4(5) . . . . ?
C17 C18 C19 C20 1.2(9) . . . . ?
F19 C19 C20 F20 0.0(8) . . . . ?
C18 C19 C20 F20 179.4(5) . . . . ?
F19 C19 C20 C21 178.5(5) . . . . ?
C18 C19 C20 C21 -2.1(8) . . . . ?
F20 C20 C21 F21 0.2(7) . . . . ?
C19 C20 C21 F21 -178.3(5) . . . . ?
F20 C20 C21 C16 179.0(5) . . . . ?
C19 C20 C21 C16 0.5(8) . . . . ?
C17 C16 C21 F21 -179.4(5) . . . . ?
C15 C16 C21 F21 1.6(8) . . . . ?
C17 C16 C21 C20 1.8(8) . . . . ?
C15 C16 C21 C20 -177.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A Br1 0.83(2) 2.44(3) 3.253(4) 168(8) 4_566
O1 H1B Br1 0.84(2) 2.50(4) 3.262(5) 150(7) .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.954
_refine_diff_density_rms         0.134

_iucr_refine_instructions_details 
;
TITL mm-om-1 in P 21/c
REM  transformed from space group : P21/a
CELL   0.71073 12.4829 16.1450 10.3729   90.000   91.529   90.000
ZERR   4        0.0003  0.0004  0.0002    0.000    0.001    0.000
LATT    1
SYMM   -X,1/2+Y,1/2-Z
SFAC  C    H    N    O    F    BR
UNIT  84   44   8    4    40   4
OMIT -3 50.05
OMIT 3 0 0
OMIT -1 1 2
OMIT 2 4 1
MERG   2
TEMP  -150
SIZE  0.25 0.18 0.14
EQIV $1 x, -y+1/2, z+1/2
HTAB O1 Br1_$1
HTAB O1 Br1
ACTA
CONF
HTAB
BOND $H
FMAP   2
PLAN   25
LIST   1
L.S.   10
WGHT    0.094200   10.928301
FVAR       0.41413
BR1   6    1.011020    0.308845    0.092023    11.00000    0.03578    0.03018 =
         0.03011   -0.00612    0.00214    0.00148
F10   5    0.838398    0.678634    0.167902    11.00000    0.02755    0.01547 =
         0.02648    0.00324   -0.00053   -0.00084
F11   5    0.677911    0.737689    0.017081    11.00000    0.03693    0.02681 =
         0.04233    0.01325    0.00011    0.01038
F12   5    0.550569    0.631943   -0.121427    11.00000    0.03651    0.05478 =
         0.04465    0.01039   -0.01952    0.00870
F13   5    0.590899    0.465655   -0.114089    11.00000    0.04335    0.04584 =
         0.04975   -0.00747   -0.02554   -0.00642
F14   5    0.757841    0.407419    0.028579    11.00000    0.03764    0.01936 =
         0.04055   -0.00736   -0.01118   -0.00050
F17   5    0.678362    0.252995    0.720414    11.00000    0.02376    0.04816 =
         0.02656    0.02008   -0.00216   -0.00144
F18   5    0.482508    0.291546    0.801246    11.00000    0.03575    0.07411 =
         0.03132    0.00552    0.01693   -0.00939
F19   5    0.349334    0.387190    0.651418    11.00000    0.01819    0.04948 =
         0.06557   -0.01755    0.01333    0.00290
F20   5    0.414036    0.439941    0.417194    11.00000    0.02072    0.03548 =
         0.06263    0.00642   -0.01148    0.01127
F21   5    0.611520    0.403831    0.337701    11.00000    0.02234    0.03448 =
         0.02783    0.01372   -0.00671    0.00379
N1    3    0.873818    0.473928    0.300054    11.00000    0.01361    0.01419 =
         0.01259   -0.00137    0.00119    0.00071
N2    3    0.818422    0.384194    0.439552    11.00000    0.01073    0.01020 =
         0.01751    0.00333   -0.00137   -0.00123
C1    1    0.871432    0.515069    0.418351    11.00000    0.01157    0.01603 =
         0.01696    0.00125   -0.00202    0.00322
C2    1    0.835944    0.457795    0.507142    11.00000    0.00708    0.01190 =
         0.01800   -0.00209   -0.00395    0.00243
C3    1    0.825472    0.477475    0.637482    11.00000    0.01343    0.01824 =
         0.01631    0.00094   -0.00132    0.00153
AFIX  43
H3    2    0.802155    0.438055    0.698673    11.00000    0.02139
AFIX   0
C4    1    0.851094    0.557573    0.671430    11.00000    0.01799    0.02441 =
         0.01721   -0.00604   -0.00254    0.00349
AFIX  43
H4    2    0.844529    0.573974    0.758819    11.00000    0.01862
AFIX   0
C5    1    0.886590    0.616031    0.581828    11.00000    0.02118    0.01285 =
         0.02531   -0.00483   -0.00794    0.00198
AFIX  43
H5    2    0.903535    0.670516    0.610310    11.00000    0.01518
AFIX   0
C6    1    0.897486    0.596145    0.452894    11.00000    0.01537    0.00894 =
         0.02576    0.00108    0.00032    0.00038
AFIX  43
H6    2    0.921281    0.635413    0.391749    11.00000    0.01652
AFIX   0
C7    1    0.842322    0.396140    0.316788    11.00000    0.01000    0.01358 =
         0.01655   -0.00103   -0.00220    0.00235
AFIX  43
H7    2    0.837595    0.355258    0.251013    11.00000   -1.20000
AFIX   0
C8    1    0.902920    0.509477    0.174094    11.00000    0.01654    0.01812 =
         0.01665    0.00168    0.00250   -0.00088
AFIX  23
H8A   2    0.938522    0.466417    0.122485    11.00000    0.03063
H8B   2    0.954535    0.555303    0.188638    11.00000    0.01752
AFIX   0
C9    1    0.805751    0.541842    0.099104    11.00000    0.01625    0.01949 =
         0.01401    0.00364    0.00305    0.00268
C10   1    0.780650    0.625230    0.095438    11.00000    0.01901    0.02003 =
         0.01512    0.00311    0.00459   -0.00135
C11   1    0.697544    0.655584    0.020732    11.00000    0.02710    0.02183 =
         0.02890    0.00891    0.00887    0.00758
C12   1    0.633433    0.602862   -0.049764    11.00000    0.02334    0.04569 =
         0.02802    0.01039   -0.00455    0.01022
C13   1    0.654179    0.518107   -0.045874    11.00000    0.02712    0.03652 =
         0.02584   -0.00182   -0.00529   -0.00804
C14   1    0.739318    0.489889    0.027150    11.00000    0.02390    0.02161 =
         0.02308   -0.00031   -0.00113    0.00059
C15   1    0.766510    0.309345    0.490895    11.00000    0.01218    0.00940 =
         0.02121    0.00268    0.00030   -0.00048
AFIX  23
H15A  2    0.807810    0.289093    0.567367    11.00000   -1.20000
H15B  2    0.765969    0.265129    0.424755    11.00000   -1.20000
AFIX   0
C16   1    0.653463    0.328355    0.527908    11.00000    0.01163    0.01423 =
         0.01861   -0.00379   -0.00119   -0.00135
C17   1    0.615367    0.300688    0.643295    11.00000    0.01643    0.02404 =
         0.02462   -0.00026   -0.00400   -0.00406
C18   1    0.514392    0.319800    0.686451    11.00000    0.02169    0.03466 =
         0.02702   -0.00743    0.01020   -0.01057
C19   1    0.447075    0.367165    0.611301    11.00000    0.01333    0.02995 =
         0.03850   -0.01402    0.00666   -0.00140
C20   1    0.480000    0.393949    0.492293    11.00000    0.01865    0.01584 =
         0.03914   -0.00348   -0.01038    0.00353
C21   1    0.582185    0.374764    0.452162    11.00000    0.01729    0.01587 =
         0.02200    0.00014   -0.00135   -0.00224
MOLE 2
O1    4    0.905347    0.185022    0.302147    11.00000    0.02856    0.03919 =
         0.02773   -0.00618   -0.00314   -0.00072
H1A   2    0.925989    0.180627    0.378246    11.00000   -1.50000
H1B   2    0.948856    0.200919    0.246572    11.00000   -1.50000
DFIX 0.84 O1 H1A O1 H1B
HKLF   4
 
REM  mm-om-1 in P 21/c
REM R1 =  0.0614 for   2990 Fo > 4sig(Fo)  and  0.0778 for all   3690 data
REM    328 parameters refined using      2 restraints
 
END
 
WGHT      0.0942     10.9375
REM Highest difference peak  0.691,  deepest hole -0.954,  1-sigma level  0.134
Q1    1   0.8098  0.4191  0.7502  11.00000  0.05    0.69
Q2    1   0.8036  0.3425  0.4706  11.00000  0.05    0.58
Q3    1   0.8034  0.6519  0.1473  11.00000  0.05    0.58
Q4    1   0.6824  0.6978  0.0249  11.00000  0.05    0.56
Q5    1   0.6469  0.5605 -0.0409  11.00000  0.05    0.55
Q6    1   0.8234  0.4171  0.4734  11.00000  0.05    0.54
Q7    1   0.7955  0.5830  0.1059  11.00000  0.05    0.53
Q8    1   0.8857  0.4906  0.2400  11.00000  0.05    0.53
Q9    1   0.4555  0.4204  0.4462  11.00000  0.05    0.52
Q10   1   0.7488  0.4566  0.0250  11.00000  0.05    0.51
Q11   1   0.8864  0.6065  0.5097  11.00000  0.05    0.50
Q12   1   0.8372  0.3841  0.4141  11.00000  0.05    0.50
Q13   1   0.6400  0.3234  0.5639  11.00000  0.05    0.49
Q14   1   0.8149  0.6959  0.1835  11.00000  0.05    0.49
Q15   1   0.7353  0.6384  0.0685  11.00000  0.05    0.48
Q16   1   0.8529  0.4995  0.4612  11.00000  0.05    0.48
Q17   1   0.8678  0.4992  0.3476  11.00000  0.05    0.47
Q18   1   0.5997  0.4178  0.3124  11.00000  0.05    0.47
Q19   1   0.8447  0.6977  0.1462  11.00000  0.05    0.47
Q20   1   0.6029  0.3912  0.3989  11.00000  0.05    0.45
Q21   1   0.6576  0.6269  0.0013  11.00000  0.05    0.45
Q22   1   0.4333  0.4459  0.3573  11.00000  0.05    0.45
Q23   1   0.8859  0.5539  0.4353  11.00000  0.05    0.44
Q24   1   0.6862  0.5142  0.0175  11.00000  0.05    0.44
Q25   1   0.6216  0.3436  0.4817  11.00000  0.05    0.44
;
_database_code_depnum_ccdc_archive 'CCDC 1005283'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-088

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H11 F5 N, Br '
_chemical_formula_sum            'C14 H11 Br F5 N'
_chemical_formula_weight         368.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.7503(2)
_cell_length_b                   25.0706(9)
_cell_length_c                   9.5048(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.871(2)
_cell_angle_gamma                90.00
_cell_volume                     1365.30(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3273
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.407

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    3.060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5525
_exptl_absorpt_correction_T_max  0.7103
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14953
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_av_sigmaI/netI    0.0594
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2389
_reflns_number_gt                1812
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2006)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1569P)^2^+12.1369P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2389
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0884
_refine_ls_wR_factor_ref         0.2581
_refine_ls_wR_factor_gt          0.2410
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.67473(14) 0.25277(3) 0.11692(9) 0.0200(4) Uani 1 1 d . . .
F10 F 0.4142(9) 0.3637(2) 0.1114(7) 0.0296(14) Uani 1 1 d . . .
F11 F 0.2629(10) 0.4505(2) 0.2424(6) 0.0329(15) Uani 1 1 d . . .
F12 F -0.1653(10) 0.4919(2) 0.1601(6) 0.0301(14) Uani 1 1 d . . .
F13 F -0.4308(9) 0.4479(2) -0.0609(6) 0.0309(14) Uani 1 1 d . . .
F14 F -0.2794(9) 0.3616(2) -0.1908(7) 0.0317(14) Uani 1 1 d . . .
N1 N 0.1525(14) 0.2607(3) -0.0447(8) 0.0177(17) Uani 1 1 d . . .
H1C H 0.0095 0.2579 -0.0086 0.021 Uiso 1 1 calc R . .
H1D H 0.2653 0.2610 0.0300 0.021 Uiso 1 1 calc R . .
C1 C 0.1889(16) 0.2129(4) -0.1354(10) 0.021(2) Uani 1 1 d . . .
H1A H 0.3549 0.2111 -0.1554 0.025 Uiso 1 1 calc R . .
H1B H 0.0934 0.2168 -0.2265 0.025 Uiso 1 1 calc R . .
C2 C 0.1228(16) 0.1619(4) -0.0646(9) 0.020(2) Uani 1 1 d . . .
C3 C 0.2740(18) 0.1372(4) 0.0379(10) 0.023(2) Uani 1 1 d . . .
H3 H 0.4226 0.1524 0.0644 0.028 Uiso 1 1 calc R . .
C4 C 0.2065(19) 0.0902(4) 0.1017(11) 0.028(2) Uani 1 1 d . . .
H4 H 0.3094 0.0736 0.1721 0.033 Uiso 1 1 calc R . .
C5 C -0.0100(19) 0.0674(4) 0.0631(10) 0.025(2) Uani 1 1 d . . .
H5 H -0.0546 0.0351 0.1059 0.030 Uiso 1 1 calc R . .
C6 C -0.1602(17) 0.0922(4) -0.0385(12) 0.028(2) Uani 1 1 d . . .
H6 H -0.3093 0.0771 -0.0646 0.033 Uiso 1 1 calc R . .
C7 C -0.0924(18) 0.1393(4) -0.1027(12) 0.026(2) Uani 1 1 d . . .
H7 H -0.1953 0.1558 -0.1730 0.031 Uiso 1 1 calc R . .
C8 C 0.1627(16) 0.3119(4) -0.1241(9) 0.019(2) Uani 1 1 d . . .
H8A H 0.0685 0.3083 -0.2157 0.023 Uiso 1 1 calc R . .
H8B H 0.3262 0.3188 -0.1440 0.023 Uiso 1 1 calc R . .
C9 C 0.0743(16) 0.3589(3) -0.0453(10) 0.018(2) Uani 1 1 d . . .
C10 C 0.2011(16) 0.3833(4) 0.0667(11) 0.021(2) Uani 1 1 d . . .
C11 C 0.1276(17) 0.4279(4) 0.1372(10) 0.021(2) Uani 1 1 d . . .
C12 C -0.0883(16) 0.4491(3) 0.0942(10) 0.021(2) Uani 1 1 d . . .
C13 C -0.2213(16) 0.4271(4) -0.0192(10) 0.022(2) Uani 1 1 d . . .
C14 C -0.1434(17) 0.3822(4) -0.0837(10) 0.023(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0145(6) 0.0266(6) 0.0190(6) -0.0014(4) 0.0011(4) 0.0016(3)
F10 0.020(3) 0.031(3) 0.037(4) 0.002(3) -0.002(2) 0.004(2)
F11 0.034(3) 0.029(3) 0.033(4) -0.001(3) -0.010(3) -0.004(2)
F12 0.034(3) 0.027(3) 0.029(3) -0.001(2) 0.005(3) 0.008(2)
F13 0.022(3) 0.033(3) 0.038(4) 0.002(3) 0.000(3) 0.006(2)
F14 0.022(3) 0.035(3) 0.037(4) -0.004(3) -0.005(3) -0.002(2)
N1 0.021(4) 0.017(4) 0.015(4) -0.003(3) -0.005(3) -0.006(3)
C1 0.027(5) 0.019(5) 0.016(5) -0.004(4) 0.007(4) 0.010(4)
C2 0.022(5) 0.029(5) 0.009(4) -0.005(4) 0.003(4) 0.003(4)
C3 0.030(5) 0.028(5) 0.012(5) -0.005(4) 0.002(4) 0.000(4)
C4 0.040(6) 0.022(5) 0.021(6) 0.004(4) 0.001(5) 0.000(4)
C5 0.044(6) 0.019(5) 0.013(5) -0.001(4) 0.008(4) 0.003(4)
C6 0.020(5) 0.026(5) 0.038(7) -0.005(4) 0.011(4) -0.005(4)
C7 0.024(5) 0.022(5) 0.032(6) -0.010(4) -0.001(4) 0.008(4)
C8 0.028(5) 0.022(5) 0.006(4) 0.000(3) 0.007(4) -0.002(4)
C9 0.024(5) 0.016(4) 0.017(5) 0.004(4) 0.014(4) -0.003(4)
C10 0.019(5) 0.020(5) 0.025(5) 0.001(4) 0.004(4) 0.004(4)
C11 0.029(5) 0.021(5) 0.014(5) 0.006(4) 0.002(4) -0.007(4)
C12 0.025(5) 0.014(4) 0.026(5) -0.006(4) 0.011(4) 0.001(4)
C13 0.023(5) 0.022(5) 0.021(5) 0.004(4) 0.005(4) 0.001(4)
C14 0.029(5) 0.020(5) 0.019(5) 0.004(4) -0.001(4) -0.007(4)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F10 C10 1.355(10) . ?
F11 C11 1.339(11) . ?
F12 C12 1.338(10) . ?
F13 C13 1.342(11) . ?
F14 C14 1.334(11) . ?
N1 C8 1.493(11) . ?
N1 C1 1.500(11) . ?
N1 H1C 0.9200 . ?
N1 H1D 0.9200 . ?
C1 C2 1.509(14) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C7 1.381(14) . ?
C2 C3 1.394(13) . ?
C3 C4 1.396(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.400(15) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.507(12) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.382(14) . ?
C9 C14 1.402(14) . ?
C10 C11 1.387(14) . ?
C11 C12 1.380(13) . ?
C12 C13 1.382(13) . ?
C13 C14 1.374(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 112.5(7) . . ?
C8 N1 H1C 109.1 . . ?
C1 N1 H1C 109.1 . . ?
C8 N1 H1D 109.1 . . ?
C1 N1 H1D 109.1 . . ?
H1C N1 H1D 107.8 . . ?
N1 C1 C2 111.6(7) . . ?
N1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C7 C2 C3 119.5(9) . . ?
C7 C2 C1 119.0(9) . . ?
C3 C2 C1 121.4(8) . . ?
C2 C3 C4 119.9(9) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.6(9) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 119.3(9) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 120.1(9) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 120.6(10) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
N1 C8 C9 113.1(7) . . ?
N1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C14 114.6(8) . . ?
C10 C9 C8 123.4(8) . . ?
C14 C9 C8 121.9(8) . . ?
F10 C10 C9 119.0(8) . . ?
F10 C10 C11 116.4(8) . . ?
C9 C10 C11 124.5(8) . . ?
F11 C11 C12 120.6(9) . . ?
F11 C11 C10 121.3(9) . . ?
C12 C11 C10 118.0(9) . . ?
F12 C12 C11 119.7(8) . . ?
F12 C12 C13 120.2(8) . . ?
C11 C12 C13 120.1(8) . . ?
F13 C13 C14 120.4(9) . . ?
F13 C13 C12 119.9(8) . . ?
C14 C13 C12 119.7(9) . . ?
F14 C14 C13 117.7(9) . . ?
F14 C14 C9 119.3(8) . . ?
C13 C14 C9 122.9(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 -166.6(7) . . . . ?
N1 C1 C2 C7 99.5(10) . . . . ?
N1 C1 C2 C3 -80.5(10) . . . . ?
C7 C2 C3 C4 -0.3(14) . . . . ?
C1 C2 C3 C4 179.7(8) . . . . ?
C2 C3 C4 C5 0.5(15) . . . . ?
C3 C4 C5 C6 -0.8(15) . . . . ?
C4 C5 C6 C7 0.9(15) . . . . ?
C3 C2 C7 C6 0.4(14) . . . . ?
C1 C2 C7 C6 -179.5(9) . . . . ?
C5 C6 C7 C2 -0.7(15) . . . . ?
C1 N1 C8 C9 167.1(7) . . . . ?
N1 C8 C9 C10 76.2(11) . . . . ?
N1 C8 C9 C14 -105.7(10) . . . . ?
C14 C9 C10 F10 -179.9(8) . . . . ?
C8 C9 C10 F10 -1.6(14) . . . . ?
C14 C9 C10 C11 -0.9(14) . . . . ?
C8 C9 C10 C11 177.3(9) . . . . ?
F10 C10 C11 F11 1.0(13) . . . . ?
C9 C10 C11 F11 -178.0(8) . . . . ?
F10 C10 C11 C12 179.9(8) . . . . ?
C9 C10 C11 C12 0.9(15) . . . . ?
F11 C11 C12 F12 -1.3(14) . . . . ?
C10 C11 C12 F12 179.8(8) . . . . ?
F11 C11 C12 C13 176.6(8) . . . . ?
C10 C11 C12 C13 -2.2(14) . . . . ?
F12 C12 C13 F13 -1.8(14) . . . . ?
C11 C12 C13 F13 -179.7(8) . . . . ?
F12 C12 C13 C14 -178.3(8) . . . . ?
C11 C12 C13 C14 3.7(14) . . . . ?
F13 C13 C14 F14 2.0(13) . . . . ?
C12 C13 C14 F14 178.5(8) . . . . ?
F13 C13 C14 C9 179.6(8) . . . . ?
C12 C13 C14 C9 -3.9(14) . . . . ?
C10 C9 C14 F14 180.0(8) . . . . ?
C8 C9 C14 F14 1.7(13) . . . . ?
C10 C9 C14 C13 2.4(13) . . . . ?
C8 C9 C14 C13 -175.8(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         4.386
_refine_diff_density_min         -0.835
_refine_diff_density_rms         0.288

_iucr_refine_instructions_details 
;
TITL mm-088 in P 21/c
CELL  0.71073   5.7503  25.0706   9.5048   90.000   94.871   90.000
ZERR     4.00   0.0002   0.0009   0.0004    0.000    0.002    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    F    BR
UNIT  56   44   4    20   4
MERG   2
SHEL 0.8 99
OMIT    -3.00  50.05
OMIT     1   7   3
OMIT     0   2   0
OMIT     2  11   1
OMIT     0   6   5
OMIT     2   3   1
OMIT     0   1   5
OMIT     1   1   3
OMIT     1   2   3
OMIT     1  23   3
OMIT     0  16   5
OMIT     1  20   3
OMIT  -1   4   2
OMIT 2  10   1
OMIT 2   3   6
OMIT 1   6   3
OMIT -1  12   7
OMIT -1   2   7
OMIT 1  25   3
OMIT -1   6   8
OMIT -1  11   7
FMAP   2
PLAN   25
SIZE     0.12   0.14   0.22
ACTA
BOND   $H
CONF
L.S.  10
TEMP  -150.00
WGHT    0.156900   12.136900
FVAR       0.29984
BR1   5    0.674725    0.252767    0.116915    11.00000    0.01450    0.02657 =
         0.01896   -0.00142    0.00115    0.00160
F10   4    0.414192    0.363722    0.111445    11.00000    0.01993    0.03114 =
         0.03699    0.00223   -0.00210    0.00372
F11   4    0.262899    0.450482    0.242402    11.00000    0.03386    0.02945 =
         0.03325   -0.00066   -0.01001   -0.00375
F12   4   -0.165287    0.491936    0.160147    11.00000    0.03419    0.02710 =
         0.02929   -0.00059    0.00477    0.00824
F13   4   -0.430781    0.447944   -0.060903    11.00000    0.02167    0.03273 =
         0.03765    0.00192   -0.00035    0.00576
F14   4   -0.279388    0.361625   -0.190761    11.00000    0.02156    0.03508 =
         0.03727   -0.00448   -0.00515   -0.00214
N1    3    0.152548    0.260675   -0.044671    11.00000    0.02068    0.01656 =
         0.01458   -0.00320   -0.00512   -0.00573
AFIX  23
H1C   2    0.009550    0.257935   -0.008586    11.00000   -1.20000
H1D   2    0.265275    0.261003    0.030045    11.00000   -1.20000
AFIX   0
C1    1    0.188911    0.212911   -0.135357    11.00000    0.02721    0.01921 =
         0.01626   -0.00364    0.00700    0.00972
AFIX  23
H1A   2    0.354882    0.211116   -0.155411    11.00000   -1.20000
H1B   2    0.093399    0.216767   -0.226465    11.00000   -1.20000
AFIX   0
C2    1    0.122835    0.161874   -0.064621    11.00000    0.02171    0.02933 =
         0.00906   -0.00479    0.00316    0.00307
C3    1    0.273972    0.137242    0.037929    11.00000    0.03019    0.02835 =
         0.01184   -0.00469    0.00168    0.00014
AFIX  43
H3    2    0.422608    0.152443    0.064385    11.00000   -1.20000
AFIX   0
C4    1    0.206515    0.090177    0.101712    11.00000    0.04003    0.02156 =
         0.02123    0.00394    0.00144    0.00031
AFIX  43
H4    2    0.309389    0.073609    0.172069    11.00000   -1.20000
AFIX   0
C5    1   -0.010011    0.067351    0.063112    11.00000    0.04384    0.01944 =
         0.01321   -0.00120    0.00752    0.00275
AFIX  43
H5    2   -0.054569    0.035101    0.105908    11.00000   -1.20000
AFIX   0
C6    1   -0.160188    0.092155   -0.038498    11.00000    0.02029    0.02645 =
         0.03767   -0.00542    0.01057   -0.00468
AFIX  43
H6    2   -0.309328    0.077144   -0.064596    11.00000   -1.20000
AFIX   0
C7    1   -0.092413    0.139260   -0.102654    11.00000    0.02378    0.02192 =
         0.03214   -0.00970   -0.00089    0.00800
AFIX  43
H7    2   -0.195349    0.155828   -0.172979    11.00000   -1.20000
AFIX   0
C8    1    0.162702    0.311903   -0.124050    11.00000    0.02842    0.02239 =
         0.00649    0.00035    0.00724   -0.00240
AFIX  23
H8A   2    0.068491    0.308338   -0.215695    11.00000   -1.20000
H8B   2    0.326234    0.318780   -0.143974    11.00000   -1.20000
AFIX   0
C9    1    0.074266    0.358887   -0.045329    11.00000    0.02393    0.01643 =
         0.01721    0.00387    0.01421   -0.00346
C10   1    0.201123    0.383336    0.066651    11.00000    0.01891    0.02020 =
         0.02470    0.00139    0.00412    0.00423
C11   1    0.127602    0.427900    0.137220    11.00000    0.02934    0.02076 =
         0.01358    0.00573    0.00221   -0.00675
C12   1   -0.088343    0.449054    0.094244    11.00000    0.02499    0.01419 =
         0.02610   -0.00617    0.01125    0.00054
C13   1   -0.221252    0.427073   -0.019183    11.00000    0.02284    0.02176 =
         0.02085    0.00447    0.00451    0.00149
C14   1   -0.143383    0.382239   -0.083742    11.00000    0.02929    0.02023 =
         0.01879    0.00377   -0.00075   -0.00729
HKLF    4
 
REM  mm-088 in P 21/c
REM R1 =  0.0884 for   1812 Fo > 4sig(Fo)  and  0.1119 for all   2389 data
REM    190 parameters refined using      0 restraints
 
END
 
WGHT      0.1569     12.1494
REM Highest difference peak  4.386,  deepest hole -0.835,  1-sigma level  0.288
Q1    1   0.8770  0.2496  0.2172  11.00000  0.05    4.39
Q2    1   0.4735  0.2496  0.0201  11.00000  0.05    4.10
Q3    1   0.0699  0.2497 -0.1812  11.00000  0.05    3.93
Q4    1   0.2832  0.2498 -0.0796  11.00000  0.05    3.87
Q5    1   0.3202  0.0654  0.2430  11.00000  0.05    0.87
Q6    1   0.1818  0.0522  0.2159  11.00000  0.05    0.81
Q7    1   0.5301  0.3684  0.1637  11.00000  0.05    0.80
Q8    1  -0.1651  0.1404 -0.1620  11.00000  0.05    0.80
Q9    1  -0.4150  0.3600 -0.2774  11.00000  0.05    0.77
Q10   1  -0.2229  0.0546  0.0179  11.00000  0.05    0.76
Q11   1   0.3900  0.4509  0.3220  11.00000  0.05    0.75
Q12   1   0.4088  0.2575  0.1255  11.00000  0.05    0.75
Q13   1   0.3350  0.1371  0.0948  11.00000  0.05    0.68
Q14   1   0.1225  0.3620  0.0087  11.00000  0.05    0.66
Q15   1   0.6619  0.2939  0.1023  11.00000  0.05    0.65
Q16   1  -0.5720  0.4430 -0.1547  11.00000  0.05    0.65
Q17   1  -0.1558  0.4394  0.0376  11.00000  0.05    0.63
Q18   1   0.0150  0.4432  0.1230  11.00000  0.05    0.63
Q19   1  -0.4939  0.0678 -0.1723  11.00000  0.05    0.62
Q20   1  -0.0059  0.3629 -0.0580  11.00000  0.05    0.62
Q21   1   0.5786  0.3648  0.2164  11.00000  0.05    0.61
Q22   1   0.5071  0.1410  0.1456  11.00000  0.05    0.60
Q23   1   0.6731  0.1469  0.1193  11.00000  0.05    0.59
Q24   1   0.1792  0.1408  0.0345  11.00000  0.05    0.58
Q25   1  -0.1565  0.3571 -0.1754  11.00000  0.05    0.57
;

# start Validation Reply Form
_vrf_DIFMX01_mm-088              
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00
RESPONSE: See the last response.
;
_vrf_PLAT094_mm-088              
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       5.25 Why ? 
RESPONSE: See the last response.
;
_vrf_PLAT097_mm-088              
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       4.39 eA-3  
RESPONSE: See the last response.
;
_vrf_PLAT930_mm-088              
;
PROBLEM: Check Twin Law ( 1 0 -2)[ 4 0 -3] Estimated BASF       0.33       
RESPONSE: All these four B alerts are the result of systematic errors or
problems in the data. The twinning which is occurring is most probably 
pseudo-type twinning and we could not solve it. We tried the refinements
with suspected twin law and also with HKLF5 method, but they did not give
any better result. Platon/Twinrotmat gives the same twin law, but it seems
that it is not the correct one. The large residual densities are the 
elctron densities of the second domain, which we were not able to determine. 
;
# end Validation Reply Form
_database_code_depnum_ccdc_archive 'CCDC 1005284'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-cb-42-2b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 F10 N2, C H4 O, 2(Br)'
_chemical_formula_sum            'C21 H24 Br2 F10 N2 O'
_chemical_formula_weight         670.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.2107(3)
_cell_length_b                   7.19550(10)
_cell_length_c                   25.9512(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.1490(10)
_cell_angle_gamma                90.00
_cell_volume                     2466.36(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6555
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.805
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    3.380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5234
_exptl_absorpt_correction_T_max  0.8766
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15646
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         25.25
_reflns_number_total             4457
_reflns_number_gt                3527
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0130P)^2^+1.2082P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4457
_refine_ls_number_parameters     328
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0650
_refine_ls_wR_factor_gt          0.0608
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.47437(3) 0.69521(4) 0.697216(13) 0.02042(9) Uani 1 1 d . . .
Br2 Br 0.26693(3) 0.12325(4) 0.512164(13) 0.02292(10) Uani 1 1 d . . .
F5 F 0.54239(14) 0.2861(2) 0.48470(7) 0.0237(4) Uani 1 1 d . . .
F6 F 0.69860(15) 0.3096(2) 0.41999(7) 0.0294(5) Uani 1 1 d . . .
F7 F 0.88315(15) 0.4215(3) 0.45539(8) 0.0364(5) Uani 1 1 d . . .
F8 F 0.90895(14) 0.5239(3) 0.55591(8) 0.0404(6) Uani 1 1 d . . .
F9 F 0.75242(15) 0.5006(3) 0.62058(7) 0.0329(5) Uani 1 1 d . . .
F12 F 0.22930(14) -0.0622(2) 0.77058(7) 0.0219(4) Uani 1 1 d . . .
F13 F 0.06266(14) -0.0865(2) 0.82838(7) 0.0276(5) Uani 1 1 d . . .
F14 F -0.04886(13) 0.2218(3) 0.84764(7) 0.0278(5) Uani 1 1 d . . .
F15 F 0.00392(14) 0.5526(2) 0.80602(7) 0.0264(5) Uani 1 1 d . . .
F16 F 0.16697(14) 0.5778(2) 0.74609(7) 0.0237(5) Uani 1 1 d . . .
N1 N 0.54901(18) 0.1821(3) 0.61921(9) 0.0135(6) Uani 1 1 d . . .
N2 N 0.27736(18) 0.2263(3) 0.66648(9) 0.0132(6) Uani 1 1 d . . .
C1 C 0.4674(2) 0.1986(4) 0.65954(11) 0.0133(7) Uani 1 1 d . . .
H1A H 0.4923 0.2788 0.6881 0.016 Uiso 1 1 calc R . .
H1B H 0.4531 0.0741 0.6739 0.016 Uiso 1 1 calc R . .
C2 C 0.3699(2) 0.2806(4) 0.63676(11) 0.0135(7) Uani 1 1 d . . .
H2A H 0.3756 0.4177 0.6363 0.016 Uiso 1 1 calc R . .
H2B H 0.3614 0.2380 0.6007 0.016 Uiso 1 1 calc R . .
C3 C 0.5586(2) 0.3698(4) 0.59201(12) 0.0161(7) Uani 1 1 d . . .
H3A H 0.4947 0.3954 0.5727 0.019 Uiso 1 1 calc R . .
H3B H 0.5672 0.4681 0.6184 0.019 Uiso 1 1 calc R . .
C4 C 0.6453(2) 0.3808(4) 0.55539(12) 0.0146(7) Uani 1 1 d . . .
C5 C 0.6338(2) 0.3388(4) 0.50361(12) 0.0156(7) Uani 1 1 d . . .
C6 C 0.7128(3) 0.3513(4) 0.47016(12) 0.0185(7) Uani 1 1 d . . .
C7 C 0.8056(2) 0.4090(4) 0.48797(13) 0.0216(8) Uani 1 1 d . . .
C8 C 0.8198(2) 0.4583(4) 0.53899(14) 0.0236(8) Uani 1 1 d . . .
C9 C 0.7389(3) 0.4442(4) 0.57137(12) 0.0211(8) Uani 1 1 d . . .
C10 C 0.2956(2) 0.2725(4) 0.72337(11) 0.0155(7) Uani 1 1 d . . .
H10A H 0.3480 0.1875 0.7376 0.019 Uiso 1 1 calc R . .
H10B H 0.3223 0.4008 0.7261 0.019 Uiso 1 1 calc R . .
C11 C 0.2029(2) 0.2575(4) 0.75536(11) 0.0136(7) Uani 1 1 d . . .
C12 C 0.1744(2) 0.0924(4) 0.77834(11) 0.0147(7) Uani 1 1 d . . .
C13 C 0.0905(2) 0.0778(4) 0.80854(12) 0.0190(7) Uani 1 1 d . . .
C14 C 0.0328(2) 0.2340(4) 0.81816(12) 0.0194(7) Uani 1 1 d . . .
C15 C 0.0601(2) 0.4008(4) 0.79699(12) 0.0187(7) Uani 1 1 d . . .
C16 C 0.1431(2) 0.4108(4) 0.76624(12) 0.0160(7) Uani 1 1 d . . .
C17 C 0.6448(2) 0.1318(4) 0.64822(12) 0.0189(7) Uani 1 1 d . . .
H17A H 0.6621 0.2310 0.6727 0.028 Uiso 1 1 calc R . .
H17B H 0.7000 0.1166 0.6239 0.028 Uiso 1 1 calc R . .
H17C H 0.6348 0.0152 0.6669 0.028 Uiso 1 1 calc R . .
C18 C 0.5240(2) 0.0288(4) 0.58174(12) 0.0180(7) Uani 1 1 d . . .
H18A H 0.4616 0.0598 0.5626 0.027 Uiso 1 1 calc R . .
H18B H 0.5145 -0.0877 0.6006 0.027 Uiso 1 1 calc R . .
H18C H 0.5796 0.0144 0.5576 0.027 Uiso 1 1 calc R . .
C19 C 0.2535(2) 0.0235(4) 0.65805(12) 0.0173(7) Uani 1 1 d . . .
H19A H 0.1937 -0.0103 0.6777 0.026 Uiso 1 1 calc R . .
H19B H 0.3113 -0.0521 0.6697 0.026 Uiso 1 1 calc R . .
H19C H 0.2400 0.0012 0.6213 0.026 Uiso 1 1 calc R . .
C20 C 0.1909(2) 0.3390(4) 0.64392(12) 0.0182(7) Uani 1 1 d . . .
H20A H 0.2045 0.4715 0.6492 0.027 Uiso 1 1 calc R . .
H20B H 0.1280 0.3051 0.6610 0.027 Uiso 1 1 calc R . .
H20C H 0.1841 0.3134 0.6069 0.027 Uiso 1 1 calc R . .
O21 O 0.1322(2) 0.5037(4) 0.90886(10) 0.0413(7) Uani 1 1 d D . .
H21 H 0.174(3) 0.453(5) 0.9319(13) 0.062 Uiso 1 1 d D . .
C21 C 0.0392(3) 0.5552(6) 0.93115(15) 0.0410(10) Uani 1 1 d . . .
H21A H 0.0523 0.6070 0.9656 0.061 Uiso 1 1 calc R . .
H21B H -0.0043 0.4456 0.9339 0.061 Uiso 1 1 calc R . .
H21C H 0.0054 0.6488 0.9094 0.061 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0267(2) 0.01528(17) 0.01907(18) -0.00025(14) -0.00374(14) -0.00057(14)
Br2 0.0277(2) 0.02173(18) 0.01913(18) -0.00184(15) -0.00331(15) 0.00366(15)
F5 0.0248(11) 0.0267(10) 0.0195(10) -0.0010(8) -0.0045(9) -0.0090(9)
F6 0.0453(14) 0.0277(10) 0.0156(10) -0.0002(9) 0.0073(9) 0.0009(9)
F7 0.0274(12) 0.0484(13) 0.0342(13) 0.0145(10) 0.0190(10) 0.0078(10)
F8 0.0174(12) 0.0629(14) 0.0406(14) 0.0131(11) -0.0025(10) -0.0165(10)
F9 0.0291(12) 0.0479(13) 0.0215(11) -0.0037(10) -0.0028(9) -0.0177(10)
F12 0.0273(11) 0.0165(9) 0.0221(10) 0.0020(8) 0.0042(9) 0.0050(8)
F13 0.0318(12) 0.0249(11) 0.0265(11) 0.0052(9) 0.0076(9) -0.0092(9)
F14 0.0182(11) 0.0398(11) 0.0257(11) -0.0021(9) 0.0102(9) -0.0049(9)
F15 0.0263(12) 0.0278(10) 0.0252(11) -0.0035(9) 0.0044(9) 0.0114(9)
F16 0.0331(12) 0.0140(9) 0.0241(11) 0.0021(8) 0.0068(9) 0.0022(8)
N1 0.0146(14) 0.0135(13) 0.0127(14) 0.0010(11) 0.0030(11) -0.0003(11)
N2 0.0107(14) 0.0137(13) 0.0153(14) -0.0010(11) 0.0026(11) -0.0016(11)
C1 0.0134(17) 0.0163(16) 0.0102(16) -0.0002(13) 0.0060(13) -0.0005(13)
C2 0.0164(17) 0.0114(15) 0.0129(16) 0.0002(13) 0.0040(14) -0.0005(13)
C3 0.0191(18) 0.0124(15) 0.0169(17) 0.0008(13) 0.0031(14) -0.0010(13)
C4 0.0169(18) 0.0134(15) 0.0137(17) -0.0005(13) 0.0016(14) -0.0011(13)
C5 0.0171(18) 0.0095(15) 0.0199(18) 0.0003(13) -0.0034(15) -0.0007(13)
C6 0.030(2) 0.0130(16) 0.0130(17) 0.0022(13) 0.0028(15) 0.0011(14)
C7 0.0148(19) 0.0256(19) 0.0247(19) 0.0104(15) 0.0102(16) 0.0041(14)
C8 0.0116(18) 0.0277(19) 0.031(2) 0.0107(16) -0.0031(16) -0.0037(15)
C9 0.025(2) 0.0243(18) 0.0141(17) -0.0016(15) 0.0028(15) -0.0070(15)
C10 0.0178(18) 0.0157(16) 0.0131(16) -0.0008(13) 0.0013(14) -0.0008(13)
C11 0.0139(17) 0.0175(16) 0.0094(16) -0.0011(13) -0.0009(13) -0.0025(13)
C12 0.0158(18) 0.0167(17) 0.0114(16) -0.0011(13) -0.0029(14) 0.0033(13)
C13 0.0217(19) 0.0199(18) 0.0153(18) 0.0038(14) -0.0033(15) -0.0060(14)
C14 0.0162(18) 0.0291(19) 0.0129(17) -0.0018(14) 0.0039(15) -0.0024(15)
C15 0.0199(19) 0.0205(18) 0.0155(17) -0.0065(14) -0.0012(14) 0.0071(14)
C16 0.0186(18) 0.0161(17) 0.0132(17) 0.0007(13) -0.0014(14) -0.0029(13)
C17 0.0126(17) 0.0223(17) 0.0216(18) 0.0045(15) -0.0013(14) 0.0047(14)
C18 0.0226(19) 0.0152(16) 0.0163(17) -0.0050(14) 0.0006(15) -0.0015(14)
C19 0.0209(19) 0.0121(15) 0.0189(18) -0.0032(14) 0.0028(15) -0.0035(13)
C20 0.0136(18) 0.0240(18) 0.0169(17) 0.0031(14) 0.0005(14) 0.0053(14)
O21 0.0331(17) 0.0666(19) 0.0242(15) 0.0120(14) -0.0003(12) 0.0038(14)
C21 0.039(3) 0.060(3) 0.024(2) 0.000(2) -0.0036(19) -0.004(2)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F5 C5 1.348(3) . ?
F6 C6 1.346(4) . ?
F7 C7 1.344(3) . ?
F8 C8 1.334(4) . ?
F9 C9 1.348(4) . ?
F12 C12 1.346(3) . ?
F13 C13 1.344(3) . ?
F14 C14 1.337(3) . ?
F15 C15 1.344(3) . ?
F16 C16 1.351(3) . ?
N1 C18 1.503(4) . ?
N1 C17 1.504(4) . ?
N1 C1 1.523(3) . ?
N1 C3 1.530(4) . ?
N2 C19 1.508(3) . ?
N2 C20 1.509(4) . ?
N2 C2 1.510(3) . ?
N2 C10 1.528(4) . ?
C1 C2 1.524(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.505(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C9 1.375(4) . ?
C4 C5 1.383(4) . ?
C5 C6 1.374(4) . ?
C6 C7 1.366(5) . ?
C7 C8 1.380(5) . ?
C8 C9 1.376(4) . ?
C10 C11 1.497(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.385(4) . ?
C11 C16 1.389(4) . ?
C12 C13 1.374(4) . ?
C13 C14 1.384(4) . ?
C14 C15 1.372(4) . ?
C15 C16 1.371(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O21 C21 1.418(4) . ?
O21 H21 0.883(19) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 N1 C17 108.6(2) . . ?
C18 N1 C1 110.6(2) . . ?
C17 N1 C1 106.0(2) . . ?
C18 N1 C3 111.6(2) . . ?
C17 N1 C3 111.5(2) . . ?
C1 N1 C3 108.3(2) . . ?
C19 N2 C20 108.0(2) . . ?
C19 N2 C2 110.2(2) . . ?
C20 N2 C2 106.1(2) . . ?
C19 N2 C10 112.3(2) . . ?
C20 N2 C10 111.2(2) . . ?
C2 N2 C10 108.9(2) . . ?
N1 C1 C2 111.6(2) . . ?
N1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
N2 C2 C1 112.8(2) . . ?
N2 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
N2 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 N1 114.1(2) . . ?
C4 C3 H3A 108.7 . . ?
N1 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
N1 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C9 C4 C5 116.5(3) . . ?
C9 C4 C3 121.3(3) . . ?
C5 C4 C3 122.1(3) . . ?
F5 C5 C6 118.3(3) . . ?
F5 C5 C4 119.7(3) . . ?
C6 C5 C4 122.0(3) . . ?
F6 C6 C7 120.1(3) . . ?
F6 C6 C5 120.2(3) . . ?
C7 C6 C5 119.6(3) . . ?
F7 C7 C6 119.8(3) . . ?
F7 C7 C8 119.7(3) . . ?
C6 C7 C8 120.4(3) . . ?
F8 C8 C9 121.1(3) . . ?
F8 C8 C7 120.6(3) . . ?
C9 C8 C7 118.3(3) . . ?
F9 C9 C4 119.1(3) . . ?
F9 C9 C8 117.8(3) . . ?
C4 C9 C8 123.0(3) . . ?
C11 C10 N2 113.9(2) . . ?
C11 C10 H10A 108.8 . . ?
N2 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
N2 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C16 115.6(3) . . ?
C12 C11 C10 122.2(3) . . ?
C16 C11 C10 122.0(3) . . ?
F12 C12 C13 117.7(3) . . ?
F12 C12 C11 119.5(3) . . ?
C13 C12 C11 122.7(3) . . ?
F13 C13 C12 121.1(3) . . ?
F13 C13 C14 119.3(3) . . ?
C12 C13 C14 119.6(3) . . ?
F14 C14 C15 120.5(3) . . ?
F14 C14 C13 120.2(3) . . ?
C15 C14 C13 119.2(3) . . ?
F15 C15 C16 120.7(3) . . ?
F15 C15 C14 119.4(3) . . ?
C16 C15 C14 119.9(3) . . ?
F16 C16 C15 117.9(3) . . ?
F16 C16 C11 119.3(3) . . ?
C15 C16 C11 122.8(3) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 O21 H21 111(3) . . ?
O21 C21 H21A 109.5 . . ?
O21 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O21 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 N1 C1 C2 -71.9(3) . . . . ?
C17 N1 C1 C2 170.5(2) . . . . ?
C3 N1 C1 C2 50.7(3) . . . . ?
C19 N2 C2 C1 -71.2(3) . . . . ?
C20 N2 C2 C1 172.2(2) . . . . ?
C10 N2 C2 C1 52.4(3) . . . . ?
N1 C1 C2 N2 155.5(2) . . . . ?
C18 N1 C3 C4 -64.9(3) . . . . ?
C17 N1 C3 C4 56.8(3) . . . . ?
C1 N1 C3 C4 173.1(3) . . . . ?
N1 C3 C4 C9 -91.7(3) . . . . ?
N1 C3 C4 C5 92.2(4) . . . . ?
C9 C4 C5 F5 -176.2(3) . . . . ?
C3 C4 C5 F5 0.0(4) . . . . ?
C9 C4 C5 C6 2.9(4) . . . . ?
C3 C4 C5 C6 179.1(3) . . . . ?
F5 C5 C6 F6 -0.7(4) . . . . ?
C4 C5 C6 F6 -179.9(3) . . . . ?
F5 C5 C6 C7 178.3(3) . . . . ?
C4 C5 C6 C7 -0.8(5) . . . . ?
F6 C6 C7 F7 -0.9(4) . . . . ?
C5 C6 C7 F7 -180.0(3) . . . . ?
F6 C6 C7 C8 177.7(3) . . . . ?
C5 C6 C7 C8 -1.4(5) . . . . ?
F7 C7 C8 F8 2.1(5) . . . . ?
C6 C7 C8 F8 -176.5(3) . . . . ?
F7 C7 C8 C9 179.9(3) . . . . ?
C6 C7 C8 C9 1.3(5) . . . . ?
C5 C4 C9 F9 175.0(3) . . . . ?
C3 C4 C9 F9 -1.2(4) . . . . ?
C5 C4 C9 C8 -3.0(5) . . . . ?
C3 C4 C9 C8 -179.3(3) . . . . ?
F8 C8 C9 F9 0.7(5) . . . . ?
C7 C8 C9 F9 -177.1(3) . . . . ?
F8 C8 C9 C4 178.8(3) . . . . ?
C7 C8 C9 C4 0.9(5) . . . . ?
C19 N2 C10 C11 -68.2(3) . . . . ?
C20 N2 C10 C11 53.0(3) . . . . ?
C2 N2 C10 C11 169.5(2) . . . . ?
N2 C10 C11 C12 88.1(3) . . . . ?
N2 C10 C11 C16 -95.6(3) . . . . ?
C16 C11 C12 F12 -178.8(3) . . . . ?
C10 C11 C12 F12 -2.2(4) . . . . ?
C16 C11 C12 C13 2.2(5) . . . . ?
C10 C11 C12 C13 178.8(3) . . . . ?
F12 C12 C13 F13 -1.9(5) . . . . ?
C11 C12 C13 F13 177.1(3) . . . . ?
F12 C12 C13 C14 179.0(3) . . . . ?
C11 C12 C13 C14 -2.0(5) . . . . ?
F13 C13 C14 F14 1.1(5) . . . . ?
C12 C13 C14 F14 -179.8(3) . . . . ?
F13 C13 C14 C15 -178.7(3) . . . . ?
C12 C13 C14 C15 0.5(5) . . . . ?
F14 C14 C15 F15 -0.1(5) . . . . ?
C13 C14 C15 F15 179.6(3) . . . . ?
F14 C14 C15 C16 -179.1(3) . . . . ?
C13 C14 C15 C16 0.7(5) . . . . ?
F15 C15 C16 F16 0.9(5) . . . . ?
C14 C15 C16 F16 179.8(3) . . . . ?
F15 C15 C16 C11 -179.4(3) . . . . ?
C14 C15 C16 C11 -0.5(5) . . . . ?
C12 C11 C16 F16 178.8(3) . . . . ?
C10 C11 C16 F16 2.2(5) . . . . ?
C12 C11 C16 C15 -1.0(5) . . . . ?
C10 C11 C16 C15 -177.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O21 H21 Br2 0.883(19) 2.46(2) 3.316(3) 164(4) 4_566

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.084

_iucr_refine_instructions_details 
;
TITL mm-cb-42-2b in P 21/c
CELL   0.71073  13.2107   7.1955  25.9512  90.000  91.149  90.000
ZERR     4       0.0003   0.0001   0.0006   0.000   0.001   0.000
LATT  1
SYMM -X,1/2+Y,1/2-Z
SFAC        C       H       N       O       F       BR
UNIT        84      96      8       4       40      8
L.S.      10
OMIT -3 50.5
OMIT 1 0 0
OMIT -1 0 2
TEMP  -150
SIZE  0.22 0.18 0.04
EQIV $1 x, -y+1/2, z+1/2
HTAB O21 Br2_$1
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.013000    1.208200
FVAR       0.25511
MOLE 1
BR1   6    0.474368    0.695214    0.697216    11.00000    0.02673    0.01528 =
         0.01907   -0.00025   -0.00374   -0.00057
BR2   6    0.266933    0.123254    0.512164    11.00000    0.02775    0.02173 =
         0.01913   -0.00184   -0.00331    0.00366
F5    5    0.542388    0.286100    0.484699    11.00000    0.02476    0.02672 =
         0.01953   -0.00105   -0.00455   -0.00903
F6    5    0.698597    0.309550    0.419995    11.00000    0.04532    0.02772 =
         0.01557   -0.00018    0.00728    0.00090
F7    5    0.883153    0.421526    0.455387    11.00000    0.02742    0.04839 =
         0.03416    0.01447    0.01900    0.00785
F8    5    0.908952    0.523852    0.555908    11.00000    0.01736    0.06294 =
         0.04064    0.01306   -0.00247   -0.01655
F9    5    0.752423    0.500572    0.620584    11.00000    0.02908    0.04786 =
         0.02154   -0.00366   -0.00276   -0.01772
F12   5    0.229298   -0.062236    0.770584    11.00000    0.02730    0.01648 =
         0.02206    0.00203    0.00418    0.00496
F13   5    0.062660   -0.086452    0.828384    11.00000    0.03176    0.02486 =
         0.02652    0.00519    0.00764   -0.00922
F14   5   -0.048856    0.221792    0.847644    11.00000    0.01819    0.03984 =
         0.02568   -0.00214    0.01025   -0.00494
F15   5    0.003922    0.552558    0.806022    11.00000    0.02634    0.02781 =
         0.02519   -0.00349    0.00439    0.01137
F16   5    0.166972    0.577772    0.746094    11.00000    0.03312    0.01402 =
         0.02412    0.00207    0.00684    0.00223
N1    3    0.549014    0.182078    0.619206    11.00000    0.01459    0.01347 =
         0.01266    0.00098    0.00303   -0.00032
N2    3    0.277361    0.226271    0.666477    11.00000    0.01071    0.01367 =
         0.01530   -0.00100    0.00261   -0.00159
C1    1    0.467357    0.198636    0.659541    11.00000    0.01342    0.01633 =
         0.01023   -0.00019    0.00596   -0.00053
AFIX  23
H1A   2    0.492273    0.278766    0.688095    11.00000   -1.20000
H1B   2    0.453105    0.074100    0.673899    11.00000   -1.20000
AFIX   0
C2    1    0.369921    0.280571    0.636755    11.00000    0.01637    0.01139 =
         0.01290    0.00021    0.00404   -0.00052
AFIX  23
H2A   2    0.375620    0.417749    0.636347    11.00000   -1.20000
H2B   2    0.361449    0.237982    0.600651    11.00000   -1.20000
AFIX   0
C3    1    0.558551    0.369775    0.592013    11.00000    0.01909    0.01240 =
         0.01689    0.00075    0.00314   -0.00101
AFIX  23
H3A   2    0.494732    0.395375    0.572655    11.00000   -1.20000
H3B   2    0.567153    0.468125    0.618416    11.00000   -1.20000
AFIX   0
C4    1    0.645286    0.380783    0.555390    11.00000    0.01689    0.01341 =
         0.01367   -0.00053    0.00156   -0.00106
C5    1    0.633763    0.338836    0.503615    11.00000    0.01713    0.00947 =
         0.01991    0.00032   -0.00342   -0.00068
C6    1    0.712797    0.351330    0.470159    11.00000    0.02956    0.01302 =
         0.01295    0.00219    0.00278    0.00112
C7    1    0.805643    0.408960    0.487970    11.00000    0.01482    0.02557 =
         0.02474    0.01042    0.01016    0.00408
C8    1    0.819840    0.458318    0.538986    11.00000    0.01163    0.02772 =
         0.03119    0.01071   -0.00315   -0.00366
C9    1    0.738949    0.444181    0.571371    11.00000    0.02508    0.02431 =
         0.01414   -0.00162    0.00280   -0.00699
C10   1    0.295615    0.272545    0.723368    11.00000    0.01779    0.01566 =
         0.01314   -0.00083    0.00128   -0.00081
AFIX  23
H10A  2    0.348025    0.187520    0.737615    11.00000   -1.20000
H10B  2    0.322336    0.400780    0.726116    11.00000   -1.20000
AFIX   0
C11   1    0.202927    0.257504    0.755364    11.00000    0.01386    0.01752 =
         0.00944   -0.00107   -0.00089   -0.00250
C12   1    0.174385    0.092398    0.778345    11.00000    0.01578    0.01674 =
         0.01144   -0.00114   -0.00287    0.00330
C13   1    0.090509    0.077793    0.808535    11.00000    0.02166    0.01991 =
         0.01535    0.00385   -0.00326   -0.00602
C14   1    0.032772    0.233973    0.818165    11.00000    0.01619    0.02913 =
         0.01294   -0.00181    0.00389   -0.00244
C15   1    0.060109    0.400808    0.796991    11.00000    0.01992    0.02052 =
         0.01551   -0.00651   -0.00116    0.00709
C16   1    0.143099    0.410751    0.766245    11.00000    0.01863    0.01611 =
         0.01325    0.00074   -0.00135   -0.00288
C17   1    0.644811    0.131834    0.648217    11.00000    0.01261    0.02234 =
         0.02162    0.00449   -0.00130    0.00473
AFIX  33
H17A  2    0.662127    0.230967    0.672743    11.00000   -1.50000
H17B  2    0.699962    0.116573    0.623874    11.00000   -1.50000
H17C  2    0.634781    0.015215    0.666941    11.00000   -1.50000
AFIX   0
C18   1    0.523992    0.028827    0.581738    11.00000    0.02262    0.01517 =
         0.01635   -0.00502    0.00065   -0.00153
AFIX  33
H18A  2    0.461600    0.059845    0.562562    11.00000   -1.50000
H18B  2    0.514473   -0.087666    0.600596    11.00000   -1.50000
H18C  2    0.579585    0.014352    0.557620    11.00000   -1.50000
AFIX   0
C19   1    0.253499    0.023522    0.658047    11.00000    0.02095    0.01210 =
         0.01894   -0.00323    0.00285   -0.00349
AFIX  33
H19A  2    0.193666   -0.010309    0.677702    11.00000   -1.50000
H19B  2    0.311280   -0.052097    0.669666    11.00000   -1.50000
H19C  2    0.240041    0.001174    0.621293    11.00000   -1.50000
AFIX   0
C20   1    0.190897    0.338962    0.643920    11.00000    0.01364    0.02402 =
         0.01690    0.00312    0.00050    0.00529
AFIX  33
H20A  2    0.204496    0.471548    0.649225    11.00000   -1.50000
H20B  2    0.127993    0.305101    0.660968    11.00000   -1.50000
H20C  2    0.184061    0.313406    0.606921    11.00000   -1.50000
AFIX   0
MOLE 2
O21   4    0.132243    0.503693    0.908860    11.00000    0.03311    0.06664 =
         0.02420    0.01196   -0.00033    0.00382
H21   2    0.173799    0.452988    0.931912    11.00000   -1.50000
DFIX 0.91 O21 H21
C21   1    0.039212    0.555240    0.931154    11.00000    0.03889    0.05954 =
         0.02436    0.00034   -0.00359   -0.00362
AFIX 133
H21A  2    0.052253    0.606950    0.965586    11.00000   -1.50000
H21B  2   -0.004339    0.445558    0.933852    11.00000   -1.50000
H21C  2    0.005436    0.648834    0.909429    11.00000   -1.50000
HKLF   4
 
REM  mm-cb-42-2b in P 21/c
REM R1 =  0.0336 for   3527 Fo > 4sig(Fo)  and  0.0498 for all   4457 data
REM    328 parameters refined using      1 restraints
 
END
 
WGHT      0.0131      1.2186
REM Highest difference peak  0.354,  deepest hole -0.363,  1-sigma level  0.084
Q1    1   0.5458  0.6975  0.7223  11.00000  0.05    0.35
Q2    1   0.9809  0.4082  0.5092  11.00000  0.05    0.34
Q3    1   0.2009  0.6766  0.6779  11.00000  0.05    0.33
Q4    1   0.2694  0.0832  0.5519  11.00000  0.05    0.33
Q5    1  -0.0424  0.3706  0.7697  11.00000  0.05    0.32
Q6    1   0.6948  0.3472  0.5605  11.00000  0.05    0.31
Q7    1   0.3190 -0.0104  0.4986  11.00000  0.05    0.31
Q8    1   0.5732  0.4219  0.6140  11.00000  0.05    0.30
Q9    1   0.9191  0.7190  0.5826  11.00000  0.05    0.30
Q10   1   0.4819  0.3924  0.4503  11.00000  0.05    0.30
Q11   1   0.1939  0.4238  0.9797  11.00000  0.05    0.30
Q12   1   0.7842  0.4170  0.5558  11.00000  0.05    0.30
Q13   1   0.1763  0.6290  0.9592  11.00000  0.05    0.30
Q14   1   0.2332  0.2808  0.6495  11.00000  0.05    0.29
Q15   1   0.8199  0.3952  0.5181  11.00000  0.05    0.29
Q16   1   0.3795  0.5402  0.6069  11.00000  0.05    0.29
Q17   1   0.8029  0.4926  0.5084  11.00000  0.05    0.28
Q18   1   0.5398  0.8379  0.6825  11.00000  0.05    0.28
Q19   1   0.3358  0.1241  0.5387  11.00000  0.05    0.28
Q20   1   0.6332  0.3272  0.5783  11.00000  0.05    0.28
Q21   1   0.1211  0.2131  0.5091  11.00000  0.05    0.28
Q22   1   0.8999  0.4600  0.5819  11.00000  0.05    0.28
Q23   1   0.5999  0.4107  0.5696  11.00000  0.05    0.28
Q24   1   0.9239  0.5397  0.5012  11.00000  0.05    0.28
Q25   1   0.6827  0.3612  0.4919  11.00000  0.05    0.27
;
_database_code_depnum_ccdc_archive 'CCDC 1005285'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-pg-77-2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H18 F4 N, Br'
_chemical_formula_sum            'C13 H18 Br F4 N'
_chemical_formula_weight         344.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pca21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   14.1641(2)
_cell_length_b                   18.5407(3)
_cell_length_c                   10.9050(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2863.79(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3972
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_absorpt_coefficient_mu    2.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5946
_exptl_absorpt_correction_T_max  0.8928
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            35549
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         25.25
_reflns_number_total             5158
_reflns_number_gt                4704
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+3.0439P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.090(7)
_refine_ls_number_reflns         5158
_refine_ls_number_parameters     344
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0608
_refine_ls_wR_factor_gt          0.0583
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.61140(2) 0.897181(17) 0.50463(3) 0.02285(8) Uani 1 1 d . . .
Br2 Br -0.09457(2) 0.58701(2) 0.68153(3) 0.02808(9) Uani 1 1 d . . .
F9 F 0.45428(14) 0.93442(10) 0.76169(18) 0.0254(5) Uani 1 1 d . . .
F10 F 0.44009(13) 0.79887(9) 0.6747(2) 0.0283(4) Uani 1 1 d . . .
F11 F 0.32571(14) 0.76909(9) 0.4828(2) 0.0314(5) Uani 1 1 d . . .
F12 F 0.21873(15) 0.87465(11) 0.3826(2) 0.0327(5) Uani 1 1 d . . .
N1 N 0.4130(2) 1.10535(14) 0.6042(3) 0.0178(6) Uani 1 1 d . . .
C1 C 0.5143(2) 1.07761(18) 0.6023(3) 0.0211(7) Uani 1 1 d . . .
H1A H 0.5137 1.0271 0.5730 0.025 Uiso 1 1 calc R . .
H1B H 0.5505 1.1064 0.5419 0.025 Uiso 1 1 calc R . .
C2 C 0.5658(3) 1.0802(2) 0.7241(4) 0.0302(9) Uani 1 1 d . . .
H2A H 0.6299 1.0612 0.7138 0.045 Uiso 1 1 calc R . .
H2B H 0.5318 1.0509 0.7844 0.045 Uiso 1 1 calc R . .
H2C H 0.5691 1.1302 0.7529 0.045 Uiso 1 1 calc R . .
C3 C 0.4083(2) 1.17624(15) 0.6731(4) 0.0199(7) Uani 1 1 d . . .
H3A H 0.4294 1.1679 0.7584 0.024 Uiso 1 1 calc R . .
H3B H 0.4534 1.2103 0.6349 0.024 Uiso 1 1 calc R . .
C4 C 0.3119(2) 1.21159(17) 0.6766(4) 0.0278(8) Uani 1 1 d . . .
H4A H 0.2722 1.1871 0.7374 0.042 Uiso 1 1 calc R . .
H4B H 0.2823 1.2081 0.5956 0.042 Uiso 1 1 calc R . .
H4C H 0.3187 1.2625 0.6992 0.042 Uiso 1 1 calc R . .
C5 C 0.3806(2) 1.11425(18) 0.4713(3) 0.0214(8) Uani 1 1 d . . .
H5A H 0.3987 1.0704 0.4251 0.026 Uiso 1 1 calc R . .
H5B H 0.3108 1.1173 0.4703 0.026 Uiso 1 1 calc R . .
C6 C 0.4200(3) 1.17979(19) 0.4045(4) 0.0277(9) Uani 1 1 d . . .
H6A H 0.3955 1.1808 0.3204 0.042 Uiso 1 1 calc R . .
H6B H 0.4891 1.1769 0.4025 0.042 Uiso 1 1 calc R . .
H6C H 0.4008 1.2238 0.4475 0.042 Uiso 1 1 calc R . .
C7 C 0.3476(2) 1.05209(15) 0.6693(3) 0.0189(7) Uani 1 1 d . . .
H7A H 0.3676 1.0483 0.7560 0.023 Uiso 1 1 calc R . .
H7B H 0.2828 1.0721 0.6686 0.023 Uiso 1 1 calc R . .
C8 C 0.3445(2) 0.97727(18) 0.6155(3) 0.0176(7) Uani 1 1 d . . .
C9 C 0.3969(2) 0.92226(17) 0.6669(3) 0.0194(7) Uani 1 1 d . . .
C10 C 0.3901(2) 0.85186(17) 0.6225(3) 0.0192(7) Uani 1 1 d . . .
C11 C 0.3310(2) 0.83670(16) 0.5263(3) 0.0214(8) Uani 1 1 d . . .
C12 C 0.2778(2) 0.89106(19) 0.4766(3) 0.0229(8) Uani 1 1 d . . .
C13 C 0.2831(2) 0.96058(16) 0.5196(3) 0.0197(7) Uani 1 1 d . . .
H13 H 0.2450 0.9972 0.4841 0.024 Uiso 1 1 calc R . .
F9A F 0.20369(17) 0.54695(12) 0.7628(2) 0.0382(5) Uani 1 1 d . . .
F10A F 0.18288(18) 0.68916(12) 0.7595(2) 0.0433(6) Uani 1 1 d . . .
F11A F 0.12883(16) 0.75751(10) 0.5513(2) 0.0400(6) Uani 1 1 d . . .
F12A F 0.10117(17) 0.68120(11) 0.3435(2) 0.0414(6) Uani 1 1 d . . .
N1A N 0.08925(19) 0.41084(14) 0.5937(3) 0.0174(7) Uani 1 1 d . . .
C1A C 0.0060(2) 0.43070(16) 0.5130(3) 0.0200(7) Uani 1 1 d . . .
H1A1 H -0.0111 0.4815 0.5295 0.024 Uiso 1 1 calc R . .
H1A2 H 0.0262 0.4275 0.4263 0.024 Uiso 1 1 calc R . .
C2A C -0.0813(3) 0.3845(2) 0.5298(4) 0.0353(10) Uani 1 1 d . . .
H2A1 H -0.1311 0.4013 0.4743 0.053 Uiso 1 1 calc R . .
H2A2 H -0.1032 0.3881 0.6148 0.053 Uiso 1 1 calc R . .
H2A3 H -0.0660 0.3341 0.5110 0.053 Uiso 1 1 calc R . .
C3A C 0.1148(3) 0.33155(17) 0.5832(3) 0.0243(8) Uani 1 1 d . . .
H3A1 H 0.1728 0.3229 0.6317 0.029 Uiso 1 1 calc R . .
H3A2 H 0.0635 0.3028 0.6208 0.029 Uiso 1 1 calc R . .
C4A C 0.1310(3) 0.30413(19) 0.4551(4) 0.0391(11) Uani 1 1 d . . .
H4A1 H 0.1464 0.2526 0.4580 0.059 Uiso 1 1 calc R . .
H4A2 H 0.1834 0.3306 0.4176 0.059 Uiso 1 1 calc R . .
H4A3 H 0.0736 0.3113 0.4063 0.059 Uiso 1 1 calc R . .
C5A C 0.0633(3) 0.4265(2) 0.7265(3) 0.0211(8) Uani 1 1 d . . .
H5A1 H 0.0552 0.4793 0.7359 0.025 Uiso 1 1 calc R . .
H5A2 H 0.0017 0.4036 0.7442 0.025 Uiso 1 1 calc R . .
C6A C 0.1340(3) 0.4009(2) 0.8213(3) 0.0285(9) Uani 1 1 d . . .
H6A1 H 0.1114 0.4136 0.9035 0.043 Uiso 1 1 calc R . .
H6A2 H 0.1951 0.4241 0.8065 0.043 Uiso 1 1 calc R . .
H6A3 H 0.1412 0.3485 0.8152 0.043 Uiso 1 1 calc R . .
C7A C 0.1748(2) 0.45520(17) 0.5536(3) 0.0192(7) Uani 1 1 d . . .
H7A1 H 0.2284 0.4434 0.6081 0.023 Uiso 1 1 calc R . .
H7A2 H 0.1925 0.4404 0.4694 0.023 Uiso 1 1 calc R . .
C8A C 0.1605(2) 0.53575(18) 0.5548(3) 0.0186(7) Uani 1 1 d . . .
C9A C 0.1773(2) 0.57690(18) 0.6575(3) 0.0250(8) Uani 1 1 d . . .
C10A C 0.1669(3) 0.65158(18) 0.6575(4) 0.0289(9) Uani 1 1 d . . .
C11A C 0.1403(3) 0.68583(19) 0.5515(4) 0.0276(9) Uani 1 1 d . . .
C12A C 0.1255(3) 0.6458(2) 0.4470(4) 0.0284(9) Uani 1 1 d . . .
C13A C 0.1348(2) 0.57177(19) 0.4469(4) 0.0233(8) Uani 1 1 d . . .
H13A H 0.1238 0.5452 0.3738 0.028 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02001(14) 0.01897(15) 0.02958(19) -0.00166(17) 0.00087(16) -0.00073(13)
Br2 0.02287(16) 0.0373(2) 0.02410(19) -0.00962(19) -0.00371(18) 0.00777(16)
F9 0.0320(12) 0.0192(11) 0.0250(11) 0.0014(8) -0.0086(10) -0.0002(8)
F10 0.0341(10) 0.0145(9) 0.0363(11) 0.0039(10) -0.0091(11) 0.0063(8)
F11 0.0367(11) 0.0155(9) 0.0420(15) -0.0066(9) -0.0076(10) 0.0037(8)
F12 0.0396(13) 0.0244(11) 0.0340(13) -0.0063(9) -0.0179(11) 0.0003(9)
N1 0.0173(14) 0.0158(15) 0.0203(17) -0.0002(12) 0.0035(13) -0.0001(11)
C1 0.0169(17) 0.0184(17) 0.028(2) -0.0010(15) 0.0035(15) 0.0026(14)
C2 0.0227(18) 0.027(2) 0.041(3) -0.0004(17) -0.0044(16) 0.0035(16)
C3 0.0230(15) 0.0123(14) 0.0243(18) -0.0032(16) 0.0007(17) -0.0002(13)
C4 0.0275(17) 0.0186(16) 0.037(2) -0.0059(19) -0.001(2) 0.0026(14)
C5 0.0224(17) 0.0159(17) 0.026(2) 0.0023(14) 0.0002(15) -0.0012(14)
C6 0.032(2) 0.0226(19) 0.029(2) 0.0056(16) -0.0009(17) -0.0029(16)
C7 0.0208(16) 0.0148(15) 0.0210(19) -0.0004(15) -0.0001(16) -0.0005(12)
C8 0.0171(16) 0.0191(17) 0.0166(18) 0.0024(14) 0.0039(14) 0.0016(14)
C9 0.0194(15) 0.0211(16) 0.0175(19) 0.0014(15) -0.0009(16) -0.0045(13)
C10 0.0205(17) 0.0164(17) 0.0207(18) 0.0060(14) 0.0044(15) 0.0015(14)
C11 0.0243(17) 0.0143(16) 0.025(2) -0.0028(14) 0.0001(16) -0.0018(13)
C12 0.0212(17) 0.0245(18) 0.023(2) -0.0006(15) -0.0046(15) -0.0006(14)
C13 0.0183(15) 0.0193(16) 0.0216(19) 0.0023(15) -0.0003(15) 0.0022(12)
F9A 0.0478(14) 0.0364(12) 0.0304(13) -0.0019(10) -0.0108(11) -0.0002(11)
F10A 0.0637(16) 0.0307(12) 0.0356(13) -0.0156(10) 0.0041(12) -0.0061(11)
F11A 0.0337(12) 0.0183(11) 0.0679(17) -0.0031(10) 0.0018(11) 0.0000(9)
F12A 0.0521(14) 0.0261(11) 0.0461(14) 0.0157(10) -0.0167(12) -0.0073(11)
N1A 0.0184(15) 0.0159(15) 0.0180(18) 0.0016(11) 0.0013(12) -0.0008(11)
C1A 0.0245(16) 0.0179(14) 0.0176(17) -0.0006(15) -0.0067(17) 0.0010(13)
C2A 0.0317(19) 0.035(2) 0.039(3) 0.0090(18) -0.0130(18) -0.0134(16)
C3A 0.034(2) 0.0128(17) 0.026(2) 0.0042(15) 0.0007(16) 0.0025(15)
C4A 0.067(3) 0.0121(18) 0.039(2) -0.0029(16) 0.005(2) 0.0044(18)
C5A 0.0259(19) 0.0246(18) 0.0129(19) 0.0005(14) 0.0029(15) -0.0015(15)
C6A 0.034(2) 0.034(2) 0.0179(19) 0.0046(17) 0.0005(17) 0.0036(18)
C7A 0.0176(17) 0.0223(18) 0.0177(17) 0.0017(14) 0.0040(14) 0.0007(14)
C8A 0.0155(16) 0.0210(18) 0.0193(18) -0.0008(15) 0.0017(14) -0.0011(14)
C9A 0.0233(17) 0.0266(18) 0.025(2) 0.0008(16) -0.0006(16) -0.0015(14)
C10A 0.0293(19) 0.0224(18) 0.035(3) -0.0165(17) 0.0074(17) -0.0081(14)
C11A 0.0224(18) 0.0156(18) 0.045(2) 0.0015(17) 0.0075(17) 0.0000(14)
C12A 0.0234(19) 0.026(2) 0.036(2) 0.0092(18) -0.0005(17) -0.0057(16)
C13A 0.0163(17) 0.0234(19) 0.030(2) -0.0001(16) 0.0039(15) -0.0019(14)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F9 C9 1.334(4) . ?
F10 C10 1.338(4) . ?
F11 C11 1.342(4) . ?
F12 C12 1.357(4) . ?
N1 C3 1.515(4) . ?
N1 C1 1.525(4) . ?
N1 C7 1.529(4) . ?
N1 C5 1.529(5) . ?
C1 C2 1.517(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.515(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.523(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.507(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.380(5) . ?
C8 C13 1.395(5) . ?
C9 C10 1.396(5) . ?
C10 C11 1.371(5) . ?
C11 C12 1.370(5) . ?
C12 C13 1.374(5) . ?
C13 H13 0.9500 . ?
F9A C9A 1.328(4) . ?
F10A C10A 1.332(4) . ?
F11A C11A 1.339(4) . ?
F12A C12A 1.350(4) . ?
N1A C1A 1.516(4) . ?
N1A C3A 1.518(4) . ?
N1A C5A 1.522(4) . ?
N1A C7A 1.528(4) . ?
C1A C2A 1.516(5) . ?
C1A H1A1 0.9900 . ?
C1A H1A2 0.9900 . ?
C2A H2A1 0.9800 . ?
C2A H2A2 0.9800 . ?
C2A H2A3 0.9800 . ?
C3A C4A 1.503(5) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4A H4A1 0.9800 . ?
C4A H4A2 0.9800 . ?
C4A H4A3 0.9800 . ?
C5A C6A 1.515(5) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A H6A1 0.9800 . ?
C6A H6A2 0.9800 . ?
C6A H6A3 0.9800 . ?
C7A C8A 1.507(5) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A C9A 1.376(5) . ?
C8A C13A 1.401(5) . ?
C9A C10A 1.393(5) . ?
C10A C11A 1.372(6) . ?
C11A C12A 1.375(5) . ?
C12A C13A 1.379(5) . ?
C13A H13A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C1 109.9(3) . . ?
C3 N1 C7 107.7(3) . . ?
C1 N1 C7 111.0(2) . . ?
C3 N1 C5 111.3(3) . . ?
C1 N1 C5 107.8(3) . . ?
C7 N1 C5 109.2(3) . . ?
C2 C1 N1 115.5(3) . . ?
C2 C1 H1A 108.4 . . ?
N1 C1 H1A 108.4 . . ?
C2 C1 H1B 108.4 . . ?
N1 C1 H1B 108.4 . . ?
H1A C1 H1B 107.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 N1 115.3(3) . . ?
C4 C3 H3A 108.4 . . ?
N1 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
N1 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N1 115.5(3) . . ?
C6 C5 H5A 108.4 . . ?
N1 C5 H5A 108.4 . . ?
C6 C5 H5B 108.4 . . ?
N1 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N1 115.5(3) . . ?
C8 C7 H7A 108.4 . . ?
N1 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
N1 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C13 118.4(3) . . ?
C9 C8 C7 120.4(3) . . ?
C13 C8 C7 120.9(3) . . ?
F9 C9 C8 121.2(3) . . ?
F9 C9 C10 118.0(3) . . ?
C8 C9 C10 120.9(3) . . ?
F10 C10 C11 119.9(3) . . ?
F10 C10 C9 120.1(3) . . ?
C11 C10 C9 120.0(3) . . ?
F11 C11 C12 121.1(3) . . ?
F11 C11 C10 119.7(3) . . ?
C12 C11 C10 119.2(3) . . ?
F12 C12 C11 118.2(3) . . ?
F12 C12 C13 120.1(3) . . ?
C11 C12 C13 121.7(3) . . ?
C12 C13 C8 119.9(3) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C1A N1A C3A 112.1(3) . . ?
C1A N1A C5A 108.6(3) . . ?
C3A N1A C5A 108.3(3) . . ?
C1A N1A C7A 108.6(3) . . ?
C3A N1A C7A 108.1(3) . . ?
C5A N1A C7A 111.2(3) . . ?
C2A C1A N1A 115.3(3) . . ?
C2A C1A H1A1 108.5 . . ?
N1A C1A H1A1 108.5 . . ?
C2A C1A H1A2 108.5 . . ?
N1A C1A H1A2 108.5 . . ?
H1A1 C1A H1A2 107.5 . . ?
C1A C2A H2A1 109.5 . . ?
C1A C2A H2A2 109.5 . . ?
H2A1 C2A H2A2 109.5 . . ?
C1A C2A H2A3 109.5 . . ?
H2A1 C2A H2A3 109.5 . . ?
H2A2 C2A H2A3 109.5 . . ?
C4A C3A N1A 115.7(3) . . ?
C4A C3A H3A1 108.3 . . ?
N1A C3A H3A1 108.3 . . ?
C4A C3A H3A2 108.3 . . ?
N1A C3A H3A2 108.3 . . ?
H3A1 C3A H3A2 107.4 . . ?
C3A C4A H4A1 109.5 . . ?
C3A C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 109.5 . . ?
C3A C4A H4A3 109.5 . . ?
H4A1 C4A H4A3 109.5 . . ?
H4A2 C4A H4A3 109.5 . . ?
C6A C5A N1A 115.5(3) . . ?
C6A C5A H5A1 108.4 . . ?
N1A C5A H5A1 108.4 . . ?
C6A C5A H5A2 108.4 . . ?
N1A C5A H5A2 108.4 . . ?
H5A1 C5A H5A2 107.5 . . ?
C5A C6A H6A1 109.5 . . ?
C5A C6A H6A2 109.5 . . ?
H6A1 C6A H6A2 109.5 . . ?
C5A C6A H6A3 109.5 . . ?
H6A1 C6A H6A3 109.5 . . ?
H6A2 C6A H6A3 109.5 . . ?
C8A C7A N1A 115.1(3) . . ?
C8A C7A H7A1 108.5 . . ?
N1A C7A H7A1 108.5 . . ?
C8A C7A H7A2 108.5 . . ?
N1A C7A H7A2 108.5 . . ?
H7A1 C7A H7A2 107.5 . . ?
C9A C8A C13A 117.7(3) . . ?
C9A C8A C7A 122.2(3) . . ?
C13A C8A C7A 120.0(3) . . ?
F9A C9A C8A 121.3(3) . . ?
F9A C9A C10A 116.5(3) . . ?
C8A C9A C10A 122.2(3) . . ?
F10A C10A C11A 120.6(3) . . ?
F10A C10A C9A 120.1(3) . . ?
C11A C10A C9A 119.3(3) . . ?
F11A C11A C10A 119.6(4) . . ?
F11A C11A C12A 121.1(4) . . ?
C10A C11A C12A 119.4(3) . . ?
F12A C12A C11A 118.0(3) . . ?
F12A C12A C13A 120.5(4) . . ?
C11A C12A C13A 121.5(4) . . ?
C12A C13A C8A 119.9(3) . . ?
C12A C13A H13A 120.1 . . ?
C8A C13A H13A 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 C2 46.3(4) . . . . ?
C7 N1 C1 C2 -72.8(4) . . . . ?
C5 N1 C1 C2 167.7(3) . . . . ?
C1 N1 C3 C4 177.2(3) . . . . ?
C7 N1 C3 C4 -61.7(4) . . . . ?
C5 N1 C3 C4 57.9(4) . . . . ?
C3 N1 C5 C6 45.0(4) . . . . ?
C1 N1 C5 C6 -75.6(4) . . . . ?
C7 N1 C5 C6 163.7(3) . . . . ?
C3 N1 C7 C8 -178.6(3) . . . . ?
C1 N1 C7 C8 -58.2(4) . . . . ?
C5 N1 C7 C8 60.5(3) . . . . ?
N1 C7 C8 C9 99.0(4) . . . . ?
N1 C7 C8 C13 -86.4(4) . . . . ?
C13 C8 C9 F9 -177.6(3) . . . . ?
C7 C8 C9 F9 -2.9(5) . . . . ?
C13 C8 C9 C10 1.3(5) . . . . ?
C7 C8 C9 C10 176.1(3) . . . . ?
F9 C9 C10 F10 0.1(5) . . . . ?
C8 C9 C10 F10 -178.8(3) . . . . ?
F9 C9 C10 C11 179.1(3) . . . . ?
C8 C9 C10 C11 0.1(5) . . . . ?
F10 C10 C11 F11 -1.9(5) . . . . ?
C9 C10 C11 F11 179.1(3) . . . . ?
F10 C10 C11 C12 177.7(3) . . . . ?
C9 C10 C11 C12 -1.3(5) . . . . ?
F11 C11 C12 F12 0.6(5) . . . . ?
C10 C11 C12 F12 -179.0(3) . . . . ?
F11 C11 C12 C13 -179.5(3) . . . . ?
C10 C11 C12 C13 0.9(5) . . . . ?
F12 C12 C13 C8 -179.5(3) . . . . ?
C11 C12 C13 C8 0.6(5) . . . . ?
C9 C8 C13 C12 -1.7(5) . . . . ?
C7 C8 C13 C12 -176.4(3) . . . . ?
C3A N1A C1A C2A 53.0(4) . . . . ?
C5A N1A C1A C2A -66.7(4) . . . . ?
C7A N1A C1A C2A 172.3(3) . . . . ?
C1A N1A C3A C4A 53.0(4) . . . . ?
C5A N1A C3A C4A 172.8(3) . . . . ?
C7A N1A C3A C4A -66.6(4) . . . . ?
C1A N1A C5A C6A 172.5(3) . . . . ?
C3A N1A C5A C6A 50.6(4) . . . . ?
C7A N1A C5A C6A -68.1(4) . . . . ?
C1A N1A C7A C8A 56.4(4) . . . . ?
C3A N1A C7A C8A 178.2(3) . . . . ?
C5A N1A C7A C8A -63.0(4) . . . . ?
N1A C7A C8A C9A 88.2(4) . . . . ?
N1A C7A C8A C13A -95.8(4) . . . . ?
C13A C8A C9A F9A -178.7(3) . . . . ?
C7A C8A C9A F9A -2.7(5) . . . . ?
C13A C8A C9A C10A 1.9(5) . . . . ?
C7A C8A C9A C10A 178.0(3) . . . . ?
F9A C9A C10A F10A -0.2(5) . . . . ?
C8A C9A C10A F10A 179.2(3) . . . . ?
F9A C9A C10A C11A 179.7(3) . . . . ?
C8A C9A C10A C11A -1.0(5) . . . . ?
F10A C10A C11A F11A -1.1(5) . . . . ?
C9A C10A C11A F11A 179.0(3) . . . . ?
F10A C10A C11A C12A 179.1(3) . . . . ?
C9A C10A C11A C12A -0.8(5) . . . . ?
F11A C11A C12A F12A 1.5(5) . . . . ?
C10A C11A C12A F12A -178.8(3) . . . . ?
F11A C11A C12A C13A -178.3(3) . . . . ?
C10A C11A C12A C13A 1.5(6) . . . . ?
F12A C12A C13A C8A 179.8(3) . . . . ?
C11A C12A C13A C8A -0.5(5) . . . . ?
C9A C8A C13A C12A -1.2(5) . . . . ?
C7A C8A C13A C12A -177.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.059

_iucr_refine_instructions_details 
;
TITL mm-pg-77-2 in P 21 a b
REM  transformed to space group : Pca21
CELL   0.71073 14.1641 18.5407 10.9050   90.000   90.000   90.000
ZERR   8        0.0002  0.0003  0.0002    0.000    0.000    0.000
LATT   -1
SYMM   -X,-Y,1/2+Z
SYMM   1/2-X,+Y,1/2+Z
SYMM   1/2+X,-Y,+Z
SFAC        C       H       N       F       BR
UNIT       104     144       8      32       8
L.S.      10
OMIT -3 50.5
TEMP  -150
SIZE  0.2 0.18 0.04
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.000000    3.043900
FVAR       0.29374
BR1   5    0.611399    0.897181    0.504632    11.00000    0.02001    0.01897 =
         0.02958   -0.00166    0.00087   -0.00073
BR2   5   -0.094574    0.587009    0.681530    11.00000    0.02287    0.03726 =
         0.02410   -0.00962   -0.00371    0.00777
MOLE 1
F9    4    0.454281    0.934420    0.761693    11.00000    0.03202    0.01922 =
         0.02500    0.00137   -0.00859   -0.00022
F10   4    0.440095    0.798870    0.674722    11.00000    0.03407    0.01454 =
         0.03634    0.00394   -0.00908    0.00632
F11   4    0.325709    0.769085    0.482787    11.00000    0.03671    0.01552 =
         0.04199   -0.00664   -0.00759    0.00365
F12   4    0.218734    0.874651    0.382608    11.00000    0.03956    0.02444 =
         0.03398   -0.00629   -0.01793    0.00031
N1    3    0.412975    1.105345    0.604208    11.00000    0.01732    0.01582 =
         0.02026   -0.00019    0.00348   -0.00013
C1    1    0.514303    1.077614    0.602251    11.00000    0.01694    0.01839 =
         0.02789   -0.00101    0.00348    0.00259
AFIX  23
H1A   2    0.513712    1.027061    0.573034    11.00000   -1.20000
H1B   2    0.550539    1.106352    0.541925    11.00000   -1.20000
AFIX   0
C2    1    0.565827    1.080188    0.724122    11.00000    0.02266    0.02714 =
         0.04091   -0.00044   -0.00441    0.00352
AFIX  33
H2A   2    0.629882    1.061152    0.713790    11.00000   -1.50000
H2B   2    0.531755    1.050878    0.784406    11.00000   -1.50000
H2C   2    0.569133    1.130197    0.752903    11.00000   -1.50000
AFIX   0
C3    1    0.408265    1.176243    0.673068    11.00000    0.02299    0.01231 =
         0.02426   -0.00322    0.00067   -0.00021
AFIX  23
H3A   2    0.429408    1.167862    0.758418    11.00000   -1.20000
H3B   2    0.453360    1.210299    0.634881    11.00000   -1.20000
AFIX   0
C4    1    0.311857    1.211588    0.676631    11.00000    0.02748    0.01855 =
         0.03729   -0.00593   -0.00143    0.00264
AFIX 137
H4A   2    0.272208    1.187089    0.737367    11.00000   -1.50000
H4B   2    0.282276    1.208058    0.595613    11.00000   -1.50000
H4C   2    0.318731    1.262478    0.699215    11.00000   -1.50000
AFIX   0
C5    1    0.380590    1.114253    0.471317    11.00000    0.02235    0.01595 =
         0.02600    0.00225    0.00023   -0.00117
AFIX  23
H5A   2    0.398748    1.070435    0.425109    11.00000   -1.20000
H5B   2    0.310810    1.117260    0.470337    11.00000   -1.20000
AFIX   0
C6    1    0.420001    1.179788    0.404464    11.00000    0.03160    0.02264 =
         0.02899    0.00555   -0.00089   -0.00287
AFIX  33
H6A   2    0.395538    1.180798    0.320419    11.00000   -1.50000
H6B   2    0.489072    1.176929    0.402478    11.00000   -1.50000
H6C   2    0.400753    1.223806    0.447475    11.00000   -1.50000
AFIX   0
C7    1    0.347590    1.052089    0.669306    11.00000    0.02080    0.01484 =
         0.02098   -0.00040   -0.00009   -0.00055
AFIX  23
H7A   2    0.367628    1.048330    0.756044    11.00000   -1.20000
H7B   2    0.282802    1.072120    0.668568    11.00000   -1.20000
AFIX   0
C8    1    0.344525    0.977271    0.615503    11.00000    0.01709    0.01914 =
         0.01656    0.00240    0.00389    0.00164
C9    1    0.396888    0.922259    0.666934    11.00000    0.01944    0.02109 =
         0.01753    0.00143   -0.00091   -0.00445
C10   1    0.390111    0.851861    0.622452    11.00000    0.02048    0.01638 =
         0.02074    0.00600    0.00442    0.00152
C11   1    0.330999    0.836701    0.526254    11.00000    0.02433    0.01433 =
         0.02541   -0.00276    0.00011   -0.00175
C12   1    0.277806    0.891064    0.476565    11.00000    0.02125    0.02446 =
         0.02296   -0.00060   -0.00457   -0.00057
C13   1    0.283102    0.960583    0.519599    11.00000    0.01833    0.01932 =
         0.02159    0.00227   -0.00033    0.00224
AFIX  43
H13   2    0.245006    0.997229    0.484118    11.00000   -1.20000
AFIX   0
MOLE 2
F9A   4    0.203688    0.546951    0.762763    11.00000    0.04782    0.03636 =
         0.03043   -0.00191   -0.01084   -0.00019
F10A  4    0.182880    0.689158    0.759470    11.00000    0.06373    0.03072 =
         0.03556   -0.01562    0.00414   -0.00605
F11A  4    0.128829    0.757512    0.551297    11.00000    0.03373    0.01830 =
         0.06786   -0.00313    0.00177    0.00003
F12A  4    0.101171    0.681202    0.343513    11.00000    0.05211    0.02609 =
         0.04610    0.01570   -0.01672   -0.00733
N1A   3    0.089247    0.410840    0.593728    11.00000    0.01840    0.01587 =
         0.01800    0.00163    0.00127   -0.00085
C1A   1    0.006044    0.430700    0.513028    11.00000    0.02449    0.01789 =
         0.01763   -0.00059   -0.00667    0.00103
AFIX  23
H1A1  2   -0.011097    0.481550    0.529505    11.00000   -1.20000
H1A2  2    0.026172    0.427539    0.426256    11.00000   -1.20000
AFIX   0
C2A   1   -0.081286    0.384464    0.529762    11.00000    0.03172    0.03526 =
         0.03904    0.00897   -0.01298   -0.01338
AFIX  33
H2A1  2   -0.131095    0.401270    0.474317    11.00000   -1.50000
H2A2  2   -0.103220    0.388127    0.614766    11.00000   -1.50000
H2A3  2   -0.065998    0.334106    0.511022    11.00000   -1.50000
AFIX   0
C3A   1    0.114804    0.331550    0.583176    11.00000    0.03447    0.01281 =
         0.02561    0.00418    0.00070    0.00251
AFIX  23
H3A1  2    0.172789    0.322863    0.631666    11.00000   -1.20000
H3A2  2    0.063525    0.302808    0.620828    11.00000   -1.20000
AFIX   0
C4A   1    0.130953    0.304135    0.455145    11.00000    0.06675    0.01212 =
         0.03851   -0.00287    0.00496    0.00441
AFIX  33
H4A1  2    0.146358    0.252633    0.458047    11.00000   -1.50000
H4A2  2    0.183391    0.330640    0.417642    11.00000   -1.50000
H4A3  2    0.073638    0.311259    0.406283    11.00000   -1.50000
AFIX   0
C5A   1    0.063349    0.426518    0.726500    11.00000    0.02591    0.02458 =
         0.01293    0.00053    0.00293   -0.00153
AFIX  23
H5A1  2    0.055185    0.479257    0.735942    11.00000   -1.20000
H5A2  2    0.001680    0.403631    0.744151    11.00000   -1.20000
AFIX   0
C6A   1    0.133999    0.400906    0.821272    11.00000    0.03371    0.03389 =
         0.01790    0.00460    0.00051    0.00362
AFIX  33
H6A1  2    0.111422    0.413551    0.903455    11.00000   -1.50000
H6A2  2    0.195095    0.424139    0.806496    11.00000   -1.50000
H6A3  2    0.141182    0.348457    0.815174    11.00000   -1.50000
AFIX   0
C7A   1    0.174760    0.455197    0.553552    11.00000    0.01757    0.02231 =
         0.01774    0.00170    0.00397    0.00069
AFIX  23
H7A1  2    0.228445    0.443361    0.608093    11.00000   -1.20000
H7A2  2    0.192460    0.440394    0.469411    11.00000   -1.20000
AFIX   0
C8A   1    0.160471    0.535754    0.554826    11.00000    0.01554    0.02099 =
         0.01929   -0.00084    0.00166   -0.00107
C9A   1    0.177345    0.576901    0.657536    11.00000    0.02334    0.02661 =
         0.02508    0.00078   -0.00065   -0.00145
C10A  1    0.166902    0.651583    0.657467    11.00000    0.02932    0.02243 =
         0.03498   -0.01654    0.00741   -0.00813
C11A  1    0.140296    0.685828    0.551451    11.00000    0.02238    0.01558 =
         0.04484    0.00155    0.00745    0.00004
C12A  1    0.125540    0.645833    0.447001    11.00000    0.02337    0.02624 =
         0.03556    0.00920   -0.00049   -0.00569
C13A  1    0.134788    0.571768    0.446906    11.00000    0.01626    0.02344 =
         0.03028   -0.00008    0.00389   -0.00185
AFIX  43
H13A  2    0.123761    0.545221    0.373784    11.00000   -1.20000
HKLF   4
 
REM  mm-pg-77-2 in P 21 a b
REM R1 =  0.0285 for   4704 Fo > 4sig(Fo)  and  0.0346 for all   5158 data
REM    344 parameters refined using      1 restraints
 
END
 
WGHT      0.0000      3.0317
REM Highest difference peak  0.547,  deepest hole -0.273,  1-sigma level  0.059
Q1    1  -0.0771  0.6233  0.6391  11.00000  0.05    0.25
Q2    1   0.6009  1.1361  0.7351  11.00000  0.05    0.25
Q3    1   0.5437  1.0809  0.8043  11.00000  0.05    0.24
Q4    1   0.5961  1.0497  0.7196  11.00000  0.05    0.24
Q5    1   0.2033  0.3939  0.7878  11.00000  0.05    0.23
Q6    1   0.1434  0.7543  0.6438  11.00000  0.05    0.23
Q7    1  -0.0985  0.6369  0.6630  11.00000  0.05    0.23
Q8    1  -0.0976  0.3708  0.4584  11.00000  0.05    0.22
Q9    1   0.3970  0.9568  0.8028  11.00000  0.05    0.22
Q10   1   0.6198  0.9470  0.5174  11.00000  0.05    0.21
Q11   1   0.1185  0.3176  0.7366  11.00000  0.05    0.21
Q12   1   0.4228  1.1613  0.3043  11.00000  0.05    0.20
Q13   1   0.1310  0.5420  0.6162  11.00000  0.05    0.20
Q14   1  -0.1465  0.6515  0.6359  11.00000  0.05    0.20
Q15   1   0.6245  0.8423  0.5186  11.00000  0.05    0.20
Q16   1  -0.2009  0.6109  0.7363  11.00000  0.05    0.20
Q17   1   0.1780  0.3478  0.9987  11.00000  0.05    0.20
Q18   1   0.1614  0.5876  0.4346  11.00000  0.05    0.20
Q19   1  -0.1646  0.6328  0.7477  11.00000  0.05    0.19
Q20   1  -0.1299  0.4270  0.6221  11.00000  0.05    0.19
Q21   1  -0.2008  0.4507  0.6076  11.00000  0.05    0.19
Q22   1   0.3467  1.0120  0.6454  11.00000  0.05    0.19
Q23   1  -0.1201  0.4272  0.7125  11.00000  0.05    0.19
Q24   1   0.1191  0.4402  0.9409  11.00000  0.05    0.19
Q25   1   0.1462  0.6128  0.6661  11.00000  0.05    0.19
;
_database_code_depnum_ccdc_archive 'CCDC 1005286'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-md-22-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 F5 N2, Br'
_chemical_formula_sum            'C12 H8 Br F5 N2'
_chemical_formula_weight         355.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.4302(2)
_cell_length_b                   9.47480(10)
_cell_length_c                   23.7921(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.8540(10)
_cell_angle_gamma                90.00
_cell_volume                     2545.95(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6641
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.853
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_absorpt_coefficient_mu    3.280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2803
_exptl_absorpt_correction_T_max  0.8029
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8878
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         25.25
_reflns_number_total             4612
_reflns_number_gt                3867
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0107P)^2^+2.6120P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4612
_refine_ls_number_parameters     373
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0587
_refine_ls_wR_factor_gt          0.0550
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.25324(2) 0.39336(3) 0.485077(12) 0.02888(8) Uani 1 1 d . . .
Br2 Br 0.79585(2) 0.53950(3) 0.162898(11) 0.02383(8) Uani 1 1 d . . .
F8 F 0.24350(13) 0.72051(15) 0.34536(7) 0.0316(4) Uani 1 1 d . . .
F9 F 0.16158(14) 0.97833(16) 0.30774(7) 0.0350(4) Uani 1 1 d . . .
F10 F 0.27545(13) 1.21475(15) 0.35007(6) 0.0292(4) Uani 1 1 d . . .
F11 F 0.47519(13) 1.19313(14) 0.42825(6) 0.0272(3) Uani 1 1 d . . .
F12 F 0.56070(12) 0.93896(14) 0.46221(6) 0.0236(3) Uani 1 1 d . . .
N1 N 0.50640(18) 0.6100(2) 0.38077(8) 0.0187(4) Uani 1 1 d . . .
N2 N 0.6959(2) 0.7039(2) 0.27840(10) 0.0267(5) Uani 1 1 d D . .
H2A H 0.701(2) 0.7969(19) 0.2836(12) 0.032 Uiso 1 1 d D . .
H2B H 0.720(2) 0.665(3) 0.2493(9) 0.032 Uiso 1 1 d D . .
C1 C 0.5758(2) 0.6864(3) 0.35154(10) 0.0198(5) Uani 1 1 d . . .
H1 H 0.5881 0.7837 0.3600 0.024 Uiso 1 1 calc R . .
C2 C 0.6300(2) 0.6246(3) 0.30891(11) 0.0212(6) Uani 1 1 d . . .
C3 C 0.6133(3) 0.4795(3) 0.30039(12) 0.0319(7) Uani 1 1 d . . .
H3 H 0.6500 0.4325 0.2725 0.038 Uiso 1 1 calc R . .
C4 C 0.5440(3) 0.4047(3) 0.33224(13) 0.0392(8) Uani 1 1 d . . .
H4 H 0.5343 0.3059 0.3266 0.047 Uiso 1 1 calc R . .
C5 C 0.4882(3) 0.4718(3) 0.37239(12) 0.0307(7) Uani 1 1 d . . .
H5 H 0.4381 0.4208 0.3935 0.037 Uiso 1 1 calc R . .
C6 C 0.4505(2) 0.6809(2) 0.42631(11) 0.0202(5) Uani 1 1 d . . .
H6A H 0.5102 0.6925 0.4608 0.024 Uiso 1 1 calc R . .
H6B H 0.3858 0.6208 0.4363 0.024 Uiso 1 1 calc R . .
C7 C 0.4016(2) 0.8228(2) 0.40683(10) 0.0185(5) Uani 1 1 d . . .
C8 C 0.3001(2) 0.8376(3) 0.36694(11) 0.0203(6) Uani 1 1 d . . .
C9 C 0.2570(2) 0.9678(3) 0.34793(11) 0.0224(6) Uani 1 1 d . . .
C10 C 0.3147(2) 1.0881(3) 0.36931(11) 0.0214(6) Uani 1 1 d . . .
C11 C 0.4156(2) 1.0774(2) 0.40840(10) 0.0198(5) Uani 1 1 d . . .
C12 C 0.4587(2) 0.9460(2) 0.42604(10) 0.0174(5) Uani 1 1 d . . .
F8A F -0.01225(13) 0.77810(15) 0.29718(6) 0.0296(4) Uani 1 1 d . . .
F9A F 0.08518(14) 0.59735(17) 0.23040(6) 0.0349(4) Uani 1 1 d . . .
F10A F 0.09259(14) 0.31670(17) 0.25454(7) 0.0364(4) Uani 1 1 d . . .
F11A F 0.01085(15) 0.22146(16) 0.34889(7) 0.0389(4) Uani 1 1 d . . .
F12A F -0.07396(15) 0.40497(17) 0.41930(7) 0.0356(4) Uani 1 1 d . . .
N1A N 0.00452(18) 0.7950(2) 0.42797(8) 0.0207(5) Uani 1 1 d . . .
N2A N 0.2693(2) 0.7472(3) 0.53125(10) 0.0300(5) Uani 1 1 d D . .
H2C H 0.274(3) 0.6531(19) 0.5331(13) 0.036 Uiso 1 1 d D . .
H2D H 0.305(2) 0.795(3) 0.5620(9) 0.036 Uiso 1 1 d D . .
C1A C 0.0905(2) 0.7315(3) 0.46448(10) 0.0218(6) Uani 1 1 d . . .
H1A H 0.0903 0.6318 0.4686 0.026 Uiso 1 1 calc R . .
C2A C 0.1803(2) 0.8118(3) 0.49652(10) 0.0234(6) Uani 1 1 d . . .
C3A C 0.1749(2) 0.9590(3) 0.48951(11) 0.0249(6) Uani 1 1 d . . .
H3A H 0.2324 1.0173 0.5114 0.030 Uiso 1 1 calc R . .
C4A C 0.0871(2) 1.0188(3) 0.45118(11) 0.0259(6) Uani 1 1 d . . .
H4A H 0.0854 1.1183 0.4460 0.031 Uiso 1 1 calc R . .
C5A C 0.0009(2) 0.9360(3) 0.41987(11) 0.0233(6) Uani 1 1 d . . .
H5A H -0.0596 0.9776 0.3932 0.028 Uiso 1 1 calc R . .
C6A C -0.0925(2) 0.7046(3) 0.39811(11) 0.0231(6) Uani 1 1 d . . .
H6A1 H -0.1521 0.7649 0.3748 0.028 Uiso 1 1 calc R . .
H6A2 H -0.1322 0.6549 0.4266 0.028 Uiso 1 1 calc R . .
C7A C -0.0450(2) 0.5977(3) 0.36030(10) 0.0205(5) Uani 1 1 d . . .
C8A C -0.0054(2) 0.6407(3) 0.31109(10) 0.0209(6) Uani 1 1 d . . .
C9A C 0.0425(2) 0.5490(3) 0.27611(11) 0.0255(6) Uani 1 1 d . . .
C10A C 0.0476(2) 0.4074(3) 0.28895(11) 0.0255(6) Uani 1 1 d . . .
C11A C 0.0068(2) 0.3597(3) 0.33680(11) 0.0259(6) Uani 1 1 d . . .
C12A C -0.0379(2) 0.4550(3) 0.37213(11) 0.0240(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02834(16) 0.02998(16) 0.03033(16) 0.00292(12) 0.01088(12) 0.00291(12)
Br2 0.02638(15) 0.02163(14) 0.02407(14) -0.00109(10) 0.00577(11) 0.00086(11)
F8 0.0273(9) 0.0235(8) 0.0412(10) -0.0049(7) -0.0037(7) -0.0066(7)
F9 0.0296(9) 0.0349(9) 0.0363(9) 0.0022(7) -0.0082(8) 0.0015(7)
F10 0.0310(9) 0.0233(8) 0.0336(9) 0.0077(7) 0.0064(7) 0.0071(7)
F11 0.0289(9) 0.0160(7) 0.0366(9) -0.0027(6) 0.0045(7) -0.0034(6)
F12 0.0197(8) 0.0237(8) 0.0260(8) -0.0020(6) -0.0010(6) -0.0008(6)
N1 0.0205(11) 0.0159(11) 0.0197(11) -0.0004(9) 0.0027(9) 0.0002(9)
N2 0.0282(13) 0.0258(12) 0.0289(13) -0.0082(10) 0.0134(11) -0.0024(10)
C1 0.0178(13) 0.0168(12) 0.0249(14) -0.0023(10) 0.0040(11) -0.0032(10)
C2 0.0184(13) 0.0238(14) 0.0207(13) 0.0003(11) 0.0009(11) 0.0015(11)
C3 0.0400(18) 0.0251(15) 0.0329(16) -0.0105(12) 0.0129(14) -0.0007(13)
C4 0.061(2) 0.0170(14) 0.0448(19) -0.0073(13) 0.0238(17) -0.0046(14)
C5 0.0419(18) 0.0177(14) 0.0338(16) -0.0024(12) 0.0106(14) -0.0084(12)
C6 0.0215(14) 0.0195(13) 0.0209(13) -0.0003(10) 0.0078(11) 0.0009(10)
C7 0.0199(13) 0.0201(13) 0.0181(13) 0.0003(10) 0.0112(11) -0.0005(10)
C8 0.0177(13) 0.0207(13) 0.0233(14) -0.0052(11) 0.0058(11) -0.0064(10)
C9 0.0153(13) 0.0294(15) 0.0225(14) 0.0026(11) 0.0033(11) 0.0010(11)
C10 0.0228(14) 0.0202(13) 0.0233(14) 0.0034(11) 0.0102(11) 0.0035(11)
C11 0.0226(14) 0.0160(12) 0.0222(13) -0.0036(10) 0.0081(11) -0.0029(10)
C12 0.0133(12) 0.0237(13) 0.0165(12) 0.0000(10) 0.0060(10) 0.0010(10)
F8A 0.0340(9) 0.0282(8) 0.0274(8) 0.0048(7) 0.0079(7) -0.0023(7)
F9A 0.0381(10) 0.0461(10) 0.0238(8) 0.0036(7) 0.0154(7) -0.0008(8)
F10A 0.0376(10) 0.0405(10) 0.0318(9) -0.0104(7) 0.0076(8) 0.0051(8)
F11A 0.0428(10) 0.0264(9) 0.0475(11) 0.0050(8) 0.0077(9) 0.0001(7)
F12A 0.0411(10) 0.0400(9) 0.0288(9) 0.0120(7) 0.0151(8) -0.0015(8)
N1A 0.0193(11) 0.0285(12) 0.0152(10) -0.0013(9) 0.0052(9) 0.0002(9)
N2A 0.0268(14) 0.0348(14) 0.0266(13) -0.0014(11) -0.0017(11) -0.0002(11)
C1A 0.0206(14) 0.0270(14) 0.0185(13) 0.0015(11) 0.0055(11) -0.0006(11)
C2A 0.0179(13) 0.0374(16) 0.0165(13) 0.0008(11) 0.0075(11) -0.0022(12)
C3A 0.0216(14) 0.0326(15) 0.0220(14) -0.0049(12) 0.0081(11) -0.0057(12)
C4A 0.0281(15) 0.0305(15) 0.0219(14) -0.0023(12) 0.0131(12) -0.0028(12)
C5A 0.0242(15) 0.0287(15) 0.0184(13) 0.0007(11) 0.0080(11) 0.0051(11)
C6A 0.0175(14) 0.0319(15) 0.0195(13) -0.0008(11) 0.0021(11) -0.0003(11)
C7A 0.0138(13) 0.0285(14) 0.0183(13) 0.0001(11) -0.0004(10) -0.0026(11)
C8A 0.0198(14) 0.0244(14) 0.0178(13) 0.0009(10) 0.0009(11) -0.0051(11)
C9A 0.0186(14) 0.0418(17) 0.0164(13) 0.0003(12) 0.0036(11) -0.0039(12)
C10A 0.0215(14) 0.0319(15) 0.0224(14) -0.0074(12) 0.0006(11) -0.0003(12)
C11A 0.0244(15) 0.0261(15) 0.0259(14) 0.0028(11) 0.0000(12) -0.0029(11)
C12A 0.0172(13) 0.0345(15) 0.0208(13) 0.0041(12) 0.0045(11) -0.0018(11)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F8 C8 1.346(3) . ?
F9 C9 1.339(3) . ?
F10 C10 1.337(3) . ?
F11 C11 1.338(3) . ?
F12 C12 1.340(3) . ?
N1 C5 1.337(3) . ?
N1 C1 1.343(3) . ?
N1 C6 1.499(3) . ?
N2 C2 1.352(3) . ?
N2 H2A 0.890(17) . ?
N2 H2B 0.864(17) . ?
C1 C2 1.396(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.398(4) . ?
C3 C4 1.375(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.501(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.381(3) . ?
C7 C8 1.388(3) . ?
C8 C9 1.379(3) . ?
C9 C10 1.375(4) . ?
C10 C11 1.369(4) . ?
C11 C12 1.381(3) . ?
F8A C8A 1.343(3) . ?
F9A C9A 1.340(3) . ?
F10A C10A 1.343(3) . ?
F11A C11A 1.340(3) . ?
F12A C12A 1.340(3) . ?
N1A C1A 1.349(3) . ?
N1A C5A 1.349(3) . ?
N1A C6A 1.492(3) . ?
N2A C2A 1.354(3) . ?
N2A H2C 0.893(17) . ?
N2A H2D 0.905(17) . ?
C1A C2A 1.404(3) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.405(4) . ?
C3A C4A 1.370(4) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.384(4) . ?
C4A H4A 0.9500 . ?
C5A H5A 0.9500 . ?
C6A C7A 1.510(3) . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C7A C8A 1.380(3) . ?
C7A C12A 1.381(4) . ?
C8A C9A 1.373(4) . ?
C9A C10A 1.376(4) . ?
C10A C11A 1.371(4) . ?
C11A C12A 1.384(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 122.8(2) . . ?
C5 N1 C6 118.2(2) . . ?
C1 N1 C6 118.98(19) . . ?
C2 N2 H2A 120.1(19) . . ?
C2 N2 H2B 117.9(19) . . ?
H2A N2 H2B 121(3) . . ?
N1 C1 C2 120.9(2) . . ?
N1 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
N2 C2 C1 120.2(2) . . ?
N2 C2 C3 122.9(2) . . ?
C1 C2 C3 116.8(2) . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
N1 C5 C4 118.4(3) . . ?
N1 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
N1 C6 C7 110.96(19) . . ?
N1 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C12 C7 C8 116.3(2) . . ?
C12 C7 C6 121.4(2) . . ?
C8 C7 C6 122.3(2) . . ?
F8 C8 C9 119.1(2) . . ?
F8 C8 C7 118.7(2) . . ?
C9 C8 C7 122.3(2) . . ?
F9 C9 C10 119.6(2) . . ?
F9 C9 C8 120.8(2) . . ?
C10 C9 C8 119.6(2) . . ?
F10 C10 C11 120.1(2) . . ?
F10 C10 C9 120.0(2) . . ?
C11 C10 C9 119.8(2) . . ?
F11 C11 C10 120.6(2) . . ?
F11 C11 C12 119.5(2) . . ?
C10 C11 C12 119.8(2) . . ?
F12 C12 C11 118.3(2) . . ?
F12 C12 C7 119.4(2) . . ?
C11 C12 C7 122.3(2) . . ?
C1A N1A C5A 122.5(2) . . ?
C1A N1A C6A 117.7(2) . . ?
C5A N1A C6A 119.7(2) . . ?
C2A N2A H2C 121.0(19) . . ?
C2A N2A H2D 118.1(19) . . ?
H2C N2A H2D 116(3) . . ?
N1A C1A C2A 120.5(2) . . ?
N1A C1A H1A 119.8 . . ?
C2A C1A H1A 119.8 . . ?
N2A C2A C1A 120.3(2) . . ?
N2A C2A C3A 122.4(2) . . ?
C1A C2A C3A 117.3(2) . . ?
C4A C3A C2A 120.2(2) . . ?
C4A C3A H3A 119.9 . . ?
C2A C3A H3A 119.9 . . ?
C3A C4A C5A 120.8(3) . . ?
C3A C4A H4A 119.6 . . ?
C5A C4A H4A 119.6 . . ?
N1A C5A C4A 118.7(2) . . ?
N1A C5A H5A 120.6 . . ?
C4A C5A H5A 120.6 . . ?
N1A C6A C7A 111.1(2) . . ?
N1A C6A H6A1 109.4 . . ?
C7A C6A H6A1 109.4 . . ?
N1A C6A H6A2 109.4 . . ?
C7A C6A H6A2 109.4 . . ?
H6A1 C6A H6A2 108.0 . . ?
C8A C7A C12A 116.4(2) . . ?
C8A C7A C6A 120.2(2) . . ?
C12A C7A C6A 123.4(2) . . ?
F8A C8A C9A 118.5(2) . . ?
F8A C8A C7A 118.7(2) . . ?
C9A C8A C7A 122.8(2) . . ?
F9A C9A C8A 120.3(2) . . ?
F9A C9A C10A 120.4(2) . . ?
C8A C9A C10A 119.3(2) . . ?
F10A C10A C11A 120.5(2) . . ?
F10A C10A C9A 119.7(2) . . ?
C11A C10A C9A 119.8(2) . . ?
F11A C11A C10A 119.7(2) . . ?
F11A C11A C12A 120.7(2) . . ?
C10A C11A C12A 119.6(2) . . ?
F12A C12A C7A 120.1(2) . . ?
F12A C12A C11A 117.9(2) . . ?
C7A C12A C11A 122.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 2.2(4) . . . . ?
C6 N1 C1 C2 179.8(2) . . . . ?
N1 C1 C2 N2 177.5(2) . . . . ?
N1 C1 C2 C3 -3.1(4) . . . . ?
N2 C2 C3 C4 -179.1(3) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
C2 C3 C4 C5 1.1(5) . . . . ?
C1 N1 C5 C4 0.5(4) . . . . ?
C6 N1 C5 C4 -177.1(3) . . . . ?
C3 C4 C5 N1 -2.2(5) . . . . ?
C5 N1 C6 C7 -138.9(2) . . . . ?
C1 N1 C6 C7 43.4(3) . . . . ?
N1 C6 C7 C12 -104.5(3) . . . . ?
N1 C6 C7 C8 72.7(3) . . . . ?
C12 C7 C8 F8 177.7(2) . . . . ?
C6 C7 C8 F8 0.4(3) . . . . ?
C12 C7 C8 C9 -0.9(4) . . . . ?
C6 C7 C8 C9 -178.2(2) . . . . ?
F8 C8 C9 F9 -1.3(4) . . . . ?
C7 C8 C9 F9 177.3(2) . . . . ?
F8 C8 C9 C10 -179.4(2) . . . . ?
C7 C8 C9 C10 -0.8(4) . . . . ?
F9 C9 C10 F10 0.1(4) . . . . ?
C8 C9 C10 F10 178.2(2) . . . . ?
F9 C9 C10 C11 -176.8(2) . . . . ?
C8 C9 C10 C11 1.2(4) . . . . ?
F10 C10 C11 F11 0.7(4) . . . . ?
C9 C10 C11 F11 177.7(2) . . . . ?
F10 C10 C11 C12 -176.9(2) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
F11 C11 C12 F12 -0.9(3) . . . . ?
C10 C11 C12 F12 176.8(2) . . . . ?
F11 C11 C12 C7 -179.6(2) . . . . ?
C10 C11 C12 C7 -1.9(4) . . . . ?
C8 C7 C12 F12 -176.4(2) . . . . ?
C6 C7 C12 F12 0.9(3) . . . . ?
C8 C7 C12 C11 2.3(3) . . . . ?
C6 C7 C12 C11 179.6(2) . . . . ?
C5A N1A C1A C2A 0.8(4) . . . . ?
C6A N1A C1A C2A -176.1(2) . . . . ?
N1A C1A C2A N2A -177.1(2) . . . . ?
N1A C1A C2A C3A 1.1(4) . . . . ?
N2A C2A C3A C4A 175.9(2) . . . . ?
C1A C2A C3A C4A -2.3(4) . . . . ?
C2A C3A C4A C5A 1.6(4) . . . . ?
C1A N1A C5A C4A -1.5(4) . . . . ?
C6A N1A C5A C4A 175.3(2) . . . . ?
C3A C4A C5A N1A 0.3(4) . . . . ?
C1A N1A C6A C7A -62.9(3) . . . . ?
C5A N1A C6A C7A 120.1(2) . . . . ?
N1A C6A C7A C8A -71.0(3) . . . . ?
N1A C6A C7A C12A 108.8(3) . . . . ?
C12A C7A C8A F8A 178.9(2) . . . . ?
C6A C7A C8A F8A -1.3(3) . . . . ?
C12A C7A C8A C9A -2.1(4) . . . . ?
C6A C7A C8A C9A 177.7(2) . . . . ?
F8A C8A C9A F9A 2.5(4) . . . . ?
C7A C8A C9A F9A -176.5(2) . . . . ?
F8A C8A C9A C10A -178.5(2) . . . . ?
C7A C8A C9A C10A 2.6(4) . . . . ?
F9A C9A C10A F10A -1.9(4) . . . . ?
C8A C9A C10A F10A 179.0(2) . . . . ?
F9A C9A C10A C11A 178.1(2) . . . . ?
C8A C9A C10A C11A -1.0(4) . . . . ?
F10A C10A C11A F11A -0.7(4) . . . . ?
C9A C10A C11A F11A 179.4(2) . . . . ?
F10A C10A C11A C12A 179.2(2) . . . . ?
C9A C10A C11A C12A -0.8(4) . . . . ?
C8A C7A C12A F12A 179.6(2) . . . . ?
C6A C7A C12A F12A -0.2(4) . . . . ?
C8A C7A C12A C11A 0.2(4) . . . . ?
C6A C7A C12A C11A -179.6(2) . . . . ?
F11A C11A C12A F12A 1.7(4) . . . . ?
C10A C11A C12A F12A -178.2(2) . . . . ?
F11A C11A C12A C7A -179.0(2) . . . . ?
C10A C11A C12A C7A 1.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A Br2 0.890(17) 2.625(19) 3.468(2) 159(2) 2_655
N2 H2B Br2 0.864(17) 2.636(18) 3.500(2) 178(3) .
N2A H2C Br1 0.893(17) 2.71(2) 3.524(2) 152(2) .
N2A H2D Br2 0.905(17) 2.88(2) 3.701(2) 151(2) 4_576

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.064

_iucr_refine_instructions_details 
;
TITL mm-md-22-1 in P 21/n
CELL   0.71073  11.4302   9.4748  23.7921  90.000  98.854  90.000
ZERR     8       0.0002   0.0001   0.0005   0.000   0.001   0.000
LATT  1
SYMM 1/2-X,1/2+Y,1/2-Z
SFAC        C       H       N       F       BR
UNIT        96      64      16      40       8
L.S.      10
OMIT -3 50.5
OMIT 0 0 2
OMIT 0 1 1
OMIT 5 2 4
TEMP  -150
SIZE  0.52 0.09 0.07
EQIV $1 -x+3/2, y+1/2, -z+1/2
EQIV $2 x-1/2, -y+3/2, z+1/2
HTAB N2 Br2_$1
HTAB N2 Br2
HTAB N2A Br1
HTAB N2A Br2_$2
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.010700    2.612000
FVAR       0.31614
BR1   5    0.253244    0.393358    0.485077    11.00000    0.02834    0.02998 =
         0.03033    0.00292    0.01088    0.00291
BR2   5    0.795853    0.539501    0.162898    11.00000    0.02638    0.02163 =
         0.02407   -0.00109    0.00577    0.00086
MOLE 1
F8    4    0.243505    0.720505    0.345359    11.00000    0.02730    0.02355 =
         0.04120   -0.00486   -0.00373   -0.00663
F9    4    0.161582    0.978332    0.307740    11.00000    0.02964    0.03488 =
         0.03631    0.00223   -0.00816    0.00155
F10   4    0.275454    1.214751    0.350072    11.00000    0.03104    0.02334 =
         0.03364    0.00772    0.00637    0.00706
F11   4    0.475187    1.193128    0.428251    11.00000    0.02888    0.01603 =
         0.03665   -0.00273    0.00449   -0.00345
F12   4    0.560701    0.938962    0.462213    11.00000    0.01966    0.02375 =
         0.02602   -0.00202   -0.00099   -0.00085
N1    3    0.506397    0.610045    0.380767    11.00000    0.02052    0.01587 =
         0.01968   -0.00035    0.00273    0.00016
N2    3    0.695914    0.703918    0.278397    11.00000    0.02816    0.02575 =
         0.02890   -0.00820    0.01336   -0.00245
H2A   2    0.700544    0.796875    0.283600    11.00000   -1.20000
H2B   2    0.720159    0.665373    0.249336    11.00000   -1.20000
DFIX 0.91 N2 H2A N2 H2B
C1    1    0.575768    0.686369    0.351541    11.00000    0.01776    0.01683 =
         0.02490   -0.00227    0.00395   -0.00320
AFIX  43
H1    2    0.588078    0.783730    0.359995    11.00000   -1.20000
AFIX   0
C2    1    0.630027    0.624575    0.308911    11.00000    0.01843    0.02382 =
         0.02070    0.00026    0.00091    0.00150
C3    1    0.613318    0.479521    0.300386    11.00000    0.04002    0.02510 =
         0.03291   -0.01052    0.01290   -0.00069
AFIX  43
H3    2    0.650040    0.432454    0.272456    11.00000   -1.20000
AFIX   0
C4    1    0.543979    0.404685    0.332241    11.00000    0.06077    0.01702 =
         0.04475   -0.00731    0.02375   -0.00457
AFIX  43
H4    2    0.534319    0.305852    0.326605    11.00000   -1.20000
AFIX   0
C5    1    0.488175    0.471783    0.372387    11.00000    0.04191    0.01775 =
         0.03382   -0.00241    0.01056   -0.00843
AFIX  43
H5    2    0.438066    0.420834    0.393519    11.00000   -1.20000
AFIX   0
C6    1    0.450451    0.680905    0.426306    11.00000    0.02152    0.01954 =
         0.02086   -0.00032    0.00782    0.00086
AFIX  23
H6A   2    0.510182    0.692515    0.460824    11.00000   -1.20000
H6B   2    0.385824    0.620826    0.436286    11.00000   -1.20000
AFIX   0
C7    1    0.401579    0.822775    0.406827    11.00000    0.01991    0.02006 =
         0.01814    0.00027    0.01120   -0.00051
C8    1    0.300085    0.837590    0.366945    11.00000    0.01773    0.02069 =
         0.02327   -0.00520    0.00578   -0.00640
C9    1    0.256953    0.967819    0.347931    11.00000    0.01527    0.02942 =
         0.02251    0.00256    0.00330    0.00095
C10   1    0.314703    1.088083    0.369313    11.00000    0.02278    0.02025 =
         0.02330    0.00342    0.01021    0.00350
C11   1    0.415558    1.077421    0.408398    11.00000    0.02264    0.01600 =
         0.02222   -0.00355    0.00806   -0.00293
C12   1    0.458672    0.946002    0.426041    11.00000    0.01328    0.02373 =
         0.01646   -0.00002    0.00600    0.00103
MOLE 2
F8A   4   -0.012250    0.778098    0.297178    11.00000    0.03401    0.02824 =
         0.02741    0.00480    0.00791   -0.00234
F9A   4    0.085183    0.597354    0.230401    11.00000    0.03806    0.04611 =
         0.02380    0.00355    0.01544   -0.00079
F10A  4    0.092588    0.316704    0.254536    11.00000    0.03763    0.04048 =
         0.03183   -0.01041    0.00757    0.00511
F11A  4    0.010846    0.221455    0.348889    11.00000    0.04282    0.02644 =
         0.04754    0.00501    0.00769    0.00015
F12A  4   -0.073964    0.404971    0.419298    11.00000    0.04113    0.03998 =
         0.02880    0.01197    0.01505   -0.00147
N1A   3    0.004519    0.795026    0.427965    11.00000    0.01925    0.02854 =
         0.01517   -0.00125    0.00520    0.00019
N2A   3    0.269267    0.747187    0.531253    11.00000    0.02681    0.03483 =
         0.02665   -0.00145   -0.00173   -0.00021
H2C   2    0.274018    0.653139    0.533073    11.00000   -1.20000
H2D   2    0.305155    0.795205    0.562020    11.00000   -1.20000
DFIX 0.91 N2A H2C N2A H2D
C1A   1    0.090485    0.731547    0.464481    11.00000    0.02060    0.02698 =
         0.01853    0.00153    0.00547   -0.00058
AFIX  43
H1A   2    0.090279    0.631808    0.468555    11.00000   -1.20000
AFIX   0
C2A   1    0.180297    0.811805    0.496524    11.00000    0.01789    0.03741 =
         0.01649    0.00084    0.00747   -0.00223
C3A   1    0.174928    0.959023    0.489508    11.00000    0.02158    0.03260 =
         0.02204   -0.00491    0.00811   -0.00571
AFIX  43
H3A   2    0.232366    1.017322    0.511417    11.00000   -1.20000
AFIX   0
C4A   1    0.087141    1.018813    0.451179    11.00000    0.02806    0.03053 =
         0.02195   -0.00226    0.01308   -0.00283
AFIX  43
H4A   2    0.085432    1.118263    0.446035    11.00000   -1.20000
AFIX   0
C5A   1    0.000917    0.935974    0.419867    11.00000    0.02420    0.02865 =
         0.01841    0.00068    0.00797    0.00508
AFIX  43
H5A   2   -0.059644    0.977596    0.393182    11.00000   -1.20000
AFIX   0
C6A   1   -0.092530    0.704645    0.398111    11.00000    0.01754    0.03185 =
         0.01952   -0.00075    0.00206   -0.00033
AFIX  23
H6A1  2   -0.152096    0.764865    0.374818    11.00000   -1.20000
H6A2  2   -0.132164    0.654910    0.426568    11.00000   -1.20000
AFIX   0
C7A   1   -0.044988    0.597745    0.360303    11.00000    0.01385    0.02854 =
         0.01831    0.00012   -0.00045   -0.00257
C8A   1   -0.005409    0.640653    0.311094    11.00000    0.01977    0.02442 =
         0.01783    0.00094    0.00090   -0.00512
C9A   1    0.042454    0.549037    0.276110    11.00000    0.01861    0.04181 =
         0.01643    0.00029    0.00362   -0.00392
C10A  1    0.047585    0.407355    0.288951    11.00000    0.02152    0.03187 =
         0.02238   -0.00745    0.00064   -0.00026
C11A  1    0.006777    0.359696    0.336797    11.00000    0.02438    0.02612 =
         0.02587    0.00284   -0.00003   -0.00293
C12A  1   -0.037928    0.454995    0.372125    11.00000    0.01719    0.03446 =
         0.02078    0.00405    0.00452   -0.00179
 
HKLF   4
 
REM  mm-md-22-1 in P 21/n
REM R1 =  0.0271 for   3867 Fo > 4sig(Fo)  and  0.0386 for all   4612 data
REM    373 parameters refined using      4 restraints
 
END
 
WGHT      0.0107      2.6063
REM Highest difference peak  0.278,  deepest hole -0.281,  1-sigma level  0.064
Q1    1   0.3393  0.8924  0.3089  11.00000  0.05    0.28
Q2    1  -0.0319  0.5349  0.3646  11.00000  0.05    0.28
Q3    1   0.6023  0.5640  0.3049  11.00000  0.05    0.27
Q4    1   0.2566  0.5163  0.4931  11.00000  0.05    0.26
Q5    1   0.6758  0.6467  0.3014  11.00000  0.05    0.26
Q6    1   0.0218  0.4203  0.3639  11.00000  0.05    0.26
Q7    1   0.0729  1.1480  0.4482  11.00000  0.05    0.26
Q8    1   0.8950  0.6283  0.1553  11.00000  0.05    0.25
Q9    1   0.0084  0.5782  0.2899  11.00000  0.05    0.25
Q10   1   0.4186  1.0043  0.4221  11.00000  0.05    0.24
Q11   1   0.2822  1.0292  0.3640  11.00000  0.05    0.24
Q12   1   0.0434  0.7851  0.4566  11.00000  0.05    0.24
Q13   1   0.2620  0.9095  0.3646  11.00000  0.05    0.24
Q14   1   0.3584  0.4234  0.4359  11.00000  0.05    0.24
Q15   1   0.0354  0.4801  0.2822  11.00000  0.05    0.23
Q16   1   0.5938  0.6627  0.3214  11.00000  0.05    0.23
Q17   1   0.0820  0.4017  0.3296  11.00000  0.05    0.22
Q18   1   0.1958  0.9663  0.3654  11.00000  0.05    0.22
Q19   1   0.5341  0.6563  0.4458  11.00000  0.05    0.22
Q20   1   0.4797  0.6509  0.4024  11.00000  0.05    0.22
Q21   1   0.9000  0.4775  0.1562  11.00000  0.05    0.22
Q22   1  -0.1466  0.9680  0.3376  11.00000  0.05    0.22
Q23   1   0.8101  0.6769  0.1668  11.00000  0.05    0.22
Q24   1   0.0072  0.8636  0.4227  11.00000  0.05    0.21
Q25   1  -0.0615  0.6450  0.3765  11.00000  0.05    0.21
;
_database_code_depnum_ccdc_archive 'CCDC 1005287'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-js-28

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H17 F5 N, I'
_chemical_formula_sum            'C13 H17 F5 I N'
_chemical_formula_weight         409.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.01450(10)
_cell_length_b                   13.8741(2)
_cell_length_c                   13.5995(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.0150(10)
_cell_angle_gamma                90.00
_cell_volume                     1506.39(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3824
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    2.169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4102
_exptl_absorpt_correction_T_max  0.6834
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8756
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2656
_reflns_number_gt                2480
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0117P)^2^+1.3846P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2656
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0189
_refine_ls_wR_factor_ref         0.0435
_refine_ls_wR_factor_gt          0.0427
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.289246(19) 0.338101(10) 0.142821(10) 0.02189(6) Uani 1 1 d . . .
F9 F 0.33351(17) 0.19233(10) -0.16909(10) 0.0314(3) Uani 1 1 d . . .
F10 F 0.11027(18) 0.09366(11) -0.07249(14) 0.0457(4) Uani 1 1 d . . .
F11 F 0.2020(2) 0.01591(10) 0.10705(12) 0.0444(4) Uani 1 1 d . . .
F12 F 0.5217(2) 0.03491(10) 0.18826(10) 0.0391(4) Uani 1 1 d . . .
F13 F 0.74745(18) 0.12986(10) 0.09169(10) 0.0300(3) Uani 1 1 d . . .
N1 N 0.6996(2) 0.32676(12) -0.07488(13) 0.0149(4) Uani 1 1 d . . .
C1 C 0.7514(3) 0.33907(15) 0.03495(15) 0.0176(5) Uani 1 1 d . . .
H1A H 0.6544 0.3227 0.0721 0.021 Uiso 1 1 calc R . .
H1B H 0.8413 0.2920 0.0542 0.021 Uiso 1 1 calc R . .
C2 C 0.8129(3) 0.43870(16) 0.06656(16) 0.0222(5) Uani 1 1 d . . .
H2A H 0.8426 0.4393 0.1380 0.033 Uiso 1 1 calc R . .
H2B H 0.7241 0.4860 0.0498 0.033 Uiso 1 1 calc R . .
H2C H 0.9117 0.4552 0.0323 0.033 Uiso 1 1 calc R . .
C3 C 0.8325(3) 0.36501(16) -0.13865(16) 0.0173(5) Uani 1 1 d . . .
H3A H 0.7939 0.3536 -0.2088 0.021 Uiso 1 1 calc R . .
H3B H 0.8420 0.4356 -0.1290 0.021 Uiso 1 1 calc R . .
C4 C 1.0043(3) 0.32094(16) -0.11797(17) 0.0221(5) Uani 1 1 d . . .
H4A H 1.0811 0.3496 -0.1620 0.033 Uiso 1 1 calc R . .
H4B H 0.9975 0.2512 -0.1293 0.033 Uiso 1 1 calc R . .
H4C H 1.0457 0.3334 -0.0492 0.033 Uiso 1 1 calc R . .
C5 C 0.5382(3) 0.38274(15) -0.09977(15) 0.0169(4) Uani 1 1 d . . .
H5A H 0.4479 0.3516 -0.0660 0.020 Uiso 1 1 calc R . .
H5B H 0.5532 0.4487 -0.0726 0.020 Uiso 1 1 calc R . .
C6 C 0.4816(3) 0.39050(17) -0.20893(16) 0.0222(5) Uani 1 1 d . . .
H6A H 0.3769 0.4273 -0.2175 0.033 Uiso 1 1 calc R . .
H6B H 0.4632 0.3258 -0.2367 0.033 Uiso 1 1 calc R . .
H6C H 0.5680 0.4234 -0.2431 0.033 Uiso 1 1 calc R . .
C7 C 0.6757(3) 0.21951(14) -0.09664(15) 0.0163(4) Uani 1 1 d . . .
H7A H 0.6433 0.2116 -0.1681 0.020 Uiso 1 1 calc R . .
H7B H 0.7846 0.1866 -0.0817 0.020 Uiso 1 1 calc R . .
C8 C 0.5465(3) 0.16989(14) -0.04004(16) 0.0172(5) Uani 1 1 d . . .
C9 C 0.3832(3) 0.15661(15) -0.07933(18) 0.0214(5) Uani 1 1 d . . .
C10 C 0.2666(3) 0.10601(16) -0.0308(2) 0.0284(6) Uani 1 1 d . . .
C11 C 0.3131(3) 0.06646(16) 0.05979(19) 0.0288(6) Uani 1 1 d . . .
C12 C 0.4743(3) 0.07639(16) 0.10085(17) 0.0264(5) Uani 1 1 d . . .
C13 C 0.5886(3) 0.12663(16) 0.05099(16) 0.0209(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.02840(10) 0.02021(9) 0.01774(9) 0.00252(5) 0.00597(6) 0.00296(6)
F9 0.0264(8) 0.0265(7) 0.0389(8) 0.0106(6) -0.0107(6) -0.0042(6)
F10 0.0187(8) 0.0293(8) 0.0884(13) 0.0139(8) 0.0010(8) -0.0057(6)
F11 0.0519(10) 0.0265(8) 0.0608(10) -0.0006(7) 0.0392(8) -0.0102(7)
F12 0.0749(12) 0.0258(8) 0.0179(7) 0.0034(6) 0.0108(7) -0.0097(8)
F13 0.0377(9) 0.0249(7) 0.0252(7) 0.0055(6) -0.0099(6) -0.0061(6)
N1 0.0156(9) 0.0139(9) 0.0155(9) 0.0004(7) 0.0022(7) 0.0002(7)
C1 0.0214(12) 0.0176(11) 0.0135(10) 0.0001(8) -0.0001(9) -0.0008(9)
C2 0.0270(13) 0.0190(12) 0.0205(11) -0.0036(9) 0.0012(9) -0.0017(10)
C3 0.0172(12) 0.0176(11) 0.0179(11) 0.0018(9) 0.0056(9) -0.0026(9)
C4 0.0186(12) 0.0230(12) 0.0252(12) 0.0017(9) 0.0045(9) 0.0008(9)
C5 0.0151(11) 0.0145(11) 0.0214(11) 0.0006(9) 0.0032(9) 0.0044(9)
C6 0.0203(12) 0.0237(12) 0.0221(12) 0.0027(9) 0.0001(9) 0.0030(10)
C7 0.0189(11) 0.0136(11) 0.0166(10) -0.0014(8) 0.0022(9) 0.0004(9)
C8 0.0222(12) 0.0123(11) 0.0176(11) -0.0018(8) 0.0045(9) 0.0004(9)
C9 0.0238(12) 0.0134(11) 0.0270(12) 0.0011(9) 0.0022(10) 0.0019(9)
C10 0.0207(13) 0.0150(12) 0.0504(16) -0.0026(11) 0.0081(11) 0.0013(10)
C11 0.0361(15) 0.0129(11) 0.0408(15) -0.0033(10) 0.0238(12) -0.0044(10)
C12 0.0474(16) 0.0145(11) 0.0190(12) -0.0031(9) 0.0120(11) -0.0026(11)
C13 0.0286(13) 0.0142(11) 0.0202(11) -0.0024(9) 0.0026(10) 0.0014(10)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F9 C9 1.345(3) . ?
F10 C10 1.341(3) . ?
F11 C11 1.341(3) . ?
F12 C12 1.345(3) . ?
F13 C13 1.344(3) . ?
N1 C5 1.521(3) . ?
N1 C1 1.524(3) . ?
N1 C7 1.526(3) . ?
N1 C3 1.526(3) . ?
C1 C2 1.517(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.510(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.518(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.509(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.382(3) . ?
C8 C13 1.391(3) . ?
C9 C10 1.382(3) . ?
C10 C11 1.370(4) . ?
C11 C12 1.369(4) . ?
C12 C13 1.376(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 108.31(16) . . ?
C5 N1 C7 111.39(16) . . ?
C1 N1 C7 108.54(15) . . ?
C5 N1 C3 108.54(15) . . ?
C1 N1 C3 111.97(16) . . ?
C7 N1 C3 108.11(15) . . ?
C2 C1 N1 115.69(17) . . ?
C2 C1 H1A 108.4 . . ?
N1 C1 H1A 108.4 . . ?
C2 C1 H1B 108.4 . . ?
N1 C1 H1B 108.4 . . ?
H1A C1 H1B 107.4 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 N1 115.05(17) . . ?
C4 C3 H3A 108.5 . . ?
N1 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
N1 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N1 115.45(17) . . ?
C6 C5 H5A 108.4 . . ?
N1 C5 H5A 108.4 . . ?
C6 C5 H5B 108.4 . . ?
N1 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N1 115.21(16) . . ?
C8 C7 H7A 108.5 . . ?
N1 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
N1 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C13 115.8(2) . . ?
C9 C8 C7 122.2(2) . . ?
C13 C8 C7 121.8(2) . . ?
F9 C9 C10 117.5(2) . . ?
F9 C9 C8 119.8(2) . . ?
C10 C9 C8 122.7(2) . . ?
F10 C10 C11 120.0(2) . . ?
F10 C10 C9 120.6(2) . . ?
C11 C10 C9 119.4(2) . . ?
F11 C11 C12 120.0(2) . . ?
F11 C11 C10 120.1(2) . . ?
C12 C11 C10 119.9(2) . . ?
F12 C12 C11 120.1(2) . . ?
F12 C12 C13 120.2(2) . . ?
C11 C12 C13 119.7(2) . . ?
F13 C13 C12 117.5(2) . . ?
F13 C13 C8 120.0(2) . . ?
C12 C13 C8 122.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -70.2(2) . . . . ?
C7 N1 C1 C2 168.71(18) . . . . ?
C3 N1 C1 C2 49.4(2) . . . . ?
C5 N1 C3 C4 176.22(18) . . . . ?
C1 N1 C3 C4 56.7(2) . . . . ?
C7 N1 C3 C4 -62.8(2) . . . . ?
C1 N1 C5 C6 171.53(18) . . . . ?
C7 N1 C5 C6 -69.2(2) . . . . ?
C3 N1 C5 C6 49.8(2) . . . . ?
C5 N1 C7 C8 -60.3(2) . . . . ?
C1 N1 C7 C8 58.8(2) . . . . ?
C3 N1 C7 C8 -179.50(17) . . . . ?
N1 C7 C8 C9 95.7(2) . . . . ?
N1 C7 C8 C13 -90.5(2) . . . . ?
C13 C8 C9 F9 -177.09(19) . . . . ?
C7 C8 C9 F9 -3.0(3) . . . . ?
C13 C8 C9 C10 1.7(3) . . . . ?
C7 C8 C9 C10 175.8(2) . . . . ?
F9 C9 C10 F10 -0.1(3) . . . . ?
C8 C9 C10 F10 -178.9(2) . . . . ?
F9 C9 C10 C11 178.5(2) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
F10 C10 C11 F11 -0.4(3) . . . . ?
C9 C10 C11 F11 -179.0(2) . . . . ?
F10 C10 C11 C12 177.8(2) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
F11 C11 C12 F12 0.5(3) . . . . ?
C10 C11 C12 F12 -177.8(2) . . . . ?
F11 C11 C12 C13 178.6(2) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
F12 C12 C13 F13 1.8(3) . . . . ?
C11 C12 C13 F13 -176.38(19) . . . . ?
F12 C12 C13 C8 179.26(19) . . . . ?
C11 C12 C13 C8 1.1(3) . . . . ?
C9 C8 C13 F13 175.33(19) . . . . ?
C7 C8 C13 F13 1.2(3) . . . . ?
C9 C8 C13 C12 -2.1(3) . . . . ?
C7 C8 C13 C12 -176.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.069

_iucr_refine_instructions_details 
;
TITL mm-js-28 in P 21/n
CELL   0.71073   8.0145  13.8741  13.5995  90.000  95.015  90.000
ZERR     4       0.0001   0.0002   0.0002   0.000   0.001   0.000
LATT  1
SYMM 1/2-X,1/2+Y,1/2-Z
SFAC        C       H       N       F       I
UNIT        52      68       4      20       4
L.S.      10
OMIT -3 50.05
OMIT 0 0 8
TEMP  -150
SIZE  0.50 0.25 0.19
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.011700    1.384600
FVAR       0.34391
I1    5    0.289246    0.338101    0.142821    11.00000    0.02840    0.02021 =
         0.01774    0.00252    0.00597    0.00296
F9    4    0.333515    0.192329   -0.169092    11.00000    0.02642    0.02655 =
         0.03886    0.01055   -0.01071   -0.00424
F10   4    0.110269    0.093665   -0.072490    11.00000    0.01872    0.02929 =
         0.08836    0.01389    0.00096   -0.00569
F11   4    0.202030    0.015911    0.107046    11.00000    0.05194    0.02646 =
         0.06084   -0.00062    0.03924   -0.01020
F12   4    0.521685    0.034914    0.188259    11.00000    0.07489    0.02579 =
         0.01792    0.00338    0.01079   -0.00967
F13   4    0.747450    0.129862    0.091690    11.00000    0.03766    0.02486 =
         0.02518    0.00548   -0.00992   -0.00614
N1    3    0.699637    0.326761   -0.074880    11.00000    0.01555    0.01388 =
         0.01546    0.00044    0.00219    0.00018
C1    1    0.751438    0.339066    0.034947    11.00000    0.02142    0.01758 =
         0.01347    0.00012   -0.00009   -0.00076
AFIX  23
H1A   2    0.654382    0.322678    0.072058    11.00000   -1.20000
H1B   2    0.841302    0.292035    0.054208    11.00000   -1.20000
AFIX   0
C2    1    0.812898    0.438702    0.066559    11.00000    0.02696    0.01904 =
         0.02053   -0.00362    0.00116   -0.00165
AFIX  33
H2A   2    0.842602    0.439294    0.138007    11.00000   -1.50000
H2B   2    0.724141    0.486011    0.049808    11.00000   -1.50000
H2C   2    0.911655    0.455165    0.032284    11.00000   -1.50000
AFIX   0
C3    1    0.832499    0.365013   -0.138653    11.00000    0.01718    0.01760 =
         0.01792    0.00181    0.00557   -0.00260
AFIX  23
H3A   2    0.793919    0.353570   -0.208832    11.00000   -1.20000
H3B   2    0.841984    0.435584   -0.128951    11.00000   -1.20000
AFIX   0
C4    1    1.004290    0.320943   -0.117969    11.00000    0.01859    0.02296 =
         0.02523    0.00165    0.00454    0.00084
AFIX  33
H4A   2    1.081145    0.349615   -0.161984    11.00000   -1.50000
H4B   2    0.997546    0.251243   -0.129313    11.00000   -1.50000
H4C   2    1.045653    0.333375   -0.049187    11.00000   -1.50000
AFIX   0
C5    1    0.538228    0.382743   -0.099769    11.00000    0.01513    0.01449 =
         0.02142    0.00064    0.00323    0.00442
AFIX  23
H5A   2    0.447881    0.351559   -0.066031    11.00000   -1.20000
H5B   2    0.553165    0.448674   -0.072575    11.00000   -1.20000
AFIX   0
C6    1    0.481567    0.390504   -0.208933    11.00000    0.02032    0.02370 =
         0.02212    0.00270    0.00011    0.00298
AFIX  33
H6A   2    0.376929    0.427298   -0.217528    11.00000   -1.50000
H6B   2    0.463219    0.325783   -0.236660    11.00000   -1.50000
H6C   2    0.567970    0.423440   -0.243093    11.00000   -1.50000
AFIX   0
C7    1    0.675732    0.219507   -0.096638    11.00000    0.01888    0.01355 =
         0.01659   -0.00137    0.00216    0.00039
AFIX  23
H7A   2    0.643294    0.211552   -0.168101    11.00000   -1.20000
H7B   2    0.784597    0.186581   -0.081737    11.00000   -1.20000
AFIX   0
C8    1    0.546522    0.169885   -0.040035    11.00000    0.02222    0.01228 =
         0.01763   -0.00183    0.00450    0.00043
C9    1    0.383199    0.156614   -0.079331    11.00000    0.02383    0.01344 =
         0.02697    0.00111    0.00218    0.00191
C10   1    0.266637    0.106012   -0.030805    11.00000    0.02066    0.01501 =
         0.05038   -0.00260    0.00811    0.00132
C11   1    0.313082    0.066460    0.059785    11.00000    0.03608    0.01295 =
         0.04083   -0.00328    0.02384   -0.00440
C12   1    0.474303    0.076386    0.100854    11.00000    0.04740    0.01451 =
         0.01898   -0.00315    0.01205   -0.00257
C13   1    0.588647    0.126631    0.050992    11.00000    0.02856    0.01418 =
         0.02016   -0.00244    0.00263    0.00141
HKLF   4
 
REM  mm-js-28 in P 21/n
REM R1 =  0.0189 for   2480 Fo > 4sig(Fo)  and  0.0210 for all   2656 data
REM    181 parameters refined using      0 restraints
 
END
 
WGHT      0.0117      1.3740
REM Highest difference peak  0.476,  deepest hole -0.387,  1-sigma level  0.069
Q1    1   0.5288  0.4566 -0.2343  11.00000  0.05    0.48
Q2    1   0.3630  0.3962 -0.2075  11.00000  0.05    0.31
Q3    1   0.5235  0.3275 -0.2543  11.00000  0.05    0.27
Q4    1   0.9322  0.4399  0.0636  11.00000  0.05    0.27
Q5    1   0.5549  0.1580  0.0123  11.00000  0.05    0.27
Q6    1   0.6754  0.2078 -0.1420  11.00000  0.05    0.25
Q7    1   0.7316  0.3387 -0.0210  11.00000  0.05    0.25
Q8    1   1.0179  0.2665 -0.1593  11.00000  0.05    0.24
Q9    1   0.7617  0.4536  0.1360  11.00000  0.05    0.24
Q10   1   0.4954  0.0664  0.1383  11.00000  0.05    0.24
Q11   1   1.1278  0.3689 -0.1436  11.00000  0.05    0.23
Q12   1   0.6002  0.2017 -0.0671  11.00000  0.05    0.23
Q13   1   0.7649  0.3451 -0.1028  11.00000  0.05    0.22
Q14   1   0.3072  0.0711  0.0036  11.00000  0.05    0.22
Q15   1   0.6951  0.2683 -0.0863  11.00000  0.05    0.22
Q16   1   0.7315  0.5002 -0.0020  11.00000  0.05    0.21
Q17   1   0.5275  0.0884  0.0733  11.00000  0.05    0.21
Q18   1   0.3889  0.0978  0.0927  11.00000  0.05    0.20
Q19   1   0.3973  0.2607  0.0965  11.00000  0.05    0.20
Q20   1   0.7834  0.4837  0.0184  11.00000  0.05    0.20
Q21   1   0.7764  0.3929  0.0452  11.00000  0.05    0.20
Q22   1   1.0381  0.4098  0.1076  11.00000  0.05    0.20
Q23   1   0.7535  0.2154 -0.0785  11.00000  0.05    0.19
Q24   1   0.5538 -0.0396  0.0947  11.00000  0.05    0.19
Q25   1   0.4683  0.1929 -0.0397  11.00000  0.05    0.19
;
_database_code_depnum_ccdc_archive 'CCDC 1005288'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm-357-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H7 F5 N3 O, I'
_chemical_formula_sum            'C12 H7 F5 I N3 O'
_chemical_formula_weight         431.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.7161(3)
_cell_length_b                   11.9730(3)
_cell_length_c                   12.5893(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1464.52(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2087
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.955
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    2.245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5621
_exptl_absorpt_correction_T_max  0.8066
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18585
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         25.24
_reflns_number_total             2647
_reflns_number_gt                2587
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0172P)^2^+1.5964P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.075(19)
_refine_ls_number_reflns         2647
_refine_ls_number_parameters     211
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0204
_refine_ls_R_factor_gt           0.0196
_refine_ls_wR_factor_ref         0.0482
_refine_ls_wR_factor_gt          0.0479
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.94578(2) 1.094927(17) 0.661980(17) 0.02449(7) Uani 1 1 d D . .
F10 F 0.7632(2) 0.27442(17) 0.42851(16) 0.0306(5) Uani 1 1 d . . .
F11 F 0.6578(3) 0.06801(16) 0.41364(17) 0.0362(5) Uani 1 1 d . . .
F12 F 0.5010(2) -0.01568(17) 0.5728(2) 0.0394(6) Uani 1 1 d . . .
F13 F 0.4496(3) 0.10946(19) 0.74829(18) 0.0452(6) Uani 1 1 d . . .
F14 F 0.5483(3) 0.31823(18) 0.76276(17) 0.0383(5) Uani 1 1 d . . .
O8 O 0.7843(3) 0.4440(2) 0.6868(2) 0.0342(6) Uani 1 1 d . . .
N1 N 0.7912(3) 0.6490(2) 0.6043(2) 0.0216(6) Uani 1 1 d D . .
H1 H 0.814(4) 0.608(3) 0.657(2) 0.026 Uiso 1 1 d D . .
N6 N 0.8742(4) 0.8011(2) 0.6963(2) 0.0305(7) Uani 1 1 d D . .
H6A H 0.904(4) 0.757(3) 0.746(3) 0.037 Uiso 1 1 d D . .
H6B H 0.890(4) 0.8754(13) 0.700(3) 0.037 Uiso 1 1 d D . .
N7 N 0.6930(3) 0.4879(2) 0.5260(2) 0.0239(6) Uani 1 1 d D . .
H7 H 0.644(4) 0.462(3) 0.473(2) 0.029 Uiso 1 1 d D . .
C2 C 0.7264(3) 0.6007(3) 0.5196(3) 0.0221(7) Uani 1 1 d . . .
C3 C 0.6931(4) 0.6632(3) 0.4324(3) 0.0267(8) Uani 1 1 d . . .
H3 H 0.6511 0.6299 0.3720 0.032 Uiso 1 1 calc R . .
C4 C 0.7225(4) 0.7772(3) 0.4345(3) 0.0288(8) Uani 1 1 d . . .
H4 H 0.6996 0.8218 0.3746 0.035 Uiso 1 1 calc R . .
C5 C 0.7832(4) 0.8265(3) 0.5203(3) 0.0268(8) Uani 1 1 d . . .
H5 H 0.8020 0.9044 0.5204 0.032 Uiso 1 1 calc R . .
C6 C 0.8176(4) 0.7602(3) 0.6088(3) 0.0244(7) Uani 1 1 d . . .
C8 C 0.7190(4) 0.4178(3) 0.6088(3) 0.0256(8) Uani 1 1 d . . .
C9 C 0.6588(4) 0.3032(3) 0.5956(3) 0.0231(7) Uani 1 1 d . . .
C10 C 0.6825(4) 0.2370(3) 0.5075(3) 0.0220(7) Uani 1 1 d . . .
C11 C 0.6298(4) 0.1301(3) 0.4990(3) 0.0260(8) Uani 1 1 d . . .
C12 C 0.5514(4) 0.0877(3) 0.5804(3) 0.0274(7) Uani 1 1 d . . .
C13 C 0.5271(3) 0.1507(3) 0.6693(3) 0.0291(8) Uani 1 1 d . . .
C14 C 0.5799(3) 0.2571(3) 0.6766(3) 0.0260(8) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.02701(11) 0.02009(10) 0.02638(11) -0.00279(9) -0.00166(10) 0.00113(10)
F10 0.0401(13) 0.0244(11) 0.0273(10) 0.0001(9) 0.0077(10) -0.0027(10)
F11 0.0571(15) 0.0207(11) 0.0308(11) -0.0051(8) -0.0013(11) -0.0011(10)
F12 0.0415(13) 0.0208(10) 0.0561(14) 0.0019(10) -0.0039(11) -0.0135(9)
F13 0.0461(13) 0.0392(13) 0.0504(13) 0.0066(10) 0.0192(12) -0.0137(14)
F14 0.0463(13) 0.0353(11) 0.0334(11) -0.0076(9) 0.0100(12) -0.0020(12)
O8 0.0476(16) 0.0247(12) 0.0302(15) 0.0029(10) -0.0168(13) -0.0106(12)
N1 0.0284(16) 0.0168(14) 0.0196(14) 0.0043(11) 0.0000(13) 0.0009(12)
N6 0.050(2) 0.0166(15) 0.0251(15) -0.0002(12) -0.0080(14) -0.0046(14)
N7 0.0286(17) 0.0170(14) 0.0261(15) -0.0024(12) -0.0061(13) -0.0050(12)
C2 0.0227(16) 0.0206(16) 0.0230(16) -0.0064(15) 0.0044(13) -0.0038(16)
C3 0.034(2) 0.0227(19) 0.0234(17) -0.0008(14) -0.0053(16) -0.0045(16)
C4 0.036(2) 0.0243(19) 0.0264(18) 0.0071(15) -0.0057(17) 0.0020(16)
C5 0.036(2) 0.0149(15) 0.0294(18) 0.0032(14) -0.0029(17) 0.0003(15)
C6 0.0284(19) 0.0197(17) 0.0250(17) -0.0017(14) 0.0027(16) -0.0048(15)
C8 0.0245(17) 0.0214(18) 0.0307(18) -0.0005(16) 0.0003(15) -0.0020(16)
C9 0.0240(18) 0.0210(18) 0.0242(17) 0.0031(14) -0.0036(15) 0.0010(15)
C10 0.0253(18) 0.0162(16) 0.0245(16) 0.0040(13) -0.0021(16) -0.0025(13)
C11 0.0328(19) 0.0186(16) 0.0266(18) -0.0020(14) -0.0087(17) 0.0032(14)
C12 0.0239(16) 0.0195(16) 0.0386(18) -0.0002(15) -0.0095(17) -0.0067(19)
C13 0.0221(18) 0.0283(17) 0.0370(19) 0.0066(17) 0.0024(17) -0.0015(14)
C14 0.0250(19) 0.0245(17) 0.0285(18) -0.0003(14) 0.0016(15) 0.0003(14)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F10 C10 1.343(4) . ?
F11 C11 1.334(4) . ?
F12 C12 1.334(4) . ?
F13 C13 1.342(4) . ?
F14 C14 1.344(4) . ?
O8 C8 1.210(4) . ?
N1 C6 1.357(4) . ?
N1 C2 1.366(4) . ?
N1 H1 0.85(2) . ?
N6 C6 1.326(5) . ?
N6 H6A 0.87(2) . ?
N6 H6B 0.905(15) . ?
N7 C8 1.362(5) . ?
N7 C2 1.391(5) . ?
N7 H7 0.88(2) . ?
C2 C3 1.368(5) . ?
C3 C4 1.395(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.365(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.407(5) . ?
C5 H5 0.9500 . ?
C8 C9 1.501(5) . ?
C9 C10 1.383(5) . ?
C9 C14 1.389(5) . ?
C10 C11 1.383(5) . ?
C11 C12 1.374(5) . ?
C12 C13 1.370(5) . ?
C13 C14 1.376(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C2 122.3(3) . . ?
C6 N1 H1 119(3) . . ?
C2 N1 H1 119(3) . . ?
C6 N6 H6A 121(3) . . ?
C6 N6 H6B 119(3) . . ?
H6A N6 H6B 120(4) . . ?
C8 N7 C2 126.8(3) . . ?
C8 N7 H7 118(3) . . ?
C2 N7 H7 115(3) . . ?
N1 C2 C3 120.3(3) . . ?
N1 C2 N7 118.2(3) . . ?
C3 C2 N7 121.5(3) . . ?
C2 C3 C4 118.1(3) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 121.8(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 119.0(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
N6 C6 N1 118.4(3) . . ?
N6 C6 C5 123.2(3) . . ?
N1 C6 C5 118.4(3) . . ?
O8 C8 N7 123.9(3) . . ?
O8 C8 C9 122.1(3) . . ?
N7 C8 C9 114.0(3) . . ?
C10 C9 C14 116.9(3) . . ?
C10 C9 C8 123.2(3) . . ?
C14 C9 C8 119.8(3) . . ?
F10 C10 C11 117.9(3) . . ?
F10 C10 C9 120.0(3) . . ?
C11 C10 C9 122.1(3) . . ?
F11 C11 C12 120.5(3) . . ?
F11 C11 C10 120.2(3) . . ?
C12 C11 C10 119.3(3) . . ?
F12 C12 C13 120.4(3) . . ?
F12 C12 C11 119.5(3) . . ?
C13 C12 C11 120.1(3) . . ?
F13 C13 C12 119.9(3) . . ?
F13 C13 C14 120.1(3) . . ?
C12 C13 C14 120.0(3) . . ?
F14 C14 C13 118.2(3) . . ?
F14 C14 C9 120.1(3) . . ?
C13 C14 C9 121.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 4.0(5) . . . . ?
C6 N1 C2 N7 -174.5(3) . . . . ?
C8 N7 C2 N1 -0.6(5) . . . . ?
C8 N7 C2 C3 -179.1(4) . . . . ?
N1 C2 C3 C4 -2.3(6) . . . . ?
N7 C2 C3 C4 176.2(3) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C2 N1 C6 N6 176.4(3) . . . . ?
C2 N1 C6 C5 -3.4(5) . . . . ?
C4 C5 C6 N6 -178.6(4) . . . . ?
C4 C5 C6 N1 1.2(5) . . . . ?
C2 N7 C8 O8 -5.1(6) . . . . ?
C2 N7 C8 C9 174.7(3) . . . . ?
O8 C8 C9 C10 -126.4(4) . . . . ?
N7 C8 C9 C10 53.7(5) . . . . ?
O8 C8 C9 C14 50.5(5) . . . . ?
N7 C8 C9 C14 -129.3(4) . . . . ?
C14 C9 C10 F10 -176.9(3) . . . . ?
C8 C9 C10 F10 0.2(5) . . . . ?
C14 C9 C10 C11 0.5(5) . . . . ?
C8 C9 C10 C11 177.6(3) . . . . ?
F10 C10 C11 F11 -1.0(5) . . . . ?
C9 C10 C11 F11 -178.4(3) . . . . ?
F10 C10 C11 C12 177.4(3) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
F11 C11 C12 F12 -1.2(5) . . . . ?
C10 C11 C12 F12 -179.6(3) . . . . ?
F11 C11 C12 C13 177.8(3) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
F12 C12 C13 F13 -1.6(5) . . . . ?
C11 C12 C13 F13 179.5(3) . . . . ?
F12 C12 C13 C14 179.7(3) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
F13 C13 C14 F14 -1.8(5) . . . . ?
C12 C13 C14 F14 176.8(3) . . . . ?
F13 C13 C14 C9 -179.0(3) . . . . ?
C12 C13 C14 C9 -0.3(5) . . . . ?
C10 C9 C14 F14 -177.4(3) . . . . ?
C8 C9 C14 F14 5.4(5) . . . . ?
C10 C9 C14 C13 -0.4(5) . . . . ?
C8 C9 C14 C13 -177.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O8 0.85(2) 2.02(3) 2.666(4) 131(3) .
N6 H6A I1 0.87(2) 2.69(2) 3.512(3) 158(4) 4_746
N6 H6B I1 0.905(15) 2.725(15) 3.611(3) 167(3) .
N7 H7 I1 0.88(2) 2.65(2) 3.515(3) 166(3) 3_466

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.067

_iucr_refine_instructions_details 
;
TITL mm-357-1 in P 21 21 21
CELL   0.71073   9.7161  11.9730  12.5893  90.000  90.000  90.000
ZERR     4       0.0003   0.0003   0.0003   0.000   0.000   0.000
LATT -1
SYMM 1/2-X,-Y,1/2+Z
SYMM 1/2+X,1/2-Y,-Z
SYMM -X,1/2+Y,1/2-Z
SFAC        C       H       N       O       F       I
UNIT        48      28      12      4       20      4
OMIT -3 50.5
OMIT 0 0 2
L.S.      10
TEMP  -150
SIZE  0.29 0.11 0.10
EQIV $1 -x+2, y-1/2, -z+3/2
EQIV $2 x-1/2, -y+3/2, -z+1
HTAB N1 O8
HTAB N6 I1_$1
HTAB N6 I1
HTAB N7 I1_$2
ACTA
CONF
HTAB
BOND $H
FMAP      2
PLAN     25
WGHT    0.017200    1.596400
FVAR       0.46868
I1    6    0.945784    1.094927    0.661980    11.00000    0.02701    0.02009 =
         0.02638   -0.00279   -0.00166    0.00113
F10   5    0.763196    0.274423    0.428510    11.00000    0.04010    0.02442 =
         0.02734    0.00015    0.00768   -0.00274
F11   5    0.657765    0.068013    0.413641    11.00000    0.05711    0.02070 =
         0.03084   -0.00508   -0.00128   -0.00105
F12   5    0.501042   -0.015682    0.572810    11.00000    0.04148    0.02076 =
         0.05606    0.00190   -0.00387   -0.01351
F13   5    0.449637    0.109462    0.748292    11.00000    0.04609    0.03920 =
         0.05041    0.00665    0.01917   -0.01367
F14   5    0.548346    0.318231    0.762760    11.00000    0.04630    0.03528 =
         0.03339   -0.00755    0.00997   -0.00203
O8    4    0.784333    0.444000    0.686768    11.00000    0.04761    0.02470 =
         0.03018    0.00292   -0.01682   -0.01055
N1    3    0.791153    0.648983    0.604269    11.00000    0.02842    0.01677 =
         0.01959    0.00425    0.00000    0.00089
H1    2    0.814040    0.608333    0.657077    11.00000   -1.20000
DFIX 0.88 N1 H1
N6    3    0.874246    0.801141    0.696304    11.00000    0.04984    0.01663 =
         0.02514   -0.00023   -0.00799   -0.00465
H6A   2    0.904283    0.757095    0.746204    11.00000   -1.20000
H6B   2    0.890421    0.875445    0.700197    11.00000   -1.20000
DFIX 0.91 N6 H6A N6 H6B
DFIX 2.7 H6B I1
N7    3    0.693029    0.487921    0.526037    11.00000    0.02856    0.01698 =
         0.02612   -0.00244   -0.00615   -0.00502
H7    2    0.643775    0.462473    0.472570    11.00000   -1.20000
DFIX 0.91 N7 H7
C2    1    0.726383    0.600699    0.519629    11.00000    0.02271    0.02064 =
         0.02303   -0.00638    0.00441   -0.00385
C3    1    0.693054    0.663227    0.432356    11.00000    0.03418    0.02269 =
         0.02336   -0.00082   -0.00530   -0.00451
AFIX  43
H3    2    0.651074    0.629925    0.372010    11.00000   -1.20000
AFIX   0
C4    1    0.722454    0.777249    0.434493    11.00000    0.03581    0.02433 =
         0.02635    0.00713   -0.00568    0.00203
AFIX  43
H4    2    0.699604    0.821825    0.374608    11.00000   -1.20000
AFIX   0
C5    1    0.783193    0.826497    0.520350    11.00000    0.03612    0.01486 =
         0.02942    0.00320   -0.00290    0.00030
AFIX  43
H5    2    0.801955    0.904368    0.520414    11.00000   -1.20000
AFIX   0
C6    1    0.817594    0.760181    0.608753    11.00000    0.02840    0.01971 =
         0.02503   -0.00171    0.00273   -0.00481
C8    1    0.719041    0.417796    0.608816    11.00000    0.02453    0.02143 =
         0.03069   -0.00053    0.00034   -0.00198
C9    1    0.658768    0.303237    0.595617    11.00000    0.02404    0.02096 =
         0.02420    0.00315   -0.00361    0.00102
C10   1    0.682460    0.237027    0.507465    11.00000    0.02526    0.01623 =
         0.02449    0.00404   -0.00214   -0.00246
C11   1    0.629802    0.130085    0.498978    11.00000    0.03284    0.01857 =
         0.02661   -0.00200   -0.00869    0.00320
C12   1    0.551384    0.087686    0.580392    11.00000    0.02391    0.01951 =
         0.03864   -0.00016   -0.00946   -0.00667
C13   1    0.527129    0.150732    0.669297    11.00000    0.02208    0.02829 =
         0.03698    0.00663    0.00236   -0.00147
C14   1    0.579938    0.257117    0.676566    11.00000    0.02500    0.02452 =
         0.02852   -0.00029    0.00164    0.00031
HKLF   4
 
REM  mm-357-1 in P 21 21 21
REM R1 =  0.0196 for   2587 Fo > 4sig(Fo)  and  0.0204 for all   2647 data
REM    211 parameters refined using      5 restraints
 
END
 
WGHT      0.0172      1.6091
REM Highest difference peak  0.298,  deepest hole -0.365,  1-sigma level  0.067
Q1    1   1.0175  1.0491  0.6336  11.00000  0.05    0.30
Q2    1   0.7546  0.7843  0.4810  11.00000  0.05    0.28
Q3    1   0.5551  0.2084  0.6640  11.00000  0.05    0.28
Q4    1   0.6849  0.3569  0.6007  11.00000  0.05    0.26
Q5    1   0.5556  0.1056  0.6355  11.00000  0.05    0.25
Q6    1   0.8465  0.7010  0.6001  11.00000  0.05    0.24
Q7    1   0.8493  0.4327  0.6477  11.00000  0.05    0.24
Q8    1   0.5724  0.2916  0.6369  11.00000  0.05    0.24
Q9    1   0.8210  0.7863  0.5586  11.00000  0.05    0.24
Q10   1   0.6999  0.2635  0.5568  11.00000  0.05    0.24
Q11   1   0.5433  0.0482  0.5768  11.00000  0.05    0.24
Q12   1   0.6024  0.0940  0.5560  11.00000  0.05    0.23
Q13   1   0.9243  0.7735  0.7193  11.00000  0.05    0.23
Q14   1   0.7144  0.5443  0.5179  11.00000  0.05    0.22
Q15   1   0.7189  0.0957  0.4315  11.00000  0.05    0.22
Q16   1   0.5014  0.1384  0.6978  11.00000  0.05    0.22
Q17   1   0.6314  0.1963  0.4981  11.00000  0.05    0.22
Q18   1   0.5692  0.1427  0.6960  11.00000  0.05    0.21
Q19   1   0.5213  0.0983  0.7781  11.00000  0.05    0.21
Q20   1   0.7487  0.6233  0.5628  11.00000  0.05    0.21
Q21   1   0.6834  0.0209  0.4247  11.00000  0.05    0.21
Q22   1   0.6561  0.0997  0.4614  11.00000  0.05    0.20
Q23   1   0.7309  0.4005  0.7096  11.00000  0.05    0.20
Q24   1   0.5320  0.2637  0.8022  11.00000  0.05    0.20
Q25   1   0.7728  1.0942  0.6569  11.00000  0.05    0.20
;
_database_code_depnum_ccdc_archive 'CCDC 1005289'
   0.19
Q18   1   1.0403  0.0314  0.2999  11.00000  0.05    0.19
Q19   1   0.8209  0.2212  0.3399  11.00000  0.05    0.19
Q20   1   0.8959  0.2848  0.4753  11.00000  0.05    0.19
Q21   1   0.8883  0.1174  0.3205  11.00000  0.05    0.18
Q22   1   0.3583  0.5937  0.4769  11.00000  0.05    0.18
Q23   1   0.7008  0.4088  0.3593  11.00000  0.05    0.18
Q24   1   0.5269  0.6982  0.4744  11.00000  0.05    0.17
Q25   1   0.6782  0.3086  0.3100  11.00000  0.05    0.17
;
_database_code_depnum_ccdc_archive 'CCDC 1005277'
