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

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#
#                 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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#
#  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.
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data_al261

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 F5 N4 O4 S'
_chemical_formula_weight         440.35

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   9.4590(3)
_cell_length_b                   22.4257(8)
_cell_length_c                   9.0101(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.656(2)
_cell_angle_gamma                90.00
_cell_volume                     1722.83(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4723
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      30.27

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9945
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating anode X-ray tube'
_diffrn_source_type              'Bruker-Nonius FR 591'
_diffrn_source_power             50
_diffrn_source_current           70
_diffrn_source_size              '0.3 mm x 0.3 mm fine focus'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            12909
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         30.35
_reflns_number_total             4853
_reflns_number_gt                3846
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    'SHELXS-2012 (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2sigma(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)+(0.0625P)²+1.5116P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4853
_refine_ls_number_parameters     318
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1441
_refine_ls_wR_factor_gt          0.1338
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.105
_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
S1 S 0.69409(7) 0.13115(2) 0.13056(7) 0.02618(14) Uani 1 1 d . . .
N1 N 0.7143(2) 0.09773(8) 0.3010(2) 0.0257(4) Uani 1 1 d . . .
H1 H 0.6344 0.0992 0.3265 0.031 Uiso 1 1 calc R . .
N2 N 0.8361(2) 0.04289(8) 0.5423(2) 0.0232(4) Uani 1 1 d . . .
H2A H 0.9171 0.0210 0.6054 0.028 Uiso 1 1 calc R . .
N3 N 0.5912(2) 0.07881(8) 0.5083(2) 0.0228(3) Uani 1 1 d . . .
N4 N 0.7495(2) 0.01613(8) 0.7334(2) 0.0226(3) Uani 1 1 d . . .
O1 O 0.7805(2) 0.09935(7) 0.0599(2) 0.0316(4) Uani 1 1 d . . .
O2 O 0.5293(2) 0.13876(8) 0.0390(2) 0.0363(4) Uani 1 1 d . . .
O3 O 0.96398(18) 0.06153(7) 0.3864(2) 0.0279(3) Uani 1 1 d . . .
O4 O 0.65251(19) -0.01514(7) 0.9149(2) 0.0285(3) Uani 1 1 d . . .
C1 C 0.7815(3) 0.20144(9) 0.1920(3) 0.0248(4) Uani 1 1 d . . .
C2 C 0.9215(3) 0.20990(10) 0.1810(3) 0.0289(5) Uani 1 1 d . . .
H2 H 0.9697 0.1780 0.1508 0.035 Uiso 1 1 calc R . .
C3 C 0.9902(3) 0.26591(12) 0.2151(3) 0.0334(5) Uani 1 1 d . A .
C4 C 0.9188(3) 0.31194(10) 0.2595(3) 0.0336(5) Uani 1 1 d . . .
H4 H 0.9654 0.3504 0.2811 0.040 Uiso 1 1 calc R . .
C5 C 0.7818(3) 0.30253(10) 0.2725(3) 0.0341(5) Uani 1 1 d . . .
H5 H 0.7354 0.3348 0.3037 0.041 Uiso 1 1 calc R . .
C6 C 0.7084(3) 0.24731(10) 0.2416(3) 0.0289(5) Uani 1 1 d . . .
C7 C 0.5619(3) 0.23884(13) 0.2642(4) 0.0387(6) Uani 1 1 d . . .
H7A H 0.5361 0.2761 0.3040 0.058 Uiso 1 1 calc R . .
H7B H 0.5784 0.2071 0.3448 0.058 Uiso 1 1 calc R . .
H7C H 0.4753 0.2278 0.1588 0.058 Uiso 1 1 calc R . .
C8 C 1.1411(3) 0.27614(13) 0.2048(3) 0.0463(7) Uani 1 1 d D . .
C9 C 0.8467(3) 0.06754(9) 0.4074(3) 0.0229(4) Uani 1 1 d . . .
C10 C 0.7186(2) 0.04687(8) 0.5954(3) 0.0212(4) Uani 1 1 d . . .
C11 C 0.4789(2) 0.08082(9) 0.5642(3) 0.0249(4) Uani 1 1 d . . .
C12 C 0.4974(3) 0.05001(10) 0.7033(3) 0.0267(4) Uani 1 1 d . . .
H12 H 0.4199 0.0507 0.7438 0.032 Uiso 1 1 calc R . .
C13 C 0.6354(3) 0.01784(9) 0.7814(3) 0.0240(4) Uani 1 1 d . . .
C14 C 0.3390(3) 0.11852(11) 0.4677(3) 0.0321(5) Uani 1 1 d . . .
H14A H 0.3653 0.1606 0.4956 0.048 Uiso 1 1 calc R . .
H14B H 0.2526 0.1071 0.4943 0.048 Uiso 1 1 calc R . .
H14C H 0.3072 0.1126 0.3497 0.048 Uiso 1 1 calc R . .
C15 C 0.8018(3) -0.03323(10) 1.0195(3) 0.0302(5) Uani 1 1 d . . .
H15 H 0.8806 -0.0014 1.0335 0.036 Uiso 1 1 calc R . .
F1 F 1.2578(9) 0.2860(4) 0.3430(8) 0.0477(19) Uani 0.40 1 d PDU A 1
F2 F 1.1202(13) 0.3184(4) 0.0930(11) 0.072(3) Uani 0.40 1 d PDU A 1
F3 F 1.1841(6) 0.2252(2) 0.1422(8) 0.0360(11) Uani 0.40 1 d PDU A 1
F1' F 1.2685(8) 0.2602(3) 0.3526(8) 0.0528(17) Uani 0.40 1 d PD A 2
F2' F 1.1773(8) 0.3368(2) 0.2024(13) 0.081(2) Uani 0.40 1 d PD A 2
F3' F 1.1628(8) 0.2506(4) 0.0931(8) 0.0646(18) Uani 0.40 1 d PDU A 2
F1" F 1.2370(16) 0.3099(5) 0.3226(14) 0.054(4) Uani 0.20 1 d PDU A 3
F2" F 1.110(2) 0.3026(7) 0.0589(13) 0.059(4) Uani 0.20 1 d PDU A 3
F3" F 1.207(2) 0.2234(5) 0.199(2) 0.088(7) Uani 0.20 1 d PDU A 3
F4 F 0.79779(19) -0.04619(7) 1.16313(18) 0.0379(4) Uani 1 1 d . . .
F5 F 0.8378(2) -0.08431(7) 0.9655(2) 0.0456(4) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds 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 O2 1.4233(18) . ?
S1 O1 1.4262(17) . ?
S1 N1 1.6444(19) . ?
S1 C1 1.754(2) . ?
N1 C9 1.381(3) . ?
N2 C9 1.378(3) . ?
N2 C10 1.390(3) . ?
N3 C10 1.327(3) . ?
N3 C11 1.359(3) . ?
N4 C13 1.326(3) . ?
N4 C10 1.338(3) . ?
O3 C9 1.211(3) . ?
O4 C13 1.360(3) . ?
O4 C15 1.377(3) . ?
C1 C2 1.384(3) . ?
C1 C6 1.415(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.384(4) . ?
C3 C8 1.488(4) . ?
C4 C5 1.367(4) . ?
C5 C6 1.388(3) . ?
C6 C7 1.498(3) . ?
C8 F3' 1.250(6) . ?
C8 F1 1.276(6) . ?
C8 F1" 1.299(8) . ?
C8 F2 1.334(6) . ?
C8 F3" 1.348(9) . ?
C8 F2" 1.354(9) . ?
C8 F1' 1.400(6) . ?
C8 F2' 1.405(5) . ?
C8 F3 1.410(6) . ?
C11 C12 1.375(3) . ?
C11 C14 1.492(3) . ?
C12 C13 1.387(3) . ?
C15 F4 1.343(3) . ?
C15 F5 1.345(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
O2 S1 O1 119.78(11) . . ?
O2 S1 N1 104.56(10) . . ?
O1 S1 N1 109.39(10) . . ?
O2 S1 C1 108.86(11) . . ?
O1 S1 C1 107.91(11) . . ?
N1 S1 C1 105.45(10) . . ?
C9 N1 S1 125.13(15) . . ?
C9 N2 C10 130.71(18) . . ?
C10 N3 C11 117.01(19) . . ?
C13 N4 C10 114.04(18) . . ?
C13 O4 C15 117.35(17) . . ?
C2 C1 C6 122.4(2) . . ?
C2 C1 S1 115.81(17) . . ?
C6 C1 S1 121.67(18) . . ?
C1 C2 C3 118.7(2) . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 C8 120.3(2) . . ?
C2 C3 C8 119.8(2) . . ?
C5 C4 C3 120.6(2) . . ?
C4 C5 C6 122.1(2) . . ?
C5 C6 C1 116.2(2) . . ?
C5 C6 C7 119.9(2) . . ?
C1 C6 C7 123.9(2) . . ?
F3' C8 F1 119.4(6) . . ?
F3' C8 F1" 128.7(8) . . ?
F1 C8 F1" 25.8(5) . . ?
F3' C8 F2 74.9(6) . . ?
F1 C8 F2 113.4(6) . . ?
F1" C8 F2 91.4(8) . . ?
F3' C8 F3" 47.6(7) . . ?
F1 C8 F3" 88.4(9) . . ?
F1" C8 F3" 111.9(10) . . ?
F2 C8 F3" 120.8(10) . . ?
F3' C8 F2" 57.4(8) . . ?
F1 C8 F2" 127.2(9) . . ?
F1" C8 F2" 108.6(9) . . ?
F2 C8 F2" 19.4(8) . . ?
F3" C8 F2" 104.7(9) . . ?
F3' C8 F1' 106.0(6) . . ?
F1 C8 F1' 24.7(3) . . ?
F1" C8 F1' 50.5(6) . . ?
F2 C8 F1' 133.2(6) . . ?
F3" C8 F1' 66.0(8) . . ?
F2" C8 F1' 140.4(9) . . ?
F3' C8 F2' 107.8(5) . . ?
F1 C8 F2' 74.6(5) . . ?
F1" C8 F2' 50.2(6) . . ?
F2 C8 F2' 42.1(5) . . ?
F3" C8 F2' 136.7(9) . . ?
F2" C8 F2' 60.9(7) . . ?
F1' C8 F2' 98.4(5) . . ?
F3' C8 F3 29.6(4) . . ?
F1 C8 F3 104.7(5) . . ?
F1" C8 F3 125.4(8) . . ?
F2 C8 F3 104.4(6) . . ?
F3" C8 F3 19.0(7) . . ?
F2" C8 F3 86.9(8) . . ?
F1' C8 F3 84.0(5) . . ?
F2' C8 F3 131.6(4) . . ?
F3' C8 C3 118.4(4) . . ?
F1 C8 C3 114.5(5) . . ?
F1" C8 C3 112.9(8) . . ?
F2 C8 C3 108.9(5) . . ?
F3" C8 C3 109.9(8) . . ?
F2" C8 C3 108.5(9) . . ?
F1' C8 C3 110.8(4) . . ?
F2' C8 C3 113.4(3) . . ?
F3 C8 C3 110.5(3) . . ?
O3 C9 N2 121.0(2) . . ?
O3 C9 N1 124.3(2) . . ?
N2 C9 N1 114.72(18) . . ?
N3 C10 N4 127.16(19) . . ?
N3 C10 N2 119.18(19) . . ?
N4 C10 N2 113.65(18) . . ?
N3 C11 C12 120.6(2) . . ?
N3 C11 C14 116.2(2) . . ?
C12 C11 C14 123.2(2) . . ?
C11 C12 C13 116.40(19) . . ?
N4 C13 O4 118.1(2) . . ?
N4 C13 C12 124.7(2) . . ?
O4 C13 C12 117.20(19) . . ?
F4 C15 F5 106.35(18) . . ?
F4 C15 O4 105.94(19) . . ?
F5 C15 O4 110.4(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
O2 S1 N1 C9 162.08(19) . . . . ?
O1 S1 N1 C9 32.6(2) . . . . ?
C1 S1 N1 C9 -83.2(2) . . . . ?
O2 S1 C1 C2 -139.05(18) . . . . ?
O1 S1 C1 C2 -7.6(2) . . . . ?
N1 S1 C1 C2 109.23(18) . . . . ?
O2 S1 C1 C6 37.9(2) . . . . ?
O1 S1 C1 C6 169.32(18) . . . . ?
N1 S1 C1 C6 -73.9(2) . . . . ?
C6 C1 C2 C3 -2.0(3) . . . . ?
S1 C1 C2 C3 174.88(18) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C1 C2 C3 C8 179.8(2) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C8 C3 C4 C5 -178.6(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C1 -1.4(4) . . . . ?
C4 C5 C6 C7 177.5(2) . . . . ?
C2 C1 C6 C5 2.6(3) . . . . ?
S1 C1 C6 C5 -174.15(18) . . . . ?
C2 C1 C6 C7 -176.3(2) . . . . ?
S1 C1 C6 C7 7.0(3) . . . . ?
C4 C3 C8 F3' -142.8(6) . . . . ?
C2 C3 C8 F3' 37.6(6) . . . . ?
C4 C3 C8 F1 67.9(5) . . . . ?
C2 C3 C8 F1 -111.6(5) . . . . ?
C4 C3 C8 F1" 39.8(7) . . . . ?
C2 C3 C8 F1" -139.8(7) . . . . ?
C4 C3 C8 F2 -60.2(6) . . . . ?
C2 C3 C8 F2 120.3(6) . . . . ?
C4 C3 C8 F3" 165.5(9) . . . . ?
C2 C3 C8 F3" -14.1(9) . . . . ?
C4 C3 C8 F2" -80.6(8) . . . . ?
C2 C3 C8 F2" 99.9(8) . . . . ?
C4 C3 C8 F1' 94.4(4) . . . . ?
C2 C3 C8 F1' -85.1(4) . . . . ?
C4 C3 C8 F2' -15.1(6) . . . . ?
C2 C3 C8 F2' 165.3(5) . . . . ?
C4 C3 C8 F3 -174.2(4) . . . . ?
C2 C3 C8 F3 6.2(5) . . . . ?
C10 N2 C9 O3 175.9(2) . . . . ?
C10 N2 C9 N1 -5.2(3) . . . . ?
S1 N1 C9 O3 -0.9(3) . . . . ?
S1 N1 C9 N2 -179.77(15) . . . . ?
C11 N3 C10 N4 -0.1(3) . . . . ?
C11 N3 C10 N2 179.29(18) . . . . ?
C13 N4 C10 N3 1.8(3) . . . . ?
C13 N4 C10 N2 -177.59(17) . . . . ?
C9 N2 C10 N3 0.1(3) . . . . ?
C9 N2 C10 N4 179.6(2) . . . . ?
C10 N3 C11 C12 -1.1(3) . . . . ?
C10 N3 C11 C14 178.12(18) . . . . ?
N3 C11 C12 C13 0.4(3) . . . . ?
C14 C11 C12 C13 -178.8(2) . . . . ?
C10 N4 C13 O4 176.05(17) . . . . ?
C10 N4 C13 C12 -2.5(3) . . . . ?
C15 O4 C13 N4 19.2(3) . . . . ?
C15 O4 C13 C12 -162.10(19) . . . . ?
C11 C12 C13 N4 1.6(3) . . . . ?
C11 C12 C13 O4 -177.02(18) . . . . ?
C13 O4 C15 F4 159.72(17) . . . . ?
C13 O4 C15 F5 -85.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.936
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.073
_database_code_depnum_ccdc_archive 'CCDC 993889'
#######################################################################
#
#                 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_al262

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 Cl F6 N5 O2'
_chemical_formula_weight         533.86

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   21.4875(9)
_cell_length_b                   20.5465(9)
_cell_length_c                   21.5438(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     9511.4(7)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9628
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      29.16

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4352
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9953
_exptl_absorpt_correction_T_max  0.9976
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating anode X-ray tube'
_diffrn_source_type              'Bruker-Nonius FR 591'
_diffrn_source_power             50
_diffrn_source_current           70
_diffrn_source_size              '0.3 mm x 0.3 mm fine focus'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            87013
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         29.62
_reflns_number_total             13342
_reflns_number_gt                9493
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    'SHELXS-2012 (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2sigma(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)+(0.0629P)²+6.8264P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         13342
_refine_ls_number_parameters     867
_refine_ls_number_restraints     463
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1403
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.048
_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
C1A C 0.43956(10) 0.03492(10) 0.30688(10) 0.0286(4) Uani 1 1 d . . .
C2A C 0.47492(11) -0.01253(11) 0.33645(11) 0.0358(5) Uani 1 1 d . . .
H2A H 0.5183 -0.0163 0.3288 0.043 Uiso 1 1 calc R . .
C3A C 0.44514(12) -0.05399(10) 0.37717(11) 0.0392(6) Uani 1 1 d . . .
H3A H 0.4678 -0.0870 0.3983 0.047 Uiso 1 1 calc R . .
C4A C 0.38199(12) -0.04696(10) 0.38688(11) 0.0360(5) Uani 1 1 d . . .
H4A H 0.3618 -0.0763 0.4144 0.043 Uiso 1 1 calc R . .
C5A C 0.37682(9) 0.03894(8) 0.32103(8) 0.0214(4) Uani 1 1 d . B .
C6A C 0.26363(10) 0.11696(9) 0.23430(9) 0.0262(4) Uani 1 1 d . B .
C7A C 0.21220(11) 0.11073(10) 0.18817(11) 0.0358(5) Uani 1 1 d . . .
C8A C 0.28415(9) 0.17305(9) 0.26468(9) 0.0254(4) Uani 1 1 d . . .
H8A H 0.2686 0.2161 0.2607 0.031 Uiso 1 1 calc R B .
C9A C 0.33218(9) 0.15154(8) 0.30177(8) 0.0204(3) Uani 1 1 d . B .
C10A C 0.36846(9) 0.18380(8) 0.35190(8) 0.0204(3) Uani 1 1 d . . .
C11A C 0.36877(8) 0.28362(8) 0.41478(8) 0.0174(3) Uani 1 1 d . . .
C12A C 0.31997(8) 0.31628(9) 0.44541(8) 0.0200(3) Uani 1 1 d . B .
C13A C 0.33384(9) 0.35514(9) 0.49605(8) 0.0219(4) Uani 1 1 d . . .
H13A H 0.3014 0.3783 0.5164 0.026 Uiso 1 1 calc R B .
C14A C 0.39455(9) 0.36074(9) 0.51752(8) 0.0217(4) Uani 1 1 d . B .
C15A C 0.44217(8) 0.32666(8) 0.48886(8) 0.0192(3) Uani 1 1 d . . .
H15A H 0.4834 0.3295 0.5046 0.023 Uiso 1 1 calc R B .
C16A C 0.42983(8) 0.28813(8) 0.43698(8) 0.0173(3) Uani 1 1 d . A .
C17A C 0.25326(9) 0.30765(10) 0.42498(9) 0.0275(4) Uani 1 1 d . . .
H17A H 0.2256 0.3299 0.4543 0.041 Uiso 1 1 calc R B .
H17B H 0.2431 0.2612 0.4239 0.041 Uiso 1 1 calc R . .
H17C H 0.2478 0.3263 0.3835 0.041 Uiso 1 1 calc R . .
C18A C 0.40834(10) 0.40464(10) 0.57163(10) 0.0289(4) Uani 1 1 d . . .
C19A C 0.48428(8) 0.25726(8) 0.40475(8) 0.0186(3) Uani 1 1 d . . .
N5A N 0.5251(4) 0.2286(6) 0.4457(7) 0.0132(15) Uani 0.50 1 d PDU A 1
H5A H 0.5159 0.2273 0.4855 0.016 Uiso 0.50 1 calc PR A 1
C20A C 0.5836(3) 0.2001(3) 0.4238(4) 0.0188(15) Uani 0.50 1 d PDU A 1
H20A H 0.5782 0.1862 0.3796 0.023 Uiso 0.50 1 calc PR A 1
C21A C 0.5976(2) 0.1405(2) 0.4630(3) 0.0309(10) Uani 0.50 1 d PDU A 1
H21A H 0.6022 0.1535 0.5065 0.046 Uiso 0.50 1 calc PR A 1
H21B H 0.6362 0.1202 0.4486 0.046 Uiso 0.50 1 calc PR A 1
H21C H 0.5633 0.1093 0.4593 0.046 Uiso 0.50 1 calc PR A 1
C22A C 0.6355(3) 0.2508(3) 0.4270(3) 0.0303(12) Uani 0.50 1 d PDU A 1
H22A H 0.6253 0.2875 0.3998 0.045 Uiso 0.50 1 calc PR A 1
H22B H 0.6748 0.2311 0.4136 0.045 Uiso 0.50 1 calc PR A 1
H22C H 0.6397 0.2663 0.4699 0.045 Uiso 0.50 1 calc PR A 1
N5A' N 0.5199(6) 0.2201(9) 0.4408(18) 0.018(3) Uani 0.30 1 d PDU A 2
H5A' H 0.5094 0.2167 0.4801 0.022 Uiso 0.30 1 calc PR A 2
C20' C 0.5752(6) 0.1845(5) 0.4201(8) 0.024(3) Uani 0.30 1 d PDU A 2
H20' H 0.5860 0.1994 0.3773 0.028 Uiso 0.30 1 calc PR A 2
C21' C 0.5599(4) 0.1130(4) 0.4177(5) 0.0382(19) Uani 0.30 1 d PDU A 2
H21D H 0.5498 0.0975 0.4595 0.057 Uiso 0.30 1 calc PR A 2
H21E H 0.5959 0.0889 0.4018 0.057 Uiso 0.30 1 calc PR A 2
H21F H 0.5242 0.1061 0.3902 0.057 Uiso 0.30 1 calc PR A 2
C22' C 0.6298(4) 0.1999(5) 0.4628(4) 0.0435(19) Uani 0.30 1 d PDU A 2
H22D H 0.6386 0.2467 0.4615 0.065 Uiso 0.30 1 calc PR A 2
H22E H 0.6666 0.1757 0.4490 0.065 Uiso 0.30 1 calc PR A 2
H22F H 0.6193 0.1872 0.5054 0.065 Uiso 0.30 1 calc PR A 2
N5A" N 0.5232(9) 0.2260(11) 0.436(2) 0.024(5) Uani 0.20 1 d PDU A 3
H5A" H 0.5143 0.2227 0.4752 0.029 Uiso 0.20 1 calc PR A 3
C20" C 0.5811(9) 0.1937(8) 0.4173(11) 0.027(5) Uani 0.20 1 d PDU A 3
H20" H 0.5836 0.1928 0.3710 0.033 Uiso 0.20 1 calc PR A 3
C21" C 0.5809(7) 0.1244(6) 0.4410(8) 0.034(3) Uani 0.20 1 d PDU A 3
H21G H 0.5816 0.1246 0.4865 0.051 Uiso 0.20 1 calc PR A 3
H21H H 0.6177 0.1015 0.4253 0.051 Uiso 0.20 1 calc PR A 3
H21I H 0.5432 0.1022 0.4265 0.051 Uiso 0.20 1 calc PR A 3
C22" C 0.6364(8) 0.2323(7) 0.4423(8) 0.033(3) Uani 0.20 1 d PDU A 3
H22G H 0.6346 0.2770 0.4264 0.049 Uiso 0.20 1 calc PR A 3
H22H H 0.6752 0.2118 0.4288 0.049 Uiso 0.20 1 calc PR A 3
H22I H 0.6348 0.2331 0.4878 0.049 Uiso 0.20 1 calc PR A 3
Cl1A Cl 0.47331(3) 0.08733(3) 0.25466(3) 0.04656(16) Uani 1 1 d . . .
F1A F 0.1839(4) 0.0540(2) 0.1903(4) 0.0577(17) Uani 0.70(2) 1 d PDU B 1
F2A F 0.1695(3) 0.1570(3) 0.1962(3) 0.0455(12) Uani 0.70(2) 1 d PDU B 1
F3A F 0.2339(2) 0.1161(4) 0.1291(2) 0.0523(13) Uani 0.70(2) 1 d PDU B 1
F1A' F 0.1682(6) 0.0681(8) 0.2095(7) 0.058(3) Uani 0.30(2) 1 d PDU B 2
F2A' F 0.1842(7) 0.1683(5) 0.1800(7) 0.046(3) Uani 0.30(2) 1 d PDU B 2
F3A' F 0.2280(6) 0.0932(8) 0.1341(6) 0.057(3) Uani 0.30(2) 1 d PDU B 2
F4A F 0.4094(3) 0.4688(2) 0.5517(2) 0.0460(12) Uani 0.50 1 d PDU B 1
F5A F 0.36488(19) 0.4045(2) 0.6150(2) 0.0446(10) Uani 0.50 1 d PDU B 1
F6A F 0.4624(3) 0.3940(3) 0.5974(3) 0.0412(14) Uani 0.50 1 d PDU B 1
F4A' F 0.3863(3) 0.4624(3) 0.5651(4) 0.0455(17) Uani 0.35 1 d PDU B 2
F5A' F 0.3844(4) 0.3799(4) 0.6249(3) 0.0519(16) Uani 0.35 1 d PDU B 2
F6A' F 0.4699(3) 0.4105(4) 0.5836(4) 0.0342(17) Uani 0.35 1 d PDU B 2
F4A" F 0.3618(5) 0.4400(7) 0.5868(6) 0.042(3) Uani 0.15 1 d PDU B 3
F5A" F 0.4246(8) 0.3672(5) 0.6196(5) 0.051(3) Uani 0.15 1 d PDU B 3
F6A" F 0.4557(6) 0.4424(7) 0.5554(6) 0.056(3) Uani 0.15 1 d PDU B 3
N1A N 0.34821(8) -0.00125(8) 0.35971(8) 0.0272(4) Uani 1 1 d . . .
N2A N 0.33735(7) 0.08601(7) 0.29176(7) 0.0208(3) Uani 1 1 d . . .
N3A N 0.29500(8) 0.06390(7) 0.25074(7) 0.0236(3) Uani 1 1 d . B .
N4A N 0.35257(7) 0.24711(7) 0.36139(7) 0.0184(3) Uani 1 1 d . B .
H4A1 H 0.3307 0.2667 0.3324 0.022 Uiso 1 1 calc R . .
O1A O 0.40569(7) 0.15374(6) 0.38354(6) 0.0267(3) Uani 1 1 d . B .
O2A O 0.49346(6) 0.26461(6) 0.34864(6) 0.0226(3) Uani 1 1 d . A .
C1B C 0.35315(10) 0.32012(12) 0.07404(10) 0.0337(5) Uani 1 1 d . . .
C2B C 0.31604(11) 0.35394(15) 0.03171(11) 0.0448(6) Uani 1 1 d . . .
H2B H 0.2729 0.3447 0.0283 0.054 Uiso 1 1 calc R . .
C3B C 0.34289(12) 0.40031(16) -0.00447(11) 0.0508(7) Uani 1 1 d . . .
H3B H 0.3186 0.4244 -0.0332 0.061 Uiso 1 1 calc R . .
C4B C 0.40629(12) 0.41197(14) 0.00114(11) 0.0445(6) Uani 1 1 d . . .
H4B H 0.4246 0.4439 -0.0250 0.053 Uiso 1 1 calc R . .
C5B C 0.41550(9) 0.33659(10) 0.07709(9) 0.0259(4) Uani 1 1 d . C .
C6B C 0.53182(9) 0.24613(9) 0.14711(9) 0.0223(4) Uani 1 1 d . C .
C7B C 0.58675(10) 0.20223(10) 0.13984(10) 0.0296(4) Uani 1 1 d . . .
C8B C 0.50781(9) 0.27192(9) 0.20232(8) 0.0214(4) Uani 1 1 d . . .
H8B H 0.5219 0.2645 0.2435 0.026 Uiso 1 1 calc R C .
C9B C 0.45900(8) 0.31059(8) 0.18316(8) 0.0184(3) Uani 1 1 d . C .
C10B C 0.42013(8) 0.36001(8) 0.21597(8) 0.0176(3) Uani 1 1 d . . .
C11B C 0.39745(8) 0.40742(8) 0.31637(8) 0.0169(3) Uani 1 1 d . . .
C12B C 0.43689(8) 0.44100(8) 0.35721(8) 0.0190(3) Uani 1 1 d . C .
C13B C 0.41084(9) 0.48674(8) 0.39725(9) 0.0216(4) Uani 1 1 d . . .
H13B H 0.4366 0.5088 0.4263 0.026 Uiso 1 1 calc R C .
C14B C 0.34802(9) 0.50030(8) 0.39516(8) 0.0201(3) Uani 1 1 d . C .
C15B C 0.30911(8) 0.46902(8) 0.35284(8) 0.0188(3) Uani 1 1 d . . .
H15B H 0.2662 0.4798 0.3510 0.023 Uiso 1 1 calc R C .
C16B C 0.33360(8) 0.42197(8) 0.31339(8) 0.0164(3) Uani 1 1 d . C .
C17B C 0.50616(9) 0.42965(10) 0.35739(10) 0.0262(4) Uani 1 1 d . . .
H17D H 0.5147 0.3837 0.3663 0.039 Uiso 1 1 calc R C .
H17E H 0.5256 0.4569 0.3893 0.039 Uiso 1 1 calc R . .
H17F H 0.5234 0.4409 0.3167 0.039 Uiso 1 1 calc R . .
C18B C 0.31929(9) 0.54696(9) 0.44052(9) 0.0255(4) Uani 1 1 d . . .
C19B C 0.29010(8) 0.38359(8) 0.27288(8) 0.0170(3) Uani 1 1 d . . .
C20B C 0.20423(8) 0.38461(9) 0.19824(8) 0.0208(3) Uani 1 1 d . . .
H20B H 0.2246 0.3447 0.1811 0.025 Uiso 1 1 calc R C .
C21B C 0.18902(11) 0.42966(10) 0.14461(10) 0.0337(5) Uani 1 1 d . C .
H21J H 0.1676 0.4684 0.1604 0.051 Uiso 1 1 calc R . .
H21K H 0.1620 0.4070 0.1150 0.051 Uiso 1 1 calc R . .
H21L H 0.2276 0.4427 0.1238 0.051 Uiso 1 1 calc R . .
C22B C 0.14647(10) 0.36374(12) 0.23404(10) 0.0342(5) Uani 1 1 d . C .
H22J H 0.1588 0.3364 0.2693 0.051 Uiso 1 1 calc R . .
H22K H 0.1189 0.3390 0.2066 0.051 Uiso 1 1 calc R . .
H22L H 0.1246 0.4024 0.2493 0.051 Uiso 1 1 calc R . .
Cl1B Cl 0.32223(3) 0.26113(3) 0.12127(3) 0.04187(15) Uani 1 1 d . . .
F1B F 0.5911(2) 0.1824(3) 0.07908(19) 0.0340(10) Uani 0.40 1 d PDU C 1
F2B F 0.5813(3) 0.1488(3) 0.1726(3) 0.0314(11) Uani 0.40 1 d PDU C 1
F3B F 0.6384(2) 0.2308(2) 0.1538(3) 0.0330(10) Uani 0.40 1 d PDU C 1
F1B' F 0.5758(3) 0.1413(3) 0.1481(3) 0.0472(15) Uani 0.40 1 d PDU C 2
F2B' F 0.6336(3) 0.2177(3) 0.1832(3) 0.0612(16) Uani 0.40 1 d PDU C 2
F3B' F 0.6161(2) 0.2094(3) 0.0860(2) 0.0490(12) Uani 0.40 1 d PDU C 2
F1B" F 0.6363(5) 0.2355(5) 0.1270(6) 0.045(3) Uani 0.20 1 d PDU C 3
F2B" F 0.5961(5) 0.1682(5) 0.1914(4) 0.051(3) Uani 0.20 1 d PDU C 3
F3B" F 0.5778(5) 0.1591(5) 0.0940(5) 0.054(3) Uani 0.20 1 d PDU C 3
F4B F 0.28680(6) 0.59403(6) 0.41231(6) 0.0329(3) Uani 1 1 d U C .
F5B F 0.27883(6) 0.51627(6) 0.47862(6) 0.0358(3) Uani 1 1 d U C .
F6B F 0.36090(6) 0.57588(6) 0.47718(6) 0.0401(3) Uani 1 1 d U C .
N1B N 0.44232(8) 0.38102(10) 0.04095(8) 0.0324(4) Uani 1 1 d . . .
N2B N 0.45640(7) 0.30532(8) 0.12014(7) 0.0207(3) Uani 1 1 d . . .
N3B N 0.50127(7) 0.26626(8) 0.09712(7) 0.0231(3) Uani 1 1 d . C .
N4B N 0.42476(7) 0.35863(7) 0.27834(7) 0.0173(3) Uani 1 1 d . C .
H4B1 H 0.4453 0.3266 0.2960 0.021 Uiso 1 1 calc R . .
N5B N 0.24879(7) 0.41707(7) 0.23976(7) 0.0191(3) Uani 1 1 d . C .
H5B H 0.2481 0.4598 0.2428 0.023 Uiso 1 1 calc R . .
O1B O 0.39005(6) 0.40023(6) 0.18691(6) 0.0227(3) Uani 1 1 d . C .
O2B O 0.29163(6) 0.32304(6) 0.27243(6) 0.0209(3) Uani 1 1 d . C .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds 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
C1A C5A 1.385(3) . ?
C1A C2A 1.391(3) . ?
C1A Cl1A 1.718(2) . ?
C2A C3A 1.380(4) . ?
C3A C4A 1.381(4) . ?
C4A N1A 1.323(3) . ?
C5A N1A 1.324(2) . ?
C5A N2A 1.433(2) . ?
C6A N3A 1.330(2) . ?
C6A C8A 1.397(3) . ?
C6A C7A 1.492(3) . ?
C7A F3A' 1.266(11) . ?
C7A F1A 1.316(4) . ?
C7A F2A 1.334(5) . ?
C7A F2A' 1.338(9) . ?
C7A F3A 1.359(5) . ?
C7A F1A' 1.369(9) . ?
C8A C9A 1.378(3) . ?
C9A N2A 1.368(2) . ?
C9A C10A 1.488(2) . ?
C10A O1A 1.219(2) . ?
C10A N4A 1.360(2) . ?
C11A C16A 1.400(2) . ?
C11A C12A 1.409(2) . ?
C11A N4A 1.417(2) . ?
C12A C13A 1.384(3) . ?
C12A C17A 1.510(3) . ?
C13A C14A 1.389(3) . ?
C14A C15A 1.385(3) . ?
C14A C18A 1.503(3) . ?
C15A C16A 1.395(2) . ?
C16A C19A 1.501(2) . ?
C18A F4A" 1.278(9) . ?
C18A F4A' 1.286(7) . ?
C18A F6A 1.306(6) . ?
C18A F5A 1.321(4) . ?
C18A F6A" 1.326(10) . ?
C18A F5A" 1.336(10) . ?
C18A F6A' 1.352(8) . ?
C18A F5A' 1.356(6) . ?
C18A F4A 1.386(5) . ?
C19A O2A 1.234(2) . ?
C19A N5A" 1.25(3) . ?
C19A N5A' 1.33(3) . ?
C19A N5A 1.376(12) . ?
N5A C20A 1.465(5) . ?
C20A C21A 1.518(5) . ?
C20A C22A 1.528(5) . ?
N5A' C20' 1.464(7) . ?
C20' C21' 1.507(8) . ?
C20' C22' 1.523(9) . ?
N5A" C20" 1.464(8) . ?
C20" C21" 1.512(9) . ?
C20" C22" 1.526(9) . ?
N2A N3A 1.347(2) . ?
C1B C5B 1.383(3) . ?
C1B C2B 1.396(3) . ?
C1B Cl1B 1.716(2) . ?
C2B C3B 1.360(4) . ?
C3B C4B 1.389(4) . ?
C4B N1B 1.319(3) . ?
C5B N1B 1.331(3) . ?
C5B N2B 1.430(2) . ?
C6B N3B 1.327(3) . ?
C6B C8B 1.401(2) . ?
C6B C7B 1.494(3) . ?
C7B F1B' 1.287(6) . ?
C7B F3B 1.291(5) . ?
C7B F1B" 1.295(10) . ?
C7B F2B 1.312(6) . ?
C7B F3B' 1.328(4) . ?
C7B F2B" 1.328(9) . ?
C7B F3B" 1.341(9) . ?
C7B F1B 1.374(4) . ?
C7B F2B' 1.409(5) . ?
C8B C9B 1.379(2) . ?
C9B N2B 1.363(2) . ?
C9B C10B 1.493(2) . ?
C10B O1B 1.222(2) . ?
C10B N4B 1.348(2) . ?
C11B C12B 1.403(2) . ?
C11B C16B 1.406(2) . ?
C11B N4B 1.421(2) . ?
C12B C13B 1.393(2) . ?
C12B C17B 1.507(3) . ?
C13B C14B 1.379(3) . ?
C14B C15B 1.394(3) . ?
C14B C18B 1.502(2) . ?
C15B C16B 1.391(2) . ?
C16B C19B 1.502(2) . ?
C18B F6B 1.333(2) . ?
C18B F4B 1.339(2) . ?
C18B F5B 1.352(2) . ?
C19B O2B 1.245(2) . ?
C19B N5B 1.331(2) . ?
C20B N5B 1.470(2) . ?
C20B C21B 1.516(3) . ?
C20B C22B 1.523(3) . ?
N2B N3B 1.349(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
C5A C1A C2A 118.2(2) . . ?
C5A C1A Cl1A 121.18(16) . . ?
C2A C1A Cl1A 120.60(17) . . ?
C3A C2A C1A 118.1(2) . . ?
C2A C3A C4A 119.16(19) . . ?
N1A C4A C3A 123.1(2) . . ?
N1A C5A C1A 123.59(18) . . ?
N1A C5A N2A 115.04(17) . . ?
C1A C5A N2A 121.31(17) . . ?
N3A C6A C8A 113.06(16) . . ?
N3A C6A C7A 118.86(17) . . ?
C8A C6A C7A 128.08(18) . . ?
F3A' C7A F1A 84.5(6) . . ?
F3A' C7A F2A 120.6(6) . . ?
F1A C7A F2A 108.0(3) . . ?
F3A' C7A F2A' 104.6(6) . . ?
F1A C7A F2A' 125.4(5) . . ?
F2A C7A F2A' 22.7(6) . . ?
F3A' C7A F3A 21.5(6) . . ?
F1A C7A F3A 105.2(3) . . ?
F2A C7A F3A 107.5(3) . . ?
F2A' C7A F3A 87.7(6) . . ?
F3A' C7A F1A' 108.2(6) . . ?
F1A C7A F1A' 26.1(5) . . ?
F2A C7A F1A' 86.4(6) . . ?
F2A' C7A F1A' 107.4(6) . . ?
F3A C7A F1A' 127.1(5) . . ?
F3A' C7A C6A 116.0(6) . . ?
F1A C7A C6A 113.3(2) . . ?
F2A C7A C6A 111.2(2) . . ?
F2A' C7A C6A 110.2(5) . . ?
F3A C7A C6A 111.3(3) . . ?
F1A' C7A C6A 110.0(5) . . ?
C9A C8A C6A 104.08(16) . . ?
N2A C9A C8A 106.57(15) . . ?
N2A C9A C10A 120.69(15) . . ?
C8A C9A C10A 132.09(16) . . ?
O1A C10A N4A 124.42(16) . . ?
O1A C10A C9A 121.59(16) . . ?
N4A C10A C9A 113.81(15) . . ?
C16A C11A C12A 120.40(15) . . ?
C16A C11A N4A 122.87(15) . . ?
C12A C11A N4A 116.73(15) . . ?
C13A C12A C11A 118.93(16) . . ?
C13A C12A C17A 120.12(16) . . ?
C11A C12A C17A 120.92(16) . . ?
C12A C13A C14A 120.83(17) . . ?
C15A C14A C13A 120.23(16) . . ?
C15A C14A C18A 120.22(17) . . ?
C13A C14A C18A 119.54(17) . . ?
C14A C15A C16A 120.24(16) . . ?
C15A C16A C11A 119.30(16) . . ?
C15A C16A C19A 117.53(15) . . ?
C11A C16A C19A 123.01(15) . . ?
F4A" C18A F4A' 38.3(6) . . ?
F4A" C18A F6A 133.0(6) . . ?
F4A' C18A F6A 121.9(4) . . ?
F4A" C18A F5A 42.9(6) . . ?
F4A' C18A F5A 79.6(4) . . ?
F6A C18A F5A 109.1(4) . . ?
F4A" C18A F6A" 109.6(8) . . ?
F4A' C18A F6A" 73.4(7) . . ?
F6A C18A F6A" 61.8(7) . . ?
F5A C18A F6A" 136.9(5) . . ?
F4A" C18A F5A" 109.5(8) . . ?
F4A' C18A F5A" 135.5(6) . . ?
F6A C18A F5A" 48.8(7) . . ?
F5A C18A F5A" 68.6(6) . . ?
F6A" C18A F5A" 109.8(8) . . ?
F4A" C18A F6A' 131.7(6) . . ?
F4A' C18A F6A' 107.4(5) . . ?
F6A C18A F6A' 20.6(4) . . ?
F5A C18A F6A' 123.8(4) . . ?
F6A" C18A F6A' 41.3(7) . . ?
F5A" C18A F6A' 69.3(7) . . ?
F4A" C18A F5A' 72.5(7) . . ?
F4A' C18A F5A' 107.4(5) . . ?
F6A C18A F5A' 85.1(4) . . ?
F5A C18A F5A' 29.8(3) . . ?
F6A" C18A F5A' 137.1(6) . . ?
F5A" C18A F5A' 39.5(6) . . ?
F6A' C18A F5A' 104.0(5) . . ?
F4A" C18A F4A 63.4(7) . . ?
F4A' C18A F4A 25.1(3) . . ?
F6A C18A F4A 106.0(3) . . ?
F5A C18A F4A 103.5(3) . . ?
F6A" C18A F4A 49.5(7) . . ?
F5A" C18A F4A 141.6(5) . . ?
F6A' C18A F4A 87.7(4) . . ?
F5A' C18A F4A 128.7(4) . . ?
F4A" C18A C14A 112.7(5) . . ?
F4A' C18A C14A 113.3(4) . . ?
F6A C18A C14A 113.8(3) . . ?
F5A C18A C14A 114.1(2) . . ?
F6A" C18A C14A 107.4(5) . . ?
F5A" C18A C14A 107.9(5) . . ?
F6A' C18A C14A 113.2(4) . . ?
F5A' C18A C14A 110.9(3) . . ?
F4A C18A C14A 109.5(2) . . ?
O2A C19A N5A" 118.5(18) . . ?
O2A C19A N5A' 123.3(14) . . ?
N5A" C19A N5A' 7(2) . . ?
O2A C19A N5A 125.4(6) . . ?
N5A" C19A N5A 8(2) . . ?
N5A' C19A N5A 9.6(11) . . ?
O2A C19A C16A 121.72(15) . . ?
N5A" C19A C16A 119.7(18) . . ?
N5A' C19A C16A 114.9(14) . . ?
N5A C19A C16A 112.4(5) . . ?
C19A N5A C20A 120.7(10) . . ?
N5A C20A C21A 108.2(6) . . ?
N5A C20A C22A 109.8(6) . . ?
C21A C20A C22A 112.3(5) . . ?
C19A N5A' C20' 125(3) . . ?
N5A' C20' C21' 108.7(9) . . ?
N5A' C20' C22' 109.7(10) . . ?
C21' C20' C22' 113.0(9) . . ?
C19A N5A" C20" 132(3) . . ?
N5A" C20" C21" 109.5(11) . . ?
N5A" C20" C22" 109.4(11) . . ?
C21" C20" C22" 112.0(11) . . ?
C4A N1A C5A 117.79(19) . . ?
N3A N2A C9A 112.35(14) . . ?
N3A N2A C5A 117.44(14) . . ?
C9A N2A C5A 130.03(15) . . ?
C6A N3A N2A 103.92(14) . . ?
C10A N4A C11A 124.52(15) . . ?
C5B C1B C2B 117.5(2) . . ?
C5B C1B Cl1B 121.29(18) . . ?
C2B C1B Cl1B 121.17(18) . . ?
C3B C2B C1B 118.7(2) . . ?
C2B C3B C4B 119.2(2) . . ?
N1B C4B C3B 123.3(2) . . ?
N1B C5B C1B 124.01(19) . . ?
N1B C5B N2B 114.92(17) . . ?
C1B C5B N2B 121.07(19) . . ?
N3B C6B C8B 112.89(16) . . ?
N3B C6B C7B 119.59(17) . . ?
C8B C6B C7B 127.49(18) . . ?
F1B' C7B F3B 124.6(4) . . ?
F1B' C7B F1B" 134.0(6) . . ?
F3B C7B F1B" 26.3(4) . . ?
F1B' C7B F2B 25.0(3) . . ?
F3B C7B F2B 109.4(4) . . ?
F1B" C7B F2B 129.1(6) . . ?
F1B' C7B F3B' 108.4(4) . . ?
F3B C7B F3B' 75.3(4) . . ?
F1B" C7B F3B' 50.6(5) . . ?
F2B C7B F3B' 127.3(4) . . ?
F1B' C7B F2B" 53.1(5) . . ?
F3B C7B F2B" 85.1(5) . . ?
F1B" C7B F2B" 109.4(7) . . ?
F2B C7B F2B" 28.6(5) . . ?
F3B' C7B F2B" 135.8(5) . . ?
F1B' C7B F3B" 55.4(5) . . ?
F3B C7B F3B" 126.6(6) . . ?
F1B" C7B F3B" 108.0(7) . . ?
F2B C7B F3B" 80.2(5) . . ?
F3B' C7B F3B" 59.9(5) . . ?
F2B" C7B F3B" 106.9(7) . . ?
F1B' C7B F1B 81.7(3) . . ?
F3B C7B F1B 107.4(4) . . ?
F1B" C7B F1B 84.1(6) . . ?
F2B C7B F1B 105.7(3) . . ?
F3B' C7B F1B 33.8(3) . . ?
F2B" C7B F1B 129.1(5) . . ?
F3B" C7B F1B 27.4(5) . . ?
F1B' C7B F2B' 105.0(4) . . ?
F3B C7B F2B' 29.4(3) . . ?
F1B" C7B F2B' 55.6(5) . . ?
F2B C7B F2B' 84.0(4) . . ?
F3B' C7B F2B' 102.4(4) . . ?
F2B" C7B F2B' 57.1(5) . . ?
F3B" C7B F2B' 137.6(5) . . ?
F1B C7B F2B' 130.5(3) . . ?
F1B' C7B C6B 115.4(3) . . ?
F3B C7B C6B 112.3(3) . . ?
F1B" C7B C6B 110.6(5) . . ?
F2B C7B C6B 112.3(3) . . ?
F3B' C7B C6B 113.6(2) . . ?
F2B" C7B C6B 110.4(4) . . ?
F3B" C7B C6B 111.3(5) . . ?
F1B C7B C6B 109.4(2) . . ?
F2B' C7B C6B 111.0(3) . . ?
C9B C8B C6B 104.12(16) . . ?
N2B C9B C8B 106.47(15) . . ?
N2B C9B C10B 120.19(15) . . ?
C8B C9B C10B 132.51(16) . . ?
O1B C10B N4B 124.34(16) . . ?
O1B C10B C9B 120.90(16) . . ?
N4B C10B C9B 114.62(15) . . ?
C12B C11B C16B 120.90(15) . . ?
C12B C11B N4B 117.32(15) . . ?
C16B C11B N4B 121.78(15) . . ?
C13B C12B C11B 118.52(16) . . ?
C13B C12B C17B 119.98(16) . . ?
C11B C12B C17B 121.49(16) . . ?
C14B C13B C12B 120.61(16) . . ?
C13B C14B C15B 121.02(16) . . ?
C13B C14B C18B 120.66(16) . . ?
C15B C14B C18B 118.26(16) . . ?
C16B C15B C14B 119.56(16) . . ?
C15B C16B C11B 119.30(16) . . ?
C15B C16B C19B 118.98(15) . . ?
C11B C16B C19B 121.48(15) . . ?
F6B C18B F4B 107.27(15) . . ?
F6B C18B F5B 106.25(16) . . ?
F4B C18B F5B 106.09(15) . . ?
F6B C18B C14B 113.24(16) . . ?
F4B C18B C14B 112.34(16) . . ?
F5B C18B C14B 111.20(15) . . ?
O2B C19B N5B 122.02(16) . . ?
O2B C19B C16B 120.84(15) . . ?
N5B C19B C16B 117.09(14) . . ?
N5B C20B C21B 109.09(15) . . ?
N5B C20B C22B 110.51(15) . . ?
C21B C20B C22B 112.46(17) . . ?
C4B N1B C5B 117.2(2) . . ?
N3B N2B C9B 112.60(15) . . ?
N3B N2B C5B 117.91(14) . . ?
C9B N2B C5B 129.44(15) . . ?
C6B N3B N2B 103.91(14) . . ?
C10B N4B C11B 121.96(14) . . ?
C19B N5B C20B 121.74(14) . . ?

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
C5A C1A C2A C3A 1.5(3) . . . . ?
Cl1A C1A C2A C3A -178.93(16) . . . . ?
C1A C2A C3A C4A 0.1(3) . . . . ?
C2A C3A C4A N1A -1.2(3) . . . . ?
C2A C1A C5A N1A -2.2(3) . . . . ?
Cl1A C1A C5A N1A 178.24(15) . . . . ?
C2A C1A C5A N2A -179.14(17) . . . . ?
Cl1A C1A C5A N2A 1.3(3) . . . . ?
N3A C6A C7A F3A' -64.7(10) . . . . ?
C8A C6A C7A F3A' 116.1(10) . . . . ?
N3A C6A C7A F1A 30.6(6) . . . . ?
C8A C6A C7A F1A -148.6(6) . . . . ?
N3A C6A C7A F2A 152.5(5) . . . . ?
C8A C6A C7A F2A -26.7(5) . . . . ?
N3A C6A C7A F2A' 176.8(10) . . . . ?
C8A C6A C7A F2A' -2.4(10) . . . . ?
N3A C6A C7A F3A -87.7(5) . . . . ?
C8A C6A C7A F3A 93.1(5) . . . . ?
N3A C6A C7A F1A' 58.5(10) . . . . ?
C8A C6A C7A F1A' -120.7(10) . . . . ?
N3A C6A C8A C9A 0.7(2) . . . . ?
C7A C6A C8A C9A 179.9(2) . . . . ?
C6A C8A C9A N2A -0.1(2) . . . . ?
C6A C8A C9A C10A -170.6(2) . . . . ?
N2A C9A C10A O1A 3.3(3) . . . . ?
C8A C9A C10A O1A 172.8(2) . . . . ?
N2A C9A C10A N4A -172.02(17) . . . . ?
C8A C9A C10A N4A -2.6(3) . . . . ?
C16A C11A C12A C13A 2.8(3) . . . . ?
N4A C11A C12A C13A -176.92(16) . . . . ?
C16A C11A C12A C17A -175.20(17) . . . . ?
N4A C11A C12A C17A 5.0(2) . . . . ?
C11A C12A C13A C14A -1.6(3) . . . . ?
C17A C12A C13A C14A 176.43(17) . . . . ?
C12A C13A C14A C15A -0.8(3) . . . . ?
C12A C13A C14A C18A 178.47(17) . . . . ?
C13A C14A C15A C16A 2.1(3) . . . . ?
C18A C14A C15A C16A -177.21(17) . . . . ?
C14A C15A C16A C11A -0.9(3) . . . . ?
C14A C15A C16A C19A 174.69(16) . . . . ?
C12A C11A C16A C15A -1.6(2) . . . . ?
N4A C11A C16A C15A 178.14(16) . . . . ?
C12A C11A C16A C19A -176.90(16) . . . . ?
N4A C11A C16A C19A 2.8(3) . . . . ?
C15A C14A C18A F4A" 170.0(8) . . . . ?
C13A C14A C18A F4A" -9.3(8) . . . . ?
C15A C14A C18A F4A' 128.2(5) . . . . ?
C13A C14A C18A F4A' -51.1(5) . . . . ?
C15A C14A C18A F6A -16.9(4) . . . . ?
C13A C14A C18A F6A 163.8(3) . . . . ?
C15A C14A C18A F5A -143.1(3) . . . . ?
C13A C14A C18A F5A 37.6(4) . . . . ?
C15A C14A C18A F6A" 49.2(8) . . . . ?
C13A C14A C18A F6A" -130.1(8) . . . . ?
C15A C14A C18A F5A" -69.1(8) . . . . ?
C13A C14A C18A F5A" 111.6(8) . . . . ?
C15A C14A C18A F6A' 5.5(5) . . . . ?
C13A C14A C18A F6A' -173.7(4) . . . . ?
C15A C14A C18A F5A' -110.9(5) . . . . ?
C13A C14A C18A F5A' 69.8(5) . . . . ?
C15A C14A C18A F4A 101.5(3) . . . . ?
C13A C14A C18A F4A -77.8(3) . . . . ?
C15A C16A C19A O2A -125.87(18) . . . . ?
C11A C16A C19A O2A 49.5(3) . . . . ?
C15A C16A C19A N5A" 50.5(14) . . . . ?
C11A C16A C19A N5A" -134.1(14) . . . . ?
C15A C16A C19A N5A' 56.3(9) . . . . ?
C11A C16A C19A N5A' -128.3(9) . . . . ?
C15A C16A C19A N5A 46.2(6) . . . . ?
C11A C16A C19A N5A -138.4(6) . . . . ?
O2A C19A N5A C20A -3.7(12) . . . . ?
N5A" C19A N5A C20A 32(10) . . . . ?
N5A' C19A N5A C20A 78(10) . . . . ?
C16A C19A N5A C20A -175.4(6) . . . . ?
C19A N5A C20A C21A -145.0(9) . . . . ?
C19A N5A C20A C22A 92.1(10) . . . . ?
O2A C19A N5A' C20' 1.7(19) . . . . ?
N5A" C19A N5A' C20' -46(20) . . . . ?
N5A C19A N5A' C20' -103(11) . . . . ?
C16A C19A N5A' C20' 179.5(10) . . . . ?
C19A N5A' C20' C21' -107.2(16) . . . . ?
C19A N5A' C20' C22' 128.8(15) . . . . ?
O2A C19A N5A" C20" -1(3) . . . . ?
N5A' C19A N5A" C20" 135(22) . . . . ?
N5A C19A N5A" C20" -148(12) . . . . ?
C16A C19A N5A" C20" -177.0(16) . . . . ?
C19A N5A" C20" C21" -129(3) . . . . ?
C19A N5A" C20" C22" 108(3) . . . . ?
C3A C4A N1A C5A 0.7(3) . . . . ?
C1A C5A N1A C4A 1.1(3) . . . . ?
N2A C5A N1A C4A 178.22(17) . . . . ?
C8A C9A N2A N3A -0.6(2) . . . . ?
C10A C9A N2A N3A 171.26(16) . . . . ?
C8A C9A N2A C5A -175.57(19) . . . . ?
C10A C9A N2A C5A -3.7(3) . . . . ?
N1A C5A N2A N3A -67.6(2) . . . . ?
C1A C5A N2A N3A 109.5(2) . . . . ?
N1A C5A N2A C9A 107.2(2) . . . . ?
C1A C5A N2A C9A -75.7(3) . . . . ?
C8A C6A N3A N2A -1.0(2) . . . . ?
C7A C6A N3A N2A 179.68(19) . . . . ?
C9A N2A N3A C6A 1.0(2) . . . . ?
C5A N2A N3A C6A 176.64(17) . . . . ?
O1A C10A N4A C11A -11.0(3) . . . . ?
C9A C10A N4A C11A 164.19(16) . . . . ?
C16A C11A N4A C10A 51.8(3) . . . . ?
C12A C11A N4A C10A -128.47(19) . . . . ?
C5B C1B C2B C3B 0.7(3) . . . . ?
Cl1B C1B C2B C3B 179.8(2) . . . . ?
C1B C2B C3B C4B 0.9(4) . . . . ?
C2B C3B C4B N1B -1.3(4) . . . . ?
C2B C1B C5B N1B -2.2(3) . . . . ?
Cl1B C1B C5B N1B 178.73(16) . . . . ?
C2B C1B C5B N2B 178.61(19) . . . . ?
Cl1B C1B C5B N2B -0.5(3) . . . . ?
N3B C6B C7B F1B' -98.3(4) . . . . ?
C8B C6B C7B F1B' 83.8(4) . . . . ?
N3B C6B C7B F3B 110.8(4) . . . . ?
C8B C6B C7B F3B -67.2(4) . . . . ?
N3B C6B C7B F1B" 82.5(6) . . . . ?
C8B C6B C7B F1B" -95.4(6) . . . . ?
N3B C6B C7B F2B -125.5(3) . . . . ?
C8B C6B C7B F2B 56.6(4) . . . . ?
N3B C6B C7B F3B' 27.7(4) . . . . ?
C8B C6B C7B F3B' -150.2(4) . . . . ?
N3B C6B C7B F2B" -156.2(6) . . . . ?
C8B C6B C7B F2B" 25.9(6) . . . . ?
N3B C6B C7B F3B" -37.6(7) . . . . ?
C8B C6B C7B F3B" 144.5(6) . . . . ?
N3B C6B C7B F1B -8.4(4) . . . . ?
C8B C6B C7B F1B 173.7(3) . . . . ?
N3B C6B C7B F2B' 142.4(4) . . . . ?
C8B C6B C7B F2B' -35.5(4) . . . . ?
N3B C6B C8B C9B -0.1(2) . . . . ?
C7B C6B C8B C9B 177.96(19) . . . . ?
C6B C8B C9B N2B 0.6(2) . . . . ?
C6B C8B C9B C10B -168.59(18) . . . . ?
N2B C9B C10B O1B -6.9(3) . . . . ?
C8B C9B C10B O1B 161.12(19) . . . . ?
N2B C9B C10B N4B 177.29(16) . . . . ?
C8B C9B C10B N4B -14.7(3) . . . . ?
C16B C11B C12B C13B 3.4(3) . . . . ?
N4B C11B C12B C13B -176.79(15) . . . . ?
C16B C11B C12B C17B -175.15(17) . . . . ?
N4B C11B C12B C17B 4.6(2) . . . . ?
C11B C12B C13B C14B -2.3(3) . . . . ?
C17B C12B C13B C14B 176.32(17) . . . . ?
C12B C13B C14B C15B -0.4(3) . . . . ?
C12B C13B C14B C18B 176.75(17) . . . . ?
C13B C14B C15B C16B 2.0(3) . . . . ?
C18B C14B C15B C16B -175.22(16) . . . . ?
C14B C15B C16B C11B -0.8(2) . . . . ?
C14B C15B C16B C19B 173.49(15) . . . . ?
C12B C11B C16B C15B -1.9(2) . . . . ?
N4B C11B C16B C15B 178.34(15) . . . . ?
C12B C11B C16B C19B -176.07(15) . . . . ?
N4B C11B C16B C19B 4.2(2) . . . . ?
C13B C14B C18B F6B 5.2(3) . . . . ?
C15B C14B C18B F6B -177.63(16) . . . . ?
C13B C14B C18B F4B 126.87(19) . . . . ?
C15B C14B C18B F4B -55.9(2) . . . . ?
C13B C14B C18B F5B -114.39(19) . . . . ?
C15B C14B C18B F5B 62.8(2) . . . . ?
C15B C16B C19B O2B -127.89(18) . . . . ?
C11B C16B C19B O2B 46.3(2) . . . . ?
C15B C16B C19B N5B 49.6(2) . . . . ?
C11B C16B C19B N5B -136.18(17) . . . . ?
C3B C4B N1B C5B 0.0(4) . . . . ?
C1B C5B N1B C4B 1.8(3) . . . . ?
N2B C5B N1B C4B -178.94(19) . . . . ?
C8B C9B N2B N3B -1.0(2) . . . . ?
C10B C9B N2B N3B 169.83(15) . . . . ?
C8B C9B N2B C5B -178.29(18) . . . . ?
C10B C9B N2B C5B -7.5(3) . . . . ?
N1B C5B N2B N3B -66.9(2) . . . . ?
C1B C5B N2B N3B 112.3(2) . . . . ?
N1B C5B N2B C9B 110.3(2) . . . . ?
C1B C5B N2B C9B -70.4(3) . . . . ?
C8B C6B N3B N2B -0.5(2) . . . . ?
C7B C6B N3B N2B -178.69(17) . . . . ?
C9B N2B N3B C6B 0.9(2) . . . . ?
C5B N2B N3B C6B 178.56(16) . . . . ?
O1B C10B N4B C11B -4.0(3) . . . . ?
C9B C10B N4B C11B 171.66(15) . . . . ?
C12B C11B N4B C10B -123.54(18) . . . . ?
C16B C11B N4B C10B 56.2(2) . . . . ?
O2B C19B N5B C20B -2.9(3) . . . . ?
C16B C19B N5B C20B 179.59(15) . . . . ?
C21B C20B N5B C19B -150.02(17) . . . . ?
C22B C20B N5B C19B 85.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        29.62
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.119
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 993890'
#######################################################################
#
#                 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_mo_al263_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H20 F3 N O4'
_chemical_formula_weight         347.33

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'

_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                   21.2910(12)
_cell_length_b                   11.5227(6)
_cell_length_c                   14.4085(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.162(2)
_cell_angle_gamma                90.00
_cell_volume                     3411.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6938
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      29.44

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9769
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            20284
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         30.15
_reflns_number_total             4572
_reflns_number_gt                3451
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    'SHELXS-2012 (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2sigma(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)+(0.0668P)²+4.9675P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4572
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1497
_refine_ls_wR_factor_gt          0.1368
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
N1 N 0.37125(7) 0.46193(12) 0.41685(9) 0.0209(3) Uani 1 1 d . . .
O1 O 0.42692(7) 0.50386(12) 0.56917(9) 0.0314(3) Uani 1 1 d . . .
O2 O 0.35444(8) 0.70082(13) 0.57883(10) 0.0412(4) Uani 1 1 d . . .
O3 O 0.36152(6) 0.25246(11) 0.51693(8) 0.0246(3) Uani 1 1 d . . .
O4 O 0.46773(6) 0.22524(12) 0.53255(9) 0.0312(3) Uani 1 1 d . . .
C1 C 0.32640(8) 0.49834(14) 0.32831(11) 0.0201(3) Uani 1 1 d . . .
C2 C 0.26090(8) 0.46736(14) 0.30943(11) 0.0205(3) Uani 1 1 d . . .
C3 C 0.21987(8) 0.50266(14) 0.22067(11) 0.0213(3) Uani 1 1 d . . .
C4 C 0.24373(9) 0.56577(15) 0.15507(12) 0.0241(3) Uani 1 1 d . . .
H4 H 0.2152 0.5886 0.0955 0.029 Uiso 1 1 calc R . .
C5 C 0.30879(9) 0.59532(15) 0.17644(12) 0.0243(4) Uani 1 1 d . . .
H5 H 0.3247 0.6383 0.1312 0.029 Uiso 1 1 calc R . .
C6 C 0.35123(8) 0.56305(14) 0.26318(11) 0.0214(3) Uani 1 1 d . . .
C7 C 0.23506(9) 0.40120(17) 0.38217(12) 0.0275(4) Uani 1 1 d . . .
H7A H 0.2119 0.4546 0.4146 0.041 Uiso 1 1 calc R . .
H7B H 0.2714 0.3654 0.4297 0.041 Uiso 1 1 calc R . .
H7C H 0.2051 0.3406 0.3493 0.041 Uiso 1 1 calc R . .
C8 C 0.14787(9) 0.46940(15) 0.19352(12) 0.0250(4) Uani 1 1 d . . .
C9 C 0.42163(9) 0.59824(17) 0.28627(13) 0.0278(4) Uani 1 1 d . . .
H9A H 0.4286 0.6494 0.2355 0.042 Uiso 1 1 calc R . .
H9B H 0.4489 0.5289 0.2904 0.042 Uiso 1 1 calc R . .
H9C H 0.4333 0.6394 0.3479 0.042 Uiso 1 1 calc R . .
C10 C 0.38329(9) 0.52903(16) 0.49794(12) 0.0252(4) Uani 1 1 d . . .
C11 C 0.33802(11) 0.63256(17) 0.49488(14) 0.0347(4) Uani 1 1 d . . .
H11A H 0.3391 0.6819 0.4391 0.042 Uiso 1 1 calc R . .
H11B H 0.2929 0.6038 0.4851 0.042 Uiso 1 1 calc R . .
C12 C 0.40570(14) 0.7768(2) 0.58093(18) 0.0520(6) Uani 1 1 d . . .
H12A H 0.4449 0.7322 0.5807 0.078 Uiso 1 1 calc R . .
H12B H 0.4140 0.8242 0.6393 0.078 Uiso 1 1 calc R . .
H12C H 0.3943 0.8273 0.5243 0.078 Uiso 1 1 calc R . .
C13 C 0.41585(8) 0.36405(15) 0.41794(12) 0.0227(3) Uani 1 1 d . . .
H13 H 0.4615 0.3939 0.4324 0.027 Uiso 1 1 calc R . .
C14 C 0.40046(10) 0.29815(17) 0.32267(12) 0.0290(4) Uani 1 1 d . . .
H14A H 0.3556 0.2694 0.3077 0.043 Uiso 1 1 calc R . .
H14B H 0.4304 0.2325 0.3278 0.043 Uiso 1 1 calc R . .
H14C H 0.4054 0.3503 0.2713 0.043 Uiso 1 1 calc R . .
C15 C 0.41047(8) 0.27771(15) 0.49541(11) 0.0221(3) Uani 1 1 d . . .
C16 C 0.46647(10) 0.13448(19) 0.60120(14) 0.0355(4) Uani 1 1 d . . .
H16A H 0.4512 0.1664 0.6544 0.053 Uiso 1 1 calc R . .
H16B H 0.5104 0.1029 0.6261 0.053 Uiso 1 1 calc R . .
H16C H 0.4370 0.0726 0.5696 0.053 Uiso 1 1 calc R . .
F1 F 0.11708(5) 0.50612(11) 0.25706(9) 0.0356(3) Uani 1 1 d . . .
F2 F 0.11660(6) 0.51445(11) 0.10839(8) 0.0372(3) Uani 1 1 d . . .
F3 F 0.13997(6) 0.35430(10) 0.18597(9) 0.0388(3) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds 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
N1 C10 1.368(2) . ?
N1 C1 1.442(2) . ?
N1 C13 1.472(2) . ?
O1 C10 1.225(2) . ?
O2 C12 1.393(3) . ?
O2 C11 1.408(2) . ?
O3 C15 1.198(2) . ?
O4 C15 1.341(2) . ?
O4 C16 1.445(2) . ?
C1 C2 1.396(2) . ?
C1 C6 1.406(2) . ?
C2 C3 1.407(2) . ?
C2 C7 1.511(2) . ?
C3 C4 1.390(2) . ?
C3 C8 1.528(2) . ?
C4 C5 1.381(3) . ?
C5 C6 1.388(2) . ?
C6 C9 1.504(2) . ?
C8 F1 1.327(2) . ?
C8 F3 1.338(2) . ?
C8 F2 1.338(2) . ?
C10 C11 1.527(3) . ?
C13 C15 1.522(2) . ?
C13 C14 1.527(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
C10 N1 C1 121.61(15) . . ?
C10 N1 C13 116.60(14) . . ?
C1 N1 C13 120.57(13) . . ?
C12 O2 C11 112.75(17) . . ?
C15 O4 C16 114.96(14) . . ?
C2 C1 C6 122.46(15) . . ?
C2 C1 N1 119.66(14) . . ?
C6 C1 N1 117.87(15) . . ?
C1 C2 C3 117.02(15) . . ?
C1 C2 C7 121.35(15) . . ?
C3 C2 C7 121.61(15) . . ?
C4 C3 C2 121.26(16) . . ?
C4 C3 C8 118.54(14) . . ?
C2 C3 C8 120.18(15) . . ?
C5 C4 C3 120.08(15) . . ?
C4 C5 C6 120.90(15) . . ?
C5 C6 C1 118.26(15) . . ?
C5 C6 C9 120.23(15) . . ?
C1 C6 C9 121.50(15) . . ?
F1 C8 F3 107.34(15) . . ?
F1 C8 F2 106.96(15) . . ?
F3 C8 F2 106.76(14) . . ?
F1 C8 C3 112.76(14) . . ?
F3 C8 C3 111.45(15) . . ?
F2 C8 C3 111.26(15) . . ?
O1 C10 N1 120.87(17) . . ?
O1 C10 C11 122.93(16) . . ?
N1 C10 C11 116.17(15) . . ?
O2 C11 C10 113.49(16) . . ?
N1 C13 C15 109.67(13) . . ?
N1 C13 C14 112.65(14) . . ?
C15 C13 C14 107.13(14) . . ?
O3 C15 O4 123.30(16) . . ?
O3 C15 C13 125.87(15) . . ?
O4 C15 C13 110.64(14) . . ?

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 -90.5(2) . . . . ?
C13 N1 C1 C2 102.62(18) . . . . ?
C10 N1 C1 C6 90.5(2) . . . . ?
C13 N1 C1 C6 -76.4(2) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
N1 C1 C2 C3 -178.27(15) . . . . ?
C6 C1 C2 C7 -177.92(16) . . . . ?
N1 C1 C2 C7 3.1(2) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C7 C2 C3 C4 178.52(16) . . . . ?
C1 C2 C3 C8 178.39(15) . . . . ?
C7 C2 C3 C8 -2.9(2) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C8 C3 C4 C5 -178.72(16) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C5 C6 C9 -178.62(16) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
N1 C1 C6 C5 178.00(15) . . . . ?
C2 C1 C6 C9 178.27(16) . . . . ?
N1 C1 C6 C9 -2.7(2) . . . . ?
C4 C3 C8 F1 -123.91(17) . . . . ?
C2 C3 C8 F1 57.5(2) . . . . ?
C4 C3 C8 F3 115.29(17) . . . . ?
C2 C3 C8 F3 -63.3(2) . . . . ?
C4 C3 C8 F2 -3.7(2) . . . . ?
C2 C3 C8 F2 177.68(15) . . . . ?
C1 N1 C10 O1 -171.37(16) . . . . ?
C13 N1 C10 O1 -4.0(2) . . . . ?
C1 N1 C10 C11 10.8(2) . . . . ?
C13 N1 C10 C11 178.16(15) . . . . ?
C12 O2 C11 C10 79.9(2) . . . . ?
O1 C10 C11 O2 4.6(3) . . . . ?
N1 C10 C11 O2 -177.61(16) . . . . ?
C10 N1 C13 C15 63.60(18) . . . . ?
C1 N1 C13 C15 -128.86(15) . . . . ?
C10 N1 C13 C14 -177.18(15) . . . . ?
C1 N1 C13 C14 -9.6(2) . . . . ?
C16 O4 C15 O3 0.2(2) . . . . ?
C16 O4 C15 C13 -175.06(15) . . . . ?
N1 C13 C15 O3 36.8(2) . . . . ?
C14 C13 C15 O3 -85.7(2) . . . . ?
N1 C13 C15 O4 -148.10(14) . . . . ?
C14 C13 C15 O4 89.34(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.905
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.747
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 993891'
#######################################################################
#
#                 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_mo_al270_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H6 F3 N'
_chemical_formula_weight         197.16

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   4.7643(3)
_cell_length_b                   12.7324(9)
_cell_length_c                   13.8685(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     841.28(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9947
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      29.39

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9594
_exptl_absorpt_correction_T_max  0.9945
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            14820
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0128
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         29.94
_reflns_number_total             2258
_reflns_number_gt                2168
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    'SHELXS-2012 (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2sigma(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)+(0.0447P)²+0.1773P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_chemical_absolute_configuration ad
_refine_ls_abs_structure_Flack   0.1(5)
_refine_ls_number_reflns         2258
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0818
_refine_ls_wR_factor_gt          0.0805
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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
N1 N 0.5212(2) 0.79827(8) 0.37051(7) 0.0245(2) Uani 1 1 d . . .
C1 C 0.1880(2) 0.65889(9) 0.33893(8) 0.0175(2) Uani 1 1 d . . .
C2 C 0.3353(3) 0.72930(10) 0.40016(8) 0.0219(2) Uani 1 1 d . . .
H2 H 0.2965 0.7263 0.4673 0.026 Uiso 1 1 calc R . .
C3 C 0.5745(3) 0.80036(9) 0.27356(9) 0.0229(2) Uani 1 1 d . . .
H3 H 0.7094 0.8494 0.2507 0.027 Uiso 1 1 calc R . .
C4 C 0.4469(3) 0.73670(9) 0.20730(8) 0.0198(2) Uani 1 1 d . . .
H4 H 0.4924 0.7425 0.1408 0.024 Uiso 1 1 calc R . .
C5 C 0.2457(2) 0.66183(8) 0.23875(7) 0.0165(2) Uani 1 1 d . . .
C6 C 0.0993(2) 0.58976(9) 0.17837(7) 0.0175(2) Uani 1 1 d . . .
C7 C -0.0911(3) 0.52061(9) 0.21664(8) 0.0214(2) Uani 1 1 d . . .
H7 H -0.1872 0.4732 0.1753 0.026 Uiso 1 1 calc R . .
C8 C -0.1462(3) 0.51894(10) 0.31690(9) 0.0236(2) Uani 1 1 d . . .
H8 H -0.2784 0.4705 0.3425 0.028 Uiso 1 1 calc R . .
C9 C -0.0093(3) 0.58700(9) 0.37689(8) 0.0213(2) Uani 1 1 d . . .
H9 H -0.0467 0.5860 0.4442 0.026 Uiso 1 1 calc R . .
C10 C 0.1471(3) 0.59151(11) 0.07142(8) 0.0231(2) Uani 1 1 d . . .
F1 F 0.0602(2) 0.68210(7) 0.03178(5) 0.0350(2) Uani 1 1 d . . .
F2 F 0.41983(16) 0.58184(7) 0.04821(5) 0.02977(19) Uani 1 1 d . . .
F3 F 0.01144(19) 0.51418(7) 0.02539(5) 0.0336(2) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds 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
N1 C2 1.3134(17) . ?
N1 C3 1.3687(15) . ?
C1 C9 1.4137(16) . ?
C1 C5 1.4168(15) . ?
C1 C2 1.4201(16) . ?
C3 C4 1.3679(15) . ?
C4 C5 1.4202(16) . ?
C5 C6 1.4248(15) . ?
C6 C7 1.3709(16) . ?
C6 C10 1.5008(15) . ?
C7 C8 1.4152(16) . ?
C8 C9 1.3671(17) . ?
C10 F3 1.3396(15) . ?
C10 F1 1.3432(16) . ?
C10 F2 1.3443(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
C2 N1 C3 116.47(10) . . ?
C9 C1 C5 120.75(10) . . ?
C9 C1 C2 120.96(10) . . ?
C5 C1 C2 118.28(10) . . ?
N1 C2 C1 124.62(10) . . ?
C4 C3 N1 124.46(11) . . ?
C3 C4 C5 119.44(10) . . ?
C1 C5 C4 116.73(10) . . ?
C1 C5 C6 117.66(10) . . ?
C4 C5 C6 125.61(10) . . ?
C7 C6 C5 120.67(10) . . ?
C7 C6 C10 119.51(10) . . ?
C5 C6 C10 119.80(10) . . ?
C6 C7 C8 120.85(11) . . ?
C9 C8 C7 119.99(11) . . ?
C8 C9 C1 120.07(10) . . ?
F3 C10 F1 106.70(10) . . ?
F3 C10 F2 106.55(10) . . ?
F1 C10 F2 106.19(11) . . ?
F3 C10 C6 112.75(11) . . ?
F1 C10 C6 111.74(10) . . ?
F2 C10 C6 112.45(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
C3 N1 C2 C1 -0.48(18) . . . . ?
C9 C1 C2 N1 -179.96(11) . . . . ?
C5 C1 C2 N1 0.59(18) . . . . ?
C2 N1 C3 C4 0.44(18) . . . . ?
N1 C3 C4 C5 -0.51(18) . . . . ?
C9 C1 C5 C4 179.96(10) . . . . ?
C2 C1 C5 C4 -0.60(15) . . . . ?
C9 C1 C5 C6 -0.29(16) . . . . ?
C2 C1 C5 C6 179.15(10) . . . . ?
C3 C4 C5 C1 0.57(16) . . . . ?
C3 C4 C5 C6 -179.16(11) . . . . ?
C1 C5 C6 C7 0.24(15) . . . . ?
C4 C5 C6 C7 179.97(11) . . . . ?
C1 C5 C6 C10 178.41(10) . . . . ?
C4 C5 C6 C10 -1.87(16) . . . . ?
C5 C6 C7 C8 -0.16(17) . . . . ?
C10 C6 C7 C8 -178.33(11) . . . . ?
C6 C7 C8 C9 0.12(19) . . . . ?
C7 C8 C9 C1 -0.17(18) . . . . ?
C5 C1 C9 C8 0.26(17) . . . . ?
C2 C1 C9 C8 -179.17(11) . . . . ?
C7 C6 C10 F3 -6.60(16) . . . . ?
C5 C6 C10 F3 175.21(10) . . . . ?
C7 C6 C10 F1 113.58(13) . . . . ?
C5 C6 C10 F1 -64.60(13) . . . . ?
C7 C6 C10 F2 -127.10(12) . . . . ?
C5 C6 C10 F2 54.71(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.954
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.041
_database_code_depnum_ccdc_archive 'CCDC 993892'
