# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

#######################################################################
#
#                 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_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H28 F8 N4, 2(Br)'
_chemical_formula_sum            'C26 H28 Br2 F8 N4'
_chemical_formula_weight         708.34

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   C2

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

_cell_length_a                   13.0391(5)
_cell_length_b                   6.8246(3)
_cell_length_c                   15.9891(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.828(5)
_cell_angle_gamma                90.00
_cell_volume                     1421.08(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1201
_cell_measurement_theta_min      3.5680
_cell_measurement_theta_max      26.7250

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             708
_exptl_absorpt_coefficient_mu    2.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6678
_exptl_absorpt_correction_T_max  0.9173
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2711
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2013
_reflns_number_gt                1774
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_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)+(0.0587P)²+0.0000P] 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   0.015(15)
_refine_ls_number_reflns         2013
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.0967
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.54416(10) 0.2920(2) 0.26070(7) 0.0503(3) Uani 0.92 1 d P A 1
Br1B Br 0.5412(12) 0.288(4) 0.3024(10) 0.061(4) Uani 0.08 1 d P B 2
F9 F 0.3349(2) -0.1179(5) 0.1760(2) 0.0413(8) Uani 1 1 d . . .
F10 F 0.4958(2) -0.1163(5) 0.0825(2) 0.0395(8) Uani 1 1 d . . .
F12 F 0.4003(2) 0.5074(5) -0.0232(2) 0.0400(8) Uani 1 1 d . . .
F13 F 0.2460(2) 0.5153(5) 0.07758(19) 0.0384(7) Uani 1 1 d . . .
N1 N 0.2210(3) 0.2779(9) 0.2758(2) 0.0291(9) Uani 1 1 d . . .
N2 N 0.2543(5) 0.3940(9) 0.4272(3) 0.0559(15) Uani 1 1 d . . .
C1 C 0.1203(4) 0.2942(13) 0.3188(3) 0.0412(12) Uani 1 1 d . . .
H1A H 0.0839 0.1668 0.3167 0.049 Uiso 1 1 calc R . .
H1B H 0.0757 0.3937 0.2904 0.049 Uiso 1 1 calc R . .
C2 C 0.1453(6) 0.3545(12) 0.4105(4) 0.064(2) Uani 1 1 d . . .
H2A H 0.1055 0.4732 0.4233 0.077 Uiso 1 1 calc R . .
H2B H 0.1238 0.2482 0.4480 0.077 Uiso 1 1 calc R . .
C3 C 0.2854(6) 0.5425(10) 0.3677(4) 0.0546(18) Uani 1 1 d . . .
H3A H 0.3580 0.5782 0.3809 0.066 Uiso 1 1 calc R . .
H3B H 0.2433 0.6616 0.3745 0.066 Uiso 1 1 calc R . .
C4 C 0.2740(5) 0.4744(8) 0.2766(4) 0.0344(13) Uani 1 1 d . . .
H4A H 0.2327 0.5700 0.2427 0.041 Uiso 1 1 calc R . .
H4B H 0.3423 0.4626 0.2527 0.041 Uiso 1 1 calc R . .
C5 C 0.2883(5) 0.1331(9) 0.3241(4) 0.0384(14) Uani 1 1 d . . .
H5A H 0.3535 0.1144 0.2959 0.046 Uiso 1 1 calc R . .
H5B H 0.2532 0.0048 0.3268 0.046 Uiso 1 1 calc R . .
C6 C 0.3099(6) 0.2140(12) 0.4125(4) 0.0574(19) Uani 1 1 d . . .
H6A H 0.2905 0.1143 0.4538 0.069 Uiso 1 1 calc R . .
H6B H 0.3845 0.2390 0.4212 0.069 Uiso 1 1 calc R . .
C7 C 0.1953(4) 0.2083(9) 0.1877(3) 0.0316(12) Uani 1 1 d . . .
H7A H 0.1425 0.2962 0.1616 0.038 Uiso 1 1 calc R . .
H7B H 0.1651 0.0754 0.1902 0.038 Uiso 1 1 calc R . .
C8 C 0.2863(4) 0.2017(8) 0.1325(3) 0.0289(12) Uani 1 1 d . . .
C9 C 0.3506(4) 0.0417(8) 0.1282(3) 0.0316(12) Uani 1 1 d . . .
C10 C 0.4342(4) 0.0384(9) 0.0784(3) 0.0294(11) Uani 1 1 d . . .
C11 C 0.4552(4) 0.1949(8) 0.0268(3) 0.0288(11) Uani 1 1 d . . .
C12 C 0.3888(4) 0.3530(7) 0.0272(3) 0.0291(12) Uani 1 1 d . . .
C13 C 0.3060(4) 0.3549(8) 0.0805(3) 0.0310(12) Uani 1 1 d . . .


_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(6) . ?
F10 C10 1.326(6) . ?
F12 C12 1.339(6) . ?
F13 C13 1.345(6) . ?
N1 C4 1.508(7) . ?
N1 C5 1.509(7) . ?
N1 C7 1.509(6) . ?
N1 C1 1.515(5) . ?
N2 C6 1.452(9) . ?
N2 C2 1.458(10) . ?
N2 C3 1.461(9) . ?
C1 C2 1.542(8) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.530(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.531(9) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.515(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.368(7) . ?
C8 C9 1.380(8) . ?
C9 C10 1.382(7) . ?
C10 C11 1.385(8) . ?
C11 C12 1.384(7) . ?
C11 C11 1.482(10) 2_655 ?
C12 C13 1.408(7) . ?

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 C5 108.9(4) . . ?
C4 N1 C7 111.6(4) . . ?
C5 N1 C7 111.6(5) . . ?
C4 N1 C1 109.8(5) . . ?
C5 N1 C1 108.2(5) . . ?
C7 N1 C1 106.8(4) . . ?
C6 N2 C2 107.7(6) . . ?
C6 N2 C3 108.9(5) . . ?
C2 N2 C3 107.9(6) . . ?
N1 C1 C2 107.7(4) . . ?
N1 C1 H1A 110.2 . . ?
C2 C1 H1A 110.2 . . ?
N1 C1 H1B 110.2 . . ?
C2 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
N2 C2 C1 112.5(5) . . ?
N2 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
N2 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
N2 C3 C4 113.1(5) . . ?
N2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
N2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
N1 C4 C3 107.5(4) . . ?
N1 C4 H4A 110.2 . . ?
C3 C4 H4A 110.2 . . ?
N1 C4 H4B 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
N1 C5 C6 108.2(5) . . ?
N1 C5 H5A 110.1 . . ?
C6 C5 H5A 110.1 . . ?
N1 C5 H5B 110.1 . . ?
C6 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
N2 C6 C5 112.6(6) . . ?
N2 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
N2 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
N1 C7 C8 114.2(4) . . ?
N1 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C13 C8 C9 116.3(4) . . ?
C13 C8 C7 120.5(5) . . ?
C9 C8 C7 123.2(5) . . ?
F9 C9 C8 120.0(4) . . ?
F9 C9 C10 117.3(5) . . ?
C8 C9 C10 122.7(5) . . ?
F10 C10 C9 118.5(5) . . ?
F10 C10 C11 120.4(4) . . ?
C9 C10 C11 121.0(5) . . ?
C12 C11 C10 117.1(4) . . ?
C12 C11 C11 120.9(4) . 2_655 ?
C10 C11 C11 121.9(4) . 2_655 ?
F12 C12 C11 121.5(4) . . ?
F12 C12 C13 117.9(4) . . ?
C11 C12 C13 120.6(4) . . ?
F13 C13 C8 121.2(4) . . ?
F13 C13 C12 116.6(4) . . ?
C8 C13 C12 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
C4 N1 C1 C2 -61.9(7) . . . . ?
C5 N1 C1 C2 56.8(8) . . . . ?
C7 N1 C1 C2 177.0(6) . . . . ?
C6 N2 C2 C1 -62.1(8) . . . . ?
C3 N2 C2 C1 55.4(9) . . . . ?
N1 C1 C2 N2 4.9(10) . . . . ?
C6 N2 C3 C4 53.9(8) . . . . ?
C2 N2 C3 C4 -62.8(8) . . . . ?
C5 N1 C4 C3 -62.8(6) . . . . ?
C7 N1 C4 C3 173.6(5) . . . . ?
C1 N1 C4 C3 55.4(6) . . . . ?
N2 C3 C4 N1 6.7(8) . . . . ?
C4 N1 C5 C6 56.8(6) . . . . ?
C7 N1 C5 C6 -179.6(5) . . . . ?
C1 N1 C5 C6 -62.4(6) . . . . ?
C2 N2 C6 C5 56.4(7) . . . . ?
C3 N2 C6 C5 -60.4(7) . . . . ?
N1 C5 C6 N2 4.8(7) . . . . ?
C4 N1 C7 C8 54.6(6) . . . . ?
C5 N1 C7 C8 -67.4(6) . . . . ?
C1 N1 C7 C8 174.6(5) . . . . ?
N1 C7 C8 C13 -95.8(6) . . . . ?
N1 C7 C8 C9 87.3(7) . . . . ?
C13 C8 C9 F9 -178.4(5) . . . . ?
C7 C8 C9 F9 -1.4(8) . . . . ?
C13 C8 C9 C10 3.9(8) . . . . ?
C7 C8 C9 C10 -179.1(5) . . . . ?
F9 C9 C10 F10 -2.3(7) . . . . ?
C8 C9 C10 F10 175.5(5) . . . . ?
F9 C9 C10 C11 179.3(5) . . . . ?
C8 C9 C10 C11 -3.0(8) . . . . ?
F10 C10 C11 C12 -178.6(5) . . . . ?
C9 C10 C11 C12 -0.2(7) . . . . ?
F10 C10 C11 C11 1.3(9) . . . 2_655 ?
C9 C10 C11 C11 179.7(6) . . . 2_655 ?
C10 C11 C12 F12 -177.1(5) . . . . ?
C11 C11 C12 F12 3.0(9) 2_655 . . . ?
C10 C11 C12 C13 2.2(7) . . . . ?
C11 C11 C12 C13 -177.8(6) 2_655 . . . ?
C9 C8 C13 F13 177.7(5) . . . . ?
C7 C8 C13 F13 0.7(8) . . . . ?
C9 C8 C13 C12 -1.9(8) . . . . ?
C7 C8 C13 C12 -178.9(5) . . . . ?
F12 C12 C13 F13 -1.5(7) . . . . ?
C11 C12 C13 F13 179.2(5) . . . . ?
F12 C12 C13 C8 178.2(5) . . . . ?
C11 C12 C13 C8 -1.1(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.070

_database_code_depnum_ccdc_archive 'CCDC 1014200'
#######################################################################
#
#                 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_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 F7 N2, C H4 O, Br'
_chemical_formula_sum            'C18 H18 Br F7 N2 O'
_chemical_formula_weight         491.25

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           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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-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                   13.6470(3)
_cell_length_b                   12.4533(2)
_cell_length_c                   22.0643(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3749.83(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5133
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1968
_exptl_absorpt_coefficient_mu    2.272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5896
_exptl_absorpt_correction_T_max  0.8571
_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            21666
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         25.25
_reflns_number_total             3389
_reflns_number_gt                2345
_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)+(0.0423P)²+11.1433P] 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         3389
_refine_ls_number_parameters     266
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.036
_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 0.49884(3) 0.65545(3) 0.26118(2) 0.02803(16) Uani 1 1 d . . .
F9 F 0.2598(2) 0.6697(2) 0.38207(12) 0.0385(7) Uani 1 1 d . . .
F10 F 0.4122(2) 0.7821(2) 0.42149(13) 0.0453(8) Uani 1 1 d . . .
F12 F 0.5905(2) 0.7829(3) 0.45865(15) 0.0569(9) Uani 1 1 d . . .
F13 F 0.7541(2) 0.6773(3) 0.49057(16) 0.0712(11) Uani 1 1 d . . .
F14 F 0.7625(3) 0.4568(4) 0.47909(16) 0.0715(11) Uani 1 1 d . . .
F15 F 0.6079(2) 0.3475(3) 0.43636(13) 0.0465(8) Uani 1 1 d . . .
F17 F 0.4370(2) 0.3454(2) 0.39151(13) 0.0438(7) Uani 1 1 d . . .
N1 N 0.2573(3) 0.4401(3) 0.29067(17) 0.0261(8) Uani 1 1 d . . .
N2 N 0.2395(3) 0.4256(3) 0.17475(17) 0.0285(9) Uani 1 1 d . . .
C1 C 0.3468(3) 0.3861(4) 0.2636(2) 0.0288(10) Uani 1 1 d . . .
H1A H 0.3591 0.3166 0.2840 0.035 Uiso 1 1 calc R . .
H1B H 0.4053 0.4322 0.2690 0.035 Uiso 1 1 calc R . .
C2 C 0.3270(4) 0.3678(4) 0.1954(2) 0.0346(12) Uani 1 1 d . . .
H2A H 0.3844 0.3924 0.1717 0.041 Uiso 1 1 calc R . .
H2B H 0.3183 0.2901 0.1878 0.041 Uiso 1 1 calc R . .
C3 C 0.2496(3) 0.5390(4) 0.1934(2) 0.0273(10) Uani 1 1 d . . .
H3A H 0.1953 0.5815 0.1758 0.033 Uiso 1 1 calc R . .
H3B H 0.3121 0.5681 0.1775 0.033 Uiso 1 1 calc R . .
C4 C 0.2480(3) 0.5502(3) 0.26304(19) 0.0243(9) Uani 1 1 d . . .
H4A H 0.3029 0.5962 0.2766 0.029 Uiso 1 1 calc R . .
H4B H 0.1858 0.5840 0.2761 0.029 Uiso 1 1 calc R . .
C5 C 0.1681(3) 0.3739(4) 0.2737(2) 0.0323(11) Uani 1 1 d . . .
H5A H 0.1094 0.4019 0.2947 0.039 Uiso 1 1 calc R . .
H5B H 0.1778 0.2982 0.2860 0.039 Uiso 1 1 calc R . .
C6 C 0.1540(4) 0.3809(4) 0.2049(2) 0.0375(12) Uani 1 1 d . . .
H6A H 0.1409 0.3082 0.1886 0.045 Uiso 1 1 calc R . .
H6B H 0.0962 0.4263 0.1959 0.045 Uiso 1 1 calc R . .
C7 C 0.2615(3) 0.4456(4) 0.3589(2) 0.0287(10) Uani 1 1 d . . .
H7A H 0.2012 0.4809 0.3739 0.034 Uiso 1 1 calc R . .
H7B H 0.2623 0.3715 0.3752 0.034 Uiso 1 1 calc R . .
C8 C 0.3488(3) 0.5050(4) 0.3834(2) 0.0302(11) Uani 1 1 d . . .
C9 C 0.3437(3) 0.6186(4) 0.3936(2) 0.0314(11) Uani 1 1 d . . .
C10 C 0.4210(4) 0.6751(4) 0.4153(2) 0.0369(12) Uani 1 1 d . . .
C11 C 0.5098(4) 0.6223(4) 0.4294(2) 0.0361(12) Uani 1 1 d . . .
C12 C 0.5938(4) 0.6765(5) 0.4522(2) 0.0472(15) Uani 1 1 d . . .
C13 C 0.6770(4) 0.6215(5) 0.4673(2) 0.0428(14) Uani 1 1 d . . .
C14 C 0.6811(4) 0.5107(5) 0.4622(2) 0.0440(14) Uani 1 1 d . . .
C15 C 0.6040(4) 0.4557(5) 0.4403(2) 0.0441(14) Uani 1 1 d . . .
C16 C 0.5167(4) 0.5090(4) 0.4230(2) 0.0350(12) Uani 1 1 d . . .
C17 C 0.4335(4) 0.4554(4) 0.3989(2) 0.0345(12) Uani 1 1 d . . .
O18 O 0.5338(3) 0.5296(4) 0.13511(19) 0.0611(12) Uani 1 1 d D . .
H18 H 0.526(5) 0.568(5) 0.166(2) 0.092 Uiso 1 1 d D . .
C18 C 0.4963(5) 0.5739(6) 0.0821(3) 0.075(2) Uani 1 1 d . . .
H18A H 0.5461 0.6196 0.0632 0.113 Uiso 1 1 calc R . .
H18B H 0.4383 0.6171 0.0917 0.113 Uiso 1 1 calc R . .
H18C H 0.4781 0.5162 0.0541 0.113 Uiso 1 1 calc R . .


_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(5) . ?
F10 C10 1.345(6) . ?
F12 C12 1.334(6) . ?
F13 C13 1.361(6) . ?
F14 C14 1.350(6) . ?
F15 C15 1.351(6) . ?
F17 C17 1.381(6) . ?
N1 C4 1.506(5) . ?
N1 C7 1.509(6) . ?
N1 C1 1.517(5) . ?
N1 C5 1.517(6) . ?
N2 C6 1.453(6) . ?
N2 C2 1.467(6) . ?
N2 C3 1.477(6) . ?
C1 C2 1.545(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.543(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.533(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.503(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C17 1.355(7) . ?
C8 C9 1.433(7) . ?
C9 C10 1.355(7) . ?
C10 C11 1.413(7) . ?
C11 C16 1.422(7) . ?
C11 C12 1.422(7) . ?
C12 C13 1.368(8) . ?
C13 C14 1.385(8) . ?
C14 C15 1.346(8) . ?
C15 C16 1.417(7) . ?
C16 C17 1.419(7) . ?
O18 C18 1.390(7) . ?
O18 H18 0.84(2) . ?
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
C4 N1 C7 111.5(3) . . ?
C4 N1 C1 108.2(3) . . ?
C7 N1 C1 112.5(3) . . ?
C4 N1 C5 109.1(3) . . ?
C7 N1 C5 107.5(3) . . ?
C1 N1 C5 107.9(4) . . ?
C6 N2 C2 108.9(4) . . ?
C6 N2 C3 108.3(4) . . ?
C2 N2 C3 107.8(4) . . ?
N1 C1 C2 107.9(4) . . ?
N1 C1 H1A 110.1 . . ?
C2 C1 H1A 110.1 . . ?
N1 C1 H1B 110.1 . . ?
C2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
N2 C2 C1 111.9(4) . . ?
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 . . ?
N2 C3 C4 111.2(3) . . ?
N2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
N1 C4 C3 108.7(3) . . ?
N1 C4 H4A 110.0 . . ?
C3 C4 H4A 110.0 . . ?
N1 C4 H4B 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 C6 108.4(4) . . ?
N1 C5 H5A 110.0 . . ?
C6 C5 H5A 110.0 . . ?
N1 C5 H5B 110.0 . . ?
C6 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
N2 C6 C5 111.9(4) . . ?
N2 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 N1 114.2(4) . . ?
C8 C7 H7A 108.7 . . ?
N1 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
N1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C17 C8 C9 116.8(5) . . ?
C17 C8 C7 122.9(4) . . ?
C9 C8 C7 120.3(4) . . ?
F9 C9 C10 119.2(4) . . ?
F9 C9 C8 118.8(4) . . ?
C10 C9 C8 122.0(5) . . ?
F10 C10 C9 118.8(5) . . ?
F10 C10 C11 120.9(5) . . ?
C9 C10 C11 120.3(5) . . ?
C10 C11 C16 119.7(5) . . ?
C10 C11 C12 123.3(5) . . ?
C16 C11 C12 116.9(5) . . ?
F12 C12 C13 120.0(5) . . ?
F12 C12 C11 118.8(5) . . ?
C13 C12 C11 121.2(5) . . ?
F13 C13 C12 118.5(6) . . ?
F13 C13 C14 120.5(5) . . ?
C12 C13 C14 120.9(5) . . ?
C15 C14 F14 119.3(6) . . ?
C15 C14 C13 120.3(5) . . ?
F14 C14 C13 120.4(5) . . ?
C14 C15 F15 120.0(5) . . ?
C14 C15 C16 121.0(6) . . ?
F15 C15 C16 118.9(5) . . ?
C15 C16 C17 123.6(5) . . ?
C15 C16 C11 119.6(5) . . ?
C17 C16 C11 116.8(4) . . ?
C8 C17 F17 116.9(4) . . ?
C8 C17 C16 124.2(5) . . ?
F17 C17 C16 118.9(4) . . ?
C18 O18 H18 115(5) . . ?
O18 C18 H18A 109.5 . . ?
O18 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O18 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
C4 N1 C1 C2 -65.8(4) . . . . ?
C7 N1 C1 C2 170.6(4) . . . . ?
C5 N1 C1 C2 52.1(5) . . . . ?
C6 N2 C2 C1 -65.2(5) . . . . ?
C3 N2 C2 C1 52.2(5) . . . . ?
N1 C1 C2 N2 11.4(5) . . . . ?
C6 N2 C3 C4 51.9(5) . . . . ?
C2 N2 C3 C4 -65.8(5) . . . . ?
C7 N1 C4 C3 177.1(3) . . . . ?
C1 N1 C4 C3 52.9(4) . . . . ?
C5 N1 C4 C3 -64.3(4) . . . . ?
N2 C3 C4 N1 11.5(5) . . . . ?
C4 N1 C5 C6 50.9(5) . . . . ?
C7 N1 C5 C6 171.9(4) . . . . ?
C1 N1 C5 C6 -66.5(5) . . . . ?
C2 N2 C6 C5 50.5(5) . . . . ?
C3 N2 C6 C5 -66.5(5) . . . . ?
N1 C5 C6 N2 13.3(6) . . . . ?
C4 N1 C7 C8 -62.9(5) . . . . ?
C1 N1 C7 C8 58.9(5) . . . . ?
C5 N1 C7 C8 177.6(4) . . . . ?
N1 C7 C8 C17 -93.1(5) . . . . ?
N1 C7 C8 C9 89.5(5) . . . . ?
C17 C8 C9 F9 -176.4(4) . . . . ?
C7 C8 C9 F9 1.2(6) . . . . ?
C17 C8 C9 C10 2.8(7) . . . . ?
C7 C8 C9 C10 -179.6(4) . . . . ?
F9 C9 C10 F10 -3.4(7) . . . . ?
C8 C9 C10 F10 177.4(4) . . . . ?
F9 C9 C10 C11 178.3(4) . . . . ?
C8 C9 C10 C11 -0.9(7) . . . . ?
F10 C10 C11 C16 179.4(4) . . . . ?
C9 C10 C11 C16 -2.4(7) . . . . ?
F10 C10 C11 C12 1.6(7) . . . . ?
C9 C10 C11 C12 179.8(5) . . . . ?
C10 C11 C12 F12 -2.4(7) . . . . ?
C16 C11 C12 F12 179.7(4) . . . . ?
C10 C11 C12 C13 177.6(5) . . . . ?
C16 C11 C12 C13 -0.3(7) . . . . ?
F12 C12 C13 F13 1.9(7) . . . . ?
C11 C12 C13 F13 -178.1(4) . . . . ?
F12 C12 C13 C14 178.6(5) . . . . ?
C11 C12 C13 C14 -1.4(8) . . . . ?
F13 C13 C14 C15 178.8(5) . . . . ?
C12 C13 C14 C15 2.2(8) . . . . ?
F13 C13 C14 F14 -1.3(8) . . . . ?
C12 C13 C14 F14 -177.9(5) . . . . ?
F14 C14 C15 F15 1.2(7) . . . . ?
C13 C14 C15 F15 -178.9(4) . . . . ?
F14 C14 C15 C16 178.9(4) . . . . ?
C13 C14 C15 C16 -1.2(8) . . . . ?
C14 C15 C16 C17 179.2(5) . . . . ?
F15 C15 C16 C17 -3.1(7) . . . . ?
C14 C15 C16 C11 -0.5(7) . . . . ?
F15 C15 C16 C11 177.2(4) . . . . ?
C10 C11 C16 C15 -176.7(4) . . . . ?
C12 C11 C16 C15 1.2(7) . . . . ?
C10 C11 C16 C17 3.6(7) . . . . ?
C12 C11 C16 C17 -178.5(4) . . . . ?
C9 C8 C17 F17 177.3(4) . . . . ?
C7 C8 C17 F17 -0.2(7) . . . . ?
C9 C8 C17 C16 -1.5(7) . . . . ?
C7 C8 C17 C16 -179.0(4) . . . . ?
C15 C16 C17 C8 178.6(5) . . . . ?
C11 C16 C17 C8 -1.6(7) . . . . ?
C15 C16 C17 F17 -0.2(7) . . . . ?
C11 C16 C17 F17 179.6(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
O18 H18 Br1 0.84(2) 2.39(2) 3.228(4) 173(7) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.720
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.093

_database_code_depnum_ccdc_archive 'CCDC 1014201'
