# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3613
_database_code_depnum_ccdc_archive 'CCDC 1496147'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;
_audit_creation_date             2014-08-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H12 Br2'
_chemical_formula_sum            'C18 H12 Br2'
_chemical_formula_weight         388.10
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.3248(4)
_cell_length_b                   17.2473(10)
_cell_length_c                   7.6729(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.167(6)
_cell_angle_gamma                90.00
_cell_volume                     700.59(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3627
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      29.36
_cell_measurement_temperature    123
_exptl_absorpt_coefficient_mu    5.771
_exptl_absorpt_correction_T_max  0.4121
_exptl_absorpt_correction_T_min  0.2745
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'STOE XRed 1.35'
_exptl_crystal_colour            'clear orangish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5835
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.98
_diffrn_reflns_theta_min         2.92
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS-2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.00
_diffrn_source_voltage           50
_diffrn_special_details          ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1119
_reflns_number_total             1673
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.840
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1673
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0231
_refine_ls_restrained_S_all      0.840
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0289P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0494
_refine_ls_wR_factor_ref         0.0525
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C6(H6)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br Br 0.02685(4) 0.248290(19) 0.94122(3) 0.02607(8) Uani 1 d . . .
C4 C 0.4842(5) 0.44300(14) 0.6977(4) 0.0196(5) Uani 1 d . . .
C8 C 0.7666(4) 0.55494(13) 0.5776(3) 0.0194(5) Uani 1 d . . .
C1 C 0.2113(5) 0.32851(14) 0.8414(3) 0.0211(5) Uani 1 d . . .
C3 C 0.5578(5) 0.41844(15) 0.8671(4) 0.0223(5) Uani 1 d . . .
H3 H 0.7004 0.4409 0.9334 0.027 Uiso 1 calc . . R
C9 C 0.9686(5) 0.57957(15) 0.7156(4) 0.0221(5) Uani 1 d . . .
H9A H 0.9604 0.5478 0.8207 0.033 Uiso 1 calc . . GR
H9B H 0.9444 0.6342 0.7445 0.033 Uiso 1 calc . . GR
H9C H 1.1339 0.5729 0.6724 0.033 Uiso 1 calc . . GR
C2 C 0.4188(5) 0.35992(14) 0.9393(4) 0.0232(5) Uani 1 d . . .
H2 H 0.4672 0.3420 1.0550 0.028 Uiso 1 calc . . R
C6 C 0.1306(5) 0.35192(13) 0.6707(3) 0.0202(5) Uani 1 d . . .
H6 H -0.0134 0.3295 0.6061 0.024 Uiso 1 calc . . R
C7 C 0.5820(5) 0.50098(13) 0.5829(3) 0.0192(5) Uani 1 d . . .
C5 C 0.2704(4) 0.40950(13) 0.5996(3) 0.0184(5) Uani 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
Br C1 1.904(2) . ?
C4 C3 1.383(4) . ?
C4 C7 1.465(3) . ?
C4 C5 1.418(4) . ?
C8 C9 1.488(4) . ?
C8 C7 1.357(3) . ?
C8 C5 1.485(3) 3_666 ?
C1 C2 1.378(4) . ?
C1 C6 1.393(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.401(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C2 H2 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.388(3) . ?
C7 C7 1.464(5) 3_666 ?
C5 C8 1.485(3) 3_666 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C4 C7 133.7(2) . . ?
C3 C4 C5 120.3(2) . . ?
C5 C4 C7 106.0(2) . . ?
C7 C8 C9 130.2(2) . . ?
C7 C8 C5 106.6(2) . 3_666 ?
C5 C8 C9 123.2(2) 3_666 . ?
C2 C1 Br 118.97(19) . . ?
C2 C1 C6 123.1(2) . . ?
C6 C1 Br 117.92(19) . . ?
C4 C3 H3 120.5 . . ?
C4 C3 C2 118.9(3) . . ?
C2 C3 H3 120.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C1 C6 H6 121.5 . . ?
C5 C6 C1 116.9(2) . . ?
C5 C6 H6 121.5 . . ?
C8 C7 C4 142.3(2) . . ?
C8 C7 C7 110.9(3) . 3_666 ?
C7 C7 C4 106.8(3) 3_666 . ?
C4 C5 C8 109.7(2) . 3_666 ?
C6 C5 C4 121.1(2) . . ?
C6 C5 C8 129.2(2) . 3_666 ?

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
Br C1 C2 C3 179.38(19) . . . . ?
Br C1 C6 C5 -178.90(17) . . . . ?
C4 C3 C2 C1 -0.5(4) . . . . ?
C1 C6 C5 C4 -0.5(3) . . . . ?
C1 C6 C5 C8 179.0(2) . . . 3_666 ?
C3 C4 C7 C8 -0.8(5) . . . . ?
C3 C4 C7 C7 179.9(3) . . . 3_666 ?
C3 C4 C5 C8 -179.4(2) . . . 3_666 ?
C3 C4 C5 C6 0.2(4) . . . . ?
C9 C8 C7 C4 -2.0(5) . . . . ?
C9 C8 C7 C7 177.4(2) . . . 3_666 ?
C2 C1 C6 C5 0.2(3) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
C7 C4 C3 C2 -179.8(2) . . . . ?
C7 C4 C5 C8 0.7(3) . . . 3_666 ?
C7 C4 C5 C6 -179.7(2) . . . . ?
C5 C4 C3 C2 0.3(4) . . . . ?
C5 C4 C7 C8 179.2(3) . . . . ?
C5 C4 C7 C7 -0.2(3) . . . 3_666 ?
C5 C8 C7 C4 179.8(3) 3_666 . . . ?
C5 C8 C7 C7 -0.8(3) 3_666 . . 3_666 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3666f
_database_code_depnum_ccdc_archive 'CCDC 1496148'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;
_audit_creation_date             2014-09-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H16 Br2'
_chemical_formula_sum            'C20 H16 Br2'
_chemical_formula_weight         416.15
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.6723(15)
_cell_length_b                   8.653(2)
_cell_length_c                   15.099(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.660(10)
_cell_angle_gamma                90
_cell_volume                     810.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7496
_cell_measurement_temperature    123
_cell_measurement_theta_max      30.92
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   0.585
_shelx_estimated_absorpt_T_min   0.335
_exptl_absorpt_coefficient_mu    4.996
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.3613
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1301 before and 0.0836 after correction.
The Ratio of minimum to maximum transmission is 0.4842.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14546
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         2.766
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker X8-KappaApexII'
_diffrn_measurement_method       'fine slicing ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1484
_reflns_number_total             1952
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.163
_refine_diff_density_min         -2.027
_refine_diff_density_rms         0.198
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1952
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0628
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1066P)²+2.4968P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.1831
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.04212(9) -0.90594(7) -0.21256(4) 0.0357(3) Uani 1 1 d . . . . .
C1 C 0.2072(9) -0.9007(6) -0.2931(4) 0.0273(11) Uani 1 1 d . . . . .
C2 C 0.3440(8) -0.7773(6) -0.2855(4) 0.0264(10) Uani 1 1 d . . . . .
H2 H 0.3546 -0.6960 -0.2417 0.032 Uiso 1 1 calc R . . . .
C3 C 0.4672(8) -0.7736(6) -0.3434(4) 0.0256(10) Uani 1 1 d . . . . .
H3 H 0.5632 -0.6904 -0.3391 0.031 Uiso 1 1 calc R . . . .
C4 C 0.4461(8) -0.8939(6) -0.4070(3) 0.0227(10) Uani 1 1 d . . . . .
C5 C 0.2995(8) -1.0171(6) -0.4144(3) 0.0233(10) Uani 1 1 d . . . . .
C6 C 0.1770(8) -1.0225(6) -0.3579(4) 0.0255(10) Uani 1 1 d . . . . .
H6 H 0.0780 -1.1039 -0.3628 0.031 Uiso 1 1 calc R . . . .
C7 C 0.5455(8) -0.9267(5) -0.4773(4) 0.0240(10) Uani 1 1 d . . . . .
C8 C 0.6940(8) -0.8715(6) -0.5114(4) 0.0250(10) Uani 1 1 d . . . . .
C9 C 0.8220(8) -0.7246(6) -0.4868(4) 0.0258(10) Uani 1 1 d . . . . .
H9A H 0.9671 -0.7432 -0.4883 0.031 Uiso 1 1 calc R . . . .
H9B H 0.8403 -0.6931 -0.4212 0.031 Uiso 1 1 calc R . . . .
C10 C 0.7133(9) -0.5939(6) -0.5555(4) 0.0272(11) Uani 1 1 d . . . . .
H10A H 0.7979 -0.4989 -0.5350 0.041 Uiso 1 1 calc GR . . . .
H10B H 0.5678 -0.5774 -0.5558 0.041 Uiso 1 1 calc GR . . . .
H10C H 0.7045 -0.6214 -0.6198 0.041 Uiso 1 1 calc GR . . . .


_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
Br C1 1.919(5) . ?
C1 C2 1.382(8) . ?
C1 C6 1.401(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.405(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(7) . ?
C4 C5 1.423(7) . ?
C4 C7 1.472(7) . ?
C5 C6 1.383(7) . ?
C5 C8 1.491(7) 3_634 ?
C6 H6 0.9500 . ?
C7 C7 1.462(10) 3_634 ?
C7 C8 1.360(7) . ?
C8 C5 1.491(7) 3_634 ?
C8 C9 1.500(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.524(7) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br 118.8(4) . . ?
C2 C1 C6 124.0(5) . . ?
C6 C1 Br 117.2(4) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.1(5) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.7(5) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 120.5(5) . . ?
C3 C4 C7 133.3(5) . . ?
C5 C4 C7 106.2(4) . . ?
C4 C5 C8 109.5(4) . 3_634 ?
C6 C5 C4 121.5(5) . . ?
C6 C5 C8 129.0(5) . 3_634 ?
C1 C6 H6 121.9 . . ?
C5 C6 C1 116.1(5) . . ?
C5 C6 H6 121.9 . . ?
C7 C7 C4 106.6(5) 3_634 . ?
C8 C7 C4 142.1(5) . . ?
C8 C7 C7 111.2(6) . 3_634 ?
C5 C8 C9 124.2(4) 3_634 . ?
C7 C8 C5 106.5(4) . 3_634 ?
C7 C8 C9 129.2(5) . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C8 C9 C10 112.1(4) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
Br C1 C2 C3 179.2(4) . . . . ?
Br C1 C6 C5 -179.3(4) . . . . ?
C1 C2 C3 C4 0.5(7) . . . . ?
C2 C1 C6 C5 2.1(8) . . . . ?
C2 C3 C4 C5 1.0(7) . . . . ?
C2 C3 C4 C7 179.4(5) . . . . ?
C3 C4 C5 C6 -1.0(8) . . . . ?
C3 C4 C5 C8 179.0(5) . . . 3_634 ?
C3 C4 C7 C7 -179.8(6) . . . 3_634 ?
C3 C4 C7 C8 3.1(12) . . . . ?
C4 C5 C6 C1 -0.5(7) . . . . ?
C4 C7 C8 C5 178.7(7) . . . 3_634 ?
C4 C7 C8 C9 -4.6(11) . . . . ?
C5 C4 C7 C7 -1.2(7) . . . 3_634 ?
C5 C4 C7 C8 -178.4(7) . . . . ?
C5 C8 C9 C10 82.2(6) 3_634 . . . ?
C6 C1 C2 C3 -2.2(8) . . . . ?
C7 C4 C5 C6 -179.8(5) . . . . ?
C7 C4 C5 C8 0.3(6) . . . 3_634 ?
C7 C7 C8 C5 1.7(7) 3_634 . . 3_634 ?
C7 C7 C8 C9 178.4(5) 3_634 . . . ?
C7 C8 C9 C10 -94.0(7) . . . . ?
C8 C5 C6 C1 179.4(5) 3_634 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3698
_database_code_depnum_ccdc_archive 'CCDC 1496149'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;
_audit_creation_date             2014-10-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.5(C56 H32 Br4)'
_chemical_formula_sum            'C28 H16 Br2'
_chemical_formula_weight         512.23
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.802(3)
_cell_length_b                   4.9336(5)
_cell_length_c                   18.875(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.188(13)
_cell_angle_gamma                90.00
_cell_volume                     2030.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1335
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      23.83
_cell_measurement_temperature    123
_exptl_absorpt_coefficient_mu    4.006
_exptl_absorpt_correction_T_max  0.9154
_exptl_absorpt_correction_T_min  0.7334
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1924
_diffrn_reflns_av_unetI/netI     0.2136
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9384
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.85
_diffrn_ambient_temperature      123
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS-2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.00
_diffrn_source_voltage           50
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1112
_reflns_number_total             2450
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.899
_refine_diff_density_min         -1.620
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.831
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2450
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.0681
_refine_ls_restrained_S_all      0.831
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0760P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1570
_refine_ls_wR_factor_ref         0.1785
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Br \\sim Br1S \\sim C6: within 1.7A with sigma of 0.009 and sigma for terminal
atoms of 0.018
Uanis(C12) \\sim Ueq, Uanis(C12S) \\sim Ueq, Uanis(C13S) \\sim Ueq: with sigma
of 0.009 and sigma for terminal atoms of 0.018
Uanis(Br1S) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.016
3. Others
 Sof(C14)=Sof(H14)=Sof(C10)=Sof(H10)=Sof(C13)=Sof(H13)=Sof(C11)=Sof(H11)=
 Sof(C12)=Sof(H12)=1-FVAR(1)
 Sof(C14S)=Sof(H14S)=Sof(C10S)=Sof(H10S)=Sof(C11S)=Sof(H11S)=Sof(C13S)=
 Sof(H13S)=Sof(C12S)=Sof(H12S)=FVAR(1)
 Sof(Br1S)=1-FVAR(2)
 Sof(Br)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C7(H7), C14S(H14S), C10S(H10S), C11S(H11S), C13S(H13S),
 C12S(H12S), C14(H14), C10(H10), C13(H13), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C9 C 0.1227(4) -0.9206(16) 0.0613(4) 0.0313(19) Uani 1 d . . . .
C1 C 0.1774(4) -0.8999(16) 0.0183(4) 0.0322(17) Uani 1 d . . . .
C6 C 0.3250(4) -0.1466(15) 0.1452(5) 0.037(2) Uani 1 d . . . .
C3 C 0.2528(4) -0.5271(15) 0.0779(4) 0.0265(17) Uani 1 d A . . .
C5 C 0.2686(4) -0.2248(15) 0.1747(4) 0.0319(19) Uani 1 d A . . .
H5 H 0.2546 -0.1439 0.2173 0.038 Uiso 1 calc . . R .
C2 C 0.2282(4) -0.7337(14) 0.0284(4) 0.0303(19) Uani 1 d . . . .
C4 C 0.2333(4) -0.4231(16) 0.1406(4) 0.0344(19) Uani 1 d . . . .
H4 H 0.1960 -0.4843 0.1611 0.041 Uiso 1 calc A . R .
C8 C 0.3104(4) -0.4509(15) 0.0476(4) 0.0279(19) Uani 1 d . . . .
C7 C 0.3454(4) -0.2557(15) 0.0820(4) 0.034(2) Uani 1 d A . . .
H7 H 0.3831 -0.1973 0.0622 0.041 Uiso 1 calc . . R .
C14S C 0.0988(8) -1.175(3) 0.0827(9) 0.031(5) Uani 0.469(11) d A 1 . .
H14S H 0.1181 -1.3378 0.0680 0.037 Uiso 0.469(11) calc A 1 R .
C10S C 0.0934(9) -0.694(4) 0.0856(9) 0.034(5) Uani 0.469(11) d A 1 . .
H10S H 0.1081 -0.5200 0.0723 0.041 Uiso 0.469(11) calc A 1 R .
C11S C 0.0434(9) -0.713(4) 0.1286(11) 0.044(5) Uani 0.469(11) d A 1 . .
H11S H 0.0235 -0.5510 0.1427 0.053 Uiso 0.469(11) calc A 1 R .
C13S C 0.0465(9) -1.185(3) 0.1254(9) 0.034(4) Uani 0.469(11) d A 1 . U
H13S H 0.0290 -1.3570 0.1356 0.040 Uiso 0.469(11) calc A 1 R .
C12S C 0.0198(19) -0.960(8) 0.1529(17) 0.038(9) Uani 0.469(11) d A 1 . U
H12S H -0.0126 -0.9697 0.1863 0.045 Uiso 0.469(11) calc A 1 R .
C14 C 0.1235(7) -0.913(3) 0.1331(8) 0.035(4) Uani 0.531(11) d A 2 . .
H14 H 0.1612 -0.8927 0.1579 0.042 Uiso 0.531(11) calc A 2 R .
C10 C 0.0644(8) -0.941(3) 0.0270(9) 0.042(5) Uani 0.531(11) d A 2 . .
H10 H 0.0629 -0.9441 -0.0233 0.050 Uiso 0.531(11) calc A 2 R .
C13 C 0.0685(9) -0.935(3) 0.1700(9) 0.045(5) Uani 0.531(11) d A 2 . .
H13 H 0.0691 -0.9394 0.2204 0.054 Uiso 0.531(11) calc A 2 R .
C11 C 0.0098(8) -0.957(3) 0.0645(11) 0.048(5) Uani 0.531(11) d A 2 . .
H11 H -0.0286 -0.9702 0.0408 0.057 Uiso 0.531(11) calc A 2 R .
C12 C 0.0130(14) -0.952(5) 0.1341(14) 0.026(6) Uani 0.531(11) d A 2 . U
H12 H -0.0239 -0.9596 0.1607 0.032 Uiso 0.531(11) calc A 2 R .
Br Br 0.37380(5) 0.1082(2) 0.19487(5) 0.0351(4) Uani 0.920(4) d B 1 . .
Br1S Br 0.3785(8) -0.068(4) 0.2037(9) 0.068(5) Uani 0.080(4) d B 2 . U


_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
C9 C1 1.447(11) . ?
C9 C14S 1.418(19) . ?
C9 C10S 1.368(18) . ?
C9 C14 1.354(17) . ?
C9 C10 1.43(2) . ?
C1 C2 1.391(11) . ?
C1 C8 1.471(11) 7_535 ?
C6 C5 1.404(11) . ?
C6 C7 1.384(11) . ?
C6 Br 1.893(9) . ?
C6 Br1S 1.65(2) . ?
C3 C2 1.482(11) . ?
C3 C4 1.360(11) . ?
C3 C8 1.430(11) . ?
C5 H5 0.9500 . ?
C5 C4 1.401(11) . ?
C2 C2 1.445(15) 7_535 ?
C4 H4 0.9500 . ?
C8 C1 1.471(11) 7_535 ?
C8 C7 1.389(11) . ?
C7 H7 0.9500 . ?
C14S H14S 0.9500 . ?
C14S C13S 1.40(2) . ?
C10S H10S 0.9500 . ?
C10S C11S 1.37(2) . ?
C11S H11S 0.9500 . ?
C11S C12S 1.40(4) . ?
C13S H13S 0.9500 . ?
C13S C12S 1.36(4) . ?
C12S H12S 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.39(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.39(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.39(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.32(3) . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14S C9 C1 121.8(9) . . ?
C14S C9 C10 74.8(11) . . ?
C10S C9 C1 121.1(10) . . ?
C10S C9 C14S 117.1(12) . . ?
C10S C9 C10 78.1(10) . . ?
C14 C9 C1 123.4(10) . . ?
C14 C9 C14S 75.2(11) . . ?
C14 C9 C10S 69.4(10) . . ?
C14 C9 C10 117.6(11) . . ?
C10 C9 C1 118.9(9) . . ?
C9 C1 C8 126.3(7) . 7_535 ?
C2 C1 C9 128.4(7) . . ?
C2 C1 C8 105.3(7) . 7_535 ?
C5 C6 Br 118.5(6) . . ?
C5 C6 Br1S 114.7(9) . . ?
C7 C6 C5 121.2(8) . . ?
C7 C6 Br 120.2(7) . . ?
C7 C6 Br1S 116.1(9) . . ?
Br1S C6 Br 28.0(6) . . ?
C4 C3 C2 133.9(7) . . ?
C4 C3 C8 121.8(7) . . ?
C8 C3 C2 104.2(6) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 C6 119.4(8) . . ?
C4 C5 H5 120.3 . . ?
C1 C2 C3 141.1(7) . . ?
C1 C2 C2 111.0(9) . 7_535 ?
C2 C2 C3 107.8(8) 7_535 . ?
C3 C4 C5 119.3(8) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C3 C8 C1 111.7(7) . 7_535 ?
C7 C8 C1 129.9(7) . 7_535 ?
C7 C8 C3 118.5(7) . . ?
C6 C7 C8 119.7(8) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C14S H14S 120.1 . . ?
C13S C14S C9 119.8(13) . . ?
C13S C14S H14S 120.1 . . ?
C9 C10S H10S 119.5 . . ?
C11S C10S C9 121.1(16) . . ?
C11S C10S H10S 119.5 . . ?
C10S C11S H11S 118.3 . . ?
C10S C11S C12S 123(2) . . ?
C12S C11S H11S 118.3 . . ?
C14S C13S H13S 118.6 . . ?
C12S C13S C14S 123(2) . . ?
C12S C13S H13S 118.6 . . ?
C11S C12S H12S 122.3 . . ?
C13S C12S C11S 115(3) . . ?
C13S C12S H12S 122.3 . . ?
C9 C14 H14 120.3 . . ?
C9 C14 C13 119.4(15) . . ?
C13 C14 H14 120.3 . . ?
C9 C10 H10 118.8 . . ?
C11 C10 C9 122.3(15) . . ?
C11 C10 H10 118.8 . . ?
C14 C13 H13 119.6 . . ?
C12 C13 C14 120.7(17) . . ?
C12 C13 H13 119.6 . . ?
C10 C11 H11 121.1 . . ?
C12 C11 C10 118(2) . . ?
C12 C11 H11 121.1 . . ?
C13 C12 H12 118.9 . . ?
C11 C12 C13 122(2) . . ?
C11 C12 H12 118.9 . . ?

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
C9 C1 C2 C3 1.0(17) . . . . ?
C9 C1 C2 C2 -177.5(8) . . . 7_535 ?
C9 C14S C13S C12S -6(3) . . . . ?
C9 C10S C11S C12S 2(3) . . . . ?
C9 C14 C13 C12 -3(3) . . . . ?
C9 C10 C11 C12 0(3) . . . . ?
C1 C9 C14S C13S 178.7(13) . . . . ?
C1 C9 C10S C11S -177.2(15) . . . . ?
C1 C9 C14 C13 -179.8(12) . . . . ?
C1 C9 C10 C11 -178.8(12) . . . . ?
C1 C8 C7 C6 -178.4(8) 7_535 . . . ?
C6 C5 C4 C3 -3.0(12) . . . . ?
C3 C8 C7 C6 2.0(11) . . . . ?
C5 C6 C7 C8 -1.6(12) . . . . ?
C2 C3 C4 C5 179.8(8) . . . . ?
C2 C3 C8 C1 0.0(8) . . . 7_535 ?
C2 C3 C8 C7 179.7(7) . . . . ?
C4 C3 C2 C1 4.2(17) . . . . ?
C4 C3 C2 C2 -177.3(9) . . . 7_535 ?
C4 C3 C8 C1 177.2(7) . . . 7_535 ?
C4 C3 C8 C7 -3.1(11) . . . . ?
C8 C1 C2 C3 179.4(9) 7_535 . . . ?
C8 C1 C2 C2 1.0(11) 7_535 . . 7_535 ?
C8 C3 C2 C1 -179.1(10) . . . . ?
C8 C3 C2 C2 -0.6(10) . . . 7_535 ?
C8 C3 C4 C5 3.6(12) . . . . ?
C7 C6 C5 C4 2.1(12) . . . . ?
C14S C9 C1 C2 -132.4(12) . . . . ?
C14S C9 C1 C8 49.5(15) . . . 7_535 ?
C14S C9 C10S C11S 0(2) . . . . ?
C14S C9 C14 C13 -61.3(16) . . . . ?
C14S C9 C10 C11 62.9(16) . . . . ?
C14S C13S C12S C11S 8(4) . . . . ?
C10S C9 C1 C2 44.8(15) . . . . ?
C10S C9 C1 C8 -133.3(11) . . . 7_535 ?
C10S C9 C14S C13S 1(2) . . . . ?
C10S C9 C14 C13 65.9(16) . . . . ?
C10S C9 C10 C11 -59.7(16) . . . . ?
C10S C11S C12S C13S -6(4) . . . . ?
C14 C9 C1 C2 -39.7(14) . . . . ?
C14 C9 C1 C8 142.2(11) . . . 7_535 ?
C14 C9 C14S C13S 58.3(17) . . . . ?
C14 C9 C10S C11S -59.8(18) . . . . ?
C14 C9 C10 C11 -1(2) . . . . ?
C14 C13 C12 C11 2(3) . . . . ?
C10 C9 C1 C2 138.1(11) . . . . ?
C10 C9 C1 C8 -40.0(13) . . . 7_535 ?
C10 C9 C14S C13S -66.4(17) . . . . ?
C10 C9 C10S C11S 66.1(19) . . . . ?
C10 C9 C14 C13 2(2) . . . . ?
C10 C11 C12 C13 -1(3) . . . . ?
Br C6 C5 C4 -176.8(6) . . . . ?
Br C6 C7 C8 177.3(6) . . . . ?
Br1S C6 C5 C4 -145.7(9) . . . . ?
Br1S C6 C7 C8 145.7(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4000s
_database_code_depnum_ccdc_archive 'CCDC 1496150'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;
_audit_creation_date             2015-03-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        jm192.1
_chemical_formula_moiety         'C36 H32 Br2'
_chemical_formula_sum            'C36 H32 Br2'
_chemical_formula_weight         624.43
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0648(5)
_cell_length_b                   11.6684(6)
_cell_length_c                   12.2462(6)
_cell_angle_alpha                77.981(2)
_cell_angle_beta                 86.017(2)
_cell_angle_gamma                79.287(2)
_cell_volume                     1381.44(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6467
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.97
_shelx_estimated_absorpt_T_max   0.916
_shelx_estimated_absorpt_T_min   0.603
_exptl_absorpt_coefficient_mu    2.958
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5911
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0999 before and 0.0426 after correction.
The Ratio of minimum to maximum transmission is 0.7924.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear yellowish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             636
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23414
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         2.630
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker X8-KappaApexII'
_diffrn_measurement_method       'fine slicing ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5052
_reflns_number_total             6547
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.471
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         6547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0765P)²+1.2445P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1396
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(Br1S)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
 Sof(Br2S)=1-FVAR(2)
 Sof(Br2)=FVAR(2)
3.a Aromatic/amide H refined with riding coordinates:
 C26(H26), C32(H32), C28(H28), C6(H6), C2(H2), C29(H29), C11(H11), C23(H23),
 C15(H15), C5(H5), C24(H24), C14(H14), C12(H12), C31(H31)
3.b Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C18(H18A,H18B,H18C), C35(H35A,H35B,H35C), C19(H19A,H19B,
 H19C), C34(H34A,H34B,H34C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.80237(4) -0.00465(3) 0.14257(3) 0.02678(13) Uani 0.8963(14) 1 d . . P
A 1
Br2 Br 1.06251(4) -0.36152(3) 1.14525(3) 0.02901(14) Uani 0.9010(15) 1 d . . P
B 1
C1 C 0.8323(4) -0.0355(3) 0.2986(3) 0.0290(8) Uani 1 1 d . . . A 1
C25 C 1.0517(4) -0.3237(3) 0.9867(3) 0.0299(8) Uani 1 1 d . . . B 1
C30 C 0.5762(3) 0.1701(3) 0.8557(3) 0.0255(7) Uani 1 1 d . . . . .
C22 C 0.8743(3) -0.1009(3) 0.7449(3) 0.0264(7) Uani 1 1 d . . . . .
C13 C 1.3020(3) -0.5422(3) 0.4327(3) 0.0269(7) Uani 1 1 d . . . . .
C21 C 0.9603(3) -0.1993(3) 0.8199(3) 0.0252(7) Uani 1 1 d . . . . .
C7 C 1.0265(3) -0.2508(3) 0.5349(3) 0.0263(7) Uani 1 1 d . . . . .
C27 C 0.7746(4) -0.0043(3) 0.7810(3) 0.0278(7) Uani 1 1 d . . . . .
C8 C 1.0011(3) -0.2295(3) 0.6403(3) 0.0260(7) Uani 1 1 d . . . . .
C26 C 0.9647(3) -0.2220(3) 0.9351(3) 0.0276(7) Uani 1 1 d . . . . .
H26 H 0.9104 -0.1703 0.9777 0.033 Uiso 1 1 calc R . . B .
C3 C 0.9391(3) -0.1520(3) 0.4616(3) 0.0251(7) Uani 1 1 d . . . . .
C10 C 1.1203(4) -0.3501(3) 0.4982(3) 0.0269(7) Uani 1 1 d . . . . .
C16 C 1.3986(4) -0.6431(3) 0.3906(3) 0.0288(8) Uani 1 1 d . . . . .
C9 C 0.9031(3) -0.1219(3) 0.6420(3) 0.0259(7) Uani 1 1 d . . . . .
C32 C 0.6434(4) 0.0234(3) 0.7407(3) 0.0319(8) Uani 1 1 d . . . . .
H32 H 0.6205 -0.0170 0.6867 0.038 Uiso 1 1 calc R . . . .
C20 C 1.0395(3) -0.2790(3) 0.7573(3) 0.0246(7) Uani 1 1 d . . . . .
C28 C 0.8068(4) 0.0588(3) 0.8555(3) 0.0291(7) Uani 1 1 d . . . . .
H28 H 0.8959 0.0430 0.8826 0.035 Uiso 1 1 calc R . . . .
C33 C 0.4669(4) 0.2523(3) 0.9100(3) 0.0280(7) Uani 1 1 d . . . . .
C36 C 0.3472(4) 0.3076(3) 0.8340(3) 0.0340(8) Uani 1 1 d . . . . .
H36A H 0.3801 0.3502 0.7626 0.051 Uiso 1 1 calc GR . . . .
H36B H 0.2831 0.3635 0.8702 0.051 Uiso 1 1 calc GR . . . .
H36C H 0.3018 0.2447 0.8207 0.051 Uiso 1 1 calc GR . . . .
C6 C 0.7608(4) 0.0455(3) 0.3577(3) 0.0316(8) Uani 1 1 d . . . . .
H6 H 0.7011 0.1132 0.3206 0.038 Uiso 1 1 calc R . . A 1
C2 C 0.9218(3) -0.1355(3) 0.3483(3) 0.0261(7) Uani 1 1 d . . . . .
H2 H 0.9693 -0.1905 0.3057 0.031 Uiso 1 1 calc R . . A .
C29 C 0.7097(4) 0.1457(3) 0.8913(3) 0.0295(8) Uani 1 1 d . . . . .
H29 H 0.7346 0.1898 0.9412 0.035 Uiso 1 1 calc R . . . .
C11 C 1.2033(4) -0.3304(3) 0.4038(3) 0.0311(8) Uani 1 1 d . . . . .
H11 H 1.1993 -0.2522 0.3606 0.037 Uiso 1 1 calc R . . . .
C4 C 0.8638(4) -0.0714(3) 0.5242(3) 0.0260(7) Uani 1 1 d . . . . .
C23 C 1.1267(3) -0.3773(3) 0.8121(3) 0.0292(8) Uani 1 1 d . . . . .
H23 H 1.1819 -0.4297 0.7707 0.035 Uiso 1 1 calc R . . . .
C15 C 1.1297(4) -0.4673(3) 0.5603(3) 0.0308(8) Uani 1 1 d . . . . .
H15 H 1.0746 -0.4824 0.6260 0.037 Uiso 1 1 calc R . . . .
C18 C 1.5385(4) -0.6087(3) 0.3614(4) 0.0368(9) Uani 1 1 d . . . . .
H18A H 1.5303 -0.5365 0.3029 0.055 Uiso 1 1 calc GR . . . .
H18B H 1.5992 -0.6738 0.3345 0.055 Uiso 1 1 calc GR . . . .
H18C H 1.5756 -0.5939 0.4280 0.055 Uiso 1 1 calc GR . . . .
C5 C 0.7767(4) 0.0273(3) 0.4719(3) 0.0292(8) Uani 1 1 d . . . . .
H5 H 0.7280 0.0824 0.5138 0.035 Uiso 1 1 calc R . . . .
C35 C 0.5241(4) 0.3534(3) 0.9441(4) 0.0370(9) Uani 1 1 d . . . . .
H35A H 0.5849 0.3200 1.0063 0.056 Uiso 1 1 calc GR . . . .
H35B H 0.4494 0.4111 0.9672 0.056 Uiso 1 1 calc GR . . . .
H35C H 0.5742 0.3932 0.8803 0.056 Uiso 1 1 calc GR . . . .
C24 C 1.1330(4) -0.3986(3) 0.9267(3) 0.0316(8) Uani 1 1 d . . . . .
H24 H 1.1936 -0.4652 0.9644 0.038 Uiso 1 1 calc R . . B 1
C14 C 1.2183(4) -0.5610(3) 0.5270(3) 0.0301(8) Uani 1 1 d . . . . .
H14 H 1.2215 -0.6393 0.5697 0.036 Uiso 1 1 calc R . . . .
C12 C 1.2923(4) -0.4246(3) 0.3721(3) 0.0310(8) Uani 1 1 d . . . . .
H12 H 1.3488 -0.4091 0.3073 0.037 Uiso 1 1 calc R . . . .
C19 C 1.4182(4) -0.7593(3) 0.4787(4) 0.0397(9) Uani 1 1 d . . . . .
H19A H 1.4609 -0.7471 0.5440 0.059 Uiso 1 1 calc GR . . . .
H19B H 1.4762 -0.8223 0.4471 0.059 Uiso 1 1 calc GR . . . .
H19C H 1.3300 -0.7824 0.5014 0.059 Uiso 1 1 calc GR . . . .
C31 C 0.5454(4) 0.1094(3) 0.7784(3) 0.0322(8) Uani 1 1 d . . . . .
H31 H 0.4567 0.1261 0.7504 0.039 Uiso 1 1 calc R . . . .
C34 C 0.4153(4) 0.1769(4) 1.0171(3) 0.0384(9) Uani 1 1 d . . . . .
H34A H 0.3818 0.1098 0.9986 0.058 Uiso 1 1 calc GR . . . .
H34B H 0.3417 0.2260 1.0520 0.058 Uiso 1 1 calc GR . . . .
H34C H 0.4894 0.1467 1.0691 0.058 Uiso 1 1 calc GR . . . .
C17 C 1.3390(4) -0.6642(4) 0.2857(4) 0.0435(10) Uani 1 1 d . . . . .
H17A H 1.2512 -0.6893 0.3052 0.065 Uiso 1 1 calc GR . . . .
H17B H 1.4007 -0.7265 0.2558 0.065 Uiso 1 1 calc GR . . . .
H17C H 1.3270 -0.5904 0.2292 0.065 Uiso 1 1 calc GR . . . .
Br1S Br 0.6800(4) 0.1279(3) 0.2069(3) 0.0352(12) Uiso 0.1037(14) 1 d . . P A 2
Br2S Br 1.1793(4) -0.4960(4) 1.0761(3) 0.0400(13) Uiso 0.0990(15) 1 d . . P B 2


_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
Br1 C1 1.904(3) . ?
Br2 C25 1.906(3) . ?
C1 C6 1.377(5) . ?
C1 C2 1.391(5) . ?
C25 C26 1.397(5) . ?
C25 C24 1.375(5) . ?
C30 C33 1.530(4) . ?
C30 C29 1.401(5) . ?
C30 C31 1.377(5) . ?
C22 C21 1.488(5) . ?
C22 C27 1.482(5) . ?
C22 C9 1.337(5) . ?
C13 C16 1.535(4) . ?
C13 C14 1.385(5) . ?
C13 C12 1.407(5) . ?
C21 C26 1.382(5) . ?
C21 C20 1.423(5) . ?
C7 C8 1.362(5) . ?
C7 C3 1.486(5) . ?
C7 C10 1.479(5) . ?
C27 C32 1.399(5) . ?
C27 C28 1.374(5) . ?
C8 C9 1.448(5) . ?
C8 C20 1.479(5) . ?
C26 H26 0.9500 . ?
C3 C2 1.380(5) . ?
C3 C4 1.415(5) . ?
C10 C11 1.383(5) . ?
C10 C15 1.409(5) . ?
C16 C18 1.534(5) . ?
C16 C19 1.537(5) . ?
C16 C17 1.538(5) . ?
C9 C4 1.491(5) . ?
C32 H32 0.9500 . ?
C32 C31 1.399(5) . ?
C20 C23 1.387(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.390(5) . ?
C33 C36 1.533(5) . ?
C33 C35 1.545(5) . ?
C33 C34 1.537(5) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C6 H6 0.9500 . ?
C6 C5 1.386(5) . ?
C6 Br1S 2.043(5) . ?
C2 H2 0.9500 . ?
C29 H29 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.387(5) . ?
C4 C5 1.378(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.377(5) . ?
C15 H15 0.9500 . ?
C15 C14 1.388(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C5 H5 0.9500 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C24 H24 0.9500 . ?
C24 Br2S 1.978(6) . ?
C14 H14 0.9500 . ?
C12 H12 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C31 H31 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 Br1 116.5(3) . . ?
C6 C1 C2 122.8(3) . . ?
C2 C1 Br1 120.7(3) . . ?
C26 C25 Br2 120.1(3) . . ?
C24 C25 Br2 117.7(3) . . ?
C24 C25 C26 122.2(3) . . ?
C29 C30 C33 120.5(3) . . ?
C31 C30 C33 121.7(3) . . ?
C31 C30 C29 117.6(3) . . ?
C27 C22 C21 125.8(3) . . ?
C9 C22 C21 105.4(3) . . ?
C9 C22 C27 128.8(3) . . ?
C14 C13 C16 123.2(3) . . ?
C14 C13 C12 117.1(3) . . ?
C12 C13 C16 119.7(3) . . ?
C26 C21 C22 128.7(3) . . ?
C26 C21 C20 120.6(3) . . ?
C20 C21 C22 110.6(3) . . ?
C8 C7 C3 105.5(3) . . ?
C8 C7 C10 128.5(3) . . ?
C10 C7 C3 126.0(3) . . ?
C32 C27 C22 120.1(3) . . ?
C28 C27 C22 121.6(3) . . ?
C28 C27 C32 118.3(3) . . ?
C7 C8 C9 111.9(3) . . ?
C7 C8 C20 141.7(3) . . ?
C9 C8 C20 106.4(3) . . ?
C25 C26 H26 121.2 . . ?
C21 C26 C25 117.6(3) . . ?
C21 C26 H26 121.2 . . ?
C2 C3 C7 128.6(3) . . ?
C2 C3 C4 120.3(3) . . ?
C4 C3 C7 111.1(3) . . ?
C11 C10 C7 121.2(3) . . ?
C11 C10 C15 118.1(3) . . ?
C15 C10 C7 120.7(3) . . ?
C13 C16 C19 112.2(3) . . ?
C13 C16 C17 108.1(3) . . ?
C18 C16 C13 110.3(3) . . ?
C18 C16 C19 107.3(3) . . ?
C18 C16 C17 109.6(3) . . ?
C19 C16 C17 109.4(3) . . ?
C22 C9 C8 112.9(3) . . ?
C22 C9 C4 140.3(3) . . ?
C8 C9 C4 106.8(3) . . ?
C27 C32 H32 119.4 . . ?
C31 C32 C27 121.1(3) . . ?
C31 C32 H32 119.4 . . ?
C21 C20 C8 104.7(3) . . ?
C23 C20 C21 119.6(3) . . ?
C23 C20 C8 135.8(3) . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.3(3) . . ?
C29 C28 H28 119.8 . . ?
C30 C33 C36 112.5(3) . . ?
C30 C33 C35 111.8(3) . . ?
C30 C33 C34 107.4(3) . . ?
C36 C33 C35 108.7(3) . . ?
C36 C33 C34 108.8(3) . . ?
C34 C33 C35 107.5(3) . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C1 C6 H6 120.4 . . ?
C1 C6 C5 119.3(3) . . ?
C5 C6 H6 120.4 . . ?
C5 C6 Br1S 156.4(3) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.6(3) . . ?
C3 C2 H2 121.2 . . ?
C30 C29 H29 119.1 . . ?
C28 C29 C30 121.9(3) . . ?
C28 C29 H29 119.1 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C3 C4 C9 104.7(3) . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 C9 134.9(3) . . ?
C20 C23 H23 120.1 . . ?
C24 C23 C20 119.7(3) . . ?
C24 C23 H23 120.1 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.1(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 H5 120.2 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C25 C24 C23 120.1(3) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 Br2S 155.2(3) . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C13 C12 H12 118.8 . . ?
C11 C12 C13 122.3(3) . . ?
C11 C12 H12 118.8 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C30 C31 C32 120.7(4) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C6 C5 179.2(3) . . . . ?
Br1 C1 C6 Br1S 1.2(3) . . . . ?
Br1 C1 C2 C3 179.7(3) . . . . ?
Br2 C25 C26 C21 -179.6(3) . . . . ?
Br2 C25 C24 C23 178.3(3) . . . . ?
Br2 C25 C24 Br2S 5.6(3) . . . . ?
C1 C6 C5 C4 0.0(5) . . . . ?
C22 C21 C26 C25 177.7(3) . . . . ?
C22 C21 C20 C8 -0.4(4) . . . . ?
C22 C21 C20 C23 -179.9(3) . . . . ?
C22 C27 C32 C31 176.3(3) . . . . ?
C22 C27 C28 C29 -177.4(3) . . . . ?
C22 C9 C4 C3 -177.3(5) . . . . ?
C22 C9 C4 C5 2.0(8) . . . . ?
C21 C22 C27 C32 -130.9(4) . . . . ?
C21 C22 C27 C28 48.0(5) . . . . ?
C21 C22 C9 C8 1.2(4) . . . . ?
C21 C22 C9 C4 179.0(4) . . . . ?
C21 C20 C23 C24 1.8(5) . . . . ?
C7 C8 C9 C22 178.5(3) . . . . ?
C7 C8 C9 C4 -0.1(4) . . . . ?
C7 C8 C20 C21 -178.8(5) . . . . ?
C7 C8 C20 C23 0.5(8) . . . . ?
C7 C3 C2 C1 179.3(3) . . . . ?
C7 C3 C4 C9 -0.9(4) . . . . ?
C7 C3 C4 C5 179.7(3) . . . . ?
C7 C10 C11 C12 178.7(3) . . . . ?
C7 C10 C15 C14 -179.4(3) . . . . ?
C27 C22 C21 C26 0.8(6) . . . . ?
C27 C22 C21 C20 177.3(3) . . . . ?
C27 C22 C9 C8 -176.5(3) . . . . ?
C27 C22 C9 C4 1.4(7) . . . . ?
C27 C32 C31 C30 0.7(6) . . . . ?
C27 C28 C29 C30 1.7(5) . . . . ?
C8 C7 C3 C2 -176.3(3) . . . . ?
C8 C7 C3 C4 0.9(4) . . . . ?
C8 C7 C10 C11 -136.5(4) . . . . ?
C8 C7 C10 C15 41.9(6) . . . . ?
C8 C9 C4 C3 0.6(4) . . . . ?
C8 C9 C4 C5 179.9(4) . . . . ?
C8 C20 C23 C24 -177.5(4) . . . . ?
C26 C25 C24 C23 -2.5(6) . . . . ?
C26 C25 C24 Br2S -175.2(3) . . . . ?
C26 C21 C20 C8 176.4(3) . . . . ?
C26 C21 C20 C23 -3.1(5) . . . . ?
C3 C7 C8 C9 -0.5(4) . . . . ?
C3 C7 C8 C20 179.4(4) . . . . ?
C3 C7 C10 C11 43.5(5) . . . . ?
C3 C7 C10 C15 -138.1(4) . . . . ?
C3 C4 C5 C6 1.6(5) . . . . ?
C10 C7 C8 C9 179.5(3) . . . . ?
C10 C7 C8 C20 -0.6(7) . . . . ?
C10 C7 C3 C2 3.7(6) . . . . ?
C10 C7 C3 C4 -179.0(3) . . . . ?
C10 C11 C12 C13 0.3(6) . . . . ?
C10 C15 C14 C13 1.0(6) . . . . ?
C16 C13 C14 C15 -178.2(3) . . . . ?
C16 C13 C12 C11 177.6(3) . . . . ?
C9 C22 C21 C26 -176.9(4) . . . . ?
C9 C22 C21 C20 -0.4(4) . . . . ?
C9 C22 C27 C32 46.3(6) . . . . ?
C9 C22 C27 C28 -134.8(4) . . . . ?
C9 C8 C20 C21 1.1(4) . . . . ?
C9 C8 C20 C23 -179.6(4) . . . . ?
C9 C4 C5 C6 -177.6(4) . . . . ?
C32 C27 C28 C29 1.5(5) . . . . ?
C20 C21 C26 C25 1.6(5) . . . . ?
C20 C8 C9 C22 -1.5(4) . . . . ?
C20 C8 C9 C4 180.0(3) . . . . ?
C20 C23 C24 C25 0.9(6) . . . . ?
C20 C23 C24 Br2S 163.3(6) . . . . ?
C28 C27 C32 C31 -2.7(5) . . . . ?
C33 C30 C29 C28 170.6(3) . . . . ?
C33 C30 C31 C32 -171.7(3) . . . . ?
C6 C1 C2 C3 -0.6(5) . . . . ?
C2 C1 C6 C5 -0.6(5) . . . . ?
C2 C1 C6 Br1S -178.6(3) . . . . ?
C2 C3 C4 C9 176.6(3) . . . . ?
C2 C3 C4 C5 -2.8(5) . . . . ?
C29 C30 C33 C36 157.0(3) . . . . ?
C29 C30 C33 C35 34.4(5) . . . . ?
C29 C30 C33 C34 -83.3(4) . . . . ?
C29 C30 C31 C32 2.4(5) . . . . ?
C11 C10 C15 C14 -1.0(5) . . . . ?
C4 C3 C2 C1 2.2(5) . . . . ?
C15 C10 C11 C12 0.3(5) . . . . ?
C24 C25 C26 C21 1.2(5) . . . . ?
C14 C13 C16 C18 -133.9(4) . . . . ?
C14 C13 C16 C19 -14.4(5) . . . . ?
C14 C13 C16 C17 106.2(4) . . . . ?
C14 C13 C12 C11 -0.3(5) . . . . ?
C12 C13 C16 C18 48.3(5) . . . . ?
C12 C13 C16 C19 167.9(3) . . . . ?
C12 C13 C16 C17 -71.5(4) . . . . ?
C12 C13 C14 C15 -0.4(5) . . . . ?
C31 C30 C33 C36 -28.9(5) . . . . ?
C31 C30 C33 C35 -151.6(3) . . . . ?
C31 C30 C33 C34 90.7(4) . . . . ?
C31 C30 C29 C28 -3.6(5) . . . . ?
Br1S C6 C5 C4 175.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_4375n
_database_code_depnum_ccdc_archive 'CCDC 1496151'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;
_audit_creation_date             2016-07-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H28 Br2'
_chemical_formula_sum            'C34 H28 Br2'
_chemical_formula_weight         596.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.1310(4)
_cell_length_b                   10.2490(3)
_cell_length_c                   11.7630(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.301(2)
_cell_angle_gamma                90
_cell_volume                     1315.92(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7193
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.59
_cell_measurement_theta_min      5.00
_shelx_estimated_absorpt_T_max   0.923
_shelx_estimated_absorpt_T_min   0.642
_exptl_absorpt_coefficient_mu    4.054
_exptl_absorpt_correction_T_max  0.4551
_exptl_absorpt_correction_T_min  0.1532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1824 before and 0.1161 after correction.
The Ratio of minimum to maximum transmission is 0.3366.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1700
_diffrn_reflns_av_unetI/netI     0.0991
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11321
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.439
_diffrn_reflns_theta_max         67.439
_diffrn_reflns_theta_min         5.003
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon100 detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1742
_reflns_number_total             2298
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.863
_refine_diff_density_min         -0.898
_refine_diff_density_rms         0.149
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0691
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0381P)²+11.5874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1474
_refine_ls_wR_factor_ref         0.1648
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C11(H11), C13(H13)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.65935(7) 0.07277(6) 0.63914(8) 0.0297(3) Uani 1 1 d . . . . .
C1 C 0.7848(6) 0.1944(6) 0.6195(7) 0.0260(17) Uani 1 1 d . . . . .
C2 C 0.8987(6) 0.1805(6) 0.6860(6) 0.0242(16) Uani 1 1 d . . . . .
H2 H 0.9146 0.1130 0.7422 0.029 Uiso 1 1 calc R . . . .
C3 C 0.9930(6) 0.2668(6) 0.6711(7) 0.0258(16) Uani 1 1 d . . . . .
H3 H 1.0730 0.2585 0.7170 0.031 Uiso 1 1 calc R . . . .
C4 C 0.9667(5) 0.3640(6) 0.5882(6) 0.0206(15) Uani 1 1 d . . . . .
C5 C 1.0407(5) 0.4651(6) 0.5470(6) 0.0200(15) Uani 1 1 d . . . . .
C6 C 1.1564(5) 0.5141(6) 0.5649(6) 0.0190(15) Uani 1 1 d . . . . .
C7 C 1.1532(6) 0.6230(6) 0.4788(6) 0.0197(15) Uani 1 1 d . . . . .
C8 C 1.2453(6) 0.7088(6) 0.4669(6) 0.0223(15) Uani 1 1 d . . . . .
H8 H 1.3248 0.7032 0.5143 0.027 Uiso 1 1 calc R . . . .
C9 C 1.2662(6) 0.4685(6) 0.6466(6) 0.0190(15) Uani 1 1 d . . . . .
C10 C 1.3630(5) 0.4114(5) 0.6044(6) 0.0174(14) Uani 1 1 d . . . . .
C11 C 1.4647(5) 0.3655(5) 0.6831(6) 0.0203(16) Uani 1 1 d . . . . .
H11 H 1.5308 0.3274 0.6545 0.024 Uiso 1 1 calc R . . . .
C12 C 1.4719(5) 0.3740(6) 0.8020(6) 0.0179(15) Uani 1 1 d . . . . .
C13 C 1.3756(6) 0.4307(6) 0.8408(6) 0.0191(14) Uani 1 1 d . . . . .
H13 H 1.3791 0.4366 0.9220 0.023 Uiso 1 1 calc R . . . .
C14 C 1.2732(6) 0.4798(6) 0.7661(6) 0.0204(15) Uani 1 1 d . . . . .
C15 C 1.3588(6) 0.3907(6) 0.4776(6) 0.0203(15) Uani 1 1 d . . . . .
H15A H 1.2733 0.3861 0.4367 0.030 Uiso 1 1 calc GR . . . .
H15B H 1.4005 0.3089 0.4662 0.030 Uiso 1 1 calc GR . . . .
H15C H 1.3998 0.4635 0.4468 0.030 Uiso 1 1 calc GR . . . .
C16 C 1.5819(6) 0.3199(6) 0.8824(7) 0.0276(17) Uani 1 1 d . . . . .
H16A H 1.5786 0.2243 0.8806 0.041 Uiso 1 1 calc GR . . . .
H16B H 1.5826 0.3504 0.9615 0.041 Uiso 1 1 calc GR . . . .
H16C H 1.6565 0.3494 0.8577 0.041 Uiso 1 1 calc GR . . . .
C17 C 1.1730(7) 0.5449(7) 0.8163(7) 0.0319(18) Uani 1 1 d . . . . .
H17A H 1.1482 0.6262 0.7742 0.048 Uiso 1 1 calc GR . . . .
H17B H 1.2036 0.5644 0.8984 0.048 Uiso 1 1 calc GR . . . .
H17C H 1.1023 0.4863 0.8087 0.048 Uiso 1 1 calc GR . . . .


_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
Br C1 1.920(7) . ?
C1 C2 1.360(9) . ?
C1 C8 1.413(10) 3_766 ?
C2 H2 0.9500 . ?
C2 C3 1.410(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(9) . ?
C4 C5 1.464(9) . ?
C4 C7 1.417(8) 3_766 ?
C5 C5 1.472(12) 3_766 ?
C5 C6 1.360(9) . ?
C6 C7 1.504(9) . ?
C6 C9 1.474(8) . ?
C7 C4 1.417(8) 3_766 ?
C7 C8 1.378(9) . ?
C8 C1 1.413(10) 3_766 ?
C8 H8 0.9500 . ?
C9 C10 1.400(9) . ?
C9 C14 1.398(10) . ?
C10 C11 1.396(9) . ?
C10 C15 1.498(9) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(10) . ?
C12 C13 1.374(9) . ?
C12 C16 1.499(9) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(9) . ?
C14 C17 1.516(9) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br 118.7(5) . . ?
C2 C1 C8 123.4(6) . 3_766 ?
C8 C1 Br 117.8(5) 3_766 . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.7(6) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.6(6) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C5 133.4(6) . . ?
C3 C4 C7 120.4(6) . 3_766 ?
C7 C4 C5 106.2(5) 3_766 . ?
C4 C5 C5 106.8(6) . 3_766 ?
C6 C5 C4 142.0(6) . . ?
C6 C5 C5 111.2(7) . 3_766 ?
C5 C6 C7 105.9(5) . . ?
C5 C6 C9 128.5(6) . . ?
C9 C6 C7 125.6(5) . . ?
C4 C7 C6 109.9(5) 3_766 . ?
C8 C7 C4 121.5(6) . 3_766 ?
C8 C7 C6 128.4(6) . . ?
C1 C8 H8 121.8 3_766 . ?
C7 C8 C1 116.3(6) . 3_766 ?
C7 C8 H8 121.8 . . ?
C10 C9 C6 119.9(6) . . ?
C14 C9 C6 120.4(6) . . ?
C14 C9 C10 119.7(6) . . ?
C9 C10 C15 122.4(6) . . ?
C11 C10 C9 119.1(6) . . ?
C11 C10 C15 118.4(6) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.8(6) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 C16 119.4(6) . . ?
C13 C12 C11 117.8(6) . . ?
C13 C12 C16 122.8(6) . . ?
C12 C13 H13 118.7 . . ?
C12 C13 C14 122.7(6) . . ?
C14 C13 H13 118.7 . . ?
C9 C14 C17 121.9(6) . . ?
C13 C14 C9 118.9(6) . . ?
C13 C14 C17 119.2(6) . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br C1 C2 C3 178.5(5) . . . . ?
C1 C2 C3 C4 -0.1(10) . . . . ?
C2 C3 C4 C5 -177.4(7) . . . . ?
C2 C3 C4 C7 0.9(10) . . . 3_766 ?
C3 C4 C5 C5 177.6(8) . . . 3_766 ?
C3 C4 C5 C6 -1.4(16) . . . . ?
C4 C5 C6 C7 179.2(9) . . . . ?
C4 C5 C6 C9 2.0(15) . . . . ?
C4 C7 C8 C1 -3.2(10) 3_766 . . 3_766 ?
C5 C5 C6 C7 0.2(9) 3_766 . . . ?
C5 C5 C6 C9 -177.0(7) 3_766 . . . ?
C5 C6 C7 C4 0.4(8) . . . 3_766 ?
C5 C6 C7 C8 175.3(7) . . . . ?
C5 C6 C9 C10 111.8(8) . . . . ?
C5 C6 C9 C14 -67.0(9) . . . . ?
C6 C7 C8 C1 -177.6(6) . . . 3_766 ?
C6 C9 C10 C11 -178.2(5) . . . . ?
C6 C9 C10 C15 -1.8(9) . . . . ?
C6 C9 C14 C13 177.2(5) . . . . ?
C6 C9 C14 C17 -3.3(9) . . . . ?
C7 C4 C5 C5 -0.9(9) 3_766 . . 3_766 ?
C7 C4 C5 C6 -179.9(9) 3_766 . . . ?
C7 C6 C9 C10 -64.8(9) . . . . ?
C7 C6 C9 C14 116.4(7) . . . . ?
C8 C1 C2 C3 1.0(11) 3_766 . . . ?
C9 C6 C7 C4 177.6(6) . . . 3_766 ?
C9 C6 C7 C8 -7.4(11) . . . . ?
C9 C10 C11 C12 0.5(9) . . . . ?
C10 C9 C14 C13 -1.6(9) . . . . ?
C10 C9 C14 C17 177.9(6) . . . . ?
C10 C11 C12 C13 -0.7(9) . . . . ?
C10 C11 C12 C16 178.4(5) . . . . ?
C11 C12 C13 C14 -0.4(9) . . . . ?
C12 C13 C14 C9 1.6(9) . . . . ?
C12 C13 C14 C17 -178.0(6) . . . . ?
C14 C9 C10 C11 0.6(9) . . . . ?
C14 C9 C10 C15 177.1(6) . . . . ?
C15 C10 C11 C12 -176.1(5) . . . . ?
C16 C12 C13 C14 -179.4(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_4418f
_database_code_depnum_ccdc_archive 'CCDC 1496152'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;
_audit_creation_date             2016-01-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.21 svn.r3230 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        jm245.3b
_chemical_formula_moiety         '2(C25 H19)'
_chemical_formula_sum            'C50 H38'
_chemical_formula_weight         638.80
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8252(8)
_cell_length_b                   13.5794(10)
_cell_length_c                   14.2122(10)
_cell_angle_alpha                114.377(4)
_cell_angle_beta                 91.316(5)
_cell_angle_gamma                95.604(4)
_cell_volume                     1889.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9181
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.18
_cell_measurement_theta_min      3.42
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.478
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4290
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1615 before and 0.1109 after correction.
The Ratio of minimum to maximum transmission is 0.5695.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             676
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1028
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35349
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.700
_diffrn_reflns_theta_min         3.422
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon100 detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8-Venture'
_diffrn_measurement_method       'fine slicing ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4647
_reflns_number_total             6591
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         6591
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1377
_refine_ls_R_factor_gt           0.1086
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0898P)²+6.5468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2590
_refine_ls_wR_factor_ref         0.2735
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C13(H13), C14(H14),
 C19(H19), C21(H21), C2'(H2'), C3'(H3'), C4'(H4'), C5'(H5'), C6'(H6'),
 C10'(H10'), C13'(H13'), C14'(H14'), C19'(H19'), C21'(H21')
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C23'(H23D,H23E,
 H23F), C24'(H24D,H24E,H24F), C25'(H25D,H25E,H25F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4002(4) 0.0994(4) 0.1137(4) 0.0309(10) Uani 1 1 d . . . . .
C2 C 0.4155(5) 0.1100(4) 0.0205(4) 0.0368(11) Uani 1 1 d . . . . .
H2 H 0.4844 0.1561 0.0153 0.044 Uiso 1 1 calc R . . . .
C3 C 0.3323(5) 0.0547(4) -0.0628(4) 0.0423(13) Uani 1 1 d . . . . .
H3 H 0.3432 0.0627 -0.1255 0.051 Uiso 1 1 calc R . . . .
C4 C 0.2300(6) -0.0143(4) -0.0558(4) 0.0457(14) Uani 1 1 d . . . . .
H4 H 0.1730 -0.0539 -0.1143 0.055 Uiso 1 1 calc R . . . .
C5 C 0.2132(5) -0.0240(4) 0.0347(4) 0.0430(13) Uani 1 1 d . . . . .
H5 H 0.1428 -0.0684 0.0403 0.052 Uiso 1 1 calc R . . . .
C6 C 0.3001(5) 0.0316(4) 0.1200(4) 0.0324(11) Uani 1 1 d . . . . .
H6 H 0.2899 0.0225 0.1822 0.039 Uiso 1 1 calc R . . . .
C7 C 0.4889(5) 0.1572(4) 0.1989(4) 0.0304(10) Uani 1 1 d . . . . .
C8 C 0.5664(4) 0.2081(4) 0.2683(3) 0.0298(10) Uani 1 1 d . . . . .
C9 C 0.6641(4) 0.2795(3) 0.3443(3) 0.0262(9) Uani 1 1 d . . . . .
C10 C 0.7710(4) 0.3162(3) 0.3092(3) 0.0266(10) Uani 1 1 d . . . . .
H10 H 0.7800 0.2931 0.2372 0.032 Uiso 1 1 calc R . . . .
C11 C 0.8629(4) 0.3863(3) 0.3804(3) 0.0235(9) Uani 1 1 d . . . . .
C12 C 0.8492(4) 0.4232(3) 0.4887(3) 0.0243(9) Uani 1 1 d . . . . .
C13 C 0.7431(4) 0.3866(4) 0.5224(3) 0.0273(10) Uani 1 1 d . . . . .
H13 H 0.7331 0.4103 0.5944 0.033 Uiso 1 1 calc R . . . .
C14 C 0.6508(4) 0.3144(3) 0.4499(3) 0.0265(9) Uani 1 1 d . . . . .
H14 H 0.5780 0.2887 0.4730 0.032 Uiso 1 1 calc R . . . .
C15 C 0.9610(4) 0.4977(3) 0.5405(3) 0.0249(9) Uani 1 1 d . . . . .
C16 C 1.0159(4) 0.5634(3) 0.6359(3) 0.0241(9) Uani 1 1 d . . . . .
C17 C 0.9697(4) 0.5844(3) 0.7394(3) 0.0245(9) Uani 1 1 d . . . . .
C18 C 0.9651(4) 0.5023(4) 0.7759(3) 0.0274(10) Uani 1 1 d . . . . .
C19 C 0.9228(4) 0.5240(4) 0.8734(3) 0.0295(10) Uani 1 1 d . . . . .
H19 H 0.9187 0.4686 0.8981 0.035 Uiso 1 1 calc R . . . .
C20 C 0.8863(4) 0.6253(4) 0.9359(3) 0.0302(10) Uani 1 1 d . . . . .
C21 C 0.8944(4) 0.7056(4) 0.8986(3) 0.0314(10) Uani 1 1 d . . . . .
H21 H 0.8716 0.7754 0.9412 0.038 Uiso 1 1 calc R . . . .
C22 C 0.9344(4) 0.6871(3) 0.8015(3) 0.0247(9) Uani 1 1 d . . . . .
C23 C 1.0053(5) 0.3919(4) 0.7125(4) 0.0358(12) Uani 1 1 d . . . . .
H23A H 0.9527 0.3561 0.6477 0.054 Uiso 1 1 calc GR . . . .
H23B H 0.9971 0.3471 0.7518 0.054 Uiso 1 1 calc GR . . . .
H23C H 1.0923 0.4006 0.6968 0.054 Uiso 1 1 calc GR . . . .
C24 C 0.8411(6) 0.6486(5) 1.0418(4) 0.0469(14) Uani 1 1 d . . . . .
H24A H 0.8575 0.5896 1.0614 0.070 Uiso 1 1 calc GR . . . .
H24B H 0.7515 0.6537 1.0404 0.070 Uiso 1 1 calc GR . . . .
H24C H 0.8849 0.7175 1.0925 0.070 Uiso 1 1 calc GR . . . .
C25 C 0.9364(5) 0.7762(4) 0.7650(4) 0.0319(11) Uani 1 1 d . . . . .
H25A H 1.0046 0.7708 0.7196 0.048 Uiso 1 1 calc GR . . . .
H25B H 0.9486 0.8470 0.8249 0.048 Uiso 1 1 calc GR . . . .
H25C H 0.8571 0.7690 0.7267 0.048 Uiso 1 1 calc GR . . . .
C1' C 0.9695(4) 0.0292(3) -0.3062(3) 0.0276(10) Uani 1 1 d . . . . .
C2' C 0.9183(5) -0.0433(4) -0.4038(4) 0.0418(13) Uani 1 1 d . . . . .
H2' H 0.8377 -0.0373 -0.4273 0.050 Uiso 1 1 calc R . . . .
C3' C 0.9869(5) -0.1254(4) -0.4672(4) 0.0450(13) Uani 1 1 d . . . . .
H3' H 0.9528 -0.1754 -0.5341 0.054 Uiso 1 1 calc R . . . .
C4' C 1.1011(5) -0.1336(4) -0.4334(4) 0.0401(12) Uani 1 1 d . . . . .
H4' H 1.1466 -0.1896 -0.4768 0.048 Uiso 1 1 calc R . . . .
C5' C 1.1530(5) -0.0616(4) -0.3367(4) 0.0391(12) Uani 1 1 d . . . . .
H5' H 1.2339 -0.0681 -0.3143 0.047 Uiso 1 1 calc R . . . .
C6' C 1.0867(4) 0.0205(4) -0.2721(4) 0.0311(10) Uani 1 1 d . . . . .
H6' H 1.1218 0.0699 -0.2054 0.037 Uiso 1 1 calc R . . . .
C7' C 0.8985(4) 0.1127(4) -0.2396(4) 0.0304(10) Uani 1 1 d . . . . .
C8' C 0.8398(5) 0.1808(3) -0.1835(3) 0.0298(10) Uani 1 1 d . . . . .
C9' C 0.7649(4) 0.2619(3) -0.1189(3) 0.0274(10) Uani 1 1 d . . . . .
C10' C 0.6733(4) 0.2962(3) -0.1665(3) 0.0256(10) Uani 1 1 d . . . . .
H10' H 0.6612 0.2666 -0.2398 0.031 Uiso 1 1 calc R . . . .
C11' C 0.6013(4) 0.3736(3) -0.1048(3) 0.0223(9) Uani 1 1 d . . . . .
C12' C 0.6222(4) 0.4184(3) 0.0055(3) 0.0252(9) Uani 1 1 d . . . . .
C13' C 0.7130(4) 0.3852(4) 0.0515(3) 0.0273(10) Uani 1 1 d . . . . .
H13' H 0.7263 0.4152 0.1248 0.033 Uiso 1 1 calc R . . . .
C14' C 0.7846(4) 0.3072(3) -0.0108(3) 0.0279(10) Uani 1 1 d . . . . .
H14' H 0.8479 0.2843 0.0203 0.033 Uiso 1 1 calc R . . . .
C15' C 0.5346(4) 0.4998(3) 0.0448(3) 0.0242(9) Uani 1 1 d . . . . .
C16' C 0.4982(4) 0.5754(3) 0.1345(3) 0.0236(9) Uani 1 1 d . . . . .
C17' C 0.5456(4) 0.6014(3) 0.2416(3) 0.0226(9) Uani 1 1 d . . . . .
C18' C 0.6169(4) 0.7016(4) 0.2990(3) 0.0278(10) Uani 1 1 d . . . . .
C19' C 0.6651(4) 0.7222(4) 0.3975(3) 0.0311(10) Uani 1 1 d . . . . .
H19' H 0.7124 0.7905 0.4373 0.037 Uiso 1 1 calc R . . . .
C20' C 0.6467(4) 0.6468(4) 0.4403(3) 0.0317(11) Uani 1 1 d . . . . .
C21' C 0.5722(4) 0.5487(4) 0.3811(3) 0.0300(10) Uani 1 1 d . . . . .
H21' H 0.5574 0.4965 0.4092 0.036 Uiso 1 1 calc R . . . .
C22' C 0.5194(4) 0.5250(3) 0.2835(3) 0.0262(9) Uani 1 1 d . . . . .
C23' C 0.6429(5) 0.7849(4) 0.2561(4) 0.0415(13) Uani 1 1 d . . . . .
H23D H 0.6619 0.7487 0.1835 0.062 Uiso 1 1 calc GR . . . .
H23E H 0.7141 0.8372 0.2960 0.062 Uiso 1 1 calc GR . . . .
H23F H 0.5697 0.8234 0.2608 0.062 Uiso 1 1 calc GR . . . .
C24' C 0.7013(5) 0.6715(5) 0.5459(4) 0.0463(14) Uani 1 1 d . . . . .
H24D H 0.6824 0.7435 0.5942 0.069 Uiso 1 1 calc GR . . . .
H24E H 0.7917 0.6709 0.5444 0.069 Uiso 1 1 calc GR . . . .
H24F H 0.6656 0.6164 0.5684 0.069 Uiso 1 1 calc GR . . . .
C25' C 0.4348(6) 0.4207(4) 0.2241(4) 0.0409(13) Uani 1 1 d . . . . .
H25D H 0.3600 0.4371 0.1958 0.061 Uiso 1 1 calc GR . . . .
H25E H 0.4110 0.3864 0.2706 0.061 Uiso 1 1 calc GR . . . .
H25F H 0.4785 0.3711 0.1672 0.061 Uiso 1 1 calc GR . . . .


_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
C1 C2 1.403(7) . ?
C1 C6 1.381(7) . ?
C1 C7 1.420(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.365(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.411(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.362(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.406(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.201(7) . ?
C8 C9 1.451(7) . ?
C9 C10 1.398(6) . ?
C9 C14 1.391(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.376(6) . ?
C11 C12 1.425(6) . ?
C11 C16 1.487(6) 2_766 ?
C12 C13 1.381(6) . ?
C12 C15 1.461(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.397(6) . ?
C14 H14 0.9500 . ?
C15 C15 1.460(8) 2_766 ?
C15 C16 1.360(6) . ?
C16 C11 1.487(6) 2_766 ?
C16 C17 1.487(6) . ?
C17 C18 1.408(6) . ?
C17 C22 1.404(6) . ?
C18 C19 1.391(6) . ?
C18 C23 1.510(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.397(6) . ?
C20 C21 1.393(7) . ?
C20 C24 1.509(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(6) . ?
C22 C25 1.499(6) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C1' C2' 1.390(7) . ?
C1' C6' 1.381(7) . ?
C1' C7' 1.445(6) . ?
C2' H2' 0.9500 . ?
C2' C3' 1.404(7) . ?
C3' H3' 0.9500 . ?
C3' C4' 1.346(7) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.381(7) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.393(7) . ?
C6' H6' 0.9500 . ?
C7' C8' 1.194(6) . ?
C8' C9' 1.445(6) . ?
C9' C10' 1.406(6) . ?
C9' C14' 1.401(6) . ?
C10' H10' 0.9500 . ?
C10' C11' 1.384(6) . ?
C11' C12' 1.431(6) . ?
C11' C16' 1.477(6) 2_665 ?
C12' C13' 1.377(6) . ?
C12' C15' 1.468(6) . ?
C13' H13' 0.9500 . ?
C13' C14' 1.387(6) . ?
C14' H14' 0.9500 . ?
C15' C15' 1.464(8) 2_665 ?
C15' C16' 1.362(6) . ?
C16' C11' 1.477(6) 2_665 ?
C16' C17' 1.481(6) . ?
C17' C18' 1.400(6) . ?
C17' C22' 1.404(6) . ?
C18' C19' 1.387(6) . ?
C18' C23' 1.499(7) . ?
C19' H19' 0.9500 . ?
C19' C20' 1.391(7) . ?
C20' C21' 1.402(7) . ?
C20' C24' 1.489(6) . ?
C21' H21' 0.9500 . ?
C21' C22' 1.384(6) . ?
C22' C25' 1.510(7) . ?
C23' H23D 0.9800 . ?
C23' H23E 0.9800 . ?
C23' H23F 0.9800 . ?
C24' H24D 0.9800 . ?
C24' H24E 0.9800 . ?
C24' H24F 0.9800 . ?
C25' H25D 0.9800 . ?
C25' H25E 0.9800 . ?
C25' H25F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C7 119.3(5) . . ?
C6 C1 C2 119.1(5) . . ?
C6 C1 C7 121.5(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.5(5) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.1(5) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.9(5) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(5) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 120.4(5) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C1 177.1(5) . . ?
C7 C8 C9 171.8(5) . . ?
C10 C9 C8 118.5(4) . . ?
C14 C9 C8 121.3(4) . . ?
C14 C9 C10 120.2(4) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.2(4) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C12 120.8(4) . . ?
C10 C11 C16 130.0(4) . 2_766 ?
C12 C11 C16 109.2(4) . 2_766 ?
C11 C12 C15 106.2(4) . . ?
C13 C12 C11 119.4(4) . . ?
C13 C12 C15 134.4(4) . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.5(4) . . ?
C14 C13 H13 120.2 . . ?
C9 C14 C13 120.8(4) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C15 C15 C12 107.1(4) 2_766 . ?
C16 C15 C12 142.2(4) . . ?
C16 C15 C15 110.7(5) . 2_766 ?
C11 C16 C17 124.1(4) 2_766 . ?
C15 C16 C11 106.8(4) . 2_766 ?
C15 C16 C17 129.0(4) . . ?
C18 C17 C16 119.8(4) . . ?
C22 C17 C16 119.8(4) . . ?
C22 C17 C18 120.4(4) . . ?
C17 C18 C23 121.9(4) . . ?
C19 C18 C17 118.9(4) . . ?
C19 C18 C23 119.2(4) . . ?
C18 C19 H19 119.2 . . ?
C18 C19 C20 121.5(4) . . ?
C20 C19 H19 119.2 . . ?
C19 C20 C24 121.3(4) . . ?
C21 C20 C19 118.3(4) . . ?
C21 C20 C24 120.4(4) . . ?
C20 C21 H21 119.0 . . ?
C22 C21 C20 122.1(4) . . ?
C22 C21 H21 119.0 . . ?
C17 C22 C25 122.1(4) . . ?
C21 C22 C17 118.8(4) . . ?
C21 C22 C25 119.1(4) . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C2' C1' C7' 119.6(4) . . ?
C6' C1' C2' 120.3(4) . . ?
C6' C1' C7' 120.1(4) . . ?
C1' C2' H2' 120.4 . . ?
C1' C2' C3' 119.3(5) . . ?
C3' C2' H2' 120.4 . . ?
C2' C3' H3' 119.9 . . ?
C4' C3' C2' 120.1(5) . . ?
C4' C3' H3' 119.9 . . ?
C3' C4' H4' 119.5 . . ?
C3' C4' C5' 121.0(5) . . ?
C5' C4' H4' 119.5 . . ?
C4' C5' H5' 120.0 . . ?
C4' C5' C6' 120.0(5) . . ?
C6' C5' H5' 120.0 . . ?
C1' C6' C5' 119.3(4) . . ?
C1' C6' H6' 120.4 . . ?
C5' C6' H6' 120.4 . . ?
C8' C7' C1' 178.9(5) . . ?
C7' C8' C9' 177.8(5) . . ?
C10' C9' C8' 118.7(4) . . ?
C14' C9' C8' 120.8(4) . . ?
C14' C9' C10' 120.5(4) . . ?
C9' C10' H10' 120.5 . . ?
C11' C10' C9' 118.9(4) . . ?
C11' C10' H10' 120.5 . . ?
C10' C11' C12' 119.7(4) . . ?
C10' C11' C16' 129.8(4) . 2_665 ?
C12' C11' C16' 110.4(3) . 2_665 ?
C11' C12' C15' 104.9(4) . . ?
C13' C12' C11' 121.0(4) . . ?
C13' C12' C15' 134.1(4) . . ?
C12' C13' H13' 120.5 . . ?
C12' C13' C14' 119.0(4) . . ?
C14' C13' H13' 120.5 . . ?
C9' C14' H14' 119.6 . . ?
C13' C14' C9' 120.9(4) . . ?
C13' C14' H14' 119.6 . . ?
C15' C15' C12' 107.6(4) 2_665 . ?
C16' C15' C12' 141.8(4) . . ?
C16' C15' C15' 110.6(4) . 2_665 ?
C11' C16' C17' 125.8(4) 2_665 . ?
C15' C16' C11' 106.6(4) . 2_665 ?
C15' C16' C17' 127.6(4) . . ?
C18' C17' C16' 119.3(4) . . ?
C18' C17' C22' 121.2(4) . . ?
C22' C17' C16' 119.5(4) . . ?
C17' C18' C23' 121.7(4) . . ?
C19' C18' C17' 118.3(4) . . ?
C19' C18' C23' 120.0(4) . . ?
C18' C19' H19' 118.7 . . ?
C18' C19' C20' 122.5(4) . . ?
C20' C19' H19' 118.7 . . ?
C19' C20' C21' 117.2(4) . . ?
C19' C20' C24' 120.9(5) . . ?
C21' C20' C24' 121.8(5) . . ?
C20' C21' H21' 118.7 . . ?
C22' C21' C20' 122.6(4) . . ?
C22' C21' H21' 118.7 . . ?
C17' C22' C25' 120.9(4) . . ?
C21' C22' C17' 118.0(4) . . ?
C21' C22' C25' 121.1(4) . . ?
C18' C23' H23D 109.5 . . ?
C18' C23' H23E 109.5 . . ?
C18' C23' H23F 109.5 . . ?
H23D C23' H23E 109.5 . . ?
H23D C23' H23F 109.5 . . ?
H23E C23' H23F 109.5 . . ?
C20' C24' H24D 109.5 . . ?
C20' C24' H24E 109.5 . . ?
C20' C24' H24F 109.5 . . ?
H24D C24' H24E 109.5 . . ?
H24D C24' H24F 109.5 . . ?
H24E C24' H24F 109.5 . . ?
C22' C25' H25D 109.5 . . ?
C22' C25' H25E 109.5 . . ?
C22' C25' H25F 109.5 . . ?
H25D C25' H25E 109.5 . . ?
H25D C25' H25F 109.5 . . ?
H25E C25' H25F 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
C1 C2 C3 C4 -0.3(7) . . . . ?
C2 C1 C6 C5 -1.5(7) . . . . ?
C2 C3 C4 C5 1.2(8) . . . . ?
C3 C4 C5 C6 -2.3(8) . . . . ?
C4 C5 C6 C1 2.4(7) . . . . ?
C6 C1 C2 C3 0.5(7) . . . . ?
C7 C1 C2 C3 179.4(4) . . . . ?
C7 C1 C6 C5 179.6(4) . . . . ?
C8 C9 C10 C11 178.2(4) . . . . ?
C8 C9 C14 C13 -177.3(4) . . . . ?
C9 C10 C11 C12 -1.3(6) . . . . ?
C9 C10 C11 C16 179.8(4) . . . 2_766 ?
C10 C9 C14 C13 0.2(6) . . . . ?
C10 C11 C12 C13 1.1(6) . . . . ?
C10 C11 C12 C15 -178.4(4) . . . . ?
C11 C12 C13 C14 -0.3(6) . . . . ?
C11 C12 C15 C15 -0.2(5) . . . 2_766 ?
C11 C12 C15 C16 179.2(5) . . . . ?
C11 C16 C17 C18 -108.9(5) 2_766 . . . ?
C11 C16 C17 C22 69.2(6) 2_766 . . . ?
C12 C13 C14 C9 -0.4(6) . . . . ?
C12 C15 C16 C11 179.8(5) . . . 2_766 ?
C12 C15 C16 C17 0.1(9) . . . . ?
C13 C12 C15 C15 -179.6(5) . . . 2_766 ?
C13 C12 C15 C16 -0.3(10) . . . . ?
C14 C9 C10 C11 0.6(6) . . . . ?
C15 C12 C13 C14 179.1(4) . . . . ?
C15 C15 C16 C11 -0.8(6) 2_766 . . 2_766 ?
C15 C15 C16 C17 179.4(4) 2_766 . . . ?
C15 C16 C17 C18 70.8(6) . . . . ?
C15 C16 C17 C22 -111.0(5) . . . . ?
C16 C11 C12 C13 -179.8(4) 2_766 . . . ?
C16 C11 C12 C15 0.7(4) 2_766 . . . ?
C16 C17 C18 C19 179.3(4) . . . . ?
C16 C17 C18 C23 -0.3(7) . . . . ?
C16 C17 C22 C21 -178.5(4) . . . . ?
C16 C17 C22 C25 2.8(7) . . . . ?
C17 C18 C19 C20 -0.6(7) . . . . ?
C18 C17 C22 C21 -0.4(7) . . . . ?
C18 C17 C22 C25 -179.1(4) . . . . ?
C18 C19 C20 C21 -0.7(7) . . . . ?
C18 C19 C20 C24 -179.7(5) . . . . ?
C19 C20 C21 C22 1.5(7) . . . . ?
C20 C21 C22 C17 -0.9(7) . . . . ?
C20 C21 C22 C25 177.8(4) . . . . ?
C22 C17 C18 C19 1.2(7) . . . . ?
C22 C17 C18 C23 -178.4(4) . . . . ?
C23 C18 C19 C20 179.0(5) . . . . ?
C24 C20 C21 C22 -179.5(5) . . . . ?
C1' C2' C3' C4' 0.1(9) . . . . ?
C2' C1' C6' C5' 0.1(7) . . . . ?
C2' C3' C4' C5' -0.3(9) . . . . ?
C3' C4' C5' C6' 0.5(8) . . . . ?
C4' C5' C6' C1' -0.4(7) . . . . ?
C6' C1' C2' C3' 0.1(8) . . . . ?
C7' C1' C2' C3' -178.8(5) . . . . ?
C7' C1' C6' C5' 179.0(4) . . . . ?
C8' C9' C10' C11' 179.9(4) . . . . ?
C8' C9' C14' C13' 179.9(4) . . . . ?
C9' C10' C11' C12' 1.0(6) . . . . ?
C9' C10' C11' C16' 178.7(4) . . . 2_665 ?
C10' C9' C14' C13' 1.2(7) . . . . ?
C10' C11' C12' C13' -0.3(6) . . . . ?
C10' C11' C12' C15' 177.5(4) . . . . ?
C11' C12' C13' C14' 0.1(7) . . . . ?
C11' C12' C15' C15' -0.3(6) . . . 2_665 ?
C11' C12' C15' C16' -178.5(6) . . . . ?
C11' C16' C17' C18' -70.8(6) 2_665 . . . ?
C11' C16' C17' C22' 109.8(5) 2_665 . . . ?
C12' C13' C14' C9' -0.5(7) . . . . ?
C12' C15' C16' C11' 179.7(6) . . . 2_665 ?
C12' C15' C16' C17' -1.3(9) . . . . ?
C13' C12' C15' C15' 177.1(5) . . . 2_665 ?
C13' C12' C15' C16' -1.1(10) . . . . ?
C14' C9' C10' C11' -1.4(7) . . . . ?
C15' C12' C13' C14' -177.0(5) . . . . ?
C15' C15' C16' C11' 1.5(6) 2_665 . . 2_665 ?
C15' C15' C16' C17' -179.5(5) 2_665 . . . ?
C15' C16' C17' C18' 110.4(5) . . . . ?
C15' C16' C17' C22' -69.0(6) . . . . ?
C16' C11' C12' C13' -178.5(4) 2_665 . . . ?
C16' C11' C12' C15' -0.6(5) 2_665 . . . ?
C16' C17' C18' C19' -177.1(4) . . . . ?
C16' C17' C18' C23' 2.1(6) . . . . ?
C16' C17' C22' C21' 175.6(4) . . . . ?
C16' C17' C22' C25' -5.1(6) . . . . ?
C17' C18' C19' C20' 1.0(7) . . . . ?
C18' C17' C22' C21' -3.7(6) . . . . ?
C18' C17' C22' C25' 175.5(4) . . . . ?
C18' C19' C20' C21' -2.5(7) . . . . ?
C18' C19' C20' C24' 179.3(4) . . . . ?
C19' C20' C21' C22' 0.9(7) . . . . ?
C20' C21' C22' C17' 2.1(7) . . . . ?
C20' C21' C22' C25' -177.1(4) . . . . ?
C22' C17' C18' C19' 2.2(6) . . . . ?
C22' C17' C18' C23' -178.5(4) . . . . ?
C23' C18' C19' C20' -178.3(4) . . . . ?
C24' C20' C21' C22' 179.1(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 0.000 0.500 168.3 61.2 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
#END---------------------------------------------------------------------------
