# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_256rmb15
_database_code_depnum_ccdc_archive 'CCDC 1477344'
_audit_update_record             
;
2016-04-29 deposited with the CCDC.
2016-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H16 Br4 N2'
_chemical_formula_sum            'C30 H16 Br4 N2'
_chemical_formula_weight         724.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 2/c'
_space_group_name_Hall           '-C 2yc'

_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. 
;

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

_cell_length_a                   28.8213(16)
_cell_length_b                   3.9568(2)
_cell_length_c                   22.0852(14)
_cell_angle_alpha                90
_cell_angle_beta                 101.200(3)
_cell_angle_gamma                90
_cell_volume                     2470.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4709
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      25.55

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.947
_exptl_crystal_F_000             1400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    6.540
_shelx_estimated_absorpt_T_min   0.355
_shelx_estimated_absorpt_T_max   0.780
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6582
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'sadabs, Sheldrick, G. M. (1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0.83
_diffrn_reflns_number            8974
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.581
_diffrn_reflns_theta_max         25.673
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2308
_reflns_number_gt                1564
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 V2014 (Bruker, 2012)'
_computing_cell_refinement       'APEX2 V2014 (Bruker, 2012)'
_computing_data_reduction        'SAINT V 827A (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0369P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2308
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0774
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.85592(2) 0.27445(16) 0.37275(3) 0.0576(2) Uani 1 1 d . . . . .
Br2 Br 1.02582(2) -0.37779(14) 0.11079(3) 0.0544(2) Uani 1 1 d . . . . .
C1 C 0.79451(14) 0.3575(11) 0.1879(2) 0.0344(12) Uani 1 1 d . . . . .
H1 H 0.7659 0.4345 0.1650 0.041 Uiso 1 1 calc R U . . .
C2 C 0.80370(14) 0.3733(11) 0.2513(2) 0.0358(12) Uani 1 1 d . . . . .
H2 H 0.7813 0.4643 0.2718 0.043 Uiso 1 1 calc R U . . .
C3 C 0.84652(15) 0.2534(11) 0.2852(2) 0.0337(11) Uani 1 1 d . . . . .
C4 C 0.88124(14) 0.1264(10) 0.2577(2) 0.0335(11) Uani 1 1 d . . . . .
H4 H 0.9097 0.0516 0.2811 0.040 Uiso 1 1 calc R U . . .
C4A C 0.87272(13) 0.1120(10) 0.1932(2) 0.0291(10) Uani 1 1 d . . . . .
C4B C 0.90121(13) 0.0034(11) 0.1498(2) 0.0308(11) Uani 1 1 d . . . . .
C5 C 0.94641(14) -0.1290(11) 0.1555(2) 0.0383(12) Uani 1 1 d . . . . .
H5 H 0.9649 -0.1681 0.1943 0.046 Uiso 1 1 calc R U . . .
C6 C 0.96351(15) -0.2015(11) 0.1032(3) 0.0394(12) Uani 1 1 d . . . . .
C7 C 0.93681(15) -0.1484(12) 0.0449(2) 0.0427(13) Uani 1 1 d . . . . .
H7 H 0.9494 -0.2006 0.0103 0.051 Uiso 1 1 calc R U . . .
C8 C 0.89134(15) -0.0177(12) 0.0377(2) 0.0413(12) Uani 1 1 d . . . . .
H8 H 0.8732 0.0189 -0.0015 0.050 Uiso 1 1 calc R U . . .
C8A C 0.87375(14) 0.0568(11) 0.0901(2) 0.0302(11) Uani 1 1 d . . . . .
N9 N 0.82960(11) 0.1864(9) 0.09627(17) 0.0328(9) Uani 1 1 d . . . . .
C9A C 0.82919(13) 0.2230(10) 0.1590(2) 0.0271(10) Uani 1 1 d . . . . .
C10 C 0.78927(13) 0.2179(11) 0.0474(2) 0.0308(11) Uani 1 1 d . . . . .
C11 C 0.79300(14) 0.3826(11) -0.0064(2) 0.0328(11) Uani 1 1 d . . . . .
H11 H 0.8218 0.4747 -0.0108 0.039 Uiso 1 1 calc R U . . .
C12 C 0.75411(14) 0.4118(11) -0.0539(2) 0.0348(11) Uani 1 1 d . . . . .
H12 H 0.7571 0.5191 -0.0904 0.042 Uiso 1 1 calc R 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
Br1 C3 1.901(4) . ?
Br1 Br2 3.6278(8) 2_765 ?
Br2 C6 1.903(4) . ?
C1 C2 1.375(6) . ?
C1 C9A 1.392(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.396(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(6) . ?
C4 C4A 1.398(6) . ?
C4 H4 0.9300 . ?
C4A C9A 1.403(5) . ?
C4A C4B 1.444(6) . ?
C4B C5 1.387(6) . ?
C4B C8A 1.415(6) . ?
C5 C6 1.372(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(7) . ?
C7 C8 1.389(6) . ?
C7 H7 0.9300 . ?
C8 C8A 1.383(6) . ?
C8 H8 0.9300 . ?
C8A N9 1.403(5) . ?
N9 C9A 1.395(6) . ?
N9 C10 1.429(5) . ?
C10 C11 1.378(6) . ?
C10 C12 1.385(6) 7_655 ?
C11 C12 1.384(6) . ?
C11 H11 0.9300 . ?
C12 C10 1.384(6) 7_655 ?
C12 H12 0.9300 . ?

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 Br1 Br2 93.68(13) . 2_765 ?
C2 C1 C9A 118.1(4) . . ?
C2 C1 H1 120.9 . . ?
C9A C1 H1 120.9 . . ?
C1 C2 C3 120.4(4) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 122.3(4) . . ?
C4 C3 Br1 119.9(3) . . ?
C2 C3 Br1 117.8(3) . . ?
C3 C4 C4A 118.1(4) . . ?
C3 C4 H4 121.0 . . ?
C4A C4 H4 121.0 . . ?
C4 C4A C9A 119.8(4) . . ?
C4 C4A C4B 132.7(4) . . ?
C9A C4A C4B 107.4(4) . . ?
C5 C4B C8A 119.2(4) . . ?
C5 C4B C4A 134.2(4) . . ?
C8A C4B C4A 106.7(3) . . ?
C6 C5 C4B 119.1(4) . . ?
C6 C5 H5 120.4 . . ?
C4B C5 H5 120.4 . . ?
C5 C6 C7 121.8(4) . . ?
C5 C6 Br2 119.3(4) . . ?
C7 C6 Br2 118.9(4) . . ?
C6 C7 C8 120.5(5) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C8A C8 C7 118.3(4) . . ?
C8A C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C8 C8A N9 130.2(4) . . ?
C8 C8A C4B 121.2(4) . . ?
N9 C8A C4B 108.5(4) . . ?
C9A N9 C8A 108.5(3) . . ?
C9A N9 C10 125.3(3) . . ?
C8A N9 C10 125.3(4) . . ?
C1 C9A N9 129.8(4) . . ?
C1 C9A C4A 121.2(4) . . ?
N9 C9A C4A 108.9(4) . . ?
C11 C10 C12 119.2(4) . 7_655 ?
C11 C10 N9 120.3(4) . . ?
C12 C10 N9 120.5(4) 7_655 . ?
C10 C11 C12 120.4(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C10 120.3(4) . 7_655 ?
C11 C12 H12 119.8 . . ?
C10 C12 H12 119.8 7_655 . ?

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
C9A C1 C2 C3 -0.7(7) . . . . ?
C1 C2 C3 C4 1.9(7) . . . . ?
C1 C2 C3 Br1 -178.6(3) . . . . ?
C2 C3 C4 C4A -1.2(6) . . . . ?
Br1 C3 C4 C4A 179.3(3) . . . . ?
C3 C4 C4A C9A -0.7(6) . . . . ?
C3 C4 C4A C4B 178.2(4) . . . . ?
C4 C4A C4B C5 1.1(8) . . . . ?
C9A C4A C4B C5 -179.8(5) . . . . ?
C4 C4A C4B C8A -178.4(4) . . . . ?
C9A C4A C4B C8A 0.6(5) . . . . ?
C8A C4B C5 C6 0.7(7) . . . . ?
C4A C4B C5 C6 -178.8(5) . . . . ?
C4B C5 C6 C7 -0.5(7) . . . . ?
C4B C5 C6 Br2 179.2(3) . . . . ?
C5 C6 C7 C8 0.1(7) . . . . ?
Br2 C6 C7 C8 -179.5(3) . . . . ?
C6 C7 C8 C8A -0.1(7) . . . . ?
C7 C8 C8A N9 -179.4(4) . . . . ?
C7 C8 C8A C4B 0.3(7) . . . . ?
C5 C4B C8A C8 -0.6(7) . . . . ?
C4A C4B C8A C8 179.0(4) . . . . ?
C5 C4B C8A N9 179.2(4) . . . . ?
C4A C4B C8A N9 -1.2(5) . . . . ?
C8 C8A N9 C9A -178.9(5) . . . . ?
C4B C8A N9 C9A 1.4(5) . . . . ?
C8 C8A N9 C10 11.3(7) . . . . ?
C4B C8A N9 C10 -168.4(4) . . . . ?
C2 C1 C9A N9 -178.1(4) . . . . ?
C2 C1 C9A C4A -1.2(6) . . . . ?
C8A N9 C9A C1 176.2(4) . . . . ?
C10 N9 C9A C1 -14.0(7) . . . . ?
C8A N9 C9A C4A -1.0(5) . . . . ?
C10 N9 C9A C4A 168.8(4) . . . . ?
C4 C4A C9A C1 1.9(6) . . . . ?
C4B C4A C9A C1 -177.3(4) . . . . ?
C4 C4A C9A N9 179.4(4) . . . . ?
C4B C4A C9A N9 0.2(5) . . . . ?
C9A N9 C10 C11 139.2(4) . . . . ?
C8A N9 C10 C11 -52.7(6) . . . . ?
C9A N9 C10 C12 -39.8(6) . . . 7_655 ?
C8A N9 C10 C12 128.3(5) . . . 7_655 ?
C12 C10 C11 C12 -1.4(7) 7_655 . . . ?
N9 C10 C11 C12 179.6(4) . . . . ?
C10 C11 C12 C10 1.4(7) . . . 7_655 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 Br1 0.93 2.96 3.727(5) 140.5 6
C11 H11 Br1 0.93 3.09 3.760(5) 130.4 6_565

_refine_diff_density_max         0.560
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.098

_shelxl_version_number           2013-2



####################################################################### 
# 
# 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_041rmb16
_database_code_depnum_ccdc_archive 'CCDC 1477345'
_audit_update_record             
;
2016-04-29 deposited with the CCDC.
2016-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H16 Br4 N2'
_chemical_formula_sum            'C30 H16 Br4 N2'
_chemical_formula_weight         724.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 2/c'
_space_group_name_Hall           '-C 2yc'

_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. 
;

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

_cell_length_a                   28.561(3)
_cell_length_b                   3.8983(4)
_cell_length_c                   22.009(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.956(2)
_cell_angle_gamma                90
_cell_volume                     2405.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3628
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      25.07

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.999
_exptl_crystal_F_000             1400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    6.716
_shelx_estimated_absorpt_T_min   0.220
_shelx_estimated_absorpt_T_max   0.705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3937
_exptl_absorpt_correction_T_max  0.7936
_exptl_absorpt_process_details   'SHELXTL (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   fine-focus
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0.83
_diffrn_reflns_number            4866
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_av_R_equivalents  0.0905
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.150
_diffrn_reflns_theta_max         25.076
_diffrn_reflns_theta_full        25.076
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2141
_reflns_number_gt                1741
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 V2012 (Bruker, 2012)'
_computing_cell_refinement       'APEX2 V2012 (Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B  (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'SHELXTL  (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0239P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2141
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0641
_refine_ls_wR_factor_gt          0.0596
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.85553(2) 0.26258(11) 0.37314(2) 0.02885(13) Uani 1 1 d . . . . .
Br2 Br 1.02756(2) -0.38396(10) 0.11014(2) 0.02564(13) Uani 1 1 d . . . . .
C1 C 0.79434(12) 0.3572(9) 0.18819(16) 0.0166(8) Uani 1 1 d . . . . .
H1 H 0.7650 0.4378 0.1649 0.020 Uiso 1 1 calc R U . . .
C2 C 0.80391(12) 0.3697(9) 0.25196(16) 0.0169(8) Uani 1 1 d . . . . .
H2 H 0.7808 0.4635 0.2731 0.020 Uiso 1 1 calc R U . . .
C3 C 0.84641(12) 0.2485(9) 0.28551(15) 0.0159(8) Uani 1 1 d . . . . .
C4 C 0.88203(12) 0.1200(9) 0.25789(15) 0.0150(8) Uani 1 1 d . . . . .
H4 H 0.9114 0.0425 0.2816 0.018 Uiso 1 1 calc R U . . .
C4A C 0.87297(12) 0.1087(9) 0.19346(15) 0.0139(7) Uani 1 1 d . . . . .
C4B C 0.90209(11) 0.0023(9) 0.14942(15) 0.0140(7) Uani 1 1 d . . . . .
C5 C 0.94773(12) -0.1328(9) 0.15572(16) 0.0186(8) Uani 1 1 d . . . . .
H5 H 0.9666 -0.1738 0.1955 0.022 Uiso 1 1 calc R U . . .
C6 C 0.96493(12) -0.2056(9) 0.10298(17) 0.0192(8) Uani 1 1 d . . . . .
C7 C 0.93796(13) -0.1455(9) 0.04409(17) 0.0202(8) Uani 1 1 d . . . . .
H7 H 0.9511 -0.1959 0.0085 0.024 Uiso 1 1 calc R U . . .
C8 C 0.89267(12) -0.0142(9) 0.03716(16) 0.0196(8) Uani 1 1 d . . . . .
H8 H 0.8741 0.0262 -0.0028 0.023 Uiso 1 1 calc R U . . .
C8A C 0.87463(12) 0.0582(9) 0.09001(15) 0.0151(8) Uani 1 1 d . . . . .
N9 N 0.82995(10) 0.1885(7) 0.09600(13) 0.0162(7) Uani 1 1 d . . . . .
C9A C 0.82981(12) 0.2206(8) 0.15921(16) 0.0149(8) Uani 1 1 d . . . . .
C10 C 0.78947(12) 0.2217(9) 0.04780(16) 0.0163(8) Uani 1 1 d . . . . .
C11 C 0.79323(12) 0.3872(9) -0.00703(15) 0.0160(8) Uani 1 1 d . . . . .
H11 H 0.8229 0.4830 -0.0118 0.019 Uiso 1 1 calc R U . . .
C12 C 0.75426(12) 0.4132(9) -0.05439(15) 0.0153(8) Uani 1 1 d . . . . .
H12 H 0.7573 0.5243 -0.0919 0.018 Uiso 1 1 calc R 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
Br1 C3 1.897(3) . ?
Br2 C6 1.898(3) . ?
C1 C2 1.379(5) . ?
C1 C9A 1.401(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(4) . ?
C4 C4A 1.393(5) . ?
C4 H4 0.9500 . ?
C4A C9A 1.387(5) . ?
C4A C4B 1.452(4) . ?
C4B C5 1.388(5) . ?
C4B C8A 1.408(5) . ?
C5 C6 1.373(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.396(5) . ?
C7 C8 1.372(5) . ?
C7 H7 0.9500 . ?
C8 C8A 1.388(4) . ?
C8 H8 0.9500 . ?
C8A N9 1.403(4) . ?
N9 C9A 1.398(4) . ?
N9 C10 1.419(4) . ?
C10 C12 1.388(5) 7_655 ?
C10 C11 1.390(5) . ?
C11 C12 1.376(5) . ?
C11 H11 0.9500 . ?
C12 C10 1.388(5) 7_655 ?
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
C2 C1 C9A 117.2(3) . . ?
C2 C1 H1 121.4 . . ?
C9A C1 H1 121.4 . . ?
C3 C2 C1 121.1(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 122.6(3) . . ?
C4 C3 Br1 119.3(3) . . ?
C2 C3 Br1 118.1(2) . . ?
C3 C4 C4A 116.9(3) . . ?
C3 C4 H4 121.6 . . ?
C4A C4 H4 121.6 . . ?
C9A C4A C4 121.1(3) . . ?
C9A C4A C4B 106.8(3) . . ?
C4 C4A C4B 132.0(3) . . ?
C5 C4B C8A 119.9(3) . . ?
C5 C4B C4A 133.4(3) . . ?
C8A C4B C4A 106.7(3) . . ?
C6 C5 C4B 118.3(3) . . ?
C6 C5 H5 120.9 . . ?
C4B C5 H5 120.9 . . ?
C5 C6 C7 121.8(3) . . ?
C5 C6 Br2 119.2(3) . . ?
C7 C6 Br2 118.9(3) . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C8A 118.4(3) . . ?
C7 C8 H8 120.8 . . ?
C8A C8 H8 120.8 . . ?
C8 C8A N9 129.9(3) . . ?
C8 C8A C4B 121.1(3) . . ?
N9 C8A C4B 109.0(3) . . ?
C9A N9 C8A 107.5(3) . . ?
C9A N9 C10 125.5(3) . . ?
C8A N9 C10 126.1(3) . . ?
C4A C9A N9 110.0(3) . . ?
C4A C9A C1 121.1(3) . . ?
N9 C9A C1 128.8(3) . . ?
C12 C10 C11 119.1(3) 7_655 . ?
C12 C10 N9 120.6(3) 7_655 . ?
C11 C10 N9 120.3(3) . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C10 120.5(3) . 7_655 ?
C11 C12 H12 119.8 . . ?
C10 C12 H12 119.8 7_655 . ?

_refine_diff_density_max         0.596
_refine_diff_density_min         -1.109
_refine_diff_density_rms         0.153



####################################################################### 
# 
# 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_221RMB16
_database_code_depnum_ccdc_archive 'CCDC 1480582'
_audit_update_record             
;
2016-05-18 deposited with the CCDC.
2016-09-26 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H16 Br4 N2'
_chemical_formula_sum            'C30 H16 Br4 N2'
_chemical_formula_weight         724.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 2/c'
_space_group_name_Hall           '-C 2yc'

_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. 
;

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

_cell_length_a                   28.6436(14)
_cell_length_b                   3.9085(2)
_cell_length_c                   22.0408(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.0626(14)
_cell_angle_gamma                90
_cell_volume                     2421.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      25.30

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.986
_exptl_crystal_F_000             1400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    6.672
_shelx_estimated_absorpt_T_min   0.221
_shelx_estimated_absorpt_T_max   0.706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6195
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS-2014/5 - Bruker AXS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ-geometry diffractometer 208039-01'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            15906
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.587
_diffrn_reflns_theta_max         25.318
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2208
_reflns_number_gt                1672
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX3 v2016.1 (Bruker, 2014)'
_computing_cell_refinement       'APEX3 v2016.1 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.37A  (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2014 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²+36.7816P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2208
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0926
_refine_ls_goodness_of_fit_ref   1.252
_refine_ls_restrained_S_all      1.252
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.85557(2) 0.2650(2) 0.37298(3) 0.0363(2) Uani 1 1 d . . . . .
Br2 Br 1.02719(2) -0.3832(2) 0.11030(3) 0.0320(2) Uani 1 1 d . . . . .
C1 C 0.7943(2) 0.3568(17) 0.1879(3) 0.0197(15) Uani 1 1 d . . . . .
H1 H 0.7649 0.4362 0.1645 0.024 Uiso 1 1 calc R U . . .
C2 C 0.8035(2) 0.3702(17) 0.2519(3) 0.0198(15) Uani 1 1 d . . . . .
H2 H 0.7804 0.4622 0.2729 0.024 Uiso 1 1 calc R U . . .
C3 C 0.8464(2) 0.2503(18) 0.2856(3) 0.0213(15) Uani 1 1 d . . . . .
C4 C 0.8818(2) 0.1231(18) 0.2576(3) 0.0204(15) Uani 1 1 d . . . . .
H4 H 0.9112 0.0475 0.2813 0.024 Uiso 1 1 calc R U . . .
C4A C 0.8729(2) 0.1088(17) 0.1935(3) 0.0156(14) Uani 1 1 d . . . . .
C4B C 0.90187(19) 0.0025(17) 0.1497(3) 0.0165(14) Uani 1 1 d . . . . .
C5 C 0.9474(2) -0.1332(18) 0.1559(3) 0.0234(16) Uani 1 1 d . . . . .
H5 H 0.9662 -0.1742 0.1956 0.028 Uiso 1 1 calc R U . . .
C6 C 0.9646(2) -0.2074(18) 0.1029(3) 0.0240(16) Uani 1 1 d . . . . .
C7 C 0.9376(2) -0.1498(18) 0.0446(3) 0.0256(16) Uani 1 1 d . . . . .
H7 H 0.9504 -0.2038 0.0091 0.031 Uiso 1 1 calc R U . . .
C8 C 0.8923(2) -0.0153(19) 0.0374(3) 0.0255(16) Uani 1 1 d . . . . .
H8 H 0.8739 0.0269 -0.0026 0.031 Uiso 1 1 calc R U . . .
C8A C 0.8745(2) 0.0562(17) 0.0902(3) 0.0169(14) Uani 1 1 d . . . . .
N9 N 0.83009(16) 0.1864(15) 0.0962(2) 0.0203(13) Uani 1 1 d . . . . .
C9A C 0.8294(2) 0.2234(18) 0.1591(3) 0.0184(14) Uani 1 1 d . . . . .
C10 C 0.7896(2) 0.2243(18) 0.0478(3) 0.0193(15) Uani 1 1 d . . . . .
C11 C 0.7932(2) 0.3852(18) -0.0070(3) 0.0209(15) Uani 1 1 d . . . . .
H11 H 0.8229 0.4762 -0.0123 0.025 Uiso 1 1 calc R U . . .
C12 C 0.7538(2) 0.4142(19) -0.0542(3) 0.0221(15) Uani 1 1 d . . . . .
H12 H 0.7565 0.5299 -0.0913 0.026 Uiso 1 1 calc R 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
Br1 C3 1.894(6) . ?
Br2 C6 1.896(6) . ?
C1 C2 1.385(8) . ?
C1 C9A 1.388(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(8) . ?
C4 C4A 1.387(8) . ?
C4 H4 0.9500 . ?
C4A C9A 1.403(8) . ?
C4A C4B 1.449(8) . ?
C4B C5 1.390(8) . ?
C4B C8A 1.409(8) . ?
C5 C6 1.383(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(9) . ?
C7 C8 1.379(9) . ?
C7 H7 0.9500 . ?
C8 C8A 1.386(8) . ?
C8 H8 0.9500 . ?
C8A N9 1.401(7) . ?
N9 C9A 1.398(7) . ?
N9 C10 1.424(7) . ?
C10 C11 1.384(9) . ?
C10 C12 1.387(8) 7_655 ?
C11 C12 1.385(8) . ?
C11 H11 0.9500 . ?
C12 C10 1.388(8) 7_655 ?
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
C2 C1 C9A 117.8(5) . . ?
C2 C1 H1 121.1 . . ?
C9A C1 H1 121.1 . . ?
C1 C2 C3 120.6(5) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 122.2(6) . . ?
C4 C3 Br1 119.8(5) . . ?
C2 C3 Br1 118.0(4) . . ?
C3 C4 C4A 117.7(6) . . ?
C3 C4 H4 121.1 . . ?
C4A C4 H4 121.1 . . ?
C4 C4A C9A 120.5(5) . . ?
C4 C4A C4B 132.4(5) . . ?
C9A C4A C4B 107.1(5) . . ?
C5 C4B C8A 119.4(6) . . ?
C5 C4B C4A 133.7(5) . . ?
C8A C4B C4A 106.9(5) . . ?
C6 C5 C4B 118.5(6) . . ?
C6 C5 H5 120.7 . . ?
C4B C5 H5 120.7 . . ?
C5 C6 C7 121.4(6) . . ?
C5 C6 Br2 119.2(5) . . ?
C7 C6 Br2 119.3(5) . . ?
C8 C7 C6 121.0(6) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C8A 117.9(6) . . ?
C7 C8 H8 121.0 . . ?
C8A C8 H8 121.0 . . ?
C8 C8A N9 129.8(6) . . ?
C8 C8A C4B 121.6(6) . . ?
N9 C8A C4B 108.6(5) . . ?
C9A N9 C8A 108.6(5) . . ?
C9A N9 C10 124.5(5) . . ?
C8A N9 C10 126.3(5) . . ?
C1 C9A N9 129.9(5) . . ?
C1 C9A C4A 121.3(5) . . ?
N9 C9A C4A 108.8(5) . . ?
C11 C10 C12 119.0(5) . 7_655 ?
C11 C10 N9 120.9(5) . . ?
C12 C10 N9 120.0(6) 7_655 . ?
C10 C11 C12 120.4(6) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C10 120.6(6) . 7_655 ?
C11 C12 H12 119.7 . . ?
C10 C12 H12 119.7 7_655 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 Br1 0.95 2.92 3.704(6) 140.3 6
C11 H11 Br1 0.95 3.03 3.724(6) 130.9 6_565

_refine_diff_density_max         0.684
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.174




####################################################################### 
# 
# 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_224RMB16
_database_code_depnum_ccdc_archive 'CCDC 1480583'
_audit_update_record             
;
2016-05-18 deposited with the CCDC.
2016-09-26 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H16 Br4 N2'
_chemical_formula_weight         724.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 2/c'
_space_group_name_Hall           '-C 2yc'

_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. 
;

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

_cell_length_a                   28.6762(10)
_cell_length_b                   3.91570(10)
_cell_length_c                   22.0307(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.0789(11)
_cell_angle_gamma                90
_cell_volume                     2427.67(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    209(2)
_cell_measurement_reflns_used    9852
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      25.28

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.981
_exptl_crystal_F_000             1400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    6.656
_shelx_estimated_absorpt_T_min   0.210
_shelx_estimated_absorpt_T_max   0.825
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.5148
_exptl_absorpt_correction_T_max  0.8385
_exptl_absorpt_process_details   'SADABS-2014/5 - Bruker AXS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      209(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ-geometry diffractometer 208039-01'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            20268
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_av_R_equivalents  0.1038
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.587
_diffrn_reflns_theta_max         25.329
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2215
_reflns_number_gt                1743
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX3 v2016.1 (Bruker, 2014)'
_computing_cell_refinement       'APEX3 v2016.1 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.37A  (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2014 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0147P)²+29.8599P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2215
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 -0.14427(2) -0.26818(19) 0.37296(3) 0.0409(2) Uani 1 1 d . . . . .
Br2 Br 0.02686(2) 0.38130(17) 0.11038(3) 0.0365(2) Uani 1 1 d . . . . .
C1 C -0.20546(18) -0.3585(14) 0.1881(2) 0.0241(12) Uani 1 1 d . . . . .
H1 H -0.2344 -0.4392 0.1650 0.029 Uiso 1 1 calc R U . . .
C2 C -0.19640(17) -0.3707(15) 0.2516(2) 0.0245(12) Uani 1 1 d . . . . .
H2 H -0.2195 -0.4597 0.2724 0.029 Uiso 1 1 calc R U . . .
C3 C -0.15353(18) -0.2529(15) 0.2855(2) 0.0233(12) Uani 1 1 d . . . . .
C4 C -0.11821(17) -0.1221(15) 0.2576(2) 0.0221(12) Uani 1 1 d . . . . .
H4 H -0.0894 -0.0440 0.2813 0.027 Uiso 1 1 calc R U . . .
C4A C -0.12669(16) -0.1097(14) 0.1936(2) 0.0189(11) Uani 1 1 d . . . . .
C4B C -0.09813(16) -0.0030(14) 0.1498(2) 0.0193(11) Uani 1 1 d . . . . .
C5 C -0.05283(18) 0.1307(14) 0.1560(2) 0.0245(12) Uani 1 1 d . . . . .
H5 H -0.0342 0.1706 0.1953 0.029 Uiso 1 1 calc R U . . .
C6 C -0.03556(18) 0.2043(15) 0.1029(3) 0.0272(13) Uani 1 1 d . . . . .
C7 C -0.06254(18) 0.1478(15) 0.0445(2) 0.0272(13) Uani 1 1 d . . . . .
H7 H -0.0498 0.2004 0.0093 0.033 Uiso 1 1 calc R U . . .
C8 C -0.10785(18) 0.0156(15) 0.0372(2) 0.0239(12) Uani 1 1 d . . . . .
H8 H -0.1262 -0.0256 -0.0023 0.029 Uiso 1 1 calc R U . . .
C8A C -0.12551(17) -0.0548(14) 0.0905(2) 0.0214(12) Uani 1 1 d . . . . .
C9 C -0.17071(17) -0.2235(14) 0.1586(2) 0.0198(11) Uani 1 1 d . . . . .
N9 N -0.17012(14) -0.1880(12) 0.09615(18) 0.0225(10) Uani 1 1 d . . . . .
C10 C -0.21066(17) -0.2220(14) 0.0478(2) 0.0204(11) Uani 1 1 d . . . . .
C11 C -0.20701(17) -0.3861(15) -0.0072(2) 0.0249(12) Uani 1 1 d . . . . .
H11 H -0.1777 -0.4786 -0.0122 0.030 Uiso 1 1 calc R U . . .
C12 C -0.24605(17) -0.4133(14) -0.0542(2) 0.0219(12) Uani 1 1 d . . . . .
H12 H -0.2432 -0.5253 -0.0911 0.026 Uiso 1 1 calc R 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
Br1 C3 1.895(5) . ?
Br2 C6 1.897(5) . ?
C1 C2 1.375(7) . ?
C1 C9 1.393(7) . ?
C1 H1 0.9400 . ?
C2 C3 1.388(7) . ?
C2 H2 0.9400 . ?
C3 C4 1.380(7) . ?
C4 C4A 1.385(7) . ?
C4 H4 0.9400 . ?
C4A C9 1.418(7) . ?
C4A C4B 1.443(7) . ?
C4B C5 1.383(7) . ?
C4B C8A 1.403(7) . ?
C5 C6 1.385(7) . ?
C5 H5 0.9400 . ?
C6 C7 1.387(8) . ?
C7 C8 1.379(7) . ?
C7 H7 0.9400 . ?
C8 C8A 1.393(7) . ?
C8 H8 0.9400 . ?
C8A N9 1.409(6) . ?
C9 N9 1.387(6) . ?
N9 C10 1.424(6) . ?
C10 C12 1.382(7) 7_445 ?
C10 C11 1.394(7) . ?
C11 C12 1.376(7) . ?
C11 H11 0.9400 . ?
C12 C10 1.381(7) 7_445 ?
C12 H12 0.9400 . ?

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 C9 118.4(5) . . ?
C2 C1 H1 120.8 . . ?
C9 C1 H1 120.8 . . ?
C1 C2 C3 120.6(5) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 122.3(5) . . ?
C4 C3 Br1 119.5(4) . . ?
C2 C3 Br1 118.2(4) . . ?
C3 C4 C4A 117.7(5) . . ?
C3 C4 H4 121.1 . . ?
C4A C4 H4 121.1 . . ?
C4 C4A C9 120.4(4) . . ?
C4 C4A C4B 132.9(4) . . ?
C9 C4A C4B 106.7(4) . . ?
C5 C4B C8A 119.6(5) . . ?
C5 C4B C4A 133.4(5) . . ?
C8A C4B C4A 107.0(4) . . ?
C4B C5 C6 118.5(5) . . ?
C4B C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C7 121.6(5) . . ?
C5 C6 Br2 119.2(4) . . ?
C7 C6 Br2 119.2(4) . . ?
C8 C7 C6 120.8(5) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C8A 117.6(5) . . ?
C7 C8 H8 121.2 . . ?
C8A C8 H8 121.2 . . ?
C8 C8A C4B 121.8(5) . . ?
C8 C8A N9 129.1(5) . . ?
C4B C8A N9 109.1(4) . . ?
N9 C9 C1 130.3(5) . . ?
N9 C9 C4A 109.2(4) . . ?
C1 C9 C4A 120.5(5) . . ?
C9 N9 C8A 108.0(4) . . ?
C9 N9 C10 124.6(4) . . ?
C8A N9 C10 126.4(4) . . ?
C12 C10 C11 119.0(4) 7_445 . ?
C12 C10 N9 120.6(4) 7_445 . ?
C11 C10 N9 120.4(4) . . ?
C12 C11 C10 120.3(5) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C10 120.7(5) . 7_445 ?
C11 C12 H12 119.6 . . ?
C10 C12 H12 119.6 7_445 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 Br1 0.94 2.93 3.703(5) 140.1 6
C11 H11 Br1 0.94 3.04 3.724(5) 130.9 6_545

_refine_diff_density_max         0.580
_refine_diff_density_min         -0.833
_refine_diff_density_rms         0.142




####################################################################### 
# 
# 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_225RMB16
_database_code_depnum_ccdc_archive 'CCDC 1480584'
_audit_update_record             
;
2016-05-18 deposited with the CCDC.
2016-09-26 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H16 Br4 N2'
_chemical_formula_sum            'C30 H16 Br4 N2'
_chemical_formula_weight         724.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 2/c'
_space_group_name_Hall           '-C 2yc'

_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. 
;

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

_cell_length_a                   28.7080(13)
_cell_length_b                   3.9259(2)
_cell_length_c                   22.0256(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.1165(15)
_cell_angle_gamma                90
_cell_volume                     2435.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      25.32

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.974
_exptl_crystal_F_000             1400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    6.633
_shelx_estimated_absorpt_T_min   0.211
_shelx_estimated_absorpt_T_max   0.826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4602
_exptl_absorpt_correction_T_max  0.8390
_exptl_absorpt_process_details   'SADABS-2014/5 - Bruker AXS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ-geometry diffractometer 208039-01'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            20622
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_av_R_equivalents  0.1215
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.587
_diffrn_reflns_theta_max         25.335
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2226
_reflns_number_gt                1676
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX3 v2016.1 (Bruker, 2014)'
_computing_cell_refinement       'APEX3 v2016.1 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.37A  (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2014 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0090P)²+33.3800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2226
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 -0.14417(2) 1.2709(2) 0.37292(3) 0.0469(2) Uani 1 1 d . . . . .
Br2 Br 0.02652(2) 0.62004(19) 0.11048(3) 0.0422(2) Uani 1 1 d . . . . .
C1 C -0.2055(2) 1.3576(15) 0.1879(2) 0.0257(13) Uani 1 1 d . . . . .
H1 H -0.2344 1.4368 0.1648 0.031 Uiso 1 1 calc R U . . .
C2 C -0.1964(2) 1.3718(16) 0.2515(3) 0.0287(14) Uani 1 1 d . . . . .
H2 H -0.2193 1.4624 0.2723 0.034 Uiso 1 1 calc R U . . .
C3 C -0.1533(2) 1.2526(15) 0.2856(2) 0.0247(13) Uani 1 1 d . . . . .
C4 C -0.1185(2) 1.1239(16) 0.2577(3) 0.0275(14) Uani 1 1 d . . . . .
H4 H -0.0896 1.0463 0.2813 0.033 Uiso 1 1 calc R U . . .
C4A C -0.12699(18) 1.1109(15) 0.1937(2) 0.0216(12) Uani 1 1 d . . . . .
C4B C -0.09846(18) 1.0019(15) 0.1499(2) 0.0216(12) Uani 1 1 d . . . . .
C5 C -0.0528(2) 0.8685(16) 0.1561(3) 0.0300(14) Uani 1 1 d . . . . .
H5 H -0.0341 0.8287 0.1954 0.036 Uiso 1 1 calc R U . . .
C6 C -0.0358(2) 0.7959(16) 0.1026(3) 0.0308(14) Uani 1 1 d . . . . .
C7 C -0.0628(2) 0.8513(17) 0.0445(3) 0.0308(15) Uani 1 1 d . . . . .
H7 H -0.0501 0.7982 0.0094 0.037 Uiso 1 1 calc R U . . .
C8 C -0.1080(2) 0.9834(17) 0.0371(3) 0.0313(15) Uani 1 1 d . . . . .
H8 H -0.1263 1.0240 -0.0025 0.038 Uiso 1 1 calc R U . . .
C8A C -0.12593(18) 1.0550(15) 0.0908(3) 0.0245(13) Uani 1 1 d . . . . .
N9 N -0.17005(16) 1.1868(13) 0.0963(2) 0.0277(12) Uani 1 1 d . . . . .
C9 C -0.17051(19) 1.2221(15) 0.1586(2) 0.0221(12) Uani 1 1 d . . . . .
C10 C -0.21077(19) 1.2218(16) 0.0479(2) 0.0249(13) Uani 1 1 d . . . . .
C11 C -0.2071(2) 1.3866(16) -0.0068(3) 0.0274(14) Uani 1 1 d . . . . .
H11 H -0.1778 1.4798 -0.0115 0.033 Uiso 1 1 calc R U . . .
C12 C -0.24595(19) 1.4145(16) -0.0544(3) 0.0269(14) Uani 1 1 d . . . . .
H12 H -0.2431 1.5262 -0.0912 0.032 Uiso 1 1 calc R 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
Br1 C3 1.893(5) . ?
Br2 C6 1.893(6) . ?
C1 C2 1.376(8) . ?
C1 C9 1.398(8) . ?
C1 H1 0.9400 . ?
C2 C3 1.396(8) . ?
C2 H2 0.9400 . ?
C3 C4 1.367(8) . ?
C4 C4A 1.384(8) . ?
C4 H4 0.9400 . ?
C4A C9 1.406(7) . ?
C4A C4B 1.446(8) . ?
C4B C5 1.393(8) . ?
C4B C8A 1.400(8) . ?
C5 C6 1.390(8) . ?
C5 H5 0.9400 . ?
C6 C7 1.380(8) . ?
C7 C8 1.379(8) . ?
C7 H7 0.9400 . ?
C8 C8A 1.407(8) . ?
C8 H8 0.9400 . ?
C8A N9 1.395(7) . ?
N9 C9 1.382(7) . ?
N9 C10 1.429(7) . ?
C10 C12 1.385(8) 7_475 ?
C10 C11 1.390(8) . ?
C11 C12 1.380(8) . ?
C11 H11 0.9400 . ?
C12 C10 1.385(8) 7_475 ?
C12 H12 0.9400 . ?

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 C9 118.2(5) . . ?
C2 C1 H1 120.9 . . ?
C9 C1 H1 120.9 . . ?
C1 C2 C3 120.5(5) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 122.1(5) . . ?
C4 C3 Br1 120.0(4) . . ?
C2 C3 Br1 117.9(4) . . ?
C3 C4 C4A 118.0(5) . . ?
C3 C4 H4 121.0 . . ?
C4A C4 H4 121.0 . . ?
C4 C4A C9 120.8(5) . . ?
C4 C4A C4B 132.8(5) . . ?
C9 C4A C4B 106.4(4) . . ?
C5 C4B C8A 119.9(5) . . ?
C5 C4B C4A 133.5(5) . . ?
C8A C4B C4A 106.6(5) . . ?
C6 C5 C4B 118.1(5) . . ?
C6 C5 H5 120.9 . . ?
C4B C5 H5 120.9 . . ?
C7 C6 C5 121.8(6) . . ?
C7 C6 Br2 119.6(4) . . ?
C5 C6 Br2 118.6(4) . . ?
C8 C7 C6 121.2(5) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C8A 117.6(5) . . ?
C7 C8 H8 121.2 . . ?
C8A C8 H8 121.2 . . ?
N9 C8A C4B 109.4(5) . . ?
N9 C8A C8 129.2(5) . . ?
C4B C8A C8 121.3(5) . . ?
C9 N9 C8A 107.8(4) . . ?
C9 N9 C10 124.6(5) . . ?
C8A N9 C10 126.6(5) . . ?
N9 C9 C1 129.9(5) . . ?
N9 C9 C4A 109.7(5) . . ?
C1 C9 C4A 120.4(5) . . ?
C12 C10 C11 119.3(5) 7_475 . ?
C12 C10 N9 120.5(5) 7_475 . ?
C11 C10 N9 120.2(5) . . ?
C12 C11 C10 120.6(5) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C10 120.1(5) . 7_475 ?
C11 C12 H12 119.9 . . ?
C10 C12 H12 119.9 7_475 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 Br1 0.94 2.93 3.701(6) 140.1 6_575
C11 H11 Br1 0.94 3.05 3.732(6) 130.5 6_585

_refine_diff_density_max         0.619
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.146





####################################################################### 
# 
# 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_226RMB16
_database_code_depnum_ccdc_archive 'CCDC 1480585'
_audit_update_record             
;
2016-05-18 deposited with the CCDC.
2016-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H16 Br4 N2'
_chemical_formula_sum            'C30 H16 Br4 N2'
_chemical_formula_weight         724.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 2/c'
_space_group_name_Hall           '-C 2yc'

_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. 
;

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

_cell_length_a                   28.7391(14)
_cell_length_b                   3.9377(2)
_cell_length_c                   22.0251(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.1182(15)
_cell_angle_gamma                90
_cell_volume                     2445.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    269(2)
_cell_measurement_reflns_used    9989
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      25.34

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.967
_exptl_crystal_F_000             1400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    6.607
_shelx_estimated_absorpt_T_min   0.212
_shelx_estimated_absorpt_T_max   0.826
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.5094
_exptl_absorpt_correction_T_max  0.8389
_exptl_absorpt_process_details   'SADABS-2014/5 - Bruker AXS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      269(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ-geometry diffractometer 208039-01'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            17845
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_av_R_equivalents  0.1444
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.586
_diffrn_reflns_theta_max         25.337
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2233
_reflns_number_gt                1549
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX3 v2016.1 (Bruker, 2014)'
_computing_cell_refinement       'APEX3 v2016.1 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.37A  (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2014 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²+44.4242P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2233
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1269
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 -0.14409(3) 0.2257(3) 0.37277(3) 0.0532(3) Uani 1 1 d . . . . .
Br2 Br 0.02619(3) 0.8783(2) 0.11060(4) 0.0485(3) Uani 1 1 d . . . . .
C1 C -0.2056(2) 0.1445(18) 0.1879(3) 0.0288(16) Uani 1 1 d . . . . .
H1 H -0.2345 0.0717 0.1650 0.035 Uiso 1 1 calc R U . . .
C2 C -0.1962(2) 0.1260(19) 0.2515(3) 0.0307(17) Uani 1 1 d . . . . .
H2 H -0.2187 0.0338 0.2720 0.037 Uiso 1 1 calc R U . . .
C3 C -0.1533(2) 0.2442(19) 0.2855(3) 0.0308(16) Uani 1 1 d . . . . .
C4 C -0.1185(2) 0.3726(19) 0.2575(3) 0.0303(17) Uani 1 1 d . . . . .
H4 H -0.0899 0.4465 0.2809 0.036 Uiso 1 1 calc R U . . .
C4A C -0.1271(2) 0.3896(18) 0.1932(3) 0.0240(15) Uani 1 1 d . . . . .
C4B C -0.0985(2) 0.4943(18) 0.1497(3) 0.0253(16) Uani 1 1 d . . . . .
C5 C -0.0534(2) 0.6299(19) 0.1560(3) 0.0325(17) Uani 1 1 d . . . . .
H5 H -0.0353 0.6716 0.1950 0.039 Uiso 1 1 calc R U . . .
C6 C -0.0357(2) 0.7032(19) 0.1029(3) 0.0341(18) Uani 1 1 d . . . . .
C7 C -0.0633(2) 0.649(2) 0.0447(3) 0.0342(18) Uani 1 1 d . . . . .
H7 H -0.0511 0.7040 0.0098 0.041 Uiso 1 1 calc R U . . .
C8 C -0.1077(2) 0.516(2) 0.0373(3) 0.0330(18) Uani 1 1 d . . . . .
H8 H -0.1255 0.4745 -0.0019 0.040 Uiso 1 1 calc R U . . .
C8A C -0.1257(2) 0.4452(19) 0.0908(3) 0.0290(17) Uani 1 1 d . . . . .
N9 N -0.17020(18) 0.3154(16) 0.0963(2) 0.0311(15) Uani 1 1 d . . . . .
C9 C -0.1707(2) 0.2751(18) 0.1591(3) 0.0252(15) Uani 1 1 d . . . . .
C10 C -0.2104(2) 0.2777(19) 0.0476(3) 0.0274(16) Uani 1 1 d . . . . .
C11 C -0.2539(2) 0.415(2) 0.0536(3) 0.0305(17) Uani 1 1 d . . . . .
H11 H -0.2565 0.5289 0.0898 0.037 Uiso 1 1 calc R U . . .
C12 C -0.2931(2) 0.385(2) 0.0069(3) 0.0312(17) Uani 1 1 d . . . . .
H12 H -0.3221 0.4742 0.0121 0.037 Uiso 1 1 calc R 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
Br1 C3 1.891(6) . ?
Br2 C6 1.884(7) . ?
C1 C2 1.376(9) . ?
C1 C9 1.388(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.393(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(10) . ?
C4 C4A 1.392(9) . ?
C4 H4 0.9300 . ?
C4A C9 1.404(9) . ?
C4A C4B 1.439(9) . ?
C4B C5 1.382(9) . ?
C4B C8A 1.392(9) . ?
C5 C6 1.393(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(10) . ?
C7 C8 1.356(10) . ?
C7 H7 0.9300 . ?
C8 C8A 1.405(9) . ?
C8 H8 0.9300 . ?
C8A N9 1.404(8) . ?
N9 C9 1.395(8) . ?
N9 C10 1.426(8) . ?
C10 C12 1.382(9) 7_455 ?
C10 C11 1.390(9) . ?
C11 C12 1.377(9) . ?
C11 H11 0.9300 . ?
C12 C10 1.382(9) 7_455 ?
C12 H12 0.9300 . ?

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 C9 118.0(6) . . ?
C2 C1 H1 121.0 . . ?
C9 C1 H1 121.0 . . ?
C1 C2 C3 120.6(6) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 122.0(6) . . ?
C4 C3 Br1 120.0(5) . . ?
C2 C3 Br1 118.0(5) . . ?
C3 C4 C4A 118.3(6) . . ?
C3 C4 H4 120.8 . . ?
C4A C4 H4 120.8 . . ?
C4 C4A C9 119.6(6) . . ?
C4 C4A C4B 132.8(6) . . ?
C9 C4A C4B 107.5(5) . . ?
C5 C4B C8A 119.6(6) . . ?
C5 C4B C4A 133.5(6) . . ?
C8A C4B C4A 106.8(5) . . ?
C4B C5 C6 118.9(6) . . ?
C4B C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C7 C6 C5 120.3(6) . . ?
C7 C6 Br2 120.1(5) . . ?
C5 C6 Br2 119.5(5) . . ?
C8 C7 C6 121.9(6) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C8A 117.7(6) . . ?
C7 C8 H8 121.1 . . ?
C8A C8 H8 121.1 . . ?
C4B C8A N9 109.2(5) . . ?
C4B C8A C8 121.5(6) . . ?
N9 C8A C8 129.3(6) . . ?
C9 N9 C8A 108.0(5) . . ?
C9 N9 C10 124.9(5) . . ?
C8A N9 C10 126.5(5) . . ?
C1 C9 N9 130.0(6) . . ?
C1 C9 C4A 121.5(6) . . ?
N9 C9 C4A 108.4(6) . . ?
C12 C10 C11 118.8(6) 7_455 . ?
C12 C10 N9 121.1(6) 7_455 . ?
C11 C10 N9 120.1(6) . . ?
C12 C11 C10 121.1(6) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C10 120.1(6) . 7_455 ?
C11 C12 H12 120.0 . . ?
C10 C12 H12 120.0 7_455 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 Br1 0.93 2.95 3.714(7) 139.8 6_565
C12 H12 Br1 0.93 3.05 3.731(7) 131.3 4_455

_refine_diff_density_max         0.767
_refine_diff_density_min         -0.935
_refine_diff_density_rms         0.156





