# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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. 
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#######################################################################

data_190RMB17RAT
_database_code_depnum_ccdc_archive 'CCDC 1869538'
loop_
_audit_author_name
_audit_author_address
'Rub?n Alfredo Toscano'
;National Autonomous University of Mexico
Mexico
;
_audit_update_record             
;
2018-09-24 deposited with the CCDC.	2019-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          570.15
_chemical_formula_moiety         '2(C30 H18 Br2 N2), C2 H4 Cl4'
_chemical_formula_sum            'C62 H40 Br4 Cl4 N4'
_chemical_formula_weight         1302.42

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.2687(9)
_cell_length_b                   17.9615(19)
_cell_length_c                   8.2589(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.185(3)
_cell_angle_gamma                90
_cell_volume                     1371.3(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3495
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.02

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.414
_exptl_crystal_size_mid          0.338
_exptl_crystal_size_min          0.176
_exptl_absorpt_coefficient_mu    3.174
_shelx_estimated_absorpt_T_min   0.353
_shelx_estimated_absorpt_T_max   0.605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6112
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ geometry diffractometer 208039-1'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            8516
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.720
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2789
_reflns_number_gt                2051
_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 v2014.1-1(Bruker, 2014)'
_computing_cell_refinement       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (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)+(0.1113P)²+2.2138P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2789
_refine_ls_number_parameters     335
_refine_ls_number_restraints     840
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1989
_refine_ls_wR_factor_gt          0.1837
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      0.961
_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 0.3266(13) 0.3758(11) 0.010(2) 0.0630(17) Uani 0.35(3) 1 d D U P A 1
C1 C 0.632(2) 0.394(3) 0.125(5) 0.053(2) Uani 0.35(3) 1 d D U P A 1
H1 H 0.636538 0.426153 0.037425 0.064 Uiso 0.35(3) 1 calc R U P A 1
C2 C 0.5050(19) 0.357(2) 0.157(4) 0.057(2) Uani 0.35(3) 1 d D U P A 1
C3 C 0.4937(19) 0.3109(17) 0.287(3) 0.059(2) Uani 0.35(3) 1 d D U P A 1
H3 H 0.404344 0.291396 0.309060 0.071 Uiso 0.35(3) 1 calc R U P A 1
C4 C 0.619(2) 0.2927(15) 0.386(3) 0.058(2) Uani 0.35(3) 1 d D U P A 1
H4 H 0.616871 0.255176 0.463363 0.069 Uiso 0.35(3) 1 calc R U P A 1
C5 C 0.952(2) 0.2928(13) 0.583(2) 0.055(2) Uani 0.35(3) 1 d D U P A 1
H5 H 0.896837 0.262124 0.645012 0.065 Uiso 0.35(3) 1 calc R U P A 1
C6 C 1.110(3) 0.3036(11) 0.626(2) 0.054(2) Uani 0.35(3) 1 d D U P A 1
H6 H 1.154472 0.276794 0.712651 0.065 Uiso 0.35(3) 1 calc R U P A 1
C7 C 1.1853(19) 0.3483(14) 0.549(2) 0.054(2) Uani 0.35(3) 1 d D U P A 1
H7 H 1.283326 0.353853 0.578825 0.065 Uiso 0.35(3) 1 calc R U P A 1
C8 C 1.1176(16) 0.3923(15) 0.409(3) 0.053(2) Uani 0.35(3) 1 d D U P A 1
H8 H 1.170567 0.427394 0.355133 0.063 Uiso 0.35(3) 1 calc R U P A 1
N9 N 0.8848(16) 0.4146(12) 0.242(2) 0.050(2) Uani 0.35(3) 1 d D U P A 1
C10 C 0.751(3) 0.380(3) 0.230(6) 0.0520(18) Uani 0.35(3) 1 d D U P A 1
C11 C 0.745(2) 0.332(2) 0.366(4) 0.0517(18) Uani 0.35(3) 1 d D U P A 1
C12 C 0.889(2) 0.3305(18) 0.447(3) 0.0528(19) Uani 0.35(3) 1 d D U P A 1
C13 C 0.9741(18) 0.3790(19) 0.362(3) 0.0492(19) Uani 0.35(3) 1 d D U P A 1
Br1B Br 0.3258(7) 0.3838(5) -0.0208(12) 0.0644(12) Uani 0.65(3) 1 d D U P A 2
C1B C 0.6292(14) 0.3961(17) 0.109(3) 0.0534(16) Uani 0.65(3) 1 d D U P A 2
H1B H 0.641421 0.426987 0.020860 0.064 Uiso 0.65(3) 1 calc R U P A 2
C2B C 0.4968(11) 0.3632(12) 0.134(2) 0.0587(16) Uani 0.65(3) 1 d D U P A 2
C3B C 0.4767(11) 0.3128(9) 0.2551(17) 0.0606(18) Uani 0.65(3) 1 d D U P A 2
H3B H 0.389883 0.287002 0.257118 0.073 Uiso 0.65(3) 1 calc R U P A 2
C4B C 0.5887(12) 0.3007(8) 0.3755(16) 0.0597(19) Uani 0.65(3) 1 d D U P A 2
H4B H 0.573134 0.272694 0.467400 0.072 Uiso 0.65(3) 1 calc R U P A 2
C5B C 0.9102(15) 0.2886(7) 0.5876(13) 0.0558(18) Uani 0.65(3) 1 d D U P A 2
H5B H 0.847233 0.259339 0.643060 0.067 Uiso 0.65(3) 1 calc R U P A 2
C6B C 1.0644(17) 0.2951(7) 0.6449(13) 0.056(2) Uani 0.65(3) 1 d D U P A 2
H6B H 1.096624 0.270391 0.739614 0.067 Uiso 0.65(3) 1 calc R U P A 2
C7B C 1.1555(13) 0.3331(8) 0.5707(16) 0.061(2) Uani 0.65(3) 1 d D U P A 2
H7B H 1.252325 0.334681 0.609128 0.074 Uiso 0.65(3) 1 calc R U P A 2
C8B C 1.1032(11) 0.3755(8) 0.4189(15) 0.0558(18) Uani 0.65(3) 1 d D U P A 2
H8B H 1.166945 0.403525 0.361862 0.067 Uiso 0.65(3) 1 calc R U P A 2
N9B N 0.8855(9) 0.4004(7) 0.2268(12) 0.0519(19) Uani 0.65(3) 1 d D U P A 2
C10B C 0.7410(15) 0.3801(19) 0.223(3) 0.0518(14) Uani 0.65(3) 1 d D U P A 2
C11B C 0.7236(12) 0.3314(11) 0.3543(19) 0.0508(14) Uani 0.65(3) 1 d D U P A 2
C12B C 0.8615(12) 0.3277(9) 0.4475(16) 0.0519(15) Uani 0.65(3) 1 d D U P A 2
C13B C 0.9586(11) 0.3713(10) 0.3680(18) 0.0496(14) Uani 0.65(3) 1 d D U P A 2
C14 C 0.9426(6) 0.4538(3) 0.1133(6) 0.0497(11) Uani 1 1 d . . . . .
C15 C 1.0064(6) 0.5196(3) 0.1627(6) 0.0563(13) Uani 1 1 d . . . . .
H15 H 1.010697 0.533152 0.271610 0.068 Uiso 1 1 calc R U . . .
C16 C 1.0645(6) 0.5658(3) 0.0501(7) 0.0565(13) Uani 1 1 d . . . . .
H16 H 1.108595 0.610221 0.083876 0.068 Uiso 1 1 calc R U . . .
C17 C 0.425(5) 0.496(4) 0.504(8) 0.154(7) Uani 0.25 1 d D U P B -1
H17A H 0.381275 0.448968 0.466674 0.185 Uiso 0.25 1 calc R U P B -1
H17B H 0.363883 0.518072 0.580733 0.185 Uiso 0.25 1 calc R U P B -1
Cl1 Cl 0.439(4) 0.5498(17) 0.354(3) 0.168(7) Uani 0.25 1 d D U P B -1
Cl2 Cl 0.612(3) 0.4784(13) 0.603(3) 0.145(6) Uani 0.25 1 d D U P B -1
C17B C 0.463(5) 0.478(5) 0.528(10) 0.150(6) Uani 0.25 1 d D U P C -2
H17C H 0.426047 0.431006 0.483347 0.180 Uiso 0.25 1 calc R U P C -2
H17D H 0.389180 0.500652 0.588356 0.180 Uiso 0.25 1 calc R U P C -2
Cl1B Cl 0.505(3) 0.5312(15) 0.386(3) 0.167(6) Uani 0.25 1 d D U P C -2
Cl2B Cl 0.632(2) 0.4607(14) 0.666(2) 0.118(4) Uani 0.25 1 d D U P C -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 C2 2.010(9) . ?
C1 C10 1.375(10) . ?
C1 C2 1.394(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.364(11) . ?
C3 C4 1.410(12) . ?
C3 H3 0.9300 . ?
C4 C11 1.389(10) . ?
C4 H4 0.9300 . ?
C5 C12 1.403(10) . ?
C5 C6 1.495(13) . ?
C5 H5 0.9300 . ?
C6 C7 1.268(12) . ?
C6 H6 0.9300 . ?
C7 C8 1.501(12) . ?
C7 H7 0.9300 . ?
C8 C13 1.378(11) . ?
C8 H8 0.9300 . ?
N9 C10 1.387(12) . ?
N9 C13 1.403(10) . ?
N9 C14 1.410(15) . ?
C10 C11 1.417(9) . ?
C11 C12 1.448(10) . ?
C12 C13 1.394(10) . ?
Br1B C2B 1.998(7) . ?
C1B C10B 1.377(9) . ?
C1B C2B 1.391(9) . ?
C1B H1B 0.9300 . ?
C2B C3B 1.369(10) . ?
C3B C4B 1.402(11) . ?
C3B H3B 0.9300 . ?
C4B C11B 1.390(9) . ?
C4B H4B 0.9300 . ?
C5B C12B 1.400(9) . ?
C5B C6B 1.477(12) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.276(11) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.516(11) . ?
C7B H7B 0.9300 . ?
C8B C13B 1.377(10) . ?
C8B H8B 0.9300 . ?
N9B C10B 1.386(9) . ?
N9B C13B 1.406(8) . ?
N9B C14 1.467(9) . ?
C10B C11B 1.412(8) . ?
C11B C12B 1.444(9) . ?
C12B C13B 1.393(8) . ?
C14 C15 1.370(8) . ?
C14 C16 1.391(8) 3_765 ?
C15 C16 1.385(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 Cl1 1.59(6) . ?
C17 Cl2 1.89(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17B Cl1B 1.58(6) . ?
C17B Cl2B 1.89(7) . ?
C17B H17C 0.9700 . ?
C17B H17D 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C1 C2 116.2(7) . . ?
C10 C1 H1 121.9 . . ?
C2 C1 H1 121.9 . . ?
C3 C2 C1 123.6(8) . . ?
C3 C2 Br1 118.0(7) . . ?
C1 C2 Br1 118.4(7) . . ?
C2 C3 C4 119.3(8) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C11 C4 C3 118.7(8) . . ?
C11 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C12 C5 C6 118.0(8) . . ?
C12 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C7 C6 C5 121.7(8) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 120.7(9) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C13 C8 C7 117.6(8) . . ?
C13 C8 H8 121.2 . . ?
C7 C8 H8 121.2 . . ?
C10 N9 C13 108.7(8) . . ?
C10 N9 C14 124.1(13) . . ?
C13 N9 C14 121.6(11) . . ?
C1 C10 N9 129.0(12) . . ?
C1 C10 C11 122.6(7) . . ?
N9 C10 C11 107.6(8) . . ?
C4 C11 C10 118.8(8) . . ?
C4 C11 C12 133.9(8) . . ?
C10 C11 C12 106.9(6) . . ?
C13 C12 C5 119.3(8) . . ?
C13 C12 C11 106.9(6) . . ?
C5 C12 C11 133.8(8) . . ?
C8 C13 C12 122.4(7) . . ?
C8 C13 N9 128.8(8) . . ?
C12 C13 N9 108.4(7) . . ?
C10B C1B C2B 115.9(6) . . ?
C10B C1B H1B 122.0 . . ?
C2B C1B H1B 122.0 . . ?
C3B C2B C1B 123.9(7) . . ?
C3B C2B Br1B 116.5(5) . . ?
C1B C2B Br1B 119.5(5) . . ?
C2B C3B C4B 119.1(6) . . ?
C2B C3B H3B 120.4 . . ?
C4B C3B H3B 120.4 . . ?
C11B C4B C3B 118.4(6) . . ?
C11B C4B H4B 120.8 . . ?
C3B C4B H4B 120.8 . . ?
C12B C5B C6B 118.1(6) . . ?
C12B C5B H5B 121.0 . . ?
C6B C5B H5B 121.0 . . ?
C7B C6B C5B 123.2(7) . . ?
C7B C6B H6B 118.4 . . ?
C5B C6B H6B 118.4 . . ?
C6B C7B C8B 118.8(8) . . ?
C6B C7B H7B 120.6 . . ?
C8B C7B H7B 120.6 . . ?
C13B C8B C7B 118.1(7) . . ?
C13B C8B H8B 121.0 . . ?
C7B C8B H8B 121.0 . . ?
C10B N9B C13B 109.2(5) . . ?
C10B N9B C14 123.4(6) . . ?
C13B N9B C14 126.7(6) . . ?
C1B C10B N9B 129.7(7) . . ?
C1B C10B C11B 122.1(6) . . ?
N9B C10B C11B 108.0(6) . . ?
C4B C11B C10B 119.8(6) . . ?
C4B C11B C12B 133.1(6) . . ?
C10B C11B C12B 107.0(5) . . ?
C13B C12B C5B 119.4(7) . . ?
C13B C12B C11B 107.4(5) . . ?
C5B C12B C11B 133.0(6) . . ?
C8B C13B C12B 122.3(6) . . ?
C8B C13B N9B 129.3(6) . . ?
C12B C13B N9B 108.1(6) . . ?
C15 C14 C16 119.7(4) . 3_765 ?
C15 C14 N9 112.7(11) . . ?
C16 C14 N9 127.5(11) 3_765 . ?
C15 C14 N9B 122.8(6) . . ?
C16 C14 N9B 117.4(6) 3_765 . ?
C14 C15 C16 119.8(5) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C14 120.4(5) . 3_765 ?
C15 C16 H16 119.8 . . ?
C14 C16 H16 119.8 3_765 . ?
Cl1 C17 Cl2 108(2) . . ?
Cl1 C17 H17A 110.1 . . ?
Cl2 C17 H17A 110.1 . . ?
Cl1 C17 H17B 110.1 . . ?
Cl2 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?
Cl1B C17B Cl2B 108(2) . . ?
Cl1B C17B H17C 110.1 . . ?
Cl2B C17B H17C 110.1 . . ?
Cl1B C17B H17D 110.1 . . ?
Cl2B C17B H17D 110.1 . . ?
H17C C17B H17D 108.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 2(8) . . . . ?
C10 C1 C2 Br1 180(5) . . . . ?
C1 C2 C3 C4 -6(6) . . . . ?
Br1 C2 C3 C4 176(3) . . . . ?
C2 C3 C4 C11 11(5) . . . . ?
C12 C5 C6 C7 4(4) . . . . ?
C5 C6 C7 C8 0(4) . . . . ?
C6 C7 C8 C13 -4(4) . . . . ?
C2 C1 C10 N9 -170(6) . . . . ?
C2 C1 C10 C11 -2(9) . . . . ?
C13 N9 C10 C1 -178(7) . . . . ?
C14 N9 C10 C1 -24(10) . . . . ?
C13 N9 C10 C11 12(6) . . . . ?
C14 N9 C10 C11 166(3) . . . . ?
C3 C4 C11 C10 -11(6) . . . . ?
C3 C4 C11 C12 178(4) . . . . ?
C1 C10 C11 C4 7(9) . . . . ?
N9 C10 C11 C4 177(4) . . . . ?
C1 C10 C11 C12 180(6) . . . . ?
N9 C10 C11 C12 -9(6) . . . . ?
C6 C5 C12 C13 -3(4) . . . . ?
C6 C5 C12 C11 178(4) . . . . ?
C4 C11 C12 C13 175(5) . . . . ?
C10 C11 C12 C13 3(5) . . . . ?
C4 C11 C12 C5 -6(8) . . . . ?
C10 C11 C12 C5 -178(5) . . . . ?
C7 C8 C13 C12 4(5) . . . . ?
C7 C8 C13 N9 177(3) . . . . ?
C5 C12 C13 C8 -1(5) . . . . ?
C11 C12 C13 C8 178(4) . . . . ?
C5 C12 C13 N9 -175(3) . . . . ?
C11 C12 C13 N9 5(4) . . . . ?
C10 N9 C13 C8 176(5) . . . . ?
C14 N9 C13 C8 21(5) . . . . ?
C10 N9 C13 C12 -11(5) . . . . ?
C14 N9 C13 C12 -165(3) . . . . ?
C10B C1B C2B C3B -5(4) . . . . ?
C10B C1B C2B Br1B 179(3) . . . . ?
C1B C2B C3B C4B 9(3) . . . . ?
Br1B C2B C3B C4B -174.7(15) . . . . ?
C2B C3B C4B C11B -10(3) . . . . ?
C12B C5B C6B C7B -1.8(19) . . . . ?
C5B C6B C7B C8B 1.8(18) . . . . ?
C6B C7B C8B C13B 0.2(19) . . . . ?
C2B C1B C10B N9B 176(4) . . . . ?
C2B C1B C10B C11B 2(5) . . . . ?
C13B N9B C10B C1B 180(4) . . . . ?
C14 N9B C10B C1B 9(5) . . . . ?
C13B N9B C10B C11B -6(3) . . . . ?
C14 N9B C10B C11B -176.7(17) . . . . ?
C3B C4B C11B C10B 7(3) . . . . ?
C3B C4B C11B C12B -177(2) . . . . ?
C1B C10B C11B C4B -3(5) . . . . ?
N9B C10B C11B C4B -178(2) . . . . ?
C1B C10B C11B C12B 180(3) . . . . ?
N9B C10B C11B C12B 5(3) . . . . ?
C6B C5B C12B C13B 0(2) . . . . ?
C6B C5B C12B C11B 176.5(19) . . . . ?
C4B C11B C12B C13B -179(2) . . . . ?
C10B C11B C12B C13B -2(3) . . . . ?
C4B C11B C12B C5B 4(4) . . . . ?
C10B C11B C12B C5B -179(2) . . . . ?
C7B C8B C13B C12B -2(3) . . . . ?
C7B C8B C13B N9B -174.8(17) . . . . ?
C5B C12B C13B C8B 2(3) . . . . ?
C11B C12B C13B C8B -175.2(19) . . . . ?
C5B C12B C13B N9B 176.2(16) . . . . ?
C11B C12B C13B N9B -1(2) . . . . ?
C10B N9B C13B C8B 178(3) . . . . ?
C14 N9B C13B C8B -12(3) . . . . ?
C10B N9B C13B C12B 4(3) . . . . ?
C14 N9B C13B C12B 174.9(14) . . . . ?
C10 N9 C14 C15 137(4) . . . . ?
C13 N9 C14 C15 -72(3) . . . . ?
C10 N9 C14 C16 -40(5) . . . 3_765 ?
C13 N9 C14 C16 111(2) . . . 3_765 ?
C10B N9B C14 C15 118(2) . . . . ?
C13B N9B C14 C15 -51.1(18) . . . . ?
C10B N9B C14 C16 -64(3) . . . 3_765 ?
C13B N9B C14 C16 126.3(15) . . . 3_765 ?
C16 C14 C15 C16 -0.6(9) 3_765 . . . ?
N9 C14 C15 C16 -178.0(9) . . . . ?
N9B C14 C15 C16 176.8(7) . . . . ?
C14 C15 C16 C14 0.6(9) . . . 3_765 ?

_refine_diff_density_max         1.528
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.100



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_042RMB17
_database_code_depnum_ccdc_archive 'CCDC 1869540'
loop_
_audit_author_name
_audit_author_address
'Rub?n Alfredo Toscano'
;National Autonomous University of Mexico
Mexico
;
_audit_update_record             
;
2018-09-24 deposited with the CCDC.	2019-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          584.15
_chemical_formula_moiety         'C30 H18 Br2 N2'
_chemical_formula_sum            'C30 H18 Br2 N2'
_chemical_formula_weight         566.28

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                   4.5701(2)
_cell_length_b                   30.1408(16)
_cell_length_c                   16.5121(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.4100(10)
_cell_angle_gamma                90
_cell_volume                     2272.47(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9850
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      29.90

_exptl_crystal_description       lamina
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.508
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    3.590
_shelx_estimated_absorpt_T_min   0.263
_shelx_estimated_absorpt_T_max   0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5465
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ geometry diffractometer 208039-1'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            22659
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.703
_diffrn_reflns_theta_max         30.026
_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             3338
_reflns_number_gt                2112
_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 v2014.1-1(Bruker, 2014)'
_computing_cell_refinement       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (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)+(0.0370P)²+2.8221P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3338
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0822
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 -0.67816(7) 0.43648(2) 0.49780(2) 0.05467(12) Uani 1 1 d . . . . .
C1 C 0.000000 0.51860(10) 0.250000 0.0364(8) Uani 1 2 d S T P . .
C2 C 0.0758(6) 0.54160(8) 0.32024(15) 0.0402(6) Uani 1 1 d . . . . .
H2 H 0.126975 0.526185 0.367525 0.048 Uiso 1 1 calc R U . . .
C3 C 0.0757(6) 0.58753(8) 0.32035(16) 0.0416(6) Uani 1 1 d . . . . .
H3 H 0.126451 0.602910 0.367703 0.050 Uiso 1 1 calc R U . . .
C4 C 0.000000 0.61059(11) 0.250000 0.0395(8) Uani 1 2 d S T P . .
N5 N 0.000000 0.47146(9) 0.250000 0.0378(7) Uani 1 2 d S T P . .
C6 C -0.1477(5) 0.44426(7) 0.30310(15) 0.0354(5) Uani 1 1 d . . . . .
C7 C -0.3264(5) 0.45627(9) 0.36516(15) 0.0394(6) Uani 1 1 d . . . . .
H7 H -0.365285 0.485816 0.376837 0.047 Uiso 1 1 calc R U . . .
C8 C -0.4436(6) 0.42202(9) 0.40866(15) 0.0412(6) Uani 1 1 d . . . . .
C9 C -0.3916(6) 0.37759(9) 0.39263(17) 0.0482(7) Uani 1 1 d . . . . .
H9 H -0.473511 0.355547 0.423915 0.058 Uiso 1 1 calc R U . . .
C10 C -0.2169(6) 0.36662(9) 0.32974(17) 0.0466(7) Uani 1 1 d . . . . .
H10 H -0.181791 0.336969 0.317958 0.056 Uiso 1 1 calc R U . . .
C11 C -0.0934(5) 0.39967(8) 0.28399(15) 0.0373(5) Uani 1 1 d . . . . .
N12 N 0.000000 0.65773(9) 0.250000 0.0437(7) Uani 1 2 d S T P . .
C13 C 0.1450(6) 0.68479(8) 0.19602(15) 0.0408(6) Uani 1 1 d . . . . .
C14 C 0.3231(6) 0.67326(9) 0.13354(17) 0.0496(7) Uani 1 1 d . . . . .
H14 H 0.359819 0.643695 0.121448 0.060 Uiso 1 1 calc R U . . .
C15 C 0.4437(7) 0.70702(10) 0.09003(18) 0.0579(8) Uani 1 1 d . . . . .
H15 H 0.564774 0.700051 0.047961 0.069 Uiso 1 1 calc R U . . .
C16 C 0.3892(7) 0.75135(10) 0.10735(19) 0.0567(8) Uani 1 1 d . . . . .
H16 H 0.470847 0.773454 0.076146 0.068 Uiso 1 1 calc R U . . .
C17 C 0.2166(6) 0.76277(9) 0.16984(18) 0.0497(7) Uani 1 1 d . . . . .
H17 H 0.182747 0.792472 0.181521 0.060 Uiso 1 1 calc R U . . .
C18 C 0.0919(6) 0.72946(8) 0.21586(16) 0.0408(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C8 1.907(3) . ?
C1 C2 1.383(3) 2 ?
C1 C2 1.383(3) . ?
C1 N5 1.421(4) . ?
C2 C3 1.384(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9300 . ?
C4 N12 1.421(4) . ?
N5 C6 1.395(3) . ?
N5 C6 1.395(3) 2 ?
C6 C7 1.385(3) . ?
C6 C11 1.405(3) . ?
C7 C8 1.379(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(4) . ?
C9 C10 1.376(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(3) . ?
C10 H10 0.9300 . ?
C11 C11 1.438(5) 2 ?
N12 C13 1.396(3) . ?
N12 C13 1.396(3) 2 ?
C13 C14 1.385(4) . ?
C13 C18 1.409(3) . ?
C14 C15 1.374(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.369(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.395(4) . ?
C17 H17 0.9300 . ?
C18 C18 1.434(5) 2 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C2 119.8(3) 2 . ?
C2 C1 N5 120.10(15) 2 . ?
C2 C1 N5 120.10(15) . . ?
C1 C2 C3 120.2(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C3 119.8(3) . 2 ?
C3 C4 N12 120.12(15) . . ?
C3 C4 N12 120.13(15) 2 . ?
C6 N5 C6 108.0(3) . 2 ?
C6 N5 C1 125.99(13) . . ?
C6 N5 C1 125.99(13) 2 . ?
C7 C6 N5 128.9(2) . . ?
C7 C6 C11 122.1(2) . . ?
N5 C6 C11 109.0(2) . . ?
C8 C7 C6 116.4(2) . . ?
C8 C7 H7 121.8 . . ?
C6 C7 H7 121.8 . . ?
C7 C8 C9 123.4(2) . . ?
C7 C8 Br1 118.3(2) . . ?
C9 C8 Br1 118.3(2) . . ?
C10 C9 C8 119.0(2) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 120.1(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C6 119.1(2) . . ?
C10 C11 C11 134.00(15) . 2 ?
C6 C11 C11 106.94(14) . 2 ?
C13 N12 C13 108.5(3) . 2 ?
C13 N12 C4 125.76(14) . . ?
C13 N12 C4 125.76(14) 2 . ?
C14 C13 N12 129.7(2) . . ?
C14 C13 C18 121.7(2) . . ?
N12 C13 C18 108.6(2) . . ?
C15 C14 C13 117.7(3) . . ?
C15 C14 H14 121.1 . . ?
C13 C14 H14 121.1 . . ?
C14 C15 C16 121.6(3) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.4(3) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C13 118.9(2) . . ?
C17 C18 C18 133.96(16) . 2 ?
C13 C18 C18 107.16(15) . 2 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C2 C3 0.05(18) 2 . . . ?
N5 C1 C2 C3 -179.95(17) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C3 0.05(17) . . . 2 ?
C2 C3 C4 N12 -179.95(17) . . . . ?
C2 C1 N5 C6 -126.50(17) 2 . . . ?
C2 C1 N5 C6 53.50(17) . . . . ?
C2 C1 N5 C6 53.50(17) 2 . . 2 ?
C2 C1 N5 C6 -126.50(17) . . . 2 ?
C6 N5 C6 C7 -178.8(3) 2 . . . ?
C1 N5 C6 C7 1.2(3) . . . . ?
C6 N5 C6 C11 0.18(13) 2 . . . ?
C1 N5 C6 C11 -179.82(13) . . . . ?
N5 C6 C7 C8 -179.7(2) . . . . ?
C11 C6 C7 C8 1.4(4) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
C6 C7 C8 Br1 177.40(19) . . . . ?
C7 C8 C9 C10 -0.7(4) . . . . ?
Br1 C8 C9 C10 -178.4(2) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C9 C10 C11 C6 0.4(4) . . . . ?
C9 C10 C11 C11 -179.8(4) . . . 2 ?
C7 C6 C11 C10 -1.5(4) . . . . ?
N5 C6 C11 C10 179.4(2) . . . . ?
C7 C6 C11 C11 178.6(3) . . . 2 ?
N5 C6 C11 C11 -0.4(3) . . . 2 ?
C3 C4 N12 C13 127.48(18) . . . . ?
C3 C4 N12 C13 -52.52(18) 2 . . . ?
C3 C4 N12 C13 -52.52(18) . . . 2 ?
C3 C4 N12 C13 127.48(18) 2 . . 2 ?
C13 N12 C13 C14 178.0(3) 2 . . . ?
C4 N12 C13 C14 -2.0(3) . . . . ?
C13 N12 C13 C18 0.04(13) 2 . . . ?
C4 N12 C13 C18 -179.96(13) . . . . ?
N12 C13 C14 C15 -178.9(3) . . . . ?
C18 C13 C14 C15 -1.2(4) . . . . ?
C13 C14 C15 C16 -0.3(5) . . . . ?
C14 C15 C16 C17 1.3(5) . . . . ?
C15 C16 C17 C18 -0.7(5) . . . . ?
C16 C17 C18 C13 -0.7(4) . . . . ?
C16 C17 C18 C18 179.2(4) . . . 2 ?
C14 C13 C18 C17 1.7(4) . . . . ?
N12 C13 C18 C17 179.8(2) . . . . ?
C14 C13 C18 C18 -178.3(3) . . . 2 ?
N12 C13 C18 C18 -0.1(3) . . . 2 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 Br1 0.93 3.13 3.946(3) 147.9 5_466

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.072



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: N,N-dimethylformamide'
####################################################################### 
# 
# 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_254RMB17_a
_database_code_depnum_ccdc_archive 'CCDC 1869541'
loop_
_audit_author_name
_audit_author_address
'Rub?n Alfredo Toscano'
;National Autonomous University of Mexico
Mexico
;
_audit_update_record             
;
2018-09-24 deposited with the CCDC.	2019-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          565.75
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H18 Br2 N2'
_chemical_formula_weight         566.28

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.1353(5)
_cell_length_b                   13.5027(7)
_cell_length_c                   8.2770(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.6890(10)
_cell_angle_gamma                90
_cell_volume                     1171.74(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      29.56


_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.19
_exptl_crystal_size_mid          0.274
_exptl_crystal_size_max          0.458
_exptl_absorpt_coefficient_mu    3.481
_shelx_estimated_absorpt_T_min   0.299
_shelx_estimated_absorpt_T_max   0.558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5154
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ geometry diffractometer 208039-1'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            34885
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.459
_diffrn_reflns_theta_max         29.569
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3287
_reflns_number_gt                1900
_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 v2012.10.0(Bruker, 2012)'
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (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)+(0.0468P)²+0.9628P] 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         3287
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1306
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Br01 Br 0.24716(3) 0.66582(4) 0.59210(7) 0.0905(2) Uani 1 1 d . . . . .
C1 C 0.6149(3) 0.5642(2) 0.8314(4) 0.0547(8) Uani 1 1 d . . . . .
H1 H 0.661513 0.537672 0.937801 0.066 Uiso 1 1 calc R U . . .
N002 N 0.7965(2) 0.56826(19) 0.7171(3) 0.0468(6) Uani 1 1 d . . . . .
C2 C 0.4881(3) 0.5889(3) 0.7928(5) 0.0611(8) Uani 1 1 d . . . . .
H2 H 0.448002 0.578989 0.873493 0.073 Uiso 1 1 calc R U . . .
C3 C 0.4207(3) 0.6284(2) 0.6340(5) 0.0576(8) Uani 1 1 d . . . . .
C4 C 0.4727(3) 0.6430(2) 0.5086(4) 0.0523(8) Uani 1 1 d . . . . .
H4 H 0.424283 0.668253 0.402024 0.063 Uiso 1 1 calc R U . . .
C6 C 0.7819(4) 0.6654(2) 0.2396(4) 0.0609(9) Uani 1 1 d . . . . .
H6 H 0.774446 0.687724 0.130368 0.073 Uiso 1 1 calc R U . . .
C5 C 0.6762(3) 0.6630(2) 0.2878(4) 0.0535(8) Uani 1 1 d . . . . .
H5 H 0.597503 0.683396 0.212223 0.064 Uiso 1 1 calc R U . . .
C7 C 0.8998(4) 0.6353(2) 0.3495(4) 0.0582(8) Uani 1 1 d . . . . .
H7 H 0.970067 0.637471 0.312808 0.070 Uiso 1 1 calc R U . . .
C10 C 0.6706(3) 0.5800(2) 0.7078(3) 0.0450(7) Uani 1 1 d . . . . .
C11 C 0.6007(3) 0.6189(2) 0.5453(3) 0.0437(7) Uani 1 1 d . . . . .
C12 C 0.6877(3) 0.6295(2) 0.4525(3) 0.0438(6) Uani 1 1 d . . . . .
C13 C 0.8995(3) 0.5338(2) 0.8616(3) 0.0434(6) Uani 1 1 d . . . . .
C14 C 0.8928(3) 0.4419(2) 0.9304(4) 0.0507(7) Uani 1 1 d . . . . .
H14 H 0.820863 0.402529 0.883572 0.061 Uiso 1 1 calc R U . . .
C15 C 0.9931(3) 0.4084(2) 1.0693(4) 0.0508(7) Uani 1 1 d . . . . .
H15 H 0.988346 0.346581 1.116394 0.061 Uiso 1 1 calc R U . . .
C9 C 0.8082(3) 0.5997(2) 0.5620(3) 0.0439(6) Uani 1 1 d . . . . .
C8 C 0.9148(3) 0.6021(2) 0.5129(4) 0.0526(7) Uani 1 1 d . . . . .
H8 H 0.994043 0.581997 0.587310 0.063 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
Br01 C3 1.912(3) . ?
C1 C2 1.379(5) . ?
C1 C10 1.380(4) . ?
C1 H1 0.9300 . ?
N002 C10 1.387(4) . ?
N002 C9 1.399(4) . ?
N002 C13 1.428(3) . ?
C2 C3 1.382(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(5) . ?
C4 C11 1.393(4) . ?
C4 H4 0.9300 . ?
C6 C5 1.364(5) . ?
C6 C7 1.383(5) . ?
C6 H6 0.9300 . ?
C5 C12 1.401(4) . ?
C5 H5 0.9300 . ?
C7 C8 1.381(4) . ?
C7 H7 0.9300 . ?
C10 C11 1.409(4) . ?
C11 C12 1.432(4) . ?
C12 C9 1.402(4) . ?
C13 C14 1.378(4) . ?
C13 C15 1.381(4) 3_767 ?
C14 C15 1.382(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C9 C8 1.378(4) . ?
C8 H8 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 C10 118.1(3) . . ?
C2 C1 H1 121.0 . . ?
C10 C1 H1 121.0 . . ?
C10 N002 C9 108.6(2) . . ?
C10 N002 C13 126.5(2) . . ?
C9 N002 C13 124.8(2) . . ?
C1 C2 C3 120.0(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 123.1(3) . . ?
C4 C3 Br01 119.1(3) . . ?
C2 C3 Br01 117.8(3) . . ?
C3 C4 C11 117.8(3) . . ?
C3 C4 H4 121.1 . . ?
C11 C4 H4 121.1 . . ?
C5 C6 C7 121.5(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C5 C12 119.1(3) . . ?
C6 C5 H5 120.4 . . ?
C12 C5 H5 120.4 . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C1 C10 N002 129.7(3) . . ?
C1 C10 C11 121.6(3) . . ?
N002 C10 C11 108.6(3) . . ?
C4 C11 C10 119.4(3) . . ?
C4 C11 C12 133.4(3) . . ?
C10 C11 C12 107.1(2) . . ?
C5 C12 C9 118.4(3) . . ?
C5 C12 C11 134.2(3) . . ?
C9 C12 C11 107.3(2) . . ?
C14 C13 C15 119.9(2) . 3_767 ?
C14 C13 N002 120.0(3) . . ?
C15 C13 N002 120.1(3) 3_767 . ?
C13 C14 C15 119.8(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C13 C15 C14 120.3(3) 3_767 . ?
C13 C15 H15 119.9 3_767 . ?
C14 C15 H15 119.9 . . ?
C8 C9 N002 129.3(3) . . ?
C8 C9 C12 122.3(3) . . ?
N002 C9 C12 108.4(3) . . ?
C9 C8 C7 117.7(3) . . ?
C9 C8 H8 121.2 . . ?
C7 C8 H8 121.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 Br01 0.93 3.03 3.638(3) 124.9 1_655

_refine_diff_density_max         0.421
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.058



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
####################################################################### 
# 
# 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_153RMB16
_database_code_depnum_ccdc_archive 'CCDC 1869539'
loop_
_audit_author_name
_audit_author_address
'Rub?n Alfredo Toscano'
;National Autonomous University of Mexico
Mexico
;
_audit_update_record             
;
2018-09-24 deposited with the CCDC.	2019-03-15 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          503.15
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H18 Br2 N2'
_chemical_formula_weight         566.28

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.0412(7)
_cell_length_b                   22.373(2)
_cell_length_c                   29.798(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4694.2(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      25.41

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_F_000             2256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    3.476
_shelx_estimated_absorpt_T_min   0.338
_shelx_estimated_absorpt_T_max   0.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3498
_exptl_absorpt_correction_T_max  0.8477
_exptl_absorpt_process_details   'SADABS-2014/5 - Bruker AXS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(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            28240
_diffrn_reflns_av_unetI/netI     0.0826
_diffrn_reflns_av_R_equivalents  0.1019
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.277
_diffrn_reflns_theta_max         25.413
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4326
_reflns_number_gt                2470
_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)+(0.0171P)²+21.2690P] 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         4326
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1431
_refine_ls_R_factor_gt           0.0761
_refine_ls_wR_factor_ref         0.1200
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.02599(11) 0.20083(3) 0.28456(2) 0.0580(2) Uani 1 1 d . . . . .
Br2 Br 0.21404(12) -0.16940(3) 0.35298(3) 0.0680(3) Uani 1 1 d . . . . .
C1 C 0.0636(9) 0.0824(3) 0.1777(2) 0.0439(16) Uani 1 1 d . . . . .
H1 H 0.0610 0.0844 0.1465 0.053 Uiso 1 1 calc R U . . .
C2 C 0.0433(9) 0.1334(3) 0.2037(2) 0.0471(17) Uani 1 1 d . . . . .
H2 H 0.0252 0.1703 0.1898 0.057 Uiso 1 1 calc R U . . .
C3 C 0.0497(9) 0.1301(2) 0.2500(2) 0.0406(15) Uani 1 1 d . . . . .
C4 C 0.0760(8) 0.0767(3) 0.2721(2) 0.0421(16) Uani 1 1 d . . . . .
H4 H 0.0803 0.0751 0.3033 0.051 Uiso 1 1 calc R U . . .
C4A C 0.0960(8) 0.0253(2) 0.2464(2) 0.0363(15) Uani 1 1 d . . . . .
C4B C 0.1291(8) -0.0362(2) 0.2581(2) 0.0361(15) Uani 1 1 d . . . . .
C5 C 0.1513(8) -0.0659(3) 0.2988(2) 0.0382(15) Uani 1 1 d . . . . .
H5 H 0.1462 -0.0452 0.3258 0.046 Uiso 1 1 calc R U . . .
C6 C 0.1809(9) -0.1268(3) 0.2981(2) 0.0448(17) Uani 1 1 d . . . . .
C7 C 0.1881(9) -0.1586(3) 0.2584(2) 0.0485(18) Uani 1 1 d . . . . .
H7 H 0.2069 -0.1997 0.2593 0.058 Uiso 1 1 calc R U . . .
C8 C 0.1678(9) -0.1304(3) 0.2177(2) 0.0491(17) Uani 1 1 d . . . . .
H8 H 0.1718 -0.1517 0.1910 0.059 Uiso 1 1 calc R U . . .
C8A C 0.1408(8) -0.0685(3) 0.2179(2) 0.0387(15) Uani 1 1 d . . . . .
N9 N 0.1150(7) -0.0290(2) 0.18187(16) 0.0403(13) Uani 1 1 d . . . . .
C9 C 0.0879(8) 0.0284(3) 0.1996(2) 0.0387(15) Uani 1 1 d . . . . .
C10 C 0.1134(9) -0.0451(3) 0.1358(2) 0.0425(16) Uani 1 1 d . . . . .
C11 C -0.0290(10) -0.0257(3) 0.1070(2) 0.0474(17) Uani 1 1 d . . . . .
H11 H -0.1222 0.0003 0.1174 0.057 Uiso 1 1 calc R U . . .
C12 C -0.0323(9) -0.0451(3) 0.0631(2) 0.0489(17) Uani 1 1 d . . . . .
H12 H -0.1263 -0.0314 0.0437 0.059 Uiso 1 1 calc R U . . .
C13 C 0.1041(10) -0.0849(3) 0.0476(2) 0.0484(17) Uani 1 1 d . . . . .
C14 C 0.2477(10) -0.1029(3) 0.0756(2) 0.0530(18) Uani 1 1 d . . . . .
H14 H 0.3411 -0.1288 0.0651 0.064 Uiso 1 1 calc R U . . .
C15 C 0.2534(10) -0.0826(3) 0.1191(2) 0.0522(18) Uani 1 1 d . . . . .
H15 H 0.3530 -0.0943 0.1377 0.063 Uiso 1 1 calc R U . . .
C16 C 0.3972(11) -0.0688(3) -0.0279(3) 0.064(2) Uani 1 1 d . . . . .
H16 H 0.4274 -0.0462 -0.0027 0.077 Uiso 1 1 calc R U . . .
C17 C 0.5165(11) -0.0698(4) -0.0652(3) 0.073(2) Uani 1 1 d . . . . .
H17 H 0.6267 -0.0469 -0.0654 0.088 Uiso 1 1 calc R U . . .
C18 C 0.4718(12) -0.1046(4) -0.1018(2) 0.074(2) Uani 1 1 d . . . . .
H18 H 0.5541 -0.1057 -0.1262 0.088 Uiso 1 1 calc R U . . .
C19 C 0.3086(11) -0.1377(3) -0.1029(2) 0.062(2) Uani 1 1 d . . . . .
H19 H 0.2799 -0.1608 -0.1280 0.075 Uiso 1 1 calc R U . . .
C19A C 0.1876(11) -0.1368(3) -0.0670(2) 0.0502(18) Uani 1 1 d . . . . .
C19B C 0.0085(11) -0.1657(3) -0.0565(2) 0.0500(18) Uani 1 1 d . . . . .
C20 C -0.1069(12) -0.2070(3) -0.0788(2) 0.063(2) Uani 1 1 d . . . . .
H20 H -0.0741 -0.2208 -0.1072 0.076 Uiso 1 1 calc R U . . .
C21 C -0.2700(13) -0.2269(3) -0.0582(3) 0.074(2) Uani 1 1 d . . . . .
H21 H -0.3492 -0.2534 -0.0733 0.089 Uiso 1 1 calc R U . . .
C22 C -0.3188(11) -0.2083(3) -0.0152(3) 0.066(2) Uani 1 1 d . . . . .
H22 H -0.4290 -0.2229 -0.0020 0.079 Uiso 1 1 calc R U . . .
C23 C -0.2062(10) -0.1685(3) 0.0080(2) 0.0570(19) Uani 1 1 d . . . . .
H23 H -0.2371 -0.1566 0.0370 0.068 Uiso 1 1 calc R U . . .
C23A C -0.0450(10) -0.1469(3) -0.0134(2) 0.0494(17) Uani 1 1 d . . . . .
N24 N 0.0923(8) -0.1075(2) 0.00282(17) 0.0516(15) Uani 1 1 d . . . . .
C24 C 0.2341(11) -0.1022(3) -0.0295(2) 0.0512(18) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.896(6) . ?
Br2 C6 1.908(6) . ?
C1 C9 1.385(8) . ?
C1 C2 1.388(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(8) . ?
C4 C4A 1.389(8) . ?
C4 H4 0.9300 . ?
C4A C9 1.396(8) . ?
C4A C4B 1.438(7) . ?
C4B C5 1.392(8) . ?
C4B C8A 1.401(8) . ?
C5 C6 1.377(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(8) . ?
C7 C8 1.375(8) . ?
C7 H7 0.9300 . ?
C8 C8A 1.397(8) . ?
C8 H8 0.9300 . ?
C8A N9 1.402(7) . ?
N9 C9 1.401(7) . ?
N9 C10 1.418(7) . ?
C10 C15 1.387(8) . ?
C10 C11 1.390(8) . ?
C11 C12 1.379(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(8) . ?
C13 N24 1.430(8) . ?
C14 C15 1.375(8) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C24 1.371(9) . ?
C16 C17 1.394(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.367(10) . ?
C18 H18 0.9300 . ?
C19 C19A 1.369(9) . ?
C19 H19 0.9300 . ?
C19A C24 1.398(8) . ?
C19A C19B 1.451(9) . ?
C19B C20 1.398(9) . ?
C19B C23A 1.405(9) . ?
C20 C21 1.377(10) . ?
C20 H20 0.9300 . ?
C21 C22 1.389(10) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(9) . ?
C22 H22 0.9300 . ?
C23 C23A 1.389(9) . ?
C23 H23 0.9300 . ?
C23A N24 1.395(8) . ?
N24 C24 1.391(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C1 C2 117.8(6) . . ?
C9 C1 H1 121.1 . . ?
C2 C1 H1 121.1 . . ?
C3 C2 C1 120.6(6) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 122.0(6) . . ?
C4 C3 Br1 118.4(5) . . ?
C2 C3 Br1 119.6(4) . . ?
C3 C4 C4A 117.9(6) . . ?
C3 C4 H4 121.1 . . ?
C4A C4 H4 121.1 . . ?
C4 C4A C9 120.4(5) . . ?
C4 C4A C4B 132.4(6) . . ?
C9 C4A C4B 107.2(5) . . ?
C5 C4B C8A 119.4(5) . . ?
C5 C4B C4A 133.4(6) . . ?
C8A C4B C4A 107.2(5) . . ?
C6 C5 C4B 118.5(6) . . ?
C6 C5 H5 120.8 . . ?
C4B C5 H5 120.8 . . ?
C5 C6 C7 121.8(6) . . ?
C5 C6 Br2 120.0(5) . . ?
C7 C6 Br2 118.1(5) . . ?
C8 C7 C6 121.0(6) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C8A 117.7(6) . . ?
C7 C8 H8 121.1 . . ?
C8A C8 H8 121.1 . . ?
C8 C8A C4B 121.5(6) . . ?
C8 C8A N9 129.7(6) . . ?
C4B C8A N9 108.7(5) . . ?
C9 N9 C8A 107.8(5) . . ?
C9 N9 C10 126.6(5) . . ?
C8A N9 C10 125.5(5) . . ?
C1 C9 C4A 121.3(6) . . ?
C1 C9 N9 129.6(6) . . ?
C4A C9 N9 109.0(5) . . ?
C15 C10 C11 118.6(6) . . ?
C15 C10 N9 119.7(6) . . ?
C11 C10 N9 121.6(6) . . ?
C12 C11 C10 120.1(6) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.3(6) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 119.8(6) . . ?
C14 C13 N24 120.5(6) . . ?
C12 C13 N24 119.8(6) . . ?
C13 C14 C15 119.9(6) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 121.2(6) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C24 C16 C17 118.0(7) . . ?
C24 C16 H16 121.0 . . ?
C17 C16 H16 121.0 . . ?
C18 C17 C16 120.2(8) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 121.2(7) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C19A 119.7(7) . . ?
C18 C19 H19 120.1 . . ?
C19A C19 H19 120.1 . . ?
C19 C19A C24 119.2(7) . . ?
C19 C19A C19B 134.5(7) . . ?
C24 C19A C19B 106.2(6) . . ?
C20 C19B C23A 118.5(7) . . ?
C20 C19B C19A 134.3(7) . . ?
C23A C19B C19A 107.2(6) . . ?
C21 C20 C19B 119.1(7) . . ?
C21 C20 H20 120.4 . . ?
C19B C20 H20 120.4 . . ?
C20 C21 C22 121.4(7) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C23 C22 C21 121.0(8) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C23A 117.7(7) . . ?
C22 C23 H23 121.2 . . ?
C23A C23 H23 121.2 . . ?
C23 C23A N24 128.9(6) . . ?
C23 C23A C19B 122.3(7) . . ?
N24 C23A C19B 108.7(6) . . ?
C24 N24 C23A 108.2(5) . . ?
C24 N24 C13 125.0(6) . . ?
C23A N24 C13 125.9(6) . . ?
C16 C24 N24 128.6(7) . . ?
C16 C24 C19A 121.6(7) . . ?
N24 C24 C19A 109.7(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 Br1 0.93 3.06 3.716(6) 129.2 3_545
C7 H7 Br1 0.93 3.01 3.815(6) 145.8 8_655
C15 H15 Br2 0.93 3.06 3.870(7) 146.5 6_656

_refine_diff_density_max         0.546
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.098



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_253RMB17_a
_database_code_depnum_ccdc_archive 'CCDC 1896659'
loop_
_audit_author_name
_audit_author_address
'Ruben Alfredo Toscano '
;UNAM 
Mexico
;
_audit_update_record             
;
2019-02-11 deposited with the CCDC.	2019-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H18 Br2 N2'
_chemical_formula_weight         566.28

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.2718(16)
_cell_length_b                   17.063(3)
_cell_length_c                   8.0988(14)
_cell_angle_alpha                90
_cell_angle_beta                 96.262(5)
_cell_angle_gamma                90
_cell_volume                     1273.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9906
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      30.00

_exptl_crystal_description       platy-prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.026
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_max          0.189
_exptl_absorpt_coefficient_mu    3.203
_shelx_estimated_absorpt_T_min   0.583
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5556
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ geometry diffractometer 208039-1'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            39214
_diffrn_reflns_av_unetI/netI     0.0872
_diffrn_reflns_av_R_equivalents  0.1438
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.210
_diffrn_reflns_theta_max         29.128
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3424
_reflns_number_gt                1652
_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 v2012.10.0(Bruker, 2012)'
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (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)+(0.0367P)²+2.5258P] 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         3424
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1714
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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 1.16367(6) 0.61617(3) 0.97023(7) 0.0654(2) Uani 1 1 d . . . . .
N1 N 0.6026(4) 0.5890(2) 0.7455(4) 0.0365(9) Uani 1 1 d . . . . .
C1 C 0.5171(4) 0.6206(2) 0.6081(5) 0.0326(9) Uani 1 1 d . . . . .
C2 C 0.3705(5) 0.6119(3) 0.5604(5) 0.0447(11) Uani 1 1 d . . . . .
H2 H 0.313125 0.580188 0.619881 0.054 Uiso 1 1 calc R U . . .
C3 C 0.3112(5) 0.6531(3) 0.4181(6) 0.0505(12) Uani 1 1 d . . . . .
H3 H 0.212960 0.648346 0.381543 0.061 Uiso 1 1 calc R U . . .
C5 C 0.5442(6) 0.7080(3) 0.3809(5) 0.0449(12) Uani 1 1 d . . . . .
H5 H 0.601053 0.739839 0.321072 0.054 Uiso 1 1 calc R U . . .
C4 C 0.3979(6) 0.7002(3) 0.3333(6) 0.0527(13) Uani 1 1 d . . . . .
H4 H 0.356452 0.727705 0.240833 0.063 Uiso 1 1 calc R U . . .
C6 C 0.6052(5) 0.6677(2) 0.5191(5) 0.0359(10) Uani 1 1 d . . . . .
C7 C 0.7499(5) 0.6645(2) 0.6057(5) 0.0360(10) Uani 1 1 d . . . . .
C8 C 0.8813(5) 0.6980(3) 0.5789(6) 0.0504(13) Uani 1 1 d . . . . .
H8 H 0.887182 0.730227 0.487335 0.061 Uiso 1 1 calc R U . . .
C9 C 1.0031(5) 0.6837(3) 0.6873(6) 0.0487(12) Uani 1 1 d . . . . .
H9 H 1.091023 0.706948 0.670543 0.058 Uiso 1 1 calc R U . . .
C10 C 0.9938(5) 0.6346(3) 0.8212(6) 0.0433(11) Uani 1 1 d . . . . .
C11 C 0.8652(5) 0.5996(2) 0.8538(5) 0.0387(11) Uani 1 1 d . . . . .
H11 H 0.860687 0.566939 0.945002 0.046 Uiso 1 1 calc R U . . .
C12 C 0.7436(4) 0.6157(2) 0.7438(5) 0.0356(9) Uani 1 1 d . . . . .
C13 C 0.5505(4) 0.5435(2) 0.8750(5) 0.0312(9) Uani 1 1 d . . . . .
C14 C 0.5688(5) 0.5703(2) 1.0364(5) 0.0370(10) Uani 1 1 d . . . . .
H14 H 0.615292 0.617852 1.061264 0.044 Uiso 1 1 calc R U . . .
C15 C 0.4819(5) 0.4732(2) 0.8394(5) 0.0375(10) Uani 1 1 d . . . . .
H15 H 0.469636 0.455039 0.730490 0.045 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 C10 1.903(5) . ?
N1 C12 1.386(5) . ?
N1 C1 1.402(5) . ?
N1 C13 1.431(5) . ?
C1 C2 1.379(6) . ?
C1 C6 1.401(6) . ?
C2 C3 1.409(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(7) . ?
C3 H3 0.9300 . ?
C5 C4 1.376(7) . ?
C5 C6 1.381(6) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C6 C7 1.445(6) . ?
C7 C8 1.384(6) . ?
C7 C12 1.400(6) . ?
C8 C9 1.374(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(6) . ?
C11 C12 1.387(6) . ?
C11 H11 0.9300 . ?
C13 C15 1.373(6) . ?
C13 C14 1.378(5) . ?
C14 C15 1.375(6) 3_667 ?
C14 H14 0.9300 . ?
C15 H15 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
C12 N1 C1 108.6(3) . . ?
C12 N1 C13 125.5(3) . . ?
C1 N1 C13 125.7(3) . . ?
C2 C1 C6 122.0(4) . . ?
C2 C1 N1 129.5(4) . . ?
C6 C1 N1 108.5(4) . . ?
C1 C2 C3 117.4(4) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 120.2(5) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C4 C5 C6 119.0(4) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C3 C4 C5 121.9(4) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C5 C6 C1 119.5(4) . . ?
C5 C6 C7 133.6(4) . . ?
C1 C6 C7 106.9(3) . . ?
C8 C7 C12 119.0(4) . . ?
C8 C7 C6 134.0(4) . . ?
C12 C7 C6 107.1(4) . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 119.5(4) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C11 122.7(4) . . ?
C9 C10 Br1 118.7(3) . . ?
C11 C10 Br1 118.5(3) . . ?
C10 C11 C12 116.7(4) . . ?
C10 C11 H11 121.7 . . ?
C12 C11 H11 121.7 . . ?
N1 C12 C11 129.1(4) . . ?
N1 C12 C7 109.0(4) . . ?
C11 C12 C7 122.0(4) . . ?
C15 C13 C14 119.7(4) . . ?
C15 C13 N1 120.3(4) . . ?
C14 C13 N1 120.0(4) . . ?
C15 C14 C13 119.9(4) 3_667 . ?
C15 C14 H14 120.0 3_667 . ?
C13 C14 H14 120.0 . . ?
C13 C15 C14 120.4(4) . 3_667 ?
C13 C15 H15 119.8 . . ?
C14 C15 H15 119.8 3_667 . ?

_refine_diff_density_max         0.551
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.079

