# Electronic Supplementary Material (ESI) for ChemComm.
# 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_brnph3pmc
_database_code_depnum_ccdc_archive 'CCDC 1899526'
loop_
_audit_author_name
_audit_author_address
'Mark D Smith'
;University of South Carolina
United States of America
;
_audit_update_record             
;
2019-02-25 deposited with the CCDC.	2019-04-18 downloaded from the CCDC.
;
_audit_creation_date             2018-02-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C54 H58 Br2 N8 O2, 8(C1 H1 Cl3)'
_chemical_formula_sum            'C62 H66 Br2 Cl24 N8 O2'
_chemical_formula_weight         1965.84
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.3182(5)
_cell_length_b                   12.4639(5)
_cell_length_c                   14.2206(5)
_cell_angle_alpha                91.288(2)
_cell_angle_beta                 105.248(2)
_cell_angle_gamma                95.864(2)
_cell_volume                     2092.67(14)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9408
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.71
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   0.675
_shelx_estimated_absorpt_T_min   0.482
_exptl_absorpt_coefficient_mu    1.780
_exptl_absorpt_correction_T_max  0.6027
_exptl_absorpt_correction_T_min  0.4947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0881 before and 0.0460 after correction.
The Ratio of minimum to maximum transmission is 0.8208.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            66320
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.159
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          
;
Unstable to solvent loss. Crystals fracture below ca. 150+/-10 K
;
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5844
_reflns_number_total             7388
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.949
_refine_diff_density_min         -1.087
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     634
_refine_ls_number_reflns         7388
_refine_ls_number_restraints     146
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0624
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0962P)²+3.9955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1705
_refine_ls_wR_factor_ref         0.1859
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl4-C32 = Cl1-C31 = Cl3-C31 = Cl6-C32 = Cl5-C32 = Cl2-C31
 1.75 with sigma of 0.02
 Cl11-C34 = Cl12-C34 = Cl8-C33 = Cl9-C33 = Cl10-C34 = Cl7-C33 = C41-Cl31 = C41-
 Cl32 = C41-Cl33
 1.75 with sigma of 0.02
 Cl17-C36 = Cl14-C35 = Cl15-C35 = Cl18-C36 = Cl13-C35 = Cl16-C36
 1.75 with sigma of 0.02
 Cl26-C39 = Cl22-C38 = Cl25-C39 = Cl23-C38 = Cl21-C37 = Cl19-C37 = Cl27-C39 =
 Cl20-C37 = Cl24-C38 = Cl28-C40 = Cl29-C40 = Cl30-C40
 1.75 with sigma of 0.02
 Cl19-Cl20 \\sim Cl20-Cl21 \\sim Cl21-Cl19 \\sim Cl22-Cl23 \\sim Cl23-Cl24
\\sim Cl24-Cl22 \\sim Cl25-
 Cl26 \\sim Cl26-Cl27 \\sim Cl27-Cl25 \\sim Cl28-Cl29 \\sim Cl29-Cl30 \\sim
Cl30-Cl28 \\sim Cl31-Cl32 \\ Cl32-Cl33 \\sim Cl33-Cl31
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C37) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C31) = Uanis(C32)
Uanis(Cl5) = Uanis(Cl2)
Uanis(Cl1) = Uanis(Cl4)
Uanis(C33) = Uanis(C34) = Uanis(C41)
Uanis(C35) = Uanis(C36)
Uanis(C38) = Uanis(C39) = Uanis(C40)
Uanis(Cl24) = Uanis(Cl29)
Uanis(Cl11) = Uanis(Cl32)
Uanis(Cl33) = Uanis(Cl9)
Uanis(Cl30) = Uanis(Cl23)
4. Others
 1*[Sof(Cl19)+Sof(Cl20)+Sof(Cl21)+Sof(C37)+Sof(H37)]+1*[Sof(Cl22)+Sof(Cl23)+
 Sof(Cl24)+Sof(C38)+Sof(H38)]+1*[Sof(Cl25)+Sof(Cl26)+Sof(Cl27)+Sof(C39)+
 Sof(H39)]+1*[Sof(Cl28)+Sof(Cl29)+Sof(Cl30)+Sof(C40)+Sof(H40)]=1 with esd of
 0.00001
 1*[Sof(Cl7)+Sof(Cl8)+Sof(Cl9)+Sof(C33)+Sof(H33)]+1*[Sof(Cl10)+Sof(Cl11)+
 Sof(Cl12)+Sof(C34)+Sof(H34)]+1*[Sof(Cl31)+Sof(Cl32)+Sof(Cl33)+Sof(C41)+
 Sof(H41)]=1 with esd of 0.00001
 Sof(Cl4)=Sof(Cl5)=Sof(Cl6)=Sof(C32)=Sof(H32)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(C31)=Sof(H31)=FVAR(1)
 Sof(Cl7)=Sof(Cl8)=Sof(Cl9)=Sof(C33)=Sof(H33)=FVAR(2)
 Sof(Cl16)=Sof(Cl17)=Sof(Cl18)=Sof(C36)=Sof(H36)=1-FVAR(3)
 Sof(Cl13)=Sof(Cl14)=Sof(Cl15)=Sof(C35)=Sof(H35)=FVAR(3)
 Sof(Cl19)=Sof(Cl20)=Sof(Cl21)=Sof(C37)=Sof(H37)=FVAR(4)
 Sof(Cl22)=Sof(Cl23)=Sof(Cl24)=Sof(C38)=Sof(H38)=FVAR(5)
 Sof(Cl25)=Sof(Cl26)=Sof(Cl27)=Sof(C39)=Sof(H39)=FVAR(6)
 Sof(Cl28)=Sof(Cl29)=Sof(Cl30)=Sof(C40)=Sof(H40)=FVAR(7)
 Sof(Cl10)=Sof(Cl11)=Sof(Cl12)=Sof(C34)=Sof(H34)=FVAR(8)
 Sof(Cl31)=Sof(Cl32)=Sof(Cl33)=Sof(C41)=Sof(H41)=FVAR(9)
5.a Ternary CH refined with riding coordinates:
 C31(H31), C32(H32), C33(H33), C34(H34), C41(H41), C35(H35), C36(H36),
 C37(H37), C38(H38), C39(H39), C40(H40)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C23(H23A,H23B)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16),
 C18(H18), C19(H19), C21(H21), C22(H22)
5.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.09339(5) 0.13596(4) 1.15419(4) 0.0708(2) Uani 1 1 d . . . . .
O1 O 0.2141(2) 0.1660(2) 0.4472(2) 0.0456(7) Uani 1 1 d . . . . .
N1 N 0.1306(2) 0.3156(2) 0.4703(2) 0.0328(7) Uani 1 1 d . . . . .
N2 N 0.2496(2) 0.2440(2) 0.6007(2) 0.0371(7) Uani 1 1 d . . . . .
N3 N 0.1980(2) 0.4231(2) 0.6234(2) 0.0336(7) Uani 1 1 d . . . . .
N4 N 0.7713(3) 0.3397(3) 0.8256(2) 0.0433(8) Uani 1 1 d . . . . .
C1 C 0.1984(3) 0.2368(3) 0.5033(3) 0.0341(8) Uani 1 1 d . . . . .
C2 C 0.1098(3) 0.4007(3) 0.5342(3) 0.0347(8) Uani 1 1 d . . . . .
H2A H 0.101258 0.467769 0.498264 0.042 Uiso 1 1 calc R . . . .
H2B H 0.037462 0.378980 0.550319 0.042 Uiso 1 1 calc R . . . .
C3 C 0.2197(3) 0.3214(3) 0.6659(3) 0.0400(9) Uani 1 1 d . . . . .
H3A H 0.151406 0.289763 0.684014 0.048 Uiso 1 1 calc R . . . .
H3B H 0.282246 0.334026 0.726390 0.048 Uiso 1 1 calc R . . . .
C4 C 0.3152(3) 0.1589(3) 0.6469(4) 0.0485(11) Uani 1 1 d . . . . .
H4A H 0.313486 0.101494 0.597080 0.058 Uiso 1 1 calc R . . . .
H4B H 0.280420 0.126345 0.696411 0.058 Uiso 1 1 calc R . . . .
C5 C 0.4365(3) 0.2026(3) 0.6951(3) 0.0368(9) Uani 1 1 d . . . . .
C6 C 0.4802(3) 0.2075(4) 0.7950(3) 0.0436(10) Uani 1 1 d . . . . .
H6 H 0.434253 0.179378 0.834886 0.052 Uiso 1 1 calc R . . . .
C7 C 0.5903(3) 0.2527(4) 0.8383(3) 0.0418(9) Uani 1 1 d . . . . .
H7 H 0.618414 0.256312 0.907352 0.050 Uiso 1 1 calc R . . . .
C8 C 0.6590(3) 0.2925(3) 0.7818(3) 0.0358(8) Uani 1 1 d . . . . .
C9 C 0.6167(3) 0.2869(3) 0.6807(3) 0.0372(8) Uani 1 1 d . . . . .
H9 H 0.663198 0.313300 0.640669 0.045 Uiso 1 1 calc R . . . .
C10 C 0.5062(3) 0.2426(3) 0.6390(3) 0.0368(8) Uani 1 1 d . . . . .
H10 H 0.477438 0.239624 0.569952 0.044 Uiso 1 1 calc R . . . .
C11 C 0.8430(3) 0.2909(3) 0.9036(3) 0.0374(9) Uani 1 1 d . . . . .
C12 C 0.8385(4) 0.1797(4) 0.9087(3) 0.0507(11) Uani 1 1 d . . . . .
H12 H 0.785144 0.134569 0.859469 0.061 Uiso 1 1 calc R . . . .
C13 C 0.9102(4) 0.1338(4) 0.9840(4) 0.0566(12) Uani 1 1 d . . . . .
H13 H 0.905730 0.057500 0.987594 0.068 Uiso 1 1 calc R . . . .
C14 C 0.9889(4) 0.2000(4) 1.0545(3) 0.0465(10) Uani 1 1 d . . . . .
C15 C 0.9940(3) 0.3101(4) 1.0523(3) 0.0433(9) Uani 1 1 d . . . . .
H15 H 1.047482 0.354702 1.101810 0.052 Uiso 1 1 calc R . . . .
C16 C 0.9199(3) 0.3559(3) 0.9768(3) 0.0388(9) Uani 1 1 d . . . . .
H16 H 0.921956 0.432244 0.975361 0.047 Uiso 1 1 calc R . . . .
C17 C 0.8166(3) 0.4285(3) 0.7818(3) 0.0368(8) Uani 1 1 d . . . . .
C18 C 0.9224(3) 0.4304(3) 0.7638(3) 0.0381(9) Uani 1 1 d . . . . .
H18 H 0.966921 0.372843 0.783475 0.046 Uiso 1 1 calc R . . . .
C19 C 0.9633(3) 0.5156(3) 0.7174(3) 0.0366(8) Uani 1 1 d . . . . .
H19 H 1.035921 0.516133 0.705996 0.044 Uiso 1 1 calc R . . . .
C20 C 0.8995(3) 0.6003(3) 0.6872(3) 0.0341(8) Uani 1 1 d . . . . .
C21 C 0.7948(3) 0.5991(3) 0.7073(3) 0.0377(9) Uani 1 1 d . . . . .
H21 H 0.750706 0.657118 0.688414 0.045 Uiso 1 1 calc R . . . .
C22 C 0.7542(3) 0.5145(3) 0.7545(3) 0.0390(9) Uani 1 1 d . . . . .
H22 H 0.682895 0.515432 0.768274 0.047 Uiso 1 1 calc R . . . .
C23 C 0.9386(3) 0.6900(3) 0.6307(3) 0.0385(9) Uani 1 1 d . . . . .
H23A H 0.934328 0.760369 0.662473 0.046 Uiso 1 1 calc R . . . .
H23B H 1.018555 0.685221 0.631657 0.046 Uiso 1 1 calc R . . . .
C24 C 0.2953(3) 0.5042(3) 0.6217(3) 0.0364(8) Uani 1 1 d . . . . .
C25 C 0.3543(4) 0.4816(3) 0.5424(3) 0.0465(10) Uani 1 1 d . . . . .
H25A H 0.382723 0.410883 0.550984 0.070 Uiso 1 1 calc GR . . . .
H25B H 0.417751 0.537637 0.547316 0.070 Uiso 1 1 calc GR . . . .
H25C H 0.300279 0.481884 0.478050 0.070 Uiso 1 1 calc GR . . . .
C26 C 0.2504(4) 0.6130(4) 0.6084(4) 0.0582(12) Uani 1 1 d . . . . .
H26A H 0.196842 0.613206 0.543797 0.087 Uiso 1 1 calc GR . . . .
H26B H 0.313440 0.669623 0.613953 0.087 Uiso 1 1 calc GR . . . .
H26C H 0.211737 0.626754 0.658820 0.087 Uiso 1 1 calc GR . . . .
C27 C 0.3827(4) 0.5061(4) 0.7212(4) 0.0568(12) Uani 1 1 d . . . . .
H27A H 0.343883 0.506399 0.773219 0.085 Uiso 1 1 calc GR . . . .
H27B H 0.436767 0.571182 0.729294 0.085 Uiso 1 1 calc GR . . . .
H27C H 0.423104 0.441953 0.724774 0.085 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.7321(4) 0.2815(2) 0.1223(2) 0.0835(9) Uani 0.783(7) 1 d D . P A 1
Cl2 Cl 0.6155(4) 0.0708(3) 0.0577(3) 0.1196(12) Uani 0.783(7) 1 d D . P A 1
Cl3 Cl 0.8010(4) 0.1047(3) 0.2306(4) 0.149(2) Uani 0.783(7) 1 d D . P A 1
C31 C 0.6794(8) 0.1586(7) 0.1593(6) 0.095(3) Uani 0.783(7) 1 d D . P A 1
H31 H 0.624959 0.169985 0.198852 0.114 Uiso 0.783(7) 1 calc R . P A 1
Cl4 Cl 0.6860(12) 0.2684(10) 0.1277(9) 0.0835(9) Uani 0.217(7) 1 d D . P A 2
Cl5 Cl 0.6599(14) 0.0391(11) 0.0732(11) 0.1196(12) Uani 0.217(7) 1 d D . P A 2
Cl6 Cl 0.7352(10) 0.1159(5) 0.2683(5) 0.073(3) Uani 0.217(7) 1 d D . P A 2
C32 C 0.739(2) 0.1445(15) 0.1465(13) 0.095(3) Uani 0.217(7) 1 d D . P A 2
H32 H 0.819021 0.150446 0.141267 0.114 Uiso 0.217(7) 1 calc R . P A 2
Cl7 Cl -0.0105(3) -0.0856(3) 0.3043(3) 0.1147(14) Uani 0.625(3) 1 d D . P B 1
Cl8 Cl 0.2181(3) -0.1266(3) 0.3779(3) 0.1002(10) Uani 0.625(3) 1 d D . P B 1
Cl9 Cl 0.0717(4) -0.1280(3) 0.5054(3) 0.0929(11) Uani 0.625(3) 1 d D . P B 1
C33 C 0.1052(9) -0.0719(13) 0.4043(7) 0.0470(12) Uani 0.625(3) 1 d D . P B 1
H33 H 0.128243 0.007079 0.420181 0.056 Uiso 0.625(3) 1 calc R . P B 1
Cl10 Cl -0.0366(4) -0.0578(6) 0.3716(6) 0.093(2) Uani 0.293(3) 1 d D . P C 2
Cl11 Cl 0.1338(9) -0.1256(6) 0.2948(6) 0.114(3) Uani 0.293(3) 1 d D . P C 2
Cl12 Cl 0.1456(8) -0.1491(6) 0.4979(5) 0.108(3) Uani 0.293(3) 1 d D . P C 2
C34 C 0.1080(18) -0.069(3) 0.3982(13) 0.0470(12) Uani 0.293(3) 1 d D . P C 2
H34 H 0.151237 0.004843 0.414198 0.056 Uiso 0.293(3) 1 calc R . P C 2
Cl31 Cl 0.2702(14) -0.1075(14) 0.4732(17) 0.085(7) Uani 0.082(3) 1 d D . P D 3
Cl32 Cl 0.087(2) -0.108(3) 0.2992(14) 0.114(3) Uani 0.082(3) 1 d D . P D 3
Cl33 Cl 0.0418(18) -0.109(3) 0.487(2) 0.0929(11) Uani 0.082(3) 1 d D . P D 3
C41 C 0.138(2) -0.064(3) 0.4218(19) 0.0470(12) Uani 0.082(3) 1 d D . P D 3
H41 H 0.146945 0.016935 0.425578 0.056 Uiso 0.082(3) 1 calc R . P D 3
Cl13 Cl 0.744(2) 0.5501(14) 0.0237(17) 0.156(7) Uani 0.326(17) 1 d D . P E 1
Cl14 Cl 0.5910(15) 0.6997(18) -0.0308(12) 0.166(8) Uani 0.326(17) 1 d D . P E 1
Cl15 Cl 0.8113(13) 0.762(2) 0.0947(10) 0.195(8) Uani 0.326(17) 1 d D . P E 1
C35 C 0.733(2) 0.6834(17) -0.009(2) 0.099(3) Uani 0.326(17) 1 d D . P E 1
H35 H 0.762537 0.699216 -0.066993 0.118 Uiso 0.326(17) 1 calc R . P E 1
Cl16 Cl 0.7873(4) 0.5805(6) 0.0751(6) 0.1137(18) Uani 0.674(17) 1 d D . P E 2
Cl17 Cl 0.5858(6) 0.6561(14) -0.0434(8) 0.211(5) Uani 0.674(17) 1 d D . P E 2
Cl18 Cl 0.7710(8) 0.8021(5) 0.0685(6) 0.134(3) Uani 0.674(17) 1 d D . P E 2
C36 C 0.7288(11) 0.6807(11) 0.0028(12) 0.099(3) Uani 0.674(17) 1 d D . P E 2
H36 H 0.762622 0.683956 -0.053844 0.118 Uiso 0.674(17) 1 calc R . P E 2
Cl19 Cl 0.3559(4) 0.1086(4) 0.3605(3) 0.0519(12) Uani 0.266(3) 1 d D . P F 1
Cl20 Cl 0.4055(5) 0.0777(6) 0.1763(4) 0.0773(18) Uani 0.266(3) 1 d D . P F 1
Cl21 Cl 0.5853(3) 0.0952(4) 0.3550(4) 0.0619(14) Uani 0.266(3) 1 d D . P F 1
C37 C 0.4444(9) 0.0377(11) 0.3023(8) 0.029(3) Uani 0.266(3) 1 d D U P F 1
H37 H 0.433876 -0.042349 0.307805 0.034 Uiso 0.266(3) 1 calc R . P F 1
Cl22 Cl 0.4445(15) 0.2450(8) 0.3186(12) 0.081(6) Uani 0.309(3) 1 d D . P G 2
Cl23 Cl 0.519(3) 0.0673(13) 0.4328(11) 0.111(4) Uani 0.309(3) 1 d D . P G 2
Cl24 Cl 0.3832(9) 0.0274(7) 0.2350(7) 0.0657(18) Uani 0.309(3) 1 d D . P G 2
C38 C 0.407(3) 0.1108(14) 0.3400(15) 0.072(3) Uani 0.309(3) 1 d D . P G 2
H38 H 0.336683 0.105868 0.363018 0.087 Uiso 0.309(3) 1 calc R . P G 2
Cl25 Cl 0.5495(8) 0.1185(9) 0.4107(8) 0.086(3) Uani 0.200(3) 1 d D . P H 3
Cl26 Cl 0.4208(10) 0.2281(11) 0.2512(11) 0.105(5) Uani 0.200(3) 1 d D . P H 3
Cl27 Cl 0.3549(10) 0.0047(8) 0.2760(16) 0.184(11) Uani 0.200(3) 1 d D . P H 3
C39 C 0.414(2) 0.1294(16) 0.3343(19) 0.072(3) Uani 0.200(3) 1 d D . P H 3
H39 H 0.364556 0.151496 0.375713 0.087 Uiso 0.200(3) 1 calc R . P H 3
Cl28 Cl 0.459(2) 0.2443(12) 0.3474(13) 0.052(3) Uani 0.226(3) 1 d D . P I 4
Cl29 Cl 0.4006(15) 0.0533(12) 0.2186(11) 0.0657(18) Uani 0.226(3) 1 d D . P I 4
Cl30 Cl 0.506(5) 0.0384(19) 0.4231(16) 0.111(4) Uani 0.226(3) 1 d D . P I 4
C40 C 0.410(3) 0.1063(19) 0.3353(17) 0.072(3) Uani 0.226(3) 1 d D . P I 4
H40 H 0.333801 0.095982 0.347934 0.087 Uiso 0.226(3) 1 calc R . P I 4


_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 C14 1.898(4) . ?
O1 C1 1.240(5) . ?
N1 C1 1.366(5) . ?
N1 C2 1.467(5) . ?
N1 C23 1.460(5) 2_666 ?
N2 C1 1.359(5) . ?
N2 C3 1.462(5) . ?
N2 C4 1.463(5) . ?
N3 C2 1.438(5) . ?
N3 C3 1.435(5) . ?
N3 C24 1.493(5) . ?
N4 C8 1.418(5) . ?
N4 C11 1.416(5) . ?
N4 C17 1.418(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.509(5) . ?
C5 C6 1.378(6) . ?
C5 C10 1.383(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.387(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.378(6) . ?
C8 C9 1.392(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(6) . ?
C11 C16 1.388(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.373(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(6) . ?
C14 C15 1.370(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(5) . ?
C17 C22 1.386(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(5) . ?
C20 C21 1.391(5) . ?
C20 C23 1.503(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.383(6) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.529(6) . ?
C24 C26 1.514(6) . ?
C24 C27 1.534(6) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
Cl1 C31 1.749(9) . ?
Cl2 C31 1.749(9) . ?
Cl3 C31 1.778(10) . ?
C31 H31 1.0000 . ?
Cl4 C32 1.737(19) . ?
Cl5 C32 1.706(18) . ?
Cl6 C32 1.789(19) . ?
C32 H32 1.0000 . ?
Cl7 C33 1.719(11) . ?
Cl8 C33 1.730(10) . ?
Cl9 C33 1.741(11) . ?
C33 H33 1.0000 . ?
Cl10 C34 1.740(19) . ?
Cl11 C34 1.736(19) . ?
Cl12 C34 1.745(19) . ?
C34 H34 1.0000 . ?
Cl31 C41 1.75(2) . ?
Cl31 Cl25 2.41(2) 2_656 ?
Cl32 C41 1.75(2) . ?
Cl33 C41 1.74(2) . ?
C41 H41 1.0000 . ?
Cl13 C35 1.744(19) . ?
Cl14 C35 1.73(2) . ?
Cl15 C35 1.74(2) . ?
C35 H35 1.0000 . ?
Cl16 C36 1.729(12) . ?
Cl17 C36 1.702(12) . ?
Cl18 C36 1.717(13) . ?
C36 H36 1.0000 . ?
Cl19 C37 1.814(11) . ?
Cl20 C37 1.823(12) . ?
Cl21 C37 1.768(11) . ?
C37 H37 1.0000 . ?
Cl22 C38 1.744(16) . ?
Cl23 C38 1.782(17) . ?
Cl24 C38 1.742(17) . ?
C38 H38 1.0000 . ?
Cl25 C39 1.76(2) . ?
Cl26 C39 1.74(2) . ?
Cl27 C39 1.740(19) . ?
C39 H39 1.0000 . ?
Cl28 C40 1.753(18) . ?
Cl29 C40 1.742(19) . ?
Cl30 Cl30 2.44(7) 2_656 ?
Cl30 C40 1.775(19) . ?
C40 H40 1.0000 . ?

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
C1 N1 C2 123.5(3) . . ?
C1 N1 C23 120.3(3) . 2_666 ?
C23 N1 C2 115.7(3) 2_666 . ?
C1 N2 C3 121.2(3) . . ?
C1 N2 C4 120.7(3) . . ?
C3 N2 C4 116.6(3) . . ?
C2 N3 C24 117.3(3) . . ?
C3 N3 C2 107.1(3) . . ?
C3 N3 C24 119.4(3) . . ?
C11 N4 C8 120.9(3) . . ?
C11 N4 C17 119.6(3) . . ?
C17 N4 C8 118.9(3) . . ?
O1 C1 N1 121.8(4) . . ?
O1 C1 N2 122.9(3) . . ?
N2 C1 N1 115.2(3) . . ?
N1 C2 H2A 108.8 . . ?
N1 C2 H2B 108.8 . . ?
N3 C2 N1 113.8(3) . . ?
N3 C2 H2A 108.8 . . ?
N3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
N2 C3 H3A 108.9 . . ?
N2 C3 H3B 108.9 . . ?
N3 C3 N2 113.3(3) . . ?
N3 C3 H3A 108.9 . . ?
N3 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
N2 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
N2 C4 C5 111.3(3) . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C6 C5 C4 121.9(4) . . ?
C6 C5 C10 118.1(3) . . ?
C10 C5 C4 120.0(4) . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.1(4) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.4(4) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 N4 120.8(3) . . ?
C7 C8 C9 119.2(3) . . ?
C9 C8 N4 120.0(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.5(4) . . ?
C10 C9 H9 120.3 . . ?
C5 C10 C9 121.7(3) . . ?
C5 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C12 C11 N4 121.7(4) . . ?
C12 C11 C16 119.0(4) . . ?
C16 C11 N4 119.2(4) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.9(4) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.2(4) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 Br1 119.0(3) . . ?
C15 C14 Br1 119.8(3) . . ?
C15 C14 C13 121.2(4) . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.2(4) . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C15 120.4(4) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 N4 121.2(4) . . ?
C22 C17 N4 120.0(3) . . ?
C22 C17 C18 118.8(4) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.4(4) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 120.9(4) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C21 118.4(4) . . ?
C19 C20 C23 121.9(3) . . ?
C21 C20 C23 119.7(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.8(4) . . ?
C22 C21 H21 119.6 . . ?
C17 C22 H22 119.7 . . ?
C21 C22 C17 120.6(4) . . ?
C21 C22 H22 119.7 . . ?
N1 C23 C20 111.5(3) 2_666 . ?
N1 C23 H23A 109.3 2_666 . ?
N1 C23 H23B 109.3 2_666 . ?
C20 C23 H23A 109.3 . . ?
C20 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
N3 C24 C25 114.8(3) . . ?
N3 C24 C26 107.1(3) . . ?
N3 C24 C27 107.6(3) . . ?
C25 C24 C27 108.2(3) . . ?
C26 C24 C25 109.8(4) . . ?
C26 C24 C27 109.2(4) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
Cl1 C31 Cl2 110.2(5) . . ?
Cl1 C31 Cl3 104.7(5) . . ?
Cl1 C31 H31 110.9 . . ?
Cl2 C31 Cl3 109.0(6) . . ?
Cl2 C31 H31 110.9 . . ?
Cl3 C31 H31 110.9 . . ?
Cl4 C32 Cl6 104.2(13) . . ?
Cl4 C32 H32 110.3 . . ?
Cl5 C32 Cl4 115.2(15) . . ?
Cl5 C32 Cl6 106.3(13) . . ?
Cl5 C32 H32 110.3 . . ?
Cl6 C32 H32 110.3 . . ?
Cl7 C33 Cl8 110.7(7) . . ?
Cl7 C33 Cl9 111.1(7) . . ?
Cl7 C33 H33 107.7 . . ?
Cl8 C33 Cl9 111.7(7) . . ?
Cl8 C33 H33 107.7 . . ?
Cl9 C33 H33 107.7 . . ?
Cl10 C34 Cl12 109.0(13) . . ?
Cl10 C34 H34 109.7 . . ?
Cl11 C34 Cl10 107.2(13) . . ?
Cl11 C34 Cl12 111.4(14) . . ?
Cl11 C34 H34 109.7 . . ?
Cl12 C34 H34 109.7 . . ?
Cl31 C41 H41 108.3 . . ?
Cl32 C41 Cl31 110.7(14) . . ?
Cl32 C41 H41 108.3 . . ?
Cl33 C41 Cl31 110.5(14) . . ?
Cl33 C41 Cl32 110.7(14) . . ?
Cl33 C41 H41 108.3 . . ?
Cl13 C35 H35 112.1 . . ?
Cl14 C35 Cl13 105.2(16) . . ?
Cl14 C35 Cl15 110.0(19) . . ?
Cl14 C35 H35 112.1 . . ?
Cl15 C35 Cl13 105.0(18) . . ?
Cl15 C35 H35 112.1 . . ?
Cl16 C36 H36 107.2 . . ?
Cl17 C36 Cl16 113.5(9) . . ?
Cl17 C36 Cl18 113.3(9) . . ?
Cl17 C36 H36 107.2 . . ?
Cl18 C36 Cl16 108.2(8) . . ?
Cl18 C36 H36 107.2 . . ?
Cl19 C37 Cl20 104.1(6) . . ?
Cl19 C37 H37 112.9 . . ?
Cl20 C37 H37 112.9 . . ?
Cl21 C37 Cl19 106.4(7) . . ?
Cl21 C37 Cl20 106.9(6) . . ?
Cl21 C37 H37 112.9 . . ?
Cl22 C38 Cl23 108.4(11) . . ?
Cl22 C38 H38 109.2 . . ?
Cl23 C38 H38 109.2 . . ?
Cl24 C38 Cl22 111.5(12) . . ?
Cl24 C38 Cl23 109.3(11) . . ?
Cl24 C38 H38 109.2 . . ?
Cl25 C39 H39 108.4 . . ?
Cl26 C39 Cl25 110.1(13) . . ?
Cl26 C39 Cl27 111.7(13) . . ?
Cl26 C39 H39 108.4 . . ?
Cl27 C39 Cl25 109.8(13) . . ?
Cl27 C39 H39 108.4 . . ?
C40 Cl30 Cl30 132(4) . 2_656 ?
Cl28 C40 Cl30 108.4(12) . . ?
Cl28 C40 H40 109.2 . . ?
Cl29 C40 Cl28 111.0(13) . . ?
Cl29 C40 Cl30 109.7(13) . . ?
Cl29 C40 H40 109.2 . . ?
Cl30 C40 H40 109.2 . . ?

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
Br1 C14 C15 C16 177.5(3) . . . . ?
N2 C4 C5 C6 112.5(4) . . . . ?
N2 C4 C5 C10 -65.4(5) . . . . ?
N4 C8 C9 C10 -178.7(4) . . . . ?
N4 C11 C12 C13 178.8(4) . . . . ?
N4 C11 C16 C15 -177.7(4) . . . . ?
N4 C17 C18 C19 177.3(3) . . . . ?
N4 C17 C22 C21 -176.8(3) . . . . ?
C1 N1 C2 N3 24.5(5) . . . . ?
C1 N2 C3 N3 -38.0(5) . . . . ?
C1 N2 C4 C5 120.5(4) . . . . ?
C2 N1 C1 O1 180.0(3) . . . . ?
C2 N1 C1 N2 -2.1(5) . . . . ?
C2 N3 C3 N2 56.5(4) . . . . ?
C2 N3 C24 C25 -54.1(4) . . . . ?
C2 N3 C24 C26 68.0(4) . . . . ?
C2 N3 C24 C27 -174.7(3) . . . . ?
C3 N2 C1 O1 -173.4(3) . . . . ?
C3 N2 C1 N1 8.7(5) . . . . ?
C3 N2 C4 C5 -73.6(5) . . . . ?
C3 N3 C2 N1 -49.9(4) . . . . ?
C3 N3 C24 C25 78.0(4) . . . . ?
C3 N3 C24 C26 -159.8(4) . . . . ?
C3 N3 C24 C27 -42.5(5) . . . . ?
C4 N2 C1 O1 -8.2(5) . . . . ?
C4 N2 C1 N1 173.9(3) . . . . ?
C4 N2 C3 N3 156.2(3) . . . . ?
C4 C5 C6 C7 -176.9(4) . . . . ?
C4 C5 C10 C9 177.7(4) . . . . ?
C5 C6 C7 C8 -1.0(6) . . . . ?
C6 C5 C10 C9 -0.3(6) . . . . ?
C6 C7 C8 N4 179.4(4) . . . . ?
C6 C7 C8 C9 0.1(6) . . . . ?
C7 C8 C9 C10 0.6(6) . . . . ?
C8 N4 C11 C12 34.7(6) . . . . ?
C8 N4 C11 C16 -145.3(4) . . . . ?
C8 N4 C17 C18 -130.8(4) . . . . ?
C8 N4 C17 C22 48.1(5) . . . . ?
C8 C9 C10 C5 -0.6(6) . . . . ?
C10 C5 C6 C7 1.0(6) . . . . ?
C11 N4 C8 C7 44.1(6) . . . . ?
C11 N4 C8 C9 -136.6(4) . . . . ?
C11 N4 C17 C18 40.7(5) . . . . ?
C11 N4 C17 C22 -140.5(4) . . . . ?
C11 C12 C13 C14 -1.1(8) . . . . ?
C12 C11 C16 C15 2.2(6) . . . . ?
C12 C13 C14 Br1 -176.4(4) . . . . ?
C12 C13 C14 C15 2.2(8) . . . . ?
C13 C14 C15 C16 -1.2(7) . . . . ?
C14 C15 C16 C11 -1.1(6) . . . . ?
C16 C11 C12 C13 -1.2(7) . . . . ?
C17 N4 C8 C7 -144.5(4) . . . . ?
C17 N4 C8 C9 34.7(6) . . . . ?
C17 N4 C11 C12 -136.6(4) . . . . ?
C17 N4 C11 C16 43.4(5) . . . . ?
C17 C18 C19 C20 -0.5(6) . . . . ?
C18 C17 C22 C21 2.1(6) . . . . ?
C18 C19 C20 C21 1.9(5) . . . . ?
C18 C19 C20 C23 -175.8(3) . . . . ?
C19 C20 C21 C22 -1.3(5) . . . . ?
C19 C20 C23 N1 109.9(4) . . . 2_666 ?
C20 C21 C22 C17 -0.7(6) . . . . ?
C21 C20 C23 N1 -67.7(4) . . . 2_666 ?
C22 C17 C18 C19 -1.5(6) . . . . ?
C23 N1 C1 O1 8.7(5) 2_666 . . . ?
C23 N1 C1 N2 -173.3(3) 2_666 . . . ?
C23 N1 C2 N3 -163.9(3) 2_666 . . . ?
C23 C20 C21 C22 176.5(3) . . . . ?
C24 N3 C2 N1 87.6(4) . . . . ?
C24 N3 C3 N2 -79.9(4) . . . . ?
Cl25 Cl31 C41 Cl32 166(3) 2_656 . . . ?
Cl25 Cl31 C41 Cl33 -71(5) 2_656 . . . ?
Cl30 Cl30 C40 Cl28 105(3) 2_656 . . . ?
Cl30 Cl30 C40 Cl29 -133(3) 2_656 . . . ?

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

data_brnph3dmc_2
_database_code_depnum_ccdc_archive 'CCDC 1899527'
loop_
_audit_author_name
_audit_author_address
'Mark D Smith'
;University of South Carolina
United States of America
;
_audit_update_record             
;
2019-02-25 deposited with the CCDC.	2019-04-18 downloaded from the CCDC.
;
_audit_creation_date             2018-08-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H36 Br2 N6 O2, C2 H5 O'
_chemical_formula_sum            'C44 H41 Br2 N6 O3'
_chemical_formula_weight         861.65
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.8633(11)
_cell_length_b                   4.6200(4)
_cell_length_c                   26.788(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.128(2)
_cell_angle_gamma                90
_cell_volume                     1932.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6443
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.065
_cell_measurement_theta_min      2.788
_shelx_estimated_absorpt_T_max   0.919
_shelx_estimated_absorpt_T_min   0.359
_exptl_absorpt_coefficient_mu    2.147
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1560 before and 0.0626 after correction.
The Ratio of minimum to maximum transmission is 0.7784.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             882
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16686
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.082
_diffrn_reflns_theta_max         25.082
_diffrn_reflns_theta_min         2.190
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2695
_reflns_number_total             3424
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0358P)²+3.8691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1001
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1S-C1S
 1.425 with sigma of 0.015
 O1S-C2S
 1.425 with sigma of 0.015
 C2S-C2S_$1
 1.5 with sigma of 0.015
 C1S-C2S
 2.36 with sigma of 0.015
 O1S-C2S_$1
 2.36 with sigma of 0.015
 N1-H1 = N2-H2
 0.84 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C1S, O1S, C2S
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: O1S(0.5) C1S(0.5) H1SA(0.5) H1SB(0.5) H1SC(0.5) C2S(0.5) H2SA(0.5)
 H2SB(0.5)
5.a Riding coordinates:
 C2S(H2SA,H2SB)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C21(H21A,H21B)
5.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20)
5.d Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.17721(2) 0.88022(9) 0.72151(2) 0.02865(14) Uani 1 1 d . . . . .
O1 O 0.60095(15) 0.8675(5) 0.33774(9) 0.0244(6) Uani 1 1 d . . . . .
N1 N 0.53281(18) 0.4361(6) 0.32006(11) 0.0194(7) Uani 1 1 d D . . . .
H1 H 0.538(2) 0.261(4) 0.3225(14) 0.023 Uiso 1 1 d DR . . . .
N2 N 0.67234(18) 0.4477(6) 0.35963(11) 0.0174(6) Uani 1 1 d D . . . .
H2 H 0.674(2) 0.271(4) 0.3594(14) 0.021 Uiso 1 1 d DR . . . .
N3 N 0.82448(17) 0.6737(7) 0.59574(10) 0.0236(7) Uani 1 1 d . . . . .
C1 C 0.6020(2) 0.5985(7) 0.33899(11) 0.0151(7) Uani 1 1 d . . . . .
C2 C 0.7543(2) 0.5857(8) 0.37828(12) 0.0180(7) Uani 1 1 d . . . . .
H2A H 0.754431 0.780503 0.362905 0.022 Uiso 1 1 calc R . . . .
H2B H 0.800263 0.471145 0.366987 0.022 Uiso 1 1 calc R . . . .
C3 C 0.7744(2) 0.6155(8) 0.43538(12) 0.0167(7) Uani 1 1 d . . . . .
C4 C 0.8507(2) 0.5137(8) 0.46312(13) 0.0201(8) Uani 1 1 d . . . . .
H4 H 0.891665 0.427355 0.445845 0.024 Uiso 1 1 calc R . . . .
C5 C 0.8684(2) 0.5353(8) 0.51566(13) 0.0206(8) Uani 1 1 d . . . . .
H5 H 0.921091 0.463678 0.533891 0.025 Uiso 1 1 calc R . . . .
C6 C 0.8094(2) 0.6612(8) 0.54150(12) 0.0200(8) Uani 1 1 d . . . . .
C7 C 0.7339(2) 0.7713(9) 0.51389(13) 0.0244(8) Uani 1 1 d . . . . .
H7 H 0.693919 0.864657 0.531069 0.029 Uiso 1 1 calc R . . . .
C8 C 0.7163(2) 0.7463(8) 0.46165(13) 0.0221(8) Uani 1 1 d . . . . .
H8 H 0.663810 0.819420 0.443437 0.027 Uiso 1 1 calc R . . . .
C9 C 0.9079(2) 0.7136(8) 0.62346(12) 0.0187(8) Uani 1 1 d . . . . .
C10 C 0.9649(2) 0.9038(8) 0.60671(13) 0.0236(8) Uani 1 1 d . . . . .
H10 H 0.948328 1.003364 0.575492 0.028 Uiso 1 1 calc R . . . .
C11 C 1.0450(2) 0.9493(8) 0.63488(13) 0.0252(9) Uani 1 1 d . . . . .
H11 H 1.083447 1.079898 0.623134 0.030 Uiso 1 1 calc R . . . .
C12 C 1.0696(2) 0.8046(8) 0.68035(12) 0.0193(8) Uani 1 1 d . . . . .
C13 C 1.0148(2) 0.6090(8) 0.69710(12) 0.0215(8) Uani 1 1 d . . . . .
H13 H 1.032113 0.507708 0.728068 0.026 Uiso 1 1 calc R . . . .
C14 C 0.9348(2) 0.5622(8) 0.66849(12) 0.0196(8) Uani 1 1 d . . . . .
H14 H 0.897591 0.424821 0.679611 0.023 Uiso 1 1 calc R . . . .
C15 C 0.7550(2) 0.6224(8) 0.62205(12) 0.0184(7) Uani 1 1 d . . . . .
C16 C 0.7491(2) 0.7745(8) 0.66587(13) 0.0214(8) Uani 1 1 d . . . . .
H16 H 0.790461 0.918180 0.678004 0.026 Uiso 1 1 calc R . . . .
C17 C 0.6826(2) 0.7174(8) 0.69215(13) 0.0204(8) Uani 1 1 d . . . . .
H17 H 0.679812 0.821308 0.722416 0.024 Uiso 1 1 calc R . . . .
C18 C 0.6205(2) 0.5118(8) 0.67510(12) 0.0180(7) Uani 1 1 d . . . . .
C19 C 0.6259(2) 0.3661(9) 0.63050(13) 0.0261(8) Uani 1 1 d . . . . .
H19 H 0.583122 0.228604 0.617512 0.031 Uiso 1 1 calc R . . . .
C20 C 0.6926(2) 0.4173(8) 0.60459(13) 0.0277(9) Uani 1 1 d . . . . .
H20 H 0.695809 0.311267 0.574597 0.033 Uiso 1 1 calc R . . . .
C21 C 0.5490(2) 0.4464(8) 0.70403(13) 0.0211(8) Uani 1 1 d . . . . .
H21A H 0.543593 0.233995 0.707169 0.025 Uiso 1 1 calc R . . . .
H21B H 0.564046 0.527450 0.738661 0.025 Uiso 1 1 calc R . . . .
O1S O 0.5140(6) 0.8389(18) 0.4704(4) 0.100(3) Uani 0.5 1 d D U P A -1
C1S C 0.5124(8) 1.138(2) 0.4772(5) 0.088(4) Uani 0.5 1 d D U P A -1
H1SA H 0.532137 1.234266 0.448800 0.133 Uiso 0.5 1 calc GR . P A -1
H1SB H 0.550119 1.189633 0.508981 0.133 Uiso 0.5 1 calc GR . P A -1
H1SC H 0.453770 1.199524 0.478667 0.133 Uiso 0.5 1 calc GR . P A -1
C2S C 0.4911(8) 0.6513(14) 0.5096(4) 0.091(4) Uani 0.5 1 d D U P A -1
H2SA H 0.431811 0.673201 0.512308 0.109 Uiso 0.5 1 d R . P A -1
H2SB H 0.526141 0.688061 0.542048 0.109 Uiso 0.5 1 d R . P A -1


_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 C12 1.895(3) . ?
O1 C1 1.243(4) . ?
N1 H1 0.816(19) . ?
N1 C1 1.353(4) . ?
N1 C21 1.449(4) 3_666 ?
N2 H2 0.816(19) . ?
N2 C1 1.348(4) . ?
N2 C2 1.456(4) . ?
N3 C6 1.432(4) . ?
N3 C9 1.411(4) . ?
N3 C15 1.429(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.513(4) . ?
C3 C4 1.386(5) . ?
C3 C8 1.392(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(5) . ?
C6 C7 1.389(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.383(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(5) . ?
C9 C14 1.395(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.375(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(5) . ?
C12 C13 1.382(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(5) . ?
C15 C20 1.390(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(5) . ?
C18 C19 1.387(5) . ?
C18 C21 1.512(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(5) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
O1S C1S 1.394(10) . ?
O1S C2S 1.457(11) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
C2S H2SA 0.9607 . ?
C2S H2SB 0.9602 . ?

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
C1 N1 H1 118(3) . . ?
C1 N1 C21 124.3(3) . 3_666 ?
C21 N1 H1 118(3) 3_666 . ?
C1 N2 H2 123(3) . . ?
C1 N2 C2 122.6(3) . . ?
C2 N2 H2 114(3) . . ?
C9 N3 C6 120.9(3) . . ?
C9 N3 C15 119.7(3) . . ?
C15 N3 C6 119.2(3) . . ?
O1 C1 N1 122.5(3) . . ?
O1 C1 N2 122.3(3) . . ?
N2 C1 N1 115.2(3) . . ?
N2 C2 H2A 108.8 . . ?
N2 C2 H2B 108.8 . . ?
N2 C2 C3 113.8(3) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 C8 118.0(3) . . ?
C8 C3 C2 120.7(3) . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.4(3) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 N3 121.1(3) . . ?
C5 C6 C7 118.9(3) . . ?
C7 C6 N3 120.0(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 H8 119.5 . . ?
C7 C8 C3 120.9(3) . . ?
C7 C8 H8 119.5 . . ?
C10 C9 N3 121.0(3) . . ?
C10 C9 C14 118.5(3) . . ?
C14 C9 N3 120.4(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 Br1 120.6(3) . . ?
C13 C12 Br1 119.0(3) . . ?
C13 C12 C11 120.4(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 H13 120.3 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 120.9(3) . . ?
C13 C14 H14 119.5 . . ?
C16 C15 N3 120.5(3) . . ?
C16 C15 C20 118.7(3) . . ?
C20 C15 N3 120.8(3) . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.4(3) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C19 117.9(3) . . ?
C17 C18 C21 121.5(3) . . ?
C19 C18 C21 120.7(3) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.2(3) . . ?
C20 C19 H19 119.4 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.6(3) . . ?
C19 C20 H20 119.7 . . ?
N1 C21 C18 113.0(3) 3_666 . ?
N1 C21 H21A 109.0 3_666 . ?
N1 C21 H21B 109.0 3_666 . ?
C18 C21 H21A 109.0 . . ?
C18 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C1S O1S C2S 118.8(10) . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
O1S C2S H2SA 111.3 . . ?
O1S C2S H2SB 111.6 . . ?
H2SA C2S H2SB 109.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.816(19) 2.08(2) 2.848(4) 157(4) 1_545 yes
N2 H2 O1 0.816(19) 2.22(3) 2.929(4) 146(4) 1_545 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C12 C13 C14 177.1(3) . . . . ?
N2 C2 C3 C4 126.8(3) . . . . ?
N2 C2 C3 C8 -53.0(5) . . . . ?
N3 C6 C7 C8 -176.4(4) . . . . ?
N3 C9 C10 C11 177.6(3) . . . . ?
N3 C9 C14 C13 -177.0(3) . . . . ?
N3 C15 C16 C17 -178.1(3) . . . . ?
N3 C15 C20 C19 179.3(3) . . . . ?
C1 N2 C2 C3 102.1(4) . . . . ?
C2 N2 C1 O1 -5.2(5) . . . . ?
C2 N2 C1 N1 175.2(3) . . . . ?
C2 C3 C4 C5 -178.6(3) . . . . ?
C2 C3 C8 C7 179.3(3) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C4 C3 C8 C7 -0.6(6) . . . . ?
C4 C5 C6 N3 177.0(3) . . . . ?
C4 C5 C6 C7 -1.7(5) . . . . ?
C5 C6 C7 C8 2.4(6) . . . . ?
C6 N3 C9 C10 39.8(5) . . . . ?
C6 N3 C9 C14 -140.2(3) . . . . ?
C6 N3 C15 C16 -144.0(3) . . . . ?
C6 N3 C15 C20 36.7(5) . . . . ?
C6 C7 C8 C3 -1.2(6) . . . . ?
C8 C3 C4 C5 1.3(5) . . . . ?
C9 N3 C6 C5 35.2(5) . . . . ?
C9 N3 C6 C7 -146.1(4) . . . . ?
C9 N3 C15 C16 40.8(5) . . . . ?
C9 N3 C15 C20 -138.4(4) . . . . ?
C9 C10 C11 C12 0.1(6) . . . . ?
C10 C9 C14 C13 2.9(5) . . . . ?
C10 C11 C12 Br1 -176.5(3) . . . . ?
C10 C11 C12 C13 1.6(5) . . . . ?
C11 C12 C13 C14 -1.0(5) . . . . ?
C12 C13 C14 C9 -1.3(5) . . . . ?
C14 C9 C10 C11 -2.3(5) . . . . ?
C15 N3 C6 C5 -139.9(4) . . . . ?
C15 N3 C6 C7 38.8(5) . . . . ?
C15 N3 C9 C10 -145.1(3) . . . . ?
C15 N3 C9 C14 34.9(5) . . . . ?
C15 C16 C17 C18 -0.9(5) . . . . ?
C16 C15 C20 C19 0.0(6) . . . . ?
C16 C17 C18 C19 -0.7(5) . . . . ?
C16 C17 C18 C21 179.1(3) . . . . ?
C17 C18 C19 C20 1.9(6) . . . . ?
C17 C18 C21 N1 105.9(4) . . . 3_666 ?
C18 C19 C20 C15 -1.6(6) . . . . ?
C19 C18 C21 N1 -74.3(4) . . . 3_666 ?
C20 C15 C16 C17 1.2(5) . . . . ?
C21 N1 C1 O1 0.8(5) 3_666 . . . ?
C21 N1 C1 N2 -179.6(3) 3_666 . . . ?
C21 C18 C19 C20 -177.9(3) . . . . ?

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

data_brnph3dmc_i
_database_code_depnum_ccdc_archive 'CCDC 1899533'
loop_
_audit_author_name
_audit_author_address
'Mark D Smith'
;University of South Carolina
United States of America
;
_audit_update_record             
;
2019-02-25 deposited with the CCDC.	2019-04-18 downloaded from the CCDC.
;
_audit_creation_date             2018-10-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H36 Br2 N6 O2, 0.5(C6 H5 I)'
_chemical_formula_sum            'C44.98 H38.48 Br2 I0.50 N6 O2'
_chemical_formula_weight         917.63
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.8680(5)
_cell_length_b                   4.6477(2)
_cell_length_c                   26.6829(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.071(2)
_cell_angle_gamma                90
_cell_volume                     1937.53(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.355
_cell_measurement_theta_min      2.607
_shelx_estimated_absorpt_T_max   0.928
_shelx_estimated_absorpt_T_min   0.606
_exptl_absorpt_coefficient_mu    2.534
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0969 before and 0.0572 after correction.
The Ratio of minimum to maximum transmission is 0.8998.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             925
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            37894
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.384
_diffrn_reflns_theta_max         26.384
_diffrn_reflns_theta_min         1.303
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3372
_reflns_number_total             3962
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3962
_refine_ls_number_restraints     90
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0320P)²+3.9374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0889
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 I1S-C1S
 2.1 with sigma of 0.01
 C7S-I2S
 2.1 with sigma of 0.01
 N2-H2 = N1-H1
 0.84 with sigma of 0.02
 C8S-I2S \\sim C12S-I2S
 with sigma of 0.01
 C2S-I1S \\sim C6S-I1S
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(I2S) \\sim Ueq, Uanis(I1S) \\sim Ueq: with sigma of 0.0075 and sigma for
terminal atoms of 0.015
Uanis(C9S) \\sim Ueq, Uanis(C10S) \\sim Ueq, Uanis(C11S) \\sim Ueq, Uanis(C5S)
\\sim Ueq, Uanis(C12S) \\sim Ueq, Uanis(C6S) \\sim Ueq, Uanis(C1S) \\sim Ueq,
Uanis(C7S) \\sim Ueq, Uanis(C2S) \\sim Ueq, Uanis(C8S) \\sim Ueq, Uanis(C3S)
\\sim Ueq, Uanis(C4S) \\sim Ueq: with sigma of 0.015 and sigma for terminal
atoms of 0.02
Uanis(C7S) = Uanis(C8S) = Uanis(C9S) = Uanis(C10S) = Uanis(C11S) = Uanis(C12S)
= Uanis(C1S) = Uanis(C2S) = Uanis(C3S) = Uanis(C4S) = Uanis(C5S) = Uanis(C6S)
4. Others
 Sof(C7S)=Sof(C8S)=Sof(H8S)=Sof(C9S)=Sof(H9S)=Sof(C10S)=Sof(H10S)=Sof(C11S)=
 Sof(H11S)=Sof(C12S)=Sof(H12S)=Sof(I2S)=FVAR(1)
 Sof(C1S)=Sof(C2S)=Sof(H2S)=Sof(C3S)=Sof(H3S)=Sof(C4S)=Sof(H4S)=Sof(C5S)=
 Sof(H5S)=Sof(C6S)=Sof(H6S)=Sof(I1S)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C21(H21A,H21B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C8S(H8S), C9S(H9S), C10S(H10S),
 C11S(H11S), C12S(H12S), C2S(H2S), C3S(H3S), C4S(H4S), C5S(H5S), C6S(H6S)
5.c Fitted hexagon refined as free rotating group:
 C7S(C8S,C9S,C10S,C11S,C12S), C1S(C2S,C3S,C4S,C5S,C6S)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.17811(2) 0.88229(8) 0.72161(2) 0.03074(11) Uani 1 1 d . . . . .
O1 O 0.60002(12) 0.8611(4) 0.33808(7) 0.0227(4) Uani 1 1 d . . . . .
N1 N 0.53235(14) 0.4316(5) 0.32091(9) 0.0192(5) Uani 1 1 d D . . . .
H1 H 0.5380(19) 0.256(4) 0.3236(12) 0.023(8) Uiso 1 1 d D . . . .
N2 N 0.67203(13) 0.4446(5) 0.35997(9) 0.0169(5) Uani 1 1 d D . . . .
H2 H 0.6687(17) 0.269(4) 0.3590(10) 0.011(7) Uiso 1 1 d D . . . .
N3 N 0.82552(14) 0.6777(6) 0.59602(8) 0.0238(5) Uani 1 1 d . . . . .
C1 C 0.60130(15) 0.5949(6) 0.33945(9) 0.0150(5) Uani 1 1 d . . . . .
C2 C 0.75397(15) 0.5829(6) 0.37800(10) 0.0182(5) Uani 1 1 d . . . . .
H2A H 0.753497 0.776401 0.362427 0.022 Uiso 1 1 calc R . . . .
H2B H 0.799653 0.469533 0.366285 0.022 Uiso 1 1 calc R . . . .
C3 C 0.77541(15) 0.6138(6) 0.43533(10) 0.0176(5) Uani 1 1 d . . . . .
C4 C 0.85053(17) 0.5060(7) 0.46317(10) 0.0216(6) Uani 1 1 d . . . . .
H4 H 0.890590 0.413600 0.445929 0.026 Uiso 1 1 calc R . . . .
C5 C 0.86850(17) 0.5304(7) 0.51582(10) 0.0238(6) Uani 1 1 d . . . . .
H5 H 0.920725 0.456300 0.534116 0.029 Uiso 1 1 calc R . . . .
C6 C 0.81056(16) 0.6626(6) 0.54193(10) 0.0199(6) Uani 1 1 d . . . . .
C7 C 0.73619(17) 0.7778(7) 0.51403(11) 0.0255(6) Uani 1 1 d . . . . .
H7 H 0.696762 0.874574 0.531145 0.031 Uiso 1 1 calc R . . . .
C8 C 0.71887(17) 0.7532(7) 0.46168(11) 0.0242(6) Uani 1 1 d . . . . .
H8 H 0.667473 0.832792 0.443297 0.029 Uiso 1 1 calc R . . . .
C9 C 0.90888(16) 0.7156(6) 0.62386(10) 0.0200(6) Uani 1 1 d . . . . .
C10 C 0.96589(19) 0.9036(7) 0.60677(11) 0.0269(6) Uani 1 1 d . . . . .
H10 H 0.949313 1.001484 0.575338 0.032 Uiso 1 1 calc R . . . .
C11 C 1.04622(19) 0.9495(7) 0.63498(11) 0.0278(7) Uani 1 1 d . . . . .
H11 H 1.084699 1.078990 0.623133 0.033 Uiso 1 1 calc R . . . .
C12 C 1.07039(16) 0.8063(6) 0.68047(10) 0.0212(6) Uani 1 1 d . . . . .
C13 C 1.01607(17) 0.6131(7) 0.69747(10) 0.0239(6) Uani 1 1 d . . . . .
H13 H 1.033670 0.512459 0.728525 0.029 Uiso 1 1 calc R . . . .
C14 C 0.93561(17) 0.5664(7) 0.66903(10) 0.0241(6) Uani 1 1 d . . . . .
H14 H 0.898267 0.431097 0.680457 0.029 Uiso 1 1 calc R . . . .
C15 C 0.75617(16) 0.6260(6) 0.62251(10) 0.0208(6) Uani 1 1 d . . . . .
C16 C 0.74907(17) 0.7799(7) 0.66569(10) 0.0258(6) Uani 1 1 d . . . . .
H16 H 0.789787 0.925234 0.677572 0.031 Uiso 1 1 calc R . . . .
C17 C 0.68238(16) 0.7233(7) 0.69201(10) 0.0240(6) Uani 1 1 d . . . . .
H17 H 0.678845 0.829607 0.721981 0.029 Uiso 1 1 calc R . . . .
C18 C 0.62156(16) 0.5172(6) 0.67566(10) 0.0189(5) Uani 1 1 d . . . . .
C19 C 0.6285(2) 0.3682(8) 0.63154(13) 0.0386(8) Uani 1 1 d . . . . .
H19 H 0.586627 0.227718 0.618957 0.046 Uiso 1 1 calc R . . . .
C20 C 0.6951(2) 0.4195(7) 0.60543(13) 0.0386(8) Uani 1 1 d . . . . .
H20 H 0.698891 0.312243 0.575595 0.046 Uiso 1 1 calc R . . . .
C21 C 0.54968(16) 0.4537(6) 0.70393(10) 0.0202(6) Uani 1 1 d . . . . .
H21A H 0.544532 0.242667 0.707404 0.024 Uiso 1 1 calc R . . . .
H21B H 0.563916 0.536052 0.738597 0.024 Uiso 1 1 calc R . . . .
C7S C 0.5027(19) 0.339(3) 0.5089(7) 0.044(2) Uani 0.0913(19) 1 d D U P A -1
C8S C 0.486(3) 0.113(3) 0.5400(9) 0.044(2) Uani 0.0913(19) 1 d DG U P A -1
H8S H 0.474037 0.151722 0.572953 0.053 Uiso 0.0913(19) 1 calc R . P A -1
C9S C 0.488(3) -0.169(3) 0.5229(12) 0.044(2) Uani 0.0913(19) 1 d G U P A -1
H9S H 0.476347 -0.323177 0.544102 0.053 Uiso 0.0913(19) 1 calc R . P A -1
C10S C 0.505(2) -0.225(3) 0.4746(11) 0.044(2) Uani 0.0913(19) 1 d G U P A -1
H10S H 0.506391 -0.418189 0.462921 0.053 Uiso 0.0913(19) 1 calc R . P A -1
C11S C 0.522(2) 0.000(4) 0.4435(9) 0.044(2) Uani 0.0913(19) 1 d G U P A -1
H11S H 0.534125 -0.038303 0.410592 0.053 Uiso 0.0913(19) 1 calc R . P A -1
C12S C 0.521(3) 0.282(4) 0.4607(8) 0.044(2) Uani 0.0913(19) 1 d DG U P A -1
H12S H 0.531814 0.436599 0.439442 0.053 Uiso 0.0913(19) 1 calc R . P A -1
I2S I 0.4887(4) 0.759(3) 0.5319(3) 0.103(3) Uani 0.0913(19) 1 d D U P A -1
C1S C 0.5016(19) 0.512(2) 0.5001(7) 0.044(2) Uani 0.1565(18) 1 d D U P B -2
C2S C 0.4864(13) 0.340(3) 0.5401(6) 0.044(2) Uani 0.1565(18) 1 d DG U P B -2
H2S H 0.473650 0.425046 0.570236 0.053 Uiso 0.1565(18) 1 calc R . P B -2
C3S C 0.4899(14) 0.042(3) 0.5360(7) 0.044(2) Uani 0.1565(18) 1 d G U P B -2
H3S H 0.479440 -0.076222 0.563373 0.053 Uiso 0.1565(18) 1 calc R . P B -2
C4S C 0.5085(17) -0.083(2) 0.4919(8) 0.044(2) Uani 0.1565(18) 1 d G U P B -2
H4S H 0.510879 -0.286932 0.489152 0.053 Uiso 0.1565(18) 1 calc R . P B -2
C5S C 0.5238(14) 0.089(3) 0.4519(6) 0.044(2) Uani 0.1565(18) 1 d G U P B -2
H5S H 0.536529 0.003625 0.421793 0.053 Uiso 0.1565(18) 1 calc R . P B -2
C6S C 0.5203(17) 0.387(3) 0.4560(6) 0.044(2) Uani 0.1565(18) 1 d DG U P B -2
H6S H 0.530739 0.504895 0.428655 0.053 Uiso 0.1565(18) 1 calc R . P B -2
I1S I 0.4972(14) 0.963(3) 0.5059(7) 0.067(4) Uani 0.1565(18) 1 d D U P B -2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.896(3) . ?
O1 C1 1.238(3) . ?
N1 H1 0.823(18) . ?
N1 C1 1.352(3) . ?
N1 C21 1.455(3) 3_666 ?
N2 H2 0.820(17) . ?
N2 C1 1.354(3) . ?
N2 C2 1.455(3) . ?
N3 C6 1.423(3) . ?
N3 C9 1.410(3) . ?
N3 C15 1.429(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.515(4) . ?
C3 C4 1.383(4) . ?
C3 C8 1.393(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(4) . ?
C6 C7 1.388(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.380(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(4) . ?
C9 C14 1.391(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(4) . ?
C12 C13 1.375(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(4) . ?
C15 C20 1.383(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.394(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.375(4) . ?
C18 C19 1.387(4) . ?
C18 C21 1.503(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(4) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C7S C8S 1.3900 . ?
C7S C12S 1.3900 . ?
C7S I2S 2.069(10) . ?
C8S H8S 0.9500 . ?
C8S C9S 1.3900 . ?
C9S H9S 0.9500 . ?
C9S C10S 1.3900 . ?
C10S H10S 0.9500 . ?
C10S C11S 1.3900 . ?
C11S H11S 0.9500 . ?
C11S C12S 1.3900 . ?
C12S H12S 0.9500 . ?
C1S C2S 1.3900 . ?
C1S C6S 1.3900 . ?
C1S I1S 2.102(10) . ?
C2S H2S 0.9500 . ?
C2S C3S 1.3900 . ?
C3S H3S 0.9500 . ?
C3S C4S 1.3900 . ?
C4S H4S 0.9500 . ?
C4S C5S 1.3900 . ?
C5S H5S 0.9500 . ?
C5S C6S 1.3900 . ?
C6S H6S 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
C1 N1 H1 117(2) . . ?
C1 N1 C21 124.3(2) . 3_666 ?
C21 N1 H1 119(2) 3_666 . ?
C1 N2 H2 117(2) . . ?
C1 N2 C2 122.4(2) . . ?
C2 N2 H2 120(2) . . ?
C6 N3 C15 119.2(2) . . ?
C9 N3 C6 121.0(2) . . ?
C9 N3 C15 119.6(2) . . ?
O1 C1 N1 122.8(2) . . ?
O1 C1 N2 122.4(2) . . ?
N1 C1 N2 114.8(2) . . ?
N2 C2 H2A 108.8 . . ?
N2 C2 H2B 108.8 . . ?
N2 C2 C3 113.9(2) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C4 C3 C2 121.9(2) . . ?
C4 C3 C8 117.9(2) . . ?
C8 C3 C2 120.2(2) . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.3(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 N3 121.5(2) . . ?
C7 C6 N3 120.0(2) . . ?
C7 C6 C5 118.5(2) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.6 . . ?
C3 C8 H8 119.4 . . ?
C7 C8 C3 121.2(3) . . ?
C7 C8 H8 119.4 . . ?
C10 C9 N3 120.6(2) . . ?
C10 C9 C14 118.7(3) . . ?
C14 C9 N3 120.7(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 Br1 120.2(2) . . ?
C13 C12 Br1 119.0(2) . . ?
C13 C12 C11 120.8(3) . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.5(3) . . ?
C14 C13 H13 120.2 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C16 C15 N3 120.6(3) . . ?
C16 C15 C20 118.7(3) . . ?
C20 C15 N3 120.6(3) . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.6(3) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C19 117.5(3) . . ?
C17 C18 C21 122.0(2) . . ?
C19 C18 C21 120.5(3) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.5(3) . . ?
C20 C19 H19 119.3 . . ?
C15 C20 C19 120.4(3) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
N1 C21 C18 113.4(2) 3_666 . ?
N1 C21 H21A 108.9 3_666 . ?
N1 C21 H21B 108.9 3_666 . ?
C18 C21 H21A 108.9 . . ?
C18 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C8S C7S C12S 120.0 . . ?
C8S C7S I2S 119.6(4) . . ?
C12S C7S I2S 120.2(4) . . ?
C7S C8S H8S 120.0 . . ?
C9S C8S C7S 120.0 . . ?
C9S C8S H8S 120.0 . . ?
C8S C9S H9S 120.0 . . ?
C8S C9S C10S 120.0 . . ?
C10S C9S H9S 120.0 . . ?
C9S C10S H10S 120.0 . . ?
C11S C10S C9S 120.0 . . ?
C11S C10S H10S 120.0 . . ?
C10S C11S H11S 120.0 . . ?
C12S C11S C10S 120.0 . . ?
C12S C11S H11S 120.0 . . ?
C7S C12S H12S 120.0 . . ?
C11S C12S C7S 120.0 . . ?
C11S C12S H12S 120.0 . . ?
C2S C1S C6S 120.0 . . ?
C2S C1S I1S 120.4(3) . . ?
C6S C1S I1S 119.6(3) . . ?
C1S C2S H2S 120.0 . . ?
C3S C2S C1S 120.0 . . ?
C3S C2S H2S 120.0 . . ?
C2S C3S H3S 120.0 . . ?
C2S C3S C4S 120.0 . . ?
C4S C3S H3S 120.0 . . ?
C3S C4S H4S 120.0 . . ?
C5S C4S C3S 120.0 . . ?
C5S C4S H4S 120.0 . . ?
C4S C5S H5S 120.0 . . ?
C4S C5S C6S 120.0 . . ?
C6S C5S H5S 120.0 . . ?
C1S C6S H6S 120.0 . . ?
C5S C6S C1S 120.0 . . ?
C5S C6S H6S 120.0 . . ?

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
_geom_hbond_publ_flag
N1 H1 O1 0.823(18) 2.09(2) 2.867(3) 158(3) 1_545 yes
N2 H2 O1 0.820(17) 2.21(2) 2.961(3) 153(3) 1_545 yes

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

data_brnph3dmc_mt2
_database_code_depnum_ccdc_archive 'CCDC 1899528'
loop_
_audit_author_name
_audit_author_address
'Mark D Smith'
;University of South Carolina
United States of America
;
_audit_update_record             
;
2019-02-25 deposited with the CCDC.	2019-04-18 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H36 Br2 N6 O2'
_chemical_formula_sum            'C42 H36 Br2 N6 O2'
_chemical_formula_weight         816.59
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.8204(7)
_cell_length_b                   4.6117(2)
_cell_length_c                   26.8694(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.316(2)
_cell_angle_gamma                90
_cell_volume                     1928.67(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.561
_cell_measurement_theta_min      2.617
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.481
_exptl_absorpt_coefficient_mu    2.145
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1468 before and 0.0588 after correction.
The Ratio of minimum to maximum transmission is 0.8644.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            28652
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        27.589
_diffrn_reflns_theta_max         27.589
_diffrn_reflns_theta_min         2.617
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3673
_reflns_number_total             4436
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4436
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0328P)²+1.5049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0775
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N1-H1 = N2-H2
 0.85 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uiso(H2) = Uiso(H1)
4.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C21(H21A,H21B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.17486(2) 0.85851(6) 0.72133(2) 0.02505(8) Uani 1 1 d . . . . .
O1 O 0.60222(9) 0.8962(3) 0.33679(6) 0.0208(3) Uani 1 1 d . . . . .
N1 N 0.53413(10) 0.4647(4) 0.31816(7) 0.0173(4) Uani 1 1 d D . . . .
H1 H 0.5400(14) 0.288(4) 0.3208(9) 0.014(4) Uiso 1 1 d D . . . .
N2 N 0.67420(10) 0.4749(4) 0.35709(6) 0.0153(3) Uani 1 1 d D . . . .
H2 H 0.6721(14) 0.299(4) 0.3562(9) 0.014(4) Uiso 1 1 d D . . . .
N3 N 0.82046(11) 0.6614(4) 0.59475(6) 0.0209(4) Uani 1 1 d . . . . .
C1 C 0.60322(12) 0.6277(4) 0.33745(7) 0.0131(4) Uani 1 1 d . . . . .
C2 C 0.75533(12) 0.6118(5) 0.37780(7) 0.0161(4) Uani 1 1 d . . . . .
H2A H 0.755518 0.810785 0.364016 0.019 Uiso 1 1 calc R . . . .
H2B H 0.802283 0.502547 0.366431 0.019 Uiso 1 1 calc R . . . .
C3 C 0.77336(12) 0.6277(4) 0.43479(7) 0.0149(4) Uani 1 1 d . . . . .
C4 C 0.84951(12) 0.5221(5) 0.46262(8) 0.0175(4) Uani 1 1 d . . . . .
H4 H 0.891283 0.440350 0.445404 0.021 Uiso 1 1 calc R . . . .
C5 C 0.86597(13) 0.5334(5) 0.51515(8) 0.0190(4) Uani 1 1 d . . . . .
H5 H 0.918366 0.458289 0.533422 0.023 Uiso 1 1 calc R . . . .
C6 C 0.80583(13) 0.6546(5) 0.54106(7) 0.0180(4) Uani 1 1 d . . . . .
C7 C 0.73003(13) 0.7657(5) 0.51333(8) 0.0203(4) Uani 1 1 d . . . . .
H7 H 0.688915 0.852435 0.530467 0.024 Uiso 1 1 calc R . . . .
C8 C 0.71395(13) 0.7512(5) 0.46119(8) 0.0186(4) Uani 1 1 d . . . . .
H8 H 0.661569 0.826619 0.442948 0.022 Uiso 1 1 calc R . . . .
C9 C 0.90431(12) 0.6978(5) 0.62284(8) 0.0170(4) Uani 1 1 d . . . . .
C10 C 0.96166(14) 0.8906(5) 0.60665(8) 0.0212(4) Uani 1 1 d . . . . .
H10 H 0.944905 0.992977 0.575777 0.025 Uiso 1 1 calc R . . . .
C11 C 1.04284(14) 0.9346(5) 0.63506(8) 0.0218(5) Uani 1 1 d . . . . .
H11 H 1.081647 1.066086 0.623801 0.026 Uiso 1 1 calc R . . . .
C12 C 1.06660(12) 0.7852(5) 0.67991(8) 0.0180(4) Uani 1 1 d . . . . .
C13 C 1.01187(13) 0.5870(5) 0.69615(8) 0.0191(4) Uani 1 1 d . . . . .
H13 H 1.029395 0.482244 0.726698 0.023 Uiso 1 1 calc R . . . .
C14 C 0.93102(13) 0.5431(5) 0.66725(8) 0.0188(4) Uani 1 1 d . . . . .
H14 H 0.893380 0.405347 0.677970 0.023 Uiso 1 1 calc R . . . .
C15 C 0.75125(12) 0.6077(5) 0.62102(8) 0.0174(4) Uani 1 1 d . . . . .
C16 C 0.74653(12) 0.7555(5) 0.66536(8) 0.0176(4) Uani 1 1 d . . . . .
H16 H 0.787986 0.899765 0.677495 0.021 Uiso 1 1 calc R . . . .
C17 C 0.68110(12) 0.6929(5) 0.69212(8) 0.0174(4) Uani 1 1 d . . . . .
H17 H 0.679249 0.792064 0.722893 0.021 Uiso 1 1 calc R . . . .
C18 C 0.61858(12) 0.4882(5) 0.67463(7) 0.0156(4) Uani 1 1 d . . . . .
C19 C 0.62223(14) 0.3496(5) 0.62921(8) 0.0220(4) Uani 1 1 d . . . . .
H19 H 0.578816 0.213729 0.616016 0.026 Uiso 1 1 calc R . . . .
C20 C 0.68800(14) 0.4056(5) 0.60278(8) 0.0227(5) Uani 1 1 d . . . . .
H20 H 0.689918 0.305634 0.572086 0.027 Uiso 1 1 calc R . . . .
C21 C 0.54885(12) 0.4163(5) 0.70429(8) 0.0181(4) Uani 1 1 d . . . . .
H21A H 0.543864 0.202924 0.706589 0.022 Uiso 1 1 calc R . . . .
H21B H 0.565454 0.492689 0.739105 0.022 Uiso 1 1 calc R . . . .


_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 C12 1.898(2) . ?
O1 C1 1.239(2) . ?
N1 H1 0.820(16) . ?
N1 C1 1.351(3) . ?
N1 C21 1.451(2) 3_666 ?
N2 H2 0.810(16) . ?
N2 C1 1.350(2) . ?
N2 C2 1.449(2) . ?
N3 C6 1.420(3) . ?
N3 C9 1.414(3) . ?
N3 C15 1.427(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.508(3) . ?
C3 C4 1.387(3) . ?
C3 C8 1.397(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(3) . ?
C6 C7 1.391(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.380(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(3) . ?
C9 C14 1.390(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(3) . ?
C12 C13 1.382(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(3) . ?
C15 C20 1.391(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(3) . ?
C18 C19 1.388(3) . ?
C18 C21 1.509(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(3) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?

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
C1 N1 H1 116.5(16) . . ?
C1 N1 C21 123.98(18) . 3_666 ?
C21 N1 H1 119.4(16) 3_666 . ?
C1 N2 H2 118.9(16) . . ?
C1 N2 C2 122.70(18) . . ?
C2 N2 H2 118.3(16) . . ?
C6 N3 C15 119.95(16) . . ?
C9 N3 C6 120.76(16) . . ?
C9 N3 C15 119.10(16) . . ?
O1 C1 N1 122.90(18) . . ?
O1 C1 N2 122.33(18) . . ?
N2 C1 N1 114.76(18) . . ?
N2 C2 H2A 108.8 . . ?
N2 C2 H2B 108.8 . . ?
N2 C2 C3 113.86(16) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C4 C3 C2 121.23(17) . . ?
C4 C3 C8 117.88(18) . . ?
C8 C3 C2 120.89(17) . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.41(19) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.15(19) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 N3 121.00(18) . . ?
C7 C6 N3 120.27(18) . . ?
C7 C6 C5 118.72(19) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.69(19) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 H8 119.4 . . ?
C7 C8 C3 121.13(19) . . ?
C7 C8 H8 119.4 . . ?
C10 C9 N3 120.66(19) . . ?
C14 C9 N3 120.61(19) . . ?
C14 C9 C10 118.72(19) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.2(2) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 Br1 119.92(16) . . ?
C11 C12 C13 121.17(19) . . ?
C13 C12 Br1 118.89(16) . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.12(19) . . ?
C14 C13 H13 120.4 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 120.9(2) . . ?
C13 C14 H14 119.5 . . ?
C16 C15 N3 120.28(18) . . ?
C16 C15 C20 119.10(19) . . ?
C20 C15 N3 120.62(19) . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.09(19) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.15(19) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C19 118.16(19) . . ?
C17 C18 C21 121.01(18) . . ?
C19 C18 C21 120.82(19) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.2(2) . . ?
C20 C19 H19 119.4 . . ?
C15 C20 H20 119.9 . . ?
C19 C20 C15 120.2(2) . . ?
C19 C20 H20 119.9 . . ?
N1 C21 C18 112.95(17) 3_666 . ?
N1 C21 H21A 109.0 3_666 . ?
N1 C21 H21B 109.0 3_666 . ?
C18 C21 H21A 109.0 . . ?
C18 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?

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
_geom_hbond_publ_flag
N1 H1 O1 0.820(16) 2.067(17) 2.845(2) 158(2) 1_545 yes
N2 H2 O1 0.810(16) 2.179(18) 2.915(2) 151(2) 1_545 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C12 C13 C14 176.86(16) . . . . ?
N2 C2 C3 C4 126.8(2) . . . . ?
N2 C2 C3 C8 -53.6(3) . . . . ?
N3 C6 C7 C8 -177.8(2) . . . . ?
N3 C9 C10 C11 177.6(2) . . . . ?
N3 C9 C14 C13 -177.17(19) . . . . ?
N3 C15 C16 C17 -177.04(19) . . . . ?
N3 C15 C20 C19 178.4(2) . . . . ?
C1 N2 C2 C3 100.9(2) . . . . ?
C2 N2 C1 O1 -1.6(3) . . . . ?
C2 N2 C1 N1 177.67(17) . . . . ?
C2 C3 C4 C5 -179.3(2) . . . . ?
C2 C3 C8 C7 179.8(2) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C3 C8 C7 -0.6(3) . . . . ?
C4 C5 C6 N3 178.3(2) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C5 C6 C7 C8 1.2(3) . . . . ?
C6 N3 C9 C10 39.9(3) . . . . ?
C6 N3 C9 C14 -140.4(2) . . . . ?
C6 N3 C15 C16 -144.4(2) . . . . ?
C6 N3 C15 C20 36.0(3) . . . . ?
C6 C7 C8 C3 -0.6(3) . . . . ?
C8 C3 C4 C5 1.1(3) . . . . ?
C9 N3 C6 C5 34.3(3) . . . . ?
C9 N3 C6 C7 -146.7(2) . . . . ?
C9 N3 C15 C16 40.7(3) . . . . ?
C9 N3 C15 C20 -139.0(2) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C9 C14 C13 2.5(3) . . . . ?
C10 C11 C12 Br1 -176.40(16) . . . . ?
C10 C11 C12 C13 1.9(3) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C12 C13 C14 C9 -0.8(3) . . . . ?
C14 C9 C10 C11 -2.1(3) . . . . ?
C15 N3 C6 C5 -140.6(2) . . . . ?
C15 N3 C6 C7 38.4(3) . . . . ?
C15 N3 C9 C10 -145.2(2) . . . . ?
C15 N3 C9 C14 34.5(3) . . . . ?
C15 C16 C17 C18 -1.5(3) . . . . ?
C16 C15 C20 C19 -1.2(3) . . . . ?
C16 C17 C18 C19 -0.9(3) . . . . ?
C16 C17 C18 C21 178.68(19) . . . . ?
C17 C18 C19 C20 2.2(3) . . . . ?
C17 C18 C21 N1 106.2(2) . . . 3_666 ?
C18 C19 C20 C15 -1.2(3) . . . . ?
C19 C18 C21 N1 -74.3(3) . . . 3_666 ?
C20 C15 C16 C17 2.6(3) . . . . ?
C21 N1 C1 O1 -1.4(3) 3_666 . . . ?
C21 N1 C1 N2 179.33(18) 3_666 . . . ?
C21 C18 C19 C20 -177.3(2) . . . . ?

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

data_brnph3dmc_bz
_database_code_depnum_ccdc_archive 'CCDC 1899529'
loop_
_audit_author_name
_audit_author_address
'Mark D Smith'
;University of South Carolina
United States of America
;
_audit_update_record             
;
2019-02-25 deposited with the CCDC.	2019-04-18 downloaded from the CCDC.
;
_audit_creation_date             2018-12-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H36 Br2 N6 O2, 0.56(C6 H6)'
_chemical_formula_sum            'C45.38 H39.38 Br2 N6 O2'
_chemical_formula_weight         860.52
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.8777(5)
_cell_length_b                   4.6345(2)
_cell_length_c                   26.7173(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.975(2)
_cell_angle_gamma                90
_cell_volume                     1936.28(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7032
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.000
_cell_measurement_theta_min      2.189
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.585
_exptl_absorpt_coefficient_mu    2.141
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.7270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1285 before and 0.0577 after correction.
The Ratio of minimum to maximum transmission is 0.8434.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             879
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            22892
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.074
_diffrn_reflns_theta_max         25.074
_diffrn_reflns_theta_min         1.842
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2771
_reflns_number_total             3428
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0381P)²+2.8319P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0944
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N1-H1 = N2-H2
 0.85 with sigma of 0.02
 C2S-C1S = C3S-C2S = C3S-C1S_$2 = C2S_$2-C1S_$2 = C3S_$2-C2S_$2 = C3S_$2-C1S =
 C6S_$3-C5S_$3 = C6S_$3-C4S = C5S-C4S = C6S-C5S = C6S-C4S_$3 = C5S_$3-C4S_$3
 1.4 with sigma of 0.015
 H5S-H8
 -2.1 with sigma of 0.02
 C6S_$3-C6S \\sim C5S-C5S_$3 \\sim C4S_$3-C4S
 with sigma of 0.015
3. Restrained planarity
 C5S_$3, C4S_$3, C6S, C5S, C4S, C6S_$3
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uiso(C4S) = Uiso(C5S) = Uiso(C6S)
5. Others
 Sof(C4S)=Sof(H4S)=Sof(C5S)=Sof(H5S)=Sof(C6S)=Sof(H6S)=1-FVAR(1)
 Sof(C1S)=Sof(H1S)=Sof(C2S)=Sof(H2S)=Sof(C3S)=Sof(H3S)=0.5*FVAR(2)
6.a Riding coordinates:
 C1S(H1S), C2S(H2S), C3S(H3S)
6.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C21(H21A,H21B)
6.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C4S(H4S), C5S(H5S), C6S(H6S)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.17727(2) 0.86530(9) 0.72092(2) 0.03819(14) Uani 1 1 d . . . . .
O1 O 0.59997(13) 0.8856(5) 0.33811(9) 0.0293(5) Uani 1 1 d . . . . .
N1 N 0.53251(16) 0.4564(6) 0.32047(10) 0.0216(6) Uani 1 1 d D . . . .
H1 H 0.535(2) 0.279(4) 0.3223(12) 0.023(9) Uiso 1 1 d D . . . .
N2 N 0.67184(16) 0.4667(6) 0.35954(10) 0.0197(6) Uani 1 1 d D . . . .
H2 H 0.671(2) 0.290(4) 0.3592(12) 0.019(9) Uiso 1 1 d D . . . .
N3 N 0.82384(16) 0.6711(6) 0.59609(10) 0.0295(7) Uani 1 1 d . . . . .
C1 C 0.60112(17) 0.6199(7) 0.33935(10) 0.0175(6) Uani 1 1 d . . . . .
C2 C 0.75336(18) 0.6042(7) 0.37831(11) 0.0236(7) Uani 1 1 d . . . . .
H2A H 0.752933 0.800404 0.363611 0.028 Uiso 1 1 calc R . . . .
H2B H 0.799237 0.493188 0.366256 0.028 Uiso 1 1 calc R . . . .
C3 C 0.77413(18) 0.6272(7) 0.43547(11) 0.0223(7) Uani 1 1 d . . . . .
C4 C 0.8482(2) 0.5158(8) 0.46303(12) 0.0296(8) Uani 1 1 d . . . . .
H4 H 0.888192 0.424254 0.445579 0.035 Uiso 1 1 calc R . . . .
C5 C 0.8661(2) 0.5334(8) 0.51568(12) 0.0327(8) Uani 1 1 d . . . . .
H5 H 0.918139 0.456456 0.533651 0.039 Uiso 1 1 calc R . . . .
C6 C 0.80863(19) 0.6626(7) 0.54211(11) 0.0243(7) Uani 1 1 d . . . . .
C7 C 0.7344(2) 0.7770(9) 0.51522(14) 0.0399(9) Uani 1 1 d . . . . .
H7 H 0.694741 0.869667 0.532759 0.048 Uiso 1 1 calc R . . . .
C8 C 0.7172(2) 0.7578(9) 0.46270(14) 0.0414(10) Uani 1 1 d . . . . .
H8 H 0.665218 0.835551 0.444797 0.050 Uiso 1 1 calc DR . . . .
C9 C 0.90752(19) 0.7073(7) 0.62377(11) 0.0239(7) Uani 1 1 d . . . . .
C10 C 0.9645(2) 0.8956(8) 0.60709(13) 0.0349(8) Uani 1 1 d . . . . .
H10 H 0.947755 0.996168 0.575978 0.042 Uiso 1 1 calc R . . . .
C11 C 1.0455(2) 0.9396(8) 0.63508(12) 0.0361(9) Uani 1 1 d . . . . .
H11 H 1.084078 1.069096 0.623226 0.043 Uiso 1 1 calc R . . . .
C12 C 1.0695(2) 0.7943(7) 0.68011(12) 0.0261(7) Uani 1 1 d . . . . .
C13 C 1.0148(2) 0.5992(8) 0.69680(12) 0.0301(8) Uani 1 1 d . . . . .
H13 H 1.032183 0.495800 0.727548 0.036 Uiso 1 1 calc R . . . .
C14 C 0.9346(2) 0.5558(8) 0.66847(12) 0.0302(8) Uani 1 1 d . . . . .
H14 H 0.897214 0.419734 0.679735 0.036 Uiso 1 1 calc R . . . .
C15 C 0.7547(2) 0.6142(8) 0.62268(12) 0.0283(7) Uani 1 1 d . . . . .
C16 C 0.74795(19) 0.7638(9) 0.66648(12) 0.0317(8) Uani 1 1 d . . . . .
H16 H 0.788625 0.908606 0.678813 0.038 Uiso 1 1 calc R . . . .
C17 C 0.68156(19) 0.7021(8) 0.69250(12) 0.0299(8) Uani 1 1 d . . . . .
H17 H 0.677925 0.805299 0.722768 0.036 Uiso 1 1 calc R . . . .
C18 C 0.62097(19) 0.4960(7) 0.67571(12) 0.0248(7) Uani 1 1 d . . . . .
C19 C 0.6271(3) 0.3547(9) 0.63120(17) 0.0564(13) Uani 1 1 d . . . . .
H19 H 0.585168 0.215152 0.618219 0.068 Uiso 1 1 calc R . . . .
C20 C 0.6933(3) 0.4116(9) 0.60487(17) 0.0569(13) Uani 1 1 d . . . . .
H20 H 0.696227 0.310175 0.574330 0.068 Uiso 1 1 calc R . . . .
C21 C 0.54903(18) 0.4263(7) 0.70391(11) 0.0246(7) Uani 1 1 d . . . . .
H21A H 0.543911 0.214126 0.706469 0.029 Uiso 1 1 calc R . . . .
H21B H 0.563158 0.504286 0.738858 0.029 Uiso 1 1 calc R . . . .
C1S C 0.5115(5) 0.066(2) 0.4514(4) 0.054(3) Uani 0.437(5) 1 d D . P A 1
H1S H 0.517529 0.112362 0.417116 0.065 Uiso 0.437(5) 1 d R . P A 1
C2S C 0.5110(7) 0.286(3) 0.4865(4) 0.059(3) Uani 0.437(5) 1 d D . P A 1
H2S H 0.521895 0.479643 0.477626 0.071 Uiso 0.437(5) 1 d R . P A 1
C3S C 0.4991(7) 0.219(2) 0.5354(4) 0.058(3) Uani 0.437(5) 1 d D . P A 1
H3S H 0.494658 0.371325 0.559200 0.070 Uiso 0.437(5) 1 d R . P A 1
C4S C 0.5557(13) 0.485(4) 0.4651(8) 0.041(8) Uiso 0.126(9) 1 d D . P A 2
H4S H 0.593654 0.475318 0.441332 0.049 Uiso 0.126(9) 1 calc R . P A 2
C5S C 0.5331(14) 0.753(2) 0.4831(10) 0.041(8) Uiso 0.126(9) 1 d D . P A 2
H5S H 0.555811 0.925747 0.471540 0.049 Uiso 0.126(9) 1 calc DR . P A 2
C6S C 0.4777(17) 0.768(2) 0.5179(11) 0.041(8) Uiso 0.126(9) 1 d D . P A 2
H6S H 0.462417 0.949478 0.530053 0.049 Uiso 0.126(9) 1 calc R . P A 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 C12 1.892(3) . ?
O1 C1 1.232(4) . ?
N1 H1 0.824(18) . ?
N1 C1 1.351(4) . ?
N1 C21 1.451(4) 3_666 ?
N2 H2 0.817(18) . ?
N2 C1 1.359(4) . ?
N2 C2 1.452(4) . ?
N3 C6 1.421(4) . ?
N3 C9 1.414(4) . ?
N3 C15 1.432(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.509(4) . ?
C3 C4 1.376(4) . ?
C3 C8 1.393(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(4) . ?
C6 C7 1.376(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.385(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(5) . ?
C9 C14 1.388(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.374(5) . ?
C12 C13 1.381(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.378(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(5) . ?
C15 C20 1.378(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.374(5) . ?
C18 C19 1.376(5) . ?
C18 C21 1.508(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(5) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C1S H1S 0.9602 . ?
C1S C2S 1.385(9) . ?
C1S C3S 1.387(9) 3_656 ?
C2S H2S 0.9502 . ?
C2S C3S 1.390(9) . ?
C3S H3S 0.9599 . ?
C4S H4S 0.9500 . ?
C4S C5S 1.403(11) . ?
C4S C6S 1.392(11) 3_666 ?
C5S H5S 0.9500 . ?
C5S C6S 1.387(11) . ?
C6S H6S 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
C1 N1 H1 121(2) . . ?
C1 N1 C21 123.8(3) . 3_666 ?
C21 N1 H1 115(2) 3_666 . ?
C1 N2 H2 120(2) . . ?
C1 N2 C2 122.3(3) . . ?
C2 N2 H2 117(2) . . ?
C6 N3 C15 119.2(3) . . ?
C9 N3 C6 120.9(2) . . ?
C9 N3 C15 119.6(2) . . ?
O1 C1 N1 122.9(3) . . ?
O1 C1 N2 122.7(3) . . ?
N1 C1 N2 114.4(3) . . ?
N2 C2 H2A 108.8 . . ?
N2 C2 H2B 108.8 . . ?
N2 C2 C3 113.9(2) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C4 C3 C2 122.1(3) . . ?
C4 C3 C8 117.1(3) . . ?
C8 C3 C2 120.7(3) . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.7(3) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 N3 121.3(3) . . ?
C7 C6 N3 119.9(3) . . ?
C7 C6 C5 118.8(3) . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.3(3) . . ?
C8 C7 H7 119.8 . . ?
C3 C8 H8 119.2 . . ?
C7 C8 C3 121.7(3) . . ?
C7 C8 H8 119.2 . . ?
C10 C9 N3 120.9(3) . . ?
C10 C9 C14 118.3(3) . . ?
C14 C9 N3 120.9(3) . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.1(3) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(3) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 Br1 120.4(3) . . ?
C11 C12 C13 120.6(3) . . ?
C13 C12 Br1 119.0(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.4(3) . . ?
C14 C13 H13 120.3 . . ?
C9 C14 H14 119.4 . . ?
C13 C14 C9 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C16 C15 N3 120.5(3) . . ?
C20 C15 N3 120.8(3) . . ?
C20 C15 C16 118.7(3) . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.9(3) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.0 . . ?
C18 C17 C16 121.9(3) . . ?
C18 C17 H17 119.0 . . ?
C17 C18 C19 117.5(3) . . ?
C17 C18 C21 122.2(3) . . ?
C19 C18 C21 120.2(3) . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.4(4) . . ?
C20 C19 H19 119.3 . . ?
C15 C20 C19 120.5(4) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
N1 C21 C18 112.9(3) 3_666 . ?
N1 C21 H21A 109.0 3_666 . ?
N1 C21 H21B 109.0 3_666 . ?
C18 C21 H21A 109.0 . . ?
C18 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C2S C1S H1S 119.7 . . ?
C2S C1S C3S 120.9(9) . 3_656 ?
C3S C1S H1S 119.4 3_656 . ?
C1S C2S H2S 120.2 . . ?
C1S C2S C3S 119.4(10) . . ?
C3S C2S H2S 120.4 . . ?
C1S C3S C2S 119.7(10) 3_656 . ?
C1S C3S H3S 120.5 3_656 . ?
C2S C3S H3S 119.7 . . ?
C5S C4S H4S 120.0 . . ?
C6S C4S H4S 120.0 3_666 . ?
C6S C4S C5S 119.9(5) 3_666 . ?
C4S C5S H5S 120.0 . . ?
C6S C5S C4S 120.1(5) . . ?
C6S C5S H5S 120.0 . . ?
C4S C6S H6S 120.0 3_666 . ?
C5S C6S H6S 120.0 . . ?

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
_geom_hbond_publ_flag
N1 H1 O1 0.824(18) 2.10(2) 2.862(3) 153(3) 1_545 yes
N2 H2 O1 0.817(18) 2.21(2) 2.942(4) 149(3) 1_545 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C12 C13 C14 177.1(3) . . . . ?
N2 C2 C3 C4 124.0(3) . . . . ?
N2 C2 C3 C8 -54.4(4) . . . . ?
N3 C6 C7 C8 -177.0(4) . . . . ?
N3 C9 C10 C11 177.6(3) . . . . ?
N3 C9 C14 C13 -177.2(3) . . . . ?
N3 C15 C16 C17 -178.6(3) . . . . ?
N3 C15 C20 C19 179.1(4) . . . . ?
C1 N2 C2 C3 102.6(3) . . . . ?
C2 N2 C1 O1 -4.1(4) . . . . ?
C2 N2 C1 N1 175.5(3) . . . . ?
C2 C3 C4 C5 -178.9(3) . . . . ?
C2 C3 C8 C7 179.0(4) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C4 C3 C8 C7 0.5(6) . . . . ?
C4 C5 C6 N3 177.0(3) . . . . ?
C4 C5 C6 C7 -1.1(6) . . . . ?
C5 C6 C7 C8 1.2(6) . . . . ?
C6 N3 C9 C10 39.7(5) . . . . ?
C6 N3 C9 C14 -140.6(3) . . . . ?
C6 N3 C15 C16 -143.2(3) . . . . ?
C6 N3 C15 C20 36.2(5) . . . . ?
C6 C7 C8 C3 -0.9(6) . . . . ?
C8 C3 C4 C5 -0.4(5) . . . . ?
C9 N3 C6 C5 36.3(5) . . . . ?
C9 N3 C6 C7 -145.6(3) . . . . ?
C9 N3 C15 C16 42.8(5) . . . . ?
C9 N3 C15 C20 -137.8(4) . . . . ?
C9 C10 C11 C12 -0.1(6) . . . . ?
C10 C9 C14 C13 2.6(5) . . . . ?
C10 C11 C12 Br1 -176.6(3) . . . . ?
C10 C11 C12 C13 2.0(5) . . . . ?
C11 C12 C13 C14 -1.5(5) . . . . ?
C12 C13 C14 C9 -0.8(5) . . . . ?
C14 C9 C10 C11 -2.1(5) . . . . ?
C15 N3 C6 C5 -137.6(3) . . . . ?
C15 N3 C6 C7 40.5(5) . . . . ?
C15 N3 C9 C10 -146.5(3) . . . . ?
C15 N3 C9 C14 33.3(5) . . . . ?
C15 C16 C17 C18 -0.6(5) . . . . ?
C16 C15 C20 C19 -1.5(7) . . . . ?
C16 C17 C18 C19 -1.3(5) . . . . ?
C16 C17 C18 C21 179.6(3) . . . . ?
C17 C18 C19 C20 1.8(7) . . . . ?
C17 C18 C21 N1 104.7(4) . . . 3_666 ?
C18 C19 C20 C15 -0.4(8) . . . . ?
C19 C18 C21 N1 -74.4(4) . . . 3_666 ?
C20 C15 C16 C17 2.0(5) . . . . ?
C21 N1 C1 O1 1.1(4) 3_666 . . . ?
C21 N1 C1 N2 -178.5(3) 3_666 . . . ?
C21 C18 C19 C20 -179.1(4) . . . . ?
C1S C2S C3S C1S 0.5(18) . . . 3_656 ?
C3S C1S C2S C3S -0.5(18) 3_656 . . . ?
C4S C5S C6S C4S -0.01(17) . . . 3_666 ?
C6S C4S C5S C6S 0.01(17) 3_666 . . . ?

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

data_brnph3dmc_br
_database_code_depnum_ccdc_archive 'CCDC 1899532'
loop_
_audit_author_name
_audit_author_address
'Mark D Smith'
;University of South Carolina
United States of America
;
_audit_update_record             
;
2019-02-25 deposited with the CCDC.	2019-04-18 downloaded from the CCDC.
;
_audit_creation_date             2018-11-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H36 Br2 N6 O2, 0.52(C6 H5 Br)'
_chemical_formula_sum            'C45.09 H38.58 Br2.52 N6 O2'
_chemical_formula_weight         897.51
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.8509(6)
_cell_length_b                   4.6392(2)
_cell_length_c                   26.7433(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.019(2)
_cell_angle_gamma                90
_cell_volume                     1936.59(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3967
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.197
_cell_measurement_theta_min      2.190
_shelx_estimated_absorpt_T_max   0.924
_shelx_estimated_absorpt_T_min   0.740
_exptl_absorpt_coefficient_mu    2.672
_exptl_absorpt_correction_T_max  0.6191
_exptl_absorpt_correction_T_min  0.5122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0742 before and 0.0568 after correction.
The Ratio of minimum to maximum transmission is 0.8273.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             910
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16210
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.305
_diffrn_reflns_theta_max         24.305
_diffrn_reflns_theta_min         1.305
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2323
_reflns_number_total             3149
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3149
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0408P)²+4.9166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1081
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N1-H1 = N2-H2
 0.85 with sigma of 0.02
 Br1S-C1S
 1.9 with sigma of 0.015
 C7S-Br2S
 1.9 with sigma of 0.015
 C8S-Br2S \\sim C12S-Br2S
 with sigma of 0.01
 C2S-Br1S \\sim C6S-Br1S
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uiso(C1S) = Uiso(C7S) = Uiso(C6S) = Uiso(C12S) = Uiso(C11S) = Uiso(C10S) =
Uiso(C5S) = Uiso(C4S) = Uiso(C9S) = Uiso(C8S) = Uiso(C3S) = Uiso(C2S)
4. Others
 Sof(C7S)=Sof(C8S)=Sof(H8S)=Sof(C9S)=Sof(H9S)=Sof(C10S)=Sof(H10S)=Sof(C11S)=
 Sof(H11S)=Sof(C12S)=Sof(H12S)=Sof(Br2S)=FVAR(1)
 Sof(C1S)=Sof(C2S)=Sof(H2S)=Sof(C3S)=Sof(H3S)=Sof(C4S)=Sof(H4S)=Sof(C5S)=
 Sof(H5S)=Sof(C6S)=Sof(H6S)=Sof(Br1S)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C21(H21A,H21B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C2S(H2S), C3S(H3S), C4S(H4S), C5S(H5S),
  C6S(H6S), C8S(H8S), C9S(H9S), C10S(H10S), C11S(H11S), C12S(H12S)
5.c Fitted hexagon refined as free rotating group:
 C1S(C2S,C3S,C4S,C5S,C6S), C7S(C8S,C9S,C10S,C11S,C12S)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.17755(3) 0.87146(12) 0.72133(2) 0.03215(18) Uani 1 1 d . . . . .
O1 O 0.60034(18) 0.8777(7) 0.33825(11) 0.0239(7) Uani 1 1 d . . . . .
N1 N 0.5326(2) 0.4475(8) 0.32003(14) 0.0196(9) Uani 1 1 d D . . . .
H1 H 0.538(3) 0.269(5) 0.3238(18) 0.027(14) Uiso 1 1 d D . . . .
N2 N 0.6723(2) 0.4596(8) 0.35937(14) 0.0173(8) Uani 1 1 d D . . . .
H2 H 0.670(3) 0.283(4) 0.3566(18) 0.022(14) Uiso 1 1 d D . . . .
N3 N 0.8240(2) 0.6727(9) 0.59603(13) 0.0243(9) Uani 1 1 d . . . . .
C1 C 0.6016(3) 0.6105(10) 0.33904(15) 0.0170(10) Uani 1 1 d . . . . .
C2 C 0.7538(3) 0.5970(10) 0.37818(16) 0.0210(10) Uani 1 1 d . . . . .
H2A H 0.753314 0.792979 0.363484 0.025 Uiso 1 1 calc R . . . .
H2B H 0.799779 0.486289 0.366118 0.025 Uiso 1 1 calc R . . . .
C3 C 0.7750(2) 0.6204(10) 0.43550(15) 0.0171(9) Uani 1 1 d . . . . .
C4 C 0.8496(3) 0.5102(10) 0.46313(17) 0.0230(11) Uani 1 1 d . . . . .
H4 H 0.889654 0.418202 0.445831 0.028 Uiso 1 1 calc R . . . .
C5 C 0.8674(3) 0.5309(11) 0.51589(17) 0.0250(11) Uani 1 1 d . . . . .
H5 H 0.919542 0.455500 0.534052 0.030 Uiso 1 1 calc R . . . .
C6 C 0.8092(3) 0.6613(10) 0.54208(16) 0.0208(10) Uani 1 1 d . . . . .
C7 C 0.7351(3) 0.7776(11) 0.51443(17) 0.0265(12) Uani 1 1 d . . . . .
H7 H 0.695394 0.872576 0.531607 0.032 Uiso 1 1 calc R . . . .
C8 C 0.7184(3) 0.7574(10) 0.46237(17) 0.0256(11) Uani 1 1 d . . . . .
H8 H 0.667093 0.838610 0.444216 0.031 Uiso 1 1 calc R . . . .
C9 C 0.9078(3) 0.7102(10) 0.62379(16) 0.0209(11) Uani 1 1 d . . . . .
C10 C 0.9650(3) 0.8980(11) 0.60676(17) 0.0298(11) Uani 1 1 d . . . . .
H10 H 0.948692 0.996545 0.575437 0.036 Uiso 1 1 calc R . . . .
C11 C 1.0454(3) 0.9420(11) 0.63504(17) 0.0290(12) Uani 1 1 d . . . . .
H11 H 1.084033 1.071581 0.623306 0.035 Uiso 1 1 calc R . . . .
C12 C 1.0696(3) 0.7979(10) 0.68040(16) 0.0211(11) Uani 1 1 d . . . . .
C13 C 1.0151(3) 0.6039(11) 0.69677(16) 0.0243(11) Uani 1 1 d . . . . .
H13 H 1.032600 0.500629 0.727500 0.029 Uiso 1 1 calc R . . . .
C14 C 0.9347(3) 0.5590(10) 0.66847(17) 0.0253(12) Uani 1 1 d . . . . .
H14 H 0.897342 0.422828 0.679721 0.030 Uiso 1 1 calc R . . . .
C15 C 0.7552(3) 0.6183(10) 0.62238(16) 0.0209(10) Uani 1 1 d . . . . .
C16 C 0.7483(3) 0.7712(11) 0.66584(17) 0.0257(11) Uani 1 1 d . . . . .
H16 H 0.788823 0.917398 0.677752 0.031 Uiso 1 1 calc R . . . .
C17 C 0.6816(3) 0.7102(11) 0.69225(17) 0.0245(11) Uani 1 1 d . . . . .
H17 H 0.678208 0.814043 0.722460 0.029 Uiso 1 1 calc R . . . .
C18 C 0.6207(3) 0.5042(10) 0.67571(16) 0.0186(10) Uani 1 1 d . . . . .
C19 C 0.6284(4) 0.3593(12) 0.6317(2) 0.0417(14) Uani 1 1 d . . . . .
H19 H 0.587036 0.216768 0.619245 0.050 Uiso 1 1 calc R . . . .
C20 C 0.6940(4) 0.4135(12) 0.6051(2) 0.0413(14) Uani 1 1 d . . . . .
H20 H 0.696934 0.309368 0.574908 0.050 Uiso 1 1 calc R . . . .
C21 C 0.5494(3) 0.4372(10) 0.70386(16) 0.0219(11) Uani 1 1 d . . . . .
H21A H 0.544375 0.225328 0.706726 0.026 Uiso 1 1 calc R . . . .
H21B H 0.563960 0.516280 0.738678 0.026 Uiso 1 1 calc R . . . .
C1S C 0.5011(18) 0.552(3) 0.5009(7) 0.032(3) Uiso 0.187(2) 1 d D . P A -1
C2S C 0.4860(15) 0.379(3) 0.5408(6) 0.032(3) Uiso 0.187(2) 1 d DG . P A -1
H2S H 0.473544 0.464400 0.570988 0.038 Uiso 0.187(2) 1 calc R . P A -1
C3S C 0.4890(19) 0.080(3) 0.5367(7) 0.032(3) Uiso 0.187(2) 1 d G . P A -1
H3S H 0.478698 -0.037809 0.563956 0.038 Uiso 0.187(2) 1 calc R . P A -1
C4S C 0.507(2) -0.045(3) 0.4925(8) 0.032(3) Uiso 0.187(2) 1 d G . P A -1
H4S H 0.509298 -0.248797 0.489669 0.038 Uiso 0.187(2) 1 calc R . P A -1
C5S C 0.5223(17) 0.128(3) 0.4526(7) 0.032(3) Uiso 0.187(2) 1 d G . P A -1
H5S H 0.534745 0.042422 0.422413 0.038 Uiso 0.187(2) 1 calc R . P A -1
C6S C 0.5193(16) 0.426(3) 0.4567(7) 0.032(3) Uiso 0.187(2) 1 d DG . P A -1
H6S H 0.529592 0.544632 0.429444 0.038 Uiso 0.187(2) 1 calc R . P A -1
Br1S Br 0.496(3) 0.960(4) 0.5065(12) 0.083(7) Uani 0.187(2) 1 d D . P A -1
C7S C 0.494(4) 0.344(4) 0.5206(11) 0.032(3) Uiso 0.071(2) 1 d D . P B -2
C8S C 0.482(4) 0.095(4) 0.5477(15) 0.032(3) Uiso 0.071(2) 1 d DG . P B -2
H8S H 0.469843 0.108975 0.581035 0.038 Uiso 0.071(2) 1 calc R . P B -2
C9S C 0.490(5) -0.173(4) 0.5258(19) 0.032(3) Uiso 0.071(2) 1 d G . P B -2
H9S H 0.482053 -0.343563 0.544314 0.038 Uiso 0.071(2) 1 calc R . P B -2
C10S C 0.508(4) -0.193(6) 0.4770(19) 0.032(3) Uiso 0.071(2) 1 d G . P B -2
H10S H 0.513011 -0.376983 0.462090 0.038 Uiso 0.071(2) 1 calc R . P B -2
C11S C 0.519(4) 0.056(7) 0.4500(15) 0.032(3) Uiso 0.071(2) 1 d G . P B -2
H11S H 0.531759 0.042135 0.416588 0.038 Uiso 0.071(2) 1 calc R . P B -2
C12S C 0.512(4) 0.325(6) 0.4718(12) 0.032(3) Uiso 0.071(2) 1 d DG . P B -2
H12S H 0.519548 0.494677 0.453308 0.038 Uiso 0.071(2) 1 calc R . P B -2
Br2S Br 0.4802(9) 0.713(3) 0.5497(4) 0.070(4) Uani 0.071(2) 1 d D . P B -2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.895(4) . ?
O1 C1 1.240(5) . ?
N1 H1 0.837(19) . ?
N1 C1 1.353(6) . ?
N1 C21 1.448(5) 3_666 ?
N2 H2 0.82(2) . ?
N2 C1 1.353(6) . ?
N2 C2 1.450(5) . ?
N3 C6 1.422(5) . ?
N3 C9 1.414(5) . ?
N3 C15 1.421(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.515(6) . ?
C3 C4 1.378(6) . ?
C3 C8 1.396(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(6) . ?
C6 C7 1.383(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.374(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(7) . ?
C9 C14 1.387(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.378(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(6) . ?
C12 C13 1.371(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(6) . ?
C15 C20 1.379(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.399(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.375(6) . ?
C18 C19 1.379(7) . ?
C18 C21 1.496(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.381(7) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C1S C2S 1.3900 . ?
C1S C6S 1.3900 . ?
C1S Br1S 1.901(15) . ?
C2S H2S 0.9500 . ?
C2S C3S 1.3900 . ?
C3S H3S 0.9500 . ?
C3S C4S 1.3900 . ?
C4S H4S 0.9500 . ?
C4S C5S 1.3900 . ?
C5S H5S 0.9500 . ?
C5S C6S 1.3900 . ?
C6S H6S 0.9500 . ?
C7S C8S 1.3900 . ?
C7S C12S 1.3900 . ?
C7S Br2S 1.906(15) . ?
C8S H8S 0.9500 . ?
C8S C9S 1.3900 . ?
C9S H9S 0.9500 . ?
C9S C10S 1.3900 . ?
C10S H10S 0.9500 . ?
C10S C11S 1.3900 . ?
C11S H11S 0.9500 . ?
C11S C12S 1.3900 . ?
C12S H12S 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
C1 N1 H1 117(3) . . ?
C1 N1 C21 124.3(4) . 3_666 ?
C21 N1 H1 119(3) 3_666 . ?
C1 N2 H2 117(3) . . ?
C1 N2 C2 122.6(4) . . ?
C2 N2 H2 119(3) . . ?
C9 N3 C6 120.8(3) . . ?
C9 N3 C15 119.6(3) . . ?
C15 N3 C6 119.4(3) . . ?
O1 C1 N1 122.9(4) . . ?
O1 C1 N2 122.3(4) . . ?
N2 C1 N1 114.9(4) . . ?
N2 C2 H2A 108.7 . . ?
N2 C2 H2B 108.7 . . ?
N2 C2 C3 114.2(3) . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C4 C3 C2 122.3(4) . . ?
C4 C3 C8 117.4(4) . . ?
C8 C3 C2 120.3(4) . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.4(4) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 N3 121.3(4) . . ?
C7 C6 N3 120.2(4) . . ?
C7 C6 C5 118.4(4) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.7(4) . . ?
C8 C7 H7 119.6 . . ?
C3 C8 H8 119.2 . . ?
C7 C8 C3 121.7(4) . . ?
C7 C8 H8 119.2 . . ?
C10 C9 N3 120.8(4) . . ?
C14 C9 N3 120.7(4) . . ?
C14 C9 C10 118.6(4) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(4) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(4) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 Br1 120.4(3) . . ?
C13 C12 Br1 119.3(3) . . ?
C13 C12 C11 120.3(4) . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(4) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.8(4) . . ?
C13 C14 H14 119.6 . . ?
C16 C15 N3 120.3(4) . . ?
C20 C15 N3 120.9(4) . . ?
C20 C15 C16 118.8(4) . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.8(4) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.9(4) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 C19 116.9(4) . . ?
C17 C18 C21 122.1(4) . . ?
C19 C18 C21 121.0(4) . . ?
C18 C19 H19 118.8 . . ?
C18 C19 C20 122.5(5) . . ?
C20 C19 H19 118.8 . . ?
C15 C20 C19 120.1(5) . . ?
C15 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
N1 C21 C18 113.6(4) 3_666 . ?
N1 C21 H21A 108.8 3_666 . ?
N1 C21 H21B 108.8 3_666 . ?
C18 C21 H21A 108.8 . . ?
C18 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C2S C1S C6S 120.0 . . ?
C2S C1S Br1S 120.0(4) . . ?
C6S C1S Br1S 120.0(4) . . ?
C1S C2S H2S 120.0 . . ?
C3S C2S C1S 120.0 . . ?
C3S C2S H2S 120.0 . . ?
C2S C3S H3S 120.0 . . ?
C2S C3S C4S 120.0 . . ?
C4S C3S H3S 120.0 . . ?
C3S C4S H4S 120.0 . . ?
C5S C4S C3S 120.0 . . ?
C5S C4S H4S 120.0 . . ?
C4S C5S H5S 120.0 . . ?
C4S C5S C6S 120.0 . . ?
C6S C5S H5S 120.0 . . ?
C1S C6S H6S 120.0 . . ?
C5S C6S C1S 120.0 . . ?
C5S C6S H6S 120.0 . . ?
C8S C7S C12S 120.0 . . ?
C8S C7S Br2S 120.0(4) . . ?
C12S C7S Br2S 119.9(4) . . ?
C7S C8S H8S 120.0 . . ?
C7S C8S C9S 120.0 . . ?
C9S C8S H8S 120.0 . . ?
C8S C9S H9S 120.0 . . ?
C8S C9S C10S 120.0 . . ?
C10S C9S H9S 120.0 . . ?
C9S C10S H10S 120.0 . . ?
C11S C10S C9S 120.0 . . ?
C11S C10S H10S 120.0 . . ?
C10S C11S H11S 120.0 . . ?
C12S C11S C10S 120.0 . . ?
C12S C11S H11S 120.0 . . ?
C7S C12S H12S 120.0 . . ?
C11S C12S C7S 120.0 . . ?
C11S C12S H12S 120.0 . . ?

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
_geom_hbond_publ_flag
N1 H1 O1 0.837(19) 2.07(3) 2.863(5) 158(5) 1_545 yes
N2 H2 O1 0.82(2) 2.19(3) 2.947(5) 152(4) 1_545 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C12 C13 C14 176.9(3) . . . . ?
N2 C2 C3 C4 124.2(5) . . . . ?
N2 C2 C3 C8 -55.9(6) . . . . ?
N3 C6 C7 C8 -177.3(5) . . . . ?
N3 C9 C10 C11 177.4(4) . . . . ?
N3 C9 C14 C13 -177.3(4) . . . . ?
N3 C15 C16 C17 -178.2(4) . . . . ?
N3 C15 C20 C19 178.7(5) . . . . ?
C1 N2 C2 C3 102.9(5) . . . . ?
C2 N2 C1 O1 -4.9(6) . . . . ?
C2 N2 C1 N1 175.4(4) . . . . ?
C2 C3 C4 C5 -179.2(4) . . . . ?
C2 C3 C8 C7 178.8(4) . . . . ?
C3 C4 C5 C6 0.8(7) . . . . ?
C4 C3 C8 C7 -1.2(7) . . . . ?
C4 C5 C6 N3 177.0(4) . . . . ?
C4 C5 C6 C7 -2.2(7) . . . . ?
C5 C6 C7 C8 1.8(7) . . . . ?
C6 N3 C9 C10 39.7(6) . . . . ?
C6 N3 C9 C14 -140.0(5) . . . . ?
C6 N3 C15 C16 -143.1(5) . . . . ?
C6 N3 C15 C20 36.7(7) . . . . ?
C6 C7 C8 C3 -0.1(8) . . . . ?
C8 C3 C4 C5 0.9(7) . . . . ?
C9 N3 C6 C5 36.1(7) . . . . ?
C9 N3 C6 C7 -144.8(5) . . . . ?
C9 N3 C15 C16 42.9(6) . . . . ?
C9 N3 C15 C20 -137.3(5) . . . . ?
C9 C10 C11 C12 0.4(7) . . . . ?
C10 C9 C14 C13 3.1(7) . . . . ?
C10 C11 C12 Br1 -176.7(4) . . . . ?
C10 C11 C12 C13 2.1(7) . . . . ?
C11 C12 C13 C14 -1.9(7) . . . . ?
C12 C13 C14 C9 -0.7(7) . . . . ?
C14 C9 C10 C11 -2.9(7) . . . . ?
C15 N3 C6 C5 -137.8(5) . . . . ?
C15 N3 C6 C7 41.3(6) . . . . ?
C15 N3 C9 C10 -146.4(5) . . . . ?
C15 N3 C9 C14 33.9(6) . . . . ?
C15 C16 C17 C18 -1.3(7) . . . . ?
C16 C15 C20 C19 -1.4(8) . . . . ?
C16 C17 C18 C19 0.1(7) . . . . ?
C16 C17 C18 C21 179.8(4) . . . . ?
C17 C18 C19 C20 0.5(8) . . . . ?
C17 C18 C21 N1 104.8(5) . . . 3_666 ?
C18 C19 C20 C15 0.2(9) . . . . ?
C19 C18 C21 N1 -75.5(6) . . . 3_666 ?
C20 C15 C16 C17 1.9(7) . . . . ?
C21 N1 C1 O1 0.9(7) 3_666 . . . ?
C21 N1 C1 N2 -179.4(4) 3_666 . . . ?
C21 C18 C19 C20 -179.2(5) . . . . ?
C1S C2S C3S C4S 0.0 . . . . ?
C2S C1S C6S C5S 0.0 . . . . ?
C2S C3S C4S C5S 0.0 . . . . ?
C3S C4S C5S C6S 0.0 . . . . ?
C4S C5S C6S C1S 0.0 . . . . ?
C6S C1S C2S C3S 0.0 . . . . ?
Br1S C1S C2S C3S 180(3) . . . . ?
Br1S C1S C6S C5S -180(3) . . . . ?
C7S C8S C9S C10S 0.0 . . . . ?
C8S C7S C12S C11S 0.0 . . . . ?
C8S C9S C10S C11S 0.0 . . . . ?
C9S C10S C11S C12S 0.0 . . . . ?
C10S C11S C12S C7S 0.0 . . . . ?
C12S C7S C8S C9S 0.0 . . . . ?
Br2S C7S C8S C9S 178(4) . . . . ?
Br2S C7S C12S C11S -178(4) . . . . ?

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

data_brnph3dmc_f
_database_code_depnum_ccdc_archive 'CCDC 1899530'
loop_
_audit_author_name
_audit_author_address
'Mark D Smith'
;University of South Carolina
United States of America
;
_audit_update_record             
;
2019-02-25 deposited with the CCDC.	2019-04-18 downloaded from the CCDC.
;
_audit_creation_date             2018-10-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H36 Br2 N6 O2, 0.5(C6 H5 F)'
_chemical_formula_sum            'C45 H38.50 Br2 F0.50 N6 O2'
_chemical_formula_weight         864.64
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.8857(6)
_cell_length_b                   4.6310(2)
_cell_length_c                   26.7350(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.910(2)
_cell_angle_gamma                90
_cell_volume                     1937.46(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5706
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.995
_cell_measurement_theta_min      2.186
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.754
_exptl_absorpt_coefficient_mu    2.142
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0676 before and 0.0507 after correction.
The Ratio of minimum to maximum transmission is 0.8584.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             882
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            19628
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.049
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_min         2.186
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2688
_reflns_number_total             3422
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.088
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3422
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²+5.8328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1163
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F1S-C1S
 1.4 with sigma of 0.01
 N1-H1 = N2-H2
 0.85 with sigma of 0.02
 F1S-C2S \\sim F1S-C6S
 with sigma of 0.01
 C2S-F1S \\sim C6S-F1S
 with sigma of 0.01
3. Others
 Fixed Sof: F1S(0.25) C1S(0.25) C2S(0.25) H2S(0.25) C3S(0.25) H3S(0.25)
 C4S(0.25) H4S(0.25) C5S(0.25) H5S(0.25) C6S(0.25) H6S(0.25)
4.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C21(H21A,H21B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C2S(H2S), C3S(H3S), C4S(H4S), C5S(H5S),
  C6S(H6S)
4.c Fitted hexagon refined as free rotating group:
 C1S(C2S,C3S,C4S,C5S,C6S)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.17678(3) 0.85544(12) 0.72070(2) 0.03971(17) Uani 1 1 d . . . . .
O1 O 0.60025(17) 0.9007(6) 0.33812(12) 0.0315(7) Uani 1 1 d . . . . .
N1 N 0.5323(2) 0.4702(8) 0.32052(13) 0.0233(7) Uani 1 1 d D . . . .
H1 H 0.538(3) 0.291(4) 0.3213(16) 0.024(12) Uiso 1 1 d D . . . .
N2 N 0.67223(19) 0.4806(8) 0.35903(13) 0.0212(7) Uani 1 1 d D . . . .
H2 H 0.670(3) 0.302(4) 0.3576(16) 0.026(13) Uiso 1 1 d D . . . .
N3 N 0.8233(2) 0.6606(9) 0.59622(13) 0.0316(8) Uani 1 1 d . . . . .
C1 C 0.6015(2) 0.6322(9) 0.33908(13) 0.0176(8) Uani 1 1 d . . . . .
C2 C 0.7536(2) 0.6167(9) 0.37858(14) 0.0244(9) Uani 1 1 d . . . . .
H2A H 0.753190 0.815178 0.364772 0.029 Uiso 1 1 calc R . . . .
H2B H 0.799539 0.508303 0.366130 0.029 Uiso 1 1 calc R . . . .
C3 C 0.7741(2) 0.6319(9) 0.43570(14) 0.0232(8) Uani 1 1 d . . . . .
C4 C 0.8474(3) 0.5185(11) 0.46288(16) 0.0323(10) Uani 1 1 d . . . . .
H4 H 0.887437 0.429329 0.445148 0.039 Uiso 1 1 calc R . . . .
C5 C 0.8654(3) 0.5294(11) 0.51563(16) 0.0344(11) Uani 1 1 d . . . . .
H5 H 0.917163 0.449414 0.533308 0.041 Uiso 1 1 calc R . . . .
C6 C 0.8081(2) 0.6562(10) 0.54234(15) 0.0271(9) Uani 1 1 d . . . . .
C7 C 0.7344(3) 0.7746(11) 0.51546(18) 0.0401(12) Uani 1 1 d . . . . .
H7 H 0.694670 0.865753 0.533131 0.048 Uiso 1 1 calc R . . . .
C8 C 0.7176(3) 0.7619(11) 0.46292(18) 0.0416(12) Uani 1 1 d . . . . .
H8 H 0.666288 0.844100 0.445147 0.050 Uiso 1 1 calc R . . . .
C9 C 0.9070(2) 0.6985(9) 0.62390(15) 0.0255(9) Uani 1 1 d . . . . .
C10 C 0.9640(3) 0.8885(11) 0.60740(17) 0.0384(11) Uani 1 1 d . . . . .
H10 H 0.947236 0.991336 0.576546 0.046 Uiso 1 1 calc R . . . .
C11 C 1.0446(3) 0.9302(11) 0.63519(17) 0.0397(12) Uani 1 1 d . . . . .
H11 H 1.083192 1.059754 0.623362 0.048 Uiso 1 1 calc R . . . .
C12 C 1.0689(3) 0.7838(10) 0.68000(15) 0.0288(10) Uani 1 1 d . . . . .
C13 C 1.0142(2) 0.5893(10) 0.69660(17) 0.0329(11) Uani 1 1 d . . . . .
H13 H 1.031619 0.485272 0.727269 0.039 Uiso 1 1 calc R . . . .
C14 C 0.9339(2) 0.5466(11) 0.66831(16) 0.0329(11) Uani 1 1 d . . . . .
H14 H 0.896396 0.410624 0.679554 0.039 Uiso 1 1 calc R . . . .
C15 C 0.7546(2) 0.6032(9) 0.62283(16) 0.0281(9) Uani 1 1 d . . . . .
C16 C 0.7473(2) 0.7505(11) 0.66655(16) 0.0329(11) Uani 1 1 d . . . . .
H16 H 0.788001 0.895168 0.678922 0.039 Uiso 1 1 calc R . . . .
C17 C 0.6812(2) 0.6902(11) 0.69280(16) 0.0324(11) Uani 1 1 d . . . . .
H17 H 0.677443 0.793926 0.722998 0.039 Uiso 1 1 calc R . . . .
C18 C 0.6208(2) 0.4821(9) 0.67574(15) 0.0260(9) Uani 1 1 d . . . . .
C19 C 0.6272(4) 0.3428(13) 0.6313(2) 0.0612(17) Uani 1 1 d . . . . .
H19 H 0.585108 0.204478 0.617989 0.073 Uiso 1 1 calc R . . . .
C20 C 0.6938(4) 0.3993(12) 0.6053(2) 0.0632(18) Uani 1 1 d . . . . .
H20 H 0.697405 0.295975 0.575013 0.076 Uiso 1 1 calc R . . . .
C21 C 0.5490(2) 0.4112(9) 0.70398(14) 0.0245(9) Uani 1 1 d . . . . .
H21A H 0.543849 0.198835 0.706383 0.029 Uiso 1 1 calc R . . . .
H21B H 0.563054 0.488639 0.738945 0.029 Uiso 1 1 calc R . . . .
F1S F 0.4858(12) 0.354(3) 0.5147(5) 0.099(5) Uiso 0.25 1 d D . P A -1
C1S C 0.4937(10) 0.6389(19) 0.5053(4) 0.041(5) Uiso 0.25 1 d D . P A -1
C2S C 0.4834(8) 0.839(2) 0.5425(3) 0.034(4) Uiso 0.25 1 d DG . P A -1
H2S H 0.471054 0.775985 0.574218 0.040 Uiso 0.25 1 calc R . P A -1
C3S C 0.4910(9) 1.133(2) 0.5331(4) 0.044(5) Uiso 0.25 1 d G . P A -1
H3S H 0.483923 1.269739 0.558534 0.053 Uiso 0.25 1 calc R . P A -1
C4S C 0.5090(10) 1.2255(19) 0.4867(5) 0.037(4) Uiso 0.25 1 d G . P A -1
H4S H 0.514218 1.425949 0.480305 0.044 Uiso 0.25 1 calc R . P A -1
C5S C 0.5193(10) 1.025(2) 0.4495(4) 0.068(7) Uiso 0.25 1 d G . P A -1
H5S H 0.531645 1.088405 0.417759 0.081 Uiso 0.25 1 calc R . P A -1
C6S C 0.5117(11) 0.732(2) 0.4588(4) 0.069(7) Uiso 0.25 1 d DG . P A -1
H6S H 0.518776 0.594648 0.433442 0.083 Uiso 0.25 1 calc R . P A -1


_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 C12 1.894(4) . ?
O1 C1 1.244(5) . ?
N1 H1 0.834(19) . ?
N1 C1 1.352(5) . ?
N1 C21 1.453(5) 3_666 ?
N2 H2 0.828(19) . ?
N2 C1 1.354(5) . ?
N2 C2 1.452(5) . ?
N3 C6 1.419(5) . ?
N3 C9 1.417(5) . ?
N3 C15 1.427(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.507(5) . ?
C3 C4 1.368(5) . ?
C3 C8 1.386(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(6) . ?
C6 C7 1.378(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.385(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(6) . ?
C9 C14 1.383(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.373(6) . ?
C12 C13 1.377(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(6) . ?
C15 C20 1.374(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(6) . ?
C18 C19 1.372(7) . ?
C18 C21 1.508(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(7) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
F1S C1S 1.354(9) . ?
C1S C2S 1.3900 . ?
C1S C6S 1.3900 . ?
C2S H2S 0.9500 . ?
C2S C3S 1.3900 . ?
C3S H3S 0.9500 . ?
C3S C4S 1.3900 . ?
C4S H4S 0.9500 . ?
C4S C5S 1.3900 . ?
C5S H5S 0.9500 . ?
C5S C6S 1.3900 . ?
C6S H6S 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
C1 N1 H1 117(3) . . ?
C1 N1 C21 124.0(3) . 3_666 ?
C21 N1 H1 118(3) 3_666 . ?
C1 N2 H2 118(3) . . ?
C1 N2 C2 122.9(4) . . ?
C2 N2 H2 118(3) . . ?
C6 N3 C15 119.5(3) . . ?
C9 N3 C6 120.8(3) . . ?
C9 N3 C15 119.5(3) . . ?
O1 C1 N1 122.6(3) . . ?
O1 C1 N2 122.4(3) . . ?
N1 C1 N2 115.1(4) . . ?
N2 C2 H2A 108.7 . . ?
N2 C2 H2B 108.7 . . ?
N2 C2 C3 114.1(3) . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C4 C3 C2 122.4(4) . . ?
C4 C3 C8 117.2(4) . . ?
C8 C3 C2 120.4(3) . . ?
C3 C4 H4 118.9 . . ?
C3 C4 C5 122.2(4) . . ?
C5 C4 H4 118.9 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.1(4) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 N3 121.2(4) . . ?
C7 C6 N3 120.3(4) . . ?
C7 C6 C5 118.4(4) . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.7(4) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 H8 119.3 . . ?
C7 C8 C3 121.5(4) . . ?
C7 C8 H8 119.3 . . ?
C10 C9 N3 121.1(4) . . ?
C14 C9 N3 120.6(4) . . ?
C14 C9 C10 118.3(4) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.9(4) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(4) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 Br1 120.4(3) . . ?
C11 C12 C13 120.4(4) . . ?
C13 C12 Br1 119.2(3) . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.5(4) . . ?
C14 C13 H13 120.3 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.1(4) . . ?
C13 C14 H14 119.5 . . ?
C16 C15 N3 121.0(4) . . ?
C20 C15 N3 120.7(4) . . ?
C20 C15 C16 118.3(4) . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.8(4) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.1(4) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C21 121.9(4) . . ?
C19 C18 C17 117.6(4) . . ?
C19 C18 C21 120.5(4) . . ?
C18 C19 H19 119.2 . . ?
C18 C19 C20 121.5(5) . . ?
C20 C19 H19 119.2 . . ?
C15 C20 C19 120.7(5) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
N1 C21 C18 112.5(3) 3_666 . ?
N1 C21 H21A 109.1 3_666 . ?
N1 C21 H21B 109.1 3_666 . ?
C18 C21 H21A 109.1 . . ?
C18 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
F1S C1S C2S 119.5(4) . . ?
F1S C1S C6S 120.5(4) . . ?
C2S C1S C6S 120.0 . . ?
C1S C2S H2S 120.0 . . ?
C3S C2S C1S 120.0 . . ?
C3S C2S H2S 120.0 . . ?
C2S C3S H3S 120.0 . . ?
C4S C3S C2S 120.0 . . ?
C4S C3S H3S 120.0 . . ?
C3S C4S H4S 120.0 . . ?
C3S C4S C5S 120.0 . . ?
C5S C4S H4S 120.0 . . ?
C4S C5S H5S 120.0 . . ?
C6S C5S C4S 120.0 . . ?
C6S C5S H5S 120.0 . . ?
C1S C6S H6S 120.0 . . ?
C5S C6S C1S 120.0 . . ?
C5S C6S H6S 120.0 . . ?

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
_geom_hbond_publ_flag
N1 H1 O1 0.834(19) 2.07(2) 2.858(4) 157(4) 1_545 yes
N2 H2 O1 0.828(19) 2.18(3) 2.935(4) 151(4) 1_545 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C12 C13 C14 176.8(3) . . . . ?
N2 C2 C3 C4 123.9(4) . . . . ?
N2 C2 C3 C8 -55.6(6) . . . . ?
N3 C6 C7 C8 -177.7(5) . . . . ?
N3 C9 C10 C11 178.3(4) . . . . ?
N3 C9 C14 C13 -177.7(4) . . . . ?
N3 C15 C16 C17 -178.8(4) . . . . ?
N3 C15 C20 C19 179.7(5) . . . . ?
C1 N2 C2 C3 103.0(4) . . . . ?
C2 N2 C1 O1 -3.2(6) . . . . ?
C2 N2 C1 N1 177.1(3) . . . . ?
C2 C3 C4 C5 -179.0(4) . . . . ?
C2 C3 C8 C7 179.0(5) . . . . ?
C3 C4 C5 C6 0.4(7) . . . . ?
C4 C3 C8 C7 -0.5(7) . . . . ?
C4 C5 C6 N3 177.6(4) . . . . ?
C4 C5 C6 C7 -1.1(7) . . . . ?
C5 C6 C7 C8 1.1(7) . . . . ?
C6 N3 C9 C10 38.9(6) . . . . ?
C6 N3 C9 C14 -141.3(4) . . . . ?
C6 N3 C15 C16 -142.5(4) . . . . ?
C6 N3 C15 C20 37.4(7) . . . . ?
C6 C7 C8 C3 -0.3(8) . . . . ?
C8 C3 C4 C5 0.4(7) . . . . ?
C9 N3 C6 C5 37.1(6) . . . . ?
C9 N3 C6 C7 -144.2(4) . . . . ?
C9 N3 C15 C16 42.5(6) . . . . ?
C9 N3 C15 C20 -137.7(5) . . . . ?
C9 C10 C11 C12 -0.5(7) . . . . ?
C10 C9 C14 C13 2.2(7) . . . . ?
C10 C11 C12 Br1 -176.2(4) . . . . ?
C10 C11 C12 C13 1.9(7) . . . . ?
C11 C12 C13 C14 -1.3(7) . . . . ?
C12 C13 C14 C9 -0.8(7) . . . . ?
C14 C9 C10 C11 -1.5(7) . . . . ?
C15 N3 C6 C5 -137.9(4) . . . . ?
C15 N3 C6 C7 40.8(6) . . . . ?
C15 N3 C9 C10 -146.2(4) . . . . ?
C15 N3 C9 C14 33.6(6) . . . . ?
C15 C16 C17 C18 -0.3(7) . . . . ?
C16 C15 C20 C19 -0.4(9) . . . . ?
C16 C17 C18 C19 -1.7(7) . . . . ?
C16 C17 C18 C21 179.4(4) . . . . ?
C17 C18 C19 C20 2.6(9) . . . . ?
C17 C18 C21 N1 104.5(4) . . . 3_666 ?
C18 C19 C20 C15 -1.6(10) . . . . ?
C19 C18 C21 N1 -74.4(6) . . . 3_666 ?
C20 C15 C16 C17 1.3(7) . . . . ?
C21 N1 C1 O1 2.4(6) 3_666 . . . ?
C21 N1 C1 N2 -177.9(3) 3_666 . . . ?
C21 C18 C19 C20 -178.4(5) . . . . ?
F1S C1S C2S C3S -179.7(12) . . . . ?
F1S C1S C6S C5S 179.7(13) . . . . ?
C1S C2S C3S C4S 0.0 . . . . ?
C2S C1S C6S C5S 0.0 . . . . ?
C2S C3S C4S C5S 0.0 . . . . ?
C3S C4S C5S C6S 0.0 . . . . ?
C4S C5S C6S C1S 0.0 . . . . ?
C6S C1S C2S C3S 0.0 . . . . ?

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

data_brnph3dmc_cl
_database_code_depnum_ccdc_archive 'CCDC 1899531'
loop_
_audit_author_name
_audit_author_address
'Mark D Smith'
;University of South Carolina
United States of America
;
_audit_update_record             
;
2019-02-25 deposited with the CCDC.	2019-04-18 downloaded from the CCDC.
;
_audit_creation_date             2018-11-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H36 Br2 N6 O2, 0.52(C6 H5 Cl)'
_chemical_formula_sum            'C45.14 H38.61 Br2 Cl0.52 N6 O2'
_chemical_formula_weight         875.54
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.8533(6)
_cell_length_b                   4.6332(2)
_cell_length_c                   26.7661(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.069(2)
_cell_angle_gamma                90
_cell_volume                     1935.73(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4828
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.962
_cell_measurement_theta_min      2.610
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.812
_exptl_absorpt_coefficient_mu    2.178
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0629 before and 0.0543 after correction.
The Ratio of minimum to maximum transmission is 0.9023.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             893
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            18624
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.050
_diffrn_reflns_theta_max         25.052
_diffrn_reflns_theta_min         1.840
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2724
_reflns_number_total             3419
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3419
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0393P)²+3.2935P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0982
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 N1-H1 = N2-H2
 0.85 with sigma of 0.02
 Cl1S-C1S
 1.74 with sigma of 0.015
 C7S-Cl2S
 1.74 with sigma of 0.015
 H8S-H19
 -2 with sigma of 0.02
 C8S-Cl2S \\sim C12S-Cl2S
 with sigma of 0.01
 C2S-Cl1S \\sim C6S-Cl1S
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uiso(C1S) = Uiso(C7S) = Uiso(C6S) = Uiso(C12S) = Uiso(C11S) = Uiso(C10S) =
Uiso(C5S) = Uiso(C4S) = Uiso(C9S) = Uiso(C8S) = Uiso(C3S) = Uiso(C2S)
4. Others
 Sof(C7S)=Sof(C8S)=Sof(H8S)=Sof(C9S)=Sof(H9S)=Sof(C10S)=Sof(H10S)=Sof(C11S)=
 Sof(H11S)=Sof(C12S)=Sof(H12S)=Sof(Cl2S)=FVAR(1)
 Sof(C1S)=Sof(C2S)=Sof(H2S)=Sof(C3S)=Sof(H3S)=Sof(C4S)=Sof(H4S)=Sof(C5S)=
 Sof(H5S)=Sof(C6S)=Sof(H6S)=Sof(Cl1S)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C21(H21A,H21B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C2S(H2S), C3S(H3S), C4S(H4S), C5S(H5S),
  C6S(H6S), C8S(H8S), C9S(H9S), C10S(H10S), C11S(H11S), C12S(H12S)
5.c Fitted hexagon refined as free rotating group:
 C1S(C2S,C3S,C4S,C5S,C6S), C7S(C8S,C9S,C10S,C11S,C12S)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.17739(2) 0.86637(9) 0.72124(2) 0.03123(14) Uani 1 1 d . . . . .
O1 O 0.60052(15) 0.8846(5) 0.33808(9) 0.0243(6) Uani 1 1 d . . . . .
N1 N 0.53264(18) 0.4538(6) 0.31991(11) 0.0188(6) Uani 1 1 d D . . . .
H1 H 0.540(2) 0.276(4) 0.3235(14) 0.023 Uiso 1 1 d DR . . . .
N2 N 0.67254(17) 0.4659(6) 0.35920(11) 0.0167(6) Uani 1 1 d D . . . .
H2 H 0.669(2) 0.287(4) 0.3583(14) 0.020 Uiso 1 1 d DR . . . .
N3 N 0.82369(18) 0.6692(7) 0.59599(10) 0.0252(7) Uani 1 1 d . . . . .
C1 C 0.6020(2) 0.6161(7) 0.33905(11) 0.0155(7) Uani 1 1 d . . . . .
C2 C 0.7541(2) 0.6032(8) 0.37854(12) 0.0193(7) Uani 1 1 d . . . . .
H2A H 0.753849 0.799558 0.363937 0.023 Uiso 1 1 calc R . . . .
H2B H 0.800233 0.492336 0.366736 0.023 Uiso 1 1 calc R . . . .
C3 C 0.7744(2) 0.6261(8) 0.43543(12) 0.0168(7) Uani 1 1 d . . . . .
C4 C 0.8492(2) 0.5137(8) 0.46303(13) 0.0225(8) Uani 1 1 d . . . . .
H4 H 0.889392 0.423054 0.445675 0.027 Uiso 1 1 calc R . . . .
C5 C 0.8665(2) 0.5310(8) 0.51568(13) 0.0244(8) Uani 1 1 d . . . . .
H5 H 0.918508 0.454073 0.533770 0.029 Uiso 1 1 calc R . . . .
C6 C 0.8086(2) 0.6595(8) 0.54202(13) 0.0214(8) Uani 1 1 d . . . . .
C7 C 0.7344(2) 0.7779(8) 0.51456(13) 0.0246(8) Uani 1 1 d . . . . .
H7 H 0.694681 0.871898 0.531832 0.030 Uiso 1 1 calc R . . . .
C8 C 0.7179(2) 0.7601(8) 0.46223(14) 0.0252(8) Uani 1 1 d . . . . .
H8 H 0.666588 0.841661 0.444124 0.030 Uiso 1 1 calc R . . . .
C9 C 0.9073(2) 0.7067(7) 0.62378(12) 0.0191(8) Uani 1 1 d . . . . .
C10 C 0.9647(3) 0.8955(8) 0.60700(14) 0.0298(9) Uani 1 1 d . . . . .
H10 H 0.948282 0.995043 0.575789 0.036 Uiso 1 1 calc R . . . .
C11 C 1.0451(3) 0.9393(8) 0.63522(14) 0.0307(9) Uani 1 1 d . . . . .
H11 H 1.083686 1.069516 0.623597 0.037 Uiso 1 1 calc R . . . .
C12 C 1.0691(2) 0.7945(8) 0.68009(12) 0.0204(8) Uani 1 1 d . . . . .
C13 C 1.0148(2) 0.5983(8) 0.69678(13) 0.0244(8) Uani 1 1 d . . . . .
H13 H 1.032603 0.494493 0.727417 0.029 Uiso 1 1 calc R . . . .
C14 C 0.9343(2) 0.5542(8) 0.66860(13) 0.0252(9) Uani 1 1 d . . . . .
H14 H 0.896892 0.418295 0.679863 0.030 Uiso 1 1 calc R . . . .
C15 C 0.7546(2) 0.6145(8) 0.62246(13) 0.0216(8) Uani 1 1 d . . . . .
C16 C 0.7478(2) 0.7652(9) 0.66598(14) 0.0269(9) Uani 1 1 d . . . . .
H16 H 0.788498 0.910929 0.678028 0.032 Uiso 1 1 calc R . . . .
C17 C 0.6815(2) 0.7044(8) 0.69237(13) 0.0246(9) Uani 1 1 d . . . . .
H17 H 0.678347 0.807355 0.722684 0.029 Uiso 1 1 calc R . . . .
C18 C 0.6206(2) 0.4994(8) 0.67559(12) 0.0189(7) Uani 1 1 d . . . . .
C19 C 0.6275(3) 0.3543(10) 0.63141(16) 0.0414(11) Uani 1 1 d . . . . .
H19 H 0.585898 0.212497 0.618822 0.050 Uiso 1 1 calc DR . . . .
C20 C 0.6933(3) 0.4098(9) 0.60502(16) 0.0413(11) Uani 1 1 d . . . . .
H20 H 0.696281 0.306445 0.574724 0.050 Uiso 1 1 calc R . . . .
C21 C 0.5492(2) 0.4301(8) 0.70412(12) 0.0197(8) Uani 1 1 d . . . . .
H21A H 0.544248 0.217886 0.706859 0.024 Uiso 1 1 calc R . . . .
H21B H 0.563827 0.508929 0.738940 0.024 Uiso 1 1 calc R . . . .
C1S C 0.4996(13) 0.5621(19) 0.5014(5) 0.036(3) Uiso 0.187(3) 1 d D . P A -1
C2S C 0.4860(11) 0.379(2) 0.5404(4) 0.036(3) Uiso 0.187(3) 1 d DG . P A -1
H2S H 0.472932 0.457195 0.570995 0.043 Uiso 0.187(3) 1 calc R . P A -1
C3S C 0.4914(13) 0.082(2) 0.5346(5) 0.036(3) Uiso 0.187(3) 1 d G . P A -1
H3S H 0.482093 -0.043128 0.561274 0.043 Uiso 0.187(3) 1 calc R . P A -1
C4S C 0.5105(16) -0.032(2) 0.4899(6) 0.036(3) Uiso 0.187(3) 1 d G . P A -1
H4S H 0.514171 -0.235403 0.485950 0.043 Uiso 0.187(3) 1 calc R . P A -1
C5S C 0.5241(14) 0.151(2) 0.4509(5) 0.036(3) Uiso 0.187(3) 1 d G . P A -1
H5S H 0.537088 0.072643 0.420345 0.043 Uiso 0.187(3) 1 calc R . P A -1
C6S C 0.5186(12) 0.448(2) 0.4567(4) 0.036(3) Uiso 0.187(3) 1 d DG . P A -1
H6S H 0.527929 0.572968 0.430065 0.043 Uiso 0.187(3) 1 calc R . P A -1
Cl1S Cl 0.4993(8) 0.927(2) 0.5100(3) 0.065(4) Uani 0.187(3) 1 d D . P A -1
C7S C 0.491(2) 0.372(4) 0.5232(8) 0.036(3) Uiso 0.074(3) 1 d D . P B -2
C8S C 0.4783(12) 0.129(5) 0.5514(9) 0.036(3) Uiso 0.074(3) 1 d DG . P B -2
H8S H 0.465023 0.150088 0.584475 0.043 Uiso 0.074(3) 1 calc DR . P B -2
C9S C 0.485(3) -0.144(4) 0.5312(14) 0.036(3) Uiso 0.074(3) 1 d G . P B -2
H9S H 0.476512 -0.310679 0.550499 0.043 Uiso 0.074(3) 1 calc R . P B -2
C10S C 0.505(3) -0.175(5) 0.4828(15) 0.036(3) Uiso 0.074(3) 1 d G . P B -2
H10S H 0.509227 -0.362094 0.469036 0.043 Uiso 0.074(3) 1 calc R . P B -2
C11S C 0.517(3) 0.068(6) 0.4546(12) 0.036(3) Uiso 0.074(3) 1 d G . P B -2
H11S H 0.530453 0.047257 0.421548 0.043 Uiso 0.074(3) 1 calc R . P B -2
C12S C 0.510(3) 0.342(5) 0.4748(9) 0.036(3) Uiso 0.074(3) 1 d DG . P B -2
H12S H 0.518964 0.508027 0.455522 0.043 Uiso 0.074(3) 1 calc R . P B -2
Cl2S Cl 0.4835(16) 0.717(4) 0.5492(8) 0.077(8) Uani 0.074(3) 1 d D . P B -2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.900(3) . ?
O1 C1 1.245(4) . ?
N1 H1 0.834(19) . ?
N1 C1 1.356(4) . ?
N1 C21 1.447(4) 3_666 ?
N2 H2 0.830(19) . ?
N2 C1 1.347(4) . ?
N2 C2 1.452(4) . ?
N3 C6 1.423(4) . ?
N3 C9 1.413(4) . ?
N3 C15 1.427(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.504(4) . ?
C3 C4 1.384(5) . ?
C3 C8 1.388(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(5) . ?
C6 C7 1.386(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(5) . ?
C9 C14 1.394(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.378(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.370(5) . ?
C12 C13 1.380(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.378(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(5) . ?
C15 C20 1.380(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.395(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.373(5) . ?
C18 C19 1.381(5) . ?
C18 C21 1.507(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.382(6) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C1S C2S 1.3900 . ?
C1S C6S 1.3900 . ?
C1S Cl1S 1.705(12) . ?
C2S H2S 0.9500 . ?
C2S C3S 1.3900 . ?
C3S H3S 0.9500 . ?
C3S C4S 1.3900 . ?
C4S H4S 0.9500 . ?
C4S C5S 1.3900 . ?
C5S H5S 0.9500 . ?
C5S C6S 1.3900 . ?
C6S H6S 0.9500 . ?
C7S C8S 1.3900 . ?
C7S C12S 1.3900 . ?
C7S Cl2S 1.754(15) . ?
C8S H8S 0.9500 . ?
C8S C9S 1.3900 . ?
C9S H9S 0.9500 . ?
C9S C10S 1.3900 . ?
C10S H10S 0.9500 . ?
C10S C11S 1.3900 . ?
C11S H11S 0.9500 . ?
C11S C12S 1.3900 . ?
C12S H12S 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
C1 N1 H1 115(3) . . ?
C1 N1 C21 124.5(3) . 3_666 ?
C21 N1 H1 121(3) 3_666 . ?
C1 N2 H2 117(3) . . ?
C1 N2 C2 122.8(3) . . ?
C2 N2 H2 120(3) . . ?
C6 N3 C15 119.4(3) . . ?
C9 N3 C6 121.0(3) . . ?
C9 N3 C15 119.4(3) . . ?
O1 C1 N1 122.3(3) . . ?
O1 C1 N2 122.4(3) . . ?
N2 C1 N1 115.2(3) . . ?
N2 C2 H2A 108.7 . . ?
N2 C2 H2B 108.7 . . ?
N2 C2 C3 114.3(3) . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 C8 117.5(3) . . ?
C8 C3 C2 120.8(3) . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 N3 121.4(3) . . ?
C5 C6 C7 118.4(3) . . ?
C7 C6 N3 120.2(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.4(3) . . ?
C8 C7 H7 119.8 . . ?
C3 C8 H8 119.1 . . ?
C7 C8 C3 121.7(3) . . ?
C7 C8 H8 119.1 . . ?
C10 C9 N3 120.9(3) . . ?
C10 C9 C14 118.4(3) . . ?
C14 C9 N3 120.7(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 Br1 120.5(3) . . ?
C11 C12 C13 120.8(3) . . ?
C13 C12 Br1 118.7(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.4(3) . . ?
C14 C13 H13 120.3 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.8(3) . . ?
C13 C14 H14 119.6 . . ?
C16 C15 N3 120.6(3) . . ?
C16 C15 C20 118.7(3) . . ?
C20 C15 N3 120.7(3) . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.6(3) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C19 117.4(3) . . ?
C17 C18 C21 122.0(3) . . ?
C19 C18 C21 120.6(3) . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 121.8(4) . . ?
C20 C19 H19 119.1 . . ?
C15 C20 C19 120.3(4) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
N1 C21 C18 113.0(3) 3_666 . ?
N1 C21 H21A 109.0 3_666 . ?
N1 C21 H21B 109.0 3_666 . ?
C18 C21 H21A 109.0 . . ?
C18 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C2S C1S C6S 120.0 . . ?
C2S C1S Cl1S 120.0(4) . . ?
C6S C1S Cl1S 119.9(4) . . ?
C1S C2S H2S 120.0 . . ?
C1S C2S C3S 120.0 . . ?
C3S C2S H2S 120.0 . . ?
C2S C3S H3S 120.0 . . ?
C2S C3S C4S 120.0 . . ?
C4S C3S H3S 120.0 . . ?
C3S C4S H4S 120.0 . . ?
C5S C4S C3S 120.0 . . ?
C5S C4S H4S 120.0 . . ?
C4S C5S H5S 120.0 . . ?
C4S C5S C6S 120.0 . . ?
C6S C5S H5S 120.0 . . ?
C1S C6S H6S 120.0 . . ?
C5S C6S C1S 120.0 . . ?
C5S C6S H6S 120.0 . . ?
C8S C7S C12S 120.0 . . ?
C8S C7S Cl2S 119.8(4) . . ?
C12S C7S Cl2S 120.2(4) . . ?
C7S C8S H8S 120.0 . . ?
C7S C8S C9S 120.0 . . ?
C9S C8S H8S 120.0 . . ?
C8S C9S H9S 120.0 . . ?
C8S C9S C10S 120.0 . . ?
C10S C9S H9S 120.0 . . ?
C9S C10S H10S 120.0 . . ?
C11S C10S C9S 120.0 . . ?
C11S C10S H10S 120.0 . . ?
C10S C11S H11S 120.0 . . ?
C10S C11S C12S 120.0 . . ?
C12S C11S H11S 120.0 . . ?
C7S C12S H12S 120.0 . . ?
C11S C12S C7S 120.0 . . ?
C11S C12S H12S 120.0 . . ?

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
_geom_hbond_publ_flag
N1 H1 O1 0.834(19) 2.06(2) 2.858(4) 160(4) 1_545 yes
N2 H2 O1 0.830(19) 2.18(2) 2.941(4) 153(3) 1_545 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C12 C13 C14 176.8(3) . . . . ?
N2 C2 C3 C4 124.1(4) . . . . ?
N2 C2 C3 C8 -55.4(5) . . . . ?
N3 C6 C7 C8 -177.7(4) . . . . ?
N3 C9 C10 C11 177.6(3) . . . . ?
N3 C9 C14 C13 -177.6(3) . . . . ?
N3 C15 C16 C17 -178.2(3) . . . . ?
N3 C15 C20 C19 178.8(4) . . . . ?
C1 N2 C2 C3 102.2(4) . . . . ?
C2 N2 C1 O1 -4.0(5) . . . . ?
C2 N2 C1 N1 176.1(3) . . . . ?
C2 C3 C4 C5 -178.7(3) . . . . ?
C2 C3 C8 C7 178.5(3) . . . . ?
C3 C4 C5 C6 0.6(6) . . . . ?
C4 C3 C8 C7 -1.0(6) . . . . ?
C4 C5 C6 N3 177.5(4) . . . . ?
C4 C5 C6 C7 -2.0(6) . . . . ?
C5 C6 C7 C8 1.8(6) . . . . ?
C6 N3 C9 C10 39.5(5) . . . . ?
C6 N3 C9 C14 -140.3(4) . . . . ?
C6 N3 C15 C16 -143.1(4) . . . . ?
C6 N3 C15 C20 36.9(5) . . . . ?
C6 C7 C8 C3 -0.3(6) . . . . ?
C8 C3 C4 C5 0.8(6) . . . . ?
C9 N3 C6 C5 36.1(5) . . . . ?
C9 N3 C6 C7 -144.4(4) . . . . ?
C9 N3 C15 C16 42.5(5) . . . . ?
C9 N3 C15 C20 -137.5(4) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C10 C9 C14 C13 2.7(5) . . . . ?
C10 C11 C12 Br1 -176.8(3) . . . . ?
C10 C11 C12 C13 1.9(6) . . . . ?
C11 C12 C13 C14 -1.9(5) . . . . ?
C12 C13 C14 C9 -0.4(5) . . . . ?
C14 C9 C10 C11 -2.7(6) . . . . ?
C15 N3 C6 C5 -138.2(4) . . . . ?
C15 N3 C6 C7 41.3(5) . . . . ?
C15 N3 C9 C10 -146.2(4) . . . . ?
C15 N3 C9 C14 34.1(5) . . . . ?
C15 C16 C17 C18 -1.3(6) . . . . ?
C16 C15 C20 C19 -1.2(6) . . . . ?
C16 C17 C18 C19 0.1(6) . . . . ?
C16 C17 C18 C21 179.4(3) . . . . ?
C17 C18 C19 C20 0.5(6) . . . . ?
C17 C18 C21 N1 105.3(4) . . . 3_666 ?
C18 C19 C20 C15 0.0(7) . . . . ?
C19 C18 C21 N1 -75.4(4) . . . 3_666 ?
C20 C15 C16 C17 1.8(6) . . . . ?
C21 N1 C1 O1 1.0(5) 3_666 . . . ?
C21 N1 C1 N2 -179.0(3) 3_666 . . . ?
C21 C18 C19 C20 -178.8(4) . . . . ?
C1S C2S C3S C4S 0.0 . . . . ?
C2S C1S C6S C5S 0.0 . . . . ?
C2S C3S C4S C5S 0.0 . . . . ?
C3S C4S C5S C6S 0.0 . . . . ?
C4S C5S C6S C1S 0.0 . . . . ?
C6S C1S C2S C3S 0.0 . . . . ?
Cl1S C1S C2S C3S -176.0(18) . . . . ?
Cl1S C1S C6S C5S 176.0(18) . . . . ?
C7S C8S C9S C10S 0.0 . . . . ?
C8S C7S C12S C11S 0.0 . . . . ?
C8S C9S C10S C11S 0.0 . . . . ?
C9S C10S C11S C12S 0.0 . . . . ?
C10S C11S C12S C7S 0.0 . . . . ?
C12S C7S C8S C9S 0.0 . . . . ?
Cl2S C7S C8S C9S -179(3) . . . . ?
Cl2S C7S C12S C11S 179(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
