# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_sa4820a
_audit_block_doi                 10.5517/ccdc.csd.cc1ls23k
_database_code_depnum_ccdc_archive 'CCDC 1482888'
_audit_update_record             
;
2016-06-01 deposited with the CCDC.	2021-03-03 downloaded from the CCDC.
;
_audit_creation_date             2016-06-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H27 Br N4 O'
_chemical_formula_sum            'C23 H27 Br N4 O'
_chemical_formula_weight         455.39
_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      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                   11.5777(16)
_cell_length_b                   12.8278(18)
_cell_length_c                   15.3442(19)
_cell_angle_alpha                77.929(5)
_cell_angle_beta                 76.867(5)
_cell_angle_gamma                88.501(5)
_cell_volume                     2169.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6233
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4819
_cell_measurement_theta_min      2.3505
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.916
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.528
_exptl_crystal_size_mid          0.436
_exptl_crystal_size_min          0.206
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18414
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         1.906
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 40.0747
	          2theta: -19.7214
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 40.0747
	          2theta: -19.7214
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             9767
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0636
_diffrn_orient_matrix_UB_12      0.0271
_diffrn_orient_matrix_UB_13      0.0556
_diffrn_orient_matrix_UB_21      -0.0561
_diffrn_orient_matrix_UB_22      -0.0366
_diffrn_orient_matrix_UB_23      -0.0434
_diffrn_orient_matrix_UB_31      0.0286
_diffrn_orient_matrix_UB_32      -0.0524
_diffrn_orient_matrix_UB_33      0.0335
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8202
_reflns_number_total             9763
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     531
_refine_ls_number_reflns         9763
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.089
_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)+(0.0383P)²+1.7669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1122
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C12(H12), C6A(H6A), C12A(H12A)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B),
  C7A(H7AA,H7AB), C8A(H8AA,H8AB), C9A(H9AA,H9AB), C10A(H10C,H10D), C11A(H11C,
 H11D), C13A(H13C,H13D), C14A(H14C,H14D), C15A(H15C,H15D), C16A(H16C,H16D),
 C17A(H17C,H17D)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C22(H22), C23(H23), C19A(H19A), C20A(H20A), C22A(H22A),
 C23A(H23A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.94658(3) 0.34930(3) 0.02628(2) 0.04558(10) Uani 1 1 d . . . . .
O1 O 0.61711(16) 0.63639(15) 0.29806(14) 0.0358(4) Uani 1 1 d . . . . .
N1 N 0.51539(18) 0.49116(16) 0.28059(14) 0.0253(4) Uani 1 1 d . . . . .
N2 N 0.4160(3) 0.7024(2) 0.5083(2) 0.0574(8) Uani 1 1 d . . . . .
N3 N 0.2652(2) 0.44155(18) 0.46956(15) 0.0293(5) Uani 1 1 d . . . . .
N4 N 0.35246(18) 0.35916(17) 0.31358(14) 0.0271(4) Uani 1 1 d . . . . .
C1 C 0.5336(2) 0.5743(2) 0.32490(18) 0.0269(5) Uani 1 1 d . . . . .
C2 C 0.4355(2) 0.5669(2) 0.40472(17) 0.0276(5) Uani 1 1 d . . . . .
C3 C 0.3628(2) 0.4815(2) 0.41021(17) 0.0257(5) Uani 1 1 d . . . . .
C4 C 0.4107(2) 0.43232(19) 0.32890(16) 0.0240(5) Uani 1 1 d . . . . .
C5 C 0.4239(2) 0.6416(2) 0.4623(2) 0.0361(6) Uani 1 1 d . . . . .
C6 C 0.2122(2) 0.48425(19) 0.55117(17) 0.0243(5) Uani 1 1 d . . . . .
H6 H 0.2772 0.5053 0.5756 0.029 Uiso 1 1 calc R . . . .
C7 C 0.1393(2) 0.5826(2) 0.52890(18) 0.0298(5) Uani 1 1 d . . . . .
H7A H 0.0728 0.5642 0.5059 0.036 Uiso 1 1 calc R . . . .
H7B H 0.1879 0.6366 0.4821 0.036 Uiso 1 1 calc R . . . .
C8 C 0.0942(3) 0.6258(2) 0.6158(2) 0.0363(6) Uani 1 1 d . . . . .
H8A H 0.1613 0.6480 0.6362 0.044 Uiso 1 1 calc R . . . .
H8B H 0.0465 0.6878 0.6024 0.044 Uiso 1 1 calc R . . . .
C9 C 0.0206(3) 0.5427(2) 0.6915(2) 0.0389(7) Uani 1 1 d . . . . .
H9A H -0.0510 0.5262 0.6738 0.047 Uiso 1 1 calc R . . . .
H9B H -0.0027 0.5712 0.7466 0.047 Uiso 1 1 calc R . . . .
C10 C 0.0896(2) 0.4408(2) 0.71149(18) 0.0311(6) Uani 1 1 d . . . . .
H10A H 0.0379 0.3872 0.7563 0.037 Uiso 1 1 calc R . . . .
H10B H 0.1549 0.4553 0.7375 0.037 Uiso 1 1 calc R . . . .
C11 C 0.1382(2) 0.3977(2) 0.62467(17) 0.0278(5) Uani 1 1 d . . . . .
H11A H 0.1869 0.3364 0.6385 0.033 Uiso 1 1 calc R . . . .
H11B H 0.0730 0.3749 0.6025 0.033 Uiso 1 1 calc R . . . .
C12 C 0.3872(2) 0.31513(19) 0.23092(16) 0.0249(5) Uani 1 1 d . . . . .
H12 H 0.4543 0.3568 0.1884 0.030 Uiso 1 1 calc R . . . .
C13 C 0.4227(2) 0.1997(2) 0.25746(17) 0.0293(5) Uani 1 1 d . . . . .
H13A H 0.3573 0.1593 0.3015 0.035 Uiso 1 1 calc R . . . .
H13B H 0.4898 0.1968 0.2859 0.035 Uiso 1 1 calc R . . . .
C14 C 0.4557(2) 0.1501(2) 0.17299(18) 0.0307(6) Uani 1 1 d . . . . .
H14A H 0.5241 0.1880 0.1305 0.037 Uiso 1 1 calc R . . . .
H14B H 0.4768 0.0764 0.1909 0.037 Uiso 1 1 calc R . . . .
C15 C 0.3523(2) 0.1555(2) 0.12646(18) 0.0303(6) Uani 1 1 d . . . . .
H15A H 0.3761 0.1273 0.0713 0.036 Uiso 1 1 calc R . . . .
H15B H 0.2867 0.1117 0.1670 0.036 Uiso 1 1 calc R . . . .
C16 C 0.3121(3) 0.2695(2) 0.10201(19) 0.0338(6) Uani 1 1 d . . . . .
H16A H 0.2428 0.2699 0.0763 0.041 Uiso 1 1 calc R . . . .
H16B H 0.3745 0.3113 0.0559 0.041 Uiso 1 1 calc R . . . .
C17 C 0.2817(2) 0.3206(2) 0.18591(19) 0.0317(6) Uani 1 1 d . . . . .
H17A H 0.2612 0.3945 0.1675 0.038 Uiso 1 1 calc R . . . .
H17B H 0.2137 0.2836 0.2295 0.038 Uiso 1 1 calc R . . . .
C18 C 0.6145(2) 0.4557(2) 0.21896(17) 0.0249(5) Uani 1 1 d . . . . .
C19 C 0.6578(2) 0.5189(2) 0.13287(19) 0.0348(6) Uani 1 1 d . . . . .
H19 H 0.6208 0.5821 0.1139 0.042 Uiso 1 1 calc R . . . .
C20 C 0.7566(2) 0.4871(2) 0.07544(19) 0.0365(6) Uani 1 1 d . . . . .
H20 H 0.7864 0.5287 0.0175 0.044 Uiso 1 1 calc R . . . .
C21 C 0.8104(2) 0.3932(2) 0.10487(18) 0.0309(6) Uani 1 1 d . . . . .
C22 C 0.7696(2) 0.3307(2) 0.19070(18) 0.0300(5) Uani 1 1 d . . . . .
H22 H 0.8075 0.2681 0.2098 0.036 Uiso 1 1 calc R . . . .
C23 C 0.6707(2) 0.3632(2) 0.24825(17) 0.0273(5) Uani 1 1 d . . . . .
H23 H 0.6423 0.3225 0.3067 0.033 Uiso 1 1 calc R . . . .
Br1A Br 1.24044(3) 0.09721(3) 0.94220(2) 0.05541(12) Uani 1 1 d . . . . .
O1A O 1.01703(16) -0.14935(14) 0.69196(13) 0.0310(4) Uani 1 1 d . . . . .
N1A N 0.90802(17) 0.00175(16) 0.71363(13) 0.0224(4) Uani 1 1 d . . . . .
N2A N 0.9285(3) -0.2078(2) 0.48755(19) 0.0478(7) Uani 1 1 d . . . . .
N3A N 0.75369(19) 0.05919(18) 0.53301(14) 0.0261(4) Uani 1 1 d . . . . .
N4A N 0.76136(19) 0.14071(17) 0.68681(14) 0.0275(4) Uani 1 1 d . . . . .
C1A C 0.9480(2) -0.08314(19) 0.66838(17) 0.0235(5) Uani 1 1 d . . . . .
C2A C 0.8908(2) -0.07239(19) 0.59158(16) 0.0237(5) Uani 1 1 d . . . . .
C3A C 0.8215(2) 0.01683(19) 0.58889(16) 0.0222(5) Uani 1 1 d . . . . .
C4A C 0.8277(2) 0.06485(19) 0.66889(16) 0.0230(5) Uani 1 1 d . . . . .
C5A C 0.9109(2) -0.1467(2) 0.53355(18) 0.0299(5) Uani 1 1 d . . . . .
C6A C 0.7406(2) 0.01497(19) 0.45496(16) 0.0223(5) Uani 1 1 d . . . . .
H6A H 0.8191 -0.0074 0.4262 0.027 Uiso 1 1 calc R . . . .
C7A C 0.6579(2) -0.0834(2) 0.48471(17) 0.0261(5) Uani 1 1 d . . . . .
H7AA H 0.6859 -0.1362 0.5300 0.031 Uiso 1 1 calc R . . . .
H7AB H 0.5786 -0.0636 0.5122 0.031 Uiso 1 1 calc R . . . .
C8A C 0.6547(2) -0.1302(2) 0.40213(18) 0.0308(6) Uani 1 1 d . . . . .
H8AA H 0.6002 -0.1910 0.4209 0.037 Uiso 1 1 calc R . . . .
H8AB H 0.7330 -0.1549 0.3778 0.037 Uiso 1 1 calc R . . . .
C9A C 0.6157(2) -0.0478(2) 0.32741(18) 0.0312(6) Uani 1 1 d . . . . .
H9AA H 0.6204 -0.0781 0.2739 0.037 Uiso 1 1 calc R . . . .
H9AB H 0.5339 -0.0296 0.3491 0.037 Uiso 1 1 calc R . . . .
C10A C 0.6936(2) 0.0524(2) 0.30126(17) 0.0268(5) Uani 1 1 d . . . . .
H10C H 0.6630 0.1053 0.2576 0.032 Uiso 1 1 calc R . . . .
H10D H 0.7733 0.0357 0.2718 0.032 Uiso 1 1 calc R . . . .
C11A C 0.6988(2) 0.09899(19) 0.38399(16) 0.0245(5) Uani 1 1 d . . . . .
H11C H 0.7529 0.1602 0.3651 0.029 Uiso 1 1 calc R . . . .
H11D H 0.6208 0.1226 0.4102 0.029 Uiso 1 1 calc R . . . .
C12A C 0.7490(2) 0.1819(2) 0.77052(17) 0.0295(5) Uani 1 1 d . . . . .
H12A H 0.7968 0.1400 0.8099 0.035 Uiso 1 1 calc R . . . .
C13A C 0.7883(3) 0.2968(2) 0.7471(2) 0.0403(7) Uani 1 1 d . . . . .
H13C H 0.7422 0.3377 0.7070 0.048 Uiso 1 1 calc R . . . .
H13D H 0.8712 0.3033 0.7151 0.048 Uiso 1 1 calc R . . . .
C14A C 0.7722(3) 0.3412(3) 0.8341(2) 0.0485(8) Uani 1 1 d . . . . .
H14C H 0.8229 0.3035 0.8722 0.058 Uiso 1 1 calc R . . . .
H14D H 0.7961 0.4160 0.8178 0.058 Uiso 1 1 calc R . . . .
C15A C 0.6450(3) 0.3297(3) 0.8875(2) 0.0523(9) Uani 1 1 d . . . . .
H15C H 0.6393 0.3523 0.9448 0.063 Uiso 1 1 calc R . . . .
H15D H 0.5962 0.3761 0.8530 0.063 Uiso 1 1 calc R . . . .
C16A C 0.5987(3) 0.2181(3) 0.9071(2) 0.0555(9) Uani 1 1 d . . . . .
H16C H 0.5147 0.2162 0.9354 0.067 Uiso 1 1 calc R . . . .
H16D H 0.6385 0.1738 0.9503 0.067 Uiso 1 1 calc R . . . .
C17A C 0.6172(3) 0.1718(3) 0.8201(2) 0.0458(8) Uani 1 1 d . . . . .
H17C H 0.5920 0.0974 0.8365 0.055 Uiso 1 1 calc R . . . .
H17D H 0.5696 0.2100 0.7798 0.055 Uiso 1 1 calc R . . . .
C18A C 0.9766(2) 0.02990(19) 0.77248(16) 0.0230(5) Uani 1 1 d . . . . .
C19A C 0.9911(2) -0.0464(2) 0.84773(17) 0.0281(5) Uani 1 1 d . . . . .
H19A H 0.9491 -0.1109 0.8635 0.034 Uiso 1 1 calc R . . . .
C20A C 1.0687(2) -0.0258(2) 0.89944(17) 0.0322(6) Uani 1 1 d . . . . .
H20A H 1.0800 -0.0766 0.9496 0.039 Uiso 1 1 calc R . . . .
C21A C 1.1289(2) 0.0713(2) 0.87520(18) 0.0324(6) Uani 1 1 d . . . . .
C22A C 1.1133(2) 0.1483(2) 0.80191(18) 0.0311(6) Uani 1 1 d . . . . .
H22A H 1.1531 0.2138 0.7877 0.037 Uiso 1 1 calc R . . . .
C23A C 1.0373(2) 0.1270(2) 0.74937(17) 0.0265(5) Uani 1 1 d . . . . .
H23A H 1.0273 0.1776 0.6988 0.032 Uiso 1 1 calc R . . . .
H3 H 0.228(3) 0.387(3) 0.459(2) 0.040(9) Uiso 1 1 d . . . . .
H3A H 0.718(3) 0.112(3) 0.544(2) 0.039(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C21 1.906(3) . ?
O1 C1 1.209(3) . ?
N1 C1 1.423(3) . ?
N1 C4 1.412(3) . ?
N1 C18 1.442(3) . ?
N2 C5 1.145(4) . ?
N3 C3 1.318(3) . ?
N3 C6 1.471(3) . ?
N3 H3 0.89(3) . ?
N4 C4 1.260(3) . ?
N4 C12 1.465(3) . ?
C1 C2 1.458(4) . ?
C2 C3 1.376(3) . ?
C2 C5 1.418(4) . ?
C3 C4 1.503(3) . ?
C6 H6 0.9800 . ?
C6 C7 1.522(3) . ?
C6 C11 1.525(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.528(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.514(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.526(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.533(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9800 . ?
C12 C13 1.523(4) . ?
C12 C17 1.527(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.529(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.520(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.520(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.532(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.388(4) . ?
C18 C23 1.378(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.379(4) . ?
C21 C22 1.377(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.391(3) . ?
C23 H23 0.9300 . ?
Br1A C21A 1.898(3) . ?
O1A C1A 1.207(3) . ?
N1A C1A 1.423(3) . ?
N1A C4A 1.418(3) . ?
N1A C18A 1.433(3) . ?
N2A C5A 1.146(3) . ?
N3A C3A 1.318(3) . ?
N3A C6A 1.466(3) . ?
N3A H3A 0.81(3) . ?
N4A C4A 1.261(3) . ?
N4A C12A 1.465(3) . ?
C1A C2A 1.459(3) . ?
C2A C3A 1.379(3) . ?
C2A C5A 1.415(3) . ?
C3A C4A 1.500(3) . ?
C6A H6A 0.9800 . ?
C6A C7A 1.530(3) . ?
C6A C11A 1.518(3) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C7A C8A 1.519(4) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C8A C9A 1.529(4) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C9A C10A 1.519(4) . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
C10A C11A 1.525(3) . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C12A H12A 0.9800 . ?
C12A C13A 1.499(4) . ?
C12A C17A 1.538(4) . ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?
C13A C14A 1.530(4) . ?
C14A H14C 0.9700 . ?
C14A H14D 0.9700 . ?
C14A C15A 1.508(5) . ?
C15A H15C 0.9700 . ?
C15A H15D 0.9700 . ?
C15A C16A 1.488(5) . ?
C16A H16C 0.9700 . ?
C16A H16D 0.9700 . ?
C16A C17A 1.541(4) . ?
C17A H17C 0.9700 . ?
C17A H17D 0.9700 . ?
C18A C19A 1.388(3) . ?
C18A C23A 1.385(3) . ?
C19A H19A 0.9300 . ?
C19A C20A 1.390(4) . ?
C20A H20A 0.9300 . ?
C20A C21A 1.382(4) . ?
C21A C22A 1.375(4) . ?
C22A H22A 0.9300 . ?
C22A C23A 1.388(3) . ?
C23A H23A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C18 119.2(2) . . ?
C4 N1 C1 110.03(19) . . ?
C4 N1 C18 127.0(2) . . ?
C3 N3 C6 123.4(2) . . ?
C3 N3 H3 118(2) . . ?
C6 N3 H3 118(2) . . ?
C4 N4 C12 123.0(2) . . ?
O1 C1 N1 123.7(2) . . ?
O1 C1 C2 129.4(2) . . ?
N1 C1 C2 106.9(2) . . ?
C3 C2 C1 109.2(2) . . ?
C3 C2 C5 129.3(2) . . ?
C5 C2 C1 121.4(2) . . ?
N3 C3 C2 132.3(2) . . ?
N3 C3 C4 119.6(2) . . ?
C2 C3 C4 108.1(2) . . ?
N1 C4 C3 105.7(2) . . ?
N4 C4 N1 134.1(2) . . ?
N4 C4 C3 120.0(2) . . ?
N2 C5 C2 179.1(3) . . ?
N3 C6 H6 107.7 . . ?
N3 C6 C7 112.2(2) . . ?
N3 C6 C11 110.12(19) . . ?
C7 C6 H6 107.7 . . ?
C7 C6 C11 111.2(2) . . ?
C11 C6 H6 107.7 . . ?
C6 C7 H7A 109.9 . . ?
C6 C7 H7B 109.9 . . ?
C6 C7 C8 108.8(2) . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 C7 111.5(2) . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C8 C9 C10 111.3(2) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C9 C10 C11 111.6(2) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C6 C11 C10 109.8(2) . . ?
C6 C11 H11A 109.7 . . ?
C6 C11 H11B 109.7 . . ?
C10 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
N4 C12 H12 109.7 . . ?
N4 C12 C13 109.0(2) . . ?
N4 C12 C17 108.7(2) . . ?
C13 C12 H12 109.7 . . ?
C13 C12 C17 110.0(2) . . ?
C17 C12 H12 109.7 . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C12 C13 C14 110.4(2) . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 C13 110.4(2) . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 C14 111.2(2) . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C15 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C15 C16 C17 111.5(2) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C12 C17 C16 110.4(2) . . ?
C12 C17 H17A 109.6 . . ?
C12 C17 H17B 109.6 . . ?
C16 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C19 C18 N1 119.5(2) . . ?
C23 C18 N1 119.8(2) . . ?
C23 C18 C19 120.5(2) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.4(2) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.4(2) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 Br1 119.6(2) . . ?
C22 C21 Br1 118.7(2) . . ?
C22 C21 C20 121.7(2) . . ?
C21 C22 H22 120.7 . . ?
C21 C22 C23 118.6(2) . . ?
C23 C22 H22 120.7 . . ?
C18 C23 C22 120.3(2) . . ?
C18 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C1A N1A C18A 118.04(19) . . ?
C4A N1A C1A 109.88(19) . . ?
C4A N1A C18A 128.75(19) . . ?
C3A N3A C6A 123.1(2) . . ?
C3A N3A H3A 116(2) . . ?
C6A N3A H3A 120(2) . . ?
C4A N4A C12A 123.6(2) . . ?
O1A C1A N1A 124.1(2) . . ?
O1A C1A C2A 128.8(2) . . ?
N1A C1A C2A 107.1(2) . . ?
C3A C2A C1A 108.9(2) . . ?
C3A C2A C5A 130.1(2) . . ?
C5A C2A C1A 121.0(2) . . ?
N3A C3A C2A 131.6(2) . . ?
N3A C3A C4A 120.0(2) . . ?
C2A C3A C4A 108.3(2) . . ?
N1A C4A C3A 105.68(19) . . ?
N4A C4A N1A 134.0(2) . . ?
N4A C4A C3A 120.1(2) . . ?
N2A C5A C2A 178.7(3) . . ?
N3A C6A H6A 107.6 . . ?
N3A C6A C7A 112.0(2) . . ?
N3A C6A C11A 111.00(19) . . ?
C7A C6A H6A 107.6 . . ?
C11A C6A H6A 107.6 . . ?
C11A C6A C7A 110.85(19) . . ?
C6A C7A H7AA 109.8 . . ?
C6A C7A H7AB 109.8 . . ?
H7AA C7A H7AB 108.2 . . ?
C8A C7A C6A 109.6(2) . . ?
C8A C7A H7AA 109.8 . . ?
C8A C7A H7AB 109.8 . . ?
C7A C8A H8AA 109.4 . . ?
C7A C8A H8AB 109.4 . . ?
C7A C8A C9A 111.3(2) . . ?
H8AA C8A H8AB 108.0 . . ?
C9A C8A H8AA 109.4 . . ?
C9A C8A H8AB 109.4 . . ?
C8A C9A H9AA 109.5 . . ?
C8A C9A H9AB 109.5 . . ?
H9AA C9A H9AB 108.0 . . ?
C10A C9A C8A 110.9(2) . . ?
C10A C9A H9AA 109.5 . . ?
C10A C9A H9AB 109.5 . . ?
C9A C10A H10C 109.2 . . ?
C9A C10A H10D 109.2 . . ?
C9A C10A C11A 112.2(2) . . ?
H10C C10A H10D 107.9 . . ?
C11A C10A H10C 109.2 . . ?
C11A C10A H10D 109.2 . . ?
C6A C11A C10A 109.62(19) . . ?
C6A C11A H11C 109.7 . . ?
C6A C11A H11D 109.7 . . ?
C10A C11A H11C 109.7 . . ?
C10A C11A H11D 109.7 . . ?
H11C C11A H11D 108.2 . . ?
N4A C12A H12A 109.8 . . ?
N4A C12A C13A 110.1(2) . . ?
N4A C12A C17A 107.7(2) . . ?
C13A C12A H12A 109.8 . . ?
C13A C12A C17A 109.6(2) . . ?
C17A C12A H12A 109.8 . . ?
C12A C13A H13C 109.6 . . ?
C12A C13A H13D 109.6 . . ?
C12A C13A C14A 110.3(3) . . ?
H13C C13A H13D 108.1 . . ?
C14A C13A H13C 109.6 . . ?
C14A C13A H13D 109.6 . . ?
C13A C14A H14C 109.4 . . ?
C13A C14A H14D 109.4 . . ?
H14C C14A H14D 108.0 . . ?
C15A C14A C13A 111.3(3) . . ?
C15A C14A H14C 109.4 . . ?
C15A C14A H14D 109.4 . . ?
C14A C15A H15C 109.2 . . ?
C14A C15A H15D 109.2 . . ?
H15C C15A H15D 107.9 . . ?
C16A C15A C14A 112.3(3) . . ?
C16A C15A H15C 109.2 . . ?
C16A C15A H15D 109.2 . . ?
C15A C16A H16C 109.1 . . ?
C15A C16A H16D 109.1 . . ?
C15A C16A C17A 112.4(3) . . ?
H16C C16A H16D 107.9 . . ?
C17A C16A H16C 109.1 . . ?
C17A C16A H16D 109.1 . . ?
C12A C17A C16A 109.7(3) . . ?
C12A C17A H17C 109.7 . . ?
C12A C17A H17D 109.7 . . ?
C16A C17A H17C 109.7 . . ?
C16A C17A H17D 109.7 . . ?
H17C C17A H17D 108.2 . . ?
C19A C18A N1A 118.5(2) . . ?
C23A C18A N1A 120.6(2) . . ?
C23A C18A C19A 120.6(2) . . ?
C18A C19A H19A 120.2 . . ?
C18A C19A C20A 119.6(2) . . ?
C20A C19A H19A 120.2 . . ?
C19A C20A H20A 120.5 . . ?
C21A C20A C19A 119.0(2) . . ?
C21A C20A H20A 120.5 . . ?
C20A C21A Br1A 119.1(2) . . ?
C22A C21A Br1A 119.1(2) . . ?
C22A C21A C20A 121.8(2) . . ?
C21A C22A H22A 120.4 . . ?
C21A C22A C23A 119.1(2) . . ?
C23A C22A H22A 120.4 . . ?
C18A C23A C22A 119.8(2) . . ?
C18A C23A H23A 120.1 . . ?
C22A C23A H23A 120.1 . . ?

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 C21 C22 C23 179.59(19) . . . . ?
O1 C1 C2 C3 -178.0(3) . . . . ?
O1 C1 C2 C5 3.1(4) . . . . ?
N1 C1 C2 C3 1.6(3) . . . . ?
N1 C1 C2 C5 -177.3(2) . . . . ?
N1 C18 C19 C20 176.9(2) . . . . ?
N1 C18 C23 C22 -177.1(2) . . . . ?
N3 C3 C4 N1 -178.9(2) . . . . ?
N3 C3 C4 N4 5.9(4) . . . . ?
N3 C6 C7 C8 -176.5(2) . . . . ?
N3 C6 C11 C10 176.6(2) . . . . ?
N4 C12 C13 C14 178.2(2) . . . . ?
N4 C12 C17 C16 -176.8(2) . . . . ?
C1 N1 C4 N4 172.8(3) . . . . ?
C1 N1 C4 C3 -1.5(3) . . . . ?
C1 N1 C18 C19 -74.5(3) . . . . ?
C1 N1 C18 C23 100.9(3) . . . . ?
C1 C2 C3 N3 179.1(3) . . . . ?
C1 C2 C3 C4 -2.5(3) . . . . ?
C2 C3 C4 N1 2.5(3) . . . . ?
C2 C3 C4 N4 -172.8(2) . . . . ?
C3 N3 C6 C7 80.5(3) . . . . ?
C3 N3 C6 C11 -155.0(2) . . . . ?
C4 N1 C1 O1 179.6(2) . . . . ?
C4 N1 C1 C2 0.0(3) . . . . ?
C4 N1 C18 C19 129.8(3) . . . . ?
C4 N1 C18 C23 -54.9(3) . . . . ?
C4 N4 C12 C13 113.3(3) . . . . ?
C4 N4 C12 C17 -126.8(3) . . . . ?
C5 C2 C3 N3 -2.1(5) . . . . ?
C5 C2 C3 C4 176.3(3) . . . . ?
C6 N3 C3 C2 -2.0(4) . . . . ?
C6 N3 C3 C4 179.8(2) . . . . ?
C6 C7 C8 C9 -58.0(3) . . . . ?
C7 C6 C11 C10 -58.3(3) . . . . ?
C7 C8 C9 C10 55.7(3) . . . . ?
C8 C9 C10 C11 -53.9(3) . . . . ?
C9 C10 C11 C6 54.8(3) . . . . ?
C11 C6 C7 C8 59.6(3) . . . . ?
C12 N4 C4 N1 -0.1(4) . . . . ?
C12 N4 C4 C3 173.5(2) . . . . ?
C12 C13 C14 C15 -58.3(3) . . . . ?
C13 C12 C17 C16 -57.5(3) . . . . ?
C13 C14 C15 C16 56.1(3) . . . . ?
C14 C15 C16 C17 -55.1(3) . . . . ?
C15 C16 C17 C12 55.7(3) . . . . ?
C17 C12 C13 C14 59.1(3) . . . . ?
C18 N1 C1 O1 20.0(4) . . . . ?
C18 N1 C1 C2 -159.6(2) . . . . ?
C18 N1 C4 N4 -29.6(4) . . . . ?
C18 N1 C4 C3 156.1(2) . . . . ?
C18 C19 C20 C21 -0.1(4) . . . . ?
C19 C18 C23 C22 -1.8(4) . . . . ?
C19 C20 C21 Br1 -179.8(2) . . . . ?
C19 C20 C21 C22 -1.1(4) . . . . ?
C20 C21 C22 C23 0.8(4) . . . . ?
C21 C22 C23 C18 0.6(4) . . . . ?
C23 C18 C19 C20 1.6(4) . . . . ?
Br1A C21A C22A C23A 175.99(19) . . . . ?
O1A C1A C2A C3A -178.2(2) . . . . ?
O1A C1A C2A C5A 1.5(4) . . . . ?
N1A C1A C2A C3A 1.5(3) . . . . ?
N1A C1A C2A C5A -178.8(2) . . . . ?
N1A C18A C19A C20A 172.2(2) . . . . ?
N1A C18A C23A C22A -173.2(2) . . . . ?
N3A C3A C4A N1A -179.5(2) . . . . ?
N3A C3A C4A N4A 5.3(4) . . . . ?
N3A C6A C7A C8A -176.0(2) . . . . ?
N3A C6A C11A C10A 176.46(19) . . . . ?
N4A C12A C13A C14A 178.3(2) . . . . ?
N4A C12A C17A C16A -177.9(3) . . . . ?
C1A N1A C4A N4A 172.3(3) . . . . ?
C1A N1A C4A C3A -1.9(2) . . . . ?
C1A N1A C18A C19A -61.0(3) . . . . ?
C1A N1A C18A C23A 112.2(3) . . . . ?
C1A C2A C3A N3A -180.0(2) . . . . ?
C1A C2A C3A C4A -2.7(3) . . . . ?
C2A C3A C4A N1A 2.9(3) . . . . ?
C2A C3A C4A N4A -172.3(2) . . . . ?
C3A N3A C6A C7A 77.4(3) . . . . ?
C3A N3A C6A C11A -158.1(2) . . . . ?
C4A N1A C1A O1A -179.9(2) . . . . ?
C4A N1A C1A C2A 0.3(3) . . . . ?
C4A N1A C18A C19A 141.8(2) . . . . ?
C4A N1A C18A C23A -45.0(3) . . . . ?
C4A N4A C12A C13A 118.8(3) . . . . ?
C4A N4A C12A C17A -121.8(3) . . . . ?
C5A C2A C3A N3A 0.4(5) . . . . ?
C5A C2A C3A C4A 177.7(3) . . . . ?
C6A N3A C3A C2A -1.3(4) . . . . ?
C6A N3A C3A C4A -178.3(2) . . . . ?
C6A C7A C8A C9A -57.1(3) . . . . ?
C7A C6A C11A C10A -58.4(3) . . . . ?
C7A C8A C9A C10A 54.8(3) . . . . ?
C8A C9A C10A C11A -54.2(3) . . . . ?
C9A C10A C11A C6A 56.0(3) . . . . ?
C11A C6A C7A C8A 59.4(3) . . . . ?
C12A N4A C4A N1A -2.7(4) . . . . ?
C12A N4A C4A C3A 170.8(2) . . . . ?
C12A C13A C14A C15A -57.6(4) . . . . ?
C13A C12A C17A C16A -58.1(3) . . . . ?
C13A C14A C15A C16A 53.5(4) . . . . ?
C14A C15A C16A C17A -52.6(4) . . . . ?
C15A C16A C17A C12A 54.6(4) . . . . ?
C17A C12A C13A C14A 60.0(3) . . . . ?
C18A N1A C1A O1A 18.9(3) . . . . ?
C18A N1A C1A C2A -160.9(2) . . . . ?
C18A N1A C4A N4A -29.1(4) . . . . ?
C18A N1A C4A C3A 156.7(2) . . . . ?
C18A C19A C20A C21A 0.8(4) . . . . ?
C19A C18A C23A C22A -0.1(4) . . . . ?
C19A C20A C21A Br1A -177.11(19) . . . . ?
C19A C20A C21A C22A 0.5(4) . . . . ?
C20A C21A C22A C23A -1.7(4) . . . . ?
C21A C22A C23A C18A 1.4(4) . . . . ?
C23A C18A C19A C20A -1.0(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
