# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_mo_cxy0344_0m
_database_code_depnum_ccdc_archive 'CCDC 1903686'
loop_
_audit_author_name
_audit_author_address
'Pengfei Li' 'Southern University of Science and Technology'
_audit_update_record             
;
2019-03-18 deposited with the CCDC.	2019-08-28 downloaded from the CCDC.
;
_audit_creation_date             2018-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 Br N5 O3'
_chemical_formula_sum            'C22 H22 Br N5 O3'
_chemical_formula_weight         484.35
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   10.2380(4)
_cell_length_b                   10.6914(5)
_cell_length_c                   19.2761(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2109.93(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9752
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   0.544
_shelx_estimated_absorpt_T_min   0.512
_exptl_absorpt_coefficient_mu    1.983
_exptl_absorpt_correction_T_max  0.2616
_exptl_absorpt_correction_T_min  0.1961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0746 before and 0.0532 after correction. The Ratio of minimum to maximum transmission is 0.7496. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            45681
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         2.252
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD 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 PHOTO 100 area detector'
_diffrn_measurement_method       'φ and ω 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         0.763
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4723
_reflns_number_total             4871
_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       ?
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1974 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(2)
_refine_ls_extinction_coef       0.0061(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4871
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0196
_refine_ls_restrained_S_all      1.044
_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)+(0.0155P)²+0.8990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0435
_refine_ls_wR_factor_ref         0.0441
_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.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C14(H14), C15(H15), C16(H16), C17(H17),
 C19(H19), C20(H20), C22(H22)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C23(H23A,H23B,H23C)
;
_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 0.64178(2) -0.05177(2) 0.36488(2) 0.01800(7) Uani 1 1 d . . . . .
O1 O 0.24459(14) 0.09495(14) 0.65640(7) 0.0132(3) Uani 1 1 d . . . . .
O2 O 0.66953(14) 0.22405(14) 0.73335(7) 0.0148(3) Uani 1 1 d . . . . .
O3 O 0.36383(16) -0.02742(13) 0.58284(7) 0.0144(3) Uani 1 1 d . . . . .
N1 N 0.74138(17) 0.25500(16) 0.62124(8) 0.0120(4) Uani 1 1 d . . . . .
N2 N 0.45670(16) 0.12368(16) 0.65101(9) 0.0108(4) Uani 1 1 d . . . . .
H2 H 0.4400 0.1908 0.6758 0.013 Uiso 1 1 calc R . . . .
N3 N 0.62251(16) -0.02871(15) 0.67280(9) 0.0103(3) Uani 1 1 d . . . . .
N4 N 0.74787(17) -0.07117(17) 0.67200(9) 0.0148(4) Uani 1 1 d . . . . .
C1 C 0.5683(3) 0.6900(2) 0.57517(13) 0.0226(5) Uani 1 1 d . . . . .
H1 H 0.5156 0.7600 0.5634 0.027 Uiso 1 1 calc R . . . .
C2 C 0.5139(2) 0.5886(2) 0.60858(14) 0.0231(5) Uani 1 1 d . . . . .
H2A H 0.4238 0.5892 0.6203 0.028 Uiso 1 1 calc R . . . .
C3 C 0.5903(2) 0.4857(2) 0.62523(12) 0.0187(5) Uani 1 1 d . . . . .
H3 H 0.5516 0.4154 0.6473 0.022 Uiso 1 1 calc R . . . .
C4 C 0.7236(2) 0.4846(2) 0.60978(11) 0.0138(4) Uani 1 1 d . . . . .
C5 C 0.8083(2) 0.37428(18) 0.63072(12) 0.0140(4) Uani 1 1 d . . . . .
H5A H 0.8892 0.3747 0.6026 0.017 Uiso 1 1 calc R . . . .
H5B H 0.8335 0.3833 0.6800 0.017 Uiso 1 1 calc R . . . .
C6 C 0.67278(19) 0.19677(19) 0.67231(11) 0.0114(4) Uani 1 1 d . . . . .
C7 C 0.59076(19) 0.08962(17) 0.63824(11) 0.0104(4) Uani 1 1 d . . . . .
C8 C 0.35409(19) 0.05440(18) 0.62556(9) 0.0110(3) Uani 1 1 d . . . . .
C9 C 0.11568(18) 0.0350(2) 0.64371(11) 0.0135(4) Uani 1 1 d . . . . .
C10 C 0.1232(2) -0.1053(2) 0.65523(12) 0.0197(5) Uani 1 1 d . . . . .
H10A H 0.1699 -0.1443 0.6165 0.030 Uiso 1 1 calc GR . . . .
H10B H 0.0347 -0.1399 0.6581 0.030 Uiso 1 1 calc GR . . . .
H10C H 0.1699 -0.1224 0.6986 0.030 Uiso 1 1 calc GR . . . .
C11 C 0.0680(2) 0.0652(2) 0.57101(11) 0.0184(5) Uani 1 1 d . . . . .
H11A H 0.0617 0.1562 0.5655 0.028 Uiso 1 1 calc GR . . . .
H11B H -0.0182 0.0275 0.5638 0.028 Uiso 1 1 calc GR . . . .
H11C H 0.1297 0.0316 0.5369 0.028 Uiso 1 1 calc GR . . . .
C12 C 0.6376(2) 0.09510(18) 0.56325(10) 0.0101(4) Uani 1 1 d . . . . .
C13 C 0.7245(2) 0.19472(19) 0.55685(11) 0.0112(4) Uani 1 1 d . . . . .
C14 C 0.7000(2) 0.6895(2) 0.55879(13) 0.0219(5) Uani 1 1 d . . . . .
H14 H 0.7376 0.7590 0.5355 0.026 Uiso 1 1 calc R . . . .
C15 C 0.7772(2) 0.5873(2) 0.57629(12) 0.0182(5) Uani 1 1 d . . . . .
H15 H 0.8676 0.5878 0.5652 0.022 Uiso 1 1 calc R . . . .
C16 C 0.7872(2) 0.2227(2) 0.49552(11) 0.0141(4) Uani 1 1 d . . . . .
H16 H 0.8461 0.2911 0.4924 0.017 Uiso 1 1 calc R . . . .
C17 C 0.7613(2) 0.1473(2) 0.43813(11) 0.0147(4) Uani 1 1 d . . . . .
H17 H 0.8025 0.1638 0.3949 0.018 Uiso 1 1 calc R . . . .
C18 C 0.67515(18) 0.0480(2) 0.44447(10) 0.0124(4) Uani 1 1 d . . . . .
C19 C 0.61233(19) 0.01921(18) 0.50663(11) 0.0120(4) Uani 1 1 d . . . . .
H19 H 0.5544 -0.0499 0.5100 0.014 Uiso 1 1 calc R . . . .
C20 C 0.7417(2) -0.1675(2) 0.71469(12) 0.0166(4) Uani 1 1 d . . . . .
H20 H 0.8156 -0.2180 0.7249 0.020 Uiso 1 1 calc R . . . .
N5 N 0.62279(18) -0.18943(17) 0.74285(10) 0.0176(4) Uani 1 1 d . . . . .
C22 C 0.5505(2) -0.0998(2) 0.71547(11) 0.0165(4) Uani 1 1 d . . . . .
H22 H 0.4603 -0.0875 0.7247 0.020 Uiso 1 1 calc R . . . .
C23 C 0.0320(2) 0.0982(2) 0.69811(13) 0.0208(5) Uani 1 1 d . . . . .
H23A H 0.0660 0.0785 0.7444 0.031 Uiso 1 1 calc GR . . . .
H23B H -0.0581 0.0680 0.6942 0.031 Uiso 1 1 calc GR . . . .
H23C H 0.0338 0.1889 0.6910 0.031 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C18 1.900(2) . ?
O1 C8 1.341(2) . ?
O1 C9 1.487(2) . ?
O2 C6 1.213(3) . ?
O3 C8 1.206(2) . ?
N1 C5 1.459(2) . ?
N1 C6 1.360(3) . ?
N1 C13 1.409(3) . ?
N2 H2 0.8800 . ?
N2 C7 1.441(2) . ?
N2 C8 1.376(3) . ?
N3 N4 1.361(2) . ?
N3 C7 1.466(2) . ?
N3 C22 1.341(3) . ?
N4 C20 1.320(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.378(3) . ?
C1 C14 1.385(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(3) . ?
C4 C5 1.519(3) . ?
C4 C15 1.387(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.565(3) . ?
C7 C12 1.524(3) . ?
C9 C10 1.518(3) . ?
C9 C11 1.519(3) . ?
C9 C23 1.513(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.393(3) . ?
C12 C19 1.384(3) . ?
C13 C16 1.378(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.394(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(3) . ?
C18 C19 1.394(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C20 N5 1.354(3) . ?
N5 C22 1.321(3) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C9 121.97(15) . . ?
C6 N1 C5 123.49(18) . . ?
C6 N1 C13 111.39(17) . . ?
C13 N1 C5 124.59(17) . . ?
C7 N2 H2 119.0 . . ?
C8 N2 H2 119.0 . . ?
C8 N2 C7 122.02(17) . . ?
N4 N3 C7 119.44(16) . . ?
C22 N3 N4 109.65(17) . . ?
C22 N3 C7 130.23(18) . . ?
C20 N4 N3 102.03(17) . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C14 119.8(2) . . ?
C14 C1 H1 120.1 . . ?
C1 C2 H2A 119.9 . . ?
C1 C2 C3 120.3(2) . . ?
C3 C2 H2A 119.9 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 120.5(2) . . ?
C15 C4 C3 118.6(2) . . ?
C15 C4 C5 120.8(2) . . ?
N1 C5 C4 112.18(16) . . ?
N1 C5 H5A 109.2 . . ?
N1 C5 H5B 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
O2 C6 N1 127.32(19) . . ?
O2 C6 C7 124.65(19) . . ?
N1 C6 C7 107.97(17) . . ?
N2 C7 N3 110.58(16) . . ?
N2 C7 C6 104.74(15) . . ?
N2 C7 C12 116.87(17) . . ?
N3 C7 C6 108.79(16) . . ?
N3 C7 C12 113.22(16) . . ?
C12 C7 C6 101.59(15) . . ?
O1 C8 N2 107.83(16) . . ?
O3 C8 O1 127.34(18) . . ?
O3 C8 N2 124.82(18) . . ?
O1 C9 C10 110.89(17) . . ?
O1 C9 C11 110.18(17) . . ?
O1 C9 C23 101.32(16) . . ?
C10 C9 C11 111.21(19) . . ?
C23 C9 C10 111.62(19) . . ?
C23 C9 C11 111.23(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C7 108.32(17) . . ?
C19 C12 C7 131.78(18) . . ?
C19 C12 C13 119.85(18) . . ?
C12 C13 N1 110.49(17) . . ?
C16 C13 N1 126.82(19) . . ?
C16 C13 C12 122.62(19) . . ?
C1 C14 H14 119.9 . . ?
C1 C14 C15 120.1(2) . . ?
C15 C14 H14 119.9 . . ?
C4 C15 C14 120.7(2) . . ?
C4 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C13 C16 H16 121.1 . . ?
C13 C16 C17 117.8(2) . . ?
C17 C16 H16 121.1 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.59(19) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 Br1 118.26(15) . . ?
C17 C18 C19 122.60(19) . . ?
C19 C18 Br1 119.15(16) . . ?
C12 C19 C18 117.50(18) . . ?
C12 C19 H19 121.2 . . ?
C18 C19 H19 121.2 . . ?
N4 C20 H20 122.3 . . ?
N4 C20 N5 115.3(2) . . ?
N5 C20 H20 122.3 . . ?
C22 N5 C20 102.61(18) . . ?
N3 C22 H22 124.8 . . ?
N5 C22 N3 110.37(19) . . ?
N5 C22 H22 124.8 . . ?
C9 C23 H23A 109.5 . . ?
C9 C23 H23B 109.5 . . ?
C9 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C18 C19 C12 -179.09(15) . . . . ?
O2 C6 C7 N2 60.0(2) . . . . ?
O2 C6 C7 N3 -58.2(2) . . . . ?
O2 C6 C7 C12 -177.88(19) . . . . ?
N1 C6 C7 N2 -117.25(18) . . . . ?
N1 C6 C7 N3 124.49(17) . . . . ?
N1 C6 C7 C12 4.8(2) . . . . ?
N1 C13 C16 C17 176.80(19) . . . . ?
N2 C7 C12 C13 109.9(2) . . . . ?
N2 C7 C12 C19 -72.8(3) . . . . ?
N3 N4 C20 N5 -0.3(2) . . . . ?
N3 C7 C12 C13 -119.87(18) . . . . ?
N3 C7 C12 C19 57.4(3) . . . . ?
N4 N3 C7 N2 -174.25(16) . . . . ?
N4 N3 C7 C6 -59.8(2) . . . . ?
N4 N3 C7 C12 52.4(2) . . . . ?
N4 N3 C22 N5 -0.7(2) . . . . ?
N4 C20 N5 C22 -0.1(3) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C1 C14 C15 C4 0.5(4) . . . . ?
C2 C1 C14 C15 -0.3(4) . . . . ?
C2 C3 C4 C5 177.4(2) . . . . ?
C2 C3 C4 C15 -1.3(3) . . . . ?
C3 C4 C5 N1 39.4(3) . . . . ?
C3 C4 C15 C14 0.3(3) . . . . ?
C5 N1 C6 O2 -9.8(3) . . . . ?
C5 N1 C6 C7 167.38(17) . . . . ?
C5 N1 C13 C12 -169.46(18) . . . . ?
C5 N1 C13 C16 13.5(3) . . . . ?
C5 C4 C15 C14 -178.3(2) . . . . ?
C6 N1 C5 C4 -93.3(2) . . . . ?
C6 N1 C13 C12 2.4(2) . . . . ?
C6 N1 C13 C16 -174.6(2) . . . . ?
C6 C7 C12 C13 -3.4(2) . . . . ?
C6 C7 C12 C19 173.9(2) . . . . ?
C7 N2 C8 O1 168.61(17) . . . . ?
C7 N2 C8 O3 -11.7(3) . . . . ?
C7 N3 N4 C20 172.10(17) . . . . ?
C7 N3 C22 N5 -170.98(19) . . . . ?
C7 C12 C13 N1 1.0(2) . . . . ?
C7 C12 C13 C16 178.16(19) . . . . ?
C7 C12 C19 C18 -177.9(2) . . . . ?
C8 O1 C9 C10 52.2(2) . . . . ?
C8 O1 C9 C11 -71.4(2) . . . . ?
C8 O1 C9 C23 170.77(18) . . . . ?
C8 N2 C7 N3 -66.3(2) . . . . ?
C8 N2 C7 C6 176.72(17) . . . . ?
C8 N2 C7 C12 65.2(2) . . . . ?
C9 O1 C8 O3 3.9(3) . . . . ?
C9 O1 C8 N2 -176.43(16) . . . . ?
C12 C13 C16 C17 0.1(3) . . . . ?
C13 N1 C5 C4 77.6(2) . . . . ?
C13 N1 C6 O2 178.2(2) . . . . ?
C13 N1 C6 C7 -4.6(2) . . . . ?
C13 C12 C19 C18 -0.9(3) . . . . ?
C13 C16 C17 C18 -0.2(3) . . . . ?
C14 C1 C2 C3 -0.6(4) . . . . ?
C15 C4 C5 N1 -141.9(2) . . . . ?
C16 C17 C18 Br1 179.61(16) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C12 0.8(3) . . . . ?
C19 C12 C13 N1 -176.73(18) . . . . ?
C19 C12 C13 C16 0.5(3) . . . . ?
C20 N5 C22 N3 0.4(2) . . . . ?
C22 N3 N4 C20 0.6(2) . . . . ?
C22 N3 C7 N2 -4.7(3) . . . . ?
C22 N3 C7 C6 109.8(2) . . . . ?
C22 N3 C7 C12 -138.1(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_cxy0376
_database_code_depnum_ccdc_archive 'CCDC 1903690'
loop_
_audit_author_name
_audit_author_address
'Pengfei Li' 'Southern University of Science and Technology'
_audit_update_record             
;
2019-03-18 deposited with the CCDC.	2019-08-28 downloaded from the CCDC.
;
_audit_creation_date             2018-05-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H24 Br N5 O3'
_chemical_formula_sum            'C26 H24 Br N5 O3'
_chemical_formula_weight         534.41
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   17.594(2)
_cell_length_b                   10.7941(13)
_cell_length_c                   25.355(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4815.1(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9073
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   0.572
_shelx_estimated_absorpt_T_min   0.542
_exptl_absorpt_coefficient_mu    1.746
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0829 before and 0.0531 after correction. The Ratio of minimum to maximum transmission is 0.7910. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            41959
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_min         2.315
_diffrn_ambient_temperature      150
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_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                4330
_reflns_number_total             5532
_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       ?
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.00126(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5532
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.018
_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)+(0.0263P)²+5.4892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0821
_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.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C16(H16), C18(H18),
 C19(H19), C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C26(H26A,H26B,H26C)
;
_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 0.64613(2) 0.78776(2) 0.75817(2) 0.02805(9) Uani 1 1 d . . . . .
O1 O 0.48417(8) 0.70889(12) 0.59487(5) 0.0186(3) Uani 1 1 d . . . . .
O2 O 0.44794(8) 0.26237(14) 0.60674(6) 0.0220(3) Uani 1 1 d . . . . .
O3 O 0.52101(9) 0.64315(14) 0.51365(6) 0.0252(4) Uani 1 1 d . . . . .
N1 N 0.50401(9) 0.50709(16) 0.58074(6) 0.0156(4) Uani 1 1 d . . . . .
H1 H 0.520083 0.446066 0.560605 0.019 Uiso 1 1 calc R . . . .
N2 N 0.53720(10) 0.29912(15) 0.67179(7) 0.0172(4) Uani 1 1 d . . . . .
N3 N 0.40208(9) 0.52069(16) 0.64411(6) 0.0151(4) Uani 1 1 d . . . . .
N4 N 0.38718(10) 0.58245(17) 0.69010(7) 0.0204(4) Uani 1 1 d . . . . .
N5 N 0.32131(10) 0.63576(18) 0.68640(7) 0.0230(4) Uani 1 1 d . . . . .
C1 C 0.54949(19) 0.8953(3) 0.56485(13) 0.0532(9) Uani 1 1 d . . . . .
H1A H 0.586062 0.877487 0.592996 0.080 Uiso 1 1 calc GR . . . .
H1B H 0.544430 0.985208 0.560651 0.080 Uiso 1 1 calc GR . . . .
H1C H 0.567467 0.858904 0.531720 0.080 Uiso 1 1 calc GR . . . .
C2 C 0.47342(15) 0.8406(2) 0.57897(9) 0.0261(5) Uani 1 1 d . . . . .
C3 C 0.50417(11) 0.62389(19) 0.55936(8) 0.0171(4) Uani 1 1 d . . . . .
C4 C 0.47952(11) 0.47565(18) 0.63386(8) 0.0142(4) Uani 1 1 d . . . . .
C5 C 0.48377(12) 0.33070(19) 0.63543(8) 0.0164(4) Uani 1 1 d . . . . .
C6 C 0.56762(13) 0.17389(19) 0.67682(9) 0.0227(5) Uani 1 1 d . . . . .
H6A H 0.529779 0.113900 0.663298 0.027 Uiso 1 1 calc R . . . .
H6B H 0.576399 0.155348 0.714568 0.027 Uiso 1 1 calc R . . . .
C7 C 0.64174(13) 0.1580(2) 0.64669(9) 0.0222(5) Uani 1 1 d . . . . .
C8 C 0.65952(15) 0.2284(2) 0.60316(11) 0.0378(6) Uani 1 1 d . . . . .
H8 H 0.625027 0.290496 0.591628 0.045 Uiso 1 1 calc R . . . .
C9 C 0.72725(17) 0.2103(3) 0.57569(13) 0.0513(8) Uani 1 1 d . . . . .
H9 H 0.738620 0.260229 0.545863 0.062 Uiso 1 1 calc R . . . .
C10 C 0.77706(16) 0.1215(3) 0.59139(12) 0.0482(8) Uani 1 1 d . . . . .
H10 H 0.823485 0.109664 0.572929 0.058 Uiso 1 1 calc R . . . .
C11 C 0.44167(16) 0.8983(2) 0.62902(10) 0.0329(6) Uani 1 1 d . . . . .
H11A H 0.394126 0.856672 0.638614 0.049 Uiso 1 1 calc GR . . . .
H11B H 0.431850 0.986519 0.623031 0.049 Uiso 1 1 calc GR . . . .
H11C H 0.478560 0.888781 0.657700 0.049 Uiso 1 1 calc GR . . . .
C12 C 0.56864(11) 0.40450(19) 0.69655(8) 0.0166(4) Uani 1 1 d . . . . .
C13 C 0.62435(12) 0.4070(2) 0.73513(8) 0.0208(5) Uani 1 1 d . . . . .
H13 H 0.646250 0.332727 0.748257 0.025 Uiso 1 1 calc R . . . .
C14 C 0.64715(12) 0.5224(2) 0.75401(8) 0.0219(5) Uani 1 1 d . . . . .
H14 H 0.685468 0.528002 0.780306 0.026 Uiso 1 1 calc R . . . .
C15 C 0.61374(12) 0.6290(2) 0.73430(8) 0.0190(4) Uani 1 1 d . . . . .
C16 C 0.55717(12) 0.62622(19) 0.69596(8) 0.0181(4) Uani 1 1 d . . . . .
H16 H 0.534339 0.700298 0.683377 0.022 Uiso 1 1 calc R . . . .
C17 C 0.53552(11) 0.51205(19) 0.67693(8) 0.0152(4) Uani 1 1 d . . . . .
C18 C 0.75974(17) 0.0495(3) 0.63390(12) 0.0536(9) Uani 1 1 d . . . . .
H18 H 0.793833 -0.014054 0.644444 0.064 Uiso 1 1 calc R . . . .
C19 C 0.69281(17) 0.0679(3) 0.66208(11) 0.0441(7) Uani 1 1 d . . . . .
H19 H 0.682198 0.018185 0.692103 0.053 Uiso 1 1 calc R . . . .
C20 C 0.29206(12) 0.61163(19) 0.63684(8) 0.0185(4) Uani 1 1 d . . . . .
C21 C 0.22487(12) 0.6545(2) 0.61310(9) 0.0240(5) Uani 1 1 d . . . . .
H21 H 0.190140 0.706054 0.631598 0.029 Uiso 1 1 calc R . . . .
C22 C 0.21173(13) 0.6187(2) 0.56214(9) 0.0273(5) Uani 1 1 d . . . . .
H22 H 0.167489 0.647728 0.544559 0.033 Uiso 1 1 calc R . . . .
C23 C 0.26220(13) 0.5401(2) 0.53523(9) 0.0276(5) Uani 1 1 d . . . . .
H23 H 0.250030 0.515398 0.500272 0.033 Uiso 1 1 calc R . . . .
C24 C 0.32858(13) 0.4974(2) 0.55750(9) 0.0225(5) Uani 1 1 d . . . . .
H24 H 0.362407 0.444355 0.538984 0.027 Uiso 1 1 calc R . . . .
C25 C 0.34323(11) 0.53699(18) 0.60924(8) 0.0155(4) Uani 1 1 d . . . . .
C26 C 0.4148(2) 0.8470(3) 0.53512(11) 0.0509(8) Uani 1 1 d . . . . .
H26A H 0.436355 0.811990 0.502749 0.076 Uiso 1 1 calc GR . . . .
H26B H 0.400603 0.933610 0.528971 0.076 Uiso 1 1 calc GR . . . .
H26C H 0.369656 0.799601 0.545339 0.076 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C15 1.905(2) . ?
O1 C2 1.490(3) . ?
O1 C3 1.333(2) . ?
O2 C5 1.213(2) . ?
O3 C3 1.214(2) . ?
N1 H1 0.8800 . ?
N1 C3 1.372(3) . ?
N1 C4 1.454(3) . ?
N2 C5 1.360(3) . ?
N2 C6 1.459(3) . ?
N2 C12 1.412(3) . ?
N3 N4 1.369(2) . ?
N3 C4 1.470(3) . ?
N3 C25 1.373(3) . ?
N4 N5 1.297(2) . ?
N5 C20 1.383(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.506(4) . ?
C2 C11 1.520(3) . ?
C2 C26 1.518(4) . ?
C4 C5 1.567(3) . ?
C4 C17 1.522(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.521(3) . ?
C7 C8 1.376(4) . ?
C7 C19 1.380(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.394(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.358(4) . ?
C10 H10 0.9500 . ?
C10 C18 1.363(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.385(3) . ?
C12 C17 1.391(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.393(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(3) . ?
C15 C16 1.392(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.377(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.392(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.405(3) . ?
C20 C25 1.396(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.368(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.405(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.377(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.404(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 120.52(16) . . ?
C3 N1 H1 117.2 . . ?
C3 N1 C4 125.50(17) . . ?
C4 N1 H1 117.2 . . ?
C5 N2 C6 123.01(18) . . ?
C5 N2 C12 111.73(17) . . ?
C12 N2 C6 124.30(17) . . ?
N4 N3 C4 119.30(16) . . ?
N4 N3 C25 109.98(16) . . ?
C25 N3 C4 128.88(16) . . ?
N5 N4 N3 109.00(16) . . ?
N4 N5 C20 108.34(17) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 109.0(2) . . ?
O1 C2 C11 102.21(17) . . ?
O1 C2 C26 109.14(19) . . ?
C1 C2 C11 111.4(2) . . ?
C1 C2 C26 114.3(2) . . ?
C26 C2 C11 110.1(2) . . ?
O1 C3 N1 111.42(17) . . ?
O3 C3 O1 126.25(19) . . ?
O3 C3 N1 122.33(19) . . ?
N1 C4 N3 111.18(16) . . ?
N1 C4 C5 104.02(15) . . ?
N1 C4 C17 114.35(16) . . ?
N3 C4 C5 111.72(16) . . ?
N3 C4 C17 112.82(16) . . ?
C17 C4 C5 102.04(16) . . ?
O2 C5 N2 127.84(19) . . ?
O2 C5 C4 124.56(19) . . ?
N2 C5 C4 107.48(17) . . ?
N2 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
N2 C6 C7 112.02(18) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C8 C7 C6 122.4(2) . . ?
C8 C7 C19 117.9(2) . . ?
C19 C7 C6 119.7(2) . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.2(3) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C18 119.3(3) . . ?
C18 C10 H10 120.3 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N2 127.39(19) . . ?
C13 C12 C17 122.18(19) . . ?
C17 C12 N2 110.43(17) . . ?
C12 C13 H13 121.2 . . ?
C12 C13 C14 117.6(2) . . ?
C14 C13 H13 121.2 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 Br1 120.36(16) . . ?
C14 C15 C16 122.5(2) . . ?
C16 C15 Br1 117.10(16) . . ?
C15 C16 H16 121.2 . . ?
C17 C16 C15 117.5(2) . . ?
C17 C16 H16 121.2 . . ?
C12 C17 C4 108.20(17) . . ?
C16 C17 C4 131.39(18) . . ?
C16 C17 C12 120.38(19) . . ?
C10 C18 H18 119.5 . . ?
C10 C18 C19 120.9(3) . . ?
C19 C18 H18 119.5 . . ?
C7 C19 C18 120.4(3) . . ?
C7 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
N5 C20 C21 129.82(19) . . ?
N5 C20 C25 108.91(18) . . ?
C25 C20 C21 121.21(19) . . ?
C20 C21 H21 121.5 . . ?
C22 C21 C20 117.0(2) . . ?
C22 C21 H21 121.5 . . ?
C21 C22 H22 119.3 . . ?
C21 C22 C23 121.5(2) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 118.7 . . ?
C24 C23 C22 122.6(2) . . ?
C24 C23 H23 118.7 . . ?
C23 C24 H24 122.0 . . ?
C23 C24 C25 115.9(2) . . ?
C25 C24 H24 122.0 . . ?
N3 C25 C20 103.75(17) . . ?
N3 C25 C24 134.54(19) . . ?
C20 C25 C24 121.71(19) . . ?
C2 C26 H26A 109.5 . . ?
C2 C26 H26B 109.5 . . ?
C2 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C15 C16 C17 177.46(15) . . . . ?
N1 C4 C5 O2 -60.2(2) . . . . ?
N1 C4 C5 N2 116.21(17) . . . . ?
N1 C4 C17 C12 -108.40(19) . . . . ?
N1 C4 C17 C16 69.5(3) . . . . ?
N2 C6 C7 C8 -26.8(3) . . . . ?
N2 C6 C7 C19 155.1(2) . . . . ?
N2 C12 C13 C14 179.8(2) . . . . ?
N2 C12 C17 C4 -2.4(2) . . . . ?
N2 C12 C17 C16 179.35(18) . . . . ?
N3 N4 N5 C20 -1.2(2) . . . . ?
N3 C4 C5 O2 59.8(3) . . . . ?
N3 C4 C5 N2 -123.77(17) . . . . ?
N3 C4 C17 C12 123.24(18) . . . . ?
N3 C4 C17 C16 -58.8(3) . . . . ?
N4 N3 C4 N1 -133.09(18) . . . . ?
N4 N3 C4 C5 111.19(19) . . . . ?
N4 N3 C4 C17 -3.1(2) . . . . ?
N4 N3 C25 C20 -0.2(2) . . . . ?
N4 N3 C25 C24 179.2(2) . . . . ?
N4 N5 C20 C21 -176.0(2) . . . . ?
N4 N5 C20 C25 1.1(2) . . . . ?
N5 C20 C21 C22 177.5(2) . . . . ?
N5 C20 C25 N3 -0.5(2) . . . . ?
N5 C20 C25 C24 180.0(2) . . . . ?
C2 O1 C3 O3 6.0(3) . . . . ?
C2 O1 C3 N1 -174.19(18) . . . . ?
C3 O1 C2 C1 -69.1(3) . . . . ?
C3 O1 C2 C11 172.93(19) . . . . ?
C3 O1 C2 C26 56.4(3) . . . . ?
C3 N1 C4 N3 54.4(2) . . . . ?
C3 N1 C4 C5 174.78(18) . . . . ?
C3 N1 C4 C17 -74.8(2) . . . . ?
C4 N1 C3 O1 4.7(3) . . . . ?
C4 N1 C3 O3 -175.46(19) . . . . ?
C4 N3 N4 N5 166.78(17) . . . . ?
C4 N3 C25 C20 -164.35(18) . . . . ?
C4 N3 C25 C24 15.0(4) . . . . ?
C5 N2 C6 C7 95.6(2) . . . . ?
C5 N2 C12 C13 -179.7(2) . . . . ?
C5 N2 C12 C17 0.4(2) . . . . ?
C5 C4 C17 C12 3.2(2) . . . . ?
C5 C4 C17 C16 -178.8(2) . . . . ?
C6 N2 C5 O2 8.7(3) . . . . ?
C6 N2 C5 C4 -167.51(18) . . . . ?
C6 N2 C12 C13 -10.6(3) . . . . ?
C6 N2 C12 C17 169.50(19) . . . . ?
C6 C7 C8 C9 -178.8(3) . . . . ?
C6 C7 C19 C18 177.9(3) . . . . ?
C7 C8 C9 C10 0.4(5) . . . . ?
C8 C7 C19 C18 -0.3(4) . . . . ?
C8 C9 C10 C18 0.7(5) . . . . ?
C9 C10 C18 C19 -1.6(5) . . . . ?
C10 C18 C19 C7 1.4(5) . . . . ?
C12 N2 C5 O2 178.0(2) . . . . ?
C12 N2 C5 C4 1.7(2) . . . . ?
C12 N2 C6 C7 -72.3(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C12 C17 C4 177.68(19) . . . . ?
C13 C12 C17 C16 -0.5(3) . . . . ?
C13 C14 C15 Br1 -178.23(16) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C17 -1.1(3) . . . . ?
C15 C16 C17 C4 -176.5(2) . . . . ?
C15 C16 C17 C12 1.2(3) . . . . ?
C17 C4 C5 O2 -179.40(19) . . . . ?
C17 C4 C5 N2 -3.0(2) . . . . ?
C17 C12 C13 C14 -0.3(3) . . . . ?
C19 C7 C8 C9 -0.6(4) . . . . ?
C20 C21 C22 C23 1.6(4) . . . . ?
C21 C20 C25 N3 176.8(2) . . . . ?
C21 C20 C25 C24 -2.6(3) . . . . ?
C21 C22 C23 C24 -2.0(4) . . . . ?
C22 C23 C24 C25 0.1(3) . . . . ?
C23 C24 C25 N3 -177.1(2) . . . . ?
C23 C24 C25 C20 2.1(3) . . . . ?
C25 N3 N4 N5 0.9(2) . . . . ?
C25 N3 C4 N1 29.8(3) . . . . ?
C25 N3 C4 C5 -85.9(2) . . . . ?
C25 N3 C4 C17 159.84(19) . . . . ?
C25 C20 C21 C22 0.7(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_mo_cxy0417_0m
_database_code_depnum_ccdc_archive 'CCDC 1903689'
loop_
_audit_author_name
_audit_author_address
'Pengfei Li' 'Southern University of Science and Technology'
_audit_update_record             
;
2019-03-18 deposited with the CCDC.	2019-08-28 downloaded from the CCDC.
;
_audit_creation_date             2018-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 Br N5 O3'
_chemical_formula_sum            'C23 H24 Br N5 O3'
_chemical_formula_weight         498.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.5473(9)
_cell_length_b                   10.6285(4)
_cell_length_c                   22.3229(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.4750(10)
_cell_angle_gamma                90
_cell_volume                     4623.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   0.631
_shelx_estimated_absorpt_T_min   0.570
_exptl_absorpt_coefficient_mu    1.812
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0884 before and 0.0556 after correction. The Ratio of minimum to maximum transmission is 0.6531. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24501
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         2.248
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_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                4376
_reflns_number_total             5306
_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       ?
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.034
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.00100(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.027
_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)+(0.0295P)²+6.3331P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0812
_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.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C9(H9), C10(H10), C12(H12), C16(H16), C17(H17), C19(H19),
 C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C23(H23A,H23B,H23C)
;
_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 0.07782(2) 0.82426(2) 0.30760(2) 0.03432(9) Uani 1 1 d . . . . .
O1 O 0.48989(7) 0.90542(12) 0.42254(6) 0.0217(3) Uani 1 1 d . . . . .
O2 O 0.42134(7) 0.55858(14) 0.31981(7) 0.0302(3) Uani 1 1 d . . . . .
O3 O 0.38760(7) 0.87345(12) 0.34467(6) 0.0249(3) Uani 1 1 d . . . . .
N1 N 0.42926(8) 0.73806(14) 0.42703(7) 0.0178(3) Uani 1 1 d . . . . .
H1 H 0.4599 0.7259 0.4643 0.021 Uiso 1 1 calc R . . . .
N2 N 0.30607(8) 0.60158(14) 0.29691(7) 0.0211(3) Uani 1 1 d . . . . .
N3 N 0.39186(7) 0.53774(13) 0.44383(7) 0.0168(3) Uani 1 1 d . . . . .
N4 N 0.44173(8) 0.37009(14) 0.49408(8) 0.0221(3) Uani 1 1 d . . . . .
N5 N 0.37570(8) 0.53737(14) 0.49888(7) 0.0200(3) Uani 1 1 d . . . . .
C1 C 0.58108(11) 1.0452(2) 0.43960(10) 0.0332(5) Uani 1 1 d . . . . .
H1A H 0.5769 1.0593 0.4816 0.050 Uiso 1 1 calc GR . . . .
H1B H 0.5998 1.1208 0.4260 0.050 Uiso 1 1 calc GR . . . .
H1C H 0.6119 0.9740 0.4413 0.050 Uiso 1 1 calc GR . . . .
C2 C 0.51089(10) 1.01639(17) 0.39300(9) 0.0213(4) Uani 1 1 d . . . . .
C3 C 0.43178(9) 0.84352(16) 0.39297(8) 0.0177(4) Uani 1 1 d . . . . .
C4 C 0.37585(9) 0.64686(16) 0.40123(8) 0.0164(4) Uani 1 1 d . . . . .
C5 C 0.37292(10) 0.59686(17) 0.33426(9) 0.0208(4) Uani 1 1 d . . . . .
C6 C 0.28262(11) 0.55368(18) 0.23222(9) 0.0270(4) Uani 1 1 d . . . . .
H6A H 0.2396 0.5058 0.2258 0.032 Uiso 1 1 calc R . . . .
H6B H 0.3174 0.4945 0.2266 0.032 Uiso 1 1 calc R . . . .
C7 C 0.26990(10) 0.65504(17) 0.18222(9) 0.0221(4) Uani 1 1 d . . . . .
C8 C 0.30341(11) 0.77001(19) 0.19362(9) 0.0271(4) Uani 1 1 d . . . . .
H8 H 0.3339 0.7887 0.2345 0.032 Uiso 1 1 calc R . . . .
C9 C 0.29247(12) 0.8582(2) 0.14535(10) 0.0311(5) Uani 1 1 d . . . . .
H9 H 0.3151 0.9372 0.1535 0.037 Uiso 1 1 calc R . . . .
C10 C 0.24875(12) 0.8311(2) 0.08559(10) 0.0344(5) Uani 1 1 d . . . . .
H10 H 0.2419 0.8910 0.0526 0.041 Uiso 1 1 calc R . . . .
C11 C 0.46108(13) 1.1230(2) 0.38912(12) 0.0366(5) Uani 1 1 d . . . . .
H11A H 0.4159 1.0998 0.3602 0.055 Uiso 1 1 calc GR . . . .
H11B H 0.4775 1.1988 0.3734 0.055 Uiso 1 1 calc GR . . . .
H11C H 0.4576 1.1395 0.4312 0.055 Uiso 1 1 calc GR . . . .
C12 C 0.43164(9) 0.43807(17) 0.44274(9) 0.0216(4) Uani 1 1 d . . . . .
H12 H 0.4499 0.4194 0.4096 0.026 Uiso 1 1 calc R . . . .
C13 C 0.40637(9) 0.43396(17) 0.52706(9) 0.0201(4) Uani 1 1 d . . . . .
C14 C 0.40215(11) 0.3876(2) 0.58876(10) 0.0295(5) Uani 1 1 d . . . . .
H14A H 0.4472 0.3955 0.6211 0.044 Uiso 1 1 calc GR . . . .
H14B H 0.3880 0.2991 0.5847 0.044 Uiso 1 1 calc GR . . . .
H14C H 0.3685 0.4377 0.6011 0.044 Uiso 1 1 calc GR . . . .
C15 C 0.30358(9) 0.69366(16) 0.38927(8) 0.0164(4) Uani 1 1 d . . . . .
C16 C 0.27485(9) 0.76058(17) 0.42723(8) 0.0187(4) Uani 1 1 d . . . . .
H16 H 0.3012 0.7808 0.4694 0.022 Uiso 1 1 calc R . . . .
C17 C 0.20649(10) 0.79833(17) 0.40296(9) 0.0216(4) Uani 1 1 d . . . . .
H17 H 0.1854 0.8440 0.4284 0.026 Uiso 1 1 calc R . . . .
C18 C 0.16994(9) 0.76800(17) 0.34105(9) 0.0213(4) Uani 1 1 d . . . . .
C19 C 0.19750(10) 0.70099(17) 0.30145(9) 0.0225(4) Uani 1 1 d . . . . .
H19 H 0.1714 0.6811 0.2592 0.027 Uiso 1 1 calc R . . . .
C20 C 0.26521(10) 0.66494(16) 0.32723(8) 0.0185(4) Uani 1 1 d . . . . .
C21 C 0.22535(10) 0.6290(2) 0.12193(9) 0.0280(4) Uani 1 1 d . . . . .
H21 H 0.2019 0.5507 0.1137 0.034 Uiso 1 1 calc R . . . .
C22 C 0.21514(11) 0.7171(2) 0.07404(10) 0.0361(5) Uani 1 1 d . . . . .
H22 H 0.1848 0.6988 0.0330 0.043 Uiso 1 1 calc R . . . .
C23 C 0.51662(12) 0.9793(2) 0.32949(10) 0.0313(5) Uani 1 1 d . . . . .
H23A H 0.5443 0.9027 0.3341 0.047 Uiso 1 1 calc GR . . . .
H23B H 0.5385 1.0475 0.3134 0.047 Uiso 1 1 calc GR . . . .
H23C H 0.4707 0.9637 0.2998 0.047 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C18 1.8979(18) . ?
O1 C2 1.481(2) . ?
O1 C3 1.340(2) . ?
O2 C5 1.210(2) . ?
O3 C3 1.211(2) . ?
N1 H1 0.8800 . ?
N1 C3 1.365(2) . ?
N1 C4 1.441(2) . ?
N2 C5 1.363(2) . ?
N2 C6 1.461(2) . ?
N2 C20 1.406(2) . ?
N3 N5 1.371(2) . ?
N3 C4 1.469(2) . ?
N3 C12 1.343(2) . ?
N4 C12 1.315(2) . ?
N4 C13 1.367(3) . ?
N5 C13 1.323(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.518(3) . ?
C2 C11 1.511(3) . ?
C2 C23 1.512(3) . ?
C4 C5 1.570(3) . ?
C4 C15 1.507(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.513(3) . ?
C7 C8 1.386(3) . ?
C7 C21 1.395(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.391(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.382(3) . ?
C10 H10 0.9500 . ?
C10 C22 1.378(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 0.9500 . ?
C13 C14 1.491(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.374(3) . ?
C15 C20 1.393(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.395(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(3) . ?
C18 C19 1.388(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.381(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(3) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 120.78(14) . . ?
C3 N1 H1 120.4 . . ?
C3 N1 C4 119.25(15) . . ?
C4 N1 H1 120.4 . . ?
C5 N2 C6 122.98(17) . . ?
C5 N2 C20 111.27(15) . . ?
C20 N2 C6 125.62(16) . . ?
N5 N3 C4 120.95(14) . . ?
C12 N3 N5 109.62(15) . . ?
C12 N3 C4 128.58(16) . . ?
C12 N4 C13 103.46(15) . . ?
C13 N5 N3 102.38(15) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 101.71(15) . . ?
O1 C2 C11 109.59(16) . . ?
O1 C2 C23 109.30(15) . . ?
C11 C2 C1 111.56(18) . . ?
C11 C2 C23 113.23(18) . . ?
C23 C2 C1 110.83(17) . . ?
O1 C3 N1 108.31(15) . . ?
O3 C3 O1 127.52(16) . . ?
O3 C3 N1 124.17(17) . . ?
N1 C4 N3 106.64(14) . . ?
N1 C4 C5 113.77(15) . . ?
N1 C4 C15 115.57(14) . . ?
N3 C4 C5 106.40(13) . . ?
N3 C4 C15 112.40(14) . . ?
C15 C4 C5 101.82(14) . . ?
O2 C5 N2 127.13(18) . . ?
O2 C5 C4 125.55(17) . . ?
N2 C5 C4 107.29(15) . . ?
N2 C6 H6A 108.8 . . ?
N2 C6 H6B 108.8 . . ?
N2 C6 C7 113.99(15) . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C8 C7 C6 122.19(17) . . ?
C8 C7 C21 119.20(18) . . ?
C21 C7 C6 118.54(18) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.18(19) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.1 . . ?
C22 C10 C9 119.8(2) . . ?
C22 C10 H10 120.1 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 H12 124.9 . . ?
N4 C12 N3 110.27(17) . . ?
N4 C12 H12 124.9 . . ?
N4 C13 C14 121.98(17) . . ?
N5 C13 N4 114.27(16) . . ?
N5 C13 C14 123.74(18) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C4 130.77(16) . . ?
C16 C15 C20 120.53(17) . . ?
C20 C15 C4 108.60(16) . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 119.07(17) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 120.6 . . ?
C18 C17 C16 118.77(18) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 Br1 118.48(15) . . ?
C17 C18 C19 123.57(17) . . ?
C19 C18 Br1 117.93(14) . . ?
C18 C19 H19 122.0 . . ?
C20 C19 C18 115.96(17) . . ?
C20 C19 H19 122.0 . . ?
C15 C20 N2 110.34(16) . . ?
C19 C20 N2 127.51(17) . . ?
C19 C20 C15 122.10(18) . . ?
C7 C21 H21 119.9 . . ?
C22 C21 C7 120.2(2) . . ?
C22 C21 H21 119.9 . . ?
C10 C22 C21 120.3(2) . . ?
C10 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C2 C23 H23A 109.5 . . ?
C2 C23 H23B 109.5 . . ?
C2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C18 C19 C20 178.28(13) . . . . ?
N1 C4 C5 O2 49.0(2) . . . . ?
N1 C4 C5 N2 -132.67(15) . . . . ?
N1 C4 C15 C16 -48.2(3) . . . . ?
N1 C4 C15 C20 128.02(16) . . . . ?
N2 C6 C7 C8 26.1(3) . . . . ?
N2 C6 C7 C21 -156.94(18) . . . . ?
N3 N5 C13 N4 1.0(2) . . . . ?
N3 N5 C13 C14 -177.64(17) . . . . ?
N3 C4 C5 O2 -68.1(2) . . . . ?
N3 C4 C5 N2 110.22(16) . . . . ?
N3 C4 C15 C16 74.5(2) . . . . ?
N3 C4 C15 C20 -109.26(16) . . . . ?
N5 N3 C4 N1 80.65(19) . . . . ?
N5 N3 C4 C5 -157.59(15) . . . . ?
N5 N3 C4 C15 -47.0(2) . . . . ?
N5 N3 C12 N4 1.1(2) . . . . ?
C2 O1 C3 O3 -7.6(3) . . . . ?
C2 O1 C3 N1 172.99(15) . . . . ?
C3 O1 C2 C1 -174.61(16) . . . . ?
C3 O1 C2 C11 67.2(2) . . . . ?
C3 O1 C2 C23 -57.4(2) . . . . ?
C3 N1 C4 N3 172.43(15) . . . . ?
C3 N1 C4 C5 55.5(2) . . . . ?
C3 N1 C4 C15 -61.8(2) . . . . ?
C4 N1 C3 O1 -172.42(15) . . . . ?
C4 N1 C3 O3 8.2(3) . . . . ?
C4 N3 N5 C13 -171.52(15) . . . . ?
C4 N3 C12 N4 170.41(16) . . . . ?
C4 C15 C16 C17 176.52(17) . . . . ?
C4 C15 C20 N2 0.50(19) . . . . ?
C4 C15 C20 C19 -177.15(16) . . . . ?
C5 N2 C6 C7 -102.1(2) . . . . ?
C5 N2 C20 C15 -6.0(2) . . . . ?
C5 N2 C20 C19 171.52(18) . . . . ?
C5 C4 C15 C16 -172.06(18) . . . . ?
C5 C4 C15 C20 4.21(18) . . . . ?
C6 N2 C5 O2 2.8(3) . . . . ?
C6 N2 C5 C4 -175.41(15) . . . . ?
C6 N2 C20 C15 178.08(16) . . . . ?
C6 N2 C20 C19 -4.4(3) . . . . ?
C6 C7 C8 C9 177.01(19) . . . . ?
C6 C7 C21 C22 -176.69(19) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C7 C21 C22 C10 -0.1(3) . . . . ?
C8 C7 C21 C22 0.3(3) . . . . ?
C8 C9 C10 C22 0.9(3) . . . . ?
C9 C10 C22 C21 -0.5(3) . . . . ?
C12 N3 N5 C13 -1.25(19) . . . . ?
C12 N3 C4 N1 -87.6(2) . . . . ?
C12 N3 C4 C5 34.2(2) . . . . ?
C12 N3 C4 C15 144.79(18) . . . . ?
C12 N4 C13 N5 -0.4(2) . . . . ?
C12 N4 C13 C14 178.28(17) . . . . ?
C13 N4 C12 N3 -0.4(2) . . . . ?
C15 C4 C5 O2 174.07(18) . . . . ?
C15 C4 C5 N2 -7.64(18) . . . . ?
C15 C16 C17 C18 -0.6(3) . . . . ?
C16 C15 C20 N2 177.22(15) . . . . ?
C16 C15 C20 C19 -0.4(3) . . . . ?
C16 C17 C18 Br1 -178.06(13) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C19 C20 N2 -177.04(17) . . . . ?
C18 C19 C20 C15 0.2(3) . . . . ?
C20 N2 C5 O2 -173.23(18) . . . . ?
C20 N2 C5 C4 8.52(19) . . . . ?
C20 N2 C6 C7 73.4(2) . . . . ?
C20 C15 C16 C17 0.6(3) . . . . ?
C21 C7 C8 C9 0.1(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_cxy0769_0m
_database_code_depnum_ccdc_archive 'CCDC 1919350'
loop_
_audit_author_name
_audit_author_address
'Pengfei Li' 'Southern University of Science and Technology'
_audit_update_record             
;
2019-05-29 deposited with the CCDC.	2019-08-28 downloaded from the CCDC.
;
_audit_creation_date             2019-05-24
_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         'C26 H26 Cl N3 O3'
_chemical_formula_sum            'C26 H26 Cl N3 O3'
_chemical_formula_weight         463.95
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   11.1047(6)
_cell_length_b                   9.5460(5)
_cell_length_c                   22.3027(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.1790(10)
_cell_angle_gamma                90
_cell_volume                     2311.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.56
_cell_measurement_theta_min      4.07
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.735
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0592 before and 0.0439 after correction. The Ratio of minimum to maximum transmission is 0.9209. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.29
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            25207
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.559
_diffrn_reflns_theta_min         4.072
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4120
_reflns_number_total             4249
_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       ?
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0088(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.051
_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)+(0.0328P)²+1.3855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0789
_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.a Riding coordinates:
 N2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C1(H1), C2(H2A), C3(H3A), C9(H9), C10(H10), C11(H11), C17(H17),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C26(H26A,H26B,H26C)
;
_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
Cl1 Cl 0.29660(3) 0.84487(4) 0.40585(2) 0.02334(11) Uani 1 1 d . . . . .
O1 O 0.96073(7) 0.59195(9) 0.62259(4) 0.0135(2) Uani 1 1 d . . . . .
O2 O 0.75487(8) 0.57721(10) 0.57994(4) 0.0177(2) Uani 1 1 d . . . . .
O3 O 0.83223(8) 0.36183(9) 0.46773(4) 0.0160(2) Uani 1 1 d . . . . .
N1 N 0.64018(9) 0.46353(11) 0.43957(5) 0.0125(2) Uani 1 1 d . . . . .
N2 N 0.86432(9) 0.64326(11) 0.41280(5) 0.0129(2) Uani 1 1 d . . . . .
H2 H 0.930165 0.591121 0.414092 0.015 Uiso 1 1 d R . . . .
N3 N 0.89474(9) 0.64209(11) 0.52393(5) 0.0125(2) Uani 1 1 d . . . . .
H3 H 0.966975 0.681124 0.525071 0.015 Uiso 1 1 calc R . . . .
C1 C 0.49570(14) 0.17830(16) 0.24277(6) 0.0253(3) Uani 1 1 d . . . . .
H1 H 0.480393 0.140476 0.202477 0.030 Uiso 1 1 calc R . . . .
C2 C 0.59043(13) 0.27377(15) 0.26111(6) 0.0229(3) Uani 1 1 d . . . . .
H2A H 0.639476 0.302318 0.233170 0.028 Uiso 1 1 calc R . . . .
C3 C 0.61378(12) 0.32785(14) 0.32041(6) 0.0185(3) Uani 1 1 d . . . . .
H3A H 0.679000 0.392930 0.332817 0.022 Uiso 1 1 calc R . . . .
C4 C 0.54229(11) 0.28723(13) 0.36156(6) 0.0138(3) Uani 1 1 d . . . . .
C5 C 0.56823(11) 0.33503(13) 0.42779(6) 0.0142(3) Uani 1 1 d . . . . .
H5A H 0.488745 0.349424 0.440321 0.017 Uiso 1 1 calc R . . . .
H5B H 0.612874 0.259485 0.453755 0.017 Uiso 1 1 calc R . . . .
C6 C 0.76495(11) 0.46435(13) 0.45901(5) 0.0125(3) Uani 1 1 d . . . . .
C7 C 0.80842(11) 0.61900(13) 0.46563(5) 0.0119(3) Uani 1 1 d . . . . .
C8 C 0.88608(11) 0.78764(13) 0.39939(5) 0.0132(3) Uani 1 1 d . . . . .
C9 C 0.79385(12) 0.85819(14) 0.35859(6) 0.0162(3) Uani 1 1 d . . . . .
H9 H 0.723157 0.808692 0.337694 0.019 Uiso 1 1 calc R . . . .
C10 C 0.80475(13) 1.00049(15) 0.34833(6) 0.0202(3) Uani 1 1 d . . . . .
H10 H 0.740521 1.048831 0.321362 0.024 Uiso 1 1 calc R . . . .
C11 C 0.90951(14) 1.07219(14) 0.37747(6) 0.0230(3) Uani 1 1 d . . . . .
H11 H 0.916339 1.170082 0.371274 0.028 Uiso 1 1 calc R . . . .
C12 C 1.07984(12) 0.56877(14) 0.72205(6) 0.0191(3) Uani 1 1 d . . . . .
H12A H 1.125391 0.493695 0.706666 0.029 Uiso 1 1 calc GR . . . .
H12B H 1.082079 0.553615 0.765730 0.029 Uiso 1 1 calc GR . . . .
H12C H 1.117784 0.659249 0.716541 0.029 Uiso 1 1 calc GR . . . .
C13 C 0.94666(12) 0.56840(13) 0.68664(5) 0.0153(3) Uani 1 1 d . . . . .
C14 C 0.87465(13) 0.68924(15) 0.70607(6) 0.0210(3) Uani 1 1 d . . . . .
H14A H 0.909867 0.778150 0.696035 0.031 Uiso 1 1 calc GR . . . .
H14B H 0.879219 0.684346 0.750385 0.031 Uiso 1 1 calc GR . . . .
H14C H 0.788361 0.683234 0.684334 0.031 Uiso 1 1 calc GR . . . .
C15 C 0.86057(11) 0.60164(13) 0.57653(6) 0.0127(2) Uani 1 1 d . . . . .
C16 C 0.59205(11) 0.60055(13) 0.43835(5) 0.0121(2) Uani 1 1 d . . . . .
C17 C 0.47012(11) 0.64145(13) 0.42201(6) 0.0145(3) Uani 1 1 d . . . . .
H17 H 0.405338 0.576185 0.408889 0.017 Uiso 1 1 calc R . . . .
C18 C 0.44826(11) 0.78493(14) 0.42603(6) 0.0156(3) Uani 1 1 d . . . . .
C19 C 0.54036(12) 0.88183(14) 0.44635(6) 0.0157(3) Uani 1 1 d . . . . .
H19 H 0.520820 0.978208 0.449030 0.019 Uiso 1 1 calc R . . . .
C20 C 0.66247(12) 0.83644(13) 0.46290(6) 0.0142(3) Uani 1 1 d . . . . .
H20 H 0.727021 0.901096 0.477519 0.017 Uiso 1 1 calc R . . . .
C21 C 0.68754(11) 0.69616(13) 0.45762(5) 0.0118(2) Uani 1 1 d . . . . .
C22 C 0.42346(13) 0.13830(15) 0.28346(7) 0.0252(3) Uani 1 1 d . . . . .
H22 H 0.358055 0.073542 0.270847 0.030 Uiso 1 1 calc R . . . .
C23 C 0.44619(12) 0.19238(14) 0.34254(6) 0.0191(3) Uani 1 1 d . . . . .
H23 H 0.396115 0.164729 0.370154 0.023 Uiso 1 1 calc R . . . .
C24 C 1.00413(13) 1.00046(15) 0.41563(7) 0.0235(3) Uani 1 1 d . . . . .
H24 H 1.077460 1.048706 0.434027 0.028 Uiso 1 1 calc R . . . .
C25 C 0.99272(12) 0.85842(14) 0.42726(6) 0.0179(3) Uani 1 1 d . . . . .
H25 H 1.057294 0.810127 0.454027 0.022 Uiso 1 1 calc R . . . .
C26 C 0.88722(13) 0.42700(14) 0.69229(6) 0.0207(3) Uani 1 1 d . . . . .
H26A H 0.801264 0.429046 0.669851 0.031 Uiso 1 1 calc GR . . . .
H26B H 0.890105 0.406675 0.735641 0.031 Uiso 1 1 calc GR . . . .
H26C H 0.931958 0.354085 0.675021 0.031 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C18 1.7454(12) . ?
O1 C13 1.4867(14) . ?
O1 C15 1.3486(14) . ?
O2 C15 1.2147(15) . ?
O3 C6 1.2217(15) . ?
N1 C5 1.4572(15) . ?
N1 C6 1.3617(16) . ?
N1 C16 1.4111(16) . ?
N2 H2 0.8800 . ?
N2 C7 1.4615(15) . ?
N2 C8 1.4415(16) . ?
N3 H3 0.8800 . ?
N3 C7 1.4601(15) . ?
N3 C15 1.3627(16) . ?
C1 H1 0.9500 . ?
C1 C2 1.387(2) . ?
C1 C22 1.386(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.3921(19) . ?
C3 H3A 0.9500 . ?
C3 C4 1.3892(18) . ?
C4 C5 1.5145(17) . ?
C4 C23 1.3956(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5505(16) . ?
C7 C21 1.5084(16) . ?
C8 C9 1.3918(18) . ?
C8 C25 1.3909(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.3870(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(2) . ?
C11 H11 0.9500 . ?
C11 C24 1.386(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 C13 1.5226(17) . ?
C13 C14 1.5179(18) . ?
C13 C26 1.5193(18) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 C17 1.3821(17) . ?
C16 C21 1.3964(17) . ?
C17 H17 0.9500 . ?
C17 C18 1.3972(18) . ?
C18 C19 1.3825(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.3969(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.3778(18) . ?
C22 H22 0.9500 . ?
C22 C23 1.388(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.3913(19) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 C13 120.35(9) . . ?
C6 N1 C5 123.00(10) . . ?
C6 N1 C16 110.89(10) . . ?
C16 N1 C5 125.86(10) . . ?
C7 N2 H2 112.0 . . ?
C8 N2 H2 111.9 . . ?
C8 N2 C7 115.92(9) . . ?
C7 N3 H3 120.9 . . ?
C15 N3 H3 120.9 . . ?
C15 N3 C7 118.30(10) . . ?
C2 C1 H1 120.1 . . ?
C22 C1 H1 120.1 . . ?
C22 C1 C2 119.73(13) . . ?
C1 C2 H2A 119.9 . . ?
C1 C2 C3 120.10(13) . . ?
C3 C2 H2A 119.9 . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 C2 120.41(13) . . ?
C4 C3 H3A 119.8 . . ?
C3 C4 C5 122.86(11) . . ?
C3 C4 C23 119.16(12) . . ?
C23 C4 C5 117.88(11) . . ?
N1 C5 C4 114.44(10) . . ?
N1 C5 H5A 108.7 . . ?
N1 C5 H5B 108.7 . . ?
C4 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
O3 C6 N1 126.37(11) . . ?
O3 C6 C7 125.44(11) . . ?
N1 C6 C7 108.14(10) . . ?
N2 C7 C6 104.52(9) . . ?
N2 C7 C21 110.23(10) . . ?
N3 C7 N2 112.54(10) . . ?
N3 C7 C6 111.18(10) . . ?
N3 C7 C21 115.62(10) . . ?
C21 C7 C6 101.67(9) . . ?
C9 C8 N2 117.77(11) . . ?
C25 C8 N2 122.41(11) . . ?
C25 C8 C9 119.78(12) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.27(12) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 119.97(13) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.1 . . ?
C24 C11 C10 119.74(13) . . ?
C24 C11 H11 120.1 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
O1 C13 C12 102.15(9) . . ?
O1 C13 C14 109.14(10) . . ?
O1 C13 C26 110.46(10) . . ?
C14 C13 C12 111.27(11) . . ?
C14 C13 C26 112.78(11) . . ?
C26 C13 C12 110.52(11) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 N3 109.90(10) . . ?
O2 C15 O1 126.28(11) . . ?
O2 C15 N3 123.81(11) . . ?
C17 C16 N1 127.80(11) . . ?
C17 C16 C21 122.32(12) . . ?
C21 C16 N1 109.88(10) . . ?
C16 C17 H17 122.1 . . ?
C16 C17 C18 115.71(11) . . ?
C18 C17 H17 122.1 . . ?
C17 C18 Cl1 118.43(10) . . ?
C19 C18 Cl1 118.16(10) . . ?
C19 C18 C17 123.40(12) . . ?
C18 C19 H19 120.4 . . ?
C18 C19 C20 119.26(12) . . ?
C20 C19 H19 120.4 . . ?
C19 C20 H20 120.6 . . ?
C21 C20 C19 118.77(12) . . ?
C21 C20 H20 120.6 . . ?
C16 C21 C7 108.44(10) . . ?
C20 C21 C7 130.94(11) . . ?
C20 C21 C16 120.50(11) . . ?
C1 C22 H22 119.8 . . ?
C1 C22 C23 120.32(13) . . ?
C23 C22 H22 119.8 . . ?
C4 C23 H23 119.9 . . ?
C22 C23 C4 120.27(13) . . ?
C22 C23 H23 119.9 . . ?
C11 C24 H24 119.7 . . ?
C11 C24 C25 120.60(13) . . ?
C25 C24 H24 119.7 . . ?
C8 C25 C24 119.51(12) . . ?
C8 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C13 C26 H26A 109.5 . . ?
C13 C26 H26B 109.5 . . ?
C13 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C18 C19 C20 179.87(9) . . . . ?
O3 C6 C7 N2 72.31(14) . . . . ?
O3 C6 C7 N3 -49.36(16) . . . . ?
O3 C6 C7 C21 -172.97(11) . . . . ?
N1 C6 C7 N2 -105.30(10) . . . . ?
N1 C6 C7 N3 133.03(10) . . . . ?
N1 C6 C7 C21 9.42(12) . . . . ?
N1 C16 C17 C18 178.93(11) . . . . ?
N1 C16 C21 C7 6.46(13) . . . . ?
N1 C16 C21 C20 -177.06(11) . . . . ?
N2 C7 C21 C16 101.02(11) . . . . ?
N2 C7 C21 C20 -74.96(16) . . . . ?
N2 C8 C9 C10 174.01(11) . . . . ?
N2 C8 C25 C24 -175.38(12) . . . . ?
N3 C7 C21 C16 -129.94(11) . . . . ?
N3 C7 C21 C20 54.07(17) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C1 C22 C23 C4 -0.2(2) . . . . ?
C2 C1 C22 C23 -0.6(2) . . . . ?
C2 C3 C4 C5 175.95(12) . . . . ?
C2 C3 C4 C23 -0.50(19) . . . . ?
C3 C4 C5 N1 22.15(17) . . . . ?
C3 C4 C23 C22 0.73(19) . . . . ?
C5 N1 C6 O3 1.69(19) . . . . ?
C5 N1 C6 C7 179.28(10) . . . . ?
C5 N1 C16 C17 -4.79(19) . . . . ?
C5 N1 C16 C21 174.29(10) . . . . ?
C5 C4 C23 C22 -175.89(12) . . . . ?
C6 N1 C5 C4 -94.38(14) . . . . ?
C6 N1 C16 C17 -179.13(12) . . . . ?
C6 N1 C16 C21 -0.05(13) . . . . ?
C6 C7 C21 C16 -9.40(12) . . . . ?
C6 C7 C21 C20 174.61(12) . . . . ?
C7 N2 C8 C9 -91.52(13) . . . . ?
C7 N2 C8 C25 86.14(14) . . . . ?
C7 N3 C15 O1 162.03(10) . . . . ?
C7 N3 C15 O2 -17.28(18) . . . . ?
C8 N2 C7 N3 -73.61(13) . . . . ?
C8 N2 C7 C6 165.62(10) . . . . ?
C8 N2 C7 C21 57.08(13) . . . . ?
C8 C9 C10 C11 1.83(19) . . . . ?
C9 C8 C25 C24 2.23(19) . . . . ?
C9 C10 C11 C24 1.5(2) . . . . ?
C10 C11 C24 C25 -3.0(2) . . . . ?
C11 C24 C25 C8 1.1(2) . . . . ?
C13 O1 C15 O2 -9.02(18) . . . . ?
C13 O1 C15 N3 171.69(10) . . . . ?
C15 O1 C13 C12 -178.50(10) . . . . ?
C15 O1 C13 C14 -60.63(14) . . . . ?
C15 O1 C13 C26 63.91(14) . . . . ?
C15 N3 C7 N2 -169.64(10) . . . . ?
C15 N3 C7 C6 -52.77(14) . . . . ?
C15 N3 C7 C21 62.46(14) . . . . ?
C16 N1 C5 C4 91.93(14) . . . . ?
C16 N1 C6 O3 176.22(11) . . . . ?
C16 N1 C6 C7 -6.19(13) . . . . ?
C16 C17 C18 Cl1 179.74(9) . . . . ?
C16 C17 C18 C19 -1.60(18) . . . . ?
C17 C16 C21 C7 -174.41(11) . . . . ?
C17 C16 C21 C20 2.07(18) . . . . ?
C17 C18 C19 C20 1.20(19) . . . . ?
C18 C19 C20 C21 0.88(18) . . . . ?
C19 C20 C21 C7 173.12(12) . . . . ?
C19 C20 C21 C16 -2.46(18) . . . . ?
C21 C16 C17 C18 -0.04(17) . . . . ?
C22 C1 C2 C3 0.8(2) . . . . ?
C23 C4 C5 N1 -161.35(11) . . . . ?
C25 C8 C9 C10 -3.71(19) . . . . ?

_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_cxy0590_0m
_database_code_depnum_ccdc_archive 'CCDC 1919369'
loop_
_audit_author_name
_audit_author_address
'Pengfei Li' 'Southern University of Science and Technology'
_audit_update_record             
;
2019-05-29 deposited with the CCDC.	2019-08-28 downloaded from the CCDC.
;
_audit_creation_date             2018-12-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H28 Br N3 O3'
_chemical_formula_sum            'C30 H28 Br N3 O3'
_chemical_formula_weight         558.46
_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                   9.7016(6)
_cell_length_b                   11.8988(7)
_cell_length_c                   12.2186(7)
_cell_angle_alpha                65.813(2)
_cell_angle_beta                 85.063(2)
_cell_angle_gamma                89.505(2)
_cell_volume                     1281.34(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   0.574
_shelx_estimated_absorpt_T_min   0.525
_exptl_absorpt_coefficient_mu    1.642
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0817 before and 0.0541 after correction. The Ratio of minimum to maximum transmission is 0.8220. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.38
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23597
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.552
_diffrn_reflns_theta_min         2.667
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_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                5369
_reflns_number_total             5923
_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       ?
_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         0.346
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         5923
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      1.041
_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)+(0.0240P)²+0.7072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0684
_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.a Riding coordinates:
 N2(H2), N3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3A), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C30(H30)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_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 -0.12343(2) 0.91568(2) 0.31611(2) 0.01748(6) Uani 1 1 d . . . . .
O1 O 0.37317(11) 0.40262(10) 0.58679(10) 0.0142(2) Uani 1 1 d . . . . .
O2 O 0.07827(12) 0.41905(10) 0.76459(10) 0.0172(2) Uani 1 1 d . . . . .
O3 O 0.20618(11) 0.35068(10) 0.92723(9) 0.0151(2) Uani 1 1 d . . . . .
N1 N 0.21857(13) 0.54054(11) 0.47435(11) 0.0111(2) Uani 1 1 d . . . . .
N2 N 0.43580(13) 0.64246(12) 0.59991(11) 0.0123(3) Uani 1 1 d . . . . .
H2 H 0.485223 0.631308 0.548612 0.015 Uiso 1 1 d R . . . .
N3 N 0.28463(13) 0.50988(11) 0.76263(11) 0.0113(2) Uani 1 1 d . . . . .
H3 H 0.357115 0.492593 0.793533 0.014 Uiso 1 1 d R . . . .
C1 C 0.42232(18) 0.61153(16) 0.05093(14) 0.0203(4) Uani 1 1 d . . . . .
H1 H 0.473855 0.639213 -0.025587 0.024 Uiso 1 1 calc R . . . .
C2 C 0.32425(18) 0.51735(17) 0.08460(15) 0.0228(4) Uani 1 1 d . . . . .
H2A H 0.308064 0.480420 0.030945 0.027 Uiso 1 1 calc R . . . .
C3 C 0.24927(18) 0.47641(16) 0.19625(15) 0.0192(3) Uani 1 1 d . . . . .
H3A H 0.181444 0.411915 0.218645 0.023 Uiso 1 1 calc R . . . .
C4 C 0.27299(16) 0.52951(14) 0.27595(13) 0.0117(3) Uani 1 1 d . . . . .
C5 C 0.18943(16) 0.47941(14) 0.39682(13) 0.0125(3) Uani 1 1 d . . . . .
H5A H 0.089894 0.487040 0.383612 0.015 Uiso 1 1 calc R . . . .
H5B H 0.207533 0.390563 0.439084 0.015 Uiso 1 1 calc R . . . .
C6 C 0.30386(15) 0.49368(13) 0.56403(13) 0.0108(3) Uani 1 1 d . . . . .
C7 C 0.30161(15) 0.57989(13) 0.63236(13) 0.0105(3) Uani 1 1 d . . . . .
C8 C 0.47294(15) 0.74163(13) 0.62553(13) 0.0112(3) Uani 1 1 d . . . . .
C9 C 0.40868(16) 0.76750(14) 0.71731(13) 0.0127(3) Uani 1 1 d . . . . .
H9 H 0.332530 0.717111 0.766504 0.015 Uiso 1 1 calc R . . . .
C10 C 0.45512(16) 0.86860(14) 0.73903(13) 0.0126(3) Uani 1 1 d . . . . .
C11 C 0.39048(17) 0.89724(15) 0.83314(14) 0.0162(3) Uani 1 1 d . . . . .
H11 H 0.312378 0.849309 0.881460 0.019 Uiso 1 1 calc R . . . .
C12 C 0.43924(19) 0.99260(16) 0.85481(15) 0.0214(4) Uani 1 1 d . . . . .
H12 H 0.395444 1.009914 0.918550 0.026 Uiso 1 1 calc R . . . .
C13 C 0.5541(2) 1.06575(15) 0.78343(16) 0.0231(4) Uani 1 1 d . . . . .
H13 H 0.587649 1.131597 0.799711 0.028 Uiso 1 1 calc R . . . .
C14 C 0.37151(17) 0.62367(14) 0.24198(14) 0.0146(3) Uani 1 1 d . . . . .
H14 H 0.388922 0.659972 0.295883 0.018 Uiso 1 1 calc R . . . .
C15 C 0.44532(18) 0.66549(15) 0.12901(14) 0.0186(3) Uani 1 1 d . . . . .
H15 H 0.511687 0.731279 0.105495 0.022 Uiso 1 1 calc R . . . .
C16 C 0.15002(15) 0.64384(13) 0.47773(13) 0.0111(3) Uani 1 1 d . . . . .
C17 C 0.18511(15) 0.66514(13) 0.57653(13) 0.0106(3) Uani 1 1 d . . . . .
C18 C 0.17897(16) 0.42403(14) 0.81445(13) 0.0118(3) Uani 1 1 d . . . . .
C19 C 0.10659(17) 0.25438(15) 1.01050(14) 0.0165(3) Uani 1 1 d . . . . .
C20 C 0.0700(3) 0.16477(18) 0.95769(18) 0.0387(5) Uani 1 1 d . . . . .
H20A H 0.008739 0.204246 0.893615 0.058 Uiso 1 1 calc GR . . . .
H20B H 0.022769 0.091551 1.020951 0.058 Uiso 1 1 calc GR . . . .
H20C H 0.154697 0.140482 0.924300 0.058 Uiso 1 1 calc GR . . . .
C21 C 0.1883(2) 0.19050(16) 1.11876(15) 0.0241(4) Uani 1 1 d . . . . .
H21A H 0.271409 0.155704 1.094695 0.036 Uiso 1 1 calc GR . . . .
H21B H 0.130945 0.124239 1.181721 0.036 Uiso 1 1 calc GR . . . .
H21C H 0.215482 0.250296 1.149761 0.036 Uiso 1 1 calc GR . . . .
C22 C -0.01874(19) 0.31531(19) 1.04243(17) 0.0293(4) Uani 1 1 d . . . . .
H22A H 0.011213 0.375474 1.071957 0.044 Uiso 1 1 calc GR . . . .
H22B H -0.080071 0.252571 1.105283 0.044 Uiso 1 1 calc GR . . . .
H22C H -0.068491 0.357334 0.970717 0.044 Uiso 1 1 calc GR . . . .
C23 C 0.58781(16) 0.81696(14) 0.55318(14) 0.0135(3) Uani 1 1 d . . . . .
H23 H 0.632457 0.799567 0.489785 0.016 Uiso 1 1 calc R . . . .
C24 C 0.63458(16) 0.91358(14) 0.57356(14) 0.0151(3) Uani 1 1 d . . . . .
H24 H 0.711634 0.962429 0.524273 0.018 Uiso 1 1 calc R . . . .
C25 C 0.57024(16) 0.94262(14) 0.66716(14) 0.0141(3) Uani 1 1 d . . . . .
C26 C 0.61757(18) 1.04234(15) 0.69077(15) 0.0197(3) Uani 1 1 d . . . . .
H26 H 0.693695 1.093117 0.641996 0.024 Uiso 1 1 calc R . . . .
C27 C 0.11927(16) 0.75638(14) 0.60185(13) 0.0135(3) Uani 1 1 d . . . . .
H27 H 0.138235 0.769381 0.670848 0.016 Uiso 1 1 calc R . . . .
C28 C 0.02445(16) 0.82925(14) 0.52462(14) 0.0141(3) Uani 1 1 d . . . . .
H28 H -0.022621 0.891550 0.541377 0.017 Uiso 1 1 calc R . . . .
C29 C -0.00053(16) 0.81019(14) 0.42364(14) 0.0132(3) Uani 1 1 d . . . . .
C30 C 0.05962(16) 0.71580(14) 0.39809(13) 0.0127(3) Uani 1 1 d . . . . .
H30 H 0.039487 0.701900 0.329843 0.015 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 C29 1.9016(15) . ?
O1 C6 1.2150(18) . ?
O2 C18 1.2091(19) . ?
O3 C18 1.3429(18) . ?
O3 C19 1.4752(18) . ?
N1 C5 1.4563(18) . ?
N1 C6 1.3578(19) . ?
N1 C16 1.4063(19) . ?
N2 H2 0.8097 . ?
N2 C7 1.4465(19) . ?
N2 C8 1.3963(19) . ?
N3 H3 0.8117 . ?
N3 C7 1.4579(18) . ?
N3 C18 1.3681(19) . ?
C1 H1 0.9500 . ?
C1 C2 1.380(3) . ?
C1 C15 1.383(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.385(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.395(2) . ?
C4 C5 1.508(2) . ?
C4 C14 1.382(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.565(2) . ?
C7 C17 1.522(2) . ?
C8 C9 1.378(2) . ?
C8 C23 1.423(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.419(2) . ?
C10 C11 1.423(2) . ?
C10 C25 1.417(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.363(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.410(3) . ?
C13 H13 0.9500 . ?
C13 C26 1.369(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.400(2) . ?
C16 C30 1.379(2) . ?
C17 C27 1.383(2) . ?
C19 C20 1.513(2) . ?
C19 C21 1.518(2) . ?
C19 C22 1.514(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23 0.9500 . ?
C23 C24 1.361(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.419(2) . ?
C25 C26 1.419(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C27 C28 1.398(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.383(2) . ?
C29 C30 1.394(2) . ?
C30 H30 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
C18 O3 C19 121.99(12) . . ?
C6 N1 C5 122.91(12) . . ?
C6 N1 C16 111.37(12) . . ?
C16 N1 C5 125.19(13) . . ?
C7 N2 H2 116.3 . . ?
C8 N2 H2 116.4 . . ?
C8 N2 C7 125.25(12) . . ?
C7 N3 H3 113.9 . . ?
C18 N3 H3 115.7 . . ?
C18 N3 C7 120.25(12) . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C15 119.74(15) . . ?
C15 C1 H1 120.1 . . ?
C1 C2 H2A 119.8 . . ?
C1 C2 C3 120.31(15) . . ?
C3 C2 H2A 119.8 . . ?
C2 C3 H3A 119.9 . . ?
C2 C3 C4 120.25(16) . . ?
C4 C3 H3A 119.9 . . ?
C3 C4 C5 117.61(14) . . ?
C14 C4 C3 119.27(14) . . ?
C14 C4 C5 123.11(13) . . ?
N1 C5 C4 114.43(12) . . ?
N1 C5 H5A 108.7 . . ?
N1 C5 H5B 108.7 . . ?
C4 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
O1 C6 N1 126.77(13) . . ?
O1 C6 C7 125.13(13) . . ?
N1 C6 C7 108.08(12) . . ?
N2 C7 N3 108.56(12) . . ?
N2 C7 C6 105.32(11) . . ?
N2 C7 C17 112.77(12) . . ?
N3 C7 C6 111.77(12) . . ?
N3 C7 C17 116.46(12) . . ?
C17 C7 C6 101.28(11) . . ?
N2 C8 C23 116.50(13) . . ?
C9 C8 N2 124.27(14) . . ?
C9 C8 C23 119.19(14) . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.67(14) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 121.73(14) . . ?
C25 C10 C9 119.80(14) . . ?
C25 C10 C11 118.47(14) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.82(16) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.56(16) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.8 . . ?
C26 C13 C12 120.31(16) . . ?
C26 C13 H13 119.8 . . ?
C4 C14 H14 119.9 . . ?
C4 C14 C15 120.22(15) . . ?
C15 C14 H14 119.9 . . ?
C1 C15 C14 120.21(16) . . ?
C1 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 N1 110.25(13) . . ?
C30 C16 N1 126.69(14) . . ?
C30 C16 C17 123.06(14) . . ?
C16 C17 C7 107.96(12) . . ?
C27 C17 C7 132.74(13) . . ?
C27 C17 C16 119.21(14) . . ?
O2 C18 O3 127.29(14) . . ?
O2 C18 N3 124.02(14) . . ?
O3 C18 N3 108.68(13) . . ?
O3 C19 C20 111.06(13) . . ?
O3 C19 C21 102.13(13) . . ?
O3 C19 C22 109.00(13) . . ?
C20 C19 C21 110.16(15) . . ?
C20 C19 C22 112.88(17) . . ?
C22 C19 C21 111.10(14) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C8 C23 H23 119.5 . . ?
C24 C23 C8 120.91(14) . . ?
C24 C23 H23 119.5 . . ?
C23 C24 H24 119.4 . . ?
C23 C24 C25 121.15(14) . . ?
C25 C24 H24 119.4 . . ?
C10 C25 C24 118.28(14) . . ?
C10 C25 C26 119.47(15) . . ?
C24 C25 C26 122.24(15) . . ?
C13 C26 C25 120.36(16) . . ?
C13 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C17 C27 H27 120.4 . . ?
C17 C27 C28 119.14(14) . . ?
C28 C27 H27 120.4 . . ?
C27 C28 H28 120.2 . . ?
C29 C28 C27 119.68(14) . . ?
C29 C28 H28 120.2 . . ?
C28 C29 Br1 118.78(12) . . ?
C28 C29 C30 122.66(14) . . ?
C30 C29 Br1 118.55(11) . . ?
C16 C30 C29 116.04(14) . . ?
C16 C30 H30 122.0 . . ?
C29 C30 H30 122.0 . . ?

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 C29 C30 C16 178.70(11) . . . . ?
O1 C6 C7 N2 69.44(18) . . . . ?
O1 C6 C7 N3 -48.25(19) . . . . ?
O1 C6 C7 C17 -172.92(14) . . . . ?
N1 C6 C7 N2 -108.96(13) . . . . ?
N1 C6 C7 N3 133.34(13) . . . . ?
N1 C6 C7 C17 8.67(14) . . . . ?
N1 C16 C17 C7 8.52(16) . . . . ?
N1 C16 C17 C27 -174.48(13) . . . . ?
N1 C16 C30 C29 177.06(14) . . . . ?
N2 C7 C17 C16 101.93(14) . . . . ?
N2 C7 C17 C27 -74.5(2) . . . . ?
N2 C8 C9 C10 178.48(14) . . . . ?
N2 C8 C23 C24 -177.98(14) . . . . ?
N3 C7 C17 C16 -131.59(13) . . . . ?
N3 C7 C17 C27 52.0(2) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C1 C15 C14 1.1(2) . . . . ?
C2 C3 C4 C5 -179.08(15) . . . . ?
C2 C3 C4 C14 0.3(2) . . . . ?
C3 C4 C5 N1 -179.20(14) . . . . ?
C3 C4 C14 C15 0.5(2) . . . . ?
C4 C14 C15 C1 -1.2(2) . . . . ?
C5 N1 C6 O1 5.4(2) . . . . ?
C5 N1 C6 C7 -176.27(12) . . . . ?
C5 N1 C16 C17 169.17(13) . . . . ?
C5 N1 C16 C30 -10.3(2) . . . . ?
C5 C4 C14 C15 179.86(14) . . . . ?
C6 N1 C5 C4 -98.93(16) . . . . ?
C6 N1 C16 C17 -2.69(17) . . . . ?
C6 N1 C16 C30 177.86(14) . . . . ?
C6 C7 C17 C16 -10.14(14) . . . . ?
C6 C7 C17 C27 173.42(16) . . . . ?
C7 N2 C8 C9 23.2(2) . . . . ?
C7 N2 C8 C23 -158.88(14) . . . . ?
C7 N3 C18 O2 -17.3(2) . . . . ?
C7 N3 C18 O3 163.68(12) . . . . ?
C7 C17 C27 C28 172.88(15) . . . . ?
C8 N2 C7 N3 -70.22(17) . . . . ?
C8 N2 C7 C6 169.94(13) . . . . ?
C8 N2 C7 C17 60.37(18) . . . . ?
C8 C9 C10 C11 179.96(14) . . . . ?
C8 C9 C10 C25 -1.1(2) . . . . ?
C8 C23 C24 C25 -0.2(2) . . . . ?
C9 C8 C23 C24 0.0(2) . . . . ?
C9 C10 C11 C12 178.05(15) . . . . ?
C9 C10 C25 C24 0.9(2) . . . . ?
C9 C10 C25 C26 -178.93(14) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C10 C25 C26 C13 1.1(2) . . . . ?
C11 C10 C25 C24 179.87(14) . . . . ?
C11 C10 C25 C26 0.0(2) . . . . ?
C11 C12 C13 C26 0.5(3) . . . . ?
C12 C13 C26 C25 -1.3(3) . . . . ?
C14 C4 C5 N1 1.4(2) . . . . ?
C15 C1 C2 C3 -0.2(3) . . . . ?
C16 N1 C5 C4 90.10(17) . . . . ?
C16 N1 C6 O1 177.44(14) . . . . ?
C16 N1 C6 C7 -4.19(16) . . . . ?
C16 C17 C27 C28 -3.2(2) . . . . ?
C17 C16 C30 C29 -2.3(2) . . . . ?
C17 C27 C28 C29 -0.9(2) . . . . ?
C18 O3 C19 C20 57.4(2) . . . . ?
C18 O3 C19 C21 174.80(13) . . . . ?
C18 O3 C19 C22 -67.59(18) . . . . ?
C18 N3 C7 N2 -167.45(13) . . . . ?
C18 N3 C7 C6 -51.72(18) . . . . ?
C18 N3 C7 C17 64.00(18) . . . . ?
C19 O3 C18 O2 -3.8(2) . . . . ?
C19 O3 C18 N3 175.20(12) . . . . ?
C23 C8 C9 C10 0.6(2) . . . . ?
C23 C24 C25 C10 -0.3(2) . . . . ?
C23 C24 C25 C26 179.57(15) . . . . ?
C24 C25 C26 C13 -178.76(15) . . . . ?
C25 C10 C11 C12 -0.9(2) . . . . ?
C27 C28 C29 Br1 -177.08(11) . . . . ?
C27 C28 C29 C30 3.7(2) . . . . ?
C28 C29 C30 C16 -2.0(2) . . . . ?
C30 C16 C17 C7 -172.01(13) . . . . ?
C30 C16 C17 C27 5.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
