# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2024

####################################################################### 
# 
# 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_pn59_thfcyhx_a
_database_code_depnum_ccdc_archive 'CCDC 2327783'
loop_
_audit_author_name
_audit_author_address
'Phattananawee Nalaoh '
;University of Tennessee, Knoxville
United States of America
;
_audit_update_record             
;
2024-01-23 deposited with the CCDC.	2024-04-22 downloaded from the CCDC.
;
_audit_creation_date             2023-10-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 Br N O2'
_chemical_formula_sum            'C18 H16 Br N O2'
_chemical_formula_weight         358.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   17.6763(5)
_cell_length_b                   11.7042(3)
_cell_length_c                   7.5524(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.8400(10)
_cell_angle_gamma                90
_cell_volume                     1556.92(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9320
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.95
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.763
_shelx_estimated_absorpt_T_min   0.609
_exptl_absorpt_coefficient_mu    2.647
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0815 before and 0.0642 after correction.
The Ratio of minimum to maximum transmission is 0.8514.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.108
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            32763
_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         26.732
_diffrn_reflns_theta_min         2.313
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3135
_reflns_number_total             3304
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.626
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0339P)²+2.6046P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0817
_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. Uiso/Uaniso restraints and constraints
Uanis(C10) = Uanis(C9)
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C)
;
_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 0.25253(2) 0.45397(2) 0.96078(3) 0.01981(9) Uani 1 1 d . . . . .
O1 O 0.30988(9) 0.64470(13) 0.6730(2) 0.0186(3) Uani 1 1 d . . . . .
O2 O 0.41965(10) 0.67412(15) 0.8396(2) 0.0241(4) Uani 1 1 d . . . . .
N1 N 0.46561(12) 0.34226(18) 0.6490(3) 0.0238(4) Uani 1 1 d . . . . .
H1 H 0.504773 0.296567 0.641999 0.029 Uiso 1 1 calc R U . . .
C1 C 0.13264(13) 0.40870(19) 0.6906(3) 0.0177(4) Uani 1 1 d . . . . .
C2 C 0.10382(14) 0.37485(19) 0.5170(3) 0.0192(5) Uani 1 1 d . . . . .
C3 C 0.02423(14) 0.3565(2) 0.4820(4) 0.0243(5) Uani 1 1 d . . . . .
H3 H 0.004478 0.333332 0.366648 0.029 Uiso 1 1 calc R U . . .
C4 C -0.02375(14) 0.3716(2) 0.6115(4) 0.0270(6) Uani 1 1 d . . . . .
H4 H -0.076605 0.358300 0.586694 0.032 Uiso 1 1 calc R U . . .
C5 C 0.00475(15) 0.4069(2) 0.7821(4) 0.0259(5) Uani 1 1 d . . . . .
H5 H -0.029221 0.418143 0.871545 0.031 Uiso 1 1 calc R U . . .
C6 C 0.08076(14) 0.4252(2) 0.8211(3) 0.0218(5) Uani 1 1 d . . . . .
H6 H 0.098932 0.449231 0.937129 0.026 Uiso 1 1 calc R U . . .
C7 C 0.21307(13) 0.42030(19) 0.7233(3) 0.0167(4) Uani 1 1 d . . . . .
C8 C 0.26272(13) 0.40220(19) 0.5960(3) 0.0167(4) Uani 1 1 d . . . . .
C9 C 0.23156(14) 0.37075(19) 0.4161(3) 0.0204(3) Uani 1 1 d . . . . .
H9 H 0.264160 0.359516 0.323869 0.025 Uiso 1 1 calc R U . . .
C10 C 0.15493(13) 0.35797(19) 0.3840(3) 0.0204(3) Uani 1 1 d . . . . .
H10 H 0.134917 0.336901 0.267943 0.025 Uiso 1 1 calc R U . . .
C11 C 0.34634(13) 0.4046(2) 0.6295(3) 0.0176(4) Uani 1 1 d . . . . .
C12 C 0.39175(14) 0.3130(2) 0.6000(3) 0.0223(5) Uani 1 1 d . . . . .
H12 H 0.374884 0.241173 0.553291 0.027 Uiso 1 1 calc R U . . .
C13 C 0.47010(14) 0.4511(2) 0.7099(3) 0.0205(5) Uani 1 1 d . . . . .
C14 C 0.39653(13) 0.4942(2) 0.6995(3) 0.0178(4) Uani 1 1 d . . . . .
C15 C 0.54493(13) 0.5046(2) 0.7677(3) 0.0245(5) Uani 1 1 d . . . . .
H15A H 0.546471 0.582390 0.720238 0.037 Uiso 1 1 calc R U . . .
H15B H 0.585854 0.459212 0.723014 0.037 Uiso 1 1 calc R U . . .
H15C H 0.551517 0.507170 0.897794 0.037 Uiso 1 1 calc R U . . .
C16 C 0.37837(13) 0.6113(2) 0.7458(3) 0.0176(4) Uani 1 1 d . . . . .
C17 C 0.28585(14) 0.7587(2) 0.7210(3) 0.0206(5) Uani 1 1 d . . . . .
H17A H 0.312767 0.817253 0.655519 0.025 Uiso 1 1 calc R U . . .
H17B H 0.297163 0.771786 0.849992 0.025 Uiso 1 1 calc R U . . .
C18 C 0.20125(14) 0.7655(2) 0.6717(3) 0.0249(5) Uani 1 1 d . . . . .
H18A H 0.182278 0.840012 0.707121 0.037 Uiso 1 1 calc R U . . .
H18B H 0.175573 0.704786 0.732984 0.037 Uiso 1 1 calc R U . . .
H18C H 0.191065 0.756007 0.542927 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.910(2) . ?
O1 C16 1.345(3) . ?
O1 C17 1.455(3) . ?
O2 C16 1.220(3) . ?
N1 H1 0.8800 . ?
N1 C12 1.370(3) . ?
N1 C13 1.355(3) . ?
C1 C2 1.422(3) . ?
C1 C6 1.415(3) . ?
C1 C7 1.429(3) . ?
C2 C3 1.426(3) . ?
C2 C10 1.420(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.359(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.405(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.368(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.372(3) . ?
C8 C9 1.469(3) . ?
C8 C11 1.479(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.364(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.368(3) . ?
C11 C14 1.445(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 C15 1.495(3) . ?
C14 C16 1.456(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.512(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C16 O1 C17 115.89(18) . . ?
C12 N1 H1 124.6 . . ?
C13 N1 H1 124.6 . . ?
C13 N1 C12 110.7(2) . . ?
C2 C1 C7 117.4(2) . . ?
C6 C1 C2 118.5(2) . . ?
C6 C1 C7 124.1(2) . . ?
C1 C2 C3 119.0(2) . . ?
C10 C2 C1 119.4(2) . . ?
C10 C2 C3 121.6(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.1(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 H6 119.6 . . ?
C1 C7 Br1 117.47(17) . . ?
C8 C7 Br1 119.04(17) . . ?
C8 C7 C1 123.4(2) . . ?
C7 C8 C9 118.3(2) . . ?
C7 C8 C11 124.5(2) . . ?
C9 C8 C11 117.0(2) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.7(2) . . ?
C10 C9 H9 120.6 . . ?
C2 C10 H10 118.6 . . ?
C9 C10 C2 122.7(2) . . ?
C9 C10 H10 118.6 . . ?
C12 C11 C8 123.3(2) . . ?
C12 C11 C14 106.1(2) . . ?
C14 C11 C8 130.5(2) . . ?
N1 C12 H12 125.7 . . ?
C11 C12 N1 108.6(2) . . ?
C11 C12 H12 125.7 . . ?
N1 C13 C14 107.1(2) . . ?
N1 C13 C15 121.2(2) . . ?
C14 C13 C15 131.7(2) . . ?
C11 C14 C16 129.0(2) . . ?
C13 C14 C11 107.4(2) . . ?
C13 C14 C16 123.5(2) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C16 C14 112.62(19) . . ?
O2 C16 O1 122.4(2) . . ?
O2 C16 C14 125.0(2) . . ?
O1 C17 H17A 110.3 . . ?
O1 C17 H17B 110.3 . . ?
O1 C17 C18 106.9(2) . . ?
H17A C17 H17B 108.6 . . ?
C18 C17 H17A 110.3 . . ?
C18 C17 H17B 110.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 C7 C8 C9 176.98(16) . . . . ?
Br1 C7 C8 C11 1.3(3) . . . . ?
N1 C13 C14 C11 0.4(3) . . . . ?
N1 C13 C14 C16 -177.1(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C1 C2 C10 C9 1.3(3) . . . . ?
C1 C7 C8 C9 0.8(3) . . . . ?
C1 C7 C8 C11 -174.9(2) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
C2 C1 C7 Br1 -175.18(16) . . . . ?
C2 C1 C7 C8 1.0(3) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C2 C10 C9 -177.4(2) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C6 C1 C2 C3 -1.3(3) . . . . ?
C6 C1 C2 C10 179.9(2) . . . . ?
C6 C1 C7 Br1 2.7(3) . . . . ?
C6 C1 C7 C8 178.9(2) . . . . ?
C7 C1 C2 C3 176.7(2) . . . . ?
C7 C1 C2 C10 -2.1(3) . . . . ?
C7 C1 C6 C5 -176.6(2) . . . . ?
C7 C8 C9 C10 -1.7(3) . . . . ?
C7 C8 C11 C12 119.8(3) . . . . ?
C7 C8 C11 C14 -58.5(4) . . . . ?
C8 C9 C10 C2 0.6(3) . . . . ?
C8 C11 C12 N1 -178.3(2) . . . . ?
C8 C11 C14 C13 178.0(2) . . . . ?
C8 C11 C14 C16 -4.6(4) . . . . ?
C9 C8 C11 C12 -55.9(3) . . . . ?
C9 C8 C11 C14 125.8(3) . . . . ?
C10 C2 C3 C4 179.1(2) . . . . ?
C11 C8 C9 C10 174.4(2) . . . . ?
C11 C14 C16 O1 -17.4(3) . . . . ?
C11 C14 C16 O2 162.8(2) . . . . ?
C12 N1 C13 C14 -0.2(3) . . . . ?
C12 N1 C13 C15 -178.5(2) . . . . ?
C12 C11 C14 C13 -0.5(3) . . . . ?
C12 C11 C14 C16 176.9(2) . . . . ?
C13 N1 C12 C11 -0.2(3) . . . . ?
C13 C14 C16 O1 159.6(2) . . . . ?
C13 C14 C16 O2 -20.3(4) . . . . ?
C14 C11 C12 N1 0.4(3) . . . . ?
C15 C13 C14 C11 178.5(2) . . . . ?
C15 C13 C14 C16 1.0(4) . . . . ?
C16 O1 C17 C18 -163.74(19) . . . . ?
C17 O1 C16 O2 -3.4(3) . . . . ?
C17 O1 C16 C14 176.80(18) . . . . ?

_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_pn60_a
_database_code_depnum_ccdc_archive 'CCDC 2327784'
loop_
_audit_author_name
_audit_author_address
'Phattananawee Nalaoh'
;University of Tennessee, Knoxville
United States of America
;
_audit_update_record             
;
2024-01-23 deposited with the CCDC.	2024-04-22 downloaded from the CCDC.
;
_audit_creation_date             2023-10-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 Br N2 O4'
_chemical_formula_sum            'C19 H17 Br N2 O4'
_chemical_formula_weight         417.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.445(3)
_cell_length_b                   12.529(3)
_cell_length_c                   11.461(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.804(5)
_cell_angle_gamma                90
_cell_volume                     1783.1(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.861
_shelx_estimated_absorpt_T_min   0.334
_exptl_absorpt_coefficient_mu    2.333
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1573 before and 0.0731 after correction.
The Ratio of minimum to maximum transmission is 0.7961.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 -1.00 -1.00 0.1960
0.00 0.00 -1.00 0.2980
-1.00 -1.00 0.00 0.0210
1.00 1.00 0.00 0.0330
1.00 -1.00 0.00 0.0220
-1.00 1.00 0.00 0.0510
0.00 0.00 1.00 0.2950

_exptl_crystal_size_max          0.602
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.066
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            29690
_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         26.386
_diffrn_reflns_theta_min         2.309
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3237
_reflns_number_total             3650
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.244
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3650
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.046
_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)+(0.0388P)²+2.8303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0909
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O3-N3 \\sim O3A-N3
 with sigma of 0.02
 O5-N3 \\sim O5A-N3
 with sigma of 0.02
 Br1-C7 \\sim Br1-C7A
 with sigma of 0.02
 C1-C2 \\sim C1A-C2A
 with sigma of 0.02
 C1-C6 \\sim C1A-C6A
 with sigma of 0.02
 C1-C7 \\sim C1A-C7A
 with sigma of 0.02
 C2-C3 \\sim C2A-C3A
 with sigma of 0.02
 C2-C10 \\sim C2A-C10A
 with sigma of 0.02
 C3-C4 \\sim C3A-C4A
 with sigma of 0.02
 C4-C5 \\sim C4A-C5A
 with sigma of 0.02
 C5-C6 \\sim C5A-C6A
 with sigma of 0.02
 C7-C8 \\sim C7A-C8
 with sigma of 0.02
 C8-C9 \\sim C8-C9A
 with sigma of 0.02
 C9-C10 \\sim C9A-C10A
 with sigma of 0.02
 Br1-C1 \\sim Br1-C1A
 with sigma of 0.04
 C1-C3 \\sim C1A-C3A
 with sigma of 0.04
 C1-C5 \\sim C1A-C5A
 with sigma of 0.04
 C1-C8 \\sim C1A-C8
 with sigma of 0.04
 C1-C10 \\sim C1A-C10A
 with sigma of 0.04
 C2-C4 \\sim C2A-C4A
 with sigma of 0.04
 C2-C6 \\sim C2A-C6A
 with sigma of 0.04
 C2-C7 \\sim C2A-C7A
 with sigma of 0.04
 C2-C9 \\sim C2A-C9A
 with sigma of 0.04
 C3-C5 \\sim C3A-C5A
 with sigma of 0.04
 C3-C10 \\sim C3A-C10A
 with sigma of 0.04
 C4-C6 \\sim C4A-C6A
 with sigma of 0.04
 C6-C7 \\sim C6A-C7A
 with sigma of 0.04
 C8-C10 \\sim C8-C10A
 with sigma of 0.04
 C7-C8 \\sim C7-C8A
 with sigma of 0.02
 C8-C9 \\sim C8A-C9
 with sigma of 0.02
 C8-C11 \\sim C8A-C11
 with sigma of 0.02
 C8-C9A \\sim C8A-C9A
 with sigma of 0.02
 C8-C7A \\sim C8A-C7A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C11) = Uanis(C9)
Uanis(C1A) = Uanis(C10A)
Uanis(C12) = Uanis(C1A)
Uanis(C18) = Uanis(C10)
Uanis(C2A) = Uanis(C3A)
Uanis(C4A) = Uanis(C7A)
Uanis(C16) = Uanis(C6)
Uanis(C8) = Uanis(C8A)
Uanis(C12) = Uanis(C8)
Uanis(C4A) = Uanis(C5)
Uanis(C13) = Uanis(C9A)
Uanis(C14) = Uanis(C7)
Uanis(O5) = Uanis(O3A)
Uanis(C10A) = Uanis(C9A)
4. Others
 Fixed Sof: O3(0.5) O5(0.5) C1(0.5) C2(0.5) C3(0.5) H3(0.5) C4(0.5) H4(0.5)
 C5(0.5) H5(0.5) C6(0.5) H6(0.5) C7(0.5) C8(0.5) C9(0.5) H9(0.5) C10(0.5)
 H10(0.5) O5A(0.5) O3A(0.5) C6A(0.5) H6A(0.5) C5A(0.5) H5A(0.5) C4A(0.5)
 H4A(0.5) C3A(0.5) H3A(0.5) C2A(0.5) C10A(0.5) H10A(0.5) C9A(0.5) H9A(0.5)
 C1A(0.5) C7A(0.5) C8A(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B), C19(H19A,H19B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C14(H14), C6A(H6A),
 C5A(H5A), C4A(H4A), C3A(H3A), C10A(H10A), C9A(H9A)
5.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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 0.56978(2) 0.90395(2) 0.93320(2) 0.02934(10) Uani 1 1 d D . . . .
O2 O 0.25202(14) 0.58917(14) 0.67927(16) 0.0250(4) Uani 1 1 d . . . . .
O3 O 0.1435(7) 0.6283(6) 0.2585(5) 0.0314(14) Uani 0.5 1 d D . P A 1
O4 O 0.37084(14) 0.57694(13) 0.83510(15) 0.0216(4) Uani 1 1 d . . . . .
O5 O 0.0929(9) 0.7610(10) 0.3531(12) 0.050(2) Uani 0.5 1 d D . P A 1
N2 N 0.42871(17) 0.84169(17) 0.56999(18) 0.0224(4) Uani 1 1 d . . . . .
H2 H 0.421756 0.889313 0.513554 0.027 Uiso 1 1 calc R U . . .
N3 N 0.15695(19) 0.6860(2) 0.3390(2) 0.0332(6) Uani 1 1 d D . . . .
C1 C 0.7277(13) 0.7284(11) 0.9672(16) 0.032(2) Uani 0.5 1 d D . P B 1
C2 C 0.7681(16) 0.6287(12) 0.932(2) 0.024(2) Uani 0.5 1 d D . P B 1
C3 C 0.8655(11) 0.5913(10) 0.9866(12) 0.027(2) Uani 0.5 1 d D . P B 1
H3 H 0.893528 0.524752 0.963208 0.032 Uiso 0.5 1 calc R U P B 1
C4 C 0.9199(7) 0.6477(6) 1.0714(7) 0.0261(18) Uani 0.5 1 d D . P B 1
H4 H 0.985515 0.620573 1.106703 0.031 Uiso 0.5 1 calc R U P B 1
C5 C 0.8799(7) 0.7466(7) 1.1080(8) 0.0217(11) Uani 0.5 1 d D . P B 1
H5 H 0.920440 0.786049 1.166428 0.026 Uiso 0.5 1 calc R U P B 1
C6 C 0.7824(10) 0.7883(11) 1.0606(13) 0.0303(6) Uani 0.5 1 d D . P B 1
H6 H 0.753594 0.852874 1.088646 0.036 Uiso 0.5 1 calc R U P B 1
C7 C 0.6349(11) 0.7696(9) 0.9012(14) 0.0208(5) Uani 0.5 1 d D . P B 1
C8 C 0.5838(12) 0.7048(10) 0.8060(12) 0.0195(3) Uani 0.5 1 d D . P B 2
C9 C 0.6206(4) 0.6116(4) 0.7961(5) 0.0169(4) Uani 0.5 1 d D . P B 1
H9 H 0.578556 0.569521 0.741367 0.020 Uiso 0.5 1 calc R U P B 1
C10 C 0.7070(6) 0.5618(6) 0.8463(7) 0.0244(5) Uani 0.5 1 d D . P B 1
H10 H 0.726549 0.490725 0.828266 0.029 Uiso 0.5 1 calc R U P B 1
C11 C 0.49942(18) 0.75051(18) 0.7222(2) 0.0169(4) Uani 1 1 d D . . . .
C12 C 0.39515(19) 0.70718(19) 0.6876(2) 0.0195(3) Uani 1 1 d . . . . .
C13 C 0.35342(19) 0.76792(19) 0.5925(2) 0.0195(3) Uani 1 1 d . . . . .
C14 C 0.5171(2) 0.83223(19) 0.6469(2) 0.0208(5) Uani 1 1 d . . . . .
H14 H 0.580119 0.875143 0.647681 0.025 Uiso 1 1 calc R U . . .
C15 C 0.34107(19) 0.61941(19) 0.7425(2) 0.0182(5) Uani 1 1 d . . . . .
C16 C 0.1893(2) 0.5036(2) 0.7265(2) 0.0303(6) Uani 1 1 d . . . . .
H16A H 0.164537 0.523883 0.803771 0.036 Uiso 1 1 calc R U . . .
H16B H 0.232996 0.437703 0.735737 0.036 Uiso 1 1 calc R U . . .
C17 C 0.0945(2) 0.4861(3) 0.6399(3) 0.0383(7) Uani 1 1 d . . . . .
H17A H 0.120354 0.469581 0.563027 0.057 Uiso 1 1 calc R U . . .
H17B H 0.050332 0.550894 0.634403 0.057 Uiso 1 1 calc R U . . .
H17C H 0.051091 0.426453 0.665938 0.057 Uiso 1 1 calc R U . . .
C18 C 0.2488(2) 0.7653(2) 0.5198(2) 0.0244(5) Uani 1 1 d . . . . .
H18A H 0.235081 0.835829 0.482754 0.029 Uiso 1 1 calc R U . . .
H18B H 0.189127 0.749696 0.570220 0.029 Uiso 1 1 calc R U . . .
C19 C 0.2532(2) 0.6799(2) 0.4260(2) 0.0245(5) Uani 1 1 d . . . . .
H19A H 0.319903 0.688974 0.384416 0.029 Uiso 1 1 calc R U . . .
H19B H 0.255684 0.608630 0.463276 0.029 Uiso 1 1 calc R U . . .
O5A O 0.0996(11) 0.7595(8) 0.3257(11) 0.065(4) Uani 0.5 1 d D . P A 2
O3A O 0.1483(8) 0.5970(7) 0.2843(7) 0.050(2) Uani 0.5 1 d D . P A 2
C6A C 0.7708(10) 0.8038(9) 1.0567(12) 0.032(2) Uani 0.5 1 d D . P B 2
H6A H 0.738101 0.870211 1.072856 0.039 Uiso 0.5 1 calc R U P B 2
C5A C 0.8614(6) 0.7740(7) 1.1228(8) 0.0287(19) Uani 0.5 1 d D . P B 2
H5A H 0.888040 0.815909 1.187469 0.034 Uiso 0.5 1 calc R U P B 2
C4A C 0.9144(7) 0.6792(7) 1.0921(7) 0.0217(11) Uani 0.5 1 d D . P B 2
H4A H 0.982034 0.661433 1.130596 0.026 Uiso 0.5 1 calc R U P B 2
C3A C 0.8699(11) 0.6138(11) 1.0087(13) 0.028(2) Uani 0.5 1 d D . P B 2
H3A H 0.905339 0.549082 0.991662 0.033 Uiso 0.5 1 calc R U P B 2
C2A C 0.7709(18) 0.6400(16) 0.946(2) 0.028(2) Uani 0.5 1 d D . P B 2
C10A C 0.7213(5) 0.5754(6) 0.8588(6) 0.0195(3) Uani 0.5 1 d D . P B 2
H10A H 0.755385 0.508019 0.852415 0.023 Uiso 0.5 1 calc R U P B 2
C9A C 0.6329(5) 0.5884(4) 0.7794(5) 0.0195(3) Uani 0.5 1 d D . P B 2
H9A H 0.606617 0.539077 0.721334 0.023 Uiso 0.5 1 calc R U P B 2
C1A C 0.7230(13) 0.7390(12) 0.9644(16) 0.0195(3) Uani 0.5 1 d D . P B 2
C7A C 0.6271(10) 0.7674(10) 0.8942(13) 0.0217(11) Uani 0.5 1 d D . P B 2
C8A C 0.5827(12) 0.7132(10) 0.8107(12) 0.0195(3) Uani 0.5 1 d D . P B 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.914(9) . ?
Br1 C7A 1.918(10) . ?
O2 C15 1.338(3) . ?
O2 C16 1.452(3) . ?
O3 N3 1.175(7) . ?
O4 C15 1.223(3) . ?
O5 N3 1.250(9) . ?
N2 H2 0.8800 . ?
N2 C13 1.353(3) . ?
N2 C14 1.368(3) . ?
N3 C19 1.509(3) . ?
N3 O5A 1.169(9) . ?
N3 O3A 1.279(8) . ?
C1 C2 1.416(10) . ?
C1 C6 1.441(10) . ?
C1 C7 1.434(9) . ?
C2 C3 1.407(9) . ?
C2 C10 1.465(10) . ?
C3 H3 0.9500 . ?
C3 C4 1.346(10) . ?
C4 H4 0.9500 . ?
C4 C5 1.410(9) . ?
C5 H5 0.9500 . ?
C5 C6 1.398(11) . ?
C6 H6 0.9500 . ?
C7 C8A 1.380(15) . ?
C8 C11 1.490(10) . ?
C8 C9A 1.617(12) . ?
C8 C7A 1.362(15) . ?
C9 H9 0.9500 . ?
C9 C10 1.339(8) . ?
C9 C8A 1.371(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.438(3) . ?
C11 C14 1.367(3) . ?
C11 C8A 1.477(10) . ?
C12 C13 1.401(3) . ?
C12 C15 1.454(3) . ?
C13 C18 1.499(3) . ?
C14 H14 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.507(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.521(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C6A H6A 0.9500 . ?
C6A C5A 1.368(9) . ?
C6A C1A 1.430(9) . ?
C5A H5A 0.9500 . ?
C5A C4A 1.414(10) . ?
C4A H4A 0.9500 . ?
C4A C3A 1.350(10) . ?
C3A H3A 0.9500 . ?
C3A C2A 1.424(10) . ?
C2A C10A 1.396(10) . ?
C2A C1A 1.398(11) . ?
C10A H10A 0.9500 . ?
C10A C9A 1.391(7) . ?
C9A H9A 0.9500 . ?
C1A C7A 1.439(9) . ?

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 O2 C16 117.0(2) . . ?
C13 N2 H2 124.6 . . ?
C13 N2 C14 110.8(2) . . ?
C14 N2 H2 124.6 . . ?
O3 N3 O5 120.3(7) . . ?
O3 N3 C19 123.6(4) . . ?
O5 N3 C19 116.0(6) . . ?
O5A N3 C19 125.2(6) . . ?
O5A N3 O3A 126.3(7) . . ?
O3A N3 C19 108.5(4) . . ?
C2 C1 C6 120.8(8) . . ?
C2 C1 C7 117.1(9) . . ?
C7 C1 C6 122.0(9) . . ?
C1 C2 C10 121.2(9) . . ?
C3 C2 C1 118.6(7) . . ?
C3 C2 C10 120.1(7) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.6(7) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.3(7) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.8(8) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 H6 121.6 . . ?
C5 C6 C1 116.8(10) . . ?
C5 C6 H6 121.6 . . ?
C1 C7 Br1 123.4(8) . . ?
C8A C7 Br1 114.2(7) . . ?
C8A C7 C1 122.3(9) . . ?
C11 C8 C9A 118.9(7) . . ?
C7A C8 C11 119.0(8) . . ?
C7A C8 C9A 121.6(8) . . ?
C10 C9 H9 114.6 . . ?
C10 C9 C8A 130.7(6) . . ?
C8A C9 H9 114.6 . . ?
C2 C10 H10 123.6 . . ?
C9 C10 C2 112.8(7) . . ?
C9 C10 H10 123.6 . . ?
C12 C11 C8 128.1(7) . . ?
C12 C11 C8A 130.5(7) . . ?
C14 C11 C8 124.0(7) . . ?
C14 C11 C12 106.8(2) . . ?
C14 C11 C8A 122.4(7) . . ?
C11 C12 C15 126.9(2) . . ?
C13 C12 C11 106.9(2) . . ?
C13 C12 C15 126.1(2) . . ?
N2 C13 C12 107.1(2) . . ?
N2 C13 C18 119.7(2) . . ?
C12 C13 C18 133.2(2) . . ?
N2 C14 H14 125.8 . . ?
C11 C14 N2 108.4(2) . . ?
C11 C14 H14 125.8 . . ?
O2 C15 C12 111.7(2) . . ?
O4 C15 O2 122.6(2) . . ?
O4 C15 C12 125.6(2) . . ?
O2 C16 H16A 110.5 . . ?
O2 C16 H16B 110.5 . . ?
O2 C16 C17 106.2(2) . . ?
H16A C16 H16B 108.7 . . ?
C17 C16 H16A 110.5 . . ?
C17 C16 H16B 110.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C18 H18A 109.7 . . ?
C13 C18 H18B 109.7 . . ?
C13 C18 C19 109.7(2) . . ?
H18A C18 H18B 108.2 . . ?
C19 C18 H18A 109.7 . . ?
C19 C18 H18B 109.7 . . ?
N3 C19 C18 111.5(2) . . ?
N3 C19 H19A 109.3 . . ?
N3 C19 H19B 109.3 . . ?
C18 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C5A C6A H6A 118.6 . . ?
C5A C6A C1A 122.8(8) . . ?
C1A C6A H6A 118.6 . . ?
C6A C5A H5A 120.9 . . ?
C6A C5A C4A 118.2(7) . . ?
C4A C5A H5A 120.9 . . ?
C5A C4A H4A 119.7 . . ?
C3A C4A C5A 120.6(8) . . ?
C3A C4A H4A 119.7 . . ?
C4A C3A H3A 119.4 . . ?
C4A C3A C2A 121.3(9) . . ?
C2A C3A H3A 119.4 . . ?
C10A C2A C3A 123.7(10) . . ?
C10A C2A C1A 116.8(9) . . ?
C1A C2A C3A 119.3(9) . . ?
C2A C10A H10A 113.1 . . ?
C9A C10A C2A 133.9(8) . . ?
C9A C10A H10A 113.1 . . ?
C8 C9A H9A 127.0 . . ?
C10A C9A C8 105.9(6) . . ?
C10A C9A H9A 127.0 . . ?
C6A C1A C7A 124.2(8) . . ?
C2A C1A C6A 117.1(8) . . ?
C2A C1A C7A 118.7(8) . . ?
C8 C7A Br1 123.5(7) . . ?
C8 C7A C1A 123.0(9) . . ?
C1A C7A Br1 113.5(7) . . ?
C7 C8A C11 128.8(9) . . ?
C9 C8A C7 114.7(8) . . ?
C9 C8A C11 116.2(8) . . ?

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 C7 C8A C9 -172.5(11) . . . . ?
Br1 C7 C8A C11 14(3) . . . . ?
O3 N3 C19 C18 179.6(5) . . . . ?
O5 N3 C19 C18 3.4(9) . . . . ?
N2 C13 C18 C19 98.5(3) . . . . ?
C1 C2 C3 C4 0(3) . . . . ?
C1 C2 C10 C9 9(3) . . . . ?
C1 C7 C8A C9 6(3) . . . . ?
C1 C7 C8A C11 -168.4(18) . . . . ?
C2 C1 C6 C5 4(3) . . . . ?
C2 C1 C7 Br1 -178.9(19) . . . . ?
C2 C1 C7 C8A 3(3) . . . . ?
C2 C3 C4 C5 0.1(18) . . . . ?
C3 C2 C10 C9 -175.5(14) . . . . ?
C3 C4 C5 C6 1.7(17) . . . . ?
C4 C5 C6 C1 -4(2) . . . . ?
C6 C1 C2 C3 -3(3) . . . . ?
C6 C1 C2 C10 173(2) . . . . ?
C6 C1 C7 Br1 -3(3) . . . . ?
C6 C1 C7 C8A 179.3(19) . . . . ?
C7 C1 C2 C3 173.4(18) . . . . ?
C7 C1 C2 C10 -11(4) . . . . ?
C7 C1 C6 C5 -171.6(18) . . . . ?
C8 C11 C12 C13 -169.5(7) . . . . ?
C8 C11 C12 C15 12.3(8) . . . . ?
C8 C11 C14 N2 169.8(6) . . . . ?
C10 C2 C3 C4 -175(2) . . . . ?
C10 C9 C8A C7 -8(2) . . . . ?
C10 C9 C8A C11 166.4(9) . . . . ?
C11 C8 C9A C10A 169.6(11) . . . . ?
C11 C8 C7A Br1 11(2) . . . . ?
C11 C8 C7A C1A -166.9(18) . . . . ?
C11 C12 C13 N2 1.1(3) . . . . ?
C11 C12 C13 C18 -178.2(3) . . . . ?
C11 C12 C15 O2 -171.2(2) . . . . ?
C11 C12 C15 O4 9.0(4) . . . . ?
C12 C11 C14 N2 1.0(3) . . . . ?
C12 C11 C8A C7 -127.9(17) . . . . ?
C12 C11 C8A C9 58.2(16) . . . . ?
C12 C13 C18 C19 -82.3(3) . . . . ?
C13 N2 C14 C11 -0.3(3) . . . . ?
C13 C12 C15 O2 10.9(3) . . . . ?
C13 C12 C15 O4 -168.8(2) . . . . ?
C13 C18 C19 N3 -171.0(2) . . . . ?
C14 N2 C13 C12 -0.5(3) . . . . ?
C14 N2 C13 C18 178.9(2) . . . . ?
C14 C11 C12 C13 -1.3(3) . . . . ?
C14 C11 C12 C15 -179.4(2) . . . . ?
C14 C11 C8A C7 60(2) . . . . ?
C14 C11 C8A C9 -114.2(11) . . . . ?
C15 O2 C16 C17 179.6(2) . . . . ?
C15 C12 C13 N2 179.3(2) . . . . ?
C15 C12 C13 C18 0.0(4) . . . . ?
C16 O2 C15 O4 1.2(3) . . . . ?
C16 O2 C15 C12 -178.6(2) . . . . ?
O5A N3 C19 C18 17.5(9) . . . . ?
O3A N3 C19 C18 -161.5(5) . . . . ?
C6A C5A C4A C3A -7.5(16) . . . . ?
C6A C1A C7A Br1 2(3) . . . . ?
C6A C1A C7A C8 179(2) . . . . ?
C5A C6A C1A C2A 2(3) . . . . ?
C5A C6A C1A C7A 179.3(19) . . . . ?
C5A C4A C3A C2A 3(2) . . . . ?
C4A C3A C2A C10A 180(3) . . . . ?
C4A C3A C2A C1A 5(3) . . . . ?
C3A C2A C10A C9A -172.5(14) . . . . ?
C3A C2A C1A C6A -7(4) . . . . ?
C3A C2A C1A C7A 176(2) . . . . ?
C2A C10A C9A C8 -2(3) . . . . ?
C2A C1A C7A Br1 179(2) . . . . ?
C2A C1A C7A C8 -4(4) . . . . ?
C10A C2A C1A C6A 177(2) . . . . ?
C10A C2A C1A C7A 0(4) . . . . ?
C9A C8 C11 C12 59.8(15) . . . . ?
C9A C8 C11 C14 -106.5(11) . . . . ?
C9A C8 C7A Br1 -177.9(11) . . . . ?
C9A C8 C7A C1A 4(3) . . . . ?
C1A C6A C5A C4A 5(2) . . . . ?
C1A C2A C10A C9A 3(4) . . . . ?
C7A C8 C11 C12 -128.5(14) . . . . ?
C7A C8 C11 C14 65.1(18) . . . . ?
C7A C8 C9A C10A -1.8(19) . . . . ?
C8A C9 C10 C2 1(2) . . . . ?
C8A C11 C12 C13 -174.6(7) . . . . ?
C8A C11 C12 C15 7.3(8) . . . . ?
C8A C11 C14 N2 174.9(6) . . . . ?

_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_ncsu_pn66_chcl3cyhx_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2327785'
loop_
_audit_author_name
_audit_author_address
'Phattananawee Nalaoh'
;University of Tennessee, Knoxville
United States of America
;
_audit_update_record             
;
2024-01-23 deposited with the CCDC.	2024-04-22 downloaded from the CCDC.
;
_audit_creation_date             2023-12-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H29 Br N2 O4'
_chemical_formula_sum            'C27 H29 Br N2 O4'
_chemical_formula_weight         525.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.7636(4)
_cell_length_b                   11.7049(3)
_cell_length_c                   15.5223(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.0750(10)
_cell_angle_gamma                90
_cell_volume                     2467.74(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9449
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      27.121
_cell_measurement_theta_min      2.373
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.702
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1440 before and 0.0741 after correction.
The Ratio of minimum to maximum transmission is 0.7038.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.723
_exptl_crystal_size_mid          0.575
_exptl_crystal_size_min          0.334
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            37538
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.128
_diffrn_reflns_theta_min         2.297
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5020
_reflns_number_total             5441
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5441
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.191
_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)+(0.0084P)²+2.6272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0820
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Br1-C8 \\sim Br1A-C8A
 with sigma of 0.02
 C1-C3 \\sim C1A-C3A
 with sigma of 0.02
 C1-C10 \\sim C1A-C10A
 with sigma of 0.02
 C2-C3 \\sim C2A-C3A
 with sigma of 0.02
 C2-C7 \\sim C2A-C7A
 with sigma of 0.02
 C2-C8 \\sim C2A-C8A
 with sigma of 0.02
 C3-C4 \\sim C3A-C4A
 with sigma of 0.02
 C4-C5 \\sim C4A-C5A
 with sigma of 0.02
 C5-C6 \\sim C5A-C6A
 with sigma of 0.02
 C6-C7 \\sim C6A-C7A
 with sigma of 0.02
 C8-C9 \\sim C8A-C9A
 with sigma of 0.02
 C9-C10 \\sim C9A-C10A
 with sigma of 0.02
 C9-C11 \\sim C9A-C11
 with sigma of 0.02
 Br1-C2 \\sim Br1A-C2A
 with sigma of 0.04
 Br1-C9 \\sim Br1A-C9A
 with sigma of 0.04
 C1-C2 \\sim C1A-C2A
 with sigma of 0.04
 C1-C4 \\sim C1A-C4A
 with sigma of 0.04
 C1-C9 \\sim C1A-C9A
 with sigma of 0.04
 C2-C4 \\sim C2A-C4A
 with sigma of 0.04
 C2-C6 \\sim C2A-C6A
 with sigma of 0.04
 C2-C9 \\sim C2A-C9A
 with sigma of 0.04
 C3-C5 \\sim C3A-C5A
 with sigma of 0.04
 C3-C7 \\sim C3A-C7A
 with sigma of 0.04
 C3-C8 \\sim C3A-C8A
 with sigma of 0.04
 C3-C10 \\sim C3A-C10A
 with sigma of 0.04
 C4-C6 \\sim C4A-C6A
 with sigma of 0.04
 C5-C7 \\sim C5A-C7A
 with sigma of 0.04
 C7-C8 \\sim C7A-C8A
 with sigma of 0.04
 C8-C10 \\sim C8A-C10A
 with sigma of 0.04
 C8-C11 \\sim C8A-C11
 with sigma of 0.04
 C10-C11 \\sim C10A-C11
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C2A) = Uanis(C3A)
Uanis(C5) = Uanis(C5A)
Uanis(C6) = Uanis(C4A)
Uanis(C7) = Uanis(C10)
Uanis(C9A) = Uanis(C2A)
Uanis(C1) = Uanis(C10A)
Uanis(C5) = Uanis(C6A)
4. Others
 Sof(C10A)=Sof(H10A)=Sof(C7A)=Sof(H7A)=Sof(C5A)=Sof(H5A)=Sof(C3A)=Sof(C8A)=
 Sof(C2A)=Sof(C6A)=Sof(H6A)=Sof(C9A)=Sof(C4A)=Sof(H4A)=Sof(C1A)=Sof(H1AA)=
 Sof(Br1A)=1-FVAR(1)
 Sof(Br1)=Sof(C1)=Sof(H1A)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=
 Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(C9)=Sof(C10)=Sof(H10)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C25(H25)
5.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C21(H21A,H21B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C14(H14), C18(H18),
 C10A(H10A), C7A(H7A), C5A(H5A), C6A(H6A), C4A(H4A), C1A(H1AA)
5.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C)
;
_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 0.61053(2) 0.78272(2) 0.25512(2) 0.02078(8) Uani 0.8353(10) 1 d D . P A
1
O2 O 0.63326(10) 0.49454(13) 0.28790(9) 0.0203(3) Uani 1 1 d . . . . .
O3 O 0.79001(10) 0.46860(13) 0.38878(10) 0.0225(3) Uani 1 1 d . . . . .
O4 O 0.98811(10) 0.73774(13) 0.94492(10) 0.0213(3) Uani 1 1 d . . . . .
O5 O 0.87634(11) 0.60663(12) 0.96004(10) 0.0233(3) Uani 1 1 d . . . . .
N1 N 0.68766(12) 0.65551(15) 0.56861(12) 0.0173(3) Uani 1 1 d . . . . .
N2 N 0.84639(11) 0.61942(13) 0.73815(11) 0.0138(3) Uani 1 1 d . . . . .
C1 C 0.32926(16) 0.5913(2) 0.24706(17) 0.0193(5) Uani 0.8353(10) 1 d D . P A 1
H1A H 0.272874 0.552451 0.247294 0.023 Uiso 0.8353(10) 1 calc R U P A 1
C2 C 0.40872(18) 0.7102(2) 0.16682(17) 0.0127(4) Uani 0.8353(10) 1 d D . P A 1
C3 C 0.3243(3) 0.6501(2) 0.1663(2) 0.0154(5) Uani 0.8353(10) 1 d D . P A 1
C4 C 0.2371(2) 0.6525(3) 0.0838(2) 0.0232(7) Uani 0.8353(10) 1 d D . P A 1
H4 H 0.180613 0.612428 0.082369 0.028 Uiso 0.8353(10) 1 calc R U P A 1
C5 C 0.2327(2) 0.7114(6) 0.0064(3) 0.0235(8) Uani 0.8353(10) 1 d D . P A 1
H5 H 0.173240 0.712613 -0.048036 0.028 Uiso 0.8353(10) 1 calc R U P A 1
C6 C 0.3165(2) 0.7705(2) 0.00697(19) 0.0221(6) Uani 0.8353(10) 1 d D . P A 1
H6 H 0.313490 0.809604 -0.047694 0.026 Uiso 0.8353(10) 1 calc R U P A 1
C7 C 0.40210(17) 0.7717(2) 0.08588(18) 0.0171(3) Uani 0.8353(10) 1 d D . P A 1
H7 H 0.457170 0.814047 0.086256 0.021 Uiso 0.8353(10) 1 calc R U P A 1
C8 C 0.49615(15) 0.70432(19) 0.25119(16) 0.0138(4) Uani 0.8353(10) 1 d D . P A
1
C9 C 0.50075(18) 0.6455(2) 0.32930(16) 0.0136(4) Uani 0.8353(10) 1 d D . P A 1
C10 C 0.41484(17) 0.5900(2) 0.32518(19) 0.0171(3) Uani 0.8353(10) 1 d D . P A 1
H10 H 0.416287 0.549831 0.378902 0.021 Uiso 0.8353(10) 1 calc R U P A 1
C11 C 0.59200(15) 0.63951(18) 0.41705(14) 0.0212(4) Uani 1 1 d D . . . .
C12 C 0.67913(13) 0.57170(17) 0.43733(13) 0.0166(4) Uani 1 1 d . . . . .
C13 C 0.73646(13) 0.58239(16) 0.53326(13) 0.0146(4) Uani 1 1 d . . . . .
C14 C 0.60124(15) 0.69022(18) 0.49972(14) 0.0216(4) Uani 1 1 d . . . . .
H14 H 0.555088 0.741170 0.507772 0.026 Uiso 1 1 calc R U . . .
C15 C 0.70842(14) 0.50622(17) 0.37191(13) 0.0163(4) Uani 1 1 d . . . . .
C16 C 0.65684(15) 0.44133(19) 0.21484(13) 0.0210(4) Uani 1 1 d . . . . .
H16A H 0.670475 0.358945 0.228039 0.025 Uiso 1 1 calc R U . . .
H16B H 0.715703 0.477659 0.210998 0.025 Uiso 1 1 calc R U . . .
C17 C 0.56851(17) 0.4577(2) 0.12430(15) 0.0304(5) Uani 1 1 d . . . . .
H17A H 0.581324 0.422614 0.072862 0.046 Uiso 1 1 calc R U . . .
H17B H 0.556017 0.539554 0.112041 0.046 Uiso 1 1 calc R U . . .
H17C H 0.510821 0.421608 0.129181 0.046 Uiso 1 1 calc R U . . .
C18 C 0.82674(13) 0.52514(16) 0.59202(13) 0.0139(4) Uani 1 1 d . . . . .
H18 H 0.853710 0.472190 0.562142 0.017 Uiso 1 1 calc R U . . .
C19 C 0.87583(13) 0.53980(16) 0.68456(13) 0.0137(4) Uani 1 1 d . . . . .
C20 C 0.96821(13) 0.47409(16) 0.74728(13) 0.0145(4) Uani 1 1 d . . . . .
C21 C 0.98817(14) 0.52632(18) 0.84435(14) 0.0213(4) Uani 1 1 d . . . . .
H21A H 0.984571 0.467358 0.888624 0.026 Uiso 1 1 calc R U . . .
H21B H 1.053668 0.563327 0.870800 0.026 Uiso 1 1 calc R U . . .
C22 C 0.90740(13) 0.61253(16) 0.82414(13) 0.0145(4) Uani 1 1 d . . . . .
C23 C 1.05435(14) 0.4952(2) 0.71756(15) 0.0241(4) Uani 1 1 d . . . . .
H23A H 1.036948 0.467504 0.653480 0.036 Uiso 1 1 calc R U . . .
H23B H 1.112747 0.454470 0.760054 0.036 Uiso 1 1 calc R U . . .
H23C H 1.068420 0.577292 0.720141 0.036 Uiso 1 1 calc R U . . .
C24 C 0.94741(15) 0.34574(17) 0.74485(15) 0.0229(4) Uani 1 1 d . . . . .
H24A H 0.892109 0.332229 0.763477 0.034 Uiso 1 1 calc R U . . .
H24B H 1.005984 0.306097 0.788256 0.034 Uiso 1 1 calc R U . . .
H24C H 0.930831 0.316737 0.681243 0.034 Uiso 1 1 calc R U . . .
C25 C 0.89690(13) 0.68384(16) 0.89999(12) 0.0149(4) Uani 1 1 d . . . . .
H25 H 0.842833 0.741182 0.873290 0.018 Uiso 1 1 calc R U . . .
C26 C 0.98921(15) 0.82259(18) 1.01173(14) 0.0214(4) Uani 1 1 d . . . . .
H26A H 0.937769 0.879334 0.981201 0.032 Uiso 1 1 calc R U . . .
H26B H 1.053600 0.860355 1.036700 0.032 Uiso 1 1 calc R U . . .
H26C H 0.977025 0.786178 1.063027 0.032 Uiso 1 1 calc R U . . .
C27 C 0.80451(16) 0.6404(2) 0.99470(16) 0.0278(5) Uani 1 1 d . . . . .
H27A H 0.758716 0.694661 0.951021 0.042 Uiso 1 1 calc R U . . .
H27B H 0.837130 0.676854 1.056023 0.042 Uiso 1 1 calc R U . . .
H27C H 0.768119 0.573085 1.000971 0.042 Uiso 1 1 calc R U . . .
C10A C 0.5603(9) 0.7664(10) 0.2653(8) 0.0193(5) Uani 0.1647(10) 1 d D . P A 2
H10A H 0.623586 0.800869 0.291293 0.023 Uiso 0.1647(10) 1 calc R U P A 2
C7A C 0.2780(11) 0.6223(12) 0.1511(11) 0.026(3) Uani 0.1647(10) 1 d D . P A 2
H7A H 0.256701 0.572134 0.187496 0.031 Uiso 0.1647(10) 1 calc R U P A 2
C5A C 0.2516(16) 0.714(3) 0.0028(16) 0.0235(8) Uani 0.1647(10) 1 d D . P A 2
H5A H 0.213617 0.719227 -0.062583 0.028 Uiso 0.1647(10) 1 calc R U P A 2
C3A C 0.4046(8) 0.7459(10) 0.1320(10) 0.0139(15) Uani 0.1647(10) 1 d D . P A 2
C8A C 0.4405(8) 0.6467(10) 0.2841(7) 0.018(2) Uani 0.1647(10) 1 d D . P A 2
C2A C 0.3722(10) 0.6711(11) 0.1883(8) 0.0139(15) Uani 0.1647(10) 1 d D . P A 2
C6A C 0.2177(15) 0.649(2) 0.0612(13) 0.0235(8) Uani 0.1647(10) 1 d D . P A 2
H6A H 0.151496 0.622797 0.037069 0.028 Uiso 0.1647(10) 1 calc R U P A 2
C9A C 0.5340(8) 0.6907(9) 0.3210(7) 0.0139(15) Uani 0.1647(10) 1 d D . P A 2
C4A C 0.3385(12) 0.7692(15) 0.0416(10) 0.0221(6) Uani 0.1647(10) 1 d D . P A 2
H4A H 0.354895 0.825422 0.006010 0.026 Uiso 0.1647(10) 1 calc R U P A 2
C1A C 0.4989(9) 0.7940(10) 0.1739(8) 0.026(3) Uani 0.1647(10) 1 d D . P A 2
H1AA H 0.520943 0.846157 0.139405 0.031 Uiso 0.1647(10) 1 calc R U P A 2
Br1A Br 0.40302(9) 0.55132(12) 0.36195(10) 0.0237(5) Uani 0.1647(10) 1 d D . P
A 2
H1 H 0.7112(18) 0.673(2) 0.6253(19) 0.026(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C8 1.902(2) . ?
O2 C15 1.348(2) . ?
O2 C16 1.451(2) . ?
O3 C15 1.211(2) . ?
O4 C25 1.401(2) . ?
O4 C26 1.431(2) . ?
O5 C25 1.414(2) . ?
O5 C27 1.421(2) . ?
N1 C13 1.365(2) . ?
N1 C14 1.366(2) . ?
N1 H1 0.84(3) . ?
N2 C19 1.426(2) . ?
N2 C22 1.287(2) . ?
C1 H1A 0.9500 . ?
C1 C3 1.407(3) . ?
C1 C10 1.366(3) . ?
C2 C3 1.429(4) . ?
C2 C7 1.418(3) . ?
C2 C8 1.436(3) . ?
C3 C4 1.416(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.365(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.414(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.373(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.373(3) . ?
C9 C10 1.404(4) . ?
C9 C11 1.496(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.437(3) . ?
C11 C14 1.371(3) . ?
C11 C9A 1.522(10) . ?
C12 C13 1.401(3) . ?
C12 C15 1.466(3) . ?
C13 C18 1.451(2) . ?
C14 H14 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.509(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 0.9500 . ?
C18 C19 1.342(3) . ?
C19 C20 1.536(2) . ?
C20 C21 1.544(3) . ?
C20 C23 1.534(3) . ?
C20 C24 1.531(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.498(3) . ?
C22 C25 1.500(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C10A H10A 0.9500 . ?
C10A C9A 1.394(13) . ?
C10A C1A 1.390(13) . ?
C7A H7A 0.9500 . ?
C7A C2A 1.402(14) . ?
C7A C6A 1.365(15) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.418(19) . ?
C5A C4A 1.348(18) . ?
C3A C2A 1.444(14) . ?
C3A C4A 1.387(14) . ?
C3A C1A 1.402(13) . ?
C8A C2A 1.461(13) . ?
C8A C9A 1.371(12) . ?
C8A Br1A 1.881(10) . ?
C6A H6A 0.9500 . ?
C4A H4A 0.9500 . ?
C1A H1AA 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
C15 O2 C16 116.17(15) . . ?
C25 O4 C26 114.14(15) . . ?
C25 O5 C27 117.17(15) . . ?
C13 N1 C14 110.48(16) . . ?
C13 N1 H1 120.7(17) . . ?
C14 N1 H1 128.8(17) . . ?
C22 N2 C19 108.33(15) . . ?
C3 C1 H1A 119.9 . . ?
C10 C1 H1A 119.9 . . ?
C10 C1 C3 120.3(3) . . ?
C3 C2 C8 116.9(2) . . ?
C7 C2 C3 119.2(2) . . ?
C7 C2 C8 123.9(2) . . ?
C1 C3 C2 119.7(3) . . ?
C1 C3 C4 121.8(3) . . ?
C4 C3 C2 118.5(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.1(3) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.3(2) . . ?
C6 C7 H7 119.8 . . ?
C2 C8 Br1 118.39(18) . . ?
C9 C8 Br1 118.55(17) . . ?
C9 C8 C2 123.1(2) . . ?
C8 C9 C10 117.4(2) . . ?
C8 C9 C11 122.9(2) . . ?
C10 C9 C11 119.7(2) . . ?
C1 C10 C9 122.7(3) . . ?
C1 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C12 C11 C9 129.39(19) . . ?
C12 C11 C9A 122.9(4) . . ?
C14 C11 C9 123.77(18) . . ?
C14 C11 C12 106.36(17) . . ?
C14 C11 C9A 123.9(5) . . ?
C11 C12 C15 128.20(17) . . ?
C13 C12 C11 107.43(17) . . ?
C13 C12 C15 124.31(17) . . ?
N1 C13 C12 106.81(16) . . ?
N1 C13 C18 122.46(17) . . ?
C12 C13 C18 130.59(17) . . ?
N1 C14 C11 108.89(17) . . ?
N1 C14 H14 125.6 . . ?
C11 C14 H14 125.6 . . ?
O2 C15 C12 111.63(16) . . ?
O3 C15 O2 122.98(18) . . ?
O3 C15 C12 125.37(17) . . ?
O2 C16 H16A 110.4 . . ?
O2 C16 H16B 110.4 . . ?
O2 C16 C17 106.80(16) . . ?
H16A C16 H16B 108.6 . . ?
C17 C16 H16A 110.4 . . ?
C17 C16 H16B 110.4 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C18 H18 116.9 . . ?
C19 C18 C13 126.25(17) . . ?
C19 C18 H18 116.9 . . ?
N2 C19 C20 110.83(15) . . ?
C18 C19 N2 123.21(16) . . ?
C18 C19 C20 125.95(17) . . ?
C19 C20 C21 101.70(14) . . ?
C23 C20 C19 111.32(15) . . ?
C23 C20 C21 111.48(16) . . ?
C24 C20 C19 110.86(15) . . ?
C24 C20 C21 111.87(16) . . ?
C24 C20 C23 109.45(17) . . ?
C20 C21 H21A 111.1 . . ?
C20 C21 H21B 111.1 . . ?
H21A C21 H21B 109.1 . . ?
C22 C21 C20 103.33(15) . . ?
C22 C21 H21A 111.1 . . ?
C22 C21 H21B 111.1 . . ?
N2 C22 C21 115.80(17) . . ?
N2 C22 C25 122.23(17) . . ?
C21 C22 C25 121.94(16) . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O4 C25 O5 111.87(15) . . ?
O4 C25 C22 105.46(15) . . ?
O4 C25 H25 111.1 . . ?
O5 C25 C22 106.07(15) . . ?
O5 C25 H25 111.1 . . ?
C22 C25 H25 111.1 . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O5 C27 H27A 109.5 . . ?
O5 C27 H27B 109.5 . . ?
O5 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C9A C10A H10A 118.3 . . ?
C1A C10A H10A 118.3 . . ?
C1A C10A C9A 123.4(11) . . ?
C2A C7A H7A 120.9 . . ?
C6A C7A H7A 120.9 . . ?
C6A C7A C2A 118.2(15) . . ?
C6A C5A H5A 120.5 . . ?
C4A C5A H5A 120.5 . . ?
C4A C5A C6A 119.0(18) . . ?
C4A C3A C2A 117.5(11) . . ?
C4A C3A C1A 124.6(13) . . ?
C1A C3A C2A 117.8(11) . . ?
C2A C8A Br1A 120.8(8) . . ?
C9A C8A C2A 122.1(10) . . ?
C9A C8A Br1A 117.1(7) . . ?
C7A C2A C3A 120.6(11) . . ?
C7A C2A C8A 121.1(12) . . ?
C3A C2A C8A 118.3(11) . . ?
C7A C6A C5A 121.6(17) . . ?
C7A C6A H6A 119.2 . . ?
C5A C6A H6A 119.2 . . ?
C10A C9A C11 132.1(9) . . ?
C8A C9A C11 110.4(8) . . ?
C8A C9A C10A 117.4(9) . . ?
C5A C4A C3A 121.8(15) . . ?
C5A C4A H4A 119.1 . . ?
C3A C4A H4A 119.1 . . ?
C10A C1A C3A 120.8(11) . . ?
C10A C1A H1AA 119.6 . . ?
C3A C1A H1AA 119.6 . . ?

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 C8 C9 C10 178.92(17) . . . . ?
Br1 C8 C9 C11 -0.5(3) . . . . ?
N1 C13 C18 C19 -3.7(3) . . . . ?
N2 C19 C20 C21 0.06(19) . . . . ?
N2 C19 C20 C23 -118.77(18) . . . . ?
N2 C19 C20 C24 119.13(17) . . . . ?
N2 C22 C25 O4 -127.07(18) . . . . ?
N2 C22 C25 O5 114.13(19) . . . . ?
C1 C3 C4 C5 178.9(4) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C2 C8 C9 C10 -0.6(3) . . . . ?
C2 C8 C9 C11 180.0(2) . . . . ?
C3 C1 C10 C9 -0.1(4) . . . . ?
C3 C2 C7 C6 -2.0(4) . . . . ?
C3 C2 C8 Br1 179.82(16) . . . . ?
C3 C2 C8 C9 -0.7(3) . . . . ?
C3 C4 C5 C6 0.7(8) . . . . ?
C4 C5 C6 C7 -1.7(7) . . . . ?
C5 C6 C7 C2 2.3(5) . . . . ?
C7 C2 C3 C1 -178.3(2) . . . . ?
C7 C2 C3 C4 1.1(4) . . . . ?
C7 C2 C8 Br1 -0.3(3) . . . . ?
C7 C2 C8 C9 179.2(2) . . . . ?
C8 C2 C3 C1 1.6(3) . . . . ?
C8 C2 C3 C4 -179.1(3) . . . . ?
C8 C2 C7 C6 178.1(2) . . . . ?
C8 C9 C10 C1 1.0(4) . . . . ?
C8 C9 C11 C12 -77.2(3) . . . . ?
C8 C9 C11 C14 111.9(3) . . . . ?
C9 C11 C12 C13 -170.5(2) . . . . ?
C9 C11 C12 C15 12.1(4) . . . . ?
C9 C11 C14 N1 171.7(2) . . . . ?
C10 C1 C3 C2 -1.2(4) . . . . ?
C10 C1 C3 C4 179.5(3) . . . . ?
C10 C9 C11 C12 103.4(3) . . . . ?
C10 C9 C11 C14 -67.6(3) . . . . ?
C11 C9 C10 C1 -179.5(2) . . . . ?
C11 C12 C13 N1 -1.6(2) . . . . ?
C11 C12 C13 C18 174.10(19) . . . . ?
C11 C12 C15 O2 -13.4(3) . . . . ?
C11 C12 C15 O3 165.1(2) . . . . ?
C12 C11 C14 N1 -1.0(2) . . . . ?
C12 C11 C9A C10A -59.0(14) . . . . ?
C12 C11 C9A C8A 117.5(8) . . . . ?
C12 C13 C18 C19 -178.7(2) . . . . ?
C13 N1 C14 C11 0.1(2) . . . . ?
C13 C12 C15 O2 169.65(18) . . . . ?
C13 C12 C15 O3 -11.9(3) . . . . ?
C13 C18 C19 N2 -2.5(3) . . . . ?
C13 C18 C19 C20 176.40(17) . . . . ?
C14 N1 C13 C12 1.0(2) . . . . ?
C14 N1 C13 C18 -175.13(18) . . . . ?
C14 C11 C12 C13 1.6(2) . . . . ?
C14 C11 C12 C15 -175.8(2) . . . . ?
C14 C11 C9A C10A 88.1(13) . . . . ?
C14 C11 C9A C8A -95.4(9) . . . . ?
C15 O2 C16 C17 -169.34(18) . . . . ?
C15 C12 C13 N1 175.95(18) . . . . ?
C15 C12 C13 C18 -8.4(3) . . . . ?
C16 O2 C15 O3 -4.6(3) . . . . ?
C16 O2 C15 C12 173.85(16) . . . . ?
C18 C19 C20 C21 -178.93(19) . . . . ?
C18 C19 C20 C23 62.2(2) . . . . ?
C18 C19 C20 C24 -59.9(2) . . . . ?
C19 N2 C22 C21 -0.7(2) . . . . ?
C19 N2 C22 C25 -179.03(16) . . . . ?
C19 C20 C21 C22 -0.39(19) . . . . ?
C20 C21 C22 N2 0.7(2) . . . . ?
C20 C21 C22 C25 179.05(16) . . . . ?
C21 C22 C25 O4 54.7(2) . . . . ?
C21 C22 C25 O5 -64.1(2) . . . . ?
C22 N2 C19 C18 179.39(18) . . . . ?
C22 N2 C19 C20 0.4(2) . . . . ?
C23 C20 C21 C22 118.32(18) . . . . ?
C24 C20 C21 C22 -118.75(17) . . . . ?
C26 O4 C25 O5 -73.4(2) . . . . ?
C26 O4 C25 C22 171.75(16) . . . . ?
C27 O5 C25 O4 106.2(2) . . . . ?
C27 O5 C25 C22 -139.29(17) . . . . ?
C2A C7A C6A C5A 6(4) . . . . ?
C2A C3A C4A C5A -8(3) . . . . ?
C2A C3A C1A C10A 2.8(18) . . . . ?
C2A C8A C9A C11 -173.1(10) . . . . ?
C2A C8A C9A C10A 4.0(18) . . . . ?
C6A C7A C2A C3A -1(2) . . . . ?
C6A C7A C2A C8A 179.9(16) . . . . ?
C6A C5A C4A C3A 13(5) . . . . ?
C9A C11 C12 C13 153.7(5) . . . . ?
C9A C11 C12 C15 -23.7(6) . . . . ?
C9A C11 C14 N1 -152.7(5) . . . . ?
C9A C10A C1A C3A 0(2) . . . . ?
C9A C8A C2A C7A 178.0(13) . . . . ?
C9A C8A C2A C3A -1.2(18) . . . . ?
C4A C5A C6A C7A -13(5) . . . . ?
C4A C3A C2A C7A 2(2) . . . . ?
C4A C3A C2A C8A -179.3(13) . . . . ?
C4A C3A C1A C10A 179.6(14) . . . . ?
C1A C10A C9A C11 172.8(11) . . . . ?
C1A C10A C9A C8A -3.5(19) . . . . ?
C1A C3A C2A C7A 178.6(12) . . . . ?
C1A C3A C2A C8A -2.2(17) . . . . ?
C1A C3A C4A C5A 175(2) . . . . ?
Br1A C8A C2A C7A -1.5(17) . . . . ?
Br1A C8A C2A C3A 179.4(9) . . . . ?
Br1A C8A C9A C11 6.4(12) . . . . ?
Br1A C8A C9A C10A -176.6(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
