# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_26NBP_190717
_database_code_depnum_ccdc_archive 'CCDC 2156271'
loop_
_audit_author_name
_audit_author_address
'Alexandre N. Sobolev'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2022-03-04 deposited with the CCDC.	2022-05-24 downloaded from the CCDC.
;

#==============================================================================


# 6. CRYSTALLOGRAPHY

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H44 N2, 2(Br), 2(H2 O)'
_chemical_formula_sum            'C28 H48 Br2 N2 O2'
_chemical_formula_weight         604.50

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.8287(2)
_cell_length_b                   9.7039(3)
_cell_length_c                   16.4007(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.677(3)
_cell_angle_gamma                90
_cell_volume                     1402.20(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5367
_cell_measurement_theta_min      2.450
_cell_measurement_theta_max      29.107
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0176435
_diffrn_orient_matrix_UB_12      0.0184040
_diffrn_orient_matrix_UB_13      0.0401628
_diffrn_orient_matrix_UB_21      0.0550641
_diffrn_orient_matrix_UB_22      0.0532621
_diffrn_orient_matrix_UB_23      0.0003391
_diffrn_orient_matrix_UB_31      -0.0560224
_diffrn_orient_matrix_UB_32      0.0465387
_diffrn_orient_matrix_UB_33      -0.0162841

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.246
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.101
_exptl_absorpt_coefficient_mu    2.918
_shelx_estimated_absorpt_T_min   0.534
_shelx_estimated_absorpt_T_max   0.757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9008
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4738
_diffrn_reflns_number            11801
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.440
_diffrn_reflns_theta_max         29.254
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3450
_reflns_number_gt                2828
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'X-Seed v. 4.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0250P)²+0.8800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3450
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0676
_refine_ls_wR_factor_gt          0.0615
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.48238(2) 0.00920(2) 0.66227(2) 0.01697(7) Uani 1 1 d . . . . .
O1W O 0.27356(19) 0.0347(2) 0.48507(11) 0.0314(4) Uani 1 1 d . . . . .
H1WA H 0.322(3) 0.031(3) 0.530(2) 0.046(9) Uiso 1 1 d . . . . .
H1WB H 0.340(4) 0.017(3) 0.451(2) 0.068(11) Uiso 1 1 d . . . . .
N1 N 0.49868(18) 0.58300(17) 0.20369(10) 0.0155(4) Uani 1 1 d . . . . .
C1 C 0.5428(2) 0.6195(2) 0.41515(12) 0.0156(4) Uani 1 1 d . . . . .
H1A H 0.546498 0.715865 0.405231 0.019 Uiso 1 1 calc R U . . .
C2 C 0.5770(2) 0.5294(2) 0.35415(12) 0.0154(4) Uani 1 1 d . . . . .
C3 C 0.5750(2) 0.3858(2) 0.37052(12) 0.0162(4) Uani 1 1 d . . . . .
H3A H 0.600956 0.322837 0.329327 0.019 Uiso 1 1 calc R U . . .
C4 C 0.5364(2) 0.3364(2) 0.44464(12) 0.0163(4) Uani 1 1 d . . . . .
H4A H 0.535380 0.239826 0.454100 0.020 Uiso 1 1 calc R U . . .
C5 C 0.4978(2) 0.4284(2) 0.50753(11) 0.0147(4) Uani 1 1 d . . . . .
C6 C 0.6227(2) 0.5846(2) 0.27331(12) 0.0161(4) Uani 1 1 d . . . . .
H6A H 0.709835 0.529790 0.256209 0.019 Uiso 1 1 calc R U . . .
H6B H 0.658159 0.680658 0.281487 0.019 Uiso 1 1 calc R U . . .
C7 C 0.5606(2) 0.6539(2) 0.12915(12) 0.0180(4) Uani 1 1 d . . . . .
H7A H 0.672644 0.647706 0.131004 0.022 Uiso 1 1 calc R U . . .
H7B H 0.518183 0.611107 0.077849 0.022 Uiso 1 1 calc R U . . .
C8 C 0.5103(2) 0.8017(2) 0.13472(13) 0.0226(5) Uani 1 1 d . . . . .
H8A H 0.511979 0.848897 0.081282 0.027 Uiso 1 1 calc R U . . .
H8B H 0.574269 0.853305 0.176005 0.027 Uiso 1 1 calc R U . . .
C9 C 0.3476(2) 0.7847(2) 0.16096(13) 0.0234(5) Uani 1 1 d . . . . .
H9A H 0.309536 0.871659 0.183677 0.028 Uiso 1 1 calc R U . . .
H9B H 0.278040 0.755210 0.114493 0.028 Uiso 1 1 calc R U . . .
C10 C 0.3637(2) 0.6736(2) 0.22591(12) 0.0184(4) Uani 1 1 d . . . . .
H10A H 0.269720 0.617892 0.226148 0.022 Uiso 1 1 calc R U . . .
H10B H 0.383744 0.715155 0.280655 0.022 Uiso 1 1 calc R U . . .
C11 C 0.4436(2) 0.4395(2) 0.18185(12) 0.0173(4) Uani 1 1 d . . . . .
H11A H 0.352675 0.446673 0.143508 0.021 Uiso 1 1 calc R U . . .
H11B H 0.412539 0.393447 0.231997 0.021 Uiso 1 1 calc R U . . .
C12 C 0.5613(2) 0.3495(2) 0.14297(13) 0.0199(4) Uani 1 1 d . . . . .
H12A H 0.581499 0.387376 0.088688 0.024 Uiso 1 1 calc R U . . .
H12B H 0.657523 0.351950 0.177458 0.024 Uiso 1 1 calc R U . . .
C13 C 0.5084(2) 0.2005(2) 0.13317(13) 0.0235(5) Uani 1 1 d . . . . .
H13A H 0.587162 0.147335 0.106436 0.028 Uiso 1 1 calc R U . . .
H13B H 0.498514 0.160317 0.188057 0.028 Uiso 1 1 calc R U . . .
C14 C 0.3595(2) 0.1844(2) 0.08388(14) 0.0262(5) Uani 1 1 d . . . . .
H14A H 0.338823 0.086250 0.074345 0.039 Uiso 1 1 calc R U . . .
H14B H 0.364830 0.231624 0.031338 0.039 Uiso 1 1 calc R U . . .
H14C H 0.277875 0.224728 0.113908 0.039 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
O1W H1WA 0.83(3) . ?
O1W H1WB 0.85(4) . ?
N1 C11 1.511(3) . ?
N1 C6 1.531(2) . ?
N1 C7 1.534(2) . ?
N1 C10 1.543(2) . ?
C1 C2 1.377(3) . ?
C1 C5 1.418(3) 3_666 ?
C1 H1A 0.9500 . ?
C2 C3 1.419(3) . ?
C2 C6 1.509(3) . ?
C3 C4 1.370(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.422(3) . ?
C4 H4A 0.9500 . ?
C5 C5 1.412(4) 3_666 ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.505(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.534(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.516(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.528(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.525(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.507(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
H1WA O1W H1WB 103(3) . . ?
C11 N1 C6 112.95(15) . . ?
C11 N1 C7 110.51(14) . . ?
C6 N1 C7 108.41(14) . . ?
C11 N1 C10 109.83(14) . . ?
C6 N1 C10 110.17(15) . . ?
C7 N1 C10 104.64(15) . . ?
C2 C1 C5 121.43(18) . 3_666 ?
C2 C1 H1A 119.3 . . ?
C5 C1 H1A 119.3 3_666 . ?
C1 C2 C3 118.69(18) . . ?
C1 C2 C6 119.80(18) . . ?
C3 C2 C6 121.45(18) . . ?
C4 C3 C2 121.22(18) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 . . ?
C3 C4 C5 120.56(19) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C5 C5 C1 119.4(2) 3_666 3_666 ?
C5 C5 C4 118.7(2) 3_666 . ?
C1 C5 C4 121.92(18) 3_666 . ?
C2 C6 N1 115.67(15) . . ?
C2 C6 H6A 108.4 . . ?
N1 C6 H6A 108.4 . . ?
C2 C6 H6B 108.4 . . ?
N1 C6 H6B 108.4 . . ?
H6A C6 H6B 107.4 . . ?
C8 C7 N1 104.92(16) . . ?
C8 C7 H7A 110.8 . . ?
N1 C7 H7A 110.8 . . ?
C8 C7 H7B 110.8 . . ?
N1 C7 H7B 110.8 . . ?
H7A C7 H7B 108.8 . . ?
C7 C8 C9 101.53(17) . . ?
C7 C8 H8A 111.5 . . ?
C9 C8 H8A 111.5 . . ?
C7 C8 H8B 111.5 . . ?
C9 C8 H8B 111.5 . . ?
H8A C8 H8B 109.3 . . ?
C10 C9 C8 103.09(16) . . ?
C10 C9 H9A 111.1 . . ?
C8 C9 H9A 111.1 . . ?
C10 C9 H9B 111.1 . . ?
C8 C9 H9B 111.1 . . ?
H9A C9 H9B 109.1 . . ?
C9 C10 N1 106.13(15) . . ?
C9 C10 H10A 110.5 . . ?
N1 C10 H10A 110.5 . . ?
C9 C10 H10B 110.5 . . ?
N1 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
N1 C11 C12 114.13(16) . . ?
N1 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
N1 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 111.98(17) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 113.94(18) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C5 C1 C2 C3 -1.7(3) 3_666 . . . ?
C5 C1 C2 C6 -178.77(17) 3_666 . . . ?
C1 C2 C3 C4 1.6(3) . . . . ?
C6 C2 C3 C4 178.66(17) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C5 -0.9(3) . . . 3_666 ?
C3 C4 C5 C1 179.95(18) . . . 3_666 ?
C1 C2 C6 N1 -101.3(2) . . . . ?
C3 C2 C6 N1 81.7(2) . . . . ?
C11 N1 C6 C2 -62.2(2) . . . . ?
C7 N1 C6 C2 175.03(16) . . . . ?
C10 N1 C6 C2 61.1(2) . . . . ?
C11 N1 C7 C8 141.73(16) . . . . ?
C6 N1 C7 C8 -93.99(18) . . . . ?
C10 N1 C7 C8 23.56(19) . . . . ?
N1 C7 C8 C9 -41.33(19) . . . . ?
C7 C8 C9 C10 43.3(2) . . . . ?
C8 C9 C10 N1 -28.9(2) . . . . ?
C11 N1 C10 C9 -114.93(17) . . . . ?
C6 N1 C10 C9 120.04(17) . . . . ?
C7 N1 C10 C9 3.7(2) . . . . ?
C6 N1 C11 C12 -67.9(2) . . . . ?
C7 N1 C11 C12 53.7(2) . . . . ?
C10 N1 C11 C12 168.66(16) . . . . ?
N1 C11 C12 C13 171.97(16) . . . . ?
C11 C12 C13 C14 56.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1W H1WA Br1 0.83(3) 2.52(3) 3.3495(18) 176(3) . yes
O1W H1WB Br1 0.85(4) 2.52(4) 3.3663(18) 172(3) 3_656 yes
C6 H6A Br1 0.99 2.96 3.8689(19) 152.5 4_665 yes
C8 H8B Br1 0.99 3.04 3.799(2) 134.5 3_666 yes
C10 H10A Br1 0.99 2.95 3.888(2) 158.1 4_565 yes
C10 H10B Br1 0.99 3.05 3.791(2) 132.8 3_666 yes
C11 H11A O1W 0.99 2.47 3.369(3) 150.3 2 yes
C12 H12A O1W 0.99 2.59 3.479(3) 149.5 4_665 yes

_refine_diff_density_max         0.487
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.078



####################################################################### 
# 
# 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_26NMI
_database_code_depnum_ccdc_archive 'CCDC 2156269'
loop_
_audit_author_name
_audit_author_address
'Alexandre N. Sobolev'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2022-03-24 deposited with the CCDC.	2022-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N4, 2(Br), 2(H2 O)'
_chemical_formula_sum            'C20 H26 Br2 N4 O2'
_chemical_formula_weight         514.27

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'
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.8271(11)
_cell_length_b                   13.4405(14)
_cell_length_c                   18.040(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2140.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1772
_cell_measurement_theta_min      4.885
_cell_measurement_theta_max      67.072
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0136111
_diffrn_orient_matrix_UB_12      0.0019095
_diffrn_orient_matrix_UB_13      -0.0851562
_diffrn_orient_matrix_UB_21      -0.1689770
_diffrn_orient_matrix_UB_22      -0.0270464
_diffrn_orient_matrix_UB_23      0.0062847
_diffrn_orient_matrix_UB_31      -0.0412517
_diffrn_orient_matrix_UB_32      0.1113490
_diffrn_orient_matrix_UB_33      0.0028992

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    4.993
_shelx_estimated_absorpt_T_min   0.358
_shelx_estimated_absorpt_T_max   0.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.50311
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 10.4738
_diffrn_reflns_number            8397
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_av_R_equivalents  0.1061
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         6.482
_diffrn_reflns_theta_max         67.457
_diffrn_reflns_theta_full        67.457
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1906
_reflns_number_gt                1291
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2015)'
_computing_molecular_graphics    'X-Seed v. 4.0 (Barbour, 2020)'
_computing_publication_material  'SHELXL-2019/2 (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0850P)²+41.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1906
_refine_ls_number_parameters     134
_refine_ls_number_restraints     100
_refine_ls_R_factor_all          0.1382
_refine_ls_R_factor_gt           0.1041
_refine_ls_wR_factor_ref         0.2709
_refine_ls_wR_factor_gt          0.2452
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.08534(17) 0.34477(10) 0.32847(7) 0.0572(5) Uani 1 1 d . . . . .
O1 O 0.4178(11) 0.2334(8) 0.3144(6) 0.068(3) Uani 1 1 d D . . . .
H1A H 0.331(5) 0.259(7) 0.307(5) 0.082 Uiso 1 1 d D U . . .
H1B H 0.473(7) 0.244(10) 0.277(3) 0.082 Uiso 1 1 d D U . . .
N1 N 0.7459(13) 0.1909(7) 0.4447(5) 0.050(2) Uani 1 1 d . . . . .
N2 N 0.7011(14) 0.0970(8) 0.3511(6) 0.064(3) Uani 1 1 d . . . . .
C1 C 0.5852(14) 0.3899(9) 0.4482(9) 0.080(4) Uani 1 1 d D . . . .
H1 H 0.573681 0.355233 0.402700 0.096 Uiso 1 1 calc R U . . .
C2 C 0.6861(11) 0.3618(6) 0.5001(7) 0.061(3) Uani 1 1 d D . . . .
C3 C 0.7006(12) 0.4132(8) 0.5707(6) 0.078(4) Uani 1 1 d D . . . .
H3 H 0.773426 0.390000 0.605407 0.093 Uiso 1 1 calc R U . . .
C4 C 0.6140(14) 0.4929(9) 0.5888(8) 0.075(4) Uani 1 1 d D . . . .
H4 H 0.624080 0.526708 0.634760 0.091 Uiso 1 1 calc R U . . .
C5 C 0.5055(12) 0.5226(8) 0.5333(4) 0.064(3) Uani 1 1 d D . . . .
C6 C 0.7984(13) 0.2729(8) 0.4913(7) 0.055(3) Uani 1 1 d . . . . .
H6A H 0.894360 0.298662 0.470321 0.066 Uiso 1 1 calc R U . . .
H6B H 0.821382 0.246256 0.541227 0.066 Uiso 1 1 calc R U . . .
C7 C 0.7738(17) 0.1791(10) 0.3740(7) 0.059(3) Uani 1 1 d . . . . .
H7 H 0.834806 0.221261 0.344079 0.071 Uiso 1 1 calc R U . . .
C8 C 0.6232(15) 0.0573(9) 0.4107(7) 0.052(3) Uani 1 1 d . . . . .
H8 H 0.561960 -0.000794 0.410102 0.062 Uiso 1 1 calc R U . . .
C9 C 0.6498(14) 0.1156(8) 0.4693(7) 0.047(2) Uani 1 1 d . . . . .
H9 H 0.610905 0.107278 0.518033 0.057 Uiso 1 1 calc R U . . .
C10 C 0.701(2) 0.0568(14) 0.2748(9) 0.094(6) Uani 1 1 d . U . . .
H10A H 0.772774 0.094668 0.244339 0.141 Uiso 1 1 calc R U . . .
H10B H 0.599287 0.062463 0.253706 0.141 Uiso 1 1 calc R U . . .
H10C H 0.731619 -0.013273 0.275909 0.141 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
O1 H1A 0.850(2) . ?
O1 H1B 0.850(2) . ?
N1 C7 1.310(16) . ?
N1 C9 1.394(16) . ?
N1 C6 1.462(15) . ?
N2 C7 1.341(17) . ?
N2 C8 1.384(16) . ?
N2 C10 1.478(18) . ?
C1 C2 1.346(14) . ?
C1 C5 1.460(12) 5_666 ?
C1 H1 0.9500 . ?
C2 C3 1.454(13) . ?
C2 C6 1.560(15) . ?
C3 C4 1.356(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.442(12) . ?
C4 H4 0.9500 . ?
C5 C5 1.350(14) 5_666 ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7 0.9500 . ?
C8 C9 1.336(17) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
H1A O1 H1B 108.6(7) . . ?
C7 N1 C9 109.7(10) . . ?
C7 N1 C6 126.3(11) . . ?
C9 N1 C6 123.9(10) . . ?
C7 N2 C8 108.4(11) . . ?
C7 N2 C10 125.9(12) . . ?
C8 N2 C10 125.7(11) . . ?
C2 C1 C5 115.5(12) . 5_666 ?
C2 C1 H1 122.3 . . ?
C5 C1 H1 122.3 5_666 . ?
C1 C2 C3 122.2(7) . . ?
C1 C2 C6 124.4(10) . . ?
C3 C2 C6 113.4(8) . . ?
C4 C3 C2 122.4(7) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C3 C4 C5 115.2(11) . . ?
C3 C4 H4 122.4 . . ?
C5 C4 H4 122.4 . . ?
C5 C5 C4 122.7(13) 5_666 . ?
C5 C5 C1 121.7(14) 5_666 5_666 ?
C4 C5 C1 115.4(8) . 5_666 ?
N1 C6 C2 115.7(10) . . ?
N1 C6 H6A 108.3 . . ?
C2 C6 H6A 108.3 . . ?
N1 C6 H6B 108.3 . . ?
C2 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
N1 C7 N2 108.1(12) . . ?
N1 C7 H7 126.0 . . ?
N2 C7 H7 126.0 . . ?
C9 C8 N2 107.6(11) . . ?
C9 C8 H8 126.2 . . ?
N2 C8 H8 126.2 . . ?
C8 C9 N1 106.3(11) . . ?
C8 C9 H9 126.8 . . ?
N1 C9 H9 126.8 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
C5 C1 C2 C3 1.8(10) 5_666 . . . ?
C5 C1 C2 C6 -177.9(10) 5_666 . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C6 C2 C3 C4 179.5(4) . . . . ?
C2 C3 C4 C5 0.5(6) . . . . ?
C3 C4 C5 C5 -2.6(14) . . . 5_666 ?
C3 C4 C5 C1 -178.4(10) . . . 5_666 ?
C7 N1 C6 C2 94.3(15) . . . . ?
C9 N1 C6 C2 -81.9(13) . . . . ?
C1 C2 C6 N1 -30.1(10) . . . . ?
C3 C2 C6 N1 150.2(9) . . . . ?
C9 N1 C7 N2 -1.1(16) . . . . ?
C6 N1 C7 N2 -177.7(12) . . . . ?
C8 N2 C7 N1 0.8(16) . . . . ?
C10 N2 C7 N1 179.6(15) . . . . ?
C7 N2 C8 C9 -0.2(16) . . . . ?
C10 N2 C8 C9 -179.0(15) . . . . ?
N2 C8 C9 N1 -0.4(14) . . . . ?
C7 N1 C9 C8 1.0(15) . . . . ?
C6 N1 C9 C8 177.7(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A Br1 0.850(2) 2.49(3) 3.304(10) 161(10) . yes
O1 H1B Br1 0.850(2) 2.53(6) 3.327(10) 156(11) 6_656 yes
C6 H6A Br1 0.99 3.13 3.997(12) 147.5 1_655 yes
C7 H7 Br1 0.95 2.78 3.633(14) 149.9 1_655 yes
C8 H8 Br1 0.95 2.86 3.708(13) 149.5 8_655 yes
C9 H9 Br1 0.95 2.85 3.730(12) 154.2 4_556 yes
C10 H10C Br1 0.98 3.13 3.892(19) 135.7 3_645 yes
C10 H10A O1 0.98 2.50 3.447(19) 162.9 6_656 yes

_refine_diff_density_max         1.451
_refine_diff_density_min         -1.112
_refine_diff_density_rms         0.156



####################################################################### 
# 
# 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_27NMI_190714
_database_code_depnum_ccdc_archive 'CCDC 2156270'
loop_
_audit_author_name
_audit_author_address
'Alexandre N. Sobolev'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2022-05-24 downloaded from the CCDC.
;

#==============================================================================


# 6. CRYSTALLOGRAPHY

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N4, 2(Br), H2 O'
_chemical_formula_sum            'C20 H24 Br2 N4 O'
_chemical_formula_weight         496.25

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.9774(2)
_cell_length_b                   9.2537(1)
_cell_length_c                   20.6183(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.240(1)
_cell_angle_gamma                90
_cell_volume                     2067.26(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16874
_cell_measurement_theta_min      2.416
_cell_measurement_theta_max      32.399
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0120919
_diffrn_orient_matrix_UB_12      0.0281519
_diffrn_orient_matrix_UB_13      0.0303206
_diffrn_orient_matrix_UB_21      -0.0535959
_diffrn_orient_matrix_UB_22      -0.0437348
_diffrn_orient_matrix_UB_23      -0.0023865
_diffrn_orient_matrix_UB_31      0.0356108
_diffrn_orient_matrix_UB_32      -0.0563047
_diffrn_orient_matrix_UB_33      0.0170143

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.113
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 3 -5 0.0621
-1 0 1 0.1032
0 1 1 0.1273
-5 3 4 0.0859
0 0 -1 0.0634
0 0 1 0.0492
-1 0 0 0.1056
1 0 0 0.1027
-4 -5 3 0.0977
1 0 -1 0.0963
3 -3 5 0.1055
_exptl_absorpt_coefficient_mu    3.939
_shelx_estimated_absorpt_T_min   0.362
_shelx_estimated_absorpt_T_max   0.665
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.460
_exptl_absorpt_correction_T_max  0.684
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4738
_diffrn_reflns_number            43743
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.418
_diffrn_reflns_theta_max         32.793
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7171
_reflns_number_gt                5962
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2015)'
_computing_molecular_graphics    'X-Seed v. 4.1 (Barbour, 2020)'
_computing_publication_material  'SHELXL-2019/2 (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²+1.2700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7171
_refine_ls_number_parameters     252
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0679
_refine_ls_wR_factor_gt          0.0629
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.22226(2) 0.10323(2) 0.44018(2) 0.02206(5) Uani 1 1 d . . . . .
Br2 Br 0.29131(2) 0.57756(2) 0.31559(2) 0.01650(4) Uani 1 1 d . . . . .
O1 O 0.25664(16) 0.45672(16) 0.46231(7) 0.0340(3) Uani 1 1 d D . . . .
H1A H 0.238(2) 0.3677(8) 0.4580(11) 0.051 Uiso 1 1 d D U . . .
H1B H 0.266(2) 0.490(2) 0.4249(5) 0.051 Uiso 1 1 d D U . . .
N1 N 0.55231(12) 0.25905(14) 0.34021(6) 0.0133(2) Uani 1 1 d . . . . .
N2 N 0.56741(13) 0.22475(16) 0.44491(7) 0.0171(3) Uani 1 1 d . . . . .
N3 N -0.03053(12) -0.17136(14) 0.30326(7) 0.0138(2) Uani 1 1 d . . . . .
N4 N 0.00241(12) -0.19437(15) 0.40874(7) 0.0157(3) Uani 1 1 d . . . . .
C1 C 0.33240(13) 0.15247(16) 0.26071(7) 0.0120(3) Uani 1 1 d . . . . .
H1 H 0.334529 0.154048 0.306950 0.014 Uiso 1 1 calc R U . . .
C2 C 0.41671(13) 0.23185(16) 0.23332(7) 0.0120(3) Uani 1 1 d . . . . .
C3 C 0.41158(14) 0.23389(17) 0.16423(8) 0.0145(3) Uani 1 1 d . . . . .
H3 H 0.469065 0.290649 0.145452 0.017 Uiso 1 1 calc R U . . .
C4 C 0.32435(14) 0.15465(17) 0.12419(8) 0.0152(3) Uani 1 1 d . . . . .
H4 H 0.321368 0.157834 0.077906 0.018 Uiso 1 1 calc R U . . .
C5 C 0.23861(14) 0.06804(16) 0.15134(7) 0.0126(3) Uani 1 1 d . . . . .
C6 C 0.14985(15) -0.01922(18) 0.11160(8) 0.0159(3) Uani 1 1 d . . . . .
H6 H 0.147465 -0.021038 0.065342 0.019 Uiso 1 1 calc R U . . .
C7 C 0.06781(15) -0.10062(17) 0.13924(8) 0.0158(3) Uani 1 1 d . . . . .
H7 H 0.008593 -0.157967 0.111997 0.019 Uiso 1 1 calc R U . . .
C8 C 0.07029(14) -0.10027(16) 0.20833(8) 0.0128(3) Uani 1 1 d . . . . .
C9 C 0.15604(13) -0.01848(16) 0.24802(7) 0.0122(3) Uani 1 1 d . . . . .
H9 H 0.158062 -0.019562 0.294252 0.015 Uiso 1 1 calc R U . . .
C10 C 0.24187(13) 0.06785(16) 0.22054(7) 0.0115(3) Uani 1 1 d . . . . .
C11 C 0.51767(14) 0.31936(17) 0.27438(8) 0.0143(3) Uani 1 1 d . . . . .
H11A H 0.591118 0.321715 0.252115 0.017 Uiso 1 1 calc R U . . .
H11B H 0.488805 0.419979 0.277924 0.017 Uiso 1 1 calc R U . . .
C12 C 0.52395(14) 0.31338(18) 0.39564(8) 0.0161(3) Uani 1 1 d . . . . .
H12 H 0.480100 0.400665 0.399462 0.019 Uiso 1 1 calc R U . . .
C13 C 0.62381(15) 0.10893(18) 0.42018(8) 0.0185(3) Uani 1 1 d . . . . .
H13 H 0.661855 0.029179 0.444463 0.022 Uiso 1 1 calc R U . . .
C14 C 0.61471(15) 0.13041(18) 0.35457(8) 0.0173(3) Uani 1 1 d . . . . .
H14 H 0.645465 0.068596 0.324156 0.021 Uiso 1 1 calc R U . . .
C15 C 0.55173(17) 0.2430(2) 0.51371(8) 0.0258(4) Uani 1 1 d . . . . .
H15A H 0.612213 0.183126 0.541819 0.039 Uiso 1 1 calc R U . . .
H15B H 0.468177 0.213465 0.519023 0.039 Uiso 1 1 calc R U . . .
H15C H 0.564327 0.344726 0.526284 0.039 Uiso 1 1 calc R U . . .
C16 C -0.02323(15) -0.19546(18) 0.23390(8) 0.0170(3) Uani 1 1 d . . . . .
H16A H -0.105497 -0.177769 0.207539 0.020 Uiso 1 1 calc R U . . .
H16B H -0.001616 -0.297865 0.227740 0.020 Uiso 1 1 calc R U . . .
C17 C 0.03396(14) -0.24313(17) 0.35342(8) 0.0158(3) Uani 1 1 d . . . . .
H17 H 0.092753 -0.316952 0.350021 0.019 Uiso 1 1 calc R U . . .
C18 C -0.08440(15) -0.08694(18) 0.39392(9) 0.0191(3) Uani 1 1 d . . . . .
H18 H -0.122457 -0.033139 0.424424 0.023 Uiso 1 1 calc R U . . .
C19 C -0.10535(15) -0.07236(18) 0.32774(8) 0.0175(3) Uani 1 1 d . . . . .
H19 H -0.160867 -0.006633 0.302945 0.021 Uiso 1 1 calc R U . . .
C20 C 0.05539(18) -0.2433(2) 0.47440(9) 0.0259(4) Uani 1 1 d . . . . .
H20A H -0.009020 -0.245587 0.502246 0.039 Uiso 1 1 calc R U . . .
H20B H 0.120990 -0.176692 0.493345 0.039 Uiso 1 1 calc R U . . .
H20C H 0.089823 -0.340400 0.471765 0.039 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
O1 H1A 0.850(2) . ?
O1 H1B 0.850(2) . ?
N1 C12 1.330(2) . ?
N1 C14 1.382(2) . ?
N1 C11 1.460(2) . ?
N2 C12 1.333(2) . ?
N2 C13 1.376(2) . ?
N2 C15 1.466(2) . ?
N3 C17 1.333(2) . ?
N3 C19 1.379(2) . ?
N3 C16 1.462(2) . ?
N4 C17 1.323(2) . ?
N4 C18 1.377(2) . ?
N4 C20 1.457(2) . ?
C1 C2 1.372(2) . ?
C1 C10 1.422(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.417(2) . ?
C2 C11 1.516(2) . ?
C3 C4 1.372(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.418(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.420(2) . ?
C5 C10 1.422(2) . ?
C6 C7 1.367(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.420(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.372(2) . ?
C8 C16 1.510(2) . ?
C9 C10 1.421(2) . ?
C9 H9 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12 0.9500 . ?
C13 C14 1.355(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17 0.9500 . ?
C18 C19 1.354(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
H1A O1 H1B 108.2(6) . . ?
C12 N1 C14 108.53(14) . . ?
C12 N1 C11 126.30(14) . . ?
C14 N1 C11 125.08(13) . . ?
C12 N2 C13 108.91(14) . . ?
C12 N2 C15 125.68(15) . . ?
C13 N2 C15 125.33(15) . . ?
C17 N3 C19 108.70(14) . . ?
C17 N3 C16 125.25(14) . . ?
C19 N3 C16 126.05(14) . . ?
C17 N4 C18 108.81(14) . . ?
C17 N4 C20 125.05(15) . . ?
C18 N4 C20 126.10(15) . . ?
C2 C1 C10 120.63(14) . . ?
C2 C1 H1 119.7 . . ?
C10 C1 H1 119.7 . . ?
C1 C2 C3 120.02(14) . . ?
C1 C2 C11 122.48(14) . . ?
C3 C2 C11 117.50(13) . . ?
C4 C3 C2 120.61(14) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.52(14) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 122.08(14) . . ?
C4 C5 C10 119.05(14) . . ?
C6 C5 C10 118.87(14) . . ?
C7 C6 C5 120.65(14) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.61(14) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 120.02(14) . . ?
C9 C8 C16 123.60(14) . . ?
C7 C8 C16 116.36(13) . . ?
C8 C9 C10 120.53(14) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C5 119.31(14) . . ?
C9 C10 C1 121.57(14) . . ?
C5 C10 C1 119.11(13) . . ?
N1 C11 C2 111.88(12) . . ?
N1 C11 H11A 109.2 . . ?
C2 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C2 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N1 C12 N2 108.52(14) . . ?
N1 C12 H12 125.7 . . ?
N2 C12 H12 125.7 . . ?
C14 C13 N2 106.88(15) . . ?
C14 C13 H13 126.6 . . ?
N2 C13 H13 126.6 . . ?
C13 C14 N1 107.15(14) . . ?
C13 C14 H14 126.4 . . ?
N1 C14 H14 126.4 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C8 113.54(13) . . ?
N3 C16 H16A 108.9 . . ?
C8 C16 H16A 108.9 . . ?
N3 C16 H16B 108.9 . . ?
C8 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
N4 C17 N3 108.59(14) . . ?
N4 C17 H17 125.7 . . ?
N3 C17 H17 125.7 . . ?
C19 C18 N4 107.17(15) . . ?
C19 C18 H18 126.4 . . ?
N4 C18 H18 126.4 . . ?
C18 C19 N3 106.73(14) . . ?
C18 C19 H19 126.6 . . ?
N3 C19 H19 126.6 . . ?
N4 C20 H20A 109.5 . . ?
N4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C10 C1 C2 C3 2.1(2) . . . . ?
C10 C1 C2 C11 -177.77(13) . . . . ?
C1 C2 C3 C4 -1.3(2) . . . . ?
C11 C2 C3 C4 178.55(14) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C3 C4 C5 C6 -177.79(15) . . . . ?
C3 C4 C5 C10 1.9(2) . . . . ?
C4 C5 C6 C7 -179.47(15) . . . . ?
C10 C5 C6 C7 0.8(2) . . . . ?
C5 C6 C7 C8 -0.4(2) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C6 C7 C8 C16 -179.23(15) . . . . ?
C7 C8 C9 C10 0.8(2) . . . . ?
C16 C8 C9 C10 179.54(14) . . . . ?
C8 C9 C10 C5 -0.4(2) . . . . ?
C8 C9 C10 C1 -179.38(14) . . . . ?
C4 C5 C10 C9 179.87(14) . . . . ?
C6 C5 C10 C9 -0.4(2) . . . . ?
C4 C5 C10 C1 -1.1(2) . . . . ?
C6 C5 C10 C1 178.57(14) . . . . ?
C2 C1 C10 C9 178.11(14) . . . . ?
C2 C1 C10 C5 -0.9(2) . . . . ?
C12 N1 C11 C2 -106.29(17) . . . . ?
C14 N1 C11 C2 69.83(19) . . . . ?
C1 C2 C11 N1 27.4(2) . . . . ?
C3 C2 C11 N1 -152.48(13) . . . . ?
C14 N1 C12 N2 0.75(18) . . . . ?
C11 N1 C12 N2 177.40(13) . . . . ?
C13 N2 C12 N1 -0.89(18) . . . . ?
C15 N2 C12 N1 -177.70(15) . . . . ?
C12 N2 C13 C14 0.69(19) . . . . ?
C15 N2 C13 C14 177.51(15) . . . . ?
N2 C13 C14 N1 -0.23(19) . . . . ?
C12 N1 C14 C13 -0.31(18) . . . . ?
C11 N1 C14 C13 -177.02(14) . . . . ?
C17 N3 C16 C8 -91.89(18) . . . . ?
C19 N3 C16 C8 88.71(19) . . . . ?
C9 C8 C16 N3 11.4(2) . . . . ?
C7 C8 C16 N3 -169.87(14) . . . . ?
C18 N4 C17 N3 -0.51(18) . . . . ?
C20 N4 C17 N3 -178.20(15) . . . . ?
C19 N3 C17 N4 0.45(18) . . . . ?
C16 N3 C17 N4 -179.04(14) . . . . ?
C17 N4 C18 C19 0.37(19) . . . . ?
C20 N4 C18 C19 178.03(16) . . . . ?
N4 C18 C19 N3 -0.09(19) . . . . ?
C17 N3 C19 C18 -0.21(18) . . . . ?
C16 N3 C19 C18 179.27(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A Br1 0.850(2) 2.476(6) 3.3159(15) 170(2) . yes
O1 H1B Br2 0.850(2) 2.455(3) 3.3041(14) 178(2) . yes
C11 H11A Br2 0.99 3.05 3.7541(16) 129.2 2_645 yes
C11 H11B Br2 0.99 2.82 3.6446(16) 140.8 . yes
C12 H12 Br2 0.95 2.97 3.7241(16) 137.4 . yes
C13 H13 Br1 0.95 2.79 3.6656(17) 153.0 3_656 yes
C14 H14 Br2 0.95 3.07 3.8438(17) 139.5 2_645 yes
C15 H15B Br1 0.98 3.09 3.9105(19) 141.9 . yes
C15 H15C O1 0.98 2.67 3.472(3) 138.9 3_666 yes
C16 H16A Br2 0.99 3.11 3.8884(18) 136.7 2_545 yes
C17 H17 Br2 0.95 2.59 3.4713(16) 154.6 1_545 yes
C19 H19 Br2 0.95 2.74 3.5898(17) 149.3 2_545 yes
C20 H20A Br1 0.98 3.08 3.974(2) 151.6 3_556 yes
C20 H20B Br1 0.98 3.09 3.814(2) 132.0 . yes

_refine_diff_density_max         0.532
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.087



