# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A
_database_code_depnum_ccdc_archive 'CCDC 1961317'
loop_
_audit_author_name
_audit_author_address
'Edward Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2019-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 Cl N5 O, C2 H6 O'
_chemical_formula_sum            'C18 H22 Cl N5 O2'
_chemical_formula_weight         375.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   13.2045(2)
_cell_length_b                   9.7903(2)
_cell_length_c                   14.8676(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.816(2)
_cell_angle_gamma                90
_cell_volume                     1917.76(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    15688
_cell_measurement_theta_min      3.3760
_cell_measurement_theta_max      76.4060

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.043
_exptl_absorpt_coefficient_mu    1.949
_shelx_estimated_absorpt_T_min   0.793
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.746
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_reflns_number            24367
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.979
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_full        67.070
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             6693
_reflns_number_gt                6456
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_max     0.947
_reflns_Friedel_fraction_full    0.947

_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 1.171.39.31a (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0705P)²+3.0360P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2772 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6693
_refine_ls_number_parameters     503
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1457
_refine_ls_wR_factor_gt          0.1445
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.007
_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
Cl1 Cl 0.12090(10) 0.16254(16) 0.25284(9) 0.0333(3) Uani 1 1 d . . . . .
Cl2 Cl 0.87439(11) 0.20531(18) -0.21996(9) 0.0380(4) Uani 1 1 d . . . . .
O1 O 0.0330(3) 0.5191(5) 0.9030(3) 0.0342(10) Uani 1 1 d . . . . .
O2 O 1.0002(3) 0.5407(5) 0.4273(3) 0.0353(10) Uani 1 1 d . . . . .
O3 O 0.3966(3) 0.6826(4) 0.4408(2) 0.0206(7) Uani 1 1 d D . . . .
H3O H 0.383(4) 0.625(5) 0.484(3) 0.025 Uiso 1 1 d D U . . .
O4 O 0.6001(3) 0.6919(4) 0.9532(2) 0.0184(7) Uani 1 1 d D . . . .
H4O H 0.620(4) 0.643(6) 1.000(3) 0.022 Uiso 1 1 d D U . . .
N1 N 0.3576(3) 0.5537(4) 0.5962(2) 0.0158(8) Uani 1 1 d . . . . .
N2 N 0.4712(3) 0.4082(4) 0.6857(3) 0.0150(8) Uani 1 1 d . . . . .
N3 N 0.4442(3) 0.6328(4) 0.7332(3) 0.0154(8) Uani 1 1 d D . . . .
H3N H 0.460(4) 0.706(4) 0.766(3) 0.019 Uiso 1 1 d D U . . .
N4 N 0.5570(3) 0.4913(5) 0.8139(3) 0.0201(9) Uani 1 1 d D . . . .
H4NA H 0.590(4) 0.413(3) 0.815(4) 0.024 Uiso 1 1 d D U . . .
H4NB H 0.562(4) 0.551(5) 0.858(3) 0.024 Uiso 1 1 d D U . . .
N5 N 0.4200(3) 0.3490(4) 0.5419(3) 0.0162(8) Uani 1 1 d D . . . .
H5N H 0.469(3) 0.289(5) 0.551(4) 0.019 Uiso 1 1 d D U . . .
N6 N 0.6408(3) 0.5603(4) 0.1136(3) 0.0166(8) Uani 1 1 d . . . . .
N7 N 0.5333(3) 0.4082(4) 0.1907(3) 0.0178(9) Uani 1 1 d . . . . .
N8 N 0.5516(3) 0.6336(4) 0.2401(3) 0.0159(8) Uani 1 1 d D . . . .
H8N H 0.531(4) 0.709(3) 0.265(4) 0.019 Uiso 1 1 d D U . . .
N9 N 0.4390(4) 0.4877(5) 0.3049(3) 0.0216(9) Uani 1 1 d D . . . .
H9NA H 0.416(4) 0.403(3) 0.305(4) 0.026 Uiso 1 1 d D U . . .
H9NB H 0.444(5) 0.546(5) 0.350(3) 0.026 Uiso 1 1 d D U . . .
N10 N 0.5867(3) 0.3507(4) 0.0533(3) 0.0177(8) Uani 1 1 d D . . . .
H10N H 0.539(3) 0.289(5) 0.056(4) 0.021 Uiso 1 1 d D U . . .
C1 C 0.3502(4) 0.6399(5) 0.6746(3) 0.0166(9) Uani 1 1 d . . . . .
H1 H 0.342640 0.736228 0.652771 0.020 Uiso 1 1 calc R U . . .
C2 C 0.4125(4) 0.4438(5) 0.6096(3) 0.0136(9) Uani 1 1 d . . . . .
C3 C 0.4890(4) 0.5111(5) 0.7439(3) 0.0147(9) Uani 1 1 d . . . . .
C4 C 0.2591(4) 0.6079(5) 0.7291(3) 0.0168(10) Uani 1 1 d . . . . .
C5 C 0.2276(4) 0.7078(6) 0.7878(4) 0.0291(12) Uani 1 1 d . . . . .
H5 H 0.258717 0.795304 0.787842 0.035 Uiso 1 1 calc R U . . .
C6 C 0.1521(4) 0.6832(7) 0.8460(4) 0.0331(14) Uani 1 1 d . . . . .
H6 H 0.131942 0.753160 0.885328 0.040 Uiso 1 1 calc R U . . .
C7 C 0.1064(4) 0.5566(7) 0.8468(3) 0.0258(12) Uani 1 1 d . . . . .
C8 C 0.1341(4) 0.4567(6) 0.7856(4) 0.0249(11) Uani 1 1 d . . . . .
H8 H 0.100570 0.370740 0.783649 0.030 Uiso 1 1 calc R U . . .
C9 C 0.2097(4) 0.4821(5) 0.7279(3) 0.0211(10) Uani 1 1 d . . . . .
H9 H 0.228251 0.413243 0.687142 0.025 Uiso 1 1 calc R U . . .
C10 C 0.0117(5) 0.6137(10) 0.9722(4) 0.050(2) Uani 1 1 d . . . . .
H10A H -0.016974 0.697479 0.944823 0.075 Uiso 1 1 calc R U . . .
H10B H 0.074534 0.635570 1.008097 0.075 Uiso 1 1 calc R U . . .
H10C H -0.037209 0.573214 1.011220 0.075 Uiso 1 1 calc R U . . .
C11 C 0.3485(4) 0.3154(5) 0.4718(3) 0.0159(10) Uani 1 1 d . . . . .
C12 C 0.3701(4) 0.2003(5) 0.4196(3) 0.0189(10) Uani 1 1 d . . . . .
H12 H 0.432450 0.153006 0.431238 0.023 Uiso 1 1 calc R U . . .
C13 C 0.3010(4) 0.1553(6) 0.3511(3) 0.0211(10) Uani 1 1 d . . . . .
H13 H 0.316013 0.077459 0.316243 0.025 Uiso 1 1 calc R U . . .
C14 C 0.2102(4) 0.2244(6) 0.3342(3) 0.0218(11) Uani 1 1 d . . . . .
C15 C 0.1886(4) 0.3388(6) 0.3839(3) 0.0207(11) Uani 1 1 d . . . . .
H15 H 0.126261 0.385754 0.371511 0.025 Uiso 1 1 calc R U . . .
C16 C 0.2576(4) 0.3859(5) 0.4522(3) 0.0186(10) Uani 1 1 d . . . . .
H16 H 0.242766 0.465699 0.485293 0.022 Uiso 1 1 calc R U . . .
C17 C 0.6462(4) 0.6437(5) 0.1961(3) 0.0171(10) Uani 1 1 d . . . . .
H17 H 0.654225 0.741075 0.177465 0.021 Uiso 1 1 calc R U . . .
C18 C 0.5903(4) 0.4460(5) 0.1215(3) 0.0140(9) Uani 1 1 d . . . . .
C19 C 0.5090(4) 0.5098(5) 0.2457(3) 0.0163(10) Uani 1 1 d . . . . .
C20 C 0.7383(4) 0.6071(5) 0.2589(3) 0.0184(10) Uani 1 1 d . . . . .
C21 C 0.7365(4) 0.6254(6) 0.3515(3) 0.0235(11) Uani 1 1 d . . . . .
H21 H 0.674988 0.653306 0.375679 0.028 Uiso 1 1 calc R U . . .
C22 C 0.8217(4) 0.6042(6) 0.4100(4) 0.0280(12) Uani 1 1 d . . . . .
H22 H 0.818276 0.618973 0.472864 0.034 Uiso 1 1 calc R U . . .
C23 C 0.9111(4) 0.5618(6) 0.3763(4) 0.0233(11) Uani 1 1 d . . . . .
C24 C 0.9139(4) 0.5402(6) 0.2832(4) 0.0267(12) Uani 1 1 d . . . . .
H24 H 0.974718 0.508997 0.259257 0.032 Uiso 1 1 calc R U . . .
C25 C 0.8295(4) 0.5636(6) 0.2266(4) 0.0244(11) Uani 1 1 d . . . . .
H25 H 0.833377 0.549925 0.163613 0.029 Uiso 1 1 calc R U . . .
C26 C 1.0033(5) 0.5758(9) 0.5212(4) 0.0408(16) Uani 1 1 d . . . . .
H26A H 0.985723 0.672363 0.527593 0.061 Uiso 1 1 calc R U . . .
H26B H 1.071735 0.559558 0.548761 0.061 Uiso 1 1 calc R U . . .
H26C H 0.954512 0.519259 0.551377 0.061 Uiso 1 1 calc R U . . .
C27 C 0.6559(4) 0.3247(5) -0.0120(3) 0.0162(10) Uani 1 1 d . . . . .
C28 C 0.7397(4) 0.4049(5) -0.0262(3) 0.0190(10) Uani 1 1 d . . . . .
H28 H 0.751924 0.485274 0.008586 0.023 Uiso 1 1 calc R U . . .
C29 C 0.8063(4) 0.3688(6) -0.0911(3) 0.0215(10) Uani 1 1 d . . . . .
H29 H 0.863943 0.423953 -0.100000 0.026 Uiso 1 1 calc R U . . .
C30 C 0.7883(4) 0.2529(6) -0.1424(3) 0.0237(11) Uani 1 1 d . . . . .
C31 C 0.7039(4) 0.1714(6) -0.1301(3) 0.0237(11) Uani 1 1 d . . . . .
H31 H 0.691571 0.091904 -0.165808 0.028 Uiso 1 1 calc R U . . .
C32 C 0.6380(4) 0.2072(6) -0.0653(3) 0.0198(10) Uani 1 1 d . . . . .
H32 H 0.580180 0.152081 -0.056789 0.024 Uiso 1 1 calc R U . . .
C33 C 0.3118(5) 0.7496(10) 0.4012(5) 0.058(2) Uani 1 1 d . . . . .
H33A H 0.271525 0.681704 0.364687 0.070 Uiso 1 1 calc R U . . .
H33B H 0.336171 0.818297 0.358800 0.070 Uiso 1 1 calc R U . . .
C34 C 0.2451(9) 0.8166(13) 0.4573(6) 0.084(4) Uani 1 1 d . . . . .
H34A H 0.191149 0.861968 0.419934 0.127 Uiso 1 1 calc R U . . .
H34B H 0.282877 0.884748 0.494303 0.127 Uiso 1 1 calc R U . . .
H34C H 0.215016 0.749509 0.496543 0.127 Uiso 1 1 calc R U . . .
C35 C 0.6867(4) 0.7638(6) 0.9225(4) 0.0271(12) Uani 1 1 d . . . . .
H35A H 0.663665 0.826945 0.873343 0.032 Uiso 1 1 calc R U . . .
H35B H 0.733857 0.697142 0.897754 0.032 Uiso 1 1 calc R U . . .
C36 C 0.7424(5) 0.8439(7) 0.9968(4) 0.0394(15) Uani 1 1 d . . . . .
H36A H 0.800453 0.890820 0.972891 0.059 Uiso 1 1 calc R U . . .
H36B H 0.766630 0.781660 1.045194 0.059 Uiso 1 1 calc R U . . .
H36C H 0.696497 0.911506 1.020729 0.059 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
Cl1 C14 1.741(5) . ?
Cl2 C30 1.736(5) . ?
O1 C7 1.370(7) . ?
O1 C10 1.427(8) . ?
O2 C23 1.372(6) . ?
O2 C26 1.436(7) . ?
O3 C33 1.394(8) . ?
O3 H3O 0.882(14) . ?
O4 C35 1.442(6) . ?
O4 H4O 0.874(14) . ?
N1 C2 1.305(6) . ?
N1 C1 1.447(6) . ?
N2 C3 1.339(6) . ?
N2 C2 1.373(6) . ?
N3 C3 1.334(6) . ?
N3 C1 1.470(6) . ?
N3 H3N 0.883(14) . ?
N4 C3 1.343(6) . ?
N4 H4NA 0.878(14) . ?
N4 H4NB 0.881(14) . ?
N5 C2 1.378(6) . ?
N5 C11 1.398(6) . ?
N5 H5N 0.874(14) . ?
N6 C18 1.312(7) . ?
N6 C17 1.471(6) . ?
N7 C19 1.340(6) . ?
N7 C18 1.366(6) . ?
N8 C19 1.342(7) . ?
N8 C17 1.452(6) . ?
N8 H8N 0.877(14) . ?
N9 C19 1.335(7) . ?
N9 H9NA 0.882(14) . ?
N9 H9NB 0.880(14) . ?
N10 C18 1.376(6) . ?
N10 C27 1.400(6) . ?
N10 H10N 0.878(14) . ?
C1 C4 1.528(7) . ?
C1 H1 1.0000 . ?
C4 C9 1.393(7) . ?
C4 C5 1.392(7) . ?
C5 C6 1.384(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.380(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.401(8) . ?
C8 C9 1.381(8) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.399(7) . ?
C11 C12 1.408(7) . ?
C12 C13 1.394(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(8) . ?
C15 C16 1.397(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C20 1.526(7) . ?
C17 H17 1.0000 . ?
C20 C21 1.390(7) . ?
C20 C25 1.394(7) . ?
C21 C22 1.391(8) . ?
C21 H21 0.9500 . ?
C22 C23 1.376(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.404(8) . ?
C24 C25 1.370(8) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.384(7) . ?
C27 C32 1.408(7) . ?
C28 C29 1.393(7) . ?
C28 H28 0.9500 . ?
C29 C30 1.379(8) . ?
C29 H29 0.9500 . ?
C30 C31 1.393(8) . ?
C31 C32 1.385(7) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.414(12) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.507(9) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 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
C7 O1 C10 116.6(5) . . ?
C23 O2 C26 117.9(4) . . ?
C33 O3 H3O 114(4) . . ?
C35 O4 H4O 108(4) . . ?
C2 N1 C1 115.1(4) . . ?
C3 N2 C2 114.0(4) . . ?
C3 N3 C1 117.6(4) . . ?
C3 N3 H3N 125(4) . . ?
C1 N3 H3N 116(4) . . ?
C3 N4 H4NA 116(4) . . ?
C3 N4 H4NB 120(4) . . ?
H4NA N4 H4NB 123(6) . . ?
C2 N5 C11 128.7(4) . . ?
C2 N5 H5N 115(4) . . ?
C11 N5 H5N 115(4) . . ?
C18 N6 C17 113.3(4) . . ?
C19 N7 C18 115.1(4) . . ?
C19 N8 C17 117.8(4) . . ?
C19 N8 H8N 127(4) . . ?
C17 N8 H8N 115(4) . . ?
C19 N9 H9NA 114(4) . . ?
C19 N9 H9NB 113(4) . . ?
H9NA N9 H9NB 127(6) . . ?
C18 N10 C27 129.9(4) . . ?
C18 N10 H10N 115(4) . . ?
C27 N10 H10N 114(4) . . ?
N1 C1 N3 110.5(4) . . ?
N1 C1 C4 113.9(4) . . ?
N3 C1 C4 109.8(4) . . ?
N1 C1 H1 107.4 . . ?
N3 C1 H1 107.4 . . ?
C4 C1 H1 107.4 . . ?
N1 C2 N2 127.8(4) . . ?
N1 C2 N5 120.6(4) . . ?
N2 C2 N5 111.5(4) . . ?
N3 C3 N2 122.5(4) . . ?
N3 C3 N4 119.3(4) . . ?
N2 C3 N4 118.1(4) . . ?
C9 C4 C5 118.0(5) . . ?
C9 C4 C1 124.0(4) . . ?
C5 C4 C1 117.9(5) . . ?
C6 C5 C4 121.8(5) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C7 C6 C5 119.7(5) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
O1 C7 C6 125.0(5) . . ?
O1 C7 C8 115.8(5) . . ?
C6 C7 C8 119.2(5) . . ?
C9 C8 C7 120.5(5) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C4 120.6(5) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N5 C11 C16 124.5(4) . . ?
N5 C11 C12 116.6(4) . . ?
C16 C11 C12 118.9(5) . . ?
C13 C12 C11 120.6(5) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 119.7(5) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 120.4(5) . . ?
C15 C14 Cl1 120.0(4) . . ?
C13 C14 Cl1 119.6(4) . . ?
C14 C15 C16 120.6(5) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 119.8(5) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
N8 C17 N6 110.0(4) . . ?
N8 C17 C20 112.5(4) . . ?
N6 C17 C20 111.9(4) . . ?
N8 C17 H17 107.4 . . ?
N6 C17 H17 107.4 . . ?
C20 C17 H17 107.4 . . ?
N6 C18 N7 127.4(4) . . ?
N6 C18 N10 120.3(4) . . ?
N7 C18 N10 112.2(4) . . ?
N9 C19 N7 119.1(5) . . ?
N9 C19 N8 119.9(4) . . ?
N7 C19 N8 121.0(4) . . ?
C21 C20 C25 117.0(5) . . ?
C21 C20 C17 120.7(4) . . ?
C25 C20 C17 122.1(4) . . ?
C20 C21 C22 122.2(5) . . ?
C20 C21 H21 118.9 . . ?
C22 C21 H21 118.9 . . ?
C23 C22 C21 119.7(5) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
O2 C23 C22 124.7(5) . . ?
O2 C23 C24 116.4(5) . . ?
C22 C23 C24 118.9(5) . . ?
C25 C24 C23 120.5(5) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C20 121.7(5) . . ?
C24 C25 H25 119.2 . . ?
C20 C25 H25 119.2 . . ?
O2 C26 H26A 109.5 . . ?
O2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 N10 124.6(5) . . ?
C28 C27 C32 118.9(5) . . ?
N10 C27 C32 116.4(4) . . ?
C27 C28 C29 120.6(5) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C30 C29 C28 119.9(5) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C29 C30 C31 120.6(5) . . ?
C29 C30 Cl2 119.5(4) . . ?
C31 C30 Cl2 119.9(4) . . ?
C32 C31 C30 119.4(5) . . ?
C32 C31 H31 120.3 . . ?
C30 C31 H31 120.3 . . ?
C31 C32 C27 120.5(5) . . ?
C31 C32 H32 119.7 . . ?
C27 C32 H32 119.7 . . ?
O3 C33 C34 118.9(7) . . ?
O3 C33 H33A 107.6 . . ?
C34 C33 H33A 107.6 . . ?
O3 C33 H33B 107.6 . . ?
C34 C33 H33B 107.6 . . ?
H33A C33 H33B 107.0 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O4 C35 C36 112.5(5) . . ?
O4 C35 H35A 109.1 . . ?
C36 C35 H35A 109.1 . . ?
O4 C35 H35B 109.1 . . ?
C36 C35 H35B 109.1 . . ?
H35A C35 H35B 107.8 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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
C2 N1 C1 N3 32.3(6) . . . . ?
C2 N1 C1 C4 -91.9(5) . . . . ?
C3 N3 C1 N1 -39.6(6) . . . . ?
C3 N3 C1 C4 86.9(5) . . . . ?
C1 N1 C2 N2 -7.1(7) . . . . ?
C1 N1 C2 N5 175.8(4) . . . . ?
C3 N2 C2 N1 -14.5(7) . . . . ?
C3 N2 C2 N5 162.9(4) . . . . ?
C11 N5 C2 N1 -30.4(7) . . . . ?
C11 N5 C2 N2 152.1(5) . . . . ?
C1 N3 C3 N2 20.3(7) . . . . ?
C1 N3 C3 N4 -161.9(4) . . . . ?
C2 N2 C3 N3 7.0(7) . . . . ?
C2 N2 C3 N4 -170.9(4) . . . . ?
N1 C1 C4 C9 23.4(6) . . . . ?
N3 C1 C4 C9 -101.2(5) . . . . ?
N1 C1 C4 C5 -160.8(4) . . . . ?
N3 C1 C4 C5 74.6(6) . . . . ?
C9 C4 C5 C6 2.3(8) . . . . ?
C1 C4 C5 C6 -173.7(5) . . . . ?
C4 C5 C6 C7 0.1(9) . . . . ?
C10 O1 C7 C6 -7.5(8) . . . . ?
C10 O1 C7 C8 173.4(5) . . . . ?
C5 C6 C7 O1 178.1(5) . . . . ?
C5 C6 C7 C8 -2.8(9) . . . . ?
O1 C7 C8 C9 -177.8(5) . . . . ?
C6 C7 C8 C9 3.1(8) . . . . ?
C7 C8 C9 C4 -0.6(8) . . . . ?
C5 C4 C9 C8 -2.0(7) . . . . ?
C1 C4 C9 C8 173.7(5) . . . . ?
C2 N5 C11 C16 7.6(8) . . . . ?
C2 N5 C11 C12 -170.8(4) . . . . ?
N5 C11 C12 C13 176.9(4) . . . . ?
C16 C11 C12 C13 -1.6(7) . . . . ?
C11 C12 C13 C14 0.1(8) . . . . ?
C12 C13 C14 C15 0.9(8) . . . . ?
C12 C13 C14 Cl1 -176.5(4) . . . . ?
C13 C14 C15 C16 -0.3(8) . . . . ?
Cl1 C14 C15 C16 177.1(4) . . . . ?
C14 C15 C16 C11 -1.3(8) . . . . ?
N5 C11 C16 C15 -176.2(5) . . . . ?
C12 C11 C16 C15 2.2(7) . . . . ?
C19 N8 C17 N6 43.0(6) . . . . ?
C19 N8 C17 C20 -82.4(5) . . . . ?
C18 N6 C17 N8 -36.7(5) . . . . ?
C18 N6 C17 C20 89.1(5) . . . . ?
C17 N6 C18 N7 9.6(7) . . . . ?
C17 N6 C18 N10 -173.7(4) . . . . ?
C19 N7 C18 N6 15.6(7) . . . . ?
C19 N7 C18 N10 -161.4(4) . . . . ?
C27 N10 C18 N6 26.8(8) . . . . ?
C27 N10 C18 N7 -156.0(5) . . . . ?
C18 N7 C19 N9 168.1(4) . . . . ?
C18 N7 C19 N8 -10.0(7) . . . . ?
C17 N8 C19 N9 162.0(4) . . . . ?
C17 N8 C19 N7 -19.9(7) . . . . ?
N8 C17 C20 C21 -27.5(6) . . . . ?
N6 C17 C20 C21 -151.9(5) . . . . ?
N8 C17 C20 C25 157.2(5) . . . . ?
N6 C17 C20 C25 32.8(6) . . . . ?
C25 C20 C21 C22 1.2(8) . . . . ?
C17 C20 C21 C22 -174.4(5) . . . . ?
C20 C21 C22 C23 -0.9(9) . . . . ?
C26 O2 C23 C22 -5.4(9) . . . . ?
C26 O2 C23 C24 173.5(6) . . . . ?
C21 C22 C23 O2 178.5(6) . . . . ?
C21 C22 C23 C24 -0.3(9) . . . . ?
O2 C23 C24 C25 -177.6(5) . . . . ?
C22 C23 C24 C25 1.4(9) . . . . ?
C23 C24 C25 C20 -1.1(9) . . . . ?
C21 C20 C25 C24 -0.1(8) . . . . ?
C17 C20 C25 C24 175.3(5) . . . . ?
C18 N10 C27 C28 -7.8(8) . . . . ?
C18 N10 C27 C32 171.4(5) . . . . ?
N10 C27 C28 C29 178.1(5) . . . . ?
C32 C27 C28 C29 -1.1(7) . . . . ?
C27 C28 C29 C30 0.6(8) . . . . ?
C28 C29 C30 C31 0.1(8) . . . . ?
C28 C29 C30 Cl2 -177.5(4) . . . . ?
C29 C30 C31 C32 -0.4(8) . . . . ?
Cl2 C30 C31 C32 177.3(4) . . . . ?
C30 C31 C32 C27 -0.2(8) . . . . ?
C28 C27 C32 C31 0.9(7) . . . . ?
N10 C27 C32 C31 -178.3(4) . . . . ?

_refine_diff_density_max         0.597
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_A_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1961319'
loop_
_audit_author_name
_audit_author_address
'Edward Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2019-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 Br N5, C2 H6 O'
_chemical_formula_sum            'C17 H20 Br N5 O'
_chemical_formula_weight         390.29

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   12.7568(4)
_cell_length_b                   9.7768(3)
_cell_length_c                   15.1645(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.622(3)
_cell_angle_gamma                90
_cell_volume                     1781.49(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9148
_cell_measurement_theta_min      3.0640
_cell_measurement_theta_max      76.2950

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.111
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.019
_exptl_absorpt_coefficient_mu    3.258
_shelx_estimated_absorpt_T_min   0.714
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_reflns_number            22035
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.094
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_full        67.078
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.926
_reflns_number_total             5907
_reflns_number_gt                5554
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_max     0.842
_reflns_Friedel_fraction_full    0.842

_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 1.171.39.31a (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0580P)²+0.0193P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2170 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(15)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5907
_refine_ls_number_parameters     465
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.024
_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 0.10014(4) 0.80935(6) 0.13714(3) 0.03102(16) Uani 1 1 d . . . . .
Br2 Br 0.93638(4) 0.79266(8) -0.11941(3) 0.03927(19) Uani 1 1 d . . . . .
O1 O 0.3879(3) 0.3504(3) 0.4112(2) 0.0193(7) Uani 1 1 d D . . . .
H1O H 0.377(5) 0.391(6) 0.456(3) 0.023 Uiso 1 1 d D U . . .
O2 O 0.6032(3) 0.3337(4) -0.0222(2) 0.0240(8) Uani 1 1 d D . . . .
H2O H 0.620(5) 0.377(6) 0.028(3) 0.029 Uiso 1 1 d D U . . .
N1 N 0.3590(4) 0.4682(4) 0.5645(3) 0.0189(8) Uani 1 1 d . . . . .
N2 N 0.4755(3) 0.6181(4) 0.6834(3) 0.0182(8) Uani 1 1 d . . . . .
N3 N 0.4508(4) 0.3911(4) 0.7220(3) 0.0180(8) Uani 1 1 d D . . . .
H3N H 0.458(4) 0.315(3) 0.755(3) 0.022 Uiso 1 1 d D U . . .
N4 N 0.5688(4) 0.5340(5) 0.8311(3) 0.0237(9) Uani 1 1 d D . . . .
H4NA H 0.603(5) 0.614(3) 0.844(4) 0.028 Uiso 1 1 d D U . . .
H4NB H 0.573(5) 0.471(5) 0.873(3) 0.028 Uiso 1 1 d D U . . .
N5 N 0.4133(3) 0.6840(4) 0.5304(3) 0.0182(8) Uani 1 1 d D . . . .
H5N H 0.470(3) 0.741(5) 0.550(4) 0.022 Uiso 1 1 d D U . . .
N6 N 0.6468(4) 0.4609(4) 0.1449(3) 0.0189(8) Uani 1 1 d . . . . .
N7 N 0.5355(4) 0.6193(4) 0.1965(3) 0.0201(9) Uani 1 1 d . . . . .
N8 N 0.5508(4) 0.3944(4) 0.2499(3) 0.0200(9) Uani 1 1 d D . . . .
H8N H 0.529(4) 0.320(4) 0.271(4) 0.024 Uiso 1 1 d D U . . .
N9 N 0.4305(4) 0.5439(5) 0.2843(3) 0.0238(9) Uani 1 1 d D . . . .
H9NA H 0.408(5) 0.629(3) 0.279(4) 0.029 Uiso 1 1 d D U . . .
H9NB H 0.419(5) 0.487(5) 0.325(3) 0.029 Uiso 1 1 d D U . . .
N10 N 0.6013(4) 0.6774(4) 0.0784(3) 0.0209(9) Uani 1 1 d D . . . .
H10N H 0.544(3) 0.733(5) 0.066(4) 0.025 Uiso 1 1 d D U . . .
C1 C 0.3518(4) 0.3768(5) 0.6374(3) 0.0187(10) Uani 1 1 d . . . . .
H1 H 0.350632 0.280998 0.614030 0.022 Uiso 1 1 calc R U . . .
C2 C 0.4124(4) 0.5820(5) 0.5932(3) 0.0163(9) Uani 1 1 d . . . . .
C3 C 0.4953(4) 0.5142(5) 0.7442(3) 0.0183(10) Uani 1 1 d . . . . .
C4 C 0.2455(4) 0.3985(5) 0.6614(3) 0.0208(10) Uani 1 1 d . . . . .
C5 C 0.1985(5) 0.2879(7) 0.6912(4) 0.0367(13) Uani 1 1 d . . . . .
H5 H 0.228351 0.198829 0.691324 0.044 Uiso 1 1 calc R U . . .
C6 C 0.1076(5) 0.3071(8) 0.7210(5) 0.0462(16) Uani 1 1 d . . . . .
H6 H 0.077396 0.231282 0.743422 0.055 Uiso 1 1 calc R U . . .
C7 C 0.0619(5) 0.4321(8) 0.7184(4) 0.0382(15) Uani 1 1 d . . . . .
H7 H -0.001286 0.443313 0.737473 0.046 Uiso 1 1 calc R U . . .
C8 C 0.1065(5) 0.5430(7) 0.6883(4) 0.0347(13) Uani 1 1 d . . . . .
H8 H 0.073920 0.630855 0.686228 0.042 Uiso 1 1 calc R U . . .
C9 C 0.2005(5) 0.5264(6) 0.6606(4) 0.0297(12) Uani 1 1 d . . . . .
H9 H 0.232842 0.603418 0.641360 0.036 Uiso 1 1 calc R U . . .
C10 C 0.3372(4) 0.7080(5) 0.4410(3) 0.0173(10) Uani 1 1 d . . . . .
C11 C 0.3588(4) 0.8191(6) 0.3912(3) 0.0199(9) Uani 1 1 d . . . . .
H11 H 0.423220 0.873360 0.419023 0.024 Uiso 1 1 calc R U . . .
C12 C 0.2879(4) 0.8511(5) 0.3020(3) 0.0238(11) Uani 1 1 d . . . . .
H12 H 0.302967 0.927490 0.269423 0.029 Uiso 1 1 calc R U . . .
C13 C 0.1953(4) 0.7710(6) 0.2613(3) 0.0243(11) Uani 1 1 d . . . . .
C14 C 0.1705(4) 0.6643(5) 0.3089(3) 0.0224(10) Uani 1 1 d . . . . .
H14 H 0.105365 0.611462 0.280233 0.027 Uiso 1 1 calc R U . . .
C15 C 0.2396(4) 0.6324(5) 0.3986(3) 0.0209(10) Uani 1 1 d . . . . .
H15 H 0.220837 0.559118 0.431674 0.025 Uiso 1 1 calc R U . . .
C16 C 0.6498(4) 0.3746(5) 0.2245(3) 0.0192(10) Uani 1 1 d . . . . .
H16 H 0.649659 0.277270 0.204178 0.023 Uiso 1 1 calc R U . . .
C17 C 0.5986(4) 0.5784(5) 0.1424(3) 0.0175(10) Uani 1 1 d . . . . .
C18 C 0.5083(4) 0.5203(5) 0.2438(3) 0.0194(11) Uani 1 1 d . . . . .
C19 C 0.7592(4) 0.3982(5) 0.3064(3) 0.0210(10) Uani 1 1 d . . . . .
C20 C 0.8589(5) 0.4037(6) 0.2888(4) 0.0267(11) Uani 1 1 d . . . . .
H20 H 0.858436 0.399439 0.226104 0.032 Uiso 1 1 calc R U . . .
C21 C 0.9595(5) 0.4152(7) 0.3615(4) 0.0359(13) Uani 1 1 d . . . . .
H21 H 1.027372 0.419036 0.348655 0.043 Uiso 1 1 calc R U . . .
C22 C 0.9604(5) 0.4211(7) 0.4531(4) 0.0419(15) Uani 1 1 d . . . . .
H22 H 1.029085 0.428209 0.503190 0.050 Uiso 1 1 calc R U . . .
C23 C 0.8626(5) 0.4169(7) 0.4715(4) 0.0381(14) Uani 1 1 d . . . . .
H23 H 0.863726 0.421783 0.534428 0.046 Uiso 1 1 calc R U . . .
C24 C 0.7606(5) 0.4053(6) 0.3984(4) 0.0277(11) Uani 1 1 d . . . . .
H24 H 0.692863 0.402309 0.411586 0.033 Uiso 1 1 calc R U . . .
C25 C 0.6794(4) 0.6944(5) 0.0324(3) 0.0208(10) Uani 1 1 d . . . . .
C26 C 0.7728(4) 0.6133(6) 0.0470(3) 0.0229(10) Uani 1 1 d . . . . .
H26 H 0.785890 0.538111 0.089014 0.027 Uiso 1 1 calc R U . . .
C27 C 0.8479(5) 0.6416(6) 0.0001(3) 0.0256(11) Uani 1 1 d . . . . .
H27 H 0.911740 0.585694 0.010020 0.031 Uiso 1 1 calc R U . . .
C28 C 0.8286(4) 0.7516(6) -0.0608(3) 0.0254(11) Uani 1 1 d . . . . .
C29 C 0.7358(5) 0.8320(5) -0.0769(3) 0.0266(12) Uani 1 1 d . . . . .
H29 H 0.723078 0.906502 -0.119438 0.032 Uiso 1 1 calc R U . . .
C30 C 0.6606(4) 0.8044(6) -0.0311(3) 0.0229(9) Uani 1 1 d . . . . .
H30 H 0.596200 0.859780 -0.042545 0.027 Uiso 1 1 calc R U . . .
C31 C 0.2900(4) 0.2816(6) 0.3525(3) 0.0255(11) Uani 1 1 d . . . . .
H31A H 0.309098 0.228680 0.304255 0.031 Uiso 1 1 calc R U . . .
H31B H 0.233614 0.350675 0.319842 0.031 Uiso 1 1 calc R U . . .
C32 C 0.2406(6) 0.1864(7) 0.4058(4) 0.0368(14) Uani 1 1 d . . . . .
H32A H 0.176295 0.139283 0.362042 0.055 Uiso 1 1 calc R U . . .
H32B H 0.216837 0.238988 0.450779 0.055 Uiso 1 1 calc R U . . .
H32C H 0.296546 0.118841 0.439420 0.055 Uiso 1 1 calc R U . . .
C33 C 0.6956(5) 0.2490(7) -0.0201(4) 0.0344(13) Uani 1 1 d . . . . .
H33A H 0.760917 0.307883 -0.013381 0.041 Uiso 1 1 calc R U . . .
H33B H 0.677371 0.199961 -0.080553 0.041 Uiso 1 1 calc R U . . .
C34 C 0.7254(7) 0.1470(8) 0.0574(5) 0.0481(17) Uani 1 1 d . . . . .
H34A H 0.785391 0.088036 0.052521 0.072 Uiso 1 1 calc R U . . .
H34B H 0.660124 0.090949 0.052926 0.072 Uiso 1 1 calc R U . . .
H34C H 0.750382 0.194789 0.117667 0.072 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 C13 1.904(5) . ?
Br2 C28 1.914(5) . ?
O1 C31 1.435(6) . ?
O1 H1O 0.838(14) . ?
O2 C33 1.432(7) . ?
O2 H2O 0.840(14) . ?
N1 C2 1.301(7) . ?
N1 C1 1.448(6) . ?
N2 C3 1.338(6) . ?
N2 C2 1.379(6) . ?
N3 C3 1.324(7) . ?
N3 C1 1.474(6) . ?
N3 H3N 0.879(14) . ?
N4 C3 1.350(7) . ?
N4 H4NA 0.879(14) . ?
N4 H4NB 0.881(14) . ?
N5 C2 1.382(6) . ?
N5 C10 1.396(6) . ?
N5 H5N 0.880(14) . ?
N6 C17 1.297(7) . ?
N6 C16 1.463(6) . ?
N7 C18 1.318(6) . ?
N7 C17 1.388(6) . ?
N8 C18 1.336(7) . ?
N8 C16 1.452(6) . ?
N8 H8N 0.878(14) . ?
N9 C18 1.351(7) . ?
N9 H9NA 0.878(14) . ?
N9 H9NB 0.876(14) . ?
N10 C17 1.379(6) . ?
N10 C25 1.405(7) . ?
N10 H10N 0.878(14) . ?
C1 C4 1.533(7) . ?
C1 H1 1.0000 . ?
C4 C9 1.374(8) . ?
C4 C5 1.384(8) . ?
C5 C6 1.391(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.349(11) . ?
C6 H6 0.9500 . ?
C7 C8 1.371(10) . ?
C7 H7 0.9500 . ?
C8 C9 1.408(8) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.402(7) . ?
C10 C15 1.404(7) . ?
C11 C12 1.386(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.365(7) . ?
C14 C15 1.386(7) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C19 1.542(7) . ?
C16 H16 1.0000 . ?
C19 C20 1.385(8) . ?
C19 C24 1.392(7) . ?
C20 C21 1.387(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(9) . ?
C21 H21 0.9500 . ?
C22 C23 1.368(9) . ?
C22 H22 0.9500 . ?
C23 C24 1.402(8) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.386(8) . ?
C25 C30 1.409(7) . ?
C26 C27 1.399(7) . ?
C26 H26 0.9500 . ?
C27 C28 1.385(8) . ?
C27 H27 0.9500 . ?
C28 C29 1.373(8) . ?
C29 C30 1.387(7) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.504(8) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.490(10) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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
C31 O1 H1O 112(4) . . ?
C33 O2 H2O 109(5) . . ?
C2 N1 C1 115.6(4) . . ?
C3 N2 C2 113.6(4) . . ?
C3 N3 C1 118.4(4) . . ?
C3 N3 H3N 132(4) . . ?
C1 N3 H3N 108(4) . . ?
C3 N4 H4NA 118(4) . . ?
C3 N4 H4NB 118(4) . . ?
H4NA N4 H4NB 124(6) . . ?
C2 N5 C10 128.8(4) . . ?
C2 N5 H5N 115(4) . . ?
C10 N5 H5N 116(4) . . ?
C17 N6 C16 114.6(4) . . ?
C18 N7 C17 114.9(4) . . ?
C18 N8 C16 118.2(4) . . ?
C18 N8 H8N 128(4) . . ?
C16 N8 H8N 113(4) . . ?
C18 N9 H9NA 113(4) . . ?
C18 N9 H9NB 122(4) . . ?
H9NA N9 H9NB 122(6) . . ?
C17 N10 C25 128.4(4) . . ?
C17 N10 H10N 112(4) . . ?
C25 N10 H10N 120(4) . . ?
N1 C1 N3 110.5(4) . . ?
N1 C1 C4 112.6(4) . . ?
N3 C1 C4 110.4(4) . . ?
N1 C1 H1 107.7 . . ?
N3 C1 H1 107.7 . . ?
C4 C1 H1 107.7 . . ?
N1 C2 N2 128.1(4) . . ?
N1 C2 N5 120.7(4) . . ?
N2 C2 N5 111.2(4) . . ?
N3 C3 N2 123.3(4) . . ?
N3 C3 N4 118.4(4) . . ?
N2 C3 N4 118.2(4) . . ?
C9 C4 C5 119.3(5) . . ?
C9 C4 C1 121.6(5) . . ?
C5 C4 C1 118.9(5) . . ?
C4 C5 C6 120.0(6) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 120.8(6) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.2(5) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C9 119.9(6) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C4 C9 C8 119.8(5) . . ?
C4 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
N5 C10 C11 117.0(4) . . ?
N5 C10 C15 125.2(4) . . ?
C11 C10 C15 117.7(4) . . ?
C12 C11 C10 121.3(5) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C11 119.2(4) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 120.9(5) . . ?
C14 C13 Br1 119.3(4) . . ?
C12 C13 Br1 119.8(4) . . ?
C13 C14 C15 120.4(5) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.3(5) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
N8 C16 N6 111.0(4) . . ?
N8 C16 C19 113.5(4) . . ?
N6 C16 C19 110.1(4) . . ?
N8 C16 H16 107.3 . . ?
N6 C16 H16 107.3 . . ?
C19 C16 H16 107.3 . . ?
N6 C17 N10 121.3(4) . . ?
N6 C17 N7 126.9(4) . . ?
N10 C17 N7 111.7(4) . . ?
N7 C18 N8 122.6(4) . . ?
N7 C18 N9 119.4(5) . . ?
N8 C18 N9 117.9(4) . . ?
C20 C19 C24 119.2(5) . . ?
C20 C19 C16 119.5(4) . . ?
C24 C19 C16 121.2(5) . . ?
C19 C20 C21 121.0(5) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C20 119.6(6) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C23 C22 C21 120.2(6) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.6(5) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C19 C24 C23 119.5(5) . . ?
C19 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C26 C25 N10 124.6(4) . . ?
C26 C25 C30 119.0(5) . . ?
N10 C25 C30 116.3(5) . . ?
C25 C26 C27 120.3(5) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C28 C27 C26 119.6(5) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C29 C28 C27 120.9(5) . . ?
C29 C28 Br2 120.6(4) . . ?
C27 C28 Br2 118.5(4) . . ?
C28 C29 C30 120.0(5) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C29 C30 C25 120.2(5) . . ?
C29 C30 H30 119.9 . . ?
C25 C30 H30 119.9 . . ?
O1 C31 C32 113.0(4) . . ?
O1 C31 H31A 109.0 . . ?
C32 C31 H31A 109.0 . . ?
O1 C31 H31B 109.0 . . ?
C32 C31 H31B 109.0 . . ?
H31A C31 H31B 107.8 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O2 C33 C34 113.2(5) . . ?
O2 C33 H33A 108.9 . . ?
C34 C33 H33A 108.9 . . ?
O2 C33 H33B 108.9 . . ?
C34 C33 H33B 108.9 . . ?
H33A C33 H33B 107.7 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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
C2 N1 C1 N3 -31.1(6) . . . . ?
C2 N1 C1 C4 92.9(5) . . . . ?
C3 N3 C1 N1 36.1(6) . . . . ?
C3 N3 C1 C4 -89.1(5) . . . . ?
C1 N1 C2 N2 9.8(7) . . . . ?
C1 N1 C2 N5 -172.2(4) . . . . ?
C3 N2 C2 N1 10.4(7) . . . . ?
C3 N2 C2 N5 -167.8(4) . . . . ?
C10 N5 C2 N1 23.1(7) . . . . ?
C10 N5 C2 N2 -158.6(4) . . . . ?
C1 N3 C3 N2 -18.3(7) . . . . ?
C1 N3 C3 N4 165.1(4) . . . . ?
C2 N2 C3 N3 -5.5(7) . . . . ?
C2 N2 C3 N4 171.0(4) . . . . ?
N1 C1 C4 C9 -36.0(6) . . . . ?
N3 C1 C4 C9 88.0(6) . . . . ?
N1 C1 C4 C5 148.8(5) . . . . ?
N3 C1 C4 C5 -87.2(6) . . . . ?
C9 C4 C5 C6 -0.8(8) . . . . ?
C1 C4 C5 C6 174.5(5) . . . . ?
C4 C5 C6 C7 2.2(10) . . . . ?
C5 C6 C7 C8 -1.6(10) . . . . ?
C6 C7 C8 C9 -0.4(10) . . . . ?
C5 C4 C9 C8 -1.1(8) . . . . ?
C1 C4 C9 C8 -176.3(5) . . . . ?
C7 C8 C9 C4 1.7(9) . . . . ?
C2 N5 C10 C11 -179.3(4) . . . . ?
C2 N5 C10 C15 2.7(8) . . . . ?
N5 C10 C11 C12 -179.8(4) . . . . ?
C15 C10 C11 C12 -1.7(7) . . . . ?
C10 C11 C12 C13 -0.9(7) . . . . ?
C11 C12 C13 C14 2.6(7) . . . . ?
C11 C12 C13 Br1 -177.6(4) . . . . ?
C12 C13 C14 C15 -1.5(8) . . . . ?
Br1 C13 C14 C15 178.7(4) . . . . ?
C13 C14 C15 C10 -1.3(8) . . . . ?
N5 C10 C15 C14 -179.3(5) . . . . ?
C11 C10 C15 C14 2.8(7) . . . . ?
C18 N8 C16 N6 -37.1(6) . . . . ?
C18 N8 C16 C19 87.6(5) . . . . ?
C17 N6 C16 N8 33.9(6) . . . . ?
C17 N6 C16 C19 -92.7(5) . . . . ?
C16 N6 C17 N10 171.9(4) . . . . ?
C16 N6 C17 N7 -11.4(7) . . . . ?
C25 N10 C17 N6 -24.0(8) . . . . ?
C25 N10 C17 N7 158.8(5) . . . . ?
C18 N7 C17 N6 -11.6(7) . . . . ?
C18 N7 C17 N10 165.4(4) . . . . ?
C17 N7 C18 N8 9.1(7) . . . . ?
C17 N7 C18 N9 -167.6(4) . . . . ?
C16 N8 C18 N7 15.9(7) . . . . ?
C16 N8 C18 N9 -167.3(4) . . . . ?
N8 C16 C19 C20 -170.0(5) . . . . ?
N6 C16 C19 C20 -44.9(6) . . . . ?
N8 C16 C19 C24 14.2(7) . . . . ?
N6 C16 C19 C24 139.3(5) . . . . ?
C24 C19 C20 C21 0.4(8) . . . . ?
C16 C19 C20 C21 -175.5(5) . . . . ?
C19 C20 C21 C22 0.1(9) . . . . ?
C20 C21 C22 C23 -0.6(10) . . . . ?
C21 C22 C23 C24 0.5(11) . . . . ?
C20 C19 C24 C23 -0.4(8) . . . . ?
C16 C19 C24 C23 175.4(5) . . . . ?
C22 C23 C24 C19 0.0(10) . . . . ?
C17 N10 C25 C26 -2.5(8) . . . . ?
C17 N10 C25 C30 179.0(5) . . . . ?
N10 C25 C26 C27 -177.6(5) . . . . ?
C30 C25 C26 C27 0.8(7) . . . . ?
C25 C26 C27 C28 0.2(8) . . . . ?
C26 C27 C28 C29 -1.1(8) . . . . ?
C26 C27 C28 Br2 177.2(4) . . . . ?
C27 C28 C29 C30 0.8(8) . . . . ?
Br2 C28 C29 C30 -177.4(4) . . . . ?
C28 C29 C30 C25 0.3(8) . . . . ?
C26 C25 C30 C29 -1.1(7) . . . . ?
N10 C25 C30 C29 177.5(5) . . . . ?

_refine_diff_density_max         0.742
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_A_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1961318'
loop_
_audit_author_name
_audit_author_address
'Edward Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2019-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 Cl N5, C2 H6 O'
_chemical_formula_sum            'C17 H20 Cl N5 O'
_chemical_formula_weight         345.83

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   12.6684(2)
_cell_length_b                   9.81230(10)
_cell_length_c                   15.0780(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.8020(10)
_cell_angle_gamma                90
_cell_volume                     1763.46(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    20482
_cell_measurement_theta_min      3.6920
_cell_measurement_theta_max      76.3650

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.064
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    2.030
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_reflns_number            42215
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.115
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_full        67.074
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6286
_reflns_number_gt                6062
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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 1.171.39.31a (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0406P)²+0.3076P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2733 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6286
_refine_ls_number_parameters     465
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0731
_refine_ls_wR_factor_gt          0.0719
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.066
_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
Cl1 Cl 0.10187(5) 0.19909(8) -0.35949(4) 0.03154(16) Uani 1 1 d . . . . .
Cl2 Cl 0.92885(6) 0.20536(10) 0.38435(5) 0.0440(2) Uani 1 1 d . . . . .
O1 O 0.60396(15) 0.66334(18) 0.47581(12) 0.0232(4) Uani 1 1 d D . . . .
H1O H 0.626(2) 0.622(3) 0.5278(14) 0.028 Uiso 1 1 d D U . . .
O2 O 0.38783(14) 0.65258(17) 0.91100(11) 0.0198(4) Uani 1 1 d D . . . .
H2O H 0.371(2) 0.616(3) 0.9551(16) 0.024 Uiso 1 1 d D U . . .
N1 N 0.35612(17) 0.5321(2) 0.06293(13) 0.0171(4) Uani 1 1 d . . . . .
N2 N 0.47363(16) 0.3812(2) 0.18195(13) 0.0180(4) Uani 1 1 d . . . . .
N3 N 0.45101(16) 0.6076(2) 0.22148(13) 0.0175(4) Uani 1 1 d D . . . .
H3N H 0.470(2) 0.677(2) 0.2599(17) 0.021 Uiso 1 1 d D U . . .
N4 N 0.56897(19) 0.4626(2) 0.33071(14) 0.0229(4) Uani 1 1 d D . . . .
H4NA H 0.600(2) 0.3811(19) 0.343(2) 0.027 Uiso 1 1 d D U . . .
H4NB H 0.576(3) 0.523(3) 0.3751(17) 0.027 Uiso 1 1 d D U . . .
N5 N 0.40983(17) 0.3178(2) 0.02735(14) 0.0181(4) Uani 1 1 d D . . . .
H5N H 0.4652(18) 0.259(2) 0.047(2) 0.022 Uiso 1 1 d D U . . .
N6 N 0.64830(17) 0.5382(2) 0.64450(13) 0.0177(4) Uani 1 1 d . . . . .
N7 N 0.53661(17) 0.3808(2) 0.69699(13) 0.0185(4) Uani 1 1 d . . . . .
N8 N 0.55137(16) 0.6071(2) 0.74906(13) 0.0178(4) Uani 1 1 d D . . . .
H8N H 0.527(2) 0.677(2) 0.7725(19) 0.021 Uiso 1 1 d D U . . .
N9 N 0.4315(2) 0.4578(2) 0.78531(15) 0.0235(5) Uani 1 1 d D . . . .
H9NA H 0.403(3) 0.3759(19) 0.775(2) 0.028 Uiso 1 1 d D U . . .
H9NB H 0.420(3) 0.516(3) 0.8253(18) 0.028 Uiso 1 1 d D U . . .
N10 N 0.60245(18) 0.3221(2) 0.57885(14) 0.0199(4) Uani 1 1 d D . . . .
H10N H 0.5482(19) 0.261(2) 0.566(2) 0.024 Uiso 1 1 d D U . . .
C1 C 0.3508(2) 0.6228(2) 0.13711(16) 0.0176(5) Uani 1 1 d . . . . .
H1 H 0.349756 0.718445 0.113846 0.021 Uiso 1 1 calc R U . . .
C2 C 0.40986(19) 0.4179(2) 0.09097(16) 0.0161(5) Uani 1 1 d . . . . .
C3 C 0.4952(2) 0.4841(3) 0.24367(16) 0.0170(5) Uani 1 1 d . . . . .
C4 C 0.24576(19) 0.6026(3) 0.16317(16) 0.0194(5) Uani 1 1 d . . . . .
C5 C 0.1986(2) 0.7136(3) 0.1922(2) 0.0361(7) Uani 1 1 d . . . . .
H5 H 0.228439 0.802174 0.190997 0.043 Uiso 1 1 calc R U . . .
C6 C 0.1082(2) 0.6966(4) 0.2231(3) 0.0474(9) Uani 1 1 d . . . . .
H6 H 0.077116 0.773406 0.243691 0.057 Uiso 1 1 calc R U . . .
C7 C 0.0631(2) 0.5700(4) 0.2243(2) 0.0399(8) Uani 1 1 d . . . . .
H7 H 0.000970 0.559092 0.245368 0.048 Uiso 1 1 calc R U . . .
C8 C 0.1083(3) 0.4588(3) 0.1948(2) 0.0357(7) Uani 1 1 d . . . . .
H8 H 0.077049 0.370852 0.195206 0.043 Uiso 1 1 calc R U . . .
C9 C 0.1999(2) 0.4749(3) 0.1643(2) 0.0287(6) Uani 1 1 d . . . . .
H9 H 0.231067 0.397715 0.144244 0.034 Uiso 1 1 calc R U . . .
C10 C 0.3330(2) 0.2947(2) -0.06357(16) 0.0172(5) Uani 1 1 d . . . . .
C11 C 0.2367(2) 0.3718(3) -0.10568(17) 0.0204(5) Uani 1 1 d . . . . .
H11 H 0.219027 0.445360 -0.072173 0.024 Uiso 1 1 calc R U . . .
C12 C 0.1664(2) 0.3417(3) -0.19651(18) 0.0227(5) Uani 1 1 d . . . . .
H12 H 0.101515 0.395642 -0.225380 0.027 Uiso 1 1 calc R U . . .
C13 C 0.1905(2) 0.2333(3) -0.24493(16) 0.0221(5) Uani 1 1 d . . . . .
C14 C 0.2837(2) 0.1533(3) -0.20349(17) 0.0224(5) Uani 1 1 d . . . . .
H14 H 0.299162 0.077788 -0.236608 0.027 Uiso 1 1 calc R U . . .
C15 C 0.35481(19) 0.1836(3) -0.11321(16) 0.0202(5) Uani 1 1 d . . . . .
H15 H 0.419024 0.128507 -0.084665 0.024 Uiso 1 1 calc R U . . .
C16 C 0.6516(2) 0.6255(2) 0.72360(16) 0.0174(5) Uani 1 1 d . . . . .
H16 H 0.651494 0.722012 0.702250 0.021 Uiso 1 1 calc R U . . .
C17 C 0.5992(2) 0.4214(2) 0.64266(16) 0.0171(5) Uani 1 1 d . . . . .
C18 C 0.5087(2) 0.4813(3) 0.74395(16) 0.0175(5) Uani 1 1 d . . . . .
C19 C 0.7603(2) 0.6039(3) 0.80644(16) 0.0196(5) Uani 1 1 d . . . . .
C20 C 0.8621(2) 0.5986(3) 0.78988(19) 0.0268(5) Uani 1 1 d . . . . .
H20 H 0.862444 0.602935 0.727051 0.032 Uiso 1 1 calc R U . . .
C21 C 0.9624(2) 0.5871(3) 0.8639(2) 0.0372(7) Uani 1 1 d . . . . .
H21 H 1.031025 0.582253 0.851571 0.045 Uiso 1 1 calc R U . . .
C22 C 0.9630(3) 0.5828(4) 0.9563(2) 0.0418(8) Uani 1 1 d . . . . .
H22 H 1.031968 0.576981 1.007209 0.050 Uiso 1 1 calc R U . . .
C23 C 0.8634(3) 0.5869(4) 0.9733(2) 0.0371(7) Uani 1 1 d . . . . .
H23 H 0.863580 0.582427 1.036347 0.045 Uiso 1 1 calc R U . . .
C24 C 0.7621(2) 0.5975(3) 0.89930(18) 0.0269(5) Uani 1 1 d . . . . .
H24 H 0.693643 0.600358 0.912053 0.032 Uiso 1 1 calc R U . . .
C25 C 0.6803(2) 0.3033(3) 0.53270(16) 0.0199(5) Uani 1 1 d . . . . .
C26 C 0.7750(2) 0.3839(3) 0.54638(17) 0.0236(5) Uani 1 1 d . . . . .
H26 H 0.788250 0.459852 0.587795 0.028 Uiso 1 1 calc R U . . .
C27 C 0.8503(2) 0.3544(3) 0.50007(18) 0.0278(6) Uani 1 1 d . . . . .
H27 H 0.914641 0.410077 0.509755 0.033 Uiso 1 1 calc R U . . .
C28 C 0.8312(2) 0.2433(3) 0.43959(18) 0.0287(6) Uani 1 1 d . . . . .
C29 C 0.7373(2) 0.1636(3) 0.42371(18) 0.0282(6) Uani 1 1 d . . . . .
H29 H 0.724078 0.088846 0.381336 0.034 Uiso 1 1 calc R U . . .
C30 C 0.6617(2) 0.1929(3) 0.46987(16) 0.0229(5) Uani 1 1 d . . . . .
H30 H 0.596903 0.137685 0.458835 0.028 Uiso 1 1 calc R U . . .
C31 C 0.6979(2) 0.7439(3) 0.4754(2) 0.0336(7) Uani 1 1 d . . . . .
H31A H 0.678259 0.792853 0.414499 0.040 Uiso 1 1 calc R U . . .
H31B H 0.761706 0.682674 0.480162 0.040 Uiso 1 1 calc R U . . .
C32 C 0.7340(3) 0.8458(4) 0.5541(3) 0.0511(9) Uani 1 1 d . . . . .
H32A H 0.794694 0.902143 0.547405 0.077 Uiso 1 1 calc R U . . .
H32B H 0.760624 0.797746 0.614676 0.077 Uiso 1 1 calc R U . . .
H32C H 0.670245 0.903991 0.551800 0.077 Uiso 1 1 calc R U . . .
C33 C 0.2900(2) 0.7230(3) 0.85125(17) 0.0249(5) Uani 1 1 d . . . . .
H33A H 0.232688 0.655138 0.817384 0.030 Uiso 1 1 calc R U . . .
H33B H 0.310419 0.776087 0.803613 0.030 Uiso 1 1 calc R U . . .
C34 C 0.2406(3) 0.8175(3) 0.9052(2) 0.0368(7) Uani 1 1 d . . . . .
H34A H 0.178295 0.868458 0.860926 0.055 Uiso 1 1 calc R U . . .
H34B H 0.298263 0.881426 0.941977 0.055 Uiso 1 1 calc R U . . .
H34C H 0.212867 0.764386 0.947780 0.055 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
Cl1 C13 1.744(2) . ?
Cl2 C28 1.749(3) . ?
O1 C31 1.431(3) . ?
O1 H1O 0.840(14) . ?
O2 C33 1.438(3) . ?
O2 H2O 0.843(14) . ?
N1 C2 1.305(3) . ?
N1 C1 1.449(3) . ?
N2 C3 1.337(3) . ?
N2 C2 1.383(3) . ?
N3 C3 1.329(3) . ?
N3 C1 1.469(3) . ?
N3 H3N 0.873(14) . ?
N4 C3 1.345(3) . ?
N4 H4NA 0.882(14) . ?
N4 H4NB 0.879(14) . ?
N5 C2 1.373(3) . ?
N5 C10 1.405(3) . ?
N5 H5N 0.879(13) . ?
N6 C17 1.300(3) . ?
N6 C16 1.458(3) . ?
N7 C18 1.330(3) . ?
N7 C17 1.378(3) . ?
N8 C18 1.339(3) . ?
N8 C16 1.456(3) . ?
N8 H8N 0.877(14) . ?
N9 C18 1.345(3) . ?
N9 H9NA 0.875(14) . ?
N9 H9NB 0.879(14) . ?
N10 C17 1.379(3) . ?
N10 C25 1.399(3) . ?
N10 H10N 0.884(14) . ?
C1 C4 1.523(3) . ?
C1 H1 1.0000 . ?
C4 C9 1.383(4) . ?
C4 C5 1.383(4) . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.370(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.395(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.393(4) . ?
C10 C15 1.401(3) . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(4) . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C19 1.529(3) . ?
C16 H16 1.0000 . ?
C19 C20 1.394(4) . ?
C19 C24 1.394(4) . ?
C20 C21 1.382(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.371(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.392(4) . ?
C25 C30 1.406(4) . ?
C26 C27 1.391(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.389(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.375(4) . ?
C29 C30 1.391(4) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.500(5) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.504(4) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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
C31 O1 H1O 105(2) . . ?
C33 O2 H2O 107(2) . . ?
C2 N1 C1 115.67(19) . . ?
C3 N2 C2 114.0(2) . . ?
C3 N3 C1 118.5(2) . . ?
C3 N3 H3N 123.1(19) . . ?
C1 N3 H3N 117.2(19) . . ?
C3 N4 H4NA 117(2) . . ?
C3 N4 H4NB 119(2) . . ?
H4NA N4 H4NB 123(3) . . ?
C2 N5 C10 129.3(2) . . ?
C2 N5 H5N 115.3(19) . . ?
C10 N5 H5N 115.4(19) . . ?
C17 N6 C16 114.63(19) . . ?
C18 N7 C17 114.4(2) . . ?
C18 N8 C16 118.1(2) . . ?
C18 N8 H8N 123.3(19) . . ?
C16 N8 H8N 118.3(19) . . ?
C18 N9 H9NA 114(2) . . ?
C18 N9 H9NB 121(2) . . ?
H9NA N9 H9NB 124(3) . . ?
C17 N10 C25 129.2(2) . . ?
C17 N10 H10N 115(2) . . ?
C25 N10 H10N 115(2) . . ?
N1 C1 N3 110.70(19) . . ?
N1 C1 C4 113.09(19) . . ?
N3 C1 C4 109.73(18) . . ?
N1 C1 H1 107.7 . . ?
N3 C1 H1 107.7 . . ?
C4 C1 H1 107.7 . . ?
N1 C2 N5 120.8(2) . . ?
N1 C2 N2 127.6(2) . . ?
N5 C2 N2 111.6(2) . . ?
N3 C3 N2 122.9(2) . . ?
N3 C3 N4 118.9(2) . . ?
N2 C3 N4 118.1(2) . . ?
C9 C4 C5 118.8(2) . . ?
C9 C4 C1 121.9(2) . . ?
C5 C4 C1 119.2(2) . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 120.0(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C4 C9 C8 120.5(3) . . ?
C4 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C15 118.7(2) . . ?
C11 C10 N5 124.6(2) . . ?
C15 C10 N5 116.7(2) . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 Cl1 120.29(19) . . ?
C12 C13 Cl1 119.19(19) . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C10 120.8(2) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
N8 C16 N6 110.92(19) . . ?
N8 C16 C19 113.09(19) . . ?
N6 C16 C19 110.77(19) . . ?
N8 C16 H16 107.3 . . ?
N6 C16 H16 107.3 . . ?
C19 C16 H16 107.3 . . ?
N6 C17 N7 127.5(2) . . ?
N6 C17 N10 120.7(2) . . ?
N7 C17 N10 111.7(2) . . ?
N7 C18 N8 122.6(2) . . ?
N7 C18 N9 119.1(2) . . ?
N8 C18 N9 118.3(2) . . ?
C20 C19 C24 118.5(2) . . ?
C20 C19 C16 119.4(2) . . ?
C24 C19 C16 122.0(2) . . ?
C21 C20 C19 120.8(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 120.1(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C23 C22 C21 119.6(3) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C19 120.4(3) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C26 C25 N10 124.7(2) . . ?
C26 C25 C30 118.5(2) . . ?
N10 C25 C30 116.8(2) . . ?
C27 C26 C25 120.7(2) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C28 C27 C26 119.8(3) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C29 C28 C27 120.6(2) . . ?
C29 C28 Cl2 120.4(2) . . ?
C27 C28 Cl2 119.0(2) . . ?
C28 C29 C30 119.8(2) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C29 C30 C25 120.6(2) . . ?
C29 C30 H30 119.7 . . ?
C25 C30 H30 119.7 . . ?
O1 C31 C32 113.3(2) . . ?
O1 C31 H31A 108.9 . . ?
C32 C31 H31A 108.9 . . ?
O1 C31 H31B 108.9 . . ?
C32 C31 H31B 108.9 . . ?
H31A C31 H31B 107.7 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O2 C33 C34 112.7(2) . . ?
O2 C33 H33A 109.0 . . ?
C34 C33 H33A 109.0 . . ?
O2 C33 H33B 109.0 . . ?
C34 C33 H33B 109.0 . . ?
H33A C33 H33B 107.8 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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
C2 N1 C1 N3 30.8(3) . . . . ?
C2 N1 C1 C4 -92.8(2) . . . . ?
C3 N3 C1 N1 -36.6(3) . . . . ?
C3 N3 C1 C4 88.9(2) . . . . ?
C1 N1 C2 N5 172.8(2) . . . . ?
C1 N1 C2 N2 -8.8(3) . . . . ?
C10 N5 C2 N1 -22.5(4) . . . . ?
C10 N5 C2 N2 158.9(2) . . . . ?
C3 N2 C2 N1 -11.2(3) . . . . ?
C3 N2 C2 N5 167.3(2) . . . . ?
C1 N3 C3 N2 18.7(3) . . . . ?
C1 N3 C3 N4 -164.5(2) . . . . ?
C2 N2 C3 N3 5.7(3) . . . . ?
C2 N2 C3 N4 -171.1(2) . . . . ?
N1 C1 C4 C9 36.9(3) . . . . ?
N3 C1 C4 C9 -87.2(3) . . . . ?
N1 C1 C4 C5 -147.2(2) . . . . ?
N3 C1 C4 C5 88.6(3) . . . . ?
C9 C4 C5 C6 0.9(4) . . . . ?
C1 C4 C5 C6 -175.1(3) . . . . ?
C4 C5 C6 C7 -0.8(5) . . . . ?
C5 C6 C7 C8 0.2(5) . . . . ?
C6 C7 C8 C9 0.3(5) . . . . ?
C5 C4 C9 C8 -0.4(4) . . . . ?
C1 C4 C9 C8 175.5(2) . . . . ?
C7 C8 C9 C4 -0.2(4) . . . . ?
C2 N5 C10 C11 -2.0(4) . . . . ?
C2 N5 C10 C15 179.7(2) . . . . ?
C15 C10 C11 C12 -2.4(4) . . . . ?
N5 C10 C11 C12 179.4(2) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C11 C12 C13 Cl1 -179.1(2) . . . . ?
C12 C13 C14 C15 -1.3(4) . . . . ?
Cl1 C13 C14 C15 178.52(19) . . . . ?
C13 C14 C15 C10 0.0(4) . . . . ?
C11 C10 C15 C14 1.8(3) . . . . ?
N5 C10 C15 C14 -179.8(2) . . . . ?
C18 N8 C16 N6 37.3(3) . . . . ?
C18 N8 C16 C19 -87.8(2) . . . . ?
C17 N6 C16 N8 -33.8(3) . . . . ?
C17 N6 C16 C19 92.7(2) . . . . ?
C16 N6 C17 N7 10.8(3) . . . . ?
C16 N6 C17 N10 -171.8(2) . . . . ?
C18 N7 C17 N6 12.4(3) . . . . ?
C18 N7 C17 N10 -165.2(2) . . . . ?
C25 N10 C17 N6 23.9(4) . . . . ?
C25 N10 C17 N7 -158.4(2) . . . . ?
C17 N7 C18 N8 -9.4(3) . . . . ?
C17 N7 C18 N9 168.2(2) . . . . ?
C16 N8 C18 N7 -16.0(3) . . . . ?
C16 N8 C18 N9 166.4(2) . . . . ?
N8 C16 C19 C20 170.8(2) . . . . ?
N6 C16 C19 C20 45.5(3) . . . . ?
N8 C16 C19 C24 -13.2(3) . . . . ?
N6 C16 C19 C24 -138.5(2) . . . . ?
C24 C19 C20 C21 0.1(4) . . . . ?
C16 C19 C20 C21 176.2(3) . . . . ?
C19 C20 C21 C22 -1.0(5) . . . . ?
C20 C21 C22 C23 1.4(5) . . . . ?
C21 C22 C23 C24 -1.0(5) . . . . ?
C22 C23 C24 C19 0.1(5) . . . . ?
C20 C19 C24 C23 0.4(4) . . . . ?
C16 C19 C24 C23 -175.7(3) . . . . ?
C17 N10 C25 C26 2.2(4) . . . . ?
C17 N10 C25 C30 -179.3(2) . . . . ?
N10 C25 C26 C27 177.5(2) . . . . ?
C30 C25 C26 C27 -1.0(4) . . . . ?
C25 C26 C27 C28 -0.1(4) . . . . ?
C26 C27 C28 C29 1.2(4) . . . . ?
C26 C27 C28 Cl2 -178.4(2) . . . . ?
C27 C28 C29 C30 -1.2(4) . . . . ?
Cl2 C28 C29 C30 178.4(2) . . . . ?
C28 C29 C30 C25 0.0(4) . . . . ?
C26 C25 C30 C29 1.1(4) . . . . ?
N10 C25 C30 C29 -177.5(2) . . . . ?

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.042

