# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 1915780'
_audit_update_record             
;
2020-02-02 deposited with the CCDC.	2020-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 N4 O'
_chemical_formula_weight         262.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'

_cell_length_a                   6.6568(17)
_cell_length_b                   11.350(3)
_cell_length_c                   16.471(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1244.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1092
_cell_measurement_theta_min      2.176
_cell_measurement_theta_max      21.665

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9727
_diffrn_reflns_av_unetI/netI     0.0940
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.473
_diffrn_reflns_theta_max         27.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2992
_reflns_number_gt                1348
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_max     0.999
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0380P)²+0.5201P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 363 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.5(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2992
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1699
_refine_ls_R_factor_gt           0.0750
_refine_ls_wR_factor_ref         0.1780
_refine_ls_wR_factor_gt          0.1514
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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
O1 O 0.5340(7) 0.2784(3) 0.36076(17) 0.0432(10) Uani 1 1 d . . . . .
H1 H 0.534110 0.350586 0.362199 0.065 Uiso 1 1 calc R U . . .
N4 N 0.5205(7) 0.4849(3) 0.4265(2) 0.0350(11) Uani 1 1 d . . . . .
C4 C 0.5032(9) 0.6070(4) 0.4225(2) 0.0313(12) Uani 1 1 d . . . . .
C5 C 0.5256(8) 0.4324(4) 0.4969(3) 0.0322(12) Uani 1 1 d . . . . .
H5 H 0.525364 0.478061 0.543791 0.039 Uiso 1 1 calc R U . . .
N3 N 0.4938(12) 0.6030(3) 0.2775(2) 0.0631(17) Uani 1 1 d . . . . .
H3A H 0.505549 0.527564 0.276216 0.076 Uiso 1 1 calc R U . . .
H3B H 0.484542 0.642173 0.232984 0.076 Uiso 1 1 calc R U . . .
C6 C 0.5314(9) 0.3071(4) 0.5045(3) 0.0324(12) Uani 1 1 d . . . . .
C11 C 0.5343(9) 0.2534(4) 0.5841(3) 0.0358(13) Uani 1 1 d . . . . .
C7 C 0.5344(10) 0.2356(4) 0.4370(3) 0.0354(13) Uani 1 1 d . . . . .
C10 C 0.5334(10) 0.1287(4) 0.5889(3) 0.0372(13) Uani 1 1 d . . . . .
N2 N 0.4889(11) 0.7302(4) 0.5527(2) 0.0689(17) Uani 1 1 d . . . . .
C2 C 0.4899(11) 0.6593(4) 0.3487(3) 0.0480(17) Uani 1 1 d . . . . .
C9 C 0.5326(9) 0.0622(5) 0.5175(3) 0.0438(14) Uani 1 1 d . . . . .
H9 H 0.532160 -0.019592 0.521357 0.053 Uiso 1 1 calc R U . . .
C8 C 0.5325(10) 0.1122(4) 0.4431(3) 0.0433(15) Uani 1 1 d . . . . .
H8 H 0.531117 0.065631 0.396656 0.052 Uiso 1 1 calc R U . . .
C3 C 0.4935(12) 0.6772(4) 0.4940(3) 0.0471(16) Uani 1 1 d . . . . .
C15 C 0.5324(11) 0.0732(5) 0.6649(3) 0.0525(17) Uani 1 1 d . . . . .
H15 H 0.528010 -0.008548 0.667838 0.063 Uiso 1 1 calc R U . . .
C12 C 0.5364(10) 0.3165(5) 0.6571(3) 0.0467(15) Uani 1 1 d . . . . .
H12 H 0.538145 0.398363 0.655810 0.056 Uiso 1 1 calc R U . . .
C1 C 0.4678(13) 0.7837(5) 0.3431(3) 0.0555(18) Uani 1 1 d . . . . .
N1 N 0.4469(12) 0.8837(5) 0.3335(3) 0.085(2) Uani 1 1 d . . . . .
C13 C 0.5361(13) 0.2598(5) 0.7297(3) 0.0592(19) Uani 1 1 d . . . . .
H13 H 0.534727 0.303707 0.777416 0.071 Uiso 1 1 calc R U . . .
C14 C 0.5376(14) 0.1376(5) 0.7342(3) 0.063(2) Uani 1 1 d . . . . .
H14 H 0.542170 0.100149 0.784439 0.076 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 C7 1.346(5) . ?
O1 H1 0.8200 . ?
N4 C5 1.304(5) . ?
N4 C4 1.392(5) . ?
C4 C2 1.356(6) . ?
C4 C3 1.422(6) . ?
C5 C6 1.428(6) . ?
C5 H5 0.9300 . ?
N3 C2 1.336(6) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
C6 C7 1.376(6) . ?
C6 C11 1.446(6) . ?
C11 C12 1.399(6) . ?
C11 C10 1.418(6) . ?
C7 C8 1.405(6) . ?
C10 C9 1.398(7) . ?
C10 C15 1.401(7) . ?
N2 C3 1.139(6) . ?
C2 C1 1.423(7) . ?
C9 C8 1.350(7) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C15 C14 1.356(8) . ?
C15 H15 0.9300 . ?
C12 C13 1.359(7) . ?
C12 H12 0.9300 . ?
C1 N1 1.154(7) . ?
C13 C14 1.389(7) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1 109.5 . . ?
C5 N4 C4 120.0(4) . . ?
C2 C4 N4 118.9(4) . . ?
C2 C4 C3 119.6(4) . . ?
N4 C4 C3 121.5(4) . . ?
N4 C5 C6 122.2(4) . . ?
N4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C7 C6 C5 121.2(4) . . ?
C7 C6 C11 118.9(4) . . ?
C5 C6 C11 119.9(4) . . ?
C12 C11 C10 117.5(4) . . ?
C12 C11 C6 124.3(4) . . ?
C10 C11 C6 118.2(4) . . ?
O1 C7 C6 122.7(4) . . ?
O1 C7 C8 115.2(4) . . ?
C6 C7 C8 122.0(4) . . ?
C9 C10 C15 120.6(5) . . ?
C9 C10 C11 119.4(4) . . ?
C15 C10 C11 119.9(5) . . ?
N3 C2 C4 125.2(4) . . ?
N3 C2 C1 114.8(4) . . ?
C4 C2 C1 120.0(4) . . ?
C8 C9 C10 122.4(5) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C9 C8 C7 119.0(5) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
N2 C3 C4 177.5(6) . . ?
C14 C15 C10 120.7(5) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C13 C12 C11 121.0(5) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
N1 C1 C2 175.8(6) . . ?
C12 C13 C14 121.3(5) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 119.5(5) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?

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 N4 C4 C2 -177.3(6) . . . . ?
C5 N4 C4 C3 0.9(10) . . . . ?
C4 N4 C5 C6 176.3(6) . . . . ?
N4 C5 C6 C7 0.8(9) . . . . ?
N4 C5 C6 C11 -179.2(6) . . . . ?
C7 C6 C11 C12 178.4(7) . . . . ?
C5 C6 C11 C12 -1.5(9) . . . . ?
C7 C6 C11 C10 -2.1(9) . . . . ?
C5 C6 C11 C10 178.0(6) . . . . ?
C5 C6 C7 O1 0.6(10) . . . . ?
C11 C6 C7 O1 -179.4(6) . . . . ?
C5 C6 C7 C8 -177.5(6) . . . . ?
C11 C6 C7 C8 2.5(10) . . . . ?
C12 C11 C10 C9 -179.6(6) . . . . ?
C6 C11 C10 C9 0.9(10) . . . . ?
C12 C11 C10 C15 0.7(11) . . . . ?
C6 C11 C10 C15 -178.8(6) . . . . ?
N4 C4 C2 N3 -0.7(12) . . . . ?
C3 C4 C2 N3 -178.9(8) . . . . ?
N4 C4 C2 C1 178.7(7) . . . . ?
C3 C4 C2 C1 0.4(11) . . . . ?
C15 C10 C9 C8 179.6(7) . . . . ?
C11 C10 C9 C8 -0.1(11) . . . . ?
C10 C9 C8 C7 0.4(11) . . . . ?
O1 C7 C8 C9 -179.9(5) . . . . ?
C6 C7 C8 C9 -1.6(11) . . . . ?
C9 C10 C15 C14 178.5(8) . . . . ?
C11 C10 C15 C14 -1.8(11) . . . . ?
C10 C11 C12 C13 -0.5(11) . . . . ?
C6 C11 C12 C13 179.0(6) . . . . ?
C11 C12 C13 C14 1.3(13) . . . . ?
C10 C15 C14 C13 2.5(13) . . . . ?
C12 C13 C14 C15 -2.3(15) . . . . ?

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
C8 H8 N1 0.93 2.38 3.211(7) 148.8 1_545 yes
N3 H3B O1 0.86 2.19 3.031(5) 166.2 3_655 yes
N3 H3A N1 0.86 2.46 3.114(7) 133.8 3_645 yes
O1 H1 N4 0.82 1.86 2.584(5) 146.7 . yes
C8 H8 N1 0.93 2.38 3.211(7) 148.8 1_545 yes
N3 H3B O1 0.86 2.19 3.031(5) 166.2 3_655 yes
N3 H3A N1 0.86 2.46 3.114(7) 133.8 3_645 yes
O1 H1 N4 0.82 1.86 2.584(5) 146.7 . yes
C8 H8 N1 0.93 2.38 3.211(7) 148.8 1_545 yes
N3 H3B O1 0.86 2.19 3.031(5) 166.2 3_655 yes
N3 H3A N1 0.86 2.46 3.114(7) 133.8 3_645 yes
O1 H1 N4 0.82 1.86 2.584(5) 146.7 . yes
C8 H8 N1 0.93 2.38 3.211(7) 148.8 1_545 yes
N3 H3B O1 0.86 2.19 3.031(5) 166.2 3_655 yes
N3 H3A N1 0.86 2.46 3.114(7) 133.8 3_645 yes
O1 H1 N4 0.82 1.86 2.584(5) 146.7 . yes
C8 H8 N1 0.93 2.38 3.211(7) 148.8 1_545 yes
N3 H3B O1 0.86 2.19 3.031(5) 166.2 3_655 yes
N3 H3A N1 0.86 2.46 3.114(7) 133.8 3_645 yes
O1 H1 N4 0.82 1.86 2.584(5) 146.7 . yes
C8 H8 N1 0.93 2.38 3.211(7) 148.8 1_545 yes
N3 H3B O1 0.86 2.19 3.031(5) 166.2 3_655 yes
N3 H3A N1 0.86 2.46 3.114(7) 133.8 3_645 yes
O1 H1 N4 0.82 1.86 2.584(5) 146.7 . yes
C8 H8 N1 0.93 2.38 3.211(7) 148.8 1_545 yes
N3 H3B O1 0.86 2.19 3.031(5) 166.2 3_655 yes
N3 H3A N1 0.86 2.46 3.114(7) 133.8 3_645 yes
O1 H1 N4 0.82 1.86 2.584(5) 146.7 . yes
C8 H8 N1 0.93 2.38 3.211(7) 148.8 1_545 yes
N3 H3B O1 0.86 2.19 3.031(5) 166.2 3_655 yes
N3 H3A N1 0.86 2.46 3.114(7) 133.8 3_645 yes
O1 H1 N4 0.82 1.86 2.584(5) 146.7 . yes
C8 H8 N1 0.93 2.38 3.211(7) 148.8 1_545 yes
N3 H3B O1 0.86 2.19 3.031(5) 166.2 3_655 yes
N3 H3A N1 0.86 2.46 3.114(7) 133.8 3_645 yes
O1 H1 N4 0.82 1.86 2.584(5) 146.7 . yes
C8 H8 N1 0.93 2.38 3.211(7) 148.8 1_545 yes
N3 H3B O1 0.86 2.19 3.031(5) 166.2 3_655 yes
N3 H3A N1 0.86 2.46 3.114(7) 133.8 3_645 yes
O1 H1 N4 0.82 1.86 2.584(5) 146.7 . yes
C8 H8 N1 0.93 2.38 3.211(7) 148.8 1_545 yes
N3 H3B O1 0.86 2.19 3.031(5) 166.2 3_655 yes
N3 H3A N1 0.86 2.46 3.114(7) 133.8 3_645 yes
O1 H1 N4 0.82 1.86 2.584(5) 146.7 . yes
O1 H1 N4 0.82 1.86 2.584(5) 146.7 . yes
N3 H3A N1 0.86 2.46 3.114(7) 133.8 3_645 yes
N3 H3B O1 0.86 2.19 3.031(5) 166.2 3_655 yes
C8 H8 N1 0.93 2.38 3.211(7) 148.8 1_545 yes
O1 H1 N4 0.82 1.86 2.584(5) 146.7 . yes
N3 H3A N1 0.86 2.46 3.114(7) 133.8 3_645 yes
N3 H3B O1 0.86 2.19 3.031(5) 166.2 3_655 yes
C8 H8 N1 0.93 2.38 3.211(7) 148.8 1_545 yes
O1 H1 N4 0.82 1.86 2.584(5) 146.7 . yes
N3 H3A N1 0.86 2.46 3.114(7) 133.8 3_645 yes
N3 H3B O1 0.86 2.19 3.031(5) 166.2 3_655 yes
C8 H8 N1 0.93 2.38 3.211(7) 148.8 1_545 yes

_refine_diff_density_max         0.641
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.103

####################################################################### 
# 
# 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_ZnL5ch
_database_code_depnum_ccdc_archive 'CCDC 1915781'
_audit_update_record             
;
2020-02-02 deposited with the CCDC.	2020-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H26 N10 O3 Zn2'
_chemical_formula_weight         765.40

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   10.2417(4)
_cell_length_b                   12.1827(5)
_cell_length_c                   14.1173(6)
_cell_angle_alpha                77.3880(10)
_cell_angle_beta                 88.1190(10)
_cell_angle_gamma                77.2430(10)
_cell_volume                     1676.29(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7989
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.96

_exptl_crystal_description       rodlike
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             780
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.483
_shelx_estimated_absorpt_T_min   0.673
_shelx_estimated_absorpt_T_max   0.797
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20812
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.478
_diffrn_reflns_theta_max         28.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8294
_reflns_number_gt                6430
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0396P)²+0.1514P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8294
_refine_ls_number_parameters     454
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0773
_refine_ls_wR_factor_gt          0.0719
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
Zn1 Zn 0.42258(2) 0.26798(2) 0.20605(2) 0.03273(6) Uani 1 1 d . . . . .
Zn2 Zn 0.25029(2) 0.31410(2) 0.38968(2) 0.03361(6) Uani 1 1 d . . . . .
O1 O 0.30964(13) 0.39853(10) 0.26280(9) 0.0374(3) Uani 1 1 d . . . . .
O2 O 0.34088(12) 0.18206(10) 0.32560(8) 0.0347(3) Uani 1 1 d . . . . .
O3 O 0.05417(14) 0.32162(14) 0.35569(11) 0.0596(4) Uani 1 1 d . . . . .
H3A H -0.002368 0.312718 0.406399 0.071 Uiso 1 1 d R U . . .
N1 N 0.28446(14) 0.18721(12) 0.51898(10) 0.0296(3) Uani 1 1 d . . . . .
N2 N 0.23087(17) 0.41733(13) 0.48420(12) 0.0439(4) Uani 1 1 d . . . . .
H2A H 0.215711 0.484380 0.477346 0.053 Uiso 1 1 d R U . . .
N3 N 0.2635(2) 0.11779(16) 0.77068(13) 0.0623(5) Uani 1 1 d . . . . .
N4 N 0.2291(3) 0.46182(19) 0.71888(16) 0.0795(7) Uani 1 1 d . . . . .
N6 N 0.59757(16) 0.16225(12) 0.18847(11) 0.0382(4) Uani 1 1 d . . . . .
H6A H 0.616546 0.098050 0.195571 0.046 Uiso 1 1 d R U . . .
N7 N 0.53552(14) 0.39312(12) 0.15134(10) 0.0314(3) Uani 1 1 d . . . . .
N8 N 0.8295(2) 0.45393(17) 0.03922(16) 0.0635(5) Uani 1 1 d . . . . .
N9 N 0.9317(2) 0.11628(18) 0.12021(17) 0.0684(6) Uani 1 1 d . . . . .
N10 N 0.29272(17) 0.26833(14) 0.09492(12) 0.0450(4) Uani 1 1 d . . . . .
C1 C 0.3483(2) -0.17391(15) 0.57314(13) 0.0387(4) Uani 1 1 d . . . . .
H1 H 0.327251 -0.134558 0.623065 0.046 Uiso 1 1 calc R U . . .
C2 C 0.3676(2) -0.29192(16) 0.59404(15) 0.0460(5) Uani 1 1 d . . . . .
H2 H 0.359807 -0.330933 0.657674 0.055 Uiso 1 1 calc R U . . .
C3 C 0.3988(2) -0.35417(16) 0.52109(16) 0.0465(5) Uani 1 1 d . . . . .
H3 H 0.412868 -0.434151 0.536137 0.056 Uiso 1 1 calc R U . . .
C4 C 0.4083(2) -0.29693(16) 0.42800(15) 0.0421(4) Uani 1 1 d . . . . .
H4 H 0.427925 -0.338330 0.379302 0.050 Uiso 1 1 calc R U . . .
C5 C 0.38883(17) -0.17492(14) 0.40372(13) 0.0323(4) Uani 1 1 d . . . . .
C6 C 0.35952(16) -0.11082(14) 0.47778(12) 0.0287(3) Uani 1 1 d . . . . .
C7 C 0.34125(16) 0.01413(14) 0.45256(12) 0.0277(3) Uani 1 1 d . . . . .
C8 C 0.35423(17) 0.06868(14) 0.35496(12) 0.0292(3) Uani 1 1 d . . . . .
C9 C 0.38201(19) 0.00059(15) 0.28369(13) 0.0365(4) Uani 1 1 d . . . . .
H9 H 0.388473 0.036969 0.219092 0.044 Uiso 1 1 calc R U . . .
C10 C 0.39938(19) -0.11597(16) 0.30713(13) 0.0373(4) Uani 1 1 d . . . . .
H10 H 0.418575 -0.157581 0.258558 0.045 Uiso 1 1 calc R U . . .
C11 C 0.31729(16) 0.07605(14) 0.52965(12) 0.0299(3) Uani 1 1 d . . . . .
H11 H 0.326162 0.032361 0.592880 0.036 Uiso 1 1 calc R U . . .
C12 C 0.26485(17) 0.23973(15) 0.59845(12) 0.0326(4) Uani 1 1 d . . . . .
C13 C 0.23958(18) 0.35950(15) 0.57546(13) 0.0354(4) Uani 1 1 d . . . . .
C14 C 0.2306(2) 0.41739(17) 0.65599(15) 0.0480(5) Uani 1 1 d . . . . .
C15 C 0.2653(2) 0.17523(16) 0.69489(14) 0.0395(4) Uani 1 1 d . . . . .
C16 C 0.0096(3) 0.3011(3) 0.2689(2) 0.0857(9) Uani 1 1 d . . . . .
H16A H 0.057283 0.226956 0.259981 0.129 Uiso 1 1 calc R U . . .
H16B H 0.025727 0.359726 0.215053 0.129 Uiso 1 1 calc R U . . .
H16C H -0.084561 0.302762 0.272623 0.129 Uiso 1 1 calc R U . . .
C17 C 0.28374(18) 0.51228(14) 0.22708(12) 0.0338(4) Uani 1 1 d . . . . .
C18 C 0.1603(2) 0.57833(17) 0.25023(15) 0.0454(5) Uani 1 1 d . . . . .
H18 H 0.101490 0.541911 0.290209 0.055 Uiso 1 1 calc R U . . .
C19 C 0.1258(2) 0.69403(17) 0.21525(16) 0.0500(5) Uani 1 1 d . . . . .
H19 H 0.042487 0.734855 0.230011 0.060 Uiso 1 1 calc R U . . .
C20 C 0.2131(2) 0.75341(16) 0.15731(14) 0.0458(5) Uani 1 1 d . . . . .
C21 C 0.1763(3) 0.87475(18) 0.12068(17) 0.0612(7) Uani 1 1 d . . . . .
H21 H 0.091935 0.915050 0.133967 0.073 Uiso 1 1 calc R U . . .
C22 C 0.2610(3) 0.93220(18) 0.06733(18) 0.0729(8) Uani 1 1 d . . . . .
H22 H 0.235454 1.011538 0.044348 0.088 Uiso 1 1 calc R U . . .
C23 C 0.3865(3) 0.87275(19) 0.04670(16) 0.0690(8) Uani 1 1 d . . . . .
H23 H 0.445619 0.912989 0.010870 0.083 Uiso 1 1 calc R U . . .
C24 C 0.4253(3) 0.75474(17) 0.07852(15) 0.0544(6) Uani 1 1 d . . . . .
H24 H 0.509411 0.716408 0.062771 0.065 Uiso 1 1 calc R U . . .
C25 C 0.3392(2) 0.69151(14) 0.13451(12) 0.0383(4) Uani 1 1 d . . . . .
C26 C 0.37416(18) 0.56642(14) 0.16852(12) 0.0326(4) Uani 1 1 d . . . . .
C27 C 0.50063(19) 0.50417(15) 0.14112(12) 0.0348(4) Uani 1 1 d . . . . .
H27 H 0.562550 0.546977 0.113821 0.042 Uiso 1 1 calc R U . . .
C28 C 0.66228(18) 0.33874(15) 0.12634(13) 0.0339(4) Uani 1 1 d . . . . .
C29 C 0.68934(18) 0.21941(15) 0.14881(12) 0.0345(4) Uani 1 1 d . . . . .
C30 C 0.8241(2) 0.15964(17) 0.13084(15) 0.0440(5) Uani 1 1 d . . . . .
C31 C 0.7567(2) 0.40105(17) 0.07874(14) 0.0416(4) Uani 1 1 d . . . . .
C32 C 0.2177(2) 0.27815(17) 0.03497(14) 0.0422(4) Uani 1 1 d . . . . .
C33 C 0.1224(2) 0.2903(2) -0.04257(17) 0.0614(6) Uani 1 1 d . . . . .
H33A H 0.169208 0.286676 -0.102220 0.092 Uiso 1 1 calc R U . . .
H33B H 0.059864 0.363113 -0.049693 0.092 Uiso 1 1 calc R U . . .
H33C H 0.074960 0.229042 -0.027048 0.092 Uiso 1 1 calc R U . . .
N11 N 0.0539(4) 0.7708(6) 0.4752(3) 0.219(3) Uani 1 1 d . . . . .
C34 C 0.0439(4) 0.8522(7) 0.4219(3) 0.153(3) Uani 1 1 d . . . . .
C35 C 0.0306(4) 0.9557(5) 0.3549(3) 0.1432(18) Uani 1 1 d . . . . .
H35A H 0.101977 0.949774 0.309227 0.215 Uiso 1 1 calc R U . . .
H35B H 0.034549 1.016041 0.387912 0.215 Uiso 1 1 calc R U . . .
H35C H -0.053799 0.973196 0.321192 0.215 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
Zn1 N6 2.0058(15) . ?
Zn1 O2 2.0413(11) . ?
Zn1 O1 2.0475(12) . ?
Zn1 N10 2.0885(17) . ?
Zn1 N7 2.1130(14) . ?
Zn2 N2 2.0016(16) . ?
Zn2 O1 2.0090(12) . ?
Zn2 O2 2.0464(11) . ?
Zn2 O3 2.0582(14) . ?
Zn2 N1 2.1012(14) . ?
O1 C17 1.337(2) . ?
O2 C8 1.3300(19) . ?
O3 C16 1.412(3) . ?
O3 H3A 0.9090 . ?
N1 C11 1.297(2) . ?
N1 C12 1.396(2) . ?
N2 C13 1.322(2) . ?
N2 H2A 0.7818 . ?
N3 C15 1.145(2) . ?
N4 C14 1.134(3) . ?
N6 C29 1.329(2) . ?
N6 H6A 0.7480 . ?
N7 C27 1.297(2) . ?
N7 C28 1.393(2) . ?
N8 C31 1.145(3) . ?
N9 C30 1.132(3) . ?
N10 C32 1.131(2) . ?
C1 C2 1.373(3) . ?
C1 C6 1.412(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.396(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.358(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.420(2) . ?
C4 H4 0.9300 . ?
C5 C10 1.408(2) . ?
C5 C6 1.423(2) . ?
C6 C7 1.456(2) . ?
C7 C8 1.409(2) . ?
C7 C11 1.440(2) . ?
C8 C9 1.422(2) . ?
C9 C10 1.358(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.390(2) . ?
C12 C15 1.415(3) . ?
C13 C14 1.454(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C26 1.399(2) . ?
C17 C18 1.411(2) . ?
C18 C19 1.358(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.404(3) . ?
C19 H19 0.9300 . ?
C20 C25 1.410(3) . ?
C20 C21 1.424(3) . ?
C21 C22 1.343(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.385(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.380(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.409(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.460(2) . ?
C26 C27 1.437(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.385(2) . ?
C28 C31 1.422(3) . ?
C29 C30 1.454(3) . ?
C32 C33 1.453(3) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
N11 C34 1.093(8) . ?
C34 C35 1.384(7) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?

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
N6 Zn1 O2 104.98(5) . . ?
N6 Zn1 O1 151.72(6) . . ?
O2 Zn1 O1 76.92(5) . . ?
N6 Zn1 N10 107.51(6) . . ?
O2 Zn1 N10 102.23(6) . . ?
O1 Zn1 N10 99.41(6) . . ?
N6 Zn1 N7 81.11(6) . . ?
O2 Zn1 N7 146.40(5) . . ?
O1 Zn1 N7 82.79(5) . . ?
N10 Zn1 N7 107.35(6) . . ?
N2 Zn2 O1 108.08(6) . . ?
N2 Zn2 O2 156.51(6) . . ?
O1 Zn2 O2 77.67(5) . . ?
N2 Zn2 O3 102.30(7) . . ?
O1 Zn2 O3 100.39(6) . . ?
O2 Zn2 O3 98.86(6) . . ?
N2 Zn2 N1 81.23(6) . . ?
O1 Zn2 N1 152.51(5) . . ?
O2 Zn2 N1 84.28(5) . . ?
O3 Zn2 N1 102.76(6) . . ?
C17 O1 Zn2 127.74(11) . . ?
C17 O1 Zn1 129.46(11) . . ?
Zn2 O1 Zn1 102.78(5) . . ?
C8 O2 Zn1 127.35(10) . . ?
C8 O2 Zn2 130.79(10) . . ?
Zn1 O2 Zn2 101.69(5) . . ?
C16 O3 Zn2 125.17(15) . . ?
C16 O3 H3A 114.9 . . ?
Zn2 O3 H3A 116.5 . . ?
C11 N1 C12 121.88(15) . . ?
C11 N1 Zn2 128.53(11) . . ?
C12 N1 Zn2 109.59(11) . . ?
C13 N2 Zn2 112.56(12) . . ?
C13 N2 H2A 114.9 . . ?
Zn2 N2 H2A 132.4 . . ?
C29 N6 Zn1 112.35(11) . . ?
C29 N6 H6A 116.3 . . ?
Zn1 N6 H6A 131.0 . . ?
C27 N7 C28 121.87(15) . . ?
C27 N7 Zn1 128.68(12) . . ?
C28 N7 Zn1 109.44(10) . . ?
C32 N10 Zn1 174.05(17) . . ?
C2 C1 C6 121.66(17) . . ?
C2 C1 H1 119.2 . . ?
C6 C1 H1 119.2 . . ?
C1 C2 C3 120.94(18) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 119.45(18) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 121.14(18) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C10 C5 C4 120.94(17) . . ?
C10 C5 C6 119.19(15) . . ?
C4 C5 C6 119.87(16) . . ?
C1 C6 C5 116.93(15) . . ?
C1 C6 C7 123.48(15) . . ?
C5 C6 C7 119.59(15) . . ?
C8 C7 C11 122.77(15) . . ?
C8 C7 C6 118.91(15) . . ?
C11 C7 C6 118.25(14) . . ?
O2 C8 C7 122.98(15) . . ?
O2 C8 C9 117.85(15) . . ?
C7 C8 C9 119.17(15) . . ?
C10 C9 C8 121.97(16) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C5 121.16(16) . . ?
C9 C10 H10 119.4 . . ?
C5 C10 H10 119.4 . . ?
N1 C11 C7 125.97(15) . . ?
N1 C11 H11 117.0 . . ?
C7 C11 H11 117.0 . . ?
C13 C12 N1 115.14(15) . . ?
C13 C12 C15 122.77(16) . . ?
N1 C12 C15 122.03(15) . . ?
N2 C13 C12 121.18(16) . . ?
N2 C13 C14 121.74(17) . . ?
C12 C13 C14 117.00(17) . . ?
N4 C14 C13 177.2(3) . . ?
N3 C15 C12 175.8(2) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 C26 122.29(15) . . ?
O1 C17 C18 117.82(16) . . ?
C26 C17 C18 119.88(16) . . ?
C19 C18 C17 121.3(2) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 121.5(2) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C25 119.32(17) . . ?
C19 C20 C21 121.2(2) . . ?
C25 C20 C21 119.4(2) . . ?
C22 C21 C20 121.3(2) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C23 119.7(2) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 121.0(2) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 120.9(2) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C24 C25 C20 117.54(17) . . ?
C24 C25 C26 123.16(18) . . ?
C20 C25 C26 119.30(18) . . ?
C17 C26 C27 122.74(15) . . ?
C17 C26 C25 118.69(16) . . ?
C27 C26 C25 118.57(16) . . ?
N7 C27 C26 125.34(16) . . ?
N7 C27 H27 117.3 . . ?
C26 C27 H27 117.3 . . ?
C29 C28 N7 115.48(15) . . ?
C29 C28 C31 121.99(17) . . ?
N7 C28 C31 122.50(16) . . ?
N6 C29 C28 121.37(16) . . ?
N6 C29 C30 121.54(16) . . ?
C28 C29 C30 117.04(17) . . ?
N9 C30 C29 176.1(2) . . ?
N8 C31 C28 177.9(2) . . ?
N10 C32 C33 179.5(2) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N11 C34 C35 179.6(7) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?

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
N6 H6A N3 0.75 2.59 3.324(2) 166.7 2_656 yes
O3 H3A N11 0.91 1.88 2.719(4) 152.1 2_566 yes
N6 H6A N3 0.75 2.59 3.324(2) 166.7 2_656 yes
O3 H3A N11 0.91 1.88 2.719(4) 152.1 2_566 yes
N6 H6A N3 0.75 2.59 3.324(2) 166.7 2_656 yes
O3 H3A N11 0.91 1.88 2.719(4) 152.1 2_566 yes
N6 H6A N3 0.75 2.59 3.324(2) 166.7 2_656 yes
N6 H6A N3 0.75 2.59 3.324(2) 166.7 2_656 yes
O3 H3A N11 0.91 1.88 2.719(4) 152.1 2_566 yes
N6 H6A N3 0.75 2.59 3.324(2) 166.7 2_656 yes
O3 H3A N11 0.91 1.88 2.719(4) 152.1 2_566 yes
N6 H6A N3 0.75 2.59 3.324(2) 166.7 2_656 yes

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_ZnL5c-o
_database_code_depnum_ccdc_archive 'CCDC 1915782'
_audit_update_record             
;
2020-02-02 deposited with the CCDC.	2020-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H13 Cl N4 O3 Zn'
_chemical_formula_weight         482.18

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'
Cl Cl 0.1484 0.1585 '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'
Zn Zn 0.2839 1.4301 '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                   6.0468(7)
_cell_length_b                   31.046(3)
_cell_length_c                   10.7876(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.317(4)
_cell_angle_gamma                90
_cell_volume                     1992.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4158
_cell_measurement_theta_min      1.953
_cell_measurement_theta_max      25.481

_exptl_crystal_description       rodlike
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    1.400
_shelx_estimated_absorpt_T_min   0.663
_shelx_estimated_absorpt_T_max   0.730
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18611
_diffrn_reflns_av_unetI/netI     0.0838
_diffrn_reflns_av_R_equivalents  0.1018
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.028
_diffrn_reflns_theta_max         24.888
_diffrn_reflns_theta_full        24.888
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3430
_reflns_number_gt                2127
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0459P)²+1.3816P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3430
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1217
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
Zn01 Zn 0.82233(10) 0.46356(2) 0.33895(6) 0.0394(2) Uani 1 1 d . . . . .
Cl1 Cl 1.0183(3) 0.67363(6) 0.16812(19) 0.0863(6) Uani 1 1 d . . . . .
O2 O 1.1104(5) 0.43678(11) 0.4171(3) 0.0408(9) Uani 1 1 d . . . . .
O1 O 0.9475(5) 0.51950(11) 0.2986(3) 0.0422(9) Uani 1 1 d . . . . .
O3 O 0.7175(5) 0.47997(11) 0.5064(3) 0.0404(9) Uani 1 1 d . . . . .
H3B H 0.723917 0.507452 0.516279 0.048 Uiso 1 1 d R U . . .
H3A H 0.840281 0.476539 0.578802 0.048 Uiso 1 1 d R U . . .
N4 N 0.6946(7) 0.40265(13) 0.3059(4) 0.0366(10) Uani 1 1 d . . . . .
N1 N 0.5311(6) 0.47723(14) 0.2101(4) 0.0362(11) Uani 1 1 d . . . . .
C14 C 1.1520(8) 0.39800(17) 0.4580(5) 0.0365(13) Uani 1 1 d . . . . .
C13 C 0.9967(9) 0.36275(16) 0.4347(5) 0.0386(13) Uani 1 1 d . . . . .
N2 N 0.2502(9) 0.33285(18) 0.1932(5) 0.0693(16) Uani 1 1 d . . . . .
C1 C 0.8422(9) 0.55247(17) 0.2396(5) 0.0386(13) Uani 1 1 d . . . . .
C6 C 0.6133(8) 0.55220(17) 0.1752(5) 0.0385(13) Uani 1 1 d . . . . .
C12 C 0.7849(8) 0.36691(18) 0.3571(5) 0.0410(14) Uani 1 1 d . . . . .
H12 H 0.700236 0.341889 0.340303 0.049 Uiso 1 1 calc R U . . .
C7 C 0.4725(9) 0.51476(18) 0.1621(5) 0.0399(13) Uani 1 1 d . . . . .
H7 H 0.328129 0.517549 0.115544 0.048 Uiso 1 1 calc R U . . .
C15 C 1.3709(9) 0.38975(18) 0.5284(5) 0.0452(14) Uani 1 1 d . . . . .
H15 H 1.472814 0.412377 0.544263 0.054 Uiso 1 1 calc R U . . .
C11 C 0.4801(8) 0.40270(17) 0.2335(5) 0.0369(13) Uani 1 1 d . . . . .
C8 C 0.3969(8) 0.44091(18) 0.1864(5) 0.0380(13) Uani 1 1 d . . . . .
C5 C 0.5165(10) 0.59058(18) 0.1167(5) 0.0473(15) Uani 1 1 d . . . . .
H5 H 0.366586 0.590293 0.077219 0.057 Uiso 1 1 calc R U . . .
C22 C 1.0655(9) 0.32000(17) 0.4888(5) 0.0457(14) Uani 1 1 d . . . . .
C9 C 0.1691(9) 0.44425(18) 0.1179(5) 0.0436(14) Uani 1 1 d . . . . .
N3 N -0.0130(8) 0.44808(17) 0.0665(5) 0.0658(15) Uani 1 1 d . . . . .
C2 C 0.9640(10) 0.59121(18) 0.2357(5) 0.0494(15) Uani 1 1 d . . . . .
H2 H 1.114516 0.592507 0.273850 0.059 Uiso 1 1 calc R U . . .
C17 C 1.2870(10) 0.31439(19) 0.5567(6) 0.0548(16) Uani 1 1 d . . . . .
C10 C 0.3506(10) 0.36369(19) 0.2111(5) 0.0464(15) Uani 1 1 d . . . . .
C16 C 1.4351(10) 0.35012(19) 0.5728(5) 0.0523(16) Uani 1 1 d . . . . .
H16 H 1.581607 0.346183 0.615454 0.063 Uiso 1 1 calc R U . . .
C4 C 0.6363(10) 0.6276(2) 0.1168(6) 0.0591(17) Uani 1 1 d . . . . .
H4 H 0.570486 0.652471 0.078848 0.071 Uiso 1 1 calc R U . . .
C3 C 0.8608(10) 0.62706(18) 0.1756(6) 0.0530(16) Uani 1 1 d . . . . .
C21 C 0.9215(11) 0.28436(19) 0.4790(7) 0.070(2) Uani 1 1 d . . . . .
H21 H 0.773830 0.287340 0.437195 0.084 Uiso 1 1 calc R U . . .
C18 C 1.3577(12) 0.2736(2) 0.6075(7) 0.074(2) Uani 1 1 d . . . . .
H18 H 1.503572 0.269991 0.651407 0.089 Uiso 1 1 calc R U . . .
C19 C 1.2129(13) 0.2393(2) 0.5925(8) 0.094(3) Uani 1 1 d . . . . .
H19 H 1.260817 0.212385 0.624023 0.113 Uiso 1 1 calc R U . . .
C20 C 0.9927(13) 0.2453(2) 0.5295(7) 0.091(3) Uani 1 1 d . . . . .
H20 H 0.892664 0.222279 0.521627 0.110 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
Zn01 O1 1.974(3) . ?
Zn01 O2 1.977(3) . ?
Zn01 N4 2.050(4) . ?
Zn01 N1 2.083(4) . ?
Zn01 O3 2.082(3) . ?
Cl1 C3 1.741(6) . ?
O2 C14 1.292(6) . ?
O1 C1 1.309(6) . ?
O3 H3B 0.8600 . ?
O3 H3A 0.9824 . ?
N4 C12 1.314(6) . ?
N4 C11 1.389(6) . ?
N1 C7 1.298(6) . ?
N1 C8 1.386(6) . ?
C14 C15 1.426(7) . ?
C14 C13 1.435(7) . ?
C13 C12 1.405(7) . ?
C13 C22 1.479(7) . ?
N2 C10 1.131(6) . ?
C1 C2 1.415(7) . ?
C1 C6 1.433(7) . ?
C6 C5 1.424(7) . ?
C6 C7 1.433(7) . ?
C12 H12 0.9300 . ?
C7 H7 0.9300 . ?
C15 C16 1.352(7) . ?
C15 H15 0.9300 . ?
C11 C8 1.352(7) . ?
C11 C10 1.439(7) . ?
C8 C9 1.446(7) . ?
C5 C4 1.358(7) . ?
C5 H5 0.9300 . ?
C22 C21 1.400(7) . ?
C22 C17 1.418(8) . ?
C9 N3 1.147(6) . ?
C2 C3 1.380(7) . ?
C2 H2 0.9300 . ?
C17 C16 1.417(7) . ?
C17 C18 1.416(8) . ?
C16 H16 0.9300 . ?
C4 C3 1.392(8) . ?
C4 H4 0.9300 . ?
C21 C20 1.367(8) . ?
C21 H21 0.9300 . ?
C18 C19 1.368(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.395(9) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn01 O2 96.93(14) . . ?
O1 Zn01 N4 157.03(15) . . ?
O2 Zn01 N4 87.83(15) . . ?
O1 Zn01 N1 89.15(15) . . ?
O2 Zn01 N1 160.96(15) . . ?
N4 Zn01 N1 79.90(16) . . ?
O1 Zn01 O3 99.47(14) . . ?
O2 Zn01 O3 96.61(14) . . ?
N4 Zn01 O3 102.29(14) . . ?
N1 Zn01 O3 100.18(14) . . ?
C14 O2 Zn01 129.8(3) . . ?
C1 O1 Zn01 128.5(3) . . ?
Zn01 O3 H3B 109.7 . . ?
Zn01 O3 H3A 111.1 . . ?
H3B O3 H3A 89.9 . . ?
C12 N4 C11 120.9(5) . . ?
C12 N4 Zn01 126.2(4) . . ?
C11 N4 Zn01 112.4(3) . . ?
C7 N1 C8 123.2(5) . . ?
C7 N1 Zn01 125.9(4) . . ?
C8 N1 Zn01 110.7(3) . . ?
O2 C14 C15 117.1(5) . . ?
O2 C14 C13 124.7(5) . . ?
C15 C14 C13 118.2(5) . . ?
C12 C13 C14 122.2(5) . . ?
C12 C13 C22 118.6(5) . . ?
C14 C13 C22 119.1(5) . . ?
O1 C1 C2 117.9(5) . . ?
O1 C1 C6 125.1(5) . . ?
C2 C1 C6 117.0(5) . . ?
C5 C6 C1 119.6(5) . . ?
C5 C6 C7 116.4(5) . . ?
C1 C6 C7 123.9(5) . . ?
N4 C12 C13 126.4(5) . . ?
N4 C12 H12 116.8 . . ?
C13 C12 H12 116.8 . . ?
N1 C7 C6 125.0(5) . . ?
N1 C7 H7 117.5 . . ?
C6 C7 H7 117.5 . . ?
C16 C15 C14 122.2(5) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C8 C11 N4 117.3(5) . . ?
C8 C11 C10 121.4(5) . . ?
N4 C11 C10 121.3(5) . . ?
C11 C8 N1 118.6(5) . . ?
C11 C8 C9 120.8(5) . . ?
N1 C8 C9 120.6(5) . . ?
C4 C5 C6 122.0(5) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C21 C22 C17 117.3(5) . . ?
C21 C22 C13 123.5(5) . . ?
C17 C22 C13 119.1(5) . . ?
N3 C9 C8 177.5(6) . . ?
C3 C2 C1 120.4(5) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C16 C17 C22 119.0(5) . . ?
C16 C17 C18 120.9(6) . . ?
C22 C17 C18 120.1(6) . . ?
N2 C10 C11 179.4(7) . . ?
C15 C16 C17 122.3(6) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C5 C4 C3 117.9(6) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C2 C3 C4 123.1(5) . . ?
C2 C3 Cl1 119.1(5) . . ?
C4 C3 Cl1 117.8(5) . . ?
C20 C21 C22 121.6(6) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C19 C18 C17 120.5(7) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 119.4(7) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 121.1(7) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?

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
Zn01 O2 C14 C15 -170.1(3) . . . . ?
Zn01 O2 C14 C13 11.7(7) . . . . ?
O2 C14 C13 C12 3.9(8) . . . . ?
C15 C14 C13 C12 -174.3(5) . . . . ?
O2 C14 C13 C22 -179.2(5) . . . . ?
C15 C14 C13 C22 2.7(7) . . . . ?
Zn01 O1 C1 C2 172.2(4) . . . . ?
Zn01 O1 C1 C6 -9.6(7) . . . . ?
O1 C1 C6 C5 178.7(5) . . . . ?
C2 C1 C6 C5 -3.1(7) . . . . ?
O1 C1 C6 C7 -3.1(8) . . . . ?
C2 C1 C6 C7 175.1(5) . . . . ?
C11 N4 C12 C13 -178.2(5) . . . . ?
Zn01 N4 C12 C13 -6.7(7) . . . . ?
C14 C13 C12 N4 -6.0(8) . . . . ?
C22 C13 C12 N4 177.1(5) . . . . ?
C8 N1 C7 C6 -174.4(5) . . . . ?
Zn01 N1 C7 C6 9.5(7) . . . . ?
C5 C6 C7 N1 -179.1(5) . . . . ?
C1 C6 C7 N1 2.6(8) . . . . ?
O2 C14 C15 C16 -178.1(5) . . . . ?
C13 C14 C15 C16 0.2(8) . . . . ?
C12 N4 C11 C8 178.5(5) . . . . ?
Zn01 N4 C11 C8 6.0(6) . . . . ?
C12 N4 C11 C10 -0.6(7) . . . . ?
Zn01 N4 C11 C10 -173.1(4) . . . . ?
N4 C11 C8 N1 1.6(7) . . . . ?
C10 C11 C8 N1 -179.3(5) . . . . ?
N4 C11 C8 C9 -175.5(4) . . . . ?
C10 C11 C8 C9 3.6(8) . . . . ?
C7 N1 C8 C11 175.2(5) . . . . ?
Zn01 N1 C8 C11 -8.2(6) . . . . ?
C7 N1 C8 C9 -7.7(7) . . . . ?
Zn01 N1 C8 C9 168.9(4) . . . . ?
C1 C6 C5 C4 1.8(8) . . . . ?
C7 C6 C5 C4 -176.5(5) . . . . ?
C12 C13 C22 C21 -7.6(8) . . . . ?
C14 C13 C22 C21 175.4(5) . . . . ?
C12 C13 C22 C17 173.7(5) . . . . ?
C14 C13 C22 C17 -3.3(8) . . . . ?
O1 C1 C2 C3 -179.5(5) . . . . ?
C6 C1 C2 C3 2.1(8) . . . . ?
C21 C22 C17 C16 -177.6(6) . . . . ?
C13 C22 C17 C16 1.2(8) . . . . ?
C21 C22 C17 C18 2.3(9) . . . . ?
C13 C22 C17 C18 -178.9(6) . . . . ?
C14 C15 C16 C17 -2.4(9) . . . . ?
C22 C17 C16 C15 1.7(9) . . . . ?
C18 C17 C16 C15 -178.2(6) . . . . ?
C6 C5 C4 C3 0.5(9) . . . . ?
C1 C2 C3 C4 0.2(9) . . . . ?
C1 C2 C3 Cl1 -177.9(4) . . . . ?
C5 C4 C3 C2 -1.6(10) . . . . ?
C5 C4 C3 Cl1 176.5(5) . . . . ?
C17 C22 C21 C20 -1.9(10) . . . . ?
C13 C22 C21 C20 179.4(6) . . . . ?
C16 C17 C18 C19 179.4(7) . . . . ?
C22 C17 C18 C19 -0.5(11) . . . . ?
C17 C18 C19 C20 -1.7(12) . . . . ?
C22 C21 C20 C19 -0.3(12) . . . . ?
C18 C19 C20 C21 2.1(13) . . . . ?

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
C15 H15 O3 0.93 2.64 3.532(6) 160.5 1_655 yes
C7 H7 N3 0.93 2.70 3.561(7) 154.4 3_565 yes
O3 H3A O1 0.98 1.67 2.647(4) 169.5 3_766 yes
O3 H3B O2 0.86 2.06 2.853(5) 152.1 3_766 yes
C15 H15 O3 0.93 2.64 3.532(6) 160.5 1_655 yes
C7 H7 N3 0.93 2.70 3.561(7) 154.4 3_565 yes
O3 H3A O1 0.98 1.67 2.647(4) 169.5 3_766 yes
O3 H3B O2 0.86 2.06 2.853(5) 152.1 3_766 yes

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.076

