# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_HL1
_database_code_depnum_ccdc_archive 'CCDC 1938874'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2019-07-06 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;
_audit_creation_date             2019-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H8 N2'
_chemical_formula_sum            'C11 H8 N2'
_chemical_formula_weight         168.19
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.2981(3)
_cell_length_b                   11.7510(6)
_cell_length_c                   13.3334(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     830.11(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5406
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.25
_cell_measurement_theta_min      3.47
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0653 before and 0.0564 after correction. The Ratio of minimum to maximum transmission is 0.8936. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21054
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.663
_diffrn_reflns_theta_min         3.056
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2030
_reflns_number_total             2572
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 709 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2572
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0457
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0414P)²+0.1777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.1023
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N2-H2
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.3183(3) 0.65233(16) 0.45916(13) 0.0243(4) Uani 1 1 d D . . . .
N1 N 0.1186(3) 0.64196(16) 0.52350(13) 0.0268(4) Uani 1 1 d . . . . .
C1 C 0.0590(4) 0.53225(18) 0.52431(16) 0.0268(4) Uani 1 1 d . . . . .
H1 H -0.076040 0.500442 0.561896 0.032 Uiso 1 1 calc R . . . .
C2 C 0.2231(4) 0.46885(17) 0.46178(15) 0.0234(4) Uani 1 1 d . . . . .
C3 C 0.3865(4) 0.54952(16) 0.42108(14) 0.0209(4) Uani 1 1 d . . . . .
C4 C 0.5791(4) 0.52158(17) 0.34994(14) 0.0219(4) Uani 1 1 d . . . . .
C5 C 0.7446(4) 0.60085(19) 0.30575(16) 0.0272(4) Uani 1 1 d . . . . .
H5 H 0.734407 0.678960 0.323674 0.033 Uiso 1 1 calc R . . . .
C6 C 0.9207(4) 0.5656(2) 0.23680(17) 0.0332(5) Uani 1 1 d . . . . .
H6 H 1.031020 0.619587 0.206921 0.040 Uiso 1 1 calc R . . . .
C7 C 0.9387(4) 0.4504(2) 0.21027(16) 0.0337(5) Uani 1 1 d . . . . .
H7 H 1.061950 0.426619 0.162945 0.040 Uiso 1 1 calc R . . . .
C8 C 0.7790(4) 0.3719(2) 0.25241(16) 0.0306(5) Uani 1 1 d . . . . .
H8 H 0.792054 0.294244 0.233294 0.037 Uiso 1 1 calc R . . . .
C9 C 0.5958(4) 0.40441(18) 0.32361(14) 0.0241(4) Uani 1 1 d . . . . .
C10 C 0.4293(5) 0.32270(17) 0.36818(16) 0.0283(5) Uani 1 1 d . . . . .
H10 H 0.447440 0.244813 0.350520 0.034 Uiso 1 1 calc R . . . .
C11 C 0.2462(4) 0.35227(18) 0.43479(16) 0.0283(5) Uani 1 1 d . . . . .
H11 H 0.136712 0.296516 0.462535 0.034 Uiso 1 1 calc R . . . .
H2 H 0.400(5) 0.7197(18) 0.4546(18) 0.034 Uiso 1 1 d DR . . . .


_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
N2 N1 1.367(2) . ?
N2 C3 1.359(3) . ?
N2 H2 0.905(19) . ?
N1 C1 1.327(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.416(3) . ?
C2 C3 1.394(3) . ?
C2 C11 1.422(3) . ?
C3 C4 1.431(3) . ?
C4 C5 1.408(3) . ?
C4 C9 1.424(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.374(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.402(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.372(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.410(3) . ?
C9 C10 1.433(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.360(3) . ?
C11 H11 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N2 H2 119.4(16) . . ?
C3 N2 N1 111.15(17) . . ?
C3 N2 H2 128.7(16) . . ?
C1 N1 N2 106.02(17) . . ?
N1 C1 H1 124.5 . . ?
N1 C1 C2 111.09(19) . . ?
C2 C1 H1 124.5 . . ?
C1 C2 C11 135.1(2) . . ?
C3 C2 C1 104.64(18) . . ?
C3 C2 C11 120.21(19) . . ?
N2 C3 C2 107.08(18) . . ?
N2 C3 C4 129.86(18) . . ?
C2 C3 C4 123.02(18) . . ?
C5 C4 C3 124.70(19) . . ?
C5 C4 C9 119.87(19) . . ?
C9 C4 C3 115.43(18) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.2(2) . . ?
C9 C8 H8 119.4 . . ?
C4 C9 C10 120.51(19) . . ?
C8 C9 C4 118.1(2) . . ?
C8 C9 C10 121.4(2) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 C9 122.59(19) . . ?
C11 C10 H10 118.7 . . ?
C2 C11 H11 120.9 . . ?
C10 C11 C2 118.22(19) . . ?
C10 C11 H11 120.9 . . ?

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
N2 H2 N1 0.905(19) 2.02(2) 2.903(3) 166(2) 4_566 yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1938876'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2019-07-06 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;
_audit_creation_date             2019-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H32 Cu N10 O6'
_chemical_formula_sum            'C44 H32 Cu N10 O6'
_chemical_formula_weight         860.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.0209(3)
_cell_length_b                   21.4464(6)
_cell_length_c                   11.1543(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.1810(10)
_cell_angle_gamma                90
_cell_volume                     1899.23(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8775
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.64
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.779
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0571 before and 0.0520 after correction. The Ratio of minimum to maximum transmission is 0.8949. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             886
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25442
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.635
_diffrn_reflns_theta_min         2.648
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4670
_reflns_number_total             5848
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         5848
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0352P)²+1.7178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0995
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N2-H2 = N4-H4
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4A), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.500000 0.500000 0.01046(7) Uani 1 2 d S T P . .
O1 O 0.23615(16) 0.47088(7) 0.54859(13) 0.0231(3) Uani 1 1 d . . . . .
O2 O 0.05153(17) 0.44064(7) 0.39784(13) 0.0220(3) Uani 1 1 d . . . . .
O3 O 0.02097(19) 0.41516(7) 0.57988(13) 0.0266(3) Uani 1 1 d . . . . .
N1 N 0.53857(18) 0.41621(7) 0.42230(13) 0.0140(3) Uani 1 1 d . . . . .
N2 N 0.69002(18) 0.38723(7) 0.42807(14) 0.0144(3) Uani 1 1 d D . . . .
N3 N 0.40471(17) 0.53506(7) 0.33828(13) 0.0129(3) Uani 1 1 d . . . . .
N4 N 0.24025(18) 0.52768(7) 0.29110(13) 0.0133(3) Uani 1 1 d D . . . .
N5 N 0.10413(18) 0.44176(7) 0.50947(14) 0.0153(3) Uani 1 1 d . . . . .
C1 C 0.4287(2) 0.38202(8) 0.34989(16) 0.0162(3) Uani 1 1 d . . . . .
H1 H 0.311862 0.390910 0.331026 0.019 Uiso 1 1 calc R . . . .
C2 C 0.5105(2) 0.33056(8) 0.30500(16) 0.0159(3) Uani 1 1 d . . . . .
C3 C 0.4592(2) 0.28220(9) 0.21964(18) 0.0210(4) Uani 1 1 d . . . . .
H3 H 0.344832 0.278158 0.184163 0.025 Uiso 1 1 calc R . . . .
C4 C 0.5780(3) 0.24227(9) 0.19064(18) 0.0216(4) Uani 1 1 d . . . . .
H4A H 0.546088 0.210862 0.131785 0.026 Uiso 1 1 calc R . . . .
C5 C 0.7514(2) 0.24592(8) 0.24624(17) 0.0175(3) Uani 1 1 d . . . . .
C6 C 0.8719(3) 0.20322(9) 0.21497(19) 0.0232(4) Uani 1 1 d . . . . .
H6 H 0.838897 0.172549 0.154818 0.028 Uiso 1 1 calc R . . . .
C7 C 1.0359(3) 0.20532(9) 0.2701(2) 0.0264(4) Uani 1 1 d . . . . .
H7 H 1.115533 0.176406 0.247374 0.032 Uiso 1 1 calc R . . . .
C8 C 1.0867(3) 0.24992(9) 0.3597(2) 0.0254(4) Uani 1 1 d . . . . .
H8 H 1.199824 0.250468 0.398962 0.031 Uiso 1 1 calc R . . . .
C9 C 0.9729(2) 0.29296(9) 0.39112(19) 0.0201(4) Uani 1 1 d . . . . .
H9 H 1.008022 0.323231 0.451646 0.024 Uiso 1 1 calc R . . . .
C10 C 0.8051(2) 0.29225(8) 0.33394(17) 0.0154(3) Uani 1 1 d . . . . .
C11 C 0.6781(2) 0.33562(8) 0.35769(16) 0.0141(3) Uani 1 1 d . . . . .
C12 C 0.4735(2) 0.57195(8) 0.26271(16) 0.0162(3) Uani 1 1 d . . . . .
H12 H 0.587881 0.585006 0.273562 0.019 Uiso 1 1 calc R . . . .
C13 C 0.3517(2) 0.58876(9) 0.16429(16) 0.0166(3) Uani 1 1 d . . . . .
C14 C 0.3506(3) 0.62667(10) 0.05911(18) 0.0234(4) Uani 1 1 d . . . . .
H14 H 0.449973 0.647020 0.042540 0.028 Uiso 1 1 calc R . . . .
C15 C 0.2032(3) 0.63282(10) -0.01666(18) 0.0253(4) Uani 1 1 d . . . . .
H15 H 0.201099 0.657940 -0.087004 0.030 Uiso 1 1 calc R . . . .
C16 C 0.0503(3) 0.60281(9) 0.00544(17) 0.0211(4) Uani 1 1 d . . . . .
C17 C -0.1022(3) 0.61037(11) -0.07449(18) 0.0278(5) Uani 1 1 d . . . . .
H17 H -0.103712 0.635511 -0.144750 0.033 Uiso 1 1 calc R . . . .
C18 C -0.2469(3) 0.58203(11) -0.05198(19) 0.0293(5) Uani 1 1 d . . . . .
H18 H -0.347789 0.587779 -0.106754 0.035 Uiso 1 1 calc R . . . .
C19 C -0.2489(2) 0.54465(10) 0.05058(18) 0.0246(4) Uani 1 1 d . . . . .
H19 H -0.350416 0.525113 0.065034 0.030 Uiso 1 1 calc R . . . .
C20 C -0.1032(2) 0.53624(9) 0.13058(17) 0.0193(4) Uani 1 1 d . . . . .
H20 H -0.104302 0.511047 0.200515 0.023 Uiso 1 1 calc R . . . .
C21 C 0.0468(2) 0.56487(9) 0.10876(16) 0.0166(3) Uani 1 1 d . . . . .
C22 C 0.2039(2) 0.55940(8) 0.18631(15) 0.0140(3) Uani 1 1 d . . . . .
H4 H 0.177(3) 0.5044(9) 0.3282(19) 0.017 Uiso 1 1 d DR . . . .
H2 H 0.779(2) 0.4040(10) 0.4613(19) 0.017 Uiso 1 1 d DR . . . .


_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
Cu1 O1 2.3429(13) . ?
Cu1 O1 2.3429(13) 3_666 ?
Cu1 N1 2.0377(15) . ?
Cu1 N1 2.0376(15) 3_666 ?
Cu1 N3 2.0027(14) 3_666 ?
Cu1 N3 2.0027(14) . ?
O1 N5 1.2531(19) . ?
O2 N5 1.257(2) . ?
O3 N5 1.240(2) . ?
N1 N2 1.358(2) . ?
N1 C1 1.328(2) . ?
N2 C11 1.352(2) . ?
N2 H2 0.841(15) . ?
N3 N4 1.3582(19) . ?
N3 C12 1.332(2) . ?
N4 C22 1.348(2) . ?
N4 H4 0.860(16) . ?
C1 H1 0.9500 . ?
C1 C2 1.412(2) . ?
C2 C3 1.428(2) . ?
C2 C11 1.392(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.354(3) . ?
C4 H4A 0.9500 . ?
C4 C5 1.442(3) . ?
C5 C6 1.411(3) . ?
C5 C10 1.418(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.371(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.402(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.378(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.405(3) . ?
C10 C11 1.432(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.409(2) . ?
C13 C14 1.426(3) . ?
C13 C22 1.395(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.358(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.437(3) . ?
C16 C17 1.416(3) . ?
C16 C21 1.414(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.365(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.399(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.377(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.402(3) . ?
C21 C22 1.428(2) . ?

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 Cu1 O1 180.0 3_666 . ?
N1 Cu1 O1 86.55(6) 3_666 . ?
N1 Cu1 O1 93.45(6) . . ?
N1 Cu1 O1 93.45(6) 3_666 3_666 ?
N1 Cu1 O1 86.55(6) . 3_666 ?
N1 Cu1 N1 180.0 3_666 . ?
N3 Cu1 O1 93.84(5) 3_666 3_666 ?
N3 Cu1 O1 86.16(5) 3_666 . ?
N3 Cu1 O1 93.84(5) . . ?
N3 Cu1 O1 86.16(5) . 3_666 ?
N3 Cu1 N1 90.54(6) 3_666 3_666 ?
N3 Cu1 N1 90.55(6) . . ?
N3 Cu1 N1 89.45(6) . 3_666 ?
N3 Cu1 N1 89.45(6) 3_666 . ?
N3 Cu1 N3 180.0 3_666 . ?
N5 O1 Cu1 143.00(12) . . ?
N2 N1 Cu1 124.92(11) . . ?
C1 N1 Cu1 128.15(12) . . ?
C1 N1 N2 106.73(14) . . ?
N1 N2 H2 121.7(15) . . ?
C11 N2 N1 110.98(14) . . ?
C11 N2 H2 126.4(15) . . ?
N4 N3 Cu1 122.03(11) . . ?
C12 N3 Cu1 130.82(12) . . ?
C12 N3 N4 106.93(14) . . ?
N3 N4 H4 119.4(15) . . ?
C22 N4 N3 110.84(14) . . ?
C22 N4 H4 129.8(15) . . ?
O1 N5 O2 120.16(15) . . ?
O3 N5 O1 120.86(16) . . ?
O3 N5 O2 118.94(15) . . ?
N1 C1 H1 124.9 . . ?
N1 C1 C2 110.22(16) . . ?
C2 C1 H1 124.9 . . ?
C1 C2 C3 134.41(17) . . ?
C11 C2 C1 105.00(15) . . ?
C11 C2 C3 120.47(17) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.22(18) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 H4A 119.0 . . ?
C3 C4 C5 122.09(17) . . ?
C5 C4 H4A 119.0 . . ?
C6 C5 C4 120.75(18) . . ?
C6 C5 C10 118.27(18) . . ?
C10 C5 C4 120.98(16) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.02(19) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.32(18) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.19(19) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.24(19) . . ?
C10 C9 H9 119.9 . . ?
C5 C10 C11 115.36(16) . . ?
C9 C10 C5 119.89(16) . . ?
C9 C10 C11 124.75(17) . . ?
N2 C11 C2 107.05(15) . . ?
N2 C11 C10 130.19(16) . . ?
C2 C11 C10 122.74(16) . . ?
N3 C12 H12 125.0 . . ?
N3 C12 C13 109.95(15) . . ?
C13 C12 H12 125.0 . . ?
C12 C13 C14 135.18(18) . . ?
C22 C13 C12 105.07(15) . . ?
C22 C13 C14 119.74(17) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 C13 118.06(19) . . ?
C15 C14 H14 121.0 . . ?
C14 C15 H15 118.7 . . ?
C14 C15 C16 122.56(18) . . ?
C16 C15 H15 118.7 . . ?
C17 C16 C15 121.48(18) . . ?
C21 C16 C15 120.91(17) . . ?
C21 C16 C17 117.61(19) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 120.93(19) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 120.95(19) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.8(2) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 119.99(19) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C22 115.03(17) . . ?
C20 C21 C16 120.67(17) . . ?
C20 C21 C22 124.30(17) . . ?
N4 C22 C13 107.21(15) . . ?
N4 C22 C21 129.08(16) . . ?
C13 C22 C21 123.71(16) . . ?

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
N4 H4 O2 0.860(16) 1.925(16) 2.776(2) 170(2) . yes
N2 H2 O3 0.841(15) 2.197(17) 2.999(2) 159(2) 1_655 yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1938879'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2019-07-06 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;
_audit_creation_date             2019-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 Cl2 N3 Zn'
_chemical_formula_sum            'C16 H11 Cl2 N3 Zn'
_chemical_formula_weight         381.55
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.7934(11)
_cell_length_b                   14.5059(17)
_cell_length_c                   12.1149(14)
_cell_angle_alpha                90
_cell_angle_beta                 105.893(4)
_cell_angle_gamma                90
_cell_volume                     1486.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1937
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.18
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.689
_exptl_absorpt_coefficient_mu    2.009
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0748 before and 0.0594 after correction. The Ratio of minimum to maximum transmission is 0.7947. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9706
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.471
_diffrn_reflns_theta_min         2.788
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2185
_reflns_number_total             3043
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.775
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3043
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0563P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1149
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12),
 C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.61763(6) 0.70711(3) 0.50109(4) 0.01603(16) Uani 1 1 d . . . . .
Cl1 Cl 0.39528(13) 0.75138(7) 0.37772(10) 0.0231(3) Uani 1 1 d . . . . .
Cl2 Cl 0.80881(13) 0.81020(7) 0.54368(9) 0.0223(3) Uani 1 1 d . . . . .
N3 N 0.5856(4) 0.6439(2) 0.6458(3) 0.0167(8) Uani 1 1 d . . . . .
N2 N 0.7043(4) 0.5232(2) 0.5774(3) 0.0164(8) Uani 1 1 d . . . . .
N1 N 0.6922(4) 0.5748(2) 0.4789(3) 0.0156(8) Uani 1 1 d . . . . .
C1 C 0.5190(5) 0.6803(3) 0.7237(4) 0.0245(10) Uani 1 1 d . . . . .
H1 H 0.481220 0.741913 0.713256 0.029 Uiso 1 1 calc R . . . .
C2 C 0.5035(6) 0.6322(4) 0.8172(4) 0.0269(11) Uani 1 1 d . . . . .
H2 H 0.454632 0.659848 0.869820 0.032 Uiso 1 1 calc R . . . .
C3 C 0.5600(6) 0.5430(4) 0.8340(4) 0.0269(11) Uani 1 1 d . . . . .
H3 H 0.550987 0.508742 0.898738 0.032 Uiso 1 1 calc R . . . .
C4 C 0.6297(6) 0.5038(3) 0.7559(4) 0.0232(10) Uani 1 1 d . . . . .
H4 H 0.670103 0.442724 0.765524 0.028 Uiso 1 1 calc R . . . .
C5 C 0.6382(5) 0.5572(3) 0.6634(4) 0.0183(9) Uani 1 1 d . . . . .
C6 C 0.7835(5) 0.4430(3) 0.5772(4) 0.0185(9) Uani 1 1 d . . . . .
H6 H 0.805429 0.397305 0.635594 0.022 Uiso 1 1 calc R . . . .
C7 C 0.8260(5) 0.4405(3) 0.4758(4) 0.0175(9) Uani 1 1 d . . . . .
C8 C 0.9111(5) 0.3753(3) 0.4268(4) 0.0209(10) Uani 1 1 d . . . . .
H8 H 0.950503 0.319891 0.466173 0.025 Uiso 1 1 calc R . . . .
C9 C 0.9339(5) 0.3941(3) 0.3242(4) 0.0230(10) Uani 1 1 d . . . . .
H9 H 0.991093 0.351420 0.291537 0.028 Uiso 1 1 calc R . . . .
C10 C 0.8741(5) 0.4777(3) 0.2615(4) 0.0200(10) Uani 1 1 d . . . . .
C11 C 0.9003(6) 0.4946(3) 0.1539(4) 0.0262(11) Uani 1 1 d . . . . .
H11 H 0.958754 0.451233 0.123194 0.031 Uiso 1 1 calc R . . . .
C12 C 0.8433(6) 0.5725(3) 0.0925(4) 0.0250(11) Uani 1 1 d . . . . .
H12 H 0.864011 0.583278 0.020656 0.030 Uiso 1 1 calc R . . . .
C13 C 0.7542(6) 0.6363(3) 0.1358(4) 0.0272(11) Uani 1 1 d . . . . .
H13 H 0.710983 0.688886 0.091529 0.033 Uiso 1 1 calc R . . . .
C14 C 0.7288(5) 0.6232(3) 0.2422(4) 0.0196(9) Uani 1 1 d . . . . .
H14 H 0.670863 0.667616 0.271807 0.023 Uiso 1 1 calc R . . . .
C15 C 0.7883(5) 0.5448(3) 0.3063(4) 0.0163(9) Uani 1 1 d . . . . .
C16 C 0.7664(5) 0.5234(3) 0.4174(4) 0.0157(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 Cl1 2.2065(12) . ?
Zn1 Cl2 2.2031(12) . ?
Zn1 N3 2.065(3) . ?
Zn1 N1 2.069(3) . ?
N3 C1 1.347(5) . ?
N3 C5 1.336(6) . ?
N2 N1 1.388(5) . ?
N2 C5 1.414(5) . ?
N2 C6 1.356(5) . ?
N1 C16 1.342(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.368(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(6) . ?
C7 C8 1.432(6) . ?
C7 C16 1.420(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.340(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.450(6) . ?
C10 C11 1.407(6) . ?
C10 C15 1.427(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.369(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.404(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.396(6) . ?
C15 C16 1.444(6) . ?

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
Cl2 Zn1 Cl1 116.03(5) . . ?
N3 Zn1 Cl1 113.75(11) . . ?
N3 Zn1 Cl2 112.06(11) . . ?
N3 Zn1 N1 79.64(13) . . ?
N1 Zn1 Cl1 115.82(11) . . ?
N1 Zn1 Cl2 114.28(10) . . ?
C1 N3 Zn1 127.4(3) . . ?
C5 N3 Zn1 115.6(3) . . ?
C5 N3 C1 117.1(4) . . ?
N1 N2 C5 119.7(3) . . ?
C6 N2 N1 112.3(3) . . ?
C6 N2 C5 128.0(4) . . ?
N2 N1 Zn1 109.9(2) . . ?
C16 N1 Zn1 143.8(3) . . ?
C16 N1 N2 104.0(3) . . ?
N3 C1 H1 118.6 . . ?
N3 C1 C2 122.7(5) . . ?
C2 C1 H1 118.6 . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.1(4) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.6(4) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 121.4 . . ?
C3 C4 C5 117.2(4) . . ?
C5 C4 H4 121.4 . . ?
N3 C5 N2 113.9(4) . . ?
N3 C5 C4 124.3(4) . . ?
C4 C5 N2 121.8(4) . . ?
N2 C6 H6 126.6 . . ?
N2 C6 C7 106.8(4) . . ?
C7 C6 H6 126.6 . . ?
C6 C7 C8 133.3(4) . . ?
C6 C7 C16 105.6(4) . . ?
C16 C7 C8 121.1(4) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.5(4) . . ?
C9 C8 H8 120.8 . . ?
C8 C9 H9 119.0 . . ?
C8 C9 C10 122.1(4) . . ?
C10 C9 H9 119.0 . . ?
C11 C10 C9 120.2(4) . . ?
C11 C10 C15 118.1(4) . . ?
C15 C10 C9 121.6(4) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.2(4) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(4) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.5(4) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0(4) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C16 115.3(4) . . ?
C14 C15 C10 120.1(4) . . ?
C14 C15 C16 124.6(4) . . ?
N1 C16 C7 111.3(4) . . ?
N1 C16 C15 127.3(4) . . ?
C7 C16 C15 121.4(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_L2
_database_code_depnum_ccdc_archive 'CCDC 1938875'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2019-07-06 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;
_audit_creation_date             2019-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 N3'
_chemical_formula_sum            'C16 H11 N3'
_chemical_formula_weight         245.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.9823(4)
_cell_length_b                   13.3952(5)
_cell_length_c                   21.6046(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.7690(10)
_cell_angle_gamma                90
_cell_volume                     3463.6(2)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    9115
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.06
_cell_measurement_theta_min      3.49
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0675 before and 0.0618 after correction. The Ratio of minimum to maximum transmission is 0.9288. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            48385
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.909
_diffrn_ambient_temperature      149.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4989
_reflns_number_total             7934
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     514
_refine_ls_number_reflns         7934
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0573P)²+1.8560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1410
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12),
 C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C24(H24),
  C25(H25), C27(H27), C28(H28), C29(H29), C30(H30), C33(H33), C34(H34),
 C35(H35), C36(H36), C38(H38), C40(H40), C41(H41), C43(H43), C44(H44), C45(H45),
  C46(H46)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.20838(13) 0.83201(12) 0.30963(7) 0.0180(3) Uani 1 1 d . . . . .
N2 N 0.28016(13) 0.88355(11) 0.27429(7) 0.0176(3) Uani 1 1 d . . . . .
N3 N 0.31475(14) 0.99253(12) 0.19499(7) 0.0214(4) Uani 1 1 d . . . . .
C1 C 0.27840(17) 1.05584(15) 0.15026(9) 0.0241(4) Uani 1 1 d . . . . .
H1 H 0.332404 1.088503 0.126635 0.029 Uiso 1 1 calc R . . . .
C2 C 0.16695(17) 1.07614(15) 0.13667(9) 0.0221(4) Uani 1 1 d . . . . .
H2 H 0.144949 1.122074 0.104870 0.026 Uiso 1 1 calc R . . . .
C3 C 0.08814(17) 1.02783(15) 0.17056(9) 0.0215(4) Uani 1 1 d . . . . .
H3 H 0.010734 1.039497 0.161971 0.026 Uiso 1 1 calc R . . . .
C4 C 0.12302(16) 0.96249(14) 0.21700(9) 0.0197(4) Uani 1 1 d . . . . .
H4 H 0.070915 0.928388 0.241161 0.024 Uiso 1 1 calc R . . . .
C5 C 0.23726(16) 0.94865(13) 0.22696(8) 0.0165(4) Uani 1 1 d . . . . .
C6 C 0.38949(15) 0.86505(14) 0.28923(9) 0.0182(4) Uani 1 1 d . . . . .
H6 H 0.452250 0.893106 0.270363 0.022 Uiso 1 1 calc R . . . .
C7 C 0.39112(15) 0.79733(14) 0.33733(8) 0.0174(4) Uani 1 1 d . . . . .
C8 C 0.47734(16) 0.74645(14) 0.37265(9) 0.0196(4) Uani 1 1 d . . . . .
H8 H 0.553814 0.758541 0.365623 0.023 Uiso 1 1 calc R . . . .
C9 C 0.44759(16) 0.68071(14) 0.41631(9) 0.0197(4) Uani 1 1 d . . . . .
H9 H 0.504586 0.646085 0.439640 0.024 Uiso 1 1 calc R . . . .
C10 C 0.33229(16) 0.66114(14) 0.42881(8) 0.0172(4) Uani 1 1 d . . . . .
C11 C 0.30510(17) 0.59254(15) 0.47519(9) 0.0218(4) Uani 1 1 d . . . . .
H11 H 0.363096 0.559633 0.498764 0.026 Uiso 1 1 calc R . . . .
C12 C 0.19557(17) 0.57285(15) 0.48659(9) 0.0241(4) Uani 1 1 d . . . . .
H12 H 0.178331 0.526696 0.518120 0.029 Uiso 1 1 calc R . . . .
C13 C 0.10933(17) 0.62022(15) 0.45216(9) 0.0233(4) Uani 1 1 d . . . . .
H13 H 0.033750 0.605610 0.460048 0.028 Uiso 1 1 calc R . . . .
C14 C 0.13345(16) 0.68801(14) 0.40681(9) 0.0203(4) Uani 1 1 d . . . . .
H14 H 0.074423 0.720200 0.383644 0.024 Uiso 1 1 calc R . . . .
C15 C 0.24467(15) 0.70975(13) 0.39468(8) 0.0167(4) Uani 1 1 d . . . . .
C16 C 0.27709(15) 0.77936(14) 0.34790(8) 0.0162(4) Uani 1 1 d . . . . .
N4 N 0.20468(13) 0.48641(11) 0.31353(7) 0.0170(3) Uani 1 1 d . . . . .
N5 N 0.28077(13) 0.53795(11) 0.28130(7) 0.0164(3) Uani 1 1 d . . . . .
N6 N 0.32618(13) 0.65139(12) 0.20618(7) 0.0199(4) Uani 1 1 d . . . . .
C17 C 0.29568(17) 0.71694(14) 0.16154(9) 0.0219(4) Uani 1 1 d . . . . .
H17 H 0.352860 0.749383 0.140145 0.026 Uiso 1 1 calc R . . . .
C18 C 0.18619(17) 0.73989(14) 0.14494(9) 0.0220(4) Uani 1 1 d . . . . .
H18 H 0.168434 0.787374 0.113313 0.026 Uiso 1 1 calc R . . . .
C19 C 0.10277(16) 0.69184(14) 0.17563(9) 0.0207(4) Uani 1 1 d . . . . .
H19 H 0.026447 0.705828 0.165179 0.025 Uiso 1 1 calc R . . . .
C20 C 0.13127(16) 0.62348(14) 0.22152(8) 0.0187(4) Uani 1 1 d . . . . .
H20 H 0.075790 0.589327 0.243285 0.022 Uiso 1 1 calc R . . . .
C21 C 0.24399(15) 0.60668(13) 0.23455(8) 0.0157(4) Uani 1 1 d . . . . .
C22 C 0.38844(15) 0.51767(14) 0.29900(8) 0.0175(4) Uani 1 1 d . . . . .
H22 H 0.453432 0.545681 0.282416 0.021 Uiso 1 1 calc R . . . .
C23 C 0.38461(15) 0.44829(14) 0.34585(8) 0.0170(4) Uani 1 1 d . . . . .
C24 C 0.46642(16) 0.39788(15) 0.38438(9) 0.0211(4) Uani 1 1 d . . . . .
H24 H 0.543841 0.408994 0.379623 0.025 Uiso 1 1 calc R . . . .
C25 C 0.43167(17) 0.33403(15) 0.42776(9) 0.0220(4) Uani 1 1 d . . . . .
H25 H 0.486060 0.299604 0.453101 0.026 Uiso 1 1 calc R . . . .
C26 C 0.31507(16) 0.31616(14) 0.43705(8) 0.0195(4) Uani 1 1 d . . . . .
C27 C 0.28135(18) 0.25014(15) 0.48371(9) 0.0243(4) Uani 1 1 d . . . . .
H27 H 0.336298 0.217881 0.509820 0.029 Uiso 1 1 calc R . . . .
C28 C 0.17036(18) 0.23212(15) 0.49171(9) 0.0256(5) Uani 1 1 d . . . . .
H28 H 0.149036 0.187942 0.523447 0.031 Uiso 1 1 calc R . . . .
C29 C 0.08822(17) 0.27845(15) 0.45339(9) 0.0234(4) Uani 1 1 d . . . . .
H29 H 0.011506 0.264777 0.458793 0.028 Uiso 1 1 calc R . . . .
C30 C 0.11821(16) 0.34353(14) 0.40805(9) 0.0200(4) Uani 1 1 d . . . . .
H30 H 0.062054 0.375035 0.382376 0.024 Uiso 1 1 calc R . . . .
C31 C 0.23133(16) 0.36389(14) 0.39935(8) 0.0173(4) Uani 1 1 d . . . . .
C32 C 0.26845(15) 0.43196(13) 0.35310(8) 0.0159(4) Uani 1 1 d . . . . .
N7 N 0.28895(13) 0.34037(11) 0.18842(7) 0.0169(3) Uani 1 1 d . . . . .
N8 N 0.21470(12) 0.28888(11) 0.22175(7) 0.0159(3) Uani 1 1 d . . . . .
N9 N 0.17385(13) 0.17713(12) 0.29872(7) 0.0189(3) Uani 1 1 d . . . . .
C33 C 0.20675(16) 0.11248(14) 0.34331(9) 0.0211(4) Uani 1 1 d . . . . .
H33 H 0.150894 0.080472 0.365946 0.025 Uiso 1 1 calc R . . . .
C34 C 0.31691(17) 0.08983(14) 0.35818(9) 0.0219(4) Uani 1 1 d . . . . .
H34 H 0.336370 0.043401 0.390143 0.026 Uiso 1 1 calc R . . . .
C35 C 0.39861(17) 0.13646(15) 0.32535(9) 0.0220(4) Uani 1 1 d . . . . .
H35 H 0.475307 0.121801 0.334188 0.026 Uiso 1 1 calc R . . . .
C36 C 0.36746(16) 0.20460(14) 0.27956(8) 0.0188(4) Uani 1 1 d . . . . .
H36 H 0.421473 0.238609 0.256641 0.023 Uiso 1 1 calc R . . . .
C37 C 0.25399(15) 0.22105(13) 0.26860(8) 0.0163(4) Uani 1 1 d . . . . .
C38 C 0.10663(15) 0.30854(14) 0.20509(9) 0.0177(4) Uani 1 1 d . . . . .
H38 H 0.042480 0.280405 0.222513 0.021 Uiso 1 1 calc R . . . .
C39 C 0.10818(15) 0.37756(14) 0.15780(8) 0.0168(4) Uani 1 1 d . . . . .
C40 C 0.02479(16) 0.42936(14) 0.12085(9) 0.0193(4) Uani 1 1 d . . . . .
H40 H -0.052356 0.418136 0.126454 0.023 Uiso 1 1 calc R . . . .
C41 C 0.05799(16) 0.49469(14) 0.07776(9) 0.0199(4) Uani 1 1 d . . . . .
H41 H 0.002781 0.530138 0.053582 0.024 Uiso 1 1 calc R . . . .
C42 C 0.17434(16) 0.51253(14) 0.06715(8) 0.0187(4) Uani 1 1 d . . . . .
C43 C 0.20636(17) 0.57935(15) 0.02067(9) 0.0224(4) Uani 1 1 d . . . . .
H43 H 0.150382 0.612327 -0.004366 0.027 Uiso 1 1 calc R . . . .
C44 C 0.31709(18) 0.59753(15) 0.01099(9) 0.0250(4) Uani 1 1 d . . . . .
H44 H 0.337007 0.642288 -0.020754 0.030 Uiso 1 1 calc R . . . .
C45 C 0.40048(17) 0.55017(15) 0.04785(9) 0.0228(4) Uani 1 1 d . . . . .
H45 H 0.476894 0.564059 0.041674 0.027 Uiso 1 1 calc R . . . .
C46 C 0.37227(16) 0.48354(14) 0.09303(9) 0.0193(4) Uani 1 1 d . . . . .
H46 H 0.429378 0.451058 0.117520 0.023 Uiso 1 1 calc R . . . .
C47 C 0.25967(16) 0.46330(14) 0.10312(8) 0.0169(4) Uani 1 1 d . . . . .
C48 C 0.22343(15) 0.39451(13) 0.14929(8) 0.0154(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.365(2) . ?
N1 C16 1.339(2) . ?
N2 C5 1.421(2) . ?
N2 C6 1.357(2) . ?
N3 C1 1.342(3) . ?
N3 C5 1.322(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.381(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(3) . ?
C7 C8 1.428(3) . ?
C7 C16 1.417(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.351(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.444(3) . ?
C10 C11 1.409(3) . ?
C10 C15 1.413(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.373(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.396(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.377(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.401(3) . ?
C15 C16 1.442(3) . ?
N4 N5 1.362(2) . ?
N4 C32 1.335(2) . ?
N5 C21 1.421(2) . ?
N5 C22 1.355(2) . ?
N6 C17 1.342(3) . ?
N6 C21 1.328(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.380(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.377(3) . ?
C23 C24 1.425(3) . ?
C23 C32 1.425(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.349(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.441(3) . ?
C26 C27 1.414(3) . ?
C26 C31 1.414(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.371(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.400(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.372(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.404(3) . ?
C31 C32 1.439(3) . ?
N7 N8 1.359(2) . ?
N7 C48 1.339(2) . ?
N8 C37 1.423(2) . ?
N8 C38 1.353(2) . ?
N9 C33 1.340(2) . ?
N9 C37 1.324(2) . ?
C33 H33 0.9500 . ?
C33 C34 1.377(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.385(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.384(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.386(3) . ?
C38 H38 0.9500 . ?
C38 C39 1.379(3) . ?
C39 C40 1.428(3) . ?
C39 C48 1.420(2) . ?
C40 H40 0.9500 . ?
C40 C41 1.352(3) . ?
C41 H41 0.9500 . ?
C41 C42 1.444(3) . ?
C42 C43 1.412(3) . ?
C42 C47 1.417(3) . ?
C43 H43 0.9500 . ?
C43 C44 1.375(3) . ?
C44 H44 0.9500 . ?
C44 C45 1.399(3) . ?
C45 H45 0.9500 . ?
C45 C46 1.377(3) . ?
C46 H46 0.9500 . ?
C46 C47 1.404(3) . ?
C47 C48 1.440(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N1 N2 103.09(15) . . ?
N1 N2 C5 119.81(15) . . ?
C6 N2 N1 113.69(15) . . ?
C6 N2 C5 126.50(16) . . ?
C5 N3 C1 116.46(17) . . ?
N3 C1 H1 118.2 . . ?
N3 C1 C2 123.67(19) . . ?
C2 C1 H1 118.2 . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.25(18) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.39(19) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 121.3 . . ?
C3 C4 C5 117.32(18) . . ?
C5 C4 H4 121.3 . . ?
N3 C5 N2 114.21(16) . . ?
N3 C5 C4 124.90(18) . . ?
C4 C5 N2 120.89(17) . . ?
N2 C6 H6 126.9 . . ?
N2 C6 C7 106.13(16) . . ?
C7 C6 H6 126.9 . . ?
C6 C7 C8 134.47(17) . . ?
C6 C7 C16 104.75(17) . . ?
C16 C7 C8 120.75(17) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.42(17) . . ?
C9 C8 H8 120.8 . . ?
C8 C9 H9 118.8 . . ?
C8 C9 C10 122.41(18) . . ?
C10 C9 H9 118.8 . . ?
C11 C10 C9 120.50(17) . . ?
C11 C10 C15 118.69(17) . . ?
C15 C10 C9 120.81(17) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.59(19) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.43(18) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.23(18) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.29(18) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C16 116.44(16) . . ?
C14 C15 C10 119.76(17) . . ?
C14 C15 C16 123.80(17) . . ?
N1 C16 C7 112.33(16) . . ?
N1 C16 C15 126.50(17) . . ?
C7 C16 C15 121.16(17) . . ?
C32 N4 N5 103.16(15) . . ?
N4 N5 C21 119.98(15) . . ?
C22 N5 N4 113.95(15) . . ?
C22 N5 C21 126.07(16) . . ?
C21 N6 C17 116.40(17) . . ?
N6 C17 H17 118.1 . . ?
N6 C17 C18 123.77(18) . . ?
C18 C17 H17 118.1 . . ?
C17 C18 H18 120.9 . . ?
C17 C18 C19 118.16(18) . . ?
C19 C18 H18 120.9 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.54(18) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 121.3 . . ?
C19 C20 C21 117.31(17) . . ?
C21 C20 H20 121.3 . . ?
N6 C21 N5 114.14(16) . . ?
N6 C21 C20 124.81(17) . . ?
C20 C21 N5 121.05(16) . . ?
N5 C22 H22 126.9 . . ?
N5 C22 C23 106.12(16) . . ?
C23 C22 H22 126.9 . . ?
C22 C23 C24 134.67(18) . . ?
C22 C23 C32 104.59(16) . . ?
C32 C23 C24 120.72(17) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 C23 118.65(18) . . ?
C25 C24 H24 120.7 . . ?
C24 C25 H25 118.8 . . ?
C24 C25 C26 122.40(18) . . ?
C26 C25 H25 118.8 . . ?
C27 C26 C25 121.02(18) . . ?
C31 C26 C25 120.69(17) . . ?
C31 C26 C27 118.29(18) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 C26 120.81(19) . . ?
C28 C27 H27 119.6 . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.39(18) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 119.9 . . ?
C30 C29 C28 120.19(19) . . ?
C30 C29 H29 119.9 . . ?
C29 C30 H30 119.8 . . ?
C29 C30 C31 120.45(19) . . ?
C31 C30 H30 119.8 . . ?
C26 C31 C32 116.87(17) . . ?
C30 C31 C26 119.85(17) . . ?
C30 C31 C32 123.28(17) . . ?
N4 C32 C23 112.18(16) . . ?
N4 C32 C31 127.16(17) . . ?
C23 C32 C31 120.66(17) . . ?
C48 N7 N8 103.32(15) . . ?
N7 N8 C37 119.88(15) . . ?
C38 N8 N7 113.76(15) . . ?
C38 N8 C37 126.36(16) . . ?
C37 N9 C33 116.45(17) . . ?
N9 C33 H33 118.1 . . ?
N9 C33 C34 123.72(18) . . ?
C34 C33 H33 118.1 . . ?
C33 C34 H34 120.8 . . ?
C33 C34 C35 118.32(18) . . ?
C35 C34 H34 120.8 . . ?
C34 C35 H35 120.3 . . ?
C36 C35 C34 119.37(18) . . ?
C36 C35 H35 120.3 . . ?
C35 C36 H36 121.5 . . ?
C35 C36 C37 117.09(18) . . ?
C37 C36 H36 121.5 . . ?
N9 C37 N8 114.24(16) . . ?
N9 C37 C36 125.03(17) . . ?
C36 C37 N8 120.73(17) . . ?
N8 C38 H38 126.9 . . ?
N8 C38 C39 106.30(16) . . ?
C39 C38 H38 126.9 . . ?
C38 C39 C40 134.90(17) . . ?
C38 C39 C48 104.54(16) . . ?
C48 C39 C40 120.56(17) . . ?
C39 C40 H40 120.7 . . ?
C41 C40 C39 118.57(17) . . ?
C41 C40 H40 120.7 . . ?
C40 C41 H41 118.8 . . ?
C40 C41 C42 122.36(18) . . ?
C42 C41 H41 118.8 . . ?
C43 C42 C41 121.03(17) . . ?
C43 C42 C47 118.13(17) . . ?
C47 C42 C41 120.84(17) . . ?
C42 C43 H43 119.4 . . ?
C44 C43 C42 121.19(18) . . ?
C44 C43 H43 119.4 . . ?
C43 C44 H44 120.0 . . ?
C43 C44 C45 120.06(18) . . ?
C45 C44 H44 120.0 . . ?
C44 C45 H45 119.9 . . ?
C46 C45 C44 120.29(18) . . ?
C46 C45 H45 119.9 . . ?
C45 C46 H46 119.8 . . ?
C45 C46 C47 120.41(18) . . ?
C47 C46 H46 119.8 . . ?
C42 C47 C48 116.35(16) . . ?
C46 C47 C42 119.90(17) . . ?
C46 C47 C48 123.74(17) . . ?
N7 C48 C39 112.08(16) . . ?
N7 C48 C47 126.62(17) . . ?
C39 C48 C47 121.30(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1938878'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2019-07-06 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;
_audit_creation_date             2019-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 Cu N5 O6'
_chemical_formula_sum            'C16 H11 Cu N5 O6'
_chemical_formula_weight         432.84
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.8817(4)
_cell_length_b                   8.3565(4)
_cell_length_c                   13.6764(7)
_cell_angle_alpha                84.043(2)
_cell_angle_beta                 89.244(2)
_cell_angle_gamma                63.9420(10)
_cell_volume                     804.31(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7725
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.66
_cell_measurement_theta_min      3.00
_shelx_estimated_absorpt_T_max   0.817
_shelx_estimated_absorpt_T_min   0.702
_exptl_absorpt_coefficient_mu    1.408
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0483 before and 0.0384 after correction. The Ratio of minimum to maximum transmission is 0.9016. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             438
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14528
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.709
_diffrn_reflns_theta_min         2.730
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4265
_reflns_number_total             4956
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4956
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0285
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0253P)²+0.4793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0631
_refine_ls_wR_factor_ref         0.0666
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12),
 C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.52758(3) 0.19993(2) 0.80410(2) 0.01537(5) Uani 1 1 d . . . . .
O1 O 0.66804(18) -0.06104(14) 0.84862(8) 0.0225(2) Uani 1 1 d . . . . .
O2 O 0.7582(2) -0.00523(17) 0.70498(10) 0.0358(3) Uani 1 1 d . . . . .
O3 O 0.89015(19) -0.27613(16) 0.77978(10) 0.0315(3) Uani 1 1 d . . . . .
O4 O 0.31308(17) 0.16845(16) 0.75168(8) 0.0228(2) Uani 1 1 d . . . . .
O5 O 0.25832(18) 0.21441(17) 0.90427(9) 0.0267(3) Uani 1 1 d . . . . .
O6 O 0.06427(18) 0.16048(18) 0.81706(9) 0.0301(3) Uani 1 1 d . . . . .
N3 N 0.65867(17) 0.26734(16) 0.90181(9) 0.0141(2) Uani 1 1 d . . . . .
N2 N 0.52938(17) 0.53064(15) 0.80010(9) 0.0140(2) Uani 1 1 d . . . . .
N1 N 0.47184(17) 0.44084(15) 0.73979(9) 0.0138(2) Uani 1 1 d . . . . .
N4 N 0.77819(19) -0.11838(17) 0.77565(10) 0.0205(3) Uani 1 1 d . . . . .
N5 N 0.20662(18) 0.18172(17) 0.82620(9) 0.0181(2) Uani 1 1 d . . . . .
C1 C 0.7563(2) 0.16465(19) 0.98325(11) 0.0163(3) Uani 1 1 d . . . . .
H1 H 0.770378 0.045381 0.995693 0.020 Uiso 1 1 calc R . . . .
C2 C 0.8362(2) 0.2286(2) 1.04906(11) 0.0180(3) Uani 1 1 d . . . . .
H2 H 0.903530 0.154949 1.106559 0.022 Uiso 1 1 calc R . . . .
C3 C 0.8167(2) 0.4027(2) 1.02990(11) 0.0188(3) Uani 1 1 d . . . . .
H3 H 0.872585 0.448136 1.073949 0.023 Uiso 1 1 calc R . . . .
C4 C 0.7162(2) 0.50939(19) 0.94687(11) 0.0173(3) Uani 1 1 d . . . . .
H4 H 0.701067 0.628709 0.932459 0.021 Uiso 1 1 calc R . . . .
C5 C 0.6383(2) 0.43547(18) 0.88534(10) 0.0137(2) Uani 1 1 d . . . . .
C6 C 0.4722(2) 0.70412(18) 0.76460(11) 0.0160(3) Uani 1 1 d . . . . .
H6 H 0.494236 0.791067 0.794692 0.019 Uiso 1 1 calc R . . . .
C7 C 0.3760(2) 0.73091(18) 0.67672(11) 0.0151(3) Uani 1 1 d . . . . .
C8 C 0.2910(2) 0.88216(19) 0.60468(11) 0.0182(3) Uani 1 1 d . . . . .
H8 H 0.285811 0.994779 0.615243 0.022 Uiso 1 1 calc R . . . .
C9 C 0.2184(2) 0.86074(19) 0.52131(11) 0.0181(3) Uani 1 1 d . . . . .
H9 H 0.162738 0.960134 0.472372 0.022 Uiso 1 1 calc R . . . .
C10 C 0.22206(19) 0.69160(19) 0.50359(11) 0.0157(3) Uani 1 1 d . . . . .
C11 C 0.1457(2) 0.6769(2) 0.41437(11) 0.0189(3) Uani 1 1 d . . . . .
H11 H 0.087986 0.779214 0.367414 0.023 Uiso 1 1 calc R . . . .
C12 C 0.1539(2) 0.5152(2) 0.39456(11) 0.0210(3) Uani 1 1 d . . . . .
H12 H 0.099372 0.507385 0.334765 0.025 Uiso 1 1 calc R . . . .
C13 C 0.2417(2) 0.3633(2) 0.46185(11) 0.0203(3) Uani 1 1 d . . . . .
H13 H 0.249491 0.251850 0.446852 0.024 Uiso 1 1 calc R . . . .
C14 C 0.3174(2) 0.3733(2) 0.55016(11) 0.0172(3) Uani 1 1 d . . . . .
H14 H 0.377941 0.268722 0.595344 0.021 Uiso 1 1 calc R . . . .
C15 C 0.30520(19) 0.53790(19) 0.57331(10) 0.0143(2) Uani 1 1 d . . . . .
C16 C 0.38090(19) 0.56250(18) 0.66260(10) 0.0135(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9933(11) . ?
Cu1 O2 2.4001(13) . ?
Cu1 O4 1.9757(11) . ?
Cu1 N3 1.9685(12) . ?
Cu1 N1 1.9711(12) . ?
O1 N4 1.3001(18) . ?
O2 N4 1.2396(18) . ?
O3 N4 1.2180(17) . ?
O4 N5 1.2940(16) . ?
O5 N5 1.2452(17) . ?
O6 N5 1.2203(17) . ?
N3 C1 1.3464(19) . ?
N3 C5 1.3369(17) . ?
N2 N1 1.3734(15) . ?
N2 C5 1.4008(18) . ?
N2 C6 1.3513(17) . ?
N1 C16 1.3487(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.380(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3864(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.374(2) . ?
C7 C8 1.426(2) . ?
C7 C16 1.4238(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.345(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.446(2) . ?
C10 C11 1.408(2) . ?
C10 C15 1.418(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.393(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.381(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.4052(19) . ?
C15 C16 1.4382(19) . ?

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 Cu1 O2 57.88(4) . . ?
O4 Cu1 O1 91.76(5) . . ?
O4 Cu1 O2 94.95(5) . . ?
N3 Cu1 O1 93.30(5) . . ?
N3 Cu1 O2 108.91(5) . . ?
N3 Cu1 O4 154.46(5) . . ?
N3 Cu1 N1 82.33(5) . . ?
N1 Cu1 O1 160.45(5) . . ?
N1 Cu1 O2 105.44(5) . . ?
N1 Cu1 O4 100.40(5) . . ?
N4 O1 Cu1 101.62(9) . . ?
N4 O2 Cu1 84.31(9) . . ?
N5 O4 Cu1 104.09(8) . . ?
C1 N3 Cu1 126.47(10) . . ?
C5 N3 Cu1 114.66(10) . . ?
C5 N3 C1 118.80(12) . . ?
N1 N2 C5 118.48(11) . . ?
C6 N2 N1 112.21(11) . . ?
C6 N2 C5 129.29(12) . . ?
N2 N1 Cu1 110.23(9) . . ?
C16 N1 Cu1 144.39(10) . . ?
C16 N1 N2 104.89(11) . . ?
O2 N4 O1 116.13(13) . . ?
O3 N4 O1 119.33(14) . . ?
O3 N4 O2 124.53(15) . . ?
O5 N5 O4 116.96(12) . . ?
O6 N5 O4 119.24(13) . . ?
O6 N5 O5 123.80(13) . . ?
N3 C1 H1 119.2 . . ?
N3 C1 C2 121.52(13) . . ?
C2 C1 H1 119.2 . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 118.96(14) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.99(14) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 121.3 . . ?
C3 C4 C5 117.33(13) . . ?
C5 C4 H4 121.3 . . ?
N3 C5 N2 113.56(12) . . ?
N3 C5 C4 123.37(13) . . ?
C4 C5 N2 123.07(12) . . ?
N2 C6 H6 126.5 . . ?
N2 C6 C7 106.99(12) . . ?
C7 C6 H6 126.5 . . ?
C6 C7 C8 132.68(13) . . ?
C6 C7 C16 105.79(12) . . ?
C16 C7 C8 121.45(13) . . ?
C7 C8 H8 121.0 . . ?
C9 C8 C7 118.05(13) . . ?
C9 C8 H8 121.0 . . ?
C8 C9 H9 118.9 . . ?
C8 C9 C10 122.27(14) . . ?
C10 C9 H9 118.9 . . ?
C11 C10 C9 119.66(13) . . ?
C11 C10 C15 118.85(13) . . ?
C15 C10 C9 121.47(13) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.56(14) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.28(14) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.60(14) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.10(14) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C16 115.85(12) . . ?
C14 C15 C10 119.53(13) . . ?
C14 C15 C16 124.54(13) . . ?
N1 C16 C7 110.08(12) . . ?
N1 C16 C15 128.96(12) . . ?
C7 C16 C15 120.87(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1938877'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2019-07-06 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;
_audit_creation_date             2019-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 Cl2 N4 Zn'
_chemical_formula_sum            'C22 H16 Cl2 N4 Zn'
_chemical_formula_weight         472.66
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   27.835(4)
_cell_length_b                   5.1802(7)
_cell_length_c                   6.7211(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.439(3)
_cell_angle_gamma                90
_cell_volume                     964.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2378
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.968
_cell_measurement_theta_min      3.045
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.734
_exptl_absorpt_coefficient_mu    1.567
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1066 before and 0.0769 after correction. The Ratio of minimum to maximum transmission is 0.7045. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5814
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.034
_diffrn_reflns_theta_min         2.940
_diffrn_ambient_temperature      150.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1710
_reflns_number_total             1902
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1902
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      0.960
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0632
_refine_ls_wR_factor_ref         0.0654
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.95(2)
 0.05(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Restrained distances
 N2-H2
 0.88 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.500000 0.89395(11) 0.000000 0.0200(2) Uani 1 2 d S T P . .
Cl1 Cl 0.53780(4) 1.1303(2) 0.24708(16) 0.0283(3) Uani 1 1 d . . . . .
N1 N 0.45250(13) 0.6921(7) 0.1452(5) 0.0224(9) Uani 1 1 d . . . . .
N2 N 0.42364(14) 0.4980(7) 0.0697(6) 0.0224(9) Uani 1 1 d D . . . .
C1 C 0.43875(15) 0.7495(9) 0.3226(6) 0.0230(10) Uani 1 1 d . . . . .
H1 H 0.452734 0.880826 0.408200 0.028 Uiso 1 1 calc R . . . .
C2 C 0.40072(16) 0.5899(9) 0.3667(7) 0.0215(10) Uani 1 1 d . . . . .
C3 C 0.37217(16) 0.5649(9) 0.5307(7) 0.0260(11) Uani 1 1 d . . . . .
H3 H 0.377789 0.672479 0.644996 0.031 Uiso 1 1 calc R . . . .
C4 C 0.33720(14) 0.3863(14) 0.5200(6) 0.0283(10) Uani 1 1 d . . . . .
H4 H 0.317744 0.370976 0.628119 0.034 Uiso 1 1 calc R . . . .
C5 C 0.32794(17) 0.2163(9) 0.3506(8) 0.0261(11) Uani 1 1 d . . . . .
C6 C 0.29094(17) 0.0322(10) 0.3414(8) 0.0316(12) Uani 1 1 d . . . . .
H6 H 0.271335 0.018502 0.449187 0.038 Uiso 1 1 calc R . . . .
C7 C 0.28249(16) -0.1283(14) 0.1803(8) 0.0361(12) Uani 1 1 d . . . . .
H7 H 0.257206 -0.251842 0.177570 0.043 Uiso 1 1 calc R . . . .
H2 H 0.4309(18) 0.397(11) -0.028(6) 0.043 Uiso 1 1 d DR . . . .
C8 C 0.31077(15) -0.1119(14) 0.0199(7) 0.0319(10) Uani 1 1 d . . . . .
H8 H 0.305040 -0.225703 -0.090651 0.038 Uiso 1 1 calc R . . . .
C9 C 0.34685(17) 0.0691(9) 0.0222(8) 0.0272(11) Uani 1 1 d . . . . .
H9 H 0.365809 0.081701 -0.087734 0.033 Uiso 1 1 calc R . . . .
C10 C 0.35581(16) 0.2349(9) 0.1858(7) 0.0231(10) Uani 1 1 d . . . . .
C11 C 0.39231(15) 0.4292(10) 0.2027(6) 0.0202(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 Cl1 2.2431(12) 2_655 ?
Zn1 Cl1 2.2432(12) . ?
Zn1 N1 2.010(4) . ?
Zn1 N1 2.010(4) 2_655 ?
N1 N2 1.355(5) . ?
N1 C1 1.321(5) . ?
N2 H2 0.88(3) . ?
N2 C11 1.354(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.397(6) . ?
C2 C3 1.425(6) . ?
C2 C11 1.383(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.340(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.443(7) . ?
C5 C6 1.401(7) . ?
C5 C10 1.414(7) . ?
C6 H6 0.9500 . ?
C6 C7 1.367(8) . ?
C7 H7 0.9500 . ?
C7 C8 1.397(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.373(8) . ?
C9 H9 0.9500 . ?
C9 C10 1.399(7) . ?
C10 C11 1.427(6) . ?

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
Cl1 Zn1 Cl1 113.86(7) 2_655 . ?
N1 Zn1 Cl1 102.03(11) 2_655 2_655 ?
N1 Zn1 Cl1 111.07(11) . 2_655 ?
N1 Zn1 Cl1 111.06(11) 2_655 . ?
N1 Zn1 Cl1 102.03(11) . . ?
N1 Zn1 N1 117.3(2) . 2_655 ?
N2 N1 Zn1 126.8(3) . . ?
C1 N1 Zn1 125.6(3) . . ?
C1 N1 N2 107.0(4) . . ?
N1 N2 H2 123(4) . . ?
C11 N2 N1 110.1(4) . . ?
C11 N2 H2 123(4) . . ?
N1 C1 H1 124.8 . . ?
N1 C1 C2 110.4(4) . . ?
C2 C1 H1 124.8 . . ?
C1 C2 C3 135.0(4) . . ?
C11 C2 C1 105.2(4) . . ?
C11 C2 C3 119.8(4) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 C2 118.5(4) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 H4 118.7 . . ?
C3 C4 C5 122.6(4) . . ?
C5 C4 H4 118.7 . . ?
C6 C5 C4 121.7(5) . . ?
C6 C5 C10 117.9(5) . . ?
C10 C5 C4 120.4(4) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.3(5) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.5(6) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.9(6) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.3(5) . . ?
C10 C9 H9 119.9 . . ?
C5 C10 C11 115.1(4) . . ?
C9 C10 C5 120.2(4) . . ?
C9 C10 C11 124.6(4) . . ?
N2 C11 C2 107.2(4) . . ?
N2 C11 C10 129.1(4) . . ?
C2 C11 C10 123.6(4) . . ?

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
N2 H2 Cl1 0.88(3) 2.25(3) 3.122(4) 170(5) 2_645 yes

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.95(2)
2 0.05(2)
