# 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_a40612a_0m
_database_code_depnum_ccdc_archive 'CCDC 1864868'
_audit_update_record             
;
2018-08-30 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 N12 O4 Zn2'
_chemical_formula_weight         634.22

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   19.885(6)
_cell_length_b                   21.893(6)
_cell_length_c                   14.279(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 126.457(3)
_cell_angle_gamma                90.00
_cell_volume                     5000(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.843
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1284
_exptl_absorpt_coefficient_mu    0.987
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12336
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         25.20
_reflns_number_total             4612
_reflns_number_gt                3672
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1294P)²+5.9029P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4612
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.2144
_refine_ls_wR_factor_gt          0.2038
_refine_ls_goodness_of_fit_ref   1.226
_refine_ls_restrained_S_all      1.226
_refine_ls_shift/su_max          2.953
_refine_ls_shift/su_mean         0.017

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.47146(4) 0.5000 1.07753(5) 0.0257(2) Uani 1 2 d S . .
Zn2 Zn 0.5000 0.41618(3) 1.5000 0.0265(2) Uani 1 2 d S . .
N1 N 0.0977(3) 0.13634(18) 0.5521(3) 0.0429(10) Uani 1 1 d . . .
N2 N 0.1418(4) 0.1302(2) 0.5121(5) 0.0777(18) Uani 1 1 d . . .
N3 N 0.1992(4) 0.1745(3) 0.5585(6) 0.091(2) Uani 1 1 d . . .
N4 N 0.1255(3) 0.18345(19) 0.6260(4) 0.0487(11) Uani 1 1 d . . .
N5 N 0.4592(3) 0.5000 1.2092(4) 0.0290(11) Uani 1 2 d S . .
N6 N 0.4778(2) 0.46827(14) 1.3698(3) 0.0270(7) Uani 1 1 d . . .
O1 O 0.3905(2) 0.43404(16) 0.9679(3) 0.0477(9) Uani 1 1 d . . .
O2 O 0.4358(2) 0.43508(16) 0.8581(3) 0.0474(9) Uani 1 1 d . . .
C1 C 0.3917(3) 0.4145(2) 0.8864(4) 0.0370(11) Uani 1 1 d . . .
C2 C 0.3362(3) 0.3613(2) 0.8185(4) 0.0448(12) Uani 1 1 d . . .
C3 C 0.3296(4) 0.3401(3) 0.7217(5) 0.0636(17) Uani 1 1 d . . .
H3 H 0.3580 0.3603 0.6975 0.076 Uiso 1 1 calc R . .
C4 C 0.2905(4) 0.3316(3) 0.8493(5) 0.0663(18) Uani 1 1 d . . .
H4 H 0.2920 0.3460 0.9118 0.080 Uiso 1 1 calc R . .
C5 C 0.2430(4) 0.2814(3) 0.7887(5) 0.073(2) Uani 1 1 d . . .
H5 H 0.2137 0.2616 0.8119 0.088 Uiso 1 1 calc R . .
C6 C 0.2822(4) 0.2901(3) 0.6614(5) 0.074(2) Uani 1 1 d . . .
H6 H 0.2796 0.2764 0.5977 0.089 Uiso 1 1 calc R . .
C7 C 0.2378(4) 0.2596(2) 0.6935(5) 0.0536(14) Uani 1 1 d . . .
C8 C 0.1873(4) 0.2060(2) 0.6271(5) 0.0520(14) Uani 1 1 d . . .
C9 C 0.4657(3) 0.45130(18) 1.2725(3) 0.0300(9) Uani 1 1 d . . .
C10 C 0.4569(4) 0.3862(2) 1.2346(4) 0.0480(13) Uani 1 1 d . . .
H10A H 0.5094 0.3719 1.2540 0.072 Uiso 1 1 calc R . .
H10B H 0.4151 0.3834 1.1520 0.072 Uiso 1 1 calc R . .
H10C H 0.4406 0.3615 1.2736 0.072 Uiso 1 1 calc R . .
C11 C 0.2158(19) 0.5000 0.512(6) 0.62(7) Uani 1 2 d S . .
H11A H 0.1971 0.4705 0.5415 0.927 Uiso 0.50 1 calc PR . .
H11B H 0.1940 0.4897 0.4333 0.927 Uiso 0.50 1 calc PR . .
H11C H 0.1963 0.5398 0.5136 0.927 Uiso 0.50 1 calc PR . .
N7 N 0.3046(17) 0.5000 0.582(2) 0.236(9) Uani 1 2 d S . .


_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 O1 2.032(3) . ?
Zn1 O1 2.032(3) 6_565 ?
Zn1 N5 2.034(5) . ?
Zn1 O2 2.062(3) 5_667 ?
Zn1 O2 2.062(3) 2_657 ?
Zn1 Zn1 3.0294(14) 5_667 ?
Zn2 N1 1.982(4) 7_557 ?
Zn2 N1 1.982(4) 8_556 ?
Zn2 N6 1.994(3) 2_658 ?
Zn2 N6 1.994(3) . ?
N1 N2 1.308(6) . ?
N1 N4 1.338(5) . ?
N1 Zn2 1.982(4) 7_557 ?
N2 N3 1.335(6) . ?
N3 C8 1.330(7) . ?
N4 C8 1.316(6) . ?
N5 C9 1.354(5) . ?
N5 C9 1.354(5) 6_565 ?
N6 C9 1.314(5) . ?
N6 N6 1.389(6) 6_565 ?
O1 C1 1.254(6) . ?
O2 C1 1.247(6) . ?
O2 Zn1 2.062(3) 5_667 ?
C1 C2 1.499(6) . ?
C2 C4 1.384(7) . ?
C2 C3 1.389(7) . ?
C3 C6 1.366(7) . ?
C4 C5 1.370(7) . ?
C5 C7 1.386(7) . ?
C6 C7 1.385(7) . ?
C7 C8 1.467(7) . ?
C9 C10 1.498(6) . ?
C11 N7 1.42(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
O1 Zn1 O1 90.5(2) . 6_565 ?
O1 Zn1 N5 103.70(14) . . ?
O1 Zn1 N5 103.70(14) 6_565 . ?
O1 Zn1 O2 157.26(13) . 5_667 ?
O1 Zn1 O2 86.72(16) 6_565 5_667 ?
N5 Zn1 O2 98.87(14) . 5_667 ?
O1 Zn1 O2 86.72(15) . 2_657 ?
O1 Zn1 O2 157.27(13) 6_565 2_657 ?
N5 Zn1 O2 98.87(14) . 2_657 ?
O2 Zn1 O2 87.2(2) 5_667 2_657 ?
O1 Zn1 Zn1 84.63(10) . 5_667 ?
O1 Zn1 Zn1 84.63(10) 6_565 5_667 ?
N5 Zn1 Zn1 167.97(15) . 5_667 ?
O2 Zn1 Zn1 72.64(10) 5_667 5_667 ?
O2 Zn1 Zn1 72.64(10) 2_657 5_667 ?
N1 Zn2 N1 109.1(3) 7_557 8_556 ?
N1 Zn2 N6 107.84(14) 7_557 2_658 ?
N1 Zn2 N6 110.92(15) 8_556 2_658 ?
N1 Zn2 N6 110.92(15) 7_557 . ?
N1 Zn2 N6 107.84(14) 8_556 . ?
N6 Zn2 N6 110.25(18) 2_658 . ?
N2 N1 N4 110.7(4) . . ?
N2 N1 Zn2 122.6(3) . 7_557 ?
N4 N1 Zn2 126.7(3) . 7_557 ?
N1 N2 N3 107.9(4) . . ?
C8 N3 N2 105.5(4) . . ?
C8 N4 N1 104.1(4) . . ?
C9 N5 C9 103.9(4) . 6_565 ?
C9 N5 Zn1 127.0(2) . . ?
C9 N5 Zn1 127.0(2) 6_565 . ?
C9 N6 N6 106.4(2) . 6_565 ?
C9 N6 Zn2 128.6(3) . . ?
N6 N6 Zn2 124.88(9) 6_565 . ?
C1 O1 Zn1 120.9(3) . . ?
C1 O2 Zn1 136.0(3) . 5_667 ?
O2 C1 O1 125.6(4) . . ?
O2 C1 C2 117.5(4) . . ?
O1 C1 C2 116.9(4) . . ?
C4 C2 C3 118.0(4) . . ?
C4 C2 C1 122.0(4) . . ?
C3 C2 C1 120.0(4) . . ?
C6 C3 C2 121.0(5) . . ?
C5 C4 C2 120.8(5) . . ?
C4 C5 C7 121.1(5) . . ?
C3 C6 C7 121.1(5) . . ?
C6 C7 C5 117.9(4) . . ?
C6 C7 C8 119.9(4) . . ?
C5 C7 C8 122.2(4) . . ?
N4 C8 N3 111.8(4) . . ?
N4 C8 C7 125.7(5) . . ?
N3 C8 C7 122.5(5) . . ?
N6 C9 N5 111.6(4) . . ?
N6 C9 C10 124.0(4) . . ?
N5 C9 C10 124.3(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.924
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.227
