# 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_ad-hnsf-03
_database_code_depnum_ccdc_archive 'CCDC 1914673'
loop_
_audit_author_name
_audit_author_address
DLM
;QUST
China
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2019-09-09 downloaded from the CCDC.
;
_audit_creation_date             2018-11-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H8 N4 O4 Zn'
_chemical_formula_sum            'C14 H8 N4 O4 Zn'
_chemical_formula_weight         361.61
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 O1 Zn1'
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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.9662(7)
_cell_length_b                   13.9304(8)
_cell_length_c                   13.3293(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.927(4)
_cell_angle_gamma                90
_cell_volume                     2758.7(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2208
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1600
_cell_measurement_theta_min      3.3090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.808
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5854
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.422
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.5095
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.8517
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -74.00  -44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.5341  178.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega   -4.00   36.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.5341  -99.0000   90.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega   44.00   70.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.5341   38.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -41.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -13.1747   77.0000  -30.0000 106
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0037918000
_diffrn_orient_matrix_UB_12      -0.0505896000
_diffrn_orient_matrix_UB_13      -0.0046366000
_diffrn_orient_matrix_UB_21      0.0414233000
_diffrn_orient_matrix_UB_22      -0.0054582000
_diffrn_orient_matrix_UB_23      0.0314529000
_diffrn_orient_matrix_UB_31      -0.0234447000
_diffrn_orient_matrix_UB_32      -0.0014761000
_diffrn_orient_matrix_UB_33      0.0431658000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2041
_reflns_number_total             2432
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2432
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.048
_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)+(0.0387P)²+3.2343P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0850
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H6(0.045) H14(0.05) H9(0.052) H13(0.037) H3(0.034) H8(0.037)
 H5(0.041) H7(0.045)
 Fixed X: H6(0.2441) H14(0.5604) H9(0.8256) H13(0.5109) H3(0.4528) H8(0.7997)
 H5(0.3701) H7(0.1384)
 Fixed Y: H6(1.0624) H14(0.7769) H9(0.6337) H13(0.5608) H3(0.9788) H8(0.9049)
 H5(1.1295) H7(1.1397)
 Fixed Z: H6(-0.0797) H14(0.4833) H9(0.4069) H13(0.6612) H3(0.1567) H8(0.3312)
 H5(0.1894) H7(0.0196)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.68121(2) 0.72260(3) 0.24104(2) 0.02526(14) Uani 1 1 d . U . . .
O1 O 0.60335(18) 0.6684(2) 0.33396(18) 0.0489(7) Uani 1 1 d . . . . .
N2 N 0.78577(18) 0.7638(2) 0.34149(18) 0.0323(7) Uani 1 1 d . . . . .
N4 N 0.61216(17) 0.6568(2) 0.55986(17) 0.0295(6) Uani 1 1 d . . . . .
N3 N 0.33825(16) 1.0819(2) 0.04630(17) 0.0278(6) Uani 1 1 d . . . . .
O4 O 0.64188(19) 0.9242(2) 0.23015(17) 0.0613(9) Uani 1 1 d . . . . .
O2 O 0.6401(2) 0.5214(2) 0.2965(2) 0.0682(9) Uani 1 1 d . . . . .
N1 N 0.74148(17) 0.6507(2) 0.13561(18) 0.0313(6) Uani 1 1 d . . . . .
O3 O 0.60418(18) 0.7962(2) 0.13707(18) 0.0488(7) Uani 1 1 d . . . . .
C6 C 0.2565(2) 1.0851(3) -0.0139(2) 0.0379(9) Uani 1 1 d . . . . .
H6 H 0.2441 1.0624 -0.0797 0.045 Uiso 1 1 calc R . . . .
C2 C 0.5522(2) 0.9452(2) 0.0736(2) 0.0258(7) Uani 1 1 d . . . . .
C14 C 0.6023(3) 0.7513(3) 0.5334(3) 0.0416(9) Uani 1 1 d . . . . .
H14 H 0.5604 0.7769 0.4833 0.050 Uiso 1 1 calc R . . . .
C12 C 0.5545(2) 0.5783(2) 0.5253(2) 0.0279(7) Uani 1 1 d . . . . .
C4 C 0.42072(19) 1.0415(2) 0.0216(2) 0.0252(7) Uani 1 1 d . . . . .
C9 C 0.8347(3) 0.6998(3) 0.4058(2) 0.0430(9) Uani 1 1 d . . . . .
H9 H 0.8256 0.6337 0.4069 0.052 Uiso 1 1 calc R . . . .
C1 C 0.6040(2) 0.8844(3) 0.1545(2) 0.0333(8) Uani 1 1 d . . . . .
C13 C 0.5061(2) 0.5357(3) 0.5961(2) 0.0311(8) Uani 1 1 d . . . . .
H13 H 0.5109 0.5608 0.6612 0.037 Uiso 1 1 calc R . . . .
C3 C 0.4722(2) 0.9873(2) 0.0935(2) 0.0284(7) Uani 1 1 d . . . . .
H3 H 0.4528 0.9788 0.1567 0.034 Uiso 1 1 calc R . . . .
C8 C 0.8197(2) 0.8484(3) 0.3636(2) 0.0305(7) Uani 1 1 d . . . . .
H8 H 0.7997 0.9049 0.3312 0.037 Uiso 1 1 calc R . . . .
C5 C 0.3254(2) 1.1224(3) 0.1351(2) 0.0341(8) Uani 1 1 d . . . . .
H5 H 0.3701 1.1295 0.1894 0.041 Uiso 1 1 calc R . . . .
C11 C 0.5486(2) 0.5423(2) 0.4271(2) 0.0275(7) Uani 1 1 d . . . . .
C10 C 0.6026(2) 0.5803(3) 0.3455(2) 0.0333(8) Uani 1 1 d . . . . .
C7 C 0.1987(2) 1.1276(3) 0.0416(2) 0.0378(9) Uani 1 1 d . . . . .
H7 H 0.1384 1.1397 0.0196 0.045 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.0264(2) 0.0290(2) 0.0213(2) 0.00160(14) 0.00660(14) 0.00006(17)
O1 0.0587(17) 0.0458(18) 0.0478(14) 0.0100(12) 0.0301(12) -0.0045(14)
N2 0.0324(15) 0.0368(18) 0.0268(14) 0.0015(12) 0.0003(11) -0.0055(14)
N4 0.0298(14) 0.0338(17) 0.0239(13) 0.0037(11) -0.0004(11) -0.0057(13)
N3 0.0257(13) 0.0352(17) 0.0239(13) 0.0025(11) 0.0084(10) 0.0080(13)
O4 0.0619(17) 0.086(2) 0.0328(13) -0.0045(14) -0.0079(12) 0.0213(17)
O2 0.097(2) 0.062(2) 0.0554(17) 0.0039(15) 0.0480(16) 0.0068(18)
N1 0.0266(14) 0.0419(18) 0.0269(13) -0.0013(12) 0.0095(11) 0.0067(13)
O3 0.0564(17) 0.0445(18) 0.0456(14) 0.0154(12) 0.0063(12) 0.0165(14)
C6 0.0315(18) 0.052(2) 0.0303(17) -0.0103(16) 0.0055(14) 0.0002(17)
C2 0.0275(16) 0.0272(18) 0.0234(15) 0.0031(13) 0.0057(12) 0.0055(15)
C14 0.046(2) 0.034(2) 0.0410(19) 0.0068(16) -0.0103(16) 0.0006(18)
C12 0.0238(16) 0.0335(19) 0.0257(15) 0.0051(13) -0.0003(12) -0.0040(15)
C4 0.0236(15) 0.0297(18) 0.0234(15) -0.0019(13) 0.0073(12) 0.0055(14)
C9 0.054(2) 0.031(2) 0.0409(19) 0.0044(15) -0.0087(17) -0.0042(18)
C1 0.0274(17) 0.047(2) 0.0278(17) 0.0085(16) 0.0136(14) 0.0160(17)
C13 0.0321(17) 0.043(2) 0.0181(14) 0.0006(14) 0.0017(12) -0.0045(17)
C3 0.0320(17) 0.036(2) 0.0188(14) 0.0034(13) 0.0102(12) 0.0109(16)
C8 0.0327(18) 0.031(2) 0.0267(15) 0.0051(13) 0.0013(13) -0.0039(16)
C5 0.0308(18) 0.047(2) 0.0246(16) -0.0009(14) 0.0031(13) 0.0082(17)
C11 0.0234(15) 0.037(2) 0.0220(15) 0.0064(13) 0.0026(12) -0.0030(15)
C10 0.0303(18) 0.045(2) 0.0242(16) 0.0025(15) 0.0013(13) -0.0069(17)
C7 0.0239(17) 0.054(3) 0.0362(18) -0.0068(16) 0.0044(14) 0.0028(17)

_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 1.952(2) . ?
Zn1 N2 2.016(3) . ?
Zn1 N1 2.025(3) . ?
Zn1 O3 1.979(2) . ?
O1 C10 1.236(4) . ?
N2 C9 1.384(4) . ?
N2 C8 1.303(4) . ?
N4 C14 1.366(4) . ?
N4 C12 1.435(4) . ?
N4 C8 1.355(4) 7_666 ?
N3 C6 1.380(4) . ?
N3 C4 1.430(4) . ?
N3 C5 1.347(4) . ?
O4 C1 1.228(4) . ?
O2 C10 1.227(4) . ?
N1 C5 1.317(4) 3_545 ?
N1 C7 1.375(4) 3_545 ?
O3 C1 1.250(4) . ?
C6 C7 1.342(4) . ?
C2 C4 1.389(4) 5_675 ?
C2 C1 1.510(4) . ?
C2 C3 1.388(4) . ?
C14 C9 1.352(5) 7_666 ?
C12 C13 1.390(4) . ?
C12 C11 1.395(4) . ?
C4 C2 1.389(4) 5_675 ?
C4 C3 1.380(4) . ?
C9 C14 1.352(5) 7_666 ?
C13 C11 1.373(5) 5_666 ?
C8 N4 1.355(4) 7_666 ?
C5 N1 1.316(4) 3_455 ?
C11 C13 1.373(5) 5_666 ?
C11 C10 1.526(4) . ?
C7 N1 1.375(4) 3_455 ?

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 N2 99.42(11) . . ?
O1 Zn1 N1 126.80(12) . . ?
O1 Zn1 O3 107.64(11) . . ?
N2 Zn1 N1 103.11(11) . . ?
O3 Zn1 N2 131.09(12) . . ?
O3 Zn1 N1 92.36(11) . . ?
C10 O1 Zn1 118.5(2) . . ?
C9 N2 Zn1 122.5(2) . . ?
C8 N2 Zn1 131.2(2) . . ?
C8 N2 C9 106.3(3) . . ?
C14 N4 C12 127.6(3) . . ?
C8 N4 C14 107.1(3) 7_666 . ?
C8 N4 C12 124.7(3) 7_666 . ?
C6 N3 C4 127.4(2) . . ?
C5 N3 C6 106.6(3) . . ?
C5 N3 C4 125.9(2) . . ?
C5 N1 Zn1 131.0(2) 3_545 . ?
C5 N1 C7 105.4(3) 3_545 3_545 ?
C7 N1 Zn1 123.4(2) 3_545 . ?
C1 O3 Zn1 113.2(2) . . ?
C7 C6 N3 106.3(3) . . ?
C4 C2 C1 123.1(3) 5_675 . ?
C3 C2 C4 118.2(3) . 5_675 ?
C3 C2 C1 118.7(2) . . ?
C9 C14 N4 106.5(3) 7_666 . ?
C13 C12 N4 116.8(3) . . ?
C13 C12 C11 120.3(3) . . ?
C11 C12 N4 122.8(3) . . ?
C2 C4 N3 120.8(3) 5_675 . ?
C3 C4 N3 118.6(2) . . ?
C3 C4 C2 120.5(3) . 5_675 ?
C14 C9 N2 109.0(3) 7_666 . ?
O4 C1 O3 125.8(3) . . ?
O4 C1 C2 118.6(3) . . ?
O3 C1 C2 115.5(3) . . ?
C11 C13 C12 122.0(3) 5_666 . ?
C4 C3 C2 121.3(3) . . ?
N2 C8 N4 111.1(3) . 7_666 ?
N1 C5 N3 111.6(3) 3_455 . ?
C12 C11 C10 124.5(3) . . ?
C13 C11 C12 117.6(3) 5_666 . ?
C13 C11 C10 117.8(3) 5_666 . ?
O1 C10 C11 116.5(3) . . ?
O2 C10 O1 125.9(3) . . ?
O2 C10 C11 117.6(3) . . ?
C6 C7 N1 110.1(3) . 3_455 ?

_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_sad
_database_code_depnum_ccdc_archive 'CCDC 1914674'
loop_
_audit_author_name
_audit_author_address
DLM
;QUST
China
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2019-09-09 downloaded from the CCDC.
;
_audit_creation_date             2018-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.5(C28 H16 Cd2 N8 O8)'
_chemical_formula_sum            'C14 H8 Cd N4 O4'
_chemical_formula_weight         408.64
_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'
Cd Cd -0.8075 1.2024 '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                   4.9130(10)
_cell_length_b                   13.234(3)
_cell_length_c                   10.065(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.83(3)
_cell_angle_gamma                90
_cell_volume                     646.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2221
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0655
_cell_measurement_theta_min      3.1420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.718
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.099
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4984
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.975
_diffrn_reflns_theta_min         3.078
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1014
_reflns_number_total             1132
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
'L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation (2013)'
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0187
_refine_ls_restrained_S_all      1.131
_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)+(0.0149P)²+0.5782P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0424
_refine_ls_wR_factor_ref         0.0436
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H5(0.024) H1(0.029) H2(0.033) H3(0.03)
 Fixed X: Cd1(0.5) H5(0.1624) H1(0.1095) H2(0.6815) H3(0.5463)
 Fixed Y: Cd1(0.5) H5(0.8837) H1(0.7142) H2(0.69) H3(0.8673)
 Fixed Z: Cd1(1) H5(1.1639) H1(1.0412) H2(0.8109) H3(0.8078)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cd1 Cd 0.5000 0.5000 1.0000 0.01834(10) Uani 1 2 d S T P . .
N2 N 0.2746(4) 0.82420(15) 0.9359(2) 0.0201(4) Uani 1 1 d . . . . .
N1 N 0.3964(4) 0.66331(15) 0.9383(2) 0.0248(5) Uani 1 1 d . . . . .
C4 C 0.1358(5) 0.91443(17) 0.9666(2) 0.0186(5) Uani 1 1 d . . . . .
C5 C 0.0963(5) 0.93082(18) 1.0982(2) 0.0204(5) Uani 1 1 d . . . . .
H5 H 0.1624 0.8837 1.1639 0.024 Uiso 1 1 calc R . . . .
O1 O 0.2818(4) 0.49564(13) 1.18494(18) 0.0324(5) Uani 1 1 d . . . . .
C7 C 0.0677(5) 0.53066(17) 1.2188(2) 0.0187(5) Uani 1 1 d . . . . .
C1 C 0.2349(5) 0.72964(18) 0.9838(3) 0.0241(6) Uani 1 1 d . . . . .
H1 H 0.1095 0.7142 1.0412 0.029 Uiso 1 1 calc R . . . .
O2 O 0.1251(4) 0.42535(14) 0.85429(18) 0.0304(4) Uani 1 1 d . . . . .
C6 C 0.0400(5) 0.98379(17) 0.8660(2) 0.0179(5) Uani 1 1 d . . . . .
C2 C 0.5487(5) 0.71745(19) 0.8570(3) 0.0277(6) Uani 1 1 d . . . . .
H2 H 0.6815 0.6900 0.8109 0.033 Uiso 1 1 calc R . . . .
C3 C 0.4753(5) 0.81553(19) 0.8548(3) 0.0254(6) Uani 1 1 d . . . . .
H3 H 0.5463 0.8673 0.8078 0.030 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cd1 0.02505(15) 0.01394(14) 0.01737(14) 0.00233(10) 0.00754(10) 0.00421(10)
N2 0.0277(11) 0.0155(10) 0.0192(10) 0.0011(9) 0.0102(9) 0.0065(9)
N1 0.0328(12) 0.0163(10) 0.0261(12) 0.0021(9) 0.0073(10) 0.0066(9)
C4 0.0228(12) 0.0131(11) 0.0211(12) -0.0002(10) 0.0072(10) 0.0028(10)
C5 0.0267(13) 0.0163(12) 0.0190(12) 0.0042(10) 0.0061(10) 0.0031(10)
O1 0.0411(11) 0.0345(11) 0.0258(10) 0.0012(8) 0.0186(9) 0.0080(9)
C7 0.0262(13) 0.0115(11) 0.0196(13) -0.0021(10) 0.0078(11) -0.0056(10)
C1 0.0320(14) 0.0187(12) 0.0238(13) 0.0043(10) 0.0116(11) 0.0027(11)
O2 0.0341(10) 0.0322(10) 0.0241(9) 0.0050(8) 0.0020(8) -0.0017(9)
C6 0.0209(12) 0.0163(12) 0.0178(12) 0.0004(9) 0.0071(10) -0.0009(9)
C2 0.0309(14) 0.0241(14) 0.0316(15) 0.0014(11) 0.0157(12) 0.0072(11)
C3 0.0282(13) 0.0197(12) 0.0312(14) 0.0036(11) 0.0143(12) 0.0018(11)

_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
Cd1 N1 2.285(2) . ?
Cd1 N1 2.285(2) 3_667 ?
Cd1 O1 2.2867(18) 3_667 ?
Cd1 O1 2.2868(18) . ?
Cd1 O2 2.3855(19) 3_667 ?
Cd1 O2 2.3855(19) . ?
N2 C4 1.432(3) . ?
N2 C1 1.366(3) . ?
N2 C3 1.378(3) . ?
N1 C1 1.312(3) . ?
N1 C2 1.390(3) . ?
C4 C5 1.385(3) . ?
C4 C6 1.394(3) . ?
C5 C6 1.389(3) 3_577 ?
O1 C7 1.244(3) . ?
C7 O2 1.250(3) 3_567 ?
C7 C6 1.521(3) 4_576 ?
O2 C7 1.250(3) 3_567 ?
C6 C5 1.389(3) 3_577 ?
C6 C7 1.521(3) 4_575 ?
C2 C3 1.346(4) . ?

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 Cd1 N1 180.0 3_667 . ?
N1 Cd1 O1 97.61(7) . . ?
N1 Cd1 O1 82.39(7) . 3_667 ?
N1 Cd1 O1 82.39(7) 3_667 . ?
N1 Cd1 O1 97.61(7) 3_667 3_667 ?
N1 Cd1 O2 83.93(7) 3_667 . ?
N1 Cd1 O2 96.07(7) 3_667 3_667 ?
N1 Cd1 O2 96.07(7) . . ?
N1 Cd1 O2 83.93(7) . 3_667 ?
O1 Cd1 O1 180.0 3_667 . ?
O1 Cd1 O2 85.66(7) . 3_667 ?
O1 Cd1 O2 94.34(7) . . ?
O1 Cd1 O2 85.66(7) 3_667 . ?
O1 Cd1 O2 94.34(7) 3_667 3_667 ?
O2 Cd1 O2 180.0 3_667 . ?
C1 N2 C4 126.1(2) . . ?
C1 N2 C3 106.7(2) . . ?
C3 N2 C4 127.2(2) . . ?
C1 N1 Cd1 131.27(17) . . ?
C1 N1 C2 105.6(2) . . ?
C2 N1 Cd1 122.02(16) . . ?
C5 C4 N2 118.6(2) . . ?
C5 C4 C6 120.7(2) . . ?
C6 C4 N2 120.7(2) . . ?
C4 C5 C6 121.3(2) . 3_577 ?
C7 O1 Cd1 137.33(17) . . ?
O1 C7 O2 127.5(2) . 3_567 ?
O1 C7 C6 115.2(2) . 4_576 ?
O2 C7 C6 117.3(2) 3_567 4_576 ?
N1 C1 N2 111.3(2) . . ?
C7 O2 Cd1 127.78(16) 3_567 . ?
C4 C6 C7 123.7(2) . 4_575 ?
C5 C6 C4 118.0(2) 3_577 . ?
C5 C6 C7 118.3(2) 3_577 4_575 ?
C3 C2 N1 109.8(2) . . ?
C2 C3 N2 106.6(2) . . ?

_iucr_refine_instructions_details 
;
TITL SAD in P2(1)/c
CELL 0.71073 4.913 13.2344 10.0646 90 98.829 90
ZERR 2 0.001 0.0026 0.002 0 0.03 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Cd N O
UNIT 28 16 2 8 8
 
L.S. 25
PLAN  5
omit-3 50
BOND
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\sad.hkl">
REM </olex2.extras>
 
WGHT    0.014900    0.578200
FVAR       0.43637
CD1   3    0.500000    0.500000    1.000000    10.50000    0.02505    0.01394 =
         0.01737    0.00233    0.00754    0.00421
N2    4    0.274580    0.824205    0.935869    11.00000    0.02770    0.01554 =
         0.01916    0.00114    0.01019    0.00652
N1    4    0.396380    0.663312    0.938274    11.00000    0.03279    0.01627 =
         0.02611    0.00214    0.00730    0.00662
C4    1    0.135811    0.914428    0.966587    11.00000    0.02281    0.01305 =
         0.02111   -0.00024    0.00724    0.00275
C5    1    0.096338    0.930823    1.098197    11.00000    0.02672    0.01625 =
         0.01901    0.00418    0.00607    0.00312
AFIX  43
H5    2    0.162422    0.883748    1.163898    11.00000   -1.20000
AFIX   0
O1    5    0.281821    0.495638    1.184937    11.00000    0.04111    0.03450 =
         0.02582    0.00124    0.01863    0.00800
C7    1    0.067690    0.530664    1.218794    11.00000    0.02623    0.01148 =
         0.01962   -0.00207    0.00782   -0.00558
C1    1    0.234874    0.729638    0.983759    11.00000    0.03199    0.01870 =
         0.02381    0.00431    0.01158    0.00273
AFIX  43
H1    2    0.109475    0.714244    1.041220    11.00000   -1.20000
AFIX   0
O2    5    0.125058    0.425348    0.854290    11.00000    0.03405    0.03218 =
         0.02415    0.00502    0.00202   -0.00168
C6    1    0.040049    0.983788    0.866012    11.00000    0.02086    0.01627 =
         0.01781    0.00044    0.00715   -0.00092
C2    1    0.548712    0.717451    0.856958    11.00000    0.03094    0.02406 =
         0.03156    0.00138    0.01573    0.00722
AFIX  43
H2    2    0.681495    0.690034    0.810904    11.00000   -1.20000
AFIX   0
C3    1    0.475330    0.815526    0.854817    11.00000    0.02822    0.01971 =
         0.03120    0.00361    0.01425    0.00180
AFIX  43
H3    2    0.546262    0.867283    0.807826    11.00000   -1.20000
AFIX   0
HKLF 4
 
REM  SAD in P2(1)/c
REM R1 =  0.0187 for    1014 Fo > 4sig(Fo)  and  0.0218 for all    1132 data
REM    106 parameters refined using      0 restraints
 
END  
     
WGHT      0.0149      0.5782 

REM Highest difference peak  0.352,  deepest hole -0.259,  1-sigma level  0.065
Q1    1   0.0149  1.0311  0.8823  11.00000  0.05    0.35
Q2    1   0.1958  0.9391  1.0409  11.00000  0.05    0.29
Q3    1   0.1413  0.9661  0.9182  11.00000  0.05    0.29
Q4    1   0.0166  0.9515  0.8977  11.00000  0.05    0.26
Q5    1   0.2117  0.8721  0.9597  11.00000  0.05    0.26

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0187 for 1014 Fo > 4sig(Fo) and 0.0218 for all 6400 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.35, deepest hole -0.26
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0218
  REM R1_gt = 0.0187
  REM wR_ref = 0.0436
  REM GOOF = 1.131
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 6400
  REM Reflections_gt = 1014
  REM Parameters = n/a
  REM Hole = -0.26
  REM Peak = 0.35
  REM Flack = n/a
;
_olex2_submission_special_instructions 'No special instructions were received'
