# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1936250'
loop_
_audit_author_name
_audit_author_address
'xiu mei zhang' 'Huaibei Normal University'
_audit_update_record             
;
2019-06-25 deposited with the CCDC.	2019-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N2 O8 Zn'
_chemical_formula_weight         403.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7164(7)
_cell_length_b                   9.6706(9)
_cell_length_c                   11.0779(11)
_cell_angle_alpha                68.2960(10)
_cell_angle_beta                 83.965(3)
_cell_angle_gamma                85.654(3)
_cell_volume                     763.19(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1130
_cell_measurement_theta_min      7.2530
_cell_measurement_theta_max      71.8060

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.709
_shelx_estimated_absorpt_T_min   0.773
_shelx_estimated_absorpt_T_max   0.899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7734
_exptl_absorpt_correction_T_max  0.8994
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4606
_diffrn_reflns_av_unetI/netI     0.1038
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.310
_diffrn_reflns_theta_max         66.050
_diffrn_reflns_theta_full        66.050
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2659
_reflns_number_gt                1777
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2659
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1446
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.55112(11) 1.16708(8) 0.19797(7) 0.0441(3) Uani 1 1 d . . . . .
O1 O 0.4843(5) 0.9667(4) 0.2324(4) 0.0484(11) Uani 1 1 d . . . . .
O2 O 0.3159(6) 0.9762(4) 0.4031(4) 0.0572(13) Uani 1 1 d . . . . .
O3 O 0.1396(6) 0.2080(4) 0.6589(4) 0.0555(12) Uani 1 1 d . . . . .
O4 O 0.4627(5) 0.2959(4) 0.2888(4) 0.0506(11) Uani 1 1 d . . . . .
O5 O 0.6058(6) 0.4918(4) 0.1597(4) 0.0622(14) Uani 1 1 d . . . . .
O6 O 0.7632(5) 1.0777(4) 0.3360(4) 0.0478(10) Uani 1 1 d . . . . .
H6B H 0.7938 0.9893 0.3418 0.057 Uiso 1 1 d R U . . .
H6C H 0.7247 1.0757 0.4114 0.057 Uiso 1 1 d R U . . .
O7 O 0.3427(6) 1.2505(5) 0.0592(4) 0.0630(13) Uani 1 1 d . . . . .
H7B H 0.3773 1.3258 -0.0060 0.076 Uiso 1 1 d R U . . .
H7C H 0.2516 1.2767 0.0968 0.076 Uiso 1 1 d R U . . .
O8 O 0.0699(6) 1.2612(6) 0.2685(5) 0.0823(16) Uani 1 1 d . . . . .
H8C H 0.1474 1.1940 0.3009 0.099 Uiso 1 1 d R U . . .
H8D H -0.0275 1.2200 0.2826 0.099 Uiso 1 1 d R U . . .
N1 N 0.1224(5) 0.4511(5) 0.6372(4) 0.0352(11) Uani 1 1 d . . . . .
H1 H 0.0743 0.5105 0.6738 0.042 Uiso 1 1 calc R U . . .
N2 N -0.2623(6) 0.2066(5) 1.0450(4) 0.0383(11) Uani 1 1 d . . . . .
C1 C 0.3872(8) 0.9055(6) 0.3353(5) 0.0382(13) Uani 1 1 d . . . . .
C2 C 0.3585(7) 0.7440(6) 0.3727(5) 0.0336(12) Uani 1 1 d . . . . .
C3 C 0.4397(7) 0.6662(6) 0.2974(5) 0.0351(13) Uani 1 1 d . . . . .
H3A H 0.5131 0.7148 0.2239 0.042 Uiso 1 1 calc R U . . .
C4 C 0.4110(7) 0.5170(6) 0.3319(5) 0.0317(12) Uani 1 1 d . . . . .
C5 C 0.3079(7) 0.4411(6) 0.4438(5) 0.0347(12) Uani 1 1 d . . . . .
H5A H 0.2926 0.3397 0.4678 0.042 Uiso 1 1 calc R U . . .
C6 C 0.2266(7) 0.5187(6) 0.5206(5) 0.0311(12) Uani 1 1 d . . . . .
C7 C 0.2521(7) 0.6699(5) 0.4833(5) 0.0332(12) Uani 1 1 d . . . . .
H7A H 0.1971 0.7220 0.5332 0.040 Uiso 1 1 calc R U . . .
C8 C 0.5023(7) 0.4297(6) 0.2529(5) 0.0387(13) Uani 1 1 d . . . . .
C9 C 0.0878(7) 0.3063(6) 0.6993(5) 0.0375(13) Uani 1 1 d . . . . .
C10 C -0.0260(7) 0.2716(6) 0.8241(5) 0.0346(12) Uani 1 1 d . . . . .
C11 C -0.1101(7) 0.1385(6) 0.8739(5) 0.0396(14) Uani 1 1 d . . . . .
H11A H -0.0872 0.0684 0.8345 0.048 Uiso 1 1 calc R U . . .
C12 C -0.2289(7) 0.1093(6) 0.9826(5) 0.0404(14) Uani 1 1 d . . . . .
H12A H -0.2871 0.0205 1.0135 0.048 Uiso 1 1 calc R U . . .
C13 C -0.1749(9) 0.3304(7) 0.9994(6) 0.0556(19) Uani 1 1 d . . . . .
H13A H -0.1937 0.3963 1.0434 0.067 Uiso 1 1 calc R U . . .
C14 C -0.0589(8) 0.3675(7) 0.8916(6) 0.0523(17) Uani 1 1 d . . . . .
H14A H -0.0022 0.4569 0.8636 0.063 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O4 1.920(4) 1_565 ?
Zn1 O1 1.931(4) . ?
Zn1 N2 2.045(4) 1_664 ?
Zn1 O7 2.237(5) . ?
Zn1 O6 2.258(4) . ?
O1 C1 1.265(6) . ?
O2 C1 1.253(6) . ?
O3 C9 1.219(6) . ?
O4 C8 1.257(6) . ?
O4 Zn1 1.920(4) 1_545 ?
O5 C8 1.227(6) . ?
O6 H6B 0.8500 . ?
O6 H6C 0.8500 . ?
O7 H7B 0.8501 . ?
O7 H7C 0.8500 . ?
O8 H8C 0.8500 . ?
O8 H8D 0.8500 . ?
N1 C9 1.346(6) . ?
N1 C6 1.407(6) . ?
N1 H1 0.8600 . ?
N2 C13 1.322(7) . ?
N2 C12 1.355(6) . ?
N2 Zn1 2.045(4) 1_446 ?
C1 C2 1.488(7) . ?
C2 C7 1.385(7) . ?
C2 C3 1.392(7) . ?
C3 C4 1.378(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.384(7) . ?
C4 C8 1.517(7) . ?
C5 C6 1.403(7) . ?
C5 H5A 0.9300 . ?
C6 C7 1.388(7) . ?
C7 H7A 0.9300 . ?
C9 C10 1.496(6) . ?
C10 C11 1.382(7) . ?
C10 C14 1.387(7) . ?
C11 C12 1.388(7) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.364(7) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Zn1 O1 127.43(16) 1_565 . ?
O4 Zn1 N2 128.81(17) 1_565 1_664 ?
O1 Zn1 N2 103.75(17) . 1_664 ?
O4 Zn1 O7 91.41(18) 1_565 . ?
O1 Zn1 O7 88.44(18) . . ?
N2 Zn1 O7 90.37(18) 1_664 . ?
O4 Zn1 O6 90.13(17) 1_565 . ?
O1 Zn1 O6 90.35(17) . . ?
N2 Zn1 O6 88.93(17) 1_664 . ?
O7 Zn1 O6 178.42(15) . . ?
C1 O1 Zn1 117.0(3) . . ?
C8 O4 Zn1 123.3(3) . 1_545 ?
Zn1 O6 H6B 109.8 . . ?
Zn1 O6 H6C 109.6 . . ?
H6B O6 H6C 108.2 . . ?
Zn1 O7 H7B 109.8 . . ?
Zn1 O7 H7C 109.8 . . ?
H7B O7 H7C 108.4 . . ?
H8C O8 H8D 108.1 . . ?
C9 N1 C6 128.9(4) . . ?
C9 N1 H1 115.6 . . ?
C6 N1 H1 115.6 . . ?
C13 N2 C12 117.3(4) . . ?
C13 N2 Zn1 121.6(4) . 1_446 ?
C12 N2 Zn1 121.0(3) . 1_446 ?
O2 C1 O1 122.4(5) . . ?
O2 C1 C2 120.7(5) . . ?
O1 C1 C2 116.9(5) . . ?
C7 C2 C3 119.6(5) . . ?
C7 C2 C1 120.2(5) . . ?
C3 C2 C1 120.2(5) . . ?
C4 C3 C2 119.9(5) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 121.0(5) . . ?
C3 C4 C8 120.5(5) . . ?
C5 C4 C8 118.4(5) . . ?
C4 C5 C6 119.4(5) . . ?
C4 C5 H5A 120.3 . . ?
C6 C5 H5A 120.3 . . ?
C7 C6 C5 119.3(5) . . ?
C7 C6 N1 117.0(4) . . ?
C5 C6 N1 123.7(5) . . ?
C2 C7 C6 120.8(5) . . ?
C2 C7 H7A 119.6 . . ?
C6 C7 H7A 119.6 . . ?
O5 C8 O4 124.6(5) . . ?
O5 C8 C4 119.5(5) . . ?
O4 C8 C4 115.8(5) . . ?
O3 C9 N1 124.3(5) . . ?
O3 C9 C10 120.6(5) . . ?
N1 C9 C10 115.0(5) . . ?
C11 C10 C14 117.0(5) . . ?
C11 C10 C9 118.8(5) . . ?
C14 C10 C9 124.2(5) . . ?
C10 C11 C12 120.0(5) . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
N2 C12 C11 121.8(5) . . ?
N2 C12 H12A 119.1 . . ?
C11 C12 H12A 119.1 . . ?
N2 C13 C14 124.0(5) . . ?
N2 C13 H13A 118.0 . . ?
C14 C13 H13A 118.0 . . ?
C13 C14 C10 119.8(5) . . ?
C13 C14 H14A 120.1 . . ?
C10 C14 H14A 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C1 O2 10.1(8) . . . . ?
Zn1 O1 C1 C2 -170.7(4) . . . . ?
O2 C1 C2 C7 0.0(9) . . . . ?
O1 C1 C2 C7 -179.2(5) . . . . ?
O2 C1 C2 C3 -179.4(6) . . . . ?
O1 C1 C2 C3 1.4(8) . . . . ?
C7 C2 C3 C4 1.2(8) . . . . ?
C1 C2 C3 C4 -179.4(5) . . . . ?
C2 C3 C4 C5 -2.6(9) . . . . ?
C2 C3 C4 C8 -178.4(5) . . . . ?
C3 C4 C5 C6 2.2(8) . . . . ?
C8 C4 C5 C6 178.0(5) . . . . ?
C4 C5 C6 C7 -0.4(8) . . . . ?
C4 C5 C6 N1 -178.6(5) . . . . ?
C9 N1 C6 C7 -174.8(5) . . . . ?
C9 N1 C6 C5 3.5(9) . . . . ?
C3 C2 C7 C6 0.5(8) . . . . ?
C1 C2 C7 C6 -178.9(5) . . . . ?
C5 C6 C7 C2 -1.0(8) . . . . ?
N1 C6 C7 C2 177.4(5) . . . . ?
Zn1 O4 C8 O5 -2.8(9) 1_545 . . . ?
Zn1 O4 C8 C4 176.3(4) 1_545 . . . ?
C3 C4 C8 O5 1.9(9) . . . . ?
C5 C4 C8 O5 -173.9(6) . . . . ?
C3 C4 C8 O4 -177.3(5) . . . . ?
C5 C4 C8 O4 6.9(8) . . . . ?
C6 N1 C9 O3 -2.9(10) . . . . ?
C6 N1 C9 C10 178.6(5) . . . . ?
O3 C9 C10 C11 -17.6(9) . . . . ?
N1 C9 C10 C11 161.0(5) . . . . ?
O3 C9 C10 C14 165.1(6) . . . . ?
N1 C9 C10 C14 -16.3(9) . . . . ?
C14 C10 C11 C12 3.5(9) . . . . ?
C9 C10 C11 C12 -174.0(5) . . . . ?
C13 N2 C12 C11 -1.0(9) . . . . ?
Zn1 N2 C12 C11 176.1(4) 1_446 . . . ?
C10 C11 C12 N2 -1.9(9) . . . . ?
C12 N2 C13 C14 2.3(10) . . . . ?
Zn1 N2 C13 C14 -174.8(6) 1_446 . . . ?
N2 C13 C14 C10 -0.7(12) . . . . ?
C11 C10 C14 C13 -2.3(10) . . . . ?
C9 C10 C14 C13 175.1(6) . . . . ?

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.095

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1936251'
loop_
_audit_author_name
_audit_author_address
'xiu mei zhang' 'Huaibei Normal University'
_audit_update_record             
;
2019-06-25 deposited with the CCDC.	2019-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 Cd N2 O11'
_chemical_formula_weight         504.72

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4640(7)
_cell_length_b                   10.1801(9)
_cell_length_c                   13.3769(11)
_cell_angle_alpha                70.6260(10)
_cell_angle_beta                 77.550(3)
_cell_angle_gamma                74.2340(10)
_cell_volume                     913.95(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    995
_cell_measurement_theta_min      2.858
_cell_measurement_theta_max      26.054

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.834
_exptl_crystal_F_000             508
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.258
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8845
_exptl_absorpt_correction_T_max  0.9632
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4603
_diffrn_reflns_av_unetI/netI     0.1372
_diffrn_reflns_av_R_equivalents  0.1070
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.863
_diffrn_reflns_theta_max         25.014
_diffrn_reflns_theta_full        25.014
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3154
_reflns_number_gt                2144
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1580P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3154
_refine_ls_number_parameters     253
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1405
_refine_ls_R_factor_gt           0.1106
_refine_ls_wR_factor_ref         0.2841
_refine_ls_wR_factor_gt          0.2684
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.28297(16) 0.78912(10) 0.91170(8) 0.0413(4) Uani 1 1 d . . . . .
N1 N 0.2637(17) 0.4797(11) 0.4919(8) 0.040(3) Uani 1 1 d . . . . .
H1 H 0.3110 0.4189 0.4563 0.048 Uiso 1 1 calc R U . . .
N2 N 0.2586(18) 0.7182(11) 0.0967(8) 0.045(3) Uani 1 1 d . . . . .
O1 O 0.2547(16) 0.0332(9) 0.9200(7) 0.050(3) Uani 1 1 d . . . . .
O2 O 0.3123(16) -0.0067(10) 0.7628(8) 0.056(3) Uani 1 1 d . . . . .
O3 O 0.2819(15) 0.5196(10) 0.9323(7) 0.049(3) Uani 1 1 d . . . . .
O4 O 0.2909(14) 0.6914(9) 0.7780(7) 0.043(2) Uani 1 1 d . . . . .
O5 O 0.109(2) 0.7095(12) 0.4788(8) 0.073(4) Uani 1 1 d . . . . .
O6 O 0.5933(16) 0.7305(13) 0.9209(8) 0.067(3) Uani 1 1 d . . . . .
H6C H 0.6360 0.6526 0.9660 0.080 Uiso 1 1 d R U . . .
H6D H 0.6797 0.7486 0.8686 0.080 Uiso 1 1 d DR U . . .
O7 O -0.0359(16) 0.8417(13) 0.9280(10) 0.071(3) Uani 1 1 d . . . . .
H7C H -0.1206 0.8830 0.9681 0.085 Uiso 1 1 d R U . . .
H7D H -0.0851 0.8376 0.8777 0.085 Uiso 1 1 d R U . . .
O8 O 0.5499(19) 0.7572(13) 0.5934(10) 0.082(4) Uani 1 1 d . . . . .
H8C H 0.4716 0.7371 0.6496 0.099 Uiso 1 1 d R U . . .
H8D H 0.5828 0.8323 0.5903 0.099 Uiso 1 1 d R U . . .
O9 O 0.867(2) 0.8085(19) 0.7292(13) 0.140(8) Uani 1 1 d . . . . .
H9C H 0.9598 0.8488 0.7030 0.168 Uiso 1 1 d R U . . .
H9D H 0.7786 0.8552 0.6922 0.168 Uiso 1 1 d DR U . . .
O10 O 0.100(3) 0.0001(19) 0.6024(15) 0.132(6) Uani 1 1 d . U . . .
H10C H 0.1618 -0.0015 0.6494 0.158 Uiso 1 1 d R U . . .
H10D H 0.0390 0.0850 0.5784 0.158 Uiso 1 1 d R U . . .
O11 O 0.660(4) 0.008(3) 0.588(2) 0.187(11) Uani 1 1 d . . . . .
H11C H 0.5795 0.0755 0.5534 0.224 Uiso 1 1 d R U . . .
H11D H 0.7524 -0.0141 0.5422 0.224 Uiso 1 1 d R U . . .
C1 C 0.281(2) 0.0780(14) 0.8191(11) 0.045(3) Uani 1 1 d . . . . .
C2 C 0.2783(18) 0.5636(14) 0.8325(11) 0.039(3) Uani 1 1 d . . . . .
C3 C 0.2779(19) 0.2320(12) 0.7640(10) 0.035(3) Uani 1 1 d . . . . .
C4 C 0.2720(19) 0.3243(13) 0.8255(10) 0.035(3) Uani 1 1 d . . . . .
H4 H 0.2660 0.2903 0.8996 0.042 Uiso 1 1 calc R U . . .
C5 C 0.2756(19) 0.4665(12) 0.7716(10) 0.035(3) Uani 1 1 d . . . . .
C6 C 0.2651(19) 0.5203(13) 0.6632(11) 0.039(3) Uani 1 1 d . . . . .
H6 H 0.2565 0.6173 0.6293 0.046 Uiso 1 1 calc R U . . .
C7 C 0.2675(19) 0.4295(13) 0.6046(10) 0.037(3) Uani 1 1 d . . . . .
C8 C 0.272(2) 0.2872(15) 0.6549(11) 0.045(3) Uani 1 1 d . . . . .
H8 H 0.2709 0.2275 0.6154 0.054 Uiso 1 1 calc R U . . .
C9 C 0.192(2) 0.6139(15) 0.4370(11) 0.044(3) Uani 1 1 d . . . . .
C10 C 0.272(2) 0.8088(15) 0.1461(11) 0.052(4) Uani 1 1 d . . . . .
H10 H 0.2958 0.8977 0.1050 0.062 Uiso 1 1 calc R U . . .
C11 C 0.253(2) 0.7746(15) 0.2566(12) 0.052(4) Uani 1 1 d . . . . .
H11 H 0.2645 0.8386 0.2896 0.062 Uiso 1 1 calc R U . . .
C12 C 0.2173(19) 0.6463(13) 0.3147(10) 0.038(3) Uani 1 1 d . . . . .
C13 C 0.195(2) 0.5539(14) 0.2678(11) 0.047(4) Uani 1 1 d . . . . .
H13 H 0.1660 0.4662 0.3077 0.057 Uiso 1 1 calc R U . . .
C14 C 0.216(2) 0.5970(13) 0.1573(11) 0.044(3) Uani 1 1 d . . . . .
H14 H 0.1993 0.5357 0.1234 0.053 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 O6 2.250(12) . ?
Cd1 O7 2.271(12) . ?
Cd1 O4 2.301(9) . ?
Cd1 N2 2.318(10) 1_556 ?
Cd1 O2 2.377(10) 1_565 ?
Cd1 O1 2.474(9) 1_565 ?
Cd1 O3 2.667(9) . ?
N1 C9 1.340(17) . ?
N1 C7 1.426(16) . ?
N1 H1 0.8600 . ?
N2 C14 1.310(16) . ?
N2 C10 1.335(18) . ?
N2 Cd1 2.318(10) 1_554 ?
O1 C1 1.263(17) . ?
O1 Cd1 2.474(9) 1_545 ?
O2 C1 1.269(17) . ?
O2 Cd1 2.377(10) 1_545 ?
O3 C2 1.264(17) . ?
O4 C2 1.281(15) . ?
O5 C9 1.236(18) . ?
O6 H6C 0.8500 . ?
O6 H6D 0.8501 . ?
O7 H7C 0.8500 . ?
O7 H7D 0.8500 . ?
O8 H8C 0.8500 . ?
O8 H8D 0.8501 . ?
O9 H9C 0.8501 . ?
O9 H9D 0.8500 . ?
O10 H10C 0.8501 . ?
O10 H10D 0.8500 . ?
O11 H11C 0.8500 . ?
O11 H11D 0.8499 . ?
C1 C3 1.491(17) . ?
C2 C5 1.481(17) . ?
C3 C8 1.384(19) . ?
C3 C4 1.427(17) . ?
C4 C5 1.392(16) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(18) . ?
C6 C7 1.391(18) . ?
C6 H6 0.9300 . ?
C7 C8 1.375(18) . ?
C8 H8 0.9300 . ?
C9 C12 1.538(19) . ?
C10 C11 1.39(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.344(19) . ?
C11 H11 0.9300 . ?
C12 C13 1.354(19) . ?
C13 C14 1.382(19) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Cd1 O7 171.9(4) . . ?
O6 Cd1 O4 97.8(4) . . ?
O7 Cd1 O4 88.7(4) . . ?
O6 Cd1 N2 83.4(4) . 1_556 ?
O7 Cd1 N2 88.5(4) . 1_556 ?
O4 Cd1 N2 138.1(3) . 1_556 ?
O6 Cd1 O2 92.3(4) . 1_565 ?
O7 Cd1 O2 93.5(4) . 1_565 ?
O4 Cd1 O2 81.6(3) . 1_565 ?
N2 Cd1 O2 140.3(4) 1_556 1_565 ?
O6 Cd1 O1 92.4(4) . 1_565 ?
O7 Cd1 O1 86.4(4) . 1_565 ?
O4 Cd1 O1 134.8(3) . 1_565 ?
N2 Cd1 O1 86.7(3) 1_556 1_565 ?
O2 Cd1 O1 54.0(3) 1_565 1_565 ?
O6 Cd1 O3 91.0(4) . . ?
O7 Cd1 O3 89.1(4) . . ?
O4 Cd1 O3 52.5(3) . . ?
N2 Cd1 O3 85.6(3) 1_556 . ?
O2 Cd1 O3 134.0(3) 1_565 . ?
O1 Cd1 O3 171.2(3) 1_565 . ?
C9 N1 C7 125.3(11) . . ?
C9 N1 H1 117.4 . . ?
C7 N1 H1 117.4 . . ?
C14 N2 C10 117.2(12) . . ?
C14 N2 Cd1 123.3(9) . 1_554 ?
C10 N2 Cd1 119.2(9) . 1_554 ?
C1 O1 Cd1 90.3(8) . 1_545 ?
C1 O2 Cd1 94.7(8) . 1_545 ?
C2 O3 Cd1 84.5(8) . . ?
C2 O4 Cd1 101.1(8) . . ?
Cd1 O6 H6C 117.8 . . ?
Cd1 O6 H6D 125.9 . . ?
H6C O6 H6D 108.5 . . ?
Cd1 O7 H7C 132.5 . . ?
Cd1 O7 H7D 117.2 . . ?
H7C O7 H7D 108.7 . . ?
H8C O8 H8D 108.4 . . ?
H9C O9 H9D 107.7 . . ?
H10C O10 H10D 108.4 . . ?
H11C O11 H11D 107.8 . . ?
O1 C1 O2 121.0(12) . . ?
O1 C1 C3 120.2(12) . . ?
O2 C1 C3 118.8(12) . . ?
O3 C2 O4 121.6(12) . . ?
O3 C2 C5 121.5(12) . . ?
O4 C2 C5 116.7(12) . . ?
C8 C3 C4 119.9(11) . . ?
C8 C3 C1 120.7(12) . . ?
C4 C3 C1 119.3(11) . . ?
C5 C4 C3 118.1(11) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C6 C5 C4 120.9(11) . . ?
C6 C5 C2 119.5(11) . . ?
C4 C5 C2 119.5(11) . . ?
C5 C6 C7 120.0(11) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.3(12) . . ?
C8 C7 N1 117.9(12) . . ?
C6 C7 N1 121.9(11) . . ?
C3 C8 C7 120.4(13) . . ?
C3 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
O5 C9 N1 124.1(13) . . ?
O5 C9 C12 119.7(12) . . ?
N1 C9 C12 116.2(12) . . ?
N2 C10 C11 122.0(13) . . ?
N2 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C12 C11 C10 118.2(14) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C11 C12 C13 121.5(13) . . ?
C11 C12 C9 116.5(13) . . ?
C13 C12 C9 121.9(12) . . ?
C12 C13 C14 116.3(12) . . ?
C12 C13 H13 121.9 . . ?
C14 C13 H13 121.9 . . ?
N2 C14 C13 124.7(13) . . ?
N2 C14 H14 117.7 . . ?
C13 C14 H14 117.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cd1 O1 C1 O2 -1.8(16) 1_545 . . . ?
Cd1 O1 C1 C3 178.6(13) 1_545 . . . ?
Cd1 O2 C1 O1 1.8(16) 1_545 . . . ?
Cd1 O2 C1 C3 -178.5(12) 1_545 . . . ?
Cd1 O3 C2 O4 5.1(12) . . . . ?
Cd1 O3 C2 C5 179.9(12) . . . . ?
Cd1 O4 C2 O3 -6.0(15) . . . . ?
Cd1 O4 C2 C5 178.9(10) . . . . ?
O1 C1 C3 C8 -167.9(14) . . . . ?
O2 C1 C3 C8 12(2) . . . . ?
O1 C1 C3 C4 9(2) . . . . ?
O2 C1 C3 C4 -170.5(13) . . . . ?
C8 C3 C4 C5 -5(2) . . . . ?
C1 C3 C4 C5 177.8(12) . . . . ?
C3 C4 C5 C6 7(2) . . . . ?
C3 C4 C5 C2 -177.2(12) . . . . ?
O3 C2 C5 C6 177.8(13) . . . . ?
O4 C2 C5 C6 -7.2(19) . . . . ?
O3 C2 C5 C4 2(2) . . . . ?
O4 C2 C5 C4 176.7(12) . . . . ?
C4 C5 C6 C7 -6(2) . . . . ?
C2 C5 C6 C7 178.3(12) . . . . ?
C5 C6 C7 C8 3(2) . . . . ?
C5 C6 C7 N1 -177.7(12) . . . . ?
C9 N1 C7 C8 154.2(14) . . . . ?
C9 N1 C7 C6 -25(2) . . . . ?
C4 C3 C8 C7 2(2) . . . . ?
C1 C3 C8 C7 179.6(13) . . . . ?
C6 C7 C8 C3 -1(2) . . . . ?
N1 C7 C8 C3 179.3(13) . . . . ?
C7 N1 C9 O5 -5(2) . . . . ?
C7 N1 C9 C12 175.5(12) . . . . ?
C14 N2 C10 C11 3(2) . . . . ?
Cd1 N2 C10 C11 177.9(12) 1_554 . . . ?
N2 C10 C11 C12 -1(3) . . . . ?
C10 C11 C12 C13 -2(2) . . . . ?
C10 C11 C12 C9 -178.7(14) . . . . ?
O5 C9 C12 C11 38(2) . . . . ?
N1 C9 C12 C11 -142.3(14) . . . . ?
O5 C9 C12 C13 -138.4(16) . . . . ?
N1 C9 C12 C13 41(2) . . . . ?
C11 C12 C13 C14 2(2) . . . . ?
C9 C12 C13 C14 178.4(13) . . . . ?
C10 N2 C14 C13 -4(2) . . . . ?
Cd1 N2 C14 C13 -177.8(12) 1_554 . . . ?
C12 C13 C14 N2 1(2) . . . . ?

_refine_diff_density_max         2.179
_refine_diff_density_min         -1.286
_refine_diff_density_rms         0.267

