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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_HL1
_database_code_depnum_ccdc_archive 'CCDC 1976443'
loop_
_audit_author_name
_audit_author_address
'XiuFang Mu'
;zhongnandaxue
China
;
_audit_update_record             
;
2020-06-23 deposited with the CCDC.	2020-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N3 O'
_chemical_formula_weight         237.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.3807(4)
_cell_length_b                   10.4296(4)
_cell_length_c                   11.1541(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1207.62(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2856
_cell_measurement_theta_min      1.86
_cell_measurement_theta_max      28.56

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   0.1856
_exptl_transmission_factor_max   0.5622
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6965
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16653
_diffrn_reflns_av_unetI/netI     0.0089
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.674
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2365
_reflns_number_gt                2210
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0415P)²+0.0940P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 896 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2365
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0740
_refine_ls_wR_factor_gt          0.0722
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.03945(12) 0.68435(11) 0.32695(10) 0.0533(3) Uani 1 1 d . . . . .
N2 N 0.12934(13) 0.55467(13) 0.50714(12) 0.0465(3) Uani 1 1 d . . . . .
H2 H 0.0770 0.5444 0.4481 0.056 Uiso 1 1 calc R U . . .
N1 N 0.10789(13) 0.78491(13) 0.36063(12) 0.0453(3) Uani 1 1 d . . . . .
N3 N 0.02341(15) 0.31465(14) 0.48845(14) 0.0550(4) Uani 1 1 d . . . . .
C5 C 0.18873(15) 0.77921(16) 0.45751(15) 0.0463(4) Uani 1 1 d . . . . .
C10 C 0.09035(15) 0.34095(17) 0.58804(15) 0.0494(4) Uani 1 1 d . . . . .
C6 C 0.19782(15) 0.66359(16) 0.52812(15) 0.0468(4) Uani 1 1 d . . . . .
C1 C 0.09619(18) 0.89452(17) 0.29582(16) 0.0541(4) Uani 1 1 d . . . . .
H1 H 0.0406 0.8962 0.2304 0.065 Uiso 1 1 calc R U . . .
C8 C 0.24377(18) 0.51744(19) 0.66903(16) 0.0581(5) Uani 1 1 d . . . . .
H8 H 0.2795 0.4773 0.7356 0.070 Uiso 1 1 calc R U . . .
C9 C 0.15448(16) 0.46442(17) 0.59165(15) 0.0484(4) Uani 1 1 d . . . . .
C2 C 0.1639(2) 1.00187(19) 0.32434(19) 0.0638(5) Uani 1 1 d . . . . .
H2A H 0.1530 1.0766 0.2800 0.077 Uiso 1 1 calc R U . . .
C3 C 0.2488(2) 0.9992(2) 0.4195(2) 0.0687(5) Uani 1 1 d . . . . .
H3 H 0.2970 1.0713 0.4394 0.082 Uiso 1 1 calc R U . . .
C4 C 0.26040(19) 0.88835(18) 0.48368(17) 0.0609(5) Uani 1 1 d . . . . .
H4 H 0.3183 0.8857 0.5472 0.073 Uiso 1 1 calc R U . . .
C14 C -0.0391(2) 0.20338(19) 0.4840(2) 0.0648(5) Uani 1 1 d . . . . .
H14 H -0.0852 0.1843 0.4147 0.078 Uiso 1 1 calc R U . . .
C7 C 0.27088(18) 0.64088(19) 0.63024(16) 0.0580(5) Uani 1 1 d . . . . .
H7 H 0.3277 0.6981 0.6661 0.070 Uiso 1 1 calc R U . . .
C12 C 0.0288(2) 0.1423(3) 0.6764(2) 0.0872(8) Uani 1 1 d . . . . .
H12 H 0.0309 0.0842 0.7397 0.105 Uiso 1 1 calc R U . . .
C11 C 0.0947(2) 0.2561(2) 0.6836(2) 0.0737(6) Uani 1 1 d . . . . .
H11 H 0.1418 0.2761 0.7521 0.088 Uiso 1 1 calc R U . . .
C13 C -0.0399(2) 0.1152(2) 0.5749(2) 0.0761(6) Uani 1 1 d . . . . .
H13 H -0.0860 0.0390 0.5679 0.091 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.3212(17) . ?
N2 C9 1.357(2) . ?
N2 C6 1.360(2) . ?
N2 H2 0.8600 . ?
N1 C1 1.358(2) . ?
N1 C5 1.370(2) . ?
N3 C14 1.331(2) . ?
N3 C10 1.339(2) . ?
C5 C4 1.391(2) . ?
C5 C6 1.443(2) . ?
C10 C11 1.387(3) . ?
C10 C9 1.450(2) . ?
C6 C7 1.389(2) . ?
C1 C2 1.360(3) . ?
C1 H1 0.9300 . ?
C8 C9 1.382(3) . ?
C8 C7 1.387(3) . ?
C8 H8 0.9300 . ?
C2 C3 1.380(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.366(3) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C14 C13 1.369(3) . ?
C14 H14 0.9300 . ?
C7 H7 0.9300 . ?
C12 C13 1.368(3) . ?
C12 C11 1.372(3) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C13 H13 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
C9 N2 C6 111.05(13) . . ?
C9 N2 H2 124.5 . . ?
C6 N2 H2 124.5 . . ?
O1 N1 C1 117.96(13) . . ?
O1 N1 C5 121.29(13) . . ?
C1 N1 C5 120.75(14) . . ?
C14 N3 C10 117.59(16) . . ?
N1 C5 C4 117.25(16) . . ?
N1 C5 C6 120.46(15) . . ?
C4 C5 C6 122.29(15) . . ?
N3 C10 C11 121.61(18) . . ?
N3 C10 C9 116.31(15) . . ?
C11 C10 C9 122.05(17) . . ?
N2 C6 C7 106.50(15) . . ?
N2 C6 C5 124.72(14) . . ?
C7 C6 C5 128.73(16) . . ?
N1 C1 C2 121.50(17) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C9 C8 C7 108.22(16) . . ?
C9 C8 H8 125.9 . . ?
C7 C8 H8 125.9 . . ?
N2 C9 C8 106.57(16) . . ?
N2 C9 C10 120.55(15) . . ?
C8 C9 C10 132.89(17) . . ?
C1 C2 C3 119.59(18) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 H2A 120.2 . . ?
C4 C3 C2 118.46(19) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 122.39(18) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
N3 C14 C13 124.1(2) . . ?
N3 C14 H14 117.9 . . ?
C13 C14 H14 117.9 . . ?
C8 C7 C6 107.66(16) . . ?
C8 C7 H7 126.2 . . ?
C6 C7 H7 126.2 . . ?
C13 C12 C11 119.2(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C11 C10 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C12 C13 C14 118.1(2) . . ?
C12 C13 H13 121.0 . . ?
C14 C13 H13 121.0 . . ?

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
O1 N1 C5 C4 177.74(15) . . . . ?
C1 N1 C5 C4 -2.0(2) . . . . ?
O1 N1 C5 C6 -2.1(2) . . . . ?
C1 N1 C5 C6 178.15(15) . . . . ?
C14 N3 C10 C11 -0.2(3) . . . . ?
C14 N3 C10 C9 -178.32(16) . . . . ?
C9 N2 C6 C7 0.59(18) . . . . ?
C9 N2 C6 C5 -177.32(15) . . . . ?
N1 C5 C6 N2 -0.7(2) . . . . ?
C4 C5 C6 N2 179.45(16) . . . . ?
N1 C5 C6 C7 -178.10(16) . . . . ?
C4 C5 C6 C7 2.0(3) . . . . ?
O1 N1 C1 C2 -179.64(16) . . . . ?
C5 N1 C1 C2 0.1(3) . . . . ?
C6 N2 C9 C8 -0.66(19) . . . . ?
C6 N2 C9 C10 179.03(15) . . . . ?
C7 C8 C9 N2 0.5(2) . . . . ?
C7 C8 C9 C10 -179.17(18) . . . . ?
N3 C10 C9 N2 10.4(2) . . . . ?
C11 C10 C9 N2 -167.71(17) . . . . ?
N3 C10 C9 C8 -169.96(18) . . . . ?
C11 C10 C9 C8 11.9(3) . . . . ?
N1 C1 C2 C3 1.5(3) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
N1 C5 C4 C3 2.4(3) . . . . ?
C6 C5 C4 C3 -177.75(19) . . . . ?
C10 N3 C14 C13 0.5(3) . . . . ?
C9 C8 C7 C6 -0.1(2) . . . . ?
N2 C6 C7 C8 -0.28(19) . . . . ?
C5 C6 C7 C8 177.52(17) . . . . ?
C13 C12 C11 C10 -0.1(4) . . . . ?
N3 C10 C11 C12 0.0(3) . . . . ?
C9 C10 C11 C12 178.0(2) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
N3 C14 C13 C12 -0.7(4) . . . . ?

_refine_diff_density_max         0.106
_refine_diff_density_min         -0.100
_refine_diff_density_rms         0.020

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_Zn(L2)2
_database_code_depnum_ccdc_archive 'CCDC 1976446'
loop_
_audit_author_name
_audit_author_address
'XiuFang Mu'
;zhongnandaxue
China
;
_audit_update_record             
;
2020-06-23 deposited with the CCDC.	2020-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H28 Cl8 N6 O4 Zn'
_chemical_formula_weight         909.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/4, -y+1/4, z'
'x, -y+1/4, -z+1/4'
'-x+1/4, y, -z+1/4'
'x, y+1/2, z+1/2'
'-x+1/4, -y+3/4, z+1/2'
'x, -y+3/4, -z+3/4'
'-x+1/4, y+1/2, -z+3/4'
'x+1/2, y, z+1/2'
'-x+3/4, -y+1/4, z+1/2'
'x+1/2, -y+1/4, -z+3/4'
'-x+3/4, y, -z+3/4'
'x+1/2, y+1/2, z'
'-x+3/4, -y+3/4, z'
'x+1/2, -y+3/4, -z+1/4'
'-x+3/4, y+1/2, -z+1/4'
'-x, -y, -z'
'x-1/4, y-1/4, -z'
'-x, y-1/4, z-1/4'
'x-1/4, -y, z-1/4'
'-x, -y+1/2, -z+1/2'
'x-1/4, y+1/4, -z+1/2'
'-x, y+1/4, z+1/4'
'x-1/4, -y+1/2, z+1/4'
'-x+1/2, -y, -z+1/2'
'x+1/4, y-1/4, -z+1/2'
'-x+1/2, y-1/4, z+1/4'
'x+1/4, -y, z+1/4'
'-x+1/2, -y+1/2, -z'
'x+1/4, y+1/4, -z'
'-x+1/2, y+1/4, z-1/4'
'x+1/4, -y+1/2, z-1/4'

_cell_length_a                   12.8301(9)
_cell_length_b                   16.4771(11)
_cell_length_c                   37.538(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7935.6(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2856
_cell_measurement_theta_min      1.82
_cell_measurement_theta_max      28.56

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_F_000             3680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    1.201
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6073
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   
'SADABS-2008/1 - Bruker AXS was used for absorption correction. wR2(int) was 0.0672 before and 0.0527 after correction. The Ratio of minimum to maximum transmission is 0.8148. The  Lambda/2 correction factor is 0.0015.'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14968
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_av_R_equivalents  0.1023
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.084
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             1757
_reflns_number_gt                899
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1000P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1757
_refine_ls_number_parameters     127
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1575
_refine_ls_R_factor_gt           0.0783
_refine_ls_wR_factor_ref         0.2155
_refine_ls_wR_factor_gt          0.1904
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.162
_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
Zn1 Zn 0.3750 0.8750 0.3750 0.0641(6) Uani 1 4 d S T P . .
O1 O 0.2571(3) 0.7828(3) 0.38227(11) 0.0769(13) Uani 1 1 d . . . . .
N1 N 0.3750 0.8750 0.42714(18) 0.0626(18) Uani 1 2 d S T P . .
N2 N 0.2809(4) 0.7206(4) 0.40294(16) 0.0723(14) Uani 1 1 d . . . . .
C1 C 0.3523(4) 0.8114(4) 0.44911(16) 0.0697(17) Uani 1 1 d . . . . .
C2 C 0.3277(5) 0.7307(4) 0.43541(19) 0.0694(17) Uani 1 1 d . . . . .
C5 C 0.3617(5) 0.8348(4) 0.48409(17) 0.087(2) Uani 1 1 d . . . . .
H5 H 0.3518 0.8022 0.5040 0.105 Uiso 1 1 calc R U . . .
C6 C 0.2562(5) 0.6465(5) 0.3907(2) 0.093(2) Uani 1 1 d . . . . .
H6 H 0.2269 0.6410 0.3681 0.111 Uiso 1 1 calc R U . . .
C7 C 0.3489(6) 0.6617(6) 0.4557(2) 0.093(2) Uani 1 1 d . . . . .
H7 H 0.3818 0.6667 0.4777 0.112 Uiso 1 1 calc R U . . .
C11 C 0.3210(7) 0.5859(6) 0.4432(3) 0.106(3) Uani 1 1 d . . . . .
H11 H 0.3345 0.5400 0.4569 0.128 Uiso 1 1 calc R U . . .
C13 C 0.2740(7) 0.5785(5) 0.4111(3) 0.111(3) Uani 1 1 d . . . . .
H13 H 0.2538 0.5277 0.4029 0.133 Uiso 1 1 calc R U . . .
Cl1 Cl 0.1134(3) 0.7240(2) 0.29628(12) 0.2056(16) Uani 1 1 d . . . . .
Cl2 Cl 0.0192(5) 0.8748(4) 0.3008(2) 0.175(3) Uani 0.705(13) 1 d . . P A 1
C3 C 0.1226(6) 0.8197(5) 0.3127(3) 0.124(3) Uani 1 1 d . . . . .
H3AA H 0.1271 0.8176 0.3385 0.149 Uiso 0.705(13) 1 calc R U P A 1
H3AB H 0.1856 0.8451 0.3038 0.149 Uiso 0.705(13) 1 calc R U P A 1
H3BC H 0.1371 0.8574 0.2935 0.149 Uiso 0.295(13) 1 calc R U P A 2
H3BD H 0.1796 0.8226 0.3297 0.149 Uiso 0.295(13) 1 calc R U P A 2
Cl2A Cl -0.0016(8) 0.8481(7) 0.3351(7) 0.174(8) Uani 0.295(13) 1 d . U P A 2


_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 N1 1.957(7) 7_565 ?
Zn1 N1 1.957(7) . ?
Zn1 O1 2.161(4) . ?
Zn1 O1 2.161(4) 14_565 ?
Zn1 O1 2.161(4) 7_565 ?
Zn1 O1 2.161(4) 12 ?
O1 N2 1.322(6) . ?
N1 C1 1.364(7) . ?
N1 C1 1.364(7) 14_565 ?
N2 C6 1.343(8) . ?
N2 C2 1.369(8) . ?
C1 C5 1.374(8) . ?
C1 C2 1.461(9) . ?
C2 C7 1.396(9) . ?
C5 C5 1.366(14) 14_565 ?
C5 H5 0.9300 . ?
C6 C13 1.377(10) . ?
C6 H6 0.9300 . ?
C7 C11 1.381(11) . ?
C7 H7 0.9300 . ?
C11 C13 1.354(11) . ?
C11 H11 0.9300 . ?
C13 H13 0.9300 . ?
Cl1 C3 1.698(9) . ?
Cl2 C3 1.669(9) . ?
C3 Cl2A 1.861(17) . ?
C3 H3AA 0.9700 . ?
C3 H3AB 0.9700 . ?
C3 H3BC 0.9700 . ?
C3 H3BD 0.9700 . ?

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 Zn1 N1 180.0 7_565 . ?
N1 Zn1 O1 97.25(11) 7_565 . ?
N1 Zn1 O1 82.75(11) . . ?
N1 Zn1 O1 97.25(11) 7_565 14_565 ?
N1 Zn1 O1 82.75(11) . 14_565 ?
O1 Zn1 O1 165.5(2) . 14_565 ?
N1 Zn1 O1 82.75(11) 7_565 7_565 ?
N1 Zn1 O1 97.25(11) . 7_565 ?
O1 Zn1 O1 91.1(2) . 7_565 ?
O1 Zn1 O1 90.7(2) 14_565 7_565 ?
N1 Zn1 O1 82.75(11) 7_565 12 ?
N1 Zn1 O1 97.25(11) . 12 ?
O1 Zn1 O1 90.7(2) . 12 ?
O1 Zn1 O1 91.1(2) 14_565 12 ?
O1 Zn1 O1 165.5(2) 7_565 12 ?
N2 O1 Zn1 117.2(3) . . ?
C1 N1 C1 105.6(8) . 14_565 ?
C1 N1 Zn1 127.2(4) . . ?
C1 N1 Zn1 127.2(4) 14_565 . ?
O1 N2 C6 116.7(6) . . ?
O1 N2 C2 122.0(6) . . ?
C6 N2 C2 121.3(6) . . ?
N1 C1 C5 110.1(7) . . ?
N1 C1 C2 122.2(6) . . ?
C5 C1 C2 127.7(6) . . ?
N2 C2 C7 118.2(7) . . ?
N2 C2 C1 121.3(6) . . ?
C7 C2 C1 120.5(7) . . ?
C5 C5 C1 107.1(4) 14_565 . ?
C5 C5 H5 126.5 14_565 . ?
C1 C5 H5 126.5 . . ?
N2 C6 C13 120.6(8) . . ?
N2 C6 H6 119.7 . . ?
C13 C6 H6 119.7 . . ?
C11 C7 C2 120.1(8) . . ?
C11 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C13 C11 C7 119.9(8) . . ?
C13 C11 H11 120.0 . . ?
C7 C11 H11 120.0 . . ?
C11 C13 C6 119.9(8) . . ?
C11 C13 H13 120.1 . . ?
C6 C13 H13 120.1 . . ?
Cl2 C3 Cl1 110.6(5) . . ?
Cl1 C3 Cl2A 109.8(6) . . ?
Cl2 C3 H3AA 109.5 . . ?
Cl1 C3 H3AA 109.5 . . ?
Cl2 C3 H3AB 109.5 . . ?
Cl1 C3 H3AB 109.5 . . ?
H3AA C3 H3AB 108.1 . . ?
Cl1 C3 H3BC 109.7 . . ?
Cl2A C3 H3BC 109.7 . . ?
Cl1 C3 H3BD 109.7 . . ?
Cl2A C3 H3BD 109.7 . . ?
H3BC C3 H3BD 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 N2 C6 -134.3(5) . . . . ?
Zn1 O1 N2 C2 46.2(6) . . . . ?
C1 N1 C1 C5 -0.6(3) 14_565 . . . ?
Zn1 N1 C1 C5 179.4(3) . . . . ?
C1 N1 C1 C2 -177.6(7) 14_565 . . . ?
Zn1 N1 C1 C2 2.4(7) . . . . ?
O1 N2 C2 C7 179.1(5) . . . . ?
C6 N2 C2 C7 -0.3(9) . . . . ?
O1 N2 C2 C1 0.9(8) . . . . ?
C6 N2 C2 C1 -178.6(6) . . . . ?
N1 C1 C2 N2 -29.8(8) . . . . ?
C5 C1 C2 N2 153.7(6) . . . . ?
N1 C1 C2 C7 152.0(5) . . . . ?
C5 C1 C2 C7 -24.5(9) . . . . ?
N1 C1 C5 C5 1.5(9) . . . 14_565 ?
C2 C1 C5 C5 178.3(7) . . . 14_565 ?
O1 N2 C6 C13 -177.1(6) . . . . ?
C2 N2 C6 C13 2.4(10) . . . . ?
N2 C2 C7 C11 -1.2(9) . . . . ?
C1 C2 C7 C11 177.1(6) . . . . ?
C2 C7 C11 C13 0.6(11) . . . . ?
C7 C11 C13 C6 1.5(12) . . . . ?
N2 C6 C13 C11 -3.0(12) . . . . ?

_refine_diff_density_max         0.480
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.074

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_Zn(L1)2
_database_code_depnum_ccdc_archive 'CCDC 1976445'
loop_
_audit_author_name
_audit_author_address
'XiuFang Mu'
;zhongnandaxue
China
;
_audit_update_record             
;
2020-06-23 deposited with the CCDC.	2020-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C56.50 H42 Cl N12 O4 Zn2'
_chemical_formula_weight         1119.21

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   31.092(3)
_cell_length_b                   17.2866(16)
_cell_length_c                   9.3852(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.426(6)
_cell_angle_gamma                90
_cell_volume                     5039.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2856
_cell_measurement_theta_min      1.85
_cell_measurement_theta_max      28.56

_exptl_crystal_description       PLATE
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             2296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.067
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6073
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   
'SADABS-2008/1 - Bruker AXS was used for absorption correction. wR2(int) was 0.0672 before and 0.0527 after correction. The Ratio of minimum to maximum transmission is 0.8148. The  Lambda/2 correction factor is 0.0015.'


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18752
_diffrn_reflns_av_unetI/netI     0.1587
_diffrn_reflns_av_R_equivalents  0.0922
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.356
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             4426
_reflns_number_gt                1755
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0894P)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         4426
_refine_ls_number_parameters     348
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.2148
_refine_ls_R_factor_gt           0.0703
_refine_ls_wR_factor_ref         0.1806
_refine_ls_wR_factor_gt          0.1489
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_restrained_S_all      0.925
_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
Zn1 Zn -0.35681(3) -0.20168(4) -0.70479(8) 0.0639(4) Uani 1 1 d . . . . .
O1 O -0.32511(19) -0.2006(3) -0.9007(5) 0.113(2) Uani 1 1 d . . . . .
O2 O -0.29690(14) -0.1717(3) -0.6043(5) 0.0904(16) Uani 1 1 d . . . . .
N1 N -0.31937(18) -0.2531(4) -0.9965(7) 0.0740(16) Uani 1 1 d . . . . .
N2 N -0.35890(16) -0.3149(3) -0.7394(6) 0.0610(15) Uani 1 1 d . . . . .
N3 N -0.38380(17) -0.2480(3) -0.5034(5) 0.0686(16) Uani 1 1 d . . . . .
N4 N -0.42450(19) -0.1860(4) -0.8286(6) 0.0719(16) Uani 1 1 d . . . . .
N5 N -0.37228(19) -0.0932(3) -0.6778(5) 0.0585(14) Uani 1 1 d . . . . .
N6 N -0.2891(2) -0.1139(4) -0.5178(6) 0.0654(15) Uani 1 1 d . . . . .
C29 C -0.3003(3) -0.2278(5) -1.1139(9) 0.101(3) Uani 1 1 d . . . . .
H29 H -0.2910 -0.1768 -1.1176 0.122 Uiso 1 1 calc R U . . .
C2 C -0.2942(3) -0.2748(6) -1.2268(11) 0.142(4) Uani 1 1 d . . . . .
H2 H -0.2814 -0.2567 -1.3080 0.171 Uiso 1 1 calc R U . . .
C30 C -0.3078(4) -0.3509(6) -1.2169(11) 0.144(4) Uani 1 1 d . . . . .
H30 H -0.3052 -0.3845 -1.2934 0.173 Uiso 1 1 calc R U . . .
C4 C -0.3249(3) -0.3756(4) -1.0961(9) 0.111(3) Uani 1 1 d . . . . .
H4 H -0.3328 -0.4274 -1.0899 0.133 Uiso 1 1 calc R U . . .
C5 C -0.3314(2) -0.3288(4) -0.9816(8) 0.070(2) Uani 1 1 d . . . . .
C6 C -0.3526(2) -0.3570(4) -0.8580(8) 0.0647(19) Uani 1 1 d . . . . .
C7 C -0.3683(2) -0.4318(4) -0.8364(8) 0.080(2) Uani 1 1 d . . . . .
H7 H -0.3671 -0.4729 -0.9000 0.096 Uiso 1 1 calc R U . . .
C8 C -0.3859(2) -0.4337(4) -0.7047(8) 0.081(2) Uani 1 1 d . . . . .
H8 H -0.3995 -0.4754 -0.6632 0.097 Uiso 1 1 calc R U . . .
C9 C -0.3791(2) -0.3602(4) -0.6457(8) 0.0672(19) Uani 1 1 d . . . . .
C10 C -0.3921(2) -0.3242(4) -0.5133(8) 0.071(2) Uani 1 1 d . . . . .
C11 C -0.4126(3) -0.3633(5) -0.4054(9) 0.094(3) Uani 1 1 d . . . . .
H11 H -0.4193 -0.4155 -0.4154 0.113 Uiso 1 1 calc R U . . .
C12 C -0.4228(3) -0.3241(6) -0.2844(9) 0.110(3) Uani 1 1 d . . . . .
H12 H -0.4367 -0.3493 -0.2119 0.132 Uiso 1 1 calc R U . . .
C13 C -0.4122(3) -0.2473(6) -0.2716(8) 0.102(3) Uani 1 1 d . . . . .
H13 H -0.4175 -0.2201 -0.1887 0.122 Uiso 1 1 calc R U . . .
C14 C -0.3939(3) -0.2121(4) -0.3832(9) 0.084(2) Uani 1 1 d . . . . .
H14 H -0.3879 -0.1596 -0.3754 0.101 Uiso 1 1 calc R U . . .
C15 C -0.4501(3) -0.2364(5) -0.8989(8) 0.086(2) Uani 1 1 d . . . . .
H15 H -0.4417 -0.2880 -0.9011 0.103 Uiso 1 1 calc R U . . .
C16 C -0.4879(3) -0.2155(6) -0.9677(9) 0.100(3) Uani 1 1 d . U . . .
H16 H -0.5057 -0.2531 -1.0131 0.120 Uiso 1 1 d R U . . .
C17 C -0.4993(3) -0.1387(6) -0.9674(9) 0.102(3) Uani 1 1 d . U . . .
H17 H -0.5246 -0.1227 -1.0155 0.122 Uiso 1 1 calc R U . . .
C18 C -0.4740(3) -0.0863(5) -0.8972(8) 0.090(2) Uani 1 1 d . . . . .
H18 H -0.4817 -0.0343 -0.8967 0.109 Uiso 1 1 calc R U . . .
C19 C -0.4361(3) -0.1108(5) -0.8253(7) 0.0656(19) Uani 1 1 d . . . . .
C20 C -0.4083(3) -0.0617(5) -0.7401(7) 0.0653(19) Uani 1 1 d . . . . .
C21 C -0.4112(3) 0.0152(5) -0.6991(9) 0.088(2) Uani 1 1 d . . . . .
H21 H -0.4327 0.0498 -0.7287 0.106 Uiso 1 1 calc R U . . .
C22 C -0.3769(3) 0.0311(4) -0.6074(9) 0.083(2) Uani 1 1 d . . . . .
H22 H -0.3708 0.0777 -0.5615 0.099 Uiso 1 1 calc R U . . .
C23 C -0.3527(3) -0.0374(4) -0.5968(7) 0.0616(18) Uani 1 1 d . . . . .
C24 C -0.3144(3) -0.0496(4) -0.5099(7) 0.0585(18) Uani 1 1 d . . . . .
C25 C -0.3006(3) 0.0059(5) -0.4097(9) 0.088(2) Uani 1 1 d . . . . .
H25 H -0.3172 0.0503 -0.4002 0.105 Uiso 1 1 calc R U . . .
C26 C -0.2651(4) -0.0016(6) -0.3277(10) 0.111(3) Uani 1 1 d . . . . .
H26 H -0.2576 0.0367 -0.2617 0.133 Uiso 1 1 calc R U . . .
C27 C -0.2397(3) -0.0653(7) -0.3395(9) 0.109(3) Uani 1 1 d . . . . .
H27 H -0.2140 -0.0703 -0.2861 0.131 Uiso 1 1 calc R U . . .
C28 C -0.2535(3) -0.1218(4) -0.4334(9) 0.080(2) Uani 1 1 d . . . . .
H28 H -0.2376 -0.1672 -0.4387 0.096 Uiso 1 1 calc R U . . .
Cl31 Cl -0.4938(3) -0.4573(6) -0.9087(10) 0.317(5) Uani 0.5 1 d D U P . .
C1 C -0.5000 -0.4912(11) -0.7500 0.086(6) Uani 0.5 2 d DS TU P . .
H1A H -0.4754 -0.5254 -0.7360 0.103 Uiso 0.5 1 calc R U P . .
H1B H -0.5246 -0.5254 -0.7640 0.103 Uiso 0.5 1 calc R U P . .


_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 N5 1.955(5) . ?
Zn1 N2 1.985(5) . ?
Zn1 O2 2.116(5) . ?
Zn1 O1 2.122(5) . ?
Zn1 N3 2.248(5) . ?
Zn1 N4 2.376(6) . ?
O1 N1 1.295(6) . ?
O2 N6 1.303(6) . ?
N1 C29 1.347(8) . ?
N1 C5 1.369(8) . ?
N2 C6 1.351(7) . ?
N2 C9 1.352(7) . ?
N3 C14 1.335(8) . ?
N3 C10 1.345(8) . ?
N4 C15 1.334(8) . ?
N4 C19 1.350(7) . ?
N5 C20 1.355(8) . ?
N5 C23 1.357(7) . ?
N6 C28 1.340(8) . ?
N6 C24 1.365(8) . ?
C29 C2 1.354(10) . ?
C29 H29 0.9300 . ?
C2 C30 1.385(12) . ?
C2 H2 0.9300 . ?
C30 C4 1.343(11) . ?
C30 H30 0.9300 . ?
C4 C5 1.367(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.442(9) . ?
C6 C7 1.401(9) . ?
C7 C8 1.372(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.399(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.461(9) . ?
C10 C11 1.393(9) . ?
C11 C12 1.371(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.358(9) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.365(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(10) . ?
C16 H16 0.9440 . ?
C17 C18 1.354(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.399(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.431(9) . ?
C20 C21 1.387(9) . ?
C21 C22 1.370(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.403(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.431(9) . ?
C24 C25 1.399(9) . ?
C25 C26 1.325(10) . ?
C25 H25 0.9300 . ?
C26 C27 1.362(11) . ?
C26 H26 0.9300 . ?
C27 C28 1.372(10) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
Cl31 C1 1.620(8) . ?
Cl31 Cl31 2.28(2) 5_443 ?
C1 Cl31 1.620(8) 2_453 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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
N5 Zn1 N2 163.9(2) . . ?
N5 Zn1 O2 85.7(2) . . ?
N2 Zn1 O2 109.66(19) . . ?
N5 Zn1 O1 103.30(19) . . ?
N2 Zn1 O1 83.1(2) . . ?
O2 Zn1 O1 87.2(2) . . ?
N5 Zn1 N3 97.5(2) . . ?
N2 Zn1 N3 77.0(2) . . ?
O2 Zn1 N3 93.7(2) . . ?
O1 Zn1 N3 159.2(2) . . ?
N5 Zn1 N4 74.7(2) . . ?
N2 Zn1 N4 90.6(2) . . ?
O2 Zn1 N4 159.2(2) . . ?
O1 Zn1 N4 90.6(2) . . ?
N3 Zn1 N4 95.58(18) . . ?
N1 O1 Zn1 132.7(4) . . ?
N6 O2 Zn1 127.0(4) . . ?
O1 N1 C29 114.8(7) . . ?
O1 N1 C5 123.5(6) . . ?
C29 N1 C5 121.7(7) . . ?
C6 N2 C9 108.2(6) . . ?
C6 N2 Zn1 131.3(5) . . ?
C9 N2 Zn1 118.5(5) . . ?
C14 N3 C10 117.5(6) . . ?
C14 N3 Zn1 130.8(5) . . ?
C10 N3 Zn1 111.6(5) . . ?
C15 N4 C19 119.1(7) . . ?
C15 N4 Zn1 131.6(5) . . ?
C19 N4 Zn1 109.3(5) . . ?
C20 N5 C23 107.4(6) . . ?
C20 N5 Zn1 122.2(5) . . ?
C23 N5 Zn1 130.4(5) . . ?
O2 N6 C28 114.7(7) . . ?
O2 N6 C24 124.4(6) . . ?
C28 N6 C24 120.9(6) . . ?
N1 C29 C2 121.7(8) . . ?
N1 C29 H29 119.1 . . ?
C2 C29 H29 119.1 . . ?
C29 C2 C30 117.7(9) . . ?
C29 C2 H2 121.2 . . ?
C30 C2 H2 121.2 . . ?
C4 C30 C2 119.4(9) . . ?
C4 C30 H30 120.3 . . ?
C2 C30 H30 120.3 . . ?
C30 C4 C5 123.5(8) . . ?
C30 C4 H4 118.2 . . ?
C5 C4 H4 118.2 . . ?
C4 C5 N1 115.8(7) . . ?
C4 C5 C6 121.3(8) . . ?
N1 C5 C6 122.8(6) . . ?
N2 C6 C7 108.3(6) . . ?
N2 C6 C5 124.6(7) . . ?
C7 C6 C5 127.1(7) . . ?
C8 C7 C6 107.9(6) . . ?
C8 C7 H7 126.1 . . ?
C6 C7 H7 126.1 . . ?
C7 C8 C9 106.1(6) . . ?
C7 C8 H8 127.0 . . ?
C9 C8 H8 127.0 . . ?
N2 C9 C8 109.5(6) . . ?
N2 C9 C10 117.4(7) . . ?
C8 C9 C10 133.0(8) . . ?
N3 C10 C11 121.1(7) . . ?
N3 C10 C9 114.6(7) . . ?
C11 C10 C9 124.2(8) . . ?
C12 C11 C10 119.4(8) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 119.2(8) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 118.2(8) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
N3 C14 C13 124.4(8) . . ?
N3 C14 H14 117.8 . . ?
C13 C14 H14 117.8 . . ?
N4 C15 C16 123.0(8) . . ?
N4 C15 H15 118.5 . . ?
C16 C15 H15 118.5 . . ?
C15 C16 C17 118.2(8) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 121.2 . . ?
C18 C17 C16 120.1(9) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 119.6(8) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
N4 C19 C18 120.0(7) . . ?
N4 C19 C20 115.4(7) . . ?
C18 C19 C20 124.5(8) . . ?
N5 C20 C21 109.2(7) . . ?
N5 C20 C19 118.1(7) . . ?
C21 C20 C19 132.7(8) . . ?
C22 C21 C20 107.9(7) . . ?
C22 C21 H21 126.1 . . ?
C20 C21 H21 126.1 . . ?
C21 C22 C23 106.1(7) . . ?
C21 C22 H22 127.0 . . ?
C23 C22 H22 127.0 . . ?
N5 C23 C22 109.5(7) . . ?
N5 C23 C24 123.8(7) . . ?
C22 C23 C24 126.6(8) . . ?
N6 C24 C25 115.8(7) . . ?
N6 C24 C23 123.9(6) . . ?
C25 C24 C23 120.3(7) . . ?
C26 C25 C24 123.1(8) . . ?
C26 C25 H25 118.4 . . ?
C24 C25 H25 118.4 . . ?
C25 C26 C27 120.3(9) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C28 117.4(8) . . ?
C26 C27 H27 121.3 . . ?
C28 C27 H27 121.3 . . ?
N6 C28 C27 122.4(8) . . ?
N6 C28 H28 118.8 . . ?
C27 C28 H28 118.8 . . ?
C1 Cl31 Cl31 115.6(8) . 5_443 ?
Cl31 C1 Cl31 137.5(16) . 2_453 ?
Cl31 C1 H1A 102.7 . . ?
Cl31 C1 H1A 102.7 2_453 . ?
Cl31 C1 H1B 102.7 . . ?
Cl31 C1 H1B 102.7 2_453 . ?
H1A C1 H1B 105.0 . . ?

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 N1 C29 174.6(5) . . . . ?
Zn1 O1 N1 C5 -5.6(10) . . . . ?
Zn1 O2 N6 C28 158.8(5) . . . . ?
Zn1 O2 N6 C24 -20.9(9) . . . . ?
O1 N1 C29 C2 -176.3(8) . . . . ?
C5 N1 C29 C2 3.9(12) . . . . ?
N1 C29 C2 C30 -1.0(15) . . . . ?
C29 C2 C30 C4 -2.1(16) . . . . ?
C2 C30 C4 C5 2.6(16) . . . . ?
C30 C4 C5 N1 0.1(13) . . . . ?
C30 C4 C5 C6 175.8(9) . . . . ?
O1 N1 C5 C4 176.8(7) . . . . ?
C29 N1 C5 C4 -3.4(10) . . . . ?
O1 N1 C5 C6 1.2(10) . . . . ?
C29 N1 C5 C6 -179.0(7) . . . . ?
C9 N2 C6 C7 -1.6(8) . . . . ?
Zn1 N2 C6 C7 -165.1(4) . . . . ?
C9 N2 C6 C5 -179.3(6) . . . . ?
Zn1 N2 C6 C5 17.2(10) . . . . ?
C4 C5 C6 N2 177.9(7) . . . . ?
N1 C5 C6 N2 -6.8(11) . . . . ?
C4 C5 C6 C7 0.6(12) . . . . ?
N1 C5 C6 C7 176.0(7) . . . . ?
N2 C6 C7 C8 2.3(8) . . . . ?
C5 C6 C7 C8 179.9(7) . . . . ?
C6 C7 C8 C9 -2.0(8) . . . . ?
C6 N2 C9 C8 0.4(8) . . . . ?
Zn1 N2 C9 C8 166.3(4) . . . . ?
C6 N2 C9 C10 -175.5(6) . . . . ?
Zn1 N2 C9 C10 -9.5(8) . . . . ?
C7 C8 C9 N2 1.0(8) . . . . ?
C7 C8 C9 C10 176.0(7) . . . . ?
C14 N3 C10 C11 3.5(10) . . . . ?
Zn1 N3 C10 C11 -174.2(6) . . . . ?
C14 N3 C10 C9 -178.3(6) . . . . ?
Zn1 N3 C10 C9 4.1(7) . . . . ?
N2 C9 C10 N3 2.8(9) . . . . ?
C8 C9 C10 N3 -171.9(7) . . . . ?
N2 C9 C10 C11 -179.0(6) . . . . ?
C8 C9 C10 C11 6.3(13) . . . . ?
N3 C10 C11 C12 -2.8(12) . . . . ?
C9 C10 C11 C12 179.1(7) . . . . ?
C10 C11 C12 C13 -0.6(13) . . . . ?
C11 C12 C13 C14 3.2(13) . . . . ?
C10 N3 C14 C13 -0.7(11) . . . . ?
Zn1 N3 C14 C13 176.4(5) . . . . ?
C12 C13 C14 N3 -2.7(13) . . . . ?
C19 N4 C15 C16 -0.5(10) . . . . ?
Zn1 N4 C15 C16 -178.1(5) . . . . ?
N4 C15 C16 C17 1.9(12) . . . . ?
C15 C16 C17 C18 -1.6(12) . . . . ?
C16 C17 C18 C19 0.1(12) . . . . ?
C15 N4 C19 C18 -1.1(9) . . . . ?
Zn1 N4 C19 C18 177.0(5) . . . . ?
C15 N4 C19 C20 176.2(6) . . . . ?
Zn1 N4 C19 C20 -5.7(6) . . . . ?
C17 C18 C19 N4 1.3(10) . . . . ?
C17 C18 C19 C20 -175.7(7) . . . . ?
C23 N5 C20 C21 0.6(7) . . . . ?
Zn1 N5 C20 C21 178.7(4) . . . . ?
C23 N5 C20 C19 -176.5(5) . . . . ?
Zn1 N5 C20 C19 1.6(8) . . . . ?
N4 C19 C20 N5 3.6(9) . . . . ?
C18 C19 C20 N5 -179.3(6) . . . . ?
N4 C19 C20 C21 -172.7(7) . . . . ?
C18 C19 C20 C21 4.4(12) . . . . ?
N5 C20 C21 C22 -1.3(8) . . . . ?
C19 C20 C21 C22 175.3(7) . . . . ?
C20 C21 C22 C23 1.4(8) . . . . ?
C20 N5 C23 C22 0.2(7) . . . . ?
Zn1 N5 C23 C22 -177.6(4) . . . . ?
C20 N5 C23 C24 177.6(6) . . . . ?
Zn1 N5 C23 C24 -0.3(9) . . . . ?
C21 C22 C23 N5 -1.0(8) . . . . ?
C21 C22 C23 C24 -178.2(6) . . . . ?
O2 N6 C24 C25 179.7(6) . . . . ?
C28 N6 C24 C25 0.1(9) . . . . ?
O2 N6 C24 C23 -0.4(10) . . . . ?
C28 N6 C24 C23 179.9(6) . . . . ?
N5 C23 C24 N6 12.1(10) . . . . ?
C22 C23 C24 N6 -171.0(6) . . . . ?
N5 C23 C24 C25 -168.0(6) . . . . ?
C22 C23 C24 C25 8.8(10) . . . . ?
N6 C24 C25 C26 0.8(11) . . . . ?
C23 C24 C25 C26 -179.1(7) . . . . ?
C24 C25 C26 C27 0.9(13) . . . . ?
C25 C26 C27 C28 -3.2(13) . . . . ?
O2 N6 C28 C27 177.7(7) . . . . ?
C24 N6 C28 C27 -2.6(10) . . . . ?
C26 C27 C28 N6 4.1(12) . . . . ?
Cl31 Cl31 C1 Cl31 -163.0(8) 5_443 . . 2_453 ?

_refine_diff_density_max         0.805
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.068

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_HL2
_database_code_depnum_ccdc_archive 'CCDC 1976444'
loop_
_audit_author_name
_audit_author_address
'XiuFang Mu'
;zhongnandaxue
China
;
_audit_update_record             
;
2020-06-23 deposited with the CCDC.	2020-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H17 N3 O5'
_chemical_formula_weight         307.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   16.0485(5)
_cell_length_b                   8.2154(2)
_cell_length_c                   22.2672(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2935.82(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2856
_cell_measurement_theta_min      1.85
_cell_measurement_theta_max      28.62

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6444
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
'SADABS-2008/1 - Bruker AXS was used for absorption correction. wR2(int) was 0.0672 before and 0.0527 after correction. The Ratio of minimum to maximum transmission is 0.8148. The  Lambda/2 correction factor is 0.0015.'


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14549
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.226
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2865
_reflns_number_gt                1715
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1126P)²+0.7322P]
 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         2865
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1417
_refine_ls_R_factor_gt           0.0793
_refine_ls_wR_factor_ref         0.2090
_refine_ls_wR_factor_gt          0.1896
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
C10 C 0.2959(2) 0.1763(4) 0.28480(14) 0.0271(8) Uani 1 1 d . . . . .
C12 C 0.2856(2) 0.0194(4) 0.37549(16) 0.0391(9) Uani 1 1 d . . . . .
H12 H 0.2533 -0.0287 0.4053 0.047 Uiso 1 1 calc R U . . .
C9 C 0.2567(2) 0.2662(4) 0.23662(14) 0.0270(8) Uani 1 1 d . . . . .
N1 N 0.34976(17) 0.5367(3) 0.08872(12) 0.0297(7) Uani 1 1 d . . . . .
C6 C 0.2438(2) 0.4211(4) 0.15520(14) 0.0258(8) Uani 1 1 d . . . . .
C5 C 0.2675(2) 0.5219(4) 0.10496(14) 0.0257(8) Uani 1 1 d . . . . .
C2 C 0.3153(2) 0.7181(4) 0.00993(15) 0.0328(9) Uani 1 1 d . . . . .
H2 H 0.3322 0.7862 -0.0211 0.039 Uiso 1 1 calc R U . . .
C8 C 0.1719(2) 0.2848(4) 0.22556(15) 0.0305(8) Uani 1 1 d . . . . .
H8 H 0.1286 0.2404 0.2480 0.037 Uiso 1 1 calc R U . . .
C1 C 0.3725(2) 0.6348(4) 0.04270(15) 0.0344(9) Uani 1 1 d . . . . .
H1 H 0.4287 0.6454 0.0333 0.041 Uiso 1 1 calc R U . . .
C4 C 0.2093(2) 0.6045(4) 0.07050(14) 0.0306(8) Uani 1 1 d . . . . .
H4 H 0.1531 0.5942 0.0799 0.037 Uiso 1 1 calc R U . . .
C7 C 0.1640(2) 0.3818(4) 0.17484(14) 0.0301(8) Uani 1 1 d . . . . .
H7 H 0.1143 0.4147 0.1572 0.036 Uiso 1 1 calc R U . . .
C11 C 0.2488(2) 0.1011(4) 0.32982(14) 0.0309(8) Uani 1 1 d . . . . .
H11 H 0.1910 0.1073 0.3283 0.037 Uiso 1 1 calc R U . . .
C3 C 0.2317(2) 0.7003(4) 0.02333(15) 0.0339(9) Uani 1 1 d . . . . .
H3 H 0.1914 0.7530 0.0005 0.041 Uiso 1 1 calc R U . . .
C14 C 0.4178(2) 0.0803(4) 0.33420(15) 0.0350(9) Uani 1 1 d . . . . .
H14 H 0.4755 0.0728 0.3356 0.042 Uiso 1 1 calc R U . . .
C13 C 0.3714(2) 0.0082(5) 0.37752(16) 0.0406(10) Uani 1 1 d . . . . .
H13 H 0.3973 -0.0487 0.4085 0.049 Uiso 1 1 calc R U . . .
N3 N 0.29854(16) 0.3492(3) 0.19324(11) 0.0254(7) Uani 1 1 d . . . . .
H3A H 0.3519 0.3553 0.1904 0.030 Uiso 1 1 calc R U . . .
O1 O 0.40923(15) 0.4551(3) 0.11698(11) 0.0395(7) Uani 1 1 d . . . . .
O2 O 0.43012(14) 0.2339(3) 0.24803(10) 0.0344(6) Uani 1 1 d . . . . .
N2 N 0.38071(17) 0.1637(3) 0.28878(12) 0.0299(7) Uani 1 1 d . . . . .
O3 O 0.03756(17) 0.0186(3) 0.30994(12) 0.0443(7) Uani 1 1 d G . . . .
H3B H 0.0420 -0.0564 0.2839 0.066 Uiso 1 1 d G U . . .
H3C H 0.0043 0.0870 0.2942 0.066 Uiso 1 1 d G U . . .
O4 O 0.5274(2) 0.7562(4) -0.02636(14) 0.0623(9) Uani 1 1 d G . . . .
H4A H 0.5410 0.6661 -0.0423 0.093 Uiso 1 1 d G U . . .
H4B H 0.5023 0.8077 -0.0541 0.093 Uiso 1 1 d G U . . .
O5 O 0.4250(2) 1.0071(4) -0.06903(14) 0.0694(9) Uani 1 1 d G . . . .
H5A H 0.4511 1.0911 -0.0570 0.104 Uiso 1 1 d G U . . .
H5B H 0.4396 0.9964 -0.1055 0.104 Uiso 1 1 d G 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
C10 N2 1.369(4) . ?
C10 C11 1.399(5) . ?
C10 C9 1.446(5) . ?
C12 C11 1.354(5) . ?
C12 C13 1.381(5) . ?
C12 H12 0.9300 . ?
C9 N3 1.359(4) . ?
C9 C8 1.392(5) . ?
N1 O1 1.325(3) . ?
N1 C1 1.354(4) . ?
N1 C5 1.374(4) . ?
C6 N3 1.356(4) . ?
C6 C7 1.391(5) . ?
C6 C5 1.443(5) . ?
C5 C4 1.386(4) . ?
C2 C1 1.357(5) . ?
C2 C3 1.383(5) . ?
C2 H2 0.9300 . ?
C8 C7 1.388(5) . ?
C8 H8 0.9300 . ?
C1 H1 0.9300 . ?
C4 C3 1.361(5) . ?
C4 H4 0.9300 . ?
C7 H7 0.9300 . ?
C11 H11 0.9300 . ?
C3 H3 0.9300 . ?
C14 C13 1.355(5) . ?
C14 N2 1.358(4) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
N3 H3A 0.8600 . ?
O2 N2 1.336(3) . ?
O3 H3B 0.8499 . ?
O3 H3C 0.8500 . ?
O4 H4A 0.8498 . ?
O4 H4B 0.8497 . ?
O5 H5A 0.8501 . ?
O5 H5B 0.8500 . ?

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
N2 C10 C11 117.2(3) . . ?
N2 C10 C9 121.3(3) . . ?
C11 C10 C9 121.5(3) . . ?
C11 C12 C13 119.5(3) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
N3 C9 C8 107.6(3) . . ?
N3 C9 C10 124.7(3) . . ?
C8 C9 C10 127.7(3) . . ?
O1 N1 C1 117.8(3) . . ?
O1 N1 C5 121.5(3) . . ?
C1 N1 C5 120.7(3) . . ?
N3 C6 C7 107.4(3) . . ?
N3 C6 C5 124.3(3) . . ?
C7 C6 C5 128.3(3) . . ?
N1 C5 C4 117.2(3) . . ?
N1 C5 C6 120.5(3) . . ?
C4 C5 C6 122.2(3) . . ?
C1 C2 C3 119.1(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C7 C8 C9 107.2(3) . . ?
C7 C8 H8 126.4 . . ?
C9 C8 H8 126.4 . . ?
N1 C1 C2 121.7(3) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C4 C5 122.2(3) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C8 C7 C6 107.7(3) . . ?
C8 C7 H7 126.1 . . ?
C6 C7 H7 126.1 . . ?
C12 C11 C10 121.5(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C13 C14 N2 120.7(3) . . ?
C13 C14 H14 119.7 . . ?
N2 C14 H14 119.7 . . ?
C14 C13 C12 119.7(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C6 N3 C9 110.0(3) . . ?
C6 N3 H3A 125.0 . . ?
C9 N3 H3A 125.0 . . ?
O2 N2 C14 117.6(3) . . ?
O2 N2 C10 120.9(3) . . ?
C14 N2 C10 121.5(3) . . ?
H3B O3 H3C 104.5 . . ?
H4A O4 H4B 104.5 . . ?
H5A O5 H5B 104.5 . . ?

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
N2 C10 C9 N3 -2.4(5) . . . . ?
C11 C10 C9 N3 176.4(3) . . . . ?
N2 C10 C9 C8 177.5(3) . . . . ?
C11 C10 C9 C8 -3.6(5) . . . . ?
O1 N1 C5 C4 -176.3(3) . . . . ?
C1 N1 C5 C4 3.1(4) . . . . ?
O1 N1 C5 C6 2.5(4) . . . . ?
C1 N1 C5 C6 -178.1(3) . . . . ?
N3 C6 C5 N1 7.2(5) . . . . ?
C7 C6 C5 N1 -174.4(3) . . . . ?
N3 C6 C5 C4 -174.1(3) . . . . ?
C7 C6 C5 C4 4.3(5) . . . . ?
N3 C9 C8 C7 -0.5(4) . . . . ?
C10 C9 C8 C7 179.6(3) . . . . ?
O1 N1 C1 C2 177.6(3) . . . . ?
C5 N1 C1 C2 -1.9(5) . . . . ?
C3 C2 C1 N1 -1.0(5) . . . . ?
N1 C5 C4 C3 -1.7(5) . . . . ?
C6 C5 C4 C3 179.6(3) . . . . ?
C9 C8 C7 C6 0.3(4) . . . . ?
N3 C6 C7 C8 0.0(3) . . . . ?
C5 C6 C7 C8 -178.6(3) . . . . ?
C13 C12 C11 C10 -0.8(5) . . . . ?
N2 C10 C11 C12 0.1(5) . . . . ?
C9 C10 C11 C12 -178.8(3) . . . . ?
C5 C4 C3 C2 -1.1(5) . . . . ?
C1 C2 C3 C4 2.5(5) . . . . ?
N2 C14 C13 C12 0.0(5) . . . . ?
C11 C12 C13 C14 0.7(6) . . . . ?
C7 C6 N3 C9 -0.3(3) . . . . ?
C5 C6 N3 C9 178.4(3) . . . . ?
C8 C9 N3 C6 0.5(4) . . . . ?
C10 C9 N3 C6 -179.5(3) . . . . ?
C13 C14 N2 O2 179.1(3) . . . . ?
C13 C14 N2 C10 -0.7(5) . . . . ?
C11 C10 N2 O2 -179.1(3) . . . . ?
C9 C10 N2 O2 -0.2(4) . . . . ?
C11 C10 N2 C14 0.6(4) . . . . ?
C9 C10 N2 C14 179.5(3) . . . . ?

_refine_diff_density_max         0.766
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.070

_shelxl_version_number           2013-2

