# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_bwn18272
_database_code_depnum_ccdc_archive 'CCDC 1881671'
loop_
_audit_author_name
_audit_author_address
'Xiaoming Yang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2018-11-27 deposited with the CCDC.	2019-08-06 downloaded from the CCDC.
;
_audit_creation_date             2018-09-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H16 Mn N4 O6, 2(C6 H2 N3 O7)'
_chemical_formula_sum            'C16 H20 Mn N10 O20'
_chemical_formula_weight         727.36
_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'
Mn Mn 0.3368 0.7283 '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           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                   14.417(3)
_cell_length_b                   7.9325(16)
_cell_length_c                   24.414(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.44(3)
_cell_angle_gamma                90
_cell_volume                     2736.5(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5227
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      31.3634
_cell_measurement_theta_min      1.7021
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.885
_exptl_absorpt_coefficient_mu    0.594
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1484
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            18765
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.364
_diffrn_reflns_theta_min         3.044
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega 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                3862
_reflns_number_total             4165
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.943
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.084
_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     214
_refine_ls_number_reflns         4165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0541
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²+5.0513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1323
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O8(H8A,H8B)
2.b Secondary CH2 refined with riding coordinates:
 N4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C6(H6)
2.d Idealised Me refined as rotating group:
 C8(H8C,H8D,H8E)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.500000 0.29217(5) 0.750000 0.02041(12) Uani 1 2 d S T P . .
O9 O 0.44050(10) 0.47280(19) 0.80104(6) 0.0251(3) Uani 1 1 d . . . . .
O5 O 0.67689(10) 0.1693(2) 0.64464(6) 0.0243(3) Uani 1 1 d . . . . .
O3 O 0.85493(12) 0.5231(2) 0.64767(7) 0.0374(4) Uani 1 1 d . . . . .
O8 O 0.54851(11) 0.0889(2) 0.70549(6) 0.0283(3) Uani 1 1 d . . . . .
H8A H 0.584561 0.109825 0.683222 0.034 Uiso 1 1 d R . . . .
H8B H 0.503990 0.025605 0.690442 0.034 Uiso 1 1 d R . . . .
O7 O 0.43966(11) 0.1571(2) 0.51619(7) 0.0312(3) Uani 1 1 d . . . . .
O1 O 0.58569(12) 0.5389(2) 0.41361(6) 0.0341(4) Uani 1 1 d . . . . .
O6 O 0.51694(12) 0.0217(2) 0.58734(7) 0.0347(4) Uani 1 1 d . . . . .
N2 N 0.82847(12) 0.3792(2) 0.63396(7) 0.0246(3) Uani 1 1 d . . . . .
O4 O 0.86956(12) 0.2531(3) 0.65468(9) 0.0433(5) Uani 1 1 d . . . . .
O2 O 0.73134(12) 0.6175(2) 0.44265(7) 0.0359(4) Uani 1 1 d . . . . .
O10 O 0.32439(11) 0.6600(2) 0.80309(7) 0.0330(4) Uani 1 1 d . . . . .
N5 N 0.51147(12) 0.1338(2) 0.55219(7) 0.0222(3) Uani 1 1 d . . . . .
N4 N 0.35689(12) 0.3729(2) 0.69864(7) 0.0234(3) Uani 1 1 d . . . . .
H4A H 0.364865 0.417846 0.665592 0.028 Uiso 1 1 calc R . . . .
H4B H 0.318293 0.281527 0.691092 0.028 Uiso 1 1 calc R . . . .
N1 N 0.66025(13) 0.5394(2) 0.44876(7) 0.0258(4) Uani 1 1 d . . . . .
N3 N 0.31489(12) 0.4938(2) 0.72877(7) 0.0265(4) Uani 1 1 d . . . . .
H3 H 0.258869 0.537405 0.715321 0.032 Uiso 1 1 calc R . . . .
C3 C 0.59315(13) 0.2419(2) 0.55176(8) 0.0197(3) Uani 1 1 d . . . . .
C2 C 0.58961(14) 0.3374(3) 0.50408(8) 0.0220(4) Uani 1 1 d . . . . .
H2 H 0.536001 0.330576 0.474415 0.026 Uiso 1 1 calc R . . . .
C6 C 0.74307(14) 0.4572(3) 0.54258(8) 0.0218(4) Uani 1 1 d . . . . .
H6 H 0.793519 0.531585 0.539701 0.026 Uiso 1 1 calc R . . . .
C5 C 0.74531(13) 0.3598(3) 0.58939(8) 0.0206(3) Uani 1 1 d . . . . .
C4 C 0.67174(13) 0.2457(3) 0.59926(7) 0.0197(3) Uani 1 1 d . . . . .
C7 C 0.36513(13) 0.5382(3) 0.77886(8) 0.0220(4) Uani 1 1 d . . . . .
C1 C 0.66405(14) 0.4428(3) 0.49950(8) 0.0222(4) Uani 1 1 d . . . . .
C8 C 0.37721(17) 0.7163(3) 0.85695(10) 0.0324(5) Uani 1 1 d . . . . .
H8C H 0.442094 0.744340 0.853687 0.049 Uiso 1 1 calc GR . . . .
H8D H 0.378484 0.626265 0.884572 0.049 Uiso 1 1 calc GR . . . .
H8E H 0.346659 0.816376 0.868929 0.049 Uiso 1 1 calc GR . . . .


_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
Mn1 O9 2.1830(15) . ?
Mn1 O9 2.1830(15) 2_656 ?
Mn1 O8 2.1382(16) . ?
Mn1 O8 2.1382(16) 2_656 ?
Mn1 N4 2.2832(18) 2_656 ?
Mn1 N4 2.2831(18) . ?
O9 C7 1.229(2) . ?
O5 C4 1.252(2) . ?
O3 N2 1.228(3) . ?
O8 H8A 0.8399 . ?
O8 H8B 0.8398 . ?
O7 N5 1.232(2) . ?
O1 N1 1.235(2) . ?
O6 N5 1.227(2) . ?
N2 O4 1.220(3) . ?
N2 C5 1.458(2) . ?
O2 N1 1.232(2) . ?
O10 C7 1.329(2) . ?
O10 C8 1.453(3) . ?
N5 C3 1.459(2) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N4 N3 1.416(2) . ?
N1 C1 1.449(2) . ?
N3 H3 0.8800 . ?
N3 C7 1.339(3) . ?
C3 C2 1.381(3) . ?
C3 C4 1.452(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.382(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.374(3) . ?
C6 C1 1.393(3) . ?
C5 C4 1.450(3) . ?
C8 H8C 0.9800 . ?
C8 H8D 0.9800 . ?
C8 H8E 0.9800 . ?

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
O9 Mn1 O9 97.95(9) . 2_656 ?
O9 Mn1 N4 73.43(6) 2_656 2_656 ?
O9 Mn1 N4 85.24(6) 2_656 . ?
O9 Mn1 N4 85.24(6) . 2_656 ?
O9 Mn1 N4 73.43(6) . . ?
O8 Mn1 O9 89.99(6) 2_656 . ?
O8 Mn1 O9 89.99(6) . 2_656 ?
O8 Mn1 O9 172.00(6) . . ?
O8 Mn1 O9 172.00(6) 2_656 2_656 ?
O8 Mn1 O8 82.09(9) . 2_656 ?
O8 Mn1 N4 106.47(6) . . ?
O8 Mn1 N4 98.02(6) 2_656 . ?
O8 Mn1 N4 98.02(6) . 2_656 ?
O8 Mn1 N4 106.46(6) 2_656 2_656 ?
N4 Mn1 N4 147.43(9) . 2_656 ?
C7 O9 Mn1 116.03(13) . . ?
Mn1 O8 H8A 119.1 . . ?
Mn1 O8 H8B 112.0 . . ?
H8A O8 H8B 110.6 . . ?
O3 N2 C5 117.78(18) . . ?
O4 N2 O3 123.34(19) . . ?
O4 N2 C5 118.85(18) . . ?
C7 O10 C8 115.33(16) . . ?
O7 N5 C3 118.15(17) . . ?
O6 N5 O7 122.42(18) . . ?
O6 N5 C3 119.42(16) . . ?
Mn1 N4 H4A 109.7 . . ?
Mn1 N4 H4B 109.7 . . ?
H4A N4 H4B 108.2 . . ?
N3 N4 Mn1 109.73(11) . . ?
N3 N4 H4A 109.7 . . ?
N3 N4 H4B 109.7 . . ?
O1 N1 C1 118.19(17) . . ?
O2 N1 O1 123.22(18) . . ?
O2 N1 C1 118.59(17) . . ?
N4 N3 H3 121.9 . . ?
C7 N3 N4 116.30(16) . . ?
C7 N3 H3 121.9 . . ?
C2 C3 N5 115.69(17) . . ?
C2 C3 C4 123.67(18) . . ?
C4 C3 N5 120.64(16) . . ?
C3 C2 H2 120.0 . . ?
C3 C2 C1 120.00(18) . . ?
C1 C2 H2 120.0 . . ?
C5 C6 H6 121.2 . . ?
C5 C6 C1 117.53(18) . . ?
C1 C6 H6 121.2 . . ?
C6 C5 N2 116.19(17) . . ?
C6 C5 C4 126.25(17) . . ?
C4 C5 N2 117.51(17) . . ?
O5 C4 C3 126.62(18) . . ?
O5 C4 C5 122.15(17) . . ?
C5 C4 C3 111.16(16) . . ?
O9 C7 O10 122.76(18) . . ?
O9 C7 N3 124.23(19) . . ?
O10 C7 N3 113.00(17) . . ?
C2 C1 N1 119.40(17) . . ?
C2 C1 C6 121.36(18) . . ?
C6 C1 N1 119.24(18) . . ?
O10 C8 H8C 109.5 . . ?
O10 C8 H8D 109.5 . . ?
O10 C8 H8E 109.5 . . ?
H8C C8 H8D 109.5 . . ?
H8C C8 H8E 109.5 . . ?
H8D C8 H8E 109.5 . . ?

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
Mn1 O9 C7 O10 -174.48(15) . . . . ?
Mn1 O9 C7 N3 6.5(3) . . . . ?
Mn1 N4 N3 C7 1.0(2) . . . . ?
O3 N2 C5 C6 46.5(3) . . . . ?
O3 N2 C5 C4 -131.2(2) . . . . ?
O7 N5 C3 C2 -13.2(3) . . . . ?
O7 N5 C3 C4 166.78(18) . . . . ?
O1 N1 C1 C2 8.0(3) . . . . ?
O1 N1 C1 C6 -172.40(19) . . . . ?
O6 N5 C3 C2 165.53(18) . . . . ?
O6 N5 C3 C4 -14.5(3) . . . . ?
N2 C5 C4 O5 2.0(3) . . . . ?
N2 C5 C4 C3 179.00(16) . . . . ?
O4 N2 C5 C6 -131.6(2) . . . . ?
O4 N2 C5 C4 50.7(3) . . . . ?
O2 N1 C1 C2 -171.78(19) . . . . ?
O2 N1 C1 C6 7.8(3) . . . . ?
N5 C3 C2 C1 -179.44(17) . . . . ?
N5 C3 C4 O5 -4.0(3) . . . . ?
N5 C3 C4 C5 179.20(17) . . . . ?
N4 N3 C7 O9 -5.2(3) . . . . ?
N4 N3 C7 O10 175.77(17) . . . . ?
C3 C2 C1 N1 178.69(18) . . . . ?
C3 C2 C1 C6 -0.9(3) . . . . ?
C2 C3 C4 O5 176.0(2) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C6 C5 C4 O5 -175.47(19) . . . . ?
C6 C5 C4 C3 1.5(3) . . . . ?
C5 C6 C1 N1 -178.13(18) . . . . ?
C5 C6 C1 C2 1.4(3) . . . . ?
C4 C3 C2 C1 0.6(3) . . . . ?
C1 C6 C5 N2 -179.36(17) . . . . ?
C1 C6 C5 C4 -1.9(3) . . . . ?
C8 O10 C7 O9 2.5(3) . . . . ?
C8 O10 C7 N3 -178.39(19) . . . . ?

_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_bwn18252a
_database_code_depnum_ccdc_archive 'CCDC 1882305'
loop_
_audit_author_name
_audit_author_address
'Xiaoming Yang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2018-11-30 deposited with the CCDC.	2019-08-06 downloaded from the CCDC.
;
_audit_creation_date             2018-09-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H16 Cu N4 O6, 2(C6 H2 N3 O7)'
_chemical_formula_sum            'C16 H20 Cu N10 O20'
_chemical_formula_weight         735.96
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.1087(14)
_cell_length_b                   14.163(3)
_cell_length_c                   15.289(3)
_cell_angle_alpha                112.32(3)
_cell_angle_beta                 100.42(3)
_cell_angle_gamma                103.26(3)
_cell_volume                     1323.2(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4110
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      1.5082
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.941
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             750
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0802
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9808
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         1.672
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega 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                4865
_reflns_number_total             5940
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.879
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         5940
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0842
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0313P)²+5.2194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1541
_refine_ls_wR_factor_ref         0.1677
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O10(H10A,H10B), O11(H11A,H11B)
2.b Secondary CH2 refined with riding coordinates:
 N5(H5A,H5B), N6(H6A,H6B)
2.c Me refined with riding coordinates:
 C10(H10C,H10D,H10E)
2.d Aromatic/amide H refined with riding coordinates:
 N4(H4), N7(H7), C2(H2), C6(H6), C12(H12), C14(H14)
2.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu01 Cu 0.27483(9) 0.49715(5) 0.27028(4) 0.01991(17) Uani 1 1 d . . . . .
O1 O 0.0010(6) 1.1804(3) 0.2925(3) 0.0341(9) Uani 1 1 d . . . . .
O2 O 0.0395(7) 1.1210(3) 0.1462(3) 0.0387(10) Uani 1 1 d . . . . .
O3 O 0.0681(7) 0.7653(3) -0.0107(3) 0.0392(11) Uani 1 1 d . . . . .
O4 O -0.0597(6) 0.6431(3) 0.0336(3) 0.0305(9) Uani 1 1 d . . . . .
O5 O -0.0194(5) 0.7154(3) 0.2279(2) 0.0231(8) Uani 1 1 d . . . . .
O6 O -0.0873(6) 0.8185(3) 0.4072(3) 0.0307(9) Uani 1 1 d . . . . .
O7 O 0.1668(6) 0.9678(3) 0.4753(3) 0.0313(9) Uani 1 1 d . . . . .
O8 O 0.6685(5) 0.4803(3) 0.1149(3) 0.0276(8) Uani 1 1 d . . . . .
O9 O 0.4045(5) 0.4296(3) 0.1687(2) 0.0208(7) Uani 1 1 d . . . . .
O10 O 0.1436(5) 0.5524(3) 0.1568(2) 0.0257(8) Uani 1 1 d . . . . .
H10A H 0.090184 0.521290 0.095075 0.031 Uiso 1 1 d R . . . .
H10B H 0.106884 0.607250 0.169265 0.031 Uiso 1 1 d R . . . .
O11 O 0.4235(6) 0.4437(3) 0.3892(3) 0.0309(9) Uani 1 1 d . . . . .
H11A H 0.454617 0.387276 0.366887 0.037 Uiso 1 1 d R . . . .
H11B H 0.307807 0.430416 0.396867 0.037 Uiso 1 1 d R . . . .
O12 O 0.1469(5) 0.5685(3) 0.3699(2) 0.0207(7) Uani 1 1 d . . . . .
O13 O -0.1278(5) 0.5329(3) 0.4202(2) 0.0229(8) Uani 1 1 d . . . . .
O14 O 0.4299(6) 0.2782(3) 0.4632(3) 0.0299(9) Uani 1 1 d . . . A 1
O15 O 0.5904(6) 0.1993(3) 0.5307(3) 0.0323(9) Uani 1 1 d . . . A 1
O16 O 0.4910(7) -0.1681(3) 0.3074(3) 0.0382(10) Uani 1 1 d . . . B 2
O17 O 0.5129(7) -0.2050(3) 0.1597(3) 0.0382(10) Uani 1 1 d . . . B 2
O18 O 0.3569(6) 0.0548(3) 0.0304(3) 0.0313(9) Uani 1 1 d . . . . .
O19 O 0.6132(6) 0.2018(3) 0.1165(3) 0.0351(10) Uani 1 1 d . . . . .
O20 O 0.5577(5) 0.2763(3) 0.3023(3) 0.0243(8) Uani 1 1 d . . . . .
N1 N 0.0167(7) 1.1084(3) 0.2196(3) 0.0257(9) Uani 1 1 d . . . . .
N2 N 0.0005(6) 0.7386(3) 0.0482(3) 0.0219(9) Uani 1 1 d . . . . .
N3 N 0.0310(6) 0.8941(3) 0.4035(3) 0.0207(9) Uani 1 1 d . . . . .
N4 N 0.6440(6) 0.5959(3) 0.2551(3) 0.0226(9) Uani 1 1 d . . . . .
H4 H 0.765188 0.639137 0.265882 0.027 Uiso 1 1 calc R . . . .
N5 N 0.5228(6) 0.6259(3) 0.3177(3) 0.0193(8) Uani 1 1 d . . . . .
H5A H 0.487856 0.682763 0.314751 0.023 Uiso 1 1 calc R . . . .
H5B H 0.591728 0.645485 0.381562 0.023 Uiso 1 1 calc R . . . .
N6 N 0.0201(6) 0.3708(3) 0.2248(3) 0.0200(8) Uani 1 1 d . . . . .
H6A H -0.045943 0.348568 0.159980 0.024 Uiso 1 1 calc R . . . .
H6B H 0.050847 0.314495 0.231521 0.024 Uiso 1 1 calc R . . . .
N7 N -0.1029(6) 0.4068(3) 0.2852(3) 0.0226(9) Uani 1 1 d . . . . .
H7 H -0.226675 0.366493 0.274656 0.027 Uiso 1 1 calc R . . . .
N8 N 0.5158(6) 0.2112(3) 0.4581(3) 0.0206(9) Uani 1 1 d . . . A 1
N9 N 0.5023(6) -0.1440(3) 0.2390(3) 0.0227(9) Uani 1 1 d . . . B 2
N10 N 0.4910(7) 0.1190(3) 0.1074(3) 0.0229(9) Uani 1 1 d . . . . .
C1 C 0.0084(7) 1.0065(4) 0.2207(4) 0.0222(10) Uani 1 1 d . . . . .
C2 C 0.0049(7) 0.9213(4) 0.1362(4) 0.0218(10) Uani 1 1 d . . . . .
H2 H 0.009295 0.930122 0.077917 0.026 Uiso 1 1 calc R . . . .
C3 C -0.0053(7) 0.8229(4) 0.1376(3) 0.0184(10) Uani 1 1 d . . . . .
C4 C -0.0104(7) 0.8032(4) 0.2237(3) 0.0180(9) Uani 1 1 d . . . . .
C5 C 0.0095(7) 0.9002(4) 0.3087(3) 0.0197(10) Uani 1 1 d . . . . .
C6 C 0.0173(7) 0.9967(4) 0.3092(4) 0.0213(10) Uani 1 1 d . . . . .
H6 H 0.028592 1.056577 0.368303 0.026 Uiso 1 1 calc R . . . .
C7 C 0.5795(8) 0.3825(4) 0.0229(4) 0.0284(12) Uani 1 1 d . . . . .
H7A H 0.448684 0.381732 -0.011969 0.043 Uiso 1 1 calc GR . . . .
H7B H 0.559367 0.319571 0.037037 0.043 Uiso 1 1 calc GR . . . .
H7C H 0.670031 0.379952 -0.018626 0.043 Uiso 1 1 calc GR . . . .
C8 C 0.5631(7) 0.4979(4) 0.1786(3) 0.0200(10) Uani 1 1 d . . . . .
C9 C -0.0176(7) 0.5059(4) 0.3587(3) 0.0194(10) Uani 1 1 d . . . . .
C10 C -0.0353(8) 0.6401(4) 0.5032(4) 0.0237(11) Uani 1 1 d . . . . .
H10C H -0.125935 0.653335 0.544415 0.036 Uiso 1 1 calc R . . . .
H10D H 0.094003 0.644531 0.542875 0.036 Uiso 1 1 calc R . . . .
H10E H -0.011885 0.694545 0.477979 0.036 Uiso 1 1 calc R . . . .
C11 C 0.5215(7) 0.1404(4) 0.3610(3) 0.0177(9) Uani 1 1 d . . . . .
C12 C 0.5171(7) 0.0381(4) 0.3468(3) 0.0179(9) Uani 1 1 d . . . . .
H12 H 0.521301 0.018551 0.399870 0.021 Uiso 1 1 calc R . . . .
C13 C 0.5063(7) -0.0361(4) 0.2541(3) 0.0181(9) Uani 1 1 d . . . . .
C14 C 0.4956(7) -0.0096(4) 0.1748(3) 0.0196(10) Uani 1 1 d . . . . .
H14 H 0.479747 -0.062283 0.110336 0.024 Uiso 1 1 calc R . . . .
C15 C 0.5086(7) 0.0941(4) 0.1920(3) 0.0181(9) Uani 1 1 d . . . . .
C16 C 0.5312(7) 0.1793(4) 0.2869(3) 0.0175(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu01 O9 1.993(3) . ?
Cu01 O10 2.297(3) . ?
Cu01 O11 2.390(4) . ?
Cu01 O12 1.980(3) . ?
Cu01 N5 2.004(4) . ?
Cu01 N6 2.019(4) . ?
O1 N1 1.235(6) . ?
O2 N1 1.234(6) . ?
O3 N2 1.231(5) . ?
O4 N2 1.238(5) . ?
O5 C4 1.257(6) . ?
O6 N3 1.228(5) . ?
O7 N3 1.228(5) . ?
O8 C7 1.447(6) . ?
O8 C8 1.318(5) . ?
O9 C8 1.248(6) . ?
O10 H10A 0.8403 . ?
O10 H10B 0.8400 . ?
O11 H11A 0.8398 . ?
O11 H11B 0.8400 . ?
O12 C9 1.233(6) . ?
O13 C9 1.332(5) . ?
O13 C10 1.458(6) . ?
O14 N8 1.227(5) . ?
O15 N8 1.230(5) . ?
O16 N9 1.227(5) . ?
O17 N9 1.220(5) . ?
O18 N10 1.226(5) . ?
O19 N10 1.231(5) . ?
O20 C16 1.264(6) . ?
N1 C1 1.439(6) . ?
N2 C3 1.449(6) . ?
N3 C5 1.468(6) . ?
N4 H4 0.8800 . ?
N4 N5 1.413(5) . ?
N4 C8 1.335(6) . ?
N5 H5A 0.9100 . ?
N5 H5B 0.9100 . ?
N6 H6A 0.9100 . ?
N6 H6B 0.9100 . ?
N6 N7 1.420(5) . ?
N7 H7 0.8800 . ?
N7 C9 1.328(6) . ?
N8 C11 1.456(6) . ?
N9 C13 1.449(6) . ?
N10 C15 1.457(6) . ?
C1 C2 1.385(7) . ?
C1 C6 1.404(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(6) . ?
C3 C4 1.450(6) . ?
C4 C5 1.443(6) . ?
C5 C6 1.351(7) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C10 H10C 0.9800 . ?
C10 H10D 0.9800 . ?
C10 H10E 0.9800 . ?
C11 C12 1.373(7) . ?
C11 C16 1.441(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(6) . ?
C13 C14 1.393(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.367(6) . ?
C15 C16 1.444(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O9 Cu01 O10 82.81(13) . . ?
O9 Cu01 O11 96.33(14) . . ?
O9 Cu01 N5 83.28(15) . . ?
O9 Cu01 N6 98.52(15) . . ?
O10 Cu01 O11 177.91(13) . . ?
O12 Cu01 O9 178.01(14) . . ?
O12 Cu01 O10 95.54(14) . . ?
O12 Cu01 O11 85.29(14) . . ?
O12 Cu01 N5 95.54(15) . . ?
O12 Cu01 N6 82.64(15) . . ?
N5 Cu01 O10 86.77(15) . . ?
N5 Cu01 O11 91.24(15) . . ?
N5 Cu01 N6 178.06(16) . . ?
N6 Cu01 O10 92.73(15) . . ?
N6 Cu01 O11 89.27(15) . . ?
C8 O8 C7 117.3(4) . . ?
C8 O9 Cu01 109.7(3) . . ?
Cu01 O10 H10A 133.6 . . ?
Cu01 O10 H10B 126.2 . . ?
H10A O10 H10B 98.4 . . ?
Cu01 O11 H11A 116.5 . . ?
Cu01 O11 H11B 84.3 . . ?
H11A O11 H11B 111.4 . . ?
C9 O12 Cu01 110.8(3) . . ?
C9 O13 C10 114.8(4) . . ?
O1 N1 C1 118.6(4) . . ?
O2 N1 O1 122.4(5) . . ?
O2 N1 C1 119.0(4) . . ?
O3 N2 O4 122.1(4) . . ?
O3 N2 C3 118.1(4) . . ?
O4 N2 C3 119.8(4) . . ?
O6 N3 O7 124.2(4) . . ?
O6 N3 C5 119.1(4) . . ?
O7 N3 C5 116.7(4) . . ?
N5 N4 H4 122.1 . . ?
C8 N4 H4 122.1 . . ?
C8 N4 N5 115.8(4) . . ?
Cu01 N5 H5A 110.3 . . ?
Cu01 N5 H5B 110.3 . . ?
N4 N5 Cu01 107.1(3) . . ?
N4 N5 H5A 110.3 . . ?
N4 N5 H5B 110.3 . . ?
H5A N5 H5B 108.5 . . ?
Cu01 N6 H6A 110.3 . . ?
Cu01 N6 H6B 110.3 . . ?
H6A N6 H6B 108.6 . . ?
N7 N6 Cu01 106.9(3) . . ?
N7 N6 H6A 110.3 . . ?
N7 N6 H6B 110.3 . . ?
N6 N7 H7 122.4 . . ?
C9 N7 N6 115.1(4) . . ?
C9 N7 H7 122.4 . . ?
O14 N8 O15 122.7(4) . . ?
O14 N8 C11 118.1(4) . . ?
O15 N8 C11 119.1(4) . . ?
O16 N9 C13 117.9(4) . . ?
O17 N9 O16 123.9(4) . . ?
O17 N9 C13 118.2(4) . . ?
O18 N10 O19 123.8(4) . . ?
O18 N10 C15 117.8(4) . . ?
O19 N10 C15 118.4(4) . . ?
C2 C1 N1 119.5(4) . . ?
C2 C1 C6 120.8(5) . . ?
C6 C1 N1 119.6(4) . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.1(5) . . ?
C3 C2 H2 120.4 . . ?
N2 C3 C4 119.8(4) . . ?
C2 C3 N2 116.3(4) . . ?
C2 C3 C4 123.8(4) . . ?
O5 C4 C3 125.7(4) . . ?
O5 C4 C5 122.7(4) . . ?
C5 C4 C3 111.5(4) . . ?
C4 C5 N3 116.8(4) . . ?
C6 C5 N3 117.3(4) . . ?
C6 C5 C4 125.8(4) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 C1 118.6(5) . . ?
C5 C6 H6 120.7 . . ?
O8 C7 H7A 109.5 . . ?
O8 C7 H7B 109.5 . . ?
O8 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O8 C8 N4 113.2(4) . . ?
O9 C8 O8 123.4(4) . . ?
O9 C8 N4 123.4(4) . . ?
O12 C9 O13 122.2(4) . . ?
O12 C9 N7 124.1(4) . . ?
N7 C9 O13 113.6(4) . . ?
O13 C10 H10C 109.5 . . ?
O13 C10 H10D 109.5 . . ?
O13 C10 H10E 109.5 . . ?
H10C C10 H10D 109.5 . . ?
H10C C10 H10E 109.5 . . ?
H10D C10 H10E 109.5 . . ?
C12 C11 N8 116.0(4) . . ?
C12 C11 C16 124.1(4) . . ?
C16 C11 N8 119.9(4) . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 119.1(4) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 N9 119.1(4) . . ?
C12 C13 C14 121.3(4) . . ?
C14 C13 N9 119.5(4) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 C13 118.3(4) . . ?
C15 C14 H14 120.8 . . ?
C14 C15 N10 117.3(4) . . ?
C14 C15 C16 124.9(4) . . ?
C16 C15 N10 117.8(4) . . ?
O20 C16 C11 124.6(4) . . ?
O20 C16 C15 123.5(4) . . ?
C11 C16 C15 111.9(4) . . ?

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
Cu01 O9 C8 O8 -171.7(4) . . . . ?
Cu01 O9 C8 N4 8.8(6) . . . . ?
Cu01 O12 C9 O13 176.1(4) . . . . ?
Cu01 O12 C9 N7 -4.6(6) . . . . ?
Cu01 N6 N7 C9 -5.8(5) . . . . ?
O1 N1 C1 C2 173.4(5) . . . . ?
O1 N1 C1 C6 -10.7(7) . . . . ?
O2 N1 C1 C2 -6.7(7) . . . . ?
O2 N1 C1 C6 169.2(5) . . . . ?
O3 N2 C3 C2 19.6(7) . . . . ?
O3 N2 C3 C4 -157.3(5) . . . . ?
O4 N2 C3 C2 -161.2(4) . . . . ?
O4 N2 C3 C4 21.9(7) . . . . ?
O5 C4 C5 N3 3.5(7) . . . . ?
O5 C4 C5 C6 -179.1(5) . . . . ?
O6 N3 C5 C4 -48.8(6) . . . . ?
O6 N3 C5 C6 133.5(5) . . . . ?
O7 N3 C5 C4 132.5(5) . . . . ?
O7 N3 C5 C6 -45.2(6) . . . . ?
O14 N8 C11 C12 -147.2(4) . . . . ?
O14 N8 C11 C16 32.8(6) . . . . ?
O15 N8 C11 C12 30.3(6) . . . . ?
O15 N8 C11 C16 -149.7(4) . . . . ?
O16 N9 C13 C12 6.1(7) . . . . ?
O16 N9 C13 C14 -172.7(5) . . . . ?
O17 N9 C13 C12 -172.9(5) . . . . ?
O17 N9 C13 C14 8.2(7) . . . . ?
O18 N10 C15 C14 44.6(6) . . . . ?
O18 N10 C15 C16 -133.3(5) . . . . ?
O19 N10 C15 C14 -134.2(5) . . . . ?
O19 N10 C15 C16 48.0(6) . . . . ?
N1 C1 C2 C3 -179.3(4) . . . . ?
N1 C1 C6 C5 -180.0(4) . . . . ?
N2 C3 C4 O5 -3.3(7) . . . . ?
N2 C3 C4 C5 172.9(4) . . . . ?
N3 C5 C6 C1 176.5(4) . . . . ?
N5 N4 C8 O8 170.6(4) . . . . ?
N5 N4 C8 O9 -9.9(7) . . . . ?
N6 N7 C9 O12 7.5(7) . . . . ?
N6 N7 C9 O13 -173.2(4) . . . . ?
N8 C11 C12 C13 175.1(4) . . . . ?
N8 C11 C16 O20 8.2(7) . . . . ?
N8 C11 C16 C15 -172.3(4) . . . . ?
N9 C13 C14 C15 -177.2(4) . . . . ?
N10 C15 C16 O20 -7.7(7) . . . . ?
N10 C15 C16 C11 172.8(4) . . . . ?
C1 C2 C3 N2 -177.4(4) . . . . ?
C1 C2 C3 C4 -0.7(7) . . . . ?
C2 C1 C6 C5 -4.1(7) . . . . ?
C2 C3 C4 O5 -180.0(5) . . . . ?
C2 C3 C4 C5 -3.7(7) . . . . ?
C3 C4 C5 N3 -172.9(4) . . . . ?
C3 C4 C5 C6 4.5(7) . . . . ?
C4 C5 C6 C1 -0.9(8) . . . . ?
C6 C1 C2 C3 4.8(7) . . . . ?
C7 O8 C8 O9 8.7(7) . . . . ?
C7 O8 C8 N4 -171.8(4) . . . . ?
C8 N4 N5 Cu01 5.0(5) . . . . ?
C10 O13 C9 O12 -2.2(7) . . . . ?
C10 O13 C9 N7 178.4(4) . . . . ?
C11 C12 C13 N9 179.8(4) . . . . ?
C11 C12 C13 C14 -1.4(7) . . . . ?
C12 C11 C16 O20 -171.8(5) . . . . ?
C12 C11 C16 C15 7.6(7) . . . . ?
C12 C13 C14 C15 4.0(7) . . . . ?
C13 C14 C15 N10 -178.2(4) . . . . ?
C13 C14 C15 C16 -0.5(7) . . . . ?
C14 C15 C16 O20 174.6(5) . . . . ?
C14 C15 C16 C11 -4.9(7) . . . . ?
C16 C11 C12 C13 -4.9(7) . . . . ?

_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_bwn18210
_database_code_depnum_ccdc_archive 'CCDC 1881675'
loop_
_audit_author_name
_audit_author_address
'Xiaoming Yang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2018-11-27 deposited with the CCDC.	2019-08-06 downloaded from the CCDC.
;
_audit_creation_date             2018-08-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H16 N4 O6 Zn, 2(C6 H2 N3 O7)'
_chemical_formula_sum            'C16 H20 N10 O20 Zn'
_chemical_formula_weight         737.79
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1016(14)
_cell_length_b                   7.9404(16)
_cell_length_c                   12.364(3)
_cell_angle_alpha                96.25(3)
_cell_angle_beta                 92.51(3)
_cell_angle_gamma                105.12(3)
_cell_volume                     667.2(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2399
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      2.6781
_shelx_estimated_absorpt_T_max   0.860
_shelx_estimated_absorpt_T_min   0.812
_exptl_absorpt_coefficient_mu    1.035
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6521
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         2.678
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega 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                2909
_reflns_number_total             3012
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3012
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.067
_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)+(0.0424P)²+0.4967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0925
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
O6A \\sim O6: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.01
Uanis(O6A) \\sim Ueq, Uanis(O6) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
3. Others
 Sof(O6A)=1-FVAR(1)
 Sof(O6)=FVAR(1)
4.a Riding coordinates:
 O10(H10A,H10B), N5(H5A,H5B), N4(H4)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
4.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.500000 0.500000 0.000000 0.01564(11) Uani 1 2 d S T P . .
O8 O 0.25360(19) 0.37329(18) 0.07638(11) 0.0172(3) Uani 1 1 d . . . . .
O9 O -0.0617(2) 0.2201(2) 0.03286(12) 0.0230(3) Uani 1 1 d . . . . .
O1 O 0.2590(2) 0.7722(2) 0.21453(11) 0.0228(3) Uani 1 1 d . . . . .
O10 O 0.4893(2) 0.75963(18) 0.05128(12) 0.0205(3) Uani 1 1 d . . . . .
H10A H 0.489383 0.822939 0.001076 0.025 Uiso 1 1 d R . . . .
H10B H 0.417653 0.781249 0.100286 0.025 Uiso 1 1 d R . . . .
O2 O 0.0035(3) 0.5178(2) 0.31297(14) 0.0324(4) Uani 1 1 d . . . . .
O3 O 0.1918(3) 0.5125(2) 0.45508(14) 0.0306(4) Uani 1 1 d . . . . .
O5 O 0.3581(3) 1.3089(2) 0.63670(13) 0.0324(4) Uani 1 1 d . . . A 1
O4 O 0.1825(3) 1.0729(2) 0.69244(13) 0.0353(4) Uani 1 1 d . . . . .
O7 O 0.4282(3) 1.0842(2) 0.15266(13) 0.0320(4) Uani 1 1 d . . . . .
N1 N 0.1256(3) 0.5902(2) 0.38853(14) 0.0202(3) Uani 1 1 d . . . . .
N5 N 0.2775(2) 0.4646(2) -0.12820(13) 0.0174(3) Uani 1 1 d . . . . .
H5A H 0.283937 0.400493 -0.186883 0.021 Uiso 1 1 d R . . . .
H5B H 0.267797 0.565683 -0.139753 0.021 Uiso 1 1 d R . . . .
N2 N 0.2715(3) 1.1516(2) 0.62180(14) 0.0217(4) Uani 1 1 d . . . . .
N4 N 0.1007(2) 0.3676(2) -0.09074(14) 0.0200(3) Uani 1 1 d . . . . .
H4 H 0.002277 0.320543 -0.135759 0.024 Uiso 1 1 d R . . . .
N3 N 0.4527(3) 1.1486(2) 0.24800(14) 0.0223(4) Uani 1 1 d . . . . .
O6 O 0.5751(9) 1.2866(5) 0.2781(2) 0.0376(12) Uani 0.804(17) 1 d . U . B 1
C2 C 0.1962(3) 0.7824(2) 0.40110(16) 0.0160(4) Uani 1 1 d . . . . .
C6 C 0.3528(3) 1.0492(3) 0.33071(15) 0.0168(4) Uani 1 1 d . . . . .
C3 C 0.1965(3) 0.8706(3) 0.50214(15) 0.0167(4) Uani 1 1 d . . . . .
H3 H 0.147657 0.809802 0.561406 0.020 Uiso 1 1 calc R . . . .
C1 C 0.2668(3) 0.8623(3) 0.30542(15) 0.0158(4) Uani 1 1 d . . . . .
C7 C 0.1082(3) 0.3235(2) 0.01079(15) 0.0161(4) Uani 1 1 d . . . . .
C8 C -0.0584(3) 0.1392(3) 0.13254(17) 0.0231(4) Uani 1 1 d . . . . .
H8A H 0.036305 0.068702 0.129079 0.035 Uiso 1 1 calc GR . . . .
H8B H -0.188726 0.063241 0.140577 0.035 Uiso 1 1 calc GR . . . .
H8C H -0.020426 0.230960 0.195201 0.035 Uiso 1 1 calc GR . . . .
C4 C 0.2713(3) 1.0537(3) 0.51571(15) 0.0166(4) Uani 1 1 d . . . . .
C5 C 0.3530(3) 1.1424(3) 0.43207(16) 0.0170(4) Uani 1 1 d . . . . .
H5 H 0.408767 1.266012 0.443866 0.020 Uiso 1 1 calc R . . . .
O6A O 0.493(4) 1.326(2) 0.2774(10) 0.038(4) Uani 0.196(17) 1 d . U . B 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 O8 2.0975(15) 2_665 ?
Zn1 O8 2.0975(15) . ?
Zn1 O10 2.1116(15) . ?
Zn1 O10 2.1116(15) 2_665 ?
Zn1 N5 2.1307(18) . ?
Zn1 N5 2.1307(18) 2_665 ?
O8 C7 1.235(2) . ?
O9 C7 1.328(2) . ?
O9 C8 1.453(2) . ?
O1 C1 1.256(2) . ?
O10 H10A 0.8401 . ?
O10 H10B 0.8400 . ?
O2 N1 1.228(2) . ?
O3 N1 1.227(2) . ?
O5 N2 1.229(2) . ?
O4 N2 1.231(2) . ?
O7 N3 1.219(2) . ?
N1 C2 1.465(2) . ?
N5 H5A 0.8499 . ?
N5 H5B 0.8499 . ?
N5 N4 1.417(2) . ?
N2 C4 1.450(2) . ?
N4 H4 0.8500 . ?
N4 C7 1.342(2) . ?
N3 O6 1.217(3) . ?
N3 C6 1.455(2) . ?
N3 O6A 1.366(18) . ?
C2 C3 1.364(3) . ?
C2 C1 1.450(3) . ?
C6 C1 1.443(3) . ?
C6 C5 1.384(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.400(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C4 C5 1.379(3) . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O8 Zn1 O8 180.0 2_665 . ?
O8 Zn1 O10 96.64(6) . . ?
O8 Zn1 O10 83.36(6) 2_665 . ?
O8 Zn1 O10 83.36(6) . 2_665 ?
O8 Zn1 O10 96.64(6) 2_665 2_665 ?
O8 Zn1 N5 79.60(6) 2_665 2_665 ?
O8 Zn1 N5 100.40(6) . 2_665 ?
O8 Zn1 N5 79.60(6) . . ?
O8 Zn1 N5 100.40(6) 2_665 . ?
O10 Zn1 O10 180.00(8) 2_665 . ?
O10 Zn1 N5 87.37(7) . 2_665 ?
O10 Zn1 N5 87.37(7) 2_665 . ?
O10 Zn1 N5 92.63(7) . . ?
O10 Zn1 N5 92.63(7) 2_665 2_665 ?
N5 Zn1 N5 180.0 2_665 . ?
C7 O8 Zn1 110.80(12) . . ?
C7 O9 C8 115.56(16) . . ?
Zn1 O10 H10A 115.2 . . ?
Zn1 O10 H10B 121.3 . . ?
H10A O10 H10B 111.5 . . ?
O2 N1 C2 118.04(17) . . ?
O3 N1 O2 124.40(18) . . ?
O3 N1 C2 117.56(17) . . ?
Zn1 N5 H5A 118.3 . . ?
Zn1 N5 H5B 107.8 . . ?
H5A N5 H5B 112.2 . . ?
N4 N5 Zn1 106.99(11) . . ?
N4 N5 H5A 101.2 . . ?
N4 N5 H5B 109.8 . . ?
O5 N2 O4 123.15(18) . . ?
O5 N2 C4 118.80(17) . . ?
O4 N2 C4 118.05(18) . . ?
N5 N4 H4 119.9 . . ?
C7 N4 N5 117.28(16) . . ?
C7 N4 H4 121.4 . . ?
O7 N3 C6 119.85(18) . . ?
O7 N3 O6A 121.8(6) . . ?
O6 N3 O7 121.5(2) . . ?
O6 N3 C6 118.2(2) . . ?
O6A N3 C6 112.1(6) . . ?
C3 C2 N1 117.58(17) . . ?
C3 C2 C1 125.48(18) . . ?
C1 C2 N1 116.90(17) . . ?
C1 C6 N3 119.68(17) . . ?
C5 C6 N3 116.48(17) . . ?
C5 C6 C1 123.80(17) . . ?
C2 C3 H3 121.1 . . ?
C2 C3 C4 117.85(17) . . ?
C4 C3 H3 121.1 . . ?
O1 C1 C2 121.75(18) . . ?
O1 C1 C6 126.37(17) . . ?
C6 C1 C2 111.79(17) . . ?
O8 C7 O9 123.79(17) . . ?
O8 C7 N4 124.63(18) . . ?
O9 C7 N4 111.58(17) . . ?
O9 C8 H8A 109.5 . . ?
O9 C8 H8B 109.5 . . ?
O9 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C4 N2 119.21(17) . . ?
C5 C4 N2 119.11(18) . . ?
C5 C4 C3 121.61(18) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 C6 119.20(18) . . ?
C4 C5 H5 120.4 . . ?

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 O8 C7 O9 171.01(15) . . . . ?
Zn1 O8 C7 N4 -9.6(2) . . . . ?
Zn1 N5 N4 C7 1.0(2) . . . . ?
O2 N1 C2 C3 130.6(2) . . . . ?
O2 N1 C2 C1 -51.7(2) . . . . ?
O3 N1 C2 C3 -48.8(2) . . . . ?
O3 N1 C2 C1 128.89(19) . . . . ?
O5 N2 C4 C3 171.34(19) . . . . ?
O5 N2 C4 C5 -5.7(3) . . . . ?
O4 N2 C4 C3 -9.4(3) . . . . ?
O4 N2 C4 C5 173.57(18) . . . . ?
O7 N3 C6 C1 15.7(3) . . . . ?
O7 N3 C6 C5 -166.46(19) . . . . ?
N1 C2 C3 C4 177.43(17) . . . . ?
N1 C2 C1 O1 3.5(3) . . . . ?
N1 C2 C1 C6 -173.35(16) . . . . ?
N5 N4 C7 O8 6.1(3) . . . . ?
N5 N4 C7 O9 -174.43(16) . . . . ?
N2 C4 C5 C6 -179.95(17) . . . . ?
N3 C6 C1 O1 -4.0(3) . . . . ?
N3 C6 C1 C2 172.71(16) . . . . ?
N3 C6 C5 C4 -176.08(16) . . . . ?
O6 N3 C6 C1 -156.4(4) . . . . ?
O6 N3 C6 C5 21.4(5) . . . . ?
C2 C3 C4 N2 179.23(17) . . . . ?
C2 C3 C4 C5 -3.8(3) . . . . ?
C3 C2 C1 O1 -178.96(19) . . . . ?
C3 C2 C1 C6 4.2(3) . . . . ?
C3 C4 C5 C6 3.1(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1 C6 C5 C4 1.6(3) . . . . ?
C8 O9 C7 O8 -11.5(3) . . . . ?
C8 O9 C7 N4 169.06(17) . . . . ?
C5 C6 C1 O1 178.39(19) . . . . ?
C5 C6 C1 C2 -4.9(3) . . . . ?
O6A N3 C6 C1 168.4(12) . . . . ?
O6A N3 C6 C5 -13.8(12) . . . . ?

_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_bwn18263
_database_code_depnum_ccdc_archive 'CCDC 1881672'
loop_
_audit_author_name
_audit_author_address
'Xiaoming Yang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2018-11-27 deposited with the CCDC.	2019-08-06 downloaded from the CCDC.
;
_audit_creation_date             2018-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H16 Fe N4 O6, 2(C6 H2 N3 O7)'
_chemical_formula_sum            'C16 H20 Fe N10 O20'
_chemical_formula_weight         728.27
_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'
Fe Fe 0.3463 0.8444 '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           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                   14.392(3)
_cell_length_b                   7.9132(16)
_cell_length_c                   24.259(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.34(3)
_cell_angle_gamma                90
_cell_volume                     2708.9(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4517
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      1.7123
_shelx_estimated_absorpt_T_max   0.883
_shelx_estimated_absorpt_T_min   0.861
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10572
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         2.887
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega 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                2903
_reflns_number_total             3080
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3080
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.112
_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)+(0.0420P)²+4.6196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1029
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O10(H10A,H10B)
2.b Secondary CH2 refined with riding coordinates:
 N5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4A), C4(H4), C2(H2)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.500000 0.70530(5) 0.250000 0.01609(12) Uani 1 2 d S T P . .
O9 O 0.44441(10) 0.52445(19) 0.30018(6) 0.0216(3) Uani 1 1 d . . . . .
O7 O 0.32277(10) 0.8315(2) 0.35333(6) 0.0212(3) Uani 1 1 d . . . . .
O10 O 0.45126(10) 0.90702(19) 0.29231(6) 0.0224(3) Uani 1 1 d . . . . .
H10A H 0.418379 0.886184 0.316542 0.027 Uiso 1 1 d R . . . .
H10B H 0.496579 0.963654 0.310352 0.027 Uiso 1 1 d R . . . .
O5 O 0.55966(10) 0.8437(2) 0.48281(7) 0.0283(4) Uani 1 1 d . . . . .
O3 O 0.26743(12) 0.3831(2) 0.55649(7) 0.0330(4) Uani 1 1 d . . . . .
O6 O 0.48160(12) 0.9816(2) 0.41183(7) 0.0307(4) Uani 1 1 d . . . . .
O4 O 0.41314(12) 0.4625(2) 0.58602(7) 0.0319(4) Uani 1 1 d . . . . .
O2 O 0.14119(11) 0.4798(2) 0.35173(7) 0.0314(4) Uani 1 1 d . . . . .
O8 O 0.32315(11) 0.3486(2) 0.30333(7) 0.0295(4) Uani 1 1 d . . . . .
O1 O 0.13052(12) 0.7508(2) 0.34259(8) 0.0385(4) Uani 1 1 d . . . . .
N2 N 0.33842(13) 0.4611(2) 0.55049(7) 0.0231(4) Uani 1 1 d . . . . .
N1 N 0.16990(12) 0.6238(2) 0.36447(7) 0.0213(4) Uani 1 1 d . . . . .
N4 N 0.31514(12) 0.5175(2) 0.22923(7) 0.0223(4) Uani 1 1 d . . . . .
H4A H 0.257403 0.480069 0.216246 0.027 Uiso 1 1 calc R . . . .
N3 N 0.48758(12) 0.8678(2) 0.44678(7) 0.0201(4) Uani 1 1 d . . . . .
N5 N 0.36009(11) 0.6354(2) 0.19918(7) 0.0191(4) Uani 1 1 d . . . . .
H5A H 0.323357 0.729306 0.191487 0.023 Uiso 1 1 calc R . . . .
H5B H 0.367725 0.589231 0.165997 0.023 Uiso 1 1 calc R . . . .
C4 C 0.40942(14) 0.6637(3) 0.49488(8) 0.0191(4) Uani 1 1 d . . . . .
H4 H 0.462995 0.670619 0.524735 0.023 Uiso 1 1 calc R . . . .
C8 C 0.36621(14) 0.4665(3) 0.27876(9) 0.0191(4) Uani 1 1 d . . . . .
C3 C 0.33483(14) 0.5579(3) 0.49941(8) 0.0191(4) Uani 1 1 d . . . . .
C5 C 0.40593(13) 0.7591(3) 0.44704(8) 0.0176(4) Uani 1 1 d . . . . .
C1 C 0.25356(13) 0.6420(3) 0.40915(8) 0.0181(4) Uani 1 1 d . . . . .
C2 C 0.25566(14) 0.5445(3) 0.45624(9) 0.0195(4) Uani 1 1 d . . . . .
H2 H 0.204876 0.470577 0.459234 0.023 Uiso 1 1 calc R . . . .
C6 C 0.32744(13) 0.7553(3) 0.39927(8) 0.0169(4) Uani 1 1 d . . . . .
C7 C 0.37715(16) 0.2854(3) 0.35637(10) 0.0298(5) Uani 1 1 d . . . . .
H7A H 0.440298 0.250679 0.351328 0.045 Uiso 1 1 calc GR . . . .
H7B H 0.344248 0.188259 0.368685 0.045 Uiso 1 1 calc GR . . . .
H7C H 0.383264 0.374796 0.384826 0.045 Uiso 1 1 calc GR . . . .


_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
Fe1 O9 2.1337(15) 2_655 ?
Fe1 O9 2.1337(15) . ?
Fe1 O10 2.0921(15) . ?
Fe1 O10 2.0921(15) 2_655 ?
Fe1 N5 2.2147(17) . ?
Fe1 N5 2.2147(18) 2_655 ?
O9 C8 1.232(2) . ?
O7 C6 1.257(2) . ?
O10 H10A 0.8402 . ?
O10 H10B 0.8400 . ?
O5 N3 1.233(2) . ?
O3 N2 1.227(2) . ?
O6 N3 1.228(2) . ?
O4 N2 1.239(2) . ?
O2 N1 1.231(2) . ?
O8 C8 1.324(3) . ?
O8 C7 1.455(3) . ?
O1 N1 1.223(2) . ?
N2 C3 1.449(3) . ?
N1 C1 1.460(3) . ?
N4 H4A 0.8800 . ?
N4 N5 1.416(2) . ?
N4 C8 1.341(3) . ?
N3 C5 1.458(3) . ?
N5 H5A 0.9100 . ?
N5 H5B 0.9100 . ?
C4 H4 0.9500 . ?
C4 C3 1.383(3) . ?
C4 C5 1.377(3) . ?
C3 C2 1.392(3) . ?
C5 C6 1.451(3) . ?
C1 C2 1.374(3) . ?
C1 C6 1.446(3) . ?
C2 H2 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

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
O9 Fe1 O9 95.76(9) 2_655 . ?
O9 Fe1 N5 75.41(6) . . ?
O9 Fe1 N5 85.22(6) . 2_655 ?
O9 Fe1 N5 85.22(6) 2_655 . ?
O9 Fe1 N5 75.41(6) 2_655 2_655 ?
O10 Fe1 O9 91.86(6) 2_655 2_655 ?
O10 Fe1 O9 91.86(6) . . ?
O10 Fe1 O9 172.37(6) . 2_655 ?
O10 Fe1 O9 172.37(6) 2_655 . ?
O10 Fe1 O10 80.54(8) . 2_655 ?
O10 Fe1 N5 105.87(6) . 2_655 ?
O10 Fe1 N5 96.20(6) 2_655 2_655 ?
O10 Fe1 N5 96.20(6) . . ?
O10 Fe1 N5 105.86(6) 2_655 . ?
N5 Fe1 N5 151.06(10) 2_655 . ?
C8 O9 Fe1 115.03(13) . . ?
Fe1 O10 H10A 118.9 . . ?
Fe1 O10 H10B 111.2 . . ?
H10A O10 H10B 103.1 . . ?
C8 O8 C7 115.11(16) . . ?
O3 N2 O4 123.44(19) . . ?
O3 N2 C3 118.49(18) . . ?
O4 N2 C3 118.07(18) . . ?
O2 N1 C1 117.70(18) . . ?
O1 N1 O2 123.24(18) . . ?
O1 N1 C1 119.04(18) . . ?
N5 N4 H4A 122.1 . . ?
C8 N4 H4A 122.1 . . ?
C8 N4 N5 115.72(16) . . ?
O5 N3 C5 118.19(17) . . ?
O6 N3 O5 122.53(18) . . ?
O6 N3 C5 119.26(17) . . ?
Fe1 N5 H5A 109.8 . . ?
Fe1 N5 H5B 109.8 . . ?
N4 N5 Fe1 109.59(12) . . ?
N4 N5 H5A 109.8 . . ?
N4 N5 H5B 109.8 . . ?
H5A N5 H5B 108.2 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 119.90(19) . . ?
O9 C8 O8 122.81(19) . . ?
O9 C8 N4 124.07(19) . . ?
O8 C8 N4 113.11(17) . . ?
C4 C3 N2 119.36(18) . . ?
C4 C3 C2 121.34(18) . . ?
C2 C3 N2 119.30(18) . . ?
C4 C5 N3 115.55(18) . . ?
C4 C5 C6 123.75(19) . . ?
C6 C5 N3 120.70(18) . . ?
C2 C1 N1 116.24(18) . . ?
C2 C1 C6 126.10(18) . . ?
C6 C1 N1 117.63(18) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 C3 117.63(18) . . ?
C1 C2 H2 121.2 . . ?
O7 C6 C5 126.56(18) . . ?
O7 C6 C1 122.09(18) . . ?
C1 C6 C5 111.27(17) . . ?
O8 C7 H7A 109.5 . . ?
O8 C7 H7B 109.5 . . ?
O8 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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
Fe1 O9 C8 O8 177.52(16) . . . . ?
Fe1 O9 C8 N4 -3.9(3) . . . . ?
O5 N3 C5 C4 13.8(3) . . . . ?
O5 N3 C5 C6 -166.32(19) . . . . ?
O3 N2 C3 C4 171.8(2) . . . . ?
O3 N2 C3 C2 -7.2(3) . . . . ?
O6 N3 C5 C4 -164.61(19) . . . . ?
O6 N3 C5 C6 15.3(3) . . . . ?
O4 N2 C3 C4 -7.8(3) . . . . ?
O4 N2 C3 C2 173.2(2) . . . . ?
O2 N1 C1 C2 -44.6(3) . . . . ?
O2 N1 C1 C6 133.3(2) . . . . ?
O1 N1 C1 C2 133.6(2) . . . . ?
O1 N1 C1 C6 -48.5(3) . . . . ?
N2 C3 C2 C1 178.12(18) . . . . ?
N1 C1 C2 C3 179.50(18) . . . . ?
N1 C1 C6 O7 -2.7(3) . . . . ?
N1 C1 C6 C5 -179.56(17) . . . . ?
N3 C5 C6 O7 4.7(3) . . . . ?
N3 C5 C6 C1 -178.68(17) . . . . ?
N5 N4 C8 O9 5.3(3) . . . . ?
N5 N4 C8 O8 -176.01(17) . . . . ?
C4 C3 C2 C1 -0.9(3) . . . . ?
C4 C5 C6 O7 -175.5(2) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C8 N4 N5 Fe1 -3.6(2) . . . . ?
C3 C4 C5 N3 179.29(18) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C5 C4 C3 N2 -178.62(18) . . . . ?
C5 C4 C3 C2 0.4(3) . . . . ?
C2 C1 C6 O7 175.05(19) . . . . ?
C2 C1 C6 C5 -1.8(3) . . . . ?
C6 C1 C2 C3 1.7(3) . . . . ?
C7 O8 C8 O9 -3.1(3) . . . . ?
C7 O8 C8 N4 178.13(19) . . . . ?

_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_bwn18185
_database_code_depnum_ccdc_archive 'CCDC 1881674'
loop_
_audit_author_name
_audit_author_address
'Xiaoming Yang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2018-11-27 deposited with the CCDC.	2019-08-06 downloaded from the CCDC.
;
_audit_creation_date             2018-07-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H16 N4 Ni O6, 2(C6 H2 N3 O7)'
_chemical_formula_sum            'C16 H20 N10 Ni O20'
_chemical_formula_weight         731.13
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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           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                   14.276(3)
_cell_length_b                   7.9662(16)
_cell_length_c                   24.212(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.04(3)
_cell_angle_gamma                90
_cell_volume                     2702.5(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5017
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      31.2514
_cell_measurement_theta_min      1.7139
_shelx_estimated_absorpt_T_max   0.872
_shelx_estimated_absorpt_T_min   0.832
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            11532
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.535
_diffrn_reflns_theta_min         2.908
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega 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                3538
_reflns_number_total             4027
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         4027
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      1.082
_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)+(0.0480P)²+6.7028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1306
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O3(H3A,H3B), N1(H1A,H1B), N2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.500000 0.68952(5) 0.250000 0.01582(12) Uani 1 2 d S T P . .
O1 O 0.44690(12) 0.5153(2) 0.29813(7) 0.0207(3) Uani 1 1 d . . . . .
O2 O 0.32357(13) 0.3398(2) 0.29728(8) 0.0292(4) Uani 1 1 d . . . . .
O3 O 0.54520(12) 0.8827(2) 0.20644(7) 0.0215(3) Uani 1 1 d . . . . .
H3A H 0.501259 0.945067 0.189818 0.026 Uiso 1 1 d R . . . .
H3B H 0.585009 0.864937 0.185658 0.026 Uiso 1 1 d R . . . .
N1 N 0.36446(14) 0.6454(3) 0.19989(8) 0.0179(4) Uani 1 1 d . . . . .
H1A H 0.330418 0.733417 0.193672 0.021 Uiso 1 1 d R . . . .
H1B H 0.370358 0.605607 0.168152 0.021 Uiso 1 1 d R . . . .
N2 N 0.31853(14) 0.5191(3) 0.22626(9) 0.0218(4) Uani 1 1 d . . . . .
H2 H 0.280272 0.456107 0.204282 0.026 Uiso 1 1 d R . . . .
C1 C 0.36832(16) 0.4606(3) 0.27506(10) 0.0191(4) Uani 1 1 d . . . . .
C2 C 0.37555(19) 0.2707(4) 0.34982(12) 0.0299(6) Uani 1 1 d . . . . .
H2A H 0.439896 0.238510 0.345273 0.045 Uiso 1 1 calc GR . . . .
H2B H 0.341880 0.171624 0.360032 0.045 Uiso 1 1 calc GR . . . .
H2C H 0.379931 0.355269 0.379595 0.045 Uiso 1 1 calc GR . . . .
O002 O 0.32158(12) 0.8284(2) 0.35420(7) 0.0216(3) Uani 1 1 d . . . . .
O4 O 0.12863(14) 0.7457(3) 0.34499(10) 0.0396(5) Uani 1 1 d . . . . .
O5 O 0.14211(14) 0.4763(3) 0.35235(9) 0.0330(5) Uani 1 1 d . . . . .
O6 O 0.26884(15) 0.3824(3) 0.55851(8) 0.0344(5) Uani 1 1 d . . . . .
O7 O 0.41583(15) 0.4607(3) 0.58705(8) 0.0320(4) Uani 1 1 d . . . . .
O8 O 0.56052(13) 0.8445(3) 0.48278(8) 0.0288(4) Uani 1 1 d . . . . .
O9 O 0.48021(14) 0.9818(2) 0.41252(8) 0.0309(4) Uani 1 1 d . . . . .
N3 N 0.16935(14) 0.6200(3) 0.36583(9) 0.0214(4) Uani 1 1 d . . . . .
N4 N 0.34054(16) 0.4602(3) 0.55207(9) 0.0237(4) Uani 1 1 d . . . . .
N5 N 0.48752(15) 0.8677(3) 0.44725(8) 0.0206(4) Uani 1 1 d . . . . .
C3 C 0.25336(16) 0.6383(3) 0.41057(10) 0.0186(4) Uani 1 1 d . . . . .
C4 C 0.25657(17) 0.5417(3) 0.45780(10) 0.0201(4) Uani 1 1 d . . . . .
H4 H 0.206113 0.466822 0.461034 0.024 Uiso 1 1 calc R . . . .
C5 C 0.33595(17) 0.5569(3) 0.50074(9) 0.0201(4) Uani 1 1 d . . . . .
C6 C 0.41045(17) 0.6629(3) 0.49604(10) 0.0201(4) Uani 1 1 d . . . . .
H6 H 0.464390 0.670520 0.525768 0.024 Uiso 1 1 calc R . . . .
C7 C 0.40625(16) 0.7580(3) 0.44789(10) 0.0187(4) Uani 1 1 d . . . . .
C8 C 0.32676(16) 0.7526(3) 0.40053(9) 0.0166(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 2.0485(17) . ?
Ni1 O1 2.0485(17) 2_655 ?
Ni1 O3 2.0390(17) . ?
Ni1 O3 2.0390(17) 2_655 ?
Ni1 N1 2.107(2) . ?
Ni1 N1 2.107(2) 2_655 ?
O1 C1 1.233(3) . ?
O2 C1 1.325(3) . ?
O2 C2 1.453(3) . ?
N1 N2 1.418(3) . ?
N2 C1 1.340(3) . ?
O002 C8 1.264(3) . ?
O4 N3 1.217(3) . ?
O5 N3 1.233(3) . ?
O6 N4 1.232(3) . ?
O7 N4 1.234(3) . ?
O8 N5 1.232(3) . ?
O9 N5 1.229(3) . ?
N3 C3 1.461(3) . ?
N4 C5 1.453(3) . ?
N5 C7 1.455(3) . ?
C3 C4 1.372(3) . ?
C3 C8 1.443(3) . ?
C4 C5 1.389(3) . ?
C5 C6 1.380(3) . ?
C6 C7 1.382(3) . ?
C7 C8 1.451(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 O1 94.72(10) 2_655 . ?
O1 Ni1 N1 87.63(7) 2_655 . ?
O1 Ni1 N1 87.63(7) . 2_655 ?
O1 Ni1 N1 79.36(7) . . ?
O1 Ni1 N1 79.36(7) 2_655 2_655 ?
O3 Ni1 O1 91.64(7) 2_655 . ?
O3 Ni1 O1 173.57(7) . . ?
O3 Ni1 O1 173.57(7) 2_655 2_655 ?
O3 Ni1 O1 91.65(7) . 2_655 ?
O3 Ni1 O3 82.00(10) . 2_655 ?
O3 Ni1 N1 100.07(7) . . ?
O3 Ni1 N1 94.42(7) . 2_655 ?
O3 Ni1 N1 94.42(7) 2_655 . ?
O3 Ni1 N1 100.06(7) 2_655 2_655 ?
N1 Ni1 N1 160.79(11) . 2_655 ?
C1 O1 Ni1 112.67(15) . . ?
C1 O2 C2 115.20(19) . . ?
N2 N1 Ni1 108.18(13) . . ?
C1 N2 N1 115.52(19) . . ?
O1 C1 O2 122.7(2) . . ?
O1 C1 N2 124.0(2) . . ?
O2 C1 N2 113.3(2) . . ?
O4 N3 O5 123.5(2) . . ?
O4 N3 C3 119.0(2) . . ?
O5 N3 C3 117.5(2) . . ?
O6 N4 O7 123.4(2) . . ?
O6 N4 C5 118.2(2) . . ?
O7 N4 C5 118.4(2) . . ?
O8 N5 C7 118.1(2) . . ?
O9 N5 O8 122.6(2) . . ?
O9 N5 C7 119.2(2) . . ?
C4 C3 N3 117.0(2) . . ?
C4 C3 C8 125.8(2) . . ?
C8 C3 N3 117.2(2) . . ?
C3 C4 C5 117.9(2) . . ?
C4 C5 N4 119.4(2) . . ?
C6 C5 N4 119.1(2) . . ?
C6 C5 C4 121.5(2) . . ?
C5 C6 C7 119.7(2) . . ?
C6 C7 N5 115.6(2) . . ?
C6 C7 C8 123.5(2) . . ?
C8 C7 N5 120.9(2) . . ?
O002 C8 C3 122.0(2) . . ?
O002 C8 C7 126.2(2) . . ?
C3 C8 C7 111.6(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
Ni1 O1 C1 O2 175.96(18) . . . . ?
Ni1 O1 C1 N2 -5.9(3) . . . . ?
Ni1 N1 N2 C1 0.9(2) . . . . ?
N1 N2 C1 O1 3.4(3) . . . . ?
N1 N2 C1 O2 -178.27(19) . . . . ?
C2 O2 C1 O1 -2.6(4) . . . . ?
C2 O2 C1 N2 179.1(2) . . . . ?
O4 N3 C3 C4 132.2(3) . . . . ?
O4 N3 C3 C8 -49.5(3) . . . . ?
O5 N3 C3 C4 -45.8(3) . . . . ?
O5 N3 C3 C8 132.4(2) . . . . ?
O6 N4 C5 C4 -8.3(3) . . . . ?
O6 N4 C5 C6 171.2(2) . . . . ?
O7 N4 C5 C4 172.0(2) . . . . ?
O7 N4 C5 C6 -8.5(3) . . . . ?
O8 N5 C7 C6 14.4(3) . . . . ?
O8 N5 C7 C8 -166.0(2) . . . . ?
O9 N5 C7 C6 -163.8(2) . . . . ?
O9 N5 C7 C8 15.8(3) . . . . ?
N3 C3 C4 C5 179.8(2) . . . . ?
N3 C3 C8 O002 -3.2(3) . . . . ?
N3 C3 C8 C7 -179.5(2) . . . . ?
N4 C5 C6 C7 -178.8(2) . . . . ?
N5 C7 C8 O002 5.1(4) . . . . ?
N5 C7 C8 C3 -178.8(2) . . . . ?
C3 C4 C5 N4 178.2(2) . . . . ?
C3 C4 C5 C6 -1.3(4) . . . . ?
C4 C3 C8 O002 174.8(2) . . . . ?
C4 C3 C8 C7 -1.5(3) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C5 C6 C7 N5 179.1(2) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C6 C7 C8 O002 -175.3(2) . . . . ?
C6 C7 C8 C3 0.8(3) . . . . ?
C8 C3 C4 C5 1.7(4) . . . . ?

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

data_bwn18186
_database_code_depnum_ccdc_archive 'CCDC 1881673'
loop_
_audit_author_name
_audit_author_address
'Xiaoming Yang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2018-11-27 deposited with the CCDC.	2019-08-06 downloaded from the CCDC.
;
_audit_creation_date             2018-07-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H16 Co N4 O6, 2(C6 H2 N3 O7)'
_chemical_formula_sum            'C16 H20 Co N10 O20'
_chemical_formula_weight         731.35
_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'
Co Co 0.3494 0.9721 '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           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                   14.361(3)
_cell_length_b                   7.9175(16)
_cell_length_c                   24.317(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.49(3)
_cell_angle_gamma                90
_cell_volume                     2709.5(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4499
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4855
_cell_measurement_theta_min      0.8545
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.909
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1492
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9140
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         2.952
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega 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                2934
_reflns_number_total             3086
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3086
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.070
_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)+(0.0446P)²+3.5977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.0989
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O1(H1A,H1B), N1(H1C,H1D), N2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.500000 0.30220(4) 0.750000 0.01497(11) Uani 1 2 d S T P . .
O1 O 0.45205(10) 0.10639(17) 0.79300(6) 0.0211(3) Uani 1 1 d . . . . .
H1A H 0.420006 0.126896 0.817593 0.025 Uiso 1 1 d R . . . .
H1B H 0.498726 0.054116 0.811693 0.025 Uiso 1 1 d R . . . .
O2 O 0.55498(9) 0.47819(17) 0.70027(5) 0.0209(3) Uani 1 1 d . . . . .
O3 O 0.67729(10) 0.6544(2) 0.69904(7) 0.0289(3) Uani 1 1 d . . . . .
N1 N 0.63765(11) 0.3611(2) 0.80052(6) 0.0186(3) Uani 1 1 d . . . . .
H1C H 0.624155 0.406075 0.829695 0.022 Uiso 1 1 d R . . . .
H1D H 0.677795 0.281805 0.809205 0.022 Uiso 1 1 d R . . . .
N2 N 0.68330(11) 0.4819(2) 0.77191(7) 0.0211(3) Uani 1 1 d . . . . .
H2 H 0.725489 0.546913 0.790174 0.025 Uiso 1 1 d R . . . .
C1 C 0.63301(13) 0.5356(2) 0.72256(8) 0.0186(4) Uani 1 1 d . . . . .
C2 C 0.62400(16) 0.7196(3) 0.64601(10) 0.0305(5) Uani 1 1 d . . . . .
H2A H 0.617089 0.630644 0.617469 0.046 Uiso 1 1 calc GR . . . .
H2B H 0.658087 0.815711 0.634007 0.046 Uiso 1 1 calc GR . . . .
H2C H 0.560990 0.756400 0.650876 0.046 Uiso 1 1 calc GR . . . .
O4 O 0.87085(11) 0.2510(2) 0.65633(8) 0.0375(4) Uani 1 1 d . . . . .
O5 O 0.85892(11) 0.5220(2) 0.64800(7) 0.0313(4) Uani 1 1 d . . . . .
O6 O 0.73229(11) 0.6172(2) 0.44270(6) 0.0326(4) Uani 1 1 d . . . . .
O7 O 0.58606(12) 0.5389(2) 0.41356(6) 0.0309(4) Uani 1 1 d . . . . .
O8 O 0.44026(10) 0.1563(2) 0.51699(6) 0.0270(3) Uani 1 1 d . . . . .
O9 O 0.51907(11) 0.01918(19) 0.58789(6) 0.0297(3) Uani 1 1 d . . . . .
O10 O 0.67818(9) 0.17017(18) 0.64615(5) 0.0203(3) Uani 1 1 d . . . . .
N3 N 0.83085(11) 0.3780(2) 0.63487(7) 0.0201(3) Uani 1 1 d . . . . .
N4 N 0.66103(12) 0.5395(2) 0.44878(7) 0.0222(3) Uani 1 1 d . . . . .
N5 N 0.51256(11) 0.1325(2) 0.55283(6) 0.0185(3) Uani 1 1 d . . . . .
C3 C 0.74719(12) 0.3602(2) 0.59019(8) 0.0165(4) Uani 1 1 d . . . . .
C4 C 0.74448(13) 0.4569(2) 0.54318(8) 0.0187(4) Uani 1 1 d . . . . .
H4 H 0.795168 0.531199 0.540163 0.022 Uiso 1 1 calc R . . . .
C5 C 0.66505(13) 0.4429(2) 0.49993(7) 0.0184(4) Uani 1 1 d . . . . .
C6 C 0.59023(14) 0.3371(2) 0.50455(8) 0.0187(4) Uani 1 1 d . . . . .
H6 H 0.536378 0.330093 0.474774 0.022 Uiso 1 1 calc R . . . .
C7 C 0.59401(13) 0.2416(2) 0.55261(8) 0.0164(3) Uani 1 1 d . . . . .
C8 C 0.67307(12) 0.2463(2) 0.60013(7) 0.0154(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 2.0635(14) 2_656 ?
Co1 O1 2.0635(14) . ?
Co1 O2 2.0994(14) 2_656 ?
Co1 O2 2.0994(14) . ?
Co1 N1 2.1602(17) . ?
Co1 N1 2.1602(17) 2_656 ?
O1 H1A 0.8398 . ?
O1 H1B 0.8402 . ?
O2 C1 1.230(2) . ?
O3 C1 1.327(2) . ?
O3 C2 1.457(3) . ?
N1 H1C 0.8502 . ?
N1 H1D 0.8499 . ?
N1 N2 1.418(2) . ?
N2 H2 0.8498 . ?
N2 C1 1.341(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
O4 N3 1.222(2) . ?
O5 N3 1.230(2) . ?
O6 N4 1.228(2) . ?
O7 N4 1.235(2) . ?
O8 N5 1.230(2) . ?
O9 N5 1.228(2) . ?
O10 C8 1.260(2) . ?
N3 C3 1.457(2) . ?
N4 C5 1.451(2) . ?
N5 C7 1.455(2) . ?
C3 C4 1.370(3) . ?
C3 C8 1.452(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(3) . ?
C5 C6 1.385(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(3) . ?
C7 C8 1.450(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 O1 82.59(8) 2_656 . ?
O1 Co1 O2 172.88(5) . . ?
O1 Co1 O2 90.29(6) 2_656 . ?
O1 Co1 O2 90.29(6) . 2_656 ?
O1 Co1 O2 172.88(6) 2_656 2_656 ?
O1 Co1 N1 95.18(6) 2_656 . ?
O1 Co1 N1 103.53(6) . . ?
O1 Co1 N1 95.18(6) . 2_656 ?
O1 Co1 N1 103.53(6) 2_656 2_656 ?
O2 Co1 O2 96.83(8) 2_656 . ?
O2 Co1 N1 86.32(6) . 2_656 ?
O2 Co1 N1 86.32(6) 2_656 . ?
O2 Co1 N1 77.16(6) 2_656 2_656 ?
O2 Co1 N1 77.16(6) . . ?
N1 Co1 N1 155.08(9) . 2_656 ?
Co1 O1 H1A 120.1 . . ?
Co1 O1 H1B 109.5 . . ?
H1A O1 H1B 101.6 . . ?
C1 O2 Co1 113.91(12) . . ?
C1 O3 C2 114.86(16) . . ?
Co1 N1 H1C 103.3 . . ?
Co1 N1 H1D 118.7 . . ?
H1C N1 H1D 111.0 . . ?
N2 N1 Co1 109.08(11) . . ?
N2 N1 H1C 109.3 . . ?
N2 N1 H1D 105.2 . . ?
N1 N2 H2 120.2 . . ?
C1 N2 N1 115.70(15) . . ?
C1 N2 H2 118.5 . . ?
O2 C1 O3 122.99(17) . . ?
O2 C1 N2 123.94(18) . . ?
O3 C1 N2 113.05(16) . . ?
O3 C2 H2A 109.5 . . ?
O3 C2 H2B 109.5 . . ?
O3 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O4 N3 O5 123.36(18) . . ?
O4 N3 C3 119.12(16) . . ?
O5 N3 C3 117.49(16) . . ?
O6 N4 O7 123.43(17) . . ?
O6 N4 C5 118.37(17) . . ?
O7 N4 C5 118.21(16) . . ?
O8 N5 C7 118.19(16) . . ?
O9 N5 O8 122.72(16) . . ?
O9 N5 C7 119.08(16) . . ?
C4 C3 N3 116.77(16) . . ?
C4 C3 C8 125.89(17) . . ?
C8 C3 N3 117.31(16) . . ?
C3 C4 H4 121.0 . . ?
C3 C4 C5 117.93(17) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 N4 119.47(17) . . ?
C6 C5 N4 119.29(17) . . ?
C6 C5 C4 121.24(17) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 119.91(18) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 N5 115.54(17) . . ?
C6 C7 C8 123.47(17) . . ?
C8 C7 N5 120.99(16) . . ?
O10 C8 C3 122.00(17) . . ?
O10 C8 C7 126.38(17) . . ?
C7 C8 C3 111.54(16) . . ?

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
Co1 O2 C1 O3 -176.57(14) . . . . ?
Co1 O2 C1 N2 5.5(2) . . . . ?
Co1 N1 N2 C1 1.71(19) . . . . ?
N1 N2 C1 O2 -5.0(3) . . . . ?
N1 N2 C1 O3 176.87(15) . . . . ?
C2 O3 C1 O2 3.4(3) . . . . ?
C2 O3 C1 N2 -178.42(18) . . . . ?
O4 N3 C3 C4 -132.77(19) . . . . ?
O4 N3 C3 C8 49.2(2) . . . . ?
O5 N3 C3 C4 45.4(2) . . . . ?
O5 N3 C3 C8 -132.66(18) . . . . ?
O6 N4 C5 C4 7.6(3) . . . . ?
O6 N4 C5 C6 -171.64(18) . . . . ?
O7 N4 C5 C4 -172.50(17) . . . . ?
O7 N4 C5 C6 8.2(3) . . . . ?
O8 N5 C7 C6 -14.1(2) . . . . ?
O8 N5 C7 C8 166.23(17) . . . . ?
O9 N5 C7 C6 164.66(17) . . . . ?
O9 N5 C7 C8 -15.0(3) . . . . ?
N3 C3 C4 C5 -179.71(16) . . . . ?
N3 C3 C8 O10 2.8(3) . . . . ?
N3 C3 C8 C7 179.61(15) . . . . ?
N4 C5 C6 C7 178.62(17) . . . . ?
N5 C7 C8 O10 -4.8(3) . . . . ?
N5 C7 C8 C3 178.52(16) . . . . ?
C3 C4 C5 N4 -178.09(16) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C4 C3 C8 O10 -175.10(18) . . . . ?
C4 C3 C8 C7 1.8(3) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C5 C6 C7 N5 -179.00(16) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C6 C7 C8 O10 175.57(18) . . . . ?
C6 C7 C8 C3 -1.1(3) . . . . ?
C8 C3 C4 C5 -1.8(3) . . . . ?

_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_bwn18209_pl
_database_code_depnum_ccdc_archive 'CCDC 1881676'
loop_
_audit_author_name
_audit_author_address
'Xiaoming Yang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2018-11-27 deposited with the CCDC.	2019-08-06 downloaded from the CCDC.
;
_audit_creation_date             2018-08-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H18 Cd N4 O7, 2(C6 H2 N3 O7), 4(H2 O)'
_chemical_formula_sum            'C16 H30 Cd N10 O25'
_chemical_formula_weight         874.90
_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           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                   12.551(3)
_cell_length_b                   8.5075(17)
_cell_length_c                   30.293(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.02(3)
_cell_angle_gamma                90
_cell_volume                     3194.6(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4864
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4778
_cell_measurement_theta_min      0.6806
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            12527
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         2.723
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega 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                3430
_reflns_number_total             3619
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.064
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3619
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.117
_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)+(0.0255P)²+11.4418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0916
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups, All O(H) groups, All
  O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O11(H11A,H11B), O12(H12), N1(H1), N2(H2A,H2B), O10(H10A,H10B), O13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8)
2.c Idealised Me refined as rotating group:
 C2(H2C,H2D,H2E)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.500000 0.65624(4) 0.250000 0.01686(10) Uani 1 2 d S T P . .
O1 O 0.56132(18) 0.8872(3) 0.29370(7) 0.0217(5) Uani 1 1 d . . . . .
O2 O 0.63755(18) 0.9675(3) 0.36294(7) 0.0236(5) Uani 1 1 d . . . . .
O11 O 0.65041(18) 0.6675(3) 0.21717(7) 0.0280(5) Uani 1 1 d . . . . .
H11A H 0.715862 0.651364 0.227022 0.034 Uiso 1 1 d R . . . .
H11B H 0.652632 0.649414 0.190063 0.034 Uiso 1 1 d R . . . .
O12 O 0.500000 0.3674(4) 0.250000 0.0281(7) Uani 1 2 d S T P . .
H12 H 0.452100 0.308797 0.257540 0.034 Uiso 1 1 d R . . . .
N1 N 0.6187(2) 0.7150(3) 0.34961(8) 0.0212(6) Uani 1 1 d . . . . .
H1 H 0.638098 0.704057 0.377620 0.025 Uiso 1 1 d R . . . .
N2 N 0.5871(2) 0.5848(3) 0.32207(8) 0.0206(5) Uani 1 1 d . . . . .
H2A H 0.641984 0.527763 0.322651 0.025 Uiso 1 1 d R . . . .
H2B H 0.543054 0.522693 0.331031 0.025 Uiso 1 1 d R . . . .
C1 C 0.6020(2) 0.8583(4) 0.33269(9) 0.0168(6) Uani 1 1 d . . . . .
C2 C 0.6080(3) 1.1285(4) 0.35198(11) 0.0275(7) Uani 1 1 d . . . . .
H2C H 0.653340 1.169662 0.331075 0.041 Uiso 1 1 calc GR . . . .
H2D H 0.618588 1.192045 0.379306 0.041 Uiso 1 1 calc GR . . . .
H2E H 0.532083 1.133067 0.338141 0.041 Uiso 1 1 calc GR . . . .
O3 O 0.65173(19) 0.6603(3) 0.44927(7) 0.0248(5) Uani 1 1 d . . . . .
O4 O 0.6422(2) 0.4237(3) 0.42280(7) 0.0321(6) Uani 1 1 d . . . . .
O5 O 0.6554(2) 0.7563(3) 0.60072(8) 0.0300(6) Uani 1 1 d . . . . .
O6 O 0.6045(2) 0.5877(3) 0.64590(8) 0.0325(6) Uani 1 1 d . . . . .
O7 O 0.5169(2) 0.0365(3) 0.57335(8) 0.0279(5) Uani 1 1 d . . . . .
O8 O 0.61606(19) -0.0159(3) 0.52253(7) 0.0254(5) Uani 1 1 d . . . . .
O9 O 0.61372(19) 0.2846(3) 0.62330(7) 0.0240(5) Uani 1 1 d . . . . .
N3 N 0.6442(2) 0.5174(3) 0.45414(8) 0.0205(5) Uani 1 1 d . . . . .
N4 N 0.6288(2) 0.6220(3) 0.60941(8) 0.0197(5) Uani 1 1 d . . . . .
N5 N 0.5786(2) 0.0756(3) 0.54759(8) 0.0191(5) Uani 1 1 d . . . . .
C3 C 0.6352(2) 0.4562(4) 0.49785(9) 0.0178(6) Uani 1 1 d . . . . .
C4 C 0.6393(2) 0.5604(4) 0.53304(10) 0.0175(6) Uani 1 1 d . . . . .
H4 H 0.650045 0.669427 0.528622 0.021 Uiso 1 1 calc R . . . .
C5 C 0.6275(2) 0.5040(4) 0.57466(10) 0.0170(6) Uani 1 1 d . . . . .
C6 C 0.6139(2) 0.3391(4) 0.58504(9) 0.0173(6) Uani 1 1 d . . . . .
C7 C 0.6049(2) 0.2427(4) 0.54484(10) 0.0174(6) Uani 1 1 d . . . . .
C8 C 0.6166(2) 0.2961(4) 0.50330(10) 0.0183(6) Uani 1 1 d . . . . .
H8 H 0.612117 0.225862 0.478701 0.022 Uiso 1 1 calc R . . . .
O10 O 0.31648(19) 0.9980(3) 0.33780(7) 0.0252(5) Uani 1 1 d . . . . .
H10A H 0.341602 0.917685 0.351872 0.030 Uiso 1 1 d R . . . .
H10B H 0.342352 1.063675 0.357272 0.030 Uiso 1 1 d R . . . .
O13 O 0.64453(18) 1.1162(3) 0.24125(7) 0.0250(5) Uani 1 1 d . . . . .
H13A H 0.614258 1.055329 0.257267 0.030 Uiso 1 1 d R . . . .
H13B H 0.651998 1.069739 0.217447 0.030 Uiso 1 1 d R . . . .


_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 O1 2.426(2) 2_655 ?
Cd1 O1 2.426(2) . ?
Cd1 O11 2.270(2) 2_655 ?
Cd1 O11 2.269(2) . ?
Cd1 O12 2.457(3) . ?
Cd1 N2 2.363(3) 2_655 ?
Cd1 N2 2.363(3) . ?
O1 C1 1.236(3) . ?
O2 C1 1.332(4) . ?
O2 C2 1.444(4) . ?
O11 H11A 0.8401 . ?
O11 H11B 0.8402 . ?
O12 H12 0.8400 . ?
O12 H12 0.8399 2_655 ?
N1 H1 0.8504 . ?
N1 N2 1.406(4) . ?
N1 C1 1.326(4) . ?
N2 H2A 0.8399 . ?
N2 H2B 0.8400 . ?
C2 H2C 0.9800 . ?
C2 H2D 0.9800 . ?
C2 H2E 0.9800 . ?
O3 N3 1.230(3) . ?
O4 N3 1.237(3) . ?
O5 N4 1.230(3) . ?
O6 N4 1.227(3) . ?
O7 N5 1.228(3) . ?
O8 N5 1.231(3) . ?
O9 C6 1.248(3) . ?
N3 C3 1.444(4) . ?
N4 C5 1.453(4) . ?
N5 C7 1.465(4) . ?
C3 C4 1.381(4) . ?
C3 C8 1.396(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(4) . ?
C5 C6 1.453(4) . ?
C6 C7 1.458(4) . ?
C7 C8 1.367(4) . ?
C8 H8 0.9500 . ?
O10 H10A 0.8399 . ?
O10 H10B 0.8401 . ?
O13 H13A 0.8400 . ?
O13 H13B 0.8401 . ?

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 Cd1 O1 71.83(10) . 2_655 ?
O1 Cd1 O12 144.08(5) . . ?
O1 Cd1 O12 144.08(5) 2_655 . ?
O11 Cd1 O1 89.45(8) 2_655 2_655 ?
O11 Cd1 O1 86.64(8) . 2_655 ?
O11 Cd1 O1 86.64(8) 2_655 . ?
O11 Cd1 O1 89.45(8) . . ?
O11 Cd1 O11 175.18(13) . 2_655 ?
O11 Cd1 O12 92.41(6) 2_655 . ?
O11 Cd1 O12 92.41(6) . . ?
O11 Cd1 N2 96.86(9) . . ?
O11 Cd1 N2 84.39(9) . 2_655 ?
O11 Cd1 N2 84.39(9) 2_655 . ?
O11 Cd1 N2 96.86(9) 2_655 2_655 ?
N2 Cd1 O1 140.70(8) 2_655 . ?
N2 Cd1 O1 140.70(8) . 2_655 ?
N2 Cd1 O1 69.09(8) 2_655 2_655 ?
N2 Cd1 O1 69.09(8) . . ?
N2 Cd1 O12 75.09(6) . . ?
N2 Cd1 O12 75.09(6) 2_655 . ?
N2 Cd1 N2 150.17(13) 2_655 . ?
C1 O1 Cd1 114.1(2) . . ?
C1 O2 C2 117.2(2) . . ?
Cd1 O11 H11A 132.2 . . ?
Cd1 O11 H11B 125.3 . . ?
H11A O11 H11B 97.9 . . ?
Cd1 O12 H12 126.4 . . ?
Cd1 O12 H12 126.439(9) . 2_655 ?
H12 O12 H12 107.1 . 2_655 ?
N2 N1 H1 121.0 . . ?
C1 N1 H1 119.3 . . ?
C1 N1 N2 118.8(2) . . ?
Cd1 N2 H2A 115.3 . . ?
Cd1 N2 H2B 103.1 . . ?
N1 N2 Cd1 113.07(18) . . ?
N1 N2 H2A 106.8 . . ?
N1 N2 H2B 116.2 . . ?
H2A N2 H2B 102.1 . . ?
O1 C1 O2 124.2(3) . . ?
O1 C1 N1 124.6(3) . . ?
N1 C1 O2 111.1(3) . . ?
O2 C2 H2C 109.5 . . ?
O2 C2 H2D 109.5 . . ?
O2 C2 H2E 109.5 . . ?
H2C C2 H2D 109.5 . . ?
H2C C2 H2E 109.5 . . ?
H2D C2 H2E 109.5 . . ?
O3 N3 O4 122.5(3) . . ?
O3 N3 C3 119.0(3) . . ?
O4 N3 C3 118.4(3) . . ?
O5 N4 C5 117.3(2) . . ?
O6 N4 O5 121.9(3) . . ?
O6 N4 C5 120.8(3) . . ?
O7 N5 O8 124.1(3) . . ?
O7 N5 C7 118.0(3) . . ?
O8 N5 C7 117.8(2) . . ?
C4 C3 N3 118.5(3) . . ?
C4 C3 C8 121.4(3) . . ?
C8 C3 N3 119.9(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 N4 115.6(3) . . ?
C4 C5 C6 124.6(3) . . ?
C6 C5 N4 119.9(3) . . ?
O9 C6 C5 125.2(3) . . ?
O9 C6 C7 123.8(3) . . ?
C5 C6 C7 111.0(2) . . ?
C6 C7 N5 119.1(2) . . ?
C8 C7 N5 115.6(3) . . ?
C8 C7 C6 125.2(3) . . ?
C3 C8 H8 120.7 . . ?
C7 C8 C3 118.5(3) . . ?
C7 C8 H8 120.7 . . ?
H10A O10 H10B 96.4 . . ?
H13A O13 H13B 109.1 . . ?

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
Cd1 O1 C1 O2 -177.6(2) . . . . ?
Cd1 O1 C1 N1 4.3(4) . . . . ?
N2 N1 C1 O1 -1.0(5) . . . . ?
N2 N1 C1 O2 -179.3(2) . . . . ?
C1 N1 N2 Cd1 -3.0(3) . . . . ?
C2 O2 C1 O1 12.3(4) . . . . ?
C2 O2 C1 N1 -169.3(3) . . . . ?
O3 N3 C3 C4 -2.3(4) . . . . ?
O3 N3 C3 C8 174.1(3) . . . . ?
O4 N3 C3 C4 178.9(3) . . . . ?
O4 N3 C3 C8 -4.7(4) . . . . ?
O5 N4 C5 C4 -10.2(4) . . . . ?
O5 N4 C5 C6 170.1(3) . . . . ?
O6 N4 C5 C4 170.0(3) . . . . ?
O6 N4 C5 C6 -9.7(4) . . . . ?
O7 N5 C7 C6 34.8(4) . . . . ?
O7 N5 C7 C8 -143.6(3) . . . . ?
O8 N5 C7 C6 -148.2(3) . . . . ?
O8 N5 C7 C8 33.4(4) . . . . ?
O9 C6 C7 N5 9.3(4) . . . . ?
O9 C6 C7 C8 -172.5(3) . . . . ?
N3 C3 C4 C5 178.0(3) . . . . ?
N3 C3 C8 C7 -177.8(3) . . . . ?
N4 C5 C6 O9 -7.7(5) . . . . ?
N4 C5 C6 C7 174.7(2) . . . . ?
N5 C7 C8 C3 176.2(3) . . . . ?
C3 C4 C5 N4 -177.8(3) . . . . ?
C3 C4 C5 C6 1.9(5) . . . . ?
C4 C3 C8 C7 -1.6(4) . . . . ?
C4 C5 C6 O9 172.6(3) . . . . ?
C4 C5 C6 C7 -4.9(4) . . . . ?
C5 C6 C7 N5 -173.2(2) . . . . ?
C5 C6 C7 C8 5.1(4) . . . . ?
C6 C7 C8 C3 -2.2(5) . . . . ?
C8 C3 C4 C5 1.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
