# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_xhh-21203
_database_code_depnum_ccdc_archive 'CCDC 2157089'
loop_
_audit_author_name
_audit_author_address
'Haohui Xie'
;FAFU
China
;
_audit_update_record             
;
2022-10-31 deposited with the CCDC.	2022-12-14 downloaded from the CCDC.
;
_audit_creation_date             2022-03-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H10 Co N16, H2 O'
_chemical_formula_sum            'C8 H12 Co N16 O'
_chemical_formula_weight         407.27
_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'
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.3406(4)
_cell_length_b                   15.4425(7)
_cell_length_c                   14.6670(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.687(6)
_cell_angle_gamma                90
_cell_volume                     1622.02(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6849
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      28.8880
_cell_measurement_theta_min      1.9330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.64a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.26
_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  0.0375
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.804
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10729
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.245
_diffrn_reflns_theta_min         1.940
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.804
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  30.00   0.50    0.61    --  -11.30 -99.00-150.00   60
  2  ω    -11.00  14.00   0.50    0.61    --  -11.30 -99.00-180.00   50
  3  ω     -8.00  22.00   0.50    0.61    --  -11.30 -99.00-120.00   60
  4  ω     -6.00  29.00   0.50    0.61    --  -11.30 -99.00  30.00   70
  5  ω    -59.00  34.00   0.50    0.61    --   10.52 -58.00   3.00  186
  6  ω     19.00  84.00   0.50    0.61    --   10.52  58.00 144.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0416696000
_diffrn_orient_matrix_UB_12      -0.0085063000
_diffrn_orient_matrix_UB_13      0.0473744000
_diffrn_orient_matrix_UB_21      0.0610120000
_diffrn_orient_matrix_UB_22      -0.0303550000
_diffrn_orient_matrix_UB_23      -0.0141939000
_diffrn_orient_matrix_UB_31      0.0659997000
_diffrn_orient_matrix_UB_32      0.0334540000
_diffrn_orient_matrix_UB_33      -0.0008635000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3095
_reflns_number_total             3544
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3544
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.068
_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)+(0.0472P)²+1.7697P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1036
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H22A-H22B \\sim H22B-H22C
 with sigma of 0.02
 H24A-H24B \\sim H24B-H24C
 with sigma of 0.02
3.a X=CH2 refined with riding coordinates:
 N30(H30A,H30B), N25(H25A,H25B)
3.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_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 0.57375(4) 0.48802(2) 0.22638(2) 0.01138(11) Uani 1 1 d . . . . .
N14 N 0.7442(3) 0.51823(13) 0.13075(15) 0.0146(4) Uani 1 1 d . . . . .
N24 N 0.5018(3) 0.75004(12) 0.30365(14) 0.0149(4) Uani 1 1 d . . . . .
N26 N 0.5544(3) 0.35509(12) 0.18361(14) 0.0135(4) Uani 1 1 d . . . . .
N16 N 1.3270(3) 0.50680(13) 0.11839(15) 0.0154(4) Uani 1 1 d . . . . .
N12 N 0.1491(3) 0.46367(14) 0.40727(15) 0.0170(4) Uani 1 1 d . . . . .
N11 N -0.1848(3) 0.47235(13) 0.33107(15) 0.0175(4) Uani 1 1 d . . . . .
N13 N 0.4007(3) 0.46283(13) 0.32064(15) 0.0167(4) Uani 1 1 d . . . . .
N29 N 0.4788(3) 0.23989(13) 0.09897(14) 0.0158(4) Uani 1 1 d . . . . .
N30 N 0.5570(3) 0.36467(13) 0.02142(15) 0.0189(5) Uani 1 1 d . . . . .
H30A H 0.594801 0.418891 0.025604 0.023 Uiso 1 1 calc R U . . .
H30B H 0.536856 0.337767 -0.032761 0.023 Uiso 1 1 calc R U . . .
N28 N 0.4712(3) 0.21933(13) 0.18873(15) 0.0203(5) Uani 1 1 d . . . . .
N15 N 1.0191(3) 0.57819(13) 0.08153(15) 0.0171(4) Uani 1 1 d . . . . .
N27 N 0.5166(3) 0.28805(13) 0.23789(15) 0.0178(4) Uani 1 1 d . . . . .
N21 N 0.5612(3) 0.62396(12) 0.25241(14) 0.0143(4) Uani 1 1 d . . . . .
N23 N 0.4816(3) 0.75716(13) 0.20967(15) 0.0184(4) Uani 1 1 d . . . . .
N22 N 0.5182(3) 0.68202(13) 0.18065(15) 0.0171(4) Uani 1 1 d . . . . .
N25 N 0.5874(3) 0.63808(14) 0.41648(15) 0.0216(5) Uani 1 1 d . . . . .
H25A H 0.622310 0.583889 0.427666 0.026 Uiso 1 1 calc R U . . .
H25B H 0.576641 0.672377 0.462924 0.026 Uiso 1 1 calc R U . . .
C13 C 0.8770(3) 0.54415(14) 0.10962(16) 0.0127(5) Uani 1 1 d . . . . .
C21 C 0.5509(3) 0.66817(15) 0.32934(17) 0.0141(5) Uani 1 1 d . . . . .
C12 C 0.2771(3) 0.46346(14) 0.35746(16) 0.0130(5) Uani 1 1 d . . . . .
C23 C 0.5301(3) 0.32328(15) 0.09719(17) 0.0138(5) Uani 1 1 d . . . . .
C14 C 1.1797(3) 0.53748(14) 0.10287(16) 0.0125(5) Uani 1 1 d . . . . .
C11 C -0.0267(3) 0.46798(15) 0.36274(16) 0.0140(5) Uani 1 1 d . . . . .
C22 C 0.4640(4) 0.82330(16) 0.35989(18) 0.0206(5) Uani 1 1 d . . . . .
H22A H 0.582350 0.848552 0.393373 0.031 Uiso 1 1 calc DR U . . .
H22B H 0.392628 0.803322 0.405020 0.031 Uiso 1 1 calc DR U . . .
H22C H 0.391718 0.867142 0.318955 0.031 Uiso 1 1 calc DR U . . .
C24 C 0.4323(4) 0.17861(16) 0.02162(19) 0.0227(6) Uani 1 1 d . . . . .
H24A H 0.415045 0.120823 0.046051 0.034 Uiso 1 1 calc DR U . . .
H24B H 0.533842 0.176950 -0.011945 0.034 Uiso 1 1 calc DR U . . .
H24C H 0.316604 0.196879 -0.021185 0.034 Uiso 1 1 calc DR U . . .
O1W O 0.5161(3) 0.73252(14) 0.56860(14) 0.0265(5) Uani 1 1 d . . . . .
H1WA H 0.531(5) 0.778(3) 0.574(3) 0.039(11) Uiso 1 1 d . . . . .
H1WB H 0.517(5) 0.714(2) 0.621(3) 0.042(11) Uiso 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 N14 2.126(2) . ?
Co1 N26 2.142(2) . ?
Co1 N16 2.148(2) 1_455 ?
Co1 N11 2.088(2) 1_655 ?
Co1 N13 2.109(2) . ?
Co1 N21 2.139(2) . ?
N14 C13 1.157(3) . ?
N24 N23 1.358(3) . ?
N24 C21 1.346(3) . ?
N24 C22 1.462(3) . ?
N26 N27 1.371(3) . ?
N26 C23 1.334(3) . ?
N16 C14 1.156(3) . ?
N12 C12 1.311(3) . ?
N12 C11 1.314(3) . ?
N11 C11 1.154(3) . ?
N13 C12 1.153(3) . ?
N29 N28 1.367(3) . ?
N29 C23 1.344(3) . ?
N29 C24 1.459(3) . ?
N30 H30A 0.8800 . ?
N30 H30B 0.8800 . ?
N30 C23 1.334(3) . ?
N28 N27 1.285(3) . ?
N15 C13 1.313(3) . ?
N15 C14 1.311(3) . ?
N21 N22 1.366(3) . ?
N21 C21 1.335(3) . ?
N23 N22 1.285(3) . ?
N25 H25A 0.8800 . ?
N25 H25B 0.8800 . ?
N25 C21 1.331(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O1W H1WA 0.72(4) . ?
O1W H1WB 0.82(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N14 Co1 N26 91.59(7) . . ?
N14 Co1 N16 90.41(8) . 1_455 ?
N14 Co1 N21 87.54(7) . . ?
N26 Co1 N16 85.56(8) . 1_455 ?
N11 Co1 N14 89.04(8) 1_655 . ?
N11 Co1 N26 95.46(8) 1_655 . ?
N11 Co1 N16 178.85(8) 1_655 1_455 ?
N11 Co1 N13 91.87(8) 1_655 . ?
N11 Co1 N21 92.60(8) 1_655 . ?
N13 Co1 N14 177.85(8) . . ?
N13 Co1 N26 90.27(8) . . ?
N13 Co1 N16 88.65(8) . 1_455 ?
N13 Co1 N21 90.47(8) . . ?
N21 Co1 N26 171.88(8) . . ?
N21 Co1 N16 86.37(8) . 1_455 ?
C13 N14 Co1 154.8(2) . . ?
N23 N24 C22 121.19(19) . . ?
C21 N24 N23 108.86(19) . . ?
C21 N24 C22 129.9(2) . . ?
N27 N26 Co1 124.22(15) . . ?
C23 N26 Co1 128.13(16) . . ?
C23 N26 N27 105.76(19) . . ?
C14 N16 Co1 143.23(19) . 1_655 ?
C12 N12 C11 118.0(2) . . ?
C11 N11 Co1 156.8(2) . 1_455 ?
C12 N13 Co1 162.6(2) . . ?
N28 N29 C24 123.1(2) . . ?
C23 N29 N28 108.2(2) . . ?
C23 N29 C24 128.7(2) . . ?
H30A N30 H30B 120.0 . . ?
C23 N30 H30A 120.0 . . ?
C23 N30 H30B 120.0 . . ?
N27 N28 N29 106.72(19) . . ?
C14 N15 C13 117.9(2) . . ?
N28 N27 N26 111.01(19) . . ?
N22 N21 Co1 121.22(15) . . ?
C21 N21 Co1 131.70(16) . . ?
C21 N21 N22 105.62(19) . . ?
N22 N23 N24 106.19(19) . . ?
N23 N22 N21 111.56(19) . . ?
H25A N25 H25B 120.0 . . ?
C21 N25 H25A 120.0 . . ?
C21 N25 H25B 120.0 . . ?
N14 C13 N15 175.4(3) . . ?
N21 C21 N24 107.8(2) . . ?
N25 C21 N24 125.6(2) . . ?
N25 C21 N21 126.6(2) . . ?
N13 C12 N12 174.3(3) . . ?
N26 C23 N29 108.3(2) . . ?
N30 C23 N26 127.0(2) . . ?
N30 C23 N29 124.7(2) . . ?
N16 C14 N15 174.7(2) . . ?
N11 C11 N12 174.1(3) . . ?
N24 C22 H22A 109.5 . . ?
N24 C22 H22B 109.5 . . ?
N24 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N29 C24 H24A 109.5 . . ?
N29 C24 H24B 109.5 . . ?
N29 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
H1WA O1W H1WB 106(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
Co1 N26 N27 N28 165.20(16) . . . . ?
Co1 N26 C23 N29 -164.53(16) . . . . ?
Co1 N26 C23 N30 17.5(4) . . . . ?
Co1 N21 N22 N23 167.15(16) . . . . ?
Co1 N21 C21 N24 -165.52(17) . . . . ?
Co1 N21 C21 N25 16.2(4) . . . . ?
N24 N23 N22 N21 0.5(3) . . . . ?
N29 N28 N27 N26 0.2(3) . . . . ?
N28 N29 C23 N26 0.0(3) . . . . ?
N28 N29 C23 N30 178.0(2) . . . . ?
N27 N26 C23 N29 0.2(3) . . . . ?
N27 N26 C23 N30 -177.8(2) . . . . ?
N23 N24 C21 N21 -0.1(3) . . . . ?
N23 N24 C21 N25 178.2(2) . . . . ?
N22 N21 C21 N24 0.4(3) . . . . ?
N22 N21 C21 N25 -177.8(2) . . . . ?
C21 N24 N23 N22 -0.2(3) . . . . ?
C21 N21 N22 N23 -0.6(3) . . . . ?
C23 N26 N27 N28 -0.2(3) . . . . ?
C23 N29 N28 N27 -0.1(3) . . . . ?
C22 N24 N23 N22 -177.8(2) . . . . ?
C22 N24 C21 N21 177.1(2) . . . . ?
C22 N24 C21 N25 -4.6(4) . . . . ?
C24 N29 N28 N27 -178.7(2) . . . . ?
C24 N29 C23 N26 178.4(2) . . . . ?
C24 N29 C23 N30 -3.6(4) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.460
_oxdiff_exptl_absorpt_empirical_full_min 0.361
####################################################################### 
# 
# 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_xxh-89
_database_code_depnum_ccdc_archive 'CCDC 2157091'
loop_
_audit_author_name
_audit_author_address
'Haohui Xie'
;FAFU
China
;
_audit_update_record             
;
2022-10-31 deposited with the CCDC.	2022-12-14 downloaded from the CCDC.
;
_audit_creation_date             2022-03-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H10 Cd N16'
_chemical_formula_sum            'C8 H10 Cd N16'
_chemical_formula_weight         442.72
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.9693(2)
_cell_length_b                   8.9384(3)
_cell_length_c                   13.1610(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.171(3)
_cell_angle_gamma                90
_cell_volume                     806.97(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3739
_cell_measurement_temperature    296.03(10)
_cell_measurement_theta_max      29.1330
_cell_measurement_theta_min      2.7500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.386
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.64a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.822
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       bolck
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.804
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5827
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.416
_diffrn_reflns_theta_min         2.769
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.03(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.804
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00 -14.00   0.50    0.05    --  -11.30 112.00  47.00   52
  2  ω    -16.00  48.00   0.50    0.05    --   10.52  57.00 150.00  128
  3  ω     61.00  86.00   0.50    0.05    --   10.52  57.00 150.00   50
  4  ω    -38.00  58.00   0.50    0.05    --  -11.30  57.00 150.00  192
  5  ω      8.00  47.00   0.50    0.05    --   10.52-112.00 -45.00   78
  6  ω      2.00  32.00   0.50    0.05    --  -11.30 -99.00 -90.00   60
  7  ω      1.00  28.00   0.50    0.05    --  -11.30 -99.00-150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0193079000
_diffrn_orient_matrix_UB_12      0.0778291000
_diffrn_orient_matrix_UB_13      -0.0047909000
_diffrn_orient_matrix_UB_21      0.0378156000
_diffrn_orient_matrix_UB_22      0.0013209000
_diffrn_orient_matrix_UB_23      -0.0466130000
_diffrn_orient_matrix_UB_31      -0.0942932000
_diffrn_orient_matrix_UB_32      -0.0153717000
_diffrn_orient_matrix_UB_33      -0.0283321000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1461
_reflns_number_total             1793
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL n/a (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0238(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1793
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0220
_refine_ls_restrained_S_all      1.096
_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)+(0.0319P)²+0.0075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0578
_refine_ls_wR_factor_ref         0.0615
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a X=CH2 refined with riding coordinates:
 N25(H25a,H25b)
2.b Idealised Me refined as rotating group:
 C22(H22a,H22b,H22c)
;
_atom_sites_solution_hydrogens   geom
_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
Cd1 Cd 1.000000 0.500000 0.500000 0.02739(12) Uani 1 2 d S . P . .
N24 N 0.4930(2) 0.21755(18) 0.36401(13) 0.0343(4) Uani 1 1 d . . . . .
N21 N 0.7397(2) 0.36155(19) 0.41190(12) 0.0336(4) Uani 1 1 d . . . . .
N13 N 0.8727(3) 0.7293(2) 0.43058(14) 0.0419(4) Uani 1 1 d . . . . .
N22 N 0.7196(3) 0.3332(2) 0.30909(13) 0.0452(5) Uani 1 1 d . . . . .
N11 N 0.8495(4) 0.98616(19) 0.14574(19) 0.0414(5) Uani 1 1 d . . . . .
N23 N 0.5725(3) 0.2480(2) 0.27885(15) 0.0471(5) Uani 1 1 d . . . . .
N25 N 0.5645(3) 0.2771(2) 0.54100(15) 0.0553(6) Uani 1 1 d . . . . .
H25A H 0.640741 0.321720 0.590225 0.066 Uiso 1 1 calc R U . . .
H25B H 0.467314 0.225825 0.554082 0.066 Uiso 1 1 calc R U . . .
C12 C 0.8812(3) 0.8333(2) 0.38043(16) 0.0341(5) Uani 1 1 d . . . . .
C21 C 0.5971(3) 0.2873(2) 0.44419(16) 0.0334(5) Uani 1 1 d . . . . .
C11 C 0.8678(3) 0.9673(3) 0.2332(2) 0.0358(5) Uani 1 1 d . . . . .
C22 C 0.3245(3) 0.1189(3) 0.35954(19) 0.0487(6) Uani 1 1 d . . . . .
H22A H 0.217028 0.174566 0.376989 0.073 Uiso 1 1 calc R U . . .
H22B H 0.356829 0.038268 0.407669 0.073 Uiso 1 1 calc R U . . .
H22C H 0.288942 0.079211 0.291034 0.073 Uiso 1 1 calc R U . . .
N12 N 0.8894(4) 0.9592(3) 0.33255(17) 0.0536(6) 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
Cd1 N21 2.3288(16) 3_766 ?
Cd1 N21 2.3288(16) . ?
Cd1 N13 2.3527(18) 3_766 ?
Cd1 N13 2.3527(18) . ?
Cd1 N11 2.346(2) 4_576 ?
Cd1 N11 2.346(2) 2_745 ?
N24 N23 1.363(2) . ?
N24 C21 1.326(3) . ?
N24 C22 1.461(2) . ?
N21 N22 1.359(2) . ?
N21 C21 1.326(3) . ?
N13 C12 1.148(3) . ?
N22 N23 1.283(3) . ?
N11 C11 1.148(4) . ?
N25 H25A 0.8600 . ?
N25 H25B 0.8600 . ?
N25 C21 1.336(3) . ?
C12 N12 1.296(3) . ?
C11 N12 1.291(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
N21 Cd1 N21 180.0 3_766 . ?
N21 Cd1 N13 86.42(6) 3_766 . ?
N21 Cd1 N13 93.58(6) 3_766 3_766 ?
N21 Cd1 N13 86.42(6) . 3_766 ?
N21 Cd1 N13 93.58(6) . . ?
N21 Cd1 N11 89.22(7) 3_766 4_576 ?
N21 Cd1 N11 90.78(7) . 4_576 ?
N21 Cd1 N11 90.78(7) 3_766 2_745 ?
N21 Cd1 N11 89.22(7) . 2_745 ?
N13 Cd1 N13 180.0 . 3_766 ?
N11 Cd1 N13 94.54(7) 2_745 3_766 ?
N11 Cd1 N13 85.46(7) 2_745 . ?
N11 Cd1 N13 94.54(7) 4_576 . ?
N11 Cd1 N13 85.46(7) 4_576 3_766 ?
N11 Cd1 N11 180.0 4_576 2_745 ?
N23 N24 C22 121.87(18) . . ?
C21 N24 N23 108.40(16) . . ?
C21 N24 C22 129.70(18) . . ?
N22 N21 Cd1 121.95(12) . . ?
C21 N21 Cd1 131.94(13) . . ?
C21 N21 N22 105.93(16) . . ?
C12 N13 Cd1 151.02(16) . . ?
N23 N22 N21 110.84(16) . . ?
C11 N11 Cd1 147.2(2) . 2_755 ?
N22 N23 N24 106.40(17) . . ?
H25A N25 H25B 120.0 . . ?
C21 N25 H25A 120.0 . . ?
C21 N25 H25B 120.0 . . ?
N13 C12 N12 173.8(2) . . ?
N24 C21 N25 124.40(19) . . ?
N21 C21 N24 108.43(17) . . ?
N21 C21 N25 127.11(19) . . ?
N11 C11 N12 174.7(3) . . ?
N24 C22 H22A 109.5 . . ?
N24 C22 H22B 109.5 . . ?
N24 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 N12 C12 122.2(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
Cd1 N21 N22 N23 176.23(15) . . . . ?
Cd1 N21 C21 N24 -175.48(13) . . . . ?
Cd1 N21 C21 N25 1.9(3) . . . . ?
N21 N22 N23 N24 -0.5(3) . . . . ?
N22 N21 C21 N24 -0.6(2) . . . . ?
N22 N21 C21 N25 176.9(2) . . . . ?
N23 N24 C21 N21 0.3(2) . . . . ?
N23 N24 C21 N25 -177.2(2) . . . . ?
C21 N24 N23 N22 0.2(2) . . . . ?
C21 N21 N22 N23 0.7(3) . . . . ?
C22 N24 N23 N22 -178.10(19) . . . . ?
C22 N24 C21 N21 178.3(2) . . . . ?
C22 N24 C21 N25 0.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.299
_oxdiff_exptl_absorpt_empirical_full_min 0.796
####################################################################### 
# 
# 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_xhh-248131
_database_code_depnum_ccdc_archive 'CCDC 2167317'
loop_
_audit_author_name
_audit_author_address
'Haohui Xie'
;FAFU
China
;
_audit_update_record             
;
2022-10-31 deposited with the CCDC.	2022-12-14 downloaded from the CCDC.
;
_audit_creation_date             2022-03-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C4 H5 Cd0.5 N8)'
_chemical_formula_sum            'C8 H10 Cd N16'
_chemical_formula_weight         442.72
_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'

_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                   7.5280(6)
_cell_length_b                   8.7978(11)
_cell_length_c                   13.4483(9)
_cell_angle_alpha                93.655(7)
_cell_angle_beta                 93.742(6)
_cell_angle_gamma                110.729(9)
_cell_volume                     827.64(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5402
_cell_measurement_temperature    298.21(10)
_cell_measurement_theta_max      28.4830
_cell_measurement_theta_min      2.4710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.351
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.64a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       slice
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.805
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10419
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.805
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.388
_diffrn_reflns_theta_min         1.524
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.21(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.805
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  42.00   0.50    0.05    --   10.52 -77.00-120.00  208
  2  ω     24.00  57.00   0.50    0.05    --   10.52-138.00-116.00   66
  3  ω     23.00  50.00   0.50    0.05    --   10.52-131.00  59.00   54
  4  ω    -28.00  51.00   0.50    0.05    --  -11.30  19.00-180.00  158
  5  ω    -25.00  25.00   0.50    0.05    --  -11.30  19.00 -30.00  100
  6  ω     35.00  60.00   0.50    0.05    --  -11.30  19.00 -30.00   50
  7  ω    -44.00  57.00   0.50    0.05    --  -11.30  77.00  30.00  202
  8  ω    -72.00 -47.00   0.50    0.05    --  -11.30 138.00 -54.00   50
  9  ω    -74.00 -49.00   0.50    0.05    --  -11.30 131.00 130.00   50
 10  ω    -10.00  34.00   0.50    0.05    --  -11.30 -99.00-150.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0226081000
_diffrn_orient_matrix_UB_12      0.0709305000
_diffrn_orient_matrix_UB_13      -0.0054541000
_diffrn_orient_matrix_UB_21      0.0089313000
_diffrn_orient_matrix_UB_22      0.0162317000
_diffrn_orient_matrix_UB_23      0.0527954000
_diffrn_orient_matrix_UB_31      0.0982290000
_diffrn_orient_matrix_UB_32      0.0469205000
_diffrn_orient_matrix_UB_33      -0.0009073000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2855
_reflns_number_total             3676
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0300(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3676
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0269
_refine_ls_restrained_S_all      1.041
_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)+(0.0343P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0716
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N15(H15a,H15b), N25(H25a,H25b)
2.b Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C11(H11a,H11b,H11c)
;
_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
Cd2 Cd 0.500000 1.000000 0.000000 0.03531(10) Uani 1 2 d S . P . .
Cd1 Cd 0.500000 0.000000 0.500000 0.04070(11) Uani 1 2 d S . P . .
N21 N 0.3713(2) 0.7163(2) 0.01111(14) 0.0422(5) Uani 1 1 d . . . . .
N23 N 0.2129(3) 0.4707(3) -0.03899(17) 0.0524(6) Uani 1 1 d . . . . .
N11 N 0.4705(3) 0.2222(3) 0.41946(14) 0.0490(5) Uani 1 1 d . . . . .
N14 N 0.4620(3) 0.4093(3) 0.31871(15) 0.0481(5) Uani 1 1 d . . . . .
N22 N 0.2693(3) 0.6173(3) -0.06853(15) 0.0497(5) Uani 1 1 d . . . . .
N24 N 0.2707(3) 0.4629(3) 0.05585(16) 0.0558(6) Uani 1 1 d . . . . .
N43 N -0.2450(3) 1.0303(3) 0.11596(16) 0.0549(6) Uani 1 1 d . . . . .
N15 N 0.6977(3) 0.2895(3) 0.29867(16) 0.0579(6) Uani 1 1 d . . . . .
H15A H 0.696248 0.192237 0.304299 0.070 Uiso 1 1 d R U . . .
H15B H 0.687358 0.304557 0.236289 0.070 Uiso 1 1 d R U . . .
N42 N 0.0786(3) 1.1196(3) 0.19708(16) 0.0588(7) Uani 1 1 d . . . . .
N13 N 0.3306(3) 0.3823(3) 0.38429(15) 0.0512(5) Uani 1 1 d . . . . .
N12 N 0.3309(3) 0.2730(3) 0.44420(16) 0.0594(6) Uani 1 1 d . . . . .
N41 N 0.3304(3) 1.0422(4) 0.12952(19) 0.0579(7) Uani 1 1 d . . . . .
C42 C -0.0905(3) 1.0710(3) 0.15015(17) 0.0397(6) Uani 1 1 d . . . . .
N32 N 1.1145(3) 0.2021(4) 0.65803(17) 0.0651(8) Uani 1 1 d . . . . .
N33 N 1.3321(4) 0.0591(4) 0.62797(18) 0.0597(7) Uani 1 1 d . . . . .
C41 C 0.2088(3) 1.0762(4) 0.15768(18) 0.0448(7) Uani 1 1 d . . . . .
N31 N 0.7976(3) 0.1523(4) 0.5803(2) 0.0747(8) Uani 1 1 d . . . . .
C22 C 0.3694(3) 0.6185(3) 0.08443(18) 0.0461(6) Uani 1 1 d . . . . .
C12 C 0.5478(4) 0.3073(4) 0.34267(18) 0.0424(6) Uani 1 1 d . . . . .
C31 C 0.9460(4) 0.1671(4) 0.61392(19) 0.0470(6) Uani 1 1 d . . . . .
C32 C 1.2224(4) 0.1209(4) 0.63725(18) 0.0486(7) Uani 1 1 d . . . . .
N25 N 0.4540(5) 0.6771(4) 0.17819(19) 0.0808(9) Uani 1 1 d . . . . .
H25A H 0.484374 0.600959 0.203707 0.097 Uiso 1 1 d R U . . .
H25B H 0.557021 0.761118 0.176396 0.097 Uiso 1 1 d R U . . .
C21 C 0.0955(4) 0.3274(4) -0.1034(3) 0.0799(10) Uani 1 1 d . . . . .
H21A H 0.036952 0.359976 -0.159658 0.120 Uiso 1 1 calc R U . . .
H21B H -0.001723 0.258068 -0.066685 0.120 Uiso 1 1 calc R U . . .
H21C H 0.173353 0.269044 -0.126747 0.120 Uiso 1 1 calc R U . . .
C11 C 0.1937(5) 0.4636(5) 0.3857(3) 0.0775(10) Uani 1 1 d . . . . .
H11A H 0.259991 0.579688 0.391752 0.116 Uiso 1 1 calc R U . . .
H11B H 0.119492 0.433661 0.441535 0.116 Uiso 1 1 calc R U . . .
H11C H 0.110790 0.431448 0.324643 0.116 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd2 N21 2.355(2) . ?
Cd2 N21 2.355(2) 2_675 ?
Cd2 N43 2.320(2) 1_655 ?
Cd2 N43 2.320(2) 2_575 ?
Cd2 N41 2.312(2) . ?
Cd2 N41 2.312(2) 2_675 ?
Cd1 N11 2.365(2) 2_656 ?
Cd1 N11 2.365(2) . ?
Cd1 N33 2.338(2) 1_455 ?
Cd1 N33 2.338(2) 2_756 ?
Cd1 N31 2.314(2) 2_656 ?
Cd1 N31 2.314(2) . ?
N21 N22 1.340(3) . ?
N21 C22 1.347(3) . ?
N23 N22 1.304(3) . ?
N23 N24 1.334(3) . ?
N23 C21 1.447(4) . ?
N11 N12 1.332(3) . ?
N11 C12 1.354(3) . ?
N14 N13 1.337(3) . ?
N14 C12 1.321(4) . ?
N24 C22 1.323(3) . ?
N43 C42 1.143(3) . ?
N15 H15A 0.8603 . ?
N15 H15B 0.8604 . ?
N15 C12 1.360(3) . ?
N42 C42 1.295(3) . ?
N42 C41 1.302(3) . ?
N13 N12 1.294(3) . ?
N13 C11 1.448(3) . ?
N41 C41 1.138(4) . ?
N32 C31 1.288(3) . ?
N32 C32 1.290(4) . ?
N33 C32 1.147(4) . ?
N31 C31 1.137(3) . ?
C22 N25 1.357(3) . ?
N25 H25A 0.8638 . ?
N25 H25B 0.8648 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
N21 Cd2 N21 180.00(9) 2_675 . ?
N43 Cd2 N21 91.89(8) 2_575 2_675 ?
N43 Cd2 N21 88.11(8) 1_655 2_675 ?
N43 Cd2 N21 88.11(8) 2_575 . ?
N43 Cd2 N21 91.89(8) 1_655 . ?
N43 Cd2 N43 180.0 2_575 1_655 ?
N41 Cd2 N21 90.35(9) . . ?
N41 Cd2 N21 90.35(9) 2_675 2_675 ?
N41 Cd2 N21 89.65(9) . 2_675 ?
N41 Cd2 N21 89.65(9) 2_675 . ?
N41 Cd2 N43 90.83(8) . 2_575 ?
N41 Cd2 N43 89.17(8) . 1_655 ?
N41 Cd2 N43 90.83(8) 2_675 1_655 ?
N41 Cd2 N43 89.17(8) 2_675 2_575 ?
N41 Cd2 N41 180.0 2_675 . ?
N11 Cd1 N11 180.0 . 2_656 ?
N33 Cd1 N11 88.90(9) 2_756 2_656 ?
N33 Cd1 N11 91.10(9) 2_756 . ?
N33 Cd1 N11 88.90(9) 1_455 . ?
N33 Cd1 N11 91.10(9) 1_455 2_656 ?
N33 Cd1 N33 180.0 2_756 1_455 ?
N31 Cd1 N11 86.24(9) 2_656 . ?
N31 Cd1 N11 86.23(9) . 2_656 ?
N31 Cd1 N11 93.77(9) . . ?
N31 Cd1 N11 93.76(9) 2_656 2_656 ?
N31 Cd1 N33 85.39(9) 2_656 1_455 ?
N31 Cd1 N33 85.39(10) . 2_756 ?
N31 Cd1 N33 94.61(9) . 1_455 ?
N31 Cd1 N33 94.61(9) 2_656 2_756 ?
N31 Cd1 N31 180.0 2_656 . ?
N22 N21 Cd2 119.60(15) . . ?
N22 N21 C22 105.7(2) . . ?
C22 N21 Cd2 134.64(16) . . ?
N22 N23 N24 114.8(2) . . ?
N22 N23 C21 122.8(3) . . ?
N24 N23 C21 122.4(3) . . ?
N12 N11 Cd1 116.97(15) . . ?
N12 N11 C12 106.2(2) . . ?
C12 N11 Cd1 136.32(18) . . ?
C12 N14 N13 101.8(2) . . ?
N23 N22 N21 105.5(2) . . ?
C22 N24 N23 101.2(2) . . ?
C42 N43 Cd2 158.8(2) . 1_455 ?
H15A N15 H15B 109.4 . . ?
C12 N15 H15A 109.0 . . ?
C12 N15 H15B 109.3 . . ?
C42 N42 C41 118.6(2) . . ?
N14 N13 C11 122.8(2) . . ?
N12 N13 N14 114.5(2) . . ?
N12 N13 C11 122.6(2) . . ?
N13 N12 N11 105.8(2) . . ?
C41 N41 Cd2 150.4(2) . . ?
N43 C42 N42 174.5(3) . . ?
C31 N32 C32 122.8(3) . . ?
C32 N33 Cd1 137.5(2) . 1_655 ?
N41 C41 N42 175.1(3) . . ?
C31 N31 Cd1 152.7(3) . . ?
N21 C22 N25 122.6(3) . . ?
N24 C22 N21 112.8(2) . . ?
N24 C22 N25 124.6(2) . . ?
N11 C12 N15 122.9(2) . . ?
N14 C12 N11 111.6(2) . . ?
N14 C12 N15 125.5(2) . . ?
N31 C31 N32 172.2(3) . . ?
N33 C32 N32 172.2(3) . . ?
C22 N25 H25A 107.5 . . ?
C22 N25 H25B 110.7 . . ?
H25A N25 H25B 108.4 . . ?
N23 C21 H21A 109.5 . . ?
N23 C21 H21B 109.5 . . ?
N23 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N13 C11 H11A 109.5 . . ?
N13 C11 H11B 109.5 . . ?
N13 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
Cd2 N21 N22 N23 -177.99(15) . . . . ?
Cd2 N21 C22 N24 177.66(16) . . . . ?
Cd2 N21 C22 N25 0.2(4) . . . . ?
Cd1 N11 N12 N13 -173.70(16) . . . . ?
Cd1 N11 C12 N14 171.56(17) . . . . ?
Cd1 N11 C12 N15 -9.7(4) . . . . ?
N23 N24 C22 N21 0.2(3) . . . . ?
N23 N24 C22 N25 177.6(3) . . . . ?
N14 N13 N12 N11 0.4(3) . . . . ?
N22 N21 C22 N24 -0.4(3) . . . . ?
N22 N21 C22 N25 -177.8(3) . . . . ?
N22 N23 N24 C22 0.1(3) . . . . ?
N24 N23 N22 N21 -0.3(3) . . . . ?
N13 N14 C12 N11 0.1(3) . . . . ?
N13 N14 C12 N15 -178.6(2) . . . . ?
N12 N11 C12 N14 0.1(3) . . . . ?
N12 N11 C12 N15 178.8(2) . . . . ?
C22 N21 N22 N23 0.4(3) . . . . ?
C12 N11 N12 N13 -0.3(3) . . . . ?
C12 N14 N13 N12 -0.4(3) . . . . ?
C12 N14 N13 C11 -177.9(3) . . . . ?
C21 N23 N22 N21 179.2(2) . . . . ?
C21 N23 N24 C22 -179.4(2) . . . . ?
C11 N13 N12 N11 178.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.584
_oxdiff_exptl_absorpt_empirical_full_min 0.636
####################################################################### 
# 
# 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_xhh-129131_autored
_database_code_depnum_ccdc_archive 'CCDC 2167316'
loop_
_audit_author_name
_audit_author_address
'Haohui Xie'
;FAFU
China
;
_audit_update_record             
;
2022-10-31 deposited with the CCDC.	2022-12-14 downloaded from the CCDC.
;
_audit_creation_date             2022-06-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H5 Cu N11'
_chemical_formula_sum            'C6 H5 Cu N11'
_chemical_formula_weight         294.75
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.5555(6)
_cell_length_b                   7.8169(3)
_cell_length_c                   11.9927(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.854(4)
_cell_angle_gamma                90
_cell_volume                     1080.83(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4305
_cell_measurement_temperature    296.76(10)
_cell_measurement_theta_max      27.1830
_cell_measurement_theta_min      1.7570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.024
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.805
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8589
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.805
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.355
_diffrn_reflns_theta_min         1.766
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.76(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.805
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  25.00   0.50    0.63    --  -11.30 -99.00 -60.00   70
  2  ω    -11.00  14.00   0.50    0.63    --  -11.30 -99.00  30.00   50
  3  ω    -10.00  55.00   0.50    0.63    --   10.52 -99.00  90.00  130
  4  ω    -41.00  47.00   0.50    0.63    --   10.52 -82.00 171.00  176
  5  ω     15.00  82.00   0.50    0.63    --   10.52  57.00 -90.00  134
  6  ω     -2.00  36.00   0.50    0.63    --  -11.30  82.00 -66.00   76
  7  ω    -35.00  -9.00   0.50    0.63    --  -11.30  82.00 -66.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0419190000
_diffrn_orient_matrix_UB_12      0.0461717000
_diffrn_orient_matrix_UB_13      0.0284625000
_diffrn_orient_matrix_UB_21      0.0420245000
_diffrn_orient_matrix_UB_22      0.0636188000
_diffrn_orient_matrix_UB_23      0.0148763000
_diffrn_orient_matrix_UB_31      -0.0162542000
_diffrn_orient_matrix_UB_32      0.0453628000
_diffrn_orient_matrix_UB_33      -0.0497811000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1850
_reflns_number_total             2394
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.077
_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)+(0.0505P)²+0.1891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1023
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed X: Cu1(0.16148)
 Fixed Y: Cu1(0.39067)
 Fixed Z: N15(0.38495)
3.a X=CH2 refined with riding coordinates:
 N25(H25a,H25b)
3.b Idealised Me refined as rotating group:
 C22(H22a,H22b,H22c)
;
_atom_sites_solution_hydrogens   geom
_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
Cu1 Cu 0.161481 0.390670 0.54922(3) 0.03475(15) Uani 1 1 d . . . . .
N21 N 0.3420(2) 0.3146(3) 0.5194(2) 0.0413(6) Uani 1 1 d . . . . .
N16 N 0.1918(2) 0.9917(3) 0.1945(2) 0.0449(6) Uani 1 1 d . . . . .
N13 N 0.1257(2) 0.1787(3) 0.6300(2) 0.0464(7) Uani 1 1 d . . . . .
N14 N 0.1727(3) 0.6069(3) 0.4675(2) 0.0487(7) Uani 1 1 d . . . . .
N11 N -0.0786(2) -0.2874(3) 0.5857(2) 0.0451(7) Uani 1 1 d . . . . .
N12 N 0.0731(3) -0.1115(3) 0.6794(2) 0.0508(8) Uani 1 1 d . . . . .
N24 N 0.4996(2) 0.2407(4) 0.4449(2) 0.0510(7) Uani 1 1 d . . . . .
N15 N 0.1890(3) 0.8881(3) 0.384950 0.0527(8) Uani 1 1 d . . . . .
N25 N 0.3394(3) 0.3159(4) 0.3212(2) 0.0611(8) Uani 1 1 d . . . . .
H25A H 0.268652 0.350309 0.313656 0.073 Uiso 1 1 calc R U . . .
H25B H 0.377383 0.297484 0.263121 0.073 Uiso 1 1 calc R U . . .
N22 N 0.4271(3) 0.2800(5) 0.5994(2) 0.0623(9) Uani 1 1 d . . . . .
C11 C -0.0086(3) -0.1999(4) 0.6264(2) 0.0389(7) Uani 1 1 d . . . . .
C14 C 0.1907(3) 0.9327(3) 0.2814(3) 0.0359(7) Uani 1 1 d . . . . .
C13 C 0.1804(3) 0.7334(4) 0.4214(2) 0.0393(7) Uani 1 1 d . . . . .
C12 C 0.0966(3) 0.0427(4) 0.6489(2) 0.0374(7) Uani 1 1 d . . . . .
C21 C 0.3905(3) 0.2911(4) 0.4234(2) 0.0396(7) Uani 1 1 d . . . . .
N23 N 0.5214(3) 0.2347(6) 0.5568(3) 0.0765(11) Uani 1 1 d . . . . .
C22 C 0.5868(3) 0.1972(7) 0.3678(3) 0.0767(13) Uani 1 1 d . . . . .
H22A H 0.554862 0.117272 0.313272 0.115 Uiso 1 1 calc R U . . .
H22B H 0.652666 0.146746 0.408363 0.115 Uiso 1 1 calc R U . . .
H22C H 0.610643 0.298935 0.330707 0.115 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N21 2.221(3) . ?
Cu1 N16 1.981(3) 4_576 ?
Cu1 N13 1.977(3) . ?
Cu1 N14 1.962(2) . ?
Cu1 N11 1.995(3) 3_556 ?
N21 N22 1.354(4) . ?
N21 C21 1.327(4) . ?
N16 C14 1.141(4) . ?
N13 C12 1.142(4) . ?
N14 C13 1.139(4) . ?
N11 C11 1.144(4) . ?
N12 C11 1.300(4) . ?
N12 C12 1.293(4) . ?
N24 C21 1.329(4) . ?
N24 N23 1.351(4) . ?
N24 C22 1.454(5) . ?
N15 C14 1.291(3) . ?
N15 C13 1.292(4) . ?
N25 H25A 0.8600 . ?
N25 H25B 0.8600 . ?
N25 C21 1.338(4) . ?
N22 N23 1.283(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
N16 Cu1 N21 98.83(10) 4_576 . ?
N16 Cu1 N11 161.52(11) 4_576 3_556 ?
N13 Cu1 N21 94.84(11) . . ?
N13 Cu1 N16 89.35(10) . 4_576 ?
N13 Cu1 N11 87.33(10) . 3_556 ?
N14 Cu1 N21 93.19(12) . . ?
N14 Cu1 N16 91.48(10) . 4_576 ?
N14 Cu1 N13 171.71(13) . . ?
N14 Cu1 N11 89.29(11) . 3_556 ?
N11 Cu1 N21 99.56(10) 3_556 . ?
N22 N21 Cu1 125.8(2) . . ?
C21 N21 Cu1 129.3(2) . . ?
C21 N21 N22 104.9(3) . . ?
C14 N16 Cu1 168.4(3) . 4_575 ?
C12 N13 Cu1 162.1(2) . . ?
C13 N14 Cu1 178.9(3) . . ?
C11 N11 Cu1 151.1(3) . 3_556 ?
C12 N12 C11 121.1(3) . . ?
C21 N24 N23 108.3(3) . . ?
C21 N24 C22 129.5(3) . . ?
N23 N24 C22 122.2(3) . . ?
C14 N15 C13 125.8(2) . . ?
H25A N25 H25B 120.0 . . ?
C21 N25 H25A 120.0 . . ?
C21 N25 H25B 120.0 . . ?
N23 N22 N21 111.6(3) . . ?
N11 C11 N12 174.8(3) . . ?
N16 C14 N15 171.8(3) . . ?
N14 C13 N15 170.7(3) . . ?
N13 C12 N12 173.4(3) . . ?
N21 C21 N24 108.9(3) . . ?
N21 C21 N25 126.0(3) . . ?
N24 C21 N25 125.1(3) . . ?
N22 N23 N24 106.2(3) . . ?
N24 C22 H22A 109.5 . . ?
N24 C22 H22B 109.5 . . ?
N24 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
Cu1 N21 N22 N23 178.1(3) . . . . ?
Cu1 N21 C21 N24 -178.0(2) . . . . ?
Cu1 N21 C21 N25 2.9(5) . . . . ?
N21 N22 N23 N24 0.6(5) . . . . ?
N22 N21 C21 N24 1.3(3) . . . . ?
N22 N21 C21 N25 -177.8(3) . . . . ?
C21 N21 N22 N23 -1.2(4) . . . . ?
C21 N24 N23 N22 0.2(4) . . . . ?
N23 N24 C21 N21 -1.0(4) . . . . ?
N23 N24 C21 N25 178.1(3) . . . . ?
C22 N24 C21 N21 179.2(4) . . . . ?
C22 N24 C21 N25 -1.7(6) . . . . ?
C22 N24 N23 N22 -179.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.345
_oxdiff_exptl_absorpt_empirical_full_min 0.798
