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

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

data_z20180128c_0m
_database_code_depnum_ccdc_archive 'CCDC 1957889'
loop_
_audit_author_name
_audit_author_address
'Shaowei Zhang'
;Hunan University of Science and Technology
China
;
_audit_update_record             
;
2019-10-07 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;
_audit_creation_date             2019-10-07
_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         'C12 H11 Cu N O9, 4(H2 O), 0.75(O)'
_chemical_formula_sum            'C12 H19 Cu N O13.75'
_chemical_formula_weight         460.82
_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      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                   16.3837(3)
_cell_length_b                   17.1120(4)
_cell_length_c                   13.3343(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.6830(10)
_cell_angle_gamma                90
_cell_volume                     3712.97(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2763
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.83
_cell_measurement_theta_min      2.21
_shelx_estimated_absorpt_T_max   0.907
_shelx_estimated_absorpt_T_min   0.754
_exptl_absorpt_coefficient_mu    1.249
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5811
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0799 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.7793.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1896
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   0.7457
_exptl_transmission_factor_min   0.5811
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17333
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.006
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_min         1.727
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2661
_reflns_number_total             3231
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         1.083
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3231
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0752
_refine_ls_restrained_S_all      1.166
_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)+(0.0121P)²+66.2333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1570
_refine_ls_wR_factor_ref         0.1700
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O14) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(O15) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(O13) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(O16) \\sim Ueq, Uanis(O17) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
3. Others
 Fixed Sof: O13(0.3) H13A(0.3) H13B(0.3) O14(0.7) H14A(0.7) H14B(0.7)
 O15(0.25) O16(0.25) O17(0.25)
4.a Free rotating group:
 O10(H10C,H10D), O11(H11A,H11B), O12(H12C,H12D), O13(H13A,H13B), O14(H14A,H14B)
4.b Rotating group:
 O9(H9A,H9B)
4.c Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B)
4.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C8(H8)
4.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.500000 0.22867(6) 0.250000 0.0242(3) Uani 1 2 d S T P . .
Cu2 Cu 0.500000 0.000000 0.500000 0.0435(4) Uani 1 2 d S T P . .
O1 O 0.2528(3) 0.4414(3) 0.3721(5) 0.0557(16) Uani 1 1 d . . . . .
H1 H 0.206441 0.460004 0.367056 0.084 Uiso 1 1 calc GR . . . .
O2 O 0.2900(4) 0.5666(3) 0.3922(5) 0.0572(16) Uani 1 1 d . . . . .
O3 O 0.5728(4) 0.6397(3) 0.3496(5) 0.0598(17) Uani 1 1 d . . . . .
H3 H 0.605256 0.665708 0.321051 0.090 Uiso 1 1 calc GR . . . .
O4 O 0.6698(3) 0.5479(3) 0.3545(5) 0.0531(15) Uani 1 1 d . . . . .
O5 O 0.7331(3) 0.2828(4) 0.3372(4) 0.0536(16) Uani 1 1 d . . . . .
O6 O 0.6175(3) 0.2401(3) 0.2515(3) 0.0339(11) Uani 1 1 d . . . . .
O7 O 0.5080(3) 0.1376(3) 0.3607(4) 0.0366(11) Uani 1 1 d . . . . .
O8 O 0.4901(3) 0.1118(3) 0.5194(4) 0.0367(11) Uani 1 1 d . . . . .
O9 O 0.6001(3) 0.0039(3) 0.5946(4) 0.0422(13) Uani 1 1 d . . . . .
H9A H 0.624992 -0.040951 0.592846 0.063 Uiso 1 1 d GR . . . .
H9B H 0.591009 0.008019 0.657233 0.063 Uiso 1 1 d GR . . . .
O10 O 0.8135(3) 0.3833(3) 0.4718(4) 0.0469(14) Uani 1 1 d . . . . .
H10C H 0.776311 0.380083 0.421826 0.070 Uiso 1 1 d G . . . .
H10D H 0.851513 0.413368 0.456870 0.070 Uiso 1 1 d G . . . .
O11 O 0.8062(4) 0.6337(4) 0.3727(5) 0.0615(17) Uani 1 1 d . . . . .
H11A H 0.831863 0.640922 0.321595 0.092 Uiso 1 1 d G . . . .
H11B H 0.761109 0.610632 0.354387 0.092 Uiso 1 1 d G . . . .
O12 O 0.5970(4) -0.0053(4) 0.3421(6) 0.073(2) Uani 1 1 d . . . . .
H12C H 0.574502 0.038549 0.326983 0.109 Uiso 1 1 d G . . . .
H12D H 0.565249 -0.038574 0.310140 0.109 Uiso 1 1 d G . . . .
O13 O 0.6099(17) 0.2340(17) 0.726(2) 0.077(7) Uani 0.3 1 d . U . A 1
H13A H 0.599550 0.252166 0.666702 0.116 Uiso 0.3 1 d G . . A 1
H13B H 0.660761 0.223498 0.737929 0.116 Uiso 0.3 1 d G . . A 1
O14 O 0.3512(7) 0.2377(7) 0.7036(9) 0.076(3) Uani 0.7 1 d . U . B 2
H14A H 0.383064 0.202914 0.731588 0.114 Uiso 0.7 1 d G . . B 2
H14B H 0.333264 0.223269 0.644180 0.114 Uiso 0.7 1 d G . . B 2
O15 O 0.250000 0.250000 0.500000 0.075(5) Uani 0.5 2 d S TU P . .
O16 O 0.514(3) 0.1460(19) 0.730(3) 0.051(11) Uani 0.25 1 d . U . C 1
O17 O 0.475(2) 0.1300(19) 0.758(3) 0.044(9) Uani 0.25 1 d . U . D 2
N1 N 0.5254(3) 0.2925(3) 0.3991(4) 0.0268(12) Uani 1 1 d . . . . .
C1 C 0.3074(4) 0.4981(4) 0.3818(6) 0.0373(17) Uani 1 1 d . . . . .
C2 C 0.5974(4) 0.5698(4) 0.3573(5) 0.0305(15) Uani 1 1 d . . . . .
C3 C 0.3944(4) 0.4724(4) 0.3814(5) 0.0281(14) Uani 1 1 d . . . . .
C4 C 0.4524(4) 0.5298(4) 0.3747(5) 0.0298(14) Uani 1 1 d . . . . .
H4 H 0.437078 0.582134 0.373678 0.036 Uiso 1 1 calc R . . . .
C5 C 0.5329(4) 0.5096(4) 0.3696(5) 0.0259(14) Uani 1 1 d . . . . .
C6 C 0.5574(4) 0.4310(4) 0.3764(5) 0.0258(14) Uani 1 1 d . . . . .
H6 H 0.611893 0.417534 0.372020 0.031 Uiso 1 1 calc R . . . .
C7 C 0.4996(4) 0.3733(4) 0.3897(5) 0.0259(14) Uani 1 1 d . . . . .
C8 C 0.4169(4) 0.3946(4) 0.3888(5) 0.0298(15) Uani 1 1 d . . . . .
H8 H 0.377207 0.356322 0.393267 0.036 Uiso 1 1 calc R . . . .
C9 C 0.6580(4) 0.2691(4) 0.3302(5) 0.0298(14) Uani 1 1 d . . . . .
C10 C 0.6147(4) 0.2805(4) 0.4235(5) 0.0289(14) Uani 1 1 d . . . . .
H10A H 0.624041 0.234918 0.466649 0.035 Uiso 1 1 calc R . . . .
H10B H 0.638202 0.325338 0.460816 0.035 Uiso 1 1 calc R . . . .
C11 C 0.4949(4) 0.1579(4) 0.4469(5) 0.0265(14) Uani 1 1 d . . . . .
C12 C 0.4822(4) 0.2437(4) 0.4695(5) 0.0306(15) Uani 1 1 d . . . . .
H12A H 0.423999 0.255778 0.461048 0.037 Uiso 1 1 calc R . . . .
H12B H 0.503890 0.255028 0.538755 0.037 Uiso 1 1 calc 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
Cu1 O6 1.933(4) 2_655 ?
Cu1 O6 1.933(4) . ?
Cu1 O7 2.140(5) . ?
Cu1 O7 2.140(5) 2_655 ?
Cu1 N1 2.264(6) 2_655 ?
Cu1 N1 2.264(6) . ?
Cu2 O8 1.940(5) . ?
Cu2 O8 1.940(5) 5_656 ?
Cu2 O9 1.951(5) . ?
Cu2 O9 1.951(5) 5_656 ?
O1 H1 0.8200 . ?
O1 C1 1.316(9) . ?
O2 C1 1.217(9) . ?
O3 H3 0.8200 . ?
O3 C2 1.262(8) . ?
O4 C2 1.248(9) . ?
O5 C9 1.246(8) . ?
O6 C9 1.274(8) . ?
O7 C11 1.242(8) . ?
O8 C11 1.257(8) . ?
O9 H9A 0.8702 . ?
O9 H9B 0.8679 . ?
O10 H10C 0.8507 . ?
O10 H10D 0.8500 . ?
O11 H11A 0.8504 . ?
O11 H11B 0.8478 . ?
O12 H12C 0.8501 . ?
O12 H12D 0.8509 . ?
O13 H13A 0.8507 . ?
O13 H13B 0.8497 . ?
O14 H14A 0.8494 . ?
O14 H14B 0.8498 . ?
O16 O16 0.73(8) 2_656 ?
O17 O17 0.87(7) 2_656 ?
N1 C7 1.446(8) . ?
N1 C10 1.476(8) . ?
N1 C12 1.494(8) . ?
C1 C3 1.492(9) . ?
C2 C5 1.500(9) . ?
C3 C4 1.376(9) . ?
C3 C8 1.383(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(9) . ?
C5 C6 1.403(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.395(9) . ?
C7 C8 1.401(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.515(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.518(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Cu1 O6 168.4(3) 2_655 . ?
O6 Cu1 O7 93.55(19) . 2_655 ?
O6 Cu1 O7 94.89(19) . . ?
O6 Cu1 O7 94.89(19) 2_655 2_655 ?
O6 Cu1 O7 93.55(19) 2_655 . ?
O6 Cu1 N1 92.37(19) . 2_655 ?
O6 Cu1 N1 82.02(19) . . ?
O6 Cu1 N1 92.37(19) 2_655 . ?
O6 Cu1 N1 82.02(19) 2_655 2_655 ?
O7 Cu1 O7 86.6(3) 2_655 . ?
O7 Cu1 N1 75.81(18) 2_655 2_655 ?
O7 Cu1 N1 75.81(18) . . ?
O7 Cu1 N1 161.33(18) 2_655 . ?
O7 Cu1 N1 161.33(18) . 2_655 ?
N1 Cu1 N1 122.3(3) 2_655 . ?
O8 Cu2 O8 180.0 . 5_656 ?
O8 Cu2 O9 87.6(2) . . ?
O8 Cu2 O9 87.6(2) 5_656 5_656 ?
O8 Cu2 O9 92.4(2) 5_656 . ?
O8 Cu2 O9 92.4(2) . 5_656 ?
O9 Cu2 O9 180.0 5_656 . ?
C1 O1 H1 109.5 . . ?
C2 O3 H3 109.5 . . ?
C9 O6 Cu1 118.0(4) . . ?
C11 O7 Cu1 115.6(4) . . ?
C11 O8 Cu2 120.1(5) . . ?
Cu2 O9 H9A 108.3 . . ?
Cu2 O9 H9B 113.5 . . ?
H9A O9 H9B 103.4 . . ?
H10C O10 H10D 109.4 . . ?
H11A O11 H11B 109.4 . . ?
H12C O12 H12D 104.4 . . ?
H13A O13 H13B 109.4 . . ?
H14A O14 H14B 109.4 . . ?
C7 N1 Cu1 111.2(4) . . ?
C7 N1 C10 115.1(5) . . ?
C7 N1 C12 115.7(5) . . ?
C10 N1 Cu1 101.7(4) . . ?
C10 N1 C12 108.2(5) . . ?
C12 N1 Cu1 103.3(4) . . ?
O1 C1 C3 114.8(6) . . ?
O2 C1 O1 123.8(7) . . ?
O2 C1 C3 121.4(7) . . ?
O3 C2 C5 115.9(6) . . ?
O4 C2 O3 125.3(7) . . ?
O4 C2 C5 118.8(6) . . ?
C4 C3 C1 117.2(6) . . ?
C4 C3 C8 120.7(6) . . ?
C8 C3 C1 122.1(6) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.9(6) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C2 121.7(6) . . ?
C4 C5 C6 120.5(6) . . ?
C6 C5 C2 117.7(6) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.6(6) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 N1 119.5(6) . . ?
C6 C7 C8 119.0(6) . . ?
C8 C7 N1 121.5(5) . . ?
C3 C8 C7 120.1(6) . . ?
C3 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
O5 C9 O6 123.4(6) . . ?
O5 C9 C10 117.8(6) . . ?
O6 C9 C10 118.6(6) . . ?
N1 C10 C9 112.5(5) . . ?
N1 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
O7 C11 O8 124.7(6) . . ?
O7 C11 C12 119.7(6) . . ?
O8 C11 C12 115.6(6) . . ?
N1 C12 C11 109.3(5) . . ?
N1 C12 H12A 109.8 . . ?
N1 C12 H12B 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?

_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_z20180412a_0m
_database_code_depnum_ccdc_archive 'CCDC 1957890'
loop_
_audit_author_name
_audit_author_address
'Shaowei Zhang'
;Hunan University of Science and Technology
China
;
_audit_update_record             
;
2019-10-07 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;
_audit_creation_date             2019-09-06
_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         'C12 H13 Cu2 N O11'
_chemical_formula_sum            'C12 H13 Cu2 N O11'
_chemical_formula_weight         474.31
_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                   7.5140(4)
_cell_length_b                   9.0832(5)
_cell_length_c                   11.5882(7)
_cell_angle_alpha                73.946(2)
_cell_angle_beta                 89.605(2)
_cell_angle_gamma                87.875(2)
_cell_volume                     759.54(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    943
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.27
_shelx_estimated_absorpt_T_max   0.847
_shelx_estimated_absorpt_T_min   0.501
_exptl_absorpt_coefficient_mu    2.866
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6623
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0544 before and 0.0427 after correction.
The Ratio of minimum to maximum transmission is 0.8883.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    2.074
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Sheet
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.6623
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5698
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.008
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_min         1.829
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2080
_reflns_number_total             2630
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.565
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2630
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.045
_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)+(0.0411P)²+0.6534P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0929
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Rigid bond restraints
 Cu1, O9
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3.a Rotating group:
 O9(H9A,H9B), O10(H10A,H10B), O11(H11A,H11B)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.65916(6) 0.61388(6) 0.21966(5) 0.01814(17) Uani 1 1 d . U . . .
Cu2 Cu 0.02533(7) 0.16479(6) 0.76684(5) 0.02330(18) Uani 1 1 d . . . . .
O1 O 0.9186(4) 0.6197(3) 0.2503(3) 0.0194(7) Uani 1 1 d . . . . .
O2 O 1.1375(4) 0.5323(4) 0.3822(3) 0.0295(8) Uani 1 1 d . . . . .
O3 O 0.6876(4) 0.5625(3) 0.0689(3) 0.0246(7) Uani 1 1 d . . . . .
O4 O 0.8074(4) 0.4175(4) -0.0382(3) 0.0305(8) Uani 1 1 d . . . . .
O5 O 0.3485(4) 0.0054(4) 0.1402(3) 0.0270(7) Uani 1 1 d . . . . .
O6 O 0.1196(4) -0.0090(4) 0.2667(3) 0.0288(8) Uani 1 1 d . . . . .
O7 O 0.1717(4) 0.1562(4) 0.6310(3) 0.0262(7) Uani 1 1 d . . . . .
O8 O 0.3891(4) 0.3184(4) 0.6386(3) 0.0254(7) Uani 1 1 d . . . . .
O9 O 0.6905(4) 0.8787(4) 0.1158(3) 0.0300(7) Uani 1 1 d . U . . .
H9A H 0.776078 0.917234 0.147246 0.045 Uiso 1 1 d GR . . . .
H9B H 0.592129 0.930593 0.120432 0.045 Uiso 1 1 d GR . . . .
O10 O 0.4047(4) 0.5905(4) 0.2137(3) 0.0378(9) Uani 1 1 d . . . . .
H10A H 0.368729 0.622316 0.141329 0.057 Uiso 1 1 d GR . . . .
H10B H 0.352592 0.642815 0.255336 0.057 Uiso 1 1 d GR . . . .
O11 O -0.0894(4) 0.1560(4) 0.9179(3) 0.0276(7) Uani 1 1 d . . . . .
H11A H -0.186598 0.104836 0.925512 0.041 Uiso 1 1 d GR . . . .
H11B H -0.117768 0.247906 0.922373 0.041 Uiso 1 1 d GR . . . .
N1 N 0.7781(4) 0.3463(4) 0.2847(3) 0.0179(8) Uani 1 1 d . . . . .
C1 C 0.9995(5) 0.5125(5) 0.3338(4) 0.0197(10) Uani 1 1 d . . . . .
C2 C 0.9139(6) 0.3596(5) 0.3702(4) 0.0199(10) Uani 1 1 d . . . . .
H2A H 1.004860 0.279089 0.376614 0.024 Uiso 1 1 calc R . . . .
H2B H 0.860154 0.345311 0.448731 0.024 Uiso 1 1 calc R . . . .
C3 C 0.8548(6) 0.3316(5) 0.1718(4) 0.0216(10) Uani 1 1 d . . . . .
H3A H 0.838242 0.228263 0.166571 0.026 Uiso 1 1 calc R . . . .
H3B H 0.981923 0.346333 0.172970 0.026 Uiso 1 1 calc R . . . .
C4 C 0.7746(5) 0.4447(5) 0.0603(4) 0.0202(10) Uani 1 1 d . . . . .
C5 C 0.2746(6) 0.0305(5) 0.2311(4) 0.0200(10) Uani 1 1 d . . . . .
C6 C 0.3113(5) 0.2275(5) 0.5921(4) 0.0199(10) Uani 1 1 d . . . . .
C7 C 0.6216(5) 0.2638(5) 0.3303(4) 0.0172(9) Uani 1 1 d . . . . .
C8 C 0.5304(5) 0.1855(5) 0.2625(4) 0.0182(9) Uani 1 1 d . . . . .
H8 H 0.574485 0.182069 0.188039 0.022 Uiso 1 1 calc R . . . .
C9 C 0.3731(5) 0.1123(5) 0.3056(4) 0.0170(9) Uani 1 1 d . . . . .
C10 C 0.3051(5) 0.1182(5) 0.4153(4) 0.0172(9) Uani 1 1 d . . . . .
H10 H 0.203463 0.065854 0.445794 0.021 Uiso 1 1 calc R . . . .
C11 C 0.3911(5) 0.2040(5) 0.4800(4) 0.0168(9) Uani 1 1 d . . . . .
C12 C 0.5472(5) 0.2754(5) 0.4370(4) 0.0192(10) Uani 1 1 d . . . . .
H12 H 0.603148 0.332289 0.480743 0.023 Uiso 1 1 calc 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
Cu1 O1 1.989(3) . ?
Cu1 O3 1.937(3) . ?
Cu1 O8 1.935(3) 2_666 ?
Cu1 O9 2.393(3) . ?
Cu1 O10 1.935(3) . ?
Cu1 N1 2.472(4) . ?
Cu2 O1 1.974(3) 2_666 ?
Cu2 O6 1.940(3) 2_556 ?
Cu2 O7 1.932(3) . ?
Cu2 H9A 1.82(3) 2_666 ?
Cu2 O11 1.929(3) . ?
O1 C1 1.303(5) . ?
O2 C1 1.225(5) . ?
O3 C4 1.261(5) . ?
O4 C4 1.254(5) . ?
O5 C5 1.259(5) . ?
O6 C5 1.264(5) . ?
O7 C6 1.267(5) . ?
O8 C6 1.265(5) . ?
O9 H9A 0.8720 . ?
O9 H9B 0.8711 . ?
O10 H10A 0.8507 . ?
O10 H10B 0.8502 . ?
O11 H11A 0.8707 . ?
O11 H11B 0.8695 . ?
N1 C2 1.459(5) . ?
N1 C3 1.464(5) . ?
N1 C7 1.436(5) . ?
C1 C2 1.503(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.522(6) . ?
C5 C9 1.499(6) . ?
C6 C11 1.492(6) . ?
C7 C8 1.395(6) . ?
C7 C12 1.382(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.398(6) . ?
C9 C10 1.382(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.397(6) . ?
C11 C12 1.383(6) . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O9 83.54(11) . . ?
O1 Cu1 N1 72.33(11) . . ?
O3 Cu1 O1 95.28(12) . . ?
O3 Cu1 O9 89.56(12) . . ?
O3 Cu1 N1 77.46(12) . . ?
O8 Cu1 O1 89.15(12) 2_666 . ?
O8 Cu1 O3 173.70(13) 2_666 . ?
O8 Cu1 O9 86.49(12) 2_666 . ?
O8 Cu1 O10 85.73(13) 2_666 . ?
O8 Cu1 N1 108.22(13) 2_666 . ?
O9 Cu1 N1 151.16(11) . . ?
O10 Cu1 O1 171.72(14) . . ?
O10 Cu1 O3 90.35(13) . . ?
O10 Cu1 O9 102.60(14) . . ?
O10 Cu1 N1 103.12(14) . . ?
O1 Cu2 H9A 95.6(5) 2_666 2_666 ?
O6 Cu2 O1 152.18(14) 2_556 2_666 ?
O6 Cu2 H9A 112.1(5) 2_556 2_666 ?
O7 Cu2 O1 92.29(13) . 2_666 ?
O7 Cu2 O6 88.43(12) . 2_556 ?
O7 Cu2 H9A 83.60(14) . 2_666 ?
O11 Cu2 O1 89.59(12) . 2_666 ?
O11 Cu2 O6 94.09(13) . 2_556 ?
O11 Cu2 O7 170.85(14) . . ?
O11 Cu2 H9A 87.31(14) . 2_666 ?
Cu2 O1 Cu1 107.56(13) 2_666 . ?
C1 O1 Cu1 121.2(3) . . ?
C1 O1 Cu2 118.6(2) . 2_666 ?
C4 O3 Cu1 122.6(3) . . ?
C5 O6 Cu2 129.7(3) . 2_556 ?
C6 O7 Cu2 129.3(3) . . ?
C6 O8 Cu1 132.6(3) . 2_666 ?
Cu1 O9 H9A 110.7 . . ?
Cu1 O9 H9B 110.2 . . ?
H9A O9 H9B 108.2 . . ?
Cu1 O10 H10A 109.5 . . ?
Cu1 O10 H10B 109.2 . . ?
H10A O10 H10B 109.4 . . ?
Cu2 O11 H11A 111.0 . . ?
Cu2 O11 H11B 110.3 . . ?
H11A O11 H11B 108.0 . . ?
C2 N1 Cu1 100.3(2) . . ?
C2 N1 C3 112.3(3) . . ?
C3 N1 Cu1 100.2(2) . . ?
C7 N1 Cu1 102.0(2) . . ?
C7 N1 C2 118.3(3) . . ?
C7 N1 C3 118.9(3) . . ?
O1 C1 C2 116.5(3) . . ?
O2 C1 O1 123.1(4) . . ?
O2 C1 C2 120.4(4) . . ?
N1 C2 C1 112.2(4) . . ?
N1 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N1 C3 H3A 108.7 . . ?
N1 C3 H3B 108.7 . . ?
N1 C3 C4 114.0(3) . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
O3 C4 C3 120.3(4) . . ?
O4 C4 O3 123.0(4) . . ?
O4 C4 C3 116.6(4) . . ?
O5 C5 O6 124.8(4) . . ?
O5 C5 C9 119.5(4) . . ?
O6 C5 C9 115.7(4) . . ?
O7 C6 C11 117.3(4) . . ?
O8 C6 O7 126.2(4) . . ?
O8 C6 C11 116.5(4) . . ?
C8 C7 N1 121.1(4) . . ?
C12 C7 N1 119.9(3) . . ?
C12 C7 C8 118.5(4) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.4(4) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C5 120.1(4) . . ?
C10 C9 C5 119.6(4) . . ?
C10 C9 C8 120.3(4) . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.1(4) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C6 120.8(4) . . ?
C12 C11 C6 119.0(4) . . ?
C12 C11 C10 120.1(4) . . ?
C7 C12 C11 121.3(4) . . ?
C7 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
