# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

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

data_b
_database_code_depnum_ccdc_archive 'CCDC 1944632'
loop_
_audit_author_name
_audit_author_address
'Hui Peng'
;East China Normal University
China
;
_audit_update_record             
;
2019-08-01 deposited with the CCDC.	2019-11-18 downloaded from the CCDC.
;
_audit_creation_date             2017-05-12
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 N4, Cl4 Cu, H2 O'
_chemical_formula_sum            'C14 H18 Cl4 Cu N4 O'
_chemical_formula_weight         463.66
_chemical_absolute_configuration .
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   7.1235(2)
_cell_length_b                   11.1935(4)
_cell_length_c                   11.6744(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.7160(10)
_cell_angle_gamma                90
_cell_volume                     922.45(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8350
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      68.14
_cell_measurement_theta_min      3.82
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.089
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.2746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1449 before and 0.0673 after correction.
The Ratio of minimum to maximum transmission is 0.3647.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             470
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8084
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.185
_diffrn_reflns_theta_min         3.949
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.993
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2979
_reflns_number_total             2993
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.386
_refine_diff_density_min         -0.697
_refine_diff_density_rms         0.120
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.049(18)
_refine_ls_extinction_coef       0.0252(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2993
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.121
_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)+(0.0409P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0678
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.951(18) 0.049(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
3.a Riding coordinates:
 O1(H1A,H1B)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 N4(H4), N2(H2), C1(H1), C6(H6), C10(H10), C7(H7), C11(H11), C12(H12),
 C13(H13), C2(H2A), C14(H14), C3(H3)
;
_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
N1 N 0.9433(4) 0.2836(2) 0.3130(3) 0.0167(6) Uani 1 1 d . . . . .
N4 N 0.3775(4) 0.8544(3) 0.7213(3) 0.0211(6) Uani 1 1 d . . . . .
H4 H 0.3721 0.9310 0.7377 0.025 Uiso 1 1 calc R . . . .
N3 N 0.3608(4) 0.6902(2) 0.6253(3) 0.0140(6) Uani 1 1 d . . . . .
N2 N 0.8625(5) 0.1237(3) 0.2169(3) 0.0260(7) Uani 1 1 d . . . . .
H2 H 0.8380 0.0482 0.2000 0.031 Uiso 1 1 calc R . . . .
C1 C 0.9225(5) 0.1662(3) 0.3220(4) 0.0220(7) Uani 1 1 d . . . . .
H1 H 0.9461 0.1206 0.3911 0.026 Uiso 1 1 calc R . . . .
C6 C 0.7781(5) 0.5442(3) 0.3997(3) 0.0176(7) Uani 1 1 d . . . . .
H6 H 0.8546 0.5832 0.3505 0.021 Uiso 1 1 calc R . . . .
C10 C 0.3377(5) 0.8077(3) 0.6165(3) 0.0183(7) Uani 1 1 d . . . . .
H10 H 0.2993 0.8508 0.5472 0.022 Uiso 1 1 calc R . . . .
C8 C 0.5031(5) 0.5445(3) 0.5014(3) 0.0156(6) Uani 1 1 d . . . . .
C4 C 1.0003(5) 0.3674(3) 0.4098(3) 0.0198(7) Uani 1 1 d . . . . .
H4A H 1.0905 0.4269 0.3861 0.024 Uiso 1 1 calc R . . . .
H4B H 1.0651 0.3227 0.4769 0.024 Uiso 1 1 calc R . . . .
C7 C 0.6148(5) 0.5998(3) 0.4272(3) 0.0190(7) Uani 1 1 d . . . . .
H7 H 0.5793 0.6758 0.3952 0.023 Uiso 1 1 calc R . . . .
C11 C 0.4283(5) 0.7657(3) 0.8001(3) 0.0225(7) Uani 1 1 d . . . . .
H11 H 0.4641 0.7750 0.8810 0.027 Uiso 1 1 calc R . . . .
C9 C 0.3242(5) 0.6037(3) 0.5296(3) 0.0177(7) Uani 1 1 d . . . . .
H9A H 0.2618 0.6454 0.4600 0.021 Uiso 1 1 calc R . . . .
H9B H 0.2361 0.5415 0.5507 0.021 Uiso 1 1 calc R . . . .
C12 C 0.4172(5) 0.6619(3) 0.7399(3) 0.0193(7) Uani 1 1 d . . . . .
H12 H 0.4434 0.5842 0.7707 0.023 Uiso 1 1 calc R . . . .
C5 C 0.8294(5) 0.4312(3) 0.4445(3) 0.0163(6) Uani 1 1 d . . . . .
C13 C 0.5575(5) 0.4325(3) 0.5478(3) 0.0202(7) Uani 1 1 d . . . . .
H13 H 0.4832 0.3942 0.5988 0.024 Uiso 1 1 calc R . . . .
C2 C 0.8448(5) 0.2161(3) 0.1390(3) 0.0246(8) Uani 1 1 d . . . . .
H2A H 0.8051 0.2104 0.0581 0.030 Uiso 1 1 calc R . . . .
C14 C 0.7196(5) 0.3772(3) 0.5196(3) 0.0201(7) Uani 1 1 d . . . . .
H14 H 0.7558 0.3015 0.5520 0.024 Uiso 1 1 calc R . . . .
C3 C 0.8946(6) 0.3163(3) 0.1992(4) 0.0225(7) Uani 1 1 d . . . . .
H3 H 0.8959 0.3950 0.1689 0.027 Uiso 1 1 calc R . . . .
Cu1 Cu 0.21550(6) 0.18741(4) 0.75236(4) 0.01699(18) Uani 1 1 d . . . . .
Cl1 Cl 0.15636(11) 0.38228(6) 0.71749(7) 0.0200(2) Uani 1 1 d . . . . .
Cl2 Cl 0.46228(11) 0.09142(7) 0.85741(7) 0.0208(2) Uani 1 1 d . . . . .
Cl3 Cl -0.00281(11) 0.15133(8) 0.86838(8) 0.0246(2) Uani 1 1 d . . . . .
Cl4 Cl 0.27341(13) 0.12418(8) 0.57764(7) 0.0263(2) Uani 1 1 d . . . . .
O1 O 0.7307(5) 0.0949(3) 0.6345(3) 0.0396(7) Uani 1 1 d . . . . .
H1A H 0.6193 0.1152 0.6091 0.059 Uiso 1 1 d R . . . .
H1B H 0.7804 0.1392 0.6895 0.059 Uiso 1 1 d R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.329(5) . ?
N1 C4 1.483(4) . ?
N1 C3 1.377(5) . ?
N4 H4 0.8800 . ?
N4 C10 1.325(5) . ?
N4 C11 1.369(5) . ?
N3 C10 1.328(4) . ?
N3 C9 1.475(4) . ?
N3 C12 1.380(5) . ?
N2 H2 0.8800 . ?
N2 C1 1.333(5) . ?
N2 C2 1.372(5) . ?
C1 H1 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.393(5) . ?
C6 C5 1.399(5) . ?
C10 H10 0.9500 . ?
C8 C7 1.397(5) . ?
C8 C9 1.511(4) . ?
C8 C13 1.400(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.512(5) . ?
C7 H7 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.355(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C12 H12 0.9500 . ?
C5 C14 1.389(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(5) . ?
C2 H2A 0.9500 . ?
C2 C3 1.347(6) . ?
C14 H14 0.9500 . ?
C3 H3 0.9500 . ?
Cu1 Cl1 2.2483(8) . ?
Cu1 Cl2 2.2738(9) . ?
Cu1 Cl3 2.2320(9) . ?
Cu1 Cl4 2.2489(10) . ?
O1 H1A 0.8402 . ?
O1 H1B 0.8509 . ?

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
C1 N1 C4 126.0(3) . . ?
C1 N1 C3 108.8(3) . . ?
C3 N1 C4 125.1(3) . . ?
C10 N4 H4 125.1 . . ?
C10 N4 C11 109.8(3) . . ?
C11 N4 H4 125.1 . . ?
C10 N3 C9 125.7(3) . . ?
C10 N3 C12 108.6(3) . . ?
C12 N3 C9 125.6(3) . . ?
C1 N2 H2 125.3 . . ?
C1 N2 C2 109.4(3) . . ?
C2 N2 H2 125.3 . . ?
N1 C1 N2 107.8(3) . . ?
N1 C1 H1 126.1 . . ?
N2 C1 H1 126.1 . . ?
C7 C6 H6 119.9 . . ?
C7 C6 C5 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
N4 C10 N3 108.1(3) . . ?
N4 C10 H10 126.0 . . ?
N3 C10 H10 126.0 . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 C13 119.0(3) . . ?
C13 C8 C9 120.4(3) . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 C5 110.8(3) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C6 C7 C8 120.5(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
N4 C11 H11 126.8 . . ?
C12 C11 N4 106.4(3) . . ?
C12 C11 H11 126.8 . . ?
N3 C9 C8 112.6(3) . . ?
N3 C9 H9A 109.1 . . ?
N3 C9 H9B 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
N3 C12 H12 126.4 . . ?
C11 C12 N3 107.2(3) . . ?
C11 C12 H12 126.4 . . ?
C6 C5 C4 120.4(3) . . ?
C14 C5 C6 119.2(3) . . ?
C14 C5 C4 120.4(3) . . ?
C8 C13 H13 119.9 . . ?
C14 C13 C8 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
N2 C2 H2A 126.6 . . ?
C3 C2 N2 106.7(3) . . ?
C3 C2 H2A 126.6 . . ?
C5 C14 H14 119.6 . . ?
C13 C14 C5 120.9(3) . . ?
C13 C14 H14 119.6 . . ?
N1 C3 H3 126.4 . . ?
C2 C3 N1 107.3(3) . . ?
C2 C3 H3 126.4 . . ?
Cl1 Cu1 Cl2 131.96(4) . . ?
Cl1 Cu1 Cl4 101.18(4) . . ?
Cl3 Cu1 Cl1 99.01(3) . . ?
Cl3 Cu1 Cl2 97.95(4) . . ?
Cl3 Cu1 Cl4 136.14(4) . . ?
Cl4 Cu1 Cl2 96.77(3) . . ?
H1A O1 H1B 112.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C4 C5 C6 -95.5(4) . . . . ?
N1 C4 C5 C14 83.3(4) . . . . ?
N4 C11 C12 N3 0.3(4) . . . . ?
N2 C2 C3 N1 0.4(4) . . . . ?
C1 N1 C4 C5 -100.3(4) . . . . ?
C1 N1 C3 C2 -0.4(4) . . . . ?
C1 N2 C2 C3 -0.3(4) . . . . ?
C6 C5 C14 C13 1.8(5) . . . . ?
C10 N4 C11 C12 -0.3(4) . . . . ?
C10 N3 C9 C8 112.9(4) . . . . ?
C10 N3 C12 C11 -0.2(4) . . . . ?
C8 C13 C14 C5 -0.5(5) . . . . ?
C4 N1 C1 N2 177.4(3) . . . . ?
C4 N1 C3 C2 -177.6(3) . . . . ?
C4 C5 C14 C13 -177.0(3) . . . . ?
C7 C6 C5 C4 176.6(3) . . . . ?
C7 C6 C5 C14 -2.2(5) . . . . ?
C7 C8 C9 N3 -84.7(4) . . . . ?
C7 C8 C13 C14 -0.4(5) . . . . ?
C11 N4 C10 N3 0.2(4) . . . . ?
C9 N3 C10 N4 177.6(3) . . . . ?
C9 N3 C12 C11 -177.8(3) . . . . ?
C9 C8 C7 C6 -178.9(3) . . . . ?
C9 C8 C13 C14 178.5(3) . . . . ?
C12 N3 C10 N4 0.0(4) . . . . ?
C12 N3 C9 C8 -69.9(4) . . . . ?
C5 C6 C7 C8 1.3(5) . . . . ?
C13 C8 C7 C6 0.0(5) . . . . ?
C13 C8 C9 N3 96.4(4) . . . . ?
C2 N2 C1 N1 0.1(4) . . . . ?
C3 N1 C1 N2 0.2(4) . . . . ?
C3 N1 C4 C5 76.5(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.951(18)
2 0.049(18)

