# Electronic Supplementary Material (ESI) for Metallomics.
# 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_150116_s2_lzh_m
_audit_block_doi                 10.5517/ccdc.csd.cc1njx03
_database_code_depnum_ccdc_archive 'CCDC 1535585'
_audit_update_record             
;
2017-03-02 deposited with the CCDC.	2019-02-14 downloaded from the CCDC.
;
_audit_creation_date             2015-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C6 H18 Cl Cu N4, Cl, H2 O'
_chemical_formula_sum            'C6 H20 Cl2 Cu N4 O'
_chemical_formula_weight         298.70
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         cu1c10n4h20
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.0684(2)
_cell_length_b                   10.5124(4)
_cell_length_c                   16.5540(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1230.05(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1634
_cell_measurement_temperature    143.00(10)
_cell_measurement_theta_max      28.1190
_cell_measurement_theta_min      3.6670
_shelx_estimated_absorpt_T_max   0.669
_shelx_estimated_absorpt_T_min   0.560
_exptl_absorpt_coefficient_mu    2.188
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3978
_diffrn_reflns_point_group_measured_fraction_full 0.862
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         3.132
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      143.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0094138000
_diffrn_orient_matrix_UB_12      -0.0372730000
_diffrn_orient_matrix_UB_13      0.0355193000
_diffrn_orient_matrix_UB_21      -0.0203950000
_diffrn_orient_matrix_UB_22      -0.0556605000
_diffrn_orient_matrix_UB_23      -0.0225448000
_diffrn_orient_matrix_UB_31      0.0978181000
_diffrn_orient_matrix_UB_32      -0.0080320000
_diffrn_orient_matrix_UB_33      -0.0081084000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.457
_reflns_Friedel_fraction_full    0.669
_reflns_Friedel_fraction_max     0.644
_reflns_number_gt                1964
_reflns_number_total             2139
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 
;
 Flack x determined using 583 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.007(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.039
_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)+(0.0290P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0679
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2), N3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 N1(H1C,H1D), N4(H4C,H4D)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
C1 C -0.3466(6) -0.5730(5) -0.7456(3) 0.0211(11) Uani 1 1 d . . . . .
H1A H -0.4684 -0.5962 -0.7682 0.025 Uiso 1 1 calc R . . . .
H1B H -0.2516 -0.5797 -0.7877 0.025 Uiso 1 1 calc R . . . .
C2 C -0.3528(6) -0.4378(5) -0.7122(3) 0.0197(11) Uani 1 1 d . . . . .
H2A H -0.3796 -0.3774 -0.7550 0.024 Uiso 1 1 calc R . . . .
H2B H -0.4499 -0.4303 -0.6711 0.024 Uiso 1 1 calc R . . . .
C3 C -0.1517(6) -0.3062(5) -0.6194(3) 0.0212(11) Uani 1 1 d . . . . .
H3A H -0.2537 -0.3109 -0.5803 0.025 Uiso 1 1 calc R . . . .
H3B H -0.1607 -0.2257 -0.6478 0.025 Uiso 1 1 calc R . . . .
C4 C 0.0387(7) -0.3175(5) -0.5773(3) 0.0211(11) Uani 1 1 d . . . . .
H4A H 0.1398 -0.3011 -0.6156 0.025 Uiso 1 1 calc R . . . .
H4B H 0.0472 -0.2552 -0.5343 0.025 Uiso 1 1 calc R . . . .
C5 C -0.0122(6) -0.4630(4) -0.4606(3) 0.0164(11) Uani 1 1 d . . . . .
H5A H -0.1376 -0.4265 -0.4555 0.020 Uiso 1 1 calc R . . . .
H5B H 0.0713 -0.4206 -0.4227 0.020 Uiso 1 1 calc R . . . .
C6 C -0.0180(6) -0.6052(4) -0.4434(3) 0.0163(11) Uani 1 1 d . . . . .
H6A H 0.1095 -0.6392 -0.4418 0.020 Uiso 1 1 calc R . . . .
H6B H -0.0768 -0.6205 -0.3913 0.020 Uiso 1 1 calc R . . . .
Cl1 Cl 0.18942(15) -0.66285(12) -0.67956(7) 0.0204(3) Uani 1 1 d . . . . .
Cu1 Cu -0.09168(7) -0.57096(6) -0.61229(3) 0.01405(15) Uani 1 1 d . . . . .
N1 N -0.2985(5) -0.6574(4) -0.6769(2) 0.0176(9) Uani 1 1 d . . . . .
H1C H -0.2548 -0.7392 -0.6966 0.021 Uiso 1 1 calc R . . . .
H1D H -0.4090 -0.6712 -0.6433 0.021 Uiso 1 1 calc R . . . .
N2 N -0.1635(5) -0.4137(4) -0.6772(2) 0.0154(8) Uani 1 1 d . . . . .
H2 H -0.0716 -0.4011 -0.7208 0.019 Uiso 1 1 calc R . . . .
N3 N 0.0584(5) -0.4472(4) -0.5437(2) 0.0157(9) Uani 1 1 d . . . . .
H3 H 0.1922 -0.4716 -0.5453 0.019 Uiso 1 1 calc R . . . .
N4 N -0.1272(5) -0.6685(4) -0.5073(2) 0.0143(8) Uani 1 1 d . . . . .
H4C H -0.2602 -0.6704 -0.4929 0.017 Uiso 1 1 calc R . . . .
H4D H -0.0838 -0.7554 -0.5139 0.017 Uiso 1 1 calc R . . . .
Cl2 Cl -0.51937(14) -0.51640(11) -0.47876(8) 0.0229(3) Uani 1 1 d . . . . .
H1E H -0.131(9) -0.941(7) -0.658(4) 0.07(3) Uiso 1 1 d . . . . .
H1F H -0.184(7) -0.978(5) -0.728(3) 0.017(17) Uiso 1 1 d . . . . .
O1 O -0.1646(6) -0.9247(4) -0.7027(3) 0.0294(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.525(7) . ?
C1 N1 1.482(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N2 1.480(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.520(6) . ?
C3 N2 1.483(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N3 1.480(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.523(6) . ?
C5 N3 1.473(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 N4 1.470(5) . ?
Cl1 Cu1 2.4741(12) . ?
Cu1 N1 2.026(4) . ?
Cu1 N2 2.035(4) . ?
Cu1 N3 2.026(4) . ?
Cu1 N4 2.033(4) . ?
N1 H1C 0.9700 . ?
N1 H1D 0.9700 . ?
N2 H2 0.9800 . ?
N3 H3 0.9800 . ?
N4 H4C 0.9700 . ?
N4 H4D 0.9700 . ?
O1 H1E 0.80(7) . ?
O1 H1F 0.71(5) . ?

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
H1A C1 H1B 108.6 . . ?
C2 C1 H1A 110.4 . . ?
C2 C1 H1B 110.4 . . ?
N1 C1 H1A 110.4 . . ?
N1 C1 H1B 110.4 . . ?
N1 C1 C2 106.6(4) . . ?
C1 C2 H2A 110.5 . . ?
C1 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
N2 C2 C1 106.0(4) . . ?
N2 C2 H2A 110.5 . . ?
N2 C2 H2B 110.5 . . ?
H3A C3 H3B 108.6 . . ?
C4 C3 H3A 110.4 . . ?
C4 C3 H3B 110.4 . . ?
N2 C3 H3A 110.4 . . ?
N2 C3 H3B 110.4 . . ?
N2 C3 C4 106.6(4) . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N3 C4 C3 109.1(4) . . ?
N3 C4 H4A 109.9 . . ?
N3 C4 H4B 109.9 . . ?
H5A C5 H5B 108.5 . . ?
C6 C5 H5A 110.3 . . ?
C6 C5 H5B 110.3 . . ?
N3 C5 H5A 110.3 . . ?
N3 C5 H5B 110.3 . . ?
N3 C5 C6 107.2(4) . . ?
C5 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
N4 C6 C5 108.9(4) . . ?
N4 C6 H6A 109.9 . . ?
N4 C6 H6B 109.9 . . ?
N1 Cu1 Cl1 99.60(11) . . ?
N1 Cu1 N2 84.60(16) . . ?
N1 Cu1 N3 163.99(15) . . ?
N1 Cu1 N4 97.79(15) . . ?
N2 Cu1 Cl1 106.25(11) . . ?
N3 Cu1 Cl1 94.72(10) . . ?
N3 Cu1 N2 84.54(15) . . ?
N3 Cu1 N4 84.82(15) . . ?
N4 Cu1 Cl1 106.67(11) . . ?
N4 Cu1 N2 146.08(15) . . ?
C1 N1 Cu1 107.6(3) . . ?
C1 N1 H1C 110.2 . . ?
C1 N1 H1D 110.2 . . ?
Cu1 N1 H1C 110.2 . . ?
Cu1 N1 H1D 110.2 . . ?
H1C N1 H1D 108.5 . . ?
C2 N2 C3 115.7(4) . . ?
C2 N2 Cu1 107.0(3) . . ?
C2 N2 H2 109.5 . . ?
C3 N2 Cu1 105.4(3) . . ?
C3 N2 H2 109.5 . . ?
Cu1 N2 H2 109.5 . . ?
C4 N3 Cu1 109.4(3) . . ?
C4 N3 H3 108.8 . . ?
C5 N3 C4 115.0(4) . . ?
C5 N3 Cu1 105.9(3) . . ?
C5 N3 H3 108.8 . . ?
Cu1 N3 H3 108.8 . . ?
C6 N4 Cu1 108.8(3) . . ?
C6 N4 H4C 109.9 . . ?
C6 N4 H4D 109.9 . . ?
Cu1 N4 H4C 109.9 . . ?
Cu1 N4 H4D 109.9 . . ?
H4C N4 H4D 108.3 . . ?
H1E O1 H1F 116(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
C1 C2 N2 C3 -161.8(4) . . . . ?
C1 C2 N2 Cu1 -44.7(4) . . . . ?
C2 C1 N1 Cu1 -42.4(4) . . . . ?
C3 C4 N3 C5 -89.9(4) . . . . ?
C3 C4 N3 Cu1 29.1(4) . . . . ?
C4 C3 N2 C2 167.4(4) . . . . ?
C4 C3 N2 Cu1 49.4(4) . . . . ?
C5 C6 N4 Cu1 31.5(4) . . . . ?
C6 C5 N3 C4 168.4(4) . . . . ?
C6 C5 N3 Cu1 47.6(4) . . . . ?
N1 C1 C2 N2 58.3(4) . . . . ?
N2 C3 C4 N3 -52.7(5) . . . . ?
N3 C5 C6 N4 -53.3(5) . . . . ?

