# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1572628'
_audit_update_record             
;
2017-09-05 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H14 Cl0.31 Cu1.31 N2 O5 '
_chemical_formula_sum            'C19 H14 Cl0.31 Cu1.31 N2 O5 '
_chemical_formula_weight         444.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           ?
_space_group_name_H-M_alt        Pcan
_space_group_name_Hall           -P2n2c

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x, y, z-1/2'
'x-1/2, -y-1/2, z'

_cell_length_a                   13.2144(15)
_cell_length_b                   22.3311(11)
_cell_length_c                   23.9725(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7074.1(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2910
_cell_measurement_theta_min      3.3210
_cell_measurement_theta_max      26.4190

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    0.835
_exptl_crystal_F_000             1801.7
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.827
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7920
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.931
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_full        29.12
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             7920
_reflns_number_gt                3534
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1126P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6175
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1910
_refine_ls_wR_factor_gt          0.1754
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.41341(4) 0.02957(2) 0.00242(2) 0.0441(2) Uani 1 1 d . . . . .
O4 O 1.0098(2) 0.40510(10) 0.46737(10) 0.0575(7) Uani 1 1 d . . . . .
O1 O 0.4637(2) 0.05596(12) 0.07559(10) 0.0597(7) Uani 1 1 d . . . . .
O2 O 0.6099(2) 0.00467(12) 0.07183(10) 0.0611(8) Uani 1 1 d . . . . .
O1W O 0.2721(3) 0.07734(15) 0.00994(12) 0.0778(9) Uani 1 1 d . . . . .
C19 C 0.9181(4) 0.40981(18) 0.45562(14) 0.0510(10) Uani 1 1 d . . . . .
C1 C 0.5477(4) 0.03972(16) 0.09508(14) 0.0512(10) Uani 1 1 d . . . . .
C2 C 0.5772(4) 0.06515(17) 0.15067(15) 0.0606(12) Uani 1 1 d . . . . .
N2 N 0.7238(3) 0.20696(15) 0.36002(13) 0.0690(11) Uani 1 1 d . . . . .
C16 C 0.8678(3) 0.35651(16) 0.42939(15) 0.0542(10) Uani 1 1 d . . . . .
N1 N 0.6623(3) 0.14340(14) 0.30216(13) 0.0688(11) Uani 1 1 d . . . . .
C6 C 0.6314(4) 0.11538(19) 0.25073(15) 0.0630(12) Uani 1 1 d . . . . .
C3 C 0.5119(4) 0.1047(2) 0.17837(17) 0.0764(14) Uani 1 1 d . . . . .
H3 H 0.4482 0.1142 0.1623 0.092 Uiso 1 1 calc R U . . .
C12 C 0.7717(4) 0.25960(19) 0.38268(16) 0.0652(13) Uani 1 1 d . . . . .
C17 C 0.9152(4) 0.30251(19) 0.4285(2) 0.0764(14) Uani 1 1 d . . . . .
H17 H 0.9816 0.2985 0.4432 0.092 Uiso 1 1 calc R U . . .
C8 C 0.6693(4) 0.05079(19) 0.17447(16) 0.0657(12) Uani 1 1 d . . . . .
H8 H 0.7138 0.0237 0.1562 0.079 Uiso 1 1 calc R U . . .
C10 C 0.6433(4) 0.12255(19) 0.35502(15) 0.0795(16) Uani 1 1 d . . . . .
H10 H 0.6096 0.0863 0.3643 0.095 Uiso 1 1 calc R U . . .
C11 C 0.6805(4) 0.16182(18) 0.39058(16) 0.0751(15) Uani 1 1 d . . . . .
H11 H 0.6777 0.1593 0.4301 0.090 Uiso 1 1 calc R U . . .
C7 C 0.6963(4) 0.0759(2) 0.22448(17) 0.0745(14) Uani 1 1 d . . . . .
H7 H 0.7595 0.0661 0.2411 0.089 Uiso 1 1 calc R U . . .
C4 C 0.5389(5) 0.1298(2) 0.22846(19) 0.0805(15) Uani 1 1 d . . . . .
C13 C 0.7235(4) 0.3139(2) 0.3806(2) 0.0839(15) Uani 1 1 d . . . . .
C9 C 0.7128(4) 0.1957(2) 0.30513(17) 0.0762(14) Uani 1 1 d . . . . .
C15 C 0.7746(4) 0.3626(2) 0.4051(2) 0.0765(14) Uani 1 1 d . . . . .
H15 H 0.7434 0.4010 0.4046 0.092 Uiso 1 1 calc R U . . .
C18 C 0.8650(4) 0.25277(19) 0.4058(2) 0.0828(15) Uani 1 1 d . . . . .
H18 H 0.8961 0.2144 0.4065 0.099 Uiso 1 1 calc R U . . .
O3 O 0.8634(2) 0.45545(12) 0.46295(11) 0.0602(7) Uani 1 1 d . . . . .
C14 C 0.6211(6) 0.3218(3) 0.3533(4) 0.144(3) Uani 1 1 d . . . . .
H14A H 0.6274 0.3156 0.3130 0.216 Uiso 1 1 calc R U . . .
H14B H 0.5962 0.3624 0.3605 0.216 Uiso 1 1 calc R U . . .
H14C H 0.5734 0.2926 0.3688 0.216 Uiso 1 1 calc R U . . .
C5 C 0.4683(6) 0.1743(3) 0.2579(3) 0.142(3) Uani 1 1 d . . . . .
H5A H 0.3989 0.1684 0.2447 0.214 Uiso 1 1 calc R U . . .
H5B H 0.4900 0.2153 0.2497 0.214 Uiso 1 1 calc R U . . .
H5C H 0.4710 0.1675 0.2983 0.214 Uiso 1 1 calc R U . . .
Cu2 Cu 0.7275(3) 0.24807(14) 0.24402(11) 0.160(2) Uani 0.309(3) 1 d . . P . .
Cl1 Cl 0.7430(9) 0.3086(5) 0.1717(6) 0.240 Uiso 0.309(3) 1 d . U P . .


_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 O2 1.961(2) 5_655 ?
Cu1 O3 1.966(2) 6_556 ?
Cu1 O1 1.966(2) . ?
Cu1 O4 1.966(2) 2_654 ?
Cu1 O1W 2.158(3) . ?
Cu1 Cu1 2.6447(10) 5_655 ?
O4 C19 1.249(5) . ?
O4 Cu1 1.966(2) 2_655 ?
O1 C1 1.258(5) . ?
O2 C1 1.264(5) . ?
O2 Cu1 1.962(2) 5_655 ?
C19 O3 1.262(5) . ?
C19 C16 1.501(5) . ?
C1 C2 1.500(5) . ?
C2 C8 1.382(6) . ?
C2 C3 1.402(6) . ?
N2 C9 1.347(5) . ?
N2 C11 1.371(5) . ?
N2 C12 1.442(5) . ?
C16 C17 1.359(6) . ?
C16 C15 1.369(6) . ?
N1 C9 1.347(5) . ?
N1 C10 1.373(5) . ?
N1 C6 1.442(5) . ?
C6 C4 1.372(7) . ?
C6 C7 1.382(6) . ?
C3 C4 1.373(6) . ?
C12 C18 1.360(7) . ?
C12 C13 1.370(7) . ?
C17 C18 1.404(6) . ?
C8 C7 1.370(5) . ?
C10 C11 1.318(5) . ?
C4 C5 1.534(8) . ?
C13 C15 1.409(6) . ?
C13 C14 1.514(8) . ?
C9 Cu2 1.885(5) . ?
O3 Cu1 1.966(2) 6_666 ?
Cu2 Cl1 2.207(13) . ?

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
O2 Cu1 O3 90.13(11) 5_655 6_556 ?
O2 Cu1 O1 168.37(12) 5_655 . ?
O3 Cu1 O1 89.38(11) 6_556 . ?
O2 Cu1 O4 88.99(11) 5_655 2_654 ?
O3 Cu1 O4 168.20(12) 6_556 2_654 ?
O1 Cu1 O4 89.11(11) . 2_654 ?
O2 Cu1 O1W 97.63(12) 5_655 . ?
O3 Cu1 O1W 95.15(12) 6_556 . ?
O1 Cu1 O1W 93.98(12) . . ?
O4 Cu1 O1W 96.63(12) 2_654 . ?
O2 Cu1 Cu1 84.33(9) 5_655 5_655 ?
O3 Cu1 Cu1 83.64(9) 6_556 5_655 ?
O1 Cu1 Cu1 84.07(9) . 5_655 ?
O4 Cu1 Cu1 84.56(9) 2_654 5_655 ?
O1W Cu1 Cu1 177.71(8) . 5_655 ?
C19 O4 Cu1 122.3(2) . 2_655 ?
C1 O1 Cu1 122.9(2) . . ?
C1 O2 Cu1 122.6(3) . 5_655 ?
O4 C19 O3 126.3(3) . . ?
O4 C19 C16 117.2(4) . . ?
O3 C19 C16 116.4(4) . . ?
O1 C1 O2 126.0(3) . . ?
O1 C1 C2 116.8(4) . . ?
O2 C1 C2 117.2(4) . . ?
C8 C2 C3 119.5(4) . . ?
C8 C2 C1 120.6(4) . . ?
C3 C2 C1 119.9(4) . . ?
C9 N2 C11 109.8(3) . . ?
C9 N2 C12 124.6(3) . . ?
C11 N2 C12 125.6(3) . . ?
C17 C16 C15 119.8(4) . . ?
C17 C16 C19 120.4(4) . . ?
C15 C16 C19 119.8(4) . . ?
C9 N1 C10 109.6(3) . . ?
C9 N1 C6 124.2(3) . . ?
C10 N1 C6 126.2(3) . . ?
C4 C6 C7 121.7(4) . . ?
C4 C6 N1 118.9(4) . . ?
C7 C6 N1 119.4(5) . . ?
C4 C3 C2 120.8(5) . . ?
C18 C12 C13 122.4(4) . . ?
C18 C12 N2 117.4(4) . . ?
C13 C12 N2 120.2(5) . . ?
C16 C17 C18 119.3(5) . . ?
C7 C8 C2 119.7(4) . . ?
C11 C10 N1 107.7(4) . . ?
C10 C11 N2 107.4(3) . . ?
C8 C7 C6 119.8(5) . . ?
C3 C4 C6 118.4(5) . . ?
C3 C4 C5 120.6(6) . . ?
C6 C4 C5 121.0(4) . . ?
C12 C13 C15 116.5(5) . . ?
C12 C13 C14 122.4(5) . . ?
C15 C13 C14 121.1(5) . . ?
N2 C9 N1 105.5(4) . . ?
N2 C9 Cu2 129.2(3) . . ?
N1 C9 Cu2 123.2(3) . . ?
C16 C15 C13 122.0(5) . . ?
C12 C18 C17 119.9(4) . . ?
C19 O3 Cu1 123.1(3) . 6_666 ?
C9 Cu2 Cl1 179.1(4) . . ?

_refine_diff_density_max         0.774
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.066



