# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_mo_C20SB15_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1036962'
_audit_update_record             
;
2014-12-01 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H8 Cl Cu2 N4 O3'
_chemical_formula_sum            'C8 H8 Cl Cu2 N4 O3'
_chemical_formula_weight         370.71

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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.5078(7)
_cell_length_b                   9.1266(6)
_cell_length_c                   11.7875(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.869(3)
_cell_angle_gamma                90
_cell_volume                     1113.70(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9567
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      38.70

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.211
_exptl_crystal_F_000             732
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_min          0.145
_exptl_absorpt_coefficient_mu    4.062
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5316
_exptl_absorpt_correction_T_max  0.7485
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13166
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.839
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2283
_reflns_number_gt                2121
_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.
 
 _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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0288P)²+0.9391P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2283
_refine_ls_number_parameters     163
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0208
_refine_ls_wR_factor_ref         0.0559
_refine_ls_wR_factor_gt          0.0545
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_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 0.78027(2) 0.72579(3) 0.44131(2) 0.01559(8) Uani 1 1 d . U . . .
Cu2 Cu 0.63017(3) 0.62819(3) 0.17821(2) 0.01733(9) Uani 1 1 d . U . . .
Cl1 Cl 0.85505(5) 0.88747(5) 0.58187(4) 0.02105(12) Uani 1 1 d . U . . .
O1 O 0.71650(15) 0.57374(15) 0.33045(12) 0.0195(3) Uani 1 1 d . U . . .
O2 O 0.59293(15) 0.42632(15) 0.12380(12) 0.0193(3) Uani 1 1 d . U . . .
O3 O 0.47758(15) 0.31381(16) -0.02837(12) 0.0206(3) Uani 1 1 d . U . . .
N1 N 0.64127(17) 0.83043(19) 0.22544(14) 0.0167(3) Uani 1 1 d . U . . .
N2 N 0.70949(17) 0.87222(18) 0.32907(15) 0.0177(4) Uani 1 1 d . U . . .
N3 N 0.84438(17) 0.55525(19) 0.53232(15) 0.0181(4) Uani 1 1 d . U . . .
N4 N 0.82086(18) 0.42629(19) 0.47708(15) 0.0197(4) Uani 1 1 d . U . . .
C1 C 0.5954(2) 0.9505(2) 0.16782(17) 0.0187(4) Uani 1 1 d . U . . .
H1 H 0.5446 0.9511 0.0929 0.022 Uiso 1 1 calc R U . . .
C2 C 0.6327(2) 1.0743(2) 0.23319(19) 0.0226(4) Uani 1 1 d . U . . .
H2 H 0.6137 1.1738 0.2137 0.027 Uiso 1 1 calc R U . . .
C3 C 0.7044(2) 1.0190(2) 0.33369(19) 0.0232(5) Uani 1 1 d . U . . .
H3 H 0.7442 1.0768 0.3969 0.028 Uiso 1 1 calc R U . . .
C4 C 0.9117(2) 0.5237(2) 0.63629(18) 0.0215(4) Uani 1 1 d . U . . .
H4 H 0.9414 0.5938 0.6945 0.026 Uiso 1 1 calc R U . . .
C5 C 0.9320(2) 0.3735(2) 0.64682(19) 0.0251(5) Uani 1 1 d . U . . .
H5 H 0.9771 0.3221 0.7116 0.030 Uiso 1 1 calc R U . . .
C6 C 0.8729(2) 0.3150(2) 0.5436(2) 0.0268(5) Uani 1 1 d . U . . .
H6 H 0.8696 0.2142 0.5232 0.032 Uiso 1 1 calc R U . . .
C7 C 0.7494(2) 0.4297(2) 0.35729(18) 0.0207(4) Uani 1 1 d . U . . .
H7A H 0.8042 0.3908 0.3038 0.025 Uiso 1 1 calc R U . . .
H7B H 0.6706 0.3685 0.3506 0.025 Uiso 1 1 calc R U . . .
C8 C 0.5203(2) 0.4251(2) 0.02767(17) 0.0180(4) Uani 1 1 d . U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.02164(15) 0.01305(14) 0.00977(13) -0.00087(9) -0.00385(10) -0.00130(9)
Cu2 0.02741(16) 0.01121(13) 0.00977(13) -0.00070(9) -0.00699(10) -0.00088(9)
Cl1 0.0285(3) 0.0173(2) 0.0140(2) -0.00316(18) -0.00576(19) -0.00217(19)
O1 0.0301(8) 0.0118(7) 0.0126(7) -0.0009(5) -0.0076(6) -0.0005(6)
O2 0.0289(8) 0.0137(7) 0.0115(7) 0.0002(5) -0.0076(6) -0.0010(6)
O3 0.0325(8) 0.0123(7) 0.0131(7) -0.0013(6) -0.0075(6) -0.0011(6)
N1 0.0215(9) 0.0148(8) 0.0118(8) -0.0017(6) -0.0030(6) -0.0009(7)
N2 0.0246(9) 0.0147(8) 0.0112(8) -0.0025(6) -0.0037(7) -0.0022(7)
N3 0.0243(9) 0.0145(8) 0.0136(8) -0.0020(6) -0.0025(7) -0.0012(7)
N4 0.0240(9) 0.0160(8) 0.0156(8) -0.0011(7) -0.0066(7) -0.0007(7)
C1 0.0235(10) 0.0173(10) 0.0134(9) 0.0010(8) -0.0019(8) -0.0003(8)
C2 0.0331(12) 0.0140(10) 0.0190(10) -0.0005(8) -0.0001(9) -0.0001(9)
C3 0.0353(13) 0.0138(10) 0.0179(10) -0.0026(8) -0.0029(9) -0.0031(9)
C4 0.0255(11) 0.0231(11) 0.0131(9) -0.0006(8) -0.0046(8) -0.0017(9)
C5 0.0295(12) 0.0238(11) 0.0179(10) 0.0063(9) -0.0073(9) 0.0009(9)
C6 0.0346(13) 0.0162(10) 0.0247(11) 0.0027(9) -0.0087(10) 0.0002(9)
C7 0.0285(11) 0.0161(10) 0.0137(10) -0.0017(8) -0.0070(8) 0.0014(8)
C8 0.0248(11) 0.0138(10) 0.0135(9) 0.0017(8) -0.0018(8) 0.0003(8)

_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 N2 1.9371(17) . ?
Cu1 N3 1.9441(18) . ?
Cu1 O1 1.9448(14) . ?
Cu1 Cl1 2.2569(5) . ?
Cu2 N1 1.9257(17) . ?
Cu2 O1 1.9318(14) . ?
Cu2 O2 1.9679(14) . ?
Cu2 O3 1.9991(14) 3_665 ?
O1 C7 1.382(2) . ?
O2 C8 1.253(3) . ?
O3 C8 1.252(3) . ?
O3 Cu2 1.9991(14) 3_665 ?
N1 C1 1.335(3) . ?
N1 N2 1.361(2) . ?
N2 C3 1.342(3) . ?
N3 C4 1.337(3) . ?
N3 N4 1.347(2) . ?
N4 C6 1.341(3) . ?
N4 C7 1.482(3) . ?
C1 C2 1.386(3) . ?
C2 C3 1.385(3) . ?
C4 C5 1.390(3) . ?
C5 C6 1.375(3) . ?
C8 C8 1.543(4) 3_665 ?

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
N2 Cu1 N3 170.20(7) . . ?
N2 Cu1 O1 89.18(7) . . ?
N3 Cu1 O1 81.17(7) . . ?
N2 Cu1 Cl1 95.45(5) . . ?
N3 Cu1 Cl1 94.26(5) . . ?
O1 Cu1 Cl1 175.08(5) . . ?
N1 Cu2 O1 89.00(7) . . ?
N1 Cu2 O2 172.05(7) . . ?
O1 Cu2 O2 95.59(6) . . ?
N1 Cu2 O3 89.92(7) . 3_665 ?
O1 Cu2 O3 173.46(7) . 3_665 ?
O2 Cu2 O3 84.78(6) . 3_665 ?
C7 O1 Cu2 121.09(12) . . ?
C7 O1 Cu1 118.76(12) . . ?
Cu2 O1 Cu1 119.57(7) . . ?
C8 O2 Cu2 111.05(13) . . ?
C8 O3 Cu2 110.41(13) . 3_665 ?
C1 N1 N2 108.37(16) . . ?
C1 N1 Cu2 129.88(14) . . ?
N2 N1 Cu2 121.65(13) . . ?
C3 N2 N1 107.31(17) . . ?
C3 N2 Cu1 132.40(15) . . ?
N1 N2 Cu1 120.09(13) . . ?
C4 N3 N4 106.22(17) . . ?
C4 N3 Cu1 139.19(15) . . ?
N4 N3 Cu1 114.53(13) . . ?
C6 N4 N3 110.86(17) . . ?
C6 N4 C7 131.48(18) . . ?
N3 N4 C7 117.62(16) . . ?
N1 C1 C2 110.08(18) . . ?
C3 C2 C1 103.84(18) . . ?
N2 C3 C2 110.40(19) . . ?
N3 C4 C5 110.07(19) . . ?
C6 C5 C4 105.4(2) . . ?
N4 C6 C5 107.5(2) . . ?
O1 C7 N4 107.69(16) . . ?
O3 C8 O2 126.28(19) . . ?
O3 C8 C8 116.6(2) . 3_665 ?
O2 C8 C8 117.1(2) . 3_665 ?

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.081


#===END
