# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_mms3r
_database_code_depnum_ccdc_archive 'CCDC 969755'
loop_
_audit_author_name
_audit_author_address
'Professor Jim Simpson'
;Alzahra University
Iran
;
_audit_update_record             
;
2018-05-07 deposited with the CCDC.	2019-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97


_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 Cl2 Co N6, 2(H2O)'
_chemical_formula_sum            'C18 H16 Cl2 Co N6 O2'
_chemical_formula_weight         478.20

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.678(3)
_cell_length_b                   8.791(3)
_cell_length_c                   13.536(5)
_cell_angle_alpha                101.547(12)
_cell_angle_beta                 99.354(11)
_cell_angle_gamma                103.124(10)
_cell_volume                     961.6(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    94(2)
_cell_measurement_reflns_used    2013
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      21.17

_exptl_crystal_description       block
_exptl_crystal_colour            'dark green'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             486
_exptl_absorpt_coefficient_mu    1.199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5499
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2011)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      94(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6479
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_sigmaI/netI    0.0822
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         25.33
_reflns_number_total             2078
_reflns_number_gt                1557
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_molecular_graphics    
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material  
;
SHELXL-97, enCIFer (Allen et al., 2004), PLATON (Spek, 2009), 
PublCIF (Westrip 2010)
;

_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     
'calc w=1/[σ²(Fo²)+(0.0507P)²+24.0685P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2078
_refine_ls_number_parameters     284
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1336
_refine_ls_R_factor_gt           0.1046
_refine_ls_wR_factor_ref         0.2658
_refine_ls_wR_factor_gt          0.2536
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_restrained_S_all      1.175
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.4461(2) 0.9597(3) 0.14073(17) 0.0342(8) Uani 1 1 d . . .
Cl1 Cl 0.3506(15) 0.9005(13) 0.2833(6) 0.020(4) Uani 0.69(6) 1 d PU A 1
Cl1A Cl 0.399(6) 0.851(7) 0.284(2) 0.082(12) Uani 0.31(6) 1 d P A 2
Cl2 Cl 0.2750(5) 0.7891(5) -0.0036(3) 0.0401(12) Uani 1 1 d . A .
N1 N 0.6469(15) 1.1453(15) 0.2195(10) 0.033(3) Uani 1 1 d U A .
C1 C 0.7916(17) 1.1299(18) 0.2420(11) 0.026(4) Uani 1 1 d . . .
C2 C 0.7994(19) 0.963(2) 0.1982(13) 0.036(4) Uani 1 1 d . A .
C3 C 0.9415(18) 0.912(2) 0.2147(13) 0.035(4) Uani 1 1 d . . .
H3 H 1.0407 0.9842 0.2547 0.042 Uiso 1 1 calc R A .
C4 C 0.933(2) 0.756(2) 0.1720(13) 0.042(5) Uani 1 1 d . A .
H4 H 1.0269 0.7176 0.1821 0.050 Uiso 1 1 calc R . .
C5 C 0.787(2) 0.652(2) 0.1135(14) 0.047(5) Uani 1 1 d . . .
H5 H 0.7809 0.5435 0.0823 0.056 Uiso 1 1 calc R A .
C6 C 0.6453(18) 0.710(2) 0.1002(13) 0.033(4) Uani 1 1 d . A .
H6 H 0.5449 0.6390 0.0607 0.040 Uiso 1 1 calc R . .
N4 N 0.6539(14) 0.8636(16) 0.1431(10) 0.035(4) Uani 1 1 d . A .
C7 C 0.6291(18) 1.297(2) 0.2416(12) 0.033(4) Uani 1 1 d U . .
C8 C 0.4634(18) 1.3101(19) 0.2017(12) 0.034(4) Uani 1 1 d . A .
C9 C 0.4285(19) 1.454(2) 0.2218(12) 0.037(4) Uani 1 1 d U . .
H9 H 0.5073 1.5489 0.2626 0.044 Uiso 1 1 calc R A .
C10 C 0.270(2) 1.457(2) 0.1794(14) 0.050(5) Uani 1 1 d . A .
H10 H 0.2391 1.5547 0.1907 0.060 Uiso 1 1 calc R . .
C11 C 0.1598(18) 1.313(2) 0.1205(12) 0.037(4) Uani 1 1 d . . .
H11 H 0.0521 1.3125 0.0918 0.045 Uiso 1 1 calc R A .
C12 C 0.2075(19) 1.173(2) 0.1041(12) 0.036(4) Uani 1 1 d U A .
H12 H 0.1312 1.0762 0.0642 0.044 Uiso 1 1 calc R . .
N5 N 0.3609(13) 1.1698(15) 0.1435(10) 0.033(3) Uani 1 1 d . A .
N2 N 0.9225(14) 1.2455(14) 0.2902(10) 0.029(3) Uani 1 1 d . A .
N3 N 0.7536(13) 1.4249(14) 0.2909(9) 0.028(3) Uani 1 1 d . A .
C13 C 0.8936(18) 1.391(2) 0.3177(12) 0.031(4) Uani 1 1 d U . .
C14 C 1.0306(18) 1.5251(19) 0.3801(12) 0.031(4) Uani 1 1 d U A .
N6 N 1.1732(16) 1.4972(17) 0.4100(10) 0.043(4) Uani 1 1 d U . .
C15 C 1.299(2) 1.618(2) 0.4689(13) 0.045(5) Uani 1 1 d . A .
H15 H 1.4006 1.5973 0.4879 0.054 Uiso 1 1 calc R . .
C16 C 1.284(2) 1.769(2) 0.5021(13) 0.039(4) Uani 1 1 d U . .
H16 H 1.3742 1.8531 0.5442 0.047 Uiso 1 1 calc R A .
C17 C 1.1339(18) 1.800(2) 0.4731(12) 0.036(4) Uani 1 1 d U A .
H17 H 1.1212 1.9048 0.4959 0.044 Uiso 1 1 calc R . .
C18 C 1.0034(17) 1.6767(17) 0.4112(11) 0.024(4) Uani 1 1 d U . .
H18 H 0.9003 1.6945 0.3908 0.029 Uiso 1 1 calc R A .
O1W O 1.3104(14) 1.2248(18) 0.4140(11) 0.065(4) Uani 1 1 d D . .
H1W H 1.32(2) 1.154(18) 0.364(12) 0.098 Uiso 1 1 d D . .
H2W H 1.403(11) 1.292(18) 0.438(14) 0.098 Uiso 1 1 d D . .
O2W O 0.6814(19) 0.8161(16) 0.3865(10) 0.069(4) Uani 1 1 d D . .
H3W H 0.67(3) 0.908(12) 0.409(13) 0.103 Uiso 1 1 d D . .
H4W H 0.73(3) 0.79(2) 0.439(9) 0.103 Uiso 1 1 d 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
Co1 N1 2.060(13) . ?
Co1 N5 2.136(12) . ?
Co1 N4 2.156(13) . ?
Co1 Cl2 2.268(4) . ?
Co1 Cl1 2.325(9) . ?
Co1 Cl1A 2.38(4) . ?
N1 C1 1.287(17) . ?
N1 C7 1.35(2) . ?
C1 N2 1.311(18) . ?
C1 C2 1.49(2) . ?
C2 N4 1.358(19) . ?
C2 C3 1.41(2) . ?
C3 C4 1.36(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.39(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.43(2) . ?
C5 H5 0.9500 . ?
C6 N4 1.34(2) . ?
C6 H6 0.9500 . ?
C7 N3 1.340(18) . ?
C7 C8 1.49(2) . ?
C8 N5 1.349(19) . ?
C8 C9 1.35(2) . ?
C9 C10 1.41(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.39(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.37(2) . ?
C11 H11 0.9500 . ?
C12 N5 1.361(19) . ?
C12 H12 0.9500 . ?
N2 C13 1.35(2) . ?
N3 C13 1.327(18) . ?
C13 C14 1.47(2) . ?
C14 N6 1.331(19) . ?
C14 C18 1.40(2) . ?
N6 C15 1.34(2) . ?
C15 C16 1.36(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.40(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.39(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
O1W H1W 0.85(2) . ?
O1W H2W 0.85(2) . ?
O2W H3W 0.85(2) . ?
O2W H4W 0.85(2) . ?

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
N1 Co1 N5 76.6(5) . . ?
N1 Co1 N4 72.8(5) . . ?
N5 Co1 N4 145.7(5) . . ?
N1 Co1 Cl2 154.2(4) . . ?
N5 Co1 Cl2 100.3(3) . . ?
N4 Co1 Cl2 100.4(4) . . ?
N1 Co1 Cl1 97.8(4) . . ?
N5 Co1 Cl1 95.6(5) . . ?
N4 Co1 Cl1 103.5(5) . . ?
Cl2 Co1 Cl1 108.1(3) . . ?
N1 Co1 Cl1A 96.8(7) . . ?
N5 Co1 Cl1A 111(2) . . ?
N4 Co1 Cl1A 88(2) . . ?
Cl2 Co1 Cl1A 107.9(6) . . ?
Cl1 Co1 Cl1A 16.3(17) . . ?
C1 N1 C7 117.1(13) . . ?
C1 N1 Co1 124.6(11) . . ?
C7 N1 Co1 118.0(10) . . ?
N1 C1 N2 126.3(14) . . ?
N1 C1 C2 111.9(13) . . ?
N2 C1 C2 121.6(13) . . ?
N4 C2 C3 123.4(15) . . ?
N4 C2 C1 113.1(13) . . ?
C3 C2 C1 123.5(15) . . ?
C4 C3 C2 118.1(15) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 119.9(16) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 119.7(16) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
N4 C6 C5 120.3(14) . . ?
N4 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 N4 C2 118.6(13) . . ?
C6 N4 Co1 123.9(10) . . ?
C2 N4 Co1 117.3(11) . . ?
N3 C7 N1 122.1(13) . . ?
N3 C7 C8 122.9(14) . . ?
N1 C7 C8 114.9(13) . . ?
N5 C8 C9 125.8(14) . . ?
N5 C8 C7 113.5(13) . . ?
C9 C8 C7 120.6(14) . . ?
C8 C9 C10 117.0(16) . . ?
C8 C9 H9 121.5 . . ?
C10 C9 H9 121.5 . . ?
C11 C10 C9 118.8(16) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C12 C11 C10 119.7(15) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
N5 C12 C11 121.9(15) . . ?
N5 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C8 N5 C12 116.7(13) . . ?
C8 N5 Co1 116.2(9) . . ?
C12 N5 Co1 126.4(11) . . ?
C1 N2 C13 113.3(12) . . ?
C13 N3 C7 114.8(13) . . ?
N3 C13 N2 125.8(13) . . ?
N3 C13 C14 117.0(14) . . ?
N2 C13 C14 117.2(14) . . ?
N6 C14 C18 122.2(14) . . ?
N6 C14 C13 119.4(15) . . ?
C18 C14 C13 118.3(14) . . ?
C14 N6 C15 119.9(15) . . ?
N6 C15 C16 122.1(16) . . ?
N6 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C15 C16 C17 118.7(16) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C18 C17 C16 120.1(15) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C14 117.0(14) . . ?
C17 C18 H18 121.5 . . ?
C14 C18 H18 121.5 . . ?
H1W O1W H2W 106(4) . . ?
H3W O2W H4W 106(4) . . ?

_diffrn_measured_fraction_theta_max 0.590
_diffrn_reflns_theta_full        25.33
_diffrn_measured_fraction_theta_full 0.590
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.965
_refine_diff_density_rms         0.143

