# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_Co-metf1
_database_code_depnum_ccdc_archive 'CCDC 1998783'
loop_
_audit_author_name
_audit_author_address
'Richard DVries'
;Universidad Santiago de Cali
Colombia
;
_audit_update_record             
;
2020-04-23 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_audit_creation_date             2019-07-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H33 Co N15, 2(Cl), H2 O'
_chemical_formula_sum            'C12 H35 Cl2 Co N15 O'
_chemical_formula_weight         535.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H36 N15 O6 Cl3 Co1 '
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'
Co Co 0.3494 0.9721 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   36.470(2)
_cell_length_b                   8.5892(6)
_cell_length_c                   17.3656(13)
_cell_angle_alpha                90
_cell_angle_beta                 99.376(6)
_cell_angle_gamma                90
_cell_volume                     5367.1(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6557
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.9620
_cell_measurement_theta_min      2.6460
_shelx_estimated_absorpt_T_max   0.780
_shelx_estimated_absorpt_T_min   0.722
_exptl_absorpt_coefficient_mu    0.872
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light red'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2248
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
8 -12 4 0.0065
3 2 -24 0.0672
-10 12 2 0.0506
-36 8 8 0.0467
-36 8 -3 0.0033
-28 6 -14 0.0409

_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
8.2754 -11.6791 4.3374 -0.4067 0.9135 -0.0000
3.4734 2.4481 -23.8523 0.1578 -0.3545 -0.9216
-9.8648 11.8674 2.0069 0.3930 -0.8827 0.2577
-35.9412 8.3155 7.5904 0.7863 -0.4540 0.4191
-36.2370 8.1147 -2.7420 0.8660 -0.5000 0.0000
-28.3392 6.0411 -13.9256 0.7603 -0.4389 -0.4789

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1201
_diffrn_reflns_av_unetI/netI     0.0956
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            38196
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_min         2.672
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 118.00   1.00  275.00    --   27.63  54.00-180.00  187
  2  ω    -69.00 118.00   1.00  275.00    --   27.63  54.00-150.00  187
  3  ω    -69.00 118.00   1.00  275.00    --   27.63  54.00  30.00  187
  4  ω    -69.00 113.00   1.00  275.00    --   27.63  54.00 120.00  182
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0192036000
_diffrn_orient_matrix_UB_12      0.0184253000
_diffrn_orient_matrix_UB_13      -0.0075226000
_diffrn_orient_matrix_UB_21      -0.0043651000
_diffrn_orient_matrix_UB_22      -0.0790428000
_diffrn_orient_matrix_UB_23      0.0061144000
_diffrn_orient_matrix_UB_31      0.0003586000
_diffrn_orient_matrix_UB_32      0.0152028000
_diffrn_orient_matrix_UB_33      0.0402518000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3740
_reflns_number_total             6485
_reflns_odcompleteness_completeness 99.85
_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.
 
 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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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         0.524
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         6485
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0601
_refine_ls_restrained_S_all      1.009
_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)+(0.0581P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1598
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Rotating group:
 N2(H2A,H2B), N12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N8(H8), N13(H13)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C7(H7C,H7D,H7E), C8(H8A,H8B,H8C), C4(H4A,H4B,H4C), C12(H12C,
 H12D,H12E), C11(H11A,H11B,H11C)
;
_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
Co01 Co 0.64718(2) 0.53306(6) 0.33437(3) 0.03345(15) Uani 1 1 d . . . . .
Cl1 Cl 0.66033(3) 0.76839(13) 0.62616(7) 0.0626(3) Uani 1 1 d . . . . .
Cl2 Cl 0.70026(3) 0.05600(15) 0.41814(7) 0.0670(3) Uani 1 1 d . . . . .
N6 N 0.67132(8) 0.5654(4) 0.43840(18) 0.0372(7) Uani 1 1 d . . . . .
N11 N 0.66187(9) 0.7362(4) 0.30773(19) 0.0392(7) Uani 1 1 d . . . . .
N10 N 0.69195(9) 0.4389(4) 0.3124(2) 0.0406(8) Uani 1 1 d . . . . .
N1 N 0.62913(9) 0.3333(4) 0.35948(19) 0.0402(7) Uani 1 1 d . . . . .
N5 N 0.60245(8) 0.6183(4) 0.35979(18) 0.0370(7) Uani 1 1 d . . . . .
N9 N 0.75281(8) 0.3475(4) 0.33098(18) 0.0444(8) Uani 1 1 d . . . . .
N3 N 0.56681(8) 0.3988(3) 0.33378(19) 0.0417(7) Uani 1 1 d . . . . .
H3 H 0.545645 0.364701 0.310850 0.050 Uiso 1 1 calc R . . . .
N4 N 0.53851(8) 0.6349(4) 0.3484(2) 0.0481(8) Uani 1 1 d . . . . .
N8 N 0.73063(9) 0.4811(4) 0.42872(18) 0.0479(8) Uani 1 1 d . . . . .
H8 H 0.753163 0.475719 0.452724 0.057 Uiso 1 1 calc R . . . .
N15 N 0.62452(9) 0.5080(4) 0.22815(19) 0.0437(8) Uani 1 1 d . . . . .
O1 O 0.62758(9) -0.0926(4) 0.4592(2) 0.0701(9) Uani 1 1 d . . . . .
H1A H 0.648625 -0.053722 0.455112 0.105 Uiso 1 1 d G . . . .
H1B H 0.630708 -0.132760 0.504654 0.105 Uiso 1 1 d G . . . .
N13 N 0.61709(10) 0.7690(4) 0.1984(2) 0.0542(9) Uani 1 1 d . . . . .
H13 H 0.602554 0.835042 0.171471 0.065 Uiso 1 1 calc R . . . .
C6 C 0.72393(9) 0.4204(4) 0.3548(2) 0.0348(8) Uani 1 1 d . . . . .
C2 C 0.57029(9) 0.5531(4) 0.3483(2) 0.0337(8) Uani 1 1 d . . . . .
C5 C 0.70548(10) 0.5495(4) 0.4687(2) 0.0396(9) Uani 1 1 d . . . . .
N2 N 0.58264(10) 0.1477(4) 0.3628(2) 0.0633(11) Uani 1 1 d . . . . .
H2A H 0.599979 0.096571 0.392621 0.076 Uiso 1 1 d GR . . . .
H2B H 0.563069 0.150850 0.385357 0.076 Uiso 1 1 d GR . . . .
C1 C 0.59497(10) 0.2934(4) 0.3534(2) 0.0402(9) Uani 1 1 d . . . . .
N12 N 0.64889(11) 0.9808(4) 0.2552(2) 0.0633(10) Uani 1 1 d . . . . .
H12A H 0.635080 1.022673 0.214935 0.076 Uiso 1 1 d GR . . . .
H12B H 0.642935 1.022010 0.297114 0.076 Uiso 1 1 d GR . . . .
C9 C 0.64356(11) 0.8265(5) 0.2560(2) 0.0454(9) Uani 1 1 d . . . . .
N14 N 0.59092(11) 0.5849(5) 0.1090(2) 0.0693(11) Uani 1 1 d . . . . .
N7 N 0.71968(13) 0.5948(6) 0.5409(2) 0.0743(15) Uani 1 1 d . . . . .
C10 C 0.61177(11) 0.6143(6) 0.1798(2) 0.0484(10) Uani 1 1 d . . . . .
C3 C 0.50500(11) 0.5648(5) 0.3668(3) 0.0647(13) Uani 1 1 d . . . . .
H3A H 0.487231 0.553322 0.319908 0.097 Uiso 1 1 calc GR . . . .
H3B H 0.494783 0.630125 0.402876 0.097 Uiso 1 1 calc GR . . . .
H3C H 0.510722 0.464374 0.389951 0.097 Uiso 1 1 calc GR . . . .
C7 C 0.78750(11) 0.3180(6) 0.3816(3) 0.0676(13) Uani 1 1 d . . . . .
H7C H 0.800480 0.414451 0.393567 0.101 Uiso 1 1 calc GR . . . .
H7D H 0.802435 0.249291 0.356028 0.101 Uiso 1 1 calc GR . . . .
H7E H 0.782689 0.270597 0.429049 0.101 Uiso 1 1 calc GR . . . .
C8 C 0.74821(13) 0.2800(6) 0.2540(3) 0.0761(16) Uani 1 1 d . . . . .
H8A H 0.729351 0.201083 0.249524 0.114 Uiso 1 1 calc GR . . . .
H8B H 0.771263 0.234489 0.245572 0.114 Uiso 1 1 calc GR . . . .
H8C H 0.740960 0.359594 0.215758 0.114 Uiso 1 1 calc GR . . . .
C4 C 0.53962(13) 0.8038(5) 0.3499(3) 0.0731(15) Uani 1 1 d . . . . .
H4A H 0.548490 0.838763 0.402084 0.110 Uiso 1 1 calc GR . . . .
H4B H 0.515097 0.844149 0.332738 0.110 Uiso 1 1 calc GR . . . .
H4C H 0.556005 0.840242 0.315736 0.110 Uiso 1 1 calc GR . . . .
C12 C 0.57610(14) 0.4296(7) 0.0909(3) 0.091(2) Uani 1 1 d . . . . .
H12C H 0.594996 0.365018 0.074952 0.137 Uiso 1 1 calc GR . . . .
H12D H 0.555252 0.435751 0.049373 0.137 Uiso 1 1 calc GR . . . .
H12E H 0.568250 0.385581 0.136333 0.137 Uiso 1 1 calc GR . . . .
C11 C 0.5941(2) 0.6857(9) 0.0423(3) 0.128(3) Uani 1 1 d . . . . .
H11A H 0.571368 0.742592 0.027736 0.192 Uiso 1 1 calc GR . . . .
H11B H 0.598736 0.623130 -0.000877 0.192 Uiso 1 1 calc GR . . . .
H11C H 0.614261 0.757407 0.056432 0.192 Uiso 1 1 calc GR . . . .
H5 H 0.6037(8) 0.702(3) 0.3760(16) 0.007(8) Uiso 1 1 d . . . . .
H11 H 0.6788(10) 0.781(4) 0.342(2) 0.039(11) Uiso 1 1 d . . . . .
H6 H 0.6588(11) 0.613(4) 0.468(2) 0.049(12) Uiso 1 1 d . . . . .
H1 H 0.6477(12) 0.265(5) 0.378(2) 0.064(14) Uiso 1 1 d . . . . .
H15 H 0.6232(13) 0.413(5) 0.211(3) 0.074(16) Uiso 1 1 d . . . . .
H10 H 0.6894(9) 0.396(4) 0.2787(18) 0.015(9) Uiso 1 1 d . . . . .
H7A H 0.7077(14) 0.636(6) 0.567(3) 0.073(17) Uiso 1 1 d . . . . .
H7B H 0.7398(12) 0.570(5) 0.558(2) 0.052(14) Uiso 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
Co01 N6 1.897(3) . ?
Co01 N11 1.904(3) . ?
Co01 N10 1.916(3) . ?
Co01 N1 1.913(3) . ?
Co01 N5 1.904(3) . ?
Co01 N15 1.906(3) . ?
N6 C5 1.278(5) . ?
N6 H6 0.85(4) . ?
N11 C9 1.288(5) . ?
N11 H11 0.87(4) . ?
N10 C6 1.284(5) . ?
N10 H10 0.68(3) . ?
N1 C1 1.280(5) . ?
N1 H1 0.91(4) . ?
N5 C2 1.286(4) . ?
N5 H5 0.77(3) . ?
N9 C6 1.347(4) . ?
N9 C7 1.441(5) . ?
N9 C8 1.441(5) . ?
N3 H3 0.8600 . ?
N3 C2 1.351(4) . ?
N3 C1 1.370(4) . ?
N4 C2 1.356(4) . ?
N4 C3 1.444(5) . ?
N4 C4 1.452(5) . ?
N8 H8 0.8600 . ?
N8 C6 1.371(4) . ?
N8 C5 1.369(4) . ?
N15 C10 1.276(5) . ?
N15 H15 0.87(5) . ?
O1 H1A 0.8505 . ?
O1 H1B 0.8519 . ?
N13 H13 0.8600 . ?
N13 C9 1.365(5) . ?
N13 C10 1.374(5) . ?
C5 N7 1.334(5) . ?
N2 H2A 0.8689 . ?
N2 H2B 0.8690 . ?
N2 C1 1.348(5) . ?
N12 H12A 0.8697 . ?
N12 H12B 0.8688 . ?
N12 C9 1.340(5) . ?
N14 C10 1.360(5) . ?
N14 C12 1.454(7) . ?
N14 C11 1.466(7) . ?
N7 H7A 0.76(5) . ?
N7 H7B 0.77(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C7 H7C 0.9600 . ?
C7 H7D 0.9600 . ?
C7 H7E 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C12 H12C 0.9600 . ?
C12 H12D 0.9600 . ?
C12 H12E 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
N6 Co01 N11 89.53(14) . . ?
N6 Co01 N10 88.48(14) . . ?
N6 Co01 N1 92.17(13) . . ?
N6 Co01 N5 90.29(13) . . ?
N6 Co01 N15 177.16(14) . . ?
N11 Co01 N10 93.20(14) . . ?
N11 Co01 N1 176.27(14) . . ?
N11 Co01 N5 89.40(13) . . ?
N11 Co01 N15 87.89(15) . . ?
N1 Co01 N10 90.17(14) . . ?
N5 Co01 N10 177.12(14) . . ?
N5 Co01 N1 87.27(13) . . ?
N5 Co01 N15 90.86(14) . . ?
N15 Co01 N10 90.49(14) . . ?
N15 Co01 N1 90.48(15) . . ?
Co01 N6 H6 116(3) . . ?
C5 N6 Co01 130.2(3) . . ?
C5 N6 H6 113(3) . . ?
Co01 N11 H11 115(2) . . ?
C9 N11 Co01 125.9(3) . . ?
C9 N11 H11 116(2) . . ?
Co01 N10 H10 113(3) . . ?
C6 N10 Co01 131.4(3) . . ?
C6 N10 H10 114(3) . . ?
Co01 N1 H1 113(3) . . ?
C1 N1 Co01 126.0(3) . . ?
C1 N1 H1 121(3) . . ?
Co01 N5 H5 116(2) . . ?
C2 N5 Co01 126.2(3) . . ?
C2 N5 H5 117(2) . . ?
C6 N9 C7 123.2(3) . . ?
C6 N9 C8 119.5(3) . . ?
C7 N9 C8 117.0(3) . . ?
C2 N3 H3 118.0 . . ?
C2 N3 C1 123.9(3) . . ?
C1 N3 H3 118.0 . . ?
C2 N4 C3 122.6(3) . . ?
C2 N4 C4 119.8(3) . . ?
C3 N4 C4 115.8(3) . . ?
C6 N8 H8 116.3 . . ?
C5 N8 H8 116.3 . . ?
C5 N8 C6 127.3(3) . . ?
Co01 N15 H15 115(3) . . ?
C10 N15 Co01 127.6(3) . . ?
C10 N15 H15 117(3) . . ?
H1A O1 H1B 104.5 . . ?
C9 N13 H13 117.3 . . ?
C9 N13 C10 125.3(4) . . ?
C10 N13 H13 117.3 . . ?
N10 C6 N9 124.3(3) . . ?
N10 C6 N8 119.8(3) . . ?
N9 C6 N8 115.8(3) . . ?
N5 C2 N3 120.8(3) . . ?
N5 C2 N4 122.2(3) . . ?
N3 C2 N4 117.0(3) . . ?
N6 C5 N8 121.7(3) . . ?
N6 C5 N7 123.9(4) . . ?
N7 C5 N8 114.3(4) . . ?
H2A N2 H2B 108.5 . . ?
C1 N2 H2A 108.5 . . ?
C1 N2 H2B 109.9 . . ?
N1 C1 N3 121.6(3) . . ?
N1 C1 N2 125.3(4) . . ?
N2 C1 N3 113.1(3) . . ?
H12A N12 H12B 108.3 . . ?
C9 N12 H12A 110.6 . . ?
C9 N12 H12B 109.7 . . ?
N11 C9 N13 121.2(4) . . ?
N11 C9 N12 122.9(4) . . ?
N12 C9 N13 115.9(4) . . ?
C10 N14 C12 120.0(4) . . ?
C10 N14 C11 120.0(5) . . ?
C12 N14 C11 116.4(5) . . ?
C5 N7 H7A 121(4) . . ?
C5 N7 H7B 118(3) . . ?
H7A N7 H7B 120(5) . . ?
N15 C10 N13 121.0(4) . . ?
N15 C10 N14 123.5(4) . . ?
N14 C10 N13 115.4(4) . . ?
N4 C3 H3A 109.5 . . ?
N4 C3 H3B 109.5 . . ?
N4 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N9 C7 H7C 109.5 . . ?
N9 C7 H7D 109.5 . . ?
N9 C7 H7E 109.5 . . ?
H7C C7 H7D 109.5 . . ?
H7C C7 H7E 109.5 . . ?
H7D C7 H7E 109.5 . . ?
N9 C8 H8A 109.5 . . ?
N9 C8 H8B 109.5 . . ?
N9 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
N4 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N14 C12 H12C 109.5 . . ?
N14 C12 H12D 109.5 . . ?
N14 C12 H12E 109.5 . . ?
H12C C12 H12D 109.5 . . ?
H12C C12 H12E 109.5 . . ?
H12D C12 H12E 109.5 . . ?
N14 C11 H11A 109.5 . . ?
N14 C11 H11B 109.5 . . ?
N14 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 -0.985 384.4 121.4 H2O
2 0.500 0.000 0.517 384.4 121.4 H2O

_olex2_date_sample_data_collection 2019-01-11
_olex2_submission_original_sample_id MFnCo1
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.402
_oxdiff_exptl_absorpt_empirical_full_min 0.907
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_Ni_metf1
_database_code_depnum_ccdc_archive 'CCDC 1998785'
loop_
_audit_author_name
_audit_author_address
'Richard DVries'
;Universidad Santiago de Cali
Colombia
;
_audit_update_record             
;
2020-04-23 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_audit_creation_date             2019-06-27
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C8 H21 N10 Ni), 2(Cl), 2(H2 O)'
_chemical_formula_sum            'C16 H46 Cl2 N20 Ni2 O2'
_chemical_formula_weight         739.05
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Ni N15 C12 H33 Cl2'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.3863(6)
_cell_length_b                   14.8373(9)
_cell_length_c                   15.7512(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.757(5)
_cell_angle_gamma                90
_cell_volume                     3025.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4052
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      34.5560
_cell_measurement_theta_min      2.7290
_shelx_estimated_absorpt_T_max   0.757
_shelx_estimated_absorpt_T_min   0.649
_exptl_absorpt_coefficient_mu    1.476
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light orange'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1552
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14764
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         2.674
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00 118.00   1.00   19.50    --   27.63  54.00 -30.00  182
  2  ω     23.00  59.00   1.00   19.50    --   27.63  54.00-150.00   36
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0103124000
_diffrn_orient_matrix_UB_12      -0.0346910000
_diffrn_orient_matrix_UB_13      0.0276652000
_diffrn_orient_matrix_UB_21      -0.0293701000
_diffrn_orient_matrix_UB_22      -0.0233867000
_diffrn_orient_matrix_UB_23      -0.0373201000
_diffrn_orient_matrix_UB_31      0.0451505000
_diffrn_orient_matrix_UB_32      -0.0230211000
_diffrn_orient_matrix_UB_33      -0.0035044000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4991
_reflns_number_total             8724
_reflns_odcompleteness_completeness 99.83
_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 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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         0.715
_refine_diff_density_min         -0.654
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         8724
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.133
_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)+(0.0340P)²+2.5740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1444
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B), O2(H2C,H2D)
2.b Rotating group:
 N2(H2A,H2B), N17(H17A,H17B), N12(H12A,H12B)
2.c X=CH2 refined with riding coordinates:
 N7(H7A,H7B)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C12(H12C,H12D,H12E), C4(H4A,H4B,H4C), C15(H15A,H15B,H15C),
 C3(H3A,H3B,H3C), C7(H7C,H7D,H7E), C16(H16A,H16B,H16C), C11(H11A,H11B,H11C)
;
_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
Ni1 Ni 0.73747(3) 0.62393(3) 0.00262(3) 0.02863(12) Uani 1 1 d . . . . .
Ni2 Ni 0.23661(3) 0.62505(3) 0.50323(3) 0.02885(12) Uani 1 1 d . . . . .
Cl1 Cl 0.97628(7) 0.96361(7) -0.23863(7) 0.0492(3) Uani 1 1 d . . . . .
Cl2 Cl 0.51180(7) 0.29138(8) 0.24972(6) 0.0489(3) Uani 1 1 d . . . . .
N18 N 0.0865(2) 0.6722(2) 0.6278(2) 0.0352(7) Uani 1 1 d . . . . .
N3 N 0.89704(19) 0.6691(2) -0.11970(19) 0.0326(7) Uani 1 1 d . . . . .
N1 N 0.7232(2) 0.6584(2) -0.1120(2) 0.0377(8) Uani 1 1 d . . . . .
N5 N 0.8785(2) 0.6223(2) 0.0190(2) 0.0331(7) Uani 1 1 d . . . . .
N8 N 0.5808(2) 0.5801(2) 0.1224(2) 0.0348(7) Uani 1 1 d . . . . .
N16 N 0.2557(2) 0.6630(2) 0.6184(2) 0.0390(8) Uani 1 1 d . . . . .
N15 N 0.3775(2) 0.6266(2) 0.5161(2) 0.0332(7) Uani 1 1 d . . . . .
O1 O 1.0023(2) 0.7561(2) -0.2382(2) 0.0531(8) Uani 1 1 d . . . . .
H1A H 0.972539 0.733571 -0.201473 0.080 Uiso 1 1 d G . . . .
H1B H 0.993713 0.812639 -0.234675 0.080 Uiso 1 1 d G . . . .
N6 N 0.7529(2) 0.5881(2) 0.1181(2) 0.0384(7) Uani 1 1 d . . . . .
N4 N 1.0367(2) 0.6199(2) -0.0135(2) 0.0393(8) Uani 1 1 d . . . . .
N11 N 0.2180(2) 0.5891(2) 0.3888(2) 0.0394(8) Uani 1 1 d . . . . .
N13 N 0.3904(2) 0.5800(2) 0.37567(19) 0.0349(7) Uani 1 1 d . . . . .
O2 O 0.4903(3) 0.4993(2) 0.2511(2) 0.0567(8) Uani 1 1 d . . . . .
H2C H 0.489278 0.442051 0.251449 0.085 Uiso 1 1 d G . . . .
H2D H 0.468466 0.514570 0.295209 0.085 Uiso 1 1 d G . . . .
N9 N 0.4358(2) 0.6271(2) 0.0202(2) 0.0383(7) Uani 1 1 d . . . . .
N10 N 0.5944(2) 0.6271(2) -0.0138(2) 0.0349(7) Uani 1 1 d . . . . .
N19 N -0.0624(2) 0.6248(2) 0.5291(2) 0.0392(7) Uani 1 1 d . . . . .
N14 N 0.5322(2) 0.6325(2) 0.4779(2) 0.0405(8) Uani 1 1 d . . . . .
N20 N 0.0939(2) 0.6223(2) 0.4902(2) 0.0340(7) Uani 1 1 d . . . . .
N7 N 0.7079(2) 0.5348(2) 0.2405(2) 0.0491(9) Uani 1 1 d . . . . .
H7A H 0.771444 0.525894 0.267824 0.059 Uiso 1 1 calc R . . . .
H7B H 0.659636 0.522343 0.265726 0.059 Uiso 1 1 calc R . . . .
N2 N 0.7655(2) 0.7164(2) -0.2331(2) 0.0474(9) Uani 1 1 d . . . . .
H2A H 0.790715 0.684385 -0.268261 0.057 Uiso 1 1 d GR . . . .
H2B H 0.699128 0.716520 -0.251199 0.057 Uiso 1 1 d GR . . . .
C6 C 0.5381(2) 0.6128(2) 0.0404(2) 0.0299(7) Uani 1 1 d . . . . .
N17 N 0.2163(2) 0.7178(2) 0.7433(2) 0.0468(8) Uani 1 1 d . . . . .
H17A H 0.274901 0.745220 0.751522 0.056 Uiso 1 1 d GR . . . .
H17B H 0.170361 0.756004 0.750591 0.056 Uiso 1 1 d GR . . . .
C14 C 0.0399(2) 0.6386(2) 0.5464(2) 0.0307(7) Uani 1 1 d . . . . .
C1 C 0.7949(2) 0.6793(2) -0.1515(2) 0.0314(7) Uani 1 1 d . . . . .
C2 C 0.9335(2) 0.6363(2) -0.0380(2) 0.0298(7) Uani 1 1 d . . . . .
C13 C 0.1896(2) 0.6837(2) 0.6608(2) 0.0325(7) Uani 1 1 d . . . . .
C10 C 0.4301(2) 0.6130(2) 0.4574(2) 0.0298(7) Uani 1 1 d . . . . .
N12 N 0.2552(2) 0.5334(2) 0.2640(2) 0.0516(9) Uani 1 1 d . . . . .
H12A H 0.302877 0.498430 0.255125 0.062 Uiso 1 1 d GR . . . .
H12B H 0.199487 0.502403 0.259368 0.062 Uiso 1 1 d GR . . . .
C9 C 0.2874(2) 0.5679(2) 0.3468(2) 0.0336(8) Uani 1 1 d . . . . .
C5 C 0.6842(2) 0.5680(2) 0.1593(2) 0.0328(8) Uani 1 1 d . . . . .
C8 C 0.3812(3) 0.6514(3) -0.0682(2) 0.0447(10) Uani 1 1 d . . . . .
H8A H 0.410483 0.705587 -0.084926 0.067 Uiso 1 1 calc GR . . . .
H8B H 0.309651 0.661276 -0.070745 0.067 Uiso 1 1 calc GR . . . .
H8C H 0.387311 0.603589 -0.107595 0.067 Uiso 1 1 calc GR . . . .
C12 C 0.5888(3) 0.6523(3) 0.5668(3) 0.0461(10) Uani 1 1 d . . . . .
H12C H 0.553391 0.698399 0.590507 0.069 Uiso 1 1 calc GR . . . .
H12D H 0.656907 0.672882 0.567192 0.069 Uiso 1 1 calc GR . . . .
H12E H 0.593774 0.598831 0.601980 0.069 Uiso 1 1 calc GR . . . .
C4 C 1.0888(3) 0.5957(3) 0.0755(3) 0.0448(9) Uani 1 1 d . . . . .
H4A H 1.077071 0.641591 0.114828 0.067 Uiso 1 1 calc GR . . . .
H4B H 1.161569 0.590268 0.080716 0.067 Uiso 1 1 calc GR . . . .
H4C H 1.062362 0.539253 0.090046 0.067 Uiso 1 1 calc GR . . . .
C15 C -0.1217(3) 0.6394(3) 0.5930(3) 0.0462(10) Uani 1 1 d . . . . .
H15A H -0.081747 0.620899 0.649907 0.069 Uiso 1 1 calc GR . . . .
H15B H -0.184234 0.604693 0.576941 0.069 Uiso 1 1 calc GR . . . .
H15C H -0.138447 0.702182 0.594368 0.069 Uiso 1 1 calc GR . . . .
C3 C 1.1009(3) 0.6267(3) -0.0745(3) 0.0416(9) Uani 1 1 d . . . . .
H3A H 1.061413 0.609761 -0.132168 0.062 Uiso 1 1 calc GR . . . .
H3B H 1.159178 0.587179 -0.056253 0.062 Uiso 1 1 calc GR . . . .
H3C H 1.124571 0.687632 -0.075705 0.062 Uiso 1 1 calc GR . . . .
C7 C 0.3744(3) 0.6171(3) 0.0832(3) 0.0443(10) Uani 1 1 d . . . . .
H7C H 0.353171 0.555447 0.084470 0.066 Uiso 1 1 calc GR . . . .
H7D H 0.314492 0.655060 0.066583 0.066 Uiso 1 1 calc GR . . . .
H7E H 0.414881 0.634306 0.140439 0.066 Uiso 1 1 calc GR . . . .
C16 C -0.1205(3) 0.6022(3) 0.4415(3) 0.0488(10) Uani 1 1 d . . . . .
H16A H -0.124196 0.653733 0.403990 0.073 Uiso 1 1 calc GR . . . .
H16B H -0.189064 0.584149 0.442553 0.073 Uiso 1 1 calc GR . . . .
H16C H -0.087026 0.553486 0.419484 0.073 Uiso 1 1 calc GR . . . .
C11 C 0.5943(3) 0.6213(3) 0.4161(3) 0.0429(9) Uani 1 1 d . . . . .
H11A H 0.618716 0.560347 0.418249 0.064 Uiso 1 1 calc GR . . . .
H11B H 0.652164 0.661737 0.430830 0.064 Uiso 1 1 calc GR . . . .
H11C H 0.553316 0.634562 0.357942 0.064 Uiso 1 1 calc GR . . . .
H5 H 0.913(3) 0.602(2) 0.061(2) 0.029(10) Uiso 1 1 d . . . . .
H10 H 0.558(3) 0.646(2) -0.060(3) 0.035(11) Uiso 1 1 d . . . . .
H6 H 0.814(3) 0.570(3) 0.152(3) 0.047(11) Uiso 1 1 d . . . . .
H1 H 0.668(3) 0.668(3) -0.143(3) 0.066(15) Uiso 1 1 d . . . . .
H8 H 0.543(3) 0.562(3) 0.157(3) 0.049(12) Uiso 1 1 d . . . . .
H18 H 0.053(3) 0.686(2) 0.658(2) 0.031(10) Uiso 1 1 d . . . . .
H11 H 0.161(3) 0.571(3) 0.360(3) 0.043(11) Uiso 1 1 d . . . . .
H16 H 0.312(3) 0.670(3) 0.646(3) 0.044(12) Uiso 1 1 d . . . . .
H15 H 0.410(3) 0.644(3) 0.561(3) 0.041(12) Uiso 1 1 d . . . . .
H20 H 0.057(3) 0.599(2) 0.443(2) 0.036(11) Uiso 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
Ni1 N1 1.839(3) . ?
Ni1 N5 1.839(3) . ?
Ni1 N6 1.855(3) . ?
Ni1 N10 1.867(3) . ?
Ni2 N16 1.854(3) . ?
Ni2 N15 1.845(3) . ?
Ni2 N11 1.835(3) . ?
Ni2 N20 1.869(3) . ?
N18 C14 1.370(4) . ?
N18 C13 1.356(4) . ?
N18 H18 0.76(3) . ?
N3 C1 1.339(4) . ?
N3 C2 1.346(4) . ?
N1 C1 1.307(4) . ?
N1 H1 0.79(5) . ?
N5 C2 1.315(4) . ?
N5 H5 0.77(4) . ?
N8 C6 1.362(4) . ?
N8 C5 1.370(4) . ?
N8 H8 0.87(4) . ?
N16 C13 1.275(4) . ?
N16 H16 0.78(4) . ?
N15 C10 1.311(4) . ?
N15 H15 0.77(4) . ?
O1 H1A 0.8499 . ?
O1 H1B 0.8499 . ?
N6 C5 1.288(4) . ?
N6 H6 0.89(4) . ?
N4 C2 1.358(4) . ?
N4 C4 1.443(5) . ?
N4 C3 1.446(4) . ?
N11 C9 1.308(4) . ?
N11 H11 0.83(4) . ?
N13 C10 1.353(4) . ?
N13 C9 1.350(4) . ?
O2 H2C 0.8495 . ?
O2 H2D 0.8511 . ?
N9 C6 1.342(4) . ?
N9 C8 1.443(5) . ?
N9 C7 1.449(4) . ?
N10 C6 1.292(4) . ?
N10 H10 0.82(4) . ?
N19 C14 1.342(4) . ?
N19 C15 1.448(4) . ?
N19 C16 1.441(5) . ?
N14 C10 1.354(4) . ?
N14 C12 1.443(5) . ?
N14 C11 1.442(4) . ?
N20 C14 1.300(4) . ?
N20 H20 0.86(4) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N7 C5 1.332(4) . ?
N2 H2A 0.8610 . ?
N2 H2B 0.8616 . ?
N2 C1 1.362(4) . ?
N17 H17A 0.8644 . ?
N17 H17B 0.8653 . ?
N17 C13 1.354(4) . ?
N12 H12A 0.8614 . ?
N12 H12B 0.8634 . ?
N12 C9 1.364(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C12 H12C 0.9600 . ?
C12 H12D 0.9600 . ?
C12 H12E 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C7 H7C 0.9600 . ?
C7 H7D 0.9600 . ?
C7 H7E 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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 Ni1 N5 89.30(13) . . ?
N1 Ni1 N6 179.29(15) . . ?
N1 Ni1 N10 90.62(13) . . ?
N5 Ni1 N6 90.25(13) . . ?
N5 Ni1 N10 179.35(15) . . ?
N6 Ni1 N10 89.84(13) . . ?
N16 Ni2 N20 89.83(13) . . ?
N15 Ni2 N16 90.38(13) . . ?
N15 Ni2 N20 179.44(15) . . ?
N11 Ni2 N16 179.19(16) . . ?
N11 Ni2 N15 89.43(13) . . ?
N11 Ni2 N20 90.37(13) . . ?
C14 N18 H18 119(3) . . ?
C13 N18 C14 125.5(3) . . ?
C13 N18 H18 115(3) . . ?
C1 N3 C2 119.0(3) . . ?
Ni1 N1 H1 120(3) . . ?
C1 N1 Ni1 128.9(2) . . ?
C1 N1 H1 110(3) . . ?
Ni1 N5 H5 120(3) . . ?
C2 N5 Ni1 129.4(3) . . ?
C2 N5 H5 110(3) . . ?
C6 N8 C5 125.6(3) . . ?
C6 N8 H8 122(3) . . ?
C5 N8 H8 112(3) . . ?
Ni2 N16 H16 118(3) . . ?
C13 N16 Ni2 130.1(3) . . ?
C13 N16 H16 112(3) . . ?
Ni2 N15 H15 115(3) . . ?
C10 N15 Ni2 129.6(3) . . ?
C10 N15 H15 115(3) . . ?
H1A O1 H1B 104.5 . . ?
Ni1 N6 H6 121(2) . . ?
C5 N6 Ni1 130.1(3) . . ?
C5 N6 H6 107(2) . . ?
C2 N4 C4 121.7(3) . . ?
C2 N4 C3 122.2(3) . . ?
C4 N4 C3 116.2(3) . . ?
Ni2 N11 H11 121(3) . . ?
C9 N11 Ni2 129.1(3) . . ?
C9 N11 H11 108(3) . . ?
C9 N13 C10 119.3(3) . . ?
H2C O2 H2D 104.5 . . ?
C6 N9 C8 120.2(3) . . ?
C6 N9 C7 123.0(3) . . ?
C8 N9 C7 116.8(3) . . ?
Ni1 N10 H10 119(3) . . ?
C6 N10 Ni1 130.9(3) . . ?
C6 N10 H10 109(2) . . ?
C14 N19 C15 123.2(3) . . ?
C14 N19 C16 120.3(3) . . ?
C16 N19 C15 116.3(3) . . ?
C10 N14 C12 121.6(3) . . ?
C10 N14 C11 122.4(3) . . ?
C11 N14 C12 115.4(3) . . ?
Ni2 N20 H20 117(2) . . ?
C14 N20 Ni2 130.6(3) . . ?
C14 N20 H20 111(2) . . ?
H7A N7 H7B 120.0 . . ?
C5 N7 H7A 120.0 . . ?
C5 N7 H7B 120.0 . . ?
H2A N2 H2B 109.2 . . ?
C1 N2 H2A 108.5 . . ?
C1 N2 H2B 109.8 . . ?
N9 C6 N8 115.9(3) . . ?
N10 C6 N8 120.7(3) . . ?
N10 C6 N9 123.3(3) . . ?
H17A N17 H17B 108.6 . . ?
C13 N17 H17A 109.1 . . ?
C13 N17 H17B 110.4 . . ?
N19 C14 N18 116.3(3) . . ?
N20 C14 N18 120.4(3) . . ?
N20 C14 N19 123.3(3) . . ?
N3 C1 N2 114.9(3) . . ?
N1 C1 N3 126.8(3) . . ?
N1 C1 N2 118.3(3) . . ?
N3 C2 N4 115.5(3) . . ?
N5 C2 N3 125.5(3) . . ?
N5 C2 N4 118.9(3) . . ?
N16 C13 N18 122.9(3) . . ?
N16 C13 N17 122.9(3) . . ?
N17 C13 N18 114.1(3) . . ?
N15 C10 N13 125.0(3) . . ?
N15 C10 N14 119.4(3) . . ?
N14 C10 N13 115.6(3) . . ?
H12A N12 H12B 108.9 . . ?
C9 N12 H12A 108.4 . . ?
C9 N12 H12B 109.7 . . ?
N11 C9 N13 126.4(3) . . ?
N11 C9 N12 118.8(3) . . ?
N13 C9 N12 114.8(3) . . ?
N6 C5 N8 122.0(3) . . ?
N6 C5 N7 122.9(3) . . ?
N7 C5 N8 115.0(3) . . ?
N9 C8 H8A 109.5 . . ?
N9 C8 H8B 109.5 . . ?
N9 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N14 C12 H12C 109.5 . . ?
N14 C12 H12D 109.5 . . ?
N14 C12 H12E 109.5 . . ?
H12C C12 H12D 109.5 . . ?
H12C C12 H12E 109.5 . . ?
H12D C12 H12E 109.5 . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
N4 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N19 C15 H15A 109.5 . . ?
N19 C15 H15B 109.5 . . ?
N19 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C3 H3A 109.5 . . ?
N4 C3 H3B 109.5 . . ?
N4 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N9 C7 H7C 109.5 . . ?
N9 C7 H7D 109.5 . . ?
N9 C7 H7E 109.5 . . ?
H7C C7 H7D 109.5 . . ?
H7C C7 H7E 109.5 . . ?
H7D C7 H7E 109.5 . . ?
N19 C16 H16A 109.5 . . ?
N19 C16 H16B 109.5 . . ?
N19 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N14 C11 H11A 109.5 . . ?
N14 C11 H11B 109.5 . . ?
N14 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
# start Validation Reply Form
_vrf_PLAT112_Ni_metf1            
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       b/2         92 %Fit
RESPONSE:The Ni complex is formed by one metformine molecule and one deprotonated metformine anion around a planar square Ni to give rise a complex with formula [Ni(met)(met-)]Cl*H2O. The PLATON assumes a pseudo symmetry over the metallic center generating a chemically insistent structure.
;
# end Validation Reply Form

_olex2_submission_original_sample_id MfnNi1
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.919
####################################################################### 
# 
# 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_metzn
_database_code_depnum_ccdc_archive 'CCDC 1998786'
loop_
_audit_author_name
_audit_author_address
'Richard DVries'
;Universidad Santiago de Cali
Colombia
;
_audit_update_record             
;
2020-04-23 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_audit_creation_date             2019-10-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        MetZn
_chemical_formula_moiety         'C4 H12 Cl3 N5 Zn'
_chemical_formula_sum            'C4 H12 Cl3 N5 Zn'
_chemical_formula_weight         301.91
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C4 H12 N5 Cl3 Zn '
_chemical_oxdiff_usercomment     'Amostra Richard, aluna Laura Porras'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.5200(12)
_cell_length_b                   7.5140(6)
_cell_length_c                   13.0298(13)
_cell_angle_alpha                90
_cell_angle_beta                 113.199(12)
_cell_angle_gamma                90
_cell_volume                     1126.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1889
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.2890
_cell_measurement_theta_min      3.1600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.856
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5154
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.993
_diffrn_reflns_theta_min         3.156
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00   5.00   1.00   24.95    --   27.63  54.00 -90.00   38
  2  ω    -66.00 118.00   1.00   24.95    --   27.63  54.00-150.00  184
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0347183000
_diffrn_orient_matrix_UB_12      -0.0006757000
_diffrn_orient_matrix_UB_13      -0.0581691000
_diffrn_orient_matrix_UB_21      0.0252227000
_diffrn_orient_matrix_UB_22      0.0817104000
_diffrn_orient_matrix_UB_23      -0.0062466000
_diffrn_orient_matrix_UB_31      0.0443105000
_diffrn_orient_matrix_UB_32      -0.0471219000
_diffrn_orient_matrix_UB_33      -0.0094271000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2331
_reflns_number_total             2966
_reflns_odcompleteness_completeness 99.88
_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 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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         0.501
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2966
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.090
_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)+(0.0351P)²+0.2250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0928
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N1(H1A,H1B), N2(H2A,H2B)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4C,H4D,H4E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Zn1 Zn 0.71906(3) 0.13797(4) 0.70170(3) 0.02710(11) Uani 1 1 d . . . . .
Cl1 Cl 0.86386(6) 0.15417(11) 0.87128(6) 0.03711(19) Uani 1 1 d . . . . .
Cl2 Cl 0.53957(6) 0.09938(11) 0.69745(6) 0.03697(19) Uani 1 1 d . . . . .
Cl3 Cl 0.75845(8) -0.07346(10) 0.59836(7) 0.0451(2) Uani 1 1 d . . . . .
N3 N 0.7162(2) 0.3719(3) 0.6180(2) 0.0250(5) Uani 1 1 d . . . . .
N5 N 0.8266(2) 0.5579(3) 0.7625(2) 0.0299(5) Uani 1 1 d . . . . .
N4 N 0.8843(2) 0.5042(4) 0.6194(2) 0.0357(6) Uani 1 1 d . . . . .
H4A H 0.946446 0.565847 0.652030 0.043 Uiso 1 1 calc R . . . .
H4B H 0.871155 0.455061 0.555961 0.043 Uiso 1 1 calc R . . . .
N1 N 0.6318(2) 0.5524(3) 0.4615(2) 0.0384(6) Uani 1 1 d . . . . .
H1A H 0.584018 0.564510 0.393117 0.046 Uiso 1 1 calc R . . . .
H1B H 0.669668 0.643074 0.498299 0.046 Uiso 1 1 calc R . . . .
N2 N 0.5886(2) 0.2575(4) 0.4526(2) 0.0409(7) Uani 1 1 d . . . . .
H2A H 0.541028 0.270904 0.384305 0.049 Uiso 1 1 calc R . . . .
H2B H 0.597930 0.154222 0.483405 0.049 Uiso 1 1 calc R . . . .
C2 C 0.8091(2) 0.4852(3) 0.6667(2) 0.0240(5) Uani 1 1 d . . . . .
C1 C 0.6470(2) 0.3946(4) 0.5099(2) 0.0269(6) Uani 1 1 d . . . . .
C3 C 0.7350(3) 0.5741(5) 0.8043(3) 0.0457(8) Uani 1 1 d . . . . .
H3A H 0.717630 0.697550 0.808689 0.069 Uiso 1 1 calc GR . . . .
H3B H 0.760428 0.521490 0.877219 0.069 Uiso 1 1 calc GR . . . .
H3C H 0.666607 0.513749 0.754588 0.069 Uiso 1 1 calc GR . . . .
C4 C 0.9362(3) 0.6451(5) 0.8286(3) 0.0526(10) Uani 1 1 d . . . . .
H4C H 0.999626 0.573480 0.828360 0.079 Uiso 1 1 calc GR . . . .
H4D H 0.942432 0.659735 0.903922 0.079 Uiso 1 1 calc GR . . . .
H4E H 0.938882 0.759661 0.797008 0.079 Uiso 1 1 calc GR . . . .


_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
Zn1 Cl1 2.2422(9) . ?
Zn1 Cl2 2.2447(8) . ?
Zn1 Cl3 2.2590(9) . ?
Zn1 N3 2.062(2) . ?
N3 C2 1.377(3) . ?
N3 C1 1.342(4) . ?
N5 C2 1.300(3) . ?
N5 C3 1.455(4) . ?
N5 C4 1.457(4) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C2 1.321(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.321(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C1 1.313(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4C 0.9600 . ?
C4 H4D 0.9600 . ?
C4 H4E 0.9600 . ?

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
Cl1 Zn1 Cl2 116.38(3) . . ?
Cl1 Zn1 Cl3 110.12(3) . . ?
Cl2 Zn1 Cl3 110.24(3) . . ?
N3 Zn1 Cl1 108.29(7) . . ?
N3 Zn1 Cl2 106.77(7) . . ?
N3 Zn1 Cl3 104.28(7) . . ?
C2 N3 Zn1 116.57(18) . . ?
C1 N3 Zn1 122.22(18) . . ?
C1 N3 C2 118.9(2) . . ?
C2 N5 C3 122.3(3) . . ?
C2 N5 C4 121.3(3) . . ?
C3 N5 C4 116.0(3) . . ?
H4A N4 H4B 120.0 . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
N5 C2 N3 119.7(2) . . ?
N5 C2 N4 121.4(3) . . ?
N4 C2 N3 118.7(2) . . ?
N1 C1 N3 121.8(3) . . ?
N2 C1 N3 118.8(3) . . ?
N2 C1 N1 119.3(3) . . ?
N5 C3 H3A 109.5 . . ?
N5 C3 H3B 109.5 . . ?
N5 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N5 C4 H4C 109.5 . . ?
N5 C4 H4D 109.5 . . ?
N5 C4 H4E 109.5 . . ?
H4C C4 H4D 109.5 . . ?
H4C C4 H4E 109.5 . . ?
H4D C4 H4E 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.172
_oxdiff_exptl_absorpt_empirical_full_min 0.934
####################################################################### 
# 
# 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_Cu_metf1
_database_code_depnum_ccdc_archive 'CCDC 1998784'
loop_
_audit_author_name
_audit_author_address
'Richard DVries'
;Universidad Santiago de Cali
Colombia
;
_audit_update_record             
;
2020-04-23 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_audit_creation_date             2019-07-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        MFNCu1
_chemical_formula_moiety         'C8 H22 Cu N10, 2(Cl), 2(H2 O)'
_chemical_formula_sum            'C8 H26 Cl2 Cu N10 O2'
_chemical_formula_weight         428.83
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Cu N5 C6 H10 Cl O'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.1596(14)
_cell_length_b                   11.562(2)
_cell_length_c                   15.091(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.63(3)
_cell_angle_gamma                90
_cell_volume                     895.9(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1008
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.3770
_cell_measurement_theta_min      2.7150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.541
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             446
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0910
_diffrn_reflns_av_unetI/netI     0.0868
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5415
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.492
_diffrn_reflns_theta_min         2.712
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 113.00   1.00   60.00    --   27.63  54.00 -30.00  182
  2  ω     13.00  56.00   1.00   60.00    --   27.63  54.00-120.00   43
  3  ω    -69.00 -39.00   1.00   60.00    --   27.63  54.00-180.00   30
  4  ω     43.00 113.00   1.00   60.00    --   27.63  54.00-180.00   70
  5  ω      7.00  33.00   1.00   60.00    --   27.63  54.00  90.00   26
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0261054000
_diffrn_orient_matrix_UB_12      0.0050337000
_diffrn_orient_matrix_UB_13      0.0468768000
_diffrn_orient_matrix_UB_21      0.0366604000
_diffrn_orient_matrix_UB_22      0.0586281000
_diffrn_orient_matrix_UB_23      -0.0049331000
_diffrn_orient_matrix_UB_31      -0.1306919000
_diffrn_orient_matrix_UB_32      0.0172502000
_diffrn_orient_matrix_UB_33      0.0029841000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1138
_reflns_number_total             1863
_reflns_odcompleteness_completeness 99.85
_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 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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         0.586
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1863
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0585
_refine_ls_restrained_S_all      1.040
_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)+(0.0569P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1570
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 N2-H2A
 0.9 with sigma of 0.02
 N2-H2B
 0.9 with sigma of 0.02
3.a Free rotating group:
 O1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N1(H1), N5(H5)
3.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
;
_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
Cu1 Cu 1.000000 0.500000 0.500000 0.0401(3) Uani 1 2 d S T P . .
Cl1 Cl 0.3212(3) 0.15839(13) 0.71588(13) 0.0671(5) Uani 1 1 d . . . . .
N3 N 0.5946(8) 0.6191(3) 0.6281(3) 0.0426(12) Uani 1 1 d . . . . .
H3 H 0.488186 0.649951 0.661637 0.051 Uiso 1 1 calc R . . . .
O1 O 0.7792(9) 0.1886(4) 0.5996(3) 0.0672(14) Uani 1 1 d . . . . .
H1A H 0.661949 0.178289 0.634568 0.101 Uiso 1 1 d G . . . .
H1B H 0.921008 0.173502 0.631005 0.101 Uiso 1 1 d G . . . .
N1 N 0.7540(9) 0.4445(4) 0.5785(3) 0.0457(12) Uani 1 1 d . . . . .
H1 H 0.745360 0.370457 0.582706 0.055 Uiso 1 1 calc R . . . .
N5 N 0.9016(9) 0.6566(3) 0.5292(3) 0.0499(13) Uani 1 1 d . . . . .
H5 H 0.978587 0.709875 0.501865 0.060 Uiso 1 1 calc R . . . .
N4 N 0.6979(10) 0.8072(3) 0.5984(3) 0.0513(14) Uani 1 1 d . . . . .
C1 C 0.5995(10) 0.5007(4) 0.6261(4) 0.0388(12) Uani 1 1 d . . . . .
N2 N 0.4319(11) 0.4516(4) 0.6756(4) 0.0604(16) Uani 1 1 d D . . . .
C2 C 0.7398(10) 0.6941(4) 0.5828(4) 0.0392(13) Uani 1 1 d . . . . .
C3 C 0.5379(14) 0.8489(5) 0.6644(5) 0.074(2) Uani 1 1 d . . . . .
H3A H 0.365576 0.817610 0.652950 0.111 Uiso 1 1 calc GR . . . .
H3B H 0.529855 0.931811 0.661892 0.111 Uiso 1 1 calc GR . . . .
H3C H 0.611656 0.825153 0.722423 0.111 Uiso 1 1 calc GR . . . .
C4 C 0.8213(14) 0.8948(5) 0.5477(5) 0.077(2) Uani 1 1 d . . . . .
H4A H 1.006207 0.892935 0.563193 0.115 Uiso 1 1 calc GR . . . .
H4B H 0.755186 0.969648 0.561272 0.115 Uiso 1 1 calc GR . . . .
H4C H 0.784022 0.879553 0.485232 0.115 Uiso 1 1 calc GR . . . .
H2A H 0.358(12) 0.499(4) 0.711(4) 0.07(2) Uiso 1 1 d D . . . .
H2B H 0.411(11) 0.3746(19) 0.676(4) 0.063(18) 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
Cu1 N1 1.929(4) . ?
Cu1 N1 1.929(4) 3_766 ?
Cu1 N5 1.942(4) 3_766 ?
Cu1 N5 1.942(4) . ?
N3 H3 0.8600 . ?
N3 C1 1.370(6) . ?
N3 C2 1.371(6) . ?
O1 H1A 0.8493 . ?
O1 H1B 0.8499 . ?
N1 H1 0.8600 . ?
N1 C1 1.298(6) . ?
N5 H5 0.8600 . ?
N5 C2 1.294(6) . ?
N4 C2 1.349(6) . ?
N4 C3 1.438(6) . ?
N4 C4 1.453(7) . ?
C1 N2 1.325(7) . ?
N2 H2A 0.88(2) . ?
N2 H2B 0.90(2) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

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 Cu1 N1 180.00(18) . 3_766 ?
N1 Cu1 N5 91.81(17) 3_766 . ?
N1 Cu1 N5 91.81(17) . 3_766 ?
N1 Cu1 N5 88.19(17) . . ?
N1 Cu1 N5 88.19(17) 3_766 3_766 ?
N5 Cu1 N5 180.0 . 3_766 ?
C1 N3 H3 116.2 . . ?
C1 N3 C2 127.5(4) . . ?
C2 N3 H3 116.2 . . ?
H1A O1 H1B 104.6 . . ?
Cu1 N1 H1 114.7 . . ?
C1 N1 Cu1 130.6(3) . . ?
C1 N1 H1 114.7 . . ?
Cu1 N5 H5 114.6 . . ?
C2 N5 Cu1 130.8(4) . . ?
C2 N5 H5 114.6 . . ?
C2 N4 C3 123.9(4) . . ?
C2 N4 C4 119.9(4) . . ?
C3 N4 C4 116.2(4) . . ?
N1 C1 N3 121.7(4) . . ?
N1 C1 N2 124.6(5) . . ?
N2 C1 N3 113.7(4) . . ?
C1 N2 H2A 115(4) . . ?
C1 N2 H2B 121(4) . . ?
H2A N2 H2B 124(5) . . ?
N5 C2 N3 121.1(4) . . ?
N5 C2 N4 123.9(5) . . ?
N4 C2 N3 114.9(4) . . ?
N4 C3 H3A 109.5 . . ?
N4 C3 H3B 109.5 . . ?
N4 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
N4 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

_olex2_submission_original_sample_id MFNCu1
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.749
_oxdiff_exptl_absorpt_empirical_full_min 0.432
