# 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. 
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data_pg31
_database_code_depnum_ccdc_archive 'CCDC 916613'
_audit_update_record             
;
2012-12-20 deposited with the CCDC.
2015-07-13 downloaded from the CCDC.
;
#TrackingRef '16323_web_deposit_cif_file_0_hemantmande_1355983678.pg31.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C8 H11 Cl N), Cl4 Co, Cl'
_chemical_formula_sum            'C24 H33 Cl8 Co N3'
_chemical_formula_weight         706.06
_chemical_absolute_configuration syn
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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.7886(2)
_cell_length_b                   7.5549(1)
_cell_length_c                   15.5888(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.963(1)
_cell_angle_gamma                90.00
_cell_volume                     1617.82(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9912
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      35.06

_exptl_crystal_description       rectangular
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             722
_exptl_absorpt_coefficient_mu    1.210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6205
_exptl_absorpt_correction_T_max  0.8009
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18805
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         33.72
_reflns_number_total             10842
_reflns_number_gt                9872
_reflns_threshold_expression     >2sigma(I)

_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          
;
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)+(0.0221P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.011(7)
_refine_ls_number_reflns         10842
_refine_ls_number_parameters     457
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0587
_refine_ls_wR_factor_gt          0.0569
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.161622(13) 0.02341(3) 0.490266(11) 0.01882(4) Uani 1 1 d . . .
Cl1 Cl 0.21906(2) -0.25817(5) 0.47529(2) 0.02350(7) Uani 1 1 d . . .
Cl2 Cl 0.16070(2) 0.06476(5) 0.63592(2) 0.02316(7) Uani 1 1 d . . .
Cl3 Cl 0.25807(3) 0.24126(5) 0.44657(2) 0.02792(7) Uani 1 1 d . . .
Cl4 Cl 0.00901(2) 0.04935(5) 0.42436(2) 0.02595(7) Uani 1 1 d . . .
Cl5 Cl 0.47608(3) 0.49773(5) 0.62112(2) 0.02473(7) Uani 1 1 d . . .
C1 C 0.08047(15) 0.6796(2) 0.25947(12) 0.0325(4) Uani 1 1 d . . .
H1A H 0.011(2) 0.685(4) 0.2469(17) 0.058(7) Uiso 1 1 d . . .
H1B H 0.1038(17) 0.775(4) 0.2968(15) 0.048(7) Uiso 1 1 d . . .
H1C H 0.1116(15) 0.688(3) 0.2035(14) 0.037(6) Uiso 1 1 d . . .
C2 C 0.10956(10) 0.4981(2) 0.29525(9) 0.0223(3) Uani 1 1 d . . .
H2 H 0.1766(14) 0.490(3) 0.3087(11) 0.025(5) Uiso 1 1 d . . .
N1 N 0.06389(10) 0.47110(19) 0.37842(8) 0.0226(2) Uani 1 1 d . . .
H1D H 0.0867(14) 0.548(3) 0.4154(13) 0.030(5) Uiso 1 1 d . . .
H1E H 0.0729(16) 0.362(3) 0.4003(14) 0.038(6) Uiso 1 1 d . . .
H1F H -0.0062(16) 0.491(3) 0.3743(13) 0.039(6) Uiso 1 1 d . . .
C3 C 0.08287(11) 0.3486(2) 0.23402(9) 0.0226(3) Uani 1 1 d . . .
C4 C -0.01255(12) 0.3213(2) 0.19893(10) 0.0271(3) Uani 1 1 d . . .
H4 H -0.0624(15) 0.397(3) 0.2157(13) 0.035(5) Uiso 1 1 d . . .
C5 C -0.03363(14) 0.1878(2) 0.13945(10) 0.0310(3) Uani 1 1 d . . .
H5 H -0.0994(19) 0.164(4) 0.1163(14) 0.049(6) Uiso 1 1 d . . .
C6 C 0.04061(15) 0.0829(2) 0.11426(10) 0.0342(4) Uani 1 1 d . . .
Cl6 Cl 0.01490(5) -0.07986(8) 0.03681(3) 0.05267(14) Uani 1 1 d . . .
C7 C 0.13518(15) 0.1065(3) 0.14821(12) 0.0391(4) Uani 1 1 d . . .
H7 H 0.1869(16) 0.029(4) 0.1305(13) 0.040(5) Uiso 1 1 d . . .
C8 C 0.15558(13) 0.2385(3) 0.20880(11) 0.0331(3) Uani 1 1 d . . .
H8 H 0.2214(16) 0.248(3) 0.2359(13) 0.036(5) Uiso 1 1 d . . .
C9 C 0.27231(14) 0.6814(2) 0.75864(12) 0.0311(3) Uani 1 1 d . . .
H9A H 0.3473(17) 0.678(3) 0.7548(14) 0.042(6) Uiso 1 1 d . . .
H9B H 0.2587(18) 0.711(4) 0.8167(16) 0.049(6) Uiso 1 1 d . . .
H9C H 0.2455(16) 0.775(3) 0.7233(14) 0.038(6) Uiso 1 1 d . . .
C10 C 0.22823(11) 0.5034(2) 0.73449(9) 0.0250(3) Uani 1 1 d . . .
H10 H 0.1607(15) 0.504(3) 0.7330(12) 0.029(5) Uiso 1 1 d . . .
N2 N 0.24889(11) 0.4605(2) 0.64323(8) 0.0264(3) Uani 1 1 d . . .
H2A H 0.2227(14) 0.362(3) 0.6290(12) 0.024(5) Uiso 1 1 d . . .
H2B H 0.2228(16) 0.550(3) 0.6091(14) 0.039(5) Uiso 1 1 d . . .
H2C H 0.3154(15) 0.464(3) 0.6354(11) 0.025(5) Uiso 1 1 d . . .
C11 C 0.26541(12) 0.3562(2) 0.79432(9) 0.0245(3) Uani 1 1 d . . .
C12 C 0.36454(14) 0.3181(2) 0.80711(11) 0.0316(3) Uani 1 1 d . . .
H12 H 0.4130(14) 0.385(3) 0.7775(12) 0.030(5) Uiso 1 1 d . . .
C13 C 0.39876(18) 0.1877(3) 0.86483(12) 0.0423(5) Uani 1 1 d . . .
H13 H 0.4723(19) 0.169(4) 0.8709(15) 0.054(7) Uiso 1 1 d . . .
C14 C 0.3327(2) 0.0968(3) 0.90974(12) 0.0456(5) Uani 1 1 d . . .
Cl7 Cl 0.37668(7) -0.06085(9) 0.98505(4) 0.0819(2) Uani 1 1 d . . .
C15 C 0.2354(2) 0.1305(3) 0.89865(11) 0.0472(6) Uani 1 1 d . . .
H15 H 0.1935(18) 0.070(4) 0.9256(16) 0.055(7) Uiso 1 1 d . . .
C16 C 0.20138(15) 0.2609(3) 0.84063(10) 0.0349(4) Uani 1 1 d . . .
H16 H 0.1387(18) 0.296(3) 0.8354(14) 0.039(6) Uiso 1 1 d . . .
C17 C 0.57591(11) 0.4888(2) 0.38226(11) 0.0276(3) Uani 1 1 d . . .
H17A H 0.5995(13) 0.484(3) 0.4423(12) 0.027(5) Uiso 1 1 d . . .
H17B H 0.5954(16) 0.585(3) 0.3595(14) 0.038(6) Uiso 1 1 d . . .
H17C H 0.5989(18) 0.381(4) 0.3599(15) 0.048(6) Uiso 1 1 d . . .
C18 C 0.46586(10) 0.4877(2) 0.37772(9) 0.0219(3) Uani 1 1 d . . .
H18 H 0.4408(15) 0.385(3) 0.4035(13) 0.032(5) Uiso 1 1 d . . .
N3 N 0.43423(11) 0.6341(2) 0.43334(8) 0.0252(3) Uani 1 1 d . . .
H3A H 0.4577(17) 0.734(4) 0.4172(15) 0.043(6) Uiso 1 1 d . . .
H3B H 0.3731(19) 0.647(3) 0.4305(14) 0.041(6) Uiso 1 1 d . . .
H3C H 0.4537(16) 0.614(3) 0.4912(15) 0.045(6) Uiso 1 1 d . . .
C19 C 0.41858(10) 0.5034(2) 0.28645(9) 0.0222(3) Uani 1 1 d . . .
C20 C 0.42610(13) 0.3574(2) 0.23252(11) 0.0310(3) Uani 1 1 d . . .
H20 H 0.4599(16) 0.259(3) 0.2576(14) 0.037(5) Uiso 1 1 d . . .
C21 C 0.38520(15) 0.3616(3) 0.14777(12) 0.0382(4) Uani 1 1 d . . .
H21 H 0.3905(15) 0.258(3) 0.1097(14) 0.038(5) Uiso 1 1 d . . .
C22 C 0.33482(13) 0.5110(3) 0.11861(10) 0.0366(4) Uani 1 1 d . . .
Cl8 Cl 0.27808(5) 0.51122(10) 0.01455(3) 0.06618(18) Uani 1 1 d . . .
C23 C 0.32764(14) 0.6565(3) 0.16998(10) 0.0344(4) Uani 1 1 d . . .
H23 H 0.2946(18) 0.766(4) 0.1502(16) 0.051(7) Uiso 1 1 d . . .
C24 C 0.37012(12) 0.6543(2) 0.25473(10) 0.0273(3) Uani 1 1 d . . .
H24 H 0.3679(14) 0.749(3) 0.2867(12) 0.028(5) 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
Co1 Cl3 2.2578(4) . ?
Co1 Cl4 2.2689(4) . ?
Co1 Cl1 2.2890(4) . ?
Co1 Cl2 2.2931(4) . ?
C1 C2 1.521(2) . ?
C1 H1A 0.96(3) . ?
C1 H1B 0.96(3) . ?
C1 H1C 1.01(2) . ?
C2 N1 1.5033(19) . ?
C2 C3 1.504(2) . ?
C2 H2 0.932(18) . ?
N1 H1D 0.86(2) . ?
N1 H1E 0.89(3) . ?
N1 H1F 0.97(2) . ?
C3 C8 1.386(2) . ?
C3 C4 1.396(2) . ?
C4 C5 1.384(2) . ?
C4 H4 0.95(2) . ?
C5 C6 1.378(3) . ?
C5 H5 0.96(3) . ?
C6 C7 1.376(3) . ?
C6 Cl6 1.7385(18) . ?
C7 C8 1.385(3) . ?
C7 H7 0.98(2) . ?
C8 H8 0.97(2) . ?
C9 C10 1.510(2) . ?
C9 H9A 1.04(2) . ?
C9 H9B 0.97(2) . ?
C9 H9C 0.95(2) . ?
C10 N2 1.510(2) . ?
C10 C11 1.512(2) . ?
C10 H10 0.93(2) . ?
N2 H2A 0.85(2) . ?
N2 H2B 0.92(2) . ?
N2 H2C 0.94(2) . ?
C11 C16 1.389(2) . ?
C11 C12 1.394(3) . ?
C12 C13 1.389(2) . ?
C12 H12 0.98(2) . ?
C13 C14 1.379(3) . ?
C13 H13 1.02(3) . ?
C14 C15 1.361(4) . ?
C14 Cl7 1.744(2) . ?
C15 C16 1.391(3) . ?
C15 H15 0.87(3) . ?
C16 H16 0.90(2) . ?
C17 C18 1.513(2) . ?
C17 H17A 0.965(18) . ?
C17 H17B 0.86(2) . ?
C17 H17C 0.95(3) . ?
C18 N3 1.493(2) . ?
C18 C19 1.5175(19) . ?
C18 H18 0.95(2) . ?
N3 H3A 0.87(3) . ?
N3 H3B 0.85(3) . ?
N3 H3C 0.93(2) . ?
C19 C24 1.390(2) . ?
C19 C20 1.396(2) . ?
C20 C21 1.391(3) . ?
C20 H20 0.95(2) . ?
C21 C22 1.382(3) . ?
C21 H21 0.99(2) . ?
C22 C23 1.369(3) . ?
C22 Cl8 1.7389(15) . ?
C23 C24 1.398(2) . ?
C23 H23 0.98(3) . ?
C24 H24 0.88(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
Cl3 Co1 Cl4 110.357(15) . . ?
Cl3 Co1 Cl1 115.383(16) . . ?
Cl4 Co1 Cl1 110.463(15) . . ?
Cl3 Co1 Cl2 104.672(15) . . ?
Cl4 Co1 Cl2 110.623(14) . . ?
Cl1 Co1 Cl2 105.022(15) . . ?
C2 C1 H1A 110.1(17) . . ?
C2 C1 H1B 112.9(15) . . ?
H1A C1 H1B 111(2) . . ?
C2 C1 H1C 104.9(13) . . ?
H1A C1 H1C 108(2) . . ?
H1B C1 H1C 109.2(19) . . ?
N1 C2 C3 110.35(12) . . ?
N1 C2 C1 108.78(13) . . ?
C3 C2 C1 113.69(12) . . ?
N1 C2 H2 106.2(11) . . ?
C3 C2 H2 106.1(12) . . ?
C1 C2 H2 111.5(13) . . ?
C2 N1 H1D 109.4(13) . . ?
C2 N1 H1E 113.5(14) . . ?
H1D N1 H1E 109(2) . . ?
C2 N1 H1F 114.1(12) . . ?
H1D N1 H1F 104.2(19) . . ?
H1E N1 H1F 106(2) . . ?
C8 C3 C4 118.74(15) . . ?
C8 C3 C2 119.19(14) . . ?
C4 C3 C2 122.02(14) . . ?
C5 C4 C3 120.43(16) . . ?
C5 C4 H4 120.6(13) . . ?
C3 C4 H4 119.0(13) . . ?
C6 C5 C4 119.45(16) . . ?
C6 C5 H5 119.1(15) . . ?
C4 C5 H5 121.4(15) . . ?
C7 C6 C5 121.24(16) . . ?
C7 C6 Cl6 119.24(14) . . ?
C5 C6 Cl6 119.51(15) . . ?
C6 C7 C8 119.03(17) . . ?
C6 C7 H7 120.2(13) . . ?
C8 C7 H7 120.8(13) . . ?
C7 C8 C3 121.09(16) . . ?
C7 C8 H8 118.4(14) . . ?
C3 C8 H8 120.4(14) . . ?
C10 C9 H9A 110.2(14) . . ?
C10 C9 H9B 109.5(16) . . ?
H9A C9 H9B 109.5(19) . . ?
C10 C9 H9C 113.0(14) . . ?
H9A C9 H9C 108.8(19) . . ?
H9B C9 H9C 106(2) . . ?
N2 C10 C9 108.75(13) . . ?
N2 C10 C11 109.99(13) . . ?
C9 C10 C11 113.17(13) . . ?
N2 C10 H10 104.3(11) . . ?
C9 C10 H10 112.7(14) . . ?
C11 C10 H10 107.6(13) . . ?
C10 N2 H2A 108.9(13) . . ?
C10 N2 H2B 107.0(14) . . ?
H2A N2 H2B 111.2(19) . . ?
C10 N2 H2C 112.6(11) . . ?
H2A N2 H2C 112.7(18) . . ?
H2B N2 H2C 104.2(19) . . ?
C16 C11 C12 118.56(16) . . ?
C16 C11 C10 120.32(16) . . ?
C12 C11 C10 121.07(14) . . ?
C13 C12 C11 120.87(17) . . ?
C13 C12 H12 117.5(12) . . ?
C11 C12 H12 121.6(12) . . ?
C14 C13 C12 118.7(2) . . ?
C14 C13 H13 125.5(15) . . ?
C12 C13 H13 115.8(15) . . ?
C15 C14 C13 121.95(18) . . ?
C15 C14 Cl7 119.67(16) . . ?
C13 C14 Cl7 118.35(19) . . ?
C14 C15 C16 119.24(18) . . ?
C14 C15 H15 121.9(17) . . ?
C16 C15 H15 118.8(18) . . ?
C11 C16 C15 120.7(2) . . ?
C11 C16 H16 116.5(15) . . ?
C15 C16 H16 122.4(15) . . ?
C18 C17 H17A 107.3(11) . . ?
C18 C17 H17B 109.4(15) . . ?
H17A C17 H17B 110.0(19) . . ?
C18 C17 H17C 110.1(15) . . ?
H17A C17 H17C 103.1(19) . . ?
H17B C17 H17C 116(2) . . ?
N3 C18 C17 108.11(12) . . ?
N3 C18 C19 111.29(12) . . ?
C17 C18 C19 113.03(12) . . ?
N3 C18 H18 103.0(13) . . ?
C17 C18 H18 112.5(13) . . ?
C19 C18 H18 108.5(12) . . ?
C18 N3 H3A 110.0(16) . . ?
C18 N3 H3B 113.4(16) . . ?
H3A N3 H3B 106(2) . . ?
C18 N3 H3C 111.6(16) . . ?
H3A N3 H3C 110(2) . . ?
H3B N3 H3C 106(2) . . ?
C24 C19 C20 119.47(13) . . ?
C24 C19 C18 123.49(13) . . ?
C20 C19 C18 117.04(14) . . ?
C21 C20 C19 120.58(17) . . ?
C21 C20 H20 123.7(14) . . ?
C19 C20 H20 115.7(14) . . ?
C22 C21 C20 118.81(17) . . ?
C22 C21 H21 120.7(13) . . ?
C20 C21 H21 120.5(13) . . ?
C23 C22 C21 121.57(15) . . ?
C23 C22 Cl8 119.71(15) . . ?
C21 C22 Cl8 118.72(15) . . ?
C22 C23 C24 119.82(17) . . ?
C22 C23 H23 123.3(15) . . ?
C24 C23 H23 116.9(15) . . ?
C19 C24 C23 119.69(16) . . ?
C19 C24 H24 120.6(13) . . ?
C23 C24 H24 119.6(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1D Cl1 0.86(2) 2.46(2) 3.2377(14) 150.9(17) 1_565
N1 H1D Cl4 0.86(2) 2.924(19) 3.3685(13) 114.3(15) 2_556
N1 H1E Cl4 0.89(3) 2.56(3) 3.3663(15) 150.0(18) .
N1 H1E Cl3 0.89(3) 2.75(2) 3.2894(14) 120.1(17) .
N1 H1F Cl2 0.97(2) 2.20(2) 3.1657(14) 174(2) 2_556
N2 H2A Cl2 0.85(2) 2.41(2) 3.2256(16) 162.1(17) .
N2 H2B Cl1 0.92(2) 2.54(2) 3.3697(14) 151.6(18) 1_565
N2 H2C Cl5 0.94(2) 2.26(2) 3.1935(16) 174.6(17) .
N3 H3A Cl5 0.87(3) 2.29(3) 3.1592(16) 178(2) 2_656
N3 H3B Cl1 0.85(3) 2.40(3) 3.1982(15) 157(2) 1_565
N3 H3C Cl5 0.93(2) 2.20(2) 3.1096(14) 164(2) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        33.72
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_pg33
_database_code_depnum_ccdc_archive 'CCDC 916614'
_audit_update_record             
;
2012-12-20 deposited with the CCDC.
2015-07-13 downloaded from the CCDC.
;
#TrackingRef '16324_web_deposit_cif_file_1_hemantmande_1355983678.pg33.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C8 H11 Cl N), Cl4 Co, Cl '
_chemical_formula_sum            'C24 H33 Cl8 Co N3'
_chemical_formula_weight         706.06
_chemical_absolute_configuration syn
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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.9263(14)
_cell_length_b                   7.5981(6)
_cell_length_c                   15.8322(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.173(6)
_cell_angle_gamma                90.00
_cell_volume                     1668.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6484
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      29.13

_exptl_crystal_description       rectangular_plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             722
_exptl_absorpt_coefficient_mu    1.173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6263
_exptl_absorpt_correction_T_max  0.9120
_exptl_absorpt_process_details   'SADABS (Bruker AXS Inc., 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15274
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         28.70
_reflns_number_total             8142
_reflns_number_gt                6195
_reflns_threshold_expression     >2sigma(I)

_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          
;
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)+(0.0279P)²+0.1579P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.004(14)
_refine_ls_number_reflns         8142
_refine_ls_number_parameters     325
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0801
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.33991(2) 0.49473(5) 0.01022(2) 0.04034(10) Uani 1 1 d . . .
Cl1 Cl 0.49109(5) 0.46802(12) 0.07472(5) 0.0569(2) Uani 1 1 d . . .
Cl2 Cl 0.28160(5) 0.77325(10) 0.02536(5) 0.05063(19) Uani 1 1 d . . .
Cl3 Cl 0.24427(5) 0.27958(13) 0.05431(6) 0.0613(2) Uani 1 1 d . . .
Cl4 Cl 0.34107(5) 0.45212(11) -0.13301(5) 0.0518(2) Uani 1 1 d . . .
Cl5 Cl -0.02765(6) 0.52226(11) 0.11785(5) 0.0528(2) Uani 1 1 d . . .
N1 N 0.06740(18) -0.1186(4) 0.06662(16) 0.0530(7) Uani 1 1 d . . .
H1A H 0.1315 -0.1200 0.0688 0.079 Uiso 1 1 calc R . .
H1B H 0.0431 -0.1028 0.0132 0.079 Uiso 1 1 calc R . .
H1C H 0.0465 -0.2205 0.0858 0.079 Uiso 1 1 calc R . .
C1 C -0.0730(2) 0.0283(5) 0.1139(2) 0.0595(9) Uani 1 1 d . . .
H1D H -0.0978 0.0388 0.0555 0.089 Uiso 1 1 calc R . .
H1E H -0.0948 0.1262 0.1454 0.089 Uiso 1 1 calc R . .
H1F H -0.0957 -0.0793 0.1368 0.089 Uiso 1 1 calc R . .
C2 C 0.03593(19) 0.0273(4) 0.11996(19) 0.0468(7) Uani 1 1 d . . .
H2 H 0.0574 0.1383 0.0964 0.056 Uiso 1 1 calc R . .
C3 C 0.08076(19) 0.0127(5) 0.21041(19) 0.0499(7) Uani 1 1 d . . .
C4 C 0.1232(3) -0.1378(5) 0.2442(2) 0.0636(10) Uani 1 1 d . . .
H4 H 0.1251 -0.2387 0.2112 0.076 Uiso 1 1 calc R . .
C5 C 0.1637(3) -0.1393(7) 0.3286(3) 0.0862(14) Uani 1 1 d . . .
H5 H 0.1941 -0.2399 0.3514 0.103 Uiso 1 1 calc R . .
C6 C 0.1581(3) 0.0098(8) 0.3772(2) 0.0857(13) Uani 1 1 d . . .
Cl6 Cl 0.20978(18) 0.0064(3) 0.48055(9) 0.1725(9) Uani 1 1 d . . .
C7 C 0.1131(4) 0.1584(7) 0.3447(3) 0.0907(15) Uani 1 1 d . . .
H7 H 0.1072 0.2566 0.3790 0.109 Uiso 1 1 calc R . .
C8 C 0.0768(3) 0.1616(6) 0.2613(3) 0.0690(11) Uani 1 1 d . . .
H8 H 0.0492 0.2644 0.2384 0.083 Uiso 1 1 calc R . .
N2 N 0.2540(2) 0.0547(4) 0.85944(16) 0.0563(7) Uani 1 1 d . . .
H2A H 0.2742 -0.0318 0.8946 0.084 Uiso 1 1 calc R . .
H2B H 0.1911 0.0713 0.8620 0.084 Uiso 1 1 calc R . .
H2C H 0.2856 0.1533 0.8745 0.084 Uiso 1 1 calc R . .
C9 C 0.2265(3) -0.1676(5) 0.7482(3) 0.0690(10) Uani 1 1 d . . .
H9A H 0.2385 -0.1995 0.6914 0.103 Uiso 1 1 calc R . .
H9B H 0.1582 -0.1589 0.7520 0.103 Uiso 1 1 calc R . .
H9C H 0.2529 -0.2559 0.7870 0.103 Uiso 1 1 calc R . .
C10 C 0.2729(2) 0.0063(5) 0.77035(19) 0.0533(7) Uani 1 1 d . . .
H10 H 0.3427 -0.0073 0.7687 0.064 Uiso 1 1 calc R . .
C11 C 0.2399(3) 0.1529(5) 0.7102(2) 0.0527(8) Uani 1 1 d . . .
C12 C 0.1445(3) 0.2038(6) 0.6986(3) 0.0734(12) Uani 1 1 d . . .
H12 H 0.0995 0.1490 0.7298 0.088 Uiso 1 1 calc R . .
C13 C 0.1149(4) 0.3332(7) 0.6422(3) 0.1031(18) Uani 1 1 d . . .
H13 H 0.0505 0.3671 0.6348 0.124 Uiso 1 1 calc R . .
C14 C 0.1823(7) 0.4120(7) 0.5966(3) 0.111(2) Uani 1 1 d . . .
Cl7 Cl 0.1443(2) 0.5733(3) 0.52289(13) 0.2059(12) Uani 1 1 d . . .
C15 C 0.2746(6) 0.3663(8) 0.6051(3) 0.106(2) Uani 1 1 d . . .
H15 H 0.3183 0.4209 0.5725 0.127 Uiso 1 1 calc R . .
C16 C 0.3054(3) 0.2367(6) 0.6630(2) 0.0766(13) Uani 1 1 d . . .
H16 H 0.3703 0.2059 0.6701 0.092 Uiso 1 1 calc R . .
N3 N 0.43523(17) 0.0450(4) 0.12315(15) 0.0485(6) Uani 1 1 d . . .
H3A H 0.4192 0.1513 0.1029 0.073 Uiso 1 1 calc R . .
H3B H 0.4135 -0.0366 0.0858 0.073 Uiso 1 1 calc R . .
H3C H 0.4991 0.0371 0.1321 0.073 Uiso 1 1 calc R . .
C19 C 0.4178(3) -0.1639(6) 0.2390(3) 0.0750(12) Uani 1 1 d . . .
H19A H 0.3979 -0.2508 0.1970 0.113 Uiso 1 1 calc R . .
H19B H 0.3862 -0.1855 0.2895 0.113 Uiso 1 1 calc R . .
H19C H 0.4864 -0.1705 0.2521 0.113 Uiso 1 1 calc R . .
C20 C 0.3911(2) 0.0167(5) 0.20530(19) 0.0509(7) Uani 1 1 d . . .
H20 H 0.3208 0.0200 0.1931 0.061 Uiso 1 1 calc R . .
C21 C 0.4191(2) 0.1633(5) 0.2660(2) 0.0497(8) Uani 1 1 d . . .
C22 C 0.5119(2) 0.1846(5) 0.3023(2) 0.0587(9) Uani 1 1 d . . .
H22 H 0.5602 0.1106 0.2862 0.070 Uiso 1 1 calc R . .
C23 C 0.5347(3) 0.3125(6) 0.3616(2) 0.0690(10) Uani 1 1 d . . .
H23 H 0.5979 0.3264 0.3852 0.083 Uiso 1 1 calc R . .
C24 C 0.4627(4) 0.4203(6) 0.3858(2) 0.0717(11) Uani 1 1 d . . .
Cl8 Cl 0.48988(13) 0.5796(2) 0.46308(9) 0.1200(5) Uani 1 1 d . . .
C25 C 0.3711(4) 0.4036(7) 0.3506(3) 0.0891(14) Uani 1 1 d . . .
H25 H 0.3229 0.4775 0.3672 0.107 Uiso 1 1 calc R . .
C26 C 0.3496(3) 0.2759(6) 0.2901(3) 0.0727(11) Uani 1 1 d . . .
H26 H 0.2868 0.2658 0.2651 0.087 Uiso 1 1 calc R . .


_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 Cl3 2.2586(9) . ?
Co1 Cl1 2.2647(8) . ?
Co1 Cl2 2.2870(8) . ?
Co1 Cl4 2.2921(9) . ?
N1 C2 1.484(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C1 C2 1.512(4) . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 H1F 0.9600 . ?
C2 C3 1.514(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.373(5) . ?
C3 C8 1.393(5) . ?
C4 C5 1.402(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.370(7) . ?
C6 Cl6 1.727(4) . ?
C7 C8 1.371(6) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
N2 C10 1.504(4) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C9 C10 1.499(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.510(5) . ?
C10 H10 0.9800 . ?
C11 C12 1.380(5) . ?
C11 C16 1.386(5) . ?
C12 C13 1.367(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.325(8) . ?
C14 Cl7 1.741(5) . ?
C15 C16 1.387(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
N3 C20 1.503(4) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
C19 C20 1.507(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.499(5) . ?
C20 H20 0.9800 . ?
C21 C26 1.371(5) . ?
C21 C22 1.376(5) . ?
C22 C23 1.369(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.375(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.352(6) . ?
C24 Cl8 1.739(4) . ?
C25 C26 1.378(7) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

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
Cl3 Co1 Cl1 110.24(3) . . ?
Cl3 Co1 Cl2 114.36(4) . . ?
Cl1 Co1 Cl2 111.11(3) . . ?
Cl3 Co1 Cl4 105.10(4) . . ?
Cl1 Co1 Cl4 110.14(3) . . ?
Cl2 Co1 Cl4 105.58(3) . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
N1 C2 C1 108.3(2) . . ?
N1 C2 C3 111.5(3) . . ?
C1 C2 C3 112.7(3) . . ?
N1 C2 H2 108.1 . . ?
C1 C2 H2 108.1 . . ?
C3 C2 H2 108.1 . . ?
C4 C3 C8 119.3(3) . . ?
C4 C3 C2 123.8(3) . . ?
C8 C3 C2 116.9(3) . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.2(4) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C7 C6 C5 121.1(4) . . ?
C7 C6 Cl6 120.4(4) . . ?
C5 C6 Cl6 118.6(4) . . ?
C6 C7 C8 119.5(4) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C3 120.8(4) . . ?
C7 C8 H8 119.6 . . ?
C3 C8 H8 119.6 . . ?
C10 N2 H2A 109.5 . . ?
C10 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C10 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C9 C10 N2 109.1(3) . . ?
C9 C10 C11 113.7(3) . . ?
N2 C10 C11 110.0(3) . . ?
C9 C10 H10 108.0 . . ?
N2 C10 H10 108.0 . . ?
C11 C10 H10 108.0 . . ?
C12 C11 C16 118.2(4) . . ?
C12 C11 C10 121.7(3) . . ?
C16 C11 C10 120.1(4) . . ?
C13 C12 C11 121.2(4) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 118.5(5) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C15 C14 C13 122.3(5) . . ?
C15 C14 Cl7 119.0(5) . . ?
C13 C14 Cl7 118.6(6) . . ?
C14 C15 C16 119.5(4) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C11 C16 C15 120.2(5) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C20 N3 H3A 109.5 . . ?
C20 N3 H3B 109.5 . . ?
H3A N3 H3B 109.5 . . ?
C20 N3 H3C 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 N3 110.2(3) . . ?
C21 C20 C19 114.1(3) . . ?
N3 C20 C19 109.2(3) . . ?
C21 C20 H20 107.7 . . ?
N3 C20 H20 107.7 . . ?
C19 C20 H20 107.7 . . ?
C26 C21 C22 118.0(4) . . ?
C26 C21 C20 119.5(3) . . ?
C22 C21 C20 122.4(3) . . ?
C23 C22 C21 121.5(3) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C22 C23 C24 118.9(4) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C25 C24 C23 121.0(4) . . ?
C25 C24 Cl8 119.5(4) . . ?
C23 C24 Cl8 119.5(4) . . ?
C24 C25 C26 119.3(4) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C21 C26 C25 121.3(4) . . ?
C21 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Cl2 0.89 2.40 3.217(3) 152.8 1_545
N1 H1B Cl5 0.89 2.27 3.113(3) 156.8 2_545
N1 H1C Cl5 0.89 2.29 3.170(3) 170.5 1_545
N2 H2A Cl2 0.89 2.54 3.382(3) 158.0 1_546
N2 H2B Cl5 0.89 2.36 3.214(3) 162.0 2_546
N2 H2C Cl4 0.89 2.40 3.252(3) 159.1 1_556
N3 H3A Cl1 0.89 2.66 3.411(3) 142.7 .
N3 H3A Cl3 0.89 2.67 3.304(3) 128.8 .
N3 H3B Cl2 0.89 2.46 3.262(3) 149.7 1_545
N3 H3B Cl1 0.89 2.97 3.434(3) 114.1 2_645
N3 H3C Cl4 0.89 2.32 3.184(3) 165.0 2_645

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.70
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_pg36
_database_code_depnum_ccdc_archive 'CCDC 916615'
_audit_update_record             
;
2012-12-20 deposited with the CCDC.
2015-07-13 downloaded from the CCDC.
;
#TrackingRef '16325_web_deposit_cif_file_2_hemantmande_1355983678.pg36.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C8 H12 N), Cl4 Co, Cl'
_chemical_formula_sum            'C24 H36 Cl5 Co N3'
_chemical_formula_weight         602.74
_chemical_absolute_configuration syn
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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.9448(2)
_cell_length_b                   7.5033(1)
_cell_length_c                   14.4057(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.471(1)
_cell_angle_gamma                90.00
_cell_volume                     1490.85(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8770
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      34.68

_exptl_crystal_description       rectangular
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             626
_exptl_absorpt_coefficient_mu    1.041
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6306
_exptl_absorpt_correction_T_max  0.8462
_exptl_absorpt_process_details   'SADABS (Bruker AXS Inc., 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15614
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.43
_diffrn_reflns_theta_max         33.73
_reflns_number_total             9553
_reflns_number_gt                8032
_reflns_threshold_expression     >2sigma(I)

_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          
;
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)+(0.0324P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.012(10)
_refine_ls_number_reflns         9553
_refine_ls_number_parameters     298
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0769
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.656135(16) 0.58240(3) -0.011900(17) 0.02195(6) Uani 1 1 d . . .
Cl1 Cl 0.66636(3) 0.63345(7) 0.14594(3) 0.02864(11) Uani 1 1 d . . .
Cl2 Cl 0.75212(4) 0.78716(10) -0.06610(4) 0.04099(15) Uani 1 1 d . . .
Cl3 Cl 0.71005(3) 0.29696(7) -0.02688(4) 0.02677(10) Uani 1 1 d . . .
Cl4 Cl 0.50117(3) 0.60899(8) -0.08457(4) 0.02988(11) Uani 1 1 d . . .
Cl5 Cl -0.02485(3) 0.10220(7) 0.13254(3) 0.02712(10) Uani 1 1 d . . .
N1 N 0.07363(12) 0.7582(3) 0.06774(12) 0.0272(4) Uani 1 1 d . . .
H1A H 0.1388 0.7682 0.0686 0.041 Uiso 1 1 calc R . .
H1B H 0.0505 0.8599 0.0908 0.041 Uiso 1 1 calc R . .
H1C H 0.0443 0.7408 0.0077 0.041 Uiso 1 1 calc R . .
C1 C -0.05666(13) 0.5910(4) 0.12412(14) 0.0283(4) Uani 1 1 d . . .
H1D H -0.0880 0.5812 0.0588 0.042 Uiso 1 1 calc R . .
H1E H -0.0803 0.6979 0.1526 0.042 Uiso 1 1 calc R . .
H1F H -0.0721 0.4854 0.1592 0.042 Uiso 1 1 calc R . .
C2 C 0.05285(13) 0.6040(3) 0.12688(13) 0.0248(4) Uani 1 1 d . . .
H2D H 0.0754 0.4931 0.0982 0.030 Uiso 1 1 calc R . .
C3 C 0.10617(13) 0.6193(3) 0.22535(13) 0.0266(4) Uani 1 1 d . . .
C4 C 0.11577(18) 0.4651(4) 0.27925(18) 0.0408(6) Uani 1 1 d . . .
H4A H 0.0926 0.3550 0.2522 0.049 Uiso 1 1 calc R . .
C5 C 0.1589(2) 0.4707(5) 0.3723(2) 0.0523(8) Uani 1 1 d . . .
H5A H 0.1643 0.3646 0.4087 0.063 Uiso 1 1 calc R . .
C6 C 0.19343(17) 0.6263(5) 0.41175(18) 0.0513(8) Uani 1 1 d . . .
H6A H 0.2229 0.6291 0.4755 0.062 Uiso 1 1 calc R . .
C7 C 0.18573(17) 0.7798(5) 0.35936(18) 0.0480(7) Uani 1 1 d . . .
H7A H 0.2107 0.8883 0.3870 0.058 Uiso 1 1 calc R . .
C8 C 0.14151(15) 0.7781(4) 0.26560(16) 0.0342(5) Uani 1 1 d . . .
H8A H 0.1358 0.8851 0.2299 0.041 Uiso 1 1 calc R . .
N2 N 0.24596(13) 0.5320(3) 0.84367(12) 0.0293(4) Uani 1 1 d . . .
H2A H 0.2753 0.4255 0.8590 0.044 Uiso 1 1 calc R . .
H2B H 0.1822 0.5247 0.8502 0.044 Uiso 1 1 calc R . .
H2C H 0.2750 0.6185 0.8823 0.044 Uiso 1 1 calc R . .
C9 C 0.20621(18) 0.7553(3) 0.71898(19) 0.0371(5) Uani 1 1 d . . .
H9A H 0.2116 0.7862 0.6538 0.056 Uiso 1 1 calc R . .
H9B H 0.2379 0.8474 0.7610 0.056 Uiso 1 1 calc R . .
H9C H 0.1376 0.7475 0.7265 0.056 Uiso 1 1 calc R . .
C10 C 0.25494(14) 0.5774(4) 0.74313(14) 0.0285(4) Uani 1 1 d . . .
H10A H 0.3254 0.5903 0.7382 0.034 Uiso 1 1 calc R . .
C11 C 0.21480(15) 0.4272(3) 0.67959(14) 0.0255(4) Uani 1 1 d . . .
C12 C 0.27459(16) 0.3306(3) 0.62935(15) 0.0315(5) Uani 1 1 d . . .
H12A H 0.3413 0.3609 0.6343 0.038 Uiso 1 1 calc R . .
C13 C 0.23831(19) 0.1902(4) 0.57197(17) 0.0403(6) Uani 1 1 d . . .
H13A H 0.2803 0.1254 0.5380 0.048 Uiso 1 1 calc R . .
C14 C 0.1425(2) 0.1447(4) 0.56408(16) 0.0403(6) Uani 1 1 d . . .
H14A H 0.1180 0.0483 0.5248 0.048 Uiso 1 1 calc R . .
C15 C 0.08137(18) 0.2391(4) 0.61322(17) 0.0389(6) Uani 1 1 d . . .
H15A H 0.0149 0.2072 0.6081 0.047 Uiso 1 1 calc R . .
C16 C 0.11715(16) 0.3808(3) 0.67027(16) 0.0324(5) Uani 1 1 d . . .
H16A H 0.0746 0.4465 0.7032 0.039 Uiso 1 1 calc R . .
N3 N 0.44541(12) 0.5226(3) 0.14102(12) 0.0275(4) Uani 1 1 d . . .
H3A H 0.4346 0.4091 0.1198 0.041 Uiso 1 1 calc R . .
H3B H 0.5103 0.5448 0.1506 0.041 Uiso 1 1 calc R . .
H3C H 0.4154 0.6004 0.0977 0.041 Uiso 1 1 calc R . .
C17 C 0.42422(18) 0.7343(4) 0.26618(17) 0.0367(5) Uani 1 1 d . . .
H17A H 0.3952 0.8177 0.2177 0.055 Uiso 1 1 calc R . .
H17B H 0.4942 0.7554 0.2797 0.055 Uiso 1 1 calc R . .
H17C H 0.3952 0.7522 0.3234 0.055 Uiso 1 1 calc R . .
C18 C 0.40573(14) 0.5450(3) 0.23172(15) 0.0274(5) Uani 1 1 d . . .
H18A H 0.3340 0.5265 0.2188 0.033 Uiso 1 1 calc R . .
C19 C 0.44769(14) 0.4062(3) 0.30132(15) 0.0256(4) Uani 1 1 d . . .
C20 C 0.38974(16) 0.2695(4) 0.32716(18) 0.0381(5) Uani 1 1 d . . .
H20A H 0.3241 0.2612 0.2983 0.046 Uiso 1 1 calc R . .
C21 C 0.4263(2) 0.1455(4) 0.3943(2) 0.0467(7) Uani 1 1 d . . .
H21A H 0.3855 0.0532 0.4110 0.056 Uiso 1 1 calc R . .
C22 C 0.5215(2) 0.1545(4) 0.43703(18) 0.0425(6) Uani 1 1 d . . .
H22A H 0.5463 0.0707 0.4839 0.051 Uiso 1 1 calc R . .
C23 C 0.58005(17) 0.2878(4) 0.41034(17) 0.0396(5) Uani 1 1 d . . .
H23A H 0.6460 0.2942 0.4386 0.048 Uiso 1 1 calc R . .
C24 C 0.54437(16) 0.4117(4) 0.34344(17) 0.0327(5) Uani 1 1 d . . .
H24A H 0.5860 0.5018 0.3258 0.039 Uiso 1 1 calc R . .


_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 Cl2 2.2515(6) . ?
Co1 Cl4 2.2670(5) . ?
Co1 Cl1 2.2895(5) . ?
Co1 Cl3 2.2906(6) . ?
N1 C2 1.490(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C1 C2 1.525(2) . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 H1F 0.9800 . ?
C2 C3 1.506(3) . ?
C2 H2D 1.0000 . ?
C3 C8 1.384(3) . ?
C3 C4 1.389(4) . ?
C4 C5 1.386(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.356(5) . ?
C5 H5A 0.9500 . ?
C6 C7 1.372(5) . ?
C6 H6A 0.9500 . ?
C7 C8 1.400(3) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
N2 C10 1.511(3) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
C9 C10 1.515(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.507(3) . ?
C10 H10A 1.0000 . ?
C11 C12 1.386(3) . ?
C11 C16 1.393(3) . ?
C12 C13 1.388(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.367(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.381(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.391(3) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
N3 C18 1.501(3) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
C17 C18 1.514(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.503(3) . ?
C18 H18A 1.0000 . ?
C19 C20 1.390(3) . ?
C19 C24 1.395(3) . ?
C20 C21 1.384(4) . ?
C20 H20A 0.9500 . ?
C21 C22 1.380(4) . ?
C21 H21A 0.9500 . ?
C22 C23 1.381(4) . ?
C22 H22A 0.9500 . ?
C23 C24 1.378(3) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9500 . ?

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
Cl2 Co1 Cl4 110.78(2) . . ?
Cl2 Co1 Cl1 106.08(2) . . ?
Cl4 Co1 Cl1 111.07(2) . . ?
Cl2 Co1 Cl3 112.66(2) . . ?
Cl4 Co1 Cl3 110.03(2) . . ?
Cl1 Co1 Cl3 106.06(2) . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
N1 C2 C3 111.65(18) . . ?
N1 C2 C1 108.26(17) . . ?
C3 C2 C1 112.52(15) . . ?
N1 C2 H2D 108.1 . . ?
C3 C2 H2D 108.1 . . ?
C1 C2 H2D 108.1 . . ?
C8 C3 C4 119.0(2) . . ?
C8 C3 C2 123.8(2) . . ?
C4 C3 C2 117.2(2) . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6A 120.1 . . ?
C7 C6 H6A 120.1 . . ?
C6 C7 C8 120.7(3) . . ?
C6 C7 H7A 119.6 . . ?
C8 C7 H7A 119.6 . . ?
C3 C8 C7 119.4(3) . . ?
C3 C8 H8A 120.3 . . ?
C7 C8 H8A 120.3 . . ?
C10 N2 H2A 109.5 . . ?
C10 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C10 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N2 109.75(18) . . ?
C11 C10 C9 113.94(18) . . ?
N2 C10 C9 108.72(18) . . ?
C11 C10 H10A 108.1 . . ?
N2 C10 H10A 108.1 . . ?
C9 C10 H10A 108.1 . . ?
C12 C11 C16 118.3(2) . . ?
C12 C11 C10 120.65(19) . . ?
C16 C11 C10 121.06(19) . . ?
C11 C12 C13 120.9(2) . . ?
C11 C12 H12A 119.6 . . ?
C13 C12 H12A 119.6 . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C13 C14 C15 119.9(2) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C14 C15 C16 120.0(2) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C15 C16 C11 120.6(2) . . ?
C15 C16 H16A 119.7 . . ?
C11 C16 H16A 119.7 . . ?
C18 N3 H3A 109.5 . . ?
C18 N3 H3B 109.5 . . ?
H3A N3 H3B 109.5 . . ?
C18 N3 H3C 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 C19 110.25(16) . . ?
N3 C18 C17 108.86(19) . . ?
C19 C18 C17 113.59(18) . . ?
N3 C18 H18A 108.0 . . ?
C19 C18 H18A 108.0 . . ?
C17 C18 H18A 108.0 . . ?
C20 C19 C24 117.9(2) . . ?
C20 C19 C18 120.34(19) . . ?
C24 C19 C18 121.7(2) . . ?
C21 C20 C19 120.9(2) . . ?
C21 C20 H20A 119.5 . . ?
C19 C20 H20A 119.5 . . ?
C22 C21 C20 120.7(2) . . ?
C22 C21 H21A 119.7 . . ?
C20 C21 H21A 119.7 . . ?
C21 C22 C23 118.7(2) . . ?
C21 C22 H22A 120.6 . . ?
C23 C22 H22A 120.6 . . ?
C24 C23 C22 121.1(2) . . ?
C24 C23 H23A 119.5 . . ?
C22 C23 H23A 119.5 . . ?
C23 C24 C19 120.7(2) . . ?
C23 C24 H24A 119.7 . . ?
C19 C24 H24A 119.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Cl3 0.91 2.29 3.1707(16) 164.1 2_655
N1 H1B Cl5 0.91 2.23 3.130(2) 171.9 1_565
N1 H1C Cl5 0.91 2.25 3.0951(18) 153.7 2
N2 H2C Cl3 0.91 2.46 3.2889(19) 151.7 2_656
N2 H2B Cl5 0.91 2.32 3.1959(18) 162.0 2_556
N2 H2A Cl1 0.91 2.34 3.226(2) 163.7 2_646
N3 H3C Cl3 0.91 2.40 3.2541(19) 156.8 2_655
N3 H3B Cl1 0.91 2.29 3.1820(18) 168.0 .
N3 H3A Cl2 0.91 2.76 3.3163(19) 120.4 2_645
N3 H3A Cl4 0.91 2.50 3.321(2) 149.8 2_645

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        33.73
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.072
####################################################################### 
# 
# 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_pg37
_database_code_depnum_ccdc_archive 'CCDC 916616'
_audit_update_record             
;
2012-12-20 deposited with the CCDC.
2015-07-13 downloaded from the CCDC.
;
#TrackingRef '16326_web_deposit_cif_file_3_hemantmande_1355983678.pg37.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H11 F N), Cl4 Co'
_chemical_formula_sum            'C16 H22 Cl4 Co F2 N2'
_chemical_formula_weight         481.09

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'
F F 0.0171 0.0103 '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                   7.1784(1)
_cell_length_b                   10.5916(1)
_cell_length_c                   14.2341(1)
_cell_angle_alpha                90.529(1)
_cell_angle_beta                 92.765(1)
_cell_angle_gamma                98.009(1)
_cell_volume                     1070.29(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9908
_cell_measurement_theta_min      3.68
_cell_measurement_theta_max      34.88

_exptl_crystal_description       rectangular
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             490
_exptl_absorpt_coefficient_mu    1.320
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7089
_exptl_absorpt_correction_T_max  0.9018
_exptl_absorpt_process_details   'SADABS (Bruker AXS Inc., 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26224
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         33.73
_reflns_number_total             8471
_reflns_number_gt                6311
_reflns_threshold_expression     >2sigma(I)

_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          
;
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)+(0.0472P)²+0.5737P] 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         8471
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.26518(3) 0.23264(2) -0.021041(17) 0.02677(7) Uani 1 1 d . . .
Cl1 Cl 0.49831(6) 0.34931(4) -0.09784(3) 0.03174(9) Uani 1 1 d . . .
Cl2 Cl 0.33700(7) 0.24251(4) 0.13707(3) 0.03223(10) Uani 1 1 d . . .
Cl3 Cl -0.00493(6) 0.31621(5) -0.05348(3) 0.03240(10) Uani 1 1 d . . .
Cl4 Cl 0.24615(8) 0.02853(5) -0.07152(3) 0.04004(12) Uani 1 1 d . . .
N1 N 0.3156(3) -0.07056(18) 0.14011(11) 0.0337(3) Uani 1 1 d . . .
H1A H 0.318(4) 0.013(3) 0.1321(19) 0.048(7) Uiso 1 1 d . . .
H1B H 0.239(5) -0.109(3) 0.100(2) 0.063(9) Uiso 1 1 d . . .
H1C H 0.436(5) -0.081(3) 0.124(2) 0.069(10) Uiso 1 1 d . . .
C1 C 0.0915(4) -0.1047(4) 0.26217(19) 0.0703(9) Uani 1 1 d . . .
H1D H 0.0041 -0.1532 0.2156 0.105 Uiso 1 1 calc R . .
H1E H 0.0707 -0.0152 0.2621 0.105 Uiso 1 1 calc R . .
H1F H 0.0697 -0.1400 0.3247 0.105 Uiso 1 1 calc R . .
C2 C 0.2847(4) -0.1132(3) 0.23843(15) 0.0470(5) Uani 1 1 d . . .
H2D H 0.2997 -0.2056 0.2398 0.056 Uiso 1 1 calc R . .
C3 C 0.4350(3) -0.0448(2) 0.30633(13) 0.0411(5) Uani 1 1 d . . .
C4 C 0.4224(4) 0.0744(3) 0.34631(16) 0.0469(5) Uani 1 1 d . . .
H4 H 0.333(4) 0.115(3) 0.336(2) 0.048(8) Uiso 1 1 d . . .
C5 C 0.5629(4) 0.1320(2) 0.40997(16) 0.0502(6) Uani 1 1 d . . .
H5 H 0.548(4) 0.209(3) 0.436(2) 0.057(8) Uiso 1 1 d . . .
C6 C 0.7079(4) 0.0677(3) 0.43114(15) 0.0493(6) Uani 1 1 d . . .
F1 F 0.8476(3) 0.1227(2) 0.49338(11) 0.0754(6) Uani 1 1 d . . .
C7 C 0.7249(4) -0.0490(3) 0.3944(2) 0.0602(7) Uani 1 1 d . . .
H7 H 0.835(6) -0.096(4) 0.413(3) 0.097(13) Uiso 1 1 d . . .
C8 C 0.5861(4) -0.1050(3) 0.33080(18) 0.0527(6) Uani 1 1 d . . .
H8 H 0.599(5) -0.177(3) 0.297(2) 0.072(10) Uiso 1 1 d . . .
N2 N 0.7473(3) 0.40884(17) 0.11114(12) 0.0305(3) Uani 1 1 d . . .
H2A H 0.642(4) 0.365(2) 0.1159(18) 0.037(6) Uiso 1 1 d . . .
H2B H 0.795(4) 0.382(2) 0.0589(19) 0.040(6) Uiso 1 1 d . . .
H2C H 0.751(5) 0.486(3) 0.104(2) 0.063(9) Uiso 1 1 d . . .
C9 C 0.8753(3) 0.2544(2) 0.21377(17) 0.0378(4) Uani 1 1 d . . .
H9A H 0.751(4) 0.218(2) 0.2344(18) 0.041(6) Uiso 1 1 d . . .
H9B H 0.962(4) 0.247(3) 0.267(2) 0.052(8) Uiso 1 1 d . . .
H9C H 0.911(4) 0.209(3) 0.161(2) 0.048(7) Uiso 1 1 d . . .
C10 C 0.8829(3) 0.39437(18) 0.19205(14) 0.0317(4) Uani 1 1 d . . .
H10 H 1.008(3) 0.426(2) 0.1699(16) 0.032(6) Uiso 1 1 d . . .
C11 C 0.8410(3) 0.47099(19) 0.27653(14) 0.0383(4) Uani 1 1 d . . .
C12 C 0.6598(4) 0.4714(3) 0.30501(17) 0.0509(6) Uani 1 1 d . . .
H12 H 0.558(4) 0.423(3) 0.272(2) 0.048(7) Uiso 1 1 d . . .
C13 C 0.6274(6) 0.5374(3) 0.38671(19) 0.0678(9) Uani 1 1 d . . .
H13 H 0.504(5) 0.531(3) 0.403(2) 0.062(9) Uiso 1 1 d . . .
C14 C 0.7788(7) 0.6006(3) 0.43726(18) 0.0720(10) Uani 1 1 d . . .
F2 F 0.7472(4) 0.6639(2) 0.51794(13) 0.1038(9) Uani 1 1 d . . .
C15 C 0.9584(7) 0.6021(3) 0.4121(2) 0.0805(11) Uani 1 1 d . . .
H15 H 1.075(6) 0.657(4) 0.444(3) 0.093(12) Uiso 1 1 d . . .
C16 C 0.9913(5) 0.5376(3) 0.3290(2) 0.0662(8) Uani 1 1 d . . .
H16 H 1.136(6) 0.538(4) 0.306(3) 0.088(12) 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
Co1 Cl4 2.2556(5) . ?
Co1 Cl1 2.2689(5) . ?
Co1 Cl3 2.2706(5) . ?
Co1 Cl2 2.2827(5) . ?
N1 C2 1.492(3) . ?
N1 H1A 0.89(3) . ?
N1 H1B 0.83(3) . ?
N1 H1C 0.93(4) . ?
C1 C2 1.458(4) . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 H1F 0.9800 . ?
C2 C3 1.514(3) . ?
C2 H2D 1.0000 . ?
C3 C8 1.366(4) . ?
C3 C4 1.396(4) . ?
C4 C5 1.393(4) . ?
C4 H4 0.83(3) . ?
C5 C6 1.345(4) . ?
C5 H5 0.91(3) . ?
C6 C7 1.361(4) . ?
C6 F1 1.368(3) . ?
C7 C8 1.379(4) . ?
C7 H7 1.02(4) . ?
C8 H8 0.92(3) . ?
N2 C10 1.495(3) . ?
N2 H2A 0.83(3) . ?
N2 H2B 0.89(3) . ?
N2 H2C 0.82(3) . ?
C9 C10 1.512(3) . ?
C9 H9A 0.98(3) . ?
C9 H9B 0.96(3) . ?
C9 H9C 0.95(3) . ?
C10 C11 1.510(3) . ?
C10 H10 0.98(2) . ?
C11 C12 1.382(4) . ?
C11 C16 1.385(3) . ?
C12 C13 1.397(3) . ?
C12 H12 0.94(3) . ?
C13 C14 1.364(5) . ?
C13 H13 0.92(3) . ?
C14 C15 1.353(6) . ?
C14 F2 1.368(3) . ?
C15 C16 1.408(5) . ?
C15 H15 1.04(4) . ?
C16 H16 1.11(4) . ?

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
Cl4 Co1 Cl1 107.63(2) . . ?
Cl4 Co1 Cl3 112.47(2) . . ?
Cl1 Co1 Cl3 107.737(19) . . ?
Cl4 Co1 Cl2 109.02(2) . . ?
Cl1 Co1 Cl2 109.872(19) . . ?
Cl3 Co1 Cl2 110.058(19) . . ?
C2 N1 H1A 114.4(18) . . ?
C2 N1 H1B 114(2) . . ?
H1A N1 H1B 108(3) . . ?
C2 N1 H1C 110(2) . . ?
H1A N1 H1C 101(3) . . ?
H1B N1 H1C 109(3) . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C1 C2 N1 110.3(2) . . ?
C1 C2 C3 115.0(2) . . ?
N1 C2 C3 110.99(18) . . ?
C1 C2 H2D 106.7 . . ?
N1 C2 H2D 106.7 . . ?
C3 C2 H2D 106.7 . . ?
C8 C3 C4 119.3(2) . . ?
C8 C3 C2 117.9(2) . . ?
C4 C3 C2 122.8(2) . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 115(2) . . ?
C3 C4 H4 124(2) . . ?
C6 C5 C4 117.3(2) . . ?
C6 C5 H5 125(2) . . ?
C4 C5 H5 118(2) . . ?
C5 C6 C7 124.1(2) . . ?
C5 C6 F1 118.2(2) . . ?
C7 C6 F1 117.7(3) . . ?
C6 C7 C8 118.3(3) . . ?
C6 C7 H7 122(2) . . ?
C8 C7 H7 120(2) . . ?
C3 C8 C7 120.5(3) . . ?
C3 C8 H8 117(2) . . ?
C7 C8 H8 122(2) . . ?
C10 N2 H2A 113.3(18) . . ?
C10 N2 H2B 108.3(17) . . ?
H2A N2 H2B 107(2) . . ?
C10 N2 H2C 105(2) . . ?
H2A N2 H2C 118(3) . . ?
H2B N2 H2C 104(3) . . ?
C10 C9 H9A 111.7(15) . . ?
C10 C9 H9B 107.8(17) . . ?
H9A C9 H9B 106(2) . . ?
C10 C9 H9C 110.4(17) . . ?
H9A C9 H9C 112(2) . . ?
H9B C9 H9C 109(2) . . ?
N2 C10 C11 110.89(16) . . ?
N2 C10 C9 108.99(16) . . ?
C11 C10 C9 111.85(17) . . ?
N2 C10 H10 105.6(14) . . ?
C11 C10 H10 110.5(13) . . ?
C9 C10 H10 108.8(14) . . ?
C12 C11 C16 119.7(2) . . ?
C12 C11 C10 122.07(19) . . ?
C16 C11 C10 118.2(2) . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H12 120.0(17) . . ?
C13 C12 H12 119.4(17) . . ?
C14 C13 C12 118.3(3) . . ?
C14 C13 H13 126(2) . . ?
C12 C13 H13 116(2) . . ?
C15 C14 C13 123.1(3) . . ?
C15 C14 F2 118.6(3) . . ?
C13 C14 F2 118.3(4) . . ?
C14 C15 C16 118.7(3) . . ?
C14 C15 H15 125(2) . . ?
C16 C15 H15 116(2) . . ?
C11 C16 C15 119.7(4) . . ?
C11 C16 H16 119.9(19) . . ?
C15 C16 H16 120(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Cl2 0.89(3) 2.41(3) 3.2989(19) 171(2) .
N1 H1B Cl3 0.83(3) 2.63(3) 3.365(2) 148(3) 2
N1 H1B Cl4 0.83(3) 2.86(3) 3.2379(18) 110(3) .
N1 H1C Cl4 0.93(4) 2.43(4) 3.311(2) 160(3) 2_655
N1 H1C Cl1 0.93(4) 2.97(3) 3.465(2) 115(2) 2_655
N2 H2A Cl2 0.83(3) 2.42(3) 3.2534(19) 177(2) .
N2 H2B Cl3 0.89(3) 2.37(3) 3.2348(18) 165(2) 1_655
N2 H2B Cl1 0.89(3) 2.99(3) 3.4027(17) 110.2(19) .
N2 H2C Cl1 0.82(3) 2.67(3) 3.3076(19) 136(3) 2_665
N2 H2C Cl3 0.82(3) 2.71(3) 3.3563(19) 137(3) 2_665

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        33.73
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         1.571
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.077


