# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cocl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H4 Cl2 Co N2'
_chemical_formula_weight         209.92

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Cmmm

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

_cell_length_a                   12.0014(7)
_cell_length_b                   7.1040(4)
_cell_length_c                   3.5380(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     301.64(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    937
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      30.62

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             206
_exptl_absorpt_coefficient_mu    3.616
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5784
_exptl_absorpt_correction_T_max  0.9647
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1957
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.33
_diffrn_reflns_theta_max         30.67
_reflns_number_total             294
_reflns_number_gt                263
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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)+(0.0306P)²+0.6167P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         294
_refine_ls_number_parameters     18
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0654
_refine_ls_wR_factor_gt          0.0634
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_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 0.0000 1.0000 -0.5000 0.0102(2) Uani 1 8 d S . .
Cl1 Cl 0.14183(7) 1.0000 0.0000 0.0125(2) Uani 1 4 d S . .
N1 N 0.0000 0.6967(4) -0.5000 0.0114(6) Uani 1 4 d S . .
C1 C -0.0945(2) 0.5975(4) -0.5000 0.0222(7) Uani 1 2 d S . .
H1 H -0.1637 0.6625 -0.5000 0.027 Uiso 1 2 calc SR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.0128(3) 0.0050(3) 0.0126(4) 0.000 0.000 0.000
Cl1 0.0125(4) 0.0114(4) 0.0137(4) 0.000 0.000 0.000
N1 0.0142(13) 0.0071(13) 0.0128(15) 0.000 0.000 0.000
C1 0.0136(11) 0.0070(12) 0.046(2) 0.000 0.000 0.0013(9)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N1 2.154(3) 9_574 ?
Co1 N1 2.154(3) . ?
Co1 Cl1 2.4549(6) . ?
Co1 Cl1 2.4549(6) 9_574 ?
Co1 Cl1 2.4549(6) 1_554 ?
Co1 Cl1 2.4549(6) 9_575 ?
Cl1 Co1 2.4549(6) 1_556 ?
N1 C1 1.336(3) . ?
N1 C1 1.336(3) 11 ?
C1 C1 1.385(5) 3_564 ?
C1 H1 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
N1 Co1 N1 180.0 9_574 . ?
N1 Co1 Cl1 90.0 9_574 . ?
N1 Co1 Cl1 90.0 . . ?
N1 Co1 Cl1 90.0 9_574 9_574 ?
N1 Co1 Cl1 90.0 . 9_574 ?
Cl1 Co1 Cl1 180.0 . 9_574 ?
N1 Co1 Cl1 90.0 9_574 1_554 ?
N1 Co1 Cl1 90.0 . 1_554 ?
Cl1 Co1 Cl1 92.21(3) . 1_554 ?
Cl1 Co1 Cl1 87.79(3) 9_574 1_554 ?
N1 Co1 Cl1 90.0 9_574 9_575 ?
N1 Co1 Cl1 90.0 . 9_575 ?
Cl1 Co1 Cl1 87.79(3) . 9_575 ?
Cl1 Co1 Cl1 92.21(3) 9_574 9_575 ?
Cl1 Co1 Cl1 180.0 1_554 9_575 ?
Co1 Cl1 Co1 92.21(3) . 1_556 ?
C1 N1 C1 116.3(3) . 11 ?
C1 N1 Co1 121.85(15) . . ?
C1 N1 Co1 121.85(15) 11 . ?
N1 C1 C1 121.85(15) . 3_564 ?
N1 C1 H1 119.1 . . ?
C1 C1 H1 119.1 3_564 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Co1 Cl1 Co1 90.0 9_574 . . 1_556 ?
N1 Co1 Cl1 Co1 -90.0 . . . 1_556 ?
Cl1 Co1 Cl1 Co1 1.3 9_574 . . 1_556 ?
Cl1 Co1 Cl1 Co1 180.0 1_554 . . 1_556 ?
Cl1 Co1 Cl1 Co1 0.0 9_575 . . 1_556 ?
N1 Co1 N1 C1 0(100) 9_574 . . . ?
Cl1 Co1 N1 C1 133.896(14) . . . . ?
Cl1 Co1 N1 C1 -46.103(14) 9_574 . . . ?
Cl1 Co1 N1 C1 -133.897(14) 1_554 . . . ?
Cl1 Co1 N1 C1 46.103(14) 9_575 . . . ?
N1 Co1 N1 C1 0.0 9_574 . . 11 ?
Cl1 Co1 N1 C1 -46.104(14) . . . 11 ?
Cl1 Co1 N1 C1 133.897(14) 9_574 . . 11 ?
Cl1 Co1 N1 C1 46.103(14) 1_554 . . 11 ?
Cl1 Co1 N1 C1 -133.897(14) 9_575 . . 11 ?
C1 N1 C1 C1 0.0 11 . . 3_564 ?
Co1 N1 C1 C1 180.0 . . . 3_564 ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        30.67
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.128

_database_code_depnum_ccdc_archive 'CCDC 1012088'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_i-4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 Cl2 Co N4'
_chemical_formula_weight         290.01

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'
Co Co 0.3494 0.9721 '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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   I-4

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

_cell_length_a                   7.1489(6)
_cell_length_b                   7.1489(6)
_cell_length_c                   10.6653(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     545.07(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1919
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      33.46

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             290
_exptl_absorpt_coefficient_mu    2.033
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5998
_exptl_absorpt_correction_T_max  0.9605
_exptl_absorpt_process_details   Sadabs

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5529
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.43
_diffrn_reflns_theta_max         35.83
_reflns_number_total             1266
_reflns_number_gt                1016
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0341P)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   0.47(5)
_refine_ls_number_reflns         1266
_refine_ls_number_parameters     54
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0763
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

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 0.0000 0.0000 0.0000 0.01621(11) Uani 1 4 d S . .
Cl1 Cl 0.0000 0.0000 0.22550(4) 0.02640(14) Uani 1 2 d S . .
C1 C -0.1124(15) 0.4048(14) 0.0743(7) 0.027(2) Uani 0.50 1 d P . .
H1 H -0.1991 0.3405 0.1230 0.033 Uiso 0.50 1 calc PR . .
C2 C 0.1119(14) 0.4024(16) -0.0698(7) 0.029(2) Uani 0.50 1 d P . .
H2 H 0.2023 0.3385 -0.1156 0.034 Uiso 0.50 1 calc PR . .
C3 C 0.1063(12) 0.4041(11) 0.0839(6) 0.0170(14) Uani 0.50 1 d P . .
H3 H 0.1723 0.3423 0.1466 0.020 Uiso 0.50 1 calc PR . .
C4 C -0.1074(13) 0.4024(13) -0.0801(6) 0.0207(19) Uani 0.50 1 d P . .
H4 H -0.1782 0.3416 -0.1408 0.025 Uiso 0.50 1 calc PR . .
N1 N -0.00009(18) 0.30523(18) -0.0016(6) 0.0213(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.01287(13) 0.01287(13) 0.02288(19) 0.000 0.000 0.000
Cl1 0.0302(12) 0.0253(12) 0.0237(2) 0.000 0.000 -0.0064(11)
C1 0.032(5) 0.018(4) 0.032(5) 0.000(3) 0.010(3) -0.014(3)
C2 0.026(4) 0.029(4) 0.032(4) 0.000(3) 0.004(3) 0.015(3)
C3 0.026(3) 0.008(2) 0.016(2) 0.0000(16) -0.0126(19) -0.005(2)
C4 0.021(4) 0.017(4) 0.024(4) -0.002(3) -0.012(3) 0.008(3)
N1 0.0218(6) 0.0143(5) 0.0276(6) -0.006(2) 0.002(2) -0.0001(4)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N1 2.1821(13) 3 ?
Co1 N1 2.1821(13) 2 ?
Co1 N1 2.1821(13) . ?
Co1 N1 2.1821(13) 4 ?
Co1 Cl1 2.4050(6) 3 ?
Co1 Cl1 2.4050(6) . ?
C1 N1 1.344(10) . ?
C1 C3 1.371(12) 2_565 ?
C1 H1 0.9300 . ?
C2 N1 1.286(11) . ?
C2 C4 1.400(14) 2_565 ?
C2 H2 0.9300 . ?
C3 C1 1.371(12) 2_565 ?
C3 N1 1.382(8) . ?
C3 H3 0.9300 . ?
C4 N1 1.331(8) . ?
C4 C2 1.400(14) 2_565 ?
C4 H4 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
N1 Co1 N1 90.004(3) 3 2 ?
N1 Co1 N1 90.003(3) 3 . ?
N1 Co1 N1 179.1(3) 2 . ?
N1 Co1 N1 179.1(3) 3 4 ?
N1 Co1 N1 90.003(3) 2 4 ?
N1 Co1 N1 90.004(3) . 4 ?
N1 Co1 Cl1 90.45(16) 3 3 ?
N1 Co1 Cl1 89.55(16) 2 3 ?
N1 Co1 Cl1 89.55(16) . 3 ?
N1 Co1 Cl1 90.45(16) 4 3 ?
N1 Co1 Cl1 89.55(16) 3 . ?
N1 Co1 Cl1 90.45(16) 2 . ?
N1 Co1 Cl1 90.45(16) . . ?
N1 Co1 Cl1 89.55(16) 4 . ?
Cl1 Co1 Cl1 180.0 3 . ?
N1 C1 C3 123.6(7) . 2_565 ?
N1 C1 H1 118.2 . . ?
C3 C1 H1 118.2 2_565 . ?
N1 C2 C4 124.6(7) . 2_565 ?
N1 C2 H2 117.7 . . ?
C4 C2 H2 117.7 2_565 . ?
C1 C3 N1 118.6(6) 2_565 . ?
C1 C3 H3 120.7 2_565 . ?
N1 C3 H3 120.7 . . ?
N1 C4 C2 119.0(7) . 2_565 ?
N1 C4 H4 120.5 . . ?
C2 C4 H4 120.5 2_565 . ?
C2 N1 C4 73.8(6) . . ?
C2 N1 C1 115.3(6) . . ?
C4 N1 C1 76.0(3) . . ?
C2 N1 C3 75.8(3) . . ?
C4 N1 C3 117.7(5) . . ?
C1 N1 C3 70.2(6) . . ?
C2 N1 Co1 123.0(5) . . ?
C4 N1 Co1 121.8(5) . . ?
C1 N1 Co1 121.7(4) . . ?
C3 N1 Co1 120.4(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C2 N1 C4 57.5(8) 2_565 . . . ?
C4 C2 N1 C1 -7.9(10) 2_565 . . . ?
C4 C2 N1 C3 -67.4(8) 2_565 . . . ?
C4 C2 N1 Co1 175.3(6) 2_565 . . . ?
C2 C4 N1 C2 -65.8(8) 2_565 . . . ?
C2 C4 N1 C1 56.3(7) 2_565 . . . ?
C2 C4 N1 C3 -2.0(9) 2_565 . . . ?
C2 C4 N1 Co1 175.1(6) 2_565 . . . ?
C3 C1 N1 C2 -2.4(11) 2_565 . . . ?
C3 C1 N1 C4 -66.6(8) 2_565 . . . ?
C3 C1 N1 C3 60.2(8) 2_565 . . . ?
C3 C1 N1 Co1 174.4(6) 2_565 . . . ?
C1 C3 N1 C2 55.4(7) 2_565 . . . ?
C1 C3 N1 C4 -7.3(8) 2_565 . . . ?
C1 C3 N1 C1 -68.6(8) 2_565 . . . ?
C1 C3 N1 Co1 175.6(6) 2_565 . . . ?
N1 Co1 N1 C2 42.5(5) 3 . . . ?
N1 Co1 N1 C2 -47.9(6) 2 . . . ?
N1 Co1 N1 C2 -138.4(6) 4 . . . ?
Cl1 Co1 N1 C2 -48.0(6) 3 . . . ?
Cl1 Co1 N1 C2 132.0(6) . . . . ?
N1 Co1 N1 C4 133.1(6) 3 . . . ?
N1 Co1 N1 C4 42.7(5) 2 . . . ?
N1 Co1 N1 C4 -47.8(5) 4 . . . ?
Cl1 Co1 N1 C4 42.7(5) 3 . . . ?
Cl1 Co1 N1 C4 -137.3(5) . . . . ?
N1 Co1 N1 C1 -134.1(6) 3 . . . ?
N1 Co1 N1 C1 135.4(6) 2 . . . ?
N1 Co1 N1 C1 45.0(5) 4 . . . ?
Cl1 Co1 N1 C1 135.4(6) 3 . . . ?
Cl1 Co1 N1 C1 -44.6(6) . . . . ?
N1 Co1 N1 C3 -49.9(4) 3 . . . ?
N1 Co1 N1 C3 -140.3(5) 2 . . . ?
N1 Co1 N1 C3 129.2(5) 4 . . . ?
Cl1 Co1 N1 C3 -140.3(4) 3 . . . ?
Cl1 Co1 N1 C3 39.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        35.83
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         1.120
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.117
_database_code_depnum_ccdc_archive 'CCDC 1012089'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cocl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 Cl2 Co N4'
_chemical_formula_weight         290.01

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           Tetragonal
_symmetry_space_group_name_H-M   I-4

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

_cell_length_a                   7.1449(11)
_cell_length_b                   7.1449(11)
_cell_length_c                   10.633(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     542.83(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    214
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      21.35

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             290
_exptl_absorpt_coefficient_mu    2.042
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7917
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1015
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0944
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.44
_diffrn_reflns_theta_max         28.46
_reflns_number_total             663
_reflns_number_gt                431
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0258P)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   -0.02(19)
_refine_ls_number_reflns         663
_refine_ls_number_parameters     53
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0696
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.980
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

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 0.0000 0.0000 0.0000 0.0131(3) Uani 1 4 d S . .
Cl1 Cl 0.0000 0.0000 0.22619(13) 0.0203(4) Uani 1 2 d S . .
C1 C 0.121(3) 0.404(4) -0.075(3) 0.015(5) Uani 0.50 1 d PU . .
H1 H 0.2129 0.3407 -0.1234 0.018 Uiso 0.50 1 calc PR . .
C2 C -0.125(3) 0.404(3) 0.073(3) 0.027(6) Uani 0.50 1 d PU . .
H2 H -0.2255 0.3432 0.1155 0.032 Uiso 0.50 1 calc PR . .
C3 C -0.103(3) 0.400(3) -0.082(2) 0.006(3) Uani 0.50 1 d PU . .
H3 H -0.1641 0.3332 -0.1475 0.007 Uiso 0.50 1 calc PR . .
C4 C 0.102(3) 0.400(4) 0.080(3) 0.016(5) Uani 0.50 1 d PU . .
H4 H 0.1648 0.3347 0.1450 0.019 Uiso 0.50 1 calc PR . .
N1 N 0.0005(5) 0.3055(4) 0.004(2) 0.0147(9) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.0093(4) 0.0093(4) 0.0205(8) 0.000 0.000 0.000
Cl1 0.022(3) 0.019(3) 0.0195(9) 0.000 0.000 -0.007(3)
C1 0.012(6) 0.014(6) 0.019(6) -0.002(4) 0.005(4) -0.001(4)
C2 0.023(9) 0.021(7) 0.036(9) 0.002(5) -0.003(6) 0.002(6)
C3 0.007(4) 0.005(4) 0.006(4) 0.0007(19) 0.0002(19) -0.0004(19)
C4 0.014(6) 0.012(6) 0.021(7) 0.005(4) -0.003(4) 0.005(4)
N1 0.0162(16) 0.0085(15) 0.019(3) 0.000(7) 0.000(7) -0.0006(12)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N1 2.183(3) 3 ?
Co1 N1 2.183(3) . ?
Co1 N1 2.183(3) 4 ?
Co1 N1 2.183(3) 2 ?
Co1 Cl1 2.4051(14) 3 ?
Co1 Cl1 2.4051(14) . ?
C1 N1 1.39(3) . ?
C1 C3 1.41(3) 2_565 ?
C1 H1 0.9500 . ?
C2 N1 1.36(3) . ?
C2 C4 1.41(4) 2_565 ?
C2 H2 0.9500 . ?
C3 N1 1.35(2) . ?
C3 C1 1.41(3) 2_565 ?
C3 H3 0.9500 . ?
C4 N1 1.28(3) . ?
C4 C2 1.41(4) 2_565 ?
C4 C4 2.04(5) 2_565 ?
C4 H4 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
N1 Co1 N1 90.02(2) 3 . ?
N1 Co1 N1 178.0(12) 3 4 ?
N1 Co1 N1 90.02(2) . 4 ?
N1 Co1 N1 90.02(2) 3 2 ?
N1 Co1 N1 178.0(12) . 2 ?
N1 Co1 N1 90.02(2) 4 2 ?
N1 Co1 Cl1 89.0(6) 3 3 ?
N1 Co1 Cl1 91.0(6) . 3 ?
N1 Co1 Cl1 89.0(6) 4 3 ?
N1 Co1 Cl1 91.0(6) 2 3 ?
N1 Co1 Cl1 91.0(6) 3 . ?
N1 Co1 Cl1 89.0(6) . . ?
N1 Co1 Cl1 91.0(6) 4 . ?
N1 Co1 Cl1 89.0(6) 2 . ?
Cl1 Co1 Cl1 180.0 3 . ?
N1 C1 C3 119(2) . 2_565 ?
N1 C1 H1 120.7 . . ?
C3 C1 H1 120.7 2_565 . ?
N1 C2 C4 117(2) . 2_565 ?
N1 C2 H2 121.3 . . ?
C4 C2 H2 121.3 2_565 . ?
N1 C3 C1 121(2) . 2_565 ?
N1 C3 H3 119.6 . . ?
C1 C3 H3 119.6 2_565 . ?
N1 C4 C2 124(3) . 2_565 ?
N1 C4 C4 88.1(15) . 2_565 ?
C2 C4 C4 52.5(15) 2_565 2_565 ?
N1 C4 H4 118.0 . . ?
C2 C4 H4 118.0 2_565 . ?
C4 C4 H4 133.2 2_565 . ?
C4 N1 C3 118.1(16) . . ?
C4 N1 C2 75.9(17) . . ?
C3 N1 C2 75.3(7) . . ?
C4 N1 C1 76.4(6) . . ?
C3 N1 C1 71.3(16) . . ?
C2 N1 C1 118.2(17) . . ?
C4 N1 Co1 122.7(15) . . ?
C3 N1 Co1 119.1(13) . . ?
C2 N1 Co1 121.7(13) . . ?
C1 N1 Co1 119.8(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C4 N1 C3 -6(3) 2_565 . . . ?
C4 C4 N1 C3 35(2) 2_565 . . . ?
C2 C4 N1 C2 -70(3) 2_565 . . . ?
C4 C4 N1 C2 -29.6(15) 2_565 . . . ?
C2 C4 N1 C1 54(2) 2_565 . . . ?
C4 C4 N1 C1 94.6(18) 2_565 . . . ?
C2 C4 N1 Co1 170.7(17) 2_565 . . . ?
C4 C4 N1 Co1 -148.5(13) 2_565 . . . ?
C1 C3 N1 C4 -9(3) 2_565 . . . ?
C1 C3 N1 C2 55.4(18) 2_565 . . . ?
C1 C3 N1 C1 -72(2) 2_565 . . . ?
C1 C3 N1 Co1 173.8(16) 2_565 . . . ?
C4 C2 N1 C4 53(2) 2_565 . . . ?
C4 C2 N1 C3 -71(2) 2_565 . . . ?
C4 C2 N1 C1 -12(3) 2_565 . . . ?
C4 C2 N1 Co1 173.5(17) 2_565 . . . ?
C3 C1 N1 C4 -67(2) 2_565 . . . ?
C3 C1 N1 C3 59(2) 2_565 . . . ?
C3 C1 N1 C2 -2(3) 2_565 . . . ?
C3 C1 N1 Co1 172.5(16) 2_565 . . . ?
N1 Co1 N1 C4 -48.9(15) 3 . . . ?
N1 Co1 N1 C4 133(2) 4 . . . ?
N1 Co1 N1 C4 42.1(18) 2 . . . ?
Cl1 Co1 N1 C4 -137.9(18) 3 . . . ?
Cl1 Co1 N1 C4 42.1(18) . . . . ?
N1 Co1 N1 C3 127.7(18) 3 . . . ?
N1 Co1 N1 C3 -50.3(11) 4 . . . ?
N1 Co1 N1 C3 -141.3(14) 2 . . . ?
Cl1 Co1 N1 C3 38.7(13) 3 . . . ?
Cl1 Co1 N1 C3 -141.3(13) . . . . ?
N1 Co1 N1 C2 -142(2) 3 . . . ?
N1 Co1 N1 C2 39.9(13) 4 . . . ?
N1 Co1 N1 C2 -51.1(16) 2 . . . ?
Cl1 Co1 N1 C2 128.9(16) 3 . . . ?
Cl1 Co1 N1 C2 -51.1(16) . . . . ?
N1 Co1 N1 C1 43.8(13) 3 . . . ?
N1 Co1 N1 C1 -134(2) 4 . . . ?
N1 Co1 N1 C1 134.8(16) 2 . . . ?
Cl1 Co1 N1 C1 -45.2(16) 3 . . . ?
Cl1 Co1 N1 C1 134.8(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        28.46
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.105
_database_code_depnum_ccdc_archive 'CCDC 1012090'
