# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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 
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data_[Co2LI2(OH)]I
_database_code_depnum_ccdc_archive 'CCDC 985972'
_audit_update_record             
;
2015-01-23 deposited with the CCDC.
2015-01-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H33 Co2 I2 N4 O, I'
_chemical_formula_sum            'C22 H33 Co2 I3 N4 O'
_chemical_formula_weight         868.08

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.6864(3)
_cell_length_b                   17.6541(4)
_cell_length_c                   14.7499(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.1520(10)
_cell_angle_gamma                90
_cell_volume                     2798.02(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9921
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      35.0

_exptl_crystal_description       'triangular prism'
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.061
_exptl_crystal_F_000             1656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_absorpt_coefficient_mu    4.517
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
SADABS;Sheldrick1996;Blessing,ActaC.1995,A51,33
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector Smart6000'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42895
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.894
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6770
_reflns_number_gt                6325
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Hydrogen atoms bonded to carbon atoms were calculated on idealized position and
included in the refinement with Uiso constrained to the Ueq of the bonding carbon atom. 
Hydrogen atoms bonded to nitrogen and oxygen were located from Difference Fourier 
Syntheses and refined with bonding re/constraints (SADI, DFIX) and their 
Uisos constrained to Ueq of the bonding atom.
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART, 1997'
_computing_cell_refinement       'Bruker SAINT, V6.45A, 2003 '
_computing_data_reduction        'Bruker SAINT, V6.45A, 2003'
_computing_structure_solution    'Bruker SHELXTL 6.14, 1998'
_computing_molecular_graphics    'Diamond 2.0'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0111P)²+18.3752P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6770
_refine_ls_number_parameters     313
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.0939
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.272
_refine_ls_restrained_S_all      1.271
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.06615(7) 0.60100(4) 0.26177(6) 0.02767(16) Uani 1 1 d . . . . .
Co2 Co -0.17795(6) 0.68069(4) 0.31073(5) 0.01963(14) Uani 1 1 d . . . . .
I1 I 0.12613(3) 0.57816(2) 0.45530(3) 0.03201(9) Uani 1 1 d . . . . .
I2 I -0.38381(3) 0.74883(2) 0.20084(3) 0.03660(11) Uani 1 1 d . . . . .
I3A I 0.02171(5) 0.36073(3) -0.01672(3) 0.03460(11) Uani 0.9 1 d . . P A 1
I3B I -0.0362(5) 0.3486(3) -0.0049(4) 0.0533(14) Uani 0.1 1 d . . P B 3
O1 O -0.0887(3) 0.6530(2) 0.2318(3) 0.0216(7) Uani 1 1 d D . . . .
H1O H -0.122(5) 0.663(3) 0.1706(17) 0.026 Uiso 1 1 d D U . . .
N1 N 0.0823(4) 0.4963(3) 0.2069(3) 0.0262(9) Uani 1 1 d D . . . .
H1N H 0.060(6) 0.503(4) 0.147(3) 0.031 Uiso 1 1 d D U . . .
N2 N 0.2234(4) 0.6504(3) 0.2556(4) 0.0294(10) Uani 1 1 d D . . . .
H2N H 0.189(6) 0.661(4) 0.197(3) 0.035 Uiso 1 1 d D U . . .
N3 N -0.0990(4) 0.7517(2) 0.4298(3) 0.0232(9) Uani 1 1 d D . . . .
H3N H -0.032(4) 0.732(3) 0.462(4) 0.028 Uiso 1 1 d D U . . .
N4 N -0.2396(4) 0.5976(2) 0.3800(3) 0.0220(8) Uani 1 1 d D . . . .
H4N H -0.178(4) 0.573(3) 0.413(4) 0.026 Uiso 1 1 d D U . . .
C1 C 0.2129(5) 0.4701(3) 0.2410(4) 0.0306(12) Uani 1 1 d . . . . .
H1A H 0.2147 0.4206 0.2102 0.037 Uiso 1 1 calc R U . . .
H1B H 0.2463 0.4626 0.3133 0.037 Uiso 1 1 calc R U . . .
C2 C 0.2962(5) 0.5255(4) 0.2162(5) 0.0367(13) Uani 1 1 d . . . . .
H2A H 0.2543 0.5399 0.1459 0.044 Uiso 1 1 calc R U . . .
H2B H 0.3744 0.4991 0.2243 0.044 Uiso 1 1 calc R U . . .
C3 C 0.3294(5) 0.5980(4) 0.2784(5) 0.0364(13) Uani 1 1 d . . . . .
H3A H 0.3605 0.5841 0.3491 0.044 Uiso 1 1 calc R U . . .
H3B H 0.3975 0.6244 0.2673 0.044 Uiso 1 1 calc R U . . .
C4 C 0.2640(5) 0.7241(3) 0.3072(5) 0.0381(14) Uani 1 1 d . . . . .
H4A H 0.3252 0.7483 0.2854 0.046 Uiso 1 1 calc R U . . .
H4B H 0.3047 0.7155 0.3792 0.046 Uiso 1 1 calc R U . . .
C5 C 0.1532(5) 0.7752(3) 0.2847(5) 0.0332(13) Uani 1 1 d . . . . .
C6 C 0.0905(6) 0.8039(3) 0.1908(5) 0.0377(14) Uani 1 1 d . . . . .
H6A H 0.1247 0.7970 0.1426 0.045 Uiso 1 1 calc R U . . .
C7 C -0.0206(6) 0.8423(3) 0.1655(5) 0.0395(14) Uani 1 1 d . . . . .
H7A H -0.0618 0.8626 0.1011 0.047 Uiso 1 1 calc R U . . .
C8 C -0.0712(6) 0.8509(3) 0.2355(5) 0.0343(13) Uani 1 1 d . . . . .
H8A H -0.1495 0.8752 0.2180 0.041 Uiso 1 1 calc R U . . .
C9 C -0.0090(5) 0.8246(3) 0.3305(4) 0.0278(11) Uani 1 1 d . . . . .
C10 C 0.1054(5) 0.7877(3) 0.3559(4) 0.0296(11) Uani 1 1 d . . . . .
H10A H 0.1502 0.7713 0.4218 0.036 Uiso 1 1 calc R U . . .
C11 C -0.0689(5) 0.8292(3) 0.4038(4) 0.0300(12) Uani 1 1 d . . . . .
H11A H -0.0118 0.8550 0.4642 0.036 Uiso 1 1 calc R U . . .
H11B H -0.1462 0.8595 0.3756 0.036 Uiso 1 1 calc R U . . .
C12 C -0.1775(5) 0.7572(3) 0.4883(4) 0.0293(11) Uani 1 1 d . . . . .
H12A H -0.2597 0.7786 0.4464 0.035 Uiso 1 1 calc R U . . .
H12B H -0.1375 0.7921 0.5445 0.035 Uiso 1 1 calc R U . . .
C13 C -0.1960(5) 0.6806(4) 0.5270(4) 0.0326(12) Uani 1 1 d . . . . .
H13A H -0.1145 0.6545 0.5550 0.039 Uiso 1 1 calc R U . . .
H13B H -0.2240 0.6888 0.5815 0.039 Uiso 1 1 calc R U . . .
C14 C -0.2886(5) 0.6286(3) 0.4517(4) 0.0297(11) Uani 1 1 d . . . . .
H14A H -0.3092 0.5861 0.4863 0.036 Uiso 1 1 calc R U . . .
H14B H -0.3662 0.6571 0.4153 0.036 Uiso 1 1 calc R U . . .
C15 C -0.3327(5) 0.5455(3) 0.3100(4) 0.0259(10) Uani 1 1 d . . . . .
H15A H -0.4135 0.5720 0.2790 0.031 Uiso 1 1 calc R U . . .
H15B H -0.3447 0.5012 0.3464 0.031 Uiso 1 1 calc R U . . .
C16 C -0.2911(5) 0.5191(3) 0.2318(4) 0.0241(10) Uani 1 1 d . . . . .
C17 C -0.3606(5) 0.5336(3) 0.1326(4) 0.0270(11) Uani 1 1 d . . . . .
H17A H -0.4392 0.5578 0.1131 0.032 Uiso 1 1 calc R U . . .
C18 C -0.3162(5) 0.5130(3) 0.0619(4) 0.0307(12) Uani 1 1 d . . . . .
H18A H -0.3656 0.5219 -0.0058 0.037 Uiso 1 1 calc R U . . .
C19 C -0.1996(5) 0.4793(3) 0.0893(4) 0.0268(11) Uani 1 1 d . . . . .
H19A H -0.1686 0.4662 0.0407 0.032 Uiso 1 1 calc R U . . .
C20 C -0.1286(5) 0.4648(3) 0.1890(4) 0.0237(10) Uani 1 1 d . . . . .
C21 C -0.1756(5) 0.4832(3) 0.2591(4) 0.0225(10) Uani 1 1 d . . . . .
H21A H -0.1289 0.4712 0.3265 0.027 Uiso 1 1 calc R U . . .
C22 C 0.0025(5) 0.4361(3) 0.2214(4) 0.0273(11) Uani 1 1 d . . . . .
H22A H 0.0345 0.4215 0.2918 0.033 Uiso 1 1 calc R U . . .
H22B H 0.0042 0.3908 0.1823 0.033 Uiso 1 1 calc R U . . .


_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 O1 1.919(3) . ?
Co1 N1 2.055(5) . ?
Co1 N2 2.068(5) . ?
Co1 I1 2.6887(9) . ?
Co1 Co2 3.5013(10) . ?
Co2 O1 1.907(4) . ?
Co2 N3 2.057(4) . ?
Co2 N4 2.071(4) . ?
Co2 I2 2.6068(7) . ?
O1 H1O 0.848(19) . ?
N1 C1 1.481(7) . ?
N1 C22 1.483(7) . ?
N1 H1N 0.82(3) . ?
N2 C3 1.475(7) . ?
N2 C4 1.488(7) . ?
N2 H2N 0.82(4) . ?
N3 C12 1.489(7) . ?
N3 C11 1.500(7) . ?
N3 H3N 0.82(4) . ?
N4 C15 1.488(6) . ?
N4 C14 1.491(7) . ?
N4 H4N 0.81(4) . ?
C1 C2 1.523(8) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.533(9) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.506(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.384(9) . ?
C5 C10 1.388(9) . ?
C6 C7 1.380(9) . ?
C6 H6A 0.9500 . ?
C7 C8 1.385(9) . ?
C7 H7A 0.9500 . ?
C8 C9 1.380(8) . ?
C8 H8A 0.9500 . ?
C9 C10 1.399(8) . ?
C9 C11 1.503(8) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.517(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.517(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.491(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.389(7) . ?
C16 C21 1.400(7) . ?
C17 C18 1.383(8) . ?
C17 H17A 0.9500 . ?
C18 C19 1.393(8) . ?
C18 H18A 0.9500 . ?
C19 C20 1.400(7) . ?
C19 H19A 0.9500 . ?
C20 C21 1.386(7) . ?
C20 C22 1.503(7) . ?
C21 H21A 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?

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
O1 Co1 N1 124.30(16) . . ?
O1 Co1 N2 124.19(17) . . ?
N1 Co1 N2 98.09(19) . . ?
O1 Co1 I1 98.32(11) . . ?
N1 Co1 I1 104.90(13) . . ?
N2 Co1 I1 104.18(14) . . ?
O1 Co1 Co2 23.71(11) . . ?
N1 Co1 Co2 130.60(13) . . ?
N2 Co1 Co2 130.54(13) . . ?
I1 Co1 Co2 74.61(2) . . ?
O1 Co2 N3 120.54(16) . . ?
O1 Co2 N4 119.92(16) . . ?
N3 Co2 N4 97.84(17) . . ?
O1 Co2 I2 109.36(11) . . ?
N3 Co2 I2 104.13(12) . . ?
N4 Co2 I2 102.63(12) . . ?
O1 Co2 Co1 23.86(10) . . ?
N3 Co2 Co1 107.03(12) . . ?
N4 Co2 Co1 106.65(12) . . ?
I2 Co2 Co1 133.22(3) . . ?
Co2 O1 Co1 132.43(19) . . ?
Co2 O1 H1O 118(4) . . ?
Co1 O1 H1O 110(4) . . ?
C1 N1 C22 110.4(4) . . ?
C1 N1 Co1 112.9(3) . . ?
C22 N1 Co1 115.3(3) . . ?
C1 N1 H1N 105(5) . . ?
C22 N1 H1N 107(5) . . ?
Co1 N1 H1N 105(5) . . ?
C3 N2 C4 111.1(4) . . ?
C3 N2 Co1 114.0(4) . . ?
C4 N2 Co1 117.1(4) . . ?
C3 N2 H2N 114(5) . . ?
C4 N2 H2N 105(5) . . ?
Co1 N2 H2N 94(5) . . ?
C12 N3 C11 110.4(4) . . ?
C12 N3 Co2 111.3(3) . . ?
C11 N3 Co2 114.1(3) . . ?
C12 N3 H3N 112(4) . . ?
C11 N3 H3N 105(4) . . ?
Co2 N3 H3N 104(4) . . ?
C15 N4 C14 109.8(4) . . ?
C15 N4 Co2 113.4(3) . . ?
C14 N4 Co2 113.2(3) . . ?
C15 N4 H4N 109(4) . . ?
C14 N4 H4N 105(4) . . ?
Co2 N4 H4N 106(4) . . ?
N1 C1 C2 112.9(5) . . ?
N1 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C1 C2 C3 115.3(5) . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
N2 C3 C2 113.2(5) . . ?
N2 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
N2 C3 H3B 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
N2 C4 C5 109.7(5) . . ?
N2 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
N2 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C6 C5 C10 119.2(5) . . ?
C6 C5 C4 120.7(6) . . ?
C10 C5 C4 119.7(6) . . ?
C7 C6 C5 121.4(6) . . ?
C7 C6 H6A 119.3 . . ?
C5 C6 H6A 119.3 . . ?
C6 C7 C8 119.0(6) . . ?
C6 C7 H7A 120.5 . . ?
C8 C7 H7A 120.5 . . ?
C9 C8 C7 120.7(6) . . ?
C9 C8 H8A 119.6 . . ?
C7 C8 H8A 119.6 . . ?
C8 C9 C10 119.7(6) . . ?
C8 C9 C11 120.2(5) . . ?
C10 C9 C11 119.8(5) . . ?
C5 C10 C9 119.8(5) . . ?
C5 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
N3 C11 C9 111.0(4) . . ?
N3 C11 H11A 109.4 . . ?
C9 C11 H11A 109.4 . . ?
N3 C11 H11B 109.4 . . ?
C9 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N3 C12 C13 111.8(4) . . ?
N3 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
N3 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 115.4(5) . . ?
C14 C13 H13A 108.4 . . ?
C12 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
C12 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
N4 C14 C13 112.3(4) . . ?
N4 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
N4 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
N4 C15 C16 110.9(4) . . ?
N4 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
N4 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C21 119.0(5) . . ?
C17 C16 C15 121.6(5) . . ?
C21 C16 C15 119.3(5) . . ?
C18 C17 C16 120.5(5) . . ?
C18 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
C17 C18 C19 120.5(5) . . ?
C17 C18 H18A 119.7 . . ?
C19 C18 H18A 119.7 . . ?
C18 C19 C20 119.4(5) . . ?
C18 C19 H19A 120.3 . . ?
C20 C19 H19A 120.3 . . ?
C21 C20 C19 119.8(5) . . ?
C21 C20 C22 119.7(5) . . ?
C19 C20 C22 120.3(5) . . ?
C20 C21 C16 120.7(5) . . ?
C20 C21 H21A 119.7 . . ?
C16 C21 H21A 119.7 . . ?
N1 C22 C20 109.5(4) . . ?
N1 C22 H22A 109.8 . . ?
C20 C22 H22A 109.8 . . ?
N1 C22 H22B 109.8 . . ?
C20 C22 H22B 109.8 . . ?
H22A C22 H22B 108.2 . . ?

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
O1 H1O I3A 0.848(19) 2.96(5) 3.562(4) 129(5) 3_565
N1 H1N I3A 0.82(3) 3.00(5) 3.610(5) 133(5) 3_565
N2 H2N I3A 0.82(4) 2.85(5) 3.566(5) 147(6) 3_565
N3 H3N I2 0.82(4) 3.28(5) 3.795(4) 124(5) 4_676
N4 H4N I1 0.81(4) 3.22(5) 3.842(4) 136(5) 3_566
N1 H1N I3B 0.82(3) 3.30(5) 3.924(8) 134(5) 3_565
N2 H2N I3B 0.82(4) 2.70(4) 3.477(8) 160(6) 3_565
N3 H3N I1 0.82(4) 3.31(5) 3.959(4) 139(5) .
N4 H4N I1 0.81(4) 3.36(5) 3.985(4) 136(5) .
N1 H1N I3A 0.82(3) 3.39(6) 3.909(5) 124(5) .
N1 H1N I3B 0.82(3) 3.42(6) 3.884(7) 119(5) .

_refine_diff_density_max         2.842
_refine_diff_density_min         -1.180
_refine_diff_density_rms         0.144

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 985973'
_audit_update_record             
;
2015-01-23 deposited with the CCDC.
2015-01-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '[C22 H34 Cl2 Co N4][Cl]2'
_chemical_formula_sum            'C22 H34 Cl4 Co N4'
_chemical_formula_weight         555.26

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.8736(2)
_cell_length_b                   13.6929(3)
_cell_length_c                   21.0647(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2559.47(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    3978
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      24.5

_exptl_crystal_description       orthorhombic
_exptl_crystal_colour            'dark blue'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1156
_exptl_absorpt_coefficient_mu    1.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.567
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
SADABS;Sheldrick1996;Blessing,ActaC.1995,A51,33

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector Smart6000'
_diffrn_measurement_method       omega-scan

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20953
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.774
_diffrn_reflns_theta_max         33.449
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9030
_reflns_number_gt                6803
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_max     0.866
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;

Hydrogen atoms bonded to carbon-atoms were calculated on idealized positions 
and included in the refinement with Uiso constrained to the Ueq of the bonding 
carbon-atom. Hydrogen atoms bonded the nitrogen atoms were located from 
Difference-Fourier Syntheses and refined using N-H distance restraints (SADI). 

 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART, 1997'
_computing_cell_refinement       'Bruker SAINT, V6.45A, 2003 '
_computing_data_reduction        'Bruker SAINT, V6.45A, 2003'
_computing_structure_solution    'Bruker SHELXTL 6.14, 1998'
_computing_molecular_graphics    'Diamond 2.0'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0687P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2338 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(8)
_chemical_absolute_configuration R,S
_refine_ls_number_reflns         9030
_refine_ls_number_parameters     304
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.024
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.84017(6) -0.52086(5) -0.19090(3) 0.02882(15) Uani 1 1 d . . . . .
C1 C 1.1280(5) -0.5548(4) -0.1269(2) 0.0364(11) Uani 1 1 d . . . . .
H1B H 1.1413 -0.6125 -0.1547 0.044 Uiso 1 1 calc R U . . .
H1A H 1.1871 -0.5661 -0.0877 0.044 Uiso 1 1 calc R U . . .
Cl1 Cl 0.87915(12) -0.65051(9) -0.25701(6) 0.0417(3) Uani 1 1 d . . . . .
Cl2 Cl 0.59666(10) -0.48942(8) -0.17708(4) 0.0286(2) Uani 1 1 d . . . . .
C2 C 1.1895(5) -0.4651(4) -0.1607(3) 0.0427(12) Uani 1 1 d . . . . .
H2A H 1.1622 -0.4069 -0.1353 0.051 Uiso 1 1 calc R U . . .
H2B H 1.3008 -0.4696 -0.1610 0.051 Uiso 1 1 calc R U . . .
C22 C 0.9199(5) -0.6283(3) -0.0692(2) 0.0327(10) Uani 1 1 d . . . . .
H22B H 0.9909 -0.6329 -0.0331 0.039 Uiso 1 1 calc R U . . .
H22A H 0.9282 -0.6894 -0.0941 0.039 Uiso 1 1 calc R U . . .
C21 C 0.7215(5) -0.5408(3) -0.00499(19) 0.0265(9) Uani 1 1 d . . . . .
H21A H 0.7947 -0.4927 0.0054 0.032 Uiso 1 1 calc R U . . .
C20 C 0.7621(5) -0.6196(3) -0.04381(19) 0.0282(9) Uani 1 1 d . . . . .
Cl3 Cl 0.60926(12) -0.03369(8) -0.04235(5) 0.0338(2) Uani 1 1 d . . . . .
C3 C 1.1368(5) -0.4487(4) -0.2281(3) 0.0401(12) Uani 1 1 d . . . . .
H3A H 1.2011 -0.3983 -0.2482 0.048 Uiso 1 1 calc R U . . .
H3B H 1.1490 -0.5100 -0.2525 0.048 Uiso 1 1 calc R U . . .
Cl4 Cl 0.36640(13) -0.19701(8) 0.10217(5) 0.0338(2) Uani 1 1 d . . . . .
C4 C 0.9355(6) -0.3869(4) -0.2969(2) 0.0391(11) Uani 1 1 d . . . . .
H4A H 0.9413 -0.4440 -0.3255 0.047 Uiso 1 1 calc R U . . .
H4B H 1.0081 -0.3373 -0.3122 0.047 Uiso 1 1 calc R U . . .
N1 N 0.9647(4) -0.5453(3) -0.10991(18) 0.0282(8) Uani 1 1 d D . . . .
N2 N 0.9774(4) -0.4172(3) -0.23137(19) 0.0310(8) Uani 1 1 d D . . . .
N3 N 0.5529(4) -0.1925(3) -0.14418(17) 0.0270(7) Uani 1 1 d D . . . .
N4 N 0.4291(4) -0.3777(3) 0.02387(16) 0.0243(7) Uani 1 1 d D . . . .
C5 C 0.7800(5) -0.3454(4) -0.29887(19) 0.0312(10) Uani 1 1 d . . . . .
C19 C 0.6529(5) -0.6885(3) -0.0576(2) 0.0339(10) Uani 1 1 d . . . . .
H19A H 0.6784 -0.7425 -0.0838 0.041 Uiso 1 1 calc R U . . .
C6 C 0.6654(6) -0.3873(4) -0.3341(2) 0.0362(10) Uani 1 1 d . . . . .
H6A H 0.6866 -0.4425 -0.3599 0.043 Uiso 1 1 calc R U . . .
C18 C 0.5084(6) -0.6810(3) -0.0345(2) 0.0363(11) Uani 1 1 d . . . . .
H18A H 0.4356 -0.7293 -0.0449 0.044 Uiso 1 1 calc R U . . .
C7 C 0.5222(6) -0.3506(4) -0.3323(2) 0.0372(11) Uani 1 1 d . . . . .
H7A H 0.4456 -0.3796 -0.3576 0.045 Uiso 1 1 calc R U . . .
C17 C 0.4692(5) -0.6031(4) 0.0037(2) 0.0342(10) Uani 1 1 d . . . . .
H17A H 0.3697 -0.5981 0.0200 0.041 Uiso 1 1 calc R U . . .
C8 C 0.4875(6) -0.2704(4) -0.2935(2) 0.0338(10) Uani 1 1 d . . . . .
H8A H 0.3878 -0.2452 -0.2921 0.041 Uiso 1 1 calc R U . . .
C16 C 0.5763(5) -0.5318(3) 0.01842(19) 0.0282(8) Uani 1 1 d . . . . .
C9 C 0.6007(5) -0.2285(3) -0.25717(18) 0.0272(8) Uani 1 1 d . . . . .
C10 C 0.7472(5) -0.2644(3) -0.26173(19) 0.0281(9) Uani 1 1 d . . . . .
H10A H 0.8259 -0.2329 -0.2390 0.034 Uiso 1 1 calc R U . . .
C14 C 0.4846(5) -0.3460(3) -0.03965(19) 0.0276(8) Uani 1 1 d . . . . .
H14A H 0.4896 -0.4028 -0.0686 0.033 Uiso 1 1 calc R U . . .
H14B H 0.5872 -0.3183 -0.0356 0.033 Uiso 1 1 calc R U . . .
C11 C 0.5688(5) -0.1489(3) -0.21002(18) 0.0286(9) Uani 1 1 d . . . . .
H11A H 0.4746 -0.1146 -0.2218 0.034 Uiso 1 1 calc R U . . .
H11B H 0.6520 -0.1007 -0.2103 0.034 Uiso 1 1 calc R U . . .
C13 C 0.3781(5) -0.2691(3) -0.06692(18) 0.0289(9) Uani 1 1 d . . . . .
H13A H 0.2731 -0.2926 -0.0626 0.035 Uiso 1 1 calc R U . . .
H13B H 0.3878 -0.2083 -0.0418 0.035 Uiso 1 1 calc R U . . .
C12 C 0.4091(5) -0.2464(3) -0.13620(19) 0.0310(9) Uani 1 1 d . . . . .
H12A H 0.4137 -0.3081 -0.1606 0.037 Uiso 1 1 calc R U . . .
H12B H 0.3254 -0.2067 -0.1535 0.037 Uiso 1 1 calc R U . . .
C15 C 0.5357(5) -0.4445(3) 0.05765(19) 0.0299(9) Uani 1 1 d . . . . .
H15A H 0.4889 -0.4666 0.0978 0.036 Uiso 1 1 calc R U . . .
H15B H 0.6287 -0.4081 0.0684 0.036 Uiso 1 1 calc R U . . .
H4NA H 0.338(4) -0.402(3) 0.024(2) 0.020(11) Uiso 1 1 d D . . . .
H4NB H 0.411(5) -0.326(3) 0.0478(19) 0.028(12) Uiso 1 1 d D . . . .
H3NA H 0.635(4) -0.226(3) -0.136(2) 0.022(11) Uiso 1 1 d D . . . .
H3NB H 0.552(7) -0.142(3) -0.118(2) 0.048(17) Uiso 1 1 d D . . . .
H1N H 0.958(5) -0.488(3) -0.0891(18) 0.016(10) Uiso 1 1 d D . . . .
H2N H 0.975(6) -0.369(3) -0.204(2) 0.030(13) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N2 2.055(4) . ?
Co1 N1 2.060(4) . ?
Co1 Cl2 2.2224(11) . ?
Co1 Cl1 2.2827(13) . ?
C1 N1 1.498(5) . ?
C1 C2 1.520(8) . ?
C1 H1B 0.9900 . ?
C1 H1A 0.9900 . ?
C2 C3 1.513(8) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C22 N1 1.478(6) . ?
C22 C20 1.504(6) . ?
C22 H22B 0.9900 . ?
C22 H22A 0.9900 . ?
C21 C16 1.385(6) . ?
C21 C20 1.402(6) . ?
C21 H21A 0.9500 . ?
C20 C19 1.383(6) . ?
Cl3 H3NB 2.24(3) . ?
Cl3 H4NA 2.24(3) 4_545 ?
C3 N2 1.481(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
Cl4 H4NB 2.14(3) . ?
Cl4 H3NA 2.42(3) 4_445 ?
C4 N2 1.488(6) . ?
C4 C5 1.493(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
N1 H1N 0.90(4) . ?
N2 H2N 0.89(4) . ?
N3 C12 1.483(6) . ?
N3 C11 1.517(5) . ?
N3 H3NA 0.88(3) . ?
N3 H3NB 0.88(3) . ?
N4 C14 1.491(5) . ?
N4 C15 1.496(5) . ?
N4 H4NA 0.88(3) . ?
N4 H4NB 0.89(3) . ?
C5 C6 1.383(7) . ?
C5 C10 1.388(6) . ?
C19 C18 1.375(7) . ?
C19 H19A 0.9500 . ?
C6 C7 1.367(7) . ?
C6 H6A 0.9500 . ?
C18 C17 1.381(7) . ?
C18 H18A 0.9500 . ?
C7 C8 1.404(7) . ?
C7 H7A 0.9500 . ?
C17 C16 1.397(7) . ?
C17 H17A 0.9500 . ?
C8 C9 1.387(6) . ?
C8 H8A 0.9500 . ?
C16 C15 1.497(6) . ?
C9 C10 1.393(6) . ?
C9 C11 1.502(6) . ?
C10 H10A 0.9500 . ?
C14 C13 1.526(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 C12 1.517(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Co1 N1 97.93(16) . . ?
N2 Co1 Cl2 119.77(11) . . ?
N1 Co1 Cl2 116.40(10) . . ?
N2 Co1 Cl1 101.21(11) . . ?
N1 Co1 Cl1 107.31(11) . . ?
Cl2 Co1 Cl1 112.20(5) . . ?
N1 C1 C2 112.8(4) . . ?
N1 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 . . ?
N1 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
H1B C1 H1A 107.8 . . ?
C3 C2 C1 116.7(4) . . ?
C3 C2 H2A 108.1 . . ?
C1 C2 H2A 108.1 . . ?
C3 C2 H2B 108.1 . . ?
C1 C2 H2B 108.1 . . ?
H2A C2 H2B 107.3 . . ?
N1 C22 C20 113.3(4) . . ?
N1 C22 H22B 108.9 . . ?
C20 C22 H22B 108.9 . . ?
N1 C22 H22A 108.9 . . ?
C20 C22 H22A 108.9 . . ?
H22B C22 H22A 107.7 . . ?
C16 C21 C20 121.0(4) . . ?
C16 C21 H21A 119.5 . . ?
C20 C21 H21A 119.5 . . ?
C19 C20 C21 117.9(4) . . ?
C19 C20 C22 121.6(4) . . ?
C21 C20 C22 120.5(4) . . ?
H3NB Cl3 H4NA 94.0(19) . 4_545 ?
N2 C3 C2 112.4(4) . . ?
N2 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
N2 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
H4NB Cl4 H3NA 87.4(17) . 4_445 ?
N2 C4 C5 111.3(4) . . ?
N2 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C22 N1 C1 109.4(4) . . ?
C22 N1 Co1 117.4(3) . . ?
C1 N1 Co1 109.6(3) . . ?
C22 N1 H1N 112(3) . . ?
C1 N1 H1N 105(3) . . ?
Co1 N1 H1N 103(3) . . ?
C3 N2 C4 111.3(4) . . ?
C3 N2 Co1 110.2(3) . . ?
C4 N2 Co1 115.4(3) . . ?
C3 N2 H2N 102(3) . . ?
C4 N2 H2N 113(3) . . ?
Co1 N2 H2N 103(3) . . ?
C12 N3 C11 112.3(3) . . ?
C12 N3 H3NA 115(3) . . ?
C11 N3 H3NA 109(3) . . ?
C12 N3 H3NB 108(4) . . ?
C11 N3 H3NB 105(4) . . ?
H3NA N3 H3NB 107(5) . . ?
C14 N4 C15 113.3(3) . . ?
C14 N4 H4NA 115(3) . . ?
C15 N4 H4NA 110(3) . . ?
C14 N4 H4NB 110(3) . . ?
C15 N4 H4NB 110(3) . . ?
H4NA N4 H4NB 98(4) . . ?
C6 C5 C10 118.7(4) . . ?
C6 C5 C4 122.5(4) . . ?
C10 C5 C4 118.8(4) . . ?
C18 C19 C20 121.9(4) . . ?
C18 C19 H19A 119.1 . . ?
C20 C19 H19A 119.1 . . ?
C7 C6 C5 121.0(4) . . ?
C7 C6 H6A 119.5 . . ?
C5 C6 H6A 119.5 . . ?
C19 C18 C17 119.9(5) . . ?
C19 C18 H18A 120.0 . . ?
C17 C18 H18A 120.0 . . ?
C6 C7 C8 120.5(5) . . ?
C6 C7 H7A 119.7 . . ?
C8 C7 H7A 119.7 . . ?
C18 C17 C16 119.8(4) . . ?
C18 C17 H17A 120.1 . . ?
C16 C17 H17A 120.1 . . ?
C9 C8 C7 119.1(5) . . ?
C9 C8 H8A 120.5 . . ?
C7 C8 H8A 120.5 . . ?
C21 C16 C17 119.5(4) . . ?
C21 C16 C15 119.4(4) . . ?
C17 C16 C15 121.1(4) . . ?
C8 C9 C10 119.5(4) . . ?
C8 C9 C11 121.9(4) . . ?
C10 C9 C11 118.6(4) . . ?
C5 C10 C9 121.1(4) . . ?
C5 C10 H10A 119.5 . . ?
C9 C10 H10A 119.5 . . ?
N4 C14 C13 109.5(3) . . ?
N4 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
N4 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
C9 C11 N3 109.7(3) . . ?
C9 C11 H11A 109.7 . . ?
N3 C11 H11A 109.7 . . ?
C9 C11 H11B 109.7 . . ?
N3 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C12 C13 C14 113.0(4) . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
N3 C12 C13 111.5(4) . . ?
N3 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
N3 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N4 C15 C16 112.2(3) . . ?
N4 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
N4 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?

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
N4 H4NA Cl3 0.88(3) 2.24(3) 3.111(4) 170(4) 4_445
N4 H4NB Cl4 0.89(3) 2.14(3) 3.025(4) 178(4) .
N3 H3NA Cl4 0.88(3) 2.42(3) 3.288(4) 173(4) 4_545
N3 H3NB Cl3 0.88(3) 2.24(3) 3.095(4) 164(6) .
N1 H1N Cl4 0.90(4) 2.67(4) 3.435(4) 143(3) 4_545
N2 H2N Cl4 0.89(4) 2.51(4) 3.289(4) 147(4) 4_545

_refine_diff_density_max         1.015
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.108

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_[LH4]Cl4.2H2O
_database_code_depnum_ccdc_archive 'CCDC 985974'
_audit_update_record             
;
2015-01-23 deposited with the CCDC.
2015-01-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H36 N4, 2(H2 O), 4(Cl)'
_chemical_formula_sum            'C22 H40 Cl4 N4 O2'
_chemical_formula_weight         534.38

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9236(12)
_cell_length_b                   10.1680(17)
_cell_length_c                   10.2931(18)
_cell_angle_alpha                62.925(3)
_cell_angle_beta                 67.443(3)
_cell_angle_gamma                69.428(4)
_cell_volume                     665.97(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    4286
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      30.6

_exptl_crystal_description       'parallel pipet'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_absorpt_coefficient_mu    0.470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
SADABS;Sheldrick1996;Blessing,ActaC.1995,A51,33
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector Smart6000'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10396
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.587
_diffrn_reflns_theta_max         32.057
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3938
_reflns_number_gt                3459
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Hydrogen atoms were located from Difference Fourier Syntheses and refined. 
For the hydrogen atoms bonded to nitrogen and oxygen O-H and N-H distance 
restraints (SADI) were included in the refinement, respectively.

 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART, 1997'
_computing_cell_refinement       'Bruker SAINT, V6.45A, 2003 '
_computing_data_reduction        'Bruker SAINT, V6.45A, 2003'
_computing_structure_solution    'Bruker SHELXTL 6.14, 1998'
_computing_molecular_graphics    'Diamond 2.0'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+0.2531P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3938
_refine_ls_number_parameters     225
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.31388(5) -0.68033(4) 0.47444(4) 0.02502(9) Uani 1 1 d . . . . .
Cl2 Cl 0.25340(4) -0.07068(4) -0.11355(4) 0.02049(9) Uani 1 1 d . . . . .
O1 O 0.28323(16) -0.12852(13) 0.59809(12) 0.0267(2) Uani 1 1 d D . . . .
H2O H 0.388(3) -0.189(2) 0.591(3) 0.042(6) Uiso 1 1 d D . . . .
H1O H 0.283(4) -0.106(3) 0.667(3) 0.064(8) Uiso 1 1 d D . . . .
N1 N 0.33127(16) 0.04739(13) 0.29363(13) 0.0183(2) Uani 1 1 d D . . . .
H2N1 H 0.317(3) 0.006(2) 0.3914(16) 0.027(5) Uiso 1 1 d D . . . .
H1N1 H 0.446(2) 0.063(2) 0.253(2) 0.027(5) Uiso 1 1 d D . . . .
N2 N 0.01006(15) -0.25607(12) 0.23529(13) 0.0161(2) Uani 1 1 d D . . . .
H2N2 H -0.018(2) -0.1725(16) 0.1630(17) 0.019(4) Uiso 1 1 d D . . . .
H1N2 H -0.089(2) -0.254(2) 0.3106(19) 0.033(5) Uiso 1 1 d D . . . .
C1 C 0.33337(18) -0.06868(15) 0.24160(16) 0.0190(2) Uani 1 1 d . . . . .
H1B H 0.368(3) -0.025(2) 0.131(2) 0.024(4) Uiso 1 1 d . . . . .
H1A H 0.429(3) -0.153(2) 0.275(2) 0.028(5) Uiso 1 1 d . . . . .
C2 C 0.14590(18) -0.11336(16) 0.30061(16) 0.0206(3) Uani 1 1 d . . . . .
H2B H 0.060(3) -0.032(2) 0.245(2) 0.027(5) Uiso 1 1 d . . . . .
H2A H 0.088(3) -0.131(2) 0.403(2) 0.022(4) Uiso 1 1 d . . . . .
C3 C 0.17437(18) -0.25522(15) 0.27156(16) 0.0194(2) Uani 1 1 d . . . . .
H3A H 0.191(2) -0.341(2) 0.350(2) 0.022(4) Uiso 1 1 d . . . . .
H3B H 0.279(2) -0.259(2) 0.185(2) 0.021(4) Uiso 1 1 d . . . . .
C4 C 0.0444(2) -0.39193(15) 0.19913(17) 0.0215(3) Uani 1 1 d . . . . .
H4A H 0.044(3) -0.476(2) 0.290(2) 0.027(5) Uiso 1 1 d . . . . .
H4B H 0.167(3) -0.394(2) 0.128(2) 0.022(4) Uiso 1 1 d . . . . .
C5 C -0.10046(18) -0.37981(14) 0.13080(15) 0.0181(2) Uani 1 1 d . . . . .
C6 C -0.24368(19) -0.45892(15) 0.21451(16) 0.0214(3) Uani 1 1 d . . . . .
H6 H -0.256(3) -0.518(2) 0.322(2) 0.028(5) Uiso 1 1 d . . . . .
C7 C -0.36827(19) -0.45189(15) 0.14524(17) 0.0221(3) Uani 1 1 d . . . . .
H7 H -0.463(3) -0.509(2) 0.205(2) 0.029(5) Uiso 1 1 d . . . . .
C8 C -0.35261(18) -0.36382(15) -0.00710(16) 0.0192(2) Uani 1 1 d . . . . .
H8 H -0.439(2) -0.358(2) -0.057(2) 0.024(4) Uiso 1 1 d . . . . .
C9 C -0.21053(17) -0.28198(14) -0.09256(15) 0.0165(2) Uani 1 1 d . . . . .
C10 C -0.08489(18) -0.29208(14) -0.02247(15) 0.0177(2) Uani 1 1 d . . . . .
H10 H 0.011(3) -0.243(2) -0.079(2) 0.025(4) Uiso 1 1 d . . . . .
C11 C -0.18601(18) -0.19174(15) -0.25962(15) 0.0185(2) Uani 1 1 d . . . . .
H11B H -0.067(2) -0.1668(19) -0.3053(18) 0.017(4) Uiso 1 1 d . . . . .
H11A H -0.192(2) -0.244(2) -0.312(2) 0.022(4) 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
O1 H2O 0.843(18) . ?
O1 H1O 0.833(19) . ?
N1 C1 1.4949(17) . ?
N1 C11 1.5020(18) 2 ?
N1 H2N1 0.874(14) . ?
N1 H1N1 0.880(14) . ?
N2 C3 1.4894(16) . ?
N2 C4 1.4991(17) . ?
N2 H2N2 0.863(13) . ?
N2 H1N2 0.869(14) . ?
C1 C2 1.5207(18) . ?
C1 H1B 0.975(19) . ?
C1 H1A 0.951(19) . ?
C2 C3 1.5275(19) . ?
C2 H2B 0.973(19) . ?
C2 H2A 0.936(18) . ?
C3 H3A 0.891(19) . ?
C3 H3B 0.958(18) . ?
C4 C5 1.5057(18) . ?
C4 H4A 0.936(19) . ?
C4 H4B 0.967(18) . ?
C5 C6 1.3920(19) . ?
C5 C10 1.3953(19) . ?
C6 C7 1.390(2) . ?
C6 H6 0.973(19) . ?
C7 C8 1.388(2) . ?
C7 H7 0.950(19) . ?
C8 C9 1.4021(17) . ?
C8 H8 0.973(18) . ?
C9 C10 1.3907(17) . ?
C9 C11 1.5063(18) . ?
C10 H10 0.908(18) . ?
C11 N1 1.5020(18) 2 ?
C11 H11B 0.942(17) . ?
C11 H11A 0.937(18) . ?

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
H2O O1 H1O 99(2) . . ?
C1 N1 C11 116.84(10) . 2 ?
C1 N1 H2N1 108.0(12) . . ?
C11 N1 H2N1 108.8(13) 2 . ?
C1 N1 H1N1 104.7(12) . . ?
C11 N1 H1N1 112.1(13) 2 . ?
H2N1 N1 H1N1 105.7(17) . . ?
C3 N2 C4 111.31(10) . . ?
C3 N2 H2N2 109.8(11) . . ?
C4 N2 H2N2 112.3(12) . . ?
C3 N2 H1N2 110.2(13) . . ?
C4 N2 H1N2 109.9(14) . . ?
H2N2 N2 H1N2 103.1(17) . . ?
N1 C1 C2 113.13(11) . . ?
N1 C1 H1B 106.4(11) . . ?
C2 C1 H1B 109.9(11) . . ?
N1 C1 H1A 106.2(11) . . ?
C2 C1 H1A 111.4(11) . . ?
H1B C1 H1A 109.6(16) . . ?
C1 C2 C3 108.61(11) . . ?
C1 C2 H2B 109.1(11) . . ?
C3 C2 H2B 108.4(11) . . ?
C1 C2 H2A 114.6(11) . . ?
C3 C2 H2A 109.3(11) . . ?
H2B C2 H2A 106.6(16) . . ?
N2 C3 C2 112.02(10) . . ?
N2 C3 H3A 105.2(11) . . ?
C2 C3 H3A 113.8(11) . . ?
N2 C3 H3B 106.0(10) . . ?
C2 C3 H3B 110.2(11) . . ?
H3A C3 H3B 109.2(15) . . ?
N2 C4 C5 112.40(11) . . ?
N2 C4 H4A 106.4(12) . . ?
C5 C4 H4A 111.1(11) . . ?
N2 C4 H4B 103.9(10) . . ?
C5 C4 H4B 110.9(10) . . ?
H4A C4 H4B 111.8(15) . . ?
C6 C5 C10 119.36(12) . . ?
C6 C5 C4 121.81(12) . . ?
C10 C5 C4 118.76(12) . . ?
C7 C6 C5 120.16(13) . . ?
C7 C6 H6 120.4(11) . . ?
C5 C6 H6 119.4(11) . . ?
C8 C7 C6 120.19(12) . . ?
C8 C7 H7 121.8(12) . . ?
C6 C7 H7 118.0(12) . . ?
C7 C8 C9 120.35(12) . . ?
C7 C8 H8 121.2(11) . . ?
C9 C8 H8 118.5(11) . . ?
C10 C9 C8 118.86(12) . . ?
C10 C9 C11 120.04(11) . . ?
C8 C9 C11 121.00(11) . . ?
C9 C10 C5 121.06(12) . . ?
C9 C10 H10 119.1(11) . . ?
C5 C10 H10 119.8(11) . . ?
N1 C11 C9 113.23(11) 2 . ?
N1 C11 H11B 107.9(10) 2 . ?
C9 C11 H11B 110.4(10) . . ?
N1 C11 H11A 105.4(11) 2 . ?
C9 C11 H11A 113.6(11) . . ?
H11B C11 H11A 105.8(14) . . ?

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
O1 H2O Cl1 0.843(18) 2.276(18) 3.1077(12) 169(2) 2_646
O1 H1O Cl2 0.833(19) 2.36(2) 3.1882(13) 171(3) 1_556
N1 H1N1 Cl2 0.880(14) 2.270(14) 3.1290(12) 165.2(17) 2_655
N2 H2N2 Cl2 0.863(13) 2.488(15) 3.2108(12) 141.8(15) 2
N1 H2N1 O1 0.874(14) 1.907(14) 2.7615(16) 165.4(18) .
N2 H2N2 Cl2 0.863(13) 2.826(16) 3.3533(12) 121.0(13) .
N2 H1N2 Cl1 0.869(14) 2.231(15) 3.0753(12) 163.8(19) 2_546

_refine_diff_density_max         0.541
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.069

_shelxl_version_number           2014/6

