#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:52:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180100 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/46/7054643.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7054643
loop_
_publ_author_name
'Khandar, Ali Akbar'
'Kirschbaum, Kristin'
'Abedi, Marjan'
'Mock, Kristi'
'Tracy, Greg'
'Spasojevic, Vojislav'
'Hosseini-Yazdi, Seyed Abolfazl'
_publ_section_title
;
 Synthesis, characterization and crystal structures of mono and dinuclear
 macrocyclic cobalt(ii) complexes with a new tetraaza m-xylyl-based
 macrocyclic ligand
;
_journal_issue                   4
_journal_name_full               'New J. Chem.'
_journal_page_first              2822
_journal_paper_doi               10.1039/C4NJ01608D
_journal_volume                  39
_journal_year                    2015
_chemical_absolute_configuration R,S
_chemical_formula_moiety         '[C22 H34 Cl2 Co N4][Cl]2'
_chemical_formula_sum            'C22 H34 Cl4 Co N4'
_chemical_formula_weight         555.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-01-23 deposited with the CCDC.
2015-01-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8736(2)
_cell_length_b                   13.6929(3)
_cell_length_c                   21.0647(6)
_cell_measurement_reflns_used    3978
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.4
_cell_volume                     2559.47(11)
_computing_cell_refinement       'Bruker SAINT, V6.45A, 2003 '
_computing_data_collection       'Bruker SMART, 1997'
_computing_data_reduction        'Bruker SAINT, V6.45A, 2003'
_computing_molecular_graphics    'Diamond 2.0'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL 6.14, 1998'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'CCD detector Smart6000'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            20953
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         33.449
_diffrn_reflns_theta_min         1.774
_exptl_absorpt_coefficient_mu    1.106
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS;Sheldrick1996;Blessing,ActaC.1995,A51,33
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       orthorhombic
_exptl_crystal_F_000             1156
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.015
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.108
_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)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         9030
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0687P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1336
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.866
_reflns_number_gt                6803
_reflns_number_total             9030
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4nj01608d1.cif
_cod_data_source_block           added_by_encifer
_cod_depositor_comments
'Adding full bibliography for 7054642--7054644.cif.'
_cod_database_code               7054643
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelxl_version_number           2014/6
#END Tags that were not found in dictionaries
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'
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
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 .
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'
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_3
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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_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
