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#$Date: 2023-10-13 02:09:49 +0300 (Fri, 13 Oct 2023) $
#$Revision: 286946 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/42/7714213.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_7714213
loop_
_publ_author_name
'Kariyawasam, Rasika Janadari'
'Zibaseresht, Ramin'
'Polson, Matthew Ian James'
'Houlihan, Joanna C.C.'
'Wikaira, Jan L.'
'Hartshorn, Richard M.'
_publ_section_title
;
 Synthesis of Nitrogen Mustards on Cobalt(III)
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT01634J
_journal_year                    2023
_chemical_formula_moiety         'C8 H24 Cl2 Co N4 O2, Cl'
_chemical_formula_sum            'C8 H24 Cl3 Co N4 O2'
_chemical_formula_weight         373.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-03-31 deposited with the CCDC.	2023-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.647(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5210(7)
_cell_length_b                   10.6094(6)
_cell_length_c                   12.7807(8)
_cell_measurement_reflns_used    3968
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.3475
_cell_measurement_theta_min      3.4950
_cell_volume                     1544.44(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector_area_resol_mean 10.6501
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11198
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.475
_diffrn_reflns_theta_min         4.821
_exptl_absorpt_coefficient_mu    13.508
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.1147
_exptl_crystal_size_mid          0.0697
_exptl_crystal_size_min          0.0572
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2814
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0426
_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)+(0.0499P)²+1.8498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1081
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2264
_reflns_number_total             2814
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt01634j2.cif
_cod_data_source_block           kjk35ab
_cod_database_code               7714213
_shelx_shelxl_version_number     2018/3
_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.
;
_exptl_absorpt_special_details
;
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H,H,H) groups
2. Restrained distances
 H1B-N1
 0.86 with sigma of 0.02
 H1A-N1
 0.86 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C1(H1C,H1D), C2(H2B,H2C), C5(H5A,H5B), C6(H6A,H6B), C4(H4C,H4D), C3(H3A,H3B),
 C7(H7A,H7B), C8(H8A,H8B)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
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 0.56632(5) 0.32855(6) 0.30763(5) 0.01883(17) Uani 1 1 d . . . . .
Cl1 Cl 0.55186(8) 0.12901(9) 0.24795(8) 0.0281(2) Uani 1 1 d . . . . .
Cl2 Cl 0.57522(8) 0.52980(8) 0.36448(7) 0.0226(2) Uani 1 1 d . . . . .
Cl3 Cl 0.35327(9) 0.59211(10) 0.12373(8) 0.0301(2) Uani 1 1 d . . . . .
O1 O 0.9351(3) 0.2078(3) 0.4631(3) 0.0346(7) Uani 1 1 d . . . . .
O2 O 0.6925(3) 0.2958(3) 0.6575(2) 0.0298(7) Uani 1 1 d . . . . .
N2 N 0.7418(3) 0.3113(3) 0.3287(3) 0.0232(7) Uani 1 1 d . . . . .
N1 N 0.5798(3) 0.3923(3) 0.1665(3) 0.0259(7) Uani 1 1 d D . . . .
N4 N 0.3966(3) 0.3456(3) 0.2780(3) 0.0224(7) Uani 1 1 d . . . . .
N3 N 0.5427(3) 0.2718(3) 0.4526(3) 0.0209(7) Uani 1 1 d . . . . .
C1 C 0.7025(4) 0.4291(4) 0.1635(3) 0.0279(9) Uani 1 1 d . . . . .
H1C H 0.718934 0.510356 0.197249 0.033 Uiso 1 1 calc R U . . .
H1D H 0.717233 0.434822 0.090908 0.033 Uiso 1 1 calc R U . . .
C2 C 0.7785(4) 0.3288(4) 0.2220(3) 0.0276(9) Uani 1 1 d . . . . .
H2B H 0.769562 0.250258 0.182777 0.033 Uiso 1 1 calc R U . . .
H2C H 0.860318 0.353834 0.229939 0.033 Uiso 1 1 calc R U . . .
C5 C 0.8137(3) 0.3869(4) 0.4132(3) 0.0254(8) Uani 1 1 d . . . . .
H5A H 0.777085 0.384483 0.476774 0.031 Uiso 1 1 calc R U . . .
H5B H 0.815261 0.474058 0.390457 0.031 Uiso 1 1 calc R U . . .
C6 C 0.9386(4) 0.3384(4) 0.4388(4) 0.0302(9) Uani 1 1 d . . . . .
H6A H 0.979493 0.351001 0.378602 0.036 Uiso 1 1 calc R U . . .
H6B H 0.980232 0.384081 0.498655 0.036 Uiso 1 1 calc R U . . .
C4 C 0.3480(3) 0.3443(4) 0.3793(3) 0.0233(8) Uani 1 1 d . . . . .
H4C H 0.264814 0.324803 0.366755 0.028 Uiso 1 1 calc R U . . .
H4D H 0.358692 0.425788 0.413862 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4145(3) 0.2443(4) 0.4466(3) 0.0232(8) Uani 1 1 d . . . . .
H3A H 0.392501 0.244866 0.516914 0.028 Uiso 1 1 calc R U . . .
H3B H 0.396625 0.161833 0.415483 0.028 Uiso 1 1 calc R U . . .
C7 C 0.6160(4) 0.1703(4) 0.5099(3) 0.0260(9) Uani 1 1 d . . . . .
H7A H 0.693961 0.172820 0.490113 0.031 Uiso 1 1 calc R U . . .
H7B H 0.581613 0.088961 0.489064 0.031 Uiso 1 1 calc R U . . .
C8 C 0.6252(4) 0.1848(4) 0.6286(3) 0.0292(9) Uani 1 1 d . . . . .
H8A H 0.547667 0.192736 0.648807 0.035 Uiso 1 1 calc R U . . .
H8B H 0.663566 0.111815 0.664143 0.035 Uiso 1 1 calc R U . . .
H2A H 0.754(5) 0.237(5) 0.346(4) 0.044 Uiso 1 1 d . U . . .
H1 H 0.994(5) 0.173(5) 0.439(4) 0.044 Uiso 1 1 d . U . . .
H2 H 0.677(5) 0.328(5) 0.712(4) 0.044 Uiso 1 1 d . U . . .
H3 H 0.562(5) 0.340(5) 0.484(4) 0.044 Uiso 1 1 d . U . . .
H4A H 0.378(5) 0.408(5) 0.242(4) 0.044 Uiso 1 1 d . U . . .
H4B H 0.363(5) 0.284(5) 0.238(4) 0.044 Uiso 1 1 d . U . . .
H1A H 0.530(4) 0.453(3) 0.156(4) 0.044 Uiso 1 1 d D U . . .
H1B H 0.558(5) 0.333(4) 0.122(3) 0.044 Uiso 1 1 d D U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Co1 Cl2 178.20(4) . . ?
N2 Co1 Cl1 88.93(10) . . ?
N2 Co1 Cl2 92.70(10) . . ?
N1 Co1 Cl1 91.41(11) . . ?
N1 Co1 Cl2 87.92(11) . . ?
N1 Co1 N2 86.38(14) . . ?
N1 Co1 N3 175.84(14) . . ?
N4 Co1 Cl1 90.01(11) . . ?
N4 Co1 Cl2 88.31(11) . . ?
N4 Co1 N2 176.49(14) . . ?
N4 Co1 N1 90.30(15) . . ?
N4 Co1 N3 86.32(14) . . ?
N3 Co1 Cl1 91.00(10) . . ?
N3 Co1 Cl2 89.57(10) . . ?
N3 Co1 N2 97.05(13) . . ?
C6 O1 H1 107(3) . . ?
C8 O2 H2 112(4) . . ?
Co1 N2 H2A 104(4) . . ?
C2 N2 Co1 106.4(2) . . ?
C2 N2 H2A 108(4) . . ?
C5 N2 Co1 119.1(3) . . ?
C5 N2 C2 113.0(3) . . ?
C5 N2 H2A 106(4) . . ?
Co1 N1 H1A 105(3) . . ?
Co1 N1 H1B 107(3) . . ?
C1 N1 Co1 109.0(2) . . ?
C1 N1 H1A 114(4) . . ?
C1 N1 H1B 111(4) . . ?
H1A N1 H1B 109(5) . . ?
Co1 N4 H4A 111(4) . . ?
Co1 N4 H4B 113(3) . . ?
C4 N4 Co1 109.2(2) . . ?
C4 N4 H4A 113(4) . . ?
C4 N4 H4B 108(3) . . ?
H4A N4 H4B 102(5) . . ?
Co1 N3 H3 97(4) . . ?
C3 N3 Co1 106.3(2) . . ?
C3 N3 H3 113(4) . . ?
C7 N3 Co1 121.7(3) . . ?
C7 N3 C3 111.5(3) . . ?
C7 N3 H3 107(4) . . ?
N1 C1 H1C 110.4 . . ?
N1 C1 H1D 110.4 . . ?
N1 C1 C2 106.8(3) . . ?
H1C C1 H1D 108.6 . . ?
C2 C1 H1C 110.4 . . ?
C2 C1 H1D 110.4 . . ?
N2 C2 C1 108.5(3) . . ?
N2 C2 H2B 110.0 . . ?
N2 C2 H2C 110.0 . . ?
C1 C2 H2B 110.0 . . ?
C1 C2 H2C 110.0 . . ?
H2B C2 H2C 108.4 . . ?
N2 C5 H5A 109.2 . . ?
N2 C5 H5B 109.2 . . ?
N2 C5 C6 112.2(3) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
O1 C6 C5 108.8(3) . . ?
O1 C6 H6A 109.9 . . ?
O1 C6 H6B 109.9 . . ?
C5 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
N4 C4 H4C 110.5 . . ?
N4 C4 H4D 110.5 . . ?
N4 C4 C3 106.2(3) . . ?
H4C C4 H4D 108.7 . . ?
C3 C4 H4C 110.5 . . ?
C3 C4 H4D 110.5 . . ?
N3 C3 C4 107.9(3) . . ?
N3 C3 H3A 110.1 . . ?
N3 C3 H3B 110.1 . . ?
C4 C3 H3A 110.1 . . ?
C4 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
N3 C7 H7A 109.3 . . ?
N3 C7 H7B 109.3 . . ?
N3 C7 C8 111.6(3) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
O2 C8 C7 107.3(3) . . ?
O2 C8 H8A 110.3 . . ?
O2 C8 H8B 110.3 . . ?
C7 C8 H8A 110.3 . . ?
C7 C8 H8B 110.3 . . ?
H8A C8 H8B 108.5 . . ?
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 Cl1 2.2479(11) . ?
Co1 Cl2 2.2528(11) . ?
Co1 N2 2.008(3) . ?
Co1 N1 1.954(4) . ?
Co1 N4 1.943(3) . ?
Co1 N3 2.006(3) . ?
O1 C6 1.422(5) . ?
O1 H1 0.87(5) . ?
O2 C8 1.428(5) . ?
O2 H2 0.81(5) . ?
N2 C2 1.498(5) . ?
N2 C5 1.493(5) . ?
N2 H2A 0.83(5) . ?
N1 C1 1.473(5) . ?
N1 H1A 0.860(19) . ?
N1 H1B 0.859(19) . ?
N4 C4 1.486(5) . ?
N4 H4A 0.82(5) . ?
N4 H4B 0.88(5) . ?
N3 C3 1.496(5) . ?
N3 C7 1.490(5) . ?
N3 H3 0.84(5) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C1 C2 1.504(6) . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.517(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C4 H4C 0.9700 . ?
C4 H4D 0.9700 . ?
C4 C3 1.502(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.513(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
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
Co1 N2 C2 C1 37.6(4) . . . . ?
Co1 N2 C5 C6 164.5(3) . . . . ?
Co1 N1 C1 C2 41.6(4) . . . . ?
Co1 N4 C4 C3 -41.4(3) . . . . ?
Co1 N3 C3 C4 -40.1(3) . . . . ?
Co1 N3 C7 C8 152.8(3) . . . . ?
N2 C5 C6 O1 -53.8(5) . . . . ?
N1 C1 C2 N2 -52.6(4) . . . . ?
N4 C4 C3 N3 53.8(4) . . . . ?
N3 C7 C8 O2 -68.0(4) . . . . ?
C2 N2 C5 C6 -69.5(4) . . . . ?
C5 N2 C2 C1 -94.8(4) . . . . ?
C3 N3 C7 C8 -80.5(4) . . . . ?
C7 N3 C3 C4 -174.8(3) . . . . ?
