Synthesis of Nitrogen Mustards on Cobalt(III)
Kariyawasam, Rasika Janadari; Zibaseresht, Ramin; Polson, Matthew Ian James; Houlihan, Joanna C.C.; Wikaira, Jan L.; Hartshorn, Richard M.; Dalton Transactions  (2023) –; doi:10.1039/D3DT01634J

data_7714212
_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 H22 Cl2 Co N6 O4, Cl'
_chemical_formula_sum            'C8 H22 Cl3 Co N6 O4'
_chemical_formula_weight         431.59
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-03-17
_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                77.760(7)
_cell_angle_beta                 78.576(7)
_cell_angle_gamma                83.603(7)
_cell_formula_units_Z            6
_cell_length_a                   13.5798(13)
_cell_length_b                   14.7189(12)
_cell_length_c                   15.3910(13)
_cell_measurement_reflns_used    7204
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.7893
_cell_measurement_theta_min      3.3263
_cell_volume                     2939.1(5)
_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 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
  1 omega  -50.00   33.00   1.0000    4.5400
omega____ theta____ kappa____ phi______ frames
    -      -41.0853   38.0000 -180.0000 83

  2 omega  -50.00   33.00   1.0000    4.5400
omega____ theta____ kappa____ phi______ frames
    -      -41.0853   38.0000   60.0000 83

  3 omega  -50.00   33.00   1.0000    4.5400
omega____ theta____ kappa____ phi______ frames
    -      -41.0853   38.0000 -150.0000 83

  4 omega  -50.00   33.00   1.0000    4.5400
omega____ theta____ kappa____ phi______ frames
    -      -41.0853   38.0000   90.0000 83

  5 omega -113.00  -13.00   1.0000    4.5400
omega____ theta____ kappa____ phi______ frames
    -      -41.0853  -57.0000  -90.0000 100

  6 omega    1.00   82.00   1.0000    4.5400
omega____ theta____ kappa____ phi______ frames
    -       41.0853  -99.0000   60.0000 81

  7 omega   23.00   97.00   1.0000    4.5400
omega____ theta____ kappa____ phi______ frames
    -       41.0853 -125.0000 -120.0000 74

  8 omega   36.00  116.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -150.0000 80

  9 omega   36.00  116.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -30.0000 80

 10 omega   36.00  145.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000    0.0000 109

 11 omega   36.00  116.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -120.0000 80

 12 omega   36.00  116.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   60.0000 80

 13 omega   39.00   98.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   60.0000 59

 14 omega   59.00  178.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000   60.0000 119

 15 omega   36.00   91.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 55

 16 omega   57.00  151.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000 -120.0000 94

 17 omega   36.00   91.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -90.0000 55

 18 omega   39.00   98.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  120.0000 59

 19 omega   86.00  178.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   60.0000 92

 20 omega   39.00   98.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 59

 21 omega   36.00  116.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   30.0000 80

 22 omega   57.00  151.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  -90.0000 94

 23 omega   36.00  116.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000    0.0000 80

 24 omega   40.00  141.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -150.0000 101

 25 omega   36.00   91.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 55

 26 omega   36.00  116.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  150.0000 80

 27 omega  100.00  178.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -150.0000 78

 28 omega   96.00  178.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   90.0000 82

 29 omega   59.00  177.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000 -150.0000 118

 30 omega   46.00   72.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   60.0000 26

 31 omega   46.00  137.00   1.0000   18.1600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -180.0000 91
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0065006000
_diffrn_orient_matrix_UB_12      0.1010690000
_diffrn_orient_matrix_UB_13      -0.0531489000
_diffrn_orient_matrix_UB_21      -0.0621995000
_diffrn_orient_matrix_UB_22      0.0316947000
_diffrn_orient_matrix_UB_23      0.0849358000
_diffrn_orient_matrix_UB_31      0.0977499000
_diffrn_orient_matrix_UB_32      0.0176506000
_diffrn_orient_matrix_UB_33      0.0283084000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            42568
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.993
_diffrn_reflns_theta_min         3.329
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.842
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37529
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       block
_exptl_crystal_F_000             1332
_exptl_crystal_size_max          0.4345
_exptl_crystal_size_mid          0.2133
_exptl_crystal_size_min          0.1539
_refine_diff_density_max         1.917
_refine_diff_density_min         -1.399
_refine_diff_density_rms         0.184
_refine_ls_extinction_coef       0.00055(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     671
_refine_ls_number_reflns         12250
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      0.904
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0803
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1879P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2503
_refine_ls_wR_factor_ref         0.3191
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3900
_reflns_number_total             12250
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt01634j2.cif
_cod_data_source_block           exp98a
_cod_database_code               7714212
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 S O2'
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All N(H) groups, All N(H,H) groups, All Cl(H,H,H) groups
2. Restrained distances
 H3-N3
 0.86 with sigma of 0.02
 N6-H6C
 0.86 with sigma of 0.02
 N16-H16A
 0.86 with sigma of 0.02
 H17-N17
 0.86 with sigma of 0.02
 N9-H9
 0.86 with sigma of 0.02
 H6D-N6
 0.86 with sigma of 0.02
 H5-N5
 0.86 with sigma of 0.02
 H15-N15
 0.86 with sigma of 0.02
 H16B-N16
 0.86 with sigma of 0.02
 H10C-N10
 0.86 with sigma of 0.02
 H12C-N12
 0.86 with sigma of 0.02
 H12D-N12
 0.86 with sigma of 0.02
 H6C-H6D
 1.3 with sigma of 0.02
 H12D-H12C
 1.3 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N7) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Others
 Fixed Sof: Cl7(0.5) Cl12(0.5) Cl11(0.5) Cl9(0.5) Cl8(0.5) Cl10(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C19(H19A,H19B), C20(H20A,H20B), C22(H22A,
 H22B), C21(H21A,H21B), C18(H18A,H18B), C17(H17A,H17B), C3(H3A,H3B), C4(H4A,
 H4B), C7(H7A,H7B), C8(H8A,H8B), C2(H2A,H2B), C1(H1A,H1B), C6(H6A,H6B), C5(H5A,
 H5B), N4(H4C,H4D), C15(H15A,H15B), C16(H16C,H16D), C11(H11A,H11B), C12(H12A,
 H12B), C14(H14A,H14B), C13(H13A,H13B), C10(H10A,H10B), C9(H9A,H9B)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              84019
_shelx_fab_checksum              7040
_olex2_submission_special_instructions 'No special instructions were received'