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_7714208
_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 Cl5 Co N4 O2 Zn2'
_chemical_formula_sum            'C8 H22 Cl5 Co N4 O2 Zn2'
_chemical_formula_weight         573.21
_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   geom
_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                76.033(5)
_cell_angle_beta                 79.660(5)
_cell_angle_gamma                74.106(6)
_cell_formula_units_Z            2
_cell_length_a                   8.0188(6)
_cell_length_b                   9.4646(6)
_cell_length_c                   13.1434(8)
_cell_measurement_reflns_used    9138
_cell_measurement_temperature    202(110)
_cell_measurement_theta_max      76.5954
_cell_measurement_theta_min      3.4882
_cell_volume                     924.12(11)
_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      202(110)
_diffrn_detector_area_resol_mean 10.6501
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega -116.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -19.0000  150.0000 111

  2 omega  -49.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000  -30.0000 82

  3 omega  -92.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  125.0000   30.0000 90

  4 omega   23.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6255 -125.0000   30.0000 73

  5 omega   12.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6255   77.0000 -180.0000 102

  6 omega   71.00  178.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000  150.0000 107

  7 omega   38.00   91.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000    0.0000 53

  8 omega   41.00  122.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000    0.0000 81

  9 omega   94.00  178.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000  120.0000 84

 10 omega   41.00  122.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  150.0000 81

 11 omega   41.00  122.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  -90.0000 81

 12 omega   89.00  178.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000 -180.0000 89

 13 omega   31.00  109.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000   30.0000 78

 14 omega   41.00   98.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  120.0000 57

 15 omega   31.00  109.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  150.0000 78

 16 omega   31.00  109.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000   60.0000 78

 17 omega   31.00  109.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  -90.0000 78

 18 omega   43.00  137.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -61.0000 -120.0000 94

 19 omega   90.00  178.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000 -120.0000 88

 20 omega   38.00   91.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000 -150.0000 53

 21 omega   38.00   91.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000   60.0000 53

 22 omega   85.00  178.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000   30.0000 93

 23 omega   12.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6255   77.0000   90.0000 102

 24 omega   17.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6255   57.0000   90.0000 94

 25 omega   17.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6255   57.0000    0.0000 94

 26 omega   17.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6255   57.0000  -60.0000 94

 27 omega   12.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6255   77.0000 -120.0000 102

 28 omega   12.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6255   77.0000  -60.0000 102

 29 omega    1.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6255  -99.0000 -150.0000 80

 30 omega   85.00  178.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000 -120.0000 93

 31 omega   85.00  178.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000  -30.0000 93

 32 omega   81.00  178.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000  120.0000 97

 33 omega   85.00  178.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000   60.0000 93

 34 omega   85.00  178.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000    0.0000 93

 35 omega   85.00  178.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000  -90.0000 93

 36 omega   81.00  178.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000 -180.0000 97

 37 omega   90.00  178.00   1.0000    3.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000  -30.0000 88
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0212294000
_diffrn_orient_matrix_UB_12      -0.1412496000
_diffrn_orient_matrix_UB_13      0.0836716000
_diffrn_orient_matrix_UB_21      0.1689333000
_diffrn_orient_matrix_UB_22      -0.0042628000
_diffrn_orient_matrix_UB_23      0.0422027000
_diffrn_orient_matrix_UB_31      -0.1072916000
_diffrn_orient_matrix_UB_32      0.0995289000
_diffrn_orient_matrix_UB_33      0.0776216000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16321
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.493
_diffrn_reflns_theta_min         3.491
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    16.711
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35375
_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            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    2.060
_exptl_crystal_description       plate
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.1529
_exptl_crystal_size_mid          0.1025
_exptl_crystal_size_min          0.0697
_refine_diff_density_max         2.001
_refine_diff_density_min         -0.977
_refine_diff_density_rms         0.278
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3394
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.211
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0765
_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/[\s^2^(Fo^2^)+(0.0562P)^2^+43.1033P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2485
_refine_ls_wR_factor_ref         0.2492
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3228
_reflns_number_total             3394
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt01634j2.cif
_cod_data_source_block           exp76a
_cod_database_code               7714208
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 S O2'
_reflns_odcompleteness_completeness 99.97
_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, All N(H) groups, All N(H,H) groups
2. Restrained distances
 H1B-N1
 0.86 with sigma of 0.02
 H1A-N1
 0.86 with sigma of 0.02
 H2-N2
 0.86 with sigma of 0.02
 H3-N3
 0.86 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 N3(H3), N2(H2)
3.b Secondary CH2 refined with riding coordinates:
 N4(H4A,H4B), N1(H1A,H1B), C8(H8A,H8B), C7(H7A,H7B), C2(H2A,H2B), C1(H1C,H1D),
 C5(H5A,H5B), C6(H6A,H6B), C4(H4C,H4D), C3(H3A,H3B)
;
_shelx_res_checksum              7214
_olex2_submission_special_instructions 'No special instructions were received'