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_7714210
_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 Cl4 Co N4 O3 Zn2'
_chemical_formula_sum            'C8 H22 Cl4 Co N4 O3 Zn2'
_chemical_formula_weight         553.76
_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_Hall           'A 2 -2ab'
_space_group_name_H-M_alt        'A e a 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-03-28
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.8579(7)
_cell_length_b                   11.1659(3)
_cell_length_c                   13.2095(3)
_cell_measurement_reflns_used    19487
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      77.0912
_cell_measurement_theta_min      3.4156
_cell_volume                     3813.94(17)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector_area_resol_mean 10.6501
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -92.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  125.0000 -180.0000 90

  2 omega -110.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -77.0000   90.0000 102

  3 omega   17.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6255   57.0000   30.0000 94

  4 omega  -26.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6255  -57.0000  -90.0000 94

  5 omega  -29.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6255  -37.0000  120.0000 92

  6 omega   41.00  122.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  -30.0000 81

  7 omega   89.00  178.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000    0.0000 89

  8 omega   41.00   98.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  150.0000 57

  9 omega   41.00   98.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  -30.0000 57

 10 omega   40.00  141.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000  150.0000 101

 11 omega   43.00  137.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -61.0000 -120.0000 94

 12 omega   40.00  141.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000    0.0000 101

 13 omega   41.00   98.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000   30.0000 57

 14 omega   31.00  109.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  -30.0000 78

 15 omega   89.00  178.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000  120.0000 89

 16 omega   38.00   91.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000   90.0000 53

 17 omega   38.00   91.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000 -180.0000 53

 18 omega   41.00  122.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000 -120.0000 81

 19 omega   41.00  122.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  120.0000 81

 20 omega   90.00  178.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000   60.0000 88

 21 omega   89.00  178.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000   90.0000 89

 22 omega   31.00  109.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  150.0000 78

 23 omega   41.00  122.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000   60.0000 81

 24 omega   41.00   98.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000 -180.0000 57

 25 omega   89.00  178.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000   60.0000 89

 26 omega   82.00  178.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   71.0000  140.3963 96

 27 omega   12.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6255   77.0000   90.0000 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   17.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6255   57.0000  -90.0000 94

 30 omega   12.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6255   77.0000 -150.0000 102

 31 omega    1.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6255  -99.0000   60.0000 80

 32 omega   22.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6255   37.0000 -150.0000 92

 33 omega   71.00  178.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000  -90.0000 107

 34 omega   81.00  120.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000    0.0000 39

 35 omega   83.00  178.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   67.0000  -49.7163 95

 36 omega   85.00  178.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000  -90.0000 93

 37 omega   85.00  178.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000 -180.0000 93

 38 omega   85.00  178.00   1.0000    1.5350
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000  -60.0000 93
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0256284000
_diffrn_orient_matrix_UB_12      -0.0183206000
_diffrn_orient_matrix_UB_13      -0.0575803000
_diffrn_orient_matrix_UB_21      -0.0961713000
_diffrn_orient_matrix_UB_22      -0.0764853000
_diffrn_orient_matrix_UB_23      -0.0066111000
_diffrn_orient_matrix_UB_31      -0.0607685000
_diffrn_orient_matrix_UB_32      0.1133292000
_diffrn_orient_matrix_UB_33      -0.0138637000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35287
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.465
_diffrn_reflns_theta_min         3.418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    14.951
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13120
_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    1.929
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2216
_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.760
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.110
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.049(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3509
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0510P)^2^+22.5586P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0886
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3482
_reflns_number_total             3509
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt01634j2.cif
_cod_data_source_block           exp_84
_cod_original_sg_symbol_Hall     'A 2 -2ac'
_cod_database_code               7714210
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.396
_shelx_estimated_absorpt_t_min   0.104
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.951(7)
 0.049(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H,H) groups, All N(H,H) groups
3. Restrained distances
 N4-H4A
 0.98 with sigma of 0.02
 H4B-N4
 0.98 with sigma of 0.02
 N1-H1
 0.98 with sigma of 0.02
 N3-H3
 0.98 with sigma of 0.02
4.a Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C1(H1A,H1B), C2(H2C,H2D), C7(H7A,H7B), C8(H8A,H8B), C5(H5A,H5B),
 C6(H6A,H6B), C4(H4C,H4D), C3(H3A,H3B)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              27634
_shelx_fab_checksum              60513
_olex2_submission_special_instructions 'No special instructions were received'