A sugar-derived ligand for room temperature aerial oxidation or non-aqueous Markovnikov hydration of styrenes using a preformed or in situ generated Co complex
Pandey, Sachchida Nand; Sengupta, Arunava; Bera, Rajib; Ali, Sohel; Yadav, Somnath; Catalysis Science & Technology 14 (2024) 4487–4495; doi:10.1039/D4CY00522H

data_1571885
_publ_section_title
;
 A sugar-derived ligand for room temperature aerial oxidation or
 non-aqueous Markovnikov hydration of styrenes using a preformed or in
 situ generated Co complex
;
_journal_issue                   16
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              4487
_journal_page_last               4495
_journal_paper_doi               10.1039/D4CY00522H
_journal_volume                  14
_journal_year                    2024
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C49 H62 Co N2 O5'
_chemical_formula_sum            'C49 H62 Co N2 O5'
_chemical_formula_weight         817.93
_chemical_name_common            Co(II)-RibN2
_chemical_name_systematic        8
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-04-07
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-04-07 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                101.429(3)
_cell_angle_beta                 106.498(4)
_cell_angle_gamma                92.924(4)
_cell_formula_units_Z            2
_cell_length_a                   11.4614(6)
_cell_length_b                   12.9693(5)
_cell_length_c                   15.9143(6)
_cell_measurement_reflns_used    7465
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5980
_cell_measurement_theta_min      2.3330
_cell_volume                     2208.70(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0303
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -8.00  37.00   1.00   65.00    --   14.69  77.00   0.00   45
  2  \w     27.00  54.00   1.00   65.00    --   14.69 -99.00-120.00   27
  3  \w      8.00  34.00   1.00   65.00    --   14.69  77.00  90.00   26
  4  \w    -29.00  34.00   1.00   65.00    --   14.69 -77.00  30.00   63
  5  \w    -50.00  25.00   1.00   65.00    --   14.69 -57.00 150.00   75
  6  \w     -2.00  80.00   1.00   65.00    --   14.69  57.00 -90.00   82
  7  \w    -29.00  50.00   1.00   65.00    --  -16.64  57.00 120.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0636056000
_diffrn_orient_matrix_UB_12      -0.0015778000
_diffrn_orient_matrix_UB_13      0.0061904000
_diffrn_orient_matrix_UB_21      0.0079932000
_diffrn_orient_matrix_UB_22      0.0557326000
_diffrn_orient_matrix_UB_23      0.0051363000
_diffrn_orient_matrix_UB_31      0.0105500000
_diffrn_orient_matrix_UB_32      0.0067696000
_diffrn_orient_matrix_UB_33      0.0469906000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17333
_diffrn_reflns_point_group_measured_fraction_full 0.715
_diffrn_reflns_point_group_measured_fraction_max 0.715
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         1.869
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       block
_exptl_crystal_F_000             873
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 2541 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1051
_refine_ls_number_reflns         11148
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0462P)^2^+0.1346P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0953
_reflns_Friedel_coverage         0.431
_reflns_Friedel_fraction_full    0.430
_reflns_Friedel_fraction_max     0.430
_reflns_number_gt                9626
_reflns_number_total             11148
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cy00522h2.cif
_cod_data_source_block           8
_cod_depositor_comments
;
          Adding full bibliography for 1571885.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C98 H123 Co2 N4 O10'
_cod_original_formula_weight         1634.86
_cod_original_formula_moiety         'C49 H62 Co N2 O5, C49 H61 Co N2 O5'
_cod_original_formula_units_Z            1
_cod_original_cell_volume        2208.70(17)
_cod_database_code               1571885
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C49 H62 N2 Co O5'
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.925
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C99) \\sim Ueq, Uanis(C100) \\sim Ueq, Uanis(C97) \\sim Ueq, Uanis(C96)
\\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C97) \\sim Ueq, Uanis(C99) \\sim Ueq, Uanis(C96) \\sim Ueq: with sigma of
0.0001 and sigma for terminal atoms of 0.0002
3.a Ternary CH refined with riding coordinates:
 C18(H18), C69(H69), C20(H20), C16(H16), C67(H67), C65(H65), C19(H19), C68(H68)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C43(H43A,H43B), C93(H93A,H93B), C36(H36A,H36B), C86(H86A,H86B)
3.c Aromatic/amide H refined with riding coordinates:
 C56(H56), C72(H72), C15(H15), C7(H7), C45(H45), C62(H62), C64(H64), C79(H79),
 C23(H23), C70(H70), C39(H39), C21(H21), C91(H91), C38(H38), C49(H49), C41(H41),
  C13(H13), C40(H40), C66(H66), C46(H46), C90(H90), C92(H92), C29(H29),
 C89(H89), C47(H47), C100(H100), C88(H88), C48(H48), C42(H42), C97(H97),
 C96(H96), C95(H95), C99(H99)
3.d Idealised Me refined as rotating group:
 C55(H55A,H55B,H55C), C59(H59A,H59B,H59C), C83(H83A,H83B,H83C), C60(H60A,H60B,
 H60C), C4(H4A,H4B,H4C), C10(H10A,H10B,H10C), C32(H32A,H32B,H32C), C33(H33A,
 H33B,H33C), C76(H76A,H76B,H76C), C84(H84A,H84B,H84C), C61(H61A,H61B,H61C),
 C77(H77A,H77B,H77C), C54(H54A,H54B,H54C), C82(H82A,H82B,H82C), C26(H26A,H26B,
 H26C), C5(H5A,H5B,H5C), C11(H11A,H11B,H11C), C53(H53A,H53B,H53C), C74(H74A,
 H74B,H74C), C12(H12A,H12B,H12C), C6(H6A,H6B,H6C), C27(H27A,H27B,H27C),
 C34(H34A,H34B,H34C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              99662
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.660
_oxdiff_exptl_absorpt_empirical_full_min 0.721