Synthesis of Central Chirality-Containing Triarylmethanols and Triarylmethyl Radicals with Extraordinarily Stable Configurations.
Li, Yingchun; Zhai, Weixiang; Liao, Yongfang; Nie, Jiangping; Han, Guifang; Song, Yuguang; Li, Shaoyong; Hou, Jingli; Liu, Yangping; The Journal of organic chemistry 84 (2019) 11774–11782; doi:10.1021/acs.joc.9b01675

data_4034493
_publ_section_title
;
 Synthesis of Central Chirality-Containing Triarylmethanols and
 Triarylmethyl Radicals with Extraordinarily Stable Configurations.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11774
_journal_page_last               11782
_journal_paper_doi               10.1021/acs.joc.9b01675
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C37 H38 O3 S12, 1.5(C H2 Cl2)'
_chemical_formula_sum            'C38.5 H41 Cl3 O3 S12'
_chemical_formula_weight         1042.78
_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
_audit_creation_date             2018-07-26
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_cell_angle_alpha                91.8589(3)
_cell_angle_beta                 110.3299(4)
_cell_angle_gamma                98.7848(4)
_cell_formula_units_Z            4
_cell_length_a                   14.03840(8)
_cell_length_b                   18.16861(8)
_cell_length_c                   19.83360(7)
_cell_measurement_reflns_used    115777
_cell_measurement_temperature    120.01(11)
_cell_measurement_theta_max      74.2490
_cell_measurement_theta_min      3.2630
_cell_volume                     4667.96(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(11)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.976
_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    -73.00  45.00   0.50    0.50    --   16.00 -50.00 164.86  236
  2  \w     -9.00 117.00   0.50    0.50    --   28.00  82.00 156.64  252
  3  \w     11.00 137.00   0.50    1.50    --   48.00  82.00   0.00  252
  4  \w     11.00 137.00   0.50    1.50    --   48.00  82.00   0.00  252
  5  \w     15.00 141.00   0.50    1.50    --   52.00  82.00 120.52  252
  6  \w     23.00 149.00   0.50    1.50    --   60.00  82.00-174.03  252
  7  \w     23.00 149.00   0.50    1.50    --   60.00  82.00-113.17  252
  8  \w     31.00 157.00   0.50    1.50    --   68.00  82.00 -71.80  252
  9  \w     39.00 165.00   0.50    1.50    --   76.00  81.00 101.84  252
 10  \w     39.00 165.00   0.50    1.50    --   76.00  82.00 -19.73  252
 11  \w     39.00 165.00   0.50    1.50    --   76.00  82.00  20.99  252
 12  \w     39.00 165.00   0.50    1.50    --   76.00  82.00  51.20  252
 13  \w     43.00 153.50   0.50    1.50    --   80.00  81.00-114.03  221
 14  \w     43.00 169.00   0.50    1.50    --   80.00  82.00 -68.64  252
 15  \w     43.00 169.00   0.50    1.50    --   80.00  81.00-152.96  252
 16  \w     47.00 173.00   0.50    1.50    --   84.00  82.00 171.26  252
 17  \w     47.00 173.00   0.50    1.50    --   84.00  82.00 171.26  252
 18  \w     51.00 177.00   0.50    1.50    --   88.00  82.00 115.60  252
 19  \w     51.00 177.00   0.50    1.50    --   88.00  81.00 139.14  252
 20  \w      6.00 133.00   0.50    1.50    --   95.80 -82.00 -60.00  254
 21  \w      6.00 126.00   0.50    1.50    --   95.80 -61.00-180.00  240
 22  \w      6.00 133.00   0.50    1.50    --   95.80 -82.00 120.00  254
 23  \w     63.00 185.00   0.50    1.50    --   95.80  39.00-126.43  244
 24  \w     60.00 185.00   0.50    1.50    --   95.80  77.00  90.00  250
 25  \w      6.00 133.00   0.50    1.50    --   95.80 -82.00  30.00  254
 26  \w     58.00 185.00   0.50    1.50    --   95.80  82.00 -30.00  254
 27  \w     62.00 185.00   0.50    1.50    --   95.80  37.00 -91.46  246
 28  \w     65.00 185.00   0.50    1.50    --   95.80  61.00 -30.00  240
 29  \w     63.00 185.00   0.50    1.50    --   95.80  67.00  23.22  244
 30  \w      6.00 133.00   0.50    1.50    --   95.80 -82.00  60.00  254
 31  \w     58.00 185.00   0.50    1.50    --   95.80  82.00-120.00  254
 32  \w      6.00 133.00   0.50    1.50    --   95.80 -82.00-150.00  254
 33  \w     65.00 185.00   0.50    1.50    --   95.80  57.00  86.50  240
 34  \w     58.00 185.00   0.50    1.50    --   95.80  82.00  30.00  254
 35  \w     58.00 185.00   0.50    1.50    --   95.80  82.00 120.00  254
 36  \w     60.00 185.00   0.50    1.50    --   95.80  77.00 -90.00  250
 37  \w    -35.00  77.00   0.50    0.50    --    0.00  77.00 -60.00  224
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1126572000
_diffrn_orient_matrix_UB_12      -0.0020365000
_diffrn_orient_matrix_UB_13      0.0473938000
_diffrn_orient_matrix_UB_21      -0.0375387000
_diffrn_orient_matrix_UB_22      -0.0621932000
_diffrn_orient_matrix_UB_23      0.0405601000
_diffrn_orient_matrix_UB_31      0.0052528000
_diffrn_orient_matrix_UB_32      -0.0596032000
_diffrn_orient_matrix_UB_33      -0.0550376000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            172919
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.575
_diffrn_reflns_theta_min         2.386
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    7.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       block
_exptl_crystal_F_000             2156
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.395
_refine_diff_density_min         -1.657
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1080
_refine_ls_number_reflns         18656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+10.5877P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1184
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17893
_reflns_number_total             18656
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01675_si_003.cif
_cod_data_source_block           sj-lzh-cido
_cod_depositor_comments
;

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C77 H82 Cl6 O6 S24'
_cod_original_formula_weight         2085.56
_cod_original_formula_moiety         '2(C37 H38 O3 S12), 3(C H2 Cl2)'
_cod_original_formula_units_Z            2
_cod_database_code               4034493
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.317
_shelx_estimated_absorpt_t_min   0.260
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2. Rigid bond restraints
 C02N
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C02V
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C02U
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C02X
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C02I
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C02Q
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C02G
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C02P
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Others
 Fixed Sof: O6(0.5) H6(0.5) O3(0.5) H3(0.5) O4(0.5) H4(0.5) O2(0.5) H2(0.5)
 O7(0.5) H7(0.5) O1(0.5) H1(0.5) O5(0.5) H5(0.5) O8(0.5) H8(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C02G(H3AA,HF), C02I(H5AA,HI), C02N(H02P,H02Q), C02P(H8AA,HN), C02Q(H9AA,HO),
 C02U(H02U,H02V), C02V(H02W,H02X), C02X(H02Z,HV), C02Z(H2BA,HY), C034(H03C,
 H03D), C036(H03A,H03B)
4.b Aromatic/amide H refined with riding coordinates:
 C01D(H01D), C01K(H01K), C01O(H01O), C01X(H01X), C020(H020), C021(H021)
4.c Idealised Me refined as rotating group:
 C023(H02A,H02B,H02C), C025(H0AA,H,HA), C027(H02D,H02E,H02F), C02C(H02G,H02H,
 H02I), C02D(H1AA,HB,HC), C02E(H02J,H02K,H02L), C02F(H2AA,HD,HE), C02H(H4AA,HG,
 HH), C02J(H02M,H02N,H02O), C02K(H6AA,HJ,HK), C02L(H7AA,HL,HM), C02R(H0BA,HP,
 HQ), C02S(H1BA,HR,HS), C02T(H02R,H02S,H02T), C02W(H02Y,HT,HU), C02Y(H02,HW,HX)
4.d Idealised tetrahedral OH refined as rotating group:
 O10(H10), O9(H9), O6(H6), O3(H3), O4(H4), O2(H2), O7(H7), O1(H1), O5(H5),
 O8(H8)
;
_shelx_res_checksum              2147
_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 2.647
_oxdiff_exptl_absorpt_empirical_full_min 0.758