Stereodivergent synthesis of β-iodoenol carbamates with CO2via photocatalysis
Wang, Lu; Shi, Fuxing; Qi, Chaorong; Xu, Wenjie; Xiong, Wenfang; Kang, Bangxiong; Jiang, Huanfeng; Chemical Science 12 (2021) 11821–11830; doi:10.1039/D1SC03366B

data_1564663
_publ_section_title
;
 Stereodivergent synthesis of \b-iodoenol carbamates with CO2via
 photocatalysis
;
_journal_issue                   35
_journal_name_full               'Chemical Science'
_journal_page_first              11821
_journal_page_last               11830
_journal_paper_doi               10.1039/D1SC03366B
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C0.5 H Cl, 2(C20.5 H17.5 N0.5 O)'
_chemical_formula_sum            'C41.5 H36 Cl N O2'
_chemical_formula_weight         616.16
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-09-18
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5924)
;
_audit_update_record
;
2020-10-30 deposited with the CCDC.	2021-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.5244(15)
_cell_length_b                   25.6507(14)
_cell_length_c                   10.3465(6)
_cell_measurement_reflns_used    5126
_cell_measurement_temperature    100.01(11)
_cell_measurement_theta_max      27.6200
_cell_measurement_theta_min      2.2660
_cell_volume                     6508.7(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS n/a (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.882
_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     -9.00  25.00   1.00   12.00    --  -11.59 -99.00  60.00   34
  2  \w      6.00  62.00   1.00   12.00    --  -11.59  57.00-150.00   56
  3  \w      1.00  57.00   1.00   12.00    --   11.74  37.00-180.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0254673000
_diffrn_orient_matrix_UB_12      0.0105290000
_diffrn_orient_matrix_UB_13      -0.0195168000
_diffrn_orient_matrix_UB_21      0.0103862000
_diffrn_orient_matrix_UB_22      -0.0255559000
_diffrn_orient_matrix_UB_23      -0.0087612000
_diffrn_orient_matrix_UB_31      -0.0090218000
_diffrn_orient_matrix_UB_32      0.0003108000
_diffrn_orient_matrix_UB_33      -0.0650993000
_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  0.0698
_diffrn_reflns_av_unetI/netI     0.0929
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            25236
_diffrn_reflns_point_group_measured_fraction_full 0.836
_diffrn_reflns_point_group_measured_fraction_max 0.684
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.587
_diffrn_reflns_theta_min         2.279
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             2600
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.069
_refine_diff_density_min         -1.242
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 2302 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     824
_refine_ls_number_reflns         12508
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0816
_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^)+(0.1101P)^2^+3.3020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1976
_refine_ls_wR_factor_ref         0.2232
_reflns_Friedel_coverage         0.473
_reflns_Friedel_fraction_full    0.652
_reflns_Friedel_fraction_max     0.464
_reflns_number_gt                9257
_reflns_number_total             12508
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03366b2.cif
_cod_data_source_block           w-1
_cod_original_formula_sum        'C41.50 H36 Cl N O2'
_cod_database_code               1564663
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.980
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Rigid bond restraints
 C8B, C9B, C10B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C8B \\sim C9B \\sim C10B: within 2A with sigma of 0.002 and sigma for terminal
atoms of 0.004 within 2A
4.a Secondary CH2 refined with riding coordinates:
 C31B(H31A,H31B), C33B(H33A,H33B), C39(H39A,H39B), C37(H37A,H37B), C1S(H1SA,
 H1SB)
4.b Aromatic/amide H refined with riding coordinates:
 C26(H26), C36(H36), C28(H28), C27(H27), C34(H34), C20(H20), C21(H21),
 C24(H24), C13(H13), C29(H29), C17(H17), C30(H30), C16(H16), C40B(H40D), C8(H8),
  C27B(H27B), C33(H33), C36B(H36B), C14(H14), C11(H11), C22(H22), C7(H7),
 C9(H9), C28B(H28B), C24B(H24B), C32(H32), C35(H35), C22B(H22B), C23(H23),
 C15(H15), C37B(H37C), C10(H10), C25B(H25B), C26B(H26B), C39B(H39C), C38B(H38D),
  C021(H021), C17B(H17B), C21B(H21B), C13B(H13B), C19B(H19B), C16B(H16B),
 C15B(H15B), C20B(H20B), C14B(H14B), C11B(H11B), C10B(H10B), C7B(H7B), C9B(H9B),
  C8B(H8B)
4.c Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C34B(H34A,H34B,H34C), C32B(H32A,H32B,H32C), C38(H38A,
 H38B,H38C)
;
_shelx_res_checksum              53000
_shelx_hkl_checksum              64420
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.150
_oxdiff_exptl_absorpt_empirical_full_min 0.806