Chemo- and regioselective ring-opening of donor-acceptor oxiranes with <i>N</i>-heteroaromatics.
Sang, Ji-Wei; Xie, Ming-Sheng; Wang, Man-Man; Qu, Gui-Rong; Guo, Hai-Ming; Chemical communications (Cambridge, England) 57 (2021) 4552–4555; doi:10.1039/d1cc00600b

data_7128136
_publ_section_title
;
 Chemo- and regioselective ring-opening of donor-acceptor oxiranes with
 <i>N</i>-heteroaromatics.
;
_journal_issue                   37
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4552
_journal_page_last               4555
_journal_paper_doi               10.1039/d1cc00600b
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H19 Cl2 N3 O5'
_chemical_formula_sum            'C20 H19 Cl2 N3 O5'
_chemical_formula_weight         452.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-07-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_audit_update_record
;
2020-07-22 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.9392(5)
_cell_length_b                   15.2205(4)
_cell_length_c                   19.0810(5)
_cell_measurement_reflns_used    6146
_cell_measurement_temperature    295.28(11)
_cell_measurement_theta_max      71.1810
_cell_measurement_theta_min      4.1110
_cell_volume                     4338.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.28(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.977
_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     -5.00  25.00   1.00    1.00    --  -35.62  71.00  46.00   30
  2  \w   -102.00 -57.00   1.00    1.00    --  -35.62-150.00  44.00   45
  3  \w     69.00 130.00   1.00    3.39    --  107.12 -71.00 -84.00   61
  4  \w     62.00  88.00   1.00    3.39    --  107.12 -50.00  76.00   26
  5  \w    119.00 145.00   1.00    3.39    --  107.12  71.00  46.00   26
  6  \w    117.00 161.00   1.00    3.39    --  107.12  50.00-137.00   44
  7  \w     40.00 115.00   1.00    3.39    --  107.12-123.00-153.00   75
  8  \w   -103.00 -43.00   1.00    1.00    --  -35.62 -57.00  90.00   60
  9  \w    -60.00 -35.00   1.00    1.00    --  -35.62-178.00 -90.00   25
 10  \w   -108.00 -77.00   1.00    1.00    --  -35.62-178.00 -90.00   31
 11  \w     10.00  74.00   1.00    1.00    --   35.62 -99.00 -90.00   64
 12  \w    101.00 175.00   1.00    3.39    --  107.12 111.00-120.00   74
 13  \w     38.00 109.00   1.00    3.39    --  107.12 -95.00  60.00   71
 14  \w     78.00 110.00   1.00    3.39    --  107.12 -95.00-120.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0392784000
_diffrn_orient_matrix_UB_12      0.0534796000
_diffrn_orient_matrix_UB_13      -0.0614124000
_diffrn_orient_matrix_UB_21      -0.0948599000
_diffrn_orient_matrix_UB_22      -0.0302646000
_diffrn_orient_matrix_UB_23      0.0204616000
_diffrn_orient_matrix_UB_31      -0.0096841000
_diffrn_orient_matrix_UB_32      0.0804180000
_diffrn_orient_matrix_UB_33      0.0482634000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13129
_diffrn_reflns_point_group_measured_fraction_full 0.910
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.536
_diffrn_reflns_theta_min         3.715
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.011
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 1918 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.44(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         7494
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0769
_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^)+(0.1556P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2086
_refine_ls_wR_factor_ref         0.2268
_reflns_Friedel_coverage         0.632
_reflns_Friedel_fraction_full    0.803
_reflns_Friedel_fraction_max     0.768
_reflns_number_gt                6247
_reflns_number_total             7494
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00600b2.cif
_cod_data_source_block           sjw-20200721
_cod_depositor_comments
'Adding full bibliography for 7128134--7128140.cif.'
_cod_database_code               7128136
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_shelx_estimated_absorpt_t_max   0.773
_shelx_estimated_absorpt_t_min   0.696
_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
2. Restrained distances
 C16-C17
 1.51 with sigma of 0.02
 C36-C37
 1.5 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C34(H34), C14(H14), C7(H7), C27(H27)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C39(H39A,H39B), C16(H16A,H16B), C36(H36A,H36B)
3.c Me refined with riding coordinates:
 C17(H17A,H17B,H17C)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C25(H25), C6(H6), C23(H23), C22(H22), C5(H5), C29(H29), C13(H13),
 C12(H12), C10(H10), C11(H11), C30(H30), C31(H31), C32(H32)
3.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C40(H40A,H40B,H40C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              18439
_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 3.140
_oxdiff_exptl_absorpt_empirical_full_min 0.497