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_7128140
_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_formula_moiety         'C20 H21 N3 O5'
_chemical_formula_sum            'C20 H21 N3 O5'
_chemical_formula_weight         383.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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                 100.128(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3393(2)
_cell_length_b                   21.3081(6)
_cell_length_c                   11.1096(4)
_cell_measurement_reflns_used    4857
_cell_measurement_temperature    292.8(4)
_cell_measurement_theta_max      71.2760
_cell_measurement_theta_min      4.1420
_cell_volume                     1943.35(10)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.8(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.978
_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    -72.00  26.00   1.00    1.00    --  -35.62  94.00-155.00   98
  2  \w     -4.00  72.00   1.00    1.00    --   35.62 -94.00  94.00   76
  3  \w     38.00 109.00   1.00    3.83    --  107.12 -94.00  94.00   71
  4  \w    101.00 176.00   1.00    3.83    --  107.12  94.00-155.00   75
  5  \w   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00-120.00   84
  6  \w    -55.00  34.00   1.00    1.00    --  -35.62  38.00  60.00   89
  7  \w     57.00 108.00   1.00    1.00    --   35.62 178.00  90.00   51
  8  \w     57.00 108.00   1.00    1.00    --   35.62 178.00 -90.00   51
  9  \w     89.00 174.00   1.00    3.83    --  107.12  61.00-120.00   85
 10  \w     38.00  64.00   1.00    3.83    --  107.12 -30.00 -90.00   26
 11  \w    106.00 175.00   1.00    3.83    --  107.12 111.00 -60.00   69
 12  \w     60.00  86.00   1.00    3.83    --  107.12 178.00  90.00   26
 13  \w    103.00 128.00   1.00    3.83    --  107.12 -30.00 -90.00   25
 14  \w    122.00 148.00   1.00    3.83    --  107.12 178.00  90.00   26
 15  \w     56.00 113.00   1.00    3.83    --  107.12-111.00  60.00   57
 16  \w     40.00 122.00   1.00    3.83    --  107.12 -45.00 150.00   82
 17  \w     62.00  89.00   1.00    3.83    --  107.12 -95.00-180.00   27
 18  \w     90.00 176.00   1.00    3.83    --  107.12  45.00 -60.00   86
;
_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      0.0572062000
_diffrn_orient_matrix_UB_12      0.0577486000
_diffrn_orient_matrix_UB_13      -0.0641343000
_diffrn_orient_matrix_UB_21      -0.0385487000
_diffrn_orient_matrix_UB_22      -0.0344141000
_diffrn_orient_matrix_UB_23      -0.1238136000
_diffrn_orient_matrix_UB_31      -0.1745341000
_diffrn_orient_matrix_UB_32      0.0265338000
_diffrn_orient_matrix_UB_33      -0.0205036000
_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  0.0285
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9682
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.470
_diffrn_reflns_theta_min         4.150
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.793
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87681
_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    1.310
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0557
_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^)+(0.0447P)^2^+1.3070P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1388
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3117
_reflns_number_total             3721
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00600b2.cif
_cod_data_source_block           sjw-20191012
_cod_depositor_comments
'Adding full bibliography for 7128134--7128140.cif.'
_cod_database_code               7128140
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.904
_reflns_odcompleteness_completeness 99.86
_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.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              46692
_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 1.334
_oxdiff_exptl_absorpt_empirical_full_min 0.812