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_7128138
_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         'C22 H25 N3 O5'
_chemical_formula_sum            'C22 H25 N3 O5'
_chemical_formula_weight         411.45
_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
_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                61.499(7)
_cell_angle_beta                 78.529(5)
_cell_angle_gamma                86.047(5)
_cell_formula_units_Z            2
_cell_length_a                   9.5779(5)
_cell_length_b                   11.3128(7)
_cell_length_c                   11.8490(8)
_cell_measurement_reflns_used    5472
_cell_measurement_temperature    290(4)
_cell_measurement_theta_max      71.2380
_cell_measurement_theta_min      4.7180
_cell_volume                     1105.24(14)
_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      290(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_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    -77.00  17.00   1.00    1.00    --  -35.62 103.00  58.00   94
  2  \w     37.00 111.00   1.00    1.00    --  107.12-103.00 -43.00   74
  3  \w    101.00 177.00   1.00    1.00    --  107.12 103.00  58.00   76
  4  \w   -108.00 -35.00   1.00    1.00    --  -35.62-178.00 -60.00   73
  5  \w     17.00 105.00   1.00    1.00    --   35.62  38.00 -60.00   88
  6  \w      1.00  75.00   1.00    1.00    --   35.62 -99.00-180.00   74
  7  \w    -34.00  55.00   1.00    1.00    --   35.62 -38.00  60.00   89
  8  \w      9.00 103.00   1.00    1.00    --   35.62  77.00-180.00   94
  9  \w    -36.00  65.00   1.00    1.00    --   35.62 -19.00 -60.00  101
 10  \w      5.00  77.00   1.00    1.00    --   35.62-103.00 -43.00   72
 11  \w     80.00 175.00   1.00    1.00    --  107.12  77.00 120.00   95
 12  \w     37.00 113.00   1.00    1.00    --  107.12-111.00 -90.00   76
 13  \w     39.00 125.00   1.00    1.00    --  107.12 -45.00   0.00   86
 14  \w     90.00 176.00   1.00    1.00    --  107.12  45.00  90.00   86
 15  \w     39.00 125.00   1.00    1.00    --  107.12 -45.00 -90.00   86
 16  \w     40.00 124.00   1.00    1.00    --  107.12 -45.00  90.00   84
 17  \w     73.00 108.00   1.00    1.00    --  107.12 -95.00 -60.00   35
 18  \w     98.00 175.00   1.00    1.00    --  107.12  45.00  30.00   77
 19  \w     40.00  90.00   1.00    1.00    --  107.12 -45.00-180.00   50
 20  \w     55.00 110.00   1.00    1.00    --  107.12 -95.00 120.00   55
 21  \w     58.00 110.00   1.00    1.00    --  107.12 -95.00  30.00   52
 22  \w     94.00 120.00   1.00    1.00    --  107.12 -77.00 120.00   26
 23  \w    111.00 138.00   1.00    1.00    --  107.12  61.00-150.00   27
 24  \w     98.00 165.00   1.00    1.00    --  107.12  61.00 -30.00   67
;
_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      0.0091164000
_diffrn_orient_matrix_UB_12      -0.0463813000
_diffrn_orient_matrix_UB_13      0.1434416000
_diffrn_orient_matrix_UB_21      0.0397333000
_diffrn_orient_matrix_UB_22      -0.1415854000
_diffrn_orient_matrix_UB_23      0.0184222000
_diffrn_orient_matrix_UB_31      0.1590578000
_diffrn_orient_matrix_UB_32      0.0428522000
_diffrn_orient_matrix_UB_33      -0.0422708000
_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  0.0193
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8787
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.479
_diffrn_reflns_theta_min         4.324
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64926
_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    1.236
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.048(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4210
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0619
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1102P)^2^+0.3499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1864
_refine_ls_wR_factor_ref         0.1923
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3715
_reflns_number_total             4210
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00600b2.cif
_cod_data_source_block           sjw-20200720
_cod_depositor_comments
'Adding full bibliography for 7128134--7128140.cif.'
_cod_original_cell_volume        1105.24(13)
_cod_database_code               7128138
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.911
_reflns_odcompleteness_completeness 99.95
_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
 C19-C20
 1.55 with sigma of 0.02
3. Rigid bond restraints
 C19, C20
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C19 \\sim C20: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
5.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14)
5.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C19(H19A,H19B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
5.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
;
_shelx_res_checksum              11214
_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 1.591
_oxdiff_exptl_absorpt_empirical_full_min 0.503