Microwave-assisted rapid synthesis of chiral oxazolines.
Deng, Haowen; Wang, Jianshe; He, Wei; Ye, Yang; Bai, Renren; Zhang, Xuelei; Ye, Xiang-Yang; Xie, Tian; Hui, Zi; Organic & biomolecular chemistry 21 (2023) 2312–2319; doi:10.1039/d2ob02192g

data_7159068
_publ_section_title
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 Microwave-assisted rapid synthesis of chiral oxazolines.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2312
_journal_page_last               2319
_journal_paper_doi               10.1039/d2ob02192g
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C16 H12 I N O'
_chemical_formula_sum            'C16 H12 I N O'
_chemical_formula_weight         361.17
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-25
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_audit_update_record
;
2022-10-18 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.896(5)
_cell_length_b                   10.615(12)
_cell_length_c                   26.62(3)
_cell_measurement_reflns_used    1944
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.550
_cell_measurement_theta_min      2.445
_cell_volume                     1383(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9381
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.507
_diffrn_reflns_theta_min         1.530
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.305
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1075 before and 0.0446 after correction.
The Ratio of minimum to maximum transmission is 0.8149.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0346
_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^)+(0.0170P)^2^+0.1140P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0581
_refine_ls_wR_factor_ref         0.0695
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                2136
_reflns_number_total             3461
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02192g2.cif
_cod_data_source_block           mo220823a_pl
_cod_depositor_comments          'Adding full bibliography for 7159068.cif.'
_cod_database_code               7159068
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.802
_shelx_estimated_absorpt_t_min   0.596
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.96(3)
 0.04(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Ternary CH refined with riding coordinates:
 C2(H2), C10(H10)
3.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C4(H4), C12(H12), C14(H14), C13(H13), C7(H7), C6(H6), C5(H5)
;
_shelx_res_checksum              89244
_olex2_submission_special_instructions 'No special instructions were received'