A transition-metal-free multicomponent reaction towards constructing chiral 2H-1,4-benzoxazine scaffolds
Zhu, Lixiang; Ren, Xiaoyu; Du, Juan; Wu, Jia-Hong; Tan, Jian-Ping; Che, Jixing; Pan, Jianke; Wang, Tianli; Green Chemistry 22 (2020) 7506–7512; doi:10.1039/D0GC02134B

data_7241224
_publ_section_title
;
 A transition-metal-free multicomponent reaction towards constructing
 chiral 2H-1,4-benzoxazine scaffolds
;
_journal_issue                   21
_journal_name_full               'Green Chemistry'
_journal_page_first              7506
_journal_page_last               7512
_journal_paper_doi               10.1039/D0GC02134B
_journal_volume                  22
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H17 N O2'
_chemical_formula_sum            'C21 H17 N O2'
_chemical_formula_weight         315.36
_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             2019-06-03
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2020-05-18 deposited with the CCDC.	2020-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.61101(18)
_cell_length_b                   10.7261(2)
_cell_length_c                   15.5952(3)
_cell_measurement_reflns_used    3753
_cell_measurement_temperature    296.63(16)
_cell_measurement_theta_max      71.4930
_cell_measurement_theta_min      4.9450
_cell_volume                     1607.69(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.63(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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    -53.00  31.00   1.00    1.00    --  -36.29  57.00 -60.00   84
  2  \w   -106.00  33.00   1.00    1.00    --  -36.29   0.00 -60.00  139
  3  \w      1.00  75.00   1.00    1.00    --   36.29 -99.00-120.00   74
  4  \w     88.00 173.00   1.00    1.61    --  106.21  61.00   0.00   85
  5  \w     79.00 174.00   1.00    1.61    --  106.21  77.00  90.00   95
  6  \w     37.00 109.00   1.00    1.61    --  106.21 -94.00   0.00   72
  7  \w     89.00 175.00   1.00    1.61    --  106.21  45.00 120.00   86
  8  \w     39.00 124.00   1.00    1.61    --  106.21 -61.00 150.00   85
  9  \w     68.00 177.00   1.00    1.61    --  106.21  15.00-120.00  109
 10  \w     37.00 109.00   1.00    1.61    --  106.21 -94.00-120.00   72
 11  \w     57.00 150.00   1.00    1.61    --  106.21 178.00  30.00   93
 12  \w   -104.00 -10.00   1.00    1.00    --  -36.29 -77.00-150.00   94
 13  \w    -31.00  22.00   1.00    1.00    --   36.29 -57.00  60.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, 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      -0.0829550000
_diffrn_orient_matrix_UB_12      -0.1227356000
_diffrn_orient_matrix_UB_13      0.0044948000
_diffrn_orient_matrix_UB_21      -0.0018229000
_diffrn_orient_matrix_UB_22      -0.0066307000
_diffrn_orient_matrix_UB_23      -0.0986731000
_diffrn_orient_matrix_UB_31      0.1371814000
_diffrn_orient_matrix_UB_32      -0.0742450000
_diffrn_orient_matrix_UB_33      0.0014005000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8852
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.704
_diffrn_reflns_theta_min         5.004
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.162
_refine_ls_abs_structure_details
;
 Flack x determined using 1167 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0726
_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^)+(0.1206P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1591
_refine_ls_wR_factor_ref         0.1640
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                2935
_reflns_number_total             3096
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc02134b2.cif
_cod_data_source_block           wtl-zlx-p1
_cod_depositor_comments
'Adding full bibliography for 7241224--7241225.cif.'
_cod_original_cell_volume        1607.68(6)
_cod_database_code               7241224
_reflns_odcompleteness_completeness 99.94
_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 N(H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008), C009(H009)
2.b Aromatic/amide H refined with riding coordinates:
 N003(H003), C005(H005), C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E),
 C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O)
;
_shelx_res_checksum              44806
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-06-03
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.606
_oxdiff_exptl_absorpt_empirical_full_min 0.776