Catalyst-free reaction of 2-(4<i>H</i>-benzo[<i>d</i>][1,3]oxazin-4-yl)acrylates: synthesis of 1,2-dihydroquinolines and 2,3-dihydropyrroles.
Wang, Tao; Lu, Zhongyue; Li, Pengfei; Chemical communications (Cambridge, England) 60 (2024) 6933–6936; doi:10.1039/d4cc02156h

data_7133184
_publ_section_title
;
 Catalyst-free reaction of
 2-(4<i>H</i>-benzo[<i>d</i>][1,3]oxazin-4-yl)acrylates: synthesis of
 1,2-dihydroquinolines and 2,3-dihydropyrroles.
;
_journal_issue                   54
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6933
_journal_page_last               6936
_journal_paper_doi               10.1039/d4cc02156h
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H21 N O4'
_chemical_formula_sum            'C26 H21 N O4'
_chemical_formula_weight         411.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-16
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-04-03 deposited with the CCDC.	2024-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.031(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.9055(4)
_cell_length_b                   21.4299(11)
_cell_length_c                   27.6189(15)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      56.89
_cell_measurement_theta_min      2.27
_cell_volume                     4084.6(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2014'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON III area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_number            15953
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         56.917
_diffrn_reflns_theta_min         1.392
_diffrn_source                   'microfocus Metaljet'
_diffrn_source_current           3.0
_diffrn_source_power             0.20958
_diffrn_source_type              'Incoatec Metaljet'
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.466
_exptl_absorpt_correction_T_max  0.764
_exptl_absorpt_correction_T_min  0.568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1091 before and 0.0677 after correction.
 
For component 2:
 wR2(int) was 0.1163 before and 0.0693 after correction.
 The Ratio of minimum to maximum transmission is 0.85.

Final HKLF 4 output contains 72600 reflections, Rint = 0.0524
 (56652 with I > 3sig(I), Rint = 0.0498)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 5307 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(13)
_refine_ls_extinction_coef       0.0038(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1122
_refine_ls_number_reflns         15953
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0753
_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^)+(0.0933P)^2^+8.6690P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2086
_refine_ls_wR_factor_ref         0.2168
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                13057
_reflns_number_total             15953
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02156h2.cif
_cod_data_source_block           cxy5064_0m_4
_cod_depositor_comments
'Adding full bibliography for 7133184--7133186.cif.'
_cod_database_code               7133184
_shelx_shelxl_version_number     2019/2
_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:
 C3(H3), C29(H29), C55(H55), C81(H81)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C44(H44A,H44B), C70(H70A,H70B), C96(H96A,H96B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C6(H6), C21(H21), C22(H22), C23(H23), C17(H17), C16(H16),
 C15(H15), C14(H14), C13(H13), C25(H25), C24(H24), C10(H10), C9(H9), C49(H49),
 C48(H48), C47(H47), C32(H32), C33(H33), C34(H34), C39(H39), C43(H43), C42(H42),
  C41(H41), C40(H40), C35(H35), C36(H36), C51(H51), C50(H50), C75(H75),
 C74(H74), C73(H73), C58(H58), C59(H59), C60(H60), C69(H69), C68(H68), C67(H67),
  C66(H66), C65(H65), C61(H61), C62(H62), C77(H77), C76(H76), C86(H86),
 C85(H85), C84(H84), C99(H99), C100(H100), C101(H101), C88(H88), C87(H87),
 C95(H95), C94(H94), C93(H93), C92(H92), C91(H91), C103(H103), C102(H102)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C52(H52A,H52B,H52C), C78(H78A,H78B,H78C), C104(H10A,H10B,
 H10C)
;
_shelx_res_checksum              103
_shelx_hkl_checksum              97643
_olex2_submission_special_instructions 'No special instructions were received'