Organocatalytic enantioselective [2 + 4]-annulation of γ-substituted allenoates with <i>N</i>-acyldiazenes for the synthesis of optically active 1,3,4-oxadiazines.
Guo, Xing; Chen, Xuling; Cheng, Yuyu; Chang, Xiaoyong; Li, Xuechen; Li, Pengfei; Organic & biomolecular chemistry 19 (2021) 1727–1731; doi:10.1039/d0ob02508a

data_7157855
_publ_section_title
;
 Organocatalytic enantioselective [2 + 4]-annulation of \g-substituted
 allenoates with <i>N</i>-acyldiazenes for the synthesis of optically
 active 1,3,4-oxadiazines.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1727
_journal_page_last               1731
_journal_paper_doi               10.1039/d0ob02508a
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H23 Cl N2 O3'
_chemical_formula_sum            'C26 H23 Cl N2 O3'
_chemical_formula_weight         446.91
_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     dual
_audit_creation_date             2020-01-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-26 deposited with the CCDC.	2021-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.234(3)
_cell_length_b                   14.235(5)
_cell_length_c                   30.529(12)
_cell_measurement_reflns_used    9075
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.40
_cell_volume                     4447(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'BrukerD8 venture microsource'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22253
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.288
_diffrn_reflns_theta_min         2.396
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0866 before and 0.0649 after correction. The Ratio of minimum to maximum transmission is 0.9299. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 3613 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_extinction_coef       0.0025(4)
_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   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     580
_refine_ls_number_reflns         10880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0291P)^2^+1.2386P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0958
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                9427
_reflns_number_total             10880
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02508a2.cif
_cod_data_source_block           cxy1118_0m
_cod_depositor_comments
'Adding full bibliography for 7157855--7157856.cif.'
_cod_original_cell_volume        4448(3)
_cod_database_code               7157855
_shelx_shelxl_version_number     2018/3
_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), C32(H32)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C23(H23A,H23B), C33(H33A,H33B), C43(H43A,H43B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C25(H25), C26(H26), C28(H28),
  C29(H29), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), C41(H41),
 C46(H46), C47(H47), C48(H48), C49(H49), C50(H50), C51(H51), C52(H52)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C44(H44A,H44B,H44C)
;
_olex2_submission_special_instructions 'No special instructions were received'