Formal [5+2] cycloaddition of vinylethylene carbonates to oxazol-5-(4H)-ones for the synthesis of 3,4-dihydrooxepin-2(7H)-ones.
Zhao, Hong-Wu; Du, Juan; Guo, Jia-Ming; Feng, Ning-Ning; Wang, Li-Ru; Ding, Wan-Qiu; Song, Xiu-Qing; Chemical communications (Cambridge, England) 54 (2018) 9178–9181; doi:10.1039/c8cc04584d

data_7122040
_publ_section_title
;
 Formal [5+2] cycloaddition of vinylethylene carbonates to
 oxazol-5-(4H)-ones for the synthesis of 3,4-dihydrooxepin-2(7H)-ones.
;
_journal_issue                   66
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9178
_journal_page_last               9181
_journal_paper_doi               10.1039/c8cc04584d
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C26 H22 Cl N O3'
_chemical_formula_sum            'C26 H22 Cl N O3'
_chemical_formula_weight         431.89
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-22 deposited with the CCDC.
2018-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                88.60(2)
_cell_angle_beta                 78.027(16)
_cell_angle_gamma                88.20(3)
_cell_formula_units_Z            4
_cell_length_a                   9.588(4)
_cell_length_b                   14.091(7)
_cell_length_c                   15.915(7)
_cell_measurement_reflns_used    3980
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.0
_cell_volume                     2102.0(17)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      133.15
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_av_unetI/netI     0.0770
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20434
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.019
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_min         3.014
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.9711
_exptl_absorpt_correction_T_min  0.9591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     567
_refine_ls_number_reflns         7111
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0868
_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^)+(0.0821P)^2^+6.7050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2250
_refine_ls_wR_factor_ref         0.2348
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5294
_reflns_number_total             7111
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc04584d2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7122040.cif.'
_cod_original_cell_volume        2102.0(16)
_cod_database_code               7122040
_shelx_shelxl_version_number     2014/8
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.959
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N1-H1 = N2-H2
 0.9 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C13(H13A,H13B), C27(H27A,H27B), C30(H30A,H30B),
 C39(H39A,H39B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C25(H25), C26(H26), C29(H29),
  C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C41(H41), C42(H42),
 C43(H43), C44(H44), C45(H45), C48(H48), C49(H49), C51(H51), C52(H52)
;
_shelx_res_checksum              34511
_olex2_submission_special_instructions 'No special instructions were received'