Oxaazabicyclooctene Oxides, Another Type of Bridgehead Nitrones: Diastereoselective Assembly from Acetylene gas, Ketones and Hydroxyl Amine.
Schmidt, Elena Yu; Tatarinova, Inna V.; Ushakov, Igor A.; Vashchenko, Alexander Valentine; Trofimov, Boris A.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00742

data_4038336
_publ_section_title
;
 Oxaazabicyclooctene Oxides, Another Type of Bridgehead Nitrones:
 Diastereoselective Assembly from Acetylene gas, Ketones and Hydroxyl
 Amine.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00742
_journal_year                    2020
_chemical_formula_moiety         'C25 H23 N O2, 0.5(H2 O)'
_chemical_formula_sum            'C25 H24 N O2.5'
_chemical_formula_weight         378.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-05 # Formatted by publCIF

;
_cell_angle_alpha                102.72(2)
_cell_angle_beta                 92.22(4)
_cell_angle_gamma                109.91(3)
_cell_formula_units_Z            4
_cell_length_a                   10.384(8)
_cell_length_b                   10.986(8)
_cell_length_c                   19.425(14)
_cell_measurement_reflns_used    871
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.5
_cell_volume                     2017(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_device_type  'Bruker  D8 Venture'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_monochromator  No
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            71221
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.170
_diffrn_reflns_theta_min         2.166
_diffrn_source                   IuS
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0970 before and 0.0566 after correction.
The Ratio of minimum to maximum transmission is 0.9222.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       prism
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         8164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0476P)^2^+0.7664P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5200
_reflns_number_total             8164
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00742_si_002.cif
_cod_data_source_block           a_a
_cod_depositor_comments
;

2025-07-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C25 H23 N O2), H2 O'
_cod_original_formula_sum        'C50 H48 N2 O5'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     756.90
_cod_database_code               4038336
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.985
_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, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Ternary CH refined with riding coordinates:
 C12(H12), C40(H40)
2.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C39(H39A,H39B), C41(H41A,H41B)
2.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28), C33(H33), C34(H34), C35(H35), C37(H37), C38(H38),
 C43(H43), C44(H44), C45(H45), C46(H46), C47(H47), C49(H49), C50(H50)
2.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C48(H48A,H48B,H48C)
;
_shelx_res_checksum              59996
_shelx_hkl_checksum              28011
_olex2_submission_special_instructions 'No special instructions were received'