Stereoselective Syntheses of Highly Functionalized Imidazolidines and Oxazolidines via Ring-Opening-Cyclization of Activated Aziridines and Epoxides with Amines and Aldehydes.
Tarannum, Saima; Sk, Sahid; Das, Subhomoy; Wani, Imtiyaz Ahmad; Ghorai, Manas K.; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02278

data_4037654
_publ_section_title
;
 Stereoselective Syntheses of Highly Functionalized Imidazolidines and
 Oxazolidines via Ring-Opening-Cyclization of Activated Aziridines and
 Epoxides with Amines and Aldehydes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02278
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C28 H26 N2 O2 S'
_chemical_formula_sum            'C28 H26 N2 O2 S'
_chemical_formula_weight         454.56
_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             2019-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6558(2)
_cell_length_b                   11.2377(2)
_cell_length_c                   19.3781(4)
_cell_measurement_reflns_used    5539
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.318
_cell_measurement_theta_min      2.181
_cell_volume                     2320.46(8)
_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_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            37890
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.318
_diffrn_reflns_theta_min         2.181
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details
;
 Flack x determined using 2383 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0285
_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^)+(0.0544P)^2^+0.2661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0893
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                5539
_reflns_number_total             5746
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02278_si_002.cif
_cod_data_source_block           27marb_0m
_cod_depositor_comments
;

2020-10-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '0.5(C28 H26 N2 O2 S)'
_cod_original_formula_sum        'C14 H13 N O S0.50'
_cod_original_formula_units_Z    8
_cod_original_formula_weight     227.28
_cod_database_code               4037654
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.967
_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:
 C00E(H00E), C00K(H00K)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00D,H00H)
2.c Aromatic/amide H refined with riding coordinates:
 C006(H006), C007(H007), C008(H008), C00A(H00A), C00B(H00B), C00C(H00C),
 C00F(H00F), C00G(H00G), C00I(H00I), C00J(H00J), C00L(H00L), C00N(H00N),
 C00O(H00O), C00P(H00P), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U),
 C00W(H00W)
2.d Idealised Me refined as rotating group:
 C00X(H00M,H00Q,H00V)
;
_shelx_res_checksum              31637
_shelx_hkl_checksum              73847
_olex2_submission_special_instructions 'No special instructions were received'