Stereospecific Synthesis of Substituted Aziridines by a Crystal-to-Crystal Photodenitrogenation of Δ(2)-1,2,3-Triazolines.
Chung, Tim S.; Lopez, Steven A.; Houk, K. N.; Garcia-Garibay, Miguel A; Organic letters 17 (2015) 4568–4571; doi:10.1021/acs.orglett.5b02290

data_1534118
_publ_section_title
;
 Stereospecific Synthesis of Substituted Aziridines by a
 Crystal-to-Crystal Photodenitrogenation of \D(2)-1,2,3-Triazolines.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4568
_journal_page_last               4571
_journal_paper_doi               10.1021/acs.orglett.5b02290
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_sum            'C20 H18 F3 N3 O2'
_chemical_formula_weight         389.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.6564(6)
_cell_length_b                   5.4719(2)
_cell_length_c                   39.3699(15)
_cell_measurement_reflns_used    3605
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.72
_cell_measurement_theta_min      4.49
_cell_volume                     3588.3(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_av_unetI/netI     0.1426
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            18835
_diffrn_reflns_point_group_measured_fraction_full 0.902
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.107
_diffrn_reflns_theta_min         2.244
_diffrn_source                   'I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    0.988
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       needle
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
; 
 Flack x determined using 1760 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.31(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         5900
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0719
_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^)+(0.0764P)^2^+1.9058P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1785
_refine_ls_wR_factor_ref         0.1912
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_full    0.807
_reflns_Friedel_fraction_max     0.785
_reflns_number_gt                4825
_reflns_number_total             5900
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02290_si_002.cif
_cod_data_source_block           gg1503sa
_cod_database_code               1534118
_shelx_estimated_absorpt_t_min   0.638
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2014/6
_shelx_res_checksum              32169
_shelx_hkl_checksum              60661