Asymmetric [3 + 2] photocycloadditions of cyclopropylamines with electron-rich and electron-neutral olefins
Dai, Yating; Liang, Shuangshuang; Zeng, Guangkuo; Huang, Hongchun; Zhao, Xiaowei; Cao, Shanshan; Jiang, Zhiyong; Chemical Science  (2022) –; doi:10.1039/D1SC07044D

data_1566590
_publ_section_title
;
 Asymmetric [3 + 2] photocycloadditions of cyclopropylamines with
 electron-rich and electron-neutral olefins
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC07044D
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H29 Cl N2 O3'
_chemical_formula_sum            'C30 H29 Cl N2 O3'
_chemical_formula_weight         501.00
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-27 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.3663(3)
_cell_length_b                   16.7129(3)
_cell_length_c                   25.3786(5)
_cell_measurement_reflns_used    4414
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      64.4760
_cell_measurement_theta_min      3.9670
_cell_volume                     5245.17(19)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -68.00 -32.00   0.50   10.00    --  -33.50 178.00  30.00   72
  2  \w    -15.00  16.00   0.50   10.00    --  -33.50  37.00-180.00   62
  3  \w   -108.00 -79.00   0.50   10.00    --  -33.50 178.00  30.00   58
  4  \w    -98.00 -19.00   0.50   10.00    --  -33.50 -57.00 -90.00  158
  5  \w     18.00 104.00   0.50   10.00    --   36.47  57.00-150.00  172
  6  \w     83.00 109.00   0.50   10.00    --   36.47  19.00  90.00   52
  7  \w      9.00  48.00   0.50   10.00    --   36.47  19.00  90.00   78
  8  \w     -3.00  65.00   0.50   10.00    --   36.47 -77.00 150.00  136
  9  \w     43.00  76.00   0.50   10.00    --   36.47 -99.00-120.00   66
 10  \w     15.00  43.00   0.50   10.00    --   36.47 -99.00  60.00   56
 11  \w     70.00 112.00   0.50   25.00    --  108.00-111.00-150.00   84
 12  \w     39.00  94.00   0.50   25.00    --  108.00 -94.00 120.00  110
 13  \w     37.00 130.00   0.50   25.00    --  108.00 -30.00-120.00  186
 14  \w    122.00 159.00   0.50   25.00    --  108.00  61.00   0.00   74
 15  \w    102.00 152.00   0.50   25.00    --  108.00 111.00 -90.00  100
 16  \w     42.00 131.00   0.50   25.00    --  108.00 -30.00 150.00  178
 17  \w     43.00 135.00   0.50   25.00    --  108.00 -77.00 -30.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0919447000
_diffrn_orient_matrix_UB_12      0.0017992000
_diffrn_orient_matrix_UB_13      0.0409761000
_diffrn_orient_matrix_UB_21      -0.0840883000
_diffrn_orient_matrix_UB_22      -0.0035866000
_diffrn_orient_matrix_UB_23      -0.0447061000
_diffrn_orient_matrix_UB_31      0.0015096000
_diffrn_orient_matrix_UB_32      -0.0920754000
_diffrn_orient_matrix_UB_33      0.0025695000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            19920
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         3.483
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.558
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       needle
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1818 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     677
_refine_ls_number_reflns         9353
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0576
_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^)+(0.0568P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1549
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                6414
_reflns_number_total             9353
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc07044d2.cif
_cod_data_source_block           20210360
_cod_original_cell_volume        5245.20(18)
_cod_database_code               1566590
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O5N2Cl
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.912
_shelx_estimated_absorpt_t_min   0.789
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 C22-Cl1A
 1.76 with sigma of 0.02
 H2A-N2
 0.86 with sigma of 0.02
 N2'-H2'A
 0.86 with sigma of 0.02
 N1'-H1'A
 0.86 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1') = Uanis(Cl)
Uanis(Cl1) = Uanis(Cl1A)
4. Others
 Sof(H18')=Sof(Cl)=1-FVAR(1)
 Sof(H22')=Sof(Cl1')=FVAR(1)
 Sof(H18)=Sof(Cl1A)=1-FVAR(2)
 Sof(H22)=Sof(Cl1)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C12(H12), C12'(H12')
5.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C13'(H13C,H13D), C14'(H14C,
 H14D), C15'(H15C,H15D)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C10(H10), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C25(H25), C26(H26), C28(H28), C1'(H1'), C2'(H2'),
  C3'(H3'), C4'(H4'), C7'(H7'), C9'(H9'), C10'(H10'), C18'(H18'), C19'(H19'),
 C20'(H20'), C21'(H21'), C22'(H22'), C25'(H25'), C26'(H26'), C28'(H28')
5.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C29'(H29D,H29E,H29F), C30'(H30D,
 H30E,H30F)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.136
_oxdiff_exptl_absorpt_empirical_full_min 0.870