Diastereoselective desymmetrization reactions of prochiral para-quinamines with cyclopropenes generated in situ: access to fused hydroindol-5-one scaffolds.
Lodhi, Rajni; Prakash, Meher; Samanta, Sampak; Organic & biomolecular chemistry 19 (2021) 7129–7133; doi:10.1039/d1ob01322j

data_7158191
_publ_section_title
;
 Diastereoselective desymmetrization reactions of prochiral
 para-quinamines with cyclopropenes generated in situ: access to fused
 hydroindol-5-one scaffolds.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7129
_journal_page_last               7133
_journal_paper_doi               10.1039/d1ob01322j
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C32 H29 N O6 S'
_chemical_formula_sum            'C32 H29 N O6 S'
_chemical_formula_weight         555.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-05 deposited with the CCDC.	2021-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.658(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7889(3)
_cell_length_b                   23.8675(5)
_cell_length_c                   11.6684(5)
_cell_measurement_reflns_used    5163
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.0060
_cell_measurement_theta_min      4.5340
_cell_volume                     2752.14(17)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0309
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.966
_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    -58.00 -17.00   1.00   15.00    --    0.00 148.00  19.00   41
  2  \w    -53.00 -28.00   1.00   15.00    --    0.00 124.00-145.00   25
  3  \w     23.00 109.00   1.00   15.00    --   54.00-124.00 135.00   86
  4  \w     56.00  81.00   1.00   15.00    --   54.00-148.00 -29.00   25
  5  \w     54.00 116.00   1.00   15.00    --  108.00-124.00 135.00   62
  6  \w     62.00  87.00   1.00   15.00    --  108.00-148.00 -29.00   25
  7  \w     91.00 169.00   1.00   15.00    --  108.00 148.00  19.00   78
  8  \w    112.00 137.00   1.00   15.00    --  108.00 124.00-145.00   25
  9  \w    -19.00  26.00   1.00   15.00    --    0.00  57.00-120.00   45
 10  \w     19.00  50.00   1.00   15.00    --    0.00  57.00 -90.00   31
 11  \w     31.00  96.00   1.00   15.00    --   54.00  38.00  60.00   65
 12  \w      0.00  75.00   1.00   15.00    --   54.00 -57.00 -60.00   75
 13  \w     27.00 123.00   1.00   15.00    --   54.00  77.00-120.00   96
 14  \w     86.00 124.00   1.00   15.00    --  108.00  63.00   0.00   38
 15  \w    100.00 138.00   1.00   15.00    --  108.00 111.00 -30.00   38
 16  \w     41.00 130.00   1.00   15.00    --  108.00 -63.00  90.00   89
 17  \w     36.00 109.00   1.00   15.00    --  108.00-111.00 -30.00   73
 18  \w    127.00 174.00   1.00   15.00    --  108.00  63.00   0.00   47
 19  \w    122.00 174.00   1.00   15.00    --  108.00  63.00-120.00   52
 20  \w     86.00 176.00   1.00   15.00    --  108.00  63.00 -90.00   90
 21  \w    131.00 163.00   1.00   15.00    --  108.00  77.00 -60.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0166507000
_diffrn_orient_matrix_UB_12      -0.0641498000
_diffrn_orient_matrix_UB_13      0.0019228000
_diffrn_orient_matrix_UB_21      0.1389866000
_diffrn_orient_matrix_UB_22      0.0053102000
_diffrn_orient_matrix_UB_23      0.1102985000
_diffrn_orient_matrix_UB_31      -0.0685005000
_diffrn_orient_matrix_UB_32      -0.0049506000
_diffrn_orient_matrix_UB_33      0.0927736000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            12957
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.223
_diffrn_reflns_theta_min         3.704
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.433
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84637
_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_density_diffrn    1.266
_exptl_crystal_description       Block
_exptl_crystal_F_000             1108
_refine_diff_density_max         0.387
_refine_diff_density_min         -1.205
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.640
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.640
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.1028
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2615
_refine_ls_wR_factor_ref         0.3020
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3541
_reflns_number_total             5159
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01322j2.cif
_cod_data_source_block           red1
_cod_depositor_comments          'Adding full bibliography for 7158191.cif.'
_cod_database_code               7158191
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 98.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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:
 C00F(H00F)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00A,H00B), C00N(H00C,H00D), C00W(H00E,H00G)
2.c Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00U(H00U), C00V(H00V), C00X(H00X), C00Y(H00Y),
 C010(H010), C011(H011), C012(H012), C013(H013)
2.d Idealised Me refined as rotating group:
 C00Z(H00H,H00I,H00N), C014(H01A,H01B,H01C)
;
_shelx_res_checksum              84816
_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 2.993
_oxdiff_exptl_absorpt_empirical_full_min 0.289