An interrupted Corey-Chaykovsky reaction of designed azaarenium salts: synthesis of complex polycyclic spiro- and fused cyclopropanoids.
Singh, Bara; Ansari, Arshad J.; Malik, Nirmal; Ramasastry, S. S. V.; Chemical science 14 (2023) 6963–6969; doi:10.1039/d3sc01578e

data_1569273
_publ_section_title
;
 An interrupted Corey-Chaykovsky reaction of designed azaarenium salts:
 synthesis of complex polycyclic spiro- and fused cyclopropanoids.
;
_journal_issue                   25
_journal_name_full               'Chemical science'
_journal_page_first              6963
_journal_page_last               6969
_journal_paper_doi               10.1039/d3sc01578e
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C22 H19 N O'
_chemical_formula_sum            'C22 H19 N O'
_chemical_formula_weight         313.402
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-01-10 deposited with the CCDC.	2023-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.981(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2759(4)
_cell_length_b                   18.6849(8)
_cell_length_c                   11.6613(6)
_cell_measurement_reflns_used    3215
_cell_measurement_temperature    298
_cell_measurement_theta_max      32.0370
_cell_measurement_theta_min      3.3570
_cell_volume                     1724.62(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9898
_diffrn_measured_fraction_theta_max 0.8801
_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    -68.00 115.00   0.30   20.00    --   29.89  54.00 150.00  610
  2  \w     25.00  49.90   0.30   20.00    --   29.89  54.00  30.00   83
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0386740000
_diffrn_orient_matrix_UB_12      0.0264618000
_diffrn_orient_matrix_UB_13      -0.0267864000
_diffrn_orient_matrix_UB_21      -0.0363937000
_diffrn_orient_matrix_UB_22      0.0272407000
_diffrn_orient_matrix_UB_23      0.0269018000
_diffrn_orient_matrix_UB_31      0.0720870000
_diffrn_orient_matrix_UB_32      -0.0004486000
_diffrn_orient_matrix_UB_33      0.0510626000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.9898
_diffrn_reflns_Laue_measured_fraction_max 0.8801
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8796
_diffrn_reflns_point_group_measured_fraction_full 0.9898
_diffrn_reflns_point_group_measured_fraction_max 0.8801
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         32.67
_diffrn_reflns_theta_min         3.37
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       prism
_exptl_crystal_F_000             664.278
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.2703
_refine_diff_density_min         -0.1915
_refine_diff_density_rms         0.0422
_refine_ls_d_res_high            0.6584
_refine_ls_d_res_low             6.0391
_refine_ls_goodness_of_fit_ref   1.2112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     218
_refine_ls_number_reflns         5576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.2112
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.0077
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1745
_refine_ls_wR_factor_ref         0.1994
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              28
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3996
_reflns_number_total             5576
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3sc01578e2.cif
_cod_data_source_block           AJANONPOLAR
_cod_depositor_comments
'Adding full bibliography for 1569272--1569274.cif.'
_cod_database_code               1569273
_reflns_odcompleteness_completeness 98.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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.a Ternary CH refined with riding coordinates:
 C00C(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00a,H00b)
2.c Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00J(H00J), C00I(H00I), C00D(H00D), C007(H007), C00H(H00H),
 C00E(H00E), C002(H002), C00L(H00L), C00N(H00N), C00M(H00M), C00K(H00K),
 C00F(H00F)
2.d Idealised Me refined as rotating group:
 C00O(H00o,H00p,H00q)
;
_olex2_submission_original_sample_id 'AJA NON POLAR'
_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 1.420
_oxdiff_exptl_absorpt_empirical_full_min 0.855