One-pot synthesis of multisubstituted spirocyclopropanes mediated by α-picoline
Ma, Huifang; Liang, Jie; Ablajan, Keyume; New Journal of Chemistry 46 (2022) 19857–19862; doi:10.1039/D2NJ04102B

data_7061965
_publ_section_title
;
 One-pot synthesis of multisubstituted spirocyclopropanes mediated by
 \a-picoline
;
_journal_issue                   41
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19857
_journal_page_last               19862
_journal_paper_doi               10.1039/D2NJ04102B
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C25 H18 Cl N3 O4'
_chemical_formula_sum            'C25 H18 Cl N3 O4'
_chemical_formula_weight         459.87
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc1z0tqj
_audit_creation_date             2017-08-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_audit_update_record
;
2018-01-19 deposited with the CCDC.	2022-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                95.201(4)
_cell_angle_beta                 95.657(4)
_cell_angle_gamma                92.809(4)
_cell_formula_units_Z            2
_cell_length_a                   7.5127(4)
_cell_length_b                   9.5403(5)
_cell_length_c                   14.8625(7)
_cell_measurement_reflns_used    3396
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.9420
_cell_measurement_theta_min      4.1970
_cell_volume                     1053.89(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.835
_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    -34.00  56.00   1.00    2.00    --  -11.59  57.00   0.00   90
  2  \w    -19.00   6.00   1.00    2.00    --   11.74 -99.00 150.00   25
  3  \w    -77.00  17.00   1.00    2.00    --  -11.59 -77.00  90.00   94
  4  \w    -82.00  16.00   1.00    2.00    --  -11.59 -57.00-150.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0731521000
_diffrn_orient_matrix_UB_12      -0.0437356000
_diffrn_orient_matrix_UB_13      0.0100023000
_diffrn_orient_matrix_UB_21      0.0265443000
_diffrn_orient_matrix_UB_22      0.0156035000
_diffrn_orient_matrix_UB_23      0.0471237000
_diffrn_orient_matrix_UB_31      -0.0545554000
_diffrn_orient_matrix_UB_32      0.0586194000
_diffrn_orient_matrix_UB_33      0.0008243000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8667
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.572
_diffrn_reflns_theta_min         3.571
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0360P)^2^+0.2826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1024
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3921
_reflns_number_total             4943
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj04102b2.cif
_cod_data_source_block           exp_809
_cod_depositor_comments
'Adding full bibliography for 7061965--7061966.cif.'
_cod_database_code               7061965
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.961
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C4(H4), C3(H3), C19(H19), C13(H13), C22(H22), C5(H5), C2(H2),
 C16(H16), C15(H15), C21(H21), C20(H20), C14(H14)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.232
_oxdiff_exptl_absorpt_empirical_full_min 0.817