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_7061966
_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 H17 Br2 N O3'
_chemical_formula_sum            'C25 H17 Br2 N O3'
_chemical_formula_weight         539.21
_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     dual
_audit_creation_date             2018-10-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-01 deposited with the CCDC.	2022-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                78.549(5)
_cell_angle_beta                 83.673(5)
_cell_angle_gamma                76.958(5)
_cell_formula_units_Z            2
_cell_length_a                   7.0127(4)
_cell_length_b                   10.5218(6)
_cell_length_c                   14.9131(8)
_cell_measurement_reflns_used    5486
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.1880
_cell_measurement_theta_min      2.2420
_cell_volume                     1048.19(11)
_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 0.999
_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    -60.00  40.00   1.00    1.50    --   11.74 -57.00   0.00  100
  2  \w    -21.00  88.00   1.00    1.50    --   11.74  77.00 -90.00  109
  3  \w    -16.00  85.00   1.00    1.50    --   11.74  57.00 150.00  101
  4  \w     34.00  99.00   1.00    1.50    --   11.74-178.00   0.00   65
  5  \w    -16.00  25.00   1.00    1.50    --   11.74  57.00  30.00   41
  6  \w    -20.00  53.00   1.00    1.50    --   11.74 -99.00-180.00   73
;
_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      -0.0820459000
_diffrn_orient_matrix_UB_12      -0.0045901000
_diffrn_orient_matrix_UB_13      0.0319265000
_diffrn_orient_matrix_UB_21      0.0210836000
_diffrn_orient_matrix_UB_22      0.0501874000
_diffrn_orient_matrix_UB_23      0.0204712000
_diffrn_orient_matrix_UB_31      -0.0604483000
_diffrn_orient_matrix_UB_32      0.0490672000
_diffrn_orient_matrix_UB_33      -0.0304581000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11956
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         2.240
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.895
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48416
_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            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.088
_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     281
_refine_ls_number_reflns         3711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0306P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0705
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3270
_reflns_number_total             3711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj04102b2.cif
_cod_data_source_block           mhf
_cod_depositor_comments
'Adding full bibliography for 7061965--7061966.cif.'
_cod_database_code               7061966
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.95
_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:
 C8(H8), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C25(H25), C15(H15), C6(H6), C24(H24), C21(H21), C5(H5),
 C16(H16), C22(H22), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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 1.576
_oxdiff_exptl_absorpt_empirical_full_min 0.784