Lewis Acid-mediated Formation of 1,3-Disubstituted Spiro[cyclopropane-1,2'-indanes]: The Activating Effect of the Cyclopropane Walsh Orbital.
Alajarin, Mateo; Ballester, Francisco-Jose; Vivancos, Juan-Antonio; Orenes, Raul-Angel; Vidal, Ángel; Sanchez-Andrada, Pilar; Marin-Luna, Marta; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00090

data_4037987
_publ_section_title
;
 Lewis Acid-mediated Formation of 1,3-Disubstituted
 Spiro[cyclopropane-1,2'-indanes]: The Activating Effect of the
 Cyclopropane Walsh Orbital.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00090
_journal_year                    2020
_chemical_formula_sum            'C23 H20 Br2 N2'
_chemical_formula_weight         484.23
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.915(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0269(5)
_cell_length_b                   7.4380(6)
_cell_length_c                   42.688(4)
_cell_measurement_reflns_used    9665
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.58
_cell_measurement_theta_min      2.78
_cell_volume                     1913.4(3)
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2011)'
_computing_data_collection       'APEX 2013.2 (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2011)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'omega + phi scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'high brilliance microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       61
_diffrn_reflns_limit_l_min       -61
_diffrn_reflns_number            111217
_diffrn_reflns_theta_full        30.99
_diffrn_reflns_theta_max         30.99
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    4.247
_exptl_absorpt_correction_T_max  0.9199
_exptl_absorpt_correction_T_min  0.6761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         4.099
_refine_diff_density_min         -3.490
_refine_diff_density_rms         0.315
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.311
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         6082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.311
_refine_ls_R_factor_all          0.1464
_refine_ls_R_factor_gt           0.1358
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0840P)^2^+68.1020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3388
_refine_ls_wR_factor_ref         0.3436
_reflns_number_gt                5443
_reflns_number_total             6082
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00090_si_001.cif
_cod_data_source_block           fjbh_0mspyo_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037987