Enantioselective formation of cyclopropane spiroindenes from benzofulvenes by phase transfer catalysis.
Donslund, Bjarke S.; Jessen, Nicolaj Inunnguaq; Jakobsen, Joakim Bøgelund; Monleón, Alicia; Nielsen, Rune Pagh; Jørgensen, Karl Anker; Chemical communications (Cambridge, England) 52 (2016) 12474–12477; doi:10.1039/c6cc07170h

data_7125156
_publ_section_title
;
 Enantioselective formation of cyclopropane spiroindenes from
 benzofulvenes by phase transfer catalysis.
;
_journal_issue                   84
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12474
_journal_page_last               12477
_journal_paper_doi               10.1039/c6cc07170h
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H18 Br N O4'
_chemical_formula_sum            'C19 H18 Br N O4'
_chemical_formula_weight         404.26
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_symmetry_Int_Tables_number      144
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-08-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-08-12 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   15.6261(3)
_cell_length_b                   15.6261(3)
_cell_length_c                   6.58142(14)
_cell_measurement_reflns_used    11583
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      27.8320
_cell_measurement_theta_min      2.9780
_cell_volume                     1391.72(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.941
_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  99.00   1.00   23.87    --   10.84-178.00-150.00   65
  2  \w    -16.00  87.00   1.00   23.87    --   10.84  38.00-180.00  103
  3  \w    -35.00  92.00   1.00   23.87    --   10.84  19.00   0.00  127
  4  \w    -20.00  41.00   1.00   23.87    --   10.84 -99.00-120.00   61
  5  \w    -36.00  10.00   1.00   23.87    --   10.84 109.00 -89.00   46
  6  \w    -20.00  53.00   1.00   23.87    --   10.84 -99.00   0.00   73
  7  \w    -20.00  30.00   1.00   23.87    --  -11.86 -99.00 -30.00   50
  8  \w    -41.00  62.00   1.00   23.87    --  -11.86  57.00  30.00  103
  9  \w    -38.00  64.00   1.00   23.87    --  -11.86  38.00-120.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0268096000
_diffrn_orient_matrix_UB_12      0.0465809000
_diffrn_orient_matrix_UB_13      0.0487373000
_diffrn_orient_matrix_UB_21      0.0448663000
_diffrn_orient_matrix_UB_22      0.0007717000
_diffrn_orient_matrix_UB_23      -0.0211800000
_diffrn_orient_matrix_UB_31      0.0037533000
_diffrn_orient_matrix_UB_32      0.0240215000
_diffrn_orient_matrix_UB_33      -0.0937981000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            28798
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.480
_diffrn_reflns_theta_min         2.607
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.237
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       needle
_exptl_crystal_F_000             618
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.4506
_refine_diff_density_min         -0.2999
_refine_diff_density_rms         0.0778
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.011(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4732
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0292
_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^)+(0.0155P)^2^+0.5230P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0491
_refine_ls_wR_factor_ref         0.0517
_reflns_Friedel_coverage         0.886
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.886
_reflns_limit_h_max              17
_reflns_limit_h_min              -17
_reflns_limit_k_max              18
_reflns_limit_k_min              -18
_reflns_limit_l_max              9
_reflns_limit_l_min              -8
_reflns_number_gt                4298
_reflns_number_total             4732
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6cc07170h2.cif
_cod_data_source_block           2016_08_04
_cod_original_sg_symbol_Hall     ' P 31'
_cod_database_code               7125156
_chemical_oxdiff_formula         C19H18NO4Br
_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:
 C006(H006), C00G(H00K)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00D), C00C(H00E), C00D(H00F), C00F(H00J)
2.c Idealised Me refined as rotating group:
 C008(H00A,H00B,H00C), C00E(H00G,H00H,H00I), C00N(H00L,H00M,H00N), C00P(H00O,
 H00P,H00Q)
;
_shelx_shelxl_version_number     2014/7
_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 1.433
_oxdiff_exptl_absorpt_empirical_full_min 0.742