Intramolecular nucleophilic addition of carbanions generated from N-benzylamides to cyclopropenes.
Maslivetc, Vladimir; Barrett, Colby; Aksenov, Nicolai A.; Rubina, Marina; Rubin, Michael; Organic & biomolecular chemistry 16 (2018) 285–294; doi:10.1039/c7ob02068f

data_7156025
_publ_section_title
;
 Intramolecular nucleophilic addition of carbanions generated from
 N-benzylamides to cyclopropenes.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              285
_journal_page_last               294
_journal_paper_doi               10.1039/c7ob02068f
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C13 H14 F N O'
_chemical_formula_sum            'C13 H14 F N O'
_chemical_formula_weight         219.25
_chemical_name_systematic
4-(4-fluorophenyl)-1,3-dimethyl-3-azabicyclo[3.1.0]hexan-2-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-09-18 deposited with the CCDC.
2017-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.0397(5)
_cell_length_b                   10.6042(3)
_cell_length_c                   19.2081(9)
_cell_measurement_reflns_used    6275
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      75.7990
_cell_measurement_theta_min      4.5850
_cell_volume                     2248.64(16)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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    -79.00  36.00   1.00   10.00    --  -41.54  19.00 -30.00  115
  2  \w      6.00  56.00   1.00   10.00    --   41.54 -99.00  90.00   50
  3  \w     33.00  82.00   1.00   10.00    --   41.54 -99.00-120.00   49
  4  \w     29.00  98.00   1.00   45.00    --  107.59 -95.00 -60.00   69
  5  \w     49.00  91.00   1.00   45.00    --  107.59 -30.00 -90.00   42
  6  \w     35.00 110.00   1.00   55.00    --  107.59 -95.00  60.00   75
  7  \w     44.00  97.00   1.00   55.00    --  107.59 -45.00 -90.00   53
  8  \w     35.00  78.00   1.00   53.00    --  107.59 -30.00-120.00   43
  9  \w     76.00 106.00   1.00   53.00    --  107.59 -95.00-150.00   30
 10  \w     94.00 166.00   1.00   53.00    --  107.59 125.00   0.00   72
 11  \w    138.00 178.00   1.00   53.00    --  107.59  30.00  60.00   40
 12  \w     80.00 123.00   1.00   53.00    --  107.59  30.00  60.00   43
 13  \w    153.00 178.00   1.00   53.00    --  107.59  30.00 -90.00   25
 14  \w     49.00 114.00   1.00   51.80    --  112.00-111.00 120.00   65
 15  \w     50.00  76.00   1.00   51.80    --  112.00 -61.00  90.00   26
 16  \w    107.00 134.00   1.00   51.80    --  112.00 -61.00  90.00   27
 17  \w     47.00  73.00   1.00   51.80    --  112.00-145.00 -78.00   26
 18  \w    107.00 132.00   1.00   51.80    --  112.00-145.00 -78.00   25
 19  \w    132.00 158.00   1.00   51.80    --  112.00  45.00 -30.00   26
 20  \w   -114.00 -14.00   1.00   10.00    --  -42.35 -57.00 -30.00  100
 21  \w   -114.00 -51.00   1.00   10.00    --  -42.35 -57.00 120.00   63
 22  \w   -118.00 -10.00   1.00   10.00    --  -42.35 -77.00-120.00  108
 23  \w     49.00  74.00   1.00   51.80    --  112.00 -30.00-180.00   25
 24  \w     40.00  66.00   1.00   51.80    --  112.00-111.00  90.00   26
 25  \w     91.00 116.00   1.00   51.80    --  112.00-111.00  90.00   25
 26  \w     82.00 108.00   1.00   51.80    --  112.00-111.00 -60.00   26
 27  \w    120.00 156.00   1.00   51.80    --  112.00  45.00-180.00   36
 28  \w     65.00  92.00   1.00   51.80    --  112.00 -95.00 -30.00   27
;
_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      0.0846967000
_diffrn_orient_matrix_UB_12      0.0050171000
_diffrn_orient_matrix_UB_13      0.0636431000
_diffrn_orient_matrix_UB_21      -0.1105169000
_diffrn_orient_matrix_UB_22      -0.0094838000
_diffrn_orient_matrix_UB_23      0.0487721000
_diffrn_orient_matrix_UB_31      0.0099795000
_diffrn_orient_matrix_UB_32      -0.1448698000
_diffrn_orient_matrix_UB_33      -0.0009605000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15534
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.092
_diffrn_reflns_theta_min         4.604
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_recrystallization_method 'recrystallized From EtOAc'
_exptl_crystal_size_max          0.393
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0652
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1077P)^2^+0.8282P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1715
_refine_ls_wR_factor_ref         0.1812
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1959
_reflns_number_total             2317
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02068f2.cif
_cod_data_source_block           anna_01092017_cl_f2631_23
_cod_depositor_comments          'Adding full bibliography for 7156025.cif.'
_cod_database_code               7156025
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C13H14FNO
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C007(H007), C00A(H00A)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00G,H00H)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00C(H00C), C00E(H00F)
2.d Idealised Me refined as rotating group:
 C00D(H00B,H00D,H00E), C00G(H00I,H00J,H00K)
;
_shelx_res_checksum              76649
_olex2_date_sample_data_collection 2017-09-06
_olex2_exptl_crystal_mounting_method
'Mounted by acrylic glue on the glass stick'
_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 2.825
_oxdiff_exptl_absorpt_empirical_full_min 0.460