Deconstructive Functionalizations of Unstrained Carbon–Nitrogen Cleavage Enabled by Difluorocarbene
Su, Jianke; Ma, Xingxing; Ou, Zongliang; Song, Qiuling; ACS Central Science  (2020) –; doi:10.1021/acscentsci.0c00779

data_4517991
_publ_section_title
;
 Deconstructive Functionalizations of Unstrained Carbon--Nitrogen Cleavage
 Enabled by Difluorocarbene
;
_journal_name_full               'ACS Central Science'
_journal_paper_doi               10.1021/acscentsci.0c00779
_journal_year                    2020
_chemical_formula_moiety         'C14 H12 F N O'
_chemical_formula_sum            'C14 H12 F N O'
_chemical_formula_weight         229.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.399(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5597(14)
_cell_length_b                   9.5439(15)
_cell_length_c                   14.732(2)
_cell_measurement_reflns_used    1152
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9070
_cell_measurement_theta_min      3.8660
_cell_volume                     1160.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -25.00  30.00   1.00   12.50    --   15.34 -57.00  30.00   55
  2  \w     -6.00  22.00   1.00   12.50    --  -16.12 -99.00  60.00   28
  3  \w    -10.00  16.00   1.00   12.50    --  -16.12 -99.00 -30.00   26
  4  \w    -24.00  18.00   1.00   12.50    --  -16.12 -99.00 -90.00   42
  5  \w    -54.00 -29.00   1.00   12.50    --   15.34 -38.00   0.00   25
  6  \w    -83.00 -49.00   1.00   12.50    --  -16.12 -57.00   0.00   34
  7  \w     47.00  85.00   1.00   12.50    --   15.34 178.00 -30.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0047082000
_diffrn_orient_matrix_UB_12      -0.0059435000
_diffrn_orient_matrix_UB_13      0.0486066000
_diffrn_orient_matrix_UB_21      0.0689853000
_diffrn_orient_matrix_UB_22      0.0444418000
_diffrn_orient_matrix_UB_23      0.0107180000
_diffrn_orient_matrix_UB_31      -0.0509611000
_diffrn_orient_matrix_UB_32      0.0593977000
_diffrn_orient_matrix_UB_33      -0.0031617000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5052
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.576
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.851
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.851
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0499
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1509
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1321
_reflns_number_total             2037
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            oc0c00779_si_002.cif
_cod_data_source_block           exp_7188
_cod_database_code               4517991
_reflns_odcompleteness_completeness 99.48
_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 Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C),
 C00D(H00D), C00E(H00E), C00G(H00G)
2.b Idealised Me refined as rotating group:
 C00H(H00F,H00H,H00I)
;
_shelx_res_checksum              17198
_shelx_hkl_checksum              16907
_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 3.267
_oxdiff_exptl_absorpt_empirical_full_min 0.353