Synthesis of benzoazepine derivatives via Rh(iii)-catalyzed inert C(sp<sup>2</sup>)-H functionalization and [4 + 3] annulation.
Xu, Yuanshuang; Zhang, Linghua; Liu, Mengyang; Zhang, Xiaopeng; Zhang, Xinying; Fan, Xuesen; Organic & biomolecular chemistry 17 (2019) 8706–8710; doi:10.1039/c9ob01830a

data_7157081
_publ_section_title
;
 Synthesis of benzoazepine derivatives via Rh(iii)-catalyzed inert
 C(sp<sup>2</sup>)-H functionalization and [4 + 3] annulation.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8706
_journal_page_last               8710
_journal_paper_doi               10.1039/c9ob01830a
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H17 F N2 O2'
_chemical_formula_sum            'C21 H17 F N2 O2'
_chemical_formula_weight         348.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-26
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_audit_update_record
;
2019-06-26 deposited with the CCDC.    2019-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7924(3)
_cell_length_b                   10.9272(3)
_cell_length_c                   18.0980(7)
_cell_measurement_reflns_used    2247
_cell_measurement_temperature    296.93(13)
_cell_measurement_theta_max      72.3240
_cell_measurement_theta_min      4.7240
_cell_volume                     1738.79(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.93(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6296
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.975
_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    -64.00  29.00   1.00    1.65    --  -40.77  44.00 -84.00   93
  2  \w    109.00 134.00   1.00    6.59    --  103.55  78.00  69.00   25
  3  \w    151.00 177.00   1.00    6.59    --  103.55  78.00  69.00   26
  4  \w     99.00 129.00   1.00    6.59    --  103.55 -44.00 124.00   30
  5  \w     98.00 161.00   1.00    6.59    --  103.55 122.00 141.00   63
  6  \w   -101.00 -61.00   1.00    1.65    --  -40.77-152.00-100.00   40
  7  \w     -6.00  43.00   1.00    1.65    --   40.77 -38.00  30.00   49
  8  \w    108.00 170.00   1.00    6.59    --  103.55 111.00 -60.00   62
  9  \w    136.00 168.00   1.00    6.59    --  103.55 111.00-180.00   32
 10  \w    101.00 177.00   1.00    6.59    --  103.55 111.00-120.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0896337000
_diffrn_orient_matrix_UB_12      -0.0254211000
_diffrn_orient_matrix_UB_13      0.0714996000
_diffrn_orient_matrix_UB_21      -0.0309742000
_diffrn_orient_matrix_UB_22      0.1379152000
_diffrn_orient_matrix_UB_23      0.0087029000
_diffrn_orient_matrix_UB_31      -0.1473827000
_diffrn_orient_matrix_UB_32      -0.0135960000
_diffrn_orient_matrix_UB_33      -0.0454274000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5171
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.436
_diffrn_reflns_theta_min         4.727
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.42a (Rigaku Oxford Diffraction, 2019)
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    1.331
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 924 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0431P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.576
_reflns_Friedel_fraction_full    0.813
_reflns_Friedel_fraction_max     0.762
_reflns_number_gt                2671
_reflns_number_total             3045
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01830a2.cif
_cod_data_source_block           3k
_cod_depositor_comments
'Adding full bibliography for 7157080--7157083.cif.'
_cod_database_code               7157081
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C1 H1 O1 F1'
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.861
_diffrn_oxdiff_digest_frames
;
01b4e1b6d4c14fd69fbb056d835ee32406000309db0
;
_diffrn_oxdiff_digest_hkl
;
012c32694eb0a1370e9c18db8116761dc2068a
;
_reflns_odcompleteness_completeness 99.72
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13B,H13A), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C5(H5), C6(H6), C7(H7), C10(H10), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 1.196
_oxdiff_exptl_absorpt_empirical_full_min 0.821