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_7157082
_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_formula_moiety         'C21 H16 N2 O'
_chemical_formula_sum            'C21 H16 N2 O'
_chemical_formula_weight         312.36
_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     direct
_audit_creation_date             2019-04-09
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-25 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            8
_cell_length_a                   11.2543(4)
_cell_length_b                   11.6498(3)
_cell_length_c                   23.6897(7)
_cell_measurement_reflns_used    4687
_cell_measurement_temperature    295.01(13)
_cell_measurement_theta_max      26.6240
_cell_measurement_theta_min      3.8960
_cell_volume                     3105.96(16)
_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      295.01(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6296
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.858
_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     23.00  49.00   1.00   17.50    --   10.83-148.00 171.00   26
  2  \w    -56.00  23.00   1.00   17.50    --   10.83 -56.00-151.00   79
  3  \w     -8.00  28.00   1.00   17.50    --   10.83 -99.00 150.00   36
  4  \w    -20.00  29.00   1.00   17.50    --  -11.77 -99.00 -90.00   49
;
_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      -0.0153447000
_diffrn_orient_matrix_UB_12      -0.0072304000
_diffrn_orient_matrix_UB_13      0.0288260000
_diffrn_orient_matrix_UB_21      0.0445921000
_diffrn_orient_matrix_UB_22      0.0399922000
_diffrn_orient_matrix_UB_23      0.0077982000
_diffrn_orient_matrix_UB_31      -0.0418175000
_diffrn_orient_matrix_UB_32      0.0453066000
_diffrn_orient_matrix_UB_33      -0.0022915000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            14916
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.677
_diffrn_reflns_theta_min         3.498
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33852
_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    yellow
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0501P)^2^+0.8864P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1336
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2603
_reflns_number_total             3768
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01830a2.cif
_cod_data_source_block           5
_cod_depositor_comments
'Adding full bibliography for 7157080--7157083.cif.'
_cod_original_cell_volume        3105.97(16)
_cod_database_code               7157082
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.984
_diffrn_oxdiff_digest_frames
;
01fd981e54672e879db198d13c57a8b8b900027d7c3
;
_diffrn_oxdiff_digest_hkl
;
0129cff6298eae9eacbd4c4381bd5635f36a22
;
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C20(H20), C21(H21)
;
_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 1.718
_oxdiff_exptl_absorpt_empirical_full_min 0.668