Three-step process for the synthesis of 10,11-dihydro-5H-dibenzo[b,f]azepin-10-ol derivatives
Sroor, Farid M.; Terme, Thierry; Vanelle, Patrice; Spitz, Cédric; RSC Advances 15 (2025) 6737–6741; doi:10.1039/D5RA00909J

data_7250073
_publ_section_title
;
 Three-step process for the synthesis of
 10,11-dihydro-5H-dibenzo[b,f]azepin-10-ol derivatives
;
_journal_issue                   9
_journal_name_full               'RSC Advances'
_journal_page_first              6737
_journal_page_last               6741
_journal_paper_doi               10.1039/D5RA00909J
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C15 H15 N O'
_chemical_formula_sum            'C15 H15 N O'
_chemical_formula_weight         225.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-27
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-17 deposited with the CCDC.	2025-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.848(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.33993(16)
_cell_length_b                   8.41329(17)
_cell_length_c                   19.6870(5)
_cell_measurement_reflns_used    5508
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      72.2920
_cell_measurement_theta_min      5.6960
_cell_volume                     1211.38(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3045
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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    -53.00  31.00   1.00    2.00    --  -40.79  54.00 123.00   84
  2  \w   -112.00 -14.00   1.00    2.00    --  -40.79 -54.00 -20.00   98
  3  \w     69.00 107.00   1.00    2.00    --   40.79  54.00 123.00   38
  4  \w     43.00 130.00   1.00    5.00    --  103.33 -54.00 -20.00   87
  5  \w     91.00 167.00   1.00    5.00    --  103.33  54.00 123.00   76
  6  \w     36.00  83.00   1.00    2.00    --   40.79-125.00 -60.00   47
  7  \w     29.00  93.00   1.00    2.00    --   40.79-125.00-120.00   64
  8  \w     14.00 113.00   1.00    2.00    --   40.79  57.00-120.00   99
  9  \w     42.00  70.00   1.00    2.00    --   40.79-125.00-180.00   28
 10  \w     63.00 146.00   1.00    5.00    --  103.33 178.00-120.00   83
 11  \w     79.00 106.00   1.00    5.00    --  103.33  45.00-120.00   27
 12  \w     94.00 121.00   1.00    5.00    --  103.33  61.00 -90.00   27
 13  \w     79.00 151.00   1.00    5.00    --  103.33  45.00 -90.00   72
 14  \w     74.00 100.00   1.00    5.00    --  103.33  61.00-120.00   26
 15  \w     76.00 114.00   1.00    5.00    --  103.33  61.00   0.00   38
 16  \w     78.00 104.00   1.00    5.00    --  103.33  45.00-150.00   26
 17  \w    146.00 173.00   1.00    5.00    --  103.33  45.00-150.00   27
 18  \w    105.00 134.00   1.00    5.00    --  103.33  77.00  30.00   29
 19  \w    135.00 176.00   1.00    5.00    --  103.33  77.00  30.00   41
 20  \w    113.00 165.00   1.00    5.00    --  103.33  61.00-180.00   52
 21  \w    122.00 175.00   1.00    5.00    --  103.33 111.00   0.00   53
 22  \w     75.00 100.00   1.00    5.00    --  103.33  61.00-180.00   25
 23  \w    132.00 159.00   1.00    5.00    --  103.33 111.00 -30.00   27
 24  \w    109.00 165.00   1.00    5.00    --  103.33  45.00-120.00   56
 25  \w     77.00 104.00   1.00    5.00    --  103.33  61.00-150.00   27
 26  \w     34.00 108.00   1.00    5.00    --  103.33-111.00   0.00   74
 27  \w     33.00  74.00   1.00    5.00    --  103.33-111.00-150.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0611301000
_diffrn_orient_matrix_UB_12      -0.0739050000
_diffrn_orient_matrix_UB_13      0.0659439000
_diffrn_orient_matrix_UB_21      0.1806462000
_diffrn_orient_matrix_UB_22      -0.0937568000
_diffrn_orient_matrix_UB_23      0.0095057000
_diffrn_orient_matrix_UB_31      0.0893744000
_diffrn_orient_matrix_UB_32      0.1389077000
_diffrn_orient_matrix_UB_33      0.0415587000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9632
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.426
_diffrn_reflns_theta_min         4.508
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2371
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0694P)^2^+0.2322P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1284
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2067
_reflns_number_total             2371
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra00909j2.cif
_cod_data_source_block           cs8029
_cod_database_code               7250073
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.899
_shelx_estimated_absorpt_t_min   0.888
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              13981
_shelx_hkl_checksum              32728
_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 1.397
_oxdiff_exptl_absorpt_empirical_full_min 0.572