Asymmetric transfer hydrogenation of seven membered tricyclic ketones: N-substituted dibenzo[b,e]azepine-6,11-dione driven by nonclassical CH/O interactions
Vyas, Vijyesh K.; Bhanage, Bhalchandra M.; Organic Chemistry Frontiers 3 (2016) 614–; doi:10.1039/C6QO00036C

data_1553430
_publ_section_title
;
 Asymmetric transfer hydrogenation of seven membered tricyclic ketones:
 N-substituted dibenzo[b,e]azepine-6,11-dione driven by nonclassical CH/O
 interactions
;
_journal_issue                   5
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              614
_journal_paper_doi               10.1039/C6QO00036C
_journal_volume                  3
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H16 Cl N O2'
_chemical_formula_sum            'C17 H16 Cl N O2'
_chemical_formula_weight         301.76
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-14
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-12-23 deposited with the CCDC.
2016-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1449(2)
_cell_length_b                   10.8999(4)
_cell_length_c                   16.4545(6)
_cell_measurement_reflns_used    2749
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.3240
_cell_measurement_theta_min      4.8410
_cell_volume                     1460.81(8)
_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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.1600
_diffrn_detector_type            Titan
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_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      4.00  81.00   1.00    1.00    --   43.54-126.00 -60.00   77
  2  \w     35.00 116.00   1.00    3.00    --  102.90-126.00   0.00   81
  3  \w     20.00 107.00   1.00    3.00    --  102.90 -95.00-180.00   87
  4  \w     71.00 157.00   1.00    3.00    --  102.90  15.00 -60.00   86
  5  \w    118.00 144.00   1.00    3.00    --  102.90 126.00 -60.00   26
  6  \w     75.00 153.00   1.00    3.00    --  102.90  77.00  60.00   78
  7  \w   -103.00 -11.00   1.00    1.00    --  -43.54 -19.00  60.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Titan'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1127639000
_diffrn_orient_matrix_UB_12      -0.0243483000
_diffrn_orient_matrix_UB_13      -0.0733811000
_diffrn_orient_matrix_UB_21      0.0656066000
_diffrn_orient_matrix_UB_22      -0.1167018000
_diffrn_orient_matrix_UB_23      0.0417285000
_diffrn_orient_matrix_UB_31      -0.1370599000
_diffrn_orient_matrix_UB_32      -0.0758890000
_diffrn_orient_matrix_UB_33      -0.0404289000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5196
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.871
_diffrn_reflns_theta_min         4.867
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.344
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.522
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.372
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.628
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 750 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_coef       0.0138(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0500
_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^)+(0.0525P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1301
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                2382
_reflns_number_total             2829
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00036c2.cif
_cod_data_source_block           ict1_1
_cod_original_cell_volume        1460.82(8)
_cod_database_code               1553430
_chemical_oxdiff_formula         'C17 H16 Cl N O2'
_reflns_odcompleteness_completeness 99.94
_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:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C17(H17), C5(H5), C14(H14), C16(H16), C15(H15), C7(H7), C6(H6)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              28246
_shelx_hkl_checksum              59898
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-12-11
_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 2.373
_oxdiff_exptl_absorpt_empirical_full_min 0.310