Cascade C-H Functionalization/Amidation Reaction for Synthesis of Azepinone Derivatives.
Bai, Peng; Huang, Xing-Fen; Xu, Guo-Dong; Huang, Zhi-Zhen; Organic letters 18 (2016) 3058–3061; doi:10.1021/acs.orglett.6b01140

data_1543808
_publ_section_title
;
 Cascade C-H Functionalization/Amidation Reaction for Synthesis of
 Azepinone Derivatives.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3058
_journal_page_last               3061
_journal_paper_doi               10.1021/acs.orglett.6b01140
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C17 H14 Cl N O3, C H Cl3'
_chemical_formula_sum            'C18 H15 Cl4 N O3'
_chemical_formula_weight         435.11
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                68.353(8)
_cell_angle_beta                 88.982(7)
_cell_angle_gamma                82.872(7)
_cell_formula_units_Z            2
_cell_length_a                   7.9118(6)
_cell_length_b                   11.5272(10)
_cell_length_c                   11.8921(10)
_cell_measurement_reflns_used    1505
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3906
_cell_measurement_theta_min      3.4098
_cell_volume                     999.83(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0604963000
_diffrn_orient_matrix_UB_12      -0.0419541000
_diffrn_orient_matrix_UB_13      0.0268797000
_diffrn_orient_matrix_UB_21      0.0659285000
_diffrn_orient_matrix_UB_22      -0.0450654000
_diffrn_orient_matrix_UB_23      0.0362180000
_diffrn_orient_matrix_UB_31      -0.0128136000
_diffrn_orient_matrix_UB_32      0.0257467000
_diffrn_orient_matrix_UB_33      0.0456880000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6296
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.42
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0671P)^2^+0.2684P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1494
_reflns_number_gt                2522
_reflns_number_total             3642
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b01140_si_002.cif
_cod_data_source_block           160317_3e_bai1601072
_cod_original_cell_volume        999.82(14)
_cod_database_code               1543808
_chemical_oxdiff_formula         'c10 h10 n2 o8 Cl1'
_reflns_odcompleteness_completeness 99.54
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(Cl6A)=Sof(Cl5A)=Sof(C18A)=Sof(H18A)=Sof(Cl7A)=1-FVAR(1)
 Sof(Cl5)=Sof(Cl7)=Sof(Cl6)=Sof(C18)=Sof(H18)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C13(H13), C18(H18), C18A(H18A)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C8(H8), C5(H5), C4(H4), C9(H9), C2(H2), C3(H3)
3.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;