Cu-catalyzed one-pot synthesis of fused oxazepinone derivatives via sp2 C–H and O–H cross-dehydrogenative coupling
Zhang, Zeyuan; Dai, Zhen; Ma, Xinkun; Liu, Yihan; Ma, Xiaojun; Li, Wanli; Ma, Chen; Organic Chemistry Frontiers 3 (2016) 799–; doi:10.1039/C6QO00040A

data_1553433
_publ_section_title
;
 Cu-catalyzed one-pot synthesis of fused oxazepinone derivatives via sp2
 C--H and O--H cross-dehydrogenative coupling
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              799
_journal_paper_doi               10.1039/C6QO00040A
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C21 H12 Cl N3 O2'
_chemical_formula_sum            'C21 H12 Cl N3 O2'
_chemical_formula_weight         373.79
_chemical_name_common            3k
_chemical_name_systematic        3k
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-09-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-01-22 deposited with the CCDC.
2016-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                101.767(2)
_cell_angle_beta                 96.018(2)
_cell_angle_gamma                106.7307(18)
_cell_formula_units_Z            2
_cell_length_a                   7.1470(16)
_cell_length_b                   7.9449(18)
_cell_length_c                   16.405(4)
_cell_measurement_reflns_used    3273
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.550
_cell_measurement_theta_min      2.576
_cell_volume                     859.9(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8620
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.573
_exptl_absorpt_coefficient_mu    0.244
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0422
_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^)+(0.1000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1550
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2419
_reflns_number_total             3034
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00040a2.cif
_cod_data_source_block           p
_cod_original_cell_volume        860.0(3)
_cod_database_code               1553433
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C18(H18), C19(H19), C21(H21)
;
_shelx_res_checksum              77308
_shelx_hkl_checksum              89937
_olex2_submission_special_instructions 'No special instructions were received'