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#$Date: 2023-07-05 12:18:16 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/16/7131690.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7131690
loop_
_publ_author_name
'Ye, Hao'
'Zhu, Xi-Wei'
'Pan, Yi-Yun'
'Sun, Jie'
'Sun, Fei'
'Wu, Xin-Xing'
_publ_section_title
;
 Highly regioselective and stereoselective cascade reductive cyclization
 of δ-ketoamide: practical access to oxa-bridged benzazepines.
;
_journal_issue                   49
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7587
_journal_page_last               7590
_journal_paper_doi               10.1039/d3cc01495a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_sum            'C19 H20 Cl N O'
_chemical_formula_weight         313.81
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-03-16 deposited with the CCDC.	2023-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                109.224(14)
_cell_angle_beta                 91.783(15)
_cell_angle_gamma                96.951(14)
_cell_formula_units_Z            2
_cell_length_a                   7.564(9)
_cell_length_b                   10.371(12)
_cell_length_c                   11.366(14)
_cell_measurement_reflns_used    3483
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.5975
_cell_measurement_theta_min      2.7205
_cell_volume                     833.3(17)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1891
_diffrn_reflns_av_unetI/netI     0.1226
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16878
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         3.198
_exptl_absorpt_coefficient_mu    0.231
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.355
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.355
_refine_ls_R_factor_all          0.2439
_refine_ls_R_factor_gt           0.1879
_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/[σ²(Fo²)+(0.1000P)²+1.2950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2712
_refine_ls_wR_factor_ref         0.2955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1895
_reflns_number_total             2920
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc01495a2.cif
_cod_data_source_block           20210322wuxx_0m_a
_cod_depositor_comments          'Adding full bibliography for 7131690.cif.'
_cod_database_code               7131690
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0927(8) 0.7864(6) 0.8952(5) 0.0334(15) Uani 1 1 d . . . . .
C2 C 0.9346(9) 0.8291(6) 0.8664(6) 0.0394(17) Uani 1 1 d . . . . .
H2 H 0.9351 0.9163 0.8601 0.047 Uiso 1 1 calc R U . . .
C3 C 0.7759(8) 0.7396(6) 0.8473(6) 0.0387(17) Uani 1 1 d . . . . .
H3 H 0.6694 0.7690 0.8307 0.046 Uiso 1 1 calc R U . . .
C4 C 0.7723(7) 0.6064(5) 0.8523(5) 0.0246(14) Uani 1 1 d . . . . .
C5 C 0.9335(8) 0.5667(6) 0.8806(5) 0.0355(16) Uani 1 1 d . . . . .
H5 H 0.9342 0.4786 0.8845 0.043 Uiso 1 1 calc R U . . .
C6 C 1.0936(8) 0.6559(6) 0.9032(6) 0.0376(17) Uani 1 1 d . . . . .
H6 H 1.1996 0.6284 0.9234 0.045 Uiso 1 1 calc R U . . .
C7 C 0.5956(8) 0.5114(6) 0.8313(5) 0.0314(15) Uani 1 1 d . . . . .
H7 H 0.5083 0.5631 0.8819 0.038 Uiso 1 1 calc R U . . .
C8 C 0.5184(8) 0.4527(6) 0.6931(5) 0.0336(15) Uani 1 1 d . . . . .
H8 H 0.5094 0.5303 0.6630 0.040 Uiso 1 1 calc R U . . .
C9 C 0.3267(8) 0.3758(7) 0.6878(6) 0.0455(18) Uani 1 1 d . . . . .
H9A H 0.2991 0.3034 0.6074 0.055 Uiso 1 1 calc R U . . .
H9B H 0.2404 0.4398 0.6971 0.055 Uiso 1 1 calc R U . . .
C10 C 0.3144(9) 0.3121(7) 0.7944(6) 0.0471(18) Uani 1 1 d . . . . .
H10 H 0.2891 0.3841 0.8704 0.057 Uiso 1 1 calc R U . . .
C11 C 0.5018(8) 0.2745(6) 0.8174(6) 0.0359(16) Uani 1 1 d . . . . .
H11 H 0.4901 0.2272 0.8791 0.043 Uiso 1 1 calc R U . . .
C12 C 0.1675(10) 0.1921(8) 0.7678(8) 0.066(2) Uani 1 1 d . . . . .
H12A H 0.0554 0.2207 0.7527 0.099 Uiso 1 1 calc R U . . .
H12B H 0.1621 0.1607 0.8383 0.099 Uiso 1 1 calc R U . . .
H12C H 0.1915 0.1185 0.6954 0.099 Uiso 1 1 calc R U . . .
C13 C 0.6033(12) 0.0448(7) 0.7123(8) 0.066(2) Uani 1 1 d . . . . .
H13A H 0.5743 -0.0238 0.6312 0.099 Uiso 1 1 calc R U . . .
H13B H 0.5298 0.0213 0.7716 0.099 Uiso 1 1 calc R U . . .
H13C H 0.7268 0.0487 0.7373 0.099 Uiso 1 1 calc R U . . .
C14 C 0.6645(8) 0.2304(6) 0.6207(5) 0.0366(16) Uani 1 1 d . . . . .
C15 C 0.7779(10) 0.1516(7) 0.5399(6) 0.052(2) Uani 1 1 d . . . . .
H15 H 0.7920 0.0650 0.5434 0.062 Uiso 1 1 calc R U . . .
C16 C 0.8702(10) 0.1996(8) 0.4544(7) 0.060(2) Uani 1 1 d . . . . .
H16 H 0.9436 0.1447 0.4017 0.072 Uiso 1 1 calc R U . . .
C17 C 0.8527(10) 0.3285(8) 0.4480(6) 0.053(2) Uani 1 1 d . . . . .
H17 H 0.9149 0.3616 0.3922 0.064 Uiso 1 1 calc R U . . .
C18 C 0.7402(9) 0.4070(7) 0.5267(6) 0.0416(17) Uani 1 1 d . . . . .
H18 H 0.7286 0.4938 0.5228 0.050 Uiso 1 1 calc R U . . .
C19 C 0.6428(8) 0.3611(6) 0.6122(5) 0.0325(15) Uani 1 1 d . . . . .
Cl1 Cl 1.2961(2) 0.89812(19) 0.92212(18) 0.0581(7) Uani 1 1 d . . . . .
N1 N 0.5713(8) 0.1795(5) 0.7072(5) 0.0449(15) Uani 1 1 d . . . . .
O1 O 0.6228(5) 0.3978(4) 0.8742(3) 0.0366(11) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.9(6) . . ?
C6 C1 Cl1 118.9(5) . . ?
C2 C1 Cl1 120.2(5) . . ?
C3 C2 C1 119.0(6) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 121.6(6) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 117.8(6) . . ?
C5 C4 C7 122.1(5) . . ?
C3 C4 C7 120.1(5) . . ?
C6 C5 C4 121.6(6) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C1 C6 C5 119.1(5) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
O1 C7 C4 108.3(4) . . ?
O1 C7 C8 108.9(5) . . ?
C4 C7 C8 114.0(5) . . ?
O1 C7 H7 108.5 . . ?
C4 C7 H7 108.5 . . ?
C8 C7 H7 108.5 . . ?
C19 C8 C7 110.5(5) . . ?
C19 C8 C9 113.0(5) . . ?
C7 C8 C9 108.5(5) . . ?
C19 C8 H8 108.2 . . ?
C7 C8 H8 108.2 . . ?
C9 C8 H8 108.2 . . ?
C8 C9 C10 109.8(5) . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C12 C10 C11 113.1(6) . . ?
C12 C10 C9 113.3(6) . . ?
C11 C10 C9 107.1(5) . . ?
C12 C10 H10 107.7 . . ?
C11 C10 H10 107.7 . . ?
C9 C10 H10 107.7 . . ?
O1 C11 N1 112.4(5) . . ?
O1 C11 C10 109.2(5) . . ?
N1 C11 C10 115.1(5) . . ?
O1 C11 H11 106.5 . . ?
N1 C11 H11 106.5 . . ?
C10 C11 H11 106.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 118.0(6) . . ?
C15 C14 N1 121.0(6) . . ?
C19 C14 N1 121.0(5) . . ?
C16 C15 C14 121.8(7) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C17 C16 C15 120.3(7) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 118.4(7) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C17 C18 C19 122.8(6) . . ?
C17 C18 H18 118.6 . . ?
C19 C18 H18 118.6 . . ?
C18 C19 C14 118.6(6) . . ?
C18 C19 C8 119.4(6) . . ?
C14 C19 C8 122.0(5) . . ?
C14 N1 C13 117.8(6) . . ?
C14 N1 C11 120.7(5) . . ?
C13 N1 C11 117.6(5) . . ?
C11 O1 C7 115.2(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.386(8) . ?
C1 C2 1.390(9) . ?
C1 Cl1 1.763(7) . ?
C2 C3 1.390(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.399(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(8) . ?
C4 C7 1.522(9) . ?
C5 C6 1.394(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.449(7) . ?
C7 C8 1.552(8) . ?
C7 H7 0.9800 . ?
C8 C19 1.526(9) . ?
C8 C9 1.557(9) . ?
C8 H8 0.9800 . ?
C9 C10 1.560(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C12 1.507(10) . ?
C10 C11 1.552(9) . ?
C10 H10 0.9800 . ?
C11 O1 1.423(7) . ?
C11 N1 1.473(8) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N1 1.465(8) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.404(9) . ?
C14 C19 1.419(9) . ?
C14 N1 1.427(8) . ?
C15 C16 1.399(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.387(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.406(9) . ?
C18 H18 0.9300 . ?
