#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:39:43 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296699 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160115.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_7160115
loop_
_publ_author_name
'Suresh, Sundaram'
'Palla, Sowndarya'
'Chung, Dai-Ru'
'Chien, Hung-Sheng'
'Du, Bo-Xun'
'Shinde, Jivan'
'Kavala, Veerababurao'
'Yao, Ching-Fa'
_publ_section_title
;
 Catalyst-free reactions of anilines with β-chloroenones: synthesis
 of α-chloroenaminones and 1,4-benzodiazepines.
;
_journal_issue                   45
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8857
_journal_page_last               8868
_journal_paper_doi               10.1039/d4ob00954a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C18 H18 Cl N O'
_chemical_formula_sum            'C18 H18 Cl N O'
_chemical_formula_weight         299.78
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2024-07-15 deposited with the CCDC.	2024-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.434(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9614(6)
_cell_length_b                   15.4727(9)
_cell_length_c                   11.3672(7)
_cell_measurement_reflns_used    4682
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.09
_cell_measurement_theta_min      2.36
_cell_volume                     1652.20(17)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0954
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            34591
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_correction_T_min  0.8880
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0538P)²+1.2015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1516
_reflns_number_gt                2321
_reflns_number_total             2917
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4ob00954a2.cif
_cod_data_source_block           d25152
_cod_depositor_comments
'Adding full bibliography for 7160113--7160115.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7160115
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7205(3) 0.30885(16) 0.5493(2) 0.0381(6) Uani 1 1 d . . .
C2 C 0.8520(3) 0.30164(17) 0.6519(2) 0.0444(7) Uani 1 1 d . . .
C3 C 0.9277(3) 0.38251(17) 0.7097(2) 0.0381(6) Uani 1 1 d . . .
C4 C 0.8590(3) 0.44540(17) 0.7549(3) 0.0445(7) Uani 1 1 d . . .
H4 H 0.7607 0.4394 0.7440 0.053 Uiso 1 1 calc R . .
C5 C 0.9330(4) 0.5167(2) 0.8158(3) 0.0624(9) Uani 1 1 d . . .
H5 H 0.8859 0.5593 0.8479 0.075 Uiso 1 1 calc R . .
C6 C 1.0738(4) 0.5262(2) 0.8300(3) 0.0738(11) Uani 1 1 d . . .
H6 H 1.1244 0.5755 0.8719 0.089 Uiso 1 1 calc R . .
C7 C 1.1423(4) 0.4650(3) 0.7840(4) 0.0736(11) Uani 1 1 d . . .
H7 H 1.2398 0.4725 0.7928 0.088 Uiso 1 1 calc R . .
C8 C 1.0706(3) 0.3926(2) 0.7252(3) 0.0562(8) Uani 1 1 d . . .
H8 H 1.1192 0.3497 0.6952 0.067 Uiso 1 1 calc R . .
C9 C 0.6803(2) 0.38181(15) 0.4814(2) 0.0330(5) Uani 1 1 d . . .
H9 H 0.7360 0.4319 0.5124 0.040 Uiso 1 1 calc R . .
C10 C 0.5352(2) 0.47120(15) 0.3113(2) 0.0309(5) Uani 1 1 d . . .
C11 C 0.4675(3) 0.47195(17) 0.1837(2) 0.0371(6) Uani 1 1 d . . .
H11 H 0.4410 0.4191 0.1396 0.044 Uiso 1 1 calc R . .
C12 C 0.4383(3) 0.54977(18) 0.1199(3) 0.0451(7) Uani 1 1 d . . .
H12 H 0.3920 0.5492 0.0321 0.054 Uiso 1 1 calc R . .
C13 C 0.4745(3) 0.62805(18) 0.1804(3) 0.0474(7) Uani 1 1 d . . .
C14 C 0.4426(4) 0.7129(2) 0.1071(4) 0.0738(11) Uani 1 1 d . . .
H14 H 0.4295 0.6950 0.0195 0.089 Uiso 1 1 calc R . .
C15 C 0.3085(5) 0.7495(3) 0.0995(6) 0.1222(15) Uani 1 1 d . . .
H15A H 0.2940 0.8033 0.0513 0.183 Uiso 1 1 calc R . .
H15B H 0.3073 0.7618 0.1837 0.183 Uiso 1 1 calc R . .
H15C H 0.2323 0.7086 0.0582 0.183 Uiso 1 1 calc R . .
C16 C 0.5641(5) 0.7713(3) 0.1387(6) 0.1222(15) Uani 1 1 d . . .
H16A H 0.5381 0.8237 0.0877 0.183 Uiso 1 1 calc R . .
H16B H 0.6440 0.7427 0.1226 0.183 Uiso 1 1 calc R . .
H16C H 0.5918 0.7869 0.2272 0.183 Uiso 1 1 calc R . .
C17 C 0.5382(3) 0.62625(17) 0.3092(3) 0.0452(7) Uani 1 1 d . . .
H17 H 0.5619 0.6792 0.3535 0.054 Uiso 1 1 calc R . .
C18 C 0.5679(3) 0.54920(16) 0.3747(2) 0.0369(6) Uani 1 1 d . . .
H18 H 0.6107 0.5497 0.4629 0.044 Uiso 1 1 calc R . .
Cl1 Cl 0.62237(10) 0.21485(4) 0.49960(7) 0.0620(3) Uani 1 1 d . . .
N1 N 0.5705(2) 0.39128(13) 0.37514(18) 0.0348(5) Uani 1 1 d . . .
H1 H 0.5179 0.3458 0.3435 0.042 Uiso 1 1 calc R . .
O1 O 0.9035(3) 0.23089(13) 0.6924(2) 0.0749(8) 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'
Cl Cl 0.1484 0.1585 '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'
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
C9 C1 C2 123.0(2) . . ?
C9 C1 Cl1 119.10(19) . . ?
C2 C1 Cl1 117.38(19) . . ?
O1 C2 C1 121.7(3) . . ?
O1 C2 C3 119.5(2) . . ?
C1 C2 C3 118.8(2) . . ?
C8 C3 C4 119.2(3) . . ?
C8 C3 C2 119.9(3) . . ?
C4 C3 C2 120.8(2) . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C3 119.9(3) . . ?
C7 C8 H8 120.0 . . ?
C3 C8 H8 120.0 . . ?
N1 C9 C1 127.1(2) . . ?
N1 C9 H9 116.4 . . ?
C1 C9 H9 116.4 . . ?
C11 C10 C18 119.1(2) . . ?
C11 C10 N1 119.7(2) . . ?
C18 C10 N1 121.2(2) . . ?
C10 C11 C12 120.1(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 121.8(2) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C17 117.4(2) . . ?
C12 C13 C14 120.6(3) . . ?
C17 C13 C14 122.0(3) . . ?
C15 C14 C16 116.9(4) . . ?
C15 C14 C13 113.3(3) . . ?
C16 C14 C13 113.2(3) . . ?
C15 C14 H14 103.9 . . ?
C16 C14 H14 103.9 . . ?
C13 C14 H14 103.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C13 121.7(3) . . ?
C18 C17 H17 119.2 . . ?
C13 C17 H17 119.2 . . ?
C17 C18 C10 119.9(2) . . ?
C17 C18 H18 120.0 . . ?
C10 C18 H18 120.0 . . ?
C9 N1 C10 123.1(2) . . ?
C9 N1 H1 118.5 . . ?
C10 N1 H1 118.5 . . ?
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 C9 1.351(3) . ?
C1 C2 1.440(4) . ?
C1 Cl1 1.738(3) . ?
C2 O1 1.232(3) . ?
C2 C3 1.496(4) . ?
C3 C8 1.384(4) . ?
C3 C4 1.383(4) . ?
C4 C5 1.378(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.366(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.368(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.375(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 N1 1.341(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(3) . ?
C10 C18 1.387(3) . ?
C10 N1 1.417(3) . ?
C11 C12 1.385(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(4) . ?
C12 H12 0.9500 . ?
C13 C17 1.389(4) . ?
C13 C14 1.530(4) . ?
C14 C15 1.427(6) . ?
C14 C16 1.457(6) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.384(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N1 H1 0.8800 . ?
