#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/37/2203794.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2203794
loop_
_publ_author_name
'Dmitry V. Albov'
'Victor B. Rybakov'
'Eugene V. Babaev'
'Leonid A. Aslanov'
_publ_section_title
2-(4-Chlorophenacyloxy)-4-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1098
_journal_page_last               o1099
_journal_paper_doi               10.1107/S1600536804012450
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C19 H20 Cl N O2'
_chemical_formula_moiety         'C19 H20 Cl N O2'
_chemical_formula_sum            'C19 H20 Cl N O2'
_chemical_formula_weight         329.81
_chemical_melting_point          466
_chemical_name_systematic
;
2-(4-chlorophenacyl)oxy-4-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                94.390(10)
_cell_angle_beta                 98.02(2)
_cell_angle_gamma                94.56(2)
_cell_formula_units_Z            2
_cell_length_a                   6.2691(16)
_cell_length_b                   9.2424(10)
_cell_length_c                   14.926(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35
_cell_measurement_theta_min      32
_cell_volume                     850.3(3)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device       κ--geometry
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'non-profiled ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine--focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3409
_diffrn_reflns_theta_full        74.91
_diffrn_reflns_theta_max         74.91
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    2.056
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3409
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0496
_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)+(0.1026P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1436
_reflns_number_gt                2390
_reflns_number_total             3409
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na6333.cif
_cod_data_source_block           2
_cod_original_formula_sum        'C19 H20 Cl1 N1 O2'
_cod_database_code               2203794
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Cl1 0.26276(13) 0.68708(10) 1.03550(4) 0.1341(3) Uani d . 1 Cl
N1 0.8708(2) 0.28776(18) 0.67027(9) 0.0780(4) Uani d . 1 N
C2 0.8640(3) 0.3342(2) 0.58988(11) 0.0693(4) Uani d . 1 C
O2 0.71771(19) 0.43019(15) 0.56459(7) 0.0758(3) Uani d . 1 O
C3 0.9974(3) 0.29254(19) 0.52746(10) 0.0689(4) Uani d . 1 C
H3 0.9862 0.3301 0.4711 0.083 Uiso calc R 1 H
C4 1.1437(3) 0.1968(2) 0.54966(11) 0.0776(5) Uani d . 1 C
C5 1.1857(2) 0.17016(15) 0.64165(9) 0.0521(3) Uani d . 1 C
C6 1.3717(2) 0.08038(17) 0.67629(11) 0.0617(4) Uani d . 1 C
H6A 1.4620 0.1359 0.7275 0.074 Uiso calc R 1 H
H6B 1.4601 0.0649 0.6286 0.074 Uiso calc R 1 H
C7 1.2933(3) -0.07083(18) 0.70624(12) 0.0695(4) Uani d . 1 C
H7A 1.1744 -0.1148 0.6613 0.083 Uiso calc R 1 H
H7B 1.4103 -0.1334 0.7061 0.083 Uiso calc R 1 H
C8 1.2189(3) -0.0669(2) 0.80008(12) 0.0696(4) Uani d . 1 C
H8A 1.1824 -0.1664 0.8131 0.084 Uiso calc R 1 H
H8B 1.3398 -0.0265 0.8451 0.084 Uiso calc R 1 H
C9 1.0281(3) 0.01906(18) 0.81154(11) 0.0675(4) Uani d . 1 C
H9A 0.9913 0.0093 0.8719 0.081 Uiso calc R 1 H
H9B 0.9051 -0.0233 0.7682 0.081 Uiso calc R 1 H
C10 1.0655(2) 0.18374(16) 0.79847(9) 0.0590(3) Uani d . 1 C
H10A 0.9599 0.2346 0.8272 0.071 Uiso calc R 1 H
H10B 1.2076 0.2202 0.8302 0.071 Uiso calc R 1 H
C11 1.0509(2) 0.22179(17) 0.70138(10) 0.0586(3) Uani d . 1 C
C12 1.2884(4) 0.1475(3) 0.48177(13) 0.0925(6) Uani d . 1 C
H12A 1.2639 0.2002 0.4289 0.139 Uiso calc R 1 H
H12B 1.2556 0.0450 0.4646 0.139 Uiso calc R 1 H
H12C 1.4371 0.1660 0.5089 0.139 Uiso calc R 1 H
C13 0.5801(3) 0.4687(2) 0.62920(11) 0.0777(5) Uani d . 1 C
H13A 0.5232 0.3810 0.6527 0.093 Uiso calc R 1 H
H13B 0.4588 0.5142 0.5991 0.093 Uiso calc R 1 H
C14 0.6963(3) 0.5719(2) 0.70745(11) 0.0719(4) Uani d . 1 C
O14 0.8741(2) 0.63404(17) 0.70412(9) 0.0901(4) Uani d . 1 O
C15 0.5826(3) 0.5960(2) 0.78816(11) 0.0713(4) Uani d . 1 C
C16 0.6920(3) 0.6843(2) 0.86318(12) 0.0865(5) Uani d . 1 C
H16 0.8328 0.7241 0.8625 0.104 Uiso calc R 1 H
C17 0.5915(5) 0.7125(3) 0.93833(15) 0.1089(8) Uani d . 1 C
H17 0.6630 0.7737 0.9876 0.131 Uiso calc R 1 H
C18 0.3885(5) 0.6512(3) 0.94061(15) 0.1043(7) Uani d . 1 C
C19 0.2739(4) 0.5622(3) 0.86688(17) 0.1092(8) Uani d . 1 C
H19 0.1346 0.5209 0.8686 0.131 Uiso calc R 1 H
C20 0.3751(3) 0.5376(3) 0.79105(14) 0.0876(6) Uani d . 1 C
H20 0.3008 0.4800 0.7408 0.105 Uiso calc R 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 2 10
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C11 116.25(14) y
N1 C2 O2 118.48(15) y
N1 C2 C3 124.24(16) y
O2 C2 C3 117.28(14) y
C2 O2 C13 116.07(13) y
C4 C3 C2 119.13(15) y
C4 C3 H3 120.4 n
C2 C3 H3 120.4 n
C3 C4 C5 117.02(15) y
C3 C4 C12 120.04(16) y
C5 C4 C12 121.64(16) y
C11 C5 C4 119.09(14) y
C11 C5 C6 119.80(13) y
C4 C5 C6 121.06(13) y
C5 C6 C7 113.56(12) y
C5 C6 H6A 108.9 n
C7 C6 H6A 108.9 n
C5 C6 H6B 108.9 n
C7 C6 H6B 108.9 n
H6A C6 H6B 107.7 n
C8 C7 C6 115.37(14) y
C8 C7 H7A 108.4 n
C6 C7 H7A 108.4 n
C8 C7 H7B 108.4 n
C6 C7 H7B 108.4 n
H7A C7 H7B 107.5 n
C9 C8 C7 116.06(14) y
C9 C8 H8A 108.3 n
C7 C8 H8A 108.3 n
C9 C8 H8B 108.3 n
C7 C8 H8B 108.3 n
H8A C8 H8B 107.4 n
C8 C9 C10 114.70(14) y
C8 C9 H9A 108.6 n
C10 C9 H9A 108.6 n
C8 C9 H9B 108.6 n
C10 C9 H9B 108.6 n
H9A C9 H9B 107.6 n
C11 C10 C9 115.80(13) y
C11 C10 H10A 108.3 n
C9 C10 H10A 108.3 n
C11 C10 H10B 108.3 n
C9 C10 H10B 108.3 n
H10A C10 H10B 107.4 n
N1 C11 C5 120.78(13) y
N1 C11 C10 115.02(12) y
C5 C11 C10 123.12(13) y
C4 C12 H12A 109.5 n
C4 C12 H12B 109.5 n
H12A C12 H12B 109.5 n
C4 C12 H12C 109.5 n
H12A C12 H12C 109.5 n
H12B C12 H12C 109.5 n
O2 C13 C14 112.46(15) y
O2 C13 H13A 109.1 n
C14 C13 H13A 109.1 n
O2 C13 H13B 109.1 n
C14 C13 H13B 109.1 n
H13A C13 H13B 107.8 n
O14 C14 C15 121.64(17) y
O14 C14 C13 121.29(16) y
C15 C14 C13 117.06(15) y
C20 C15 C16 118.90(18) n
C20 C15 C14 123.11(17) n
C16 C15 C14 117.97(17) n
C17 C16 C15 120.0(2) n
C17 C16 H16 120.0 n
C15 C16 H16 120.0 n
C18 C17 C16 120.2(2) n
C18 C17 H17 119.9 n
C16 C17 H17 119.9 n
C17 C18 C19 121.5(2) n
C17 C18 Cl1 120.0(2) n
C19 C18 Cl1 118.5(2) n
C20 C19 C18 117.7(2) n
C20 C19 H19 121.1 n
C18 C19 H19 121.1 n
C15 C20 C19 121.7(2) n
C15 C20 H20 119.1 n
C19 C20 H20 119.1 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C18 1.737(2) y
N1 C2 1.301(2) y
N1 C11 1.3671(19) y
C2 O2 1.362(2) y
C2 C3 1.389(2) y
O2 C13 1.425(2) y
C3 C4 1.350(2) y
C3 H3 0.9300 n
C4 C5 1.406(2) y
C4 C12 1.520(2) y
C5 C11 1.3948(19) y
C5 C6 1.539(2) y
C6 C7 1.563(2) y
C6 H6A 0.9700 n
C6 H6B 0.9700 n
C7 C8 1.536(2) y
C7 H7A 0.9700 n
C7 H7B 0.9700 n
C8 C9 1.509(2) y
C8 H8A 0.9700 n
C8 H8B 0.9700 n
C9 C10 1.553(2) y
C9 H9A 0.9700 n
C9 H9B 0.9700 n
C10 C11 1.5094(19) y
C10 H10A 0.9700 n
C10 H10B 0.9700 n
C12 H12A 0.9600 n
C12 H12B 0.9600 n
C12 H12C 0.9600 n
C13 C14 1.512(3) y
C13 H13A 0.9700 n
C13 H13B 0.9700 n
C14 O14 1.222(2) y
C14 C15 1.494(2) y
C15 C20 1.376(3) y
C15 C16 1.395(3) y
C16 C17 1.379(3) y
C16 H16 0.9300 n
C17 C18 1.357(4) y
C17 H17 0.9300 n
C18 C19 1.397(4) y
C19 C20 1.385(3) y
C19 H19 0.9300 n
C20 H20 0.9300 n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130756
2 PubChem 139066762
