#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/39/2203929.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_2203929
loop_
_publ_author_name
'Dmitry V. Albov'
'Victor B. Rybakov'
'Eugene V. Babaev'
'Leonid A. Aslanov'
_publ_section_title
1-(4-Chlorophenacyl)-4-methyl-5,6,7,8,9,10-hexahydrocycloocta[b]pyridin-2(1H)-one
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1219
_journal_page_last               o1221
_journal_paper_doi               10.1107/S1600536804014163
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C20 H22 Cl1 N1 O2'
_chemical_formula_moiety         'C20 H22 Cl1 N1 O2'
_chemical_formula_sum            'C20 H22 Cl N O2'
_chemical_formula_weight         343.84
_chemical_melting_point          454
_chemical_name_systematic
;
1-(4-Chlorophenacyl)-4-methyl-5,6,7,8,9,10-hexahydrocycloocta[b]pyridin-
2(1H)-one
;
_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                111.20(4)
_cell_angle_beta                 93.80(4)
_cell_angle_gamma                96.76(3)
_cell_formula_units_Z            2
_cell_length_a                   8.239(3)
_cell_length_b                   9.115(3)
_cell_length_c                   12.420(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      13
_cell_volume                     857.6(9)
_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 publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'κ-geometry diffractometer'
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4125
_diffrn_reflns_theta_full        27.97
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.9596
_exptl_absorpt_correction_T_min  0.9508
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.417
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0497
_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)+(0.0608P)²+0.1283P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1371
_reflns_number_gt                2645
_reflns_number_total             4125
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na6344.cif
_cod_data_source_block           3
_cod_original_formula_sum        'C20 H22 Cl1 N1 O2'
_cod_database_code               2203929
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 1.33389(8) 1.04254(8) 0.59838(6) 0.0964(3) Uani d . 1 . . Cl
N1 0.64141(17) 0.41172(18) 0.07680(13) 0.0476(4) Uani d . 1 B . N
C2 0.6811(2) 0.2867(3) -0.01743(16) 0.0548(5) Uani d . 1 . . C
O2 0.82350(19) 0.2912(2) -0.04470(14) 0.0796(5) Uani d . 1 . . O
C3 0.5491(3) 0.1621(2) -0.07632(17) 0.0608(5) Uani d . 1 . . C
H3 0.5685 0.0785 -0.1418 0.073 Uiso calc R 1 . . H
C4 0.3966(3) 0.1584(2) -0.04244(17) 0.0561(5) Uani d . 1 . . C
C5 0.3629(2) 0.2875(2) 0.05564(17) 0.0504(4) Uani d . 1 B . C
C6 0.1948(2) 0.2826(3) 0.0978(2) 0.0716(6) Uani d . 1 B . C
H6A 0.1123 0.2280 0.0313 0.086 Uiso calc R 1 . . H
H6B 0.1726 0.3907 0.1344 0.086 Uiso calc R 1 . . H
C7 0.1784(3) 0.1988(3) 0.1845(3) 0.0794(7) Uani d . 1 . . C
H7A 0.1792 0.0860 0.1431 0.095 Uiso calc R 1 A 1 H
H7B 0.0723 0.2105 0.2133 0.095 Uiso calc R 1 A 1 H
C8A 0.3144(6) 0.2599(7) 0.2908(5) 0.0729(13) Uani d P 0.719(7) B 1 C
H8A 0.2894 0.2029 0.3417 0.087 Uiso calc PR 0.719(7) B 1 H
H8B 0.4192 0.2356 0.2633 0.087 Uiso calc PR 0.719(7) B 1 H
C9A 0.3311(4) 0.4395(5) 0.3613(3) 0.0655(12) Uani d P 0.719(7) B 1 C
H9A 0.2296 0.4762 0.3455 0.079 Uiso calc PR 0.719(7) B 1 H
H9B 0.3451 0.4572 0.4435 0.079 Uiso calc PR 0.719(7) B 1 H
C8B 0.242(2) 0.3023(16) 0.2977(12) 0.081(4) Uani d P 0.281(7) B 2 C
H8C 0.2076 0.2516 0.3506 0.098 Uiso calc PR 0.281(7) B 2 H
H8D 0.1907 0.3974 0.3153 0.098 Uiso calc PR 0.281(7) B 2 H
C9B 0.4220(14) 0.3533(12) 0.3247(8) 0.072(3) Uani d P 0.281(7) B 2 C
H9C 0.4768 0.2841 0.2638 0.086 Uiso calc PR 0.281(7) B 2 H
H9D 0.4590 0.3436 0.3973 0.086 Uiso calc PR 0.281(7) B 2 H
C10 0.4726(3) 0.5382(3) 0.33565(19) 0.0690(6) Uani d . 1 . . C
H10A 0.5716 0.4929 0.3430 0.083 Uiso calc R 1 B 1 H
H10B 0.4878 0.6445 0.3951 0.083 Uiso calc R 1 B 1 H
C11 0.4572(3) 0.5533(2) 0.21700(18) 0.0590(5) Uani d . 1 B . C
H11A 0.3477 0.5763 0.2025 0.071 Uiso calc R 1 . . H
H11B 0.5348 0.6445 0.2214 0.071 Uiso calc R 1 . . H
C12 0.4854(2) 0.4123(2) 0.11367(15) 0.0457(4) Uani d . 1 . . C
C13 0.2645(3) 0.0190(3) -0.1087(2) 0.0834(8) Uani d . 1 . . C
H13A 0.1773 0.0549 -0.1431 0.125 Uiso calc R 1 . . H
H13B 0.2218 -0.0278 -0.0565 0.125 Uiso calc R 1 . . H
H13C 0.3105 -0.0589 -0.1688 0.125 Uiso calc R 1 . . H
C14 0.7792(2) 0.5373(2) 0.13958(17) 0.0537(5) Uani d . 1 . . C
H14A 0.7408 0.6397 0.1628 0.064 Uiso calc R 1 B . H
H14B 0.8626 0.5372 0.0880 0.064 Uiso calc R 1 . . H
C15 0.8549(2) 0.5165(2) 0.24609(15) 0.0453(4) Uani d . 1 B . C
O15 0.81993(17) 0.39321(16) 0.26236(12) 0.0613(4) Uani d . 1 . . O
C16 0.97150(19) 0.6526(2) 0.33139(14) 0.0431(4) Uani d D 1 . . C
C17 1.0667(2) 0.7625(2) 0.29939(16) 0.0516(4) Uani d D 1 B . C
H17 1.0552 0.7563 0.2228 0.062 Uiso calc R 1 . . H
C18 1.1790(2) 0.8814(2) 0.38171(17) 0.0617(5) Uani d D 1 . . C
H18 1.2450 0.9538 0.3602 0.074 Uiso calc R 1 B . H
C19 1.1927(2) 0.8923(2) 0.49572(17) 0.0598(5) Uani d D 1 B . C
C20 1.0981(2) 0.7855(2) 0.52950(17) 0.0618(5) Uani d D 1 . . C
H20 1.1079 0.7938 0.6066 0.074 Uiso calc R 1 B . H
C21 0.9884(2) 0.6657(2) 0.44638(15) 0.0538(5) Uani d D 1 B . C
H21 0.9244 0.5921 0.4680 0.065 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 0.0033 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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 3 5
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
C12 N1 C2 122.83(16) y
C12 N1 C14 122.10(16) y
C2 N1 C14 114.93(16) y
O2 C2 N1 119.92(19) y
O2 C2 C3 124.9(2) y
N1 C2 C3 115.15(18) y
C4 C3 C2 123.5(2) y
C4 C3 H3 118.2 n
C2 C3 H3 118.2 n
C3 C4 C5 119.16(18) y
C3 C4 C13 119.9(2) y
C5 C4 C13 120.9(2) y
C12 C5 C4 119.43(18) y
C12 C5 C6 120.56(19) n
C4 C5 C6 119.96(18) y
C5 C6 C7 113.53(18) 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
C8B C7 C6 111.3(5) y
C6 C7 C8A 115.6(2) y
C8B C7 H7A 132.0 n
C6 C7 H7A 108.4 n
C8A C7 H7A 108.4 n
C8B C7 H7B 84.6 n
C6 C7 H7B 108.4 n
C8A C7 H7B 108.4 n
H7A C7 H7B 107.4 n
C9A C8A C7 113.6(4) y
C9A C8A H8A 108.8 n
C7 C8A H8A 108.8 n
C9A C8A H8B 108.8 n
C7 C8A H8B 108.8 n
H8A C8A H8B 107.7 n
C10 C9A C8A 114.3(3) y
C10 C9A H9A 108.7 n
C8A C9A H9A 108.7 n
C10 C9A H9B 108.7 n
C8A C9A H9B 108.7 n
H9A C9A H9B 107.6 n
C7 C8B C9B 118.7(10) y
C7 C8B H8C 107.6 n
C9B C8B H8C 107.6 n
C7 C8B H8D 107.6 n
C9B C8B H8D 107.6 n
H8C C8B H8D 107.1 n
C8B C9B C10 111.3(8) y
C8B C9B H9C 109.4 n
C10 C9B H9C 109.4 n
C8B C9B H9D 109.4 n
C10 C9B H9D 109.4 n
H9C C9B H9D 108.0 n
C9A C10 C11 117.0(2) y
C11 C10 C9B 111.8(3) y
C9A C10 H10A 108.1 n
C11 C10 H10A 108.1 n
C9B C10 H10A 70.6 n
C9A C10 H10B 108.1 n
C11 C10 H10B 108.1 n
C9B C10 H10B 138.6 n
H10A C10 H10B 107.3 n
C12 C11 C10 117.23(18) y
C12 C11 H11A 108.0 n
C10 C11 H11A 108.0 n
C12 C11 H11B 108.0 n
C10 C11 H11B 108.0 n
H11A C11 H11B 107.2 n
C5 C12 N1 119.85(17) y
C5 C12 C11 122.01(18) y
N1 C12 C11 118.14(16) y
C4 C13 H13A 109.5 n
C4 C13 H13B 109.5 n
H13A C13 H13B 109.5 n
C4 C13 H13C 109.5 n
H13A C13 H13C 109.5 n
H13B C13 H13C 109.5 n
N1 C14 C15 112.31(15) y
N1 C14 H14A 109.1 n
C15 C14 H14A 109.1 n
N1 C14 H14B 109.1 n
C15 C14 H14B 109.1 n
H14A C14 H14B 107.9 n
O15 C15 C16 121.25(16) y
O15 C15 C14 120.99(16) y
C16 C15 C14 117.76(15) y
C21 C16 C17 119.21(16) n
C21 C16 C15 118.14(15) n
C17 C16 C15 122.61(16) n
C18 C17 C16 119.79(18) n
C18 C17 H17 120.1 n
C16 C17 H17 120.1 n
C19 C18 C17 119.85(18) n
C19 C18 H18 120.1 n
C17 C18 H18 120.1 n
C20 C19 C18 121.26(18) n
C20 C19 Cl1 119.35(16) n
C18 C19 Cl1 119.39(16) n
C19 C20 C21 118.48(18) n
C19 C20 H20 120.8 n
C21 C20 H20 120.8 n
C20 C21 C16 121.40(17) n
C20 C21 H21 119.3 n
C16 C21 H21 119.3 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C19 1.737(2) y
N1 C12 1.392(2) y
N1 C2 1.396(3) y
N1 C14 1.462(2) y
C2 O2 1.242(2) y
C2 C3 1.418(3) y
C3 C4 1.352(3) y
C3 H3 0.9300 n
C4 C5 1.425(3) y
C4 C13 1.509(3) y
C5 C12 1.368(3) y
C5 C6 1.514(3) y
C6 C7 1.532(4) y
C6 H6A 0.9700 n
C6 H6B 0.9700 n
C7 C8B 1.403(15) y
C7 C8A 1.560(6) y
C7 H7A 0.9700 n
C7 H7B 0.9700 n
C8A C9A 1.536(8) y
C8A H8A 0.9700 n
C8A H8B 0.9700 n
C9A C10 1.510(4) y
C9A H9A 0.9700 n
C9A H9B 0.9700 n
C8B C9B 1.48(2) y
C8B H8C 0.9700 n
C8B H8D 0.9700 n
C9B C10 1.641(10) y
C9B H9C 0.9700 n
C9B H9D 0.9700 n
C10 C11 1.527(3) y
C10 H10A 0.9700 n
C10 H10B 0.9700 n
C11 C12 1.507(3) y
C11 H11A 0.9700 n
C11 H11B 0.9700 n
C13 H13A 0.9600 n
C13 H13B 0.9600 n
C13 H13C 0.9600 n
C14 C15 1.508(3) y
C14 H14A 0.9700 n
C14 H14B 0.9700 n
C15 O15 1.217(2) y
C15 C16 1.490(3) y
C16 C21 1.386(2) y
C16 C17 1.386(2) y
C17 C18 1.383(2) y
C17 H17 0.9300 n
C18 C19 1.379(3) y
C18 H18 0.9300 n
C19 C20 1.376(2) y
C20 C21 1.380(2) y
C20 H20 0.9300 n
C21 H21 0.9300 n
