#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/44/2204433.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_2204433
loop_
_publ_author_name
'Dmitry V. Albov'
'Victor B. Rybakov'
'Eugene V. Babaev'
'Leonid A. Aslanov'
_publ_section_title
;
 4-Methyl-1-(3-nitrophenacyl)-5,6,7,8-tetrahydroquinolin-2(1H)-one
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1952
_journal_page_last               o1953
_journal_paper_doi               10.1107/S1600536804024468
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C18 H18 N2 O4'
_chemical_formula_moiety         'C18 H18 N2 O4'
_chemical_formula_sum            'C18 H18 N2 O4'
_chemical_formula_weight         326.34
_chemical_melting_point          442
_chemical_name_systematic
;
4-methyl-1-(3-nitrophenacyl)-5,6,7,8-tetrahydroquinolin-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                92.00(2)
_cell_angle_beta                 105.09(2)
_cell_angle_gamma                118.82(2)
_cell_formula_units_Z            2
_cell_length_a                   9.115(3)
_cell_length_b                   9.271(3)
_cell_length_c                   11.248(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      12
_cell_volume                     789.5(5)
_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, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0005
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3103
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         1.91
_diffrn_standards_decay_%        8
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3103
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0704P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1288
_reflns_number_gt                1936
_reflns_number_total             3103
_reflns_threshold_expression     I>2σ(I)'
_cod_data_source_file            bt6531.cif
_cod_data_source_block           2
_cod_database_code               2204433
_cod_database_fobs_code          2204433
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
N1 0.1011(2) 0.51708(19) 0.23979(13) 0.0499(3) Uani d U 1 N
C2 -0.0685(3) 0.4844(3) 0.17853(14) 0.0508(4) Uani d U 1 C
O2 -0.1551(2) 0.3911(2) 0.07592(12) 0.0623(4) Uani d U 1 O
C3 -0.1231(3) 0.5741(2) 0.24244(17) 0.0512(4) Uani d U 1 C
H3 -0.2315 0.5646 0.2032 0.061 Uiso calc R 1 H
C4 -0.0269(3) 0.6732(2) 0.35754(16) 0.0521(4) Uani d U 1 C
C5 0.1393(3) 0.6880(2) 0.42141(16) 0.0500(3) Uani d U 1 C
C6 0.2346(3) 0.7864(3) 0.5548(2) 0.0714(5) Uani d U 1 C
H6A 0.1791 0.7170 0.6104 0.086 Uiso calc R 1 H
H6B 0.2210 0.8837 0.5605 0.086 Uiso calc R 1 H
C7 0.4317(4) 0.8452(4) 0.5999(3) 0.0863(7) Uani d U 1 C
H7A 0.4964 0.9646 0.6006 0.104 Uiso calc R 1 H
H7B 0.4619 0.8304 0.6861 0.104 Uiso calc R 1 H
C8 0.4996(4) 0.7619(4) 0.5271(3) 0.0890(8) Uani d U 1 C
H8A 0.5914 0.8508 0.5014 0.107 Uiso calc R 1 H
H8B 0.5568 0.7169 0.5865 0.107 Uiso calc R 1 H
C9 0.3813(3) 0.6262(4) 0.4140(2) 0.0720(5) Uani d U 1 C
H9A 0.3634 0.5200 0.4360 0.086 Uiso calc R 1 H
H9B 0.4386 0.6477 0.3498 0.086 Uiso calc R 1 H
C10 0.2013(2) 0.6125(2) 0.36066(16) 0.0480(3) Uani d U 1 C
C11 -0.0957(4) 0.7634(4) 0.4176(2) 0.0791(6) Uani d U 1 C
H11A -0.2134 0.7294 0.3665 0.119 Uiso calc R 1 H
H11B -0.0209 0.8821 0.4257 0.119 Uiso calc R 1 H
H11C -0.0969 0.7366 0.4991 0.119 Uiso calc R 1 H
C12 0.1657(3) 0.4367(3) 0.1718(2) 0.0578(4) Uani d U 1 C
H12A 0.2923 0.5091 0.1918 0.069 Uiso calc R 1 H
H12B 0.1127 0.4247 0.0826 0.069 Uiso calc R 1 H
C13 0.1276(2) 0.2665(2) 0.20025(13) 0.0446(3) Uani d U 1 C
O13 0.0498(2) 0.2083(2) 0.27461(14) 0.0650(4) Uani d U 1 O
C14 0.1884(2) 0.1749(2) 0.13568(13) 0.0420(3) Uani d U 1 C
C15 0.1561(2) 0.0174(2) 0.16037(18) 0.0521(4) Uani d U 1 C
H15 0.1013 -0.0253 0.2204 0.063 Uiso calc R 1 H
C16 0.2027(3) -0.0758(3) 0.0989(2) 0.0601(4) Uani d U 1 C
H16 0.1778 -0.1808 0.1169 0.072 Uiso calc R 1 H
C17 0.2861(3) -0.0158(2) 0.01074(17) 0.0550(4) Uani d U 1 C
H17 0.3172 -0.0790 -0.0320 0.066 Uiso calc R 1 H
C18 0.3221(2) 0.1415(2) -0.01210(14) 0.0455(3) Uani d U 1 C
C19 0.2735(2) 0.2377(2) 0.04819(15) 0.0443(3) Uani d U 1 C
H19 0.2980 0.3425 0.0298 0.053 Uiso calc R 1 H
N2 0.4063(2) 0.2046(2) -0.10723(14) 0.0555(3) Uani d U 1 N
O21 0.4482(2) 0.3488(2) -0.12227(16) 0.0689(4) Uani d U 1 O
O22 0.4358(3) 0.1178(3) -0.16753(17) 0.0817(5) Uani d U 1 O
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'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 -2 2
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 C10 123.62(14) y
C2 N1 C12 115.07(15) y
C10 N1 C12 121.23(16) y
O2 C2 N1 121.02(16) y
O2 C2 C3 125.00(18) y
N1 C2 C3 113.90(16) y
C4 C3 C2 123.90(18) y
C4 C3 H3 118.0 n
C2 C3 H3 118.0 n
C3 C4 C5 119.34(17) y
C3 C4 C11 120.02(19) y
C5 C4 C11 120.63(19) y
C10 C5 C4 118.61(17) y
C10 C5 C6 123.68(19) y
C4 C5 C6 117.71(17) y
C5 C6 C7 113.9(2) y
C5 C6 H6A 108.8 n
C7 C6 H6A 108.8 n
C5 C6 H6B 108.8 n
C7 C6 H6B 108.8 n
H6A C6 H6B 107.7 n
C8 C7 C6 118.4(2) y
C8 C7 H7A 107.7 n
C6 C7 H7A 107.7 n
C8 C7 H7B 107.7 n
C6 C7 H7B 107.7 n
H7A C7 H7B 107.1 n
C9 C8 C7 122.5(2) y
C9 C8 H8A 106.7 n
C7 C8 H8A 106.7 n
C9 C8 H8B 106.7 n
C7 C8 H8B 106.7 n
H8A C8 H8B 106.6 n
C8 C9 C10 112.8(2) y
C8 C9 H9A 109.0 n
C10 C9 H9A 109.0 n
C8 C9 H9B 109.0 n
C10 C9 H9B 109.0 n
H9A C9 H9B 107.8 n
C5 C10 N1 120.12(17) y
C5 C10 C9 124.37(18) y
N1 C10 C9 115.50(16) y
C4 C11 H11A 109.5 n
C4 C11 H11B 109.5 n
H11A C11 H11B 109.5 n
C4 C11 H11C 109.5 n
H11A C11 H11C 109.5 n
H11B C11 H11C 109.5 n
N1 C12 C13 114.26(15) y
N1 C12 H12A 108.7 n
C13 C12 H12A 108.7 n
N1 C12 H12B 108.7 n
C13 C12 H12B 108.7 n
H12A C12 H12B 107.6 n
O13 C13 C14 121.47(15) y
O13 C13 C12 120.32(16) y
C14 C13 C12 118.21(14) y
C19 C14 C15 118.11(15) n
C19 C14 C13 122.21(14) n
C15 C14 C13 119.66(15) n
C16 C15 C14 121.94(17) n
C16 C15 H15 119.0 n
C14 C15 H15 119.0 n
C15 C16 C17 120.69(18) n
C15 C16 H16 119.7 n
C17 C16 H16 119.7 n
C16 C17 C18 117.70(17) n
C16 C17 H17 121.2 n
C18 C17 H17 121.2 n
C17 C18 C19 122.56(16) n
C17 C18 N2 118.21(15) y
C19 C18 N2 119.15(15) y
C14 C19 C18 118.97(15) n
C14 C19 H19 120.5 n
C18 C19 H19 120.5 n
O22 N2 O21 121.65(18) y
O22 N2 C18 120.14(18) y
O21 N2 C18 118.20(14) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.391(3) y
N1 C10 1.399(2) y
N1 C12 1.450(2) y
C2 O2 1.225(3) y
C2 C3 1.414(2) y
C3 C4 1.356(3) y
C3 H3 0.9300 n
C4 C5 1.434(3) y
C4 C11 1.495(3) y
C5 C10 1.351(3) y
C5 C6 1.517(3) y
C6 C7 1.531(4) y
C6 H6A 0.9700 n
C6 H6B 0.9700 n
C7 C8 1.526(4) y
C7 H7A 0.9700 n
C7 H7B 0.9700 n
C8 C9 1.493(4) y
C8 H8A 0.9700 n
C8 H8B 0.9700 n
C9 C10 1.533(3) y
C9 H9A 0.9700 n
C9 H9B 0.9700 n
C11 H11A 0.9600 n
C11 H11B 0.9600 n
C11 H11C 0.9600 n
C12 C13 1.509(3) y
C12 H12A 0.9700 n
C12 H12B 0.9700 n
C13 O13 1.210(3) y
C13 C14 1.475(2) y
C14 C19 1.383(3) n
C14 C15 1.397(3) n
C15 C16 1.368(3) n
C15 H15 0.9300 n
C16 C17 1.376(3) n
C16 H16 0.9300 n
C17 C18 1.382(3) n
C17 H17 0.9300 n
C18 C19 1.395(2) n
C18 N2 1.454(3) y
C19 H19 0.9300 n
N2 O22 1.202(2) y
N2 O21 1.233(2) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130356
