#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/65/2206513.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_2206513
loop_
_publ_author_name
'Yun Liu'
'Zhi-Feng Lu'
'Yong-Miao Shen'
'Jian-Hua Xu'
_publ_section_title
;
 3-Benzoylmethylene-1-methyl-3,4-dihydroquinoxalin-2(1H)-one
;
_journal_coeditor_code           OB6546
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2753
_journal_page_last               o2754
_journal_paper_doi               10.1107/S1600536805023664
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C17 H14 N2 O2'
_chemical_formula_moiety         'C17 H14 N2 O2'
_chemical_formula_sum            'C17 H14 N2 O2'
_chemical_formula_weight         278.30
_chemical_melting_point          455.2
_chemical_name_systematic
;
3-Benzoylmethylene-1-methyl-3,4-dihydroquinoxalin-2(1H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 104.36(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6050(19)
_cell_length_b                   10.767(2)
_cell_length_c                   13.374(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    288(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1339.9(5)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      288(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0681
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2510
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.36
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XCAD4; Harms & Wocadlo, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.168
_refine_ls_extinction_coef       0.0139(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0457
_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)+(0.03P)²+0.49P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1074
_reflns_number_gt                1356
_reflns_number_total             2363
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6546.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2206513
_cod_database_fobs_code          2206513
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_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
O1 0.00304(16) 0.06650(15) 0.16468(12) 0.0581(5) Uani d . 1 O
O2 -0.24468(17) 0.23386(16) -0.18275(12) 0.0651(5) Uani d . 1 O
N1 0.04478(17) 0.24784(16) 0.04098(13) 0.0462(5) Uani d . 1 N
H1N 0.0760 0.2120 0.0998 0.055 Uiso calc R 1 H
N2 -0.05516(19) 0.36626(17) -0.14523(13) 0.0482(5) Uani d . 1 N
C1 -0.4216(3) -0.1813(3) 0.0887(2) 0.0778(8) Uani d . 1 C
H1 -0.5135 -0.1962 0.0478 0.093 Uiso calc R 1 H
C2 -0.3382(3) -0.0883(2) 0.0615(2) 0.0670(7) Uani d . 1 C
H2 -0.3743 -0.0425 0.0017 0.080 Uiso calc R 1 H
C3 -0.2023(2) -0.0626(2) 0.12186(17) 0.0454(5) Uani d . 1 C
C4 -0.1502(3) -0.1347(2) 0.20900(18) 0.0577(7) Uani d . 1 C
H4 -0.0587 -0.1198 0.2505 0.069 Uiso calc R 1 H
C5 -0.2339(3) -0.2290(2) 0.2349(2) 0.0674(7) Uani d . 1 C
H5 -0.1975 -0.2773 0.2932 0.081 Uiso calc R 1 H
C6 -0.3698(3) -0.2512(2) 0.1752(2) 0.0708(8) Uani d . 1 C
H6 -0.4261 -0.3134 0.1934 0.085 Uiso calc R 1 H
C7 -0.1108(2) 0.0408(2) 0.09837(17) 0.0456(5) Uani d . 1 C
C8 -0.1543(2) 0.1075(2) 0.00396(17) 0.0484(6) Uani d . 1 C
H8 -0.2387 0.0835 -0.0430 0.058 Uiso calc R 1 H
C9 -0.0782(2) 0.2057(2) -0.02150(17) 0.0444(5) Uani d . 1 C
C10 -0.1337(2) 0.2684(2) -0.12237(18) 0.0479(6) Uani d . 1 C
C11 -0.1089(3) 0.4298(2) -0.24449(17) 0.0686(7) Uani d . 1 C
H11A -0.1977 0.3924 -0.2810 0.103 Uiso calc R 1 H
H11B -0.0394 0.4225 -0.2849 0.103 Uiso calc R 1 H
H11C -0.1246 0.5160 -0.2325 0.103 Uiso calc R 1 H
C12 0.0747(2) 0.40568(19) -0.07831(16) 0.0427(5) Uani d . 1 C
C13 0.1558(2) 0.5028(2) -0.10307(18) 0.0515(6) Uani d . 1 C
H13 0.1250 0.5434 -0.1661 0.062 Uiso calc R 1 H
C14 0.2809(2) 0.5388(2) -0.03505(19) 0.0593(7) Uani d . 1 C
H14 0.3339 0.6041 -0.0524 0.071 Uiso calc R 1 H
C15 0.3291(3) 0.4800(2) 0.0584(2) 0.0620(7) Uani d . 1 C
H15 0.4140 0.5054 0.1041 0.074 Uiso calc R 1 H
C16 0.2512(2) 0.3833(2) 0.08401(18) 0.0548(6) Uani d . 1 C
H16 0.2836 0.3429 0.1470 0.066 Uiso calc R 1 H
C17 0.1244(2) 0.3457(2) 0.01627(17) 0.0436(5) Uani d . 1 C
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C9 N1 C17 123.96(19) yes
C9 N1 H1N 118.0 ?
C17 N1 H1N 118.0 ?
C10 N2 C12 122.57(19) yes
C10 N2 C11 117.99(19) ?
C12 N2 C11 119.43(19) ?
C6 C1 C2 120.5(3) ?
C6 C1 H1 119.7 ?
C2 C1 H1 119.7 ?
C3 C2 C1 120.9(3) ?
C3 C2 H2 119.5 ?
C1 C2 H2 119.5 ?
C2 C3 C4 118.1(2) ?
C2 C3 C7 122.9(2) ?
C4 C3 C7 119.0(2) ?
C3 C4 C5 120.5(2) ?
C3 C4 H4 119.7 ?
C5 C4 H4 119.7 ?
C6 C5 C4 120.5(3) ?
C6 C5 H5 119.8 ?
C4 C5 H5 119.8 ?
C1 C6 C5 119.4(2) ?
C1 C6 H6 120.3 ?
C5 C6 H6 120.3 ?
O1 C7 C8 121.9(2) yes
O1 C7 C3 117.9(2) yes
C8 C7 C3 120.2(2) yes
C9 C8 C7 123.4(2) yes
C9 C8 H8 118.3 ?
C7 C8 H8 118.3 ?
N1 C9 C8 123.0(2) ?
N1 C9 C10 118.2(2) ?
C8 C9 C10 118.81(19) ?
O2 C10 N2 121.5(2) yes
O2 C10 C9 121.2(2) yes
N2 C10 C9 117.28(19) ?
N2 C11 H11A 109.5 ?
N2 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
N2 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
C13 C12 C17 118.5(2) ?
C13 C12 N2 122.3(2) ?
C17 C12 N2 119.2(2) ?
C14 C13 C12 120.3(2) ?
C14 C13 H13 119.8 ?
C12 C13 H13 119.8 ?
C13 C14 C15 121.0(2) ?
C13 C14 H14 119.5 ?
C15 C14 H14 119.5 ?
C16 C15 C14 119.6(2) ?
C16 C15 H15 120.2 ?
C14 C15 H15 120.2 ?
C15 C16 C17 120.2(2) ?
C15 C16 H16 119.9 ?
C17 C16 H16 119.9 ?
C16 C17 N1 120.8(2) ?
C16 C17 C12 120.4(2) ?
N1 C17 C12 118.8(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 1.256(2) yes
O2 C10 1.225(2) yes
N1 C9 1.345(2) yes
N1 C17 1.389(3) yes
N1 H1N 0.8600 ?
N2 C10 1.373(3) yes
N2 C12 1.408(3) yes
N2 C11 1.468(3) yes
C1 C6 1.367(4) ?
C1 C2 1.387(3) ?
C1 H1 0.9300 ?
C2 C3 1.383(3) ?
C2 H2 0.9300 ?
C3 C4 1.386(3) ?
C3 C7 1.499(3) yes
C4 C5 1.392(3) ?
C4 H4 0.9300 ?
C5 C6 1.371(3) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 C8 1.423(3) yes
C8 C9 1.375(3) yes
C8 H8 0.9300 ?
C9 C10 1.484(3) ?
C11 H11A 0.9600 ?
C11 H11B 0.9600 ?
C11 H11C 0.9600 ?
C12 C13 1.392(3) ?
C12 C17 1.395(3) ?
C13 C14 1.371(3) ?
C13 H13 0.9300 ?
C14 C15 1.376(3) ?
C14 H14 0.9300 ?
C15 C16 1.374(3) ?
C15 H15 0.9300 ?
C16 C17 1.385(3) ?
C16 H16 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1N O1 . 0.86 2.00 2.653(2) 132 yes
C6 H6 O1 2_445 0.93 2.55 3.382(3) 149 yes
C16 H16 O2 4_666 0.93 2.50 3.356(3) 153 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.2(4) ?
C1 C2 C3 C4 1.6(4) ?
C1 C2 C3 C7 -177.0(2) ?
C2 C3 C4 C5 -0.7(3) ?
C7 C3 C4 C5 178.0(2) ?
C3 C4 C5 C6 -0.7(4) ?
C2 C1 C6 C5 -0.2(4) ?
C4 C5 C6 C1 1.2(4) ?
C2 C3 C7 O1 171.1(2) ?
C4 C3 C7 O1 -7.5(3) ?
C2 C3 C7 C8 -8.2(3) yes
C4 C3 C7 C8 173.2(2) ?
O1 C7 C8 C9 -1.2(3) ?
C3 C7 C8 C9 178.0(2) yes
C17 N1 C9 C8 179.1(2) ?
C17 N1 C9 C10 -0.9(3) ?
C7 C8 C9 N1 -0.1(3) yes
C7 C8 C9 C10 179.9(2) ?
C12 N2 C10 O2 -178.3(2) ?
C11 N2 C10 O2 0.6(3) ?
C12 N2 C10 C9 1.4(3) ?
C11 N2 C10 C9 -179.70(19) ?
N1 C9 C10 O2 179.62(19) ?
C8 C9 C10 O2 -0.4(3) ?
N1 C9 C10 N2 -0.1(3) ?
C8 C9 C10 N2 179.87(19) ?
C10 N2 C12 C13 178.3(2) ?
C11 N2 C12 C13 -0.6(3) ?
C10 N2 C12 C17 -1.7(3) ?
C11 N2 C12 C17 179.4(2) ?
C17 C12 C13 C14 -0.7(3) ?
N2 C12 C13 C14 179.3(2) ?
C12 C13 C14 C15 0.3(4) ?
C13 C14 C15 C16 0.2(4) ?
C14 C15 C16 C17 -0.3(4) ?
C15 C16 C17 N1 179.8(2) ?
C15 C16 C17 C12 -0.1(3) ?
C9 N1 C17 C16 -179.3(2) ?
C9 N1 C17 C12 0.7(3) ?
C13 C12 C17 C16 0.6(3) ?
N2 C12 C17 C16 -179.41(19) ?
C13 C12 C17 N1 -179.33(19) ?
N2 C12 C17 N1 0.6(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21180454
