#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/18/2221874.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_2221874
loop_
_publ_author_name
'Ling, Zhang'
'Shi, Daxin'
'Yanqiu, Fan'
'Wei, Xia'
'Li, Jiarong'
_publ_section_title
;
 6'-Methyl-1',2',3',4'-tetrahydrospirocyclohexane-2'-quinazolin-4'-one
;
_journal_coeditor_code           YA2085
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1097
_journal_paper_doi               10.1107/S1600536809014111
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H18 N2 O'
_chemical_formula_moiety         'C14 H18 N2 O'
_chemical_formula_sum            'C14 H18 N2 O'
_chemical_formula_weight         230.30
_chemical_name_systematic
;
6'-Methyl-1',2',3',4'-tetrahydrospirocyclohexane-2'-quinazolin-4'-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                 106.44(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4077(19)
_cell_length_b                   11.853(2)
_cell_length_c                   11.067(2)
_cell_measurement_reflns_used    3810
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.7
_cell_volume                     1183.6(4)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.026
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14356
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         27.9
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.08
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.09
_refine_ls_R_factor_all          0.046
_refine_ls_R_factor_gt           0.039
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0601P)²+0.2329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.105
_refine_ls_wR_factor_ref         0.109
_reflns_number_gt                2346
_reflns_number_total             2810
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ya2085.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               2221874
_cod_database_fobs_code          2221874
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_type_symbol
_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
O O1 0.01942(8) 0.42294(7) 0.36579(7) 0.0182(2) Uani d . 1 . .
N N1 0.32706(11) 0.24403(8) 0.61566(9) 0.0167(2) Uani d . 1 . .
N N2 0.16255(10) 0.39739(8) 0.56703(8) 0.0144(2) Uani d . 1 . .
C C1 0.31997(12) 0.22860(9) 0.49040(10) 0.0153(2) Uani d . 1 . .
C C2 0.39770(12) 0.14331(9) 0.44884(11) 0.0191(2) Uani d . 1 . .
H H2 0.4588 0.0928 0.5078 0.023 Uiso calc R 1 . .
C C3 0.38557(12) 0.13253(9) 0.32154(11) 0.0197(2) Uani d . 1 . .
H H3 0.4379 0.0736 0.2946 0.024 Uiso calc R 1 . .
C C4 0.29853(12) 0.20585(9) 0.23162(10) 0.0180(2) Uani d . 1 . .
C C5 0.21867(12) 0.28808(9) 0.27333(10) 0.0163(2) Uani d . 1 . .
H H5 0.1573 0.3381 0.2139 0.020 Uiso calc R 1 . .
C C6 0.22636(11) 0.29905(9) 0.40055(10) 0.0143(2) Uani d . 1 . .
C C7 0.12913(11) 0.37917(9) 0.44220(10) 0.0141(2) Uani d . 1 . .
C C8 0.29082(14) 0.19553(11) 0.09415(11) 0.0268(3) Uani d . 1 . .
H H8A 0.2017 0.2339 0.0431 0.040 Uiso calc R 1 . .
H H8B 0.2869 0.1156 0.0707 0.040 Uiso calc R 1 . .
H H8C 0.3789 0.2304 0.0793 0.040 Uiso calc R 1 . .
C C9 0.30268(11) 0.35816(9) 0.65516(9) 0.0142(2) Uani d . 1 . .
C C10 0.28781(13) 0.35125(9) 0.78910(10) 0.0176(2) Uani d . 1 . .
H H10A 0.1961 0.3095 0.7872 0.021 Uiso calc R 1 . .
H H10B 0.3726 0.3080 0.8423 0.021 Uiso calc R 1 . .
C C11 0.28289(12) 0.46671(10) 0.84905(10) 0.0192(2) Uani d . 1 . .
H H11A 0.2840 0.4566 0.9381 0.023 Uiso calc R 1 . .
H H11B 0.1895 0.5055 0.8046 0.023 Uiso calc R 1 . .
C C12 0.41467(13) 0.53975(10) 0.84304(10) 0.0215(3) Uani d . 1 . .
H H12A 0.4071 0.6148 0.8799 0.026 Uiso calc R 1 . .
H H12B 0.5081 0.5040 0.8927 0.026 Uiso calc R 1 . .
C C13 0.41659(13) 0.55324(10) 0.70664(10) 0.0204(3) Uani d . 1 . .
H H13A 0.5013 0.6013 0.7029 0.024 Uiso calc R 1 . .
H H13B 0.3242 0.5906 0.6574 0.024 Uiso calc R 1 . .
C C14 0.43013(12) 0.43771(9) 0.64986(10) 0.0169(2) Uani d . 1 . .
H H14A 0.5257 0.4030 0.6963 0.020 Uiso calc R 1 . .
H H14B 0.4303 0.4474 0.5610 0.020 Uiso calc R 1 . .
H H2A 0.1067(16) 0.4493(13) 0.5919(13) 0.027(4) Uiso d . 1 . .
H H1 0.3942(18) 0.2055(13) 0.6744(14) 0.031(4) Uiso d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C9 . . 117.15(9) ?
C1 N1 H1 . . 119.1(10) ?
C9 N1 H1 . . 113.2(10) ?
C7 N2 C9 . . 122.26(9) ?
C7 N2 H2A . . 115.9(9) ?
C9 N2 H2A . . 120.1(9) ?
N1 C1 C2 . . 122.97(10) ?
N1 C1 C6 . . 118.37(10) ?
C2 C1 C6 . . 118.61(10) ?
C3 C2 C1 . . 120.00(10) ?
C3 C2 H2 . . 120.0 ?
C1 C2 H2 . . 120.0 ?
C2 C3 C4 . . 121.94(10) ?
C2 C3 H3 . . 119.0 ?
C4 C3 H3 . . 119.0 ?
C5 C4 C3 . . 117.59(10) ?
C5 C4 C8 . . 121.13(10) ?
C3 C4 C8 . . 121.28(10) ?
C4 C5 C6 . . 121.54(10) ?
C4 C5 H5 . . 119.2 ?
C6 C5 H5 . . 119.2 ?
C5 C6 C1 . . 120.19(10) ?
C5 C6 C7 . . 120.94(9) ?
C1 C6 C7 . . 118.74(9) ?
O1 C7 N2 . . 122.54(10) ?
O1 C7 C6 . . 121.44(9) ?
N2 C7 C6 . . 115.95(9) ?
C4 C8 H8A . . 109.5 ?
C4 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C4 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N1 C9 N2 . . 106.31(8) ?
N1 C9 C10 . . 107.80(8) ?
N2 C9 C10 . . 110.35(9) ?
N1 C9 C14 . . 111.48(9) ?
N2 C9 C14 . . 109.97(8) ?
C10 C9 C14 . . 110.82(9) ?
C11 C10 C9 . . 113.28(9) ?
C11 C10 H10A . . 108.9 ?
C9 C10 H10A . . 108.9 ?
C11 C10 H10B . . 108.9 ?
C9 C10 H10B . . 108.9 ?
H10A C10 H10B . . 107.7 ?
C10 C11 C12 . . 111.34(9) ?
C10 C11 H11A . . 109.4 ?
C12 C11 H11A . . 109.4 ?
C10 C11 H11B . . 109.4 ?
C12 C11 H11B . . 109.4 ?
H11A C11 H11B . . 108.0 ?
C13 C12 C11 . . 109.86(9) ?
C13 C12 H12A . . 109.7 ?
C11 C12 H12A . . 109.7 ?
C13 C12 H12B . . 109.7 ?
C11 C12 H12B . . 109.7 ?
H12A C12 H12B . . 108.2 ?
C12 C13 C14 . . 109.84(9) ?
C12 C13 H13A . . 109.7 ?
C14 C13 H13A . . 109.7 ?
C12 C13 H13B . . 109.7 ?
C14 C13 H13B . . 109.7 ?
H13A C13 H13B . . 108.2 ?
C13 C14 C9 . . 112.16(9) ?
C13 C14 H14A . . 109.2 ?
C9 C14 H14A . . 109.2 ?
C13 C14 H14B . . 109.2 ?
C9 C14 H14B . . 109.2 ?
H14A C14 H14B . . 107.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.2472(13) ?
N1 C1 . 1.3810(14) ?
N1 C9 . 1.4596(14) ?
N1 H1 . 0.893(16) ?
N2 C7 . 1.3446(13) ?
N2 C9 . 1.4757(14) ?
N2 H2A . 0.901(16) ?
C1 C2 . 1.3995(15) ?
C1 C6 . 1.4022(15) ?
C2 C3 . 1.3867(15) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.3982(17) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3870(15) ?
C4 C8 . 1.5074(15) ?
C5 C6 . 1.3953(14) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.4797(14) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C10 . 1.5299(14) ?
C9 C14 . 1.5394(15) ?
C10 C11 . 1.5273(16) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.5289(16) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.5232(16) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.5269(15) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
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
N2 H2A O1 3_566 0.901(16) 2.058(16) 2.9563(13) 174.5(13)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N1 C1 C2 . . . . 152.24(10) ?
C9 N1 C1 C6 . . . . -30.19(14) ?
N1 C1 C2 C3 . . . . 179.98(10) ?
C6 C1 C2 C3 . . . . 2.41(16) ?
C1 C2 C3 C4 . . . . 0.84(17) ?
C2 C3 C4 C5 . . . . -2.60(16) ?
C2 C3 C4 C8 . . . . 177.80(11) ?
C3 C4 C5 C6 . . . . 1.10(16) ?
C8 C4 C5 C6 . . . . -179.30(10) ?
C4 C5 C6 C1 . . . . 2.13(16) ?
C4 C5 C6 C7 . . . . -173.64(10) ?
N1 C1 C6 C5 . . . . 178.45(9) ?
C2 C1 C6 C5 . . . . -3.87(16) ?
N1 C1 C6 C7 . . . . -5.69(15) ?
C2 C1 C6 C7 . . . . 171.99(9) ?
C9 N2 C7 O1 . . . . -171.57(10) ?
C9 N2 C7 C6 . . . . 11.38(14) ?
C5 C6 C7 O1 . . . . 13.96(15) ?
C1 C6 C7 O1 . . . . -161.87(10) ?
C5 C6 C7 N2 . . . . -168.95(9) ?
C1 C6 C7 N2 . . . . 15.21(14) ?
C1 N1 C9 N2 . . . . 51.63(12) ?
C1 N1 C9 C10 . . . . 169.95(9) ?
C1 N1 C9 C14 . . . . -68.21(12) ?
C7 N2 C9 N1 . . . . -42.79(13) ?
C7 N2 C9 C10 . . . . -159.42(9) ?
C7 N2 C9 C14 . . . . 78.03(12) ?
N1 C9 C10 C11 . . . . 172.15(9) ?
N2 C9 C10 C11 . . . . -72.16(11) ?
C14 C9 C10 C11 . . . . 49.90(12) ?
C9 C10 C11 C12 . . . . -53.09(12) ?
C10 C11 C12 C13 . . . . 57.52(12) ?
C11 C12 C13 C14 . . . . -60.01(12) ?
C12 C13 C14 C9 . . . . 58.30(12) ?
N1 C9 C14 C13 . . . . -172.67(8) ?
N2 C9 C14 C13 . . . . 69.67(11) ?
C10 C9 C14 C13 . . . . -52.60(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742190
