#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/07/2230771.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_2230771
loop_
_publ_author_name
'Tang, Jianhong'
'Shi, Daxin'
'Yan, Liupan'
'Liu, Xuan'
'Li, Jiarong'
_publ_section_title
;
 5'-Methyl-4'-oxo-7'-phenyl-3',4'-dihydro-1'H-spiro[cyclohexane-1,2'-quinazoline]-8'-carbonitrile
;
_journal_coeditor_code           LD2014
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1672
_journal_paper_doi               10.1107/S160053681102188X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C21 H21 N3 O'
_chemical_formula_moiety         'C21 H21 N3 O'
_chemical_formula_sum            'C21 H21 N3 O'
_chemical_formula_weight         331.41
_chemical_name_systematic
;
5'-Methyl-4'-oxo-7'-phenyl-3',4'-dihydro-1'H-spiro[cyclohexane-1,2'-
quinazoline]-8'-carbonitrile
;
_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           SHELXL97
_cell_angle_alpha                101.858(8)
_cell_angle_beta                 93.794(9)
_cell_angle_gamma                104.606(9)
_cell_formula_units_Z            2
_cell_length_a                   7.1824(15)
_cell_length_b                   11.233(3)
_cell_length_c                   11.430(3)
_cell_measurement_reflns_used    3260
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      29.126
_cell_measurement_theta_min      2.950
_cell_volume                     866.5(4)
_computing_cell_refinement       'CrystalClear (Rigaku, 2004)'
_computing_data_collection       'CrystalClear (Rigaku, 2004)'
_computing_data_reduction        'CrystalClear (Rigaku, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Rigaku AFC10/Saturn724+'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9387
_diffrn_reflns_theta_full        29.12
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_min         2.95
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.202
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0479
_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)+(0.0516P)²+0.2590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1168
_reflns_number_gt                3511
_reflns_number_total             4521
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ld2014.cif
_cod_data_source_block           I
_cod_original_cell_volume        866.6(4)
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_database_code               2230771
_cod_database_fobs_code          2230771
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.79935(15) 0.44593(8) 0.06825(9) 0.0303(2) Uani d . 1 1 . .
N N1 0.97094(15) 0.77778(10) 0.30982(9) 0.0212(2) Uani d . 1 1 . .
N N2 1.00920(15) 0.63845(9) 0.13608(9) 0.0201(2) Uani d . 1 1 . .
N N3 0.84792(18) 0.93552(12) 0.57411(11) 0.0336(3) Uani d . 1 1 . .
C C1 1.26985(18) 0.83252(12) 0.22053(11) 0.0212(3) Uani d . 1 1 . .
H H1A 1.3292 0.7806 0.2637 0.025 Uiso calc R 1 1 . .
H H1B 1.2955 0.9177 0.2742 0.025 Uiso calc R 1 1 . .
C C2 1.36630(19) 0.84416(12) 0.10637(12) 0.0250(3) Uani d . 1 1 . .
H H2A 1.5044 0.8920 0.1293 0.030 Uiso calc R 1 1 . .
H H2B 1.3612 0.7587 0.0593 0.030 Uiso calc R 1 1 . .
C C3 1.2676(2) 0.91080(13) 0.02799(13) 0.0290(3) Uani d . 1 1 . .
H H3A 1.3260 0.9095 -0.0482 0.035 Uiso calc R 1 1 . .
H H3B 1.2883 1.0002 0.0704 0.035 Uiso calc R 1 1 . .
C C4 1.0504(2) 0.84591(13) -0.00007(12) 0.0255(3) Uani d . 1 1 . .
H H4A 1.0296 0.7585 -0.0479 0.031 Uiso calc R 1 1 . .
H H4B 0.9881 0.8920 -0.0488 0.031 Uiso calc R 1 1 . .
C C5 0.95716(18) 0.84267(11) 0.11605(11) 0.0214(3) Uani d . 1 1 . .
H H5A 0.8168 0.7998 0.0958 0.026 Uiso calc R 1 1 . .
H H5B 0.9719 0.9302 0.1617 0.026 Uiso calc R 1 1 . .
C C6 1.05070(17) 0.77279(11) 0.19470(10) 0.0179(2) Uani d . 1 1 . .
C C7 0.78933(17) 0.70442(11) 0.31283(10) 0.0185(2) Uani d . 1 1 . .
C C8 0.68158(18) 0.73621(11) 0.40828(11) 0.0193(2) Uani d . 1 1 . .
C C9 0.49368(18) 0.66095(12) 0.41115(11) 0.0203(2) Uani d . 1 1 . .
C C10 0.41853(19) 0.55284(12) 0.31972(12) 0.0242(3) Uani d . 1 1 . .
H H10 0.2911 0.5021 0.3205 0.029 Uiso calc R 1 1 . .
C C11 0.52333(19) 0.51594(12) 0.22663(12) 0.0234(3) Uani d . 1 1 . .
C C12 0.71034(18) 0.59166(11) 0.22332(10) 0.0190(2) Uani d . 1 1 . .
C C13 0.83918(18) 0.55304(11) 0.13493(11) 0.0203(2) Uani d . 1 1 . .
C C14 0.77055(18) 0.84636(12) 0.50192(11) 0.0224(3) Uani d . 1 1 . .
C C15 0.4289(2) 0.39423(14) 0.13529(14) 0.0364(4) Uani d . 1 1 . .
H H15A 0.4901 0.3288 0.1491 0.044 Uiso calc R 1 1 . .
H H15B 0.4446 0.4074 0.0540 0.044 Uiso calc R 1 1 . .
H H15C 0.2905 0.3674 0.1434 0.044 Uiso calc R 1 1 . .
C C16 0.37353(18) 0.69620(13) 0.50673(11) 0.0228(3) Uani d . 1 1 . .
C C17 0.3629(2) 0.82022(14) 0.54351(12) 0.0281(3) Uani d . 1 1 . .
H H17 0.4364 0.8841 0.5090 0.034 Uiso calc R 1 1 . .
C C18 0.2455(2) 0.85120(17) 0.63036(13) 0.0377(4) Uani d . 1 1 . .
H H18 0.2394 0.9361 0.6553 0.045 Uiso calc R 1 1 . .
C C19 0.1375(2) 0.75827(19) 0.68029(14) 0.0431(4) Uani d . 1 1 . .
H H19 0.0572 0.7793 0.7396 0.052 Uiso calc R 1 1 . .
C C20 0.1462(2) 0.63526(18) 0.64427(14) 0.0413(4) Uani d . 1 1 . .
H H20 0.0718 0.5717 0.6789 0.050 Uiso calc R 1 1 . .
C C21 0.2633(2) 0.60356(15) 0.55756(13) 0.0314(3) Uani d . 1 1 . .
H H21 0.2681 0.5184 0.5329 0.038 Uiso calc R 1 1 . .
H H2N 1.081(2) 0.6152(15) 0.0762(15) 0.034(4) Uiso d . 1 1 . .
H H1N 1.012(3) 0.8526(17) 0.3587(16) 0.039(5) Uiso d . 1 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
C7 N1 C6 . . 119.48(10) ?
C7 N1 H1N . . 119.5(11) ?
C6 N1 H1N . . 112.5(11) ?
C13 N2 C6 . . 123.65(10) ?
C13 N2 H2N . . 114.8(10) ?
C6 N2 H2N . . 118.2(10) ?
C6 C1 C2 . . 113.08(10) ?
C6 C1 H1A . . 109.0 ?
C2 C1 H1A . . 109.0 ?
C6 C1 H1B . . 109.0 ?
C2 C1 H1B . . 109.0 ?
H1A C1 H1B . . 107.8 ?
C3 C2 C1 . . 111.97(11) ?
C3 C2 H2A . . 109.2 ?
C1 C2 H2A . . 109.2 ?
C3 C2 H2B . . 109.2 ?
C1 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
C2 C3 C4 . . 110.60(11) ?
C2 C3 H3A . . 109.5 ?
C4 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
C4 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.1 ?
C3 C4 C5 . . 110.76(11) ?
C3 C4 H4A . . 109.5 ?
C5 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
C5 C4 H4B . . 109.5 ?
H4A C4 H4B . . 108.1 ?
C4 C5 C6 . . 111.17(10) ?
C4 C5 H5A . . 109.4 ?
C6 C5 H5A . . 109.4 ?
C4 C5 H5B . . 109.4 ?
C6 C5 H5B . . 109.4 ?
H5A C5 H5B . . 108.0 ?
N2 C6 N1 . . 106.03(9) ?
N2 C6 C1 . . 110.11(9) ?
N1 C6 C1 . . 108.50(10) ?
N2 C6 C5 . . 110.77(10) ?
N1 C6 C5 . . 111.09(10) ?
C1 C6 C5 . . 110.24(10) ?
N1 C7 C12 . . 119.96(10) ?
N1 C7 C8 . . 120.76(10) ?
C12 C7 C8 . . 119.21(11) ?
C9 C8 C7 . . 120.81(11) ?
C9 C8 C14 . . 121.21(10) ?
C7 C8 C14 . . 117.97(11) ?
C10 C9 C8 . . 118.30(11) ?
C10 C9 C16 . . 119.88(11) ?
C8 C9 C16 . . 121.80(11) ?
C9 C10 C11 . . 122.48(12) ?
C9 C10 H10 . . 118.8 ?
C11 C10 H10 . . 118.8 ?
C10 C11 C12 . . 119.18(11) ?
C10 C11 C15 . . 117.49(12) ?
C12 C11 C15 . . 123.33(11) ?
C11 C12 C7 . . 119.93(10) ?
C11 C12 C13 . . 122.62(10) ?
C7 C12 C13 . . 117.22(11) ?
O1 C13 N2 . . 121.02(11) ?
O1 C13 C12 . . 122.42(11) ?
N2 C13 C12 . . 116.43(10) ?
N3 C14 C8 . . 177.19(13) ?
C11 C15 H15A . . 109.5 ?
C11 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C11 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C17 C16 C21 . . 118.90(12) ?
C17 C16 C9 . . 121.09(12) ?
C21 C16 C9 . . 119.96(12) ?
C18 C17 C16 . . 120.52(14) ?
C18 C17 H17 . . 119.7 ?
C16 C17 H17 . . 119.7 ?
C19 C18 C17 . . 119.88(15) ?
C19 C18 H18 . . 120.1 ?
C17 C18 H18 . . 120.1 ?
C20 C19 C18 . . 120.13(13) ?
C20 C19 H19 . . 119.9 ?
C18 C19 H19 . . 119.9 ?
C19 C20 C21 . . 120.33(15) ?
C19 C20 H20 . . 119.8 ?
C21 C20 H20 . . 119.8 ?
C20 C21 C16 . . 120.24(15) ?
C20 C21 H21 . . 119.9 ?
C16 C21 H21 . . 119.9 ?
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 C13 . 1.2374(14) ?
N1 C7 . 1.3628(16) ?
N1 C6 . 1.4658(15) ?
N1 H1N . 0.875(18) ?
N2 C13 . 1.3468(16) ?
N2 C6 . 1.4650(15) ?
N2 H2N . 0.920(17) ?
N3 C14 . 1.1453(17) ?
C1 C6 . 1.5295(17) ?
C1 C2 . 1.5310(17) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C3 . 1.525(2) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C4 . 1.5268(19) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C5 . 1.5288(17) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.5335(18) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C7 C12 . 1.4147(16) ?
C7 C8 . 1.4169(15) ?
C8 C9 . 1.4068(17) ?
C8 C14 . 1.4323(17) ?
C9 C10 . 1.3898(17) ?
C9 C16 . 1.4881(16) ?
C10 C11 . 1.3974(17) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.4045(17) ?
C11 C15 . 1.5071(18) ?
C12 C13 . 1.4870(16) ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 C17 . 1.3931(19) ?
C16 C21 . 1.3933(19) ?
C17 C18 . 1.3909(18) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.383(3) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.377(3) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.3901(19) ?
C20 H20 . 0.9500 ?
C21 H21 . 0.9500 ?
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
N2 H2N Ol 2_765 0.920(17) 1.998(14) 2.9010(17) 171.68(14) y
N1 H1N N3 2_776 0.875(18) 2.281(14) 3.1188(19) 160.24(15) y
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
C6 C1 C2 C3 . . . . 52.46(14) ?
C1 C2 C3 C4 . . . . -53.99(14) ?
C2 C3 C4 C5 . . . . 57.35(14) ?
C3 C4 C5 C6 . . . . -58.74(14) ?
C13 N2 C6 N1 . . . . 41.95(15) ?
C13 N2 C6 C1 . . . . 159.13(11) ?
C13 N2 C6 C5 . . . . -78.67(14) ?
C7 N1 C6 N2 . . . . -45.90(14) ?
C7 N1 C6 C1 . . . . -164.16(10) ?
C7 N1 C6 C5 . . . . 74.51(14) ?
C2 C1 C6 N2 . . . . 69.94(13) ?
C2 C1 C6 N1 . . . . -174.42(10) ?
C2 C1 C6 C5 . . . . -52.57(13) ?
C4 C5 C6 N2 . . . . -66.58(13) ?
C4 C5 C6 N1 . . . . 175.86(10) ?
C4 C5 C6 C1 . . . . 55.55(13) ?
C6 N1 C7 C12 . . . . 25.46(17) ?
C6 N1 C7 C8 . . . . -157.79(11) ?
N1 C7 C8 C9 . . . . 179.65(11) ?
C12 C7 C8 C9 . . . . -3.57(18) ?
N1 C7 C8 C14 . . . . -0.92(18) ?
C12 C7 C8 C14 . . . . 175.86(11) ?
C7 C8 C9 C10 . . . . 1.68(18) ?
C14 C8 C9 C10 . . . . -177.73(12) ?
C7 C8 C9 C16 . . . . -176.57(12) ?
C14 C8 C9 C16 . . . . 4.01(19) ?
C8 C9 C10 C11 . . . . 0.8(2) ?
C16 C9 C10 C11 . . . . 179.05(12) ?
C9 C10 C11 C12 . . . . -1.3(2) ?
C9 C10 C11 C15 . . . . 177.78(13) ?
C10 C11 C12 C7 . . . . -0.69(19) ?
C15 C11 C12 C7 . . . . -179.68(13) ?
C10 C11 C12 C13 . . . . 173.71(12) ?
C15 C11 C12 C13 . . . . -5.3(2) ?
N1 C7 C12 C11 . . . . 179.85(12) ?
C8 C7 C12 C11 . . . . 3.05(18) ?
N1 C7 C12 C13 . . . . 5.16(17) ?
C8 C7 C12 C13 . . . . -171.65(11) ?
C6 N2 C13 O1 . . . . 168.01(12) ?
C6 N2 C13 C12 . . . . -16.04(17) ?
C11 C12 C13 O1 . . . . -8.7(2) ?
C7 C12 C13 O1 . . . . 165.83(12) ?
C11 C12 C13 N2 . . . . 175.40(12) ?
C7 C12 C13 N2 . . . . -10.05(17) ?
C9 C8 C14 N3 . . . . -174(3) ?
C7 C8 C14 N3 . . . . 6(3) ?
C10 C9 C16 C17 . . . . -134.73(14) ?
C8 C9 C16 C17 . . . . 43.49(19) ?
C10 C9 C16 C21 . . . . 42.70(18) ?
C8 C9 C16 C21 . . . . -139.07(14) ?
C21 C16 C17 C18 . . . . 0.6(2) ?
C9 C16 C17 C18 . . . . 178.05(13) ?
C16 C17 C18 C19 . . . . -0.3(2) ?
C17 C18 C19 C20 . . . . 0.1(2) ?
C18 C19 C20 C21 . . . . 0.0(3) ?
C19 C20 C21 C16 . . . . 0.3(2) ?
C17 C16 C21 C20 . . . . -0.6(2) ?
C9 C16 C21 C20 . . . . -178.06(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656785
