#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/78/2227809.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227809
loop_
_publ_author_name
'Shi, Daxin'
'Yang, Liupan'
'Tang, Jianhong'
'Wang, Xiuzhen'
'Li, Jiarong'
_publ_section_title
;
 Spiro[cyclopentane-1,2'(1'H)-pyrido[2,3-d]pyrimidin]-4'(3'H)-one
;
_journal_coeditor_code           LX2156
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2301
_journal_paper_doi               10.1107/S1600536810027479
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H13 N3 O'
_chemical_formula_moiety         'C11 H13 N3 O'
_chemical_formula_sum            'C11 H13 N3 O'
_chemical_formula_weight         203.24
_chemical_name_systematic
;
Spiro[cyclopentane-1,2'(1'H)-pyrido[2,3-d]pyrimidin]-
4'(3'H)-one
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.4000(10)
_cell_length_b                   12.1650(15)
_cell_length_c                   15.370(2)
_cell_measurement_reflns_used    9441
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      35.60
_cell_measurement_theta_min      1.30
_cell_volume                     1944.6(4)
_computing_cell_refinement       'Crystal Clear-SM Expert (Rigaku/MSC, 2009)'
_computing_data_collection       'Crystal Clear-SM Expert (Rigaku/MSC, 2009)'
_computing_data_reduction        'Crystal Clear-SM Expert (Rigaku/MSC, 2009)'
_computing_molecular_graphics    'CrystalStructure (Rigaku/MSC, 2009)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.222
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'graphite  multilayer'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21571
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.65
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9744
_exptl_absorpt_correction_T_min  0.9709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear-SM Expert; Rigaku/MSC, 2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2314
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0395
_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)+(0.0569P)²+0.6834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                2168
_reflns_number_total             2314
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            lx2156.cif
_cod_data_source_block           I
_cod_database_code               2227809
_cod_database_fobs_code          2227809
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -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 0.59391(7) 0.42006(6) 0.57792(5) 0.01563(19) Uani d . 1 . .
N N1 0.94264(9) 0.63850(8) 0.68372(6) 0.0171(2) Uani d . 1 . .
N N2 0.80796(9) 0.69549(8) 0.57226(6) 0.0155(2) Uani d . 1 . .
N N3 0.64694(9) 0.58137(7) 0.51402(6) 0.0146(2) Uani d . 1 . .
C C1 0.84778(10) 0.61467(9) 0.62723(7) 0.0137(2) Uani d . 1 . .
C C2 0.78414(10) 0.51204(9) 0.62574(7) 0.0137(2) Uani d . 1 . .
C C3 0.82323(11) 0.43170(9) 0.68436(7) 0.0164(2) Uani d . 1 . .
H H3 0.7818 0.3621 0.6855 0.020 Uiso calc R 1 . .
C C4 0.92347(11) 0.45420(9) 0.74123(7) 0.0185(2) Uani d . 1 . .
H H4 0.9539 0.4001 0.7808 0.022 Uiso calc R 1 . .
C C5 0.97766(11) 0.55837(9) 0.73836(7) 0.0184(2) Uani d . 1 . .
H H5 1.0449 0.5740 0.7783 0.022 Uiso calc R 1 . .
C C6 0.66943(10) 0.49939(9) 0.57020(7) 0.0130(2) Uani d . 1 . .
C C7 0.74197(10) 0.66576(8) 0.49201(7) 0.0134(2) Uani d . 1 . .
C C8 0.83702(11) 0.62728(9) 0.42121(7) 0.0168(2) Uani d . 1 . .
H H8A 0.9065 0.5818 0.4465 0.020 Uiso calc R 1 . .
H H8B 0.7924 0.5845 0.3755 0.020 Uiso calc R 1 . .
C C9 0.88986(11) 0.73498(9) 0.38493(7) 0.0193(2) Uani d . 1 . .
H H9A 0.9265 0.7242 0.3261 0.023 Uiso calc R 1 . .
H H9B 0.9571 0.7656 0.4235 0.023 Uiso calc R 1 . .
C C10 0.77185(12) 0.81065(10) 0.38176(8) 0.0231(3) Uani d . 1 . .
H H10A 0.7316 0.8083 0.3234 0.028 Uiso calc R 1 . .
H H10B 0.7969 0.8875 0.3947 0.028 Uiso calc R 1 . .
C C11 0.67779(10) 0.76755(9) 0.45118(7) 0.0160(2) Uani d . 1 . .
H H11A 0.5946 0.7474 0.4242 0.019 Uiso calc R 1 . .
H H11B 0.6620 0.8244 0.4960 0.019 Uiso calc R 1 . .
H H1 0.8471(15) 0.7598(14) 0.5750(10) 0.030(4) Uiso d . 1 . .
H H2 0.5769(16) 0.5770(12) 0.4815(10) 0.024(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
C5 N1 C1 . . 116.60(10) ?
C1 N2 C7 . . 119.32(9) ?
C1 N2 H1 . . 118.1(10) ?
C7 N2 H1 . . 118.5(10) ?
C6 N3 C7 . . 123.56(9) ?
C6 N3 H2 . . 117.6(9) ?
C7 N3 H2 . . 117.8(9) ?
N1 C1 N2 . . 117.90(10) ?
N1 C1 C2 . . 122.96(10) ?
N2 C1 C2 . . 119.05(10) ?
C3 C2 C1 . . 118.28(10) ?
C3 C2 C6 . . 122.57(10) ?
C1 C2 C6 . . 118.70(9) ?
C4 C3 C2 . . 119.29(10) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C5 C4 C3 . . 117.72(10) ?
C5 C4 H4 . . 121.1 ?
C3 C4 H4 . . 121.1 ?
N1 C5 C4 . . 125.11(10) ?
N1 C5 H5 . . 117.4 ?
C4 C5 H5 . . 117.4 ?
O1 C6 N3 . . 121.75(10) ?
O1 C6 C2 . . 122.26(10) ?
N3 C6 C2 . . 115.89(9) ?
N2 C7 N3 . . 107.23(8) ?
N2 C7 C11 . . 110.45(9) ?
N3 C7 C11 . . 111.42(9) ?
N2 C7 C8 . . 111.75(9) ?
N3 C7 C8 . . 112.50(9) ?
C11 C7 C8 . . 103.55(8) ?
C9 C8 C7 . . 103.17(9) ?
C9 C8 H8A . . 111.1 ?
C7 C8 H8A . . 111.1 ?
C9 C8 H8B . . 111.1 ?
C7 C8 H8B . . 111.1 ?
H8A C8 H8B . . 109.1 ?
C8 C9 C10 . . 103.80(9) ?
C8 C9 H9A . . 111.0 ?
C10 C9 H9A . . 111.0 ?
C8 C9 H9B . . 111.0 ?
C10 C9 H9B . . 111.0 ?
H9A C9 H9B . . 109.0 ?
C9 C10 C11 . . 106.36(9) ?
C9 C10 H10A . . 110.5 ?
C11 C10 H10A . . 110.5 ?
C9 C10 H10B . . 110.5 ?
C11 C10 H10B . . 110.5 ?
H10A C10 H10B . . 108.6 ?
C10 C11 C7 . . 106.30(9) ?
C10 C11 H11A . . 110.5 ?
C7 C11 H11A . . 110.5 ?
C10 C11 H11B . . 110.5 ?
C7 C11 H11B . . 110.5 ?
H11A C11 H11B . . 108.7 ?
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 C6 . 1.2500(13) ?
N1 C5 . 1.3372(14) ?
N1 C1 . 1.3458(14) ?
N2 C1 . 1.3609(14) ?
N2 C7 . 1.4571(13) ?
N2 H1 . 0.882(17) ?
N3 C6 . 1.3397(14) ?
N3 C7 . 1.4646(13) ?
N3 H2 . 0.885(16) ?
C1 C2 . 1.4132(15) ?
C2 C3 . 1.3900(15) ?
C2 C6 . 1.4750(14) ?
C3 C4 . 1.3878(16) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3876(16) ?
C4 H4 . 0.9500 ?
C5 H5 . 0.9500 ?
C7 C11 . 1.5404(14) ?
C7 C8 . 1.5428(15) ?
C8 C9 . 1.5262(16) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.5349(16) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.5397(15) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 H11A . 0.9900 ?
C11 H11B . 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 H1 O1 2_655 0.88(2) 2.05(2) 2.9180(10) 170(2)
N3 H2 O1 5_666 0.89(2) 2.00(2) 2.8760(10) 172.0(10)
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
C5 N1 C1 N2 . . . . 178.43(10) ?
C5 N1 C1 C2 . . . . 1.72(16) ?
C7 N2 C1 N1 . . . . 158.25(10) ?
C7 N2 C1 C2 . . . . -24.91(15) ?
N1 C1 C2 C3 . . . . -1.20(16) ?
N2 C1 C2 C3 . . . . -177.86(10) ?
N1 C1 C2 C6 . . . . 171.29(10) ?
N2 C1 C2 C6 . . . . -5.38(15) ?
C1 C2 C3 C4 . . . . -0.71(16) ?
C6 C2 C3 C4 . . . . -172.89(10) ?
C2 C3 C4 C5 . . . . 1.92(16) ?
C1 N1 C5 C4 . . . . -0.39(17) ?
C3 C4 C5 N1 . . . . -1.43(17) ?
C7 N3 C6 O1 . . . . -169.27(9) ?
C7 N3 C6 C2 . . . . 14.28(15) ?
C3 C2 C6 O1 . . . . 6.53(16) ?
C1 C2 C6 O1 . . . . -165.62(10) ?
C3 C2 C6 N3 . . . . -177.04(10) ?
C1 C2 C6 N3 . . . . 10.81(14) ?
C1 N2 C7 N3 . . . . 44.94(13) ?
C1 N2 C7 C11 . . . . 166.52(9) ?
C1 N2 C7 C8 . . . . -78.77(12) ?
C6 N3 C7 N2 . . . . -40.32(13) ?
C6 N3 C7 C11 . . . . -161.29(10) ?
C6 N3 C7 C8 . . . . 82.94(12) ?
N2 C7 C8 C9 . . . . -79.95(10) ?
N3 C7 C8 C9 . . . . 159.36(9) ?
C11 C7 C8 C9 . . . . 38.94(10) ?
C7 C8 C9 C10 . . . . -39.83(11) ?
C8 C9 C10 C11 . . . . 25.43(12) ?
C9 C10 C11 C7 . . . . -1.25(12) ?
N2 C7 C11 C10 . . . . 96.69(10) ?
N3 C7 C11 C10 . . . . -144.24(9) ?
C8 C7 C11 C10 . . . . -23.09(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745541
