#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/59/2015998.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_2015998
loop_
_publ_author_name
'Patel, Urmila H.'
'Patel, Pinal D.'
'Thakker, Neha '
_publ_section_title
;C---H···O hydrogen-bonding and
 C---H···π interactions in
 3-(4-fluorophenyl)-1,5,7-trimethyl-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine-2,4-dione
;
_journal_coeditor_code           LN3041
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o337
_journal_page_last               o339
_journal_paper_doi               10.1107/S0108270107017155
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C16 H14 F N3 O2'
_chemical_formula_moiety         'C16 H14 F N3 O2'
_chemical_formula_sum            'C16 H14 F N3 O2'
_chemical_formula_weight         299.30
_chemical_melting_point          483
_chemical_name_systematic
;
3-(4-fluorophenyl)-1,5,7-trimethyl-1,2,3,4-
tetrahydropyrido[2,3-d]pyrimidine-2,4-dione
;
_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
_cell_angle_alpha                97.53(3)
_cell_angle_beta                 97.09(3)
_cell_angle_gamma                93.96(5)
_cell_formula_units_Z            2
_cell_length_a                   7.358(7)
_cell_length_b                   9.377(3)
_cell_length_c                   10.758(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      10
_cell_volume                     727.5(8)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 in WinGX (Farrugia, 1999)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0101
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2776
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_correction_T_min  0.9549
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      1.354
_exptl_crystal_density_method    'floation method'
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.286
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0535
_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)+(0.1004P)²+0.1095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1671
_reflns_number_gt                1765
_reflns_number_total             2559
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ln3041.cif
_cod_data_source_block           I
_cod_database_code               2015998
_cod_database_fobs_code          2015998
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
F F22 0.7109(4) 0.3222(2) 0.38610(15) 0.1229(8) Uani d . 1
N N1 0.7323(3) -0.18573(19) 1.10379(18) 0.0540(5) Uani d . 1
N N7 0.7673(3) 0.02463(17) 0.79753(16) 0.0491(5) Uani d . 1
N N9 0.7497(2) 0.02478(17) 1.01424(16) 0.0472(5) Uani d . 1
O O13 0.7982(2) -0.17994(16) 0.66763(15) 0.0652(5) Uani d . 1
O O14 0.7549(3) 0.23360(15) 0.92862(15) 0.0666(5) Uani d . 1
C C2 0.7337(3) -0.3302(2) 1.0933(2) 0.0614(6) Uani d . 1
C C3 0.7593(4) -0.4136(2) 0.9821(3) 0.0666(7) Uani d . 1
H H3 0.7637 -0.5128 0.9800 0.080 Uiso calc R 1
C C4 0.7783(3) -0.3527(2) 0.8744(2) 0.0575(6) Uani d . 1
C C5 0.7730(3) -0.2013(2) 0.8825(2) 0.0462(5) Uani d . 1
C C6 0.7814(3) -0.1248(2) 0.7741(2) 0.0486(5) Uani d . 1
C C8 0.7572(3) 0.1032(2) 0.9158(2) 0.0477(5) Uani d . 1
C C10 0.7516(3) -0.1256(2) 1.0002(2) 0.0450(5) Uani d . 1
C C11 0.7040(5) -0.3984(3) 1.2088(3) 0.0862(9) Uani d . 1
H H111 0.7895 -0.3519 1.2796 0.129 Uiso calc R 1
H H112 0.7229 -0.4992 1.1939 0.129 Uiso calc R 1
H H113 0.5807 -0.3877 1.2269 0.129 Uiso calc R 1
C C12 0.8057(5) -0.4474(3) 0.7549(3) 0.0831(9) Uani d . 1
H H121 0.9206 -0.4169 0.7288 0.125 Uiso calc R 1
H H122 0.7071 -0.4397 0.6894 0.125 Uiso calc R 1
H H123 0.8068 -0.5459 0.7703 0.125 Uiso calc R 1
C C15 0.7326(3) 0.1068(2) 1.1378(2) 0.0543(6) Uani d . 1
H H151 0.7666 0.2073 1.1369 0.081 Uiso calc R 1
H H152 0.8123 0.0721 1.2027 0.081 Uiso calc R 1
H H153 0.6077 0.0946 1.1546 0.081 Uiso calc R 1
C C16 0.7561(3) 0.1032(2) 0.6898(2) 0.0525(6) Uani d . 1
C C17 0.9085(4) 0.1354(3) 0.6345(2) 0.0691(7) Uani d . 1
H H17 1.0221 0.1081 0.6666 0.083 Uiso calc R 1
C C18 0.8932(5) 0.2085(3) 0.5309(3) 0.0860(9) Uani d . 1
H H18 0.9954 0.2303 0.4918 0.103 Uiso calc R 1
C C19 0.7255(5) 0.2481(3) 0.4874(2) 0.0805(9) Uani d . 1
C C20 0.5725(5) 0.2173(3) 0.5402(3) 0.0796(8) Uani d . 1
H H20 0.4596 0.2455 0.5078 0.095 Uiso calc R 1
C C21 0.5872(4) 0.1431(3) 0.6428(2) 0.0667(7) Uani d . 1
H H21 0.4837 0.1201 0.6803 0.080 Uiso calc R 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'
F F 0.0171 0.0103 '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
C10 N1 C2 116.88(19) y
C8 N7 C6 125.28(17) y
C8 N7 C16 117.23(16) ?
C6 N7 C16 117.45(17) ?
C8 N9 C10 123.17(18) y
C8 N9 C15 116.29(17) ?
C10 N9 C15 120.50(17) ?
N1 C2 C3 122.4(2) ?
N1 C2 C11 116.7(2) ?
C3 C2 C11 120.9(2) ?
C4 C3 C2 121.2(2) ?
C4 C3 H3 119.4 ?
C2 C3 H3 119.4 ?
C3 C4 C5 117.4(2) ?
C3 C4 C12 119.6(2) ?
C5 C4 C12 123.0(2) ?
C10 C5 C4 117.3(2) ?
C10 C5 C6 119.90(18) ?
C4 C5 C6 122.80(19) ?
O13 C6 N7 119.09(19) ?
O13 C6 C5 125.39(19) ?
N7 C6 C5 115.52(18) ?
O14 C8 N9 122.80(19) ?
O14 C8 N7 120.92(18) ?
N9 C8 N7 116.27(17) ?
N1 C10 N9 115.49(18) y
N1 C10 C5 124.89(18) y
N9 C10 C5 119.63(19) y
C2 C11 H111 109.5 ?
C2 C11 H112 109.5 ?
H111 C11 H112 109.5 ?
C2 C11 H113 109.5 ?
H111 C11 H113 109.5 ?
H112 C11 H113 109.5 ?
C4 C12 H121 109.5 ?
C4 C12 H122 109.5 ?
H121 C12 H122 109.5 ?
C4 C12 H123 109.5 ?
H121 C12 H123 109.5 ?
H122 C12 H123 109.5 ?
N9 C15 H151 109.5 ?
N9 C15 H152 109.5 ?
H151 C15 H152 109.5 ?
N9 C15 H153 109.5 ?
H151 C15 H153 109.5 ?
H152 C15 H153 109.5 ?
C17 C16 C21 120.5(2) ?
C17 C16 N7 121.1(2) ?
C21 C16 N7 118.5(2) ?
C16 C17 C18 119.8(3) ?
C16 C17 H17 120.1 ?
C18 C17 H17 120.1 ?
C19 C18 C17 118.6(3) ?
C19 C18 H18 120.7 ?
C17 C18 H18 120.7 ?
C20 C19 C18 122.8(2) ?
C20 C19 F22 118.6(3) ?
C18 C19 F22 118.5(3) ?
C19 C20 C21 118.7(3) ?
C19 C20 H20 120.7 ?
C21 C20 H20 120.7 ?
C20 C21 C16 119.7(3) ?
C20 C21 H21 120.2 ?
C16 C21 H21 120.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F22 C19 1.364(3) ?
N1 C10 1.332(3) y
N1 C2 1.346(3) y
N7 C8 1.397(3) y
N7 C6 1.404(3) y
N7 C16 1.450(3) y
N9 C8 1.371(3) y
N9 C10 1.399(3) y
N9 C15 1.470(3) y
O13 C6 1.218(3) ?
O14 C8 1.214(2) ?
C2 C3 1.382(3) ?
C2 C11 1.503(3) ?
C3 C4 1.375(4) ?
C3 H3 0.9300 ?
C4 C5 1.414(3) ?
C4 C12 1.508(3) ?
C5 C10 1.400(3) ?
C5 C6 1.452(3) ?
C11 H111 0.9600 ?
C11 H112 0.9600 ?
C11 H113 0.9600 ?
C12 H121 0.9600 ?
C12 H122 0.9600 ?
C12 H123 0.9600 ?
C15 H151 0.9600 ?
C15 H152 0.9600 ?
C15 H153 0.9600 ?
C16 C17 1.366(4) ?
C16 C21 1.378(4) ?
C17 C18 1.381(3) ?
C17 H17 0.9300 ?
C18 C19 1.358(4) ?
C18 H18 0.9300 ?
C19 C20 1.352(5) ?
C20 C21 1.377(4) ?
C20 H20 0.9300 ?
C21 H21 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
C3 H3 O14 1_545 0.93 2.36 3.280(4) 168 yes
C18 H18 O13 2_756 0.93 2.45 3.305(5) 153 yes
C20 H20 O13 2_656 0.93 2.49 3.274(5) 142 yes
C15 H153 Cg1 2_657 0.96 2.71 3.617(4) 158 yes
C12 H123 Cg2 1_545 0.96 3.00 3.716(5) 133 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
C10 N1 C2 C3 1.9(4) ?
C10 N1 C2 C11 -177.6(2) ?
N1 C2 C3 C4 -2.3(4) ?
C11 C2 C3 C4 177.1(2) y
C2 C3 C4 C5 0.7(4) ?
C2 C3 C4 C12 -179.9(2) ?
C3 C4 C5 C10 1.0(3) ?
C12 C4 C5 C10 -178.3(2) y
C3 C4 C5 C6 -176.5(2) ?
C12 C4 C5 C6 4.1(4) ?
C8 N7 C6 O13 -176.4(2) y
C16 N7 C6 O13 5.8(3) ?
C8 N7 C6 C5 4.0(3) ?
C16 N7 C6 C5 -173.85(18) y
C10 C5 C6 O13 -179.4(2) ?
C4 C5 C6 O13 -1.9(4) ?
C10 C5 C6 N7 0.2(3) ?
C4 C5 C6 N7 177.66(19) ?
C10 N9 C8 O14 179.8(2) ?
C15 N9 C8 O14 1.9(3) y
C10 N9 C8 N7 -0.1(3) ?
C15 N9 C8 N7 -177.94(18) y
C6 N7 C8 O14 176.1(2) ?
C16 N7 C8 O14 -6.1(3) ?
C6 N7 C8 N9 -4.0(3) ?
C16 N7 C8 N9 173.76(19) ?
C2 N1 C10 N9 -179.98(19) ?
C2 N1 C10 C5 0.0(3) ?
C8 N9 C10 N1 -176.10(19) ?
C15 N9 C10 N1 1.7(3) ?
C8 N9 C10 C5 3.9(3) ?
C15 N9 C10 C5 -178.32(19) ?
C4 C5 C10 N1 -1.5(3) ?
C6 C5 C10 N1 176.16(19) y
C4 C5 C10 N9 178.52(18) y
C6 C5 C10 N9 -3.8(3) ?
C8 N7 C16 C17 105.8(3) y
C6 N7 C16 C17 -76.2(3) ?
C8 N7 C16 C21 -75.1(3) ?
C6 N7 C16 C21 102.9(2) y
C21 C16 C17 C18 0.0(4) ?
N7 C16 C17 C18 179.1(2) ?
C16 C17 C18 C19 0.7(4) ?
C17 C18 C19 C20 -0.9(5) ?
C17 C18 C19 F22 179.1(2) ?
C18 C19 C20 C21 0.3(4) ?
F22 C19 C20 C21 -179.7(2) ?
C19 C20 C21 C16 0.5(4) ?
C17 C16 C21 C20 -0.6(4) ?
N7 C16 C21 C20 -179.7(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133177
