#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/84/2218467.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_2218467
loop_
_publ_author_name
'Bukhari, Mujahid Hussain'
'Siddiqui, Hamid Latif'
'Chaudhary, Muhammad Ashraf'
'Hussain, Tanvir'
'Parvez, Masood'
_publ_section_title
;
 4-(4-Fluorophenyl)-6-(2-furyl)pyrimidin-2-amine
;
_journal_coeditor_code           LH2621
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o963
_journal_paper_doi               10.1107/S1600536808012294
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C14 H10 F N3 O'
_chemical_formula_moiety         'C14 H10 F N3 O'
_chemical_formula_sum            'C14 H10 F N3 O'
_chemical_formula_weight         255.25
_chemical_melting_point_gt       513
_chemical_melting_point_lt       515
_chemical_name_systematic
;
4-(4-Fluorophenyl)-6-(2-furyl)pyrimidin-2-amine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 97.69(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.629(4)
_cell_length_b                   5.992(3)
_cell_length_c                   16.389(6)
_cell_measurement_reflns_used    4617
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.6
_cell_volume                     1131.7(8)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ'
_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  0.033
_diffrn_reflns_av_sigmaI/netI    0.041
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4617
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.6
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.21
_refine_ls_extinction_coef       0.025(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.064
_refine_ls_R_factor_gt           0.044
_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)+(0.061P)²+0.4P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.110
_refine_ls_wR_factor_ref         0.123
_reflns_number_gt                1935
_reflns_number_total             2567
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2621.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2218467
_cod_database_fobs_code          2218467
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
F F1 1.25524(8) -0.3651(2) 0.33665(7) 0.0417(3) Uani d . 1
N N1 0.78951(10) -0.1133(2) 0.47173(8) 0.0212(3) Uani d . 1
N N2 0.63490(10) 0.1576(2) 0.46105(8) 0.0214(3) Uani d . 1
N N3 0.64102(12) -0.1403(3) 0.55076(8) 0.0260(3) Uani d . 1
H H31 0.5641(17) -0.128(3) 0.5524(11) 0.031 Uiso d . 1
H H32 0.6685(16) -0.273(4) 0.5618(11) 0.031 Uiso d . 1
O O1 0.68164(9) 0.57384(19) 0.30924(7) 0.0252(3) Uani d . 1
C C1 0.94793(12) -0.0974(3) 0.39086(9) 0.0209(3) Uani d . 1
C C2 0.98310(14) -0.3102(3) 0.41767(10) 0.0269(4) Uani d . 1
H H2 0.9353 -0.3948 0.4488 0.032 Uiso calc R 1
C C3 1.08664(14) -0.4012(3) 0.39983(10) 0.0302(4) Uani d . 1
H H3 1.1108 -0.5456 0.4191 0.036 Uiso calc R 1
C C4 1.15313(13) -0.2769(3) 0.35368(10) 0.0282(4) Uani d . 1
C C5 1.12145(14) -0.0680(3) 0.32395(10) 0.0280(4) Uani d . 1
H H5 1.1690 0.0130 0.2915 0.034 Uiso calc R 1
C C6 1.01768(13) 0.0212(3) 0.34272(10) 0.0256(4) Uani d . 1
H H6 0.9939 0.1649 0.3225 0.031 Uiso calc R 1
C C7 0.83900(12) -0.0007(3) 0.41450(9) 0.0203(3) Uani d . 1
C C8 0.79028(13) 0.1937(3) 0.37932(9) 0.0225(3) Uani d . 1
H H8 0.8261 0.2737 0.3395 0.027 Uiso calc R 1
C C9 0.68719(12) 0.2674(3) 0.40437(9) 0.0200(3) Uani d . 1
C C10 0.68960(12) -0.0280(3) 0.49192(9) 0.0208(3) Uani d . 1
C C11 0.62985(12) 0.4679(3) 0.36912(9) 0.0207(3) Uani d . 1
C C12 0.53195(13) 0.5788(3) 0.38160(10) 0.0242(4) Uani d . 1
H H12 0.4803 0.5406 0.4196 0.029 Uiso calc R 1
C C13 0.52194(14) 0.7633(3) 0.32661(10) 0.0279(4) Uani d . 1
H H13 0.4620 0.8722 0.3206 0.033 Uiso calc R 1
C C14 0.61369(14) 0.7542(3) 0.28479(10) 0.0279(4) Uani d . 1
H H14 0.6291 0.8584 0.2440 0.034 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
C7 N1 C10 116.33(13)
C10 N2 C9 115.37(12)
C10 N3 H31 119.2(12)
C10 N3 H32 115.2(12)
H31 N3 H32 114.2(17)
C14 O1 C11 106.44(12)
C2 C1 C6 118.38(14)
C2 C1 C7 119.86(14)
C6 C1 C7 121.76(14)
C3 C2 C1 121.33(16)
C3 C2 H2 119.3
C1 C2 H2 119.3
C4 C3 C2 118.14(16)
C4 C3 H3 120.9
C2 C3 H3 120.9
F1 C4 C3 118.27(16)
F1 C4 C5 118.67(15)
C3 C4 C5 123.06(15)
C4 C5 C6 118.06(15)
C4 C5 H5 121.0
C6 C5 H5 121.0
C5 C6 C1 121.00(16)
C5 C6 H6 119.5
C1 C6 H6 119.5
N1 C7 C8 121.46(14)
N1 C7 C1 116.36(14)
C8 C7 C1 122.18(14)
C7 C8 C9 117.68(14)
C7 C8 H8 121.2
C9 C8 H8 121.2
N2 C9 C8 122.34(14)
N2 C9 C11 116.84(13)
C8 C9 C11 120.82(14)
N2 C10 N1 126.82(14)
N2 C10 N3 117.09(13)
N1 C10 N3 116.08(14)
C12 C11 O1 109.78(14)
C12 C11 C9 133.89(15)
O1 C11 C9 116.32(13)
C11 C12 C13 106.53(15)
C11 C12 H12 126.7
C13 C12 H12 126.7
C14 C13 C12 106.75(14)
C14 C13 H13 126.6
C12 C13 H13 126.6
C13 C14 O1 110.49(14)
C13 C14 H14 124.8
O1 C14 H14 124.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C4 1.3623(18)
N1 C7 1.346(2)
N1 C10 1.3503(19)
N2 C10 1.346(2)
N2 C9 1.348(2)
N3 C10 1.359(2)
N3 H31 0.902(19)
N3 H32 0.87(2)
O1 C14 1.3667(19)
O1 C11 1.3736(18)
C1 C2 1.392(2)
C1 C6 1.399(2)
C1 C7 1.491(2)
C2 C3 1.388(2)
C2 H2 0.9500
C3 C4 1.372(2)
C3 H3 0.9500
C4 C5 1.376(3)
C5 C6 1.391(2)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.387(2)
C8 C9 1.390(2)
C8 H8 0.9500
C9 C11 1.456(2)
C11 C12 1.357(2)
C12 C13 1.421(2)
C12 H12 0.9500
C13 C14 1.344(2)
C13 H13 0.9500
C14 H14 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
N3 H31 N2 3_656 0.90(2) 2.30(2) 3.190(2) 168(2)
C5 H5 O1 2_745 0.95 2.58 3.474(2) 157
C2 H2 N1 . 0.95 2.46 2.789(2) 100
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
C6 C1 C2 C3 2.2(2)
C7 C1 C2 C3 -177.11(14)
C1 C2 C3 C4 -1.0(2)
C2 C3 C4 F1 179.47(14)
C2 C3 C4 C5 -0.5(2)
F1 C4 C5 C6 -179.16(14)
C3 C4 C5 C6 0.8(2)
C4 C5 C6 C1 0.4(2)
C2 C1 C6 C5 -1.8(2)
C7 C1 C6 C5 177.43(14)
C10 N1 C7 C8 0.8(2)
C10 N1 C7 C1 -178.73(12)
C2 C1 C7 N1 10.0(2)
C6 C1 C7 N1 -169.28(13)
C2 C1 C7 C8 -169.55(14)
C6 C1 C7 C8 11.2(2)
N1 C7 C8 C9 -0.9(2)
C1 C7 C8 C9 178.66(13)
C10 N2 C9 C8 0.2(2)
C10 N2 C9 C11 179.48(13)
C7 C8 C9 N2 0.3(2)
C7 C8 C9 C11 -178.93(13)
C9 N2 C10 N1 -0.3(2)
C9 N2 C10 N3 178.41(13)
C7 N1 C10 N2 -0.3(2)
C7 N1 C10 N3 -178.93(13)
C14 O1 C11 C12 0.17(17)
C14 O1 C11 C9 179.54(13)
N2 C9 C11 C12 1.5(2)
C8 C9 C11 C12 -179.20(16)
N2 C9 C11 O1 -177.67(13)
C8 C9 C11 O1 1.6(2)
O1 C11 C12 C13 0.07(17)
C9 C11 C12 C13 -179.15(16)
C11 C12 C13 C14 -0.29(18)
C12 C13 C14 O1 0.40(18)
C11 O1 C14 C13 -0.36(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24739992
