#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/51/2235133.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_2235133
loop_
_publ_author_name
'Wen, Qin-Mei'
'Yin, Ben-Tao'
'Yan, Cong-Yan'
'Zhou, Cheng-He'
_publ_section_title
;
 (Z)-1-[4-Fluoro-2-(pyrrolidin-1-yl)phenyl]-3-phenyl-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one
;
_journal_coeditor_code           LH5432
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1642
_journal_paper_doi               10.1107/S1600536812018454
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C21 H19 F N4 O'
_chemical_formula_moiety         'C21 H19 F N4 O'
_chemical_formula_sum            'C21 H19 F N4 O'
_chemical_formula_weight         362.40
_chemical_name_systematic
;
(Z)-1-[4-Fluoro-2-(pyrrolidin-1-yl)phenyl]-3-phenyl-
2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.47(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.217(2)
_cell_length_b                   10.067(2)
_cell_length_c                   15.793(3)
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.737
_cell_measurement_theta_min      2.250
_cell_volume                     1777.9(6)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0582
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13447
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9972
_exptl_absorpt_correction_T_min  0.9725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.188
_refine_ls_extinction_coef       0.0075(13)
_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   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         3403
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0478
_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)+(0.0576P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1184
_reflns_number_gt                2341
_reflns_number_total             3403
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5432.cif
_cod_data_source_block           I
_cod_original_cell_volume        1778.0(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235133
_cod_database_fobs_code          2235133
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
_atom_site_symmetry_multiplicity
F F1 0.06331(9) 0.07121(12) 0.14879(7) 0.0506(4) Uani d . 1 1
N N3 0.73647(12) -0.01216(15) 0.27605(9) 0.0291(4) Uani d . 1 1
O O1 0.54633(11) 0.01888(14) 0.36550(8) 0.0389(4) Uani d . 1 1
C C8 0.62355(15) -0.06156(19) 0.24237(11) 0.0289(4) Uani d D 1 1
C C16 0.18387(18) -0.0239(2) 0.25987(13) 0.0340(5) Uani d . 1 1
C C17 0.29747(16) -0.06191(18) 0.29689(11) 0.0290(4) Uani d . 1 1
C C12 0.39893(16) -0.02771(18) 0.25277(11) 0.0290(4) Uani d . 1 1
N N2 0.76525(14) 0.11901(16) 0.27051(10) 0.0378(4) Uani d . 1 1
N N4 0.30375(13) -0.13062(16) 0.37147(9) 0.0320(4) Uani d . 1 1
C C13 0.38080(18) 0.02722(19) 0.17088(12) 0.0336(5) Uani d . 1 1
C C6 0.70879(16) -0.19160(19) 0.12221(11) 0.0291(4) Uani d . 1 1
C C11 0.52247(16) -0.02255(19) 0.29265(12) 0.0306(5) Uani d . 1 1
C C7 0.61641(17) -0.14582(19) 0.17621(11) 0.0312(5) Uani d . 1 1
C C3 0.87605(18) -0.2952(2) 0.01763(12) 0.0369(5) Uani d D 1 1
N N1 0.91459(14) 0.00330(19) 0.34166(10) 0.0422(5) Uani d . 1 1
C C5 0.68283(18) -0.3030(2) 0.07170(11) 0.0324(5) Uani d . 1 1
C C2 0.90214(18) -0.1816(2) 0.06478(12) 0.0369(5) Uani d D 1 1
C C1 0.82010(17) -0.1292(2) 0.11679(12) 0.0330(5) Uani d D 1 1
C C15 0.17490(16) 0.0344(2) 0.18190(13) 0.0363(5) Uani d . 1 1
C C18 0.19584(18) -0.1755(2) 0.41003(13) 0.0387(5) Uani d . 1 1
C C10 0.82587(17) -0.0775(2) 0.31872(12) 0.0354(5) Uani d . 1 1
C C9 0.87283(19) 0.1214(2) 0.31018(13) 0.0406(5) Uani d . 1 1
C C14 0.26982(18) 0.0594(2) 0.13393(14) 0.0365(5) Uani d . 1 1
C C4 0.76540(19) -0.3541(2) 0.01975(12) 0.0365(5) Uani d . 1 1
C C21 0.40905(18) -0.2063(2) 0.40537(14) 0.0392(5) Uani d . 1 1
C C20 0.3575(2) -0.3164(2) 0.45719(15) 0.0446(6) Uani d . 1 1
C C19 0.2455(2) -0.2535(3) 0.48764(15) 0.0477(6) Uani d . 1 1
H H15 0.5351(16) -0.1852(18) 0.1620(10) 0.031(5) Uiso d . 1 1
H H23 0.1166(17) -0.0388(19) 0.2867(12) 0.038(6) Uiso d . 1 1
H H3A 0.4540(15) -0.2398(18) 0.3554(11) 0.037(5) Uiso d . 1 1
H H5 0.2578(17) 0.1005(19) 0.0796(12) 0.042(6) Uiso d . 1 1
H H12 0.6041(17) -0.3451(19) 0.0728(11) 0.036(5) Uiso d . 1 1
H H7 0.8209(17) -0.174(2) 0.3276(12) 0.044(6) Uiso d . 1 1
H H8A 0.1441(17) -0.096(2) 0.4266(11) 0.043(6) Uiso d . 1 1
H H2A 0.3393(17) -0.396(2) 0.4217(12) 0.044(6) Uiso d . 1 1
H H18 0.4500(16) 0.0451(18) 0.1429(12) 0.037(5) Uiso d . 1 1
H H6 0.9173(18) 0.205(2) 0.3160(12) 0.048(6) Uiso d . 1 1
H H4 0.7450(17) -0.432(2) -0.0150(12) 0.041(6) Uiso d . 1 1
H H14 0.9352(18) -0.332(2) -0.0180(11) 0.047(6) Uiso d . 1 1
H H11 0.9777(18) -0.1339(19) 0.0632(11) 0.039(5) Uiso d . 1 1
H H8B 0.1457(18) -0.2321(19) 0.3678(12) 0.046(6) Uiso d . 1 1
H H10 0.8385(17) -0.0451(19) 0.1478(12) 0.044(6) Uiso d . 1 1
H H3B 0.4656(19) -0.144(2) 0.4417(13) 0.057(7) Uiso d . 1 1
H H1A 0.1847(19) -0.322(2) 0.5052(13) 0.060(7) Uiso d . 1 1
H H2B 0.4184(19) -0.346(2) 0.5040(12) 0.049(6) Uiso d . 1 1
H H1B 0.267(2) -0.193(2) 0.5352(14) 0.068(8) 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'
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
C10 N3 N2 109.69(16)
C10 N3 C8 128.79(17)
N2 N3 C8 121.47(15)
C7 C8 N3 120.55(16)
C7 C8 C11 125.48(17)
N3 C8 C11 113.65(15)
C15 C16 C17 119.48(19)
C15 C16 H23 119.3(12)
C17 C16 H23 121.2(12)
N4 C17 C16 118.64(16)
N4 C17 C12 123.83(16)
C16 C17 C12 117.52(17)
C13 C12 C17 118.80(17)
C13 C12 C11 116.20(16)
C17 C12 C11 124.01(16)
C9 N2 N3 101.55(17)
C17 N4 C18 121.73(16)
C17 N4 C21 124.29(15)
C18 N4 C21 110.76(15)
C14 C13 C12 123.04(19)
C14 C13 H18 120.7(11)
C12 C13 H18 116.2(11)
C5 C6 C1 118.15(17)
C5 C6 C7 117.39(17)
C1 C6 C7 124.45(18)
O1 C11 C12 122.52(16)
O1 C11 C8 117.93(16)
C12 C11 C8 119.47(16)
C8 C7 C6 130.44(18)
C8 C7 H15 114.9(10)
C6 C7 H15 114.6(10)
C4 C3 C2 119.69(19)
C4 C3 H14 120.5(12)
C2 C3 H14 119.8(12)
C10 N1 C9 102.06(18)
C4 C5 C6 121.24(19)
C4 C5 H12 119.7(11)
C6 C5 H12 119.1(11)
C3 C2 C1 120.8(2)
C3 C2 H11 122.7(11)
C1 C2 H11 116.5(12)
C2 C1 C6 120.0(2)
C2 C1 H10 119.7(11)
C6 C1 H10 120.2(11)
C16 C15 F1 117.59(17)
C16 C15 C14 124.80(18)
F1 C15 C14 117.60(17)
N4 C18 C19 103.35(17)
N4 C18 H8A 111.4(10)
C19 C18 H8A 111.9(10)
N4 C18 H8B 109.5(11)
C19 C18 H8B 112.8(11)
H8A C18 H8B 107.9(15)
N1 C10 N3 110.9(2)
N1 C10 H7 128.5(12)
N3 C10 H7 120.6(12)
N2 C9 N1 115.8(2)
N2 C9 H6 120.1(12)
N1 C9 H6 124.1(12)
C13 C14 C15 115.96(19)
C13 C14 H5 123.1(12)
C15 C14 H5 120.9(12)
C3 C4 C5 120.1(2)
C3 C4 H4 120.3(11)
C5 C4 H4 119.6(11)
N4 C21 C20 104.23(17)
N4 C21 H3A 108.6(10)
C20 C21 H3A 113.9(10)
N4 C21 H3B 109.3(12)
C20 C21 H3B 112.6(12)
H3A C21 H3B 108.0(15)
C21 C20 C19 103.03(19)
C21 C20 H2A 110.8(11)
C19 C20 H2A 112.1(12)
C21 C20 H2B 110.3(12)
C19 C20 H2B 114.9(12)
H2A C20 H2B 105.9(17)
C20 C19 C18 102.69(18)
C20 C19 H1A 112.8(12)
C18 C19 H1A 110.9(12)
C20 C19 H1B 110.2(14)
C18 C19 H1B 110.3(14)
H1A C19 H1B 109.8(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C15 1.370(2)
N3 C10 1.337(2)
N3 N2 1.364(2)
N3 C8 1.425(2)
O1 C11 1.233(2)
C8 C7 1.343(3)
C8 C11 1.487(2)
C16 C15 1.361(3)
C16 C17 1.413(3)
C16 H23 0.906(19)
C17 N4 1.363(2)
C17 C12 1.422(2)
C12 C13 1.407(3)
C12 C11 1.478(3)
N2 C9 1.316(3)
N4 C18 1.468(2)
N4 C21 1.471(2)
C13 C14 1.372(3)
C13 H18 0.940(19)
C6 C5 1.394(3)
C6 C1 1.406(3)
C6 C7 1.467(2)
C7 H15 1.004(18)
C3 C4 1.378(3)
C3 C2 1.384(3)
C3 H14 0.974(19)
N1 C10 1.314(3)
N1 C9 1.358(3)
C5 C4 1.383(3)
C5 H12 0.980(19)
C2 C1 1.385(3)
C2 H11 0.976(19)
C1 H10 0.99(2)
C15 C14 1.377(3)
C18 C19 1.524(3)
C18 H8A 1.03(2)
C18 H8B 1.01(2)
C10 H7 0.98(2)
C9 H6 0.98(2)
C14 H5 0.954(19)
C4 H4 0.98(2)
C21 C20 1.519(3)
C21 H3A 1.026(18)
C21 H3B 1.03(2)
C20 C19 1.519(3)
C20 H2A 0.99(2)
C20 H2B 1.01(2)
C19 H1A 1.03(2)
C19 H1B 0.98(2)
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
C5 H12 O1 2_645 0.981(19) 2.435(19) 3.347(2) 154.6(14)
C16 H23 N1 1_455 0.906(19) 2.525(19) 3.388(3) 159.3(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657789
