data_I
loop_
_publ_author_name
'Huan-Mei Guo'
'Fang-Fang Jian'
'Pu-Su Zhao'
'Li-Min Li'
'Qian Wu'
_publ_section_title
;
1-Acetyl-5-(4-chlorophenyl)-3-(4-fluorophenyl)-2-pyrazoline
;
_journal_coeditor_code           AT2246
_journal_issue                   5
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o2620
_journal_page_last               o2621
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C17 H14 Cl F N2 O'
_chemical_formula_moiety         'C17 H14 Cl F N2 O'
_chemical_formula_sum            'C17 H14 Cl F N2 O'
_chemical_formula_weight         316.75
_chemical_melting_point          ?
_chemical_name_common            ?
_chemical_name_systematic
;
1-Acetyl-5-(4-chlorophenyl)-3-(4-fluorophenyl)-2-pyrazoline
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.549(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.119(2)
_cell_length_b                   12.696(5)
_cell_length_c                   19.812(7)
_cell_measurement_reflns_used    2140
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.61
_cell_measurement_theta_min      2.62
_cell_volume                     1525.8(10)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_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  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8612
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         1.91
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.9541
_exptl_absorpt_correction_T_min  0.9251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker,  1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.187
_refine_ls_extinction_coef       0.020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3118
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0677P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1177
_reflns_number_gt                1772
_reflns_number_total             3118
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            cif_filter_013.inp
_cod_data_source_block           I
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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.46496(13) 0.79746(6) 1.05071(3) 0.0924(3) Uani d . 1 . .
F F1 1.0807(2) 1.16308(11) 0.53975(7) 0.0889(5) Uani d . 1 . .
O O1 -0.1341(2) 0.86440(13) 0.75617(7) 0.0690(5) Uani d . 1 . .
N N1 0.3123(3) 0.95275(13) 0.67707(7) 0.0488(4) Uani d . 1 . .
N N2 0.1687(3) 0.93816(13) 0.72473(8) 0.0523(4) Uani d . 1 . .
C C1 0.6290(3) 1.01792(17) 0.59328(11) 0.0591(6) Uani d . 1 . .
H H1 0.5370 0.9620 0.5784 0.071 Uiso calc R 1 . .
C C2 0.7878(4) 1.05008(19) 0.55433(11) 0.0666(6) Uani d . 1 . .
H H2 0.8021 1.0175 0.5131 0.080 Uiso calc R 1 . .
C C3 0.9241(3) 1.13142(17) 0.57817(11) 0.0573(6) Uani d . 1 . .
C C4 0.9092(4) 1.18208(16) 0.63748(11) 0.0567(6) Uani d . 1 . .
H H4 1.0054 1.2365 0.6524 0.068 Uiso calc R 1 . .
C C5 0.7459(4) 1.15006(16) 0.67525(10) 0.0542(5) Uani d . 1 . .
H H5 0.7309 1.1848 0.7157 0.065 Uiso calc R 1 . .
C C6 0.6042(3) 1.06763(14) 0.65427(9) 0.0439(5) Uani d . 1 . .
C C7 0.4344(3) 1.03316(15) 0.69482(9) 0.0455(5) Uani d . 1 . .
C C8 0.3831(4) 1.08576(16) 0.75874(10) 0.0603(6) Uani d . 1 . .
H H8A 0.3284 1.1567 0.7495 0.072 Uiso calc R 1 . .
H H8B 0.5124 1.0885 0.7927 0.072 Uiso calc R 1 . .
C C9 0.2040(3) 1.01474(16) 0.78218(9) 0.0546(5) Uani d . 1 . .
H H9 0.0693 1.0557 0.7842 0.066 Uiso calc R 1 . .
C C10 0.2708(3) 0.96009(15) 0.84960(9) 0.0462(5) Uani d . 1 . .
C C11 0.4696(3) 0.90717(16) 0.86257(10) 0.0556(6) Uani d . 1 . .
H H11 0.5636 0.9047 0.8293 0.067 Uiso calc R 1 . .
C C12 0.5300(3) 0.85781(17) 0.92453(11) 0.0607(6) Uani d . 1 . .
H H12 0.6637 0.8222 0.9328 0.073 Uiso calc R 1 . .
C C13 0.3924(4) 0.86164(16) 0.97335(10) 0.0560(6) Uani d . 1 . .
C C14 0.1938(4) 0.91274(17) 0.96180(10) 0.0594(6) Uani d . 1 . .
H H14 0.0996 0.9141 0.9950 0.071 Uiso calc R 1 . .
C C15 0.1358(4) 0.96230(15) 0.89971(10) 0.0547(5) Uani d . 1 . .
H H15 0.0022 0.9979 0.8918 0.066 Uiso calc R 1 . .
C C16 -0.0015(4) 0.86924(17) 0.71540(10) 0.0538(5) Uani d . 1 . .
C C17 -0.0119(4) 0.79917(18) 0.65383(11) 0.0720(7) Uani d . 1 . .
H H17A -0.1343 0.7517 0.6531 0.108 Uiso calc R 1 . .
H H17B 0.1224 0.7595 0.6557 0.108 Uiso calc R 1 . .
H H17C -0.0305 0.8416 0.6134 0.108 Uiso calc R 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.1183(6) 0.0944(5) 0.0577(4) 0.0057(4) -0.0134(4) 0.0154(3)
F1 0.0825(10) 0.0916(10) 0.1008(10) -0.0281(8) 0.0424(8) -0.0127(8)
O1 0.0519(9) 0.0935(12) 0.0635(9) 0.0003(8) 0.0145(8) 0.0197(8)
N1 0.0471(10) 0.0571(11) 0.0429(9) -0.0030(9) 0.0080(7) 0.0010(8)
N2 0.0560(11) 0.0601(11) 0.0424(9) -0.0064(9) 0.0124(8) -0.0005(8)
C1 0.0533(13) 0.0616(14) 0.0633(13) -0.0117(11) 0.0116(11) -0.0147(11)
C2 0.0632(15) 0.0758(15) 0.0644(14) -0.0132(13) 0.0217(12) -0.0195(12)
C3 0.0512(13) 0.0563(13) 0.0674(14) -0.0066(11) 0.0191(11) 0.0036(11)
C4 0.0633(14) 0.0476(12) 0.0582(13) -0.0109(11) 0.0039(11) 0.0018(10)
C5 0.0707(14) 0.0454(12) 0.0452(11) -0.0028(11) 0.0028(10) 0.0005(9)
C6 0.0472(12) 0.0409(11) 0.0426(10) 0.0020(9) 0.0024(9) 0.0020(9)
C7 0.0497(12) 0.0436(11) 0.0419(10) 0.0028(10) 0.0014(9) 0.0012(9)
C8 0.0827(16) 0.0483(12) 0.0515(12) -0.0028(11) 0.0145(11) -0.0008(10)
C9 0.0608(14) 0.0549(13) 0.0497(12) 0.0078(11) 0.0129(10) 0.0007(10)
C10 0.0491(12) 0.0481(12) 0.0425(11) 0.0048(10) 0.0102(9) -0.0054(9)
C11 0.0499(13) 0.0634(14) 0.0563(13) 0.0035(11) 0.0173(10) -0.0014(10)
C12 0.0488(13) 0.0637(14) 0.0674(14) 0.0082(11) -0.0006(11) -0.0018(11)
C13 0.0660(14) 0.0551(13) 0.0448(11) -0.0006(11) -0.0007(11) -0.0031(9)
C14 0.0701(15) 0.0661(14) 0.0448(12) 0.0089(12) 0.0189(11) -0.0045(10)
C15 0.0557(13) 0.0589(13) 0.0512(12) 0.0156(11) 0.0136(10) -0.0038(10)
C16 0.0465(12) 0.0641(14) 0.0491(12) -0.0008(11) -0.0002(10) 0.0149(10)
C17 0.0760(16) 0.0773(16) 0.0598(13) -0.0233(13) -0.0018(12) 0.0014(12)
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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 N2 . . 108.53(16) ?
C16 N2 N1 . . 122.63(17) ?
C16 N2 C9 . . 123.86(18) ?
N1 N2 C9 . . 113.09(15) ?
C2 C1 C6 . . 121.18(19) ?
C2 C1 H1 . . 119.4 ?
C6 C1 H1 . . 119.4 ?
C3 C2 C1 . . 118.1(2) ?
C3 C2 H2 . . 120.9 ?
C1 C2 H2 . . 120.9 ?
C4 C3 F1 . . 118.55(19) ?
C4 C3 C2 . . 123.4(2) ?
F1 C3 C2 . . 118.1(2) ?
C3 C4 C5 . . 117.70(19) ?
C3 C4 H4 . . 121.1 ?
C5 C4 H4 . . 121.1 ?
C4 C5 C6 . . 121.75(19) ?
C4 C5 H5 . . 119.1 ?
C6 C5 H5 . . 119.1 ?
C5 C6 C1 . . 117.88(19) ?
C5 C6 C7 . . 121.51(17) ?
C1 C6 C7 . . 120.61(17) ?
N1 C7 C6 . . 121.12(17) ?
N1 C7 C8 . . 113.89(18) ?
C6 C7 C8 . . 124.99(17) ?
C7 C8 C9 . . 103.33(16) ?
C7 C8 H8A . . 111.1 ?
C9 C8 H8A . . 111.1 ?
C7 C8 H8B . . 111.1 ?
C9 C8 H8B . . 111.1 ?
H8A C8 H8B . . 109.1 ?
N2 C9 C10 . . 111.73(16) ?
N2 C9 C8 . . 100.92(15) ?
C10 C9 C8 . . 114.54(17) ?
N2 C9 H9 . . 109.8 ?
C10 C9 H9 . . 109.8 ?
C8 C9 H9 . . 109.8 ?
C15 C10 C11 . . 118.24(18) ?
C15 C10 C9 . . 120.74(18) ?
C11 C10 C9 . . 121.02(18) ?
C10 C11 C12 . . 120.7(2) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C13 C12 C11 . . 119.6(2) ?
C13 C12 H12 . . 120.2 ?
C11 C12 H12 . . 120.2 ?
C12 C13 C14 . . 121.01(19) ?
C12 C13 Cl1 . . 119.85(17) ?
C14 C13 Cl1 . . 119.11(18) ?
C13 C14 C15 . . 118.8(2) ?
C13 C14 H14 . . 120.6 ?
C15 C14 H14 . . 120.6 ?
C10 C15 C14 . . 121.65(19) ?
C10 C15 H15 . . 119.2 ?
C14 C15 H15 . . 119.2 ?
O1 C16 N2 . . 120.6(2) ?
O1 C16 C17 . . 123.1(2) ?
N2 C16 C17 . . 116.3(2) ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
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
Cl1 C13 . 1.741(2) ?
F1 C3 . 1.361(2) ?
O1 C16 . 1.219(2) ?
N1 C7 . 1.287(2) ?
N1 N2 . 1.384(2) ?
N2 C16 . 1.354(3) ?
N2 C9 . 1.491(2) ?
C1 C2 . 1.380(3) ?
C1 C6 . 1.389(3) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.371(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.353(3) ?
C4 C5 . 1.386(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.388(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.461(3) ?
C7 C8 . 1.501(3) ?
C8 C9 . 1.537(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.513(3) ?
C9 H9 . 0.9800 ?
C10 C15 . 1.373(3) ?
C10 C11 . 1.384(3) ?
C11 C12 . 1.385(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.364(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.370(3) ?
C14 C15 . 1.386(3) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 C17 . 1.504(3) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
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
C4 H4 O1 2_656 0.9303 2.4826 3.306(3) 147.61
C11 H11 O1 1_655 0.9305 2.5469 3.459(3) 166.51
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
C7 N1 N2 C16 . . . . 170.40(17) ?
C7 N1 N2 C9 . . . . -2.4(2) ?
C6 C1 C2 C3 . . . . 1.3(3) ?
C1 C2 C3 C4 . . . . -0.6(3) ?
C1 C2 C3 F1 . . . . 180.0(2) ?
F1 C3 C4 C5 . . . . 178.77(18) ?
C2 C3 C4 C5 . . . . -0.7(3) ?
C3 C4 C5 C6 . . . . 1.3(3) ?
C4 C5 C6 C1 . . . . -0.6(3) ?
C4 C5 C6 C7 . . . . 179.04(18) ?
C2 C1 C6 C5 . . . . -0.7(3) ?
C2 C1 C6 C7 . . . . 179.64(19) ?
N2 N1 C7 C6 . . . . 179.59(15) ?
N2 N1 C7 C8 . . . . -1.0(2) ?
C5 C6 C7 N1 . . . . -175.86(17) ?
C1 C6 C7 N1 . . . . 3.8(3) ?
C5 C6 C7 C8 . . . . 4.8(3) ?
C1 C6 C7 C8 . . . . -175.57(19) ?
N1 C7 C8 C9 . . . . 3.8(2) ?
C6 C7 C8 C9 . . . . -176.84(17) ?
C16 N2 C9 C10 . . . . 69.6(2) ?
N1 N2 C9 C10 . . . . -117.65(18) ?
C16 N2 C9 C8 . . . . -168.22(18) ?
N1 N2 C9 C8 . . . . 4.5(2) ?
C7 C8 C9 N2 . . . . -4.54(19) ?
C7 C8 C9 C10 . . . . 115.63(18) ?
N2 C9 C10 C15 . . . . -114.9(2) ?
C8 C9 C10 C15 . . . . 131.2(2) ?
N2 C9 C10 C11 . . . . 65.5(2) ?
C8 C9 C10 C11 . . . . -48.4(3) ?
C15 C10 C11 C12 . . . . 0.0(3) ?
C9 C10 C11 C12 . . . . 179.66(18) ?
C10 C11 C12 C13 . . . . -0.2(3) ?
C11 C12 C13 C14 . . . . 0.7(3) ?
C11 C12 C13 Cl1 . . . . 178.69(16) ?
C12 C13 C14 C15 . . . . -1.0(3) ?
Cl1 C13 C14 C15 . . . . -179.05(16) ?
C11 C10 C15 C14 . . . . -0.4(3) ?
C9 C10 C15 C14 . . . . 179.98(18) ?
C13 C14 C15 C10 . . . . 0.9(3) ?
N1 N2 C16 O1 . . . . -174.42(17) ?
C9 N2 C16 O1 . . . . -2.4(3) ?
N1 N2 C16 C17 . . . . 7.0(3) ?
C9 N2 C16 C17 . . . . 179.07(17) ?