#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/91/2229127.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_2229127
loop_
_publ_author_name
'Han, Zhe'
'Zheng, Hong-Liang'
'Tian, Xue-Lei'
_publ_section_title
;
 Ethyl 1-benzyl-3-(4-fluorophenyl)-1H-pyrazole-5-carboxylate
;
_journal_coeditor_code           JH2256
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o511
_journal_paper_doi               10.1107/S1600536811002340
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H17 F N2 O2'
_chemical_formula_moiety         'C19 H17 F N2 O2'
_chemical_formula_sum            'C19 H17 F N2 O2'
_chemical_formula_weight         324.35
_chemical_name_systematic
;
Ethyl 1-benzyl-3-(4-fluorophenyl)-1H-pyrazole-5-carboxylate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.672(15)
_cell_angle_beta                 102.567(16)
_cell_angle_gamma                91.460(16)
_cell_formula_units_Z            2
_cell_length_a                   8.119(8)
_cell_length_b                   10.173(6)
_cell_length_c                   10.814(6)
_cell_measurement_reflns_used    1645
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      2.41
_cell_volume                     821.5(11)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker SMART CD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4034
_diffrn_reflns_theta_full        13.50
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9888
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.304
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0840
_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)+(0.1650P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2326
_refine_ls_wR_factor_ref         0.2451
_reflns_number_gt                2014
_reflns_number_total             2844
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jh2256.cif
_cod_data_source_block           I
_cod_original_cell_volume        821.5(10)
_cod_database_code               2229127
_cod_database_fobs_code          2229127
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
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.0446(3) 0.7940(3) 1.0242(2) 0.0941(8) Uani d . 1 . .
O O1 0.3457(3) 0.4182(3) 0.1271(2) 0.0856(8) Uani d . 1 . .
O O2 0.3605(2) 0.2792(2) 0.2513(2) 0.0633(6) Uani d . 1 . .
N N1 0.2763(3) 0.6363(2) 0.3527(2) 0.0524(6) Uani d . 1 . .
N N2 0.2347(3) 0.7094(3) 0.4667(2) 0.0544(6) Uani d . 1 . .
C C1 0.0891(4) 0.7506(4) 0.9042(3) 0.0659(9) Uani d . 1 . .
C C2 0.1320(4) 0.6187(4) 0.8574(3) 0.0681(9) Uani d . 1 . .
H H2 0.1317 0.5585 0.9063 0.082 Uiso calc R 1 . .
C C3 0.1762(4) 0.5763(3) 0.7355(3) 0.0604(8) Uani d . 1 . .
H H3 0.2066 0.4865 0.7023 0.072 Uiso calc R 1 . .
C C4 0.1760(3) 0.6651(3) 0.6618(3) 0.0486(7) Uani d . 1 . .
C C5 0.1315(4) 0.7985(3) 0.7127(3) 0.0620(8) Uani d . 1 . .
H H5 0.1308 0.8594 0.6642 0.074 Uiso calc R 1 . .
C C6 0.0878(4) 0.8422(4) 0.8360(3) 0.0694(9) Uani d . 1 . .
H H6 0.0584 0.9321 0.8710 0.083 Uiso calc R 1 . .
C C7 0.2232(3) 0.6190(3) 0.5320(3) 0.0476(7) Uani d . 1 . .
C C8 0.2607(3) 0.4883(3) 0.4600(3) 0.0507(7) Uani d . 1 . .
H H8 0.2623 0.4084 0.4842 0.061 Uiso calc R 1 . .
C C9 0.2947(3) 0.5017(3) 0.3453(3) 0.0496(7) Uani d . 1 . .
C C10 0.3367(3) 0.3994(3) 0.2303(3) 0.0560(8) Uani d . 1 . .
C C11 0.3982(4) 0.1676(3) 0.1414(3) 0.0707(9) Uani d . 1 . .
H H11A 0.5020 0.1943 0.1210 0.085 Uiso calc R 1 . .
H H11B 0.3066 0.1471 0.0614 0.085 Uiso calc R 1 . .
C C12 0.4175(5) 0.0438(4) 0.1851(4) 0.0898(12) Uani d . 1 . .
H H12A 0.5120 0.0638 0.2615 0.135 Uiso calc R 1 . .
H H12B 0.4370 -0.0338 0.1131 0.135 Uiso calc R 1 . .
H H12C 0.3160 0.0211 0.2091 0.135 Uiso calc R 1 . .
C C13 0.3159(3) 0.7111(3) 0.2662(3) 0.0595(8) Uani d . 1 . .
H H13A 0.2573 0.7947 0.2804 0.071 Uiso calc R 1 . .
H H13B 0.2741 0.6528 0.1730 0.071 Uiso calc R 1 . .
C C14 0.5029(3) 0.7517(3) 0.2919(3) 0.0532(7) Uani d . 1 . .
C C15 0.5833(4) 0.7185(3) 0.1874(3) 0.0629(8) Uani d . 1 . .
H H15 0.5221 0.6684 0.1006 0.075 Uiso calc R 1 . .
C C16 0.7528(5) 0.7588(4) 0.2109(5) 0.0802(11) Uani d . 1 . .
H H16 0.8057 0.7374 0.1397 0.096 Uiso calc R 1 . .
C C17 0.8439(4) 0.8301(4) 0.3378(5) 0.0899(13) Uani d . 1 . .
H H17 0.9591 0.8567 0.3533 0.108 Uiso calc R 1 . .
C C18 0.7659(5) 0.8628(4) 0.4434(5) 0.0916(12) Uani d . 1 . .
H H18 0.8287 0.9107 0.5302 0.110 Uiso calc R 1 . .
C C19 0.5959(4) 0.8248(4) 0.4209(3) 0.0698(9) Uani d . 1 . .
H H19 0.5431 0.8480 0.4921 0.084 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 O2 C11 . . 116.1(3) ?
N2 N1 C9 . . 111.5(2) ?
N2 N1 C13 . . 118.3(2) ?
C9 N1 C13 . . 129.6(2) ?
C7 N2 N1 . . 105.6(2) ?
C2 C1 C6 . . 122.8(3) ?
C2 C1 F1 . . 119.1(3) ?
C6 C1 F1 . . 118.1(3) ?
C1 C2 C3 . . 118.4(3) ?
C1 C2 H2 . . 120.8 ?
C3 C2 H2 . . 120.8 ?
C2 C3 C4 . . 121.1(3) ?
C2 C3 H3 . . 119.5 ?
C4 C3 H3 . . 119.5 ?
C5 C4 C3 . . 118.9(3) ?
C5 C4 C7 . . 120.4(3) ?
C3 C4 C7 . . 120.7(3) ?
C4 C5 C6 . . 120.3(3) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C1 C6 C5 . . 118.5(3) ?
C1 C6 H6 . . 120.7 ?
C5 C6 H6 . . 120.7 ?
N2 C7 C8 . . 110.7(2) ?
N2 C7 C4 . . 119.9(2) ?
C8 C7 C4 . . 129.3(3) ?
C9 C8 C7 . . 105.6(3) ?
C9 C8 H8 . . 127.2 ?
C7 C8 H8 . . 127.2 ?
N1 C9 C8 . . 106.6(2) ?
N1 C9 C10 . . 122.5(3) ?
C8 C9 C10 . . 130.9(3) ?
O1 C10 O2 . . 123.3(3) ?
O1 C10 C9 . . 125.5(3) ?
O2 C10 C9 . . 111.1(3) ?
O2 C11 C12 . . 107.1(3) ?
O2 C11 H11A . . 110.3 ?
C12 C11 H11A . . 110.3 ?
O2 C11 H11B . . 110.3 ?
C12 C11 H11B . . 110.3 ?
H11A C11 H11B . . 108.5 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N1 C13 C14 . . 112.9(2) ?
N1 C13 H13A . . 109.0 ?
C14 C13 H13A . . 109.0 ?
N1 C13 H13B . . 109.0 ?
C14 C13 H13B . . 109.0 ?
H13A C13 H13B . . 107.8 ?
C15 C14 C19 . . 119.2(3) ?
C15 C14 C13 . . 120.6(3) ?
C19 C14 C13 . . 120.1(3) ?
C16 C15 C14 . . 120.3(3) ?
C16 C15 H15 . . 119.8 ?
C14 C15 H15 . . 119.8 ?
C17 C16 C15 . . 120.3(3) ?
C17 C16 H16 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
C16 C17 C18 . . 120.1(3) ?
C16 C17 H17 . . 120.0 ?
C18 C17 H17 . . 120.0 ?
C19 C18 C17 . . 120.2(4) ?
C19 C18 H18 . . 119.9 ?
C17 C18 H18 . . 119.9 ?
C18 C19 C14 . . 119.9(3) ?
C18 C19 H19 . . 120.1 ?
C14 C19 H19 . . 120.1 ?
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
F1 C1 . 1.362(4) ?
O1 C10 . 1.208(4) ?
O2 C10 . 1.325(4) ?
O2 C11 . 1.451(4) ?
N1 N2 . 1.340(3) ?
N1 C9 . 1.360(4) ?
N1 C13 . 1.460(3) ?
N2 C7 . 1.339(3) ?
C1 C2 . 1.358(5) ?
C1 C6 . 1.360(5) ?
C2 C3 . 1.379(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.382(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.382(4) ?
C4 C7 . 1.470(4) ?
C5 C6 . 1.392(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.388(4) ?
C8 C9 . 1.374(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.456(4) ?
C11 C12 . 1.480(5) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C14 . 1.504(4) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.380(4) ?
C14 C19 . 1.385(4) ?
C15 C16 . 1.371(5) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.360(6) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.378(6) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.372(5) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
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
C9 N1 N2 C7 . . . . -1.2(3) ?
C13 N1 N2 C7 . . . . -173.5(2) ?
C6 C1 C2 C3 . . . . 0.0(5) ?
F1 C1 C2 C3 . . . . 179.8(3) ?
C1 C2 C3 C4 . . . . -0.4(5) ?
C2 C3 C4 C5 . . . . 0.4(4) ?
C2 C3 C4 C7 . . . . 180.0(3) ?
C3 C4 C5 C6 . . . . 0.0(4) ?
C7 C4 C5 C6 . . . . -179.6(2) ?
C2 C1 C6 C5 . . . . 0.4(5) ?
F1 C1 C6 C5 . . . . -179.4(3) ?
C4 C5 C6 C1 . . . . -0.4(5) ?
N1 N2 C7 C8 . . . . 1.0(3) ?
N1 N2 C7 C4 . . . . -178.9(2) ?
C5 C4 C7 N2 . . . . 4.6(4) ?
C3 C4 C7 N2 . . . . -175.0(2) ?
C5 C4 C7 C8 . . . . -175.3(3) ?
C3 C4 C7 C8 . . . . 5.0(4) ?
N2 C7 C8 C9 . . . . -0.5(3) ?
C4 C7 C8 C9 . . . . 179.4(2) ?
N2 N1 C9 C8 . . . . 0.8(3) ?
C13 N1 C9 C8 . . . . 172.1(3) ?
N2 N1 C9 C10 . . . . 178.8(2) ?
C13 N1 C9 C10 . . . . -9.9(4) ?
C7 C8 C9 N1 . . . . -0.2(3) ?
C7 C8 C9 C10 . . . . -177.9(3) ?
C11 O2 C10 O1 . . . . -0.3(4) ?
C11 O2 C10 C9 . . . . 178.2(2) ?
N1 C9 C10 O1 . . . . -6.4(4) ?
C8 C9 C10 O1 . . . . 171.0(3) ?
N1 C9 C10 O2 . . . . 175.1(2) ?
C8 C9 C10 O2 . . . . -7.4(4) ?
C10 O2 C11 C12 . . . . -179.2(3) ?
N2 N1 C13 C14 . . . . 94.7(3) ?
C9 N1 C13 C14 . . . . -76.1(4) ?
N1 C13 C14 C15 . . . . 128.1(3) ?
N1 C13 C14 C19 . . . . -52.8(4) ?
C19 C14 C15 C16 . . . . -0.8(4) ?
C13 C14 C15 C16 . . . . 178.3(3) ?
C14 C15 C16 C17 . . . . 1.1(5) ?
C15 C16 C17 C18 . . . . -0.4(6) ?
C16 C17 C18 C19 . . . . -0.6(6) ?
C17 C18 C19 C14 . . . . 0.9(6) ?
C15 C14 C19 C18 . . . . -0.2(5) ?
C13 C14 C19 C18 . . . . -179.3(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21498827
