#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/03/2230321.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_2230321
loop_
_publ_author_name
'Ge, Yan Qing'
'Zhang, Ji Mei'
'Wang, Guang Liang'
'Xu, Hao'
'Shi, Bo'
_publ_section_title
;
 Ethyl
 1-(4-chlorobenzyl)-3-(4-fluorophenyl)-1H-pyrazole-5-carboxylate
;
_journal_coeditor_code           FY2010
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1387
_journal_paper_doi               10.1107/S1600536811017156
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H16 Cl F N2 O2'
_chemical_formula_moiety         'C19 H16 Cl F N2 O2'
_chemical_formula_sum            'C19 H16 Cl F N2 O2'
_chemical_formula_weight         358.79
_chemical_name_systematic
;
Ethyl 1-(4-chlorobenzyl)-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                109.128(7)
_cell_angle_beta                 93.269(7)
_cell_angle_gamma                104.842(7)
_cell_formula_units_Z            2
_cell_length_a                   8.267(4)
_cell_length_b                   10.375(5)
_cell_length_c                   11.368(5)
_cell_measurement_reflns_used    2637
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.33
_cell_volume                     879.8(7)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'SMART (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4589
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_correction_T_min  0.9488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.316
_refine_ls_extinction_coef       0.377(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0415
_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)+(0.0578P)²+0.1997P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                2570
_reflns_number_total             3091
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            fy2010.cif
_cod_data_source_block           I
_cod_database_code               2230321
_cod_database_fobs_code          2230321
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 1.50553(8) 0.97753(7) 0.28534(7) 0.0902(3) Uani d . 1 1 . .
F F1 0.58679(18) 0.70217(16) 1.03659(11) 0.0901(4) Uani d . 1 1 . .
O O1 0.8333(2) 0.38223(15) 0.13974(12) 0.0730(4) Uani d . 1 1 . .
O O2 0.85036(17) 0.24464(14) 0.25387(12) 0.0635(4) Uani d . 1 1 . .
N N1 0.76250(18) 0.58191(16) 0.36486(13) 0.0520(4) Uani d . 1 1 . .
N N2 0.72669(19) 0.64677(16) 0.47978(13) 0.0538(4) Uani d . 1 1 . .
C C1 1.2960(3) 0.8828(2) 0.28289(19) 0.0623(5) Uani d . 1 1 . .
C C2 1.2032(3) 0.7838(2) 0.17127(17) 0.0613(5) Uani d . 1 1 . .
H H2 1.2510 0.7663 0.0976 0.074 Uiso calc R 1 1 . .
C C3 1.0381(3) 0.7106(2) 0.17021(16) 0.0581(5) Uani d . 1 1 . .
H H3 0.9750 0.6430 0.0949 0.070 Uiso calc R 1 1 . .
C C4 0.9639(2) 0.73540(19) 0.27895(15) 0.0530(4) Uani d . 1 1 . .
C C5 1.0613(3) 0.8359(2) 0.39014(17) 0.0665(5) Uani d . 1 1 . .
H H5 1.0142 0.8537 0.4641 0.080 Uiso calc R 1 1 . .
C C6 1.2269(3) 0.9101(2) 0.39306(19) 0.0735(6) Uani d . 1 1 . .
H H6 1.2910 0.9774 0.4681 0.088 Uiso calc R 1 1 . .
C C7 0.7810(2) 0.6583(2) 0.27612(17) 0.0589(5) Uani d . 1 1 . .
H H7A 0.7168 0.7269 0.2968 0.071 Uiso calc R 1 1 . .
H H7B 0.7342 0.5910 0.1916 0.071 Uiso calc R 1 1 . .
C C8 0.7893(2) 0.45469(18) 0.35425(15) 0.0489(4) Uani d . 1 1 . .
C C9 0.7673(2) 0.43606(18) 0.46724(15) 0.0502(4) Uani d . 1 1 . .
H H9 0.7764 0.3590 0.4890 0.060 Uiso calc R 1 1 . .
C C10 0.7285(2) 0.55756(18) 0.54247(15) 0.0480(4) Uani d . 1 1 . .
C C11 0.6912(2) 0.59545(18) 0.67292(15) 0.0490(4) Uani d . 1 1 . .
C C12 0.7055(2) 0.5107(2) 0.74363(17) 0.0599(5) Uani d . 1 1 . .
H H12 0.7390 0.4291 0.7082 0.072 Uiso calc R 1 1 . .
C C13 0.6705(3) 0.5465(2) 0.86630(18) 0.0663(5) Uani d . 1 1 . .
H H13 0.6798 0.4896 0.9133 0.080 Uiso calc R 1 1 . .
C C14 0.6221(2) 0.6670(2) 0.91642(17) 0.0633(5) Uani d . 1 1 . .
C C15 0.6065(3) 0.7534(2) 0.85037(18) 0.0642(5) Uani d . 1 1 . .
H H15 0.5733 0.8349 0.8870 0.077 Uiso calc R 1 1 . .
C C16 0.6412(2) 0.7171(2) 0.72777(17) 0.0564(4) Uani d . 1 1 . .
H H16 0.6309 0.7747 0.6817 0.068 Uiso calc R 1 1 . .
C C17 0.8260(2) 0.35999(19) 0.23761(16) 0.0535(4) Uani d . 1 1 . .
C C18 0.8920(3) 0.1438(2) 0.1458(2) 0.0723(6) Uani d . 1 1 . .
H H18A 0.9889 0.1920 0.1161 0.087 Uiso calc R 1 1 . .
H H18B 0.7970 0.1014 0.0776 0.087 Uiso calc R 1 1 . .
C C19 0.9320(3) 0.0317(3) 0.1868(3) 0.0882(7) Uani d . 1 1 . .
H H19A 1.0243 0.0751 0.2555 0.132 Uiso calc R 1 1 . .
H H19B 0.9631 -0.0351 0.1177 0.132 Uiso calc R 1 1 . .
H H19C 0.8343 -0.0171 0.2136 0.132 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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
C17 O2 C18 . . 115.92(15) ?
N2 N1 C8 . . 111.63(13) ?
N2 N1 C7 . . 118.43(15) ?
C8 N1 C7 . . 129.72(15) ?
C10 N2 N1 . . 105.41(14) ?
C2 C1 C6 . . 121.27(19) ?
C2 C1 Cl1 . . 119.37(15) ?
C6 C1 Cl1 . . 119.37(17) ?
C1 C2 C3 . . 118.90(17) ?
C1 C2 H2 . . 120.6 ?
C3 C2 H2 . . 120.6 ?
C2 C3 C4 . . 121.55(17) ?
C2 C3 H3 . . 119.2 ?
C4 C3 H3 . . 119.2 ?
C5 C4 C3 . . 118.05(18) ?
C5 C4 C7 . . 120.71(16) ?
C3 C4 C7 . . 121.22(16) ?
C6 C5 C4 . . 121.21(18) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C5 C6 C1 . . 119.02(19) ?
C5 C6 H6 . . 120.5 ?
C1 C6 H6 . . 120.5 ?
N1 C7 C4 . . 112.17(14) ?
N1 C7 H7A . . 109.2 ?
C4 C7 H7A . . 109.2 ?
N1 C7 H7B . . 109.2 ?
C4 C7 H7B . . 109.2 ?
H7A C7 H7B . . 107.9 ?
N1 C8 C9 . . 106.76(15) ?
N1 C8 C17 . . 122.96(15) ?
C9 C8 C17 . . 130.22(17) ?
C8 C9 C10 . . 105.43(15) ?
C8 C9 H9 . . 127.3 ?
C10 C9 H9 . . 127.3 ?
N2 C10 C9 . . 110.77(15) ?
N2 C10 C11 . . 119.71(15) ?
C9 C10 C11 . . 129.52(15) ?
C16 C11 C12 . . 118.60(17) ?
C16 C11 C10 . . 120.50(16) ?
C12 C11 C10 . . 120.90(16) ?
C13 C12 C11 . . 120.85(19) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C14 C13 C12 . . 118.54(18) ?
C14 C13 H13 . . 120.7 ?
C12 C13 H13 . . 120.7 ?
F1 C14 C13 . . 118.73(19) ?
F1 C14 C15 . . 118.72(19) ?
C13 C14 C15 . . 122.55(18) ?
C14 C15 C16 . . 118.70(19) ?
C14 C15 H15 . . 120.6 ?
C16 C15 H15 . . 120.6 ?
C15 C16 C11 . . 120.75(18) ?
C15 C16 H16 . . 119.6 ?
C11 C16 H16 . . 119.6 ?
O1 C17 O2 . . 124.03(17) ?
O1 C17 C8 . . 125.40(18) ?
O2 C17 C8 . . 110.57(15) ?
O2 C18 C19 . . 107.60(18) ?
O2 C18 H18A . . 110.2 ?
C19 C18 H18A . . 110.2 ?
O2 C18 H18B . . 110.2 ?
C19 C18 H18B . . 110.2 ?
H18A C18 H18B . . 108.5 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 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 C1 . 1.753(2) ?
F1 C14 . 1.363(2) ?
O1 C17 . 1.210(2) ?
O2 C17 . 1.331(2) ?
O2 C18 . 1.454(2) ?
N1 N2 . 1.348(2) ?
N1 C8 . 1.362(2) ?
N1 C7 . 1.466(2) ?
N2 C10 . 1.343(2) ?
C1 C2 . 1.373(3) ?
C1 C6 . 1.381(3) ?
C2 C3 . 1.379(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.389(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.387(3) ?
C4 C7 . 1.512(3) ?
C5 C6 . 1.380(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.375(2) ?
C8 C17 . 1.470(2) ?
C9 C10 . 1.398(2) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.477(2) ?
C11 C16 . 1.390(3) ?
C11 C12 . 1.392(2) ?
C12 C13 . 1.388(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.366(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.368(3) ?
C15 C16 . 1.387(3) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C18 C19 . 1.488(3) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
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
C8 N1 N2 C10 . . . . -0.88(18) ?
C7 N1 N2 C10 . . . . -175.99(14) ?
C6 C1 C2 C3 . . . . -0.1(3) ?
Cl1 C1 C2 C3 . . . . -179.55(14) ?
C1 C2 C3 C4 . . . . 0.3(3) ?
C2 C3 C4 C5 . . . . -0.5(3) ?
C2 C3 C4 C7 . . . . 177.88(16) ?
C3 C4 C5 C6 . . . . 0.4(3) ?
C7 C4 C5 C6 . . . . -177.99(18) ?
C4 C5 C6 C1 . . . . -0.1(3) ?
C2 C1 C6 C5 . . . . 0.0(3) ?
Cl1 C1 C6 C5 . . . . 179.45(16) ?
N2 N1 C7 C4 . . . . 95.64(18) ?
C8 N1 C7 C4 . . . . -78.4(2) ?
C5 C4 C7 N1 . . . . -57.5(2) ?
C3 C4 C7 N1 . . . . 124.17(18) ?
N2 N1 C8 C9 . . . . 0.85(19) ?
C7 N1 C8 C9 . . . . 175.25(16) ?
N2 N1 C8 C17 . . . . 178.25(15) ?
C7 N1 C8 C17 . . . . -7.3(3) ?
N1 C8 C9 C10 . . . . -0.45(18) ?
C17 C8 C9 C10 . . . . -177.60(17) ?
N1 N2 C10 C9 . . . . 0.57(18) ?
N1 N2 C10 C11 . . . . -179.09(14) ?
C8 C9 C10 N2 . . . . -0.08(19) ?
C8 C9 C10 C11 . . . . 179.54(16) ?
N2 C10 C11 C16 . . . . 5.1(2) ?
C9 C10 C11 C16 . . . . -174.51(17) ?
N2 C10 C11 C12 . . . . -174.77(16) ?
C9 C10 C11 C12 . . . . 5.6(3) ?
C16 C11 C12 C13 . . . . 0.1(3) ?
C10 C11 C12 C13 . . . . 179.94(17) ?
C11 C12 C13 C14 . . . . -0.2(3) ?
C12 C13 C14 F1 . . . . 179.67(17) ?
C12 C13 C14 C15 . . . . 0.2(3) ?
F1 C14 C15 C16 . . . . -179.51(17) ?
C13 C14 C15 C16 . . . . 0.0(3) ?
C14 C15 C16 C11 . . . . -0.1(3) ?
C12 C11 C16 C15 . . . . 0.1(3) ?
C10 C11 C16 C15 . . . . -179.79(16) ?
C18 O2 C17 O1 . . . . 1.5(3) ?
C18 O2 C17 C8 . . . . -178.52(16) ?
N1 C8 C17 O1 . . . . -1.4(3) ?
C9 C8 C17 O1 . . . . 175.33(19) ?
N1 C8 C17 O2 . . . . 178.63(15) ?
C9 C8 C17 O2 . . . . -4.6(3) ?
C17 O2 C18 C19 . . . . 174.11(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21498829
