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#$Date: 2023-01-21 10:51:25 +0200 (Sat, 21 Jan 2023) $
#$Revision: 280498 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/65/8106525.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106525
loop_
_publ_author_name
'Xu, Wen-Chang'
'You, Jin-Zong'
'Zhang, Yi-Ping'
'Huang, Xu-Wen'
'Li, Tang-Qi'
'Tong, Sheng-Yue'
'Qi, De-Qiang'
_publ_section_title
;
 Crystal structure of methyl
 1-(4-fluorobenzyl)-3-phenyl-1H-pyrazole-5-carboxylate, C18H15FN2O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              327
_journal_page_last               328
_journal_paper_doi               10.1515/ncrs-2016-0268
_journal_volume                  232
_journal_year                    2017
_chemical_formula_sum            'C18 H15 F N2 O2'
_chemical_formula_weight         310.32
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                107.859(2)
_cell_angle_beta                 92.559(2)
_cell_angle_gamma                99.415(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8272(8)
_cell_length_b                   9.6662(10)
_cell_length_c                   10.9834(12)
_cell_measurement_reflns_used    1382
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.13
_cell_measurement_theta_min      2.65
_cell_volume                     776.31(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD 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  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4513
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.081(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0407
_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)+(0.0632P)²+0.0180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1187
_reflns_number_gt                2047
_reflns_number_total             2868
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0268_suppl.cif
_cod_data_source_block           ffpz2
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               8106525
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.32589(18) 0.87363(16) 0.30960(14) 0.0477(4) Uani 1 1 d . . .
C2 C 0.3806(2) 0.74106(19) 0.25569(17) 0.0629(5) Uani 1 1 d . . .
H2 H 0.3954 0.6808 0.3056 0.075 Uiso 1 1 calc R . .
C3 C 0.4134(2) 0.6975(2) 0.12795(19) 0.0723(5) Uani 1 1 d . . .
H3 H 0.4497 0.6080 0.0925 0.087 Uiso 1 1 calc R . .
C4 C 0.3925(2) 0.7857(2) 0.05324(18) 0.0723(5) Uani 1 1 d . . .
H4 H 0.4126 0.7554 -0.0330 0.087 Uiso 1 1 calc R . .
C5 C 0.3418(2) 0.9191(2) 0.10692(17) 0.0692(5) Uani 1 1 d . . .
H5 H 0.3300 0.9803 0.0574 0.083 Uiso 1 1 calc R . .
C6 C 0.3084(2) 0.96235(18) 0.23367(16) 0.0592(4) Uani 1 1 d . . .
H6 H 0.2735 1.0526 0.2689 0.071 Uiso 1 1 calc R . .
C7 C 0.28512(18) 0.91869(16) 0.44392(15) 0.0477(4) Uani 1 1 d . . .
C8 C 0.23917(19) 1.05074(17) 0.51632(15) 0.0520(4) Uani 1 1 d . . .
H8 H 0.2299 1.1321 0.4898 0.062 Uiso 1 1 calc R . .
C9 C 0.21044(18) 1.03644(17) 0.63412(15) 0.0509(4) Uani 1 1 d . . .
C10 C 0.1616(2) 1.14148(19) 0.74919(17) 0.0593(4) Uani 1 1 d . . .
C11 C 0.2165(2) 0.82323(19) 0.72494(17) 0.0630(5) Uani 1 1 d . . .
H11A H 0.2566 0.8928 0.8099 0.076 Uiso 1 1 calc R . .
H11B H 0.2873 0.7471 0.7082 0.076 Uiso 1 1 calc R . .
C12 C 0.0282(2) 0.75261(17) 0.72320(15) 0.0537(4) Uani 1 1 d . . .
C13 C -0.0484(2) 0.77049(19) 0.83652(17) 0.0618(5) Uani 1 1 d . . .
H13 H 0.0168 0.8256 0.9142 0.074 Uiso 1 1 calc R . .
C14 C -0.2202(2) 0.70778(19) 0.83630(18) 0.0655(5) Uani 1 1 d . . .
H14 H -0.2714 0.7195 0.9128 0.079 Uiso 1 1 calc R . .
C15 C -0.3128(2) 0.62827(18) 0.7209(2) 0.0643(5) Uani 1 1 d . . .
C16 C -0.2427(3) 0.60595(19) 0.60668(19) 0.0719(5) Uani 1 1 d . . .
H16 H -0.3089 0.5499 0.5297 0.086 Uiso 1 1 calc R . .
C17 C -0.0705(2) 0.66886(18) 0.60836(17) 0.0641(5) Uani 1 1 d . . .
H17 H -0.0200 0.6549 0.5315 0.077 Uiso 1 1 calc R . .
C18 C 0.0928(3) 1.3805(2) 0.8290(2) 0.1000(8) Uani 1 1 d . . .
H18A H -0.0016 1.3391 0.8676 0.150 Uiso 1 1 calc R . .
H18B H 0.0577 1.4543 0.7967 0.150 Uiso 1 1 calc R . .
H18C H 0.1913 1.4249 0.8922 0.150 Uiso 1 1 calc R . .
F1 F -0.48454(14) 0.56969(12) 0.71949(13) 0.0901(4) Uani 1 1 d . . .
N1 N 0.28546(16) 0.82659(14) 0.51391(13) 0.0549(4) Uani 1 1 d . . .
N2 N 0.24077(16) 0.90048(15) 0.62995(13) 0.0540(4) Uani 1 1 d . . .
O1 O 0.14536(18) 1.12230(15) 0.85152(13) 0.0829(4) Uani 1 1 d . . .
O2 O 0.13973(17) 1.26468(14) 0.72421(13) 0.0774(4) Uani 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C6 118.45(15) . .
C2 C1 C7 120.88(14) . .
C6 C1 C7 120.66(14) . .
C1 C2 C3 120.43(17) . .
C1 C2 H2 119.8 . .
C3 C2 H2 119.8 . .
C4 C3 C2 120.39(18) . .
C4 C3 H3 119.8 . .
C2 C3 H3 119.8 . .
C5 C4 C3 119.49(18) . .
C5 C4 H4 120.3 . .
C3 C4 H4 120.3 . .
C4 C5 C6 120.22(17) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C5 C6 C1 120.99(16) . .
C5 C6 H6 119.5 . .
C1 C6 H6 119.5 . .
N1 C7 C8 110.32(14) . .
N1 C7 C1 120.75(14) . .
C8 C7 C1 128.91(14) . .
C9 C8 C7 106.08(14) . .
C9 C8 H8 127.0 . .
C7 C8 H8 127.0 . .
N2 C9 C8 106.60(14) . .
N2 C9 C10 123.23(15) . .
C8 C9 C10 130.15(16) . .
O1 C10 O2 124.36(16) . .
O1 C10 C9 126.00(18) . .
O2 C10 C9 109.63(15) . .
N2 C11 C12 112.60(13) . .
N2 C11 H11A 109.1 . .
C12 C11 H11A 109.1 . .
N2 C11 H11B 109.1 . .
C12 C11 H11B 109.1 . .
H11A C11 H11B 107.8 . .
C13 C12 C17 118.68(16) . .
C13 C12 C11 120.39(16) . .
C17 C12 C11 120.93(14) . .
C12 C13 C14 121.02(17) . .
C12 C13 H13 119.5 . .
C14 C13 H13 119.5 . .
C15 C14 C13 118.19(17) . .
C15 C14 H14 120.9 . .
C13 C14 H14 120.9 . .
C16 C15 C14 123.00(17) . .
C16 C15 F1 118.42(18) . .
C14 C15 F1 118.57(17) . .
C15 C16 C17 118.18(18) . .
C15 C16 H16 120.9 . .
C17 C16 H16 120.9 . .
C16 C17 C12 120.91(16) . .
C16 C17 H17 119.5 . .
C12 C17 H17 119.5 . .
O2 C18 H18A 109.5 . .
O2 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
O2 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C7 N1 N2 105.46(12) . .
N1 N2 C9 111.53(12) . .
N1 N2 C11 118.26(13) . .
C9 N2 C11 129.93(14) . .
C10 O2 C18 116.43(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.383(2) .
C1 C6 1.384(2) .
C1 C7 1.470(2) .
C2 C3 1.384(2) .
C2 H2 0.9300 .
C3 C4 1.375(3) .
C3 H3 0.9300 .
C4 C5 1.375(3) .
C4 H4 0.9300 .
C5 C6 1.376(2) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 N1 1.3432(19) .
C7 C8 1.394(2) .
C8 C9 1.367(2) .
C8 H8 0.9300 .
C9 N2 1.3608(19) .
C9 C10 1.469(2) .
C10 O1 1.203(2) .
C10 O2 1.336(2) .
C11 N2 1.4600(19) .
C11 C12 1.516(2) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.381(2) .
C12 C17 1.387(2) .
C13 C14 1.382(2) .
C13 H13 0.9300 .
C14 C15 1.364(3) .
C14 H14 0.9300 .
C15 C16 1.362(3) .
C15 F1 1.3678(19) .
C16 C17 1.382(2) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C18 O2 1.447(2) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
N1 N2 1.3490(18) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -1.3(2) . . . .
C7 C1 C2 C3 177.95(15) . . . .
C1 C2 C3 C4 0.2(3) . . . .
C2 C3 C4 C5 1.2(3) . . . .
C3 C4 C5 C6 -1.5(3) . . . .
C4 C5 C6 C1 0.4(3) . . . .
C2 C1 C6 C5 1.0(2) . . . .
C7 C1 C6 C5 -178.24(15) . . . .
C2 C1 C7 N1 -5.8(2) . . . .
C6 C1 C7 N1 173.41(14) . . . .
C2 C1 C7 C8 175.62(15) . . . .
C6 C1 C7 C8 -5.1(2) . . . .
N1 C7 C8 C9 -0.20(16) . . . .
C1 C7 C8 C9 178.48(14) . . . .
C7 C8 C9 N2 0.59(16) . . . .
C7 C8 C9 C10 178.88(15) . . . .
N2 C9 C10 O1 1.2(3) . . . .
C8 C9 C10 O1 -176.84(17) . . . .
N2 C9 C10 O2 -179.71(13) . . . .
C8 C9 C10 O2 2.2(2) . . . .
N2 C11 C12 C13 -132.85(16) . . . .
N2 C11 C12 C17 47.2(2) . . . .
C17 C12 C13 C14 -0.6(2) . . . .
C11 C12 C13 C14 179.47(15) . . . .
C12 C13 C14 C15 -0.4(3) . . . .
C13 C14 C15 C16 1.2(3) . . . .
C13 C14 C15 F1 -178.00(14) . . . .
C14 C15 C16 C17 -1.0(3) . . . .
F1 C15 C16 C17 178.22(14) . . . .
C15 C16 C17 C12 -0.1(3) . . . .
C13 C12 C17 C16 0.8(2) . . . .
C11 C12 C17 C16 -179.24(15) . . . .
C8 C7 N1 N2 -0.28(16) . . . .
C1 C7 N1 N2 -179.08(12) . . . .
C7 N1 N2 C9 0.67(16) . . . .
C7 N1 N2 C11 175.23(13) . . . .
C8 C9 N2 N1 -0.81(17) . . . .
C10 C9 N2 N1 -179.25(13) . . . .
C8 C9 N2 C11 -174.55(15) . . . .
C10 C9 N2 C11 7.0(2) . . . .
C12 C11 N2 N1 -94.10(16) . . . .
C12 C11 N2 C9 79.3(2) . . . .
O1 C10 O2 C18 -0.2(3) . . . .
C9 C10 O2 C18 -179.35(15) . . . .
