#------------------------------------------------------------------------------
#$Date: 2022-11-16 11:51:26 +0200 (Wed, 16 Nov 2022) $
#$Revision: 279325 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/61/8106121.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_8106121
loop_
_publ_author_name
'Tong, Sheng-Yue'
'You, Jin-Zong'
'Zhang, Yi-Ping'
'Wang, Zhen-Zhen'
'Yu, Ke-Ji'
'Hu, Qiong'
'Pan, Hui-Juan'
'Wu, Cheng-Jie'
'Qi, De-Qiang'
_publ_section_title
;
 Crystal structure of ethyl
 1-(4-fluorobenzyl)-3-phenyl-1H-pyrazole-5-carboxylate, C19H17FN2O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              269
_journal_page_last               270
_journal_paper_doi               10.1515/ncrs-2017-0266
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C19 H17 F N2 O2'
_chemical_formula_weight         324.34
_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     dual
_cell_angle_alpha                108.914(18)
_cell_angle_beta                 92.931(3)
_cell_angle_gamma                99.544(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8593(19)
_cell_length_b                   10.3322(18)
_cell_length_c                   10.9747(19)
_cell_measurement_reflns_used    3216
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.427
_cell_measurement_theta_min      2.644
_cell_volume                     826.1(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXT (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0140
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6650
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_min         3.056
_exptl_absorpt_coefficient_mu    0.093
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3524
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0431
_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)+(0.0519P)²+0.1652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1170
_reflns_number_gt                2739
_reflns_number_total             3524
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2017-0266_suppl.cif
_cod_data_source_block           ffpz2
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               8106121
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.01323(14) -0.58034(13) -0.21251(12) 0.0901(4) Uani 1 1 d . . . . .
O1 O -0.64722(14) -1.23471(11) -0.23397(10) 0.0546(3) Uani 1 1 d . . . . .
O2 O -0.65599(16) -1.09658(12) -0.35449(10) 0.0631(3) Uani 1 1 d . . . . .
N1 N -0.74054(15) -0.89038(12) -0.12490(11) 0.0445(3) Uani 1 1 d . . . . .
N2 N -0.78245(15) -0.82174(12) -0.00687(11) 0.0478(3) Uani 1 1 d . . . . .
C1 C -0.1830(2) -0.63934(18) -0.21325(18) 0.0607(4) Uani 1 1 d . . . . .
C2 C -0.2740(2) -0.72360(17) -0.32873(15) 0.0565(4) Uani 1 1 d . . . . .
H2 H -0.2223 -0.7409 -0.4053 0.068 Uiso 1 1 calc R . . . .
C3 C -0.4450(2) -0.78248(16) -0.32874(14) 0.0511(4) Uani 1 1 d . . . . .
H3 H -0.5088 -0.8409 -0.4064 0.061 Uiso 1 1 calc R . . . .
C4 C -0.52324(19) -0.75619(14) -0.21538(13) 0.0456(3) Uani 1 1 d . . . . .
C5 C -0.7127(2) -0.81596(16) -0.21714(15) 0.0515(4) Uani 1 1 d . . . . .
H5A H -0.7774 -0.7409 -0.1966 0.062 Uiso 1 1 calc R . . . .
H5B H -0.7572 -0.8794 -0.3037 0.062 Uiso 1 1 calc R . . . .
C6 C -0.78467(16) -0.91048(14) 0.05959(13) 0.0418(3) Uani 1 1 d . . . . .
C7 C -0.74270(17) -1.03579(14) -0.01670(13) 0.0434(3) Uani 1 1 d . . . . .
H7 H -0.7356 -1.1136 0.0069 0.052 Uiso 1 1 calc R . . . .
C8 C -0.71420(17) -1.01971(14) -0.13383(13) 0.0418(3) Uani 1 1 d . . . . .
C9 C -0.66953(18) -1.11765(15) -0.25349(13) 0.0450(3) Uani 1 1 d . . . . .
C10 C -0.6040(2) -1.34105(16) -0.34517(15) 0.0589(4) Uani 1 1 d . . . . .
H10A H -0.4985 -1.3049 -0.3751 0.071 Uiso 1 1 calc R . . . .
H10B H -0.6972 -1.3712 -0.4156 0.071 Uiso 1 1 calc R . . . .
C11 C -0.5793(3) -1.45924(19) -0.3017(2) 0.0777(5) Uani 1 1 d . . . . .
H11A H -0.5523 -1.5329 -0.3731 0.117 Uiso 1 1 calc GR . . . .
H11B H -0.6840 -1.4930 -0.2710 0.117 Uiso 1 1 calc GR . . . .
H11C H -0.4857 -1.4283 -0.2330 0.117 Uiso 1 1 calc GR . . . .
C12 C -0.82513(17) -0.86888(15) 0.19470(13) 0.0447(3) Uani 1 1 d . . . . .
C13 C -0.8751(2) -0.74226(17) 0.25307(16) 0.0572(4) Uani 1 1 d . . . . .
H13 H -0.8883 -0.6838 0.2056 0.069 Uiso 1 1 calc R . . . .
C14 C -0.9056(2) -0.7029(2) 0.38276(17) 0.0695(5) Uani 1 1 d . U . . .
H14 H -0.9373 -0.6174 0.4220 0.083 Uiso 1 1 calc R . . . .
C15 C -0.8892(2) -0.7896(2) 0.45337(17) 0.0704(5) Uani 1 1 d . U . . .
H15 H -0.9096 -0.7625 0.5399 0.084 Uiso 1 1 calc R . . . .
C16 C -0.8429(2) -0.9155(2) 0.39602(16) 0.0663(5) Uani 1 1 d . . . . .
H16 H -0.8329 -0.9745 0.4434 0.080 Uiso 1 1 calc R . . . .
C17 C -0.8108(2) -0.95507(17) 0.26763(15) 0.0549(4) Uani 1 1 d . . . . .
H17 H -0.7791 -1.0408 0.2295 0.066 Uiso 1 1 calc R . . . .
C18 C -0.4251(2) -0.67022(18) -0.10037(15) 0.0623(4) Uani 1 1 d . . . . .
H18 H -0.4756 -0.6519 -0.0233 0.075 Uiso 1 1 calc R . . . .
C19 C -0.2534(2) -0.6114(2) -0.09867(18) 0.0722(5) Uani 1 1 d . . . . .
H19 H -0.1876 -0.5542 -0.0214 0.087 Uiso 1 1 calc R . . . .
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'
F F 0.0171 0.0103 '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'
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
C9 O1 C10 115.48(12) . .
N2 N1 C5 118.64(11) . .
N2 N1 C8 111.53(11) . .
C8 N1 C5 129.49(12) . .
C6 N2 N1 105.49(11) . .
C2 C1 F1 118.47(16) . .
C19 C1 F1 118.62(16) . .
C19 C1 C2 122.91(16) . .
C1 C2 H2 120.9 . .
C1 C2 C3 118.14(15) . .
C3 C2 H2 120.9 . .
C2 C3 H3 119.4 . .
C2 C3 C4 121.24(14) . .
C4 C3 H3 119.4 . .
C3 C4 C5 120.88(13) . .
C3 C4 C18 118.46(15) . .
C18 C4 C5 120.63(13) . .
N1 C5 C4 112.47(11) . .
N1 C5 H5A 109.1 . .
N1 C5 H5B 109.1 . .
C4 C5 H5A 109.1 . .
C4 C5 H5B 109.1 . .
H5A C5 H5B 107.8 . .
N2 C6 C7 110.63(12) . .
N2 C6 C12 120.35(12) . .
C7 C6 C12 129.01(13) . .
C6 C7 H7 127.3 . .
C8 C7 C6 105.44(12) . .
C8 C7 H7 127.3 . .
N1 C8 C7 106.90(12) . .
N1 C8 C9 122.63(12) . .
C7 C8 C9 130.44(13) . .
O1 C9 C8 109.85(12) . .
O2 C9 O1 124.50(13) . .
O2 C9 C8 125.64(14) . .
O1 C10 H10A 110.4 . .
O1 C10 H10B 110.4 . .
O1 C10 C11 106.73(14) . .
H10A C10 H10B 108.6 . .
C11 C10 H10A 110.4 . .
C11 C10 H10B 110.4 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C13 C12 C6 121.12(14) . .
C13 C12 C17 118.49(14) . .
C17 C12 C6 120.37(13) . .
C12 C13 H13 120.0 . .
C12 C13 C14 119.91(16) . .
C14 C13 H13 120.0 . .
C13 C14 H14 119.7 . .
C15 C14 C13 120.54(17) . .
C15 C14 H14 119.7 . .
C14 C15 H15 120.0 . .
C16 C15 C14 119.93(16) . .
C16 C15 H15 120.0 . .
C15 C16 H16 120.0 . .
C15 C16 C17 120.00(18) . .
C17 C16 H16 120.0 . .
C12 C17 H17 119.4 . .
C16 C17 C12 121.11(16) . .
C16 C17 H17 119.4 . .
C4 C18 H18 119.5 . .
C19 C18 C4 120.96(15) . .
C19 C18 H18 119.5 . .
C1 C19 C18 118.28(16) . .
C1 C19 H19 120.9 . .
C18 C19 H19 120.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C1 1.3702(19) .
O1 C9 1.3320(18) .
O1 C10 1.4520(17) .
O2 C9 1.2033(17) .
N1 N2 1.3471(16) .
N1 C5 1.4613(18) .
N1 C8 1.3591(17) .
N2 C6 1.3426(18) .
C1 C2 1.364(2) .
C1 C19 1.364(2) .
C2 H2 0.9300 .
C2 C3 1.380(2) .
C3 H3 0.9300 .
C3 C4 1.384(2) .
C4 C5 1.511(2) .
C4 C18 1.387(2) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C7 1.3976(19) .
C6 C12 1.4713(19) .
C7 H7 0.9300 .
C7 C8 1.3732(19) .
C8 C9 1.4749(19) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C10 C11 1.484(2) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 C13 1.389(2) .
C12 C17 1.390(2) .
C13 H13 0.9300 .
C13 C14 1.393(2) .
C14 H14 0.9300 .
C14 C15 1.377(3) .
C15 H15 0.9300 .
C15 C16 1.368(3) .
C16 H16 0.9300 .
C16 C17 1.383(2) .
C17 H17 0.9300 .
C18 H18 0.9300 .
C18 C19 1.382(2) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
F1 C1 C2 C3 -179.90(14) . . . .
F1 C1 C19 C18 179.42(16) . . . .
N1 N2 C6 C7 0.40(15) . . . .
N1 N2 C6 C12 179.58(11) . . . .
N1 C8 C9 O1 178.52(12) . . . .
N1 C8 C9 O2 -1.9(2) . . . .
N2 N1 C5 C4 95.49(15) . . . .
N2 N1 C8 C7 0.81(15) . . . .
N2 N1 C8 C9 178.98(12) . . . .
N2 C6 C7 C8 0.07(15) . . . .
N2 C6 C12 C13 5.2(2) . . . .
N2 C6 C12 C17 -173.64(13) . . . .
C1 C2 C3 C4 0.6(2) . . . .
C2 C1 C19 C18 -0.6(3) . . . .
C2 C3 C4 C5 177.27(13) . . . .
C2 C3 C4 C18 -0.8(2) . . . .
C3 C4 C5 N1 127.98(14) . . . .
C3 C4 C18 C19 0.3(2) . . . .
C4 C18 C19 C1 0.4(3) . . . .
C5 N1 N2 C6 -174.71(12) . . . .
C5 N1 C8 C7 173.93(13) . . . .
C5 N1 C8 C9 -7.9(2) . . . .
C5 C4 C18 C19 -177.78(16) . . . .
C6 C7 C8 N1 -0.52(15) . . . .
C6 C7 C8 C9 -178.49(13) . . . .
C6 C12 C13 C14 -177.30(14) . . . .
C6 C12 C17 C16 177.88(14) . . . .
C7 C6 C12 C13 -175.84(14) . . . .
C7 C6 C12 C17 5.4(2) . . . .
C7 C8 C9 O1 -3.8(2) . . . .
C7 C8 C9 O2 175.77(15) . . . .
C8 N1 N2 C6 -0.75(15) . . . .
C8 N1 C5 C4 -77.21(18) . . . .
C9 O1 C10 C11 178.16(14) . . . .
C10 O1 C9 O2 -0.1(2) . . . .
C10 O1 C9 C8 179.46(12) . . . .
C12 C6 C7 C8 -179.01(13) . . . .
C12 C13 C14 C15 -1.0(3) . . . .
C13 C12 C17 C16 -0.9(2) . . . .
C13 C14 C15 C16 -0.1(3) . . . .
C14 C15 C16 C17 0.7(3) . . . .
C15 C16 C17 C12 -0.1(3) . . . .
C17 C12 C13 C14 1.5(2) . . . .
C18 C4 C5 N1 -53.95(18) . . . .
C19 C1 C2 C3 0.1(3) . . . .
