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#$Date: 2022-11-16 11:48:37 +0200 (Wed, 16 Nov 2022) $
#$Revision: 279324 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/61/8106120.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_8106120
loop_
_publ_author_name
'Wang, Zhen-Zhen'
'You, Jin-Zong'
'Zhang, Yi-Ping'
'Tong, Sheng-Yue'
'Yu, Ke-Ji'
'Hu, Qiong'
'Guo, Yan-Qi'
'Liu, Dan'
'Qi, De-Qiang'
_publ_section_title
;
 Crystal structure of ethyl
 1-(4-bromobenzyl)-3-phenyl-1H-pyrazole-5-carboxylate, C19H17BrN2O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              267
_journal_page_last               268
_journal_paper_doi               10.1515/ncrs-2017-0265
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C19 H17 Br N2 O2'
_chemical_formula_weight         385.25
_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                69.270(2)
_cell_angle_beta                 89.401(2)
_cell_angle_gamma                73.709(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3979(11)
_cell_length_b                   10.4083(14)
_cell_length_c                   11.1696(15)
_cell_measurement_reflns_used    2780
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.112
_cell_measurement_theta_min      2.191
_cell_volume                     872.1(2)
_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 0.925
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0310
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.527
_diffrn_reflns_theta_min         2.820
_exptl_absorpt_coefficient_mu    2.370
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5540
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0523P)²+0.4006P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                2568
_reflns_number_total             3699
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2017-0265_suppl.cif
_cod_data_source_block           qdq2_0m
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               8106120
loop_
_space_group_symop_operation_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
Br1 Br -0.01342(4) 0.97547(4) 0.72591(4) 0.07916(18) Uani 1 1 d . . . . .
O1 O 0.6373(3) 0.2455(2) 0.73657(18) 0.0544(5) Uani 1 1 d . . . . .
O2 O 0.6546(3) 0.3786(2) 0.85307(19) 0.0635(6) Uani 1 1 d . . . . .
N1 N 0.7412(3) 0.5766(2) 0.6222(2) 0.0445(5) Uani 1 1 d . . . . .
N2 N 0.7819(3) 0.6421(2) 0.5042(2) 0.0468(5) Uani 1 1 d . . . . .
C1 C 0.2132(4) 0.8757(3) 0.7221(3) 0.0521(7) Uani 1 1 d . . . . .
C2 C 0.3043(4) 0.7784(3) 0.8345(3) 0.0528(7) Uani 1 1 d . . . . .
H2 H 0.2567 0.7619 0.9120 0.063 Uiso 1 1 calc R . . . .
C3 C 0.4678(4) 0.7055(3) 0.8309(3) 0.0509(7) Uani 1 1 d . . . . .
H3 H 0.5300 0.6388 0.9069 0.061 Uiso 1 1 calc R . . . .
C4 C 0.5420(4) 0.7292(3) 0.7162(2) 0.0463(6) Uani 1 1 d . . . . .
C5 C 0.7218(4) 0.6511(3) 0.7135(3) 0.0526(7) Uani 1 1 d . . . . .
H5A H 0.7855 0.7196 0.6897 0.063 Uiso 1 1 calc R . . . .
H5B H 0.7665 0.5816 0.7989 0.063 Uiso 1 1 calc R . . . .
C6 C 0.7797(3) 0.5553(3) 0.4399(2) 0.0419(6) Uani 1 1 d . . . . .
C7 C 0.7358(3) 0.4347(3) 0.5180(2) 0.0441(6) Uani 1 1 d . . . . .
H7 H 0.7255 0.3590 0.4961 0.053 Uiso 1 1 calc R . . . .
C8 C 0.7112(3) 0.4515(3) 0.6336(2) 0.0416(6) Uani 1 1 d . . . . .
C9 C 0.6656(3) 0.3573(3) 0.7534(3) 0.0452(6) Uani 1 1 d . . . . .
C10 C 0.5869(4) 0.1458(3) 0.8476(3) 0.0608(8) Uani 1 1 d . . . . .
H10A H 0.4921 0.1970 0.8799 0.073 Uiso 1 1 calc R . . . .
H10B H 0.6778 0.0971 0.9158 0.073 Uiso 1 1 calc R . . . .
C11 C 0.5417(5) 0.0400(4) 0.8039(4) 0.0755(10) Uani 1 1 d . . . . .
H11A H 0.4510 0.0894 0.7371 0.113 Uiso 1 1 calc GR . . . .
H11B H 0.5088 -0.0286 0.8750 0.113 Uiso 1 1 calc GR . . . .
H11C H 0.6362 -0.0091 0.7713 0.113 Uiso 1 1 calc GR . . . .
C12 C 0.8188(3) 0.5936(3) 0.3050(3) 0.0441(6) Uani 1 1 d . . . . .
C13 C 0.8754(4) 0.7129(3) 0.2461(3) 0.0545(7) Uani 1 1 d . . . . .
H13 H 0.8923 0.7671 0.2929 0.065 Uiso 1 1 calc R . . . .
C14 C 0.9061(4) 0.7508(4) 0.1183(3) 0.0648(9) Uani 1 1 d . . . . .
H14 H 0.9430 0.8308 0.0793 0.078 Uiso 1 1 calc R . . . .
C15 C 0.8827(4) 0.6709(4) 0.0480(3) 0.0659(9) Uani 1 1 d . . . . .
H15 H 0.9032 0.6972 -0.0380 0.079 Uiso 1 1 calc R . . . .
C16 C 0.8292(4) 0.5530(4) 0.1055(3) 0.0624(8) Uani 1 1 d . . . . .
H16 H 0.8143 0.4984 0.0586 0.075 Uiso 1 1 calc R . . . .
C17 C 0.7972(4) 0.5143(3) 0.2329(3) 0.0534(7) Uani 1 1 d . . . . .
H17 H 0.7606 0.4339 0.2709 0.064 Uiso 1 1 calc R . . . .
C18 C 0.4460(4) 0.8284(3) 0.6043(3) 0.0596(8) Uani 1 1 d . . . . .
H18 H 0.4931 0.8457 0.5265 0.072 Uiso 1 1 calc R . . . .
C19 C 0.2820(4) 0.9019(4) 0.6060(3) 0.0633(8) Uani 1 1 d . . . . .
H19 H 0.2186 0.9681 0.5303 0.076 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 0.0030 0.0020 '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'
Br Br -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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 115.8(2) . .
N2 N1 C5 118.4(2) . .
N2 N1 C8 111.7(2) . .
C8 N1 C5 129.7(2) . .
C6 N2 N1 105.4(2) . .
C2 C1 Br1 119.1(2) . .
C2 C1 C19 121.4(3) . .
C19 C1 Br1 119.5(2) . .
C1 C2 H2 120.6 . .
C1 C2 C3 118.8(3) . .
C3 C2 H2 120.6 . .
C2 C3 H3 119.2 . .
C2 C3 C4 121.6(3) . .
C4 C3 H3 119.2 . .
C3 C4 C5 121.3(3) . .
C18 C4 C3 117.9(3) . .
C18 C4 C5 120.8(3) . .
N1 C5 C4 112.0(2) . .
N1 C5 H5A 109.2 . .
N1 C5 H5B 109.2 . .
C4 C5 H5A 109.2 . .
C4 C5 H5B 109.2 . .
H5A C5 H5B 107.9 . .
N2 C6 C7 110.5(2) . .
N2 C6 C12 120.7(2) . .
C7 C6 C12 128.8(2) . .
C6 C7 H7 127.2 . .
C8 C7 C6 105.5(2) . .
C8 C7 H7 127.2 . .
N1 C8 C7 106.8(2) . .
N1 C8 C9 123.0(2) . .
C7 C8 C9 130.2(2) . .
O1 C9 C8 110.5(2) . .
O2 C9 O1 124.5(3) . .
O2 C9 C8 125.1(3) . .
O1 C10 H10A 110.3 . .
O1 C10 H10B 110.3 . .
O1 C10 C11 107.0(3) . .
H10A C10 H10B 108.6 . .
C11 C10 H10A 110.3 . .
C11 C10 H10B 110.3 . .
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 120.5(3) . .
C17 C12 C6 121.1(2) . .
C17 C12 C13 118.4(3) . .
C12 C13 H13 120.0 . .
C14 C13 C12 120.0(3) . .
C14 C13 H13 120.0 . .
C13 C14 H14 119.7 . .
C15 C14 C13 120.6(3) . .
C15 C14 H14 119.7 . .
C14 C15 H15 120.2 . .
C16 C15 C14 119.7(3) . .
C16 C15 H15 120.2 . .
C15 C16 H16 119.8 . .
C15 C16 C17 120.3(3) . .
C17 C16 H16 119.8 . .
C12 C17 H17 119.5 . .
C16 C17 C12 121.0(3) . .
C16 C17 H17 119.5 . .
C4 C18 H18 119.4 . .
C19 C18 C4 121.2(3) . .
C19 C18 H18 119.4 . .
C1 C19 H19 120.5 . .
C18 C19 C1 119.0(3) . .
C18 C19 H19 120.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.904(3) .
O1 C9 1.326(3) .
O1 C10 1.455(3) .
O2 C9 1.208(3) .
N1 N2 1.343(3) .
N1 C5 1.468(4) .
N1 C8 1.357(3) .
N2 C6 1.341(4) .
C1 C2 1.368(4) .
C1 C19 1.382(4) .
C2 H2 0.9300 .
C2 C3 1.378(4) .
C3 H3 0.9300 .
C3 C4 1.391(4) .
C4 C5 1.506(4) .
C4 C18 1.386(4) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C7 1.397(4) .
C6 C12 1.475(4) .
C7 H7 0.9300 .
C7 C8 1.369(4) .
C8 C9 1.473(4) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C10 C11 1.488(5) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 C13 1.395(4) .
C12 C17 1.385(4) .
C13 H13 0.9300 .
C13 C14 1.383(4) .
C14 H14 0.9300 .
C14 C15 1.380(5) .
C15 H15 0.9300 .
C15 C16 1.366(5) .
C16 H16 0.9300 .
C16 C17 1.381(4) .
C17 H17 0.9300 .
C18 H18 0.9300 .
C18 C19 1.379(5) .
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
Br1 C1 C2 C3 179.3(2) . . . .
Br1 C1 C19 C18 -179.6(3) . . . .
N1 N2 C6 C7 0.5(3) . . . .
N1 N2 C6 C12 179.9(2) . . . .
N1 C8 C9 O1 177.6(2) . . . .
N1 C8 C9 O2 -2.1(4) . . . .
N2 N1 C5 C4 97.1(3) . . . .
N2 N1 C8 C7 0.8(3) . . . .
N2 N1 C8 C9 179.4(2) . . . .
N2 C6 C7 C8 -0.1(3) . . . .
N2 C6 C12 C13 6.7(4) . . . .
N2 C6 C12 C17 -172.0(2) . . . .
C1 C2 C3 C4 0.4(4) . . . .
C2 C1 C19 C18 -0.1(5) . . . .
C2 C3 C4 C5 178.8(3) . . . .
C2 C3 C4 C18 -0.4(4) . . . .
C3 C4 C5 N1 125.9(3) . . . .
C3 C4 C18 C19 0.2(5) . . . .
C4 C18 C19 C1 0.1(5) . . . .
C5 N1 N2 C6 -175.9(2) . . . .
C5 N1 C8 C7 175.2(3) . . . .
C5 N1 C8 C9 -6.2(4) . . . .
C5 C4 C18 C19 -179.1(3) . . . .
C6 C7 C8 N1 -0.4(3) . . . .
C6 C7 C8 C9 -178.9(2) . . . .
C6 C12 C13 C14 -177.8(3) . . . .
C6 C12 C17 C16 178.1(3) . . . .
C7 C6 C12 C13 -174.1(3) . . . .
C7 C6 C12 C17 7.3(4) . . . .
C7 C8 C9 O1 -4.1(4) . . . .
C7 C8 C9 O2 176.2(3) . . . .
C8 N1 N2 C6 -0.8(3) . . . .
C8 N1 C5 C4 -77.0(4) . . . .
C9 O1 C10 C11 173.2(3) . . . .
C10 O1 C9 O2 1.2(4) . . . .
C10 O1 C9 C8 -178.5(2) . . . .
C12 C6 C7 C8 -179.4(2) . . . .
C12 C13 C14 C15 -0.5(5) . . . .
C13 C12 C17 C16 -0.6(4) . . . .
C13 C14 C15 C16 -0.3(5) . . . .
C14 C15 C16 C17 0.6(5) . . . .
C15 C16 C17 C12 -0.1(5) . . . .
C17 C12 C13 C14 0.9(4) . . . .
C18 C4 C5 N1 -54.9(4) . . . .
C19 C1 C2 C3 -0.1(4) . . . .
