#------------------------------------------------------------------------------
#$Date: 2023-01-12 12:28:41 +0200 (Thu, 12 Jan 2023) $
#$Revision: 280304 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106454.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_8106454
loop_
_publ_author_name
'Zhang, Yang'
'Wang, Su'
'Sun, Juan'
_publ_section_title
;
 The crystal structure of
 1-(4-bromophenyl)-2-(4-(4-fluorophenyl)piperazin-1-yl)ethanol,
 C18H20BrFN2O1
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              125
_journal_page_last               126
_journal_paper_doi               10.1515/ncrs-2016-0180
_journal_volume                  232
_journal_year                    2017
_chemical_formula_sum            'C18 H20 Br F N2 O'
_chemical_formula_weight         379.26
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 93.293(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.1884(10)
_cell_length_b                   5.3673(4)
_cell_length_c                   22.3768(15)
_cell_measurement_reflns_used    3048
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      2.3
_cell_volume                     1701.3(2)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0675
_diffrn_reflns_av_sigmaI/netI    0.0621
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14236
_diffrn_reflns_theta_full        25.14
_diffrn_reflns_theta_max         25.14
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    2.432
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      1.481
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0645P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1384
_reflns_number_gt                1876
_reflns_number_total             3048
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0180_suppl.cif
_cod_data_source_block           mo_gfj_8_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               8106454
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C11 C 0.1945(3) 0.9821(8) 0.13607(17) 0.0556(11) Uani 1 1 d . . .
H11A H 0.1888 0.8043 0.1427 0.067 Uiso 1 1 calc R . .
H11B H 0.1314 1.0513 0.1308 0.067 Uiso 1 1 calc R . .
Br1 Br 0.01866(3) 1.03690(12) 0.41556(2) 0.0852(3) Uani 1 1 d . . .
F1 F 0.4435(2) 0.5371(4) -0.05738(11) 0.0734(7) Uani 1 1 d . . .
N1 N 0.3174(2) 0.9063(6) -0.03156(13) 0.0439(8) Uani 1 1 d . . .
N2 N 0.2458(2) 1.0262(6) 0.08203(14) 0.0502(8) Uani 1 1 d . . .
C13 C 0.1888(3) 1.0892(7) 0.24425(17) 0.0455(10) Uani 1 1 d . . .
C16 C 0.0867(3) 1.0597(8) 0.34515(16) 0.0462(10) Uani 1 1 d . . .
C6 C 0.3637(2) 0.9090(7) -0.08562(15) 0.0401(9) Uani 1 1 d . . .
C1 C 0.4271(3) 0.7216(7) -0.09816(16) 0.0469(10) Uani 1 1 d . . .
C10 C 0.3792(3) 0.9191(8) 0.02302(17) 0.0519(10) Uani 1 1 d . . .
H10A H 0.4051 1.0857 0.0276 0.062 Uiso 1 1 calc R . .
H10B H 0.4313 0.8035 0.0201 0.062 Uiso 1 1 calc R . .
C2 C 0.4742(3) 0.7111(8) -0.14965(18) 0.0586(11) Uani 1 1 d . . .
H2 H 0.5180 0.5856 -0.1551 0.070 Uiso 1 1 calc R . .
C15 C 0.0679(3) 1.2481(8) 0.30512(19) 0.0623(12) Uani 1 1 d . . .
H15 H 0.0212 1.3650 0.3117 0.075 Uiso 1 1 calc R . .
C5 C 0.3477(3) 1.0849(7) -0.13056(17) 0.0496(10) Uani 1 1 d . . .
H5 H 0.3054 1.2141 -0.1248 0.060 Uiso 1 1 calc R . .
C17 C 0.1550(3) 0.8892(9) 0.3352(2) 0.0681(13) Uani 1 1 d . . .
H17 H 0.1680 0.7626 0.3628 0.082 Uiso 1 1 calc R . .
C7 C 0.2387(3) 1.0792(8) -0.02664(18) 0.0585(11) Uani 1 1 d . . .
H7A H 0.1969 1.0697 -0.0625 0.070 Uiso 1 1 calc R . .
H7B H 0.2624 1.2482 -0.0229 0.070 Uiso 1 1 calc R . .
C14 C 0.1196(3) 1.2619(8) 0.25467(18) 0.0621(12) Uani 1 1 d . . .
H14 H 0.1074 1.3898 0.2273 0.074 Uiso 1 1 calc R . .
C12 C 0.2454(3) 1.1001(9) 0.18923(18) 0.0588(11) Uani 1 1 d . . .
H12 H 0.304(3) 1.006(7) 0.198(2) 0.071 Uiso 1 1 calc . . .
C4 C 0.3927(3) 1.0728(8) -0.18343(19) 0.0591(11) Uani 1 1 d . . .
H4 H 0.3797 1.1924 -0.2128 0.071 Uiso 1 1 calc R . .
O1 O 0.2708(3) 1.3456(6) 0.17692(13) 0.0796(10) Uani 1 1 d . . .
H1 H 0.2757 1.3621 0.1408 0.119 Uiso 1 1 calc R . .
C18 C 0.2046(3) 0.9034(8) 0.2848(2) 0.0633(12) Uani 1 1 d . . .
H18 H 0.2501 0.7835 0.2781 0.076 Uiso 1 1 calc R . .
C8 C 0.1848(3) 1.0141(9) 0.02744(18) 0.0642(12) Uani 1 1 d . . .
H8A H 0.1325 1.1291 0.0304 0.077 Uiso 1 1 calc R . .
H8B H 0.1590 0.8474 0.0228 0.077 Uiso 1 1 calc R . .
C3 C 0.4561(3) 0.8883(9) -0.19345(18) 0.0603(12) Uani 1 1 d . . .
H3 H 0.4865 0.8823 -0.2291 0.072 Uiso 1 1 calc R . .
C9 C 0.3247(3) 0.8551(8) 0.07650(17) 0.0557(11) Uani 1 1 d . . .
H9A H 0.3011 0.6860 0.0726 0.067 Uiso 1 1 calc R . .
H9B H 0.3663 0.8635 0.1124 0.067 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'
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'
Br Br -0.2901 2.4595 '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
N2 C11 C12 110.3(3) . .
C6 N1 C7 117.0(3) . .
C6 N1 C10 115.4(3) . .
C7 N1 C10 109.4(3) . .
C8 N2 C9 108.8(3) . .
C8 N2 C11 112.6(3) . .
C9 N2 C11 112.8(3) . .
C18 C13 C14 118.2(4) . .
C18 C13 C12 119.9(4) . .
C14 C13 C12 122.0(4) . .
C17 C16 C15 120.3(4) . .
C17 C16 Br1 119.6(3) . .
C15 C16 Br1 120.1(3) . .
C5 C6 C1 115.3(3) . .
C5 C6 N1 124.3(3) . .
C1 C6 N1 120.4(3) . .
F1 C1 C2 117.7(4) . .
F1 C1 C6 118.7(3) . .
C2 C1 C6 123.6(4) . .
N1 C10 C9 110.1(3) . .
C1 C2 C3 119.4(4) . .
C16 C15 C14 118.8(4) . .
C4 C5 C6 121.7(4) . .
C16 C17 C18 120.2(4) . .
N1 C7 C8 109.8(3) . .
C13 C14 C15 121.2(4) . .
O1 C12 C11 111.1(4) . .
O1 C12 C13 110.6(3) . .
C11 C12 C13 112.1(4) . .
C3 C4 C5 121.2(4) . .
C13 C18 C17 121.3(4) . .
N2 C8 C7 111.0(3) . .
C4 C3 C2 118.8(4) . .
N2 C9 C10 110.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C11 N2 1.466(5) .
C11 C12 1.497(6) .
Br1 C16 1.898(4) .
F1 C1 1.357(4) .
N1 C6 1.410(4) .
N1 C7 1.461(5) .
N1 C10 1.464(5) .
N2 C8 1.458(5) .
N2 C9 1.459(5) .
C13 C18 1.358(6) .
C13 C14 1.380(5) .
C13 C12 1.509(5) .
C16 C17 1.361(6) .
C16 C15 1.367(5) .
C6 C5 1.389(5) .
C6 C1 1.389(5) .
C1 C2 1.365(5) .
C10 C9 1.501(5) .
C2 C3 1.379(6) .
C15 C14 1.383(5) .
C5 C4 1.378(5) .
C17 C18 1.366(6) .
C7 C8 1.509(6) .
C12 O1 1.398(5) .
C4 C3 1.365(6) .
