#------------------------------------------------------------------------------
#$Date: 2025-08-23 01:36:08 +0200 (Sat 23 de Aug de 2025) $
#$Revision: 301880 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/04/8100430.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_8100430
loop_
_publ_author_name
'Casellato, U.'
'Graziani, R.'
'Teijeira, M.'
'Uriarte, E.'
_publ_section_title
;
Crystal structure of {2-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl-
methyl]cyclopentyl}-(4-fluorophenyl)-methanone, C₂₄H₂₇ClFNO₂
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              437
_journal_page_last               438
_journal_volume                  218
_journal_year                    2003
_chemical_formula_structural     'C24 H27 Cl1 F1 N1 O2'
_chemical_formula_sum            'C24 H27 Cl F N O2'
_chemical_formula_weight         416.92
_chemical_melting_point          105.0(10)
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                87.18(3)
_cell_angle_beta                 67.27(3)
_cell_angle_gamma                88.01(3)
_cell_formula_units_Z            2
_cell_length_a                   9.494(2)
_cell_length_b                   10.769(2)
_cell_length_c                   11.377(3)
_cell_measurement_temperature    293
_cell_volume                     1071.4(5)
_diffrn_ambient_temperature      293
_exptl_crystal_density_diffrn    1.292
_refine_ls_R_factor_obs          0.0761
_refine_ls_wR_factor_obs         0.3021
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '104-106' was changed to '105.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_formula_sum        'C24 H27 Cl1 F1 N1 O2'
_cod_database_code               8100430
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Cl1 Cl 0.3516(2) 0.1770(2) 0.48761(13) 0.1062(6) Uani 1 d . .
F1 F 0.1101(3) 0.2682(4) 0.0346(3) 0.1099(11) Uani 1 d . .
O1 O 0.7367(3) 0.4975(3) -0.3185(3) 0.0847(9) Uani 1 d . .
O2 O 0.9284(4) 0.0683(4) -0.0677(3) 0.0878(11) Uani 1 d . .
HO2 H 0.9794(54) 0.1075(44) -0.0310(50) 0.080 Uiso 1 d . .
N1 N 0.8398(4) 0.1902(3) -0.3250(3) 0.0649(8) Uani 1 d . .
C1 C 0.2454(4) 0.3044(5) -0.0578(4) 0.0739(11) Uani 1 d . .
C2 C 0.3109(5) 0.2310(5) -0.1580(5) 0.0832(13) Uani 1 d . .
H2 H 0.2645(5) 0.1581(5) -0.1636(5) 0.080 Uiso 1 calc R .
C3 C 0.4487(5) 0.2663(4) -0.2523(4) 0.0724(11) Uani 1 d . .
H3 H 0.4954(5) 0.2159(4) -0.3214(4) 0.080 Uiso 1 calc R .
C4 C 0.5179(4) 0.3745(3) -0.2456(4) 0.0573(8) Uani 1 d . .
C5 C 0.4468(5) 0.4459(4) -0.1399(4) 0.0778(12) Uani 1 d . .
H5 H 0.4927(5) 0.5183(4) -0.1323(4) 0.080 Uiso 1 calc R .
C6 C 0.3081(5) 0.4112(5) -0.0449(5) 0.0845(13) Uani 1 d . .
H6 H 0.2600(5) 0.4599(5) 0.0254(5) 0.080 Uiso 1 calc R .
C7 C 0.6671(5) 0.4178(4) -0.3446(4) 0.0647(9) Uani 1 d . .
C8 C 0.7273(4) 0.3680(4) -0.4769(4) 0.0686(10) Uani 1 d . .
H8 H 0.6622(4) 0.3004(4) -0.4794(4) 0.080 Uiso 1 calc R .
C9 C 0.7349(7) 0.4677(6) -0.5808(5) 0.105(2) Uani 1 d . .
H91 H 0.6357(7) 0.4797(6) -0.5862(5) 0.080 Uiso 1 calc R .
H92 H 0.7671(7) 0.5464(6) -0.5625(5) 0.080 Uiso 1 calc R .
C10 C 0.8491(7) 0.4196(6) -0.7027(5) 0.098(2) Uani 1 d . .
H101 H 0.9116(7) 0.4869(6) -0.7543(5) 0.080 Uiso 1 calc R .
H102 H 0.7974(7) 0.3830(6) -0.7510(5) 0.080 Uiso 1 calc R .
C11 C 0.9474(5) 0.3228(6) -0.6689(4) 0.0846(13) Uani 1 d . .
H111 H 1.0543(5) 0.3446(6) -0.7088(4) 0.080 Uiso 1 calc R .
H112 H 0.9347(5) 0.2420(6) -0.6971(4) 0.080 Uiso 1 calc R .
C12 C 0.8934(4) 0.3209(4) -0.5229(4) 0.0681(10) Uani 1 d . .
H121 H 0.9534(4) 0.3805(4) -0.5000(4) 0.080 Uiso 1 calc R .
C13 C 0.9101(5) 0.1944(4) -0.4656(4) 0.0727(11) Uani 1 d . .
H131 H 0.8628(5) 0.1329(4) -0.4974(4) 0.080 Uiso 1 calc R .
H132 H 1.0178(5) 0.1727(4) -0.4928(4) 0.080 Uiso 1 calc R .
C14 C 0.9293(4) 0.2541(4) -0.2682(4) 0.0692(10) Uani 1 d . .
H141 H 0.9535(4) 0.3369(4) -0.3073(4) 0.080 Uiso 1 calc R .
H142 H 1.0244(4) 0.2089(4) -0.2831(4) 0.080 Uiso 1 calc R .
C15 C 0.8396(4) 0.2631(4) -0.1267(4) 0.0618(9) Uani 1 d . .
H151 H 0.9011(4) 0.3039(4) -0.0895(4) 0.080 Uiso 1 calc R .
H152 H 0.7489(4) 0.3142(4) -0.1129(4) 0.080 Uiso 1 calc R .
C16 C 0.7924(4) 0.1369(4) -0.0594(4) 0.0624(9) Uani 1 d . .
C17 C 0.7179(5) 0.0626(4) -0.1309(4) 0.0695(10) Uani 1 d . .
H171 H 0.7047(5) -0.0225(4) -0.0970(4) 0.080 Uiso 1 calc R .
H172 H 0.6175(5) 0.0980(4) -0.1167(4) 0.080 Uiso 1 calc R .
C18 C 0.8123(6) 0.0629(4) -0.2728(4) 0.0751(11) Uani 1 d . .
H181 H 0.9090(6) 0.0201(4) -0.2882(4) 0.080 Uiso 1 calc R .
H182 H 0.7587(6) 0.0190(4) -0.3151(4) 0.080 Uiso 1 calc R .
C19 C 0.6852(4) 0.1485(3) 0.0786(4) 0.0562(8) Uani 1 d . .
C20 C 0.7221(5) 0.1047(4) 0.1813(4) 0.0700(10) Uani 1 d . .
H201 H 0.8176(5) 0.0680(4) 0.1651(4) 0.080 Uiso 1 calc R .
C21 C 0.6214(5) 0.1146(4) 0.3045(4) 0.0752(11) Uani 1 d . .
H211 H 0.6489(5) 0.0846(4) 0.3709(4) 0.080 Uiso 1 calc R .
C22 C 0.4804(5) 0.1683(4) 0.3308(4) 0.0679(10) Uani 1 d . .
C23 C 0.4395(5) 0.2146(4) 0.2339(4) 0.0721(10) Uani 1 d . .
H231 H 0.3441(5) 0.2520(4) 0.2517(4) 0.080 Uiso 1 calc R .
C24 C 0.5419(4) 0.2048(4) 0.1096(4) 0.0685(10) Uani 1 d . .
H241 H 0.5142(4) 0.2371(4) 0.0441(4) 0.080 Uiso 1 calc R .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C22 1.735(4) . ?
F1 C1 1.363(5) . ?
O1 C7 1.216(5) . ?
O2 C16 1.438(4) . ?
O2 HO2 0.88(5) . ?
N1 C18 1.458(6) . ?
N1 C13 1.475(5) . ?
N1 C14 1.457(5) . ?
C1 C6 1.353(7) . ?
C1 C2 1.348(6) . ?
C2 C3 1.385(6) . ?
C2 H2 0.93 . ?
C3 C4 1.377(5) . ?
C3 H3 0.93 . ?
C4 C5 1.386(5) . ?
C4 C7 1.501(5) . ?
C5 C6 1.392(6) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.508(6) . ?
C8 C12 1.533(5) . ?
C8 C9 1.539(7) . ?
C8 H8 0.98 . ?
C9 C10 1.496(7) . ?
C9 H91 0.97 . ?
C9 H92 0.97 . ?
C10 C11 1.508(8) . ?
C10 H101 0.97 . ?
C10 H102 0.97 . ?
C11 C12 1.536(6) . ?
C11 H111 0.97 . ?
C11 H112 0.97 . ?
C12 C13 1.512(6) . ?
C12 H121 0.98 . ?
C13 H131 0.97 . ?
C13 H132 0.97 . ?
C14 C15 1.508(6) . ?
C14 H141 0.97 . ?
C14 H142 0.97 . ?
C15 C16 1.520(6) . ?
C15 H151 0.97 . ?
C15 H152 0.97 . ?
C16 C19 1.514(5) . ?
C16 C17 1.533(6) . ?
C17 C18 1.514(6) . ?
C17 H171 0.97 . ?
C17 H172 0.97 . ?
C18 H181 0.97 . ?
C18 H182 0.97 . ?
C19 C24 1.391(5) . ?
C19 C20 1.400(6) . ?
C20 C21 1.365(6) . ?
C20 H201 0.93 . ?
C21 C22 1.368(6) . ?
C21 H211 0.93 . ?
C22 C23 1.370(7) . ?
C23 C24 1.379(6) . ?
C23 H231 0.93 . ?
C24 H241 0.93 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139206108
