#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/66/1546658.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1546658
loop_
_publ_author_name
'Mohamooda Sumaya, U.'
'Reuben Jonathan, D.'
'Era, Dravida Thendral'
'Gomathi, S.'
'Usha, G.'
_publ_section_title
;
 (2,4-Dichlorophenyl)(3-hydroxypiperidin-1-yl)methanone: crystal structure
 and Hirshfeld analysis
;
_journal_coeditor_code           SU4151
_journal_issue                   6
_journal_name_full               IUCrData
_journal_page_first              x170813
_journal_paper_doi               10.1107/S2414314617008136
_journal_volume                  2
_journal_year                    2017
_chemical_formula_iupac          'C12 H13 Cl2 N O2'
_chemical_formula_moiety         'C12 H13 Cl2 N O2'
_chemical_formula_sum            'C12 H13 Cl2 N O2'
_chemical_formula_weight         274.13
_chemical_name_systematic
;
(2,4-Dichlorophenyl)(3-hydroxypiperidin-1-yl)methanone
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9866(6)
_cell_length_b                   7.9972(4)
_cell_length_c                   23.1220(10)
_cell_measurement_reflns_used    7296
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.74
_cell_measurement_theta_min      2.28
_cell_volume                     2586.3(2)
_computing_cell_refinement
;
APEX2 and SAINT (Bruker, 2004)
;
_computing_data_collection
;
APEX2 (Bruker, 2004)
;
_computing_data_reduction
;
SAINT and XPREP (Bruker, 2004)
;
_computing_molecular_graphics
;
ORTEP-3 for windows (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            34472
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.848
_diffrn_reflns_theta_min         2.286
_exptl_absorpt_coefficient_mu    0.491
_exptl_absorpt_correction_T_max  0.9454
_exptl_absorpt_correction_T_min  0.8915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.368
_refine_ls_extinction_coef       0.0031(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2763
_refine_ls_number_restraints     99
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0683P)²+1.3359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1638
_reflns_number_gt                1602
_reflns_number_total             2763
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su4151sup1.cif
_cod_data_source_block           I
_cod_database_code               1546658
_cod_database_fobs_code          1546658
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.847
_shelx_estimated_absorpt_t_max   0.908
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.5092(5) 0.0739(7) 0.6677(3) 0.0590(18) Uani d 0.455(7) A 1
C C1 0.4668(5) -0.0842(8) 0.6489(3) 0.060(2) Uani d 0.455(7) A 1
H H1A 0.4179 -0.0624 0.6201 0.071 Uiso calc 0.455(7) A 1
H H1B 0.4367 -0.1387 0.6817 0.071 Uiso calc 0.455(7) A 1
C C2 0.5422(6) -0.1979(9) 0.6237(4) 0.0564(19) Uani d 0.455(7) A 1
H H2 0.5683 -0.1471 0.5885 0.068 Uiso calc 0.455(7) A 1
C C3 0.6208(9) -0.2243(19) 0.6662(6) 0.067(3) Uani d 0.455(7) A 1
H H3A 0.6706 -0.2914 0.6485 0.081 Uiso calc 0.455(7) A 1
H H3B 0.5963 -0.2856 0.6992 0.081 Uiso calc 0.455(7) A 1
C C4 0.6630(7) -0.0618(12) 0.6866(5) 0.073(2) Uani d 0.455(7) A 1
H H4A 0.6956 -0.0077 0.6546 0.087 Uiso calc 0.455(7) A 1
H H4B 0.7098 -0.0838 0.7166 0.087 Uiso calc 0.455(7) A 1
C C5 0.5869(6) 0.0530(11) 0.7098(4) 0.066(2) Uani d 0.455(7) A 1
H H5A 0.5614 0.0071 0.7454 0.079 Uiso calc 0.455(7) A 1
H H5B 0.6149 0.1611 0.7185 0.079 Uiso calc 0.455(7) A 1
N N1' 0.5416(4) 0.0869(6) 0.6416(3) 0.0533(13) Uani d 0.545(7) A 2
C C1' 0.5157(4) -0.0624(6) 0.6095(2) 0.0505(15) Uani d 0.545(7) A 2
H H1'1 0.5635 -0.0836 0.5800 0.061 Uiso calc 0.545(7) A 2
H H1'2 0.4548 -0.0445 0.5903 0.061 Uiso calc 0.545(7) A 2
C C2' 0.5083(5) -0.2121(7) 0.6488(3) 0.0543(16) Uani d 0.545(7) A 2
H H2' 0.4530 -0.1992 0.6744 0.065 Uiso calc 0.545(7) A 2
C C3' 0.5973(8) -0.2377(16) 0.6844(5) 0.072(3) Uani d 0.545(7) A 2
H H3'1 0.6500 -0.2688 0.6593 0.086 Uiso calc 0.545(7) A 2
H H3'2 0.5871 -0.3277 0.7118 0.086 Uiso calc 0.545(7) A 2
C C4' 0.6221(8) -0.0775(10) 0.7167(4) 0.087(2) Uani d 0.545(7) A 2
H H4'1 0.5736 -0.0565 0.7459 0.104 Uiso calc 0.545(7) A 2
H H4'2 0.6827 -0.0922 0.7365 0.104 Uiso calc 0.545(7) A 2
C C5' 0.6287(5) 0.0717(8) 0.6773(4) 0.0698(19) Uani d 0.545(7) A 2
H H5'1 0.6370 0.1723 0.7002 0.084 Uiso calc 0.545(7) A 2
H H5'2 0.6840 0.0600 0.6523 0.084 Uiso calc 0.545(7) A 2
Cl Cl2 0.28658(9) 0.11880(14) 0.68040(4) 0.0990(4) Uani d 1 . .
Cl Cl1 0.17370(7) 0.32088(17) 0.47207(5) 0.1185(5) Uani d 1 . .
O O2 0.49103(16) -0.3471(2) 0.60880(9) 0.0738(7) Uani d 1 . .
H H2A 0.5240 -0.4291 0.6164 0.111 Uiso calc 1 A 1
O O1 0.52333(18) 0.3567(3) 0.66457(10) 0.0819(7) Uani d 1 . .
C C11 0.2423(2) 0.2233(4) 0.57471(12) 0.0592(7) Uani d 1 . .
H H11 0.1798 0.1935 0.5839 0.071 Uiso calc 1 . .
C C12 0.3156(2) 0.2009(3) 0.61377(12) 0.0557(7) Uani d 1 . .
C C8 0.4269(2) 0.3131(4) 0.54690(12) 0.0578(7) Uani d 1 . .
H H8 0.4889 0.3446 0.5375 0.069 Uiso calc 1 . .
C C7 0.40901(18) 0.2434(3) 0.60078(12) 0.0516(7) Uani d 1 . .
C C10 0.2645(2) 0.2910(4) 0.52185(12) 0.0618(8) Uani d 1 . .
C C6 0.4908(2) 0.2295(4) 0.64243(13) 0.0647(8) Uani d 1 . .
C C9 0.3554(2) 0.3364(4) 0.50740(13) 0.0617(8) Uani d 1 . .
H H9 0.3686 0.3824 0.4713 0.074 Uiso calc 1 . .
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'
Cl Cl 0.1484 0.1585 '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
C6 N1 C1 124.8(5)
C6 N1 C5 121.0(5)
C1 N1 C5 113.4(6)
N1 C1 C2 110.6(6)
N1 C1 H1A 109.5
C2 C1 H1A 109.5
N1 C1 H1B 109.5
C2 C1 H1B 109.5
H1A C1 H1B 108.1
O2 C2 C3 114.1(8)
O2 C2 C1 104.2(6)
C3 C2 C1 110.2(8)
O2 C2 H2 109.4
C3 C2 H2 109.4
C1 C2 H2 109.4
C2 C3 C4 111.9(10)
C2 C3 H3A 109.2
C4 C3 H3A 109.2
C2 C3 H3B 109.2
C4 C3 H3B 109.2
H3A C3 H3B 107.9
C3 C4 C5 111.2(9)
C3 C4 H4A 109.4
C5 C4 H4A 109.4
C3 C4 H4B 109.4
C5 C4 H4B 109.4
H4A C4 H4B 108.0
N1 C5 C4 110.8(7)
N1 C5 H5A 109.5
C4 C5 H5A 109.5
N1 C5 H5B 109.5
C4 C5 H5B 109.5
H5A C5 H5B 108.1
C6 N1' C1' 125.0(4)
C6 N1' C5' 119.9(5)
C1' N1' C5' 115.1(5)
N1' C1' C2' 111.3(4)
N1' C1' H1'1 109.4
C2' C1' H1'1 109.4
N1' C1' H1'2 109.4
C2' C1' H1'2 109.4
H1'1 C1' H1'2 108.0
O2 C2' C1' 102.8(4)
O2 C2' C3' 112.8(7)
C1' C2' C3' 112.4(6)
O2 C2' H2' 109.6
C1' C2' H2' 109.6
C3' C2' H2' 109.6
C2' C3' C4' 110.0(9)
C2' C3' H3'1 109.7
C4' C3' H3'1 109.7
C2' C3' H3'2 109.7
C4' C3' H3'2 109.7
H3'1 C3' H3'2 108.2
C5' C4' C3' 112.5(7)
C5' C4' H4'1 109.1
C3' C4' H4'1 109.1
C5' C4' H4'2 109.1
C3' C4' H4'2 109.1
H4'1 C4' H4'2 107.8
N1' C5' C4' 110.7(6)
N1' C5' H5'1 109.5
C4' C5' H5'1 109.5
N1' C5' H5'2 109.5
C4' C5' H5'2 109.5
H5'1 C5' H5'2 108.1
C2 O2 H2A 109.5
C10 C11 C12 117.8(3)
C10 C11 H11 121.1
C12 C11 H11 121.1
C11 C12 C7 121.9(3)
C11 C12 Cl2 117.4(2)
C7 C12 Cl2 120.7(2)
C9 C8 C7 121.6(3)
C9 C8 H8 119.2
C7 C8 H8 119.2
C12 C7 C8 117.6(2)
C12 C7 C6 124.3(3)
C8 C7 C6 118.0(3)
C9 C10 C11 122.3(3)
C9 C10 Cl1 119.0(2)
C11 C10 Cl1 118.7(2)
O1 C6 N1' 120.9(3)
O1 C6 N1 119.7(3)
O1 C6 C7 119.3(3)
N1' C6 C7 117.2(3)
N1 C6 C7 118.3(3)
C10 C9 C8 118.8(3)
C10 C9 H9 120.6
C8 C9 H9 120.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C6 1.398(7)
N1 C1 1.462(8)
N1 C5 1.469(8)
C1 C2 1.510(10)
C1 H1A 0.9700
C1 H1B 0.9700
C2 O2 1.434(8)
C2 C3 1.491(13)
C2 H2 0.9800
C3 C4 1.503(15)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.504(14)
C4 H4A 0.9700
C4 H4B 0.9700
C5 H5A 0.9700
C5 H5B 0.9700
N1' C6 1.344(6)
N1' C1' 1.452(6)
N1' C5' 1.476(6)
C1' C2' 1.506(7)
C1' H1'1 0.9700
C1' H1'2 0.9700
C2' O2 1.442(7)
C2' C3' 1.507(11)
C2' H2' 0.9800
C3' C4' 1.524(13)
C3' H3'1 0.9700
C3' H3'2 0.9700
C4' C5' 1.505(12)
C4' H4'1 0.9700
C4' H4'2 0.9700
C5' H5'1 0.9700
C5' H5'2 0.9700
Cl2 C12 1.723(3)
Cl1 C10 1.731(3)
O2 H2A 0.8200
O1 C6 1.226(3)
C11 C10 1.372(4)
C11 C12 1.378(4)
C11 H11 0.9300
C12 C7 1.383(4)
C8 C9 1.367(4)
C8 C7 1.387(4)
C8 H8 0.9300
C7 C6 1.500(4)
C10 C9 1.364(4)
C9 H9 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H2A O1 1_545 0.82 2.04 2.735(3) 142
C11 H11 O2 7_665 0.93 2.48 3.404(4) 173
C4' H4'1 O1 4_646 0.97 2.57 3.456(12) 152
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
C6 N1 C1 C2 113.1(9)
C5 N1 C1 C2 -56.9(9)
N1 C1 C2 O2 178.6(5)
N1 C1 C2 C3 55.8(10)
O2 C2 C3 C4 -172.0(8)
C1 C2 C3 C4 -55.2(11)
C2 C3 C4 C5 54.0(13)
C6 N1 C5 C4 -115.2(10)
C1 N1 C5 C4 55.3(10)
C3 C4 C5 N1 -52.7(12)
C6 N1' C1' C2' -123.6(7)
C5' N1' C1' C2' 53.8(7)
N1' C1' C2' O2 -175.0(4)
N1' C1' C2' C3' -53.6(9)
O2 C2' C3' C4' 168.9(6)
C1' C2' C3' C4' 53.4(10)
C2' C3' C4' C5' -53.3(12)
C6 N1' C5' C4' 124.2(9)
C1' N1' C5' C4' -53.3(9)
C3' C4' C5' N1' 52.4(12)
C10 C11 C12 C7 -0.5(4)
C10 C11 C12 Cl2 179.0(2)
C11 C12 C7 C8 1.2(4)
Cl2 C12 C7 C8 -178.3(2)
C11 C12 C7 C6 177.0(3)
Cl2 C12 C7 C6 -2.5(4)
C9 C8 C7 C12 -1.2(4)
C9 C8 C7 C6 -177.3(3)
C12 C11 C10 C9 -0.3(5)
C12 C11 C10 Cl1 -179.8(2)
C1' N1' C6 O1 -170.7(4)
C5' N1' C6 O1 12.1(7)
C1' N1' C6 C7 -8.9(7)
C5' N1' C6 C7 173.9(5)
C1 N1 C6 O1 173.5(6)
C5 N1 C6 O1 -17.2(9)
C1 N1 C6 C7 12.0(9)
C5 N1 C6 C7 -178.6(5)
C12 C7 C6 O1 -105.1(4)
C8 C7 C6 O1 70.7(4)
C12 C7 C6 N1' 92.8(5)
C8 C7 C6 N1' -91.4(4)
C12 C7 C6 N1 56.4(6)
C8 C7 C6 N1 -127.8(5)
C11 C10 C9 C8 0.2(5)
Cl1 C10 C9 C8 179.8(2)
C7 C8 C9 C10 0.5(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139050497
