#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/06/2230670.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_2230670
loop_
_publ_author_name
'Li, Yu-Feng'
_publ_section_title
;
 N-(4-Chlorophenyl)-4-methylpiperidine-1-carboxamide
;
_journal_coeditor_code           HB5902
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1796
_journal_paper_doi               10.1107/S1600536811024123
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H17 Cl N2 O'
_chemical_formula_moiety         'C13 H17 Cl N2 O'
_chemical_formula_sum            'C13 H17 Cl N2 O'
_chemical_formula_weight         252.74
_chemical_name_systematic
;
N-(4-Chlorophenyl)-4-methylpiperidine-1-carboxamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.36(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.286(3)
_cell_length_b                   9.1468(18)
_cell_length_c                   10.957(2)
_cell_measurement_reflns_used    1999
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      2.98
_cell_volume                     1325.7(5)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12608
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bar
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.368
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0450
_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)+(0.0806P)²+0.0785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1544
_reflns_number_gt                1999
_reflns_number_total             3038
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5902.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230670
_cod_database_fobs_code          2230670
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_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.83830(4) 0.11364(7) 0.42550(6) 0.0690(2) Uani d . 1 1 . .
O O1 0.44390(10) 0.14454(13) 0.73592(13) 0.0484(4) Uani d . 1 1 . .
C C8 0.57283(13) 0.30099(18) 0.59955(16) 0.0379(4) Uani d . 1 1 . .
N N2 0.49079(11) 0.36204(15) 0.65583(15) 0.0432(4) Uani d . 1 1 . .
H H2A 0.4793 0.4543 0.6491 0.052 Uiso calc R 1 1 . .
C C12 0.63981(15) 0.1297(2) 0.46199(18) 0.0452(5) Uani d . 1 1 . .
H H12A 0.6304 0.0526 0.4067 0.054 Uiso calc R 1 1 . .
C C13 0.55876(14) 0.1876(2) 0.51610(17) 0.0436(4) Uani d . 1 1 . .
H H13A 0.4943 0.1500 0.4963 0.052 Uiso calc R 1 1 . .
N N1 0.35363(11) 0.34976(16) 0.77039(16) 0.0447(4) Uani d . 1 1 . .
C C9 0.66864(14) 0.35849(19) 0.62681(18) 0.0421(4) Uani d . 1 1 . .
H H9A 0.6783 0.4356 0.6820 0.051 Uiso calc R 1 1 . .
C C11 0.73497(14) 0.1877(2) 0.49098(17) 0.0436(4) Uani d . 1 1 . .
C C7 0.42888(13) 0.27715(18) 0.72121(16) 0.0385(4) Uani d . 1 1 . .
C C10 0.75036(14) 0.3019(2) 0.57244(17) 0.0447(4) Uani d . 1 1 . .
H H10A 0.8147 0.3406 0.5908 0.054 Uiso calc R 1 1 . .
C C6 0.30658(13) 0.48409(19) 0.71993(19) 0.0473(5) Uani d . 1 1 . .
H H6A 0.3479 0.5258 0.6603 0.057 Uiso calc R 1 1 . .
H H6B 0.3021 0.5549 0.7851 0.057 Uiso calc R 1 1 . .
C C2 0.29344(15) 0.2735(2) 0.85563(19) 0.0485(5) Uani d . 1 1 . .
H H2B 0.2864 0.3352 0.9264 0.058 Uiso calc R 1 1 . .
H H2C 0.3281 0.1847 0.8840 0.058 Uiso calc R 1 1 . .
C C4 0.13554(16) 0.3713(3) 0.7433(2) 0.0639(6) Uani d . 1 1 . .
H H4A 0.1244 0.4363 0.8119 0.077 Uiso calc R 1 1 . .
C C5 0.20188(15) 0.4518(3) 0.6593(2) 0.0567(5) Uani d . 1 1 . .
H H5A 0.2079 0.3931 0.5866 0.068 Uiso calc R 1 1 . .
H H5B 0.1694 0.5431 0.6335 0.068 Uiso calc R 1 1 . .
C C3 0.19038(16) 0.2355(3) 0.7956(2) 0.0587(6) Uani d . 1 1 . .
H H3A 0.1508 0.1902 0.8554 0.070 Uiso calc R 1 1 . .
H H3B 0.1971 0.1657 0.7302 0.070 Uiso calc R 1 1 . .
C C1 0.0326(2) 0.3348(5) 0.6765(4) 0.1222(14) Uani d . 1 1 . .
H H1A 0.0004 0.4231 0.6459 0.183 Uiso calc R 1 1 . .
H H1B -0.0088 0.2881 0.7323 0.183 Uiso calc R 1 1 . .
H H1C 0.0415 0.2701 0.6094 0.183 Uiso calc R 1 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 C8 C13 . . 119.49(16) ?
C9 C8 N2 . . 119.08(16) ?
C13 C8 N2 . . 121.42(16) ?
C7 N2 C8 . . 121.65(14) ?
C7 N2 H2A . . 119.2 ?
C8 N2 H2A . . 119.2 ?
C11 C12 C13 . . 119.19(17) ?
C11 C12 H12A . . 120.4 ?
C13 C12 H12A . . 120.4 ?
C12 C13 C8 . . 120.52(17) ?
C12 C13 H13A . . 119.7 ?
C8 C13 H13A . . 119.7 ?
C7 N1 C2 . . 119.25(15) ?
C7 N1 C6 . . 124.54(16) ?
C2 N1 C6 . . 113.70(15) ?
C8 C9 C10 . . 120.46(17) ?
C8 C9 H9A . . 119.8 ?
C10 C9 H9A . . 119.8 ?
C10 C11 C12 . . 121.20(17) ?
C10 C11 Cl1 . . 119.10(15) ?
C12 C11 Cl1 . . 119.69(14) ?
O1 C7 N1 . . 123.05(16) ?
O1 C7 N2 . . 121.51(16) ?
N1 C7 N2 . . 115.41(15) ?
C11 C10 C9 . . 119.13(17) ?
C11 C10 H10A . . 120.4 ?
C9 C10 H10A . . 120.4 ?
N1 C6 C5 . . 110.16(16) ?
N1 C6 H6A . . 109.6 ?
C5 C6 H6A . . 109.6 ?
N1 C6 H6B . . 109.6 ?
C5 C6 H6B . . 109.6 ?
H6A C6 H6B . . 108.1 ?
N1 C2 C3 . . 111.16(17) ?
N1 C2 H2B . . 109.4 ?
C3 C2 H2B . . 109.4 ?
N1 C2 H2C . . 109.4 ?
C3 C2 H2C . . 109.4 ?
H2B C2 H2C . . 108.0 ?
C5 C4 C3 . . 109.76(18) ?
C5 C4 C1 . . 111.1(2) ?
C3 C4 C1 . . 112.2(2) ?
C5 C4 H4A . . 107.9 ?
C3 C4 H4A . . 107.9 ?
C1 C4 H4A . . 107.9 ?
C6 C5 C4 . . 112.92(18) ?
C6 C5 H5A . . 109.0 ?
C4 C5 H5A . . 109.0 ?
C6 C5 H5B . . 109.0 ?
C4 C5 H5B . . 109.0 ?
H5A C5 H5B . . 107.8 ?
C2 C3 C4 . . 111.12(19) ?
C2 C3 H3A . . 109.4 ?
C4 C3 H3A . . 109.4 ?
C2 C3 H3B . . 109.4 ?
C4 C3 H3B . . 109.4 ?
H3A C3 H3B . . 108.0 ?
C4 C1 H1A . . 109.5 ?
C4 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C4 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C11 . 1.7441(19) ?
O1 C7 . 1.237(2) ?
C8 C9 . 1.384(2) ?
C8 C13 . 1.384(2) ?
C8 N2 . 1.416(2) ?
N2 C7 . 1.379(2) ?
N2 H2A . 0.8600 ?
C12 C11 . 1.381(3) ?
C12 C13 . 1.382(3) ?
C12 H12A . 0.9300 ?
C13 H13A . 0.9300 ?
N1 C7 . 1.353(2) ?
N1 C2 . 1.462(2) ?
N1 C6 . 1.463(2) ?
C9 C10 . 1.386(3) ?
C9 H9A . 0.9300 ?
C11 C10 . 1.377(3) ?
C10 H10A . 0.9300 ?
C6 C5 . 1.514(3) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C2 C3 . 1.503(3) ?
C2 H2B . 0.9700 ?
C2 H2C . 0.9700 ?
C4 C5 . 1.522(3) ?
C4 C3 . 1.524(3) ?
C4 C1 . 1.526(3) ?
C4 H4A . 0.9800 ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
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
N2 H2A O1 2_656 0.86 2.33 2.940(2) 128
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 745989
