#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/26/2202633.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_2202633
loop_
_publ_author_name
'Xiao-Jun Zhao'
'Miao Du'
_publ_section_title
;
 2-tert-Butyl-4-methyl-6-(1-piperidiniomethyl)phenol perchlorate
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1161
_journal_page_last               o1162
_journal_paper_doi               10.1107/S1600536803015551
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C17 H28 N O 1+, Cl O4 1-'
_chemical_formula_moiety         'C17 H28 N O 1+, Cl O4 1-'
_chemical_formula_sum            'C17 H28 Cl N O5'
_chemical_formula_weight         361.85
_chemical_name_systematic
; 2-tert-Butyl-4-methyl-6-(piperidyl-N-methyl)phenol
perchlorate
;
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 107.297(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.639(5)
_cell_length_b                   10.390(4)
_cell_length_c                   16.466(6)
_cell_measurement_reflns_used    5481
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.35
_cell_volume                     1901.2(13)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'XP (Bruker, 1998)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'Bruker SMART 1000'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5523
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.9778
_exptl_absorpt_correction_T_min  0.9562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SAINT (Bruker 1998) and SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2656
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0500
_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)+(0.06P)²] where P = (Fₒ²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1300
_reflns_number_gt                1555
_reflns_number_total             3256
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl6045.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1901.1(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2202633
_cod_database_fobs_code          2202633
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_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.7726(2) 0.9106(2) 0.23789(14) 0.0570(7) Uani d D 1 . . O
H1 0.8231 0.8640 0.2272 0.086 Uiso calc RD 1 . . H
N1 1.0332(2) 0.7523(2) 0.40337(16) 0.0398(7) Uani d . 1 . . N
H2 1.0293 0.7381 0.4570 0.048 Uiso calc R 1 . . H
C1 1.1383(3) 0.6783(4) 0.3938(2) 0.0563(10) Uani d . 1 . . C
H1A 1.1430 0.6888 0.3364 0.068 Uiso calc R 1 . . H
H1B 1.1269 0.5875 0.4028 0.068 Uiso calc R 1 . . H
C2 1.2550(3) 0.7229(4) 0.4564(3) 0.0729(13) Uani d . 1 . . C
H2A 1.3217 0.6758 0.4468 0.087 Uiso calc R 1 . . H
H2B 1.2535 0.7051 0.5139 0.087 Uiso calc R 1 . . H
C3 1.2731(3) 0.8660(5) 0.4466(3) 0.0763(13) Uani d . 1 . . C
H3A 1.3460 0.8940 0.4891 0.092 Uiso calc R 1 . . H
H3B 1.2819 0.8831 0.3909 0.092 Uiso calc R 1 . . H
C4 1.1664(3) 0.9399(4) 0.4572(3) 0.0739(13) Uani d . 1 . . C
H4A 1.1622 0.9285 0.5147 0.089 Uiso calc R 1 . . H
H4B 1.1772 1.0310 0.4486 0.089 Uiso calc R 1 . . H
C5 1.0502(3) 0.8948(3) 0.3946(2) 0.0532(10) Uani d . 1 . . C
H5A 0.9832 0.9408 0.4046 0.064 Uiso calc R 1 . . H
H5B 1.0513 0.9137 0.3372 0.064 Uiso calc R 1 . . H
C6 0.9174(3) 0.7042(3) 0.3425(2) 0.0420(9) Uani d . 1 . . C
H6A 0.9133 0.6115 0.3483 0.050 Uiso calc R 1 . . H
H6B 0.9176 0.7224 0.2848 0.050 Uiso calc R 1 . . H
C7 0.8076(3) 0.7640(3) 0.3571(2) 0.0380(8) Uani d . 1 . . C
C8 0.7403(3) 0.8604(3) 0.3054(2) 0.0377(8) Uani d . 1 . . C
C9 0.6360(3) 0.9113(3) 0.3199(2) 0.0375(8) Uani d . 1 . . C
C14 0.5591(3) 1.0149(3) 0.2621(2) 0.0452(9) Uani d . 1 . . C
C16 0.6341(3) 1.1380(3) 0.2647(3) 0.0694(12) Uani d . 1 . . C
H16A 0.6633 1.1686 0.3222 0.104 Uiso calc R 1 . . H
H16B 0.5848 1.2029 0.2297 0.104 Uiso calc R 1 . . H
H16C 0.7010 1.1190 0.2439 0.104 Uiso calc R 1 . . H
C15 0.5108(3) 0.9650(4) 0.1704(2) 0.0677(12) Uani d . 1 . . C
H15A 0.4636 0.8889 0.1695 0.102 Uiso calc R 1 . . H
H15B 0.5770 0.9449 0.1491 0.102 Uiso calc R 1 . . H
H15C 0.4615 1.0300 0.1353 0.102 Uiso calc R 1 . . H
C17 0.4494(3) 1.0524(4) 0.2893(3) 0.0722(12) Uani d . 1 . . C
H17B 0.4004 0.9777 0.2883 0.108 Uiso calc R 1 . . H
H17C 0.4034 1.1160 0.2510 0.108 Uiso calc R 1 . . H
H17A 0.4752 1.0870 0.3459 0.108 Uiso calc R 1 . . H
C10 0.6062(3) 0.8625(3) 0.3888(2) 0.0440(9) Uani d . 1 . . C
H10A 0.5385 0.8959 0.4003 0.053 Uiso calc R 1 . . H
C11 0.6702(3) 0.7670(4) 0.4421(2) 0.0465(9) Uani d . 1 . . C
C13 0.6316(3) 0.7175(4) 0.5163(2) 0.0714(13) Uani d . 1 . . C
H13C 0.6872 0.6527 0.5460 0.107 Uiso calc R 1 . . H
H13B 0.5525 0.6811 0.4958 0.107 Uiso calc R 1 . . H
H13A 0.6308 0.7873 0.5543 0.107 Uiso calc R 1 . . H
C12 0.7698(3) 0.7183(3) 0.4247(2) 0.0452(9) Uani d . 1 . . C
H12A 0.8134 0.6530 0.4589 0.054 Uiso calc R 1 . . H
Cl1 0.03997(9) 0.81452(10) 0.13528(7) 0.0579(4) Uani d . 1 . . Cl
O2 0.1349(3) 0.8529(3) 0.20582(18) 0.1145(13) Uani d . 1 . . O
O3 0.0506(4) 0.6872(3) 0.1139(3) 0.1540(17) Uani d . 1 . . O
O4 0.0424(3) 0.8887(3) 0.06404(17) 0.1029(11) Uani d . 1 . . O
O5 -0.0700(3) 0.8373(5) 0.1497(2) 0.1450(17) Uani d . 1 . . O
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
_geom_angle_publ_flag
C8 O1 H1 109.5 ?
C1 N1 C6 111.0(3) yes
C1 N1 C5 111.2(3) yes
C6 N1 C5 112.3(2) yes
C1 N1 H2 107.4 ?
C6 N1 H2 107.4 ?
C5 N1 H2 107.4 ?
N1 C1 C2 111.6(3) ?
N1 C1 H1A 109.3 ?
C2 C1 H1A 109.3 ?
N1 C1 H1B 109.3 ?
C2 C1 H1B 109.3 ?
H1A C1 H1B 108.0 ?
C1 C2 C3 110.7(3) ?
C1 C2 H2A 109.5 ?
C3 C2 H2A 109.5 ?
C1 C2 H2B 109.5 ?
C3 C2 H2B 109.5 ?
H2A C2 H2B 108.1 ?
C4 C3 C2 109.9(3) ?
C4 C3 H3A 109.7 ?
C2 C3 H3A 109.7 ?
C4 C3 H3B 109.7 ?
C2 C3 H3B 109.7 ?
H3A C3 H3B 108.2 ?
C5 C4 C3 111.3(3) ?
C5 C4 H4A 109.4 ?
C3 C4 H4A 109.4 ?
C5 C4 H4B 109.4 ?
C3 C4 H4B 109.4 ?
H4A C4 H4B 108.0 ?
N1 C5 C4 110.9(3) ?
N1 C5 H5A 109.5 ?
C4 C5 H5A 109.5 ?
N1 C5 H5B 109.5 ?
C4 C5 H5B 109.5 ?
H5A C5 H5B 108.0 ?
N1 C6 C7 113.0(3) ?
N1 C6 H6A 109.0 ?
C7 C6 H6A 109.0 ?
N1 C6 H6B 109.0 ?
C7 C6 H6B 109.0 ?
H6A C6 H6B 107.8 ?
C8 C7 C12 118.5(3) ?
C8 C7 C6 123.3(3) ?
C12 C7 C6 118.1(3) ?
O1 C8 C7 121.8(3) yes
O1 C8 C9 116.8(3) yes
C7 C8 C9 121.5(3) yes
C10 C9 C8 116.3(3) ?
C10 C9 C14 121.6(3) ?
C8 C9 C14 122.1(3) ?
C17 C14 C9 112.4(3) ?
C17 C14 C15 106.3(3) ?
C9 C14 C15 110.4(3) ?
C17 C14 C16 107.3(3) ?
C9 C14 C16 110.1(3) ?
C15 C14 C16 110.2(3) ?
C14 C16 H16A 109.5 ?
C14 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C14 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
C14 C15 H15A 109.5 ?
C14 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C14 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
C14 C17 H17B 109.5 ?
C14 C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
C14 C17 H17A 109.5 ?
H17B C17 H17A 109.5 ?
H17C C17 H17A 109.5 ?
C9 C10 C11 124.4(3) ?
C9 C10 H10A 117.8 ?
C11 C10 H10A 117.8 ?
C12 C11 C10 117.4(3) ?
C12 C11 C13 121.1(3) ?
C10 C11 C13 121.5(3) ?
C11 C13 H13C 109.5 ?
C11 C13 H13B 109.5 ?
H13C C13 H13B 109.5 ?
C11 C13 H13A 109.5 ?
H13C C13 H13A 109.5 ?
H13B C13 H13A 109.5 ?
C11 C12 C7 121.9(3) ?
C11 C12 H12A 119.1 ?
C7 C12 H12A 119.1 ?
O3 Cl1 O5 111.3(3) ?
O3 Cl1 O2 112.0(2) ?
O5 Cl1 O2 110.4(2) ?
O3 Cl1 O4 106.5(3) ?
O5 Cl1 O4 107.3(2) ?
O2 Cl1 O4 109.1(2) ?
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
O1 C8 . 1.378(4) yes
O1 H1 . 0.8200 ?
N1 C1 . 1.492(4) yes
N1 C6 . 1.506(4) yes
N1 C5 . 1.506(4) yes
N1 H2 . 0.9100 ?
C1 C2 . 1.512(5) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C3 . 1.516(5) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.513(5) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.511(4) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C7 . 1.503(4) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.395(4) ?
C7 C12 . 1.396(4) ?
C8 C9 . 1.408(4) ?
C9 C10 . 1.377(4) ?
C9 C14 . 1.536(4) ?
C14 C17 . 1.524(5) ?
C14 C15 . 1.537(4) ?
C14 C16 . 1.542(5) ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C17 H17A . 0.9600 ?
C10 C11 . 1.387(4) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.371(5) ?
C11 C13 . 1.512(5) ?
C13 H13C . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13A . 0.9600 ?
C12 H12A . 0.9300 ?
Cl1 O3 . 1.384(3) ?
Cl1 O5 . 1.390(3) ?
Cl1 O2 . 1.402(3) ?
Cl1 O4 . 1.411(3) ?
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
_geom_hbond_publ_flag
O1 H1 O5 1_655 0.82 2.05 2.761(4) 145 yes
N1 H2 O4 4_676 0.91 2.17 2.998(5) 151 yes
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 -178.3(3)
C5 N1 C1 C2 55.9(4)
N1 C1 C2 C3 -56.6(4)
C1 C2 C3 C4 56.4(4)
C2 C3 C4 C5 -56.7(5)
C1 N1 C5 C4 -55.5(4)
C6 N1 C5 C4 179.4(3)
C3 C4 C5 N1 56.4(4)
C1 N1 C6 C7 172.7(3)
C5 N1 C6 C7 -62.1(4)
N1 C6 C7 C8 103.7(4)
N1 C6 C7 C12 -77.9(4)
C12 C7 C8 O1 179.6(3)
C6 C7 C8 O1 -2.0(5)
C12 C7 C8 C9 -0.2(5)
C6 C7 C8 C9 178.2(3)
O1 C8 C9 C10 -178.5(3)
C7 C8 C9 C10 1.4(5)
O1 C8 C9 C14 1.8(4)
C7 C8 C9 C14 -178.3(3)
C10 C9 C14 C17 -1.1(4)
C8 C9 C14 C17 178.6(3)
C10 C9 C14 C15 -119.6(3)
C8 C9 C14 C15 60.1(4)
C10 C9 C14 C16 118.5(3)
C8 C9 C14 C16 -61.8(4)
C8 C9 C10 C11 -1.3(5)
C14 C9 C10 C11 178.5(3)
C9 C10 C11 C12 0.0(5)
C9 C10 C11 C13 -179.6(3)
C10 C11 C12 C7 1.2(5)
C13 C11 C12 C7 -179.1(3)
C8 C7 C12 C11 -1.1(5)
C6 C7 C12 C11 -179.6(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21131582
