##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_journal_date_recd_electronic     2003-09-23
_journal_date_accepted     2003-09-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2003
_journal_volume     59
_journal_issue     10
_journal_page_first     o1586
_journal_page_last     o1588
_journal_paper_category     EO
_publ_contact_author_name     'Dr Miao Du'
_publ_contact_author_address
;
College of Chemistry and Life Science
Tianjin Normal University
Tianjin 300074
People's Republic of China
;
_publ_contact_author_email     dumiao@public.tpt.tj.cn
_publ_section_title
;
2-tert-Butyl-4-methyl-6-(1-piperidiniomethyl)phenol bromide
;
loop_
    _publ_author_name
    _publ_author_address
    'Miao Du'
;
College of Chemistry and Life Science
Tianjin Normal University
Tianjin 300074
People's Republic of China
;
    'Xiao-Jun Zhao'
;
College of Chemistry and Life Science
Tianjin Normal University
Tianjin 300074
People's Republic of China
;
data_III
_chemical_name_systematic
;
2-tert-Butyl-4-methyl-6-(1-piperidiniomethyl)phenol bromide
;
_chemical_formula_moiety     'C17 H28 N O 1+, Br 1-'
_chemical_formula_sum     'C17 H28 Br N O '
_chemical_formula_iupac     'C17 H28 N O 1+, Br 1-'
_chemical_formula_weight     342.30
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     P_2ac_2ab
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     5.987(4)
_cell_length_b     12.604(8)
_cell_length_c     24.469(15)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1846(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     673
_cell_measurement_theta_min     2.32
_cell_measurement_theta_max     19.47
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'cut needle'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.232
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_F_000     720
_exptl_absorpt_coefficient_mu     2.224
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1997)'
_exptl_absorpt_correction_T_min     0.5551
_exptl_absorpt_correction_T_max     0.8082
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device     'Bruker SMART 1000'
_diffrn_measurement_method     ω
_diffrn_reflns_number     6633
_diffrn_reflns_av_R_equivalents     0.0998
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     29
_diffrn_standards_number     0
_diffrn_standards_interval_count     none
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details     Full-MATRIX
_reflns_number_total     3211
_reflns_number_gt     1809
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_R_factor_all     0.1330
_refine_ls_R_factor_gt     0.0634
_refine_ls_wR_factor_gt     0.0987
_refine_ls_wR_factor_ref     0.1224
_refine_ls_goodness_of_fit_ref     1.036
_refine_ls_restrained_S_all     1.036
_refine_ls_number_reflns     3211
_refine_ls_number_parameters     186
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.034P)²+2.308P] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.603
_refine_diff_density_min     -0.270
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983); 1305 Friedel pairs'
_refine_ls_abs_structure_Flack     0.05(3)
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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 1998)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'XP in SHELXTL (Bruker, 1998)'
_computing_publication_material     'SHELXL97'
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
    Br1 0.65975(15) 0.61668(7) 0.25746(4) 0.0589(3) Uani d . 1 . . Br
    C1 -0.1765(16) 0.9162(6) 0.2641(4) 0.056(2) Uani d . 1 . . C
    H1A -0.2670 0.8524 0.2645 0.067 Uiso calc R 1 . . H
    H1B -0.2614 0.9718 0.2463 0.067 Uiso calc R 1 . . H
    C2 -0.1217(19) 0.9495(9) 0.3229(4) 0.077(3) Uani d . 1 . . C
    H2A -0.2592 0.9589 0.3433 0.092 Uiso calc R 1 . . H
    H2B -0.0430 1.0168 0.3225 0.092 Uiso calc R 1 . . H
    C3 0.024(2) 0.8648(12) 0.3509(4) 0.088(4) Uani d . 1 . . C
    H3A 0.0611 0.8877 0.3877 0.106 Uiso calc R 1 . . H
    H3B -0.0581 0.7987 0.3535 0.106 Uiso calc R 1 . . H
    C4 0.2348(17) 0.8481(9) 0.3185(4) 0.068(3) Uani d . 1 . . C
    H4A 0.3252 0.7942 0.3362 0.082 Uiso calc R 1 . . H
    H4B 0.3201 0.9135 0.3178 0.082 Uiso calc R 1 . . H
    C5 0.1834(15) 0.8140(6) 0.2605(3) 0.050(2) Uani d . 1 . . C
    H5A 0.3215 0.8060 0.2402 0.060 Uiso calc R 1 . . H
    H5B 0.1076 0.7460 0.2609 0.060 Uiso calc R 1 . . H
    C6 -0.0192(15) 0.8619(8) 0.1744(3) 0.053(3) Uani d . 1 . . C
    H6A -0.0841 0.7914 0.1752 0.064 Uiso calc R 1 . . H
    H6B -0.1301 0.9099 0.1595 0.064 Uiso calc R 1 . . H
    C7 0.1837(16) 0.8609(7) 0.1369(3) 0.047(2) Uani d . 1 . . C
    C8 0.2533(14) 0.9549(8) 0.1115(4) 0.042(2) Uani d . 1 . . C
    C9 0.4306(15) 0.9530(7) 0.0734(4) 0.043(2) Uani d . 1 . . C
    C10 0.5328(16) 0.8546(8) 0.0639(4) 0.060(3) Uani d . 1 . . C
    H10 0.6493 0.8514 0.0389 0.072 Uiso calc R 1 . . H
    C11 0.468(2) 0.7595(9) 0.0907(4) 0.066(3) Uani d . 1 . . C
    C12 0.2910(19) 0.7648(8) 0.1250(4) 0.063(3) Uani d . 1 . . C
    H12 0.2391 0.7028 0.1412 0.076 Uiso calc R 1 . . H
    C13 0.600(2) 0.6587(8) 0.0782(5) 0.099(4) Uani d . 1 . . C
    H13A 0.7566 0.6745 0.0785 0.149 Uiso calc R 1 . . H
    H13B 0.5577 0.6322 0.0429 0.149 Uiso calc R 1 . . H
    H13C 0.5678 0.6061 0.1055 0.149 Uiso calc R 1 . . H
    C14 0.5066(15) 1.0554(8) 0.0429(4) 0.051(3) Uani d . 1 . . C
    C15 0.3083(16) 1.1059(8) 0.0127(3) 0.072(3) Uani d . 1 . . C
    H15A 0.3607 1.1635 -0.0095 0.108 Uiso calc R 1 . . H
    H15B 0.2023 1.1321 0.0389 0.108 Uiso calc R 1 . . H
    H15C 0.2379 1.0536 -0.0100 0.108 Uiso calc R 1 . . H
    C16 0.6029(17) 1.1357(8) 0.0847(4) 0.066(3) Uani d . 1 . . C
    H16A 0.7317 1.1055 0.1022 0.100 Uiso calc R 1 . . H
    H16B 0.4917 1.1517 0.1118 0.100 Uiso calc R 1 . . H
    H16C 0.6451 1.1997 0.0661 0.100 Uiso calc R 1 . . H
    C17 0.6906(18) 1.0331(8) 0.0011(4) 0.078(3) Uani d . 1 . . C
    H17A 0.7269 1.0974 -0.0179 0.116 Uiso calc R 1 . . H
    H17B 0.6395 0.9809 -0.0245 0.116 Uiso calc R 1 . . H
    H17C 0.8209 1.0071 0.0196 0.116 Uiso calc R 1 . . H
    N1 0.0368(10) 0.8959(5) 0.2328(2) 0.0408(17) Uani d . 1 . . N
    H1C 0.1145 0.9579 0.2311 0.049 Uiso calc R 1 . . H
    O1 0.1430(12) 1.0472(5) 0.1248(2) 0.0558(16) Uani d . 1 . . O
    H1 0.1887 1.0693 0.1542 0.084 Uiso calc R 1 . . H
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    C1 N1 . 1.511(8) yes
    C1 C2 . 1.533(9) yes
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C2 C3 . 1.540(11) yes
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 C4 . 1.506(11) yes
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 C5 . 1.516(12) yes
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C5 N1 . 1.514(9) yes
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C7 . 1.522(8) ?
    C6 N1 . 1.528(9) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C12 . 1.402(14) ?
    C7 C8 . 1.400(12) ?
    C8 O1 . 1.377(10) yes
    C8 C9 . 1.414(8) ?
    C9 C10 . 1.402(9) ?
    C9 C14 . 1.559(9) ?
    C10 C11 . 1.420(8) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.352(8) ?
    C11 C13 . 1.526(9) ?
    C12 H12 . 0.9300 ?
    C13 H13A . 0.9600 ?
    C13 H13B . 0.9600 ?
    C13 H13C . 0.9600 ?
    C14 C17 . 1.528(9) ?
    C14 C15 . 1.536(10) ?
    C14 C16 . 1.552(8) ?
    C15 H15A . 0.9600 ?
    C15 H15B . 0.9600 ?
    C15 H15C . 0.9600 ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    N1 H1C . 0.9100 ?
    O1 H1 . 0.8200 ?
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
    N1 C1 C2 . . 110.0(8) ?
    N1 C1 H1A . . 109.7 ?
    C2 C1 H1A . . 109.7 ?
    N1 C1 H1B . . 109.7 ?
    C2 C1 H1B . . 109.7 ?
    H1A C1 H1B . . 108.2 ?
    C1 C2 C3 . . 110.5(9) ?
    C1 C2 H2A . . 109.6 ?
    C3 C2 H2A . . 109.6 ?
    C1 C2 H2B . . 109.6 ?
    C3 C2 H2B . . 109.6 ?
    H2A C2 H2B . . 108.1 ?
    C4 C3 C2 . . 109.7(9) ?
    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 ?
    C3 C4 C5 . . 111.3(8) ?
    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 . . 110.1(7) ?
    N1 C5 H5A . . 109.6 ?
    C4 C5 H5A . . 109.6 ?
    N1 C5 H5B . . 109.6 ?
    C4 C5 H5B . . 109.6 ?
    H5A C5 H5B . . 108.2 ?
    C7 C6 N1 . . 113.0(7) ?
    C7 C6 H6A . . 109.0 ?
    N1 C6 H6A . . 109.0 ?
    C7 C6 H6B . . 109.0 ?
    N1 C6 H6B . . 109.0 ?
    H6A C6 H6B . . 107.8 ?
    C12 C7 C8 . . 120.2(9) ?
    C12 C7 C6 . . 119.9(9) ?
    C8 C7 C6 . . 119.9(9) ?
    O1 C8 C7 . . 117.9(8) yes
    O1 C8 C9 . . 122.0(8) yes
    C7 C8 C9 . . 120.1(9) yes
    C10 C9 C8 . . 116.8(9) ?
    C10 C9 C14 . . 121.7(9) ?
    C8 C9 C14 . . 121.4(9) ?
    C9 C10 C11 . . 123.4(9) ?
    C9 C10 H10 . . 118.3 ?
    C11 C10 H10 . . 118.3 ?
    C12 C11 C10 . . 117.3(10) ?
    C12 C11 C13 . . 124.8(11) ?
    C10 C11 C13 . . 117.9(11) ?
    C11 C12 C7 . . 122.0(10) ?
    C11 C12 H12 . . 119.0 ?
    C7 C12 H12 . . 119.0 ?
    C11 C13 H13A . . 109.5 ?
    C11 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C11 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C17 C14 C15 . . 108.2(8) ?
    C17 C14 C16 . . 107.0(8) ?
    C15 C14 C16 . . 109.5(8) ?
    C17 C14 C9 . . 112.2(8) ?
    C15 C14 C9 . . 110.3(7) ?
    C16 C14 C9 . . 109.4(7) ?
    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 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 C17 H17A . . 109.5 ?
    C14 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C14 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C1 N1 C5 . . 112.2(6) yes
    C1 N1 C6 . . 109.6(6) yes
    C5 N1 C6 . . 110.7(7) yes
    C1 N1 H1C . . 108.0 ?
    C5 N1 H1C . . 108.0 ?
    C6 N1 H1C . . 108.0 ?
    C8 O1 H1 . . 109.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    N1 C1 C2 C3 . . . . -56.3(10) ?
    C1 C2 C3 C4 . . . . 57.8(13) ?
    C2 C3 C4 C5 . . . . -58.5(13) ?
    C3 C4 C5 N1 . . . . 57.5(12) ?
    N1 C6 C7 C12 . . . . 100.2(10) ?
    N1 C6 C7 C8 . . . . -84.1(10) ?
    C12 C7 C8 O1 . . . . -179.8(8) ?
    C6 C7 C8 O1 . . . . 4.6(12) ?
    C12 C7 C8 C9 . . . . 0.6(13) ?
    C6 C7 C8 C9 . . . . -175.0(7) ?
    O1 C8 C9 C10 . . . . 178.9(8) ?
    C7 C8 C9 C10 . . . . -1.6(12) ?
    O1 C8 C9 C14 . . . . -1.7(12) ?
    C7 C8 C9 C14 . . . . 177.8(8) ?
    C8 C9 C10 C11 . . . . -0.3(13) ?
    C14 C9 C10 C11 . . . . -179.7(9) ?
    C9 C10 C11 C12 . . . . 3.1(15) ?
    C9 C10 C11 C13 . . . . -177.6(10) ?
    C10 C11 C12 C7 . . . . -4.0(15) ?
    C13 C11 C12 C7 . . . . 176.6(10) ?
    C8 C7 C12 C11 . . . . 2.3(14) ?
    C6 C7 C12 C11 . . . . 178.0(9) ?
    C10 C9 C14 C17 . . . . 2.9(12) ?
    C8 C9 C14 C17 . . . . -176.4(7) ?
    C10 C9 C14 C15 . . . . 123.7(9) ?
    C8 C9 C14 C15 . . . . -55.7(11) ?
    C10 C9 C14 C16 . . . . -115.8(10) ?
    C8 C9 C14 C16 . . . . 64.9(10) ?
    C2 C1 N1 C5 . . . . 56.1(9) ?
    C2 C1 N1 C6 . . . . 179.6(7) ?
    C4 C5 N1 C1 . . . . -56.4(9) ?
    C4 C5 N1 C6 . . . . -179.2(7) ?
    C7 C6 N1 C1 . . . . 168.6(7) ?
    C7 C6 N1 C5 . . . . -67.0(10) ?
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
    N1 H1C Br1 3_655 0.91 2.43 3.332(8) 170 yes
    O1 H1 Br1 3_655 0.82 2.42 3.235(9) 174 yes
