##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-Methylpiperidinium bromide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C6 H14 N +, Br -'
_chemical_formula_sum     'C6 H14 Br N O0'
_chemical_formula_iupac     'C6 H14 N +, Br -'
_chemical_formula_weight     180.09
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     23.134(5)
_cell_length_b     9.997(2)
_cell_length_c     7.7214(15)
_cell_angle_alpha     90.00
_cell_angle_beta     107.90(3)
_cell_angle_gamma     90.00
_cell_volume     1699.3(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     1946
_cell_measurement_theta_min     3.0
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'Colorless'
_exptl_crystal_size_max     0.5530
_exptl_crystal_size_mid     0.4350
_exptl_crystal_size_min     0.3560
_exptl_crystal_density_diffrn     1.408
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     736
_exptl_absorpt_coefficient_mu     4.754
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrystalClear; Rigaku, 2005)'
_exptl_absorpt_correction_T_min     0.134
_exptl_absorpt_correction_T_max     0.223
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku Mercury70 CCD'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8544
_diffrn_reflns_av_R_equivalents     0.0569
_diffrn_reflns_av_sigmaI/netI     0.0461
_diffrn_reflns_theta_min     3.33
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -30
_diffrn_reflns_limit_h_max     30
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     1946
_reflns_number_gt     1327
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0738
_refine_ls_R_factor_gt     0.0425
_refine_ls_wR_factor_gt     0.0818
_refine_ls_wR_factor_ref     0.0912
_refine_ls_goodness_of_fit_ref     1.092
_refine_ls_restrained_S_all     1.092
_refine_ls_number_reflns     1946
_refine_ls_number_parameters     74
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0350P)²+0.5231P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.369
_refine_diff_density_min     -0.565
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0
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'
    'Br' 'Br' -0.2901 2.4595
                         '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'
_computing_data_collection     'SCXmini (Rigaku, 2006)'
_computing_cell_refinement     'SCXmini (Rigaku, 2006)'
_computing_data_reduction     'SCXmini (Rigaku, 2006)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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
    N N1 0.11379(15) 0.3573(3) 0.1464(4) 0.0570(9) Uani d . 1 1 . .
    H H1C 0.1188 0.4456 0.1332 0.068 Uiso d R 1 1 . .
    H H1D 0.1141 0.3431 0.2618 0.068 Uiso d R 1 1 . .
    C C1 0.16511(17) 0.2840(4) 0.1151(5) 0.0513(9) Uani d . 1 1 . .
    H H1A 0.2027 0.3117 0.2043 0.062 Uiso calc R 1 1 . .
    H H1B 0.1676 0.3057 -0.0048 0.062 Uiso calc R 1 1 . .
    C C2 0.15735(16) 0.1344(3) 0.1290(5) 0.0468(9) Uani d . 1 1 . .
    H H2 0.1575 0.1135 0.2531 0.056 Uiso calc R 1 1 . .
    C C3 0.09709(15) 0.0903(4) -0.0014(5) 0.0523(9) Uani d . 1 1 . .
    H H3A 0.0916 -0.0047 0.0134 0.063 Uiso calc R 1 1 . .
    H H3B 0.0969 0.1057 -0.1256 0.063 Uiso calc R 1 1 . .
    C C4 0.04502(18) 0.1672(4) 0.0339(6) 0.0634(11) Uani d . 1 1 . .
    H H4A 0.0070 0.1406 -0.0543 0.076 Uiso calc R 1 1 . .
    H H4B 0.0430 0.1456 0.1543 0.076 Uiso calc R 1 1 . .
    C C5 0.05371(18) 0.3159(4) 0.0204(6) 0.0641(11) Uani d . 1 1 . .
    H H5A 0.0514 0.3390 -0.1036 0.077 Uiso calc R 1 1 . .
    H H5B 0.0216 0.3632 0.0511 0.077 Uiso calc R 1 1 . .
    C C6 0.21027(17) 0.0600(4) 0.0926(6) 0.0775(13) Uani d . 1 1 . .
    H H6A 0.2043 -0.0346 0.0993 0.116 Uiso calc R 1 1 . .
    H H6B 0.2476 0.0854 0.1821 0.116 Uiso calc R 1 1 . .
    H H6C 0.2120 0.0827 -0.0265 0.116 Uiso calc R 1 1 . .
    Br Br1 0.120008(18) 0.32311(4) 0.57328(5) 0.05608(17) Uani d . 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    N1 0.091(3) 0.0367(17) 0.0462(18) -0.0022(16) 0.0255(17) 0.0003(15)
    C1 0.054(2) 0.049(2) 0.047(2) -0.0167(18) 0.0104(18) -0.0017(18)
    C2 0.053(2) 0.0416(19) 0.045(2) -0.0015(17) 0.0131(17) 0.0016(17)
    C3 0.053(2) 0.040(2) 0.061(2) -0.0077(17) 0.0138(19) -0.0038(19)
    C4 0.052(2) 0.053(2) 0.085(3) -0.0089(19) 0.020(2) 0.004(2)
    C5 0.061(3) 0.055(2) 0.074(3) 0.007(2) 0.017(2) 0.006(2)
    C6 0.059(3) 0.080(3) 0.090(3) 0.002(2) 0.017(2) -0.009(3)
    Br1 0.0834(3) 0.0399(2) 0.0459(2) -0.00318(19) 0.0213(2) -0.00200(18)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    N1 C1 . 1.477(5) ?
    N1 C5 . 1.490(5) ?
    N1 H1C . 0.9000 ?
    N1 H1D . 0.9000 ?
    C1 C2 . 1.514(5) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C2 C3 . 1.512(5) ?
    C2 C6 . 1.530(5) ?
    C2 H2 . 0.9800 ?
    C3 C4 . 1.523(5) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 C5 . 1.507(5) ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 H6A . 0.9600 ?
    C6 H6B . 0.9600 ?
    C6 H6C . 0.9600 ?
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
    C1 N1 C5 . . 113.0(3) ?
    C1 N1 H1C . . 109.3 ?
    C5 N1 H1C . . 109.0 ?
    C1 N1 H1D . . 108.7 ?
    C5 N1 H1D . . 109.0 ?
    H1C N1 H1D . . 107.8 ?
    N1 C1 C2 . . 111.1(3) ?
    N1 C1 H1A . . 109.4 ?
    C2 C1 H1A . . 109.4 ?
    N1 C1 H1B . . 109.4 ?
    C2 C1 H1B . . 109.4 ?
    H1A C1 H1B . . 108.0 ?
    C3 C2 C1 . . 110.2(3) ?
    C3 C2 C6 . . 111.2(3) ?
    C1 C2 C6 . . 110.4(3) ?
    C3 C2 H2 . . 108.3 ?
    C1 C2 H2 . . 108.3 ?
    C6 C2 H2 . . 108.3 ?
    C2 C3 C4 . . 110.6(3) ?
    C2 C3 H3A . . 109.5 ?
    C4 C3 H3A . . 109.5 ?
    C2 C3 H3B . . 109.5 ?
    C4 C3 H3B . . 109.5 ?
    H3A C3 H3B . . 108.1 ?
    C5 C4 C3 . . 110.8(3) ?
    C5 C4 H4A . . 109.5 ?
    C3 C4 H4A . . 109.5 ?
    C5 C4 H4B . . 109.5 ?
    C3 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 108.1 ?
    N1 C5 C4 . . 110.3(3) ?
    N1 C5 H5A . . 109.6 ?
    C4 C5 H5A . . 109.6 ?
    N1 C5 H5B . . 109.6 ?
    C4 C5 H5B . . 109.6 ?
    H5A C5 H5B . . 108.1 ?
    C2 C6 H6A . . 109.5 ?
    C2 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C2 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 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
    C5 N1 C1 C2 . . . . -56.3(4) ?
    N1 C1 C2 C3 . . . . 55.7(4) ?
    N1 C1 C2 C6 . . . . 178.9(3) ?
    C1 C2 C3 C4 . . . . -56.1(4) ?
    C6 C2 C3 C4 . . . . -178.8(3) ?
    C2 C3 C4 C5 . . . . 56.6(5) ?
    C1 N1 C5 C4 . . . . 56.1(4) ?
    C3 C4 C5 N1 . . . . -55.5(5) ?
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
    N1 H1D Br1 . 0.90 2.38 3.273(3) 175.0
    N1 H1C Br1 6_565 0.90 2.36 3.255(3) 173.1
_iucr_refine_instructions_details
;
TITL a in C2/c                   New: C2/c
CELL  0.71073   23.1340    9.9970    7.7214    90.000   107.900    90.000
ZERR  8           0.0050    0.0020    0.0015     0.000     0.030     0.000
LATT 7
SYMM             - X ,              Y ,    0.50000 - Z
SFAC C  H  Br N  O
UNIT 48 112 8 8 0
L.S. 20
ACTA
HTAB
HTAB N1 Br1
HTAB N1 Br1_$1
EQIV $1  x, -y+1, z-1/2
BOND $H
FMAP 2
PLAN 2
CONF
WGHT    0.035000    0.523100
FVAR       0.22469
N1    4    0.113790    0.357331    0.146421    11.00000    0.09123    0.03666 =
         0.04618    0.00031    0.02555   -0.00215
AFIX   3
H1C   2    0.118810    0.445601    0.133161    11.00000   -1.20000
H1D   2    0.114120    0.343091    0.261811    11.00000   -1.20000
AFIX   0
C1    1    0.165108    0.283975    0.115062    11.00000    0.05392    0.04932 =
         0.04731   -0.00170    0.01044   -0.01673
AFIX  23
H1A   2    0.202736    0.311746    0.204301    11.00000   -1.20000
H1B   2    0.167644    0.305736   -0.004814    11.00000   -1.20000
AFIX   0
C2    1    0.157350    0.134357    0.128959    11.00000    0.05267    0.04161 =
         0.04489    0.00156    0.01315   -0.00154
AFIX  13
H2    2    0.157487    0.113540    0.253110    11.00000   -1.20000
AFIX   0
C3    1    0.097093    0.090326   -0.001372    11.00000    0.05331    0.03956 =
         0.06148   -0.00384    0.01383   -0.00771
AFIX  23
H3A   2    0.091597   -0.004721    0.013388    11.00000   -1.20000
H3B   2    0.096942    0.105687   -0.125551    11.00000   -1.20000
AFIX   0
C4    1    0.045018    0.167245    0.033903    11.00000    0.05226    0.05258 =
         0.08473    0.00446    0.02017   -0.00894
AFIX  23
H4A   2    0.006958    0.140637   -0.054251    11.00000   -1.20000
H4B   2    0.042957    0.145585    0.154319    11.00000   -1.20000
AFIX   0
C5    1    0.053715    0.315861    0.020377    11.00000    0.06056    0.05520 =
         0.07409    0.00601    0.01689    0.00680
AFIX  23
H5A   2    0.051417    0.338999   -0.103564    11.00000   -1.20000
H5B   2    0.021593    0.363206    0.051105    11.00000   -1.20000
AFIX   0
C6    1    0.210266    0.060033    0.092575    11.00000    0.05852    0.07991 =
         0.09001   -0.00871    0.01696    0.00226
AFIX 137
H6A   2    0.204339   -0.034641    0.099265    11.00000   -1.50000
H6B   2    0.247614    0.085384    0.182120    11.00000   -1.50000
H6C   2    0.212045    0.082721   -0.026490    11.00000   -1.50000
AFIX   0
BR1   3    0.120008    0.323112    0.573280    11.00000    0.08341    0.03990 =
         0.04589   -0.00200    0.02129   -0.00318
HKLF 4
REM  a in C2/c                   New: C2/c
REM R1 =  0.0425 for   1327 Fo > 4sig(Fo)  and  0.0738 for all   1946 data
REM     74 parameters refined using      0 restraints
END
WGHT      0.0354      0.4785
REM Highest difference peak  0.369,  deepest hole -0.565,  1-sigma level  0.112
Q1    1   0.0000  0.4851 -0.2500  10.50000  0.05    0.37
Q2    1   0.0434  0.2710  0.3204  11.00000  0.05    0.32
;
data_global
_journal_date_recd_electronic     2012-04-12
_journal_date_accepted     2012-05-02
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      6
_journal_page_first     o1654
_journal_page_last     o1654
_journal_paper_category     QO
_journal_paper_doi     10.1107/S160053681201971X
_journal_coeditor_code     DS2192
_publ_contact_author_name     'Qian Xu'
_publ_contact_author_address
;
Ordered Matter Science Research Center, Southeast University, Nanjing 211189,
People's Republic of China
;
_publ_contact_author_email     'xqchem@yahoo.com.cn'
_publ_contact_author_fax     '862552090626'
_publ_contact_author_phone     '862552090626'
_publ_section_title
;
3-Methylpiperidinium bromide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Xu, Qian' .
;
Ordered Matter Science Research Center, Southeast University, Nanjing 211189,
People's Republic of China
;
