##############################################################################
#                                                                            #
# 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-2014/7'
_chemical_name_systematic
;
4-Methyl-1-(3-phenoxypropyl)pyridinium bromide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H18 N O +, Br -'
_chemical_formula_sum     'C15 H18 Br N O'
_chemical_formula_structural
                                '4-methyl-1-(3-phenoxypropyl)pyridinium bromide'
_chemical_formula_iupac     'C15 H18 N O +, Br -'
_chemical_formula_weight     308.21
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P b c a'
_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _space_group_symop_operation_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'
    '-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     10.3615(3)
_cell_length_b     13.8916(6)
_cell_length_c     20.2121(8)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     2909.29(19)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     5457
_cell_measurement_theta_min     3.1690
_cell_measurement_theta_max     25.5460
_cell_measurement_temperature     295(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.19
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.407
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1264
_exptl_absorpt_coefficient_mu     2.815
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis Pro; Agilent, 2014)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.529
_exptl_absorpt_correction_T_max     1.000
_exptl_special_details     ?
_diffrn_ambient_temperature     295.0(10)
_diffrn_radiation_type     'Mo-K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type
                                   'Oxford Diffraction Xcalibur 3/Sapphire3 CCD'
_diffrn_measurement_method     'Thin slice φ and ω scans'
_diffrn_detector_area_resol_mean     16.0050
_diffrn_reflns_number     38980
_diffrn_reflns_av_R_equivalents     0.0476
_diffrn_reflns_theta_min     3.559
_diffrn_reflns_theta_max     24.999
_diffrn_reflns_theta_full     24.999
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     24
_refine_special_details     ?
_reflns_number_total     2560
_reflns_number_gt     2212
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0561
_refine_ls_R_factor_gt     0.0450
_refine_ls_wR_factor_gt     0.0827
_refine_ls_wR_factor_ref     0.0865
_refine_ls_goodness_of_fit_ref     1.199
_refine_ls_restrained_S_all     1.199
_refine_ls_number_reflns     2560
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0313P)²+1.5286P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.270
_refine_diff_density_min     -0.246
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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
;
CrysAlis PRO (Agilent, 2014)
;
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and WinGX (Farrugia, 2012)
;
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
    Br Br1 0.33702(3) 0.68529(3) 0.38455(2) 0.05802(14) Uani d 1 . .
    C C1 0.3412(3) 0.6101(2) 0.61560(14) 0.0449(7) Uani d 1 . .
    C C2 0.2231(3) 0.6169(2) 0.58402(17) 0.0497(8) Uani d 1 . .
    H H2 0.2174 0.6070 0.5386 0.060 Uiso calc 1 . .
    C C3 0.1146(4) 0.6382(3) 0.6199(2) 0.0665(10) Uani d 1 . .
    H H3 0.0352 0.6421 0.5986 0.080 Uiso calc 1 . .
    C C4 0.1213(4) 0.6540(3) 0.6864(2) 0.0768(12) Uani d 1 . .
    H H4 0.0471 0.6694 0.7101 0.092 Uiso calc 1 . .
    C C5 0.2377(4) 0.6470(3) 0.71827(19) 0.0756(11) Uani d 1 . .
    H H5 0.2422 0.6578 0.7636 0.091 Uiso calc 1 . .
    C C6 0.3494(3) 0.6241(3) 0.68326(16) 0.0567(9) Uani d 1 . .
    H H6 0.4281 0.6182 0.7050 0.068 Uiso calc 1 . .
    O O7 0.44380(18) 0.58949(16) 0.57589(10) 0.0516(6) Uani d 1 . .
    C C8 0.5707(3) 0.5894(2) 0.60379(14) 0.0487(8) Uani d 1 . .
    H H8A 0.5792 0.5381 0.6360 0.058 Uiso calc 1 . .
    H H8B 0.5880 0.6503 0.6256 0.058 Uiso calc 1 . .
    C C9 0.6631(3) 0.5744(2) 0.54734(16) 0.0514(8) Uani d 1 . .
    H H9A 0.6427 0.5145 0.5250 0.062 Uiso calc 1 . .
    H H9B 0.7504 0.5696 0.5644 0.062 Uiso calc 1 . .
    C C10 0.6554(3) 0.6566(2) 0.49855(15) 0.0478(7) Uani d 1 . .
    H H10A 0.5687 0.6602 0.4806 0.057 Uiso calc 1 . .
    H H10B 0.6732 0.7167 0.5213 0.057 Uiso calc 1 . .
    N N11 0.7491(2) 0.64405(17) 0.44343(11) 0.0400(6) Uani d 1 . .
    C C12 0.7086(3) 0.6251(2) 0.38199(15) 0.0440(7) Uani d 1 . .
    H H12 0.6206 0.6203 0.3734 0.053 Uiso calc 1 . .
    C C13 0.7952(3) 0.6126(2) 0.33169(15) 0.0469(7) Uani d 1 . .
    H H13 0.7657 0.5996 0.2892 0.056 Uiso calc 1 . .
    C C14 0.9257(3) 0.6192(2) 0.34333(15) 0.0439(7) Uani d 1 . .
    C C15 0.9652(3) 0.6400(2) 0.40727(15) 0.0500(8) Uani d 1 . .
    H H15 1.0527 0.6449 0.4169 0.060 Uiso calc 1 . .
    C C16 0.8761(3) 0.6533(2) 0.45620(16) 0.0493(8) Uani d 1 . .
    H H16 0.9033 0.6688 0.4987 0.059 Uiso calc 1 . .
    C C17 1.0219(3) 0.6050(3) 0.28885(17) 0.0680(10) Uani d 1 . .
    H H17A 1.0431 0.5379 0.2854 0.102 Uiso calc 1 . .
    H H17B 1.0986 0.6411 0.2984 0.102 Uiso calc 1 . .
    H H17C 0.9856 0.6268 0.2478 0.102 Uiso calc 1 . .
_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 O7 . 1.362(3) ?
    C1 C2 . 1.383(4) ?
    C1 C6 . 1.384(4) ?
    C2 C3 . 1.371(5) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.364(5) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.371(6) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.393(5) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    O7 C8 . 1.431(3) ?
    C8 C9 . 1.505(4) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 C10 . 1.511(4) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 N11 . 1.488(4) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    N11 C12 . 1.337(3) ?
    N11 C16 . 1.347(4) ?
    C12 C13 . 1.368(4) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.375(4) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.386(4) ?
    C14 C17 . 1.498(4) ?
    C15 C16 . 1.365(4) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 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
    O7 C1 C2 . . 115.6(3) ?
    O7 C1 C6 . . 124.3(3) ?
    C2 C1 C6 . . 120.0(3) ?
    C3 C2 C1 . . 119.8(3) ?
    C3 C2 H2 . . 120.1 ?
    C1 C2 H2 . . 120.1 ?
    C4 C3 C2 . . 120.9(4) ?
    C4 C3 H3 . . 119.5 ?
    C2 C3 H3 . . 119.5 ?
    C3 C4 C5 . . 119.8(4) ?
    C3 C4 H4 . . 120.1 ?
    C5 C4 H4 . . 120.1 ?
    C4 C5 C6 . . 120.6(3) ?
    C4 C5 H5 . . 119.7 ?
    C6 C5 H5 . . 119.7 ?
    C1 C6 C5 . . 118.9(3) ?
    C1 C6 H6 . . 120.6 ?
    C5 C6 H6 . . 120.6 ?
    C1 O7 C8 . . 119.0(2) ?
    O7 C8 C9 . . 106.6(2) ?
    O7 C8 H8A . . 110.4 ?
    C9 C8 H8A . . 110.4 ?
    O7 C8 H8B . . 110.4 ?
    C9 C8 H8B . . 110.4 ?
    H8A C8 H8B . . 108.6 ?
    C8 C9 C10 . . 110.9(3) ?
    C8 C9 H9A . . 109.5 ?
    C10 C9 H9A . . 109.5 ?
    C8 C9 H9B . . 109.5 ?
    C10 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 108.1 ?
    N11 C10 C9 . . 111.4(2) ?
    N11 C10 H10A . . 109.3 ?
    C9 C10 H10A . . 109.3 ?
    N11 C10 H10B . . 109.3 ?
    C9 C10 H10B . . 109.3 ?
    H10A C10 H10B . . 108.0 ?
    C12 N11 C16 . . 120.2(2) ?
    C12 N11 C10 . . 120.9(2) ?
    C16 N11 C10 . . 118.9(2) ?
    N11 C12 C13 . . 120.6(3) ?
    N11 C12 H12 . . 119.7 ?
    C13 C12 H12 . . 119.7 ?
    C12 C13 C14 . . 120.7(3) ?
    C12 C13 H13 . . 119.7 ?
    C14 C13 H13 . . 119.7 ?
    C13 C14 C15 . . 117.6(3) ?
    C13 C14 C17 . . 121.3(3) ?
    C15 C14 C17 . . 121.1(3) ?
    C16 C15 C14 . . 120.3(3) ?
    C16 C15 H15 . . 119.9 ?
    C14 C15 H15 . . 119.9 ?
    N11 C16 C15 . . 120.6(3) ?
    N11 C16 H16 . . 119.7 ?
    C15 C16 H16 . . 119.7 ?
    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 ?
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
    O7 C1 C2 C3 . . . . -179.4(3) ?
    C6 C1 C2 C3 . . . . 0.5(5) ?
    C1 C2 C3 C4 . . . . 0.7(5) ?
    C2 C3 C4 C5 . . . . -1.0(6) ?
    C3 C4 C5 C6 . . . . 0.0(6) ?
    O7 C1 C6 C5 . . . . 178.5(3) ?
    C2 C1 C6 C5 . . . . -1.4(5) ?
    C4 C5 C6 C1 . . . . 1.2(5) ?
    C2 C1 O7 C8 . . . . 174.7(3) ?
    C6 C1 O7 C8 . . . . -5.3(4) ?
    C1 O7 C8 C9 . . . . -174.5(3) ?
    O7 C8 C9 C10 . . . . 62.9(3) ?
    C8 C9 C10 N11 . . . . 178.4(2) ?
    C9 C10 N11 C12 . . . . 111.0(3) ?
    C9 C10 N11 C16 . . . . -69.8(3) ?
    C16 N11 C12 C13 . . . . 1.5(4) ?
    C10 N11 C12 C13 . . . . -179.3(3) ?
    N11 C12 C13 C14 . . . . 0.1(5) ?
    C12 C13 C14 C15 . . . . -0.8(5) ?
    C12 C13 C14 C17 . . . . 179.5(3) ?
    C13 C14 C15 C16 . . . . 0.0(5) ?
    C17 C14 C15 C16 . . . . 179.6(3) ?
    C12 N11 C16 C15 . . . . -2.4(5) ?
    C10 N11 C16 C15 . . . . 178.4(3) ?
    C14 C15 C16 N11 . . . . 1.6(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
    C10 H10A O7 . 0.97 2.52 2.850(3) 100
    C10 H10B Br1 4_566 0.97 2.89 3.735(3) 146
    C10 H10A Br1 . 0.97 3.11 4.043(3) 163
    C12 H12 Br1 . 0.93 3.08 3.940(3) 154
    C15 H15 Br1 1_655 0.93 3.07 3.931(3) 155
    C17 H17B Br1 1_655 0.96 3.08 3.956(4) 152
data_Global
_journal_date_recd_electronic     2017-09-22
_journal_date_accepted     2017-10-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2017
_journal_volume     73
_journal_issue     12
_journal_page_first     1831
_journal_page_last     1834
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989017015481
_journal_coeditor_code     SU5395
_publ_contact_author_name     'David L. Hughes'
_publ_contact_author_address
;
School of Chemistry
University of East Anglia
University Plain
Norwich
NR4 7TJ
United Kingdom
;
_publ_contact_author_email     'd.l.hughes@uea.ac.uk'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '+44 1 603 593 186'
_publ_section_title
;
Synthesis and crystal structure of a new pyridinium bromide salt:
4-methyl-1-(3-phenoxypropyl)pyridinium bromide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Said, Musa A.' .
;
Department of Chemistry,
Taibah University, 30002,
Al-Madina Al-Mounawara,
Saudi Arabia
;
    'Aouad, Mohamed R.' .
;
Laboratoire de Chimie & Electrochimie des Complexes Métalliques (LCECM)
 USTO-MB,
University of Sciences and Technology Mohamed Boudiaf, BP 1505 Oran,
El M'nouar,
Algeria
;
    'Hughes, David L.' .
;
School of Chemistry
University of East Anglia
University Plain
Norwich NR4 7TJ
United Kingdom
;
    'Almehmadi, Meshal A.' .
;
Department of Chemistry,
Taibah University, 30002,
Al-Madina Al-Mounawara,
Saudi Arabia
;
    'Messali, Mouslim' .
;
Department of Chemistry,
Taibah University, 30002,
Al-Madina Al-Mounawara,
Saudi Arabia
;
_publ_section_synopsis
;
The simple synthesis and crystal structure of a new pyridinium bromide salt,
4-methyl-1-(3-phenoxy propyl)pyridinium bromide, are reported. The
C--H...Br⁻ interactions have an effect on the NMR signals of the
ortho- and meta-pyridinium protons.
;
