#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/47/2014779.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_2014779
loop_
_publ_author_name
'Tamuly, Chandan'
'Sarma, Rupam S.'
'Batsanov, Andrei S.'
'Goeta, Andrés E.'
'Baruah, Jubaraj B.'
_publ_section_title
;
 4-[Bis(4-hydroxy-3,5-dimethylphenyl)methyl]pyridinium chloride and
 bromide
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o324
_journal_page_last               o327
_journal_paper_doi               10.1107/S0108270105008206
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C22 H24 N O2 + , Br -'
_chemical_formula_moiety         'C22 H24 N O2 + , Br -'
_chemical_formula_sum            'C22 H24 Br N O2'
_chemical_formula_weight         414.33
_chemical_melting_point          492
_chemical_name_systematic
;
4-[bis(4-hydroxy-3,5-dimethylphenyl)methyl]pyridinium bromide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 101.590(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7217(4)
_cell_length_b                   14.7461(6)
_cell_length_c                   15.4836(6)
_cell_measurement_reflns_used    5710
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.48
_cell_measurement_theta_min      2.75
_cell_volume                     1950.76(16)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2001)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source
'60W microfocus Bede Microsource with glass polycapillary optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21226
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.123
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'tetragonal prism'
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.90
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         5942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0267
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0502P)²+0.4161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0700
_reflns_number_gt                5263
_reflns_number_total             5943
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm1604.cif
_cod_data_source_block           II
_cod_depositor_comments
;
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        1950.73(14)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2014779
_cod_database_fobs_code          2014779
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Br 0.676256(14) 1.104801(8) 0.049778(8) 0.01935(5) Uani d . 1 . . Br
O1 1.53558(11) 0.67884(7) 0.30619(6) 0.02138(18) Uani d . 1 . . O
H01 1.580(2) 0.6448(14) 0.3461(13) 0.031(5) Uiso d . 1 . . H
O2 0.58366(13) 0.32722(7) 0.04327(7) 0.0261(2) Uani d . 1 . . O
H02 0.644(3) 0.2868(17) 0.0411(14) 0.043(6) Uiso d . 1 . . H
N1 0.69909(14) 0.88983(8) 0.08199(9) 0.0229(2) Uani d . 1 . . N
H1 0.666(2) 0.9386(18) 0.0574(14) 0.041(6) Uiso d . 1 . . H
C2 0.69750(15) 0.81554(9) 0.03223(9) 0.0222(2) Uani d . 1 . . C
H2 0.6602 0.8186 -0.0297 0.027 Uiso calc R 1 . . H
C3 0.75057(15) 0.73441(8) 0.07182(8) 0.0190(2) Uani d . 1 . . C
H3 0.7497 0.6813 0.0370 0.026(4) Uiso calc R 1 . . H
C4 0.80539(13) 0.73026(8) 0.16255(8) 0.0159(2) Uani d . 1 . . C
C5 0.80231(15) 0.80967(9) 0.21150(9) 0.0208(2) Uani d . 1 . . C
H5 0.8371 0.8087 0.2737 0.025 Uiso calc R 1 . . H
C6 0.74897(16) 0.88898(9) 0.16968(10) 0.0231(3) Uani d . 1 . . C
H6 0.7474 0.9431 0.2028 0.028 Uiso calc R 1 . . H
C7 0.87305(13) 0.64491(8) 0.20970(8) 0.0156(2) Uani d . 1 . . C
H7 0.8382 0.6447 0.2674 0.019 Uiso calc R 1 . . H
C11 1.37668(14) 0.66615(8) 0.28433(8) 0.0167(2) Uani d . 1 . . C
C12 1.29883(15) 0.59747(8) 0.32041(8) 0.0184(2) Uani d . 1 . . C
C13 1.13635(15) 0.59164(8) 0.29451(8) 0.0186(2) Uani d . 1 . . C
H13 1.0819 0.5462 0.3198 0.022 Uiso calc R 1 . . H
C14 1.05168(14) 0.65102(8) 0.23220(8) 0.0161(2) Uani d . 1 . . C
C15 1.13420(14) 0.71704(9) 0.19643(8) 0.0187(2) Uani d . 1 . . C
H15 1.0785 0.7571 0.1531 0.022 Uiso calc R 1 . . H
C16 1.29571(14) 0.72639(9) 0.22197(8) 0.0191(2) Uani d . 1 . . C
C17 1.38861(17) 0.53198(11) 0.38671(11) 0.0302(3) Uani d . 1 . . C
H171 1.3149 0.4932 0.4099 0.048(4) Uiso calc R 1 . . H
H172 1.4529 0.5659 0.4352 0.048(4) Uiso calc R 1 . . H
H173 1.4563 0.4942 0.3581 0.048(4) Uiso calc R 1 . . H
C18 1.38276(16) 0.79933(11) 0.18407(11) 0.0309(3) Uani d . 1 . . C
H181 1.3084 0.8362 0.1426 0.049(4) Uiso calc R 1 . . H
H182 1.4584 0.7715 0.1531 0.049(4) Uiso calc R 1 . . H
H183 1.4383 0.8379 0.2318 0.049(4) Uiso calc R 1 . . H
C21 0.66121(16) 0.40333(8) 0.08027(9) 0.0183(2) Uani d . 1 . . C
C22 0.82030(15) 0.41792(9) 0.08246(8) 0.0189(2) Uani d . 1 . . C
C23 0.89009(14) 0.49652(8) 0.12421(8) 0.0178(2) Uani d . 1 . . C
H23 0.9985 0.5068 0.1272 0.021 Uiso calc R 1 . . H
C24 0.80389(14) 0.55947(8) 0.16128(8) 0.0164(2) Uani d . 1 . . C
C25 0.64388(14) 0.54369(8) 0.15516(8) 0.0176(2) Uani d . 1 . . C
H25 0.5834 0.5873 0.1787 0.021 Uiso calc R 1 . . H
C26 0.57090(14) 0.46625(8) 0.11571(8) 0.0180(2) Uani d . 1 . . C
C27 0.91482(18) 0.35192(10) 0.04044(10) 0.0270(3) Uani d . 1 . . C
H271 0.9165 0.2929 0.0697 0.052(4) Uiso calc R 1 . . H
H272 1.0221 0.3746 0.0465 0.052(4) Uiso calc R 1 . . H
H273 0.8674 0.3453 -0.0222 0.052(4) Uiso calc R 1 . . H
C28 0.39958(16) 0.44905(10) 0.11277(10) 0.0244(3) Uani d . 1 . . C
H281 0.3583 0.4960 0.1466 0.042(3) Uiso calc R 1 . . H
H282 0.3866 0.3894 0.1383 0.042(3) Uiso calc R 1 . . H
H283 0.3425 0.4505 0.0514 0.042(3) Uiso calc R 1 . . H
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'
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
C11 O1 H01 113.5(14) ?
C21 O2 H02 110.5(16) ?
C2 N1 C6 122.65(12) yes
C2 N1 H1 118.6(15) ?
C6 N1 H1 118.8(15) ?
N1 C2 C3 119.34(13) ?
N1 C2 H2 120.3 ?
C3 C2 H2 120.3 ?
C2 C3 C4 120.19(12) ?
C2 C3 H3 119.9 ?
C4 C3 H3 119.9 ?
C3 C4 C5 118.06(11) ?
C3 C4 C7 123.03(11) ?
C5 C4 C7 118.88(11) ?
C6 C5 C4 119.98(12) ?
C6 C5 H5 120.0 ?
C4 C5 H5 120.0 ?
N1 C6 C5 119.77(12) ?
N1 C6 H6 120.1 ?
C5 C6 H6 120.1 ?
C4 C7 C24 111.83(10) yes
C4 C7 C14 109.97(10) yes
C24 C7 C14 116.38(10) yes
C4 C7 H7 106.0 ?
C24 C7 H7 106.0 ?
C14 C7 H7 106.0 ?
O1 C11 C16 115.46(11) ?
O1 C11 C12 123.25(11) ?
C16 C11 C12 121.29(11) ?
C13 C12 C11 118.48(11) ?
C13 C12 C17 120.94(12) ?
C11 C12 C17 120.57(11) ?
C12 C13 C14 121.63(12) ?
C12 C13 H13 119.2 ?
C14 C13 H13 119.2 ?
C15 C14 C13 118.00(11) ?
C15 C14 C7 122.39(11) ?
C13 C14 C7 119.52(11) ?
C14 C15 C16 122.12(11) ?
C14 C15 H15 118.9 ?
C16 C15 H15 118.9 ?
C15 C16 C11 118.46(11) ?
C15 C16 C18 121.48(12) ?
C11 C16 C18 120.06(11) ?
C12 C17 H171 109.5 ?
C12 C17 H172 109.5 ?
H171 C17 H172 109.5 ?
C12 C17 H173 109.5 ?
H171 C17 H173 109.5 ?
H172 C17 H173 109.5 ?
C16 C18 H181 109.5 ?
C16 C18 H182 109.5 ?
H181 C18 H182 109.5 ?
C16 C18 H183 109.5 ?
H181 C18 H183 109.5 ?
H182 C18 H183 109.5 ?
O2 C21 C22 122.60(12) ?
O2 C21 C26 115.88(12) ?
C22 C21 C26 121.53(11) ?
C21 C22 C23 118.32(12) ?
C21 C22 C27 121.14(12) ?
C23 C22 C27 120.53(12) ?
C24 C23 C22 121.40(12) ?
C24 C23 H23 119.3 ?
C22 C23 H23 119.3 ?
C23 C24 C25 118.43(11) ?
C23 C24 C7 124.13(11) ?
C25 C24 C7 117.44(10) ?
C26 C25 C24 121.99(11) ?
C26 C25 H25 119.0 ?
C24 C25 H25 119.0 ?
C25 C26 C21 118.29(11) ?
C25 C26 C28 121.07(12) ?
C21 C26 C28 120.63(11) ?
C22 C27 H271 109.5 ?
C22 C27 H272 109.5 ?
H271 C27 H272 109.5 ?
C22 C27 H273 109.5 ?
H271 C27 H273 109.5 ?
H272 C27 H273 109.5 ?
C26 C28 H281 109.5 ?
C26 C28 H282 109.5 ?
H281 C28 H282 109.5 ?
C26 C28 H283 109.5 ?
H281 C28 H283 109.5 ?
H282 C28 H283 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
O1 C11 . 1.3718(14) yes
O1 H01 . 0.83(2) yes
O2 C21 . 1.3746(15) yes
O2 H02 . 0.80(2) yes
N1 C2 . 1.3377(18) yes
N1 C6 . 1.340(2) yes
N1 H1 . 0.84(3) yes
C2 C3 . 1.3810(18) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.3913(17) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3981(17) ?
C4 C7 . 1.5139(17) yes
C5 C6 . 1.3720(19) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C24 . 1.5270(17) yes
C7 C14 . 1.5293(16) yes
C7 H7 . 1.0000 ?
C11 C16 . 1.3950(17) ?
C11 C12 . 1.3969(17) ?
C12 C13 . 1.3958(17) ?
C12 C17 . 1.5088(18) ?
C13 C14 . 1.3988(17) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.3903(17) ?
C15 C16 . 1.3914(17) ?
C15 H15 . 0.9500 ?
C16 C18 . 1.5022(18) ?
C17 H171 . 0.9800 ?
C17 H172 . 0.9800 ?
C17 H173 . 0.9800 ?
C18 H181 . 0.9800 ?
C18 H182 . 0.9800 ?
C18 H183 . 0.9800 ?
C21 C22 . 1.3978(18) ?
C21 C26 . 1.3986(18) ?
C22 C23 . 1.4048(17) ?
C22 C27 . 1.5053(18) ?
C23 C24 . 1.3892(17) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.3991(17) ?
C25 C26 . 1.3878(17) ?
C25 H25 . 0.9500 ?
C26 C28 . 1.5072(18) ?
C27 H271 . 0.9800 ?
C27 H272 . 0.9800 ?
C27 H273 . 0.9800 ?
C28 H281 . 0.9800 ?
C28 H282 . 0.9800 ?
C28 H283 . 0.9800 ?
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 H1 Br . 0.84(3) 2.46(3) 3.2090(11) 149.8(19)
O1 H01 Br 2_745 0.83(2) 2.47(2) 3.1984(10) 147.5(18)
O2 H02 Br 1_545 0.80(2) 2.70(2) 3.3745(10) 143(2)
C2 H2 Br 3_675 0.95 3.10 3.4576(13) 104
C7 H7 Br 2_645 1.00 2.92 3.8791(12) 161
C17 H171 Br 4_676 0.98 3.05 3.9690(15) 157
C18 H181 Br 3_775 0.98 3.13 3.8243(15) 129
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
C5 C4 C7 C14 -75.36(14)
C4 C7 C14 C15 -12.64(16)
C3 C4 C7 C24 -28.52(16)
C4 C7 C24 C25 -64.67(14)
C13 C14 C7 C24 -67.76(15)
C14 C7 C24 C23 -11.40(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133883
