#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/60/2216038.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_2216038
loop_
_publ_author_name
'Slawin, Alexandra M. Z.'
'Harrison, William T. A.'
_publ_section_title
;
 4-(Acetylaminomethyl)-1-methylpyridinium iodide
;
_journal_coeditor_code           LH2511
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4278
_journal_page_last               o4278
_journal_paper_doi               10.1107/S1600536807046090
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C9 H13 N2 O +, I -'
_chemical_formula_moiety         'C9 H13 N2 O +, I -'
_chemical_formula_sum            'C9 H13 I N2 O'
_chemical_formula_weight         292.11
_chemical_name_systematic
;
4-(Acetylaminomethyl)-1-methylpyridinium iodide
;
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.802(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.597(2)
_cell_length_b                   12.986(3)
_cell_length_c                   10.335(3)
_cell_measurement_temperature    93(2)
_cell_volume                     1133.4(5)
_computing_cell_refinement       'CrystalClear (Rigaku, 2004)'
_computing_data_collection       'CrystalClear (Rigaku, 2004)'
_computing_data_reduction        'CrystalClear (Rigaku, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6776
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    2.793
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.817
_refine_diff_density_min         -0.458
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0203
_refine_ls_R_factor_gt           0.0188
_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)+(0.0262P)²+0.8567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0464
_refine_ls_wR_factor_ref         0.0475
_reflns_number_gt                1932
_reflns_number_total             2035
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2511.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'difmap and geom' was changed
to 'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2216038
_cod_database_fobs_code          2216038
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_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
C C1 0.1654(3) 0.42190(17) 0.5581(2) 0.0205(5) Uani d . 1
H H1 0.1710 0.3976 0.4724 0.025 Uiso calc R 1
C C2 0.0883(3) 0.36517(17) 0.6378(2) 0.0196(4) Uani d . 1
H H2A 0.0395 0.3020 0.6066 0.024 Uiso calc R 1
C C3 0.1502(3) 0.48747(17) 0.8068(2) 0.0207(5) Uani d . 1
H H3 0.1445 0.5094 0.8935 0.025 Uiso calc R 1
C C4 0.2286(3) 0.54695(17) 0.7301(2) 0.0202(5) Uani d . 1
H H4 0.2778 0.6093 0.7640 0.024 Uiso calc R 1
C C5 0.2361(2) 0.51580(16) 0.6022(2) 0.0176(4) Uani d . 1
C C6 0.3140(3) 0.57832(18) 0.5096(2) 0.0226(5) Uani d . 1
H H6A 0.3852 0.5326 0.4708 0.027 Uiso calc R 1
H H6B 0.2309 0.6033 0.4368 0.027 Uiso calc R 1
C C7 0.3626(3) 0.76363(17) 0.5334(2) 0.0200(5) Uani d . 1
C C8 0.4766(3) 0.84538(18) 0.5954(3) 0.0278(5) Uani d . 1
H H8A 0.5497 0.8161 0.6705 0.042 Uiso calc R 1
H H8B 0.4176 0.9023 0.6257 0.042 Uiso calc R 1
H H8C 0.5366 0.8711 0.5303 0.042 Uiso calc R 1
C C9 -0.0093(3) 0.33746(18) 0.8422(2) 0.0255(5) Uani d . 1
H H9A -0.0177 0.2660 0.8113 0.038 Uiso calc R 1
H H9B -0.1156 0.3668 0.8352 0.038 Uiso calc R 1
H H9C 0.0455 0.3394 0.9343 0.038 Uiso calc R 1
N N1 0.0809(2) 0.39812(12) 0.76054(19) 0.0179(4) Uani d . 1
N N2 0.4043(2) 0.66579(14) 0.5685(2) 0.0218(4) Uani d . 1
H H2 0.485(3) 0.655(2) 0.617(3) 0.026 Uiso d . 1
O O1 0.23978(19) 0.78412(13) 0.45526(17) 0.0281(4) Uani d . 1
I I1 0.753932(15) 0.602150(10) 0.806080(13) 0.01921(7) Uani d . 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
C1 0.0250(12) 0.0206(10) 0.0147(11) 0.0018(9) 0.0008(9) -0.0032(9)
C2 0.0237(11) 0.0155(10) 0.0178(11) 0.0024(9) -0.0006(9) -0.0033(9)
C3 0.0208(11) 0.0238(11) 0.0155(11) 0.0028(9) -0.0016(9) -0.0045(9)
C4 0.0203(11) 0.0170(10) 0.0212(11) 0.0014(8) -0.0020(9) -0.0068(9)
C5 0.0149(10) 0.0173(10) 0.0183(11) 0.0051(8) -0.0031(8) 0.0005(8)
C6 0.0224(12) 0.0222(10) 0.0219(12) 0.0002(9) 0.0010(10) -0.0007(9)
C7 0.0195(11) 0.0221(11) 0.0196(11) 0.0011(9) 0.0070(9) 0.0024(9)
C8 0.0269(12) 0.0206(11) 0.0360(14) -0.0033(9) 0.0061(11) 0.0019(10)
C9 0.0291(12) 0.0270(12) 0.0194(12) -0.0006(10) 0.0020(10) 0.0044(9)
N1 0.0176(10) 0.0191(9) 0.0150(10) 0.0035(7) -0.0017(8) 0.0010(7)
N2 0.0178(9) 0.0202(9) 0.0243(11) 0.0003(7) -0.0039(8) 0.0027(8)
O1 0.0246(9) 0.0277(9) 0.0300(10) 0.0024(7) 0.0002(7) 0.0102(7)
I1 0.01935(11) 0.02071(10) 0.01594(11) -0.00113(5) -0.00091(7) 0.00050(5)
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'
I I -0.4742 1.8119 '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
C2 C1 C5 120.2(2)
C2 C1 H1 119.9
C5 C1 H1 119.9
N1 C2 C1 120.6(2)
N1 C2 H2A 119.7
C1 C2 H2A 119.7
N1 C3 C4 120.8(2)
N1 C3 H3 119.6
C4 C3 H3 119.6
C3 C4 C5 120.0(2)
C3 C4 H4 120.0
C5 C4 H4 120.0
C4 C5 C1 117.8(2)
C4 C5 C6 123.5(2)
C1 C5 C6 118.7(2)
N2 C6 C5 115.13(19)
N2 C6 H6A 108.5
C5 C6 H6A 108.5
N2 C6 H6B 108.5
C5 C6 H6B 108.5
H6A C6 H6B 107.5
O1 C7 N2 122.1(2)
O1 C7 C8 122.4(2)
N2 C7 C8 115.5(2)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N1 C9 H9A 109.5
N1 C9 H9B 109.5
H9A C9 H9B 109.5
N1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C3 N1 C2 120.60(19)
C3 N1 C9 120.02(19)
C2 N1 C9 119.34(18)
C7 N2 C6 122.1(2)
C7 N2 H2 120(2)
C6 N2 H2 118(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.365(3)
C1 C5 1.400(3)
C1 H1 0.9500
C2 N1 1.352(3)
C2 H2A 0.9500
C3 N1 1.350(3)
C3 C4 1.371(3)
C3 H3 0.9500
C4 C5 1.395(3)
C4 H4 0.9500
C5 C6 1.505(3)
C6 N2 1.445(3)
C6 H6A 0.9900
C6 H6B 0.9900
C7 O1 1.232(3)
C7 N2 1.351(3)
C7 C8 1.504(3)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 N1 1.476(3)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
N2 H2 0.79(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
N2 H2 I1 . 0.79(3) 2.81(3) 3.603(2) 174(3)
C4 H4 O1 4_576 0.95 2.48 3.186(3) 131
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 C1 C2 N1 -0.8(3)
N1 C3 C4 C5 0.7(3)
C3 C4 C5 C1 -1.7(3)
C3 C4 C5 C6 177.5(2)
C2 C1 C5 C4 1.8(3)
C2 C1 C5 C6 -177.4(2)
C4 C5 C6 N2 9.8(3)
C1 C5 C6 N2 -171.05(19)
C4 C3 N1 C2 0.4(3)
C4 C3 N1 C9 -177.2(2)
C1 C2 N1 C3 -0.3(3)
C1 C2 N1 C9 177.3(2)
O1 C7 N2 C6 4.6(3)
C8 C7 N2 C6 -174.9(2)
C5 C6 N2 C7 -115.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 11186454
