#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/24/7202405.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7202405
loop_
_publ_author_name
'Lemmerer, Andreas'
'Bourne, Susan A.'
'Fernandes, Manuel A.'
_publ_section_title
;
 Disruption of a robust supramolecular heterosynthon in achiral
 benzylammonium and (pyridylmethyl)ammonium m-iodobenzoate salts
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              1750
_journal_paper_doi               10.1039/b811789f
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C6 H9 N2, C7 H4 I O2'
_chemical_formula_sum            'C13 H13 I N2 O2'
_chemical_formula_weight         356.15
_chemical_name_common
'((2-pyridylmethyl)ammonium) (m-iodobenzoate)'
_chemical_name_systematic
;
((2-pyridylmethyl)ammonium) (m-iodobenzoate)
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2008-06-29T12:21:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 108.452(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4778(7)
_cell_length_b                   6.0706(2)
_cell_length_c                   14.3327(5)
_cell_measurement_reflns_used    49947
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      0.41
_cell_volume                     1359.99(9)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '2.0° π and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            41513
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_min         3.29
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.351
_exptl_absorpt_correction_T_max  0.785
_exptl_absorpt_correction_T_min  0.564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.808
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0207
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0147P)²+1.6907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0465
_refine_ls_wR_factor_ref         0.0489
_reflns_number_gt                2273
_reflns_number_total             2532
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b811789f.txt
_cod_data_source_block           2_CSD_DEP_689521
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7202405
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.26671(13) 0.8389(3) 0.55956(14) 0.0169(4) Uani 1 1 d . . .
C2 C 0.20299(13) 0.7169(3) 0.49289(15) 0.0191(4) Uani 1 1 d . . .
H2 H 0.2149 0.5728 0.4748 0.023 Uiso 1 1 calc R . .
C3 C 0.12211(13) 0.8057(4) 0.45292(16) 0.0228(5) Uani 1 1 d . . .
C4 C 0.10261(14) 1.0149(4) 0.47857(18) 0.0267(5) Uani 1 1 d . . .
H4 H 0.0468 1.0744 0.4506 0.032 Uiso 1 1 calc R . .
C5 C 0.16593(15) 1.1346(4) 0.54554(18) 0.0272(5) Uani 1 1 d . . .
H5 H 0.1533 1.2772 0.5644 0.033 Uiso 1 1 calc R . .
C6 C 0.24812(14) 1.0495(4) 0.58587(16) 0.0226(5) Uani 1 1 d . . .
H6 H 0.2913 1.1347 0.6311 0.027 Uiso 1 1 calc R . .
C7 C 0.35464(13) 0.7374(3) 0.60299(15) 0.0181(4) Uani 1 1 d . . .
O1 O 0.36319(10) 0.5428(3) 0.57883(12) 0.0284(4) Uani 1 1 d . . .
O2 O 0.41254(9) 0.8534(3) 0.66072(11) 0.0239(3) Uani 1 1 d . . .
I1 I 0.029848(10) 0.61647(3) 0.348552(13) 0.03996(7) Uani 1 1 d . . .
C8 C 0.63053(13) 0.1372(3) 0.62569(15) 0.0186(4) Uani 1 1 d . . .
N2 N 0.62456(11) -0.0627(3) 0.58458(14) 0.0230(4) Uani 1 1 d . . .
C10 C 0.69349(14) -0.1939(4) 0.61527(17) 0.0263(5) Uani 1 1 d . . .
H10 H 0.6905 -0.3351 0.5858 0.032 Uiso 1 1 calc R . .
C11 C 0.76845(15) -0.1356(4) 0.68720(17) 0.0276(5) Uani 1 1 d . . .
H11 H 0.8153 -0.2349 0.7071 0.033 Uiso 1 1 calc R . .
C12 C 0.77372(14) 0.0706(4) 0.72963(17) 0.0280(5) Uani 1 1 d . . .
H12 H 0.8241 0.1155 0.7797 0.034 Uiso 1 1 calc R . .
C13 C 0.70381(14) 0.2104(4) 0.69747(16) 0.0228(5) Uani 1 1 d . . .
H13 H 0.706 0.3543 0.7242 0.027 Uiso 1 1 calc R . .
C14 C 0.55270(13) 0.2825(4) 0.58928(16) 0.0216(4) Uani 1 1 d . . .
H14A H 0.5709 0.4386 0.5939 0.026 Uiso 1 1 calc R . .
H14B H 0.5226 0.2491 0.5192 0.026 Uiso 1 1 calc R . .
N1 N 0.49304(12) 0.2503(3) 0.64698(14) 0.0181(4) Uani 1 1 d . . .
H1A H 0.4530(18) 0.347(5) 0.6284(19) 0.027 Uiso 1 1 d . . .
H1B H 0.5194(17) 0.270(4) 0.710(2) 0.027 Uiso 1 1 d . . .
H1C H 0.4671(16) 0.116(5) 0.6375(18) 0.027 Uiso 1 1 d . . .
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 0 '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 0.006 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.49(19) . . ?
C2 C1 C7 118.82(18) . . ?
C6 C1 C7 121.69(19) . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 I1 117.79(16) . . ?
C4 C3 I1 120.81(16) . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
O1 C7 O2 125.49(19) . . ?
O1 C7 C1 116.55(18) . . ?
O2 C7 C1 117.95(18) . . ?
N2 C8 C13 122.79(19) . . ?
N2 C8 C14 116.23(19) . . ?
C13 C8 C14 121.0(2) . . ?
C8 N2 C10 117.18(19) . . ?
N2 C10 C11 123.8(2) . . ?
N2 C10 H10 118.1 . . ?
C11 C10 H10 118.1 . . ?
C10 C11 C12 118.5(2) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C11 C12 C13 118.6(2) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C12 C13 C8 119.1(2) . . ?
C12 C13 H13 120.4 . . ?
C8 C13 H13 120.4 . . ?
N1 C14 C8 111.78(17) . . ?
N1 C14 H14A 109.3 . . ?
C8 C14 H14A 109.3 . . ?
N1 C14 H14B 109.3 . . ?
C8 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C14 N1 H1A 108.3(17) . . ?
C14 N1 H1B 111.0(16) . . ?
H1A N1 H1B 108(2) . . ?
C14 N1 H1C 113.4(15) . . ?
H1A N1 H1C 107(2) . . ?
H1B N1 H1C 109(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.389(3) . ?
C1 C6 1.394(3) . ?
C1 C7 1.515(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.95 . ?
C3 C4 1.388(3) . ?
C3 I1 2.105(2) . ?
C4 C5 1.380(3) . ?
C4 H4 0.95 . ?
C5 C6 1.393(3) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 O1 1.252(3) . ?
C7 O2 1.261(3) . ?
C8 N2 1.339(3) . ?
C8 C13 1.388(3) . ?
C8 C14 1.507(3) . ?
N2 C10 1.342(3) . ?
C10 C11 1.381(3) . ?
C10 H10 0.95 . ?
C11 C12 1.382(3) . ?
C11 H11 0.95 . ?
C12 C13 1.387(3) . ?
C12 H12 0.95 . ?
C13 H13 0.95 . ?
C14 N1 1.484(3) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
N1 H1A 0.86(3) . ?
N1 H1B 0.88(3) . ?
N1 H1C 0.91(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.86(3) 1.85(3) 2.713(2) 175(3) .
N1 H1B O2 0.88(3) 1.90(3) 2.774(2) 169(2) 2_646
N1 H1C O2 0.91(3) 1.91(3) 2.787(2) 161(2) 1_545
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.4(3) . . . . ?
C7 C1 C2 C3 179.53(18) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C1 C2 C3 I1 177.84(15) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
I1 C3 C4 C5 -178.41(17) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C7 C1 C6 C5 -178.74(19) . . . . ?
C2 C1 C7 O1 -3.2(3) . . . . ?
C6 C1 C7 O1 175.95(19) . . . . ?
C2 C1 C7 O2 177.54(18) . . . . ?
C6 C1 C7 O2 -3.4(3) . . . . ?
C13 C8 N2 C10 -0.3(3) . . . . ?
C14 C8 N2 C10 179.35(19) . . . . ?
C8 N2 C10 C11 1.2(3) . . . . ?
N2 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C8 1.4(3) . . . . ?
N2 C8 C13 C12 -1.0(3) . . . . ?
C14 C8 C13 C12 179.34(19) . . . . ?
N2 C8 C14 N1 89.5(2) . . . . ?
C13 C8 C14 N1 -90.9(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25934185
