# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_I
_database_code_depnum_ccdc_archive 'CCDC 1041713'
_audit_update_record             
;
2015-01-02 deposited with the CCDC.
2015-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'[di-(3-trimethylammonium-benzoic acid)-(3-trimethylammonium-benzoate)]diiodide'
_chemical_name_common            
;
?
;
_chemical_melting_point          468
_chemical_formula_moiety         '2(C10 H14 N O2), C10 H13 N O2, 2(I)'
_chemical_formula_sum            'C30 H41 I2 N3 O6'
_chemical_formula_weight         793.46

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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'

_cell_length_a                   18.7965(10)
_cell_length_b                   13.9047(8)
_cell_length_c                   12.8843(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.010(4)
_cell_angle_gamma                90.00
_cell_volume                     3348.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7982
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      29.12

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1584
_exptl_absorpt_coefficient_mu    1.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_T_max  0.858
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (1990)).
;
_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22456
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         29.12
_reflns_number_total             7982
_reflns_number_gt                6106
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;X-Seed (Barbour, 2001) 
and POV-Ray (Persistence of Vision, 2004)

Mercury (2008)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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 > 2sigma(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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1022P)²+40.0313P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7982
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1651
_refine_ls_wR_factor_gt          0.0715
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000

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
I1 I -0.15189(3) 1.33831(6) 0.39869(5) 0.0515(2) Uani 1 1 d . . .
I2 I 0.14812(4) 1.35269(6) 0.80448(6) 0.0534(2) Uani 1 1 d . . .
C1 C 0.5139(4) 0.8793(6) 0.8189(6) 0.0276(16) Uani 1 1 d . . .
C2 C 0.5672(4) 0.8722(6) 0.9028(6) 0.0289(16) Uani 1 1 d . . .
H2 H 0.5550 0.8732 0.9709 0.035 Uiso 1 1 calc R . .
C3 C 0.6378(4) 0.8637(5) 0.8842(6) 0.0257(15) Uani 1 1 d . . .
C4 C 0.6575(5) 0.8650(6) 0.7826(6) 0.0310(17) Uani 1 1 d . . .
H4 H 0.7053 0.8610 0.7703 0.037 Uiso 1 1 calc R . .
C5 C 0.6034(4) 0.8725(5) 0.7001(5) 0.0339(18) Uani 1 1 d . . .
H5 H 0.6156 0.8730 0.6319 0.041 Uiso 1 1 calc R . .
C6 C 0.5323(4) 0.8791(6) 0.7173(6) 0.0314(17) Uani 1 1 d . . .
H6 H 0.4969 0.8834 0.6613 0.038 Uiso 1 1 calc R . .
C7 C 0.4386(5) 0.8928(7) 0.8428(6) 0.0348(18) Uani 1 1 d . . .
O1 O 0.3926(3) 0.8928(6) 0.7571(5) 0.0480(17) Uani 1 1 d . . .
H1 H 0.3538 0.9135 0.7710 0.058 Uiso 1 1 calc R . .
O2 O 0.4214(4) 0.9063(8) 0.9279(5) 0.067(3) Uani 1 1 d . . .
N1 N 0.6972(4) 0.8528(5) 0.9698(6) 0.0315(15) Uani 1 1 d . . .
C8 C 0.6687(6) 0.8520(9) 1.0753(7) 0.050(3) Uani 1 1 d . . .
H81 H 0.6361 0.7992 1.0786 0.075 Uiso 1 1 calc R . .
H82 H 0.6442 0.9113 1.0852 0.075 Uiso 1 1 calc R . .
H83 H 0.7078 0.8449 1.1290 0.075 Uiso 1 1 calc R . .
C9 C 0.7367(6) 0.7606(9) 0.9556(9) 0.060(3) Uani 1 1 d . . .
H91 H 0.7548 0.7607 0.8886 0.090 Uiso 1 1 calc R . .
H92 H 0.7048 0.7072 0.9598 0.090 Uiso 1 1 calc R . .
H93 H 0.7759 0.7550 1.0094 0.090 Uiso 1 1 calc R . .
C10 C 0.7480(4) 0.9370(5) 0.9697(5) 0.066(3) Uani 1 1 d R . .
H101 H 0.7673 0.9401 0.9037 0.099 Uiso 1 1 calc R . .
H102 H 0.7862 0.9289 1.0246 0.099 Uiso 1 1 calc R . .
H103 H 0.7227 0.9955 0.9808 0.099 Uiso 1 1 calc R . .
C11 C 0.1553(4) 1.0187(6) 0.7271(8) 0.0354(19) Uani 1 1 d . . .
C12 C 0.1163(5) 1.0838(7) 0.6588(8) 0.041(2) Uani 1 1 d . . .
H12 H 0.1373 1.1147 0.6057 0.050 Uiso 1 1 calc R . .
C13 C 0.0447(5) 1.0999(7) 0.6745(8) 0.041(2) Uani 1 1 d . . .
C14 C 0.0137(6) 1.0545(9) 0.7531(11) 0.062(3) Uani 1 1 d . . .
H14 H -0.0344 1.0654 0.7603 0.074 Uiso 1 1 calc R . .
C15 C 0.0533(6) 0.9917(9) 0.8227(11) 0.066(4) Uani 1 1 d . . .
H15 H 0.0323 0.9628 0.8771 0.080 Uiso 1 1 calc R . .
C16 C 0.1244(6) 0.9742(8) 0.8083(9) 0.053(3) Uani 1 1 d . . .
H16 H 0.1514 0.9325 0.8531 0.063 Uiso 1 1 calc R . .
C17 C 0.2345(4) 1.0048(6) 0.7168(7) 0.0333(18) Uani 1 1 d . . .
O11 O 0.2660(3) 0.9449(5) 0.7783(6) 0.0466(17) Uani 1 1 d . . .
O12 O 0.2622(3) 1.0559(5) 0.6532(6) 0.0476(17) Uani 1 1 d . . .
N11 N -0.0004(4) 1.1672(6) 0.6032(7) 0.0438(19) Uani 1 1 d . . .
C18 C 0.0436(7) 1.2325(10) 0.5394(10) 0.068(4) Uani 1 1 d . . .
H181 H 0.0710 1.1939 0.4962 0.101 Uiso 1 1 calc R . .
H182 H 0.0754 1.2708 0.5856 0.101 Uiso 1 1 calc R . .
H183 H 0.0122 1.2738 0.4961 0.101 Uiso 1 1 calc R . .
C19 C -0.0522(8) 1.1106(11) 0.5319(15) 0.099(6) Uani 1 1 d . . .
H191 H -0.0799 1.0697 0.5724 0.148 Uiso 1 1 calc R . .
H192 H -0.0266 1.0718 0.4866 0.148 Uiso 1 1 calc R . .
H193 H -0.0836 1.1537 0.4908 0.148 Uiso 1 1 calc R . .
C20 C -0.0406(6) 1.2369(8) 0.6665(10) 0.056(3) Uani 1 1 d . . .
H201 H -0.0702 1.2016 0.7095 0.084 Uiso 1 1 calc R . .
H202 H -0.0701 1.2780 0.6201 0.084 Uiso 1 1 calc R . .
H203 H -0.0070 1.2753 0.7099 0.084 Uiso 1 1 calc R . .
C21 C 0.5105(4) 1.1204(6) 0.6824(6) 0.0256(15) Uani 1 1 d . . .
C22 C 0.5628(4) 1.1292(6) 0.6143(6) 0.0276(16) Uani 1 1 d . . .
H22 H 0.5502 1.1300 0.5426 0.033 Uiso 1 1 calc R . .
C23 C 0.6340(4) 1.1369(5) 0.6541(6) 0.0269(15) Uani 1 1 d . . .
C24 C 0.6543(5) 1.1341(6) 0.7605(6) 0.0336(18) Uani 1 1 d . . .
H24 H 0.7024 1.1381 0.7858 0.040 Uiso 1 1 calc R . .
C25 C 0.6022(5) 1.1254(7) 0.8295(7) 0.0353(18) Uani 1 1 d . . .
H25 H 0.6154 1.1233 0.9011 0.042 Uiso 1 1 calc R . .
C26 C 0.5308(4) 1.1199(6) 0.7907(6) 0.0298(16) Uani 1 1 d . . .
H26 H 0.4959 1.1159 0.8366 0.036 Uiso 1 1 calc R . .
C27 C 0.4340(5) 1.1078(7) 0.6399(7) 0.0351(18) Uani 1 1 d . . .
O21 O 0.3894(3) 1.1077(6) 0.7106(5) 0.0464(16) Uani 1 1 d . . .
H21 H 0.3517 1.0826 0.6868 0.070 Uiso 1 1 calc R . .
O22 O 0.4175(4) 1.0944(8) 0.5480(6) 0.072(3) Uani 1 1 d . . .
N21 N 0.6919(4) 1.1480(5) 0.5833(5) 0.0307(15) Uani 1 1 d . . .
C28 C 0.6630(5) 1.1506(8) 0.4700(7) 0.046(2) Uani 1 1 d . . .
H281 H 0.6381 1.0917 0.4518 0.070 Uiso 1 1 calc R . .
H282 H 0.7018 1.1580 0.4278 0.070 Uiso 1 1 calc R . .
H283 H 0.6306 1.2038 0.4580 0.070 Uiso 1 1 calc R . .
C29 C 0.7315(6) 1.2410(8) 0.6109(9) 0.052(3) Uani 1 1 d . . .
H291 H 0.7502 1.2398 0.6832 0.078 Uiso 1 1 calc R . .
H292 H 0.6993 1.2943 0.5987 0.078 Uiso 1 1 calc R . .
H293 H 0.7703 1.2478 0.5684 0.078 Uiso 1 1 calc R . .
C30 C 0.7425(6) 1.0648(8) 0.5984(9) 0.054(3) Uani 1 1 d . . .
H301 H 0.7172 1.0061 0.5809 0.080 Uiso 1 1 calc R . .
H302 H 0.7627 1.0624 0.6699 0.080 Uiso 1 1 calc R . .
H303 H 0.7801 1.0726 0.5541 0.080 Uiso 1 1 calc R . .



_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C3 1.493(10) . ?
N1 C9 1.503(13) . ?
N1 C10 1.510(10) . ?
N1 C8 1.512(12) . ?
C7 O2 1.190(11) . ?
C7 O1 1.329(10) . ?
C7 C1 1.492(12) . ?
C3 C2 1.378(11) . ?
C3 C4 1.398(11) . ?
C1 C6 1.389(11) . ?
C1 C2 1.398(10) . ?
C6 C5 1.381(11) . ?
C4 C5 1.395(10) . ?
N21 C23 1.499(10) . ?
N21 C30 1.497(12) . ?
N21 C28 1.504(12) . ?
N21 C29 1.517(11) . ?
C27 O22 1.206(11) . ?
C27 O21 1.301(10) . ?
C27 C21 1.494(11) . ?
C23 C22 1.386(11) . ?
C23 C24 1.384(11) . ?
C24 C25 1.395(12) . ?
C25 C26 1.386(12) . ?
C21 C22 1.391(11) . ?
C21 C26 1.407(11) . ?
C16 C11 1.395(14) . ?
C16 C15 1.390(15) . ?
O12 C17 1.240(11) . ?
C17 O11 1.255(10) . ?
C17 C11 1.520(11) . ?
C20 N11 1.519(13) . ?
C13 C14 1.374(15) . ?
C13 C12 1.399(13) . ?
C13 N11 1.509(12) . ?
C12 C11 1.413(12) . ?
C18 N11 1.526(15) . ?
C15 C14 1.407(16) . ?
N11 C19 1.491(15) . ?

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
C3 N1 C9 109.8(7) . . ?
C3 N1 C10 110.2(6) . . ?
C9 N1 C10 109.9(7) . . ?
C3 N1 C8 110.9(7) . . ?
C9 N1 C8 109.2(8) . . ?
C10 N1 C8 106.8(7) . . ?
O2 C7 O1 123.4(9) . . ?
O2 C7 C1 124.4(8) . . ?
O1 C7 C1 112.2(7) . . ?
C2 C3 C4 121.1(7) . . ?
C2 C3 N1 122.7(7) . . ?
C4 C3 N1 116.2(7) . . ?
C6 C1 C2 120.0(7) . . ?
C6 C1 C7 122.0(7) . . ?
C2 C1 C7 117.9(7) . . ?
C5 C6 C1 119.5(7) . . ?
C3 C2 C1 119.8(7) . . ?
C5 C4 C3 118.1(7) . . ?
C6 C5 C4 121.5(7) . . ?
C23 N21 C30 109.5(7) . . ?
C23 N21 C28 112.5(7) . . ?
C30 N21 C28 107.8(8) . . ?
C23 N21 C29 108.4(7) . . ?
C30 N21 C29 109.8(8) . . ?
C28 N21 C29 109.0(8) . . ?
O22 C27 O21 124.7(8) . . ?
O22 C27 C21 121.1(8) . . ?
O21 C27 C21 114.1(7) . . ?
C22 C23 C24 121.3(8) . . ?
C22 C23 N21 121.1(7) . . ?
C24 C23 N21 117.6(7) . . ?
C23 C24 C25 119.6(8) . . ?
C26 C25 C24 119.6(8) . . ?
C22 C21 C26 119.3(7) . . ?
C22 C21 C27 119.7(7) . . ?
C26 C21 C27 120.9(7) . . ?
C23 C22 C21 119.5(7) . . ?
C25 C26 C21 120.6(7) . . ?
C11 C16 C15 120.3(10) . . ?
O12 C17 O11 126.4(8) . . ?
O12 C17 C11 117.9(7) . . ?
O11 C17 C11 115.6(8) . . ?
C14 C13 C12 121.5(9) . . ?
C14 C13 N11 118.6(8) . . ?
C12 C13 N11 119.9(9) . . ?
C13 C12 C11 117.2(9) . . ?
C16 C11 C12 121.4(8) . . ?
C16 C11 C17 119.9(8) . . ?
C12 C11 C17 118.5(8) . . ?
C16 C15 C14 118.4(10) . . ?
C13 C14 C15 121.2(9) . . ?
C19 N11 C13 109.7(9) . . ?
C19 N11 C20 109.8(10) . . ?
C13 N11 C20 110.4(8) . . ?
C19 N11 C18 109.8(11) . . ?
C13 N11 C18 113.3(8) . . ?
C20 N11 C18 103.8(9) . . ?

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
C9 N1 C3 C2 121.1(9) . . . . ?
C10 N1 C3 C2 -117.7(8) . . . . ?
C8 N1 C3 C2 0.4(11) . . . . ?
C9 N1 C3 C4 -59.0(10) . . . . ?
C10 N1 C3 C4 62.2(9) . . . . ?
C8 N1 C3 C4 -179.7(8) . . . . ?
O2 C7 C1 C6 -169.5(10) . . . . ?
O1 C7 C1 C6 7.3(12) . . . . ?
O2 C7 C1 C2 6.9(15) . . . . ?
O1 C7 C1 C2 -176.3(8) . . . . ?
C2 C1 C6 C5 -0.5(12) . . . . ?
C7 C1 C6 C5 175.9(8) . . . . ?
C4 C3 C2 C1 2.0(12) . . . . ?
N1 C3 C2 C1 -178.2(7) . . . . ?
C6 C1 C2 C3 -0.9(12) . . . . ?
C7 C1 C2 C3 -177.3(8) . . . . ?
C2 C3 C4 C5 -1.8(12) . . . . ?
N1 C3 C4 C5 178.4(7) . . . . ?
C1 C6 C5 C4 0.6(12) . . . . ?
C3 C4 C5 C6 0.5(12) . . . . ?
C30 N21 C23 C22 -119.1(9) . . . . ?
C28 N21 C23 C22 0.7(11) . . . . ?
C29 N21 C23 C22 121.3(9) . . . . ?
C30 N21 C23 C24 60.6(10) . . . . ?
C28 N21 C23 C24 -179.6(8) . . . . ?
C29 N21 C23 C24 -59.0(10) . . . . ?
C22 C23 C24 C25 -1.3(13) . . . . ?
N21 C23 C24 C25 179.0(8) . . . . ?
C23 C24 C25 C26 -0.2(13) . . . . ?
O22 C27 C21 C22 8.4(14) . . . . ?
O21 C27 C21 C22 -175.0(8) . . . . ?
O22 C27 C21 C26 -169.3(10) . . . . ?
O21 C27 C21 C26 7.3(12) . . . . ?
C24 C23 C22 C21 1.2(12) . . . . ?
N21 C23 C22 C21 -179.1(7) . . . . ?
C26 C21 C22 C23 0.3(12) . . . . ?
C27 C21 C22 C23 -177.4(8) . . . . ?
C24 C25 C26 C21 1.8(13) . . . . ?
C22 C21 C26 C25 -1.8(13) . . . . ?
C27 C21 C26 C25 175.8(8) . . . . ?
C14 C13 C12 C11 0.1(16) . . . . ?
N11 C13 C12 C11 -178.9(8) . . . . ?
C15 C16 C11 C12 1.3(17) . . . . ?
C15 C16 C11 C17 175.5(11) . . . . ?
C13 C12 C11 C16 -1.6(15) . . . . ?
C13 C12 C11 C17 -175.9(9) . . . . ?
O12 C17 C11 C16 -169.9(10) . . . . ?
O11 C17 C11 C16 6.7(13) . . . . ?
O12 C17 C11 C12 4.5(13) . . . . ?
O11 C17 C11 C12 -178.9(9) . . . . ?
C11 C16 C15 C14 1(2) . . . . ?
C12 C13 C14 C15 1.7(19) . . . . ?
N11 C13 C14 C15 -179.3(12) . . . . ?
C16 C15 C14 C13 -2(2) . . . . ?
C14 C13 N11 C19 -72.4(14) . . . . ?
C12 C13 N11 C19 106.7(13) . . . . ?
C14 C13 N11 C20 48.8(13) . . . . ?
C12 C13 N11 C20 -132.2(10) . . . . ?
C14 C13 N11 C18 164.6(11) . . . . ?
C12 C13 N11 C18 -16.3(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.888
_diffrn_reflns_theta_full        29.12
_diffrn_measured_fraction_theta_full 0.888
_refine_diff_density_max         5.893
_refine_diff_density_min         -1.560
_refine_diff_density_rms         0.206
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_II
_database_code_depnum_ccdc_archive 'CCDC 1041714'
_audit_update_record             
;
2015-01-02 deposited with the CCDC.
2015-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'[di-(3-trimethylammonium-benzoic acid)-(3-trimethylammonium-benzoate)]diiodide'
_chemical_name_common            
;
?
;
_chemical_melting_point          459
_chemical_formula_moiety         '2(C10 H14 N O2), C10 H13 N O2, 2(I)'
_chemical_formula_sum            'C30 H41 I2 N3 O6'
_chemical_formula_weight         793.46

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pccn
_symmetry_space_group_name_Hall  '-P 2ab 2ac'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   37.3738(17)
_cell_length_b                   13.9167(11)
_cell_length_c                   12.8674(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6692.6(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7338
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      27.91

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3168
_exptl_absorpt_coefficient_mu    1.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.625
_exptl_absorpt_correction_T_max  0.809
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (1990)).
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16812
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0814
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         27.91
_reflns_number_total             7338
_reflns_number_gt                3911
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;X-Seed (Barbour, 2001) 
and POV-Ray (Persistence of Vision, 2004)

Mercury (2008)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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 > 2sigma(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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0193P)²+6.7756P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7338
_refine_ls_number_parameters     372
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1384
_refine_ls_R_factor_gt           0.0639
_refine_ls_wR_factor_ref         0.1033
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
I1 I -0.075759(11) 0.33934(3) 0.41953(3) 0.05460(15) Uani 1 1 d . . .
I2 I 0.073852(11) 0.35432(3) 0.78537(3) 0.05848(16) Uani 1 1 d . . .
C1 C 0.25588(13) -0.1199(4) 0.7428(4) 0.0275(13) Uani 1 1 d . . .
C2 C 0.28143(13) -0.1288(4) 0.8206(4) 0.0286(13) Uani 1 1 d . . .
H2 H 0.2748 -0.1292 0.8903 0.034 Uiso 1 1 calc R . .
C3 C 0.31689(13) -0.1372(4) 0.7918(4) 0.0265(12) Uani 1 1 d . . .
C4 C 0.32688(14) -0.1339(4) 0.6891(4) 0.0352(14) Uani 1 1 d . . .
H4 H 0.3509 -0.1374 0.6708 0.042 Uiso 1 1 calc . . .
C5 C 0.30101(11) -0.1253(3) 0.6133(3) 0.0388(15) Uani 1 1 d . . .
H5 H 0.3076 -0.1242 0.5436 0.047 Uiso 1 1 calc R . .
C6 C 0.26592(11) -0.1184(3) 0.6401(3) 0.0354(14) Uani 1 1 d R . .
H6 H 0.2485 -0.1127 0.5887 0.042 Uiso 1 1 d R . .
C7 C 0.21740(14) -0.1055(4) 0.7750(5) 0.0331(14) Uani 1 1 d . . .
O1 O 0.19527(9) -0.1069(3) 0.6971(3) 0.0480(11) Uani 1 1 d . . .
H1 H 0.1760 -0.0845 0.7153 0.058 Uiso 1 1 calc R . .
O2 O 0.20881(10) -0.0939(4) 0.8644(3) 0.0642(15) Uani 1 1 d . . .
N1 N 0.34585(11) -0.1490(3) 0.8721(3) 0.0319(11) Uani 1 1 d . . .
C8 C 0.33162(16) -0.1528(5) 0.9799(4) 0.0556(19) Uani 1 1 d G . .
H81 H 0.3153 -0.2059 0.9840 0.083 Uiso 1 1 d G . .
H82 H 0.3196 -0.0949 1.0002 0.083 Uiso 1 1 d G . .
H83 H 0.3515 -0.1641 1.0255 0.083 Uiso 1 1 d G . .
C9 C 0.36581(17) -0.2403(5) 0.8505(5) 0.0565(19) Uani 1 1 d G . .
H91 H 0.3480 -0.2898 0.8551 0.085 Uiso 1 1 d G . .
H92 H 0.3837 -0.2506 0.9028 0.085 Uiso 1 1 d G . .
H93 H 0.3767 -0.2420 0.7830 0.085 Uiso 1 1 d G . .
C10 C 0.37127(17) -0.0654(5) 0.8651(6) 0.062(2) Uani 1 1 d G . .
H101 H 0.3897 -0.0770 0.9156 0.093 Uiso 1 1 d G . .
H102 H 0.3587 -0.0075 0.8825 0.093 Uiso 1 1 d G . .
H103 H 0.3819 -0.0588 0.7975 0.093 Uiso 1 1 d G . .
C11 C 0.07799(13) 0.0232(4) 0.7027(4) 0.0323(13) Uani 1 1 d . . .
C12 C 0.05822(13) 0.0867(4) 0.6427(4) 0.0344(14) Uani 1 1 d . . .
H12 H 0.0689 0.1183 0.5871 0.041 Uiso 1 1 calc R . .
C13 C 0.02262(13) 0.1031(4) 0.6659(4) 0.0343(14) Uani 1 1 d . . .
C14 C 0.00677(16) 0.0563(4) 0.7477(5) 0.0540(19) Uani 1 1 d . . .
H14 H -0.0173 0.0670 0.7621 0.065 Uiso 1 1 calc R . .
C15 C 0.02611(16) -0.0062(5) 0.8087(6) 0.066(2) Uani 1 1 d . . .
H15 H 0.0154 -0.0366 0.8651 0.079 Uiso 1 1 calc R . .
C16 C 0.06204(16) -0.0237(4) 0.7850(5) 0.0524(18) Uani 1 1 d . . .
H16 H 0.0752 -0.0668 0.8248 0.063 Uiso 1 1 calc R . .
C17 C 0.11740(13) 0.0073(4) 0.6815(5) 0.0339(14) Uani 1 1 d . . .
O11 O 0.13290(10) -0.0547(3) 0.7362(3) 0.0517(12) Uani 1 1 d . . .
O12 O 0.13191(10) 0.0593(3) 0.6151(3) 0.0494(12) Uani 1 1 d . . .
N11 N 0.00046(11) 0.1704(3) 0.6018(4) 0.0421(13) Uani 1 1 d G . .
C18 C 0.02216(17) 0.2349(5) 0.5333(5) 0.067(2) Uani 1 1 d G . .
H181 H 0.0368 0.2022 0.4834 0.100 Uiso 1 1 d G . .
H182 H 0.0371 0.2716 0.5793 0.100 Uiso 1 1 d G . .
H183 H 0.0060 0.2772 0.4978 0.100 Uiso 1 1 d G . .
C19 C -0.02437(17) 0.1141(4) 0.5339(6) 0.097(3) Uani 1 1 d G . .
H191 H -0.0107 0.0777 0.4845 0.146 Uiso 1 1 d G . .
H192 H -0.0401 0.1573 0.4977 0.146 Uiso 1 1 d G . .
H193 H -0.0383 0.0711 0.5760 0.146 Uiso 1 1 d G . .
C20 C -0.02083(18) 0.2364(5) 0.6702(5) 0.064(2) Uani 1 1 d G . .
H201 H -0.0051 0.2684 0.7181 0.096 Uiso 1 1 d G . .
H202 H -0.0383 0.2001 0.7083 0.096 Uiso 1 1 d G . .
H203 H -0.0327 0.2833 0.6277 0.096 Uiso 1 1 d G . .
C21 C 0.25702(14) 0.1210(4) 0.6090(4) 0.0318(13) Uani 1 1 d . . .
C22 C 0.28363(14) 0.1278(4) 0.5341(4) 0.0313(13) Uani 1 1 d . . .
H22 H 0.2777 0.1267 0.4639 0.038 Uiso 1 1 calc R . .
C23 C 0.31885(14) 0.1361(4) 0.5638(4) 0.0272(13) Uani 1 1 d . . .
C24 C 0.32809(15) 0.1340(4) 0.6679(4) 0.0369(15) Uani 1 1 d . . .
H24 H 0.3520 0.1375 0.6874 0.044 Uiso 1 1 calc R . .
C25 C 0.30198(15) 0.1267(4) 0.7420(4) 0.0394(15) Uani 1 1 d . . .
H25 H 0.3082 0.1253 0.8120 0.047 Uiso 1 1 calc R . .
C26 C 0.26642(14) 0.1215(4) 0.7132(4) 0.0345(14) Uani 1 1 d . . .
H26 H 0.2487 0.1183 0.7638 0.041 Uiso 1 1 calc R . .
C27 C 0.21933(15) 0.1083(5) 0.5748(5) 0.0385(15) Uani 1 1 d . . .
O21 O 0.19636(10) 0.1086(3) 0.6519(3) 0.0513(12) Uani 1 1 d . . .
H21 H 0.1768 0.0902 0.6309 0.062 Uiso 1 1 calc R . .
O22 O 0.21114(10) 0.0954(4) 0.4862(3) 0.0716(16) Uani 1 1 d . . .
N21 N 0.34843(11) 0.1460(3) 0.4859(3) 0.0332(11) Uani 1 1 d . . .
C28 C 0.33512(17) 0.1491(5) 0.3768(4) 0.0542(19) Uani 1 1 d G . .
H281 H 0.3225 0.0916 0.3576 0.081 Uiso 1 1 d G . .
H282 H 0.3557 0.1567 0.3329 0.081 Uiso 1 1 d G . .
H283 H 0.3196 0.2035 0.3687 0.081 Uiso 1 1 d G . .
C29 C 0.36830(19) 0.2384(5) 0.5064(6) 0.067(2) Uani 1 1 d G . .
H291 H 0.3515 0.2904 0.5007 0.100 Uiso 1 1 d G . .
H292 H 0.3864 0.2450 0.4539 0.100 Uiso 1 1 d G . .
H293 H 0.3793 0.2397 0.5738 0.100 Uiso 1 1 d G . .
C30 C 0.37359(19) 0.0622(5) 0.4955(6) 0.070(2) Uani 1 1 d G . .
H301 H 0.3612 0.0040 0.4782 0.106 Uiso 1 1 d G . .
H302 H 0.3849 0.0552 0.5621 0.106 Uiso 1 1 d G . .
H303 H 0.3914 0.0752 0.4437 0.106 Uiso 1 1 d G . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.300(6) . ?
O1 H1 0.8200 . ?
O2 C7 1.204(6) . ?
N1 C8 1.487(6) . ?
N1 C9 1.500(7) . ?
N1 C10 1.504(7) . ?
N1 C3 1.506(6) . ?
C1 C6 1.374(6) . ?
C1 C2 1.390(6) . ?
C1 C7 1.510(7) . ?
C2 C3 1.381(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(7) . ?
C4 C5 1.378(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.3592 . ?
C5 H5 0.9300 . ?
C6 H6 0.9302 . ?
C10 H101 0.9601 . ?
C10 H102 0.9599 . ?
C10 H103 0.9601 . ?
C8 H81 0.9600 . ?
C8 H82 0.9598 . ?
C8 H83 0.9602 . ?
C9 H91 0.9602 . ?
C9 H92 0.9598 . ?
C9 H93 0.9599 . ?
O11 C17 1.256(6) . ?
O12 C17 1.243(6) . ?
C11 C16 1.380(7) . ?
C11 C12 1.387(7) . ?
C11 C17 1.514(7) . ?
C12 C13 1.382(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(8) . ?
C13 N11 1.498(7) . ?
C14 C15 1.378(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.398(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C20 N11 1.501(7) . ?
C20 H201 0.9597 . ?
C20 H202 0.9601 . ?
C20 H203 0.9602 . ?
C18 N11 1.497(7) . ?
C18 H181 0.9601 . ?
C18 H182 0.9600 . ?
C18 H183 0.9600 . ?
N11 C19 1.4963 1 ?
N11 C19 1.4963 . ?
C19 C19 0.000(14) 1 ?
C19 H191 0.9600 . ?
C19 H192 0.9601 . ?
C19 H193 0.9601 . ?
O21 C27 1.312(6) . ?
O21 H21 0.8200 . ?
O22 C27 1.194(6) . ?
N21 C28 1.490(6) . ?
N21 C23 1.498(6) . ?
N21 C30 1.502(7) . ?
N21 C29 1.509(7) . ?
C21 C26 1.385(7) . ?
C21 C22 1.389(7) . ?
C21 C27 1.487(7) . ?
C22 C23 1.376(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(7) . ?
C24 C25 1.369(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.382(7) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C30 H301 0.9599 . ?
C30 H302 0.9600 . ?
C30 H303 0.9599 . ?
C28 H281 0.9600 . ?
C28 H282 0.9598 . ?
C28 H283 0.9603 . ?
C29 H291 0.9600 . ?
C29 H292 0.9600 . ?
C29 H293 0.9600 . ?

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
C7 O1 H1 109.5 . . ?
C8 N1 C9 108.7(5) . . ?
C8 N1 C10 108.1(5) . . ?
C9 N1 C10 109.3(5) . . ?
C8 N1 C3 112.8(4) . . ?
C9 N1 C3 108.8(4) . . ?
C10 N1 C3 109.2(4) . . ?
C6 C1 C2 120.5(5) . . ?
C6 C1 C7 121.5(4) . . ?
C2 C1 C7 117.9(5) . . ?
C3 C2 C1 118.2(5) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C4 C3 C2 121.1(5) . . ?
C4 C3 N1 117.9(4) . . ?
C2 C3 N1 120.9(5) . . ?
C3 C4 C5 119.5(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 119.6 . . ?
O2 C7 O1 124.7(5) . . ?
O2 C7 C1 122.3(5) . . ?
O1 C7 C1 113.0(5) . . ?
N1 C10 H101 106.4 . . ?
N1 C10 H102 109.0 . . ?
H101 C10 H102 109.5 . . ?
N1 C10 H103 112.9 . . ?
H101 C10 H103 109.5 . . ?
H102 C10 H103 109.5 . . ?
N1 C8 H81 107.8 . . ?
N1 C8 H82 113.1 . . ?
H81 C8 H82 109.5 . . ?
N1 C8 H83 107.4 . . ?
H81 C8 H83 109.5 . . ?
H82 C8 H83 109.5 . . ?
N1 C9 H91 104.6 . . ?
N1 C9 H92 110.1 . . ?
H91 C9 H92 109.5 . . ?
N1 C9 H93 113.6 . . ?
H91 C9 H93 109.5 . . ?
H92 C9 H93 109.5 . . ?
C16 C11 C12 119.9(5) . . ?
C16 C11 C17 119.3(5) . . ?
C12 C11 C17 120.8(5) . . ?
C13 C12 C11 119.9(5) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 120.2(5) . . ?
C14 C13 N11 118.7(5) . . ?
C12 C13 N11 121.1(5) . . ?
C13 C14 C15 120.7(6) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C16 119.3(6) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C15 120.1(6) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
O12 C17 O11 125.7(5) . . ?
O12 C17 C11 117.6(5) . . ?
O11 C17 C11 116.6(5) . . ?
N11 C20 H201 109.7 . . ?
N11 C20 H202 109.7 . . ?
H201 C20 H202 109.5 . . ?
N11 C20 H203 109.0 . . ?
H201 C20 H203 109.5 . . ?
H202 C20 H203 109.5 . . ?
N11 C18 H181 114.8 . . ?
N11 C18 H182 105.7 . . ?
H181 C18 H182 109.5 . . ?
N11 C18 H183 107.8 . . ?
H181 C18 H183 109.5 . . ?
H182 C18 H183 109.5 . . ?
C19 N11 C19 0.0(5) 1 . ?
C19 N11 C18 107.9(5) 1 . ?
C19 N11 C18 107.9(5) . . ?
C19 N11 C13 109.7(4) 1 . ?
C19 N11 C13 109.7(4) . . ?
C18 N11 C13 113.5(4) . . ?
C19 N11 C20 109.5(5) 1 . ?
C19 N11 C20 109.5(5) . . ?
C18 N11 C20 105.4(5) . . ?
C13 N11 C20 110.6(4) . . ?
C19 C19 N11 0(10) 1 . ?
C19 C19 H191 0.0 1 . ?
N11 C19 H191 109.5 . . ?
C19 C19 H192 0.0 1 . ?
N11 C19 H192 109.5 . . ?
H191 C19 H192 109.5 . . ?
C19 C19 H193 0.0 1 . ?
N11 C19 H193 109.5 . . ?
H191 C19 H193 109.5 . . ?
H192 C19 H193 109.5 . . ?
C27 O21 H21 109.5 . . ?
C28 N21 C23 112.8(4) . . ?
C28 N21 C30 108.0(5) . . ?
C23 N21 C30 109.6(5) . . ?
C28 N21 C29 107.7(5) . . ?
C23 N21 C29 108.9(4) . . ?
C30 N21 C29 109.8(5) . . ?
C26 C21 C22 119.3(5) . . ?
C26 C21 C27 121.8(5) . . ?
C22 C21 C27 118.7(5) . . ?
C23 C22 C21 119.9(5) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 120.4(5) . . ?
C22 C23 N21 121.9(5) . . ?
C24 C23 N21 117.7(5) . . ?
C25 C24 C23 119.9(5) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.1(5) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 120.3(5) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
O22 C27 O21 123.7(5) . . ?
O22 C27 C21 122.9(5) . . ?
O21 C27 C21 113.3(5) . . ?
N21 C30 H301 109.4 . . ?
N21 C30 H302 115.3 . . ?
H301 C30 H302 109.5 . . ?
N21 C30 H303 103.5 . . ?
H301 C30 H303 109.5 . . ?
H302 C30 H303 109.5 . . ?
N21 C28 H281 112.4 . . ?
N21 C28 H282 106.9 . . ?
H281 C28 H282 109.5 . . ?
N21 C28 H283 109.1 . . ?
H281 C28 H283 109.5 . . ?
H282 C28 H283 109.5 . . ?
N21 C29 H291 108.0 . . ?
N21 C29 H292 107.7 . . ?
H291 C29 H292 109.5 . . ?
N21 C29 H293 112.7 . . ?
H291 C29 H293 109.5 . . ?
H292 C29 H293 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
_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 -0.7(8) . . . . ?
C7 C1 C2 C3 -176.8(5) . . . . ?
C1 C2 C3 C4 1.9(8) . . . . ?
C1 C2 C3 N1 -178.9(5) . . . . ?
C8 N1 C3 C4 -179.2(5) . . . . ?
C9 N1 C3 C4 -58.6(7) . . . . ?
C10 N1 C3 C4 60.6(7) . . . . ?
C8 N1 C3 C2 1.5(7) . . . . ?
C9 N1 C3 C2 122.2(6) . . . . ?
C10 N1 C3 C2 -118.6(6) . . . . ?
C2 C3 C4 C5 -2.2(9) . . . . ?
N1 C3 C4 C5 178.5(4) . . . . ?
C3 C4 C5 C6 1.2(7) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C2 C1 C6 C5 -0.3(6) . . . . ?
C7 C1 C6 C5 175.8(4) . . . . ?
C6 C1 C7 O2 -170.0(6) . . . . ?
C2 C1 C7 O2 6.2(9) . . . . ?
C6 C1 C7 O1 9.9(8) . . . . ?
C2 C1 C7 O1 -174.0(5) . . . . ?
C16 C11 C12 C13 0.2(8) . . . . ?
C17 C11 C12 C13 -177.4(5) . . . . ?
C11 C12 C13 C14 -0.3(9) . . . . ?
C11 C12 C13 N11 -179.2(5) . . . . ?
C12 C13 C14 C15 1.0(10) . . . . ?
N11 C13 C14 C15 180.0(6) . . . . ?
C13 C14 C15 C16 -1.5(11) . . . . ?
C12 C11 C16 C15 -0.7(9) . . . . ?
C17 C11 C16 C15 176.9(6) . . . . ?
C14 C15 C16 C11 1.4(10) . . . . ?
C16 C11 C17 O12 -171.3(5) . . . . ?
C12 C11 C17 O12 6.3(8) . . . . ?
C16 C11 C17 O11 5.6(8) . . . . ?
C12 C11 C17 O11 -176.8(5) . . . . ?
C14 C13 N11 C19 -73.8(7) . . . 1 ?
C12 C13 N11 C19 105.1(6) . . . 1 ?
C14 C13 N11 C19 -73.8(7) . . . . ?
C12 C13 N11 C19 105.1(6) . . . . ?
C14 C13 N11 C18 165.4(6) . . . . ?
C12 C13 N11 C18 -15.6(7) . . . . ?
C14 C13 N11 C20 47.2(7) . . . . ?
C12 C13 N11 C20 -133.9(6) . . . . ?
C18 N11 C19 C19 0.0(2) . . . 1 ?
C13 N11 C19 C19 0.0(2) . . . 1 ?
C20 N11 C19 C19 0.00(13) . . . 1 ?
C26 C21 C22 C23 -0.8(8) . . . . ?
C27 C21 C22 C23 -177.7(5) . . . . ?
C21 C22 C23 C24 2.6(8) . . . . ?
C21 C22 C23 N21 -178.6(5) . . . . ?
C28 N21 C23 C22 2.1(7) . . . . ?
C30 N21 C23 C22 -118.3(6) . . . . ?
C29 N21 C23 C22 121.6(6) . . . . ?
C28 N21 C23 C24 -179.0(5) . . . . ?
C30 N21 C23 C24 60.6(7) . . . . ?
C29 N21 C23 C24 -59.5(7) . . . . ?
C22 C23 C24 C25 -2.2(9) . . . . ?
N21 C23 C24 C25 178.9(5) . . . . ?
C23 C24 C25 C26 0.0(9) . . . . ?
C24 C25 C26 C21 1.7(9) . . . . ?
C22 C21 C26 C25 -1.3(9) . . . . ?
C27 C21 C26 C25 175.4(5) . . . . ?
C26 C21 C27 O22 -170.2(6) . . . . ?
C22 C21 C27 O22 6.5(10) . . . . ?
C26 C21 C27 O21 7.1(9) . . . . ?
C22 C21 C27 O21 -176.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.915
_diffrn_reflns_theta_full        27.91
_diffrn_measured_fraction_theta_full 0.915
_refine_diff_density_max         1.160
_refine_diff_density_min         -0.871
_refine_diff_density_rms         0.098
#END
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_1_1
_database_code_depnum_ccdc_archive 'CCDC 1056077'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
3-trimethylammonium-benzoic acid iodide 
;



_chemical_name_common            '3-trimethylammonium-benzoic acid iodide'
_chemical_melting_point          502

_chemical_formula_moiety         'C10 H14 N O2, I'

_chemical_formula_sum            'C10 H14 I N O2'

_chemical_formula_weight         307.12



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'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  -P2yn



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'



_cell_length_a                   8.1929(2)

_cell_length_b                   11.3278(3)

_cell_length_c                   13.1285(3)

_cell_angle_alpha                90.00

_cell_angle_beta                 105.735(3)

_cell_angle_gamma                90.00

_cell_volume                     1172.76(5)

_cell_formula_units_Z            4

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    2371

_cell_measurement_theta_min      2.41

_cell_measurement_theta_max      26.52



_exptl_crystal_description       plate

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.30

_exptl_crystal_size_mid          0.20

_exptl_crystal_size_min          0.05

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.739

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             600

_exptl_absorpt_coefficient_mu    2.708

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.527
_exptl_absorpt_correction_T_max  0.873

_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (1990)).
;



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      296(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'multiwire proportional'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            7686

_diffrn_reflns_av_R_equivalents  0.1033

_diffrn_reflns_av_sigmaI/netI    0.0698

_diffrn_reflns_limit_h_min       -10

_diffrn_reflns_limit_h_max       10

_diffrn_reflns_limit_k_min       -10

_diffrn_reflns_limit_k_max       13

_diffrn_reflns_limit_l_min       -16

_diffrn_reflns_limit_l_max       16

_diffrn_reflns_theta_min         2.41

_diffrn_reflns_theta_max         26.52

_reflns_number_total             2371

_reflns_number_gt                1940

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker FRAMBO'

_computing_cell_refinement       'Bruker FRAMBO'

_computing_data_reduction        'Bruker SHELXTL'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    
;X-Seed (Barbour, 2001) 
and POV-Ray (Persistence of Vision, 2004)

Mercury (2008)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'



_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 > 2sigma(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.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1421P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         2371

_refine_ls_number_parameters     128

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0765

_refine_ls_R_factor_gt           0.0675

_refine_ls_wR_factor_ref         0.1988

_refine_ls_wR_factor_gt          0.1846

_refine_ls_goodness_of_fit_ref   1.017

_refine_ls_restrained_S_all      1.017

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



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




























I1 I 0.36487(6) 0.92509(4) 0.69284(3) 0.0412(3) Uani 1 1 d . . .
O1 O 0.3436(7) 0.6306(5) 0.6246(5) 0.0525(13) Uani 1 1 d . . .
H1 H 0.3528 0.6961 0.6522 0.071 Uiso 1 1 calc R . .
O2 O 0.6026(9) 0.6055(7) 0.7321(7) 0.080(2) Uani 1 1 d . . .
C7 C 0.4815(10) 0.5688(7) 0.6658(6) 0.0450(18) Uani 1 1 d . . .
C1 C 0.4722(9) 0.4472(7) 0.6228(5) 0.0389(15) Uani 1 1 d . . .
C2 C 0.3230(8) 0.3970(6) 0.5630(5) 0.0326(13) Uani 1 1 d . . .
H2 H 0.2232 0.4408 0.5469 0.039 Uiso 1 1 calc R . .
C3 C 0.3210(8) 0.2815(6) 0.5270(5) 0.0318(13) Uani 1 1 d . . .
C4 C 0.4679(9) 0.2161(7) 0.5481(6) 0.0420(16) Uani 1 1 d . . .
H4 H 0.4657 0.1388 0.5238 0.050 Uiso 1 1 calc R . .
C5 C 0.6195(9) 0.2659(8) 0.6058(6) 0.0454(17) Uani 1 1 d . . .
H5 H 0.7192 0.2223 0.6196 0.054 Uiso 1 1 calc R . .
C6 C 0.6227(9) 0.3822(8) 0.6435(5) 0.0423(16) Uani 1 1 d . . .
H6 H 0.7244 0.4157 0.6820 0.051 Uiso 1 1 calc R . .
N1 N 0.1537(8) 0.2301(5) 0.4665(4) 0.0372(12) Uani 1 1 d . . .
C8 C 0.0690(11) 0.3107(8) 0.3766(7) 0.053(2) Uani 1 1 d . . .
H81 H 0.0539 0.3873 0.4041 0.080 Uiso 1 1 calc R . .
H82 H -0.0394 0.2788 0.3398 0.080 Uiso 1 1 calc R . .
H83 H 0.1386 0.3176 0.3287 0.080 Uiso 1 1 calc R . .
C9 C 0.0442(11) 0.2154(9) 0.5403(7) 0.058(2) Uani 1 1 d . . .
H91 H 0.0297 0.2904 0.5706 0.087 Uiso 1 1 calc R . .
H92 H 0.0972 0.1612 0.5956 0.087 Uiso 1 1 calc R . .
H93 H -0.0645 0.1850 0.5019 0.087 Uiso 1 1 calc R . .
C10 C 0.1729(12) 0.1109(8) 0.4197(6) 0.054(2) Uani 1 1 d . . .
H101 H 0.2414 0.1185 0.3712 0.081 Uiso 1 1 calc R . .
H102 H 0.0630 0.0811 0.3828 0.081 Uiso 1 1 calc R . .
H103 H 0.2263 0.0572 0.4753 0.081 Uiso 1 1 calc R . .






_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_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag













O1 C7 1.315(10) . ?
O2 C7 1.203(10) . ?
C7 C1 1.483(11) . ?
C1 C2 1.383(9) . ?
C1 C6 1.399(11) . ?
C2 C3 1.391(10) . ?
C3 C4 1.376(10) . ?
C3 N1 1.502(8) . ?
C4 C5 1.387(11) . ?
C5 C6 1.404(12) . ?
N1 C9 1.498(9) . ?
N1 C8 1.505(9) . ?
N1 C10 1.509(10) . ?



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



















O2 C7 O1 124.2(8) . . ?
O2 C7 C1 123.0(8) . . ?
O1 C7 C1 112.8(7) . . ?
C2 C1 C6 119.4(7) . . ?
C2 C1 C7 123.0(7) . . ?
C6 C1 C7 117.6(7) . . ?
C1 C2 C3 120.4(6) . . ?
C4 C3 C2 120.6(6) . . ?
C4 C3 N1 121.4(7) . . ?
C2 C3 N1 118.0(6) . . ?
C3 C4 C5 119.7(7) . . ?
C4 C5 C6 120.2(7) . . ?
C5 C6 C1 119.6(7) . . ?
C9 N1 C3 108.8(5) . . ?
C9 N1 C8 110.2(7) . . ?
C3 N1 C8 109.9(6) . . ?
C9 N1 C10 108.1(6) . . ?
C3 N1 C10 112.4(6) . . ?
C8 N1 C10 107.5(6) . . ?


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




















O2 C7 C1 C2 166.7(9) . . . . ?
O1 C7 C1 C2 -12.6(10) . . . . ?
O2 C7 C1 C6 -13.8(13) . . . . ?
O1 C7 C1 C6 166.8(6) . . . . ?
C6 C1 C2 C3 2.3(10) . . . . ?
C7 C1 C2 C3 -178.3(6) . . . . ?
C1 C2 C3 C4 -1.4(10) . . . . ?
C1 C2 C3 N1 177.4(6) . . . . ?
C2 C3 C4 C5 -0.1(10) . . . . ?
N1 C3 C4 C5 -178.9(6) . . . . ?
C3 C4 C5 C6 0.7(10) . . . . ?
C4 C5 C6 C1 0.2(10) . . . . ?
C2 C1 C6 C5 -1.6(10) . . . . ?
C7 C1 C6 C5 178.9(6) . . . . ?
C4 C3 N1 C9 110.8(7) . . . . ?
C2 C3 N1 C9 -68.0(8) . . . . ?
C4 C3 N1 C8 -128.5(7) . . . . ?
C2 C3 N1 C8 52.6(8) . . . . ?
C4 C3 N1 C10 -8.8(9) . . . . ?
C2 C3 N1 C10 172.3(6) . . . . ?


_diffrn_measured_fraction_theta_max 0.975

_diffrn_reflns_theta_full        26.52

_diffrn_measured_fraction_theta_full 0.975

_refine_diff_density_max         2.442

_refine_diff_density_min         -1.653

_refine_diff_density_rms         0.234

