# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1817459'
_audit_update_record             
;
2018-01-16 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '3-(iodoethynyl)benzoic acid'
_chemical_name_common            '3-iodoethynylbenzoic acid'
_chemical_melting_point          455
_chemical_formula_moiety         'C9 H5 I O2'
_chemical_formula_sum            'C9 H5 I O2'
_chemical_formula_weight         272.03

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_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                   4.7508(4)
_cell_length_b                   28.730(2)
_cell_length_c                   6.5630(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.119(5)
_cell_angle_gamma                90
_cell_volume                     895.17(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3758
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      24.33

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.018
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    3.531
_shelx_estimated_absorpt_T_min   0.438
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6419
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14806
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.418
_diffrn_reflns_theta_max         28.399
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2244
_reflns_number_gt                1751
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;


_computing_data_collection       'APEX II (Bruker, 2009)'
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'XT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0368P)²+1.0995P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2244
_refine_ls_number_parameters     113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.28562(6) 0.26575(2) 0.78104(4) 0.05119(12) Uani 1 1 d . . . . .
C1 C -0.1034(8) 0.31057(13) 0.5942(6) 0.0408(9) Uani 1 1 d . . . . .
C2 C 0.0132(8) 0.33658(12) 0.4847(6) 0.0375(8) Uani 1 1 d . . . . .
C3 C 0.1487(7) 0.36828(12) 0.3496(6) 0.0347(7) Uani 1 1 d . . . . .
C4 C 0.0698(8) 0.37089(14) 0.1440(6) 0.0423(9) Uani 1 1 d . . . . .
H4 H -0.0742 0.3510 0.0901 0.051 Uiso 1 1 calc R U . . .
C5 C 0.1982(9) 0.40215(15) 0.0169(6) 0.0468(10) Uani 1 1 d . . . . .
H5 H 0.1423 0.4034 -0.1234 0.056 Uiso 1 1 calc R U . . .
C6 C 0.4070(8) 0.43155(14) 0.0922(6) 0.0422(9) Uani 1 1 d . . . . .
H6 H 0.4945 0.4530 0.0043 0.051 Uiso 1 1 calc R U . . .
C7 C 0.4882(7) 0.42949(12) 0.2980(6) 0.0344(8) Uani 1 1 d . . . . .
C8 C 0.3615(7) 0.39794(12) 0.4263(6) 0.0342(8) Uani 1 1 d . . . . .
H8 H 0.4193 0.3965 0.5663 0.041 Uiso 1 1 calc R U . . .
C9 C 0.7091(7) 0.46078(12) 0.3863(6) 0.0353(8) Uani 1 1 d . . . . .
O1 O 0.7729(6) 0.45942(10) 0.5722(4) 0.0448(6) Uani 1 1 d . . . . .
O2 O 0.8255(7) 0.48849(11) 0.2600(5) 0.0464(7) Uani 1 1 d . . . . .
H2 H 0.938(12) 0.502(2) 0.309(9) 0.069(19) Uiso 1 1 d . . . . .


_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
I1 C1 1.998(4) . ?
C1 C2 1.188(5) . ?
C2 C3 1.439(5) . ?
C3 C4 1.389(5) . ?
C3 C8 1.402(5) . ?
C4 C5 1.383(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(5) . ?
C7 C9 1.484(5) . ?
C8 H8 0.9500 . ?
C9 O1 1.247(5) . ?
C9 O2 1.288(5) . ?
O2 H2 0.72(6) . ?

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 I1 177.9(4) . . ?
C1 C2 C3 178.7(4) . . ?
C4 C3 C8 118.8(4) . . ?
C4 C3 C2 121.5(3) . . ?
C8 C3 C2 119.8(3) . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.4(4) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 C9 118.3(3) . . ?
C6 C7 C9 121.3(3) . . ?
C7 C8 C3 120.1(3) . . ?
C7 C8 H8 119.9 . . ?
C3 C8 H8 119.9 . . ?
O1 C9 O2 123.7(4) . . ?
O1 C9 C7 120.4(3) . . ?
O2 C9 C7 115.9(3) . . ?
C9 O2 H2 111(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
C8 C3 C4 C5 0.0(6) . . . . ?
C2 C3 C4 C5 178.8(4) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
C4 C5 C6 C7 0.1(6) . . . . ?
C5 C6 C7 C8 0.4(6) . . . . ?
C5 C6 C7 C9 -179.3(4) . . . . ?
C6 C7 C8 C3 -0.7(5) . . . . ?
C9 C7 C8 C3 179.0(3) . . . . ?
C4 C3 C8 C7 0.5(5) . . . . ?
C2 C3 C8 C7 -178.3(3) . . . . ?
C8 C7 C9 O1 -1.9(5) . . . . ?
C6 C7 C9 O1 177.8(4) . . . . ?
C8 C7 C9 O2 178.1(3) . . . . ?
C6 C7 C9 O2 -2.2(5) . . . . ?

_refine_diff_density_max         1.457
_refine_diff_density_min         -0.977
_refine_diff_density_rms         0.103


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1817909'
_audit_update_record             
;
2018-01-18 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        (3-iodoethynylbenzoate)2(piperidinium)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H4 I1 O2)(C4 H12 N2)'
_chemical_formula_sum            'C11 H10 I N O2'
_chemical_formula_weight         315.10

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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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

_cell_length_a                   16.7005(8)
_cell_length_b                   8.0961(4)
_cell_length_c                   8.3096(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.243(3)
_cell_angle_gamma                90
_cell_volume                     1123.52(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5248
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      29.40
_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.863
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.811
_exptl_crystal_size_mid          0.238
_exptl_crystal_size_min          0.108
_exptl_absorpt_coefficient_mu    2.829
_shelx_estimated_absorpt_T_min   0.207
_shelx_estimated_absorpt_T_max   0.750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6070
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12635
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.439
_diffrn_reflns_theta_max         30.559
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3217
_reflns_number_gt                2453
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX II (Bruker, 2009)'
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'XT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0297P)²+1.1544P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3217
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0814
_refine_ls_wR_factor_gt          0.0729
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1076(2) 0.0902(4) 0.2362(6) 0.0358(8) Uani 1 1 d . . . . .
C2 C 0.14965(19) 0.2086(4) 0.2448(5) 0.0334(8) Uani 1 1 d . . . . .
C3 C 0.19691(18) 0.3560(4) 0.2549(5) 0.0280(7) Uani 1 1 d . . . . .
C4 C 0.1844(2) 0.4838(5) 0.1447(5) 0.0342(9) Uani 1 1 d . . . . .
H4 H 0.145755 0.470612 0.061379 0.041 Uiso 1 1 calc R U . . .
C5 C 0.2272(2) 0.6284(5) 0.1553(5) 0.0360(9) Uani 1 1 d . . . . .
H5 H 0.217768 0.714965 0.080465 0.043 Uiso 1 1 calc R U . . .
C6 C 0.28437(19) 0.6476(4) 0.2757(5) 0.0299(8) Uani 1 1 d . . . . .
H6 H 0.314145 0.747359 0.282483 0.036 Uiso 1 1 calc R U . . .
C7 C 0.29830(19) 0.5222(4) 0.3861(4) 0.0238(7) Uani 1 1 d . . . . .
C8 C 0.2542(2) 0.3773(4) 0.3758(5) 0.0257(7) Uani 1 1 d . . . . .
H8 H 0.263069 0.291605 0.451913 0.031 Uiso 1 1 calc R U . . .
C9 C 0.3597(2) 0.5430(4) 0.5192(5) 0.0253(7) Uani 1 1 d . . . . .
C10 C 0.5269(2) 0.5412(5) 0.8405(4) 0.0295(7) Uani 1 1 d . . . . .
H10A H 0.536547 0.625311 0.756229 0.035 Uiso 1 1 calc R U . . .
H10B H 0.543392 0.432411 0.797469 0.035 Uiso 1 1 calc R U . . .
C11 C 0.5764(2) 0.5818(4) 0.9880(5) 0.0291(8) Uani 1 1 d . . . . .
H11A H 0.633984 0.577771 0.960681 0.035 Uiso 1 1 calc R U . . .
H11B H 0.563693 0.695088 1.024776 0.035 Uiso 1 1 calc R U . . .
I1 I 0.03431(2) -0.10432(3) 0.23344(5) 0.04844(11) Uani 1 1 d . . . . .
N1 N 0.44044(17) 0.5374(4) 0.8808(4) 0.0266(6) Uani 1 1 d . . . . .
O1 O 0.40578(16) 0.6653(3) 0.5152(3) 0.0313(6) Uani 1 1 d . . . . .
O2 O 0.35982(17) 0.4356(3) 0.6281(3) 0.0350(6) Uani 1 1 d . . . . .
H1A H 0.418(2) 0.639(5) 0.918(5) 0.027(11) Uiso 1 1 d . . . . .
H1B H 0.413(3) 0.501(6) 0.783(7) 0.062(15) Uiso 1 1 d . . . . .


_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
C1 C2 1.190(5) . ?
C1 I1 1.995(3) . ?
C2 C3 1.433(4) . ?
C3 C8 1.395(5) . ?
C3 C4 1.397(5) . ?
C4 C5 1.375(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(4) . ?
C7 C9 1.515(5) . ?
C8 H8 0.9500 . ?
C9 O1 1.254(4) . ?
C9 O2 1.255(5) . ?
C10 N1 1.485(5) . ?
C10 C11 1.512(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N1 1.484(5) 3_667 ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N1 H1A 0.96(4) . ?
N1 H1B 0.98(6) . ?

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 I1 176.8(4) . . ?
C1 C2 C3 177.3(4) . . ?
C8 C3 C4 118.8(3) . . ?
C8 C3 C2 121.4(3) . . ?
C4 C3 C2 119.8(3) . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.9(4) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 119.4(3) . . ?
C6 C7 C9 120.8(3) . . ?
C8 C7 C9 119.8(3) . . ?
C7 C8 C3 120.7(3) . . ?
C7 C8 H8 119.6 . . ?
C3 C8 H8 119.6 . . ?
O1 C9 O2 124.6(3) . . ?
O1 C9 C7 118.8(3) . . ?
O2 C9 C7 116.6(3) . . ?
N1 C10 C11 110.5(3) . . ?
N1 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N1 C11 C10 110.5(3) 3_667 . ?
N1 C11 H11A 109.5 3_667 . ?
C10 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 3_667 . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 N1 C10 111.5(3) 3_667 . ?
C11 N1 H1A 104(2) 3_667 . ?
C10 N1 H1A 116(2) . . ?
C11 N1 H1B 109(3) 3_667 . ?
C10 N1 H1B 106(3) . . ?
H1A N1 H1B 110(4) . . ?

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
C8 C3 C4 C5 -0.4(6) . . . . ?
C2 C3 C4 C5 177.9(4) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C4 C5 C6 C7 -0.4(6) . . . . ?
C5 C6 C7 C8 -0.4(6) . . . . ?
C5 C6 C7 C9 -179.1(4) . . . . ?
C6 C7 C8 C3 0.8(5) . . . . ?
C9 C7 C8 C3 179.5(3) . . . . ?
C4 C3 C8 C7 -0.4(6) . . . . ?
C2 C3 C8 C7 -178.6(4) . . . . ?
C6 C7 C9 O1 -9.9(5) . . . . ?
C8 C7 C9 O1 171.3(3) . . . . ?
C6 C7 C9 O2 169.1(3) . . . . ?
C8 C7 C9 O2 -9.6(5) . . . . ?
N1 C10 C11 N1 56.1(4) . . . 3_667 ?
C11 C10 N1 C11 -56.7(4) . . . 3_667 ?

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
C11 H11B O2 0.99 2.66 3.207(5) 115.3 2_656
N1 H1A O1 0.96(4) 1.79(4) 2.717(4) 163(4) 4_576
N1 H1B O2 0.98(6) 1.65(6) 2.622(4) 175(5) .
N1 H1B O1 0.98(6) 2.60(5) 3.259(4) 125(4) .
C11 H11B O2 0.99 2.66 3.207(5) 115.3 2_656
N1 H1A O1 0.96(4) 1.79(4) 2.717(4) 163(4) 4_576
N1 H1B O1 0.98(6) 2.60(5) 3.259(4) 125(4) .
N1 H1B O2 0.98(6) 1.65(6) 2.622(4) 175(5) .

_refine_diff_density_max         0.731
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.090


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1817907'
_audit_update_record             
;
2018-01-18 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'(3-iodoethynylbenzoic acid)(1,4-diazabicyclo[2.2.2]octane)'
_chemical_name_common            '(3-iodoethynylbenzoic acid)(DABCO)'
_chemical_melting_point          445
_chemical_formula_moiety         'C9 H5 I1 O2, C6 H12 N2'
_chemical_formula_sum            'C15 H17 I N2 O2'
_chemical_formula_weight         384.20

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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

_cell_length_a                   17.5218(8)
_cell_length_b                   6.5563(3)
_cell_length_c                   27.7452(12)
_cell_angle_alpha                90
_cell_angle_beta                 107.586(3)
_cell_angle_gamma                90
_cell_volume                     3038.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3441
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      20.85
_exptl_crystal_description       Needles
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.044
_exptl_absorpt_coefficient_mu    2.111
_shelx_estimated_absorpt_T_min   0.530
_shelx_estimated_absorpt_T_max   0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6521
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20095
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_av_R_equivalents  0.1022
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.439
_diffrn_reflns_theta_max         25.244
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2744
_reflns_number_gt                1709
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX II (Bruker, 2009)'
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'XT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0598P)²+3.3927P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2744
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1265
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.10805(3) 0.19306(8) 0.54667(2) 0.0490(2) Uani 1 1 d . . . . .
O1 O 0.1264(4) 0.7515(8) 0.2534(2) 0.0578(15) Uani 1 1 d . . . . .
O2 O 0.1064(3) 0.4462(8) 0.28201(19) 0.0598(15) Uani 1 1 d . . . . .
C5 C 0.1822(4) 0.9806(11) 0.4026(3) 0.0426(18) Uani 1 1 d . . . . .
H5 H 0.199708 1.117011 0.410729 0.051 Uiso 1 1 calc R U . . .
C8 C 0.1310(4) 0.5878(11) 0.3785(2) 0.0357(16) Uani 1 1 d . . . . .
H8 H 0.113875 0.451234 0.370201 0.043 Uiso 1 1 calc R U . . .
C4 C 0.1745(4) 0.8524(11) 0.4402(3) 0.045(2) Uani 1 1 d . . . . .
H4 H 0.187742 0.899433 0.474079 0.054 Uiso 1 1 calc R U . . .
C1 C 0.1242(5) 0.3939(13) 0.4955(3) 0.051(2) Uani 1 1 d . . . . .
C6 C 0.1648(4) 0.9135(11) 0.3533(3) 0.0370(16) Uani 1 1 d . . . . .
H6 H 0.170352 1.003446 0.327740 0.044 Uiso 1 1 calc R U . . .
C3 C 0.1474(4) 0.6540(11) 0.4284(3) 0.0427(19) Uani 1 1 d . . . . .
C2 C 0.1356(4) 0.5152(13) 0.4662(3) 0.047(2) Uani 1 1 d . . . . .
C7 C 0.1391(4) 0.7149(11) 0.3411(3) 0.0351(16) Uani 1 1 d . . . . .
C9 C 0.1223(4) 0.6363(12) 0.2879(3) 0.0433(19) Uani 1 1 d . . . . .
N1 N 0.4018(3) 0.5671(9) 0.3781(2) 0.0378(14) Uani 1 1 d . . . . .
N2 N 0.4013(3) 0.7850(9) 0.3025(2) 0.0382(14) Uani 1 1 d . . . . .
C15 C 0.3251(4) 0.6686(12) 0.2915(3) 0.048(2) Uani 1 1 d . . . . .
H15A H 0.316479 0.588278 0.260040 0.058 Uiso 1 1 calc R U . . .
H15B H 0.279509 0.763735 0.286667 0.058 Uiso 1 1 calc R U . . .
C14 C 0.3303(4) 0.5260(12) 0.3360(3) 0.0464(19) Uani 1 1 d . . . . .
H14A H 0.282189 0.544267 0.347235 0.056 Uiso 1 1 calc R U . . .
H14B H 0.331280 0.382699 0.324938 0.056 Uiso 1 1 calc R U . . .
C12 C 0.4722(4) 0.5225(13) 0.3620(3) 0.053(2) Uani 1 1 d . . . . .
H12A H 0.474887 0.373982 0.356269 0.064 Uiso 1 1 calc R U . . .
H12B H 0.521131 0.562362 0.389087 0.064 Uiso 1 1 calc R U . . .
C11 C 0.4099(5) 0.9166(12) 0.3470(3) 0.051(2) Uani 1 1 d . . . . .
H11A H 0.367614 1.022525 0.338956 0.061 Uiso 1 1 calc R U . . .
H11B H 0.462639 0.985306 0.356626 0.061 Uiso 1 1 calc R U . . .
C13 C 0.4693(4) 0.6357(11) 0.3138(3) 0.0426(19) Uani 1 1 d . . . . .
H13A H 0.520382 0.708674 0.318112 0.051 Uiso 1 1 calc R U . . .
H13B H 0.461217 0.538114 0.285480 0.051 Uiso 1 1 calc R U . . .
C10 C 0.4024(5) 0.7827(13) 0.3905(3) 0.058(2) Uani 1 1 d . . . . .
H10A H 0.447803 0.810986 0.421051 0.069 Uiso 1 1 calc R U . . .
H10B H 0.352281 0.817346 0.398119 0.069 Uiso 1 1 calc R U . . .
H2A H 0.401(5) 0.863(14) 0.270(4) 0.09(3) Uiso 1 1 d . . . . .


_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
I1 C1 2.018(9) . ?
O1 C9 1.237(9) . ?
O2 C9 1.277(9) . ?
C5 C4 1.377(10) . ?
C5 C6 1.381(9) . ?
C5 H5 0.9500 . ?
C8 C7 1.371(9) . ?
C8 C3 1.396(9) . ?
C8 H8 0.9500 . ?
C4 C3 1.389(10) . ?
C4 H4 0.9500 . ?
C1 C2 1.196(10) . ?
C6 C7 1.385(10) . ?
C6 H6 0.9500 . ?
C3 C2 1.451(11) . ?
C7 C9 1.507(10) . ?
N1 C10 1.454(10) . ?
N1 C14 1.458(8) . ?
N1 C12 1.463(8) . ?
N2 C11 1.476(9) . ?
N2 C15 1.488(9) . ?
N2 C13 1.499(9) . ?
N2 H2A 1.04(10) . ?
C15 C14 1.530(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C12 C13 1.516(10) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C11 C10 1.530(11) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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
C4 C5 C6 120.8(7) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C8 C3 121.6(7) . . ?
C7 C8 H8 119.2 . . ?
C3 C8 H8 119.2 . . ?
C5 C4 C3 119.9(7) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C2 C1 I1 178.1(7) . . ?
C5 C6 C7 120.0(7) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C4 C3 C8 118.6(7) . . ?
C4 C3 C2 122.0(6) . . ?
C8 C3 C2 119.4(7) . . ?
C1 C2 C3 176.6(8) . . ?
C8 C7 C6 119.1(6) . . ?
C8 C7 C9 120.0(7) . . ?
C6 C7 C9 120.9(6) . . ?
O1 C9 O2 124.0(7) . . ?
O1 C9 C7 120.6(7) . . ?
O2 C9 C7 115.4(7) . . ?
C10 N1 C14 108.1(6) . . ?
C10 N1 C12 108.7(6) . . ?
C14 N1 C12 108.5(6) . . ?
C11 N2 C15 109.2(6) . . ?
C11 N2 C13 109.5(5) . . ?
C15 N2 C13 108.4(6) . . ?
C11 N2 H2A 115(5) . . ?
C15 N2 H2A 108(5) . . ?
C13 N2 H2A 107(5) . . ?
N2 C15 C14 108.5(6) . . ?
N2 C15 H15A 110.0 . . ?
C14 C15 H15A 110.0 . . ?
N2 C15 H15B 110.0 . . ?
C14 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
N1 C14 C15 111.2(6) . . ?
N1 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
N1 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N1 C12 C13 111.4(6) . . ?
N1 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
N1 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N2 C11 C10 108.2(6) . . ?
N2 C11 H11A 110.1 . . ?
C10 C11 H11A 110.1 . . ?
N2 C11 H11B 110.1 . . ?
C10 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
N2 C13 C12 108.5(6) . . ?
N2 C13 H13A 110.0 . . ?
C12 C13 H13A 110.0 . . ?
N2 C13 H13B 110.0 . . ?
C12 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
N1 C10 C11 111.6(6) . . ?
N1 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
N1 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?

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 C5 C4 C3 -1.3(10) . . . . ?
C4 C5 C6 C7 0.1(10) . . . . ?
C5 C4 C3 C8 2.1(10) . . . . ?
C5 C4 C3 C2 -177.8(7) . . . . ?
C7 C8 C3 C4 -1.7(10) . . . . ?
C7 C8 C3 C2 178.1(6) . . . . ?
C3 C8 C7 C6 0.5(10) . . . . ?
C3 C8 C7 C9 178.8(6) . . . . ?
C5 C6 C7 C8 0.3(10) . . . . ?
C5 C6 C7 C9 -178.0(6) . . . . ?
C8 C7 C9 O1 177.2(7) . . . . ?
C6 C7 C9 O1 -4.6(10) . . . . ?
C8 C7 C9 O2 -4.6(10) . . . . ?
C6 C7 C9 O2 173.7(6) . . . . ?
C11 N2 C15 C14 -64.3(7) . . . . ?
C13 N2 C15 C14 54.9(7) . . . . ?
C10 N1 C14 C15 53.9(8) . . . . ?
C12 N1 C14 C15 -63.8(8) . . . . ?
N2 C15 C14 N1 8.2(8) . . . . ?
C10 N1 C12 C13 -63.8(8) . . . . ?
C14 N1 C12 C13 53.6(8) . . . . ?
C15 N2 C11 C10 54.5(8) . . . . ?
C13 N2 C11 C10 -64.0(8) . . . . ?
C11 N2 C13 C12 54.1(8) . . . . ?
C15 N2 C13 C12 -65.0(7) . . . . ?
N1 C12 C13 N2 9.2(9) . . . . ?
C14 N1 C10 C11 -64.3(8) . . . . ?
C12 N1 C10 C11 53.3(8) . . . . ?
N2 C11 C10 N1 8.9(9) . . . . ?

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
C15 H15A O1 0.99 2.50 3.223(9) 129.8 4_545
C15 H15B O1 0.99 2.56 3.363(9) 138.0 .
C14 H14B O1 0.99 2.64 3.332(9) 126.8 4_545
C13 H13A O2 0.99 2.57 3.460(9) 149.4 3
C13 H13B O1 0.99 2.46 3.277(9) 139.7 4_545
C15 H15A O1 0.99 2.50 3.223(9) 129.8 4_545
C15 H15B O1 0.99 2.56 3.363(9) 138.0 .
C14 H14B O1 0.99 2.64 3.332(9) 126.8 4_545
C13 H13A O2 0.99 2.57 3.460(9) 149.4 3
C13 H13B O1 0.99 2.46 3.277(9) 139.7 4_545
N2 H2A O1 1.04(10) 2.64(9) 3.397(8) 130(7) 4
N2 H2A O2 1.04(10) 1.50(10) 2.538(8) 171(8) 4

_refine_diff_density_max         1.414
_refine_diff_density_min         -1.075
_refine_diff_density_rms         0.123


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1817906'
_audit_update_record             
;
2018-01-18 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
(3-(iodoethynylpyridine)(2,3,5,6-tetramethylpyrazine)
_chemical_name_common            ?
_chemical_melting_point          427
_chemical_formula_moiety         '2(C6 H5 I1 O2), C8 H12 N2'
_chemical_formula_sum            'C26 H22 I2 N2 O4'
_chemical_formula_weight         680.25

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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7194(6)
_cell_length_b                   9.1772(10)
_cell_length_c                   19.1992(15)
_cell_angle_alpha                83.6240(10)
_cell_angle_beta                 88.7390(10)
_cell_angle_gamma                70.9770(10)
_cell_volume                     1277.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3758
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      25.28
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_F_000             660
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.138
_exptl_absorpt_coefficient_mu    2.495
_shelx_estimated_absorpt_T_min   0.590
_shelx_estimated_absorpt_T_max   0.725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6485
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15338
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.135
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5789
_reflns_number_gt                4444
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;


_computing_data_collection       'APEX II (Bruker, 2009)'
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'XT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0254P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5789
_refine_ls_number_parameters     323
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0639
_refine_ls_wR_factor_gt          0.0584
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.003
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2487(5) 0.2355(4) 0.76508(18) 0.0320(8) Uani 1 1 d . . . . .
C2 C 0.2348(5) 0.1473(4) 0.72582(18) 0.0318(8) Uani 1 1 d . . . . .
C3 C 0.2160(5) 0.0477(4) 0.67606(17) 0.0268(7) Uani 1 1 d . . . . .
C4 C 0.0491(5) 0.0204(4) 0.66794(18) 0.0333(8) Uani 1 1 d . . . . .
H4 H -0.051114 0.065700 0.696878 0.040 Uiso 1 1 calc R U . . .
C5 C 0.0290(5) -0.0707(4) 0.61871(19) 0.0374(9) Uani 1 1 d . . . . .
H5 H -0.084850 -0.088011 0.614004 0.045 Uiso 1 1 calc R U . . .
C6 C 0.1726(5) -0.1376(4) 0.57596(18) 0.0345(8) Uani 1 1 d . . . . .
H6 H 0.157659 -0.200703 0.542046 0.041 Uiso 1 1 calc R U . . .
C7 C 0.3393(4) -0.1122(4) 0.58279(16) 0.0252(7) Uani 1 1 d . . . . .
C8 C 0.3605(4) -0.0205(4) 0.63305(16) 0.0272(7) Uani 1 1 d . . . . .
H8 H 0.474840 -0.004311 0.637978 0.033 Uiso 1 1 calc R U . . .
C9 C 0.4972(4) -0.1837(4) 0.53797(17) 0.0268(7) Uani 1 1 d . . . . .
C10 C 0.2263(5) 0.1720(4) 0.21348(18) 0.0333(8) Uani 1 1 d . . . . .
C11 C 0.2206(5) 0.2673(4) 0.25190(18) 0.0311(8) Uani 1 1 d . . . . .
C12 C 0.2194(5) 0.3789(4) 0.29968(17) 0.0265(7) Uani 1 1 d . . . . .
C13 C 0.3759(5) 0.4227(4) 0.30530(18) 0.0333(8) Uani 1 1 d . . . . .
H13 H 0.480047 0.379494 0.277785 0.040 Uiso 1 1 calc R U . . .
C14 C 0.3792(5) 0.5280(4) 0.35052(18) 0.0371(9) Uani 1 1 d . . . . .
H14 H 0.485652 0.557287 0.353969 0.044 Uiso 1 1 calc R U . . .
C15 C 0.2293(5) 0.5915(4) 0.39083(17) 0.0322(8) Uani 1 1 d . . . . .
H15 H 0.233087 0.663258 0.422351 0.039 Uiso 1 1 calc R U . . .
C16 C 0.0726(4) 0.5502(4) 0.38525(16) 0.0250(7) Uani 1 1 d . . . . .
C17 C 0.0667(4) 0.4449(4) 0.33952(16) 0.0253(7) Uani 1 1 d . . . . .
H17 H -0.041180 0.417860 0.335406 0.030 Uiso 1 1 calc R U . . .
C18 C -0.0890(4) 0.6195(4) 0.42890(17) 0.0262(7) Uani 1 1 d . . . . .
C19 C 0.2895(5) 0.7919(4) 0.84194(17) 0.0353(9) Uani 1 1 d . . . . .
H19A H 0.416839 0.786573 0.833002 0.053 Uiso 1 1 calc R U . . .
H19B H 0.208045 0.897768 0.828230 0.053 Uiso 1 1 calc R U . . .
H19C H 0.257872 0.719947 0.814581 0.053 Uiso 1 1 calc R U . . .
C20 C 0.2679(4) 0.7485(4) 0.91834(17) 0.0258(7) Uani 1 1 d . . . . .
C21 C 0.2538(4) 0.8503(4) 0.96852(17) 0.0257(7) Uani 1 1 d . . . . .
C22 C 0.2496(5) 1.0145(4) 0.94817(19) 0.0401(9) Uani 1 1 d . . . . .
H22A H 0.217047 1.073008 0.988929 0.060 Uiso 1 1 calc R U . . .
H22B H 0.158372 1.063036 0.910627 0.060 Uiso 1 1 calc R U . . .
H22C H 0.370677 1.014512 0.931687 0.060 Uiso 1 1 calc R U . . .
C23 C 0.2499(5) 0.3972(4) 1.02679(19) 0.0413(9) Uani 1 1 d . . . . .
H23A H 0.282986 0.337603 0.986394 0.062 Uiso 1 1 calc R U . . .
H23B H 0.126565 0.401242 1.042005 0.062 Uiso 1 1 calc R U . . .
H23C H 0.337864 0.347154 1.065248 0.062 Uiso 1 1 calc R U . . .
C24 C 0.2535(4) 0.5586(4) 1.00652(18) 0.0272(7) Uani 1 1 d . . . . .
C25 C 0.2443(4) 0.6598(4) 1.05660(17) 0.0271(7) Uani 1 1 d . . . . .
C26 C 0.2367(5) 0.6138(4) 1.13334(18) 0.0392(9) Uani 1 1 d . . . . .
H26A H 0.356386 0.541764 1.149965 0.059 Uiso 1 1 calc R U . . .
H26B H 0.143253 0.563258 1.142143 0.059 Uiso 1 1 calc R U . . .
H26C H 0.205598 0.706335 1.158309 0.059 Uiso 1 1 calc R U . . .
I1 I 0.26466(3) 0.38730(3) 0.83031(2) 0.03272(7) Uani 1 1 d . . . . .
I2 I 0.23875(3) 0.01814(3) 0.14535(2) 0.03270(7) Uani 1 1 d . . . . .
N1 N 0.2667(4) 0.6026(3) 0.93820(14) 0.0290(6) Uani 1 1 d . . . . .
N2 N 0.2437(3) 0.8057(3) 1.03686(14) 0.0275(6) Uani 1 1 d . . . . .
O1 O 0.6446(3) -0.1556(3) 0.54654(12) 0.0335(6) Uani 1 1 d D . . . .
H1A H 0.738(6) -0.215(7) 0.532(4) 0.050 Uiso 0.5 1 d D U P A 1
O2 O 0.4748(3) -0.2680(3) 0.49332(14) 0.0433(7) Uani 1 1 d D . . . .
H2A H 0.568(7) -0.325(8) 0.478(4) 0.065 Uiso 0.5 1 d D U P B 1
O3 O -0.2358(3) 0.5900(3) 0.41960(13) 0.0371(6) Uani 1 1 d D . . . .
H3A H -0.317(8) 0.647(8) 0.440(4) 0.056 Uiso 0.5 1 d D U P C 2
O4 O -0.0712(3) 0.7043(3) 0.47396(12) 0.0334(6) Uani 1 1 d D . . . .
H4A H -0.168(6) 0.751(8) 0.490(4) 0.050 Uiso 0.5 1 d D U P D 2


_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
C1 C2 1.196(5) . ?
C1 I1 2.008(3) . ?
C2 C3 1.434(5) . ?
C3 C8 1.391(4) . ?
C3 C4 1.405(4) . ?
C4 C5 1.373(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(4) . ?
C7 C9 1.488(4) . ?
C8 H8 0.9500 . ?
C9 O1 1.264(4) . ?
C9 O2 1.267(4) . ?
C10 C11 1.194(4) . ?
C10 I2 2.008(3) . ?
C11 C12 1.447(5) . ?
C12 C17 1.393(4) . ?
C12 C13 1.402(5) . ?
C13 C14 1.376(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(4) . ?
C16 C18 1.489(4) . ?
C17 H17 0.9500 . ?
C18 O4 1.264(4) . ?
C18 O3 1.268(4) . ?
C19 C20 1.497(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 N1 1.354(4) . ?
C20 C21 1.394(4) . ?
C21 N2 1.339(4) . ?
C21 C22 1.504(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.498(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 N1 1.341(4) . ?
C24 C25 1.394(4) . ?
C25 N2 1.349(4) . ?
C25 C26 1.492(4) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
O1 H1A 0.81(2) . ?
O2 H2A 0.81(2) . ?
O3 H3A 0.81(2) . ?
O4 H4A 0.81(2) . ?

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 I1 178.4(3) . . ?
C1 C2 C3 177.2(4) . . ?
C8 C3 C4 118.3(3) . . ?
C8 C3 C2 120.9(3) . . ?
C4 C3 C2 120.7(3) . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C8 119.8(3) . . ?
C6 C7 C9 121.0(3) . . ?
C8 C7 C9 119.2(3) . . ?
C3 C8 C7 120.8(3) . . ?
C3 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
O1 C9 O2 124.2(3) . . ?
O1 C9 C7 117.9(3) . . ?
O2 C9 C7 117.9(3) . . ?
C11 C10 I2 177.4(3) . . ?
C10 C11 C12 178.0(4) . . ?
C17 C12 C13 119.3(3) . . ?
C17 C12 C11 121.8(3) . . ?
C13 C12 C11 118.9(3) . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 C18 120.2(3) . . ?
C15 C16 C18 119.5(3) . . ?
C16 C17 C12 119.8(3) . . ?
C16 C17 H17 120.1 . . ?
C12 C17 H17 120.1 . . ?
O4 C18 O3 123.5(3) . . ?
O4 C18 C16 117.6(3) . . ?
O3 C18 C16 118.9(3) . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 C21 120.0(3) . . ?
N1 C20 C19 117.4(3) . . ?
C21 C20 C19 122.6(3) . . ?
N2 C21 C20 121.3(3) . . ?
N2 C21 C22 117.3(3) . . ?
C20 C21 C22 121.4(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 C24 C25 120.9(3) . . ?
N1 C24 C23 117.6(3) . . ?
C25 C24 C23 121.5(3) . . ?
N2 C25 C24 120.4(3) . . ?
N2 C25 C26 116.9(3) . . ?
C24 C25 C26 122.7(3) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 N1 C20 118.8(3) . . ?
C21 N2 C25 118.6(3) . . ?
C9 O1 H1A 117(6) . . ?
C9 O2 H2A 116(6) . . ?
C18 O3 H3A 109(6) . . ?
C18 O4 H4A 112(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
C8 C3 C4 C5 -0.2(5) . . . . ?
C2 C3 C4 C5 177.8(3) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C4 C5 C6 C7 -0.1(6) . . . . ?
C5 C6 C7 C8 0.5(5) . . . . ?
C5 C6 C7 C9 179.5(3) . . . . ?
C4 C3 C8 C7 0.6(5) . . . . ?
C2 C3 C8 C7 -177.4(3) . . . . ?
C6 C7 C8 C3 -0.7(5) . . . . ?
C9 C7 C8 C3 -179.7(3) . . . . ?
C6 C7 C9 O1 179.7(3) . . . . ?
C8 C7 C9 O1 -1.3(5) . . . . ?
C6 C7 C9 O2 0.2(5) . . . . ?
C8 C7 C9 O2 179.2(3) . . . . ?
C17 C12 C13 C14 1.0(5) . . . . ?
C11 C12 C13 C14 -179.7(3) . . . . ?
C12 C13 C14 C15 0.1(6) . . . . ?
C13 C14 C15 C16 -0.7(6) . . . . ?
C14 C15 C16 C17 0.3(5) . . . . ?
C14 C15 C16 C18 -179.9(3) . . . . ?
C15 C16 C17 C12 0.8(5) . . . . ?
C18 C16 C17 C12 -179.0(3) . . . . ?
C13 C12 C17 C16 -1.4(5) . . . . ?
C11 C12 C17 C16 179.3(3) . . . . ?
C17 C16 C18 O4 174.1(3) . . . . ?
C15 C16 C18 O4 -5.7(5) . . . . ?
C17 C16 C18 O3 -5.4(5) . . . . ?
C15 C16 C18 O3 174.8(3) . . . . ?
N1 C20 C21 N2 1.8(5) . . . . ?
C19 C20 C21 N2 -176.7(3) . . . . ?
N1 C20 C21 C22 -178.3(3) . . . . ?
C19 C20 C21 C22 3.2(5) . . . . ?
N1 C24 C25 N2 1.8(5) . . . . ?
C23 C24 C25 N2 -178.5(3) . . . . ?
N1 C24 C25 C26 -177.6(3) . . . . ?
C23 C24 C25 C26 2.1(5) . . . . ?
C25 C24 N1 C20 -1.1(5) . . . . ?
C23 C24 N1 C20 179.2(3) . . . . ?
C21 C20 N1 C24 -0.6(5) . . . . ?
C19 C20 N1 C24 177.9(3) . . . . ?
C20 C21 N2 C25 -1.1(5) . . . . ?
C22 C21 N2 C25 179.0(3) . . . . ?
C24 C25 N2 C21 -0.6(5) . . . . ?
C26 C25 N2 C21 178.8(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
C19 H19B I2 0.98 3.32 3.892(4) 119.1 2_566
C19 H19C I1 0.98 3.02 3.812(3) 139.0 .
C22 H22A I2 0.98 2.99 3.788(4) 139.6 1_566
C22 H22C I2 0.98 3.27 4.236(4) 169.9 2_666
C23 H23A I1 0.98 2.98 3.782(4) 139.8 .
C26 H26A I1 0.98 3.24 3.923(4) 128.7 2_667
C26 H26B I1 0.98 3.07 3.921(4) 145.5 2_567
C26 H26C I2 0.98 2.94 3.748(4) 140.7 1_566
O1 H1A O4 0.81(2) 1.84(3) 2.614(3) 160(8) 1_645
O2 H2A O3 0.81(2) 1.87(3) 2.658(3) 163(9) 1_645
O3 H3A O2 0.81(2) 1.87(3) 2.658(3) 165(8) 1_465
O4 H4A O1 0.81(2) 1.82(3) 2.614(3) 166(8) 1_465

_refine_diff_density_max         0.485
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.093


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1817910'
_audit_update_record             
;
2018-01-18 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(3-iodoethynylbenzoic acid)(hexamethylenetetramine)'
_chemical_name_common            '(3-iodoethynylbenzoic acid)(urotropin)'
_chemical_melting_point          459
_chemical_formula_moiety         'C9 H5 I1 O2, C6 H12 N4'
_chemical_formula_sum            'C15 H17 I N4 O2'
_chemical_formula_weight         412.23

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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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

_cell_length_a                   14.465(5)
_cell_length_b                   16.493(5)
_cell_length_c                   6.958(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.304(4)
_cell_angle_gamma                90
_cell_volume                     1627.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1993
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      17.66
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.154
_exptl_absorpt_coefficient_mu    1.980
_shelx_estimated_absorpt_T_min   0.631
_shelx_estimated_absorpt_T_max   0.750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.599917
_exptl_absorpt_correction_T_max  0.745684
_exptl_absorpt_process_details   'TWINABS v.2012/1 (Bruker,2012)'
_exptl_absorpt_special_details   
;
    15845 data (   3716 unique ) involve domain  1 only,  mean I/sigma   2.2
    15717 data (   3685 unique ) involve domain  2 only,  mean I/sigma   1.3
     3740 data (   1362 unique ) involve   2 domains,  mean I/sigma   1.8
;
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28340
_diffrn_reflns_av_unetI/netI     0.2066
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.436
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             28340
_reflns_number_gt                13424
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX II (Bruker, 2009)'
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'XT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         28340
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1813
_refine_ls_R_factor_gt           0.0845
_refine_ls_wR_factor_ref         0.2343
_refine_ls_wR_factor_gt          0.1783
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0503(11) 0.3841(11) 0.584(2) 0.052(5) Uani 1 1 d . . . . .
C2 C 0.1114(12) 0.3772(10) 0.492(2) 0.047(5) Uani 1 1 d . . . . .
C3 C 0.1884(12) 0.3651(9) 0.391(2) 0.040(4) Uani 1 1 d . . . . .
C4 C 0.1718(12) 0.3374(10) 0.200(2) 0.050(5) Uani 1 1 d . . . . .
H4 H 0.1089 0.3287 0.1318 0.061 Uiso 1 1 calc R U . . .
C5 C 0.2459(13) 0.3223(10) 0.108(2) 0.051(5) Uani 1 1 d . . . . .
H5 H 0.2338 0.3043 -0.0239 0.062 Uiso 1 1 calc R U . . .
C6 C 0.3377(12) 0.3330(9) 0.206(2) 0.047(4) Uani 1 1 d . . . . .
H6 H 0.3886 0.3211 0.1427 0.056 Uiso 1 1 calc R U . . .
C7 C 0.3554(12) 0.3615(9) 0.399(2) 0.038(4) Uani 1 1 d . . . . .
C8 C 0.2804(11) 0.3779(9) 0.489(2) 0.040(4) Uani 1 1 d . . . . .
H8 H 0.2920 0.3981 0.6194 0.047 Uiso 1 1 calc R U . . .
C9 C 0.4541(12) 0.3711(10) 0.505(3) 0.046(5) Uani 1 1 d . . . . .
C10 C 0.7107(11) 0.3985(12) -0.191(2) 0.061(5) Uani 1 1 d . . . . .
H10A H 0.7077 0.4475 -0.2741 0.073 Uiso 1 1 calc R U . . .
H10B H 0.7075 0.3504 -0.2767 0.073 Uiso 1 1 calc R U . . .
C11 C 0.6366(12) 0.3239(10) 0.029(3) 0.052(5) Uani 1 1 d . . . . .
H11A H 0.5826 0.3216 0.0967 0.063 Uiso 1 1 calc R U . . .
H11B H 0.6334 0.2756 -0.0571 0.063 Uiso 1 1 calc R U . . .
C12 C 0.8022(11) 0.3255(11) 0.071(3) 0.056(5) Uani 1 1 d . . . . .
H12A H 0.8007 0.2771 -0.0134 0.067 Uiso 1 1 calc R U . . .
H12B H 0.8618 0.3242 0.1694 0.067 Uiso 1 1 calc R U . . .
C13 C 0.6369(13) 0.4687(10) 0.037(3) 0.064(6) Uani 1 1 d . . . . .
H13A H 0.6331 0.5187 -0.0426 0.077 Uiso 1 1 calc R U . . .
H13B H 0.5832 0.4687 0.1061 0.077 Uiso 1 1 calc R U . . .
C14 C 0.7275(14) 0.395(2) 0.290(3) 0.100(9) Uani 1 1 d . . . . .
H14A H 0.6743 0.3949 0.3604 0.120 Uiso 1 1 calc R U . . .
H14B H 0.7867 0.3948 0.3897 0.120 Uiso 1 1 calc R U . . .
C15 C 0.8036(12) 0.4681(11) 0.078(3) 0.067(6) Uani 1 1 d . . . . .
H15A H 0.8024 0.5181 -0.0008 0.081 Uiso 1 1 calc R U . . .
H15B H 0.8631 0.4676 0.1768 0.081 Uiso 1 1 calc R U . . .
I1 I -0.05129(7) 0.39352(7) 0.74554(16) 0.0525(5) Uani 1 1 d . . . . .
N1 N 0.6296(8) 0.3981(9) -0.0922(18) 0.042(3) Uani 1 1 d . . . . .
N2 N 0.7233(11) 0.3223(10) 0.171(3) 0.066(5) Uani 1 1 d . . . . .
N3 N 0.8006(8) 0.3979(9) -0.0482(18) 0.039(3) Uani 1 1 d . . . . .
N4 N 0.7237(11) 0.4684(11) 0.178(3) 0.076(5) Uani 1 1 d . . . . .
O1 O 0.4613(9) 0.3940(9) 0.6853(19) 0.076(4) Uani 1 1 d . . . . .
O2 O 0.5218(8) 0.3589(8) 0.4324(17) 0.070(4) Uani 1 1 d . . . . .
H1A H 0.524(15) 0.395(12) 0.75(3) 0.12(8) Uiso 1 1 d . . . . .


_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
C1 C2 1.19(2) . ?
C1 I1 2.025(17) . ?
C2 C3 1.44(2) . ?
C3 C4 1.38(2) . ?
C3 C8 1.39(2) . ?
C4 C5 1.37(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.38(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.40(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.38(2) . ?
C7 C9 1.48(2) . ?
C8 H8 0.9500 . ?
C9 O2 1.203(17) . ?
C9 O1 1.296(19) . ?
C10 N1 1.469(18) . ?
C10 N3 1.473(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N2 1.440(19) . ?
C11 N1 1.477(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N2 1.45(2) . ?
C12 N3 1.452(18) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N4 1.44(2) . ?
C13 N1 1.462(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N4 1.43(3) . ?
C14 N2 1.46(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 N3 1.449(19) . ?
C15 N4 1.46(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
O1 H1A 0.9(2) . ?

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 I1 178.2(16) . . ?
C1 C2 C3 176.3(19) . . ?
C4 C3 C8 119.5(16) . . ?
C4 C3 C2 120.7(16) . . ?
C8 C3 C2 119.7(16) . . ?
C5 C4 C3 120.1(16) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.8(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 119.6(16) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 119.3(16) . . ?
C8 C7 C9 121.3(16) . . ?
C6 C7 C9 119.4(16) . . ?
C7 C8 C3 120.7(16) . . ?
C7 C8 H8 119.7 . . ?
C3 C8 H8 119.7 . . ?
O2 C9 O1 122.5(16) . . ?
O2 C9 C7 123.9(17) . . ?
O1 C9 C7 113.6(15) . . ?
N1 C10 N3 111.4(13) . . ?
N1 C10 H10A 109.3 . . ?
N3 C10 H10A 109.3 . . ?
N1 C10 H10B 109.3 . . ?
N3 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
N2 C11 N1 111.1(13) . . ?
N2 C11 H11A 109.4 . . ?
N1 C11 H11A 109.4 . . ?
N2 C11 H11B 109.4 . . ?
N1 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N2 C12 N3 112.3(13) . . ?
N2 C12 H12A 109.1 . . ?
N3 C12 H12A 109.1 . . ?
N2 C12 H12B 109.1 . . ?
N3 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
N4 C13 N1 111.5(13) . . ?
N4 C13 H13A 109.3 . . ?
N1 C13 H13A 109.3 . . ?
N4 C13 H13B 109.3 . . ?
N1 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
N4 C14 N2 113.3(14) . . ?
N4 C14 H14A 108.9 . . ?
N2 C14 H14A 108.9 . . ?
N4 C14 H14B 108.9 . . ?
N2 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
N3 C15 N4 111.1(13) . . ?
N3 C15 H15A 109.4 . . ?
N4 C15 H15A 109.4 . . ?
N3 C15 H15B 109.4 . . ?
N4 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C13 N1 C10 108.4(14) . . ?
C13 N1 C11 108.7(13) . . ?
C10 N1 C11 107.4(13) . . ?
C11 N2 C12 109.2(16) . . ?
C11 N2 C14 108.1(15) . . ?
C12 N2 C14 107.0(14) . . ?
C15 N3 C12 108.3(13) . . ?
C15 N3 C10 108.7(14) . . ?
C12 N3 C10 107.7(13) . . ?
C14 N4 C13 108.2(16) . . ?
C14 N4 C15 107.8(16) . . ?
C13 N4 C15 110.0(18) . . ?
C9 O1 H1A 111(10) . . ?

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
C8 C3 C4 C5 0(2) . . . . ?
C2 C3 C4 C5 -176.8(15) . . . . ?
C3 C4 C5 C6 1(3) . . . . ?
C4 C5 C6 C7 -2(2) . . . . ?
C5 C6 C7 C8 0(2) . . . . ?
C5 C6 C7 C9 178.6(14) . . . . ?
C6 C7 C8 C3 1(2) . . . . ?
C9 C7 C8 C3 -177.1(13) . . . . ?
C4 C3 C8 C7 -1(2) . . . . ?
C2 C3 C8 C7 175.7(14) . . . . ?
C8 C7 C9 O2 -178.7(16) . . . . ?
C6 C7 C9 O2 3(3) . . . . ?
C8 C7 C9 O1 1(2) . . . . ?
C6 C7 C9 O1 -176.7(15) . . . . ?
N4 C13 N1 C10 -58(2) . . . . ?
N4 C13 N1 C11 58.3(19) . . . . ?
N3 C10 N1 C13 57.8(19) . . . . ?
N3 C10 N1 C11 -59.5(18) . . . . ?
N2 C11 N1 C13 -57.7(17) . . . . ?
N2 C11 N1 C10 59.4(18) . . . . ?
N1 C11 N2 C12 -59.2(19) . . . . ?
N1 C11 N2 C14 57(2) . . . . ?
N3 C12 N2 C11 59(2) . . . . ?
N3 C12 N2 C14 -58(2) . . . . ?
N4 C14 N2 C11 -59(2) . . . . ?
N4 C14 N2 C12 58(2) . . . . ?
N4 C15 N3 C12 -59(2) . . . . ?
N4 C15 N3 C10 58(2) . . . . ?
N2 C12 N3 C15 59.3(18) . . . . ?
N2 C12 N3 C10 -58.1(19) . . . . ?
N1 C10 N3 C15 -58.2(18) . . . . ?
N1 C10 N3 C12 58.9(18) . . . . ?
N2 C14 N4 C13 60(2) . . . . ?
N2 C14 N4 C15 -59(2) . . . . ?
N1 C13 N4 C14 -59(2) . . . . ?
N1 C13 N4 C15 59(2) . . . . ?
N3 C15 N4 C14 59(2) . . . . ?
N3 C15 N4 C13 -59(2) . . . . ?

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
C14 H14A O2 0.99 2.43 3.37(2) 158.4 .
C14 H14B I1 0.99 3.06 4.038(19) 170.7 1_655
O1 H1A N1 0.9(2) 1.7(2) 2.617(17) 169(19) 1_556

_refine_diff_density_max         2.072
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.156


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1817908'
_audit_update_record             
;
2018-01-18 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        (3-iodoethynylbenzoate)(piperazinium)
_chemical_name_common            '(3-iodoethynylbenzoic acid)(piperazine)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H4 I1 O2, C4 H11 N2'
_chemical_formula_sum            'C13 H15 I N2 O2'
_chemical_formula_weight         358.17

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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

_cell_length_a                   15.2720(4)
_cell_length_b                   6.6017(2)
_cell_length_c                   28.5827(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.9710(10)
_cell_angle_gamma                90
_cell_volume                     2783.92(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9817
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      29.55
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.394
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.166
_exptl_absorpt_coefficient_mu    2.297
_shelx_estimated_absorpt_T_min   0.465
_shelx_estimated_absorpt_T_max   0.702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6394
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44592
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.475
_diffrn_reflns_theta_max         29.772
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3886
_reflns_number_gt                3430
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX II (Bruker, 2009)'
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'XT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0109P)²+5.5461P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3886
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0568
_refine_ls_wR_factor_gt          0.0546
_refine_ls_goodness_of_fit_ref   1.361
_refine_ls_restrained_S_all      1.361
_refine_ls_shift/su_max          0.005
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.63050(19) 0.3749(4) 0.49933(9) 0.0380(6) Uani 1 1 d . . . . .
C2 C 0.58786(18) 0.2614(4) 0.46990(9) 0.0354(6) Uani 1 1 d . . . . .
C3 C 0.53681(16) 0.1265(4) 0.43310(9) 0.0294(5) Uani 1 1 d . . . . .
C4 C 0.52582(17) -0.0783(4) 0.44274(9) 0.0336(5) Uani 1 1 d . . . . .
H4 H 0.551886 -0.131543 0.474136 0.040 Uiso 1 1 calc R U . . .
C5 C 0.47674(17) -0.2036(4) 0.40634(9) 0.0331(5) Uani 1 1 d . . . . .
H5 H 0.469258 -0.342630 0.412964 0.040 Uiso 1 1 calc R U . . .
C6 C 0.43859(16) -0.1276(4) 0.36044(9) 0.0295(5) Uani 1 1 d . . . . .
H6 H 0.406008 -0.215182 0.335622 0.035 Uiso 1 1 calc R U . . .
C7 C 0.44782(15) 0.0771(4) 0.35051(8) 0.0275(5) Uani 1 1 d . . . . .
C8 C 0.49719(15) 0.2011(4) 0.38671(8) 0.0279(5) Uani 1 1 d . . . . .
H8 H 0.504385 0.340033 0.379928 0.033 Uiso 1 1 calc R U . . .
C9 C 0.40274(16) 0.1683(4) 0.30170(9) 0.0319(5) Uani 1 1 d . . . . .
C10 C 0.3792(2) 0.6829(4) 0.20813(10) 0.0423(6) Uani 1 1 d . . . . .
H10A H 0.441955 0.650463 0.207045 0.051 Uiso 1 1 calc R U . . .
H10B H 0.382210 0.765981 0.237339 0.051 Uiso 1 1 calc R U . . .
C11 C 0.33226(19) 0.8007(4) 0.16342(10) 0.0400(6) Uani 1 1 d . . . . .
H11A H 0.272688 0.847325 0.166952 0.048 Uiso 1 1 calc R U . . .
H11B H 0.368804 0.922267 0.161067 0.048 Uiso 1 1 calc R U . . .
C12 C 0.27553(18) 0.4909(4) 0.12163(9) 0.0354(6) Uani 1 1 d . . . . .
H12A H 0.277072 0.409897 0.092704 0.042 Uiso 1 1 calc R U . . .
H12B H 0.211125 0.514153 0.120848 0.042 Uiso 1 1 calc R U . . .
C13 C 0.3195(2) 0.3694(4) 0.16656(10) 0.0382(6) Uani 1 1 d . . . . .
H13A H 0.282009 0.248581 0.168286 0.046 Uiso 1 1 calc R U . . .
H13B H 0.379976 0.322387 0.164616 0.046 Uiso 1 1 calc R U . . .
N1 N 0.32901(17) 0.4934(4) 0.21077(8) 0.0358(5) Uani 1 1 d . . . . .
N2 N 0.31827(15) 0.6852(4) 0.11869(8) 0.0341(5) Uani 1 1 d . . . . .
O1 O 0.33968(12) 0.0722(3) 0.27385(6) 0.0408(4) Uani 1 1 d . . . . .
O2 O 0.43068(15) 0.3387(3) 0.29298(7) 0.0527(6) Uani 1 1 d . . . . .
I1 I 0.70779(2) 0.56347(3) 0.54892(2) 0.03530(6) Uani 1 1 d . . . . .
H1A H 0.362(2) 0.420(5) 0.2395(13) 0.058(10) Uiso 1 1 d . . . . .
H1B H 0.276(2) 0.513(5) 0.2149(11) 0.040(8) Uiso 1 1 d . . . . .
H2A H 0.368(2) 0.676(5) 0.1129(10) 0.038(8) Uiso 1 1 d . . . . .


_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
C1 C2 1.187(4) . ?
C1 I1 2.022(3) . ?
C2 C3 1.444(4) . ?
C3 C8 1.397(3) . ?
C3 C4 1.399(4) . ?
C4 C5 1.388(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(3) . ?
C7 C9 1.512(3) . ?
C8 H8 0.9500 . ?
C9 O2 1.251(3) . ?
C9 O1 1.252(3) . ?
C10 N1 1.480(4) . ?
C10 C11 1.509(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N2 1.456(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N2 1.451(3) . ?
C12 C13 1.516(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N1 1.481(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
N1 H1A 0.98(4) . ?
N1 H1B 0.86(3) . ?
N2 H2A 0.82(3) . ?

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 I1 177.7(3) . . ?
C1 C2 C3 178.4(3) . . ?
C8 C3 C4 118.9(2) . . ?
C8 C3 C2 119.6(2) . . ?
C4 C3 C2 121.5(2) . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.2(2) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 119.1(2) . . ?
C8 C7 C9 119.0(2) . . ?
C6 C7 C9 121.8(2) . . ?
C7 C8 C3 121.4(2) . . ?
C7 C8 H8 119.3 . . ?
C3 C8 H8 119.3 . . ?
O2 C9 O1 125.1(2) . . ?
O2 C9 C7 116.4(2) . . ?
O1 C9 C7 118.5(2) . . ?
N1 C10 C11 109.8(2) . . ?
N1 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
N1 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N2 C11 C10 113.8(2) . . ?
N2 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
N2 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
N2 C12 C13 114.2(2) . . ?
N2 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
N2 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
N1 C13 C12 110.8(2) . . ?
N1 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C10 N1 C13 111.2(2) . . ?
C10 N1 H1A 108(2) . . ?
C13 N1 H1A 111(2) . . ?
C10 N1 H1B 114(2) . . ?
C13 N1 H1B 108(2) . . ?
H1A N1 H1B 105(3) . . ?
C12 N2 C11 112.2(2) . . ?
C12 N2 H2A 114(2) . . ?
C11 N2 H2A 106(2) . . ?

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
C8 C3 C4 C5 0.5(4) . . . . ?
C2 C3 C4 C5 -179.6(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
C5 C6 C7 C8 1.5(3) . . . . ?
C5 C6 C7 C9 -176.5(2) . . . . ?
C6 C7 C8 C3 -1.0(3) . . . . ?
C9 C7 C8 C3 177.1(2) . . . . ?
C4 C3 C8 C7 0.0(4) . . . . ?
C2 C3 C8 C7 -180.0(2) . . . . ?
C8 C7 C9 O2 17.2(3) . . . . ?
C6 C7 C9 O2 -164.8(2) . . . . ?
C8 C7 C9 O1 -161.1(2) . . . . ?
C6 C7 C9 O1 16.9(4) . . . . ?
N1 C10 C11 N2 -54.9(3) . . . . ?
N2 C12 C13 N1 51.5(3) . . . . ?
C11 C10 N1 C13 56.7(3) . . . . ?
C12 C13 N1 C10 -55.2(3) . . . . ?
C13 C12 N2 C11 -49.0(3) . . . . ?
C10 C11 N2 C12 50.9(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
C10 H10B O1 0.99 2.44 3.329(4) 149.4 1_565
N1 H1A O1 0.98(4) 2.55(4) 3.295(3) 133(3) .
N1 H1A O2 0.98(4) 1.70(4) 2.663(3) 168(3) .
N1 H1B O1 0.86(3) 1.91(3) 2.772(3) 176(3) 4

_refine_diff_density_max         0.841
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.077


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
