# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_r11018_a
_database_code_depnum_ccdc_archive 'CCDC 1879535'
_audit_update_record             
;
2018-11-16 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            
'Cocrystal between 1,2-bis(iodoethynyl)benzene and 4-stilbazole'
_chemical_melting_point          ?
_chemical_formula_moiety         '0.5(C10 H4 I2), C13 H11 N'
_chemical_formula_sum            'C18 H13 I N'
_chemical_formula_weight         370.19

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'
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        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   17.008(2)
_cell_length_b                   10.0083(10)
_cell_length_c                   19.248(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.513(10)
_cell_angle_gamma                90
_cell_volume                     3106.9(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    9834
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      28.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_F_000             1448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.147
_exptl_crystal_size_mid          0.328
_exptl_crystal_size_max          0.369
_exptl_absorpt_coefficient_mu    2.051
_shelx_estimated_absorpt_T_min   0.518
_shelx_estimated_absorpt_T_max   0.753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4901
_exptl_absorpt_correction_T_max  0.5644
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(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            46317
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.232
_diffrn_reflns_theta_max         30.580
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4775
_reflns_number_gt                3574
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'XSeed (Barbour, 2001)'

_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)+(0.0287P)²+2.8788P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4775
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0707
_refine_ls_wR_factor_gt          0.0619
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
I1 I 0.42827(2) 0.53341(2) 0.60009(2) 0.05830(7) Uani 1 1 d . . . . .
N1 N 0.50807(14) 0.2886(2) 0.62628(13) 0.0690(6) Uani 1 1 d . . . . .
C16 C 0.28856(14) 0.9326(2) 0.52806(13) 0.0514(5) Uani 1 1 d . . . . .
C15 C 0.32984(15) 0.8092(2) 0.55482(14) 0.0572(5) Uani 1 1 d . . . . .
C14 C 0.36627(15) 0.7078(2) 0.57431(14) 0.0606(6) Uani 1 1 d . . . . .
C17 C 0.32552(17) 1.0537(2) 0.55540(16) 0.0622(6) Uani 1 1 d . . . . .
H17 H 0.376273 1.054605 0.592568 0.075 Uiso 1 1 calc R U . . .
C8 C 0.65436(14) -0.3277(3) 0.68209(15) 0.0618(6) Uani 1 1 d . . . . .
C5 C 0.57428(16) 0.0315(3) 0.63124(16) 0.0633(6) Uani 1 1 d . . . . .
C18 C 0.28734(17) 1.1728(2) 0.52770(16) 0.0691(7) Uani 1 1 d . . . . .
H18 H 0.312252 1.253409 0.546607 0.083 Uiso 1 1 calc R U . . .
C7 C 0.62329(16) -0.1909(3) 0.68226(16) 0.0673(6) Uani 1 1 d . . . . .
H7 H 0.615241 -0.162675 0.725539 0.081 Uiso 1 1 calc R U . . .
C13 C 0.66898(18) -0.3865(3) 0.62265(18) 0.0752(7) Uani 1 1 d . . . . .
H13 H 0.658724 -0.338311 0.579352 0.090 Uiso 1 1 calc R U . . .
C4 C 0.5574(2) 0.0865(3) 0.69089(16) 0.0786(8) Uani 1 1 d . . . . .
H4 H 0.568109 0.038005 0.734114 0.094 Uiso 1 1 calc R U . . .
C2 C 0.52566(18) 0.2364(3) 0.57028(17) 0.0733(7) Uani 1 1 d . . . . .
H2 H 0.515269 0.287450 0.527956 0.088 Uiso 1 1 calc R U . . .
C3 C 0.52472(19) 0.2135(3) 0.68606(16) 0.0772(8) Uani 1 1 d . . . . .
H3 H 0.513748 0.248387 0.726812 0.093 Uiso 1 1 calc R U . . .
C1 C 0.55829(18) 0.1116(3) 0.57054(17) 0.0729(7) Uani 1 1 d . . . . .
H1 H 0.569744 0.080679 0.529211 0.088 Uiso 1 1 calc R U . . .
C6 C 0.60576(18) -0.1048(3) 0.62930(16) 0.0727(7) Uani 1 1 d . . . . .
H6 H 0.613879 -0.131769 0.585845 0.087 Uiso 1 1 calc R U . . .
C9 C 0.66975(19) -0.4020(3) 0.74506(17) 0.0775(8) Uani 1 1 d . . . . .
H9 H 0.660752 -0.364427 0.786074 0.093 Uiso 1 1 calc R U . . .
C12 C 0.6985(2) -0.5150(3) 0.6262(2) 0.0829(8) Uani 1 1 d . . . . .
H12 H 0.708714 -0.552600 0.585719 0.099 Uiso 1 1 calc R U . . .
C11 C 0.7127(2) -0.5874(3) 0.6891(2) 0.0883(9) Uani 1 1 d . . . . .
H11 H 0.732139 -0.674639 0.691478 0.106 Uiso 1 1 calc R U . . .
C10 C 0.6982(2) -0.5310(3) 0.7483(2) 0.0943(11) Uani 1 1 d . . . . .
H10 H 0.707688 -0.580144 0.791147 0.113 Uiso 1 1 calc R U . . .


_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 C14 2.018(3) . ?
N1 C2 1.315(4) . ?
N1 C3 1.327(4) . ?
C16 C17 1.390(3) . ?
C16 C16 1.410(5) 2_556 ?
C16 C15 1.432(3) . ?
C15 C14 1.186(3) . ?
C17 C18 1.381(4) . ?
C8 C9 1.374(4) . ?
C8 C13 1.378(4) . ?
C8 C7 1.468(4) . ?
C5 C1 1.371(4) . ?
C5 C4 1.383(4) . ?
C5 C6 1.470(4) . ?
C18 C18 1.375(6) 2_556 ?
C7 C6 1.295(4) . ?
C13 C12 1.374(4) . ?
C4 C3 1.379(4) . ?
C2 C1 1.366(4) . ?
C9 C10 1.373(5) . ?
C12 C11 1.365(5) . ?
C11 C10 1.362(5) . ?

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 N1 C3 116.4(2) . . ?
C17 C16 C16 119.27(15) . 2_556 ?
C17 C16 C15 120.3(2) . . ?
C16 C16 C15 120.40(14) 2_556 . ?
C14 C15 C16 176.5(3) . . ?
C15 C14 I1 175.9(2) . . ?
C18 C17 C16 120.4(3) . . ?
C9 C8 C13 117.9(3) . . ?
C9 C8 C7 118.1(3) . . ?
C13 C8 C7 124.1(3) . . ?
C1 C5 C4 115.9(2) . . ?
C1 C5 C6 119.7(3) . . ?
C4 C5 C6 124.3(3) . . ?
C18 C18 C17 120.33(16) 2_556 . ?
C6 C7 C8 127.7(3) . . ?
C12 C13 C8 121.2(3) . . ?
C3 C4 C5 119.8(3) . . ?
N1 C2 C1 123.9(3) . . ?
N1 C3 C4 123.4(3) . . ?
C2 C1 C5 120.5(3) . . ?
C7 C6 C5 126.3(3) . . ?
C10 C9 C8 120.9(3) . . ?
C11 C12 C13 120.0(3) . . ?
C10 C11 C12 119.6(3) . . ?
C11 C10 C9 120.4(3) . . ?

_refine_diff_density_max         0.797
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.057

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_r13918_a
_database_code_depnum_ccdc_archive 'CCDC 1879537'
_audit_update_record             
;
2018-11-16 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            
'Cocrystal between 1,2-bis(iodoethynyl)benzene and trans-1,2-bis(4-pyridyl)ethyne'

_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H4 I2, 2(C6 H4 N)'
_chemical_formula_sum            'C22 H12 I2 N2'
_chemical_formula_weight         558.14

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'
I I -0.4742 1.8119 '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                   7.5641(12)
_cell_length_b                   8.3619(12)
_cell_length_c                   17.500(3)
_cell_angle_alpha                94.126(8)
_cell_angle_beta                 96.466(8)
_cell_angle_gamma                106.153(7)
_cell_volume                     1050.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9714
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      29.70

_exptl_crystal_description       rectangular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.291
_exptl_crystal_size_min          0.159
_exptl_absorpt_coefficient_mu    3.001
_shelx_estimated_absorpt_T_min   0.418
_shelx_estimated_absorpt_T_max   0.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5121
_exptl_absorpt_correction_T_max  0.6480
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number            25799
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.178
_diffrn_reflns_theta_max         31.086
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6714
_reflns_number_gt                4590
_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       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)²+0.3069P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6714
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0958
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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_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 -0.03809(3) 0.61490(2) 0.13100(2) 0.06289(8) Uani 1 1 d . . . . .
N1 N -0.4015(4) 0.4057(3) 0.07703(17) 0.0651(7) Uani 1 1 d . . . . .
C1 C -0.5439(5) 0.4044(4) 0.1139(2) 0.0718(9) Uani 1 1 d . . . . .
H1 H -0.526151 0.484985 0.155764 0.086 Uiso 1 1 calc R U . . .
I2 I 0.47319(3) 0.35547(3) 0.37720(2) 0.06882(9) Uani 1 1 d . . . . .
N2 N 0.3256(4) 0.0477(4) 0.43824(17) 0.0674(7) Uani 1 1 d . . . . .
C2 C -0.7181(4) 0.2912(4) 0.0947(2) 0.0686(8) Uani 1 1 d . . . . .
H2 H -0.813304 0.295605 0.123305 0.082 Uiso 1 1 calc R U . . .
C3 C -0.7487(4) 0.1724(4) 0.03268(18) 0.0572(7) Uani 1 1 d . . . . .
C4 C -0.6014(5) 0.1749(4) -0.0073(2) 0.0700(9) Uani 1 1 d . . . . .
H4 H -0.616175 0.098432 -0.050500 0.084 Uiso 1 1 calc R U . . .
C5 C -0.4317(5) 0.2916(4) 0.0172(2) 0.0698(8) Uani 1 1 d . . . . .
H5 H -0.333205 0.289718 -0.009883 0.084 Uiso 1 1 calc R U . . .
C6 C -0.9273(5) 0.0505(4) 0.0095(2) 0.0676(8) Uani 1 1 d . . . . .
C7 C 0.2264(4) 0.7499(4) 0.17253(18) 0.0613(7) Uani 1 1 d . . . . .
C8 C 0.3827(4) 0.8246(4) 0.19601(17) 0.0566(7) Uani 1 1 d . . . . .
C9 C 0.5727(4) 0.9164(4) 0.22124(16) 0.0530(6) Uani 1 1 d . . . . .
C10 C 0.6445(5) 1.0767(4) 0.1973(2) 0.0741(9) Uani 1 1 d . . . . .
H10 H 0.567479 1.123449 0.166693 0.089 Uiso 1 1 calc R U . . .
C11 C 0.8279(7) 1.1631(5) 0.2192(3) 0.0967(14) Uani 1 1 d . . . . .
H11 H 0.874215 1.269642 0.204308 0.116 Uiso 1 1 calc R U . . .
C12 C 0.9444(6) 1.0942(6) 0.2630(3) 0.0952(13) Uani 1 1 d . . . . .
H12 H 1.069813 1.152320 0.275228 0.114 Uiso 1 1 calc R U . . .
C13 C 0.8784(5) 0.9424(5) 0.2886(2) 0.0774(10) Uani 1 1 d . . . . .
H13 H 0.958098 0.898780 0.319408 0.093 Uiso 1 1 calc R U . . .
C14 C 0.6897(4) 0.8505(4) 0.26881(17) 0.0544(6) Uani 1 1 d . . . . .
C15 C 0.6214(4) 0.6941(4) 0.29916(18) 0.0590(7) Uani 1 1 d . . . . .
C16 C 0.5693(5) 0.5687(4) 0.32790(19) 0.0667(8) Uani 1 1 d . . . . .
C17 C 0.2537(5) 0.0251(5) 0.5031(2) 0.0767(9) Uani 1 1 d . . . . .
H17 H 0.265226 0.119083 0.537230 0.092 Uiso 1 1 calc R U . . .
C18 C 0.1627(5) -0.1287(5) 0.5234(2) 0.0780(10) Uani 1 1 d . . . . .
H18 H 0.115910 -0.137044 0.570366 0.094 Uiso 1 1 calc R U . . .
C19 C 0.1410(4) -0.2702(4) 0.4741(2) 0.0621(8) Uani 1 1 d . . . . .
C20 C 0.2187(5) -0.2492(4) 0.4068(2) 0.0713(9) Uani 1 1 d . . . . .
H20 H 0.210585 -0.341086 0.371880 0.086 Uiso 1 1 calc R U . . .
C21 C 0.3088(5) -0.0892(5) 0.3920(2) 0.0750(9) Uani 1 1 d . . . . .
H21 H 0.361142 -0.076936 0.346340 0.090 Uiso 1 1 calc R U . . .
C22 C 0.0413(5) -0.4341(4) 0.4922(2) 0.0711(9) Uani 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 C7 2.025(3) . ?
N1 C1 1.315(5) . ?
N1 C5 1.319(4) . ?
C1 C2 1.380(5) . ?
I2 C16 2.023(3) . ?
N2 C17 1.317(5) . ?
N2 C21 1.321(5) . ?
C2 C3 1.370(5) . ?
C3 C4 1.377(5) . ?
C3 C6 1.442(4) . ?
C4 C5 1.379(5) . ?
C6 C6 1.181(6) 2_355 ?
C7 C8 1.183(4) . ?
C8 C9 1.430(4) . ?
C9 C14 1.397(4) . ?
C9 C10 1.412(4) . ?
C10 C11 1.370(6) . ?
C11 C12 1.374(7) . ?
C12 C13 1.357(6) . ?
C13 C14 1.410(4) . ?
C14 C15 1.430(4) . ?
C15 C16 1.182(4) . ?
C17 C18 1.372(5) . ?
C18 C19 1.373(5) . ?
C19 C20 1.376(5) . ?
C19 C22 1.445(5) . ?
C20 C21 1.380(5) . ?
C22 C22 1.174(7) 2_546 ?

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
C1 N1 C5 116.5(3) . . ?
N1 C1 C2 124.3(3) . . ?
C17 N2 C21 116.1(3) . . ?
C3 C2 C1 119.0(3) . . ?
C2 C3 C4 117.1(3) . . ?
C2 C3 C6 121.8(3) . . ?
C4 C3 C6 121.1(3) . . ?
C3 C4 C5 119.5(3) . . ?
N1 C5 C4 123.5(3) . . ?
C6 C6 C3 179.3(6) 2_355 . ?
C8 C7 I1 178.0(3) . . ?
C7 C8 C9 177.7(3) . . ?
C14 C9 C10 119.1(3) . . ?
C14 C9 C8 121.4(3) . . ?
C10 C9 C8 119.5(3) . . ?
C11 C10 C9 119.8(4) . . ?
C10 C11 C12 120.8(4) . . ?
C13 C12 C11 120.7(3) . . ?
C12 C13 C14 120.4(4) . . ?
C9 C14 C13 119.0(3) . . ?
C9 C14 C15 121.5(3) . . ?
C13 C14 C15 119.5(3) . . ?
C16 C15 C14 176.6(3) . . ?
C15 C16 I2 178.4(3) . . ?
N2 C17 C18 124.0(4) . . ?
C17 C18 C19 119.7(3) . . ?
C18 C19 C20 117.1(3) . . ?
C18 C19 C22 121.5(3) . . ?
C20 C19 C22 121.5(3) . . ?
C19 C20 C21 118.8(3) . . ?
N2 C21 C20 124.4(3) . . ?
C22 C22 C19 178.9(6) 2_546 . ?

_refine_diff_density_max         0.830
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.079





_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_r12118_a
_database_code_depnum_ccdc_archive 'CCDC 1879536'
_audit_update_record             
;
2018-11-16 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            
'Cocrystal between 1,2-bis(iodoethynyl)benzene and trans-1,2-bis(4-pyridyl)ethene'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H4 I2, C12 H10 N2'
_chemical_formula_sum            'C22 H14 I2 N2'
_chemical_formula_weight         560.15

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'
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                   12.8031(15)
_cell_length_b                   9.5117(13)
_cell_length_c                   17.856(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.973(8)
_cell_angle_gamma                90
_cell_volume                     2068.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    703
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      18.13
_cell_measurement_theta_min      2.40

_exptl_crystal_description       rod
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.071
_exptl_absorpt_coefficient_mu    3.048
_shelx_estimated_absorpt_T_max   0.813
_shelx_estimated_absorpt_T_min   0.551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6100
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number            6169
_diffrn_reflns_av_unetI/netI     0.1326
_diffrn_reflns_av_R_equivalents  0.1041
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.398
_diffrn_reflns_theta_max         25.150
_diffrn_reflns_theta_full        25.150
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1860
_reflns_number_gt                782
_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       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1259P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1860
_refine_ls_number_parameters     118
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.2029
_refine_ls_R_factor_gt           0.0862
_refine_ls_wR_factor_ref         0.2472
_refine_ls_wR_factor_gt          0.1880
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.965
_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 0.37071(10) 0.47372(13) 0.37690(8) 0.0760(6) Uani 1 1 d . U . . .
N1 N 0.3181(13) 0.2102(16) 0.4318(10) 0.078(4) Uani 1 1 d . U . . .
C1 C 0.3786(17) 0.135(2) 0.4924(12) 0.091(6) Uani 1 1 d . U . . .
H1 H 0.442577 0.175567 0.525087 0.109 Uiso 1 1 calc R U . . .
C2 C 0.3528(16) 0.000(2) 0.5102(13) 0.084(5) Uani 1 1 d . U . . .
H2 H 0.395313 -0.046583 0.555009 0.101 Uiso 1 1 calc R U . . .
C3 C 0.2601(17) -0.062(2) 0.4580(12) 0.079(5) Uani 1 1 d . U . . .
C4 C 0.2016(15) 0.0100(19) 0.3973(12) 0.074(5) Uani 1 1 d . U . . .
H4 H 0.139843 -0.029815 0.361597 0.089 Uiso 1 1 calc R U . . .
C5 C 0.2318(15) 0.144(2) 0.3866(12) 0.086(6) Uani 1 1 d . U . . .
H5 H 0.187167 0.193352 0.343477 0.103 Uiso 1 1 calc R U . . .
C6 C 0.229(2) -0.212(2) 0.4728(13) 0.096(7) Uani 1 1 d . U . . .
H6 H 0.170363 -0.250696 0.433809 0.115 Uiso 1 1 calc R U . . .
C7 C 0.4094(15) 0.653(2) 0.3327(11) 0.078(5) Uani 1 1 d . U . . .
C8 C 0.4352(18) 0.755(2) 0.3044(12) 0.081(6) Uani 1 1 d . U . . .
C9 C 0.4664(12) 0.8826(17) 0.2753(9) 0.056(4) Uani 1 1 d . U . . .
C10 C 0.4332(19) 1.0077(18) 0.2980(12) 0.083(6) Uani 1 1 d . U . . .
H10 H 0.387382 1.009209 0.329552 0.099 Uiso 1 1 calc R U . . .
C11 C 0.4684(19) 1.1319(19) 0.2736(12) 0.097(8) Uani 1 1 d . U . . .
H11 H 0.447659 1.217133 0.290250 0.117 Uiso 1 1 calc R U . . .


_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 C7 2.003(19) . ?
N1 C5 1.31(2) . ?
N1 C1 1.33(2) . ?
C1 C2 1.39(3) . ?
C2 C3 1.40(3) . ?
C3 C4 1.31(3) . ?
C3 C6 1.53(3) . ?
C4 C5 1.37(2) . ?
C6 C6 1.19(3) 7_546 ?
C7 C8 1.19(2) . ?
C8 C9 1.43(2) . ?
C9 C10 1.37(2) . ?
C9 C9 1.43(3) 2_655 ?
C10 C11 1.38(2) . ?
C11 C11 1.34(4) 2_655 ?

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
C5 N1 C1 114.4(19) . . ?
N1 C1 C2 124(2) . . ?
C1 C2 C3 117.0(18) . . ?
C4 C3 C2 118.9(19) . . ?
C4 C3 C6 122(2) . . ?
C2 C3 C6 119.5(19) . . ?
C3 C4 C5 120(2) . . ?
N1 C5 C4 125.6(19) . . ?
C6 C6 C3 129(4) 7_546 . ?
C8 C7 I1 176.5(16) . . ?
C7 C8 C9 176(2) . . ?
C10 C9 C8 119.0(15) . . ?
C10 C9 C9 119.4(11) . 2_655 ?
C8 C9 C9 121.5(9) . 2_655 ?
C9 C10 C11 119.3(19) . . ?
C11 C11 C10 121.3(11) 2_655 . ?

_refine_diff_density_max         2.069
_refine_diff_density_min         -0.714
_refine_diff_density_rms         0.185

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
