# 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_eb496_a
_database_code_depnum_ccdc_archive 'CCDC 1820039'
_audit_update_record             
;
2018-03-16 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1

_chemical_name_systematic        ?
_chemical_name_common            
;
Co-crystal between 1-iodo-3,5-dinitrobenzene and 4-(N,N-dimethylamino)pyridine
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H3 I N2 O4, C7 H10 N2'
_chemical_formula_sum            'C13 H13 I N4 O4'
_chemical_formula_weight         416.17

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           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                   7.1573(3)
_cell_length_b                   16.8141(7)
_cell_length_c                   12.5916(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.9050(10)
_cell_angle_gamma                90
_cell_volume                     1492.73(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8614
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.10

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.852
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.169
_shelx_estimated_absorpt_T_min   0.860
_shelx_estimated_absorpt_T_max   1.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8598
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS V2014 (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3660

_diffrn_reflns_number            19222
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.040
_diffrn_reflns_theta_max         27.104
_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             3298
_reflns_number_gt                2960
_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       'SMART, Bruker, 2014'
_computing_cell_refinement       'SMART, Bruker, 2014'
_computing_data_reduction        'SAINT, Bruker, 2014'
_computing_structure_solution    'SHELXT 2014/6 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_molecular_graphics    'XSeed (Barbour, 2001)'
_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)+(0.0154P)²+1.3952P] 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         3298
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0180
_refine_ls_wR_factor_ref         0.0421
_refine_ls_wR_factor_gt          0.0400
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.004
_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 0.29382(2) 0.75308(2) 0.55676(2) 0.01324(4) Uani 1 1 d . . . . .
O1 O 0.7568(2) 0.69417(9) 0.95065(12) 0.0273(3) Uani 1 1 d . . . . .
N1 N 0.0986(2) 0.66222(10) 0.37600(13) 0.0170(3) Uani 1 1 d . . . . .
C1 C 0.0111(3) 0.67322(11) 0.27367(15) 0.0155(4) Uani 1 1 d . . . . .
H1 H 0.001825 0.726177 0.246987 0.019 Uiso 1 1 calc R U . . .
O2 O 0.7942(2) 0.80202(10) 1.04618(11) 0.0239(3) Uani 1 1 d . . . . .
N2 N -0.1407(3) 0.47333(10) 0.17895(14) 0.0256(4) Uani 1 1 d . . . . .
C2 C -0.0662(3) 0.61384(11) 0.20452(15) 0.0142(4) Uani 1 1 d . . . . .
H2 H -0.124627 0.626228 0.132876 0.017 Uiso 1 1 calc R U . . .
O3 O 0.5337(2) 1.04992(9) 0.88917(13) 0.0309(4) Uani 1 1 d . . . . .
N3 N 0.7339(2) 0.76548(10) 0.96319(13) 0.0179(3) Uani 1 1 d . . . . .
C3 C -0.0577(3) 0.53451(11) 0.24105(15) 0.0150(4) Uani 1 1 d . . . . .
O4 O 0.4008(2) 1.05296(9) 0.72183(12) 0.0269(3) Uani 1 1 d . . . . .
N4 N 0.4774(2) 1.01783(10) 0.80307(14) 0.0194(4) Uani 1 1 d . . . . .
C4 C 0.0366(3) 0.52171(12) 0.34761(15) 0.0158(4) Uani 1 1 d . . . . .
H4 H 0.049931 0.469430 0.376541 0.019 Uiso 1 1 calc R U . . .
C5 C 0.1092(3) 0.58608(12) 0.40934(16) 0.0173(4) Uani 1 1 d . . . . .
H5 H 0.171496 0.575805 0.480902 0.021 Uiso 1 1 calc R U . . .
C6 C -0.2419(3) 0.48717(14) 0.07041(17) 0.0263(5) Uani 1 1 d . . . . .
H6A H -0.314495 0.536703 0.068731 0.039 Uiso 1 1 calc R U . . .
H6B H -0.328674 0.442776 0.048410 0.039 Uiso 1 1 calc R U . . .
H6C H -0.150839 0.491368 0.020775 0.039 Uiso 1 1 calc R U . . .
C7 C -0.1045(4) 0.39126(12) 0.21332(19) 0.0290(5) Uani 1 1 d . . . . .
H7A H 0.032233 0.380894 0.224398 0.044 Uiso 1 1 calc R U . . .
H7B H -0.169714 0.355329 0.157738 0.044 Uiso 1 1 calc R U . . .
H7C H -0.151579 0.382321 0.280965 0.044 Uiso 1 1 calc R U . . .
C8 C 0.4362(3) 0.81058(11) 0.69593(14) 0.0129(4) Uani 1 1 d . . . . .
C9 C 0.5418(3) 0.76825(11) 0.78051(15) 0.0136(4) Uani 1 1 d . . . . .
H9 H 0.558090 0.712365 0.775743 0.016 Uiso 1 1 calc R U . . .
C10 C 0.6230(3) 0.81014(12) 0.87241(15) 0.0144(4) Uani 1 1 d . . . . .
C11 C 0.6040(3) 0.89113(11) 0.88402(15) 0.0148(4) Uani 1 1 d . . . . .
H11 H 0.658562 0.918173 0.948135 0.018 Uiso 1 1 calc R U . . .
C12 C 0.5008(3) 0.93074(11) 0.79684(15) 0.0142(4) Uani 1 1 d . . . . .
C13 C 0.4158(3) 0.89250(11) 0.70334(15) 0.0135(4) Uani 1 1 d . . . . .
H13 H 0.345061 0.921745 0.645450 0.016 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 C8 2.1045(18) . ?
O1 N3 1.224(2) . ?
N1 C1 1.345(2) . ?
N1 C5 1.345(3) . ?
C1 C2 1.377(3) . ?
C1 H1 0.9500 . ?
O2 N3 1.225(2) . ?
N2 C3 1.365(2) . ?
N2 C6 1.451(3) . ?
N2 C7 1.456(3) . ?
C2 C3 1.409(3) . ?
C2 H2 0.9500 . ?
O3 N4 1.216(2) . ?
N3 C10 1.479(2) . ?
C3 C4 1.411(3) . ?
O4 N4 1.226(2) . ?
N4 C12 1.478(2) . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.390(3) . ?
C8 C9 1.391(3) . ?
C9 C10 1.394(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(3) . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(3) . ?
C13 H13 0.9500 . ?

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 114.94(16) . . ?
N1 C1 C2 125.20(18) . . ?
N1 C1 H1 117.4 . . ?
C2 C1 H1 117.4 . . ?
C3 N2 C6 121.08(17) . . ?
C3 N2 C7 120.41(17) . . ?
C6 N2 C7 117.80(17) . . ?
C1 C2 C3 119.35(17) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
O1 N3 O2 124.46(17) . . ?
O1 N3 C10 117.62(16) . . ?
O2 N3 C10 117.91(17) . . ?
N2 C3 C2 122.44(17) . . ?
N2 C3 C4 121.31(18) . . ?
C2 C3 C4 116.21(17) . . ?
O3 N4 O4 124.21(18) . . ?
O3 N4 C12 117.64(17) . . ?
O4 N4 C12 118.14(16) . . ?
C5 C4 C3 119.20(18) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 125.08(18) . . ?
N1 C5 H5 117.5 . . ?
C4 C5 H5 117.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 120.34(17) . . ?
C13 C8 I1 118.03(13) . . ?
C9 C8 I1 121.59(14) . . ?
C8 C9 C10 118.11(17) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
C11 C10 C9 123.55(17) . . ?
C11 C10 N3 117.98(17) . . ?
C9 C10 N3 118.47(17) . . ?
C10 C11 C12 116.11(17) . . ?
C10 C11 H11 121.9 . . ?
C12 C11 H11 121.9 . . ?
C11 C12 C13 123.14(17) . . ?
C11 C12 N4 118.99(17) . . ?
C13 C12 N4 117.87(17) . . ?
C12 C13 C8 118.73(17) . . ?
C12 C13 H13 120.6 . . ?
C8 C13 H13 120.6 . . ?

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
_geom_hbond_publ_flag
C2 H2 O1 0.95 2.57 3.501(2) 165.5 1_454 yes
C5 H5 O3 0.95 2.48 3.333(2) 150.0 2_646 yes

_refine_diff_density_max         0.478
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_eb674_a
_database_code_depnum_ccdc_archive 'CCDC 1820041'
_audit_update_record             
;
2018-03-16 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1

_chemical_name_systematic        ?
_chemical_name_common            
;
Co-crystal between 3-[4-(N,N-dimethylamino) phenylethynyl] pyridine and 1-(3,5-dinitrophenylethynyl)-2,3,5,6-tetrafluoro-4-iodobenzene
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H3 F4 I N2 O4, C15 H14 N2'
_chemical_formula_sum            'C29 H17 F4 I N4 O4'
_chemical_formula_weight         688.36


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'
F F 0.0171 0.0103 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.2434(5)
_cell_length_b                   7.9376(5)
_cell_length_c                   47.215(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2714.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9131
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.40

_exptl_crystal_description       'cut rod'
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    1.251
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS V2014 (Bruker, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3660

_diffrn_reflns_number            34837
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -60
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_theta_min         1.725
_diffrn_reflns_theta_max         27.069
_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 1.000
_reflns_number_total             5977
_reflns_number_gt                5779
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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       'SMART, Bruker, 2014'
_computing_cell_refinement       'SMART, Bruker, 2014'
_computing_data_reduction        'SAINT, Bruker, 2014'
_computing_structure_solution    'SHELXT 2014/6 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_molecular_graphics    'XSeed (Barbour, 2001)'
_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)+5.6898P] 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_abs_structure_details 
;
 Flack x determined using 2286 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5977
_refine_ls_number_parameters     390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0724
_refine_ls_wR_factor_gt          0.0717
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_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 0.29549(5) 0.05615(5) 0.73498(2) 0.02186(9) Uani 1 1 d . . . . .
F1 F 0.4364(4) 0.2727(4) 0.62856(6) 0.0187(7) Uani 1 1 d . . . . .
O1 O 0.0861(6) 1.2959(5) 0.59861(8) 0.0221(9) Uani 1 1 d . . . . .
N1 N 0.2539(6) -0.1419(6) 0.78472(9) 0.0224(11) Uani 1 1 d . . . . .
C1 C 0.2490(6) -0.0426(8) 0.80743(11) 0.0205(12) Uani 1 1 d . . . . .
H1 H 0.286527 0.071314 0.805237 0.025 Uiso 1 1 calc R U . . .
F2 F 0.4242(4) 0.0402(4) 0.66915(6) 0.0217(7) Uani 1 1 d . . . . .
O2 O 0.2122(7) 1.3648(5) 0.55829(8) 0.0265(9) Uani 1 1 d . . . . .
N2 N 0.1853(8) 0.6626(5) 0.95431(9) 0.0222(10) Uani 1 1 d . . . . .
C2 C 0.2064(9) -0.3049(7) 0.78857(11) 0.0234(12) Uani 1 1 d . . . . .
H2 H 0.214886 -0.379592 0.772899 0.028 Uiso 1 1 calc R U . . .
F3 F 0.1741(4) 0.4420(5) 0.73220(6) 0.0301(7) Uani 1 1 d . . . . .
O3 O 0.4702(6) 0.9285(6) 0.49955(8) 0.0289(9) Uani 1 1 d . . . . .
N3 N 0.1758(7) 1.2623(6) 0.57748(10) 0.0203(11) Uani 1 1 d . . . . .
C3 C 0.1458(8) -0.3684(7) 0.81438(12) 0.0222(13) Uani 1 1 d . . . . .
H3 H 0.108762 -0.482811 0.816043 0.027 Uiso 1 1 calc R U . . .
F4 F 0.1733(5) 0.6705(4) 0.69106(7) 0.0292(8) Uani 1 1 d . . . . .
O4 O 0.5291(6) 0.6830(5) 0.51741(9) 0.0286(10) Uani 1 1 d . . . . .
N4 N 0.4667(6) 0.8268(6) 0.51903(10) 0.0195(10) Uani 1 1 d . . . . .
C4 C 0.1404(8) -0.2622(7) 0.83763(12) 0.0192(12) Uani 1 1 d . . . . .
H4 H 0.101781 -0.303186 0.855589 0.023 Uiso 1 1 calc R U . . .
C5 C 0.1921(8) -0.0954(6) 0.83432(10) 0.0164(11) Uani 1 1 d . . . . .
C6 C 0.1924(9) 0.0226(6) 0.85730(11) 0.0186(11) Uani 1 1 d . . . . .
C7 C 0.1931(8) 0.1276(6) 0.87542(11) 0.0174(10) Uani 1 1 d . . . . .
C8 C 0.1960(9) 0.2588(6) 0.89624(10) 0.0159(10) Uani 1 1 d . . . . .
C9 C 0.1287(7) 0.2364(7) 0.92383(11) 0.0148(11) Uani 1 1 d . . . . .
H9 H 0.080759 0.129678 0.929223 0.018 Uiso 1 1 calc R U . . .
C10 C 0.1307(7) 0.3661(7) 0.94335(11) 0.0152(11) Uani 1 1 d . . . . .
H10 H 0.088037 0.345780 0.962073 0.018 Uiso 1 1 calc R U . . .
C11 C 0.1946(8) 0.5277(6) 0.93602(10) 0.0147(10) Uani 1 1 d . . . . .
C12 C 0.2664(6) 0.5498(7) 0.90833(10) 0.0155(10) Uani 1 1 d . . . . .
H12 H 0.314777 0.656047 0.902804 0.019 Uiso 1 1 calc R U . . .
C13 C 0.2664(7) 0.4176(7) 0.88939(11) 0.0176(11) Uani 1 1 d . . . . .
H13 H 0.315948 0.435088 0.870998 0.021 Uiso 1 1 calc R U . . .
C14 C 0.1219(9) 0.6412(7) 0.98335(11) 0.0232(12) Uani 1 1 d . . . . .
H14A H 0.010294 0.571406 0.983502 0.035 Uiso 1 1 calc R U . . .
H14B H 0.094177 0.751634 0.991576 0.035 Uiso 1 1 calc R U . . .
H14C H 0.218637 0.585972 0.994513 0.035 Uiso 1 1 calc R U . . .
C15 C 0.2729(9) 0.8217(7) 0.94728(12) 0.0238(13) Uani 1 1 d . . . . .
H15A H 0.407376 0.808589 0.948027 0.036 Uiso 1 1 calc R U . . .
H15B H 0.234471 0.907974 0.960913 0.036 Uiso 1 1 calc R U . . .
H15C H 0.236090 0.856069 0.928162 0.036 Uiso 1 1 calc R U . . .
C16 C 0.3668(7) 0.3164(7) 0.65411(11) 0.0158(11) Uani 1 1 d . . . . .
C17 C 0.3638(7) 0.1968(7) 0.67528(11) 0.0159(11) Uani 1 1 d . . . . .
C18 C 0.3012(8) 0.2351(6) 0.70229(10) 0.0175(10) Uani 1 1 d . . . . .
C19 C 0.2395(7) 0.3967(7) 0.70663(11) 0.0188(12) Uani 1 1 d . . . . .
C20 C 0.2378(8) 0.5160(6) 0.68557(11) 0.0203(13) Uani 1 1 d . . . . .
C21 C 0.3041(8) 0.4798(6) 0.65850(10) 0.0161(10) Uani 1 1 d . . . . .
C22 C 0.3031(9) 0.6003(6) 0.63623(11) 0.0184(11) Uani 1 1 d . . . . .
C23 C 0.3022(8) 0.7009(6) 0.61737(11) 0.0194(11) Uani 1 1 d . . . . .
C24 C 0.3047(8) 0.8159(6) 0.59402(10) 0.0174(10) Uani 1 1 d . . . . .
C25 C 0.2374(7) 0.9805(7) 0.59701(11) 0.0162(11) Uani 1 1 d . . . . .
H25 H 0.189(9) 1.018(7) 0.6123(11) 0.019 Uiso 1 1 d . U . . .
C26 C 0.2472(6) 1.0890(6) 0.57429(11) 0.0156(12) Uani 1 1 d . . . . .
C27 C 0.3211(7) 1.0424(7) 0.54854(11) 0.0170(10) Uani 1 1 d . . . . .
H27 H 0.332(8) 1.114(7) 0.5356(12) 0.020 Uiso 1 1 d . U . . .
C28 C 0.3843(7) 0.8789(7) 0.54612(11) 0.0157(11) Uani 1 1 d . . . . .
C29 C 0.3785(8) 0.7651(7) 0.56822(12) 0.0163(11) Uani 1 1 d . . . . .
H29 H 0.421(8) 0.646(8) 0.5658(12) 0.020 Uiso 1 1 d . 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 C18 2.098(5) . ?
F1 C16 1.353(6) . ?
O1 N3 1.220(6) . ?
N1 C1 1.331(7) . ?
N1 C2 1.351(8) . ?
C1 C5 1.399(7) . ?
C1 H1 0.9500 . ?
F2 C17 1.349(6) . ?
O2 N3 1.246(6) . ?
N2 C11 1.378(6) . ?
N2 C15 1.452(7) . ?
N2 C14 1.456(7) . ?
C2 C3 1.390(8) . ?
C2 H2 0.9500 . ?
F3 C19 1.346(6) . ?
O3 N4 1.224(6) . ?
N3 C26 1.477(6) . ?
C3 C4 1.385(8) . ?
C3 H3 0.9500 . ?
F4 C20 1.338(6) . ?
O4 N4 1.230(6) . ?
N4 C28 1.470(7) . ?
C4 C5 1.385(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.433(7) . ?
C6 C7 1.194(7) . ?
C7 C8 1.432(7) . ?
C8 C13 1.397(7) . ?
C8 C9 1.402(7) . ?
C9 C10 1.382(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.407(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.418(7) . ?
C12 C13 1.378(7) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.378(7) . ?
C16 C21 1.390(7) . ?
C17 C18 1.387(7) . ?
C18 C19 1.374(7) . ?
C19 C20 1.373(7) . ?
C20 C21 1.395(7) . ?
C21 C22 1.422(7) . ?
C22 C23 1.195(7) . ?
C23 C24 1.432(7) . ?
C24 C29 1.390(8) . ?
C24 C25 1.401(7) . ?
C25 C26 1.378(7) . ?
C25 H25 0.85(6) . ?
C26 C27 1.379(7) . ?
C27 C28 1.381(8) . ?
C27 H27 0.84(6) . ?
C28 C29 1.381(8) . ?
C29 H29 1.00(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
C1 N1 C2 116.9(5) . . ?
N1 C1 C5 124.2(5) . . ?
N1 C1 H1 117.9 . . ?
C5 C1 H1 117.9 . . ?
C11 N2 C15 120.8(5) . . ?
C11 N2 C14 121.0(4) . . ?
C15 N2 C14 117.0(4) . . ?
N1 C2 C3 123.1(5) . . ?
N1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
O1 N3 O2 124.4(5) . . ?
O1 N3 C26 118.3(5) . . ?
O2 N3 C26 117.4(4) . . ?
C4 C3 C2 118.9(5) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
O3 N4 O4 123.9(5) . . ?
O3 N4 C28 118.5(5) . . ?
O4 N4 C28 117.7(5) . . ?
C3 C4 C5 119.0(5) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C1 117.9(5) . . ?
C4 C5 C6 122.7(5) . . ?
C1 C5 C6 119.4(5) . . ?
C7 C6 C5 176.5(5) . . ?
C6 C7 C8 177.6(6) . . ?
C13 C8 C9 117.1(5) . . ?
C13 C8 C7 120.1(5) . . ?
C9 C8 C7 122.7(5) . . ?
C10 C9 C8 121.4(5) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 121.2(5) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
N2 C11 C10 122.6(5) . . ?
N2 C11 C12 120.0(5) . . ?
C10 C11 C12 117.4(5) . . ?
C13 C12 C11 120.2(5) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 122.5(5) . . ?
C12 C13 H13 118.8 . . ?
C8 C13 H13 118.8 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
F1 C16 C17 118.4(5) . . ?
F1 C16 C21 119.6(5) . . ?
C17 C16 C21 122.0(5) . . ?
F2 C17 C16 118.3(5) . . ?
F2 C17 C18 120.3(5) . . ?
C16 C17 C18 121.4(5) . . ?
C19 C18 C17 116.6(5) . . ?
C19 C18 I1 121.1(4) . . ?
C17 C18 I1 122.3(4) . . ?
F3 C19 C20 117.5(5) . . ?
F3 C19 C18 119.8(5) . . ?
C20 C19 C18 122.6(5) . . ?
F4 C20 C19 119.7(5) . . ?
F4 C20 C21 119.1(5) . . ?
C19 C20 C21 121.2(5) . . ?
C16 C21 C20 116.2(4) . . ?
C16 C21 C22 121.3(5) . . ?
C20 C21 C22 122.5(5) . . ?
C23 C22 C21 179.6(6) . . ?
C22 C23 C24 177.5(6) . . ?
C29 C24 C25 119.5(5) . . ?
C29 C24 C23 119.6(5) . . ?
C25 C24 C23 120.8(5) . . ?
C26 C25 C24 119.1(5) . . ?
C26 C25 H25 117(4) . . ?
C24 C25 H25 124(4) . . ?
C25 C26 C27 122.6(5) . . ?
C25 C26 N3 119.0(5) . . ?
C27 C26 N3 118.4(5) . . ?
C26 C27 C28 117.0(5) . . ?
C26 C27 H27 120(4) . . ?
C28 C27 H27 123(4) . . ?
C29 C28 C27 122.8(5) . . ?
C29 C28 N4 119.1(5) . . ?
C27 C28 N4 118.1(5) . . ?
C28 C29 C24 119.0(5) . . ?
C28 C29 H29 121(3) . . ?
C24 C29 H29 120(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
_geom_hbond_publ_flag
C2 H2 F3 0.95 2.41 3.343(6) 169.0 1_545 yes
C12 H12 F1 0.95 2.51 3.286(6) 139.0 4_656 yes
C14 H14A O4 0.98 2.59 3.225(7) 122.4 2_565 yes
C14 H14B O3 0.98 2.61 3.564(7) 164.8 2_575 yes
C14 H14C O3 0.98 2.59 3.497(7) 153.5 4_646 yes

_refine_diff_density_max         0.589
_refine_diff_density_min         -1.041
_refine_diff_density_rms         0.088

####################################################################### 
# 
# 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_eb643_a
_database_code_depnum_ccdc_archive 'CCDC 1820040'
_audit_update_record             
;
2018-03-16 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1

_chemical_name_systematic        ?
_chemical_name_common            
;
Co-crystal between 4-[4-(N,N-dimethylamino) phenylethynyl] pyridine 
and 1-(3,5-dinitrophenylethynyl)-2,3,5,6-tetrafluoro-4-iodobenzene
;

_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H3 F4 I N2 O4, C15 H14 N2'
_chemical_formula_sum            'C29 H17 F4 I N4 O4'
_chemical_formula_weight         688.36

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'
F F 0.0171 0.0103 '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/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                   24.1533(13)
_cell_length_b                   6.8223(4)
_cell_length_c                   16.8260(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.6000(10)
_cell_angle_gamma                90
_cell_volume                     2670.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8214
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.21

_exptl_crystal_description       'cut rod'
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.271
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS V2014 (Bruker, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3660


_diffrn_reflns_number            31716
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.751
_diffrn_reflns_theta_max         27.409
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6030
_reflns_number_gt                4992
_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       'SMART, Bruker, 2014'
_computing_cell_refinement       'SMART, Bruker, 2014'
_computing_data_reduction        'SAINT, Bruker, 2014'
_computing_structure_solution    'SHELXT 2014/6 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_molecular_graphics    'XSeed (Barbour, 2001)'
_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)+(0.0351P)²+2.2799P] 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         6030
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0730
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.002
_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 0.49549(2) 0.64218(2) 0.33266(2) 0.02014(6) Uani 1 1 d . . . . .
F1 F 0.72295(6) 0.5828(3) 0.47386(10) 0.0304(4) Uani 1 1 d . . . . .
O1 O 0.83870(9) 0.6287(3) 0.99620(13) 0.0326(5) Uani 1 1 d . . . . .
N1 N 0.40632(9) 0.5958(3) 0.18826(13) 0.0210(5) Uani 1 1 d . . . . .
C1 C 0.31205(11) 0.5569(4) 0.09697(16) 0.0213(5) Uani 1 1 d . . . . .
H1 H 0.272895 0.523182 0.090204 0.026 Uiso 1 1 calc R U . . .
F2 F 0.62930(7) 0.5774(2) 0.34662(9) 0.0280(4) Uani 1 1 d . . . . .
O2 O 0.93160(9) 0.6055(3) 1.02250(12) 0.0364(5) Uani 1 1 d . . . . .
N2 N 0.12176(9) 0.6603(4) -0.44856(13) 0.0235(5) Uani 1 1 d . . . . .
C2 C 0.35057(11) 0.5519(4) 0.17460(16) 0.0221(6) Uani 1 1 d . . . . .
H2 H 0.336730 0.515577 0.220292 0.026 Uiso 1 1 calc R U . . .
F3 F 0.51594(6) 0.7463(3) 0.52588(9) 0.0291(4) Uani 1 1 d . . . . .
O3 O 1.02185(9) 0.6386(5) 0.79953(15) 0.0560(8) Uani 1 1 d . . . . .
N3 N 0.88346(10) 0.6185(3) 0.97471(14) 0.0255(5) Uani 1 1 d . . . . .
C3 C 0.42500(11) 0.6434(4) 0.12234(16) 0.0200(5) Uani 1 1 d . . . . .
H3 H 0.464706 0.671302 0.130898 0.024 Uiso 1 1 calc R U . . .
F4 F 0.61020(7) 0.7436(3) 0.65411(9) 0.0291(4) Uani 1 1 d . . . . .
O4 O 0.97087(10) 0.6054(4) 0.67477(14) 0.0505(7) Uani 1 1 d . . . . .
N4 N 0.97597(10) 0.6239(3) 0.74831(15) 0.0260(5) Uani 1 1 d . . . . .
C4 C 0.38961(11) 0.6539(4) 0.04278(16) 0.0183(5) Uani 1 1 d . . . . .
H4 H 0.404791 0.689161 -0.001780 0.022 Uiso 1 1 calc R U . . .
C5 C 0.33090(11) 0.6116(3) 0.02888(15) 0.0169(5) Uani 1 1 d . . . . .
C6 C 0.29209(11) 0.6231(4) -0.05185(16) 0.0205(5) Uani 1 1 d . . . . .
C7 C 0.25951(11) 0.6290(4) -0.11976(16) 0.0199(5) Uani 1 1 d . . . . .
C8 C 0.22354(11) 0.6328(4) -0.20243(15) 0.0178(5) Uani 1 1 d . . . . .
C9 C 0.24841(11) 0.6315(4) -0.26849(16) 0.0194(5) Uani 1 1 d . . . . .
H9 H 0.289088 0.627374 -0.257482 0.023 Uiso 1 1 calc R U . . .
C10 C 0.21531(11) 0.6361(4) -0.34920(16) 0.0196(5) Uani 1 1 d . . . . .
H10 H 0.233453 0.633933 -0.392774 0.024 Uiso 1 1 calc R U . . .
C11 C 0.15451(11) 0.6440(4) -0.36794(15) 0.0176(5) Uani 1 1 d . . . . .
C12 C 0.12930(11) 0.6382(4) -0.30187(15) 0.0173(5) Uani 1 1 d . . . . .
H12 H 0.088624 0.637725 -0.312551 0.021 Uiso 1 1 calc R U . . .
C13 C 0.16348(11) 0.6332(4) -0.22095(16) 0.0178(5) Uani 1 1 d . . . . .
H13 H 0.145616 0.629972 -0.177089 0.021 Uiso 1 1 calc R U . . .
C14 C 0.14846(12) 0.6433(4) -0.51615(16) 0.0240(6) Uani 1 1 d . . . . .
H14A H 0.178531 0.743021 -0.509968 0.036 Uiso 1 1 calc R U . . .
H14B H 0.119334 0.662798 -0.568728 0.036 Uiso 1 1 calc R U . . .
H14C H 0.165498 0.512697 -0.515294 0.036 Uiso 1 1 calc R U . . .
C15 C 0.06009(11) 0.6297(4) -0.46791(17) 0.0231(6) Uani 1 1 d . . . . .
H15A H 0.052262 0.501504 -0.446954 0.035 Uiso 1 1 calc R U . . .
H15B H 0.043675 0.633990 -0.527855 0.035 Uiso 1 1 calc R U . . .
H15C H 0.042716 0.732823 -0.441979 0.035 Uiso 1 1 calc R U . . .
C16 C 0.67162(11) 0.6196(4) 0.48766(17) 0.0208(6) Uani 1 1 d . . . . .
C17 C 0.62313(11) 0.6192(4) 0.42196(16) 0.0188(5) Uani 1 1 d . . . . .
C18 C 0.56928(10) 0.6578(4) 0.43264(16) 0.0179(5) Uani 1 1 d . . . . .
C19 C 0.56684(11) 0.7001(4) 0.51216(16) 0.0198(5) Uani 1 1 d . . . . .
C20 C 0.61519(11) 0.6997(4) 0.57843(16) 0.0199(5) Uani 1 1 d . . . . .
C21 C 0.66919(11) 0.6564(4) 0.56804(16) 0.0190(5) Uani 1 1 d . . . . .
C22 C 0.72059(11) 0.6529(4) 0.63473(17) 0.0221(6) Uani 1 1 d . . . . .
C23 C 0.76537(11) 0.6490(4) 0.68626(17) 0.0224(6) Uani 1 1 d . . . . .
C24 C 0.82056(11) 0.6421(4) 0.74593(16) 0.0199(5) Uani 1 1 d . . . . .
C25 C 0.82499(11) 0.6379(4) 0.83018(17) 0.0208(5) Uani 1 1 d . . . . .
H25 H 0.791514 0.643697 0.849513 0.025 Uiso 1 1 calc R U . . .
C26 C 0.87908(11) 0.6251(4) 0.88539(16) 0.0200(5) Uani 1 1 d . . . . .
C27 C 0.92928(11) 0.6187(4) 0.86088(16) 0.0207(5) Uani 1 1 d . . . . .
H27 H 0.965917 0.608405 0.899606 0.025 Uiso 1 1 calc R U . . .
C28 C 0.92323(11) 0.6280(4) 0.77693(17) 0.0199(5) Uani 1 1 d . . . . .
C29 C 0.87060(11) 0.6387(4) 0.71895(16) 0.0199(5) Uani 1 1 d . . . . .
H29 H 0.868351 0.643661 0.661743 0.024 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 C18 2.099(2) . ?
F1 C16 1.345(3) . ?
O1 N3 1.231(3) . ?
N1 C2 1.338(3) . ?
N1 C3 1.345(3) . ?
C1 C2 1.385(4) . ?
C1 C5 1.393(4) . ?
C1 H1 0.9500 . ?
F2 C17 1.346(3) . ?
O2 N3 1.226(3) . ?
N2 C11 1.379(3) . ?
N2 C15 1.452(3) . ?
N2 C14 1.455(3) . ?
C2 H2 0.9500 . ?
F3 C19 1.348(3) . ?
O3 N4 1.211(3) . ?
N3 C26 1.479(3) . ?
C3 C4 1.383(4) . ?
C3 H3 0.9500 . ?
F4 C20 1.345(3) . ?
O4 N4 1.217(3) . ?
N4 C28 1.478(3) . ?
C4 C5 1.404(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.430(3) . ?
C6 C7 1.201(4) . ?
C7 C8 1.428(4) . ?
C8 C9 1.398(4) . ?
C8 C13 1.399(4) . ?
C9 C10 1.379(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.418(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.404(4) . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.378(4) . ?
C16 C21 1.392(4) . ?
C17 C18 1.385(4) . ?
C18 C19 1.385(4) . ?
C19 C20 1.381(3) . ?
C20 C21 1.394(4) . ?
C21 C22 1.432(3) . ?
C22 C23 1.191(4) . ?
C23 C24 1.438(4) . ?
C24 C25 1.393(4) . ?
C24 C29 1.401(4) . ?
C25 C26 1.387(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.383(4) . ?
C27 C28 1.382(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.381(4) . ?
C29 H29 0.9500 . ?

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 117.3(2) . . ?
C2 C1 C5 119.8(2) . . ?
C2 C1 H1 120.1 . . ?
C5 C1 H1 120.1 . . ?
C11 N2 C15 119.5(2) . . ?
C11 N2 C14 120.3(2) . . ?
C15 N2 C14 117.2(2) . . ?
N1 C2 C1 123.1(3) . . ?
N1 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
O2 N3 O1 124.4(2) . . ?
O2 N3 C26 117.7(2) . . ?
O1 N3 C26 117.9(2) . . ?
N1 C3 C4 123.6(2) . . ?
N1 C3 H3 118.2 . . ?
C4 C3 H3 118.2 . . ?
O3 N4 O4 123.7(3) . . ?
O3 N4 C28 118.0(2) . . ?
O4 N4 C28 118.2(2) . . ?
C3 C4 C5 119.0(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C1 C5 C4 117.2(2) . . ?
C1 C5 C6 121.4(2) . . ?
C4 C5 C6 121.4(2) . . ?
C7 C6 C5 178.8(3) . . ?
C6 C7 C8 176.6(3) . . ?
C9 C8 C13 117.7(2) . . ?
C9 C8 C7 119.7(2) . . ?
C13 C8 C7 122.6(2) . . ?
C10 C9 C8 121.6(2) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 120.8(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
N2 C11 C12 121.7(2) . . ?
N2 C11 C10 120.5(2) . . ?
C12 C11 C10 117.8(2) . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C8 121.7(2) . . ?
C12 C13 H13 119.2 . . ?
C8 C13 H13 119.2 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
F1 C16 C17 119.0(2) . . ?
F1 C16 C21 118.9(2) . . ?
C17 C16 C21 122.1(2) . . ?
F2 C17 C16 118.1(2) . . ?
F2 C17 C18 120.5(2) . . ?
C16 C17 C18 121.4(2) . . ?
C17 C18 C19 116.8(2) . . ?
C17 C18 I1 120.73(19) . . ?
C19 C18 I1 122.48(18) . . ?
F3 C19 C20 118.3(2) . . ?
F3 C19 C18 119.5(2) . . ?
C20 C19 C18 122.2(2) . . ?
F4 C20 C19 119.5(2) . . ?
F4 C20 C21 119.4(2) . . ?
C19 C20 C21 121.1(2) . . ?
C16 C21 C20 116.5(2) . . ?
C16 C21 C22 120.3(2) . . ?
C20 C21 C22 123.3(3) . . ?
C23 C22 C21 175.5(3) . . ?
C22 C23 C24 177.7(3) . . ?
C25 C24 C29 119.5(2) . . ?
C25 C24 C23 121.0(2) . . ?
C29 C24 C23 119.5(2) . . ?
C26 C25 C24 118.9(2) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C27 C26 C25 123.1(3) . . ?
C27 C26 N3 118.3(2) . . ?
C25 C26 N3 118.7(2) . . ?
C28 C27 C26 116.3(2) . . ?
C28 C27 H27 121.8 . . ?
C26 C27 H27 121.8 . . ?
C29 C28 C27 123.3(2) . . ?
C29 C28 N4 118.8(2) . . ?
C27 C28 N4 117.9(2) . . ?
C28 C29 C24 118.9(2) . . ?
C28 C29 H29 120.6 . . ?
C24 C29 H29 120.6 . . ?

_refine_diff_density_max         0.900
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.092

####################################################################### 
# 
# 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_692_a
_database_code_depnum_ccdc_archive 'CCDC 1820042'
_audit_update_record             
;
2018-03-16 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1

_chemical_name_systematic        ?
_chemical_name_common            
;
Co-crystal between 2-[4-(N,N-dimethylamino) phenylethynyl] pyridine 
and 1-(3,5-dinitrophenylethynyl)-2,3,5,6-tetrafluoro-4-iodobenzene
;

_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H3 F4 I N2 O4, C15 H14 N2'
_chemical_formula_sum            'C29 H17 F4 I N4 O4'
_chemical_formula_weight         688.36

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'
F F 0.0171 0.0103 '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/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                   7.6541(10)
_cell_length_b                   13.8231(18)
_cell_length_c                   26.027(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.058(2)
_cell_angle_gamma                90
_cell_volume                     2753.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      24.34

_exptl_crystal_description       'cut rod'
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    1.233
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS V2014 (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3660

_diffrn_reflns_number            35822
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         0.782
_diffrn_reflns_theta_max         27.299
_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             6181
_reflns_number_gt                5161
_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       'SMART, Bruker, 2014'
_computing_cell_refinement       'SMART, Bruker, 2014'
_computing_data_reduction        'SAINT, Bruker, 2014'
_computing_structure_solution    'SHELXT 2014/6 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_molecular_graphics    'XSeed (Barbour, 2001)'
_computing_publication_material  'XSeed (Barbour, 2001)'

_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)+(0.0728P)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         6181
_refine_ls_number_parameters     382
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 0.76326(4) 0.06973(2) 0.24331(2) 0.06248(11) Uani 1 1 d . . . . .
F1 F 0.7340(4) 0.45862(18) 0.23478(10) 0.0757(7) Uani 1 1 d . . . . .
O1 O 0.1942(6) 0.6338(2) -0.04030(13) 0.0833(10) Uani 1 1 d . . . . .
N1 N 0.8213(5) -0.1197(2) 0.28743(14) 0.0562(8) Uani 1 1 d . . . . .
C1 C 0.7667(6) -0.2002(3) 0.26183(17) 0.0660(11) Uani 1 1 d . . . . .
H1 H 0.718411 -0.193134 0.228401 0.079 Uiso 1 1 calc R U . . .
F2 F 0.8188(4) 0.29078(19) 0.27855(11) 0.0731(8) Uani 1 1 d . . . . .
O2 O 0.1708(6) 0.7894(3) -0.03841(13) 0.0837(11) Uani 1 1 d . . . . .
N2 N 1.2414(7) 0.3802(3) 0.46168(16) 0.0821(12) Uani 1 1 d . . . . .
C2 C 0.7791(7) -0.2907(3) 0.28256(19) 0.0690(12) Uani 1 1 d . . . . .
H2 H 0.741253 -0.345456 0.263508 0.083 Uiso 1 1 calc R U . . .
F3 F 0.5798(5) 0.12499(19) 0.13615(12) 0.0825(8) Uani 1 1 d . . . . .
O3 O 0.2997(8) 0.9587(2) 0.11799(17) 0.1152(18) Uani 1 1 d . . . . .
N3 N 0.2146(6) 0.7115(3) -0.01914(14) 0.0633(9) Uani 1 1 d . . . . .
C3 C 0.8460(7) -0.3021(3) 0.3307(2) 0.0733(13) Uani 1 1 d . . . . .
H3 H 0.854140 -0.364760 0.345448 0.088 Uiso 1 1 calc R U . . .
F4 F 0.4909(4) 0.2929(2) 0.09377(11) 0.0745(8) Uani 1 1 d . . . . .
O4 O 0.4837(6) 0.8953(3) 0.17035(15) 0.0924(12) Uani 1 1 d . . . . .
N4 N 0.3870(6) 0.8912(3) 0.13331(16) 0.0706(11) Uani 1 1 d . . . . .
C4 C 0.9020(6) -0.2221(3) 0.35785(19) 0.0619(11) Uani 1 1 d . . . . .
H4 H 0.949084 -0.228662 0.391449 0.074 Uiso 1 1 calc R U . . .
C5 C 0.8877(5) -0.1318(3) 0.33491(16) 0.0515(9) Uani 1 1 d . . . . .
C6 C 0.9487(7) -0.0461(3) 0.3601(2) 0.0600(11) Uani 1 1 d . . . . .
C7 C 1.0033(6) 0.0254(4) 0.38021(19) 0.0585(11) Uani 1 1 d . . . . .
C8 C 1.0634(6) 0.1140(3) 0.40118(17) 0.0542(9) Uani 1 1 d . . . . .
C9 C 1.1338(6) 0.1211(3) 0.45103(18) 0.0593(10) Uani 1 1 d . . . . .
H9 H 1.144651 0.064231 0.471323 0.071 Uiso 1 1 calc R U . . .
C10 C 1.1873(6) 0.2081(3) 0.47102(18) 0.0642(11) Uani 1 1 d . . . . .
H10 H 1.229012 0.210247 0.505390 0.077 Uiso 1 1 calc R U . . .
C11 C 1.1822(6) 0.2928(3) 0.44273(19) 0.0617(11) Uani 1 1 d . . . . .
C12 C 1.1172(7) 0.2853(3) 0.39154(19) 0.0639(11) Uani 1 1 d . . . . .
H12 H 1.111023 0.341374 0.370481 0.077 Uiso 1 1 calc R U . . .
C13 C 1.0633(7) 0.1974(3) 0.37248(18) 0.0624(11) Uani 1 1 d . . . . .
H13 H 1.024068 0.194276 0.337880 0.075 Uiso 1 1 calc R U . . .
C14 C 1.2881(11) 0.3871(4) 0.5147(2) 0.102(2) Uani 1 1 d . . . . .
H14A H 1.185641 0.372949 0.536002 0.152 Uiso 1 1 calc R U . . .
H14B H 1.329695 0.452678 0.522154 0.152 Uiso 1 1 calc R U . . .
H14C H 1.380856 0.340426 0.522403 0.152 Uiso 1 1 calc R U . . .
C15 C 1.2028(11) 0.4690(4) 0.4335(3) 0.110(2) Uani 1 1 d . . . . .
H15A H 1.264663 0.468348 0.400599 0.165 Uiso 1 1 calc R U . . .
H15B H 1.241099 0.524922 0.453788 0.165 Uiso 1 1 calc R U . . .
H15C H 1.076738 0.473408 0.427361 0.165 Uiso 1 1 calc R U . . .
C16 C 0.6929(6) 0.3767(3) 0.21089(17) 0.0562(10) Uani 1 1 d . . . . .
C17 C 0.7381(7) 0.2894(3) 0.23175(15) 0.0564(10) Uani 1 1 d . . . . .
C18 C 0.7041(5) 0.2027(3) 0.20870(16) 0.0548(9) Uani 1 1 d . . . . .
C19 C 0.6196(6) 0.2065(3) 0.16152(17) 0.0580(10) Uani 1 1 d . . . . .
C20 C 0.5747(6) 0.2937(3) 0.13940(16) 0.0565(10) Uani 1 1 d . . . . .
C21 C 0.6072(5) 0.3805(3) 0.16302(16) 0.0539(10) Uani 1 1 d . . . . .
C22 C 0.5530(6) 0.4705(3) 0.14132(18) 0.0576(10) Uani 1 1 d . . . . .
C23 C 0.5013(6) 0.5412(3) 0.1224(2) 0.0576(11) Uani 1 1 d . . . . .
C24 C 0.4345(6) 0.6299(3) 0.10009(17) 0.0559(10) Uani 1 1 d . . . . .
C25 C 0.3575(6) 0.6280(3) 0.05190(16) 0.0560(10) Uani 1 1 d . . . . .
H25 H 0.348146 0.569079 0.033277 0.067 Uiso 1 1 calc R U . . .
C26 C 0.2944(6) 0.7135(3) 0.03143(15) 0.0511(9) Uani 1 1 d . . . . .
C27 C 0.2994(5) 0.8000(3) 0.05721(15) 0.0516(9) Uani 1 1 d . . . . .
H27 H 0.251151 0.857292 0.042893 0.062 Uiso 1 1 calc R U . . .
C28 C 0.3780(6) 0.7997(3) 0.10502(16) 0.0521(9) Uani 1 1 d . . . . .
C29 C 0.4460(6) 0.7169(3) 0.12732(17) 0.0556(10) Uani 1 1 d . . . . .
H29 H 0.499081 0.719174 0.160303 0.067 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 C18 2.096(4) . ?
F1 C16 1.329(5) . ?
O1 N3 1.217(5) . ?
N1 C5 1.346(5) . ?
N1 C1 1.362(5) . ?
C1 C2 1.366(6) . ?
C1 H1 0.9500 . ?
F2 C17 1.365(5) . ?
O2 N3 1.234(5) . ?
N2 C11 1.381(5) . ?
N2 C14 1.429(7) . ?
N2 C15 1.460(7) . ?
C2 C3 1.361(8) . ?
C2 H2 0.9500 . ?
F3 C19 1.341(5) . ?
O3 N4 1.214(6) . ?
N3 C26 1.451(6) . ?
C3 C4 1.381(6) . ?
C3 H3 0.9500 . ?
F4 C20 1.349(5) . ?
O4 N4 1.216(5) . ?
N4 C28 1.465(6) . ?
C4 C5 1.387(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.433(6) . ?
C6 C7 1.193(6) . ?
C7 C8 1.417(6) . ?
C8 C13 1.374(6) . ?
C8 C9 1.408(6) . ?
C9 C10 1.373(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.426(7) . ?
C12 C13 1.376(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.368(5) . ?
C16 C21 1.409(6) . ?
C17 C18 1.365(6) . ?
C18 C19 1.389(6) . ?
C19 C20 1.379(6) . ?
C20 C21 1.371(6) . ?
C21 C22 1.428(6) . ?
C22 C23 1.163(6) . ?
C23 C24 1.449(6) . ?
C24 C25 1.386(6) . ?
C24 C29 1.399(6) . ?
C25 C26 1.384(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.372(5) . ?
C27 C28 1.381(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.385(5) . ?
C29 H29 0.9500 . ?

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 117.6(4) . . ?
N1 C1 C2 122.3(4) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C11 N2 C14 119.0(4) . . ?
C11 N2 C15 119.4(5) . . ?
C14 N2 C15 118.6(4) . . ?
C3 C2 C1 119.7(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
O1 N3 O2 123.5(4) . . ?
O1 N3 C26 118.7(4) . . ?
O2 N3 C26 117.8(3) . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
O3 N4 O4 124.0(4) . . ?
O3 N4 C28 118.2(4) . . ?
O4 N4 C28 117.8(4) . . ?
C3 C4 C5 118.4(5) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 122.4(4) . . ?
N1 C5 C6 116.1(4) . . ?
C4 C5 C6 121.4(4) . . ?
C7 C6 C5 178.2(5) . . ?
C6 C7 C8 176.1(6) . . ?
C13 C8 C9 116.3(4) . . ?
C13 C8 C7 121.0(4) . . ?
C9 C8 C7 122.6(4) . . ?
C10 C9 C8 121.6(4) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 122.1(5) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
N2 C11 C10 122.8(5) . . ?
N2 C11 C12 120.7(4) . . ?
C10 C11 C12 116.5(4) . . ?
C13 C12 C11 120.3(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C8 C13 C12 123.0(5) . . ?
C8 C13 H13 118.5 . . ?
C12 C13 H13 118.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
F1 C16 C17 120.4(4) . . ?
F1 C16 C21 119.5(4) . . ?
C17 C16 C21 120.1(4) . . ?
F2 C17 C18 119.4(3) . . ?
F2 C17 C16 117.1(3) . . ?
C18 C17 C16 123.5(4) . . ?
C17 C18 C19 116.3(4) . . ?
C17 C18 I1 122.7(3) . . ?
C19 C18 I1 120.9(3) . . ?
F3 C19 C20 118.2(4) . . ?
F3 C19 C18 120.6(4) . . ?
C20 C19 C18 121.2(4) . . ?
F4 C20 C21 119.2(4) . . ?
F4 C20 C19 118.5(4) . . ?
C21 C20 C19 122.2(4) . . ?
C20 C21 C16 116.6(4) . . ?
C20 C21 C22 122.2(4) . . ?
C16 C21 C22 121.1(4) . . ?
C23 C22 C21 176.2(6) . . ?
C22 C23 C24 178.4(6) . . ?
C25 C24 C29 120.1(4) . . ?
C25 C24 C23 119.7(4) . . ?
C29 C24 C23 120.2(4) . . ?
C26 C25 C24 118.7(4) . . ?
C26 C25 H25 120.7 . . ?
C24 C25 H25 120.7 . . ?
C27 C26 C25 123.2(4) . . ?
C27 C26 N3 118.1(4) . . ?
C25 C26 N3 118.7(4) . . ?
C26 C27 C28 116.8(4) . . ?
C26 C27 H27 121.6 . . ?
C28 C27 H27 121.6 . . ?
C27 C28 C29 122.9(4) . . ?
C27 C28 N4 118.1(4) . . ?
C29 C28 N4 119.1(4) . . ?
C28 C29 C24 118.4(4) . . ?
C28 C29 H29 120.8 . . ?
C24 C29 H29 120.8 . . ?

_refine_diff_density_max         1.390
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.072

