# 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_4pca_14tfib
_database_code_depnum_ccdc_archive 'CCDC 1901942'
loop_
_audit_author_name
_audit_author_address
'Vinko Nemec'
;University of Zagreb
Croatia
;
_audit_update_record             
;
2019-03-08 deposited with the CCDC.	2019-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, C6 H5 N O'
_chemical_formula_sum            'C12 H5 F4 I2 N O'
_chemical_formula_weight         508.97

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      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                   4.2934(3)
_cell_length_b                   6.2651(4)
_cell_length_c                   13.2828(8)
_cell_angle_alpha                101.118(5)
_cell_angle_beta                 96.900(5)
_cell_angle_gamma                98.117(5)
_cell_volume                     343.05(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    150
_cell_measurement_reflns_used    2027
_cell_measurement_theta_min      4.8330
_cell_measurement_theta_max      38.3780

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.464
_exptl_crystal_F_000             234
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    4.623
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.30671
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            2287
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.747
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             1462
_reflns_number_gt                1426
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0666P)²+0.7961P] 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         1462
_refine_ls_number_parameters     112
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.136
_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
N1 N 0.619(5) 0.684(3) 0.8922(19) 0.039(5) Uani 0.5 1 d . . P A -1
C1 C 0.717(4) 0.486(3) 0.8663(15) 0.032(4) Uani 0.5 1 d . . P A -1
H1 H 0.6437 0.3997 0.8003 0.039 Uiso 0.5 1 calc R U P A -1
C2 C 0.920(4) 0.410(2) 0.9336(13) 0.029(3) Uani 0.5 1 d D . P A -1
H2 H 0.9745 0.2708 0.9138 0.035 Uiso 0.5 1 calc R U P A -1
C3 C 1.042(3) 0.538(2) 1.0298(9) 0.020(3) Uiso 0.5 1 d D . P A -1
C4 C 0.958(3) 0.7476(19) 1.0574(9) 0.026(2) Uani 0.5 1 d D . P A -1
H4 H 1.0308 0.8380 1.1226 0.031 Uiso 0.5 1 calc R U P A -1
C5 C 0.757(3) 0.815(2) 0.9815(10) 0.029(2) Uani 0.5 1 d . . P A -1
H5 H 0.7203 0.9593 0.9950 0.035 Uiso 0.5 1 calc R U P A -1
C6 C 1.262(4) 0.462(3) 1.1070(13) 0.028(5) Uiso 0.5 1 d D . P A -1
H6 H 1.3547 0.5619 1.1680 0.033 Uiso 0.5 1 calc R U P A -1
O1 O 1.324(4) 0.280(2) 1.0942(14) 0.024(4) Uiso 0.5 1 d D . P A -1
I1 I 0.35046(7) 0.83505(5) 0.71810(2) 0.02402(17) Uani 1 1 d . . . . .
F3 F -0.0136(9) 0.7515(5) 0.3077(3) 0.0300(8) Uani 1 1 d . . . . .
F2 F 0.2707(9) 0.6314(6) 0.4726(3) 0.0312(8) Uani 1 1 d . . . . .
C9 C -0.0088(13) 0.8773(9) 0.4029(4) 0.0209(10) Uani 1 1 d . . . . .
C7 C 0.1458(12) 0.9344(9) 0.5872(4) 0.0211(10) Uani 1 1 d . . . . .
C8 C 0.1360(13) 0.8137(9) 0.4887(5) 0.0218(10) 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
N1 C5 1.32(3) . ?
N1 C1 1.36(2) . ?
C1 C2 1.37(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.37(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.405(16) . ?
C3 C6 1.502(14) . ?
C4 C5 1.410(16) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 O1 1.193(16) . ?
C6 H6 0.9300 . ?
I1 C7 2.094(5) . ?
F3 C9 1.351(6) . ?
F2 C8 1.345(6) . ?
C9 C7 1.382(7) 2_576 ?
C9 C8 1.385(8) . ?
C7 C8 1.372(8) . ?
C7 C9 1.382(7) 2_576 ?

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 117.1(17) . . ?
N1 C1 C2 122.7(19) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 119.9(14) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 118.9(10) . . ?
C2 C3 C6 122.4(11) . . ?
C4 C3 C6 118.7(11) . . ?
C3 C4 C5 116.8(11) . . ?
C3 C4 H4 121.6 . . ?
C5 C4 H4 121.6 . . ?
N1 C5 C4 123.8(13) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
O1 C6 C3 123.4(16) . . ?
O1 C6 H6 118.3 . . ?
C3 C6 H6 118.3 . . ?
F3 C9 C7 119.8(5) . 2_576 ?
F3 C9 C8 118.7(5) . . ?
C7 C9 C8 121.5(5) 2_576 . ?
C8 C7 C9 117.3(5) . 2_576 ?
C8 C7 I1 121.7(4) . . ?
C9 C7 I1 121.0(4) 2_576 . ?
F2 C8 C7 120.7(5) . . ?
F2 C8 C9 118.1(5) . . ?
C7 C8 C9 121.2(5) . . ?

_refine_diff_density_max         1.179
_refine_diff_density_min         -2.195
_refine_diff_density_rms         0.196

####################################################################### 
# 
# 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_napht_2_14tfib
_database_code_depnum_ccdc_archive 'CCDC 1901946'
loop_
_audit_author_name
_audit_author_address
'Vinko Nemec'
;University of Zagreb
Croatia
;
_audit_update_record             
;
2019-03-08 deposited with the CCDC.	2019-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C11 H8 O2), C6 F4 I2'
_chemical_formula_sum            'C28 H16 F4 I2 O4'
_chemical_formula_weight         746.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.8371(8)
_cell_length_b                   12.5539(10)
_cell_length_c                   21.3222(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.397(7)
_cell_angle_gamma                90
_cell_volume                     2616.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    295
_cell_measurement_reflns_used    2984
_cell_measurement_theta_min      4.3730
_cell_measurement_theta_max      31.8880

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_F_000             1432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    2.465
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51299
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            16565
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.344
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5691
_reflns_number_gt                4067
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0321P)²+8.4475P] 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         5691
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1334
_refine_ls_wR_factor_gt          0.1220
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_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
I2 I 0.53081(5) 0.70527(4) 0.40803(2) 0.06061(17) Uani 1 1 d . . . . .
I1 I 0.03360(6) 0.71869(5) 0.61543(3) 0.06606(19) Uani 1 1 d . . . . .
F3 F 0.3610(5) 0.5223(3) 0.4680(2) 0.0732(13) Uani 1 1 d . . . . .
F2 F 0.3888(5) 0.8963(3) 0.4744(2) 0.0814(15) Uani 1 1 d . . . . .
F1 F 0.1977(5) 0.9013(3) 0.5528(2) 0.0812(15) Uani 1 1 d . . . . .
F4 F 0.1713(5) 0.5274(4) 0.5462(2) 0.0847(16) Uani 1 1 d . . . . .
O1 O -0.1946(6) 0.9242(4) 0.7619(3) 0.0710(15) Uani 1 1 d . . . . .
H1O H -0.1615 0.8789 0.7404 0.107 Uiso 1 1 calc R U . . .
O2 O -0.1383(6) 0.7356(5) 0.7272(3) 0.0714(16) Uani 1 1 d . . . . .
O4 O 0.6981(6) 0.6871(5) 0.2980(3) 0.0789(18) Uani 1 1 d . . . . .
C26 C 0.3802(6) 0.7106(6) 0.4688(3) 0.0454(15) Uani 1 1 d . . . . .
O3 O 0.7600(8) 0.4987(5) 0.2651(3) 0.095(2) Uani 1 1 d . . . . .
H3O H 0.7244 0.5440 0.2856 0.143 Uiso 1 1 calc R U . . .
C23 C 0.1782(7) 0.7149(6) 0.5520(3) 0.0476(16) Uani 1 1 d . . . . .
C27 C 0.3218(7) 0.6173(5) 0.4883(3) 0.0474(16) Uani 1 1 d . . . . .
C1 C -0.2965(7) 0.7671(5) 0.8000(3) 0.0453(15) Uani 1 1 d . . . . .
C2 C -0.2813(7) 0.8773(6) 0.7983(3) 0.0523(17) Uani 1 1 d . . . . .
C21 C 0.9416(7) 0.7016(5) 0.1818(3) 0.0438(15) Uani 1 1 d . . . . .
C24 C 0.2365(8) 0.8067(6) 0.5318(3) 0.0539(18) Uani 1 1 d . . . . .
C25 C 0.3351(8) 0.8038(6) 0.4917(3) 0.0534(18) Uani 1 1 d . . . . .
C10 C -0.3904(7) 0.7205(6) 0.8408(3) 0.0495(16) Uani 1 1 d . . . . .
C4 C -0.4429(8) 0.9020(6) 0.8728(4) 0.061(2) Uani 1 1 d . . . . .
H4 H -0.4910 0.9469 0.8971 0.074 Uiso 1 1 calc R U . . .
C20 C 0.9585(8) 0.8142(6) 0.1743(4) 0.062(2) Uani 1 1 d . . . . .
H20 H 0.9089 0.8611 0.1967 0.074 Uiso 1 1 calc R U . . .
C28 C 0.2234(7) 0.6201(5) 0.5288(3) 0.0506(17) Uani 1 1 d . . . . .
C12 C 0.8517(8) 0.6566(6) 0.2232(3) 0.0521(17) Uani 1 1 d . . . . .
C11 C -0.2188(8) 0.7020(6) 0.7615(3) 0.0593(19) Uani 1 1 d . . . . .
H11 H -0.2312 0.6286 0.7631 0.071 Uiso 1 1 calc R U . . .
C3 C -0.3556(8) 0.9453(6) 0.8337(4) 0.064(2) Uani 1 1 d . . . . .
H3A H -0.3461 1.0188 0.8308 0.077 Uiso 1 1 calc R U . . .
C22 C 0.7760(8) 0.7194(7) 0.2624(4) 0.064(2) Uani 1 1 d . . . . .
H22 H 0.7877 0.7928 0.2606 0.076 Uiso 1 1 calc R U . . .
C17 C 1.1092(9) 0.6761(8) 0.1057(4) 0.071(2) Uani 1 1 d . . . . .
H17 H 1.1598 0.6309 0.0826 0.086 Uiso 1 1 calc R U . . .
C16 C 1.0180(8) 0.6331(6) 0.1468(3) 0.0588(19) Uani 1 1 d . . . . .
C5 C -0.4613(7) 0.7911(6) 0.8768(3) 0.0522(17) Uani 1 1 d . . . . .
C19 C 1.0445(8) 0.8529(7) 0.1354(4) 0.069(2) Uani 1 1 d . . . . .
H19 H 1.0542 0.9262 0.1312 0.083 Uiso 1 1 calc R U . . .
C9 C -0.4123(9) 0.6121(7) 0.8460(4) 0.070(2) Uani 1 1 d . . . . .
H9 H -0.3665 0.5642 0.8225 0.084 Uiso 1 1 calc R U . . .
C6 C -0.5524(9) 0.7494(7) 0.9165(4) 0.069(2) Uani 1 1 d . . . . .
H6 H -0.5994 0.7956 0.9406 0.083 Uiso 1 1 calc R U . . .
C13 C 0.8438(9) 0.5465(6) 0.2275(4) 0.063(2) Uani 1 1 d . . . . .
C15 C 1.0029(9) 0.5238(7) 0.1530(4) 0.073(2) Uani 1 1 d . . . . .
H15 H 1.0535 0.4790 0.1298 0.088 Uiso 1 1 calc R U . . .
C18 C 1.1212(9) 0.7829(9) 0.1005(4) 0.076(3) Uani 1 1 d . . . . .
H18 H 1.1805 0.8110 0.0737 0.092 Uiso 1 1 calc R U . . .
C7 C -0.5734(10) 0.6429(8) 0.9206(4) 0.088(3) Uani 1 1 d . . . . .
H7 H -0.6354 0.6163 0.9465 0.105 Uiso 1 1 calc R U . . .
C14 C 0.9170(10) 0.4793(7) 0.1917(4) 0.081(3) Uani 1 1 d . . . . .
H14 H 0.9077 0.4057 0.1941 0.097 Uiso 1 1 calc R U . . .
C8 C -0.5027(11) 0.5758(7) 0.8863(5) 0.092(3) Uani 1 1 d . . . . .
H8 H -0.5155 0.5028 0.8900 0.111 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
I2 C26 2.076(6) . ?
I1 C23 2.070(6) . ?
F3 C27 1.342(7) . ?
F2 C25 1.345(8) . ?
F1 C24 1.339(8) . ?
F4 C28 1.340(8) . ?
O1 C2 1.351(8) . ?
O1 H1O 0.8200 . ?
O2 C11 1.213(9) . ?
O4 C22 1.207(9) . ?
C26 C25 1.361(9) . ?
C26 C27 1.388(9) . ?
O3 C13 1.353(9) . ?
O3 H3O 0.8200 . ?
C23 C24 1.378(9) . ?
C23 C28 1.381(9) . ?
C27 C28 1.367(9) . ?
C1 C2 1.392(10) . ?
C1 C11 1.437(9) . ?
C1 C10 1.460(9) . ?
C2 C3 1.399(10) . ?
C21 C16 1.409(9) . ?
C21 C12 1.433(9) . ?
C21 C20 1.435(9) . ?
C24 C25 1.363(9) . ?
C10 C9 1.383(10) . ?
C10 C5 1.407(9) . ?
C4 C3 1.374(10) . ?
C4 C5 1.407(10) . ?
C4 H4 0.9300 . ?
C20 C19 1.341(10) . ?
C20 H20 0.9300 . ?
C12 C13 1.388(10) . ?
C12 C22 1.420(10) . ?
C11 H11 0.9300 . ?
C3 H3A 0.9300 . ?
C22 H22 0.9300 . ?
C17 C18 1.353(13) . ?
C17 C16 1.428(10) . ?
C17 H17 0.9300 . ?
C16 C15 1.388(11) . ?
C5 C6 1.402(10) . ?
C19 C18 1.420(12) . ?
C19 H19 0.9300 . ?
C9 C8 1.380(11) . ?
C9 H9 0.9300 . ?
C6 C7 1.356(12) . ?
C6 H6 0.9300 . ?
C13 C14 1.390(11) . ?
C15 C14 1.365(11) . ?
C15 H15 0.9300 . ?
C18 H18 0.9300 . ?
C7 C8 1.358(13) . ?
C7 H7 0.9300 . ?
C14 H14 0.9300 . ?
C8 H8 0.9300 . ?

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 O1 H1O 109.5 . . ?
C25 C26 C27 117.1(6) . . ?
C25 C26 I2 122.4(5) . . ?
C27 C26 I2 120.6(5) . . ?
C13 O3 H3O 109.5 . . ?
C24 C23 C28 116.6(6) . . ?
C24 C23 I1 121.7(5) . . ?
C28 C23 I1 121.7(5) . . ?
F3 C27 C28 118.4(6) . . ?
F3 C27 C26 120.6(6) . . ?
C28 C27 C26 120.9(6) . . ?
C2 C1 C11 119.0(6) . . ?
C2 C1 C10 119.4(6) . . ?
C11 C1 C10 121.6(7) . . ?
O1 C2 C1 121.7(6) . . ?
O1 C2 C3 116.4(7) . . ?
C1 C2 C3 121.9(6) . . ?
C16 C21 C12 119.2(6) . . ?
C16 C21 C20 117.8(6) . . ?
C12 C21 C20 123.0(6) . . ?
F1 C24 C25 118.9(6) . . ?
F1 C24 C23 119.5(6) . . ?
C25 C24 C23 121.6(6) . . ?
F2 C25 C26 119.4(6) . . ?
F2 C25 C24 118.5(6) . . ?
C26 C25 C24 122.1(6) . . ?
C9 C10 C5 119.0(6) . . ?
C9 C10 C1 123.8(6) . . ?
C5 C10 C1 117.2(6) . . ?
C3 C4 C5 121.4(7) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C19 C20 C21 121.0(7) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
F4 C28 C27 118.2(6) . . ?
F4 C28 C23 120.1(6) . . ?
C27 C28 C23 121.7(6) . . ?
C13 C12 C22 118.5(7) . . ?
C13 C12 C21 118.4(6) . . ?
C22 C12 C21 122.9(7) . . ?
O2 C11 C1 124.8(7) . . ?
O2 C11 H11 117.6 . . ?
C1 C11 H11 117.6 . . ?
C4 C3 C2 119.1(7) . . ?
C4 C3 H3A 120.5 . . ?
C2 C3 H3A 120.5 . . ?
O4 C22 C12 126.5(8) . . ?
O4 C22 H22 116.7 . . ?
C12 C22 H22 116.7 . . ?
C18 C17 C16 119.4(8) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C15 C16 C21 118.9(7) . . ?
C15 C16 C17 120.8(8) . . ?
C21 C16 C17 120.2(8) . . ?
C6 C5 C10 118.9(7) . . ?
C6 C5 C4 120.1(7) . . ?
C10 C5 C4 121.0(6) . . ?
C20 C19 C18 120.6(8) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C8 C9 C10 119.4(8) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C7 C6 C5 121.2(8) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
O3 C13 C12 121.5(7) . . ?
O3 C13 C14 116.3(7) . . ?
C12 C13 C14 122.1(7) . . ?
C14 C15 C16 122.8(8) . . ?
C14 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C17 C18 C19 121.0(8) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C6 C7 C8 119.1(8) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C15 C14 C13 118.5(8) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C7 C8 C9 122.4(8) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?

_refine_diff_density_max         1.420
_refine_diff_density_min         -0.946
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_dmb_2_14tfib
_database_code_depnum_ccdc_archive 'CCDC 1901945'
loop_
_audit_author_name
_audit_author_address
'Vinko Nemec'
;University of Zagreb
Croatia
;
_audit_update_record             
;
2019-03-08 deposited with the CCDC.	2019-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, 2(C9 H10 O3)'
_chemical_formula_sum            'C24 H20 F4 I2 O6'
_chemical_formula_weight         734.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.2542(3)
_cell_length_b                   15.3640(5)
_cell_length_c                   10.5028(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.955(4)
_cell_angle_gamma                90
_cell_volume                     1274.04(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    295
_cell_measurement_reflns_used    4243
_cell_measurement_theta_min      4.4350
_cell_measurement_theta_max      32.1600

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_F_000             708
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    2.535
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.45699
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            13910
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.269
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2778
_reflns_number_gt                2318
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0354P)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         2778
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0644
_refine_ls_wR_factor_gt          0.0602
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.87232(2) 0.12238(2) 0.58979(2) 0.05423(9) Uani 1 1 d . . . . .
F2 F 0.20173(19) 0.08162(11) 0.38906(17) 0.0664(4) Uani 1 1 d . . . . .
F1 F 0.4852(2) 0.17383(9) 0.45767(17) 0.0638(4) Uani 1 1 d . . . . .
O2 O 0.68429(19) 0.46060(11) 0.56859(19) 0.0551(4) Uani 1 1 d . . . . .
O3 O 0.8250(2) 0.60838(10) 0.6325(2) 0.0522(4) Uani 1 1 d . . . . .
O1 O 1.1879(2) 0.23953(12) 0.6772(2) 0.0717(6) Uani 1 1 d . . . . .
C3 C 0.8558(3) 0.45806(15) 0.6183(2) 0.0395(5) Uani 1 1 d . . . . .
C4 C 0.9336(3) 0.54008(15) 0.6526(2) 0.0397(5) Uani 1 1 d . . . . .
C1 C 1.1299(3) 0.39120(15) 0.6844(3) 0.0434(5) Uani 1 1 d . . . . .
C10 C 0.6508(3) 0.04917(15) 0.5369(2) 0.0431(5) Uani 1 1 d . . . . .
C5 C 1.1076(3) 0.54620(16) 0.7031(2) 0.0443(5) Uani 1 1 d . . . . .
H5 H 1.1591 0.6000 0.7270 0.053 Uiso 1 1 calc R U . . .
C2 C 0.9531(3) 0.38489(14) 0.6349(3) 0.0423(5) Uani 1 1 d . . . . .
H2 H 0.9022 0.3307 0.6134 0.051 Uiso 1 1 calc R U . . .
C12 C 0.3475(3) 0.03940(16) 0.4438(2) 0.0476(5) Uani 1 1 d . . . . .
C11 C 0.4952(3) 0.08765(16) 0.4790(2) 0.0445(5) Uani 1 1 d . . . . .
C6 C 1.2045(3) 0.47135(16) 0.7177(2) 0.0467(6) Uani 1 1 d . . . . .
H6 H 1.3218 0.4753 0.7505 0.056 Uiso 1 1 calc R U . . .
C9 C 0.8944(4) 0.69337(17) 0.6634(3) 0.0581(7) Uani 1 1 d . . . . .
H9A H 0.9562 0.6963 0.7562 0.087 Uiso 1 1 calc R U . . .
H9B H 0.8045 0.7354 0.6440 0.087 Uiso 1 1 calc R U . . .
H9C H 0.9693 0.7057 0.6109 0.087 Uiso 1 1 calc R U . . .
C7 C 1.2351(3) 0.31397(18) 0.7020(3) 0.0558(7) Uani 1 1 d . . . . .
H7 H 1.3514 0.3225 0.7359 0.067 Uiso 1 1 calc R U . . .
C8 C 0.6004(3) 0.37968(16) 0.5262(4) 0.0644(9) Uani 1 1 d . . . . .
H8A H 0.6460 0.3533 0.4612 0.097 Uiso 1 1 calc R U . . .
H8B H 0.4814 0.3898 0.4876 0.097 Uiso 1 1 calc R U . . .
H8C H 0.6175 0.3415 0.6014 0.097 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 C10 2.079(2) . ?
F2 C12 1.340(3) . ?
F1 C11 1.341(3) . ?
O2 C3 1.359(2) . ?
O2 C8 1.430(3) . ?
O3 C4 1.356(3) . ?
O3 C9 1.425(3) . ?
O1 C7 1.212(3) . ?
C3 C2 1.363(3) . ?
C3 C4 1.412(3) . ?
C4 C5 1.382(3) . ?
C1 C6 1.376(3) . ?
C1 C2 1.402(3) . ?
C1 C7 1.450(3) . ?
C10 C12 1.375(3) 3_656 ?
C10 C11 1.383(3) . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C2 H2 0.9300 . ?
C12 C10 1.375(3) 3_656 ?
C12 C11 1.382(3) . ?
C6 H6 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 C8 116.77(18) . . ?
C4 O3 C9 118.0(2) . . ?
O2 C3 C2 125.6(2) . . ?
O2 C3 C4 114.69(19) . . ?
C2 C3 C4 119.73(19) . . ?
O3 C4 C5 125.0(2) . . ?
O3 C4 C3 114.82(19) . . ?
C5 C4 C3 120.2(2) . . ?
C6 C1 C2 119.8(2) . . ?
C6 C1 C7 119.5(2) . . ?
C2 C1 C7 120.7(2) . . ?
C12 C10 C11 117.1(2) 3_656 . ?
C12 C10 I1 121.72(18) 3_656 . ?
C11 C10 I1 121.18(18) . . ?
C4 C5 C6 119.2(2) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
F2 C12 C10 120.7(2) . 3_656 ?
F2 C12 C11 117.8(2) . . ?
C10 C12 C11 121.4(2) 3_656 . ?
F1 C11 C12 118.6(2) . . ?
F1 C11 C10 120.0(2) . . ?
C12 C11 C10 121.5(2) . . ?
C1 C6 C5 121.0(2) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C7 C1 127.0(2) . . ?
O1 C7 H7 116.5 . . ?
C1 C7 H7 116.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_van_14tfib
_database_code_depnum_ccdc_archive 'CCDC 1901944'
loop_
_audit_author_name
_audit_author_address
'Vinko Nemec'
;University of Zagreb
Croatia
;
_audit_update_record             
;
2019-03-08 deposited with the CCDC.	2019-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, C8 H8 O3'
_chemical_formula_sum            'C14 H8 F4 I2 O3'
_chemical_formula_weight         554.00

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   7.6135(5)
_cell_length_b                   28.680(2)
_cell_length_c                   7.4414(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.956(7)
_cell_angle_gamma                90
_cell_volume                     1605.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    295
_cell_measurement_reflns_used    3820
_cell_measurement_theta_min      3.9758
_cell_measurement_theta_max      36.9738

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.293
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_absorpt_coefficient_mu    3.970
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.58721
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            10189
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.404
_diffrn_reflns_theta_max         26.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3498
_reflns_number_gt                2647
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0401P)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         3498
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.1105
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_restrained_S_all      1.196
_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 0.85271(7) 0.38754(2) 0.88291(8) 0.05808(19) Uani 1 1 d . . . . .
I2 I 0.52342(8) 0.41855(2) 0.34902(8) 0.06063(19) Uani 1 1 d . . . . .
F3 F 0.3384(6) 0.41654(14) -0.0648(7) 0.0641(12) Uani 1 1 d . . . . .
F4 F 0.6846(6) 0.52146(15) 0.3281(6) 0.0668(13) Uani 1 1 d . . . . .
O3 O 0.4436(6) 0.17251(17) 0.0811(7) 0.0564(14) Uani 1 1 d . . . . .
H3 H 0.5176 0.1935 0.0964 0.085 Uiso 1 1 calc R U . . .
F2 F 0.8859(7) 0.47854(17) 0.6491(6) 0.0771(15) Uani 1 1 d . . . . .
F1 F 0.9999(7) 0.43539(16) 1.2647(6) 0.0743(15) Uani 1 1 d . . . . .
O2 O 0.4093(6) 0.26452(16) 0.0346(7) 0.0536(13) Uani 1 1 d . . . . .
O1 O -0.2618(7) 0.28531(19) -0.2247(8) 0.0610(15) Uani 1 1 d . . . . .
C2 C 0.0945(9) 0.2567(2) -0.0762(9) 0.0410(15) Uani 1 1 d . . . . .
H2 H 0.0800 0.2886 -0.0954 0.049 Uiso 1 1 calc R U . . .
C3 C 0.2578(9) 0.2393(2) -0.0095(9) 0.0383(15) Uani 1 1 d . . . . .
C9 C 0.9377(8) 0.4550(2) 0.9539(10) 0.0390(15) Uani 1 1 d . . . . .
C11 C 0.9426(10) 0.4884(3) 0.8240(9) 0.0463(17) Uani 1 1 d . . . . .
C12 C 0.5105(9) 0.4674(2) 0.1410(9) 0.0415(15) Uani 1 1 d . . . . .
C14 C 0.5899(9) 0.5104(3) 0.1666(10) 0.0472(17) Uani 1 1 d . . . . .
C4 C 0.2812(8) 0.1908(2) 0.0169(9) 0.0411(15) Uani 1 1 d . . . . .
C10 C 0.9998(9) 0.4668(3) 1.1297(10) 0.0470(17) Uani 1 1 d . . . . .
C1 C -0.0530(9) 0.2267(2) -0.1163(9) 0.0426(16) Uani 1 1 d . . . . .
C7 C -0.2265(10) 0.2451(3) -0.1881(11) 0.056(2) Uani 1 1 d . . . . .
H7 H -0.3198 0.2239 -0.2080 0.067 Uiso 1 1 calc R U . . .
C8 C 0.3914(10) 0.3144(2) 0.0269(11) 0.055(2) Uani 1 1 d . . . . .
H8A H 0.3397 0.3236 -0.0938 0.083 Uiso 1 1 calc R U . . .
H8B H 0.5065 0.3285 0.0577 0.083 Uiso 1 1 calc R U . . .
H8C H 0.3161 0.3243 0.1117 0.083 Uiso 1 1 calc R U . . .
C5 C 0.1389(10) 0.1613(3) -0.0194(10) 0.0515(19) Uani 1 1 d . . . . .
H5 H 0.1538 0.1295 0.0003 0.062 Uiso 1 1 calc R U . . .
C13 C 0.4199(8) 0.4573(2) -0.0296(10) 0.0429(16) Uani 1 1 d . . . . .
C6 C -0.0278(10) 0.1793(3) -0.0859(11) 0.0540(19) Uani 1 1 d . . . . .
H6 H -0.1244 0.1591 -0.1106 0.065 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 C9 2.081(6) . ?
I2 C12 2.078(7) . ?
F3 C13 1.331(7) . ?
F4 C14 1.340(8) . ?
O3 C4 1.360(7) . ?
O3 H3 0.8200 . ?
F2 C11 1.336(7) . ?
F1 C10 1.349(8) . ?
O2 C3 1.357(8) . ?
O2 C8 1.436(8) . ?
O1 C7 1.205(9) . ?
C2 C3 1.359(9) . ?
C2 C1 1.409(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.414(9) . ?
C9 C11 1.367(10) . ?
C9 C10 1.363(9) . ?
C11 C10 1.384(10) 3_767 ?
C12 C13 1.378(9) . ?
C12 C14 1.374(10) . ?
C14 C13 1.370(10) 3_665 ?
C4 C5 1.367(9) . ?
C10 C11 1.384(10) 3_767 ?
C1 C6 1.388(10) . ?
C1 C7 1.446(10) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C5 C6 1.388(10) . ?
C5 H5 0.9300 . ?
C13 C14 1.370(10) 3_665 ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O3 H3 109.5 . . ?
C3 O2 C8 116.6(5) . . ?
C3 C2 C1 120.4(6) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
O2 C3 C2 126.0(6) . . ?
O2 C3 C4 114.0(6) . . ?
C2 C3 C4 120.0(6) . . ?
C11 C9 C10 117.5(6) . . ?
C11 C9 I1 120.9(5) . . ?
C10 C9 I1 121.5(5) . . ?
F2 C11 C9 120.0(7) . . ?
F2 C11 C10 118.8(7) . 3_767 ?
C9 C11 C10 121.2(6) . 3_767 ?
C13 C12 C14 117.5(6) . . ?
C13 C12 I2 120.3(5) . . ?
C14 C12 I2 122.2(5) . . ?
F4 C14 C13 117.8(7) . 3_665 ?
F4 C14 C12 120.0(7) . . ?
C13 C14 C12 122.1(7) 3_665 . ?
O3 C4 C5 118.7(6) . . ?
O3 C4 C3 121.1(6) . . ?
C5 C4 C3 120.2(6) . . ?
F1 C10 C9 120.6(7) . . ?
F1 C10 C11 118.1(7) . 3_767 ?
C9 C10 C11 121.3(6) . 3_767 ?
C6 C1 C2 118.6(6) . . ?
C6 C1 C7 120.9(7) . . ?
C2 C1 C7 120.5(7) . . ?
O1 C7 C1 126.3(7) . . ?
O1 C7 H7 116.8 . . ?
C1 C7 H7 116.8 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C5 C6 119.6(7) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
F3 C13 C14 118.5(7) . 3_665 ?
F3 C13 C12 121.1(6) . . ?
C14 C13 C12 120.3(7) 3_665 . ?
C1 C6 C5 121.1(7) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?

_refine_diff_density_max         0.536
_refine_diff_density_min         -1.050
_refine_diff_density_rms         0.145

####################################################################### 
# 
# 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_dmab_2_14tfib
_database_code_depnum_ccdc_archive 'CCDC 1901943'
loop_
_audit_author_name
_audit_author_address
'Vinko Nemec'
;University of Zagreb
Croatia
;
_audit_update_record             
;
2019-03-08 deposited with the CCDC.	2019-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, 2(C9 H11 N O)'
_chemical_formula_sum            'C24 H22 F4 I2 N2 O2'
_chemical_formula_weight         700.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      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                   8.1668(5)
_cell_length_b                   8.4423(6)
_cell_length_c                   10.8612(5)
_cell_angle_alpha                100.288(5)
_cell_angle_beta                 105.696(5)
_cell_angle_gamma                110.297(6)
_cell_volume                     644.64(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    295
_cell_measurement_reflns_used    2371
_cell_measurement_theta_min      3.7384
_cell_measurement_theta_max      36.3640

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_F_000             338
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    2.491
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59223
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            6447
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.301
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2799
_reflns_number_gt                2327
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0312P)²+0.0112P] 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         2799
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0773
_refine_ls_wR_factor_gt          0.0723
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_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 0.74231(3) 0.74708(3) 0.16010(2) 0.06628(12) Uani 1 1 d . . . . .
F2 F 1.0510(4) 1.3406(3) 0.0336(3) 0.0971(8) Uani 1 1 d . . . . .
F1 F 0.8570(4) 1.1510(4) 0.1585(3) 0.0990(9) Uani 1 1 d . . . . .
O1 O 0.5564(5) 0.5116(4) 0.2914(3) 0.0920(9) Uani 1 1 d . . . . .
N1 N 0.1964(4) -0.2255(4) 0.4092(3) 0.0644(8) Uani 1 1 d . . . . .
C6 C 0.3723(5) 0.2258(5) 0.3884(4) 0.0597(9) Uani 1 1 d . . . . .
H6 H 0.3796 0.3357 0.4300 0.072 Uiso 1 1 calc R U . . .
C4 C 0.2756(4) -0.0851(5) 0.3682(3) 0.0521(8) Uani 1 1 d . . . . .
C1 C 0.4433(5) 0.2100(5) 0.2861(4) 0.0579(9) Uani 1 1 d . . . . .
C10 C 0.8958(5) 0.8996(5) 0.0653(3) 0.0530(8) Uani 1 1 d . . . . .
C5 C 0.2923(5) 0.0843(5) 0.4291(4) 0.0572(8) Uani 1 1 d . . . . .
H5 H 0.2478 0.0999 0.4986 0.069 Uiso 1 1 calc R U . . .
C7 C 0.5324(6) 0.3600(6) 0.2439(4) 0.0720(11) Uani 1 1 d . . . . .
H7 H 0.5752 0.3386 0.1742 0.086 Uiso 1 1 calc R U . . .
C9 C 0.1113(6) -0.2144(6) 0.5099(4) 0.0766(11) Uani 1 1 d . . . . .
H9A H 0.1852 -0.1030 0.5792 0.115 Uiso 1 1 calc R U . . .
H9B H 0.1053 -0.3094 0.5482 0.115 Uiso 1 1 calc R U . . .
H9C H -0.0128 -0.2234 0.4690 0.115 Uiso 1 1 calc R U . . .
C11 C 0.9276(5) 1.0730(5) 0.0804(4) 0.0593(9) Uani 1 1 d . . . . .
C3 C 0.3490(5) -0.0996(5) 0.2658(4) 0.0632(9) Uani 1 1 d . . . . .
H3 H 0.3431 -0.2088 0.2243 0.076 Uiso 1 1 calc R U . . .
C12 C 1.0281(5) 1.1716(5) 0.0162(4) 0.0611(9) Uani 1 1 d . . . . .
C2 C 0.4281(5) 0.0425(6) 0.2265(4) 0.0639(10) Uani 1 1 d . . . . .
H2 H 0.4738 0.0279 0.1575 0.077 Uiso 1 1 calc R U . . .
C8 C 0.1695(7) -0.4016(6) 0.3414(6) 0.0944(15) Uani 1 1 d . . . . .
H8A H 0.0674 -0.4477 0.2570 0.142 Uiso 1 1 calc R U . . .
H8B H 0.1415 -0.4775 0.3960 0.142 Uiso 1 1 calc R U . . .
H8C H 0.2815 -0.3963 0.3264 0.142 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 C10 2.084(3) . ?
F2 C12 1.344(4) . ?
F1 C11 1.348(4) . ?
O1 C7 1.216(5) . ?
N1 C4 1.355(4) . ?
N1 C8 1.447(5) . ?
N1 C9 1.452(5) . ?
C6 C5 1.361(5) . ?
C6 C1 1.393(5) . ?
C6 H6 0.9300 . ?
C4 C3 1.405(5) . ?
C4 C5 1.406(5) . ?
C1 C2 1.393(5) . ?
C1 C7 1.447(5) . ?
C10 C11 1.365(5) . ?
C10 C12 1.377(5) 2_775 ?
C5 H5 0.9300 . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 C12 1.377(5) . ?
C3 C2 1.354(5) . ?
C3 H3 0.9300 . ?
C12 C10 1.377(5) 2_775 ?
C2 H2 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C8 121.1(3) . . ?
C4 N1 C9 122.6(3) . . ?
C8 N1 C9 115.8(3) . . ?
C5 C6 C1 121.6(4) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
N1 C4 C3 122.1(3) . . ?
N1 C4 C5 121.2(3) . . ?
C3 C4 C5 116.7(3) . . ?
C6 C1 C2 117.1(3) . . ?
C6 C1 C7 122.2(4) . . ?
C2 C1 C7 120.7(4) . . ?
C11 C10 C12 116.6(3) . 2_775 ?
C11 C10 I1 122.7(2) . . ?
C12 C10 I1 120.7(3) 2_775 . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
O1 C7 C1 125.8(4) . . ?
O1 C7 H7 117.1 . . ?
C1 C7 H7 117.1 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
F1 C11 C10 119.7(3) . . ?
F1 C11 C12 118.3(3) . . ?
C10 C11 C12 122.0(3) . . ?
C2 C3 C4 121.2(4) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
F2 C12 C10 119.7(3) . 2_775 ?
F2 C12 C11 118.8(3) . . ?
C10 C12 C11 121.4(3) 2_775 . ?
C3 C2 C1 122.0(3) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         0.471
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.059

