# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1558860'
#Added by publCIF



_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-08-18 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  graphite
#Added by publCIF




_symmetry_space_group_name_hall  '-P 1'
# publcif _publ_body_element loop end
# start Validation Reply Form
_vrf_PLAT910_shelx               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          18 Note  
RESPONSE: This due to deleted (overflow) reflections at low angles which can be
 explained with high diffraction intensities.
;
# end Validation Reply Form 

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(2-(Adamantan-1-yliminomethyl)-6-methoxy-phenol)(1,2-diiodotetrafluorobenzene)
_chemical_name_common            
(2-(Adamantan-1-yliminomethyl)-6-methoxy-phenol)(1,2-diiodotetrafluorobenzene)
_chemical_melting_point          ?
_chemical_formula_moiety         (C18H23N1O2)(C6F4I2)
_chemical_formula_sum            'C24 H23 F4 I2 N O2'
_chemical_formula_weight         687.23

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                   10.1333(5)
_cell_length_b                   11.1817(6)
_cell_length_c                   13.0022(5)
_cell_angle_alpha                67.154(4)
_cell_angle_beta                 80.809(4)
_cell_angle_gamma                64.995(5)
_cell_volume                     1230.40(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3421
_cell_measurement_theta_min      4.0451
_cell_measurement_theta_max      40.7373

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.855
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.301
_exptl_crystal_size_min          0.097
_exptl_absorpt_coefficient_mu    2.607
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.57203
_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      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Kappa CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8036
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.051
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             5279
_reflns_number_gt                3265
_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)+(0.0298P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5279
_refine_ls_number_parameters     359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0594
_refine_ls_wR_factor_gt          0.0560
_refine_ls_goodness_of_fit_ref   0.813
_refine_ls_restrained_S_all      0.813
_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
F1 F 0.6617(2) 0.1793(2) 0.05054(17) 0.0738(6) Uani 1 1 d . . . . .
F3 F 0.4323(3) 0.6675(2) -0.29694(17) 0.0867(7) Uani 1 1 d . . . . .
F2 F 0.7196(3) 0.5106(3) -0.28533(18) 0.0884(7) Uani 1 1 d . . . . .
C106 C 0.5983(4) 0.3013(3) -0.0342(3) 0.0498(9) Uani 1 1 d . . . . .
C103 C 0.4840(4) 0.5459(4) -0.2087(3) 0.0554(9) Uani 1 1 d . . . . .
C105 C 0.6893(4) 0.3448(4) -0.1158(3) 0.0531(9) Uani 1 1 d . . . . .
C104 C 0.6313(4) 0.4675(4) -0.2055(3) 0.0587(10) Uani 1 1 d . . . . .
F4 F 0.8331(2) 0.2692(2) -0.11005(18) 0.0727(6) Uani 1 1 d . . . . .
H202 H -0.064(4) 0.669(3) -0.598(2) 0.049(10) Uiso 1 1 d . . . . .
H201 H -0.153(3) 0.608(3) -0.496(3) 0.045(9) Uiso 1 1 d . . . . .
H213 H -0.190(3) 0.920(3) -0.740(2) 0.038(8) Uiso 1 1 d . . . . .
H212 H -0.352(4) 1.004(4) -0.719(3) 0.062(11) Uiso 1 1 d . . . . .
H203 H -0.120(3) 0.513(3) -0.636(2) 0.046(9) Uiso 1 1 d . . . . .
H214 H -0.412(3) 0.747(4) -0.485(3) 0.057(10) Uiso 1 1 d . . . . .
H210 H -0.487(4) 0.799(4) -0.803(3) 0.067(11) Uiso 1 1 d . . . . .
H207 H -0.343(4) 0.541(4) -0.539(3) 0.056(10) Uiso 1 1 d . . . . .
H215 H -0.500(4) 0.900(5) -0.571(3) 0.085(13) Uiso 1 1 d . . . . .
H211 H -0.313(3) 0.899(3) -0.858(3) 0.051(9) Uiso 1 1 d . . . . .
H208 H -0.546(4) 0.743(4) -0.615(3) 0.059(10) Uiso 1 1 d . . . . .
H209 H -0.538(4) 0.928(4) -0.768(3) 0.059(11) Uiso 1 1 d . . . . .
H206 H -0.374(4) 0.556(4) -0.662(3) 0.084(13) Uiso 1 1 d . . . . .
H204 H -0.100(5) 0.697(4) -0.788(3) 0.080(13) Uiso 1 1 d . . . . .
H205 H -0.219(4) 0.658(4) -0.815(3) 0.081(13) Uiso 1 1 d . . . . .
I2 I 0.32527(3) 0.29448(3) 0.09149(2) 0.06413(9) Uani 1 1 d . . . . .
I1 I 0.17013(3) 0.63470(3) -0.14575(2) 0.06274(9) Uani 1 1 d . . . . .
N1 N -0.2373(3) 0.8653(3) -0.5169(2) 0.0429(6) Uani 1 1 d . . . . .
C7 C -0.2205(3) 0.9817(3) -0.5459(2) 0.0423(8) Uani 1 1 d . . . . .
H7 H -0.2298 1.0397 -0.6208 0.051 Uiso 1 1 calc R U . . .
C8 C -0.2720(3) 0.8152(3) -0.5947(2) 0.0406(7) Uani 1 1 d . . . . .
C1 C -0.1876(3) 1.0243(3) -0.4651(2) 0.0397(7) Uani 1 1 d . . . . .
C3 C -0.1387(3) 0.9821(3) -0.2748(2) 0.0419(8) Uani 1 1 d . . . . .
C102 C 0.3909(4) 0.5042(3) -0.1272(3) 0.0474(8) Uani 1 1 d . . . . .
C5 C -0.1455(3) 1.1966(3) -0.4231(3) 0.0511(9) Uani 1 1 d . . . . .
H5 H -0.1377 1.2833 -0.4463 0.061 Uiso 1 1 calc R U . . .
O1 O -0.1815(3) 0.8135(2) -0.31479(17) 0.0565(6) Uani 1 1 d . . . . .
H1 H -0.1996 0.7993 -0.3673 0.085 Uiso 1 1 calc R U . . .
C2 C -0.1701(3) 0.9372(3) -0.3518(3) 0.0413(7) Uani 1 1 d . . . . .
C6 C -0.1742(3) 1.1548(3) -0.4991(3) 0.0473(8) Uani 1 1 d . . . . .
H6 H -0.1852 1.2127 -0.5740 0.057 Uiso 1 1 calc R U . . .
C13 C -0.2778(5) 0.9091(4) -0.7178(3) 0.0513(9) Uani 1 1 d . . . . .
C101 C 0.4503(4) 0.3767(3) -0.0373(3) 0.0459(8) Uani 1 1 d . . . . .
O2 O -0.1219(3) 0.8888(2) -0.16671(17) 0.0551(6) Uani 1 1 d . . . . .
C14 C -0.4204(4) 0.8078(5) -0.5620(3) 0.0539(9) Uani 1 1 d . . . . .
C4 C -0.1274(3) 1.1104(4) -0.3105(3) 0.0478(8) Uani 1 1 d . . . . .
H4 H -0.1076 1.1399 -0.2592 0.057 Uiso 1 1 calc R U . . .
C9 C -0.1565(4) 0.6663(4) -0.5777(4) 0.0551(10) Uani 1 1 d . . . . .
C10 C -0.1929(4) 0.6036(4) -0.6497(3) 0.0595(10) Uani 1 1 d . . . . .
C12 C -0.3128(4) 0.8445(4) -0.7876(3) 0.0579(10) Uani 1 1 d . . . . .
C16 C -0.3401(5) 0.5961(4) -0.6153(4) 0.0669(11) Uani 1 1 d . . . . .
C15 C -0.4561(4) 0.7440(4) -0.6332(3) 0.0605(10) Uani 1 1 d . . . . .
C11 C -0.1963(5) 0.6980(5) -0.7716(3) 0.0663(11) Uani 1 1 d . . . . .
C17 C -0.4600(5) 0.8364(5) -0.7554(3) 0.0663(11) Uani 1 1 d . . . . .
C18 C -0.1132(5) 0.9361(5) -0.0831(3) 0.0797(13) Uani 1 1 d . . . . .
H18A H -0.0295 0.9593 -0.0958 0.120 Uiso 1 1 calc R U . . .
H18B H -0.1047 0.8628 -0.0113 0.120 Uiso 1 1 calc R U . . .
H18C H -0.1996 1.0185 -0.0851 0.120 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
F1 C106 1.344(3) . ?
F3 C103 1.349(4) . ?
F2 C104 1.338(4) . ?
C106 C105 1.371(5) . ?
C106 C101 1.373(5) . ?
C103 C104 1.372(5) . ?
C103 C102 1.378(5) . ?
C105 F4 1.337(4) . ?
C105 C104 1.372(5) . ?
I2 C101 2.089(3) . ?
I1 C102 2.081(3) . ?
N1 C7 1.284(4) . ?
N1 C8 1.477(4) . ?
C7 C1 1.442(4) . ?
C7 H7 0.9300 . ?
C8 C14 1.523(5) . ?
C8 C13 1.530(4) . ?
C8 C9 1.530(5) . ?
C1 C2 1.405(4) . ?
C1 C6 1.411(4) . ?
C3 O2 1.371(3) . ?
C3 C4 1.375(4) . ?
C3 C2 1.408(4) . ?
C102 C101 1.403(4) . ?
C5 C6 1.358(4) . ?
C5 C4 1.395(4) . ?
C5 H5 0.9300 . ?
O1 C2 1.326(4) . ?
O1 H1 0.8200 . ?
C6 H6 0.9300 . ?
C13 C12 1.517(5) . ?
C13 H213 0.93(3) . ?
C13 H212 1.01(4) . ?
O2 C18 1.410(4) . ?
C14 C15 1.528(5) . ?
C14 H214 0.96(3) . ?
C14 H215 0.98(4) . ?
C4 H4 0.9300 . ?
C9 C10 1.531(5) . ?
C9 H202 0.94(3) . ?
C9 H201 1.01(3) . ?
C10 C16 1.515(6) . ?
C10 C11 1.522(5) . ?
C10 H203 0.94(3) . ?
C12 C17 1.515(5) . ?
C12 C11 1.516(6) . ?
C12 H211 0.88(3) . ?
C16 C15 1.521(6) . ?
C16 H207 0.94(3) . ?
C16 H206 1.05(4) . ?
C15 C17 1.518(5) . ?
C15 H208 0.91(4) . ?
C11 H204 0.96(4) . ?
C11 H205 0.95(4) . ?
C17 H210 0.98(4) . ?
C17 H209 0.97(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
F1 C106 C105 116.3(3) . . ?
F1 C106 C101 121.0(3) . . ?
C105 C106 C101 122.7(3) . . ?
F3 C103 C104 116.8(3) . . ?
F3 C103 C102 120.5(3) . . ?
C104 C103 C102 122.7(3) . . ?
F4 C105 C106 121.2(3) . . ?
F4 C105 C104 119.6(3) . . ?
C106 C105 C104 119.2(3) . . ?
F2 C104 C105 119.5(4) . . ?
F2 C104 C103 121.6(3) . . ?
C105 C104 C103 118.9(3) . . ?
C7 N1 C8 124.5(3) . . ?
N1 C7 C1 121.5(3) . . ?
N1 C7 H7 119.3 . . ?
C1 C7 H7 119.3 . . ?
N1 C8 C14 107.4(3) . . ?
N1 C8 C13 114.7(3) . . ?
C14 C8 C13 108.5(3) . . ?
N1 C8 C9 107.3(2) . . ?
C14 C8 C9 109.2(3) . . ?
C13 C8 C9 109.6(3) . . ?
C2 C1 C6 119.4(3) . . ?
C2 C1 C7 120.4(3) . . ?
C6 C1 C7 120.2(3) . . ?
O2 C3 C4 125.5(3) . . ?
O2 C3 C2 114.5(3) . . ?
C4 C3 C2 120.1(3) . . ?
C103 C102 C101 118.2(3) . . ?
C103 C102 I1 117.7(2) . . ?
C101 C102 I1 124.1(2) . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C2 O1 H1 109.5 . . ?
O1 C2 C1 122.2(3) . . ?
O1 C2 C3 118.8(3) . . ?
C1 C2 C3 119.1(3) . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C12 C13 C8 109.0(3) . . ?
C12 C13 H213 111.0(18) . . ?
C8 C13 H213 110.8(17) . . ?
C12 C13 H212 116.7(18) . . ?
C8 C13 H212 103.0(19) . . ?
H213 C13 H212 106(3) . . ?
C106 C101 C102 118.3(3) . . ?
C106 C101 I2 118.3(2) . . ?
C102 C101 I2 123.4(3) . . ?
C3 O2 C18 117.4(3) . . ?
C8 C14 C15 109.8(3) . . ?
C8 C14 H214 106.0(19) . . ?
C15 C14 H214 109.7(19) . . ?
C8 C14 H215 114(2) . . ?
C15 C14 H215 108(2) . . ?
H214 C14 H215 110(3) . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C8 C9 C10 109.9(3) . . ?
C8 C9 H202 110.1(19) . . ?
C10 C9 H202 109(2) . . ?
C8 C9 H201 107.6(17) . . ?
C10 C9 H201 112.3(16) . . ?
H202 C9 H201 108(2) . . ?
C16 C10 C11 110.3(3) . . ?
C16 C10 C9 108.9(4) . . ?
C11 C10 C9 108.8(3) . . ?
C16 C10 H203 110.3(19) . . ?
C11 C10 H203 111.4(19) . . ?
C9 C10 H203 107.1(17) . . ?
C17 C12 C11 109.9(4) . . ?
C17 C12 C13 110.1(3) . . ?
C11 C12 C13 110.3(3) . . ?
C17 C12 H211 110(2) . . ?
C11 C12 H211 109(2) . . ?
C13 C12 H211 108(2) . . ?
C10 C16 C15 109.7(3) . . ?
C10 C16 H207 112(2) . . ?
C15 C16 H207 107(2) . . ?
C10 C16 H206 114(2) . . ?
C15 C16 H206 106(2) . . ?
H207 C16 H206 108(3) . . ?
C17 C15 C16 109.5(4) . . ?
C17 C15 C14 109.3(3) . . ?
C16 C15 C14 109.6(3) . . ?
C17 C15 H208 108(2) . . ?
C16 C15 H208 112(2) . . ?
C14 C15 H208 109(2) . . ?
C12 C11 C10 109.2(3) . . ?
C12 C11 H204 113(2) . . ?
C10 C11 H204 106(2) . . ?
C12 C11 H205 110(2) . . ?
C10 C11 H205 108(2) . . ?
H204 C11 H205 111(3) . . ?
C12 C17 C15 109.1(3) . . ?
C12 C17 H210 111(2) . . ?
C15 C17 H210 111(2) . . ?
C12 C17 H209 113(2) . . ?
C15 C17 H209 109(2) . . ?
H210 C17 H209 104(3) . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C106 C105 F4 -0.4(5) . . . . ?
C101 C106 C105 F4 179.7(3) . . . . ?
F1 C106 C105 C104 179.0(3) . . . . ?
C101 C106 C105 C104 -0.9(5) . . . . ?
F4 C105 C104 F2 -0.7(5) . . . . ?
C106 C105 C104 F2 179.9(3) . . . . ?
F4 C105 C104 C103 -178.2(3) . . . . ?
C106 C105 C104 C103 2.3(5) . . . . ?
F3 C103 C104 F2 0.8(5) . . . . ?
C102 C103 C104 F2 -179.6(3) . . . . ?
F3 C103 C104 C105 178.3(3) . . . . ?
C102 C103 C104 C105 -2.2(5) . . . . ?
C8 N1 C7 C1 179.6(3) . . . . ?
C7 N1 C8 C14 -116.9(3) . . . . ?
C7 N1 C8 C13 3.8(4) . . . . ?
C7 N1 C8 C9 125.8(3) . . . . ?
N1 C7 C1 C2 1.3(4) . . . . ?
N1 C7 C1 C6 -178.0(3) . . . . ?
F3 C103 C102 C101 180.0(3) . . . . ?
C104 C103 C102 C101 0.4(5) . . . . ?
F3 C103 C102 I1 0.1(4) . . . . ?
C104 C103 C102 I1 -179.4(3) . . . . ?
C6 C1 C2 O1 179.9(3) . . . . ?
C7 C1 C2 O1 0.6(5) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C7 C1 C2 C3 -179.7(3) . . . . ?
O2 C3 C2 O1 0.5(4) . . . . ?
C4 C3 C2 O1 -179.5(3) . . . . ?
O2 C3 C2 C1 -179.2(3) . . . . ?
C4 C3 C2 C1 0.8(4) . . . . ?
C4 C5 C6 C1 0.6(5) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
C7 C1 C6 C5 179.0(3) . . . . ?
N1 C8 C13 C12 179.4(3) . . . . ?
C14 C8 C13 C12 -60.5(4) . . . . ?
C9 C8 C13 C12 58.7(4) . . . . ?
F1 C106 C101 C102 179.2(3) . . . . ?
C105 C106 C101 C102 -0.8(5) . . . . ?
F1 C106 C101 I2 -1.3(4) . . . . ?
C105 C106 C101 I2 178.6(2) . . . . ?
C103 C102 C101 C106 1.0(4) . . . . ?
I1 C102 C101 C106 -179.1(2) . . . . ?
C103 C102 C101 I2 -178.4(2) . . . . ?
I1 C102 C101 I2 1.5(4) . . . . ?
C4 C3 O2 C18 9.7(5) . . . . ?
C2 C3 O2 C18 -170.3(3) . . . . ?
N1 C8 C14 C15 -175.0(3) . . . . ?
C13 C8 C14 C15 60.5(4) . . . . ?
C9 C8 C14 C15 -58.9(4) . . . . ?
O2 C3 C4 C5 179.4(3) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C6 C5 C4 C3 -0.1(5) . . . . ?
N1 C8 C9 C10 175.7(3) . . . . ?
C14 C8 C9 C10 59.5(4) . . . . ?
C13 C8 C9 C10 -59.2(4) . . . . ?
C8 C9 C10 C16 -60.3(4) . . . . ?
C8 C9 C10 C11 59.9(4) . . . . ?
C8 C13 C12 C17 61.1(4) . . . . ?
C8 C13 C12 C11 -60.3(4) . . . . ?
C11 C10 C16 C15 -58.6(5) . . . . ?
C9 C10 C16 C15 60.6(4) . . . . ?
C10 C16 C15 C17 59.3(4) . . . . ?
C10 C16 C15 C14 -60.6(4) . . . . ?
C8 C14 C15 C17 -60.4(4) . . . . ?
C8 C14 C15 C16 59.6(4) . . . . ?
C17 C12 C11 C10 -59.9(4) . . . . ?
C13 C12 C11 C10 61.7(4) . . . . ?
C16 C10 C11 C12 58.7(5) . . . . ?
C9 C10 C11 C12 -60.6(4) . . . . ?
C11 C12 C17 C15 61.0(5) . . . . ?
C13 C12 C17 C15 -60.6(5) . . . . ?
C16 C15 C17 C12 -60.4(4) . . . . ?
C14 C15 C17 C12 59.6(5) . . . . ?

_refine_diff_density_max         0.673
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.065


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 2-Propanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1558825'
#Added by publCIF



_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-08-18 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  graphite
#Added by publCIF




_symmetry_space_group_name_hall  '-P 1'
# publcif _publ_body_element loop end

# start Validation Reply Form
_vrf_PLAT910_shelx               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          17 Note  
RESPONSE: This due to deleted (overflow) reflections at low angles which can be
 explained with high diffraction intensities.
;
# end Validation Reply Form 
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(2-Methoxy-6-(naphthalen-1-yliminomethyl)-phenol)(1,4-diiodotetrafluorobenzene)
_chemical_name_common            
(2-Methoxy-6-(naphthalen-1-yliminomethyl)-phenol)(1,4-diiodotetrafluorobenzene)
_chemical_melting_point          ?
_chemical_formula_moiety         (C18H15NO2)(C6F4I2)
_chemical_formula_sum            'C24 H15 F4 I2 N O2'
_chemical_formula_weight         679.17

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'
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                   7.6601(3)
_cell_length_b                   12.7245(5)
_cell_length_c                   13.2834(6)
_cell_angle_alpha                98.744(3)
_cell_angle_beta                 103.077(4)
_cell_angle_gamma                107.441(4)
_cell_volume                     1169.04(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6465
_cell_measurement_theta_min      3.8615
_cell_measurement_theta_max      38.6689

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.929
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.601
_exptl_crystal_size_mid          0.532
_exptl_crystal_size_min          0.156
_exptl_absorpt_coefficient_mu    2.743
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.35557
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED (Oxford Diffraction, 2010), based on expressions derived by Clark
and Ried (1995)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Kappa CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14644
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.867
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             4964
_reflns_number_gt                2871
_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)+(0.0763P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4964
_refine_ls_number_parameters     303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1463
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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
C1 C 0.2726(6) 0.6449(3) 0.2190(3) 0.0517(10) Uani 1 1 d . . . . .
C2 C 0.4145(6) 0.7260(4) 0.3049(3) 0.0511(10) Uani 1 1 d . . . . .
C3 C 0.4569(7) 0.6988(4) 0.4032(4) 0.0600(12) Uani 1 1 d . . . . .
C4 C 0.3608(9) 0.5925(5) 0.4138(4) 0.0781(15) Uani 1 1 d . . . . .
H4 H 0.3903 0.5744 0.4793 0.094 Uiso 1 1 calc R U . . .
C5 C 0.2232(9) 0.5132(5) 0.3297(5) 0.0835(16) Uani 1 1 d . . . . .
H5 H 0.1600 0.4421 0.3387 0.100 Uiso 1 1 calc R U . . .
C6 C 0.1772(8) 0.5375(4) 0.2325(4) 0.0719(13) Uani 1 1 d . . . . .
H6 H 0.0833 0.4830 0.1755 0.086 Uiso 1 1 calc R U . . .
C7 C 0.2242(6) 0.6696(4) 0.1156(3) 0.0558(11) Uani 1 1 d . . . . .
H7 H 0.1304 0.6134 0.0600 0.067 Uiso 1 1 calc R U . . .
C8 C 0.2441(6) 0.7867(3) -0.0042(3) 0.0517(10) Uani 1 1 d . . . . .
C9 C 0.3886(6) 0.8395(3) -0.0483(3) 0.0500(10) Uani 1 1 d . . . . .
C10 C 0.5852(7) 0.8665(4) 0.0017(4) 0.0602(11) Uani 1 1 d . . . . .
H10 H 0.6239 0.8504 0.0673 0.072 Uiso 1 1 calc R U . . .
C11 C 0.7175(8) 0.9154(5) -0.0448(5) 0.0777(15) Uani 1 1 d . . . . .
H11 H 0.8462 0.9325 -0.0106 0.093 Uiso 1 1 calc R U . . .
C12 C 0.6651(10) 0.9406(5) -0.1426(5) 0.0887(18) Uani 1 1 d . . . . .
H12 H 0.7588 0.9746 -0.1730 0.106 Uiso 1 1 calc R U . . .
C13 C 0.4803(10) 0.9163(5) -0.1937(4) 0.0814(16) Uani 1 1 d . . . . .
H13 H 0.4480 0.9339 -0.2593 0.098 Uiso 1 1 calc R U . . .
C14 C 0.3329(7) 0.8643(4) -0.1499(3) 0.0624(12) Uani 1 1 d . . . . .
C15 C 0.1350(8) 0.8343(5) -0.2010(4) 0.0776(15) Uani 1 1 d . . . . .
H15 H 0.0968 0.8508 -0.2666 0.093 Uiso 1 1 calc R U . . .
C16 C -0.0013(8) 0.7815(5) -0.1561(4) 0.0753(14) Uani 1 1 d . . . . .
H16 H -0.1305 0.7598 -0.1920 0.090 Uiso 1 1 calc R U . . .
C17 C 0.0568(7) 0.7603(4) -0.0543(3) 0.0658(12) Uani 1 1 d . . . . .
H17 H -0.0346 0.7280 -0.0217 0.079 Uiso 1 1 calc R U . . .
C18 C 0.6364(11) 0.7634(7) 0.5866(4) 0.117(3) Uani 1 1 d . . . . .
H18A H 0.5241 0.7536 0.6101 0.175 Uiso 1 1 calc R U . . .
H18B H 0.7402 0.8272 0.6343 0.175 Uiso 1 1 calc R U . . .
H18C H 0.6698 0.6963 0.5858 0.175 Uiso 1 1 calc R U . . .
C101 C -0.0196(7) 0.2065(5) 0.6146(4) 0.0700(14) Uani 1 1 d . . . . .
C102 C 0.0672(7) 0.2195(5) 0.7192(5) 0.0706(14) Uani 1 1 d . . . . .
C103 C 0.1936(7) 0.3213(5) 0.7824(4) 0.0680(13) Uani 1 1 d . . . . .
C104 C 0.2419(7) 0.4163(4) 0.7434(4) 0.0637(12) Uani 1 1 d . . . . .
C105 C 0.1550(10) 0.4033(6) 0.6363(5) 0.0849(17) Uani 1 1 d . . . . .
C106 C 0.0295(9) 0.3009(6) 0.5747(4) 0.0808(16) Uani 1 1 d . . . . .
N1 N 0.3049(5) 0.7652(3) 0.0978(3) 0.0533(9) Uani 1 1 d . . . . .
O1 O 0.5116(5) 0.8301(3) 0.2976(3) 0.0686(10) Uani 1 1 d . . . . .
O2 O 0.5998(6) 0.7824(3) 0.4828(3) 0.0844(11) Uani 1 1 d . . . . .
F1 F 0.0284(6) 0.1294(4) 0.7629(3) 0.1214(15) Uani 1 1 d . . . . .
F2 F 0.2694(6) 0.3277(4) 0.8864(3) 0.1152(14) Uani 1 1 d . . . . .
F3 F 0.1937(7) 0.4934(4) 0.5949(3) 0.1400(17) Uani 1 1 d . . . . .
F4 F -0.0523(7) 0.2957(4) 0.4713(3) 0.1298(15) Uani 1 1 d . . . . .
I1 I -0.21703(5) 0.05374(4) 0.51948(4) 0.1066(2) Uani 1 1 d . . . . .
I2 I 0.41543(7) 0.57290(4) 0.83978(4) 0.1093(2) Uani 1 1 d . . . . .
H1 H 0.475(6) 0.824(4) 0.234(4) 0.056(14) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.399(6) . ?
C1 C6 1.404(7) . ?
C1 C7 1.447(6) . ?
C2 O1 1.341(6) . ?
C2 C3 1.394(6) . ?
C3 O2 1.373(6) . ?
C3 C4 1.378(7) . ?
C4 C5 1.365(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.273(5) . ?
C7 H7 0.9300 . ?
C8 C17 1.351(6) . ?
C8 C9 1.409(6) . ?
C8 N1 1.424(5) . ?
C9 C10 1.413(6) . ?
C9 C14 1.434(6) . ?
C10 C11 1.347(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.342(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.420(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.419(7) . ?
C15 C16 1.372(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.418(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O2 1.416(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C101 C102 1.359(7) . ?
C101 C106 1.370(8) . ?
C101 I1 2.071(5) . ?
C102 F1 1.347(6) . ?
C102 C103 1.368(8) . ?
C103 F2 1.351(6) . ?
C103 C104 1.369(7) . ?
C104 C105 1.388(8) . ?
C104 I2 2.060(5) . ?
C105 F3 1.330(7) . ?
C105 C106 1.365(9) . ?
C106 F4 1.357(6) . ?
O1 H1 0.81(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.8(4) . . ?
C2 C1 C7 120.9(4) . . ?
C6 C1 C7 119.3(4) . . ?
O1 C2 C3 117.9(4) . . ?
O1 C2 C1 122.9(4) . . ?
C3 C2 C1 119.1(4) . . ?
O2 C3 C4 124.9(4) . . ?
O2 C3 C2 115.4(4) . . ?
C4 C3 C2 119.6(5) . . ?
C5 C4 C3 121.2(5) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.6(5) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N1 C7 C1 122.6(4) . . ?
N1 C7 H7 118.7 . . ?
C1 C7 H7 118.7 . . ?
C17 C8 C9 122.0(4) . . ?
C17 C8 N1 121.2(4) . . ?
C9 C8 N1 116.8(4) . . ?
C8 C9 C10 123.1(4) . . ?
C8 C9 C14 118.4(4) . . ?
C10 C9 C14 118.5(4) . . ?
C11 C10 C9 120.7(5) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 121.2(6) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 120.5(5) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 121.5(5) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 124.2(5) . . ?
C15 C14 C9 118.3(4) . . ?
C13 C14 C9 117.6(5) . . ?
C16 C15 C14 121.6(4) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 119.3(5) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C8 C17 C16 120.5(5) . . ?
C8 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C102 C101 C106 116.3(5) . . ?
C102 C101 I1 122.5(4) . . ?
C106 C101 I1 121.2(4) . . ?
F1 C102 C101 119.3(5) . . ?
F1 C102 C103 118.4(5) . . ?
C101 C102 C103 122.3(5) . . ?
F2 C103 C102 118.5(5) . . ?
F2 C103 C104 119.7(5) . . ?
C102 C103 C104 121.8(5) . . ?
C103 C104 C105 116.2(5) . . ?
C103 C104 I2 122.2(4) . . ?
C105 C104 I2 121.4(4) . . ?
F3 C105 C106 120.2(6) . . ?
F3 C105 C104 118.7(6) . . ?
C106 C105 C104 121.1(5) . . ?
F4 C106 C105 117.4(5) . . ?
F4 C106 C101 120.2(6) . . ?
C105 C106 C101 122.4(5) . . ?
C7 N1 C8 120.1(4) . . ?
C2 O1 H1 101(3) . . ?
C3 O2 C18 117.7(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O1 179.8(4) . . . . ?
C7 C1 C2 O1 0.7(7) . . . . ?
C6 C1 C2 C3 -0.8(6) . . . . ?
C7 C1 C2 C3 -180.0(4) . . . . ?
O1 C2 C3 O2 -1.6(6) . . . . ?
C1 C2 C3 O2 179.0(4) . . . . ?
O1 C2 C3 C4 -179.7(4) . . . . ?
C1 C2 C3 C4 0.9(7) . . . . ?
O2 C3 C4 C5 -178.5(5) . . . . ?
C2 C3 C4 C5 -0.6(8) . . . . ?
C3 C4 C5 C6 0.1(9) . . . . ?
C4 C5 C6 C1 0.0(8) . . . . ?
C2 C1 C6 C5 0.4(7) . . . . ?
C7 C1 C6 C5 179.5(5) . . . . ?
C2 C1 C7 N1 -0.9(7) . . . . ?
C6 C1 C7 N1 180.0(4) . . . . ?
C17 C8 C9 C10 -179.0(4) . . . . ?
N1 C8 C9 C10 2.9(6) . . . . ?
C17 C8 C9 C14 -0.8(6) . . . . ?
N1 C8 C9 C14 -178.9(4) . . . . ?
C8 C9 C10 C11 178.9(4) . . . . ?
C14 C9 C10 C11 0.6(6) . . . . ?
C9 C10 C11 C12 0.0(8) . . . . ?
C10 C11 C12 C13 -0.3(9) . . . . ?
C11 C12 C13 C14 -0.1(8) . . . . ?
C12 C13 C14 C15 -178.6(5) . . . . ?
C12 C13 C14 C9 0.6(7) . . . . ?
C8 C9 C14 C15 0.0(6) . . . . ?
C10 C9 C14 C15 178.4(4) . . . . ?
C8 C9 C14 C13 -179.2(4) . . . . ?
C10 C9 C14 C13 -0.9(6) . . . . ?
C13 C14 C15 C16 178.3(5) . . . . ?
C9 C14 C15 C16 -0.9(7) . . . . ?
C14 C15 C16 C17 2.5(8) . . . . ?
C9 C8 C17 C16 2.4(7) . . . . ?
N1 C8 C17 C16 -179.6(4) . . . . ?
C15 C16 C17 C8 -3.2(8) . . . . ?
C106 C101 C102 F1 -178.6(5) . . . . ?
I1 C101 C102 F1 1.8(7) . . . . ?
C106 C101 C102 C103 1.4(8) . . . . ?
I1 C101 C102 C103 -178.2(4) . . . . ?
F1 C102 C103 F2 -1.9(8) . . . . ?
C101 C102 C103 F2 178.1(5) . . . . ?
F1 C102 C103 C104 179.2(5) . . . . ?
C101 C102 C103 C104 -0.8(9) . . . . ?
F2 C103 C104 C105 -178.8(5) . . . . ?
C102 C103 C104 C105 0.1(8) . . . . ?
F2 C103 C104 I2 -3.7(7) . . . . ?
C102 C103 C104 I2 175.1(4) . . . . ?
C103 C104 C105 F3 178.6(5) . . . . ?
I2 C104 C105 F3 3.5(8) . . . . ?
C103 C104 C105 C106 -0.2(8) . . . . ?
I2 C104 C105 C106 -175.2(4) . . . . ?
F3 C105 C106 F4 0.0(9) . . . . ?
C104 C105 C106 F4 178.7(5) . . . . ?
F3 C105 C106 C101 -177.8(5) . . . . ?
C104 C105 C106 C101 0.9(9) . . . . ?
C102 C101 C106 F4 -179.2(5) . . . . ?
I1 C101 C106 F4 0.4(7) . . . . ?
C102 C101 C106 C105 -1.5(8) . . . . ?
I1 C101 C106 C105 178.1(5) . . . . ?
C1 C7 N1 C8 -176.7(4) . . . . ?
C17 C8 N1 C7 46.8(6) . . . . ?
C9 C8 N1 C7 -135.0(4) . . . . ?
C4 C3 O2 C18 -7.8(8) . . . . ?
C2 C3 O2 C18 174.2(5) . . . . ?

_refine_diff_density_max         1.052
_refine_diff_density_min         -1.076
_refine_diff_density_rms         0.073


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

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1549339'
#Added by publCIF



_audit_update_record             
;
2017-05-11 deposited with the CCDC.
2017-08-18 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  graphite
#Added by publCIF




_symmetry_space_group_name_hall  'P 2yb'
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(2-Methoxy-6-(naphthalen-1-yliminomethyl)-phenol)(1,3-diiodotetrafluorobenzene)
_chemical_name_common            
(2-Methoxy-6-(naphthalen-1-yliminomethyl)-phenol)(1,3-diiodotetrafluorobenzene)
_chemical_melting_point          ?
_chemical_formula_moiety         (C18H15NO2)(C6F4I2)
_chemical_formula_sum            'C24 H15 F4 I2 N O2'
_chemical_formula_weight         679.17

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'
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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   6.5387(3)
_cell_length_b                   15.6854(6)
_cell_length_c                   11.6872(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.614(4)
_cell_angle_gamma                90
_cell_volume                     1181.83(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3188
_cell_measurement_theta_min      3.7604
_cell_measurement_theta_max      32.1065

_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.909
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.433
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.053
_exptl_absorpt_coefficient_mu    2.714
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.27646
_exptl_absorpt_correction_T_max  0.63329
_exptl_absorpt_process_details   
;
CrysAlis RED (Oxford Diffraction, 2010), based on expressions derived by Clark
and Ried (1995)
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Kappa CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7305
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.768
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.792
_diffrn_reflns_point_group_measured_fraction_full 0.806
_reflns_number_total             4085
_reflns_number_gt                2729
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.534
_reflns_Friedel_fraction_max     0.572
_reflns_Friedel_fraction_full    0.601

_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)+(0.0486P)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         4085
_refine_ls_number_parameters     299
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0860
_refine_ls_wR_factor_gt          0.0800
_refine_ls_goodness_of_fit_ref   0.876
_refine_ls_restrained_S_all      0.876
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0969(11) 0.2630(6) 0.9415(6) 0.0433(18) Uani 1 1 d . . . . .
C2 C 0.0282(11) 0.3081(5) 1.0299(6) 0.0376(18) Uani 1 1 d . . . . .
C3 C -0.1539(12) 0.3570(6) 1.0064(7) 0.0445(19) Uani 1 1 d . . . . .
C4 C -0.2595(13) 0.3606(6) 0.8940(8) 0.053(2) Uani 1 1 d . . . . .
H4 H -0.3815 0.3921 0.8781 0.063 Uiso 1 1 calc R U . . .
C5 C -0.1892(15) 0.3192(6) 0.8059(8) 0.060(3) Uani 1 1 d . . . . .
H5 H -0.2606 0.3245 0.7305 0.071 Uiso 1 1 calc R U . . .
C6 C -0.0127(13) 0.2692(7) 0.8274(7) 0.055(2) Uani 1 1 d . . . . .
H6 H 0.0331 0.2401 0.7671 0.066 Uiso 1 1 calc R U . . .
C13 C 0.7056(16) -0.0331(7) 1.3148(9) 0.064(3) Uani 1 1 d . . . . .
H13 H 0.8147 -0.0714 1.3339 0.077 Uiso 1 1 calc R U . . .
C14 C 0.5553(18) -0.0296(7) 1.3794(9) 0.073(3) Uani 1 1 d . . . . .
H14 H 0.5612 -0.0656 1.4432 0.088 Uiso 1 1 calc R U . . .
C15 C 0.3879(15) 0.0278(7) 1.3527(8) 0.062(3) Uani 1 1 d . . . . .
H15 H 0.2828 0.0283 1.3974 0.074 Uiso 1 1 calc R U . . .
C17 C -0.4078(15) 0.4325(8) 1.0922(11) 0.085(4) Uani 1 1 d . . . . .
H17A H -0.4212 0.4793 1.0386 0.127 Uiso 1 1 calc R U . . .
H17B H -0.4294 0.4523 1.1669 0.127 Uiso 1 1 calc R U . . .
H17C H -0.5093 0.3897 1.0647 0.127 Uiso 1 1 calc R U . . .
O1 O 0.1265(8) 0.3053(4) 1.1418(4) 0.0497(14) Uani 1 1 d . . . . .
H1 H 0.2279 0.2739 1.1467 0.075 Uiso 1 1 calc R U . . .
O2 O -0.2066(9) 0.3970(5) 1.1015(5) 0.0618(17) Uani 1 1 d . . . . .
C7 C 0.2707(12) 0.2061(6) 0.9658(7) 0.047(2) Uani 1 1 d . . . . .
H7 H 0.3151 0.1774 0.9048 0.057 Uiso 1 1 calc R U . . .
C8 C 0.5325(12) 0.1348(5) 1.0923(8) 0.044(2) Uani 1 1 d . . . . .
C9 C 0.6852(12) 0.1304(6) 1.0266(8) 0.048(2) Uani 1 1 d . . . . .
H9 H 0.6825 0.1660 0.9628 0.057 Uiso 1 1 calc R U . . .
C10 C 0.8453(14) 0.0720(6) 1.0559(9) 0.058(2) Uani 1 1 d . . . . .
H10 H 0.9506 0.0697 1.0114 0.070 Uiso 1 1 calc R U . . .
C11 C 0.8523(13) 0.0186(7) 1.1469(9) 0.064(3) Uani 1 1 d . . . . .
H11 H 0.9605 -0.0204 1.1627 0.076 Uiso 1 1 calc R U . . .
C12 C 0.6994(12) 0.0205(6) 1.2183(8) 0.052(2) Uani 1 1 d . . . . .
C16 C 0.3804(13) 0.0823(6) 1.2618(8) 0.052(2) Uani 1 1 d . . . . .
H16 H 0.2716 0.1210 1.2457 0.063 Uiso 1 1 calc R U . . .
C101 C 0.7433(13) 0.2052(6) 0.4641(7) 0.047(2) Uani 1 1 d . . . . .
C102 C 0.8270(14) 0.1375(6) 0.5297(8) 0.054(2) Uani 1 1 d . . . . .
C103 C 0.7374(15) 0.1032(6) 0.6176(7) 0.052(2) Uani 1 1 d . . . . .
C104 C 0.5566(16) 0.1397(7) 0.6382(8) 0.061(3) Uani 1 1 d . . . . .
C105 C 0.4655(14) 0.2069(7) 0.5734(9) 0.056(2) Uani 1 1 d . . . . .
C106 C 0.5586(13) 0.2385(6) 0.4868(8) 0.054(2) Uani 1 1 d . . . . .
C217 C 0.5358(12) 0.0809(5) 1.1917(7) 0.043(2) Uani 1 1 d . . . . .
N1 N 0.3669(9) 0.1939(4) 1.0705(6) 0.0423(16) Uani 1 1 d . . . . .
F1 F 1.0042(9) 0.1031(4) 0.5084(5) 0.0690(15) Uani 1 1 d . . . . .
F2 F 0.4607(10) 0.1101(5) 0.7241(5) 0.0858(19) Uani 1 1 d . . . . .
F3 F 0.2919(8) 0.2419(5) 0.5991(5) 0.0854(18) Uani 1 1 d . . . . .
F4 F 0.4678(10) 0.3036(4) 0.4236(5) 0.0801(17) Uani 1 1 d . . . . .
I1 I 0.88456(10) 0.25674(4) 0.33101(5) 0.0678(2) Uani 1 1 d . . . . .
I2 I 0.87324(12) 0.00389(5) 0.71896(6) 0.0825(3) 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
C1 C2 1.387(11) . ?
C1 C6 1.409(10) . ?
C1 C7 1.435(12) . ?
C2 O1 1.358(8) . ?
C2 C3 1.404(11) . ?
C3 O2 1.369(10) . ?
C3 C4 1.379(12) . ?
C4 C5 1.361(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(13) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C13 C14 1.337(14) . ?
C13 C12 1.402(13) . ?
C13 H13 0.9300 . ?
C14 C15 1.411(14) . ?
C14 H14 0.9300 . ?
C15 C16 1.359(13) . ?
C15 H15 0.9300 . ?
C17 O2 1.416(10) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O1 H1 0.8200 . ?
C7 N1 1.293(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.359(11) . ?
C8 N1 1.416(10) . ?
C8 C217 1.435(12) . ?
C9 C10 1.390(12) . ?
C9 H9 0.9300 . ?
C10 C11 1.349(14) . ?
C10 H10 0.9300 . ?
C11 C12 1.406(12) . ?
C11 H11 0.9300 . ?
C12 C217 1.423(12) . ?
C16 C217 1.408(12) . ?
C16 H16 0.9300 . ?
C101 C102 1.369(13) . ?
C101 C106 1.382(12) . ?
C101 I1 2.099(8) . ?
C102 F1 1.338(11) . ?
C102 C103 1.375(12) . ?
C103 C104 1.371(13) . ?
C103 I2 2.065(10) . ?
C104 F2 1.352(11) . ?
C104 C105 1.374(14) . ?
C105 F3 1.340(10) . ?
C105 C106 1.359(13) . ?
C106 F4 1.338(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.6(8) . . ?
C2 C1 C7 120.9(7) . . ?
C6 C1 C7 119.4(8) . . ?
O1 C2 C1 122.7(7) . . ?
O1 C2 C3 117.1(7) . . ?
C1 C2 C3 120.2(7) . . ?
O2 C3 C4 126.8(7) . . ?
O2 C3 C2 114.4(7) . . ?
C4 C3 C2 118.8(8) . . ?
C5 C4 C3 121.5(8) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 120.7(8) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.2(8) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C14 C13 C12 120.3(9) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 121.2(10) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 120.0(9) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 O1 H1 109.5 . . ?
C3 O2 C17 118.3(7) . . ?
N1 C7 C1 121.6(7) . . ?
N1 C7 H7 119.2 . . ?
C1 C7 H7 119.2 . . ?
C9 C8 N1 122.9(8) . . ?
C9 C8 C217 120.9(8) . . ?
N1 C8 C217 116.1(8) . . ?
C8 C9 C10 119.3(9) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 121.9(9) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 121.4(9) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 122.5(9) . . ?
C13 C12 C217 119.7(8) . . ?
C11 C12 C217 117.9(9) . . ?
C15 C16 C217 120.6(9) . . ?
C15 C16 H16 119.7 . . ?
C217 C16 H16 119.7 . . ?
C102 C101 C106 117.8(8) . . ?
C102 C101 I1 122.0(7) . . ?
C106 C101 I1 120.2(7) . . ?
F1 C102 C101 119.1(8) . . ?
F1 C102 C103 118.1(9) . . ?
C101 C102 C103 122.8(9) . . ?
C104 C103 C102 117.1(9) . . ?
C104 C103 I2 121.0(7) . . ?
C102 C103 I2 121.9(7) . . ?
F2 C104 C103 120.5(10) . . ?
F2 C104 C105 117.5(9) . . ?
C103 C104 C105 122.0(9) . . ?
F3 C105 C106 121.3(10) . . ?
F3 C105 C104 119.7(9) . . ?
C106 C105 C104 119.0(8) . . ?
F4 C106 C105 118.5(8) . . ?
F4 C106 C101 120.3(9) . . ?
C105 C106 C101 121.2(9) . . ?
C16 C217 C12 118.2(8) . . ?
C16 C217 C8 123.1(8) . . ?
C12 C217 C8 118.6(8) . . ?
C7 N1 C8 120.3(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O1 -179.8(8) . . . . ?
C7 C1 C2 O1 3.9(12) . . . . ?
C6 C1 C2 C3 2.5(12) . . . . ?
C7 C1 C2 C3 -173.8(8) . . . . ?
O1 C2 C3 O2 1.0(10) . . . . ?
C1 C2 C3 O2 178.8(8) . . . . ?
O1 C2 C3 C4 -179.2(8) . . . . ?
C1 C2 C3 C4 -1.4(12) . . . . ?
O2 C3 C4 C5 178.7(9) . . . . ?
C2 C3 C4 C5 -1.1(13) . . . . ?
C3 C4 C5 C6 2.5(14) . . . . ?
C4 C5 C6 C1 -1.4(14) . . . . ?
C2 C1 C6 C5 -1.1(13) . . . . ?
C7 C1 C6 C5 175.2(8) . . . . ?
C12 C13 C14 C15 -0.1(15) . . . . ?
C13 C14 C15 C16 -1.8(15) . . . . ?
C4 C3 O2 C17 13.5(14) . . . . ?
C2 C3 O2 C17 -166.8(9) . . . . ?
C2 C1 C7 N1 1.1(12) . . . . ?
C6 C1 C7 N1 -175.1(8) . . . . ?
N1 C8 C9 C10 178.3(8) . . . . ?
C217 C8 C9 C10 0.7(13) . . . . ?
C8 C9 C10 C11 0.9(14) . . . . ?
C9 C10 C11 C12 -1.3(14) . . . . ?
C14 C13 C12 C11 -179.3(9) . . . . ?
C14 C13 C12 C217 2.1(14) . . . . ?
C10 C11 C12 C13 -178.7(9) . . . . ?
C10 C11 C12 C217 0.0(13) . . . . ?
C14 C15 C16 C217 1.6(14) . . . . ?
C106 C101 C102 F1 179.0(8) . . . . ?
I1 C101 C102 F1 0.0(11) . . . . ?
C106 C101 C102 C103 -1.3(13) . . . . ?
I1 C101 C102 C103 179.7(7) . . . . ?
F1 C102 C103 C104 179.7(8) . . . . ?
C101 C102 C103 C104 0.0(13) . . . . ?
F1 C102 C103 I2 2.0(11) . . . . ?
C101 C102 C103 I2 -177.7(7) . . . . ?
C102 C103 C104 F2 -179.2(8) . . . . ?
I2 C103 C104 F2 -1.5(12) . . . . ?
C102 C103 C104 C105 1.0(14) . . . . ?
I2 C103 C104 C105 178.7(7) . . . . ?
F2 C104 C105 F3 2.0(14) . . . . ?
C103 C104 C105 F3 -178.1(8) . . . . ?
F2 C104 C105 C106 179.6(8) . . . . ?
C103 C104 C105 C106 -0.5(14) . . . . ?
F3 C105 C106 F4 -3.0(13) . . . . ?
C104 C105 C106 F4 179.5(8) . . . . ?
F3 C105 C106 C101 176.7(8) . . . . ?
C104 C105 C106 C101 -0.9(14) . . . . ?
C102 C101 C106 F4 -178.6(8) . . . . ?
I1 C101 C106 F4 0.4(11) . . . . ?
C102 C101 C106 C105 1.8(13) . . . . ?
I1 C101 C106 C105 -179.2(7) . . . . ?
C15 C16 C217 C12 0.4(12) . . . . ?
C15 C16 C217 C8 177.8(8) . . . . ?
C13 C12 C217 C16 -2.2(12) . . . . ?
C11 C12 C217 C16 179.1(8) . . . . ?
C13 C12 C217 C8 -179.8(8) . . . . ?
C11 C12 C217 C8 1.5(11) . . . . ?
C9 C8 C217 C16 -179.3(7) . . . . ?
N1 C8 C217 C16 2.9(12) . . . . ?
C9 C8 C217 C12 -1.9(12) . . . . ?
N1 C8 C217 C12 -179.6(7) . . . . ?
C1 C7 N1 C8 177.4(8) . . . . ?
C9 C8 N1 C7 44.9(11) . . . . ?
C217 C8 N1 C7 -137.4(8) . . . . ?

_refine_diff_density_max         0.630
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.075


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

data_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1558834'
#Added by publCIF



_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-08-18 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  graphite
#Added by publCIF




_symmetry_space_group_name_hall  '-P 2ac 2ab'
# publcif _publ_body_element loop end

# start Validation Reply Form
_vrf_PLAT026_shelx               
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low 28 %

RESPONSE: This low ratio is caused by very low resolution i.e. >0.9 and caused
 by the nature of the material, no atom heavier than oxygen but also a very
 thin crystal. 
;

_vrf_PLAT910_shelx               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min) 12 Note

RESPONSE: This can be explained with low diffraction intensities and very thin
 crystal.
;

# end Validation Reply Form 

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2-(Adamantan-1-yliminomethyl)-6-methoxy-phenol
_chemical_name_common            
2-(Adamantan-1-yliminomethyl)-6-methoxy-phenol
_chemical_melting_point          ?
_chemical_formula_moiety         C18H23N1O2
_chemical_formula_sum            'C18 H23 N O2'
_chemical_formula_weight         285.37

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   7.1326(7)
_cell_length_b                   13.0545(9)
_cell_length_c                   34.263(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3190.3(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1228
_cell_measurement_theta_min      3.8800
_cell_measurement_theta_max      40.9713

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   0.663
_exptl_crystal_size_max          0.336
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81571
_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      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Kappa CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14447
_diffrn_reflns_av_unetI/netI     0.2285
_diffrn_reflns_av_R_equivalents  0.1351
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         3.925
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2793
_reflns_number_gt                791
_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)+(0.0197P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2793
_refine_ls_number_parameters     195
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1862
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.0674
_refine_ls_wR_factor_gt          0.0546
_refine_ls_goodness_of_fit_ref   0.620
_refine_ls_restrained_S_all      0.620
_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
O1 O -0.2381(4) 0.31956(16) 0.65114(7) 0.0743(8) Uani 1 1 d . . . . .
O2 O -0.5163(3) 0.37896(16) 0.69533(6) 0.0799(7) Uani 1 1 d . . . . .
N1 N -0.0256(3) 0.17171(16) 0.62527(6) 0.0523(7) Uani 1 1 d . . . . .
C1 C -0.2570(4) 0.1467(2) 0.67471(8) 0.0431(7) Uani 1 1 d . . . . .
C2 C -0.3144(4) 0.2486(2) 0.67472(8) 0.0490(8) Uani 1 1 d . . . . .
C5 C -0.4832(4) 0.1087(2) 0.72454(7) 0.0577(8) Uani 1 1 d . . . . .
H5 H -0.5372 0.0619 0.7417 0.069 Uiso 1 1 calc R U . . .
C6 C -0.3439(4) 0.0788(2) 0.69987(8) 0.0552(8) Uani 1 1 d . . . . .
H6 H -0.3060 0.0106 0.6999 0.066 Uiso 1 1 calc R U . . .
C7 C -0.1085(4) 0.1115(2) 0.64877(8) 0.0503(8) Uani 1 1 d . . . . .
H7 H -0.0733 0.0429 0.6494 0.060 Uiso 1 1 calc R U . . .
C4 C -0.5438(4) 0.2097(3) 0.72384(7) 0.0617(9) Uani 1 1 d . . . . .
H4 H -0.6401 0.2306 0.7403 0.074 Uiso 1 1 calc R U . . .
C9 C 0.1206(4) 0.13387(19) 0.59880(8) 0.0475(8) Uani 1 1 d . U . . .
C3 C -0.4619(5) 0.2789(2) 0.69887(9) 0.0522(8) Uani 1 1 d . . . . .
C8 C -0.6970(5) 0.4055(2) 0.70905(8) 0.1032(13) Uani 1 1 d . . . . .
H8A H -0.7891 0.3633 0.6964 0.155 Uiso 1 1 calc R U . . .
H8B H -0.7217 0.4761 0.7033 0.155 Uiso 1 1 calc R U . . .
H8C H -0.7028 0.3950 0.7368 0.155 Uiso 1 1 calc R U . . .
C10 C 0.0574(4) 0.1620(2) 0.55816(8) 0.0838(11) Uani 1 1 d . . . . .
H10A H 0.0322 0.2349 0.5568 0.101 Uiso 1 1 calc R U . . .
H10B H -0.0574 0.1257 0.5519 0.101 Uiso 1 1 calc R U . . .
C18 C 0.1568(4) 0.01919(18) 0.59940(9) 0.0913(12) Uani 1 1 d . U . . .
H18A H 0.0431 -0.0173 0.5925 0.110 Uiso 1 1 calc R U . . .
H18B H 0.1939 -0.0019 0.6254 0.110 Uiso 1 1 calc R U . . .
C14 C 0.3006(5) 0.1885(2) 0.60865(8) 0.0845(11) Uani 1 1 d . . . . .
H14A H 0.3408 0.1692 0.6347 0.101 Uiso 1 1 calc R U . . .
H14B H 0.2797 0.2619 0.6084 0.101 Uiso 1 1 calc R U . . .
C11 C 0.2154(6) 0.1328(4) 0.52781(9) 0.0903(12) Uani 1 1 d . . . . .
H11 H 0.1757 0.1510 0.5013 0.108 Uiso 1 1 calc R U . . .
C15 C 0.2466(5) 0.0197(3) 0.53074(11) 0.0936(12) Uani 1 1 d . . . . .
H15A H 0.1300 -0.0161 0.5256 0.112 Uiso 1 1 calc R U . . .
H15B H 0.3375 -0.0016 0.5113 0.112 Uiso 1 1 calc R U . . .
C17 C 0.4873(5) 0.0478(3) 0.58078(9) 0.0906(11) Uani 1 1 d . . . . .
H17A H 0.5882 0.0287 0.5632 0.109 Uiso 1 1 calc R U . . .
H17B H 0.5238 0.0287 0.6071 0.109 Uiso 1 1 calc R U . . .
C16 C 0.3149(6) -0.0072(2) 0.56980(12) 0.0863(12) Uani 1 1 d . U . . .
H16 H 0.3391 -0.0811 0.5707 0.104 Uiso 1 1 calc R U . . .
C12 C 0.3896(6) 0.1930(3) 0.53902(12) 0.1036(14) Uani 1 1 d . . . . .
H12A H 0.4878 0.1809 0.5200 0.124 Uiso 1 1 calc R U . . .
H12B H 0.3612 0.2656 0.5391 0.124 Uiso 1 1 calc R U . . .
C13 C 0.4560(5) 0.1606(3) 0.57878(11) 0.0849(11) Uani 1 1 d . . . . .
H13 H 0.5721 0.1969 0.5854 0.102 Uiso 1 1 calc R U . . .
H1O H -0.154(4) 0.296(2) 0.6390(8) 0.080(14) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.344(3) . ?
O1 H1O 0.79(3) . ?
O2 C3 1.369(3) . ?
O2 C8 1.415(3) . ?
N1 C7 1.271(3) . ?
N1 C9 1.468(3) . ?
C1 C6 1.383(3) . ?
C1 C2 1.392(3) . ?
C1 C7 1.457(3) . ?
C2 C3 1.396(3) . ?
C5 C6 1.362(3) . ?
C5 C4 1.388(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C4 C3 1.374(3) . ?
C4 H4 0.9300 . ?
C9 C14 1.507(3) . ?
C9 C10 1.509(3) . ?
C9 C18 1.519(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 C11 1.580(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C18 C16 1.555(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C14 C13 1.552(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C11 C15 1.496(4) . ?
C11 C12 1.519(4) . ?
C11 H11 0.9800 . ?
C15 C16 1.467(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C17 C16 1.473(4) . ?
C17 C13 1.492(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C16 H16 0.9800 . ?
C12 C13 1.503(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13 0.9800 . ?

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 110(2) . . ?
C3 O2 C8 117.5(2) . . ?
C7 N1 C9 120.9(2) . . ?
C6 C1 C2 118.7(3) . . ?
C6 C1 C7 120.3(3) . . ?
C2 C1 C7 121.0(3) . . ?
O1 C2 C1 122.7(3) . . ?
O1 C2 C3 117.8(3) . . ?
C1 C2 C3 119.5(3) . . ?
C6 C5 C4 119.3(3) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 122.0(3) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
N1 C7 C1 122.0(2) . . ?
N1 C7 H7 119.0 . . ?
C1 C7 H7 119.0 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C9 C14 107.9(2) . . ?
N1 C9 C10 106.0(2) . . ?
C14 C9 C10 110.2(2) . . ?
N1 C9 C18 116.4(2) . . ?
C14 C9 C18 108.6(3) . . ?
C10 C9 C18 107.6(2) . . ?
O2 C3 C4 124.2(3) . . ?
O2 C3 C2 115.6(3) . . ?
C4 C3 C2 120.2(3) . . ?
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 . . ?
C9 C10 C11 109.6(3) . . ?
C9 C10 H10A 109.8 . . ?
C11 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
C11 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C9 C18 C16 109.5(2) . . ?
C9 C18 H18A 109.8 . . ?
C16 C18 H18A 109.8 . . ?
C9 C18 H18B 109.8 . . ?
C16 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
C9 C14 C13 110.5(2) . . ?
C9 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C15 C11 C12 111.8(3) . . ?
C15 C11 C10 107.5(3) . . ?
C12 C11 C10 107.0(3) . . ?
C15 C11 H11 110.2 . . ?
C12 C11 H11 110.2 . . ?
C10 C11 H11 110.2 . . ?
C16 C15 C11 110.3(3) . . ?
C16 C15 H15A 109.6 . . ?
C11 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C11 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C16 C17 C13 110.2(3) . . ?
C16 C17 H17A 109.6 . . ?
C13 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
C13 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C15 C16 C17 113.2(3) . . ?
C15 C16 C18 107.5(3) . . ?
C17 C16 C18 109.3(3) . . ?
C15 C16 H16 108.9 . . ?
C17 C16 H16 108.9 . . ?
C18 C16 H16 108.9 . . ?
C13 C12 C11 110.0(3) . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C17 C13 C12 111.5(3) . . ?
C17 C13 C14 107.9(3) . . ?
C12 C13 C14 107.9(3) . . ?
C17 C13 H13 109.8 . . ?
C12 C13 H13 109.8 . . ?
C14 C13 H13 109.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O1 -179.8(3) . . . . ?
C7 C1 C2 O1 0.2(4) . . . . ?
C6 C1 C2 C3 -2.4(4) . . . . ?
C7 C1 C2 C3 177.5(3) . . . . ?
C4 C5 C6 C1 1.7(4) . . . . ?
C2 C1 C6 C5 0.0(4) . . . . ?
C7 C1 C6 C5 -180.0(3) . . . . ?
C9 N1 C7 C1 -178.6(2) . . . . ?
C6 C1 C7 N1 180.0(3) . . . . ?
C2 C1 C7 N1 0.1(4) . . . . ?
C6 C5 C4 C3 -0.9(4) . . . . ?
C7 N1 C9 C14 -118.4(3) . . . . ?
C7 N1 C9 C10 123.4(3) . . . . ?
C7 N1 C9 C18 3.8(4) . . . . ?
C8 O2 C3 C4 -19.0(4) . . . . ?
C8 O2 C3 C2 160.4(3) . . . . ?
C5 C4 C3 O2 177.9(3) . . . . ?
C5 C4 C3 C2 -1.5(4) . . . . ?
O1 C2 C3 O2 1.2(4) . . . . ?
C1 C2 C3 O2 -176.3(2) . . . . ?
O1 C2 C3 C4 -179.3(3) . . . . ?
C1 C2 C3 C4 3.2(4) . . . . ?
N1 C9 C10 C11 175.1(3) . . . . ?
C14 C9 C10 C11 58.5(3) . . . . ?
C18 C9 C10 C11 -59.8(4) . . . . ?
N1 C9 C18 C16 180.0(3) . . . . ?
C14 C9 C18 C16 -58.1(4) . . . . ?
C10 C9 C18 C16 61.3(4) . . . . ?
N1 C9 C14 C13 -173.9(3) . . . . ?
C10 C9 C14 C13 -58.5(3) . . . . ?
C18 C9 C14 C13 59.2(3) . . . . ?
C9 C10 C11 C15 60.2(4) . . . . ?
C9 C10 C11 C12 -60.1(4) . . . . ?
C12 C11 C15 C16 54.3(4) . . . . ?
C10 C11 C15 C16 -62.8(4) . . . . ?
C11 C15 C16 C17 -56.5(4) . . . . ?
C11 C15 C16 C18 64.4(4) . . . . ?
C13 C17 C16 C15 57.5(4) . . . . ?
C13 C17 C16 C18 -62.3(4) . . . . ?
C9 C18 C16 C15 -63.2(4) . . . . ?
C9 C18 C16 C17 60.0(4) . . . . ?
C15 C11 C12 C13 -54.1(4) . . . . ?
C10 C11 C12 C13 63.3(4) . . . . ?
C16 C17 C13 C12 -56.4(4) . . . . ?
C16 C17 C13 C14 61.9(4) . . . . ?
C11 C12 C13 C17 55.0(4) . . . . ?
C11 C12 C13 C14 -63.4(4) . . . . ?
C9 C14 C13 C17 -60.6(4) . . . . ?
C9 C14 C13 C12 60.0(4) . . . . ?

_refine_diff_density_max         0.136
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.025


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

data_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1558871'
#Added by publCIF



_audit_update_record             
;
2017-06-29 deposited with the CCDC.
2017-08-18 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  graphite
#Added by publCIF




_symmetry_space_group_name_hall  '-P 1'
# publcif _publ_body_element loop end

# start Validation Reply Form
_vrf_PLAT910_shelx               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          12 Note  
RESPONSE: This due to deleted (overflow) reflections at low angles which can be
 explained with high diffraction intensities.
;
# end Validation Reply Form 

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
bis(2-(Adamantan-1-yliminomethyl)-6-methoxy-phenol)(14-diiodotetrafluorobenzene)
_chemical_name_common            
bis(2-(Adamantan-1-yliminomethyl)-6-methoxy-phenol)(14-diiodotetrafluorobenzene)
_chemical_melting_point          ?
_chemical_formula_moiety         (C18H23N1O2)2(C6F4I2)
_chemical_formula_sum            'C42 H46 F4 I2 N2 O4'
_chemical_formula_weight         972.63

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                   9.2260(4)
_cell_length_b                   10.0931(4)
_cell_length_c                   12.4702(4)
_cell_angle_alpha                95.431(3)
_cell_angle_beta                 95.804(3)
_cell_angle_gamma                116.039(4)
_cell_volume                     1025.36(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8560
_cell_measurement_theta_min      3.8156
_cell_measurement_theta_max      40.7034

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_F_000             486
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.559
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    1.594
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.57679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Kappa CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16969
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.063
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4442
_reflns_number_gt                3369
_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)+(0.1152P)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         4442
_refine_ls_number_parameters     245
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1586
_refine_ls_wR_factor_gt          0.1534
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001

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
C8 C 0.5161(9) 0.7404(9) 0.6539(5) 0.0767(11) Uani 1 1 d . U . . .
C9 C 0.4875(13) 0.8714(11) 0.6823(8) 0.1036(19) Uani 1 1 d . U . . .
H12A H 0.4279 0.8855 0.6194 0.124 Uiso 1 1 calc R U . . .
H12B H 0.5913 0.9603 0.7034 0.124 Uiso 1 1 calc R U . . .
C10 C 0.3814(13) 0.8451(12) 0.7843(8) 0.111(2) Uani 1 1 d . U . . .
H22 H 0.3541 0.9269 0.8040 0.133 Uiso 1 1 calc R U . . .
C11 C 0.2228(15) 0.6918(13) 0.7244(10) 0.120(2) Uani 1 1 d . U . . .
H24A H 0.1338 0.6734 0.7655 0.144 Uiso 1 1 calc R U . . .
H24B H 0.1886 0.7067 0.6523 0.144 Uiso 1 1 calc R U . . .
C12 C 0.2506(14) 0.5581(13) 0.7133(9) 0.1105(18) Uani 1 1 d . U . . .
H23 H 0.1495 0.4645 0.6927 0.133 Uiso 1 1 calc R U . . .
C13 C 0.3591(12) 0.5992(11) 0.6187(8) 0.1020(19) Uani 1 1 d . U . . .
H11A H 0.3841 0.5177 0.5968 0.122 Uiso 1 1 calc R U . . .
H11B H 0.2971 0.6109 0.5560 0.122 Uiso 1 1 calc R U . . .
C14 C 0.6114(10) 0.7300(10) 0.7590(6) 0.0855(18) Uani 1 1 d . U . . .
H13A H 0.7106 0.8226 0.7826 0.103 Uiso 1 1 calc R U . . .
H13B H 0.6414 0.6497 0.7456 0.103 Uiso 1 1 calc R U . . .
C15 C 0.4959(12) 0.6984(12) 0.8522(7) 0.102(2) Uani 1 1 d . U . . .
H14 H 0.5528 0.6879 0.9191 0.123 Uiso 1 1 calc R U . . .
C16 C 0.3508(14) 0.5618(10) 0.8123(8) 0.111(3) Uani 1 1 d . . . . .
H21A H 0.2836 0.5390 0.8694 0.133 Uiso 1 1 calc R U . . .
H21B H 0.3826 0.4826 0.7996 0.133 Uiso 1 1 calc R U . . .
C17 C 0.4707(13) 0.8225(12) 0.8703(8) 0.107(3) Uani 1 1 d . U . . .
H20A H 0.5763 0.9097 0.8891 0.129 Uiso 1 1 calc R U . . .
H20B H 0.4149 0.8152 0.9330 0.129 Uiso 1 1 calc R U . . .
C18 C 0.8600(10) 0.9282(12) 0.1125(6) 0.097(3) Uani 1 1 d . . . . .
H15A H 0.9702 1.0037 0.1375 0.146 Uiso 1 1 calc R U . . .
H15B H 0.8048 0.9655 0.0636 0.146 Uiso 1 1 calc R U . . .
H15C H 0.8614 0.8413 0.0749 0.146 Uiso 1 1 calc R U . . .
C101 C 0.1408(6) 0.5731(6) 0.0802(4) 0.0439(10) Uani 1 1 d . . . . .
C102 C 0.0635(6) 0.4198(6) 0.0522(4) 0.0476(11) Uani 1 1 d . . . . .
C103 C 0.0739(6) 0.6518(5) 0.0263(4) 0.0465(11) Uani 1 1 d . . . . .
N1 N 0.6120(5) 0.7717(5) 0.5636(3) 0.0497(10) Uani 1 1 d . . . . .
F1 F 0.1434(4) 0.8011(3) 0.0489(3) 0.0631(8) Uani 1 1 d . . . . .
F2 F 0.1218(4) 0.3368(4) 0.1017(3) 0.0674(9) Uani 1 1 d . . . . .
C1 C 0.7664(6) 0.8324(5) 0.3787(4) 0.0446(10) Uani 1 1 d . . . . .
C2 C 0.8556(6) 0.8623(6) 0.2901(4) 0.0478(11) Uani 1 1 d . . . . .
C3 C 1.0031(7) 0.8614(6) 0.2963(5) 0.0570(13) Uani 1 1 d . . . . .
H3 H 1.0588 0.8800 0.2370 0.068 Uiso 1 1 calc R U . . .
C4 C 1.0724(7) 0.8326(8) 0.3916(5) 0.0664(15) Uani 1 1 d . . . . .
H4 H 1.1729 0.8314 0.3949 0.080 Uiso 1 1 calc R U . . .
C5 C 0.9920(8) 0.8065(8) 0.4785(5) 0.0654(15) Uani 1 1 d . . . . .
H5 H 1.0395 0.7905 0.5422 0.079 Uiso 1 1 calc R U . . .
C6 C 0.8373(6) 0.8035(6) 0.4733(4) 0.0500(11) Uani 1 1 d . . . . .
C7 C 0.7521(7) 0.7743(6) 0.5659(4) 0.0544(12) Uani 1 1 d . . . . .
H8 H 0.8003 0.7570 0.6287 0.065 Uiso 1 1 calc R U . . .
O1 O 0.6233(5) 0.8315(5) 0.3703(3) 0.0578(9) Uani 1 1 d . . . . .
H1 H 0.5859 0.8120 0.4269 0.087 Uiso 1 1 calc R U . . .
O2 O 0.7776(5) 0.8903(5) 0.2022(3) 0.0668(11) Uani 1 1 d . . . . .
I1 I 0.35252(4) 0.68348(4) 0.19669(3) 0.05641(18) 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
C8 N1 1.475(7) . ?
C8 C9 1.476(12) . ?
C8 C13 1.505(12) . ?
C8 C14 1.541(10) . ?
C9 C10 1.653(13) . ?
C9 H12A 0.9700 . ?
C9 H12B 0.9700 . ?
C10 C17 1.384(14) . ?
C10 C11 1.632(16) . ?
C10 H22 0.9800 . ?
C11 C12 1.477(14) . ?
C11 H24A 0.9700 . ?
C11 H24B 0.9700 . ?
C12 C16 1.453(14) . ?
C12 C13 1.591(13) . ?
C12 H23 0.9800 . ?
C13 H11A 0.9700 . ?
C13 H11B 0.9700 . ?
C14 C15 1.615(11) . ?
C14 H13A 0.9700 . ?
C14 H13B 0.9700 . ?
C15 C17 1.375(13) . ?
C15 C16 1.433(14) . ?
C15 H14 0.9800 . ?
C16 H21A 0.9700 . ?
C16 H21B 0.9700 . ?
C17 H20A 0.9700 . ?
C17 H20B 0.9700 . ?
C18 O2 1.406(8) . ?
C18 H15A 0.9600 . ?
C18 H15B 0.9600 . ?
C18 H15C 0.9600 . ?
C101 C102 1.380(7) . ?
C101 C103 1.382(7) . ?
C101 I1 2.092(5) . ?
C102 F2 1.341(6) . ?
C102 C103 1.378(7) 2_565 ?
C103 F1 1.340(6) . ?
C103 C102 1.377(7) 2_565 ?
N1 C7 1.278(7) . ?
C1 O1 1.310(6) . ?
C1 C6 1.408(7) . ?
C1 C2 1.420(7) . ?
C2 C3 1.360(8) . ?
C2 O2 1.370(6) . ?
C3 C4 1.407(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.356(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.409(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.443(7) . ?
C7 H8 0.9300 . ?
O1 H1 0.8200 . ?

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
N1 C8 C9 106.6(6) . . ?
N1 C8 C13 109.7(6) . . ?
C9 C8 C13 112.2(8) . . ?
N1 C8 C14 112.7(6) . . ?
C9 C8 C14 105.0(7) . . ?
C13 C8 C14 110.5(7) . . ?
C8 C9 C10 109.5(7) . . ?
C8 C9 H12A 109.8 . . ?
C10 C9 H12A 109.8 . . ?
C8 C9 H12B 109.8 . . ?
C10 C9 H12B 109.8 . . ?
H12A C9 H12B 108.2 . . ?
C17 C10 C11 112.9(10) . . ?
C17 C10 C9 107.1(9) . . ?
C11 C10 C9 97.2(8) . . ?
C17 C10 H22 112.9 . . ?
C11 C10 H22 112.8 . . ?
C9 C10 H22 112.9 . . ?
C12 C11 C10 114.7(10) . . ?
C12 C11 H24A 108.6 . . ?
C10 C11 H24A 108.6 . . ?
C12 C11 H24B 108.6 . . ?
C10 C11 H24B 108.6 . . ?
H24A C11 H24B 107.6 . . ?
C16 C12 C11 109.0(10) . . ?
C16 C12 C13 109.2(9) . . ?
C11 C12 C13 97.5(9) . . ?
C16 C12 H23 113.4 . . ?
C11 C12 H23 113.4 . . ?
C13 C12 H23 113.4 . . ?
C8 C13 C12 112.2(8) . . ?
C8 C13 H11A 109.2 . . ?
C12 C13 H11A 109.2 . . ?
C8 C13 H11B 109.2 . . ?
C12 C13 H11B 109.2 . . ?
H11A C13 H11B 107.9 . . ?
C8 C14 C15 108.3(6) . . ?
C8 C14 H13A 110.0 . . ?
C15 C14 H13A 110.0 . . ?
C8 C14 H13B 110.0 . . ?
C15 C14 H13B 110.0 . . ?
H13A C14 H13B 108.4 . . ?
C17 C15 C16 114.8(9) . . ?
C17 C15 C14 105.3(8) . . ?
C16 C15 C14 107.5(8) . . ?
C17 C15 H14 109.7 . . ?
C16 C15 H14 109.7 . . ?
C14 C15 H14 109.7 . . ?
C15 C16 C12 117.0(8) . . ?
C15 C16 H21A 108.0 . . ?
C12 C16 H21A 108.0 . . ?
C15 C16 H21B 108.0 . . ?
C12 C16 H21B 108.0 . . ?
H21A C16 H21B 107.3 . . ?
C15 C17 C10 115.8(9) . . ?
C15 C17 H20A 108.3 . . ?
C10 C17 H20A 108.3 . . ?
C15 C17 H20B 108.3 . . ?
C10 C17 H20B 108.3 . . ?
H20A C17 H20B 107.4 . . ?
O2 C18 H15A 109.5 . . ?
O2 C18 H15B 109.5 . . ?
H15A C18 H15B 109.5 . . ?
O2 C18 H15C 109.5 . . ?
H15A C18 H15C 109.5 . . ?
H15B C18 H15C 109.5 . . ?
C102 C101 C103 117.0(4) . . ?
C102 C101 I1 121.9(4) . . ?
C103 C101 I1 121.1(4) . . ?
F2 C102 C103 118.4(5) . 2_565 ?
F2 C102 C101 120.0(4) . . ?
C103 C102 C101 121.6(5) 2_565 . ?
F1 C103 C102 118.4(4) . 2_565 ?
F1 C103 C101 120.2(4) . . ?
C102 C103 C101 121.4(5) 2_565 . ?
C7 N1 C8 124.9(5) . . ?
O1 C1 C6 122.4(5) . . ?
O1 C1 C2 120.1(5) . . ?
C6 C1 C2 117.5(5) . . ?
C3 C2 O2 125.6(5) . . ?
C3 C2 C1 121.1(5) . . ?
O2 C2 C1 113.3(5) . . ?
C2 C3 C4 120.6(5) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.8(5) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 120.3(5) . . ?
C1 C6 C7 119.5(5) . . ?
C5 C6 C7 120.2(5) . . ?
N1 C7 C6 121.6(5) . . ?
N1 C7 H8 119.2 . . ?
C6 C7 H8 119.2 . . ?
C1 O1 H1 109.5 . . ?
C2 O2 C18 117.5(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C8 C9 C10 -179.5(7) . . . . ?
C13 C8 C9 C10 60.4(10) . . . . ?
C14 C8 C9 C10 -59.7(9) . . . . ?
C8 C9 C10 C17 58.2(11) . . . . ?
C8 C9 C10 C11 -58.5(10) . . . . ?
C17 C10 C11 C12 -38.8(13) . . . . ?
C9 C10 C11 C12 73.2(11) . . . . ?
C10 C11 C12 C16 39.7(13) . . . . ?
C10 C11 C12 C13 -73.5(11) . . . . ?
N1 C8 C13 C12 179.3(7) . . . . ?
C9 C8 C13 C12 -62.3(10) . . . . ?
C14 C8 C13 C12 54.4(10) . . . . ?
C16 C12 C13 C8 -50.6(12) . . . . ?
C11 C12 C13 C8 62.5(11) . . . . ?
N1 C8 C14 C15 179.1(6) . . . . ?
C9 C8 C14 C15 63.4(9) . . . . ?
C13 C8 C14 C15 -57.8(9) . . . . ?
C8 C14 C15 C17 -63.9(10) . . . . ?
C8 C14 C15 C16 58.9(10) . . . . ?
C17 C15 C16 C12 55.6(13) . . . . ?
C14 C15 C16 C12 -61.1(12) . . . . ?
C11 C12 C16 C15 -48.9(13) . . . . ?
C13 C12 C16 C15 56.5(12) . . . . ?
C16 C15 C17 C10 -51.8(13) . . . . ?
C14 C15 C17 C10 66.2(12) . . . . ?
C11 C10 C17 C15 43.0(13) . . . . ?
C9 C10 C17 C15 -62.9(12) . . . . ?
C103 C101 C102 F2 -179.8(5) . . . . ?
I1 C101 C102 F2 1.4(7) . . . . ?
C103 C101 C102 C103 0.2(8) . . . 2_565 ?
I1 C101 C102 C103 -178.6(4) . . . 2_565 ?
C102 C101 C103 F1 -179.5(4) . . . . ?
I1 C101 C103 F1 -0.8(6) . . . . ?
C102 C101 C103 C102 -0.2(8) . . . 2_565 ?
I1 C101 C103 C102 178.6(4) . . . 2_565 ?
C9 C8 N1 C7 121.9(7) . . . . ?
C13 C8 N1 C7 -116.4(7) . . . . ?
C14 C8 N1 C7 7.2(9) . . . . ?
O1 C1 C2 C3 -178.9(5) . . . . ?
C6 C1 C2 C3 0.6(7) . . . . ?
O1 C1 C2 O2 1.0(7) . . . . ?
C6 C1 C2 O2 -179.5(5) . . . . ?
O2 C2 C3 C4 179.3(5) . . . . ?
C1 C2 C3 C4 -0.8(8) . . . . ?
C2 C3 C4 C5 -0.5(9) . . . . ?
C3 C4 C5 C6 2.0(10) . . . . ?
O1 C1 C6 C5 -179.7(5) . . . . ?
C2 C1 C6 C5 0.8(7) . . . . ?
O1 C1 C6 C7 -1.2(8) . . . . ?
C2 C1 C6 C7 179.3(5) . . . . ?
C4 C5 C6 C1 -2.1(9) . . . . ?
C4 C5 C6 C7 179.4(6) . . . . ?
C8 N1 C7 C6 179.0(6) . . . . ?
C1 C6 C7 N1 1.2(8) . . . . ?
C5 C6 C7 N1 179.6(5) . . . . ?
C3 C2 O2 C18 -3.2(9) . . . . ?
C1 C2 O2 C18 177.0(6) . . . . ?

_refine_diff_density_max         1.896
_refine_diff_density_min         -0.914
_refine_diff_density_rms         0.122


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Diethyl ether'
