# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_ilb2814_0m
_database_code_depnum_ccdc_archive 'CCDC 1478819'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2017-05-19 downloaded from the CCDC.
;
_audit_creation_date             2016-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
'1,2(bis-4-pyridyl)ethane fluorohydroquinone co-crystal'
_chemical_formula_moiety         'C6 H5 F1 O2, C12 H12 N2'
_chemical_formula_sum            'C18 H17 F N2 O2'
_chemical_formula_weight         312.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1689(13)
_cell_length_b                   9.2830(15)
_cell_length_c                   11.8655(16)
_cell_angle_alpha                95.669(10)
_cell_angle_beta                 91.769(11)
_cell_angle_gamma                107.117(13)
_cell_volume                     749.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2033
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.954
_cell_measurement_theta_min      3.751
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1080 before and 0.0716 after correction.
The Ratio of minimum to maximum transmission is 0.7600.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'co-crystallisation from solvent'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_Laue_measured_fraction_full 0.937
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7125
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        66.961
_diffrn_reflns_theta_max         66.961
_diffrn_reflns_theta_min         3.751
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1728
_reflns_number_total             2511
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2511
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0701
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1333P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1822
_refine_ls_wR_factor_ref         0.2093
_refine_special_details          
'Disorder of fluorine/hydrogen positions modelled'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Sof(F1B)=Sof(H14)=1-FVAR(1)
 Sof(F1A)=Sof(H18)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C16(H16), C18(H18), C1(H1), C2(H2), C4(H4), C5(H5), C9(H9),
 C10(H10), C11(H11), C12(H12), C15(H15)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O2(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
F1A F -0.5522(6) 0.3522(4) 0.2901(3) 0.0449(11) Uani 0.512(6) 1 d . . P A 1
F1B F -0.5174(6) 1.0822(5) 0.2230(3) 0.0483(13) Uani 0.488(6) 1 d . . P A 2
O1 O -0.6133(4) 0.6421(3) 0.32771(17) 0.0443(6) Uani 1 1 d . . . . .
H1A H -0.6515 0.5811 0.2686 0.066 Uiso 1 1 calc GR . . . .
O2 O -0.1618(4) 1.0464(3) 0.13594(17) 0.0425(6) Uani 1 1 d . . . . .
H2A H -0.1835 1.0579 0.2049 0.064 Uiso 1 1 calc GR . . . .
C13 C -0.5609(5) 0.5700(4) 0.4100(2) 0.0353(7) Uani 1 1 d . . . . .
C14 C -0.5262(4) 0.4292(3) 0.3917(2) 0.0362(7) Uani 1 1 d . . . . .
H14 H -0.5451 0.3785 0.3168 0.043 Uiso 0.488(6) 1 calc R . P A 2
C16 C -0.3308(5) 0.9825(3) -0.0451(2) 0.0377(7) Uani 1 1 d . . . . .
H16 H -0.2158 0.9702 -0.0771 0.045 Uiso 1 1 calc R . . . .
C17 C -0.3308(5) 1.0237(3) 0.0713(2) 0.0371(7) Uani 1 1 d . . . . .
C18 C -0.5016(5) 1.0402(3) 0.1134(2) 0.0383(7) Uani 1 1 d . . . . .
H18 H -0.5038 1.0683 0.1925 0.046 Uiso 0.512(6) 1 calc R . P A 1
N1 N 0.1611(4) 0.8891(3) 0.63797(19) 0.0370(6) Uani 1 1 d . . . . .
N2 N -0.2875(4) 0.4928(3) -0.11696(19) 0.0347(6) Uani 1 1 d . . . . .
C1 C 0.2470(5) 0.9829(3) 0.5627(2) 0.0366(7) Uani 1 1 d . . . . .
H1 H 0.3380 1.0778 0.5907 0.044 Uiso 1 1 calc R . . . .
C2 C 0.2096(5) 0.9484(4) 0.4469(2) 0.0359(7) Uani 1 1 d . . . . .
H2 H 0.2763 1.0178 0.3972 0.043 Uiso 1 1 calc R . . . .
C3 C 0.0737(4) 0.8114(3) 0.4029(2) 0.0331(7) Uani 1 1 d . . . . .
C4 C -0.0148(5) 0.7149(4) 0.4802(2) 0.0366(7) Uani 1 1 d . . . . .
H4 H -0.1079 0.6200 0.4546 0.044 Uiso 1 1 calc R . . . .
C5 C 0.0325(5) 0.7571(4) 0.5951(2) 0.0371(7) Uani 1 1 d . . . . .
H5 H -0.0296 0.6884 0.6465 0.044 Uiso 1 1 calc R . . . .
C6 C 0.0284(5) 0.7773(3) 0.2758(2) 0.0337(7) Uani 1 1 d . . . . .
H6A H -0.0231 0.8566 0.2490 0.040 Uiso 1 1 calc R . . . .
H6B H 0.1516 0.7827 0.2386 0.040 Uiso 1 1 calc R . . . .
C7 C -0.1178(5) 0.6236(4) 0.2391(2) 0.0381(7) Uani 1 1 d . . . . .
H7A H -0.0650 0.5451 0.2662 0.046 Uiso 1 1 calc R . . . .
H7B H -0.2395 0.6185 0.2779 0.046 Uiso 1 1 calc R . . . .
C8 C -0.1706(4) 0.5833(3) 0.1133(2) 0.0338(7) Uani 1 1 d . . . . .
C9 C -0.1291(5) 0.6860(4) 0.0342(2) 0.0376(7) Uani 1 1 d . . . . .
H9 H -0.0610 0.7896 0.0573 0.045 Uiso 1 1 calc R . . . .
C10 C -0.1873(5) 0.6371(4) -0.0789(2) 0.0374(7) Uani 1 1 d . . . . .
H10 H -0.1548 0.7090 -0.1323 0.045 Uiso 1 1 calc R . . . .
C11 C -0.3282(5) 0.3951(3) -0.0405(2) 0.0374(7) Uani 1 1 d . . . . .
H11 H -0.3988 0.2926 -0.0657 0.045 Uiso 1 1 calc R . . . .
C12 C -0.2738(5) 0.4338(4) 0.0733(2) 0.0377(7) Uani 1 1 d . . . . .
H12 H -0.3065 0.3589 0.1244 0.045 Uiso 1 1 calc R . . . .
C15 C -0.4656(5) 0.3608(3) 0.4781(2) 0.0360(7) Uani 1 1 d . . . . .
H15 H -0.4417 0.2658 0.4614 0.043 Uiso 1 1 calc R . . . .


_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
F1A C14 1.318(4) . ?
F1B C18 1.338(4) . ?
O1 C13 1.341(4) . ?
O2 C17 1.364(4) . ?
C13 C14 1.399(4) . ?
C13 C15 1.398(4) 2_466 ?
C14 C15 1.381(4) . ?
C16 C17 1.396(4) . ?
C16 C18 1.379(5) 2_475 ?
C17 C18 1.381(5) . ?
C18 C16 1.379(5) 2_475 ?
N1 C1 1.344(4) . ?
N1 C5 1.340(4) . ?
N2 C10 1.344(4) . ?
N2 C11 1.324(4) . ?
C1 C2 1.379(4) . ?
C2 C3 1.396(4) . ?
C3 C4 1.383(4) . ?
C3 C6 1.515(3) . ?
C4 C5 1.384(4) . ?
C6 C7 1.514(4) . ?
C7 C8 1.511(4) . ?
C8 C9 1.380(4) . ?
C8 C12 1.393(4) . ?
C9 C10 1.384(4) . ?
C11 C12 1.376(4) . ?
C15 C13 1.398(4) 2_466 ?

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
O1 C13 C14 124.3(3) . . ?
O1 C13 C15 119.0(3) . 2_466 ?
C15 C13 C14 116.7(3) 2_466 . ?
F1A C14 C13 121.7(3) . . ?
F1A C14 C15 115.7(3) . . ?
C15 C14 C13 122.6(3) . . ?
C18 C16 C17 119.7(3) 2_475 . ?
O2 C17 C16 118.0(3) . . ?
O2 C17 C18 124.2(3) . . ?
C18 C17 C16 117.8(3) . . ?
F1B C18 C16 114.5(3) . 2_475 ?
F1B C18 C17 123.0(3) . . ?
C16 C18 C17 122.5(3) 2_475 . ?
C5 N1 C1 116.5(2) . . ?
C11 N2 C10 116.8(2) . . ?
N1 C1 C2 123.3(3) . . ?
C1 C2 C3 119.9(3) . . ?
C2 C3 C6 119.4(3) . . ?
C4 C3 C2 116.8(3) . . ?
C4 C3 C6 123.8(3) . . ?
C3 C4 C5 119.8(3) . . ?
N1 C5 C4 123.7(3) . . ?
C7 C6 C3 114.1(3) . . ?
C8 C7 C6 116.7(3) . . ?
C9 C8 C7 124.4(3) . . ?
C9 C8 C12 116.9(3) . . ?
C12 C8 C7 118.7(3) . . ?
C8 C9 C10 119.6(3) . . ?
N2 C10 C9 123.2(3) . . ?
N2 C11 C12 123.7(3) . . ?
C11 C12 C8 119.8(3) . . ?
C14 C15 C13 120.7(3) . 2_466 ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2014-12-09
_olex2_date_sample_submission    2014-12-09
_olex2_submission_original_sample_id 
'1,2(bis-4-pyridyl)ethane fluorohydroquinone cocrx'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ilb2850_0m
_database_code_depnum_ccdc_archive 'CCDC 1478820'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2017-05-19 downloaded from the CCDC.
;
_audit_creation_date             2016-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
'1,2-Bis(4-pyridyl)ethane tetrafluorohydroquinone co-crystal'
_chemical_formula_moiety         'C12 H12 N2, C6 H2 F4 O2'
_chemical_formula_sum            'C18 H14 F4 N2 O2'
_chemical_formula_weight         366.31
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1939(4)
_cell_length_b                   7.4692(5)
_cell_length_c                   9.0672(6)
_cell_angle_alpha                86.863(5)
_cell_angle_beta                 75.722(5)
_cell_angle_gamma                71.755(4)
_cell_volume                     385.97(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1818
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.782
_cell_measurement_theta_min      2.318
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.0491 before and 0.0407 after correction.
The Ratio of minimum to maximum transmission is 0.9347.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             188
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'co-crystallisation from solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6725
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.562
_diffrn_reflns_theta_min         2.318
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1373
_reflns_number_total             1778
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1778
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.1800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0955
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 -0.2009(2) -0.03074(18) 0.75576(15) 0.0198(3) Uani 1 1 d . . . . .
C1 C -0.1501(3) -0.1144(2) 0.88200(19) 0.0211(4) Uani 1 1 d . . . . .
H1 H -0.0284 -0.0913 0.9168 0.025 Uiso 1 1 calc R . . . .
C2 C -0.2647(3) -0.2336(2) 0.96558(19) 0.0211(4) Uani 1 1 d . . . . .
H2 H -0.2228 -0.2885 1.0556 0.025 Uiso 1 1 calc R . . . .
C3 C -0.4410(3) -0.2717(2) 0.91646(18) 0.0193(4) Uani 1 1 d . . . . .
C4 C -0.4903(3) -0.1888(2) 0.78211(19) 0.0215(4) Uani 1 1 d . . . . .
H4 H -0.6062 -0.2142 0.7422 0.026 Uiso 1 1 calc R . . . .
C5 C -0.3700(3) -0.0697(2) 0.70723(19) 0.0212(4) Uani 1 1 d . . . . .
H5 H -0.4086 -0.0125 0.6171 0.025 Uiso 1 1 calc R . . . .
C6 C -0.5738(3) -0.3966(2) 1.0068(2) 0.0243(4) Uani 1 1 d . . . . .
H6A H -0.7161 -0.3820 0.9701 0.029 Uiso 1 1 calc R . . . .
H6B H -0.6243 -0.3556 1.1153 0.029 Uiso 1 1 calc R . . . .
F1 F -0.23682(17) 0.25043(13) 0.49357(11) 0.0227(2) Uani 1 1 d . . . . .
F2 F 0.29233(17) 0.45208(14) 0.68914(11) 0.0244(3) Uani 1 1 d . . . . .
O1 O 0.0687(2) 0.19114(16) 0.68806(13) 0.0221(3) Uani 1 1 d . . . . .
H1A H -0.0274 0.1329 0.6883 0.033 Uiso 1 1 calc GR . . . .
C7 C -0.1190(3) 0.3746(2) 0.49932(17) 0.0174(3) Uani 1 1 d . . . . .
C8 C 0.0284(3) 0.3418(2) 0.59742(17) 0.0167(3) Uani 1 1 d . . . . .
C9 C 0.1467(3) 0.4731(2) 0.59548(17) 0.0169(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
N1 C1 1.333(2) . ?
N1 C5 1.345(2) . ?
C1 C2 1.388(2) . ?
C2 C3 1.386(2) . ?
C3 C4 1.394(2) . ?
C3 C6 1.511(2) . ?
C4 C5 1.381(2) . ?
C6 C6 1.523(3) 2_447 ?
F1 C7 1.3580(17) . ?
F2 C9 1.3543(17) . ?
O1 C8 1.3521(18) . ?
C7 C8 1.386(2) . ?
C7 C9 1.380(2) 2_566 ?
C8 C9 1.393(2) . ?
C9 C7 1.380(2) 2_566 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 116.80(13) . . ?
N1 C1 C2 123.75(15) . . ?
C3 C2 C1 119.34(15) . . ?
C2 C3 C4 117.15(14) . . ?
C2 C3 C6 120.75(15) . . ?
C4 C3 C6 122.10(15) . . ?
C5 C4 C3 119.72(15) . . ?
N1 C5 C4 123.20(15) . . ?
C3 C6 C6 112.11(17) . 2_447 ?
F1 C7 C8 118.93(13) . . ?
F1 C7 C9 118.62(14) . 2_566 ?
C9 C7 C8 122.43(14) 2_566 . ?
O1 C8 C7 124.73(14) . . ?
O1 C8 C9 119.39(14) . . ?
C7 C8 C9 115.83(14) . . ?
F2 C9 C7 118.81(13) . 2_566 ?
F2 C9 C8 119.46(13) . . ?
C7 C9 C8 121.73(14) 2_566 . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-01-12
_olex2_submission_original_sample_id ccrx17HB
_olex2_submission_special_instructions 'No special instructions were received'
