# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_eze5t
_database_code_depnum_ccdc_archive 'CCDC 2098283'
loop_
_audit_author_name
_audit_author_address
'Hemant P. Yennawar'
;The Pennsylvania State University
United States of America
;
_audit_update_record             
;
2021-07-21 deposited with the CCDC.	2022-02-02 downloaded from the CCDC.
;
_audit_creation_date             2021-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ArOH:ArFCHO
_chemical_name_systematic        Phenol:Pentafluorobenzaldehyde
_chemical_formula_moiety         'C7 H F5 O, C6 H6 O'
_chemical_formula_sum            'C13 H7 F5 O2'
_chemical_formula_weight         290.19
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.3270(13)
_cell_length_b                   26.441(5)
_cell_length_c                   7.0232(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.01(3)
_cell_angle_gamma                90.00
_cell_volume                     1170.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3209
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      28.215
_cell_measurement_theta_min      2.711
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.9
_exptl_absorpt_correction_T_min  0.211737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS V2.05 (BRUKER, 2001) was used for absorption correction.
R(int) was 0.1111 before and 0.0458 after correction.
The Ratio of minimum to maximum transmission is 0.2117.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 The data collection nominally covered a full sphere of reciprocal space by
 a combination of 4 sets of ω scans each set at different φ and/or
 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω.
 The crystal to detector distance was 5.82 cm.
;
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_av_unetI/netI     0.1164
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5773
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.55
_diffrn_reflns_theta_min         1.54
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean 8.34
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           32.0
_diffrn_source_power             1.6
_diffrn_source_voltage           50.0
_reflns_number_gt                1376
_reflns_number_total             2709
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V6.36A (BRUKER, 2001)'
_computing_data_collection       'SMART V5.634 (Bruker Inc., 2001)'
_computing_data_reduction        'SAINT V6.36A (BRUKER, 2001)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2709
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1479
_refine_ls_R_factor_gt           0.0796
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1880
_refine_ls_wR_factor_ref         0.2305
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 O2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F 1.0256(3) 0.19012(8) 0.8099(3) 0.0402(6) Uani 1 d . . .
F2 F 1.1051(4) 0.09082(8) 0.8254(4) 0.0423(7) Uani 1 d . . .
F3 F 0.8009(4) 0.02378(8) 0.7012(4) 0.0489(7) Uani 1 d . . .
F4 F 0.4115(4) 0.05601(8) 0.5614(4) 0.0453(7) Uani 1 d . . .
F5 F 0.3289(3) 0.15570(8) 0.5403(3) 0.0414(7) Uani 1 d . . .
O1 O 0.7462(5) 0.26486(10) 0.6867(5) 0.0486(9) Uani 1 d . . .
C1 C 0.6737(6) 0.17628(13) 0.6739(6) 0.0280(9) Uani 1 d . . .
C2 C 0.8706(6) 0.15838(13) 0.7464(6) 0.0290(9) Uani 1 d . . .
C3 C 0.9152(6) 0.10757(14) 0.7555(6) 0.0295(9) Uani 1 d . . .
C4 C 0.7591(7) 0.07340(13) 0.6937(6) 0.0338(10) Uani 1 d . . .
C5 C 0.5630(6) 0.08944(14) 0.6213(6) 0.0312(9) Uani 1 d . . .
C6 C 0.5217(6) 0.14096(14) 0.6120(6) 0.0304(9) Uani 1 d . . .
C7 C 0.6198(7) 0.23068(14) 0.6597(6) 0.0374(11) Uani 1 d . . .
H7 H 0.4786 0.2392 0.6276 0.045 Uiso 1 calc . . R
O2 O 0.6711(5) 0.20639(10) 0.1967(5) 0.0454(8) Uani 1 d . . .
H2 H 0.5487 0.2143 0.1620 0.068 Uiso 1 d . . R
C8 C 0.6898(6) 0.15453(14) 0.1891(6) 0.0310(9) Uani 1 d . . .
C9 C 0.5199(6) 0.12335(15) 0.1337(5) 0.0324(9) Uani 1 d . . .
H9 H 0.3869 0.1369 0.0976 0.039 Uiso 1 calc . . R
C10 C 0.5516(7) 0.07166(15) 0.1330(6) 0.0373(10) Uani 1 d . . .
H10 H 0.4384 0.0503 0.0965 0.045 Uiso 1 calc . . R
C11 C 0.7486(7) 0.05125(16) 0.1855(6) 0.0392(11) Uani 1 d . . .
H11 H 0.7680 0.0164 0.1847 0.047 Uiso 1 calc . . R
C12 C 0.9162(7) 0.08273(14) 0.2391(6) 0.0375(10) Uani 1 d . . .
H12 H 1.0491 0.0691 0.2751 0.045 Uiso 1 calc . . R
C13 C 0.8882(6) 0.13503(14) 0.2398(6) 0.0342(10) Uani 1 d . . .
H13 H 1.0020 0.1564 0.2740 0.041 Uiso 1 calc . . R

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0361(13) 0.0285(12) 0.0540(17) -0.0065(11) -0.0066(11) -0.0027(10)
F2 0.0369(14) 0.0369(13) 0.0521(17) 0.0039(11) -0.0014(11) 0.0099(11)
F3 0.0648(17) 0.0186(12) 0.0629(18) 0.0017(11) 0.0043(14) 0.0060(11)
F4 0.0456(14) 0.0316(13) 0.0583(18) -0.0054(12) 0.0025(12) -0.0161(11)
F5 0.0285(13) 0.0394(13) 0.0550(17) 0.0027(12) -0.0039(11) 0.0018(10)
O1 0.0442(18) 0.0245(15) 0.076(2) -0.0033(15) -0.0028(17) -0.0026(13)
C1 0.034(2) 0.0193(18) 0.031(2) 0.0000(16) 0.0028(17) -0.0023(15)
C2 0.030(2) 0.0257(19) 0.031(2) -0.0033(17) -0.0004(17) -0.0043(16)
C3 0.027(2) 0.0257(19) 0.036(2) 0.0000(17) 0.0016(18) 0.0069(16)
C4 0.049(3) 0.0156(17) 0.038(3) 0.0000(17) 0.008(2) 0.0026(17)
C5 0.036(2) 0.0226(19) 0.035(3) -0.0009(16) 0.0024(18) -0.0083(16)
C6 0.028(2) 0.029(2) 0.034(2) 0.0047(17) 0.0038(18) -0.0025(16)
C7 0.036(2) 0.021(2) 0.055(3) -0.0035(18) 0.001(2) 0.0018(17)
O2 0.0436(17) 0.0222(14) 0.071(2) -0.0014(14) 0.0068(16) 0.0013(12)
C8 0.035(2) 0.026(2) 0.032(2) 0.0026(17) 0.0067(18) -0.0003(17)
C9 0.033(2) 0.037(2) 0.027(2) -0.0007(18) 0.0041(17) -0.0008(18)
C10 0.043(2) 0.035(2) 0.034(3) -0.0022(19) 0.004(2) -0.0046(19)
C11 0.049(3) 0.030(2) 0.039(3) 0.0028(19) 0.006(2) 0.0031(19)
C12 0.039(2) 0.032(2) 0.042(3) 0.0041(19) 0.007(2) 0.0026(18)
C13 0.035(2) 0.033(2) 0.035(2) 0.0007(18) 0.0055(19) 0.0005(18)

_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 C2 1.337(4) . ?
F2 C3 1.333(4) . ?
F3 C4 1.338(4) . ?
F4 C5 1.345(4) . ?
F5 C6 1.337(4) . ?
O1 C7 1.211(4) . ?
C1 C2 1.387(5) . ?
C1 C6 1.383(5) . ?
C1 C7 1.480(5) . ?
C2 C3 1.373(5) . ?
C3 C4 1.381(5) . ?
C4 C5 1.366(6) . ?
C5 C6 1.387(5) . ?
C7 H7 0.9300 . ?
O2 H2 0.8185 . ?
O2 C8 1.378(4) . ?
C8 C9 1.383(5) . ?
C8 C13 1.375(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.394(5) . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C7 123.4(3) . . ?
C6 C1 C2 117.5(3) . . ?
C6 C1 C7 119.1(3) . . ?
F1 C2 C1 121.1(3) . . ?
F1 C2 C3 117.2(3) . . ?
C3 C2 C1 121.7(3) . . ?
F2 C3 C2 121.1(3) . . ?
F2 C3 C4 119.7(3) . . ?
C2 C3 C4 119.1(3) . . ?
F3 C4 C3 119.7(4) . . ?
F3 C4 C5 119.3(4) . . ?
C5 C4 C3 121.0(3) . . ?
F4 C5 C4 120.8(3) . . ?
F4 C5 C6 120.3(4) . . ?
C4 C5 C6 118.9(4) . . ?
F5 C6 C1 120.5(3) . . ?
F5 C6 C5 117.8(3) . . ?
C1 C6 C5 121.7(4) . . ?
O1 C7 C1 124.8(4) . . ?
O1 C7 H7 117.6 . . ?
C1 C7 H7 117.6 . . ?
C8 O2 H2 108.9 . . ?
O2 C8 C9 122.5(4) . . ?
C13 C8 O2 116.3(4) . . ?
C13 C8 C9 121.2(4) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.8(4) . . ?
C10 C9 H9 120.6 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(4) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.6(4) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(4) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 119.0(4) . . ?
C8 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?

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 C2 C3 F2 0.2(6) . . . . ?
F1 C2 C3 C4 179.2(3) . . . . ?
F2 C3 C4 F3 -1.3(6) . . . . ?
F2 C3 C4 C5 -180.0(4) . . . . ?
F3 C4 C5 F4 1.3(6) . . . . ?
F3 C4 C5 C6 -179.3(4) . . . . ?
F4 C5 C6 F5 -0.7(6) . . . . ?
F4 C5 C6 C1 179.5(3) . . . . ?
C1 C2 C3 F2 180.0(3) . . . . ?
C1 C2 C3 C4 -1.1(6) . . . . ?
C2 C1 C6 F5 -179.9(3) . . . . ?
C2 C1 C6 C5 -0.1(6) . . . . ?
C2 C1 C7 O1 9.5(7) . . . . ?
C2 C3 C4 F3 179.8(4) . . . . ?
C2 C3 C4 C5 1.0(6) . . . . ?
C3 C4 C5 F4 -180.0(4) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
C4 C5 C6 F5 179.9(3) . . . . ?
C4 C5 C6 C1 0.0(7) . . . . ?
C6 C1 C2 F1 -179.7(4) . . . . ?
C6 C1 C2 C3 0.6(6) . . . . ?
C6 C1 C7 O1 -170.4(4) . . . . ?
C7 C1 C2 F1 0.4(6) . . . . ?
C7 C1 C2 C3 -179.3(4) . . . . ?
C7 C1 C6 F5 0.0(6) . . . . ?
C7 C1 C6 C5 179.8(4) . . . . ?
O2 C8 C9 C10 -179.0(3) . . . . ?
O2 C8 C13 C12 178.6(4) . . . . ?
C8 C9 C10 C11 -0.3(6) . . . . ?
C9 C8 C13 C12 -1.5(6) . . . . ?
C9 C10 C11 C12 -0.1(7) . . . . ?
C10 C11 C12 C13 -0.3(6) . . . . ?
C11 C12 C13 C8 1.1(6) . . . . ?
C13 C8 C9 C10 1.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'solvent evaporation'
####################################################################### 
# 
# 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_eze3s
_database_code_depnum_ccdc_archive 'CCDC 2098284'
loop_
_audit_author_name
_audit_author_address
'Hemant P. Yennawar'
;The Pennsylvania State University
United States of America
;
_audit_update_record             
;
2021-07-21 deposited with the CCDC.	2022-02-02 downloaded from the CCDC.
;
_audit_creation_date             2021-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ArCHO:ArFOH
_chemical_name_systematic        Benzaldehyde:Pentafluorophenol
_chemical_formula_moiety         'C6 H F5 O, C7 H6 O'
_chemical_formula_sum            'C13 H7 F5 O2'
_chemical_formula_weight         290.19
_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'
O O 0.0106 0.0060 '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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   5.9872(15)
_cell_length_b                   7.934(2)
_cell_length_c                   13.242(3)
_cell_angle_alpha                105.378(4)
_cell_angle_beta                 99.982(5)
_cell_angle_gamma                94.446(4)
_cell_volume                     592.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2293
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      28.268
_cell_measurement_theta_min      2.686
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  0.9
_exptl_absorpt_correction_T_min  0.763967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS V2.05 (BRUKER, 2001) was used for absorption correction.
R(int) was 0.0559 before and 0.0168 after correction.
The Ratio of minimum to maximum transmission is 0.7640.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 The data collection nominally covered a full sphere of reciprocal space by
 a combination of 4 sets of ω scans each set at different φ and/or
 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω.
 The crystal to detector distance was 5.82 cm.
;
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4715
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.63
_diffrn_ambient_temperature      183.15
_diffrn_detector_area_resol_mean 8.34
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           32.0
_diffrn_source_power             1.6
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2166
_reflns_number_total             2702
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V6.36A (BRUKER, 2001)'
_computing_data_collection       'SMART V5.634 (Bruker Inc., 2001)'
_computing_data_reduction        'SAINT V6.36A (BRUKER, 2001)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2702
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0773P)²+0.0529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1360
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.4062(2) 0.35579(18) 0.65740(11) 0.0370(3) Uani 1 d . . .
C2 C 0.2799(2) 0.28641(18) 0.71850(11) 0.0350(3) Uani 1 d . . .
C3 C 0.3851(2) 0.30338(17) 0.82368(10) 0.0350(3) Uani 1 d . . .
C4 C 0.6063(2) 0.38335(18) 0.86456(10) 0.0381(3) Uani 1 d . . .
C5 C 0.7289(2) 0.45143(18) 0.80215(11) 0.0383(3) Uani 1 d . . .
C6 C 0.6282(2) 0.43685(18) 0.69799(11) 0.0377(3) Uani 1 d . . .
F1 F 0.30862(16) 0.34456(14) 0.55595(7) 0.0531(3) Uani 1 d . . .
F3 F 0.27118(15) 0.23656(12) 0.88581(7) 0.0473(3) Uani 1 d . . .
F4 F 0.70482(16) 0.39524(13) 0.96572(7) 0.0516(3) Uani 1 d . . .
F5 F 0.94347(15) 0.53166(12) 0.84253(8) 0.0509(3) Uani 1 d . . .
F6 F 0.74344(16) 0.50491(13) 0.63679(8) 0.0517(3) Uani 1 d . . .
O1 O 0.06443(17) 0.20301(14) 0.68331(9) 0.0438(3) Uani 1 d . . .
H1 H 0.008(4) 0.200(3) 0.621(2) 0.081(7) Uiso 1 d . . .
C7 C 0.3078(3) 0.7920(2) 0.76848(13) 0.0448(4) Uani 1 d . . .
H7 H 0.1629 0.7346 0.7629 0.054 Uiso 1 calc . . R
C8 C 0.4686(3) 0.8262(2) 0.86289(13) 0.0506(4) Uani 1 d . . .
H8 H 0.4322 0.7935 0.9211 0.061 Uiso 1 calc . . R
C9 C 0.6835(3) 0.9094(2) 0.86878(13) 0.0523(4) Uani 1 d . . .
H9 H 0.7927 0.9319 0.9315 0.063 Uiso 1 calc . . R
C10 C 0.7397(3) 0.9602(2) 0.78320(13) 0.0474(4) Uani 1 d . . .
H10 H 0.8853 1.0167 0.7888 0.057 Uiso 1 calc . . R
C11 C 0.5791(2) 0.92681(18) 0.68931(12) 0.0412(3) Uani 1 d . . .
H11 H 0.6159 0.9601 0.6313 0.049 Uiso 1 calc . . R
C12 C 0.3623(2) 0.84312(17) 0.68247(11) 0.0371(3) Uani 1 d . . .
C13 C 0.1848(3) 0.8091(2) 0.58522(13) 0.0470(4) Uani 1 d . . .
H13 H 0.0456 0.7471 0.5840 0.056 Uiso 1 calc . . R
O2 O 0.2036(2) 0.85439(16) 0.50705(9) 0.0533(3) Uani 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0361(7) 0.0440(7) 0.0300(6) 0.0117(5) 0.0025(5) 0.0042(6)
C2 0.0296(7) 0.0396(7) 0.0333(7) 0.0083(5) 0.0028(5) 0.0045(5)
C3 0.0356(7) 0.0382(7) 0.0325(7) 0.0131(5) 0.0064(5) 0.0026(5)
C4 0.0380(7) 0.0406(7) 0.0313(7) 0.0083(5) -0.0011(5) 0.0035(6)
C5 0.0296(7) 0.0406(7) 0.0403(8) 0.0084(6) 0.0016(5) 0.0005(5)
C6 0.0368(7) 0.0411(7) 0.0374(7) 0.0136(6) 0.0102(6) 0.0037(6)
F1 0.0478(5) 0.0779(7) 0.0332(5) 0.0235(4) -0.0006(4) -0.0022(5)
F3 0.0458(5) 0.0587(5) 0.0378(5) 0.0195(4) 0.0064(4) -0.0064(4)
F4 0.0485(5) 0.0658(6) 0.0341(5) 0.0165(4) -0.0069(4) -0.0055(4)
F5 0.0339(5) 0.0589(5) 0.0525(5) 0.0143(4) -0.0023(4) -0.0089(4)
F6 0.0473(5) 0.0633(6) 0.0479(5) 0.0226(4) 0.0133(4) -0.0047(4)
O1 0.0326(6) 0.0585(6) 0.0372(6) 0.0153(5) 0.0006(4) -0.0045(4)
C7 0.0404(8) 0.0464(8) 0.0506(9) 0.0193(7) 0.0099(6) 0.0020(6)
C8 0.0614(11) 0.0541(9) 0.0419(8) 0.0208(7) 0.0126(7) 0.0109(8)
C9 0.0510(10) 0.0551(9) 0.0434(9) 0.0115(7) -0.0074(7) 0.0089(7)
C10 0.0346(8) 0.0490(8) 0.0543(9) 0.0143(7) 0.0006(6) -0.0002(6)
C11 0.0385(8) 0.0424(7) 0.0419(8) 0.0122(6) 0.0068(6) 0.0030(6)
C12 0.0343(7) 0.0372(7) 0.0371(7) 0.0099(5) 0.0021(5) 0.0033(5)
C13 0.0381(8) 0.0504(8) 0.0466(8) 0.0113(7) -0.0003(6) -0.0011(6)
O2 0.0496(7) 0.0664(7) 0.0390(6) 0.0170(5) -0.0038(5) 0.0002(5)

_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 1.384(2) . ?
C1 C6 1.380(2) . ?
C1 F1 1.3456(16) . ?
C2 C3 1.3922(18) . ?
C2 O1 1.3471(17) . ?
C3 C4 1.374(2) . ?
C3 F3 1.3391(16) . ?
C4 C5 1.378(2) . ?
C4 F4 1.3423(15) . ?
C5 C6 1.377(2) . ?
C5 F5 1.3404(16) . ?
C6 F6 1.3390(17) . ?
O1 H1 0.83(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(2) . ?
C7 C12 1.386(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(2) . ?
C12 C13 1.469(2) . ?
C13 H13 0.9300 . ?
C13 O2 1.202(2) . ?

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
C6 C1 C2 121.77(13) . . ?
F1 C1 C2 118.81(13) . . ?
F1 C1 C6 119.41(13) . . ?
C1 C2 C3 117.17(13) . . ?
O1 C2 C1 124.78(12) . . ?
O1 C2 C3 118.05(13) . . ?
C4 C3 C2 121.40(13) . . ?
F3 C3 C2 119.53(12) . . ?
F3 C3 C4 119.05(12) . . ?
C3 C4 C5 120.39(13) . . ?
F4 C4 C3 120.13(14) . . ?
F4 C4 C5 119.48(13) . . ?
C6 C5 C4 119.28(13) . . ?
F5 C5 C4 120.37(13) . . ?
F5 C5 C6 120.35(14) . . ?
C5 C6 C1 119.98(14) . . ?
F6 C6 C1 119.94(13) . . ?
F6 C6 C5 120.06(13) . . ?
C2 O1 H1 114.2(16) . . ?
C8 C7 H7 119.8 . . ?
C12 C7 H7 119.8 . . ?
C12 C7 C8 120.30(15) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.79(15) . . ?
C9 C8 H8 120.6 . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.31(14) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.85(15) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.35(15) . . ?
C12 C11 H11 120.3 . . ?
C7 C12 C11 120.39(13) . . ?
C7 C12 C13 118.49(14) . . ?
C11 C12 C13 121.11(14) . . ?
C12 C13 H13 117.1 . . ?
O2 C13 C12 125.76(15) . . ?
O2 C13 H13 117.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.83(2) 1.86(2) 2.6482(15) 159(2) 2_566

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
C1 C2 C3 C4 -0.9(2) . . . . ?
C1 C2 C3 F3 -179.19(12) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
C2 C1 C6 F6 -178.90(12) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C2 C3 C4 F4 -178.87(12) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C3 C4 C5 F5 179.04(12) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C4 C5 C6 F6 178.86(12) . . . . ?
C6 C1 C2 C3 0.7(2) . . . . ?
C6 C1 C2 O1 -178.75(13) . . . . ?
F1 C1 C2 C3 -178.84(12) . . . . ?
F1 C1 C2 O1 1.7(2) . . . . ?
F1 C1 C6 C5 179.07(12) . . . . ?
F1 C1 C6 F6 0.6(2) . . . . ?
F3 C3 C4 C5 179.20(12) . . . . ?
F3 C3 C4 F4 -0.6(2) . . . . ?
F4 C4 C5 C6 179.14(12) . . . . ?
F4 C4 C5 F5 -1.2(2) . . . . ?
F5 C5 C6 C1 -179.28(12) . . . . ?
F5 C5 C6 F6 -0.8(2) . . . . ?
O1 C2 C3 C4 178.56(12) . . . . ?
O1 C2 C3 F3 0.3(2) . . . . ?
C7 C8 C9 C10 0.6(2) . . . . ?
C7 C12 C13 O2 175.75(15) . . . . ?
C8 C7 C12 C11 0.9(2) . . . . ?
C8 C7 C12 C13 -178.20(13) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C10 C11 C12 C7 -0.6(2) . . . . ?
C10 C11 C12 C13 178.46(13) . . . . ?
C11 C12 C13 O2 -3.3(2) . . . . ?
C12 C7 C8 C9 -0.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'solvent evaporation'
