# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

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

data_Y239
_database_code_depnum_ccdc_archive 'CCDC 1838805'
_audit_update_record             
;
2018-04-23 deposited with the CCDC.
2018-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2,3,5,6-tetrafluoro-4-[4-[(4-methoxyphenyl)ethynyl]phenylethynyl]anisole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H14 F4 O2'
_chemical_formula_weight         410.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   15.9200(13)
_cell_length_b                   5.8083(4)
_cell_length_c                   20.4496(14)
_cell_angle_alpha                90
_cell_angle_beta                 100.147(7)
_cell_angle_gamma                90
_cell_volume                     1861.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5676
_cell_measurement_theta_min      3.5140
_cell_measurement_theta_max      32.4380

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.119
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82604
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15613
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.599
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3419
_reflns_number_gt                2895
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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)+(0.0322P)²+3.6701P] 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         3419
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1519
_refine_ls_wR_factor_gt          0.1468
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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 0.0962(2) -0.2512(7) 0.52471(19) 0.0558(10) Uani 1 1 d . . . . .
H1 H 0.1060 -0.3965 0.5029 0.084 Uiso 1 1 calc R U . . .
H2 H 0.0388 -0.2518 0.5358 0.084 Uiso 1 1 calc R U . . .
H3 H 0.1385 -0.2341 0.5654 0.084 Uiso 1 1 calc R U . . .
C2 C 0.18188(17) -0.0226(5) 0.46423(14) 0.0350(7) Uani 1 1 d . . . . .
C3 C 0.18809(19) 0.1821(6) 0.43080(16) 0.0413(7) Uani 1 1 d . . . . .
H4 H 0.1398 0.2803 0.4207 0.050 Uiso 1 1 calc R U . . .
C4 C 0.26340(19) 0.2440(5) 0.41218(15) 0.0394(7) Uani 1 1 d . . . . .
H5 H 0.2668 0.3848 0.3892 0.047 Uiso 1 1 calc R U . . .
C5 C 0.33533(18) 0.1030(5) 0.42658(14) 0.0339(6) Uani 1 1 d . . . . .
C6 C 0.32737(18) -0.1040(5) 0.45918(14) 0.0351(7) Uani 1 1 d . . . . .
H6 H 0.3752 -0.2041 0.4685 0.042 Uiso 1 1 calc R U . . .
C7 C 0.25167(18) -0.1676(5) 0.47841(14) 0.0368(7) Uani 1 1 d . . . . .
H7 H 0.2476 -0.3089 0.5010 0.044 Uiso 1 1 calc R U . . .
C8 C 0.41561(18) 0.1802(6) 0.41200(15) 0.0376(7) Uani 1 1 d . . . . .
C9 C 0.48083(19) 0.2581(6) 0.40070(15) 0.0390(7) Uani 1 1 d . . . . .
C10 C 0.55853(17) 0.3639(5) 0.38978(14) 0.0331(6) Uani 1 1 d . . . . .
C11 C 0.58228(19) 0.5781(6) 0.41802(15) 0.0389(7) Uani 1 1 d . . . . .
H8 H 0.5467 0.6525 0.4442 0.047 Uiso 1 1 calc R U . . .
C12 C 0.65711(18) 0.6835(5) 0.40833(14) 0.0361(7) Uani 1 1 d . . . . .
H9 H 0.6727 0.8288 0.4282 0.043 Uiso 1 1 calc R U . . .
C13 C 0.70935(17) 0.5775(5) 0.36974(14) 0.0328(6) Uani 1 1 d . . . . .
C14 C 0.68607(18) 0.3631(5) 0.34171(15) 0.0365(7) Uani 1 1 d . . . . .
H10 H 0.7218 0.2885 0.3157 0.044 Uiso 1 1 calc R U . . .
C15 C 0.61157(18) 0.2583(5) 0.35148(15) 0.0364(7) Uani 1 1 d . . . . .
H11 H 0.5963 0.1125 0.3319 0.044 Uiso 1 1 calc R U . . .
C16 C 0.78601(18) 0.6885(6) 0.35816(15) 0.0374(7) Uani 1 1 d . . . . .
C17 C 0.84930(18) 0.7759(5) 0.34629(15) 0.0365(7) Uani 1 1 d . . . . .
C18 C 0.92634(17) 0.8599(5) 0.32814(13) 0.0308(6) Uani 1 1 d . . . . .
C19 C 0.93109(17) 1.0659(5) 0.29476(14) 0.0319(6) Uani 1 1 d . . . . .
C20 C 1.00322(18) 1.1346(5) 0.27146(14) 0.0328(6) Uani 1 1 d . . . . .
C21 C 1.07601(17) 0.9997(5) 0.28076(14) 0.0344(7) Uani 1 1 d . . . . .
C22 C 1.07200(17) 0.7959(5) 0.31573(15) 0.0353(7) Uani 1 1 d . . . . .
C23 C 1.00078(18) 0.7307(5) 0.33880(14) 0.0335(6) Uani 1 1 d . . . . .
C24 C 1.1564(2) 1.2146(7) 0.21179(19) 0.0582(10) Uani 1 1 d . . . . .
H12 H 1.1121 1.1868 0.1728 0.087 Uiso 1 1 calc R U . . .
H13 H 1.2127 1.2064 0.1988 0.087 Uiso 1 1 calc R U . . .
H14 H 1.1483 1.3676 0.2299 0.087 Uiso 1 1 calc R U . . .
O1 O 0.10381(13) -0.0635(5) 0.48094(11) 0.0505(6) Uani 1 1 d . . . . .
O2 O 1.15062(13) 1.0449(5) 0.26080(12) 0.0548(7) Uani 1 1 d . . . . .
F1 F 0.86290(11) 1.2050(3) 0.28337(9) 0.0458(5) Uani 1 1 d . . . . .
F2 F 1.00009(12) 1.3383(3) 0.23955(9) 0.0479(5) Uani 1 1 d . . . . .
F3 F 1.00204(12) 0.5298(3) 0.37173(9) 0.0472(5) Uani 1 1 d . . . . .
F4 F 1.14132(11) 0.6594(4) 0.32695(10) 0.0532(5) 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 O1 1.429(4) . ?
C1 H1 0.9800 . ?
C1 H2 0.9800 . ?
C1 H3 0.9800 . ?
C2 O1 1.367(3) . ?
C2 C3 1.384(4) . ?
C2 C7 1.384(4) . ?
C3 C4 1.368(4) . ?
C3 H4 0.9500 . ?
C4 C5 1.396(4) . ?
C4 H5 0.9500 . ?
C5 C6 1.391(4) . ?
C5 C8 1.435(4) . ?
C6 C7 1.382(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.192(4) . ?
C9 C10 1.433(4) . ?
C10 C15 1.391(4) . ?
C10 C11 1.395(4) . ?
C11 C12 1.384(4) . ?
C11 H8 0.9500 . ?
C12 C13 1.387(4) . ?
C12 H9 0.9500 . ?
C13 C14 1.394(4) . ?
C13 C16 1.436(4) . ?
C14 C15 1.379(4) . ?
C14 H10 0.9500 . ?
C15 H11 0.9500 . ?
C16 C17 1.191(4) . ?
C17 C18 1.428(4) . ?
C18 C19 1.387(4) . ?
C18 C23 1.387(4) . ?
C19 F1 1.340(3) . ?
C19 C20 1.377(4) . ?
C20 F2 1.348(3) . ?
C20 C21 1.384(4) . ?
C21 O2 1.348(3) . ?
C21 C22 1.390(4) . ?
C22 F4 1.345(3) . ?
C22 C23 1.356(4) . ?
C23 F3 1.346(3) . ?
C24 O2 1.420(4) . ?
C24 H12 0.9800 . ?
C24 H13 0.9800 . ?
C24 H14 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
O1 C1 H1 109.5 . . ?
O1 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
O1 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
H2 C1 H3 109.5 . . ?
O1 C2 C3 114.8(3) . . ?
O1 C2 C7 125.0(3) . . ?
C3 C2 C7 120.1(3) . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H4 119.8 . . ?
C2 C3 H4 119.8 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H5 119.6 . . ?
C5 C4 H5 119.6 . . ?
C6 C5 C4 117.9(3) . . ?
C6 C5 C8 122.0(3) . . ?
C4 C5 C8 120.0(3) . . ?
C7 C6 C5 121.7(3) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C2 119.1(3) . . ?
C6 C7 H7 120.5 . . ?
C2 C7 H7 120.5 . . ?
C9 C8 C5 175.9(4) . . ?
C8 C9 C10 176.4(4) . . ?
C15 C10 C11 118.6(3) . . ?
C15 C10 C9 121.6(3) . . ?
C11 C10 C9 119.7(3) . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H8 119.6 . . ?
C10 C11 H8 119.6 . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H9 119.9 . . ?
C13 C12 H9 119.9 . . ?
C12 C13 C14 119.2(3) . . ?
C12 C13 C16 120.4(3) . . ?
C14 C13 C16 120.4(3) . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H10 119.7 . . ?
C13 C14 H10 119.7 . . ?
C14 C15 C10 120.6(3) . . ?
C14 C15 H11 119.7 . . ?
C10 C15 H11 119.7 . . ?
C17 C16 C13 177.4(3) . . ?
C16 C17 C18 174.0(3) . . ?
C19 C18 C23 115.2(2) . . ?
C19 C18 C17 123.1(3) . . ?
C23 C18 C17 121.6(3) . . ?
F1 C19 C20 117.7(3) . . ?
F1 C19 C18 119.5(2) . . ?
C20 C19 C18 122.8(3) . . ?
F2 C20 C19 117.4(3) . . ?
F2 C20 C21 121.5(3) . . ?
C19 C20 C21 121.2(3) . . ?
O2 C21 C20 127.5(3) . . ?
O2 C21 C22 116.4(3) . . ?
C20 C21 C22 116.1(2) . . ?
F4 C22 C23 119.1(3) . . ?
F4 C22 C21 118.6(3) . . ?
C23 C22 C21 122.2(3) . . ?
F3 C23 C22 118.4(3) . . ?
F3 C23 C18 119.0(3) . . ?
C22 C23 C18 122.5(3) . . ?
O2 C24 H12 109.5 . . ?
O2 C24 H13 109.5 . . ?
H12 C24 H13 109.5 . . ?
O2 C24 H14 109.5 . . ?
H12 C24 H14 109.5 . . ?
H13 C24 H14 109.5 . . ?
C2 O1 C1 118.1(3) . . ?
C21 O2 C24 121.2(3) . . ?

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
O1 C2 C3 C4 179.1(3) . . . . ?
C7 C2 C3 C4 -0.7(5) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
C3 C4 C5 C8 -174.4(3) . . . . ?
C4 C5 C6 C7 -1.5(4) . . . . ?
C8 C5 C6 C7 174.1(3) . . . . ?
C5 C6 C7 C2 0.7(4) . . . . ?
O1 C2 C7 C6 -179.3(3) . . . . ?
C3 C2 C7 C6 0.5(4) . . . . ?
C15 C10 C11 C12 -0.1(4) . . . . ?
C9 C10 C11 C12 179.8(3) . . . . ?
C10 C11 C12 C13 0.5(5) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C11 C12 C13 C16 178.5(3) . . . . ?
C12 C13 C14 C15 0.8(4) . . . . ?
C16 C13 C14 C15 -178.5(3) . . . . ?
C13 C14 C15 C10 -0.4(5) . . . . ?
C11 C10 C15 C14 0.1(4) . . . . ?
C9 C10 C15 C14 -179.9(3) . . . . ?
C23 C18 C19 F1 -178.6(2) . . . . ?
C17 C18 C19 F1 5.8(4) . . . . ?
C23 C18 C19 C20 2.4(4) . . . . ?
C17 C18 C19 C20 -173.2(3) . . . . ?
F1 C19 C20 F2 0.7(4) . . . . ?
C18 C19 C20 F2 179.8(3) . . . . ?
F1 C19 C20 C21 -179.5(3) . . . . ?
C18 C19 C20 C21 -0.5(4) . . . . ?
F2 C20 C21 O2 -0.2(5) . . . . ?
C19 C20 C21 O2 180.0(3) . . . . ?
F2 C20 C21 C22 178.6(3) . . . . ?
C19 C20 C21 C22 -1.2(4) . . . . ?
O2 C21 C22 F4 -0.2(4) . . . . ?
C20 C21 C22 F4 -179.2(3) . . . . ?
O2 C21 C22 C23 179.7(3) . . . . ?
C20 C21 C22 C23 0.8(4) . . . . ?
F4 C22 C23 F3 -0.6(4) . . . . ?
C21 C22 C23 F3 179.5(3) . . . . ?
F4 C22 C23 C18 -178.7(3) . . . . ?
C21 C22 C23 C18 1.3(5) . . . . ?
C19 C18 C23 F3 179.0(2) . . . . ?
C17 C18 C23 F3 -5.3(4) . . . . ?
C19 C18 C23 C22 -2.8(4) . . . . ?
C17 C18 C23 C22 172.9(3) . . . . ?
C3 C2 O1 C1 -170.0(3) . . . . ?
C7 C2 O1 C1 9.8(5) . . . . ?
C20 C21 O2 C24 -16.7(5) . . . . ?
C22 C21 O2 C24 164.5(3) . . . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.053


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2 and MeOH'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_y_1
_database_code_depnum_ccdc_archive 'CCDC 1838806'
_audit_update_record             
;
2018-04-23 deposited with the CCDC.
2018-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
2,3,4,5,6-Pentafluoro-4-[4-[(4-hexyloxyphenyl)ethynyl]phenylethynyl]benzene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H21 F5 O'
_chemical_formula_sum            'C28 H21 F5 O'
_chemical_formula_weight         468.45

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   11.4515(6)
_cell_length_b                   4.9051(3)
_cell_length_c                   39.555(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2221.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9631
_cell_measurement_theta_min      3.541
_cell_measurement_theta_max      31.366

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79211
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.873
_oxdiff_exptl_absorpt_empirical_full_max 1.315
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17767
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         3.090
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4070
_reflns_number_gt                3772
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.967
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.990

_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       CrystalClear
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
;
Yadokari-XG 2014 (Wakita, Nemoto, et al., 2016)
;
_computing_publication_material  
;
Yadokari-XG 2014 (Wakita, Nemoto, et al., 2016)
;
_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)+(0.0389P)²+0.6274P] 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_abs_structure_details 
;
 Flack x determined using 1623 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4070
_refine_ls_number_parameters     308
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.047
_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 -0.0266(3) -0.2723(6) 0.34972(8) 0.0226(7) Uani 1 1 d . . . . .
C2 C -0.1229(3) -0.4426(6) 0.35212(8) 0.0244(7) Uani 1 1 d . . . . .
C3 C -0.1460(3) -0.6440(6) 0.32918(8) 0.0262(7) Uani 1 1 d . . . . .
C4 C -0.0723(3) -0.6788(7) 0.30185(8) 0.0295(8) Uani 1 1 d . . . . .
C5 C 0.0238(3) -0.5122(7) 0.29819(8) 0.0306(8) Uani 1 1 d . . . . .
C6 C 0.0449(3) -0.3133(7) 0.32160(9) 0.0285(7) Uani 1 1 d . . . . .
C7 C -0.0024(3) -0.0683(7) 0.37442(8) 0.0262(7) Uani 1 1 d . . . . .
C8 C 0.0196(3) 0.1035(6) 0.39524(8) 0.0254(7) Uani 1 1 d . . . . .
C9 C 0.0512(3) 0.3097(6) 0.41917(8) 0.0227(7) Uani 1 1 d . . . . .
C10 C 0.1639(3) 0.4207(6) 0.41827(8) 0.0261(7) Uani 1 1 d . . . . .
H1 H 0.218388 0.358564 0.401893 0.031 Uiso 1 1 calc R U . . .
C11 C 0.1959(3) 0.6190(7) 0.44098(8) 0.0260(7) Uani 1 1 d . . . . .
H2 H 0.272836 0.691172 0.440157 0.031 Uiso 1 1 calc R U . . .
C12 C 0.1177(3) 0.7171(6) 0.46530(8) 0.0220(6) Uani 1 1 d . . . . .
C13 C 0.0047(3) 0.6084(6) 0.46586(8) 0.0260(7) Uani 1 1 d . . . . .
H3 H -0.050377 0.674359 0.481844 0.031 Uiso 1 1 calc R U . . .
C14 C -0.0275(3) 0.4067(7) 0.44349(8) 0.0261(7) Uani 1 1 d . . . . .
H4 H -0.103984 0.332368 0.444566 0.031 Uiso 1 1 calc R U . . .
C15 C 0.1541(3) 0.9255(6) 0.48840(8) 0.0249(7) Uani 1 1 d . . . . .
C16 C 0.1885(3) 1.0981(6) 0.50745(8) 0.0248(7) Uani 1 1 d . . . . .
C17 C 0.2354(3) 1.2993(6) 0.53011(8) 0.0239(7) Uani 1 1 d . . . . .
C18 C 0.3545(3) 1.3640(7) 0.52878(8) 0.0282(7) Uani 1 1 d . . . . .
H5 H 0.402860 1.277352 0.512489 0.034 Uiso 1 1 calc R U . . .
C19 C 0.4025(3) 1.5509(7) 0.55066(9) 0.0287(7) Uani 1 1 d . . . . .
H6 H 0.483571 1.591047 0.549494 0.034 Uiso 1 1 calc R U . . .
C20 C 0.3331(3) 1.6808(6) 0.57442(8) 0.0262(7) Uani 1 1 d . . . . .
C21 C 0.2146(3) 1.6267(7) 0.57577(9) 0.0289(8) Uani 1 1 d . . . . .
H7 H 0.166190 1.719404 0.591524 0.035 Uiso 1 1 calc R U . . .
C22 C 0.1671(3) 1.4353(7) 0.55382(8) 0.0278(7) Uani 1 1 d . . . . .
H8 H 0.085988 1.396197 0.555032 0.033 Uiso 1 1 calc R U . . .
O1 O 0.3918(2) 1.8561(5) 0.59528(6) 0.0359(6) Uani 1 1 d . . . . .
C23 C 0.3264(3) 2.0033(8) 0.62023(9) 0.0391(9) Uani 1 1 d . . . . .
H9 H 0.282940 1.875250 0.634918 0.047 Uiso 1 1 calc R U . . .
H10 H 0.269757 2.126995 0.609179 0.047 Uiso 1 1 calc R U . . .
C24 C 0.4131(4) 2.1650(7) 0.64082(10) 0.0426(10) Uani 1 1 d . . . . .
H11 H 0.369967 2.291335 0.655826 0.051 Uiso 1 1 calc R U . . .
H12 H 0.461537 2.276239 0.625354 0.051 Uiso 1 1 calc R U . . .
C25 C 0.4926(4) 1.9874(8) 0.66219(10) 0.0413(9) Uani 1 1 d . . . . .
H13 H 0.537680 1.866175 0.647039 0.050 Uiso 1 1 calc R U . . .
H14 H 0.443690 1.870544 0.676895 0.050 Uiso 1 1 calc R U . . .
C26 C 0.5773(4) 2.1455(8) 0.68419(10) 0.0442(10) Uani 1 1 d . . . . .
H15 H 0.624059 2.268032 0.669631 0.053 Uiso 1 1 calc R U . . .
H16 H 0.532249 2.260787 0.700066 0.053 Uiso 1 1 calc R U . . .
C27 C 0.6593(4) 1.9660(9) 0.70428(11) 0.0535(11) Uani 1 1 d . . . . .
H17 H 0.708167 1.860381 0.688316 0.064 Uiso 1 1 calc R U . . .
H18 H 0.612418 1.834370 0.717523 0.064 Uiso 1 1 calc R U . . .
C28 C 0.7391(4) 2.1203(11) 0.72830(12) 0.0622(14) Uani 1 1 d . . . . .
H19 H 0.783236 2.257657 0.715647 0.093 Uiso 1 1 calc R U . . .
H20 H 0.793377 1.992425 0.739024 0.093 Uiso 1 1 calc R U . . .
H21 H 0.691961 2.210310 0.745716 0.093 Uiso 1 1 calc R U . . .
F1 F -0.19541(18) -0.4139(4) 0.37854(5) 0.0398(5) Uani 1 1 d . . . . .
F2 F -0.23603(18) -0.8137(4) 0.33332(6) 0.0416(6) Uani 1 1 d . . . . .
F3 F -0.0926(2) -0.8782(4) 0.27945(5) 0.0479(6) Uani 1 1 d . . . . .
F4 F 0.0946(2) -0.5448(5) 0.27151(6) 0.0558(7) Uani 1 1 d . . . . .
F5 F 0.13803(19) -0.1515(5) 0.31698(6) 0.0454(6) 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(4) . ?
C1 C6 1.396(5) . ?
C1 C7 1.426(5) . ?
C2 F1 1.342(4) . ?
C2 C3 1.367(4) . ?
C3 F2 1.336(4) . ?
C3 C4 1.382(5) . ?
C4 F3 1.340(4) . ?
C4 C5 1.379(5) . ?
C5 F4 1.341(4) . ?
C5 C6 1.366(5) . ?
C6 F5 1.342(4) . ?
C7 C8 1.205(4) . ?
C8 C9 1.432(4) . ?
C9 C10 1.401(5) . ?
C9 C14 1.401(5) . ?
C10 C11 1.374(5) . ?
C10 H1 0.9500 . ?
C11 C12 1.399(5) . ?
C11 H2 0.9500 . ?
C12 C13 1.400(4) . ?
C12 C15 1.433(4) . ?
C13 C14 1.377(4) . ?
C13 H3 0.9500 . ?
C14 H4 0.9500 . ?
C15 C16 1.200(4) . ?
C16 C17 1.437(5) . ?
C17 C22 1.391(5) . ?
C17 C18 1.401(5) . ?
C18 C19 1.376(5) . ?
C18 H5 0.9500 . ?
C19 C20 1.386(5) . ?
C19 H6 0.9500 . ?
C20 O1 1.369(4) . ?
C20 C21 1.384(5) . ?
C21 C22 1.389(5) . ?
C21 H7 0.9500 . ?
C22 H8 0.9500 . ?
O1 C23 1.434(4) . ?
C23 C24 1.509(5) . ?
C23 H9 0.9900 . ?
C23 H10 0.9900 . ?
C24 C25 1.517(5) . ?
C24 H11 0.9900 . ?
C24 H12 0.9900 . ?
C25 C26 1.516(5) . ?
C25 H13 0.9900 . ?
C25 H14 0.9900 . ?
C26 C27 1.513(6) . ?
C26 H15 0.9900 . ?
C26 H16 0.9900 . ?
C27 C28 1.519(6) . ?
C27 H17 0.9900 . ?
C27 H18 0.9900 . ?
C28 H19 0.9800 . ?
C28 H20 0.9800 . ?
C28 H21 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 C1 C6 115.7(3) . . ?
C2 C1 C7 122.1(3) . . ?
C6 C1 C7 122.2(3) . . ?
F1 C2 C3 118.3(3) . . ?
F1 C2 C1 118.8(3) . . ?
C3 C2 C1 122.9(3) . . ?
F2 C3 C2 121.2(3) . . ?
F2 C3 C4 119.4(3) . . ?
C2 C3 C4 119.4(3) . . ?
F3 C4 C5 120.1(3) . . ?
F3 C4 C3 120.1(3) . . ?
C5 C4 C3 119.7(3) . . ?
F4 C5 C6 120.8(3) . . ?
F4 C5 C4 119.6(3) . . ?
C6 C5 C4 119.6(3) . . ?
F5 C6 C5 118.1(3) . . ?
F5 C6 C1 119.3(3) . . ?
C5 C6 C1 122.6(3) . . ?
C8 C7 C1 179.2(4) . . ?
C7 C8 C9 177.1(4) . . ?
C10 C9 C14 118.5(3) . . ?
C10 C9 C8 119.4(3) . . ?
C14 C9 C8 122.1(3) . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H1 119.9 . . ?
C9 C10 H1 119.9 . . ?
C10 C11 C12 121.5(3) . . ?
C10 C11 H2 119.3 . . ?
C12 C11 H2 119.3 . . ?
C13 C12 C11 118.1(3) . . ?
C13 C12 C15 122.0(3) . . ?
C11 C12 C15 119.8(3) . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H3 119.6 . . ?
C12 C13 H3 119.6 . . ?
C13 C14 C9 120.8(3) . . ?
C13 C14 H4 119.6 . . ?
C9 C14 H4 119.6 . . ?
C16 C15 C12 177.7(4) . . ?
C15 C16 C17 177.2(4) . . ?
C22 C17 C18 117.6(3) . . ?
C22 C17 C16 122.6(3) . . ?
C18 C17 C16 119.7(3) . . ?
C19 C18 C17 121.1(3) . . ?
C19 C18 H5 119.5 . . ?
C17 C18 H5 119.5 . . ?
C18 C19 C20 120.2(3) . . ?
C18 C19 H6 119.9 . . ?
C20 C19 H6 119.9 . . ?
O1 C20 C21 125.4(3) . . ?
O1 C20 C19 114.6(3) . . ?
C21 C20 C19 120.0(3) . . ?
C20 C21 C22 119.3(3) . . ?
C20 C21 H7 120.4 . . ?
C22 C21 H7 120.4 . . ?
C21 C22 C17 121.7(3) . . ?
C21 C22 H8 119.2 . . ?
C17 C22 H8 119.2 . . ?
C20 O1 C23 118.3(3) . . ?
O1 C23 C24 107.0(3) . . ?
O1 C23 H9 110.3 . . ?
C24 C23 H9 110.3 . . ?
O1 C23 H10 110.3 . . ?
C24 C23 H10 110.3 . . ?
H9 C23 H10 108.6 . . ?
C23 C24 C25 113.2(3) . . ?
C23 C24 H11 108.9 . . ?
C25 C24 H11 108.9 . . ?
C23 C24 H12 108.9 . . ?
C25 C24 H12 108.9 . . ?
H11 C24 H12 107.8 . . ?
C24 C25 C26 114.2(3) . . ?
C24 C25 H13 108.7 . . ?
C26 C25 H13 108.7 . . ?
C24 C25 H14 108.7 . . ?
C26 C25 H14 108.7 . . ?
H13 C25 H14 107.6 . . ?
C27 C26 C25 113.7(3) . . ?
C27 C26 H15 108.8 . . ?
C25 C26 H15 108.8 . . ?
C27 C26 H16 108.8 . . ?
C25 C26 H16 108.8 . . ?
H15 C26 H16 107.7 . . ?
C26 C27 C28 114.3(4) . . ?
C26 C27 H17 108.7 . . ?
C28 C27 H17 108.7 . . ?
C26 C27 H18 108.7 . . ?
C28 C27 H18 108.7 . . ?
H17 C27 H18 107.6 . . ?
C27 C28 H19 109.5 . . ?
C27 C28 H20 109.5 . . ?
H19 C28 H20 109.5 . . ?
C27 C28 H21 109.5 . . ?
H19 C28 H21 109.5 . . ?
H20 C28 H21 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
C6 C1 C2 F1 -179.9(3) . . . . ?
C7 C1 C2 F1 0.0(5) . . . . ?
C6 C1 C2 C3 1.8(5) . . . . ?
C7 C1 C2 C3 -178.2(3) . . . . ?
F1 C2 C3 F2 -2.0(5) . . . . ?
C1 C2 C3 F2 176.3(3) . . . . ?
F1 C2 C3 C4 -179.6(3) . . . . ?
C1 C2 C3 C4 -1.4(5) . . . . ?
F2 C3 C4 F3 1.2(5) . . . . ?
C2 C3 C4 F3 178.9(3) . . . . ?
F2 C3 C4 C5 -177.1(3) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
F3 C4 C5 F4 2.2(5) . . . . ?
C3 C4 C5 F4 -179.5(3) . . . . ?
F3 C4 C5 C6 -178.6(3) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
F4 C5 C6 F5 0.3(5) . . . . ?
C4 C5 C6 F5 -178.9(3) . . . . ?
F4 C5 C6 C1 180.0(3) . . . . ?
C4 C5 C6 C1 0.8(5) . . . . ?
C2 C1 C6 F5 178.2(3) . . . . ?
C7 C1 C6 F5 -1.8(5) . . . . ?
C2 C1 C6 C5 -1.5(5) . . . . ?
C7 C1 C6 C5 178.5(3) . . . . ?
C14 C9 C10 C11 0.4(5) . . . . ?
C8 C9 C10 C11 179.9(3) . . . . ?
C9 C10 C11 C12 -0.5(5) . . . . ?
C10 C11 C12 C13 -0.3(5) . . . . ?
C10 C11 C12 C15 -179.5(3) . . . . ?
C11 C12 C13 C14 1.3(5) . . . . ?
C15 C12 C13 C14 -179.5(3) . . . . ?
C12 C13 C14 C9 -1.4(5) . . . . ?
C10 C9 C14 C13 0.6(5) . . . . ?
C8 C9 C14 C13 -179.0(3) . . . . ?
C22 C17 C18 C19 1.4(5) . . . . ?
C16 C17 C18 C19 -178.4(3) . . . . ?
C17 C18 C19 C20 -0.5(5) . . . . ?
C18 C19 C20 O1 178.3(3) . . . . ?
C18 C19 C20 C21 -1.3(5) . . . . ?
O1 C20 C21 C22 -177.5(3) . . . . ?
C19 C20 C21 C22 2.0(5) . . . . ?
C20 C21 C22 C17 -1.0(5) . . . . ?
C18 C17 C22 C21 -0.7(5) . . . . ?
C16 C17 C22 C21 179.2(3) . . . . ?
C21 C20 O1 C23 -1.7(5) . . . . ?
C19 C20 O1 C23 178.8(3) . . . . ?
C20 O1 C23 C24 176.4(3) . . . . ?
O1 C23 C24 C25 -67.7(4) . . . . ?
C23 C24 C25 C26 -177.7(3) . . . . ?
C24 C25 C26 C27 -177.6(4) . . . . ?
C25 C26 C27 C28 -175.9(4) . . . . ?

_refine_diff_density_max         0.153
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.035


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2 and MeOH'
_exptl_crystal_preparation       Luminescent
