# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_fs40
_database_code_depnum_ccdc_archive 'CCDC 2009230'
loop_
_audit_author_name
_audit_author_address
'Jian-Bin Lin'
;Memorial University of Newfoundland
Canada
;
_audit_update_record             
;
2020-06-11 deposited with the CCDC.	2020-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
5-(4,5-bis(methylthio)-1,3-dithiol-2-ylidene)pyren-4(5H)-one
_chemical_formula_moiety         'C21 H14 O S4'
_chemical_formula_sum            'C21 H14 O S4'
_chemical_formula_weight         410.56
_chemical_melting_point          '191.3 - 191.8'
_chemical_oxdiff_formula         C21H14OS4
_chemical_oxdiff_usercomment     orange
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.15876(6)
_cell_length_b                   20.4115(3)
_cell_length_c                   16.5822(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.4856(12)
_cell_angle_gamma                90
_cell_volume                     1734.90(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15183
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.0620
_cell_measurement_theta_min      3.4280
_shelx_estimated_absorpt_T_max   0.846
_shelx_estimated_absorpt_T_min   0.440
_exptl_absorpt_coefficient_mu    5.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -3 -10 0.0298
0 11 -6 0.0277
0 -13 -2 0.0100
0 12 -4 0.0356
0 -12 4 0.0150
-3 -2 0 0.0953
3 0 -3 0.0885
0 3 10 0.0037
0 -9 8 0.0067

_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.034
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.2095 -3.0386 -10.4680 -0.0032 -0.0085 -1.0000
0.1287 11.2311 -5.6995 0.8304 0.4505 -0.3279
0.0032 -13.1021 -1.5723 -0.8191 -0.4443 -0.3629
0.4367 12.4123 -3.6180 0.9178 0.3803 -0.1138
-0.4377 -12.4056 3.6326 -0.9178 -0.3800 0.1152
-3.3023 -1.5022 -0.0944 -0.5643 0.8210 -0.0871
3.2775 0.4888 -3.3511 0.5491 -0.7994 -0.2438
-0.2095 3.0386 10.4680 0.0032 0.0085 1.0000
-0.1620 -9.0197 7.8733 -0.7265 -0.3951 0.5623

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            42353
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.406
_diffrn_reflns_theta_min         3.447
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  28.00   0.50    2.00    --  -47.82  19.00 -90.00   88
  2  ω    -16.00  28.00   0.50    2.00    --  -47.82  19.00 -60.00   88
  3  ω    -16.00  28.00   0.50    2.00    --  -47.82  19.00 -30.00   88
  4  ω    -16.00  28.00   0.50    2.00    --  -47.82  19.00 120.00   88
  5  ω    -43.00 -14.00   0.50    8.00    --  -86.25  45.00  90.00   58
  6  ω    -43.00 -14.00   0.50    8.00    --  -86.25  45.00  60.00   58
  7  ω    -82.00   0.00   0.50    2.00    --  -47.82 108.00-102.00  164
  8  ω    -43.00 -14.00   0.50    8.00    --  -86.25  45.00-120.00   58
  9  ω    -59.00  25.00   0.50    2.00    --  -47.82  57.00-180.00  168
 10  ω    -65.00 -13.00   0.50    8.00    --  -86.25  61.00 -90.00  104
 11  ω    -82.00 -13.00   0.50    8.00    --  -86.25 108.00-102.00  138
 12  ω   -119.00 -33.00   0.50    2.00    --  -47.82 -57.00-120.00  172
 13  ω   -119.00 -73.00   0.50    2.00    --  -47.82-125.00   0.00   92
 14  ω   -119.00 -73.00   0.50    2.00    --  -47.82-125.00 -30.00   92
 15  ω   -119.00 -73.00   0.50    2.00    --  -47.82-125.00-120.00   92
 16  ω   -119.00 -73.00   0.50    2.00    --  -47.82-125.00-150.00   92
 17  ω   -119.00 -25.00   0.50    2.00    --  -47.82 -77.00-150.00  188
 18  ω   -119.00 -25.00   0.50    2.00    --  -47.82 -77.00 -30.00  188
 19  ω     21.00  86.00   0.50    2.00    --   47.82-108.00 160.00  130
 20  ω     35.00 107.00   0.50    8.00    --  107.75-108.00 160.00  144
 21  ω     35.00  79.00   0.50    8.00    --  107.75 -61.00   0.00   88
 22  ω     35.00  79.00   0.50    8.00    --  107.75 -61.00  60.00   88
 23  ω     35.00  79.00   0.50    8.00    --  107.75 -61.00 120.00   88
 24  ω     35.00 106.00   0.50    8.00    --  107.75 -97.00  58.18  142
 25  ω     35.00 112.00   0.50    8.00    --  107.75-125.00 120.00  154
 26  ω     35.00 112.00   0.50    8.00    --  107.75-125.00  60.00  154
 27  ω     35.00  79.00   0.50    8.00    --  107.75 -61.00 -60.00   88
 28  ω     35.00 106.00   0.50    8.00    --  107.75 -94.00 -60.00  142
 29  ω     35.00 106.00   0.50    8.00    --  107.75 -94.00-180.00  142
 30  ω     35.00 112.00   0.50    8.00    --  107.75-125.00-120.00  154
 31  ω     35.00  79.00   0.50    8.00    --  107.75 -61.00-150.00   88
 32  ω     35.00  79.00   0.50    8.00    --  107.75 -61.00-180.00   88
 33  ω     35.00 106.00   0.50    8.00    --  107.75 -94.00-150.00  142
 34  ω     35.00  79.00   0.50    8.00    --  107.75 -61.00 -30.00   88
 35  ω     35.00 106.00   0.50    8.00    --  107.75 -94.00 -90.00  142
 36  ω     35.00 112.00   0.50    8.00    --  107.75-125.00-150.00  154
 37  ω     35.00 106.00   0.50    8.00    --  107.75 -94.00 -30.00  142
 38  ω     35.00 106.00   0.50    8.00    --  107.75 -94.00  90.00  142
 39  ω     35.00 112.00   0.50    8.00    --  107.75-125.00  90.00  154
 40  ω     35.00  79.00   0.50    8.00    --  107.75 -61.00  30.00   88
 41  ω     95.00 178.00   0.50    8.00    --  107.75  30.00 150.00  166
 42  ω     95.00 178.00   0.50    8.00    --  107.75  45.00  30.00  166
 43  ω    104.00 178.00   0.50    8.00    --  107.75 108.00-102.00  148
 44  ω     95.00 178.00   0.50    8.00    --  107.75  45.00 -90.00  166
 45  ω     95.00 178.00   0.50    8.00    --  107.75 125.00   0.00  166
 46  ω     95.00 178.00   0.50    8.00    --  107.75  45.00 -30.00  166
 47  ω     95.00 178.00   0.50    8.00    --  107.75  30.00 120.00  166
 48  ω     95.00 178.00   0.50    8.00    --  107.75  30.00   0.00  166
 49  ω     91.00 178.00   0.50    8.00    --  107.75  61.00-120.00  174
 50  ω     35.00 112.00   0.50    8.00    --  107.75-125.00 -90.00  154
 51  ω   -119.00 -25.00   0.50    2.00    --  -47.82 -77.00  60.00  188
 52  ω   -119.00 -25.00   0.50    2.00    --  -47.82 -77.00 150.00  188
 53  ω   -119.00 -25.00   0.50    2.00    --  -47.82 -77.00   0.00  188
 54  ω   -159.00 -82.00   0.50    8.00    --  -86.25-108.00 160.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1420205000
_diffrn_orient_matrix_UB_12      0.0644182000
_diffrn_orient_matrix_UB_13      -0.0155478000
_diffrn_orient_matrix_UB_21      -0.2643811000
_diffrn_orient_matrix_UB_22      0.0356206000
_diffrn_orient_matrix_UB_23      -0.0148148000
_diffrn_orient_matrix_UB_31      0.0161429000
_diffrn_orient_matrix_UB_32      0.0167837000
_diffrn_orient_matrix_UB_33      0.0909760000
_diffrn_oxdiff_digest_frames     
;
018b4c80292012d42759a4cd63a1afbe91071145c4c
;
_diffrn_oxdiff_digest_hkl        
;
0190191d136d371615d818c40f9c35fe9f7ede
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3351
_reflns_number_total             3667
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3667
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0654P)²+1.3152P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1067
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
S1 S 0.08928(9) 0.66912(2) 0.53076(3) 0.02109(13) Uani 1 1 d . . . . .
S2 S 0.30228(9) 0.64034(3) 0.69642(3) 0.02271(14) Uani 1 1 d . . . . .
S3 S -0.06668(10) 0.52727(3) 0.71445(3) 0.02620(14) Uani 1 1 d . . . . .
S4 S -0.31146(10) 0.55992(3) 0.52969(3) 0.02751(15) Uani 1 1 d . . . . .
O1 O 0.3166(3) 0.75440(8) 0.47165(9) 0.0284(3) Uani 1 1 d . . . . .
C1 C 0.0543(4) 0.58856(10) 0.65499(12) 0.0223(4) Uani 1 1 d . . . . .
C2 C -0.0466(4) 0.60287(10) 0.57864(12) 0.0214(4) Uani 1 1 d . . . . .
C3 C 0.3204(4) 0.68943(10) 0.61237(12) 0.0206(4) Uani 1 1 d . . . . .
C4 C 0.5015(4) 0.74000(10) 0.60674(12) 0.0201(4) Uani 1 1 d . . . . .
C5 C 0.4856(4) 0.77159(10) 0.52795(12) 0.0230(4) Uani 1 1 d . . . . .
C6 C 0.6712(4) 0.82331(10) 0.51296(12) 0.0225(4) Uani 1 1 d . . . . .
C7 C 0.6500(4) 0.85435(11) 0.43773(13) 0.0256(4) Uani 1 1 d . . . . .
H7 H 0.511267 0.843132 0.397477 0.031 Uiso 1 1 calc R . . . .
C8 C 0.8303(5) 0.90160(11) 0.42113(14) 0.0295(5) Uani 1 1 d . . . . .
H8 H 0.816509 0.922177 0.369439 0.035 Uiso 1 1 calc R . . . .
C9 C 1.0301(4) 0.91856(11) 0.48026(14) 0.0282(4) Uani 1 1 d . . . . .
H9 H 1.154407 0.950419 0.468276 0.034 Uiso 1 1 calc R . . . .
C10 C 1.0528(4) 0.88988(11) 0.55708(13) 0.0249(4) Uani 1 1 d . . . . .
C11 C 0.8691(4) 0.84070(10) 0.57442(12) 0.0217(4) Uani 1 1 d . . . . .
C12 C 0.8852(4) 0.81117(10) 0.65300(12) 0.0209(4) Uani 1 1 d . . . . .
C13 C 0.7004(4) 0.76225(10) 0.67168(12) 0.0213(4) Uani 1 1 d . . . . .
C14 C 0.7190(4) 0.74003(11) 0.75140(13) 0.0271(4) Uani 1 1 d . . . . .
H14 H 0.593983 0.709318 0.765999 0.033 Uiso 1 1 calc R . . . .
C15 C 0.9154(4) 0.76128(11) 0.81105(13) 0.0276(5) Uani 1 1 d . . . . .
H15 H 0.921374 0.744860 0.864840 0.033 Uiso 1 1 calc R . . . .
C16 C 1.0982(4) 0.80544(11) 0.79224(13) 0.0260(4) Uani 1 1 d . . . . .
H16 H 1.234855 0.818258 0.832367 0.031 Uiso 1 1 calc R . . . .
C17 C 1.0846(4) 0.83185(10) 0.71400(13) 0.0230(4) Uani 1 1 d . . . . .
C18 C 1.2705(4) 0.87959(11) 0.69386(13) 0.0260(4) Uani 1 1 d . . . . .
H18 H 1.407920 0.892027 0.733943 0.031 Uiso 1 1 calc R . . . .
C19 C 1.2562(4) 0.90758(10) 0.61919(13) 0.0253(4) Uani 1 1 d . . . . .
H19 H 1.382401 0.939232 0.608085 0.030 Uiso 1 1 calc R . . . .
C20 C 0.2245(4) 0.50290(12) 0.77804(14) 0.0299(5) Uani 1 1 d . . . . .
H20A H 0.367455 0.496866 0.744526 0.045 Uiso 1 1 calc GR . . . .
H20B H 0.192121 0.461652 0.805430 0.045 Uiso 1 1 calc GR . . . .
H20C H 0.272023 0.536968 0.818678 0.045 Uiso 1 1 calc GR . . . .
C21 C -0.3233(5) 0.58690(15) 0.42668(15) 0.0427(6) Uani 1 1 d . . . . .
H21A H -0.465336 0.564315 0.393534 0.064 Uiso 1 1 calc GR . . . .
H21B H -0.157208 0.576892 0.405970 0.064 Uiso 1 1 calc GR . . . .
H21C H -0.353900 0.634281 0.424100 0.064 Uiso 1 1 calc GR . . . .


_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
S1 C2 1.754(2) . ?
S1 C3 1.750(2) . ?
S2 C1 1.740(2) . ?
S2 C3 1.728(2) . ?
S3 C1 1.751(2) . ?
S3 C20 1.805(2) . ?
S4 C2 1.745(2) . ?
S4 C21 1.789(2) . ?
O1 C5 1.254(3) . ?
C1 C2 1.346(3) . ?
C3 C4 1.402(3) . ?
C4 C5 1.451(3) . ?
C4 C13 1.473(3) . ?
C5 C6 1.465(3) . ?
C6 C7 1.392(3) . ?
C6 C11 1.404(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.389(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.395(3) . ?
C10 C11 1.432(3) . ?
C10 C19 1.431(3) . ?
C11 C12 1.430(3) . ?
C12 C13 1.438(3) . ?
C12 C17 1.423(3) . ?
C13 C14 1.391(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.403(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.366(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.399(3) . ?
C17 C18 1.433(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.358(3) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C3 S1 C2 96.02(10) . . ?
C3 S2 C1 97.95(10) . . ?
C1 S3 C20 101.52(10) . . ?
C2 S4 C21 103.30(11) . . ?
S2 C1 S3 120.31(12) . . ?
C2 C1 S2 115.40(16) . . ?
C2 C1 S3 124.06(16) . . ?
S4 C2 S1 120.59(12) . . ?
C1 C2 S1 117.47(16) . . ?
C1 C2 S4 121.89(16) . . ?
S2 C3 S1 113.09(11) . . ?
C4 C3 S1 121.59(15) . . ?
C4 C3 S2 125.30(15) . . ?
C3 C4 C5 114.63(17) . . ?
C3 C4 C13 126.34(18) . . ?
C5 C4 C13 119.02(18) . . ?
O1 C5 C4 120.66(19) . . ?
O1 C5 C6 119.22(19) . . ?
C4 C5 C6 120.10(18) . . ?
C7 C6 C5 119.56(19) . . ?
C7 C6 C11 120.82(19) . . ?
C11 C6 C5 119.62(19) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.5(2) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.4(2) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C11 119.24(19) . . ?
C9 C10 C19 122.0(2) . . ?
C19 C10 C11 118.72(19) . . ?
C6 C11 C10 118.35(19) . . ?
C6 C11 C12 121.18(19) . . ?
C12 C11 C10 120.46(18) . . ?
C11 C12 C13 121.15(18) . . ?
C17 C12 C11 119.06(19) . . ?
C17 C12 C13 119.78(19) . . ?
C12 C13 C4 118.73(18) . . ?
C14 C13 C4 124.20(19) . . ?
C14 C13 C12 117.05(18) . . ?
C13 C14 H14 118.8 . . ?
C13 C14 C15 122.4(2) . . ?
C15 C14 H14 118.8 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.17(19) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C18 119.03(19) . . ?
C16 C17 C12 120.08(19) . . ?
C16 C17 C18 120.89(19) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 C17 121.99(19) . . ?
C19 C18 H18 119.0 . . ?
C10 C19 H19 119.7 . . ?
C18 C19 C10 120.66(19) . . ?
C18 C19 H19 119.7 . . ?
S3 C20 H20A 109.5 . . ?
S3 C20 H20B 109.5 . . ?
S3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
S4 C21 H21A 109.5 . . ?
S4 C21 H21B 109.5 . . ?
S4 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
S1 C3 C4 C5 -2.0(3) . . . . ?
S1 C3 C4 C13 178.62(16) . . . . ?
S2 C1 C2 S1 1.8(2) . . . . ?
S2 C1 C2 S4 -175.53(11) . . . . ?
S2 C3 C4 C5 176.66(15) . . . . ?
S2 C3 C4 C13 -2.7(3) . . . . ?
S3 C1 C2 S1 176.39(11) . . . . ?
S3 C1 C2 S4 -1.0(3) . . . . ?
O1 C5 C6 C7 2.7(3) . . . . ?
O1 C5 C6 C11 -176.94(19) . . . . ?
C1 S2 C3 S1 2.51(13) . . . . ?
C1 S2 C3 C4 -176.28(18) . . . . ?
C2 S1 C3 S2 -1.70(13) . . . . ?
C2 S1 C3 C4 177.13(17) . . . . ?
C3 S1 C2 S4 177.33(13) . . . . ?
C3 S1 C2 C1 -0.07(19) . . . . ?
C3 S2 C1 S3 -177.41(13) . . . . ?
C3 S2 C1 C2 -2.64(19) . . . . ?
C3 C4 C5 O1 1.5(3) . . . . ?
C3 C4 C5 C6 -177.38(18) . . . . ?
C3 C4 C13 C12 174.65(19) . . . . ?
C3 C4 C13 C14 -6.8(3) . . . . ?
C4 C5 C6 C7 -178.44(19) . . . . ?
C4 C5 C6 C11 1.9(3) . . . . ?
C4 C13 C14 C15 178.4(2) . . . . ?
C5 C4 C13 C12 -4.7(3) . . . . ?
C5 C4 C13 C14 173.8(2) . . . . ?
C5 C6 C7 C8 -177.3(2) . . . . ?
C5 C6 C11 C10 177.95(18) . . . . ?
C5 C6 C11 C12 -3.2(3) . . . . ?
C6 C7 C8 C9 -0.9(3) . . . . ?
C6 C11 C12 C13 0.5(3) . . . . ?
C6 C11 C12 C17 -178.12(19) . . . . ?
C7 C6 C11 C10 -1.7(3) . . . . ?
C7 C6 C11 C12 177.16(19) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
C8 C9 C10 C11 1.5(3) . . . . ?
C8 C9 C10 C19 -179.1(2) . . . . ?
C9 C10 C11 C6 -0.2(3) . . . . ?
C9 C10 C11 C12 -179.05(19) . . . . ?
C9 C10 C19 C18 178.9(2) . . . . ?
C10 C11 C12 C13 179.27(18) . . . . ?
C10 C11 C12 C17 0.7(3) . . . . ?
C11 C6 C7 C8 2.3(3) . . . . ?
C11 C10 C19 C18 -1.8(3) . . . . ?
C11 C12 C13 C4 3.5(3) . . . . ?
C11 C12 C13 C14 -175.10(19) . . . . ?
C11 C12 C17 C16 177.58(19) . . . . ?
C11 C12 C17 C18 -2.7(3) . . . . ?
C12 C13 C14 C15 -3.1(3) . . . . ?
C12 C17 C18 C19 2.6(3) . . . . ?
C13 C4 C5 O1 -179.11(18) . . . . ?
C13 C4 C5 C6 2.0(3) . . . . ?
C13 C12 C17 C16 -1.0(3) . . . . ?
C13 C12 C17 C18 178.66(19) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C17 2.6(3) . . . . ?
C15 C16 C17 C12 -2.1(3) . . . . ?
C15 C16 C17 C18 178.3(2) . . . . ?
C16 C17 C18 C19 -177.7(2) . . . . ?
C17 C12 C13 C4 -177.89(18) . . . . ?
C17 C12 C13 C14 3.5(3) . . . . ?
C17 C18 C19 C10 -0.3(3) . . . . ?
C19 C10 C11 C6 -179.58(19) . . . . ?
C19 C10 C11 C12 1.6(3) . . . . ?
C20 S3 C1 S2 -35.30(16) . . . . ?
C20 S3 C1 C2 150.4(2) . . . . ?
C21 S4 C2 S1 13.60(17) . . . . ?
C21 S4 C2 C1 -169.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.455
_oxdiff_exptl_absorpt_empirical_full_min 0.602
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/DCM'
_chemical_compound_source        Pyrene
_chemical_properties_physical    Efflorescent,Oxygen-sensitive
####################################################################### 
# 
# 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_fs67
_database_code_depnum_ccdc_archive 'CCDC 2009231'
loop_
_audit_author_name
_audit_author_address
'Jian-Bin Lin'
;Memorial University of Newfoundland
Canada
;
_audit_update_record             
;
2020-06-11 deposited with the CCDC.	2020-09-25 downloaded from the CCDC.
;
_audit_creation_date             2020-01-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        5-(dibromomethylene)pyren-4(5H)-one
_chemical_formula_moiety         'C17 H8 Br2 O'
_chemical_formula_sum            'C17 H8 Br2 O'
_chemical_formula_weight         388.05
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H8Br2O
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'
Br Br -0.6763 1.2805 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   3.88283(4)
_cell_length_b                   18.75250(17)
_cell_length_c                   17.4959(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.4372(10)
_cell_angle_gamma                90
_cell_volume                     1272.77(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8163
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.9260
_cell_measurement_theta_min      3.4500
_shelx_estimated_absorpt_T_max   0.691
_shelx_estimated_absorpt_T_min   0.447
_exptl_absorpt_coefficient_mu    7.994
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.025
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16339
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.239
_diffrn_reflns_theta_min         3.457
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  39.00   0.50    0.06    --   47.95 -29.00 -82.00  130
  2  ω     35.00  79.00   0.50    0.25    --  107.75 -61.00 -90.00   88
  3  ω     35.00 131.00   0.50    0.25    --  107.75 -77.00 -90.00  192
  4  ω     94.00 178.00   0.50    0.25    --  107.75  15.00  30.00  168
  5  ω     95.00 178.00   0.50    0.25    --  107.75  29.00  78.00  166
  6  ω     95.00 178.00   0.50    0.25    --  107.75  30.00 120.00  166
  7  ω     36.00 122.00   0.50    0.06    --   47.95  29.00  78.00  172
  8  ω     35.00 106.00   0.50    0.25    --  107.75 -94.00  30.00  142
  9  ω     35.00 112.00   0.50    0.25    --  107.75-125.00 -90.00  154
 10  ω     35.00 106.00   0.50    0.25    --  107.75 -94.00-180.00  142
 11  ω     35.00  79.00   0.50    0.25    --  107.75 -61.00-150.00   88
 12  ω     35.00  79.00   0.50    0.25    --  107.75 -61.00 -60.00   88
 13  ω     35.00  79.00   0.50    0.25    --  107.75 -61.00   0.00   88
 14  ω     35.00  79.00   0.50    0.25    --  107.75 -61.00  90.00   88
 15  ω     35.00  79.00   0.50    0.25    --  107.75 -61.00 150.00   88
 16  ω     35.00 106.00   0.50    0.25    --  107.75 -94.00 150.00  142
 17  ω     35.00 106.00   0.50    0.25    --  107.75 -94.00 120.00  142
 18  ω     25.00 120.00   0.50    0.06    --   47.95  77.00-120.00  190
 19  ω     95.00 178.00   0.50    0.25    --  107.75  45.00-150.00  166
 20  ω     25.00 120.00   0.50    0.06    --   47.95  77.00 150.00  190
 21  ω    -25.00  27.00   0.50    0.06    --  -47.95  29.00  78.00  104
 22  ω    -43.00 -14.00   0.50    0.25    --  -86.25  45.00 -90.00   58
 23  ω    -43.00 -14.00   0.50    0.25    --  -86.25  45.00-150.00   58
 24  ω    -34.00  25.00   0.50    0.06    --  -47.95  37.00-150.00  118
 25  ω   -122.00 -35.00   0.50    0.06    --  -47.95 -29.00 -82.00  174
 26  ω   -120.00 -73.00   0.50    0.06    --  -47.95-125.00  30.00   94
 27  ω   -120.00 -64.00   0.50    0.06    --  -47.95 -77.00  60.00  112
 28  ω   -161.00 -74.00   0.50    0.25    --  -86.25 -29.00 -82.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2068081000
_diffrn_orient_matrix_UB_12      0.0310645000
_diffrn_orient_matrix_UB_13      0.0693512000
_diffrn_orient_matrix_UB_21      -0.3274410000
_diffrn_orient_matrix_UB_22      -0.0008591000
_diffrn_orient_matrix_UB_23      0.0467632000
_diffrn_orient_matrix_UB_31      0.0880137000
_diffrn_orient_matrix_UB_32      -0.0760387000
_diffrn_orient_matrix_UB_33      0.0277651000
_diffrn_oxdiff_digest_frames     
;
01127b13eb444f30c7dc3e5dbefd6e25af0010179b9
;
_diffrn_oxdiff_digest_hkl        
;
01088e8dc8b49cf33a314fe9075a889eebf5d3
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2431
_reflns_number_total             2654
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+0.8889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0736
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br1 Br 0.34490(7) 0.40924(2) 0.76594(2) 0.01867(10) Uani 1 1 d . . . . .
Br2 Br 0.10561(7) 0.47745(2) 0.61195(2) 0.01724(10) Uani 1 1 d . . . . .
O1 O 0.6748(5) 0.27231(10) 0.72542(11) 0.0195(4) Uani 1 1 d . . . . .
C1 C 0.4729(7) 0.26918(13) 0.67009(14) 0.0147(5) Uani 1 1 d . . . . .
C2 C 0.3707(6) 0.33430(13) 0.62323(14) 0.0138(5) Uani 1 1 d . . . . .
C3 C 0.3061(7) 0.32197(13) 0.54037(15) 0.0147(5) Uani 1 1 d . . . . .
C4 C 0.3769(7) 0.37223(13) 0.48475(15) 0.0160(5) Uani 1 1 d . . . . .
H4 H 0.487318 0.415695 0.499169 0.019 Uiso 1 1 calc R . . . .
C5 C 0.2865(7) 0.35924(14) 0.40742(15) 0.0178(5) Uani 1 1 d . . . . .
H5 H 0.343154 0.393358 0.369838 0.021 Uiso 1 1 calc R . . . .
C6 C 0.1169(7) 0.29768(14) 0.38546(15) 0.0178(5) Uani 1 1 d . . . . .
H6 H 0.039713 0.291156 0.333683 0.021 Uiso 1 1 calc R . . . .
C7 C 0.0580(6) 0.24416(14) 0.44032(15) 0.0162(5) Uani 1 1 d . . . . .
C8 C -0.1072(7) 0.17831(15) 0.41797(16) 0.0197(5) Uani 1 1 d . . . . .
H8 H -0.194473 0.172260 0.366830 0.024 Uiso 1 1 calc R . . . .
C9 C -0.1396(7) 0.12468(14) 0.46939(17) 0.0212(6) Uani 1 1 d . . . . .
H9 H -0.255532 0.082079 0.454049 0.025 Uiso 1 1 calc R . . . .
C10 C -0.0021(7) 0.13126(14) 0.54625(16) 0.0189(5) Uani 1 1 d . . . . .
C11 C -0.0020(8) 0.07372(14) 0.59887(18) 0.0225(6) Uani 1 1 d . . . . .
H11 H -0.111032 0.030176 0.584220 0.027 Uiso 1 1 calc R . . . .
C12 C 0.1527(8) 0.07981(14) 0.67053(18) 0.0231(6) Uani 1 1 d . . . . .
H12 H 0.150838 0.040614 0.704909 0.028 Uiso 1 1 calc R . . . .
C13 C 0.3129(7) 0.14359(14) 0.69299(16) 0.0198(5) Uani 1 1 d . . . . .
H13 H 0.426057 0.147109 0.742067 0.024 Uiso 1 1 calc R . . . .
C14 C 0.3078(7) 0.20164(13) 0.64421(15) 0.0161(5) Uani 1 1 d . . . . .
C15 C 0.1492(7) 0.19682(13) 0.57043(15) 0.0154(5) Uani 1 1 d . . . . .
C16 C 0.1684(6) 0.25513(13) 0.51706(15) 0.0142(5) Uani 1 1 d . . . . .
C17 C 0.3011(7) 0.39505(14) 0.65943(15) 0.0155(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
Br1 C17 1.883(3) . ?
Br2 C17 1.898(3) . ?
O1 C1 1.221(3) . ?
C1 C2 1.514(3) . ?
C1 C14 1.482(4) . ?
C2 C3 1.479(4) . ?
C2 C17 1.337(4) . ?
C3 C4 1.391(4) . ?
C3 C16 1.416(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.405(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.376(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.414(4) . ?
C7 C8 1.438(4) . ?
C7 C16 1.407(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.359(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.431(4) . ?
C10 C11 1.418(4) . ?
C10 C15 1.419(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.372(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.397(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(4) . ?
C14 C15 1.409(4) . ?
C15 C16 1.442(4) . ?

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 C2 122.4(2) . . ?
O1 C1 C14 122.6(2) . . ?
C14 C1 C2 115.1(2) . . ?
C3 C2 C1 115.7(2) . . ?
C17 C2 C1 119.0(2) . . ?
C17 C2 C3 124.6(2) . . ?
C4 C3 C2 123.3(2) . . ?
C4 C3 C16 118.8(2) . . ?
C16 C3 C2 117.8(2) . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.7(2) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C8 120.5(2) . . ?
C16 C7 C6 119.5(2) . . ?
C16 C7 C8 120.0(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.1(2) . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 122.3(3) . . ?
C11 C10 C15 118.5(3) . . ?
C15 C10 C9 119.2(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.1(3) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C1 119.3(3) . . ?
C13 C14 C15 120.6(3) . . ?
C15 C14 C1 120.1(2) . . ?
C10 C15 C16 119.7(2) . . ?
C14 C15 C10 119.2(2) . . ?
C14 C15 C16 120.8(2) . . ?
C3 C16 C15 120.9(2) . . ?
C7 C16 C3 120.0(2) . . ?
C7 C16 C15 119.0(2) . . ?
Br1 C17 Br2 109.62(13) . . ?
C2 C17 Br1 125.3(2) . . ?
C2 C17 Br2 124.9(2) . . ?

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 C1 C2 C3 145.7(2) . . . . ?
O1 C1 C2 C17 -43.1(4) . . . . ?
O1 C1 C14 C13 15.8(4) . . . . ?
O1 C1 C14 C15 -163.8(2) . . . . ?
C1 C2 C3 C4 -147.1(2) . . . . ?
C1 C2 C3 C16 32.2(3) . . . . ?
C1 C2 C17 Br1 4.0(4) . . . . ?
C1 C2 C17 Br2 -170.33(18) . . . . ?
C1 C14 C15 C10 178.9(2) . . . . ?
C1 C14 C15 C16 5.0(4) . . . . ?
C2 C1 C14 C13 -163.7(2) . . . . ?
C2 C1 C14 C15 16.6(3) . . . . ?
C2 C3 C4 C5 -175.4(2) . . . . ?
C2 C3 C16 C7 171.2(2) . . . . ?
C2 C3 C16 C15 -10.8(4) . . . . ?
C3 C2 C17 Br1 174.35(19) . . . . ?
C3 C2 C17 Br2 0.0(4) . . . . ?
C3 C4 C5 C6 2.0(4) . . . . ?
C4 C3 C16 C7 -9.4(4) . . . . ?
C4 C3 C16 C15 168.6(2) . . . . ?
C4 C5 C6 C7 -5.3(4) . . . . ?
C5 C6 C7 C8 -177.6(2) . . . . ?
C5 C6 C7 C16 1.1(4) . . . . ?
C6 C7 C8 C9 174.8(2) . . . . ?
C6 C7 C16 C3 6.2(4) . . . . ?
C6 C7 C16 C15 -171.8(2) . . . . ?
C7 C8 C9 C10 -1.9(4) . . . . ?
C8 C7 C16 C3 -175.0(2) . . . . ?
C8 C7 C16 C15 7.0(4) . . . . ?
C8 C9 C10 C11 -173.6(3) . . . . ?
C8 C9 C10 C15 4.4(4) . . . . ?
C9 C10 C11 C12 175.4(3) . . . . ?
C9 C10 C15 C14 -175.2(2) . . . . ?
C9 C10 C15 C16 -1.2(4) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C10 C15 C16 C3 177.6(2) . . . . ?
C10 C15 C16 C7 -4.4(4) . . . . ?
C11 C10 C15 C14 2.9(4) . . . . ?
C11 C10 C15 C16 176.9(2) . . . . ?
C11 C12 C13 C14 2.0(4) . . . . ?
C12 C13 C14 C1 178.6(2) . . . . ?
C12 C13 C14 C15 -1.7(4) . . . . ?
C13 C14 C15 C10 -0.8(4) . . . . ?
C13 C14 C15 C16 -174.7(2) . . . . ?
C14 C1 C2 C3 -34.7(3) . . . . ?
C14 C1 C2 C17 136.5(3) . . . . ?
C14 C15 C16 C3 -8.5(4) . . . . ?
C14 C15 C16 C7 169.5(2) . . . . ?
C15 C10 C11 C12 -2.7(4) . . . . ?
C16 C3 C4 C5 5.3(4) . . . . ?
C16 C7 C8 C9 -4.0(4) . . . . ?
C17 C2 C3 C4 42.3(4) . . . . ?
C17 C2 C3 C16 -138.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.579
_oxdiff_exptl_absorpt_empirical_full_min 0.564
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/DCM'
####################################################################### 
# 
# 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_fs67-2
_database_code_depnum_ccdc_archive 'CCDC 2009232'
loop_
_audit_author_name
_audit_author_address
'Jian-Bin Lin'
;Memorial University of Newfoundland
Canada
;
_audit_update_record             
;
2020-06-11 deposited with the CCDC.	2020-09-25 downloaded from the CCDC.
;
_audit_creation_date             2020-02-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'ethyl 5-hydroxypyrene-4-carboxylate'
_chemical_formula_moiety         'C19 H14 O3'
_chemical_formula_sum            'C19 H14 O3'
_chemical_formula_weight         290.30
_chemical_melting_point          '. 125.5 -126.2'
_chemical_oxdiff_formula         C17H8Br2O
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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.9879(7)
_cell_length_b                   4.96700(10)
_cell_length_c                   18.9991(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.932(4)
_cell_angle_gamma                90
_cell_volume                     1360.06(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4836
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7690
_cell_measurement_theta_min      4.8400
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.861
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17708
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.407
_diffrn_reflns_theta_min         3.066
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00 120.00   0.50    0.40    --   47.70  44.00  11.00  170
  2  ω     94.00 178.00   0.50    2.50    --  107.75  44.00  11.00  168
  3  ω     95.00 178.00   0.50    2.50    --  107.75  30.00 -60.00  166
  4  ω     95.00 178.00   0.50    2.50    --  107.75 125.00 -90.00  166
  5  ω     95.00 178.00   0.50    2.50    --  107.75 125.00-120.00  166
  6  ω     91.00 178.00   0.50    2.50    --  107.75  61.00 -90.00  174
  7  ω     95.00 178.00   0.50    2.50    --  107.75  45.00 150.00  166
  8  ω     35.00  79.00   0.50    2.50    --  107.75 -61.00 -90.00   88
  9  ω     35.00  79.00   0.50    2.50    --  107.75 -61.00-150.00   88
 10  ω     35.00 106.00   0.50    2.50    --  107.75 -94.00-120.00  142
 11  ω     35.00  79.00   0.50    2.50    --  107.75 -61.00-120.00   88
 12  ω     35.00  79.00   0.50    2.50    --  107.75 -61.00 -60.00   88
 13  ω     35.00  79.00   0.50    2.50    --  107.75 -61.00 -30.00   88
 14  ω     35.00 131.00   0.50    2.50    --  107.75 -77.00  30.00  192
 15  ω     35.00 112.00   0.50    2.50    --  107.75-125.00  90.00  154
 16  ω     35.00  79.00   0.50    2.50    --  107.75 -61.00  60.00   88
 17  ω     35.00  79.00   0.50    2.50    --  107.75 -61.00  90.00   88
 18  ω     35.00  79.00   0.50    2.50    --  107.75 -61.00  30.00   88
 19  ω     35.00 112.00   0.50    2.50    --  107.75-125.00 120.00  154
 20  ω    -24.00  56.00   0.50    0.40    --   47.70 -44.00-139.00  160
 21  ω    -16.00  28.00   0.50    0.40    --  -47.70  19.00-120.00   88
 22  ω    -42.00 -14.00   0.50    2.50    --  -86.25  44.00  11.00   56
 23  ω    -42.00  24.00   0.50    0.40    --  -47.70  44.00  11.00  132
 24  ω    -16.00  28.00   0.50    0.40    --  -47.70  19.00 150.00   88
 25  ω     25.00 120.00   0.50    0.40    --   47.70  77.00  90.00  190
 26  ω    -43.00 -14.00   0.50    2.50    --  -86.25  45.00-180.00   58
 27  ω   -120.00 -34.00   0.50    0.40    --  -47.70 -44.00-139.00  172
 28  ω   -119.00 -25.00   0.50    0.40    --  -47.70 -77.00 150.00  188
 29  ω   -119.00 -63.00   0.50    0.40    --  -47.70 -77.00 -30.00  112
 30  ω   -158.00 -73.00   0.50    2.50    --  -86.25 -44.00-139.00  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0336278000
_diffrn_orient_matrix_UB_12      0.0732744000
_diffrn_orient_matrix_UB_13      0.0672774000
_diffrn_orient_matrix_UB_21      -0.0913289000
_diffrn_orient_matrix_UB_22      -0.1527196000
_diffrn_orient_matrix_UB_23      -0.0332833000
_diffrn_orient_matrix_UB_31      0.0441689000
_diffrn_orient_matrix_UB_32      -0.2597757000
_diffrn_orient_matrix_UB_33      0.0384956000
_diffrn_oxdiff_digest_frames     
;
019d8280c87b9a069fafd165e4f3d2bf1c00035bd46
;
_diffrn_oxdiff_digest_hkl        
;
01179635682d186d4176bd21f2c12fff3f55ee
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2471
_reflns_number_total             2855
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2855
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.081
_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)+(0.0994P)²+1.0688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1896
_refine_ls_wR_factor_ref         0.1968
_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 C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.63892(11) 0.9695(3) 0.67817(8) 0.0369(4) Uani 1 1 d . . . . .
H1 H 0.607454 1.083155 0.648937 0.055 Uiso 1 1 calc GR . . . .
O2 O 0.58362(11) 1.2293(3) 0.56351(8) 0.0381(4) Uani 1 1 d . . . . .
O3 O 0.62891(11) 1.1347(3) 0.46427(8) 0.0341(4) Uani 1 1 d . . . . .
C1 C 0.69275(15) 0.8324(4) 0.64511(11) 0.0315(5) Uani 1 1 d . . . . .
C2 C 0.69588(14) 0.8822(4) 0.57360(10) 0.0286(4) Uani 1 1 d . . . . .
C3 C 0.75954(14) 0.7278(4) 0.54327(11) 0.0304(5) Uani 1 1 d . . . . .
C4 C 0.77128(16) 0.7678(4) 0.47326(11) 0.0333(5) Uani 1 1 d . . . . .
H4 H 0.735601 0.901826 0.442301 0.040 Uiso 1 1 calc R . . . .
C5 C 0.83414(16) 0.6150(4) 0.44834(12) 0.0353(5) Uani 1 1 d . . . . .
H5 H 0.840664 0.647904 0.400742 0.042 Uiso 1 1 calc R . . . .
C6 C 0.88726(16) 0.4170(4) 0.49087(12) 0.0344(5) Uani 1 1 d . . . . .
H6 H 0.928942 0.312969 0.472311 0.041 Uiso 1 1 calc R . . . .
C7 C 0.87941(15) 0.3703(4) 0.56147(12) 0.0328(5) Uani 1 1 d . . . . .
C8 C 0.93480(16) 0.1696(4) 0.60740(12) 0.0361(5) Uani 1 1 d . . . . .
H8 H 0.977444 0.067377 0.589428 0.043 Uiso 1 1 calc R . . . .
C9 C 0.92787(15) 0.1216(4) 0.67622(12) 0.0340(5) Uani 1 1 d . . . . .
H9 H 0.965073 -0.014372 0.705259 0.041 Uiso 1 1 calc R . . . .
C10 C 0.86549(15) 0.2729(4) 0.70512(11) 0.0334(5) Uani 1 1 d . . . . .
C11 C 0.85768(16) 0.2306(4) 0.77609(12) 0.0362(5) Uani 1 1 d . . . . .
H11 H 0.894659 0.096571 0.806115 0.043 Uiso 1 1 calc R . . . .
C12 C 0.79672(17) 0.3818(4) 0.80297(12) 0.0377(5) Uani 1 1 d . . . . .
H12 H 0.792317 0.349068 0.851172 0.045 Uiso 1 1 calc R . . . .
C13 C 0.74255(16) 0.5780(5) 0.76135(11) 0.0361(5) Uani 1 1 d . . . . .
H13 H 0.701357 0.680657 0.780785 0.043 Uiso 1 1 calc R . . . .
C14 C 0.74825(15) 0.6267(4) 0.68967(11) 0.0318(5) Uani 1 1 d . . . . .
C15 C 0.80893(14) 0.4764(4) 0.66072(10) 0.0291(4) Uani 1 1 d . . . . .
C16 C 0.81611(14) 0.5234(4) 0.58835(11) 0.0297(4) Uani 1 1 d . . . . .
C17 C 0.63275(15) 1.0948(4) 0.53448(11) 0.0315(5) Uani 1 1 d . . . . .
C18 C 0.56483(16) 1.3450(4) 0.42697(12) 0.0374(5) Uani 1 1 d . . . . .
H18A H 0.582530 1.520931 0.451282 0.045 Uiso 1 1 calc R . . . .
H18B H 0.500708 1.301933 0.427998 0.045 Uiso 1 1 calc R . . . .
C19 C 0.57103(19) 1.3549(6) 0.34922(13) 0.0477(6) Uani 1 1 d . . . . .
H19A H 0.529654 1.495747 0.322371 0.072 Uiso 1 1 calc GR . . . .
H19B H 0.552462 1.180488 0.325634 0.072 Uiso 1 1 calc GR . . . .
H19C H 0.634999 1.394968 0.349067 0.072 Uiso 1 1 calc GR . . . .


_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 H1 0.8400 . ?
O1 C1 1.337(2) . ?
O2 C17 1.231(3) . ?
O3 C17 1.334(2) . ?
O3 C18 1.464(3) . ?
C1 C2 1.394(3) . ?
C1 C14 1.437(3) . ?
C2 C3 1.460(3) . ?
C2 C17 1.475(3) . ?
C3 C4 1.403(3) . ?
C3 C16 1.444(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.379(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.398(3) . ?
C7 C8 1.431(3) . ?
C7 C16 1.416(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.361(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.422(3) . ?
C10 C11 1.401(3) . ?
C10 C15 1.435(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.372(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.409(3) . ?
C14 C15 1.401(3) . ?
C15 C16 1.427(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.506(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C1 O1 H1 109.5 . . ?
C17 O3 C18 115.64(16) . . ?
O1 C1 C2 123.60(19) . . ?
O1 C1 C14 114.31(18) . . ?
C2 C1 C14 122.09(19) . . ?
C1 C2 C3 119.45(18) . . ?
C1 C2 C17 115.43(18) . . ?
C3 C2 C17 125.12(17) . . ?
C4 C3 C2 124.43(19) . . ?
C4 C3 C16 117.12(19) . . ?
C16 C3 C2 118.43(17) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.3(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.74(19) . . ?
C6 C5 H5 119.1 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.6(2) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C8 120.9(2) . . ?
C6 C7 C16 119.9(2) . . ?
C16 C7 C8 119.22(19) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.6(2) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.67(19) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C15 119.35(19) . . ?
C11 C10 C9 122.0(2) . . ?
C11 C10 C15 118.7(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.3(2) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C1 120.8(2) . . ?
C15 C14 C1 118.73(18) . . ?
C15 C14 C13 120.4(2) . . ?
C14 C15 C10 119.14(18) . . ?
C14 C15 C16 121.33(19) . . ?
C16 C15 C10 119.53(19) . . ?
C7 C16 C3 120.40(18) . . ?
C7 C16 C15 119.65(19) . . ?
C15 C16 C3 119.94(19) . . ?
O2 C17 O3 120.01(19) . . ?
O2 C17 C2 122.86(18) . . ?
O3 C17 C2 117.11(17) . . ?
O3 C18 H18A 110.4 . . ?
O3 C18 H18B 110.4 . . ?
O3 C18 C19 106.82(18) . . ?
H18A C18 H18B 108.6 . . ?
C19 C18 H18A 110.4 . . ?
C19 C18 H18B 110.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
_geom_hbond_publ_flag
O1 H1 O2 0.84 1.72 2.471(2) 147.1 . yes

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.660
_oxdiff_exptl_absorpt_empirical_full_min 0.728
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/DCM'
