# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1883650'
loop_
_audit_author_name
_audit_author_address
'Shigeki Mori'
;Ehime Univeristy
Japan
;
_audit_update_record             
;
2018-12-07 deposited with the CCDC.	2019-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H24 O2'
_chemical_formula_sum            'C27 H24 O2'
_chemical_formula_weight         380.46

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'

_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                   9.9833(2)
_cell_length_b                   11.7354(2)
_cell_length_c                   34.8372(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.4542(19)
_cell_angle_gamma                90
_cell_volume                     4046.96(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    37664
_cell_measurement_theta_min      2.02
_cell_measurement_theta_max      31.30

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             1616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku Varimax with Saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            68205
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         1.833
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9788
_reflns_number_gt                7792
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3.1 (Rigaku, 2018)'
_computing_publication_material  'CrystalStructure 4.3.1 (Rigaku, 2018)'
_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)+(0.0479P)²+1.8408P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9788
_refine_ls_number_parameters     529
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.43785(10) 0.38426(9) 0.67785(3) 0.0221(2) Uani 1 1 d . . . . .
O2 O 0.37342(10) 0.27339(8) 0.62633(3) 0.0198(2) Uani 1 1 d . . . . .
O3 O 0.85280(14) 0.29164(11) 0.67732(3) 0.0375(3) Uani 1 1 d . . . . .
O4 O 0.90480(10) 0.28199(9) 0.61703(3) 0.0207(2) Uani 1 1 d . . . . .
C1 C 0.25640(13) 0.44410(11) 0.63046(4) 0.0138(3) Uani 1 1 d . . . . .
C2 C 0.17494(13) 0.43233(11) 0.59358(4) 0.0137(3) Uani 1 1 d . . . . .
C3 C 0.06595(13) 0.50711(11) 0.59226(4) 0.0151(3) Uani 1 1 d . . . . .
H3 H -0.003389 0.515312 0.571028 0.018 Uiso 1 1 calc R U . . .
C4 C 0.07426(13) 0.56844(11) 0.62707(4) 0.0141(3) Uani 1 1 d . . . . .
C5 C -0.02161(14) 0.64522(11) 0.63667(4) 0.0157(3) Uani 1 1 d . . . . .
H5 H -0.097958 0.655878 0.617705 0.019 Uiso 1 1 calc R U . . .
C6 C -0.02065(14) 0.70878(12) 0.67047(4) 0.0176(3) Uani 1 1 d . . . . .
H6 H -0.099275 0.753102 0.672197 0.021 Uiso 1 1 calc R U . . .
C7 C 0.07963(14) 0.71623(12) 0.70203(4) 0.0177(3) Uani 1 1 d . . . . .
H7 H 0.060385 0.767733 0.721631 0.021 Uiso 1 1 calc R U . . .
C8 C 0.20421(14) 0.66054(11) 0.70976(4) 0.0154(3) Uani 1 1 d . . . . .
C9 C 0.25336(14) 0.57523(11) 0.68723(4) 0.0148(3) Uani 1 1 d . . . . .
H9 H 0.336861 0.542441 0.697990 0.018 Uiso 1 1 calc R U . . .
C10 C 0.19884(13) 0.53087(11) 0.65145(4) 0.0137(3) Uani 1 1 d . . . . .
C11 C 0.36537(13) 0.36910(11) 0.64769(4) 0.0138(3) Uani 1 1 d . . . . .
C12 C 0.48159(15) 0.19656(12) 0.63960(4) 0.0192(3) Uani 1 1 d . . . . .
H12A H 0.456282 0.150584 0.661018 0.023 Uiso 1 1 calc R U . . .
H12B H 0.563322 0.240325 0.648527 0.023 Uiso 1 1 calc R U . . .
H12C H 0.498968 0.146343 0.618321 0.023 Uiso 1 1 calc R U . . .
C13 C 0.19835(13) 0.36009(11) 0.56022(4) 0.0136(3) Uani 1 1 d . . . . .
C14 C 0.32600(14) 0.34988(11) 0.54808(4) 0.0142(3) Uani 1 1 d . . . . .
H14 H 0.401358 0.386647 0.562363 0.017 Uiso 1 1 calc R U . . .
C15 C 0.34395(14) 0.28689(11) 0.51553(4) 0.0144(3) Uani 1 1 d . . . . .
H15 H 0.431350 0.281875 0.507647 0.017 Uiso 1 1 calc R U . . .
C16 C 0.23520(13) 0.23027(11) 0.49397(4) 0.0132(3) Uani 1 1 d . . . . .
C17 C 0.10785(14) 0.24110(12) 0.50616(4) 0.0157(3) Uani 1 1 d . . . . .
H17 H 0.032647 0.203572 0.492087 0.019 Uiso 1 1 calc R U . . .
C18 C 0.08905(14) 0.30559(12) 0.53843(4) 0.0154(3) Uani 1 1 d . . . . .
H18 H 0.001122 0.312840 0.545806 0.019 Uiso 1 1 calc R U . . .
C19 C 0.25492(14) 0.16133(11) 0.45927(4) 0.0140(3) Uani 1 1 d . . . . .
C20 C 0.38092(14) 0.11401(12) 0.45508(4) 0.0163(3) Uani 1 1 d . . . . .
H20 H 0.454913 0.125899 0.474731 0.020 Uiso 1 1 calc R U . . .
C21 C 0.39954(15) 0.04981(12) 0.42258(4) 0.0191(3) Uani 1 1 d . . . . .
H21 H 0.485877 0.018686 0.420143 0.023 Uiso 1 1 calc R U . . .
C22 C 0.29251(15) 0.03126(12) 0.39382(4) 0.0197(3) Uani 1 1 d . . . . .
H22 H 0.304972 -0.012807 0.371687 0.024 Uiso 1 1 calc R U . . .
C23 C 0.16701(15) 0.07738(12) 0.39753(4) 0.0196(3) Uani 1 1 d . . . . .
H23 H 0.093387 0.064840 0.377815 0.024 Uiso 1 1 calc R U . . .
C24 C 0.14807(14) 0.14181(12) 0.42985(4) 0.0176(3) Uani 1 1 d . . . . .
H24 H 0.061529 0.172975 0.432000 0.021 Uiso 1 1 calc R U . . .
C25 C 0.29369(15) 0.69176(12) 0.74728(4) 0.0188(3) Uani 1 1 d . . . . .
H25 H 0.381683 0.651031 0.747307 0.023 Uiso 1 1 calc R U . . .
C26 C 0.23070(17) 0.65086(15) 0.78251(4) 0.0293(4) Uani 1 1 d . . . . .
H26A H 0.145439 0.691257 0.783736 0.035 Uiso 1 1 calc R U . . .
H26B H 0.292872 0.666320 0.806089 0.035 Uiso 1 1 calc R U . . .
H26C H 0.213372 0.568773 0.780327 0.035 Uiso 1 1 calc R U . . .
C27 C 0.32414(16) 0.81973(13) 0.75043(5) 0.0265(3) Uani 1 1 d . . . . .
H27A H 0.391909 0.833901 0.772897 0.032 Uiso 1 1 calc R U . . .
H27B H 0.241124 0.861349 0.753542 0.032 Uiso 1 1 calc R U . . .
H27C H 0.358855 0.845742 0.726878 0.032 Uiso 1 1 calc R U . . .
C28 C 0.74446(13) 0.41675(11) 0.62872(4) 0.0139(3) Uani 1 1 d . . . . .
C29 C 0.70058(13) 0.44295(11) 0.58910(4) 0.0142(3) Uani 1 1 d . . . . .
C30 C 0.63309(14) 0.54810(12) 0.58742(4) 0.0163(3) Uani 1 1 d . . . . .
H30 H 0.594656 0.585161 0.564342 0.020 Uiso 1 1 calc R U . . .
C31 C 0.63109(13) 0.59002(11) 0.62500(4) 0.0149(3) Uani 1 1 d . . . . .
C32 C 0.57756(14) 0.69443(12) 0.63433(4) 0.0188(3) Uani 1 1 d . . . . .
H32 H 0.538471 0.739153 0.613046 0.023 Uiso 1 1 calc R U . . .
C33 C 0.57388(15) 0.74174(12) 0.67076(4) 0.0208(3) Uani 1 1 d . . . . .
H33 H 0.535399 0.815754 0.670904 0.025 Uiso 1 1 calc R U . . .
C34 C 0.61855(15) 0.69611(12) 0.70706(4) 0.0199(3) Uani 1 1 d . . . . .
H34 H 0.604484 0.743593 0.728259 0.024 Uiso 1 1 calc R U . . .
C35 C 0.68064(14) 0.59196(12) 0.71740(4) 0.0178(3) Uani 1 1 d . . . . .
C36 C 0.71836(14) 0.50906(12) 0.69211(4) 0.0166(3) Uani 1 1 d . . . . .
H36 H 0.763718 0.444989 0.704367 0.020 Uiso 1 1 calc R U . . .
C37 C 0.70018(13) 0.50526(11) 0.65190(4) 0.0142(3) Uani 1 1 d . . . . .
C38 C 0.83608(14) 0.32518(12) 0.64423(4) 0.0160(3) Uani 1 1 d . . . . .
C39 C 0.99818(15) 0.19145(13) 0.62799(4) 0.0223(3) Uani 1 1 d . . . . .
H39A H 0.971411 0.151405 0.650482 0.027 Uiso 1 1 calc R U . . .
H39B H 1.089119 0.223030 0.634624 0.027 Uiso 1 1 calc R U . . .
H39C H 0.997916 0.137979 0.606378 0.027 Uiso 1 1 calc R U . . .
C40 C 0.71378(13) 0.37333(11) 0.55451(4) 0.0139(3) Uani 1 1 d . . . . .
C41 C 0.69735(13) 0.25484(12) 0.55451(4) 0.0149(3) Uani 1 1 d . . . . .
H41 H 0.677952 0.217874 0.577415 0.018 Uiso 1 1 calc R U . . .
C42 C 0.70881(13) 0.19057(12) 0.52182(4) 0.0155(3) Uani 1 1 d . . . . .
H42 H 0.697245 0.110307 0.522712 0.019 Uiso 1 1 calc R U . . .
C43 C 0.73718(13) 0.24165(11) 0.48739(4) 0.0136(3) Uani 1 1 d . . . . .
C44 C 0.75185(14) 0.36021(12) 0.48731(4) 0.0163(3) Uani 1 1 d . . . . .
H44 H 0.770312 0.397360 0.464341 0.020 Uiso 1 1 calc R U . . .
C45 C 0.73998(14) 0.42459(12) 0.52006(4) 0.0165(3) Uani 1 1 d . . . . .
H45 H 0.749841 0.505016 0.519066 0.020 Uiso 1 1 calc R U . . .
C46 C 0.75052(13) 0.17155(12) 0.45237(4) 0.0140(3) Uani 1 1 d . . . . .
C47 C 0.77342(14) 0.05373(12) 0.45521(4) 0.0184(3) Uani 1 1 d . . . . .
H47 H 0.783158 0.018514 0.479970 0.022 Uiso 1 1 calc R U . . .
C48 C 0.78216(15) -0.01242(13) 0.42265(4) 0.0214(3) Uani 1 1 d . . . . .
H48 H 0.795762 -0.092325 0.425194 0.026 Uiso 1 1 calc R U . . .
C49 C 0.77103(14) 0.03806(13) 0.38629(4) 0.0201(3) Uani 1 1 d . . . . .
H49 H 0.777014 -0.007029 0.363929 0.024 Uiso 1 1 calc R U . . .
C50 C 0.75106(14) 0.15504(13) 0.38289(4) 0.0187(3) Uani 1 1 d . . . . .
H50 H 0.745206 0.190219 0.358170 0.022 Uiso 1 1 calc R U . . .
C51 C 0.73963(14) 0.22074(12) 0.41548(4) 0.0163(3) Uani 1 1 d . . . . .
H51 H 0.724166 0.300362 0.412684 0.020 Uiso 1 1 calc R U . . .
C52 C 0.71036(16) 0.56508(13) 0.76063(4) 0.0226(3) Uani 1 1 d . . . . .
H52 H 0.683319 0.632965 0.775179 0.027 Uiso 1 1 calc R U . . .
C53 C 0.62636(16) 0.46358(14) 0.77134(5) 0.0262(3) Uani 1 1 d . . . . .
H53A H 0.642308 0.451391 0.799386 0.031 Uiso 1 1 calc R U . . .
H53B H 0.652678 0.395162 0.758025 0.031 Uiso 1 1 calc R U . . .
H53C H 0.530298 0.479205 0.763450 0.031 Uiso 1 1 calc R U . . .
C54 C 0.86067(18) 0.54409(17) 0.77312(5) 0.0348(4) Uani 1 1 d . . . . .
H54A H 0.876060 0.529061 0.801011 0.042 Uiso 1 1 calc R U . . .
H54B H 0.912202 0.611533 0.767242 0.042 Uiso 1 1 calc R U . . .
H54C H 0.890190 0.478193 0.759104 0.042 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.2091(16) . ?
O2 C11 1.3555(16) . ?
O2 C12 1.4365(16) . ?
O3 C38 1.2088(17) . ?
O4 C38 1.3395(17) . ?
O4 C39 1.4323(17) . ?
C1 C10 1.4181(18) . ?
C1 C2 1.4353(18) . ?
C1 C11 1.4660(19) . ?
C2 C3 1.3941(19) . ?
C2 C13 1.4812(18) . ?
C3 C4 1.4034(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3867(19) . ?
C4 C10 1.4794(18) . ?
C5 C6 1.3928(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.400(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.3996(19) . ?
C8 C25 1.5289(19) . ?
C9 C10 1.3946(18) . ?
C9 H9 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.3989(19) . ?
C13 C18 1.4004(19) . ?
C14 C15 1.3847(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.4046(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.3976(19) . ?
C16 C19 1.4887(18) . ?
C17 C18 1.3878(19) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.3989(19) . ?
C19 C20 1.3998(19) . ?
C20 C21 1.3925(19) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.3896(19) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.527(2) . ?
C25 C27 1.533(2) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C37 1.4211(18) . ?
C28 C29 1.4264(18) . ?
C28 C38 1.4681(19) . ?
C29 C30 1.4036(19) . ?
C29 C40 1.4757(18) . ?
C30 C31 1.4012(19) . ?
C30 H30 0.9500 . ?
C31 C32 1.3921(19) . ?
C31 C37 1.4750(18) . ?
C32 C33 1.390(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.392(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.396(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.3965(19) . ?
C35 C52 1.530(2) . ?
C36 C37 1.3898(19) . ?
C36 H36 0.9500 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 C45 1.3972(19) . ?
C40 C41 1.4001(19) . ?
C41 C42 1.3829(19) . ?
C41 H41 0.9500 . ?
C42 C43 1.4025(18) . ?
C42 H42 0.9500 . ?
C43 C44 1.3991(19) . ?
C43 C46 1.4916(18) . ?
C44 C45 1.3864(19) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 C51 1.4003(18) . ?
C46 C47 1.4028(19) . ?
C47 C48 1.387(2) . ?
C47 H47 0.9500 . ?
C48 C49 1.390(2) . ?
C48 H48 0.9500 . ?
C49 C50 1.390(2) . ?
C49 H49 0.9500 . ?
C50 C51 1.3891(19) . ?
C50 H50 0.9500 . ?
C51 H51 0.9500 . ?
C52 C54 1.527(2) . ?
C52 C53 1.530(2) . ?
C52 H52 1.0000 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 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
C11 O2 C12 116.04(11) . . ?
C38 O4 C39 117.87(11) . . ?
C10 C1 C2 108.08(12) . . ?
C10 C1 C11 123.28(12) . . ?
C2 C1 C11 127.80(12) . . ?
C3 C2 C1 108.55(12) . . ?
C3 C2 C13 122.43(12) . . ?
C1 C2 C13 128.95(12) . . ?
C2 C3 C4 109.63(12) . . ?
C2 C3 H3 125.2 . . ?
C4 C3 H3 125.2 . . ?
C5 C4 C3 125.20(12) . . ?
C5 C4 C10 127.61(12) . . ?
C3 C4 C10 107.13(11) . . ?
C4 C5 C6 128.51(13) . . ?
C4 C5 H5 115.7 . . ?
C6 C5 H5 115.7 . . ?
C7 C6 C5 128.86(13) . . ?
C7 C6 H6 115.6 . . ?
C5 C6 H6 115.6 . . ?
C6 C7 C8 130.80(13) . . ?
C6 C7 H7 114.6 . . ?
C8 C7 H7 114.6 . . ?
C9 C8 C7 126.40(13) . . ?
C9 C8 C25 116.25(12) . . ?
C7 C8 C25 117.29(12) . . ?
C10 C9 C8 130.07(13) . . ?
C10 C9 H9 115.0 . . ?
C8 C9 H9 115.0 . . ?
C9 C10 C1 126.28(12) . . ?
C9 C10 C4 127.12(12) . . ?
C1 C10 C4 106.53(11) . . ?
O1 C11 O2 121.85(12) . . ?
O1 C11 C1 126.60(13) . . ?
O2 C11 C1 111.49(11) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 118.25(12) . . ?
C14 C13 C2 121.92(12) . . ?
C18 C13 C2 119.71(12) . . ?
C15 C14 C13 120.87(12) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 121.16(12) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 117.70(12) . . ?
C17 C16 C19 121.17(12) . . ?
C15 C16 C19 121.13(12) . . ?
C18 C17 C16 121.31(12) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C13 120.70(13) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C24 C19 C20 117.96(12) . . ?
C24 C19 C16 121.01(12) . . ?
C20 C19 C16 121.03(12) . . ?
C21 C20 C19 121.06(13) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C20 120.12(13) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 119.57(13) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C22 C23 C24 120.50(13) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C19 120.78(13) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
C26 C25 C8 110.85(12) . . ?
C26 C25 C27 110.40(13) . . ?
C8 C25 C27 112.61(12) . . ?
C26 C25 H25 107.6 . . ?
C8 C25 H25 107.6 . . ?
C27 C25 H25 107.6 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C37 C28 C29 108.25(12) . . ?
C37 C28 C38 123.41(12) . . ?
C29 C28 C38 127.78(12) . . ?
C30 C29 C28 108.38(12) . . ?
C30 C29 C40 123.09(12) . . ?
C28 C29 C40 128.46(12) . . ?
C31 C30 C29 109.55(12) . . ?
C31 C30 H30 125.2 . . ?
C29 C30 H30 125.2 . . ?
C32 C31 C30 125.43(13) . . ?
C32 C31 C37 127.39(13) . . ?
C30 C31 C37 107.14(12) . . ?
C33 C32 C31 128.41(14) . . ?
C33 C32 H32 115.8 . . ?
C31 C32 H32 115.8 . . ?
C32 C33 C34 129.22(14) . . ?
C32 C33 H33 115.4 . . ?
C34 C33 H33 115.4 . . ?
C33 C34 C35 130.54(13) . . ?
C33 C34 H34 114.7 . . ?
C35 C34 H34 114.7 . . ?
C34 C35 C36 126.45(13) . . ?
C34 C35 C52 117.22(13) . . ?
C36 C35 C52 116.33(13) . . ?
C37 C36 C35 130.35(13) . . ?
C37 C36 H36 114.8 . . ?
C35 C36 H36 114.8 . . ?
C36 C37 C28 125.93(13) . . ?
C36 C37 C31 127.44(12) . . ?
C28 C37 C31 106.63(11) . . ?
O3 C38 O4 122.09(13) . . ?
O3 C38 C28 126.29(13) . . ?
O4 C38 C28 111.61(11) . . ?
O4 C39 H39A 109.5 . . ?
O4 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O4 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C45 C40 C41 117.56(12) . . ?
C45 C40 C29 120.62(12) . . ?
C41 C40 C29 121.80(12) . . ?
C42 C41 C40 121.29(12) . . ?
C42 C41 H41 119.4 . . ?
C40 C41 H41 119.4 . . ?
C41 C42 C43 121.25(13) . . ?
C41 C42 H42 119.4 . . ?
C43 C42 H42 119.4 . . ?
C44 C43 C42 117.36(12) . . ?
C44 C43 C46 121.77(12) . . ?
C42 C43 C46 120.88(12) . . ?
C45 C44 C43 121.35(13) . . ?
C45 C44 H44 119.3 . . ?
C43 C44 H44 119.3 . . ?
C44 C45 C40 121.18(13) . . ?
C44 C45 H45 119.4 . . ?
C40 C45 H45 119.4 . . ?
C51 C46 C47 117.62(12) . . ?
C51 C46 C43 121.25(12) . . ?
C47 C46 C43 121.13(12) . . ?
C48 C47 C46 121.40(13) . . ?
C48 C47 H47 119.3 . . ?
C46 C47 H47 119.3 . . ?
C47 C48 C49 120.06(13) . . ?
C47 C48 H48 120.0 . . ?
C49 C48 H48 120.0 . . ?
C48 C49 C50 119.49(13) . . ?
C48 C49 H49 120.3 . . ?
C50 C49 H49 120.3 . . ?
C51 C50 C49 120.31(13) . . ?
C51 C50 H50 119.8 . . ?
C49 C50 H50 119.8 . . ?
C50 C51 C46 121.09(13) . . ?
C50 C51 H51 119.5 . . ?
C46 C51 H51 119.5 . . ?
C54 C52 C35 111.81(12) . . ?
C54 C52 C53 110.75(14) . . ?
C35 C52 C53 110.98(12) . . ?
C54 C52 H52 107.7 . . ?
C35 C52 H52 107.7 . . ?
C53 C52 H52 107.7 . . ?
C52 C53 H53A 109.5 . . ?
C52 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C52 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C52 C54 H54A 109.5 . . ?
C52 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C52 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 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
C10 C1 C2 C3 -2.27(15) . . . . ?
C11 C1 C2 C3 167.42(13) . . . . ?
C10 C1 C2 C13 174.73(13) . . . . ?
C11 C1 C2 C13 -15.6(2) . . . . ?
C1 C2 C3 C4 0.58(15) . . . . ?
C13 C2 C3 C4 -176.65(12) . . . . ?
C2 C3 C4 C5 -175.89(13) . . . . ?
C2 C3 C4 C10 1.26(15) . . . . ?
C3 C4 C5 C6 179.85(14) . . . . ?
C10 C4 C5 C6 3.3(2) . . . . ?
C4 C5 C6 C7 4.1(2) . . . . ?
C5 C6 C7 C8 -2.6(3) . . . . ?
C6 C7 C8 C9 -4.7(3) . . . . ?
C6 C7 C8 C25 178.07(14) . . . . ?
C7 C8 C9 C10 5.1(2) . . . . ?
C25 C8 C9 C10 -177.66(13) . . . . ?
C8 C9 C10 C1 179.67(14) . . . . ?
C8 C9 C10 C4 3.0(2) . . . . ?
C2 C1 C10 C9 -174.24(13) . . . . ?
C11 C1 C10 C9 15.5(2) . . . . ?
C2 C1 C10 C4 2.96(14) . . . . ?
C11 C1 C10 C4 -167.30(12) . . . . ?
C5 C4 C10 C9 -8.4(2) . . . . ?
C3 C4 C10 C9 174.56(13) . . . . ?
C5 C4 C10 C1 174.44(13) . . . . ?
C3 C4 C10 C1 -2.62(14) . . . . ?
C12 O2 C11 O1 -5.93(19) . . . . ?
C12 O2 C11 C1 176.91(11) . . . . ?
C10 C1 C11 O1 -16.3(2) . . . . ?
C2 C1 C11 O1 175.41(14) . . . . ?
C10 C1 C11 O2 160.66(12) . . . . ?
C2 C1 C11 O2 -7.60(19) . . . . ?
C3 C2 C13 C14 134.06(14) . . . . ?
C1 C2 C13 C14 -42.6(2) . . . . ?
C3 C2 C13 C18 -41.84(19) . . . . ?
C1 C2 C13 C18 141.53(14) . . . . ?
C18 C13 C14 C15 -0.44(19) . . . . ?
C2 C13 C14 C15 -176.40(12) . . . . ?
C13 C14 C15 C16 -0.8(2) . . . . ?
C14 C15 C16 C17 0.94(19) . . . . ?
C14 C15 C16 C19 -179.20(12) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
C19 C16 C17 C18 -179.80(12) . . . . ?
C16 C17 C18 C13 -1.3(2) . . . . ?
C14 C13 C18 C17 1.4(2) . . . . ?
C2 C13 C18 C17 177.48(12) . . . . ?
C17 C16 C19 C24 24.67(19) . . . . ?
C15 C16 C19 C24 -155.19(13) . . . . ?
C17 C16 C19 C20 -155.31(13) . . . . ?
C15 C16 C19 C20 24.83(19) . . . . ?
C24 C19 C20 C21 0.2(2) . . . . ?
C16 C19 C20 C21 -179.81(12) . . . . ?
C19 C20 C21 C22 -0.4(2) . . . . ?
C20 C21 C22 C23 0.3(2) . . . . ?
C21 C22 C23 C24 -0.1(2) . . . . ?
C22 C23 C24 C19 -0.1(2) . . . . ?
C20 C19 C24 C23 0.0(2) . . . . ?
C16 C19 C24 C23 -179.99(13) . . . . ?
C9 C8 C25 C26 -109.46(15) . . . . ?
C7 C8 C25 C26 68.08(17) . . . . ?
C9 C8 C25 C27 126.29(14) . . . . ?
C7 C8 C25 C27 -56.17(17) . . . . ?
C37 C28 C29 C30 1.66(15) . . . . ?
C38 C28 C29 C30 -169.92(13) . . . . ?
C37 C28 C29 C40 -175.36(13) . . . . ?
C38 C28 C29 C40 13.1(2) . . . . ?
C28 C29 C30 C31 -0.57(16) . . . . ?
C40 C29 C30 C31 176.65(12) . . . . ?
C29 C30 C31 C32 177.20(13) . . . . ?
C29 C30 C31 C37 -0.70(15) . . . . ?
C30 C31 C32 C33 -179.04(14) . . . . ?
C37 C31 C32 C33 -1.6(2) . . . . ?
C31 C32 C33 C34 -2.2(3) . . . . ?
C32 C33 C34 C35 0.9(3) . . . . ?
C33 C34 C35 C36 3.1(3) . . . . ?
C33 C34 C35 C52 -176.71(15) . . . . ?
C34 C35 C36 C37 -3.1(2) . . . . ?
C52 C35 C36 C37 176.77(14) . . . . ?
C35 C36 C37 C28 179.09(14) . . . . ?
C35 C36 C37 C31 -1.6(2) . . . . ?
C29 C28 C37 C36 177.40(13) . . . . ?
C38 C28 C37 C36 -10.6(2) . . . . ?
C29 C28 C37 C31 -2.04(15) . . . . ?
C38 C28 C37 C31 169.98(12) . . . . ?
C32 C31 C37 C36 4.4(2) . . . . ?
C30 C31 C37 C36 -177.74(13) . . . . ?
C32 C31 C37 C28 -176.14(13) . . . . ?
C30 C31 C37 C28 1.69(15) . . . . ?
C39 O4 C38 O3 1.5(2) . . . . ?
C39 O4 C38 C28 -179.86(12) . . . . ?
C37 C28 C38 O3 23.9(2) . . . . ?
C29 C28 C38 O3 -165.68(15) . . . . ?
C37 C28 C38 O4 -154.68(13) . . . . ?
C29 C28 C38 O4 15.7(2) . . . . ?
C30 C29 C40 C45 40.26(19) . . . . ?
C28 C29 C40 C45 -143.11(14) . . . . ?
C30 C29 C40 C41 -138.08(14) . . . . ?
C28 C29 C40 C41 38.5(2) . . . . ?
C45 C40 C41 C42 1.0(2) . . . . ?
C29 C40 C41 C42 179.44(12) . . . . ?
C40 C41 C42 C43 -0.1(2) . . . . ?
C41 C42 C43 C44 -0.72(19) . . . . ?
C41 C42 C43 C46 179.47(12) . . . . ?
C42 C43 C44 C45 0.5(2) . . . . ?
C46 C43 C44 C45 -179.65(12) . . . . ?
C43 C44 C45 C40 0.4(2) . . . . ?
C41 C40 C45 C44 -1.2(2) . . . . ?
C29 C40 C45 C44 -179.63(12) . . . . ?
C44 C43 C46 C51 -18.5(2) . . . . ?
C42 C43 C46 C51 161.27(13) . . . . ?
C44 C43 C46 C47 161.97(13) . . . . ?
C42 C43 C46 C47 -18.2(2) . . . . ?
C51 C46 C47 C48 -1.4(2) . . . . ?
C43 C46 C47 C48 178.17(13) . . . . ?
C46 C47 C48 C49 1.4(2) . . . . ?
C47 C48 C49 C50 0.0(2) . . . . ?
C48 C49 C50 C51 -1.3(2) . . . . ?
C49 C50 C51 C46 1.3(2) . . . . ?
C47 C46 C51 C50 0.0(2) . . . . ?
C43 C46 C51 C50 -179.49(12) . . . . ?
C34 C35 C52 C54 -121.52(15) . . . . ?
C36 C35 C52 C54 58.64(17) . . . . ?
C34 C35 C52 C53 114.27(15) . . . . ?
C36 C35 C52 C53 -65.57(17) . . . . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_shelxl_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1883653'
loop_
_audit_author_name
_audit_author_address
'Shigeki Mori'
;Ehime Univeristy
Japan
;
_audit_update_record             
;
2018-12-07 deposited with the CCDC.	2019-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 N S'
_chemical_formula_sum            'C13 H9 N S'
_chemical_formula_weight         211.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   10.6375(5)
_cell_length_b                   16.3123(7)
_cell_length_c                   12.1927(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.832(5)
_cell_angle_gamma                90
_cell_volume                     2062.86(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13331
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      30.80

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.274
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.748
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku Varimax with Saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            34881
_diffrn_reflns_av_unetI/netI     0.0676
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.120
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4970
_reflns_number_gt                3610
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3.1 (Rigaku, 2018)'
_computing_publication_material  'CrystalStructure 4.3.1 (Rigaku, 2018)'
_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)+(0.0347P)²+1.6550P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4970
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.49959(6) 0.39968(4) 0.70075(6) 0.02592(17) Uani 1 1 d . . . . .
S2 S 0.53709(6) 0.74220(4) 0.52804(5) 0.01793(15) Uani 1 1 d . . . . .
N1 N 0.51245(19) 0.50239(12) 0.86217(17) 0.0201(4) Uani 1 1 d . . . . .
N2 N 0.71864(18) 0.75982(12) 0.42053(16) 0.0176(4) Uani 1 1 d . . . . .
C1 C 0.3917(2) 0.55635(14) 0.68254(19) 0.0153(5) Uani 1 1 d . . . . .
C2 C 0.3438(2) 0.55237(14) 0.56519(19) 0.0162(5) Uani 1 1 d . . . . .
H2 H 0.353918 0.507474 0.518284 0.019 Uiso 1 1 calc R U . . .
C3 C 0.2788(2) 0.62560(14) 0.52919(19) 0.0168(5) Uani 1 1 d . . . . .
C4 C 0.2177(2) 0.64523(15) 0.41890(19) 0.0194(5) Uani 1 1 d . . . . .
H4 H 0.217112 0.603347 0.364656 0.023 Uiso 1 1 calc R U . . .
C5 C 0.1575(2) 0.71824(16) 0.3781(2) 0.0253(6) Uani 1 1 d . . . . .
H5 H 0.122021 0.719641 0.299465 0.030 Uiso 1 1 calc R U . . .
C6 C 0.1420(2) 0.78935(16) 0.4362(2) 0.0242(6) Uani 1 1 d . . . . .
H6 H 0.100508 0.833102 0.390826 0.029 Uiso 1 1 calc R U . . .
C7 C 0.1780(2) 0.80641(15) 0.5507(2) 0.0222(5) Uani 1 1 d . . . . .
H7 H 0.156603 0.859654 0.572388 0.027 Uiso 1 1 calc R U . . .
C8 C 0.2406(2) 0.75634(14) 0.6372(2) 0.0189(5) Uani 1 1 d . . . . .
H8 H 0.253372 0.779127 0.710588 0.023 Uiso 1 1 calc R U . . .
C9 C 0.2875(2) 0.67728(14) 0.63173(19) 0.0156(5) Uani 1 1 d . . . . .
C10 C 0.3564(2) 0.63172(14) 0.72268(19) 0.0160(5) Uani 1 1 d . . . . .
H10 H 0.375987 0.648920 0.799025 0.019 Uiso 1 1 calc R U . . .
C11 C 0.4659(2) 0.49360(14) 0.7535(2) 0.0163(5) Uani 1 1 d . . . . .
C12 C 0.5810(2) 0.37164(15) 0.8323(2) 0.0241(6) Uani 1 1 d . . . . .
H12 H 0.622743 0.320384 0.850877 0.029 Uiso 1 1 calc R U . . .
C13 C 0.5777(2) 0.43275(15) 0.9061(2) 0.0232(6) Uani 1 1 d . . . . .
H13 H 0.617815 0.428012 0.983649 0.028 Uiso 1 1 calc R U . . .
C14 C 0.7690(2) 0.65929(13) 0.57543(18) 0.0141(5) Uani 1 1 d . . . . .
C15 C 0.7355(2) 0.61938(14) 0.66742(18) 0.0150(5) Uani 1 1 d . . . . .
H15 H 0.659366 0.628739 0.694147 0.018 Uiso 1 1 calc R U . . .
C16 C 0.8330(2) 0.56380(13) 0.71265(18) 0.0144(5) Uani 1 1 d . . . . .
C17 C 0.8350(2) 0.51487(14) 0.80621(19) 0.0178(5) Uani 1 1 d . . . . .
H17 H 0.763265 0.520595 0.840088 0.021 Uiso 1 1 calc R U . . .
C18 C 0.9277(2) 0.45888(15) 0.8567(2) 0.0214(5) Uani 1 1 d . . . . .
H18 H 0.911976 0.432009 0.921463 0.026 Uiso 1 1 calc R U . . .
C19 C 1.0417(2) 0.43664(15) 0.8247(2) 0.0233(6) Uani 1 1 d . . . . .
H19 H 1.092232 0.396358 0.870820 0.028 Uiso 1 1 calc R U . . .
C20 C 1.0917(2) 0.46466(15) 0.7359(2) 0.0238(6) Uani 1 1 d . . . . .
H20 H 1.170625 0.440071 0.729359 0.029 Uiso 1 1 calc R U . . .
C21 C 1.0434(2) 0.52332(14) 0.6551(2) 0.0185(5) Uani 1 1 d . . . . .
H21 H 1.093678 0.533368 0.601092 0.022 Uiso 1 1 calc R U . . .
C22 C 0.9312(2) 0.56927(13) 0.64274(19) 0.0150(5) Uani 1 1 d . . . . .
C23 C 0.8879(2) 0.62908(14) 0.56109(19) 0.0157(5) Uani 1 1 d . . . . .
H23 H 0.931693 0.646426 0.505175 0.019 Uiso 1 1 calc R U . . .
C24 C 0.6891(2) 0.72026(13) 0.50623(18) 0.0149(5) Uani 1 1 d . . . . .
C25 C 0.5116(2) 0.80688(14) 0.41597(19) 0.0208(5) Uani 1 1 d . . . . .
H25 H 0.434740 0.837229 0.389144 0.025 Uiso 1 1 calc R U . . .
C26 C 0.6163(2) 0.80894(15) 0.3705(2) 0.0225(5) Uani 1 1 d . . . . .
H26 H 0.619401 0.842457 0.307472 0.027 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C12 1.708(3) . ?
S1 C11 1.730(2) . ?
S2 C25 1.700(2) . ?
S2 C24 1.734(2) . ?
N1 C11 1.315(3) . ?
N1 C13 1.376(3) . ?
N2 C24 1.324(3) . ?
N2 C26 1.380(3) . ?
C1 C10 1.405(3) . ?
C1 C2 1.410(3) . ?
C1 C11 1.455(3) . ?
C2 C3 1.401(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(3) . ?
C3 C9 1.494(3) . ?
C4 C5 1.391(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.391(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.399(3) . ?
C10 H10 0.9500 . ?
C12 C13 1.349(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C23 1.405(3) . ?
C14 C15 1.409(3) . ?
C14 C24 1.451(3) . ?
C15 C16 1.396(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(3) . ?
C16 C22 1.490(3) . ?
C17 C18 1.384(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.401(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.389(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.397(3) . ?
C23 H23 0.9500 . ?
C25 C26 1.350(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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
C12 S1 C11 89.51(12) . . ?
C25 S2 C24 89.56(11) . . ?
C11 N1 C13 110.3(2) . . ?
C24 N2 C26 109.25(19) . . ?
C10 C1 C2 109.2(2) . . ?
C10 C1 C11 124.1(2) . . ?
C2 C1 C11 126.7(2) . . ?
C3 C2 C1 108.7(2) . . ?
C3 C2 H2 125.6 . . ?
C1 C2 H2 125.6 . . ?
C4 C3 C2 126.1(2) . . ?
C4 C3 C9 127.3(2) . . ?
C2 C3 C9 106.5(2) . . ?
C5 C4 C3 128.3(2) . . ?
C5 C4 H4 115.8 . . ?
C3 C4 H4 115.8 . . ?
C6 C5 C4 129.1(2) . . ?
C6 C5 H5 115.4 . . ?
C4 C5 H5 115.4 . . ?
C5 C6 C7 129.9(2) . . ?
C5 C6 H6 115.0 . . ?
C7 C6 H6 115.0 . . ?
C8 C7 C6 128.7(2) . . ?
C8 C7 H7 115.6 . . ?
C6 C7 H7 115.6 . . ?
C7 C8 C9 128.9(2) . . ?
C7 C8 H8 115.5 . . ?
C9 C8 H8 115.5 . . ?
C8 C9 C10 125.8(2) . . ?
C8 C9 C3 127.4(2) . . ?
C10 C9 C3 106.7(2) . . ?
C9 C10 C1 108.8(2) . . ?
C9 C10 H10 125.6 . . ?
C1 C10 H10 125.6 . . ?
N1 C11 C1 123.8(2) . . ?
N1 C11 S1 114.12(17) . . ?
C1 C11 S1 122.11(17) . . ?
C13 C12 S1 110.22(19) . . ?
C13 C12 H12 124.9 . . ?
S1 C12 H12 124.9 . . ?
C12 C13 N1 115.9(2) . . ?
C12 C13 H13 122.1 . . ?
N1 C13 H13 122.1 . . ?
C23 C14 C15 109.3(2) . . ?
C23 C14 C24 126.6(2) . . ?
C15 C14 C24 124.1(2) . . ?
C16 C15 C14 108.5(2) . . ?
C16 C15 H15 125.7 . . ?
C14 C15 H15 125.7 . . ?
C17 C16 C15 124.9(2) . . ?
C17 C16 C22 128.3(2) . . ?
C15 C16 C22 106.78(19) . . ?
C18 C17 C16 128.6(2) . . ?
C18 C17 H17 115.7 . . ?
C16 C17 H17 115.7 . . ?
C17 C18 C19 128.5(2) . . ?
C17 C18 H18 115.8 . . ?
C19 C18 H18 115.8 . . ?
C20 C19 C18 129.6(2) . . ?
C20 C19 H19 115.2 . . ?
C18 C19 H19 115.2 . . ?
C19 C20 C21 129.6(2) . . ?
C19 C20 H20 115.2 . . ?
C21 C20 H20 115.2 . . ?
C20 C21 C22 128.5(2) . . ?
C20 C21 H21 115.8 . . ?
C22 C21 H21 115.8 . . ?
C21 C22 C23 126.4(2) . . ?
C21 C22 C16 126.9(2) . . ?
C23 C22 C16 106.74(19) . . ?
C22 C23 C14 108.6(2) . . ?
C22 C23 H23 125.7 . . ?
C14 C23 H23 125.7 . . ?
N2 C24 C14 125.6(2) . . ?
N2 C24 S2 114.42(17) . . ?
C14 C24 S2 119.87(16) . . ?
C26 C25 S2 110.29(18) . . ?
C26 C25 H25 124.9 . . ?
S2 C25 H25 124.9 . . ?
C25 C26 N2 116.5(2) . . ?
C25 C26 H26 121.8 . . ?
N2 C26 H26 121.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 0.7(3) . . . . ?
C11 C1 C2 C3 -179.5(2) . . . . ?
C1 C2 C3 C4 -179.9(2) . . . . ?
C1 C2 C3 C9 -0.2(2) . . . . ?
C2 C3 C4 C5 -176.6(2) . . . . ?
C9 C3 C4 C5 3.8(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C7 -2.5(4) . . . . ?
C5 C6 C7 C8 0.8(4) . . . . ?
C6 C7 C8 C9 2.4(4) . . . . ?
C7 C8 C9 C10 176.3(2) . . . . ?
C7 C8 C9 C3 -1.5(4) . . . . ?
C4 C3 C9 C8 -2.5(4) . . . . ?
C2 C3 C9 C8 177.8(2) . . . . ?
C4 C3 C9 C10 179.3(2) . . . . ?
C2 C3 C9 C10 -0.4(2) . . . . ?
C8 C9 C10 C1 -177.4(2) . . . . ?
C3 C9 C10 C1 0.8(2) . . . . ?
C2 C1 C10 C9 -1.0(3) . . . . ?
C11 C1 C10 C9 179.2(2) . . . . ?
C13 N1 C11 C1 179.8(2) . . . . ?
C13 N1 C11 S1 0.2(2) . . . . ?
C10 C1 C11 N1 -3.1(3) . . . . ?
C2 C1 C11 N1 177.1(2) . . . . ?
C10 C1 C11 S1 176.55(18) . . . . ?
C2 C1 C11 S1 -3.2(3) . . . . ?
C12 S1 C11 N1 -0.25(19) . . . . ?
C12 S1 C11 C1 -179.93(19) . . . . ?
C11 S1 C12 C13 0.25(19) . . . . ?
S1 C12 C13 N1 -0.2(3) . . . . ?
C11 N1 C13 C12 0.0(3) . . . . ?
C23 C14 C15 C16 0.3(3) . . . . ?
C24 C14 C15 C16 178.8(2) . . . . ?
C14 C15 C16 C17 178.2(2) . . . . ?
C14 C15 C16 C22 -0.9(2) . . . . ?
C15 C16 C17 C18 -179.6(2) . . . . ?
C22 C16 C17 C18 -0.6(4) . . . . ?
C16 C17 C18 C19 -1.2(4) . . . . ?
C17 C18 C19 C20 0.4(5) . . . . ?
C18 C19 C20 C21 1.0(5) . . . . ?
C19 C20 C21 C22 -0.1(5) . . . . ?
C20 C21 C22 C23 178.5(2) . . . . ?
C20 C21 C22 C16 -2.3(4) . . . . ?
C17 C16 C22 C21 2.8(4) . . . . ?
C15 C16 C22 C21 -178.1(2) . . . . ?
C17 C16 C22 C23 -177.9(2) . . . . ?
C15 C16 C22 C23 1.2(2) . . . . ?
C21 C22 C23 C14 178.3(2) . . . . ?
C16 C22 C23 C14 -1.0(2) . . . . ?
C15 C14 C23 C22 0.5(3) . . . . ?
C24 C14 C23 C22 -178.0(2) . . . . ?
C26 N2 C24 C14 176.2(2) . . . . ?
C26 N2 C24 S2 -0.2(2) . . . . ?
C23 C14 C24 N2 -2.9(4) . . . . ?
C15 C14 C24 N2 178.8(2) . . . . ?
C23 C14 C24 S2 173.29(18) . . . . ?
C15 C14 C24 S2 -5.0(3) . . . . ?
C25 S2 C24 N2 0.52(19) . . . . ?
C25 S2 C24 C14 -176.11(19) . . . . ?
C24 S2 C25 C26 -0.64(19) . . . . ?
S2 C25 C26 N2 0.7(3) . . . . ?
C24 N2 C26 C25 -0.3(3) . . . . ?

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_shelxl_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1883652'
loop_
_audit_author_name
_audit_author_address
'Shigeki Mori'
;Ehime Univeristy
Japan
;
_audit_update_record             
;
2018-12-07 deposited with the CCDC.	2019-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N'
_chemical_formula_sum            'C15 H13 N'
_chemical_formula_weight         207.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.9324(5)
_cell_length_b                   5.7383(3)
_cell_length_c                   21.1175(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.605(6)
_cell_angle_gamma                90
_cell_volume                     1070.23(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6995
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      31.22

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku Varimax with Saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            17392
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.951
_diffrn_reflns_theta_max         27.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2582
_reflns_number_gt                1827
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3.1 (Rigaku, 2018)'
_computing_publication_material  'CrystalStructure 4.3.1 (Rigaku, 2018)'
_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)+(0.0624P)²+1.1639P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2582
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0694
_refine_ls_wR_factor_ref         0.1694
_refine_ls_wR_factor_gt          0.1528
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
N1 N 0.6121(2) 0.5125(4) 0.42702(9) 0.0267(5) Uani 1 1 d . . . . .
C1 C 0.2223(2) 0.8115(4) 0.26885(11) 0.0226(5) Uani 1 1 d . . . . .
H1 H 0.209949 0.951579 0.291451 0.027 Uiso 1 1 calc R U . . .
C2 C 0.3300(2) 0.6385(4) 0.28792(11) 0.0215(5) Uani 1 1 d . . . . .
C3 C 0.3163(2) 0.4607(4) 0.24138(11) 0.0233(5) Uani 1 1 d . . . . .
H3 H 0.377973 0.325459 0.242523 0.028 Uiso 1 1 calc R U . . .
C4 C 0.1966(2) 0.5170(4) 0.19322(10) 0.0225(5) Uani 1 1 d . . . . .
C5 C 0.1460(2) 0.3807(4) 0.14015(11) 0.0230(5) Uani 1 1 d . . . . .
H5 H 0.201086 0.241038 0.136330 0.028 Uiso 1 1 calc R U . . .
C6 C 0.0253(3) 0.4217(4) 0.09175(11) 0.0261(5) Uani 1 1 d . . . . .
H6 H 0.009311 0.306150 0.059232 0.031 Uiso 1 1 calc R U . . .
C7 C -0.0751(3) 0.6075(4) 0.08425(11) 0.0272(5) Uani 1 1 d . . . . .
H7 H -0.150021 0.601024 0.047265 0.033 Uiso 1 1 calc R U . . .
C8 C -0.0821(3) 0.8013(4) 0.12289(11) 0.0262(5) Uani 1 1 d . . . . .
H8 H -0.162381 0.906852 0.109171 0.031 Uiso 1 1 calc R U . . .
C9 C 0.0121(2) 0.8627(4) 0.17899(11) 0.0234(5) Uani 1 1 d . . . . .
H9 H -0.011713 1.005488 0.197979 0.028 Uiso 1 1 calc R U . . .
C10 C 0.1357(2) 0.7438(4) 0.21081(11) 0.0224(5) Uani 1 1 d . . . . .
C11 C 0.4355(2) 0.6360(4) 0.34761(10) 0.0220(5) Uani 1 1 d . . . . .
C12 C 0.5378(2) 0.4576(4) 0.36770(11) 0.0240(5) Uani 1 1 d . . . . .
H12 H 0.553049 0.320980 0.344064 0.029 Uiso 1 1 calc R U . . .
C13 C 0.5607(3) 0.7260(4) 0.44560(11) 0.0275(5) Uani 1 1 d . . . . .
H13 H 0.594734 0.803831 0.484817 0.033 Uiso 1 1 calc R U . . .
C14 C 0.4526(2) 0.8053(4) 0.39786(11) 0.0245(5) Uani 1 1 d . . . . .
H14 H 0.398333 0.947697 0.398010 0.029 Uiso 1 1 calc R U . . .
C15 C 0.7334(3) 0.3782(5) 0.46259(12) 0.0322(6) Uani 1 1 d . . . . .
H15A H 0.830905 0.448133 0.457422 0.039 Uiso 1 1 calc R U . . .
H15B H 0.729251 0.217883 0.446414 0.039 Uiso 1 1 calc R U . . .
H15C H 0.722193 0.377460 0.508048 0.039 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C12 1.364(3) . ?
N1 C13 1.386(3) . ?
N1 C15 1.445(3) . ?
C1 C2 1.398(3) . ?
C1 C10 1.403(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.409(3) . ?
C2 C11 1.457(3) . ?
C3 C4 1.399(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 C10 1.479(3) . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C11 C12 1.395(3) . ?
C11 C14 1.430(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.365(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C12 N1 C13 109.1(2) . . ?
C12 N1 C15 125.3(2) . . ?
C13 N1 C15 125.4(2) . . ?
C2 C1 C10 108.7(2) . . ?
C2 C1 H1 125.6 . . ?
C10 C1 H1 125.6 . . ?
C1 C2 C3 109.2(2) . . ?
C1 C2 C11 125.7(2) . . ?
C3 C2 C11 125.0(2) . . ?
C4 C3 C2 108.5(2) . . ?
C4 C3 H3 125.8 . . ?
C2 C3 H3 125.8 . . ?
C5 C4 C3 125.4(2) . . ?
C5 C4 C10 127.8(2) . . ?
C3 C4 C10 106.88(19) . . ?
C4 C5 C6 128.5(2) . . ?
C4 C5 H5 115.8 . . ?
C6 C5 H5 115.8 . . ?
C7 C6 C5 129.1(2) . . ?
C7 C6 H6 115.4 . . ?
C5 C6 H6 115.4 . . ?
C8 C7 C6 129.4(2) . . ?
C8 C7 H7 115.3 . . ?
C6 C7 H7 115.3 . . ?
C7 C8 C9 129.0(2) . . ?
C7 C8 H8 115.5 . . ?
C9 C8 H8 115.5 . . ?
C10 C9 C8 128.7(2) . . ?
C10 C9 H9 115.6 . . ?
C8 C9 H9 115.6 . . ?
C9 C10 C1 125.7(2) . . ?
C9 C10 C4 127.5(2) . . ?
C1 C10 C4 106.71(19) . . ?
C12 C11 C14 106.31(19) . . ?
C12 C11 C2 125.4(2) . . ?
C14 C11 C2 128.2(2) . . ?
N1 C12 C11 108.4(2) . . ?
N1 C12 H12 125.8 . . ?
C11 C12 H12 125.8 . . ?
C14 C13 N1 108.3(2) . . ?
C14 C13 H13 125.9 . . ?
N1 C13 H13 125.9 . . ?
C13 C14 C11 107.8(2) . . ?
C13 C14 H14 126.1 . . ?
C11 C14 H14 126.1 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C10 C1 C2 C3 1.6(2) . . . . ?
C10 C1 C2 C11 -175.97(19) . . . . ?
C1 C2 C3 C4 -1.7(2) . . . . ?
C11 C2 C3 C4 175.93(19) . . . . ?
C2 C3 C4 C5 -178.1(2) . . . . ?
C2 C3 C4 C10 1.1(2) . . . . ?
C3 C4 C5 C6 177.7(2) . . . . ?
C10 C4 C5 C6 -1.4(4) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 C9 1.4(4) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C8 C9 C10 C1 -177.2(2) . . . . ?
C8 C9 C10 C4 -1.3(4) . . . . ?
C2 C1 C10 C9 175.7(2) . . . . ?
C2 C1 C10 C4 -0.9(2) . . . . ?
C5 C4 C10 C9 2.5(4) . . . . ?
C3 C4 C10 C9 -176.6(2) . . . . ?
C5 C4 C10 C1 179.1(2) . . . . ?
C3 C4 C10 C1 -0.1(2) . . . . ?
C1 C2 C11 C12 176.8(2) . . . . ?
C3 C2 C11 C12 -0.4(3) . . . . ?
C1 C2 C11 C14 -0.6(3) . . . . ?
C3 C2 C11 C14 -177.8(2) . . . . ?
C13 N1 C12 C11 -0.6(2) . . . . ?
C15 N1 C12 C11 -176.2(2) . . . . ?
C14 C11 C12 N1 0.6(2) . . . . ?
C2 C11 C12 N1 -177.27(19) . . . . ?
C12 N1 C13 C14 0.4(2) . . . . ?
C15 N1 C13 C14 176.0(2) . . . . ?
N1 C13 C14 C11 0.0(2) . . . . ?
C12 C11 C14 C13 -0.4(2) . . . . ?
C2 C11 C14 C13 177.4(2) . . . . ?

_refine_diff_density_max         0.514
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_shelxl_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1883651'
loop_
_audit_author_name
_audit_author_address
'Shigeki Mori'
;Ehime Univeristy
Japan
;
_audit_update_record             
;
2018-12-07 deposited with the CCDC.	2019-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 O2'
_chemical_formula_sum            'C22 H22 O2'
_chemical_formula_weight         318.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   12.8804(4)
_cell_length_b                   9.8767(3)
_cell_length_c                   13.8827(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.424(3)
_cell_angle_gamma                90
_cell_volume                     1731.11(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13048
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      31.29

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku Varimax with Saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            14120
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.618
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4153
_reflns_number_gt                3954
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.986
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.996

_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 (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3.1 (Rigaku, 2018)'
_computing_publication_material  'CrystalStructure 4.3.1 (Rigaku, 2018)'
_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)+(0.0437P)²+0.4665P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 1814 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(5)
_chemical_absolute_configuration .
_refine_ls_number_reflns         4153
_refine_ls_number_parameters     221
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0826
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.35428(11) 0.36711(14) 0.50365(11) 0.0212(3) Uani 1 1 d . . . . .
O2 O 0.51276(10) 0.26706(13) 0.54902(10) 0.0172(3) Uani 1 1 d . . . . .
C1 C 0.51257(14) 0.49752(19) 0.51460(13) 0.0136(4) Uani 1 1 d . . . . .
C2 C 0.62162(14) 0.51858(19) 0.55780(13) 0.0136(3) Uani 1 1 d . . . . .
C3 C 0.65148(14) 0.64722(19) 0.53108(14) 0.0154(4) Uani 1 1 d . . . . .
H3 H 0.719971 0.685819 0.550654 0.019 Uiso 1 1 calc R U . . .
C4 C 0.56467(14) 0.71045(19) 0.47092(13) 0.0145(4) Uani 1 1 d . . . . .
C5 C 0.56605(15) 0.83818(19) 0.42991(14) 0.0167(4) Uani 1 1 d . . . . .
H5 H 0.630513 0.887004 0.448004 0.020 Uiso 1 1 calc R U . . .
C6 C 0.48543(16) 0.90405(19) 0.36580(14) 0.0190(4) Uani 1 1 d . . . . .
H6 H 0.502294 0.991940 0.345714 0.023 Uiso 1 1 calc R U . . .
C7 C 0.38258(15) 0.85879(19) 0.32662(14) 0.0170(4) Uani 1 1 d . . . . .
H7 H 0.340940 0.920391 0.282528 0.020 Uiso 1 1 calc R U . . .
C8 C 0.33118(15) 0.73898(18) 0.34136(14) 0.0143(3) Uani 1 1 d . . . . .
C9 C 0.37376(14) 0.63090(19) 0.40237(13) 0.0141(4) Uani 1 1 d . . . . .
H9 H 0.326482 0.557766 0.404961 0.017 Uiso 1 1 calc R U . . .
C10 C 0.47456(14) 0.61470(19) 0.45952(13) 0.0135(4) Uani 1 1 d . . . . .
C11 C 0.45030(14) 0.37495(18) 0.52114(13) 0.0139(3) Uani 1 1 d . . . . .
C12 C 0.45836(16) 0.1434(2) 0.56247(17) 0.0217(4) Uani 1 1 d . . . . .
H12A H 0.408295 0.121099 0.501710 0.026 Uiso 1 1 calc R U . . .
H12B H 0.419755 0.154916 0.616070 0.026 Uiso 1 1 calc R U . . .
H12C H 0.509969 0.069898 0.578806 0.026 Uiso 1 1 calc R U . . .
C13 C 0.69441(14) 0.42722(19) 0.62449(13) 0.0139(4) Uani 1 1 d . . . . .
C14 C 0.67380(14) 0.38969(19) 0.71658(14) 0.0155(4) Uani 1 1 d . . . . .
C15 C 0.74645(15) 0.3062(2) 0.77716(14) 0.0186(4) Uani 1 1 d . . . . .
H15 H 0.733676 0.280848 0.839795 0.022 Uiso 1 1 calc R U . . .
C16 C 0.83704(15) 0.2594(2) 0.74764(15) 0.0210(4) Uani 1 1 d . . . . .
H16 H 0.884819 0.201430 0.789461 0.025 Uiso 1 1 calc R U . . .
C17 C 0.85762(15) 0.2974(2) 0.65728(15) 0.0203(4) Uani 1 1 d . . . . .
H17 H 0.919617 0.266133 0.636924 0.024 Uiso 1 1 calc R U . . .
C18 C 0.78675(15) 0.38186(19) 0.59657(14) 0.0167(4) Uani 1 1 d . . . . .
H18 H 0.801436 0.409128 0.535021 0.020 Uiso 1 1 calc R U . . .
C19 C 0.57670(15) 0.4380(2) 0.75217(15) 0.0189(4) Uani 1 1 d . . . . .
H19A H 0.595296 0.456908 0.822797 0.023 Uiso 1 1 calc R U . . .
H19B H 0.521949 0.367774 0.739908 0.023 Uiso 1 1 calc R U . . .
H19C H 0.549858 0.520803 0.716905 0.023 Uiso 1 1 calc R U . . .
C20 C 0.21637(14) 0.7229(2) 0.28762(14) 0.0166(4) Uani 1 1 d . . . . .
H20 H 0.198799 0.802751 0.243077 0.020 Uiso 1 1 calc R U . . .
C21 C 0.19840(18) 0.5959(2) 0.22374(17) 0.0254(5) Uani 1 1 d . . . . .
H21A H 0.247554 0.595807 0.178139 0.031 Uiso 1 1 calc R U . . .
H21B H 0.125376 0.595129 0.186386 0.031 Uiso 1 1 calc R U . . .
H21C H 0.210729 0.515416 0.265689 0.031 Uiso 1 1 calc R U . . .
C22 C 0.14208(15) 0.7266(2) 0.36121(16) 0.0215(4) Uani 1 1 d . . . . .
H22A H 0.151861 0.811978 0.397844 0.026 Uiso 1 1 calc R U . . .
H22B H 0.158378 0.650556 0.407077 0.026 Uiso 1 1 calc R U . . .
H22C H 0.068493 0.719578 0.325788 0.026 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.215(2) . ?
O2 C11 1.345(2) . ?
O2 C12 1.439(2) . ?
C1 C10 1.420(3) . ?
C1 C2 1.429(2) . ?
C1 C11 1.465(2) . ?
C2 C3 1.399(3) . ?
C2 C13 1.485(2) . ?
C3 C4 1.403(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 C10 1.481(2) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.402(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.405(3) . ?
C8 C20 1.527(2) . ?
C9 C10 1.390(2) . ?
C9 H9 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.396(3) . ?
C13 C14 1.406(3) . ?
C14 C15 1.397(3) . ?
C14 C19 1.510(3) . ?
C15 C16 1.390(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.527(3) . ?
C20 C22 1.532(3) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C11 O2 C12 115.53(14) . . ?
C10 C1 C2 108.23(16) . . ?
C10 C1 C11 124.92(16) . . ?
C2 C1 C11 126.80(17) . . ?
C3 C2 C1 108.66(16) . . ?
C3 C2 C13 122.98(16) . . ?
C1 C2 C13 128.30(17) . . ?
C2 C3 C4 109.49(16) . . ?
C2 C3 H3 125.3 . . ?
C4 C3 H3 125.3 . . ?
C5 C4 C3 125.19(17) . . ?
C5 C4 C10 127.66(17) . . ?
C3 C4 C10 107.14(16) . . ?
C4 C5 C6 128.40(18) . . ?
C4 C5 H5 115.8 . . ?
C6 C5 H5 115.8 . . ?
C5 C6 C7 128.95(18) . . ?
C5 C6 H6 115.5 . . ?
C7 C6 H6 115.5 . . ?
C8 C7 C6 130.92(18) . . ?
C8 C7 H7 114.5 . . ?
C6 C7 H7 114.5 . . ?
C7 C8 C9 126.50(17) . . ?
C7 C8 C20 117.37(16) . . ?
C9 C8 C20 116.12(16) . . ?
C10 C9 C8 129.82(17) . . ?
C10 C9 H9 115.1 . . ?
C8 C9 H9 115.1 . . ?
C9 C10 C1 125.78(17) . . ?
C9 C10 C4 127.66(17) . . ?
C1 C10 C4 106.48(15) . . ?
O1 C11 O2 122.29(16) . . ?
O1 C11 C1 126.06(17) . . ?
O2 C11 C1 111.64(15) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 119.51(17) . . ?
C18 C13 C2 119.29(17) . . ?
C14 C13 C2 121.16(17) . . ?
C15 C14 C13 118.59(17) . . ?
C15 C14 C19 119.27(17) . . ?
C13 C14 C19 122.13(16) . . ?
C16 C15 C14 121.33(18) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C17 C16 C15 119.98(18) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.42(19) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C13 121.15(18) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C8 112.95(16) . . ?
C21 C20 C22 111.34(17) . . ?
C8 C20 C22 110.12(15) . . ?
C21 C20 H20 107.4 . . ?
C8 C20 H20 107.4 . . ?
C22 C20 H20 107.4 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C10 C1 C2 C3 0.5(2) . . . . ?
C11 C1 C2 C3 177.93(17) . . . . ?
C10 C1 C2 C13 177.61(18) . . . . ?
C11 C1 C2 C13 -4.9(3) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C13 C2 C3 C4 -177.66(17) . . . . ?
C2 C3 C4 C5 -179.14(18) . . . . ?
C2 C3 C4 C10 0.1(2) . . . . ?
C3 C4 C5 C6 176.21(19) . . . . ?
C10 C4 C5 C6 -2.9(3) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 1.5(4) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?
C6 C7 C8 C20 178.93(19) . . . . ?
C7 C8 C9 C10 -1.7(3) . . . . ?
C20 C8 C9 C10 179.40(18) . . . . ?
C8 C9 C10 C1 -175.94(19) . . . . ?
C8 C9 C10 C4 0.3(3) . . . . ?
C2 C1 C10 C9 176.43(17) . . . . ?
C11 C1 C10 C9 -1.1(3) . . . . ?
C2 C1 C10 C4 -0.43(19) . . . . ?
C11 C1 C10 C4 -177.93(17) . . . . ?
C5 C4 C10 C9 2.6(3) . . . . ?
C3 C4 C10 C9 -176.57(18) . . . . ?
C5 C4 C10 C1 179.42(18) . . . . ?
C3 C4 C10 C1 0.21(19) . . . . ?
C12 O2 C11 O1 -3.6(3) . . . . ?
C12 O2 C11 C1 176.84(16) . . . . ?
C10 C1 C11 O1 -20.4(3) . . . . ?
C2 C1 C11 O1 162.61(18) . . . . ?
C10 C1 C11 O2 159.21(17) . . . . ?
C2 C1 C11 O2 -17.8(3) . . . . ?
C3 C2 C13 C18 -62.1(2) . . . . ?
C1 C2 C13 C18 121.2(2) . . . . ?
C3 C2 C13 C14 115.6(2) . . . . ?
C1 C2 C13 C14 -61.1(3) . . . . ?
C18 C13 C14 C15 -0.8(3) . . . . ?
C2 C13 C14 C15 -178.44(17) . . . . ?
C18 C13 C14 C19 178.52(17) . . . . ?
C2 C13 C14 C19 0.8(3) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C19 C14 C15 C16 -179.86(18) . . . . ?
C14 C15 C16 C17 1.1(3) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C16 C17 C18 C13 -1.0(3) . . . . ?
C14 C13 C18 C17 1.6(3) . . . . ?
C2 C13 C18 C17 179.29(17) . . . . ?
C7 C8 C20 C21 123.9(2) . . . . ?
C9 C8 C20 C21 -57.1(2) . . . . ?
C7 C8 C20 C22 -110.95(19) . . . . ?
C9 C8 C20 C22 68.1(2) . . . . ?

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.042

