# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc1m6k6l
_database_code_depnum_ccdc_archive 'CCDC 1495849'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/chem.201700570 2017
_audit_update_record             
;
2016-07-25 deposited with the CCDC.	2020-04-24 downloaded from the CCDC.
;

_audit_creation_date             2016-05-25T09:40:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C31 H20'
_chemical_formula_moiety         'C31 H20'
_chemical_formula_weight         392.47

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.3029(16)
_cell_length_b                   9.8247(10)
_cell_length_c                   16.8935(19)
_cell_angle_alpha                90
_cell_angle_beta                 110.005(4)
_cell_angle_gamma                90
_cell_volume                     2074.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3842
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.27
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_T_max  0.998

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.6391  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#



#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_orient_matrix_ub_11      -0.040153
_diffrn_orient_matrix_ub_12      -0.051156
_diffrn_orient_matrix_ub_13      -0.052483
_diffrn_orient_matrix_ub_21      -0.064029
_diffrn_orient_matrix_ub_22      -0.003926
_diffrn_orient_matrix_ub_23      0.018165
_diffrn_orient_matrix_ub_31      -0.026226
_diffrn_orient_matrix_ub_32      0.087907
_diffrn_orient_matrix_ub_33      -0.02973
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.071
_diffrn_reflns_av_unetI/netI     0.059
_diffrn_reflns_number            20027
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.167
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_reflns_Friedel_coverage         0
_reflns_number_total             4750
_reflns_number_gt                3389
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²+0.7764P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4750
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.045

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.36895(11) 0.21762(15) 0.11780(9) 0.0168(3) Uani 1 1 d . . . . .
C2 C 0.29998(11) 0.20154(14) 0.17339(9) 0.0165(3) Uani 1 1 d . . . . .
C3 C 0.31487(12) 0.25926(15) 0.25104(9) 0.0195(3) Uani 1 1 d . . . . .
H3 H 0.3732 0.3191 0.2761 0.023 Uiso 1 1 calc R U . . .
C4 C 0.24300(12) 0.22832(15) 0.29205(9) 0.0199(3) Uani 1 1 d . . . . .
H4 H 0.2534 0.267 0.3458 0.024 Uiso 1 1 calc R U . . .
C5 C 0.15586(12) 0.14176(15) 0.25602(9) 0.0178(3) Uani 1 1 d . . . . .
C6 C 0.14206(12) 0.08281(15) 0.17774(9) 0.0190(3) Uani 1 1 d . . . . .
H6 H 0.0834 0.0236 0.1523 0.023 Uiso 1 1 calc R U . . .
C7 C 0.21494(12) 0.11133(15) 0.13710(9) 0.0173(3) Uani 1 1 d . . . . .
C8 C 0.22646(12) 0.05614(14) 0.05959(9) 0.0183(3) Uani 1 1 d . . . . .
C9 C 0.16415(13) -0.03650(16) 0.00092(10) 0.0239(4) Uani 1 1 d . . . . .
H9 H 0.0998 -0.0713 0.0056 0.029 Uiso 1 1 calc R U . . .
C10 C 0.19800(14) -0.07709(16) -0.06478(10) 0.0273(4) Uani 1 1 d . . . . .
H10 H 0.1561 -0.14 -0.1055 0.033 Uiso 1 1 calc R U . . .
C11 C 0.29245(14) -0.02671(16) -0.07168(10) 0.0266(4) Uani 1 1 d . . . . .
H11 H 0.3153 -0.0573 -0.1161 0.032 Uiso 1 1 calc R U . . .
C12 C 0.35364(13) 0.06815(15) -0.01405(10) 0.0221(3) Uani 1 1 d . . . . .
H12 H 0.4176 0.1034 -0.0192 0.026 Uiso 1 1 calc R U . . .
C13 C 0.31970(12) 0.11023(15) 0.05086(9) 0.0176(3) Uani 1 1 d . . . . .
C14 C 0.35976(12) 0.36068(14) 0.07954(9) 0.0166(3) Uani 1 1 d . . . . .
C15 C 0.26963(12) 0.42595(16) 0.02687(10) 0.0217(3) Uani 1 1 d . . . . .
H15 H 0.2021 0.3816 0.0088 0.026 Uiso 1 1 calc R U . . .
C16 C 0.27989(13) 0.55791(16) 0.00079(10) 0.0258(4) Uani 1 1 d . . . . .
H16 H 0.2187 0.6041 -0.0354 0.031 Uiso 1 1 calc R U . . .
C17 C 0.37897(14) 0.62313(17) 0.02721(10) 0.0264(4) Uani 1 1 d . . . . .
H17 H 0.3844 0.7137 0.0094 0.032 Uiso 1 1 calc R U . . .
C18 C 0.46966(13) 0.55715(16) 0.07924(10) 0.0226(3) Uani 1 1 d . . . . .
H18 H 0.5372 0.6014 0.097 0.027 Uiso 1 1 calc R U . . .
C19 C 0.45968(12) 0.42476(15) 0.10500(9) 0.0169(3) Uani 1 1 d . . . . .
C20 C 0.53965(12) 0.33158(15) 0.15961(9) 0.0174(3) Uani 1 1 d . . . . .
C21 C 0.64825(12) 0.34980(16) 0.20314(10) 0.0235(3) Uani 1 1 d . . . . .
H21 H 0.6831 0.4317 0.1974 0.028 Uiso 1 1 calc R U . . .
C22 C 0.70473(13) 0.24583(17) 0.25512(10) 0.0255(4) Uani 1 1 d . . . . .
H22 H 0.7789 0.2569 0.2855 0.031 Uiso 1 1 calc R U . . .
C23 C 0.65386(13) 0.12575(16) 0.26314(10) 0.0235(3) Uani 1 1 d . . . . .
H23 H 0.6936 0.056 0.2994 0.028 Uiso 1 1 calc R U . . .
C24 C 0.54545(12) 0.10617(15) 0.21878(9) 0.0205(3) Uani 1 1 d . . . . .
H24 H 0.5111 0.0236 0.224 0.025 Uiso 1 1 calc R U . . .
C25 C 0.48880(12) 0.20954(15) 0.16694(9) 0.0163(3) Uani 1 1 d . . . . .
C26 C 0.08131(12) 0.11418(16) 0.30286(9) 0.0192(3) Uani 1 1 d . . . . .
C27 C 0.05959(13) 0.21511(17) 0.35299(10) 0.0242(4) Uani 1 1 d . . . . .
H27 H 0.0911 0.3026 0.356 0.029 Uiso 1 1 calc R U . . .
C28 C -0.00754(14) 0.1889(2) 0.39848(11) 0.0319(4) Uani 1 1 d . . . . .
H28 H -0.0215 0.2585 0.4324 0.038 Uiso 1 1 calc R U . . .
C29 C -0.05413(14) 0.0627(2) 0.39494(11) 0.0356(4) Uani 1 1 d . . . . .
H29 H -0.1003 0.0454 0.426 0.043 Uiso 1 1 calc R U . . .
C30 C -0.03329(15) -0.0382(2) 0.34592(12) 0.0376(5) Uani 1 1 d . . . . .
H30 H -0.0653 -0.1253 0.3433 0.045 Uiso 1 1 calc R U . . .
C31 C 0.03426(14) -0.01319(18) 0.30037(11) 0.0292(4) Uani 1 1 d . . . . .
H31 H 0.0485 -0.0837 0.2672 0.035 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C13 1.521(2) . ?
C1 C25 1.527(2) . ?
C1 C2 1.5290(19) . ?
C1 C14 1.534(2) . ?
C2 C3 1.380(2) . ?
C2 C7 1.402(2) . ?
C3 C4 1.393(2) . ?
C3 H3 0.95 . ?
C4 C5 1.398(2) . ?
C4 H4 0.95 . ?
C5 C6 1.397(2) . ?
C5 C26 1.490(2) . ?
C6 C7 1.395(2) . ?
C6 H6 0.95 . ?
C7 C8 1.473(2) . ?
C8 C9 1.391(2) . ?
C8 C13 1.403(2) . ?
C9 C10 1.391(2) . ?
C9 H9 0.95 . ?
C10 C11 1.392(2) . ?
C10 H10 0.95 . ?
C11 C12 1.392(2) . ?
C11 H11 0.95 . ?
C12 C13 1.384(2) . ?
C12 H12 0.95 . ?
C14 C15 1.382(2) . ?
C14 C19 1.399(2) . ?
C15 C16 1.391(2) . ?
C15 H15 0.95 . ?
C16 C17 1.395(2) . ?
C16 H16 0.95 . ?
C17 C18 1.387(2) . ?
C17 H17 0.95 . ?
C18 C19 1.392(2) . ?
C18 H18 0.95 . ?
C19 C20 1.466(2) . ?
C20 C21 1.390(2) . ?
C20 C25 1.403(2) . ?
C21 C22 1.388(2) . ?
C21 H21 0.95 . ?
C22 C23 1.390(2) . ?
C22 H22 0.95 . ?
C23 C24 1.393(2) . ?
C23 H23 0.95 . ?
C24 C25 1.384(2) . ?
C24 H24 0.95 . ?
C26 C31 1.393(2) . ?
C26 C27 1.397(2) . ?
C27 C28 1.387(2) . ?
C27 H27 0.95 . ?
C28 C29 1.378(3) . ?
C28 H28 0.95 . ?
C29 C30 1.380(3) . ?
C29 H29 0.95 . ?
C30 C31 1.390(2) . ?
C30 H30 0.95 . ?
C31 H31 0.95 . ?

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
C13 C1 C25 118.17(12) . . ?
C13 C1 C2 100.87(11) . . ?
C25 C1 C2 113.26(12) . . ?
C13 C1 C14 111.73(12) . . ?
C25 C1 C14 101.21(11) . . ?
C2 C1 C14 112.04(11) . . ?
C3 C2 C7 120.48(13) . . ?
C3 C2 C1 128.34(14) . . ?
C7 C2 C1 111.14(12) . . ?
C2 C3 C4 118.92(14) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 121.61(14) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 119.02(13) . . ?
C6 C5 C26 122.11(14) . . ?
C4 C5 C26 118.87(13) . . ?
C7 C6 C5 119.62(14) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C2 120.29(13) . . ?
C6 C7 C8 131.68(14) . . ?
C2 C7 C8 107.91(12) . . ?
C9 C8 C13 120.37(14) . . ?
C9 C8 C7 131.02(14) . . ?
C13 C8 C7 108.59(13) . . ?
C10 C9 C8 118.64(15) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C9 C10 C11 120.84(15) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 120.54(15) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 118.88(15) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C8 120.66(14) . . ?
C12 C13 C1 128.45(14) . . ?
C8 C13 C1 110.85(12) . . ?
C15 C14 C19 120.85(14) . . ?
C15 C14 C1 128.52(13) . . ?
C19 C14 C1 110.63(12) . . ?
C14 C15 C16 118.61(15) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C15 C16 C17 120.75(15) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 120.68(15) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 118.65(15) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C18 C19 C14 120.44(14) . . ?
C18 C19 C20 130.82(14) . . ?
C14 C19 C20 108.73(12) . . ?
C21 C20 C25 120.56(14) . . ?
C21 C20 C19 130.65(14) . . ?
C25 C20 C19 108.74(13) . . ?
C22 C21 C20 118.65(14) . . ?
C22 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C21 C22 C23 120.67(15) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 120.94(15) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C25 C24 C23 118.60(14) . . ?
C25 C24 H24 120.7 . . ?
C23 C24 H24 120.7 . . ?
C24 C25 C20 120.57(14) . . ?
C24 C25 C1 128.57(13) . . ?
C20 C25 C1 110.67(12) . . ?
C31 C26 C27 118.16(14) . . ?
C31 C26 C5 121.40(14) . . ?
C27 C26 C5 120.41(14) . . ?
C28 C27 C26 120.67(16) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C29 C28 C27 120.53(17) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 119.53(16) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C29 C30 C31 120.39(17) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C30 C31 C26 120.71(16) . . ?
C30 C31 H31 119.6 . . ?
C26 C31 H31 119.6 . . ?

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
C13 C1 C2 C3 170.63(15) . . . . ?
C25 C1 C2 C3 43.3(2) . . . . ?
C14 C1 C2 C3 -70.39(19) . . . . ?
C13 C1 C2 C7 -7.01(15) . . . . ?
C25 C1 C2 C7 -134.30(13) . . . . ?
C14 C1 C2 C7 111.96(14) . . . . ?
C7 C2 C3 C4 -1.1(2) . . . . ?
C1 C2 C3 C4 -178.56(14) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
C3 C4 C5 C26 -179.30(14) . . . . ?
C4 C5 C6 C7 -0.1(2) . . . . ?
C26 C5 C6 C7 -179.41(14) . . . . ?
C5 C6 C7 C2 -1.7(2) . . . . ?
C5 C6 C7 C8 173.82(15) . . . . ?
C3 C2 C7 C6 2.4(2) . . . . ?
C1 C2 C7 C6 -179.77(13) . . . . ?
C3 C2 C7 C8 -174.15(13) . . . . ?
C1 C2 C7 C8 3.71(16) . . . . ?
C6 C7 C8 C9 3.9(3) . . . . ?
C2 C7 C8 C9 179.88(15) . . . . ?
C6 C7 C8 C13 -174.34(15) . . . . ?
C2 C7 C8 C13 1.63(17) . . . . ?
C13 C8 C9 C10 1.9(2) . . . . ?
C7 C8 C9 C10 -176.17(15) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C9 C10 C11 C12 -1.6(2) . . . . ?
C10 C11 C12 C13 0.8(2) . . . . ?
C11 C12 C13 C8 1.4(2) . . . . ?
C11 C12 C13 C1 -176.16(14) . . . . ?
C9 C8 C13 C12 -2.8(2) . . . . ?
C7 C8 C13 C12 175.70(13) . . . . ?
C9 C8 C13 C1 175.17(13) . . . . ?
C7 C8 C13 C1 -6.37(17) . . . . ?
C25 C1 C13 C12 -50.3(2) . . . . ?
C2 C1 C13 C12 -174.26(15) . . . . ?
C14 C1 C13 C12 66.54(19) . . . . ?
C25 C1 C13 C8 132.01(13) . . . . ?
C2 C1 C13 C8 8.02(15) . . . . ?
C14 C1 C13 C8 -111.19(14) . . . . ?
C13 C1 C14 C15 52.20(19) . . . . ?
C25 C1 C14 C15 178.87(14) . . . . ?
C2 C1 C14 C15 -60.15(19) . . . . ?
C13 C1 C14 C19 -127.77(13) . . . . ?
C25 C1 C14 C19 -1.11(15) . . . . ?
C2 C1 C14 C19 119.87(13) . . . . ?
C19 C14 C15 C16 -1.1(2) . . . . ?
C1 C14 C15 C16 178.89(14) . . . . ?
C14 C15 C16 C17 0.0(2) . . . . ?
C15 C16 C17 C18 0.8(2) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C17 C18 C19 C14 -0.8(2) . . . . ?
C17 C18 C19 C20 -179.34(15) . . . . ?
C15 C14 C19 C18 1.5(2) . . . . ?
C1 C14 C19 C18 -178.48(13) . . . . ?
C15 C14 C19 C20 -179.59(13) . . . . ?
C1 C14 C19 C20 0.39(16) . . . . ?
C18 C19 C20 C21 1.8(3) . . . . ?
C14 C19 C20 C21 -176.92(15) . . . . ?
C18 C19 C20 C25 179.30(15) . . . . ?
C14 C19 C20 C25 0.59(16) . . . . ?
C25 C20 C21 C22 -1.2(2) . . . . ?
C19 C20 C21 C22 176.10(15) . . . . ?
C20 C21 C22 C23 0.3(2) . . . . ?
C21 C22 C23 C24 0.6(2) . . . . ?
C22 C23 C24 C25 -0.6(2) . . . . ?
C23 C24 C25 C20 -0.2(2) . . . . ?
C23 C24 C25 C1 -174.63(14) . . . . ?
C21 C20 C25 C24 1.1(2) . . . . ?
C19 C20 C25 C24 -176.66(13) . . . . ?
C21 C20 C25 C1 176.46(13) . . . . ?
C19 C20 C25 C1 -1.34(16) . . . . ?
C13 C1 C25 C24 -61.4(2) . . . . ?
C2 C1 C25 C24 56.21(19) . . . . ?
C14 C1 C25 C24 176.33(14) . . . . ?
C13 C1 C25 C20 123.77(14) . . . . ?
C2 C1 C25 C20 -118.64(13) . . . . ?
C14 C1 C25 C20 1.48(14) . . . . ?
C6 C5 C26 C31 35.3(2) . . . . ?
C4 C5 C26 C31 -144.02(16) . . . . ?
C6 C5 C26 C27 -146.85(15) . . . . ?
C4 C5 C26 C27 33.8(2) . . . . ?
C31 C26 C27 C28 -0.4(2) . . . . ?
C5 C26 C27 C28 -178.30(15) . . . . ?
C26 C27 C28 C29 -0.1(3) . . . . ?
C27 C28 C29 C30 0.2(3) . . . . ?
C28 C29 C30 C31 0.0(3) . . . . ?
C29 C30 C31 C26 -0.5(3) . . . . ?
C27 C26 C31 C30 0.7(2) . . . . ?
C5 C26 C31 C30 178.57(16) . . . . ?



# END of CIF
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1987304'
loop_
_audit_author_name
_audit_author_address
jeannin
;university of rennes
France
;
_audit_update_record             
;
2020-02-29 deposited with the CCDC.	2020-04-24 downloaded from the CCDC.
;

_audit_creation_date             2018-11-15T14:59:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C37 H24'
_chemical_formula_moiety         'C37 H24'
_chemical_formula_weight         468.56

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/a
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   16.6398(11)
_cell_length_b                   9.5620(6)
_cell_length_c                   16.8786(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.273(4)
_cell_angle_gamma                90
_cell_volume                     2578.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1807
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      20.31
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.999

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.6731  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      0.006199
_diffrn_orient_matrix_ub_12      0.010243
_diffrn_orient_matrix_ub_13      0.060382
_diffrn_orient_matrix_ub_21      -0.044135
_diffrn_orient_matrix_ub_22      0.074172
_diffrn_orient_matrix_ub_23      -0.012171
_diffrn_orient_matrix_ub_31      -0.043967
_diffrn_orient_matrix_ub_32      -0.073012
_diffrn_orient_matrix_ub_33      -0.003894
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_av_unetI/netI     0.1343
_diffrn_reflns_number            17443
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.473
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_reflns_Friedel_coverage         0
_reflns_number_total             5857
_reflns_number_gt                2428
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0565P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5857
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1906
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1533
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_restrained_S_all      0.967
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.81580(15) 0.1900(2) 0.76325(15) 0.0438(6) Uani 1 1 d . . . . .
C2 C 0.75695(15) 0.0769(2) 0.71451(15) 0.0410(6) Uani 1 1 d . . . . .
C3 C 0.75169(16) 0.0236(3) 0.63735(16) 0.0488(7) Uani 1 1 d . . . . .
H3 H 0.789218 0.051911 0.608767 0.059 Uiso 1 1 calc R U . . .
C4 C 0.68959(16) -0.0729(3) 0.60309(16) 0.0477(7) Uani 1 1 d . . . . .
H4 H 0.685453 -0.10794 0.550703 0.057 Uiso 1 1 calc R U . . .
C5 C 0.63299(15) -0.1191(2) 0.64486(15) 0.0376(6) Uani 1 1 d . . . . .
C6 C 0.64025(15) -0.0654(2) 0.72352(14) 0.0376(6) Uani 1 1 d . . . . .
H6 H 0.60363 -0.095071 0.752805 0.045 Uiso 1 1 calc R U . . .
C7 C 0.70176(15) 0.0318(2) 0.75804(14) 0.0349(6) Uani 1 1 d . . . . .
C8 C 0.71876(14) 0.1109(2) 0.83568(14) 0.0344(6) Uani 1 1 d . . . . .
C9 C 0.68009(15) 0.1057(2) 0.89834(14) 0.0390(6) Uani 1 1 d . . . . .
H9 H 0.637087 0.042094 0.895499 0.047 Uiso 1 1 calc R U . . .
C10 C 0.70552(15) 0.1955(2) 0.96551(15) 0.0415(6) Uani 1 1 d . . . . .
C11 C 0.77009(17) 0.2904(3) 0.96754(16) 0.0516(7) Uani 1 1 d . . . . .
H11 H 0.787434 0.351113 1.012135 0.062 Uiso 1 1 calc R U . . .
C12 C 0.80904(16) 0.2964(3) 0.90466(16) 0.0502(7) Uani 1 1 d . . . . .
H12 H 0.851809 0.360324 0.907131 0.06 Uiso 1 1 calc R U . . .
C13 C 0.78325(15) 0.2061(2) 0.83843(15) 0.0400(6) Uani 1 1 d . . . . .
C14 C 0.56361(15) -0.2156(2) 0.60564(15) 0.0394(6) Uani 1 1 d . . . . .
C15 C 0.52003(18) -0.2026(3) 0.52304(16) 0.0586(8) Uani 1 1 d . . . . .
H15 H 0.536826 -0.13584 0.490919 0.07 Uiso 1 1 calc R U . . .
C16 C 0.45198(19) -0.2871(3) 0.48737(18) 0.0728(9) Uani 1 1 d . . . . .
H16 H 0.423321 -0.276454 0.431872 0.087 Uiso 1 1 calc R U . . .
C17 C 0.4269(2) -0.3865(3) 0.5338(2) 0.0716(9) Uani 1 1 d . . . . .
H17 H 0.381169 -0.443429 0.510102 0.086 Uiso 1 1 calc R U . . .
C18 C 0.46928(19) -0.4012(3) 0.61495(19) 0.0671(9) Uani 1 1 d . . . . .
H18 H 0.452453 -0.468993 0.646441 0.081 Uiso 1 1 calc R U . . .
C19 C 0.53661(17) -0.3172(3) 0.65101(16) 0.0544(8) Uani 1 1 d . . . . .
H19 H 0.564504 -0.328714 0.706646 0.065 Uiso 1 1 calc R U . . .
C20 C 0.66385(17) 0.1911(2) 1.03272(15) 0.0443(7) Uani 1 1 d . . . . .
C21 C 0.57846(19) 0.1707(3) 1.01556(17) 0.0565(8) Uani 1 1 d . . . . .
H21 H 0.54622 0.162943 0.96098 0.068 Uiso 1 1 calc R U . . .
C22 C 0.5402(2) 0.1617(3) 1.0784(2) 0.0730(9) Uani 1 1 d . . . . .
H22 H 0.482797 0.146723 1.065908 0.088 Uiso 1 1 calc R U . . .
C23 C 0.5871(3) 0.1749(3) 1.1595(2) 0.0768(10) Uani 1 1 d . . . . .
H23 H 0.561576 0.167743 1.201756 0.092 Uiso 1 1 calc R U . . .
C24 C 0.6713(3) 0.1986(3) 1.17742(18) 0.0743(10) Uani 1 1 d . . . . .
H24 H 0.702814 0.210222 1.231986 0.089 Uiso 1 1 calc R U . . .
C25 C 0.7097(2) 0.2054(3) 1.11509(17) 0.0616(8) Uani 1 1 d . . . . .
H25 H 0.767176 0.219746 1.128216 0.074 Uiso 1 1 calc R U . . .
C26 C 0.90783(16) 0.1459(3) 0.78567(17) 0.0475(7) Uani 1 1 d . . . . .
C27 C 0.94692(18) 0.0394(3) 0.83643(18) 0.0595(8) Uani 1 1 d . . . . .
H27 H 0.916971 -0.017168 0.862867 0.071 Uiso 1 1 calc R U . . .
C28 C 1.0322(2) 0.0173(3) 0.8478(2) 0.0713(9) Uani 1 1 d . . . . .
H28 H 1.059673 -0.054327 0.88215 0.086 Uiso 1 1 calc R U . . .
C29 C 1.07611(19) 0.1021(4) 0.8079(2) 0.0715(9) Uani 1 1 d . . . . .
H29 H 1.132903 0.086278 0.815448 0.086 Uiso 1 1 calc R U . . .
C30 C 1.03698(19) 0.2093(3) 0.75743(18) 0.0642(8) Uani 1 1 d . . . . .
H30 H 1.066964 0.264875 0.730528 0.077 Uiso 1 1 calc R U . . .
C31 C 0.95224(17) 0.2339(3) 0.74683(16) 0.0484(7) Uani 1 1 d . . . . .
C32 C 0.89608(17) 0.3416(3) 0.70116(16) 0.0486(7) Uani 1 1 d . . . . .
C33 C 0.9097(2) 0.4544(3) 0.65393(17) 0.0615(8) Uani 1 1 d . . . . .
H33 H 0.962301 0.469365 0.646386 0.074 Uiso 1 1 calc R U . . .
C34 C 0.8443(3) 0.5429(3) 0.61873(17) 0.0679(9) Uani 1 1 d . . . . .
H34 H 0.852992 0.618189 0.587257 0.081 Uiso 1 1 calc R U . . .
C35 C 0.7660(2) 0.5216(3) 0.62942(16) 0.0641(9) Uani 1 1 d . . . . .
H35 H 0.722581 0.582631 0.605143 0.077 Uiso 1 1 calc R U . . .
C36 C 0.75144(19) 0.4098(3) 0.67613(16) 0.0550(7) Uani 1 1 d . . . . .
H36 H 0.698666 0.395231 0.683315 0.066 Uiso 1 1 calc R U . . .
C37 C 0.81692(18) 0.3208(3) 0.71165(16) 0.0466(7) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C13 1.521(3) . ?
C1 C37 1.527(3) . ?
C1 C26 1.530(3) . ?
C1 C2 1.534(3) . ?
C2 C3 1.378(3) . ?
C2 C7 1.396(3) . ?
C3 C4 1.385(3) . ?
C3 H3 0.93 . ?
C4 C5 1.397(3) . ?
C4 H4 0.93 . ?
C5 C6 1.397(3) . ?
C5 C14 1.481(3) . ?
C6 C7 1.385(3) . ?
C6 H6 0.93 . ?
C7 C8 1.470(3) . ?
C8 C9 1.384(3) . ?
C8 C13 1.398(3) . ?
C9 C10 1.390(3) . ?
C9 H9 0.93 . ?
C10 C11 1.400(3) . ?
C10 C20 1.487(3) . ?
C11 C12 1.391(3) . ?
C11 H11 0.93 . ?
C12 C13 1.383(3) . ?
C12 H12 0.93 . ?
C14 C15 1.385(3) . ?
C14 C19 1.388(3) . ?
C15 C16 1.384(4) . ?
C15 H15 0.93 . ?
C16 C17 1.369(4) . ?
C16 H16 0.93 . ?
C17 C18 1.361(4) . ?
C17 H17 0.93 . ?
C18 C19 1.374(4) . ?
C18 H18 0.93 . ?
C19 H19 0.93 . ?
C20 C21 1.382(3) . ?
C20 C25 1.392(3) . ?
C21 C22 1.384(3) . ?
C21 H21 0.93 . ?
C22 C23 1.378(4) . ?
C22 H22 0.93 . ?
C23 C24 1.367(4) . ?
C23 H23 0.93 . ?
C24 C25 1.377(4) . ?
C24 H24 0.93 . ?
C25 H25 0.93 . ?
C26 C27 1.372(4) . ?
C26 C31 1.399(3) . ?
C27 C28 1.394(4) . ?
C27 H27 0.93 . ?
C28 C29 1.385(4) . ?
C28 H28 0.93 . ?
C29 C30 1.375(4) . ?
C29 H29 0.93 . ?
C30 C31 1.391(4) . ?
C30 H30 0.93 . ?
C31 C32 1.457(4) . ?
C32 C37 1.392(3) . ?
C32 C33 1.396(4) . ?
C33 C34 1.375(4) . ?
C33 H33 0.93 . ?
C34 C35 1.380(4) . ?
C34 H34 0.93 . ?
C35 C36 1.389(4) . ?
C35 H35 0.93 . ?
C36 C37 1.380(4) . ?
C36 H36 0.93 . ?

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
C13 C1 C37 117.2(2) . . ?
C13 C1 C26 112.8(2) . . ?
C37 C1 C26 101.3(2) . . ?
C13 C1 C2 101.29(19) . . ?
C37 C1 C2 112.3(2) . . ?
C26 C1 C2 112.5(2) . . ?
C3 C2 C7 120.4(2) . . ?
C3 C2 C1 129.0(2) . . ?
C7 C2 C1 110.5(2) . . ?
C2 C3 C4 118.9(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 122.0(2) . . ?
C3 C4 H4 119 . . ?
C5 C4 H4 119 . . ?
C6 C5 C4 118.2(2) . . ?
C6 C5 C14 120.2(2) . . ?
C4 C5 C14 121.5(2) . . ?
C7 C6 C5 120.2(2) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 120.3(2) . . ?
C6 C7 C8 131.0(2) . . ?
C2 C7 C8 108.6(2) . . ?
C9 C8 C13 121.0(2) . . ?
C9 C8 C7 130.4(2) . . ?
C13 C8 C7 108.6(2) . . ?
C8 C9 C10 120.0(2) . . ?
C8 C9 H9 120 . . ?
C10 C9 H9 120 . . ?
C9 C10 C11 118.5(2) . . ?
C9 C10 C20 120.3(2) . . ?
C11 C10 C20 121.3(2) . . ?
C12 C11 C10 121.8(2) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C13 C12 C11 119.1(2) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C8 119.7(2) . . ?
C12 C13 C1 129.5(2) . . ?
C8 C13 C1 110.9(2) . . ?
C15 C14 C19 117.3(2) . . ?
C15 C14 C5 121.1(2) . . ?
C19 C14 C5 121.5(2) . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 120.0(3) . . ?
C17 C16 H16 120 . . ?
C15 C16 H16 120 . . ?
C18 C17 C16 119.5(3) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.9(3) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C14 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C21 C20 C25 117.8(3) . . ?
C21 C20 C10 121.1(2) . . ?
C25 C20 C10 121.1(3) . . ?
C20 C21 C22 121.0(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 120.1(3) . . ?
C23 C22 H22 120 . . ?
C21 C22 H22 120 . . ?
C24 C23 C22 119.7(3) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.3(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C20 121.1(3) . . ?
C24 C25 H25 119.4 . . ?
C20 C25 H25 119.4 . . ?
C27 C26 C31 121.3(3) . . ?
C27 C26 C1 128.7(2) . . ?
C31 C26 C1 110.0(2) . . ?
C26 C27 C28 119.0(3) . . ?
C26 C27 H27 120.5 . . ?
C28 C27 H27 120.5 . . ?
C29 C28 C27 119.9(3) . . ?
C29 C28 H28 120 . . ?
C27 C28 H28 120 . . ?
C30 C29 C28 121.0(3) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C29 C30 C31 119.6(3) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C30 C31 C26 119.2(3) . . ?
C30 C31 C32 131.7(3) . . ?
C26 C31 C32 109.2(2) . . ?
C37 C32 C33 119.6(3) . . ?
C37 C32 C31 108.7(2) . . ?
C33 C32 C31 131.6(3) . . ?
C34 C33 C32 119.1(3) . . ?
C34 C33 H33 120.5 . . ?
C32 C33 H33 120.5 . . ?
C33 C34 C35 121.0(3) . . ?
C33 C34 H34 119.5 . . ?
C35 C34 H34 119.5 . . ?
C34 C35 C36 120.6(3) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C37 C36 C35 118.6(3) . . ?
C37 C36 H36 120.7 . . ?
C35 C36 H36 120.7 . . ?
C36 C37 C32 121.1(2) . . ?
C36 C37 C1 128.2(2) . . ?
C32 C37 C1 110.7(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
C13 C1 C2 C3 175.3(2) . . . . ?
C37 C1 C2 C3 49.5(3) . . . . ?
C26 C1 C2 C3 -64.0(3) . . . . ?
C13 C1 C2 C7 -2.3(3) . . . . ?
C37 C1 C2 C7 -128.2(2) . . . . ?
C26 C1 C2 C7 118.4(2) . . . . ?
C7 C2 C3 C4 1.5(4) . . . . ?
C1 C2 C3 C4 -176.0(2) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C3 C4 C5 C14 176.2(2) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C14 C5 C6 C7 -175.8(2) . . . . ?
C5 C6 C7 C2 0.0(3) . . . . ?
C5 C6 C7 C8 175.0(2) . . . . ?
C3 C2 C7 C6 -1.1(3) . . . . ?
C1 C2 C7 C6 176.8(2) . . . . ?
C3 C2 C7 C8 -177.0(2) . . . . ?
C1 C2 C7 C8 0.9(3) . . . . ?
C6 C7 C8 C9 3.4(4) . . . . ?
C2 C7 C8 C9 178.8(2) . . . . ?
C6 C7 C8 C13 -174.3(2) . . . . ?
C2 C7 C8 C13 1.2(3) . . . . ?
C13 C8 C9 C10 -0.3(3) . . . . ?
C7 C8 C9 C10 -177.7(2) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C8 C9 C10 C20 179.6(2) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C20 C10 C11 C12 -179.4(2) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C8 0.1(3) . . . . ?
C11 C12 C13 C1 -179.0(2) . . . . ?
C9 C8 C13 C12 0.1(3) . . . . ?
C7 C8 C13 C12 177.9(2) . . . . ?
C9 C8 C13 C1 179.4(2) . . . . ?
C7 C8 C13 C1 -2.7(3) . . . . ?
C37 C1 C13 C12 -55.2(4) . . . . ?
C26 C1 C13 C12 61.8(3) . . . . ?
C2 C1 C13 C12 -177.7(2) . . . . ?
C37 C1 C13 C8 125.6(2) . . . . ?
C26 C1 C13 C8 -117.4(2) . . . . ?
C2 C1 C13 C8 3.1(3) . . . . ?
C6 C5 C14 C15 137.5(3) . . . . ?
C4 C5 C14 C15 -38.7(3) . . . . ?
C6 C5 C14 C19 -38.8(3) . . . . ?
C4 C5 C14 C19 145.0(2) . . . . ?
C19 C14 C15 C16 0.4(4) . . . . ?
C5 C14 C15 C16 -176.1(2) . . . . ?
C14 C15 C16 C17 -0.4(5) . . . . ?
C15 C16 C17 C18 0.0(5) . . . . ?
C16 C17 C18 C19 0.4(5) . . . . ?
C17 C18 C19 C14 -0.4(4) . . . . ?
C15 C14 C19 C18 0.0(4) . . . . ?
C5 C14 C19 C18 176.4(2) . . . . ?
C9 C10 C20 C21 -38.6(3) . . . . ?
C11 C10 C20 C21 140.6(3) . . . . ?
C9 C10 C20 C25 140.5(2) . . . . ?
C11 C10 C20 C25 -40.3(3) . . . . ?
C25 C20 C21 C22 -1.4(4) . . . . ?
C10 C20 C21 C22 177.7(2) . . . . ?
C20 C21 C22 C23 0.9(4) . . . . ?
C21 C22 C23 C24 0.8(5) . . . . ?
C22 C23 C24 C25 -1.8(5) . . . . ?
C23 C24 C25 C20 1.2(4) . . . . ?
C21 C20 C25 C24 0.4(4) . . . . ?
C10 C20 C25 C24 -178.8(2) . . . . ?
C13 C1 C26 C27 49.1(3) . . . . ?
C37 C1 C26 C27 175.2(2) . . . . ?
C2 C1 C26 C27 -64.7(3) . . . . ?
C13 C1 C26 C31 -129.9(2) . . . . ?
C37 C1 C26 C31 -3.9(3) . . . . ?
C2 C1 C26 C31 116.2(2) . . . . ?
C31 C26 C27 C28 -1.4(4) . . . . ?
C1 C26 C27 C28 179.6(2) . . . . ?
C26 C27 C28 C29 -0.2(4) . . . . ?
C27 C28 C29 C30 0.5(4) . . . . ?
C28 C29 C30 C31 0.7(4) . . . . ?
C29 C30 C31 C26 -2.2(4) . . . . ?
C29 C30 C31 C32 176.8(3) . . . . ?
C27 C26 C31 C30 2.6(4) . . . . ?
C1 C26 C31 C30 -178.3(2) . . . . ?
C27 C26 C31 C32 -176.6(2) . . . . ?
C1 C26 C31 C32 2.5(3) . . . . ?
C30 C31 C32 C37 -179.0(3) . . . . ?
C26 C31 C32 C37 0.1(3) . . . . ?
C30 C31 C32 C33 -0.3(5) . . . . ?
C26 C31 C32 C33 178.7(3) . . . . ?
C37 C32 C33 C34 0.1(4) . . . . ?
C31 C32 C33 C34 -178.4(2) . . . . ?
C32 C33 C34 C35 -0.1(4) . . . . ?
C33 C34 C35 C36 0.0(4) . . . . ?
C34 C35 C36 C37 0.1(4) . . . . ?
C35 C36 C37 C32 -0.1(4) . . . . ?
C35 C36 C37 C1 -178.3(2) . . . . ?
C33 C32 C37 C36 0.0(4) . . . . ?
C31 C32 C37 C36 178.8(2) . . . . ?
C33 C32 C37 C1 178.5(2) . . . . ?
C31 C32 C37 C1 -2.7(3) . . . . ?
C13 C1 C37 C36 -54.6(3) . . . . ?
C26 C1 C37 C36 -177.7(2) . . . . ?
C2 C1 C37 C36 62.1(3) . . . . ?
C13 C1 C37 C32 127.1(2) . . . . ?
C26 C1 C37 C32 3.9(3) . . . . ?
C2 C1 C37 C32 -116.3(2) . . . . ?



# END of CIF
####################################################################### 
# 
# 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_22019780sz_0m
_database_code_depnum_ccdc_archive 'CCDC 1987305'
loop_
_audit_author_name
_audit_author_address
jeannin
;university of rennes
France
;
_audit_update_record             
;
2020-02-29 deposited with the CCDC.	2020-04-24 downloaded from the CCDC.
;
_audit_creation_date             2019-07-16
_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        ?
_chemical_formula_moiety         'C43 H28'
_chemical_formula_sum            'C43 H28'
_chemical_formula_weight         544.65
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.2023(16)
_cell_length_b                   18.671(2)
_cell_length_c                   14.855(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.220(5)
_cell_angle_gamma                90
_cell_volume                     2951.3(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    299
_cell_measurement_theta_max      29.555
_cell_measurement_theta_min      2.887
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1086 before and 0.0671 after correction. The Ratio of minimum to maximum transmission is 0.9205. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            38725
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.056
_diffrn_reflns_theta_min         2.282
_diffrn_ambient_temperature      299.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5795
_reflns_number_total             8304
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.166
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         8304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      1.015
_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)+(0.0512P)²+0.4971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1352
_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:
 C8(H8), C20(H20), C16(H16), C26(H26), C18(H18), C29(H29), C27(H27), C11(H11),
 C23(H23), C24(H24), C15(H15), C36(H36), C28(H28), C33(H33), C43(H43), C12(H12),
  C5(H5), C40(H40), C13(H13), C35(H35), C1(H1), C34(H34), C14(H14), C42(H42),
 C41(H41), C4(H4), C3(H3), C2(H2)
;
_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
C8 C 0.71727(12) 0.54098(6) 0.51987(9) 0.0454(3) Uani 1 1 d . . . . .
H8 H 0.765760 0.536110 0.479578 0.054 Uiso 1 1 calc R . . . .
C21 C 0.29283(11) 0.59196(6) 0.72553(8) 0.0434(3) Uani 1 1 d . . . . .
C20 C 0.36767(12) 0.58905(6) 0.66724(8) 0.0444(3) Uani 1 1 d . . . . .
H20 H 0.337591 0.606255 0.605488 0.053 Uiso 1 1 calc R . . . .
C9 C 0.73064(12) 0.49142(6) 0.59221(9) 0.0441(3) Uani 1 1 d . . . . .
C25 C 0.16347(12) 0.61805(6) 0.70631(9) 0.0447(3) Uani 1 1 d . . . . .
C10 C 0.82529(12) 0.43330(7) 0.60830(8) 0.0465(3) Uani 1 1 d . . . . .
C30 C 0.12626(12) 0.60550(7) 0.78616(9) 0.0462(3) Uani 1 1 d . . . . .
C7 C 0.63290(12) 0.59773(6) 0.50641(9) 0.0452(3) Uani 1 1 d . . . . .
C16 C 0.65482(12) 0.49846(6) 0.65005(9) 0.0459(3) Uani 1 1 d . . . . .
H16 H 0.661375 0.464787 0.697489 0.055 Uiso 1 1 calc R . . . .
C22 C 0.33541(12) 0.56521(7) 0.81817(9) 0.0459(3) Uani 1 1 d . . . . .
C26 C 0.08182(13) 0.65059(7) 0.62673(10) 0.0523(3) Uani 1 1 d . . . . .
H26 H 0.107112 0.660029 0.573951 0.063 Uiso 1 1 calc R . . . .
C18 C 0.56031(12) 0.60379(7) 0.56666(9) 0.0469(3) Uani 1 1 d . . . . .
H18 H 0.504163 0.641740 0.558556 0.056 Uiso 1 1 calc R . . . .
C17 C 0.56946(12) 0.55440(6) 0.63901(9) 0.0442(3) Uani 1 1 d . . . . .
C32 C 0.26399(12) 0.61609(7) 0.95587(9) 0.0473(3) Uani 1 1 d . . . . .
C19 C 0.48865(12) 0.56020(6) 0.70123(9) 0.0443(3) Uani 1 1 d . . . . .
C37 C 0.22550(12) 0.58086(7) 1.02486(9) 0.0474(3) Uani 1 1 d . . . . .
C29 C 0.00664(13) 0.62366(8) 0.78626(10) 0.0550(3) Uani 1 1 d . . . . .
H29 H -0.018505 0.615037 0.839303 0.066 Uiso 1 1 calc R . . . .
C31 C 0.23324(12) 0.57122(7) 0.86554(9) 0.0469(3) Uani 1 1 d . . . . .
C39 C 0.19268(13) 0.50082(7) 0.89941(9) 0.0494(3) Uani 1 1 d . . . . .
C38 C 0.18391(12) 0.50861(7) 0.99045(9) 0.0482(3) Uani 1 1 d . . . . .
C6 C 0.62249(12) 0.65104(7) 0.42970(10) 0.0502(3) Uani 1 1 d . . . . .
C27 C -0.03793(13) 0.66880(8) 0.62712(11) 0.0578(3) Uani 1 1 d . . . . .
H27 H -0.093616 0.690453 0.574136 0.069 Uiso 1 1 calc R . . . .
C11 C 0.94194(13) 0.44582(8) 0.59684(10) 0.0565(3) Uani 1 1 d . . . . .
H11 H 0.960690 0.490968 0.578469 0.068 Uiso 1 1 calc R . . . .
C23 C 0.45514(13) 0.53689(8) 0.85262(9) 0.0529(3) Uani 1 1 d . . . . .
H23 H 0.484729 0.519262 0.914186 0.063 Uiso 1 1 calc R . . . .
C24 C 0.53027(13) 0.53505(7) 0.79460(9) 0.0515(3) Uani 1 1 d . . . . .
H24 H 0.611129 0.516509 0.818334 0.062 Uiso 1 1 calc R . . . .
C15 C 0.80114(14) 0.36540(7) 0.63673(11) 0.0588(3) Uani 1 1 d . . . . .
H15 H 0.723414 0.355565 0.644232 0.071 Uiso 1 1 calc R . . . .
C36 C 0.23134(15) 0.61507(9) 1.10906(10) 0.0607(4) Uani 1 1 d . . . . .
H36 H 0.202043 0.592574 1.153918 0.073 Uiso 1 1 calc R . . . .
C28 C -0.07514(13) 0.65496(8) 0.70589(11) 0.0607(4) Uani 1 1 d . . . . .
H28 H -0.156169 0.666821 0.704906 0.073 Uiso 1 1 calc R . . . .
C33 C 0.31520(15) 0.68370(8) 0.97280(11) 0.0613(4) Uani 1 1 d . . . . .
H33 H 0.343488 0.706856 0.927882 0.074 Uiso 1 1 calc R . . . .
C43 C 0.14431(15) 0.45162(8) 1.03369(11) 0.0626(4) Uani 1 1 d . . . . .
H43 H 0.137861 0.456446 1.094308 0.075 Uiso 1 1 calc R . . . .
C12 C 1.03067(15) 0.39155(10) 0.61257(11) 0.0678(4) Uani 1 1 d . . . . .
H12 H 1.107913 0.400489 0.603735 0.081 Uiso 1 1 calc R . . . .
C5 C 0.62293(14) 0.62944(9) 0.34014(10) 0.0619(4) Uani 1 1 d . . . . .
H5 H 0.628373 0.580943 0.327663 0.074 Uiso 1 1 calc R . . . .
C40 C 0.16281(17) 0.43703(8) 0.85164(11) 0.0683(4) Uani 1 1 d . . . . .
H40 H 0.168706 0.431897 0.790905 0.082 Uiso 1 1 calc R . . . .
C13 C 1.00586(16) 0.32509(9) 0.64091(11) 0.0681(4) Uani 1 1 d . . . . .
H13 H 1.065754 0.288950 0.651199 0.082 Uiso 1 1 calc R . . . .
C35 C 0.28159(17) 0.68323(9) 1.12488(11) 0.0730(4) Uani 1 1 d . . . . .
H35 H 0.286938 0.706782 1.181177 0.088 Uiso 1 1 calc R . . . .
C1 C 0.61318(17) 0.72349(8) 0.44612(13) 0.0723(4) Uani 1 1 d . . . . .
H1 H 0.611904 0.739102 0.505266 0.087 Uiso 1 1 calc R . . . .
C34 C 0.32363(18) 0.71639(9) 1.05811(12) 0.0743(5) Uani 1 1 d . . . . .
H34 H 0.358620 0.761918 1.070482 0.089 Uiso 1 1 calc R . . . .
C14 C 0.89190(17) 0.31210(8) 0.65406(12) 0.0704(4) Uani 1 1 d . . . . .
H14 H 0.875360 0.267262 0.674720 0.084 Uiso 1 1 calc R . . . .
C42 C 0.11473(17) 0.38790(9) 0.98571(13) 0.0742(5) Uani 1 1 d . . . . .
H42 H 0.088332 0.349321 1.014270 0.089 Uiso 1 1 calc R . . . .
C41 C 0.12366(19) 0.38043(9) 0.89594(14) 0.0790(5) Uani 1 1 d . . . . .
H41 H 0.103173 0.336864 0.864550 0.095 Uiso 1 1 calc R . . . .
C4 C 0.61540(18) 0.67896(11) 0.26953(12) 0.0804(5) Uani 1 1 d . . . . .
H4 H 0.615696 0.663737 0.209989 0.097 Uiso 1 1 calc R . . . .
C3 C 0.60745(19) 0.75088(12) 0.28732(15) 0.0907(6) Uani 1 1 d . . . . .
H3 H 0.603253 0.784330 0.240040 0.109 Uiso 1 1 calc R . . . .
C2 C 0.6057(2) 0.77306(10) 0.37477(17) 0.0926(6) Uani 1 1 d . . . . .
H2 H 0.599521 0.821618 0.386494 0.111 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C8 H8 0.9300 . ?
C8 C9 1.3902(17) . ?
C8 C7 1.3921(17) . ?
C21 C20 1.3819(16) . ?
C21 C25 1.4698(17) . ?
C21 C22 1.4001(17) . ?
C20 H20 0.9300 . ?
C20 C19 1.3978(18) . ?
C9 C10 1.4834(17) . ?
C9 C16 1.3905(17) . ?
C25 C30 1.3945(17) . ?
C25 C26 1.3882(18) . ?
C10 C11 1.3894(19) . ?
C10 C15 1.3894(19) . ?
C30 C29 1.3828(18) . ?
C30 C31 1.5338(18) . ?
C7 C18 1.3892(17) . ?
C7 C6 1.4899(17) . ?
C16 H16 0.9300 . ?
C16 C17 1.3908(17) . ?
C22 C31 1.5236(17) . ?
C22 C23 1.3825(19) . ?
C26 H26 0.9300 . ?
C26 C27 1.3857(19) . ?
C18 H18 0.9300 . ?
C18 C17 1.3954(17) . ?
C17 C19 1.4862(16) . ?
C32 C37 1.3947(17) . ?
C32 C31 1.5272(18) . ?
C32 C33 1.3767(19) . ?
C19 C24 1.3989(17) . ?
C37 C38 1.4660(19) . ?
C37 C36 1.3876(18) . ?
C29 H29 0.9300 . ?
C29 C28 1.386(2) . ?
C31 C39 1.5265(18) . ?
C39 C38 1.3940(18) . ?
C39 C40 1.373(2) . ?
C38 C43 1.3856(18) . ?
C6 C5 1.392(2) . ?
C6 C1 1.384(2) . ?
C27 H27 0.9300 . ?
C27 C28 1.384(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.3807(18) . ?
C24 H24 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.388(2) . ?
C36 H36 0.9300 . ?
C36 C35 1.382(2) . ?
C28 H28 0.9300 . ?
C33 H33 0.9300 . ?
C33 C34 1.383(2) . ?
C43 H43 0.9300 . ?
C43 C42 1.373(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.366(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.381(2) . ?
C40 H40 0.9300 . ?
C40 C41 1.387(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(2) . ?
C35 H35 0.9300 . ?
C35 C34 1.372(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.390(2) . ?
C34 H34 0.9300 . ?
C14 H14 0.9300 . ?
C42 H42 0.9300 . ?
C42 C41 1.375(2) . ?
C41 H41 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.377(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.369(3) . ?
C2 H2 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C8 H8 119.3 . . ?
C9 C8 C7 121.45(11) . . ?
C7 C8 H8 119.3 . . ?
C20 C21 C25 130.23(11) . . ?
C20 C21 C22 120.99(11) . . ?
C22 C21 C25 108.74(10) . . ?
C21 C20 H20 120.1 . . ?
C21 C20 C19 119.89(11) . . ?
C19 C20 H20 120.1 . . ?
C8 C9 C10 120.68(11) . . ?
C8 C9 C16 118.41(11) . . ?
C16 C9 C10 120.90(11) . . ?
C30 C25 C21 108.53(11) . . ?
C26 C25 C21 131.11(11) . . ?
C26 C25 C30 120.35(12) . . ?
C11 C10 C9 120.63(12) . . ?
C11 C10 C15 118.09(12) . . ?
C15 C10 C9 121.28(12) . . ?
C25 C30 C31 110.77(11) . . ?
C29 C30 C25 120.48(12) . . ?
C29 C30 C31 128.75(11) . . ?
C8 C7 C6 120.37(11) . . ?
C18 C7 C8 118.51(11) . . ?
C18 C7 C6 121.12(11) . . ?
C9 C16 H16 119.1 . . ?
C9 C16 C17 121.90(11) . . ?
C17 C16 H16 119.1 . . ?
C21 C22 C31 110.70(11) . . ?
C23 C22 C21 119.56(11) . . ?
C23 C22 C31 129.72(11) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 C25 119.00(13) . . ?
C27 C26 H26 120.5 . . ?
C7 C18 H18 119.1 . . ?
C7 C18 C17 121.71(11) . . ?
C17 C18 H18 119.1 . . ?
C16 C17 C18 117.99(11) . . ?
C16 C17 C19 120.76(11) . . ?
C18 C17 C19 121.24(11) . . ?
C37 C32 C31 110.50(11) . . ?
C33 C32 C37 120.34(12) . . ?
C33 C32 C31 129.06(12) . . ?
C20 C19 C17 120.91(11) . . ?
C20 C19 C24 118.19(11) . . ?
C24 C19 C17 120.87(11) . . ?
C32 C37 C38 108.38(11) . . ?
C36 C37 C32 120.46(13) . . ?
C36 C37 C38 131.15(12) . . ?
C30 C29 H29 120.6 . . ?
C30 C29 C28 118.82(13) . . ?
C28 C29 H29 120.6 . . ?
C22 C31 C30 101.23(9) . . ?
C22 C31 C32 116.77(11) . . ?
C22 C31 C39 115.65(11) . . ?
C32 C31 C30 110.73(10) . . ?
C39 C31 C30 111.79(11) . . ?
C39 C31 C32 101.03(10) . . ?
C38 C39 C31 110.39(11) . . ?
C40 C39 C31 128.76(12) . . ?
C40 C39 C38 120.81(13) . . ?
C39 C38 C37 108.86(11) . . ?
C43 C38 C37 131.15(13) . . ?
C43 C38 C39 119.96(13) . . ?
C5 C6 C7 120.98(12) . . ?
C1 C6 C7 120.68(13) . . ?
C1 C6 C5 118.34(13) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.37(13) . . ?
C28 C27 H27 119.8 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.55(14) . . ?
C12 C11 H11 119.7 . . ?
C22 C23 H23 120.4 . . ?
C24 C23 C22 119.25(12) . . ?
C24 C23 H23 120.4 . . ?
C19 C24 H24 119.0 . . ?
C23 C24 C19 122.10(12) . . ?
C23 C24 H24 119.0 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.64(14) . . ?
C14 C15 H15 119.7 . . ?
C37 C36 H36 120.7 . . ?
C35 C36 C37 118.63(14) . . ?
C35 C36 H36 120.7 . . ?
C29 C28 H28 119.5 . . ?
C27 C28 C29 120.95(13) . . ?
C27 C28 H28 119.5 . . ?
C32 C33 H33 120.7 . . ?
C32 C33 C34 118.51(14) . . ?
C34 C33 H33 120.7 . . ?
C38 C43 H43 120.5 . . ?
C42 C43 C38 119.02(14) . . ?
C42 C43 H43 120.5 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.74(15) . . ?
C13 C12 H12 119.6 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 120.96(16) . . ?
C4 C5 H5 119.5 . . ?
C39 C40 H40 120.7 . . ?
C39 C40 C41 118.55(15) . . ?
C41 C40 H40 120.7 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.50(14) . . ?
C14 C13 H13 120.3 . . ?
C36 C35 H35 119.8 . . ?
C34 C35 C36 120.43(14) . . ?
C34 C35 H35 119.8 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.41(17) . . ?
C2 C1 H1 119.8 . . ?
C33 C34 H34 119.2 . . ?
C35 C34 C33 121.53(15) . . ?
C35 C34 H34 119.2 . . ?
C15 C14 H14 119.8 . . ?
C13 C14 C15 120.46(15) . . ?
C13 C14 H14 119.8 . . ?
C43 C42 H42 119.6 . . ?
C43 C42 C41 120.82(14) . . ?
C41 C42 H42 119.6 . . ?
C40 C41 H41 119.6 . . ?
C42 C41 C40 120.84(16) . . ?
C42 C41 H41 119.6 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 119.97(18) . . ?
C3 C4 H4 120.0 . . ?
C4 C3 H3 120.1 . . ?
C2 C3 C4 119.86(16) . . ?
C2 C3 H3 120.1 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.46(18) . . ?
C3 C2 H2 119.8 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
