# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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. 
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data_cu_jpu_463_3r_jahn
_database_code_depnum_ccdc_archive 'CCDC 1484493'
_audit_update_record             
;
2017-11-21 deposited with the CCDC.
2017-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 Cl2 O2'
_chemical_formula_sum            'C30 H24 Cl2 O2'
_chemical_formula_weight         487.39
_chemical_compound_source        'synthesized by the authors'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   15.2712(5)
_cell_length_b                   11.6024(4)
_cell_length_c                   14.6920(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.1430(10)
_cell_angle_gamma                90
_cell_volume                     2487.51(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9884
_cell_measurement_theta_min      3.0283
_cell_measurement_theta_max      72.3516

_exptl_crystal_description       bar
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.541
_shelx_estimated_absorpt_T_min   0.644
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6494
_exptl_absorpt_correction_T_max  0.9231
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'

_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            31092
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.028
_diffrn_reflns_theta_max         72.344
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4889
_reflns_number_gt                3984
_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       'Bruker Instrument Service v4.2.9'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc.)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+1.1376P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4889
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0910
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
Cl1 Cl 0.11094(3) 0.54779(4) 0.02771(3) 0.04205(13) Uani 1 1 d . . . . .
Cl1' Cl 1.11492(3) 0.75604(6) 0.29100(4) 0.0708(2) Uani 1 1 d . . . . .
O1 O 0.57340(8) 0.41645(10) 0.29589(9) 0.0361(3) Uani 1 1 d . . . . .
O1' O 0.67805(8) 0.69093(10) 0.38931(9) 0.0358(3) Uani 1 1 d . . . . .
C1 C 0.46605(10) 0.54350(13) 0.32942(11) 0.0243(3) Uani 1 1 d . . . . .
C1' C 0.79012(10) 0.54617(13) 0.41019(11) 0.0252(3) Uani 1 1 d . . . . .
C2 C 0.43767(11) 0.45904(14) 0.38221(12) 0.0299(4) Uani 1 1 d . . . . .
H2 H 0.465200 0.384878 0.388907 0.036 Uiso 1 1 calc R U . . .
C2' C 0.83144(11) 0.57970(16) 0.50491(12) 0.0335(4) Uani 1 1 d . . . . .
H2' H 0.811646 0.647848 0.528817 0.040 Uiso 1 1 calc R U . . .
C3 C 0.37007(12) 0.48179(16) 0.42489(13) 0.0368(4) Uani 1 1 d . . . . .
H3 H 0.351122 0.423453 0.460367 0.044 Uiso 1 1 calc R U . . .
C3' C 0.90067(12) 0.51408(19) 0.56339(12) 0.0422(5) Uani 1 1 d . . . . .
H3' H 0.928302 0.537137 0.627498 0.051 Uiso 1 1 calc R U . . .
C4 C 0.33014(13) 0.58977(17) 0.41574(14) 0.0422(4) Uani 1 1 d . . . . .
H4 H 0.283362 0.605583 0.444611 0.051 Uiso 1 1 calc R U . . .
C4' C 0.93004(12) 0.41505(18) 0.52929(13) 0.0404(4) Uani 1 1 d . . . . .
H4' H 0.977601 0.370014 0.570028 0.048 Uiso 1 1 calc R U . . .
C5 C 0.35825(13) 0.67470(16) 0.36462(15) 0.0432(5) Uani 1 1 d . . . . .
H5 H 0.330980 0.748977 0.358999 0.052 Uiso 1 1 calc R U . . .
C5' C 0.89055(11) 0.38144(16) 0.43642(13) 0.0366(4) Uani 1 1 d . . . . .
H5' H 0.911236 0.313603 0.412949 0.044 Uiso 1 1 calc R U . . .
C6 C 0.42608(11) 0.65239(15) 0.32136(13) 0.0335(4) Uani 1 1 d . . . . .
H6 H 0.445114 0.711231 0.286395 0.040 Uiso 1 1 calc R U . . .
C6' C 0.82050(11) 0.44655(14) 0.37697(12) 0.0307(4) Uani 1 1 d . . . . .
H6' H 0.793158 0.422674 0.313025 0.037 Uiso 1 1 calc R U . . .
C7 C 0.53818(10) 0.51193(13) 0.28378(11) 0.0252(3) Uani 1 1 d . . . . .
C7' C 0.71235(10) 0.61665(13) 0.35163(11) 0.0247(3) Uani 1 1 d . . . . .
C8 C 0.56747(10) 0.59682(13) 0.21885(11) 0.0242(3) Uani 1 1 d . . . . .
H8 H 0.545078 0.675620 0.228274 0.029 Uiso 1 1 calc R U . . .
C8' C 0.67323(10) 0.59884(13) 0.24422(11) 0.0245(3) Uani 1 1 d . . . . .
H8' H 0.695645 0.524035 0.225647 0.029 Uiso 1 1 calc R U . . .
C9 C 0.52251(10) 0.55878(15) 0.11490(11) 0.0302(4) Uani 1 1 d . . . . .
H9A H 0.540777 0.612832 0.071615 0.036 Uiso 1 1 calc R U . . .
H9B H 0.545424 0.481252 0.105366 0.036 Uiso 1 1 calc R U . . .
C9' C 0.70519(11) 0.69941(16) 0.19258(13) 0.0345(4) Uani 1 1 d . . . . .
H9'1 H 0.679935 0.687606 0.123004 0.041 Uiso 1 1 calc R U . . .
H9'2 H 0.679122 0.772088 0.208599 0.041 Uiso 1 1 calc R U . . .
C10 C 0.41888(10) 0.55533(14) 0.08909(11) 0.0258(3) Uani 1 1 d . . . . .
C10' C 0.80789(10) 0.71279(14) 0.21680(11) 0.0283(3) Uani 1 1 d . . . . .
C11 C 0.37259(10) 0.45164(14) 0.08430(11) 0.0278(3) Uani 1 1 d . . . . .
H11 H 0.406236 0.381541 0.094758 0.033 Uiso 1 1 calc R U . . .
C11' C 0.85209(12) 0.80326(15) 0.27359(13) 0.0373(4) Uani 1 1 d . . . . .
H11' H 0.817143 0.856860 0.297301 0.045 Uiso 1 1 calc R U . . .
C12 C 0.27802(11) 0.44846(14) 0.06451(11) 0.0290(3) Uani 1 1 d . . . . .
H12 H 0.246841 0.376968 0.060777 0.035 Uiso 1 1 calc R U . . .
C12' C 0.94610(13) 0.81710(17) 0.29645(14) 0.0429(5) Uani 1 1 d . . . . .
H12' H 0.975520 0.878929 0.336164 0.051 Uiso 1 1 calc R U . . .
C13 C 0.23003(10) 0.55088(14) 0.05034(12) 0.0299(4) Uani 1 1 d . . . . .
C13' C 0.99628(11) 0.74058(18) 0.26114(13) 0.0395(4) Uani 1 1 d . . . . .
C14 C 0.27386(11) 0.65564(15) 0.05407(13) 0.0352(4) Uani 1 1 d . . . . .
H14 H 0.239934 0.725527 0.043570 0.042 Uiso 1 1 calc R U . . .
C14' C 0.95494(12) 0.65035(17) 0.20366(13) 0.0393(4) Uani 1 1 d . . . . .
H14' H 0.990255 0.598304 0.178965 0.047 Uiso 1 1 calc R U . . .
C15 C 0.36823(11) 0.65676(15) 0.07344(13) 0.0334(4) Uani 1 1 d . . . . .
H15 H 0.399026 0.728390 0.076083 0.040 Uiso 1 1 calc R U . . .
C15' C 0.86071(11) 0.63667(16) 0.18235(12) 0.0347(4) Uani 1 1 d . . . . .
H15' H 0.831809 0.573965 0.143422 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
Cl1 C13 1.7500(15) . ?
Cl1' C13' 1.7431(17) . ?
O1 C7 1.2214(19) . ?
O1' C7' 1.2225(19) . ?
C1 C6 1.393(2) . ?
C1 C2 1.396(2) . ?
C1 C7 1.494(2) . ?
C1' C6' 1.387(2) . ?
C1' C2' 1.403(2) . ?
C1' C7' 1.489(2) . ?
C2 C3 1.382(2) . ?
C2 H2 0.9500 . ?
C2' C3' 1.378(3) . ?
C2' H2' 0.9500 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9500 . ?
C3' C4' 1.380(3) . ?
C3' H3' 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C4' C5' 1.376(3) . ?
C4' H4' 0.9500 . ?
C5 C6 1.390(2) . ?
C5 H5 0.9500 . ?
C5' C6' 1.388(2) . ?
C5' H5' 0.9500 . ?
C6 H6 0.9500 . ?
C6' H6' 0.9500 . ?
C7 C8 1.527(2) . ?
C7' C8' 1.528(2) . ?
C8 C9 1.543(2) . ?
C8 C8' 1.5470(19) . ?
C8 H8 1.0000 . ?
C8' C9' 1.547(2) . ?
C8' H8' 1.0000 . ?
C9 C10 1.515(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9' C10' 1.510(2) . ?
C9' H9'1 0.9900 . ?
C9' H9'2 0.9900 . ?
C10 C11 1.387(2) . ?
C10 C15 1.390(2) . ?
C10' C11' 1.386(2) . ?
C10' C15' 1.388(2) . ?
C11 C12 1.387(2) . ?
C11 H11 0.9500 . ?
C11' C12' 1.384(2) . ?
C11' H11' 0.9500 . ?
C12 C13 1.379(2) . ?
C12 H12 0.9500 . ?
C12' C13' 1.371(3) . ?
C12' H12' 0.9500 . ?
C13 C14 1.381(2) . ?
C13' C14' 1.376(3) . ?
C14 C15 1.384(2) . ?
C14 H14 0.9500 . ?
C14' C15' 1.389(2) . ?
C14' H14' 0.9500 . ?
C15 H15 0.9500 . ?
C15' H15' 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
C6 C1 C2 118.95(14) . . ?
C6 C1 C7 123.15(14) . . ?
C2 C1 C7 117.91(14) . . ?
C6' C1' C2' 118.75(15) . . ?
C6' C1' C7' 123.16(14) . . ?
C2' C1' C7' 118.02(15) . . ?
C3 C2 C1 120.92(16) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C3' C2' C1' 120.21(17) . . ?
C3' C2' H2' 119.9 . . ?
C1' C2' H2' 119.9 . . ?
C2 C3 C4 119.74(16) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C2' C3' C4' 120.35(17) . . ?
C2' C3' H3' 119.8 . . ?
C4' C3' H3' 119.8 . . ?
C5 C4 C3 120.02(16) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5' C4' C3' 120.11(16) . . ?
C5' C4' H4' 119.9 . . ?
C3' C4' H4' 119.9 . . ?
C4 C5 C6 120.56(17) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C4' C5' C6' 120.07(17) . . ?
C4' C5' H5' 120.0 . . ?
C6' C5' H5' 120.0 . . ?
C5 C6 C1 119.80(16) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C1' C6' C5' 120.52(16) . . ?
C1' C6' H6' 119.7 . . ?
C5' C6' H6' 119.7 . . ?
O1 C7 C1 120.55(14) . . ?
O1 C7 C8 118.59(13) . . ?
C1 C7 C8 120.84(13) . . ?
O1' C7' C1' 120.05(14) . . ?
O1' C7' C8' 118.28(14) . . ?
C1' C7' C8' 121.67(13) . . ?
C7 C8 C9 107.88(12) . . ?
C7 C8 C8' 109.67(12) . . ?
C9 C8 C8' 111.79(12) . . ?
C7 C8 H8 109.2 . . ?
C9 C8 H8 109.2 . . ?
C8' C8 H8 109.2 . . ?
C7' C8' C8 108.27(12) . . ?
C7' C8' C9' 108.71(13) . . ?
C8 C8' C9' 110.56(12) . . ?
C7' C8' H8' 109.8 . . ?
C8 C8' H8' 109.8 . . ?
C9' C8' H8' 109.8 . . ?
C10 C9 C8 112.49(13) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C10' C9' C8' 114.69(13) . . ?
C10' C9' H9'1 108.6 . . ?
C8' C9' H9'1 108.6 . . ?
C10' C9' H9'2 108.6 . . ?
C8' C9' H9'2 108.6 . . ?
H9'1 C9' H9'2 107.6 . . ?
C11 C10 C15 118.41(14) . . ?
C11 C10 C9 120.99(14) . . ?
C15 C10 C9 120.55(14) . . ?
C11' C10' C15' 117.96(15) . . ?
C11' C10' C9' 120.48(16) . . ?
C15' C10' C9' 121.56(16) . . ?
C10 C11 C12 121.16(15) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C12' C11' C10' 121.34(17) . . ?
C12' C11' H11' 119.3 . . ?
C10' C11' H11' 119.3 . . ?
C13 C12 C11 118.87(15) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C13' C12' C11' 119.26(18) . . ?
C13' C12' H12' 120.4 . . ?
C11' C12' H12' 120.4 . . ?
C12 C13 C14 121.50(14) . . ?
C12 C13 Cl1 119.16(12) . . ?
C14 C13 Cl1 119.34(12) . . ?
C12' C13' C14' 121.23(16) . . ?
C12' C13' Cl1' 119.58(15) . . ?
C14' C13' Cl1' 119.18(16) . . ?
C13 C14 C15 118.65(15) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C13' C14' C15' 118.87(17) . . ?
C13' C14' H14' 120.6 . . ?
C15' C14' H14' 120.6 . . ?
C14 C15 C10 121.40(15) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
C10' C15' C14' 121.33(17) . . ?
C10' C15' H15' 119.3 . . ?
C14' C15' H15' 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.9(2) . . . . ?
C7 C1 C2 C3 -178.84(15) . . . . ?
C6' C1' C2' C3' -0.2(2) . . . . ?
C7' C1' C2' C3' 176.80(15) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C1' C2' C3' C4' 0.1(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C2' C3' C4' C5' 0.3(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C3' C4' C5' C6' -0.5(3) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C7 C1 C6 C5 178.95(16) . . . . ?
C2' C1' C6' C5' -0.1(2) . . . . ?
C7' C1' C6' C5' -176.92(15) . . . . ?
C4' C5' C6' C1' 0.4(3) . . . . ?
C6 C1 C7 O1 177.35(15) . . . . ?
C2 C1 C7 O1 -2.9(2) . . . . ?
C6 C1 C7 C8 -4.4(2) . . . . ?
C2 C1 C7 C8 175.35(14) . . . . ?
C6' C1' C7' O1' 166.82(15) . . . . ?
C2' C1' C7' O1' -10.1(2) . . . . ?
C6' C1' C7' C8' -13.1(2) . . . . ?
C2' C1' C7' C8' 170.03(13) . . . . ?
O1 C7 C8 C9 75.17(17) . . . . ?
C1 C7 C8 C9 -103.09(15) . . . . ?
O1 C7 C8 C8' -46.80(19) . . . . ?
C1 C7 C8 C8' 134.93(14) . . . . ?
O1' C7' C8' C8 -45.61(18) . . . . ?
C1' C7' C8' C8 134.31(14) . . . . ?
O1' C7' C8' C9' 74.54(17) . . . . ?
C1' C7' C8' C9' -105.54(15) . . . . ?
C7 C8 C8' C7' -50.71(16) . . . . ?
C9 C8 C8' C7' -170.32(13) . . . . ?
C7 C8 C8' C9' -169.69(13) . . . . ?
C9 C8 C8' C9' 70.70(17) . . . . ?
C7 C8 C9 C10 58.85(17) . . . . ?
C8' C8 C9 C10 179.51(13) . . . . ?
C7' C8' C9' C10' 58.17(19) . . . . ?
C8 C8' C9' C10' 176.89(14) . . . . ?
C8 C9 C10 C11 -102.61(17) . . . . ?
C8 C9 C10 C15 74.75(19) . . . . ?
C8' C9' C10' C11' -107.24(18) . . . . ?
C8' C9' C10' C15' 73.6(2) . . . . ?
C15 C10 C11 C12 -0.1(2) . . . . ?
C9 C10 C11 C12 177.35(15) . . . . ?
C15' C10' C11' C12' -0.7(3) . . . . ?
C9' C10' C11' C12' -179.90(16) . . . . ?
C10 C11 C12 C13 -0.6(2) . . . . ?
C10' C11' C12' C13' 0.9(3) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
C11 C12 C13 Cl1 -178.73(12) . . . . ?
C11' C12' C13' C14' -0.1(3) . . . . ?
C11' C12' C13' Cl1' -179.04(14) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
Cl1 C13 C14 C15 179.06(14) . . . . ?
C12' C13' C14' C15' -0.7(3) . . . . ?
Cl1' C13' C14' C15' 178.20(14) . . . . ?
C13 C14 C15 C10 -0.1(3) . . . . ?
C11 C10 C15 C14 0.4(3) . . . . ?
C9 C10 C15 C14 -177.01(16) . . . . ?
C11' C10' C15' C14' -0.1(3) . . . . ?
C9' C10' C15' C14' 179.02(16) . . . . ?
C13' C14' C15' C10' 0.9(3) . . . . ?

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_cu_jp_536_1_2_rr_jahn
_database_code_depnum_ccdc_archive 'CCDC 1538562'
_audit_update_record             
;
2017-03-16 deposited with the CCDC.
2017-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H30 O2'
_chemical_formula_sum            'C24 H30 O2'
_chemical_formula_weight         350.48
_chemical_compound_source        'synthesized by the authors'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   14.8423(4)
_cell_length_b                   16.4382(5)
_cell_length_c                   12.5460(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.0660(10)
_cell_angle_gamma                90
_cell_volume                     3037.73(16)
_cell_formula_units_Z            6
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      3.0001
_cell_measurement_theta_max      72.2001

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_F_000             1140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.151
_exptl_absorpt_coefficient_mu    0.550
_shelx_estimated_absorpt_T_min   0.885
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37226
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.000
_diffrn_reflns_theta_max         72.323
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5982
_reflns_number_gt                4778
_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       'Bruker Instrument Service v4.2.9'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²+1.3697P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00173(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5982
_refine_ls_number_parameters     356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.0995
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
C1A C 0.70918(9) 0.98504(9) 0.50131(11) 0.0250(3) Uani 1 1 d . . . . .
C2A C 0.77091(10) 0.92539(10) 0.47878(12) 0.0299(3) Uani 1 1 d . . . . .
H2A H 0.7548 0.8696 0.4820 0.036 Uiso 1 1 calc R U . . .
C3A C 0.85533(11) 0.94664(11) 0.45179(13) 0.0360(4) Uani 1 1 d . . . . .
H3A H 0.8968 0.9055 0.4362 0.043 Uiso 1 1 calc R U . . .
C4A C 0.87960(10) 1.02810(11) 0.44744(12) 0.0348(4) Uani 1 1 d . . . . .
H4A H 0.9377 1.0427 0.4293 0.042 Uiso 1 1 calc R U . . .
C5A C 0.81902(10) 1.08789(10) 0.46953(11) 0.0303(3) Uani 1 1 d . . . . .
H5A H 0.8356 1.1436 0.4667 0.036 Uiso 1 1 calc R U . . .
C6A C 0.73383(10) 1.06665(9) 0.49593(11) 0.0265(3) Uani 1 1 d . . . . .
H6A H 0.6922 1.1079 0.5104 0.032 Uiso 1 1 calc R U . . .
C7A C 0.62056(10) 0.95788(9) 0.53428(11) 0.0263(3) Uani 1 1 d . . . . .
C8A C 0.54146(9) 1.01705(9) 0.53638(11) 0.0263(3) Uani 1 1 d . . . . .
H8A H 0.5585 1.0710 0.5079 0.032 Uiso 1 1 calc R U . . .
C9A C 0.52288(10) 1.02718(10) 0.65367(12) 0.0317(3) Uani 1 1 d . . . . .
H9A1 H 0.4689 1.0624 0.6553 0.038 Uiso 1 1 calc R U . . .
H9A2 H 0.5086 0.9733 0.6825 0.038 Uiso 1 1 calc R U . . .
C10A C 0.60271(12) 1.06424(11) 0.72638(13) 0.0390(4) Uani 1 1 d . . . . .
H10A H 0.6571 1.0300 0.7223 0.047 Uiso 1 1 calc R U . . .
H10B H 0.6156 1.1188 0.6984 0.047 Uiso 1 1 calc R U . . .
C11A C 0.58752(13) 1.07258(12) 0.84390(14) 0.0478(5) Uani 1 1 d . . . . .
H11A H 0.6361 1.1072 0.8812 0.057 Uiso 1 1 calc R U . . .
H11B H 0.5289 1.1005 0.8476 0.057 Uiso 1 1 calc R U . . .
C12A C 0.5867(2) 0.99355(16) 0.90129(17) 0.0740(7) Uani 1 1 d . . . . .
H12A H 0.5363 0.9601 0.8678 0.111 Uiso 1 1 calc R U . . .
H12B H 0.5791 1.0033 0.9767 0.111 Uiso 1 1 calc R U . . .
H12C H 0.6442 0.9651 0.8972 0.111 Uiso 1 1 calc R U . . .
O1A O 0.61118(7) 0.88735(7) 0.56157(9) 0.0336(3) Uani 1 1 d . . . . .
C1B C 0.36525(9) 0.70975(9) 0.34984(11) 0.0251(3) Uani 1 1 d . . . . .
C2B C 0.43542(11) 0.73137(10) 0.42878(13) 0.0359(4) Uani 1 1 d . . . . .
H2B H 0.4230 0.7390 0.5006 0.043 Uiso 1 1 calc R U . . .
C3B C 0.52260(11) 0.74184(11) 0.40404(15) 0.0434(4) Uani 1 1 d . . . . .
H3B H 0.5698 0.7575 0.4583 0.052 Uiso 1 1 calc R U . . .
C4B C 0.54110(11) 0.72937(11) 0.29992(15) 0.0401(4) Uani 1 1 d . . . . .
H4B H 0.6009 0.7374 0.2824 0.048 Uiso 1 1 calc R U . . .
C5B C 0.47290(11) 0.70531(11) 0.22122(14) 0.0378(4) Uani 1 1 d . . . . .
H5B H 0.4864 0.6950 0.1504 0.045 Uiso 1 1 calc R U . . .
C6B C 0.38469(10) 0.69623(10) 0.24556(12) 0.0312(3) Uani 1 1 d . . . . .
H6B H 0.3376 0.6808 0.1911 0.037 Uiso 1 1 calc R U . . .
C7B C 0.27194(10) 0.70327(9) 0.38258(11) 0.0255(3) Uani 1 1 d . . . . .
C8B C 0.19186(9) 0.67445(9) 0.30404(11) 0.0243(3) Uani 1 1 d . . . . .
H8B H 0.2096 0.6749 0.2297 0.029 Uiso 1 1 calc R U . . .
C9B C 0.16872(10) 0.58671(9) 0.33400(12) 0.0298(3) Uani 1 1 d . . . . .
H9B1 H 0.1546 0.5860 0.4091 0.036 Uiso 1 1 calc R U . . .
H9B2 H 0.1135 0.5691 0.2873 0.036 Uiso 1 1 calc R U . . .
C10B C 0.24464(10) 0.52581(9) 0.32323(12) 0.0300(3) Uani 1 1 d . . . . .
H10C H 0.2614 0.5286 0.2493 0.036 Uiso 1 1 calc R U . . .
H10D H 0.2987 0.5413 0.3733 0.036 Uiso 1 1 calc R U . . .
C11B C 0.21840(12) 0.43899(10) 0.34674(14) 0.0365(4) Uani 1 1 d . . . . .
H11C H 0.1634 0.4240 0.2978 0.044 Uiso 1 1 calc R U . . .
H11D H 0.2031 0.4359 0.4213 0.044 Uiso 1 1 calc R U . . .
C12B C 0.29312(13) 0.37806(11) 0.33347(15) 0.0434(4) Uani 1 1 d . . . . .
H12D H 0.3077 0.3798 0.2594 0.065 Uiso 1 1 calc R U . . .
H12E H 0.2726 0.3233 0.3495 0.065 Uiso 1 1 calc R U . . .
H12F H 0.3474 0.3918 0.3829 0.065 Uiso 1 1 calc R U . . .
C13B C -0.05896(9) 0.69681(8) 0.30252(11) 0.0232(3) Uani 1 1 d . . . . .
C14B C -0.13821(10) 0.67034(9) 0.24094(12) 0.0277(3) Uani 1 1 d . . . . .
H14B H -0.1370 0.6571 0.1674 0.033 Uiso 1 1 calc R U . . .
C15B C -0.21852(10) 0.66320(10) 0.28560(13) 0.0335(4) Uani 1 1 d . . . . .
H15B H -0.2721 0.6452 0.2430 0.040 Uiso 1 1 calc R U . . .
C16B C -0.22045(10) 0.68252(10) 0.39297(13) 0.0342(4) Uani 1 1 d . . . . .
H16B H -0.2755 0.6778 0.4239 0.041 Uiso 1 1 calc R U . . .
C17B C -0.14247(10) 0.70859(10) 0.45503(12) 0.0317(3) Uani 1 1 d . . . . .
H17B H -0.1440 0.7217 0.5285 0.038 Uiso 1 1 calc R U . . .
C18B C -0.06191(10) 0.71568(9) 0.41037(12) 0.0274(3) Uani 1 1 d . . . . .
H18B H -0.0084 0.7335 0.4535 0.033 Uiso 1 1 calc R U . . .
C19B C 0.02526(9) 0.70333(9) 0.24811(11) 0.0236(3) Uani 1 1 d . . . . .
C20B C 0.11311(9) 0.73481(9) 0.30970(11) 0.0239(3) Uani 1 1 d . . . . .
H20B H 0.1038 0.7425 0.3866 0.029 Uiso 1 1 calc R U . . .
C21B C 0.13428(10) 0.81766(9) 0.26217(12) 0.0272(3) Uani 1 1 d . . . . .
H21A H 0.1920 0.8384 0.3004 0.033 Uiso 1 1 calc R U . . .
H21B H 0.1428 0.8103 0.1857 0.033 Uiso 1 1 calc R U . . .
C22B C 0.06001(10) 0.88088(9) 0.26983(13) 0.0309(3) Uani 1 1 d . . . . .
H22A H 0.0043 0.8633 0.2241 0.037 Uiso 1 1 calc R U . . .
H22B H 0.0460 0.8831 0.3449 0.037 Uiso 1 1 calc R U . . .
C23B C 0.08538(11) 0.96580(10) 0.23565(13) 0.0355(4) Uani 1 1 d . . . . .
H23A H 0.0364 1.0041 0.2485 0.043 Uiso 1 1 calc R U . . .
H23B H 0.1415 0.9833 0.2808 0.043 Uiso 1 1 calc R U . . .
C24B C 0.10053(16) 0.97059(12) 0.11853(15) 0.0541(5) Uani 1 1 d . . . . .
H24A H 0.1545 0.9390 0.1073 0.081 Uiso 1 1 calc R U . . .
H24B H 0.1093 1.0275 0.0989 0.081 Uiso 1 1 calc R U . . .
H24C H 0.0475 0.9484 0.0737 0.081 Uiso 1 1 calc R U . . .
O1B O 0.25962(7) 0.71994(8) 0.47447(8) 0.0376(3) Uani 1 1 d . . . . .
O2B O 0.02293(7) 0.68605(7) 0.15304(8) 0.0324(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A C2A 1.394(2) . ?
C1A C6A 1.394(2) . ?
C1A C7A 1.495(2) . ?
C2A C3A 1.382(2) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.389(2) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.383(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.390(2) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A O1A 1.2217(18) . ?
C7A C8A 1.527(2) . ?
C8A C9A 1.539(2) . ?
C8A C8A 1.545(3) 3_676 ?
C8A H8A 1.0000 . ?
C9A C10A 1.530(2) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10A C11A 1.525(2) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A C12A 1.486(3) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C1B C6B 1.392(2) . ?
C1B C2B 1.392(2) . ?
C1B C7B 1.496(2) . ?
C2B C3B 1.378(2) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.383(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.382(2) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.388(2) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B O1B 1.2205(17) . ?
C7B C8B 1.5231(19) . ?
C8B C9B 1.540(2) . ?
C8B C20B 1.5413(19) . ?
C8B H8B 1.0000 . ?
C9B C10B 1.526(2) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
C10B C11B 1.518(2) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B C12B 1.519(2) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13B C18B 1.394(2) . ?
C13B C14B 1.395(2) . ?
C13B C19B 1.5001(19) . ?
C14B C15B 1.383(2) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.388(2) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.381(2) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.386(2) . ?
C17B H17B 0.9500 . ?
C18B H18B 0.9500 . ?
C19B O2B 1.2225(17) . ?
C19B C20B 1.5221(19) . ?
C20B C21B 1.535(2) . ?
C20B H20B 1.0000 . ?
C21B C22B 1.527(2) . ?
C21B H21A 0.9900 . ?
C21B H21B 0.9900 . ?
C22B C23B 1.521(2) . ?
C22B H22A 0.9900 . ?
C22B H22B 0.9900 . ?
C23B C24B 1.516(2) . ?
C23B H23A 0.9900 . ?
C23B H23B 0.9900 . ?
C24B H24A 0.9800 . ?
C24B H24B 0.9800 . ?
C24B H24C 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
C2A C1A C6A 118.94(14) . . ?
C2A C1A C7A 117.94(14) . . ?
C6A C1A C7A 123.08(13) . . ?
C3A C2A C1A 120.66(15) . . ?
C3A C2A H2A 119.7 . . ?
C1A C2A H2A 119.7 . . ?
C2A C3A C4A 120.02(15) . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C5A C4A C3A 119.93(14) . . ?
C5A C4A H4A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C4A C5A C6A 120.13(15) . . ?
C4A C5A H5A 119.9 . . ?
C6A C5A H5A 119.9 . . ?
C5A C6A C1A 120.32(14) . . ?
C5A C6A H6A 119.8 . . ?
C1A C6A H6A 119.8 . . ?
O1A C7A C1A 119.70(13) . . ?
O1A C7A C8A 119.03(13) . . ?
C1A C7A C8A 121.27(13) . . ?
C7A C8A C9A 108.30(12) . . ?
C7A C8A C8A 108.47(15) . 3_676 ?
C9A C8A C8A 112.39(15) . 3_676 ?
C7A C8A H8A 109.2 . . ?
C9A C8A H8A 109.2 . . ?
C8A C8A H8A 109.2 3_676 . ?
C10A C9A C8A 113.35(13) . . ?
C10A C9A H9A1 108.9 . . ?
C8A C9A H9A1 108.9 . . ?
C10A C9A H9A2 108.9 . . ?
C8A C9A H9A2 108.9 . . ?
H9A1 C9A H9A2 107.7 . . ?
C11A C10A C9A 114.62(15) . . ?
C11A C10A H10A 108.6 . . ?
C9A C10A H10A 108.6 . . ?
C11A C10A H10B 108.6 . . ?
C9A C10A H10B 108.6 . . ?
H10A C10A H10B 107.6 . . ?
C12A C11A C10A 113.63(17) . . ?
C12A C11A H11A 108.8 . . ?
C10A C11A H11A 108.8 . . ?
C12A C11A H11B 108.8 . . ?
C10A C11A H11B 108.8 . . ?
H11A C11A H11B 107.7 . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C6B C1B C2B 119.08(14) . . ?
C6B C1B C7B 123.55(13) . . ?
C2B C1B C7B 117.36(13) . . ?
C3B C2B C1B 120.83(16) . . ?
C3B C2B H2B 119.6 . . ?
C1B C2B H2B 119.6 . . ?
C2B C3B C4B 119.69(15) . . ?
C2B C3B H3B 120.2 . . ?
C4B C3B H3B 120.2 . . ?
C5B C4B C3B 120.28(15) . . ?
C5B C4B H4B 119.9 . . ?
C3B C4B H4B 119.9 . . ?
C4B C5B C6B 120.08(15) . . ?
C4B C5B H5B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C5B C6B C1B 119.98(14) . . ?
C5B C6B H6B 120.0 . . ?
C1B C6B H6B 120.0 . . ?
O1B C7B C1B 119.65(13) . . ?
O1B C7B C8B 119.03(13) . . ?
C1B C7B C8B 121.31(12) . . ?
C7B C8B C9B 108.25(12) . . ?
C7B C8B C20B 107.81(11) . . ?
C9B C8B C20B 113.48(11) . . ?
C7B C8B H8B 109.1 . . ?
C9B C8B H8B 109.1 . . ?
C20B C8B H8B 109.1 . . ?
C10B C9B C8B 113.81(12) . . ?
C10B C9B H9B1 108.8 . . ?
C8B C9B H9B1 108.8 . . ?
C10B C9B H9B2 108.8 . . ?
C8B C9B H9B2 108.8 . . ?
H9B1 C9B H9B2 107.7 . . ?
C11B C10B C9B 112.94(13) . . ?
C11B C10B H10C 109.0 . . ?
C9B C10B H10C 109.0 . . ?
C11B C10B H10D 109.0 . . ?
C9B C10B H10D 109.0 . . ?
H10C C10B H10D 107.8 . . ?
C10B C11B C12B 112.98(14) . . ?
C10B C11B H11C 109.0 . . ?
C12B C11B H11C 109.0 . . ?
C10B C11B H11D 109.0 . . ?
C12B C11B H11D 109.0 . . ?
H11C C11B H11D 107.8 . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C18B C13B C14B 118.81(13) . . ?
C18B C13B C19B 123.59(13) . . ?
C14B C13B C19B 117.60(13) . . ?
C15B C14B C13B 120.80(14) . . ?
C15B C14B H14B 119.6 . . ?
C13B C14B H14B 119.6 . . ?
C14B C15B C16B 119.71(14) . . ?
C14B C15B H15B 120.1 . . ?
C16B C15B H15B 120.1 . . ?
C17B C16B C15B 120.15(14) . . ?
C17B C16B H16B 119.9 . . ?
C15B C16B H16B 119.9 . . ?
C16B C17B C18B 120.19(14) . . ?
C16B C17B H17B 119.9 . . ?
C18B C17B H17B 119.9 . . ?
C17B C18B C13B 120.34(14) . . ?
C17B C18B H18B 119.8 . . ?
C13B C18B H18B 119.8 . . ?
O2B C19B C13B 120.15(12) . . ?
O2B C19B C20B 119.60(12) . . ?
C13B C19B C20B 120.20(12) . . ?
C19B C20B C21B 107.94(11) . . ?
C19B C20B C8B 111.40(11) . . ?
C21B C20B C8B 111.14(11) . . ?
C19B C20B H20B 108.8 . . ?
C21B C20B H20B 108.8 . . ?
C8B C20B H20B 108.8 . . ?
C22B C21B C20B 113.31(12) . . ?
C22B C21B H21A 108.9 . . ?
C20B C21B H21A 108.9 . . ?
C22B C21B H21B 108.9 . . ?
C20B C21B H21B 108.9 . . ?
H21A C21B H21B 107.7 . . ?
C23B C22B C21B 113.65(13) . . ?
C23B C22B H22A 108.8 . . ?
C21B C22B H22A 108.8 . . ?
C23B C22B H22B 108.8 . . ?
C21B C22B H22B 108.8 . . ?
H22A C22B H22B 107.7 . . ?
C24B C23B C22B 113.10(14) . . ?
C24B C23B H23A 109.0 . . ?
C22B C23B H23A 109.0 . . ?
C24B C23B H23B 109.0 . . ?
C22B C23B H23B 109.0 . . ?
H23A C23B H23B 107.8 . . ?
C23B C24B H24A 109.5 . . ?
C23B C24B H24B 109.5 . . ?
H24A C24B H24B 109.5 . . ?
C23B C24B H24C 109.5 . . ?
H24A C24B H24C 109.5 . . ?
H24B C24B H24C 109.5 . . ?

_refine_diff_density_max         0.502
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_cu_jpu_456_2_jahn
_database_code_depnum_ccdc_archive 'CCDC 1538563'
_audit_update_record             
;
2017-03-16 deposited with the CCDC.
2017-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H26 O2'
_chemical_formula_sum            'C30 H26 O2'
_chemical_formula_weight         418.51
_chemical_compound_source        'synthesized by the authors'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.2432(2)
_cell_length_b                   10.4558(3)
_cell_length_c                   13.9905(4)
_cell_angle_alpha                89.4600(10)
_cell_angle_beta                 73.2660(10)
_cell_angle_gamma                88.8100(10)
_cell_volume                     1154.51(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      3.2986
_cell_measurement_theta_max      72.3971

_exptl_crystal_description       prism
_exptl_crystal_colour            coloutless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.121
_exptl_absorpt_coefficient_mu    0.575
_shelx_estimated_absorpt_T_min   0.870
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18313
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.299
_diffrn_reflns_theta_max         72.390
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4541
_reflns_number_gt                3867
_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       'Bruker Instrument Service v4.2.9'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0511P)²+0.2603P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0077(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4541
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
C1A C 0.54655(13) 0.74936(10) 0.38394(8) 0.0214(2) Uani 1 1 d . . . . .
C2A C 0.59618(14) 0.78716(11) 0.28405(8) 0.0248(3) Uani 1 1 d . . . . .
H2A H 0.6493 0.8671 0.2655 0.030 Uiso 1 1 calc R U . . .
C3A C 0.56783(15) 0.70759(13) 0.21154(9) 0.0307(3) Uani 1 1 d . . . . .
H3A H 0.6049 0.7318 0.1432 0.037 Uiso 1 1 calc R U . . .
C4A C 0.48545(16) 0.59305(13) 0.23918(10) 0.0337(3) Uani 1 1 d . . . . .
H4A H 0.4635 0.5400 0.1897 0.040 Uiso 1 1 calc R U . . .
C5A C 0.43490(16) 0.55530(12) 0.33832(10) 0.0344(3) Uani 1 1 d . . . . .
H5A H 0.3780 0.4768 0.3568 0.041 Uiso 1 1 calc R U . . .
C6A C 0.46755(15) 0.63225(11) 0.41042(9) 0.0272(3) Uani 1 1 d . . . . .
H6A H 0.4360 0.6052 0.4782 0.033 Uiso 1 1 calc R U . . .
C7A C 0.57881(13) 0.82842(11) 0.46468(8) 0.0217(2) Uani 1 1 d . . . . .
C8A C 0.57560(13) 0.97438(10) 0.45704(8) 0.0212(2) Uani 1 1 d . . . . .
H8A H 0.5586 1.0001 0.3915 0.025 Uiso 1 1 calc R U . . .
C9A C 0.74552(14) 1.02655(12) 0.46393(9) 0.0264(3) Uani 1 1 d . . . . .
H9A1 H 0.7403 1.1212 0.4629 0.032 Uiso 1 1 calc R U . . .
H9A2 H 0.7633 0.9993 0.5282 0.032 Uiso 1 1 calc R U . . .
C10A C 0.89371(13) 0.98024(11) 0.37935(8) 0.0228(2) Uani 1 1 d . . . . .
C11A C 0.99111(15) 0.87434(12) 0.39107(9) 0.0286(3) Uani 1 1 d . . . . .
H11A H 0.9657 0.8316 0.4537 0.034 Uiso 1 1 calc R U . . .
C12A C 1.12489(15) 0.83026(12) 0.31254(10) 0.0319(3) Uani 1 1 d . . . . .
H12A H 1.1901 0.7576 0.3216 0.038 Uiso 1 1 calc R U . . .
C13A C 1.16319(15) 0.89194(13) 0.22126(9) 0.0313(3) Uani 1 1 d . . . . .
H13A H 1.2546 0.8618 0.1674 0.038 Uiso 1 1 calc R U . . .
C14A C 1.06779(16) 0.99801(13) 0.20844(9) 0.0326(3) Uani 1 1 d . . . . .
H14A H 1.0942 1.0410 0.1459 0.039 Uiso 1 1 calc R U . . .
C15A C 0.93372(15) 1.04128(12) 0.28705(9) 0.0283(3) Uani 1 1 d . . . . .
H15A H 0.8683 1.1137 0.2777 0.034 Uiso 1 1 calc R U . . .
O1A O 0.60334(11) 0.77708(8) 0.53801(6) 0.0312(2) Uani 1 1 d . . . . .
C1B C 0.16555(15) 0.74882(11) 0.90864(8) 0.0252(3) Uani 1 1 d . . . . .
C2B C 0.17865(18) 0.86630(13) 0.95158(10) 0.0352(3) Uani 1 1 d . . . . .
H2B H 0.0906 0.8957 1.0076 0.042 Uiso 1 1 calc R U . . .
C3B C 0.3201(2) 0.94043(14) 0.91273(12) 0.0467(4) Uani 1 1 d . . . . .
H3B H 0.3301 1.0199 0.9427 0.056 Uiso 1 1 calc R U . . .
C4B C 0.44706(19) 0.89826(15) 0.82983(12) 0.0456(4) Uani 1 1 d . . . . .
H4B H 0.5443 0.9488 0.8034 0.055 Uiso 1 1 calc R U . . .
C5B C 0.43276(16) 0.78321(13) 0.78561(10) 0.0363(3) Uani 1 1 d . . . . .
H5B H 0.5186 0.7561 0.7278 0.044 Uiso 1 1 calc R U . . .
C6B C 0.29355(15) 0.70718(12) 0.82534(9) 0.0284(3) Uani 1 1 d . . . . .
H6B H 0.2854 0.6270 0.7959 0.034 Uiso 1 1 calc R U . . .
C7B C 0.01000(15) 0.67299(12) 0.95243(8) 0.0254(3) Uani 1 1 d . . . . .
C8B C 0.01825(14) 0.52712(11) 0.94629(8) 0.0246(3) Uani 1 1 d . . . . .
H8B H 0.1346 0.4992 0.9064 0.029 Uiso 1 1 calc R U . . .
C9B C -0.11129(16) 0.48155(13) 0.89383(9) 0.0312(3) Uani 1 1 d . . . . .
H9B1 H -0.1149 0.3870 0.8959 0.037 Uiso 1 1 calc R U . . .
H9B2 H -0.2255 0.5152 0.9298 0.037 Uiso 1 1 calc R U . . .
C10B C -0.06493(15) 0.52646(12) 0.78632(9) 0.0265(3) Uani 1 1 d . . . . .
C11B C -0.13683(15) 0.63724(12) 0.75844(9) 0.0294(3) Uani 1 1 d . . . . .
H11B H -0.2194 0.6849 0.8073 0.035 Uiso 1 1 calc R U . . .
C12B C -0.08879(16) 0.67856(12) 0.65984(9) 0.0308(3) Uani 1 1 d . . . . .
H12B H -0.1394 0.7537 0.6414 0.037 Uiso 1 1 calc R U . . .
C13B C 0.03257(16) 0.61053(13) 0.58854(9) 0.0311(3) Uani 1 1 d . . . . .
H13B H 0.0658 0.6391 0.5212 0.037 Uiso 1 1 calc R U . . .
C14B C 0.10557(16) 0.50073(13) 0.61542(9) 0.0320(3) Uani 1 1 d . . . . .
H14B H 0.1892 0.4540 0.5665 0.038 Uiso 1 1 calc R U . . .
C15B C 0.05674(16) 0.45890(12) 0.71357(9) 0.0302(3) Uani 1 1 d . . . . .
H15B H 0.1069 0.3832 0.7315 0.036 Uiso 1 1 calc R U . . .
O1B O -0.12353(11) 0.72683(9) 0.99535(7) 0.0377(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A C2A 1.3942(16) . ?
C1A C6A 1.3951(16) . ?
C1A C7A 1.4932(15) . ?
C2A C3A 1.3916(17) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.3852(19) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.385(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.3849(18) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A O1A 1.2191(14) . ?
C7A C8A 1.5291(15) . ?
C8A C9A 1.5424(15) . ?
C8A C8A 1.551(2) 2_676 ?
C8A H8A 1.0000 . ?
C9A C10A 1.5102(15) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10A C15A 1.3898(16) . ?
C10A C11A 1.3903(16) . ?
C11A C12A 1.3880(17) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.3810(18) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.3863(18) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.3871(17) . ?
C14A H14A 0.9500 . ?
C15A H15A 0.9500 . ?
C1B C2B 1.3922(18) . ?
C1B C6B 1.3941(16) . ?
C1B C7B 1.4929(17) . ?
C2B C3B 1.385(2) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.388(2) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.380(2) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3856(18) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B O1B 1.2203(14) . ?
C7B C8B 1.5275(16) . ?
C8B C9B 1.5443(17) . ?
C8B C8B 1.550(2) 2_567 ?
C8B H8B 1.0000 . ?
C9B C10B 1.5140(16) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
C10B C15B 1.3918(17) . ?
C10B C11B 1.3932(17) . ?
C11B C12B 1.3884(17) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.3824(18) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.3838(18) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.3844(17) . ?
C14B H14B 0.9500 . ?
C15B H15B 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
C2A C1A C6A 119.60(11) . . ?
C2A C1A C7A 122.37(10) . . ?
C6A C1A C7A 118.02(10) . . ?
C3A C2A C1A 119.86(11) . . ?
C3A C2A H2A 120.1 . . ?
C1A C2A H2A 120.1 . . ?
C4A C3A C2A 119.91(12) . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C5A C4A C3A 120.49(12) . . ?
C5A C4A H4A 119.8 . . ?
C3A C4A H4A 119.8 . . ?
C4A C5A C6A 119.82(12) . . ?
C4A C5A H5A 120.1 . . ?
C6A C5A H5A 120.1 . . ?
C5A C6A C1A 120.27(11) . . ?
C5A C6A H6A 119.9 . . ?
C1A C6A H6A 119.9 . . ?
O1A C7A C1A 120.21(10) . . ?
O1A C7A C8A 119.80(10) . . ?
C1A C7A C8A 119.97(9) . . ?
C7A C8A C9A 109.47(9) . . ?
C7A C8A C8A 107.88(11) . 2_676 ?
C9A C8A C8A 111.56(11) . 2_676 ?
C7A C8A H8A 109.3 . . ?
C9A C8A H8A 109.3 . . ?
C8A C8A H8A 109.3 2_676 . ?
C10A C9A C8A 112.27(9) . . ?
C10A C9A H9A1 109.2 . . ?
C8A C9A H9A1 109.2 . . ?
C10A C9A H9A2 109.2 . . ?
C8A C9A H9A2 109.2 . . ?
H9A1 C9A H9A2 107.9 . . ?
C15A C10A C11A 118.40(10) . . ?
C15A C10A C9A 120.55(10) . . ?
C11A C10A C9A 121.03(11) . . ?
C12A C11A C10A 120.91(11) . . ?
C12A C11A H11A 119.5 . . ?
C10A C11A H11A 119.5 . . ?
C13A C12A C11A 120.03(11) . . ?
C13A C12A H12A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C12A C13A C14A 119.79(11) . . ?
C12A C13A H13A 120.1 . . ?
C14A C13A H13A 120.1 . . ?
C13A C14A C15A 119.93(12) . . ?
C13A C14A H14A 120.0 . . ?
C15A C14A H14A 120.0 . . ?
C14A C15A C10A 120.93(11) . . ?
C14A C15A H15A 119.5 . . ?
C10A C15A H15A 119.5 . . ?
C2B C1B C6B 119.81(12) . . ?
C2B C1B C7B 118.10(11) . . ?
C6B C1B C7B 122.07(11) . . ?
C3B C2B C1B 120.04(13) . . ?
C3B C2B H2B 120.0 . . ?
C1B C2B H2B 120.0 . . ?
C2B C3B C4B 119.81(14) . . ?
C2B C3B H3B 120.1 . . ?
C4B C3B H3B 120.1 . . ?
C5B C4B C3B 120.34(13) . . ?
C5B C4B H4B 119.8 . . ?
C3B C4B H4B 119.8 . . ?
C4B C5B C6B 120.20(13) . . ?
C4B C5B H5B 119.9 . . ?
C6B C5B H5B 119.9 . . ?
C5B C6B C1B 119.77(12) . . ?
C5B C6B H6B 120.1 . . ?
C1B C6B H6B 120.1 . . ?
O1B C7B C1B 120.30(11) . . ?
O1B C7B C8B 119.56(11) . . ?
C1B C7B C8B 120.12(10) . . ?
C7B C8B C9B 109.14(10) . . ?
C7B C8B C8B 108.21(11) . 2_567 ?
C9B C8B C8B 112.02(12) . 2_567 ?
C7B C8B H8B 109.1 . . ?
C9B C8B H8B 109.1 . . ?
C8B C8B H8B 109.1 2_567 . ?
C10B C9B C8B 111.13(10) . . ?
C10B C9B H9B1 109.4 . . ?
C8B C9B H9B1 109.4 . . ?
C10B C9B H9B2 109.4 . . ?
C8B C9B H9B2 109.4 . . ?
H9B1 C9B H9B2 108.0 . . ?
C15B C10B C11B 118.67(11) . . ?
C15B C10B C9B 119.76(11) . . ?
C11B C10B C9B 121.53(11) . . ?
C12B C11B C10B 120.52(11) . . ?
C12B C11B H11B 119.7 . . ?
C10B C11B H11B 119.7 . . ?
C13B C12B C11B 120.08(11) . . ?
C13B C12B H12B 120.0 . . ?
C11B C12B H12B 120.0 . . ?
C12B C13B C14B 119.93(11) . . ?
C12B C13B H13B 120.0 . . ?
C14B C13B H13B 120.0 . . ?
C13B C14B C15B 120.01(12) . . ?
C13B C14B H14B 120.0 . . ?
C15B C14B H14B 120.0 . . ?
C14B C15B C10B 120.78(11) . . ?
C14B C15B H15B 119.6 . . ?
C10B C15B H15B 119.6 . . ?

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_cu_jpu_519_2_1_jahn
_database_code_depnum_ccdc_archive 'CCDC 1538564'
_audit_update_record             
;
2017-03-16 deposited with the CCDC.
2017-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 F2 O2'
_chemical_formula_sum            'C30 H24 F2 O2'
_chemical_formula_weight         454.49
_chemical_compound_source        'synthesized by the authors'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.2454(2)
_cell_length_b                   10.3667(3)
_cell_length_c                   14.2973(4)
_cell_angle_alpha                90.2010(10)
_cell_angle_beta                 104.5580(10)
_cell_angle_gamma                90.5850(10)
_cell_volume                     1182.78(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9940
_cell_measurement_theta_min      4.2650
_cell_measurement_theta_max      72.1967

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.356
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.212
_exptl_absorpt_coefficient_mu    0.730
_shelx_estimated_absorpt_T_min   0.781
_shelx_estimated_absorpt_T_max   0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'

_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20215
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.265
_diffrn_reflns_theta_max         72.189
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4622
_reflns_number_gt                4131
_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       'Bruker Instrument Service v4.2.9'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0405P)²+0.3850P] 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         4622
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
C1A C -0.07079(15) 0.74967(11) 0.09658(8) 0.0242(2) Uani 1 1 d . . . . .
C2A C -0.13035(18) 0.86880(12) 0.05866(9) 0.0345(3) Uani 1 1 d . . . . .
H2A H -0.1031 0.8998 0.0020 0.041 Uiso 1 1 calc R U . . .
C3A C -0.2290(2) 0.94218(14) 0.10322(11) 0.0453(4) Uani 1 1 d . . . . .
H3A H -0.2720 1.0222 0.0762 0.054 Uiso 1 1 calc R U . . .
C4A C -0.26472(18) 0.89820(14) 0.18766(11) 0.0423(3) Uani 1 1 d . . . . .
H4A H -0.3320 0.9486 0.2185 0.051 Uiso 1 1 calc R U . . .
C5A C -0.20324(16) 0.78191(13) 0.22692(10) 0.0340(3) Uani 1 1 d . . . . .
H5A H -0.2259 0.7535 0.2855 0.041 Uiso 1 1 calc R U . . .
C6A C -0.10815(15) 0.70624(11) 0.18093(8) 0.0266(2) Uani 1 1 d . . . . .
H6A H -0.0686 0.6249 0.2070 0.032 Uiso 1 1 calc R U . . .
C7A C 0.03605(15) 0.67443(11) 0.04654(8) 0.0261(2) Uani 1 1 d . . . . .
C8A C 0.03704(15) 0.52691(11) 0.05162(8) 0.0253(3) Uani 1 1 d . . . . .
H8A H -0.0350 0.4980 0.0945 0.030 Uiso 1 1 calc R U . . .
C9A C 0.21826(16) 0.48152(13) 0.09445(9) 0.0326(3) Uani 1 1 d . . . . .
H9A1 H 0.2220 0.3863 0.0902 0.039 Uiso 1 1 calc R U . . .
H9A2 H 0.2925 0.5180 0.0563 0.039 Uiso 1 1 calc R U . . .
C10A C 0.28056(15) 0.52353(11) 0.19876(9) 0.0274(3) Uani 1 1 d . . . . .
C11A C 0.37861(16) 0.63404(12) 0.22467(9) 0.0300(3) Uani 1 1 d . . . . .
H11A H 0.4123 0.6823 0.1763 0.036 Uiso 1 1 calc R U . . .
C12A C 0.42827(15) 0.67502(12) 0.32069(9) 0.0308(3) Uani 1 1 d . . . . .
H12A H 0.4956 0.7504 0.3384 0.037 Uiso 1 1 calc R U . . .
C13A C 0.37737(15) 0.60353(12) 0.38876(9) 0.0297(3) Uani 1 1 d . . . . .
C14A C 0.28135(16) 0.49321(12) 0.36682(9) 0.0318(3) Uani 1 1 d . . . . .
H14A H 0.2487 0.4453 0.4158 0.038 Uiso 1 1 calc R U . . .
C15A C 0.23357(16) 0.45406(12) 0.27081(9) 0.0305(3) Uani 1 1 d . . . . .
H15A H 0.1672 0.3780 0.2540 0.037 Uiso 1 1 calc R U . . .
F1A F 0.42442(10) 0.64314(8) 0.48266(5) 0.0432(2) Uani 1 1 d . . . . .
F1B F 0.56271(11) 0.85270(9) 0.85561(6) 0.0465(2) Uani 1 1 d . . . . .
O1A O 0.12030(13) 0.72955(9) -0.00024(7) 0.0397(2) Uani 1 1 d . . . . .
C1B C 1.05902(14) 0.74832(10) 0.61228(8) 0.0224(2) Uani 1 1 d . . . . .
C2B C 1.11428(16) 0.63041(11) 0.58536(10) 0.0300(3) Uani 1 1 d . . . . .
H2B H 1.0827 0.6034 0.5196 0.036 Uiso 1 1 calc R U . . .
C3B C 1.21498(17) 0.55274(12) 0.65410(11) 0.0377(3) Uani 1 1 d . . . . .
H3B H 1.2548 0.4736 0.6353 0.045 Uiso 1 1 calc R U . . .
C4B C 1.25782(16) 0.59002(12) 0.75007(11) 0.0362(3) Uani 1 1 d . . . . .
H4B H 1.3267 0.5362 0.7970 0.043 Uiso 1 1 calc R U . . .
C5B C 1.20078(16) 0.70582(12) 0.77833(9) 0.0319(3) Uani 1 1 d . . . . .
H5B H 1.2281 0.7300 0.8446 0.038 Uiso 1 1 calc R U . . .
C6B C 1.10371(15) 0.78612(11) 0.70938(8) 0.0257(2) Uani 1 1 d . . . . .
H6B H 1.0677 0.8667 0.7282 0.031 Uiso 1 1 calc R U . . .
C7B C 0.95083(14) 0.82895(10) 0.53591(8) 0.0228(2) Uani 1 1 d . . . . .
C8B C 0.96606(14) 0.97593(10) 0.54287(8) 0.0215(2) Uani 1 1 d . . . . .
H8B H 1.0474 1.0006 0.6050 0.026 Uiso 1 1 calc R U . . .
C9B C 0.79342(15) 1.03374(11) 0.54082(9) 0.0269(3) Uani 1 1 d . . . . .
H9B1 H 0.8032 1.1290 0.5433 0.032 Uiso 1 1 calc R U . . .
H9B2 H 0.7128 1.0093 0.4793 0.032 Uiso 1 1 calc R U . . .
C10B C 0.72711(14) 0.98750(11) 0.62438(8) 0.0237(2) Uani 1 1 d . . . . .
C11B C 0.61493(15) 0.88408(12) 0.61327(9) 0.0280(3) Uani 1 1 d . . . . .
H11B H 0.5761 0.8444 0.5516 0.034 Uiso 1 1 calc R U . . .
C12B C 0.55854(16) 0.83770(12) 0.69065(10) 0.0317(3) Uani 1 1 d . . . . .
H12B H 0.4822 0.7669 0.6828 0.038 Uiso 1 1 calc R U . . .
C13B C 0.61642(15) 0.89730(12) 0.77881(9) 0.0303(3) Uani 1 1 d . . . . .
C14B C 0.72611(16) 1.00050(13) 0.79343(9) 0.0313(3) Uani 1 1 d . . . . .
H14B H 0.7629 1.0403 0.8552 0.038 Uiso 1 1 calc R U . . .
C15B C 0.78142(15) 1.04479(11) 0.71522(9) 0.0279(3) Uani 1 1 d . . . . .
H15B H 0.8579 1.1156 0.7238 0.033 Uiso 1 1 calc R U . . .
O1B O 0.85387(11) 0.77840(8) 0.46653(6) 0.0320(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A C6A 1.3927(16) . ?
C1A C2A 1.3941(17) . ?
C1A C7A 1.4911(16) . ?
C2A C3A 1.384(2) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.390(2) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.378(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.3895(17) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A O1A 1.2184(15) . ?
C7A C8A 1.5313(16) . ?
C8A C9A 1.5445(17) . ?
C8A C8A 1.548(2) 2_565 ?
C8A H8A 1.0000 . ?
C9A C10A 1.5111(16) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10A C15A 1.3893(18) . ?
C10A C11A 1.3895(17) . ?
C11A C12A 1.3938(18) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.3699(18) . ?
C12A H12A 0.9500 . ?
C13A F1A 1.3611(13) . ?
C13A C14A 1.3737(18) . ?
C14A C15A 1.3875(18) . ?
C14A H14A 0.9500 . ?
C15A H15A 0.9500 . ?
F1B C13B 1.3636(14) . ?
C1B C2B 1.3951(16) . ?
C1B C6B 1.3974(16) . ?
C1B C7B 1.4895(16) . ?
C2B C3B 1.3830(19) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.381(2) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.3890(19) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3885(17) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B O1B 1.2193(14) . ?
C7B C8B 1.5285(15) . ?
C8B C9B 1.5437(15) . ?
C8B C8B 1.552(2) 2_776 ?
C8B H8B 1.0000 . ?
C9B C10B 1.5109(16) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
C10B C11B 1.3910(17) . ?
C10B C15B 1.3917(16) . ?
C11B C12B 1.3889(18) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.3727(19) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.3748(18) . ?
C14B C15B 1.3874(17) . ?
C14B H14B 0.9500 . ?
C15B H15B 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
C6A C1A C2A 119.50(11) . . ?
C6A C1A C7A 122.04(11) . . ?
C2A C1A C7A 118.43(11) . . ?
C3A C2A C1A 120.32(13) . . ?
C3A C2A H2A 119.8 . . ?
C1A C2A H2A 119.8 . . ?
C2A C3A C4A 119.67(13) . . ?
C2A C3A H3A 120.2 . . ?
C4A C3A H3A 120.2 . . ?
C5A C4A C3A 120.43(12) . . ?
C5A C4A H4A 119.8 . . ?
C3A C4A H4A 119.8 . . ?
C4A C5A C6A 120.07(13) . . ?
C4A C5A H5A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C5A C6A C1A 119.96(12) . . ?
C5A C6A H6A 120.0 . . ?
C1A C6A H6A 120.0 . . ?
O1A C7A C1A 120.34(11) . . ?
O1A C7A C8A 119.58(11) . . ?
C1A C7A C8A 120.06(10) . . ?
C7A C8A C9A 109.12(10) . . ?
C7A C8A C8A 108.14(11) . 2_565 ?
C9A C8A C8A 112.14(12) . 2_565 ?
C7A C8A H8A 109.1 . . ?
C9A C8A H8A 109.1 . . ?
C8A C8A H8A 109.1 2_565 . ?
C10A C9A C8A 110.94(10) . . ?
C10A C9A H9A1 109.5 . . ?
C8A C9A H9A1 109.5 . . ?
C10A C9A H9A2 109.5 . . ?
C8A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 108.0 . . ?
C15A C10A C11A 118.55(11) . . ?
C15A C10A C9A 119.80(11) . . ?
C11A C10A C9A 121.58(12) . . ?
C10A C11A C12A 120.91(12) . . ?
C10A C11A H11A 119.5 . . ?
C12A C11A H11A 119.5 . . ?
C13A C12A C11A 118.16(11) . . ?
C13A C12A H12A 120.9 . . ?
C11A C12A H12A 120.9 . . ?
F1A C13A C12A 118.61(11) . . ?
F1A C13A C14A 118.30(12) . . ?
C12A C13A C14A 123.09(11) . . ?
C13A C14A C15A 117.79(12) . . ?
C13A C14A H14A 121.1 . . ?
C15A C14A H14A 121.1 . . ?
C14A C15A C10A 121.50(11) . . ?
C14A C15A H15A 119.2 . . ?
C10A C15A H15A 119.2 . . ?
C2B C1B C6B 119.49(11) . . ?
C2B C1B C7B 118.38(10) . . ?
C6B C1B C7B 122.13(10) . . ?
C3B C2B C1B 120.15(12) . . ?
C3B C2B H2B 119.9 . . ?
C1B C2B H2B 119.9 . . ?
C4B C3B C2B 120.15(12) . . ?
C4B C3B H3B 119.9 . . ?
C2B C3B H3B 119.9 . . ?
C3B C4B C5B 120.37(12) . . ?
C3B C4B H4B 119.8 . . ?
C5B C4B H4B 119.8 . . ?
C6B C5B C4B 119.82(12) . . ?
C6B C5B H5B 120.1 . . ?
C4B C5B H5B 120.1 . . ?
C5B C6B C1B 119.97(11) . . ?
C5B C6B H6B 120.0 . . ?
C1B C6B H6B 120.0 . . ?
O1B C7B C1B 120.42(10) . . ?
O1B C7B C8B 119.85(10) . . ?
C1B C7B C8B 119.70(10) . . ?
C7B C8B C9B 109.55(9) . . ?
C7B C8B C8B 107.93(11) . 2_776 ?
C9B C8B C8B 111.81(11) . 2_776 ?
C7B C8B H8B 109.2 . . ?
C9B C8B H8B 109.2 . . ?
C8B C8B H8B 109.2 2_776 . ?
C10B C9B C8B 111.99(9) . . ?
C10B C9B H9B1 109.2 . . ?
C8B C9B H9B1 109.2 . . ?
C10B C9B H9B2 109.2 . . ?
C8B C9B H9B2 109.2 . . ?
H9B1 C9B H9B2 107.9 . . ?
C11B C10B C15B 118.43(11) . . ?
C11B C10B C9B 120.91(11) . . ?
C15B C10B C9B 120.63(11) . . ?
C12B C11B C10B 121.27(11) . . ?
C12B C11B H11B 119.4 . . ?
C10B C11B H11B 119.4 . . ?
C13B C12B C11B 118.00(11) . . ?
C13B C12B H12B 121.0 . . ?
C11B C12B H12B 121.0 . . ?
F1B C13B C12B 118.75(11) . . ?
F1B C13B C14B 118.23(12) . . ?
C12B C13B C14B 123.02(11) . . ?
C13B C14B C15B 117.98(12) . . ?
C13B C14B H14B 121.0 . . ?
C15B C14B H14B 121.0 . . ?
C14B C15B C10B 121.30(11) . . ?
C14B C15B H15B 119.4 . . ?
C10B C15B H15B 119.4 . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_cu_jpu_463_2_jahn_5
_database_code_depnum_ccdc_archive 'CCDC 1484494'
_audit_update_record             
;
2017-11-21 deposited with the CCDC.
2017-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 Cl2 O2'
_chemical_formula_sum            'C30 H24 Cl2 O2'
_chemical_formula_weight         487.39
_chemical_compound_source        'synthesized by the authors'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.1640(3)
_cell_length_b                   8.8470(4)
_cell_length_c                   12.0067(5)
_cell_angle_alpha                106.1310(10)
_cell_angle_beta                 92.9630(10)
_cell_angle_gamma                101.4670(10)
_cell_volume                     612.44(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      3.8574
_cell_measurement_theta_max      72.0562

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             254
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.580
_shelx_estimated_absorpt_T_min   0.698
_shelx_estimated_absorpt_T_max   0.747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6951
_exptl_absorpt_correction_T_max  0.7540
_exptl_absorpt_process_details   
'TWINABS - Bruker AXS scaling for twinned crystals-Version 2012/1'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            2394
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.857
_diffrn_reflns_theta_max         72.175
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2394
_reflns_number_gt                2327
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.

The crystal was refined as non-merohedral twin
;

_computing_data_collection       'Bruker Instrument Service v4.2.9'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0373P)²+0.1466P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2394
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0783
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
Cl1 Cl 1.08732(7) 1.02933(5) 0.16445(3) 0.04484(13) Uani 1 1 d . . . . .
O1 O 0.77739(17) 0.36704(13) 0.38343(9) 0.0368(2) Uani 1 1 d . . . . .
C1 C 0.5380(2) 0.39133(16) 0.23321(11) 0.0269(3) Uani 1 1 d . . . . .
C2 C 0.6464(3) 0.3021(2) 0.14766(14) 0.0411(4) Uani 1 1 d . . . . .
H2 H 0.776696 0.270254 0.169640 0.049 Uiso 1 1 calc R U . . .
C3 C 0.5646(4) 0.2599(2) 0.03108(15) 0.0562(5) Uani 1 1 d . . . . .
H3 H 0.638907 0.199352 -0.026726 0.067 Uiso 1 1 calc R U . . .
C4 C 0.3755(4) 0.3055(2) -0.00148(14) 0.0557(5) Uani 1 1 d . . . . .
H4 H 0.320637 0.277166 -0.081663 0.067 Uiso 1 1 calc R U . . .
C5 C 0.2662(3) 0.3919(2) 0.08185(14) 0.0473(4) Uani 1 1 d . . . . .
H5 H 0.135313 0.422299 0.059145 0.057 Uiso 1 1 calc R U . . .
C6 C 0.3462(3) 0.43470(19) 0.19873(12) 0.0343(3) Uani 1 1 d . . . . .
H6 H 0.269534 0.494179 0.255849 0.041 Uiso 1 1 calc R U . . .
C7 C 0.6295(2) 0.42836(15) 0.35769(11) 0.0249(3) Uani 1 1 d . . . . .
C8 C 0.5417(2) 0.54378(15) 0.45533(10) 0.0219(3) Uani 1 1 d . . . . .
H8 H 0.414849 0.578189 0.421449 0.026 Uiso 1 1 calc R U . . .
C9 C 0.7307(2) 0.69373(16) 0.51249(11) 0.0274(3) Uani 1 1 d . . . . .
H9A H 0.673940 0.769645 0.575197 0.033 Uiso 1 1 calc R U . . .
H9B H 0.853552 0.660018 0.548784 0.033 Uiso 1 1 calc R U . . .
C10 C 0.8207(2) 0.77968(15) 0.42688(11) 0.0251(3) Uani 1 1 d . . . . .
C11 C 1.0132(2) 0.75277(19) 0.37736(14) 0.0358(3) Uani 1 1 d . . . . .
H11 H 1.090904 0.681329 0.399718 0.043 Uiso 1 1 calc R U . . .
C12 C 1.0948(2) 0.8275(2) 0.29613(14) 0.0370(3) Uani 1 1 d . . . . .
H12 H 1.225361 0.806097 0.262056 0.044 Uiso 1 1 calc R U . . .
C13 C 0.9839(2) 0.93340(17) 0.26540(12) 0.0302(3) Uani 1 1 d . . . . .
C14 C 0.7931(3) 0.96435(17) 0.31323(13) 0.0352(3) Uani 1 1 d . . . . .
H14 H 0.718007 1.037821 0.291889 0.042 Uiso 1 1 calc R U . . .
C15 C 0.7127(2) 0.88628(17) 0.39310(12) 0.0311(3) Uani 1 1 d . . . . .
H15 H 0.580247 0.906236 0.425609 0.037 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
Cl1 C13 1.7414(14) . ?
O1 C7 1.2174(16) . ?
C1 C6 1.391(2) . ?
C1 C2 1.399(2) . ?
C1 C7 1.4920(18) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.5264(17) . ?
C8 C8 1.541(2) 2_666 ?
C8 C9 1.5444(18) . ?
C8 H8 1.0000 . ?
C9 C10 1.5059(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.387(2) . ?
C10 C15 1.3896(19) . ?
C11 C12 1.385(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(2) . ?
C14 C15 1.387(2) . ?
C14 H14 0.9500 . ?
C15 H15 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
C6 C1 C2 118.71(14) . . ?
C6 C1 C7 123.46(12) . . ?
C2 C1 C7 117.77(13) . . ?
C3 C2 C1 120.19(17) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.23(17) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.11(16) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.25(18) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.50(15) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 C7 C1 120.34(12) . . ?
O1 C7 C8 118.48(12) . . ?
C1 C7 C8 121.19(11) . . ?
C7 C8 C8 109.23(12) . 2_666 ?
C7 C8 C9 108.72(10) . . ?
C8 C8 C9 111.42(12) 2_666 . ?
C7 C8 H8 109.1 . . ?
C8 C8 H8 109.1 2_666 . ?
C9 C8 H8 109.1 . . ?
C10 C9 C8 112.85(10) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C15 117.61(12) . . ?
C11 C10 C9 120.90(12) . . ?
C15 C10 C9 121.49(12) . . ?
C12 C11 C10 121.62(13) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C13 C12 C11 119.07(14) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C12 121.09(13) . . ?
C14 C13 Cl1 119.62(11) . . ?
C12 C13 Cl1 119.29(11) . . ?
C13 C14 C15 118.79(13) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C14 C15 C10 121.81(13) . . ?
C14 C15 H15 119.1 . . ?
C10 C15 H15 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.7(2) . . . . ?
C7 C1 C2 C3 177.95(15) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C7 C1 C6 C5 -177.84(14) . . . . ?
C6 C1 C7 O1 168.98(13) . . . . ?
C2 C1 C7 O1 -8.10(19) . . . . ?
C6 C1 C7 C8 -11.31(19) . . . . ?
C2 C1 C7 C8 171.61(12) . . . . ?
O1 C7 C8 C8 -56.98(18) . . . 2_666 ?
C1 C7 C8 C8 123.31(14) . . . 2_666 ?
O1 C7 C8 C9 64.80(15) . . . . ?
C1 C7 C8 C9 -114.91(12) . . . . ?
C7 C8 C9 C10 57.95(14) . . . . ?
C8 C8 C9 C10 178.39(13) 2_666 . . . ?
C8 C9 C10 C11 -97.86(15) . . . . ?
C8 C9 C10 C15 81.03(16) . . . . ?
C15 C10 C11 C12 -0.7(2) . . . . ?
C9 C10 C11 C12 178.23(14) . . . . ?
C10 C11 C12 C13 1.2(2) . . . . ?
C11 C12 C13 C14 -0.7(2) . . . . ?
C11 C12 C13 Cl1 179.34(12) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
Cl1 C13 C14 C15 179.72(11) . . . . ?
C13 C14 C15 C10 0.8(2) . . . . ?
C11 C10 C15 C14 -0.3(2) . . . . ?
C9 C10 C15 C14 -179.19(13) . . . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.040

