# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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 
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data_cr111_2
_database_code_depnum_ccdc_archive 'CCDC 1537591'
_audit_update_record             
;
2017-03-13 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C45 H36 O6, C H2 Cl2'
_chemical_formula_sum            'C46 H38 Cl2 O6'
_chemical_formula_weight         757.66

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.6304(4)
_cell_length_b                   10.6493(5)
_cell_length_c                   16.3294(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.655(5)
_cell_angle_gamma                90
_cell_volume                     1788.45(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    11663
_cell_measurement_theta_min      4.2480
_cell_measurement_theta_max      66.9250

_exptl_crystal_description       rhombohedral
_exptl_crystal_colour            'clear intense colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33785
_exptl_crystal_size_mid          0.2757
_exptl_crystal_size_min          0.08735
_exptl_absorpt_coefficient_mu    2.065
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.322
_exptl_absorpt_correction_T_max  0.707
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_reflns_number            25119
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.299
_diffrn_reflns_theta_max         66.893
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.9928
_diffrn_measured_fraction_theta_full 0.9932
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             6318
_reflns_number_gt                5850
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.974

_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       'Gemini, (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXLe  (Sheldrick, 2011)'
_computing_publication_material  'SHELXLe  (Sheldrick, 2011)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0875P)²+0.2755P] 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     SHELXL
_refine_ls_extinction_coef       0.0033(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2497 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.010(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6318
_refine_ls_number_parameters     488
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1224
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_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 0.76199(10) 0.79887(11) 0.86766(8) 0.0286(3) Uani 1 1 d . . . . .
O1 O 0.8398(3) 0.8024(3) 1.57051(18) 0.0178(6) Uani 1 1 d . . . . .
Cl2 Cl 1.03482(11) 0.86636(13) 0.93409(7) 0.0316(3) Uani 1 1 d . . . . .
O2 O 0.2890(3) 0.6264(3) 1.16899(19) 0.0149(6) Uani 1 1 d . . . . .
O3 O 0.3498(3) 0.7169(3) 1.05014(18) 0.0149(6) Uani 1 1 d . . . . .
O4 O 0.6152(3) 0.7479(3) 1.5457(2) 0.0198(7) Uani 1 1 d . . . . .
O5 O 1.0570(3) 0.8827(3) 1.1408(2) 0.0196(7) Uani 1 1 d . . . . .
C46 C 0.2586(4) 0.6476(4) 1.0806(3) 0.0155(9) Uani 1 1 d . . . . .
H46A H 0.2472 0.5667 1.0524 0.019 Uiso 1 1 calc R U . . .
H46B H 0.1758 0.6910 1.0644 0.019 Uiso 1 1 calc R U . . .
C45 C 0.6396(4) 1.1296(4) 1.3765(3) 0.0148(9) Uani 1 1 d . . . . .
H45A H 0.6866 1.1648 1.4304 0.018 Uiso 1 1 calc R U . . .
H45B H 0.5771 1.1920 1.3484 0.018 Uiso 1 1 calc R U . . .
C44 C 0.4433(4) 0.9819(4) 1.3426(3) 0.0152(9) Uani 1 1 d . . . . .
C43 C 0.7349(4) 0.7692(5) 1.6051(3) 0.0204(9) Uani 1 1 d . . . . .
H43A H 0.7586 0.6938 1.6388 0.024 Uiso 1 1 calc R U . . .
H43B H 0.7230 0.8357 1.6430 0.024 Uiso 1 1 calc R U . . .
C42 C 0.3763(4) 1.0520(4) 1.2633(3) 0.0146(9) Uani 1 1 d . . . . .
H42A H 0.3990 1.1403 1.2704 0.018 Uiso 1 1 calc R U . . .
H42B H 0.2830 1.0450 1.2549 0.018 Uiso 1 1 calc R U . . .
C41 C 1.0987(5) 1.3630(5) 1.1559(3) 0.0254(10) Uani 1 1 d . . . . .
H41A H 1.1176 1.4478 1.1772 0.030 Uiso 1 1 calc R U . . .
H41B H 1.0761 1.3135 1.1999 0.030 Uiso 1 1 calc R U . . .
C40 C 1.0194(4) 0.6981(4) 1.4235(3) 0.0150(9) Uani 1 1 d . . . . .
H40 H 1.0920 0.7251 1.4063 0.018 Uiso 1 1 calc R U . . .
C39 C 0.9953(4) 0.5309(4) 1.3133(3) 0.0140(9) Uani 1 1 d . . . . .
H39A H 1.0894 0.5279 1.3255 0.017 Uiso 1 1 calc R U . . .
H39B H 0.9624 0.4457 1.3045 0.017 Uiso 1 1 calc R U . . .
C38 C 0.7355(4) 0.4747(4) 1.1861(3) 0.0140(9) Uani 1 1 d . . . . .
H38A H 0.7910 0.4096 1.2177 0.017 Uiso 1 1 calc R U . . .
H38B H 0.6978 0.4423 1.1297 0.017 Uiso 1 1 calc R U . . .
C37 C 1.0160(4) 0.7094(4) 1.2193(3) 0.0139(8) Uani 1 1 d . . . . .
H37 H 1.0988 0.7215 1.2544 0.017 Uiso 1 1 calc R U . . .
C36 C 0.6241(4) 0.9412(4) 1.4640(3) 0.0164(9) Uani 1 1 d . . . . .
H36 H 0.7045 0.9645 1.4984 0.020 Uiso 1 1 calc R U . . .
C35 C 0.7357(4) 1.1069(4) 1.3230(3) 0.0124(8) Uani 1 1 d . . . . .
C34 C 1.0142(4) 1.0065(4) 1.1232(3) 0.0151(8) Uani 1 1 d . . . . .
H34A H 0.9227 1.0063 1.0939 0.018 Uiso 1 1 calc R U . . .
H34B H 1.0617 1.0450 1.0863 0.018 Uiso 1 1 calc R U . . .
C33 C 0.9544(4) 1.0426(4) 1.3206(3) 0.0172(9) Uani 1 1 d . . . . .
H33 H 1.0339 1.0070 1.3477 0.021 Uiso 1 1 calc R U . . .
C32 C 0.5283(4) 1.0092(4) 1.0762(3) 0.0152(9) Uani 1 1 d . . . . .
H32 H 0.5833 1.0510 1.0492 0.018 Uiso 1 1 calc R U . . .
C31 C 0.5299(4) 0.5035(4) 1.3468(3) 0.0147(8) Uani 1 1 d . . . . .
H31 H 0.5355 0.4874 1.4035 0.018 Uiso 1 1 calc R U . . .
C30 C 0.4763(4) 0.8956(4) 1.0446(3) 0.0156(9) Uani 1 1 d . . . . .
H30 H 0.4978 0.8602 0.9978 0.019 Uiso 1 1 calc R U . . .
C29 C 0.4155(4) 0.5510(4) 1.2964(3) 0.0147(8) Uani 1 1 d . . . . .
H29 H 0.3455 0.5671 1.3193 0.018 Uiso 1 1 calc R U . . .
C28 C 0.8193(4) 0.5876(4) 1.1789(3) 0.0133(8) Uani 1 1 d . . . . .
C27 C 0.7746(4) 0.6721(4) 1.1126(3) 0.0156(9) Uani 1 1 d . . . . .
H27 H 0.6932 0.6592 1.0759 0.019 Uiso 1 1 calc R U . . .
C26 C 0.5009(4) 1.0638(4) 1.1477(3) 0.0134(8) Uani 1 1 d . . . . .
C25 C 0.8465(4) 0.5489(4) 1.4149(3) 0.0129(8) Uani 1 1 d . . . . .
C24 C 0.8094(4) 0.6157(4) 1.4788(3) 0.0135(8) Uani 1 1 d . . . . .
H24 H 0.7410 0.5866 1.4996 0.016 Uiso 1 1 calc R U . . .
C23 C 0.9302(4) 1.0808(4) 1.2372(3) 0.0152(9) Uani 1 1 d . . . . .
C22 C 0.9800(4) 0.7663(4) 1.4840(3) 0.0162(9) Uani 1 1 d . . . . .
H22 H 1.0236 0.8392 1.5062 0.019 Uiso 1 1 calc R U . . .
C21 C 0.9417(4) 0.6082(4) 1.2344(3) 0.0133(8) Uani 1 1 d . . . . .
C20 C 0.5656(4) 1.0146(4) 1.3938(3) 0.0137(9) Uani 1 1 d . . . . .
C19 C 0.8471(4) 0.7738(4) 1.0996(3) 0.0178(9) Uani 1 1 d . . . . .
H19 H 0.8146 0.8294 1.0554 0.021 Uiso 1 1 calc R U . . .
C18 C 0.3909(4) 0.8341(4) 1.0835(3) 0.0125(8) Uani 1 1 d . . . . .
C17 C 0.9546(4) 0.5896(4) 1.3868(3) 0.0136(8) Uani 1 1 d . . . . .
C16 C 0.4392(4) 0.8027(4) 1.4341(3) 0.0204(9) Uani 1 1 d . . . . .
H16 H 0.3963 0.7326 1.4476 0.025 Uiso 1 1 calc R U . . .
C15 C 0.8735(4) 0.7243(4) 1.5114(2) 0.0139(8) Uani 1 1 d . . . . .
C14 C 0.7629(4) 0.4378(4) 1.3766(3) 0.0139(8) Uani 1 1 d . . . . .
H14A H 0.8116 0.3843 1.3476 0.017 Uiso 1 1 calc R U . . .
H14B H 0.7419 0.3890 1.4216 0.017 Uiso 1 1 calc R U . . .
C13 C 0.7106(4) 1.1399(4) 1.2372(3) 0.0132(8) Uani 1 1 d . . . . .
C12 C 0.3573(4) 0.8886(4) 1.1516(3) 0.0144(8) Uani 1 1 d . . . . .
H12 H 0.2972 0.8492 1.1756 0.017 Uiso 1 1 calc R U . . .
C11 C 0.8103(4) 1.1288(4) 1.1960(3) 0.0144(8) Uani 1 1 d . . . . .
H11 H 0.7956 1.1543 1.1399 0.017 Uiso 1 1 calc R U . . .
C10 C 0.5626(4) 0.8334(4) 1.4825(3) 0.0152(9) Uani 1 1 d . . . . .
C9 C 0.6262(4) 0.5003(4) 1.2287(3) 0.0123(8) Uani 1 1 d . . . . .
C8 C 0.4053(4) 0.5744(4) 1.2118(3) 0.0125(8) Uani 1 1 d . . . . .
C7 C 0.6380(4) 0.4789(4) 1.3146(3) 0.0125(8) Uani 1 1 d . . . . .
C6 C 0.8577(4) 1.0583(4) 1.3631(3) 0.0158(9) Uani 1 1 d . . . . .
H6 H 0.8747 1.0359 1.4199 0.019 Uiso 1 1 calc R U . . .
C5 C 0.5098(4) 0.5461(4) 1.1775(3) 0.0124(8) Uani 1 1 d . . . . .
H5 H 0.5016 0.5579 1.1200 0.015 Uiso 1 1 calc R U . . .
C4 C 0.5777(4) 1.1799(4) 1.1844(3) 0.0149(8) Uani 1 1 d . . . . .
H4A H 0.5874 1.2348 1.1390 0.018 Uiso 1 1 calc R U . . .
H4B H 0.5319 1.2255 1.2194 0.018 Uiso 1 1 calc R U . . .
C3 C 0.4131(4) 1.0027(4) 1.1849(3) 0.0127(8) Uani 1 1 d . . . . .
C2 C 0.9695(4) 0.7918(4) 1.1537(3) 0.0164(9) Uani 1 1 d . . . . .
C1 C 0.3809(4) 0.8765(5) 1.3660(3) 0.0192(9) Uani 1 1 d . . . . .
H1 H 0.2976 0.8561 1.3345 0.023 Uiso 1 1 calc R U . . .
O6 O 1.0328(3) 1.0775(3) 1.19795(19) 0.0195(7) 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
Cl1 C41 1.760(5) 2_747 ?
O1 C15 1.388(5) . ?
O1 C43 1.417(5) . ?
Cl2 C41 1.766(5) 2_747 ?
O2 C8 1.374(5) . ?
O2 C46 1.415(5) . ?
O3 C18 1.387(5) . ?
O3 C46 1.406(5) . ?
O4 C10 1.384(5) . ?
O4 C43 1.410(6) . ?
O5 C2 1.395(5) . ?
O5 C34 1.401(5) . ?
C45 C20 1.520(6) . ?
C45 C35 1.523(6) . ?
C44 C20 1.399(6) . ?
C44 C1 1.406(6) . ?
C44 C42 1.509(6) . ?
C42 C3 1.522(6) . ?
C41 Cl1 1.760(5) 2_757 ?
C41 Cl2 1.766(5) 2_757 ?
C40 C22 1.374(6) . ?
C40 C17 1.401(6) . ?
C39 C21 1.514(6) . ?
C39 C17 1.510(6) . ?
C38 C28 1.518(6) . ?
C38 C9 1.521(5) . ?
C37 C2 1.376(6) . ?
C37 C21 1.394(6) . ?
C36 C10 1.392(6) . ?
C36 C20 1.397(6) . ?
C35 C6 1.396(6) . ?
C35 C13 1.403(6) . ?
C34 O6 1.406(5) . ?
C33 C23 1.382(6) . ?
C33 C6 1.388(6) . ?
C32 C30 1.374(6) . ?
C32 C26 1.400(6) . ?
C31 C29 1.381(6) . ?
C31 C7 1.403(6) . ?
C30 C18 1.397(6) . ?
C29 C8 1.380(6) . ?
C28 C27 1.397(6) . ?
C28 C21 1.402(6) . ?
C27 C19 1.376(6) . ?
C26 C3 1.396(6) . ?
C26 C4 1.519(6) . ?
C25 C24 1.401(6) . ?
C25 C17 1.408(6) . ?
C25 C14 1.517(6) . ?
C24 C15 1.378(6) . ?
C23 C11 1.381(6) . ?
C23 O6 1.398(5) . ?
C22 C15 1.392(6) . ?
C19 C2 1.389(6) . ?
C18 C12 1.379(6) . ?
C16 C1 1.374(7) . ?
C16 C10 1.389(6) . ?
C14 C7 1.516(6) . ?
C13 C11 1.397(6) . ?
C13 C4 1.517(6) . ?
C12 C3 1.401(6) . ?
C9 C5 1.394(6) . ?
C9 C7 1.397(6) . ?
C8 C5 1.398(6) . ?

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
C15 O1 C43 119.7(3) . . ?
C8 O2 C46 121.8(3) . . ?
C18 O3 C46 120.6(3) . . ?
C10 O4 C43 122.1(3) . . ?
C2 O5 C34 119.3(3) . . ?
O3 C46 O2 116.4(3) . . ?
C20 C45 C35 115.6(3) . . ?
C20 C44 C1 117.9(4) . . ?
C20 C44 C42 123.7(4) . . ?
C1 C44 C42 118.4(4) . . ?
O4 C43 O1 115.5(3) . . ?
C44 C42 C3 112.7(3) . . ?
Cl1 C41 Cl2 111.7(2) 2_757 2_757 ?
C22 C40 C17 122.5(4) . . ?
C21 C39 C17 109.2(3) . . ?
C28 C38 C9 115.1(3) . . ?
C2 C37 C21 121.5(4) . . ?
C10 C36 C20 120.2(4) . . ?
C6 C35 C13 118.7(4) . . ?
C6 C35 C45 117.9(4) . . ?
C13 C35 C45 123.2(4) . . ?
O5 C34 O6 111.2(3) . . ?
C23 C33 C6 118.7(4) . . ?
C30 C32 C26 122.0(4) . . ?
C29 C31 C7 121.8(4) . . ?
C32 C30 C18 119.2(4) . . ?
C8 C29 C31 119.8(4) . . ?
C27 C28 C21 118.6(4) . . ?
C27 C28 C38 118.6(4) . . ?
C21 C28 C38 122.8(4) . . ?
C19 C27 C28 122.2(4) . . ?
C3 C26 C32 118.2(4) . . ?
C3 C26 C4 124.0(4) . . ?
C32 C26 C4 117.5(4) . . ?
C24 C25 C17 119.6(4) . . ?
C24 C25 C14 117.2(4) . . ?
C17 C25 C14 123.2(4) . . ?
C15 C24 C25 120.6(4) . . ?
C33 C23 C11 120.5(4) . . ?
C33 C23 O6 118.2(4) . . ?
C11 C23 O6 121.1(4) . . ?
C40 C22 C15 118.8(4) . . ?
C37 C21 C28 118.8(4) . . ?
C37 C21 C39 117.6(4) . . ?
C28 C21 C39 123.5(4) . . ?
C44 C20 C36 120.3(4) . . ?
C44 C20 C45 122.4(4) . . ?
C36 C20 C45 117.3(4) . . ?
C27 C19 C2 118.8(4) . . ?
C12 C18 O3 125.1(4) . . ?
C12 C18 C30 120.0(4) . . ?
O3 C18 C30 114.8(3) . . ?
C40 C17 C25 117.9(4) . . ?
C40 C17 C39 118.2(4) . . ?
C25 C17 C39 123.6(4) . . ?
C1 C16 C10 119.6(4) . . ?
C24 C15 O1 125.6(4) . . ?
C24 C15 C22 120.6(4) . . ?
O1 C15 C22 113.8(4) . . ?
C7 C14 C25 111.9(3) . . ?
C11 C13 C35 118.9(4) . . ?
C11 C13 C4 117.4(4) . . ?
C35 C13 C4 123.5(4) . . ?
C18 C12 C3 120.5(4) . . ?
C23 C11 C13 121.1(4) . . ?
O4 C10 C16 114.5(4) . . ?
O4 C10 C36 125.6(4) . . ?
C16 C10 C36 119.9(4) . . ?
C5 C9 C7 120.0(4) . . ?
C5 C9 C38 117.0(4) . . ?
C7 C9 C38 123.1(4) . . ?
O2 C8 C29 114.5(3) . . ?
O2 C8 C5 126.0(4) . . ?
C29 C8 C5 119.5(4) . . ?
C9 C7 C31 118.2(4) . . ?
C9 C7 C14 124.0(3) . . ?
C31 C7 C14 117.8(4) . . ?
C33 C6 C35 121.9(4) . . ?
C9 C5 C8 120.7(4) . . ?
C13 C4 C26 109.0(3) . . ?
C26 C3 C12 119.9(4) . . ?
C26 C3 C42 123.2(4) . . ?
C12 C3 C42 116.9(4) . . ?
C37 C2 C19 120.1(4) . . ?
C37 C2 O5 116.0(4) . . ?
C19 C2 O5 123.6(4) . . ?
C16 C1 C44 121.9(4) . . ?
C23 O6 C34 117.2(3) . . ?

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.063

_shelxl_version_number           2013-4



_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_cr111-
_database_code_depnum_ccdc_archive 'CCDC 1537585'
_audit_update_record             
;
2017-03-13 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C45 H36 O6, C5 H5 N'
_chemical_formula_sum            'C50 H41 N O6'
_chemical_formula_weight         751.84

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   10.5518(5)
_cell_length_b                   10.7827(5)
_cell_length_c                   32.7161(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3722.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    80
_cell_measurement_reflns_used    27190
_cell_measurement_theta_min      4.2740
_cell_measurement_theta_max      66.8910

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear intense colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             1584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3230
_exptl_crystal_size_mid          0.1838
_exptl_crystal_size_min          0.0921
_exptl_absorpt_coefficient_mu    0.701
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.717
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_diffrn_ambient_temperature      80
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_reflns_number            63817
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_av_R_equivalents  0.1755
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         4.317
_diffrn_reflns_theta_max         67.790
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             6606
_reflns_number_gt                6155
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_max     0.975
_reflns_Friedel_fraction_full    0.977

_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       'Gemini, (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXLe  (Sheldrick, 2011)'
_computing_publication_material  'SHELXLe  (Sheldrick, 2011)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0744P)²+1.0885P] 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     SHELXL
_refine_ls_extinction_coef       0.0025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2487 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.04(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6606
_refine_ls_number_parameters     515
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1269
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
C1 C 1.0304(3) 0.0476(4) 0.16304(10) 0.0217(7) Uani 1 1 d . . . . .
H1 H 1.0988 0.0848 0.1761 0.026 Uiso 1 1 calc R U . . .
C2 C 0.7093(3) -0.0999(3) 0.09831(9) 0.0191(7) Uani 1 1 d . . . . .
H2A H 0.7377 -0.1537 0.0764 0.023 Uiso 1 1 calc R U . . .
H2B H 0.6503 -0.1459 0.1153 0.023 Uiso 1 1 calc R U . . .
O1 O 1.1908(2) 0.2168(2) 0.07031(7) 0.0210(5) Uani 1 1 d . . . . .
C3 C 0.5854(3) 0.5712(3) 0.17857(9) 0.0172(7) Uani 1 1 d . . . . .
H3 H 0.5689 0.5852 0.2061 0.021 Uiso 1 1 calc R U . . .
C4 C 0.9367(3) -0.0410(3) 0.10314(9) 0.0177(7) Uani 1 1 d . . . . .
H4 H 0.9447 -0.0674 0.0762 0.021 Uiso 1 1 calc R U . . .
C5 C 0.4345(3) 0.1926(4) 0.18639(10) 0.0236(8) Uani 1 1 d . . . . .
H5 H 0.3620 0.2111 0.1714 0.028 Uiso 1 1 calc R U . . .
C6 C 0.6299(3) 0.5368(3) 0.09596(8) 0.0143(6) Uani 1 1 d . . . . .
H6 H 0.6434 0.5280 0.0680 0.017 Uiso 1 1 calc R U . . .
O2 O 1.1543(2) 0.0286(3) 0.10257(7) 0.0260(6) Uani 1 1 d . . . . .
O3 O 0.8181(2) 0.2755(2) 0.28334(6) 0.0217(5) Uani 1 1 d . . . . .
O4 O 0.6006(2) 0.3249(2) 0.27243(7) 0.0239(6) Uani 1 1 d . . . . .
O5 O 0.4177(2) 0.4439(2) 0.09197(6) 0.0188(5) Uani 1 1 d . . . . .
O6 O 0.5315(2) 0.3581(2) 0.03557(6) 0.0185(5) Uani 1 1 d . . . . .
C7 C 1.0389(3) 0.0142(3) 0.12264(10) 0.0202(7) Uani 1 1 d . . . . .
C8 C 0.7047(3) 0.6004(3) 0.16292(9) 0.0155(6) Uani 1 1 d . . . . .
C9 C 1.1221(3) 0.3823(3) 0.11216(9) 0.0166(7) Uani 1 1 d . . . . .
H9 H 1.1933 0.3691 0.1283 0.020 Uiso 1 1 calc R U . . .
C10 C 0.8507(3) 0.6144(3) 0.10052(8) 0.0165(7) Uani 1 1 d . . . . .
H10A H 0.8945 0.6770 0.1165 0.020 Uiso 1 1 calc R U . . .
H10B H 0.8338 0.6494 0.0738 0.020 Uiso 1 1 calc R U . . .
C11 C 0.8726(3) 0.3547(3) 0.25509(8) 0.0183(7) Uani 1 1 d . . . . .
C12 C 0.4970(3) 0.1853(3) 0.08335(9) 0.0177(7) Uani 1 1 d . . . . .
H12 H 0.4255 0.2223 0.0947 0.021 Uiso 1 1 calc R U . . .
C13 C 1.0979(3) 0.3040(3) 0.07963(9) 0.0165(7) Uani 1 1 d . . . . .
C14 C 1.0412(3) 0.4806(3) 0.12108(8) 0.0155(7) Uani 1 1 d . . . . .
C15 C 0.5733(3) 0.2396(3) 0.24217(9) 0.0204(7) Uani 1 1 d . . . . .
C16 C 0.9903(3) 0.3160(3) 0.24094(9) 0.0195(7) Uani 1 1 d . . . . .
H16 H 1.0270 0.2435 0.2508 0.023 Uiso 1 1 calc R U . . .
C17 C 0.9979(3) 0.4940(3) 0.19542(9) 0.0173(7) Uani 1 1 d . . . . .
C18 C 0.8794(3) 0.5320(3) 0.20990(8) 0.0159(7) Uani 1 1 d . . . . .
C19 C 0.4911(3) 0.5216(3) 0.15405(9) 0.0177(7) Uani 1 1 d . . . . .
H19 H 0.4126 0.5016 0.1651 0.021 Uiso 1 1 calc R U . . .
C20 C 0.5148(3) 0.5021(3) 0.11294(9) 0.0156(6) Uani 1 1 d . . . . .
C21 C 0.5405(3) 0.0723(3) 0.09892(9) 0.0175(7) Uani 1 1 d . . . . .
C22 C 0.6122(3) 0.0603(3) 0.19945(9) 0.0193(7) Uani 1 1 d . . . . .
C23 C 0.6614(3) 0.1842(3) 0.03239(9) 0.0190(7) Uani 1 1 d . . . . .
H23 H 0.7021 0.2211 0.0103 0.023 Uiso 1 1 calc R U . . .
C24 C 0.8068(3) 0.6417(3) 0.19274(9) 0.0166(7) Uani 1 1 d . . . . .
H24A H 0.8653 0.6969 0.1789 0.020 Uiso 1 1 calc R U . . .
H24B H 0.7680 0.6873 0.2150 0.020 Uiso 1 1 calc R U . . .
C25 C 1.0515(3) 0.3868(3) 0.21201(9) 0.0192(7) Uani 1 1 d . . . . .
H25 H 1.1315 0.3624 0.2032 0.023 Uiso 1 1 calc R U . . .
C26 C 0.4661(3) 0.2673(4) 0.21911(9) 0.0237(8) Uani 1 1 d . . . . .
H26 H 0.4162 0.3355 0.2257 0.028 Uiso 1 1 calc R U . . .
C27 C 0.8190(3) 0.4631(3) 0.24053(8) 0.0165(7) Uani 1 1 d . . . . .
H27 H 0.7423 0.4905 0.2512 0.020 Uiso 1 1 calc R U . . .
C28 C 0.5075(3) 0.0904(3) 0.17503(9) 0.0203(7) Uani 1 1 d . . . . .
C29 C 0.6962(3) -0.0516(3) 0.19118(9) 0.0194(7) Uani 1 1 d . . . . .
H29A H 0.7237 -0.0854 0.2172 0.023 Uiso 1 1 calc R U . . .
H29B H 0.6456 -0.1147 0.1777 0.023 Uiso 1 1 calc R U . . .
C30 C 0.4727(3) 0.0207(3) 0.13648(9) 0.0206(7) Uani 1 1 d . . . . .
H30A H 0.3818 0.0259 0.1323 0.025 Uiso 1 1 calc R U . . .
H30B H 0.4946 -0.0661 0.1398 0.025 Uiso 1 1 calc R U . . .
C31 C 0.8129(3) -0.0267(3) 0.16515(9) 0.0177(7) Uani 1 1 d . . . . .
C32 C 0.6996(4) 0.3043(4) 0.30048(10) 0.0260(8) Uani 1 1 d . . . . .
H32A H 0.7091 0.3781 0.3172 0.031 Uiso 1 1 calc R U . . .
H32B H 0.6750 0.2370 0.3185 0.031 Uiso 1 1 calc R U . . .
C33 C 0.7259(3) 0.5851(3) 0.12101(9) 0.0149(6) Uani 1 1 d . . . . .
C34 C 1.1544(3) 0.0927(3) 0.06507(9) 0.0210(7) Uani 1 1 d . . . . .
H34A H 1.2124 0.0524 0.0463 0.025 Uiso 1 1 calc R U . . .
H34B H 1.0702 0.0897 0.0532 0.025 Uiso 1 1 calc R U . . .
C35 C 0.3593(4) 0.7743(4) 0.06459(11) 0.0315(9) Uani 1 1 d . . . . .
H35 H 0.4256 0.7756 0.0833 0.038 Uiso 1 1 calc R U . . .
C36 C 0.1609(4) 0.6981(4) 0.04157(11) 0.0327(9) Uani 1 1 d . . . . .
H36 H 0.0904 0.6470 0.0444 0.039 Uiso 1 1 calc R U . . .
C37 C 0.2565(4) 0.6965(4) 0.07030(11) 0.0325(9) Uani 1 1 d . . . . .
H37 H 0.2520 0.6445 0.0929 0.039 Uiso 1 1 calc R U . . .
C38 C 0.1722(4) 0.7771(4) 0.00856(10) 0.0323(9) Uani 1 1 d . . . . .
H38 H 0.1072 0.7775 -0.0107 0.039 Uiso 1 1 calc R U . . .
C39 C 0.4246(3) 0.4244(3) 0.04962(9) 0.0193(7) Uani 1 1 d . . . . .
H39A H 0.4234 0.5046 0.0362 0.023 Uiso 1 1 calc R U . . .
H39B H 0.3490 0.3801 0.0411 0.023 Uiso 1 1 calc R U . . .
C40 C 0.8218(3) -0.0572(3) 0.12370(9) 0.0166(6) Uani 1 1 d . . . . .
C41 C 0.5591(3) 0.2426(3) 0.05135(8) 0.0156(6) Uani 1 1 d . . . . .
C42 C 0.7009(3) 0.0707(4) 0.04694(9) 0.0206(7) Uani 1 1 d . . . . .
H42 H 0.7673 0.0304 0.0338 0.025 Uiso 1 1 calc R U . . .
C43 C 0.6448(3) 0.0142(3) 0.08076(9) 0.0176(7) Uani 1 1 d . . . . .
C44 C 0.3615(4) 0.8493(4) 0.03079(11) 0.0284(8) Uani 1 1 d . . . . .
H44 H 0.4310 0.9012 0.0273 0.034 Uiso 1 1 calc R U . . .
N1 N 0.2698(3) 0.8526(3) 0.00252(9) 0.0303(7) Uani 1 1 d . . . . .
C45 C 1.0668(3) 0.5544(3) 0.15986(9) 0.0173(7) Uani 1 1 d . . . . .
H45A H 1.1571 0.5564 0.1653 0.021 Uiso 1 1 calc R U . . .
H45B H 1.0375 0.6390 0.1564 0.021 Uiso 1 1 calc R U . . .
C46 C 0.9185(3) 0.0253(3) 0.18415(9) 0.0198(7) Uani 1 1 d . . . . .
H46 H 0.9140 0.0455 0.2117 0.024 Uiso 1 1 calc R U . . .
C47 C 0.9918(3) 0.3213(3) 0.05507(9) 0.0182(7) Uani 1 1 d . . . . .
H47 H 0.9739 0.2672 0.0337 0.022 Uiso 1 1 calc R U . . .
C48 C 0.9136(3) 0.4213(3) 0.06324(9) 0.0176(7) Uani 1 1 d . . . . .
H48 H 0.8431 0.4344 0.0467 0.021 Uiso 1 1 calc R U . . .
C49 C 0.9370(3) 0.5033(3) 0.09554(8) 0.0148(6) Uani 1 1 d . . . . .
C50 C 0.6437(3) 0.1344(3) 0.23303(9) 0.0193(7) Uani 1 1 d . . . . .
H50 H 0.7124 0.1130 0.2494 0.023 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
C1 C7 1.373(5) . ?
C1 C46 1.388(5) . ?
C2 C43 1.518(5) . ?
C2 C40 1.520(4) . ?
O1 C13 1.392(4) . ?
O1 C34 1.403(4) . ?
C3 C19 1.386(4) . ?
C3 C8 1.395(5) . ?
C4 C7 1.387(5) . ?
C4 C40 1.398(4) . ?
C5 C26 1.380(5) . ?
C5 C28 1.395(5) . ?
C6 C20 1.386(4) . ?
C6 C33 1.404(4) . ?
O2 C7 1.392(4) . ?
O2 C34 1.408(4) . ?
O3 C11 1.384(4) . ?
O3 C32 1.405(4) . ?
O4 C15 1.382(4) . ?
O4 C32 1.408(4) . ?
O5 C20 1.383(4) . ?
O5 C39 1.403(4) . ?
O6 C41 1.380(4) . ?
O6 C39 1.412(4) . ?
C8 C33 1.399(4) . ?
C8 C24 1.520(4) . ?
C9 C13 1.382(5) . ?
C9 C14 1.392(5) . ?
C10 C33 1.511(4) . ?
C10 C49 1.514(5) . ?
C11 C27 1.382(5) . ?
C11 C16 1.390(5) . ?
C12 C41 1.381(4) . ?
C12 C21 1.398(5) . ?
C13 C47 1.391(4) . ?
C14 C49 1.402(4) . ?
C14 C45 1.522(4) . ?
C15 C50 1.389(5) . ?
C15 C26 1.392(5) . ?
C16 C25 1.377(5) . ?
C17 C25 1.396(5) . ?
C17 C18 1.399(4) . ?
C17 C45 1.518(4) . ?
C18 C27 1.401(4) . ?
C18 C24 1.516(4) . ?
C19 C20 1.384(4) . ?
C21 C43 1.399(5) . ?
C21 C30 1.527(4) . ?
C22 C50 1.398(5) . ?
C22 C28 1.402(5) . ?
C22 C29 1.522(5) . ?
C23 C42 1.377(5) . ?
C23 C41 1.395(5) . ?
C28 C30 1.513(5) . ?
C29 C31 1.521(4) . ?
C31 C46 1.394(5) . ?
C31 C40 1.399(4) . ?
C35 C44 1.370(6) . ?
C35 C37 1.383(6) . ?
C36 C37 1.379(6) . ?
C36 C38 1.381(6) . ?
C38 N1 1.327(5) . ?
C42 C43 1.395(5) . ?
C44 N1 1.339(5) . ?
C47 C48 1.383(5) . ?
C48 C49 1.400(5) . ?

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
C7 C1 C46 119.3(3) . . ?
C43 C2 C40 108.1(3) . . ?
C13 O1 C34 118.5(2) . . ?
C19 C3 C8 121.5(3) . . ?
C7 C4 C40 120.4(3) . . ?
C26 C5 C28 122.3(3) . . ?
C20 C6 C33 119.9(3) . . ?
C7 O2 C34 117.8(2) . . ?
C11 O3 C32 120.0(3) . . ?
C15 O4 C32 121.1(3) . . ?
C20 O5 C39 121.3(2) . . ?
C41 O6 C39 120.3(2) . . ?
C1 C7 C4 120.3(3) . . ?
C1 C7 O2 118.8(3) . . ?
C4 C7 O2 120.7(3) . . ?
C3 C8 C33 118.5(3) . . ?
C3 C8 C24 118.0(3) . . ?
C33 C8 C24 123.4(3) . . ?
C13 C9 C14 120.9(3) . . ?
C33 C10 C49 114.0(3) . . ?
C27 C11 O3 125.6(3) . . ?
C27 C11 C16 120.3(3) . . ?
O3 C11 C16 114.1(3) . . ?
C41 C12 C21 120.7(3) . . ?
C9 C13 C47 120.7(3) . . ?
C9 C13 O1 116.8(3) . . ?
C47 C13 O1 122.1(3) . . ?
C9 C14 C49 119.2(3) . . ?
C9 C14 C45 117.7(3) . . ?
C49 C14 C45 123.0(3) . . ?
O4 C15 C50 125.9(3) . . ?
O4 C15 C26 114.5(3) . . ?
C50 C15 C26 119.6(3) . . ?
C25 C16 C11 118.8(3) . . ?
C25 C17 C18 118.2(3) . . ?
C25 C17 C45 117.3(3) . . ?
C18 C17 C45 124.2(3) . . ?
C17 C18 C27 119.5(3) . . ?
C17 C18 C24 123.7(3) . . ?
C27 C18 C24 116.7(3) . . ?
C3 C19 C20 119.4(3) . . ?
O5 C20 C19 114.6(3) . . ?
O5 C20 C6 124.9(3) . . ?
C19 C20 C6 120.4(3) . . ?
C12 C21 C43 119.6(3) . . ?
C12 C21 C30 117.2(3) . . ?
C43 C21 C30 123.2(3) . . ?
C50 C22 C28 120.2(3) . . ?
C50 C22 C29 117.0(3) . . ?
C28 C22 C29 122.8(3) . . ?
C42 C23 C41 118.8(3) . . ?
C18 C24 C8 111.6(3) . . ?
C16 C25 C17 122.4(3) . . ?
C5 C26 C15 119.4(3) . . ?
C11 C27 C18 120.6(3) . . ?
C5 C28 C22 117.8(3) . . ?
C5 C28 C30 118.7(3) . . ?
C22 C28 C30 123.5(3) . . ?
C31 C29 C22 115.5(3) . . ?
C28 C30 C21 112.1(3) . . ?
C46 C31 C40 118.2(3) . . ?
C46 C31 C29 118.0(3) . . ?
C40 C31 C29 123.8(3) . . ?
O3 C32 O4 115.8(2) . . ?
C8 C33 C6 120.0(3) . . ?
C8 C33 C10 123.4(3) . . ?
C6 C33 C10 116.6(3) . . ?
O1 C34 O2 111.2(3) . . ?
C44 C35 C37 118.7(3) . . ?
C37 C36 C38 118.5(4) . . ?
C36 C37 C35 118.3(3) . . ?
N1 C38 C36 124.2(3) . . ?
O5 C39 O6 116.0(2) . . ?
C4 C40 C31 119.7(3) . . ?
C4 C40 C2 116.9(3) . . ?
C31 C40 C2 123.3(3) . . ?
O6 C41 C12 126.0(3) . . ?
O6 C41 C23 113.9(3) . . ?
C12 C41 C23 120.2(3) . . ?
C23 C42 C43 122.3(3) . . ?
C42 C43 C21 118.3(3) . . ?
C42 C43 C2 117.7(3) . . ?
C21 C43 C2 123.7(3) . . ?
N1 C44 C35 124.1(4) . . ?
C38 N1 C44 116.2(3) . . ?
C17 C45 C14 109.2(3) . . ?
C1 C46 C31 121.9(3) . . ?
C48 C47 C13 118.3(3) . . ?
C47 C48 C49 122.2(3) . . ?
C48 C49 C14 118.6(3) . . ?
C48 C49 C10 118.3(3) . . ?
C14 C49 C10 123.1(3) . . ?
C15 C50 C22 120.6(3) . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.064

_shelxl_version_number           2013-4



_exptl_crystal_recrystallization_method 'From the Melt'
