# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_dm13504_0m
_database_code_depnum_ccdc_archive 'CCDC 961159'
_audit_update_record             
;
2013-09-16 deposited with the CCDC.
2015-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H22 O4'
_chemical_formula_weight         446.47

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           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                   7.07170(10)
_cell_length_b                   8.84390(10)
_cell_length_c                   19.5443(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.5560(10)
_cell_angle_gamma                90
_cell_volume                     1214.33(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    4599
_cell_measurement_theta_min      4.55
_cell_measurement_theta_max      69.10

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.647
_shelx_estimated_absorpt_T_min   0.850
_shelx_estimated_absorpt_T_max   0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5648
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9496
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.275
_diffrn_reflns_theta_max         69.837
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_point_group_measured_fraction_full 0.917
_reflns_number_total             4122
_reflns_number_gt                4005
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_max     0.813
_reflns_Friedel_fraction_full    0.844

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1932P)²+0.6934P] 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       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1633 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.17(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4122
_refine_ls_number_parameters     348
_refine_ls_number_restraints     161
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0746
_refine_ls_wR_factor_ref         0.2278
_refine_ls_wR_factor_gt          0.2230
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0718(5) 0.7228(4) 0.80656(18) 0.0383(8) Uani 1 1 d . . . . .
O2 O -0.2061(5) 0.5147(5) 0.7567(2) 0.0495(10) Uani 1 1 d . . . . .
O3 O -0.0727(8) 0.7325(6) 0.6424(2) 0.0625(13) Uani 1 1 d . . . . .
O4 O 0.0782(8) 0.6238(5) 0.5610(2) 0.0647(14) Uani 1 1 d D . . . .
C1 C 0.2067(6) 0.4032(5) 0.7797(2) 0.0246(9) Uani 1 1 d . . . . .
H1A H 0.0965 0.3322 0.7707 0.030 Uiso 1 1 calc R U . . .
C2 C 0.3500(7) 0.3557(5) 0.7305(2) 0.0309(10) Uani 1 1 d . . . . .
H2A H 0.4798 0.3920 0.7468 0.037 Uiso 1 1 calc R U . . .
H2B H 0.3528 0.2445 0.7250 0.037 Uiso 1 1 calc R U . . .
C3 C 0.2724(7) 0.4328(6) 0.6639(2) 0.0355(11) Uani 1 1 d . . . . .
H3A H 0.3080 0.4077 0.6199 0.043 Uiso 1 1 calc R U . . .
C4 C 0.1479(7) 0.5402(5) 0.6750(2) 0.0340(10) Uani 1 1 d . . . . .
C5 C 0.1329(6) 0.5614(5) 0.7511(2) 0.0268(9) Uani 1 1 d . . . . .
C6 C -0.0689(6) 0.5911(6) 0.7689(2) 0.0341(10) Uani 1 1 d . . . . .
C7 C 0.2354(6) 0.7011(5) 0.7799(2) 0.0250(9) Uani 1 1 d . . . . .
C8 C 0.4184(6) 0.7543(5) 0.7772(2) 0.0297(9) Uani 1 1 d . . . . .
H8A H 0.5073 0.6976 0.7548 0.036 Uiso 1 1 calc R U . . .
C9 C 0.4698(7) 0.8923(5) 0.8081(2) 0.0344(10) Uani 1 1 d . . . . .
H9A H 0.5954 0.9297 0.8070 0.041 Uiso 1 1 calc R U . . .
C10 C 0.3398(8) 0.9756(5) 0.8403(3) 0.0391(12) Uani 1 1 d . . . . .
H10A H 0.3777 1.0693 0.8614 0.047 Uiso 1 1 calc R U . . .
C11 C 0.1537(8) 0.9242(6) 0.8424(3) 0.0386(11) Uani 1 1 d . . . . .
H11A H 0.0629 0.9807 0.8640 0.046 Uiso 1 1 calc R U . . .
C12 C 0.1093(6) 0.7880(5) 0.8115(2) 0.0301(10) Uani 1 1 d . . . . .
C13 C 0.2695(6) 0.3940(4) 0.8562(2) 0.0236(8) Uani 1 1 d . . . . .
C14 C 0.1488(6) 0.3265(4) 0.9024(2) 0.0258(9) Uani 1 1 d . . . . .
C15 C -0.0374(7) 0.2724(5) 0.8823(2) 0.0320(10) Uani 1 1 d . . . . .
H15A H -0.0903 0.2832 0.8356 0.038 Uiso 1 1 calc R U . . .
C16 C -0.1444(8) 0.2048(6) 0.9282(3) 0.0417(12) Uani 1 1 d . . . . .
H16A H -0.2688 0.1692 0.9129 0.050 Uiso 1 1 calc R U . . .
C17 C -0.0712(9) 0.1881(6) 0.9974(3) 0.0443(13) Uani 1 1 d . . . . .
H17A H -0.1454 0.1411 1.0290 0.053 Uiso 1 1 calc R U . . .
C18 C 0.1079(9) 0.2401(6) 1.0194(3) 0.0430(12) Uani 1 1 d . . . . .
H18A H 0.1576 0.2283 1.0664 0.052 Uiso 1 1 calc R U . . .
C19 C 0.2205(7) 0.3114(5) 0.9729(2) 0.0307(10) Uani 1 1 d . . . . .
C20 C 0.4026(8) 0.3670(6) 0.9968(2) 0.0364(11) Uani 1 1 d . . . . .
H20A H 0.4491 0.3568 1.0441 0.044 Uiso 1 1 calc R U . . .
C21 C 0.5135(7) 0.4353(6) 0.9530(2) 0.0339(10) Uani 1 1 d . . . . .
H21A H 0.6349 0.4747 0.9700 0.041 Uiso 1 1 calc R U . . .
C22 C 0.4460(6) 0.4467(5) 0.8823(2) 0.0286(9) Uani 1 1 d . . . . .
H22A H 0.5249 0.4921 0.8519 0.034 Uiso 1 1 calc R U . . .
C23 C 0.0395(10) 0.6425(6) 0.6256(3) 0.0469(14) Uani 1 1 d . . . . .
C24 C -0.0238(17) 0.7258(11) 0.5094(4) 0.070(3) Uani 0.679(9) 1 d D U P A 1
H24A H 0.0639 0.7647 0.4775 0.084 Uiso 0.679(9) 1 calc R U P A 1
H24B H -0.0781 0.8128 0.5324 0.084 Uiso 0.679(9) 1 calc R U P A 1
C25 C -0.1801(11) 0.6335(7) 0.4707(3) 0.076(2) Uani 0.679(9) 1 d DG U P A 1
C26 C -0.1536(12) 0.5726(8) 0.4069(3) 0.074(3) Uani 0.679(9) 1 d DG U P A 1
H26A H -0.0370 0.5886 0.3882 0.088 Uiso 0.679(9) 1 calc R U P A 1
C27 C -0.2976(15) 0.4884(8) 0.3706(3) 0.094(3) Uani 0.679(9) 1 d G U P A 1
H27A H -0.2795 0.4469 0.3270 0.113 Uiso 0.679(9) 1 calc R U P A 1
C28 C -0.4681(13) 0.4650(9) 0.3980(4) 0.111(4) Uani 0.679(9) 1 d G U P A 1
H28A H -0.5666 0.4075 0.3731 0.134 Uiso 0.679(9) 1 calc R U P A 1
C29 C -0.4947(12) 0.5258(10) 0.4618(4) 0.114(4) Uani 0.679(9) 1 d G U P A 1
H29A H -0.6113 0.5098 0.4805 0.137 Uiso 0.679(9) 1 calc R U P A 1
C30 C -0.3507(13) 0.6101(9) 0.4981(3) 0.102(4) Uani 0.679(9) 1 d DG U P A 1
H30A H -0.3688 0.6516 0.5417 0.122 Uiso 0.679(9) 1 calc R U P A 1
C24' C -0.055(3) 0.693(3) 0.5070(7) 0.075(4) Uani 0.321(9) 1 d D U P A 2
H24C H -0.0816 0.7982 0.5196 0.090 Uiso 0.321(9) 1 calc R U P A 2
H24D H -0.1769 0.6361 0.5024 0.090 Uiso 0.321(9) 1 calc R U P A 2
C25' C 0.028(2) 0.6898(16) 0.4397(6) 0.071(3) Uani 0.321(9) 1 d DG U P A 2
C26' C 0.184(2) 0.7810(16) 0.4309(7) 0.090(5) Uani 0.321(9) 1 d DG U P A 2
H26B H 0.2307 0.8503 0.4660 0.108 Uiso 0.321(9) 1 calc R U P A 2
C27' C 0.271(2) 0.7707(19) 0.3708(8) 0.093(6) Uani 0.321(9) 1 d G U P A 2
H27B H 0.3772 0.8330 0.3648 0.111 Uiso 0.321(9) 1 calc R U P A 2
C28' C 0.203(3) 0.6693(19) 0.3195(7) 0.063(4) Uani 0.321(9) 1 d G U P A 2
H28B H 0.2621 0.6623 0.2785 0.076 Uiso 0.321(9) 1 calc R U P A 2
C29' C 0.047(3) 0.5781(17) 0.3284(6) 0.081(5) Uani 0.321(9) 1 d G U P A 2
H29B H 0.0003 0.5088 0.2933 0.097 Uiso 0.321(9) 1 calc R U P A 2
C30' C -0.040(2) 0.5884(16) 0.3885(7) 0.073(4) Uani 0.321(9) 1 d DG U P A 2
H30B H -0.1462 0.5260 0.3945 0.087 Uiso 0.321(9) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.379(6) . ?
O1 C12 1.398(6) . ?
O2 C6 1.184(6) . ?
O3 C23 1.197(8) . ?
O4 C23 1.332(7) . ?
O4 C24' 1.465(13) . ?
O4 C24 1.479(9) . ?
C1 C13 1.512(6) . ?
C1 C2 1.534(6) . ?
C1 C5 1.573(6) . ?
C1 H1A 1.0000 . ?
C2 C3 1.516(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.329(7) . ?
C3 H3A 0.9500 . ?
C4 C23 1.473(7) . ?
C4 C5 1.516(6) . ?
C5 C7 1.509(6) . ?
C5 C6 1.530(6) . ?
C7 C12 1.375(6) . ?
C7 C8 1.383(6) . ?
C8 C9 1.391(7) . ?
C8 H8A 0.9500 . ?
C9 C10 1.385(7) . ?
C9 H9A 0.9500 . ?
C10 C11 1.397(8) . ?
C10 H10A 0.9500 . ?
C11 C12 1.367(7) . ?
C11 H11A 0.9500 . ?
C13 C22 1.374(6) . ?
C13 C14 1.440(6) . ?
C14 C15 1.414(7) . ?
C14 C19 1.420(6) . ?
C15 C16 1.374(7) . ?
C15 H15A 0.9500 . ?
C16 C17 1.400(8) . ?
C16 H16A 0.9500 . ?
C17 C18 1.370(9) . ?
C17 H17A 0.9500 . ?
C18 C19 1.423(7) . ?
C18 H18A 0.9500 . ?
C19 C20 1.407(7) . ?
C20 C21 1.365(7) . ?
C20 H20A 0.9500 . ?
C21 C22 1.414(6) . ?
C21 H21A 0.9500 . ?
C22 H22A 0.9500 . ?
C24 C25 1.506(9) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.3900 . ?
C25 C30 1.3900 . ?
C26 C27 1.3900 . ?
C26 H26A 0.9500 . ?
C27 C28 1.3900 . ?
C27 H27A 0.9500 . ?
C28 C29 1.3900 . ?
C28 H28A 0.9500 . ?
C29 C30 1.3900 . ?
C29 H29A 0.9500 . ?
C30 H30A 0.9500 . ?
C24' C25' 1.503(10) . ?
C24' H24C 0.9900 . ?
C24' H24D 0.9900 . ?
C25' C26' 1.3900 . ?
C25' C30' 1.3900 . ?
C26' C27' 1.3900 . ?
C26' H26B 0.9500 . ?
C27' C28' 1.3900 . ?
C27' H27B 0.9500 . ?
C28' C29' 1.3900 . ?
C28' H28B 0.9500 . ?
C29' C30' 1.3900 . ?
C29' H29B 0.9500 . ?
C30' H30B 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 O1 C12 108.4(3) . . ?
C23 O4 C24' 116.5(8) . . ?
C23 O4 C24 115.7(6) . . ?
C13 C1 C2 117.7(4) . . ?
C13 C1 C5 116.5(3) . . ?
C2 C1 C5 103.7(3) . . ?
C13 C1 H1A 106.0 . . ?
C2 C1 H1A 106.0 . . ?
C5 C1 H1A 106.0 . . ?
C3 C2 C1 102.4(4) . . ?
C3 C2 H2A 111.3 . . ?
C1 C2 H2A 111.3 . . ?
C3 C2 H2B 111.3 . . ?
C1 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
C4 C3 C2 111.3(4) . . ?
C4 C3 H3A 124.4 . . ?
C2 C3 H3A 124.4 . . ?
C3 C4 C23 129.5(5) . . ?
C3 C4 C5 111.8(4) . . ?
C23 C4 C5 118.6(4) . . ?
C7 C5 C4 112.5(4) . . ?
C7 C5 C6 101.3(4) . . ?
C4 C5 C6 114.6(4) . . ?
C7 C5 C1 118.1(3) . . ?
C4 C5 C1 100.4(3) . . ?
C6 C5 C1 110.6(4) . . ?
O2 C6 O1 121.9(4) . . ?
O2 C6 C5 128.3(5) . . ?
O1 C6 C5 109.7(4) . . ?
C12 C7 C8 119.0(4) . . ?
C12 C7 C5 108.4(4) . . ?
C8 C7 C5 132.5(4) . . ?
C7 C8 C9 118.8(4) . . ?
C7 C8 H8A 120.6 . . ?
C9 C8 H8A 120.6 . . ?
C10 C9 C8 120.7(5) . . ?
C10 C9 H9A 119.7 . . ?
C8 C9 H9A 119.7 . . ?
C9 C10 C11 121.1(4) . . ?
C9 C10 H10A 119.5 . . ?
C11 C10 H10A 119.5 . . ?
C12 C11 C10 116.3(4) . . ?
C12 C11 H11A 121.8 . . ?
C10 C11 H11A 121.8 . . ?
C11 C12 C7 124.2(4) . . ?
C11 C12 O1 123.8(4) . . ?
C7 C12 O1 112.0(4) . . ?
C22 C13 C14 119.1(4) . . ?
C22 C13 C1 120.0(4) . . ?
C14 C13 C1 120.9(4) . . ?
C15 C14 C19 117.1(4) . . ?
C15 C14 C13 124.5(4) . . ?
C19 C14 C13 118.4(4) . . ?
C16 C15 C14 122.1(5) . . ?
C16 C15 H15A 119.0 . . ?
C14 C15 H15A 119.0 . . ?
C15 C16 C17 120.4(5) . . ?
C15 C16 H16A 119.8 . . ?
C17 C16 H16A 119.8 . . ?
C18 C17 C16 119.7(4) . . ?
C18 C17 H17A 120.2 . . ?
C16 C17 H17A 120.2 . . ?
C17 C18 C19 120.8(5) . . ?
C17 C18 H18A 119.6 . . ?
C19 C18 H18A 119.6 . . ?
C20 C19 C14 120.1(4) . . ?
C20 C19 C18 120.0(4) . . ?
C14 C19 C18 119.9(5) . . ?
C21 C20 C19 121.1(4) . . ?
C21 C20 H20A 119.5 . . ?
C19 C20 H20A 119.5 . . ?
C20 C21 C22 119.3(4) . . ?
C20 C21 H21A 120.3 . . ?
C22 C21 H21A 120.3 . . ?
C13 C22 C21 122.0(4) . . ?
C13 C22 H22A 119.0 . . ?
C21 C22 H22A 119.0 . . ?
O3 C23 O4 123.9(5) . . ?
O3 C23 C4 122.7(5) . . ?
O4 C23 C4 113.4(5) . . ?
O4 C24 C25 106.5(7) . . ?
O4 C24 H24A 110.4 . . ?
C25 C24 H24A 110.4 . . ?
O4 C24 H24B 110.4 . . ?
C25 C24 H24B 110.4 . . ?
H24A C24 H24B 108.6 . . ?
C26 C25 C30 120.0 . . ?
C26 C25 C24 119.6(5) . . ?
C30 C25 C24 120.4(5) . . ?
C27 C26 C25 120.0 . . ?
C27 C26 H26A 120.0 . . ?
C25 C26 H26A 120.0 . . ?
C28 C27 C26 120.0 . . ?
C28 C27 H27A 120.0 . . ?
C26 C27 H27A 120.0 . . ?
C29 C28 C27 120.0 . . ?
C29 C28 H28A 120.0 . . ?
C27 C28 H28A 120.0 . . ?
C28 C29 C30 120.0 . . ?
C28 C29 H29A 120.0 . . ?
C30 C29 H29A 120.0 . . ?
C29 C30 C25 120.0 . . ?
C29 C30 H30A 120.0 . . ?
C25 C30 H30A 120.0 . . ?
O4 C24' C25' 109.8(12) . . ?
O4 C24' H24C 109.7 . . ?
C25' C24' H24C 109.7 . . ?
O4 C24' H24D 109.7 . . ?
C25' C24' H24D 109.7 . . ?
H24C C24' H24D 108.2 . . ?
C26' C25' C30' 120.0 . . ?
C26' C25' C24' 119.7(5) . . ?
C30' C25' C24' 120.1(6) . . ?
C27' C26' C25' 120.0 . . ?
C27' C26' H26B 120.0 . . ?
C25' C26' H26B 120.0 . . ?
C26' C27' C28' 120.0 . . ?
C26' C27' H27B 120.0 . . ?
C28' C27' H27B 120.0 . . ?
C29' C28' C27' 120.0 . . ?
C29' C28' H28B 120.0 . . ?
C27' C28' H28B 120.0 . . ?
C28' C29' C30' 120.0 . . ?
C28' C29' H29B 120.0 . . ?
C30' C29' H29B 120.0 . . ?
C29' C30' C25' 120.0 . . ?
C29' C30' H30B 120.0 . . ?
C25' C30' H30B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 C1 C2 C3 -159.5(4) . . . . ?
C5 C1 C2 C3 -29.1(4) . . . . ?
C1 C2 C3 C4 16.3(5) . . . . ?
C2 C3 C4 C23 179.8(5) . . . . ?
C2 C3 C4 C5 4.4(6) . . . . ?
C3 C4 C5 C7 103.9(5) . . . . ?
C23 C4 C5 C7 -72.1(5) . . . . ?
C3 C4 C5 C6 -141.2(4) . . . . ?
C23 C4 C5 C6 42.9(6) . . . . ?
C3 C4 C5 C1 -22.6(5) . . . . ?
C23 C4 C5 C1 161.5(5) . . . . ?
C13 C1 C5 C7 39.5(5) . . . . ?
C2 C1 C5 C7 -91.5(4) . . . . ?
C13 C1 C5 C4 162.1(4) . . . . ?
C2 C1 C5 C4 31.1(4) . . . . ?
C13 C1 C5 C6 -76.4(4) . . . . ?
C2 C1 C5 C6 152.5(4) . . . . ?
C12 O1 C6 O2 -179.3(4) . . . . ?
C12 O1 C6 C5 3.7(5) . . . . ?
C7 C5 C6 O2 179.3(5) . . . . ?
C4 C5 C6 O2 58.0(7) . . . . ?
C1 C5 C6 O2 -54.7(6) . . . . ?
C7 C5 C6 O1 -4.0(4) . . . . ?
C4 C5 C6 O1 -125.3(4) . . . . ?
C1 C5 C6 O1 122.0(4) . . . . ?
C4 C5 C7 C12 125.6(4) . . . . ?
C6 C5 C7 C12 2.8(4) . . . . ?
C1 C5 C7 C12 -118.1(4) . . . . ?
C4 C5 C7 C8 -51.4(6) . . . . ?
C6 C5 C7 C8 -174.2(4) . . . . ?
C1 C5 C7 C8 64.9(6) . . . . ?
C12 C7 C8 C9 1.5(6) . . . . ?
C5 C7 C8 C9 178.3(4) . . . . ?
C7 C8 C9 C10 -0.6(6) . . . . ?
C8 C9 C10 C11 -0.4(7) . . . . ?
C9 C10 C11 C12 0.5(7) . . . . ?
C10 C11 C12 C7 0.5(7) . . . . ?
C10 C11 C12 O1 -177.5(4) . . . . ?
C8 C7 C12 C11 -1.5(6) . . . . ?
C5 C7 C12 C11 -179.0(4) . . . . ?
C8 C7 C12 O1 176.7(4) . . . . ?
C5 C7 C12 O1 -0.8(5) . . . . ?
C6 O1 C12 C11 176.4(4) . . . . ?
C6 O1 C12 C7 -1.8(5) . . . . ?
C2 C1 C13 C22 44.7(5) . . . . ?
C5 C1 C13 C22 -79.4(5) . . . . ?
C2 C1 C13 C14 -133.4(4) . . . . ?
C5 C1 C13 C14 102.4(4) . . . . ?
C22 C13 C14 C15 178.0(4) . . . . ?
C1 C13 C14 C15 -3.8(6) . . . . ?
C22 C13 C14 C19 -2.5(5) . . . . ?
C1 C13 C14 C19 175.6(4) . . . . ?
C19 C14 C15 C16 -1.4(6) . . . . ?
C13 C14 C15 C16 178.0(4) . . . . ?
C14 C15 C16 C17 0.4(7) . . . . ?
C15 C16 C17 C18 0.2(8) . . . . ?
C16 C17 C18 C19 0.3(8) . . . . ?
C15 C14 C19 C20 -178.1(4) . . . . ?
C13 C14 C19 C20 2.4(6) . . . . ?
C15 C14 C19 C18 1.9(6) . . . . ?
C13 C14 C19 C18 -177.6(4) . . . . ?
C17 C18 C19 C20 178.6(5) . . . . ?
C17 C18 C19 C14 -1.3(7) . . . . ?
C14 C19 C20 C21 -0.3(7) . . . . ?
C18 C19 C20 C21 179.7(5) . . . . ?
C19 C20 C21 C22 -1.6(7) . . . . ?
C14 C13 C22 C21 0.6(6) . . . . ?
C1 C13 C22 C21 -177.6(4) . . . . ?
C20 C21 C22 C13 1.5(7) . . . . ?
C24' O4 C23 O3 -14.4(14) . . . . ?
C24 O4 C23 O3 1.6(10) . . . . ?
C24' O4 C23 C4 165.2(12) . . . . ?
C24 O4 C23 C4 -178.8(6) . . . . ?
C3 C4 C23 O3 178.1(6) . . . . ?
C5 C4 C23 O3 -6.8(9) . . . . ?
C3 C4 C23 O4 -1.6(9) . . . . ?
C5 C4 C23 O4 173.5(5) . . . . ?
C23 O4 C24 C25 -103.5(7) . . . . ?
C24' O4 C24 C25 -7(3) . . . . ?
O4 C24 C25 C26 -98.9(7) . . . . ?
O4 C24 C25 C30 81.6(8) . . . . ?
C30 C25 C26 C27 0.0 . . . . ?
C24 C25 C26 C27 -179.4(7) . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C26 C27 C28 C29 0.0 . . . . ?
C27 C28 C29 C30 0.0 . . . . ?
C28 C29 C30 C25 0.0 . . . . ?
C26 C25 C30 C29 0.0 . . . . ?
C24 C25 C30 C29 179.4(7) . . . . ?
C23 O4 C24' C25' 168.2(8) . . . . ?
C24 O4 C24' C25' 78(3) . . . . ?
O4 C24' C25' C26' -69.2(18) . . . . ?
O4 C24' C25' C30' 106.0(14) . . . . ?
C30' C25' C26' C27' 0.0 . . . . ?
C24' C25' C26' C27' 175.2(14) . . . . ?
C25' C26' C27' C28' 0.0 . . . . ?
C26' C27' C28' C29' 0.0 . . . . ?
C27' C28' C29' C30' 0.0 . . . . ?
C28' C29' C30' C25' 0.0 . . . . ?
C26' C25' C30' C29' 0.0 . . . . ?
C24' C25' C30' C29' -175.1(14) . . . . ?

_refine_diff_density_max         1.215
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.084

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_cd213569
_database_code_depnum_ccdc_archive 'CCDC 967550'
_audit_update_record             
;
2013-10-21 deposited with the CCDC.
2015-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38.50 H29 Cl O4'
_chemical_formula_weight         591.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   16.8074(19)
_cell_length_b                   10.9989(12)
_cell_length_c                   16.649(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.018(3)
_cell_angle_gamma                90
_cell_volume                     3075.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             1236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    0.165
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.24178
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9347
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.213
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 0.904
_reflns_number_total             5478
_reflns_number_gt                3947
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_max     0.796
_reflns_Friedel_fraction_full    0.799

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0776P)²+0.1360P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1313 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.06(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5478
_refine_ls_number_parameters     418
_refine_ls_number_restraints     85
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1527
_refine_ls_wR_factor_gt          0.1364
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.044
_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 0.91599(10) 0.99636(17) 0.98027(10) 0.1128(6) Uani 1 1 d . . . . .
O1 O 1.0360(3) -0.0405(4) 0.7322(4) 0.132(2) Uani 1 1 d . . . . .
O2 O 1.0664(2) 0.0816(5) 0.6316(3) 0.1056(14) Uani 1 1 d . . . . .
O3 O 0.8881(2) 0.4044(4) 0.9396(2) 0.1039(13) Uani 1 1 d . . . . .
O4 O 0.81875(17) 0.2482(3) 0.89018(18) 0.0790(9) Uani 1 1 d . . . . .
C1 C 1.0456(2) 0.2688(4) 0.6878(2) 0.0624(11) Uani 1 1 d . . . . .
C2 C 1.0462(3) 0.3922(5) 0.6847(3) 0.0747(12) Uani 1 1 d . . . . .
H2 H 1.0314 0.4377 0.7288 0.090 Uiso 1 1 calc R U . . .
C3 C 1.0693(4) 0.4505(7) 0.6143(4) 0.1021(19) Uani 1 1 d . . . . .
H3 H 1.0696 0.5350 0.6117 0.122 Uiso 1 1 calc R U . . .
C4 C 1.0913(4) 0.3846(13) 0.5501(4) 0.132(3) Uani 1 1 d . . . . .
H4 H 1.1070 0.4248 0.5041 0.159 Uiso 1 1 calc R U . . .
C5 C 1.0908(4) 0.2610(11) 0.5512(4) 0.119(3) Uani 1 1 d . . . . .
H5 H 1.1049 0.2157 0.5068 0.143 Uiso 1 1 calc R U . . .
C6 C 1.0685(3) 0.2063(7) 0.6209(3) 0.0863(17) Uani 1 1 d . . . . .
C7 C 1.0431(3) 0.0604(5) 0.7081(4) 0.0870(17) Uani 1 1 d . . . . .
C8 C 1.0271(2) 0.1787(4) 0.7515(2) 0.0589(10) Uani 1 1 d . . . . .
C9 C 0.9404(2) 0.1799(4) 0.7823(2) 0.0567(9) Uani 1 1 d . . . . .
H9 H 0.9306 0.0992 0.8048 0.068 Uiso 1 1 calc R U . . .
C10 C 0.9494(2) 0.2665(4) 0.8526(2) 0.0569(9) Uani 1 1 d . . . . .
C11 C 1.0248(2) 0.2725(4) 0.8792(2) 0.0627(10) Uani 1 1 d . . . . .
H11 H 1.0426 0.3207 0.9220 0.075 Uiso 1 1 calc R U . . .
C12 C 1.0772(2) 0.1929(4) 0.8320(2) 0.0613(10) Uani 1 1 d . . . . .
H12 H 1.0769 0.1131 0.8582 0.074 Uiso 1 1 calc R U . . .
C13 C 1.1638(2) 0.2283(4) 0.8260(2) 0.0643(11) Uani 1 1 d . . . . .
C14 C 1.1882(3) 0.3474(5) 0.8317(3) 0.0703(12) Uani 1 1 d . . . . .
H14 H 1.1507 0.4086 0.8377 0.084 Uiso 1 1 calc R U . . .
C15 C 1.2676(3) 0.3768(6) 0.8287(3) 0.0862(15) Uani 1 1 d . . . . .
H15 H 1.2829 0.4580 0.8315 0.103 Uiso 1 1 calc R U . . .
C16 C 1.3235(3) 0.2901(7) 0.8218(3) 0.0977(18) Uani 1 1 d . . . . .
H16 H 1.3771 0.3107 0.8208 0.117 Uiso 1 1 calc R U . . .
C17 C 1.3001(4) 0.1722(8) 0.8163(4) 0.109(2) Uani 1 1 d . . . . .
H17 H 1.3381 0.1117 0.8107 0.131 Uiso 1 1 calc R U . . .
C18 C 1.2207(3) 0.1404(5) 0.8189(3) 0.0874(15) Uani 1 1 d . . . . .
H18 H 1.2059 0.0591 0.8159 0.105 Uiso 1 1 calc R U . . .
C19 C 0.8835(3) 0.3159(5) 0.8981(2) 0.0672(11) Uani 1 1 d . . . . .
C20 C 0.7511(3) 0.2842(8) 0.9362(3) 0.105(2) Uani 1 1 d . . . . .
H23A H 0.7439 0.3717 0.9347 0.126 Uiso 0.6 1 d R U P A 1
H23B H 0.7578 0.2583 0.9917 0.126 Uiso 0.6 1 d R U P A 1
H23C H 0.7501 0.3713 0.9361 0.126 Uiso 0.4 1 d R U P B 2
H23D H 0.7594 0.2564 0.9904 0.126 Uiso 0.4 1 d R U P B 2
C21 C 0.67964(18) 0.2185(4) 0.8941(2) 0.071(2) Uani 0.6 1 d G U P C 1
C22 C 0.6681(3) 0.2419(5) 0.8125(2) 0.078(2) Uani 0.6 1 d G U P C 1
H22 H 0.7072 0.2821 0.7845 0.093 Uiso 0.6 1 calc R U P C 1
C23 C 0.5981(3) 0.2053(5) 0.7726(3) 0.082(2) Uani 0.6 1 d G U P C 1
H23 H 0.5904 0.2209 0.7180 0.099 Uiso 0.6 1 calc R U P C 1
C24 C 0.5397(2) 0.1452(5) 0.8143(4) 0.082(2) Uani 0.6 1 d G U P C 1
H24 H 0.4928 0.1207 0.7876 0.098 Uiso 0.6 1 calc R U P C 1
C25 C 0.5512(2) 0.1218(4) 0.8959(4) 0.080(2) Uani 0.6 1 d G U P C 1
H25 H 0.5121 0.0817 0.9239 0.096 Uiso 0.6 1 calc R U P C 1
C26 C 0.6212(3) 0.1585(4) 0.9358(2) 0.079(2) Uani 0.6 1 d G U P C 1
H26 H 0.6289 0.1428 0.9904 0.095 Uiso 0.6 1 calc R U P C 1
C21' C 0.6782(2) 0.2390(4) 0.9063(2) 0.061(3) Uani 0.4 1 d G U P C 2
C22' C 0.6430(3) 0.2666(4) 0.8317(3) 0.069(3) Uani 0.4 1 d G U P C 2
H22' H 0.6665 0.3235 0.7987 0.082 Uiso 0.4 1 calc R U P C 2
C23' C 0.5728(2) 0.2093(4) 0.8066(3) 0.071(2) Uani 0.4 1 d G U P C 2
H23' H 0.5492 0.2278 0.7567 0.085 Uiso 0.4 1 calc R U P C 2
C24' C 0.5377(2) 0.1243(5) 0.8561(4) 0.065(2) Uani 0.4 1 d G U P C 2
H24' H 0.4907 0.0859 0.8392 0.078 Uiso 0.4 1 calc R U P C 2
C25' C 0.5729(3) 0.0967(4) 0.9306(4) 0.072(3) Uani 0.4 1 d G U P C 2
H25' H 0.5495 0.0398 0.9637 0.086 Uiso 0.4 1 calc R U P C 2
C26' C 0.6432(3) 0.1540(4) 0.9558(2) 0.073(3) Uani 0.4 1 d G U P C 2
H26' H 0.6667 0.1355 1.0057 0.088 Uiso 0.4 1 calc R U P C 2
C27 C 0.8755(2) 0.2023(3) 0.7193(2) 0.0515(9) Uani 1 1 d . . . . .
C28 C 0.8499(2) 0.3168(4) 0.6970(2) 0.0592(10) Uani 1 1 d . . . . .
H28 H 0.8718 0.3844 0.7229 0.071 Uiso 1 1 calc R U . . .
C29 C 0.7924(2) 0.3328(4) 0.6369(2) 0.0567(9) Uani 1 1 d . . . . .
H29 H 0.7759 0.4112 0.6234 0.068 Uiso 1 1 calc R U . . .
C30 C 0.7583(2) 0.2343(4) 0.5959(2) 0.0527(9) Uani 1 1 d . . . . .
C31 C 0.7839(2) 0.1197(4) 0.6195(2) 0.0608(10) Uani 1 1 d . . . . .
H31 H 0.7618 0.0516 0.5941 0.073 Uiso 1 1 calc R U . . .
C32 C 0.8411(2) 0.1043(4) 0.6794(2) 0.0581(9) Uani 1 1 d . . . . .
H32 H 0.8571 0.0260 0.6935 0.070 Uiso 1 1 calc R U . . .
C33 C 0.6998(2) 0.2514(4) 0.5288(2) 0.0606(10) Uani 1 1 d . . . . .
C34 C 0.6968(4) 0.1725(5) 0.4649(3) 0.0943(17) Uani 1 1 d . . . . .
H34 H 0.7317 0.1069 0.4645 0.113 Uiso 1 1 calc R U . . .
C35 C 0.6432(4) 0.1887(6) 0.4015(4) 0.1153(19) Uani 1 1 d . U . . .
H35 H 0.6416 0.1327 0.3596 0.138 Uiso 1 1 calc R U . . .
C36 C 0.5932(4) 0.2837(6) 0.3990(4) 0.1044(16) Uani 1 1 d . U . . .
H36 H 0.5576 0.2942 0.3555 0.125 Uiso 1 1 calc R U . . .
C37 C 0.5950(3) 0.3642(6) 0.4607(4) 0.0968(16) Uani 1 1 d . U . . .
H37 H 0.5606 0.4306 0.4593 0.116 Uiso 1 1 calc R U . . .
C38 C 0.6477(3) 0.3484(5) 0.5257(3) 0.0765(13) Uani 1 1 d . . . . .
H38 H 0.6479 0.4038 0.5679 0.092 Uiso 1 1 calc R U . . .
C39 C 1.0000 0.9097(10) 1.0000 0.159(5) Uani 1 2 d S T P . .
H39A H 1.0090 0.8577 0.9541 0.190 Uiso 0.5 1 calc R U P . .
H39B H 0.9910 0.8577 1.0459 0.190 Uiso 0.5 1 calc R U P . .


_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 C39 1.726(6) . ?
O1 C7 1.187(7) . ?
O2 C7 1.365(8) . ?
O2 C6 1.384(8) . ?
O3 C19 1.195(6) . ?
O4 C19 1.321(5) . ?
O4 C20 1.448(6) . ?
C1 C2 1.359(7) . ?
C1 C6 1.376(6) . ?
C1 C8 1.492(6) . ?
C2 C3 1.403(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.354(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.360(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(10) . ?
C5 H5 0.9300 . ?
C7 C8 1.516(7) . ?
C8 C9 1.562(6) . ?
C8 C12 1.567(5) . ?
C9 C27 1.506(5) . ?
C9 C10 1.513(6) . ?
C9 H9 0.9800 . ?
C10 C11 1.329(5) . ?
C10 C19 1.468(6) . ?
C11 C12 1.486(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.513(6) . ?
C12 H12 0.9800 . ?
C13 C18 1.367(7) . ?
C13 C14 1.375(7) . ?
C14 C15 1.375(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.346(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.358(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(9) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C20 C21' 1.398(6) . ?
C20 C21 1.548(7) . ?
C20 H23A 0.9700 . ?
C20 H23B 0.9700 . ?
C20 H23C 0.9580 . ?
C20 H23D 0.9590 . ?
C21 C22 1.3900 . ?
C21 C26 1.3900 . ?
C22 C23 1.3900 . ?
C22 H22 0.9300 . ?
C23 C24 1.3900 . ?
C23 H23 0.9300 . ?
C24 C25 1.3900 . ?
C24 H24 0.9300 . ?
C25 C26 1.3900 . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C21' C22' 1.3900 . ?
C21' C26' 1.3900 . ?
C22' C23' 1.3900 . ?
C22' H22' 0.9300 . ?
C23' C24' 1.3900 . ?
C23' H23' 0.9300 . ?
C24' C25' 1.3900 . ?
C24' H24' 0.9300 . ?
C25' C26' 1.3900 . ?
C25' H25' 0.9300 . ?
C26' H26' 0.9300 . ?
C27 C28 1.378(6) . ?
C27 C32 1.382(5) . ?
C28 C29 1.378(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.392(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.385(6) . ?
C30 C33 1.475(5) . ?
C31 C32 1.371(5) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 C34 1.372(6) . ?
C33 C38 1.380(6) . ?
C34 C35 1.375(7) . ?
C34 H34 0.9300 . ?
C35 C36 1.342(9) . ?
C35 H35 0.9300 . ?
C36 C37 1.355(9) . ?
C36 H36 0.9300 . ?
C37 C38 1.386(7) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 Cl1 1.726(6) 2_757 ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?

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 O2 C6 107.4(4) . . ?
C19 O4 C20 116.9(4) . . ?
C2 C1 C6 117.7(5) . . ?
C2 C1 C8 133.9(4) . . ?
C6 C1 C8 108.4(5) . . ?
C1 C2 C3 119.4(5) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 120.4(8) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.5(7) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 116.9(6) . . ?
C4 C5 H5 121.5 . . ?
C6 C5 H5 121.5 . . ?
C5 C6 C1 124.0(7) . . ?
C5 C6 O2 123.6(6) . . ?
C1 C6 O2 112.4(5) . . ?
O1 C7 O2 120.6(6) . . ?
O1 C7 C8 128.3(7) . . ?
O2 C7 C8 111.1(5) . . ?
C1 C8 C7 100.7(4) . . ?
C1 C8 C9 116.6(3) . . ?
C7 C8 C9 110.3(4) . . ?
C1 C8 C12 115.0(3) . . ?
C7 C8 C12 113.2(3) . . ?
C9 C8 C12 101.4(3) . . ?
C27 C9 C10 119.2(3) . . ?
C27 C9 C8 115.7(3) . . ?
C10 C9 C8 101.0(3) . . ?
C27 C9 H9 106.7 . . ?
C10 C9 H9 106.7 . . ?
C8 C9 H9 106.7 . . ?
C11 C10 C19 122.6(4) . . ?
C11 C10 C9 111.0(4) . . ?
C19 C10 C9 125.1(4) . . ?
C10 C11 C12 111.8(4) . . ?
C10 C11 H11 124.1 . . ?
C12 C11 H11 124.1 . . ?
C11 C12 C13 118.2(4) . . ?
C11 C12 C8 101.5(3) . . ?
C13 C12 C8 117.3(3) . . ?
C11 C12 H12 106.3 . . ?
C13 C12 H12 106.3 . . ?
C8 C12 H12 106.3 . . ?
C18 C13 C14 118.2(4) . . ?
C18 C13 C12 120.0(4) . . ?
C14 C13 C12 121.7(4) . . ?
C13 C14 C15 120.5(5) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 121.2(6) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 118.7(5) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C16 C17 C18 121.2(6) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C13 C18 C17 120.2(6) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
O3 C19 O4 123.6(4) . . ?
O3 C19 C10 124.4(4) . . ?
O4 C19 C10 112.0(4) . . ?
C21' C20 O4 114.2(5) . . ?
O4 C20 C21 104.1(4) . . ?
O4 C20 H23A 110.9 . . ?
C21 C20 H23A 110.9 . . ?
O4 C20 H23B 110.9 . . ?
C21 C20 H23B 110.9 . . ?
H23A C20 H23B 109.0 . . ?
C21' C20 H23C 109.9 . . ?
O4 C20 H23C 106.7 . . ?
C21' C20 H23D 108.5 . . ?
O4 C20 H23D 108.7 . . ?
H23C C20 H23D 108.8 . . ?
C22 C21 C26 120.0 . . ?
C22 C21 C20 115.8(3) . . ?
C26 C21 C20 123.1(3) . . ?
C21 C22 C23 120.0 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C26 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 120.0 . . ?
C25 C26 H26 120.0 . . ?
C21 C26 H26 120.0 . . ?
C22' C21' C26' 120.0 . . ?
C22' C21' C20 125.5(4) . . ?
C26' C21' C20 114.4(4) . . ?
C21' C22' C23' 120.0 . . ?
C21' C22' H22' 120.0 . . ?
C23' C22' H22' 120.0 . . ?
C24' C23' C22' 120.0 . . ?
C24' C23' H23' 120.0 . . ?
C22' C23' H23' 120.0 . . ?
C25' C24' C23' 120.0 . . ?
C25' C24' H24' 120.0 . . ?
C23' C24' H24' 120.0 . . ?
C24' C25' C26' 120.0 . . ?
C24' C25' H25' 120.0 . . ?
C26' C25' H25' 120.0 . . ?
C25' C26' C21' 120.0 . . ?
C25' C26' H26' 120.0 . . ?
C21' C26' H26' 120.0 . . ?
C28 C27 C32 117.4(3) . . ?
C28 C27 C9 123.3(3) . . ?
C32 C27 C9 119.2(3) . . ?
C29 C28 C27 121.2(3) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C28 C29 C30 121.4(4) . . ?
C28 C29 H29 119.3 . . ?
C30 C29 H29 119.3 . . ?
C31 C30 C29 116.9(3) . . ?
C31 C30 C33 121.5(3) . . ?
C29 C30 C33 121.6(3) . . ?
C32 C31 C30 121.4(3) . . ?
C32 C31 H31 119.3 . . ?
C30 C31 H31 119.3 . . ?
C31 C32 C27 121.7(3) . . ?
C31 C32 H32 119.2 . . ?
C27 C32 H32 119.2 . . ?
C34 C33 C38 117.0(4) . . ?
C34 C33 C30 120.8(4) . . ?
C38 C33 C30 122.1(4) . . ?
C33 C34 C35 121.2(5) . . ?
C33 C34 H34 119.4 . . ?
C35 C34 H34 119.4 . . ?
C36 C35 C34 121.2(6) . . ?
C36 C35 H35 119.4 . . ?
C34 C35 H35 119.4 . . ?
C35 C36 C37 119.3(5) . . ?
C35 C36 H36 120.4 . . ?
C37 C36 H36 120.4 . . ?
C36 C37 C38 120.4(5) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
C33 C38 C37 120.9(5) . . ?
C33 C38 H38 119.6 . . ?
C37 C38 H38 119.6 . . ?
Cl1 C39 Cl1 112.9(6) . 2_757 ?
Cl1 C39 H39A 109.0 . . ?
Cl1 C39 H39A 109.0 2_757 . ?
Cl1 C39 H39B 109.0 . . ?
Cl1 C39 H39B 109.0 2_757 . ?
H39A C39 H39B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.4(7) . . . . ?
C8 C1 C2 C3 178.1(4) . . . . ?
C1 C2 C3 C4 -0.3(8) . . . . ?
C2 C3 C4 C5 0.8(11) . . . . ?
C3 C4 C5 C6 -1.2(12) . . . . ?
C4 C5 C6 C1 1.3(10) . . . . ?
C4 C5 C6 O2 -178.9(6) . . . . ?
C2 C1 C6 C5 -0.9(7) . . . . ?
C8 C1 C6 C5 -179.2(5) . . . . ?
C2 C1 C6 O2 179.3(4) . . . . ?
C8 C1 C6 O2 1.0(5) . . . . ?
C7 O2 C6 C5 178.9(5) . . . . ?
C7 O2 C6 C1 -1.3(5) . . . . ?
C6 O2 C7 O1 179.4(5) . . . . ?
C6 O2 C7 C8 1.0(5) . . . . ?
C2 C1 C8 C7 -178.2(5) . . . . ?
C6 C1 C8 C7 -0.3(4) . . . . ?
C2 C1 C8 C9 62.4(6) . . . . ?
C6 C1 C8 C9 -119.7(4) . . . . ?
C2 C1 C8 C12 -56.1(6) . . . . ?
C6 C1 C8 C12 121.7(4) . . . . ?
O1 C7 C8 C1 -178.7(5) . . . . ?
O2 C7 C8 C1 -0.4(4) . . . . ?
O1 C7 C8 C9 -54.9(6) . . . . ?
O2 C7 C8 C9 123.4(4) . . . . ?
O1 C7 C8 C12 58.0(7) . . . . ?
O2 C7 C8 C12 -123.7(4) . . . . ?
C1 C8 C9 C27 38.2(5) . . . . ?
C7 C8 C9 C27 -75.9(5) . . . . ?
C12 C8 C9 C27 163.9(3) . . . . ?
C1 C8 C9 C10 -91.9(4) . . . . ?
C7 C8 C9 C10 154.0(4) . . . . ?
C12 C8 C9 C10 33.8(4) . . . . ?
C27 C9 C10 C11 -150.1(3) . . . . ?
C8 C9 C10 C11 -22.3(4) . . . . ?
C27 C9 C10 C19 43.1(6) . . . . ?
C8 C9 C10 C19 170.9(4) . . . . ?
C19 C10 C11 C12 167.2(4) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
C10 C11 C12 C13 152.1(3) . . . . ?
C10 C11 C12 C8 22.3(4) . . . . ?
C1 C8 C12 C11 92.7(4) . . . . ?
C7 C8 C12 C11 -152.3(4) . . . . ?
C9 C8 C12 C11 -34.1(4) . . . . ?
C1 C8 C12 C13 -37.7(5) . . . . ?
C7 C8 C12 C13 77.4(5) . . . . ?
C9 C8 C12 C13 -164.5(4) . . . . ?
C11 C12 C13 C18 149.1(4) . . . . ?
C8 C12 C13 C18 -88.8(5) . . . . ?
C11 C12 C13 C14 -27.3(6) . . . . ?
C8 C12 C13 C14 94.8(5) . . . . ?
C18 C13 C14 C15 1.3(7) . . . . ?
C12 C13 C14 C15 177.8(4) . . . . ?
C13 C14 C15 C16 -1.4(8) . . . . ?
C14 C15 C16 C17 1.2(8) . . . . ?
C15 C16 C17 C18 -1.0(10) . . . . ?
C14 C13 C18 C17 -1.1(7) . . . . ?
C12 C13 C18 C17 -177.7(5) . . . . ?
C16 C17 C18 C13 1.0(9) . . . . ?
C20 O4 C19 O3 -1.3(7) . . . . ?
C20 O4 C19 C10 176.5(4) . . . . ?
C11 C10 C19 O3 33.7(7) . . . . ?
C9 C10 C19 O3 -161.0(5) . . . . ?
C11 C10 C19 O4 -144.1(4) . . . . ?
C9 C10 C19 O4 21.3(6) . . . . ?
C19 O4 C20 C21' 159.0(5) . . . . ?
C19 O4 C20 C21 161.7(4) . . . . ?
C21' C20 C21 C22 110.3(2) . . . . ?
O4 C20 C21 C22 -56.0(6) . . . . ?
C21' C20 C21 C26 -57.8(5) . . . . ?
O4 C20 C21 C26 135.9(4) . . . . ?
C26 C21 C22 C23 0.0 . . . . ?
C20 C21 C22 C23 -168.5(5) . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C24 C25 C26 C21 0.0 . . . . ?
C22 C21 C26 C25 0.0 . . . . ?
C20 C21 C26 C25 167.6(5) . . . . ?
O4 C20 C21' C22' -63.4(8) . . . . ?
C21 C20 C21' C22' -77.9(3) . . . . ?
O4 C20 C21' C26' 112.5(5) . . . . ?
C21 C20 C21' C26' 97.9(3) . . . . ?
C26' C21' C22' C23' 0.0 . . . . ?
C20 C21' C22' C23' 175.6(6) . . . . ?
C21' C22' C23' C24' 0.0 . . . . ?
C22' C23' C24' C25' 0.0 . . . . ?
C23' C24' C25' C26' 0.0 . . . . ?
C24' C25' C26' C21' 0.0 . . . . ?
C22' C21' C26' C25' 0.0 . . . . ?
C20 C21' C26' C25' -176.1(5) . . . . ?
C10 C9 C27 C28 33.1(6) . . . . ?
C8 C9 C27 C28 -87.6(5) . . . . ?
C10 C9 C27 C32 -149.1(4) . . . . ?
C8 C9 C27 C32 90.3(4) . . . . ?
C32 C27 C28 C29 -0.2(6) . . . . ?
C9 C27 C28 C29 177.6(4) . . . . ?
C27 C28 C29 C30 -0.6(6) . . . . ?
C28 C29 C30 C31 1.2(6) . . . . ?
C28 C29 C30 C33 -176.8(4) . . . . ?
C29 C30 C31 C32 -1.1(6) . . . . ?
C33 C30 C31 C32 176.9(4) . . . . ?
C30 C31 C32 C27 0.4(7) . . . . ?
C28 C27 C32 C31 0.3(6) . . . . ?
C9 C27 C32 C31 -177.6(4) . . . . ?
C31 C30 C33 C34 -31.9(7) . . . . ?
C29 C30 C33 C34 146.0(5) . . . . ?
C31 C30 C33 C38 150.2(4) . . . . ?
C29 C30 C33 C38 -31.9(6) . . . . ?
C38 C33 C34 C35 -1.1(8) . . . . ?
C30 C33 C34 C35 -179.1(5) . . . . ?
C33 C34 C35 C36 1.5(11) . . . . ?
C34 C35 C36 C37 -0.8(11) . . . . ?
C35 C36 C37 C38 -0.3(10) . . . . ?
C34 C33 C38 C37 0.0(7) . . . . ?
C30 C33 C38 C37 178.0(5) . . . . ?
C36 C37 C38 C33 0.7(8) . . . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_dm14382_0m
_database_code_depnum_ccdc_archive 'CCDC 1010550'
_audit_update_record             
;
2014-06-26 deposited with the CCDC.
2015-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H23 N O4'
_chemical_formula_weight         425.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
N N 0.0311 0.0180 '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                   8.16260(10)
_cell_length_b                   12.2302(2)
_cell_length_c                   11.07420(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.4020(10)
_cell_angle_gamma                90
_cell_volume                     1083.72(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    6378
_cell_measurement_theta_min      4.07
_cell_measurement_theta_max      68.94

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.707
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5683
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7473
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.072
_diffrn_reflns_theta_max         69.357
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.814
_diffrn_reflns_point_group_measured_fraction_full 0.828
_reflns_number_total             3297
_reflns_number_gt                3271
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.580
_reflns_Friedel_fraction_max     0.629
_reflns_Friedel_fraction_full    0.645

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0691P)²+0.1082P] 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_abs_structure_details 
; 
 Flack x determined using 1193 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.13(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3297
_refine_ls_number_parameters     291
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1765(2) 0.55077(13) 0.47125(16) 0.0261(4) Uani 1 1 d . . . . .
O2 O 0.5708(2) 0.63352(14) 0.30940(16) 0.0292(4) Uani 1 1 d . . . . .
O3 O 0.39590(19) 0.72275(16) 0.68078(15) 0.0311(4) Uani 1 1 d . . . . .
O4 O 0.2243(2) 0.74247(18) 0.81590(14) 0.0341(4) Uani 1 1 d . . . . .
N1 N 0.3345(2) 0.67178(15) 0.37931(15) 0.0181(4) Uani 1 1 d . . . . .
C1 C 0.2097(2) 0.64248(18) 0.44340(18) 0.0185(4) Uani 1 1 d . . . . .
C2 C 0.1191(2) 0.74556(17) 0.47137(18) 0.0180(4) Uani 1 1 d . . . . .
C3 C 0.2202(3) 0.83498(18) 0.42726(18) 0.0183(4) Uani 1 1 d . . . . .
C4 C 0.2041(3) 0.94741(18) 0.4337(2) 0.0234(5) Uani 1 1 d . . . . .
H4 H 0.1215 0.9788 0.4727 0.028 Uiso 1 1 calc R U . . .
C5 C 0.3110(3) 1.0137(2) 0.3823(2) 0.0258(5) Uani 1 1 d . . . . .
H5 H 0.3015 1.0910 0.3856 0.031 Uiso 1 1 calc R U . . .
C6 C 0.4316(3) 0.9664(2) 0.3261(2) 0.0246(5) Uani 1 1 d . . . . .
H6 H 0.5028 1.0124 0.2903 0.030 Uiso 1 1 calc R U . . .
C7 C 0.4510(3) 0.8535(2) 0.32064(19) 0.0228(5) Uani 1 1 d . . . . .
H7 H 0.5347 0.8220 0.2829 0.027 Uiso 1 1 calc R U . . .
C8 C 0.3435(2) 0.78886(18) 0.37244(17) 0.0179(4) Uani 1 1 d . . . . .
C9 C 0.4459(3) 0.59864(19) 0.33713(18) 0.0199(4) Uani 1 1 d . . . . .
C10 C 0.3982(3) 0.48007(19) 0.3257(2) 0.0284(5) Uani 1 1 d . . . . .
H10A H 0.4669 0.4425 0.2753 0.043 Uiso 1 1 calc R U . . .
H10B H 0.2800 0.4734 0.2866 0.043 Uiso 1 1 calc R U . . .
H10C H 0.4167 0.4468 0.4078 0.043 Uiso 1 1 calc R U . . .
C11 C 0.1074(3) 0.75356(17) 0.60593(18) 0.0200(4) Uani 1 1 d . . . . .
C12 C -0.0457(3) 0.77945(18) 0.62048(19) 0.0216(4) Uani 1 1 d . . . . .
H12 H -0.0755 0.7891 0.6985 0.026 Uiso 1 1 calc R U . . .
C13 C -0.1658(3) 0.79174(18) 0.50020(19) 0.0200(4) Uani 1 1 d . . . . .
H13A H -0.1883 0.8698 0.4795 0.024 Uiso 1 1 calc R U . . .
H13B H -0.2728 0.7542 0.5019 0.024 Uiso 1 1 calc R U . . .
C14 C -0.0724(2) 0.73642(18) 0.40780(18) 0.0182(4) Uani 1 1 d . . . . .
H14 H -0.1017 0.6570 0.4066 0.022 Uiso 1 1 calc R U . . .
C15 C -0.1159(2) 0.77594(19) 0.27512(19) 0.0206(4) Uani 1 1 d . . . . .
C16 C -0.1472(3) 0.8839(2) 0.2493(2) 0.0265(5) Uani 1 1 d . . . . .
H16 H -0.1403 0.9343 0.3154 0.032 Uiso 1 1 calc R U . . .
C17 C -0.1895(3) 0.9228(2) 0.1268(2) 0.0372(6) Uani 1 1 d . . . . .
H17 H -0.2098 0.9985 0.1113 0.045 Uiso 1 1 calc R U . . .
C18 C -0.2010(3) 0.8517(3) 0.0314(2) 0.0392(6) Uani 1 1 d . . . . .
H18 H -0.2300 0.8783 -0.0507 0.047 Uiso 1 1 calc R U . . .
C19 C -0.1707(3) 0.7395(3) 0.0516(2) 0.0316(5) Uani 1 1 d . . . . .
C20 C -0.1848(3) 0.6631(3) -0.0481(2) 0.0437(7) Uani 1 1 d . . . . .
H20 H -0.2158 0.6891 -0.1303 0.052 Uiso 1 1 calc R U . . .
C21 C -0.1552(4) 0.5552(3) -0.0285(2) 0.0452(7) Uani 1 1 d . . . . .
H21 H -0.1651 0.5064 -0.0963 0.054 Uiso 1 1 calc R U . . .
C22 C -0.1092(3) 0.5152(3) 0.0934(2) 0.0386(6) Uani 1 1 d . . . . .
H22 H -0.0879 0.4394 0.1075 0.046 Uiso 1 1 calc R U . . .
C23 C -0.0952(3) 0.5858(2) 0.1914(2) 0.0284(5) Uani 1 1 d . . . . .
H23 H -0.0641 0.5576 0.2727 0.034 Uiso 1 1 calc R U . . .
C24 C -0.1258(2) 0.6993(2) 0.17520(19) 0.0240(5) Uani 1 1 d . . . . .
C25 C 0.2588(3) 0.7383(2) 0.7028(2) 0.0235(4) Uani 1 1 d . . . . .
C26 C 0.3666(3) 0.7285(3) 0.9171(2) 0.0427(7) Uani 1 1 d . . . . .
H26A H 0.4429 0.7920 0.9218 0.051 Uiso 1 1 calc R U . . .
H26B H 0.4296 0.6616 0.9046 0.051 Uiso 1 1 calc R U . . .
C27 C 0.2989(5) 0.7193(3) 1.0337(2) 0.0506(8) Uani 1 1 d . . . . .
H27A H 0.2408 0.7871 1.0467 0.076 Uiso 1 1 calc R U . . .
H27B H 0.3913 0.7070 1.1036 0.076 Uiso 1 1 calc R U . . .
H27C H 0.2205 0.6579 1.0266 0.076 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.208(3) . ?
O2 C9 1.200(3) . ?
O3 C25 1.207(3) . ?
O4 C25 1.338(3) . ?
O4 C26 1.456(3) . ?
N1 C1 1.399(2) . ?
N1 C9 1.418(3) . ?
N1 C8 1.437(3) . ?
C1 C2 1.524(3) . ?
C2 C3 1.508(3) . ?
C2 C11 1.515(3) . ?
C2 C14 1.587(3) . ?
C3 C4 1.384(3) . ?
C3 C8 1.393(3) . ?
C4 C5 1.393(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(3) . ?
C7 H7 0.9500 . ?
C9 C10 1.500(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.330(3) . ?
C11 C25 1.479(3) . ?
C12 C13 1.497(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.547(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.521(3) . ?
C14 H14 1.0000 . ?
C15 C16 1.364(3) . ?
C15 C24 1.441(3) . ?
C16 C17 1.415(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.357(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.405(5) . ?
C18 H18 0.9500 . ?
C19 C24 1.432(3) . ?
C19 C20 1.434(4) . ?
C20 C21 1.351(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.415(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.374(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.415(4) . ?
C23 H23 0.9500 . ?
C26 C27 1.506(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
C25 O4 C26 115.62(19) . . ?
C1 N1 C9 125.73(18) . . ?
C1 N1 C8 109.40(16) . . ?
C9 N1 C8 124.64(18) . . ?
O1 C1 N1 126.14(19) . . ?
O1 C1 C2 125.04(18) . . ?
N1 C1 C2 108.81(17) . . ?
C3 C2 C11 114.62(17) . . ?
C3 C2 C1 102.47(15) . . ?
C11 C2 C1 112.38(16) . . ?
C3 C2 C14 117.49(16) . . ?
C11 C2 C14 101.11(15) . . ?
C1 C2 C14 109.06(16) . . ?
C4 C3 C8 120.6(2) . . ?
C4 C3 C2 129.79(19) . . ?
C8 C3 C2 109.63(18) . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 121.9(2) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C8 C7 C6 117.4(2) . . ?
C8 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
C7 C8 C3 121.3(2) . . ?
C7 C8 N1 129.30(19) . . ?
C3 C8 N1 109.37(18) . . ?
O2 C9 N1 119.5(2) . . ?
O2 C9 C10 122.8(2) . . ?
N1 C9 C10 117.71(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C25 127.78(19) . . ?
C12 C11 C2 112.22(18) . . ?
C25 C11 C2 119.94(17) . . ?
C11 C12 C13 112.46(17) . . ?
C11 C12 H12 123.8 . . ?
C13 C12 H12 123.8 . . ?
C12 C13 C14 102.87(16) . . ?
C12 C13 H13A 111.2 . . ?
C14 C13 H13A 111.2 . . ?
C12 C13 H13B 111.2 . . ?
C14 C13 H13B 111.2 . . ?
H13A C13 H13B 109.1 . . ?
C15 C14 C13 116.65(17) . . ?
C15 C14 C2 115.32(15) . . ?
C13 C14 C2 104.30(15) . . ?
C15 C14 H14 106.6 . . ?
C13 C14 H14 106.6 . . ?
C2 C14 H14 106.6 . . ?
C16 C15 C24 119.3(2) . . ?
C16 C15 C14 120.6(2) . . ?
C24 C15 C14 120.1(2) . . ?
C15 C16 C17 121.8(2) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C18 C17 C16 119.8(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 121.3(2) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C24 119.5(2) . . ?
C18 C19 C20 121.9(2) . . ?
C24 C19 C20 118.6(3) . . ?
C21 C20 C19 121.9(2) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 C21 C22 119.8(3) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C23 C22 C21 120.1(3) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 122.1(2) . . ?
C22 C23 H23 119.0 . . ?
C24 C23 H23 119.0 . . ?
C23 C24 C19 117.6(2) . . ?
C23 C24 C15 124.0(2) . . ?
C19 C24 C15 118.4(2) . . ?
O3 C25 O4 124.75(19) . . ?
O3 C25 C11 123.3(2) . . ?
O4 C25 C11 111.96(18) . . ?
O4 C26 C27 107.2(2) . . ?
O4 C26 H26A 110.3 . . ?
C27 C26 H26A 110.3 . . ?
O4 C26 H26B 110.3 . . ?
C27 C26 H26B 110.3 . . ?
H26A C26 H26B 108.5 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 O1 -0.9(3) . . . . ?
C8 N1 C1 O1 -175.6(2) . . . . ?
C9 N1 C1 C2 179.92(18) . . . . ?
C8 N1 C1 C2 5.2(2) . . . . ?
O1 C1 C2 C3 175.1(2) . . . . ?
N1 C1 C2 C3 -5.71(19) . . . . ?
O1 C1 C2 C11 51.6(3) . . . . ?
N1 C1 C2 C11 -129.23(18) . . . . ?
O1 C1 C2 C14 -59.7(3) . . . . ?
N1 C1 C2 C14 119.50(17) . . . . ?
C11 C2 C3 C4 -54.4(3) . . . . ?
C1 C2 C3 C4 -176.4(2) . . . . ?
C14 C2 C3 C4 64.1(3) . . . . ?
C11 C2 C3 C8 126.24(19) . . . . ?
C1 C2 C3 C8 4.2(2) . . . . ?
C14 C2 C3 C8 -115.25(19) . . . . ?
C8 C3 C4 C5 1.3(3) . . . . ?
C2 C3 C4 C5 -178.00(19) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C6 C7 C8 C3 0.3(3) . . . . ?
C6 C7 C8 N1 179.58(19) . . . . ?
C4 C3 C8 C7 -1.4(3) . . . . ?
C2 C3 C8 C7 178.05(18) . . . . ?
C4 C3 C8 N1 179.23(18) . . . . ?
C2 C3 C8 N1 -1.3(2) . . . . ?
C1 N1 C8 C7 178.2(2) . . . . ?
C9 N1 C8 C7 3.4(4) . . . . ?
C1 N1 C8 C3 -2.5(2) . . . . ?
C9 N1 C8 C3 -177.25(17) . . . . ?
C1 N1 C9 O2 -162.7(2) . . . . ?
C8 N1 C9 O2 11.2(3) . . . . ?
C1 N1 C9 C10 19.1(3) . . . . ?
C8 N1 C9 C10 -167.03(19) . . . . ?
C3 C2 C11 C12 110.6(2) . . . . ?
C1 C2 C11 C12 -132.9(2) . . . . ?
C14 C2 C11 C12 -16.8(2) . . . . ?
C3 C2 C11 C25 -66.6(2) . . . . ?
C1 C2 C11 C25 49.9(3) . . . . ?
C14 C2 C11 C25 166.03(19) . . . . ?
C25 C11 C12 C13 178.0(2) . . . . ?
C2 C11 C12 C13 1.0(3) . . . . ?
C11 C12 C13 C14 15.7(2) . . . . ?
C12 C13 C14 C15 -153.29(18) . . . . ?
C12 C13 C14 C2 -24.8(2) . . . . ?
C3 C2 C14 C15 28.8(3) . . . . ?
C11 C2 C14 C15 154.31(18) . . . . ?
C1 C2 C14 C15 -87.1(2) . . . . ?
C3 C2 C14 C13 -100.4(2) . . . . ?
C11 C2 C14 C13 25.06(19) . . . . ?
C1 C2 C14 C13 143.64(17) . . . . ?
C13 C14 C15 C16 37.7(3) . . . . ?
C2 C14 C15 C16 -85.2(2) . . . . ?
C13 C14 C15 C24 -141.79(19) . . . . ?
C2 C14 C15 C24 95.3(2) . . . . ?
C24 C15 C16 C17 0.1(3) . . . . ?
C14 C15 C16 C17 -179.39(19) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C19 -0.3(4) . . . . ?
C17 C18 C19 C24 -0.4(4) . . . . ?
C17 C18 C19 C20 179.1(2) . . . . ?
C18 C19 C20 C21 179.8(3) . . . . ?
C24 C19 C20 C21 -0.7(4) . . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
C20 C21 C22 C23 0.2(4) . . . . ?
C21 C22 C23 C24 0.1(4) . . . . ?
C22 C23 C24 C19 -0.6(3) . . . . ?
C22 C23 C24 C15 178.7(2) . . . . ?
C18 C19 C24 C23 -179.5(2) . . . . ?
C20 C19 C24 C23 0.9(3) . . . . ?
C18 C19 C24 C15 1.1(3) . . . . ?
C20 C19 C24 C15 -178.46(19) . . . . ?
C16 C15 C24 C23 179.7(2) . . . . ?
C14 C15 C24 C23 -0.7(3) . . . . ?
C16 C15 C24 C19 -0.9(3) . . . . ?
C14 C15 C24 C19 178.63(17) . . . . ?
C26 O4 C25 O3 0.9(4) . . . . ?
C26 O4 C25 C11 -179.8(2) . . . . ?
C12 C11 C25 O3 -174.3(2) . . . . ?
C2 C11 C25 O3 2.5(3) . . . . ?
C12 C11 C25 O4 6.5(3) . . . . ?
C2 C11 C25 O4 -176.8(2) . . . . ?
C25 O4 C26 C27 -171.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 O2 0.95 2.34 2.874(3) 115.4 .
C27 H27B O2 0.98 2.61 3.559(3) 162.4 1_556

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.057

_shelxl_version_number           2014-3



