# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc1ywzkc
_database_code_depnum_ccdc_archive 'CCDC 1814354'
_audit_update_record             
;
2018-01-02 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 N O3, C2 H3 N'
_chemical_formula_sum            'C26 H24 N2 O3'
_chemical_formula_weight         412.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        P-1
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0151(4)
_cell_length_b                   11.4152(5)
_cell_length_c                   12.7980(6)
_cell_angle_alpha                89.432(3)
_cell_angle_beta                 71.763(3)
_cell_angle_gamma                86.136(3)
_cell_volume                     1109.52(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    111
_cell_measurement_theta_min      1.675
_cell_measurement_theta_max      28.378

_exptl_crystal_description       square
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             436.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17926
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.675
_diffrn_reflns_theta_max         28.378
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5535
_reflns_number_gt                2545
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Kappa Apex'
_computing_cell_refinement       'Bruker Kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.1827P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0085(12)
_refine_ls_number_reflns         5535
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1632
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.2979
_refine_ls_wR_factor_gt          0.2155
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_restrained_S_all      0.950
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.022

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 0.2060(3) 0.65127(18) 0.65507(16) 0.0591(6) Uani 1 1 d . . . . .
O3 O 0.4290(3) 0.50240(17) 0.35050(16) 0.0566(6) Uani 1 1 d . . . . .
O2 O 0.3805(3) 0.79509(19) 0.61620(17) 0.0662(6) Uani 1 1 d . . . . .
N1 N 0.5743(3) 0.6931(2) 0.28310(19) 0.0516(6) Uani 1 1 d . . . . .
C8 C 0.3978(3) 0.6680(2) 0.4667(2) 0.0448(7) Uani 1 1 d . . . . .
H8 H 0.2900 0.7012 0.4538 0.054 Uiso 1 1 calc R U . . .
C1 C 0.2282(3) 0.4920(2) 0.5282(2) 0.0456(6) Uani 1 1 d . . . . .
C9 C 0.3334(4) 0.7107(3) 0.5789(2) 0.0506(7) Uani 1 1 d . . . . .
C19 C 0.3441(4) 0.9693(2) 0.2931(2) 0.0516(7) Uani 1 1 d . . . . .
C7 C 0.3591(4) 0.5516(2) 0.4409(2) 0.0454(7) Uani 1 1 d . . . . .
C10 C 0.4997(4) 0.7388(2) 0.3826(2) 0.0467(7) Uani 1 1 d . . . . .
C6 C 0.1537(4) 0.5454(3) 0.6298(2) 0.0519(7) Uani 1 1 d . . . . .
C12 C 0.5310(4) 0.9372(2) 0.2942(2) 0.0530(8) Uani 1 1 d . . . . .
H12 H 0.5848 1.0107 0.2991 0.064 Uiso 1 1 calc R U . . .
C11 C 0.5304(4) 0.8653(2) 0.3959(2) 0.0521(7) Uani 1 1 d . . . . .
H11A H 0.6424 0.8700 0.4092 0.063 Uiso 1 1 calc R U . . .
H11B H 0.4387 0.8987 0.4594 0.063 Uiso 1 1 calc R U . . .
C14 C 0.6631(4) 0.7572(3) 0.1886(2) 0.0553(8) Uani 1 1 d . . . . .
C2 C 0.1728(4) 0.3824(3) 0.5098(3) 0.0548(8) Uani 1 1 d . . . . .
H2 H 0.2226 0.3448 0.4419 0.066 Uiso 1 1 calc R U . . .
C13 C 0.6435(4) 0.8741(3) 0.1912(2) 0.0560(8) Uani 1 1 d . . . . .
C5 C 0.0227(4) 0.4939(3) 0.7116(3) 0.0655(9) Uani 1 1 d . . . . .
H5 H -0.0290 0.5317 0.7791 0.079 Uiso 1 1 calc R U . . .
C24 C 0.2552(4) 0.9004(3) 0.2443(3) 0.0626(9) Uani 1 1 d . . . . .
H24 H 0.3127 0.8324 0.2068 0.075 Uiso 1 1 calc R U . . .
C23 C 0.0832(5) 0.9288(3) 0.2490(3) 0.0717(10) Uani 1 1 d . . . . .
H23 H 0.0260 0.8801 0.2155 0.086 Uiso 1 1 calc R U . . .
C4 C -0.0292(5) 0.3874(3) 0.6920(3) 0.0703(10) Uani 1 1 d . . . . .
H4 H -0.1162 0.3524 0.7469 0.084 Uiso 1 1 calc R U . . .
C3 C 0.0456(4) 0.3302(3) 0.5912(3) 0.0648(9) Uani 1 1 d . . . . .
H3 H 0.0099 0.2572 0.5790 0.078 Uiso 1 1 calc R U . . .
C22 C -0.0026(5) 1.0279(4) 0.3026(3) 0.0797(11) Uani 1 1 d . . . . .
H22 H -0.1186 1.0478 0.3059 0.096 Uiso 1 1 calc R U . . .
C20 C 0.2560(5) 1.0699(3) 0.3463(3) 0.0803(11) Uani 1 1 d . . . . .
H2O H 0.3131 1.1195 0.3790 0.096 Uiso 1 1 calc R U . . .
C21 C 0.0825(6) 1.0981(4) 0.3516(4) 0.1020(15) Uani 1 1 d . . . . .
H21 H 0.0236 1.1657 0.3890 0.122 Uiso 1 1 calc R U . . .
C26 C 0.6313(8) 0.3426(6) 0.0419(5) 0.1234(19) Uani 1 1 d . . . . .
C25 C 0.5535(11) 0.3142(6) 0.1510(4) 0.170(3) Uani 1 1 d . . . . .
H25B H 0.5068 0.2384 0.1549 0.255 Uiso 1 1 calc R U . . .
H25A H 0.4600 0.3720 0.1849 0.255 Uiso 1 1 calc R U . . .
H25C H 0.6399 0.3124 0.1888 0.255 Uiso 1 1 calc R U . . .
N2 N 0.6891(10) 0.3661(8) -0.0437(5) 0.221(4) Uani 1 1 d . . . . .
C15 C 0.7657(5) 0.6833(3) 0.0918(3) 0.0768(10) Uani 1 1 d . . . . .
H15A H 0.6885 0.6304 0.0740 0.092 Uiso 1 1 calc R U . . .
H15B H 0.8576 0.6361 0.1102 0.092 Uiso 1 1 calc R U . . .
C18 C 0.7234(5) 0.9435(3) 0.0900(3) 0.0843(12) Uani 1 1 d . . . . .
H18A H 0.6315 0.9933 0.0742 0.101 Uiso 1 1 calc R U . . .
H18B H 0.8071 0.9940 0.1038 0.101 Uiso 1 1 calc R U . . .
C16 C 0.8469(9) 0.7558(5) -0.0060(4) 0.143(2) Uani 1 1 d . . . . .
H16A H 0.9735 0.7424 -0.0235 0.172 Uiso 1 1 calc R U . . .
H16B H 0.8162 0.7238 -0.0670 0.172 Uiso 1 1 calc R U . . .
C17 C 0.8126(16) 0.8693(6) -0.0055(5) 0.264(6) Uani 1 1 d . . . . .
H17A H 0.7455 0.8829 -0.0563 0.317 Uiso 1 1 calc R U . . .
H17B H 0.9251 0.9022 -0.0394 0.317 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 C6 1.380(4) . ?
O1 C9 1.382(4) . ?
O3 C7 1.238(3) . ?
O2 C9 1.212(3) . ?
N1 C10 1.321(4) . ?
N1 C14 1.421(4) . ?
C8 C10 1.414(4) . ?
C8 C9 1.442(4) . ?
C8 C7 1.449(4) . ?
C8 H8 0.9800 . ?
C1 C6 1.377(4) . ?
C1 C2 1.402(4) . ?
C1 C7 1.469(4) . ?
C19 C20 1.374(5) . ?
C19 C24 1.372(4) . ?
C19 C12 1.522(4) . ?
C10 C11 1.501(4) . ?
C6 C5 1.388(4) . ?
C12 C13 1.502(4) . ?
C12 C11 1.531(4) . ?
C12 H12 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C14 C13 1.332(4) . ?
C14 C15 1.488(5) . ?
C2 C3 1.373(4) . ?
C2 H2 0.9300 . ?
C13 C18 1.498(4) . ?
C5 C4 1.361(5) . ?
C5 H5 0.9300 . ?
C24 C23 1.378(5) . ?
C24 H24 0.9300 . ?
C23 C22 1.356(5) . ?
C23 H23 0.9300 . ?
C4 C3 1.389(5) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C22 C21 1.360(6) . ?
C22 H22 0.9300 . ?
C20 C21 1.387(5) . ?
C20 H2O 0.9300 . ?
C21 H21 0.9300 . ?
C26 N2 1.086(7) . ?
C26 C25 1.385(8) . ?
C25 H25B 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25C 0.9600 . ?
C15 C16 1.489(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 C17 1.454(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C16 C17 1.306(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 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
C6 O1 C9 121.7(2) . . ?
C10 N1 C14 124.9(3) . . ?
C10 C8 C9 120.2(3) . . ?
C10 C8 C7 120.2(2) . . ?
C9 C8 C7 119.6(2) . . ?
C10 C8 H8 90.4 . . ?
C9 C8 H8 90.2 . . ?
C7 C8 H8 90.1 . . ?
C6 C1 C2 118.6(3) . . ?
C6 C1 C7 120.0(3) . . ?
C2 C1 C7 121.4(3) . . ?
O2 C9 O1 114.3(3) . . ?
O2 C9 C8 126.8(3) . . ?
O1 C9 C8 118.9(3) . . ?
C20 C19 C24 117.5(3) . . ?
C20 C19 C12 119.3(3) . . ?
C24 C19 C12 123.2(3) . . ?
O3 C7 C8 123.4(2) . . ?
O3 C7 C1 119.9(2) . . ?
C8 C7 C1 116.7(2) . . ?
N1 C10 C8 119.1(3) . . ?
N1 C10 C11 115.7(3) . . ?
C8 C10 C11 125.2(3) . . ?
O1 C6 C1 121.8(3) . . ?
O1 C6 C5 117.1(3) . . ?
C1 C6 C5 121.1(3) . . ?
C13 C12 C19 113.0(2) . . ?
C13 C12 C11 110.5(2) . . ?
C19 C12 C11 110.9(2) . . ?
C13 C12 H12 107.4 . . ?
C19 C12 H12 107.4 . . ?
C11 C12 H12 107.4 . . ?
C10 C11 C12 112.1(2) . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C13 C14 N1 119.5(3) . . ?
C13 C14 C15 125.8(3) . . ?
N1 C14 C15 114.6(3) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.8 . . ?
C14 C13 C18 120.6(3) . . ?
C14 C13 C12 120.0(3) . . ?
C18 C13 C12 119.3(3) . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.4 . . ?
C19 C24 C23 122.0(3) . . ?
C19 C24 H24 119.0 . . ?
C23 C24 H24 119.0 . . ?
C22 C23 C24 119.9(3) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.1 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.3 . . ?
C23 C22 C21 119.4(3) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H2O 119.7 . . ?
C21 C20 H2O 119.8 . . ?
C22 C21 C20 120.8(4) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
N2 C26 C25 178.5(8) . . ?
C26 C25 H25B 109.5 . . ?
C26 C25 H25A 109.4 . . ?
H25B C25 H25A 109.5 . . ?
C26 C25 H25C 109.6 . . ?
H25B C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
C14 C15 C16 111.8(3) . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15B 109.2 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 107.9 . . ?
C17 C18 C13 112.6(4) . . ?
C17 C18 H18A 109.4 . . ?
C13 C18 H18A 108.9 . . ?
C17 C18 H18B 108.8 . . ?
C13 C18 H18B 109.2 . . ?
H18A C18 H18B 107.8 . . ?
C17 C16 C15 121.6(5) . . ?
C17 C16 H16A 106.3 . . ?
C15 C16 H16A 106.9 . . ?
C17 C16 H16B 107.4 . . ?
C15 C16 H16B 107.1 . . ?
H16A C16 H16B 106.8 . . ?
C16 C17 C18 126.7(5) . . ?
C16 C17 H17A 105.1 . . ?
C18 C17 H17A 105.3 . . ?
C16 C17 H17B 106.3 . . ?
C18 C17 H17B 105.8 . . ?
H17A C17 H17B 106.1 . . ?

_refine_diff_density_max         0.461
_refine_diff_density_min         -0.817
_refine_diff_density_rms         0.144

####################################################################### 
# 
# 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_ups3238na_mw_m1_0m
_database_code_depnum_ccdc_archive 'CCDC 1816147'
_audit_update_record             
;
2018-01-10 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H24 O5'
_chemical_formula_sum            'C25 H24 O5'
_chemical_formula_weight         404.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        P-1
_space_group_name_Hall           '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7460(3)
_cell_length_b                   11.9902(4)
_cell_length_c                   12.4618(4)
_cell_angle_alpha                70.558(2)
_cell_angle_beta                 75.621(2)
_cell_angle_gamma                79.609(2)
_cell_volume                     1051.15(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    111
_cell_measurement_theta_min      1.77
_cell_measurement_theta_max      28.40

_exptl_crystal_description       square
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428.0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18333
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         28.40
_reflns_number_total             5230
_reflns_number_gt                3082
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Kappa Apex'
_computing_cell_refinement       'Bruker Kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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     
'calc w=1/[σ²(Fo²)+(0.1720P)²+0.1103P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.079(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5230
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0762
_refine_ls_wR_factor_ref         0.2808
_refine_ls_wR_factor_gt          0.2420
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.013
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C6 C 0.2327(3) 0.5096(2) 0.4306(2) 0.0476(6) Uani 1 1 d . . .
C8 C 0.2034(3) 0.6610(2) 0.52955(19) 0.0453(5) Uani 1 1 d . . .
C12 C 0.1821(3) 0.8246(2) 0.75792(18) 0.0465(5) Uani 1 1 d . . .
H12 H 0.2849 0.7724 0.7860 0.056 Uiso 1 1 calc R . .
C7 C 0.2541(3) 0.5442(2) 0.52674(19) 0.0462(5) Uani 1 1 d . . .
C5 C 0.1546(3) 0.5941(2) 0.3451(2) 0.0507(6) Uani 1 1 d . . .
C10 C 0.2217(3) 0.6908(2) 0.63070(19) 0.0476(6) Uani 1 1 d . . .
C20 C 0.0184(3) 0.6830(2) 0.94116(19) 0.0471(5) Uani 1 1 d . . .
H20 H 0.1291 0.6451 0.9569 0.056 Uiso 1 1 calc R . .
C19 C 0.0120(3) 0.7807(2) 0.84334(18) 0.0458(5) Uani 1 1 d . . .
C11 C 0.1811(4) 0.8141(2) 0.63790(19) 0.0525(6) Uani 1 1 d . . .
H11A H 0.0642 0.8461 0.6193 0.063 Uiso 1 1 calc R . .
H11B H 0.2687 0.8626 0.5797 0.063 Uiso 1 1 calc R . .
C4 C 0.1238(4) 0.5659(3) 0.2524(2) 0.0594(7) Uani 1 1 d . . .
H4 H 0.0688 0.6232 0.1962 0.071 Uiso 1 1 calc R . .
C13 C 0.2058(3) 0.9519(2) 0.7471(2) 0.0509(6) Uani 1 1 d . . .
H13 H 0.1162 1.0054 0.7053 0.061 Uiso 1 1 calc R . .
C9 C 0.1290(4) 0.7474(2) 0.4354(2) 0.0551(6) Uani 1 1 d . . .
C2 C 0.2578(4) 0.3666(3) 0.3283(3) 0.0685(8) Uani 1 1 d . . .
H2 H 0.2940 0.2905 0.3216 0.082 Uiso 1 1 calc R . .
C1 C 0.2855(3) 0.3948(2) 0.4208(3) 0.0596(7) Uani 1 1 d . . .
H1 H 0.3396 0.3372 0.4772 0.072 Uiso 1 1 calc R . .
C3 C 0.1750(4) 0.4533(3) 0.2447(3) 0.0672(8) Uani 1 1 d . . .
H3 H 0.1544 0.4341 0.1828 0.081 Uiso 1 1 calc R . .
C21 C -0.1363(4) 0.6407(2) 1.0158(2) 0.0540(6) Uani 1 1 d . . .
H21 H -0.1271 0.5755 1.0812 0.065 Uiso 1 1 calc R . .
C22 C -0.3035(3) 0.6926(3) 0.9958(2) 0.0575(7) Uani 1 1 d . . .
C14 C 0.3891(4) 0.9862(3) 0.6785(2) 0.0650(7) Uani 1 1 d . . .
C24 C -0.1560(4) 0.8353(2) 0.8240(2) 0.0593(7) Uani 1 1 d . . .
H24 H -0.1651 0.9024 0.7603 0.071 Uiso 1 1 calc R . .
C23 C -0.3104(4) 0.7913(3) 0.8983(3) 0.0657(7) Uani 1 1 d . . .
H23 H -0.4214 0.8286 0.8825 0.079 Uiso 1 1 calc R . .
C18 C 0.1800(4) 0.9756(3) 0.8634(2) 0.0643(7) Uani 1 1 d . . .
H18A H 0.0605 0.9589 0.9077 0.077 Uiso 1 1 calc R . .
H18B H 0.2655 0.9220 0.9071 0.077 Uiso 1 1 calc R . .
C16 C 0.3847(6) 1.1349(3) 0.7782(4) 0.1004(13) Uani 1 1 d . . .
H16A H 0.4774 1.0875 0.8192 0.121 Uiso 1 1 calc R . .
H16B H 0.3932 1.2181 0.7662 0.121 Uiso 1 1 calc R . .
C25 C -0.4720(4) 0.6441(3) 1.0734(3) 0.0823(10) Uani 1 1 d . . .
H25A H -0.5452 0.6317 1.0274 0.123 Uiso 1 1 calc R . .
H25B H -0.5367 0.6998 1.1134 0.123 Uiso 1 1 calc R . .
H25C H -0.4419 0.5699 1.1290 0.123 Uiso 1 1 calc R . .
C17 C 0.2042(6) 1.1024(3) 0.8493(4) 0.0909(11) Uani 1 1 d . . .
H17A H 0.1119 1.1559 0.8119 0.109 Uiso 1 1 calc R . .
H17B H 0.1905 1.1120 0.9253 0.109 Uiso 1 1 calc R . .
C15 C 0.4123(7) 1.1129(3) 0.6615(4) 0.1093(14) Uani 1 1 d . . .
H15A H 0.3265 1.1658 0.6176 0.131 Uiso 1 1 calc R . .
H15B H 0.5318 1.1299 0.6174 0.131 Uiso 1 1 calc R . .
O2 O 0.2778(2) 0.60935(16) 0.71107(14) 0.0580(5) Uani 1 1 d . . .
O3 O 0.3211(3) 0.46159(16) 0.60887(15) 0.0590(5) Uani 1 1 d . . .
H3A H 0.3273 0.4898 0.6592 0.089 Uiso 1 1 calc R . .
O5 O 0.1040(3) 0.70882(17) 0.34792(15) 0.0610(5) Uani 1 1 d . . .
O4 O 0.0847(3) 0.85113(19) 0.42432(18) 0.0798(7) Uani 1 1 d . . .
O1 O 0.5081(3) 0.9148(2) 0.6466(2) 0.0892(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
C6 C5 1.382(4) . ?
C6 C1 1.400(4) . ?
C6 C7 1.445(3) . ?
C8 C7 1.395(3) . ?
C8 C9 1.447(3) . ?
C8 C10 1.464(3) . ?
C12 C19 1.525(3) . ?
C12 C13 1.528(4) . ?
C12 C11 1.544(3) . ?
C7 O3 1.304(3) . ?
C5 O5 1.370(3) . ?
C5 C4 1.389(3) . ?
C10 O2 1.248(3) . ?
C10 C11 1.483(4) . ?
C20 C21 1.382(3) . ?
C20 C19 1.385(3) . ?
C19 C24 1.387(3) . ?
C4 C3 1.366(4) . ?
C13 C14 1.513(4) . ?
C13 C18 1.526(3) . ?
C9 O4 1.199(3) . ?
C9 O5 1.383(3) . ?
C2 C1 1.378(4) . ?
C2 C3 1.396(4) . ?
C21 C22 1.376(4) . ?
C22 C23 1.390(4) . ?
C22 C25 1.499(4) . ?
C14 O1 1.225(4) . ?
C14 C15 1.500(5) . ?
C24 C23 1.385(4) . ?
C18 C17 1.512(4) . ?
C16 C17 1.497(6) . ?
C16 C15 1.520(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
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 118.0(2) . . ?
C1 C6 C7 123.2(2) . . ?
C7 C8 C9 119.5(2) . . ?
C7 C8 C10 118.4(2) . . ?
C9 C8 C10 122.1(2) . . ?
C19 C12 C13 113.02(18) . . ?
C19 C12 C11 109.37(19) . . ?
C13 C12 C11 110.33(19) . . ?
O3 C7 C8 122.7(2) . . ?
O3 C7 C6 116.9(2) . . ?
C8 C7 C6 120.3(2) . . ?
O5 C5 C6 121.7(2) . . ?
O5 C5 C4 117.2(2) . . ?
C6 C5 C4 121.1(2) . . ?
O2 C10 C8 118.0(2) . . ?
O2 C10 C11 120.0(2) . . ?
C8 C10 C11 122.0(2) . . ?
C21 C20 C19 121.4(2) . . ?
C20 C19 C24 117.3(2) . . ?
C20 C19 C12 121.6(2) . . ?
C24 C19 C12 121.0(2) . . ?
C10 C11 C12 114.11(19) . . ?
C3 C4 C5 119.3(3) . . ?
C14 C13 C18 107.1(2) . . ?
C14 C13 C12 112.0(2) . . ?
C18 C13 C12 114.1(2) . . ?
O4 C9 O5 115.1(2) . . ?
O4 C9 C8 126.9(2) . . ?
O5 C9 C8 118.0(2) . . ?
C1 C2 C3 119.4(3) . . ?
C2 C1 C6 120.5(3) . . ?
C4 C3 C2 120.9(2) . . ?
C22 C21 C20 121.6(2) . . ?
C21 C22 C23 117.1(2) . . ?
C21 C22 C25 122.0(3) . . ?
C23 C22 C25 120.9(3) . . ?
O1 C14 C15 124.2(3) . . ?
O1 C14 C13 122.7(3) . . ?
C15 C14 C13 113.1(3) . . ?
C23 C24 C19 120.9(2) . . ?
C24 C23 C22 121.6(2) . . ?
C17 C18 C13 112.6(2) . . ?
C17 C16 C15 109.8(3) . . ?
C16 C17 C18 111.6(3) . . ?
C14 C15 C16 110.4(3) . . ?
C5 O5 C9 122.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.40
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.220
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.137
