# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_tch71s
_database_code_depnum_ccdc_archive 'CCDC 1495075'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H15 Cl O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         414.82
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.3385(16)
_cell_length_b                   15.072(4)
_cell_length_c                   20.735(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1980.9(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1102
_cell_measurement_theta_min      2.3844
_cell_measurement_theta_max      20.1446
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856

_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            18825
_diffrn_reflns_av_R_equivalents  0.1054
_diffrn_reflns_av_unetI/netI     0.1180
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         29.67
_diffrn_reflns_theta_full        29.67
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28

_refine_special_details          
;
;

_reflns_number_total             5572
_reflns_number_gt                3337
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1321
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.981
_refine_ls_number_reflns         5572
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.335
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 962 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(8)

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3446(7) 0.4235(2) 0.31458(18) 0.0197(9) Uani d . . . 1 . .
C C2 0.6556(6) 0.5078(2) 0.30526(17) 0.0172(8) Uani d . . . 1 . .
C C3 0.8439(7) 0.5491(2) 0.28933(18) 0.0195(8) Uani d . . . 1 . .
H H3 0.9494 0.5189 0.2653 0.023 Uiso calc U . R 1 . .
C C4 0.8739(7) 0.6366(3) 0.30979(19) 0.0240(9) Uani d . . . 1 . .
H H4 1.0026 0.6661 0.3001 0.029 Uiso calc U . R 1 . .
C C5 0.7180(7) 0.6812(3) 0.3442(2) 0.0275(10) Uani d . . . 1 . .
H H5 0.7423 0.7405 0.3578 0.033 Uiso calc U . R 1 . .
C C6 0.5257(7) 0.6399(3) 0.3590(2) 0.0261(10) Uani d . . . 1 . .
H H6 0.4177 0.6698 0.3823 0.031 Uiso calc U . R 1 . .
C C7 0.5016(7) 0.5535(3) 0.33800(19) 0.0203(9) Uani d . . . 1 . .
C C8 0.5717(6) 0.4156(2) 0.29056(19) 0.0169(8) Uani d . . . 1 . .
C C9 0.5838(6) 0.3978(2) 0.21883(19) 0.0164(8) Uani d . . . 1 . .
C C10 0.4187(6) 0.4412(3) 0.17804(19) 0.0186(9) Uani d . . . 1 . .
C C11 0.4170(7) 0.4240(2) 0.10790(19) 0.0190(9) Uani d . . . 1 . .
C C12 0.2521(7) 0.4555(3) 0.07036(19) 0.0230(9) Uani d . . . 1 . .
H H12 0.1406 0.4881 0.0897 0.028 Uiso calc U . R 1 . .
C C13 0.2502(7) 0.4393(3) 0.0039(2) 0.0283(10) Uani d . . . 1 . .
H H13 0.1372 0.4606 -0.0219 0.034 Uiso calc U . R 1 . .
C C14 0.4147(7) 0.3919(3) -0.0242(2) 0.0266(10) Uani d . . . 1 . .
H H14 0.4135 0.3811 -0.0693 0.032 Uiso calc U . R 1 . .
C C15 0.5797(7) 0.3604(3) 0.0129(2) 0.0251(10) Uani d . . . 1 . .
H H15 0.6916 0.3284 -0.0068 0.03 Uiso calc U . R 1 . .
C C16 0.5819(6) 0.3754(2) 0.07909(18) 0.0190(8) Uani d . . . 1 . .
C C17 0.7568(7) 0.3422(2) 0.1195(2) 0.0207(9) Uani d . . . 1 . .
C C18 0.7433(7) 0.3534(2) 0.19025(19) 0.0209(9) Uani d . . . 1 . .
H H18 0.8508 0.3284 0.2165 0.025 Uiso calc U . R 1 . .
C C19 0.6775(7) 0.3406(2) 0.33055(18) 0.0186(9) Uani d . . . 1 . .
H H19A 0.6101 0.2835 0.3191 0.022 Uiso calc U . R 1 . .
H H19B 0.8279 0.3367 0.318 0.022 Uiso calc U . R 1 . .
C C20 0.6647(7) 0.3526(2) 0.40290(18) 0.0179(8) Uani d . . . 1 . .
C C21 0.4947(7) 0.3184(3) 0.4381(2) 0.0250(10) Uani d . . . 1 . .
H H21 0.3833 0.2891 0.4161 0.03 Uiso calc U . R 1 . .
C C22 0.4863(7) 0.3268(3) 0.5049(2) 0.0272(10) Uani d . . . 1 . .
H H22 0.3699 0.3036 0.5284 0.033 Uiso calc U . R 1 . .
C C23 0.6493(7) 0.3691(3) 0.53674(18) 0.0239(9) Uani d . . . 1 . .
C C24 0.8191(7) 0.4043(3) 0.5032(2) 0.0255(10) Uani d . . . 1 . .
H H24 0.9295 0.4337 0.5257 0.031 Uiso calc U . R 1 . .
C C25 0.8261(7) 0.3960(2) 0.43644(18) 0.0218(9) Uani d . . . 1 . .
H H25 0.942 0.4202 0.4133 0.026 Uiso calc U . R 1 . .
Cl Cl1 0.6474(2) 0.37556(8) 0.62102(5) 0.0380(3) Uani d . . . 1 . .
O O1 0.3187(4) 0.50324(17) 0.34745(13) 0.0211(6) Uani d . . . 1 . .
O O2 0.2065(5) 0.36999(18) 0.31258(13) 0.0253(7) Uani d . . . 1 . .
O O3 0.2887(5) 0.49150(19) 0.20347(13) 0.0272(7) Uani d . . . 1 . .
O O4 0.9103(5) 0.30356(18) 0.09631(14) 0.0294(8) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O2 . 1.191(5) ?
C1 O1 . 1.391(4) ?
C1 C8 . 1.527(6) ?
C2 C7 . 1.374(5) ?
C2 C3 . 1.386(6) ?
C2 C8 . 1.519(5) ?
C3 C4 . 1.399(5) ?
C4 C5 . 1.391(6) ?
C5 C6 . 1.403(6) ?
C6 C7 . 1.383(5) ?
C7 O1 . 1.399(5) ?
C8 C9 . 1.513(5) ?
C8 C19 . 1.554(5) ?
C9 C18 . 1.350(5) ?
C9 C10 . 1.496(5) ?
C10 O3 . 1.238(5) ?
C10 C11 . 1.477(5) ?
C11 C12 . 1.387(6) ?
C11 C16 . 1.409(5) ?
C12 C13 . 1.399(6) ?
C13 C14 . 1.392(6) ?
C14 C15 . 1.383(6) ?
C15 C16 . 1.390(5) ?
C16 C17 . 1.476(6) ?
C17 O4 . 1.232(5) ?
C17 C18 . 1.479(6) ?
C19 C20 . 1.513(5) ?
C20 C21 . 1.400(6) ?
C20 C25 . 1.400(6) ?
C21 C22 . 1.392(6) ?
C22 C23 . 1.382(6) ?
C23 C24 . 1.386(6) ?
C23 Cl1 . 1.750(4) ?
C24 C25 . 1.391(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 C1 O1 . . 121.0(4) ?
O2 C1 C8 . . 128.9(3) ?
O1 C1 C8 . . 109.8(3) ?
C7 C2 C3 . . 120.3(3) ?
C7 C2 C8 . . 108.0(3) ?
C3 C2 C8 . . 131.6(4) ?
C2 C3 C4 . . 117.9(4) ?
C5 C4 C3 . . 120.9(4) ?
C4 C5 C6 . . 121.1(4) ?
C7 C6 C5 . . 116.4(4) ?
C2 C7 C6 . . 123.4(4) ?
C2 C7 O1 . . 112.8(3) ?
C6 C7 O1 . . 123.9(4) ?
C9 C8 C2 . . 110.0(3) ?
C9 C8 C1 . . 112.5(3) ?
C2 C8 C1 . . 101.1(3) ?
C9 C8 C19 . . 111.9(3) ?
C2 C8 C19 . . 114.0(3) ?
C1 C8 C19 . . 106.8(3) ?
C18 C9 C10 . . 119.5(4) ?
C18 C9 C8 . . 123.9(4) ?
C10 C9 C8 . . 116.3(3) ?
O3 C10 C11 . . 121.5(4) ?
O3 C10 C9 . . 119.5(4) ?
C11 C10 C9 . . 119.0(3) ?
C12 C11 C16 . . 119.9(4) ?
C12 C11 C10 . . 119.9(4) ?
C16 C11 C10 . . 120.2(4) ?
C11 C12 C13 . . 119.9(4) ?
C14 C13 C12 . . 119.7(4) ?
C15 C14 C13 . . 120.6(4) ?
C14 C15 C16 . . 120.1(4) ?
C15 C16 C11 . . 119.7(4) ?
C15 C16 C17 . . 120.8(4) ?
C11 C16 C17 . . 119.5(4) ?
O4 C17 C16 . . 122.1(4) ?
O4 C17 C18 . . 119.1(4) ?
C16 C17 C18 . . 118.8(4) ?
C9 C18 C17 . . 122.3(4) ?
C20 C19 C8 . . 114.8(3) ?
C21 C20 C25 . . 118.4(4) ?
C21 C20 C19 . . 121.0(4) ?
C25 C20 C19 . . 120.6(4) ?
C22 C21 C20 . . 121.1(4) ?
C23 C22 C21 . . 119.2(4) ?
C22 C23 C24 . . 121.2(4) ?
C22 C23 Cl1 . . 119.8(3) ?
C24 C23 Cl1 . . 119.0(4) ?
C23 C24 C25 . . 119.3(4) ?
C24 C25 C20 . . 120.8(4) ?
C1 O1 C7 . . 107.5(3) ?

####################################################################### 
# 
# 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_20160799
_database_code_depnum_ccdc_archive 'CCDC 1495076'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;
_audit_creation_date             2016-07-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H18 O5'
_chemical_formula_sum            'C26 H18 O5'
_chemical_formula_weight         410.40
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1O1N1
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.9030(6)
_cell_length_b                   6.3446(4)
_cell_length_c                   16.4435(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.703(5)
_cell_angle_gamma                90
_cell_volume                     1029.67(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2520
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.2350
_cell_measurement_theta_min      4.4750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7938
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        67.041
_diffrn_reflns_theta_max         67.041
_diffrn_reflns_theta_min         2.696
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -67.00   -6.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  150.0000 61

#__ type_ start__ end____ width___ exp.time_
  2 omega  -62.00  -36.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega -105.00  -32.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -60.0000 73

#__ type_ start__ end____ width___ exp.time_
  4 omega  -62.00    2.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -19.0000 -120.0000 64

#__ type_ start__ end____ width___ exp.time_
  5 omega  -65.00  -39.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   19.00   46.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  7 omega   41.00   69.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
  8 omega   66.00   96.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
  9 omega   25.00   52.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00  104.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -180.0000 66

#__ type_ start__ end____ width___ exp.time_
 11 omega    0.00   33.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   91.0000  -99.3996 33

#__ type_ start__ end____ width___ exp.time_
 12 omega   58.00  108.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
 13 omega   37.00   63.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega  -32.00   25.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -120.0000 57

#__ type_ start__ end____ width___ exp.time_
 15 omega   61.00  108.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
 16 omega    1.00   79.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000 -180.0000 78

#__ type_ start__ end____ width___ exp.time_
 17 omega   22.00   73.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  150.0000 51

#__ type_ start__ end____ width___ exp.time_
 18 omega   90.00  147.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 57

#__ type_ start__ end____ width___ exp.time_
 19 omega   57.00   91.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
 20 omega  110.00  175.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 65

#__ type_ start__ end____ width___ exp.time_
 21 omega   84.00  110.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega  123.00  173.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 50

#__ type_ start__ end____ width___ exp.time_
 23 omega   79.00  105.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega   79.00  106.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 25 omega   62.00  136.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 74

#__ type_ start__ end____ width___ exp.time_
 26 omega   82.00  112.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 30

#__ type_ start__ end____ width___ exp.time_
 27 omega   88.00  130.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 42

#__ type_ start__ end____ width___ exp.time_
 28 omega  141.00  172.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
 29 omega   79.00  105.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   63.00  125.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  120.0000 62

#__ type_ start__ end____ width___ exp.time_
 31 omega   89.00  122.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 33

#__ type_ start__ end____ width___ exp.time_
 32 omega  121.00  175.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 54

#__ type_ start__ end____ width___ exp.time_
 33 omega   90.00  117.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 34 omega   79.00  105.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 35 omega   39.00   79.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 40

#__ type_ start__ end____ width___ exp.time_
 36 omega   88.00  114.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 37 omega   88.00  119.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
 38 omega   88.00  114.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 39 omega   79.00  105.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 40 omega   64.00   97.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
 41 omega   84.00  109.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 42 omega   39.00   90.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 51

#__ type_ start__ end____ width___ exp.time_
 43 omega   84.00  114.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
 44 omega   88.00  114.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 45 omega  132.00  163.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   75.0000   50.4830 31

#__ type_ start__ end____ width___ exp.time_
 46 omega   80.00  106.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   75.0000   50.4830 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0336330000
_diffrn_orient_matrix_UB_12      0.0477037000
_diffrn_orient_matrix_UB_13      -0.0913223000
_diffrn_orient_matrix_UB_21      0.1493280000
_diffrn_orient_matrix_UB_22      -0.0370177000
_diffrn_orient_matrix_UB_23      -0.0156829000
_diffrn_orient_matrix_UB_31      -0.0303892000
_diffrn_orient_matrix_UB_32      -0.2351797000
_diffrn_orient_matrix_UB_33      -0.0160323000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.654
_reflns_Friedel_fraction_full    0.796
_reflns_Friedel_fraction_max     0.796
_reflns_number_gt                2876
_reflns_number_total             3335
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 990 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3335
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0814P)²+0.0675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1377
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C8(H8), C15(H15), C16(H16), C17(H17), C18(H18),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6852(4) 0.4861(8) -0.0784(2) 0.0590(10) Uani 1 1 d . . . . .
H1 H 0.6936 0.5916 -0.1169 0.071 Uiso 1 1 calc R . . . .
C2 C 0.5962(4) 0.3178(7) -0.0951(2) 0.0592(10) Uani 1 1 d . . . . .
C3 C 0.5869(4) 0.1590(8) -0.0387(2) 0.0650(11) Uani 1 1 d . . . . .
H3 H 0.5288 0.0461 -0.0509 0.078 Uiso 1 1 calc R . . . .
C4 C 0.6614(4) 0.1647(7) 0.0350(2) 0.0589(9) Uani 1 1 d . . . . .
H4 H 0.6539 0.0560 0.0723 0.071 Uiso 1 1 calc R . . . .
C5 C 0.7493(4) 0.3342(6) 0.0545(2) 0.0493(8) Uani 1 1 d . . . . .
C6 C 0.7618(3) 0.4936(7) -0.0027(2) 0.0504(8) Uani 1 1 d . . . . .
C7 C 0.8560(4) 0.6731(7) 0.0174(2) 0.0575(9) Uani 1 1 d . . . . .
C8 C 0.9385(4) 0.6664(6) 0.0957(2) 0.0537(8) Uani 1 1 d . . . . .
H8 H 1.0002 0.7746 0.1077 0.064 Uiso 1 1 calc R . . . .
C9 C 0.9295(3) 0.5130(6) 0.1506(2) 0.0453(7) Uani 1 1 d . . . . .
C10 C 0.8274(4) 0.3417(6) 0.1347(2) 0.0503(8) Uani 1 1 d . . . . .
C11 C 1.0151(3) 0.5052(6) 0.2314(2) 0.0450(7) Uani 1 1 d . . . . .
C12 C 1.0504(4) 0.2784(6) 0.2593(2) 0.0526(8) Uani 1 1 d . . . . .
C13 C 0.9391(3) 0.5820(6) 0.3018(2) 0.0445(7) Uani 1 1 d . . . . .
C14 C 0.9492(4) 0.4270(6) 0.3616(2) 0.0519(9) Uani 1 1 d . . . . .
C15 C 0.8998(4) 0.4551(8) 0.4365(2) 0.0652(11) Uani 1 1 d . . . . .
H15 H 0.9099 0.3522 0.4768 0.078 Uiso 1 1 calc R . . . .
C16 C 0.8342(4) 0.6432(9) 0.4492(3) 0.0711(12) Uani 1 1 d . . . . .
H16 H 0.7981 0.6667 0.4988 0.085 Uiso 1 1 calc R . . . .
C17 C 0.8215(4) 0.7968(8) 0.3895(3) 0.0648(10) Uani 1 1 d . . . . .
H17 H 0.7770 0.9220 0.3997 0.078 Uiso 1 1 calc R . . . .
C18 C 0.8735(4) 0.7680(6) 0.3152(2) 0.0540(8) Uani 1 1 d . . . . .
H18 H 0.8644 0.8716 0.2751 0.065 Uiso 1 1 calc R . . . .
C19 C 1.1524(4) 0.6211(6) 0.2259(2) 0.0527(8) Uani 1 1 d . . . . .
H19A H 1.1948 0.5680 0.1789 0.063 Uiso 1 1 calc R . . . .
H19B H 1.1345 0.7699 0.2170 0.063 Uiso 1 1 calc R . . . .
C20 C 1.2504(4) 0.5967(6) 0.3006(3) 0.0556(9) Uani 1 1 d . . . . .
C21 C 1.2421(4) 0.7202(8) 0.3691(3) 0.0644(11) Uani 1 1 d . . . . .
H21 H 1.1741 0.8212 0.3699 0.077 Uiso 1 1 calc R . . . .
C22 C 1.3333(5) 0.6958(11) 0.4366(3) 0.0861(16) Uani 1 1 d . . . . .
H22 H 1.3251 0.7785 0.4826 0.103 Uiso 1 1 calc R . . . .
C23 C 1.4353(6) 0.5517(12) 0.4364(4) 0.105(2) Uani 1 1 d . . . . .
H23 H 1.4958 0.5343 0.4823 0.126 Uiso 1 1 calc R . . . .
C24 C 1.4473(7) 0.4346(13) 0.3689(5) 0.126(3) Uani 1 1 d . . . . .
H24 H 1.5184 0.3392 0.3675 0.151 Uiso 1 1 calc R . . . .
C25 C 1.3545(6) 0.4552(10) 0.3014(4) 0.0933(18) Uani 1 1 d . . . . .
H25 H 1.3634 0.3711 0.2558 0.112 Uiso 1 1 calc R . . . .
C26 C 0.5118(6) 0.4554(12) -0.2249(3) 0.0944(18) Uani 1 1 d . . . . .
H26A H 0.4764 0.5835 -0.2040 0.142 Uiso 1 1 calc GR . . . .
H26B H 0.4554 0.4108 -0.2720 0.142 Uiso 1 1 calc GR . . . .
H26C H 0.6022 0.4794 -0.2398 0.142 Uiso 1 1 calc GR . . . .
O1 O 0.5138(4) 0.2987(7) -0.1649(2) 0.0882(11) Uani 1 1 d . . . . .
O2 O 0.8666(4) 0.8191(6) -0.02913(19) 0.0820(10) Uani 1 1 d . . . . .
O3 O 0.8083(3) 0.2139(5) 0.18818(18) 0.0741(9) Uani 1 1 d . . . . .
O4 O 1.0178(3) 0.2490(4) 0.33804(16) 0.0589(7) Uani 1 1 d . . . . .
O5 O 1.1077(4) 0.1461(5) 0.2241(2) 0.0719(8) 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
C1 H1 0.9300 . ?
C1 C2 1.398(6) . ?
C1 C6 1.404(5) . ?
C2 C3 1.378(6) . ?
C2 O1 1.359(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.404(5) . ?
C5 C6 1.394(5) . ?
C5 C10 1.473(5) . ?
C6 C7 1.492(6) . ?
C7 C8 1.468(6) . ?
C7 O2 1.212(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.335(5) . ?
C9 C10 1.493(5) . ?
C9 C11 1.518(5) . ?
C10 O3 1.222(4) . ?
C11 C12 1.541(5) . ?
C11 C13 1.512(5) . ?
C11 C19 1.554(5) . ?
C12 O4 1.373(5) . ?
C12 O5 1.189(5) . ?
C13 C14 1.388(5) . ?
C13 C18 1.374(6) . ?
C14 C15 1.373(6) . ?
C14 O4 1.389(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.383(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(6) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.510(6) . ?
C20 C21 1.381(6) . ?
C20 C25 1.367(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.380(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.362(8) . ?
C23 H23 0.9300 . ?
C23 C24 1.350(9) . ?
C24 H24 0.9300 . ?
C24 C25 1.387(8) . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C26 O1 1.399(7) . ?

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
C2 C1 H1 120.4 . . ?
C2 C1 C6 119.1(4) . . ?
C6 C1 H1 120.4 . . ?
C3 C2 C1 120.2(4) . . ?
O1 C2 C1 124.0(4) . . ?
O1 C2 C3 115.8(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.1(4) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(4) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C10 120.0(3) . . ?
C6 C5 C4 119.3(3) . . ?
C6 C5 C10 120.8(3) . . ?
C1 C6 C7 120.3(4) . . ?
C5 C6 C1 120.2(4) . . ?
C5 C6 C7 119.5(3) . . ?
C8 C7 C6 117.7(3) . . ?
O2 C7 C6 121.9(4) . . ?
O2 C7 C8 120.4(4) . . ?
C7 C8 H8 118.3 . . ?
C9 C8 C7 123.4(4) . . ?
C9 C8 H8 118.3 . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 C11 123.5(3) . . ?
C10 C9 C11 116.8(3) . . ?
C5 C10 C9 118.6(3) . . ?
O3 C10 C5 121.4(3) . . ?
O3 C10 C9 120.0(3) . . ?
C9 C11 C12 112.8(3) . . ?
C9 C11 C19 111.2(3) . . ?
C12 C11 C19 106.3(3) . . ?
C13 C11 C9 112.5(3) . . ?
C13 C11 C12 100.9(3) . . ?
C13 C11 C19 112.6(3) . . ?
O4 C12 C11 109.9(3) . . ?
O5 C12 C11 128.3(3) . . ?
O5 C12 O4 121.4(4) . . ?
C14 C13 C11 107.6(3) . . ?
C18 C13 C11 132.2(3) . . ?
C18 C13 C14 120.2(3) . . ?
C13 C14 O4 112.7(3) . . ?
C15 C14 C13 122.2(4) . . ?
C15 C14 O4 125.0(4) . . ?
C14 C15 H15 121.5 . . ?
C14 C15 C16 117.0(4) . . ?
C16 C15 H15 121.5 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.2(4) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.2(4) . . ?
C18 C17 H17 119.4 . . ?
C13 C18 C17 118.2(4) . . ?
C13 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
C11 C19 H19A 108.7 . . ?
C11 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 C11 114.3(3) . . ?
C20 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C21 C20 C19 121.9(4) . . ?
C25 C20 C19 120.6(4) . . ?
C25 C20 C21 117.4(4) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.9(4) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.7(5) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 120.5 . . ?
C24 C23 C22 119.1(5) . . ?
C24 C23 H23 120.5 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.6(5) . . ?
C25 C24 H24 119.7 . . ?
C20 C25 C24 121.3(5) . . ?
C20 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O1 C26 H26A 109.5 . . ?
O1 C26 H26B 109.5 . . ?
O1 C26 H26C 109.5 . . ?
C2 O1 C26 120.3(5) . . ?
C12 O4 C14 108.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 1.5(6) . . . . ?
C1 C2 O1 C26 -1.6(7) . . . . ?
C1 C6 C7 C8 -176.9(3) . . . . ?
C1 C6 C7 O2 2.2(6) . . . . ?
C2 C1 C6 C5 0.4(5) . . . . ?
C2 C1 C6 C7 -179.0(3) . . . . ?
C2 C3 C4 C5 0.1(6) . . . . ?
C3 C2 O1 C26 177.7(5) . . . . ?
C3 C4 C5 C6 -1.4(6) . . . . ?
C3 C4 C5 C10 178.8(4) . . . . ?
C4 C5 C6 C1 1.1(5) . . . . ?
C4 C5 C6 C7 -179.4(4) . . . . ?
C4 C5 C10 C9 174.3(3) . . . . ?
C4 C5 C10 O3 -7.1(6) . . . . ?
C5 C6 C7 C8 3.7(5) . . . . ?
C5 C6 C7 O2 -177.2(4) . . . . ?
C6 C1 C2 C3 -1.7(6) . . . . ?
C6 C1 C2 O1 177.5(4) . . . . ?
C6 C5 C10 C9 -5.5(5) . . . . ?
C6 C5 C10 O3 173.1(4) . . . . ?
C6 C7 C8 C9 -2.6(6) . . . . ?
C7 C8 C9 C10 -2.5(6) . . . . ?
C7 C8 C9 C11 179.7(3) . . . . ?
C8 C9 C10 C5 6.5(5) . . . . ?
C8 C9 C10 O3 -172.0(4) . . . . ?
C8 C9 C11 C12 -146.5(4) . . . . ?
C8 C9 C11 C13 100.2(4) . . . . ?
C8 C9 C11 C19 -27.1(5) . . . . ?
C9 C11 C12 O4 -128.6(3) . . . . ?
C9 C11 C12 O5 57.5(5) . . . . ?
C9 C11 C13 C14 127.0(3) . . . . ?
C9 C11 C13 C18 -56.1(5) . . . . ?
C9 C11 C19 C20 -172.7(3) . . . . ?
C10 C5 C6 C1 -179.0(3) . . . . ?
C10 C5 C6 C7 0.4(5) . . . . ?
C10 C9 C11 C12 35.6(4) . . . . ?
C10 C9 C11 C13 -77.7(4) . . . . ?
C10 C9 C11 C19 154.9(3) . . . . ?
C11 C9 C10 C5 -175.5(3) . . . . ?
C11 C9 C10 O3 6.0(5) . . . . ?
C11 C12 O4 C14 7.0(4) . . . . ?
C11 C13 C14 C15 174.8(4) . . . . ?
C11 C13 C14 O4 -3.0(4) . . . . ?
C11 C13 C18 C17 -175.2(4) . . . . ?
C11 C19 C20 C21 -82.0(5) . . . . ?
C11 C19 C20 C25 100.4(5) . . . . ?
C12 C11 C13 C14 6.6(4) . . . . ?
C12 C11 C13 C18 -176.5(4) . . . . ?
C12 C11 C19 C20 -49.5(4) . . . . ?
C13 C11 C12 O4 -8.4(4) . . . . ?
C13 C11 C12 O5 177.7(4) . . . . ?
C13 C11 C19 C20 60.0(4) . . . . ?
C13 C14 C15 C16 2.3(6) . . . . ?
C13 C14 O4 C12 -2.6(4) . . . . ?
C14 C13 C18 C17 1.4(5) . . . . ?
C14 C15 C16 C17 -1.1(7) . . . . ?
C15 C14 O4 C12 179.7(4) . . . . ?
C15 C16 C17 C18 0.1(7) . . . . ?
C16 C17 C18 C13 -0.2(6) . . . . ?
C18 C13 C14 C15 -2.5(6) . . . . ?
C18 C13 C14 O4 179.6(3) . . . . ?
C19 C11 C12 O4 109.3(3) . . . . ?
C19 C11 C12 O5 -64.6(5) . . . . ?
C19 C11 C13 C14 -106.4(3) . . . . ?
C19 C11 C13 C18 70.6(5) . . . . ?
C19 C20 C21 C22 -179.7(4) . . . . ?
C19 C20 C25 C24 178.5(6) . . . . ?
C20 C21 C22 C23 1.2(9) . . . . ?
C21 C20 C25 C24 0.8(9) . . . . ?
C21 C22 C23 C24 0.9(11) . . . . ?
C22 C23 C24 C25 -2.2(14) . . . . ?
C23 C24 C25 C20 1.3(13) . . . . ?
C25 C20 C21 C22 -2.1(7) . . . . ?
O1 C2 C3 C4 -177.8(4) . . . . ?
O2 C7 C8 C9 178.3(4) . . . . ?
O4 C14 C15 C16 179.9(4) . . . . ?
O5 C12 O4 C14 -178.6(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ly8020x
_database_code_depnum_ccdc_archive 'CCDC 1495077'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;
_audit_creation_date             2016-07-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H20 O4'
_chemical_formula_sum            'C31 H20 O4'
_chemical_formula_weight         456.47
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H11O3
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.1942(8)
_cell_length_b                   6.6554(5)
_cell_length_c                   16.7572(13)
_cell_angle_alpha                90
_cell_angle_beta                 108.366(8)
_cell_angle_gamma                90
_cell_volume                     1184.85(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2881
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.7220
_cell_measurement_theta_min      4.1320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10438
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.765
_diffrn_reflns_theta_min         4.161
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00  36.00   1.00    1.00    --  -33.50  25.00 -64.00   84
  2  ω   -107.00 -74.00   1.00    1.00    --  -33.50 178.00 120.00   33
  3  ω    -48.00  21.00   1.00    1.00    --  -33.50  37.00  30.00   69
  4  ω     18.00  46.00   1.00    1.00    --   36.55  57.00  60.00   28
  5  ω      0.00  57.00   1.00    1.00    --   36.55 -99.00  60.00   57
  6  ω     25.00  51.00   1.00    1.00    --   36.55  37.00   0.00   26
  7  ω     73.00  99.00   1.00    1.00    --   36.55  37.00   0.00   26
  8  ω    -23.00  40.00   1.00    1.00    --   36.55 -57.00-180.00   63
  9  ω     37.00  63.00   1.00    1.00    --   36.55  57.00 120.00   26
 10  ω     43.00  69.00   1.00    1.00    --   36.55  19.00 150.00   26
 11  ω     33.00  70.00   1.00    1.00    --   36.55  57.00  90.00   37
 12  ω     63.00 102.00   1.00    1.00    --   36.55  37.00  30.00   39
 13  ω     72.00  98.00   1.00    1.00    --   36.55  57.00  60.00   26
 14  ω     18.00  66.00   1.00    1.00    --   36.55  57.00 -30.00   48
 15  ω     18.00  44.00   1.00    1.00    --   36.55  77.00  60.00   26
 16  ω      9.00 103.00   1.00    1.00    --   36.55  77.00 120.00   94
 17  ω     -3.00  34.00   1.00    1.00    --   36.55 -99.00 -30.00   37
 18  ω    114.00 175.00   1.00    5.00    --  108.00  77.00 -30.00   61
 19  ω     79.00 105.00   1.00    5.00    --  108.00  77.00 -30.00   26
 20  ω     79.00 105.00   1.00    5.00    --  108.00  77.00  30.00   26
 21  ω     38.00  81.00   1.00    5.00    --  108.00 -94.00-120.00   43
 22  ω     82.00 114.00   1.00    5.00    --  108.00  30.00  60.00   32
 23  ω     84.00 110.00   1.00    5.00    --  108.00  30.00  30.00   26
 24  ω    135.00 164.00   1.00    5.00    --  108.00  61.00   0.00   29
 25  ω     77.00 103.00   1.00    5.00    --  108.00 -94.00 -60.00   26
 26  ω     90.00 116.00   1.00    5.00    --  108.00  61.00 -30.00   26
 27  ω     79.00 105.00   1.00    5.00    --  108.00  77.00   0.00   26
 28  ω     83.00 109.00   1.00    5.00    --  108.00  30.00  90.00   26
 29  ω     82.00 155.00   1.00    5.00    --  108.00  30.00 120.00   73
 30  ω     89.00 114.00   1.00    5.00    --  108.00  61.00  60.00   25
 31  ω    122.00 166.00   1.00    5.00    --  108.00  77.00  60.00   44
 32  ω     81.00 107.00   1.00    5.00    --  108.00  77.00 -60.00   26
 33  ω     89.00 161.00   1.00    5.00    --  108.00  61.00 -60.00   72
 34  ω     79.00 105.00   1.00    5.00    --  108.00  77.00  60.00   26
 35  ω     82.00 114.00   1.00    5.00    --  108.00  30.00   0.00   32
 36  ω     80.00 107.00   1.00    5.00    --  108.00  77.00  90.00   27
 37  ω    101.00 172.00   1.00    5.00    --  108.00 111.00 120.00   71
 38  ω     89.00 124.00   1.00    5.00    --  108.00  61.00  30.00   35
 39  ω     88.00 176.00   1.00    5.00    --  108.00  61.00  90.00   88
 40  ω    113.00 176.00   1.00    5.00    --  108.00  77.00  30.00   63
 41  ω     91.00 117.00   1.00    5.00    --  108.00  45.00   0.00   26
 42  ω     39.00  98.00   1.00    5.00    --  108.00 -45.00  30.00   59
 43  ω     89.00 129.00   1.00    5.00    --  108.00  61.00   0.00   40
 44  ω     48.00 115.00   1.00    5.00    --  108.00-111.00-150.00   67
 45  ω    -66.00 -40.00   1.00    1.00    --  -33.50 -77.00  60.00   26
 46  ω     17.00  43.00   1.00    1.00    --   36.47  77.00   0.00   26
 47  ω     82.00 107.00   1.00    1.00    --   36.47  37.00 120.00   25
 48  ω     88.00 114.00   1.00    5.00    --  108.00  61.00  30.00   26
 49  ω     88.00 113.00   1.00    5.00    --  108.00  45.00  30.00   25
 50  ω     88.00 113.00   1.00    5.00    --  108.00  45.00 -30.00   25
 51  ω     80.00 105.00   1.00    1.00    --   36.47  57.00-120.00   25
 52  ω     84.00 109.00   1.00    5.00    --  108.00 -94.00 -30.00   25
 53  ω     37.00  62.00   1.00    5.00    --  108.00 -30.00 120.00   25
 54  ω     37.00  62.00   1.00    5.00    --  108.00 -30.00-180.00   25
 55  ω     63.00  89.00   1.00    5.00    --  108.00 -45.00 -60.00   26
 56  ω     53.00  79.00   1.00    5.00    --  108.00 -30.00  60.00   26
 57  ω    112.00 137.00   1.00    5.00    --  108.00 -77.00 -60.00   25
 58  ω     57.00  82.00   1.00    1.00    --   36.47 178.00-180.00   25
 59  ω      9.00  35.00   1.00    1.00    --   36.47  77.00  90.00   26
 60  ω     18.00  44.00   1.00    1.00    --   36.47  77.00   0.00   26
 61  ω     74.00 100.00   1.00    1.00    --   36.47 178.00-120.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1259917000
_diffrn_orient_matrix_UB_12      -0.0700729000
_diffrn_orient_matrix_UB_13      -0.0626438000
_diffrn_orient_matrix_UB_21      0.0666907000
_diffrn_orient_matrix_UB_22      -0.0464386000
_diffrn_orient_matrix_UB_23      -0.0654945000
_diffrn_orient_matrix_UB_31      0.0266018000
_diffrn_orient_matrix_UB_32      -0.2157185000
_diffrn_orient_matrix_UB_33      0.0344775000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.850
_reflns_Friedel_fraction_max     0.821
_reflns_number_gt                3321
_reflns_number_total             4140
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1095 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(19)
_refine_ls_extinction_coef       0.0014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4140
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0996
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C18(H18), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2516(3) 0.0977(5) 0.8308(2) 0.0564(8) Uani 1 1 d . . . . .
H1 H 0.2295 0.0033 0.7877 0.068 Uiso 1 1 calc R . . . .
C2 C 0.3430(3) 0.0553(6) 0.9076(3) 0.0703(10) Uani 1 1 d . . . . .
H2 H 0.3825 -0.0694 0.9158 0.084 Uiso 1 1 calc R . . . .
C3 C 0.3758(4) 0.1961(7) 0.9717(3) 0.0744(12) Uani 1 1 d . . . . .
H3 H 0.4367 0.1642 1.0223 0.089 Uiso 1 1 calc R . . . .
C4 C 0.3194(3) 0.3831(6) 0.9616(2) 0.0648(10) Uani 1 1 d . . . . .
H4 H 0.3409 0.4785 1.0043 0.078 Uiso 1 1 calc R . . . .
C5 C 0.2304(3) 0.4214(5) 0.88567(19) 0.0482(7) Uani 1 1 d . . . . .
C6 C 0.1957(2) 0.2832(5) 0.82130(18) 0.0439(6) Uani 1 1 d . . . . .
C7 C 0.0925(3) 0.3748(4) 0.74907(17) 0.0418(6) Uani 1 1 d . . . . .
C8 C 0.0879(3) 0.5894(5) 0.78315(18) 0.0477(7) Uani 1 1 d . . . . .
C9 C -0.0379(3) 0.2738(5) 0.73738(18) 0.0483(7) Uani 1 1 d . . . . .
H9A H -0.1003 0.3373 0.6904 0.058 Uiso 1 1 calc R . . . .
H9B H -0.0328 0.1335 0.7231 0.058 Uiso 1 1 calc R . . . .
C10 C -0.0821(3) 0.2857(5) 0.81361(19) 0.0467(7) Uani 1 1 d . . . . .
C11 C -0.1506(3) 0.4497(5) 0.8260(2) 0.0579(8) Uani 1 1 d . . . . .
H11 H -0.1706 0.5530 0.7866 0.070 Uiso 1 1 calc R . . . .
C12 C -0.1894(4) 0.4604(6) 0.8969(2) 0.0663(10) Uani 1 1 d . . . . .
H12 H -0.2344 0.5719 0.9049 0.080 Uiso 1 1 calc R . . . .
C13 C -0.1625(3) 0.3102(6) 0.9547(2) 0.0634(9) Uani 1 1 d . . . . .
H13 H -0.1888 0.3187 1.0019 0.076 Uiso 1 1 calc R . . . .
C14 C -0.0960(3) 0.1453(6) 0.9428(2) 0.0671(10) Uani 1 1 d . . . . .
H14 H -0.0778 0.0416 0.9820 0.080 Uiso 1 1 calc R . . . .
C15 C -0.0558(3) 0.1333(6) 0.8726(2) 0.0585(8) Uani 1 1 d . . . . .
H15 H -0.0107 0.0214 0.8651 0.070 Uiso 1 1 calc R . . . .
C16 C 0.2253(3) 0.5233(5) 0.66438(18) 0.0454(7) Uani 1 1 d . . . . .
C17 C 0.1244(3) 0.3778(5) 0.66771(17) 0.0431(6) Uani 1 1 d . . . . .
C18 C 0.0717(3) 0.2575(6) 0.6030(2) 0.0562(8) Uani 1 1 d . . . . .
H18 H 0.0124 0.1640 0.6076 0.067 Uiso 1 1 calc R . . . .
C19 C 0.1031(3) 0.2666(7) 0.5248(2) 0.0691(10) Uani 1 1 d . . . . .
C20 C 0.2006(3) 0.4102(6) 0.51806(19) 0.0534(8) Uani 1 1 d . . . . .
C21 C 0.2625(3) 0.5330(5) 0.58604(18) 0.0464(7) Uani 1 1 d . . . . .
C22 C 0.3569(3) 0.6650(5) 0.5792(2) 0.0515(7) Uani 1 1 d . . . . .
C23 C 0.3822(4) 0.6684(7) 0.5023(3) 0.0703(11) Uani 1 1 d . . . . .
H23 H 0.4440 0.7551 0.4964 0.084 Uiso 1 1 calc R . . . .
C24 C 0.3192(4) 0.5490(7) 0.4355(2) 0.0731(12) Uani 1 1 d . . . . .
H24 H 0.3377 0.5570 0.3853 0.088 Uiso 1 1 calc R . . . .
C25 C 0.2291(3) 0.4179(6) 0.4432(2) 0.0640(9) Uani 1 1 d . . . . .
H25 H 0.1873 0.3346 0.3986 0.077 Uiso 1 1 calc R . . . .
C26 C 0.4313(3) 0.8032(5) 0.6472(2) 0.0517(8) Uani 1 1 d . . . . .
C27 C 0.3988(4) 0.9988(7) 0.6474(3) 0.0883(14) Uani 1 1 d . . . . .
H27 H 0.3276 1.0457 0.6061 0.106 Uiso 1 1 calc R . . . .
C28 C 0.4696(4) 1.1314(8) 0.7082(4) 0.0997(17) Uani 1 1 d . . . . .
H28 H 0.4432 1.2638 0.7084 0.120 Uiso 1 1 calc R . . . .
C29 C 0.5760(4) 1.0698(7) 0.7667(3) 0.0750(11) Uani 1 1 d . . . . .
H29 H 0.6244 1.1590 0.8066 0.090 Uiso 1 1 calc R . . . .
C30 C 0.6108(5) 0.8766(8) 0.7661(3) 0.1016(17) Uani 1 1 d . . . . .
H30 H 0.6834 0.8318 0.8068 0.122 Uiso 1 1 calc R . . . .
C31 C 0.5406(5) 0.7428(7) 0.7063(3) 0.0915(15) Uani 1 1 d . . . . .
H31 H 0.5679 0.6109 0.7063 0.110 Uiso 1 1 calc R . . . .
O1 O 0.1648(2) 0.6023(4) 0.86464(13) 0.0541(5) Uani 1 1 d . . . . .
O2 O 0.0228(2) 0.7263(4) 0.74899(15) 0.0617(6) Uani 1 1 d . . . . .
O3 O 0.2739(2) 0.6270(4) 0.72529(14) 0.0665(7) Uani 1 1 d . . . . .
O4 O 0.0508(4) 0.1557(7) 0.4673(2) 0.1341(19) 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
C1 H1 0.9300 . ?
C1 C2 1.397(5) . ?
C1 C6 1.370(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(5) . ?
C5 C6 1.377(4) . ?
C5 O1 1.396(4) . ?
C6 C7 1.514(4) . ?
C7 C8 1.545(4) . ?
C7 C9 1.562(4) . ?
C7 C17 1.515(4) . ?
C8 O1 1.368(4) . ?
C8 O2 1.194(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.511(4) . ?
C10 C11 1.386(4) . ?
C10 C15 1.382(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.391(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.358(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.502(4) . ?
C16 C21 1.498(4) . ?
C16 O3 1.210(4) . ?
C17 C18 1.327(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.462(4) . ?
C19 C20 1.481(5) . ?
C19 O4 1.208(5) . ?
C20 C21 1.396(4) . ?
C20 C25 1.390(4) . ?
C21 C22 1.406(4) . ?
C22 C23 1.403(4) . ?
C22 C26 1.497(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.372(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.370(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.352(6) . ?
C26 C31 1.370(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.391(7) . ?
C28 H28 0.9300 . ?
C28 C29 1.345(7) . ?
C29 H29 0.9300 . ?
C29 C30 1.345(6) . ?
C30 H30 0.9300 . ?
C30 C31 1.385(6) . ?
C31 H31 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 121.2 . . ?
C6 C1 H1 121.2 . . ?
C6 C1 C2 117.7(4) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.1(4) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 121.6 . . ?
C5 C4 C3 116.9(4) . . ?
C5 C4 H4 121.6 . . ?
C4 C5 C6 123.1(3) . . ?
C4 C5 O1 124.4(3) . . ?
C6 C5 O1 112.5(3) . . ?
C1 C6 C5 120.3(3) . . ?
C1 C6 C7 131.4(3) . . ?
C5 C6 C7 108.2(3) . . ?
C6 C7 C8 100.5(2) . . ?
C6 C7 C9 112.0(2) . . ?
C6 C7 C17 112.8(2) . . ?
C8 C7 C9 107.8(2) . . ?
C17 C7 C8 111.4(2) . . ?
C17 C7 C9 111.7(2) . . ?
O1 C8 C7 110.1(3) . . ?
O2 C8 C7 127.9(3) . . ?
O2 C8 O1 121.9(3) . . ?
C7 C9 H9A 108.7 . . ?
C7 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 C7 114.4(2) . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C11 C10 C9 120.8(3) . . ?
C15 C10 C9 120.9(3) . . ?
C15 C10 C11 118.3(3) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.7(3) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C21 C16 C17 118.7(3) . . ?
O3 C16 C17 118.6(2) . . ?
O3 C16 C21 122.7(3) . . ?
C16 C17 C7 115.8(2) . . ?
C18 C17 C7 123.9(3) . . ?
C18 C17 C16 120.3(3) . . ?
C17 C18 H18 118.8 . . ?
C17 C18 C19 122.5(3) . . ?
C19 C18 H18 118.8 . . ?
C18 C19 C20 119.1(3) . . ?
O4 C19 C18 119.8(4) . . ?
O4 C19 C20 121.2(3) . . ?
C21 C20 C19 120.3(3) . . ?
C25 C20 C19 118.5(3) . . ?
C25 C20 C21 121.2(3) . . ?
C20 C21 C16 119.1(3) . . ?
C20 C21 C22 119.4(3) . . ?
C22 C21 C16 121.5(3) . . ?
C21 C22 C26 125.0(3) . . ?
C23 C22 C21 117.4(3) . . ?
C23 C22 C26 117.6(3) . . ?
C22 C23 H23 118.7 . . ?
C24 C23 C22 122.6(4) . . ?
C24 C23 H23 118.7 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.8(3) . . ?
C25 C24 H24 120.1 . . ?
C20 C25 H25 120.2 . . ?
C24 C25 C20 119.6(4) . . ?
C24 C25 H25 120.2 . . ?
C27 C26 C22 120.5(3) . . ?
C27 C26 C31 117.4(4) . . ?
C31 C26 C22 121.8(3) . . ?
C26 C27 H27 119.3 . . ?
C26 C27 C28 121.4(4) . . ?
C28 C27 H27 119.3 . . ?
C27 C28 H28 119.7 . . ?
C29 C28 C27 120.6(5) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 H29 120.7 . . ?
C30 C29 C28 118.6(4) . . ?
C30 C29 H29 120.7 . . ?
C29 C30 H30 119.3 . . ?
C29 C30 C31 121.3(4) . . ?
C31 C30 H30 119.3 . . ?
C26 C31 C30 120.6(4) . . ?
C26 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C8 O1 C5 108.3(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.3(6) . . . . ?
C1 C6 C7 C8 -176.5(3) . . . . ?
C1 C6 C7 C9 69.2(4) . . . . ?
C1 C6 C7 C17 -57.8(4) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
C2 C1 C6 C7 -177.9(3) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C3 C4 C5 O1 -179.7(3) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C4 C5 C6 C7 177.9(3) . . . . ?
C4 C5 O1 C8 177.6(3) . . . . ?
C5 C6 C7 C8 5.0(3) . . . . ?
C5 C6 C7 C9 -109.2(3) . . . . ?
C5 C6 C7 C17 123.8(3) . . . . ?
C6 C1 C2 C3 0.0(5) . . . . ?
C6 C5 O1 C8 -2.6(3) . . . . ?
C6 C7 C8 O1 -6.7(3) . . . . ?
C6 C7 C8 O2 178.2(3) . . . . ?
C6 C7 C9 C10 58.7(4) . . . . ?
C6 C7 C17 C16 -70.8(3) . . . . ?
C6 C7 C17 C18 107.1(4) . . . . ?
C7 C8 O1 C5 5.9(3) . . . . ?
C7 C9 C10 C11 87.8(4) . . . . ?
C7 C9 C10 C15 -92.5(4) . . . . ?
C7 C17 C18 C19 178.9(3) . . . . ?
C8 C7 C9 C10 -51.0(4) . . . . ?
C8 C7 C17 C16 41.4(3) . . . . ?
C8 C7 C17 C18 -140.6(3) . . . . ?
C9 C7 C8 O1 110.7(3) . . . . ?
C9 C7 C8 O2 -64.4(4) . . . . ?
C9 C7 C17 C16 162.0(3) . . . . ?
C9 C7 C17 C18 -20.0(4) . . . . ?
C9 C10 C11 C12 -179.2(3) . . . . ?
C9 C10 C15 C14 179.6(3) . . . . ?
C10 C11 C12 C13 -0.8(6) . . . . ?
C11 C10 C15 C14 -0.6(5) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C12 C13 C14 C15 0.5(6) . . . . ?
C13 C14 C15 C10 -0.2(6) . . . . ?
C15 C10 C11 C12 1.1(5) . . . . ?
C16 C17 C18 C19 -3.2(5) . . . . ?
C16 C21 C22 C23 -177.8(3) . . . . ?
C16 C21 C22 C26 1.5(5) . . . . ?
C17 C7 C8 O1 -126.4(3) . . . . ?
C17 C7 C8 O2 58.5(4) . . . . ?
C17 C7 C9 C10 -173.7(3) . . . . ?
C17 C16 C21 C20 1.4(4) . . . . ?
C17 C16 C21 C22 -179.5(3) . . . . ?
C17 C18 C19 C20 2.1(6) . . . . ?
C17 C18 C19 O4 -178.9(5) . . . . ?
C18 C19 C20 C21 0.8(6) . . . . ?
C18 C19 C20 C25 -179.7(4) . . . . ?
C19 C20 C21 C16 -2.4(5) . . . . ?
C19 C20 C21 C22 178.5(3) . . . . ?
C19 C20 C25 C24 -179.8(3) . . . . ?
C20 C21 C22 C23 1.2(5) . . . . ?
C20 C21 C22 C26 -179.4(3) . . . . ?
C21 C16 C17 C7 179.5(3) . . . . ?
C21 C16 C17 C18 1.5(4) . . . . ?
C21 C20 C25 C24 -0.3(6) . . . . ?
C21 C22 C23 C24 -0.3(6) . . . . ?
C21 C22 C26 C27 -98.1(4) . . . . ?
C21 C22 C26 C31 88.2(5) . . . . ?
C22 C23 C24 C25 -1.0(6) . . . . ?
C22 C26 C27 C28 -177.5(4) . . . . ?
C22 C26 C31 C30 176.9(4) . . . . ?
C23 C22 C26 C27 81.2(4) . . . . ?
C23 C22 C26 C31 -92.5(5) . . . . ?
C23 C24 C25 C20 1.3(6) . . . . ?
C25 C20 C21 C16 178.1(3) . . . . ?
C25 C20 C21 C22 -1.0(5) . . . . ?
C26 C22 C23 C24 -179.7(4) . . . . ?
C26 C27 C28 C29 2.8(8) . . . . ?
C27 C26 C31 C30 3.0(7) . . . . ?
C27 C28 C29 C30 -1.4(8) . . . . ?
C28 C29 C30 C31 1.0(9) . . . . ?
C29 C30 C31 C26 -1.8(9) . . . . ?
C31 C26 C27 C28 -3.5(7) . . . . ?
O1 C5 C6 C1 179.4(2) . . . . ?
O1 C5 C6 C7 -1.9(3) . . . . ?
O2 C8 O1 C5 -178.6(3) . . . . ?
O3 C16 C17 C7 0.0(4) . . . . ?
O3 C16 C17 C18 -178.1(3) . . . . ?
O3 C16 C21 C20 -179.1(3) . . . . ?
O3 C16 C21 C22 0.0(5) . . . . ?
O4 C19 C20 C21 -178.2(4) . . . . ?
O4 C19 C20 C25 1.3(7) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.828
_oxdiff_exptl_absorpt_empirical_full_min 0.496
