# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_0692_cole
_database_code_depnum_ccdc_archive 'CCDC 1965037'
loop_
_audit_author_name
_audit_author_address
'Alexander Filatov'
;the University of Chicago
United States of America
;
_audit_update_record             
;
2019-11-11 deposited with the CCDC.	2020-01-22 downloaded from the CCDC.
;
_audit_creation_date             2018-10-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 O6'
_chemical_formula_sum            'C21 H20 O6'
_chemical_formula_weight         368.37
_chemical_absolute_configuration .
_chemical_melting_point          ?
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'

_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      orthorhombic
_space_group_IT_number           19
_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                   8.6977(4)
_cell_length_b                   9.9164(4)
_cell_length_c                   20.6241(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1778.83(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3731
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. 
wR2(int) was 0.0905 before and 0.0437 after correction. 
The Ratio of minimum to maximum transmission is 0.8512. 
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0908
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            6802
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.733
_diffrn_reflns_theta_min         2.279
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus X-ray tube'
_diffrn_source_type              'INCOATEC ImuS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                3440
_reflns_number_total             4513
_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       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material  
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'XL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'XT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 1142 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4513
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.040
_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)+(0.0368P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1140
_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 Ternary CH refined with riding coordinates:
 C8(H8), C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.2542(2) 0.22762(19) 0.66429(10) 0.0175(5) Uani 1 1 d . . . . .
O2 O 0.4050(3) 0.1586(2) 0.74418(11) 0.0220(5) Uani 1 1 d . . . . .
O3 O -0.0282(3) 0.5312(2) 0.61691(13) 0.0309(6) Uani 1 1 d . . . . .
O4 O 0.0739(2) 0.6603(2) 0.69520(11) 0.0216(5) Uani 1 1 d . . . . .
O5 O 0.7568(3) 0.8069(2) 0.44178(11) 0.0263(5) Uani 1 1 d . . . . .
O6 O 0.7612(3) 0.5838(2) 0.42418(11) 0.0252(5) Uani 1 1 d . . . . .
C1 C 0.6159(3) 0.2657(3) 0.61497(14) 0.0152(6) Uani 1 1 d . . . . .
C2 C 0.7516(4) 0.2333(3) 0.64668(15) 0.0189(6) Uani 1 1 d . . . . .
H2 H 0.790510 0.289921 0.679996 0.023 Uiso 1 1 calc R . . . .
C3 C 0.8299(4) 0.1163(3) 0.62898(16) 0.0223(7) Uani 1 1 d . . . . .
H3 H 0.923493 0.093250 0.649984 0.027 Uiso 1 1 calc R . . . .
C4 C 0.7712(4) 0.0334(3) 0.58059(15) 0.0222(7) Uani 1 1 d . . . . .
H4 H 0.824901 -0.046443 0.568956 0.027 Uiso 1 1 calc R . . . .
C5 C 0.6358(4) 0.0656(3) 0.54923(16) 0.0197(7) Uani 1 1 d . . . . .
H5 H 0.596247 0.008630 0.516170 0.024 Uiso 1 1 calc R . . . .
C6 C 0.5583(3) 0.1828(3) 0.56680(14) 0.0157(6) Uani 1 1 d . . . . .
C7 C 0.4097(4) 0.2370(3) 0.53959(16) 0.0188(7) Uani 1 1 d . . . . .
H7A H 0.331(4) 0.171(3) 0.5408(15) 0.012(8) Uiso 1 1 d . . . . .
H7B H 0.421(4) 0.264(4) 0.4960(17) 0.019(9) Uiso 1 1 d . . . . .
C8 C 0.3729(3) 0.3629(3) 0.58070(15) 0.0159(6) Uani 1 1 d . . . . .
H8 H 0.360348 0.443061 0.551743 0.019 Uiso 1 1 calc R . . . .
C9 C 0.5125(3) 0.3858(3) 0.62756(15) 0.0142(6) Uani 1 1 d . . . . .
C10 C 0.2283(4) 0.3445(3) 0.62193(15) 0.0158(6) Uani 1 1 d . . . . .
H10 H 0.136010 0.330192 0.593847 0.019 Uiso 1 1 calc R . . . .
C11 C 0.3715(4) 0.2458(3) 0.70633(14) 0.0166(6) Uani 1 1 d . . . . .
C12 C 0.4481(3) 0.3814(3) 0.69886(14) 0.0147(6) Uani 1 1 d . . . . .
H12 H 0.531487 0.394788 0.731617 0.018 Uiso 1 1 calc R . . . .
C13 C 0.3232(3) 0.4863(3) 0.70541(15) 0.0155(6) Uani 1 1 d . . . . .
H13 H 0.327156 0.558702 0.735515 0.019 Uiso 1 1 calc R . . . .
C14 C 0.2072(3) 0.4666(3) 0.66469(15) 0.0152(6) Uani 1 1 d . . . . .
C15 C 0.0716(4) 0.5539(3) 0.65559(16) 0.0191(7) Uani 1 1 d . . . . .
C16 C -0.0488(4) 0.7561(4) 0.6849(2) 0.0313(8) Uani 1 1 d . . . . .
H16A H -0.037993 0.831130 0.715486 0.047 Uiso 1 1 calc GR . . . .
H16B H -0.148095 0.711631 0.691743 0.047 Uiso 1 1 calc GR . . . .
H16C H -0.043583 0.790643 0.640409 0.047 Uiso 1 1 calc GR . . . .
C17 C 0.5944(3) 0.5216(3) 0.61771(14) 0.0153(6) Uani 1 1 d . . . . .
H17A H 0.521580 0.595124 0.628334 0.018 Uiso 1 1 calc R . . . .
H17B H 0.681140 0.527472 0.648670 0.018 Uiso 1 1 calc R . . . .
C18 C 0.6547(3) 0.5442(3) 0.55091(15) 0.0163(6) Uani 1 1 d . . . . .
H18 H 0.697772 0.469589 0.528445 0.020 Uiso 1 1 calc R . . . .
C19 C 0.6515(4) 0.6624(3) 0.52123(15) 0.0190(7) Uani 1 1 d . . . . .
H19 H 0.595513 0.732931 0.541540 0.023 Uiso 1 1 calc R . . . .
C20 C 0.7274(4) 0.6933(3) 0.45951(15) 0.0182(6) Uani 1 1 d . . . . .
C21 C 0.8400(4) 0.6083(3) 0.36405(16) 0.0250(8) Uani 1 1 d . . . . .
H21A H 0.944344 0.640665 0.373047 0.038 Uiso 1 1 calc GR . . . .
H21B H 0.784069 0.676549 0.339066 0.038 Uiso 1 1 calc GR . . . .
H21C H 0.845436 0.524407 0.339039 0.038 Uiso 1 1 calc GR . . . .


_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 C10 1.469(3) . ?
O1 C11 1.352(4) . ?
O2 C11 1.201(4) . ?
O3 C15 1.201(4) . ?
O4 C15 1.335(4) . ?
O4 C16 1.445(4) . ?
O5 C20 1.211(4) . ?
O6 C20 1.341(4) . ?
O6 C21 1.438(4) . ?
C1 C2 1.387(4) . ?
C1 C6 1.384(4) . ?
C1 C9 1.515(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(4) . ?
C6 C7 1.508(4) . ?
C7 H7A 0.94(3) . ?
C7 H7B 0.94(3) . ?
C7 C8 1.543(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.568(4) . ?
C8 C10 1.529(4) . ?
C9 C12 1.574(4) . ?
C9 C17 1.537(4) . ?
C10 H10 1.0000 . ?
C10 C14 1.509(4) . ?
C11 C12 1.509(4) . ?
C12 H12 1.0000 . ?
C12 C13 1.511(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.327(4) . ?
C14 C15 1.475(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.491(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.322(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.467(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C11 O1 C10 113.1(2) . . ?
C15 O4 C16 114.8(3) . . ?
C20 O6 C21 115.9(2) . . ?
C2 C1 C9 127.4(3) . . ?
C6 C1 C2 120.6(3) . . ?
C6 C1 C9 112.0(3) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C5 120.5(3) . . ?
C1 C6 C7 111.4(3) . . ?
C5 C6 C7 128.1(3) . . ?
C6 C7 H7A 111.2(19) . . ?
C6 C7 H7B 112(2) . . ?
C6 C7 C8 105.2(3) . . ?
H7A C7 H7B 107(3) . . ?
C8 C7 H7A 113.2(19) . . ?
C8 C7 H7B 109(2) . . ?
C7 C8 H8 109.7 . . ?
C7 C8 C9 107.2(2) . . ?
C9 C8 H8 109.7 . . ?
C10 C8 C7 112.3(2) . . ?
C10 C8 H8 109.7 . . ?
C10 C8 C9 108.1(2) . . ?
C1 C9 C8 103.9(2) . . ?
C1 C9 C12 110.5(2) . . ?
C1 C9 C17 113.0(2) . . ?
C8 C9 C12 107.2(2) . . ?
C17 C9 C8 113.8(2) . . ?
C17 C9 C12 108.2(2) . . ?
O1 C10 C8 107.4(2) . . ?
O1 C10 H10 110.8 . . ?
O1 C10 C14 107.7(2) . . ?
C8 C10 H10 110.8 . . ?
C14 C10 C8 109.2(2) . . ?
C14 C10 H10 110.8 . . ?
O1 C11 C12 112.7(2) . . ?
O2 C11 O1 120.3(3) . . ?
O2 C11 C12 127.0(3) . . ?
C9 C12 H12 111.7 . . ?
C11 C12 C9 106.1(2) . . ?
C11 C12 H12 111.7 . . ?
C11 C12 C13 106.7(2) . . ?
C13 C12 C9 108.7(2) . . ?
C13 C12 H12 111.7 . . ?
C12 C13 H13 123.6 . . ?
C14 C13 C12 112.9(3) . . ?
C14 C13 H13 123.6 . . ?
C13 C14 C10 113.3(3) . . ?
C13 C14 C15 127.0(3) . . ?
C15 C14 C10 119.6(3) . . ?
O3 C15 O4 124.4(3) . . ?
O3 C15 C14 123.6(3) . . ?
O4 C15 C14 112.0(3) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 C17 H17A 108.6 . . ?
C9 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C18 C17 C9 114.6(2) . . ?
C18 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C17 C18 H18 118.2 . . ?
C19 C18 C17 123.6(3) . . ?
C19 C18 H18 118.2 . . ?
C18 C19 H19 117.3 . . ?
C18 C19 C20 125.3(3) . . ?
C20 C19 H19 117.3 . . ?
O5 C20 O6 122.9(3) . . ?
O5 C20 C19 123.5(3) . . ?
O6 C20 C19 113.6(3) . . ?
O6 C21 H21A 109.5 . . ?
O6 C21 H21B 109.5 . . ?
O6 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_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_mo_0680_am_cc04_073_5_0m
_database_code_depnum_ccdc_archive 'CCDC 1965040'
loop_
_audit_author_name
_audit_author_address
'Alexander Filatov'
;the University of Chicago
United States of America
;
_audit_update_record             
;
2019-11-11 deposited with the CCDC.	2020-01-22 downloaded from the CCDC.
;
_audit_creation_date             2018-10-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H21 Br O5, C15 H11 Br O4'
_chemical_formula_sum            'C37 H32 Br2 O9'
_chemical_formula_weight         780.44
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.4799(6)
_cell_length_b                   12.7561(5)
_cell_length_c                   17.7032(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.4710(10)
_cell_angle_gamma                90
_cell_volume                     3275.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9830
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.606
_shelx_estimated_absorpt_T_min   0.480
_exptl_absorpt_coefficient_mu    2.533
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1068 before and 0.0459 after correction. 
The Ratio of minimum to maximum transmission is 0.7143. 
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            54277
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.719
_diffrn_reflns_theta_min         2.126
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus X-ray tube'
_diffrn_source_type              'INCOATEC ImuS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6109
_reflns_number_total             7686
_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       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material  
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'XL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'XT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         7686
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0327P)²+2.7001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0726
_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 Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C14(H14), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
 C25(H25), C26(H26), C28(H28), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Br1 Br 0.07686(2) 0.39931(2) 0.42942(2) 0.02535(7) Uani 1 1 d . . . . .
O1 O 0.08885(12) 0.95173(13) 0.48175(9) 0.0365(4) Uani 1 1 d . . . . .
O2 O 0.14846(12) 0.81686(13) 0.56358(10) 0.0351(4) Uani 1 1 d . . . . .
O3 O 0.12204(10) 0.35446(11) 0.27752(9) 0.0244(3) Uani 1 1 d . . . . .
O4 O 0.13141(10) 0.51686(11) 0.23605(8) 0.0200(3) Uani 1 1 d . . . . .
O5 O 0.22287(10) 0.81564(12) 0.32172(9) 0.0266(3) Uani 1 1 d . . . . .
C1 C 0.15019(19) 1.02020(19) 0.54016(14) 0.0355(6) Uani 1 1 d . . . . .
H1A H 0.138720 1.092773 0.521097 0.053 Uiso 1 1 calc GR . . . .
H1B H 0.214087 1.001286 0.547932 0.053 Uiso 1 1 calc GR . . . .
H1C H 0.139768 1.013454 0.591449 0.053 Uiso 1 1 calc GR . . . .
C2 C 0.09560(16) 0.85132(19) 0.50106(14) 0.0281(5) Uani 1 1 d . . . . .
C3 C 0.02889(16) 0.78986(19) 0.43448(14) 0.0310(5) Uani 1 1 d . . . . .
H3 H -0.014856 0.825684 0.390624 0.037 Uiso 1 1 calc R . . . .
C4 C 0.02963(15) 0.68704(19) 0.43546(14) 0.0280(5) Uani 1 1 d . . . . .
H4 H 0.074699 0.653178 0.479598 0.034 Uiso 1 1 calc R . . . .
C5 C -0.03571(15) 0.61944(19) 0.37178(14) 0.0265(5) Uani 1 1 d . . . . .
H5A H -0.089009 0.663321 0.340594 0.032 Uiso 1 1 calc R . . . .
H5B H -0.059243 0.564581 0.399125 0.032 Uiso 1 1 calc R . . . .
C6 C 0.00111(14) 0.56437(16) 0.31104(12) 0.0194(4) Uani 1 1 d . . . . .
C7 C -0.07711(14) 0.49463(17) 0.25525(13) 0.0220(5) Uani 1 1 d . . . . .
H7A H -0.051636 0.432679 0.236597 0.026 Uiso 1 1 calc R . . . .
H7B H -0.118628 0.470557 0.283417 0.026 Uiso 1 1 calc R . . . .
C8 C -0.12789(15) 0.56612(19) 0.18492(14) 0.0295(5) Uani 1 1 d . . . . .
H8A H -0.165304 0.525011 0.137273 0.035 Uiso 1 1 calc R . . . .
H8B H -0.168569 0.615676 0.199711 0.035 Uiso 1 1 calc R . . . .
C9 C -0.05012(15) 0.62368(18) 0.16867(13) 0.0261(5) Uani 1 1 d . . . . .
H9A H -0.072343 0.690705 0.140350 0.031 Uiso 1 1 calc R . . . .
H9B H -0.024189 0.580263 0.135405 0.031 Uiso 1 1 calc R . . . .
C10 C 0.02269(14) 0.64348(16) 0.25282(12) 0.0199(4) Uani 1 1 d . . . . .
H10 H 0.015707 0.716617 0.270206 0.024 Uiso 1 1 calc R . . . .
C11 C 0.12219(14) 0.62699(16) 0.25687(12) 0.0190(4) Uani 1 1 d . . . . .
H11 H 0.137939 0.675665 0.219329 0.023 Uiso 1 1 calc R . . . .
C12 C 0.11666(13) 0.44675(17) 0.28711(12) 0.0187(4) Uani 1 1 d . . . . .
C13 C 0.09186(14) 0.50166(16) 0.35377(12) 0.0182(4) Uani 1 1 d . . . . .
C14 C 0.16959(13) 0.57643(16) 0.39366(12) 0.0178(4) Uani 1 1 d . . . . .
H14 H 0.204058 0.575685 0.449828 0.021 Uiso 1 1 calc R . . . .
C15 C 0.18529(13) 0.64371(16) 0.34251(12) 0.0180(4) Uani 1 1 d . . . . .
C16 C 0.24244(13) 0.73949(17) 0.36625(12) 0.0195(4) Uani 1 1 d . . . . .
C17 C 0.31749(14) 0.74249(17) 0.44631(12) 0.0205(4) Uani 1 1 d . . . . .
C18 C 0.33557(16) 0.83689(19) 0.48836(14) 0.0281(5) Uani 1 1 d . . . . .
H18 H 0.300168 0.897435 0.465907 0.034 Uiso 1 1 calc R . . . .
C19 C 0.40543(18) 0.8424(2) 0.56314(15) 0.0383(6) Uani 1 1 d . . . . .
H19 H 0.416598 0.906119 0.592772 0.046 Uiso 1 1 calc R . . . .
C20 C 0.45840(17) 0.7555(2) 0.59427(14) 0.0395(7) Uani 1 1 d . . . . .
H20 H 0.506667 0.760067 0.645165 0.047 Uiso 1 1 calc R . . . .
C21 C 0.44251(16) 0.6617(2) 0.55265(14) 0.0327(6) Uani 1 1 d . . . . .
H21 H 0.480236 0.602528 0.574383 0.039 Uiso 1 1 calc R . . . .
C22 C 0.37090(14) 0.65457(18) 0.47870(13) 0.0232(5) Uani 1 1 d . . . . .
H22 H 0.358483 0.589843 0.450384 0.028 Uiso 1 1 calc R . . . .
Br2 Br 0.24766(2) 0.98814(2) 0.11650(2) 0.02368(7) Uani 1 1 d . . . . .
O6 O 0.36540(12) 0.44059(13) 0.32788(9) 0.0345(4) Uani 1 1 d . . . . .
O7 O 0.30639(10) 0.41334(11) 0.19427(9) 0.0244(3) Uani 1 1 d . . . . .
O8 O 0.46794(10) 0.93235(11) 0.32142(8) 0.0231(3) Uani 1 1 d . . . . .
O9 O 0.41026(12) 1.07934(12) 0.25815(10) 0.0350(4) Uani 1 1 d . . . . .
C23 C 0.29713(17) 0.30329(17) 0.20877(15) 0.0308(5) Uani 1 1 d . . . . .
H23A H 0.269785 0.266812 0.157149 0.046 Uiso 1 1 calc GR . . . .
H23B H 0.257261 0.294733 0.240851 0.046 Uiso 1 1 calc GR . . . .
H23C H 0.358054 0.273604 0.238173 0.046 Uiso 1 1 calc GR . . . .
C24 C 0.34121(14) 0.47346(17) 0.25973(13) 0.0220(5) Uani 1 1 d . . . . .
C25 C 0.34523(15) 0.58418(16) 0.23746(13) 0.0216(4) Uani 1 1 d . . . . .
H25 H 0.311427 0.607129 0.184229 0.026 Uiso 1 1 calc R . . . .
C26 C 0.39629(14) 0.65200(16) 0.29201(12) 0.0185(4) Uani 1 1 d . . . . .
H26 H 0.430486 0.625088 0.343928 0.022 Uiso 1 1 calc R . . . .
C27 C 0.40441(14) 0.76434(16) 0.27912(12) 0.0183(4) Uani 1 1 d . . . . .
C28 C 0.33758(14) 0.81476(16) 0.21090(12) 0.0193(4) Uani 1 1 d . . . . .
H28 H 0.293141 0.773574 0.171358 0.023 Uiso 1 1 calc R . . . .
C29 C 0.33728(14) 0.91868(16) 0.20252(12) 0.0196(4) Uani 1 1 d . . . . .
C30 C 0.40392(15) 0.98558(17) 0.25901(13) 0.0224(5) Uani 1 1 d . . . . .
C31 C 0.46871(14) 0.82614(16) 0.33320(12) 0.0186(4) Uani 1 1 d . . . . .
C32 C 0.54321(14) 0.79820(16) 0.40893(12) 0.0192(4) Uani 1 1 d . . . . .
C33 C 0.56698(15) 0.86951(17) 0.47269(13) 0.0233(5) Uani 1 1 d . . . . .
H33 H 0.534824 0.934198 0.466530 0.028 Uiso 1 1 calc R . . . .
C34 C 0.63681(15) 0.84714(19) 0.54477(13) 0.0268(5) Uani 1 1 d . . . . .
H34 H 0.652775 0.896636 0.587557 0.032 Uiso 1 1 calc R . . . .
C35 C 0.68342(15) 0.75267(19) 0.55456(13) 0.0282(5) Uani 1 1 d . . . . .
H35 H 0.730832 0.736703 0.604254 0.034 Uiso 1 1 calc R . . . .
C36 C 0.66066(15) 0.68186(19) 0.49180(13) 0.0280(5) Uani 1 1 d . . . . .
H36 H 0.692667 0.617010 0.498642 0.034 Uiso 1 1 calc R . . . .
C37 C 0.59169(14) 0.70397(17) 0.41878(13) 0.0230(5) Uani 1 1 d . . . . .
H37 H 0.577523 0.655117 0.375641 0.028 Uiso 1 1 calc R . . . .


_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
Br1 C13 1.942(2) . ?
O1 C1 1.431(3) . ?
O1 C2 1.320(3) . ?
O2 C2 1.206(3) . ?
O3 C12 1.197(3) . ?
O4 C11 1.472(2) . ?
O4 C12 1.347(2) . ?
O5 C16 1.221(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.490(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.312(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.497(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.550(3) . ?
C6 C7 1.548(3) . ?
C6 C10 1.560(3) . ?
C6 C13 1.563(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.522(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.521(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.542(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.531(3) . ?
C11 H11 1.0000 . ?
C11 C15 1.504(3) . ?
C12 C13 1.532(3) . ?
C13 C14 1.504(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.330(3) . ?
C15 C16 1.480(3) . ?
C16 C17 1.486(3) . ?
C17 C18 1.392(3) . ?
C17 C22 1.392(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.388(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.374(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.381(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.391(3) . ?
C22 H22 0.9500 . ?
Br2 C29 1.884(2) . ?
O6 C24 1.206(3) . ?
O7 C23 1.443(3) . ?
O7 C24 1.336(3) . ?
O8 C30 1.378(2) . ?
O8 C31 1.370(2) . ?
O9 C30 1.201(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.474(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.331(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.463(3) . ?
C27 C28 1.438(3) . ?
C27 C31 1.365(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.334(3) . ?
C29 C30 1.439(3) . ?
C31 C32 1.474(3) . ?
C32 C33 1.395(3) . ?
C32 C37 1.395(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.383(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.384(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.379(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.387(3) . ?
C37 H37 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
C2 O1 C1 115.64(18) . . ?
C12 O4 C11 114.31(15) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 109.6(2) . . ?
O2 C2 O1 123.9(2) . . ?
O2 C2 C3 126.5(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 117.8 . . ?
C3 C4 C5 124.4(2) . . ?
C5 C4 H4 117.8 . . ?
C4 C5 H5A 107.8 . . ?
C4 C5 H5B 107.8 . . ?
C4 C5 C6 117.90(18) . . ?
H5A C5 H5B 107.2 . . ?
C6 C5 H5A 107.8 . . ?
C6 C5 H5B 107.8 . . ?
C5 C6 C10 112.38(17) . . ?
C5 C6 C13 112.49(17) . . ?
C7 C6 C5 107.92(16) . . ?
C7 C6 C10 104.52(16) . . ?
C7 C6 C13 112.63(17) . . ?
C10 C6 C13 106.68(16) . . ?
C6 C7 H7A 110.9 . . ?
C6 C7 H7B 110.9 . . ?
H7A C7 H7B 109.0 . . ?
C8 C7 C6 104.04(17) . . ?
C8 C7 H7A 110.9 . . ?
C8 C7 H7B 110.9 . . ?
C7 C8 H8A 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
C9 C8 C7 103.15(17) . . ?
C9 C8 H8A 111.1 . . ?
C9 C8 H8B 111.1 . . ?
C8 C9 H9A 110.8 . . ?
C8 C9 H9B 110.8 . . ?
C8 C9 C10 104.82(18) . . ?
H9A C9 H9B 108.9 . . ?
C10 C9 H9A 110.8 . . ?
C10 C9 H9B 110.8 . . ?
C6 C10 H10 109.2 . . ?
C9 C10 C6 106.21(16) . . ?
C9 C10 H10 109.2 . . ?
C11 C10 C6 108.94(16) . . ?
C11 C10 C9 113.96(18) . . ?
C11 C10 H10 109.2 . . ?
O4 C11 C10 107.66(16) . . ?
O4 C11 H11 111.0 . . ?
O4 C11 C15 107.58(16) . . ?
C10 C11 H11 111.0 . . ?
C15 C11 C10 108.41(16) . . ?
C15 C11 H11 111.0 . . ?
O3 C12 O4 121.45(19) . . ?
O3 C12 C13 127.42(19) . . ?
O4 C12 C13 111.12(17) . . ?
C6 C13 Br1 111.95(13) . . ?
C12 C13 Br1 110.28(14) . . ?
C12 C13 C6 106.63(16) . . ?
C14 C13 Br1 111.82(14) . . ?
C14 C13 C6 109.80(16) . . ?
C14 C13 C12 106.07(16) . . ?
C13 C14 H14 123.3 . . ?
C15 C14 C13 113.34(18) . . ?
C15 C14 H14 123.3 . . ?
C14 C15 C11 112.69(18) . . ?
C14 C15 C16 124.93(19) . . ?
C16 C15 C11 121.07(18) . . ?
O5 C16 C15 119.00(18) . . ?
O5 C16 C17 122.02(19) . . ?
C15 C16 C17 118.83(18) . . ?
C18 C17 C16 118.4(2) . . ?
C18 C17 C22 119.8(2) . . ?
C22 C17 C16 121.71(19) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.9(2) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 119.9(2) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.0(2) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.6(2) . . ?
C22 C21 H21 120.2 . . ?
C17 C22 H22 120.1 . . ?
C21 C22 C17 119.8(2) . . ?
C21 C22 H22 120.1 . . ?
C24 O7 C23 116.04(17) . . ?
C31 O8 C30 125.10(16) . . ?
O7 C23 H23A 109.5 . . ?
O7 C23 H23B 109.5 . . ?
O7 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O6 C24 O7 123.9(2) . . ?
O6 C24 C25 125.0(2) . . ?
O7 C24 C25 111.10(18) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 119.91(19) . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 117.1 . . ?
C25 C26 C27 125.79(19) . . ?
C27 C26 H26 117.1 . . ?
C28 C27 C26 119.54(18) . . ?
C31 C27 C26 122.52(18) . . ?
C31 C27 C28 117.69(19) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.76(19) . . ?
C29 C28 H28 119.6 . . ?
C28 C29 Br2 122.02(16) . . ?
C28 C29 C30 122.57(19) . . ?
C30 C29 Br2 115.40(15) . . ?
O8 C30 C29 113.88(18) . . ?
O9 C30 O8 117.53(19) . . ?
O9 C30 C29 128.6(2) . . ?
O8 C31 C32 109.87(17) . . ?
C27 C31 O8 119.94(18) . . ?
C27 C31 C32 130.17(19) . . ?
C33 C32 C31 118.64(19) . . ?
C33 C32 C37 118.84(19) . . ?
C37 C32 C31 122.51(19) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 C32 120.8(2) . . ?
C34 C33 H33 119.6 . . ?
C33 C34 H34 120.0 . . ?
C33 C34 C35 120.0(2) . . ?
C35 C34 H34 120.0 . . ?
C34 C35 H35 120.2 . . ?
C36 C35 C34 119.6(2) . . ?
C36 C35 H35 120.2 . . ?
C35 C36 H36 119.5 . . ?
C35 C36 C37 120.9(2) . . ?
C37 C36 H36 119.5 . . ?
C32 C37 H37 120.1 . . ?
C36 C37 C32 119.8(2) . . ?
C36 C37 H37 120.1 . . ?

_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_0685_cole
_database_code_depnum_ccdc_archive 'CCDC 1965043'
loop_
_audit_author_name
_audit_author_address
'Alexander Filatov'
;the University of Chicago
United States of America
;
_audit_update_record             
;
2019-11-11 deposited with the CCDC.	2020-01-22 downloaded from the CCDC.
;
_audit_creation_date             2018-10-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 O6'
_chemical_formula_sum            'C20 H20 O6'
_chemical_formula_weight         356.36
_chemical_melting_point          ?
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.1979(9)
_cell_length_b                   12.5205(10)
_cell_length_c                   24.904(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.401(2)
_cell_angle_gamma                90
_cell_volume                     3485.5(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8674
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.28
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1522 before and 0.0741 after correction. 
The Ratio of minimum to maximum transmission is 0.7984. 
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            41322
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.460
_diffrn_reflns_theta_min         2.309
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  D8Venture
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus X-ray tube'
_diffrn_source_type              'INCOATEC ImuS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4102
_reflns_number_total             6449
_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       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material  
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.850
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         6449
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1373
_refine_ls_R_factor_gt           0.0846
_refine_ls_restrained_S_all      1.066
_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)+(0.0965P)²+7.9739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1990
_refine_ls_wR_factor_ref         0.2260
_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 Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C25(H25), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C16(H16A,H16B), C28(H28A,H28B), C36(H36A,H36B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18),
 C24(H24), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C37(H37), C38(H38)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C40(H40A,H40B,H40C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.7906(2) 0.1870(2) 0.83049(11) 0.0222(7) Uani 1 1 d . . . . .
O2 O 0.9647(2) 0.2234(2) 0.87687(11) 0.0224(7) Uani 1 1 d . . . . .
O3 O 1.0691(2) 0.4097(2) 0.76110(11) 0.0220(7) Uani 1 1 d . . . . .
O4 O 0.9894(3) 0.5210(2) 0.70017(12) 0.0268(7) Uani 1 1 d . . . . .
O5 O 1.1417(3) -0.0575(3) 0.52091(12) 0.0340(8) Uani 1 1 d . . . . .
O6 O 1.2305(2) -0.0777(2) 0.60281(11) 0.0241(7) Uani 1 1 d . . . . .
C1 C 0.7442(4) 0.1468(4) 0.87922(17) 0.0287(11) Uani 1 1 d . . . . .
H1A H 0.660271 0.126126 0.872244 0.043 Uiso 1 1 calc GR . . . .
H1B H 0.749776 0.202481 0.906908 0.043 Uiso 1 1 calc GR . . . .
H1C H 0.790841 0.084412 0.891690 0.043 Uiso 1 1 calc GR . . . .
C2 C 0.9026(3) 0.2230(3) 0.83576(16) 0.0170(9) Uani 1 1 d . . . . .
C3 C 0.9395(3) 0.2661(3) 0.78362(16) 0.0157(9) Uani 1 1 d . . . . .
C4 C 0.8683(3) 0.2861(3) 0.74077(16) 0.0156(9) Uani 1 1 d . . . . .
H4 H 0.784986 0.271143 0.739061 0.019 Uiso 1 1 calc R . . . .
C5 C 0.9298(3) 0.3339(3) 0.69540(16) 0.0168(9) Uani 1 1 d . . . . .
H5 H 0.872047 0.352639 0.664674 0.020 Uiso 1 1 calc R . . . .
C6 C 0.9963(3) 0.4314(3) 0.71726(16) 0.0167(9) Uani 1 1 d . . . . .
C7 C 1.0677(3) 0.2963(3) 0.77600(16) 0.0160(9) Uani 1 1 d . . . . .
H7 H 1.119357 0.282748 0.809451 0.019 Uiso 1 1 calc R . . . .
C8 C 1.1135(3) 0.2354(3) 0.72807(16) 0.0196(9) Uani 1 1 d . . . . .
H8A H 1.117801 0.158170 0.736517 0.023 Uiso 1 1 calc R . . . .
H8B H 1.195113 0.260261 0.721113 0.023 Uiso 1 1 calc R . . . .
C9 C 1.0296(3) 0.2534(3) 0.67756(16) 0.0170(9) Uani 1 1 d . . . . .
C10 C 1.0871(3) 0.3002(3) 0.62812(16) 0.0162(9) Uani 1 1 d . . . . .
C11 C 1.0117(4) 0.3279(4) 0.58337(17) 0.0277(11) Uani 1 1 d . . . . .
H11 H 0.927668 0.320265 0.585386 0.033 Uiso 1 1 calc R . . . .
C12 C 1.0559(4) 0.3662(4) 0.53644(18) 0.0314(11) Uani 1 1 d . . . . .
H12 H 1.003030 0.384229 0.506564 0.038 Uiso 1 1 calc R . . . .
C13 C 1.1778(4) 0.3777(4) 0.53362(19) 0.0312(11) Uani 1 1 d . . . . .
H13 H 1.209255 0.403337 0.501453 0.037 Uiso 1 1 calc R . . . .
C14 C 1.2537(4) 0.3525(3) 0.57678(18) 0.0263(10) Uani 1 1 d . . . . .
H14 H 1.337354 0.362992 0.574993 0.032 Uiso 1 1 calc R . . . .
C15 C 1.2082(4) 0.3114(3) 0.62339(17) 0.0201(9) Uani 1 1 d . . . . .
H15 H 1.261926 0.290779 0.652495 0.024 Uiso 1 1 calc R . . . .
C16 C 0.9679(3) 0.1455(3) 0.66053(17) 0.0189(9) Uani 1 1 d . . . . .
H16A H 0.930106 0.114242 0.691852 0.023 Uiso 1 1 calc R . . . .
H16B H 0.904202 0.159350 0.632123 0.023 Uiso 1 1 calc R . . . .
C17 C 1.0553(3) 0.0678(3) 0.64013(17) 0.0192(9) Uani 1 1 d . . . . .
H17 H 1.112753 0.038483 0.665590 0.023 Uiso 1 1 calc R . . . .
C18 C 1.0596(4) 0.0361(3) 0.58967(17) 0.0239(10) Uani 1 1 d . . . . .
H18 H 1.002074 0.062050 0.563269 0.029 Uiso 1 1 calc R . . . .
C19 C 1.1524(4) -0.0389(3) 0.57390(16) 0.0198(9) Uani 1 1 d . . . . .
C20 C 1.2310(5) -0.1268(4) 0.49930(19) 0.0431(14) Uani 1 1 d . . . . .
H20A H 1.222090 -0.125889 0.459920 0.065 Uiso 1 1 calc GR . . . .
H20B H 1.220060 -0.199811 0.512282 0.065 Uiso 1 1 calc GR . . . .
H20C H 1.311044 -0.101384 0.511114 0.065 Uiso 1 1 calc GR . . . .
O7 O 0.5339(2) 0.5233(2) 0.61930(10) 0.0179(6) Uani 1 1 d . . . . .
O8 O 0.7083(2) 0.5502(2) 0.66726(11) 0.0185(6) Uani 1 1 d . . . . .
O9 O 0.4192(2) 0.3297(2) 0.73145(11) 0.0211(7) Uani 1 1 d . . . . .
O10 O 0.4916(3) 0.2157(2) 0.79256(12) 0.0267(7) Uani 1 1 d . . . . .
O11 O 0.2954(2) 0.8243(2) 0.90377(11) 0.0218(7) Uani 1 1 d . . . . .
O12 O 0.4377(3) 0.8322(2) 0.97178(11) 0.0262(7) Uani 1 1 d . . . . .
C21 C 0.7579(4) 0.5958(4) 0.62002(17) 0.0253(10) Uani 1 1 d . . . . .
H21A H 0.759416 0.541409 0.591762 0.038 Uiso 1 1 calc GR . . . .
H21B H 0.839547 0.620700 0.629207 0.038 Uiso 1 1 calc GR . . . .
H21C H 0.708382 0.656116 0.607102 0.038 Uiso 1 1 calc GR . . . .
C22 C 0.5954(3) 0.5174(3) 0.66062(15) 0.0136(8) Uani 1 1 d . . . . .
C23 C 0.5555(3) 0.4703(3) 0.71076(15) 0.0124(8) Uani 1 1 d . . . . .
C24 C 0.6235(3) 0.4478(3) 0.75474(15) 0.0147(8) Uani 1 1 d . . . . .
H24 H 0.707172 0.461138 0.757639 0.018 Uiso 1 1 calc R . . . .
C25 C 0.5580(3) 0.3999(3) 0.79926(16) 0.0172(9) Uani 1 1 d . . . . .
H25 H 0.613098 0.379489 0.830652 0.021 Uiso 1 1 calc R . . . .
C26 C 0.4891(3) 0.3052(3) 0.77604(15) 0.0169(9) Uani 1 1 d . . . . .
C27 C 0.4262(3) 0.4439(3) 0.71670(15) 0.0135(8) Uani 1 1 d . . . . .
H27 H 0.376884 0.459253 0.682780 0.016 Uiso 1 1 calc R . . . .
C28 C 0.3799(3) 0.5052(3) 0.76410(15) 0.0179(9) Uani 1 1 d . . . . .
H28A H 0.296960 0.482658 0.769935 0.021 Uiso 1 1 calc R . . . .
H28B H 0.378996 0.582617 0.755960 0.021 Uiso 1 1 calc R . . . .
C29 C 0.4598(3) 0.4844(3) 0.81536(15) 0.0158(9) Uani 1 1 d . . . . .
C30 C 0.3953(3) 0.4393(3) 0.86321(15) 0.0140(8) Uani 1 1 d . . . . .
C31 C 0.2738(4) 0.4376(3) 0.86634(17) 0.0208(9) Uani 1 1 d . . . . .
H31 H 0.224383 0.465296 0.837268 0.025 Uiso 1 1 calc R . . . .
C32 C 0.2204(4) 0.3963(4) 0.91113(18) 0.0274(11) Uani 1 1 d . . . . .
H32 H 0.135667 0.394272 0.911695 0.033 Uiso 1 1 calc R . . . .
C33 C 0.2890(4) 0.3590(4) 0.95399(18) 0.0293(11) Uani 1 1 d . . . . .
H33 H 0.252931 0.332075 0.984823 0.035 Uiso 1 1 calc R . . . .
C34 C 0.4110(4) 0.3608(5) 0.9519(2) 0.0450(15) Uani 1 1 d . . . . .
H34 H 0.459828 0.334222 0.981410 0.054 Uiso 1 1 calc R . . . .
C35 C 0.4635(4) 0.4006(4) 0.90755(18) 0.0373(13) Uani 1 1 d . . . . .
H35 H 0.548310 0.401734 0.907172 0.045 Uiso 1 1 calc R . . . .
C36 C 0.5285(3) 0.5871(3) 0.83383(16) 0.0165(9) Uani 1 1 d . . . . .
H36A H 0.592138 0.567912 0.861438 0.020 Uiso 1 1 calc R . . . .
H36B H 0.567415 0.618245 0.802765 0.020 Uiso 1 1 calc R . . . .
C37 C 0.4489(3) 0.6685(3) 0.85639(16) 0.0173(9) Uani 1 1 d . . . . .
H37 H 0.379102 0.689185 0.835418 0.021 Uiso 1 1 calc R . . . .
C38 C 0.4696(4) 0.7137(3) 0.90382(16) 0.0210(9) Uani 1 1 d . . . . .
H38 H 0.538845 0.693250 0.925257 0.025 Uiso 1 1 calc R . . . .
C39 C 0.3901(4) 0.7940(3) 0.92456(16) 0.0187(9) Uani 1 1 d . . . . .
C40 C 0.3717(4) 0.9147(4) 0.99706(18) 0.0286(11) Uani 1 1 d . . . . .
H40A H 0.376992 0.981181 0.976559 0.043 Uiso 1 1 calc GR . . . .
H40B H 0.405316 0.925933 1.033850 0.043 Uiso 1 1 calc GR . . . .
H40C H 0.287651 0.893260 0.997997 0.043 Uiso 1 1 calc GR . . . .


_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 1.439(5) . ?
O1 C2 1.332(5) . ?
O2 C2 1.203(5) . ?
O3 C6 1.351(5) . ?
O3 C7 1.467(5) . ?
O4 C6 1.201(5) . ?
O5 C19 1.338(5) . ?
O5 C20 1.451(5) . ?
O6 C19 1.202(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.487(6) . ?
C3 C4 1.317(5) . ?
C3 C7 1.508(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.484(6) . ?
C5 H5 1.0000 . ?
C5 C6 1.514(5) . ?
C5 C9 1.589(5) . ?
C7 H7 1.0000 . ?
C7 C8 1.531(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.541(5) . ?
C9 C10 1.539(5) . ?
C9 C16 1.564(5) . ?
C10 C11 1.402(6) . ?
C10 C15 1.375(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.367(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.393(6) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.490(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.321(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.471(6) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O7 C22 1.206(4) . ?
O8 C21 1.448(5) . ?
O8 C22 1.329(4) . ?
O9 C26 1.355(5) . ?
O9 C27 1.479(4) . ?
O10 C26 1.193(5) . ?
O11 C39 1.213(5) . ?
O12 C39 1.350(5) . ?
O12 C40 1.437(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.474(5) . ?
C23 C24 1.327(5) . ?
C23 C27 1.501(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.491(6) . ?
C25 H25 1.0000 . ?
C25 C26 1.511(5) . ?
C25 C29 1.594(5) . ?
C27 H27 1.0000 . ?
C27 C28 1.524(5) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.537(5) . ?
C29 C30 1.537(5) . ?
C29 C36 1.554(5) . ?
C30 C31 1.368(5) . ?
C30 C35 1.392(6) . ?
C31 H31 0.9500 . ?
C31 C32 1.396(6) . ?
C32 H32 0.9500 . ?
C32 C33 1.360(6) . ?
C33 H33 0.9500 . ?
C33 C34 1.371(7) . ?
C34 H34 0.9500 . ?
C34 C35 1.375(6) . ?
C35 H35 0.9500 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C36 C37 1.486(5) . ?
C37 H37 0.9500 . ?
C37 C38 1.318(6) . ?
C38 H38 0.9500 . ?
C38 C39 1.458(6) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 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
C2 O1 C1 114.9(3) . . ?
C6 O3 C7 112.6(3) . . ?
C19 O5 C20 116.5(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 110.2(3) . . ?
O2 C2 O1 125.4(4) . . ?
O2 C2 C3 124.4(4) . . ?
C2 C3 C7 121.1(3) . . ?
C4 C3 C2 126.2(4) . . ?
C4 C3 C7 112.7(4) . . ?
C3 C4 H4 123.0 . . ?
C3 C4 C5 114.1(3) . . ?
C5 C4 H4 123.0 . . ?
C4 C5 H5 111.6 . . ?
C4 C5 C6 107.0(3) . . ?
C4 C5 C9 108.8(3) . . ?
C6 C5 H5 111.6 . . ?
C6 C5 C9 105.9(3) . . ?
C9 C5 H5 111.6 . . ?
O3 C6 C5 112.9(3) . . ?
O4 C6 O3 119.8(4) . . ?
O4 C6 C5 127.3(4) . . ?
O3 C7 C3 107.4(3) . . ?
O3 C7 H7 111.1 . . ?
O3 C7 C8 106.0(3) . . ?
C3 C7 H7 111.1 . . ?
C3 C7 C8 109.8(3) . . ?
C8 C7 H7 111.1 . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C7 C8 C9 110.3(3) . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C8 C9 C5 105.6(3) . . ?
C8 C9 C16 109.5(3) . . ?
C10 C9 C5 108.5(3) . . ?
C10 C9 C8 116.4(3) . . ?
C10 C9 C16 108.1(3) . . ?
C16 C9 C5 108.5(3) . . ?
C11 C10 C9 118.0(4) . . ?
C15 C10 C9 124.7(4) . . ?
C15 C10 C11 117.2(4) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 C10 122.0(4) . . ?
C12 C11 H11 119.0 . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.0(4) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.5(4) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0(4) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C14 121.3(4) . . ?
C10 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C9 C16 H16A 109.3 . . ?
C9 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 C9 111.6(3) . . ?
C17 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C16 C17 H17 117.2 . . ?
C18 C17 C16 125.6(4) . . ?
C18 C17 H17 117.2 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.8(4) . . ?
C19 C18 H18 119.6 . . ?
O5 C19 C18 110.6(3) . . ?
O6 C19 O5 122.6(4) . . ?
O6 C19 C18 126.8(4) . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 O8 C21 115.4(3) . . ?
C26 O9 C27 112.7(3) . . ?
C39 O12 C40 116.7(3) . . ?
O8 C21 H21A 109.5 . . ?
O8 C21 H21B 109.5 . . ?
O8 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O7 C22 O8 125.3(4) . . ?
O7 C22 C23 124.1(3) . . ?
O8 C22 C23 110.6(3) . . ?
C22 C23 C27 121.0(3) . . ?
C24 C23 C22 126.6(4) . . ?
C24 C23 C27 112.4(3) . . ?
C23 C24 H24 122.7 . . ?
C23 C24 C25 114.5(3) . . ?
C25 C24 H24 122.7 . . ?
C24 C25 H25 112.1 . . ?
C24 C25 C26 107.1(3) . . ?
C24 C25 C29 107.3(3) . . ?
C26 C25 H25 112.1 . . ?
C26 C25 C29 105.8(3) . . ?
C29 C25 H25 112.1 . . ?
O9 C26 C25 113.2(3) . . ?
O10 C26 O9 119.7(4) . . ?
O10 C26 C25 127.2(4) . . ?
O9 C27 C23 107.6(3) . . ?
O9 C27 H27 111.2 . . ?
O9 C27 C28 105.6(3) . . ?
C23 C27 H27 111.2 . . ?
C23 C27 C28 109.8(3) . . ?
C28 C27 H27 111.2 . . ?
C27 C28 H28A 109.6 . . ?
C27 C28 H28B 109.6 . . ?
C27 C28 C29 110.5(3) . . ?
H28A C28 H28B 108.1 . . ?
C29 C28 H28A 109.6 . . ?
C29 C28 H28B 109.6 . . ?
C28 C29 C25 106.2(3) . . ?
C28 C29 C30 115.4(3) . . ?
C28 C29 C36 111.0(3) . . ?
C30 C29 C25 108.3(3) . . ?
C30 C29 C36 108.8(3) . . ?
C36 C29 C25 106.7(3) . . ?
C31 C30 C29 124.4(4) . . ?
C31 C30 C35 116.8(4) . . ?
C35 C30 C29 118.8(3) . . ?
C30 C31 H31 119.1 . . ?
C30 C31 C32 121.7(4) . . ?
C32 C31 H31 119.1 . . ?
C31 C32 H32 119.8 . . ?
C33 C32 C31 120.4(4) . . ?
C33 C32 H32 119.8 . . ?
C32 C33 H33 120.6 . . ?
C32 C33 C34 118.8(4) . . ?
C34 C33 H33 120.6 . . ?
C33 C34 H34 119.6 . . ?
C33 C34 C35 120.8(4) . . ?
C35 C34 H34 119.6 . . ?
C30 C35 H35 119.3 . . ?
C34 C35 C30 121.5(4) . . ?
C34 C35 H35 119.3 . . ?
C29 C36 H36A 109.1 . . ?
C29 C36 H36B 109.1 . . ?
H36A C36 H36B 107.8 . . ?
C37 C36 C29 112.5(3) . . ?
C37 C36 H36A 109.1 . . ?
C37 C36 H36B 109.1 . . ?
C36 C37 H37 118.1 . . ?
C38 C37 C36 123.8(4) . . ?
C38 C37 H37 118.1 . . ?
C37 C38 H38 118.8 . . ?
C37 C38 C39 122.3(4) . . ?
C39 C38 H38 118.8 . . ?
O11 C39 O12 123.4(4) . . ?
O11 C39 C38 127.0(4) . . ?
O12 C39 C38 109.6(3) . . ?
O12 C40 H40A 109.5 . . ?
O12 C40 H40B 109.5 . . ?
O12 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

_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_0693_cole
_database_code_depnum_ccdc_archive 'CCDC 1965042'
loop_
_audit_author_name
_audit_author_address
'Alexander Filatov'
;the University of Chicago
United States of America
;
_audit_update_record             
;
2019-11-11 deposited with the CCDC.	2020-01-22 downloaded from the CCDC.
;
_audit_creation_date             2018-10-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 O5'
_chemical_formula_sum            'C18 H16 O5'
_chemical_formula_weight         312.31
_chemical_absolute_configuration .
_chemical_melting_point          ?
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'

_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                   11.2987(6)
_cell_length_b                   10.6941(6)
_cell_length_c                   11.9582(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.7230(10)
_cell_angle_gamma                90
_cell_volume                     1444.79(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.81
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1409 before and 0.0424 after correction. 
The Ratio of minimum to maximum transmission is 0.9157. 
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            62679
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.820
_diffrn_reflns_theta_min         2.465
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  D8Venture
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus X-ray tube'
_diffrn_source_type              'INCOATEC ImuS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                7206
_reflns_number_total             7546
_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       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material  
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'XL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'XT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 3303 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         7546
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.039
_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)+(0.0502P)²+0.2469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0787
_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 Ternary CH refined with riding coordinates:
 C8(H8), C10(H10), C12(H12), C15(H15), C16(H16), C26(H26), C28(H28), C30(H30),
 C33(H33), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C13(H13A,H13B), C27(H27A,H27B), C31(H31A,H31B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C19(H19), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C36(H36A,H36B,H36C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.02997(12) 0.74539(14) 0.78450(13) 0.0272(3) Uani 1 1 d . . . . .
O2 O 0.04036(11) 0.54026(12) 0.81181(11) 0.0183(3) Uani 1 1 d . . . . .
O3 O 0.47850(11) 0.50145(13) 0.69092(11) 0.0215(3) Uani 1 1 d . . . . .
O4 O 0.11251(15) 0.47956(16) 0.53582(13) 0.0340(4) Uani 1 1 d . . . . .
O5 O 0.05704(12) 0.30615(14) 0.62626(11) 0.0253(3) Uani 1 1 d . . . . .
C1 C 0.29353(15) 0.79136(17) 1.02604(14) 0.0171(3) Uani 1 1 d . . . . .
H1 H 0.347282 0.830142 0.976390 0.021 Uiso 1 1 calc R . . . .
C2 C 0.25683(16) 0.85301(18) 1.12203(15) 0.0205(3) Uani 1 1 d . . . . .
H2 H 0.286955 0.933806 1.139149 0.025 Uiso 1 1 calc R . . . .
C3 C 0.17577(16) 0.79632(19) 1.19329(15) 0.0212(3) Uani 1 1 d . . . . .
H3 H 0.150131 0.839640 1.257976 0.025 Uiso 1 1 calc R . . . .
C4 C 0.13221(15) 0.67739(18) 1.17069(14) 0.0194(3) Uani 1 1 d . . . . .
H4 H 0.077136 0.639298 1.219458 0.023 Uiso 1 1 calc R . . . .
C5 C 0.17035(15) 0.61463(16) 1.07550(14) 0.0159(3) Uani 1 1 d . . . . .
C6 C 0.25023(14) 0.67201(16) 1.00398(13) 0.0140(3) Uani 1 1 d . . . . .
C7 C 0.27458(14) 0.59216(15) 0.90321(13) 0.0130(3) Uani 1 1 d . . . . .
C8 C 0.20658(14) 0.46770(16) 0.92569(14) 0.0146(3) Uani 1 1 d . . . . .
H8 H 0.265251 0.398329 0.934855 0.017 Uiso 1 1 calc R . . . .
C9 C 0.13891(15) 0.48434(17) 1.03684(15) 0.0180(3) Uani 1 1 d . . . . .
H9A H 0.052482 0.476189 1.024290 0.022 Uiso 1 1 calc R . . . .
H9B H 0.164703 0.421324 1.092690 0.022 Uiso 1 1 calc R . . . .
C10 C 0.12639(15) 0.43922(15) 0.82524(14) 0.0161(3) Uani 1 1 d . . . . .
H10 H 0.084210 0.358217 0.837279 0.019 Uiso 1 1 calc R . . . .
C11 C 0.09058(15) 0.65414(17) 0.79517(14) 0.0173(3) Uani 1 1 d . . . . .
C12 C 0.22329(14) 0.64958(15) 0.79291(13) 0.0136(3) Uani 1 1 d . . . . .
H12 H 0.256811 0.734795 0.779813 0.016 Uiso 1 1 calc R . . . .
C13 C 0.40411(14) 0.56918(16) 0.87173(14) 0.0146(3) Uani 1 1 d . . . . .
H13A H 0.452506 0.645184 0.884278 0.018 Uiso 1 1 calc R . . . .
H13B H 0.438444 0.499503 0.915951 0.018 Uiso 1 1 calc R . . . .
C14 C 0.39770(15) 0.53611(16) 0.74814(14) 0.0155(3) Uani 1 1 d . . . . .
C15 C 0.27045(15) 0.55561(16) 0.70630(14) 0.0150(3) Uani 1 1 d . . . . .
H15 H 0.267218 0.589855 0.628508 0.018 Uiso 1 1 calc R . . . .
C16 C 0.19891(15) 0.43230(16) 0.71734(14) 0.0161(3) Uani 1 1 d . . . . .
H16 H 0.255558 0.360704 0.723427 0.019 Uiso 1 1 calc R . . . .
C17 C 0.11844(16) 0.41190(18) 0.61552(16) 0.0203(3) Uani 1 1 d . . . . .
C18 C -0.02096(19) 0.2765(3) 0.53242(18) 0.0349(5) Uani 1 1 d . . . . .
H18A H 0.023435 0.281448 0.462681 0.052 Uiso 1 1 calc GR . . . .
H18B H -0.086619 0.336357 0.529833 0.052 Uiso 1 1 calc GR . . . .
H18C H -0.052313 0.191708 0.541449 0.052 Uiso 1 1 calc GR . . . .
O6 O 0.44708(11) 0.34639(12) 0.10639(10) 0.0178(2) Uani 1 1 d . . . . .
O7 O 0.51193(10) 0.32464(11) 0.28113(10) 0.0144(2) Uani 1 1 d . . . . .
O8 O 0.30594(11) 0.70359(12) 0.45491(10) 0.0193(3) Uani 1 1 d . . . . .
O9 O 0.30072(12) 0.24104(12) 0.50483(11) 0.0206(3) Uani 1 1 d . . . . .
O10 O 0.26842(11) 0.27273(12) 0.32155(10) 0.0198(3) Uani 1 1 d . . . . .
C19 C 0.62182(15) 0.66277(16) 0.09461(14) 0.0149(3) Uani 1 1 d . . . . .
H19 H 0.551698 0.704738 0.071119 0.018 Uiso 1 1 calc R . . . .
C20 C 0.72034(16) 0.65879(17) 0.02598(14) 0.0180(3) Uani 1 1 d . . . . .
H20 H 0.717494 0.698200 -0.045197 0.022 Uiso 1 1 calc R . . . .
C21 C 0.82278(16) 0.59761(17) 0.06084(16) 0.0202(3) Uani 1 1 d . . . . .
H21 H 0.889533 0.596208 0.013338 0.024 Uiso 1 1 calc R . . . .
C22 C 0.82901(15) 0.53849(17) 0.16410(16) 0.0193(3) Uani 1 1 d . . . . .
H22 H 0.899076 0.496169 0.187206 0.023 Uiso 1 1 calc R . . . .
C23 C 0.73070(14) 0.54227(15) 0.23331(14) 0.0149(3) Uani 1 1 d . . . . .
C24 C 0.62814(14) 0.60411(15) 0.19815(13) 0.0129(3) Uani 1 1 d . . . . .
C25 C 0.53017(14) 0.59023(15) 0.28102(13) 0.0117(3) Uani 1 1 d . . . . .
C26 C 0.58589(14) 0.50924(15) 0.37761(13) 0.0123(3) Uani 1 1 d . . . . .
H26 H 0.582458 0.557208 0.449285 0.015 Uiso 1 1 calc R . . . .
C27 C 0.71708(14) 0.48582(16) 0.34771(13) 0.0150(3) Uani 1 1 d . . . . .
H27A H 0.770751 0.526871 0.402529 0.018 Uiso 1 1 calc R . . . .
H27B H 0.734705 0.395154 0.346366 0.018 Uiso 1 1 calc R . . . .
C28 C 0.51335(14) 0.39005(15) 0.38869(13) 0.0131(3) Uani 1 1 d . . . . .
H28 H 0.549352 0.335133 0.447635 0.016 Uiso 1 1 calc R . . . .
C29 C 0.45715(14) 0.39016(15) 0.19870(13) 0.0133(3) Uani 1 1 d . . . . .
C30 C 0.42057(13) 0.51880(15) 0.23316(13) 0.0116(3) Uani 1 1 d . . . . .
H30 H 0.384120 0.565208 0.168821 0.014 Uiso 1 1 calc R . . . .
C31 C 0.47074(14) 0.70823(15) 0.32570(14) 0.0141(3) Uani 1 1 d . . . . .
H31A H 0.522802 0.752786 0.379680 0.017 Uiso 1 1 calc R . . . .
H31B H 0.448094 0.765862 0.264279 0.017 Uiso 1 1 calc R . . . .
C32 C 0.36247(14) 0.65457(16) 0.38257(13) 0.0138(3) Uani 1 1 d . . . . .
C33 C 0.33907(14) 0.52194(15) 0.33587(13) 0.0126(3) Uani 1 1 d . . . . .
H33 H 0.254013 0.508919 0.314861 0.015 Uiso 1 1 calc R . . . .
C34 C 0.38448(14) 0.42270(15) 0.41984(13) 0.0131(3) Uani 1 1 d . . . . .
H34 H 0.384856 0.460179 0.496454 0.016 Uiso 1 1 calc R . . . .
C35 C 0.31228(14) 0.30348(15) 0.42202(14) 0.0148(3) Uani 1 1 d . . . . .
C36 C 0.22039(17) 0.14750(18) 0.31296(17) 0.0239(4) Uani 1 1 d . . . . .
H36A H 0.184625 0.135699 0.238620 0.036 Uiso 1 1 calc GR . . . .
H36B H 0.160002 0.135690 0.370117 0.036 Uiso 1 1 calc GR . . . .
H36C H 0.284030 0.086378 0.324328 0.036 Uiso 1 1 calc GR . . . .


_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 C11 1.198(2) . ?
O2 C10 1.461(2) . ?
O2 C11 1.359(2) . ?
O3 C14 1.206(2) . ?
O4 C17 1.198(3) . ?
O5 C17 1.334(2) . ?
O5 C18 1.453(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.391(2) . ?
C1 C6 1.391(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(2) . ?
C5 C6 1.394(2) . ?
C5 C9 1.509(2) . ?
C6 C7 1.505(2) . ?
C7 C8 1.562(2) . ?
C7 C12 1.560(2) . ?
C7 C13 1.536(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.552(2) . ?
C8 C10 1.526(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10 1.0000 . ?
C10 C16 1.539(2) . ?
C11 C12 1.501(2) . ?
C12 H12 1.0000 . ?
C12 C15 1.543(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.520(2) . ?
C14 C15 1.531(2) . ?
C15 H15 1.0000 . ?
C15 C16 1.553(2) . ?
C16 H16 1.0000 . ?
C16 C17 1.526(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O6 C29 1.203(2) . ?
O7 C28 1.4640(19) . ?
O7 C29 1.353(2) . ?
O8 C32 1.202(2) . ?
O9 C35 1.203(2) . ?
O10 C35 1.335(2) . ?
O10 C36 1.448(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.392(2) . ?
C19 C24 1.389(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.394(2) . ?
C23 C24 1.395(2) . ?
C23 C27 1.505(2) . ?
C24 C25 1.502(2) . ?
C25 C26 1.569(2) . ?
C25 C30 1.558(2) . ?
C25 C31 1.529(2) . ?
C26 H26 1.0000 . ?
C26 C27 1.550(2) . ?
C26 C28 1.522(2) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28 1.0000 . ?
C28 C34 1.547(2) . ?
C29 C30 1.496(2) . ?
C30 H30 1.0000 . ?
C30 C33 1.545(2) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.520(2) . ?
C32 C33 1.546(2) . ?
C33 H33 1.0000 . ?
C33 C34 1.544(2) . ?
C34 H34 1.0000 . ?
C34 C35 1.514(2) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 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
C11 O2 C10 113.60(13) . . ?
C17 O5 C18 114.95(17) . . ?
C2 C1 H1 120.5 . . ?
C6 C1 H1 120.5 . . ?
C6 C1 C2 118.91(16) . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.13(17) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.79(17) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.16(16) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C9 128.36(16) . . ?
C6 C5 C4 119.89(16) . . ?
C6 C5 C9 111.74(15) . . ?
C1 C6 C5 121.10(16) . . ?
C1 C6 C7 127.23(15) . . ?
C5 C6 C7 111.58(15) . . ?
C6 C7 C8 104.50(13) . . ?
C6 C7 C12 112.58(13) . . ?
C6 C7 C13 118.13(13) . . ?
C12 C7 C8 107.62(13) . . ?
C13 C7 C8 112.22(13) . . ?
C13 C7 C12 101.58(12) . . ?
C7 C8 H8 108.9 . . ?
C9 C8 C7 107.36(13) . . ?
C9 C8 H8 108.9 . . ?
C10 C8 C7 108.85(13) . . ?
C10 C8 H8 108.9 . . ?
C10 C8 C9 113.77(14) . . ?
C5 C9 C8 104.57(13) . . ?
C5 C9 H9A 110.8 . . ?
C5 C9 H9B 110.8 . . ?
C8 C9 H9A 110.8 . . ?
C8 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
O2 C10 C8 109.05(13) . . ?
O2 C10 H10 109.8 . . ?
O2 C10 C16 107.70(13) . . ?
C8 C10 H10 109.8 . . ?
C8 C10 C16 110.64(14) . . ?
C16 C10 H10 109.8 . . ?
O1 C11 O2 120.42(16) . . ?
O1 C11 C12 126.47(17) . . ?
O2 C11 C12 113.11(14) . . ?
C7 C12 H12 110.7 . . ?
C11 C12 C7 110.98(13) . . ?
C11 C12 H12 110.7 . . ?
C11 C12 C15 112.76(13) . . ?
C15 C12 C7 100.57(12) . . ?
C15 C12 H12 110.7 . . ?
C7 C13 H13A 111.0 . . ?
C7 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
C14 C13 C7 103.99(13) . . ?
C14 C13 H13A 111.0 . . ?
C14 C13 H13B 111.0 . . ?
O3 C14 C13 126.57(16) . . ?
O3 C14 C15 124.82(16) . . ?
C13 C14 C15 108.61(13) . . ?
C12 C15 H15 112.2 . . ?
C12 C15 C16 108.14(13) . . ?
C14 C15 C12 101.55(13) . . ?
C14 C15 H15 112.2 . . ?
C14 C15 C16 110.14(14) . . ?
C16 C15 H15 112.2 . . ?
C10 C16 C15 108.28(13) . . ?
C10 C16 H16 108.8 . . ?
C15 C16 H16 108.8 . . ?
C17 C16 C10 110.96(14) . . ?
C17 C16 C15 111.04(14) . . ?
C17 C16 H16 108.8 . . ?
O4 C17 O5 124.39(17) . . ?
O4 C17 C16 125.12(17) . . ?
O5 C17 C16 110.47(16) . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
O5 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C29 O7 C28 113.11(12) . . ?
C35 O10 C36 115.22(14) . . ?
C20 C19 H19 120.7 . . ?
C24 C19 H19 120.7 . . ?
C24 C19 C20 118.64(16) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.47(16) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 120.94(16) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 H22 120.6 . . ?
C21 C22 C23 118.89(16) . . ?
C23 C22 H22 120.6 . . ?
C22 C23 C24 120.00(15) . . ?
C22 C23 C27 128.27(15) . . ?
C24 C23 C27 111.73(14) . . ?
C19 C24 C23 121.08(15) . . ?
C19 C24 C25 127.06(14) . . ?
C23 C24 C25 111.75(14) . . ?
C24 C25 C26 104.36(12) . . ?
C24 C25 C30 113.26(12) . . ?
C24 C25 C31 118.65(13) . . ?
C30 C25 C26 108.03(13) . . ?
C31 C25 C26 111.85(13) . . ?
C31 C25 C30 100.52(12) . . ?
C25 C26 H26 109.2 . . ?
C27 C26 C25 107.18(12) . . ?
C27 C26 H26 109.2 . . ?
C28 C26 C25 108.35(12) . . ?
C28 C26 H26 109.2 . . ?
C28 C26 C27 113.73(13) . . ?
C23 C27 C26 104.71(13) . . ?
C23 C27 H27A 110.8 . . ?
C23 C27 H27B 110.8 . . ?
C26 C27 H27A 110.8 . . ?
C26 C27 H27B 110.8 . . ?
H27A C27 H27B 108.9 . . ?
O7 C28 C26 108.88(12) . . ?
O7 C28 H28 109.8 . . ?
O7 C28 C34 108.62(12) . . ?
C26 C28 H28 109.8 . . ?
C26 C28 C34 109.96(13) . . ?
C34 C28 H28 109.8 . . ?
O6 C29 O7 120.27(15) . . ?
O6 C29 C30 125.97(15) . . ?
O7 C29 C30 113.65(13) . . ?
C25 C30 H30 110.9 . . ?
C29 C30 C25 109.33(13) . . ?
C29 C30 H30 110.9 . . ?
C29 C30 C33 114.12(13) . . ?
C33 C30 C25 100.15(12) . . ?
C33 C30 H30 110.9 . . ?
C25 C31 H31A 111.4 . . ?
C25 C31 H31B 111.4 . . ?
H31A C31 H31B 109.3 . . ?
C32 C31 C25 101.79(13) . . ?
C32 C31 H31A 111.4 . . ?
C32 C31 H31B 111.4 . . ?
O8 C32 C31 126.54(16) . . ?
O8 C32 C33 124.76(15) . . ?
C31 C32 C33 108.65(13) . . ?
C30 C33 C32 101.90(12) . . ?
C30 C33 H33 112.2 . . ?
C32 C33 H33 112.2 . . ?
C34 C33 C30 107.79(12) . . ?
C34 C33 C32 109.99(12) . . ?
C34 C33 H33 112.2 . . ?
C28 C34 H34 108.5 . . ?
C33 C34 C28 107.73(12) . . ?
C33 C34 H34 108.5 . . ?
C35 C34 C28 108.85(13) . . ?
C35 C34 C33 114.53(13) . . ?
C35 C34 H34 108.5 . . ?
O9 C35 O10 124.14(16) . . ?
O9 C35 C34 123.08(15) . . ?
O10 C35 C34 112.70(14) . . ?
O10 C36 H36A 109.5 . . ?
O10 C36 H36B 109.5 . . ?
O10 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

_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_0683_cole
_database_code_depnum_ccdc_archive 'CCDC 1965038'
loop_
_audit_author_name
_audit_author_address
'Alexander Filatov'
;the University of Chicago
United States of America
;
_audit_update_record             
;
2019-11-11 deposited with the CCDC.	2020-01-22 downloaded from the CCDC.
;
_audit_creation_date             2018-10-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 O7'
_chemical_formula_sum            'C18 H18 O7'
_chemical_formula_weight         346.32
_chemical_melting_point          ?
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.6526(8)
_cell_length_b                   9.7720(5)
_cell_length_c                   24.8831(13)
_cell_angle_alpha                90
_cell_angle_beta                 101.015(2)
_cell_angle_gamma                90
_cell_volume                     3258.6(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9831
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.65
_cell_measurement_theta_min      2.58
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1369 before and 0.0507 after correction. 
The Ratio of minimum to maximum transmission is 0.8892. 
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.171
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            45288
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        24.145
_diffrn_reflns_theta_max         24.145
_diffrn_reflns_theta_min         2.245
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus X-ray tube'
_diffrn_source_type              'INCOATEC ImuS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4550
_reflns_number_total             5139
_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       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material  
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'XL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'XT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         5139
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0386P)²+1.7621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0885
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C36A) = Uanis(C36B)
3. Rigid body (RIGU) restrains
 C27, C32, O13A, O14A, C33A, C34A, C35A, C36A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H32C)=Sof(H32D)=Sof(O13B)=Sof(O14B)=Sof(C33B)=Sof(H33B)=Sof(C34B)=
 Sof(H34B)=Sof(C35B)=Sof(C36B)=Sof(H36D)=Sof(H36E)=Sof(H36F)=1-FVAR(1)
 Sof(H32A)=Sof(H32B)=Sof(O13A)=Sof(O14A)=Sof(C33A)=Sof(H33A)=Sof(C34A)=
 Sof(H34A)=Sof(C35A)=Sof(C36A)=Sof(H36A)=Sof(H36B)=Sof(H36C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C23(H23), C25(H25)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C14(H14A,H14B), C26(H26A,H26B), C32(H32A,H32B), C32(H32C,H32D)
5.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C22(H22), C29(H29),
 C30(H30), C31(H31), C33A(H33A), C34A(H34A), C33B(H33B), C34B(H34B)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C36A(H36A,H36B,
 H36C), C36B(H36D,H36E,H36F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.32950(9) 0.28726(11) 0.86597(5) 0.0290(3) Uani 1 1 d . . . . .
O2 O 0.32131(11) 0.05755(12) 0.86793(5) 0.0416(3) Uani 1 1 d . . . . .
O3 O 0.50094(8) 0.05521(11) 0.75207(4) 0.0241(3) Uani 1 1 d . . . . .
O4 O 0.58805(8) 0.20004(12) 0.71092(5) 0.0274(3) Uani 1 1 d . . . . .
O5 O 0.43516(9) 0.03818(12) 0.62356(5) 0.0308(3) Uani 1 1 d . . . . .
O6 O -0.00995(9) 0.00806(12) 0.57871(5) 0.0319(3) Uani 1 1 d . . . . .
O7 O -0.09140(9) 0.19808(13) 0.54566(5) 0.0344(3) Uani 1 1 d . . . . .
C1 C 0.28791(17) 0.2926(2) 0.91496(8) 0.0421(5) Uani 1 1 d . . . . .
H1A H 0.227117 0.236917 0.909936 0.063 Uiso 1 1 calc GR . . . .
H1B H 0.271704 0.387546 0.922386 0.063 Uiso 1 1 calc GR . . . .
H1C H 0.336609 0.256805 0.945870 0.063 Uiso 1 1 calc GR . . . .
C2 C 0.34139(13) 0.16179(17) 0.84661(7) 0.0264(4) Uani 1 1 d . . . . .
C3 C 0.37884(12) 0.16760(16) 0.79491(7) 0.0230(4) Uani 1 1 d . . . . .
C4 C 0.38589(11) 0.27942(16) 0.76559(7) 0.0222(4) Uani 1 1 d . . . . .
H4 H 0.374735 0.369002 0.777979 0.027 Uiso 1 1 calc R . . . .
C5 C 0.41320(11) 0.25090(16) 0.71092(6) 0.0212(3) Uani 1 1 d . . . . .
H5 H 0.420946 0.337311 0.690609 0.025 Uiso 1 1 calc R . . . .
C6 C 0.50932(12) 0.17026(16) 0.72299(6) 0.0217(4) Uani 1 1 d . . . . .
C7 C 0.40194(12) 0.03940(16) 0.76650(7) 0.0240(4) Uani 1 1 d . . . . .
H7 H 0.400441 -0.042293 0.790537 0.029 Uiso 1 1 calc R . . . .
C8 C 0.32661(12) 0.02373(16) 0.71293(7) 0.0234(4) Uani 1 1 d . . . . .
H8A H 0.258788 0.010778 0.720748 0.028 Uiso 1 1 calc R . . . .
H8B H 0.343462 -0.057535 0.692737 0.028 Uiso 1 1 calc R . . . .
C9 C 0.32936(12) 0.15509(16) 0.67753(7) 0.0214(4) Uani 1 1 d . . . . .
C10 C 0.35532(12) 0.12415(16) 0.62279(7) 0.0230(4) Uani 1 1 d . . . . .
C11 C 0.32043(13) 0.16585(18) 0.57131(7) 0.0314(4) Uani 1 1 d . . . . .
H11 H 0.266021 0.226293 0.559638 0.038 Uiso 1 1 calc R . . . .
C12 C 0.38056(14) 0.1022(2) 0.53741(8) 0.0375(5) Uani 1 1 d . . . . .
H12 H 0.373475 0.110870 0.498830 0.045 Uiso 1 1 calc R . . . .
C13 C 0.44876(15) 0.0280(2) 0.57068(8) 0.0372(5) Uani 1 1 d . . . . .
H13 H 0.499605 -0.024511 0.559204 0.045 Uiso 1 1 calc R . . . .
C14 C 0.23000(11) 0.23450(16) 0.66950(7) 0.0228(4) Uani 1 1 d . . . . .
H14A H 0.215240 0.256756 0.705947 0.027 Uiso 1 1 calc R . . . .
H14B H 0.238198 0.321991 0.650790 0.027 Uiso 1 1 calc R . . . .
C15 C 0.14260(12) 0.15946(16) 0.63711(6) 0.0232(4) Uani 1 1 d . . . . .
H15 H 0.143448 0.062304 0.638520 0.028 Uiso 1 1 calc R . . . .
C16 C 0.06420(12) 0.21953(17) 0.60663(7) 0.0238(4) Uani 1 1 d . . . . .
H16 H 0.062564 0.316694 0.605542 0.029 Uiso 1 1 calc R . . . .
C17 C -0.02038(12) 0.14453(17) 0.57441(7) 0.0245(4) Uani 1 1 d . . . . .
C18 C -0.08769(14) -0.07180(19) 0.54565(8) 0.0364(4) Uani 1 1 d . . . . .
H18A H -0.099520 -0.038019 0.507878 0.055 Uiso 1 1 calc GR . . . .
H18B H -0.149169 -0.063653 0.560292 0.055 Uiso 1 1 calc GR . . . .
H18C H -0.067235 -0.168006 0.546306 0.055 Uiso 1 1 calc GR . . . .
O8 O 0.24652(9) 0.20866(12) 0.11435(5) 0.0283(3) Uani 1 1 d . . . . .
O9 O 0.23088(9) 0.43828(12) 0.11161(5) 0.0308(3) Uani 1 1 d . . . . .
O10 O 0.47916(8) 0.47521(11) 0.22738(5) 0.0259(3) Uani 1 1 d . . . . .
O11 O 0.61202(8) 0.35738(13) 0.26781(5) 0.0331(3) Uani 1 1 d . . . . .
O12 O 0.49194(10) 0.28707(12) 0.38867(5) 0.0354(3) Uani 1 1 d . . . . .
C19 C 0.18374(13) 0.20375(19) 0.06080(7) 0.0324(4) Uani 1 1 d . . . . .
H19A H 0.216763 0.251345 0.034505 0.049 Uiso 1 1 calc GR . . . .
H19B H 0.119902 0.248406 0.061949 0.049 Uiso 1 1 calc GR . . . .
H19C H 0.171853 0.108150 0.049518 0.049 Uiso 1 1 calc GR . . . .
C20 C 0.26720(12) 0.33527(17) 0.13379(7) 0.0247(4) Uani 1 1 d . . . . .
C21 C 0.33992(12) 0.33439(16) 0.18594(7) 0.0229(4) Uani 1 1 d . . . . .
C22 C 0.38112(12) 0.22620(16) 0.21377(7) 0.0221(4) Uani 1 1 d . . . . .
H22 H 0.370264 0.134793 0.201021 0.027 Uiso 1 1 calc R . . . .
C23 C 0.44674(12) 0.26312(16) 0.26757(6) 0.0215(4) Uani 1 1 d . . . . .
H23 H 0.479249 0.180586 0.287046 0.026 Uiso 1 1 calc R . . . .
C24 C 0.52266(12) 0.36475(17) 0.25519(6) 0.0242(4) Uani 1 1 d . . . . .
C25 C 0.36992(12) 0.46730(17) 0.21486(7) 0.0244(4) Uani 1 1 d . . . . .
H25 H 0.341114 0.546657 0.191759 0.029 Uiso 1 1 calc R . . . .
C26 C 0.33368(12) 0.46681(16) 0.26931(7) 0.0246(4) Uani 1 1 d . . . . .
H26A H 0.260079 0.458611 0.262680 0.030 Uiso 1 1 calc R . . . .
H26B H 0.352869 0.553307 0.289273 0.030 Uiso 1 1 calc R . . . .
C27 C 0.38217(12) 0.34376(16) 0.30357(7) 0.0227(4) Uani 1 1 d . U . . .
C28 C 0.44899(12) 0.39102(17) 0.35508(7) 0.0256(4) Uani 1 1 d . . . . .
C29 C 0.47596(13) 0.51282(18) 0.37871(7) 0.0296(4) Uani 1 1 d . . . . .
H29 H 0.456293 0.600559 0.364073 0.035 Uiso 1 1 calc R . . . .
C30 C 0.53992(15) 0.4846(2) 0.43006(8) 0.0392(5) Uani 1 1 d . . . . .
H30 H 0.571442 0.549711 0.456051 0.047 Uiso 1 1 calc R . . . .
C31 C 0.54659(16) 0.3484(2) 0.43428(8) 0.0434(5) Uani 1 1 d . . . . .
H31 H 0.584008 0.300670 0.464666 0.052 Uiso 1 1 calc R . . . .
C32 C 0.30273(13) 0.24411(17) 0.31815(7) 0.0288(4) Uani 1 1 d . U . . .
H32A H 0.247767 0.233294 0.286145 0.035 Uiso 0.635(8) 1 calc R . P A 1
H32B H 0.333276 0.153131 0.327334 0.035 Uiso 0.635(8) 1 calc R . P A 1
H32C H 0.271185 0.193696 0.284804 0.035 Uiso 0.365(8) 1 calc R . P A 2
H32D H 0.336011 0.176399 0.345190 0.035 Uiso 0.365(8) 1 calc R . P A 2
O13A O 0.0405(4) 0.4451(7) 0.3994(3) 0.0422(12) Uani 0.635(8) 1 d . U P A 1
O14A O 0.1871(4) 0.4069(6) 0.4543(2) 0.0279(11) Uani 0.635(8) 1 d . U P A 1
C33A C 0.2607(4) 0.2993(3) 0.3673(2) 0.0245(9) Uani 0.635(8) 1 d . U P A 1
H33A H 0.302231 0.299395 0.402559 0.029 Uiso 0.635(8) 1 calc R . P A 1
C34A C 0.1690(3) 0.3463(3) 0.36161(13) 0.0268(11) Uani 0.635(8) 1 d . U P A 1
H34A H 0.128488 0.341828 0.326069 0.032 Uiso 0.635(8) 1 calc R . P A 1
C35A C 0.1236(6) 0.4049(9) 0.4054(4) 0.0268(19) Uani 0.635(8) 1 d . U P A 1
C36A C 0.1480(6) 0.4689(12) 0.4991(4) 0.0407(17) Uani 0.635(8) 1 d . U P A 1
H36A H 0.124417 0.561643 0.488754 0.061 Uiso 0.635(8) 1 calc GR . P A 1
H36B H 0.200877 0.472947 0.531803 0.061 Uiso 0.635(8) 1 calc GR . P A 1
H36C H 0.092437 0.413653 0.506895 0.061 Uiso 0.635(8) 1 calc GR . P A 1
O13B O 0.0807(8) 0.4457(13) 0.3949(4) 0.039(3) Uani 0.365(8) 1 d . . P A 2
O14B O 0.1888(9) 0.3974(13) 0.4749(4) 0.031(2) Uani 0.365(8) 1 d . . P A 2
C33B C 0.2241(5) 0.3164(5) 0.3411(3) 0.0205(18) Uani 0.365(8) 1 d . . P A 2
H33B H 0.169890 0.359487 0.317552 0.025 Uiso 0.365(8) 1 calc R . P A 2
C34B C 0.2309(5) 0.3197(6) 0.3948(3) 0.0285(19) Uani 0.365(8) 1 d . . P A 2
H34B H 0.284323 0.273105 0.417542 0.034 Uiso 0.365(8) 1 calc R . P A 2
C35B C 0.1570(9) 0.3944(16) 0.4204(6) 0.020(3) Uani 0.365(8) 1 d . . P A 2
C36B C 0.1182(13) 0.463(2) 0.5023(9) 0.0407(17) Uani 0.365(8) 1 d . . P A 2
H36D H 0.104269 0.555392 0.487521 0.061 Uiso 0.365(8) 1 calc GR . P A 2
H36E H 0.145739 0.468480 0.541593 0.061 Uiso 0.365(8) 1 calc GR . P A 2
H36F H 0.056168 0.409784 0.496455 0.061 Uiso 0.365(8) 1 calc GR . 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 C1 1.441(2) . ?
O1 C2 1.338(2) . ?
O2 C2 1.204(2) . ?
O3 C6 1.354(2) . ?
O3 C7 1.471(2) . ?
O4 C6 1.2056(19) . ?
O5 C10 1.3735(19) . ?
O5 C13 1.367(2) . ?
O6 C17 1.343(2) . ?
O6 C18 1.442(2) . ?
O7 C17 1.209(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.474(2) . ?
C3 C4 1.328(2) . ?
C3 C7 1.501(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.504(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.511(2) . ?
C5 C9 1.585(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.528(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.561(2) . ?
C9 C10 1.502(2) . ?
C9 C14 1.542(2) . ?
C10 C11 1.342(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.427(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.335(3) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.498(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.325(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.470(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O8 C19 1.441(2) . ?
O8 C20 1.339(2) . ?
O9 C20 1.208(2) . ?
O10 C24 1.356(2) . ?
O10 C25 1.466(2) . ?
O11 C24 1.202(2) . ?
O12 C28 1.374(2) . ?
O12 C31 1.371(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.476(2) . ?
C21 C22 1.329(2) . ?
C21 C25 1.503(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.506(2) . ?
C23 H23 1.0000 . ?
C23 C24 1.509(2) . ?
C23 C27 1.582(2) . ?
C25 H25 1.0000 . ?
C25 C26 1.529(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.548(2) . ?
C27 C28 1.497(2) . ?
C27 C32 1.551(2) . ?
C28 C29 1.347(2) . ?
C29 H29 0.9500 . ?
C29 C30 1.430(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.337(3) . ?
C31 H31 0.9500 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 H32C 0.9900 . ?
C32 H32D 0.9900 . ?
C32 C33A 1.543(5) . ?
C32 C33B 1.487(7) . ?
O13A C35A 1.183(10) . ?
O14A C35A 1.353(7) . ?
O14A C36A 1.456(10) . ?
C33A H33A 0.9500 . ?
C33A C34A 1.316(8) . ?
C34A H34A 0.9500 . ?
C34A C35A 1.468(10) . ?
C36A H36A 0.9800 . ?
C36A H36B 0.9800 . ?
C36A H36C 0.9800 . ?
O13B C35B 1.220(13) . ?
O14B C35B 1.343(11) . ?
O14B C36B 1.434(19) . ?
C33B H33B 0.9500 . ?
C33B C34B 1.322(13) . ?
C34B H34B 0.9500 . ?
C34B C35B 1.484(15) . ?
C36B H36D 0.9800 . ?
C36B H36E 0.9800 . ?
C36B H36F 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
C2 O1 C1 115.59(13) . . ?
C6 O3 C7 113.14(12) . . ?
C13 O5 C10 106.52(13) . . ?
C17 O6 C18 115.90(14) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 111.41(14) . . ?
O2 C2 O1 124.26(15) . . ?
O2 C2 C3 124.29(15) . . ?
C2 C3 C7 121.20(14) . . ?
C4 C3 C2 125.82(15) . . ?
C4 C3 C7 112.60(14) . . ?
C3 C4 H4 123.2 . . ?
C3 C4 C5 113.65(14) . . ?
C5 C4 H4 123.2 . . ?
C4 C5 H5 111.7 . . ?
C4 C5 C6 105.84(13) . . ?
C4 C5 C9 107.73(12) . . ?
C6 C5 H5 111.7 . . ?
C6 C5 C9 107.99(13) . . ?
C9 C5 H5 111.7 . . ?
O3 C6 C5 112.37(13) . . ?
O4 C6 O3 120.27(14) . . ?
O4 C6 C5 127.33(15) . . ?
O3 C7 C3 108.22(13) . . ?
O3 C7 H7 110.8 . . ?
O3 C7 C8 107.11(13) . . ?
C3 C7 H7 110.8 . . ?
C3 C7 C8 109.12(13) . . ?
C8 C7 H7 110.8 . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
C7 C8 C9 108.97(13) . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
C8 C9 C5 106.42(12) . . ?
C10 C9 C5 108.80(13) . . ?
C10 C9 C8 112.42(13) . . ?
C10 C9 C14 109.74(13) . . ?
C14 C9 C5 107.44(12) . . ?
C14 C9 C8 111.80(13) . . ?
O5 C10 C9 115.76(13) . . ?
C11 C10 O5 109.57(14) . . ?
C11 C10 C9 134.61(15) . . ?
C10 C11 H11 126.5 . . ?
C10 C11 C12 107.01(16) . . ?
C12 C11 H11 126.5 . . ?
C11 C12 H12 126.8 . . ?
C13 C12 C11 106.37(16) . . ?
C13 C12 H12 126.8 . . ?
O5 C13 H13 124.7 . . ?
C12 C13 O5 110.51(16) . . ?
C12 C13 H13 124.7 . . ?
C9 C14 H14A 108.6 . . ?
C9 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 C9 114.45(13) . . ?
C15 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C14 C15 H15 117.8 . . ?
C16 C15 C14 124.36(15) . . ?
C16 C15 H15 117.8 . . ?
C15 C16 H16 118.1 . . ?
C15 C16 C17 123.78(15) . . ?
C17 C16 H16 118.1 . . ?
O6 C17 C16 113.05(14) . . ?
O7 C17 O6 122.53(15) . . ?
O7 C17 C16 124.39(15) . . ?
O6 C18 H18A 109.5 . . ?
O6 C18 H18B 109.5 . . ?
O6 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 O8 C19 114.34(13) . . ?
C24 O10 C25 113.26(12) . . ?
C31 O12 C28 106.39(14) . . ?
O8 C19 H19A 109.5 . . ?
O8 C19 H19B 109.5 . . ?
O8 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O8 C20 C21 111.87(14) . . ?
O9 C20 O8 124.41(15) . . ?
O9 C20 C21 123.72(15) . . ?
C20 C21 C25 119.47(14) . . ?
C22 C21 C20 127.57(15) . . ?
C22 C21 C25 112.87(14) . . ?
C21 C22 H22 123.4 . . ?
C21 C22 C23 113.18(14) . . ?
C23 C22 H22 123.4 . . ?
C22 C23 H23 111.8 . . ?
C22 C23 C24 106.94(13) . . ?
C22 C23 C27 108.75(13) . . ?
C24 C23 H23 111.8 . . ?
C24 C23 C27 105.46(12) . . ?
C27 C23 H23 111.8 . . ?
O10 C24 C23 112.15(13) . . ?
O11 C24 O10 120.29(15) . . ?
O11 C24 C23 127.54(16) . . ?
O10 C25 C21 108.68(13) . . ?
O10 C25 H25 110.7 . . ?
O10 C25 C26 107.47(13) . . ?
C21 C25 H25 110.7 . . ?
C21 C25 C26 108.48(13) . . ?
C26 C25 H25 110.7 . . ?
C25 C26 H26A 110.0 . . ?
C25 C26 H26B 110.0 . . ?
C25 C26 C27 108.29(13) . . ?
H26A C26 H26B 108.4 . . ?
C27 C26 H26A 110.0 . . ?
C27 C26 H26B 110.0 . . ?
C26 C27 C23 107.53(13) . . ?
C26 C27 C32 111.83(13) . . ?
C28 C27 C23 108.91(13) . . ?
C28 C27 C26 111.00(13) . . ?
C28 C27 C32 109.40(14) . . ?
C32 C27 C23 108.05(12) . . ?
O12 C28 C27 114.35(14) . . ?
C29 C28 O12 109.78(15) . . ?
C29 C28 C27 135.82(16) . . ?
C28 C29 H29 126.6 . . ?
C28 C29 C30 106.78(16) . . ?
C30 C29 H29 126.6 . . ?
C29 C30 H30 126.8 . . ?
C31 C30 C29 106.45(17) . . ?
C31 C30 H30 126.8 . . ?
O12 C31 H31 124.7 . . ?
C30 C31 O12 110.60(17) . . ?
C30 C31 H31 124.7 . . ?
C27 C32 H32A 109.6 . . ?
C27 C32 H32B 109.6 . . ?
C27 C32 H32C 109.1 . . ?
C27 C32 H32D 109.1 . . ?
H32A C32 H32B 108.1 . . ?
H32C C32 H32D 107.9 . . ?
C33A C32 C27 110.37(17) . . ?
C33A C32 H32A 109.6 . . ?
C33A C32 H32B 109.6 . . ?
C33B C32 C27 112.3(2) . . ?
C33B C32 H32C 109.1 . . ?
C33B C32 H32D 109.1 . . ?
C35A O14A C36A 115.5(7) . . ?
C32 C33A H33A 119.1 . . ?
C34A C33A C32 121.8(4) . . ?
C34A C33A H33A 119.1 . . ?
C33A C34A H34A 117.1 . . ?
C33A C34A C35A 125.8(5) . . ?
C35A C34A H34A 117.1 . . ?
O13A C35A O14A 122.8(8) . . ?
O13A C35A C34A 124.6(8) . . ?
O14A C35A C34A 112.7(6) . . ?
O14A C36A H36A 109.5 . . ?
O14A C36A H36B 109.5 . . ?
O14A C36A H36C 109.5 . . ?
H36A C36A H36B 109.5 . . ?
H36A C36A H36C 109.5 . . ?
H36B C36A H36C 109.5 . . ?
C35B O14B C36B 111.9(14) . . ?
C32 C33B H33B 120.5 . . ?
C34B C33B C32 118.9(7) . . ?
C34B C33B H33B 120.5 . . ?
C33B C34B H34B 119.2 . . ?
C33B C34B C35B 121.6(7) . . ?
C35B C34B H34B 119.2 . . ?
O13B C35B O14B 126.6(14) . . ?
O13B C35B C34B 124.2(13) . . ?
O14B C35B C34B 109.2(10) . . ?
O14B C36B H36D 109.5 . . ?
O14B C36B H36E 109.5 . . ?
O14B C36B H36F 109.5 . . ?
H36D C36B H36E 109.5 . . ?
H36D C36B H36F 109.5 . . ?
H36E C36B H36F 109.5 . . ?

_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_0737_cole
_database_code_depnum_ccdc_archive 'CCDC 1965039'
loop_
_audit_author_name
_audit_author_address
'Alexander Filatov'
;the University of Chicago
United States of America
;
_audit_update_record             
;
2019-11-11 deposited with the CCDC.	2020-01-22 downloaded from the CCDC.
;
_audit_creation_date             2019-02-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H29 N O8'
_chemical_formula_sum            'C27 H29 N O8'
_chemical_formula_weight         495.51
_chemical_absolute_configuration .
_chemical_melting_point          ?
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'

_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                   10.1038(7)
_cell_length_b                   12.0566(9)
_cell_length_c                   10.4153(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.827(2)
_cell_angle_gamma                90
_cell_volume                     1256.95(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.47
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1292 before and 0.0627 after correction. 
The Ratio of minimum to maximum transmission is 0.8445. 
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            30674
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.086
_diffrn_reflns_theta_max         25.086
_diffrn_reflns_theta_min         2.598
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus X-ray tube'
_diffrn_source_type              'INCOATEC ImuS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                3518
_reflns_number_total             4414
_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       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material  
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'XL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'XT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1368 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4414
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.059
_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)+(0.0381P)²+0.2981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0916
_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 Ternary CH refined with riding coordinates:
 C21(H21), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17), C24(H24)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C14(H14A,H14B,H14C),
 C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.5807(3) 0.1093(3) 0.2178(3) 0.0647(8) Uani 1 1 d . . . . .
O2 O 0.5832(2) 0.2743(3) 0.1198(2) 0.0533(7) Uani 1 1 d . . . . .
O3 O 0.1873(3) 0.5798(3) 0.1142(3) 0.0655(9) Uani 1 1 d . . . . .
O4 O 0.0691(2) 0.6030(3) 0.2778(2) 0.0534(7) Uani 1 1 d . . . . .
O5 O 0.0660(2) 0.7751(3) 0.6074(3) 0.0648(8) Uani 1 1 d . . . . .
O6 O 0.2740(2) 0.8346(2) 0.5918(2) 0.0488(7) Uani 1 1 d . . . . .
O7 O 0.7578(2) 0.5218(2) 0.6325(2) 0.0441(7) Uani 1 1 d . . . . .
O8 O 0.7445(2) 0.4059(2) 0.8023(2) 0.0457(7) Uani 1 1 d . . . . .
N1 N 0.5695(2) 0.4205(2) 0.6465(2) 0.0346(7) Uani 1 1 d . . . . .
C1 C 0.8710(5) 0.5597(5) 0.9115(5) 0.0871(18) Uani 1 1 d . . . . .
H1A H 0.861252 0.603949 0.831909 0.131 Uiso 1 1 calc GR . . . .
H1B H 0.954148 0.580196 0.966175 0.131 Uiso 1 1 calc GR . . . .
H1C H 0.795071 0.573766 0.958601 0.131 Uiso 1 1 calc GR . . . .
C2 C 0.8799(4) 0.3635(5) 0.9955(4) 0.0802(18) Uani 1 1 d . . . . .
H2A H 0.803745 0.379556 1.041561 0.120 Uiso 1 1 calc GR . . . .
H2B H 0.963296 0.376295 1.053553 0.120 Uiso 1 1 calc GR . . . .
H2C H 0.875891 0.285984 0.967015 0.120 Uiso 1 1 calc GR . . . .
C3 C 0.9861(3) 0.4108(4) 0.8019(4) 0.0570(12) Uani 1 1 d . . . . .
H3A H 0.976038 0.333901 0.771695 0.086 Uiso 1 1 calc GR . . . .
H3B H 1.072100 0.419356 0.857190 0.086 Uiso 1 1 calc GR . . . .
H3C H 0.982953 0.460555 0.727116 0.086 Uiso 1 1 calc GR . . . .
C4 C 0.8749(3) 0.4393(4) 0.8779(3) 0.0497(11) Uani 1 1 d . . . . .
C5 C 0.6999(3) 0.4557(3) 0.6916(3) 0.0379(9) Uani 1 1 d . . . . .
C6 C 0.4985(3) 0.4669(3) 0.5348(3) 0.0368(9) Uani 1 1 d . . . . .
H6 H 0.533612 0.519699 0.480782 0.044 Uiso 1 1 calc R . . . .
C7 C 0.3732(3) 0.4260(3) 0.5146(3) 0.0343(8) Uani 1 1 d . . . . .
C8 C 0.3622(3) 0.3460(3) 0.6166(3) 0.0350(8) Uani 1 1 d . . . . .
C9 C 0.2587(3) 0.2778(3) 0.6458(3) 0.0421(9) Uani 1 1 d . . . . .
H9 H 0.175921 0.275927 0.590233 0.051 Uiso 1 1 calc R . . . .
C10 C 0.2776(3) 0.2134(4) 0.7555(3) 0.0457(10) Uani 1 1 d . . . . .
H10 H 0.206895 0.167788 0.776275 0.055 Uiso 1 1 calc R . . . .
C11 C 0.3988(3) 0.2141(4) 0.8366(4) 0.0454(10) Uani 1 1 d . . . . .
H11 H 0.409447 0.168450 0.911631 0.055 Uiso 1 1 calc R . . . .
C12 C 0.5054(3) 0.2803(3) 0.8103(3) 0.0417(9) Uani 1 1 d . . . . .
H12 H 0.588163 0.280600 0.865879 0.050 Uiso 1 1 calc R . . . .
C13 C 0.4853(3) 0.3455(3) 0.6998(3) 0.0361(8) Uani 1 1 d . . . . .
C14 C 0.6889(5) 0.0745(5) 0.1511(5) 0.0763(15) Uani 1 1 d . . . . .
H14A H 0.663399 0.083670 0.057550 0.114 Uiso 1 1 calc GR . . . .
H14B H 0.709279 -0.003677 0.170576 0.114 Uiso 1 1 calc GR . . . .
H14C H 0.768025 0.119767 0.179781 0.114 Uiso 1 1 calc GR . . . .
C15 C 0.5352(4) 0.2122(4) 0.1915(4) 0.0460(10) Uani 1 1 d . . . . .
C16 C 0.4237(4) 0.2374(4) 0.2642(4) 0.0482(10) Uani 1 1 d . . . . .
H16 H 0.403266 0.186999 0.328813 0.058 Uiso 1 1 calc R . . . .
C17 C 0.3514(3) 0.3283(4) 0.2417(3) 0.0469(10) Uani 1 1 d . . . . .
H17 H 0.374070 0.378582 0.177915 0.056 Uiso 1 1 calc R . . . .
C18 C 0.2356(3) 0.3566(4) 0.3112(3) 0.0456(10) Uani 1 1 d . . . . .
H18A H 0.212127 0.290534 0.359938 0.055 Uiso 1 1 calc R . . . .
H18B H 0.157614 0.374830 0.246456 0.055 Uiso 1 1 calc R . . . .
C19 C 0.2632(3) 0.4557(3) 0.4071(3) 0.0395(9) Uani 1 1 d . . . . .
C20 C 0.1315(3) 0.4847(3) 0.4625(3) 0.0424(9) Uani 1 1 d . . . . .
H20A H 0.060890 0.430664 0.430305 0.051 Uiso 1 1 calc R . . . .
H20B H 0.146561 0.480623 0.558272 0.051 Uiso 1 1 calc R . . . .
C21 C 0.0872(3) 0.6011(4) 0.4198(3) 0.0463(10) Uani 1 1 d . . . . .
H21 H 0.001777 0.620470 0.452921 0.056 Uiso 1 1 calc R . . . .
C22 C 0.1845(4) 0.5833(4) 0.2289(4) 0.0534(11) Uani 1 1 d . . . . .
C23 C 0.3014(3) 0.5625(3) 0.3343(3) 0.0425(10) Uani 1 1 d . . . . .
H23 H 0.386630 0.551917 0.296938 0.051 Uiso 1 1 calc R . . . .
C24 C 0.3101(3) 0.6594(3) 0.4249(3) 0.0419(9) Uani 1 1 d . . . . .
H24 H 0.389380 0.701229 0.448091 0.050 Uiso 1 1 calc R . . . .
C25 C 0.1947(3) 0.6813(3) 0.4700(4) 0.0430(10) Uani 1 1 d . . . . .
C26 C 0.1702(3) 0.7670(4) 0.5629(4) 0.0471(10) Uani 1 1 d . . . . .
C27 C 0.2539(4) 0.9297(4) 0.6730(4) 0.0535(11) Uani 1 1 d . . . . .
H27A H 0.215341 0.990983 0.618503 0.080 Uiso 1 1 calc GR . . . .
H27B H 0.339920 0.952824 0.720536 0.080 Uiso 1 1 calc GR . . . .
H27C H 0.192992 0.909281 0.734725 0.080 Uiso 1 1 calc GR . . . .


_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 C14 1.435(5) . ?
O1 C15 1.339(5) . ?
O2 C15 1.205(4) . ?
O3 C22 1.199(5) . ?
O4 C21 1.465(4) . ?
O4 C22 1.356(5) . ?
O5 C26 1.211(4) . ?
O6 C26 1.330(5) . ?
O6 C27 1.455(5) . ?
O7 C5 1.205(4) . ?
O8 C4 1.496(4) . ?
O8 C5 1.324(4) . ?
N1 C5 1.403(4) . ?
N1 C6 1.397(4) . ?
N1 C13 1.406(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C4 1.495(7) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 C4 1.523(6) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C3 C4 1.500(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.348(4) . ?
C7 C8 1.450(5) . ?
C7 C19 1.509(5) . ?
C8 C9 1.397(5) . ?
C8 C13 1.415(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.373(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.397(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.472(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.321(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.496(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.558(6) . ?
C19 C20 1.561(4) . ?
C19 C23 1.569(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.520(6) . ?
C21 H21 1.0000 . ?
C21 C25 1.494(5) . ?
C22 C23 1.520(5) . ?
C23 H23 1.0000 . ?
C23 C24 1.497(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.341(5) . ?
C25 C26 1.460(6) . ?
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
C15 O1 C14 115.8(3) . . ?
C22 O4 C21 112.4(3) . . ?
C26 O6 C27 116.5(3) . . ?
C5 O8 C4 120.5(3) . . ?
C5 N1 C13 130.8(3) . . ?
C6 N1 C5 120.7(3) . . ?
C6 N1 C13 108.4(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
O8 C4 C2 101.1(3) . . ?
O8 C4 C3 109.3(3) . . ?
C1 C4 O8 109.6(3) . . ?
C1 C4 C2 113.1(4) . . ?
C1 C4 C3 113.1(4) . . ?
C3 C4 C2 110.0(4) . . ?
O7 C5 O8 127.8(3) . . ?
O7 C5 N1 121.9(3) . . ?
O8 C5 N1 110.3(3) . . ?
N1 C6 H6 124.8 . . ?
C7 C6 N1 110.4(3) . . ?
C7 C6 H6 124.8 . . ?
C6 C7 C8 107.0(3) . . ?
C6 C7 C19 127.6(3) . . ?
C8 C7 C19 125.4(3) . . ?
C9 C8 C7 133.3(3) . . ?
C9 C8 C13 119.1(3) . . ?
C13 C8 C7 107.6(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(3) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 120.9(3) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.5(3) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 121.4 . . ?
C13 C12 C11 117.2(3) . . ?
C13 C12 H12 121.4 . . ?
N1 C13 C8 106.5(3) . . ?
C12 C13 N1 131.7(3) . . ?
C12 C13 C8 121.9(3) . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 C16 110.6(4) . . ?
O2 C15 O1 123.1(4) . . ?
O2 C15 C16 126.3(4) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.6(4) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 118.2 . . ?
C16 C17 C18 123.6(4) . . ?
C18 C17 H17 118.2 . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
C17 C18 C19 113.6(3) . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C7 C19 C18 110.1(3) . . ?
C7 C19 C20 111.0(2) . . ?
C7 C19 C23 110.4(3) . . ?
C18 C19 C20 108.7(3) . . ?
C18 C19 C23 110.7(3) . . ?
C20 C19 C23 105.8(3) . . ?
C19 C20 H20A 109.8 . . ?
C19 C20 H20B 109.8 . . ?
H20A C20 H20B 108.3 . . ?
C21 C20 C19 109.3(3) . . ?
C21 C20 H20A 109.8 . . ?
C21 C20 H20B 109.8 . . ?
O4 C21 C20 107.5(3) . . ?
O4 C21 H21 110.4 . . ?
O4 C21 C25 109.1(3) . . ?
C20 C21 H21 110.4 . . ?
C25 C21 C20 108.9(3) . . ?
C25 C21 H21 110.4 . . ?
O3 C22 O4 121.3(4) . . ?
O3 C22 C23 126.3(4) . . ?
O4 C22 C23 112.4(3) . . ?
C19 C23 H23 111.4 . . ?
C22 C23 C19 105.5(3) . . ?
C22 C23 H23 111.4 . . ?
C24 C23 C19 109.5(3) . . ?
C24 C23 C22 107.4(3) . . ?
C24 C23 H23 111.4 . . ?
C23 C24 H24 123.3 . . ?
C25 C24 C23 113.3(3) . . ?
C25 C24 H24 123.3 . . ?
C24 C25 C21 112.0(4) . . ?
C24 C25 C26 127.3(3) . . ?
C26 C25 C21 120.6(3) . . ?
O5 C26 O6 124.4(4) . . ?
O5 C26 C25 123.0(4) . . ?
O6 C26 C25 112.6(3) . . ?
O6 C27 H27A 109.5 . . ?
O6 C27 H27B 109.5 . . ?
O6 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_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_cu_0682_cole_am_0m
_database_code_depnum_ccdc_archive 'CCDC 1965044'
loop_
_audit_author_name
_audit_author_address
'Alexander Filatov'
;the University of Chicago
United States of America
;
_audit_update_record             
;
2019-11-11 deposited with the CCDC.	2020-01-22 downloaded from the CCDC.
;
_audit_creation_date             2018-10-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H20 O6'
_chemical_formula_sum            'C17 H20 O6'
_chemical_formula_weight         320.33
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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                   7.0910(4)
_cell_length_b                   16.2621(9)
_cell_length_c                   13.2704(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.494(2)
_cell_angle_gamma                90
_cell_volume                     1528.82(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.69
_cell_measurement_theta_min      4.30
_shelx_estimated_absorpt_T_max   0.791
_shelx_estimated_absorpt_T_min   0.731
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1514 before and 0.0521 after correction. 
The Ratio of minimum to maximum transmission is 0.7074. 
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25135
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.687
_diffrn_reflns_theta_min         3.333
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus X-ray tube'
_diffrn_source_type              'INCOATEC ImuS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                5944
_reflns_number_total             6029
_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       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material  
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'XL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'XT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 2775 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         6029
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0275
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0455P)²+0.1930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0709
_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 Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C9(H9), C21(H21), C22(H22), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C27(H27A,
 H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C14(H14), C15(H15), C26(H26), C31(H31), C32(H32)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C34(H34A,H34B,H34C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.47488(19) 0.08245(9) 1.20889(9) 0.0214(3) Uani 1 1 d . . . . .
O2 O 0.59619(19) 0.16748(9) 1.32872(10) 0.0225(3) Uani 1 1 d . . . . .
O3 O 0.33200(17) 0.35687(8) 1.18837(9) 0.0179(3) Uani 1 1 d . . . . .
O4 O 0.10254(18) 0.38228(9) 1.07373(10) 0.0240(3) Uani 1 1 d . . . . .
O5 O 0.4373(2) 0.24908(9) 0.64805(10) 0.0252(3) Uani 1 1 d . . . . .
O6 O 0.4788(2) 0.11315(9) 0.66950(11) 0.0246(3) Uani 1 1 d . . . . .
C1 C 0.5084(3) 0.01440(12) 1.27763(15) 0.0263(4) Uani 1 1 d . . . . .
H1A H 0.441777 -0.034451 1.251460 0.040 Uiso 1 1 calc GR . . . .
H1B H 0.461915 0.028591 1.343903 0.040 Uiso 1 1 calc GR . . . .
H1C H 0.644046 0.002988 1.284066 0.040 Uiso 1 1 calc GR . . . .
C2 C 0.5229(2) 0.15659(12) 1.24595(13) 0.0160(3) Uani 1 1 d . . . . .
C3 C 0.4739(2) 0.22334(11) 1.17389(13) 0.0161(3) Uani 1 1 d . . . . .
C4 C 0.5115(2) 0.31185(11) 1.20085(13) 0.0161(3) Uani 1 1 d . . . . .
H4 H 0.564419 0.316676 1.271694 0.019 Uiso 1 1 calc R . . . .
C5 C 0.2491(2) 0.34803(12) 1.09535(14) 0.0170(3) Uani 1 1 d . . . . .
C6 C 0.3926(2) 0.21398(12) 1.08215(13) 0.0167(3) Uani 1 1 d . . . . .
H6 H 0.357546 0.162024 1.054488 0.020 Uiso 1 1 calc R . . . .
C7 C 0.3617(2) 0.29417(12) 1.02660(13) 0.0164(3) Uani 1 1 d . . . . .
H7 H 0.295205 0.285983 0.959344 0.020 Uiso 1 1 calc R . . . .
C8 C 0.5603(2) 0.33625(11) 1.01696(13) 0.0151(3) Uani 1 1 d . . . . .
C9 C 0.6476(2) 0.34916(11) 1.12629(13) 0.0155(3) Uani 1 1 d . . . . .
H9 H 0.772849 0.320995 1.133351 0.019 Uiso 1 1 calc R . . . .
C10 C 0.6739(3) 0.44288(11) 1.13992(14) 0.0190(4) Uani 1 1 d . . . . .
H10A H 0.641998 0.459770 1.208798 0.023 Uiso 1 1 calc R . . . .
H10B H 0.806134 0.458788 1.128839 0.023 Uiso 1 1 calc R . . . .
C11 C 0.5393(3) 0.48354(12) 1.06096(14) 0.0212(4) Uani 1 1 d . . . . .
H11A H 0.586176 0.538415 1.041583 0.025 Uiso 1 1 calc R . . . .
H11B H 0.410994 0.489384 1.086595 0.025 Uiso 1 1 calc R . . . .
C12 C 0.5400(3) 0.42343(11) 0.97146(13) 0.0186(4) Uani 1 1 d . . . . .
H12A H 0.646820 0.435577 0.928209 0.022 Uiso 1 1 calc R . . . .
H12B H 0.420872 0.428033 0.930097 0.022 Uiso 1 1 calc R . . . .
C13 C 0.6860(2) 0.28115(12) 0.95321(13) 0.0178(3) Uani 1 1 d . . . . .
H13A H 0.812640 0.306382 0.950209 0.021 Uiso 1 1 calc R . . . .
H13B H 0.701030 0.226866 0.986368 0.021 Uiso 1 1 calc R . . . .
C14 C 0.6048(2) 0.26920(12) 0.84793(13) 0.0185(4) Uani 1 1 d . . . . .
H14 H 0.573572 0.317134 0.809857 0.022 Uiso 1 1 calc R . . . .
C15 C 0.5734(3) 0.19720(12) 0.80389(14) 0.0194(4) Uani 1 1 d . . . . .
H15 H 0.604792 0.148114 0.839638 0.023 Uiso 1 1 calc R . . . .
C16 C 0.4899(3) 0.19184(12) 0.69957(14) 0.0189(4) Uani 1 1 d . . . . .
C17 C 0.3969(3) 0.10083(13) 0.56897(15) 0.0280(4) Uani 1 1 d . . . . .
H17A H 0.465954 0.133753 0.520887 0.042 Uiso 1 1 calc GR . . . .
H17B H 0.264251 0.117859 0.566885 0.042 Uiso 1 1 calc GR . . . .
H17C H 0.405109 0.042534 0.550975 0.042 Uiso 1 1 calc GR . . . .
O7 O -0.01234(19) 0.67298(9) 0.26011(10) 0.0216(3) Uani 1 1 d . . . . .
O8 O -0.08434(19) 0.79572(9) 0.19037(9) 0.0228(3) Uani 1 1 d . . . . .
O9 O 0.20822(17) 0.91285(8) 0.40980(10) 0.0183(3) Uani 1 1 d . . . . .
O10 O 0.43753(18) 0.89331(9) 0.52682(11) 0.0226(3) Uani 1 1 d . . . . .
O11 O -0.0095(2) 0.53937(9) 0.79760(10) 0.0223(3) Uani 1 1 d . . . . .
O12 O 0.0457(2) 0.66201(9) 0.87022(10) 0.0271(3) Uani 1 1 d . . . . .
C18 C -0.0597(3) 0.63445(13) 0.16393(15) 0.0259(4) Uani 1 1 d . . . . .
H18A H 0.009479 0.661605 0.110931 0.039 Uiso 1 1 calc GR . . . .
H18B H -0.195703 0.639521 0.148736 0.039 Uiso 1 1 calc GR . . . .
H18C H -0.024977 0.576148 0.167032 0.039 Uiso 1 1 calc GR . . . .
C19 C -0.0271(2) 0.75540(12) 0.26162(13) 0.0170(4) Uani 1 1 d . . . . .
C20 C 0.0372(2) 0.79019(12) 0.35961(13) 0.0161(3) Uani 1 1 d . . . . .
C21 C 0.0197(2) 0.88129(11) 0.37830(13) 0.0161(3) Uani 1 1 d . . . . .
H21 H -0.029923 0.910107 0.316074 0.019 Uiso 1 1 calc R . . . .
C22 C -0.1119(2) 0.89457(11) 0.46550(13) 0.0151(3) Uani 1 1 d . . . . .
H22 H -0.239073 0.871005 0.447095 0.018 Uiso 1 1 calc R . . . .
C23 C -0.0242(2) 0.84837(11) 0.56039(12) 0.0142(3) Uani 1 1 d . . . . .
C24 C 0.1621(2) 0.80442(11) 0.52813(13) 0.0154(3) Uani 1 1 d . . . . .
H24 H 0.224851 0.773159 0.585170 0.018 Uiso 1 1 calc R . . . .
C25 C 0.2872(2) 0.87246(11) 0.49016(13) 0.0165(3) Uani 1 1 d . . . . .
C26 C 0.1133(2) 0.74989(11) 0.43884(13) 0.0153(3) Uani 1 1 d . . . . .
H26 H 0.134817 0.692227 0.439043 0.018 Uiso 1 1 calc R . . . .
C27 C -0.1336(3) 0.98537(12) 0.49712(14) 0.0196(4) Uani 1 1 d . . . . .
H27A H -0.025761 1.018686 0.475406 0.024 Uiso 1 1 calc R . . . .
H27B H -0.252090 1.009070 0.467540 0.024 Uiso 1 1 calc R . . . .
C28 C -0.1375(3) 0.98217(12) 0.61256(14) 0.0194(4) Uani 1 1 d . . . . .
H28A H -0.102899 1.035964 0.643006 0.023 Uiso 1 1 calc R . . . .
H28B H -0.263548 0.965721 0.634783 0.023 Uiso 1 1 calc R . . . .
C29 C 0.0112(2) 0.91659(11) 0.63989(13) 0.0169(3) Uani 1 1 d . . . . .
H29A H -0.005078 0.895176 0.708798 0.020 Uiso 1 1 calc R . . . .
H29B H 0.140272 0.939298 0.636053 0.020 Uiso 1 1 calc R . . . .
C30 C -0.1622(2) 0.78260(11) 0.59716(12) 0.0158(3) Uani 1 1 d . . . . .
H30A H -0.282243 0.809600 0.613525 0.019 Uiso 1 1 calc R . . . .
H30B H -0.190133 0.743025 0.541816 0.019 Uiso 1 1 calc R . . . .
C31 C -0.0869(2) 0.73657(12) 0.68802(13) 0.0165(3) Uani 1 1 d . . . . .
H31 H -0.041791 0.768876 0.743649 0.020 Uiso 1 1 calc R . . . .
C32 C -0.0762(2) 0.65598(12) 0.69925(13) 0.0181(4) Uani 1 1 d . . . . .
H32 H -0.112715 0.620293 0.645179 0.022 Uiso 1 1 calc R . . . .
C33 C -0.0062(2) 0.62211(12) 0.79783(14) 0.0179(4) Uani 1 1 d . . . . .
C34 C 0.0478(3) 0.50159(13) 0.89301(15) 0.0255(4) Uani 1 1 d . . . . .
H34A H 0.052689 0.441751 0.884778 0.038 Uiso 1 1 calc GR . . . .
H34B H -0.043372 0.515512 0.943723 0.038 Uiso 1 1 calc GR . . . .
H34C H 0.173011 0.521967 0.915037 0.038 Uiso 1 1 calc GR . . . .


_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 1.447(2) . ?
O1 C2 1.340(2) . ?
O2 C2 1.208(2) . ?
O3 C4 1.472(2) . ?
O3 C5 1.352(2) . ?
O4 C5 1.203(2) . ?
O5 C16 1.205(2) . ?
O6 C16 1.342(2) . ?
O6 C17 1.446(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.478(2) . ?
C3 C4 1.504(3) . ?
C3 C6 1.333(2) . ?
C4 H4 1.0000 . ?
C4 C9 1.537(2) . ?
C5 C7 1.517(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.509(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.576(2) . ?
C8 C9 1.567(2) . ?
C8 C12 1.545(3) . ?
C8 C13 1.542(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.545(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.536(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.538(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.500(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.323(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.484(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O7 C18 1.448(2) . ?
O7 C19 1.345(2) . ?
O8 C19 1.206(2) . ?
O9 C21 1.475(2) . ?
O9 C25 1.353(2) . ?
O10 C25 1.201(2) . ?
O11 C33 1.346(2) . ?
O11 C34 1.450(2) . ?
O12 C33 1.203(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.472(2) . ?
C20 C21 1.508(3) . ?
C20 C26 1.333(2) . ?
C21 H21 1.0000 . ?
C21 C22 1.534(2) . ?
C22 H22 1.0000 . ?
C22 C23 1.571(2) . ?
C22 C27 1.544(3) . ?
C23 C24 1.578(2) . ?
C23 C29 1.544(2) . ?
C23 C30 1.543(2) . ?
C24 H24 1.0000 . ?
C24 C25 1.517(3) . ?
C24 C26 1.508(2) . ?
C26 H26 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.534(2) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.533(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.498(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.321(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.485(2) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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
C2 O1 C1 115.12(14) . . ?
C5 O3 C4 112.93(13) . . ?
C16 O6 C17 115.01(15) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 111.99(15) . . ?
O2 C2 O1 123.92(17) . . ?
O2 C2 C3 124.09(17) . . ?
C2 C3 C4 120.98(15) . . ?
C6 C3 C2 125.96(17) . . ?
C6 C3 C4 113.05(16) . . ?
O3 C4 C3 107.81(14) . . ?
O3 C4 H4 110.7 . . ?
O3 C4 C9 107.19(14) . . ?
C3 C4 H4 110.7 . . ?
C3 C4 C9 109.54(14) . . ?
C9 C4 H4 110.7 . . ?
O3 C5 C7 113.04(15) . . ?
O4 C5 O3 120.36(17) . . ?
O4 C5 C7 126.59(17) . . ?
C3 C6 H6 123.4 . . ?
C3 C6 C7 113.29(17) . . ?
C7 C6 H6 123.4 . . ?
C5 C7 H7 111.9 . . ?
C5 C7 C8 107.09(14) . . ?
C6 C7 C5 105.91(14) . . ?
C6 C7 H7 111.9 . . ?
C6 C7 C8 107.67(13) . . ?
C8 C7 H7 111.9 . . ?
C9 C8 C7 107.54(13) . . ?
C12 C8 C7 111.19(14) . . ?
C12 C8 C9 105.38(14) . . ?
C13 C8 C7 109.39(14) . . ?
C13 C8 C9 111.82(14) . . ?
C13 C8 C12 111.42(14) . . ?
C4 C9 C8 108.03(14) . . ?
C4 C9 H9 109.8 . . ?
C4 C9 C10 112.95(15) . . ?
C8 C9 H9 109.8 . . ?
C10 C9 C8 106.34(14) . . ?
C10 C9 H9 109.8 . . ?
C9 C10 H10A 110.5 . . ?
C9 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
C11 C10 C9 106.07(15) . . ?
C11 C10 H10A 110.5 . . ?
C11 C10 H10B 110.5 . . ?
C10 C11 H11A 111.1 . . ?
C10 C11 H11B 111.1 . . ?
C10 C11 C12 103.33(15) . . ?
H11A C11 H11B 109.1 . . ?
C12 C11 H11A 111.1 . . ?
C12 C11 H11B 111.1 . . ?
C8 C12 H12A 110.4 . . ?
C8 C12 H12B 110.4 . . ?
C11 C12 C8 106.54(14) . . ?
C11 C12 H12A 110.4 . . ?
C11 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C8 C13 H13A 109.2 . . ?
C8 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 C8 112.27(14) . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C13 C14 H14 117.4 . . ?
C15 C14 C13 125.20(17) . . ?
C15 C14 H14 117.4 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.10(18) . . ?
C16 C15 H15 119.4 . . ?
O5 C16 O6 123.75(17) . . ?
O5 C16 C15 125.81(18) . . ?
O6 C16 C15 110.44(16) . . ?
O6 C17 H17A 109.5 . . ?
O6 C17 H17B 109.5 . . ?
O6 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 O7 C18 115.42(15) . . ?
C25 O9 C21 113.15(13) . . ?
C33 O11 C34 114.68(15) . . ?
O7 C18 H18A 109.5 . . ?
O7 C18 H18B 109.5 . . ?
O7 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O7 C19 C20 112.02(15) . . ?
O8 C19 O7 123.63(17) . . ?
O8 C19 C20 124.35(17) . . ?
C19 C20 C21 119.88(15) . . ?
C26 C20 C19 127.37(17) . . ?
C26 C20 C21 112.74(15) . . ?
O9 C21 C20 107.97(14) . . ?
O9 C21 H21 110.7 . . ?
O9 C21 C22 108.12(13) . . ?
C20 C21 H21 110.7 . . ?
C20 C21 C22 108.63(14) . . ?
C22 C21 H21 110.7 . . ?
C21 C22 H22 109.5 . . ?
C21 C22 C23 107.73(14) . . ?
C21 C22 C27 114.24(15) . . ?
C23 C22 H22 109.5 . . ?
C27 C22 H22 109.5 . . ?
C27 C22 C23 106.26(14) . . ?
C22 C23 C24 107.83(13) . . ?
C29 C23 C22 104.54(14) . . ?
C29 C23 C24 113.42(13) . . ?
C30 C23 C22 110.51(14) . . ?
C30 C23 C24 108.79(14) . . ?
C30 C23 C29 111.63(14) . . ?
C23 C24 H24 112.0 . . ?
C25 C24 C23 105.55(14) . . ?
C25 C24 H24 112.0 . . ?
C26 C24 C23 108.26(13) . . ?
C26 C24 H24 112.0 . . ?
C26 C24 C25 106.58(14) . . ?
O9 C25 C24 112.84(14) . . ?
O10 C25 O9 120.77(17) . . ?
O10 C25 C24 126.32(17) . . ?
C20 C26 C24 113.69(16) . . ?
C20 C26 H26 123.2 . . ?
C24 C26 H26 123.2 . . ?
C22 C27 H27A 110.9 . . ?
C22 C27 H27B 110.9 . . ?
H27A C27 H27B 108.9 . . ?
C28 C27 C22 104.19(14) . . ?
C28 C27 H27A 110.9 . . ?
C28 C27 H27B 110.9 . . ?
C27 C28 H28A 111.3 . . ?
C27 C28 H28B 111.3 . . ?
H28A C28 H28B 109.2 . . ?
C29 C28 C27 102.57(14) . . ?
C29 C28 H28A 111.3 . . ?
C29 C28 H28B 111.3 . . ?
C23 C29 H29A 110.9 . . ?
C23 C29 H29B 110.9 . . ?
C28 C29 C23 104.38(14) . . ?
C28 C29 H29A 110.9 . . ?
C28 C29 H29B 110.9 . . ?
H29A C29 H29B 108.9 . . ?
C23 C30 H30A 109.0 . . ?
C23 C30 H30B 109.0 . . ?
H30A C30 H30B 107.8 . . ?
C31 C30 C23 113.07(14) . . ?
C31 C30 H30A 109.0 . . ?
C31 C30 H30B 109.0 . . ?
C30 C31 H31 116.4 . . ?
C32 C31 C30 127.11(17) . . ?
C32 C31 H31 116.4 . . ?
C31 C32 H32 120.6 . . ?
C31 C32 C33 118.86(17) . . ?
C33 C32 H32 120.6 . . ?
O11 C33 C32 111.32(16) . . ?
O12 C33 O11 123.07(18) . . ?
O12 C33 C32 125.60(18) . . ?
O11 C34 H34A 109.5 . . ?
O11 C34 H34B 109.5 . . ?
O11 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

_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_0761_cole
_database_code_depnum_ccdc_archive 'CCDC 1965041'
loop_
_audit_author_name
_audit_author_address
'Alexander Filatov'
;the University of Chicago
United States of America
;
_audit_update_record             
;
2019-11-11 deposited with the CCDC.	2020-01-22 downloaded from the CCDC.
;
_audit_creation_date             2019-04-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H29 N O8'
_chemical_formula_sum            'C27 H29 N O8'
_chemical_formula_weight         495.51
_chemical_absolute_configuration .
_chemical_melting_point          ?
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'

_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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
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                   26.9187(10)
_cell_length_b                   7.6682(3)
_cell_length_c                   12.9814(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.271(3)
_cell_angle_gamma                90
_cell_volume                     2544.50(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9209
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.72
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1392 before and 0.0446 after correction. 
The Ratio of minimum to maximum transmission is 0.9233. 
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            44278
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.803
_diffrn_reflns_theta_min         2.631
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  D8Venture
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus X-ray tube'
_diffrn_source_type              'INCOATEC ImuS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.861
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                6933
_reflns_number_total             7883
_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       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material  
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'XL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'XT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 2882 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         7883
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.040
_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)+(0.0490P)²+0.4987P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0876
_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 Ternary CH refined with riding coordinates:
 C16(H16), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C20(H20), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C19(H19A,H19B,H19C),
 C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.78198(5) 0.13583(17) 0.71633(10) 0.0204(3) Uani 1 1 d . . . . .
O2 O 0.69796(5) 0.09769(17) 0.60971(10) 0.0212(3) Uani 1 1 d . . . . .
O3 O 0.61235(5) 0.79366(16) 0.57046(9) 0.0166(2) Uani 1 1 d . . . . .
O4 O 0.59292(5) 0.53428(17) 0.49279(9) 0.0193(2) Uani 1 1 d . . . . .
O5 O 0.54368(5) 0.06202(17) 0.88079(10) 0.0230(3) Uani 1 1 d . . . . .
O6 O 0.46533(5) 0.1797(2) 0.86663(10) 0.0264(3) Uani 1 1 d . . . . .
O7 O 0.52933(5) 1.18443(17) 0.63499(10) 0.0222(3) Uani 1 1 d . . . . .
O8 O 0.46186(5) 0.99920(16) 0.61121(10) 0.0196(3) Uani 1 1 d . . . . .
N1 N 0.71968(5) 0.31128(19) 0.73757(11) 0.0150(3) Uani 1 1 d . . . . .
C1 C 0.86195(8) 0.0045(4) 0.73140(19) 0.0402(6) Uani 1 1 d . . . . .
H1A H 0.874455 0.119538 0.717789 0.060 Uiso 1 1 calc GR . . . .
H1B H 0.881338 -0.086288 0.707046 0.060 Uiso 1 1 calc GR . . . .
H1C H 0.867425 -0.009225 0.809244 0.060 Uiso 1 1 calc GR . . . .
C2 C 0.79353(8) 0.0164(3) 0.54894(16) 0.0312(4) Uani 1 1 d . . . . .
H2A H 0.756080 0.002202 0.510758 0.047 Uiso 1 1 calc GR . . . .
H2B H 0.813375 -0.069016 0.521557 0.047 Uiso 1 1 calc GR . . . .
H2C H 0.804421 0.134486 0.536627 0.047 Uiso 1 1 calc GR . . . .
C3 C 0.78145(10) -0.1817(3) 0.69430(19) 0.0373(5) Uani 1 1 d . . . . .
H3A H 0.786677 -0.189235 0.772352 0.056 Uiso 1 1 calc GR . . . .
H3B H 0.799172 -0.279661 0.672128 0.056 Uiso 1 1 calc GR . . . .
H3C H 0.743944 -0.186360 0.654491 0.056 Uiso 1 1 calc GR . . . .
C4 C 0.80390(7) -0.0120(3) 0.66949(15) 0.0245(4) Uani 1 1 d . . . . .
C5 C 0.73133(6) 0.1703(2) 0.68056(13) 0.0164(3) Uani 1 1 d . . . . .
C6 C 0.75188(6) 0.4117(2) 0.82303(13) 0.0141(3) Uani 1 1 d . . . . .
C7 C 0.80565(6) 0.4053(2) 0.87622(13) 0.0164(3) Uani 1 1 d . . . . .
H7 H 0.827386 0.322860 0.856434 0.020 Uiso 1 1 calc R . . . .
C8 C 0.82607(6) 0.5245(2) 0.95927(13) 0.0178(3) Uani 1 1 d . . . . .
H8 H 0.862595 0.524039 0.996527 0.021 Uiso 1 1 calc R . . . .
C9 C 0.79432(6) 0.6449(2) 0.98937(13) 0.0193(3) Uani 1 1 d . . . . .
H9 H 0.809423 0.722951 1.047618 0.023 Uiso 1 1 calc R . . . .
C10 C 0.74095(6) 0.6523(2) 0.93537(13) 0.0175(3) Uani 1 1 d . . . . .
H10 H 0.719495 0.734713 0.956035 0.021 Uiso 1 1 calc R . . . .
C11 C 0.71936(6) 0.5361(2) 0.85005(12) 0.0139(3) Uani 1 1 d . . . . .
C12 C 0.66666(6) 0.5121(2) 0.77593(12) 0.0131(3) Uani 1 1 d . . . . .
C13 C 0.66875(6) 0.3760(2) 0.71123(13) 0.0149(3) Uani 1 1 d . . . . .
H13 H 0.639609 0.330755 0.655572 0.018 Uiso 1 1 calc R . . . .
C14 C 0.62006(6) 0.6268(2) 0.76958(12) 0.0124(3) Uani 1 1 d . . . . .
C15 C 0.63497(6) 0.8229(2) 0.76483(13) 0.0152(3) Uani 1 1 d . . . . .
H15A H 0.628191 0.888042 0.824904 0.018 Uiso 1 1 calc R . . . .
H15B H 0.672632 0.833362 0.772611 0.018 Uiso 1 1 calc R . . . .
C16 C 0.60219(6) 0.8983(2) 0.65622(13) 0.0147(3) Uani 1 1 d . . . . .
H16 H 0.611435 1.023312 0.649949 0.018 Uiso 1 1 calc R . . . .
C17 C 0.54519(6) 0.8806(2) 0.64600(12) 0.0134(3) Uani 1 1 d . . . . .
C18 C 0.51245(6) 1.0381(2) 0.63135(12) 0.0149(3) Uani 1 1 d . . . . .
C19 C 0.42657(7) 1.1467(3) 0.58724(15) 0.0256(4) Uani 1 1 d . . . . .
H19A H 0.432350 1.215342 0.528326 0.038 Uiso 1 1 calc GR . . . .
H19B H 0.433116 1.219837 0.652065 0.038 Uiso 1 1 calc GR . . . .
H19C H 0.390343 1.104977 0.565091 0.038 Uiso 1 1 calc GR . . . .
C20 C 0.53041(6) 0.7155(2) 0.65056(12) 0.0128(3) Uani 1 1 d . . . . .
H20 H 0.495923 0.682330 0.647103 0.015 Uiso 1 1 calc R . . . .
C21 C 0.57432(6) 0.5870(2) 0.66179(12) 0.0126(3) Uani 1 1 d . . . . .
H21 H 0.561963 0.463588 0.659109 0.015 Uiso 1 1 calc R . . . .
C22 C 0.59394(6) 0.6298(2) 0.56696(13) 0.0145(3) Uani 1 1 d . . . . .
C23 C 0.60027(6) 0.5939(2) 0.86826(13) 0.0162(3) Uani 1 1 d . . . . .
H23A H 0.629353 0.615130 0.935935 0.019 Uiso 1 1 calc R . . . .
H23B H 0.572118 0.678394 0.865855 0.019 Uiso 1 1 calc R . . . .
C24 C 0.57992(6) 0.4133(2) 0.87113(13) 0.0169(3) Uani 1 1 d . . . . .
H24 H 0.602407 0.319555 0.867658 0.020 Uiso 1 1 calc R . . . .
C25 C 0.53330(7) 0.3725(3) 0.87808(14) 0.0201(3) Uani 1 1 d . . . . .
H25 H 0.510231 0.462779 0.884293 0.024 Uiso 1 1 calc R . . . .
C26 C 0.51661(7) 0.1889(3) 0.87633(13) 0.0197(4) Uani 1 1 d . . . . .
C27 C 0.44342(8) 0.0064(3) 0.85653(17) 0.0321(5) Uani 1 1 d . . . . .
H27A H 0.453436 -0.058222 0.800965 0.048 Uiso 1 1 calc GR . . . .
H27B H 0.405198 0.014057 0.835580 0.048 Uiso 1 1 calc GR . . . .
H27C H 0.456739 -0.054415 0.926199 0.048 Uiso 1 1 calc GR . . . .


_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 C4 1.492(2) . ?
O1 C5 1.322(2) . ?
O2 C5 1.202(2) . ?
O3 C16 1.4659(19) . ?
O3 C22 1.346(2) . ?
O4 C22 1.203(2) . ?
O5 C26 1.206(2) . ?
O6 C26 1.348(2) . ?
O6 C27 1.444(3) . ?
O7 C18 1.206(2) . ?
O8 C18 1.337(2) . ?
O8 C19 1.447(2) . ?
N1 C5 1.400(2) . ?
N1 C6 1.405(2) . ?
N1 C13 1.396(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C4 1.522(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 C4 1.517(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C3 C4 1.512(3) . ?
C6 C7 1.396(2) . ?
C6 C11 1.411(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.394(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.398(2) . ?
C11 C12 1.455(2) . ?
C12 C13 1.352(2) . ?
C12 C14 1.513(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.563(2) . ?
C14 C21 1.577(2) . ?
C14 C23 1.554(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.523(2) . ?
C16 H16 1.0000 . ?
C16 C17 1.504(2) . ?
C17 C18 1.472(2) . ?
C17 C20 1.333(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20 0.9500 . ?
C20 C21 1.511(2) . ?
C21 H21 1.0000 . ?
C21 C22 1.520(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.494(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.324(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.476(3) . ?
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
C5 O1 C4 120.31(13) . . ?
C22 O3 C16 112.47(12) . . ?
C26 O6 C27 115.72(16) . . ?
C18 O8 C19 115.29(14) . . ?
C5 N1 C6 130.99(13) . . ?
C13 N1 C5 120.71(13) . . ?
C13 N1 C6 108.29(13) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
O1 C4 C1 101.16(15) . . ?
O1 C4 C2 110.05(16) . . ?
O1 C4 C3 109.37(14) . . ?
C2 C4 C1 111.06(17) . . ?
C3 C4 C1 111.82(19) . . ?
C3 C4 C2 112.76(18) . . ?
O1 C5 N1 110.25(14) . . ?
O2 C5 O1 128.11(16) . . ?
O2 C5 N1 121.63(15) . . ?
N1 C6 C11 106.85(13) . . ?
C7 C6 N1 131.22(15) . . ?
C7 C6 C11 121.92(15) . . ?
C6 C7 H7 121.4 . . ?
C8 C7 C6 117.23(15) . . ?
C8 C7 H7 121.4 . . ?
C7 C8 H8 119.2 . . ?
C7 C8 C9 121.68(14) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.90(15) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.79(15) . . ?
C11 C10 H10 120.6 . . ?
C6 C11 C12 107.59(14) . . ?
C10 C11 C6 119.43(14) . . ?
C10 C11 C12 132.98(15) . . ?
C11 C12 C14 125.62(14) . . ?
C13 C12 C11 106.67(14) . . ?
C13 C12 C14 127.60(14) . . ?
N1 C13 H13 124.7 . . ?
C12 C13 N1 110.57(14) . . ?
C12 C13 H13 124.7 . . ?
C12 C14 C15 110.03(12) . . ?
C12 C14 C21 109.84(12) . . ?
C12 C14 C23 110.70(13) . . ?
C15 C14 C21 106.85(12) . . ?
C23 C14 C15 110.31(13) . . ?
C23 C14 C21 109.02(12) . . ?
C14 C15 H15A 110.0 . . ?
C14 C15 H15B 110.0 . . ?
H15A C15 H15B 108.3 . . ?
C16 C15 C14 108.68(13) . . ?
C16 C15 H15A 110.0 . . ?
C16 C15 H15B 110.0 . . ?
O3 C16 C15 107.66(13) . . ?
O3 C16 H16 110.6 . . ?
O3 C16 C17 108.14(12) . . ?
C15 C16 H16 110.6 . . ?
C17 C16 C15 109.04(13) . . ?
C17 C16 H16 110.6 . . ?
C18 C17 C16 119.34(14) . . ?
C20 C17 C16 113.09(14) . . ?
C20 C17 C18 127.56(15) . . ?
O7 C18 O8 124.28(15) . . ?
O7 C18 C17 123.75(15) . . ?
O8 C18 C17 111.96(14) . . ?
O8 C19 H19A 109.5 . . ?
O8 C19 H19B 109.5 . . ?
O8 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20 123.6 . . ?
C17 C20 C21 112.85(14) . . ?
C21 C20 H20 123.6 . . ?
C14 C21 H21 111.9 . . ?
C20 C21 C14 109.22(12) . . ?
C20 C21 H21 111.9 . . ?
C20 C21 C22 103.93(12) . . ?
C22 C21 C14 107.69(12) . . ?
C22 C21 H21 111.9 . . ?
O3 C22 C21 113.09(13) . . ?
O4 C22 O3 120.74(15) . . ?
O4 C22 C21 126.15(15) . . ?
C14 C23 H23A 108.9 . . ?
C14 C23 H23B 108.9 . . ?
H23A C23 H23B 107.8 . . ?
C24 C23 C14 113.20(13) . . ?
C24 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C23 C24 H24 117.1 . . ?
C25 C24 C23 125.71(16) . . ?
C25 C24 H24 117.1 . . ?
C24 C25 H25 119.5 . . ?
C24 C25 C26 121.00(17) . . ?
C26 C25 H25 119.5 . . ?
O5 C26 O6 123.21(17) . . ?
O5 C26 C25 126.33(16) . . ?
O6 C26 C25 110.44(16) . . ?
O6 C27 H27A 109.5 . . ?
O6 C27 H27B 109.5 . . ?
O6 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
