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

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

data_suyu0111
_database_code_depnum_ccdc_archive 'CCDC 926785'
_audit_update_record             
;
2013-02-27 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;
#TrackingRef 'suyu0111.cif'

_audit_creation_date             2013-02-27
_audit_creation_method           
;
Olex2 1.2
(compiled Dec 5 2012 16:20:19, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C19 H17 Br O4'
_chemical_formula_sum            'C19 H16 Br O4'
_chemical_formula_weight         388.23
_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 0.0033 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   5.8959(3)
_cell_length_b                   11.7317(6)
_cell_length_c                   12.7300(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.833(6)
_cell_angle_gamma                90.00
_cell_volume                     874.27(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    848
_cell_measurement_temperature    293.66(10)
_cell_measurement_theta_max      28.3836
_cell_measurement_theta_min      3.2170
_exptl_absorpt_coefficient_mu    2.370
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             394
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
?
;
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3487
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.22
_diffrn_ambient_temperature      293.66(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.9788
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega -10.00 17.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -19.3492 -99.0000 -30.0000 27

#__ type_ start__ end____ width___ exp.time_
2 omega -35.00 52.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 22.7867 -77.0000 -180.0000 87

#__ type_ start__ end____ width___ exp.time_
3 omega -29.00 83.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 22.7867 19.0000 30.0000 112
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0050908000
_diffrn_orient_matrix_UB_12      -0.0145926000
_diffrn_orient_matrix_UB_13      -0.0543085000
_diffrn_orient_matrix_UB_21      -0.0308134000
_diffrn_orient_matrix_UB_22      0.0568975000
_diffrn_orient_matrix_UB_23      -0.0141303000
_diffrn_orient_matrix_UB_31      0.1170714000
_diffrn_orient_matrix_UB_32      0.0143095000
_diffrn_orient_matrix_UB_33      0.0008627000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1727
_reflns_number_total             2479
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.021(16)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2479
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0522
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0519P)²+0.1199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1240
_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_olex2_refinement_description    
;
1. Fixed Uiso
At 1.2 times of:
H9 of C9, H10 of C10, H11 of C11, {H12A,H12B} of C12, H15 of C15, H16 of
C16, H18 of C18, H19 of C19, H8 of C8, H1 of C1, H3A of C3, H4 of C4, {H5A,
H5B} of C5, H7 of C7
At 1.5 times of:
H3 of O3
2. Uiso/Uaniso restraints and constraints
Uanis(C11) ~ Ueq, Uanis(C10) ~ Ueq, Uanis(C9) ~ Ueq, Uanis(C8) ~ Ueq, Uanis(C7) ~ Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
C1(H1), C3(H3A), C4(H4)
3.b Secondary CH2 refined with riding coordinates:
C5(H5A,H5B), C12(H12A,H12B)
3.c Aromatic/amide H refined with riding coordinates:
C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16), C18(H18),
C19(H19)
3.d Idealised tetrahedral OH refined as rotating group:
O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.83531(15) -0.19700(7) -0.31763(7) 0.0866(3) Uani 1 1 d . . .
O1 O -1.5081(8) -0.7930(4) 0.0567(3) 0.0603(13) Uani 1 1 d . . .
O2 O -1.5357(7) -0.9496(4) -0.0419(3) 0.0487(11) Uani 1 1 d . . .
O3 O -1.2709(8) -1.0849(4) -0.0805(4) 0.0572(12) Uani 1 1 d . . .
H3 H -1.3458 -1.1398 -0.0644 0.086 Uiso 1 1 calc R . .
O4 O -0.8597(8) -0.7465(4) -0.1528(4) 0.0710(14) Uani 1 1 d . . .
C1 C -1.2336(10) -0.8256(5) -0.0694(4) 0.0373(13) Uani 1 1 d . . .
H1 H -1.0964 -0.8534 -0.0260 0.045 Uiso 1 1 calc R . .
C2 C -1.4358(11) -0.8498(6) -0.0110(4) 0.0433(15) Uani 1 1 d . . .
C3 C -1.4161(10) -1.0013(5) -0.1241(4) 0.0405(14) Uani 1 1 d . . .
H3A H -1.5257 -1.0329 -0.1805 0.049 Uiso 1 1 calc R . .
C4 C -1.2798(10) -0.9047(5) -0.1667(4) 0.0346(13) Uani 1 1 d . . .
H4 H -1.1348 -0.9344 -0.1859 0.042 Uiso 1 1 calc R . .
C5 C -1.4120(10) -0.8457(6) -0.2630(4) 0.0454(15) Uani 1 1 d . . .
H5A H -1.5477 -0.8110 -0.2407 0.054 Uiso 1 1 calc R . .
H5B H -1.3176 -0.7848 -0.2856 0.054 Uiso 1 1 calc R . .
C6 C -1.4845(10) -0.9215(6) -0.3574(4) 0.0460(16) Uani 1 1 d . . .
C7 C -1.6986(14) -0.9069(8) -0.4128(6) 0.075(2) Uani 1 1 d U . .
H7 H -1.7991 -0.8527 -0.3918 0.090 Uiso 1 1 calc R . .
C8 C -1.7624(16) -0.9777(10) -0.5039(6) 0.089(3) Uani 1 1 d U . .
H8 H -1.9050 -0.9684 -0.5429 0.106 Uiso 1 1 calc R . .
C9 C -1.6220(19) -1.0550(11) -0.5326(7) 0.091(3) Uani 1 1 d U . .
H9 H -1.6673 -1.1005 -0.5912 0.109 Uiso 1 1 calc R . .
C10 C -1.4159(19) -1.0698(10) -0.4796(7) 0.096(3) Uani 1 1 d U . .
H10 H -1.3183 -1.1246 -0.5020 0.115 Uiso 1 1 calc R . .
C11 C -1.3449(13) -1.0037(8) -0.3905(5) 0.072(2) Uani 1 1 d U . .
H11 H -1.2013 -1.0158 -0.3533 0.086 Uiso 1 1 calc R . .
C12 C -1.2047(9) -0.6978(7) -0.0862(4) 0.0408(12) Uani 1 1 d . . .
H12A H -1.3407 -0.6680 -0.1275 0.049 Uiso 1 1 calc R . .
H12B H -1.1874 -0.6596 -0.0182 0.049 Uiso 1 1 calc R . .
C13 C -0.9994(10) -0.6729(5) -0.1427(4) 0.0402(14) Uani 1 1 d . . .
C14 C -0.9685(10) -0.5557(5) -0.1829(4) 0.0371(14) Uani 1 1 d . . .
C15 C -1.1127(10) -0.4660(5) -0.1671(4) 0.0398(14) Uani 1 1 d . . .
H15 H -1.2367 -0.4782 -0.1297 0.048 Uiso 1 1 calc R . .
C16 C -1.0754(12) -0.3581(6) -0.2061(5) 0.0490(16) Uani 1 1 d . . .
H16 H -1.1723 -0.2979 -0.1949 0.059 Uiso 1 1 calc R . .
C17 C -0.8909(11) -0.3421(6) -0.2621(5) 0.0453(15) Uani 1 1 d . . .
C18 C -0.7469(11) -0.4298(7) -0.2790(5) 0.0549(18) Uani 1 1 d . . .
H18 H -0.6232 -0.4172 -0.3165 0.066 Uiso 1 1 calc R . .
C19 C -0.7853(10) -0.5358(6) -0.2406(5) 0.0485(16) Uani 1 1 d . . .
H19 H -0.6881 -0.5955 -0.2529 0.058 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 C17 1.887(6) . ?
O1 C2 1.206(7) . ?
O2 C2 1.348(7) . ?
O2 C3 1.461(7) . ?
O3 H3 0.8200 . ?
O3 C3 1.375(7) . ?
O4 C13 1.211(7) . ?
C1 H1 0.9800 . ?
C1 C2 1.505(8) . ?
C1 C4 1.546(8) . ?
C1 C12 1.527(9) . ?
C3 H3A 0.9800 . ?
C3 C4 1.526(8) . ?
C4 H4 0.9800 . ?
C4 C5 1.537(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.515(9) . ?
C6 C7 1.382(9) . ?
C6 C11 1.367(10) . ?
C7 H7 0.9300 . ?
C7 C8 1.440(12) . ?
C8 H8 0.9300 . ?
C8 C9 1.309(14) . ?
C9 H9 0.9300 . ?
C9 C10 1.329(12) . ?
C10 H10 0.9300 . ?
C10 C11 1.396(11) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.508(8) . ?
C13 C14 1.486(8) . ?
C14 C15 1.382(8) . ?
C14 C19 1.396(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(9) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(8) . ?
C17 C18 1.367(10) . ?
C18 H18 0.9300 . ?
C18 C19 1.365(10) . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 C3 109.8(4) . . ?
C3 O3 H3 109.5 . . ?
C2 C1 H1 107.9 . . ?
C2 C1 C4 102.0(5) . . ?
C2 C1 C12 111.3(5) . . ?
C4 C1 H1 107.9 . . ?
C12 C1 H1 107.9 . . ?
C12 C1 C4 119.3(4) . . ?
O1 C2 O2 120.6(5) . . ?
O1 C2 C1 128.1(6) . . ?
O2 C2 C1 111.3(5) . . ?
O2 C3 H3A 110.5 . . ?
O2 C3 C4 105.4(5) . . ?
O3 C3 O2 109.8(5) . . ?
O3 C3 H3A 110.5 . . ?
O3 C3 C4 110.1(5) . . ?
C4 C3 H3A 110.5 . . ?
C1 C4 H4 109.7 . . ?
C3 C4 C1 102.2(4) . . ?
C3 C4 H4 109.7 . . ?
C3 C4 C5 112.3(5) . . ?
C5 C4 C1 113.1(5) . . ?
C5 C4 H4 109.7 . . ?
C4 C5 H5A 108.3 . . ?
C4 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
C6 C5 C4 115.9(5) . . ?
C6 C5 H5A 108.3 . . ?
C6 C5 H5B 108.3 . . ?
C7 C6 C5 119.1(6) . . ?
C11 C6 C5 122.3(5) . . ?
C11 C6 C7 118.5(6) . . ?
C6 C7 H7 120.8 . . ?
C6 C7 C8 118.4(8) . . ?
C8 C7 H7 120.8 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.7(9) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.3(9) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.5(9) . . ?
C11 C10 H10 119.7 . . ?
C6 C11 C10 120.6(8) . . ?
C6 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C1 C12 H12A 109.3 . . ?
C1 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 C1 111.5(6) . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
O4 C13 C12 120.5(6) . . ?
O4 C13 C14 120.7(5) . . ?
C14 C13 C12 118.8(5) . . ?
C15 C14 C13 123.5(5) . . ?
C15 C14 C19 118.5(6) . . ?
C19 C14 C13 118.0(6) . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.1(5) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 120.8 . . ?
C17 C16 C15 118.4(6) . . ?
C17 C16 H16 120.8 . . ?
C16 C17 Br1 119.8(5) . . ?
C18 C17 Br1 118.8(5) . . ?
C18 C17 C16 121.4(6) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(6) . . ?
C19 C18 H18 120.1 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.8(6) . . ?
C18 C19 H19 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C17 C18 C19 -179.3(5) . . . . ?
O2 C3 C4 C1 28.9(6) . . . . ?
O2 C3 C4 C5 -92.6(5) . . . . ?
O3 C3 C4 C1 -89.4(5) . . . . ?
O3 C3 C4 C5 149.1(5) . . . . ?
O4 C13 C14 C15 -175.1(6) . . . . ?
O4 C13 C14 C19 5.5(8) . . . . ?
C1 C4 C5 C6 -173.9(5) . . . . ?
C1 C12 C13 O4 -12.6(7) . . . . ?
C1 C12 C13 C14 169.1(5) . . . . ?
C2 O2 C3 O3 100.3(5) . . . . ?
C2 O2 C3 C4 -18.3(6) . . . . ?
C2 C1 C4 C3 -28.3(6) . . . . ?
C2 C1 C4 C5 92.6(5) . . . . ?
C2 C1 C12 C13 178.8(4) . . . . ?
C3 O2 C2 O1 -179.9(5) . . . . ?
C3 O2 C2 C1 -0.9(7) . . . . ?
C3 C4 C5 C6 -58.9(7) . . . . ?
C4 C1 C2 O1 -161.9(6) . . . . ?
C4 C1 C2 O2 19.2(6) . . . . ?
C4 C1 C12 C13 -62.9(7) . . . . ?
C4 C5 C6 C7 139.4(6) . . . . ?
C4 C5 C6 C11 -41.0(9) . . . . ?
C5 C6 C7 C8 178.4(7) . . . . ?
C5 C6 C11 C10 -178.3(7) . . . . ?
C6 C7 C8 C9 0.9(13) . . . . ?
C7 C6 C11 C10 1.3(11) . . . . ?
C7 C8 C9 C10 -0.8(15) . . . . ?
C8 C9 C10 C11 0.9(15) . . . . ?
C9 C10 C11 C6 -1.2(14) . . . . ?
C11 C6 C7 C8 -1.2(11) . . . . ?
C12 C1 C2 O1 -33.6(8) . . . . ?
C12 C1 C2 O2 147.5(5) . . . . ?
C12 C1 C4 C3 -151.4(5) . . . . ?
C12 C1 C4 C5 -30.4(7) . . . . ?
C12 C13 C14 C15 3.2(8) . . . . ?
C12 C13 C14 C19 -176.2(5) . . . . ?
C13 C14 C15 C16 179.7(5) . . . . ?
C13 C14 C19 C18 -179.5(6) . . . . ?
C14 C15 C16 C17 0.4(9) . . . . ?
C15 C14 C19 C18 1.1(9) . . . . ?
C15 C16 C17 Br1 179.5(5) . . . . ?
C15 C16 C17 C18 -0.2(10) . . . . ?
C16 C17 C18 C19 0.4(10) . . . . ?
C17 C18 C19 C14 -0.8(10) . . . . ?
C19 C14 C15 C16 -0.9(9) . . . . ?



####################################################################### 
# 
# 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_lingjb1118
_database_code_depnum_ccdc_archive 'CCDC 1035631'
_audit_update_record             
;
2014-11-23 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;
_audit_creation_date             2014-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4866)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H18 O4'
_chemical_formula_sum            'C19 H18 O4'
_chemical_formula_weight         310.33
_chemical_absolute_configuration unk
_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'

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

_cell_length_a                   5.6167(3)
_cell_length_b                   25.0791(11)
_cell_length_c                   11.3191(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.779(5)
_cell_angle_gamma                90.00
_cell_volume                     1594.28(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1149
_cell_measurement_temperature    294.68(10)
_cell_measurement_theta_max      22.2370
_cell_measurement_theta_min      3.9640
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6897
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.60
_diffrn_ambient_temperature      294.68(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -8.00   19.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3571  -99.0000 -120.0000 18

#__ type_ start__ end____ width___ exp.time_
  2 omega    2.00   92.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   38.0000  -90.0000 60

#__ type_ start__ end____ width___ exp.time_
  3 omega   31.00   58.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -99.0000 -150.0000 18

#__ type_ start__ end____ width___ exp.time_
  4 omega    2.00   92.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   38.0000    0.0000 60
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0457676000
_diffrn_orient_matrix_UB_12      -0.0005515000
_diffrn_orient_matrix_UB_13      0.0587176000
_diffrn_orient_matrix_UB_21      -0.1177047000
_diffrn_orient_matrix_UB_22      0.0003730000
_diffrn_orient_matrix_UB_23      0.0218686000
_diffrn_orient_matrix_UB_31      -0.0024318000
_diffrn_orient_matrix_UB_32      -0.0282740000
_diffrn_orient_matrix_UB_33      -0.0008520000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3315
_reflns_number_total             5167
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.1(17)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5167
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0616
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0449P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1424
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11), C12(H12), C29(H29), C31(H31), C32(H32)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C14(H14A,H14B), C28(H28A,H28B), C33(H33A,H33B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4A), C5(H5), C6(H6), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C35(H35),
  C36(H36), C37(H37), C38(H38), C39(H39)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O -1.1511(6) -0.13113(15) -0.1060(3) 0.0665(10) Uani 1 d . . .
O2 O -0.4219(6) -0.24187(13) -0.1686(3) 0.0684(10) Uani 1 d . . .
O3 O -0.4592(6) -0.19877(13) -0.3392(3) 0.0597(9) Uani 1 d . . .
O4 O -0.7801(6) -0.19337(14) -0.4679(3) 0.0636(9) Uani 1 d . . .
H4 H -0.7093 -0.2026 -0.5274 0.095 Uiso 1 calc . . GR
C1 C -1.0050(8) -0.11743(17) 0.0884(4) 0.0441(11) Uani 1 d . . .
C2 C -1.2012(9) -0.0871(2) 0.1177(5) 0.0667(15) Uani 1 d . . .
H2 H -1.3192 -0.0801 0.0614 0.080 Uiso 1 calc . . R
C3 C -1.2208(11) -0.0674(3) 0.2308(6) 0.094(2) Uani 1 d . . .
H3 H -1.3532 -0.0471 0.2503 0.113 Uiso 1 calc . . R
C4 C -1.0508(12) -0.0770(2) 0.3139(5) 0.0749(17) Uani 1 d . . .
H4A H -1.0660 -0.0631 0.3896 0.090 Uiso 1 calc . . R
C5 C -0.8567(11) -0.1070(2) 0.2862(5) 0.0738(17) Uani 1 d . . .
H5 H -0.7400 -0.1139 0.3432 0.089 Uiso 1 calc . . R
C6 C -0.8344(9) -0.12715(19) 0.1738(4) 0.0600(14) Uani 1 d . . .
H6 H -0.7018 -0.1476 0.1553 0.072 Uiso 1 calc . . R
C7 C -0.9852(8) -0.13719(18) -0.0357(4) 0.0460(11) Uani 1 d . . .
C8 C -0.7596(8) -0.16520(18) -0.0712(4) 0.0447(11) Uani 1 d . . .
H8A H -0.7397 -0.1969 -0.0231 0.054 Uiso 1 calc . . R
H8B H -0.6252 -0.1419 -0.0551 0.054 Uiso 1 calc . . R
C9 C -0.7577(8) -0.18116(16) -0.2014(4) 0.0395(10) Uani 1 d . . .
H9 H -0.8917 -0.2055 -0.2156 0.047 Uiso 1 calc . . R
C10 C -0.5316(9) -0.21087(18) -0.2293(4) 0.0510(12) Uani 1 d . . .
C11 C -0.6310(9) -0.16369(18) -0.3973(4) 0.0473(11) Uani 1 d . . .
H11 H -0.5491 -0.1365 -0.4439 0.057 Uiso 1 calc . . R
C12 C -0.7681(8) -0.13770(15) -0.2964(4) 0.0398(10) Uani 1 d . . .
H12 H -0.9340 -0.1323 -0.3214 0.048 Uiso 1 calc . . R
C13 C -0.7128(8) -0.04094(16) -0.3499(4) 0.0433(11) Uani 1 d . . .
C14 C -0.6598(9) -0.08396(16) -0.2593(4) 0.0503(12) Uani 1 d . . .
H14A H -0.7237 -0.0734 -0.1837 0.060 Uiso 1 calc . . R
H14B H -0.4887 -0.0878 -0.2499 0.060 Uiso 1 calc . . R
C16 C -0.5576(9) -0.02834(19) -0.4397(5) 0.0592(14) Uani 1 d . . .
H16 H -0.4147 -0.0469 -0.4454 0.071 Uiso 1 calc . . R
C17 C -0.6099(10) 0.0109(2) -0.5207(5) 0.0673(15) Uani 1 d . . .
H17 H -0.5030 0.0186 -0.5804 0.081 Uiso 1 calc . . R
C18 C -0.8199(11) 0.03894(19) -0.5138(5) 0.0654(15) Uani 1 d . . .
H18 H -0.8564 0.0651 -0.5694 0.079 Uiso 1 calc . . R
C19 C -0.9753(10) 0.02806(19) -0.4245(6) 0.0645(15) Uani 1 d . . .
H19 H -1.1161 0.0473 -0.4183 0.077 Uiso 1 calc . . R
C20 C -0.9216(9) -0.01172(18) -0.3435(5) 0.0568(14) Uani 1 d . . .
H20 H -1.0282 -0.0190 -0.2835 0.068 Uiso 1 calc . . R
O5 O 0.2432(6) -0.31779(16) -0.6127(3) 0.0748(11) Uani 1 d . . .
O6 O -0.4775(7) -0.20350(14) -0.6556(3) 0.0781(12) Uani 1 d . . .
O7 O -0.4673(6) -0.24473(13) -0.8295(3) 0.0633(10) Uani 1 d . . .
O8 O -0.1607(6) -0.25237(14) -0.9643(3) 0.0642(10) Uani 1 d . . .
H8 H -0.2384 -0.2399 -1.0195 0.096 Uiso 1 calc . . GR
C21 C 0.1390(8) -0.32848(15) -0.4146(4) 0.0379(10) Uani 1 d . . .
C22 C -0.0057(9) -0.31526(18) -0.3225(4) 0.0525(12) Uani 1 d . . .
H22 H -0.1407 -0.2946 -0.3365 0.063 Uiso 1 calc . . R
C23 C 0.0470(10) -0.3323(2) -0.2089(5) 0.0648(14) Uani 1 d . . .
H23 H -0.0530 -0.3233 -0.1471 0.078 Uiso 1 calc . . R
C24 C 0.2469(10) -0.36249(19) -0.1871(5) 0.0618(14) Uani 1 d . . .
H24 H 0.2842 -0.3730 -0.1103 0.074 Uiso 1 calc . . R
C25 C 0.3921(9) -0.3772(2) -0.2783(5) 0.0617(14) Uani 1 d . . .
H25 H 0.5247 -0.3985 -0.2640 0.074 Uiso 1 calc . . R
C26 C 0.3390(8) -0.35993(18) -0.3912(4) 0.0521(12) Uani 1 d . . .
H26 H 0.4382 -0.3694 -0.4529 0.063 Uiso 1 calc . . R
C27 C 0.0944(8) -0.31015(17) -0.5382(4) 0.0459(11) Uani 1 d . . .
C28 C -0.1359(8) -0.28308(19) -0.5682(4) 0.0476(11) Uani 1 d . . .
H28A H -0.1527 -0.2518 -0.5184 0.057 Uiso 1 calc . . R
H28B H -0.2663 -0.3071 -0.5509 0.057 Uiso 1 calc . . R
C29 C -0.1544(8) -0.26604(16) -0.6977(4) 0.0447(11) Uani 1 d . . .
H29 H -0.0191 -0.2426 -0.7136 0.054 Uiso 1 calc . . R
C30 C -0.3791(9) -0.23445(19) -0.7205(4) 0.0546(13) Uani 1 d . . .
C31 C -0.3089(9) -0.28104(18) -0.8919(4) 0.0495(12) Uani 1 d . . .
H31 H -0.4010 -0.3072 -0.9377 0.059 Uiso 1 calc . . R
C32 C -0.1626(8) -0.30859(16) -0.7950(4) 0.0417(10) Uani 1 d . . .
H32 H -0.0013 -0.3154 -0.8232 0.050 Uiso 1 calc . . R
C33 C -0.2767(9) -0.36077(16) -0.7567(4) 0.0522(13) Uani 1 d . . .
H33A H -0.1809 -0.3759 -0.6931 0.063 Uiso 1 calc . . R
H33B H -0.4325 -0.3529 -0.7252 0.063 Uiso 1 calc . . R
C34 C -0.3057(9) -0.40253(17) -0.8526(4) 0.0477(11) Uani 1 d . . .
C35 C -0.1402(10) -0.4112(2) -0.9367(5) 0.0779(18) Uani 1 d . . .
H35 H -0.0050 -0.3898 -0.9375 0.093 Uiso 1 calc . . R
C36 C -0.1654(12) -0.4509(2) -1.0216(6) 0.090(2) Uani 1 d . . .
H36 H -0.0497 -0.4556 -1.0787 0.108 Uiso 1 calc . . R
C37 C -0.3624(11) -0.4829(2) -1.0203(6) 0.0765(17) Uani 1 d . . .
H37 H -0.3809 -0.5101 -1.0754 0.092 Uiso 1 calc . . R
C38 C -0.5293(12) -0.4743(3) -0.9381(6) 0.091(2) Uani 1 d . . .
H38 H -0.6648 -0.4957 -0.9379 0.109 Uiso 1 calc . . R
C39 C -0.5041(10) -0.4347(2) -0.8540(6) 0.0737(17) Uani 1 d . . .
H39 H -0.6219 -0.4297 -0.7982 0.088 Uiso 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
O1 C7 1.227(5) . ?
O2 C10 1.202(5) . ?
O3 C10 1.349(5) . ?
O3 C11 1.456(5) . ?
O4 H4 0.8200 . ?
O4 C11 1.370(5) . ?
C1 C2 1.383(6) . ?
C1 C6 1.374(6) . ?
C1 C7 1.495(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.352(8) . ?
C4 H4A 0.9300 . ?
C4 C5 1.365(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.508(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.527(6) . ?
C9 H9 0.9800 . ?
C9 C10 1.509(6) . ?
C9 C12 1.531(6) . ?
C11 H11 0.9800 . ?
C11 C12 1.532(6) . ?
C12 H12 0.9800 . ?
C12 C14 1.535(6) . ?
C13 C14 1.515(6) . ?
C13 C16 1.385(6) . ?
C13 C20 1.385(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 H16 0.9300 . ?
C16 C17 1.375(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.372(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(7) . ?
C20 H20 0.9300 . ?
O5 C27 1.211(5) . ?
O6 C30 1.207(5) . ?
O7 C30 1.348(5) . ?
O7 C31 1.462(5) . ?
O8 H8 0.8200 . ?
O8 C31 1.379(5) . ?
C21 C22 1.372(6) . ?
C21 C26 1.395(6) . ?
C21 C27 1.490(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.383(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.374(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.374(7) . ?
C25 H25 0.9300 . ?
C25 C26 1.378(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.496(6) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.529(6) . ?
C29 H29 0.9800 . ?
C29 C30 1.509(6) . ?
C29 C32 1.534(6) . ?
C31 H31 0.9800 . ?
C31 C32 1.526(6) . ?
C32 H32 0.9800 . ?
C32 C33 1.523(6) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.516(6) . ?
C34 C35 1.357(6) . ?
C34 C39 1.375(7) . ?
C35 H35 0.9300 . ?
C35 C36 1.390(7) . ?
C36 H36 0.9300 . ?
C36 C37 1.366(8) . ?
C37 H37 0.9300 . ?
C37 C38 1.347(8) . ?
C38 H38 0.9300 . ?
C38 C39 1.383(8) . ?
C39 H39 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O3 C11 110.2(4) . . ?
C11 O4 H4 109.5 . . ?
C2 C1 C7 118.5(4) . . ?
C6 C1 C2 118.7(4) . . ?
C6 C1 C7 122.8(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(5) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(5) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4A 120.1 . . ?
C3 C4 C5 119.8(5) . . ?
C5 C4 H4A 120.1 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(5) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 120.9(5) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
O1 C7 C1 120.2(4) . . ?
O1 C7 C8 121.2(4) . . ?
C1 C7 C8 118.6(4) . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C7 C8 C9 113.3(4) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C8 C9 H9 107.8 . . ?
C8 C9 C12 119.3(3) . . ?
C10 C9 C8 110.4(4) . . ?
C10 C9 H9 107.8 . . ?
C10 C9 C12 103.2(4) . . ?
C12 C9 H9 107.8 . . ?
O2 C10 O3 120.9(4) . . ?
O2 C10 C9 128.8(4) . . ?
O3 C10 C9 110.3(4) . . ?
O3 C11 H11 110.5 . . ?
O3 C11 C12 104.9(3) . . ?
O4 C11 O3 109.3(3) . . ?
O4 C11 H11 110.5 . . ?
O4 C11 C12 110.9(4) . . ?
C12 C11 H11 110.5 . . ?
C9 C12 C11 101.9(3) . . ?
C9 C12 H12 109.2 . . ?
C9 C12 C14 115.0(4) . . ?
C11 C12 H12 109.2 . . ?
C11 C12 C14 112.1(4) . . ?
C14 C12 H12 109.2 . . ?
C16 C13 C14 122.6(4) . . ?
C16 C13 C20 117.4(5) . . ?
C20 C13 C14 120.0(4) . . ?
C12 C14 H14A 109.3 . . ?
C12 C14 H14B 109.3 . . ?
C13 C14 C12 111.5(4) . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C13 C16 H16 119.3 . . ?
C17 C16 C13 121.5(5) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(5) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.7(5) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.7(5) . . ?
C20 C19 H19 120.1 . . ?
C13 C20 H20 119.2 . . ?
C19 C20 C13 121.6(5) . . ?
C19 C20 H20 119.2 . . ?
C30 O7 C31 110.0(3) . . ?
C31 O8 H8 109.5 . . ?
C22 C21 C26 118.4(4) . . ?
C22 C21 C27 123.1(4) . . ?
C26 C21 C27 118.5(4) . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.7(4) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.1(5) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.3(5) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 120.3 . . ?
C24 C25 C26 119.3(5) . . ?
C26 C25 H25 120.3 . . ?
C21 C26 H26 119.4 . . ?
C25 C26 C21 121.1(4) . . ?
C25 C26 H26 119.4 . . ?
O5 C27 C21 119.7(4) . . ?
O5 C27 C28 121.1(4) . . ?
C21 C27 C28 119.1(4) . . ?
C27 C28 H28A 109.0 . . ?
C27 C28 H28B 109.0 . . ?
C27 C28 C29 113.1(4) . . ?
H28A C28 H28B 107.8 . . ?
C29 C28 H28A 109.0 . . ?
C29 C28 H28B 109.0 . . ?
C28 C29 H29 107.6 . . ?
C28 C29 C32 119.7(4) . . ?
C30 C29 C28 110.9(4) . . ?
C30 C29 H29 107.6 . . ?
C30 C29 C32 103.0(4) . . ?
C32 C29 H29 107.6 . . ?
O6 C30 O7 120.9(4) . . ?
O6 C30 C29 128.5(5) . . ?
O7 C30 C29 110.6(4) . . ?
O7 C31 H31 110.6 . . ?
O7 C31 C32 105.1(3) . . ?
O8 C31 O7 109.8(4) . . ?
O8 C31 H31 110.6 . . ?
O8 C31 C32 109.9(4) . . ?
C32 C31 H31 110.6 . . ?
C29 C32 H32 109.7 . . ?
C31 C32 C29 102.2(3) . . ?
C31 C32 H32 109.7 . . ?
C33 C32 C29 113.7(4) . . ?
C33 C32 C31 111.7(4) . . ?
C33 C32 H32 109.7 . . ?
C32 C33 H33A 108.4 . . ?
C32 C33 H33B 108.4 . . ?
H33A C33 H33B 107.5 . . ?
C34 C33 C32 115.6(4) . . ?
C34 C33 H33A 108.4 . . ?
C34 C33 H33B 108.4 . . ?
C35 C34 C33 123.0(5) . . ?
C35 C34 C39 117.4(5) . . ?
C39 C34 C33 119.5(5) . . ?
C34 C35 H35 118.8 . . ?
C34 C35 C36 122.4(5) . . ?
C36 C35 H35 118.8 . . ?
C35 C36 H36 120.4 . . ?
C37 C36 C35 119.2(6) . . ?
C37 C36 H36 120.4 . . ?
C36 C37 H37 120.5 . . ?
C38 C37 C36 119.1(6) . . ?
C38 C37 H37 120.5 . . ?
C37 C38 H38 119.2 . . ?
C37 C38 C39 121.6(6) . . ?
C39 C38 H38 119.2 . . ?
C34 C39 C38 120.3(6) . . ?
C34 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C8 C9 3.5(6) . . . . ?
O3 C11 C12 C9 -30.0(4) . . . . ?
O3 C11 C12 C14 93.4(4) . . . . ?
O4 C11 C12 C9 87.9(4) . . . . ?
O4 C11 C12 C14 -148.7(4) . . . . ?
C1 C2 C3 C4 0.2(10) . . . . ?
C1 C7 C8 C9 -177.4(4) . . . . ?
C2 C1 C6 C5 -0.3(8) . . . . ?
C2 C1 C7 O1 -7.3(7) . . . . ?
C2 C1 C7 C8 173.6(4) . . . . ?
C2 C3 C4 C5 -0.5(10) . . . . ?
C3 C4 C5 C6 0.4(9) . . . . ?
C4 C5 C6 C1 0.0(9) . . . . ?
C6 C1 C2 C3 0.2(8) . . . . ?
C6 C1 C7 O1 174.1(5) . . . . ?
C6 C1 C7 C8 -5.0(7) . . . . ?
C7 C1 C2 C3 -178.5(5) . . . . ?
C7 C1 C6 C5 178.3(5) . . . . ?
C7 C8 C9 C10 -177.7(4) . . . . ?
C7 C8 C9 C12 63.0(5) . . . . ?
C8 C9 C10 O2 36.2(7) . . . . ?
C8 C9 C10 O3 -144.6(4) . . . . ?
C8 C9 C12 C11 150.2(4) . . . . ?
C8 C9 C12 C14 28.8(6) . . . . ?
C9 C12 C14 C13 -170.7(4) . . . . ?
C10 O3 C11 O4 -97.3(4) . . . . ?
C10 O3 C11 C12 21.7(5) . . . . ?
C10 C9 C12 C11 27.4(4) . . . . ?
C10 C9 C12 C14 -94.0(4) . . . . ?
C11 O3 C10 O2 175.7(4) . . . . ?
C11 O3 C10 C9 -3.6(5) . . . . ?
C11 C12 C14 C13 73.6(5) . . . . ?
C12 C9 C10 O2 164.9(5) . . . . ?
C12 C9 C10 O3 -16.0(5) . . . . ?
C13 C16 C17 C18 0.2(8) . . . . ?
C14 C13 C16 C17 -179.9(4) . . . . ?
C14 C13 C20 C19 179.7(4) . . . . ?
C16 C13 C14 C12 -93.9(5) . . . . ?
C16 C13 C20 C19 0.8(7) . . . . ?
C16 C17 C18 C19 1.1(8) . . . . ?
C17 C18 C19 C20 -1.3(8) . . . . ?
C18 C19 C20 C13 0.3(7) . . . . ?
C20 C13 C14 C12 87.3(5) . . . . ?
C20 C13 C16 C17 -1.1(7) . . . . ?
O5 C27 C28 C29 -1.4(7) . . . . ?
O7 C31 C32 C29 -29.3(5) . . . . ?
O7 C31 C32 C33 92.6(4) . . . . ?
O8 C31 C32 C29 88.8(4) . . . . ?
O8 C31 C32 C33 -149.3(4) . . . . ?
C21 C22 C23 C24 0.5(8) . . . . ?
C21 C27 C28 C29 179.3(4) . . . . ?
C22 C21 C26 C25 -0.4(7) . . . . ?
C22 C21 C27 O5 171.2(5) . . . . ?
C22 C21 C27 C28 -9.5(7) . . . . ?
C22 C23 C24 C25 -1.8(8) . . . . ?
C23 C24 C25 C26 2.0(8) . . . . ?
C24 C25 C26 C21 -0.9(8) . . . . ?
C26 C21 C22 C23 0.6(7) . . . . ?
C26 C21 C27 O5 -7.9(7) . . . . ?
C26 C21 C27 C28 171.4(4) . . . . ?
C27 C21 C22 C23 -178.4(4) . . . . ?
C27 C21 C26 C25 178.7(4) . . . . ?
C27 C28 C29 C30 -174.7(4) . . . . ?
C27 C28 C29 C32 65.7(6) . . . . ?
C28 C29 C30 O6 35.0(7) . . . . ?
C28 C29 C30 O7 -145.2(4) . . . . ?
C28 C29 C32 C31 150.5(4) . . . . ?
C28 C29 C32 C33 30.0(6) . . . . ?
C29 C32 C33 C34 175.6(4) . . . . ?
C30 O7 C31 O8 -97.2(4) . . . . ?
C30 O7 C31 C32 20.9(5) . . . . ?
C30 C29 C32 C31 27.0(5) . . . . ?
C30 C29 C32 C33 -93.5(4) . . . . ?
C31 O7 C30 O6 176.9(4) . . . . ?
C31 O7 C30 C29 -2.9(5) . . . . ?
C31 C32 C33 C34 60.5(5) . . . . ?
C32 C29 C30 O6 164.2(5) . . . . ?
C32 C29 C30 O7 -16.0(5) . . . . ?
C32 C33 C34 C35 38.5(7) . . . . ?
C32 C33 C34 C39 -143.6(5) . . . . ?
C33 C34 C35 C36 177.7(5) . . . . ?
C33 C34 C39 C38 -177.5(5) . . . . ?
C34 C35 C36 C37 -0.7(10) . . . . ?
C35 C34 C39 C38 0.5(9) . . . . ?
C35 C36 C37 C38 1.3(10) . . . . ?
C36 C37 C38 C39 -1.1(10) . . . . ?
C37 C38 C39 C34 0.1(10) . . . . ?
C39 C34 C35 C36 -0.3(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
