# 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_140926_wjp2014_9_3_cw_2
_database_code_depnum_ccdc_archive 'CCDC 1430093'
_audit_update_record             
;
2015-10-07 deposited with the CCDC.
2015-12-01 downloaded from the CCDC.
;
_audit_creation_date             2014-09-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            
'Methyl 2-(4-bromophenyl)-4,5-diphenylfuran-3-carboxylate'
_chemical_name_systematic        wip2014-9-3
_chemical_formula_moiety         'C24 H17 Br O3'
_chemical_formula_sum            'C24 H17 Br O3'
_chemical_formula_weight         433.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 Br1'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.7030(6)
_cell_length_b                   10.0809(10)
_cell_length_c                   11.7856(9)
_cell_angle_alpha                68.569(8)
_cell_angle_beta                 80.101(6)
_cell_angle_gamma                67.458(8)
_cell_volume                     990.44(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1943
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5861
_cell_measurement_theta_min      3.4075
_exptl_absorpt_coefficient_mu    2.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6231
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.41
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0097406000
_diffrn_orient_matrix_UB_12      0.0674188000
_diffrn_orient_matrix_UB_13      0.0115271000
_diffrn_orient_matrix_UB_21      0.0513665000
_diffrn_orient_matrix_UB_22      0.0167942000
_diffrn_orient_matrix_UB_23      -0.0488260000
_diffrn_orient_matrix_UB_31      -0.0594946000
_diffrn_orient_matrix_UB_32      0.0410060000
_diffrn_orient_matrix_UB_33      -0.0408538000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2846
_reflns_number_total             3617
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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         0.375
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3617
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0290P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0879
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_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
Br1 Br 0.18041(3) 0.48905(4) 0.47717(3) 0.05771(14) Uani 1 d . . .
O1 O 0.86538(19) 0.4784(2) 0.22121(16) 0.0391(5) Uani 1 d . . .
O2 O 1.0810(2) -0.0362(2) 0.3808(2) 0.0569(6) Uani 1 d . . .
O3 O 0.8402(2) 0.0406(2) 0.34358(19) 0.0483(6) Uani 1 d . . .
C1 C 1.0152(3) 0.4313(3) 0.1877(2) 0.0363(7) Uani 1 d . . .
C2 C 1.0740(3) 0.2774(3) 0.2244(2) 0.0349(6) Uani 1 d . . .
C3 C 0.9521(3) 0.2251(3) 0.2837(2) 0.0328(6) Uani 1 d . . .
C4 C 0.8294(3) 0.3499(3) 0.2807(2) 0.0353(7) Uani 1 d . . .
C5 C 0.6739(3) 0.3816(3) 0.3279(2) 0.0349(6) Uani 1 d . . .
C6 C 0.5600(3) 0.5077(4) 0.2623(3) 0.0457(8) Uani 1 d . . .
H6 H 0.5829 0.5712 0.1876 0.055 Uiso 1 calc . . R
C7 C 0.4134(3) 0.5406(4) 0.3059(3) 0.0469(8) Uani 1 d . . .
H7 H 0.3381 0.6255 0.2615 0.056 Uiso 1 calc . . R
C8 C 0.3812(3) 0.4453(3) 0.4163(3) 0.0382(7) Uani 1 d . . .
C9 C 0.4910(3) 0.3208(3) 0.4834(3) 0.0424(7) Uani 1 d . . .
H9 H 0.4672 0.2579 0.5582 0.051 Uiso 1 calc . . R
C10 C 0.6374(3) 0.2892(3) 0.4394(2) 0.0406(7) Uani 1 d . . .
H10 H 0.7122 0.2050 0.4850 0.049 Uiso 1 calc . . R
C11 C 1.0745(3) 0.5554(3) 0.1265(2) 0.0393(7) Uani 1 d . . .
C12 C 1.0100(4) 0.6898(4) 0.1520(3) 0.0517(8) Uani 1 d . . .
H12 H 0.9273 0.7024 0.2057 0.062 Uiso 1 calc . . R
C13 C 1.0672(4) 0.8063(4) 0.0984(3) 0.0635(10) Uani 1 d . . .
H13 H 1.0234 0.8967 0.1162 0.076 Uiso 1 calc . . R
C14 C 1.1892(4) 0.7874(4) 0.0189(3) 0.0615(10) Uani 1 d . . .
H14 H 1.2278 0.8653 -0.0171 0.074 Uiso 1 calc . . R
C15 C 1.2538(4) 0.6554(4) -0.0076(3) 0.0581(10) Uani 1 d . . .
H15 H 1.3363 0.6436 -0.0614 0.070 Uiso 1 calc . . R
C16 C 1.1971(3) 0.5386(4) 0.0454(3) 0.0482(8) Uani 1 d . . .
H16 H 1.2411 0.4490 0.0266 0.058 Uiso 1 calc . . R
C17 C 1.2310(3) 0.1819(3) 0.2100(2) 0.0358(7) Uani 1 d . . .
C18 C 1.3449(3) 0.1992(4) 0.2536(3) 0.0492(8) Uani 1 d . . .
H18 H 1.3222 0.2720 0.2913 0.059 Uiso 1 calc . . R
C19 C 1.4916(3) 0.1094(5) 0.2414(3) 0.0622(10) Uani 1 d . . .
H19 H 1.5670 0.1233 0.2699 0.075 Uiso 1 calc . . R
C20 C 1.5269(4) 0.0006(5) 0.1883(3) 0.0677(11) Uani 1 d . . .
H20 H 1.6259 -0.0603 0.1811 0.081 Uiso 1 calc . . R
C21 C 1.4147(4) -0.0188(4) 0.1450(3) 0.0636(10) Uani 1 d . . .
H21 H 1.4380 -0.0934 0.1091 0.076 Uiso 1 calc . . R
C22 C 1.2687(3) 0.0724(4) 0.1550(3) 0.0502(8) Uani 1 d . . .
H22 H 1.1941 0.0601 0.1242 0.060 Uiso 1 calc . . R
C23 C 0.9675(3) 0.0639(3) 0.3406(2) 0.0373(7) Uani 1 d . . .
C24 C 0.8421(4) -0.1123(4) 0.4130(3) 0.0621(10) Uani 1 d . . .
H24A H 0.9176 -0.1834 0.3787 0.093 Uiso 1 calc . . GR
H24B H 0.7464 -0.1182 0.4099 0.093 Uiso 1 calc . . GR
H24C H 0.8634 -0.1365 0.4962 0.093 Uiso 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
Br1 C8 1.896(3) . ?
O1 C1 1.381(3) . ?
O1 C4 1.375(3) . ?
O2 C23 1.198(3) . ?
O3 C23 1.336(3) . ?
O3 C24 1.452(3) . ?
C1 C2 1.355(4) . ?
C1 C11 1.471(4) . ?
C2 C3 1.446(3) . ?
C2 C17 1.477(4) . ?
C3 C4 1.355(4) . ?
C3 C23 1.470(4) . ?
C4 C5 1.469(4) . ?
C5 C6 1.391(4) . ?
C5 C10 1.385(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.375(4) . ?
C8 C9 1.370(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(4) . ?
C11 C16 1.390(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.363(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.387(4) . ?
C17 C22 1.379(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.361(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.382(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.374(5) . ?
C22 H22 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
C4 O1 C1 107.3(2) . . ?
C23 O3 C24 115.5(2) . . ?
O1 C1 C11 114.6(3) . . ?
C2 C1 O1 110.1(2) . . ?
C2 C1 C11 135.2(3) . . ?
C1 C2 C3 105.9(2) . . ?
C1 C2 C17 127.3(2) . . ?
C3 C2 C17 126.8(3) . . ?
C2 C3 C23 124.1(2) . . ?
C4 C3 C2 107.3(2) . . ?
C4 C3 C23 128.5(2) . . ?
O1 C4 C5 113.7(2) . . ?
C3 C4 O1 109.4(2) . . ?
C3 C4 C5 136.9(2) . . ?
C6 C5 C4 120.5(2) . . ?
C10 C5 C4 121.1(2) . . ?
C10 C5 C6 118.3(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 120.7 . . ?
C8 C7 C6 118.6(3) . . ?
C8 C7 H7 120.7 . . ?
C7 C8 Br1 119.1(2) . . ?
C9 C8 Br1 119.5(2) . . ?
C9 C8 C7 121.4(3) . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C5 C10 H10 119.6 . . ?
C9 C10 C5 120.7(3) . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C1 119.7(3) . . ?
C12 C11 C16 119.1(3) . . ?
C16 C11 C1 121.2(3) . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.5(4) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.3(3) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 120.0 . . ?
C15 C16 C11 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C2 120.3(3) . . ?
C22 C17 C2 121.6(2) . . ?
C22 C17 C18 118.1(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.2 . . ?
C19 C20 C21 119.6(3) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.9(4) . . ?
C22 C21 H21 120.1 . . ?
C17 C22 H22 119.4 . . ?
C21 C22 C17 121.2(3) . . ?
C21 C22 H22 119.4 . . ?
O2 C23 O3 123.2(3) . . ?
O2 C23 C3 124.2(2) . . ?
O3 C23 C3 112.7(2) . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C8 C9 C10 -179.7(2) . . . . ?
O1 C1 C2 C3 0.7(3) . . . . ?
O1 C1 C2 C17 -177.9(2) . . . . ?
O1 C1 C11 C12 28.2(4) . . . . ?
O1 C1 C11 C16 -153.4(2) . . . . ?
O1 C4 C5 C6 36.7(4) . . . . ?
O1 C4 C5 C10 -141.9(3) . . . . ?
C1 O1 C4 C3 -0.7(3) . . . . ?
C1 O1 C4 C5 177.0(2) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C1 C2 C3 C23 -178.2(3) . . . . ?
C1 C2 C17 C18 54.9(4) . . . . ?
C1 C2 C17 C22 -126.0(3) . . . . ?
C1 C11 C12 C13 177.8(3) . . . . ?
C1 C11 C16 C15 -177.7(3) . . . . ?
C2 C1 C11 C12 -148.7(3) . . . . ?
C2 C1 C11 C16 29.6(5) . . . . ?
C2 C3 C4 O1 1.1(3) . . . . ?
C2 C3 C4 C5 -175.9(3) . . . . ?
C2 C3 C23 O2 26.4(5) . . . . ?
C2 C3 C23 O3 -154.1(2) . . . . ?
C2 C17 C18 C19 179.4(3) . . . . ?
C2 C17 C22 C21 -178.2(3) . . . . ?
C3 C2 C17 C18 -123.4(3) . . . . ?
C3 C2 C17 C22 55.7(4) . . . . ?
C3 C4 C5 C6 -146.4(3) . . . . ?
C3 C4 C5 C10 34.9(5) . . . . ?
C4 O1 C1 C2 0.0(3) . . . . ?
C4 O1 C1 C11 -177.7(2) . . . . ?
C4 C3 C23 O2 -150.2(3) . . . . ?
C4 C3 C23 O3 29.4(4) . . . . ?
C4 C5 C6 C7 -179.1(3) . . . . ?
C4 C5 C10 C9 179.4(3) . . . . ?
C5 C6 C7 C8 -0.3(5) . . . . ?
C6 C5 C10 C9 0.8(4) . . . . ?
C6 C7 C8 Br1 -180.0(2) . . . . ?
C6 C7 C8 C9 0.8(5) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C8 C9 C10 C5 -0.3(4) . . . . ?
C10 C5 C6 C7 -0.4(4) . . . . ?
C11 C1 C2 C3 177.7(3) . . . . ?
C11 C1 C2 C17 -0.9(5) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C12 C11 C16 C15 0.7(4) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
C13 C14 C15 C16 0.1(5) . . . . ?
C14 C15 C16 C11 -0.5(5) . . . . ?
C16 C11 C12 C13 -0.6(5) . . . . ?
C17 C2 C3 C4 177.5(3) . . . . ?
C17 C2 C3 C23 0.3(4) . . . . ?
C17 C18 C19 C20 -1.0(5) . . . . ?
C18 C17 C22 C21 0.9(4) . . . . ?
C18 C19 C20 C21 0.7(5) . . . . ?
C19 C20 C21 C22 0.5(5) . . . . ?
C20 C21 C22 C17 -1.3(5) . . . . ?
C22 C17 C18 C19 0.2(4) . . . . ?
C23 C3 C4 O1 178.1(3) . . . . ?
C23 C3 C4 C5 1.2(5) . . . . ?
C24 O3 C23 O2 7.5(4) . . . . ?
C24 O3 C23 C3 -172.1(3) . . . . ?

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

data_140714_wjp2014_7_4_och3
_database_code_depnum_ccdc_archive 'CCDC 1430604'
_audit_update_record             
;
2015-10-11 deposited with the CCDC.
2015-12-01 downloaded from the CCDC.
;
_audit_creation_date             2014-07-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            
'Ethyl 4-(4-methoxyphenyl)-6-methyl-2-oxo-3-phenyl-2H-pyran-5-carboxylate'
_chemical_name_systematic        wjp2014-7-4-OCH3
_chemical_formula_moiety         'C22 H20 O5'
_chemical_formula_sum            'C22 H20 O5'
_chemical_formula_weight         364.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   10.9313(6)
_cell_length_b                   18.7544(11)
_cell_length_c                   9.2937(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.181(6)
_cell_angle_gamma                90.00
_cell_volume                     1838.82(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2000
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5153
_cell_measurement_theta_min      3.1365
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7257
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.14
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0131298000
_diffrn_orient_matrix_UB_12      -0.0139347000
_diffrn_orient_matrix_UB_13      0.0653052000
_diffrn_orient_matrix_UB_21      0.0216308000
_diffrn_orient_matrix_UB_22      0.0322022000
_diffrn_orient_matrix_UB_23      0.0382857000
_diffrn_orient_matrix_UB_31      -0.0622876000
_diffrn_orient_matrix_UB_32      0.0141383000
_diffrn_orient_matrix_UB_33      -0.0228010000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2386
_reflns_number_total             3355
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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         0.257
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0109(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0502P)²+0.5513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1313
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16),
 C17(H17)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_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 0.24412(14) 0.15887(10) -0.0388(2) 0.0697(5) Uani 1 d . . .
O2 O 0.40380(13) 0.16182(8) 0.16164(17) 0.0535(4) Uani 1 d . . .
O3 O 0.79658(17) 0.11529(13) 0.3530(2) 0.0941(7) Uani 1 d . . .
O4 O 0.81503(14) 0.18330(10) 0.16418(18) 0.0663(5) Uani 1 d . . .
O5 O 0.95683(13) 0.01779(9) -0.24405(17) 0.0595(4) Uani 1 d . . .
C1 C 0.3566(2) 0.15102(11) 0.0097(3) 0.0488(5) Uani 1 d . . .
C2 C 0.44651(18) 0.12962(10) -0.0733(2) 0.0421(5) Uani 1 d . . .
C3 C 0.57188(18) 0.12396(10) -0.0012(2) 0.0409(5) Uani 1 d . . .
C4 C 0.61384(18) 0.14176(11) 0.1559(2) 0.0440(5) Uani 1 d . . .
C5 C 0.5294(2) 0.15929(11) 0.2322(2) 0.0477(5) Uani 1 d . . .
C6 C 0.39120(18) 0.11442(11) -0.2342(2) 0.0448(5) Uani 1 d . . .
C7 C 0.31810(19) 0.16613(12) -0.3257(3) 0.0519(6) Uani 1 d . . .
H7 H 0.3057 0.2100 -0.2852 0.062 Uiso 1 calc . . R
C8 C 0.2642(2) 0.15355(14) -0.4738(3) 0.0622(7) Uani 1 d . . .
H8 H 0.2167 0.1890 -0.5330 0.075 Uiso 1 calc . . R
C9 C 0.2803(2) 0.08850(15) -0.5354(3) 0.0689(7) Uani 1 d . . .
H9 H 0.2436 0.0798 -0.6359 0.083 Uiso 1 calc . . R
C10 C 0.3510(2) 0.03664(14) -0.4473(3) 0.0663(7) Uani 1 d . . .
H10 H 0.3615 -0.0074 -0.4885 0.080 Uiso 1 calc . . R
C11 C 0.4068(2) 0.04910(12) -0.2980(3) 0.0550(6) Uani 1 d . . .
H11 H 0.4550 0.0136 -0.2397 0.066 Uiso 1 calc . . R
C12 C 0.66811(17) 0.09743(11) -0.0752(2) 0.0411(5) Uani 1 d . . .
C13 C 0.69871(19) 0.13225(11) -0.1915(2) 0.0471(5) Uani 1 d . . .
H13 H 0.6538 0.1730 -0.2308 0.057 Uiso 1 calc . . R
C14 C 0.79474(19) 0.10815(12) -0.2515(2) 0.0490(5) Uani 1 d . . .
H14 H 0.8147 0.1330 -0.3289 0.059 Uiso 1 calc . . R
C15 C 0.86088(18) 0.04662(12) -0.1952(2) 0.0445(5) Uani 1 d . . .
C16 C 0.82837(19) 0.00976(12) -0.0819(2) 0.0496(5) Uani 1 d . . .
H16 H 0.8700 -0.0325 -0.0464 0.059 Uiso 1 calc . . R
C17 C 0.73461(18) 0.03527(11) -0.0212(2) 0.0475(5) Uani 1 d . . .
H17 H 0.7154 0.0107 0.0570 0.057 Uiso 1 calc . . R
C18 C 1.0164(2) 0.06112(16) -0.3319(3) 0.0720(8) Uani 1 d . . .
H18A H 0.9569 0.0716 -0.4254 0.108 Uiso 1 calc . . GR
H18B H 1.0878 0.0361 -0.3496 0.108 Uiso 1 calc . . GR
H18C H 1.0447 0.1048 -0.2799 0.108 Uiso 1 calc . . GR
C19 C 0.7508(2) 0.14410(13) 0.2364(3) 0.0551(6) Uani 1 d . . .
C20 C 0.9530(2) 0.1819(2) 0.2235(4) 0.1055(12) Uani 1 d . . .
H20A H 0.9773 0.2106 0.3133 0.127 Uiso 1 calc . . R
H20B H 0.9811 0.1334 0.2491 0.127 Uiso 1 calc . . R
C21 C 1.0104(3) 0.2083(3) 0.1183(4) 0.1293(16) Uani 1 d . . .
H21A H 0.9884 0.1789 0.0308 0.194 Uiso 1 calc . . GR
H21B H 1.1007 0.2082 0.1587 0.194 Uiso 1 calc . . GR
H21C H 0.9818 0.2562 0.0925 0.194 Uiso 1 calc . . GR
C22 C 0.5532(2) 0.17874(14) 0.3923(3) 0.0628(7) Uani 1 d . . .
H22A H 0.4984 0.2174 0.4024 0.094 Uiso 1 calc . . GR
H22B H 0.6400 0.1931 0.4302 0.094 Uiso 1 calc . . GR
H22C H 0.5366 0.1383 0.4475 0.094 Uiso 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 1.203(2) . ?
O2 C1 1.386(3) . ?
O2 C5 1.359(3) . ?
O3 C19 1.198(3) . ?
O4 C19 1.315(3) . ?
O4 C20 1.465(3) . ?
O5 C15 1.360(2) . ?
O5 C18 1.425(3) . ?
C1 C2 1.455(3) . ?
C2 C3 1.363(3) . ?
C2 C6 1.487(3) . ?
C3 C4 1.450(3) . ?
C3 C12 1.486(3) . ?
C4 C5 1.344(3) . ?
C4 C19 1.489(3) . ?
C5 C22 1.487(3) . ?
C6 C7 1.395(3) . ?
C6 C11 1.390(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.369(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.378(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.372(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(3) . ?
C12 C17 1.396(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(3) . ?
C15 C16 1.382(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.384(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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 O2 C1 123.12(16) . . ?
C19 O4 C20 115.7(2) . . ?
C15 O5 C18 118.23(18) . . ?
O1 C1 O2 115.78(19) . . ?
O1 C1 C2 127.0(2) . . ?
O2 C1 C2 117.21(17) . . ?
C1 C2 C6 115.63(17) . . ?
C3 C2 C1 119.51(19) . . ?
C3 C2 C6 124.85(17) . . ?
C2 C3 C4 119.31(17) . . ?
C2 C3 C12 122.75(18) . . ?
C4 C3 C12 117.90(16) . . ?
C3 C4 C19 121.60(17) . . ?
C5 C4 C3 120.52(18) . . ?
C5 C4 C19 117.8(2) . . ?
O2 C5 C22 111.35(18) . . ?
C4 C5 O2 120.0(2) . . ?
C4 C5 C22 128.6(2) . . ?
C7 C6 C2 119.79(19) . . ?
C11 C6 C2 122.32(19) . . ?
C11 C6 C7 117.9(2) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.3(2) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.1(2) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.5(2) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.7(2) . . ?
C11 C10 H10 119.6 . . ?
C6 C11 H11 119.8 . . ?
C10 C11 C6 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C3 123.49(18) . . ?
C13 C12 C17 117.90(18) . . ?
C17 C12 C3 118.56(17) . . ?
C12 C13 H13 119.1 . . ?
C12 C13 C14 121.74(19) . . ?
C14 C13 H13 119.1 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.54(19) . . ?
C15 C14 H14 120.2 . . ?
O5 C15 C14 125.12(19) . . ?
O5 C15 C16 115.50(19) . . ?
C16 C15 C14 119.38(18) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.35(19) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 121.04(19) . . ?
C16 C17 H17 119.5 . . ?
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 . . ?
O3 C19 O4 124.2(2) . . ?
O3 C19 C4 124.6(2) . . ?
O4 C19 C4 111.18(19) . . ?
O4 C20 H20A 109.7 . . ?
O4 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C21 C20 O4 109.9(3) . . ?
C21 C20 H20A 109.7 . . ?
C21 C20 H20B 109.7 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C5 C22 H22A 109.5 . . ?
C5 C22 H22B 109.5 . . ?
C5 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.3(2) . . . . ?
O1 C1 C2 C6 -1.6(3) . . . . ?
O2 C1 C2 C3 -2.6(3) . . . . ?
O2 C1 C2 C6 176.55(17) . . . . ?
O5 C15 C16 C17 178.27(19) . . . . ?
C1 O2 C5 C4 -3.8(3) . . . . ?
C1 O2 C5 C22 175.29(18) . . . . ?
C1 C2 C3 C4 -2.1(3) . . . . ?
C1 C2 C3 C12 175.44(18) . . . . ?
C1 C2 C6 C7 55.6(2) . . . . ?
C1 C2 C6 C11 -122.8(2) . . . . ?
C2 C3 C4 C5 4.2(3) . . . . ?
C2 C3 C4 C19 -173.33(19) . . . . ?
C2 C3 C12 C13 64.5(3) . . . . ?
C2 C3 C12 C17 -117.9(2) . . . . ?
C2 C6 C7 C8 -179.04(19) . . . . ?
C2 C6 C11 C10 178.36(19) . . . . ?
C3 C2 C6 C7 -125.3(2) . . . . ?
C3 C2 C6 C11 56.4(3) . . . . ?
C3 C4 C5 O2 -1.3(3) . . . . ?
C3 C4 C5 C22 179.7(2) . . . . ?
C3 C4 C19 O3 -130.7(3) . . . . ?
C3 C4 C19 O4 50.6(3) . . . . ?
C3 C12 C13 C14 175.85(19) . . . . ?
C3 C12 C17 C16 -177.46(19) . . . . ?
C4 C3 C12 C13 -117.9(2) . . . . ?
C4 C3 C12 C17 59.7(3) . . . . ?
C5 O2 C1 O1 -175.92(19) . . . . ?
C5 O2 C1 C2 5.8(3) . . . . ?
C5 C4 C19 O3 51.7(3) . . . . ?
C5 C4 C19 O4 -127.0(2) . . . . ?
C6 C2 C3 C4 178.81(18) . . . . ?
C6 C2 C3 C12 -3.6(3) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C7 C6 C11 C10 0.0(3) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C9 C10 C11 C6 0.5(3) . . . . ?
C11 C6 C7 C8 -0.6(3) . . . . ?
C12 C3 C4 C5 -173.45(19) . . . . ?
C12 C3 C4 C19 9.0(3) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
C13 C12 C17 C16 0.3(3) . . . . ?
C13 C14 C15 O5 -179.8(2) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
C14 C15 C16 C17 -2.6(3) . . . . ?
C15 C16 C17 C12 1.9(3) . . . . ?
C17 C12 C13 C14 -1.8(3) . . . . ?
C18 O5 C15 C14 16.5(3) . . . . ?
C18 O5 C15 C16 -164.4(2) . . . . ?
C19 O4 C20 C21 163.8(3) . . . . ?
C19 C4 C5 O2 176.33(19) . . . . ?
C19 C4 C5 C22 -2.6(3) . . . . ?
C20 O4 C19 O3 8.8(4) . . . . ?
C20 O4 C19 C4 -172.5(2) . . . . ?

####################################################################### 
# 
# 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_151012_wjp2014_10_9_cw
_database_code_depnum_ccdc_archive 'CCDC 1432392'
_audit_update_record             
;
2015-10-21 deposited with the CCDC.
2015-12-01 downloaded from the CCDC.
;
_audit_creation_date             2015-10-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            wjp2014_10_9
_chemical_name_systematic        
'tert-butyl 2-methyl-5-phenyl-4-(thiophen-2-yl)furan-3-carboxylate'
_chemical_formula_moiety         'C20 H20 O3 S'
_chemical_formula_sum            'C20 H20 O3 S'
_chemical_formula_weight         340.42
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.2716(5)
_cell_length_b                   11.6329(6)
_cell_length_c                   17.2262(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1857.95(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2706
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5492
_cell_measurement_theta_min      3.0421
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12260
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.05
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0058238000
_diffrn_orient_matrix_UB_12      -0.0114713000
_diffrn_orient_matrix_UB_13      0.0403187000
_diffrn_orient_matrix_UB_21      -0.0752525000
_diffrn_orient_matrix_UB_22      0.0105332000
_diffrn_orient_matrix_UB_23      -0.0017728000
_diffrn_orient_matrix_UB_31      -0.0123171000
_diffrn_orient_matrix_UB_32      -0.0589713000
_diffrn_orient_matrix_UB_33      -0.0081713000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1461
_reflns_number_total             1947
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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         0.363
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(19)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         1947
_refine_ls_number_restraints     131
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.012
_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)+(0.0608P)²+0.3290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1175
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C11A-C12A
 1.4 with sigma of 0.02
 C13A-C12A
 1.4 with sigma of 0.02
 C14A-C13A
 1.5 with sigma of 0.02
 C11-C8
 1.5 with sigma of 0.02
 C11A-C8
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
S1 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim S1A \\sim C12A \\sim C13A
\\sim C14A \\sim C11A: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02
4. Others
 Sof(S1A)=Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=
 Sof(H14A)=1-FVAR(1)
 Sof(S1)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14),
 C12A(H12A), C13A(H13A), C14A(H14A)
5.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
;
_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 1.1852(3) 0.5870(2) 0.06365(13) 0.0644(6) Uani 1 d A . .
O2 O 1.3401(3) 0.6125(3) 0.29439(16) 0.0895(8) Uani 1 d A . .
O3 O 1.1368(3) 0.7161(2) 0.30848(14) 0.0681(6) Uani 1 d A . .
C1 C 0.9964(5) 0.5987(4) -0.0603(2) 0.0852(12) Uani 1 d . . .
H1 H 1.0950 0.5917 -0.0688 0.102 Uiso 1 calc . . R
C2 C 0.9022(6) 0.5910(5) -0.1219(3) 0.1014(16) Uani 1 d . . .
H2 H 0.9383 0.5772 -0.1714 0.122 Uiso 1 calc . . R
C3 C 0.7573(5) 0.6034(4) -0.1117(3) 0.0825(12) Uani 1 d . . .
H3 H 0.6947 0.5997 -0.1539 0.099 Uiso 1 calc . . R
C4 C 0.7057(5) 0.6213(3) -0.0385(2) 0.0743(11) Uani 1 d . . .
H4 H 0.6069 0.6284 -0.0305 0.089 Uiso 1 calc . . R
C5 C 0.7985(4) 0.6291(3) 0.0237(2) 0.0698(10) Uani 1 d . . .
H5 H 0.7614 0.6428 0.0730 0.084 Uiso 1 calc . . R
C6 C 0.9459(4) 0.6168(3) 0.01425(19) 0.0559(8) Uani 1 d . . .
C7 C 1.0455(4) 0.6219(3) 0.07976(19) 0.0568(8) Uani 1 d A . .
C8 C 1.0365(3) 0.6509(3) 0.15624(19) 0.0527(8) Uani 1 d . . D
C9 C 1.1775(4) 0.6317(3) 0.18901(19) 0.0557(8) Uani 1 d A . .
C10 C 1.2627(4) 0.5938(3) 0.1302(2) 0.0640(9) Uani 1 d . . .
C15 C 1.2282(4) 0.6512(3) 0.2688(2) 0.0639(9) Uani 1 d . . .
C16 C 1.1593(5) 0.7469(3) 0.3905(2) 0.0727(10) Uani 1 d . . .
C17 C 1.2940(6) 0.8189(5) 0.3984(3) 0.121(2) Uani 1 d A . .
H17A H 1.2914 0.8805 0.3613 0.182 Uiso 1 calc . . GR
H17B H 1.3772 0.7718 0.3889 0.182 Uiso 1 calc . . GR
H17C H 1.2991 0.8502 0.4498 0.182 Uiso 1 calc . . GR
C18 C 1.1617(8) 0.6409(4) 0.4396(3) 0.1131(18) Uani 1 d A . .
H18A H 1.2449 0.5956 0.4267 0.170 Uiso 1 calc . . GR
H18B H 1.0760 0.5967 0.4302 0.170 Uiso 1 calc . . GR
H18C H 1.1658 0.6621 0.4934 0.170 Uiso 1 calc . . GR
C19 C 1.0258(6) 0.8190(5) 0.4074(3) 0.1076(17) Uani 1 d A . .
H19A H 0.9413 0.7716 0.4034 0.161 Uiso 1 calc . . GR
H19B H 1.0196 0.8807 0.3706 0.161 Uiso 1 calc . . GR
H19C H 1.0322 0.8500 0.4589 0.161 Uiso 1 calc . . GR
C20 C 1.4191(4) 0.5665(4) 0.1238(3) 0.0865(13) Uani 1 d A . .
H20A H 1.4651 0.6217 0.0906 0.130 Uiso 1 calc . . GR
H20B H 1.4307 0.4909 0.1022 0.130 Uiso 1 calc . . GR
H20C H 1.4625 0.5691 0.1743 0.130 Uiso 1 calc . . GR
S1 S 0.8633(2) 0.83613(17) 0.19101(17) 0.0828(8) Uani 0.682(5) d A 1 .
C11 C 0.9119(15) 0.6977(13) 0.1973(14) 0.066(2) Uani 0.682(5) d A 1 D
C12 C 0.810(2) 0.6392(12) 0.2425(12) 0.076(3) Uani 0.682(5) d A 1 .
H12 H 0.8119 0.5614 0.2547 0.091 Uiso 0.682(5) calc A 1 R
C13 C 0.6949(10) 0.7243(8) 0.2682(5) 0.074(2) Uani 0.682(5) d A 1 .
H13 H 0.6156 0.7057 0.2989 0.089 Uiso 0.682(5) calc A 1 R
C14 C 0.7228(13) 0.8283(8) 0.2412(7) 0.083(2) Uani 0.682(5) d A 1 .
H14 H 0.6641 0.8914 0.2510 0.099 Uiso 0.682(5) calc A 1 R
S1A S 0.8058(13) 0.6093(7) 0.2504(7) 0.0801(18) Uani 0.318(5) d A 2 .
C11A C 0.897(4) 0.690(3) 0.194(3) 0.071(3) Uani 0.318(5) d A 2 D
C12A C 0.829(2) 0.8004(17) 0.1967(14) 0.078(3) Uani 0.318(5) d A 2 D
H12A H 0.8548 0.8645 0.1677 0.093 Uiso 0.318(5) calc A 2 R
C13A C 0.710(3) 0.795(2) 0.2529(15) 0.075(3) Uani 0.318(5) d A 2 D
H13A H 0.6531 0.8565 0.2687 0.089 Uiso 0.318(5) calc A 2 R
C14A C 0.698(3) 0.6784(15) 0.2796(14) 0.074(3) Uani 0.318(5) d A 2 D
H14A H 0.6259 0.6526 0.3127 0.089 Uiso 0.318(5) calc A 2 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 1.386(4) . ?
O1 C10 1.355(5) . ?
O2 C15 1.214(4) . ?
O3 C15 1.325(4) . ?
O3 C16 1.473(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.378(6) . ?
C1 C6 1.382(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.363(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(5) . ?
C6 C7 1.459(5) . ?
C7 C8 1.362(5) . ?
C8 C9 1.442(5) . ?
C8 C11 1.460(10) . ?
C8 C11A 1.514(18) . ?
C9 C10 1.358(5) . ?
C9 C15 1.470(5) . ?
C10 C20 1.489(5) . ?
C16 C17 1.510(6) . ?
C16 C18 1.496(5) . ?
C16 C19 1.523(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
S1 C11 1.675(14) . ?
S1 C14 1.565(10) . ?
C11 C12 1.40(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.520(19) . ?
C13 H13 0.9300 . ?
C13 C14 1.323(11) . ?
C14 H14 0.9300 . ?
S1A C11A 1.59(4) . ?
S1A C14A 1.38(2) . ?
C11A C12A 1.44(2) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.464(18) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.437(16) . ?
C14A H14A 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 O1 C7 108.0(3) . . ?
C15 O3 C16 122.9(3) . . ?
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.8(4) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(4) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.7(4) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.3(4) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 117.3(4) . . ?
C1 C6 C7 120.7(3) . . ?
C5 C6 C7 122.0(3) . . ?
O1 C7 C6 115.1(3) . . ?
C8 C7 O1 108.9(3) . . ?
C8 C7 C6 136.0(3) . . ?
C7 C8 C9 106.6(3) . . ?
C7 C8 C11 127.5(10) . . ?
C7 C8 C11A 123(2) . . ?
C9 C8 C11 125.8(10) . . ?
C9 C8 C11A 131(2) . . ?
C11 C8 C11A 6(3) . . ?
C8 C9 C15 129.2(3) . . ?
C10 C9 C8 106.6(3) . . ?
C10 C9 C15 124.2(3) . . ?
O1 C10 C9 110.0(3) . . ?
O1 C10 C20 116.2(4) . . ?
C9 C10 C20 133.7(4) . . ?
O2 C15 O3 124.8(4) . . ?
O2 C15 C9 123.8(3) . . ?
O3 C15 C9 111.4(3) . . ?
O3 C16 C17 109.8(3) . . ?
O3 C16 C18 110.1(3) . . ?
O3 C16 C19 101.7(3) . . ?
C17 C16 C19 110.5(4) . . ?
C18 C16 C17 113.2(4) . . ?
C18 C16 C19 111.0(4) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 S1 C11 97.6(6) . . ?
C8 C11 S1 122.7(11) . . ?
C12 C11 C8 128.5(12) . . ?
C12 C11 S1 108.7(8) . . ?
C11 C12 H12 125.7 . . ?
C11 C12 C13 108.6(9) . . ?
C13 C12 H12 125.7 . . ?
C12 C13 H13 124.6 . . ?
C14 C13 C12 110.8(9) . . ?
C14 C13 H13 124.6 . . ?
S1 C14 H14 122.9 . . ?
C13 C14 S1 114.3(7) . . ?
C13 C14 H14 122.9 . . ?
C14A S1A C11A 105.4(12) . . ?
C8 C11A S1A 123(2) . . ?
C12A C11A C8 131(3) . . ?
C12A C11A S1A 105.7(15) . . ?
C11A C12A H12A 125.8 . . ?
C11A C12A C13A 108.4(18) . . ?
C13A C12A H12A 125.8 . . ?
C12A C13A H13A 126.0 . . ?
C14A C13A C12A 108.1(19) . . ?
C14A C13A H13A 126.0 . . ?
S1A C14A C13A 112.2(18) . . ?
S1A C14A H14A 123.9 . . ?
C13A C14A H14A 123.9 . . ?

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 -0.5(4) . . . . ?
O1 C7 C8 C11 176.6(8) . . . . ?
O1 C7 C8 C11A -178.3(17) . . . . ?
C1 C2 C3 C4 -1.3(9) . . . . ?
C1 C6 C7 O1 -11.3(5) . . . . ?
C1 C6 C7 C8 170.5(4) . . . . ?
C2 C1 C6 C5 -1.3(7) . . . . ?
C2 C1 C6 C7 178.4(4) . . . . ?
C2 C3 C4 C5 1.2(8) . . . . ?
C3 C4 C5 C6 -1.2(7) . . . . ?
C4 C5 C6 C1 1.2(6) . . . . ?
C4 C5 C6 C7 -178.5(3) . . . . ?
C5 C6 C7 O1 168.4(3) . . . . ?
C5 C6 C7 C8 -9.7(6) . . . . ?
C6 C1 C2 C3 1.4(8) . . . . ?
C6 C7 C8 C9 177.7(4) . . . . ?
C6 C7 C8 C11 -5.2(10) . . . . ?
C6 C7 C8 C11A -0.1(18) . . . . ?
C7 O1 C10 C9 0.2(4) . . . . ?
C7 O1 C10 C20 -176.4(3) . . . . ?
C7 C8 C9 C10 0.6(4) . . . . ?
C7 C8 C9 C15 178.7(3) . . . . ?
C7 C8 C11 S1 -78.0(17) . . . . ?
C7 C8 C11 C12 97(2) . . . . ?
C7 C8 C11A S1A 105(4) . . . . ?
C7 C8 C11A C12A -83(5) . . . . ?
C8 C9 C10 O1 -0.5(4) . . . . ?
C8 C9 C10 C20 175.2(4) . . . . ?
C8 C9 C15 O2 165.4(4) . . . . ?
C8 C9 C15 O3 -14.7(5) . . . . ?
C8 C11 C12 C13 -176.0(18) . . . . ?
C8 C11A C12A C13A -170(5) . . . . ?
C9 C8 C11 S1 98.5(17) . . . . ?
C9 C8 C11 C12 -86(2) . . . . ?
C9 C8 C11A S1A -72(4) . . . . ?
C9 C8 C11A C12A 100(5) . . . . ?
C10 O1 C7 C6 -178.4(3) . . . . ?
C10 O1 C7 C8 0.2(4) . . . . ?
C10 C9 C15 O2 -16.8(6) . . . . ?
C10 C9 C15 O3 163.1(3) . . . . ?
C15 O3 C16 C17 63.6(5) . . . . ?
C15 O3 C16 C18 -61.7(5) . . . . ?
C15 O3 C16 C19 -179.4(3) . . . . ?
C15 C9 C10 O1 -178.7(3) . . . . ?
C15 C9 C10 C20 -3.0(7) . . . . ?
C16 O3 C15 O2 -1.5(6) . . . . ?
C16 O3 C15 C9 178.6(3) . . . . ?
S1 C11 C12 C13 0(2) . . . . ?
C11 C8 C9 C10 -176.5(8) . . . . ?
C11 C8 C9 C15 1.5(9) . . . . ?
C11 C8 C11A S1A -115(27) . . . . ?
C11 C8 C11A C12A 57(21) . . . . ?
C11 S1 C14 C13 -0.1(13) . . . . ?
C11 C12 C13 C14 0.0(19) . . . . ?
C12 C13 C14 S1 0.0(14) . . . . ?
C14 S1 C11 C8 176.3(16) . . . . ?
C14 S1 C11 C12 0.1(17) . . . . ?
S1A C11A C12A C13A 3(4) . . . . ?
C11A C8 C9 C10 178.1(19) . . . . ?
C11A C8 C9 C15 -3.8(19) . . . . ?
C11A C8 C11 S1 -121(26) . . . . ?
C11A C8 C11 C12 54(23) . . . . ?
C11A S1A C14A C13A -3(3) . . . . ?
C11A C12A C13A C14A -5(3) . . . . ?
C12A C13A C14A S1A 5(3) . . . . ?
C14A S1A C11A C8 173(4) . . . . ?
C14A S1A C11A C12A -1(4) . . . . ?

