# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_5a_sci64
_audit_creation_date             2014-02-20
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H20 O4'
_chemical_formula_sum            'C22 H20 O4'
_chemical_formula_weight         348.38
#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_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'

_symmetry_Int_Tables_number      14
_cell_length_a                   17.4674(16)
_cell_length_b                   22.482(2)
_cell_length_c                   9.5117(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.222(6)
_cell_angle_gamma                90
_cell_volume                     3735.2(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0605 before and 0.0395 after correction.
        The Ratio of minimum to maximum transmission is 0.8491.
        The λ/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             1472
#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_number            26640
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.166
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             6589
_reflns_number_gt                4331
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_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         0.188
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0070(5)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         6589
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.04
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0371P)²+4.0681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1601
#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1A(0.079) H1B(0.079) H6A(0.068) H6B(0.068) H7A(0.067) H7B(0.067)
 H9(0.073) H10(0.081) H11(0.082) H12(0.075) H14A(0.068) H14B(0.068) H15A(0.066)
 H15B(0.066) H17(0.071) H18(0.08) H19(0.085) H20(0.079) H22A(0.076) H22B(0.076)
 H23(0.088) H24(0.078) H26A(0.075) H26B(0.075) H27A(0.08) H27B(0.08)
 H30A(0.073) H30B(0.073) H31A(0.07) H31B(0.07) H32(0.095) H33(0.089)
 H35A(0.082) H35B(0.082) H36A(0.083) H36B(0.083) H41(0.08) H42(0.092)
 H43(0.098) H44(0.09)
 Fixed X: H1A(1.3035) H1B(1.231) H6A(1.0114) H6B(0.9935) H7A(0.8531)
 H7B(0.9377) H9(0.8366) H10(0.8059) H11(0.8297) H12(0.8852) H14A(0.957)
 H14B(0.8717) H15A(0.9244) H15B(0.9337) H17(0.9746) H18(1.0444) H19(1.1753)
 H20(1.2375) H22A(1.1927) H22B(1.1532) H23(0.5416) H24(0.4732) H26A(0.4312)
 H26B(0.4209) H27A(0.3694) H27B(0.4549) H30A(0.4408) H30B(0.3558) H31A(0.4948)
 H31B(0.511) H32(0.6743) H33(0.736) H35A(0.6518) H35B(0.6906) H36A(0.7315)
 H36B(0.8035) H41(0.3403) H42(0.3061) H43(0.3275) H44(0.3804)
 Fixed Y: H1A(0.8063) H1B(0.8107) H6A(0.7074) H6B(0.7756) H7A(0.7656)
 H7B(0.7868) H9(0.8014) H10(0.8893) H11(0.9782) H12(0.9788) H14A(0.9679)
 H14B(0.9552) H15A(0.8866) H15B(0.9547) H17(0.9009) H18(0.8863) H19(0.8838)
 H20(0.8956) H22A(0.9574) H22B(0.9002) H23(0.8848) H24(0.8986) H26A(0.9567)
 H26B(0.8888) H27A(0.9585) H27B(0.9708) H30A(0.7905) H30B(0.7694) H31A(0.7745)
 H31B(0.7063) H32(0.8849) H33(0.9014) H35A(0.905) H35B(0.9618) H36A(0.8152)
 H36B(0.8117) H41(0.8031) H42(0.8903) H43(0.9793) H44(0.9818)
 Fixed Z: H1A(-0.0143) H1B(-0.1115) H6A(0.5145) H6B(0.5242) H7A(0.2577)
 H7B(0.238) H9(0.5575) H10(0.6684) H11(0.5545) H12(0.3351) H14A(0.1377)
 H14B(0.094) H15A(-0.0784) H15B(-0.1126) H17(-0.3031) H18(-0.5064) H19(-0.4973)
 H20(-0.2877) H22A(-0.0123) H22B(0.0478) H23(1.4301) H24(1.2269) H26A(1.0378)
 H26B(1.0015) H27A(0.8306) H27B(0.7889) H30A(0.6864) H30B(0.6708) H31A(0.4006)
 H31B(0.4168) H32(1.4254) H33(1.2154) H35A(0.8796) H35B(0.9432) H36A(1.0397)
 H36B(0.9422) H41(0.3635) H42(0.2531) H43(0.3659) H44(0.5886)
;
#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
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
O1 O 0.92435(12) 0.73225(9) 0.3974(2) 0.0559(6) Uani 1 d . .
O2 O 0.92325(13) 0.88609(9) 0.1813(2) 0.0591(6) Uani 1 d . .
O3 O 1.02904(11) 0.91673(9) -0.0462(2) 0.0538(6) Uani 1 d . .
O4 O 1.25791(12) 0.88623(11) -0.0195(3) 0.0660(7) Uani 1 d . .
O5 O 0.52680(12) 0.91817(10) 0.9714(3) 0.0624(6) Uani 1 d . .
O6 O 0.42059(14) 0.88928(9) 0.7443(3) 0.0671(7) Uani 1 d . .
O7 O 0.42479(12) 0.73443(9) 0.5304(2) 0.0582(6) Uani 1 d . .
O8 O 0.75640(12) 0.89114(11) 0.9478(3) 0.0689(7) Uani 1 d . .
C1 C 1.25244(19) 0.82305(16) -0.0219(4) 0.0660(10) Uani 1 d . .
H1A H 1.3035 0.8063 -0.0143 0.079 Uiso 1 calc . .
H1B H 1.231 0.8107 -0.1115 0.079 Uiso 1 calc . .
C2 C 1.20491(19) 0.79920(16) 0.0917(4) 0.0638(9) Uani 1 d . .
C3 C 1.1606(2) 0.78369(16) 0.1781(4) 0.0619(9) Uani 1 d . .
C4 C 1.10641(19) 0.76711(16) 0.2760(4) 0.0601(9) Uani 1 d . .
C5 C 1.0578(2) 0.75443(15) 0.3585(4) 0.0595(9) Uani 1 d . .
C6 C 0.99732(19) 0.74221(15) 0.4600(3) 0.0566(8) Uani 1 d . .
H6A H 1.0114 0.7074 0.5145 0.068 Uiso 1 calc . .
H6B H 0.9935 0.7756 0.5242 0.068 Uiso 1 calc . .
C7 C 0.8985(2) 0.77899(13) 0.3075(3) 0.0556(8) Uani 1 d . .
H7A H 0.8531 0.7656 0.2577 0.067 Uiso 1 calc . .
H7B H 0.9377 0.7868 0.238 0.067 Uiso 1 calc . .
C8 C 0.88005(17) 0.83594(13) 0.3819(3) 0.0482(7) Uani 1 d . .
C9 C 0.84680(19) 0.83727(16) 0.5124(4) 0.0604(9) Uani 1 d . .
H9 H 0.8366 0.8014 0.5575 0.073 Uiso 1 calc . .
C10 C 0.8279(2) 0.88969(18) 0.5795(4) 0.0676(10) Uani 1 d . .
H10 H 0.8059 0.8893 0.6684 0.081 Uiso 1 calc . .
C11 C 0.8423(2) 0.94241(17) 0.5114(4) 0.0686(10) Uani 1 d . .
H11 H 0.8297 0.9782 0.5545 0.082 Uiso 1 calc . .
C12 C 0.8752(2) 0.94286(15) 0.3796(4) 0.0624(9) Uani 1 d . .
H12 H 0.8852 0.9788 0.3351 0.075 Uiso 1 calc . .
C13 C 0.89311(16) 0.89021(13) 0.3144(3) 0.0480(7) Uani 1 d . .
C14 C 0.92288(18) 0.93850(13) 0.0971(4) 0.0569(9) Uani 1 d . .
H14A H 0.957 0.9679 0.1377 0.068 Uiso 1 calc . .
H14B H 0.8717 0.9552 0.094 0.068 Uiso 1 calc . .
C15 C 0.94835(16) 0.92333(14) -0.0478(4) 0.0547(8) Uani 1 d . .
H15A H 0.9244 0.8866 -0.0784 0.066 Uiso 1 calc . .
H15B H 0.9337 0.9547 -0.1126 0.066 Uiso 1 calc . .
C16 C 1.06507(17) 0.90689(12) -0.1724(3) 0.0465(7) Uani 1 d . .
C17 C 1.02776(19) 0.89983(14) -0.2992(4) 0.0593(9) Uani 1 d . .
H17 H 0.9746 0.9009 -0.3031 0.071 Uiso 1 calc . .
C18 C 1.0695(2) 0.89113(16) -0.4208(4) 0.0669(10) Uani 1 d . .
H18 H 1.0444 0.8863 -0.5064 0.08 Uiso 1 calc . .
C19 C 1.1473(2) 0.88968(16) -0.4155(4) 0.0710(10) Uani 1 d . .
H19 H 1.1753 0.8838 -0.4973 0.085 Uiso 1 calc . .
C20 C 1.1843(2) 0.89686(15) -0.2897(4) 0.0661(10) Uani 1 d . .
H20 H 1.2375 0.8956 -0.2877 0.079 Uiso 1 calc . .
C21 C 1.14516(17) 0.90586(13) -0.1652(4) 0.0512(8) Uani 1 d . .
C22 C 1.18548(18) 0.91506(16) -0.0273(4) 0.0635(9) Uani 1 d . .
H22A H 1.1927 0.9574 -0.0123 0.076 Uiso 1 calc . .
H22B H 1.1532 0.9002 0.0478 0.076 Uiso 1 calc . .
C23 C 0.5671(2) 0.89071(16) 1.3456(4) 0.0736(11) Uani 1 d . .
H23 H 0.5416 0.8848 1.4301 0.088 Uiso 1 calc . .
C24 C 0.5264(2) 0.89901(15) 1.2244(4) 0.0647(9) Uani 1 d . .
H24 H 0.4732 0.8986 1.2269 0.078 Uiso 1 calc . .
C25 C 0.56361(18) 0.90805(13) 1.0975(4) 0.0534(8) Uani 1 d . .
C26 C 0.44535(17) 0.92550(15) 0.9723(4) 0.0627(9) Uani 1 d . .
H26A H 0.4312 0.9567 1.0378 0.075 Uiso 1 calc . .
H26B H 0.4209 0.8888 1.0015 0.075 Uiso 1 calc . .
C27 C 0.4204(2) 0.94151(15) 0.8283(4) 0.0669(10) Uani 1 d . .
H27A H 0.3694 0.9585 0.8306 0.08 Uiso 1 calc . .
H27B H 0.4549 0.9708 0.7889 0.08 Uiso 1 calc . .
C28 C 0.39162(18) 0.89281(15) 0.6097(4) 0.0568(8) Uani 1 d . .
C29 C 0.38119(17) 0.83876(14) 0.5426(3) 0.0513(8) Uani 1 d . .
C30 C 0.4005(2) 0.78221(14) 0.6188(4) 0.0605(9) Uani 1 d . .
H30A H 0.4408 0.7905 0.6864 0.073 Uiso 1 calc . .
H30B H 0.3558 0.7694 0.6708 0.073 Uiso 1 calc . .
C31 C 0.49780(19) 0.74221(15) 0.4680(4) 0.0584(9) Uani 1 d . .
H31A H 0.4948 0.7745 0.4006 0.07 Uiso 1 calc . .
H31B H 0.511 0.7063 0.4168 0.07 Uiso 1 calc . .
C32 C 0.6462(3) 0.89102(17) 1.3434(5) 0.0790(11) Uani 1 d . .
H32 H 0.6743 0.8849 1.4254 0.095 Uiso 1 calc . .
C33 C 0.6828(2) 0.90059(17) 1.2170(4) 0.0743(11) Uani 1 d . .
H33 H 0.736 0.9014 1.2154 0.089 Uiso 1 calc . .
C34 C 0.64284(18) 0.90897(14) 1.0922(4) 0.0540(8) Uani 1 d . .
C35 C 0.68372(19) 0.91932(17) 0.9561(4) 0.0681(10) Uani 1 d . .
H35A H 0.6518 0.905 0.8796 0.082 Uiso 1 calc . .
H35B H 0.6906 0.9618 0.9432 0.082 Uiso 1 calc . .
C36 C 0.75215(19) 0.82783(17) 0.9499(4) 0.0690(10) Uani 1 d . .
H36A H 0.7315 0.8152 1.0397 0.083 Uiso 1 calc . .
H36B H 0.8035 0.8117 0.9422 0.083 Uiso 1 calc . .
C37 C 0.70490(19) 0.80326(17) 0.8376(4) 0.0657(10) Uani 1 d . .
C38 C 0.6613(2) 0.78658(16) 0.7503(4) 0.0648(9) Uani 1 d . .
C39 C 0.6072(2) 0.76891(16) 0.6507(4) 0.0622(9) Uani 1 d . .
C40 C 0.5589(2) 0.75523(15) 0.5696(4) 0.0618(9) Uani 1 d . .
C41 C 0.3486(2) 0.83917(17) 0.4092(4) 0.0665(10) Uani 1 d . .
H41 H 0.3403 0.8031 0.3635 0.08 Uiso 1 calc . .
C42 C 0.3280(2) 0.8910(2) 0.3424(4) 0.0766(11) Uani 1 d . .
H42 H 0.3061 0.8903 0.2531 0.092 Uiso 1 calc . .
C43 C 0.3406(2) 0.9438(2) 0.4103(5) 0.0820(12) Uani 1 d . .
H43 H 0.3275 0.9793 0.3659 0.098 Uiso 1 calc . .
C44 C 0.3723(2) 0.94557(16) 0.5437(5) 0.0748(11) Uani 1 d . .
H44 H 0.3804 0.9818 0.5886 0.09 Uiso 1 calc . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.422(4) . ?
O1 C7 1.428(3) . ?
O2 C13 1.376(4) . ?
O2 C14 1.424(3) . ?
O3 C15 1.417(3) . ?
O3 C16 1.375(4) . ?
O4 C1 1.424(4) . ?
O4 C22 1.423(4) . ?
O5 C25 1.378(4) . ?
O5 C26 1.432(4) . ?
O6 C27 1.420(4) . ?
O6 C28 1.377(4) . ?
O7 C30 1.429(4) . ?
O7 C31 1.420(4) . ?
O8 C35 1.421(4) . ?
O8 C36 1.425(4) . ?
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C1 C2 1.467(5) . ?
C2 C3 1.184(5) . ?
C3 C4 1.382(5) . ?
C4 C5 1.193(5) . ?
C5 C6 1.459(5) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C7 C8 1.498(4) . ?
C8 C9 1.373(4) . ?
C8 C13 1.398(4) . ?
C9 H9 0.93 . ?
C9 C10 1.381(5) . ?
C10 H10 0.93 . ?
C10 C11 1.374(5) . ?
C11 H11 0.93 . ?
C11 C12 1.381(5) . ?
C12 H12 0.93 . ?
C12 C13 1.373(4) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C14 C15 1.490(5) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 C17 1.378(4) . ?
C16 C21 1.401(4) . ?
C17 H17 0.93 . ?
C17 C18 1.384(5) . ?
C18 H18 0.93 . ?
C18 C19 1.359(5) . ?
C19 H19 0.93 . ?
C19 C20 1.368(5) . ?
C20 H20 0.93 . ?
C20 C21 1.385(5) . ?
C21 C22 1.501(5) . ?
C22 H22A 0.97 . ?
C22 H22B 0.97 . ?
C23 H23 0.93 . ?
C23 C24 1.366(5) . ?
C23 C32 1.381(5) . ?
C24 H24 0.93 . ?
C24 C25 1.388(5) . ?
C25 C34 1.385(4) . ?
C26 H26A 0.97 . ?
C26 H26B 0.97 . ?
C26 C27 1.480(5) . ?
C27 H27A 0.97 . ?
C27 H27B 0.97 . ?
C28 C29 1.384(4) . ?
C28 C44 1.383(5) . ?
C29 C30 1.501(4) . ?
C29 C41 1.389(5) . ?
C30 H30A 0.97 . ?
C30 H30B 0.97 . ?
C31 H31A 0.97 . ?
C31 H31B 0.97 . ?
C31 C40 1.467(5) . ?
C32 H32 0.93 . ?
C32 C33 1.381(5) . ?
C33 H33 0.93 . ?
C33 C34 1.387(5) . ?
C34 C35 1.499(5) . ?
C35 H35A 0.97 . ?
C35 H35B 0.97 . ?
C36 H36A 0.97 . ?
C36 H36B 0.97 . ?
C36 C37 1.457(5) . ?
C37 C38 1.185(5) . ?
C38 C39 1.393(5) . ?
C39 C40 1.181(5) . ?
C41 H41 0.93 . ?
C41 C42 1.375(5) . ?
C42 H42 0.93 . ?
C42 C43 1.369(6) . ?
C43 H43 0.93 . ?
C43 C44 1.383(6) . ?
C44 H44 0.93 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C7 114.6(2) . . ?
C13 O2 C14 117.4(2) . . ?
C16 O3 C15 117.8(2) . . ?
C22 O4 C1 113.2(2) . . ?
C25 O5 C26 118.3(3) . . ?
C28 O6 C27 118.3(3) . . ?
C31 O7 C30 115.0(2) . . ?
C35 O8 C36 113.4(3) . . ?
O4 C1 H1A 109 . . ?
O4 C1 H1B 109 . . ?
O4 C1 C2 113.0(3) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109 . . ?
C2 C1 H1B 109 . . ?
C3 C2 C1 173.1(4) . . ?
C2 C3 C4 177.5(4) . . ?
C5 C4 C3 177.4(4) . . ?
C4 C5 C6 177.0(4) . . ?
O1 C6 C5 113.7(3) . . ?
O1 C6 H6A 108.8 . . ?
O1 C6 H6B 108.8 . . ?
C5 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
O1 C7 H7A 108.6 . . ?
O1 C7 H7B 108.6 . . ?
O1 C7 C8 114.5(3) . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C9 C8 C7 122.6(3) . . ?
C9 C8 C13 117.8(3) . . ?
C13 C8 C7 119.6(3) . . ?
C8 C9 H9 118.7 . . ?
C8 C9 C10 122.6(3) . . ?
C10 C9 H9 118.7 . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.3(3) . . ?
C11 C10 H10 120.9 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 120 . . ?
O2 C13 C8 115.3(3) . . ?
C12 C13 O2 124.2(3) . . ?
C12 C13 C8 120.5(3) . . ?
O2 C14 H14A 109.8 . . ?
O2 C14 H14B 109.8 . . ?
O2 C14 C15 109.3(3) . . ?
H14A C14 H14B 108.3 . . ?
C15 C14 H14A 109.8 . . ?
C15 C14 H14B 109.8 . . ?
O3 C15 C14 108.3(3) . . ?
O3 C15 H15A 110 . . ?
O3 C15 H15B 110 . . ?
C14 C15 H15A 110 . . ?
C14 C15 H15B 110 . . ?
H15A C15 H15B 108.4 . . ?
O3 C16 C17 124.5(3) . . ?
O3 C16 C21 114.9(3) . . ?
C17 C16 C21 120.6(3) . . ?
C16 C17 H17 120 . . ?
C16 C17 C18 119.9(3) . . ?
C18 C17 H17 120 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(4) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.9(4) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 118.9 . . ?
C19 C20 C21 122.2(3) . . ?
C21 C20 H20 118.9 . . ?
C16 C21 C22 120.4(3) . . ?
C20 C21 C16 117.2(3) . . ?
C20 C21 C22 122.4(3) . . ?
O4 C22 C21 113.4(3) . . ?
O4 C22 H22A 108.9 . . ?
O4 C22 H22B 108.9 . . ?
C21 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C24 C23 H23 119.9 . . ?
C24 C23 C32 120.3(4) . . ?
C32 C23 H23 119.9 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.7(3) . . ?
C25 C24 H24 119.7 . . ?
O5 C25 C24 124.2(3) . . ?
O5 C25 C34 115.4(3) . . ?
C34 C25 C24 120.3(3) . . ?
O5 C26 H26A 110.1 . . ?
O5 C26 H26B 110.1 . . ?
O5 C26 C27 108.1(3) . . ?
H26A C26 H26B 108.4 . . ?
C27 C26 H26A 110.1 . . ?
C27 C26 H26B 110.1 . . ?
O6 C27 C26 108.6(3) . . ?
O6 C27 H27A 110 . . ?
O6 C27 H27B 110 . . ?
C26 C27 H27A 110 . . ?
C26 C27 H27B 110 . . ?
H27A C27 H27B 108.4 . . ?
O6 C28 C29 115.2(3) . . ?
O6 C28 C44 124.0(3) . . ?
C44 C28 C29 120.8(3) . . ?
C28 C29 C30 119.4(3) . . ?
C28 C29 C41 117.9(3) . . ?
C41 C29 C30 122.5(3) . . ?
O7 C30 C29 114.8(3) . . ?
O7 C30 H30A 108.6 . . ?
O7 C30 H30B 108.6 . . ?
C29 C30 H30A 108.6 . . ?
C29 C30 H30B 108.6 . . ?
H30A C30 H30B 107.5 . . ?
O7 C31 H31A 108.8 . . ?
O7 C31 H31B 108.8 . . ?
O7 C31 C40 113.7(3) . . ?
H31A C31 H31B 107.7 . . ?
C40 C31 H31A 108.8 . . ?
C40 C31 H31B 108.8 . . ?
C23 C32 H32 120.6 . . ?
C33 C32 C23 118.7(4) . . ?
C33 C32 H32 120.6 . . ?
C32 C33 H33 118.9 . . ?
C32 C33 C34 122.2(4) . . ?
C34 C33 H33 118.9 . . ?
C25 C34 C33 117.8(3) . . ?
C25 C34 C35 120.9(3) . . ?
C33 C34 C35 121.3(3) . . ?
O8 C35 C34 114.0(3) . . ?
O8 C35 H35A 108.7 . . ?
O8 C35 H35B 108.7 . . ?
C34 C35 H35A 108.7 . . ?
C34 C35 H35B 108.7 . . ?
H35A C35 H35B 107.6 . . ?
O8 C36 H36A 108.9 . . ?
O8 C36 H36B 108.9 . . ?
O8 C36 C37 113.4(3) . . ?
H36A C36 H36B 107.7 . . ?
C37 C36 H36A 108.9 . . ?
C37 C36 H36B 108.9 . . ?
C38 C37 C36 174.0(4) . . ?
C37 C38 C39 177.1(4) . . ?
C40 C39 C38 177.1(4) . . ?
C39 C40 C31 176.4(4) . . ?
C29 C41 H41 118.9 . . ?
C42 C41 C29 122.2(4) . . ?
C42 C41 H41 118.9 . . ?
C41 C42 H42 120.8 . . ?
C43 C42 C41 118.4(4) . . ?
C43 C42 H42 120.8 . . ?
C42 C43 H43 119.3 . . ?
C42 C43 C44 121.4(4) . . ?
C44 C43 H43 119.3 . . ?
C28 C44 H44 120.4 . . ?
C43 C44 C28 119.2(4) . . ?
C43 C44 H44 120.4 . . ?

_database_code_depnum_ccdc_archive 'CCDC 978362'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_5i_nm1174ra
_audit_creation_date             2014-02-17T21:37:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C28 H20 O6'
_chemical_formula_sum            'C28 H20 O6'
_chemical_formula_weight         452.44
#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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'

_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_cell_length_a                   11.383(3)
_cell_length_b                   11.543(3)
_cell_length_c                   17.587(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.626(13)
_cell_angle_gamma                90
_cell_volume                     2290.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7523
_exptl_absorpt_correction_T_min  0.5433
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.1098 before and 0.0781 after correction.
        The Ratio of minimum to maximum transmission is 0.7079.
        The λ/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             944
#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_number            18779
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.805
_diffrn_reflns_theta_max         25.095
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_ful 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.985
_reflns_number_total             4022
_reflns_number_gt                2955
_reflns_threshold_expression     'I > 2σ(I)'
#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.034
_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     307
_refine_ls_number_reflns         4022
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0555P)²+0.2197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1095
#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#
_refine_special_details          
;
 ?
;
#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
_atom_sites_solution_hydrogens   geom
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
H1A H 0.3204 -0.1407 -0.1747 0.068 Uiso 1 calc . .
H1B H 0.4194 -0.0451 -0.1611 0.068 Uiso 1 calc . .
H6A H 0.5035 -0.2803 0.2435 0.066 Uiso 1 calc . .
H6B H 0.5564 -0.1546 0.2486 0.066 Uiso 1 calc . .
H9 H 0.2605 -0.1621 0.3688 0.064 Uiso 1 calc . .
H10 H 0.0935 -0.1198 0.4245 0.079 Uiso 1 calc . .
H11 H 0.0014 0.057 0.4024 0.073 Uiso 1 calc . .
H12 H 0.0729 0.1909 0.3226 0.06 Uiso 1 calc . .
H14A H 0.1706 0.3203 0.2516 0.054 Uiso 1 calc . .
H14B H 0.0982 0.2323 0.1951 0.054 Uiso 1 calc . .
H16 H 0.2511 0.4749 0.1895 0.075 Uiso 1 calc . .
H17 H 0.3404 0.5542 0.0908 0.1 Uiso 1 calc . .
H18 H 0.3747 0.4405 -0.0119 0.1 Uiso 1 calc . .
H19 H 0.3195 0.2487 -0.0168 0.079 Uiso 1 calc . .
H21A H 0.1467 0.1071 0.1056 0.063 Uiso 1 calc . .
H21B H 0.2799 0.0721 0.1069 0.063 Uiso 1 calc . .
H23 H 0.0164 0.214 0.0327 0.064 Uiso 1 calc . .
H24 H -0.1543 0.257 -0.0483 0.072 Uiso 1 calc . .
H25 H -0.1834 0.1855 -0.1721 0.074 Uiso 1 calc . .
H28 H -0.0478 0.057 -0.2112 0.062 Uiso 1 calc . .
C1 C 0.35174(17) -0.07842(16) -0.14089(10) 0.0570(5) Uani 1 d . .
C2 C 0.38789(17) -0.12312(16) -0.06434(13) 0.0581(5) Uani 1 d . .
C3 C 0.41232(17) -0.14993(16) 0.00148(13) 0.0597(5) Uani 1 d . .
C4 C 0.43982(16) -0.17425(16) 0.07920(13) 0.0576(5) Uani 1 d . .
C5 C 0.46124(15) -0.18879(15) 0.14665(12) 0.0538(5) Uani 1 d . .
C6 C 0.48666(16) -0.19991(15) 0.23018(11) 0.0549(5) Uani 1 d . .
C7 C 0.37447(14) -0.04331(13) 0.27261(9) 0.0416(4) Uani 1 d . .
C8 C 0.26875(14) -0.01228(13) 0.30982(8) 0.0400(4) Uani 1 d . .
C9 C 0.22293(16) -0.09111(14) 0.35886(10) 0.0531(5) Uani 1 d . .
C10 C 0.12319(19) -0.06583(16) 0.39271(11) 0.0658(6) Uani 1 d . .
C11 C 0.06800(18) 0.03952(16) 0.37915(11) 0.0612(5) Uani 1 d . .
C12 C 0.11080(16) 0.11982(14) 0.33114(9) 0.0497(4) Uani 1 d . .
C13 C 0.21038(14) 0.09498(13) 0.29548(8) 0.0390(4) Uani 1 d . .
C14 C 0.17692(15) 0.26160(13) 0.21282(9) 0.0448(4) Uani 1 d . .
C15 C 0.23139(14) 0.31246(13) 0.14680(9) 0.0435(4) Uani 1 d . .
C16 C 0.26484(18) 0.42866(15) 0.14822(11) 0.0629(5) Uani 1 d . .
C17 C 0.3184(2) 0.4766(2) 0.08901(14) 0.0835(7) Uani 1 d . .
C18 C 0.3386(2) 0.4087(2) 0.02767(14) 0.0830(7) Uani 1 d . .
C19 C 0.30539(17) 0.29380(19) 0.02485(11) 0.0661(5) Uani 1 d . .
C20 C 0.25099(14) 0.24397(14) 0.08349(9) 0.0455(4) Uani 1 d . .
C21 C 0.21605(17) 0.11749(14) 0.07968(9) 0.0521(4) Uani 1 d . .
C22 C 0.08818(15) 0.10879(13) -0.04058(9) 0.0451(4) Uani 1 d . .
C23 C 0.00416(16) 0.18244(15) -0.01639(10) 0.0531(5) Uani 1 d . .
C24 C -0.09758(16) 0.20881(16) -0.06521(12) 0.0603(5) Uani 1 d . .
C25 C -0.11632(16) 0.16463(16) -0.13878(12) 0.0617(5) Uani 1 d . .
C26 C -0.03421(15) 0.08903(15) -0.16228(10) 0.0521(4) Uani 1 d . .
C27 C 0.06803(14) 0.06000(13) -0.11428(9) 0.0411(4) Uani 1 d . .
C28 C 0.14963(16) -0.02930(14) -0.13835(9) 0.0455(4) Uani 1 d . .
O1 O 0.26124(10) 0.00970(9) -0.13724(6) 0.0506(3) Uani 1 d . .
O2 O 0.38698(10) -0.16037(9) 0.26751(6) 0.0502(3) Uani 1 d . .
O3 O 0.25313(9) 0.16836(9) 0.24447(6) 0.0434(3) Uani 1 d . .
O4 O 0.19049(11) 0.07475(10) 0.00285(6) 0.0580(3) Uani 1 d . .
O5 O 0.44303(11) 0.02220(10) 0.24863(7) 0.0609(4) Uani 1 d . .
O6 O 0.11995(13) -0.12598(11) -0.15707(9) 0.0792(5) Uani 1 d . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C2 C1 1.449(3) . ?
C3 C2 1.195(3) . ?
C4 C3 1.390(3) . ?
C5 C4 1.191(3) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C6 C5 1.465(3) . ?
C8 C7 1.488(2) . ?
C9 H9 0.93 . ?
C9 C8 1.401(2) . ?
C10 H10 0.93 . ?
C10 C9 1.381(2) . ?
C10 C11 1.375(3) . ?
C11 H11 0.93 . ?
C11 C12 1.385(2) . ?
C12 H12 0.93 . ?
C12 C13 1.396(2) . ?
C13 C8 1.412(2) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C14 C15 1.506(2) . ?
C15 C16 1.394(2) . ?
C15 C20 1.407(2) . ?
C16 H16 0.93 . ?
C17 H17 0.93 . ?
C17 C16 1.389(3) . ?
C18 H18 0.93 . ?
C18 C17 1.377(3) . ?
C19 H19 0.93 . ?
C19 C18 1.378(3) . ?
C20 C19 1.395(2) . ?
C20 C21 1.512(2) . ?
C21 H21A 0.97 . ?
C21 H21B 0.97 . ?
C22 C23 1.388(2) . ?
C22 C27 1.404(2) . ?
C23 H23 0.93 . ?
C23 C24 1.381(3) . ?
C24 H24 0.93 . ?
C24 C25 1.381(3) . ?
C25 H25 0.93 . ?
C25 C26 1.381(2) . ?
C26 H28 0.93 . ?
C27 C26 1.385(2) . ?
C28 C27 1.486(2) . ?
O1 C1 1.455(2) . ?
O1 C28 1.345(2) . ?
O2 C6 1.458(2) . ?
O2 C7 1.3629(18) . ?
O3 C13 1.3693(17) . ?
O3 C14 1.4465(18) . ?
O4 C21 1.4316(19) . ?
O4 C22 1.3631(19) . ?
O5 C7 1.2026(18) . ?
O6 C28 1.1993(19) . ?

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
H1A C1 H1B 108.3 . . ?
C2 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
C2 C1 O1 108.86(13) . . ?
O1 C1 H1A 109.9 . . ?
O1 C1 H1B 109.9 . . ?
C3 C2 C1 173.17(19) . . ?
C2 C3 C4 176.6(2) . . ?
C5 C4 C3 176.2(2) . . ?
C4 C5 C6 176.89(18) . . ?
H6A C6 H6B 108 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
O2 C6 H6A 109.4 . . ?
O2 C6 H6B 109.4 . . ?
O2 C6 C5 111.25(14) . . ?
O2 C7 C8 111.42(13) . . ?
O5 C7 C8 127.11(14) . . ?
O5 C7 O2 121.47(15) . . ?
C9 C8 C7 120.22(14) . . ?
C9 C8 C13 118.34(14) . . ?
C13 C8 C7 121.42(13) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C10 C9 C8 121.50(16) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C11 C10 C9 119.66(16) . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.53(17) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.57(16) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 119.39(14) . . ?
O3 C13 C8 117.37(13) . . ?
O3 C13 C12 123.20(14) . . ?
H14A C14 H14B 108.5 . . ?
C15 C14 H14A 110.2 . . ?
C15 C14 H14B 110.2 . . ?
O3 C14 H14A 110.2 . . ?
O3 C14 H14B 110.2 . . ?
O3 C14 C15 107.43(12) . . ?
C16 C15 C14 120.05(15) . . ?
C16 C15 C20 118.89(16) . . ?
C20 C15 C14 121.05(14) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C17 C16 C15 121.05(19) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C18 C17 C16 119.8(2) . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.1(2) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 121.1(2) . . ?
C20 C19 H19 119.5 . . ?
C15 C20 C21 120.59(14) . . ?
C19 C20 C15 119.06(17) . . ?
C19 C20 C21 120.33(16) . . ?
H21B C21 H21A 107.8 . . ?
C20 C21 H21A 108.9 . . ?
C20 C21 H21B 108.9 . . ?
O4 C21 H21A 108.9 . . ?
O4 C21 H21B 108.9 . . ?
O4 C21 C20 113.19(13) . . ?
C23 C22 C27 119.60(16) . . ?
O4 C22 C23 125.24(15) . . ?
O4 C22 C27 115.12(14) . . ?
C22 C23 H23 120 . . ?
C24 C23 H23 120 . . ?
C24 C23 C22 119.98(16) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C25 C24 C23 120.90(17) . . ?
C24 C25 H25 120.4 . . ?
C24 C25 C26 119.15(17) . . ?
C26 C25 H25 120.4 . . ?
C25 C26 H28 119.4 . . ?
C25 C26 C27 121.17(16) . . ?
C27 C26 H28 119.4 . . ?
C22 C27 C28 120.63(15) . . ?
C26 C27 C22 119.13(15) . . ?
C26 C27 C28 120.03(14) . . ?
O1 C28 C27 112.85(13) . . ?
O6 C28 C27 124.03(16) . . ?
O6 C28 O1 123.12(16) . . ?
C28 O1 C1 115.98(13) . . ?
C7 O2 C6 115.75(13) . . ?
C13 O3 C14 117.73(12) . . ?
C22 O4 C21 118.75(13) . . ?

_database_code_depnum_ccdc_archive 'CCDC 978447'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nm1097a2_06
_audit_creation_date             2014-02-17T20:07:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C28 H24 O4'
_chemical_formula_sum            'C28 H24 O4'
_chemical_formula_weight         424.47
#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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'

_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_cell_length_a                   8.867(3)
_cell_length_b                   16.757(5)
_cell_length_c                   14.800(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.210(7)
_cell_angle_gamma                90
_cell_volume                     2198.5(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3283
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.54
_cell_measurement_theta_min      2.43
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7523
_exptl_absorpt_correction_T_min  0.5923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.1098 before and 0.0781 after correction.
        The Ratio of minimum to maximum transmission is 0.7079.
        The λ/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_source                   'sealed tube'
_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_number            3845
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             3845
_reflns_number_gt                2940
_reflns_threshold_expression     >2sigma(I)
_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
;
#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0079(13)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3845
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0689P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1138
#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#
_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.
;
_atom_sites_solution_hydrogens   geom
#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
_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
H1A H 1.0363 -0.1484 0.3711 0.073 Uiso 1 1 calc R . .
H1B H 1.1337 -0.0952 0.3074 0.073 Uiso 1 1 calc R . .
H6A H 0.4108 0.1353 0.2964 0.076 Uiso 1 1 calc R . .
H6B H 0.3548 0.0783 0.2188 0.076 Uiso 1 1 calc R . .
H7 H 0.6401 0.039 0.0533 0.053 Uiso 1 1 calc R . .
H7A H 0.5536 0.2518 0.2591 0.064 Uiso 1 1 calc R . .
H7B H 0.6737 0.1949 0.2165 0.064 Uiso 1 1 calc R . .
H9 H 0.5184 0.3791 0.1942 0.063 Uiso 1 1 calc R . .
H10 H 0.5695 0.4739 0.0867 0.073 Uiso 1 1 calc R . .
H11 H 0.6935 0.4373 -0.0419 0.073 Uiso 1 1 calc R . .
H12 H 0.7629 0.3061 -0.0654 0.065 Uiso 1 1 calc R . .
H14A H 0.88 0.1813 -0.0448 0.066 Uiso 1 1 calc R . .
H14B H 0.7174 0.1749 -0.0884 0.066 Uiso 1 1 calc R . .
H16 H 0.9575 0.0681 -0.1325 0.061 Uiso 1 1 calc R . .
H17 H 0.9846 -0.0682 -0.1424 0.067 Uiso 1 1 calc R . .
H18 H 0.8404 -0.1515 -0.0558 0.062 Uiso 1 1 calc R . .
H20A H 0.566 -0.0866 0.1033 0.061 Uiso 1 1 calc R . .
H20B H 0.5738 -0.1542 0.0302 0.061 Uiso 1 1 calc R . .
H23 H 0.6639 -0.2581 -0.0135 0.068 Uiso 1 1 calc R . .
H24 H 0.7514 -0.3859 -0.0387 0.076 Uiso 1 1 calc R . .
H25 H 0.9148 -0.4463 0.0633 0.08 Uiso 1 1 calc R . .
H26 H 0.9866 -0.3796 0.1926 0.07 Uiso 1 1 calc R . .
H28A H 0.9383 -0.2778 0.3023 0.067 Uiso 1 1 calc R . .
H28B H 0.8225 -0.2094 0.2794 0.067 Uiso 1 1 calc R . .
C1 C 1.03898(18) -0.12376(10) 0.31184(11) 0.0612(4) Uani 1 1 d . . .
C2 C 0.91365(18) -0.06733(9) 0.30207(10) 0.0518(4) Uani 1 1 d . . .
C3 C 0.80632(17) -0.02594(9) 0.28705(10) 0.0485(4) Uani 1 1 d . . .
C4 C 0.68130(17) 0.02075(9) 0.26981(10) 0.0478(4) Uani 1 1 d . . .
C5 C 0.57128(18) 0.05983(9) 0.25543(10) 0.0521(4) Uani 1 1 d . . .
C6 C 0.43871(17) 0.11100(9) 0.23972(12) 0.0633(5) Uani 1 1 d . . .
C7 C 0.58211(17) 0.22491(9) 0.20401(10) 0.0534(4) Uani 1 1 d . . .
C8 C 0.60957(15) 0.28519(8) 0.13136(10) 0.0454(4) Uani 1 1 d . . .
C9 C 0.56811(17) 0.36412(9) 0.14215(11) 0.0526(4) Uani 1 1 d . . .
C10 C 0.59834(18) 0.42113(9) 0.07804(12) 0.0607(4) Uani 1 1 d . . .
C11 C 0.67165(19) 0.39900(9) 0.00129(11) 0.0609(4) Uani 1 1 d . . .
C12 C 0.71375(17) 0.32031(9) -0.01287(11) 0.0538(4) Uani 1 1 d . . .
C13 C 0.68223(15) 0.26305(8) 0.05166(10) 0.0455(4) Uani 1 1 d . . .
C14 C 0.78110(18) 0.15754(9) -0.03808(10) 0.0548(4) Uani 1 1 d . . .
C15 C 0.79476(15) 0.06781(8) -0.03948(9) 0.0450(4) Uani 1 1 d . . .
C16 C 0.89856(16) 0.03496(9) -0.09730(10) 0.0512(4) Uani 1 1 d . . .
C17 C 0.91506(18) -0.04665(9) -0.10307(10) 0.0559(4) Uani 1 1 d . . .
C18 C 0.82927(17) -0.09654(9) -0.05090(10) 0.0519(4) Uani 1 1 d . . .
C19 C 0.72592(14) -0.06508(9) 0.00911(9) 0.0419(3) Uani 1 1 d . . .
C20 C 0.70932(14) 0.01729(9) 0.01390(9) 0.0443(4) Uani 1 1 d . . .
C21 C 0.63428(16) -0.11888(9) 0.06820(11) 0.0505(4) Uani 1 1 d . . .
C22 C 0.77283(16) -0.24189(8) 0.10641(10) 0.0455(4) Uani 1 1 d . . .
C23 C 0.72872(17) -0.28224(9) 0.02843(11) 0.0563(4) Uani 1 1 d . . .
C24 C 0.78176(19) -0.35879(11) 0.01339(12) 0.0634(5) Uani 1 1 d . . .
C25 C 0.8785(2) -0.39520(10) 0.07428(13) 0.0665(5) Uani 1 1 d . . .
C26 C 0.92078(18) -0.35501(9) 0.15148(12) 0.0581(4) Uani 1 1 d . . .
C27 C 0.86837(16) -0.27879(8) 0.17027(10) 0.0460(4) Uani 1 1 d . . .
C28 C 0.90921(19) -0.23825(9) 0.25741(10) 0.0556(4) Uani 1 1 d . . .
O1 O 1.03130(11) -0.18401(6) 0.24433(7) 0.0536(3) Uani 1 1 d . . .
O2 O 0.46468(11) 0.17216(6) 0.17514(7) 0.0566(3) Uani 1 1 d . . .
O3 O 0.71820(12) 0.18362(6) 0.04441(7) 0.0543(3) Uani 1 1 d . . .
O4 O 0.72720(12) -0.16623(6) 0.12897(7) 0.0560(3) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.464(2) . ?
C2 C3 1.195(2) . ?
C3 C4 1.376(2) . ?
C4 C5 1.190(2) . ?
C5 C6 1.470(2) . ?
C7 C8 1.499(2) . ?
C8 C9 1.3829(19) . ?
C10 C9 1.377(2) . ?
C10 C11 1.372(2) . ?
C11 C12 1.387(2) . ?
C12 C13 1.386(2) . ?
C13 C8 1.4058(19) . ?
C14 C15 1.509(2) . ?
C15 C16 1.3840(19) . ?
C15 C20 1.3929(19) . ?
C17 C16 1.378(2) . ?
C18 C17 1.378(2) . ?
C19 C18 1.3932(19) . ?
C19 C21 1.5060(19) . ?
C20 C19 1.390(2) . ?
C22 C23 1.387(2) . ?
C22 C27 1.400(2) . ?
C23 C24 1.386(2) . ?
C24 C25 1.374(3) . ?
C25 C26 1.372(2) . ?
C27 C26 1.389(2) . ?
C27 C28 1.495(2) . ?
O1 C1 1.4211(18) . ?
O1 C28 1.4299(17) . ?
O2 C6 1.4233(17) . ?
O2 C7 1.4245(18) . ?
O3 C13 1.3735(17) . ?
O3 C14 1.4218(17) . ?
O4 C21 1.4443(18) . ?
O4 C22 1.3741(16) . ?

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
O1 C1 C2 111.37(13) . . ?
C3 C2 C1 173.42(16) . . ?
C2 C3 C4 179.14(16) . . ?
C5 C4 C3 178.62(16) . . ?
C4 C5 C6 177.50(18) . . ?
O2 C6 C5 112.72(12) . . ?
O2 C7 C8 109.38(12) . . ?
C9 C8 C7 120.94(13) . . ?
C9 C8 C13 118.49(13) . . ?
C13 C8 C7 120.55(13) . . ?
C10 C9 C8 121.87(14) . . ?
C11 C10 C9 119.05(15) . . ?
C10 C11 C12 121.05(15) . . ?
C13 C12 C11 119.66(14) . . ?
C12 C13 C8 119.86(14) . . ?
O3 C13 C8 115.63(12) . . ?
O3 C13 C12 124.51(13) . . ?
O3 C14 C15 110.56(11) . . ?
C16 C15 C14 117.36(12) . . ?
C16 C15 C20 119.05(14) . . ?
C20 C15 C14 123.58(12) . . ?
C17 C16 C15 120.39(13) . . ?
C18 C17 C16 120.44(13) . . ?
C17 C18 C19 120.40(14) . . ?
C18 C19 C21 120.92(13) . . ?
C20 C19 C18 118.69(12) . . ?
C20 C19 C21 120.39(12) . . ?
C19 C20 C15 121.01(12) . . ?
O4 C21 C19 112.51(12) . . ?
C23 C22 C27 120.17(14) . . ?
O4 C22 C23 124.95(14) . . ?
O4 C22 C27 114.87(13) . . ?
C24 C23 C22 119.63(16) . . ?
C25 C24 C23 120.99(16) . . ?
C26 C25 C24 118.95(16) . . ?
C25 C26 C27 122.11(16) . . ?
C22 C27 C28 120.91(13) . . ?
C26 C27 C22 118.11(15) . . ?
C26 C27 C28 120.96(14) . . ?
O1 C28 C27 110.02(11) . . ?
C1 O1 C28 112.43(11) . . ?
C6 O2 C7 111.90(12) . . ?
C13 O3 C14 117.44(11) . . ?
C22 O4 C21 121.50(12) . . ?

_database_code_depnum_ccdc_archive 'CCDC 970700'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nm1135a1_0m

_audit_creation_date             2014-03-06T15:44:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C24 H22 O4'
_chemical_formula_weight         374.41

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.903(4)
_cell_length_b                   23.110(10)
_cell_length_c                   10.380(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.380(10)
_cell_angle_gamma                90
_cell_volume                     2026.7(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0800 before and 0.0695 after correction.
        The Ratio of minimum to maximum transmission is 0.8557.
        The λ/2 correction factor is 0.0015.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_number            9134
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.762
_diffrn_reflns_theta_max         25.198
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_number_total             3649
_reflns_number_gt                2387
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0566P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0102(16)
_refine_ls_number_reflns         3649
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O -0.31031(14) 0.56711(5) 0.69232(13) 0.0574(4) Uani 1 d . .
O2 O -0.00970(15) 0.55703(6) 0.07259(13) 0.0638(4) Uani 1 d . .
O3 O 0.24876(14) 0.63747(6) 0.38574(12) 0.0579(4) Uani 1 d . .
O4 O 0.04345(14) 0.68432(5) 0.74587(12) 0.0561(4) Uani 1 d . .
C1 C -0.2895(2) 0.51031(8) 0.6492(2) 0.0605(5) Uani 1 d . .
H1A H -0.382 0.4873 0.6453 0.073 Uiso 1 calc . .
H1B H -0.1988 0.4927 0.7154 0.073 Uiso 1 calc . .
C2 C -0.2657(2) 0.50930(8) 0.5167(2) 0.0599(5) Uani 1 d . .
C3 C -0.2420(2) 0.51185(8) 0.4113(2) 0.0635(6) Uani 1 d . .
C4 C -0.2158(2) 0.51753(9) 0.2878(2) 0.0654(6) Uani 1 d . .
C5 C -0.1935(2) 0.52605(9) 0.1829(2) 0.0639(6) Uani 1 d . .
C6 C -0.1669(2) 0.53948(9) 0.0549(2) 0.0653(6) Uani 1 d . .
H6A H -0.1908 0.5056 -0.0031 0.078 Uiso 1 calc . .
H6B H -0.2387 0.5701 0.0095 0.078 Uiso 1 calc . .
C7 C 0.0304(2) 0.61099(8) 0.13900(19) 0.0565(5) Uani 1 d . .
H7A H 0.0148 0.6098 0.2273 0.068 Uiso 1 calc . .
H7B H -0.0359 0.6414 0.0857 0.068 Uiso 1 calc . .
C8 C 0.1998(2) 0.62251(7) 0.1545(2) 0.0514(5) Uani 1 d . .
C9 C 0.2525(3) 0.62029(9) 0.0440(2) 0.0677(6) Uani 1 d . .
H9 H 0.1807 0.6129 -0.0413 0.081 Uiso 1 calc . .
C10 C 0.4089(3) 0.62869(11) 0.0566(3) 0.0842(7) Uani 1 d . .
H10 H 0.4424 0.6274 -0.0196 0.101 Uiso 1 calc . .
C11 C 0.5153(3) 0.63901(10) 0.1816(3) 0.0789(7) Uani 1 d . .
H11 H 0.6216 0.6445 0.1905 0.095 Uiso 1 calc . .
C12 C 0.4660(2) 0.64133(9) 0.2937(2) 0.0650(6) Uani 1 d . .
H12 H 0.5391 0.6479 0.3788 0.078 Uiso 1 calc . .
C13 C 0.3093(2) 0.63398(7) 0.2810(2) 0.0498(5) Uani 1 d . .
C14 C 0.3539(2) 0.64752(8) 0.51959(18) 0.0586(5) Uani 1 d . .
H14A H 0.4228 0.6801 0.5199 0.07 Uiso 1 calc . .
H14B H 0.4189 0.6136 0.5528 0.07 Uiso 1 calc . .
C15 C 0.2537(2) 0.65996(8) 0.60533(18) 0.0546(5) Uani 1 d . .
H15 H 0.1826 0.6318 0.6134 0.066 Uiso 1 calc . .
C16 C 0.2597(2) 0.70842(8) 0.67023(19) 0.0581(5) Uani 1 d . .
H16 H 0.3363 0.7347 0.6642 0.07 Uiso 1 calc . .
C17 C 0.1600(2) 0.72666(8) 0.7521(2) 0.0608(5) Uani 1 d . .
H17A H 0.2253 0.7322 0.8457 0.073 Uiso 1 calc . .
H17B H 0.1095 0.7632 0.7183 0.073 Uiso 1 calc . .
C18 C -0.0717(2) 0.69779(8) 0.80154(18) 0.0503(5) Uani 1 d . .
C19 C -0.0743(2) 0.74747(9) 0.8739(2) 0.0629(6) Uani 1 d . .
H19 H 0.0056 0.7749 0.8871 0.076 Uiso 1 calc . .
C20 C -0.1961(3) 0.75613(10) 0.9264(2) 0.0728(6) Uani 1 d . .
H20 H -0.1972 0.7893 0.9769 0.087 Uiso 1 calc . .
C21 C -0.3155(3) 0.71674(10) 0.9053(2) 0.0707(6) Uani 1 d . .
H21 H -0.3986 0.7233 0.9397 0.085 Uiso 1 calc . .
C22 C -0.3121(2) 0.66704(9) 0.8325(2) 0.0592(5) Uani 1 d . .
H22 H -0.3938 0.6403 0.8177 0.071 Uiso 1 calc . .
C23 C -0.1898(2) 0.65648(8) 0.78177(17) 0.0489(5) Uani 1 d . .
C24 C -0.1750(2) 0.60170(8) 0.71032(19) 0.0536(5) Uani 1 d . .
H24A H -0.1633 0.6107 0.6227 0.064 Uiso 1 calc . .
H24B H -0.0815 0.5807 0.7632 0.064 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C24 1.409(2) . ?
O1 C1 1.418(2) . ?
O2 C6 1.413(2) . ?
O2 C7 1.415(2) . ?
O3 C13 1.360(2) . ?
O3 C14 1.428(2) . ?
O4 C18 1.362(2) . ?
O4 C17 1.413(2) . ?
C1 C2 1.456(3) . ?
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C2 C3 1.179(3) . ?
C3 C4 1.379(3) . ?
C4 C5 1.185(3) . ?
C5 C6 1.454(3) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.490(3) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.370(3) . ?
C8 C13 1.392(3) . ?
C9 C10 1.371(3) . ?
C9 H9 0.93 . ?
C10 C11 1.364(3) . ?
C10 H10 0.93 . ?
C11 C12 1.368(3) . ?
C11 H11 0.93 . ?
C12 C13 1.370(3) . ?
C12 H12 0.93 . ?
C14 C15 1.474(3) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 C16 1.299(3) . ?
C15 H15 0.93 . ?
C16 C17 1.471(3) . ?
C16 H16 0.93 . ?
C17 H17A 0.97 . ?
C17 H17B 0.97 . ?
C18 C19 1.376(3) . ?
C18 C23 1.387(2) . ?
C19 C20 1.373(3) . ?
C19 H19 0.93 . ?
C20 C21 1.364(3) . ?
C20 H20 0.93 . ?
C21 C22 1.380(3) . ?
C21 H21 0.93 . ?
C22 C23 1.373(3) . ?
C22 H22 0.93 . ?
C23 C24 1.494(3) . ?
C24 H24A 0.97 . ?
C24 H24B 0.97 . ?

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
C24 O1 C1 112.07(14) . . ?
C6 O2 C7 113.81(14) . . ?
C13 O3 C14 118.95(15) . . ?
C18 O4 C17 117.55(14) . . ?
O1 C1 C2 112.68(15) . . ?
O1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
O1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 C1 175.8(2) . . ?
C2 C3 C4 177.4(2) . . ?
C5 C4 C3 175.9(2) . . ?
C4 C5 C6 177.2(2) . . ?
O2 C6 C5 112.47(17) . . ?
O2 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
O2 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
O2 C7 C8 107.53(15) . . ?
O2 C7 H7A 110.2 . . ?
C8 C7 H7A 110.2 . . ?
O2 C7 H7B 110.2 . . ?
C8 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
C9 C8 C13 118.27(19) . . ?
C9 C8 C7 120.39(18) . . ?
C13 C8 C7 121.32(17) . . ?
C8 C9 C10 121.4(2) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
O3 C13 C12 124.34(18) . . ?
O3 C13 C8 115.44(17) . . ?
C12 C13 C8 120.21(19) . . ?
O3 C14 C15 106.44(15) . . ?
O3 C14 H14A 110.4 . . ?
C15 C14 H14A 110.4 . . ?
O3 C14 H14B 110.4 . . ?
C15 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
C16 C15 C14 123.17(18) . . ?
C16 C15 H15 118.4 . . ?
C14 C15 H15 118.4 . . ?
C15 C16 C17 127.78(18) . . ?
C15 C16 H16 116.1 . . ?
C17 C16 H16 116.1 . . ?
O4 C17 C16 110.07(15) . . ?
O4 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
O4 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.2 . . ?
O4 C18 C19 124.51(18) . . ?
O4 C18 C23 114.64(16) . . ?
C19 C18 C23 120.85(19) . . ?
C20 C19 C18 119.3(2) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C21 C20 C19 120.8(2) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.5(2) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C23 C22 C21 121.0(2) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C18 118.48(18) . . ?
C22 C23 C24 123.10(17) . . ?
C18 C23 C24 118.39(17) . . ?
O1 C24 C23 109.94(16) . . ?
O1 C24 H24A 109.7 . . ?
C23 C24 H24A 109.7 . . ?
O1 C24 H24B 109.7 . . ?
C23 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C24 O1 C1 C2 -63.3(2) . . . . ?
C7 O2 C6 C5 -67.6(2) . . . . ?
C6 O2 C7 C8 178.04(15) . . . . ?
O2 C7 C8 C9 53.2(2) . . . . ?
O2 C7 C8 C13 -124.79(17) . . . . ?
C13 C8 C9 C10 0.4(3) . . . . ?
C7 C8 C9 C10 -177.64(19) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C14 O3 C13 C12 -2.2(3) . . . . ?
C14 O3 C13 C8 178.27(16) . . . . ?
C11 C12 C13 O3 -177.72(18) . . . . ?
C11 C12 C13 C8 1.8(3) . . . . ?
C9 C8 C13 O3 177.96(16) . . . . ?
C7 C8 C13 O3 -4.0(2) . . . . ?
C9 C8 C13 C12 -1.6(3) . . . . ?
C7 C8 C13 C12 176.45(17) . . . . ?
C13 O3 C14 C15 169.65(15) . . . . ?
O3 C14 C15 C16 -119.63(19) . . . . ?
C14 C15 C16 C17 176.40(18) . . . . ?
C18 O4 C17 C16 -171.61(15) . . . . ?
C15 C16 C17 O4 -3.5(3) . . . . ?
C17 O4 C18 C19 -6.1(3) . . . . ?
C17 O4 C18 C23 174.71(15) . . . . ?
O4 C18 C19 C20 -179.43(17) . . . . ?
C23 C18 C19 C20 -0.3(3) . . . . ?
C18 C19 C20 C21 -1.3(3) . . . . ?
C19 C20 C21 C22 1.3(3) . . . . ?
C20 C21 C22 C23 0.4(3) . . . . ?
C21 C22 C23 C18 -2.0(3) . . . . ?
C21 C22 C23 C24 175.87(18) . . . . ?
O4 C18 C23 C22 -178.87(16) . . . . ?
C19 C18 C23 C22 1.9(3) . . . . ?
O4 C18 C23 C24 3.2(2) . . . . ?
C19 C18 C23 C24 -176.02(17) . . . . ?
C1 O1 C24 C23 -168.61(15) . . . . ?
C22 C23 C24 O1 5.9(3) . . . . ?
C18 C23 C24 O1 -176.23(15) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 970701'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nm1135a1_0m
_audit_creation_date             2014-02-20
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C24 H20 O4'
_chemical_formula_sum            'C24 H20 O4'
_chemical_formula_weight         372.42

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,y+1/2,-z+1/2
-x,-y,-z
x-1/2,-y-1/2,z-1/2

_cell_length_a                   4.856(3)
_cell_length_b                   53.09(4)
_cell_length_c                   7.510(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.902(18)
_cell_angle_gamma                90
_cell_volume                     1932(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.2805
_exptl_crystal_F_000             784.0

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7355
_exptl_absorpt_correction_T_min  0.5730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.1098 before and 0.0781 after correction.
        The Ratio of minimum to maximum transmission is 0.7079.
        The λ/2 correction factor is 0.0015.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_number            10743
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -61
_diffrn_reflns_limit_k_max       63
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         0.77
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_full        25.0259
_diffrn_measured_fraction_theta_full 0.9861
_diffrn_measured_fraction_theta_max 0.9861
_reflns_number_total             3345
_reflns_number_gt                1842
_reflns_threshold_expression     I>=2u(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    
;
        SHELXS, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_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.
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3345
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1366
_refine_ls_R_factor_gt           0.0797
_refine_ls_wR_factor_ref         0.2365
_refine_ls_goodness_of_fit_ref   1.1283
_refine_ls_restrained_S_all      1.1283
_refine_ls_shift/su_max          0.0159
_refine_ls_shift/su_mean         0.0034
_refine_diff_density_max         0.4804
_refine_diff_density_min         -0.3494
_refine_diff_density_rms         0.0933

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0 0 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.0033 0.0016 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
O 0.0106 0.006 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

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
H1a H 0.0816 0.0622 1.3139 0.089 Uiso 1
H1b H 0.0245 0.0693 1.1121 0.089 Uiso 1
H6a H 1.2598 0.1516 1.3421 0.084 Uiso 1
H6b H 1.1504 0.1616 1.1538 0.084 Uiso 1
H7a H 0.7386 0.2079 1.3106 0.078 Uiso 1
H7b H 0.6599 0.1833 1.2034 0.078 Uiso 1
H9 H 1.1808 0.2306 1.2133 0.077 Uiso 1
H10 H 1.3814 0.2475 0.9707 0.078 Uiso 1
H11 H 1.2689 0.2317 0.691 0.078 Uiso 1
H12 H 0.9444 0.1999 0.6501 0.072 Uiso 1
H14a H 0.7701 0.1607 0.6685 0.072 Uiso 1
H14b H 0.5218 0.1798 0.6475 0.072 Uiso 1
H17a H -0.0961 0.1121 0.7941 0.109 Uiso 1
H17b H -0.0028 0.1061 0.6026 0.109 Uiso 1
H19 H -0.2477 0.0754 0.5686 0.068 Uiso 1
H20 H -0.4333 0.0363 0.4979 0.086 Uiso 1
H21 H -0.2529 0.0006 0.6327 0.086 Uiso 1
H22 H 0.1109 0.0036 0.8382 0.078 Uiso 1
H24a H 0.5202 0.0294 0.959 0.078 Uiso 1
H24b H 0.492 0.0589 0.9602 0.078 Uiso 1
C1 C 0.1683(10) 0.06503(10) 1.2030(6) 0.0730(13) Uani 1
C2 C 0.3613(10) 0.08609(9) 1.2255(6) 0.0686(13) Uani 1
C3 C 0.5270(9) 0.10302(9) 1.2398(6) 0.0659(13) Uani 1
C4 C 0.7188(10) 0.12184(9) 1.2535(6) 0.0638(12) Uani 1
C5 C 0.8839(10) 0.13845(9) 1.2644(6) 0.0669(13) Uani 1
C6 C 1.0977(9) 0.15803(9) 1.2733(7) 0.0692(13) Uani 1
C7 C 0.8118(9) 0.19428(8) 1.2415(6) 0.0640(12) Uani 1
C8 C 0.9381(7) 0.20509(7) 1.0799(5) 0.0501(10) Uani 1
C9 C 1.1322(9) 0.22438(8) 1.0996(6) 0.0627(12) Uani 1
C10 C 1.2541(8) 0.23451(8) 0.9550(7) 0.0639(13) Uani 1
C11 C 1.1856(8) 0.22521(8) 0.7887(6) 0.0642(12) Uani 1
C12 C 0.9922(8) 0.20608(8) 0.7640(6) 0.0593(11) Uani 1
C13 C 0.8708(7) 0.19607(7) 0.9099(6) 0.0498(10) Uani 1
C14 C 0.6072(8) 0.16677(8) 0.7233(6) 0.0589(11) Uani 1
C15 C 0.4133(8) 0.14604(8) 0.7427(6) 0.0572(11) Uani 1
C16 C 0.2587(9) 0.12881(8) 0.7430(6) 0.0624(12) Uani 1
C17 C 0.0618(9) 0.10820(8) 0.7269(9) 0.0903(18) Uani 1
C18 C 0.0494(8) 0.06313(7) 0.7472(5) 0.0494(10) Uani 1
C19 C -0.1726(8) 0.06106(8) 0.6237(6) 0.0557(11) Uani 1
C20 C -0.2837(9) 0.03755(10) 0.5820(7) 0.0707(13) Uani 1
C21 C -0.1775(10) 0.01631(9) 0.6623(7) 0.0711(13) Uani 1
C22 C 0.0387(10) 0.01826(8) 0.7850(6) 0.0637(12) Uani 1
C23 C 0.1578(7) 0.04158(8) 0.8352(6) 0.0528(10) Uani 1
C24 C 0.3928(8) 0.04318(8) 0.9746(6) 0.0639(12) Uani 1
O1 O 0.2984(6) 0.04216(6) 1.1529(4) 0.0716(9) Uani 1
O2 O 1.0099(6) 0.18047(6) 1.3523(4) 0.0690(9) Uani 1
O3 O 0.6818(6) 0.17669(5) 0.8964(4) 0.0645(8) Uani 1
O4 O 0.1820(5) 0.08561(5) 0.7905(4) 0.0628(9) Uani 1



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.461(7) .
C1 O1 1.431(5) .
C2 C3 1.206(6) .
C3 C4 1.365(7) .
C4 C5 1.191(6) .
C5 C6 1.468(7) .
C6 O2 1.409(5) .
C7 C8 1.510(6) .
C7 O2 1.431(5) .
C8 C9 1.393(6) .
C8 C13 1.382(5) .
C9 C10 1.381(6) .
C10 C11 1.363(6) .
C11 C12 1.387(6) .
C12 C13 1.385(6) .
C13 O3 1.378(4) .
C14 C15 1.462(6) .
C14 O3 1.427(5) .
C15 C16 1.184(5) .
C16 C17 1.453(6) .
C17 O4 1.403(5) .
C18 C19 1.378(5) .
C18 C23 1.405(5) .
C18 O4 1.384(4) .
C19 C20 1.387(6) .
C20 C21 1.363(6) .
C21 C22 1.353(6) .
C22 C23 1.407(6) .
C23 C24 1.498(6) .
C24 O1 1.446(6) .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 C1 C2 112.9(4) . .
C3 C2 C1 177.5(5) . .
C4 C3 C2 178.6(5) . .
C5 C4 C3 179.2(5) . .
C6 C5 C4 176.9(5) . .
O2 C6 C5 112.6(4) . .
O2 C7 C8 111.6(3) . .
C9 C8 C7 120.2(4) . .
C13 C8 C7 121.9(4) . .
C13 C8 C9 118.0(4) . .
C10 C9 C8 121.7(4) . .
C11 C10 C9 119.2(4) . .
C12 C11 C10 120.6(4) . .
C13 C12 C11 119.7(4) . .
C12 C13 C8 120.8(4) . .
O3 C13 C8 116.1(4) . .
O3 C13 C12 123.1(4) . .
O3 C14 C15 108.2(3) . .
C16 C15 C14 174.2(5) . .
C17 C16 C15 174.9(5) . .
O4 C17 C16 111.0(3) . .
C23 C18 C19 120.2(4) . .
O4 C18 C19 123.8(3) . .
O4 C18 C23 116.0(3) . .
C20 C19 C18 119.9(4) . .
C21 C20 C19 121.0(4) . .
C22 C21 C20 119.4(4) . .
C23 C22 C21 122.4(4) . .
C22 C23 C18 117.2(4) . .
C24 C23 C18 121.7(4) . .
C24 C23 C22 121.1(4) . .
O1 C24 C23 111.8(3) . .
C24 O1 C1 112.7(3) . .
C7 O2 C6 113.5(3) . .
C14 O3 C13 118.0(3) . .
C18 O4 C17 118.7(3) . .

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 970702'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_5k

_audit_creation_date             2014-04-03T17:38:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C24 H24 O4'
_chemical_formula_weight         376.43

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   5.975(7)
_cell_length_b                   10.756(13)
_cell_length_c                   16.56(2)
_cell_angle_alpha                73.702(14)
_cell_angle_beta                 87.212(14)
_cell_angle_gamma                83.25(2)
_cell_volume                     1014(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      23.95

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_F_000             400
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.1098 before and 0.0781 after correction.
        The Ratio of minimum to maximum transmission is 0.7079.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.5283
_exptl_absorpt_correction_T_max  0.7463

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.1429
_diffrn_reflns_number            6191
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.984
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_ful 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.991
_reflns_number_total             3543
_reflns_number_gt                1834
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1646P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3543
_refine_ls_number_parameters     284
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.3118
_refine_ls_R_factor_gt           0.0821
_refine_ls_wR_factor_ref         0.2846
_refine_ls_wR_factor_gt          0.2199
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.108

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1A O 0.6665(19) 0.4366(8) 0.3619(6) 0.065(2) Uani 0.448(5) d A 1
O1B O 0.6007(16) 0.4871(7) 0.3481(5) 0.078(2) Uani 0.552(5) d A 2
O2 O 0.2388(5) 0.1354(2) 0.43454(14) 0.0759(8) Uani 1 d . .
O3 O 0.2285(5) -0.3002(2) 0.23982(12) 0.0755(9) Uani 1 d . .
O4 O 0.9475(5) 0.3067(2) 0.02079(13) 0.0848(10) Uani 1 d . .
C1 C 1.0048(8) 0.1833(4) 0.0782(2) 0.0814(12) Uani 1 d . .
H1A H 1.0217 0.1951 0.1334 0.098 Uiso 1 calc . .
H1B H 1.1498 0.1467 0.0613 0.098 Uiso 1 calc . .
C2 C 0.8427(9) 0.0905(4) 0.08457(19) 0.0790(12) Uani 1 d . .
C3 C 0.7075(8) 0.0150(4) 0.09526(19) 0.0754(11) Uani 1 d . .
C4 C 0.5608(8) -0.0759(4) 0.11242(19) 0.0763(12) Uani 1 d . .
C5 C 0.4356(8) -0.1574(4) 0.1318(2) 0.0801(12) Uani 1 d . .
C6 C 0.2954(9) -0.2625(4) 0.1542(2) 0.0917(14) Uani 1 d . .
H6A H 0.1613 -0.2368 0.1202 0.11 Uiso 1 calc . .
H6B H 0.3764 -0.3376 0.1403 0.11 Uiso 1 calc . .
C7 C 0.0445(8) -0.2230(4) 0.2635(3) 0.0918(15) Uani 1 d . .
H7A H -0.0506 -0.2798 0.3027 0.11 Uiso 1 calc . .
H7B H -0.0438 -0.179 0.2139 0.11 Uiso 1 calc . .
C8 C 0.1060(6) -0.1224(3) 0.30335(15) 0.0581(9) Uani 1 d . .
C9 C -0.0572(7) -0.0245(3) 0.30922(18) 0.0680(10) Uani 1 d . .
H9 H -0.1953 -0.0175 0.2838 0.082 Uiso 1 calc . .
C10 C -0.0202(7) 0.0636(3) 0.35213(18) 0.0687(11) Uani 1 d . .
H10 H -0.1326 0.1296 0.3555 0.082 Uiso 1 calc . .
C11 C 0.1814(6) 0.0540(3) 0.38972(15) 0.0573(9) Uani 1 d . .
C12 C 0.3492(6) -0.0428(4) 0.38377(18) 0.0704(11) Uani 1 d . .
H12 H 0.4876 -0.0493 0.4088 0.084 Uiso 1 calc . .
C13 C 0.3092(6) -0.1295(3) 0.34032(18) 0.0699(11) Uani 1 d . .
H13 H 0.4226 -0.1944 0.3359 0.084 Uiso 1 calc . .
C14A C 0.0654(8) 0.2307(3) 0.4485(2) 0.0762(12) Uani 0.448(5) d A 1
H14A H -0.0635 0.1917 0.4787 0.091 Uiso 0.448(5) calc A 1
H14B H 0.0169 0.2946 0.3966 0.091 Uiso 0.448(5) calc A 1
C14B C 0.0654(8) 0.2307(3) 0.4485(2) 0.0762(12) Uani 0.552(5) d A 2
H14C H -0.0467 0.1859 0.4865 0.091 Uiso 0.552(5) calc A 2
H14D H -0.0076 0.274 0.3954 0.091 Uiso 0.552(5) calc A 2
C15A C 0.2049(18) 0.2888(10) 0.5039(7) 0.067(3) Uani 0.448(5) d A 1
H15A H 0.1094 0.359 0.5184 0.081 Uiso 0.448(5) calc A 1
H15B H 0.2403 0.2216 0.5559 0.081 Uiso 0.448(5) calc A 1
C15B C 0.1389(17) 0.3321(8) 0.4838(5) 0.068(3) Uani 0.552(5) d A 2
H15C H 0.2235 0.2897 0.5345 0.081 Uiso 0.552(5) calc A 2
H15D H 0.0068 0.3826 0.4992 0.081 Uiso 0.552(5) calc A 2
C16A C 0.4218(15) 0.3406(7) 0.4662(4) 0.0666(16) Uani 0.448(5) d A 1
H16A H 0.5059 0.3565 0.5103 0.08 Uiso 0.448(5) calc A 1
H16B H 0.5114 0.274 0.4458 0.08 Uiso 0.448(5) calc A 1
C16B C 0.2842(14) 0.4236(8) 0.4222(6) 0.074(3) Uani 0.552(5) d A 2
H16C H 0.2286 0.4409 0.3656 0.089 Uiso 0.552(5) calc A 2
H16D H 0.2755 0.5058 0.4362 0.089 Uiso 0.552(5) calc A 2
C17A C 0.394(2) 0.4627(9) 0.3958(6) 0.070(3) Uani 0.448(5) d A 1
H17A H 0.364 0.5408 0.4146 0.084 Uiso 0.448(5) calc A 1
H17B H 0.2827 0.4613 0.3553 0.084 Uiso 0.448(5) calc A 1
C17B C 0.5237(12) 0.3641(6) 0.4257(3) 0.0666(16) Uani 0.552(5) d A 2
H17C H 0.5429 0.2816 0.4118 0.08 Uiso 0.552(5) calc A 2
H17D H 0.595 0.3558 0.4786 0.08 Uiso 0.552(5) calc A 2
C18 C 0.6440(8) 0.4333(3) 0.27907(19) 0.0732(11) Uani 1 d . .
C19 C 0.8082(8) 0.4925(4) 0.2238(2) 0.0830(12) Uani 1 d . .
H19 H 0.8994 0.546 0.2393 0.1 Uiso 1 calc . .
C20 C 0.8327(8) 0.4705(4) 0.1465(2) 0.0851(13) Uani 1 d . .
H20 H 0.9408 0.5108 0.1091 0.102 Uiso 1 calc . .
C21 C 0.7024(7) 0.3903(3) 0.12217(17) 0.0653(10) Uani 1 d . .
C22 C 0.5460(7) 0.3307(3) 0.17847(17) 0.0698(11) Uani 1 d . .
H22 H 0.4574 0.2754 0.1635 0.084 Uiso 1 calc . .
C23 C 0.5173(7) 0.3514(3) 0.25766(18) 0.0739(11) Uani 1 d . .
H23 H 0.4119 0.3094 0.2956 0.089 Uiso 1 calc . .
C24 C 0.7312(7) 0.3677(4) 0.03627(18) 0.0822(13) Uani 1 d . .
H24A H 0.6176 0.314 0.0298 0.099 Uiso 1 calc . .
H24B H 0.7047 0.4509 -0.0059 0.099 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1A C18 1.395(10) . ?
O1A C17A 1.716(16) . ?
O1B C18 1.420(8) . ?
O1B C17B 1.657(11) . ?
O2 C11 1.376(4) . ?
O2 C14A 1.427(4) . ?
O3 C7 1.406(4) . ?
O3 C6 1.412(5) . ?
O4 C1 1.414(4) . ?
O4 C24 1.424(5) . ?
C1 C2 1.450(7) . ?
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C2 C3 1.184(6) . ?
C3 C4 1.352(7) . ?
C4 C5 1.185(6) . ?
C5 C6 1.441(7) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.504(5) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.370(4) . ?
C8 C13 1.371(5) . ?
C9 C10 1.376(5) . ?
C9 H9 0.93 . ?
C10 C11 1.362(5) . ?
C10 H10 0.93 . ?
C11 C12 1.379(4) . ?
C12 C13 1.375(5) . ?
C12 H12 0.93 . ?
C13 H13 0.93 . ?
C14A C15A 1.564(12) . ?
C14A H14A 0.97 . ?
C14A H14B 0.97 . ?
C15A C16A 1.509(12) . ?
C15A H15A 0.97 . ?
C15A H15B 0.97 . ?
C15B C16B 1.522(10) . ?
C15B H15C 0.97 . ?
C15B H15D 0.97 . ?
C16A C17A 1.489(11) . ?
C16A H16A 0.97 . ?
C16A H16B 0.97 . ?
C16B C17B 1.494(10) . ?
C16B H16C 0.97 . ?
C16B H16D 0.97 . ?
C17A H17A 0.97 . ?
C17A H17B 0.97 . ?
C17B H17C 0.97 . ?
C17B H17D 0.97 . ?
C18 C23 1.354(6) . ?
C18 C19 1.392(6) . ?
C19 C20 1.363(5) . ?
C19 H19 0.93 . ?
C20 C21 1.377(6) . ?
C20 H20 0.93 . ?
C21 C22 1.369(5) . ?
C21 C24 1.508(4) . ?
C22 C23 1.390(4) . ?
C22 H22 0.93 . ?
C23 H23 0.93 . ?
C24 H24A 0.97 . ?
C24 H24B 0.97 . ?

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
C18 O1A C17A 103.7(7) . . ?
C18 O1B C17B 104.1(5) . . ?
C11 O2 C14A 116.8(3) . . ?
C7 O3 C6 116.1(3) . . ?
C1 O4 C24 114.0(3) . . ?
O4 C1 C2 114.7(4) . . ?
O4 C1 H1A 108.6 . . ?
C2 C1 H1A 108.6 . . ?
O4 C1 H1B 108.6 . . ?
C2 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C1 175.6(3) . . ?
C2 C3 C4 176.0(4) . . ?
C5 C4 C3 176.5(3) . . ?
C4 C5 C6 176.2(4) . . ?
O3 C6 C5 114.9(3) . . ?
O3 C6 H6A 108.5 . . ?
C5 C6 H6A 108.5 . . ?
O3 C6 H6B 108.5 . . ?
C5 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
O3 C7 C8 115.0(4) . . ?
O3 C7 H7A 108.5 . . ?
C8 C7 H7A 108.5 . . ?
O3 C7 H7B 108.5 . . ?
C8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C13 118.3(3) . . ?
C9 C8 C7 117.8(3) . . ?
C13 C8 C7 123.6(3) . . ?
C8 C9 C10 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120 . . ?
C9 C10 H10 120 . . ?
C10 C11 O2 125.5(3) . . ?
C10 C11 C12 120.0(3) . . ?
O2 C11 C12 114.4(3) . . ?
C13 C12 C11 119.2(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C8 C13 C12 121.5(3) . . ?
C8 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
O2 C14A C15A 97.2(5) . . ?
O2 C14A H14A 112.3 . . ?
C15A C14A H14A 112.3 . . ?
O2 C14A H14B 112.3 . . ?
C15A C14A H14B 112.3 . . ?
H14A C14A H14B 109.9 . . ?
C16A C15A C14A 117.0(8) . . ?
C16A C15A H15A 108 . . ?
C14A C15A H15A 108 . . ?
C16A C15A H15B 108 . . ?
C14A C15A H15B 108 . . ?
H15A C15A H15B 107.3 . . ?
C16B C15B H15C 109.1 . . ?
C16B C15B H15D 109.1 . . ?
H15C C15B H15D 107.8 . . ?
C17A C16A C15A 115.0(9) . . ?
C17A C16A H16A 108.5 . . ?
C15A C16A H16A 108.5 . . ?
C17A C16A H16B 108.5 . . ?
C15A C16A H16B 108.5 . . ?
H16A C16A H16B 107.5 . . ?
C17B C16B C15B 110.2(7) . . ?
C17B C16B H16C 109.6 . . ?
C15B C16B H16C 109.6 . . ?
C17B C16B H16D 109.6 . . ?
C15B C16B H16D 109.6 . . ?
H16C C16B H16D 108.1 . . ?
C16A C17A O1A 91.5(7) . . ?
C16A C17A H17A 113.4 . . ?
O1A C17A H17A 113.4 . . ?
C16A C17A H17B 113.4 . . ?
O1A C17A H17B 113.4 . . ?
H17A C17A H17B 110.7 . . ?
C16B C17B O1B 92.1(5) . . ?
C16B C17B H17C 113.3 . . ?
O1B C17B H17C 113.3 . . ?
C16B C17B H17D 113.3 . . ?
O1B C17B H17D 113.3 . . ?
H17C C17B H17D 110.6 . . ?
C23 C18 C19 120.5(3) . . ?
C23 C18 O1A 123.1(6) . . ?
C19 C18 O1A 114.1(6) . . ?
C23 C18 O1B 125.7(5) . . ?
C19 C18 O1B 112.7(5) . . ?
C20 C19 C18 118.8(4) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C19 C20 C21 122.0(4) . . ?
C19 C20 H20 119 . . ?
C21 C20 H20 119 . . ?
C22 C21 C20 118.1(3) . . ?
C22 C21 C24 120.7(4) . . ?
C20 C21 C24 121.2(4) . . ?
C21 C22 C23 121.1(4) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C18 C23 C22 119.4(4) . . ?
C18 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
O4 C24 C21 114.3(3) . . ?
O4 C24 H24A 108.7 . . ?
C21 C24 H24A 108.7 . . ?
O4 C24 H24B 108.7 . . ?
C21 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 970703'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nm679a
_audit_creation_date             2013-07-02T12:33:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H24 O5'
_chemical_formula_sum            'C24 H24 O5'
_chemical_formula_weight         392.43
#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
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                   20.0985(11)
_cell_length_b                   8.3800(4)
_cell_length_c                   12.1731(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.639(2)
_cell_angle_gamma                90
_cell_volume                     2049.42(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2313
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.29
_cell_measurement_theta_min      2.63
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0754 before and 0.0645 after correction.
        The Ratio of minimum to maximum transmission is 0.8773.
        The λ/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_number            7127
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         24.87
_diffrn_reflns_theta_full        24.87
_diffrn_measured_fraction_theta_full 0.855
_diffrn_measured_fraction_theta_max 0.855
_reflns_number_total             3040
_reflns_number_gt                2200
_reflns_threshold_expression     >2sigma(I)
#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.273
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.08
_refine_ls_extinction_coef       0.010(8)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.575
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3040
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.1097
_refine_ls_restrained_S_all      1.575
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3576
_refine_ls_wR_factor_ref         0.3896
#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#
_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.
;
_atom_sites_solution_hydrogens   geom
#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
_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
H10 H 0.5424 0.5556 -0.4413 0.11 Uiso 1 1 calc R . .
H15A H 0.6022 0.4647 0.1852 0.134 Uiso 1 1 calc R . .
H15B H 0.6307 0.2937 0.1679 0.134 Uiso 1 1 calc R . .
H14A H 0.6064 0.2925 -0.0061 0.144 Uiso 1 1 calc R . .
H14B H 0.5468 0.3889 0.0406 0.144 Uiso 1 1 calc R . .
H9 H 0.6326 0.6981 -0.3663 0.087 Uiso 1 1 calc R . .
H17A H 0.7468 0.2021 0.2148 0.101 Uiso 1 1 calc R . .
H17B H 0.8067 0.1859 0.1351 0.101 Uiso 1 1 calc R . .
H16A H 0.781 0.4492 0.0723 0.126 Uiso 1 1 calc R . .
H16B H 0.7293 0.3182 0.036 0.126 Uiso 1 1 calc R . .
H19 H 0.8269 0.0417 0.3058 0.083 Uiso 1 1 calc R . .
H20 H 0.8844 -0.0674 0.4551 0.099 Uiso 1 1 calc R . .
H21 H 0.9468 0.0903 0.5685 0.092 Uiso 1 1 calc R . .
H22 H 0.9521 0.3605 0.539 0.073 Uiso 1 1 calc R . .
H24A H 0.862 0.5845 0.3467 0.059 Uiso 1 1 calc R . .
H24B H 0.9182 0.5979 0.4389 0.059 Uiso 1 1 calc R . .
H1A H 0.9965 0.7094 0.2018 0.072 Uiso 1 1 calc R . .
H1B H 0.9653 0.7796 0.3078 0.072 Uiso 1 1 calc R . .
H6A H 0.679 1.0399 -0.0332 0.088 Uiso 1 1 calc R . .
H6B H 0.7229 0.997 -0.1331 0.088 Uiso 1 1 calc R . .
H7A H 0.7095 0.6459 -0.1143 0.086 Uiso 1 1 calc R . .
H7B H 0.7096 0.7513 -0.2213 0.086 Uiso 1 1 calc R . .
H12 H 0.5155 0.3488 -0.1511 0.122 Uiso 1 1 calc R . .
H11 H 0.4853 0.3838 -0.3333 0.123 Uiso 1 1 calc R . .
C1 C 0.9580(2) 0.7048(5) 0.2479(4) 0.0602(13) Uani 1 1 d . . .
C2 C 0.8984(3) 0.7548(5) 0.1825(4) 0.0597(13) Uani 1 1 d . . .
C3 C 0.8496(3) 0.7947(5) 0.1314(3) 0.0555(13) Uani 1 1 d . . .
C4 C 0.7969(3) 0.8429(5) 0.0668(4) 0.0585(13) Uani 1 1 d . . .
C5 C 0.7532(3) 0.8902(5) 0.0062(4) 0.0627(14) Uani 1 1 d . . .
C6 C 0.7017(3) 0.9531(6) -0.0692(5) 0.0735(16) Uani 1 1 d . . .
C7 C 0.6820(3) 0.7107(7) -0.1635(4) 0.0716(15) Uani 1 1 d . . .
C8 C 0.6261(3) 0.6125(6) -0.2122(4) 0.0682(15) Uani 1 1 d . . .
C9 C 0.6086(3) 0.6294(6) -0.3224(4) 0.0729(16) Uani 1 1 d . . .
C10 C 0.5548(4) 0.5431(8) -0.3676(6) 0.092(2) Uani 1 1 d . . .
C11 C 0.5209(4) 0.4411(9) -0.3031(7) 0.102(2) Uani 1 1 d . . .
C12 C 0.5382(4) 0.4211(8) -0.1942(7) 0.102(2) Uani 1 1 d . . .
C13 C 0.5902(3) 0.5106(8) -0.1500(5) 0.091(2) Uani 1 1 d . . .
C14 C 0.5943(4) 0.3918(9) 0.0291(7) 0.120(3) Uani 1 1 d . . .
C15 C 0.6294(4) 0.4007(10) 0.1375(7) 0.112(3) Uani 1 1 d . . .
C16 C 0.7475(4) 0.3763(10) 0.0989(5) 0.105(2) Uani 1 1 d . . .
C17 C 0.7802(3) 0.2612(7) 0.1757(5) 0.0843(18) Uani 1 1 d . . .
C18 C 0.8545(2) 0.2698(5) 0.3340(3) 0.0515(12) Uani 1 1 d . . .
C19 C 0.8520(3) 0.1071(6) 0.3528(4) 0.0693(15) Uani 1 1 d . . .
C20 C 0.8867(3) 0.0417(6) 0.4419(5) 0.0822(18) Uani 1 1 d . . .
C21 C 0.9235(3) 0.1351(6) 0.5090(5) 0.0765(16) Uani 1 1 d . . .
C22 C 0.9272(2) 0.2968(6) 0.4906(4) 0.0610(13) Uani 1 1 d . . .
C23 C 0.8946(2) 0.3659(5) 0.4013(3) 0.0465(11) Uani 1 1 d . . .
C24 C 0.9037(2) 0.5392(5) 0.3739(3) 0.0489(11) Uani 1 1 d . . .
O1 O 0.82119(17) 0.3473(4) 0.2507(2) 0.0683(11) Uani 1 1 d . . .
O4 O 0.95277(16) 0.5493(3) 0.2916(2) 0.0547(10) Uani 1 1 d . . .
O5 O 0.65389(18) 0.8391(4) -0.1049(3) 0.0715(11) Uani 1 1 d . . .
O6 O 0.6070(3) 0.5106(6) -0.0383(4) 0.125(2) Uani 1 1 d . . .
O7 O 0.6971(4) 0.4645(8) 0.1449(5) 0.139(2) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.480(7) . ?
C1 O4 1.413(5) . ?
C2 C3 1.194(7) . ?
C3 C4 1.362(7) . ?
C4 C5 1.198(7) . ?
C5 C6 1.462(7) . ?
C6 O5 1.415(6) . ?
C7 O5 1.417(6) . ?
C8 C7 1.501(7) . ?
C8 C13 1.362(8) . ?
C9 C8 1.384(8) . ?
C10 C9 1.401(8) . ?
C10 C11 1.357(10) . ?
C12 C11 1.371(10) . ?
C13 C12 1.383(9) . ?
C13 O6 1.392(8) . ?
C15 C14 1.480(11) . ?
C17 C16 1.483(9) . ?
C18 C19 1.384(6) . ?
C18 C23 1.389(6) . ?
C18 O1 1.364(5) . ?
C19 C20 1.385(8) . ?
C20 C21 1.339(8) . ?
C21 C22 1.376(7) . ?
C23 C22 1.381(6) . ?
C23 C24 1.502(6) . ?
C24 O4 1.427(5) . ?
O1 C17 1.410(6) . ?
O6 C14 1.319(8) . ?
O7 C15 1.461(9) . ?
O7 C16 1.386(9) . ?

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
O4 C1 C2 113.3(4) . . ?
C3 C2 C1 178.8(5) . . ?
C2 C3 C4 175.8(5) . . ?
C5 C4 C3 176.1(5) . . ?
C4 C5 C6 177.6(5) . . ?
O5 C6 C5 114.3(4) . . ?
O5 C7 C8 108.1(4) . . ?
C9 C8 C7 119.5(5) . . ?
C13 C8 C7 121.8(5) . . ?
C13 C8 C9 118.6(5) . . ?
C8 C9 C10 120.0(6) . . ?
C11 C10 C9 119.5(6) . . ?
C10 C11 C12 121.3(6) . . ?
C11 C12 C13 118.6(7) . . ?
C8 C13 C12 122.0(6) . . ?
C8 C13 O6 115.2(5) . . ?
C12 C13 O6 122.7(6) . . ?
O6 C14 C15 114.9(7) . . ?
O7 C15 C14 119.4(7) . . ?
O7 C16 C17 114.1(6) . . ?
O1 C17 C16 108.4(5) . . ?
C19 C18 C23 119.8(4) . . ?
O1 C18 C19 124.9(4) . . ?
O1 C18 C23 115.3(3) . . ?
C18 C19 C20 120.0(4) . . ?
C21 C20 C19 120.2(4) . . ?
C20 C21 C22 120.5(5) . . ?
C21 C22 C23 121.0(5) . . ?
C18 C23 C24 120.1(3) . . ?
C22 C23 C18 118.4(4) . . ?
C22 C23 C24 121.5(4) . . ?
O4 C24 C23 107.7(3) . . ?
C18 O1 C17 120.2(4) . . ?
C1 O4 C24 112.3(3) . . ?
C6 O5 C7 113.0(4) . . ?
C14 O6 C13 124.2(6) . . ?
C16 O7 C15 118.1(7) . . ?

_database_code_depnum_ccdc_archive 'CCDC 970704'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_6c

_audit_creation_date             2014-04-03T17:38:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C26 H28 O6'
_chemical_formula_weight         436.48

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
_space_group_IT_number           60
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'
_cell_length_a                   18.8390(8)
_cell_length_b                   13.5066(6)
_cell_length_c                   9.0088(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2292.30(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      21.38

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             928
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0970 before and 0.0839 after correction.
        The Ratio of minimum to maximum transmission is 0.8137.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6072
_exptl_absorpt_correction_T_max  0.7462

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.069
_diffrn_reflns_number            9702
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.855
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_ful 0.978
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_number_total             2031
_reflns_number_gt                1357
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0806P)²+0.6957P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2031
_refine_ls_number_parameters     158
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.085
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.177
_refine_ls_wR_factor_gt          0.1564
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.149
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.31027(9) 0.78441(13) 0.48854(18) 0.0605(5) Uani 1 d . .
O2 O 0.28320(9) 0.92408(13) 0.2234(2) 0.0617(5) Uani 1 d . .
O3A O 0.4100(7) 1.0513(17) 0.213(2) 0.098(4) Uani 0.663(15) d A 1
O3B O 0.4014(14) 1.071(4) 0.208(4) 0.098(4) Uani 0.337(15) d A 2
C1 C 0.37143(14) 0.7241(2) 0.5050(3) 0.0678(8) Uani 1 d . .
H1A H 0.3568 0.6553 0.5051 0.081 Uiso 1 calc . .
H1B H 0.3929 0.738 0.6006 0.081 Uiso 1 calc . .
C2 C 0.42547(15) 0.7382(2) 0.3881(3) 0.0605(7) Uani 1 d . .
C3 C 0.47240(15) 0.7429(2) 0.3007(3) 0.0590(7) Uani 1 d . .
C4 C 0.26356(15) 0.7510(2) 0.3745(3) 0.0619(7) Uani 1 d . .
H4A H 0.2441 0.6868 0.4003 0.074 Uiso 1 calc . .
H4B H 0.2891 0.7446 0.2815 0.074 Uiso 1 calc . .
C5 C 0.20505(13) 0.82539(19) 0.3588(3) 0.0531(6) Uani 1 d . .
C6 C 0.13927(15) 0.8097(2) 0.4204(3) 0.0712(8) Uani 1 d . .
H6 H 0.1311 0.7521 0.4743 0.085 Uiso 1 calc . .
C7 C 0.08500(16) 0.8778(3) 0.4038(4) 0.0815(10) Uani 1 d . .
H7 H 0.0409 0.8662 0.4469 0.098 Uiso 1 calc . .
C8 C 0.09650(15) 0.9619(3) 0.3241(4) 0.0750(9) Uani 1 d . .
H8 H 0.0599 1.0074 0.3122 0.09 Uiso 1 calc . .
C9 C 0.16171(14) 0.9801(2) 0.2609(3) 0.0595(7) Uani 1 d . .
H9 H 0.1691 1.0377 0.2063 0.071 Uiso 1 calc . .
C10 C 0.21626(12) 0.91246(19) 0.2789(3) 0.0492(6) Uani 1 d . .
C11 C 0.29652(14) 1.0046(2) 0.1255(3) 0.0602(7) Uani 1 d . .
H11A H 0.2813 1.0662 0.1708 0.072 Uiso 1 calc A 1
H11B H 0.2703 0.9956 0.0338 0.072 Uiso 1 calc A 1
C12A C 0.37383(15) 1.0081(3) 0.0941(3) 0.0723(8) Uani 0.663(15) d A 1
H12A H 0.3915 0.9415 0.0778 0.087 Uiso 0.663(15) calc A 1
H12B H 0.3823 1.0463 0.0047 0.087 Uiso 0.663(15) calc A 1
C12B C 0.37383(15) 1.0081(3) 0.0941(3) 0.0723(8) Uani 0.337(15) d A 2
H12C H 0.3947 0.9425 0.0996 0.087 Uiso 0.337(15) calc A 2
H12D H 0.383 1.0357 -0.0034 0.087 Uiso 0.337(15) calc A 2
C13A C 0.4828(3) 1.0377(10) 0.1843(5) 0.100(3) Uani 0.663(15) d A 1
H13A H 0.4903 0.9753 0.1333 0.12 Uiso 0.663(15) calc A 1
H13B H 0.5004 1.0908 0.1218 0.12 Uiso 0.663(15) calc A 1
C13B C 0.4705(4) 1.1057(10) 0.2068(11) 0.073(4) Uani 0.337(15) d A 2
H13C H 0.4883 1.079 0.1141 0.088 Uiso 0.337(15) calc A 2
H13D H 0.4637 1.1757 0.1878 0.088 Uiso 0.337(15) calc A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.419(3) . ?
O1 C4 1.426(3) . ?
O2 C10 1.366(3) . ?
O2 C11 1.422(3) . ?
O3A C12A 1.400(11) . ?
O3A C13A 1.407(14) . ?
O3B C13B 1.383(19) . ?
C1 C2 1.476(4) . ?
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C2 C3 1.186(3) . ?
C3 C3 1.385(5) 3_655 ?
C4 C5 1.498(4) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C5 C6 1.374(4) . ?
C5 C10 1.395(4) . ?
C6 C7 1.383(4) . ?
C6 H6 0.93 . ?
C7 C8 1.361(5) . ?
C7 H7 0.93 . ?
C8 C9 1.376(4) . ?
C8 H8 0.93 . ?
C9 C10 1.385(3) . ?
C9 H9 0.93 . ?
C11 C12A 1.484(4) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12A H12A 0.97 . ?
C12A H12B 0.97 . ?
C13A C13A 1.349(7) 3_655 ?
C13A H13A 0.97 . ?
C13A H13B 0.97 . ?
C13B C13B 1.358(9) 3_655 ?
C13B H13C 0.97 . ?
C13B H13D 0.97 . ?

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
C1 O1 C4 113.2(2) . . ?
C10 O2 C11 118.55(19) . . ?
C12A O3A C13A 106.1(9) . . ?
O1 C1 C2 114.3(2) . . ?
O1 C1 H1A 108.7 . . ?
C2 C1 H1A 108.7 . . ?
O1 C1 H1B 108.7 . . ?
C2 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C1 173.9(3) . . ?
C2 C3 C3 176.90(19) . 3_655 ?
O1 C4 C5 108.0(2) . . ?
O1 C4 H4A 110.1 . . ?
C5 C4 H4A 110.1 . . ?
O1 C4 H4B 110.1 . . ?
C5 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
C6 C5 C10 118.3(2) . . ?
C6 C5 C4 121.5(3) . . ?
C10 C5 C4 120.2(2) . . ?
C5 C6 C7 121.4(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 119.6(3) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 120.7(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C10 119.7(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
O2 C10 C9 124.5(2) . . ?
O2 C10 C5 115.2(2) . . ?
C9 C10 C5 120.3(2) . . ?
O2 C11 C12A 108.4(2) . . ?
O2 C11 H11A 110 . . ?
C12A C11 H11A 110 . . ?
O2 C11 H11B 110 . . ?
C12A C11 H11B 110 . . ?
H11A C11 H11B 108.4 . . ?
O3A C12A C11 110.2(6) . . ?
O3A C12A H12A 109.6 . . ?
C11 C12A H12A 109.6 . . ?
O3A C12A H12B 109.6 . . ?
C11 C12A H12B 109.6 . . ?
H12A C12A H12B 108.1 . . ?
C13A C13A O3A 107.8(9) 3_655 . ?
C13A C13A H13A 110.2 3_655 . ?
O3A C13A H13A 110.2 . . ?
C13A C13A H13B 110.2 3_655 . ?
O3A C13A H13B 110.2 . . ?
H13A C13A H13B 108.5 . . ?
C13B C13B O3B 140(2) 3_655 . ?
C13B C13B H13C 102.1 3_655 . ?
O3B C13B H13C 102.1 . . ?
C13B C13B H13D 102.1 3_655 . ?
O3B C13B H13D 102.1 . . ?
H13C C13B H13D 104.8 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 970705'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sci152_nm_1265_a1_0m

_audit_creation_date             2014-02-21T20:36:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C26 H24 O8'
_chemical_formula_sum            'C26 H24 O8'
_chemical_formula_weight         464.45

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.9306(5)
_cell_length_b                   13.0866(8)
_cell_length_c                   19.8566(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2320.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    2771
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      20.31

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             976
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0644 before and 0.0505 after correction.
        The Ratio of minimum to maximum transmission is 0.9221.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6876
_exptl_absorpt_correction_T_max  0.7457

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_number            12355
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.864
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.975
_reflns_number_total             4008
_reflns_number_gt                2895
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    
;
        SHELXS, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_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.
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0645P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4008
_refine_ls_number_parameters     323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.047
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.6906(3) 0.7627(2) -0.19078(13) 0.0541(7) Uani 1 d . .
O2 O 0.9296(3) 0.90527(19) 0.17616(12) 0.0488(6) Uani 1 d . .
O3 O 0.9254(3) 0.6355(2) -0.19755(12) 0.0560(7) Uani 1 d . .
O4 O 0.8568(3) 0.5221(3) -0.07602(13) 0.0712(9) Uani 1 d . .
O5 O 0.7834(3) 0.6129(2) 0.09273(13) 0.0704(9) Uani 1 d . .
O6 O 0.7923(3) 0.7435(2) 0.21304(12) 0.0565(8) Uani 1 d . .
O7 O 1.0835(3) 0.9799(2) 0.24856(13) 0.0671(8) Uani 1 d . .
O8 O 0.7491(4) 0.8976(3) -0.25254(19) 0.1000(12) Uani 1 d . .
C24 C 0.8377(5) 0.7594(4) -0.3557(2) 0.0739(13) Uani 1 d . .
H24 H 0.7851 0.8161 -0.3711 0.089 Uiso 1 calc . .
C25 C 0.8402(4) 0.7361(3) -0.28748(19) 0.0494(10) Uani 1 d . .
C26 C 0.7582(4) 0.8078(4) -0.2428(2) 0.0557(11) Uani 1 d . .
C1 C 0.6058(4) 0.8270(3) -0.1462(2) 0.0604(11) Uani 1 d . .
H1A H 0.5218 0.7888 -0.1281 0.073 Uiso 1 calc . .
H1B H 0.5663 0.8848 -0.1712 0.073 Uiso 1 calc . .
C2 C 0.6995(4) 0.8642(3) -0.0907(2) 0.0533(10) Uani 1 d . .
C3 C 0.7697(4) 0.8929(3) -0.0436(2) 0.0536(10) Uani 1 d . .
C4 C 0.8484(4) 0.9222(3) 0.01291(19) 0.0548(11) Uani 1 d . .
C5 C 0.9126(4) 0.9473(3) 0.0628(2) 0.0543(10) Uani 1 d . .
C6 C 0.9887(4) 0.9733(3) 0.12573(17) 0.0547(10) Uani 1 d . .
H6A H 1.096 0.9641 0.1212 0.066 Uiso 1 calc . .
H6B H 0.9691 1.0439 0.1379 0.066 Uiso 1 calc . .
C7 C 0.9892(4) 0.9174(3) 0.23731(18) 0.0454(9) Uani 1 d . .
C8 C 0.9284(4) 0.8469(3) 0.28938(17) 0.0452(9) Uani 1 d . .
C9 C 0.9727(5) 0.8682(3) 0.3548(2) 0.0628(12) Uani 1 d . .
H9 H 1.0366 0.9229 0.3629 0.075 Uiso 1 calc . .
C10 C 0.9235(6) 0.8095(4) 0.4080(2) 0.0831(15) Uani 1 d . .
H10 H 0.9527 0.8251 0.4518 0.1 Uiso 1 calc . .
C11 C 0.8295(6) 0.7266(4) 0.3957(2) 0.0732(13) Uani 1 d . .
H11 H 0.7964 0.6863 0.4313 0.088 Uiso 1 calc . .
C21 C 0.9977(5) 0.5920(3) -0.3113(2) 0.0652(11) Uani 1 d . .
H21 H 1.0525 0.5359 -0.2966 0.078 Uiso 1 calc . .
C20 C 0.9207(4) 0.6524(3) -0.26469(18) 0.0502(10) Uani 1 d . .
C19 C 1.0076(5) 0.5507(3) -0.1726(2) 0.0593(11) Uani 1 d . .
H19A H 1.1112 0.5555 -0.187 0.071 Uiso 1 calc . .
H19B H 0.966 0.4877 -0.1903 0.071 Uiso 1 calc . .
C17 C 0.8424(6) 0.5212(4) -0.0048(2) 0.0848(15) Uani 1 d . .
H17A H 0.9405 0.5113 0.0152 0.102 Uiso 1 calc . .
H17B H 0.78 0.4638 0.0084 0.102 Uiso 1 calc . .
C16 C 0.7769(5) 0.6154(4) 0.0218(2) 0.0736(14) Uani 1 d . .
H16A H 0.8319 0.674 0.005 0.088 Uiso 1 calc . .
H16B H 0.6737 0.6214 0.0071 0.088 Uiso 1 calc . .
C14 C 0.6909(4) 0.6620(3) 0.19921(18) 0.0468(9) Uani 1 d . .
H14A H 0.5975 0.6723 0.2232 0.056 Uiso 1 calc . .
H14B H 0.7337 0.5973 0.2134 0.056 Uiso 1 calc . .
C13 C 0.8327(4) 0.7628(3) 0.27746(18) 0.0448(9) Uani 1 d . .
C12 C 0.7857(5) 0.7042(3) 0.3311(2) 0.0558(11) Uani 1 d . .
H12 H 0.7232 0.6485 0.3234 0.067 Uiso 1 calc . .
C23 C 0.9145(7) 0.6970(4) -0.4011(2) 0.0890(17) Uani 1 d . .
H23 H 0.9122 0.7116 -0.4469 0.107 Uiso 1 calc . .
C22 C 0.9927(6) 0.6151(4) -0.3782(2) 0.0840(16) Uani 1 d . .
H22 H 1.0437 0.5739 -0.4087 0.101 Uiso 1 calc . .
C15 C 0.6641(4) 0.6616(4) 0.1251(2) 0.0560(11) Uani 1 d . .
C18 C 0.9996(5) 0.5506(4) -0.0983(2) 0.0634(12) Uani 1 d . .
H18A H 1.075(4) 0.497(3) -0.0808(19) 0.068(12) Uiso 1 d . .
H18B H 1.019(6) 0.617(5) -0.077(3) 0.13(2) Uiso 1 d . .
H15A H 0.658(4) 0.731(3) 0.110(2) 0.068(14) Uiso 1 d . .
H15B H 0.572(5) 0.627(3) 0.113(2) 0.095(17) Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C26 1.334(5) . ?
O1 C1 1.437(4) . ?
O2 C6 1.440(4) . ?
O2 C7 1.335(4) . ?
O3 C20 1.352(4) . ?
O3 C19 1.419(4) . ?
O4 C17 1.421(4) . ?
O4 C18 1.400(5) . ?
O5 C16 1.411(5) . ?
O5 C15 1.398(5) . ?
O6 C14 1.426(4) . ?
O6 C13 1.353(4) . ?
O7 C7 1.195(4) . ?
O8 C26 1.194(5) . ?
C24 H24 0.93 . ?
C24 C25 1.389(5) . ?
C24 C23 1.396(7) . ?
C25 C26 1.485(6) . ?
C25 C20 1.385(6) . ?
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C1 C2 1.468(5) . ?
C2 C3 1.187(5) . ?
C3 C4 1.378(5) . ?
C4 C5 1.191(5) . ?
C5 C6 1.462(5) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.488(5) . ?
C8 C9 1.386(5) . ?
C8 C13 1.414(5) . ?
C9 H9 0.93 . ?
C9 C10 1.378(6) . ?
C10 H10 0.93 . ?
C10 C11 1.393(6) . ?
C11 H11 0.93 . ?
C11 C12 1.373(5) . ?
C21 H21 0.93 . ?
C21 C20 1.398(5) . ?
C21 C22 1.362(6) . ?
C19 H19A 0.97 . ?
C19 H19B 0.97 . ?
C19 C18 1.477(6) . ?
C17 H17A 0.97 . ?
C17 H17B 0.97 . ?
C17 C16 1.462(6) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C14 C15 1.490(6) . ?
C13 C12 1.377(5) . ?
C12 H12 0.93 . ?
C23 H23 0.93 . ?
C23 C22 1.358(7) . ?
C22 H22 0.93 . ?
C15 H15A 0.96(4) . ?
C15 H15B 0.97(4) . ?
C18 H18A 1.03(4) . ?
C18 H18B 0.98(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 O1 C1 117.1(3) . . ?
C7 O2 C6 114.3(3) . . ?
C20 O3 C19 119.2(3) . . ?
C18 O4 C17 113.6(4) . . ?
C15 O5 C16 114.7(3) . . ?
C13 O6 C14 119.4(3) . . ?
C25 C24 H24 120.2 . . ?
C25 C24 C23 119.6(5) . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 115.9(4) . . ?
C20 C25 C24 120.0(4) . . ?
C20 C25 C26 124.1(4) . . ?
O1 C26 C25 114.0(4) . . ?
O8 C26 O1 122.1(4) . . ?
O8 C26 C25 123.9(4) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 C2 110.9(3) . . ?
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C3 C2 C1 176.7(4) . . ?
C2 C3 C4 177.2(5) . . ?
C5 C4 C3 178.1(4) . . ?
C4 C5 C6 177.1(4) . . ?
O2 C6 C5 106.2(3) . . ?
O2 C6 H6A 110.5 . . ?
O2 C6 H6B 110.5 . . ?
C5 C6 H6A 110.5 . . ?
C5 C6 H6B 110.5 . . ?
H6A C6 H6B 108.7 . . ?
O2 C7 C8 114.4(3) . . ?
O7 C7 O2 122.2(3) . . ?
O7 C7 C8 123.5(3) . . ?
C9 C8 C7 115.0(3) . . ?
C9 C8 C13 119.1(3) . . ?
C13 C8 C7 125.9(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.1(4) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.4(4) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(4) . . ?
C12 C11 H11 119.9 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C22 C21 C20 120.3(5) . . ?
O3 C20 C25 117.9(3) . . ?
O3 C20 C21 123.0(4) . . ?
C25 C20 C21 119.0(4) . . ?
O3 C19 H19A 109.9 . . ?
O3 C19 H19B 109.9 . . ?
O3 C19 C18 108.9(4) . . ?
H19A C19 H19B 108.3 . . ?
C18 C19 H19A 109.9 . . ?
C18 C19 H19B 109.9 . . ?
O4 C17 H17A 109 . . ?
O4 C17 H17B 109 . . ?
O4 C17 C16 112.8(4) . . ?
H17A C17 H17B 107.8 . . ?
C16 C17 H17A 109 . . ?
C16 C17 H17B 109 . . ?
O5 C16 C17 108.9(4) . . ?
O5 C16 H16A 109.9 . . ?
O5 C16 H16B 109.9 . . ?
C17 C16 H16A 109.9 . . ?
C17 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
O6 C14 H14A 110.3 . . ?
O6 C14 H14B 110.3 . . ?
O6 C14 C15 107.1(3) . . ?
H14A C14 H14B 108.5 . . ?
C15 C14 H14A 110.3 . . ?
C15 C14 H14B 110.3 . . ?
O6 C13 C8 117.7(3) . . ?
O6 C13 C12 123.1(3) . . ?
C12 C13 C8 119.2(3) . . ?
C11 C12 C13 121.1(4) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C24 C23 H23 120.1 . . ?
C22 C23 C24 119.8(5) . . ?
C22 C23 H23 120.1 . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.2(5) . . ?
C23 C22 H22 119.4 . . ?
O5 C15 C14 109.5(3) . . ?
O5 C15 H15A 109(2) . . ?
O5 C15 H15B 109(3) . . ?
C14 C15 H15A 108(2) . . ?
C14 C15 H15B 113(3) . . ?
H15A C15 H15B 108(4) . . ?
O4 C18 C19 111.2(4) . . ?
O4 C18 H18A 108(2) . . ?
O4 C18 H18B 105(3) . . ?
C19 C18 H18A 108(2) . . ?
C19 C18 H18B 115(3) . . ?
H18A C18 H18B 110(4) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 970706'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nm819a

_audit_creation_date             2013-04-10T18:48:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C30 H32 O4'
_chemical_formula_sum            'C30 H32 O4'
_chemical_formula_weight         456.56

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

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'
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
_cell_length_a                   15.205(6)
_cell_length_b                   16.280(7)
_cell_length_c                   10.936(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.697(9)
_cell_angle_gamma                90
_cell_volume                     2578.9(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    298

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.0677 before and 0.0538 after correction.
        The Ratio of minimum to maximum transmission is 0.8973.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6687
_exptl_absorpt_correction_T_max  0.7452

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_number            12584
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.41
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             4539
_reflns_number_gt                2536
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        2008). A64, 112-122
;
_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.
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0727P)²+0.1996P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0056(11)
_refine_ls_number_reflns         4539
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1578
_refine_ls_wR_factor_gt          0.1295
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O -0.07132(12) 0.43317(10) 0.14406(17) 0.0777(5) Uani 1 1 d . . .
O2 O 0.23174(11) 0.47023(10) 0.53586(15) 0.0710(5) Uani 1 1 d . . .
O3 O 0.37029(10) 0.27047(9) 0.51823(14) 0.0619(5) Uani 1 1 d . . .
O4 O -0.11955(11) 0.23861(9) -0.05966(16) 0.0661(5) Uani 1 1 d . . .
C1 C -0.2626(2) 0.46283(19) -0.2139(3) 0.0905(9) Uani 1 1 d . . .
H1 H -0.306 0.468 -0.2944 0.109 Uiso 1 1 calc R . .
C2 C -0.2406(2) 0.38622(17) -0.1576(3) 0.0821(8) Uani 1 1 d . . .
H2 H -0.2701 0.3401 -0.2015 0.098 Uiso 1 1 calc R . .
C3 C -0.17639(17) 0.37621(14) -0.0389(2) 0.0614(6) Uani 1 1 d . . .
C4 C -0.13350(16) 0.44625(14) 0.0252(2) 0.0612(6) Uani 1 1 d . . .
C5 C -0.01857(17) 0.50119(14) 0.2092(2) 0.0678(7) Uani 1 1 d . . .
H5A H -0.0592 0.5426 0.2262 0.081 Uiso 1 1 calc R . .
H5B H 0.0153 0.5257 0.1562 0.081 Uiso 1 1 calc R . .
C6 C 0.04757(16) 0.47137(14) 0.3333(2) 0.0660(7) Uani 1 1 d . . .
H6A H 0.0903 0.4323 0.3156 0.079 Uiso 1 1 calc R . .
H6B H 0.0137 0.4437 0.3835 0.079 Uiso 1 1 calc R . .
C7 C 0.10051(18) 0.54315(15) 0.4085(3) 0.0736(7) Uani 1 1 d . . .
H7A H 0.1396 0.5659 0.3614 0.088 Uiso 1 1 calc R . .
H7B H 0.0566 0.5854 0.4133 0.088 Uiso 1 1 calc R . .
C8 C 0.15936(18) 0.52385(16) 0.5416(3) 0.0767(8) Uani 1 1 d . . .
H8A H 0.1851 0.5741 0.5857 0.092 Uiso 1 1 calc R . .
H8B H 0.1223 0.4979 0.589 0.092 Uiso 1 1 calc R . .
C9 C 0.29612(17) 0.44902(14) 0.6493(2) 0.0606(6) Uani 1 1 d . . .
C10 C 0.36377(17) 0.39380(14) 0.6405(2) 0.0597(6) Uani 1 1 d . . .
C11 C 0.36485(16) 0.35836(13) 0.5129(2) 0.0572(6) Uani 1 1 d . . .
H11 H 0.3085 0.3749 0.4461 0.069 Uiso 1 1 calc R . .
C12 C 0.44809(19) 0.38595(16) 0.4753(2) 0.0748(8) Uani 1 1 d . . .
H12A H 0.4507 0.4455 0.477 0.09 Uiso 1 1 calc R . .
H12B H 0.5035 0.3657 0.5383 0.09 Uiso 1 1 calc R . .
C13 C 0.44720(19) 0.35697(19) 0.3457(3) 0.0816(8) Uani 1 1 d . . .
H13 H 0.4285 0.3031 0.3244 0.098 Uiso 1 1 calc R . .
C14 C 0.4695(2) 0.3987(2) 0.2613(3) 0.1157(12) Uani 1 1 d . . .
H14A H 0.4886 0.4529 0.2781 0.139 Uiso 1 1 calc R . .
H14B H 0.4666 0.3749 0.1828 0.139 Uiso 1 1 calc R . .
C15 C -0.3646(3) 0.2996(3) 0.1033(5) 0.1638(19) Uani 1 1 d . . .
H15A H -0.4073 0.2782 0.0303 0.197 Uiso 1 1 calc R . .
H15B H -0.3848 0.3283 0.1633 0.197 Uiso 1 1 calc R . .
C16 C -0.2806(3) 0.2899(2) 0.1208(4) 0.1128(12) Uani 1 1 d . . .
H16 H -0.2404 0.3123 0.1951 0.135 Uiso 1 1 calc R . .
C17 C -0.2392(2) 0.24609(17) 0.0342(3) 0.0947(10) Uani 1 1 d . . .
H17A H -0.2847 0.2408 -0.0496 0.114 Uiso 1 1 calc R . .
H17B H -0.2216 0.1912 0.0673 0.114 Uiso 1 1 calc R . .
C18 C -0.15330(18) 0.29139(14) 0.0204(2) 0.0660(7) Uani 1 1 d . . .
H18 H -0.1068 0.2962 0.1048 0.079 Uiso 1 1 calc R . .
C19 C 0.2968(2) 0.48003(16) 0.7676(3) 0.0759(8) Uani 1 1 d . . .
H19 H 0.2505 0.5159 0.773 0.091 Uiso 1 1 calc R . .
C20 C 0.3654(2) 0.45811(18) 0.8768(3) 0.0883(9) Uani 1 1 d . . .
H20 H 0.3657 0.4795 0.9558 0.106 Uiso 1 1 calc R . .
C21 C 0.4333(2) 0.4051(2) 0.8701(3) 0.0953(10) Uani 1 1 d . . .
H21 H 0.4801 0.3908 0.944 0.114 Uiso 1 1 calc R . .
C22 C 0.4318(2) 0.37295(16) 0.7523(3) 0.0796(8) Uani 1 1 d . . .
H22 H 0.4779 0.3364 0.7483 0.095 Uiso 1 1 calc R . .
C23 C 0.28615(17) 0.23230(15) 0.5143(2) 0.0699(7) Uani 1 1 d . . .
H23A H 0.2614 0.2585 0.5765 0.084 Uiso 1 1 calc R . .
H23B H 0.2978 0.1751 0.5388 0.084 Uiso 1 1 calc R . .
C24 C 0.21698(18) 0.23658(15) 0.3868(3) 0.0665(7) Uani 1 1 d . . .
C25 C 0.16117(18) 0.23936(15) 0.2835(3) 0.0665(7) Uani 1 1 d . . .
C26 C 0.09681(18) 0.24405(15) 0.1638(3) 0.0673(7) Uani 1 1 d . . .
C27 C 0.04050(18) 0.24969(15) 0.0601(3) 0.0685(7) Uani 1 1 d . . .
C28 C -0.03056(17) 0.25927(16) -0.0645(2) 0.0701(7) Uani 1 1 d . . .
H28A H -0.0308 0.3158 -0.0927 0.084 Uiso 1 1 calc R . .
H28B H -0.0152 0.2246 -0.1272 0.084 Uiso 1 1 calc R . .
C29 C -0.15528(19) 0.52324(15) -0.0303(3) 0.0724(7) Uani 1 1 d . . .
H29 H -0.1264 0.5698 0.013 0.087 Uiso 1 1 calc R . .
C30 C -0.2195(2) 0.53054(18) -0.1493(3) 0.0819(8) Uani 1 1 d . . .
H30 H -0.2338 0.5822 -0.1862 0.098 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.372(3) . ?
O1 C5 1.425(3) . ?
O2 C8 1.421(3) . ?
O2 C9 1.370(3) . ?
O3 C11 1.433(3) . ?
O3 C23 1.411(3) . ?
O4 C18 1.429(3) . ?
O4 C28 1.411(3) . ?
C1 H1 0.93 . ?
C1 C2 1.386(4) . ?
C1 C30 1.365(4) . ?
C2 H2 0.93 . ?
C2 C3 1.377(3) . ?
C3 C4 1.392(3) . ?
C3 C18 1.521(3) . ?
C4 C29 1.388(3) . ?
C5 H5A 0.97 . ?
C5 H5B 0.97 . ?
C5 C6 1.503(3) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C6 C7 1.513(3) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C7 C8 1.492(4) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 C10 1.391(3) . ?
C9 C19 1.386(3) . ?
C10 C11 1.515(3) . ?
C10 C22 1.383(3) . ?
C11 H11 0.98 . ?
C11 C12 1.513(3) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C12 C13 1.490(3) . ?
C13 H13 0.93 . ?
C13 C14 1.272(4) . ?
C14 H14A 0.93 . ?
C14 H14B 0.93 . ?
C15 H15A 0.93 . ?
C15 H15B 0.93 . ?
C15 C16 1.244(5) . ?
C16 H16 0.93 . ?
C16 C17 1.471(4) . ?
C17 H17A 0.97 . ?
C17 H17B 0.97 . ?
C17 C18 1.547(4) . ?
C18 H18 0.98 . ?
C19 H19 0.93 . ?
C19 C20 1.373(4) . ?
C20 H20 0.93 . ?
C20 C21 1.363(4) . ?
C21 H21 0.93 . ?
C21 C22 1.384(4) . ?
C22 H22 0.93 . ?
C23 H23A 0.97 . ?
C23 H23B 0.97 . ?
C23 C24 1.470(4) . ?
C24 C25 1.190(3) . ?
C25 C26 1.378(4) . ?
C26 C27 1.199(4) . ?
C27 C28 1.467(4) . ?
C28 H28A 0.97 . ?
C28 H28B 0.97 . ?
C29 H29 0.93 . ?
C29 C30 1.374(4) . ?
C30 H30 0.93 . ?

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 C5 118.29(18) . . ?
C9 O2 C8 117.69(19) . . ?
C23 O3 C11 113.43(17) . . ?
C28 O4 C18 114.00(18) . . ?
C2 C1 H1 120.5 . . ?
C30 C1 H1 120.5 . . ?
C30 C1 C2 119.0(3) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 C1 122.1(3) . . ?
C3 C2 H2 118.9 . . ?
C2 C3 C4 117.8(2) . . ?
C2 C3 C18 121.0(2) . . ?
C4 C3 C18 121.1(2) . . ?
O1 C4 C3 115.6(2) . . ?
O1 C4 C29 124.0(2) . . ?
C29 C4 C3 120.4(2) . . ?
O1 C5 H5A 109.9 . . ?
O1 C5 H5B 109.9 . . ?
O1 C5 C6 108.70(19) . . ?
H5A C5 H5B 108.3 . . ?
C6 C5 H5A 109.9 . . ?
C6 C5 H5B 109.9 . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
C5 C6 C7 109.9(2) . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
C6 C7 H7A 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C8 C7 C6 115.5(2) . . ?
C8 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
O2 C8 C7 109.2(2) . . ?
O2 C8 H8A 109.8 . . ?
O2 C8 H8B 109.8 . . ?
C7 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
O2 C9 C10 116.1(2) . . ?
O2 C9 C19 123.6(2) . . ?
C19 C9 C10 120.2(2) . . ?
C9 C10 C11 121.7(2) . . ?
C22 C10 C9 117.9(2) . . ?
C22 C10 C11 120.4(2) . . ?
O3 C11 C10 111.06(18) . . ?
O3 C11 H11 109.3 . . ?
O3 C11 C12 105.35(18) . . ?
C10 C11 H11 109.3 . . ?
C12 C11 C10 112.43(19) . . ?
C12 C11 H11 109.3 . . ?
C11 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 C11 113.5(2) . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C12 C13 H13 116.8 . . ?
C14 C13 C12 126.4(3) . . ?
C14 C13 H13 116.8 . . ?
C13 C14 H14A 120 . . ?
C13 C14 H14B 120 . . ?
H14A C14 H14B 120 . . ?
H15A C15 H15B 120 . . ?
C16 C15 H15A 120 . . ?
C16 C15 H15B 120 . . ?
C15 C16 H16 117.1 . . ?
C15 C16 C17 125.7(5) . . ?
C17 C16 H16 117.1 . . ?
C16 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C16 C17 C18 111.8(3) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
O4 C18 C3 111.37(19) . . ?
O4 C18 C17 104.1(2) . . ?
O4 C18 H18 109.6 . . ?
C3 C18 C17 112.5(2) . . ?
C3 C18 H18 109.6 . . ?
C17 C18 H18 109.6 . . ?
C9 C19 H19 119.8 . . ?
C20 C19 C9 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.3 . . ?
C20 C21 C22 119.4(3) . . ?
C22 C21 H21 120.3 . . ?
C10 C22 C21 121.7(3) . . ?
C10 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
O3 C23 H23A 109 . . ?
O3 C23 H23B 109 . . ?
O3 C23 C24 112.9(2) . . ?
H23A C23 H23B 107.8 . . ?
C24 C23 H23A 109 . . ?
C24 C23 H23B 109 . . ?
C25 C24 C23 179.4(3) . . ?
C24 C25 C26 179.0(3) . . ?
C27 C26 C25 178.7(3) . . ?
C26 C27 C28 177.5(3) . . ?
O4 C28 C27 112.6(2) . . ?
O4 C28 H28A 109.1 . . ?
O4 C28 H28B 109.1 . . ?
C27 C28 H28A 109.1 . . ?
C27 C28 H28B 109.1 . . ?
H28A C28 H28B 107.8 . . ?
C4 C29 H29 120 . . ?
C30 C29 C4 119.9(3) . . ?
C30 C29 H29 120 . . ?
C1 C30 C29 120.8(3) . . ?
C1 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 970707'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nm819a
_audit_creation_date             2013-04-10T18:48:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C30 H32 O5'
_chemical_formula_sum            'C30 H32 O5'
_chemical_formula_weight         472.56
#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.6914(9)
_cell_length_b                   12.4846(14)
_cell_length_c                   25.241(3)
_cell_angle_alpha                77.626(3)
_cell_angle_beta                 87.992(4)
_cell_angle_gamma                79.519(4)
_cell_volume                     2630.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.08
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.0879 before and 0.0728 after correction.
        The Ratio of minimum to maximum transmission is 0.8807.
        The λ/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_source                   'sealed tube'
_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.1178
_diffrn_reflns_number            26776
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         0.83
_diffrn_reflns_theta_max         25.48
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.962
_reflns_number_total             9406
_reflns_number_gt                2473
_reflns_threshold_expression     >2sigma(I)
_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
;
#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_structure_solution    
;
        SHELXS, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         9406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2986
_refine_ls_R_factor_gt           0.0712
_refine_ls_restrained_S_all      0.906
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0726P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1421
_refine_ls_wR_factor_ref         0.2264
#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#
_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.
;
_atom_sites_solution_hydrogens   geom
#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
_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
O1 O 0.3679(4) 0.8349(3) 0.27820(16) 0.0881(12) Uani 1 1 d . . .
O2 O 0.9319(5) 0.2207(4) 0.32259(18) 0.1079(14) Uani 1 1 d . . .
O3 O 0.7992(6) 0.3822(4) 0.42818(16) 0.1079(15) Uani 1 1 d . . .
O4 O 0.4725(6) 0.4360(5) 0.4453(2) 0.1243(17) Uani 1 1 d . . .
O5 O 0.2649(5) 0.5782(4) 0.36704(16) 0.0947(13) Uani 1 1 d . . .
O6 O 0.8120(4) 0.8814(3) 0.13250(16) 0.0843(12) Uani 1 1 d . . .
O7 O 1.3661(5) 0.2683(4) 0.24477(18) 0.1166(15) Uani 1 1 d . . .
O8 O 1.2545(5) 0.3959(4) 0.10350(14) 0.0950(13) Uani 1 1 d . . .
O9 O 0.9348(5) 0.4491(4) 0.07337(19) 0.0988(13) Uani 1 1 d . . .
O10 O 0.7139(5) 0.6136(3) 0.10992(15) 0.0819(11) Uani 1 1 d . . .
C1 C 0.3772(8) 0.7585(6) 0.2436(2) 0.096(2) Uani 1 1 d . . .
C2 C 0.5097(10) 0.6611(7) 0.2559(3) 0.085(2) Uani 1 1 d . . .
C3 C 0.6118(11) 0.5833(7) 0.2646(3) 0.087(2) Uani 1 1 d . . .
C4 C 0.7320(10) 0.4931(7) 0.2751(3) 0.085(2) Uani 1 1 d . . .
C5 C 0.8372(10) 0.4181(7) 0.2859(3) 0.091(2) Uani 1 1 d . . .
C6 C 0.9701(8) 0.3256(6) 0.3007(3) 0.110(2) Uani 1 1 d . . .
C7 C 0.8568(8) 0.2169(5) 0.3738(3) 0.0869(19) Uani 1 1 d . . .
C8 C 0.9617(8) 0.2201(6) 0.4191(3) 0.0775(17) Uani 1 1 d . . .
C9 C 1.0907(11) 0.1382(7) 0.4347(4) 0.122(3) Uani 1 1 d . . .
C10 C 1.1754(11) 0.1372(8) 0.4790(5) 0.153(4) Uani 1 1 d . . .
C11 C 1.1358(10) 0.2174(9) 0.5082(3) 0.127(3) Uani 1 1 d . . .
C12 C 1.0093(10) 0.3011(6) 0.4931(3) 0.096(2) Uani 1 1 d . . .
C13 C 0.9225(8) 0.3014(6) 0.4481(3) 0.0772(18) Uani 1 1 d . . .
C14 C 0.7297(8) 0.4600(6) 0.4593(2) 0.0936(19) Uani 1 1 d . . .
C15 C 0.5752(9) 0.5135(5) 0.4337(3) 0.101(2) Uani 1 1 d . . .
C16 C 0.4165(11) 0.4040(5) 0.4024(4) 0.125(3) Uani 1 1 d . . .
C17 C 0.2538(8) 0.4651(6) 0.3874(2) 0.098(2) Uani 1 1 d . . .
C18 C 0.1349(9) 0.6560(6) 0.3537(2) 0.0744(17) Uani 1 1 d . . .
C19 C -0.0159(11) 0.6341(7) 0.3568(2) 0.097(2) Uani 1 1 d . . .
C20 C -0.1403(9) 0.7181(10) 0.3426(3) 0.106(3) Uani 1 1 d . . .
C21 C -0.1160(10) 0.8266(8) 0.3253(3) 0.104(2) Uani 1 1 d . . .
C22 C 0.0340(11) 0.8477(6) 0.3217(2) 0.092(2) Uani 1 1 d . . .
C23 C 0.1607(8) 0.7643(6) 0.3364(2) 0.0715(17) Uani 1 1 d . . .
C24 C 0.3255(7) 0.7900(5) 0.3328(2) 0.0724(16) Uani 1 1 d . . .
C25 C 0.3478(7) 0.8764(5) 0.3649(2) 0.0890(18) Uani 1 1 d . . .
C26 C 0.3159(9) 0.8415(5) 0.4234(3) 0.109(2) Uani 1 1 d . . .
C27 C 0.4066(10) 0.8244(6) 0.4614(3) 0.140(3) Uani 1 1 d . . .
C28 C 0.7851(9) 0.1085(5) 0.3854(3) 0.121(3) Uani 1 1 d . . .
C29 C 0.6582(14) 0.1188(7) 0.3489(4) 0.158(4) Uani 1 1 d . . .
C30 C 0.5181(13) 0.1106(7) 0.3677(4) 0.182(4) Uani 1 1 d . . .
C31 C 0.8152(7) 0.8147(6) 0.1859(2) 0.096(2) Uani 1 1 d . . .
C32 C 0.9404(8) 0.7183(7) 0.1954(2) 0.080(2) Uani 1 1 d . . .
C33 C 1.0377(9) 0.6396(7) 0.2061(2) 0.078(2) Uani 1 1 d . . .
C34 C 1.1559(9) 0.5468(7) 0.2171(2) 0.080(2) Uani 1 1 d . . .
C35 C 1.2609(9) 0.4694(6) 0.2251(2) 0.081(2) Uani 1 1 d . . .
C36 C 1.3968(8) 0.3765(6) 0.2350(3) 0.101(2) Uani 1 1 d . . .
C37 C 1.2996(8) 0.2414(5) 0.2005(3) 0.095(2) Uani 1 1 d . . .
C38 C 1.4136(8) 0.2402(5) 0.1522(3) 0.086(2) Uani 1 1 d . . .
C39 C 1.5494(10) 0.1617(6) 0.1543(3) 0.120(3) Uani 1 1 d . . .
C40 C 1.6474(9) 0.1594(7) 0.1103(4) 0.126(3) Uani 1 1 d . . .
C41 C 1.6135(9) 0.2350(8) 0.0623(4) 0.117(3) Uani 1 1 d . . .
C42 C 1.4817(9) 0.3154(6) 0.0583(3) 0.0940(19) Uani 1 1 d . . .
C43 C 1.3837(8) 0.3181(6) 0.1037(3) 0.0803(18) Uani 1 1 d . . .
C44 C 1.1973(7) 0.4711(5) 0.0543(2) 0.0832(17) Uani 1 1 d . . .
C45 C 1.0366(8) 0.5274(5) 0.0665(2) 0.0859(18) Uani 1 1 d . . .
C46 C 0.8561(8) 0.4310(5) 0.1232(3) 0.104(2) Uani 1 1 d . . .
C47 C 0.6969(7) 0.5005(5) 0.1191(2) 0.0867(18) Uani 1 1 d . . .
C48 C 0.5846(8) 0.6955(6) 0.1031(2) 0.0694(16) Uani 1 1 d . . .
C49 C 0.4338(9) 0.6744(5) 0.1063(2) 0.0820(18) Uani 1 1 d . . .
C50 C 0.3088(8) 0.7608(8) 0.0990(2) 0.088(2) Uani 1 1 d . . .
C51 C 0.3337(9) 0.8684(7) 0.0899(2) 0.088(2) Uani 1 1 d . . .
C52 C 0.4835(9) 0.8903(5) 0.0876(2) 0.0854(18) Uani 1 1 d . . .
C53 C 0.6147(7) 0.8038(5) 0.09419(19) 0.0617(15) Uani 1 1 d . . .
C54 C 0.7821(6) 0.8262(4) 0.0917(2) 0.0696(16) Uani 1 1 d . . .
C55 C 0.8194(6) 0.9008(5) 0.0377(2) 0.0806(17) Uani 1 1 d . . .
C56 C 0.8143(8) 0.8466(5) -0.0090(3) 0.0936(19) Uani 1 1 d . . .
C57 C 0.9353(9) 0.8165(5) -0.0379(3) 0.132(3) Uani 1 1 d . . .
C58 C 1.2494(10) 0.1275(6) 0.2236(3) 0.138(3) Uani 1 1 d . . .
C59 C 1.1585(16) 0.0943(8) 0.1916(5) 0.196(5) Uani 1 1 d . . .
C60 C 1.0260(14) 0.0735(9) 0.1926(4) 0.244(7) Uani 1 1 d . . .
H1A H 0.3878 0.7982 0.2065 0.115 Uiso 1 1 calc R . .
H1B H 0.2797 0.7304 0.2459 0.115 Uiso 1 1 calc R . .
H6A H 1.0331 0.3201 0.2686 0.132 Uiso 1 1 calc R . .
H6B H 1.0346 0.3441 0.3268 0.132 Uiso 1 1 calc R . .
H7 H 0.7709 0.2809 0.3703 0.104 Uiso 1 1 calc R . .
H9 H 1.12 0.0833 0.4147 0.147 Uiso 1 1 calc R . .
H10 H 1.2614 0.081 0.4895 0.183 Uiso 1 1 calc R . .
H11 H 1.1944 0.2157 0.5386 0.153 Uiso 1 1 calc R . .
H12 H 0.9824 0.3567 0.5128 0.115 Uiso 1 1 calc R . .
H14A H 0.795 0.5154 0.459 0.112 Uiso 1 1 calc R . .
H14B H 0.7163 0.4225 0.4965 0.112 Uiso 1 1 calc R . .
H15A H 0.5331 0.5791 0.4479 0.121 Uiso 1 1 calc R . .
H15B H 0.5871 0.5364 0.3948 0.121 Uiso 1 1 calc R . .
H16A H 0.4164 0.3245 0.4116 0.15 Uiso 1 1 calc R . .
H16B H 0.4849 0.4186 0.3715 0.15 Uiso 1 1 calc R . .
H17A H 0.2107 0.435 0.36 0.118 Uiso 1 1 calc R . .
H17B H 0.1864 0.458 0.419 0.118 Uiso 1 1 calc R . .
H19 H -0.0324 0.5613 0.3686 0.116 Uiso 1 1 calc R . .
H20 H -0.2413 0.7027 0.3447 0.128 Uiso 1 1 calc R . .
H21 H -0.2006 0.8847 0.3162 0.125 Uiso 1 1 calc R . .
H22 H 0.0502 0.9204 0.3089 0.11 Uiso 1 1 calc R . .
H24 H 0.3991 0.7209 0.3466 0.087 Uiso 1 1 calc R . .
H25A H 0.4545 0.8897 0.3604 0.107 Uiso 1 1 calc R . .
H25B H 0.2785 0.9459 0.3504 0.107 Uiso 1 1 calc R . .
H26 H 0.2141 0.8313 0.4323 0.131 Uiso 1 1 calc R . .
H27A H 0.51 0.8333 0.4551 0.168 Uiso 1 1 calc R . .
H27B H 0.3721 0.8026 0.4967 0.168 Uiso 1 1 calc R . .
H28A H 0.8652 0.0457 0.3814 0.145 Uiso 1 1 calc R . .
H28B H 0.7476 0.0947 0.4225 0.145 Uiso 1 1 calc R . .
H29 H 0.6758 0.1312 0.3117 0.189 Uiso 1 1 calc R . .
H30A H 0.5005 0.0981 0.4049 0.218 Uiso 1 1 calc R . .
H30B H 0.4358 0.1172 0.3439 0.218 Uiso 1 1 calc R . .
H31A H 0.7159 0.7893 0.1929 0.115 Uiso 1 1 calc R . .
H31B H 0.826 0.8606 0.2116 0.115 Uiso 1 1 calc R . .
H36A H 1.4652 0.3859 0.2038 0.122 Uiso 1 1 calc R . .
H36B H 1.4545 0.3838 0.2659 0.122 Uiso 1 1 calc R . .
H37 H 1.2057 0.2971 0.1887 0.114 Uiso 1 1 calc R . .
H39 H 1.5752 0.1092 0.1863 0.144 Uiso 1 1 calc R . .
H40 H 1.7379 0.1057 0.1132 0.151 Uiso 1 1 calc R . .
H41 H 1.6795 0.2318 0.0327 0.141 Uiso 1 1 calc R . .
H42 H 1.4574 0.3674 0.0261 0.113 Uiso 1 1 calc R . .
H44A H 1.1929 0.4307 0.0257 0.1 Uiso 1 1 calc R . .
H44B H 1.2649 0.5255 0.0428 0.1 Uiso 1 1 calc R . .
H45A H 1.039 0.5558 0.0993 0.103 Uiso 1 1 calc R . .
H45B H 0.9999 0.5897 0.037 0.103 Uiso 1 1 calc R . .
H46A H 0.9158 0.4492 0.1508 0.124 Uiso 1 1 calc R . .
H46B H 0.8477 0.3529 0.1341 0.124 Uiso 1 1 calc R . .
H47A H 0.6395 0.488 0.0894 0.104 Uiso 1 1 calc R . .
H47B H 0.6396 0.481 0.1524 0.104 Uiso 1 1 calc R . .
H49 H 0.4168 0.6012 0.1135 0.098 Uiso 1 1 calc R . .
H50 H 0.2073 0.7464 0.1003 0.106 Uiso 1 1 calc R . .
H51 H 0.2489 0.927 0.0852 0.106 Uiso 1 1 calc R . .
H52 H 0.4984 0.9638 0.0817 0.103 Uiso 1 1 calc R . .
H54 H 0.8545 0.7548 0.0965 0.084 Uiso 1 1 calc R . .
H55A H 0.7445 0.97 0.0316 0.097 Uiso 1 1 calc R . .
H55B H 0.9228 0.9186 0.04 0.097 Uiso 1 1 calc R . .
H56 H 0.718 0.8331 -0.0182 0.112 Uiso 1 1 calc R . .
H57A H 1.0334 0.8287 -0.0298 0.158 Uiso 1 1 calc R . .
H57B H 0.9235 0.7829 -0.0666 0.158 Uiso 1 1 calc R . .
H58A H 1.343 0.0711 0.2319 0.166 Uiso 1 1 calc R . .
H58B H 1.1948 0.1316 0.2575 0.166 Uiso 1 1 calc R . .
H59 H 1.2093 0.084 0.1596 0.235 Uiso 1 1 calc R . .
H60A H 0.9623 0.0805 0.2225 0.293 Uiso 1 1 calc R . .
H60B H 0.9891 0.0507 0.1634 0.293 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
O1 C1 1.415(6) . ?
O1 C24 1.435(5) . ?
O2 C6 1.402(6) . ?
O2 C7 1.423(6) . ?
O3 C13 1.358(7) . ?
O3 C14 1.415(6) . ?
O4 C15 1.412(7) . ?
O4 C16 1.364(8) . ?
O5 C17 1.416(6) . ?
O5 C18 1.349(6) . ?
O6 C31 1.424(6) . ?
O6 C54 1.412(5) . ?
O7 C36 1.393(6) . ?
O7 C37 1.404(7) . ?
O8 C43 1.344(6) . ?
O8 C44 1.429(5) . ?
O9 C45 1.415(6) . ?
O9 C46 1.406(6) . ?
O10 C47 1.415(6) . ?
O10 C48 1.364(6) . ?
C2 C1 1.502(9) . ?
C3 C2 1.178(9) . ?
C4 C3 1.375(9) . ?
C4 C5 1.176(9) . ?
C5 C6 1.473(9) . ?
C7 C28 1.559(8) . ?
C8 C7 1.498(8) . ?
C8 C9 1.378(8) . ?
C8 C13 1.363(7) . ?
C9 C10 1.358(10) . ?
C11 C10 1.354(10) . ?
C12 C11 1.374(8) . ?
C13 C12 1.385(8) . ?
C14 C15 1.488(7) . ?
C17 C16 1.499(8) . ?
C18 C19 1.383(8) . ?
C18 C23 1.385(7) . ?
C19 C20 1.361(8) . ?
C21 C20 1.384(8) . ?
C22 C21 1.373(8) . ?
C23 C22 1.372(7) . ?
C23 C24 1.520(7) . ?
C25 C24 1.522(7) . ?
C25 C26 1.478(8) . ?
C26 C27 1.222(7) . ?
C28 C29 1.433(11) . ?
C29 C30 1.306(10) . ?
C32 C31 1.452(8) . ?
C33 C32 1.163(8) . ?
C33 C34 1.387(9) . ?
C35 C34 1.190(8) . ?
C35 C36 1.483(8) . ?
C37 C58 1.551(8) . ?
C38 C37 1.545(8) . ?
C38 C39 1.385(8) . ?
C38 C43 1.388(7) . ?
C39 C40 1.377(9) . ?
C41 C40 1.371(9) . ?
C42 C41 1.370(8) . ?
C43 C42 1.406(7) . ?
C44 C45 1.499(7) . ?
C47 C46 1.488(7) . ?
C48 C49 1.379(7) . ?
C49 C50 1.371(7) . ?
C51 C50 1.369(7) . ?
C52 C51 1.375(7) . ?
C53 C48 1.393(7) . ?
C53 C52 1.408(7) . ?
C53 C54 1.528(7) . ?
C54 C55 1.537(6) . ?
C55 C56 1.483(7) . ?
C56 C57 1.304(7) . ?
C58 C59 1.326(10) . ?
C59 C60 1.223(12) . ?


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
O1 C1 C2 114.9(5) . . ?
C3 C2 C1 178.1(9) . . ?
C2 C3 C4 179.3(9) . . ?
C5 C4 C3 176.9(9) . . ?
C4 C5 C6 178.3(9) . . ?
O2 C6 C5 116.0(6) . . ?
C8 C7 C28 111.6(6) . . ?
O2 C7 C8 114.5(5) . . ?
O2 C7 C28 105.8(5) . . ?
C9 C8 C7 121.6(8) . . ?
C13 C8 C7 119.2(7) . . ?
C13 C8 C9 119.1(7) . . ?
C10 C9 C8 120.4(8) . . ?
C11 C10 C9 120.6(9) . . ?
C10 C11 C12 120.2(9) . . ?
C11 C12 C13 119.0(8) . . ?
C8 C13 C12 120.6(7) . . ?
O3 C13 C8 115.2(7) . . ?
O3 C13 C12 124.1(7) . . ?
O3 C14 C15 106.5(5) . . ?
O4 C15 C14 108.7(5) . . ?
O4 C16 C17 111.4(6) . . ?
O5 C17 C16 106.8(5) . . ?
C19 C18 C23 120.2(7) . . ?
O5 C18 C19 124.7(7) . . ?
O5 C18 C23 115.1(7) . . ?
C20 C19 C18 120.6(8) . . ?
C19 C20 C21 119.8(8) . . ?
C22 C21 C20 119.4(7) . . ?
C23 C22 C21 121.6(7) . . ?
C18 C23 C24 120.9(6) . . ?
C22 C23 C18 118.4(6) . . ?
C22 C23 C24 120.7(7) . . ?
C23 C24 C25 113.4(5) . . ?
O1 C24 C23 112.1(4) . . ?
O1 C24 C25 105.1(5) . . ?
C26 C25 C24 112.8(5) . . ?
C27 C26 C25 128.1(8) . . ?
C29 C28 C7 110.5(6) . . ?
C30 C29 C28 120.1(11) . . ?
C1 O1 C24 113.4(4) . . ?
C6 O2 C7 112.2(5) . . ?
C13 O3 C14 120.6(5) . . ?
C16 O4 C15 117.3(6) . . ?
C18 O5 C17 120.6(5) . . ?
O6 C31 C32 114.1(5) . . ?
C33 C32 C31 175.9(7) . . ?
C32 C33 C34 178.1(7) . . ?
C35 C34 C33 177.4(7) . . ?
C34 C35 C36 177.3(8) . . ?
O7 C36 C35 117.4(6) . . ?
C38 C37 C58 113.9(6) . . ?
O7 C37 C38 112.0(5) . . ?
O7 C37 C58 104.8(6) . . ?
C39 C38 C37 122.4(7) . . ?
C39 C38 C43 116.3(7) . . ?
C43 C38 C37 121.3(6) . . ?
C40 C39 C38 121.8(8) . . ?
C41 C40 C39 121.0(8) . . ?
C42 C41 C40 119.6(8) . . ?
C41 C42 C43 119.0(7) . . ?
C38 C43 C42 122.3(7) . . ?
O8 C43 C38 115.1(6) . . ?
O8 C43 C42 122.6(7) . . ?
O8 C44 C45 106.3(4) . . ?
O9 C45 C44 108.7(5) . . ?
O9 C46 C47 111.0(5) . . ?
O10 C47 C46 108.0(5) . . ?
C49 C48 C53 121.5(6) . . ?
O10 C48 C49 123.3(6) . . ?
O10 C48 C53 115.2(6) . . ?
C50 C49 C48 120.3(6) . . ?
C51 C50 C49 119.9(7) . . ?
C50 C51 C52 120.3(6) . . ?
C51 C52 C53 121.4(6) . . ?
C48 C53 C52 116.6(6) . . ?
C48 C53 C54 121.1(6) . . ?
C52 C53 C54 122.3(6) . . ?
C53 C54 C55 113.0(4) . . ?
O6 C54 C53 111.9(4) . . ?
O6 C54 C55 105.8(4) . . ?
C56 C55 C54 112.3(5) . . ?
C57 C56 C55 124.6(7) . . ?
C59 C58 C37 115.6(7) . . ?
C60 C59 C58 137.5(15) . . ?
C54 O6 C31 113.9(4) . . ?
C36 O7 C37 114.2(5) . . ?
C43 O8 C44 120.9(5) . . ?
C46 O9 C45 116.4(5) . . ?
C48 O10 C47 119.9(5) . . ?


_database_code_depnum_ccdc_archive 'CCDC 970708'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sk_sci75_0m

_audit_creation_date             2014-03-06T15:53:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H23 N O5'
_chemical_formula_sum            'C22 H23 N O5'
_chemical_formula_weight         381.41

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.4541(10)
_cell_length_b                   17.4437(17)
_cell_length_c                   11.0894(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.244(5)
_cell_angle_gamma                90
_cell_volume                     1960.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.293
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0535 before and 0.0338 after correction.
        The Ratio of minimum to maximum transmission is 0.8918.
        The λ/2 correction factor is 0.0015.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_number            14425
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.125
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_number_total             3493
_reflns_number_gt                2536
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0781P)²+1.0033P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3493
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1834
_refine_ls_wR_factor_gt          0.1675
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.4066(2) 0.10882(13) 0.0916(2) 0.0844(6) Uani 1 d . .
O2A O 0.4636(4) 0.1274(2) 0.6303(3) 0.0515(8) Uani 0.5 d A 1
O2B O 0.4507(5) 0.0655(5) 0.6047(5) 0.1114(19) Uani 0.5 d A 2
O3 O 0.13276(17) 0.08161(11) 0.48455(16) 0.0639(5) Uani 1 d . .
O4 O 0.10310(18) 0.04586(10) 0.22737(16) 0.0636(5) Uani 1 d . .
O5 O 0.7281(2) 0.16918(18) 0.4105(2) 0.1066(9) Uani 1 d . .
N1 N 0.6749(3) 0.1824(2) 0.2809(3) 0.1103(11) Uani 1 d . .
C1 C 0.4667(3) 0.1792(2) 0.1333(3) 0.0820(9) Uani 1 d . .
H1A H 0.3992 0.2177 0.1314 0.098 Uiso 1 calc . .
H1B H 0.5203 0.1958 0.0782 0.098 Uiso 1 calc . .
C2 C 0.5515(3) 0.17196(18) 0.2633(3) 0.0749(8) Uani 1 d . .
C3 C 0.5175(3) 0.1523(2) 0.3761(3) 0.0862(10) Uani 1 d . .
H3 H 0.4336 0.1422 0.3868 0.103 Uiso 1 calc . .
C4 C 0.6298(3) 0.1513(2) 0.4622(3) 0.0809(9) Uani 1 d . .
C5 C 0.6701(3) 0.1321(3) 0.5959(3) 0.1022(13) Uani 1 d . .
H5A H 0.7479 0.0998 0.6102 0.123 Uiso 1 calc . .
H5B H 0.6948 0.1791 0.6425 0.123 Uiso 1 calc . .
C6 C 0.5716(4) 0.0938(3) 0.6440(4) 0.1233(17) Uani 1 d . .
H6AA H 0.5551 0.0439 0.6044 0.148 Uiso 0.5 calc A 1
H6AB H 0.6076 0.085 0.7323 0.148 Uiso 0.5 calc A 1
H6BC H 0.6201 0.0502 0.6867 0.148 Uiso 0.5 calc A 2
H6BD H 0.5619 0.1281 0.71 0.148 Uiso 0.5 calc A 2
C7A C 0.3660(15) 0.0832(4) 0.6724(14) 0.073(2) Uani 0.5 d A 1
H7AA H 0.3396 0.0402 0.6163 0.088 Uiso 0.5 calc A 1
H7AB H 0.4068 0.0625 0.754 0.088 Uiso 0.5 calc A 1
C7B C 0.3623(15) 0.0489(5) 0.6696(14) 0.073(2) Uani 0.5 d A 2
H7BA H 0.409 0.034 0.7531 0.088 Uiso 0.5 calc A 2
H7BB H 0.3106 0.0052 0.6314 0.088 Uiso 0.5 calc A 2
C8 C 0.2584(3) 0.12160(18) 0.6795(2) 0.0691(8) Uani 1 d . .
C9 C 0.2718(4) 0.1687(2) 0.7839(3) 0.0902(11) Uani 1 d . .
H9 H 0.3465 0.1636 0.8493 0.108 Uiso 1 calc . .
C10 C 0.1784(4) 0.2221(2) 0.7931(3) 0.0948(11) Uani 1 d . .
H10 H 0.1903 0.2532 0.8631 0.114 Uiso 1 calc . .
C11 C 0.0678(4) 0.22919(19) 0.6979(3) 0.0887(10) Uani 1 d . .
H11 H 0.0039 0.2652 0.7034 0.106 Uiso 1 calc . .
C12 C 0.0502(3) 0.18365(16) 0.5942(3) 0.0695(7) Uani 1 d . .
H12 H -0.0257 0.1889 0.5301 0.083 Uiso 1 calc . .
C13 C 0.1448(3) 0.12979(15) 0.5844(2) 0.0563(6) Uani 1 d . .
C14 C 0.0101(3) 0.08237(16) 0.3924(2) 0.0599(7) Uani 1 d . .
H14A H -0.004 0.1322 0.3524 0.072 Uiso 1 calc . .
H14B H -0.0622 0.0722 0.4307 0.072 Uiso 1 calc . .
C15 C 0.0154(3) 0.02215(15) 0.2991(2) 0.0607(7) Uani 1 d . .
H15A H 0.0457 -0.0258 0.3409 0.073 Uiso 1 calc . .
H15B H -0.0719 0.014 0.2454 0.073 Uiso 1 calc . .
C16 C 0.1354(2) -0.00541(15) 0.1470(2) 0.0568(6) Uani 1 d . .
C17 C 0.0823(3) -0.07811(17) 0.1258(3) 0.0745(8) Uani 1 d . .
H17 H 0.0186 -0.0948 0.1654 0.089 Uiso 1 calc . .
C18 C 0.1260(4) -0.1256(2) 0.0444(4) 0.1006(12) Uani 1 d . .
H18 H 0.0921 -0.1749 0.0295 0.121 Uiso 1 calc . .
C19 C 0.2195(5) -0.1001(3) -0.0144(3) 0.1034(13) Uani 1 d . .
H19 H 0.2479 -0.1322 -0.0695 0.124 Uiso 1 calc . .
C20 C 0.2710(4) -0.0278(2) 0.0076(3) 0.0877(10) Uani 1 d . .
H20 H 0.3349 -0.0115 -0.032 0.105 Uiso 1 calc . .
C21 C 0.2296(3) 0.02086(16) 0.0873(2) 0.0644(7) Uani 1 d . .
C22 C 0.2824(3) 0.10096(18) 0.1142(3) 0.0838(9) Uani 1 d . .
H22A H 0.2221 0.1369 0.0626 0.101 Uiso 1 calc . .
H22B H 0.2874 0.1133 0.2006 0.101 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C22 1.389(4) . ?
O1 C1 1.404(4) . ?
O2A C6 1.248(6) . ?
O2A C7A 1.446(16) . ?
O2B C6 1.327(6) . ?
O2B C7B 1.335(18) . ?
O3 C13 1.371(3) . ?
O3 C14 1.430(3) . ?
O4 C16 1.362(3) . ?
O4 C15 1.415(3) . ?
O5 C4 1.331(4) . ?
O5 N1 1.426(4) . ?
N1 C2 1.269(4) . ?
C1 C2 1.501(4) . ?
C2 C3 1.424(4) . ?
C3 C4 1.319(4) . ?
C4 C5 1.476(5) . ?
C5 C6 1.437(5) . ?
C7A C8 1.328(14) . ?
C7B C8 1.690(11) . ?
C8 C13 1.388(4) . ?
C8 C9 1.398(5) . ?
C9 C10 1.371(5) . ?
C10 C11 1.366(5) . ?
C11 C12 1.372(4) . ?
C12 C13 1.388(4) . ?
C14 C15 1.485(4) . ?
C16 C17 1.381(4) . ?
C16 C21 1.393(4) . ?
C17 C18 1.383(5) . ?
C18 C19 1.376(6) . ?
C19 C20 1.369(5) . ?
C20 C21 1.369(4) . ?
C21 C22 1.505(4) . ?

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
C22 O1 C1 112.9(2) . . ?
C6 O2A C7A 113.5(5) . . ?
C6 O2B C7B 129.3(7) . . ?
C13 O3 C14 117.4(2) . . ?
C16 O4 C15 118.33(19) . . ?
C4 O5 N1 108.7(2) . . ?
C2 N1 O5 105.2(3) . . ?
O1 C1 C2 110.7(3) . . ?
N1 C2 C3 111.3(3) . . ?
N1 C2 C1 118.3(3) . . ?
C3 C2 C1 130.4(3) . . ?
C4 C3 C2 105.6(3) . . ?
C3 C4 O5 109.2(3) . . ?
C3 C4 C5 135.5(3) . . ?
O5 C4 C5 115.2(3) . . ?
C6 C5 C4 115.2(3) . . ?
O2A C6 C5 116.4(4) . . ?
O2B C6 C5 139.7(4) . . ?
C8 C7A O2A 115.2(6) . . ?
O2B C7B C8 114.4(8) . . ?
C7A C8 C13 125.9(7) . . ?
C7A C8 C9 115.6(6) . . ?
C13 C8 C9 117.5(3) . . ?
C13 C8 C7B 118.1(5) . . ?
C9 C8 C7B 124.0(5) . . ?
C10 C9 C8 122.2(3) . . ?
C11 C10 C9 119.1(3) . . ?
C10 C11 C12 120.6(3) . . ?
C11 C12 C13 120.4(3) . . ?
O3 C13 C12 123.6(2) . . ?
O3 C13 C8 116.2(2) . . ?
C12 C13 C8 120.2(3) . . ?
O3 C14 C15 108.1(2) . . ?
O4 C15 C14 109.0(2) . . ?
O4 C16 C17 124.1(2) . . ?
O4 C16 C21 114.4(2) . . ?
C17 C16 C21 121.5(3) . . ?
C16 C17 C18 118.6(3) . . ?
C19 C18 C17 120.2(3) . . ?
C20 C19 C18 120.5(3) . . ?
C19 C20 C21 120.9(3) . . ?
C20 C21 C16 118.4(3) . . ?
C20 C21 C22 123.0(3) . . ?
C16 C21 C22 118.6(2) . . ?
O1 C22 C21 111.7(3) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 970709'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nm1066

_audit_creation_date             2014-03-06T15:55:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H26 O5 S'
_chemical_formula_sum            'C24 H26 O5 S'
_chemical_formula_weight         426.51

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_Int_Tables_number      62
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
'x-1/2, y, -z-1/2'

_cell_length_a                   9.5532(5)
_cell_length_b                   24.2453(13)
_cell_length_c                   9.5232(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2205.77(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    794
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      20.12

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             904
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0654 before and 0.0581 after correction.
        The Ratio of minimum to maximum transmission is 0.9147.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6819
_exptl_absorpt_correction_T_max  0.7455

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_number            9531
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         25.014
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.99
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.99
_reflns_number_total             1973
_reflns_number_gt                906
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    
;
        XS, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_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.
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0084(11)
_refine_ls_number_reflns         1973
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1507
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.0945
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.959
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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
S1 S -0.14497(16) 0.75 0.13826(13) 0.0752(5) Uani 1 d . .
O1 O -0.1108(2) 0.87794(9) 0.2647(2) 0.0720(8) Uani 1 d . .
O2 O 0.1194(2) 0.85866(8) 0.62517(19) 0.0478(6) Uani 1 d . .
O3 O 0.1959(3) 0.75 0.7332(3) 0.0478(8) Uani 1 d . .
C1 C 0.1063(4) 0.77895(14) 0.1042(3) 0.0717(12) Uani 1 d . .
H1 H 0.187 0.8 0.0933 0.086 Uiso 1 calc . .
C2 C -0.0219(4) 0.80113(16) 0.1215(3) 0.0624(10) Uani 1 d . .
C3 C -0.0597(5) 0.86055(16) 0.1305(4) 0.0825(13) Uani 1 d . .
H3A H 0.0223 0.8823 0.1073 0.099 Uiso 1 calc . .
H3B H -0.1306 0.8683 0.0604 0.099 Uiso 1 calc . .
C4 C -0.0099(3) 0.87108(13) 0.3723(3) 0.0574(10) Uani 1 d . .
H4A H 0.0821 0.8809 0.3373 0.069 Uiso 1 calc . .
H4B H -0.0075 0.8328 0.402 0.069 Uiso 1 calc . .
C5 C -0.0474(3) 0.90734(12) 0.4948(3) 0.0435(8) Uani 1 d . .
C6 C -0.1449(4) 0.94920(14) 0.4841(4) 0.0593(10) Uani 1 d . .
H6 H -0.1927 0.9543 0.4 0.071 Uiso 1 calc . .
C7 C -0.1727(4) 0.98379(15) 0.5968(4) 0.0681(11) Uani 1 d . .
H7 H -0.2393 1.0116 0.5887 0.082 Uiso 1 calc . .
C8 C -0.1010(4) 0.97657(15) 0.7204(4) 0.0646(11) Uani 1 d . .
H8 H -0.1189 0.9999 0.7958 0.077 Uiso 1 calc . .
C9 C -0.0033(3) 0.93548(13) 0.7342(3) 0.0516(9) Uani 1 d . .
H9 H 0.0449 0.931 0.8183 0.062 Uiso 1 calc . .
C10 C 0.0232(3) 0.90063(12) 0.6219(3) 0.0421(8) Uani 1 d . .
C11 C 0.1832(3) 0.84697(12) 0.7578(3) 0.0468(9) Uani 1 d . .
H11A H 0.1115 0.8392 0.8271 0.056 Uiso 1 calc . .
H11B H 0.2363 0.8788 0.7893 0.056 Uiso 1 calc . .
C12 C 0.2780(3) 0.79845(12) 0.7434(3) 0.0483(8) Uani 1 d . .
H12A H 0.3354 0.8024 0.66 0.058 Uiso 1 calc . .
H12B H 0.3393 0.7961 0.8243 0.058 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
S1 C2 1.716(4) . ?
S1 C2 1.716(4) 7_575 ?
O1 C3 1.432(4) . ?
O1 C4 1.417(3) . ?
O2 C10 1.372(3) . ?
O2 C11 1.431(3) . ?
O3 C12 1.415(3) 7_575 ?
O3 C12 1.416(3) . ?
C1 C1 1.404(7) 7_575 ?
C1 H1 0.93 . ?
C1 C2 1.347(4) . ?
C2 C3 1.488(5) . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C4 C5 1.504(4) . ?
C5 C6 1.381(4) . ?
C5 C10 1.396(4) . ?
C6 H6 0.93 . ?
C6 C7 1.388(4) . ?
C7 H7 0.93 . ?
C7 C8 1.373(4) . ?
C8 H8 0.93 . ?
C8 C9 1.372(4) . ?
C9 H9 0.93 . ?
C9 C10 1.386(4) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C11 C12 1.490(4) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?

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 S1 C2 92.5(3) . 7_575 ?
C4 O1 C3 112.3(3) . . ?
C10 O2 C11 116.9(2) . . ?
C12 O3 C12 112.2(3) 7_575 . ?
C1 C1 H1 123.2 7_575 . ?
C2 C1 C1 113.5(2) . 7_575 ?
C2 C1 H1 123.2 . . ?
C1 C2 S1 110.2(3) . . ?
C1 C2 C3 127.9(4) . . ?
C3 C2 S1 121.9(3) . . ?
O1 C3 C2 114.8(3) . . ?
O1 C3 H3A 108.6 . . ?
O1 C3 H3B 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.5 . . ?
O1 C4 H4A 109.8 . . ?
O1 C4 H4B 109.8 . . ?
O1 C4 C5 109.3(3) . . ?
H4A C4 H4B 108.3 . . ?
C5 C4 H4A 109.8 . . ?
C5 C4 H4B 109.8 . . ?
C6 C5 C4 122.2(3) . . ?
C6 C5 C10 118.4(3) . . ?
C10 C5 C4 119.3(3) . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.1(3) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.4(3) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.5(3) . . ?
C10 C9 H9 120.2 . . ?
O2 C10 C5 115.5(3) . . ?
O2 C10 C9 123.9(3) . . ?
C9 C10 C5 120.7(3) . . ?
O2 C11 H11A 109.8 . . ?
O2 C11 H11B 109.8 . . ?
O2 C11 C12 109.5(2) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
O3 C12 C11 109.0(2) . . ?
O3 C12 H12A 109.9 . . ?
O3 C12 H12B 109.9 . . ?
C11 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 970710'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nm1097a2_06
_audit_creation_date             2014-02-17T20:07:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C26 H30 O4 S'
_chemical_formula_sum            'C26 H30 O4 S'
_chemical_formula_weight         438.56

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9442(9)
_cell_length_b                   9.7734(10)
_cell_length_c                   14.2491(12)
_cell_angle_alpha                85.521(5)
_cell_angle_beta                 75.471(5)
_cell_angle_gamma                75.776(5)
_cell_volume                     1168.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1139
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      17.88

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       iiregular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_F_000             468
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0605 before and 0.0395 after correction.
        The Ratio of minimum to maximum transmission is 0.8491.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6336
_exptl_absorpt_correction_T_max  0.7462
_shelx_estimated_absorpt_T_min   0.554
_shelx_estimated_absorpt_T_max   0.967

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_number            7592
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.477
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_number_total             4126
_reflns_number_gt                1652
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_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.
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1974P)²+0.1908P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4126
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2061
_refine_ls_R_factor_gt           0.104
_refine_ls_wR_factor_ref         0.3841
_refine_ls_wR_factor_gt          0.3027
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_restrained_S_all      1.06
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.054

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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
C1 C 0.4176(10) 0.3271(11) 0.8817(6) 0.153(2) Uani 1 d . .
H1A H 0.4942 0.3828 0.8804 0.183 Uiso 1 calc . .
H1B H 0.474 0.2286 0.8769 0.183 Uiso 1 calc . .
C2 C 0.2922(13) 0.3493(9) 0.9793(6) 0.135(3) Uani 1 d . .
C3 C 0.1413(14) 0.3419(7) 0.9991(6) 0.126(3) Uani 1 d . .
H3 H 0.0935 0.3154 0.9547 0.151 Uiso 1 calc . .
C4 C 0.0582(10) 0.3808(7) 1.1003(6) 0.111(2) Uani 1 d . .
H4 H -0.0484 0.3834 1.1276 0.133 Uiso 1 calc . .
C5 C 0.1557(8) 0.4113(6) 1.1464(4) 0.0880(17) Uani 1 d . .
C6 C 0.1277(12) 0.4488(8) 1.2496(5) 0.132(3) Uani 1 d . .
H6A H 0.017 0.4539 1.281 0.158 Uiso 1 calc . .
H6B H 0.1911 0.3733 1.2813 0.158 Uiso 1 calc . .
C7 C 0.0525(7) 0.6987(7) 1.2437(5) 0.0953(18) Uani 1 d . .
H7A H -0.0517 0.7002 1.2856 0.114 Uiso 1 calc . .
H7B H 0.0456 0.6976 1.1769 0.114 Uiso 1 calc . .
C8 C 0.1055(6) 0.8253(6) 1.2600(5) 0.0807(16) Uani 1 d . .
C9 C 0.1005(7) 0.8592(7) 1.3532(5) 0.0984(19) Uani 1 d . .
H9 H 0.0598 0.8042 1.405 0.118 Uiso 1 calc . .
C10 C 0.1541(9) 0.9721(9) 1.3710(6) 0.115(2) Uani 1 d . .
H10 H 0.1492 0.9943 1.4342 0.138 Uiso 1 calc . .
C11 C 0.2147(9) 1.0515(7) 1.2945(8) 0.117(2) Uani 1 d . .
H11 H 0.2531 1.1272 1.3062 0.14 Uiso 1 calc . .
C12 C 0.2207(8) 1.0225(7) 1.2000(6) 0.105(2) Uani 1 d . .
H12 H 0.2607 1.0787 1.1489 0.126 Uiso 1 calc . .
C13 C 0.1663(7) 0.9085(7) 1.1830(5) 0.0870(17) Uani 1 d . .
C14 C 0.2440(9) 0.9358(8) 1.0069(5) 0.116(2) Uani 1 d . .
H14A H 0.3541 0.9289 1.0069 0.14 Uiso 1 calc . .
H14B H 0.1912 1.0349 1.0047 0.14 Uiso 1 calc . .
C15 C 0.2354(9) 0.8633(9) 0.9216(6) 0.130(3) Uani 1 d . .
H15A H 0.1247 0.874 0.9217 0.156 Uiso 1 calc . .
H15B H 0.282 0.7633 0.9275 0.156 Uiso 1 calc . .
C16 C 0.3185(14) 0.9180(11) 0.8271(6) 0.174(4) Uani 1 d . .
H16A H 0.4149 0.9369 0.837 0.209 Uiso 1 calc . .
H16B H 0.2516 1.0085 0.8147 0.209 Uiso 1 calc . .
C17 C 0.3685(14) 0.8299(13) 0.7285(11) 0.219(6) Uani 1 d . .
H17A H 0.4365 0.8743 0.6778 0.263 Uiso 1 calc . .
H17B H 0.4263 0.7344 0.7391 0.263 Uiso 1 calc . .
C18 C 0.2384(13) 0.8276(10) 0.7030(12) 0.220(7) Uani 1 d . .
H18A H 0.1889 0.9231 0.686 0.264 Uiso 1 calc . .
H18B H 0.1654 0.7971 0.7585 0.264 Uiso 1 calc . .
C19 C 0.2625(10) 0.7274(9) 0.6138(6) 0.131(3) Uani 1 d . .
H19A H 0.1621 0.7309 0.5982 0.157 Uiso 1 calc . .
H19B H 0.3353 0.7542 0.5566 0.157 Uiso 1 calc . .
C20 C 0.3248(7) 0.4718(9) 0.6039(5) 0.097(2) Uani 1 d . .
C21 C 0.2540(10) 0.4766(11) 0.5262(6) 0.131(3) Uani 1 d . .
H21 H 0.2114 0.5624 0.499 0.157 Uiso 1 calc . .
C22 C 0.2489(13) 0.3490(16) 0.4905(6) 0.156(4) Uani 1 d . .
H22 H 0.199 0.3489 0.4405 0.187 Uiso 1 calc . .
C23 C 0.3145(14) 0.2301(17) 0.5277(8) 0.167(5) Uani 1 d . .
H23 H 0.3123 0.1464 0.5017 0.2 Uiso 1 calc . .
C24 C 0.3842(9) 0.2220(9) 0.6008(7) 0.127(3) Uani 1 d . .
H24 H 0.4283 0.1344 0.6251 0.152 Uiso 1 calc . .
C25 C 0.3908(7) 0.3455(9) 0.6408(5) 0.099(2) Uani 1 d . .
C26 C 0.4734(11) 0.3418(11) 0.7202(6) 0.153(2) Uani 1 d . .
H26A H 0.5491 0.2519 0.721 0.183 Uiso 1 calc . .
H26B H 0.5308 0.4162 0.7097 0.183 Uiso 1 calc . .
O1 O 0.3582(6) 0.3612(7) 0.8097(4) 0.147(2) Uani 1 d . .
O2 O 0.1639(6) 0.5780(4) 1.2644(3) 0.1036(14) Uani 1 d . .
O3 O 0.1674(6) 0.8693(5) 1.0935(4) 0.1095(15) Uani 1 d . .
O4 O 0.3274(6) 0.5904(6) 0.6490(4) 0.1296(18) Uani 1 d . .
S1 S 0.3419(2) 0.3988(2) 1.07214(15) 0.1285(10) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C1 C2 1.544(11) . ?
C1 O1 1.257(8) . ?
C2 C3 1.327(12) . ?
C2 S1 1.638(10) . ?
C3 H3 0.93 . ?
C3 C4 1.478(12) . ?
C4 H4 0.93 . ?
C4 C5 1.314(9) . ?
C5 C6 1.489(9) . ?
C5 S1 1.716(6) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C6 O2 1.421(8) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C7 C8 1.483(8) . ?
C7 O2 1.410(7) . ?
C8 C9 1.381(9) . ?
C8 C13 1.393(8) . ?
C9 H9 0.93 . ?
C9 C10 1.370(9) . ?
C10 H10 0.93 . ?
C10 C11 1.365(10) . ?
C11 H11 0.93 . ?
C11 C12 1.383(10) . ?
C12 H12 0.93 . ?
C12 C13 1.380(9) . ?
C13 O3 1.357(7) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C14 C15 1.481(10) . ?
C14 O3 1.443(8) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C15 C16 1.494(11) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C16 C17 1.613(16) . ?
C17 H17A 0.97 . ?
C17 H17B 0.97 . ?
C17 C18 1.310(14) . ?
C18 H18A 0.97 . ?
C18 H18B 0.97 . ?
C18 C19 1.604(14) . ?
C19 H19A 0.97 . ?
C19 H19B 0.97 . ?
C19 O4 1.429(8) . ?
C20 C21 1.400(10) . ?
C20 C25 1.358(9) . ?
C20 O4 1.376(8) . ?
C21 H21 0.93 . ?
C21 C22 1.398(13) . ?
C22 H22 0.93 . ?
C22 C23 1.304(14) . ?
C23 H23 0.93 . ?
C23 C24 1.330(13) . ?
C24 H24 0.93 . ?
C24 C25 1.395(10) . ?
C25 C26 1.493(10) . ?
C26 H26A 0.97 . ?
C26 H26B 0.97 . ?
C26 O1 1.417(9) . ?

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
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109 . . ?
C2 C1 H1B 109 . . ?
O1 C1 H1A 109 . . ?
O1 C1 H1B 109 . . ?
O1 C1 C2 112.9(8) . . ?
C1 C2 S1 118.2(8) . . ?
C3 C2 C1 128.8(9) . . ?
C3 C2 S1 112.9(6) . . ?
C2 C3 H3 124.1 . . ?
C2 C3 C4 111.8(7) . . ?
C4 C3 H3 124.1 . . ?
C3 C4 H4 124.7 . . ?
C5 C4 C3 110.7(7) . . ?
C5 C4 H4 124.7 . . ?
C4 C5 C6 129.7(7) . . ?
C4 C5 S1 111.6(5) . . ?
C6 C5 S1 118.6(6) . . ?
C5 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
O2 C6 C5 115.2(5) . . ?
O2 C6 H6A 108.5 . . ?
O2 C6 H6B 108.5 . . ?
H7A C7 H7B 108.4 . . ?
C8 C7 H7A 110.1 . . ?
C8 C7 H7B 110.1 . . ?
O2 C7 H7A 110.1 . . ?
O2 C7 H7B 110.1 . . ?
O2 C7 C8 108.2(5) . . ?
C9 C8 C7 119.6(6) . . ?
C9 C8 C13 118.9(6) . . ?
C13 C8 C7 121.5(6) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.4(7) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 120.6 . . ?
C11 C10 C9 118.9(7) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 H11 119.1 . . ?
C10 C11 C12 121.8(7) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.8(7) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 C8 120.3(7) . . ?
O3 C13 C8 115.7(6) . . ?
O3 C13 C12 124.0(7) . . ?
H14A C14 H14B 108.4 . . ?
C15 C14 H14A 110 . . ?
C15 C14 H14B 110 . . ?
O3 C14 H14A 110 . . ?
O3 C14 H14B 110 . . ?
O3 C14 C15 108.4(6) . . ?
C14 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C14 C15 C16 113.6(8) . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C15 C16 H16A 106.8 . . ?
C15 C16 H16B 106.8 . . ?
C15 C16 C17 122.2(10) . . ?
H16A C16 H16B 106.6 . . ?
C17 C16 H16A 106.8 . . ?
C17 C16 H16B 106.8 . . ?
C16 C17 H17A 110.1 . . ?
C16 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?
C18 C17 C16 107.9(10) . . ?
C18 C17 H17A 110.1 . . ?
C18 C17 H17B 110.1 . . ?
C17 C18 H18A 108.5 . . ?
C17 C18 H18B 108.5 . . ?
C17 C18 C19 115.2(11) . . ?
H18A C18 H18B 107.5 . . ?
C19 C18 H18A 108.5 . . ?
C19 C18 H18B 108.5 . . ?
C18 C19 H19A 111.1 . . ?
C18 C19 H19B 111.1 . . ?
H19A C19 H19B 109.1 . . ?
O4 C19 C18 103.2(7) . . ?
O4 C19 H19A 111.1 . . ?
O4 C19 H19B 111.1 . . ?
C25 C20 C21 120.1(8) . . ?
C25 C20 O4 116.5(6) . . ?
O4 C20 C21 123.4(8) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 C20 118.3(9) . . ?
C22 C21 H21 120.9 . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.6(11) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 118.2 . . ?
C22 C23 C24 123.6(13) . . ?
C24 C23 H23 118.2 . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.6(10) . . ?
C25 C24 H24 120.2 . . ?
C20 C25 C24 118.8(8) . . ?
C20 C25 C26 119.5(8) . . ?
C24 C25 C26 121.6(9) . . ?
C25 C26 H26A 110 . . ?
C25 C26 H26B 110 . . ?
H26A C26 H26B 108.3 . . ?
O1 C26 C25 108.6(7) . . ?
O1 C26 H26A 110 . . ?
O1 C26 H26B 110 . . ?
C1 O1 C26 112.9(6) . . ?
C7 O2 C6 113.7(6) . . ?
C13 O3 C14 121.3(5) . . ?
C20 O4 C19 120.0(6) . . ?
C2 S1 C5 93.1(4) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 970711'
