# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

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

data_307_0m
_database_code_depnum_ccdc_archive 'CCDC 1453196'
_audit_update_record             
;
2016-02-13 deposited with the CCDC.	2019-03-20 downloaded from the CCDC.
;

_audit_creation_date             2016-02-08T13:24:18-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        307
_chemical_name_common            307
_chemical_formula_moiety         'C26 H24 O7'
_chemical_formula_sum            'C26 H24 O7'
_chemical_formula_weight         448.45

#----------------------------------------------------------------------------#
#                   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                   10.0326(6)
_cell_length_b                   10.6832(5)
_cell_length_c                   12.0430(7)
_cell_angle_alpha                114.722(3)
_cell_angle_beta                 97.632(4)
_cell_angle_gamma                108.601(4)
_cell_volume                     1056.76(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    38842
_cell_measurement_theta_min      3
_cell_measurement_theta_max      20

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

_exptl_crystal_description       piece
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_special_details           
;
 10 seconds, 0.5 degrees, 40 mm
;

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

_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_absorpt_correction_T_min  0.9918
_exptl_absorpt_correction_T_max  0.999

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0865
_diffrn_reflns_av_unetI/netI     0.0786
_diffrn_reflns_number            38842
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         28.65
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             5410
_reflns_number_gt                3120
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   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 > 2σ(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)+(0.0471P)²+0.2778P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5410
_refine_ls_number_parameters     303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1157
_refine_ls_R_factor_gt           0.052
_refine_ls_wR_factor_ref         0.1274
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.062

#----------------------------------------------------------------------------#
#                   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
C1 C -0.4984(2) 0.2137(2) 0.1233(2) 0.0272(5) Uani 1 1 d . . .
H1 H -0.5815 0.1394 0.1233 0.033 Uiso 1 1 calc R . .
C2 C -0.3719(2) 0.1898(2) 0.1125(2) 0.0249(5) Uani 1 1 d . . .
H2 H -0.3671 0.0998 0.1065 0.03 Uiso 1 1 calc R . .
C3 C -0.2523(2) 0.2976(2) 0.11041(19) 0.0210(5) Uani 1 1 d . . .
H3 H -0.1661 0.2803 0.102 0.025 Uiso 1 1 calc R . .
C4 C -0.2563(2) 0.4317(2) 0.12056(19) 0.0185(4) Uani 1 1 d . . .
C5 C -0.3845(2) 0.4540(2) 0.1324(2) 0.0216(5) Uani 1 1 d . . .
H5 H -0.3896 0.5441 0.1393 0.026 Uiso 1 1 calc R . .
C6 C -0.5036(2) 0.3468(2) 0.1342(2) 0.0239(5) Uani 1 1 d . . .
H6 H -0.5899 0.3639 0.143 0.029 Uiso 1 1 calc R . .
C7 C -0.1207(2) 0.5491(2) 0.12200(19) 0.0179(4) Uani 1 1 d . . .
H7 H -0.0606 0.4939 0.0834 0.021 Uiso 1 1 calc R . .
C8 C -0.1618(2) 0.6108(2) 0.03401(19) 0.0203(4) Uani 1 1 d . . .
H8A H -0.1942 0.5293 -0.0563 0.024 Uiso 1 1 calc R . .
H8B H -0.2476 0.6341 0.05 0.024 Uiso 1 1 calc R . .
C9 C -0.0427(2) 0.7491(2) 0.04857(19) 0.0196(4) Uani 1 1 d . . .
C10 C 0.0790(2) 0.8217(2) 0.14783(19) 0.0188(4) Uani 1 1 d . . .
C11 C 0.1197(2) 0.7771(2) 0.24532(19) 0.0190(4) Uani 1 1 d . . .
H11 H 0.1764 0.7149 0.2129 0.023 Uiso 1 1 calc R . .
C12 C -0.0191(2) 0.6765(2) 0.26218(18) 0.0161(4) Uani 1 1 d . . .
C13 C 0.2287(2) 0.9288(2) 0.35719(19) 0.0174(4) Uani 1 1 d . . .
C14 C 0.2998(2) 0.9791(2) 0.4829(2) 0.0196(4) Uani 1 1 d . . .
H14 H 0.2751 0.9126 0.5176 0.023 Uiso 1 1 calc R . .
C15 C 0.4092(2) 1.1282(2) 0.56123(19) 0.0187(4) Uani 1 1 d . . .
C16 C 0.4458(2) 1.2238(2) 0.5068(2) 0.0210(5) Uani 1 1 d . . .
C17 C 0.3743(2) 1.1755(2) 0.3793(2) 0.0221(5) Uani 1 1 d . . .
H17 H 0.3981 1.2404 0.3431 0.026 Uiso 1 1 calc R . .
C18 C 0.2676(2) 1.0291(2) 0.30859(19) 0.0192(4) Uani 1 1 d . . .
C19 C 0.4840(2) 1.1846(2) 0.6968(2) 0.0221(5) Uani 1 1 d . . .
C20 C 0.4425(2) 1.0887(2) 0.7582(2) 0.0263(5) Uani 1 1 d . . .
H20A H 0.5126 1.1397 0.8446 0.039 Uiso 1 1 calc R . .
H20B H 0.4452 0.9908 0.7062 0.039 Uiso 1 1 calc R . .
H20C H 0.3425 1.0723 0.7642 0.039 Uiso 1 1 calc R . .
C21 C -0.0773(2) 0.8039(2) -0.0421(2) 0.0232(5) Uani 1 1 d . . .
H21A H -0.149 0.8473 -0.021 0.035 Uiso 1 1 calc R . .
H21B H -0.1192 0.7189 -0.1303 0.035 Uiso 1 1 calc R . .
H21C H 0.0135 0.8815 -0.0347 0.035 Uiso 1 1 calc R . .
C22 C -0.0958(2) 0.7714(2) 0.33433(19) 0.0178(4) Uani 1 1 d . . .
C23 C 0.0400(2) 0.6047(2) 0.33119(19) 0.0183(4) Uani 1 1 d . . .
C24 C -0.0695(2) 0.6958(2) 0.4998(2) 0.0206(5) Uani 1 1 d . . .
C25 C -0.0015(2) 0.7925(2) 0.6434(2) 0.0252(5) Uani 1 1 d . . .
H25A H 0.027 0.7339 0.6788 0.038 Uiso 1 1 calc R . .
H25B H -0.0736 0.8243 0.6812 0.038 Uiso 1 1 calc R . .
H25C H 0.0862 0.8821 0.6638 0.038 Uiso 1 1 calc R . .
C26 C -0.2103(2) 0.5581(2) 0.4577(2) 0.0257(5) Uani 1 1 d . . .
H26A H -0.2429 0.4956 0.3639 0.039 Uiso 1 1 calc R . .
H26B H -0.2871 0.5903 0.4846 0.039 Uiso 1 1 calc R . .
H26C H -0.1922 0.4989 0.4972 0.039 Uiso 1 1 calc R . .
O1 O 0.18826(15) 0.96514(15) 0.18167(13) 0.0212(3) Uani 1 1 d . . .
O2 O 0.55077(17) 1.36733(16) 0.57519(15) 0.0300(4) Uani 1 1 d . . .
H2A H 0.5943 1.3829 0.6473 0.045 Uiso 1 1 calc R . .
O3 O 0.58229(16) 1.31592(16) 0.76301(14) 0.0296(4) Uani 1 1 d . . .
O4 O -0.09685(16) 0.79247(15) 0.45236(13) 0.0213(3) Uani 1 1 d . . .
O5 O 0.04113(16) 0.64830(15) 0.45351(13) 0.0227(3) Uani 1 1 d . . .
O6 O 0.09901(16) 0.52177(15) 0.28421(14) 0.0239(3) Uani 1 1 d . . .
O7 O -0.14900(16) 0.83492(15) 0.29266(13) 0.0226(3) Uani 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.385(3) . ?
C1 C6 1.392(3) . ?
C1 H1 0.95 . ?
C2 C3 1.385(3) . ?
C2 H2 0.95 . ?
C3 C4 1.400(3) . ?
C3 H3 0.95 . ?
C4 C5 1.395(3) . ?
C4 C7 1.520(3) . ?
C5 C6 1.376(3) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.539(3) . ?
C7 C12 1.574(3) . ?
C7 H7 1 . ?
C8 C9 1.498(3) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.324(3) . ?
C9 C21 1.490(3) . ?
C10 O1 1.416(2) . ?
C10 C11 1.495(3) . ?
C11 C13 1.513(3) . ?
C11 C12 1.562(3) . ?
C11 H11 1 . ?
C12 C22 1.521(3) . ?
C12 C23 1.524(3) . ?
C13 C14 1.371(3) . ?
C13 C18 1.400(3) . ?
C14 C15 1.409(3) . ?
C14 H14 0.95 . ?
C15 C16 1.412(3) . ?
C15 C19 1.468(3) . ?
C16 O2 1.350(2) . ?
C16 C17 1.395(3) . ?
C17 C18 1.376(3) . ?
C17 H17 0.95 . ?
C18 O1 1.376(2) . ?
C19 O3 1.245(2) . ?
C19 C20 1.488(3) . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C22 O7 1.201(2) . ?
C22 O4 1.345(2) . ?
C23 O6 1.209(2) . ?
C23 O5 1.344(2) . ?
C24 O5 1.445(2) . ?
C24 O4 1.450(2) . ?
C24 C25 1.505(3) . ?
C24 C26 1.509(3) . ?
C25 H25A 0.98 . ?
C25 H25B 0.98 . ?
C25 H25C 0.98 . ?
C26 H26A 0.98 . ?
C26 H26B 0.98 . ?
C26 H26C 0.98 . ?
O2 H2A 0.84 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.8(2) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C3 C2 C1 119.64(19) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 121.14(19) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.28(19) . . ?
C5 C4 C7 122.38(17) . . ?
C3 C4 C7 119.32(18) . . ?
C6 C5 C4 120.69(19) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C4 C7 C8 111.82(16) . . ?
C4 C7 C12 112.66(16) . . ?
C8 C7 C12 113.71(15) . . ?
C4 C7 H7 106 . . ?
C8 C7 H7 106 . . ?
C12 C7 H7 106 . . ?
C9 C8 C7 116.34(17) . . ?
C9 C8 H8A 108.2 . . ?
C7 C8 H8A 108.2 . . ?
C9 C8 H8B 108.2 . . ?
C7 C8 H8B 108.2 . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 C21 124.71(19) . . ?
C10 C9 C8 117.95(18) . . ?
C21 C9 C8 116.99(18) . . ?
C9 C10 O1 122.51(18) . . ?
C9 C10 C11 128.01(18) . . ?
O1 C10 C11 109.33(17) . . ?
C10 C11 C13 101.22(15) . . ?
C10 C11 C12 112.24(16) . . ?
C13 C11 C12 120.77(16) . . ?
C10 C11 H11 107.3 . . ?
C13 C11 H11 107.3 . . ?
C12 C11 H11 107.3 . . ?
C22 C12 C23 114.17(16) . . ?
C22 C12 C11 110.46(15) . . ?
C23 C12 C11 104.75(15) . . ?
C22 C12 C7 112.38(16) . . ?
C23 C12 C7 108.95(14) . . ?
C11 C12 C7 105.52(15) . . ?
C14 C13 C18 118.43(18) . . ?
C14 C13 C11 134.63(18) . . ?
C18 C13 C11 106.67(17) . . ?
C13 C14 C15 120.64(19) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 118.58(19) . . ?
C14 C15 C19 121.26(18) . . ?
C16 C15 C19 120.16(18) . . ?
O2 C16 C17 116.22(18) . . ?
O2 C16 C15 122.00(19) . . ?
C17 C16 C15 121.78(18) . . ?
C18 C17 C16 116.63(19) . . ?
C18 C17 H17 121.7 . . ?
C16 C17 H17 121.7 . . ?
C17 C18 O1 123.36(18) . . ?
C17 C18 C13 123.93(19) . . ?
O1 C18 C13 112.71(17) . . ?
O3 C19 C15 119.87(19) . . ?
O3 C19 C20 118.88(19) . . ?
C15 C19 C20 121.24(18) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 C21 H21A 109.5 . . ?
C9 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C9 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O7 C22 O4 118.49(17) . . ?
O7 C22 C12 122.39(18) . . ?
O4 C22 C12 119.01(16) . . ?
O6 C23 O5 118.82(18) . . ?
O6 C23 C12 122.10(18) . . ?
O5 C23 C12 118.66(16) . . ?
O5 C24 O4 110.59(15) . . ?
O5 C24 C25 105.58(16) . . ?
O4 C24 C25 106.74(15) . . ?
O5 C24 C26 109.47(16) . . ?
O4 C24 C26 110.42(17) . . ?
C25 C24 C26 113.92(18) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C18 O1 C10 106.49(15) . . ?
C16 O2 H2A 109.5 . . ?
C22 O4 C24 123.03(14) . . ?
C23 O5 C24 121.12(15) . . ?


# END of CIF
