# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_Maayan17
_audit_block_doi                 10.5517/cc140b4m
_database_code_depnum_ccdc_archive 'CCDC 1042999'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.tet.2016.03.065 2016
2 10.1039/C5DT04171F 2016
_audit_update_record             
;
2016-01-14 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;

_chemical_name_systematic        
'(4S,12S,18R,26R)-4,12,18,26-Tetrahydroxy-13.17-dioxaheptacyclo[14.10.0.03,14.04,12.06,11.018,26.019,24] hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione'
_chemical_name_common            'Bis Ninhydrin Resorcinol-"boat" configuration'
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H14 O8'
_chemical_formula_sum            'C24 H14 O8'
_chemical_formula_weight         430.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5394(6)
_cell_length_b                   10.6149(9)
_cell_length_c                   12.1610(10)
_cell_angle_alpha                84.0000(10)
_cell_angle_beta                 75.3820(10)
_cell_angle_gamma                86.891(2)
_cell_volume                     936.19(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(1)
_cell_measurement_reflns_used    3126
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      28.01

_exptl_crystal_description       shapeless
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10887
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         28.01
_reflns_number_total             4339
_reflns_number_gt                3731
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0533P)²+0.5653P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4339
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1277
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.9442(3) 0.16916(18) 0.65657(17) 0.0156(4) Uani 1 1 d . . .
C2 C 1.0250(3) 0.25100(19) 0.56313(17) 0.0175(4) Uani 1 1 d . . .
H2 H 1.1259 0.3014 0.5620 0.021 Uiso 1 1 calc R . .
C3 C 0.9463(3) 0.25336(18) 0.47119(16) 0.0152(4) Uani 1 1 d . . .
C4 C 0.7986(3) 0.18004(18) 0.47142(17) 0.0163(4) Uani 1 1 d . . .
C5 C 0.7199(3) 0.09956(18) 0.56621(17) 0.0172(4) Uani 1 1 d . . .
H5 H 0.6192 0.0491 0.5671 0.021 Uiso 1 1 calc R . .
C6 C 0.7941(3) 0.09579(18) 0.65964(17) 0.0159(4) Uani 1 1 d . . .
C7 C 0.8671(3) 0.07637(19) 0.83971(17) 0.0167(4) Uani 1 1 d . . .
C8 C 0.7408(3) 0.16439(19) 0.91593(16) 0.0177(4) Uani 1 1 d . . .
C9 C 0.7886(3) 0.2529(2) 0.97872(18) 0.0237(5) Uani 1 1 d . . .
H9 H 0.9127 0.2615 0.9803 0.028 Uiso 1 1 calc R . .
C10 C 0.6494(3) 0.3285(2) 1.03940(19) 0.0282(5) Uani 1 1 d . . .
H10 H 0.6792 0.3905 1.0823 0.034 Uiso 1 1 calc R . .
C11 C 0.4673(3) 0.3151(2) 1.03850(19) 0.0287(5) Uani 1 1 d . . .
H11 H 0.3748 0.3678 1.0810 0.034 Uiso 1 1 calc R . .
C12 C 0.4190(3) 0.2265(2) 0.97678(18) 0.0245(5) Uani 1 1 d . . .
H12 H 0.2946 0.2166 0.9768 0.029 Uiso 1 1 calc R . .
C13 C 0.5587(3) 0.15189(19) 0.91442(17) 0.0185(4) Uani 1 1 d . . .
C14 C 0.5458(3) 0.05562(19) 0.83865(17) 0.0185(4) Uani 1 1 d . . .
C15 C 0.7415(3) 0.01939(18) 0.77371(16) 0.0161(4) Uani 1 1 d . . .
C16 C 0.8853(3) 0.31379(19) 0.29829(16) 0.0172(4) Uani 1 1 d . . .
C17 C 0.7557(3) 0.42719(19) 0.30260(16) 0.0171(4) Uani 1 1 d . . .
C18 C 0.7985(3) 0.5537(2) 0.27321(18) 0.0222(4) Uani 1 1 d . . .
H18 H 0.9224 0.5786 0.2472 0.027 Uiso 1 1 calc R . .
C19 C 0.6554(3) 0.6428(2) 0.2829(2) 0.0259(5) Uani 1 1 d . . .
H19 H 0.6817 0.7300 0.2641 0.031 Uiso 1 1 calc R . .
C20 C 0.4729(3) 0.6063(2) 0.3199(2) 0.0281(5) Uani 1 1 d . . .
H20 H 0.3773 0.6692 0.3255 0.034 Uiso 1 1 calc R . .
C21 C 0.4295(3) 0.4811(2) 0.34821(19) 0.0239(5) Uani 1 1 d . . .
H21 H 0.3054 0.4562 0.3724 0.029 Uiso 1 1 calc R . .
C22 C 0.5734(3) 0.39185(19) 0.34023(17) 0.0177(4) Uani 1 1 d . . .
C23 C 0.5644(3) 0.25348(19) 0.36188(16) 0.0159(4) Uani 1 1 d . . .
C24 C 0.7587(3) 0.19966(18) 0.35604(17) 0.0160(4) Uani 1 1 d . . .
O1 O 1.00159(18) 0.15344(13) 0.75497(11) 0.0171(3) Uani 1 1 d . . .
O2 O 0.9568(2) -0.01404(14) 0.89712(14) 0.0204(3) Uani 1 1 d . . .
H2OA H 1.025(7) -0.057(5) 0.846(5) 0.031 Uiso 0.50 1 d P . .
H2OB H 0.968(7) 0.006(5) 0.957(4) 0.031 Uiso 0.50 1 d P . .
O3 O 0.4074(2) 0.01243(16) 0.82597(14) 0.0283(4) Uani 1 1 d . . .
O4 O 0.7708(2) -0.11241(13) 0.76941(13) 0.0198(3) Uani 1 1 d . . .
H4O H 0.722(3) -0.138(2) 0.718(2) 0.030 Uiso 1 1 d . . .
O5 O 1.00984(18) 0.32671(13) 0.37109(11) 0.0185(3) Uani 1 1 d . . .
O6 O 0.9879(2) 0.30269(15) 0.18858(12) 0.0219(3) Uani 1 1 d . . .
H6O H 1.054(4) 0.232(3) 0.193(2) 0.033 Uiso 1 1 d . . .
O7 O 0.43090(19) 0.18853(14) 0.37802(13) 0.0227(3) Uani 1 1 d . . .
O8 O 0.7957(2) 0.08845(15) 0.30073(15) 0.0276(4) Uani 1 1 d . . .
H8O H 0.721(4) 0.078(3) 0.268(3) 0.041 Uiso 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 O1 1.363(2) . ?
C1 C2 1.385(3) . ?
C1 C6 1.399(3) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 O5 1.366(2) . ?
C3 C4 1.392(3) . ?
C4 C5 1.384(3) . ?
C4 C24 1.499(3) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 C15 1.504(3) . ?
C7 O2 1.376(2) . ?
C7 O1 1.465(2) . ?
C7 C8 1.509(3) . ?
C7 C15 1.566(3) . ?
C8 C9 1.386(3) . ?
C8 C13 1.391(3) . ?
C9 C10 1.390(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.468(3) . ?
C14 O3 1.213(2) . ?
C14 C15 1.537(3) . ?
C15 O4 1.409(2) . ?
C16 O6 1.376(2) . ?
C16 O5 1.464(2) . ?
C16 C17 1.505(3) . ?
C16 C24 1.575(3) . ?
C17 C18 1.387(3) . ?
C17 C22 1.393(3) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.397(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.374(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.393(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.467(3) . ?
C23 O7 1.214(2) . ?
C23 C24 1.530(3) . ?
C24 O8 1.400(2) . ?
O2 H2OA 0.86(6) . ?
O2 H2OB 0.81(5) . ?
O4 H4O 0.88(3) . ?
O6 H6O 0.88(3) . ?
O8 H8O 0.79(3) . ?

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 123.35(17) . . ?
O1 C1 C6 113.45(17) . . ?
C2 C1 C6 123.20(18) . . ?
C1 C2 C3 114.49(18) . . ?
C1 C2 H2 122.8 . . ?
C3 C2 H2 122.8 . . ?
O5 C3 C2 122.68(17) . . ?
O5 C3 C4 113.85(17) . . ?
C2 C3 C4 123.46(18) . . ?
C5 C4 C3 120.85(18) . . ?
C5 C4 C24 130.10(18) . . ?
C3 C4 C24 108.94(17) . . ?
C4 C5 C6 117.13(18) . . ?
C4 C5 H5 121.4 . . ?
C6 C5 H5 121.4 . . ?
C5 C6 C1 120.86(18) . . ?
C5 C6 C15 130.21(18) . . ?
C1 C6 C15 108.92(17) . . ?
O2 C7 O1 109.58(15) . . ?
O2 C7 C8 113.97(17) . . ?
O1 C7 C8 108.01(15) . . ?
O2 C7 C15 113.53(16) . . ?
O1 C7 C15 106.87(15) . . ?
C8 C7 C15 104.47(15) . . ?
C9 C8 C13 120.72(19) . . ?
C9 C8 C7 127.67(19) . . ?
C13 C8 C7 111.56(17) . . ?
C8 C9 C10 117.9(2) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 H9 121.0 . . ?
C9 C10 C11 121.2(2) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 117.9(2) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
C8 C13 C12 121.22(19) . . ?
C8 C13 C14 109.95(18) . . ?
C12 C13 C14 128.81(19) . . ?
O3 C14 C13 127.32(19) . . ?
O3 C14 C15 124.73(19) . . ?
C13 C14 C15 107.94(16) . . ?
O4 C15 C6 114.52(16) . . ?
O4 C15 C14 112.88(16) . . ?
C6 C15 C14 110.73(16) . . ?
O4 C15 C7 112.18(16) . . ?
C6 C15 C7 101.36(15) . . ?
C14 C15 C7 104.11(15) . . ?
O6 C16 O5 108.66(15) . . ?
O6 C16 C17 110.93(16) . . ?
O5 C16 C17 109.77(15) . . ?
O6 C16 C24 116.24(16) . . ?
O5 C16 C24 106.58(15) . . ?
C17 C16 C24 104.44(15) . . ?
C18 C17 C22 120.40(19) . . ?
C18 C17 C16 128.06(18) . . ?
C22 C17 C16 111.53(17) . . ?
C19 C18 C17 118.1(2) . . ?
C19 C18 H18 121.0 . . ?
C17 C18 H18 121.0 . . ?
C18 C19 C20 121.1(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 121.1(2) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 117.7(2) . . ?
C20 C21 H21 121.1 . . ?
C22 C21 H21 121.1 . . ?
C21 C22 C17 121.52(19) . . ?
C21 C22 C23 128.50(19) . . ?
C17 C22 C23 109.91(18) . . ?
O7 C23 C22 127.97(19) . . ?
O7 C23 C24 123.81(18) . . ?
C22 C23 C24 108.17(16) . . ?
O8 C24 C4 110.85(16) . . ?
O8 C24 C23 112.62(16) . . ?
C4 C24 C23 112.16(16) . . ?
O8 C24 C16 115.35(16) . . ?
C4 C24 C16 101.33(15) . . ?
C23 C24 C16 103.89(15) . . ?
C1 O1 C7 107.68(14) . . ?
C7 O2 H2OA 106(3) . . ?
C7 O2 H2OB 113(4) . . ?
H2OA O2 H2OB 133(5) . . ?
C15 O4 H4O 110.2(17) . . ?
C3 O5 C16 107.59(14) . . ?
C16 O6 H6O 105.3(17) . . ?
C24 O8 H8O 112(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O8 H8O O3 0.79(3) 2.01(3) 2.753(2) 157(3) 2_656
O6 H6O O4 0.88(3) 1.89(3) 2.740(2) 161(2) 2_756
O4 H4O O7 0.88(3) 1.96(3) 2.827(2) 169(2) 2_656
O2 H2OA O8 0.86(6) 1.99(6) 2.805(2) 157(5) 2_756
O2 H2OB O2 0.81(5) 2.00(5) 2.789(3) 164(5) 2_757

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        28.01
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_Maayan33
_audit_block_doi                 10.5517/cc140b5n
_database_code_depnum_ccdc_archive 'CCDC 1043000'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.tet.2016.03.065 2016
2 10.1039/C5DT04171F 2016
_audit_update_record             
;
2016-01-14 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'(4S,12S,18S,26S)-4,12,18,26-Tetrahydroxy-13.17-dioxaheptacyclo[14.10.0.03,14.04,12.06,11.018,26.019,24] hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione'
_chemical_name_common            
'Bis Ninhydrin Resorcinol "chair" configuration'
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H14 O8, C2 H6 O'
_chemical_formula_sum            'C26 H20 O9'
_chemical_formula_weight         476.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'
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                   10.811(1)
_cell_length_b                   7.8640(8)
_cell_length_c                   26.025(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.560(2)
_cell_angle_gamma                90.00
_cell_volume                     2181.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(1)
_cell_measurement_reflns_used    4887
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      26.77

_exptl_crystal_description       shapeless
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22086
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         26.50
_reflns_number_total             4507
_reflns_number_gt                4126
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0431P)²+5.3857P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4507
_refine_ls_number_parameters     321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0977
_refine_ls_wR_factor_ref         0.1835
_refine_ls_wR_factor_gt          0.1792
_refine_ls_goodness_of_fit_ref   1.310
_refine_ls_restrained_S_all      1.310
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.5942(3) 0.6038(4) 0.19818(13) 0.0145(7) Uani 1 1 d . . .
H1 H 0.5731 0.6378 0.2307 0.017 Uiso 1 1 calc R . .
C2 C 0.6729(3) 0.6968(4) 0.17239(13) 0.0148(7) Uani 1 1 d . . .
C3 C 0.7059(3) 0.6493(4) 0.12482(13) 0.0152(7) Uani 1 1 d . . .
C4 C 0.6539(3) 0.5050(4) 0.09906(13) 0.0134(7) Uani 1 1 d . . .
H4A H 0.6732 0.4731 0.0661 0.016 Uiso 1 1 calc R . .
C5 C 0.5727(3) 0.4095(4) 0.12350(12) 0.0124(7) Uani 1 1 d . . .
C6 C 0.5483(3) 0.4562(4) 0.17258(13) 0.0140(7) Uani 1 1 d . . .
C7 C 0.8214(3) 0.8943(4) 0.15921(13) 0.0146(7) Uani 1 1 d . . .
C8 C 0.9512(3) 0.8446(4) 0.18616(13) 0.0156(7) Uani 1 1 d . . .
C9 C 1.0129(3) 0.8949(5) 0.23499(14) 0.0211(8) Uani 1 1 d . . .
H9 H 0.9728 0.9658 0.2568 0.025 Uiso 1 1 calc R . .
C10 C 1.1344(4) 0.8383(5) 0.25074(15) 0.0260(9) Uani 1 1 d . . .
H10 H 1.1778 0.8706 0.2841 0.031 Uiso 1 1 calc R . .
C11 C 1.1948(4) 0.7353(5) 0.21914(16) 0.0282(9) Uani 1 1 d . . .
H11 H 1.2790 0.7009 0.2309 0.034 Uiso 1 1 calc R . .
C12 C 1.1337(3) 0.6826(5) 0.17087(16) 0.0251(9) Uani 1 1 d . . .
H12 H 1.1741 0.6118 0.1492 0.030 Uiso 1 1 calc R . .
C13 C 1.0095(3) 0.7377(4) 0.15509(14) 0.0175(7) Uani 1 1 d . . .
C14 C 0.9246(3) 0.7004(4) 0.10588(14) 0.0161(7) Uani 1 1 d . . .
C15 C 0.7965(3) 0.7779(4) 0.10958(13) 0.0139(7) Uani 1 1 d . . .
C16 C 0.4407(3) 0.2045(4) 0.15549(13) 0.0155(7) Uani 1 1 d . . .
C17 C 0.3022(3) 0.2195(4) 0.13654(13) 0.0158(7) Uani 1 1 d . . .
C18 C 0.2066(3) 0.1969(5) 0.16546(15) 0.0202(8) Uani 1 1 d . . .
H18 H 0.2244 0.1694 0.2015 0.024 Uiso 1 1 calc R . .
C19 C 0.0846(4) 0.2158(5) 0.13998(16) 0.0255(9) Uani 1 1 d . . .
H19 H 0.0176 0.2012 0.1590 0.031 Uiso 1 1 calc R . .
C20 C 0.0573(3) 0.2555(5) 0.08729(16) 0.0262(9) Uani 1 1 d . . .
H20 H -0.0277 0.2651 0.0709 0.031 Uiso 1 1 calc R . .
C21 C 0.1522(3) 0.2813(5) 0.05836(15) 0.0235(8) Uani 1 1 d . . .
H21 H 0.1341 0.3108 0.0225 0.028 Uiso 1 1 calc R . .
C22 C 0.2760(3) 0.2621(4) 0.08404(13) 0.0154(7) Uani 1 1 d . . .
C23 C 0.3926(3) 0.2751(4) 0.06236(13) 0.0140(7) Uani 1 1 d . . .
C24 C 0.5044(3) 0.2478(4) 0.10696(12) 0.0123(7) Uani 1 1 d . . .
O1 O 0.7268(2) 0.8473(3) 0.19175(9) 0.0174(5) Uani 1 1 d . . .
O2 O 0.8146(2) 1.0663(3) 0.15067(10) 0.0184(5) Uani 1 1 d . . .
H2 H 0.7472 1.0897 0.1309 0.028 Uiso 1 1 calc R . .
O3 O 0.9474(2) 0.6233(3) 0.06820(10) 0.0245(6) Uani 1 1 d . . .
O4 O 0.7506(2) 0.8755(3) 0.06481(9) 0.0174(5) Uani 1 1 d . . .
H4 H 0.7192 0.8105 0.0405 0.026 Uiso 1 1 calc R . .
O5 O 0.4779(2) 0.3386(3) 0.19398(9) 0.0189(6) Uani 1 1 d . . .
O6 O 0.4717(2) 0.0491(3) 0.17839(10) 0.0217(6) Uani 1 1 d . . .
H6 H 0.5484 0.0302 0.1790 0.033 Uiso 1 1 calc R . .
O7 O 0.4042(2) 0.2989(3) 0.01731(9) 0.0203(6) Uani 1 1 d . . .
O8 O 0.5869(2) 0.1239(3) 0.09365(10) 0.0187(5) Uani 1 1 d . . .
H8 H 0.5455 0.0419 0.0789 0.028 Uiso 1 1 calc R . .
O9 O 0.4377(3) -0.1127(4) 0.04435(12) 0.0347(7) Uani 1 1 d . . .
H9O H 0.4636 -0.1701 0.0212 0.052 Uiso 1 1 d R . .
C25 C 0.3468(4) -0.2139(6) 0.06501(19) 0.0381(11) Uani 1 1 d . . .
H25A H 0.3288 -0.1606 0.0974 0.046 Uiso 1 1 calc R . .
H25B H 0.3824 -0.3282 0.0740 0.046 Uiso 1 1 calc R . .
C26 C 0.2285(5) -0.2317(8) 0.0277(2) 0.0519(14) Uani 1 1 d . . .
H26A H 0.1950 -0.1186 0.0175 0.078 Uiso 1 1 calc R . .
H26B H 0.1674 -0.2949 0.0441 0.078 Uiso 1 1 calc R . .
H26C H 0.2447 -0.2933 -0.0032 0.078 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
C1 C2 1.378(5) . ?
C1 C6 1.389(5) . ?
C1 H1 0.9500 . ?
C2 O1 1.377(4) . ?
C2 C3 1.395(5) . ?
C3 C4 1.388(5) . ?
C3 C15 1.506(5) . ?
C4 C5 1.388(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.396(5) . ?
C5 C24 1.497(5) . ?
C6 O5 1.373(4) . ?
C7 O2 1.371(4) . ?
C7 O1 1.479(4) . ?
C7 C8 1.513(5) . ?
C7 C15 1.569(5) . ?
C8 C13 1.388(5) . ?
C8 C9 1.391(5) . ?
C9 C10 1.383(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.405(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.476(5) . ?
C14 O3 1.213(4) . ?
C14 C15 1.531(5) . ?
C15 O4 1.415(4) . ?
C16 O6 1.376(4) . ?
C16 O5 1.464(4) . ?
C16 C17 1.501(5) . ?
C16 C24 1.573(4) . ?
C17 C18 1.387(5) . ?
C17 C22 1.389(5) . ?
C18 C19 1.383(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.401(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.468(5) . ?
C23 O7 1.214(4) . ?
C23 C24 1.545(4) . ?
C24 O8 1.403(4) . ?
O2 H2 0.8400 . ?
O4 H4 0.8400 . ?
O6 H6 0.8400 . ?
O8 H8 0.8400 . ?
O9 C25 1.437(5) . ?
O9 H9O 0.8385 . ?
C25 C26 1.479(7) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 114.2(3) . . ?
C2 C1 H1 122.9 . . ?
C6 C1 H1 122.9 . . ?
O1 C2 C1 122.4(3) . . ?
O1 C2 C3 113.6(3) . . ?
C1 C2 C3 124.0(3) . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 C15 130.6(3) . . ?
C2 C3 C15 109.1(3) . . ?
C3 C4 C5 117.2(3) . . ?
C3 C4 H4A 121.4 . . ?
C5 C4 H4A 121.4 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 C24 130.4(3) . . ?
C6 C5 C24 109.1(3) . . ?
O5 C6 C1 123.1(3) . . ?
O5 C6 C5 113.3(3) . . ?
C1 C6 C5 123.5(3) . . ?
O2 C7 O1 108.4(3) . . ?
O2 C7 C8 110.5(3) . . ?
O1 C7 C8 110.3(3) . . ?
O2 C7 C15 116.4(3) . . ?
O1 C7 C15 106.6(2) . . ?
C8 C7 C15 104.5(3) . . ?
C13 C8 C9 120.6(3) . . ?
C13 C8 C7 111.2(3) . . ?
C9 C8 C7 128.1(3) . . ?
C10 C9 C8 117.8(4) . . ?
C10 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
C9 C10 C11 121.9(4) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 120.7(4) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 117.6(4) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 H12 121.2 . . ?
C8 C13 C12 121.4(3) . . ?
C8 C13 C14 110.4(3) . . ?
C12 C13 C14 128.2(3) . . ?
O3 C14 C13 128.3(3) . . ?
O3 C14 C15 123.9(3) . . ?
C13 C14 C15 107.8(3) . . ?
O4 C15 C3 115.3(3) . . ?
O4 C15 C14 111.2(3) . . ?
C3 C15 C14 112.6(3) . . ?
O4 C15 C7 110.5(3) . . ?
C3 C15 C7 101.9(3) . . ?
C14 C15 C7 104.5(3) . . ?
O6 C16 O5 108.9(3) . . ?
O6 C16 C17 111.7(3) . . ?
O5 C16 C17 108.3(3) . . ?
O6 C16 C24 115.7(3) . . ?
O5 C16 C24 106.6(2) . . ?
C17 C16 C24 105.3(3) . . ?
C18 C17 C22 121.0(3) . . ?
C18 C17 C16 127.2(3) . . ?
C22 C17 C16 111.8(3) . . ?
C19 C18 C17 117.6(3) . . ?
C19 C18 H18 121.2 . . ?
C17 C18 H18 121.2 . . ?
C18 C19 C20 121.8(3) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C21 C20 C19 121.0(3) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C22 117.4(3) . . ?
C20 C21 H21 121.3 . . ?
C22 C21 H21 121.3 . . ?
C17 C22 C21 121.2(3) . . ?
C17 C22 C23 110.3(3) . . ?
C21 C22 C23 128.5(3) . . ?
O7 C23 C22 127.9(3) . . ?
O7 C23 C24 123.6(3) . . ?
C22 C23 C24 108.4(3) . . ?
O8 C24 C5 110.9(3) . . ?
O8 C24 C23 111.1(3) . . ?
C5 C24 C23 112.7(3) . . ?
O8 C24 C16 115.4(3) . . ?
C5 C24 C16 102.4(3) . . ?
C23 C24 C16 104.0(3) . . ?
C2 O1 C7 107.2(2) . . ?
C7 O2 H2 109.5 . . ?
C15 O4 H4 109.5 . . ?
C6 O5 C16 108.4(2) . . ?
C16 O6 H6 109.5 . . ?
C24 O8 H8 109.5 . . ?
C25 O9 H8 127.5 . . ?
C25 O9 H9O 107.6 . . ?
H8 O9 H9O 117.0 . . ?
O9 C25 C26 112.2(4) . . ?
O9 C25 H25A 109.2 . . ?
C26 C25 H25A 109.2 . . ?
O9 C25 H25B 109.2 . . ?
C26 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O8 H8 O9 0.84 1.82 2.649(4) 171.6 .
O6 H6 O1 0.84 2.38 3.151(3) 151.9 1_545
O2 H2 O8 0.84 1.86 2.693(3) 171.8 1_565
O4 H4 O7 0.84 2.03 2.839(3) 161.8 3_665
O9 H9O O7 0.84 2.13 2.925(4) 157.5 3_655

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.077
####################################################################### 
# 
# 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_maayan23
_audit_block_doi                 10.5517/cc140b6p
_database_code_depnum_ccdc_archive 'CCDC 1043001'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5DT04171F 2016
_audit_update_record             
;
2016-01-14 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Cesium Fluoride complex of Vasarene [4]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H14 Cs F O8, C2 H6 O'
_chemical_formula_sum            'C26 H20 Cs F O9'
_chemical_formula_weight         628.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cs Cs -0.3680 2.1192 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.2617(9)
_cell_length_b                   15.379(1)
_cell_length_c                   25.646(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4836.1(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(1)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      27.98

_exptl_crystal_description       shapeless
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2496
_exptl_absorpt_coefficient_mu    1.594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5901
_exptl_absorpt_correction_T_max  0.7206
_exptl_absorpt_process_details   'Bruker SADABS V2.05'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            52953
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         28.02
_reflns_number_total             5816
_reflns_number_gt                5508
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0310P)²+5.0655P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5816
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0644
_refine_ls_wR_factor_gt          0.0635
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.37568(14) 0.48902(11) 0.34766(7) 0.0170(3) Uani 1 1 d . . .
C2 C 0.26298(14) 0.48167(11) 0.34869(7) 0.0179(3) Uani 1 1 d . . .
H2 H 0.2260 0.4275 0.3466 0.022 Uiso 1 1 calc R . .
C3 C 0.20918(14) 0.56078(11) 0.35312(7) 0.0160(3) Uani 1 1 d . . .
C4 C 0.26272(14) 0.64047(11) 0.35813(7) 0.0152(3) Uani 1 1 d . . .
C5 C 0.37570(14) 0.64548(11) 0.35530(6) 0.0157(3) Uani 1 1 d . . .
H5 H 0.4128 0.6996 0.3576 0.019 Uiso 1 1 calc R . .
C6 C 0.43185(13) 0.56784(11) 0.34892(7) 0.0154(3) Uani 1 1 d . . .
C7 C 0.55725(14) 0.44938(11) 0.34953(7) 0.0178(3) Uani 1 1 d . . .
C8 C 0.59450(14) 0.43948(11) 0.40528(7) 0.0202(3) Uani 1 1 d . . .
C9 C 0.59915(17) 0.36359(13) 0.43469(9) 0.0298(4) Uani 1 1 d . . .
H9 H 0.5790 0.3091 0.4201 0.036 Uiso 1 1 calc R . .
C10 C 0.63408(19) 0.37012(15) 0.48587(10) 0.0369(5) Uani 1 1 d . . .
H10 H 0.6374 0.3191 0.5067 0.044 Uiso 1 1 calc R . .
C11 C 0.66444(19) 0.44917(16) 0.50759(9) 0.0363(5) Uani 1 1 d . . .
H11 H 0.6870 0.4515 0.5430 0.044 Uiso 1 1 calc R . .
C12 C 0.66220(17) 0.52500(14) 0.47816(8) 0.0279(4) Uani 1 1 d . . .
H12 H 0.6841 0.5792 0.4926 0.033 Uiso 1 1 calc R . .
C13 C 0.62666(14) 0.51858(12) 0.42676(7) 0.0203(3) Uani 1 1 d . . .
C14 C 0.61762(14) 0.58755(11) 0.38698(7) 0.0173(3) Uani 1 1 d . . .
C15 C 0.55204(13) 0.55051(11) 0.34124(7) 0.0157(3) Uani 1 1 d . . .
C16 C 0.07077(14) 0.65592(11) 0.36964(7) 0.0173(3) Uani 1 1 d . . .
C17 C 0.04406(15) 0.65471(11) 0.42717(7) 0.0202(3) Uani 1 1 d . . .
C18 C -0.03776(17) 0.60730(14) 0.45172(9) 0.0291(4) Uani 1 1 d . . .
H18 H -0.0842 0.5696 0.4325 0.035 Uiso 1 1 calc R . .
C19 C -0.0490(2) 0.61695(15) 0.50518(9) 0.0368(5) Uani 1 1 d . . .
H19 H -0.1043 0.5854 0.5230 0.044 Uiso 1 1 calc R . .
C20 C 0.0193(2) 0.67215(15) 0.53325(8) 0.0376(5) Uani 1 1 d . . .
H20 H 0.0090 0.6781 0.5698 0.045 Uiso 1 1 calc R . .
C21 C 0.1017(2) 0.71850(14) 0.50919(8) 0.0304(4) Uani 1 1 d . . .
H21 H 0.1489 0.7554 0.5285 0.037 Uiso 1 1 calc R . .
C22 C 0.11282(16) 0.70892(12) 0.45523(7) 0.0217(4) Uani 1 1 d . . .
C23 C 0.19029(15) 0.75269(12) 0.42015(7) 0.0194(3) Uani 1 1 d . . .
C24 C 0.17893(14) 0.71044(11) 0.36577(7) 0.0157(3) Uani 1 1 d . . .
Cs1 Cs 0.268898(9) 0.723940(8) 0.216390(5) 0.02347(5) Uani 1 1 d . . .
F1 F 0.50924(10) 0.71222(8) 0.25549(4) 0.0284(3) Uani 1 1 d . . .
O1 O 0.44340(10) 0.41835(8) 0.34427(5) 0.0195(3) Uani 1 1 d . . .
O2 O 0.62058(11) 0.40335(8) 0.31570(5) 0.0230(3) Uani 1 1 d . . .
H2O H 0.5957 0.4126 0.2834 0.034 Uiso 1 1 d R A .
O3 O 0.65592(12) 0.66030(8) 0.38809(5) 0.0241(3) Uani 1 1 d . . .
O4 O 0.59313(11) 0.57490(8) 0.29247(5) 0.0194(3) Uani 1 1 d . . .
H4O H 0.5548 0.6185 0.2813 0.029 Uiso 1 1 d R . .
O5 O 0.09843(10) 0.56708(8) 0.35369(5) 0.0195(3) Uani 1 1 d . . .
O6 O -0.01465(10) 0.68583(9) 0.34072(5) 0.0216(3) Uani 1 1 d . . .
H6O H 0.0072 0.6946 0.3083 0.032 Uiso 1 1 d R . .
O7 O 0.25207(13) 0.81185(10) 0.43021(6) 0.0288(3) Uani 1 1 d . . .
O8 O 0.18233(11) 0.77088(7) 0.32460(5) 0.0187(3) Uani 1 1 d . . .
H8O H 0.1335 0.8107 0.3286 0.028 Uiso 1 1 d R . .
O9 O 0.53623(16) 0.37349(12) 0.22142(7) 0.0436(4) Uani 1 1 d . . .
H9O H 0.5179 0.3189 0.2293 0.065 Uiso 1 1 d R A .
C25 C 0.4376(4) 0.4286(3) 0.21226(17) 0.0320(12) Uani 0.561(8) 1 d P A 1
H25A H 0.4553 0.4904 0.2188 0.038 Uiso 0.561(8) 1 calc PR A 1
H25B H 0.3785 0.4112 0.2364 0.038 Uiso 0.561(8) 1 calc PR A 1
C26 C 0.4009(4) 0.4170(3) 0.15687(17) 0.0425(14) Uani 0.561(8) 1 d P A 1
H26A H 0.4581 0.4376 0.1332 0.064 Uiso 0.561(8) 1 calc PR A 1
H26B H 0.3341 0.4506 0.1510 0.064 Uiso 0.561(8) 1 calc PR A 1
H26C H 0.3866 0.3553 0.1502 0.064 Uiso 0.561(8) 1 calc PR A 1
C25A C 0.4628(5) 0.3975(4) 0.1807(2) 0.0362(17) Uani 0.439(8) 1 d P A 2
H25C H 0.4209 0.3463 0.1685 0.043 Uiso 0.439(8) 1 calc PR A 2
H25D H 0.5030 0.4225 0.1508 0.043 Uiso 0.439(8) 1 calc PR A 2
C26A C 0.3880(6) 0.4639(6) 0.2043(3) 0.054(2) Uani 0.439(8) 1 d P A 2
H26D H 0.3412 0.4359 0.2304 0.080 Uiso 0.439(8) 1 calc PR A 2
H26E H 0.3426 0.4897 0.1770 0.080 Uiso 0.439(8) 1 calc PR A 2
H26F H 0.4314 0.5095 0.2211 0.080 Uiso 0.439(8) 1 calc PR A 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.371(2) . ?
C1 C2 1.387(2) . ?
C1 C6 1.394(2) . ?
C2 C3 1.389(2) . ?
C2 H2 0.9500 . ?
C3 O5 1.362(2) . ?
C3 C4 1.396(2) . ?
C4 C5 1.389(2) . ?
C4 C24 1.501(2) . ?
C5 C6 1.388(2) . ?
C5 H5 0.9500 . ?
C6 C15 1.511(2) . ?
C7 O2 1.363(2) . ?
C7 O1 1.482(2) . ?
C7 C8 1.509(3) . ?
C7 C15 1.571(2) . ?
C8 C9 1.391(3) . ?
C8 C13 1.392(3) . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.476(2) . ?
C14 O3 1.214(2) . ?
C14 C15 1.532(2) . ?
C15 O4 1.400(2) . ?
C16 O6 1.363(2) . ?
C16 O5 1.466(2) . ?
C16 C17 1.511(2) . ?
C16 C24 1.572(2) . ?
C17 C22 1.387(3) . ?
C17 C18 1.391(3) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.393(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.398(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.471(3) . ?
C23 O7 1.212(2) . ?
C23 C24 1.545(2) . ?
C24 O8 1.407(2) . ?
Cs1 O8 3.0575(13) . ?
Cs1 O6 3.0875(12) 6_656 ?
Cs1 F1 3.1181(13) . ?
Cs1 O4 3.1544(13) 6_556 ?
Cs1 O3 3.1711(14) 6_556 ?
Cs1 O2 3.1823(12) 3_655 ?
Cs1 F1 3.2695(13) 6_556 ?
F1 H4O 1.6812 . ?
F1 Cs1 3.2695(13) 6_656 ?
O2 Cs1 3.1823(12) 3_645 ?
O2 H2O 0.8935 . ?
O4 H4O 0.8680 . ?
O6 H6O 0.8848 . ?
O8 H8O 0.8625 . ?
O9 C25A 1.427(6) . ?
O9 C25 1.495(6) . ?
O9 H9O 0.8925 . ?
C25 C26 1.501(6) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C25A C26A 1.501(11) . ?
C25A H25C 0.9900 . ?
C25A H25D 0.9900 . ?
C26A H26D 0.9800 . ?
C26A H26E 0.9800 . ?
C26A H26F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 122.70(15) . . ?
O1 C1 C6 113.06(14) . . ?
C2 C1 C6 124.23(16) . . ?
C1 C2 C3 113.79(16) . . ?
C1 C2 H2 123.1 . . ?
C3 C2 H2 123.1 . . ?
O5 C3 C2 122.49(15) . . ?
O5 C3 C4 113.91(15) . . ?
C2 C3 C4 123.59(15) . . ?
C5 C4 C3 120.84(15) . . ?
C5 C4 C24 130.52(16) . . ?
C3 C4 C24 108.64(14) . . ?
C6 C5 C4 116.94(15) . . ?
C6 C5 H5 121.5 . . ?
C4 C5 H5 121.5 . . ?
C5 C6 C1 120.37(15) . . ?
C5 C6 C15 130.63(15) . . ?
C1 C6 C15 108.99(14) . . ?
O2 C7 O1 108.15(14) . . ?
O2 C7 C8 112.24(14) . . ?
O1 C7 C8 109.82(14) . . ?
O2 C7 C15 116.82(15) . . ?
O1 C7 C15 105.56(13) . . ?
C8 C7 C15 103.92(14) . . ?
C9 C8 C13 120.46(18) . . ?
C9 C8 C7 127.67(17) . . ?
C13 C8 C7 111.87(15) . . ?
C10 C9 C8 117.8(2) . . ?
C10 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
C9 C10 C11 121.81(19) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C10 C11 C12 120.8(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 117.5(2) . . ?
C11 C12 H12 121.3 . . ?
C13 C12 H12 121.3 . . ?
C12 C13 C8 121.70(17) . . ?
C12 C13 C14 128.84(17) . . ?
C8 C13 C14 109.46(16) . . ?
O3 C14 C13 128.12(17) . . ?
O3 C14 C15 124.32(16) . . ?
C13 C14 C15 107.54(14) . . ?
O3 C14 Cs1 47.82(9) . 6_656 ?
C13 C14 Cs1 146.11(11) . 6_656 ?
C15 C14 Cs1 85.89(9) . 6_656 ?
O4 C15 C6 114.87(14) . . ?
O4 C15 C14 113.30(14) . . ?
C6 C15 C14 110.28(14) . . ?
O4 C15 C7 111.82(14) . . ?
C6 C15 C7 101.35(13) . . ?
C14 C15 C7 104.07(14) . . ?
O6 C16 O5 109.90(14) . . ?
O6 C16 C17 111.64(14) . . ?
O5 C16 C17 108.12(14) . . ?
O6 C16 C24 115.70(14) . . ?
O5 C16 C24 106.51(13) . . ?
C17 C16 C24 104.54(14) . . ?
C22 C17 C18 121.26(18) . . ?
C22 C17 C16 111.55(16) . . ?
C18 C17 C16 127.20(18) . . ?
C19 C18 C17 117.6(2) . . ?
C19 C18 H18 121.2 . . ?
C17 C18 H18 121.2 . . ?
C18 C19 C20 121.1(2) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C21 C20 C19 121.5(2) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C22 117.3(2) . . ?
C20 C21 H21 121.3 . . ?
C22 C21 H21 121.3 . . ?
C17 C22 C21 121.16(19) . . ?
C17 C22 C23 110.50(16) . . ?
C21 C22 C23 128.31(19) . . ?
O7 C23 C22 128.10(17) . . ?
O7 C23 C24 124.36(17) . . ?
C22 C23 C24 107.54(15) . . ?
O8 C24 C4 110.82(14) . . ?
O8 C24 C23 113.39(14) . . ?
C4 C24 C23 110.96(14) . . ?
O8 C24 C16 115.13(14) . . ?
C4 C24 C16 101.73(13) . . ?
C23 C24 C16 104.08(14) . . ?
O8 Cs1 O6 140.69(4) . 6_656 ?
O8 Cs1 F1 92.86(3) . . ?
O6 Cs1 F1 47.86(3) 6_656 . ?
O8 Cs1 O4 89.99(3) . 6_556 ?
O6 Cs1 O4 114.53(3) 6_656 6_556 ?
F1 Cs1 O4 128.82(3) . 6_556 ?
O8 Cs1 O3 133.48(4) . 6_556 ?
O6 Cs1 O3 85.19(4) 6_656 6_556 ?
F1 Cs1 O3 131.81(3) . 6_556 ?
O4 Cs1 O3 54.30(3) 6_556 6_556 ?
O8 Cs1 O2 100.24(3) . 3_655 ?
O6 Cs1 O2 71.09(3) 6_656 3_655 ?
F1 Cs1 O2 74.38(3) . 3_655 ?
O4 Cs1 O2 154.47(3) 6_556 3_655 ?
O3 Cs1 O2 103.60(3) 6_556 3_655 ?
O8 Cs1 F1 58.31(3) . 6_556 ?
O6 Cs1 F1 158.64(3) 6_656 6_556 ?
F1 Cs1 F1 147.805(10) . 6_556 ?
O4 Cs1 F1 46.41(3) 6_556 6_556 ?
O3 Cs1 F1 75.17(3) 6_556 6_556 ?
O2 Cs1 F1 121.30(3) 3_655 6_556 ?
O8 Cs1 O9 71.61(4) . 3_655 ?
O6 Cs1 O9 76.47(4) 6_656 3_655 ?
F1 Cs1 O9 44.20(4) . 3_655 ?
O4 Cs1 O9 158.27(4) 6_556 3_655 ?
O3 Cs1 O9 147.43(4) 6_556 3_655 ?
O2 Cs1 O9 45.06(4) 3_655 3_655 ?
F1 Cs1 O9 124.83(4) 6_556 3_655 ?
O8 Cs1 C14 125.83(4) . 6_556 ?
O6 Cs1 C14 89.09(4) 6_656 6_556 ?
F1 Cs1 C14 130.11(3) . 6_556 ?
O4 Cs1 C14 39.33(3) 6_556 6_556 ?
O3 Cs1 C14 16.48(3) 6_556 6_556 ?
O2 Cs1 C14 119.92(4) 3_655 6_556 ?
F1 Cs1 C14 69.71(3) 6_556 6_556 ?
O9 Cs1 C14 161.86(4) 3_655 6_556 ?
H4O F1 Cs1 119.3 . . ?
H4O F1 Cs1 68.7 . 6_656 ?
Cs1 F1 Cs1 171.16(4) . 6_656 ?
C1 O1 C7 108.04(12) . . ?
C7 O2 Cs1 149.06(11) . 3_645 ?
C7 O2 H2O 108.2 . . ?
Cs1 O2 H2O 92.6 3_645 . ?
C14 O3 Cs1 115.71(11) . 6_656 ?
C15 O4 Cs1 120.34(10) . 6_656 ?
C15 O4 H4O 107.9 . . ?
Cs1 O4 H4O 77.6 6_656 . ?
C3 O5 C16 107.47(13) . . ?
C16 O6 Cs1 169.27(11) . 6_556 ?
C16 O6 H6O 109.3 . . ?
Cs1 O6 H6O 77.6 6_556 . ?
C24 O8 Cs1 122.36(9) . . ?
C24 O8 H8O 111.1 . . ?
Cs1 O8 H8O 121.0 . . ?
C25A O9 H2O 142.5 . . ?
C25 O9 H2O 105.6 . . ?
C25A O9 Cs1 152.7(3) . 3_645 ?
C25 O9 Cs1 161.32(19) . 3_645 ?
H2O O9 Cs1 64.8 . 3_645 ?
C25A O9 H9O 104.5 . . ?
C25 O9 H9O 111.4 . . ?
H2O O9 H9O 102.1 . . ?
Cs1 O9 H9O 58.5 3_645 . ?
O9 C25 C26 108.9(4) . . ?
O9 C25 H25A 109.9 . . ?
C26 C25 H25A 109.9 . . ?
O9 C25 H25B 109.9 . . ?
C26 C25 H25B 109.9 . . ?
H25A C25 H25B 108.3 . . ?
O9 C25A C26A 105.4(5) . . ?
O9 C25A H25C 110.7 . . ?
C26A C25A H25C 110.7 . . ?
O9 C25A H25D 110.7 . . ?
C26A C25A H25D 110.7 . . ?
H25C C25A H25D 108.8 . . ?
C25A C26A H26D 109.5 . . ?
C25A C26A H26E 109.5 . . ?
H26D C26A H26E 109.5 . . ?
C25A C26A H26F 109.5 . . ?
H26D C26A H26F 109.5 . . ?
H26E C26A H26F 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H9O F1 0.89 1.72 2.610(2) 176.6 3_645
O8 H8O O1 0.86 1.95 2.7884(17) 164.7 8_665
O6 H6O F1 0.88 1.66 2.5174(18) 163.3 6_556
O4 H4O F1 0.87 1.68 2.5334(17) 166.5 .
O2 H2O O9 0.89 1.85 2.670(2) 151.5 .

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.02
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.945
_refine_diff_density_rms         0.075
####################################################################### 
# 
# 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_maayan36
_audit_block_doi                 10.5517/cc140b7q
_database_code_depnum_ccdc_archive 'CCDC 1043002'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5DT04171F 2016
_audit_update_record             
;
2016-01-14 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Rubidium Fluoride complex of Vasarene [4]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H14 O8 F Rb, C2 O'
_chemical_formula_sum            'C26 H14 F O9 Rb'
_chemical_formula_weight         574.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Rb Rb -0.9393 2.9676 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.194(1)
_cell_length_b                   15.536(2)
_cell_length_c                   25.299(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4792.7(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(1)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      24.14

_exptl_crystal_description       Plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2304
_exptl_absorpt_coefficient_mu    2.129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5170
_exptl_absorpt_correction_T_max  0.7606
_exptl_absorpt_process_details   'Bruker SADABS V2.05'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            49580
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         27.00
_reflns_number_total             5225
_reflns_number_gt                3727
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0978P)²+4.5812P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5225
_refine_ls_number_parameters     369
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1775
_refine_ls_wR_factor_gt          0.1650
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.3800(3) 0.4943(2) 0.34427(15) 0.0277(8) Uani 1 1 d . . .
C2 C 0.2669(3) 0.4893(2) 0.34582(16) 0.0311(8) Uani 1 1 d . . .
H2 H 0.2288 0.4376 0.3433 0.037 Uiso 1 1 calc R . .
C3 C 0.2156(3) 0.5681(2) 0.35145(14) 0.0254(7) Uani 1 1 d . . .
C4 C 0.2719(3) 0.6461(2) 0.35640(14) 0.0255(7) Uani 1 1 d . . .
C5 C 0.3854(3) 0.6482(2) 0.35345(13) 0.0244(7) Uani 1 1 d . . .
H5 H 0.4238 0.6998 0.3560 0.029 Uiso 1 1 calc R . .
C6 C 0.4397(3) 0.5704(2) 0.34652(14) 0.0245(7) Uani 1 1 d . . .
C7 C 0.5602(3) 0.4511(2) 0.34635(16) 0.0301(8) Uani 1 1 d . . .
C8 C 0.5942(3) 0.4391(2) 0.40312(16) 0.0316(8) Uani 1 1 d . . .
C9 C 0.5901(4) 0.3644(3) 0.43329(19) 0.0456(11) Uani 1 1 d . . .
H9 H 0.5663 0.3128 0.4186 0.055 Uiso 1 1 calc R . .
C10 C 0.6221(4) 0.3686(3) 0.4854(2) 0.0541(13) Uani 1 1 d . . .
H10 H 0.6193 0.3192 0.5062 0.065 Uiso 1 1 calc R . .
C11 C 0.6588(4) 0.4457(3) 0.50764(19) 0.0543(12) Uani 1 1 d . . .
H11 H 0.6780 0.4476 0.5432 0.065 Uiso 1 1 calc R . .
C12 C 0.6668(4) 0.5192(3) 0.47708(17) 0.0426(10) Uani 1 1 d . . .
H12 H 0.6946 0.5701 0.4912 0.051 Uiso 1 1 calc R . .
C13 C 0.6326(3) 0.5152(2) 0.42498(15) 0.0308(8) Uani 1 1 d . . .
C14 C 0.6300(3) 0.5835(2) 0.38450(15) 0.0281(8) Uani 1 1 d . . .
C15 C 0.5598(3) 0.5510(2) 0.33876(14) 0.0268(7) Uani 1 1 d . . .
C16 C 0.0806(3) 0.6647(2) 0.37079(15) 0.0281(8) Uani 1 1 d . . .
C17 C 0.0622(3) 0.6639(3) 0.42995(16) 0.0349(9) Uani 1 1 d . . .
C18 C -0.0150(4) 0.6154(3) 0.4578(2) 0.0559(13) Uani 1 1 d . . .
H18 H -0.0632 0.5784 0.4406 0.067 Uiso 1 1 calc R . .
C19 C -0.0163(5) 0.6250(4) 0.5123(2) 0.0736(19) Uani 1 1 d . . .
H19 H -0.0656 0.5928 0.5321 0.088 Uiso 1 1 calc R . .
C20 C 0.0535(6) 0.6810(4) 0.5378(2) 0.0692(17) Uani 1 1 d . . .
H20 H 0.0486 0.6868 0.5743 0.083 Uiso 1 1 calc R . .
C21 C 0.1308(5) 0.7287(3) 0.51046(19) 0.0546(13) Uani 1 1 d . . .
H21 H 0.1786 0.7657 0.5279 0.065 Uiso 1 1 calc R . .
C22 C 0.1337(4) 0.7189(2) 0.45552(16) 0.0359(9) Uani 1 1 d . . .
C23 C 0.2059(3) 0.7622(2) 0.41771(16) 0.0299(8) Uani 1 1 d . . .
C24 C 0.1897(3) 0.7173(2) 0.36385(14) 0.0250(7) Uani 1 1 d . . .
F1 F 0.5016(3) 0.7039(2) 0.25289(11) 0.0654(9) Uani 1 1 d . . .
O1 O 0.4452(2) 0.42252(15) 0.33958(11) 0.0330(6) Uani 1 1 d . . .
O2 O 0.6245(2) 0.40541(19) 0.31144(12) 0.0414(7) Uani 1 1 d D . .
H2O H 0.610(5) 0.425(4) 0.2815(11) 0.065(19) Uiso 1 1 d D . .
O3 O 0.6761(3) 0.65253(18) 0.38528(12) 0.0436(7) Uani 1 1 d . . .
O4 O 0.6023(2) 0.57448(19) 0.28912(11) 0.0350(6) Uani 1 1 d D . .
H4O H 0.557(6) 0.610(5) 0.277(3) 0.14(4) Uiso 1 1 d D . .
O5 O 0.1044(2) 0.57678(16) 0.35333(11) 0.0329(6) Uani 1 1 d . . .
O6 O -0.0083(2) 0.69610(19) 0.34461(12) 0.0373(7) Uani 1 1 d D . .
H6O H 0.006(4) 0.696(4) 0.3121(6) 0.056(16) Uiso 1 1 d D . .
O7 O 0.2671(3) 0.8217(2) 0.42523(13) 0.0484(8) Uani 1 1 d . . .
O8 O 0.1921(2) 0.77364(17) 0.32024(11) 0.0333(6) Uani 1 1 d D . .
H8O H 0.138(3) 0.806(3) 0.323(2) 0.067(17) Uiso 1 1 d D . .
Rb1 Rb 0.27525(3) 0.72568(3) 0.212775(18) 0.04630(18) Uani 1 1 d . . .
O9A O 0.5311(9) 0.3679(7) 0.2187(4) 0.104(3) Uani 0.50 1 d PD . .
O9B O 0.4176(7) 0.3254(6) 0.1932(4) 0.097(3) Uani 0.50 1 d P . .
C25 C 0.4600(7) 0.4069(6) 0.1858(4) 0.111(3) Uani 1 1 d D . .
C26A C 0.3893(14) 0.4756(13) 0.1976(8) 0.089(5) Uani 0.50 1 d P . .
C26B C 0.3803(14) 0.4603(13) 0.1618(9) 0.097(6) Uani 0.50 1 d P . .


_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 O1 1.374(4) . ?
C1 C2 1.382(5) . ?
C1 C6 1.389(5) . ?
C2 C3 1.382(5) . ?
C2 H2 0.9300 . ?
C3 O5 1.364(4) . ?
C3 C4 1.398(5) . ?
C4 C5 1.387(5) . ?
C4 C24 1.505(5) . ?
C5 C6 1.390(5) . ?
C5 H5 0.9300 . ?
C6 C15 1.508(5) . ?
C7 O2 1.377(5) . ?
C7 O1 1.482(4) . ?
C7 C8 1.506(5) . ?
C7 C15 1.564(5) . ?
C8 C13 1.386(5) . ?
C8 C9 1.390(6) . ?
C9 C10 1.376(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.398(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.475(5) . ?
C14 O3 1.212(4) . ?
C14 C15 1.525(5) . ?
C15 O4 1.407(4) . ?
C16 O6 1.361(4) . ?
C16 O5 1.464(4) . ?
C16 C17 1.513(5) . ?
C16 C24 1.572(5) . ?
C17 C22 1.381(6) . ?
C17 C18 1.397(6) . ?
C18 C19 1.387(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.376(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.385(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.399(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.464(6) . ?
C23 O7 1.203(5) . ?
C23 C24 1.543(5) . ?
C24 O8 1.408(4) . ?
F1 H4O 1.72(3) . ?
F1 Rb1 2.960(4) . ?
F1 Rb1 3.465(4) 6_656 ?
O2 Rb1 3.109(3) 3_645 ?
O2 H2O 0.838(10) . ?
O3 Rb1 2.984(3) 6_656 ?
O4 Rb1 3.157(3) 6_656 ?
O4 H4O 0.837(10) . ?
O6 Rb1 3.047(3) 6_556 ?
O6 H6O 0.840(10) . ?
O8 Rb1 2.996(3) . ?
O8 H8O 0.839(10) . ?
Rb1 O9B 2.859(8) 8_665 ?
Rb1 O3 2.984(3) 6_556 ?
Rb1 O6 3.047(3) 6_656 ?
Rb1 O2 3.109(3) 3_655 ?
Rb1 O4 3.157(3) 6_556 ?
Rb1 F1 3.465(4) 6_556 ?
O9A C25 1.346(8) . ?
O9B C25 1.381(11) . ?
O9B Rb1 2.859(8) 8_655 ?
C25 C26A 1.40(2) . ?
C25 C26B 1.42(2) . ?

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 122.2(3) . . ?
O1 C1 C6 113.0(3) . . ?
C2 C1 C6 124.7(3) . . ?
C1 C2 C3 113.9(3) . . ?
C1 C2 H2 123.1 . . ?
C3 C2 H2 123.1 . . ?
O5 C3 C2 122.8(3) . . ?
O5 C3 C4 113.5(3) . . ?
C2 C3 C4 123.7(3) . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 C24 130.8(3) . . ?
C3 C4 C24 108.8(3) . . ?
C4 C5 C6 117.5(3) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C1 C6 C5 119.7(3) . . ?
C1 C6 C15 109.5(3) . . ?
C5 C6 C15 130.8(3) . . ?
O2 C7 O1 108.1(3) . . ?
O2 C7 C8 113.0(3) . . ?
O1 C7 C8 109.5(3) . . ?
O2 C7 C15 115.7(3) . . ?
O1 C7 C15 106.3(3) . . ?
C8 C7 C15 103.9(3) . . ?
C13 C8 C9 120.3(4) . . ?
C13 C8 C7 111.6(3) . . ?
C9 C8 C7 128.1(4) . . ?
C10 C9 C8 118.4(4) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C10 C11 121.1(4) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 120.4(4) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 118.3(4) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C12 C13 C8 121.3(4) . . ?
C12 C13 C14 129.5(4) . . ?
C8 C13 C14 109.2(3) . . ?
O3 C14 C13 128.0(4) . . ?
O3 C14 C15 124.5(3) . . ?
C13 C14 C15 107.5(3) . . ?
O4 C15 C6 115.0(3) . . ?
O4 C15 C14 112.6(3) . . ?
C6 C15 C14 112.3(3) . . ?
O4 C15 C7 111.5(3) . . ?
C6 C15 C7 100.7(3) . . ?
C14 C15 C7 103.5(3) . . ?
O6 C16 O5 110.2(3) . . ?
O6 C16 C17 111.4(3) . . ?
O5 C16 C17 108.7(3) . . ?
O6 C16 C24 115.7(3) . . ?
O5 C16 C24 106.5(3) . . ?
C17 C16 C24 103.9(3) . . ?
C22 C17 C18 121.5(4) . . ?
C22 C17 C16 111.4(3) . . ?
C18 C17 C16 127.1(4) . . ?
C19 C18 C17 116.8(5) . . ?
C19 C18 H18 121.6 . . ?
C17 C18 H18 121.6 . . ?
C20 C19 C18 121.8(5) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C19 C20 C21 121.7(5) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C20 C21 C22 117.1(5) . . ?
C20 C21 H21 121.5 . . ?
C22 C21 H21 121.5 . . ?
C17 C22 C21 121.1(4) . . ?
C17 C22 C23 111.0(3) . . ?
C21 C22 C23 127.9(4) . . ?
O7 C23 C22 128.5(4) . . ?
O7 C23 C24 124.5(4) . . ?
C22 C23 C24 107.0(3) . . ?
O8 C24 C4 110.2(3) . . ?
O8 C24 C23 114.1(3) . . ?
C4 C24 C23 111.0(3) . . ?
O8 C24 C16 115.4(3) . . ?
C4 C24 C16 101.2(3) . . ?
C23 C24 C16 104.2(3) . . ?
H4O F1 Rb1 126(3) . . ?
H4O F1 Rb1 67(3) . 6_656 ?
Rb1 F1 Rb1 166.60(11) . 6_656 ?
C1 O1 C7 107.1(3) . . ?
C7 O2 Rb1 144.4(3) . 3_645 ?
C7 O2 H2O 106(4) . . ?
Rb1 O2 H2O 104(4) 3_645 . ?
C14 O3 Rb1 120.8(2) . 6_656 ?
C15 O4 Rb1 116.9(2) . 6_656 ?
C15 O4 H4O 106(6) . . ?
Rb1 O4 H4O 87(7) 6_656 . ?
C3 O5 C16 107.5(3) . . ?
C16 O6 Rb1 167.4(2) . 6_556 ?
C16 O6 H6O 108(4) . . ?
Rb1 O6 H6O 74(4) 6_556 . ?
C24 O8 Rb1 124.3(2) . . ?
C24 O8 H8O 107(4) . . ?
Rb1 O8 H8O 120(4) . . ?
O9B Rb1 F1 152.7(2) 8_665 . ?
O9B Rb1 O3 74.3(3) 8_665 6_556 ?
F1 Rb1 O3 128.24(9) . 6_556 ?
O9B Rb1 O8 75.2(2) 8_665 . ?
F1 Rb1 O8 91.89(8) . . ?
O3 Rb1 O8 135.40(8) 6_556 . ?
O9B Rb1 O6 135.38(19) 8_665 6_656 ?
F1 Rb1 O6 48.58(8) . 6_656 ?
O3 Rb1 O6 84.10(9) 6_556 6_656 ?
O8 Rb1 O6 139.74(8) . 6_656 ?
O9B Rb1 O2 78.6(2) 8_665 3_655 ?
F1 Rb1 O2 78.68(9) . 3_655 ?
O3 Rb1 O2 109.72(8) 6_556 3_655 ?
O8 Rb1 O2 95.08(8) . 3_655 ?
O6 Rb1 O2 72.60(8) 6_656 3_655 ?
O9B Rb1 O4 81.4(2) 8_665 6_556 ?
F1 Rb1 O4 122.88(8) . 6_556 ?
O3 Rb1 O4 55.49(7) 6_556 6_556 ?
O8 Rb1 O4 88.44(7) . 6_556 ?
O6 Rb1 O4 117.32(8) 6_656 6_556 ?
O2 Rb1 O4 158.11(8) 3_655 6_556 ?
O9B Rb1 F1 45.90(18) 8_665 6_556 ?
F1 Rb1 F1 143.21(4) . 6_556 ?
O3 Rb1 F1 77.36(8) 6_556 6_556 ?
O8 Rb1 F1 58.05(7) . 6_556 ?
O6 Rb1 F1 159.87(8) 6_656 6_556 ?
O2 Rb1 F1 121.06(8) 3_655 6_556 ?
O4 Rb1 F1 44.59(7) 6_556 6_556 ?
C25 O9A H2O 125.6(16) . . ?
C25 O9B Rb1 145.9(7) . 8_655 ?
O9A C25 O9B 75.1(7) . . ?
O9A C25 C26A 127.2(14) . . ?
O9B C25 C26B 109.8(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O8 H8O O1 0.839(10) 2.11(3) 2.897(4) 156(5) 8_665
O6 H6O F1 0.840(10) 1.651(17) 2.473(4) 165(5) 6_556
O4 H4O F1 0.837(10) 1.72(3) 2.528(4) 161(10) .
O2 H2O O9A 0.838(10) 2.06(5) 2.673(10) 130(5) .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.116
_refine_diff_density_min         -0.981
_refine_diff_density_rms         0.097
####################################################################### 
# 
# 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_maayan39a
_audit_block_doi                 10.5517/cc140b8r
_database_code_depnum_ccdc_archive 'CCDC 1043003'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5DT04171F 2016
_audit_update_record             
;
2016-01-14 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            
'Tetramethyl Ammonium Fluoride complex of Vasarene [4]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H27 O16, 2(C4 H12 N), 2(C2 H6 O), F,H2 O'
_chemical_formula_sum            'C60 H65 F N2 O19'
_chemical_formula_weight         1130.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.749(1)
_cell_length_b                   11.785(1)
_cell_length_c                   14.738(2)
_cell_angle_alpha                70.446(2)
_cell_angle_beta                 86.671(2)
_cell_angle_gamma                71.563(2)
_cell_volume                     1511.5(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(1)
_cell_measurement_reflns_used    4958
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.10

_exptl_crystal_description       shapeless
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             593
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9603
_exptl_absorpt_correction_T_max  0.9831
_exptl_absorpt_process_details   'Bruker SADABS V2.05'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16120
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         27.00
_reflns_number_total             6446
_reflns_number_gt                4633
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1502P)²+0.1535P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6446
_refine_ls_number_parameters     412
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0744
_refine_ls_wR_factor_ref         0.2343
_refine_ls_wR_factor_gt          0.2160
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001

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 0.6741(2) 0.37299(19) 0.29005(13) 0.0336(5) Uani 1 1 d . . .
C2 C 0.7757(2) 0.25304(19) 0.31526(13) 0.0318(4) Uani 1 1 d . . .
C3 C 0.8196(2) 0.18576(18) 0.41175(13) 0.0306(4) Uani 1 1 d . . .
H3 H 0.8880 0.1054 0.4298 0.037 Uiso 1 1 calc R . .
C4 C 0.7596(2) 0.24063(18) 0.48032(13) 0.0306(4) Uani 1 1 d . . .
C5 C 0.6552(2) 0.3624(2) 0.45354(14) 0.0353(5) Uani 1 1 d . . .
C6 C 0.6109(2) 0.4300(2) 0.35655(15) 0.0377(5) Uani 1 1 d . . .
H6 H 0.5417 0.5099 0.3377 0.045 Uiso 1 1 calc R . .
C7 C 0.7058(2) 0.3318(2) 0.14823(14) 0.0373(5) Uani 1 1 d . . .
C8 C 0.5931(2) 0.2731(2) 0.13932(15) 0.0405(5) Uani 1 1 d . . .
C9 C 0.4553(3) 0.3346(3) 0.09480(18) 0.0523(6) Uani 1 1 d . . .
H9 H 0.4236 0.4220 0.0635 0.063 Uiso 1 1 calc R . .
C10 C 0.3665(3) 0.2620(4) 0.0985(2) 0.0714(9) Uani 1 1 d . . .
H10 H 0.2741 0.3014 0.0687 0.086 Uiso 1 1 calc R . .
C11 C 0.4123(4) 0.1315(3) 0.1458(3) 0.0742(9) Uani 1 1 d . . .
H11 H 0.3499 0.0851 0.1484 0.089 Uiso 1 1 calc R . .
C12 C 0.5500(3) 0.0704(3) 0.1890(2) 0.0610(7) Uani 1 1 d . . .
H12 H 0.5824 -0.0172 0.2192 0.073 Uiso 1 1 calc R . .
C13 C 0.6385(3) 0.1428(2) 0.18606(16) 0.0435(5) Uani 1 1 d . . .
C14 C 0.7860(3) 0.1020(2) 0.23029(14) 0.0402(5) Uani 1 1 d . . .
C15 C 0.8221(2) 0.2206(2) 0.22539(14) 0.0360(5) Uani 1 1 d . . .
C16 C 0.8011(2) 0.17755(19) 0.58633(14) 0.0344(5) Uani 1 1 d . . .
C17 C 0.6700(3) 0.1615(2) 0.64807(15) 0.0392(5) Uani 1 1 d . . .
C18 C 0.6743(3) 0.2083(2) 0.72898(15) 0.0430(6) Uani 1 1 d . . .
C19 C 0.5864(4) 0.2054(3) 0.8069(2) 0.0645(8) Uani 1 1 d . . .
H19 H 0.5143 0.1672 0.8150 0.077 Uiso 1 1 calc R . .
C20 C 0.6076(4) 0.2594(4) 0.8711(2) 0.0780(10) Uani 1 1 d . . .
H20 H 0.5489 0.2585 0.9232 0.094 Uiso 1 1 calc R . .
C21 C 0.7151(4) 0.3154(3) 0.8600(2) 0.0786(10) Uani 1 1 d . . .
H21 H 0.7280 0.3511 0.9051 0.094 Uiso 1 1 calc R . .
C22 C 0.8038(4) 0.3194(3) 0.7831(2) 0.0645(8) Uani 1 1 d . . .
H22 H 0.8755 0.3579 0.7755 0.077 Uiso 1 1 calc R . .
C23 C 0.7823(3) 0.2640(2) 0.71742(16) 0.0431(6) Uani 1 1 d . . .
C24 C 0.8578(2) 0.2587(2) 0.62869(16) 0.0406(5) Uani 1 1 d . . .
C25 C 0.5940(5) 0.7969(6) 0.6135(4) 0.1175(18) Uani 1 1 d . . .
H25A H 0.5156 0.8097 0.5708 0.176 Uiso 1 1 calc R . .
H25B H 0.5839 0.8745 0.6250 0.176 Uiso 1 1 calc R . .
H25C H 0.5922 0.7319 0.6735 0.176 Uiso 1 1 calc R . .
C26 C 0.7399(6) 0.8692(5) 0.4865(4) 0.1162(16) Uani 1 1 d . . .
H26A H 0.8385 0.8591 0.4694 0.174 Uiso 1 1 calc R . .
H26B H 0.7023 0.9441 0.5044 0.174 Uiso 1 1 calc R . .
H26C H 0.6828 0.8772 0.4325 0.174 Uiso 1 1 calc R . .
C27 C 0.7355(5) 0.6554(5) 0.5313(4) 0.1076(14) Uani 1 1 d . . .
H27A H 0.6579 0.6862 0.4833 0.161 Uiso 1 1 calc R . .
H27B H 0.7234 0.5845 0.5832 0.161 Uiso 1 1 calc R . .
H27C H 0.8263 0.6292 0.5031 0.161 Uiso 1 1 calc R . .
C28 C 0.8584(7) 0.7257(8) 0.6334(4) 0.169(3) Uani 1 1 d . . .
H28A H 0.8370 0.6859 0.6985 0.253 Uiso 1 1 calc R . .
H28B H 0.8791 0.8018 0.6287 0.253 Uiso 1 1 calc R . .
H28C H 0.9410 0.6686 0.6155 0.253 Uiso 1 1 calc R . .
C29 C 0.7983(11) 0.6750(10) 0.1593(6) 0.101(3) Uani 0.50 1 d P . .
H29A H 0.7554 0.6109 0.1599 0.121 Uiso 0.50 1 calc PR . .
H29B H 0.7322 0.7558 0.1202 0.121 Uiso 0.50 1 calc PR . .
C30 C 0.7953(11) 0.6777(14) 0.2526(8) 0.136(4) Uani 0.50 1 d P . .
H30A H 0.8302 0.5925 0.2970 0.204 Uiso 0.50 1 calc PR . .
H30B H 0.6977 0.7174 0.2660 0.204 Uiso 0.50 1 calc PR . .
H30C H 0.8558 0.7249 0.2594 0.204 Uiso 0.50 1 calc PR . .
C31 C 0.948(2) 0.9492(12) -0.0398(9) 0.164(7) Uani 0.50 1 d P . .
C32 C 0.932(3) 0.9906(16) 0.0353(9) 0.276(17) Uani 0.50 1 d P . .
F1 F 0.9773(5) 0.4254(5) 0.1068(4) 0.0887(12) Uani 0.50 1 d P . .
N1 N 0.7339(3) 0.7573(3) 0.56872(19) 0.0666(7) Uani 1 1 d . . .
O1 O 0.64174(18) 0.42944(14) 0.19258(10) 0.0420(4) Uani 1 1 d . . .
O2 O 0.75456(19) 0.38538(17) 0.06100(10) 0.0480(4) Uani 1 1 d . . .
H1O2 H 0.8215 0.4223 0.0720 0.072 Uiso 1 1 d R . .
O3 O 0.8654(2) -0.00579(16) 0.26612(13) 0.0592(5) Uani 1 1 d . . .
O4 O 0.96864(18) 0.20684(19) 0.20742(12) 0.0551(5) Uani 1 1 d . . .
H1O4 H 0.9794 0.2816 0.1792 0.083 Uiso 1 1 d R . .
O5 O 0.60332(18) 0.40587(15) 0.52483(11) 0.0482(5) Uani 1 1 d . . .
H1O5 H 0.5000 0.5000 0.5000 0.15(3) Uiso 1 2 d S . .
O6 O 0.9033(2) 0.05585(15) 0.60289(11) 0.0543(5) Uani 1 1 d . . .
H1O6 H 0.9539 0.0293 0.6561 0.081 Uiso 1 1 d R . .
O7 O 0.5838(2) 0.1136(2) 0.63363(14) 0.0641(5) Uani 1 1 d . . .
O8 O 0.9500(2) 0.3059(2) 0.59504(15) 0.0632(5) Uani 1 1 d . . .
O9 O 0.9146(6) 0.6552(6) 0.1122(4) 0.0921(16) Uani 0.50 1 d P . .
H9O H 0.9624 0.5771 0.1338 0.138 Uiso 0.50 1 d PR . .
O10 O 0.9364(6) 0.8484(6) -0.0516(4) 0.0961(17) Uani 0.50 1 d P . .
H10O H 0.9241 0.7977 0.0021 0.144 Uiso 0.50 1 d PR . .
O1W O 0.9249(12) 0.5240(10) 0.0561(6) 0.157(3) Uani 0.50 1 d P . .


_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 O1 1.373(2) . ?
C1 C6 1.378(3) . ?
C1 C2 1.386(3) . ?
C2 C3 1.391(3) . ?
C2 C15 1.505(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.413(3) . ?
C4 C16 1.504(3) . ?
C5 O5 1.325(2) . ?
C5 C6 1.398(3) . ?
C6 H6 0.9300 . ?
C7 O2 1.361(3) . ?
C7 O1 1.464(3) . ?
C7 C8 1.504(3) . ?
C7 C15 1.583(3) . ?
C8 C13 1.388(3) . ?
C8 C9 1.389(3) . ?
C9 C10 1.384(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.392(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.478(3) . ?
C14 O3 1.212(3) . ?
C14 C15 1.525(3) . ?
C15 O4 1.406(3) . ?
C16 O6 1.414(2) . ?
C16 C24 1.544(3) . ?
C16 C17 1.549(3) . ?
C17 O7 1.213(3) . ?
C17 C18 1.480(3) . ?
C18 C23 1.382(4) . ?
C18 C19 1.390(3) . ?
C19 C20 1.362(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.380(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.382(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.393(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.473(3) . ?
C24 O8 1.202(3) . ?
C25 N1 1.487(5) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 N1 1.477(5) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 N1 1.475(5) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 N1 1.460(5) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 O9 1.293(10) . ?
C29 C30 1.383(13) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 O10 1.296(14) . ?
C31 C32 1.334(18) . ?
C31 C32 1.56(4) 2_775 ?
C32 C31 1.56(4) 2_775 ?
C32 C32 1.66(6) 2_775 ?
O2 H1O2 0.9378 . ?
O4 H1O4 0.8771 . ?
O5 H1O5 1.2014 . ?
O6 H1O6 0.8596 . ?
O9 H9O 0.8461 . ?
O10 H10O 0.8451 . ?

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 C6 123.12(18) . . ?
O1 C1 C2 113.67(17) . . ?
C6 C1 C2 123.21(18) . . ?
C1 C2 C3 119.60(17) . . ?
C1 C2 C15 109.21(17) . . ?
C3 C2 C15 131.17(17) . . ?
C4 C3 C2 118.74(17) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 120.97(17) . . ?
C3 C4 C16 123.22(16) . . ?
C5 C4 C16 115.81(16) . . ?
O5 C5 C6 123.49(18) . . ?
O5 C5 C4 116.22(17) . . ?
C6 C5 C4 120.29(17) . . ?
C1 C6 C5 117.19(18) . . ?
C1 C6 H6 121.4 . . ?
C5 C6 H6 121.4 . . ?
O2 C7 O1 109.14(17) . . ?
O2 C7 C8 111.96(17) . . ?
O1 C7 C8 108.49(17) . . ?
O2 C7 C15 116.77(18) . . ?
O1 C7 C15 106.22(15) . . ?
C8 C7 C15 103.81(17) . . ?
C13 C8 C9 120.3(2) . . ?
C13 C8 C7 112.04(19) . . ?
C9 C8 C7 127.6(2) . . ?
C10 C9 C8 117.9(3) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C9 C10 C11 121.5(3) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 118.2(3) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C12 C13 C8 121.6(2) . . ?
C12 C13 C14 128.8(2) . . ?
C8 C13 C14 109.5(2) . . ?
O3 C14 C13 127.3(2) . . ?
O3 C14 C15 124.8(2) . . ?
C13 C14 C15 107.90(18) . . ?
O4 C15 C2 113.75(17) . . ?
O4 C15 C14 111.26(18) . . ?
C2 C15 C14 109.38(17) . . ?
O4 C15 C7 117.04(18) . . ?
C2 C15 C7 100.63(15) . . ?
C14 C15 C7 103.84(17) . . ?
O6 C16 C4 109.73(15) . . ?
O6 C16 C24 111.35(17) . . ?
C4 C16 C24 112.52(18) . . ?
O6 C16 C17 108.03(18) . . ?
C4 C16 C17 112.78(17) . . ?
C24 C16 C17 102.18(16) . . ?
O7 C17 C18 126.9(2) . . ?
O7 C17 C16 125.03(19) . . ?
C18 C17 C16 107.97(19) . . ?
C23 C18 C19 120.5(2) . . ?
C23 C18 C17 110.0(2) . . ?
C19 C18 C17 129.4(3) . . ?
C20 C19 C18 118.9(3) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C19 C20 C21 120.9(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C20 C21 C22 121.2(3) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C21 C22 C23 117.9(3) . . ?
C21 C22 H22 121.0 . . ?
C23 C22 H22 121.0 . . ?
C18 C23 C22 120.5(2) . . ?
C18 C23 C24 110.6(2) . . ?
C22 C23 C24 128.8(3) . . ?
O8 C24 C23 127.0(2) . . ?
O8 C24 C16 125.0(2) . . ?
C23 C24 C16 108.1(2) . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N1 C26 H26A 109.5 . . ?
N1 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N1 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N1 C27 H27A 109.5 . . ?
N1 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N1 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N1 C28 H28A 109.5 . . ?
N1 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N1 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O9 C29 C30 124.1(8) . . ?
O9 C29 H29A 106.3 . . ?
C30 C29 H29A 106.3 . . ?
O9 C29 H29B 106.3 . . ?
C30 C29 H29B 106.3 . . ?
H29A C29 H29B 106.4 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O10 C31 C32 133.4(17) . . ?
O10 C31 C32 139.0(16) . 2_775 ?
C32 C31 C32 69(2) . 2_775 ?
C31 C32 C31 111(2) . 2_775 ?
C31 C32 C32 61.8(10) . 2_775 ?
C31 C32 C32 49(2) 2_775 2_775 ?
C28 N1 C27 114.0(5) . . ?
C28 N1 C26 105.7(4) . . ?
C27 N1 C26 108.5(3) . . ?
C28 N1 C25 112.3(4) . . ?
C27 N1 C25 109.5(3) . . ?
C26 N1 C25 106.5(4) . . ?
C1 O1 C7 107.06(15) . . ?
C7 O2 H1O2 107.1 . . ?
C15 O4 H1O4 109.9 . . ?
C5 O5 H1O5 113.27 . . ?
C16 O6 H1O6 112.2 . . ?
C29 O9 H9O 108.6 . . ?
C31 O10 H10O 109.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O10 H10O O9 0.85 1.93 2.761(8) 168.0 .
O9 H9O F1 0.85 1.92 2.610(8) 138.0 .
O6 H1O6 O3 0.86 2.05 2.839(3) 152.0 2_756
O4 H1O4 F1 0.88 1.67 2.531(6) 167.8 .
O2 H1O2 F1 0.94 1.65 2.535(5) 156.6 .

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.956
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.072

# end Validation Reply Form

#                                                   END of  Ben-Giat_9.cif
#_______________________________________________________________________________
# 
#                                                   END of data_global
####################################################################### 
# 
# 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_Maayan29
_audit_block_doi                 10.5517/cc140b9s
_database_code_depnum_ccdc_archive 'CCDC 1043004'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5DT04171F 2016
_audit_update_record             
;
2016-01-14 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            
'Tetraethyl Ammonium Fluoride complex of Vasarene [4]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H14 O8, C8 H20 N, C2 H6 O, F '
_chemical_formula_sum            'C34 H40 F N O9'
_chemical_formula_weight         625.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)
_symmetry_space_group_name_Hall  'P 2yb'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5145(7)
_cell_length_b                   16.653(1)
_cell_length_c                   9.5978(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.788(1)
_cell_angle_gamma                90.00
_cell_volume                     1515.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(1)
_cell_measurement_reflns_used    5918
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      26.58

_exptl_crystal_description       Plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9599
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_process_details   'Bruker SADABS V2.05'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17714
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         28.04
_reflns_number_total             7122
_reflns_number_gt                6709
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0697P)²+0.2621P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_chemical_absolute_configuration unk
_refine_ls_number_reflns         7122
_refine_ls_number_parameters     416
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1294
_refine_ls_wR_factor_gt          0.1275
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.135
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.0899(2) 0.08275(12) 0.7482(2) 0.0156(4) Uani 1 1 d . . .
H1A H 0.0873 0.0302 0.7864 0.019 Uiso 1 1 calc R . .
C2 C -0.0104(2) 0.10841(12) 0.6450(2) 0.0155(4) Uani 1 1 d . . .
C3 C -0.1367(2) 0.06569(12) 0.5771(2) 0.0146(4) Uani 1 1 d . . .
C4 C -0.0913(2) -0.00100(13) 0.4779(2) 0.0159(4) Uani 1 1 d . . .
C5 C -0.1203(2) 0.02711(13) 0.3325(2) 0.0191(4) Uani 1 1 d . . .
C6 C -0.0913(3) -0.01172(16) 0.2099(3) 0.0283(5) Uani 1 1 d . . .
H6A H -0.0415 -0.0612 0.2124 0.034 Uiso 1 1 calc R . .
C7 C -0.1372(3) 0.02387(17) 0.0840(3) 0.0327(6) Uani 1 1 d . . .
H7 H -0.1170 -0.0007 -0.0014 0.039 Uiso 1 1 calc R . .
C8 C -0.2130(3) 0.09564(17) 0.0820(3) 0.0313(6) Uani 1 1 d . . .
H8 H -0.2468 0.1181 -0.0055 0.038 Uiso 1 1 calc R . .
C9 C -0.2401(3) 0.13497(15) 0.2033(2) 0.0251(5) Uani 1 1 d . . .
H9 H -0.2907 0.1842 0.2006 0.030 Uiso 1 1 calc R . .
C10 C -0.1906(2) 0.09992(13) 0.3300(2) 0.0178(4) Uani 1 1 d . . .
C11 C -0.2060(2) 0.13172(12) 0.4747(2) 0.0160(4) Uani 1 1 d . . .
C12 C -0.0066(2) 0.18629(13) 0.5914(2) 0.0159(4) Uani 1 1 d . . .
C13 C 0.0968(2) 0.24181(13) 0.6342(2) 0.0178(4) Uani 1 1 d . . .
H13 H 0.0995 0.2944 0.5960 0.021 Uiso 1 1 calc R . .
C14 C 0.1956(2) 0.21431(13) 0.7371(2) 0.0161(4) Uani 1 1 d . . .
C15 C 0.3631(2) 0.21986(13) 0.9227(2) 0.0172(4) Uani 1 1 d . . .
C16 C 0.2860(2) 0.25076(14) 1.0436(2) 0.0175(4) Uani 1 1 d . . .
C17 C 0.2705(3) 0.32972(14) 1.0857(2) 0.0219(5) Uani 1 1 d . . .
H17 H 0.3183 0.3721 1.0433 0.026 Uiso 1 1 calc R . .
C18 C 0.1833(3) 0.34509(15) 1.1914(2) 0.0264(5) Uani 1 1 d . . .
H18 H 0.1707 0.3989 1.2209 0.032 Uiso 1 1 calc R . .
C19 C 0.1139(3) 0.28340(16) 1.2551(2) 0.0261(5) Uani 1 1 d . . .
H19 H 0.0536 0.2958 1.3262 0.031 Uiso 1 1 calc R . .
C20 C 0.1315(2) 0.20391(15) 1.2162(2) 0.0237(5) Uani 1 1 d . . .
H20 H 0.0860 0.1614 1.2608 0.028 Uiso 1 1 calc R . .
C21 C 0.2185(2) 0.18890(14) 1.1092(2) 0.0180(4) Uani 1 1 d . . .
C22 C 0.2503(2) 0.11097(13) 1.0456(2) 0.0171(4) Uani 1 1 d . . .
C23 C 0.3145(2) 0.12941(13) 0.9071(2) 0.0159(4) Uani 1 1 d . . .
C24 C 0.1946(2) 0.13709(13) 0.7935(2) 0.0164(4) Uani 1 1 d . . .
C25 C 0.5950(3) 0.40930(17) 0.6968(3) 0.0306(5) Uani 1 1 d . . .
H25A H 0.5980 0.3512 0.7187 0.037 Uiso 1 1 calc R . .
H25B H 0.6876 0.4323 0.7304 0.037 Uiso 1 1 calc R . .
C26 C 0.4825(4) 0.4480(2) 0.7772(4) 0.0495(8) Uani 1 1 d . . .
H26A H 0.4703 0.5041 0.7481 0.074 Uiso 1 1 calc R . .
H26B H 0.5113 0.4457 0.8776 0.074 Uiso 1 1 calc R . .
H26C H 0.3933 0.4191 0.7579 0.074 Uiso 1 1 calc R . .
C27 C 0.4380(3) 0.38196(16) 0.4784(3) 0.0338(6) Uani 1 1 d . . .
H27A H 0.4227 0.3968 0.3784 0.041 Uiso 1 1 calc R . .
H27B H 0.3598 0.4054 0.5268 0.041 Uiso 1 1 calc R . .
C28 C 0.4306(3) 0.29134(16) 0.4903(3) 0.0307(6) Uani 1 1 d . . .
H28A H 0.4965 0.2669 0.4295 0.046 Uiso 1 1 calc R . .
H28B H 0.3346 0.2732 0.4616 0.046 Uiso 1 1 calc R . .
H28C H 0.4561 0.2753 0.5873 0.046 Uiso 1 1 calc R . .
C29 C 0.7003(3) 0.37859(18) 0.4813(3) 0.0330(6) Uani 1 1 d . . .
H29A H 0.7036 0.3220 0.5130 0.040 Uiso 1 1 calc R . .
H29B H 0.7876 0.4052 0.5212 0.040 Uiso 1 1 calc R . .
C30 C 0.6981(4) 0.3801(2) 0.3220(4) 0.0578(10) Uani 1 1 d . . .
H30A H 0.6159 0.3502 0.2814 0.087 Uiso 1 1 calc R . .
H30B H 0.7844 0.3553 0.2932 0.087 Uiso 1 1 calc R . .
H30C H 0.6924 0.4359 0.2892 0.087 Uiso 1 1 calc R . .
C31 C 0.5678(3) 0.50728(16) 0.4968(3) 0.0379(7) Uani 1 1 d . . .
H31A H 0.5576 0.5106 0.3934 0.045 Uiso 1 1 calc R . .
H31B H 0.4817 0.5309 0.5314 0.045 Uiso 1 1 calc R . .
C32 C 0.6918(3) 0.55757(17) 0.5495(3) 0.0379(6) Uani 1 1 d . . .
H32A H 0.7000 0.5576 0.6520 0.057 Uiso 1 1 calc R . .
H32B H 0.6785 0.6127 0.5152 0.057 Uiso 1 1 calc R . .
H32C H 0.7780 0.5352 0.5157 0.057 Uiso 1 1 calc R . .
C1E C 0.8863(4) 0.2931(2) 0.8876(3) 0.0464(8) Uani 1 1 d . . .
H1E1 H 0.8709 0.3271 0.8044 0.070 Uiso 1 1 calc R . .
H1E2 H 0.8430 0.2404 0.8685 0.070 Uiso 1 1 calc R . .
H1E3 H 0.9878 0.2865 0.9115 0.070 Uiso 1 1 calc R . .
C2E C 0.8207(3) 0.33191(19) 1.0077(3) 0.0424(7) Uani 1 1 d . . .
H2E1 H 0.7187 0.3399 0.9821 0.051 Uiso 1 1 calc R . .
H2E2 H 0.8307 0.2956 1.0897 0.051 Uiso 1 1 calc R . .
F1 F 0.61421(15) 0.14902(10) 0.75112(15) 0.0302(3) Uani 1 1 d . . .
N1 N 0.5747(2) 0.41936(12) 0.5381(2) 0.0242(4) Uani 1 1 d . . .
O1 O -0.22739(16) 0.03029(9) 0.66827(16) 0.0189(3) Uani 1 1 d . . .
H1 H -0.2637 0.0663 0.7149 0.028 Uiso 1 1 calc R . .
O2 O -0.04272(18) -0.06522(10) 0.51670(18) 0.0260(4) Uani 1 1 d . . .
O3 O -0.34289(16) 0.15238(10) 0.49068(16) 0.0207(3) Uani 1 1 d . . .
H3 H -0.3552 0.1547 0.5762 0.031 Uiso 1 1 calc R . .
O4 O -0.11654(16) 0.20379(9) 0.49609(15) 0.0182(3) Uani 1 1 d . . .
O5 O 0.30316(16) 0.26103(9) 0.79593(15) 0.0191(3) Uani 1 1 d . . .
O6 O 0.50419(16) 0.23505(10) 0.94052(17) 0.0222(3) Uani 1 1 d . . .
H6 H 0.5464 0.2064 0.8853 0.033 Uiso 1 1 calc R . .
O7 O 0.22826(19) 0.04476(10) 1.09014(17) 0.0257(4) Uani 1 1 d . . .
O8 O 0.41762(17) 0.07196(10) 0.88342(18) 0.0235(3) Uani 1 1 d . . .
H8A H 0.4759 0.0917 0.8319 0.035 Uiso 1 1 calc R . .
O1E O 0.8833(3) 0.40664(13) 1.0446(3) 0.0482(5) Uani 1 1 d . . .
H1E H 0.8414 0.4432 0.9973 0.072 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
C1 C2 1.385(3) . ?
C1 C24 1.388(3) . ?
C1 H1A 0.9500 . ?
C2 C12 1.397(3) . ?
C2 C3 1.498(3) . ?
C3 O1 1.409(2) . ?
C3 C4 1.547(3) . ?
C3 C11 1.582(3) . ?
C4 O2 1.211(3) . ?
C4 C5 1.476(3) . ?
C5 C10 1.384(3) . ?
C5 C6 1.391(3) . ?
C6 C7 1.383(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.395(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.504(3) . ?
C11 O3 1.368(3) . ?
C11 O4 1.476(3) . ?
C12 O4 1.362(2) . ?
C12 C13 1.386(3) . ?
C13 C14 1.383(3) . ?
C13 H13 0.9500 . ?
C14 O5 1.370(2) . ?
C14 C24 1.396(3) . ?
C15 O6 1.363(3) . ?
C15 O5 1.469(3) . ?
C15 C16 1.514(3) . ?
C15 C23 1.579(3) . ?
C16 C17 1.387(3) . ?
C16 C21 1.392(3) . ?
C17 C18 1.387(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.394(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.476(3) . ?
C22 O7 1.207(3) . ?
C22 C23 1.540(3) . ?
C23 O8 1.403(3) . ?
C23 C24 1.516(3) . ?
C25 C26 1.514(4) . ?
C25 N1 1.529(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 N1 1.511(3) . ?
C27 C28 1.515(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 N1 1.515(3) . ?
C29 C30 1.527(5) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.500(4) . ?
C31 N1 1.517(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C1E C2E 1.502(4) . ?
C1E H1E1 0.9800 . ?
C1E H1E2 0.9800 . ?
C1E H1E3 0.9800 . ?
C2E O1E 1.412(4) . ?
C2E H2E1 0.9900 . ?
C2E H2E2 0.9900 . ?
O1 H1 0.8400 . ?
O3 H3 0.8400 . ?
O6 H6 0.8400 . ?
O8 H8A 0.8400 . ?
O1E H1E 0.8400 . ?

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 C24 117.19(19) . . ?
C2 C1 H1A 121.4 . . ?
C24 C1 H1A 121.4 . . ?
C1 C2 C12 120.80(19) . . ?
C1 C2 C3 130.18(19) . . ?
C12 C2 C3 108.98(17) . . ?
O1 C3 C2 116.01(16) . . ?
O1 C3 C4 107.37(16) . . ?
C2 C3 C4 110.72(16) . . ?
O1 C3 C11 115.58(16) . . ?
C2 C3 C11 102.60(16) . . ?
C4 C3 C11 103.90(16) . . ?
O2 C4 C5 127.3(2) . . ?
O2 C4 C3 124.3(2) . . ?
C5 C4 C3 108.31(17) . . ?
C10 C5 C6 121.5(2) . . ?
C10 C5 C4 110.24(19) . . ?
C6 C5 C4 128.2(2) . . ?
C7 C6 C5 118.0(2) . . ?
C7 C6 H6A 121.0 . . ?
C5 C6 H6A 121.0 . . ?
C6 C7 C8 120.3(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 121.9(2) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 117.6(2) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 H9 121.2 . . ?
C5 C10 C9 120.6(2) . . ?
C5 C10 C11 112.12(18) . . ?
C9 C10 C11 127.3(2) . . ?
O3 C11 O4 108.87(17) . . ?
O3 C11 C10 111.04(17) . . ?
O4 C11 C10 108.38(16) . . ?
O3 C11 C3 117.16(17) . . ?
O4 C11 C3 105.84(15) . . ?
C10 C11 C3 105.13(16) . . ?
O4 C12 C13 122.82(19) . . ?
O4 C12 C2 113.80(18) . . ?
C13 C12 C2 123.35(19) . . ?
C14 C13 C12 114.42(19) . . ?
C14 C13 H13 122.8 . . ?
C12 C13 H13 122.8 . . ?
O5 C14 C13 123.13(19) . . ?
O5 C14 C24 113.07(18) . . ?
C13 C14 C24 123.80(19) . . ?
O6 C15 O5 109.13(17) . . ?
O6 C15 C16 112.07(17) . . ?
O5 C15 C16 107.25(17) . . ?
O6 C15 C23 117.82(18) . . ?
O5 C15 C23 106.03(16) . . ?
C16 C15 C23 103.89(17) . . ?
C17 C16 C21 120.4(2) . . ?
C17 C16 C15 128.0(2) . . ?
C21 C16 C15 111.50(19) . . ?
C16 C17 C18 118.2(2) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C17 C18 C19 121.4(2) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C20 C19 C18 120.9(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 117.5(2) . . ?
C19 C20 H20 121.3 . . ?
C21 C20 H20 121.3 . . ?
C16 C21 C20 121.7(2) . . ?
C16 C21 C22 110.19(19) . . ?
C20 C21 C22 128.1(2) . . ?
O7 C22 C21 127.5(2) . . ?
O7 C22 C23 125.5(2) . . ?
C21 C22 C23 106.95(18) . . ?
O8 C23 C24 115.83(17) . . ?
O8 C23 C22 109.70(17) . . ?
C24 C23 C22 107.99(16) . . ?
O8 C23 C15 117.55(17) . . ?
C24 C23 C15 100.64(17) . . ?
C22 C23 C15 104.05(16) . . ?
C1 C24 C14 120.43(19) . . ?
C1 C24 C23 130.33(19) . . ?
C14 C24 C23 109.16(18) . . ?
C26 C25 N1 115.2(2) . . ?
C26 C25 H25A 108.5 . . ?
N1 C25 H25A 108.5 . . ?
C26 C25 H25B 108.5 . . ?
N1 C25 H25B 108.5 . . ?
H25A C25 H25B 107.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N1 C27 C28 115.2(2) . . ?
N1 C27 H27A 108.5 . . ?
C28 C27 H27A 108.5 . . ?
N1 C27 H27B 108.5 . . ?
C28 C27 H27B 108.5 . . ?
H27A C27 H27B 107.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N1 C29 C30 114.0(3) . . ?
N1 C29 H29A 108.7 . . ?
C30 C29 H29A 108.7 . . ?
N1 C29 H29B 108.7 . . ?
C30 C29 H29B 108.7 . . ?
H29A C29 H29B 107.6 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 N1 115.8(2) . . ?
C32 C31 H31A 108.3 . . ?
N1 C31 H31A 108.3 . . ?
C32 C31 H31B 108.3 . . ?
N1 C31 H31B 108.3 . . ?
H31A C31 H31B 107.4 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C2E C1E H1E1 109.5 . . ?
C2E C1E H1E2 109.5 . . ?
H1E1 C1E H1E2 109.5 . . ?
C2E C1E H1E3 109.5 . . ?
H1E1 C1E H1E3 109.5 . . ?
H1E2 C1E H1E3 109.5 . . ?
O1E C2E C1E 112.2(3) . . ?
O1E C2E H2E1 109.2 . . ?
C1E C2E H2E1 109.2 . . ?
O1E C2E H2E2 109.2 . . ?
C1E C2E H2E2 109.2 . . ?
H2E1 C2E H2E2 107.9 . . ?
C27 N1 C29 111.0(2) . . ?
C27 N1 C31 106.34(19) . . ?
C29 N1 C31 110.9(2) . . ?
C27 N1 C25 111.4(2) . . ?
C29 N1 C25 105.79(19) . . ?
C31 N1 C25 111.4(2) . . ?
C3 O1 H1 109.5 . . ?
C11 O3 H3 109.5 . . ?
C12 O4 C11 108.74(15) . . ?
C14 O5 C15 107.56(16) . . ?
C15 O6 H6 109.5 . . ?
C23 O8 H8A 109.5 . . ?
C2E O1E H1E 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H6 F1 0.84 1.77 2.602(2) 171.6 .
O8 H8A F1 0.84 1.85 2.675(2) 167.7 .
O1 H1 F1 0.84 1.85 2.648(2) 157.4 1_455
O3 H3 F1 0.84 1.73 2.567(2) 173.9 1_455
O1E H1E O7 0.84 1.98 2.803(3) 167.6 2_657

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        28.04
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.059
