# Electronic Supplementary Material (ESI) for Molecular Systems Design & Engineering.
# 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_Acet5
_database_code_depnum_ccdc_archive 'CCDC 1498067'
_audit_update_record             
;
2016-08-08 deposited with the CCDC.
2016-09-09 downloaded from the CCDC.
;

_audit_creation_date             2013-04-22T14:25:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 5-carboxyfluorescein diacetate monohydrate
;
_chemical_formula_moiety         'C25 H16 O9, O1'
_chemical_formula_sum            'C25 H16 O10'
_chemical_formula_analytical     ?
_chemical_formula_weight         476.38

#==============================================================================

# CRYSTAL DATA

_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                   9.152(5)
_cell_length_b                   11.320(6)
_cell_length_c                   11.643(7)
_cell_angle_alpha                98.572(8)
_cell_angle_beta                 106.510(8)
_cell_angle_gamma                90.612(6)
_cell_volume                     1141.8(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3208
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      33.2
_cell_measurement_temperature    120(2)
_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Higashi, 1995'
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.981

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
        Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            6479
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total             3907
_reflns_number_gt                3516
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.062
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1602
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_number_reflns         3907
_refine_ls_number_parameters     340
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0851P)²+0.7585P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 1.2464(2) 0.49676(19) 0.0955(2) 0.0290(5) Uani d . 1 . . C
C2 1.2592(3) 0.5142(2) 0.2184(2) 0.0362(5) Uani d . 1 . . C
H2 1.3144 0.4634 0.2686 0.043 Uiso calc R 1 . . H
C3 1.1878(3) 0.6091(2) 0.2645(2) 0.0355(5) Uani d . 1 . . C
H3 1.1954 0.6219 0.3469 0.043 Uiso calc R 1 . . H
C4 1.1044(2) 0.68662(19) 0.19049(19) 0.0276(5) Uani d . 1 . . C
C5 1.0967(2) 0.66661(18) 0.06888(19) 0.0258(4) Uani d . 1 . . C
C6 1.1684(2) 0.57191(19) 0.02019(19) 0.0287(5) Uani d . 1 . . C
H6 1.1635 0.56 -0.0616 0.034 Uiso calc R 1 . . H
C7 1.4541(3) 0.3831(2) 0.0678(2) 0.0382(6) Uani d . 1 . . C
C8 1.4907(3) 0.2710(2) 0.0009(2) 0.0378(6) Uani d . 1 . . C
H8A 1.5995 0.2665 0.0199 0.057 Uiso calc R 1 . . H
H8B 1.4484 0.27 -0.0847 0.057 Uiso calc R 1 . . H
H8C 1.4481 0.2037 0.0242 0.057 Uiso calc R 1 . . H
C9 0.7771(2) 0.98369(19) -0.0335(2) 0.0288(5) Uani d . 1 . . C
C10 0.7750(2) 1.0181(2) 0.0851(2) 0.0312(5) Uani d . 1 . . C
H10 0.7213 1.0834 0.1052 0.037 Uiso calc R 1 . . H
C11 0.8540(2) 0.95408(19) 0.1733(2) 0.0301(5) Uani d . 1 . . C
H11 0.8515 0.976 0.2529 0.036 Uiso calc R 1 . . H
C12 0.9377(2) 0.85698(18) 0.14484(19) 0.0265(5) Uani d . 1 . . C
C13 0.9378(2) 0.82665(18) 0.02503(19) 0.0263(4) Uani d . 1 . . C
C14 0.8566(2) 0.88860(18) -0.06572(19) 0.0273(5) Uani d . 1 . . C
H14 0.8565 0.866 -0.1459 0.033 Uiso calc R 1 . . H
C15 0.5721(2) 1.0063(2) -0.2053(2) 0.0324(5) Uani d . 1 . . C
C16 0.5206(3) 1.0820(2) -0.3022(2) 0.0428(6) Uani d . 1 . . C
H16A 0.5703 1.0599 -0.364 0.064 Uiso calc R 1 . . H
H16B 0.5462 1.1647 -0.2679 0.064 Uiso calc R 1 . . H
H16C 0.412 1.0701 -0.3372 0.064 Uiso calc R 1 . . H
C17 1.0228(2) 0.78677(19) 0.24169(18) 0.0270(5) Uani d . 1 . . C
C18 0.9207(2) 0.74573(18) 0.31233(19) 0.0276(5) Uani d . 1 . . C
C19 0.9681(3) 0.80478(19) 0.43045(19) 0.0300(5) Uani d . 1 . . C
C20 0.8869(3) 0.7924(2) 0.51197(19) 0.0327(5) Uani d . 1 . . C
H20 0.9195 0.8327 0.5913 0.039 Uiso calc R 1 . . H
C21 0.7552(3) 0.7180(2) 0.47153(19) 0.0318(5) Uani d . 1 . . C
C22 0.7107(3) 0.65436(19) 0.3540(2) 0.0312(5) Uani d . 1 . . C
H22 0.624 0.6027 0.3293 0.037 Uiso calc R 1 . . H
C23 0.7934(3) 0.66683(19) 0.27301(19) 0.0298(5) Uani d . 1 . . C
H23 0.7643 0.6236 0.1949 0.036 Uiso calc R 1 . . H
C24 1.1060(3) 0.8806(2) 0.44548(19) 0.0311(5) Uani d . 1 . . C
C25 0.6603(3) 0.7129(2) 0.5553(2) 0.0374(5) Uani d . 1 . . C
O1 1.30215(17) 0.39533(13) 0.04088(14) 0.0331(4) Uani d . 1 . . O
O2 1.5432(2) 0.4557(3) 0.1366(3) 0.0998(11) Uani d . 1 . . O
O3 0.70456(17) 1.05373(13) -0.12206(14) 0.0329(4) Uani d . 1 . . O
O4 0.50831(19) 0.91563(15) -0.19745(16) 0.0413(4) Uani d . 1 . . O
O5 1.01706(17) 0.73465(13) -0.01400(13) 0.0295(4) Uani d . 1 . . O
O6 1.13702(17) 0.86960(13) 0.33651(13) 0.0300(4) Uani d . 1 . . O
O7 1.18501(19) 0.94416(15) 0.53361(14) 0.0387(4) Uani d . 1 . . O
O8 0.5300(2) 0.6490(2) 0.50530(17) 0.0552(6) Uani d . 1 . . O
H8O 0.4813 0.6511 0.5547 0.083 Uiso calc R 1 . . H
O9 0.6969(2) 0.7625(2) 0.65857(16) 0.0600(6) Uani d . 1 . . O
O10A 0.3413(15) 0.7023(7) 0.6417(10) 0.0397(19) Uani d P 0.57(3) A 1 O
O10B 0.402(3) 0.6837(10) 0.6799(18) 0.029(4) Uani d P 0.26(3) B 2 O
O10C 0.2423(10) 0.6784(6) 0.6735(7) 0.021(3) Uani d P 0.170(6) C 3 O



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.372(3) ?
C1 C2 . 1.386(3) ?
C1 O1 . 1.401(3) ?
C2 C3 . 1.383(3) ?
C2 H2 . 0.93 ?
C3 C4 . 1.400(3) ?
C3 H3 . 0.93 ?
C4 C5 . 1.381(3) ?
C4 C17 . 1.506(3) ?
C5 O5 . 1.374(3) ?
C5 C6 . 1.395(3) ?
C6 H6 . 0.93 ?
C7 O2 . 1.183(3) ?
C7 O1 . 1.350(3) ?
C7 C8 . 1.481(3) ?
C8 H8A . 0.96 ?
C8 H8B . 0.96 ?
C8 H8C . 0.96 ?
C9 C14 . 1.372(3) ?
C9 C10 . 1.383(3) ?
C9 O3 . 1.414(3) ?
C10 C11 . 1.383(3) ?
C10 H10 . 0.93 ?
C11 C12 . 1.399(3) ?
C11 H11 . 0.93 ?
C12 C13 . 1.386(3) ?
C12 C17 . 1.514(3) ?
C13 O5 . 1.371(3) ?
C13 C14 . 1.395(3) ?
C14 H14 . 0.93 ?
C15 O4 . 1.203(3) ?
C15 O3 . 1.364(3) ?
C15 C16 . 1.492(3) ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 O6 . 1.485(2) ?
C17 C18 . 1.519(3) ?
C18 C19 . 1.381(3) ?
C18 C23 . 1.384(3) ?
C19 C20 . 1.382(3) ?
C19 C24 . 1.473(3) ?
C20 C21 . 1.386(3) ?
C20 H20 . 0.93 ?
C21 C22 . 1.393(3) ?
C21 C25 . 1.486(3) ?
C22 C23 . 1.387(3) ?
C22 H22 . 0.93 ?
C23 H23 . 0.93 ?
C24 O7 . 1.200(3) ?
C24 O6 . 1.365(3) ?
C25 O9 . 1.199(3) ?
C25 O8 . 1.321(3) ?
O8 H8O . 0.82 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.0(2) . . ?
C6 C1 O1 116.82(19) . . ?
C2 C1 O1 120.97(19) . . ?
C3 C2 C1 118.2(2) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.7(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 117.9(2) . . ?
C5 C4 C17 121.21(19) . . ?
C3 C4 C17 120.83(19) . . ?
O5 C5 C4 123.93(19) . . ?
O5 C5 C6 114.56(18) . . ?
C4 C5 C6 121.5(2) . . ?
C1 C6 C5 118.6(2) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
O2 C7 O1 122.1(2) . . ?
O2 C7 C8 126.2(2) . . ?
O1 C7 C8 111.7(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 121.8(2) . . ?
C14 C9 O3 119.05(19) . . ?
C10 C9 O3 119.00(19) . . ?
C9 C10 C11 119.1(2) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C10 C11 C12 121.2(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 117.68(19) . . ?
C13 C12 C17 121.46(19) . . ?
C11 C12 C17 120.86(19) . . ?
O5 C13 C12 123.29(19) . . ?
O5 C13 C14 114.64(18) . . ?
C12 C13 C14 122.07(19) . . ?
C9 C14 C13 118.2(2) . . ?
C9 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
O4 C15 O3 122.6(2) . . ?
O4 C15 C16 126.5(2) . . ?
O3 C15 C16 111.0(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O6 C17 C4 108.85(16) . . ?
O6 C17 C12 108.38(16) . . ?
C4 C17 C12 111.59(18) . . ?
O6 C17 C18 102.28(16) . . ?
C4 C17 C18 113.29(18) . . ?
C12 C17 C18 111.89(17) . . ?
C19 C18 C23 120.8(2) . . ?
C19 C18 C17 109.52(19) . . ?
C23 C18 C17 129.61(19) . . ?
C18 C19 C20 121.7(2) . . ?
C18 C19 C24 108.4(2) . . ?
C20 C19 C24 129.9(2) . . ?
C19 C20 C21 117.8(2) . . ?
C19 C20 H20 121.1 . . ?
C21 C20 H20 121.1 . . ?
C20 C21 C22 120.6(2) . . ?
C20 C21 C25 117.9(2) . . ?
C22 C21 C25 121.4(2) . . ?
C23 C22 C21 121.1(2) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C18 C23 C22 117.8(2) . . ?
C18 C23 H23 121.1 . . ?
C22 C23 H23 121.1 . . ?
O7 C24 O6 121.4(2) . . ?
O7 C24 C19 130.1(2) . . ?
O6 C24 C19 108.41(18) . . ?
O9 C25 O8 122.7(2) . . ?
O9 C25 C21 123.6(2) . . ?
O8 C25 C21 113.7(2) . . ?
C7 O1 C1 119.60(17) . . ?
C15 O3 C9 117.11(17) . . ?
C13 O5 C5 118.49(17) . . ?
C24 O6 C17 111.31(16) . . ?
C25 O8 H8O 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.4(3) . . . . ?
O1 C1 C2 C3 -173.2(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C2 C3 C4 C17 177.8(2) . . . . ?
C3 C4 C5 O5 179.03(19) . . . . ?
C17 C4 C5 O5 0.4(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C17 C4 C5 C6 -178.15(19) . . . . ?
C2 C1 C6 C5 -1.8(3) . . . . ?
O1 C1 C6 C5 173.06(18) . . . . ?
O5 C5 C6 C1 -177.88(18) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C14 C9 C10 C11 -0.7(3) . . . . ?
O3 C9 C10 C11 -175.97(18) . . . . ?
C9 C10 C11 C12 1.2(3) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C10 C11 C12 C17 -179.53(19) . . . . ?
C11 C12 C13 O5 178.99(19) . . . . ?
C17 C12 C13 O5 -1.9(3) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C17 C12 C13 C14 178.29(18) . . . . ?
C10 C9 C14 C13 -0.4(3) . . . . ?
O3 C9 C14 C13 174.79(17) . . . . ?
O5 C13 C14 C9 -178.58(18) . . . . ?
C12 C13 C14 C9 1.2(3) . . . . ?
C5 C4 C17 O6 -119.8(2) . . . . ?
C3 C4 C17 O6 61.7(3) . . . . ?
C5 C4 C17 C12 -0.2(3) . . . . ?
C3 C4 C17 C12 -178.76(19) . . . . ?
C5 C4 C17 C18 127.2(2) . . . . ?
C3 C4 C17 C18 -51.4(3) . . . . ?
C13 C12 C17 O6 120.8(2) . . . . ?
C11 C12 C17 O6 -60.2(2) . . . . ?
C13 C12 C17 C4 0.9(3) . . . . ?
C11 C12 C17 C4 179.98(18) . . . . ?
C13 C12 C17 C18 -127.2(2) . . . . ?
C11 C12 C17 C18 51.9(3) . . . . ?
O6 C17 C18 C19 3.2(2) . . . . ?
C4 C17 C18 C19 120.20(19) . . . . ?
C12 C17 C18 C19 -112.6(2) . . . . ?
O6 C17 C18 C23 -179.7(2) . . . . ?
C4 C17 C18 C23 -62.7(3) . . . . ?
C12 C17 C18 C23 64.5(3) . . . . ?
C23 C18 C19 C20 -3.3(3) . . . . ?
C17 C18 C19 C20 174.13(19) . . . . ?
C23 C18 C19 C24 179.34(19) . . . . ?
C17 C18 C19 C24 -3.2(2) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C24 C19 C20 C21 176.9(2) . . . . ?
C19 C20 C21 C22 2.6(3) . . . . ?
C19 C20 C21 C25 -174.6(2) . . . . ?
C20 C21 C22 C23 -2.3(3) . . . . ?
C25 C21 C22 C23 174.8(2) . . . . ?
C19 C18 C23 C22 3.5(3) . . . . ?
C17 C18 C23 C22 -173.3(2) . . . . ?
C21 C22 C23 C18 -0.8(3) . . . . ?
C18 C19 C24 O7 -178.2(2) . . . . ?
C20 C19 C24 O7 4.7(4) . . . . ?
C18 C19 C24 O6 1.9(2) . . . . ?
C20 C19 C24 O6 -175.1(2) . . . . ?
C20 C21 C25 O9 -5.7(4) . . . . ?
C22 C21 C25 O9 177.1(2) . . . . ?
C20 C21 C25 O8 173.8(2) . . . . ?
C22 C21 C25 O8 -3.4(3) . . . . ?
O2 C7 O1 C1 0.0(4) . . . . ?
C8 C7 O1 C1 -179.7(2) . . . . ?
C6 C1 O1 C7 116.2(2) . . . . ?
C2 C1 O1 C7 -68.9(3) . . . . ?
O4 C15 O3 C9 8.3(3) . . . . ?
C16 C15 O3 C9 -172.17(19) . . . . ?
C14 C9 O3 C15 76.2(3) . . . . ?
C10 C9 O3 C15 -108.5(2) . . . . ?
C12 C13 O5 C5 2.1(3) . . . . ?
C14 C13 O5 C5 -178.13(17) . . . . ?
C4 C5 O5 C13 -1.3(3) . . . . ?
C6 C5 O5 C13 177.37(17) . . . . ?
O7 C24 O6 C17 -179.7(2) . . . . ?
C19 C24 O6 C17 0.2(2) . . . . ?
C4 C17 O6 C24 -122.15(18) . . . . ?
C12 C17 O6 C24 116.30(19) . . . . ?
C18 C17 O6 C24 -2.0(2) . . . . ?


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

data_Acet6
_database_code_depnum_ccdc_archive 'CCDC 1498068'
_audit_update_record             
;
2016-08-08 deposited with the CCDC.
2016-09-09 downloaded from the CCDC.
;

_audit_creation_date             2013-04-22T14:38:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 6-carboxyfluorescein diacetate monohydrate
;
_chemical_formula_moiety         'C25 H16 O9, O1'
_chemical_formula_sum            'C25 H16 O10'
_chemical_formula_analytical     ?
_chemical_formula_weight         476.38

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   9.278(3)
_cell_length_b                   11.599(3)
_cell_length_c                   21.066(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.606(4)
_cell_angle_gamma                90
_cell_volume                     2241.5(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5660
_cell_measurement_theta_min      2
_cell_measurement_theta_max      32.9
_cell_measurement_temperature    120(2)
_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Higashi, 1995'
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.988

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
        Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            11551
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total             5073
_reflns_number_gt                4511
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1503
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.08
_refine_ls_number_reflns         5073
_refine_ls_number_parameters     340
_refine_ls_number_restraints     7
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0698P)²+1.5545P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.51384(18) 0.45056(16) 0.36799(8) 0.0219(4) Uani d . 1 . . C
C2 0.54409(19) 0.33423(16) 0.37730(9) 0.0238(4) Uani d . 1 . . C
H2 0.608 0.2967 0.3542 0.029 Uiso calc R 1 . . H
C3 0.47667(19) 0.27524(15) 0.42194(9) 0.0232(4) Uani d . 1 . . C
H3 0.4944 0.1968 0.4282 0.028 Uiso calc R 1 . . H
C4 0.38239(18) 0.33127(15) 0.45785(8) 0.0199(3) Uani d . 1 . . C
C5 0.35784(18) 0.44874(15) 0.44764(8) 0.0201(3) Uani d . 1 . . C
C6 0.42274(19) 0.50967(16) 0.40251(8) 0.0226(4) Uani d . 1 . . C
H6 0.4051 0.588 0.3959 0.027 Uiso calc R 1 . . H
C7 0.5212(2) 0.52270(16) 0.26398(9) 0.0248(4) Uani d . 1 . . C
C8 0.6071(2) 0.5957(2) 0.22549(10) 0.0329(4) Uani d . 1 . . C
H8A 0.5776 0.5803 0.1807 0.049 Uiso calc R 1 . . H
H8B 0.7089 0.5785 0.2369 0.049 Uiso calc R 1 . . H
H8C 0.5905 0.6755 0.234 0.049 Uiso calc R 1 . . H
C9 0.05876(19) 0.48773(15) 0.61043(8) 0.0216(4) Uani d . 1 . . C
C10 0.0709(2) 0.37120(16) 0.62687(9) 0.0248(4) Uani d . 1 . . C
H10 0.024 0.341 0.6592 0.03 Uiso calc R 1 . . H
C11 0.1551(2) 0.30220(15) 0.59342(9) 0.0231(4) Uani d . 1 . . C
H11 0.1663 0.2247 0.6045 0.028 Uiso calc R 1 . . H
C12 0.22421(18) 0.34450(15) 0.54358(8) 0.0196(3) Uani d . 1 . . C
C13 0.20847(18) 0.46068(15) 0.52885(8) 0.0199(3) Uani d . 1 . . C
C14 0.12711(19) 0.53332(16) 0.56235(8) 0.0222(4) Uani d . 1 . . C
H14 0.119 0.6114 0.5525 0.027 Uiso calc R 1 . . H
C15 -0.0325(2) 0.56798(17) 0.70269(9) 0.0259(4) Uani d . 1 . . C
C16 -0.1237(2) 0.66741(17) 0.71829(10) 0.0290(4) Uani d . 1 . . C
H16A -0.1337 0.665 0.763 0.044 Uiso calc R 1 . . H
H16B -0.2183 0.6627 0.6928 0.044 Uiso calc R 1 . . H
H16C -0.0776 0.7384 0.7092 0.044 Uiso calc R 1 . . H
C17 0.30698(18) 0.26510(15) 0.50522(8) 0.0195(3) Uani d . 1 . . C
C18 0.21338(18) 0.16761(15) 0.47381(8) 0.0194(3) Uani d . 1 . . C
C19 0.08825(18) 0.17304(15) 0.42857(8) 0.0201(3) Uani d . 1 . . C
H19 0.05 0.2434 0.413 0.024 Uiso calc R 1 . . H
C20 0.02225(18) 0.06959(15) 0.40740(8) 0.0207(3) Uani d . 1 . . C
C21 0.0813(2) -0.03684(16) 0.42986(9) 0.0236(4) Uani d . 1 . . C
H21 0.0363 -0.1049 0.4142 0.028 Uiso calc R 1 . . H
C22 0.20594(19) -0.04134(15) 0.47506(9) 0.0228(4) Uani d . 1 . . C
H22 0.246 -0.1113 0.4904 0.027 Uiso calc R 1 . . H
C23 0.26871(18) 0.06282(15) 0.49662(8) 0.0196(3) Uani d . 1 . . C
C24 0.39858(18) 0.08556(15) 0.54499(8) 0.0197(3) Uani d . 1 . . C
C25 -0.11648(19) 0.07695(16) 0.36064(8) 0.0224(4) Uani d . 1 . . C
O1 0.58701(14) 0.51276(12) 0.32526(6) 0.0252(3) Uani d . 1 . . O
O2 0.40584(15) 0.47698(14) 0.24568(7) 0.0331(3) Uani d . 1 . . O
O3 -0.02956(14) 0.56536(11) 0.63783(6) 0.0248(3) Uani d . 1 . . O
O4 0.03119(19) 0.50106(14) 0.73973(7) 0.0406(4) Uani d . 1 . . O
O5 0.26940(14) 0.51340(11) 0.48063(6) 0.0229(3) Uani d . 1 . . O
O6 0.41847(13) 0.20193(10) 0.54966(6) 0.0212(3) Uani d . 1 . . O
O7 0.47838(14) 0.01875(11) 0.57689(6) 0.0249(3) Uani d . 1 . . O
O8 -0.15884(15) 0.16624(12) 0.33436(7) 0.0312(3) Uani d . 1 . . O
O9 -0.18829(14) -0.02194(11) 0.35228(6) 0.0252(3) Uani d . 1 . . O
H9 -0.2612 -0.0134 0.3254 0.038 Uiso calc R 1 . . H
O10 0.2955(4) 0.7976(3) 0.3140(2) 0.0482(17) Uani d P 0.432(6) A 1 O
O11 0.2242(4) 0.6994(3) 0.30329(16) 0.0287(12) Uani d P 0.359(5) B 2 O
O12 0.3464(6) 0.7525(8) 0.2765(3) 0.044(3) Uani d PU 0.211(6) C 3 O



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.377(3) ?
C1 C2 . 1.386(3) ?
C1 O1 . 1.405(2) ?
C2 C3 . 1.385(3) ?
C2 H2 . 0.93 ?
C3 C4 . 1.399(2) ?
C3 H3 . 0.93 ?
C4 C5 . 1.393(2) ?
C4 C17 . 1.511(2) ?
C5 O5 . 1.375(2) ?
C5 C6 . 1.392(2) ?
C6 H6 . 0.93 ?
C7 O2 . 1.205(2) ?
C7 O1 . 1.348(2) ?
C7 C8 . 1.485(3) ?
C8 H8A . 0.96 ?
C8 H8B . 0.96 ?
C8 H8C . 0.96 ?
C9 C14 . 1.378(3) ?
C9 C10 . 1.396(3) ?
C9 O3 . 1.399(2) ?
C10 C11 . 1.383(3) ?
C10 H10 . 0.93 ?
C11 C12 . 1.398(2) ?
C11 H11 . 0.93 ?
C12 C13 . 1.386(2) ?
C12 C17 . 1.509(2) ?
C13 O5 . 1.377(2) ?
C13 C14 . 1.392(2) ?
C14 H14 . 0.93 ?
C15 O4 . 1.192(2) ?
C15 O3 . 1.371(2) ?
C15 C16 . 1.496(3) ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 O6 . 1.481(2) ?
C17 C18 . 1.516(2) ?
C18 C23 . 1.378(2) ?
C18 C19 . 1.389(2) ?
C19 C20 . 1.390(2) ?
C19 H19 . 0.93 ?
C20 C21 . 1.404(2) ?
C20 C25 . 1.502(2) ?
C21 C22 . 1.384(2) ?
C21 H21 . 0.93 ?
C22 C23 . 1.388(2) ?
C22 H22 . 0.93 ?
C23 C24 . 1.481(2) ?
C24 O7 . 1.205(2) ?
C24 O6 . 1.364(2) ?
C25 O8 . 1.212(2) ?
C25 O9 . 1.325(2) ?
O9 H9 . 0.82 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.49(17) . . ?
C6 C1 O1 118.43(16) . . ?
C2 C1 O1 118.90(16) . . ?
C3 C2 C1 118.31(17) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 121.32(17) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 118.15(16) . . ?
C5 C4 C17 121.18(15) . . ?
C3 C4 C17 120.65(15) . . ?
O5 C5 C6 114.86(15) . . ?
O5 C5 C4 123.49(15) . . ?
C6 C5 C4 121.65(16) . . ?
C1 C6 C5 118.05(17) . . ?
C1 C6 H6 121 . . ?
C5 C6 H6 121 . . ?
O2 C7 O1 121.49(17) . . ?
O2 C7 C8 126.89(17) . . ?
O1 C7 C8 111.61(16) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 121.66(17) . . ?
C14 C9 O3 114.74(16) . . ?
C10 C9 O3 123.47(16) . . ?
C11 C10 C9 117.70(17) . . ?
C11 C10 H10 121.1 . . ?
C9 C10 H10 121.1 . . ?
C10 C11 C12 122.48(17) . . ?
C10 C11 H11 118.8 . . ?
C12 C11 H11 118.8 . . ?
C13 C12 C11 117.69(16) . . ?
C13 C12 C17 121.25(15) . . ?
C11 C12 C17 121.00(15) . . ?
O5 C13 C12 123.77(16) . . ?
O5 C13 C14 114.76(15) . . ?
C12 C13 C14 121.47(16) . . ?
C9 C14 C13 118.98(17) . . ?
C9 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
O4 C15 O3 123.78(18) . . ?
O4 C15 C16 126.81(18) . . ?
O3 C15 C16 109.40(16) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O6 C17 C12 109.08(13) . . ?
O6 C17 C4 108.67(13) . . ?
C12 C17 C4 111.51(14) . . ?
O6 C17 C18 101.96(13) . . ?
C12 C17 C18 112.63(14) . . ?
C4 C17 C18 112.47(14) . . ?
C23 C18 C19 120.60(16) . . ?
C23 C18 C17 110.28(14) . . ?
C19 C18 C17 129.12(16) . . ?
C18 C19 C20 117.63(16) . . ?
C18 C19 H19 121.2 . . ?
C20 C19 H19 121.2 . . ?
C19 C20 C21 121.34(15) . . ?
C19 C20 C25 117.04(15) . . ?
C21 C20 C25 121.61(16) . . ?
C22 C21 C20 120.57(17) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 117.31(16) . . ?
C21 C22 H22 121.3 . . ?
C23 C22 H22 121.3 . . ?
C18 C23 C22 122.52(15) . . ?
C18 C23 C24 107.78(15) . . ?
C22 C23 C24 129.70(16) . . ?
O7 C24 O6 122.08(16) . . ?
O7 C24 C23 129.66(16) . . ?
O6 C24 C23 108.26(14) . . ?
O8 C25 O9 123.84(16) . . ?
O8 C25 C20 122.40(16) . . ?
O9 C25 C20 113.74(15) . . ?
C7 O1 C1 117.66(14) . . ?
C15 O3 C9 121.70(14) . . ?
C5 O5 C13 118.20(14) . . ?
C24 O6 C17 111.70(13) . . ?
C25 O9 H9 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.7(3) . . . . ?
O1 C1 C2 C3 176.83(15) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C2 C3 C4 C17 178.56(15) . . . . ?
C3 C4 C5 O5 -178.98(15) . . . . ?
C17 C4 C5 O5 2.4(2) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?
C17 C4 C5 C6 -177.72(15) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
O1 C1 C6 C5 -176.05(14) . . . . ?
O5 C5 C6 C1 179.46(14) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C14 C9 C10 C11 0.4(3) . . . . ?
O3 C9 C10 C11 176.17(16) . . . . ?
C9 C10 C11 C12 -1.5(3) . . . . ?
C10 C11 C12 C13 1.3(3) . . . . ?
C10 C11 C12 C17 -175.89(16) . . . . ?
C11 C12 C13 O5 -179.40(15) . . . . ?
C17 C12 C13 O5 -2.2(2) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C17 C12 C13 C14 177.28(15) . . . . ?
C10 C9 C14 C13 0.9(3) . . . . ?
O3 C9 C14 C13 -175.18(14) . . . . ?
O5 C13 C14 C9 178.35(15) . . . . ?
C12 C13 C14 C9 -1.2(3) . . . . ?
C13 C12 C17 O6 127.63(16) . . . . ?
C11 C12 C17 O6 -55.3(2) . . . . ?
C13 C12 C17 C4 7.6(2) . . . . ?
C11 C12 C17 C4 -175.31(15) . . . . ?
C13 C12 C17 C18 -119.93(17) . . . . ?
C11 C12 C17 C18 57.2(2) . . . . ?
C5 C4 C17 O6 -127.95(16) . . . . ?
C3 C4 C17 O6 53.5(2) . . . . ?
C5 C4 C17 C12 -7.7(2) . . . . ?
C3 C4 C17 C12 173.73(15) . . . . ?
C5 C4 C17 C18 119.94(17) . . . . ?
C3 C4 C17 C18 -58.6(2) . . . . ?
O6 C17 C18 C23 -1.61(18) . . . . ?
C12 C17 C18 C23 -118.37(16) . . . . ?
C4 C17 C18 C23 114.60(16) . . . . ?
O6 C17 C18 C19 178.12(17) . . . . ?
C12 C17 C18 C19 61.4(2) . . . . ?
C4 C17 C18 C19 -65.7(2) . . . . ?
C23 C18 C19 C20 -0.2(3) . . . . ?
C17 C18 C19 C20 -179.88(16) . . . . ?
C18 C19 C20 C21 -1.3(3) . . . . ?
C18 C19 C20 C25 177.43(15) . . . . ?
C19 C20 C21 C22 1.4(3) . . . . ?
C25 C20 C21 C22 -177.21(17) . . . . ?
C20 C21 C22 C23 -0.1(3) . . . . ?
C19 C18 C23 C22 1.5(3) . . . . ?
C17 C18 C23 C22 -178.72(16) . . . . ?
C19 C18 C23 C24 -178.45(15) . . . . ?
C17 C18 C23 C24 1.31(19) . . . . ?
C21 C22 C23 C18 -1.4(3) . . . . ?
C21 C22 C23 C24 178.62(17) . . . . ?
C18 C23 C24 O7 179.33(18) . . . . ?
C22 C23 C24 O7 -0.6(3) . . . . ?
C18 C23 C24 O6 -0.43(19) . . . . ?
C22 C23 C24 O6 179.60(17) . . . . ?
C19 C20 C25 O8 11.2(3) . . . . ?
C21 C20 C25 O8 -170.08(18) . . . . ?
C19 C20 C25 O9 -167.38(15) . . . . ?
C21 C20 C25 O9 11.3(2) . . . . ?
O2 C7 O1 C1 -2.3(3) . . . . ?
C8 C7 O1 C1 176.89(16) . . . . ?
C6 C1 O1 C7 -91.2(2) . . . . ?
C2 C1 O1 C7 93.5(2) . . . . ?
O4 C15 O3 C9 -5.0(3) . . . . ?
C16 C15 O3 C9 173.92(15) . . . . ?
C14 C9 O3 C15 -139.06(17) . . . . ?
C10 C9 O3 C15 44.9(2) . . . . ?
C6 C5 O5 C13 -176.07(14) . . . . ?
C4 C5 O5 C13 3.8(2) . . . . ?
C12 C13 O5 C5 -3.9(2) . . . . ?
C14 C13 O5 C5 176.54(14) . . . . ?
O7 C24 O6 C17 179.57(16) . . . . ?
C23 C24 O6 C17 -0.65(18) . . . . ?
C12 C17 O6 C24 120.65(15) . . . . ?
C4 C17 O6 C24 -117.59(15) . . . . ?
C18 C17 O6 C24 1.35(17) . . . . ?


####################################################################### 
# 
# 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_AcetCl5
_database_code_depnum_ccdc_archive 'CCDC 1498069'
_audit_update_record             
;
2016-08-08 deposited with the CCDC.
2016-09-09 downloaded from the CCDC.
;

_audit_creation_date             2013-04-22T11:52:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 5-carboxy-2',7'-dichlorofluorescein diacetate 2.125-hydrate
;
_chemical_formula_moiety         'C25 H14 Cl2 O9, 1.5(H2 O), O0.625'
_chemical_formula_sum            'C25 H17 Cl2 O11.125'
_chemical_formula_analytical     ?
_chemical_formula_weight         566.29

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.537(12)
_cell_length_b                   13.403(5)
_cell_length_c                   30.553(13)
_cell_angle_alpha                90
_cell_angle_beta                 115.357(6)
_cell_angle_gamma                90
_cell_volume                     10190(7)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    13561
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      33.1
_cell_measurement_temperature    120(2)
_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_absorpt_process_details   'Higashi, 1995'
_exptl_crystal_F_000             4640
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_T_max  0.963

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
        Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            30032
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       36

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total             8968
_reflns_number_gt                7601
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1683
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_refine_ls_number_reflns         8968
_refine_ls_number_parameters     722
_refine_ls_number_restraints     6
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0725P)²+17.8761P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.06
_refine_ls_extinction_method     none
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_cell_refinement       
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction        
;
        CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.86692(14) 0.3175(2) 0.33163(12) 0.0444(8) Uani d . 1 . . C
C2 0.86902(13) 0.3944(3) 0.30154(12) 0.0437(8) Uani d . 1 . . C
C3 0.90968(13) 0.4650(2) 0.31994(12) 0.0398(7) Uani d . 1 . . C
H3 0.9114 0.516 0.3 0.048 Uiso calc R 1 . . H
C4 0.94827(12) 0.4603(2) 0.36834(11) 0.0357(7) Uani d . 1 . . C
C5 0.94449(13) 0.3844(2) 0.39786(11) 0.0369(7) Uani d . 1 . . C
C6 0.90348(14) 0.3136(2) 0.37963(12) 0.0444(8) Uani d . 1 . . C
H6 0.9008 0.2639 0.3998 0.053 Uiso calc R 1 . . H
C7 0.77956(17) 0.2546(3) 0.30282(14) 0.0589(10) Uani d . 1 . . C
C8 0.74537(19) 0.1647(4) 0.27863(17) 0.0797(14) Uani d . 1 . . C
H8A 0.7681 0.1076 0.2834 0.12 Uiso calc R 1 . . H
H8B 0.7257 0.1774 0.2446 0.12 Uiso calc R 1 . . H
H8C 0.7207 0.1522 0.2926 0.12 Uiso calc R 1 . . H
C9 1.10636(14) 0.4670(2) 0.53417(11) 0.0408(7) Uani d . 1 . . C
C10 1.11534(14) 0.5478(2) 0.50972(12) 0.0431(8) Uani d . 1 . . C
C11 1.07909(13) 0.5687(2) 0.46279(12) 0.0417(7) Uani d . 1 . . C
H11 1.0858 0.6218 0.4465 0.05 Uiso calc R 1 . . H
C12 1.03254(13) 0.5116(2) 0.43914(11) 0.0355(7) Uani d . 1 . . C
C13 1.02437(13) 0.4318(2) 0.46475(11) 0.0361(7) Uani d . 1 . . C
C14 1.06108(14) 0.4097(2) 0.51196(11) 0.0398(7) Uani d . 1 . . C
H14 1.0549 0.3563 0.5284 0.048 Uiso calc R 1 . . H
C15 1.18951(16) 0.4054(3) 0.59247(14) 0.0510(9) Uani d . 1 . . C
C16 1.22228(18) 0.3960(3) 0.64614(14) 0.0687(12) Uani d . 1 . . C
H16A 1.2069 0.3455 0.6587 0.103 Uiso calc R 1 . . H
H16B 1.2224 0.4586 0.6614 0.103 Uiso calc R 1 . . H
H16C 1.2585 0.3778 0.6527 0.103 Uiso calc R 1 . . H
C17 0.99221(12) 0.5375(2) 0.38828(11) 0.0342(6) Uani d . 1 . . C
C18 1.01834(12) 0.5645(2) 0.35476(11) 0.0349(6) Uani d . 1 . . C
C19 1.01088(12) 0.6661(2) 0.34386(11) 0.0343(6) Uani d . 1 . . C
C20 1.03366(13) 0.7139(2) 0.31656(10) 0.0351(7) Uani d . 1 . . C
H20 1.0289 0.7819 0.3101 0.042 Uiso calc R 1 . . H
C21 1.06386(13) 0.6555(2) 0.29935(11) 0.0380(7) Uani d . 1 . . C
C22 1.06889(14) 0.5523(2) 0.30811(12) 0.0416(7) Uani d . 1 . . C
H22 1.0873 0.5141 0.2948 0.05 Uiso calc R 1 . . H
C23 1.04697(13) 0.5057(2) 0.33630(12) 0.0403(7) Uani d . 1 . . C
H23 1.0513 0.4376 0.3426 0.048 Uiso calc R 1 . . H
C24 0.97668(12) 0.7073(2) 0.36537(10) 0.0342(6) Uani d . 1 . . C
C25 1.09186(14) 0.7022(2) 0.27170(11) 0.0412(7) Uani d . 1 . . C
O1 0.83113(11) 0.23761(19) 0.31222(9) 0.0573(7) Uani d . 1 . . O
O2 0.76403(11) 0.3320(3) 0.31249(11) 0.0691(8) Uani d . 1 . . O
O3 1.14118(10) 0.44811(18) 0.58271(8) 0.0496(6) Uani d . 1 . . O
O4 1.20217(12) 0.3802(2) 0.56094(10) 0.0631(7) Uani d . 1 . . O
O5 0.98007(9) 0.37115(16) 0.44550(8) 0.0399(5) Uani d . 1 . . O
O6 0.96599(9) 0.63436(15) 0.39117(7) 0.0362(5) Uani d . 1 . . O
O7 0.95811(9) 0.79055(15) 0.36221(8) 0.0397(5) Uani d . 1 . . O
O8 1.11570(11) 0.65328(18) 0.25341(9) 0.0535(6) Uani d . 1 . . O
O9 1.08875(10) 0.80026(16) 0.26978(8) 0.0447(5) Uani d . 1 . . O
H9 1.1095 0.8222 0.2593 0.067 Uiso calc R 1 . . H
Cl1 0.82206(4) 0.39965(7) 0.24144(3) 0.0559(3) Uani d . 1 . . Cl
Cl2 1.17321(4) 0.61961(7) 0.53889(4) 0.0612(3) Uani d . 1 . . Cl
C26 0.58340(16) 0.4503(3) 0.04278(12) 0.0464(8) Uani d . 1 . . C
C27 0.59910(16) 0.5248(3) 0.07771(13) 0.0496(8) Uani d . 1 . . C
C28 0.56670(15) 0.5499(2) 0.10034(12) 0.0456(8) Uani d . 1 . . C
H28 0.578 0.5987 0.1243 0.055 Uiso calc R 1 . . H
C29 0.51703(15) 0.5027(2) 0.08757(11) 0.0408(7) Uani d . 1 . . C
C30 0.50270(15) 0.4265(2) 0.05318(11) 0.0424(8) Uani d . 1 . . C
C31 0.53615(16) 0.4002(2) 0.03109(11) 0.0469(8) Uani d . 1 . . C
H31 0.5263 0.3488 0.0085 0.056 Uiso calc R 1 . . H
C32 0.6570(2) 0.3765(4) 0.03385(16) 0.0732(13) Uani d . 1 . . C
C33 0.6825(2) 0.3690(5) -0.00023(17) 0.0896(17) Uani d . 1 . . C
H33A 0.7206 0.3606 0.0178 0.134 Uiso calc R 1 . . H
H33B 0.6755 0.4289 -0.0192 0.134 Uiso calc R 1 . . H
H33C 0.6679 0.3128 -0.0213 0.134 Uiso calc R 1 . . H
C34 0.34602(14) 0.3356(2) 0.07136(12) 0.0464(8) Uani d . 1 . . C
C35 0.35585(14) 0.4072(2) 0.10795(12) 0.0445(8) Uani d . 1 . . C
C36 0.39929(14) 0.4698(2) 0.12047(11) 0.0415(7) Uani d . 1 . . C
H36 0.4056 0.5179 0.1442 0.05 Uiso calc R 1 . . H
C37 0.43430(14) 0.4626(2) 0.09808(11) 0.0397(7) Uani d . 1 . . C
C38 0.42400(14) 0.3901(2) 0.06272(11) 0.0419(8) Uani d . 1 . . C
C39 0.37933(15) 0.3280(2) 0.04886(12) 0.0476(8) Uani d . 1 . . C
H39 0.3722 0.2814 0.0243 0.057 Uiso calc R 1 . . H
C40 0.30722(15) 0.1778(3) 0.07002(13) 0.0501(8) Uani d . 1 . . C
C41 0.25587(18) 0.1236(3) 0.0525(2) 0.0804(14) Uani d . 1 . . C
H41A 0.2468 0.0988 0.0204 0.121 Uiso calc R 1 . . H
H41B 0.2282 0.168 0.0517 0.121 Uiso calc R 1 . . H
H41C 0.2592 0.0688 0.0738 0.121 Uiso calc R 1 . . H
C42 0.47931(14) 0.5370(2) 0.10889(11) 0.0390(7) Uani d . 1 . . C
C43 0.50922(13) 0.5697(2) 0.16147(11) 0.0371(7) Uani d . 1 . . C
C44 0.50283(13) 0.6712(2) 0.16485(11) 0.0353(7) Uani d . 1 . . C
C45 0.53008(12) 0.7229(2) 0.20820(11) 0.0347(6) Uani d . 1 . . C
H45 0.5252 0.7911 0.2103 0.042 Uiso calc R 1 . . H
C46 0.56477(13) 0.6688(2) 0.24820(11) 0.0361(7) Uani d . 1 . . C
C47 0.57067(14) 0.5647(2) 0.24448(11) 0.0400(7) Uani d . 1 . . C
H47 0.5938 0.5294 0.2716 0.048 Uiso calc R 1 . . H
C48 0.54275(14) 0.5144(2) 0.20122(11) 0.0401(7) Uani d . 1 . . C
H48 0.5464 0.4458 0.199 0.048 Uiso calc R 1 . . H
C49 0.46576(13) 0.7093(2) 0.11617(11) 0.0376(7) Uani d . 1 . . C
C50 0.59629(13) 0.7235(2) 0.29458(11) 0.0392(7) Uani d . 1 . . C
O10 0.61289(11) 0.43296(19) 0.01574(9) 0.0549(7) Uani d . 1 . . O
O11 0.67429(19) 0.3427(3) 0.07426(13) 0.1092(15) Uani d . 1 . . O
O12 0.30016(10) 0.27640(19) 0.05691(10) 0.0583(7) Uani d . 1 . . O
O13 0.35091(12) 0.1436(2) 0.09194(14) 0.0815(10) Uani d . 1 . . O
O14 0.45553(10) 0.37483(16) 0.03832(8) 0.0464(6) Uani d . 1 . . O
O15 0.45364(10) 0.63241(15) 0.08417(7) 0.0414(5) Uani d . 1 . . O
O16 0.44834(10) 0.79281(16) 0.10359(8) 0.0433(5) Uani d . 1 . . O
O17 0.63111(11) 0.66765(18) 0.32877(9) 0.0566(7) Uani d . 1 . . O
H17 0.6502 0.7029 0.3516 0.085 Uiso calc R 1 . . H
O18 0.58943(10) 0.81228(17) 0.29916(8) 0.0497(6) Uani d . 1 . . O
Cl3 0.31226(4) 0.41586(8) 0.13533(3) 0.0552(2) Uani d . 1 . . Cl
Cl4 0.65876(5) 0.58820(8) 0.09160(4) 0.0666(3) Uani d . 1 . . Cl
O19 0.84826(12) 0.8125(2) 0.34247(11) 0.0687(8) Uani d . 1 . . O
H19B 0.8383 0.8385 0.3649 0.103 Uiso d R 1 . . H
H19A 0.8843 0.7985 0.3579 0.103 Uiso d R 1 . . H
O20 0.84291(11) 0.8881(2) 0.25696(10) 0.0555(6) Uani d D 1 . . O
H20A 0.8407(18) 0.860(3) 0.2840(11) 0.083 Uiso d D 1 . . H
H20B 0.8090(10) 0.871(4) 0.2370(13) 0.083 Uiso d D 1 . . H
O21 0.69951(15) 0.7487(3) 0.40647(13) 0.0957(12) Uani d D 1 . . O
H21A 0.699(3) 0.800(4) 0.426(2) 0.144 Uiso d D 1 . . H
H21B 0.7335(14) 0.728(5) 0.426(2) 0.144 Uiso d D 1 . . H
O22A 0.6628(6) 0.8699(15) 0.4554(2) 0.121(6) Uani d P 0.77(3) A 1 O
O22B 0.6879(13) 0.9182(14) 0.4597(10) 0.065(8) Uani d P 0.23(3) A 2 O
O23 0.6728(7) 0.9187(12) 0.3759(5) 0.109(6) Uani d P 0.25 B 2 O



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.379(5) ?
C1 C2 . 1.399(5) ?
C1 O1 . 1.403(4) ?
C2 C3 . 1.388(5) ?
C2 Cl1 . 1.736(3) ?
C3 C4 . 1.405(4) ?
C3 H3 . 0.93 ?
C4 C5 . 1.393(4) ?
C4 C17 . 1.508(4) ?
C5 O5 . 1.374(4) ?
C5 C6 . 1.396(5) ?
C6 H6 . 0.93 ?
C7 O2 . 1.205(5) ?
C7 O1 . 1.343(5) ?
C7 C8 . 1.513(6) ?
C8 H8A . 0.96 ?
C8 H8B . 0.96 ?
C8 H8C . 0.96 ?
C9 C14 . 1.372(5) ?
C9 C10 . 1.396(5) ?
C9 O3 . 1.402(4) ?
C10 C11 . 1.380(5) ?
C10 Cl2 . 1.745(3) ?
C11 C12 . 1.399(5) ?
C11 H11 . 0.93 ?
C12 C13 . 1.399(4) ?
C12 C17 . 1.514(4) ?
C13 O5 . 1.371(4) ?
C13 C14 . 1.393(4) ?
C14 H14 . 0.93 ?
C15 O4 . 1.205(5) ?
C15 O3 . 1.359(5) ?
C15 C16 . 1.500(5) ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 O6 . 1.506(3) ?
C17 C18 . 1.526(4) ?
C18 C23 . 1.394(4) ?
C18 C19 . 1.395(4) ?
C19 C20 . 1.396(4) ?
C19 C24 . 1.468(4) ?
C20 C21 . 1.399(4) ?
C20 H20 . 0.93 ?
C21 C22 . 1.403(4) ?
C21 C25 . 1.502(4) ?
C22 C23 . 1.393(5) ?
C22 H22 . 0.93 ?
C23 H23 . 0.93 ?
C24 O7 . 1.213(4) ?
C24 O6 . 1.365(4) ?
C25 O8 . 1.219(4) ?
C25 O9 . 1.317(4) ?
O9 H9 . 0.82 ?
C26 C31 . 1.369(5) ?
C26 C27 . 1.389(5) ?
C26 O10 . 1.404(4) ?
C27 C28 . 1.384(5) ?
C27 Cl4 . 1.733(4) ?
C28 C29 . 1.402(5) ?
C28 H28 . 0.93 ?
C29 C30 . 1.396(4) ?
C29 C42 . 1.515(5) ?
C30 O14 . 1.367(4) ?
C30 C31 . 1.400(5) ?
C31 H31 . 0.93 ?
C32 O11 . 1.205(5) ?
C32 O10 . 1.334(5) ?
C32 C33 . 1.489(6) ?
C33 H33A . 0.96 ?
C33 H33B . 0.96 ?
C33 H33C . 0.96 ?
C34 C39 . 1.365(5) ?
C34 O12 . 1.394(4) ?
C34 C35 . 1.409(5) ?
C35 C36 . 1.375(5) ?
C35 Cl3 . 1.736(4) ?
C36 C37 . 1.404(5) ?
C36 H36 . 0.93 ?
C37 C38 . 1.389(4) ?
C37 C42 . 1.513(5) ?
C38 O14 . 1.381(4) ?
C38 C39 . 1.393(5) ?
C39 H39 . 0.93 ?
C40 O13 . 1.190(5) ?
C40 O12 . 1.370(4) ?
C40 C41 . 1.471(6) ?
C41 H41A . 0.96 ?
C41 H41B . 0.96 ?
C41 H41C . 0.96 ?
C42 O15 . 1.500(4) ?
C42 C43 . 1.523(4) ?
C43 C44 . 1.381(4) ?
C43 C48 . 1.385(4) ?
C44 C45 . 1.395(4) ?
C44 C49 . 1.488(4) ?
C45 C46 . 1.390(4) ?
C45 H45 . 0.93 ?
C46 C47 . 1.414(4) ?
C46 C50 . 1.498(4) ?
C47 C48 . 1.387(4) ?
C47 H47 . 0.93 ?
C48 H48 . 0.93 ?
C49 O16 . 1.213(4) ?
C49 O15 . 1.360(4) ?
C50 O18 . 1.223(4) ?
C50 O17 . 1.309(4) ?
O17 H17 . 0.82 ?
O19 H19B . 0.908 ?
O19 H19A . 0.9169 ?
O20 H20A . 0.935(19) ?
O20 H20B . 0.900(19) ?
O21 H21A . 0.92(2) ?
O21 H21B . 0.91(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
C6 C1 C2 120.7(3) . . ?
C6 C1 O1 118.7(3) . . ?
C2 C1 O1 120.3(3) . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 Cl1 120.5(3) . . ?
C1 C2 Cl1 120.2(3) . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 C17 120.6(3) . . ?
C3 C4 C17 120.6(3) . . ?
O5 C5 C4 124.3(3) . . ?
O5 C5 C6 115.0(3) . . ?
C4 C5 C6 120.7(3) . . ?
C1 C6 C5 119.7(3) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
O2 C7 O1 123.2(4) . . ?
O2 C7 C8 126.4(4) . . ?
O1 C7 C8 110.4(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 120.1(3) . . ?
C14 C9 O3 119.1(3) . . ?
C10 C9 O3 120.6(3) . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 Cl2 121.0(3) . . ?
C9 C10 Cl2 119.1(3) . . ?
C10 C11 C12 121.4(3) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 117.4(3) . . ?
C13 C12 C17 121.8(3) . . ?
C11 C12 C17 120.8(3) . . ?
O5 C13 C14 115.8(3) . . ?
O5 C13 C12 122.7(3) . . ?
C14 C13 C12 121.5(3) . . ?
C9 C14 C13 119.7(3) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
O4 C15 O3 122.3(3) . . ?
O4 C15 C16 127.3(4) . . ?
O3 C15 C16 110.5(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O6 C17 C4 107.0(2) . . ?
O6 C17 C12 107.3(2) . . ?
C4 C17 C12 111.5(2) . . ?
O6 C17 C18 102.1(2) . . ?
C4 C17 C18 114.8(2) . . ?
C12 C17 C18 113.2(3) . . ?
C23 C18 C19 120.4(3) . . ?
C23 C18 C17 130.4(3) . . ?
C19 C18 C17 109.2(3) . . ?
C18 C19 C20 122.2(3) . . ?
C18 C19 C24 108.5(3) . . ?
C20 C19 C24 129.3(3) . . ?
C19 C20 C21 117.4(3) . . ?
C19 C20 H20 121.3 . . ?
C21 C20 H20 121.3 . . ?
C20 C21 C22 120.4(3) . . ?
C20 C21 C25 120.6(3) . . ?
C22 C21 C25 119.0(3) . . ?
C23 C22 C21 121.7(3) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C22 C23 C18 117.8(3) . . ?
C22 C23 H23 121.1 . . ?
C18 C23 H23 121.1 . . ?
O7 C24 O6 121.1(3) . . ?
O7 C24 C19 129.8(3) . . ?
O6 C24 C19 109.1(2) . . ?
O8 C25 O9 123.6(3) . . ?
O8 C25 C21 122.7(3) . . ?
O9 C25 C21 113.7(3) . . ?
C7 O1 C1 116.6(3) . . ?
C15 O3 C9 118.0(3) . . ?
C13 O5 C5 118.5(2) . . ?
C24 O6 C17 110.9(2) . . ?
C25 O9 H9 109.5 . . ?
C31 C26 C27 120.1(3) . . ?
C31 C26 O10 119.3(3) . . ?
C27 C26 O10 120.2(3) . . ?
C28 C27 C26 120.2(4) . . ?
C28 C27 Cl4 120.3(3) . . ?
C26 C27 Cl4 119.4(3) . . ?
C27 C28 C29 120.8(3) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C30 C29 C28 117.9(3) . . ?
C30 C29 C42 121.4(3) . . ?
C28 C29 C42 120.7(3) . . ?
O14 C30 C29 122.9(3) . . ?
O14 C30 C31 116.1(3) . . ?
C29 C30 C31 121.0(3) . . ?
C26 C31 C30 119.9(3) . . ?
C26 C31 H31 120 . . ?
C30 C31 H31 120 . . ?
O11 C32 O10 121.9(4) . . ?
O11 C32 C33 126.4(4) . . ?
O10 C32 C33 111.5(4) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C39 C34 O12 120.7(3) . . ?
C39 C34 C35 120.6(3) . . ?
O12 C34 C35 118.6(3) . . ?
C36 C35 C34 119.0(3) . . ?
C36 C35 Cl3 121.6(3) . . ?
C34 C35 Cl3 119.4(3) . . ?
C35 C36 C37 121.3(3) . . ?
C35 C36 H36 119.4 . . ?
C37 C36 H36 119.4 . . ?
C38 C37 C36 118.2(3) . . ?
C38 C37 C42 120.4(3) . . ?
C36 C37 C42 121.2(3) . . ?
O14 C38 C37 123.9(3) . . ?
O14 C38 C39 115.1(3) . . ?
C37 C38 C39 121.0(3) . . ?
C34 C39 C38 119.9(3) . . ?
C34 C39 H39 120.1 . . ?
C38 C39 H39 120.1 . . ?
O13 C40 O12 121.3(4) . . ?
O13 C40 C41 126.7(4) . . ?
O12 C40 C41 112.0(3) . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
O15 C42 C37 106.7(3) . . ?
O15 C42 C29 107.7(2) . . ?
C37 C42 C29 110.8(3) . . ?
O15 C42 C43 102.2(2) . . ?
C37 C42 C43 116.3(3) . . ?
C29 C42 C43 112.4(3) . . ?
C44 C43 C48 121.4(3) . . ?
C44 C43 C42 109.5(3) . . ?
C48 C43 C42 128.9(3) . . ?
C43 C44 C45 121.7(3) . . ?
C43 C44 C49 108.6(3) . . ?
C45 C44 C49 129.7(3) . . ?
C46 C45 C44 117.6(3) . . ?
C46 C45 H45 121.2 . . ?
C44 C45 H45 121.2 . . ?
C45 C46 C47 120.2(3) . . ?
C45 C46 C50 118.6(3) . . ?
C47 C46 C50 121.2(3) . . ?
C48 C47 C46 121.4(3) . . ?
C48 C47 H47 119.3 . . ?
C46 C47 H47 119.3 . . ?
C43 C48 C47 117.7(3) . . ?
C43 C48 H48 121.2 . . ?
C47 C48 H48 121.2 . . ?
O16 C49 O15 122.0(3) . . ?
O16 C49 C44 129.9(3) . . ?
O15 C49 C44 108.1(2) . . ?
O18 C50 O17 124.2(3) . . ?
O18 C50 C46 121.9(3) . . ?
O17 C50 C46 113.9(3) . . ?
C32 O10 C26 120.2(3) . . ?
C40 O12 C34 117.4(3) . . ?
C30 O14 C38 118.3(2) . . ?
C49 O15 C42 111.5(2) . . ?
C50 O17 H17 109.5 . . ?
H19B O19 H19A 107.3 . . ?
H20A O20 H20B 93(3) . . ?
H21A O21 H21B 94(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 2.5(5) . . . . ?
O1 C1 C2 C3 -170.8(3) . . . . ?
C6 C1 C2 Cl1 -179.0(3) . . . . ?
O1 C1 C2 Cl1 7.7(5) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
Cl1 C2 C3 C4 -179.0(2) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C2 C3 C4 C17 -179.6(3) . . . . ?
C3 C4 C5 O5 179.1(3) . . . . ?
C17 C4 C5 O5 -2.3(5) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C17 C4 C5 C6 179.2(3) . . . . ?
C2 C1 C6 C5 -2.9(5) . . . . ?
O1 C1 C6 C5 170.5(3) . . . . ?
O5 C5 C6 C1 -177.3(3) . . . . ?
C4 C5 C6 C1 1.3(5) . . . . ?
C14 C9 C10 C11 -1.3(5) . . . . ?
O3 C9 C10 C11 -176.5(3) . . . . ?
C14 C9 C10 Cl2 179.9(3) . . . . ?
O3 C9 C10 Cl2 4.7(4) . . . . ?
C9 C10 C11 C12 1.3(5) . . . . ?
Cl2 C10 C11 C12 -179.9(3) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
C10 C11 C12 C17 177.9(3) . . . . ?
C11 C12 C13 O5 179.5(3) . . . . ?
C17 C12 C13 O5 1.0(5) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C17 C12 C13 C14 -178.6(3) . . . . ?
C10 C9 C14 C13 0.6(5) . . . . ?
O3 C9 C14 C13 175.9(3) . . . . ?
O5 C13 C14 C9 -179.5(3) . . . . ?
C12 C13 C14 C9 0.0(5) . . . . ?
C5 C4 C17 O6 -109.3(3) . . . . ?
C3 C4 C17 O6 69.2(3) . . . . ?
C5 C4 C17 C12 7.8(4) . . . . ?
C3 C4 C17 C12 -173.7(3) . . . . ?
C5 C4 C17 C18 138.2(3) . . . . ?
C3 C4 C17 C18 -43.3(4) . . . . ?
C13 C12 C17 O6 109.7(3) . . . . ?
C11 C12 C17 O6 -68.7(4) . . . . ?
C13 C12 C17 C4 -7.2(4) . . . . ?
C11 C12 C17 C4 174.4(3) . . . . ?
C13 C12 C17 C18 -138.4(3) . . . . ?
C11 C12 C17 C18 43.2(4) . . . . ?
O6 C17 C18 C23 -177.1(3) . . . . ?
C4 C17 C18 C23 -61.7(4) . . . . ?
C12 C17 C18 C23 67.9(4) . . . . ?
O6 C17 C18 C19 4.2(3) . . . . ?
C4 C17 C18 C19 119.7(3) . . . . ?
C12 C17 C18 C19 -110.8(3) . . . . ?
C23 C18 C19 C20 -3.4(5) . . . . ?
C17 C18 C19 C20 175.5(3) . . . . ?
C23 C18 C19 C24 176.4(3) . . . . ?
C17 C18 C19 C24 -4.8(3) . . . . ?
C18 C19 C20 C21 1.2(4) . . . . ?
C24 C19 C20 C21 -178.5(3) . . . . ?
C19 C20 C21 C22 2.3(5) . . . . ?
C19 C20 C21 C25 -177.1(3) . . . . ?
C20 C21 C22 C23 -3.8(5) . . . . ?
C25 C21 C22 C23 175.6(3) . . . . ?
C21 C22 C23 C18 1.7(5) . . . . ?
C19 C18 C23 C22 1.8(5) . . . . ?
C17 C18 C23 C22 -176.7(3) . . . . ?
C18 C19 C24 O7 -175.3(3) . . . . ?
C20 C19 C24 O7 4.4(6) . . . . ?
C18 C19 C24 O6 3.4(3) . . . . ?
C20 C19 C24 O6 -176.9(3) . . . . ?
C20 C21 C25 O8 -175.2(3) . . . . ?
C22 C21 C25 O8 5.5(5) . . . . ?
C20 C21 C25 O9 5.7(4) . . . . ?
C22 C21 C25 O9 -173.7(3) . . . . ?
O2 C7 O1 C1 -3.8(6) . . . . ?
C8 C7 O1 C1 175.7(3) . . . . ?
C6 C1 O1 C7 108.0(4) . . . . ?
C2 C1 O1 C7 -78.5(4) . . . . ?
O4 C15 O3 C9 -3.0(5) . . . . ?
C16 C15 O3 C9 177.0(3) . . . . ?
C14 C9 O3 C15 108.2(4) . . . . ?
C10 C9 O3 C15 -76.6(4) . . . . ?
C14 C13 O5 C5 -175.1(3) . . . . ?
C12 C13 O5 C5 5.4(4) . . . . ?
C4 C5 O5 C13 -4.7(4) . . . . ?
C6 C5 O5 C13 173.8(3) . . . . ?
O7 C24 O6 C17 178.3(3) . . . . ?
C19 C24 O6 C17 -0.6(3) . . . . ?
C4 C17 O6 C24 -123.1(3) . . . . ?
C12 C17 O6 C24 117.1(3) . . . . ?
C18 C17 O6 C24 -2.2(3) . . . . ?
C31 C26 C27 C28 -1.0(5) . . . . ?
O10 C26 C27 C28 172.4(3) . . . . ?
C31 C26 C27 Cl4 -179.4(3) . . . . ?
O10 C26 C27 Cl4 -6.0(5) . . . . ?
C26 C27 C28 C29 -1.7(5) . . . . ?
Cl4 C27 C28 C29 176.7(3) . . . . ?
C27 C28 C29 C30 3.1(5) . . . . ?
C27 C28 C29 C42 -174.1(3) . . . . ?
C28 C29 C30 O14 179.4(3) . . . . ?
C42 C29 C30 O14 -3.3(5) . . . . ?
C28 C29 C30 C31 -1.9(5) . . . . ?
C42 C29 C30 C31 175.3(3) . . . . ?
C27 C26 C31 C30 2.2(5) . . . . ?
O10 C26 C31 C30 -171.2(3) . . . . ?
O14 C30 C31 C26 178.0(3) . . . . ?
C29 C30 C31 C26 -0.7(5) . . . . ?
C39 C34 C35 C36 0.5(5) . . . . ?
O12 C34 C35 C36 -176.3(3) . . . . ?
C39 C34 C35 Cl3 179.2(3) . . . . ?
O12 C34 C35 Cl3 2.5(4) . . . . ?
C34 C35 C36 C37 -1.0(5) . . . . ?
Cl3 C35 C36 C37 -179.8(2) . . . . ?
C35 C36 C37 C38 0.0(5) . . . . ?
C35 C36 C37 C42 174.8(3) . . . . ?
C36 C37 C38 O14 -179.4(3) . . . . ?
C42 C37 C38 O14 5.7(5) . . . . ?
C36 C37 C38 C39 1.7(5) . . . . ?
C42 C37 C38 C39 -173.2(3) . . . . ?
O12 C34 C39 C38 177.8(3) . . . . ?
C35 C34 C39 C38 1.2(5) . . . . ?
O14 C38 C39 C34 178.8(3) . . . . ?
C37 C38 C39 C34 -2.3(5) . . . . ?
C38 C37 C42 O15 101.5(3) . . . . ?
C36 C37 C42 O15 -73.3(3) . . . . ?
C38 C37 C42 C29 -15.5(4) . . . . ?
C36 C37 C42 C29 169.7(3) . . . . ?
C38 C37 C42 C43 -145.4(3) . . . . ?
C36 C37 C42 C43 39.9(4) . . . . ?
C30 C29 C42 O15 -101.8(3) . . . . ?
C28 C29 C42 O15 75.4(3) . . . . ?
C30 C29 C42 C37 14.5(4) . . . . ?
C28 C29 C42 C37 -168.3(3) . . . . ?
C30 C29 C42 C43 146.4(3) . . . . ?
C28 C29 C42 C43 -36.4(4) . . . . ?
O15 C42 C43 C44 -2.4(3) . . . . ?
C37 C42 C43 C44 -118.2(3) . . . . ?
C29 C42 C43 C44 112.7(3) . . . . ?
O15 C42 C43 C48 -176.4(3) . . . . ?
C37 C42 C43 C48 67.9(5) . . . . ?
C29 C42 C43 C48 -61.2(4) . . . . ?
C48 C43 C44 C45 0.6(5) . . . . ?
C42 C43 C44 C45 -173.9(3) . . . . ?
C48 C43 C44 C49 178.5(3) . . . . ?
C42 C43 C44 C49 4.0(4) . . . . ?
C43 C44 C45 C46 0.8(5) . . . . ?
C49 C44 C45 C46 -176.7(3) . . . . ?
C44 C45 C46 C47 -1.3(4) . . . . ?
C44 C45 C46 C50 177.4(3) . . . . ?
C45 C46 C47 C48 0.6(5) . . . . ?
C50 C46 C47 C48 -178.1(3) . . . . ?
C44 C43 C48 C47 -1.3(5) . . . . ?
C42 C43 C48 C47 172.0(3) . . . . ?
C46 C47 C48 C43 0.7(5) . . . . ?
C43 C44 C49 O16 177.6(3) . . . . ?
C45 C44 C49 O16 -4.7(6) . . . . ?
C43 C44 C49 O15 -4.1(4) . . . . ?
C45 C44 C49 O15 173.6(3) . . . . ?
C45 C46 C50 O18 5.5(5) . . . . ?
C47 C46 C50 O18 -175.8(3) . . . . ?
C45 C46 C50 O17 -174.4(3) . . . . ?
C47 C46 C50 O17 4.3(4) . . . . ?
O11 C32 O10 C26 -3.6(7) . . . . ?
C33 C32 O10 C26 -179.1(4) . . . . ?
C31 C26 O10 C32 -103.7(4) . . . . ?
C27 C26 O10 C32 82.9(5) . . . . ?
O13 C40 O12 C34 -1.7(6) . . . . ?
C41 C40 O12 C34 -179.8(4) . . . . ?
C39 C34 O12 C40 74.6(4) . . . . ?
C35 C34 O12 C40 -108.6(4) . . . . ?
C29 C30 O14 C38 -8.3(4) . . . . ?
C31 C30 O14 C38 172.9(3) . . . . ?
C37 C38 O14 C30 7.2(4) . . . . ?
C39 C38 O14 C30 -173.9(3) . . . . ?
O16 C49 O15 C42 -179.0(3) . . . . ?
C44 C49 O15 C42 2.5(3) . . . . ?
C37 C42 O15 C49 122.4(3) . . . . ?
C29 C42 O15 C49 -118.7(3) . . . . ?
C43 C42 O15 C49 -0.1(3) . . . . ?

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 H9 O20 0.82 1.82 2.629(3) 170.4 2_755
O17 H17 O21 0.82 1.76 2.556(4) 165 .
O19 H19A O7 0.92 1.98 2.835(4) 153.7 .
O19 H19B O11 0.91 2.03 2.894(5) 157.5 4_655
O20 H20A O19 0.935(19) 1.82(2) 2.746(4) 170(4) .
O20 H20B O2 0.900(19) 2.00(2) 2.896(4) 175(4) 4_655
O21 H21B O4 0.91(2) 2.20(4) 3.000(5) 146(6) 5_766
O21 H21A O22A 0.92(2) 1.85(4) 2.681(7) 149(6) .
O21 H21A O22B 0.92(2) 1.98(3) 2.89(2) 170(6) .

