# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_X-TTF-1_oDCB
_database_code_depnum_ccdc_archive 'CCDC 1499634'
_audit_update_record             
;
2017-02-07 deposited with the CCDC.
2017-02-09 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C58 H36 Cl8 O8 S4'
_chemical_formula_moiety         'C34 H20 O8 S4, 4(C6 H4 Cl2)'
_chemical_formula_weight         1272.71
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   10.0210(3)
_cell_length_b                   16.1986(5)
_cell_length_c                   18.3286(5)
_cell_angle_alpha                76.430(3)
_cell_angle_beta                 87.497(2)
_cell_angle_gamma                74.082(3)
_cell_volume                     2780.58(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11482
_cell_measurement_theta_min      1.74
_cell_measurement_theta_max      32.23
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       columnar
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             898.00
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.80000
_diffrn_measurement_device_type  'SPring-8, BL38B1, CCD(MX225HE Rayonix)'
_diffrn_reflns_number            17343
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_theta_max         28.700
_diffrn_reflns_theta_min         1.744
_diffrn_reflns_theta_full        28.685
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measured_fraction_theta_full 0.899
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_Laue_measured_fraction_full 0.899
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_point_group_measured_fraction_full 0.899
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             9053
_reflns_number_gt                8137
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1724
_refine_ls_wR_factor_gt          0.1623
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         9053
_refine_ls_number_parameters     707
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1174P)²+3.9235P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.09
_refine_diff_density_min         -0.68
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.33839(12) 0.24213(7) 0.19654(5) 0.0431(3) Uani 1 1 d . . . . .
Cl2 Cl -0.33047(12) 0.17079(7) 0.37299(6) 0.0462(3) Uani 1 1 d . . . . .
Cl3 Cl -0.01955(11) 0.03686(7) 0.25934(6) 0.0462(3) Uani 1 1 d . . . . .
Cl4 Cl 0.09546(13) 0.01271(7) 0.42306(6) 0.0503(3) Uani 1 1 d . . . . .
Cl5 Cl 0.01631(10) 0.20706(6) 0.56822(5) 0.0364(2) Uani 1 1 d . . . . .
Cl6 Cl 0.18938(10) 0.34214(6) 0.49653(5) 0.0371(2) Uani 1 1 d . . . . .
Cl7 Cl 0.68403(16) 0.14869(11) 0.72424(10) 0.0791(4) Uani 1 1 d . . . . .
Cl8 Cl 0.41390(13) 0.30677(7) 0.68058(6) 0.0517(3) Uani 1 1 d . . . . .
S1 S 0.12478(8) 0.45411(5) -0.09879(4) 0.01720(19) Uani 1 1 d . . . . .
S2 S 0.10509(8) 0.32518(5) 0.04152(4) 0.01755(19) Uani 1 1 d . . . . .
S3 S 0.25534(8) 0.42294(5) 0.13334(4) 0.01735(19) Uani 1 1 d . . . . .
S4 S 0.27128(8) 0.55456(4) -0.00523(4) 0.01717(19) Uani 1 1 d . . . . .
O1 O -0.1235(3) 0.45023(15) -0.45476(11) 0.0252(5) Uani 1 1 d . . . . .
H1 H -0.1626 0.4512 -0.4935 0.030 Uiso 1 1 calc R U . . .
O2 O -0.2694(3) 0.37118(17) -0.40178(12) 0.0298(5) Uani 1 1 d . . . . .
O3 O -0.2058(2) -0.00748(14) -0.07196(12) 0.0244(5) Uani 1 1 d . . . . .
H3 H -0.2574 -0.0399 -0.0662 0.029 Uiso 1 1 calc R U . . .
O4 O -0.3024(2) 0.02320(14) 0.03498(12) 0.0237(5) Uani 1 1 d . . . . .
O5 O 0.5858(3) 0.39198(18) 0.47858(12) 0.0322(6) Uani 1 1 d . . . . .
H5 H 0.6316 0.3869 0.5162 0.039 Uiso 1 1 calc R U . . .
O6 O 0.7425(3) 0.46037(16) 0.42185(12) 0.0280(5) Uani 1 1 d . . . . .
O7 O 0.5855(3) 0.89311(14) 0.06818(12) 0.0255(5) Uani 1 1 d . . . . .
H7 H 0.6137 0.9372 0.0549 0.031 Uiso 1 1 calc R U . . .
O8 O 0.6445(2) 0.87842(14) -0.04866(11) 0.0224(5) Uani 1 1 d . . . . .
C1 C 0.0618(3) 0.36461(19) -0.10638(16) 0.0176(6) Uani 1 1 d . . . . .
C2 C 0.0555(3) 0.30455(19) -0.04177(15) 0.0170(6) Uani 1 1 d . . . . .
C3 C 0.1585(3) 0.41887(18) -0.00144(15) 0.0152(6) Uani 1 1 d . . . . .
C4 C 0.2181(3) 0.46051(19) 0.03653(15) 0.0167(6) Uani 1 1 d . . . . .
C5 C 0.3625(3) 0.49228(18) 0.13688(16) 0.0177(6) Uani 1 1 d . . . . .
C6 C 0.3676(3) 0.55438(18) 0.07307(15) 0.0149(6) Uani 1 1 d . . . . .
C7 C 0.0069(3) 0.37123(19) -0.18146(16) 0.0188(6) Uani 1 1 d . . . . .
C8 C 0.0687(3) 0.4079(2) -0.24644(17) 0.0217(6) Uani 1 1 d . . . . .
H8 H 0.1485 0.4254 -0.2421 0.026 Uiso 1 1 calc R U . . .
C9 C 0.0135(4) 0.4187(2) -0.31707(17) 0.0229(7) Uani 1 1 d . . . . .
H9 H 0.0552 0.4440 -0.3596 0.027 Uiso 1 1 calc R U . . .
C10 C -0.1051(3) 0.39160(19) -0.32428(16) 0.0198(6) Uani 1 1 d . . . . .
C11 C -0.1657(3) 0.3534(2) -0.25998(16) 0.0201(6) Uani 1 1 d . . . . .
H11 H -0.2427 0.3333 -0.2645 0.024 Uiso 1 1 calc R U . . .
C12 C -0.1126(3) 0.34509(19) -0.18965(16) 0.0189(6) Uani 1 1 d . . . . .
H12 H -0.1566 0.3219 -0.1472 0.023 Uiso 1 1 calc R U . . .
C13 C -0.1727(3) 0.4036(2) -0.39756(17) 0.0218(7) Uani 1 1 d . . . . .
C14 C -0.0018(3) 0.22801(18) -0.03225(16) 0.0175(6) Uani 1 1 d . . . . .
C15 C 0.0290(3) 0.17213(19) -0.08230(16) 0.0185(6) Uani 1 1 d . . . . .
H15 H 0.0968 0.1775 -0.1180 0.022 Uiso 1 1 calc R U . . .
C16 C -0.0423(3) 0.10848(19) -0.07853(16) 0.0198(6) Uani 1 1 d . . . . .
H16 H -0.0252 0.0731 -0.1131 0.024 Uiso 1 1 calc R U . . .
C17 C -0.1395(3) 0.09808(19) -0.02256(16) 0.0186(6) Uani 1 1 d . . . . .
C18 C -0.1614(3) 0.14876(19) 0.03091(16) 0.0195(6) Uani 1 1 d . . . . .
H18 H -0.2220 0.1392 0.0699 0.023 Uiso 1 1 calc R U . . .
C19 C -0.0932(3) 0.21315(19) 0.02606(16) 0.0185(6) Uani 1 1 d . . . . .
H19 H -0.1081 0.2469 0.0618 0.022 Uiso 1 1 calc R U . . .
C20 C -0.2236(3) 0.03441(19) -0.01742(16) 0.0189(6) Uani 1 1 d . . . . .
C21 C 0.4346(3) 0.47450(18) 0.20941(16) 0.0181(6) Uani 1 1 d . . . . .
C22 C 0.3718(3) 0.4447(2) 0.27639(16) 0.0203(6) Uani 1 1 d . . . . .
H22 H 0.2849 0.4350 0.2748 0.024 Uiso 1 1 calc R U . . .
C23 C 0.4375(3) 0.4296(2) 0.34495(17) 0.0215(6) Uani 1 1 d . . . . .
H23 H 0.3951 0.4094 0.3891 0.026 Uiso 1 1 calc R U . . .
C24 C 0.5682(3) 0.44483(19) 0.34759(16) 0.0197(6) Uani 1 1 d . . . . .
C25 C 0.6320(3) 0.47214(19) 0.28082(17) 0.0205(6) Uani 1 1 d . . . . .
H25 H 0.7192 0.4815 0.2823 0.025 Uiso 1 1 calc R U . . .
C26 C 0.5676(3) 0.48553(19) 0.21263(16) 0.0194(6) Uani 1 1 d . . . . .
H26 H 0.6127 0.5020 0.1684 0.023 Uiso 1 1 calc R U . . .
C27 C 0.6396(4) 0.4331(2) 0.41964(17) 0.0229(7) Uani 1 1 d . . . . .
C28 C 0.4305(3) 0.62904(18) 0.06027(16) 0.0161(6) Uani 1 1 d . . . . .
C29 C 0.4755(3) 0.66097(19) -0.01173(16) 0.0171(6) Uani 1 1 d . . . . .
H29 H 0.4704 0.6328 -0.0498 0.021 Uiso 1 1 calc R U . . .
C30 C 0.5277(3) 0.73398(19) -0.02683(16) 0.0177(6) Uani 1 1 d . . . . .
H30 H 0.5581 0.7540 -0.0747 0.021 Uiso 1 1 calc R U . . .
C31 C 0.5345(3) 0.77736(19) 0.02942(16) 0.0186(6) Uani 1 1 d . . . . .
C32 C 0.4885(3) 0.7469(2) 0.10133(16) 0.0196(6) Uani 1 1 d . . . . .
H32 H 0.4923 0.7760 0.1390 0.023 Uiso 1 1 calc R U . . .
C33 C 0.4374(3) 0.67372(19) 0.11644(16) 0.0187(6) Uani 1 1 d . . . . .
H33 H 0.4072 0.6538 0.1644 0.022 Uiso 1 1 calc R U . . .
C34 C 0.5932(3) 0.85453(19) 0.01229(17) 0.0197(6) Uani 1 1 d . . . . .
C35 C -0.2221(4) 0.2630(2) 0.25307(19) 0.0291(7) Uani 1 1 d . . . . .
C36 C -0.2199(4) 0.2320(2) 0.33020(19) 0.0310(8) Uani 1 1 d . . . . .
C37 C -0.1275(4) 0.2503(3) 0.3739(2) 0.0376(9) Uani 1 1 d . . . . .
H37 H -0.1246 0.2293 0.4258 0.045 Uiso 1 1 calc R U . . .
C38 C -0.0394(5) 0.2997(3) 0.3404(3) 0.0444(10) Uani 1 1 d . . . . .
H38 H 0.0216 0.3128 0.3700 0.053 Uiso 1 1 calc R U . . .
C39 C -0.0413(4) 0.3298(3) 0.2634(3) 0.0427(10) Uani 1 1 d . . . . .
H39 H 0.0191 0.3625 0.2412 0.051 Uiso 1 1 calc R U . . .
C40 C -0.1327(4) 0.3117(2) 0.2193(2) 0.0356(8) Uani 1 1 d . . . . .
H40 H -0.1343 0.3320 0.1674 0.043 Uiso 1 1 calc R U . . .
C41 C 0.1083(4) 0.0848(2) 0.2744(2) 0.0326(8) Uani 1 1 d . . . . .
C42 C 0.1585(4) 0.0748(2) 0.3462(2) 0.0328(8) Uani 1 1 d . . . . .
C43 C 0.2582(4) 0.1148(2) 0.3577(2) 0.0354(8) Uani 1 1 d . . . . .
H43 H 0.2904 0.1085 0.4060 0.042 Uiso 1 1 calc R U . . .
C44 C 0.3107(4) 0.1649(2) 0.2961(2) 0.0375(9) Uani 1 1 d . . . . .
H44 H 0.3782 0.1920 0.3031 0.045 Uiso 1 1 calc R U . . .
C45 C 0.2610(5) 0.1735(2) 0.2249(2) 0.0396(9) Uani 1 1 d . . . . .
H45 H 0.2959 0.2066 0.1839 0.048 Uiso 1 1 calc R U . . .
C46 C 0.1612(4) 0.1341(2) 0.2135(2) 0.0353(8) Uani 1 1 d . . . . .
H46 H 0.1291 0.1404 0.1651 0.042 Uiso 1 1 calc R U . . .
C47 C 0.2704(4) 0.2303(2) 0.52588(19) 0.0305(8) Uani 1 1 d . . . . .
C48 C 0.4133(4) 0.2004(3) 0.52052(19) 0.0346(8) Uani 1 1 d . . . . .
H48 H 0.4643 0.2403 0.5006 0.042 Uiso 1 1 calc R U . . .
C49 C 0.4799(4) 0.1121(3) 0.5445(2) 0.0369(8) Uani 1 1 d . . . . .
H49 H 0.5757 0.0922 0.5408 0.044 Uiso 1 1 calc R U . . .
C50 C 0.4027(4) 0.0523(3) 0.5745(2) 0.0381(9) Uani 1 1 d . . . . .
H50 H 0.4474 -0.0074 0.5907 0.046 Uiso 1 1 calc R U . . .
C51 C 0.2604(4) 0.0816(2) 0.58011(19) 0.0340(8) Uani 1 1 d . . . . .
H51 H 0.2094 0.0417 0.5997 0.041 Uiso 1 1 calc R U . . .
C52 C 0.1940(4) 0.1707(2) 0.55639(18) 0.0305(8) Uani 1 1 d . . . . .
C53 C 0.5209(5) 0.1309(3) 0.7395(2) 0.0502(11) Uani 1 1 d . . . . .
C54 C 0.4001(5) 0.2008(3) 0.7197(2) 0.0427(10) Uani 1 1 d . . . . .
C55 C 0.2712(6) 0.1861(3) 0.7311(2) 0.0462(11) Uani 1 1 d . . . . .
H55 H 0.1913 0.2324 0.7181 0.055 Uiso 1 1 calc R U . . .
C56 C 0.2622(6) 0.1008(3) 0.7626(2) 0.0599(14) Uani 1 1 d . . . . .
H56 H 0.1755 0.0903 0.7706 0.072 Uiso 1 1 calc R U . . .
C57 C 0.3841(7) 0.0296(3) 0.7828(2) 0.0622(16) Uani 1 1 d . . . . .
H57 H 0.3784 -0.0274 0.8038 0.075 Uiso 1 1 calc R U . . .
C58 C 0.5099(7) 0.0478(3) 0.7704(3) 0.0612(14) Uani 1 1 d . . . . .
H58 H 0.5905 0.0020 0.7833 0.073 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXD Version 2013/2 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C35 1.741(4) . ?
Cl2 C36 1.729(4) . ?
Cl3 C41 1.732(4) . ?
Cl4 C42 1.733(3) . ?
Cl5 C52 1.737(4) . ?
Cl6 C47 1.734(4) . ?
Cl7 C53 1.737(5) . ?
Cl8 C54 1.738(4) . ?
S1 C3 1.759(3) . ?
S1 C1 1.767(3) . ?
S2 C3 1.749(3) . ?
S2 C2 1.757(3) . ?
S3 C4 1.756(3) . ?
S3 C5 1.767(3) . ?
S4 C4 1.747(3) . ?
S4 C6 1.763(3) . ?
O1 C13 1.304(4) . ?
O1 H1 0.8200 . ?
O2 C13 1.235(4) . ?
O3 C20 1.314(4) . ?
O3 H3 0.8200 . ?
O4 C20 1.229(4) . ?
O5 C27 1.307(4) . ?
O5 H5 0.8200 . ?
O6 C27 1.234(4) . ?
O7 C34 1.309(4) . ?
O7 H7 0.8200 . ?
O8 C34 1.232(4) . ?
C1 C2 1.356(4) . ?
C1 C7 1.474(4) . ?
C2 C14 1.475(4) . ?
C3 C4 1.332(4) . ?
C5 C6 1.361(4) . ?
C5 C21 1.471(4) . ?
C6 C28 1.479(4) . ?
C7 C12 1.400(4) . ?
C7 C8 1.400(4) . ?
C8 C9 1.384(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.396(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.394(4) . ?
C10 C13 1.478(4) . ?
C11 C12 1.379(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C14 C19 1.398(4) . ?
C14 C15 1.403(4) . ?
C15 C16 1.394(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.397(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.394(4) . ?
C17 C20 1.485(4) . ?
C18 C19 1.380(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C21 C26 1.397(4) . ?
C21 C22 1.399(4) . ?
C22 C23 1.382(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.403(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.391(4) . ?
C24 C27 1.477(4) . ?
C25 C26 1.375(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C28 C29 1.403(4) . ?
C28 C33 1.404(4) . ?
C29 C30 1.386(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.391(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.400(4) . ?
C31 C34 1.487(4) . ?
C32 C33 1.382(4) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C35 C36 1.384(5) . ?
C35 C40 1.385(5) . ?
C36 C37 1.384(5) . ?
C37 C38 1.381(6) . ?
C37 H37 0.9300 . ?
C38 C39 1.380(6) . ?
C38 H38 0.9300 . ?
C39 C40 1.380(6) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
C41 C42 1.387(5) . ?
C41 C46 1.388(5) . ?
C42 C43 1.378(5) . ?
C43 C44 1.400(5) . ?
C43 H43 0.9300 . ?
C44 C45 1.380(6) . ?
C44 H44 0.9300 . ?
C45 C46 1.371(6) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C47 C48 1.387(5) . ?
C47 C52 1.394(5) . ?
C48 C49 1.375(5) . ?
C48 H48 0.9300 . ?
C49 C50 1.401(5) . ?
C49 H49 0.9300 . ?
C50 C51 1.381(6) . ?
C50 H50 0.9300 . ?
C51 C52 1.385(5) . ?
C51 H51 0.9300 . ?
C53 C58 1.364(7) . ?
C53 C54 1.405(7) . ?
C54 C55 1.375(7) . ?
C55 C56 1.392(6) . ?
C55 H55 0.9300 . ?
C56 C57 1.423(8) . ?
C56 H56 0.9300 . ?
C57 C58 1.370(8) . ?
C57 H57 0.9300 . ?
C58 H58 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S1 C1 95.71(13) . . ?
C3 S2 C2 96.12(13) . . ?
C4 S3 C5 95.74(13) . . ?
C4 S4 C6 96.13(13) . . ?
C13 O1 H1 109.5 . . ?
C20 O3 H3 109.5 . . ?
C27 O5 H5 109.5 . . ?
C34 O7 H7 109.5 . . ?
C2 C1 C7 128.1(2) . . ?
C2 C1 S1 116.7(2) . . ?
C7 C1 S1 114.7(2) . . ?
C1 C2 C14 127.2(3) . . ?
C1 C2 S2 116.9(2) . . ?
C14 C2 S2 115.6(2) . . ?
C4 C3 S2 122.8(2) . . ?
C4 C3 S1 122.9(2) . . ?
S2 C3 S1 114.24(15) . . ?
C3 C4 S4 123.5(2) . . ?
C3 C4 S3 122.5(2) . . ?
S4 C4 S3 113.98(16) . . ?
C6 C5 C21 128.8(2) . . ?
C6 C5 S3 116.5(2) . . ?
C21 C5 S3 114.7(2) . . ?
C5 C6 C28 130.0(3) . . ?
C5 C6 S4 116.6(2) . . ?
C28 C6 S4 113.1(2) . . ?
C12 C7 C8 118.2(3) . . ?
C12 C7 C1 120.8(3) . . ?
C8 C7 C1 120.9(3) . . ?
C9 C8 C7 121.3(3) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 119.8(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 C13 117.7(3) . . ?
C9 C10 C13 122.9(3) . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 120.7(3) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
O2 C13 O1 124.3(3) . . ?
O2 C13 C10 120.5(3) . . ?
O1 C13 C10 115.3(3) . . ?
C19 C14 C15 119.4(2) . . ?
C19 C14 C2 119.2(3) . . ?
C15 C14 C2 121.4(3) . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 C20 117.4(3) . . ?
C16 C17 C20 122.4(3) . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
O4 C20 O3 124.2(2) . . ?
O4 C20 C17 120.8(3) . . ?
O3 C20 C17 115.0(3) . . ?
C26 C21 C22 118.9(3) . . ?
C26 C21 C5 120.8(3) . . ?
C22 C21 C5 120.3(3) . . ?
C23 C22 C21 120.8(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 119.7(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 119.3(3) . . ?
C25 C24 C27 119.1(3) . . ?
C23 C24 C27 121.6(3) . . ?
C26 C25 C24 120.8(3) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C21 120.3(3) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
O6 C27 O5 124.2(3) . . ?
O6 C27 C24 120.9(3) . . ?
O5 C27 C24 114.9(3) . . ?
C29 C28 C33 118.4(2) . . ?
C29 C28 C6 119.3(2) . . ?
C33 C28 C6 122.2(2) . . ?
C30 C29 C28 120.9(3) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C29 C30 C31 120.1(3) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C30 C31 C32 119.7(2) . . ?
C30 C31 C34 119.2(3) . . ?
C32 C31 C34 121.1(3) . . ?
C33 C32 C31 120.1(3) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C32 C33 C28 120.8(3) . . ?
C32 C33 H33 119.6 . . ?
C28 C33 H33 119.6 . . ?
O8 C34 O7 124.2(2) . . ?
O8 C34 C31 122.5(3) . . ?
O7 C34 C31 113.3(2) . . ?
C36 C35 C40 120.8(3) . . ?
C36 C35 Cl1 120.6(3) . . ?
C40 C35 Cl1 118.6(3) . . ?
C35 C36 C37 119.5(3) . . ?
C35 C36 Cl2 121.2(3) . . ?
C37 C36 Cl2 119.3(3) . . ?
C38 C37 C36 119.9(4) . . ?
C38 C37 H37 120.1 . . ?
C36 C37 H37 120.1 . . ?
C39 C38 C37 120.4(4) . . ?
C39 C38 H38 119.8 . . ?
C37 C38 H38 119.8 . . ?
C40 C39 C38 120.2(4) . . ?
C40 C39 H39 119.9 . . ?
C38 C39 H39 119.9 . . ?
C39 C40 C35 119.3(3) . . ?
C39 C40 H40 120.3 . . ?
C35 C40 H40 120.3 . . ?
C42 C41 C46 119.6(3) . . ?
C42 C41 Cl3 121.1(3) . . ?
C46 C41 Cl3 119.3(3) . . ?
C43 C42 C41 120.6(3) . . ?
C43 C42 Cl4 118.9(3) . . ?
C41 C42 Cl4 120.5(3) . . ?
C42 C43 C44 119.6(4) . . ?
C42 C43 H43 120.2 . . ?
C44 C43 H43 120.2 . . ?
C45 C44 C43 119.2(4) . . ?
C45 C44 H44 120.4 . . ?
C43 C44 H44 120.4 . . ?
C46 C45 C44 121.2(3) . . ?
C46 C45 H45 119.4 . . ?
C44 C45 H45 119.4 . . ?
C45 C46 C41 119.8(4) . . ?
C45 C46 H46 120.1 . . ?
C41 C46 H46 120.1 . . ?
C48 C47 C52 119.9(3) . . ?
C48 C47 Cl6 119.4(3) . . ?
C52 C47 Cl6 120.7(3) . . ?
C49 C48 C47 120.3(3) . . ?
C49 C48 H48 119.8 . . ?
C47 C48 H48 119.8 . . ?
C48 C49 C50 119.7(4) . . ?
C48 C49 H49 120.2 . . ?
C50 C49 H49 120.2 . . ?
C51 C50 C49 120.4(4) . . ?
C51 C50 H50 119.8 . . ?
C49 C50 H50 119.8 . . ?
C50 C51 C52 119.7(3) . . ?
C50 C51 H51 120.1 . . ?
C52 C51 H51 120.1 . . ?
C51 C52 C47 120.1(4) . . ?
C51 C52 Cl5 119.0(3) . . ?
C47 C52 Cl5 120.9(3) . . ?
C58 C53 C54 119.6(5) . . ?
C58 C53 Cl7 119.6(4) . . ?
C54 C53 Cl7 120.8(4) . . ?
C55 C54 C53 120.5(4) . . ?
C55 C54 Cl8 119.8(3) . . ?
C53 C54 Cl8 119.7(4) . . ?
C54 C55 C56 119.0(5) . . ?
C54 C55 H55 120.5 . . ?
C56 C55 H55 120.5 . . ?
C55 C56 C57 120.9(5) . . ?
C55 C56 H56 119.6 . . ?
C57 C56 H56 119.6 . . ?
C58 C57 C56 117.9(4) . . ?
C58 C57 H57 121.1 . . ?
C56 C57 H57 121.1 . . ?
C53 C58 C57 122.2(5) . . ?
C53 C58 H58 118.9 . . ?
C57 C58 H58 118.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 S1 C1 C2 1.8(3) . . . . ?
C3 S1 C1 C7 174.7(2) . . . . ?
C7 C1 C2 C14 3.7(6) . . . . ?
S1 C1 C2 C14 175.4(2) . . . . ?
C7 C1 C2 S2 -169.7(3) . . . . ?
S1 C1 C2 S2 2.0(4) . . . . ?
C3 S2 C2 C1 -4.8(3) . . . . ?
C3 S2 C2 C14 -178.9(2) . . . . ?
C2 S2 C3 C4 -174.9(3) . . . . ?
C2 S2 C3 S1 5.9(2) . . . . ?
C1 S1 C3 C4 175.8(3) . . . . ?
C1 S1 C3 S2 -5.00(19) . . . . ?
S2 C3 C4 S4 -179.60(16) . . . . ?
S1 C3 C4 S4 -0.4(4) . . . . ?
S2 C3 C4 S3 2.6(4) . . . . ?
S1 C3 C4 S3 -178.30(16) . . . . ?
C6 S4 C4 C3 -168.4(3) . . . . ?
C6 S4 C4 S3 9.66(19) . . . . ?
C5 S3 C4 C3 167.5(3) . . . . ?
C5 S3 C4 S4 -10.5(2) . . . . ?
C4 S3 C5 C6 7.6(3) . . . . ?
C4 S3 C5 C21 -172.4(2) . . . . ?
C21 C5 C6 C28 -9.1(6) . . . . ?
S3 C5 C6 C28 170.9(3) . . . . ?
C21 C5 C6 S4 177.9(2) . . . . ?
S3 C5 C6 S4 -2.1(3) . . . . ?
C4 S4 C6 C5 -4.6(3) . . . . ?
C4 S4 C6 C28 -178.8(2) . . . . ?
C2 C1 C7 C12 31.5(5) . . . . ?
S1 C1 C7 C12 -140.4(3) . . . . ?
C2 C1 C7 C8 -151.7(3) . . . . ?
S1 C1 C7 C8 36.4(4) . . . . ?
C12 C7 C8 C9 0.3(5) . . . . ?
C1 C7 C8 C9 -176.5(3) . . . . ?
C7 C8 C9 C10 -0.9(5) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C8 C9 C10 C13 178.0(3) . . . . ?
C9 C10 C11 C12 2.3(5) . . . . ?
C13 C10 C11 C12 -176.2(3) . . . . ?
C10 C11 C12 C7 -2.9(5) . . . . ?
C8 C7 C12 C11 1.6(4) . . . . ?
C1 C7 C12 C11 178.4(3) . . . . ?
C11 C10 C13 O2 -8.4(5) . . . . ?
C9 C10 C13 O2 173.2(3) . . . . ?
C11 C10 C13 O1 171.0(3) . . . . ?
C9 C10 C13 O1 -7.4(5) . . . . ?
C1 C2 C14 C19 -132.3(3) . . . . ?
S2 C2 C14 C19 41.2(4) . . . . ?
C1 C2 C14 C15 45.0(5) . . . . ?
S2 C2 C14 C15 -141.5(3) . . . . ?
C19 C14 C15 C16 6.7(5) . . . . ?
C2 C14 C15 C16 -170.5(3) . . . . ?
C14 C15 C16 C17 -2.9(5) . . . . ?
C15 C16 C17 C18 -2.4(5) . . . . ?
C15 C16 C17 C20 177.2(3) . . . . ?
C16 C17 C18 C19 3.9(5) . . . . ?
C20 C17 C18 C19 -175.7(3) . . . . ?
C17 C18 C19 C14 -0.1(5) . . . . ?
C15 C14 C19 C18 -5.3(5) . . . . ?
C2 C14 C19 C18 172.1(3) . . . . ?
C18 C17 C20 O4 -4.7(5) . . . . ?
C16 C17 C20 O4 175.8(3) . . . . ?
C18 C17 C20 O3 175.7(3) . . . . ?
C16 C17 C20 O3 -3.9(5) . . . . ?
C6 C5 C21 C26 -34.2(5) . . . . ?
S3 C5 C21 C26 145.9(2) . . . . ?
C6 C5 C21 C22 146.9(3) . . . . ?
S3 C5 C21 C22 -33.0(4) . . . . ?
C26 C21 C22 C23 2.4(4) . . . . ?
C5 C21 C22 C23 -178.6(3) . . . . ?
C21 C22 C23 C24 0.5(5) . . . . ?
C22 C23 C24 C25 -2.2(4) . . . . ?
C22 C23 C24 C27 177.5(3) . . . . ?
C23 C24 C25 C26 0.9(4) . . . . ?
C27 C24 C25 C26 -178.7(3) . . . . ?
C24 C25 C26 C21 2.0(4) . . . . ?
C22 C21 C26 C25 -3.7(4) . . . . ?
C5 C21 C26 C25 177.4(3) . . . . ?
C25 C24 C27 O6 11.8(5) . . . . ?
C23 C24 C27 O6 -167.8(3) . . . . ?
C25 C24 C27 O5 -167.8(3) . . . . ?
C23 C24 C27 O5 12.6(4) . . . . ?
C5 C6 C28 C29 153.1(3) . . . . ?
S4 C6 C28 C29 -33.7(4) . . . . ?
C5 C6 C28 C33 -31.8(5) . . . . ?
S4 C6 C28 C33 141.4(3) . . . . ?
C33 C28 C29 C30 1.0(5) . . . . ?
C6 C28 C29 C30 176.3(3) . . . . ?
C28 C29 C30 C31 -0.7(5) . . . . ?
C29 C30 C31 C32 0.0(5) . . . . ?
C29 C30 C31 C34 178.9(3) . . . . ?
C30 C31 C32 C33 0.4(5) . . . . ?
C34 C31 C32 C33 -178.4(3) . . . . ?
C31 C32 C33 C28 -0.1(5) . . . . ?
C29 C28 C33 C32 -0.6(5) . . . . ?
C6 C28 C33 C32 -175.7(3) . . . . ?
C30 C31 C34 O8 -4.8(5) . . . . ?
C32 C31 C34 O8 174.1(3) . . . . ?
C30 C31 C34 O7 175.7(3) . . . . ?
C32 C31 C34 O7 -5.4(4) . . . . ?
C40 C35 C36 C37 0.1(6) . . . . ?
Cl1 C35 C36 C37 -179.3(3) . . . . ?
C40 C35 C36 Cl2 -179.7(3) . . . . ?
Cl1 C35 C36 Cl2 0.8(5) . . . . ?
C35 C36 C37 C38 0.6(6) . . . . ?
Cl2 C36 C37 C38 -179.5(3) . . . . ?
C36 C37 C38 C39 -1.1(6) . . . . ?
C37 C38 C39 C40 0.8(6) . . . . ?
C38 C39 C40 C35 -0.1(6) . . . . ?
C36 C35 C40 C39 -0.4(6) . . . . ?
Cl1 C35 C40 C39 179.1(3) . . . . ?
C46 C41 C42 C43 1.3(6) . . . . ?
Cl3 C41 C42 C43 -178.6(3) . . . . ?
C46 C41 C42 Cl4 -179.3(3) . . . . ?
Cl3 C41 C42 Cl4 0.7(5) . . . . ?
C41 C42 C43 C44 -1.0(6) . . . . ?
Cl4 C42 C43 C44 179.7(3) . . . . ?
C42 C43 C44 C45 0.2(6) . . . . ?
C43 C44 C45 C46 0.2(6) . . . . ?
C44 C45 C46 C41 0.2(6) . . . . ?
C42 C41 C46 C45 -0.9(6) . . . . ?
Cl3 C41 C46 C45 179.0(3) . . . . ?
C52 C47 C48 C49 0.7(5) . . . . ?
Cl6 C47 C48 C49 179.1(3) . . . . ?
C47 C48 C49 C50 -0.1(5) . . . . ?
C48 C49 C50 C51 0.0(6) . . . . ?
C49 C50 C51 C52 -0.4(5) . . . . ?
C50 C51 C52 C47 1.0(5) . . . . ?
C50 C51 C52 Cl5 -176.8(3) . . . . ?
C48 C47 C52 C51 -1.1(5) . . . . ?
Cl6 C47 C52 C51 -179.5(3) . . . . ?
C48 C47 C52 Cl5 176.7(3) . . . . ?
Cl6 C47 C52 Cl5 -1.7(4) . . . . ?
C58 C53 C54 C55 0.1(6) . . . . ?
Cl7 C53 C54 C55 179.3(3) . . . . ?
C58 C53 C54 Cl8 179.9(3) . . . . ?
Cl7 C53 C54 Cl8 -1.0(5) . . . . ?
C53 C54 C55 C56 -0.1(6) . . . . ?
Cl8 C54 C55 C56 -179.9(3) . . . . ?
C54 C55 C56 C57 0.0(6) . . . . ?
C55 C56 C57 C58 0.1(6) . . . . ?
C54 C53 C58 C57 0.0(6) . . . . ?
Cl7 C53 C58 C57 -179.2(3) . . . . ?
C56 C57 C58 C53 -0.1(6) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O6 . . 1_454 2.629(3) 0.820 1.811 176.0 no
O3 H3 O8 . . 1_445 2.635(4) 0.820 1.819 173.7 no
O5 H5 O2 . . 1_656 2.586(4) 0.820 1.767 177.5 no
O7 H7 O4 . . 1_665 2.591(4) 0.820 1.777 171.2 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.




# start Validation Reply Form
_vrf_PLAT029_X-TTF-1_oDCB        
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.899 Note  
RESPONSE:  Diffraction peaks was corrected by DENZO imageprocessing package with 
synchrotron radiation. 
However, the experimental unit we used can enable rotation around the spindle axis only, 
which particularly affects a triclinic crystal such as P-1 crsytal.
;
# end Validation Reply Form

#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMF, o-dichlorobenzene'
####################################################################### 
# 
# 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_X-PyQ-1_oDCB
_database_code_depnum_ccdc_archive 'CCDC 1499635'
_audit_update_record             
;
2017-02-07 deposited with the CCDC.
2017-02-09 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C38 H22 N4 O8'
_chemical_formula_moiety         'C38 H22 N4 O8'
_chemical_formula_weight         662.61
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.60869(10)
_cell_length_b                   14.7726(4)
_cell_length_c                   18.7946(5)
_cell_angle_alpha                75.237(2)
_cell_angle_beta                 82.3657(18)
_cell_angle_gamma                88.5990(19)
_cell_volume                     1492.40(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    8334
_cell_measurement_theta_min      4.41
_cell_measurement_theta_max      75.77
_cell_measurement_temperature    113
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    0.737
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             342.00
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.5a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.573
_exptl_absorpt_correction_T_max  0.957

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      113
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            15411
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_theta_max         76.152
_diffrn_reflns_theta_min         4.411
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5985
_reflns_number_gt                5159
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt)., SQUEEZE
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0765
_refine_ls_wR_factor_ref         0.2723
_refine_ls_wR_factor_gt          0.2660
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5985
_refine_ls_number_parameters     226
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1564P)²+1.0531P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.6245(3) 0.08565(17) 0.43177(11) 0.0607(7) Uani 1 1 d . . . . .
O2 O 1.2564(3) 0.02329(17) 0.44460(10) 0.0591(6) Uani 1 1 d . . . . .
H2O H 1.2968 -0.0081 0.4851 0.071 Uiso 1 1 calc R U . . .
O3 O -0.2437(3) 0.99962(11) -0.05736(10) 0.0397(4) Uani 1 1 d . . . . .
O4 O -0.3811(3) 0.89137(12) 0.04656(10) 0.0398(4) Uani 1 1 d . . . . .
H4O H -0.4909 0.9307 0.0485 0.048 Uiso 1 1 calc R U . . .
N1 N 1.0772(3) 0.36517(12) 0.12728(9) 0.0261(4) Uani 1 1 d . . . . .
N2 N 0.6055(3) 0.61588(12) 0.00534(9) 0.0245(4) Uani 1 1 d . . . . .
C1 C 1.2688(4) 0.31319(14) 0.12401(11) 0.0250(4) Uani 1 1 d . . . . .
C2 C 1.0369(4) 0.43132(14) 0.06395(11) 0.0235(4) Uani 1 1 d . . . . .
C3 C 0.8354(4) 0.48823(14) 0.06602(11) 0.0248(4) Uani 1 1 d . . . . .
H3 H 0.7254 0.4804 0.1102 0.030 Uiso 1 1 calc R U . . .
C4 C 0.7974(3) 0.55694(14) 0.00223(11) 0.0235(4) Uani 1 1 d . . . . .
C5 C 0.5730(4) 0.68033(14) -0.05497(11) 0.0241(4) Uani 1 1 d . . . . .
C6 C 1.3133(4) 0.25062(15) 0.19731(11) 0.0278(5) Uani 1 1 d . . . . .
C7 C 1.1414(4) 0.18375(17) 0.23658(13) 0.0349(5) Uani 1 1 d . . . . .
H7 H 0.9998 0.1762 0.2159 0.042 Uiso 1 1 calc R U . . .
C8 C 1.1763(4) 0.12835(19) 0.30559(13) 0.0403(6) Uani 1 1 d . . . . .
H8 H 1.0600 0.0822 0.3322 0.048 Uiso 1 1 calc R U . . .
C9 C 1.3830(4) 0.14069(18) 0.33584(12) 0.0362(5) Uani 1 1 d . . . . .
C10 C 1.5531(4) 0.20817(17) 0.29690(12) 0.0346(5) Uani 1 1 d . . . . .
H10 H 1.6927 0.2169 0.3181 0.042 Uiso 1 1 calc R U . . .
C11 C 1.5201(4) 0.26294(16) 0.22713(12) 0.0313(5) Uani 1 1 d . . . . .
H11 H 1.6376 0.3084 0.2001 0.038 Uiso 1 1 calc R U . . .
C12 C 1.4304(4) 0.0802(2) 0.40905(13) 0.0423(6) Uani 1 1 d . . . . .
C13 C 0.3698(4) 0.74551(14) -0.04604(11) 0.0246(4) Uani 1 1 d . . . . .
C14 C 0.1850(4) 0.71459(15) 0.01229(12) 0.0277(4) Uani 1 1 d . . . . .
H14 H 0.1920 0.6536 0.0442 0.033 Uiso 1 1 calc R U . . .
C15 C -0.0084(4) 0.77158(15) 0.02426(12) 0.0291(5) Uani 1 1 d . . . . .
H15 H -0.1333 0.7496 0.0640 0.035 Uiso 1 1 calc R U . . .
C16 C -0.0187(4) 0.86148(15) -0.02234(12) 0.0285(5) Uani 1 1 d . . . . .
C17 C 0.1676(4) 0.89351(15) -0.07965(12) 0.0301(5) Uani 1 1 d . . . . .
H17 H 0.1621 0.9550 -0.1109 0.036 Uiso 1 1 calc R U . . .
C18 C 0.3598(4) 0.83684(15) -0.09141(12) 0.0289(4) Uani 1 1 d . . . . .
H18 H 0.4864 0.8597 -0.1304 0.035 Uiso 1 1 calc R U . . .
C19 C -0.2266(4) 0.92287(15) -0.01136(13) 0.0311(5) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.5a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.5a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.5a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.233(3) . ?
O2 C12 1.299(3) . ?
O2 H2O 0.8400 . ?
O3 C19 1.249(3) . ?
O4 C19 1.290(3) . ?
O4 H4O 0.8400 . ?
N1 C1 1.310(3) . ?
N1 C2 1.375(2) . ?
N2 C5 1.312(3) . ?
N2 C4 1.373(3) . ?
C1 C5 1.454(3) 2_765 ?
C1 C6 1.498(3) . ?
C2 C3 1.394(3) . ?
C2 C4 1.425(3) 2_765 ?
C3 C4 1.397(3) . ?
C3 H3 0.9500 . ?
C4 C2 1.425(3) 2_765 ?
C5 C1 1.454(3) 2_765 ?
C5 C13 1.494(3) . ?
C6 C11 1.388(3) . ?
C6 C7 1.391(3) . ?
C7 C8 1.382(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(3) . ?
C9 C12 1.490(3) . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C13 C14 1.397(3) . ?
C13 C18 1.405(3) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.397(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(3) . ?
C16 C19 1.485(3) . ?
C17 C18 1.378(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

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
C12 O2 H2O 109.5 . . ?
C19 O4 H4O 109.5 . . ?
C1 N1 C2 117.83(17) . . ?
C5 N2 C4 118.27(17) . . ?
N1 C1 C5 121.86(17) . 2_765 ?
N1 C1 C6 114.18(17) . . ?
C5 C1 C6 123.92(17) 2_765 . ?
N1 C2 C3 119.05(18) . . ?
N1 C2 C4 120.32(18) . 2_765 ?
C3 C2 C4 120.60(18) . 2_765 ?
C2 C3 C4 119.11(18) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
N2 C4 C3 119.05(18) . . ?
N2 C4 C2 120.58(18) . 2_765 ?
C3 C4 C2 120.29(18) . 2_765 ?
N2 C5 C1 120.78(18) . 2_765 ?
N2 C5 C13 115.16(17) . . ?
C1 C5 C13 124.05(17) 2_765 . ?
C11 C6 C7 120.54(19) . . ?
C11 C6 C1 119.70(19) . . ?
C7 C6 C1 119.69(19) . . ?
C8 C7 C6 120.1(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 119.6(2) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 C12 118.7(2) . . ?
C8 C9 C12 121.0(2) . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C6 119.3(2) . . ?
C10 C11 H11 120.4 . . ?
C6 C11 H11 120.4 . . ?
O1 C12 O2 124.4(2) . . ?
O1 C12 C9 120.3(2) . . ?
O2 C12 C9 115.3(2) . . ?
C14 C13 C18 118.68(18) . . ?
C14 C13 C5 117.83(17) . . ?
C18 C13 C5 123.45(19) . . ?
C15 C14 C13 120.98(19) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 119.7(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 119.60(19) . . ?
C17 C16 C19 119.88(19) . . ?
C15 C16 C19 120.5(2) . . ?
C18 C17 C16 120.62(19) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C13 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
O3 C19 O4 124.22(19) . . ?
O3 C19 C16 119.7(2) . . ?
O4 C19 C16 116.08(19) . . ?

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
C2 N1 C1 C5 -4.2(3) . . . 2_765 ?
C2 N1 C1 C6 173.53(19) . . . . ?
C1 N1 C2 C3 -179.4(2) . . . . ?
C1 N1 C2 C4 -1.1(3) . . . 2_765 ?
N1 C2 C3 C4 178.5(2) . . . . ?
C4 C2 C3 C4 0.1(4) 2_765 . . . ?
C5 N2 C4 C3 179.66(19) . . . . ?
C5 N2 C4 C2 2.9(3) . . . 2_765 ?
C2 C3 C4 N2 -176.87(19) . . . . ?
C2 C3 C4 C2 -0.1(4) . . . 2_765 ?
C4 N2 C5 C1 2.3(3) . . . 2_765 ?
C4 N2 C5 C13 -176.36(18) . . . . ?
N1 C1 C6 C11 -116.6(2) . . . . ?
C5 C1 C6 C11 61.1(3) 2_765 . . . ?
N1 C1 C6 C7 60.3(3) . . . . ?
C5 C1 C6 C7 -122.1(2) 2_765 . . . ?
C11 C6 C7 C8 -0.5(4) . . . . ?
C1 C6 C7 C8 -177.3(2) . . . . ?
C6 C7 C8 C9 0.8(4) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C7 C8 C9 C12 -178.1(2) . . . . ?
C8 C9 C10 C11 -0.9(4) . . . . ?
C12 C9 C10 C11 177.2(2) . . . . ?
C9 C10 C11 C6 1.1(4) . . . . ?
C7 C6 C11 C10 -0.4(3) . . . . ?
C1 C6 C11 C10 176.4(2) . . . . ?
C10 C9 C12 O1 -5.2(4) . . . . ?
C8 C9 C12 O1 172.8(3) . . . . ?
C10 C9 C12 O2 175.4(2) . . . . ?
C8 C9 C12 O2 -6.6(4) . . . . ?
N2 C5 C13 C14 -23.3(3) . . . . ?
C1 C5 C13 C14 158.2(2) 2_765 . . . ?
N2 C5 C13 C18 154.4(2) . . . . ?
C1 C5 C13 C18 -24.2(3) 2_765 . . . ?
C18 C13 C14 C15 1.8(3) . . . . ?
C5 C13 C14 C15 179.52(19) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C17 -1.1(3) . . . . ?
C14 C15 C16 C19 178.8(2) . . . . ?
C15 C16 C17 C18 1.0(3) . . . . ?
C19 C16 C17 C18 -178.9(2) . . . . ?
C16 C17 C18 C13 0.5(3) . . . . ?
C14 C13 C18 C17 -1.8(3) . . . . ?
C5 C13 C18 C17 -179.5(2) . . . . ?
C17 C16 C19 O3 6.2(3) . . . . ?
C15 C16 C19 O3 -173.6(2) . . . . ?
C17 C16 C19 O4 -174.2(2) . . . . ?
C15 C16 C19 O4 5.9(3) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2O O1 . . 2_856 2.625(3) 0.840 1.788 174.0 no
O4 H4O O3 . . 2_475 2.636(2) 0.840 1.803 171.5 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMF, o-dichlorobenzene'
####################################################################### 
# 
# 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_X-Ph-1_oDCB
_database_code_depnum_ccdc_archive 'CCDC 1499633'
_audit_update_record             
;
2017-02-07 deposited with the CCDC.
2017-02-09 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C34 H22 O8'
_chemical_formula_moiety         'C34 H22 O8'
_chemical_formula_weight         558.54
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
_space_group_IT_number           60
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,+Y,1/2-Z
5 -X,-Y,-Z
6 -1/2+X,-1/2+Y,-1/2-Z
7 -1/2-X,-1/2+Y,+Z
8 +X,-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   19.4377(15)
_cell_length_b                   30.6822(12)
_cell_length_c                   9.1127(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     5434.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2513
_cell_measurement_theta_min      5.37
_cell_measurement_theta_max      74.89
_cell_measurement_temperature    253
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    0.683
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160.00
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.5a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.176
_exptl_absorpt_correction_T_max  0.980

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      253
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_reflns_number            13201
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_theta_max         76.920
_diffrn_reflns_theta_min         4.550
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5384
_reflns_number_gt                2286
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt)., SQUEEZE
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1720
_refine_ls_R_factor_gt           0.1026
_refine_ls_wR_factor_ref         0.3439
_refine_ls_wR_factor_gt          0.3133
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5384
_refine_ls_number_parameters     190
_refine_ls_goodness_of_fit_ref   1.360
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1300P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7419(2) 0.36247(9) 0.1652(4) 0.0822(11) Uani 1 1 d . . . . .
O2 O 0.6847(2) 0.33956(9) 0.3597(4) 0.1092(16) Uani 1 1 d . . . . .
H2O H 0.7130 0.3199 0.3545 0.131 Uiso 1 1 calc R U . . .
O3 O 0.7434(2) 0.76714(10) 0.3568(5) 0.1142(16) Uani 1 1 d . . . . .
O4 O 0.6883(2) 0.78982(9) 0.1583(4) 0.0949(13) Uani 1 1 d . . . . .
H4O H 0.7145 0.8106 0.1679 0.114 Uiso 1 1 calc R U . . .
C1 C 0.53566(17) 0.52514(8) 0.2552(4) 0.0402(9) Uani 1 1 d . . . . .
C2 C 0.57020(19) 0.56537(8) 0.2598(4) 0.0429(9) Uani 1 1 d . . . . .
H2 H 0.6179 0.5654 0.2666 0.051 Uiso 1 1 calc R U . . .
C3 C 0.53580(17) 0.60541(8) 0.2545(4) 0.0409(9) Uani 1 1 d . . . . .
C4 C 0.57739(19) 0.48435(8) 0.2604(4) 0.0410(9) Uani 1 1 d . . . . .
C5 C 0.6317(2) 0.47865(10) 0.1623(5) 0.0506(11) Uani 1 1 d . . . . .
H5 H 0.6421 0.5005 0.0951 0.061 Uiso 1 1 calc R U . . .
C6 C 0.6701(2) 0.44079(10) 0.1643(5) 0.0545(12) Uani 1 1 d . . . . .
H6 H 0.7060 0.4372 0.0979 0.065 Uiso 1 1 calc R U . . .
C7 C 0.6557(2) 0.40842(10) 0.2632(5) 0.0510(11) Uani 1 1 d . . . . .
C8 C 0.6034(2) 0.41397(10) 0.3624(5) 0.0562(12) Uani 1 1 d . . . . .
H8 H 0.5942 0.3923 0.4309 0.067 Uiso 1 1 calc R U . . .
C9 C 0.5642(2) 0.45159(8) 0.3615(4) 0.0448(10) Uani 1 1 d . . . . .
H9 H 0.5287 0.4549 0.4290 0.054 Uiso 1 1 calc R U . . .
C10 C 0.6968(3) 0.36753(11) 0.2606(6) 0.0647(13) Uani 1 1 d . . . . .
C11 C 0.57823(19) 0.64605(9) 0.2557(5) 0.0458(10) Uani 1 1 d . . . . .
C12 C 0.6286(2) 0.65187(10) 0.3608(5) 0.0602(13) Uani 1 1 d . . . . .
H12 H 0.6356 0.6307 0.4324 0.072 Uiso 1 1 calc R U . . .
C13 C 0.6690(2) 0.68936(10) 0.3598(6) 0.0704(15) Uani 1 1 d . . . . .
H13 H 0.7027 0.6934 0.4311 0.084 Uiso 1 1 calc R U . . .
C14 C 0.6590(2) 0.72086(10) 0.2518(5) 0.0599(12) Uani 1 1 d . . . . .
C15 C 0.6083(2) 0.71487(10) 0.1445(5) 0.0575(12) Uani 1 1 d . . . . .
H15 H 0.6016 0.7357 0.0718 0.069 Uiso 1 1 calc R U . . .
C16 C 0.5685(2) 0.67781(9) 0.1478(5) 0.0497(11) Uani 1 1 d . . . . .
H16 H 0.5346 0.6738 0.0771 0.060 Uiso 1 1 calc R U . . .
C17 C 0.7007(3) 0.76169(11) 0.2568(6) 0.0703(14) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.5a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.5a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.5a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXD Version 2013/2 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.245(5) . ?
O2 C10 1.268(5) . ?
O2 H2O 0.8200 . ?
O3 C17 1.244(6) . ?
O4 C17 1.269(5) . ?
O4 H4O 0.8200 . ?
C1 C1 1.389(7) 4_655 ?
C1 C2 1.406(4) . ?
C1 C4 1.492(4) . ?
C2 C3 1.400(4) . ?
C2 H2 0.9300 . ?
C3 C3 1.394(6) 4_655 ?
C3 C11 1.495(4) . ?
C4 C9 1.387(4) . ?
C4 C5 1.394(5) . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.370(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.371(6) . ?
C7 C10 1.487(5) . ?
C8 C9 1.384(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C11 C12 1.382(5) . ?
C11 C16 1.397(5) . ?
C12 C13 1.393(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.393(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.400(6) . ?
C14 C17 1.493(5) . ?
C15 C16 1.376(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O2 H2O 109.5 . . ?
C17 O4 H4O 109.5 . . ?
C1 C1 C2 118.59(19) 4_655 . ?
C1 C1 C4 122.99(18) 4_655 . ?
C2 C1 C4 118.4(3) . . ?
C3 C2 C1 122.8(3) . . ?
C3 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
C3 C3 C2 118.62(18) 4_655 . ?
C3 C3 C11 123.45(18) 4_655 . ?
C2 C3 C11 117.9(3) . . ?
C9 C4 C5 118.4(3) . . ?
C9 C4 C1 121.9(3) . . ?
C5 C4 C1 119.7(3) . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.5(4) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 C10 119.4(4) . . ?
C8 C7 C10 120.9(3) . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 120.4(4) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
O1 C10 O2 123.0(4) . . ?
O1 C10 C7 119.6(4) . . ?
O2 C10 C7 117.4(4) . . ?
C12 C11 C16 119.6(3) . . ?
C12 C11 C3 120.2(3) . . ?
C16 C11 C3 120.1(4) . . ?
C11 C12 C13 120.1(4) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 120.0(4) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 C17 119.0(4) . . ?
C15 C14 C17 120.9(4) . . ?
C16 C15 C14 119.3(4) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C11 121.1(4) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
O3 C17 O4 123.6(4) . . ?
O3 C17 C14 119.8(4) . . ?
O4 C17 C14 116.5(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
C1 C1 C2 C3 0.0(7) 4_655 . . . ?
C4 C1 C2 C3 179.6(4) . . . . ?
C1 C2 C3 C3 0.5(7) . . . 4_655 ?
C1 C2 C3 C11 -178.2(4) . . . . ?
C1 C1 C4 C9 -53.1(7) 4_655 . . . ?
C2 C1 C4 C9 127.4(4) . . . . ?
C1 C1 C4 C5 127.3(5) 4_655 . . . ?
C2 C1 C4 C5 -52.2(5) . . . . ?
C9 C4 C5 C6 1.5(6) . . . . ?
C1 C4 C5 C6 -179.0(4) . . . . ?
C4 C5 C6 C7 -0.4(6) . . . . ?
C5 C6 C7 C8 -1.0(6) . . . . ?
C5 C6 C7 C10 178.6(4) . . . . ?
C6 C7 C8 C9 1.3(6) . . . . ?
C10 C7 C8 C9 -178.2(4) . . . . ?
C7 C8 C9 C4 -0.3(6) . . . . ?
C5 C4 C9 C8 -1.1(6) . . . . ?
C1 C4 C9 C8 179.3(3) . . . . ?
C6 C7 C10 O1 -2.8(7) . . . . ?
C8 C7 C10 O1 176.8(4) . . . . ?
C6 C7 C10 O2 175.7(5) . . . . ?
C8 C7 C10 O2 -4.8(7) . . . . ?
C3 C3 C11 C12 130.8(5) 4_655 . . . ?
C2 C3 C11 C12 -50.5(6) . . . . ?
C3 C3 C11 C16 -51.1(7) 4_655 . . . ?
C2 C3 C11 C16 127.6(4) . . . . ?
C16 C11 C12 C13 0.5(7) . . . . ?
C3 C11 C12 C13 178.7(4) . . . . ?
C11 C12 C13 C14 -0.6(7) . . . . ?
C12 C13 C14 C15 0.1(7) . . . . ?
C12 C13 C14 C17 177.2(4) . . . . ?
C13 C14 C15 C16 0.4(7) . . . . ?
C17 C14 C15 C16 -176.7(4) . . . . ?
C14 C15 C16 C11 -0.4(6) . . . . ?
C12 C11 C16 C15 0.0(6) . . . . ?
C3 C11 C16 C15 -178.2(4) . . . . ?
C13 C14 C17 O3 -0.2(7) . . . . ?
C15 C14 C17 O3 176.9(5) . . . . ?
C13 C14 C17 O4 -178.2(5) . . . . ?
C15 C14 C17 O4 -1.1(7) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2O O3 . . 7_755 2.625(5) 0.820 1.825 164.7 no
O4 H4O O1 . . 7_765 2.610(4) 0.820 1.804 167.2 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMF, o-dichlorobenzene'
