# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_marcoc3a
_database_code_depnum_ccdc_archive 'CCDC 1497840'
_audit_update_record             
;
2016-08-05 deposited with the CCDC.
2016-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_structural     
'C6H4-1,4-{CH(C6H2-2,4-(OH)2,-Cl-5)2}2, 6(Et2O)'
_chemical_formula_moiety         'C32 H22 Cl4 O8, 6(C4 H10 O)'
_chemical_formula_sum            'C56 H82 Cl4 O14'
_chemical_formula_weight         1121.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   19.5798(5)
_cell_length_b                   10.5855(2)
_cell_length_c                   30.2255(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.449(2)
_cell_angle_gamma                90
_cell_volume                     6160.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    12398
_cell_measurement_theta_min      3.0230
_cell_measurement_theta_max      32.6440

_exptl_crystal_description       block
_exptl_crystal_colour            'pale brown'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_F_000             2392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.251
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
 CrysAlisPro, Agilent Technologies, Version 1.171.36.21 
 Empirical absorption correction using spherical harmonics,
  implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      140(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur 3/Sapphire3 CCD'
_diffrn_measurement_method       'Thin slice φ and ω scans'
_diffrn_detector_area_resol_mean 16.0050
_diffrn_reflns_number            50395
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         3.029
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7083
_reflns_number_gt                5801
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies, Version 1.171.36.21 
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies, Version 1.171.36.21 
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies, Version 1.171.36.21 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976 and Farrugia, 2012)'
_computing_publication_material  
'SHELXL-2014/7 (Sheldrick, 2014) and WINGX (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+4.2476P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7083
_refine_ls_number_parameters     498
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0993
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.37079(7) 0.86947(11) 0.57330(4) 0.0171(3) Uani 1 1 d . . . . .
C11 C 0.39290(7) 0.73297(12) 0.58317(4) 0.0171(3) Uani 1 1 d . . . . .
C12 C 0.46187(7) 0.70907(12) 0.60343(4) 0.0196(3) Uani 1 1 d . . . . .
O12 O 0.50291(5) 0.81141(9) 0.61608(4) 0.0264(2) Uani 1 1 d . . . . .
C13 C 0.48632(7) 0.58603(13) 0.61035(5) 0.0231(3) Uani 1 1 d . . . . .
C14 C 0.44243(7) 0.48390(12) 0.59731(5) 0.0216(3) Uani 1 1 d . . . . .
O14 O 0.46528(6) 0.36164(9) 0.60274(4) 0.0309(3) Uani 1 1 d . . . . .
C15 C 0.37364(7) 0.50718(12) 0.57855(5) 0.0206(3) Uani 1 1 d . . . . .
Cl15 Cl 0.31758(2) 0.38161(3) 0.56152(2) 0.03073(10) Uani 1 1 d . . . . .
C16 C 0.34939(7) 0.63008(12) 0.57148(4) 0.0195(3) Uani 1 1 d . . . . .
C21 C 0.36320(7) 0.94102(12) 0.61579(4) 0.0170(3) Uani 1 1 d . . . . .
C22 C 0.38563(7) 1.06678(12) 0.62092(4) 0.0198(3) Uani 1 1 d . . . . .
O22 O 0.41243(6) 1.11826(10) 0.58655(4) 0.0289(2) Uani 1 1 d . . . . .
C23 C 0.38098(7) 1.13432(13) 0.65973(5) 0.0226(3) Uani 1 1 d . . . . .
C24 C 0.35298(7) 1.07891(13) 0.69420(4) 0.0221(3) Uani 1 1 d . . . . .
O24 O 0.34734(6) 1.14199(11) 0.73263(4) 0.0313(2) Uani 1 1 d . . . . .
C25 C 0.33006(7) 0.95445(13) 0.68899(5) 0.0225(3) Uani 1 1 d . . . . .
C26 C 0.33586(7) 0.88685(12) 0.65044(4) 0.0200(3) Uani 1 1 d . . . . .
Cl25 Cl 0.29505(2) 0.88108(4) 0.73144(2) 0.03853(11) Uani 1 1 d . . . . .
C31 C 0.30752(7) 0.87874(11) 0.53581(4) 0.0177(3) Uani 1 1 d . . . . .
C32 C 0.31673(7) 0.87936(13) 0.49131(5) 0.0218(3) Uani 1 1 d . . . . .
C36 C 0.23979(7) 0.88005(13) 0.54412(5) 0.0223(3) Uani 1 1 d . . . . .
O4 O 0.60083(6) 0.32692(12) 0.60356(4) 0.0415(3) Uani 1 1 d . . . . .
C41 C 0.63998(12) 0.4162(2) 0.58279(9) 0.0575(6) Uani 1 1 d . . . . .
C42 C 0.60106(19) 0.4466(2) 0.53753(9) 0.0723(8) Uani 1 1 d . . . . .
C43 C 0.63742(13) 0.2738(3) 0.64437(8) 0.0694(7) Uani 1 1 d . . . . .
C44 C 0.5968(2) 0.1665(5) 0.65763(15) 0.1124(16) Uani 1 1 d . . . . .
O5 O 0.63062(6) 0.78910(12) 0.59791(4) 0.0369(3) Uani 1 1 d . . . . .
C51 C 0.63940(11) 0.8059(2) 0.55252(7) 0.0476(5) Uani 1 1 d . . . . .
C52 C 0.57039(14) 0.8126(3) 0.52258(7) 0.0646(7) Uani 1 1 d . . . . .
C53 C 0.69176(9) 0.8116(2) 0.63036(6) 0.0431(4) Uani 1 1 d . . . . .
C54 C 0.67494(11) 0.7963(3) 0.67622(7) 0.0563(6) Uani 1 1 d . . . . .
O6 O 0.40841(6) 1.37907(10) 0.73061(4) 0.0366(3) Uani 1 1 d . . . . .
C61 C 0.47773(11) 1.39459(19) 0.75427(9) 0.0519(5) Uani 1 1 d . . . . .
C62 C 0.50742(11) 1.2683(2) 0.76856(8) 0.0522(5) Uani 1 1 d . . . . .
C63 C 0.37684(11) 1.49584(17) 0.71340(7) 0.0455(4) Uani 1 1 d . . . . .
C64 C 0.30553(12) 1.4706(2) 0.68868(8) 0.0504(5) Uani 1 1 d . . . . .
H1 H 0.4085(8) 0.9082(14) 0.5611(5) 0.017(4) Uiso 1 1 d . . . . .
H12 H 0.5429(12) 0.795(2) 0.6127(7) 0.056(7) Uiso 1 1 d . . . . .
H13 H 0.5318(9) 0.5724(16) 0.6243(5) 0.026(4) Uiso 1 1 d . . . . .
H14 H 0.5076(13) 0.358(2) 0.6042(8) 0.060(7) Uiso 1 1 d . . . . .
H16 H 0.3012(9) 0.6445(15) 0.5572(5) 0.023(4) Uiso 1 1 d . . . . .
H22 H 0.4206(10) 1.184(2) 0.5913(6) 0.037(6) Uiso 1 1 d . . . . .
H23 H 0.3954(8) 1.2203(16) 0.6616(5) 0.026(4) Uiso 1 1 d . . . . .
H24 H 0.3630(11) 1.213(2) 0.7302(7) 0.046(6) Uiso 1 1 d . . . . .
H26 H 0.3211(8) 0.7999(15) 0.6491(5) 0.019(4) Uiso 1 1 d . . . . .
H32 H 0.3639(9) 0.8791(14) 0.4851(5) 0.022(4) Uiso 1 1 d . . . . .
H36 H 0.2316(9) 0.8824(15) 0.5739(6) 0.031(4) Uiso 1 1 d . . . . .
H41A H 0.6476(13) 0.494(3) 0.6026(9) 0.076(8) Uiso 1 1 d . . . . .
H41B H 0.6837(14) 0.376(2) 0.5815(8) 0.073(8) Uiso 1 1 d . . . . .
H42A H 0.6271(14) 0.503(3) 0.5210(9) 0.080(8) Uiso 1 1 d . . . . .
H42B H 0.5564(13) 0.483(2) 0.5384(8) 0.067(7) Uiso 1 1 d . . . . .
H42C H 0.5897(15) 0.366(3) 0.5187(9) 0.092(9) Uiso 1 1 d . . . . .
H43A H 0.6853(16) 0.247(3) 0.6407(10) 0.101(10) Uiso 1 1 d . . . . .
H43B H 0.6423(15) 0.344(3) 0.6646(10) 0.087(9) Uiso 1 1 d . . . . .
H44A H 0.618(2) 0.127(3) 0.6811(13) 0.128(13) Uiso 1 1 d . . . . .
H44B H 0.559(2) 0.217(4) 0.6685(14) 0.156(17) Uiso 1 1 d . . . . .
H44C H 0.585(2) 0.102(4) 0.6291(16) 0.162(19) Uiso 1 1 d . . . . .
H51A H 0.6660(13) 0.880(2) 0.5505(8) 0.065(7) Uiso 1 1 d . . . . .
H51B H 0.6695(14) 0.730(3) 0.5449(9) 0.083(8) Uiso 1 1 d . . . . .
H52A H 0.5437(13) 0.738(2) 0.5233(8) 0.064(7) Uiso 1 1 d . . . . .
H52B H 0.5771(15) 0.827(3) 0.4926(10) 0.094(9) Uiso 1 1 d . . . . .
H52C H 0.5421(16) 0.889(3) 0.5306(10) 0.090(9) Uiso 1 1 d . . . . .
H53A H 0.7297(12) 0.755(2) 0.6246(7) 0.059(6) Uiso 1 1 d . . . . .
H53B H 0.7089(13) 0.900(2) 0.6254(8) 0.068(7) Uiso 1 1 d . . . . .
H54A H 0.7160(14) 0.815(2) 0.6991(8) 0.076(8) Uiso 1 1 d . . . . .
H54B H 0.6555(13) 0.708(2) 0.6791(8) 0.068(7) Uiso 1 1 d . . . . .
H54C H 0.6388(15) 0.860(3) 0.6801(9) 0.080(8) Uiso 1 1 d . . . . .
H61A H 0.5034(13) 1.436(2) 0.7345(8) 0.068(7) Uiso 1 1 d . . . . .
H61B H 0.4774(13) 1.452(3) 0.7797(8) 0.073(7) Uiso 1 1 d . . . . .
H62A H 0.5551(13) 1.274(2) 0.7838(8) 0.069(7) Uiso 1 1 d . . . . .
H62B H 0.5051(11) 1.214(2) 0.7422(7) 0.055(6) Uiso 1 1 d . . . . .
H62C H 0.4804(13) 1.226(2) 0.7895(8) 0.069(7) Uiso 1 1 d . . . . .
H63A H 0.4056(12) 1.539(2) 0.6913(8) 0.070(7) Uiso 1 1 d . . . . .
H63B H 0.3741(11) 1.553(2) 0.7396(7) 0.053(6) Uiso 1 1 d . . . . .
H64A H 0.2837(13) 1.551(3) 0.6767(8) 0.072(7) Uiso 1 1 d . . . . .
H64B H 0.2804(12) 1.433(2) 0.7090(8) 0.060(7) Uiso 1 1 d . . . . .
H64C H 0.3077(11) 1.417(2) 0.6630(8) 0.054(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C21 1.5213(18) . ?
C1 C11 1.5223(17) . ?
C1 C31 1.5229(17) . ?
C1 H1 0.973(16) . ?
C11 C16 1.3884(18) . ?
C11 C12 1.4009(18) . ?
C12 O12 1.3616(16) . ?
C12 C13 1.3903(19) . ?
O12 H12 0.83(2) . ?
C13 C14 1.3927(19) . ?
C13 H13 0.925(17) . ?
C14 O14 1.3695(16) . ?
C14 C15 1.3855(19) . ?
O14 H14 0.82(2) . ?
C15 C16 1.3880(18) . ?
C15 Cl15 1.7412(13) . ?
C16 H16 0.977(17) . ?
C21 C26 1.3843(19) . ?
C21 C22 1.4015(18) . ?
C22 O22 1.3597(17) . ?
C22 C23 1.3909(19) . ?
O22 H22 0.72(2) . ?
C23 C24 1.392(2) . ?
C23 H23 0.951(17) . ?
C24 O24 1.3615(17) . ?
C24 C25 1.392(2) . ?
O24 H24 0.82(2) . ?
C25 C26 1.3895(19) . ?
C25 Cl25 1.7431(14) . ?
C26 H26 0.963(16) . ?
C31 C32 1.3890(19) . ?
C31 C36 1.3937(19) . ?
C32 C36 1.3936(19) 2_556 ?
C32 H32 0.975(17) . ?
C36 C32 1.3936(19) 2_556 ?
C36 H36 0.942(18) . ?
O4 C43 1.425(3) . ?
O4 C41 1.432(2) . ?
C41 C42 1.476(4) . ?
C41 H41A 1.02(3) . ?
C41 H41B 0.96(3) . ?
C42 H42A 0.98(3) . ?
C42 H42B 0.96(3) . ?
C42 H42C 1.03(3) . ?
C43 C44 1.482(5) . ?
C43 H43A 1.00(3) . ?
C43 H43B 0.95(3) . ?
C44 H44A 0.86(4) . ?
C44 H44B 1.01(5) . ?
C44 H44C 1.09(4) . ?
O5 C53 1.423(2) . ?
O5 C51 1.424(2) . ?
C51 C52 1.485(3) . ?
C51 H51A 0.95(2) . ?
C51 H51B 1.04(3) . ?
C52 H52A 0.94(3) . ?
C52 H52B 0.95(3) . ?
C52 H52C 1.03(3) . ?
C53 C54 1.490(3) . ?
C53 H53A 0.99(2) . ?
C53 H53B 1.01(3) . ?
C54 H54A 0.98(3) . ?
C54 H54B 1.02(3) . ?
C54 H54C 1.00(3) . ?
O6 C61 1.424(2) . ?
O6 C63 1.437(2) . ?
C61 C62 1.490(3) . ?
C61 H61A 0.95(3) . ?
C61 H61B 0.98(3) . ?
C62 H62A 0.97(3) . ?
C62 H62B 0.98(2) . ?
C62 H62C 1.00(3) . ?
C63 C64 1.484(3) . ?
C63 H63A 1.05(3) . ?
C63 H63B 1.00(2) . ?
C64 H64A 0.99(3) . ?
C64 H64B 0.94(2) . ?
C64 H64C 0.97(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
C21 C1 C11 112.02(10) . . ?
C21 C1 C31 113.90(10) . . ?
C11 C1 C31 111.79(10) . . ?
C21 C1 H1 107.9(9) . . ?
C11 C1 H1 105.4(9) . . ?
C31 C1 H1 105.1(9) . . ?
C16 C11 C12 117.90(12) . . ?
C16 C11 C1 123.72(11) . . ?
C12 C11 C1 118.32(11) . . ?
O12 C12 C13 122.25(12) . . ?
O12 C12 C11 116.87(11) . . ?
C13 C12 C11 120.88(12) . . ?
C12 O12 H12 109.0(16) . . ?
C12 C13 C14 120.44(13) . . ?
C12 C13 H13 119.4(10) . . ?
C14 C13 H13 120.1(10) . . ?
O14 C14 C15 119.30(12) . . ?
O14 C14 C13 121.89(12) . . ?
C15 C14 C13 118.81(12) . . ?
C14 O14 H14 110.9(16) . . ?
C14 C15 C16 120.65(12) . . ?
C14 C15 Cl15 119.95(10) . . ?
C16 C15 Cl15 119.36(10) . . ?
C15 C16 C11 121.27(12) . . ?
C15 C16 H16 119.4(9) . . ?
C11 C16 H16 119.3(9) . . ?
C26 C21 C22 117.79(12) . . ?
C26 C21 C1 122.89(11) . . ?
C22 C21 C1 119.32(12) . . ?
O22 C22 C23 122.12(12) . . ?
O22 C22 C21 116.92(12) . . ?
C23 C22 C21 120.96(13) . . ?
C22 O22 H22 109.7(16) . . ?
C22 C23 C24 120.65(13) . . ?
C22 C23 H23 118.5(10) . . ?
C24 C23 H23 120.8(10) . . ?
O24 C24 C25 119.10(13) . . ?
O24 C24 C23 122.40(13) . . ?
C25 C24 C23 118.49(12) . . ?
C24 O24 H24 106.3(15) . . ?
C26 C25 C24 120.58(13) . . ?
C26 C25 Cl25 119.39(11) . . ?
C24 C25 Cl25 120.03(11) . . ?
C21 C26 C25 121.53(12) . . ?
C21 C26 H26 121.3(9) . . ?
C25 C26 H26 117.2(9) . . ?
C32 C31 C36 117.99(12) . . ?
C32 C31 C1 119.32(12) . . ?
C36 C31 C1 122.60(12) . . ?
C31 C32 C36 121.31(13) . 2_556 ?
C31 C32 H32 118.7(9) . . ?
C36 C32 H32 120.0(9) 2_556 . ?
C32 C36 C31 120.69(13) 2_556 . ?
C32 C36 H36 119.0(11) 2_556 . ?
C31 C36 H36 120.3(11) . . ?
C43 O4 C41 114.53(19) . . ?
O4 C41 C42 108.8(2) . . ?
O4 C41 H41A 108.2(15) . . ?
C42 C41 H41A 111.4(14) . . ?
O4 C41 H41B 106.1(15) . . ?
C42 C41 H41B 111.8(15) . . ?
H41A C41 H41B 110(2) . . ?
C41 C42 H42A 112.2(15) . . ?
C41 C42 H42B 112.5(15) . . ?
H42A C42 H42B 109(2) . . ?
C41 C42 H42C 110.9(16) . . ?
H42A C42 H42C 108(2) . . ?
H42B C42 H42C 104(2) . . ?
O4 C43 C44 109.0(2) . . ?
O4 C43 H43A 110.3(17) . . ?
C44 C43 H43A 111.9(18) . . ?
O4 C43 H43B 102.9(18) . . ?
C44 C43 H43B 114.7(18) . . ?
H43A C43 H43B 108(2) . . ?
C43 C44 H44A 113(3) . . ?
C43 C44 H44B 99(3) . . ?
H44A C44 H44B 105(3) . . ?
C43 C44 H44C 108(2) . . ?
H44A C44 H44C 110(3) . . ?
H44B C44 H44C 121(4) . . ?
C53 O5 C51 114.19(14) . . ?
O5 C51 C52 109.73(17) . . ?
O5 C51 H51A 109.1(15) . . ?
C52 C51 H51A 111.6(14) . . ?
O5 C51 H51B 106.8(15) . . ?
C52 C51 H51B 113.0(14) . . ?
H51A C51 H51B 106(2) . . ?
C51 C52 H52A 113.1(15) . . ?
C51 C52 H52B 108.7(17) . . ?
H52A C52 H52B 109(2) . . ?
C51 C52 H52C 111.1(16) . . ?
H52A C52 H52C 109(2) . . ?
H52B C52 H52C 106(2) . . ?
O5 C53 C54 108.82(15) . . ?
O5 C53 H53A 110.0(13) . . ?
C54 C53 H53A 113.3(13) . . ?
O5 C53 H53B 108.2(14) . . ?
C54 C53 H53B 112.0(14) . . ?
H53A C53 H53B 104.4(19) . . ?
C53 C54 H54A 110.1(15) . . ?
C53 C54 H54B 109.2(14) . . ?
H54A C54 H54B 113(2) . . ?
C53 C54 H54C 108.5(15) . . ?
H54A C54 H54C 107(2) . . ?
H54B C54 H54C 109(2) . . ?
C61 O6 C63 113.01(14) . . ?
O6 C61 C62 109.17(15) . . ?
O6 C61 H61A 107.4(15) . . ?
C62 C61 H61A 111.7(15) . . ?
O6 C61 H61B 108.8(15) . . ?
C62 C61 H61B 112.9(15) . . ?
H61A C61 H61B 107(2) . . ?
C61 C62 H62A 111.9(15) . . ?
C61 C62 H62B 109.3(13) . . ?
H62A C62 H62B 108.9(19) . . ?
C61 C62 H62C 111.4(14) . . ?
H62A C62 H62C 107.8(19) . . ?
H62B C62 H62C 107.4(19) . . ?
O6 C63 C64 109.33(16) . . ?
O6 C63 H63A 110.9(14) . . ?
C64 C63 H63A 108.7(13) . . ?
O6 C63 H63B 108.2(12) . . ?
C64 C63 H63B 109.0(12) . . ?
H63A C63 H63B 110.6(18) . . ?
C63 C64 H64A 109.4(15) . . ?
C63 C64 H64B 107.7(14) . . ?
H64A C64 H64B 111(2) . . ?
C63 C64 H64C 109.6(13) . . ?
H64A C64 H64C 106.7(19) . . ?
H64B C64 H64C 112(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 C1 C11 C16 108.77(14) . . . . ?
C31 C1 C11 C16 -20.45(18) . . . . ?
C21 C1 C11 C12 -74.16(15) . . . . ?
C31 C1 C11 C12 156.63(12) . . . . ?
C16 C11 C12 O12 -177.70(12) . . . . ?
C1 C11 C12 O12 5.05(18) . . . . ?
C16 C11 C12 C13 1.8(2) . . . . ?
C1 C11 C12 C13 -175.42(12) . . . . ?
O12 C12 C13 C14 179.36(13) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C12 C13 C14 O14 178.53(13) . . . . ?
C12 C13 C14 C15 -1.8(2) . . . . ?
O14 C14 C15 C16 -178.22(13) . . . . ?
C13 C14 C15 C16 2.1(2) . . . . ?
O14 C14 C15 Cl15 -0.83(19) . . . . ?
C13 C14 C15 Cl15 179.54(11) . . . . ?
C14 C15 C16 C11 -0.4(2) . . . . ?
Cl15 C15 C16 C11 -177.85(10) . . . . ?
C12 C11 C16 C15 -1.5(2) . . . . ?
C1 C11 C16 C15 175.55(12) . . . . ?
C11 C1 C21 C26 -38.42(17) . . . . ?
C31 C1 C21 C26 89.68(15) . . . . ?
C11 C1 C21 C22 140.53(12) . . . . ?
C31 C1 C21 C22 -91.37(14) . . . . ?
C26 C21 C22 O22 179.89(12) . . . . ?
C1 C21 C22 O22 0.89(18) . . . . ?
C26 C21 C22 C23 0.47(19) . . . . ?
C1 C21 C22 C23 -178.53(12) . . . . ?
O22 C22 C23 C24 179.73(13) . . . . ?
C21 C22 C23 C24 -0.9(2) . . . . ?
C22 C23 C24 O24 -179.79(13) . . . . ?
C22 C23 C24 C25 0.2(2) . . . . ?
O24 C24 C25 C26 -179.19(12) . . . . ?
C23 C24 C25 C26 0.8(2) . . . . ?
O24 C24 C25 Cl25 -0.29(18) . . . . ?
C23 C24 C25 Cl25 179.68(10) . . . . ?
C22 C21 C26 C25 0.56(19) . . . . ?
C1 C21 C26 C25 179.53(12) . . . . ?
C24 C25 C26 C21 -1.2(2) . . . . ?
Cl25 C25 C26 C21 179.89(10) . . . . ?
C21 C1 C31 C32 146.72(12) . . . . ?
C11 C1 C31 C32 -85.07(14) . . . . ?
C21 C1 C31 C36 -36.75(16) . . . . ?
C11 C1 C31 C36 91.47(14) . . . . ?
C36 C31 C32 C36 -0.60(17) . . . 2_556 ?
C1 C31 C32 C36 176.10(12) . . . 2_556 ?
C32 C31 C36 C32 1.29(17) . . . 2_556 ?
C1 C31 C36 C32 -175.29(12) . . . 2_556 ?
C43 O4 C41 C42 170.2(2) . . . . ?
C41 O4 C43 C44 -169.3(3) . . . . ?
C53 O5 C51 C52 -165.7(2) . . . . ?
C51 O5 C53 C54 177.66(19) . . . . ?
C63 O6 C61 C62 -176.86(19) . . . . ?
C61 O6 C63 C64 179.01(19) . . . . ?

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
O12 H12 O5 0.83(2) 1.85(2) 2.6662(16) 168(2) .
O14 H14 O4 0.82(2) 1.86(2) 2.6750(16) 172(2) .
O22 H22 O14 0.72(2) 2.08(2) 2.7864(15) 168(2) 1_565
O24 H24 O6 0.82(2) 1.97(2) 2.7855(16) 173(2) .

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_marcoc5a
_database_code_depnum_ccdc_archive 'CCDC 1497841'
_audit_update_record             
;
2016-08-05 deposited with the CCDC.
2016-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_structural     'C6H4-{CH(C6H2-2,4-(OH)2,-Cl-5)2, ca 7.5(MeOH)'
_chemical_formula_moiety         'C32 H22 Cl4 O8, ca 7.5(C H4 O)'
_chemical_formula_sum            'C39.50 H52 Cl4 O15.50'
_chemical_formula_weight         916.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.5190(3)
_cell_length_b                   12.8094(5)
_cell_length_c                   15.5844(4)
_cell_angle_alpha                79.044(3)
_cell_angle_beta                 77.462(2)
_cell_angle_gamma                71.732(3)
_cell_volume                     2112.99(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    6098
_cell_measurement_theta_min      2.9858
_cell_measurement_theta_max      32.6339

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             962
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.350
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93497
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
 CrysAlisPro, Agilent Technologies, Version 1.171.36.21 
 Empirical absorption correction using spherical harmonics,
  implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      140(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur 3/Sapphire3 CCD'
_diffrn_measurement_method       'Thin slice φ and ω scans'
_diffrn_detector_area_resol_mean 16.0050
_diffrn_reflns_number            20695
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.992
_diffrn_reflns_theta_max         22.495
_diffrn_reflns_theta_full        22.495
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5493
_reflns_number_gt                3401
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies, Version 1.171.36.21 
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies, Version 1.171.36.21 
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies, Version 1.171.36.21 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976 and Farrugia, 2012)'
_computing_publication_material  
'SHELXL-2014/7 (Sheldrick, 2014) and WINGX (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1686P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5493
_refine_ls_number_parameters     600
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1377
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.2403
_refine_ls_wR_factor_gt          0.1910
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.1432(4) 0.8803(5) 0.8487(3) 0.0324(14) Uani 1 1 d . . . . .
C2 C 0.1541(4) 0.8644(5) 0.7618(3) 0.0302(13) Uani 1 1 d . . . . .
H2 H 0.1535 0.7959 0.7505 0.036 Uiso 1 1 calc R U . . .
C3 C 0.1658(5) 0.9460(5) 0.6904(3) 0.0302(13) Uani 1 1 d . . . . .
C4 C 0.1601(5) 1.0490(5) 0.7086(4) 0.0338(14) Uani 1 1 d . . . . .
H4 H 0.1658 1.1058 0.6623 0.041 Uiso 1 1 calc R U . . .
C5 C 0.1460(5) 1.0688(5) 0.7955(4) 0.0368(14) Uani 1 1 d . . . . .
H5 H 0.1413 1.1388 0.8069 0.044 Uiso 1 1 calc R U . . .
C6 C 0.1389(5) 0.9842(5) 0.8653(4) 0.0372(15) Uani 1 1 d . . . . .
H6 H 0.1313 0.9973 0.9232 0.045 Uiso 1 1 calc R U . . .
C10 C 0.1479(5) 0.7817(5) 0.9216(3) 0.0310(13) Uani 1 1 d . . . . .
H10 H 0.1931 0.7152 0.8931 0.037 Uiso 1 1 calc R U . . .
C11 C 0.0232(5) 0.7659(5) 0.9677(3) 0.0317(14) Uani 1 1 d . . . . .
C12 C 0.0203(5) 0.6644(5) 1.0191(4) 0.0351(14) Uani 1 1 d . . . . .
C13 C -0.0907(5) 0.6455(5) 1.0618(4) 0.0411(15) Uani 1 1 d . . . . .
H13 H -0.0909 0.5776 1.0959 0.049 Uiso 1 1 calc R U . . .
C14 C -0.2026(5) 0.7270(5) 1.0544(4) 0.0378(15) Uani 1 1 d . . . . .
C15 C -0.2000(5) 0.8261(5) 1.0028(3) 0.0333(14) Uani 1 1 d . . . . .
C16 C -0.0888(5) 0.8457(5) 0.9602(3) 0.0331(14) Uani 1 1 d . . . . .
H16 H -0.0893 0.9136 0.9258 0.040 Uiso 1 1 calc R U . . .
O12 O 0.1311(3) 0.5840(4) 1.0247(3) 0.0425(11) Uani 1 1 d . . . . .
O14 O -0.3129(4) 0.7100(5) 1.0979(3) 0.0524(13) Uani 1 1 d . . . . .
Cl15 Cl -0.33940(12) 0.92825(14) 0.99188(11) 0.0493(5) Uani 1 1 d . . . . .
C21 C 0.2251(5) 0.7877(5) 0.9876(3) 0.0329(14) Uani 1 1 d . . . . .
C22 C 0.3549(5) 0.7561(5) 0.9628(3) 0.0372(15) Uani 1 1 d . . . . .
C23 C 0.4308(5) 0.7666(5) 1.0173(4) 0.0370(15) Uani 1 1 d . . . . .
H23 H 0.5164 0.7464 0.9997 0.044 Uiso 1 1 calc R U . . .
C24 C 0.3791(5) 0.8068(5) 1.0972(4) 0.0374(15) Uani 1 1 d . . . . .
C25 C 0.2519(5) 0.8355(5) 1.1233(3) 0.0308(13) Uani 1 1 d . . . . .
C26 C 0.1776(5) 0.8252(5) 1.0684(4) 0.0348(14) Uani 1 1 d . . . . .
H26 H 0.0921 0.8443 1.0870 0.042 Uiso 1 1 calc R U . . .
O22 O 0.4024(4) 0.7181(4) 0.8822(3) 0.0491(13) Uani 1 1 d . . . . .
O24 O 0.4514(5) 0.8216(6) 1.1500(4) 0.0436(14) Uani 1 1 d . . . . .
Cl25 Cl 0.18612(13) 0.88874(14) 1.22280(9) 0.0428(5) Uani 1 1 d . . . . .
C30 C 0.1956(5) 0.9215(5) 0.5954(3) 0.0277(12) Uani 1 1 d . . . . .
H30 H 0.1660 0.9919 0.5582 0.033 Uiso 1 1 calc R U . . .
C31 C 0.1282(5) 0.8414(5) 0.5798(3) 0.0263(13) Uani 1 1 d . . . . .
C32 C -0.0011(5) 0.8793(4) 0.5840(3) 0.0253(12) Uani 1 1 d . . . . .
C33 C -0.0645(5) 0.8096(5) 0.5689(3) 0.0310(13) Uani 1 1 d . . . . .
H33 H -0.1497 0.8358 0.5697 0.037 Uiso 1 1 calc R U . . .
C34 C -0.0016(5) 0.7013(5) 0.5528(4) 0.0337(14) Uani 1 1 d . . . . .
C35 C 0.1268(5) 0.6640(5) 0.5494(4) 0.0373(14) Uani 1 1 d . . . . .
C36 C 0.1887(5) 0.7344(5) 0.5639(3) 0.0289(13) Uani 1 1 d . . . . .
H36 H 0.2739 0.7082 0.5629 0.035 Uiso 1 1 calc R U . . .
O32 O -0.0595(3) 0.9849(3) 0.6010(2) 0.0311(9) Uani 1 1 d . . . . .
O34 O -0.0611(4) 0.6314(4) 0.5381(3) 0.0443(12) Uani 1 1 d . . . . .
Cl35 Cl 0.20689(13) 0.53049(14) 0.52721(12) 0.0525(5) Uani 1 1 d . . . . .
C41 C 0.3353(5) 0.8798(5) 0.5658(3) 0.0283(13) Uani 1 1 d . . . . .
C42 C 0.3885(5) 0.9024(5) 0.4758(3) 0.0296(13) Uani 1 1 d . . . . .
C43 C 0.5149(5) 0.8610(5) 0.4467(4) 0.0335(14) Uani 1 1 d . . . . .
H43 H 0.5477 0.8769 0.3874 0.040 Uiso 1 1 calc R U . . .
C44 C 0.5927(4) 0.7964(5) 0.5049(4) 0.0321(14) Uani 1 1 d . . . . .
C45 C 0.5421(5) 0.7753(5) 0.5919(4) 0.0363(14) Uani 1 1 d . . . . .
C46 C 0.4162(5) 0.8170(5) 0.6211(3) 0.0339(14) Uani 1 1 d . . . . .
H46 H 0.3851 0.8016 0.6809 0.041 Uiso 1 1 calc R U . . .
O42 O 0.3100(3) 0.9644(3) 0.4176(3) 0.0348(10) Uani 1 1 d . . . . .
O44 O 0.7179(3) 0.7529(4) 0.4773(3) 0.0410(10) Uani 1 1 d . . . . .
H44 H 0.7291 0.7264 0.4312 0.09(3) Uiso 1 1 calc R . . . .
Cl45 Cl 0.63812(14) 0.69228(16) 0.66696(10) 0.0557(5) Uani 1 1 d . . . . .
O51 O 0.1194(4) 0.4377(4) 1.1787(3) 0.0458(11) Uani 1 1 d . . . . .
C52 C 0.0871(8) 0.3371(7) 1.1972(5) 0.075(2) Uani 1 1 d . . . . .
H52A H 0.1438 0.2829 1.2316 0.113 Uiso 1 1 calc R U . . .
H52B H 0.0914 0.3108 1.1425 0.113 Uiso 1 1 calc R U . . .
H52C H 0.0043 0.3492 1.2300 0.113 Uiso 1 1 calc R U . . .
O53 O 0.0250(5) 0.5554(5) 1.3197(4) 0.0554(13) Uani 1 1 d . . . . .
C54 C 0.0831(8) 0.6406(7) 1.3102(5) 0.070(2) Uani 1 1 d . . . . .
H54A H 0.0454 0.6854 1.3573 0.106 Uiso 1 1 calc R U . . .
H54B H 0.0734 0.6861 1.2542 0.106 Uiso 1 1 calc R U . . .
H54C H 0.1698 0.6081 1.3126 0.106 Uiso 1 1 calc R U . . .
O55 O -0.2974(6) 0.5037(6) 1.1369(5) 0.0615(19) Uani 0.7 1 d . . P A 1
H55 H -0.2999 0.4659 1.1007 0.02(2) Uiso 0.7 1 calc R . P A 1
C56 C -0.3120(11) 0.4479(9) 1.2190(8) 0.071(3) Uani 0.7 1 d . . P A 1
H56A H -0.2422 0.4403 1.2463 0.107 Uiso 0.7 1 calc R U P A 1
H56B H -0.3177 0.3757 1.2154 0.107 Uiso 0.7 1 calc R U P A 1
H56C H -0.3865 0.4879 1.2538 0.107 Uiso 0.7 1 calc R U P A 1
O57 O 0.5314(6) 0.6794(7) 1.3044(4) 0.067(2) Uani 0.7 1 d . . P B 1
C58 C 0.4566(13) 0.6301(16) 1.3789(9) 0.095(5) Uani 0.7 1 d . . P B 1
H58A H 0.4925 0.5511 1.3872 0.143 Uiso 0.7 1 calc R U P B 1
H58B H 0.3739 0.6468 1.3671 0.143 Uiso 0.7 1 calc R U P B 1
H58C H 0.4542 0.6598 1.4316 0.143 Uiso 0.7 1 calc R U P B 1
O59 O 0.4180(5) 0.9943(6) 0.2533(3) 0.0706(17) Uani 1 1 d . . . . .
C60 C 0.5033(8) 1.0483(9) 0.2106(5) 0.082(3) Uani 1 1 d . . . . .
H60A H 0.4640 1.1268 0.2037 0.123 Uiso 1 1 calc R U . . .
H60B H 0.5375 1.0245 0.1533 0.123 Uiso 1 1 calc R U . . .
H60C H 0.5684 1.0317 0.2448 0.123 Uiso 1 1 calc R U . . .
O61 O 0.7715(6) 0.7004(5) 0.3137(3) 0.0698(15) Uani 1 1 d . . . . .
O63 O 0.6295(4) 0.5828(4) 0.8851(3) 0.0560(13) Uani 1 1 d . . . . .
C64 C 0.6177(7) 0.4817(7) 0.8747(7) 0.083(3) Uani 1 1 d . . . . .
H64A H 0.6835 0.4227 0.8970 0.125 Uiso 1 1 calc R U . . .
H64B H 0.6222 0.4787 0.8129 0.125 Uiso 1 1 calc R U . . .
H64C H 0.5393 0.4736 0.9069 0.125 Uiso 1 1 calc R U . . .
O65 O 0.673(3) 0.571(3) 0.240(2) 0.100(10) Uiso 0.2 1 d . . P C 2
C66 C 0.613(3) 0.475(3) 0.2948(19) 0.109(9) Uiso 0.4 1 d . . P C 2
O67 O 0.494(3) 0.454(3) 0.418(2) 0.087(8) Uiso 0.2 1 d . . P D 2
C68 C 0.515(7) 0.576(8) 0.439(6) 0.15(3) Uiso 0.2 1 d . . P D 2
O69 O 0.4040(13) 0.6729(12) 0.3517(9) 0.079(4) Uiso 0.5 1 d . . P E 2
H12 H 0.113(7) 0.535(6) 1.089(5) 0.08(2) Uiso 1 1 d . . . . .
H14 H -0.300(5) 0.644(5) 1.102(4) 0.028(18) Uiso 1 1 d . . . . .
H22 H 0.476(6) 0.695(6) 0.883(4) 0.05(2) Uiso 1 1 d . . . . .
H24 H 0.531(6) 0.803(5) 1.109(4) 0.032(16) Uiso 0.9 1 d . . P . .
H24A H 0.458(10) 0.787(9) 1.180(7) 0.03(4) Uiso 0.7 1 d . . P . .
H32 H -0.137(7) 1.014(6) 0.585(4) 0.06(2) Uiso 1 1 d . . . . .
H34 H -0.124(7) 0.668(6) 0.539(5) 0.06(3) Uiso 1 1 d . . . . .
H42 H 0.338(7) 0.965(6) 0.366(5) 0.06(2) Uiso 1 1 d . . . . .
H51 H 0.094(5) 0.466(5) 1.223(4) 0.031(18) Uiso 1 1 d . . . . .
H53 H 0.034(5) 0.510(5) 1.361(4) 0.023(17) Uiso 1 1 d . . . . .
H59 H 0.407(6) 0.949(6) 0.230(4) 0.05(2) Uiso 1 1 d . . . . .
H61A H 0.717(6) 0.654(6) 0.296(4) 0.057(19) Uiso 1 1 d . . . . .
H61B H 0.843(8) 0.637(7) 0.297(5) 0.09(3) Uiso 1 1 d . . . . .
H63 H 0.710(5) 0.589(4) 0.857(3) 0.028(14) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.381(7) . ?
C1 C6 1.388(8) . ?
C1 C10 1.524(8) . ?
C2 C3 1.389(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(8) . ?
C3 C30 1.515(7) . ?
C4 C5 1.390(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C10 C11 1.516(7) . ?
C10 C21 1.525(7) . ?
C10 H10 0.9800 . ?
C11 C16 1.384(8) . ?
C11 C12 1.397(8) . ?
C12 O12 1.374(7) . ?
C12 C13 1.378(8) . ?
C13 C14 1.393(8) . ?
C13 H13 0.9300 . ?
C14 O14 1.366(7) . ?
C14 C15 1.372(8) . ?
C15 C16 1.383(8) . ?
C15 Cl15 1.743(6) . ?
C16 H16 0.9300 . ?
O12 H12 1.10(8) . ?
O14 H14 0.81(6) . ?
C21 C26 1.371(8) . ?
C21 C22 1.407(7) . ?
C22 O22 1.371(6) . ?
C22 C23 1.394(8) . ?
C23 C24 1.379(8) . ?
C23 H23 0.9300 . ?
C24 O24 1.364(8) . ?
C24 C25 1.381(8) . ?
C25 C26 1.384(7) . ?
C25 Cl25 1.736(5) . ?
C26 H26 0.9300 . ?
O22 H22 0.80(7) . ?
O24 H24 0.98(7) . ?
O24 H24A 0.58(9) . ?
C30 C41 1.524(7) . ?
C30 C31 1.546(7) . ?
C30 H30 0.9800 . ?
C31 C36 1.372(8) . ?
C31 C32 1.405(7) . ?
C32 O32 1.357(6) . ?
C32 C33 1.396(8) . ?
C33 C34 1.392(8) . ?
C33 H33 0.9300 . ?
C34 O34 1.362(7) . ?
C34 C35 1.397(8) . ?
C35 C36 1.387(8) . ?
C35 Cl35 1.730(6) . ?
C36 H36 0.9300 . ?
O32 H32 0.92(7) . ?
O34 H34 0.73(7) . ?
C41 C46 1.369(8) . ?
C41 C42 1.417(7) . ?
C42 O42 1.380(6) . ?
C42 C43 1.388(7) . ?
C43 C44 1.384(8) . ?
C43 H43 0.9300 . ?
C44 C45 1.366(8) . ?
C44 O44 1.376(6) . ?
C45 C46 1.384(8) . ?
C45 Cl45 1.753(6) . ?
C46 H46 0.9300 . ?
O42 H42 0.79(8) . ?
O44 H44 0.8200 . ?
O51 C52 1.412(9) . ?
O51 H51 0.80(6) . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
O53 C54 1.420(9) . ?
O53 H53 0.78(6) . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
O55 C56 1.345(13) . ?
O55 H55 0.8200 . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
O57 C58 1.455(14) . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
O59 C60 1.362(9) . ?
O59 H59 0.79(7) . ?
C60 H60A 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60C 0.9600 . ?
O61 H61A 1.10(7) . ?
O61 H61B 0.99(9) . ?
O63 C64 1.386(10) . ?
O63 H63 0.95(6) . ?
C64 H64A 0.9600 . ?
C64 H64B 0.9600 . ?
C64 H64C 0.9600 . ?
O65 C66 1.61(4) . ?
O67 C68 1.75(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.1(5) . . ?
C2 C1 C10 119.4(5) . . ?
C6 C1 C10 122.4(5) . . ?
C1 C2 C3 123.1(5) . . ?
C1 C2 H2 118.4 . . ?
C3 C2 H2 118.4 . . ?
C4 C3 C2 117.6(5) . . ?
C4 C3 C30 120.3(5) . . ?
C2 C3 C30 121.8(5) . . ?
C3 C4 C5 120.8(5) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 120.2(6) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 120.2(5) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C11 C10 C1 115.6(4) . . ?
C11 C10 C21 111.7(4) . . ?
C1 C10 C21 109.3(5) . . ?
C11 C10 H10 106.6 . . ?
C1 C10 H10 106.6 . . ?
C21 C10 H10 106.6 . . ?
C16 C11 C12 117.9(5) . . ?
C16 C11 C10 123.6(5) . . ?
C12 C11 C10 118.5(5) . . ?
O12 C12 C13 121.2(5) . . ?
O12 C12 C11 118.0(5) . . ?
C13 C12 C11 120.8(5) . . ?
C12 C13 C14 120.7(6) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
O14 C14 C15 120.3(5) . . ?
O14 C14 C13 121.2(6) . . ?
C15 C14 C13 118.5(5) . . ?
C14 C15 C16 121.0(5) . . ?
C14 C15 Cl15 119.0(4) . . ?
C16 C15 Cl15 120.0(5) . . ?
C15 C16 C11 121.1(6) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C12 O12 H12 104(4) . . ?
C14 O14 H14 103(4) . . ?
C26 C21 C22 117.2(5) . . ?
C26 C21 C10 125.0(5) . . ?
C22 C21 C10 117.7(5) . . ?
O22 C22 C23 122.0(5) . . ?
O22 C22 C21 117.2(5) . . ?
C23 C22 C21 120.7(5) . . ?
C24 C23 C22 120.2(5) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
O24 C24 C23 121.0(5) . . ?
O24 C24 C25 119.3(5) . . ?
C23 C24 C25 119.6(5) . . ?
C24 C25 C26 119.7(5) . . ?
C24 C25 Cl25 119.8(4) . . ?
C26 C25 Cl25 120.4(4) . . ?
C21 C26 C25 122.5(5) . . ?
C21 C26 H26 118.7 . . ?
C25 C26 H26 118.7 . . ?
C22 O22 H22 103(5) . . ?
C24 O24 H24 97(3) . . ?
C24 O24 H24A 112(10) . . ?
H24 O24 H24A 104(10) . . ?
C3 C30 C41 110.6(4) . . ?
C3 C30 C31 113.0(4) . . ?
C41 C30 C31 111.7(4) . . ?
C3 C30 H30 107.1 . . ?
C41 C30 H30 107.1 . . ?
C31 C30 H30 107.1 . . ?
C36 C31 C32 118.6(5) . . ?
C36 C31 C30 122.9(5) . . ?
C32 C31 C30 118.5(5) . . ?
O32 C32 C33 122.3(5) . . ?
O32 C32 C31 117.8(5) . . ?
C33 C32 C31 119.9(5) . . ?
C34 C33 C32 120.6(5) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
O34 C34 C33 121.9(5) . . ?
O34 C34 C35 119.0(5) . . ?
C33 C34 C35 119.0(5) . . ?
C36 C35 C34 119.7(5) . . ?
C36 C35 Cl35 120.7(4) . . ?
C34 C35 Cl35 119.6(4) . . ?
C31 C36 C35 122.0(5) . . ?
C31 C36 H36 119.0 . . ?
C35 C36 H36 119.0 . . ?
C32 O32 H32 115(4) . . ?
C34 O34 H34 101(6) . . ?
C46 C41 C42 115.9(5) . . ?
C46 C41 C30 123.8(5) . . ?
C42 C41 C30 120.2(5) . . ?
O42 C42 C43 121.1(5) . . ?
O42 C42 C41 117.8(4) . . ?
C43 C42 C41 121.1(5) . . ?
C44 C43 C42 120.8(5) . . ?
C44 C43 H43 119.6 . . ?
C42 C43 H43 119.6 . . ?
C45 C44 O44 119.9(5) . . ?
C45 C44 C43 118.3(5) . . ?
O44 C44 C43 121.8(5) . . ?
C44 C45 C46 121.0(5) . . ?
C44 C45 Cl45 119.3(4) . . ?
C46 C45 Cl45 119.7(4) . . ?
C41 C46 C45 122.9(5) . . ?
C41 C46 H46 118.6 . . ?
C45 C46 H46 118.6 . . ?
C42 O42 H42 117(5) . . ?
C44 O44 H44 109.5 . . ?
C52 O51 H51 106(4) . . ?
O51 C52 H52A 109.5 . . ?
O51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
O51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C54 O53 H53 116(4) . . ?
O53 C54 H54A 109.5 . . ?
O53 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
O53 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C56 O55 H55 109.5 . . ?
O55 C56 H56A 109.5 . . ?
O55 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
O55 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
O57 C58 H58A 109.5 . . ?
O57 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
O57 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C60 O59 H59 118(5) . . ?
O59 C60 H60A 109.5 . . ?
O59 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
O59 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
H61A O61 H61B 85(6) . . ?
C64 O63 H63 110(3) . . ?
O63 C64 H64A 109.5 . . ?
O63 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
O63 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 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 2.7(8) . . . . ?
C10 C1 C2 C3 -172.0(5) . . . . ?
C1 C2 C3 C4 -3.3(7) . . . . ?
C1 C2 C3 C30 171.3(5) . . . . ?
C2 C3 C4 C5 1.5(7) . . . . ?
C30 C3 C4 C5 -173.1(5) . . . . ?
C3 C4 C5 C6 0.8(8) . . . . ?
C2 C1 C6 C5 -0.3(8) . . . . ?
C10 C1 C6 C5 174.2(5) . . . . ?
C4 C5 C6 C1 -1.4(8) . . . . ?
C2 C1 C10 C11 -94.2(6) . . . . ?
C6 C1 C10 C11 91.4(6) . . . . ?
C2 C1 C10 C21 138.8(5) . . . . ?
C6 C1 C10 C21 -35.6(6) . . . . ?
C1 C10 C11 C16 -13.6(7) . . . . ?
C21 C10 C11 C16 112.2(6) . . . . ?
C1 C10 C11 C12 164.7(5) . . . . ?
C21 C10 C11 C12 -69.4(7) . . . . ?
C16 C11 C12 O12 178.3(5) . . . . ?
C10 C11 C12 O12 -0.2(8) . . . . ?
C16 C11 C12 C13 -1.0(8) . . . . ?
C10 C11 C12 C13 -179.5(5) . . . . ?
O12 C12 C13 C14 -179.0(5) . . . . ?
C11 C12 C13 C14 0.3(9) . . . . ?
C12 C13 C14 O14 -178.6(6) . . . . ?
C12 C13 C14 C15 0.8(9) . . . . ?
O14 C14 C15 C16 178.3(5) . . . . ?
C13 C14 C15 C16 -1.1(9) . . . . ?
O14 C14 C15 Cl15 -1.4(8) . . . . ?
C13 C14 C15 Cl15 179.2(4) . . . . ?
C14 C15 C16 C11 0.3(8) . . . . ?
Cl15 C15 C16 C11 -180.0(4) . . . . ?
C12 C11 C16 C15 0.7(8) . . . . ?
C10 C11 C16 C15 179.1(5) . . . . ?
C11 C10 C21 C26 -28.4(8) . . . . ?
C1 C10 C21 C26 100.8(6) . . . . ?
C11 C10 C21 C22 153.9(5) . . . . ?
C1 C10 C21 C22 -76.9(7) . . . . ?
C26 C21 C22 O22 179.7(5) . . . . ?
C10 C21 C22 O22 -2.5(9) . . . . ?
C26 C21 C22 C23 -2.2(9) . . . . ?
C10 C21 C22 C23 175.7(6) . . . . ?
O22 C22 C23 C24 179.0(6) . . . . ?
C21 C22 C23 C24 0.9(10) . . . . ?
C22 C23 C24 O24 -177.5(6) . . . . ?
C22 C23 C24 C25 0.6(9) . . . . ?
O24 C24 C25 C26 177.3(6) . . . . ?
C23 C24 C25 C26 -0.9(9) . . . . ?
O24 C24 C25 Cl25 -0.6(8) . . . . ?
C23 C24 C25 Cl25 -178.7(5) . . . . ?
C22 C21 C26 C25 2.0(9) . . . . ?
C10 C21 C26 C25 -175.7(6) . . . . ?
C24 C25 C26 C21 -0.5(9) . . . . ?
Cl25 C25 C26 C21 177.4(5) . . . . ?
C4 C3 C30 C41 87.6(6) . . . . ?
C2 C3 C30 C41 -86.8(6) . . . . ?
C4 C3 C30 C31 -146.3(5) . . . . ?
C2 C3 C30 C31 39.3(7) . . . . ?
C3 C30 C31 C36 -109.5(5) . . . . ?
C41 C30 C31 C36 16.0(7) . . . . ?
C3 C30 C31 C32 69.1(6) . . . . ?
C41 C30 C31 C32 -165.4(4) . . . . ?
C36 C31 C32 O32 179.1(4) . . . . ?
C30 C31 C32 O32 0.4(7) . . . . ?
C36 C31 C32 C33 -2.2(7) . . . . ?
C30 C31 C32 C33 179.0(4) . . . . ?
O32 C32 C33 C34 -179.2(5) . . . . ?
C31 C32 C33 C34 2.2(7) . . . . ?
C32 C33 C34 O34 179.8(5) . . . . ?
C32 C33 C34 C35 -1.7(8) . . . . ?
O34 C34 C35 C36 179.8(5) . . . . ?
C33 C34 C35 C36 1.3(8) . . . . ?
O34 C34 C35 Cl35 -0.2(8) . . . . ?
C33 C34 C35 Cl35 -178.7(4) . . . . ?
C32 C31 C36 C35 1.9(8) . . . . ?
C30 C31 C36 C35 -179.5(5) . . . . ?
C34 C35 C36 C31 -1.4(8) . . . . ?
Cl35 C35 C36 C31 178.6(4) . . . . ?
C3 C30 C41 C46 33.3(8) . . . . ?
C31 C30 C41 C46 -93.5(6) . . . . ?
C3 C30 C41 C42 -148.8(5) . . . . ?
C31 C30 C41 C42 84.4(6) . . . . ?
C46 C41 C42 O42 179.3(5) . . . . ?
C30 C41 C42 O42 1.2(8) . . . . ?
C46 C41 C42 C43 0.9(8) . . . . ?
C30 C41 C42 C43 -177.1(5) . . . . ?
O42 C42 C43 C44 -178.3(5) . . . . ?
C41 C42 C43 C44 0.0(9) . . . . ?
C42 C43 C44 C45 -0.6(9) . . . . ?
C42 C43 C44 O44 178.8(5) . . . . ?
O44 C44 C45 C46 -179.1(5) . . . . ?
C43 C44 C45 C46 0.3(9) . . . . ?
O44 C44 C45 Cl45 -0.2(8) . . . . ?
C43 C44 C45 Cl45 179.2(4) . . . . ?
C42 C41 C46 C45 -1.3(9) . . . . ?
C30 C41 C46 C45 176.7(5) . . . . ?
C44 C45 C46 C41 0.7(10) . . . . ?
Cl45 C45 C46 C41 -178.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O12 H12 O51 1.10(8) 1.68(8) 2.756(6) 166(6) .
O14 H14 O55 0.81(6) 1.76(7) 2.555(9) 165(6) .
O14 H14 O65 0.81(6) 2.17(7) 2.57(4) 111(5) 1_456
O22 H22 O63 0.80(7) 1.90(7) 2.651(6) 155(7) .
O24 H24 O14 0.98(7) 1.81(7) 2.669(7) 144(5) 1_655
O24 H24 Cl15 0.98(7) 2.72(7) 3.457(7) 133(5) 1_655
O24 H24A O57 0.58(9) 2.31(10) 2.864(10) 160(14) .
O32 H32 O42 0.92(7) 1.93(7) 2.819(5) 161(6) 2_576
O34 H34 O44 0.73(7) 2.13(7) 2.793(6) 152(7) 1_455
O42 H42 O59 0.79(8) 1.83(8) 2.607(6) 165(8) .
O44 H44 O61 0.82 1.86 2.654(6) 164.0 .
O51 H51 O53 0.80(6) 1.94(6) 2.734(7) 171(6) .
O53 H53 O34 0.78(6) 2.15(6) 2.927(8) 171(6) 2_567
O55 H55 O12 0.82 2.46 2.984(8) 122.7 2_567
O59 H59 O24 0.79(7) 2.11(7) 2.860(8) 158(7) 1_554
O59 H59 Cl25 0.79(7) 2.91(7) 3.499(5) 132(6) 1_554
O61 H61A O65 1.10(7) 1.74(8) 2.80(3) 161(5) .
O61 H61A O57 1.10(7) 2.03(7) 2.898(9) 133(5) 1_554
O61 H61B O53 0.99(9) 2.10(9) 2.939(8) 142(7) 1_654
O63 H63 O51 0.95(6) 1.87(6) 2.793(6) 164(5) 2_667

_refine_diff_density_max         1.106
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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_marcoc4a
_database_code_depnum_ccdc_archive 'CCDC 1497842'
_audit_update_record             
;
2016-08-05 deposited with the CCDC.
2016-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_structural     
'o-C6H4-{CH(C6H2-2,4-(OH)2,-5-Cl)2, ca 2(MeOH), ca 5(Et2O)'
_chemical_formula_moiety         'C32 H22 Cl4 O8, ca 2(C H4 O), ca 5(C4 H10 O)'
_chemical_formula_sum            'C54 H80 Cl4 O15'
_chemical_formula_weight         1111.0

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.6713(5)
_cell_length_b                   13.6859(4)
_cell_length_c                   15.8507(5)
_cell_angle_alpha                87.748(3)
_cell_angle_beta                 71.565(3)
_cell_angle_gamma                84.007(3)
_cell_volume                     2798.10(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    5728
_cell_measurement_theta_min      2.9727
_cell_measurement_theta_max      32.5175

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.277
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro RED, Oxford Diffraction Ltd., Version 1.171.33.55 
 Empirical absorption correction using spherical harmonics,
  implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      140(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur 3/Sapphire3 CCD'
_diffrn_measurement_method       'Thin slice φ and ω scans'
_diffrn_detector_area_resol_mean 16.0050
_diffrn_reflns_number            30403
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.087
_diffrn_reflns_theta_max         22.500
_diffrn_reflns_theta_full        22.500
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7299
_reflns_number_gt                5321
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
 CrysAlisPro CCD, Oxford Diffraction Ltd., Version 1.171.35.11 
;
_computing_cell_refinement       
;
 CrysAlisPro RED, Oxford Diffraction Ltd., Version 1.171.35.11 
;
_computing_data_reduction        
;
 CrysAlisPro RED, Oxford Diffraction Ltd., Version 1.171.35.11
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976 and Farrugia, 2012)'
_computing_publication_material  
'SHELXL-2014/7 (Sheldrick, 2014) and WINGX (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0689P)²+3.0458P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7299
_refine_ls_number_parameters     768
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.1718
_refine_ls_wR_factor_gt          0.1565
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.6232(3) 0.1684(3) 0.7637(2) 0.0281(9) Uani 1 1 d . . . . .
C2 C 0.5306(3) 0.1383(3) 0.8238(2) 0.0282(9) Uani 1 1 d . . . . .
C3 C 0.5375(3) 0.0599(3) 0.8804(2) 0.0343(10) Uani 1 1 d . . . . .
H3 H 0.4770 0.0394 0.9203 0.041 Uiso 1 1 calc R U . . .
C4 C 0.6315(3) 0.0117(3) 0.8790(2) 0.0429(11) Uani 1 1 d . . . . .
H4 H 0.6341 -0.0408 0.9176 0.051 Uiso 1 1 calc R U . . .
C5 C 0.7218(3) 0.0411(3) 0.8205(3) 0.0431(11) Uani 1 1 d . . . . .
H5 H 0.7855 0.0090 0.8195 0.052 Uiso 1 1 calc R U . . .
C6 C 0.7167(3) 0.1189(3) 0.7633(2) 0.0356(10) Uani 1 1 d . . . . .
H6 H 0.7777 0.1385 0.7235 0.043 Uiso 1 1 calc R U . . .
C10 C 0.6191(3) 0.2564(3) 0.7024(2) 0.0268(9) Uani 1 1 d . . . . .
H10 H 0.5564 0.2541 0.6855 0.032 Uiso 1 1 calc R U . . .
C11 C 0.7094(3) 0.2516(3) 0.6162(2) 0.0258(9) Uani 1 1 d . . . . .
C12 C 0.7148(3) 0.1820(3) 0.5517(2) 0.0291(9) Uani 1 1 d . . . . .
C13 C 0.7916(3) 0.1793(3) 0.4701(2) 0.0315(10) Uani 1 1 d . . . . .
H13 H 0.7936 0.1326 0.4283 0.038 Uiso 1 1 calc R U . . .
C14 C 0.8647(3) 0.2454(3) 0.4505(2) 0.0379(11) Uani 1 1 d . . . . .
C15 C 0.8627(3) 0.3122(3) 0.5140(3) 0.0439(12) Uani 1 1 d . . . . .
C16 C 0.7851(3) 0.3158(3) 0.5950(2) 0.0368(11) Uani 1 1 d . . . . .
H16 H 0.7839 0.3627 0.6363 0.044 Uiso 1 1 calc R U . . .
O12 O 0.6398(2) 0.1191(2) 0.57340(17) 0.0386(7) Uani 1 1 d . . . . .
O14 O 0.9403(2) 0.2470(2) 0.36880(18) 0.0532(9) Uani 1 1 d . . . . .
Cl15 Cl 0.95770(11) 0.39398(11) 0.49090(8) 0.0852(6) Uani 1 1 d . . . . .
C21 C 0.6054(3) 0.3524(3) 0.7517(2) 0.0284(9) Uani 1 1 d . . . . .
C22 C 0.5510(3) 0.4344(3) 0.7289(3) 0.0438(11) Uani 1 1 d . . . . .
C23 C 0.5350(4) 0.5225(3) 0.7746(3) 0.0541(13) Uani 1 1 d . . . . .
H23 H 0.4980 0.5768 0.7582 0.065 Uiso 1 1 calc R U . . .
C24 C 0.5736(3) 0.5293(3) 0.8438(3) 0.0471(12) Uani 1 1 d . . . . .
C25 C 0.6301(4) 0.4499(3) 0.8654(2) 0.0442(12) Uani 1 1 d . . . . .
C26 C 0.6447(3) 0.3623(3) 0.8204(2) 0.0390(11) Uani 1 1 d . . . . .
H26 H 0.6822 0.3086 0.8371 0.047 Uiso 1 1 calc R U . . .
O22 O 0.5145(3) 0.4264(3) 0.6588(3) 0.0735(12) Uani 1 1 d . . . . .
O24 O 0.5599(3) 0.6148(3) 0.8908(3) 0.0673(12) Uani 1 1 d . . . . .
Cl25 Cl 0.68223(14) 0.45797(10) 0.95221(8) 0.0839(5) Uani 1 1 d . . . . .
C30 C 0.4257(3) 0.1873(3) 0.8231(2) 0.0283(9) Uani 1 1 d . . . . .
H30 H 0.4350 0.2566 0.8081 0.034 Uiso 1 1 calc R U . . .
C31 C 0.3428(3) 0.1856(3) 0.9134(2) 0.0287(9) Uani 1 1 d . . . . .
C32 C 0.3452(3) 0.2498(3) 0.9791(2) 0.0330(10) Uani 1 1 d . . . . .
C33 C 0.2709(3) 0.2525(3) 1.0620(2) 0.0379(11) Uani 1 1 d . . . . .
H33 H 0.2740 0.2954 1.1049 0.045 Uiso 1 1 calc R U . . .
C34 C 0.1919(3) 0.1918(3) 1.0811(2) 0.0370(10) Uani 1 1 d . . . . .
C35 C 0.1887(3) 0.1280(3) 1.0172(3) 0.0381(11) Uani 1 1 d . . . . .
C36 C 0.2641(3) 0.1254(3) 0.9343(2) 0.0348(10) Uani 1 1 d . . . . .
H36 H 0.2612 0.0816 0.8919 0.042 Uiso 1 1 calc R U . . .
O32 O 0.4233(2) 0.3090(2) 0.95681(19) 0.0498(9) Uani 1 1 d . . . . .
O34 O 0.1160(2) 0.1927(3) 1.16255(19) 0.0517(9) Uani 1 1 d . . . . .
Cl35 Cl 0.08874(9) 0.05187(10) 1.03959(7) 0.0623(4) Uani 1 1 d . . . . .
C41 C 0.3912(3) 0.1460(3) 0.7498(2) 0.0277(9) Uani 1 1 d . . . . .
C42 C 0.3155(3) 0.1977(3) 0.7213(3) 0.0412(11) Uani 1 1 d . . . . .
C43 C 0.2806(3) 0.1603(3) 0.6560(3) 0.0448(11) Uani 1 1 d . . . . .
H43 H 0.2287 0.1962 0.6384 0.054 Uiso 1 1 calc R U . . .
C44 C 0.3231(3) 0.0710(3) 0.6180(3) 0.0361(10) Uani 1 1 d . . . . .
C45 C 0.3982(3) 0.0188(3) 0.6461(3) 0.0380(11) Uani 1 1 d . . . . .
C46 C 0.4328(3) 0.0563(3) 0.7110(2) 0.0327(10) Uani 1 1 d . . . . .
H46 H 0.4848 0.0202 0.7284 0.039 Uiso 1 1 calc R U . . .
O42 O 0.2721(3) 0.2868(2) 0.7600(2) 0.0663(10) Uani 1 1 d . . . . .
O44 O 0.2912(3) 0.0299(3) 0.5556(2) 0.0551(10) Uani 1 1 d . . . . .
Cl45 Cl 0.45384(11) -0.09376(10) 0.59792(10) 0.0769(5) Uani 1 1 d . . . . .
O51 O 0.9258(3) 0.1265(4) 0.2494(2) 0.1059(19) Uani 1 1 d . . . . .
C52 C 0.8452(5) 0.1062(7) 0.2166(4) 0.133(3) Uani 1 1 d . . . . .
H52A H 0.7795 0.1245 0.2603 0.199 Uiso 1 1 calc R U . . .
H52B H 0.8513 0.0373 0.2045 0.199 Uiso 1 1 calc R U . . .
H52C H 0.8502 0.1431 0.1629 0.199 Uiso 1 1 calc R U . . .
O61 O 1.1090(3) 0.3391(3) 0.2704(2) 0.0850(15) Uani 1 1 d . . . . .
C62 C 1.1735(4) 0.4025(4) 0.2866(4) 0.090(2) Uani 1 1 d . . . . .
H62A H 1.1328 0.4599 0.3163 0.135 Uiso 1 1 calc R U . . .
H62B H 1.2216 0.4214 0.2312 0.135 Uiso 1 1 calc R U . . .
H62C H 1.2110 0.3701 0.3235 0.135 Uiso 1 1 calc R U . . .
C71 C 0.0122(10) 0.0900(14) 0.6930(11) 0.123(6) Uani 0.5 1 d . . P A 1
H71A H -0.0552 0.0751 0.7300 0.184 Uiso 0.5 1 calc R U P A 1
H71B H 0.0637 0.0411 0.7021 0.184 Uiso 0.5 1 calc R U P A 1
H71C H 0.0254 0.1534 0.7083 0.184 Uiso 0.5 1 calc R U P A 1
C72 C 0.0157(17) 0.0903(19) 0.6110(16) 0.109(8) Uani 0.5 1 d . . P A 1
H72A H -0.0396 0.1379 0.6052 0.130 Uiso 0.5 1 calc R U P A 1
H72B H -0.0015 0.0264 0.5991 0.130 Uiso 0.5 1 calc R U P A 1
O73 O 0.1075(10) 0.1104(6) 0.5414(7) 0.090(2) Uani 0.6 1 d . . P A 1
C74 C 0.102(3) 0.089(3) 0.468(2) 0.143(12) Uiso 0.35 1 d . . P A 1
H74A H 0.0413 0.1261 0.4585 0.172 Uiso 0.35 1 calc R U P A 1
H74B H 0.0923 0.0198 0.4674 0.172 Uiso 0.35 1 calc R U P A 1
C75 C 0.2031(8) 0.1118(7) 0.3871(6) 0.127(3) Uani 0.4 1 d . . P A 1
H75A H 0.1951 0.0942 0.3318 0.190 Uiso 0.4 1 calc R U P A 1
H75B H 0.2119 0.1806 0.3863 0.190 Uiso 0.4 1 calc R U P A 1
H75C H 0.2628 0.0742 0.3953 0.190 Uiso 0.4 1 calc R U P A 1
C76 C 0.2983(14) 0.1485(13) 0.3448(10) 0.139(6) Uani 0.55 1 d . . P B 2
H76A H 0.3216 0.1304 0.2832 0.208 Uiso 0.55 1 calc R U P B 2
H76B H 0.2905 0.2187 0.3495 0.208 Uiso 0.55 1 calc R U P B 2
H76C H 0.3483 0.1214 0.3725 0.208 Uiso 0.55 1 calc R U P B 2
C77 C 0.2031(8) 0.1118(7) 0.3871(6) 0.127(3) Uani 0.6 1 d . . P B 2
H77A H 0.1538 0.1382 0.3575 0.152 Uiso 0.6 1 calc R U P B 2
H77B H 0.2115 0.0410 0.3805 0.152 Uiso 0.6 1 calc R U P B 2
O78 O 0.1644(9) 0.1326(9) 0.4721(9) 0.105(4) Uani 0.5 1 d . . P B 2
C79 C 0.058(2) 0.081(2) 0.522(3) 0.112(10) Uiso 0.3 1 d . . P B 2
H79A H 0.0076 0.0892 0.4900 0.134 Uiso 0.3 1 calc R U P B 2
H79B H 0.0705 0.0119 0.5361 0.134 Uiso 0.3 1 calc R U P B 2
C80 C 0.029(2) 0.1484(19) 0.604(2) 0.131(10) Uani 0.5 1 d . . P B 2
H80A H -0.0349 0.1318 0.6466 0.196 Uiso 0.5 1 calc R U P B 2
H80B H 0.0830 0.1397 0.6315 0.196 Uiso 0.5 1 calc R U P B 2
H80C H 0.0211 0.2157 0.5861 0.196 Uiso 0.5 1 calc R U P B 2
C74A C 0.109(3) 0.164(2) 0.461(2) 0.131(12) Uiso 0.35 1 d . . P C 3
C81 C -0.032(3) 0.295(3) 0.808(2) 0.132(12) Uiso 0.1 1 d . . P D 4
H81A H -0.0980 0.3122 0.8517 0.198 Uiso 0.1 1 calc R U P D 4
H81B H -0.0425 0.2726 0.7552 0.198 Uiso 0.1 1 calc R U P D 4
H81C H 0.0058 0.2435 0.8312 0.198 Uiso 0.1 1 calc R U P D 4
C82 C 0.013(2) 0.360(2) 0.7920(17) 0.106(7) Uiso 0.35 1 d . . P D 4
H82A H -0.0272 0.4125 0.7702 0.127 Uiso 0.35 1 calc R U P D 4
H82B H 0.0211 0.3834 0.8461 0.127 Uiso 0.35 1 calc R U P D 4
O83 O 0.0876(7) 0.3471(8) 0.7434(8) 0.115(5) Uani 0.6 1 d . . P D 4
C84 C 0.083(2) 0.4237(15) 0.6689(14) 0.122(8) Uani 0.5 1 d . . P D 4
H84A H 0.0336 0.4095 0.6393 0.146 Uiso 0.5 1 calc R U P D 4
H84B H 0.0669 0.4905 0.6910 0.146 Uiso 0.5 1 calc R U P D 4
C85 C 0.184(3) 0.406(3) 0.615(3) 0.126(14) Uiso 0.25 1 d . . P D 4
H85A H 0.1956 0.4479 0.5639 0.189 Uiso 0.25 1 calc R U P D 4
H85B H 0.2296 0.4184 0.6478 0.189 Uiso 0.25 1 calc R U P D 4
H85C H 0.1967 0.3384 0.5968 0.189 Uiso 0.25 1 calc R U P D 4
C83A C 0.053(7) 0.359(8) 0.729(6) 0.11(3) Uiso 0.15 1 d . . P E 5
C83B C 0.039(3) 0.421(4) 0.732(3) 0.117(15) Uiso 0.25 1 d . . P E 5
C84A C 0.097(6) 0.466(5) 0.695(5) 0.12(2) Uiso 0.15 1 d . . P E 5
C85A C 0.203(3) 0.417(3) 0.571(2) 0.127(11) Uiso 0.3 1 d . . P F 5
C91 C 0.3147(16) 0.6242(14) 0.6501(13) 0.123(7) Uani 0.5 1 d . . P G 6
H91A H 0.2524 0.6541 0.6404 0.184 Uiso 0.5 1 calc R U P G 6
H91B H 0.3115 0.5545 0.6570 0.184 Uiso 0.5 1 calc R U P G 6
H91C H 0.3216 0.6507 0.7029 0.184 Uiso 0.5 1 calc R U P G 6
C92 C 0.4089(8) 0.6457(5) 0.5697(5) 0.108(2) Uani 0.5 1 d . . P G 6
H92A H 0.3972 0.6211 0.5175 0.129 Uiso 0.5 1 calc R U P G 6
H92B H 0.4071 0.7165 0.5631 0.129 Uiso 0.5 1 calc R U P G 6
O93 O 0.5052(8) 0.6127(6) 0.5659(5) 0.086(2) Uani 0.6 1 d . . P G 6
C94 C 0.5783(14) 0.6439(9) 0.5115(11) 0.101(4) Uani 0.6 1 d . . P G 6
H94A H 0.5725 0.7146 0.5185 0.121 Uiso 0.6 1 calc R U P G 6
H94B H 0.5739 0.6317 0.4530 0.121 Uiso 0.6 1 calc R U P G 6
C95 C 0.6830(12) 0.6032(10) 0.5138(9) 0.129(5) Uani 0.6 1 d . . P G 6
H95A H 0.7351 0.6332 0.4677 0.194 Uiso 0.6 1 calc R U P G 6
H95B H 0.6899 0.6166 0.5706 0.194 Uiso 0.6 1 calc R U P G 6
H95C H 0.6912 0.5334 0.5048 0.194 Uiso 0.6 1 calc R U P G 6
C96 C 0.518(4) 0.675(4) 0.507(4) 0.14(2) Uiso 0.2 1 d . . P H 7
H96A H 0.5098 0.7086 0.4555 0.208 Uiso 0.2 1 calc R U P H 7
H96B H 0.5458 0.7172 0.5393 0.208 Uiso 0.2 1 calc R U P H 7
H96C H 0.5650 0.6166 0.4898 0.208 Uiso 0.2 1 calc R U P H 7
C97 C 0.4089(8) 0.6457(5) 0.5697(5) 0.108(2) Uani 0.5 1 d . . P H 7
H97A H 0.3643 0.7068 0.5813 0.129 Uiso 0.5 1 calc R U P H 7
H97B H 0.3832 0.6075 0.5324 0.129 Uiso 0.5 1 calc R U P H 7
O98 O 0.3855(10) 0.5938(7) 0.6550(7) 0.099(3) Uani 0.5 1 d . . P H 7
C99 C 0.2820(18) 0.5927(18) 0.7066(16) 0.119(8) Uiso 0.4 1 d . . P H 7
H99A H 0.2504 0.6598 0.7098 0.143 Uiso 0.4 1 calc R U P H 7
H99B H 0.2489 0.5558 0.6741 0.143 Uiso 0.4 1 calc R U P H 7
C100 C 0.2563(19) 0.5568(18) 0.7901(16) 0.103(7) Uiso 0.3 1 d . . P H 7
H10A H 0.1822 0.5619 0.8154 0.155 Uiso 0.3 1 calc R U P H 7
H10B H 0.2833 0.4892 0.7893 0.155 Uiso 0.3 1 calc R U P H 7
H10C H 0.2849 0.5939 0.8253 0.155 Uiso 0.3 1 calc R U P H 7
O101 O 0.2860(12) 0.4547(11) 0.8628(7) 0.137(5) Uani 0.45 1 d . . P I 8
C102 C 0.241(4) 0.518(4) 0.872(3) 0.081(14) Uiso 0.15 1 d . . P I 8
C103 C 0.268(5) 0.650(5) 0.816(5) 0.09(2) Uiso 0.1 1 d . . P I 8
C105 C 0.2261(17) 0.6274(17) 0.8904(15) 0.112(7) Uiso 0.35 1 d . . P I 8
C106 C 0.114(3) 0.559(3) 0.926(3) 0.113(12) Uiso 0.2 1 d . . P I 8
C107 C 0.197(2) 0.739(2) 0.9636(18) 0.125(9) Uiso 0.3 1 d . . P I 8
C108 C 0.175(4) 0.445(4) 0.932(3) 0.143(16) Uiso 0.2 1 d . . P I 8
C111 C 0.5657(11) 0.7997(10) 0.7592(9) 0.101(4) Uani 0.5 1 d . . P J 9
H11A H 0.5774 0.8454 0.7102 0.151 Uiso 0.5 1 calc R U P J 9
H11B H 0.5945 0.8213 0.8024 0.151 Uiso 0.5 1 calc R U P J 9
H11C H 0.5982 0.7359 0.7380 0.151 Uiso 0.5 1 calc R U P J 9
C112 C 0.4515(10) 0.7945(12) 0.8012(10) 0.104(5) Uani 0.5 1 d . . P J 9
H11D H 0.4217 0.8611 0.8181 0.125 Uiso 0.5 1 calc R U P J 9
H11E H 0.4255 0.7765 0.7543 0.125 Uiso 0.5 1 calc R U P J 9
O113 O 0.4105(4) 0.7385(3) 0.8698(3) 0.0998(15) Uani 0.6 1 d . . P J 9
C114 C 0.3821(9) 0.8038(9) 0.9519(9) 0.112(5) Uani 0.6 1 d . . P J 9
H11F H 0.4062 0.7697 0.9975 0.134 Uiso 0.6 1 calc R U P J 9
H11G H 0.4164 0.8636 0.9363 0.134 Uiso 0.6 1 calc R U P J 9
C115 C 0.2826(14) 0.8262(13) 0.9830(12) 0.098(5) Uiso 0.4 1 d . . P J 9
H11H H 0.2669 0.8671 1.0344 0.148 Uiso 0.4 1 calc R U P J 9
H11I H 0.2588 0.8609 0.9383 0.148 Uiso 0.4 1 calc R U P J 9
H11J H 0.2486 0.7672 0.9994 0.148 Uiso 0.4 1 calc R U P J 9
O116 O 0.4105(4) 0.7385(3) 0.8698(3) 0.0998(15) Uani 0.4 1 d . . P K 10
C117 C 0.402(2) 0.8339(19) 0.879(2) 0.110(8) Uiso 0.3 1 d . . P K 10
H11K H 0.3504 0.8520 0.9347 0.165 Uiso 0.3 1 calc R U P K 10
H11L H 0.3813 0.8653 0.8312 0.165 Uiso 0.3 1 calc R U P K 10
H11M H 0.4671 0.8544 0.8781 0.165 Uiso 0.3 1 calc R U P K 10
C121 C 0.032(4) 0.405(3) 1.067(3) 0.141(16) Uiso 0.2 1 d . . P L 11
H12A H 0.0916 0.3918 1.0871 0.212 Uiso 0.2 1 calc R U P L 11
H12B H 0.0255 0.4726 1.0501 0.212 Uiso 0.2 1 calc R U P L 11
H12C H -0.0290 0.3908 1.1147 0.212 Uiso 0.2 1 calc R U P L 11
C122 C 0.0435(19) 0.3444(18) 0.9935(16) 0.150(8) Uiso 0.4 1 d . . P L 11
H12D H 0.1082 0.3583 0.9494 0.180 Uiso 0.4 1 calc R U P L 11
H12E H 0.0542 0.2774 1.0133 0.180 Uiso 0.4 1 calc R U P L 11
O123 O -0.0265(17) 0.3437(15) 0.9487(14) 0.148(7) Uiso 0.3 1 d . . P L 11
C124 C 0.004(2) 0.277(2) 0.8760(19) 0.115(8) Uiso 0.3 1 d . . P L 11
H12F H 0.0787 0.2707 0.8527 0.138 Uiso 0.3 1 calc R U P L 11
H12G H -0.0163 0.2127 0.9000 0.138 Uiso 0.3 1 calc R U P L 11
C125 C -0.032(3) 0.295(3) 0.808(2) 0.132(12) Uiso 0.15 1 d . . P L 11
H12H H -0.0050 0.2434 0.7651 0.198 Uiso 0.15 1 calc R U P L 11
H12I H -0.1063 0.2982 0.8287 0.198 Uiso 0.15 1 calc R U P L 11
H12J H -0.0108 0.3565 0.7811 0.198 Uiso 0.15 1 calc R U P L 11
C126 C 0.065(3) 0.443(2) 0.997(2) 0.114(10) Uiso 0.25 1 d . . P M 12
C127 C -0.007(4) 0.195(4) 0.843(3) 0.135(15) Uiso 0.2 1 d . . P N 12
C128 C 0.150(5) 0.780(4) 1.071(4) 0.127(18) Uiso 0.15 1 d . . P O 12
C129 C -0.062(5) 0.238(4) 0.934(4) 0.112(16) Uiso 0.15 1 d . . P N 12
H12 H 0.658(4) 0.071(4) 0.527(4) 0.11(2) Uiso 1 1 d . . . . .
H14 H 0.933(5) 0.204(4) 0.331(4) 0.10(2) Uiso 1 1 d . . . . .
H22 H 0.490(5) 0.479(4) 0.645(4) 0.09(2) Uiso 1 1 d . . . . .
H24 H 0.513(4) 0.654(4) 0.884(4) 0.07(2) Uiso 1 1 d . . . . .
H32 H 0.416(4) 0.348(3) 0.997(3) 0.062(16) Uiso 1 1 d . . . . .
H34 H 0.122(4) 0.238(4) 1.190(4) 0.079(19) Uiso 1 1 d . . . . .
H44 H 0.250(4) 0.065(4) 0.542(3) 0.063(19) Uiso 1 1 d . . . . .
H51 H 0.984(5) 0.129(4) 0.208(4) 0.10(2) Uiso 1 1 d . . . . .
H61 H 1.054(6) 0.334(5) 0.315(5) 0.13(3) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.381(5) . ?
C1 C2 1.412(5) . ?
C1 C10 1.525(5) . ?
C2 C3 1.386(5) . ?
C2 C30 1.522(5) . ?
C3 C4 1.377(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C10 C21 1.520(5) . ?
C10 C11 1.522(5) . ?
C10 H10 0.9800 . ?
C11 C16 1.381(5) . ?
C11 C12 1.404(5) . ?
C12 O12 1.360(4) . ?
C12 C13 1.383(5) . ?
C13 C14 1.373(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(5) . ?
C14 O14 1.380(4) . ?
C15 C16 1.381(5) . ?
C15 Cl15 1.745(4) . ?
C16 H16 0.9300 . ?
O12 H12 0.97(6) . ?
O14 H14 0.89(6) . ?
C21 C26 1.374(5) . ?
C21 C22 1.381(6) . ?
C22 O22 1.366(5) . ?
C22 C23 1.394(6) . ?
C23 C24 1.369(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.362(6) . ?
C24 O24 1.377(5) . ?
C25 C26 1.383(6) . ?
C25 Cl25 1.750(4) . ?
C26 H26 0.9300 . ?
O22 H22 0.82(6) . ?
O24 H24 0.82(5) . ?
C30 C31 1.520(5) . ?
C30 C41 1.531(5) . ?
C30 H30 0.9800 . ?
C31 C36 1.374(5) . ?
C31 C32 1.399(5) . ?
C32 O32 1.357(4) . ?
C32 C33 1.383(5) . ?
C33 C34 1.381(5) . ?
C33 H33 0.9300 . ?
C34 O34 1.377(4) . ?
C34 C35 1.377(5) . ?
C35 C36 1.388(5) . ?
C35 Cl35 1.743(4) . ?
C36 H36 0.9300 . ?
O32 H32 0.81(5) . ?
O34 H34 0.80(5) . ?
C41 C42 1.376(6) . ?
C41 C46 1.378(5) . ?
C42 O42 1.376(5) . ?
C42 C43 1.401(6) . ?
C43 C44 1.373(6) . ?
C43 H43 0.9300 . ?
C44 O44 1.361(5) . ?
C44 C45 1.368(6) . ?
C45 C46 1.395(5) . ?
C45 Cl45 1.736(4) . ?
C46 H46 0.9300 . ?
O44 H44 0.78(5) . ?
O51 C52 1.413(7) . ?
O51 H51 0.86(6) . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
O61 C62 1.385(6) . ?
O61 H61 0.86(7) . ?
C62 H62A 0.9600 . ?
C62 H62B 0.9600 . ?
C62 H62C 0.9600 . ?
C71 C72 1.29(3) . ?
C71 H71A 0.9600 . ?
C71 H71B 0.9600 . ?
C71 H71C 0.9600 . ?
C72 O73 1.43(2) . ?
C72 H72A 0.9700 . ?
C72 H72B 0.9700 . ?
O73 C74 1.25(3) . ?
C74 C75 1.61(4) . ?
C74 H74A 0.9700 . ?
C74 H74B 0.9700 . ?
C75 H75A 0.9600 . ?
C75 H75B 0.9600 . ?
C75 H75C 0.9600 . ?
C76 C77 1.398(17) . ?
C76 H76A 0.9600 . ?
C76 H76B 0.9600 . ?
C76 H76C 0.9600 . ?
C77 O78 1.312(15) . ?
C77 H77A 0.9700 . ?
C77 H77B 0.9700 . ?
O78 C79 1.64(3) . ?
C79 C80 1.55(5) . ?
C79 H79A 0.9700 . ?
C79 H79B 0.9700 . ?
C80 H80A 0.9600 . ?
C80 H80B 0.9600 . ?
C80 H80C 0.9600 . ?
C81 C82 1.11(4) . ?
C81 H81A 0.9600 . ?
C81 H81B 0.9600 . ?
C81 H81C 0.9600 . ?
C82 O83 1.07(3) . ?
C82 H82A 0.9700 . ?
C82 H82B 0.9700 . ?
O83 C84 1.56(2) . ?
C84 C85 1.38(4) . ?
C84 H84A 0.9700 . ?
C84 H84B 0.9700 . ?
C85 H85A 0.9600 . ?
C85 H85B 0.9600 . ?
C85 H85C 0.9600 . ?
C83A C83B 0.84(11) . ?
C83A C84A 1.64(12) . ?
C83B C84A 1.07(7) . ?
C91 C92 1.54(2) . ?
C91 H91A 0.9600 . ?
C91 H91B 0.9600 . ?
C91 H91C 0.9600 . ?
C92 O93 1.330(11) . ?
C92 H92A 0.9700 . ?
C92 H92B 0.9700 . ?
O93 C94 1.200(15) . ?
C94 C95 1.492(18) . ?
C94 H94A 0.9700 . ?
C94 H94B 0.9700 . ?
C95 H95A 0.9600 . ?
C95 H95B 0.9600 . ?
C95 H95C 0.9600 . ?
C96 C97 1.59(6) . ?
C96 H96A 0.9600 . ?
C96 H96B 0.9600 . ?
C96 H96C 0.9600 . ?
C97 O98 1.460(12) . ?
C97 H97A 0.9700 . ?
C97 H97B 0.9699 . ?
O98 C99 1.39(2) . ?
C99 C100 1.34(3) . ?
C99 H99A 0.9700 . ?
C99 H99B 0.9700 . ?
C100 H10A 0.9600 . ?
C100 H10B 0.9600 . ?
C100 H10C 0.9600 . ?
O101 C102 1.00(5) . ?
O101 C108 1.58(5) . ?
C102 C105 1.51(5) . ?
C102 C108 1.51(7) . ?
C102 C106 1.71(6) . ?
C102 C103 1.99(9) . ?
C103 C105 1.18(7) . ?
C105 C106 1.81(4) . ?
C105 C107 1.88(3) . ?
C106 C108 1.70(6) . ?
C111 C112 1.499(17) . ?
C111 H11A 0.9600 . ?
C111 H11B 0.9600 . ?
C111 H11C 0.9600 . ?
C112 O113 1.312(14) . ?
C112 H11D 0.9700 . ?
C112 H11E 0.9700 . ?
O113 C114 1.531(11) . ?
C114 C115 1.299(18) . ?
C114 H11F 0.9700 . ?
C114 H11G 0.9700 . ?
C115 H11H 0.9600 . ?
C115 H11I 0.9600 . ?
C115 H11J 0.9600 . ?
O116 C117 1.31(3) . ?
C117 H11K 0.9600 . ?
C117 H11L 0.9600 . ?
C117 H11M 0.9600 . ?
C121 C122 1.42(4) . ?
C121 H12A 0.9600 . ?
C121 H12B 0.9600 . ?
C121 H12C 0.9600 . ?
C122 O123 1.36(3) . ?
C122 H12D 0.9700 . ?
C122 H12E 0.9700 . ?
O123 C124 1.43(3) . ?
C124 C125 1.32(4) . ?
C124 H12F 0.9700 . ?
C124 H12G 0.9700 . ?
C125 H12H 0.9600 . ?
C125 H12I 0.9600 . ?
C125 H12J 0.9601 . ?
C127 C129 1.50(6) . ?
C127 C128 2.01(7) 2_567 ?
C128 C129 1.28(7) 2_567 ?
C128 C127 2.01(7) 2_567 ?
C129 C128 1.28(7) 2_567 ?

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 119.1(4) . . ?
C6 C1 C10 120.9(3) . . ?
C2 C1 C10 120.0(4) . . ?
C3 C2 C1 118.4(4) . . ?
C3 C2 C30 120.8(3) . . ?
C1 C2 C30 120.7(3) . . ?
C4 C3 C2 121.6(4) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.3(4) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 121.6(4) . . ?
C1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C21 C10 C11 112.9(3) . . ?
C21 C10 C1 111.1(3) . . ?
C11 C10 C1 113.3(3) . . ?
C21 C10 H10 106.3 . . ?
C11 C10 H10 106.3 . . ?
C1 C10 H10 106.3 . . ?
C16 C11 C12 116.9(3) . . ?
C16 C11 C10 123.5(3) . . ?
C12 C11 C10 119.5(3) . . ?
O12 C12 C13 122.2(3) . . ?
O12 C12 C11 116.4(3) . . ?
C13 C12 C11 121.4(3) . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.3(3) . . ?
C13 C14 O14 121.8(3) . . ?
C15 C14 O14 118.9(3) . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 Cl15 119.6(3) . . ?
C16 C15 Cl15 119.9(3) . . ?
C11 C16 C15 121.7(3) . . ?
C11 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C12 O12 H12 107(3) . . ?
C14 O14 H14 112(4) . . ?
C26 C21 C22 117.0(3) . . ?
C26 C21 C10 122.7(4) . . ?
C22 C21 C10 120.3(3) . . ?
O22 C22 C21 117.6(3) . . ?
O22 C22 C23 121.1(4) . . ?
C21 C22 C23 121.4(4) . . ?
C24 C23 C22 120.1(5) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 119.2(4) . . ?
C25 C24 O24 118.6(4) . . ?
C23 C24 O24 122.1(5) . . ?
C24 C25 C26 120.4(4) . . ?
C24 C25 Cl25 119.8(3) . . ?
C26 C25 Cl25 119.7(4) . . ?
C21 C26 C25 121.8(4) . . ?
C21 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
C22 O22 H22 112(4) . . ?
C24 O24 H24 113(4) . . ?
C31 C30 C2 113.1(3) . . ?
C31 C30 C41 112.1(3) . . ?
C2 C30 C41 111.7(3) . . ?
C31 C30 H30 106.5 . . ?
C2 C30 H30 106.5 . . ?
C41 C30 H30 106.5 . . ?
C36 C31 C32 117.5(3) . . ?
C36 C31 C30 123.8(3) . . ?
C32 C31 C30 118.6(3) . . ?
O32 C32 C33 122.3(3) . . ?
O32 C32 C31 116.6(3) . . ?
C33 C32 C31 121.1(3) . . ?
C34 C33 C32 120.2(3) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
O34 C34 C35 118.6(3) . . ?
O34 C34 C33 122.0(3) . . ?
C35 C34 C33 119.4(3) . . ?
C34 C35 C36 120.0(3) . . ?
C34 C35 Cl35 120.0(3) . . ?
C36 C35 Cl35 119.9(3) . . ?
C31 C36 C35 121.8(3) . . ?
C31 C36 H36 119.1 . . ?
C35 C36 H36 119.1 . . ?
C32 O32 H32 110(3) . . ?
C34 O34 H34 108(4) . . ?
C42 C41 C46 117.6(3) . . ?
C42 C41 C30 120.3(3) . . ?
C46 C41 C30 122.1(4) . . ?
O42 C42 C41 118.5(3) . . ?
O42 C42 C43 120.0(4) . . ?
C41 C42 C43 121.5(4) . . ?
C44 C43 C42 120.1(4) . . ?
C44 C43 H43 120.0 . . ?
C42 C43 H43 120.0 . . ?
O44 C44 C45 118.2(4) . . ?
O44 C44 C43 122.9(4) . . ?
C45 C44 C43 118.9(4) . . ?
C44 C45 C46 120.8(4) . . ?
C44 C45 Cl45 119.6(3) . . ?
C46 C45 Cl45 119.6(3) . . ?
C41 C46 C45 121.1(4) . . ?
C41 C46 H46 119.5 . . ?
C45 C46 H46 119.5 . . ?
C44 O44 H44 112(4) . . ?
C52 O51 H51 113(4) . . ?
O51 C52 H52A 109.5 . . ?
O51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
O51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C62 O61 H61 113(5) . . ?
O61 C62 H62A 109.5 . . ?
O61 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
O61 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
C72 C71 H71A 109.5 . . ?
C72 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
C72 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
C71 C72 O73 121(2) . . ?
C71 C72 H72A 107.0 . . ?
O73 C72 H72A 107.0 . . ?
C71 C72 H72B 107.0 . . ?
O73 C72 H72B 107.0 . . ?
H72A C72 H72B 106.8 . . ?
C74 O73 C72 111(3) . . ?
O73 C74 C75 112(3) . . ?
O73 C74 H74A 109.1 . . ?
C75 C74 H74A 109.1 . . ?
O73 C74 H74B 109.1 . . ?
C75 C74 H74B 109.1 . . ?
H74A C74 H74B 107.8 . . ?
C74 C75 H75A 109.5 . . ?
C74 C75 H75B 109.5 . . ?
H75A C75 H75B 109.5 . . ?
C74 C75 H75C 109.5 . . ?
H75A C75 H75C 109.5 . . ?
H75B C75 H75C 109.5 . . ?
C77 C76 H76A 109.5 . . ?
C77 C76 H76B 109.5 . . ?
H76A C76 H76B 109.5 . . ?
C77 C76 H76C 109.5 . . ?
H76A C76 H76C 109.5 . . ?
H76B C76 H76C 109.5 . . ?
O78 C77 C76 114.3(12) . . ?
O78 C77 H77A 108.7 . . ?
C76 C77 H77A 108.7 . . ?
O78 C77 H77B 108.7 . . ?
C76 C77 H77B 108.7 . . ?
H77A C77 H77B 107.6 . . ?
C77 O78 C79 113.3(19) . . ?
C80 C79 O78 93(2) . . ?
C80 C79 H79A 113.1 . . ?
O78 C79 H79A 113.1 . . ?
C80 C79 H79B 113.1 . . ?
O78 C79 H79B 113.1 . . ?
H79A C79 H79B 110.5 . . ?
C79 C80 H80A 109.5 . . ?
C79 C80 H80B 109.5 . . ?
H80A C80 H80B 109.5 . . ?
C79 C80 H80C 109.5 . . ?
H80A C80 H80C 109.5 . . ?
H80B C80 H80C 109.5 . . ?
C82 C81 H81A 109.5 . . ?
C82 C81 H81B 109.5 . . ?
H81A C81 H81B 109.5 . . ?
C82 C81 H81C 109.5 . . ?
H81A C81 H81C 109.5 . . ?
H81B C81 H81C 109.5 . . ?
O83 C82 C81 114(3) . . ?
O83 C82 H82A 108.7 . . ?
C81 C82 H82A 108.8 . . ?
O83 C82 H82B 108.7 . . ?
C81 C82 H82B 108.7 . . ?
H82A C82 H82B 107.6 . . ?
C82 O83 C84 102.8(19) . . ?
C85 C84 O83 98(2) . . ?
C85 C84 H84A 112.3 . . ?
O83 C84 H84A 112.3 . . ?
C85 C84 H84B 112.2 . . ?
O83 C84 H84B 112.2 . . ?
H84A C84 H84B 109.9 . . ?
C84 C85 H85A 109.5 . . ?
C84 C85 H85B 109.5 . . ?
H85A C85 H85B 109.5 . . ?
C84 C85 H85C 109.5 . . ?
H85A C85 H85C 109.5 . . ?
H85B C85 H85C 109.5 . . ?
C83B C83A C84A 35(6) . . ?
C83A C83B C84A 118(9) . . ?
C83B C84A C83A 27(5) . . ?
C92 C91 H91A 109.5 . . ?
C92 C91 H91B 109.5 . . ?
H91A C91 H91B 109.5 . . ?
C92 C91 H91C 109.5 . . ?
H91A C91 H91C 109.5 . . ?
H91B C91 H91C 109.5 . . ?
O93 C92 C91 122.0(10) . . ?
O93 C92 H92A 106.8 . . ?
C91 C92 H92A 106.8 . . ?
O93 C92 H92B 106.8 . . ?
C91 C92 H92B 106.8 . . ?
H92A C92 H92B 106.7 . . ?
C94 O93 C92 121.0(11) . . ?
O93 C94 C95 116.7(14) . . ?
O93 C94 H94A 108.1 . . ?
C95 C94 H94A 108.1 . . ?
O93 C94 H94B 108.1 . . ?
C95 C94 H94B 108.1 . . ?
H94A C94 H94B 107.3 . . ?
C94 C95 H95A 109.5 . . ?
C94 C95 H95B 109.5 . . ?
H95A C95 H95B 109.5 . . ?
C94 C95 H95C 109.5 . . ?
H95A C95 H95C 109.5 . . ?
H95B C95 H95C 109.5 . . ?
C97 C96 H96A 109.5 . . ?
C97 C96 H96B 109.5 . . ?
H96A C96 H96B 109.5 . . ?
C97 C96 H96C 109.5 . . ?
H96A C96 H96C 109.5 . . ?
H96B C96 H96C 109.5 . . ?
O98 C97 C96 128(2) . . ?
O98 C97 H97A 105.3 . . ?
C96 C97 H97A 105.3 . . ?
O98 C97 H97B 105.3 . . ?
C96 C97 H97B 105.3 . . ?
H97A C97 H97B 106.0 . . ?
C99 O98 C97 118.3(16) . . ?
C100 C99 O98 121(2) . . ?
C100 C99 H99A 107.1 . . ?
O98 C99 H99A 107.1 . . ?
C100 C99 H99B 107.1 . . ?
O98 C99 H99B 107.1 . . ?
H99A C99 H99B 106.8 . . ?
C99 C100 H10A 109.5 . . ?
C99 C100 H10B 109.5 . . ?
H10A C100 H10B 109.5 . . ?
C99 C100 H10C 109.5 . . ?
H10A C100 H10C 109.5 . . ?
H10B C100 H10C 109.5 . . ?
C102 O101 C108 67(4) . . ?
O101 C102 C105 149(5) . . ?
O101 C102 C108 75(4) . . ?
C105 C102 C108 123(4) . . ?
O101 C102 C106 138(5) . . ?
C105 C102 C106 68(3) . . ?
C108 C102 C106 63(3) . . ?
O101 C102 C103 131(5) . . ?
C105 C102 C103 36(2) . . ?
C108 C102 C103 155(4) . . ?
C106 C102 C103 92(3) . . ?
C105 C103 C102 49(3) . . ?
C103 C105 C102 95(4) . . ?
C103 C105 C106 125(4) . . ?
C102 C105 C106 61(2) . . ?
C103 C105 C107 110(4) . . ?
C102 C105 C107 155(3) . . ?
C106 C105 C107 107.5(19) . . ?
C108 C106 C102 53(3) . . ?
C108 C106 C105 99(3) . . ?
C102 C106 C105 51(2) . . ?
C102 C108 O101 38(2) . . ?
C102 C108 C106 64(3) . . ?
O101 C108 C106 102(3) . . ?
C112 C111 H11A 109.5 . . ?
C112 C111 H11B 109.5 . . ?
H11A C111 H11B 109.5 . . ?
C112 C111 H11C 109.5 . . ?
H11A C111 H11C 109.5 . . ?
H11B C111 H11C 109.5 . . ?
O113 C112 C111 124.2(12) . . ?
O113 C112 H11D 106.3 . . ?
C111 C112 H11D 106.3 . . ?
O113 C112 H11E 106.3 . . ?
C111 C112 H11E 106.3 . . ?
H11D C112 H11E 106.4 . . ?
C112 O113 C114 106.2(9) . . ?
C115 C114 O113 111.2(12) . . ?
C115 C114 H11F 109.4 . . ?
O113 C114 H11F 109.4 . . ?
C115 C114 H11G 109.4 . . ?
O113 C114 H11G 109.4 . . ?
H11F C114 H11G 108.0 . . ?
C114 C115 H11H 109.5 . . ?
C114 C115 H11I 109.5 . . ?
H11H C115 H11I 109.5 . . ?
C114 C115 H11J 109.5 . . ?
H11H C115 H11J 109.5 . . ?
H11I C115 H11J 109.5 . . ?
O116 C117 H11K 109.5 . . ?
O116 C117 H11L 109.5 . . ?
H11K C117 H11L 109.5 . . ?
O116 C117 H11M 109.5 . . ?
H11K C117 H11M 109.5 . . ?
H11L C117 H11M 109.5 . . ?
C122 C121 H12A 109.5 . . ?
C122 C121 H12B 109.5 . . ?
H12A C121 H12B 109.5 . . ?
C122 C121 H12C 109.5 . . ?
H12A C121 H12C 109.5 . . ?
H12B C121 H12C 109.5 . . ?
O123 C122 C121 125(3) . . ?
O123 C122 H12D 106.0 . . ?
C121 C122 H12D 106.0 . . ?
O123 C122 H12E 106.0 . . ?
C121 C122 H12E 106.0 . . ?
H12D C122 H12E 106.3 . . ?
C122 O123 C124 114(2) . . ?
C125 C124 O123 120(3) . . ?
C125 C124 H12F 107.4 . . ?
O123 C124 H12F 107.4 . . ?
C125 C124 H12G 107.4 . . ?
O123 C124 H12G 107.4 . . ?
H12F C124 H12G 107.0 . . ?
C124 C125 H12H 109.5 . . ?
C124 C125 H12I 109.5 . . ?
H12H C125 H12I 109.5 . . ?
C124 C125 H12J 109.5 . . ?
H12H C125 H12J 109.5 . . ?
H12I C125 H12J 109.5 . . ?
C129 C127 C128 40(3) . 2_567 ?
C129 C128 C127 49(3) 2_567 2_567 ?
C128 C129 C127 92(5) 2_567 . ?

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 0.1(5) . . . . ?
C10 C1 C2 C3 -178.1(3) . . . . ?
C6 C1 C2 C30 -176.7(3) . . . . ?
C10 C1 C2 C30 5.2(5) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C30 C2 C3 C4 176.8(3) . . . . ?
C2 C3 C4 C5 0.1(6) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
C10 C1 C6 C5 177.8(3) . . . . ?
C4 C5 C6 C1 0.4(6) . . . . ?
C6 C1 C10 C21 -99.0(4) . . . . ?
C2 C1 C10 C21 79.1(4) . . . . ?
C6 C1 C10 C11 29.4(4) . . . . ?
C2 C1 C10 C11 -152.5(3) . . . . ?
C21 C10 C11 C16 14.3(5) . . . . ?
C1 C10 C11 C16 -113.1(4) . . . . ?
C21 C10 C11 C12 -162.2(4) . . . . ?
C1 C10 C11 C12 70.4(4) . . . . ?
C16 C11 C12 O12 179.9(4) . . . . ?
C10 C11 C12 O12 -3.3(5) . . . . ?
C16 C11 C12 C13 -1.1(6) . . . . ?
C10 C11 C12 C13 175.7(4) . . . . ?
O12 C12 C13 C14 179.0(4) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C12 C13 C14 C15 2.0(7) . . . . ?
C12 C13 C14 O14 -177.8(4) . . . . ?
C13 C14 C15 C16 -3.0(7) . . . . ?
O14 C14 C15 C16 176.9(4) . . . . ?
C13 C14 C15 Cl15 178.1(3) . . . . ?
O14 C14 C15 Cl15 -2.0(6) . . . . ?
C12 C11 C16 C15 0.1(6) . . . . ?
C10 C11 C16 C15 -176.5(4) . . . . ?
C14 C15 C16 C11 1.9(7) . . . . ?
Cl15 C15 C16 C11 -179.2(3) . . . . ?
C11 C10 C21 C26 -97.0(4) . . . . ?
C1 C10 C21 C26 31.6(5) . . . . ?
C11 C10 C21 C22 83.6(4) . . . . ?
C1 C10 C21 C22 -147.8(4) . . . . ?
C26 C21 C22 O22 177.9(4) . . . . ?
C10 C21 C22 O22 -2.7(6) . . . . ?
C26 C21 C22 C23 -1.2(6) . . . . ?
C10 C21 C22 C23 178.2(4) . . . . ?
O22 C22 C23 C24 -179.0(4) . . . . ?
C21 C22 C23 C24 0.1(7) . . . . ?
C22 C23 C24 C25 1.8(7) . . . . ?
C22 C23 C24 O24 179.9(4) . . . . ?
C23 C24 C25 C26 -2.6(6) . . . . ?
O24 C24 C25 C26 179.3(4) . . . . ?
C23 C24 C25 Cl25 178.8(3) . . . . ?
O24 C24 C25 Cl25 0.7(6) . . . . ?
C22 C21 C26 C25 0.4(6) . . . . ?
C10 C21 C26 C25 -179.0(3) . . . . ?
C24 C25 C26 C21 1.5(6) . . . . ?
Cl25 C25 C26 C21 -179.9(3) . . . . ?
C3 C2 C30 C31 31.9(4) . . . . ?
C1 C2 C30 C31 -151.4(3) . . . . ?
C3 C2 C30 C41 -95.7(4) . . . . ?
C1 C2 C30 C41 81.0(4) . . . . ?
C2 C30 C31 C36 -106.0(4) . . . . ?
C41 C30 C31 C36 21.4(5) . . . . ?
C2 C30 C31 C32 74.9(4) . . . . ?
C41 C30 C31 C32 -157.8(4) . . . . ?
C36 C31 C32 O32 -179.6(4) . . . . ?
C30 C31 C32 O32 -0.5(6) . . . . ?
C36 C31 C32 C33 -0.3(6) . . . . ?
C30 C31 C32 C33 178.9(4) . . . . ?
O32 C32 C33 C34 179.0(4) . . . . ?
C31 C32 C33 C34 -0.4(7) . . . . ?
C32 C33 C34 O34 -179.6(4) . . . . ?
C32 C33 C34 C35 0.6(7) . . . . ?
O34 C34 C35 C36 180.0(4) . . . . ?
C33 C34 C35 C36 -0.2(7) . . . . ?
O34 C34 C35 Cl35 1.0(6) . . . . ?
C33 C34 C35 Cl35 -179.2(3) . . . . ?
C32 C31 C36 C35 0.6(6) . . . . ?
C30 C31 C36 C35 -178.5(4) . . . . ?
C34 C35 C36 C31 -0.4(7) . . . . ?
Cl35 C35 C36 C31 178.6(3) . . . . ?
C31 C30 C41 C42 70.5(4) . . . . ?
C2 C30 C41 C42 -161.4(3) . . . . ?
C31 C30 C41 C46 -108.6(4) . . . . ?
C2 C30 C41 C46 19.5(5) . . . . ?
C46 C41 C42 O42 179.3(4) . . . . ?
C30 C41 C42 O42 0.2(6) . . . . ?
C46 C41 C42 C43 0.7(6) . . . . ?
C30 C41 C42 C43 -178.4(4) . . . . ?
O42 C42 C43 C44 -179.4(4) . . . . ?
C41 C42 C43 C44 -0.9(7) . . . . ?
C42 C43 C44 O44 178.6(4) . . . . ?
C42 C43 C44 C45 1.1(6) . . . . ?
O44 C44 C45 C46 -178.9(4) . . . . ?
C43 C44 C45 C46 -1.2(6) . . . . ?
O44 C44 C45 Cl45 3.0(5) . . . . ?
C43 C44 C45 Cl45 -179.3(3) . . . . ?
C42 C41 C46 C45 -0.8(5) . . . . ?
C30 C41 C46 C45 178.2(3) . . . . ?
C44 C45 C46 C41 1.1(6) . . . . ?
Cl45 C45 C46 C41 179.2(3) . . . . ?
C71 C72 O73 C74 167(3) . . . . ?
C72 O73 C74 C75 179(2) . . . . ?
C76 C77 O78 C79 -175.0(16) . . . . ?
C77 O78 C79 C80 -164.6(17) . . . . ?
C81 C82 O83 C84 122(3) . . . . ?
C82 O83 C84 C85 175(2) . . . . ?
C91 C92 O93 C94 -166.5(12) . . . . ?
C92 O93 C94 C95 179.0(9) . . . . ?
C96 C97 O98 C99 168(3) . . . . ?
C97 O98 C99 C100 -171.7(19) . . . . ?
C108 O101 C102 C105 130(10) . . . . ?
C108 O101 C102 C106 -8(6) . . . . ?
C108 O101 C102 C103 -180(6) . . . . ?
C102 C103 C105 C106 -58(4) . . . . ?
C102 C103 C105 C107 173(3) . . . . ?
O101 C102 C105 C103 82(10) . . . . ?
C108 C102 C105 C103 -160(5) . . . . ?
C106 C102 C105 C103 -127(4) . . . . ?
O101 C102 C105 C106 -151(10) . . . . ?
C108 C102 C105 C106 -32(4) . . . . ?
C103 C102 C105 C106 127(4) . . . . ?
O101 C102 C105 C107 -82(12) . . . . ?
C108 C102 C105 C107 37(9) . . . . ?
C106 C102 C105 C107 69(6) . . . . ?
C103 C102 C105 C107 -164(8) . . . . ?
O101 C102 C106 C108 8(6) . . . . ?
C105 C102 C106 C108 -150(4) . . . . ?
C103 C102 C106 C108 -178(4) . . . . ?
O101 C102 C106 C105 158(8) . . . . ?
C108 C102 C106 C105 150(4) . . . . ?
C103 C102 C106 C105 -28(2) . . . . ?
C103 C105 C106 C108 98(5) . . . . ?
C102 C105 C106 C108 24(3) . . . . ?
C107 C105 C106 C108 -132(2) . . . . ?
C103 C105 C106 C102 74(5) . . . . ?
C107 C105 C106 C102 -155(3) . . . . ?
C105 C102 C108 O101 -152(6) . . . . ?
C106 C102 C108 O101 174(4) . . . . ?
C103 C102 C108 O101 179(11) . . . . ?
O101 C102 C108 C106 -174(4) . . . . ?
C105 C102 C108 C106 34(4) . . . . ?
C103 C102 C108 C106 5(9) . . . . ?
C102 O101 C108 C106 5(4) . . . . ?
C105 C106 C108 C102 -23(3) . . . . ?
C102 C106 C108 O101 -4(3) . . . . ?
C105 C106 C108 O101 -27(3) . . . . ?
C111 C112 O113 C114 96.4(15) . . . . ?
C112 O113 C114 C115 106.2(15) . . . . ?
C121 C122 O123 C124 180(3) . . . . ?
C122 O123 C124 C125 -153(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
O12 H12 O44 0.97(6) 1.86(6) 2.817(4) 171(5) 2_656
O14 H14 O51 0.89(6) 1.74(6) 2.626(4) 174(6) .
O22 H22 O98 0.82(6) 1.98(6) 2.753(11) 157(6) .
O22 H22 O93 0.82(6) 2.16(6) 2.905(9) 151(6) .
O24 H24 O113 0.82(5) 1.79(6) 2.610(6) 180(6) .
O32 H32 O24 0.81(5) 2.01(5) 2.752(4) 151(5) 2_667
O34 H34 O61 0.80(5) 1.87(5) 2.659(4) 168(5) 1_456
O44 H44 O78 0.78(5) 1.99(5) 2.745(15) 162(5) .
O44 H44 O73 0.78(5) 1.99(5) 2.708(10) 154(5) .
O51 H51 O34 0.86(6) 2.00(6) 2.759(5) 147(5) 1_654
O51 H51 Cl35 0.86(6) 2.79(6) 3.489(4) 139(5) 1_654
O61 H61 O14 0.86(7) 2.01(7) 2.741(4) 142(6) .
O61 H61 Cl15 0.86(7) 2.79(7) 3.517(3) 142(6) .

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_marcoc1c
_database_code_depnum_ccdc_archive 'CCDC 1497843'
_audit_update_record             
;
2016-08-05 deposited with the CCDC.
2016-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_structural     '{1,2-C6H4(CH)2}(OC6H2-OH-3,Cl-4)2, Et2O'
_chemical_formula_moiety         'C20 H12 Cl2 O4, C4 H10 O'
_chemical_formula_sum            'C24 H22 Cl2 O5'
_chemical_formula_weight         461.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.3214(6)
_cell_length_b                   11.6802(5)
_cell_length_c                   15.2837(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.433(4)
_cell_angle_gamma                90
_cell_volume                     2098.54(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    3914
_cell_measurement_theta_min      3.0674
_cell_measurement_theta_max      32.5839

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.345
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91389
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro, Agilent Technologies, Version 1.171.36.21 
 Empirical absorption correction using spherical harmonics,
  implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      140(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur 3/Sapphire3 CCD'
_diffrn_measurement_method       'Thin slice φ and ω scans'
_diffrn_detector_area_resol_mean 16.0050
_diffrn_reflns_number            29087
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.074
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3688
_reflns_number_gt                2842
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies, Version 1.171.36.21 
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies, Version 1.171.36.21 
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies, Version 1.171.36.21 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976 and Farrugia, 2012)'
_computing_publication_material  
'SHELXL-2014/7 (Sheldrick, 2015) and WINGX (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0312P)²+0.7849P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3688
_refine_ls_number_parameters     288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0776
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.12823(18) 0.49028(18) 0.67647(14) 0.0180(5) Uani 1 1 d . . . . .
C2 C 0.05435(18) 0.58035(18) 0.64012(14) 0.0189(5) Uani 1 1 d . . . . .
C3 C -0.05761(19) 0.5576(2) 0.58905(15) 0.0224(5) Uani 1 1 d . . . . .
H3 H -0.1070 0.6178 0.5649 0.027 Uiso 1 1 calc R U . . .
C4 C -0.0956(2) 0.4459(2) 0.57412(15) 0.0267(6) Uani 1 1 d . . . . .
H4 H -0.1705 0.4310 0.5402 0.032 Uiso 1 1 calc R U . . .
C5 C -0.0222(2) 0.3564(2) 0.60965(15) 0.0264(6) Uani 1 1 d . . . . .
H5 H -0.0476 0.2813 0.5991 0.032 Uiso 1 1 calc R U . . .
C6 C 0.08896(19) 0.37845(19) 0.66083(15) 0.0223(5) Uani 1 1 d . . . . .
H6 H 0.1378 0.3179 0.6850 0.027 Uiso 1 1 calc R U . . .
C7 C 0.24834(17) 0.51860(18) 0.73446(14) 0.0170(5) Uani 1 1 d . . . . .
H7 H 0.2866 0.4453 0.7540 0.020 Uiso 1 1 calc R U . . .
C8 C 0.09201(18) 0.70238(18) 0.65626(15) 0.0191(5) Uani 1 1 d . . . . .
H8 H 0.0253 0.7474 0.6231 0.023 Uiso 1 1 calc R U . . .
C11 C 0.24743(17) 0.58128(18) 0.82141(14) 0.0171(5) Uani 1 1 d . . . . .
C12 C 0.18337(17) 0.67891(18) 0.82417(14) 0.0178(5) Uani 1 1 d . . . . .
O12 O 0.11847(12) 0.74022(12) 0.74913(10) 0.0220(4) Uani 1 1 d . . . . .
C13 C 0.18174(18) 0.72648(18) 0.90684(15) 0.0197(5) Uani 1 1 d . . . . .
H13 H 0.1379 0.7914 0.9065 0.024 Uiso 1 1 calc R U . . .
C14 C 0.24369(18) 0.67968(19) 0.98971(15) 0.0199(5) Uani 1 1 d . . . . .
O14 O 0.24244(14) 0.72344(15) 1.07221(11) 0.0270(4) Uani 1 1 d . . . . .
C15 C 0.31076(18) 0.58412(19) 0.98807(15) 0.0203(5) Uani 1 1 d . . . . .
Cl15 Cl 0.39315(5) 0.52344(6) 1.09118(4) 0.02997(16) Uani 1 1 d . . . . .
C16 C 0.31095(17) 0.53586(19) 0.90567(14) 0.0192(5) Uani 1 1 d . . . . .
H16 H 0.3549 0.4709 0.9063 0.023 Uiso 1 1 calc R U . . .
C21 C 0.31518(17) 0.57895(18) 0.67855(14) 0.0164(5) Uani 1 1 d . . . . .
O22 O 0.17937(12) 0.73723(12) 0.61833(10) 0.0225(4) Uani 1 1 d . . . . .
C22 C 0.27779(17) 0.67637(18) 0.62552(14) 0.0175(5) Uani 1 1 d . . . . .
C23 C 0.34154(18) 0.72399(19) 0.57300(14) 0.0191(5) Uani 1 1 d . . . . .
H23 H 0.3147 0.7888 0.5378 0.023 Uiso 1 1 calc R U . . .
C24 C 0.44431(18) 0.67591(18) 0.57272(14) 0.0184(5) Uani 1 1 d . . . . .
O24 O 0.50982(13) 0.71962(14) 0.52290(11) 0.0242(4) Uani 1 1 d . . . . .
C25 C 0.48324(18) 0.57987(18) 0.62664(14) 0.0185(5) Uani 1 1 d . . . . .
Cl25 Cl 0.61266(5) 0.51893(5) 0.62763(4) 0.02627(15) Uani 1 1 d . . . . .
C26 C 0.41921(17) 0.53237(18) 0.67769(14) 0.0172(5) Uani 1 1 d . . . . .
H26 H 0.4462 0.4674 0.7126 0.021 Uiso 1 1 calc R U . . .
C31 C 0.4758(2) 1.0307(2) 0.34625(16) 0.0301(6) Uani 1 1 d . . . . .
H31A H 0.4634 1.1119 0.3440 0.045 Uiso 1 1 calc R U . . .
H31B H 0.5506 1.0142 0.3862 0.045 Uiso 1 1 calc R U . . .
H31C H 0.4691 1.0028 0.2858 0.045 Uiso 1 1 calc R U . . .
C32 C 0.3888(2) 0.9731(2) 0.38203(16) 0.0276(5) Uani 1 1 d . . . . .
H32A H 0.3949 1.0025 0.4427 0.033 Uiso 1 1 calc R U . . .
H32B H 0.3133 0.9911 0.3422 0.033 Uiso 1 1 calc R U . . .
O33 O 0.40325(14) 0.85174(14) 0.38691(11) 0.0341(4) Uani 1 1 d . . . . .
C34 C 0.3542(2) 0.7923(2) 0.30131(17) 0.0319(6) Uani 1 1 d . . . . .
H34A H 0.4022 0.7280 0.2971 0.038 Uiso 1 1 calc R U . . .
H34B H 0.3504 0.8436 0.2506 0.038 Uiso 1 1 calc R U . . .
C35 C 0.2375(2) 0.7502(2) 0.29453(18) 0.0380(7) Uani 1 1 d . . . . .
H35A H 0.2064 0.7110 0.2372 0.057 Uiso 1 1 calc R U . . .
H35B H 0.2414 0.6985 0.3442 0.057 Uiso 1 1 calc R U . . .
H35C H 0.1897 0.8140 0.2977 0.057 Uiso 1 1 calc R U . . .
H14 H 0.182(2) 0.761(2) 1.0651(18) 0.044(9) Uiso 1 1 d . . . . .
H24 H 0.473(2) 0.765(2) 0.4846(17) 0.027(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.389(3) . ?
C1 C2 1.393(3) . ?
C1 C7 1.516(3) . ?
C2 C3 1.392(3) . ?
C2 C8 1.496(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11 1.520(3) . ?
C7 C21 1.525(3) . ?
C7 H7 0.9800 . ?
C8 O22 1.426(2) . ?
C8 O12 1.428(2) . ?
C8 H8 0.9800 . ?
C11 C12 1.395(3) . ?
C11 C16 1.396(3) . ?
C12 O12 1.385(2) . ?
C12 C13 1.386(3) . ?
C13 C14 1.381(3) . ?
C13 H13 0.9300 . ?
C14 O14 1.365(3) . ?
C14 C15 1.394(3) . ?
O14 H14 0.84(3) . ?
C15 C16 1.380(3) . ?
C15 Cl15 1.749(2) . ?
C16 H16 0.9300 . ?
C21 C22 1.393(3) . ?
C21 C26 1.396(3) . ?
O22 C22 1.381(2) . ?
C22 C23 1.396(3) . ?
C23 C24 1.386(3) . ?
C23 H23 0.9300 . ?
C24 O24 1.364(2) . ?
C24 C25 1.390(3) . ?
O24 H24 0.82(2) . ?
C25 C26 1.381(3) . ?
C25 Cl25 1.742(2) . ?
C26 H26 0.9300 . ?
C31 C32 1.501(3) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 O33 1.427(3) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
O33 C34 1.444(3) . ?
C34 C35 1.493(3) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?

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 119.3(2) . . ?
C6 C1 C7 122.3(2) . . ?
C2 C1 C7 118.37(19) . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 C8 118.70(19) . . ?
C1 C2 C8 121.35(19) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C1 C7 C11 110.76(17) . . ?
C1 C7 C21 111.69(17) . . ?
C11 C7 C21 114.44(17) . . ?
C1 C7 H7 106.5 . . ?
C11 C7 H7 106.5 . . ?
C21 C7 H7 106.5 . . ?
O22 C8 O12 109.89(16) . . ?
O22 C8 C2 116.06(17) . . ?
O12 C8 C2 115.21(17) . . ?
O22 C8 H8 104.8 . . ?
O12 C8 H8 104.8 . . ?
C2 C8 H8 104.8 . . ?
C12 C11 C16 116.67(19) . . ?
C12 C11 C7 124.94(19) . . ?
C16 C11 C7 118.33(19) . . ?
O12 C12 C13 112.66(19) . . ?
O12 C12 C11 126.11(19) . . ?
C13 C12 C11 121.2(2) . . ?
C12 O12 C8 124.49(16) . . ?
C14 C13 C12 121.5(2) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
O14 C14 C13 122.9(2) . . ?
O14 C14 C15 119.2(2) . . ?
C13 C14 C15 117.9(2) . . ?
C14 O14 H14 109.3(19) . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 Cl15 119.84(17) . . ?
C14 C15 Cl15 119.71(17) . . ?
C15 C16 C11 122.2(2) . . ?
C15 C16 H16 118.9 . . ?
C11 C16 H16 118.9 . . ?
C22 C21 C26 117.22(19) . . ?
C22 C21 C7 124.30(19) . . ?
C26 C21 C7 118.45(18) . . ?
C22 O22 C8 124.90(16) . . ?
O22 C22 C21 126.60(19) . . ?
O22 C22 C23 112.39(18) . . ?
C21 C22 C23 121.0(2) . . ?
C24 C23 C22 120.8(2) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
O24 C24 C23 123.0(2) . . ?
O24 C24 C25 118.45(19) . . ?
C23 C24 C25 118.59(19) . . ?
C24 O24 H24 110.6(17) . . ?
C26 C25 C24 120.3(2) . . ?
C26 C25 Cl25 120.48(17) . . ?
C24 C25 Cl25 119.17(17) . . ?
C25 C26 C21 122.0(2) . . ?
C25 C26 H26 119.0 . . ?
C21 C26 H26 119.0 . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C32 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O33 C32 C31 111.88(19) . . ?
O33 C32 H32A 109.2 . . ?
C31 C32 H32A 109.2 . . ?
O33 C32 H32B 109.2 . . ?
C31 C32 H32B 109.2 . . ?
H32A C32 H32B 107.9 . . ?
C32 O33 C34 114.71(18) . . ?
O33 C34 C35 110.8(2) . . ?
O33 C34 H34A 109.5 . . ?
C35 C34 H34A 109.5 . . ?
O33 C34 H34B 109.5 . . ?
C35 C34 H34B 109.5 . . ?
H34A C34 H34B 108.1 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 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 0.2(3) . . . . ?
C7 C1 C2 C3 -177.91(18) . . . . ?
C6 C1 C2 C8 179.02(19) . . . . ?
C7 C1 C2 C8 0.9(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C8 C2 C3 C4 -179.0(2) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C7 C1 C6 C5 178.2(2) . . . . ?
C6 C1 C7 C11 -113.9(2) . . . . ?
C2 C1 C7 C11 64.2(2) . . . . ?
C6 C1 C7 C21 117.3(2) . . . . ?
C2 C1 C7 C21 -64.7(2) . . . . ?
C3 C2 C8 O22 -117.0(2) . . . . ?
C1 C2 C8 O22 64.2(3) . . . . ?
C3 C2 C8 O12 112.6(2) . . . . ?
C1 C2 C8 O12 -66.2(3) . . . . ?
C1 C7 C11 C12 -52.3(3) . . . . ?
C21 C7 C11 C12 75.1(3) . . . . ?
C1 C7 C11 C16 124.6(2) . . . . ?
C21 C7 C11 C16 -108.1(2) . . . . ?
C16 C11 C12 O12 177.12(19) . . . . ?
C7 C11 C12 O12 -6.0(3) . . . . ?
C16 C11 C12 C13 -1.2(3) . . . . ?
C7 C11 C12 C13 175.7(2) . . . . ?
C13 C12 O12 C8 -170.80(18) . . . . ?
C11 C12 O12 C8 10.8(3) . . . . ?
O22 C8 O12 C12 -88.0(2) . . . . ?
C2 C8 O12 C12 45.4(3) . . . . ?
O12 C12 C13 C14 -178.23(18) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 O14 -178.94(19) . . . . ?
C12 C13 C14 C15 1.6(3) . . . . ?
O14 C14 C15 C16 177.97(19) . . . . ?
C13 C14 C15 C16 -2.5(3) . . . . ?
O14 C14 C15 Cl15 -0.8(3) . . . . ?
C13 C14 C15 Cl15 178.66(16) . . . . ?
C14 C15 C16 C11 1.7(3) . . . . ?
Cl15 C15 C16 C11 -179.53(16) . . . . ?
C12 C11 C16 C15 0.2(3) . . . . ?
C7 C11 C16 C15 -176.91(19) . . . . ?
C1 C7 C21 C22 52.7(3) . . . . ?
C11 C7 C21 C22 -74.1(3) . . . . ?
C1 C7 C21 C26 -125.2(2) . . . . ?
C11 C7 C21 C26 107.9(2) . . . . ?
O12 C8 O22 C22 86.4(2) . . . . ?
C2 C8 O22 C22 -46.5(3) . . . . ?
C8 O22 C22 C21 -7.8(3) . . . . ?
C8 O22 C22 C23 173.03(18) . . . . ?
C26 C21 C22 O22 -178.37(19) . . . . ?
C7 C21 C22 O22 3.6(3) . . . . ?
C26 C21 C22 C23 0.8(3) . . . . ?
C7 C21 C22 C23 -177.20(19) . . . . ?
O22 C22 C23 C24 178.84(19) . . . . ?
C21 C22 C23 C24 -0.4(3) . . . . ?
C22 C23 C24 O24 -179.7(2) . . . . ?
C22 C23 C24 C25 -0.7(3) . . . . ?
O24 C24 C25 C26 -179.56(19) . . . . ?
C23 C24 C25 C26 1.4(3) . . . . ?
O24 C24 C25 Cl25 -0.5(3) . . . . ?
C23 C24 C25 Cl25 -179.60(16) . . . . ?
C24 C25 C26 C21 -1.0(3) . . . . ?
Cl25 C25 C26 C21 179.97(16) . . . . ?
C22 C21 C26 C25 -0.1(3) . . . . ?
C7 C21 C26 C25 178.03(19) . . . . ?
C31 C32 O33 C34 -81.9(2) . . . . ?
C32 O33 C34 C35 -94.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O24 H24 O33 0.82(2) 1.80(2) 2.606(2) 170(2) .
O14 H14 O24 0.84(3) 2.04(3) 2.816(2) 153(3) 4_576
O14 H14 Cl25 0.84(3) 2.96(3) 3.6252(18) 138(2) 4_576

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.050

