# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_CrystalClear
_database_code_depnum_ccdc_archive 'CCDC 1520624'
_audit_update_record             
;
2016-12-04 deposited with the CCDC.
2018-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            
'ethyl (R)-6-methoxy-2-oxo-4-(1-tosyl-1H-indol-2-yl)-3,4-dihydro-2H-naphtho[2,1-e][1,3]oxazine-4-carboxylate'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H27 Cl3 N2 O7 S'
_chemical_formula_weight         689.96

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   10.664(3)
_cell_length_b                   10.372(2)
_cell_length_c                   14.789(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.778(6)
_cell_angle_gamma                90
_cell_volume                     1581.7(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5627
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.50

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   0.854
_exptl_transmission_factor_max   1.000
_exptl_crystal_size_max          0.750
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.407
_shelx_estimated_absorpt_T_min   0.750
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Rigaku CrystalClear'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PILATUS 200K area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13598
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.025
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             6894
_reflns_number_gt                6403
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_max     0.902
_reflns_Friedel_fraction_full    0.928

_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       'Rigaku CrystalClear'
_computing_cell_refinement       'Rigaku CrystalClear'
_computing_data_reduction        'Rigaku CrystalClear'
_computing_structure_solution    'Rigaku CrystalStructure'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Rigaku CrystalStructure'
_computing_publication_material  'Rigaku CrystalStructure'
_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)+(0.0476P)²+0.3226P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2750 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(16)
_chemical_absolute_configuration (R)
_refine_ls_number_reflns         6894
_refine_ls_number_parameters     469
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0814
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
S1 S 0.22386(6) 1.03073(6) 0.49722(4) 0.01801(12) Uani 1 1 d . . . . .
O2 O 0.62713(19) 0.91522(17) 0.80374(12) 0.0241(4) Uani 1 1 d . . . . .
O7 O 0.34441(17) 0.99752(18) 0.47725(12) 0.0231(4) Uani 1 1 d . . . . .
N1 N 0.5218(2) 0.93995(19) 0.64758(15) 0.0177(4) Uani 1 1 d . . . . .
H1 H 0.484(3) 0.903(3) 0.601(2) 0.017(7) Uiso 1 1 d . . . . .
O6 O 0.13575(18) 0.93075(19) 0.50578(13) 0.0290(4) Uani 1 1 d . . . . .
C13 C 0.5607(2) 0.8612(2) 0.72144(17) 0.0205(5) Uani 1 1 d . . . . .
C5 C 0.8021(2) 1.2102(2) 0.89778(16) 0.0179(5) Uani 1 1 d . . . . .
C3 C 0.6621(2) 1.2575(2) 0.74335(16) 0.0160(4) Uani 1 1 d . . . . .
C2 C 0.6212(2) 1.1263(2) 0.73485(16) 0.0154(4) Uani 1 1 d . . . . .
C4 C 0.7480(2) 1.2983(2) 0.82356(16) 0.0166(4) Uani 1 1 d . . . . .
C1 C 0.5164(2) 1.0805(2) 0.65043(16) 0.0150(4) Uani 1 1 d . . . . .
C25 C 0.1402(2) 1.1439(3) 0.41530(16) 0.0196(5) Uani 1 1 d . . . . .
C11 C 0.6685(2) 1.0423(2) 0.80574(16) 0.0172(4) Uani 1 1 d . . . . .
C9 C 0.8138(3) 0.9921(3) 0.96245(18) 0.0246(5) Uani 1 1 d . . . . .
C8 C 0.9038(3) 1.0334(3) 1.04068(17) 0.0288(5) Uani 1 1 d . . . . .
C30 C 0.1994(2) 1.2598(3) 0.40264(18) 0.0226(5) Uani 1 1 d . . . . .
C26 C 0.0165(2) 1.1130(3) 0.36216(18) 0.0245(5) Uani 1 1 d . . . . .
H26 H -0.026(3) 1.037(4) 0.373(2) 0.034(8) Uiso 1 1 d . . . . .
C14 C 0.5483(2) 1.1381(2) 0.56228(16) 0.0167(4) Uani 1 1 d . . . . .
C7 C 0.9457(3) 1.1621(3) 1.04865(19) 0.0282(6) Uani 1 1 d . . . . .
C6 C 0.8949(2) 1.2495(3) 0.97991(17) 0.0231(5) Uani 1 1 d . . . . .
C18 C 0.3682(2) 1.1913(2) 0.73875(17) 0.0187(5) Uani 1 1 d . . . . .
H18 H 0.435(3) 1.212(3) 0.793(2) 0.015(7) Uiso 1 1 d . . . . .
C22 C -0.0352(3) 1.2259(3) 0.6615(2) 0.0274(6) Uani 1 1 d . . . . .
H22 H -0.132(3) 1.233(3) 0.640(2) 0.027(8) Uiso 1 1 d . . . . .
C10 C 0.7618(2) 1.0801(2) 0.88888(16) 0.0186(5) Uani 1 1 d . . . . .
C24 C 0.1682(2) 1.1637(2) 0.63858(17) 0.0179(5) Uani 1 1 d . . . . .
C20 C 0.1604(3) 1.2747(3) 0.78053(19) 0.0236(5) Uani 1 1 d . . . . .
H20 H 0.208(3) 1.308(3) 0.837(3) 0.039(9) Uiso 1 1 d . . . . .
C19 C 0.2319(2) 1.2148(2) 0.72541(16) 0.0182(5) Uani 1 1 d . . . . .
C21 C 0.0273(3) 1.2801(3) 0.7479(2) 0.0262(6) Uani 1 1 d . . . . .
H21 H -0.022(3) 1.316(3) 0.780(2) 0.034(9) Uiso 1 1 d . . . . .
C23 C 0.0333(2) 1.1670(3) 0.60494(19) 0.0257(6) Uani 1 1 d . . . . .
H23 H -0.010(3) 1.131(3) 0.548(2) 0.033(8) Uiso 1 1 d . . . . .
N2 N 0.26349(19) 1.1118(2) 0.59776(14) 0.0183(4) Uani 1 1 d . . . . .
C17 C 0.3869(2) 1.1297(2) 0.66213(15) 0.0159(4) Uani 1 1 d . . . . .
O1 O 0.79173(17) 1.42173(16) 0.83997(12) 0.0215(4) Uani 1 1 d . . . . .
O5 O 0.63083(16) 1.06352(16) 0.53311(11) 0.0204(4) Uani 1 1 d . . . . .
O3 O 0.5432(2) 0.74622(18) 0.72047(14) 0.0319(5) Uani 1 1 d . . . . .
O4 O 0.50758(16) 1.24124(16) 0.53005(11) 0.0194(3) Uani 1 1 d . . . . .
C15 C 0.6648(3) 1.1052(3) 0.44781(18) 0.0242(5) Uani 1 1 d . . . . .
H15 H 0.7322 1.1732 0.4625 0.029 Uiso 1 1 calc R U . . .
H15A H 0.5876 1.1404 0.4025 0.029 Uiso 1 1 calc R U . . .
C29 C 0.1315(3) 1.3467(3) 0.3371(2) 0.0280(6) Uani 1 1 d . . . . .
H29 H 0.169(4) 1.430(4) 0.325(3) 0.044(10) Uiso 1 1 d . . . . .
C28 C 0.0060(3) 1.3189(3) 0.28316(18) 0.0274(6) Uani 1 1 d . . . . .
C27 C -0.0490(3) 1.2016(3) 0.2958(2) 0.0296(6) Uani 1 1 d . . . . .
C16 C 0.7148(3) 0.9896(3) 0.4077(2) 0.0319(6) Uani 1 1 d . . . . .
H16 H 0.6506 0.9201 0.3990 0.048 Uiso 1 1 calc R U . . .
H16A H 0.7960 0.9608 0.4505 0.048 Uiso 1 1 calc R U . . .
H16B H 0.7305 1.0120 0.3471 0.048 Uiso 1 1 calc R U . . .
C12 C 0.7368(3) 1.5150(3) 0.7701(2) 0.0327(6) Uani 1 1 d . . . . .
H12 H 0.6425 1.5175 0.7612 0.049 Uiso 1 1 calc R U . . .
H12A H 0.7566 1.4914 0.7111 0.049 Uiso 1 1 calc R U . . .
H12B H 0.7734 1.6001 0.7901 0.049 Uiso 1 1 calc R U . . .
C31 C -0.0666(3) 1.4158(3) 0.2125(2) 0.0411(8) Uani 1 1 d . . . . .
H31 H -0.1001 1.4849 0.2450 0.062 Uiso 1 1 calc R U . . .
H31A H -0.1389 1.3728 0.1686 0.062 Uiso 1 1 calc R U . . .
H31B H -0.0077 1.4525 0.1781 0.062 Uiso 1 1 calc R U . . .
Cl3 Cl 0.65470(15) 1.60539(16) 1.00457(9) 0.0937(5) Uani 1 1 d . . . . .
Cl1 Cl 0.41687(18) 1.74769(18) 0.95169(15) 0.1146(6) Uani 1 1 d . . . . .
Cl2 Cl 0.43332(15) 1.50053(13) 0.87070(9) 0.0861(4) Uani 1 1 d . . . . .
C32 C 0.5171(4) 1.6414(3) 0.9143(2) 0.0447(8) Uani 1 1 d . . . . .
H32 H 0.5466 1.6832 0.8624 0.054 Uiso 1 1 calc R U . . .
H32A H 0.287(3) 1.280(3) 0.4392(18) 0.012(6) Uiso 1 1 d . . . . .
H32B H -0.131(4) 1.181(4) 0.259(3) 0.040(10) Uiso 1 1 d . . . . .
H32C H 0.925(3) 1.336(3) 0.985(2) 0.026(8) Uiso 1 1 d . . . . .
H32D H 0.624(3) 1.313(3) 0.696(2) 0.017(7) Uiso 1 1 d . . . . .
H32E H 1.006(3) 1.189(3) 1.100(2) 0.031(8) Uiso 1 1 d . . . . .
H32F H 0.933(3) 0.973(3) 1.088(2) 0.033(8) Uiso 1 1 d . . . . .
H32G H 0.780(3) 0.905(4) 0.959(2) 0.036(9) 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
S1 O6 1.426(2) . ?
S1 O7 1.4326(19) . ?
S1 N2 1.666(2) . ?
S1 C25 1.758(3) . ?
O2 C13 1.363(3) . ?
O2 C11 1.388(3) . ?
N1 C13 1.342(3) . ?
N1 C1 1.460(3) . ?
C13 O3 1.207(3) . ?
C5 C10 1.412(4) . ?
C5 C6 1.417(3) . ?
C5 C4 1.431(3) . ?
C3 C4 1.368(3) . ?
C3 C2 1.424(3) . ?
C2 C11 1.357(3) . ?
C2 C1 1.523(3) . ?
C4 O1 1.363(3) . ?
C1 C17 1.523(3) . ?
C1 C14 1.548(3) . ?
C25 C26 1.390(4) . ?
C25 C30 1.392(4) . ?
C11 C10 1.425(3) . ?
C9 C8 1.370(4) . ?
C9 C10 1.420(3) . ?
C8 C7 1.403(4) . ?
C30 C29 1.385(4) . ?
C26 C27 1.395(4) . ?
C14 O4 1.206(3) . ?
C14 O5 1.324(3) . ?
C7 C6 1.366(4) . ?
C18 C17 1.360(3) . ?
C18 C19 1.436(3) . ?
C22 C23 1.384(4) . ?
C22 C21 1.399(4) . ?
C24 C19 1.395(3) . ?
C24 C23 1.398(3) . ?
C24 N2 1.414(3) . ?
C20 C21 1.378(4) . ?
C20 C19 1.396(3) . ?
N2 C17 1.426(3) . ?
O1 C12 1.427(3) . ?
O5 C15 1.464(3) . ?
C15 C16 1.496(4) . ?
C29 C28 1.402(4) . ?
C28 C27 1.384(4) . ?
C28 C31 1.513(4) . ?
Cl3 C32 1.753(4) . ?
Cl1 C32 1.722(4) . ?
Cl2 C32 1.748(4) . ?

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
O6 S1 O7 119.31(12) . . ?
O6 S1 N2 108.10(11) . . ?
O7 S1 N2 105.59(10) . . ?
O6 S1 C25 108.45(12) . . ?
O7 S1 C25 110.06(11) . . ?
N2 S1 C25 104.26(11) . . ?
C13 O2 C11 119.96(19) . . ?
C13 N1 C1 126.2(2) . . ?
O3 C13 N1 125.2(2) . . ?
O3 C13 O2 117.4(2) . . ?
N1 C13 O2 117.3(2) . . ?
C10 C5 C6 119.0(2) . . ?
C10 C5 C4 119.0(2) . . ?
C6 C5 C4 122.0(2) . . ?
C4 C3 C2 119.6(2) . . ?
C11 C2 C3 120.0(2) . . ?
C11 C2 C1 118.9(2) . . ?
C3 C2 C1 120.9(2) . . ?
O1 C4 C3 124.6(2) . . ?
O1 C4 C5 114.2(2) . . ?
C3 C4 C5 121.2(2) . . ?
N1 C1 C17 112.4(2) . . ?
N1 C1 C2 107.98(19) . . ?
C17 C1 C2 107.43(18) . . ?
N1 C1 C14 110.01(19) . . ?
C17 C1 C14 111.51(18) . . ?
C2 C1 C14 107.29(19) . . ?
C26 C25 C30 121.4(2) . . ?
C26 C25 S1 118.5(2) . . ?
C30 C25 S1 120.07(18) . . ?
C2 C11 O2 122.6(2) . . ?
C2 C11 C10 122.0(2) . . ?
O2 C11 C10 115.3(2) . . ?
C8 C9 C10 119.9(3) . . ?
C9 C8 C7 120.5(3) . . ?
C29 C30 C25 118.8(2) . . ?
C25 C26 C27 118.5(3) . . ?
O4 C14 O5 126.3(2) . . ?
O4 C14 C1 122.7(2) . . ?
O5 C14 C1 110.84(19) . . ?
C6 C7 C8 120.8(3) . . ?
C7 C6 C5 120.3(3) . . ?
C17 C18 C19 108.9(2) . . ?
C23 C22 C21 121.8(3) . . ?
C5 C10 C9 119.5(2) . . ?
C5 C10 C11 118.2(2) . . ?
C9 C10 C11 122.3(2) . . ?
C19 C24 C23 122.2(2) . . ?
C19 C24 N2 107.7(2) . . ?
C23 C24 N2 130.1(2) . . ?
C21 C20 C19 118.7(2) . . ?
C24 C19 C20 119.7(2) . . ?
C24 C19 C18 107.4(2) . . ?
C20 C19 C18 132.8(2) . . ?
C20 C21 C22 120.8(3) . . ?
C22 C23 C24 116.7(2) . . ?
C24 N2 C17 107.88(18) . . ?
C24 N2 S1 121.78(16) . . ?
C17 N2 S1 129.94(16) . . ?
C18 C17 N2 108.1(2) . . ?
C18 C17 C1 125.6(2) . . ?
N2 C17 C1 126.2(2) . . ?
C4 O1 C12 116.68(19) . . ?
C14 O5 C15 116.07(18) . . ?
O5 C15 C16 107.3(2) . . ?
C30 C29 C28 121.2(3) . . ?
C27 C28 C29 118.7(3) . . ?
C27 C28 C31 121.2(3) . . ?
C29 C28 C31 120.2(3) . . ?
C28 C27 C26 121.4(3) . . ?
Cl1 C32 Cl2 110.7(2) . . ?
Cl1 C32 Cl3 111.1(2) . . ?
Cl2 C32 Cl3 110.7(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
C1 N1 C13 O3 166.0(3) . . . . ?
C1 N1 C13 O2 -15.2(4) . . . . ?
C11 O2 C13 O3 169.5(2) . . . . ?
C11 O2 C13 N1 -9.4(3) . . . . ?
C4 C3 C2 C11 -0.6(3) . . . . ?
C4 C3 C2 C1 174.3(2) . . . . ?
C2 C3 C4 O1 -178.7(2) . . . . ?
C2 C3 C4 C5 2.7(3) . . . . ?
C10 C5 C4 O1 178.9(2) . . . . ?
C6 C5 C4 O1 -1.1(3) . . . . ?
C10 C5 C4 C3 -2.4(3) . . . . ?
C6 C5 C4 C3 177.6(2) . . . . ?
C13 N1 C1 C17 -89.0(3) . . . . ?
C13 N1 C1 C2 29.3(3) . . . . ?
C13 N1 C1 C14 146.1(2) . . . . ?
C11 C2 C1 N1 -21.0(3) . . . . ?
C3 C2 C1 N1 164.0(2) . . . . ?
C11 C2 C1 C17 100.4(2) . . . . ?
C3 C2 C1 C17 -74.5(3) . . . . ?
C11 C2 C1 C14 -139.5(2) . . . . ?
C3 C2 C1 C14 45.5(3) . . . . ?
O6 S1 C25 C26 -10.3(2) . . . . ?
O7 S1 C25 C26 121.9(2) . . . . ?
N2 S1 C25 C26 -125.3(2) . . . . ?
O6 S1 C25 C30 171.79(19) . . . . ?
O7 S1 C25 C30 -56.0(2) . . . . ?
N2 S1 C25 C30 56.8(2) . . . . ?
C3 C2 C11 O2 176.3(2) . . . . ?
C1 C2 C11 O2 1.3(3) . . . . ?
C3 C2 C11 C10 -1.8(3) . . . . ?
C1 C2 C11 C10 -176.8(2) . . . . ?
C13 O2 C11 C2 15.9(3) . . . . ?
C13 O2 C11 C10 -165.9(2) . . . . ?
C10 C9 C8 C7 -0.2(4) . . . . ?
C26 C25 C30 C29 1.6(4) . . . . ?
S1 C25 C30 C29 179.5(2) . . . . ?
C30 C25 C26 C27 -0.8(4) . . . . ?
S1 C25 C26 C27 -178.7(2) . . . . ?
N1 C1 C14 O4 152.6(2) . . . . ?
C17 C1 C14 O4 27.3(3) . . . . ?
C2 C1 C14 O4 -90.1(3) . . . . ?
N1 C1 C14 O5 -31.5(3) . . . . ?
C17 C1 C14 O5 -156.88(19) . . . . ?
C2 C1 C14 O5 85.7(2) . . . . ?
C9 C8 C7 C6 1.8(4) . . . . ?
C8 C7 C6 C5 -2.2(4) . . . . ?
C10 C5 C6 C7 1.0(4) . . . . ?
C4 C5 C6 C7 -179.1(2) . . . . ?
C6 C5 C10 C9 0.6(3) . . . . ?
C4 C5 C10 C9 -179.3(2) . . . . ?
C6 C5 C10 C11 -180.0(2) . . . . ?
C4 C5 C10 C11 0.1(3) . . . . ?
C8 C9 C10 C5 -1.0(4) . . . . ?
C8 C9 C10 C11 179.6(2) . . . . ?
C2 C11 C10 C5 2.0(3) . . . . ?
O2 C11 C10 C5 -176.2(2) . . . . ?
C2 C11 C10 C9 -178.6(2) . . . . ?
O2 C11 C10 C9 3.1(3) . . . . ?
C23 C24 C19 C20 -1.7(4) . . . . ?
N2 C24 C19 C20 178.9(2) . . . . ?
C23 C24 C19 C18 178.2(2) . . . . ?
N2 C24 C19 C18 -1.3(3) . . . . ?
C21 C20 C19 C24 0.8(4) . . . . ?
C21 C20 C19 C18 -178.9(3) . . . . ?
C17 C18 C19 C24 0.9(3) . . . . ?
C17 C18 C19 C20 -179.3(3) . . . . ?
C19 C20 C21 C22 0.5(4) . . . . ?
C23 C22 C21 C20 -1.1(4) . . . . ?
C21 C22 C23 C24 0.3(4) . . . . ?
C19 C24 C23 C22 1.0(4) . . . . ?
N2 C24 C23 C22 -179.7(2) . . . . ?
C19 C24 N2 C17 1.2(3) . . . . ?
C23 C24 N2 C17 -178.2(3) . . . . ?
C19 C24 N2 S1 174.71(17) . . . . ?
C23 C24 N2 S1 -4.7(4) . . . . ?
O6 S1 N2 C24 -53.0(2) . . . . ?
O7 S1 N2 C24 178.27(18) . . . . ?
C25 S1 N2 C24 62.3(2) . . . . ?
O6 S1 N2 C17 118.9(2) . . . . ?
O7 S1 N2 C17 -9.8(2) . . . . ?
C25 S1 N2 C17 -125.8(2) . . . . ?
C19 C18 C17 N2 -0.1(3) . . . . ?
C19 C18 C17 C1 -176.3(2) . . . . ?
C24 N2 C17 C18 -0.7(3) . . . . ?
S1 N2 C17 C18 -173.46(19) . . . . ?
C24 N2 C17 C1 175.5(2) . . . . ?
S1 N2 C17 C1 2.7(4) . . . . ?
N1 C1 C17 C18 112.4(3) . . . . ?
C2 C1 C17 C18 -6.2(3) . . . . ?
C14 C1 C17 C18 -123.5(3) . . . . ?
N1 C1 C17 N2 -63.1(3) . . . . ?
C2 C1 C17 N2 178.2(2) . . . . ?
C14 C1 C17 N2 60.9(3) . . . . ?
C3 C4 O1 C12 4.0(3) . . . . ?
C5 C4 O1 C12 -177.3(2) . . . . ?
O4 C14 O5 C15 -6.6(3) . . . . ?
C1 C14 O5 C15 177.7(2) . . . . ?
C14 O5 C15 C16 -159.1(2) . . . . ?
C25 C30 C29 C28 -0.9(4) . . . . ?
C30 C29 C28 C27 -0.6(4) . . . . ?
C30 C29 C28 C31 179.6(3) . . . . ?
C29 C28 C27 C26 1.5(4) . . . . ?
C31 C28 C27 C26 -178.7(3) . . . . ?
C25 C26 C27 C28 -0.8(4) . . . . ?

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.044

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_CrystalClear_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1834631'
_audit_update_record             
;
2018-04-04 deposited with the CCDC.
2018-06-25 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            
'Methyl (S)-(1-(3-bromophenyl)-2-hydroxy-1-(5-methoxyfuran-2-yl)ethyl)carbamate'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 Br N O5'
_chemical_formula_weight         370.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   5.8577(16)
_cell_length_b                   14.389(4)
_cell_length_c                   9.621(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.654(6)
_cell_angle_gamma                90
_cell_volume                     808.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    3310
_cell_measurement_theta_min      3.767
_cell_measurement_theta_max      27.486

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   0.854
_exptl_transmission_factor_max   1.000
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    2.565
_shelx_estimated_absorpt_T_min   0.467
_shelx_estimated_absorpt_T_max   0.566
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Rigaku CrystalClear'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PILATUS 200K area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6877
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.490
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_point_group_measured_fraction_full 0.883
_reflns_number_total             3178
_reflns_number_gt                2589
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.670
_reflns_Friedel_fraction_max     0.713
_reflns_Friedel_fraction_full    0.768

_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       'Rigaku CrystalClear'
_computing_cell_refinement       'Rigaku CrystalClear'
_computing_data_reduction        'Rigaku CrystalClear'
_computing_structure_solution    'Rigaku CrystalStructure'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Rigaku CrystalStructure'
_computing_publication_material  'Rigaku CrystalStructure'
_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)+(0.0169P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 951 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(5)
_chemical_absolute_configuration (S)
_refine_ls_number_reflns         3178
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_ref         0.0508
_refine_ls_wR_factor_gt          0.0504
_refine_ls_goodness_of_fit_ref   0.826
_refine_ls_restrained_S_all      0.826
_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
Br1 Br 0.42236(8) 0.84349(3) 1.36989(4) 0.04389(14) Uani 1 1 d . . . . .
O2 O 0.6047(4) 0.49737(17) 1.1642(3) 0.0249(6) Uani 1 1 d . . . . .
O4 O 0.2399(4) 0.59513(16) 0.7136(2) 0.0216(6) Uani 1 1 d . . . . .
N1 N 0.3380(5) 0.56412(19) 1.0066(3) 0.0148(6) Uani 1 1 d . . . . .
H1A H 0.208(6) 0.563(2) 0.983(4) 0.016(11) Uiso 1 1 d . . . . .
O1 O 0.8622(4) 0.53959(17) 0.9574(3) 0.0238(6) Uani 1 1 d . . . . .
H1 H 0.813(6) 0.530(3) 1.020(4) 0.019(12) Uiso 1 1 d . . . . .
O3 O 0.2242(4) 0.48902(16) 1.1879(2) 0.0239(6) Uani 1 1 d . . . . .
C3 C 0.4785(6) 0.7337(2) 1.1311(3) 0.0161(7) Uani 1 1 d . . . . .
H3 H 0.3435 0.7036 1.1562 0.019 Uiso 1 1 calc R U . . .
C13 C 0.1145(6) 0.7347(3) 0.6391(4) 0.0224(8) Uani 1 1 d . . . . .
H13 H 0.040(5) 0.779(2) 0.575(3) 0.020(9) Uiso 1 1 d . . . . .
C11 C 0.3327(6) 0.6617(2) 0.8067(3) 0.0152(8) Uani 1 1 d . . . . .
C4 C 0.5684(6) 0.8079(2) 1.2095(3) 0.0233(8) Uani 1 1 d . . . . .
C1 C 0.4865(5) 0.6226(2) 0.9260(3) 0.0132(7) Uani 1 1 d . . . . .
C9 C 0.4049(6) 0.5156(2) 1.1207(3) 0.0169(7) Uani 1 1 d . . . . .
C8 C 0.6747(5) 0.5650(2) 0.8624(3) 0.0183(7) Uani 1 1 d . . . . .
H8 H 0.6042 0.5076 0.8215 0.022 Uiso 1 1 calc R U . . .
H8A H 0.7338 0.6011 0.7855 0.022 Uiso 1 1 calc R U . . .
C7 C 0.7816(5) 0.7509(2) 0.9799(4) 0.0192(7) Uani 1 1 d . . . . .
H7 H 0.8560 0.7318 0.9006 0.023 Uiso 1 1 calc R U . . .
C14 C 0.2619(6) 0.7464(3) 0.7653(3) 0.0186(8) Uani 1 1 d . . . . .
H14 H 0.289(5) 0.803(2) 0.814(3) 0.023(10) Uiso 1 1 d . . . . .
C2 C 0.5858(5) 0.7036(2) 1.0160(3) 0.0133(7) Uani 1 1 d . . . . .
O5 O 0.0117(7) 0.5869(3) 0.5164(3) 0.0417(7) Uani 1 1 d . . . . .
C5 C 0.7646(6) 0.8546(3) 1.1759(3) 0.0255(9) Uani 1 1 d . . . . .
H5 H 0.8258 0.9047 1.2313 0.031 Uiso 1 1 calc R U . . .
C12 C 0.1094(6) 0.6434(3) 0.6140(3) 0.0238(9) Uani 1 1 d . . . . .
C6 C 0.8673(6) 0.8254(3) 1.0592(4) 0.0261(9) Uani 1 1 d . . . . .
H6 H 0.9994 0.8571 1.0328 0.031 Uiso 1 1 calc R U . . .
C10 C 0.2743(7) 0.4360(3) 1.3145(4) 0.0355(10) Uani 1 1 d . . . . .
H10 H 0.3922 0.4680 1.3747 0.053 Uiso 1 1 calc R U . . .
H10A H 0.3297 0.3741 1.2910 0.053 Uiso 1 1 calc R U . . .
H10B H 0.1348 0.4298 1.3636 0.053 Uiso 1 1 calc R U . . .
C15 C -0.1298(8) 0.6353(4) 0.4110(4) 0.0545(14) Uani 1 1 d . . . . .
H15 H -0.0370 0.6807 0.3648 0.082 Uiso 1 1 calc R U . . .
H15A H -0.2535 0.6674 0.4542 0.082 Uiso 1 1 calc R U . . .
H15B H -0.1956 0.5906 0.3420 0.082 Uiso 1 1 calc R U . . .


_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
Br1 C4 1.894(3) . ?
O2 C9 1.239(4) . ?
O4 C12 1.366(4) . ?
O4 C11 1.392(4) . ?
N1 C9 1.333(4) . ?
N1 C1 1.475(4) . ?
O1 C8 1.419(4) . ?
O3 C9 1.340(4) . ?
O3 C10 1.447(4) . ?
C3 C4 1.386(4) . ?
C3 C2 1.387(4) . ?
C13 C12 1.336(5) . ?
C13 C14 1.442(5) . ?
C11 C14 1.337(5) . ?
C11 C1 1.509(5) . ?
C4 C5 1.391(5) . ?
C1 C2 1.537(4) . ?
C1 C8 1.545(4) . ?
C7 C6 1.386(5) . ?
C7 C2 1.401(4) . ?
O5 C12 1.335(5) . ?
O5 C15 1.436(5) . ?
C5 C6 1.381(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O4 C11 105.6(3) . . ?
C9 N1 C1 125.8(3) . . ?
C9 O3 C10 116.3(3) . . ?
C4 C3 C2 119.9(3) . . ?
C12 C13 C14 105.7(3) . . ?
C14 C11 O4 109.9(3) . . ?
C14 C11 C1 135.9(3) . . ?
O4 C11 C1 114.2(3) . . ?
C3 C4 C5 122.0(3) . . ?
C3 C4 Br1 118.3(3) . . ?
C5 C4 Br1 119.7(3) . . ?
N1 C1 C11 105.7(3) . . ?
N1 C1 C2 110.4(2) . . ?
C11 C1 C2 108.7(3) . . ?
N1 C1 C8 111.8(3) . . ?
C11 C1 C8 107.5(3) . . ?
C2 C1 C8 112.4(3) . . ?
O2 C9 N1 126.6(3) . . ?
O2 C9 O3 122.5(3) . . ?
N1 C9 O3 110.9(3) . . ?
O1 C8 C1 115.0(3) . . ?
C6 C7 C2 120.5(3) . . ?
C11 C14 C13 107.2(3) . . ?
C3 C2 C7 118.6(3) . . ?
C3 C2 C1 120.8(3) . . ?
C7 C2 C1 120.6(3) . . ?
C12 O5 C15 113.1(3) . . ?
C6 C5 C4 117.7(3) . . ?
O5 C12 C13 136.7(3) . . ?
O5 C12 O4 111.6(3) . . ?
C13 C12 O4 111.7(3) . . ?
C5 C6 C7 121.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 O4 C11 C14 -0.1(4) . . . . ?
C12 O4 C11 C1 -179.5(3) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C2 C3 C4 Br1 -177.6(2) . . . . ?
C9 N1 C1 C11 179.5(3) . . . . ?
C9 N1 C1 C2 -63.1(4) . . . . ?
C9 N1 C1 C8 62.8(4) . . . . ?
C14 C11 C1 N1 116.6(4) . . . . ?
O4 C11 C1 N1 -64.2(3) . . . . ?
C14 C11 C1 C2 -2.0(5) . . . . ?
O4 C11 C1 C2 177.2(3) . . . . ?
C14 C11 C1 C8 -123.9(4) . . . . ?
O4 C11 C1 C8 55.4(4) . . . . ?
C1 N1 C9 O2 -14.1(5) . . . . ?
C1 N1 C9 O3 164.7(3) . . . . ?
C10 O3 C9 O2 -0.9(4) . . . . ?
C10 O3 C9 N1 -179.7(3) . . . . ?
N1 C1 C8 O1 -77.4(3) . . . . ?
C11 C1 C8 O1 167.0(3) . . . . ?
C2 C1 C8 O1 47.5(4) . . . . ?
O4 C11 C14 C13 0.2(4) . . . . ?
C1 C11 C14 C13 179.5(4) . . . . ?
C12 C13 C14 C11 -0.3(4) . . . . ?
C4 C3 C2 C7 -1.5(4) . . . . ?
C4 C3 C2 C1 -178.8(3) . . . . ?
C6 C7 C2 C3 0.9(4) . . . . ?
C6 C7 C2 C1 178.3(3) . . . . ?
N1 C1 C2 C3 -22.4(4) . . . . ?
C11 C1 C2 C3 93.2(3) . . . . ?
C8 C1 C2 C3 -148.0(3) . . . . ?
N1 C1 C2 C7 160.2(3) . . . . ?
C11 C1 C2 C7 -84.2(3) . . . . ?
C8 C1 C2 C7 34.6(4) . . . . ?
C3 C4 C5 C6 1.0(5) . . . . ?
Br1 C4 C5 C6 179.1(3) . . . . ?
C15 O5 C12 C13 -1.7(7) . . . . ?
C15 O5 C12 O4 179.1(4) . . . . ?
C14 C13 C12 O5 -178.9(5) . . . . ?
C14 C13 C12 O4 0.3(4) . . . . ?
C11 O4 C12 O5 179.3(3) . . . . ?
C11 O4 C12 C13 -0.1(4) . . . . ?
C4 C5 C6 C7 -1.5(5) . . . . ?
C2 C7 C6 C5 0.6(5) . . . . ?

_refine_diff_density_max         0.326
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.068

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_CrystalClear_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1520625'
_audit_update_record             
;
2016-12-04 deposited with the CCDC.
2018-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            
"(R)-3,3'-Di([1,1':3',1''-terphenyl]-5'-yl)-5,5',6,6',7,7',8,8'-octahydro-[1,1'-binaphthalene]-2,2'-diyl bis(dihydrogen phosphate) pyridinium salt"
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C67 H60 Cl2 N2 O8 P2'
_chemical_formula_weight         1154.01

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'
P P 0.1023 0.0942 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   11.4778(15)
_cell_length_b                   13.6448(18)
_cell_length_c                   36.849(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5771.0(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    15355
_cell_measurement_theta_min      3.142
_cell_measurement_theta_max      27.49

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             2416
_exptl_transmission_factor_min   0.854
_exptl_transmission_factor_max   1.000
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.228
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Rigaku CrystalClear'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PILATUS 200K area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39877
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         3.037
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.933
_reflns_number_total             12226
_reflns_number_gt                10577
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_max     0.870
_reflns_Friedel_fraction_full    0.889

_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       'Rigaku CrystalClear'
_computing_cell_refinement       'Rigaku CrystalClear'
_computing_data_reduction        'Rigaku CrystalClear'
_computing_structure_solution    'Rigaku CrystalStructure'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Rigaku CrystalStructure'
_computing_publication_material  'Rigaku CrystalStructure'
_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)+(0.0485P)²+1.7502P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 4156 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(17)
_chemical_absolute_configuration (R)
_refine_ls_number_reflns         12226
_refine_ls_number_parameters     746
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
P1 P -0.19413(6) 0.49664(5) 0.11481(2) 0.02186(15) Uani 1 1 d . . . . .
P2 P -0.17454(7) 0.75172(5) 0.06298(2) 0.02272(15) Uani 1 1 d . . . . .
Cl1 Cl 0.44639(8) 0.54629(8) 0.19679(3) 0.0480(2) Uani 1 1 d . . . . .
Cl0 Cl 0.65490(8) 0.44205(7) 0.21985(3) 0.0501(3) Uani 1 1 d . . . . .
O5 O -0.14912(17) 0.80738(14) 0.10106(5) 0.0222(4) Uani 1 1 d . . . . .
O6 O -0.16614(17) 0.54766(14) 0.15385(5) 0.0212(4) Uani 1 1 d . . . . .
O7 O -0.21994(18) 0.39073(15) 0.12237(6) 0.0283(5) Uani 1 1 d . . . . .
O8 O -0.09402(18) 0.51741(14) 0.08958(6) 0.0250(4) Uani 1 1 d . . . . .
O9 O -0.28804(17) 0.69882(15) 0.06641(6) 0.0258(4) Uani 1 1 d . . . . .
O10 O -0.1649(2) 0.82868(15) 0.03412(6) 0.0309(5) Uani 1 1 d . . . . .
O11 O -0.06826(19) 0.68148(16) 0.05864(6) 0.0287(5) Uani 1 1 d . . . . .
H48 H -0.076(4) 0.633(3) 0.0704(12) 0.052(13) Uiso 1 1 d . . . . .
C12 C -0.2257(2) 0.80395(19) 0.13060(7) 0.0197(5) Uani 1 1 d . . . . .
O13 O -0.31016(19) 0.54597(17) 0.10298(6) 0.0303(5) Uani 1 1 d . . . . .
H47 H -0.296(4) 0.592(3) 0.0897(12) 0.051(13) Uiso 1 1 d . . . . .
C14 C 0.0547(2) 0.4450(2) 0.17011(7) 0.0199(5) Uani 1 1 d . . . . .
C15 C 0.0225(2) 0.7600(2) 0.17350(8) 0.0210(6) Uani 1 1 d . . . . .
C16 C -0.1920(2) 0.75238(19) 0.16140(7) 0.0192(5) Uani 1 1 d . . . . .
C17 C -0.0276(3) 0.3809(2) 0.18477(8) 0.0218(6) Uani 1 1 d . . . . .
H1 H -0.0996 0.4058 0.1935 0.026 Uiso 1 1 calc R U . . .
C18 C 0.1596(3) 0.40661(19) 0.15666(8) 0.0214(6) Uani 1 1 d . . . . .
H2 H 0.2146 0.4498 0.1460 0.026 Uiso 1 1 calc R U . . .
C19 C -0.3309(3) 0.8562(2) 0.12948(8) 0.0224(6) Uani 1 1 d . . . . .
C20 C 0.1328(2) 0.6120(2) 0.18012(8) 0.0209(6) Uani 1 1 d . . . . .
H3 H 0.2040 0.5808 0.1863 0.025 Uiso 1 1 calc R U . . .
C21 C -0.2225(3) 0.7018(2) 0.22691(8) 0.0255(6) Uani 1 1 d . . . . .
H29 H -0.1548 0.7375 0.2370 0.031 Uiso 1 1 calc R U . . .
H30 H -0.1962 0.6349 0.2205 0.031 Uiso 1 1 calc R U . . .
C22 C 0.1855(3) 0.3068(2) 0.15854(8) 0.0226(6) Uani 1 1 d . . . . .
C23 C -0.0754(2) 0.70306(19) 0.16398(7) 0.0184(5) Uani 1 1 d . . . . .
C24 C -0.3674(2) 0.8067(2) 0.19239(8) 0.0231(6) Uani 1 1 d . . . . .
C25 C -0.2629(2) 0.7536(2) 0.19266(7) 0.0211(6) Uani 1 1 d . . . . .
N0 N 0.3216(3) 0.67090(19) 0.03385(7) 0.0312(6) Uani 1 1 d . . . . .
C27 C -0.6600(3) 0.9404(2) 0.04741(8) 0.0254(6) Uani 1 1 d . . . . .
C28 C -0.5355(2) 0.9542(2) 0.05775(8) 0.0247(6) Uani 1 1 d . . . . .
C29 C -0.3024(3) 0.9782(2) 0.07852(8) 0.0252(6) Uani 1 1 d . . . . .
H4 H -0.2231 0.9859 0.0853 0.030 Uiso 1 1 calc R U . . .
C30 C -0.4634(3) 1.0209(2) 0.03966(8) 0.0262(6) Uani 1 1 d . . . . .
H5 H -0.4941 1.0582 0.0201 0.031 Uiso 1 1 calc R U . . .
C31 C 0.1278(2) 0.7136(2) 0.18171(8) 0.0213(6) Uani 1 1 d . . . . .
C32 C -0.0047(3) 0.2801(2) 0.18670(8) 0.0231(6) Uani 1 1 d . . . . .
C33 C -0.3990(3) 0.8555(2) 0.16081(8) 0.0252(6) Uani 1 1 d . . . . .
H6 H -0.4707 0.8903 0.1606 0.030 Uiso 1 1 calc R U . . .
C34 C -0.0660(2) 0.60151(19) 0.16171(7) 0.0182(5) Uani 1 1 d . . . . .
C35 C -0.0948(3) 0.2096(2) 0.20012(8) 0.0255(6) Uani 1 1 d . . . . .
C36 C -0.4876(3) 0.9008(2) 0.08646(8) 0.0229(6) Uani 1 1 d . . . . .
H7 H -0.5354 0.8553 0.0991 0.028 Uiso 1 1 calc R U . . .
C37 C -0.2729(3) 1.1067(2) 0.03066(9) 0.0290(7) Uani 1 1 d . . . . .
C38 C 0.1013(3) 0.2452(2) 0.17394(8) 0.0244(6) Uani 1 1 d . . . . .
H8 H 0.1173 0.1770 0.1757 0.029 Uiso 1 1 calc R U . . .
C39 C 0.2990(3) 0.2680(2) 0.14436(8) 0.0259(6) Uani 1 1 d . . . . .
C40 C 0.4204(3) 0.6515(3) 0.08975(9) 0.0337(7) Uani 1 1 d . . . . .
H62 H 0.4908 0.6510 0.1033 0.040 Uiso 1 1 calc R U . . .
C41 C -0.4441(3) 0.8156(3) 0.22572(9) 0.0310(7) Uani 1 1 d . . . . .
H31 H -0.5115 0.7708 0.2231 0.037 Uiso 1 1 calc R U . . .
H32 H -0.4745 0.8833 0.2273 0.037 Uiso 1 1 calc R U . . .
N1 N -0.0664(3) 0.2718(2) 0.09787(8) 0.0356(7) Uani 1 1 d . . . . .
H61 H -0.122(3) 0.313(3) 0.1094(11) 0.044(11) Uiso 1 1 d . . . . .
C43 C -0.3723(3) 0.9121(2) 0.09713(8) 0.0238(6) Uani 1 1 d . . . . .
C44 C 0.2186(3) 0.6535(3) 0.04987(10) 0.0365(8) Uani 1 1 d . . . . .
H63 H 0.1492 0.6543 0.0358 0.044 Uiso 1 1 calc R U . . .
C45 C -0.2121(3) 0.2211(2) 0.19043(9) 0.0313(7) Uani 1 1 d . . . . .
H9 H -0.2355 0.2765 0.1766 0.038 Uiso 1 1 calc R U . . .
C46 C 0.0113(3) 0.8705(2) 0.17597(9) 0.0287(7) Uani 1 1 d . . . . .
H33 H -0.0022 0.8972 0.1513 0.034 Uiso 1 1 calc R U . . .
H34 H -0.0575 0.8868 0.1910 0.034 Uiso 1 1 calc R U . . .
C47 C 0.0390(2) 0.5534(2) 0.16994(7) 0.0191(5) Uani 1 1 d . . . . .
C48 C -0.3473(3) 1.0336(2) 0.04984(8) 0.0251(6) Uani 1 1 d . . . . .
C49 C 0.4208(3) 0.6711(2) 0.05299(9) 0.0317(7) Uani 1 1 d . . . . .
H64 H 0.4925 0.6849 0.0411 0.038 Uiso 1 1 calc R U . . .
C50 C -0.3798(3) 0.7912(3) 0.26077(8) 0.0327(7) Uani 1 1 d . . . . .
H35 H -0.3229 0.8436 0.2664 0.039 Uiso 1 1 calc R U . . .
H36 H -0.4359 0.7868 0.2811 0.039 Uiso 1 1 calc R U . . .
C51 C 0.5889(3) 0.5085(3) 0.18447(10) 0.0406(8) Uani 1 1 d . . . . .
H37 H 0.5849 0.4670 0.1625 0.049 Uiso 1 1 calc R U . . .
H38 H 0.6368 0.5668 0.1787 0.049 Uiso 1 1 calc R U . . .
C52 C -0.3169(3) 0.6942(2) 0.25623(8) 0.0298(7) Uani 1 1 d . . . . .
H39 H -0.3737 0.6428 0.2494 0.036 Uiso 1 1 calc R U . . .
H40 H -0.2808 0.6751 0.2796 0.036 Uiso 1 1 calc R U . . .
C53 C 0.2348(3) 0.7699(2) 0.19415(10) 0.0292(7) Uani 1 1 d . . . . .
H41 H 0.2509 0.7534 0.2198 0.035 Uiso 1 1 calc R U . . .
H42 H 0.3027 0.7486 0.1796 0.035 Uiso 1 1 calc R U . . .
C54 C -0.6983(3) 0.9577(2) 0.01193(9) 0.0300(7) Uani 1 1 d . . . . .
H10 H -0.6444 0.9787 -0.0060 0.036 Uiso 1 1 calc R U . . .
C55 C -0.1460(3) 0.0603(2) 0.23163(9) 0.0347(8) Uani 1 1 d . . . . .
H11 H -0.1235 0.0054 0.2459 0.042 Uiso 1 1 calc R U . . .
C56 C 0.0252(3) 0.3117(3) 0.08107(10) 0.0403(8) Uani 1 1 d . . . . .
H56 H 0.0287 0.3807 0.0778 0.048 Uiso 1 1 calc R U . . .
C57 C -0.7416(3) 0.9078(2) 0.07291(9) 0.0303(7) Uani 1 1 d . . . . .
H12 H -0.7177 0.8963 0.0972 0.036 Uiso 1 1 calc R U . . .
C58 C -0.8567(3) 0.8922(2) 0.06329(11) 0.0364(7) Uani 1 1 d . . . . .
H13 H -0.9106 0.8686 0.0808 0.044 Uiso 1 1 calc R U . . .
C59 C 0.3144(3) 0.6324(2) 0.10630(9) 0.0355(7) Uani 1 1 d . . . . .
H65 H 0.3118 0.6179 0.1315 0.043 Uiso 1 1 calc R U . . .
C60 C -0.8932(3) 0.9110(3) 0.02811(11) 0.0388(8) Uani 1 1 d . . . . .
H14 H -0.9723 0.9008 0.0216 0.047 Uiso 1 1 calc R U . . .
C61 C -0.0634(3) 0.1289(2) 0.22126(9) 0.0298(7) Uani 1 1 d . . . . .
H15 H 0.0154 0.1209 0.2286 0.036 Uiso 1 1 calc R U . . .
C62 C 0.3208(3) 0.1676(2) 0.14223(10) 0.0397(8) Uani 1 1 d . . . . .
H16 H 0.2615 0.1228 0.1491 0.048 Uiso 1 1 calc R U . . .
C63 C -0.3034(4) 1.2050(2) 0.03013(11) 0.0421(9) Uani 1 1 d . . . . .
H17 H -0.3725 1.2262 0.0419 0.051 Uiso 1 1 calc R U . . .
C64 C 0.3884(3) 0.3297(3) 0.13386(12) 0.0462(10) Uani 1 1 d . . . . .
H18 H 0.3769 0.3985 0.1352 0.055 Uiso 1 1 calc R U . . .
C65 C -0.8153(3) 0.9443(2) 0.00270(9) 0.0362(8) Uani 1 1 d . . . . .
H19 H -0.8409 0.9582 -0.0213 0.043 Uiso 1 1 calc R U . . .
C66 C -0.2942(3) 0.1519(3) 0.20096(10) 0.0384(8) Uani 1 1 d . . . . .
H20 H -0.3735 0.1599 0.1942 0.046 Uiso 1 1 calc R U . . .
C67 C -0.2611(3) 0.0715(3) 0.22128(10) 0.0393(8) Uani 1 1 d . . . . .
H21 H -0.3174 0.0239 0.2281 0.047 Uiso 1 1 calc R U . . .
C68 C -0.1712(3) 1.0775(3) 0.01364(12) 0.0462(9) Uani 1 1 d . . . . .
H22 H -0.1482 1.0106 0.0144 0.055 Uiso 1 1 calc R U . . .
C69 C 0.1148(3) 0.2536(3) 0.06838(11) 0.0464(9) Uani 1 1 d . . . . .
H57 H 0.1800 0.2817 0.0564 0.056 Uiso 1 1 calc R U . . .
C70 C 0.1075(4) 0.1530(3) 0.07353(12) 0.0513(11) Uani 1 1 d . . . . .
H58 H 0.1682 0.1114 0.0652 0.062 Uiso 1 1 calc R U . . .
C71 C 0.0118(4) 0.1138(3) 0.09084(12) 0.0499(10) Uani 1 1 d . . . . .
H59 H 0.0057 0.0450 0.0943 0.060 Uiso 1 1 calc R U . . .
C72 C 0.5142(3) 0.1950(3) 0.11965(11) 0.0470(10) Uani 1 1 d . . . . .
H23 H 0.5867 0.1702 0.1113 0.056 Uiso 1 1 calc R U . . .
C73 C -0.0749(4) 0.1754(3) 0.10301(11) 0.0430(9) Uani 1 1 d . . . . .
H60 H -0.1409 0.1490 0.1151 0.052 Uiso 1 1 calc R U . . .
C74 C 0.2127(3) 0.6344(3) 0.08647(10) 0.0405(9) Uani 1 1 d . . . . .
H66 H 0.1397 0.6227 0.0979 0.049 Uiso 1 1 calc R U . . .
C75 C 0.1173(4) 0.9195(3) 0.1921(2) 0.097(3) Uani 1 1 d . . . . .
H43 H 0.1247 0.9843 0.1802 0.117 Uiso 1 1 calc R U . . .
H44 H 0.0997 0.9321 0.2180 0.117 Uiso 1 1 calc R U . . .
C76 C -0.2323(4) 1.2731(3) 0.01226(13) 0.0561(12) Uani 1 1 d . . . . .
H24 H -0.2528 1.3406 0.0122 0.067 Uiso 1 1 calc R U . . .
C77 C 0.4948(3) 0.2941(3) 0.12131(13) 0.0538(11) Uani 1 1 d . . . . .
H25 H 0.5540 0.3385 0.1139 0.065 Uiso 1 1 calc R U . . .
C78 C -0.1339(4) 1.2429(3) -0.00499(14) 0.0619(13) Uani 1 1 d . . . . .
H26 H -0.0867 1.2892 -0.0174 0.074 Uiso 1 1 calc R U . . .
C79 C 0.2222(4) 0.8773(3) 0.1908(2) 0.088(2) Uani 1 1 d . . . . .
H45 H 0.2698 0.9072 0.2103 0.105 Uiso 1 1 calc R U . . .
H46 H 0.2584 0.8965 0.1675 0.105 Uiso 1 1 calc R U . . .
C80 C 0.4271(4) 0.1319(3) 0.13028(11) 0.0503(11) Uani 1 1 d . . . . .
H27 H 0.4400 0.0632 0.1294 0.060 Uiso 1 1 calc R U . . .
C81 C -0.1023(4) 1.1456(3) -0.00460(15) 0.0609(13) Uani 1 1 d . . . . .
H28 H -0.0336 1.1249 -0.0168 0.073 Uiso 1 1 calc R U . . .
H67 H 0.330(4) 0.688(3) 0.0071(13) 0.070(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
P1 O7 1.501(2) . ?
P1 O8 1.505(2) . ?
P1 O13 1.555(2) . ?
P1 O6 1.630(2) . ?
P2 O9 1.495(2) . ?
P2 O10 1.499(2) . ?
P2 O11 1.560(2) . ?
P2 O5 1.622(2) . ?
Cl1 C51 1.774(4) . ?
Cl0 C51 1.759(4) . ?
O5 C12 1.400(3) . ?
O6 C34 1.395(3) . ?
O11 H48 0.80(5) . ?
C12 C16 1.390(4) . ?
C12 C19 1.403(4) . ?
O13 H47 0.81(4) . ?
C14 C17 1.397(4) . ?
C14 C18 1.403(4) . ?
C14 C47 1.490(4) . ?
C15 C31 1.398(4) . ?
C15 C23 1.411(4) . ?
C15 C46 1.515(4) . ?
C16 C25 1.411(4) . ?
C16 C23 1.501(4) . ?
C17 C32 1.402(4) . ?
C17 H1 0.9500 . ?
C18 C22 1.396(4) . ?
C18 H2 0.9500 . ?
C19 C33 1.394(4) . ?
C19 C43 1.493(4) . ?
C20 C31 1.389(4) . ?
C20 C47 1.392(4) . ?
C20 H3 0.9500 . ?
C21 C25 1.519(4) . ?
C21 C52 1.533(4) . ?
C21 H29 0.9900 . ?
C21 H30 0.9900 . ?
C22 C38 1.401(4) . ?
C22 C39 1.500(4) . ?
C23 C34 1.392(4) . ?
C24 C33 1.389(4) . ?
C24 C25 1.401(4) . ?
C24 C41 1.516(4) . ?
N0 C49 1.340(4) . ?
N0 C44 1.342(5) . ?
N0 H67 1.02(5) . ?
C27 C57 1.399(5) . ?
C27 C54 1.399(4) . ?
C27 C28 1.491(4) . ?
C28 C36 1.398(4) . ?
C28 C30 1.399(4) . ?
C29 C43 1.388(4) . ?
C29 C48 1.398(4) . ?
C29 H4 0.9500 . ?
C30 C48 1.395(4) . ?
C30 H5 0.9500 . ?
C31 C53 1.520(4) . ?
C32 C38 1.389(4) . ?
C32 C35 1.496(4) . ?
C33 H6 0.9500 . ?
C34 C47 1.405(4) . ?
C35 C61 1.397(4) . ?
C35 C45 1.402(5) . ?
C36 C43 1.389(4) . ?
C36 H7 0.9500 . ?
C37 C68 1.384(5) . ?
C37 C63 1.386(4) . ?
C37 C48 1.491(4) . ?
C38 H8 0.9500 . ?
C39 C64 1.383(5) . ?
C39 C62 1.394(4) . ?
C40 C49 1.381(5) . ?
C40 C59 1.386(5) . ?
C40 H62 0.9500 . ?
C41 C50 1.524(4) . ?
C41 H31 0.9900 . ?
C41 H32 0.9900 . ?
N1 C73 1.333(5) . ?
N1 C56 1.336(5) . ?
N1 H61 0.95(4) . ?
C44 C74 1.376(5) . ?
C44 H63 0.9500 . ?
C45 C66 1.390(5) . ?
C45 H9 0.9500 . ?
C46 C75 1.509(5) . ?
C46 H33 0.9900 . ?
C46 H34 0.9900 . ?
C49 H64 0.9500 . ?
C50 C52 1.516(4) . ?
C50 H35 0.9900 . ?
C50 H36 0.9900 . ?
C51 H37 0.9900 . ?
C51 H38 0.9900 . ?
C52 H39 0.9900 . ?
C52 H40 0.9900 . ?
C53 C79 1.477(5) . ?
C53 H41 0.9900 . ?
C53 H42 0.9900 . ?
C54 C65 1.397(5) . ?
C54 H10 0.9500 . ?
C55 C67 1.384(5) . ?
C55 C61 1.386(5) . ?
C55 H11 0.9500 . ?
C56 C69 1.380(5) . ?
C56 H56 0.9500 . ?
C57 C58 1.384(5) . ?
C57 H12 0.9500 . ?
C58 C60 1.386(5) . ?
C58 H13 0.9500 . ?
C59 C74 1.377(5) . ?
C59 H65 0.9500 . ?
C60 C65 1.372(5) . ?
C60 H14 0.9500 . ?
C61 H15 0.9500 . ?
C62 C80 1.386(5) . ?
C62 H16 0.9500 . ?
C63 C76 1.401(5) . ?
C63 H17 0.9500 . ?
C64 C77 1.393(5) . ?
C64 H18 0.9500 . ?
C65 H19 0.9500 . ?
C66 C67 1.382(5) . ?
C66 H20 0.9500 . ?
C67 H21 0.9500 . ?
C68 C81 1.392(5) . ?
C68 H22 0.9500 . ?
C69 C70 1.387(6) . ?
C69 H57 0.9500 . ?
C70 C71 1.378(6) . ?
C70 H58 0.9500 . ?
C71 C73 1.377(5) . ?
C71 H59 0.9500 . ?
C72 C77 1.372(6) . ?
C72 C80 1.376(6) . ?
C72 H23 0.9500 . ?
C73 H60 0.9500 . ?
C74 H66 0.9500 . ?
C75 C79 1.336(6) . ?
C75 H43 0.9900 . ?
C75 H44 0.9900 . ?
C76 C78 1.359(7) . ?
C76 H24 0.9500 . ?
C77 H25 0.9500 . ?
C78 C81 1.376(7) . ?
C78 H26 0.9500 . ?
C79 H45 0.9900 . ?
C79 H46 0.9900 . ?
C80 H27 0.9500 . ?
C81 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O7 P1 O8 116.53(12) . . ?
O7 P1 O13 107.45(13) . . ?
O8 P1 O13 113.52(12) . . ?
O7 P1 O6 106.64(11) . . ?
O8 P1 O6 108.32(11) . . ?
O13 P1 O6 103.38(12) . . ?
O9 P2 O10 117.58(13) . . ?
O9 P2 O11 113.18(12) . . ?
O10 P2 O11 107.46(13) . . ?
O9 P2 O5 108.03(11) . . ?
O10 P2 O5 105.81(11) . . ?
O11 P2 O5 103.63(12) . . ?
C12 O5 P2 122.98(18) . . ?
C34 O6 P1 124.79(17) . . ?
P2 O11 H48 111(3) . . ?
C16 C12 O5 118.5(2) . . ?
C16 C12 C19 121.4(2) . . ?
O5 C12 C19 120.0(2) . . ?
P1 O13 H47 110(3) . . ?
C17 C14 C18 118.9(2) . . ?
C17 C14 C47 122.8(3) . . ?
C18 C14 C47 118.2(2) . . ?
C31 C15 C23 119.5(2) . . ?
C31 C15 C46 120.7(3) . . ?
C23 C15 C46 119.7(2) . . ?
C12 C16 C25 120.0(2) . . ?
C12 C16 C23 121.8(2) . . ?
C25 C16 C23 117.9(2) . . ?
C14 C17 C32 120.5(3) . . ?
C14 C17 H1 119.8 . . ?
C32 C17 H1 119.8 . . ?
C22 C18 C14 122.0(3) . . ?
C22 C18 H2 119.0 . . ?
C14 C18 H2 119.0 . . ?
C33 C19 C12 117.1(3) . . ?
C33 C19 C43 119.1(3) . . ?
C12 C19 C43 123.9(3) . . ?
C31 C20 C47 123.5(3) . . ?
C31 C20 H3 118.2 . . ?
C47 C20 H3 118.2 . . ?
C25 C21 C52 113.6(2) . . ?
C25 C21 H29 108.8 . . ?
C52 C21 H29 108.8 . . ?
C25 C21 H30 108.8 . . ?
C52 C21 H30 108.8 . . ?
H29 C21 H30 107.7 . . ?
C18 C22 C38 117.3(3) . . ?
C18 C22 C39 120.8(3) . . ?
C38 C22 C39 121.9(2) . . ?
C34 C23 C15 120.1(2) . . ?
C34 C23 C16 120.8(2) . . ?
C15 C23 C16 118.6(2) . . ?
C33 C24 C25 118.5(3) . . ?
C33 C24 C41 119.2(3) . . ?
C25 C24 C41 122.2(3) . . ?
C24 C25 C16 119.6(3) . . ?
C24 C25 C21 120.5(2) . . ?
C16 C25 C21 119.8(2) . . ?
C49 N0 C44 121.2(3) . . ?
C49 N0 H67 116(3) . . ?
C44 N0 H67 123(3) . . ?
C57 C27 C54 118.0(3) . . ?
C57 C27 C28 120.7(3) . . ?
C54 C27 C28 121.2(3) . . ?
C36 C28 C30 117.8(3) . . ?
C36 C28 C27 120.3(3) . . ?
C30 C28 C27 121.8(3) . . ?
C43 C29 C48 120.8(3) . . ?
C43 C29 H4 119.6 . . ?
C48 C29 H4 119.6 . . ?
C48 C30 C28 121.2(3) . . ?
C48 C30 H5 119.4 . . ?
C28 C30 H5 119.4 . . ?
C20 C31 C15 118.6(3) . . ?
C20 C31 C53 118.9(3) . . ?
C15 C31 C53 122.4(2) . . ?
C38 C32 C17 118.9(3) . . ?
C38 C32 C35 119.7(3) . . ?
C17 C32 C35 121.2(3) . . ?
C24 C33 C19 123.4(3) . . ?
C24 C33 H6 118.3 . . ?
C19 C33 H6 118.3 . . ?
C23 C34 O6 118.2(2) . . ?
C23 C34 C47 121.2(3) . . ?
O6 C34 C47 120.4(2) . . ?
C61 C35 C45 118.6(3) . . ?
C61 C35 C32 120.9(3) . . ?
C45 C35 C32 120.5(3) . . ?
C43 C36 C28 122.1(3) . . ?
C43 C36 H7 118.9 . . ?
C28 C36 H7 118.9 . . ?
C68 C37 C63 119.0(3) . . ?
C68 C37 C48 120.4(3) . . ?
C63 C37 C48 120.6(3) . . ?
C32 C38 C22 122.4(3) . . ?
C32 C38 H8 118.8 . . ?
C22 C38 H8 118.8 . . ?
C64 C39 C62 116.7(3) . . ?
C64 C39 C22 121.8(3) . . ?
C62 C39 C22 121.5(3) . . ?
C49 C40 C59 118.1(3) . . ?
C49 C40 H62 120.9 . . ?
C59 C40 H62 120.9 . . ?
C24 C41 C50 112.8(3) . . ?
C24 C41 H31 109.0 . . ?
C50 C41 H31 109.0 . . ?
C24 C41 H32 109.0 . . ?
C50 C41 H32 109.0 . . ?
H31 C41 H32 107.8 . . ?
C73 N1 C56 121.7(3) . . ?
C73 N1 H61 118(2) . . ?
C56 N1 H61 120(2) . . ?
C29 C43 C36 118.8(3) . . ?
C29 C43 C19 122.9(3) . . ?
C36 C43 C19 118.2(3) . . ?
N0 C44 C74 120.6(3) . . ?
N0 C44 H63 119.7 . . ?
C74 C44 H63 119.7 . . ?
C66 C45 C35 120.3(3) . . ?
C66 C45 H9 119.9 . . ?
C35 C45 H9 119.9 . . ?
C75 C46 C15 113.4(3) . . ?
C75 C46 H33 108.9 . . ?
C15 C46 H33 108.9 . . ?
C75 C46 H34 108.9 . . ?
C15 C46 H34 108.9 . . ?
H33 C46 H34 107.7 . . ?
C20 C47 C34 117.0(2) . . ?
C20 C47 C14 118.4(2) . . ?
C34 C47 C14 124.6(3) . . ?
C30 C48 C29 119.2(3) . . ?
C30 C48 C37 120.2(3) . . ?
C29 C48 C37 120.6(3) . . ?
N0 C49 C40 120.8(3) . . ?
N0 C49 H64 119.6 . . ?
C40 C49 H64 119.6 . . ?
C52 C50 C41 109.1(3) . . ?
C52 C50 H35 109.9 . . ?
C41 C50 H35 109.9 . . ?
C52 C50 H36 109.9 . . ?
C41 C50 H36 109.9 . . ?
H35 C50 H36 108.3 . . ?
Cl0 C51 Cl1 110.9(2) . . ?
Cl0 C51 H37 109.5 . . ?
Cl1 C51 H37 109.5 . . ?
Cl0 C51 H38 109.5 . . ?
Cl1 C51 H38 109.5 . . ?
H37 C51 H38 108.0 . . ?
C50 C52 C21 110.8(3) . . ?
C50 C52 H39 109.5 . . ?
C21 C52 H39 109.5 . . ?
C50 C52 H40 109.5 . . ?
C21 C52 H40 109.5 . . ?
H39 C52 H40 108.1 . . ?
C79 C53 C31 113.4(3) . . ?
C79 C53 H41 108.9 . . ?
C31 C53 H41 108.9 . . ?
C79 C53 H42 108.9 . . ?
C31 C53 H42 108.9 . . ?
H41 C53 H42 107.7 . . ?
C65 C54 C27 120.5(3) . . ?
C65 C54 H10 119.8 . . ?
C27 C54 H10 119.8 . . ?
C67 C55 C61 120.2(3) . . ?
C67 C55 H11 119.9 . . ?
C61 C55 H11 119.9 . . ?
N1 C56 C69 120.6(4) . . ?
N1 C56 H56 119.7 . . ?
C69 C56 H56 119.7 . . ?
C58 C57 C27 121.1(3) . . ?
C58 C57 H12 119.5 . . ?
C27 C57 H12 119.5 . . ?
C57 C58 C60 120.0(3) . . ?
C57 C58 H13 120.0 . . ?
C60 C58 H13 120.0 . . ?
C74 C59 C40 120.5(3) . . ?
C74 C59 H65 119.8 . . ?
C40 C59 H65 119.8 . . ?
C65 C60 C58 120.1(3) . . ?
C65 C60 H14 119.9 . . ?
C58 C60 H14 119.9 . . ?
C55 C61 C35 120.7(3) . . ?
C55 C61 H15 119.7 . . ?
C35 C61 H15 119.7 . . ?
C80 C62 C39 121.4(4) . . ?
C80 C62 H16 119.3 . . ?
C39 C62 H16 119.3 . . ?
C37 C63 C76 120.1(4) . . ?
C37 C63 H17 119.9 . . ?
C76 C63 H17 119.9 . . ?
C39 C64 C77 122.1(3) . . ?
C39 C64 H18 118.9 . . ?
C77 C64 H18 118.9 . . ?
C60 C65 C54 120.2(3) . . ?
C60 C65 H19 119.9 . . ?
C54 C65 H19 119.9 . . ?
C67 C66 C45 120.3(3) . . ?
C67 C66 H20 119.8 . . ?
C45 C66 H20 119.8 . . ?
C66 C67 C55 119.9(3) . . ?
C66 C67 H21 120.0 . . ?
C55 C67 H21 120.0 . . ?
C37 C68 C81 120.3(4) . . ?
C37 C68 H22 119.8 . . ?
C81 C68 H22 119.8 . . ?
C56 C69 C70 118.4(4) . . ?
C56 C69 H57 120.8 . . ?
C70 C69 H57 120.8 . . ?
C71 C70 C69 119.7(4) . . ?
C71 C70 H58 120.1 . . ?
C69 C70 H58 120.1 . . ?
C73 C71 C70 119.3(4) . . ?
C73 C71 H59 120.3 . . ?
C70 C71 H59 120.3 . . ?
C77 C72 C80 119.1(3) . . ?
C77 C72 H23 120.5 . . ?
C80 C72 H23 120.5 . . ?
N1 C73 C71 120.2(4) . . ?
N1 C73 H60 119.9 . . ?
C71 C73 H60 119.9 . . ?
C44 C74 C59 118.8(3) . . ?
C44 C74 H66 120.6 . . ?
C59 C74 H66 120.6 . . ?
C79 C75 C46 121.4(4) . . ?
C79 C75 H43 107.0 . . ?
C46 C75 H43 107.0 . . ?
C79 C75 H44 107.0 . . ?
C46 C75 H44 107.0 . . ?
H43 C75 H44 106.7 . . ?
C78 C76 C63 120.1(4) . . ?
C78 C76 H24 119.9 . . ?
C63 C76 H24 119.9 . . ?
C72 C77 C64 120.0(4) . . ?
C72 C77 H25 120.0 . . ?
C64 C77 H25 120.0 . . ?
C76 C78 C81 120.5(4) . . ?
C76 C78 H26 119.8 . . ?
C81 C78 H26 119.8 . . ?
C75 C79 C53 120.9(4) . . ?
C75 C79 H45 107.1 . . ?
C53 C79 H45 107.1 . . ?
C75 C79 H46 107.1 . . ?
C53 C79 H46 107.1 . . ?
H45 C79 H46 106.8 . . ?
C72 C80 C62 120.7(3) . . ?
C72 C80 H27 119.7 . . ?
C62 C80 H27 119.7 . . ?
C78 C81 C68 119.9(4) . . ?
C78 C81 H28 120.0 . . ?
C68 C81 H28 120.0 . . ?

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
O9 P2 O5 C12 -0.8(2) . . . . ?
O10 P2 O5 C12 125.9(2) . . . . ?
O11 P2 O5 C12 -121.2(2) . . . . ?
O7 P1 O6 C34 126.5(2) . . . . ?
O8 P1 O6 C34 0.3(2) . . . . ?
O13 P1 O6 C34 -120.4(2) . . . . ?
P2 O5 C12 C16 110.6(2) . . . . ?
P2 O5 C12 C19 -72.8(3) . . . . ?
O5 C12 C16 C25 175.2(2) . . . . ?
C19 C12 C16 C25 -1.4(4) . . . . ?
O5 C12 C16 C23 1.6(4) . . . . ?
C19 C12 C16 C23 -175.0(3) . . . . ?
C18 C14 C17 C32 1.3(4) . . . . ?
C47 C14 C17 C32 -175.2(3) . . . . ?
C17 C14 C18 C22 -2.1(4) . . . . ?
C47 C14 C18 C22 174.6(3) . . . . ?
C16 C12 C19 C33 1.2(4) . . . . ?
O5 C12 C19 C33 -175.3(3) . . . . ?
C16 C12 C19 C43 -179.4(3) . . . . ?
O5 C12 C19 C43 4.1(4) . . . . ?
C14 C18 C22 C38 1.1(4) . . . . ?
C14 C18 C22 C39 -179.2(3) . . . . ?
C31 C15 C23 C34 -2.0(4) . . . . ?
C46 C15 C23 C34 -179.9(3) . . . . ?
C31 C15 C23 C16 169.9(3) . . . . ?
C46 C15 C23 C16 -8.1(4) . . . . ?
C12 C16 C23 C34 -106.4(3) . . . . ?
C25 C16 C23 C34 79.9(3) . . . . ?
C12 C16 C23 C15 81.8(3) . . . . ?
C25 C16 C23 C15 -91.9(3) . . . . ?
C33 C24 C25 C16 1.0(4) . . . . ?
C41 C24 C25 C16 -176.5(3) . . . . ?
C33 C24 C25 C21 177.9(3) . . . . ?
C41 C24 C25 C21 0.4(4) . . . . ?
C12 C16 C25 C24 0.3(4) . . . . ?
C23 C16 C25 C24 174.1(2) . . . . ?
C12 C16 C25 C21 -176.6(3) . . . . ?
C23 C16 C25 C21 -2.8(4) . . . . ?
C52 C21 C25 C24 13.1(4) . . . . ?
C52 C21 C25 C16 -170.0(3) . . . . ?
C57 C27 C28 C36 25.9(4) . . . . ?
C54 C27 C28 C36 -152.9(3) . . . . ?
C57 C27 C28 C30 -153.4(3) . . . . ?
C54 C27 C28 C30 27.8(4) . . . . ?
C36 C28 C30 C48 0.2(4) . . . . ?
C27 C28 C30 C48 179.5(3) . . . . ?
C47 C20 C31 C15 1.5(4) . . . . ?
C47 C20 C31 C53 178.4(3) . . . . ?
C23 C15 C31 C20 0.2(4) . . . . ?
C46 C15 C31 C20 178.1(3) . . . . ?
C23 C15 C31 C53 -176.6(3) . . . . ?
C46 C15 C31 C53 1.3(4) . . . . ?
C14 C17 C32 C38 0.3(4) . . . . ?
C14 C17 C32 C35 -176.1(3) . . . . ?
C25 C24 C33 C19 -1.3(5) . . . . ?
C41 C24 C33 C19 176.4(3) . . . . ?
C12 C19 C33 C24 0.2(4) . . . . ?
C43 C19 C33 C24 -179.2(3) . . . . ?
C15 C23 C34 O6 177.1(2) . . . . ?
C16 C23 C34 O6 5.4(4) . . . . ?
C15 C23 C34 C47 2.2(4) . . . . ?
C16 C23 C34 C47 -169.5(3) . . . . ?
P1 O6 C34 C23 105.5(3) . . . . ?
P1 O6 C34 C47 -79.6(3) . . . . ?
C38 C32 C35 C61 40.9(4) . . . . ?
C17 C32 C35 C61 -142.8(3) . . . . ?
C38 C32 C35 C45 -136.4(3) . . . . ?
C17 C32 C35 C45 39.9(4) . . . . ?
C30 C28 C36 C43 -0.2(4) . . . . ?
C27 C28 C36 C43 -179.5(3) . . . . ?
C17 C32 C38 C22 -1.3(4) . . . . ?
C35 C32 C38 C22 175.1(3) . . . . ?
C18 C22 C38 C32 0.6(4) . . . . ?
C39 C22 C38 C32 -179.1(3) . . . . ?
C18 C22 C39 C64 9.5(5) . . . . ?
C38 C22 C39 C64 -170.8(3) . . . . ?
C18 C22 C39 C62 -172.6(3) . . . . ?
C38 C22 C39 C62 7.1(4) . . . . ?
C33 C24 C41 C50 -159.1(3) . . . . ?
C25 C24 C41 C50 18.5(4) . . . . ?
C48 C29 C43 C36 0.9(4) . . . . ?
C48 C29 C43 C19 -175.8(3) . . . . ?
C28 C36 C43 C29 -0.4(4) . . . . ?
C28 C36 C43 C19 176.5(3) . . . . ?
C33 C19 C43 C29 130.1(3) . . . . ?
C12 C19 C43 C29 -49.2(4) . . . . ?
C33 C19 C43 C36 -46.6(4) . . . . ?
C12 C19 C43 C36 134.1(3) . . . . ?
C49 N0 C44 C74 -0.6(5) . . . . ?
C61 C35 C45 C66 -1.7(5) . . . . ?
C32 C35 C45 C66 175.7(3) . . . . ?
C31 C15 C46 C75 -7.0(5) . . . . ?
C23 C15 C46 C75 170.8(4) . . . . ?
C31 C20 C47 C34 -1.3(4) . . . . ?
C31 C20 C47 C14 -178.7(3) . . . . ?
C23 C34 C47 C20 -0.5(4) . . . . ?
O6 C34 C47 C20 -175.3(2) . . . . ?
C23 C34 C47 C14 176.6(3) . . . . ?
O6 C34 C47 C14 1.8(4) . . . . ?
C17 C14 C47 C20 134.8(3) . . . . ?
C18 C14 C47 C20 -41.7(4) . . . . ?
C17 C14 C47 C34 -42.3(4) . . . . ?
C18 C14 C47 C34 141.2(3) . . . . ?
C28 C30 C48 C29 0.3(4) . . . . ?
C28 C30 C48 C37 -178.7(3) . . . . ?
C43 C29 C48 C30 -0.9(4) . . . . ?
C43 C29 C48 C37 178.1(3) . . . . ?
C68 C37 C48 C30 -121.9(4) . . . . ?
C63 C37 C48 C30 59.3(4) . . . . ?
C68 C37 C48 C29 59.1(4) . . . . ?
C63 C37 C48 C29 -119.8(4) . . . . ?
C44 N0 C49 C40 1.3(5) . . . . ?
C59 C40 C49 N0 -0.6(5) . . . . ?
C24 C41 C50 C52 -49.8(4) . . . . ?
C41 C50 C52 C21 64.1(4) . . . . ?
C25 C21 C52 C50 -45.3(4) . . . . ?
C20 C31 C53 C79 173.7(4) . . . . ?
C15 C31 C53 C79 -9.5(5) . . . . ?
C57 C27 C54 C65 1.1(4) . . . . ?
C28 C27 C54 C65 179.9(3) . . . . ?
C73 N1 C56 C69 0.0(5) . . . . ?
C54 C27 C57 C58 0.6(4) . . . . ?
C28 C27 C57 C58 -178.2(3) . . . . ?
C27 C57 C58 C60 -1.5(5) . . . . ?
C49 C40 C59 C74 -0.8(5) . . . . ?
C57 C58 C60 C65 0.6(5) . . . . ?
C67 C55 C61 C35 -0.4(5) . . . . ?
C45 C35 C61 C55 1.7(5) . . . . ?
C32 C35 C61 C55 -175.7(3) . . . . ?
C64 C39 C62 C80 0.2(5) . . . . ?
C22 C39 C62 C80 -177.8(3) . . . . ?
C68 C37 C63 C76 0.6(6) . . . . ?
C48 C37 C63 C76 179.5(3) . . . . ?
C62 C39 C64 C77 0.8(6) . . . . ?
C22 C39 C64 C77 178.8(4) . . . . ?
C58 C60 C65 C54 1.2(5) . . . . ?
C27 C54 C65 C60 -2.0(5) . . . . ?
C35 C45 C66 C67 0.4(5) . . . . ?
C45 C66 C67 C55 0.8(5) . . . . ?
C61 C55 C67 C66 -0.8(5) . . . . ?
C63 C37 C68 C81 -1.8(6) . . . . ?
C48 C37 C68 C81 179.3(4) . . . . ?
N1 C56 C69 C70 -0.1(5) . . . . ?
C56 C69 C70 C71 0.3(6) . . . . ?
C69 C70 C71 C73 -0.5(6) . . . . ?
C56 N1 C73 C71 -0.1(5) . . . . ?
C70 C71 C73 N1 0.4(6) . . . . ?
N0 C44 C74 C59 -0.7(6) . . . . ?
C40 C59 C74 C44 1.4(5) . . . . ?
C15 C46 C75 C79 24.3(9) . . . . ?
C37 C63 C76 C78 0.8(6) . . . . ?
C80 C72 C77 C64 0.4(7) . . . . ?
C39 C64 C77 C72 -1.1(7) . . . . ?
C63 C76 C78 C81 -1.0(7) . . . . ?
C46 C75 C79 C53 -35.6(11) . . . . ?
C31 C53 C79 C75 26.7(8) . . . . ?
C77 C72 C80 C62 0.5(6) . . . . ?
C39 C62 C80 C72 -0.9(6) . . . . ?
C76 C78 C81 C68 -0.1(7) . . . . ?
C37 C68 C81 C78 1.6(7) . . . . ?

_refine_diff_density_max         0.493
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.046

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_CrystalClear_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1834632'
_audit_update_record             
;
2018-04-04 deposited with the CCDC.
2018-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            
"2'-((Hydroxy(isopropoxy)phosphoryl)oxy)-3-(2,4,6-tricyclohexylphenyl)-[1,1'-binaphthalen]-2-yl dihydrogen phosphate (R/S-Dimer)"
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C47 H56 O8 P2'
_chemical_formula_weight         810.85

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'
P P 0.1023 0.0942 '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                   12.7831(18)
_cell_length_b                   14.6459(16)
_cell_length_c                   14.800(2)
_cell_angle_alpha                116.231(11)
_cell_angle_beta                 101.896(13)
_cell_angle_gamma                102.26(2)
_cell_volume                     2282.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    7720
_cell_measurement_theta_min      3.005
_cell_measurement_theta_max      27.485

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   0.854
_exptl_transmission_factor_max   1.000
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Rigaku CrystalClear'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PILATUS 200K area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19527
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.005
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             9800
_reflns_number_gt                8336
_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       'Rigaku CrystalClear'
_computing_cell_refinement       'Rigaku CrystalClear'
_computing_data_reduction        'Rigaku CrystalClear'
_computing_structure_solution    'Rigaku CrystalStructure'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Rigaku CrystalStructure'
_computing_publication_material  'Rigaku CrystalStructure'
_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)+(0.0986P)²+0.5986P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9800
_refine_ls_number_parameters     532
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1510
_refine_ls_wR_factor_gt          0.1472
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 243 26 ' '
2 0.000 0.500 1.000 22 2 ' '
_platon_squeeze_details          ?


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
P1 P 0.65695(3) 0.51946(3) 0.08892(3) 0.01841(11) Uani 1 1 d . . . . .
P2 P 0.40429(4) 0.62566(4) 0.26344(3) 0.02692(12) Uani 1 1 d . . . . .
O1 O 0.73030(9) 0.52116(8) 0.18928(8) 0.0193(2) Uani 1 1 d . . . . .
O2 O 0.59826(9) 0.60063(8) 0.11976(8) 0.0220(2) Uani 1 1 d . . . . .
O3 O 0.57234(10) 0.40058(9) 0.01877(9) 0.0242(2) Uani 1 1 d . . . . .
O5 O 0.44202(10) 0.54974(10) 0.30273(9) 0.0273(3) Uani 1 1 d . . . . .
O8 O 0.37506(11) 0.70185(11) 0.35945(9) 0.0332(3) Uani 1 1 d . . . . .
O4 O 0.74215(11) 0.53922(11) 0.03508(10) 0.0323(3) Uani 1 1 d . . . . .
C1 C 0.66893(13) 0.55728(12) 0.33960(11) 0.0190(3) Uani 1 1 d . . . . .
C3 C 0.83285(13) 0.69256(12) 0.35259(12) 0.0193(3) Uani 1 1 d . . . . .
C4 C 0.84624(14) 0.75982(13) 0.45794(12) 0.0236(3) Uani 1 1 d . . . . .
H4 H 0.9055 0.8286 0.4978 0.028 Uiso 1 1 calc R U . . .
O7 O 0.51307(12) 0.69694(11) 0.26382(11) 0.0342(3) Uani 1 1 d . . . . .
H7A H 0.539(2) 0.662(2) 0.212(2) 0.065(8) Uiso 1 1 d . . . . .
C2 C 0.74171(13) 0.59164(12) 0.29551(11) 0.0179(3) Uani 1 1 d . . . . .
O6 O 0.30592(11) 0.56672(12) 0.16383(10) 0.0373(3) Uani 1 1 d . . . . .
C25 C 0.90228(14) 0.80612(13) 0.27524(12) 0.0231(3) Uani 1 1 d . . . . .
C11 C 0.57034(14) 0.45327(12) 0.27012(11) 0.0218(3) Uani 1 1 d . . . . .
C9 C 0.68724(13) 0.62712(12) 0.45056(11) 0.0205(3) Uani 1 1 d . . . . .
C12 C 0.46167(14) 0.45383(13) 0.24380(12) 0.0246(3) Uani 1 1 d . . . . .
C24 C 0.91095(13) 0.72549(12) 0.30094(12) 0.0212(3) Uani 1 1 d . . . . .
C8 C 0.61974(15) 0.59684(13) 0.50444(12) 0.0254(3) Uani 1 1 d . . . . .
H8 H 0.5623 0.5271 0.4673 0.031 Uiso 1 1 calc R U . . .
C19 C 0.58596(15) 0.35050(13) 0.22776(12) 0.0246(3) Uani 1 1 d . . . . .
C10 C 0.77486(14) 0.73008(13) 0.50874(12) 0.0234(3) Uani 1 1 d . . . . .
C29 C 0.99506(14) 0.67869(13) 0.28243(13) 0.0248(3) Uani 1 1 d . . . . .
C18 C 0.69330(16) 0.34075(14) 0.25964(14) 0.0290(4) Uani 1 1 d . . . . .
H18 H 0.7584 0.4043 0.3064 0.035 Uiso 1 1 calc R U . . .
C26 C 0.98128(15) 0.84019(14) 0.23373(14) 0.0277(3) Uani 1 1 d . . . . .
H26 H 0.9767 0.8952 0.2171 0.033 Uiso 1 1 calc R U . . .
C28 C 1.07160(15) 0.71595(14) 0.24137(14) 0.0293(4) Uani 1 1 d . . . . .
H28 H 1.1297 0.6857 0.2302 0.035 Uiso 1 1 calc R U . . .
C14 C 0.38223(17) 0.26201(15) 0.12297(13) 0.0337(4) Uani 1 1 d . . . . .
H14 H 0.3194 0.1986 0.0698 0.040 Uiso 1 1 calc R U . . .
C30 C 0.81063(14) 0.85603(12) 0.29041(13) 0.0234(3) Uani 1 1 d . . . . .
H30 H 0.7530 0.8101 0.3037 0.028 Uiso 1 1 calc R U . . .
C31 C 0.74811(15) 0.85670(14) 0.19018(14) 0.0290(4) Uani 1 1 d . . . . .
H31 H 0.8031 0.9006 0.1739 0.035 Uiso 1 1 calc R U . . .
H31A H 0.7152 0.7817 0.1281 0.035 Uiso 1 1 calc R U . . .
C21 C 0.46210(16) 0.76999(16) 0.46799(13) 0.0325(4) Uani 1 1 d . . . . .
H21 H 0.532(2) 0.7533(19) 0.4639(19) 0.043(6) Uiso 1 1 d . . . . .
C36 C 1.00654(14) 0.59143(14) 0.30890(14) 0.0271(3) Uani 1 1 d . . . . .
H36 H 0.9361 0.5649 0.3227 0.032 Uiso 1 1 calc R U . . .
C13 C 0.36701(16) 0.35994(15) 0.16763(13) 0.0316(4) Uani 1 1 d . . . . .
H13 H 0.2937 0.3647 0.1477 0.038 Uiso 1 1 calc R U . . .
C6 C 0.72057(17) 0.77110(15) 0.66601(13) 0.0339(4) Uani 1 1 d . . . . .
H6 H 0.7302 0.8199 0.7383 0.041 Uiso 1 1 calc R U . . .
C27 C 1.06573(16) 0.79630(14) 0.21614(14) 0.0298(4) Uani 1 1 d . . . . .
C7 C 0.63637(16) 0.66704(15) 0.60962(13) 0.0300(4) Uani 1 1 d . . . . .
H7 H 0.5908 0.6454 0.6447 0.036 Uiso 1 1 calc R U . . .
C35 C 0.85652(15) 0.97134(14) 0.38817(14) 0.0300(4) Uani 1 1 d . . . . .
H35 H 0.8939 0.9699 0.4529 0.036 Uiso 1 1 calc R U . . .
H35A H 0.9146 1.0188 0.3778 0.036 Uiso 1 1 calc R U . . .
C5 C 0.78811(16) 0.80174(14) 0.61718(13) 0.0318(4) Uani 1 1 d . . . . .
H5 H 0.8449 0.8719 0.6559 0.038 Uiso 1 1 calc R U . . .
C20 C 0.49007(17) 0.25380(13) 0.15476(13) 0.0309(4) Uani 1 1 d . . . . .
C15 C 0.5061(2) 0.15209(14) 0.11854(14) 0.0397(5) Uani 1 1 d . . . . .
H15 H 0.4430 0.0873 0.0694 0.048 Uiso 1 1 calc R U . . .
C32 C 0.65308(17) 0.90365(16) 0.20715(17) 0.0369(4) Uani 1 1 d . . . . .
H32 H 0.6170 0.9066 0.1430 0.044 Uiso 1 1 calc R U . . .
H32A H 0.5941 0.8553 0.2159 0.044 Uiso 1 1 calc R U . . .
C22 C 0.41377(17) 0.74636(17) 0.54343(14) 0.0366(4) Uani 1 1 d . . . . .
H22 H 0.3964 0.6693 0.5203 0.055 Uiso 1 1 calc R U . . .
H22A H 0.3439 0.7639 0.5426 0.055 Uiso 1 1 calc R U . . .
H22B H 0.4697 0.7905 0.6163 0.055 Uiso 1 1 calc R U . . .
C17 C 0.7047(2) 0.24092(16) 0.22406(16) 0.0388(4) Uani 1 1 d . . . . .
H17 H 0.7770 0.2358 0.2476 0.047 Uiso 1 1 calc R U . . .
C42 C 1.14769(17) 0.83378(16) 0.16816(16) 0.0339(4) Uani 1 1 d . . . . .
H42 H 1.1237 0.8866 0.1509 0.041 Uiso 1 1 calc R U . . .
C34 C 0.76178(18) 1.01805(16) 0.40522(17) 0.0392(4) Uani 1 1 d . . . . .
H34 H 0.7077 0.9749 0.4229 0.047 Uiso 1 1 calc R U . . .
H34A H 0.7949 1.0935 0.4665 0.047 Uiso 1 1 calc R U . . .
C16 C 0.6093(2) 0.14565(15) 0.15266(16) 0.0433(5) Uani 1 1 d . . . . .
H16 H 0.6178 0.0767 0.1285 0.052 Uiso 1 1 calc R U . . .
C33 C 0.69818(19) 1.01677(16) 0.30533(19) 0.0430(5) Uani 1 1 d . . . . .
H33 H 0.6338 1.0424 0.3167 0.052 Uiso 1 1 calc R U . . .
H33A H 0.7501 1.0671 0.2929 0.052 Uiso 1 1 calc R U . . .
C41 C 1.10753(18) 0.63767(17) 0.41044(16) 0.0385(4) Uani 1 1 d . . . . .
H41 H 1.0972 0.6969 0.4707 0.046 Uiso 1 1 calc R U . . .
H41A H 1.1781 0.6687 0.4005 0.046 Uiso 1 1 calc R U . . .
C37 C 1.01594(18) 0.49399(16) 0.21617(16) 0.0378(4) Uani 1 1 d . . . . .
H37 H 0.9474 0.4623 0.1519 0.045 Uiso 1 1 calc R U . . .
H37A H 1.0833 0.5185 0.1987 0.045 Uiso 1 1 calc R U . . .
C39 C 1.12856(19) 0.4538(2) 0.3459(2) 0.0477(5) Uani 1 1 d . . . . .
H39 H 1.1313 0.3971 0.3647 0.057 Uiso 1 1 calc R U . . .
H39A H 1.1998 0.4766 0.3328 0.057 Uiso 1 1 calc R U . . .
C47 C 1.14377(19) 0.74019(18) 0.06436(16) 0.0414(5) Uani 1 1 d . . . . .
H47 H 1.0651 0.7054 0.0123 0.050 Uiso 1 1 calc R U . . .
H47A H 1.1641 0.6853 0.0789 0.050 Uiso 1 1 calc R U . . .
C43 C 1.26898(19) 0.89178(19) 0.24687(17) 0.0461(5) Uani 1 1 d . . . . .
H43 H 1.2941 0.8419 0.2672 0.055 Uiso 1 1 calc R U . . .
H43A H 1.2716 0.9548 0.3127 0.055 Uiso 1 1 calc R U . . .
C46 C 1.2252(2) 0.7775(2) 0.01497(17) 0.0484(5) Uani 1 1 d . . . . .
H46 H 1.2240 0.7136 -0.0492 0.058 Uiso 1 1 calc R U . . .
H46A H 1.1992 0.8253 -0.0081 0.058 Uiso 1 1 calc R U . . .
C23 C 0.4873(2) 0.88463(18) 0.49262(18) 0.0477(5) Uani 1 1 d . . . . .
H23 H 0.4181 0.9032 0.4929 0.072 Uiso 1 1 calc R U . . .
H23A H 0.5137 0.8924 0.4379 0.072 Uiso 1 1 calc R U . . .
H23B H 0.5468 0.9334 0.5632 0.072 Uiso 1 1 calc R U . . .
C38 C 1.0270(2) 0.40743(17) 0.24466(19) 0.0456(5) Uani 1 1 d . . . . .
H38 H 0.9565 0.3780 0.2555 0.055 Uiso 1 1 calc R U . . .
H38A H 1.0363 0.3471 0.1845 0.055 Uiso 1 1 calc R U . . .
C45 C 1.34421(19) 0.83748(19) 0.09328(18) 0.0444(5) Uani 1 1 d . . . . .
H45 H 1.3932 0.8659 0.0611 0.053 Uiso 1 1 calc R U . . .
H45A H 1.3739 0.7866 0.1083 0.053 Uiso 1 1 calc R U . . .
C40 C 1.1201(2) 0.5500(2) 0.43813(19) 0.0489(5) Uani 1 1 d . . . . .
H40 H 1.1893 0.5816 0.5017 0.059 Uiso 1 1 calc R U . . .
H40A H 1.0536 0.5253 0.4565 0.059 Uiso 1 1 calc R U . . .
C44 C 1.3505(2) 0.9309(2) 0.19769(19) 0.0553(6) Uani 1 1 d . . . . .
H44 H 1.3303 0.9865 0.1844 0.066 Uiso 1 1 calc R U . . .
H44A H 1.4295 0.9647 0.2490 0.066 Uiso 1 1 calc R U . . .
H44B H 0.515(2) 0.395(2) -0.023(2) 0.056(8) Uiso 1 1 d . . . . .
H44C H 0.705(3) 0.490(3) -0.042(3) 0.109(13) 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
P1 O2 1.4915(11) . ?
P1 O4 1.5274(12) . ?
P1 O3 1.5551(13) . ?
P1 O1 1.5713(11) . ?
P2 O6 1.4660(14) . ?
P2 O8 1.5486(12) . ?
P2 O7 1.5487(15) . ?
P2 O5 1.5784(13) . ?
O1 C2 1.4019(16) . ?
O3 H44B 0.82(3) . ?
O5 C12 1.398(2) . ?
O8 C21 1.479(2) . ?
O4 H44C 0.98(4) . ?
C1 C2 1.373(2) . ?
C1 C9 1.433(2) . ?
C1 C11 1.494(2) . ?
C3 C4 1.375(2) . ?
C3 C2 1.419(2) . ?
C3 C24 1.500(2) . ?
C4 C10 1.411(2) . ?
C4 H4 0.9500 . ?
O7 H7A 0.89(3) . ?
C25 C26 1.400(2) . ?
C25 C24 1.410(2) . ?
C25 C30 1.511(2) . ?
C11 C12 1.366(2) . ?
C11 C19 1.430(2) . ?
C9 C10 1.417(2) . ?
C9 C8 1.418(2) . ?
C12 C13 1.409(2) . ?
C24 C29 1.403(2) . ?
C8 C7 1.372(2) . ?
C8 H8 0.9500 . ?
C19 C18 1.415(3) . ?
C19 C20 1.428(2) . ?
C10 C5 1.425(2) . ?
C29 C28 1.391(2) . ?
C29 C36 1.519(2) . ?
C18 C17 1.370(2) . ?
C18 H18 0.9500 . ?
C26 C27 1.382(2) . ?
C26 H26 0.9500 . ?
C28 C27 1.395(2) . ?
C28 H28 0.9500 . ?
C14 C13 1.366(3) . ?
C14 C20 1.410(3) . ?
C14 H14 0.9500 . ?
C30 C35 1.536(2) . ?
C30 C31 1.538(2) . ?
C30 H30 1.0000 . ?
C31 C32 1.530(3) . ?
C31 H31 0.9900 . ?
C31 H31A 0.9900 . ?
C21 C23 1.495(3) . ?
C21 C22 1.511(3) . ?
C21 H21 0.98(2) . ?
C36 C41 1.521(3) . ?
C36 C37 1.531(3) . ?
C36 H36 1.0000 . ?
C13 H13 0.9500 . ?
C6 C5 1.359(3) . ?
C6 C7 1.409(3) . ?
C6 H6 0.9500 . ?
C27 C42 1.520(2) . ?
C7 H7 0.9500 . ?
C35 C34 1.524(3) . ?
C35 H35 0.9900 . ?
C35 H35A 0.9900 . ?
C5 H5 0.9500 . ?
C20 C15 1.420(3) . ?
C15 C16 1.351(3) . ?
C15 H15 0.9500 . ?
C32 C33 1.520(3) . ?
C32 H32 0.9900 . ?
C32 H32A 0.9900 . ?
C22 H22 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C17 C16 1.411(3) . ?
C17 H17 0.9500 . ?
C42 C43 1.518(3) . ?
C42 C47 1.523(3) . ?
C42 H42 1.0000 . ?
C34 C33 1.523(3) . ?
C34 H34 0.9900 . ?
C34 H34A 0.9900 . ?
C16 H16 0.9500 . ?
C33 H33 0.9900 . ?
C33 H33A 0.9900 . ?
C41 C40 1.539(3) . ?
C41 H41 0.9900 . ?
C41 H41A 0.9900 . ?
C37 C38 1.526(3) . ?
C37 H37 0.9900 . ?
C37 H37A 0.9900 . ?
C39 C40 1.512(4) . ?
C39 C38 1.521(3) . ?
C39 H39 0.9900 . ?
C39 H39A 0.9900 . ?
C47 C46 1.531(3) . ?
C47 H47 0.9900 . ?
C47 H47A 0.9900 . ?
C43 C44 1.540(3) . ?
C43 H43 0.9900 . ?
C43 H43A 0.9900 . ?
C46 C45 1.495(3) . ?
C46 H46 0.9900 . ?
C46 H46A 0.9900 . ?
C23 H23 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C38 H38 0.9900 . ?
C38 H38A 0.9900 . ?
C45 C44 1.516(3) . ?
C45 H45 0.9900 . ?
C45 H45A 0.9900 . ?
C40 H40 0.9900 . ?
C40 H40A 0.9900 . ?
C44 H44 0.9900 . ?
C44 H44A 0.9900 . ?

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
O2 P1 O4 114.13(7) . . ?
O2 P1 O3 112.80(7) . . ?
O4 P1 O3 109.94(7) . . ?
O2 P1 O1 111.86(6) . . ?
O4 P1 O1 103.96(7) . . ?
O3 P1 O1 103.27(6) . . ?
O6 P2 O8 111.57(7) . . ?
O6 P2 O7 116.64(8) . . ?
O8 P2 O7 105.94(8) . . ?
O6 P2 O5 113.36(8) . . ?
O8 P2 O5 101.38(7) . . ?
O7 P2 O5 106.59(7) . . ?
C2 O1 P1 124.50(9) . . ?
P1 O3 H44B 112.3(19) . . ?
C12 O5 P2 128.32(10) . . ?
C21 O8 P2 120.84(11) . . ?
P1 O4 H44C 108(2) . . ?
C2 C1 C9 117.87(14) . . ?
C2 C1 C11 119.66(13) . . ?
C9 C1 C11 122.36(13) . . ?
C4 C3 C2 116.95(14) . . ?
C4 C3 C24 121.11(14) . . ?
C2 C3 C24 121.95(13) . . ?
C3 C4 C10 122.17(14) . . ?
C3 C4 H4 118.9 . . ?
C10 C4 H4 118.9 . . ?
P2 O7 H7A 114.5(19) . . ?
C1 C2 O1 118.69(13) . . ?
C1 C2 C3 124.10(13) . . ?
O1 C2 C3 117.12(13) . . ?
C26 C25 C24 118.42(15) . . ?
C26 C25 C30 119.30(14) . . ?
C24 C25 C30 122.28(14) . . ?
C12 C11 C19 117.79(15) . . ?
C12 C11 C1 120.55(14) . . ?
C19 C11 C1 121.66(14) . . ?
C10 C9 C8 118.56(13) . . ?
C10 C9 C1 119.38(14) . . ?
C8 C9 C1 122.06(14) . . ?
C11 C12 O5 118.25(14) . . ?
C11 C12 C13 123.13(16) . . ?
O5 C12 C13 118.30(15) . . ?
C29 C24 C25 120.52(14) . . ?
C29 C24 C3 119.61(14) . . ?
C25 C24 C3 119.82(14) . . ?
C7 C8 C9 120.77(15) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C18 C19 C20 118.43(16) . . ?
C18 C19 C11 121.94(15) . . ?
C20 C19 C11 119.57(16) . . ?
C4 C10 C9 119.44(14) . . ?
C4 C10 C5 121.49(15) . . ?
C9 C10 C5 119.07(15) . . ?
C28 C29 C24 118.59(15) . . ?
C28 C29 C36 119.53(15) . . ?
C24 C29 C36 121.85(14) . . ?
C17 C18 C19 120.94(18) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C27 C26 C25 122.07(15) . . ?
C27 C26 H26 119.0 . . ?
C25 C26 H26 119.0 . . ?
C29 C28 C27 122.13(16) . . ?
C29 C28 H28 118.9 . . ?
C27 C28 H28 118.9 . . ?
C13 C14 C20 120.81(16) . . ?
C13 C14 H14 119.6 . . ?
C20 C14 H14 119.6 . . ?
C25 C30 C35 112.50(14) . . ?
C25 C30 C31 112.61(13) . . ?
C35 C30 C31 109.65(13) . . ?
C25 C30 H30 107.3 . . ?
C35 C30 H30 107.3 . . ?
C31 C30 H30 107.3 . . ?
C32 C31 C30 111.02(15) . . ?
C32 C31 H31 109.4 . . ?
C30 C31 H31 109.4 . . ?
C32 C31 H31A 109.4 . . ?
C30 C31 H31A 109.4 . . ?
H31 C31 H31A 108.0 . . ?
O8 C21 C23 106.05(16) . . ?
O8 C21 C22 107.58(15) . . ?
C23 C21 C22 114.30(16) . . ?
O8 C21 H21 107.6(14) . . ?
C23 C21 H21 106.9(14) . . ?
C22 C21 H21 114.0(14) . . ?
C29 C36 C41 110.90(15) . . ?
C29 C36 C37 112.35(15) . . ?
C41 C36 C37 110.44(15) . . ?
C29 C36 H36 107.6 . . ?
C41 C36 H36 107.6 . . ?
C37 C36 H36 107.6 . . ?
C14 C13 C12 119.03(18) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C5 C6 C7 120.11(15) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C26 C27 C28 118.24(15) . . ?
C26 C27 C42 120.19(15) . . ?
C28 C27 C42 121.55(16) . . ?
C8 C7 C6 120.50(16) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C34 C35 C30 111.66(15) . . ?
C34 C35 H35 109.3 . . ?
C30 C35 H35 109.3 . . ?
C34 C35 H35A 109.3 . . ?
C30 C35 H35A 109.3 . . ?
H35 C35 H35A 107.9 . . ?
C6 C5 C10 120.91(16) . . ?
C6 C5 H5 119.5 . . ?
C10 C5 H5 119.5 . . ?
C14 C20 C15 122.09(17) . . ?
C14 C20 C19 119.16(16) . . ?
C15 C20 C19 118.73(18) . . ?
C16 C15 C20 121.28(18) . . ?
C16 C15 H15 119.4 . . ?
C20 C15 H15 119.4 . . ?
C33 C32 C31 111.59(16) . . ?
C33 C32 H32 109.3 . . ?
C31 C32 H32 109.3 . . ?
C33 C32 H32A 109.3 . . ?
C31 C32 H32A 109.3 . . ?
H32 C32 H32A 108.0 . . ?
C21 C22 H22 109.5 . . ?
C21 C22 H22A 109.5 . . ?
H22 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C43 C42 C27 111.70(16) . . ?
C43 C42 C47 109.88(16) . . ?
C27 C42 C47 111.91(16) . . ?
C43 C42 H42 107.7 . . ?
C27 C42 H42 107.7 . . ?
C47 C42 H42 107.7 . . ?
C33 C34 C35 111.06(16) . . ?
C33 C34 H34 109.4 . . ?
C35 C34 H34 109.4 . . ?
C33 C34 H34A 109.4 . . ?
C35 C34 H34A 109.4 . . ?
H34 C34 H34A 108.0 . . ?
C15 C16 C17 120.29(18) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C32 C33 C34 111.43(16) . . ?
C32 C33 H33 109.3 . . ?
C34 C33 H33 109.3 . . ?
C32 C33 H33A 109.3 . . ?
C34 C33 H33A 109.3 . . ?
H33 C33 H33A 108.0 . . ?
C36 C41 C40 111.41(17) . . ?
C36 C41 H41 109.3 . . ?
C40 C41 H41 109.3 . . ?
C36 C41 H41A 109.3 . . ?
C40 C41 H41A 109.3 . . ?
H41 C41 H41A 108.0 . . ?
C38 C37 C36 111.31(17) . . ?
C38 C37 H37 109.4 . . ?
C36 C37 H37 109.4 . . ?
C38 C37 H37A 109.4 . . ?
C36 C37 H37A 109.4 . . ?
H37 C37 H37A 108.0 . . ?
C40 C39 C38 110.75(17) . . ?
C40 C39 H39 109.5 . . ?
C38 C39 H39 109.5 . . ?
C40 C39 H39A 109.5 . . ?
C38 C39 H39A 109.5 . . ?
H39 C39 H39A 108.1 . . ?
C42 C47 C46 112.19(17) . . ?
C42 C47 H47 109.2 . . ?
C46 C47 H47 109.2 . . ?
C42 C47 H47A 109.2 . . ?
C46 C47 H47A 109.2 . . ?
H47 C47 H47A 107.9 . . ?
C42 C43 C44 111.02(19) . . ?
C42 C43 H43 109.4 . . ?
C44 C43 H43 109.4 . . ?
C42 C43 H43A 109.4 . . ?
C44 C43 H43A 109.4 . . ?
H43 C43 H43A 108.0 . . ?
C45 C46 C47 111.26(18) . . ?
C45 C46 H46 109.4 . . ?
C47 C46 H46 109.4 . . ?
C45 C46 H46A 109.4 . . ?
C47 C46 H46A 109.4 . . ?
H46 C46 H46A 108.0 . . ?
C21 C23 H23 109.5 . . ?
C21 C23 H23A 109.5 . . ?
H23 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C39 C38 C37 111.20(18) . . ?
C39 C38 H38 109.4 . . ?
C37 C38 H38 109.4 . . ?
C39 C38 H38A 109.4 . . ?
C37 C38 H38A 109.4 . . ?
H38 C38 H38A 108.0 . . ?
C46 C45 C44 112.11(19) . . ?
C46 C45 H45 109.2 . . ?
C44 C45 H45 109.2 . . ?
C46 C45 H45A 109.2 . . ?
C44 C45 H45A 109.2 . . ?
H45 C45 H45A 107.9 . . ?
C39 C40 C41 111.73(17) . . ?
C39 C40 H40 109.3 . . ?
C41 C40 H40 109.3 . . ?
C39 C40 H40A 109.3 . . ?
C41 C40 H40A 109.3 . . ?
H40 C40 H40A 107.9 . . ?
C45 C44 C43 111.11(19) . . ?
C45 C44 H44 109.4 . . ?
C43 C44 H44 109.4 . . ?
C45 C44 H44A 109.4 . . ?
C43 C44 H44A 109.4 . . ?
H44 C44 H44A 108.0 . . ?

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
O2 P1 O1 C2 -1.23(13) . . . . ?
O4 P1 O1 C2 122.38(12) . . . . ?
O3 P1 O1 C2 -122.81(12) . . . . ?
O6 P2 O5 C12 49.44(15) . . . . ?
O8 P2 O5 C12 169.14(13) . . . . ?
O7 P2 O5 C12 -80.23(15) . . . . ?
O6 P2 O8 C21 -179.54(14) . . . . ?
O7 P2 O8 C21 -51.64(15) . . . . ?
O5 P2 O8 C21 59.49(15) . . . . ?
C2 C3 C4 C10 1.3(2) . . . . ?
C24 C3 C4 C10 -179.12(14) . . . . ?
C9 C1 C2 O1 175.46(13) . . . . ?
C11 C1 C2 O1 -8.3(2) . . . . ?
C9 C1 C2 C3 -0.9(2) . . . . ?
C11 C1 C2 C3 175.33(14) . . . . ?
P1 O1 C2 C1 93.10(15) . . . . ?
P1 O1 C2 C3 -90.28(15) . . . . ?
C4 C3 C2 C1 -1.3(2) . . . . ?
C24 C3 C2 C1 179.12(14) . . . . ?
C4 C3 C2 O1 -177.74(13) . . . . ?
C24 C3 C2 O1 2.7(2) . . . . ?
C2 C1 C11 C12 -108.20(17) . . . . ?
C9 C1 C11 C12 67.9(2) . . . . ?
C2 C1 C11 C19 70.88(19) . . . . ?
C9 C1 C11 C19 -113.07(17) . . . . ?
C2 C1 C9 C10 3.1(2) . . . . ?
C11 C1 C9 C10 -172.98(14) . . . . ?
C2 C1 C9 C8 -177.26(14) . . . . ?
C11 C1 C9 C8 6.6(2) . . . . ?
C19 C11 C12 O5 165.69(13) . . . . ?
C1 C11 C12 O5 -15.2(2) . . . . ?
C19 C11 C12 C13 -7.8(2) . . . . ?
C1 C11 C12 C13 171.33(14) . . . . ?
P2 O5 C12 C11 113.33(15) . . . . ?
P2 O5 C12 C13 -72.88(19) . . . . ?
C26 C25 C24 C29 -1.7(2) . . . . ?
C30 C25 C24 C29 177.93(15) . . . . ?
C26 C25 C24 C3 175.79(14) . . . . ?
C30 C25 C24 C3 -4.6(2) . . . . ?
C4 C3 C24 C29 104.93(18) . . . . ?
C2 C3 C24 C29 -75.53(19) . . . . ?
C4 C3 C24 C25 -72.6(2) . . . . ?
C2 C3 C24 C25 106.95(17) . . . . ?
C10 C9 C8 C7 2.1(2) . . . . ?
C1 C9 C8 C7 -177.48(16) . . . . ?
C12 C11 C19 C18 -172.94(14) . . . . ?
C1 C11 C19 C18 8.0(2) . . . . ?
C12 C11 C19 C20 4.2(2) . . . . ?
C1 C11 C19 C20 -174.94(13) . . . . ?
C3 C4 C10 C9 0.9(2) . . . . ?
C3 C4 C10 C5 -178.47(16) . . . . ?
C8 C9 C10 C4 177.21(15) . . . . ?
C1 C9 C10 C4 -3.2(2) . . . . ?
C8 C9 C10 C5 -3.4(2) . . . . ?
C1 C9 C10 C5 176.22(15) . . . . ?
C25 C24 C29 C28 2.0(2) . . . . ?
C3 C24 C29 C28 -175.56(15) . . . . ?
C25 C24 C29 C36 -179.83(15) . . . . ?
C3 C24 C29 C36 2.7(2) . . . . ?
C20 C19 C18 C17 -2.0(2) . . . . ?
C11 C19 C18 C17 175.16(15) . . . . ?
C24 C25 C26 C27 0.9(3) . . . . ?
C30 C25 C26 C27 -178.78(16) . . . . ?
C24 C29 C28 C27 -1.4(3) . . . . ?
C36 C29 C28 C27 -179.63(16) . . . . ?
C26 C25 C30 C35 -75.39(19) . . . . ?
C24 C25 C30 C35 104.97(17) . . . . ?
C26 C25 C30 C31 49.1(2) . . . . ?
C24 C25 C30 C31 -130.50(16) . . . . ?
C25 C30 C31 C32 177.76(14) . . . . ?
C35 C30 C31 C32 -56.16(19) . . . . ?
P2 O8 C21 C23 111.45(16) . . . . ?
P2 O8 C21 C22 -125.84(14) . . . . ?
C28 C29 C36 C41 73.8(2) . . . . ?
C24 C29 C36 C41 -104.39(18) . . . . ?
C28 C29 C36 C37 -50.3(2) . . . . ?
C24 C29 C36 C37 131.48(17) . . . . ?
C20 C14 C13 C12 2.1(3) . . . . ?
C11 C12 C13 C14 4.8(3) . . . . ?
O5 C12 C13 C14 -168.69(15) . . . . ?
C25 C26 C27 C28 -0.3(3) . . . . ?
C25 C26 C27 C42 178.38(17) . . . . ?
C29 C28 C27 C26 0.5(3) . . . . ?
C29 C28 C27 C42 -178.11(17) . . . . ?
C9 C8 C7 C6 0.4(3) . . . . ?
C5 C6 C7 C8 -1.7(3) . . . . ?
C25 C30 C35 C34 -177.22(15) . . . . ?
C31 C30 C35 C34 56.64(19) . . . . ?
C7 C6 C5 C10 0.3(3) . . . . ?
C4 C10 C5 C6 -178.39(18) . . . . ?
C9 C10 C5 C6 2.2(3) . . . . ?
C13 C14 C20 C15 173.05(17) . . . . ?
C13 C14 C20 C19 -5.3(2) . . . . ?
C18 C19 C20 C14 179.39(15) . . . . ?
C11 C19 C20 C14 2.2(2) . . . . ?
C18 C19 C20 C15 0.9(2) . . . . ?
C11 C19 C20 C15 -176.28(14) . . . . ?
C14 C20 C15 C16 -177.76(17) . . . . ?
C19 C20 C15 C16 0.7(3) . . . . ?
C30 C31 C32 C33 56.1(2) . . . . ?
C19 C18 C17 C16 1.4(3) . . . . ?
C26 C27 C42 C43 114.7(2) . . . . ?
C28 C27 C42 C43 -66.7(2) . . . . ?
C26 C27 C42 C47 -121.62(19) . . . . ?
C28 C27 C42 C47 57.0(2) . . . . ?
C30 C35 C34 C33 -56.3(2) . . . . ?
C20 C15 C16 C17 -1.2(3) . . . . ?
C18 C17 C16 C15 0.2(3) . . . . ?
C31 C32 C33 C34 -55.1(2) . . . . ?
C35 C34 C33 C32 54.9(2) . . . . ?
C29 C36 C41 C40 -179.98(16) . . . . ?
C37 C36 C41 C40 -54.8(2) . . . . ?
C29 C36 C37 C38 -179.83(16) . . . . ?
C41 C36 C37 C38 55.8(2) . . . . ?
C43 C42 C47 C46 -55.9(2) . . . . ?
C27 C42 C47 C46 179.40(18) . . . . ?
C27 C42 C43 C44 -179.04(18) . . . . ?
C47 C42 C43 C44 56.1(2) . . . . ?
C42 C47 C46 C45 55.0(3) . . . . ?
C40 C39 C38 C37 56.1(2) . . . . ?
C36 C37 C38 C39 -56.6(2) . . . . ?
C47 C46 C45 C44 -54.0(3) . . . . ?
C38 C39 C40 C41 -55.4(2) . . . . ?
C36 C41 C40 C39 55.3(2) . . . . ?
C46 C45 C44 C43 54.8(3) . . . . ?
C42 C43 C44 C45 -56.0(3) . . . . ?

_refine_diff_density_max         0.736
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.064

_shelxl_version_number           2014/6

