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

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

data_sav4
_database_code_depnum_ccdc_archive 'CCDC 1491786'
_audit_update_record             
;
2016-07-09 deposited with the CCDC.
2016-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H30 N6 O6, 2 (C2 H3 N)'
_chemical_formula_sum            'C34 H36 N8 O6'
_chemical_formula_weight         652.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0010 0.0000 '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 -0.0010 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0010 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.717(6)
_cell_length_b                   17.333(9)
_cell_length_c                   8.824(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.290(6)
_cell_angle_gamma                90
_cell_volume                     1720.1(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15254
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      12.184
_cell_measurement_theta_min      0.896

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.056
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.2952
_diffrn_radiation_type           Synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'ESRF ID11 beamline goniometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15254
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         0.896
_diffrn_reflns_theta_max         12.184
_diffrn_reflns_theta_full        10.202
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measured_fraction_theta_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_point_group_measured_fraction_full 0.955
_reflns_number_total             4708
_reflns_number_gt                4038
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1511P)²+0.2247P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4708
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.2189
_refine_ls_wR_factor_gt          0.2034
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_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
O1 O 0.46593(10) 0.70652(7) 0.71729(13) 0.0209(3) Uani 1 1 d . . . . .
O2 O 0.35855(10) 0.52030(7) 0.50720(12) 0.0197(3) Uani 1 1 d . . . . .
O3 O 0.19152(11) 0.34976(8) 0.22582(15) 0.0261(3) Uani 1 1 d . . . . .
N1 N 0.31552(12) 0.67430(8) 0.50084(15) 0.0193(3) Uani 1 1 d . . . . .
N2 N 0.28926(12) 0.50284(7) 0.24338(14) 0.0168(3) Uani 1 1 d . . . . .
N3 N 0.35598(12) 0.31753(8) 0.42163(15) 0.0193(3) Uani 1 1 d . . . . .
C1 C 0.43173(14) 0.68438(8) 0.57934(17) 0.0171(3) Uani 1 1 d . . . . .
C2 C 0.27715(14) 0.63292(9) 0.35186(17) 0.0198(3) Uani 1 1 d . . . . .
H2A H 0.3159 0.6555 0.2759 0.024 Uiso 1 1 calc R U . . .
H2B H 0.1901 0.6385 0.3074 0.024 Uiso 1 1 calc R U . . .
C3 C 0.22597(15) 0.68317(10) 0.58839(19) 0.0224(3) Uani 1 1 d . . . . .
H3A H 0.1914 0.6321 0.5994 0.027 Uiso 1 1 calc R U . . .
H3B H 0.2652 0.7029 0.6957 0.027 Uiso 1 1 calc R U . . .
C4 C 0.13053(15) 0.73617(11) 0.5086(2) 0.0268(4) Uani 1 1 d . . . . .
C5 C 0.05156(17) 0.77872(13) 0.4458(3) 0.0366(5) Uani 1 1 d . . . . .
H5 H -0.0114 0.8126 0.3957 0.044 Uiso 1 1 calc R U . . .
C6 C 0.30905(13) 0.54674(9) 0.37479(16) 0.0166(3) Uani 1 1 d . . . . .
C7 C 0.35880(13) 0.43188(8) 0.25509(16) 0.0167(3) Uani 1 1 d . . . . .
H7A H 0.4365 0.4389 0.3350 0.020 Uiso 1 1 calc R U . . .
H7B H 0.3742 0.4215 0.1523 0.020 Uiso 1 1 calc R U . . .
C8 C 0.21990(14) 0.52833(9) 0.08524(16) 0.0189(3) Uani 1 1 d . . . . .
H8A H 0.1782 0.4835 0.0251 0.023 Uiso 1 1 calc R U . . .
H8B H 0.1590 0.5660 0.0956 0.023 Uiso 1 1 calc R U . . .
C9 C 0.29605(16) 0.56395(10) -0.00182(19) 0.0243(3) Uani 1 1 d . . . . .
C10 C 0.36338(18) 0.59351(13) -0.0639(2) 0.0359(5) Uani 1 1 d . . . . .
H10 H 0.4169 0.6170 -0.1132 0.043 Uiso 1 1 calc R U . . .
C11 C 0.29513(13) 0.36301(9) 0.30075(17) 0.0178(3) Uani 1 1 d . . . . .
C12 C 0.47820(13) 0.33248(9) 0.51394(16) 0.0181(3) Uani 1 1 d . . . . .
H12A H 0.4972 0.3000 0.6101 0.022 Uiso 1 1 calc R U . . .
H12B H 0.4856 0.3872 0.5477 0.022 Uiso 1 1 calc R U . . .
C13 C 0.29904(16) 0.24687(9) 0.4562(2) 0.0244(3) Uani 1 1 d . . . . .
H13A H 0.2117 0.2531 0.4177 0.029 Uiso 1 1 calc R U . . .
H13B H 0.3202 0.2396 0.5720 0.029 Uiso 1 1 calc R U . . .
C14 C 0.33354(16) 0.17727(10) 0.3838(2) 0.0248(3) Uani 1 1 d . . . . .
C15 C 0.35981(19) 0.11952(11) 0.3282(2) 0.0323(4) Uani 1 1 d . . . . .
H15 H 0.3807 0.0735 0.2839 0.039 Uiso 1 1 calc R U . . .
N4 N 0.0038(2) 0.44666(17) 0.7376(3) 0.0562(6) Uani 1 1 d . . . . .
C16 C 0.04961(19) 0.42685(15) 0.6458(3) 0.0403(5) Uani 1 1 d . . . . .
C17 C 0.1073(2) 0.40141(17) 0.5284(3) 0.0465(6) Uani 1 1 d . . . . .
H17A H 0.1317 0.3474 0.5481 0.070 Uiso 1 1 calc R U . . .
H17B H 0.1774 0.4335 0.5351 0.070 Uiso 1 1 calc R U . . .
H17C H 0.0516 0.4062 0.4227 0.070 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
O1 C1 1.2312(19) . ?
O2 C6 1.2375(18) . ?
O3 C11 1.230(2) . ?
N1 C1 1.355(2) . ?
N1 C2 1.4536(19) . ?
N1 C3 1.475(2) . ?
N2 C6 1.3514(19) . ?
N2 C7 1.463(2) . ?
N2 C8 1.4720(19) . ?
N3 C11 1.357(2) . ?
N3 C12 1.458(2) . ?
N3 C13 1.467(2) . ?
C1 C12 1.538(2) 3_666 ?
C2 C6 1.539(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.466(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.191(3) . ?
C5 H5 0.9500 . ?
C7 C11 1.521(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.467(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.195(3) . ?
C10 H10 0.9500 . ?
C12 C1 1.538(2) 3_666 ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.474(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.192(3) . ?
C15 H15 0.9500 . ?
N4 C16 1.143(3) . ?
C16 C17 1.455(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 122.52(13) . . ?
C1 N1 C3 118.64(13) . . ?
C2 N1 C3 116.10(13) . . ?
C6 N2 C7 117.04(12) . . ?
C6 N2 C8 124.10(13) . . ?
C7 N2 C8 117.89(12) . . ?
C11 N3 C12 123.57(13) . . ?
C11 N3 C13 118.63(13) . . ?
C12 N3 C13 117.69(13) . . ?
O1 C1 N1 123.20(15) . . ?
O1 C1 C12 120.43(14) . 3_666 ?
N1 C1 C12 116.37(13) . 3_666 ?
N1 C2 C6 110.97(12) . . ?
N1 C2 H2A 109.4 . . ?
C6 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C6 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 N1 111.88(14) . . ?
C4 C3 H3A 109.2 . . ?
N1 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
N1 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 178.6(2) . . ?
C4 C5 H5 180.0 . . ?
O2 C6 N2 121.58(14) . . ?
O2 C6 C2 121.04(13) . . ?
N2 C6 C2 117.18(12) . . ?
N2 C7 C11 111.95(13) . . ?
N2 C7 H7A 109.2 . . ?
C11 C7 H7A 109.2 . . ?
N2 C7 H7B 109.2 . . ?
C11 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 N2 111.57(13) . . ?
C9 C8 H8A 109.3 . . ?
N2 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
N2 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 175.89(18) . . ?
C9 C10 H10 180.0 . . ?
O3 C11 N3 122.40(14) . . ?
O3 C11 C7 119.19(14) . . ?
N3 C11 C7 118.40(13) . . ?
N3 C12 C1 112.41(12) . 3_666 ?
N3 C12 H12A 109.1 . . ?
C1 C12 H12A 109.1 3_666 . ?
N3 C12 H12B 109.1 . . ?
C1 C12 H12B 109.1 3_666 . ?
H12A C12 H12B 107.9 . . ?
N3 C13 C14 113.40(14) . . ?
N3 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
N3 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 177.87(18) . . ?
C14 C15 H15 180.0 . . ?
N4 C16 C17 179.7(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 O1 -166.41(14) . . . . ?
C3 N1 C1 O1 -5.9(2) . . . . ?
C2 N1 C1 C12 14.3(2) . . . 3_666 ?
C3 N1 C1 C12 174.83(12) . . . 3_666 ?
C1 N1 C2 C6 67.08(19) . . . . ?
C3 N1 C2 C6 -93.90(15) . . . . ?
C1 N1 C3 C4 128.60(15) . . . . ?
C2 N1 C3 C4 -69.65(18) . . . . ?
C7 N2 C6 O2 -18.3(2) . . . . ?
C8 N2 C6 O2 173.25(14) . . . . ?
C7 N2 C6 C2 156.64(13) . . . . ?
C8 N2 C6 C2 -11.8(2) . . . . ?
N1 C2 C6 O2 1.4(2) . . . . ?
N1 C2 C6 N2 -173.51(13) . . . . ?
C6 N2 C7 C11 91.63(16) . . . . ?
C8 N2 C7 C11 -99.16(15) . . . . ?
C6 N2 C8 C9 91.72(19) . . . . ?
C7 N2 C8 C9 -76.66(17) . . . . ?
C12 N3 C11 O3 -179.07(14) . . . . ?
C13 N3 C11 O3 4.7(2) . . . . ?
C12 N3 C11 C7 2.1(2) . . . . ?
C13 N3 C11 C7 -174.11(13) . . . . ?
N2 C7 C11 O3 51.02(19) . . . . ?
N2 C7 C11 N3 -130.11(14) . . . . ?
C11 N3 C12 C1 -72.39(19) . . . 3_666 ?
C13 N3 C12 C1 103.85(15) . . . 3_666 ?
C11 N3 C13 C14 96.56(18) . . . . ?
C12 N3 C13 C14 -79.88(18) . . . . ?

_refine_diff_density_max         0.591
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.093


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_ale26_31_1
_database_code_depnum_ccdc_archive 'CCDC 1491787'
_audit_update_record             
;
2016-07-09 deposited with the CCDC.
2016-09-23 downloaded from the CCDC.
;
_audit_creation_date             2016-05-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H30 N6 O6, 2(O H2), 2(C2 H6 O S)'
_chemical_formula_sum            'C34 H46 N6 O10 S2'
_chemical_formula_weight         762.89
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.022(2)
_cell_length_b                   17.377(3)
_cell_length_c                   8.6788(15)
_cell_angle_alpha                90
_cell_angle_beta                 102.255(4)
_cell_angle_gamma                90
_cell_volume                     1919.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(5)
_cell_measurement_reflns_used    4993
_cell_measurement_theta_min      1.6001
_cell_measurement_theta_max      28.3389
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'hexagonal plate'
_exptl_crystal_F_000             808
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile/water/DMSO'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1135
_diffrn_reflns_av_unetI/netI     0.1515
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15304
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.519
_diffrn_reflns_theta_min         1.600
_diffrn_ambient_temperature      100.0(5)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_detector_type            'Rigaku Mercury2'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       AFC7S
_diffrn_measurement_device_type  Rigaku_AFC7_Mo
_diffrn_measurement_method       dtprofit.ref
_diffrn_measurement_specimen_support 'Mitegen 150um'
_diffrn_radiation_collimation    0.5
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_target            Mo
_diffrn_source_type              'Sealed Tube'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2202
_reflns_number_total             4720
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_solution    'SIR2014 (Burla et al., 2015)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_refine_diff_density_max         0.937
_refine_diff_density_min         -1.119
_refine_diff_density_rms         0.210
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4720
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1987
_refine_ls_R_factor_gt           0.1145
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2724
_refine_ls_wR_factor_ref         0.3630
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C13(H13A,H13B), C7(H7A,H7B), C12(H12A,H12B), C8(H8A,
 H8B)
2.b Idealised Me refined as rotating group:
 C1S(H2S,H3S,H1S), C2S(H5S,H4S,H6S)
2.c :
 C5(H5), C10(H10), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group

O1 O 0.4527(3) 0.71102(19) 0.7130(3) 0.0295(8) Uani 1 1 d . . . . .
O2 O 0.3699(2) 0.50877(18) 0.5193(3) 0.0274(8) Uani 1 1 d . . . . .
O3 O 0.2356(3) 0.33698(18) 0.2773(4) 0.0297(8) Uani 1 1 d . . . . .
N1 N 0.3227(3) 0.6620(2) 0.5237(4) 0.0250(9) Uani 1 1 d . . . . .
N2 N 0.3088(3) 0.4937(2) 0.2585(4) 0.0255(9) Uani 1 1 d . . . . .
N3 N 0.3907(3) 0.3153(2) 0.4460(4) 0.0259(9) Uani 1 1 d . . . . .
C1 C 0.4237(4) 0.6799(2) 0.5817(5) 0.0246(10) Uani 1 1 d . . . . .
C2 C 0.2883(4) 0.6196(3) 0.3748(5) 0.0254(10) Uani 1 1 d . . . . .
H2A H 0.3181 0.6443 0.2913 0.030 Uiso 1 1 calc R . . . .
H2B H 0.2108 0.6218 0.3423 0.030 Uiso 1 1 calc R . . . .
C3 C 0.2427(4) 0.6782(3) 0.6141(5) 0.0287(10) Uani 1 1 d . . . . .
H3A H 0.2772 0.6910 0.7241 0.034 Uiso 1 1 calc R . . . .
H3B H 0.1991 0.6317 0.6164 0.034 Uiso 1 1 calc R . . . .
C4 C 0.1752(4) 0.7422(3) 0.5456(5) 0.0316(11) Uani 1 1 d . . . . .
C5 C 0.1223(4) 0.7947(3) 0.4862(6) 0.0351(12) Uani 1 1 d . . . . .
H5 H 0.0802 0.8365 0.4389 0.042 Uiso 1 1 calc R . . . .
C6 C 0.3234(3) 0.5364(2) 0.3929(5) 0.0228(9) Uani 1 1 d . . . . .
C7 C 0.3737(4) 0.4253(2) 0.2625(5) 0.0260(10) Uani 1 1 d . . . . .
H7A H 0.4445 0.4359 0.3271 0.031 Uiso 1 1 calc R . . . .
H7B H 0.3814 0.4131 0.1541 0.031 Uiso 1 1 calc R . . . .
C8 C 0.2532(4) 0.5231(3) 0.1036(5) 0.0280(11) Uani 1 1 d . . . . .
H8A H 0.2187 0.4797 0.0385 0.034 Uiso 1 1 calc R . . . .
H8B H 0.1978 0.5596 0.1186 0.034 Uiso 1 1 calc R . . . .
C9 C 0.3255(4) 0.5616(3) 0.0218(5) 0.0306(11) Uani 1 1 d . . . . .
C10 C 0.3868(4) 0.5931(3) -0.0399(6) 0.0413(13) Uani 1 1 d . . . . .
H10 H 0.4359 0.6184 -0.0893 0.050 Uiso 1 1 calc R . . . .
C11 C 0.3272(4) 0.3567(2) 0.3298(5) 0.0242(10) Uani 1 1 d . . . . .
C12 C 0.5022(3) 0.6623(3) 0.4808(5) 0.0240(10) Uani 1 1 d . . . . .
H12A H 0.5008 0.6064 0.4587 0.029 Uiso 1 1 calc R . . . .
H12B H 0.4808 0.6895 0.3788 0.029 Uiso 1 1 calc R . . . .
C13 C 0.3482(4) 0.2436(3) 0.4956(5) 0.0266(10) Uani 1 1 d . . . . .
H13A H 0.3882 0.2302 0.6024 0.032 Uiso 1 1 calc R . . . .
H13B H 0.2743 0.2525 0.5028 0.032 Uiso 1 1 calc R . . . .
C14 C 0.3517(4) 0.1781(3) 0.3909(5) 0.0270(10) Uani 1 1 d . . . . .
C15 C 0.3545(4) 0.1233(3) 0.3110(6) 0.0344(12) Uani 1 1 d . . . . .
H15 H 0.3567 0.0793 0.2468 0.041 Uiso 1 1 calc R . . . .
S1S S 0.06739(10) 0.41417(8) 0.73311(14) 0.0369(4) Uani 1 1 d . . . . .
O1S O -0.0456(3) 0.4411(2) 0.7120(4) 0.0424(9) Uani 1 1 d . . . . .
C1S C 0.0820(6) 0.3943(4) 0.5398(7) 0.0581(18) Uani 1 1 d . . . . .
H2S H 0.0197 0.3670 0.4823 0.087 Uiso 1 1 calc GR . . . .
H3S H 0.1443 0.3621 0.5439 0.087 Uiso 1 1 calc GR . . . .
H1S H 0.0903 0.4426 0.4856 0.087 Uiso 1 1 calc GR . . . .
C2S C 0.0719(4) 0.3175(3) 0.7988(6) 0.0410(13) Uani 1 1 d . . . . .
H5S H 0.0721 0.3164 0.9118 0.061 Uiso 1 1 calc GR . . . .
H4S H 0.1358 0.2928 0.7803 0.061 Uiso 1 1 calc GR . . . .
H6S H 0.0102 0.2897 0.7407 0.061 Uiso 1 1 calc GR . . . .
O2S O 0.0503(3) 0.4165(2) 0.1338(4) 0.0411(9) Uani 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
O2 C6 1.232(5) . ?
O1 C1 1.245(5) . ?
O3 C11 1.232(5) . ?
N3 C11 1.365(5) . ?
N3 C13 1.464(6) . ?
N3 C12 1.457(6) 3_666 ?
N2 C6 1.361(5) . ?
N2 C7 1.454(6) . ?
N2 C8 1.476(5) . ?
N1 C1 1.341(6) . ?
N1 C2 1.472(5) . ?
N1 C3 1.459(6) . ?
C11 C7 1.510(6) . ?
C1 C12 1.512(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C6 1.514(6) . ?
C14 C13 1.463(6) . ?
C14 C15 1.183(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.464(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C9 C8 1.457(7) . ?
C9 C10 1.185(8) . ?
C4 C5 1.192(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C12 N3 1.457(6) 3_666 ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C5 H5 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 H10 0.9500 . ?
C15 H15 0.9500 . ?
S1S O1S 1.517(4) . ?
S1S C1S 1.763(6) . ?
S1S C2S 1.772(6) . ?
C1S H2S 0.9800 . ?
C1S H3S 0.9800 . ?
C1S H1S 0.9800 . ?
C2S H5S 0.9800 . ?
C2S H4S 0.9800 . ?
C2S H6S 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N3 C13 117.3(4) . . ?
C11 N3 C12 123.6(4) . 3_666 ?
C12 N3 C13 119.1(3) 3_666 . ?
C6 N2 C7 116.8(3) . . ?
C6 N2 C8 123.0(4) . . ?
C7 N2 C8 118.3(4) . . ?
C1 N1 C2 122.5(4) . . ?
C1 N1 C3 120.6(4) . . ?
C3 N1 C2 116.7(4) . . ?
O3 C11 N3 120.9(4) . . ?
O3 C11 C7 120.8(4) . . ?
N3 C11 C7 118.2(4) . . ?
O1 C1 N1 121.8(4) . . ?
O1 C1 C12 120.4(4) . . ?
N1 C1 C12 117.8(4) . . ?
N1 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
N1 C2 C6 111.0(3) . . ?
H2A C2 H2B 108.0 . . ?
C6 C2 H2A 109.4 . . ?
C6 C2 H2B 109.4 . . ?
C15 C14 C13 177.4(5) . . ?
N1 C3 H3A 109.4 . . ?
N1 C3 H3B 109.4 . . ?
N1 C3 C4 111.4(4) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
N3 C13 H13A 108.6 . . ?
N3 C13 H13B 108.6 . . ?
C14 C13 N3 114.6(4) . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C10 C9 C8 177.7(5) . . ?
O2 C6 N2 120.2(4) . . ?
O2 C6 C2 123.0(4) . . ?
N2 C6 C2 116.6(4) . . ?
C5 C4 C3 177.8(6) . . ?
N2 C7 C11 112.1(4) . . ?
N2 C7 H7A 109.2 . . ?
N2 C7 H7B 109.2 . . ?
C11 C7 H7A 109.2 . . ?
C11 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N3 C12 C1 113.3(3) 3_666 . ?
N3 C12 H12A 108.9 3_666 . ?
N3 C12 H12B 108.9 3_666 . ?
C1 C12 H12A 108.9 . . ?
C1 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C4 C5 H5 180.0 . . ?
N2 C8 H8A 109.4 . . ?
N2 C8 H8B 109.4 . . ?
C9 C8 N2 111.0(4) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C9 C10 H10 180.0 . . ?
C14 C15 H15 180.0 . . ?
O1S S1S C1S 104.1(3) . . ?
O1S S1S C2S 107.2(2) . . ?
C1S S1S C2S 96.7(3) . . ?
S1S C1S H2S 109.5 . . ?
S1S C1S H3S 109.5 . . ?
S1S C1S H1S 109.5 . . ?
H2S C1S H3S 109.5 . . ?
H2S C1S H1S 109.5 . . ?
H3S C1S H1S 109.5 . . ?
S1S C2S H5S 109.5 . . ?
S1S C2S H4S 109.5 . . ?
S1S C2S H6S 109.5 . . ?
H5S C2S H4S 109.5 . . ?
H5S C2S H6S 109.5 . . ?
H4S C2S H6S 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C12 N3 0.4(6) . . . 3_666 ?
O3 C11 C7 N2 52.4(5) . . . . ?
N3 C11 C7 N2 -130.3(4) . . . . ?
N1 C1 C12 N3 179.4(4) . . . 3_666 ?
N1 C2 C6 O2 3.3(6) . . . . ?
N1 C2 C6 N2 -171.4(4) . . . . ?
C11 N3 C13 C14 79.7(5) . . . . ?
C1 N1 C2 C6 70.8(5) . . . . ?
C1 N1 C3 C4 107.9(4) . . . . ?
C2 N1 C1 O1 -174.9(4) . . . . ?
C2 N1 C1 C12 6.1(6) . . . . ?
C2 N1 C3 C4 -77.2(5) . . . . ?
C3 N1 C1 O1 -0.3(6) . . . . ?
C3 N1 C1 C12 -179.3(4) . . . . ?
C3 N1 C2 C6 -104.0(4) . . . . ?
C13 N3 C11 O3 4.9(6) . . . . ?
C13 N3 C11 C7 -172.4(4) . . . . ?
C6 N2 C7 C11 84.7(5) . . . . ?
C6 N2 C8 C9 88.9(5) . . . . ?
C7 N2 C6 O2 -16.5(6) . . . . ?
C7 N2 C6 C2 158.3(4) . . . . ?
C7 N2 C8 C9 -74.8(5) . . . . ?
C12 N3 C11 O3 -176.6(4) 3_666 . . . ?
C12 N3 C11 C7 6.1(6) 3_666 . . . ?
C12 N3 C13 C14 -99.0(5) 3_666 . . . ?
C8 N2 C6 O2 179.5(4) . . . . ?
C8 N2 C6 C2 -5.6(6) . . . . ?
C8 N2 C7 C11 -110.6(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_completion    2015-11-10
_olex2_date_sample_data_collection 2015-11-09
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_frozen
_database_code_depnum_ccdc_archive 'CCDC 1491788'
_audit_update_record             
;
2016-07-09 deposited with the CCDC.
2016-09-23 downloaded from the CCDC.
;
_audit_creation_date             2016-06-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H40 N8 O8, 2(C H4 O)'
_chemical_formula_sum            'C42 H48 N8 O10'
_chemical_formula_weight         824.88
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   29.138(11)
_cell_length_b                   8.033(2)
_cell_length_c                   21.635(8)
_cell_angle_alpha                90
_cell_angle_beta                 118.774(7)
_cell_angle_gamma                90
_cell_volume                     4439(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4400
_cell_measurement_theta_min      1.4308
_cell_measurement_theta_max      28.2484
_cell_measurement_temperature    100(2)
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3903
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1426
_diffrn_reflns_av_unetI/netI     0.1823
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17766
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.454
_diffrn_reflns_theta_min         1.595
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'AFC7S Rigaku'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2150
_reflns_number_total             5416
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2229
_refine_ls_R_factor_gt           0.0890
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0721P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1798
_refine_ls_wR_factor_ref         0.2361
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,
 H13B), C17(H17A,H17B), C18(H18A,H18B)
2.b Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC)
2.c Idealised tetrahedral OH refined as rotating group:
 O1S(H1S)
2.d :
 C5(H5), C10(H10), C15(H15), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.57228(10) 0.6075(3) 0.08657(15) 0.0438(7) Uani 1 1 d . . . . .
O2 O 0.70536(11) 0.4426(3) 0.26563(15) 0.0441(7) Uani 1 1 d . . . . .
O3 O 0.62191(10) 0.3802(3) 0.35698(14) 0.0403(7) Uani 1 1 d . . . . .
O4 O 0.52745(10) 0.6237(3) 0.35321(15) 0.0439(7) Uani 1 1 d . . . . .
N1 N 0.63240(12) 0.6841(3) 0.19697(16) 0.0365(8) Uani 1 1 d . . . . .
N2 N 0.71383(12) 0.4986(3) 0.37374(17) 0.0361(8) Uani 1 1 d . . . . .
N3 N 0.62492(12) 0.5187(3) 0.44977(16) 0.0365(8) Uani 1 1 d . . . . .
N4 N 0.48499(13) 0.4164(4) 0.37464(17) 0.0401(8) Uani 1 1 d . . . . .
C1 C 0.59002(15) 0.5965(4) 0.1510(2) 0.0353(9) Uani 1 1 d . . . . .
C2 C 0.65462(15) 0.6711(4) 0.2729(2) 0.0373(9) Uani 1 1 d . . . . .
H2A H 0.6260 0.6549 0.2847 0.045 Uiso 1 1 calc R . . . .
H2B H 0.6728 0.7764 0.2950 0.045 Uiso 1 1 calc R . . . .
C3 C 0.66307(16) 0.7771(4) 0.1708(2) 0.0425(10) Uani 1 1 d . . . . .
H3A H 0.6477 0.7592 0.1194 0.051 Uiso 1 1 calc R . . . .
H3B H 0.6993 0.7336 0.1937 0.051 Uiso 1 1 calc R . . . .
C4 C 0.66431(15) 0.9572(5) 0.1850(2) 0.0411(10) Uani 1 1 d . . . . .
C5 C 0.66794(17) 1.1010(5) 0.1964(2) 0.0489(11) Uani 1 1 d . . . . .
H5 H 0.6709 1.2172 0.2057 0.059 Uiso 1 1 calc R . . . .
C6 C 0.69360(14) 0.5257(4) 0.3034(2) 0.0380(10) Uani 1 1 d . . . . .
C7 C 0.69300(15) 0.5735(4) 0.4156(2) 0.0374(9) Uani 1 1 d . . . . .
H7A H 0.6847 0.6919 0.4021 0.045 Uiso 1 1 calc R . . . .
H7B H 0.7197 0.5692 0.4660 0.045 Uiso 1 1 calc R . . . .
C8 C 0.74600(16) 0.3482(4) 0.4036(2) 0.0438(10) Uani 1 1 d . . . . .
H8A H 0.7253 0.2634 0.4127 0.053 Uiso 1 1 calc R . . . .
H8B H 0.7556 0.3014 0.3691 0.053 Uiso 1 1 calc R . . . .
C9 C 0.79344(18) 0.3856(4) 0.4692(2) 0.0448(10) Uani 1 1 d . . . . .
C10 C 0.8306(2) 0.4180(5) 0.5228(3) 0.0581(13) Uani 1 1 d . . . . .
H10 H 0.8607 0.4442 0.5663 0.070 Uiso 1 1 calc R . . . .
C11 C 0.64340(15) 0.4826(4) 0.4048(2) 0.0356(9) Uani 1 1 d . . . . .
C12 C 0.58065(15) 0.4247(5) 0.4444(2) 0.0409(10) Uani 1 1 d . . . . .
H12A H 0.5810 0.4266 0.4904 0.049 Uiso 1 1 calc R . . . .
H12B H 0.5836 0.3074 0.4328 0.049 Uiso 1 1 calc R . . . .
C13 C 0.64606(16) 0.6536(4) 0.5017(2) 0.0437(10) Uani 1 1 d . . . . .
H13A H 0.6171 0.7033 0.5071 0.052 Uiso 1 1 calc R . . . .
H13B H 0.6602 0.7413 0.4834 0.052 Uiso 1 1 calc R . . . .
C14 C 0.68771(16) 0.6008(4) 0.5718(2) 0.0402(10) Uani 1 1 d . . . . .
C15 C 0.72046(18) 0.5617(5) 0.6283(2) 0.0498(11) Uani 1 1 d . . . . .
H15 H 0.7469 0.5300 0.6740 0.060 Uiso 1 1 calc R . . . .
C16 C 0.52841(16) 0.4985(5) 0.3869(2) 0.0390(9) Uani 1 1 d . . . . .
C17 C 0.56511(15) 0.4784(5) 0.1815(2) 0.0403(10) Uani 1 1 d . . . . .
H17A H 0.5890 0.3836 0.2048 0.048 Uiso 1 1 calc R . . . .
H17B H 0.5594 0.5375 0.2173 0.048 Uiso 1 1 calc R . . . .
C18 C 0.48334(16) 0.2862(4) 0.4218(2) 0.0438(10) Uani 1 1 d . . . . .
H18A H 0.5085 0.3159 0.4711 0.053 Uiso 1 1 calc R . . . .
H18B H 0.4479 0.2848 0.4174 0.053 Uiso 1 1 calc R . . . .
C19 C 0.49569(16) 0.1188(5) 0.4074(2) 0.0452(10) Uani 1 1 d . . . . .
C20 C 0.50485(19) -0.0187(6) 0.3980(3) 0.0597(13) Uani 1 1 d . . . . .
H20 H 0.5122 -0.1297 0.3903 0.072 Uiso 1 1 calc R . . . .
O1S O 0.40190(11) 0.8492(3) 0.15084(15) 0.0505(8) Uani 1 1 d . . . . .
H1S H 0.4247 0.7840 0.1515 0.076 Uiso 1 1 calc GR . . . .
C1S C 0.4258(2) 0.9614(5) 0.2092(3) 0.0668(14) Uani 1 1 d . . . . .
H1SA H 0.3985 1.0224 0.2139 0.100 Uiso 1 1 calc GR . . . .
H1SB H 0.4480 1.0404 0.2011 0.100 Uiso 1 1 calc GR . . . .
H1SC H 0.4472 0.8984 0.2525 0.100 Uiso 1 1 calc GR . . . .



_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.234(4) . ?
O2 C6 1.224(4) . ?
O3 C11 1.231(4) . ?
O4 C16 1.235(4) . ?
N1 C1 1.352(5) . ?
N1 C2 1.451(5) . ?
N1 C3 1.471(5) . ?
N2 C6 1.360(5) . ?
N2 C7 1.442(5) . ?
N2 C8 1.474(4) . ?
N3 C11 1.351(5) . ?
N3 C12 1.451(5) . ?
N3 C13 1.466(5) . ?
N4 C16 1.335(5) . ?
N4 C17 1.465(5) 2_655 ?
N4 C18 1.478(5) . ?
C1 C17 1.525(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C6 1.539(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.476(6) . ?
C4 C5 1.175(5) . ?
C5 H5 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C11 1.534(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.458(6) . ?
C9 C10 1.174(6) . ?
C10 H10 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C16 1.547(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.476(6) . ?
C14 C15 1.176(5) . ?
C15 H15 0.9500 . ?
C17 N4 1.465(5) 2_655 ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.464(5) . ?
C19 C20 1.178(5) . ?
C20 H20 0.9500 . ?
O1S H1S 0.8400 . ?
O1S C1S 1.430(5) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 123.2(3) . . ?
C1 N1 C3 119.3(3) . . ?
C2 N1 C3 116.7(3) . . ?
C6 N2 C7 123.3(3) . . ?
C6 N2 C8 117.6(3) . . ?
C7 N2 C8 116.0(3) . . ?
C11 N3 C12 118.6(3) . . ?
C11 N3 C13 123.0(3) . . ?
C12 N3 C13 118.4(3) . . ?
C16 N4 C17 117.9(3) . 2_655 ?
C16 N4 C18 123.7(3) . . ?
C17 N4 C18 117.5(3) 2_655 . ?
O1 C1 N1 122.1(3) . . ?
O1 C1 C17 120.3(3) . . ?
N1 C1 C17 117.5(3) . . ?
N1 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
N1 C2 C6 112.0(3) . . ?
H2A C2 H2B 107.9 . . ?
C6 C2 H2A 109.2 . . ?
C6 C2 H2B 109.2 . . ?
N1 C3 H3A 109.2 . . ?
N1 C3 H3B 109.2 . . ?
N1 C3 C4 112.2(3) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C5 C4 C3 176.3(4) . . ?
C4 C5 H5 180.0 . . ?
O2 C6 N2 123.3(4) . . ?
O2 C6 C2 121.0(4) . . ?
N2 C6 C2 115.7(3) . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 C11 110.9(3) . . ?
H7A C7 H7B 108.1 . . ?
C11 C7 H7A 109.5 . . ?
C11 C7 H7B 109.5 . . ?
N2 C8 H8A 109.4 . . ?
N2 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 N2 111.3(3) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C10 C9 C8 177.7(5) . . ?
C9 C10 H10 180.0 . . ?
O3 C11 N3 122.1(3) . . ?
O3 C11 C7 120.5(3) . . ?
N3 C11 C7 117.5(3) . . ?
N3 C12 H12A 109.4 . . ?
N3 C12 H12B 109.4 . . ?
N3 C12 C16 111.0(3) . . ?
H12A C12 H12B 108.0 . . ?
C16 C12 H12A 109.4 . . ?
C16 C12 H12B 109.4 . . ?
N3 C13 H13A 108.7 . . ?
N3 C13 H13B 108.7 . . ?
N3 C13 C14 114.1(3) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C15 C14 C13 178.3(5) . . ?
C14 C15 H15 180.0 . . ?
O4 C16 N4 122.3(4) . . ?
O4 C16 C12 121.4(4) . . ?
N4 C16 C12 116.3(3) . . ?
N4 C17 C1 110.2(3) 2_655 . ?
N4 C17 H17A 109.6 2_655 . ?
N4 C17 H17B 109.6 2_655 . ?
C1 C17 H17A 109.6 . . ?
C1 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
N4 C18 H18A 108.7 . . ?
N4 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 N4 114.2(3) . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C20 C19 C18 176.8(5) . . ?
C19 C20 H20 180.0 . . ?
C1S O1S H1S 109.5 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C17 N4 -11.3(5) . . . 2_655 ?
N1 C1 C17 N4 170.2(3) . . . 2_655 ?
N1 C2 C6 O2 4.5(5) . . . . ?
N1 C2 C6 N2 -176.1(3) . . . . ?
N2 C7 C11 O3 -11.3(5) . . . . ?
N2 C7 C11 N3 168.2(3) . . . . ?
N3 C12 C16 O4 -1.6(5) . . . . ?
N3 C12 C16 N4 176.5(3) . . . . ?
C1 N1 C2 C6 85.5(4) . . . . ?
C1 N1 C3 C4 119.8(4) . . . . ?
C2 N1 C1 O1 -178.8(3) . . . . ?
C2 N1 C1 C17 -0.3(5) . . . . ?
C2 N1 C3 C4 -69.7(4) . . . . ?
C3 N1 C1 O1 -8.9(5) . . . . ?
C3 N1 C1 C17 169.6(3) . . . . ?
C3 N1 C2 C6 -84.6(4) . . . . ?
C6 N2 C7 C11 78.3(4) . . . . ?
C6 N2 C8 C9 135.1(4) . . . . ?
C7 N2 C6 O2 -167.6(3) . . . . ?
C7 N2 C6 C2 13.0(5) . . . . ?
C7 N2 C8 C9 -64.0(4) . . . . ?
C8 N2 C6 O2 -8.2(5) . . . . ?
C8 N2 C6 C2 172.4(3) . . . . ?
C8 N2 C7 C11 -81.4(4) . . . . ?
C11 N3 C12 C16 -83.8(4) . . . . ?
C11 N3 C13 C14 -92.9(4) . . . . ?
C12 N3 C11 O3 4.6(5) . . . . ?
C12 N3 C11 C7 -175.0(3) . . . . ?
C12 N3 C13 C14 89.9(4) . . . . ?
C13 N3 C11 O3 -172.6(3) . . . . ?
C13 N3 C11 C7 7.8(5) . . . . ?
C13 N3 C12 C16 93.5(4) . . . . ?
C16 N4 C18 C19 -87.2(4) . . . . ?
C17 N4 C16 O4 0.5(5) 2_655 . . . ?
C17 N4 C16 C12 -177.5(3) 2_655 . . . ?
C17 N4 C18 C19 104.0(4) 2_655 . . . ?
C18 N4 C16 O4 -168.3(3) . . . . ?
C18 N4 C16 C12 13.7(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'Mitegen microloop'
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_ale60_b2_1bis
_database_code_depnum_ccdc_archive 'CCDC 1491789'
_audit_update_record             
;
2016-07-09 deposited with the CCDC.
2016-09-23 downloaded from the CCDC.
;
_audit_creation_date             2016-06-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H40 N8 O8, (C H4 O),2 (H2 O)'
_chemical_formula_sum            'C41 H48 N8 O11'
_chemical_formula_weight         828.87
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   29.227(11)
_cell_length_b                   7.997(3)
_cell_length_c                   21.680(8)
_cell_angle_alpha                90
_cell_angle_beta                 119.615(7)
_cell_angle_gamma                90
_cell_volume                     4405(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16615
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      28.598
_cell_measurement_theta_min      1.603
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1752
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16615
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.598
_diffrn_reflns_theta_min         1.603
_diffrn_ambient_temperature      100.0(5)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_detector_type            'Rigaku Mercury2'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device       AFC7S
_diffrn_measurement_device_type  Rigaku_AFC7_Mo
_diffrn_measurement_method       dtprofit.ref
_diffrn_measurement_specimen_support 'Mitegen 150um'
_diffrn_radiation_collimation    0.5
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_target            Mo
_diffrn_source_type              'Sealed Tube'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3060
_reflns_number_total             5330
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         5330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.0967
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1007P)²+6.7458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2380
_refine_ls_wR_factor_ref         0.2725
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: C1S(0.5) H1SA(0.5) H1SB(0.5) H1SC(0.5) O2S(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,
 H13B), C17(H17A,H17B), C18(H18A,H18B)
3.b Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC)
3.c Idealised tetrahedral OH refined as rotating group:
 O1S(H1S)
3.d :
 C5(H5), C10(H10), C15(H15), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.57361(11) 0.5942(4) 0.08397(14) 0.0649(7) Uani 1 1 d . . . . .
O2 O 0.70670(11) 0.4491(3) 0.26860(15) 0.0622(7) Uani 1 1 d . . . . .
O3 O 0.62257(9) 0.3740(3) 0.35448(12) 0.0473(6) Uani 1 1 d . . . . .
O4 O 0.52431(11) 0.6042(4) 0.35238(14) 0.0648(7) Uani 1 1 d . . . . .
N1 N 0.63160(12) 0.6828(4) 0.19497(15) 0.0533(7) Uani 1 1 d . . . . .
N2 N 0.71386(11) 0.5090(4) 0.37590(16) 0.0497(7) Uani 1 1 d . . . . .
N3 N 0.62324(11) 0.5024(4) 0.44771(15) 0.0474(7) Uani 1 1 d . . . . .
N4 N 0.48293(12) 0.3992(4) 0.37665(16) 0.0575(8) Uani 1 1 d . . . . .
C1 C 0.59109(14) 0.5881(5) 0.1486(2) 0.0554(9) Uani 1 1 d . . . . .
C2 C 0.65344(14) 0.6738(5) 0.27147(19) 0.0536(9) Uani 1 1 d . . . . .
H2A H 0.6245 0.6569 0.2821 0.064 Uiso 1 1 calc R . . . .
H2B H 0.6708 0.7812 0.2930 0.064 Uiso 1 1 calc R . . . .
C3 C 0.66203(17) 0.7804(5) 0.1698(2) 0.0614(10) Uani 1 1 d . . . . .
H3A H 0.6986 0.7375 0.1931 0.074 Uiso 1 1 calc R . . . .
H3B H 0.6465 0.7632 0.1181 0.074 Uiso 1 1 calc R . . . .
C4 C 0.66334(14) 0.9584(5) 0.1838(2) 0.0575(9) Uani 1 1 d . . . . .
C5 C 0.66870(16) 1.1044(6) 0.1969(2) 0.0649(10) Uani 1 1 d . . . . .
H5 H 0.6730 1.2206 0.2072 0.078 Uiso 1 1 calc R . . . .
C6 C 0.69329(14) 0.5319(5) 0.3048(2) 0.0516(8) Uani 1 1 d . . . . .
C7 C 0.69062(13) 0.5794(4) 0.41568(19) 0.0484(8) Uani 1 1 d . . . . .
H7A H 0.6800 0.6966 0.4006 0.058 Uiso 1 1 calc R . . . .
H7B H 0.7169 0.5797 0.4669 0.058 Uiso 1 1 calc R . . . .
C8 C 0.74797(16) 0.3617(5) 0.4074(2) 0.0607(10) Uani 1 1 d . . . . .
H8A H 0.7275 0.2712 0.4137 0.073 Uiso 1 1 calc R . . . .
H8B H 0.7601 0.3207 0.3748 0.073 Uiso 1 1 calc R . . . .
C9 C 0.79346(16) 0.4023(5) 0.4758(2) 0.0626(10) Uani 1 1 d . . . . .
C10 C 0.82968(18) 0.4390(5) 0.5314(3) 0.0762(13) Uani 1 1 d . . . . .
H10 H 0.8588 0.4685 0.5760 0.091 Uiso 1 1 calc R . . . .
C11 C 0.64229(13) 0.4770(4) 0.40328(17) 0.0433(7) Uani 1 1 d . . . . .
C12 C 0.57953(14) 0.4012(5) 0.4404(2) 0.0558(9) Uani 1 1 d . . . . .
H12A H 0.5812 0.3919 0.4870 0.067 Uiso 1 1 calc R . . . .
H12B H 0.5823 0.2872 0.4247 0.067 Uiso 1 1 calc R . . . .
C13 C 0.64208(16) 0.6388(5) 0.50033(19) 0.0585(10) Uani 1 1 d . . . . .
H13A H 0.6539 0.7328 0.4819 0.070 Uiso 1 1 calc R . . . .
H13B H 0.6123 0.6793 0.5058 0.070 Uiso 1 1 calc R . . . .
C14 C 0.68544(16) 0.5912(5) 0.5705(2) 0.0531(8) Uani 1 1 d . . . . .
C15 C 0.71975(17) 0.5563(5) 0.6276(2) 0.0640(10) Uani 1 1 d . . . . .
H15 H 0.7474 0.5281 0.6737 0.077 Uiso 1 1 calc R . . . .
C16 C 0.52694(15) 0.4783(5) 0.38664(19) 0.0560(9) Uani 1 1 d . . . . .
C17 C 0.56782(15) 0.4628(6) 0.1794(2) 0.0660(11) Uani 1 1 d . . . . .
H17A H 0.5926 0.3684 0.2017 0.079 Uiso 1 1 calc R . . . .
H17B H 0.5629 0.5183 0.2166 0.079 Uiso 1 1 calc R . . . .
C18 C 0.48255(16) 0.2684(5) 0.4240(2) 0.0617(10) Uani 1 1 d . . . . .
H18A H 0.4479 0.2695 0.4218 0.074 Uiso 1 1 calc R . . . .
H18B H 0.5096 0.2957 0.4733 0.074 Uiso 1 1 calc R . . . .
C19 C 0.49257(16) 0.0985(6) 0.4073(2) 0.0662(11) Uani 1 1 d . . . . .
C20 C 0.5005(2) -0.0379(7) 0.3947(3) 0.0939(17) Uani 1 1 d . . . . .
H20 H 0.5069 -0.1482 0.3846 0.113 Uiso 1 1 calc R . . . .
O1S O 0.40909(14) -0.1653(4) 0.15917(18) 0.0826(10) Uani 1 1 d . . . A 2
H1S H 0.4340 -0.2300 0.1668 0.124 Uiso 1 1 calc GR . . A 2
C1S C 0.4266(5) -0.0454(17) 0.2121(6) 0.112(4) Uani 0.5 1 d . . P A 2
H1SA H 0.3963 0.0140 0.2094 0.168 Uiso 0.5 1 calc GR . P A 2
H1SB H 0.4494 0.0343 0.2058 0.168 Uiso 0.5 1 calc GR . P A 2
H1SC H 0.4464 -0.0997 0.2585 0.168 Uiso 0.5 1 calc GR . P A 2
O2S O 0.4497(3) 0.1333(9) 0.2259(4) 0.0877(19) Uiso 0.5 1 d . . P B 3


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.233(4) . ?
O2 C6 1.229(4) . ?
O3 C11 1.236(4) . ?
O4 C16 1.231(5) . ?
N1 C1 1.345(5) . ?
N1 C2 1.455(5) . ?
N1 C3 1.476(4) . ?
N2 C6 1.363(5) . ?
N2 C7 1.450(4) . ?
N2 C8 1.474(5) . ?
N3 C11 1.345(4) . ?
N3 C12 1.453(5) . ?
N3 C13 1.474(5) . ?
N4 C16 1.351(5) . ?
N4 C17 1.468(5) 2_655 ?
N4 C18 1.470(5) . ?
C1 C17 1.537(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C6 1.527(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.452(6) . ?
C4 C5 1.194(6) . ?
C5 H5 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C11 1.537(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.457(6) . ?
C9 C10 1.182(6) . ?
C10 H10 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C16 1.527(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.470(5) . ?
C14 C15 1.179(5) . ?
C15 H15 0.9500 . ?
C17 N4 1.468(5) 2_655 ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.472(6) . ?
C19 C20 1.175(6) . ?
C20 H20 0.9500 . ?
O1S H1S 0.8400 . ?
O1S C1S 1.385(11) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 123.5(3) . . ?
C1 N1 C3 119.4(3) . . ?
C2 N1 C3 116.3(3) . . ?
C6 N2 C7 123.1(3) . . ?
C6 N2 C8 116.8(3) . . ?
C7 N2 C8 116.3(3) . . ?
C11 N3 C12 119.4(3) . . ?
C11 N3 C13 122.5(3) . . ?
C12 N3 C13 117.9(3) . . ?
C16 N4 C17 117.6(4) . 2_655 ?
C16 N4 C18 123.8(3) . . ?
C17 N4 C18 118.2(3) 2_655 . ?
O1 C1 N1 123.0(3) . . ?
O1 C1 C17 119.8(3) . . ?
N1 C1 C17 117.2(3) . . ?
N1 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
N1 C2 C6 112.2(3) . . ?
H2A C2 H2B 107.9 . . ?
C6 C2 H2A 109.2 . . ?
C6 C2 H2B 109.2 . . ?
N1 C3 H3A 108.9 . . ?
N1 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 N1 113.5(3) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C5 C4 C3 174.6(4) . . ?
C4 C5 H5 180.0 . . ?
O2 C6 N2 123.2(3) . . ?
O2 C6 C2 120.5(3) . . ?
N2 C6 C2 116.2(3) . . ?
N2 C7 H7A 109.6 . . ?
N2 C7 H7B 109.6 . . ?
N2 C7 C11 110.4(3) . . ?
H7A C7 H7B 108.1 . . ?
C11 C7 H7A 109.6 . . ?
C11 C7 H7B 109.6 . . ?
N2 C8 H8A 109.4 . . ?
N2 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 N2 111.2(3) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C10 C9 C8 178.2(5) . . ?
C9 C10 H10 180.0 . . ?
O3 C11 N3 122.1(3) . . ?
O3 C11 C7 120.3(3) . . ?
N3 C11 C7 117.6(3) . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
N3 C12 C16 110.9(3) . . ?
H12A C12 H12B 108.0 . . ?
C16 C12 H12A 109.5 . . ?
C16 C12 H12B 109.5 . . ?
N3 C13 H13A 108.7 . . ?
N3 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 N3 114.3(3) . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C15 C14 C13 178.2(4) . . ?
C14 C15 H15 180.0 . . ?
O4 C16 N4 121.0(3) . . ?
O4 C16 C12 122.0(4) . . ?
N4 C16 C12 116.9(3) . . ?
N4 C17 C1 110.4(3) 2_655 . ?
N4 C17 H17A 109.6 2_655 . ?
N4 C17 H17B 109.6 2_655 . ?
C1 C17 H17A 109.6 . . ?
C1 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
N4 C18 H18A 108.7 . . ?
N4 C18 H18B 108.7 . . ?
N4 C18 C19 114.4(3) . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C20 C19 C18 179.1(5) . . ?
C19 C20 H20 180.0 . . ?
C1S O1S H1S 109.5 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C17 N4 -15.9(6) . . . 2_655 ?
N1 C1 C17 N4 166.5(3) . . . 2_655 ?
N1 C2 C6 O2 5.6(5) . . . . ?
N1 C2 C6 N2 -176.9(3) . . . . ?
N2 C7 C11 O3 -13.5(4) . . . . ?
N2 C7 C11 N3 165.7(3) . . . . ?
N3 C12 C16 O4 4.1(5) . . . . ?
N3 C12 C16 N4 -177.8(3) . . . . ?
C1 N1 C2 C6 83.3(4) . . . . ?
C1 N1 C3 C4 123.0(4) . . . . ?
C2 N1 C1 O1 -178.4(3) . . . . ?
C2 N1 C1 C17 -0.9(5) . . . . ?
C2 N1 C3 C4 -67.2(5) . . . . ?
C3 N1 C1 O1 -9.4(6) . . . . ?
C3 N1 C1 C17 168.1(4) . . . . ?
C3 N1 C2 C6 -86.0(4) . . . . ?
C6 N2 C7 C11 77.5(4) . . . . ?
C6 N2 C8 C9 139.1(3) . . . . ?
C7 N2 C6 O2 -166.2(3) . . . . ?
C7 N2 C6 C2 16.3(5) . . . . ?
C7 N2 C8 C9 -62.0(4) . . . . ?
C8 N2 C6 O2 -8.9(5) . . . . ?
C8 N2 C6 C2 173.7(3) . . . . ?
C8 N2 C7 C11 -80.0(4) . . . . ?
C11 N3 C12 C16 -86.9(4) . . . . ?
C11 N3 C13 C14 -92.3(4) . . . . ?
C12 N3 C11 O3 2.7(5) . . . . ?
C12 N3 C11 C7 -176.4(3) . . . . ?
C12 N3 C13 C14 92.7(4) . . . . ?
C13 N3 C11 O3 -172.2(3) . . . . ?
C13 N3 C11 C7 8.7(4) . . . . ?
C13 N3 C12 C16 88.2(4) . . . . ?
C16 N4 C18 C19 -86.4(5) . . . . ?
C17 N4 C16 O4 3.7(5) 2_655 . . . ?
C17 N4 C16 C12 -174.5(3) 2_655 . . . ?
C17 N4 C18 C19 101.7(4) 2_655 . . . ?
C18 N4 C16 O4 -168.3(3) . . . . ?
C18 N4 C16 C12 13.5(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_wat_24h_ct
_database_code_depnum_ccdc_archive 'CCDC 1491790'
_audit_update_record             
;
2016-07-09 deposited with the CCDC.
2016-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H40 N8 O8, 4 (H2O)'
_chemical_formula_sum            'C40 H48 N8 O12'
_chemical_formula_weight         832.86

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   29.250(12)
_cell_length_b                   7.997(3)
_cell_length_c                   21.648(9)
_cell_angle_alpha                90
_cell_angle_beta                 120.242(9)
_cell_angle_gamma                90
_cell_volume                     4375(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3457
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3720
_cell_measurement_theta_min      1.6117

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             1760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6703
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Rigaku AFC7S'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 13.6612
_diffrn_reflns_number            17219
_diffrn_reflns_av_unetI/netI     0.1668
_diffrn_reflns_av_R_equivalents  0.1169
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.612
_diffrn_reflns_theta_max         28.516
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             5150
_reflns_number_gt                1763
_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_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR 2014 (Burla, 2015)'
_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)+(0.1715P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5150
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2658
_refine_ls_R_factor_gt           0.1178
_refine_ls_wR_factor_ref         0.3762
_refine_ls_wR_factor_gt          0.2771
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_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
O1 O 0.57470(17) 0.5858(5) 0.0818(2) 0.0571(12) Uani 1 1 d . . . . .
O2 O 0.70690(17) 0.4468(5) 0.2696(2) 0.0530(11) Uani 1 1 d . . . . .
O3 O 0.62222(15) 0.3722(5) 0.35237(19) 0.0460(10) Uani 1 1 d . . . . .
O4 O 0.52226(15) 0.5952(6) 0.3513(2) 0.0545(11) Uani 1 1 d . . . . .
N1 N 0.6317(2) 0.6803(6) 0.1934(2) 0.0508(13) Uani 1 1 d . . . . .
N2 N 0.71347(18) 0.5082(6) 0.3764(2) 0.0424(12) Uani 1 1 d . . . . .
N3 N 0.62271(18) 0.4963(6) 0.4466(2) 0.0433(12) Uani 1 1 d . . . . .
N4 N 0.48208(19) 0.3919(6) 0.3778(2) 0.0456(12) Uani 1 1 d . . . . .
C1 C 0.5917(3) 0.5814(7) 0.1468(3) 0.0471(15) Uani 1 1 d . . . . .
C2 C 0.6534(2) 0.6736(7) 0.2701(3) 0.0434(14) Uani 1 1 d . . . . .
H2A H 0.6242 0.6584 0.2802 0.052 Uiso 1 1 calc R U . . .
H2B H 0.6710 0.7812 0.2915 0.052 Uiso 1 1 calc R U . . .
C3 C 0.6617(3) 0.7769(7) 0.1682(3) 0.0520(16) Uani 1 1 d . . . . .
H3A H 0.6984 0.7334 0.1913 0.062 Uiso 1 1 calc R U . . .
H3B H 0.6455 0.7609 0.1159 0.062 Uiso 1 1 calc R U . . .
C4 C 0.6633(2) 0.9550(9) 0.1833(3) 0.0495(16) Uani 1 1 d . . . . .
C5 C 0.6689(3) 1.1004(10) 0.1958(4) 0.0612(18) Uani 1 1 d . . . . .
H5 H 0.6735 1.2168 0.2059 0.073 Uiso 1 1 calc R U . . .
C6 C 0.6928(2) 0.5333(7) 0.3047(3) 0.0443(14) Uani 1 1 d . . . . .
C7 C 0.6894(2) 0.5805(7) 0.4151(3) 0.0413(13) Uani 1 1 d . . . . .
H7A H 0.6779 0.6965 0.3987 0.050 Uiso 1 1 calc R U . . .
H7B H 0.7156 0.5835 0.4669 0.050 Uiso 1 1 calc R U . . .
C8 C 0.7484(3) 0.3633(8) 0.4093(3) 0.0515(16) Uani 1 1 d . . . . .
H8A H 0.7609 0.3222 0.3772 0.062 Uiso 1 1 calc R U . . .
H8B H 0.7283 0.2721 0.4158 0.062 Uiso 1 1 calc R U . . .
C9 C 0.7942(3) 0.4079(8) 0.4790(4) 0.0516(16) Uani 1 1 d . . . . .
C10 C 0.8303(3) 0.4477(8) 0.5347(4) 0.0636(19) Uani 1 1 d . . . . .
H10 H 0.8594 0.4797 0.5796 0.076 Uiso 1 1 calc R U . . .
C11 C 0.6419(2) 0.4755(7) 0.4019(3) 0.0431(14) Uani 1 1 d . . . . .
C12 C 0.5794(2) 0.3947(9) 0.4390(3) 0.0522(17) Uani 1 1 d . . . . .
H12A H 0.5822 0.3827 0.4863 0.063 Uiso 1 1 calc R U . . .
H12B H 0.5822 0.2817 0.4225 0.063 Uiso 1 1 calc R U . . .
C13 C 0.6404(2) 0.6318(8) 0.4995(3) 0.0497(16) Uani 1 1 d . . . . .
H13A H 0.6104 0.6667 0.5054 0.060 Uiso 1 1 calc R U . . .
H13B H 0.6507 0.7290 0.4809 0.060 Uiso 1 1 calc R U . . .
C14 C 0.6853(3) 0.5861(7) 0.5701(3) 0.0482(15) Uani 1 1 d . . . . .
C15 C 0.7201(3) 0.5531(8) 0.6265(4) 0.0639(19) Uani 1 1 d . . . . .
H15 H 0.7486 0.5260 0.6727 0.077 Uiso 1 1 calc R U . . .
C16 C 0.5259(3) 0.4682(9) 0.3867(3) 0.0533(16) Uani 1 1 d . . . . .
C17 C 0.5692(2) 0.4543(8) 0.1774(3) 0.0489(15) Uani 1 1 d . . . . .
H17A H 0.5941 0.3595 0.1987 0.059 Uiso 1 1 calc R U . . .
H17B H 0.5653 0.5077 0.2158 0.059 Uiso 1 1 calc R U . . .
C18 C 0.4831(2) 0.2594(8) 0.4260(3) 0.0528(16) Uani 1 1 d . . . . .
H18A H 0.5116 0.2846 0.4753 0.063 Uiso 1 1 calc R U . . .
H18B H 0.4491 0.2605 0.4254 0.063 Uiso 1 1 calc R U . . .
C19 C 0.4918(3) 0.0913(10) 0.4065(4) 0.0622(18) Uani 1 1 d . . . . .
C20 C 0.4979(3) -0.0463(11) 0.3921(4) 0.078(2) Uani 1 1 d . . . . .
H20 H 0.5028 -0.1569 0.3806 0.093 Uiso 1 1 calc R U . . .
O2SB O 0.4554(6) 0.1355(12) 0.2252(5) 0.055(5) Uiso 0.49(4) 1 d . . P A 1
O2SA O 0.4380(7) 0.1203(14) 0.2348(6) 0.071(5) Uiso 0.51(4) 1 d . . P A 2
O1S O 0.41260(19) -0.1799(6) 0.1648(2) 0.0692(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
O1 C1 1.236(7) . ?
O2 C6 1.242(6) . ?
O3 C11 1.242(6) . ?
O4 C16 1.245(7) . ?
N1 C1 1.350(8) . ?
N1 C2 1.450(7) . ?
N1 C3 1.467(7) . ?
N2 C6 1.366(7) . ?
N2 C7 1.459(7) . ?
N2 C8 1.470(7) . ?
N3 C11 1.350(7) . ?
N3 C12 1.444(8) . ?
N3 C13 1.469(7) . ?
N4 C16 1.342(8) . ?
N4 C17 1.456(7) 2_655 ?
N4 C18 1.477(7) . ?
C1 C17 1.531(8) . ?
C2 C6 1.509(8) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.457(9) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.187(9) . ?
C5 H5 0.9500 . ?
C7 C11 1.522(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.470(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.177(9) . ?
C10 H10 0.9500 . ?
C12 C16 1.514(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.473(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.160(9) . ?
C15 H15 0.9500 . ?
C17 N4 1.456(7) 2_655 ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.468(10) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.181(9) . ?
C20 H20 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
C1 N1 C2 123.3(5) . . ?
C1 N1 C3 119.1(4) . . ?
C2 N1 C3 116.6(5) . . ?
C6 N2 C7 121.9(5) . . ?
C6 N2 C8 118.0(4) . . ?
C7 N2 C8 116.9(4) . . ?
C11 N3 C12 120.5(5) . . ?
C11 N3 C13 122.6(5) . . ?
C12 N3 C13 116.6(4) . . ?
C16 N4 C17 118.4(5) . 2_655 ?
C16 N4 C18 123.1(5) . . ?
C17 N4 C18 118.2(5) 2_655 . ?
O1 C1 N1 122.3(5) . . ?
O1 C1 C17 119.9(6) . . ?
N1 C1 C17 117.8(5) . . ?
N1 C2 C6 112.4(5) . . ?
N1 C2 H2A 109.1 . . ?
C6 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C6 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 N1 112.9(5) . . ?
C4 C3 H3A 109.0 . . ?
N1 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
N1 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 174.0(7) . . ?
C4 C5 H5 180.0 . . ?
O2 C6 N2 121.3(5) . . ?
O2 C6 C2 121.1(5) . . ?
N2 C6 C2 117.6(5) . . ?
N2 C7 C11 109.5(4) . . ?
N2 C7 H7A 109.8 . . ?
C11 C7 H7A 109.8 . . ?
N2 C7 H7B 109.8 . . ?
C11 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
N2 C8 C9 111.0(5) . . ?
N2 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N2 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 178.2(7) . . ?
C9 C10 H10 180.0 . . ?
O3 C11 N3 121.5(5) . . ?
O3 C11 C7 120.7(5) . . ?
N3 C11 C7 117.8(5) . . ?
N3 C12 C16 112.6(5) . . ?
N3 C12 H12A 109.1 . . ?
C16 C12 H12A 109.1 . . ?
N3 C12 H12B 109.1 . . ?
C16 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
N3 C13 C14 113.9(5) . . ?
N3 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
N3 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 178.1(7) . . ?
C14 C15 H15 180.0 . . ?
O4 C16 N4 120.2(6) . . ?
O4 C16 C12 120.8(6) . . ?
N4 C16 C12 118.9(6) . . ?
N4 C17 C1 111.2(4) 2_655 . ?
N4 C17 H17A 109.4 2_655 . ?
C1 C17 H17A 109.4 . . ?
N4 C17 H17B 109.4 2_655 . ?
C1 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 N4 113.5(5) . . ?
C19 C18 H18A 108.9 . . ?
N4 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
N4 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C18 177.6(7) . . ?
C19 C20 H20 180.0 . . ?

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
C2 N1 C1 O1 -177.9(5) . . . . ?
C3 N1 C1 O1 -10.0(9) . . . . ?
C2 N1 C1 C17 -1.1(8) . . . . ?
C3 N1 C1 C17 166.9(5) . . . . ?
C1 N1 C2 C6 81.4(7) . . . . ?
C3 N1 C2 C6 -86.9(6) . . . . ?
C1 N1 C3 C4 125.6(6) . . . . ?
C2 N1 C3 C4 -65.6(7) . . . . ?
C7 N2 C6 O2 -165.8(5) . . . . ?
C8 N2 C6 O2 -7.0(8) . . . . ?
C7 N2 C6 C2 16.1(7) . . . . ?
C8 N2 C6 C2 175.0(5) . . . . ?
N1 C2 C6 O2 5.8(8) . . . . ?
N1 C2 C6 N2 -176.1(5) . . . . ?
C6 N2 C7 C11 79.3(6) . . . . ?
C8 N2 C7 C11 -79.8(6) . . . . ?
C6 N2 C8 C9 138.2(5) . . . . ?
C7 N2 C8 C9 -61.8(6) . . . . ?
C12 N3 C11 O3 1.8(8) . . . . ?
C13 N3 C11 O3 -171.8(5) . . . . ?
C12 N3 C11 C7 -177.0(5) . . . . ?
C13 N3 C11 C7 9.5(8) . . . . ?
N2 C7 C11 O3 -15.2(7) . . . . ?
N2 C7 C11 N3 163.6(5) . . . . ?
C11 N3 C12 C16 -87.4(6) . . . . ?
C13 N3 C12 C16 86.6(6) . . . . ?
C11 N3 C13 C14 -91.4(6) . . . . ?
C12 N3 C13 C14 94.8(6) . . . . ?
C17 N4 C16 O4 4.2(8) 2_655 . . . ?
C18 N4 C16 O4 -169.2(5) . . . . ?
C17 N4 C16 C12 -174.3(5) 2_655 . . . ?
C18 N4 C16 C12 12.3(8) . . . . ?
N3 C12 C16 O4 5.6(8) . . . . ?
N3 C12 C16 N4 -176.0(5) . . . . ?
O1 C1 C17 N4 -19.3(8) . . . 2_655 ?
N1 C1 C17 N4 163.7(5) . . . 2_655 ?
C16 N4 C18 C19 -86.2(7) . . . . ?
C17 N4 C18 C19 100.3(6) 2_655 . . . ?

_refine_diff_density_max         0.562
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.081


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_wat_met
_database_code_depnum_ccdc_archive 'CCDC 1491791'
_audit_update_record             
;
2016-07-28 deposited with the CCDC.
2016-09-23 downloaded from the CCDC.
;
_audit_creation_date             2016-06-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H40 N8 O8, 1.56(C H4 O), 0.88(H2 O)'
_chemical_formula_sum            'C41.56 H48 N8 O10.44'
_chemical_formula_weight         826.64
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   29.177(10)
_cell_length_b                   7.999(2)
_cell_length_c                   21.586(7)
_cell_angle_alpha                90
_cell_angle_beta                 119.075(7)
_cell_angle_gamma                90
_cell_volume                     4403(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4727
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_min      1.5970
_cell_measurement_theta_max      28.4967
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5710
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1748
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_av_unetI/netI     0.1248
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17194
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.700
_diffrn_reflns_theta_min         1.597
_diffrn_ambient_temperature      100.0(5)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_device_type  'Rigaku AFc7S'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2353
_reflns_number_total             5080
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR 2014 (Burla, 2015)'
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         5080
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2146
_refine_ls_R_factor_gt           0.1105
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1408P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2591
_refine_ls_wR_factor_ref         0.3272
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(O2S)=1-FVAR(1)
 Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(H1SC)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,
 H13B), C17(H17A,H17B), C18(H18A,H18B)
3.b Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC)
3.c Idealised tetrahedral OH refined as rotating group:
 O1S(H1S)
3.d :
 C5(H5), C10(H10), C15(H15), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.57256(13) 0.6005(4) 0.08512(16) 0.0504(9) Uani 1 1 d . . . . .
O2 O 0.70608(13) 0.4456(4) 0.26683(17) 0.0503(9) Uani 1 1 d . . . . .
O3 O 0.62218(12) 0.3770(4) 0.35570(16) 0.0429(8) Uani 1 1 d . . . . .
O4 O 0.52632(13) 0.6166(5) 0.35225(17) 0.0515(9) Uani 1 1 d . . . . .
N1 N 0.63213(15) 0.6821(5) 0.19612(19) 0.0405(9) Uani 1 1 d . . . . .
N2 N 0.71386(15) 0.5023(5) 0.3743(2) 0.0398(9) Uani 1 1 d . . . . .
N3 N 0.62397(15) 0.5111(5) 0.44870(19) 0.0413(10) Uani 1 1 d . . . . .
N4 N 0.48411(16) 0.4101(5) 0.37490(19) 0.0472(11) Uani 1 1 d . . . . .
C1 C 0.59036(19) 0.5946(6) 0.1500(2) 0.0437(12) Uani 1 1 d . . . . .
C2 C 0.65384(19) 0.6726(6) 0.2722(2) 0.0421(11) Uani 1 1 d . . . . .
H2A H 0.6251 0.6563 0.2836 0.051 Uiso 1 1 calc R . . . .
H2B H 0.6717 0.7791 0.2939 0.051 Uiso 1 1 calc R . . . .
C3 C 0.6625(2) 0.7794(6) 0.1703(3) 0.0506(13) Uani 1 1 d . . . . .
H3A H 0.6990 0.7373 0.1938 0.061 Uiso 1 1 calc R . . . .
H3B H 0.6474 0.7604 0.1187 0.061 Uiso 1 1 calc R . . . .
C4 C 0.66341(18) 0.9580(7) 0.1832(2) 0.0445(12) Uani 1 1 d . . . . .
C5 C 0.6681(2) 1.1015(8) 0.1967(3) 0.0564(14) Uani 1 1 d . . . . .
H5 H 0.6719 1.2174 0.2077 0.068 Uiso 1 1 calc R . . . .
C6 C 0.69317(17) 0.5276(6) 0.3036(2) 0.0397(11) Uani 1 1 d . . . . .
C7 C 0.69196(18) 0.5758(6) 0.4162(2) 0.0411(11) Uani 1 1 d . . . . .
H7A H 0.6829 0.6944 0.4027 0.049 Uiso 1 1 calc R . . . .
H7B H 0.7183 0.5715 0.4672 0.049 Uiso 1 1 calc R . . . .
C8 C 0.7467(2) 0.3537(6) 0.4048(3) 0.0493(13) Uani 1 1 d . . . . .
H8A H 0.7259 0.2665 0.4127 0.059 Uiso 1 1 calc R . . . .
H8B H 0.7571 0.3089 0.3708 0.059 Uiso 1 1 calc R . . . .
C9 C 0.7933(2) 0.3901(6) 0.4714(3) 0.0507(13) Uani 1 1 d . . . . .
C10 C 0.8304(2) 0.4263(7) 0.5264(3) 0.0617(15) Uani 1 1 d . . . . .
H10 H 0.8600 0.4552 0.5703 0.074 Uiso 1 1 calc R . . . .
C11 C 0.64236(18) 0.4784(6) 0.4032(2) 0.0393(11) Uani 1 1 d . . . . .
C12 C 0.57946(18) 0.4155(7) 0.4419(2) 0.0461(12) Uani 1 1 d . . . . .
H12A H 0.5800 0.4130 0.4881 0.055 Uiso 1 1 calc R . . . .
H12B H 0.5821 0.2990 0.4284 0.055 Uiso 1 1 calc R . . . .
C13 C 0.6438(2) 0.6454(7) 0.5008(2) 0.0506(13) Uani 1 1 d . . . . .
H13A H 0.6144 0.6894 0.5067 0.061 Uiso 1 1 calc R . . . .
H13B H 0.6562 0.7373 0.4820 0.061 Uiso 1 1 calc R . . . .
C14 C 0.6865(2) 0.5974(6) 0.5704(3) 0.0455(12) Uani 1 1 d . . . . .
C15 C 0.7201(2) 0.5589(7) 0.6275(3) 0.0521(13) Uani 1 1 d . . . . .
H15 H 0.7472 0.5279 0.6733 0.062 Uiso 1 1 calc R . . . .
C16 C 0.52805(18) 0.4921(7) 0.3860(2) 0.0458(13) Uani 1 1 d . . . . .
C17 C 0.5661(2) 0.4711(7) 0.1804(2) 0.0506(13) Uani 1 1 d . . . . .
H17A H 0.5903 0.3756 0.2024 0.061 Uiso 1 1 calc R . . . .
H17B H 0.5612 0.5272 0.2177 0.061 Uiso 1 1 calc R . . . .
C18 C 0.48300(19) 0.2797(7) 0.4221(2) 0.0503(13) Uani 1 1 d . . . . .
H18A H 0.5088 0.3088 0.4716 0.060 Uiso 1 1 calc R . . . .
H18B H 0.4479 0.2792 0.4185 0.060 Uiso 1 1 calc R . . . .
C19 C 0.4945(2) 0.1113(8) 0.4071(3) 0.0539(14) Uani 1 1 d . . . . .
C20 C 0.5031(3) -0.0291(9) 0.3980(4) 0.0753(19) Uani 1 1 d . . . . .
H20 H 0.5100 -0.1413 0.3907 0.090 Uiso 1 1 calc R . . . .
O1S O 0.40466(15) -0.1558(5) 0.15380(19) 0.0590(10) Uani 1 1 d . . . A 1
H1S H 0.4262 -0.2321 0.1599 0.089 Uiso 1 1 calc GR . . A 1
C1S C 0.4273(3) -0.0425(10) 0.2115(4) 0.065(3) Uani 0.782(13) 1 d . . P A 1
H1SA H 0.4483 -0.1046 0.2555 0.098 Uiso 0.782(13) 1 calc GR . P A 1
H1SB H 0.3994 0.0186 0.2147 0.098 Uiso 0.782(13) 1 calc GR . P A 1
H1SC H 0.4497 0.0368 0.2040 0.098 Uiso 0.782(13) 1 calc GR . P A 1
O2S O 0.4505(10) 0.134(3) 0.2238(13) 0.105(10) Uiso 0.218(13) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.237(5) . ?
O2 C6 1.222(5) . ?
O3 C11 1.212(5) . ?
O4 C16 1.221(6) . ?
N1 C1 1.337(6) . ?
N1 C2 1.446(5) . ?
N1 C3 1.477(5) . ?
N2 C6 1.356(6) . ?
N2 C7 1.461(5) . ?
N2 C8 1.467(6) . ?
N3 C11 1.354(5) . ?
N3 C12 1.451(6) . ?
N3 C13 1.456(6) . ?
N4 C16 1.354(7) . ?
N4 C17 1.453(6) 2_655 ?
N4 C18 1.470(6) . ?
C1 C17 1.535(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C6 1.538(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.453(8) . ?
C4 C5 1.176(7) . ?
C5 H5 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C11 1.544(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.449(8) . ?
C9 C10 1.189(8) . ?
C10 H10 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C16 1.523(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.462(7) . ?
C14 C15 1.184(7) . ?
C15 H15 0.9500 . ?
C17 N4 1.453(6) 2_655 ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.462(8) . ?
C19 C20 1.188(8) . ?
C20 H20 0.9500 . ?
O1S H1S 0.8400 . ?
O1S C1S 1.417(7) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 123.7(4) . . ?
C1 N1 C3 119.5(4) . . ?
C2 N1 C3 116.3(4) . . ?
C6 N2 C7 123.2(4) . . ?
C6 N2 C8 117.6(4) . . ?
C7 N2 C8 115.7(3) . . ?
C11 N3 C12 118.3(4) . . ?
C11 N3 C13 123.6(4) . . ?
C12 N3 C13 117.8(4) . . ?
C16 N4 C17 118.2(4) . 2_655 ?
C16 N4 C18 124.0(4) . . ?
C17 N4 C18 117.1(4) 2_655 . ?
O1 C1 N1 123.5(4) . . ?
O1 C1 C17 118.8(4) . . ?
N1 C1 C17 117.5(4) . . ?
N1 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
N1 C2 C6 111.2(4) . . ?
H2A C2 H2B 108.0 . . ?
C6 C2 H2A 109.4 . . ?
C6 C2 H2B 109.4 . . ?
N1 C3 H3A 108.8 . . ?
N1 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 N1 113.8(4) . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C5 C4 C3 175.0(5) . . ?
C4 C5 H5 180.0 . . ?
O2 C6 N2 122.8(4) . . ?
O2 C6 C2 121.2(4) . . ?
N2 C6 C2 116.0(4) . . ?
N2 C7 H7A 109.7 . . ?
N2 C7 H7B 109.7 . . ?
N2 C7 C11 109.7(4) . . ?
H7A C7 H7B 108.2 . . ?
C11 C7 H7A 109.7 . . ?
C11 C7 H7B 109.7 . . ?
N2 C8 H8A 109.2 . . ?
N2 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 N2 112.1(4) . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C10 C9 C8 176.9(6) . . ?
C9 C10 H10 180.0 . . ?
O3 C11 N3 122.8(4) . . ?
O3 C11 C7 121.3(4) . . ?
N3 C11 C7 115.9(4) . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
N3 C12 C16 110.9(4) . . ?
H12A C12 H12B 108.0 . . ?
C16 C12 H12A 109.5 . . ?
C16 C12 H12B 109.5 . . ?
N3 C13 H13A 108.6 . . ?
N3 C13 H13B 108.6 . . ?
N3 C13 C14 114.9(4) . . ?
H13A C13 H13B 107.5 . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C15 C14 C13 178.3(5) . . ?
C14 C15 H15 180.0 . . ?
O4 C16 N4 121.9(5) . . ?
O4 C16 C12 122.7(5) . . ?
N4 C16 C12 115.4(5) . . ?
N4 C17 C1 110.8(4) 2_655 . ?
N4 C17 H17A 109.5 2_655 . ?
N4 C17 H17B 109.5 2_655 . ?
C1 C17 H17A 109.5 . . ?
C1 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
N4 C18 H18A 108.6 . . ?
N4 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 N4 114.6(4) . . ?
C19 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
C20 C19 C18 176.0(6) . . ?
C19 C20 H20 180.0 . . ?
C1S O1S H1S 109.5 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C17 N4 -15.3(6) . . . 2_655 ?
N1 C1 C17 N4 169.1(4) . . . 2_655 ?
N1 C2 C6 O2 5.9(6) . . . . ?
N1 C2 C6 N2 -176.8(4) . . . . ?
N2 C7 C11 O3 -11.3(6) . . . . ?
N2 C7 C11 N3 167.4(4) . . . . ?
N3 C12 C16 O4 0.6(6) . . . . ?
N3 C12 C16 N4 179.0(4) . . . . ?
C1 N1 C2 C6 86.1(5) . . . . ?
C1 N1 C3 C4 118.7(5) . . . . ?
C2 N1 C1 O1 -178.5(4) . . . . ?
C2 N1 C1 C17 -3.1(7) . . . . ?
C2 N1 C3 C4 -68.4(6) . . . . ?
C3 N1 C1 O1 -6.2(7) . . . . ?
C3 N1 C1 C17 169.1(4) . . . . ?
C3 N1 C2 C6 -86.3(5) . . . . ?
C6 N2 C7 C11 76.8(5) . . . . ?
C6 N2 C8 C9 137.1(4) . . . . ?
C7 N2 C6 O2 -167.8(4) . . . . ?
C7 N2 C6 C2 15.0(6) . . . . ?
C7 N2 C8 C9 -63.3(5) . . . . ?
C8 N2 C6 O2 -9.8(6) . . . . ?
C8 N2 C6 C2 173.0(4) . . . . ?
C8 N2 C7 C11 -81.6(5) . . . . ?
C11 N3 C12 C16 -84.3(5) . . . . ?
C11 N3 C13 C14 -91.7(5) . . . . ?
C12 N3 C11 O3 2.5(7) . . . . ?
C12 N3 C11 C7 -176.1(4) . . . . ?
C12 N3 C13 C14 93.0(5) . . . . ?
C13 N3 C11 O3 -172.7(4) . . . . ?
C13 N3 C11 C7 8.7(6) . . . . ?
C13 N3 C12 C16 91.1(5) . . . . ?
C16 N4 C18 C19 -86.5(6) . . . . ?
C17 N4 C16 O4 1.8(7) 2_655 . . . ?
C17 N4 C16 C12 -176.7(4) 2_655 . . . ?
C17 N4 C18 C19 103.3(5) 2_655 . . . ?
C18 N4 C16 O4 -168.3(4) . . . . ?
C18 N4 C16 C12 13.3(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
