# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_71sd
_database_code_depnum_ccdc_archive 'CCDC 1015722'
_audit_update_record             
;
2014-07-24 deposited with the CCDC.
2015-04-01 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         "C32 H36 N4 O10','C2 H6 O1 S1"
_chemical_formula_sum            'C34 H42 N4 O11 S1'
_chemical_formula_weight         714.77

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'

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

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

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

_cell_length_a                   8.6053(13)
_cell_length_b                   18.642(3)
_cell_length_c                   12.190(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.319(5)
_cell_angle_gamma                90
_cell_volume                     1934.9(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1781
_cell_measurement_theta_min      2.630
_cell_measurement_theta_max      24.821

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             756
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.143
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4843
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11865
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.011
_diffrn_reflns_theta_max         23.257
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.786
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.786
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.786
_reflns_number_total             2759
_reflns_number_gt                1944
_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       'KAPPA APEX II (BRUKER-AXS)'
_computing_cell_refinement       'SAINTPLUS (BRUKER-AXS)'
_computing_data_reduction        'SAINTPLUS (BRUKER-AXS)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0882P)²+2.7122P]
 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         2759
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0622
_refine_ls_wR_factor_ref         0.1781
_refine_ls_wR_factor_gt          0.1601
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
S1 S 0.00394(16) 0.08610(7) 0.83919(11) 0.0387(4) Uani 1 1 d . . . . .
O2 O 0.0209(3) 0.53344(15) 0.8405(2) 0.0231(7) Uani 1 1 d . . . . .
O3 O 0.3687(3) 0.30045(15) 0.9072(2) 0.0242(7) Uani 1 1 d . . . . .
O1 O 0.1356(3) 0.32118(15) 0.6991(2) 0.0236(7) Uani 1 1 d . . . . .
O4 O 0.7386(3) 0.26204(16) 0.8868(3) 0.0280(8) Uani 1 1 d . . . . .
O5 O 0.6755(3) 0.36393(15) 0.9681(2) 0.0264(8) Uani 1 1 d . . . . .
N1 N 0.1280(4) 0.43405(17) 0.7695(3) 0.0163(8) Uani 1 1 d . . . . .
N2 N 0.4433(4) 0.38920(18) 0.7989(3) 0.0192(8) Uani 1 1 d . . . . .
H2 H 0.4239 0.4327 0.7722 0.023 Uiso 1 1 calc R U . . .
C9 C 0.3437(5) 0.3588(2) 0.8613(3) 0.0207(10) Uani 1 1 d . . . . .
C6 C 0.0201(4) 0.4863(2) 0.5545(3) 0.0163(9) Uani 1 1 d . . . . .
C2 C 0.0530(5) 0.5016(2) 0.7601(3) 0.0199(10) Uani 1 1 d . . . . .
C1 C 0.1098(4) 0.3847(2) 0.6820(3) 0.0203(10) Uani 1 1 d . . . . .
C3 C 0.0616(5) 0.4131(2) 0.5675(3) 0.0195(10) Uani 1 1 d . . . . .
O6 O 0.1039(4) 0.03871(17) 0.7788(3) 0.0380(9) Uani 1 1 d . . . . .
C8 C 0.2039(5) 0.4066(2) 0.8810(3) 0.0196(10) Uani 1 1 d . . . . .
C5 C 0.0628(5) 0.3701(2) 0.4773(4) 0.0253(11) Uani 1 1 d . . . . .
H5 H 0.0890 0.3208 0.4872 0.030 Uiso 1 1 calc R U . . .
C4 C 0.0154(4) 0.5313(2) 0.6458(3) 0.0193(10) Uani 1 1 d . . . . .
C7 C 0.0255(5) 0.3980(2) 0.3696(3) 0.0236(10) Uani 1 1 d . . . . .
H7 H 0.0287 0.3677 0.3073 0.028 Uiso 1 1 calc R U . . .
C13 C 0.0834(5) 0.3643(2) 0.9356(3) 0.0240(10) Uani 1 1 d . . . . .
H13A H -0.0038 0.3959 0.9471 0.036 Uiso 1 1 calc R U . . .
H13B H 0.1334 0.3456 1.0072 0.036 Uiso 1 1 calc R U . . .
H13C H 0.0433 0.3243 0.8875 0.036 Uiso 1 1 calc R U . . .
C15 C 0.5376(6) 0.2914(3) 0.6922(4) 0.0322(12) Uani 1 1 d . . . . .
H15A H 0.4809 0.3118 0.6238 0.048 Uiso 1 1 calc R U . . .
H15B H 0.4701 0.2569 0.7233 0.048 Uiso 1 1 calc R U . . .
H15C H 0.6326 0.2670 0.6758 0.048 Uiso 1 1 calc R U . . .
C11 C 0.6718(5) 0.3195(2) 0.8825(4) 0.0230(10) Uani 1 1 d . . . . .
C10 C 0.5831(5) 0.3509(2) 0.7750(3) 0.0230(10) Uani 1 1 d . . . . .
C14 C 0.2779(5) 0.4669(2) 0.9570(3) 0.0244(11) Uani 1 1 d . . . . .
H14A H 0.1956 0.4999 0.9735 0.037 Uiso 1 1 calc R U . . .
H14B H 0.3540 0.4932 0.9198 0.037 Uiso 1 1 calc R U . . .
H14C H 0.3313 0.4462 1.0262 0.037 Uiso 1 1 calc R U . . .
C16 C 0.6929(5) 0.4055(2) 0.7302(4) 0.0303(11) Uani 1 1 d . . . . .
H16A H 0.6392 0.4268 0.6615 0.045 Uiso 1 1 calc R U . . .
H16B H 0.7884 0.3810 0.7151 0.045 Uiso 1 1 calc R U . . .
H16C H 0.7210 0.4433 0.7854 0.045 Uiso 1 1 calc R U . . .
C12 C 0.7476(6) 0.3358(2) 1.0743(4) 0.0299(11) Uani 1 1 d . . . . .
H12A H 0.7448 0.3724 1.1317 0.045 Uiso 1 1 calc R U . . .
H12B H 0.8569 0.3227 1.0701 0.045 Uiso 1 1 calc R U . . .
H12C H 0.6898 0.2933 1.0929 0.045 Uiso 1 1 calc R U . . .
C17 C -0.1273(6) 0.1313(3) 0.7376(5) 0.0515(16) Uani 1 1 d . . . . .
H17A H -0.2031 0.0970 0.6997 0.077 Uiso 1 1 calc R U . . .
H17B H -0.0684 0.1536 0.6835 0.077 Uiso 1 1 calc R U . . .
H17C H -0.1834 0.1685 0.7731 0.077 Uiso 1 1 calc R U . . .
C18 C 0.1206(6) 0.1616(3) 0.8881(4) 0.0444(14) Uani 1 1 d . . . . .
H18A H 0.2031 0.1465 0.9476 0.067 Uiso 1 1 calc R U . . .
H18B H 0.0542 0.1978 0.9165 0.067 Uiso 1 1 calc R U . . .
H18C H 0.1688 0.1820 0.8271 0.067 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
S1 O6 1.498(3) . ?
S1 C17 1.765(5) . ?
S1 C18 1.781(5) . ?
O2 C2 1.211(5) . ?
O3 C9 1.228(5) . ?
O1 C1 1.217(5) . ?
O4 C11 1.213(5) . ?
O5 C11 1.329(5) . ?
O5 C12 1.450(5) . ?
N1 C1 1.400(5) . ?
N1 C2 1.411(5) . ?
N1 C8 1.510(5) . ?
N2 C9 1.350(5) . ?
N2 C10 1.464(5) . ?
N2 H2 0.8800 . ?
C9 C8 1.544(6) . ?
C6 C4 1.398(5) . ?
C6 C3 1.414(6) . ?
C6 C6 1.419(8) 3_566 ?
C2 C4 1.491(6) . ?
C1 C3 1.495(6) . ?
C3 C5 1.362(6) . ?
C8 C13 1.529(6) . ?
C8 C14 1.535(6) . ?
C5 C7 1.404(6) . ?
C5 H5 0.9500 . ?
C4 C7 1.370(6) 3_566 ?
C7 C4 1.370(6) 3_566 ?
C7 H7 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 C10 1.513(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C11 C10 1.534(6) . ?
C10 C16 1.542(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
O6 S1 C17 107.0(2) . . ?
O6 S1 C18 107.1(2) . . ?
C17 S1 C18 97.5(3) . . ?
C11 O5 C12 115.7(3) . . ?
C1 N1 C2 121.7(3) . . ?
C1 N1 C8 116.7(3) . . ?
C2 N1 C8 120.5(3) . . ?
C9 N2 C10 120.9(3) . . ?
C9 N2 H2 119.5 . . ?
C10 N2 H2 119.5 . . ?
O3 C9 N2 123.0(4) . . ?
O3 C9 C8 122.0(4) . . ?
N2 C9 C8 114.7(4) . . ?
C4 C6 C3 121.7(4) . . ?
C4 C6 C6 120.0(5) . 3_566 ?
C3 C6 C6 118.3(4) . 3_566 ?
O2 C2 N1 121.8(4) . . ?
O2 C2 C4 121.9(4) . . ?
N1 C2 C4 116.2(4) . . ?
O1 C1 N1 120.8(4) . . ?
O1 C1 C3 121.5(4) . . ?
N1 C1 C3 117.7(4) . . ?
C5 C3 C6 120.6(4) . . ?
C5 C3 C1 120.9(4) . . ?
C6 C3 C1 118.5(4) . . ?
N1 C8 C13 109.5(3) . . ?
N1 C8 C14 112.5(3) . . ?
C13 C8 C14 111.3(3) . . ?
N1 C8 C9 107.5(3) . . ?
C13 C8 C9 111.3(3) . . ?
C14 C8 C9 104.6(3) . . ?
C3 C5 C7 120.7(4) . . ?
C3 C5 H5 119.7 . . ?
C7 C5 H5 119.7 . . ?
C7 C4 C6 120.2(4) 3_566 . ?
C7 C4 C2 120.2(4) 3_566 . ?
C6 C4 C2 119.6(4) . . ?
C4 C7 C5 120.2(4) 3_566 . ?
C4 C7 H7 119.9 3_566 . ?
C5 C7 H7 119.9 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C11 O5 124.0(4) . . ?
O4 C11 C10 123.2(4) . . ?
O5 C11 C10 112.6(4) . . ?
N2 C10 C15 110.5(3) . . ?
N2 C10 C11 109.8(3) . . ?
C15 C10 C11 109.8(4) . . ?
N2 C10 C16 108.2(3) . . ?
C15 C10 C16 111.1(4) . . ?
C11 C10 C16 107.4(3) . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
S1 C18 H18A 109.5 . . ?
S1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
S1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C10 N2 C9 O3 5.0(6) . . . . ?
C10 N2 C9 C8 178.7(3) . . . . ?
C1 N1 C2 O2 153.7(4) . . . . ?
C8 N1 C2 O2 -14.0(6) . . . . ?
C1 N1 C2 C4 -26.2(5) . . . . ?
C8 N1 C2 C4 166.1(3) . . . . ?
C2 N1 C1 O1 -159.0(4) . . . . ?
C8 N1 C1 O1 9.1(5) . . . . ?
C2 N1 C1 C3 22.4(5) . . . . ?
C8 N1 C1 C3 -169.4(3) . . . . ?
C4 C6 C3 C5 178.9(4) . . . . ?
C6 C6 C3 C5 0.0(7) 3_566 . . . ?
C4 C6 C3 C1 -3.3(6) . . . . ?
C6 C6 C3 C1 177.7(4) 3_566 . . . ?
O1 C1 C3 C5 -7.7(6) . . . . ?
N1 C1 C3 C5 170.8(4) . . . . ?
O1 C1 C3 C6 174.5(4) . . . . ?
N1 C1 C3 C6 -7.0(5) . . . . ?
C1 N1 C8 C13 -78.6(4) . . . . ?
C2 N1 C8 C13 89.6(4) . . . . ?
C1 N1 C8 C14 157.0(3) . . . . ?
C2 N1 C8 C14 -34.7(5) . . . . ?
C1 N1 C8 C9 42.4(4) . . . . ?
C2 N1 C8 C9 -149.4(3) . . . . ?
O3 C9 C8 N1 -135.4(4) . . . . ?
N2 C9 C8 N1 50.8(4) . . . . ?
O3 C9 C8 C13 -15.5(5) . . . . ?
N2 C9 C8 C13 170.7(3) . . . . ?
O3 C9 C8 C14 104.8(4) . . . . ?
N2 C9 C8 C14 -69.0(4) . . . . ?
C6 C3 C5 C7 1.2(6) . . . . ?
C1 C3 C5 C7 -176.6(4) . . . . ?
C3 C6 C4 C7 -179.9(4) . . . 3_566 ?
C6 C6 C4 C7 -0.9(7) 3_566 . . 3_566 ?
C3 C6 C4 C2 -0.8(6) . . . . ?
C6 C6 C4 C2 178.1(4) 3_566 . . . ?
O2 C2 C4 C7 14.2(6) . . . 3_566 ?
N1 C2 C4 C7 -165.9(4) . . . 3_566 ?
O2 C2 C4 C6 -164.9(4) . . . . ?
N1 C2 C4 C6 15.0(5) . . . . ?
C3 C5 C7 C4 -1.2(7) . . . 3_566 ?
C12 O5 C11 O4 -8.3(6) . . . . ?
C12 O5 C11 C10 175.7(3) . . . . ?
C9 N2 C10 C15 73.0(5) . . . . ?
C9 N2 C10 C11 -48.3(5) . . . . ?
C9 N2 C10 C16 -165.2(4) . . . . ?
O4 C11 C10 N2 143.8(4) . . . . ?
O5 C11 C10 N2 -40.2(5) . . . . ?
O4 C11 C10 C15 22.1(6) . . . . ?
O5 C11 C10 C15 -161.8(4) . . . . ?
O4 C11 C10 C16 -98.8(5) . . . . ?
O5 C11 C10 C16 77.3(4) . . . . ?

_refine_diff_density_max         0.649
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.077

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
####################################################################### 
# 
# 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_tgmp73
_database_code_depnum_ccdc_archive 'CCDC 1015723'
_audit_update_record             
;
2014-07-24 deposited with the CCDC.
2015-04-01 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H28 N4 O10'
_chemical_formula_sum            'C28 H28 N4 O10'
_chemical_formula_weight         580.54

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

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

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

_cell_length_a                   9.942(5)
_cell_length_b                   14.412(5)
_cell_length_c                   18.805(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2694.5(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1704
_cell_measurement_theta_min      2.489
_cell_measurement_theta_max      21.312

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6028
_exptl_absorpt_correction_T_max  0.7447
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8117
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.780
_diffrn_reflns_theta_max         17.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.398
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.398
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.383
_reflns_number_total             1864
_reflns_number_gt                1559
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.362

_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       'KAPPA APEX II (BRUKER-AXS)'
_computing_cell_refinement       'SAINTPLUS (BRUKER-AXS)'
_computing_data_reduction        'SAINTPLUS (BRUKER-AXS)'
_computing_structure_solution    
'SIR92 (Altomare A., Cascarano G., Giacovazzo C. and Guagliardi A. (1993). J. Appl. Cryst. 26, 343-350)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0907P)²+18.1835P]
 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_abs_structure_details 
;
 Flack x determined using 586 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -1.8(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         1864
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0768
_refine_ls_wR_factor_ref         0.2021
_refine_ls_wR_factor_gt          0.1848
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.5599(10) 0.7170(6) 0.6476(6) 0.026(3) Uani 1 1 d . . . . .
O2 O 0.3976(10) 0.3384(6) 0.6422(6) 0.030(3) Uani 1 1 d . . . . .
O3 O 1.3159(10) -0.0046(7) 0.8225(5) 0.027(3) Uiso 1 1 d . . . . .
O4 O 0.1814(10) 0.5413(7) 0.6570(5) 0.028(3) Uiso 1 1 d . . . . .
O5 O 1.0881(11) 0.2341(7) 0.8814(6) 0.035(3) Uani 1 1 d . . . . .
O6 O 0.5176(10) 0.7341(7) 0.5328(5) 0.031(3) Uiso 1 1 d . . . . .
O7 O 0.4839(10) 0.4809(7) 0.8511(6) 0.034(3) Uani 1 1 d . . . . .
O8 O 0.9901(11) 0.0704(7) 0.6836(6) 0.039(3) Uani 1 1 d . . . . .
N9 N 0.4413(11) 0.4071(8) 0.7472(6) 0.020(3) Uiso 1 1 d . . . . .
N10 N 0.4070(13) 0.5593(9) 0.6521(6) 0.026(3) Uiso 1 1 d . . . . .
H10 H 0.4867 0.5477 0.6704 0.031 Uiso 1 1 calc R U . . .
O11 O 1.2597(12) 0.0095(8) 0.9798(6) 0.046(3) Uiso 1 1 d . . . . .
N12 N 1.0986(13) -0.0018(9) 0.8557(6) 0.029(4) Uiso 1 1 d . . . . .
H12 H 1.0189 0.0242 0.8517 0.035 Uiso 1 1 calc R U . . .
O13 O 1.2812(12) -0.1482(8) 0.9744(6) 0.044(3) Uiso 1 1 d . . . . .
C14 C 0.8018(15) 0.2548(11) 0.7677(7) 0.021(4) Uiso 1 1 d . . . . .
N15 N 1.0475(13) 0.1625(9) 0.7784(6) 0.025(4) Uiso 1 1 d . . . . .
C16 C 0.5977(15) 0.2897(10) 0.7016(8) 0.017(4) Uiso 1 1 d . . . . .
C17 C 0.8331(16) 0.1904(11) 0.7165(8) 0.028(5) Uiso 1 1 d . . . . .
C18 C 0.4678(17) 0.3485(11) 0.6940(9) 0.023(4) Uiso 1 1 d . . . . .
C19 C 0.3965(16) 0.6196(10) 0.5917(7) 0.026(4) Uiso 1 1 d . . . . .
H19 H 0.3066 0.6506 0.5945 0.031 Uiso 1 1 calc R U . . .
C20 C 0.6777(15) 0.3065(10) 0.7592(7) 0.018(4) Uiso 1 1 d . . . . .
C21 C 1.2027(16) 0.0324(10) 0.8190(7) 0.022(4) Uiso 1 1 d . . . . .
C22 C 0.5027(17) 0.6960(10) 0.5943(9) 0.021(4) Uiso 1 1 d . . . . .
C23 C 1.0165(18) 0.2202(11) 0.8309(9) 0.028(4) Uiso 1 1 d . . . . .
C24 C 0.2969(16) 0.5199(10) 0.6816(7) 0.020(4) Uiso 1 1 d . . . . .
C25 C 0.6478(15) 0.3702(11) 0.8108(8) 0.022(4) Uiso 1 1 d . . . . .
C26 C 0.7295(16) 0.3850(11) 0.8680(8) 0.027(4) Uiso 1 1 d . . . . .
H26 H 0.7038 0.4290 0.9030 0.033 Uiso 1 1 calc R U . . .
C27 C 0.6281(16) 0.2227(10) 0.6528(8) 0.026(4) Uiso 1 1 d . . . . .
H27 H 0.5690 0.2098 0.6144 0.031 Uiso 1 1 calc R U . . .
C28 C 0.1878(17) 0.3899(11) 0.7509(8) 0.038(5) Uiso 1 1 d . . . . .
H28A H 0.2012 0.3511 0.7931 0.057 Uiso 1 1 calc R U . . .
H28B H 0.1820 0.3504 0.7086 0.057 Uiso 1 1 calc R U . . .
H28C H 0.1044 0.4255 0.7560 0.057 Uiso 1 1 calc R U . . .
C29 C 0.3081(15) 0.4577(10) 0.7429(7) 0.022(4) Uiso 1 1 d . . . . .
H29 H 0.3050 0.4987 0.7858 0.027 Uiso 1 1 calc R U . . .
C30 C 0.5196(17) 0.4251(13) 0.8062(8) 0.028(4) Uiso 1 1 d . . . . .
C31 C 1.1891(16) 0.1231(11) 0.7801(8) 0.027(4) Uiso 1 1 d . . . . .
H31 H 1.2393 0.1678 0.8110 0.033 Uiso 1 1 calc R U . . .
C32 C 0.8835(17) 0.2733(11) 0.8243(8) 0.028(4) Uiso 1 1 d . . . . .
C33 C 1.2234(18) -0.0652(14) 0.9528(9) 0.046(5) Uiso 1 1 d . . . . .
C34 C 1.2626(16) 0.1267(11) 0.7121(8) 0.030(4) Uiso 1 1 d . . . . .
H34A H 1.2509 0.1880 0.6905 0.046 Uiso 1 1 calc R U . . .
H34B H 1.2272 0.0791 0.6800 0.046 Uiso 1 1 calc R U . . .
H34C H 1.3584 0.1154 0.7207 0.046 Uiso 1 1 calc R U . . .
C35 C 0.6172(17) 0.8108(12) 0.5292(9) 0.039(5) Uiso 1 1 d . . . . .
H35A H 0.6213 0.8350 0.4806 0.058 Uiso 1 1 calc R U . . .
H35B H 0.7060 0.7874 0.5431 0.058 Uiso 1 1 calc R U . . .
H35C H 0.5902 0.8605 0.5617 0.058 Uiso 1 1 calc R U . . .
C36 C 0.7512(17) 0.1725(11) 0.6611(8) 0.034(5) Uiso 1 1 d . . . . .
H36 H 0.7752 0.1264 0.6274 0.041 Uiso 1 1 calc R U . . .
C37 C 0.3984(17) 0.5623(12) 0.5225(8) 0.040(5) Uiso 1 1 d . . . . .
H37A H 0.3268 0.5156 0.5241 0.060 Uiso 1 1 calc R U . . .
H37B H 0.4857 0.5313 0.5177 0.060 Uiso 1 1 calc R U . . .
H37C H 0.3840 0.6035 0.4818 0.060 Uiso 1 1 calc R U . . .
C38 C 0.9642(17) 0.1342(13) 0.7242(9) 0.035(5) Uiso 1 1 d . . . . .
C39 C 1.1156(16) -0.0804(12) 0.9017(8) 0.032(5) Uiso 1 1 d . . . . .
H39 H 1.1347 -0.1372 0.8728 0.038 Uiso 1 1 calc R U . . .
C40 C 0.8505(16) 0.3361(11) 0.8760(8) 0.027(5) Uiso 1 1 d . . . . .
H40 H 0.9075 0.3463 0.9157 0.033 Uiso 1 1 calc R U . . .
C41 C 1.388(2) -0.1445(14) 1.0266(10) 0.058(6) Uiso 1 1 d . . . . .
H41A H 1.4203 -0.2075 1.0365 0.086 Uiso 1 1 calc R U . . .
H41B H 1.3544 -0.1164 1.0705 0.086 Uiso 1 1 calc R U . . .
H41C H 1.4627 -0.1070 1.0080 0.086 Uiso 1 1 calc R U . . .
C42 C 0.987(2) -0.0954(14) 0.9471(10) 0.064(6) Uiso 1 1 d . . . . .
H42A H 0.9100 -0.1057 0.9157 0.097 Uiso 1 1 calc R U . . .
H42B H 0.9710 -0.0404 0.9765 0.097 Uiso 1 1 calc R U . . .
H42C H 0.9995 -0.1497 0.9778 0.097 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 C22 1.192(17) . ?
O2 C18 1.207(17) . ?
O3 C21 1.248(16) . ?
O4 C24 1.276(16) . ?
O5 C23 1.204(18) . ?
O6 C22 1.290(17) . ?
O6 C35 1.485(19) . ?
O7 C30 1.220(18) . ?
O8 C38 1.222(19) . ?
N9 C18 1.334(18) . ?
N9 C30 1.379(18) . ?
N9 C29 1.514(18) . ?
N10 C24 1.351(18) . ?
N10 C19 1.434(18) . ?
N10 H10 0.8800 . ?
O11 C33 1.24(2) . ?
N12 C21 1.338(18) . ?
N12 C39 1.435(19) . ?
N12 H12 0.8800 . ?
O13 C33 1.39(2) . ?
O13 C41 1.45(2) . ?
C14 C32 1.37(2) . ?
C14 C17 1.37(2) . ?
C14 C20 1.45(2) . ?
N15 C23 1.325(19) . ?
N15 C38 1.376(19) . ?
N15 C31 1.519(19) . ?
C16 C27 1.36(2) . ?
C16 C20 1.367(19) . ?
C16 C18 1.55(2) . ?
C17 C36 1.35(2) . ?
C17 C38 1.54(2) . ?
C19 C22 1.53(2) . ?
C19 C37 1.54(2) . ?
C19 H19 1.0000 . ?
C20 C25 1.367(19) . ?
C21 C31 1.50(2) . ?
C23 C32 1.53(2) . ?
C24 C29 1.47(2) . ?
C25 C26 1.37(2) . ?
C25 C30 1.50(2) . ?
C26 C40 1.40(2) . ?
C26 H26 0.9500 . ?
C27 C36 1.43(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.55(2) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29 1.0000 . ?
C31 C34 1.47(2) . ?
C31 H31 1.0000 . ?
C32 C40 1.37(2) . ?
C33 C39 1.46(2) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C39 C42 1.55(2) . ?
C39 H39 1.0000 . ?
C40 H40 0.9500 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 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
C22 O6 C35 115.7(12) . . ?
C18 N9 C30 127.6(14) . . ?
C18 N9 C29 115.9(12) . . ?
C30 N9 C29 116.4(12) . . ?
C24 N10 C19 121.3(13) . . ?
C24 N10 H10 119.3 . . ?
C19 N10 H10 119.3 . . ?
C21 N12 C39 120.7(13) . . ?
C21 N12 H12 119.6 . . ?
C39 N12 H12 119.6 . . ?
C33 O13 C41 118.2(14) . . ?
C32 C14 C17 122.9(14) . . ?
C32 C14 C20 119.4(13) . . ?
C17 C14 C20 117.6(13) . . ?
C23 N15 C38 126.7(15) . . ?
C23 N15 C31 115.7(13) . . ?
C38 N15 C31 117.6(13) . . ?
C27 C16 C20 122.0(14) . . ?
C27 C16 C18 120.6(14) . . ?
C20 C16 C18 117.4(13) . . ?
C36 C17 C14 122.3(15) . . ?
C36 C17 C38 118.9(14) . . ?
C14 C17 C38 118.8(14) . . ?
O2 C18 N9 124.5(15) . . ?
O2 C18 C16 119.3(13) . . ?
N9 C18 C16 116.2(14) . . ?
N10 C19 C22 111.2(12) . . ?
N10 C19 C37 110.1(12) . . ?
C22 C19 C37 113.9(13) . . ?
N10 C19 H19 107.1 . . ?
C22 C19 H19 107.1 . . ?
C37 C19 H19 107.1 . . ?
C25 C20 C16 123.7(14) . . ?
C25 C20 C14 116.9(13) . . ?
C16 C20 C14 119.4(13) . . ?
O3 C21 N12 120.8(13) . . ?
O3 C21 C31 118.6(14) . . ?
N12 C21 C31 120.1(14) . . ?
O1 C22 O6 126.2(15) . . ?
O1 C22 C19 122.7(14) . . ?
O6 C22 C19 111.0(14) . . ?
O5 C23 N15 123.7(16) . . ?
O5 C23 C32 119.4(14) . . ?
N15 C23 C32 117.0(16) . . ?
O4 C24 N10 118.6(13) . . ?
O4 C24 C29 120.1(14) . . ?
N10 C24 C29 121.2(14) . . ?
C20 C25 C26 122.3(14) . . ?
C20 C25 C30 119.8(14) . . ?
C26 C25 C30 117.9(14) . . ?
C25 C26 C40 121.1(15) . . ?
C25 C26 H26 119.5 . . ?
C40 C26 H26 119.5 . . ?
C16 C27 C36 118.3(15) . . ?
C16 C27 H27 120.9 . . ?
C36 C27 H27 120.9 . . ?
C29 C28 H28A 109.5 . . ?
C29 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C29 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C24 C29 N9 113.8(12) . . ?
C24 C29 C28 113.7(13) . . ?
N9 C29 C28 111.5(11) . . ?
C24 C29 H29 105.7 . . ?
N9 C29 H29 105.7 . . ?
C28 C29 H29 105.7 . . ?
O7 C30 N9 121.2(15) . . ?
O7 C30 C25 123.7(14) . . ?
N9 C30 C25 115.1(15) . . ?
C34 C31 C21 114.1(13) . . ?
C34 C31 N15 115.4(12) . . ?
C21 C31 N15 114.7(13) . . ?
C34 C31 H31 103.5 . . ?
C21 C31 H31 103.5 . . ?
N15 C31 H31 103.5 . . ?
C14 C32 C40 122.7(15) . . ?
C14 C32 C23 118.6(14) . . ?
C40 C32 C23 118.7(15) . . ?
O11 C33 O13 120.4(15) . . ?
O11 C33 C39 127.8(17) . . ?
O13 C33 C39 111.6(16) . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O6 C35 H35A 109.5 . . ?
O6 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O6 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C17 C36 C27 120.4(15) . . ?
C17 C36 H36 119.8 . . ?
C27 C36 H36 119.8 . . ?
C19 C37 H37A 109.5 . . ?
C19 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C19 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O8 C38 N15 124.0(16) . . ?
O8 C38 C17 121.0(15) . . ?
N15 C38 C17 115.0(15) . . ?
N12 C39 C33 111.4(14) . . ?
N12 C39 C42 110.2(14) . . ?
C33 C39 C42 105.3(13) . . ?
N12 C39 H39 110.0 . . ?
C33 C39 H39 110.0 . . ?
C42 C39 H39 110.0 . . ?
C32 C40 C26 117.5(15) . . ?
C32 C40 H40 121.2 . . ?
C26 C40 H40 121.2 . . ?
O13 C41 H41A 109.5 . . ?
O13 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
O13 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 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
C32 C14 C17 C36 179.7(15) . . . . ?
C20 C14 C17 C36 -2(2) . . . . ?
C32 C14 C17 C38 2(2) . . . . ?
C20 C14 C17 C38 -179.9(13) . . . . ?
C30 N9 C18 O2 -176.9(14) . . . . ?
C29 N9 C18 O2 5(2) . . . . ?
C30 N9 C18 C16 4(2) . . . . ?
C29 N9 C18 C16 -174.5(11) . . . . ?
C27 C16 C18 O2 -4(2) . . . . ?
C20 C16 C18 O2 176.8(14) . . . . ?
C27 C16 C18 N9 174.9(14) . . . . ?
C20 C16 C18 N9 -4(2) . . . . ?
C24 N10 C19 C22 146.3(13) . . . . ?
C24 N10 C19 C37 -86.6(17) . . . . ?
C27 C16 C20 C25 -177.1(14) . . . . ?
C18 C16 C20 C25 2(2) . . . . ?
C27 C16 C20 C14 3(2) . . . . ?
C18 C16 C20 C14 -178.6(13) . . . . ?
C32 C14 C20 C25 -2(2) . . . . ?
C17 C14 C20 C25 179.8(14) . . . . ?
C32 C14 C20 C16 178.3(14) . . . . ?
C17 C14 C20 C16 0(2) . . . . ?
C39 N12 C21 O3 2(2) . . . . ?
C39 N12 C21 C31 -170.5(13) . . . . ?
C35 O6 C22 O1 1(2) . . . . ?
C35 O6 C22 C19 179.0(11) . . . . ?
N10 C19 C22 O1 -19(2) . . . . ?
C37 C19 C22 O1 -143.9(15) . . . . ?
N10 C19 C22 O6 162.7(12) . . . . ?
C37 C19 C22 O6 37.7(18) . . . . ?
C38 N15 C23 O5 171.0(15) . . . . ?
C31 N15 C23 O5 -8(2) . . . . ?
C38 N15 C23 C32 -11(2) . . . . ?
C31 N15 C23 C32 170.3(12) . . . . ?
C19 N10 C24 O4 -4(2) . . . . ?
C19 N10 C24 C29 179.5(12) . . . . ?
C16 C20 C25 C26 179.6(14) . . . . ?
C14 C20 C25 C26 0(2) . . . . ?
C16 C20 C25 C30 1(2) . . . . ?
C14 C20 C25 C30 -178.9(13) . . . . ?
C20 C25 C26 C40 1(2) . . . . ?
C30 C25 C26 C40 179.9(14) . . . . ?
C20 C16 C27 C36 -3(2) . . . . ?
C18 C16 C27 C36 178.1(13) . . . . ?
O4 C24 C29 N9 155.5(13) . . . . ?
N10 C24 C29 N9 -27.7(18) . . . . ?
O4 C24 C29 C28 26.5(19) . . . . ?
N10 C24 C29 C28 -156.8(13) . . . . ?
C18 N9 C29 C24 -63.7(16) . . . . ?
C30 N9 C29 C24 117.7(14) . . . . ?
C18 N9 C29 C28 66.5(16) . . . . ?
C30 N9 C29 C28 -112.1(14) . . . . ?
C18 N9 C30 O7 179.7(14) . . . . ?
C29 N9 C30 O7 -2(2) . . . . ?
C18 N9 C30 C25 -1(2) . . . . ?
C29 N9 C30 C25 177.0(12) . . . . ?
C20 C25 C30 O7 177.6(14) . . . . ?
C26 C25 C30 O7 -1(2) . . . . ?
C20 C25 C30 N9 -1(2) . . . . ?
C26 C25 C30 N9 -179.9(13) . . . . ?
O3 C21 C31 C34 43.5(19) . . . . ?
N12 C21 C31 C34 -144.1(14) . . . . ?
O3 C21 C31 N15 179.7(12) . . . . ?
N12 C21 C31 N15 -8(2) . . . . ?
C23 N15 C31 C34 -132.7(14) . . . . ?
C38 N15 C31 C34 48.3(19) . . . . ?
C23 N15 C31 C21 91.6(16) . . . . ?
C38 N15 C31 C21 -87.4(16) . . . . ?
C17 C14 C32 C40 -178.6(15) . . . . ?
C20 C14 C32 C40 3(2) . . . . ?
C17 C14 C32 C23 0(2) . . . . ?
C20 C14 C32 C23 -177.9(13) . . . . ?
O5 C23 C32 C14 -178.1(15) . . . . ?
N15 C23 C32 C14 4(2) . . . . ?
O5 C23 C32 C40 1(2) . . . . ?
N15 C23 C32 C40 -177.5(14) . . . . ?
C41 O13 C33 O11 -3(2) . . . . ?
C41 O13 C33 C39 -178.7(13) . . . . ?
C14 C17 C36 C27 2(2) . . . . ?
C38 C17 C36 C27 179.4(14) . . . . ?
C16 C27 C36 C17 1(2) . . . . ?
C23 N15 C38 O8 -168.2(15) . . . . ?
C31 N15 C38 O8 11(2) . . . . ?
C23 N15 C38 C17 13(2) . . . . ?
C31 N15 C38 C17 -168.4(13) . . . . ?
C36 C17 C38 O8 -5(2) . . . . ?
C14 C17 C38 O8 173.2(15) . . . . ?
C36 C17 C38 N15 174.5(14) . . . . ?
C14 C17 C38 N15 -8(2) . . . . ?
C21 N12 C39 C33 54.0(18) . . . . ?
C21 N12 C39 C42 170.5(13) . . . . ?
O11 C33 C39 N12 31(2) . . . . ?
O13 C33 C39 N12 -153.0(13) . . . . ?
O11 C33 C39 C42 -88(2) . . . . ?
O13 C33 C39 C42 87.6(17) . . . . ?
C14 C32 C40 C26 -2(2) . . . . ?
C23 C32 C40 C26 178.9(13) . . . . ?
C25 C26 C40 C32 0(2) . . . . ?

_refine_diff_density_max         0.460
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.083

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
####################################################################### 
# 
# 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_tgmp115
_database_code_depnum_ccdc_archive 'CCDC 1015724'
_audit_update_record             
;
2014-07-24 deposited with the CCDC.
2015-04-01 downloaded from the CCDC.
;

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

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H28 N4 O10'
_chemical_formula_sum            'C28 H28 N4 O10'
_chemical_formula_weight         580.54

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

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

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

_cell_length_a                   9.9943(15)
_cell_length_b                   14.470(2)
_cell_length_c                   18.796(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2718.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3084
_cell_measurement_theta_min      2.308
_cell_measurement_theta_max      24.5375

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6608
_exptl_absorpt_correction_T_max  0.7329
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11662
_diffrn_reflns_av_unetI/netI     0.0797
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.776
_diffrn_reflns_theta_max         21.726
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.668
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.668
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.651
_reflns_number_total             3194
_reflns_number_gt                2558
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    0.629

_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       'KAPPA APEX II (BRUKER-AXS)'
_computing_cell_refinement       'SAINTPLUS (BRUKER-AXS)'
_computing_data_reduction        'SAINTPLUS (BRUKER-AXS)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0519P)²+1.0964P]
 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_abs_structure_details 
;
 Flack x determined using 908 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -1.1(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3194
_refine_ls_number_parameters     379
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.060
_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
O9 O 0.0625(5) 0.7157(3) 0.8514(3) 0.0249(12) Uani 1 1 d . . . . .
O8 O -0.3184(5) 0.5406(3) 0.8436(2) 0.0253(12) Uani 1 1 d . . . . .
N1 N 0.5488(6) 0.1603(4) 0.7220(3) 0.0286(16) Uani 1 1 d . . . . .
C19 C 0.1461(7) 0.3697(4) 0.6895(4) 0.0194(19) Uani 1 1 d D . . . .
O3 O 0.8151(5) -0.0050(3) 0.6773(2) 0.0210(12) Uani 1 1 d . . . . .
N2 N 0.5989(6) -0.0034(3) 0.6439(3) 0.0229(15) Uani 1 1 d . . . . .
H2 H 0.5195 0.0223 0.6483 0.027 Uiso 1 1 calc R U . . .
N3 N -0.0615(6) 0.4056(3) 0.7546(3) 0.0193(14) Uani 1 1 d . . . . .
C20 C -0.0302(7) 0.3431(4) 0.8090(4) 0.0193(18) Uani 1 1 d D . . . .
O7 O -0.0146(5) 0.4786(3) 0.6495(2) 0.0308(13) Uani 1 1 d . . . . .
C7 C 0.5129(8) 0.2212(5) 0.6683(4) 0.0274(19) Uani 1 1 d D . . . .
C2 C 0.3004(8) 0.2528(4) 0.7350(3) 0.0185(17) Uani 1 1 d . . . . .
C8 C 0.6885(8) 0.1231(5) 0.7195(4) 0.034(2) Uani 1 1 d . . . . .
H8 H 0.7373 0.1678 0.6883 0.041 Uiso 1 1 calc R U . . .
C18 C 0.0938(8) 0.2872(4) 0.8003(3) 0.0179(17) Uani 1 1 d D . . . .
C16 C 0.1792(7) 0.3035(4) 0.7416(3) 0.0163(17) Uani 1 1 d . . . . .
O6 O -0.1032(5) 0.3363(3) 0.8612(3) 0.0267(12) Uani 1 1 d . . . . .
O1 O 0.4868(6) 0.0678(3) 0.8173(3) 0.0405(15) Uani 1 1 d . . . . .
C22 C -0.1924(7) 0.4546(4) 0.7581(4) 0.0228(18) Uani 1 1 d . . . . .
H22 H -0.1954 0.4954 0.7152 0.027 Uiso 1 1 calc R U . . .
O10 O 0.0181(5) 0.7343(3) 0.9678(2) 0.0297(13) Uani 1 1 d . . . . .
O2 O 0.5895(6) 0.2332(3) 0.6176(3) 0.0356(14) Uani 1 1 d . . . . .
C21 C 0.0197(8) 0.4226(4) 0.6944(4) 0.0216(19) Uani 1 1 d D . . . .
C25 C -0.1021(8) 0.6178(4) 0.9088(3) 0.0190(18) Uani 1 1 d . . . . .
H25 H -0.1907 0.6496 0.9058 0.023 Uiso 1 1 calc R U . . .
O5 O 0.7825(6) -0.1475(3) 0.5253(2) 0.0377(15) Uani 1 1 d . . . . .
O4 O 0.7611(6) 0.0090(3) 0.5200(2) 0.0382(15) Uani 1 1 d . . . . .
C27 C 0.0042(8) 0.6927(4) 0.9051(4) 0.0222(18) Uani 1 1 d . . . . .
C24 C -0.2053(8) 0.5186(4) 0.8218(4) 0.0210(18) Uani 1 1 d . . . . .
C15 C 0.1268(8) 0.2191(4) 0.8487(4) 0.0213(18) Uani 1 1 d . . . . .
H15 H 0.0684 0.2064 0.8874 0.026 Uiso 1 1 calc R U . . .
C4 C 0.3330(8) 0.1852(4) 0.7852(4) 0.0226(19) Uani 1 1 d D . . . .
N4 N -0.0931(6) 0.5573(3) 0.8479(3) 0.0216(14) Uani 1 1 d . . . . .
H4 H -0.0151 0.5458 0.8281 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4595(8) 0.1315(5) 0.7774(4) 0.031(2) Uani 1 1 d D . . . .
C5 C 0.3853(8) 0.2717(5) 0.6753(4) 0.0222(18) Uani 1 1 d D . . . .
C3 C 0.3491(8) 0.3349(5) 0.6256(4) 0.027(2) Uani 1 1 d . . . . .
H3 H 0.4059 0.3456 0.5859 0.032 Uiso 1 1 calc R U . . .
C10 C 0.7029(9) 0.0308(4) 0.6809(3) 0.0201(18) Uani 1 1 d . . . . .
C17 C 0.2306(8) 0.3844(4) 0.6318(4) 0.0243(19) Uani 1 1 d . . . . .
H17 H 0.2072 0.4285 0.5964 0.029 Uiso 1 1 calc R U . . .
C28 C 0.1153(9) 0.8091(4) 0.9709(4) 0.035(2) Uani 1 1 d . . . . .
H28A H 0.1176 0.8347 1.0192 0.053 Uiso 1 1 calc R U . . .
H28B H 0.0897 0.8577 0.9372 0.053 Uiso 1 1 calc R U . . .
H28C H 0.2040 0.7853 0.9584 0.053 Uiso 1 1 calc R U . . .
C9 C 0.7647(8) 0.1261(4) 0.7886(4) 0.0277(19) Uani 1 1 d . . . . .
H9A H 0.7550 0.1873 0.8102 0.041 Uiso 1 1 calc R U . . .
H9B H 0.8595 0.1137 0.7795 0.041 Uiso 1 1 calc R U . . .
H9C H 0.7290 0.0791 0.8210 0.041 Uiso 1 1 calc R U . . .
C11 C 0.6156(8) -0.0821(5) 0.5968(4) 0.029(2) Uani 1 1 d . . . . .
H11 H 0.6345 -0.1389 0.6254 0.035 Uiso 1 1 calc R U . . .
C1 C 0.2464(9) 0.1684(4) 0.8413(4) 0.028(2) Uani 1 1 d . . . . .
H1 H 0.2680 0.1221 0.8752 0.034 Uiso 1 1 calc R U . . .
C23 C -0.3098(8) 0.3871(5) 0.7498(4) 0.040(2) Uani 1 1 d . . . . .
H23A H -0.2959 0.3488 0.7074 0.061 Uiso 1 1 calc R U . . .
H23B H -0.3933 0.4219 0.7449 0.061 Uiso 1 1 calc R U . . .
H23C H -0.3151 0.3473 0.7920 0.061 Uiso 1 1 calc R U . . .
C26 C -0.1010(8) 0.5636(5) 0.9794(3) 0.0303(19) Uani 1 1 d . . . . .
H26A H -0.1731 0.5177 0.9790 0.046 Uiso 1 1 calc R U . . .
H26B H -0.1145 0.6065 1.0191 0.046 Uiso 1 1 calc R U . . .
H26C H -0.0148 0.5322 0.9849 0.046 Uiso 1 1 calc R U . . .
C14 C 0.8903(11) -0.1454(6) 0.4729(4) 0.055(3) Uani 1 1 d . . . . .
H14A H 0.9206 -0.2085 0.4632 0.083 Uiso 1 1 calc R U . . .
H14B H 0.9652 -0.1089 0.4915 0.083 Uiso 1 1 calc R U . . .
H14C H 0.8576 -0.1173 0.4288 0.083 Uiso 1 1 calc R U . . .
C13 C 0.7301(8) -0.0652(5) 0.5443(3) 0.027(2) Uani 1 1 d . . . . .
C12 C 0.4856(9) -0.0966(5) 0.5521(5) 0.050(3) Uani 1 1 d . . . . .
H12A H 0.4099 -0.1073 0.5842 0.075 Uiso 1 1 calc R U . . .
H12B H 0.4969 -0.1501 0.5208 0.075 Uiso 1 1 calc R U . . .
H12C H 0.4684 -0.0413 0.5233 0.075 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
O9 C27 1.211(9) . ?
O8 C24 1.243(8) . ?
N1 C7 1.388(9) . ?
N1 C6 1.433(10) . ?
N1 C8 1.497(10) . ?
C19 C17 1.391(10) . ?
C19 C16 1.410(9) . ?
C19 C21 1.481(10) . ?
O3 C10 1.237(9) . ?
N2 C10 1.346(9) . ?
N2 C11 1.453(8) . ?
N2 H2 0.8800 . ?
N3 C20 1.400(8) . ?
N3 C21 1.415(9) . ?
N3 C22 1.489(8) . ?
C20 O6 1.227(8) . ?
C20 C18 1.488(9) . ?
O7 C21 1.217(7) . ?
C7 O2 1.234(8) . ?
C7 C5 1.475(10) . ?
C2 C4 1.398(9) . ?
C2 C16 1.421(10) . ?
C2 C5 1.434(10) . ?
C8 C9 1.506(10) . ?
C8 C10 1.527(9) . ?
C8 H8 1.0000 . ?
C18 C15 1.381(9) . ?
C18 C16 1.416(9) . ?
O1 C6 1.218(8) . ?
C22 C24 1.519(10) . ?
C22 C23 1.535(10) . ?
C22 H22 1.0000 . ?
O10 C27 1.331(8) . ?
O10 C28 1.455(8) . ?
C25 N4 1.444(8) . ?
C25 C27 1.519(10) . ?
C25 C26 1.542(9) . ?
C25 H25 1.0000 . ?
O5 C13 1.348(8) . ?
O5 C14 1.460(10) . ?
O4 C13 1.208(8) . ?
C24 N4 1.347(9) . ?
C15 C1 1.410(10) . ?
C15 H15 0.9500 . ?
C4 C1 1.385(10) . ?
C4 C6 1.492(10) . ?
N4 H4 0.8800 . ?
C5 C3 1.356(10) . ?
C3 C17 1.388(10) . ?
C3 H3 0.9500 . ?
C17 H17 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 C13 1.530(11) . ?
C11 C12 1.561(11) . ?
C11 H11 1.0000 . ?
C1 H1 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C7 N1 C6 123.5(6) . . ?
C7 N1 C8 116.5(7) . . ?
C6 N1 C8 120.0(6) . . ?
C17 C19 C16 120.2(7) . . ?
C17 C19 C21 119.2(6) . . ?
C16 C19 C21 120.6(6) . . ?
C10 N2 C11 121.0(6) . . ?
C10 N2 H2 119.5 . . ?
C11 N2 H2 119.5 . . ?
C20 N3 C21 124.7(6) . . ?
C20 N3 C22 118.1(6) . . ?
C21 N3 C22 117.1(5) . . ?
O6 C20 N3 120.2(6) . . ?
O6 C20 C18 122.6(6) . . ?
N3 C20 C18 117.2(6) . . ?
O2 C7 N1 119.4(7) . . ?
O2 C7 C5 122.4(7) . . ?
N1 C7 C5 118.2(7) . . ?
C4 C2 C16 120.0(6) . . ?
C4 C2 C5 121.6(7) . . ?
C16 C2 C5 118.3(6) . . ?
N1 C8 C9 115.7(6) . . ?
N1 C8 C10 114.7(6) . . ?
C9 C8 C10 112.8(6) . . ?
N1 C8 H8 103.9 . . ?
C9 C8 H8 103.9 . . ?
C10 C8 H8 103.9 . . ?
C15 C18 C16 119.2(6) . . ?
C15 C18 C20 121.0(6) . . ?
C16 C18 C20 119.8(6) . . ?
C19 C16 C18 120.9(6) . . ?
C19 C16 C2 119.3(6) . . ?
C18 C16 C2 119.8(6) . . ?
N3 C22 C24 113.5(6) . . ?
N3 C22 C23 111.4(5) . . ?
C24 C22 C23 113.7(6) . . ?
N3 C22 H22 105.8 . . ?
C24 C22 H22 105.8 . . ?
C23 C22 H22 105.8 . . ?
C27 O10 C28 116.2(6) . . ?
O7 C21 N3 120.6(7) . . ?
O7 C21 C19 122.7(7) . . ?
N3 C21 C19 116.7(6) . . ?
N4 C25 C27 110.7(6) . . ?
N4 C25 C26 111.9(5) . . ?
C27 C25 C26 113.4(6) . . ?
N4 C25 H25 106.8 . . ?
C27 C25 H25 106.8 . . ?
C26 C25 H25 106.8 . . ?
C13 O5 C14 116.6(6) . . ?
O9 C27 O10 124.3(7) . . ?
O9 C27 C25 124.7(6) . . ?
O10 C27 C25 110.8(7) . . ?
O8 C24 N4 122.0(6) . . ?
O8 C24 C22 119.6(7) . . ?
N4 C24 C22 118.0(7) . . ?
C18 C15 C1 120.6(7) . . ?
C18 C15 H15 119.7 . . ?
C1 C15 H15 119.7 . . ?
C1 C4 C2 119.4(7) . . ?
C1 C4 C6 120.8(7) . . ?
C2 C4 C6 119.7(7) . . ?
C24 N4 C25 119.3(6) . . ?
C24 N4 H4 120.4 . . ?
C25 N4 H4 120.4 . . ?
O1 C6 N1 121.8(7) . . ?
O1 C6 C4 121.6(8) . . ?
N1 C6 C4 116.6(6) . . ?
C3 C5 C2 120.6(7) . . ?
C3 C5 C7 120.2(7) . . ?
C2 C5 C7 119.2(7) . . ?
C5 C3 C17 121.3(7) . . ?
C5 C3 H3 119.4 . . ?
C17 C3 H3 119.4 . . ?
O3 C10 N2 121.2(6) . . ?
O3 C10 C8 118.5(7) . . ?
N2 C10 C8 119.6(7) . . ?
C3 C17 C19 120.2(7) . . ?
C3 C17 H17 119.9 . . ?
C19 C17 H17 119.9 . . ?
O10 C28 H28A 109.5 . . ?
O10 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O10 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C11 C13 110.7(6) . . ?
N2 C11 C12 109.7(6) . . ?
C13 C11 C12 107.3(6) . . ?
N2 C11 H11 109.7 . . ?
C13 C11 H11 109.7 . . ?
C12 C11 H11 109.7 . . ?
C4 C1 C15 120.9(6) . . ?
C4 C1 H1 119.5 . . ?
C15 C1 H1 119.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O5 C14 H14A 109.5 . . ?
O5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C13 O5 125.8(7) . . ?
O4 C13 C11 125.3(7) . . ?
O5 C13 C11 108.7(6) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C21 N3 C20 O6 176.2(6) . . . . ?
C22 N3 C20 O6 -7.2(9) . . . . ?
C21 N3 C20 C18 -3.4(9) . . . . ?
C22 N3 C20 C18 173.3(5) . . . . ?
C6 N1 C7 O2 -170.6(6) . . . . ?
C8 N1 C7 O2 8.3(9) . . . . ?
C6 N1 C7 C5 11.4(9) . . . . ?
C8 N1 C7 C5 -169.7(6) . . . . ?
C7 N1 C8 C9 132.8(6) . . . . ?
C6 N1 C8 C9 -48.3(9) . . . . ?
C7 N1 C8 C10 -93.3(7) . . . . ?
C6 N1 C8 C10 85.7(8) . . . . ?
O6 C20 C18 C15 5.3(10) . . . . ?
N3 C20 C18 C15 -175.2(6) . . . . ?
O6 C20 C18 C16 -175.0(6) . . . . ?
N3 C20 C18 C16 4.5(9) . . . . ?
C17 C19 C16 C18 -179.5(6) . . . . ?
C21 C19 C16 C18 -1.1(9) . . . . ?
C17 C19 C16 C2 0.8(9) . . . . ?
C21 C19 C16 C2 179.2(6) . . . . ?
C15 C18 C16 C19 177.4(6) . . . . ?
C20 C18 C16 C19 -2.4(9) . . . . ?
C15 C18 C16 C2 -2.9(9) . . . . ?
C20 C18 C16 C2 177.4(6) . . . . ?
C4 C2 C16 C19 -178.3(6) . . . . ?
C5 C2 C16 C19 0.3(8) . . . . ?
C4 C2 C16 C18 2.0(9) . . . . ?
C5 C2 C16 C18 -179.4(6) . . . . ?
C20 N3 C22 C24 64.4(7) . . . . ?
C21 N3 C22 C24 -118.7(6) . . . . ?
C20 N3 C22 C23 -65.6(7) . . . . ?
C21 N3 C22 C23 111.4(6) . . . . ?
C20 N3 C21 O7 -179.7(6) . . . . ?
C22 N3 C21 O7 3.6(8) . . . . ?
C20 N3 C21 C19 0.0(9) . . . . ?
C22 N3 C21 C19 -176.7(5) . . . . ?
C17 C19 C21 O7 0.5(9) . . . . ?
C16 C19 C21 O7 -177.9(6) . . . . ?
C17 C19 C21 N3 -179.2(5) . . . . ?
C16 C19 C21 N3 2.3(9) . . . . ?
C28 O10 C27 O9 -3.1(10) . . . . ?
C28 O10 C27 C25 -178.7(6) . . . . ?
N4 C25 C27 O9 19.4(9) . . . . ?
C26 C25 C27 O9 146.2(7) . . . . ?
N4 C25 C27 O10 -165.0(5) . . . . ?
C26 C25 C27 O10 -38.2(8) . . . . ?
N3 C22 C24 O8 -157.6(6) . . . . ?
C23 C22 C24 O8 -28.8(9) . . . . ?
N3 C22 C24 N4 29.3(8) . . . . ?
C23 C22 C24 N4 158.0(6) . . . . ?
C16 C18 C15 C1 2.2(10) . . . . ?
C20 C18 C15 C1 -178.1(6) . . . . ?
C16 C2 C4 C1 -0.2(9) . . . . ?
C5 C2 C4 C1 -178.8(6) . . . . ?
C16 C2 C4 C6 179.2(6) . . . . ?
C5 C2 C4 C6 0.6(9) . . . . ?
O8 C24 N4 C25 7.6(9) . . . . ?
C22 C24 N4 C25 -179.4(5) . . . . ?
C27 C25 N4 C24 -147.7(6) . . . . ?
C26 C25 N4 C24 84.7(8) . . . . ?
C7 N1 C6 O1 168.6(6) . . . . ?
C8 N1 C6 O1 -10.3(10) . . . . ?
C7 N1 C6 C4 -13.2(9) . . . . ?
C8 N1 C6 C4 167.9(6) . . . . ?
C1 C4 C6 O1 4.4(10) . . . . ?
C2 C4 C6 O1 -174.9(6) . . . . ?
C1 C4 C6 N1 -173.8(6) . . . . ?
C2 C4 C6 N1 6.9(9) . . . . ?
C4 C2 C5 C3 177.3(6) . . . . ?
C16 C2 C5 C3 -1.3(9) . . . . ?
C4 C2 C5 C7 -2.6(9) . . . . ?
C16 C2 C5 C7 178.7(6) . . . . ?
O2 C7 C5 C3 -1.0(10) . . . . ?
N1 C7 C5 C3 177.0(6) . . . . ?
O2 C7 C5 C2 179.0(6) . . . . ?
N1 C7 C5 C2 -3.1(9) . . . . ?
C2 C5 C3 C17 1.2(10) . . . . ?
C7 C5 C3 C17 -178.9(6) . . . . ?
C11 N2 C10 O3 -1.8(10) . . . . ?
C11 N2 C10 C8 169.3(6) . . . . ?
N1 C8 C10 O3 -179.1(6) . . . . ?
C9 C8 C10 O3 -43.8(9) . . . . ?
N1 C8 C10 N2 9.6(10) . . . . ?
C9 C8 C10 N2 144.9(7) . . . . ?
C5 C3 C17 C19 -0.1(10) . . . . ?
C16 C19 C17 C3 -0.9(9) . . . . ?
C21 C19 C17 C3 -179.3(6) . . . . ?
C10 N2 C11 C13 -52.7(8) . . . . ?
C10 N2 C11 C12 -170.9(6) . . . . ?
C2 C4 C1 C15 -0.6(10) . . . . ?
C6 C4 C1 C15 -180.0(6) . . . . ?
C18 C15 C1 C4 -0.4(10) . . . . ?
C14 O5 C13 O4 2.9(11) . . . . ?
C14 O5 C13 C11 177.6(6) . . . . ?
N2 C11 C13 O4 -32.9(10) . . . . ?
C12 C11 C13 O4 86.8(8) . . . . ?
N2 C11 C13 O5 152.4(6) . . . . ?
C12 C11 C13 O5 -87.9(7) . . . . ?

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
