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

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

data_cu_60121a
_database_code_depnum_ccdc_archive 'CCDC 1484143'
_audit_update_record             
;
2016-06-08 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H36 N2 O6'
_chemical_formula_weight         532.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.9835(14)
_cell_length_b                   12.2707(16)
_cell_length_c                   23.460(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2873.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2811
_cell_measurement_theta_min      3.77
_cell_measurement_theta_max      67.24

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.693
_shelx_estimated_absorpt_T_min   0.846
_shelx_estimated_absorpt_T_max   0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.589
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14287
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.768
_diffrn_reflns_theta_max         67.416
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 0.918
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_point_group_measured_fraction_full 0.872
_reflns_number_total             4523
_reflns_number_gt                3799
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_max     0.815
_reflns_Friedel_fraction_full    0.812

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.2000P)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     SHELXL
_refine_ls_extinction_coef       0.109(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1391 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.11(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4523
_refine_ls_number_parameters     360
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.1975
_refine_ls_R_factor_gt           0.1890
_refine_ls_wR_factor_ref         0.4010
_refine_ls_wR_factor_gt          0.3905
_refine_ls_goodness_of_fit_ref   1.778
_refine_ls_restrained_S_all      1.797
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1124(7) 0.3560(6) 0.1530(3) 0.0231(16) Uani 1 1 d . . . . .
N2 N 0.3639(8) 0.0691(6) 0.2268(3) 0.032(2) Uani 1 1 d . . . . .
O1 O 0.3430(7) 0.3615(6) 0.1341(3) 0.0410(19) Uani 1 1 d . . . . .
O2 O 0.1649(7) 0.5112(5) 0.1071(3) 0.0387(18) Uani 1 1 d . . . . .
O3 O -0.0547(8) 0.4789(8) 0.1285(5) 0.066(3) Uani 1 1 d . . . . .
O4 O 0.1396(7) 0.1642(6) 0.0658(3) 0.0356(17) Uani 1 1 d . . . . .
O5 O 0.182(2) -0.0119(9) 0.0750(9) 0.153(9) Uani 1 1 d . U . . .
O6 O 0.5786(15) 0.0947(16) 0.1199(11) 0.150(8) Uani 1 1 d . . . . .
C1 C 0.2427(8) 0.3141(6) 0.1522(3) 0.0213(17) Uani 1 1 d . . . . .
C2 C 0.2424(8) 0.1997(6) 0.1772(3) 0.0207(18) Uani 1 1 d . . . . .
C3 C 0.0976(8) 0.1859(6) 0.1942(3) 0.0207(17) Uani 1 1 d . . . . .
C4 C 0.0344(10) 0.1005(9) 0.2213(4) 0.037(2) Uani 1 1 d . . . . .
H4 H 0.0819 0.0382 0.2314 0.045 Uiso 1 1 calc R U . . .
C5 C -0.1036(13) 0.1093(10) 0.2336(5) 0.048(3) Uani 1 1 d . . . . .
H5 H -0.1471 0.0527 0.2523 0.057 Uiso 1 1 calc R U . . .
C6 C -0.1753(12) 0.2017(11) 0.2179(6) 0.054(3) Uani 1 1 d . . . . .
H6 H -0.2664 0.2053 0.2259 0.064 Uiso 1 1 calc R U . . .
C7 C -0.1135(10) 0.2892(9) 0.1902(5) 0.041(2) Uani 1 1 d . . . . .
H7 H -0.1610 0.3513 0.1798 0.050 Uiso 1 1 calc R U . . .
C8 C 0.0240(8) 0.2787(7) 0.1789(3) 0.0233(19) Uani 1 1 d . . . . .
C9 C 0.0646(10) 0.4531(8) 0.1297(4) 0.030(2) Uani 1 1 d . . . . .
C10 C 0.1404(12) 0.6171(7) 0.0792(4) 0.037(2) Uani 1 1 d . . . . .
C11 C 0.2803(15) 0.6532(11) 0.0631(7) 0.061(3) Uani 1 1 d . . . . .
H11A H 0.3328 0.6632 0.0970 0.092 Uiso 1 1 calc R U . . .
H11B H 0.2756 0.7208 0.0425 0.092 Uiso 1 1 calc R U . . .
H11C H 0.3213 0.5987 0.0395 0.092 Uiso 1 1 calc R U . . .
C12 C 0.056(2) 0.6007(15) 0.0269(7) 0.083(6) Uani 1 1 d . . . . .
H12A H 0.0995 0.5503 0.0017 0.124 Uiso 1 1 calc R U . . .
H12B H 0.0439 0.6692 0.0078 0.124 Uiso 1 1 calc R U . . .
H12C H -0.0300 0.5721 0.0377 0.124 Uiso 1 1 calc R U . . .
C13 C 0.0795(18) 0.6991(9) 0.1209(7) 0.067(4) Uani 1 1 d . . . . .
H13A H -0.0058 0.6728 0.1339 0.100 Uiso 1 1 calc R U . . .
H13B H 0.0677 0.7679 0.1021 0.100 Uiso 1 1 calc R U . . .
H13C H 0.1383 0.7082 0.1530 0.100 Uiso 1 1 calc R U . . .
C14 C 0.2975(9) 0.1167(7) 0.1335(3) 0.0266(19) Uani 1 1 d . . . . .
H14 H 0.3664 0.1568 0.1124 0.032 Uiso 1 1 calc R U . . .
C15 C 0.3750(15) 0.0306(9) 0.1673(5) 0.050(3) Uani 1 1 d . . . . .
C16 C 0.4622(11) 0.0346(10) 0.2699(5) 0.046(3) Uani 1 1 d . . . . .
H16A H 0.5444 0.0761 0.2658 0.055 Uiso 1 1 calc R U . . .
H16B H 0.4830 -0.0421 0.2653 0.055 Uiso 1 1 calc R U . . .
C17 C 0.4017(14) 0.0544(10) 0.3268(5) 0.051(3) Uani 1 1 d . . . . .
H17A H 0.4704 0.0455 0.3557 0.062 Uiso 1 1 calc R U . . .
H17B H 0.3334 -0.0003 0.3336 0.062 Uiso 1 1 calc R U . . .
C18 C 0.3408(11) 0.1641(9) 0.3331(4) 0.038(3) Uani 1 1 d . . . . .
C19 C 0.3099(15) 0.2054(12) 0.3866(5) 0.058(3) Uani 1 1 d . . . . .
H19 H 0.3318 0.1651 0.4188 0.070 Uiso 1 1 calc R U . . .
C20 C 0.2458(16) 0.3075(14) 0.3932(5) 0.067(4) Uani 1 1 d . . . . .
H20 H 0.2270 0.3344 0.4294 0.080 Uiso 1 1 calc R U . . .
C21 C 0.2118(14) 0.3665(11) 0.3455(4) 0.051(3) Uani 1 1 d . . . . .
H21 H 0.1670 0.4325 0.3493 0.062 Uiso 1 1 calc R U . . .
C22 C 0.2445(12) 0.3276(8) 0.2913(4) 0.037(2) Uani 1 1 d . . . . .
H22 H 0.2241 0.3698 0.2595 0.045 Uiso 1 1 calc R U . . .
C23 C 0.3069(10) 0.2271(8) 0.2838(4) 0.030(2) Uani 1 1 d . . . . .
C24 C 0.3438(9) 0.1865(7) 0.2257(4) 0.0247(19) Uani 1 1 d . . . . .
H24 H 0.4280 0.2212 0.2142 0.030 Uiso 1 1 calc R U . . .
C25 C 0.2012(13) 0.0792(9) 0.0889(5) 0.046(3) Uani 1 1 d . . . . .
C26 C 0.0399(11) 0.1554(10) 0.0194(4) 0.041(3) Uani 1 1 d . U . . .
C27 C -0.005(2) 0.2697(15) 0.0115(8) 0.096(7) Uani 1 1 d . U . . .
H27A H 0.0700 0.3180 0.0155 0.145 Uiso 1 1 calc R U . . .
H27B H -0.0715 0.2872 0.0397 0.145 Uiso 1 1 calc R U . . .
H27C H -0.0430 0.2780 -0.0259 0.145 Uiso 1 1 calc R U . . .
C28 C 0.100(2) 0.108(3) -0.0314(6) 0.141(10) Uani 1 1 d . U . . .
H28A H 0.1304 0.0357 -0.0231 0.212 Uiso 1 1 calc R U . . .
H28B H 0.1751 0.1522 -0.0430 0.212 Uiso 1 1 calc R U . . .
H28C H 0.0352 0.1061 -0.0615 0.212 Uiso 1 1 calc R U . . .
C29 C -0.083(2) 0.0938(18) 0.0414(9) 0.101(7) Uani 1 1 d . U . . .
H29A H -0.1563 0.1044 0.0157 0.152 Uiso 1 1 calc R U . . .
H29B H -0.1065 0.1208 0.0785 0.152 Uiso 1 1 calc R U . . .
H29C H -0.0623 0.0175 0.0439 0.152 Uiso 1 1 calc R U . . .
C30 C 0.522(2) 0.032(2) 0.1497(8) 0.099(7) Uani 1 1 d . U . . .
H30 H 0.5746 -0.0238 0.1646 0.119 Uiso 1 1 calc R U . . .
C31 C 0.335(3) -0.0881(10) 0.1629(9) 0.119(10) Uani 1 1 d . U . . .
H31A H 0.4091 -0.1333 0.1736 0.178 Uiso 1 1 calc R U . . .
H31B H 0.3093 -0.1043 0.1243 0.178 Uiso 1 1 calc R U . . .
H31C H 0.2606 -0.1020 0.1879 0.178 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
N1 C9 1.396(11) . ?
N1 C1 1.399(11) . ?
N1 C8 1.432(10) . ?
N2 C24 1.455(10) . ?
N2 C16 1.470(10) . ?
N2 C15 1.479(13) . ?
O1 C1 1.233(10) . ?
O2 C9 1.338(12) . ?
O2 C10 1.475(10) . ?
O3 C9 1.232(13) . ?
O4 C25 1.328(13) . ?
O4 C26 1.478(9) . ?
O5 C25 1.180(14) . ?
O6 C30 1.18(2) . ?
C1 C2 1.522(10) . ?
C2 C3 1.508(12) . ?
C2 C24 1.532(9) . ?
C2 C14 1.546(11) . ?
C3 C4 1.379(12) . ?
C3 C8 1.401(11) . ?
C4 C5 1.412(17) . ?
C5 C6 1.390(19) . ?
C6 C7 1.398(14) . ?
C7 C8 1.404(13) . ?
C10 C12 1.505(16) . ?
C10 C11 1.514(17) . ?
C10 C13 1.530(14) . ?
C14 C25 1.493(12) . ?
C14 C15 1.530(13) . ?
C15 C31 1.515(17) . ?
C15 C30 1.53(3) . ?
C16 C17 1.485(18) . ?
C17 C18 1.485(16) . ?
C18 C19 1.389(16) . ?
C18 C23 1.430(12) . ?
C19 C20 1.41(2) . ?
C20 C21 1.377(18) . ?
C21 C22 1.396(14) . ?
C22 C23 1.394(14) . ?
C23 C24 1.498(13) . ?
C26 C28 1.455(19) . ?
C26 C27 1.48(2) . ?
C26 C29 1.53(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C1 128.8(7) . . ?
C9 N1 C8 121.5(7) . . ?
C1 N1 C8 109.6(7) . . ?
C24 N2 C16 113.0(8) . . ?
C24 N2 C15 108.0(7) . . ?
C16 N2 C15 120.5(9) . . ?
C9 O2 C10 121.3(8) . . ?
C25 O4 C26 123.7(8) . . ?
O1 C1 N1 125.9(7) . . ?
O1 C1 C2 124.7(8) . . ?
N1 C1 C2 109.4(6) . . ?
C3 C2 C1 102.0(6) . . ?
C3 C2 C24 115.2(7) . . ?
C1 C2 C24 112.5(6) . . ?
C3 C2 C14 116.2(7) . . ?
C1 C2 C14 110.6(7) . . ?
C24 C2 C14 100.8(6) . . ?
C4 C3 C8 119.6(8) . . ?
C4 C3 C2 130.2(8) . . ?
C8 C3 C2 110.1(7) . . ?
C3 C4 C5 118.9(10) . . ?
C6 C5 C4 120.7(10) . . ?
C5 C6 C7 121.4(11) . . ?
C6 C7 C8 116.6(10) . . ?
C3 C8 C7 122.7(8) . . ?
C3 C8 N1 108.9(7) . . ?
C7 C8 N1 128.4(8) . . ?
O3 C9 O2 125.3(9) . . ?
O3 C9 N1 124.0(9) . . ?
O2 C9 N1 110.7(7) . . ?
O2 C10 C12 109.7(10) . . ?
O2 C10 C11 102.5(9) . . ?
C12 C10 C11 110.6(12) . . ?
O2 C10 C13 111.2(9) . . ?
C12 C10 C13 112.8(13) . . ?
C11 C10 C13 109.5(11) . . ?
C25 C14 C15 118.4(9) . . ?
C25 C14 C2 116.0(8) . . ?
C15 C14 C2 107.0(7) . . ?
N2 C15 C31 110.6(12) . . ?
N2 C15 C30 108.8(12) . . ?
C31 C15 C30 104.4(16) . . ?
N2 C15 C14 103.4(8) . . ?
C31 C15 C14 119.6(12) . . ?
C30 C15 C14 109.9(12) . . ?
N2 C16 C17 107.4(9) . . ?
C16 C17 C18 113.8(9) . . ?
C19 C18 C23 118.7(11) . . ?
C19 C18 C17 120.8(10) . . ?
C23 C18 C17 120.4(9) . . ?
C18 C19 C20 121.6(11) . . ?
C21 C20 C19 119.1(12) . . ?
C20 C21 C22 120.3(13) . . ?
C23 C22 C21 121.4(10) . . ?
C22 C23 C18 118.9(9) . . ?
C22 C23 C24 121.2(8) . . ?
C18 C23 C24 119.9(9) . . ?
N2 C24 C23 110.2(7) . . ?
N2 C24 C2 102.1(6) . . ?
C23 C24 C2 118.6(7) . . ?
O5 C25 O4 123.9(10) . . ?
O5 C25 C14 126.1(11) . . ?
O4 C25 C14 110.0(8) . . ?
C28 C26 O4 110.6(10) . . ?
C28 C26 C27 113.4(17) . . ?
O4 C26 C27 103.1(9) . . ?
C28 C26 C29 114.3(17) . . ?
O4 C26 C29 109.1(10) . . ?
C27 C26 C29 105.5(15) . . ?
O6 C30 C15 128.8(16) . . ?

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
C9 N1 C1 O1 6.4(14) . . . . ?
C8 N1 C1 O1 -178.0(9) . . . . ?
C9 N1 C1 C2 -173.5(8) . . . . ?
C8 N1 C1 C2 2.1(9) . . . . ?
O1 C1 C2 C3 177.7(8) . . . . ?
N1 C1 C2 C3 -2.4(8) . . . . ?
O1 C1 C2 C24 53.8(11) . . . . ?
N1 C1 C2 C24 -126.3(7) . . . . ?
O1 C1 C2 C14 -58.1(11) . . . . ?
N1 C1 C2 C14 121.8(7) . . . . ?
C1 C2 C3 C4 -177.2(8) . . . . ?
C24 C2 C3 C4 -55.1(12) . . . . ?
C14 C2 C3 C4 62.4(11) . . . . ?
C1 C2 C3 C8 1.9(8) . . . . ?
C24 C2 C3 C8 124.1(7) . . . . ?
C14 C2 C3 C8 -118.4(8) . . . . ?
C8 C3 C4 C5 -0.5(14) . . . . ?
C2 C3 C4 C5 178.6(9) . . . . ?
C3 C4 C5 C6 0.9(17) . . . . ?
C4 C5 C6 C7 -0.8(19) . . . . ?
C5 C6 C7 C8 0.4(17) . . . . ?
C4 C3 C8 C7 0.1(14) . . . . ?
C2 C3 C8 C7 -179.2(9) . . . . ?
C4 C3 C8 N1 178.4(8) . . . . ?
C2 C3 C8 N1 -0.8(9) . . . . ?
C6 C7 C8 C3 0.0(15) . . . . ?
C6 C7 C8 N1 -178.0(10) . . . . ?
C9 N1 C8 C3 175.1(8) . . . . ?
C1 N1 C8 C3 -0.8(9) . . . . ?
C9 N1 C8 C7 -6.6(14) . . . . ?
C1 N1 C8 C7 177.4(9) . . . . ?
C10 O2 C9 O3 1.9(16) . . . . ?
C10 O2 C9 N1 179.5(8) . . . . ?
C1 N1 C9 O3 173.7(11) . . . . ?
C8 N1 C9 O3 -1.4(16) . . . . ?
C1 N1 C9 O2 -3.9(13) . . . . ?
C8 N1 C9 O2 -179.0(7) . . . . ?
C9 O2 C10 C12 -64.7(14) . . . . ?
C9 O2 C10 C11 177.7(10) . . . . ?
C9 O2 C10 C13 60.8(14) . . . . ?
C3 C2 C14 C25 35.1(11) . . . . ?
C1 C2 C14 C25 -80.5(10) . . . . ?
C24 C2 C14 C25 160.3(8) . . . . ?
C3 C2 C14 C15 -99.5(10) . . . . ?
C1 C2 C14 C15 144.9(9) . . . . ?
C24 C2 C14 C15 25.7(10) . . . . ?
C24 N2 C15 C31 -154.9(13) . . . . ?
C16 N2 C15 C31 73.3(17) . . . . ?
C24 N2 C15 C30 91.1(12) . . . . ?
C16 N2 C15 C30 -40.8(15) . . . . ?
C24 N2 C15 C14 -25.6(12) . . . . ?
C16 N2 C15 C14 -157.5(9) . . . . ?
C25 C14 C15 N2 -134.8(10) . . . . ?
C2 C14 C15 N2 -1.4(12) . . . . ?
C25 C14 C15 C31 -11.3(19) . . . . ?
C2 C14 C15 C31 122.0(15) . . . . ?
C25 C14 C15 C30 109.3(15) . . . . ?
C2 C14 C15 C30 -117.4(13) . . . . ?
C24 N2 C16 C17 68.8(11) . . . . ?
C15 N2 C16 C17 -161.6(10) . . . . ?
N2 C16 C17 C18 -47.7(13) . . . . ?
C16 C17 C18 C19 -164.1(11) . . . . ?
C16 C17 C18 C23 18.9(15) . . . . ?
C23 C18 C19 C20 0.2(19) . . . . ?
C17 C18 C19 C20 -176.9(12) . . . . ?
C18 C19 C20 C21 1(2) . . . . ?
C19 C20 C21 C22 -2(2) . . . . ?
C20 C21 C22 C23 2.6(19) . . . . ?
C21 C22 C23 C18 -1.5(16) . . . . ?
C21 C22 C23 C24 -179.0(10) . . . . ?
C19 C18 C23 C22 0.1(16) . . . . ?
C17 C18 C23 C22 177.2(10) . . . . ?
C19 C18 C23 C24 177.7(10) . . . . ?
C17 C18 C23 C24 -5.3(15) . . . . ?
C16 N2 C24 C23 -54.5(11) . . . . ?
C15 N2 C24 C23 169.7(9) . . . . ?
C16 N2 C24 C2 178.5(8) . . . . ?
C15 N2 C24 C2 42.7(10) . . . . ?
C22 C23 C24 N2 -160.6(9) . . . . ?
C18 C23 C24 N2 21.9(12) . . . . ?
C22 C23 C24 C2 -43.5(12) . . . . ?
C18 C23 C24 C2 139.0(9) . . . . ?
C3 C2 C24 N2 85.3(8) . . . . ?
C1 C2 C24 N2 -158.4(7) . . . . ?
C14 C2 C24 N2 -40.6(8) . . . . ?
C3 C2 C24 C23 -36.1(10) . . . . ?
C1 C2 C24 C23 80.2(9) . . . . ?
C14 C2 C24 C23 -162.0(8) . . . . ?
C26 O4 C25 O5 0(2) . . . . ?
C26 O4 C25 C14 178.8(9) . . . . ?
C15 C14 C25 O5 -3(2) . . . . ?
C2 C14 C25 O5 -133(2) . . . . ?
C15 C14 C25 O4 177.5(10) . . . . ?
C2 C14 C25 O4 48.2(13) . . . . ?
C25 O4 C26 C28 -62(2) . . . . ?
C25 O4 C26 C27 176.4(14) . . . . ?
C25 O4 C26 C29 64.6(16) . . . . ?
N2 C15 C30 O6 -105(3) . . . . ?
C31 C15 C30 O6 137(3) . . . . ?
C14 C15 C30 O6 8(3) . . . . ?

_refine_diff_density_max         1.483
_refine_diff_density_min         -0.831
_refine_diff_density_rms         0.302

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_cu_60113b
_database_code_depnum_ccdc_archive 'CCDC 1484144'
_audit_update_record             
;
2016-06-08 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H44 N2 O7'
_chemical_formula_weight         652.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   22.0361(10)
_cell_length_b                   8.9726(4)
_cell_length_c                   18.4215(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.967(3)
_cell_angle_gamma                90
_cell_volume                     3597.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2438
_cell_measurement_theta_min      4.06
_cell_measurement_theta_max      69.45

_exptl_crystal_description       sheet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.640
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.668
_shelx_estimated_absorpt_T_min   0.674
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.561
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9159
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.428
_diffrn_reflns_theta_max         69.495
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measured_fraction_theta_full 0.936
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_Laue_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.729
_diffrn_reflns_point_group_measured_fraction_full 0.739
_reflns_number_total             4929
_reflns_number_gt                4239
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.470
_reflns_Friedel_fraction_max     0.500
_reflns_Friedel_fraction_full    0.512

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.2000P)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     SHELXL
_refine_ls_extinction_coef       0.0013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1235 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.1(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4929
_refine_ls_number_parameters     442
_refine_ls_number_restraints     67
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0977
_refine_ls_wR_factor_ref         0.3097
_refine_ls_wR_factor_gt          0.2925
_refine_ls_goodness_of_fit_ref   1.334
_refine_ls_restrained_S_all      1.363
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5782(3) 0.4889(8) 0.7000(3) 0.0694(18) Uani 1 1 d . . . . .
N2 N 0.7525(2) 0.3193(7) 0.8384(3) 0.0568(13) Uani 1 1 d . . . . .
O1 O 0.5508(2) 0.3156(7) 0.7823(3) 0.0732(15) Uani 1 1 d . . . . .
O2 O 0.5096(8) 0.6032(10) 0.6133(7) 0.206(8) Uani 1 1 d D . . . .
O3 O 0.4849(3) 0.3713(10) 0.6586(5) 0.107(3) Uani 1 1 d D U . . .
O4 O 0.57602(19) 0.6511(5) 0.8538(3) 0.0529(10) Uani 1 1 d . . . . .
O5 O 0.6592(3) 0.7112(6) 0.9348(4) 0.0864(19) Uani 1 1 d . . . . .
O6 O 0.6910(4) 0.0834(9) 0.5066(3) 0.094(2) Uani 1 1 d . . . . .
O7 O 0.5944(3) 0.0476(7) 0.5682(3) 0.0747(15) Uani 1 1 d . . . . .
C1 C 0.5865(3) 0.4008(8) 0.7636(3) 0.0533(15) Uani 1 1 d . . . . .
C2 C 0.6515(2) 0.4311(6) 0.8045(3) 0.0420(11) Uani 1 1 d . . . . .
C3 C 0.6737(3) 0.5594(7) 0.7625(4) 0.0531(14) Uani 1 1 d . . . . .
C4 C 0.7265(4) 0.6436(9) 0.7805(6) 0.082(2) Uani 1 1 d D . . . .
H4 H 0.7540 0.6266 0.8233 0.098 Uiso 1 1 calc R U . . .
C5 C 0.7364(7) 0.7570(13) 0.7302(10) 0.128(5) Uani 1 1 d D U . . .
H5 H 0.7709 0.8180 0.7392 0.153 Uiso 1 1 calc R U . . .
C6 C 0.6925(8) 0.7756(13) 0.6657(8) 0.131(6) Uani 1 1 d D U . . .
H6 H 0.7000 0.8485 0.6323 0.157 Uiso 1 1 calc R U . . .
C7 C 0.6387(7) 0.6916(14) 0.6490(5) 0.110(4) Uani 1 1 d D U . . .
H7 H 0.6110 0.7069 0.6062 0.132 Uiso 1 1 calc R U . . .
C8 C 0.6291(5) 0.5839(10) 0.7003(4) 0.080(3) Uani 1 1 d . U . . .
C9 C 0.5138(6) 0.4924(10) 0.6508(5) 0.108(4) Uani 1 1 d D U . . .
C10 C 0.4183(6) 0.3625(15) 0.6315(8) 0.118(4) Uani 1 1 d D U . . .
C11 C 0.4015(7) 0.210(3) 0.6585(17) 0.186(11) Uani 1 1 d . . . . .
H11A H 0.4084 0.2089 0.7112 0.279 Uiso 1 1 calc R U . . .
H11B H 0.4264 0.1354 0.6404 0.279 Uiso 1 1 calc R U . . .
H11C H 0.3589 0.1901 0.6408 0.279 Uiso 1 1 calc R U . . .
C12 C 0.3885(7) 0.480(2) 0.6647(13) 0.151(7) Uani 1 1 d . U . . .
H12A H 0.3480 0.4485 0.6707 0.226 Uiso 1 1 calc R U . . .
H12B H 0.3859 0.5665 0.6339 0.226 Uiso 1 1 calc R U . . .
H12C H 0.4117 0.5030 0.7119 0.226 Uiso 1 1 calc R U . . .
C13 C 0.4091(10) 0.380(3) 0.5486(9) 0.190(10) Uani 1 1 d D U . . .
H13A H 0.3689 0.3457 0.5280 0.285 Uiso 1 1 calc R U . . .
H13B H 0.4396 0.3230 0.5289 0.285 Uiso 1 1 calc R U . . .
H13C H 0.4132 0.4835 0.5365 0.285 Uiso 1 1 calc R U . . .
C14 C 0.6477(2) 0.4595(6) 0.8862(3) 0.0431(11) Uani 1 1 d . . . . .
H14 H 0.6144 0.3973 0.8990 0.052 Uiso 1 1 calc R U . . .
C15 C 0.7059(3) 0.4169(7) 0.9377(3) 0.0507(13) Uani 1 1 d . . . . .
C16 C 0.7532(3) 0.3562(7) 0.9114(4) 0.0543(14) Uani 1 1 d . . . . .
H16 H 0.7889 0.3375 0.9442 0.065 Uiso 1 1 calc R U . . .
C17 C 0.8056(3) 0.2651(11) 0.8115(5) 0.075(2) Uani 1 1 d . . . . .
H17A H 0.8063 0.1570 0.8133 0.090 Uiso 1 1 calc R U . . .
H17B H 0.8424 0.3018 0.8421 0.090 Uiso 1 1 calc R U . . .
C18 C 0.8045(3) 0.3172(11) 0.7328(5) 0.076(2) Uani 1 1 d . . . . .
H18A H 0.8403 0.2802 0.7138 0.091 Uiso 1 1 calc R U . . .
H18B H 0.8048 0.4252 0.7307 0.091 Uiso 1 1 calc R U . . .
C19 C 0.7457(3) 0.2560(8) 0.6871(4) 0.0600(15) Uani 1 1 d . . . . .
C20 C 0.7456(4) 0.2081(10) 0.6157(4) 0.0684(19) Uani 1 1 d . . . . .
H20 H 0.7806 0.2205 0.5940 0.082 Uiso 1 1 calc R U . . .
C21 C 0.6936(4) 0.1413(9) 0.5757(4) 0.0679(19) Uani 1 1 d . . . . .
C22 C 0.6421(4) 0.1226(8) 0.6094(4) 0.0590(15) Uani 1 1 d . . . . .
C23 C 0.6422(3) 0.1680(7) 0.6798(4) 0.0536(14) Uani 1 1 d . . . . .
H23 H 0.6076 0.1520 0.7018 0.064 Uiso 1 1 calc R U . . .
C24 C 0.6942(3) 0.2391(7) 0.7204(4) 0.0516(13) Uani 1 1 d . . . . .
C25 C 0.6919(3) 0.2872(6) 0.7979(3) 0.0470(12) Uani 1 1 d . . . . .
H25 H 0.6742 0.2052 0.8230 0.056 Uiso 1 1 calc R U . . .
C26 C 0.6297(3) 0.6224(7) 0.8960(3) 0.0483(12) Uani 1 1 d . . . . .
C27 C 0.5488(3) 0.8034(8) 0.8497(4) 0.0582(15) Uani 1 1 d . . . . .
C28 C 0.4916(5) 0.7791(14) 0.7917(8) 0.109(4) Uani 1 1 d . . . . .
H28A H 0.5038 0.7433 0.7471 0.164 Uiso 1 1 calc R U . . .
H28B H 0.4699 0.8717 0.7824 0.164 Uiso 1 1 calc R U . . .
H28C H 0.4652 0.7072 0.8095 0.164 Uiso 1 1 calc R U . . .
C29 C 0.5297(7) 0.8387(14) 0.9226(6) 0.112(4) Uani 1 1 d . U . . .
H29A H 0.5060 0.7575 0.9373 0.167 Uiso 1 1 calc R U . . .
H29B H 0.5054 0.9279 0.9183 0.167 Uiso 1 1 calc R U . . .
H29C H 0.5656 0.8533 0.9587 0.167 Uiso 1 1 calc R U . . .
C30 C 0.5923(5) 0.9128(10) 0.8243(6) 0.085(2) Uani 1 1 d . . . . .
H30A H 0.6277 0.9239 0.8615 0.127 Uiso 1 1 calc R U . . .
H30B H 0.5721 1.0074 0.8154 0.127 Uiso 1 1 calc R U . . .
H30C H 0.6048 0.8774 0.7798 0.127 Uiso 1 1 calc R U . . .
C31 C 0.7083(3) 0.4429(8) 1.0194(4) 0.0615(16) Uani 1 1 d . . . . .
H31A H 0.7078 0.5492 1.0287 0.074 Uiso 1 1 calc R U . . .
H31B H 0.7465 0.4031 1.0455 0.074 Uiso 1 1 calc R U . . .
C32 C 0.6547(3) 0.3701(8) 1.0484(3) 0.0577(15) Uani 1 1 d . . . . .
C33 C 0.6496(4) 0.2171(10) 1.0523(6) 0.081(2) Uani 1 1 d . . . . .
H33 H 0.6777 0.1566 1.0334 0.097 Uiso 1 1 calc R U . . .
C34 C 0.6040(6) 0.1542(13) 1.0836(9) 0.110(4) Uani 1 1 d . . . . .
H34 H 0.6039 0.0515 1.0904 0.132 Uiso 1 1 calc R U . . .
C35 C 0.5577(6) 0.2383(16) 1.1056(7) 0.102(3) Uani 1 1 d . . . . .
H35 H 0.5264 0.1926 1.1258 0.122 Uiso 1 1 calc R U . . .
C36 C 0.5586(5) 0.3875(14) 1.0974(7) 0.097(3) Uani 1 1 d . . . . .
H36 H 0.5266 0.4456 1.1093 0.116 Uiso 1 1 calc R U . . .
C37 C 0.6080(4) 0.4533(10) 1.0711(5) 0.077(2) Uani 1 1 d . . . . .
H37 H 0.6098 0.5567 1.0685 0.093 Uiso 1 1 calc R U . . .
C38 C 0.7429(6) 0.1003(17) 0.4704(5) 0.107(4) Uani 1 1 d . . . . .
H38A H 0.7576 0.2011 0.4760 0.161 Uiso 1 1 calc R U . . .
H38B H 0.7316 0.0780 0.4192 0.161 Uiso 1 1 calc R U . . .
H38C H 0.7748 0.0334 0.4917 0.161 Uiso 1 1 calc R U . . .
C39 C 0.5427(4) 0.0208(13) 0.5998(5) 0.081(2) Uani 1 1 d . . . . .
H39A H 0.5530 -0.0442 0.6413 0.122 Uiso 1 1 calc R U . . .
H39B H 0.5118 -0.0252 0.5644 0.122 Uiso 1 1 calc R U . . .
H39C H 0.5273 0.1134 0.6158 0.122 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
N1 C1 1.402(10) . ?
N1 C8 1.408(14) . ?
N1 C9 1.560(13) . ?
N2 C16 1.383(9) . ?
N2 C17 1.426(9) . ?
N2 C25 1.454(8) . ?
O1 C1 1.185(9) . ?
O2 C9 1.206(14) . ?
O3 C9 1.279(14) . ?
O3 C10 1.476(14) . ?
O4 C26 1.336(7) . ?
O4 C27 1.489(7) . ?
O5 C26 1.192(8) . ?
O6 C21 1.369(9) . ?
O6 C38 1.419(13) . ?
O7 C22 1.374(10) . ?
O7 C39 1.379(11) . ?
C1 C2 1.536(7) . ?
C2 C3 1.509(8) . ?
C2 C14 1.542(7) . ?
C2 C25 1.583(7) . ?
C3 C4 1.383(12) . ?
C3 C8 1.406(12) . ?
C4 C5 1.416(14) . ?
C5 C6 1.42(2) . ?
C6 C7 1.397(17) . ?
C7 C8 1.390(13) . ?
C10 C12 1.43(2) . ?
C10 C13 1.517(19) . ?
C10 C11 1.52(3) . ?
C14 C15 1.520(8) . ?
C14 C26 1.532(8) . ?
C15 C16 1.333(9) . ?
C15 C31 1.515(9) . ?
C17 C18 1.520(13) . ?
C18 C19 1.534(11) . ?
C19 C24 1.379(10) . ?
C19 C20 1.383(11) . ?
C20 C21 1.396(12) . ?
C21 C22 1.385(11) . ?
C22 C23 1.360(9) . ?
C23 C24 1.417(10) . ?
C24 C25 1.501(8) . ?
C27 C30 1.496(12) . ?
C27 C29 1.502(11) . ?
C27 C28 1.536(13) . ?
C31 C32 1.518(10) . ?
C32 C33 1.380(12) . ?
C32 C37 1.387(11) . ?
C33 C34 1.357(15) . ?
C34 C35 1.379(17) . ?
C35 C36 1.348(18) . ?
C36 C37 1.391(14) . ?

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 C8 109.8(6) . . ?
C1 N1 C9 119.0(8) . . ?
C8 N1 C9 130.0(7) . . ?
C16 N2 C17 122.3(6) . . ?
C16 N2 C25 114.6(5) . . ?
C17 N2 C25 119.5(6) . . ?
C9 O3 C10 119.6(10) . . ?
C26 O4 C27 121.4(5) . . ?
C21 O6 C38 118.4(9) . . ?
C22 O7 C39 117.6(6) . . ?
O1 C1 N1 126.9(6) . . ?
O1 C1 C2 125.6(6) . . ?
N1 C1 C2 107.4(6) . . ?
C3 C2 C1 103.6(5) . . ?
C3 C2 C14 116.5(5) . . ?
C1 C2 C14 108.6(4) . . ?
C3 C2 C25 110.6(4) . . ?
C1 C2 C25 108.1(5) . . ?
C14 C2 C25 109.0(4) . . ?
C4 C3 C8 124.3(8) . . ?
C4 C3 C2 128.4(7) . . ?
C8 C3 C2 107.2(7) . . ?
C3 C4 C5 116.6(11) . . ?
C4 C5 C6 118.5(13) . . ?
C7 C6 C5 124.3(9) . . ?
C8 C7 C6 116.1(11) . . ?
C7 C8 C3 120.1(12) . . ?
C7 C8 N1 128.6(11) . . ?
C3 C8 N1 111.3(6) . . ?
O2 C9 O3 140.3(12) . . ?
O2 C9 N1 109.3(12) . . ?
O3 C9 N1 110.0(7) . . ?
C12 C10 O3 108.4(11) . . ?
C12 C10 C13 110.9(14) . . ?
O3 C10 C13 107.7(14) . . ?
C12 C10 C11 111.8(17) . . ?
O3 C10 C11 102.6(11) . . ?
C13 C10 C11 115.0(15) . . ?
C15 C14 C26 112.0(5) . . ?
C15 C14 C2 113.5(4) . . ?
C26 C14 C2 109.1(4) . . ?
C16 C15 C31 121.1(5) . . ?
C16 C15 C14 120.5(6) . . ?
C31 C15 C14 118.4(5) . . ?
C15 C16 N2 124.1(5) . . ?
N2 C17 C18 109.6(6) . . ?
C17 C18 C19 107.4(7) . . ?
C24 C19 C20 120.6(7) . . ?
C24 C19 C18 118.6(7) . . ?
C20 C19 C18 120.6(7) . . ?
C19 C20 C21 120.9(7) . . ?
O6 C21 C22 116.9(8) . . ?
O6 C21 C20 124.5(8) . . ?
C22 C21 C20 118.5(7) . . ?
C23 C22 O7 124.2(7) . . ?
C23 C22 C21 120.8(7) . . ?
O7 C22 C21 114.9(6) . . ?
C22 C23 C24 121.2(7) . . ?
C19 C24 C23 117.9(6) . . ?
C19 C24 C25 123.0(6) . . ?
C23 C24 C25 119.1(6) . . ?
N2 C25 C24 112.3(5) . . ?
N2 C25 C2 106.3(5) . . ?
C24 C25 C2 114.2(4) . . ?
O5 C26 O4 124.7(6) . . ?
O5 C26 C14 125.5(6) . . ?
O4 C26 C14 109.7(5) . . ?
O4 C27 C30 110.2(6) . . ?
O4 C27 C29 108.3(7) . . ?
C30 C27 C29 115.0(9) . . ?
O4 C27 C28 100.7(6) . . ?
C30 C27 C28 111.9(9) . . ?
C29 C27 C28 109.7(9) . . ?
C15 C31 C32 112.0(5) . . ?
C33 C32 C37 116.7(8) . . ?
C33 C32 C31 121.4(7) . . ?
C37 C32 C31 121.9(7) . . ?
C34 C33 C32 120.5(10) . . ?
C33 C34 C35 121.8(11) . . ?
C36 C35 C34 119.2(11) . . ?
C35 C36 C37 119.0(10) . . ?
C32 C37 C36 122.3(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 O1 175.4(7) . . . . ?
C9 N1 C1 O1 7.2(10) . . . . ?
C8 N1 C1 C2 -6.2(7) . . . . ?
C9 N1 C1 C2 -174.4(6) . . . . ?
O1 C1 C2 C3 -173.7(6) . . . . ?
N1 C1 C2 C3 7.8(6) . . . . ?
O1 C1 C2 C14 -49.3(8) . . . . ?
N1 C1 C2 C14 132.3(5) . . . . ?
O1 C1 C2 C25 68.8(8) . . . . ?
N1 C1 C2 C25 -109.6(5) . . . . ?
C1 C2 C3 C4 171.5(7) . . . . ?
C14 C2 C3 C4 52.4(9) . . . . ?
C25 C2 C3 C4 -72.9(9) . . . . ?
C1 C2 C3 C8 -6.7(6) . . . . ?
C14 C2 C3 C8 -125.8(5) . . . . ?
C25 C2 C3 C8 108.9(5) . . . . ?
C8 C3 C4 C5 -2.9(12) . . . . ?
C2 C3 C4 C5 179.2(8) . . . . ?
C3 C4 C5 C6 -0.4(14) . . . . ?
C4 C5 C6 C7 1.8(17) . . . . ?
C5 C6 C7 C8 0.1(15) . . . . ?
C6 C7 C8 C3 -3.2(12) . . . . ?
C6 C7 C8 N1 176.6(8) . . . . ?
C4 C3 C8 C7 4.9(11) . . . . ?
C2 C3 C8 C7 -176.8(7) . . . . ?
C4 C3 C8 N1 -175.0(7) . . . . ?
C2 C3 C8 N1 3.3(7) . . . . ?
C1 N1 C8 C7 -178.0(7) . . . . ?
C9 N1 C8 C7 -11.4(13) . . . . ?
C1 N1 C8 C3 1.9(8) . . . . ?
C9 N1 C8 C3 168.4(7) . . . . ?
C10 O3 C9 O2 -23(2) . . . . ?
C10 O3 C9 N1 165.8(9) . . . . ?
C1 N1 C9 O2 159.3(11) . . . . ?
C8 N1 C9 O2 -6.2(14) . . . . ?
C1 N1 C9 O3 -26.5(10) . . . . ?
C8 N1 C9 O3 168.1(8) . . . . ?
C9 O3 C10 C12 -55.8(17) . . . . ?
C9 O3 C10 C13 64.1(15) . . . . ?
C9 O3 C10 C11 -174.1(14) . . . . ?
C3 C2 C14 C15 -91.8(6) . . . . ?
C1 C2 C14 C15 151.8(5) . . . . ?
C25 C2 C14 C15 34.3(6) . . . . ?
C3 C2 C14 C26 33.9(6) . . . . ?
C1 C2 C14 C26 -82.5(6) . . . . ?
C25 C2 C14 C26 159.9(4) . . . . ?
C26 C14 C15 C16 -126.3(6) . . . . ?
C2 C14 C15 C16 -2.3(8) . . . . ?
C26 C14 C15 C31 54.5(7) . . . . ?
C2 C14 C15 C31 178.6(5) . . . . ?
C31 C15 C16 N2 175.1(6) . . . . ?
C14 C15 C16 N2 -4.0(10) . . . . ?
C17 N2 C16 C15 175.1(7) . . . . ?
C25 N2 C16 C15 -26.4(9) . . . . ?
C16 N2 C17 C18 -147.4(7) . . . . ?
C25 N2 C17 C18 55.1(10) . . . . ?
N2 C17 C18 C19 -59.4(9) . . . . ?
C17 C18 C19 C24 32.1(9) . . . . ?
C17 C18 C19 C20 -143.0(7) . . . . ?
C24 C19 C20 C21 -0.2(12) . . . . ?
C18 C19 C20 C21 174.9(7) . . . . ?
C38 O6 C21 C22 -179.9(9) . . . . ?
C38 O6 C21 C20 -4.4(13) . . . . ?
C19 C20 C21 O6 -176.1(8) . . . . ?
C19 C20 C21 C22 -0.7(12) . . . . ?
C39 O7 C22 C23 1.9(11) . . . . ?
C39 O7 C22 C21 177.7(7) . . . . ?
O6 C21 C22 C23 175.7(7) . . . . ?
C20 C21 C22 C23 -0.1(11) . . . . ?
O6 C21 C22 O7 -0.3(10) . . . . ?
C20 C21 C22 O7 -176.0(7) . . . . ?
O7 C22 C23 C24 177.2(6) . . . . ?
C21 C22 C23 C24 1.6(10) . . . . ?
C20 C19 C24 C23 1.6(10) . . . . ?
C18 C19 C24 C23 -173.5(6) . . . . ?
C20 C19 C24 C25 179.2(6) . . . . ?
C18 C19 C24 C25 4.1(10) . . . . ?
C22 C23 C24 C19 -2.4(9) . . . . ?
C22 C23 C24 C25 179.9(5) . . . . ?
C16 N2 C25 C24 -176.6(5) . . . . ?
C17 N2 C25 C24 -17.5(8) . . . . ?
C16 N2 C25 C2 57.8(7) . . . . ?
C17 N2 C25 C2 -143.1(6) . . . . ?
C19 C24 C25 N2 -13.6(8) . . . . ?
C23 C24 C25 N2 164.0(5) . . . . ?
C19 C24 C25 C2 107.6(7) . . . . ?
C23 C24 C25 C2 -74.8(7) . . . . ?
C3 C2 C25 N2 68.3(6) . . . . ?
C1 C2 C25 N2 -178.9(5) . . . . ?
C14 C2 C25 N2 -61.1(6) . . . . ?
C3 C2 C25 C24 -56.2(7) . . . . ?
C1 C2 C25 C24 56.6(6) . . . . ?
C14 C2 C25 C24 174.5(5) . . . . ?
C27 O4 C26 O5 2.3(10) . . . . ?
C27 O4 C26 C14 -177.1(5) . . . . ?
C15 C14 C26 O5 5.4(9) . . . . ?
C2 C14 C26 O5 -121.1(8) . . . . ?
C15 C14 C26 O4 -175.3(5) . . . . ?
C2 C14 C26 O4 58.2(6) . . . . ?
C26 O4 C27 C30 58.1(8) . . . . ?
C26 O4 C27 C29 -68.5(10) . . . . ?
C26 O4 C27 C28 176.4(8) . . . . ?
C16 C15 C31 C32 -124.9(7) . . . . ?
C14 C15 C31 C32 54.2(8) . . . . ?
C15 C31 C32 C33 68.7(9) . . . . ?
C15 C31 C32 C37 -110.1(8) . . . . ?
C37 C32 C33 C34 -6.2(15) . . . . ?
C31 C32 C33 C34 175.0(10) . . . . ?
C32 C33 C34 C35 7(2) . . . . ?
C33 C34 C35 C36 -2(2) . . . . ?
C34 C35 C36 C37 -4(2) . . . . ?
C33 C32 C37 C36 0.8(13) . . . . ?
C31 C32 C37 C36 179.7(9) . . . . ?
C35 C36 C37 C32 4.1(17) . . . . ?

_refine_diff_density_max         1.028
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.082

_shelxl_version_number           2013-2

