# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_Form_1F
_database_code_depnum_ccdc_archive 'CCDC 1545934'
_audit_update_record             
;
2017-04-25 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H38 N6 O8'
_chemical_formula_sum            'C30 H38 N6 O8'
_chemical_formula_weight         610.66

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

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

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

_cell_length_a                   8.5875(8)
_cell_length_b                   10.3508(8)
_cell_length_c                   10.6762(8)
_cell_angle_alpha                67.884(7)
_cell_angle_beta                 86.630(7)
_cell_angle_gamma                68.351(8)
_cell_volume                     813.60(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2403
_cell_measurement_theta_min      4.8450
_cell_measurement_theta_max      25.7160

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95852
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.4547
_diffrn_reflns_number            8314
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.248
_diffrn_reflns_theta_max         27.589
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.816
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.816
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3081
_reflns_number_gt                2051
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_structure_solution    SIR2014/14.10
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3081
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.43426(17) 0.37719(15) 0.61897(14) 0.0249(3) Uani 1 1 d . . . . .
N1 N 0.6528(2) 0.09288(18) 0.65905(16) 0.0225(4) Uani 1 1 d . . . . .
C1 C 0.5435(3) 0.3197(2) 0.7147(2) 0.0223(5) Uani 1 1 d . . . . .
O2 O 0.68641(18) 0.09339(15) 0.44658(14) 0.0297(4) Uani 1 1 d . . . . .
N2 N 0.8305(2) 0.30126(18) 0.36223(16) 0.0215(4) Uani 1 1 d . . . . .
C2 C 0.6634(3) 0.1560(2) 0.7575(2) 0.0237(5) Uani 1 1 d . . . . .
H2A H 0.7801 0.1495 0.7683 0.028 Uiso 1 1 calc R U . . .
H2B H 0.6364 0.0959 0.8465 0.028 Uiso 1 1 calc R U . . .
O3 O 0.75016(17) 0.44863(15) 0.14080(14) 0.0284(4) Uani 1 1 d . . . . .
N3 N 0.4336(2) 0.59856(18) 0.22087(16) 0.0214(4) Uani 1 1 d . . . . .
C3 C 0.5452(3) 0.0054(2) 0.6847(2) 0.0286(5) Uani 1 1 d . . . . .
H3A H 0.4284 0.0699 0.6897 0.034 Uiso 1 1 calc R U . . .
H3B H 0.5447 -0.0260 0.6079 0.034 Uiso 1 1 calc R U . . .
O4 O 0.06461(17) 0.72966(17) 0.19421(15) 0.0344(4) Uani 1 1 d . . . . .
C4 C 0.6021(3) -0.1282(2) 0.8110(2) 0.0274(5) Uani 1 1 d . . . . .
C5 C 0.6454(3) -0.2377(3) 0.9107(2) 0.0337(6) Uani 1 1 d . . . . .
H5 H 0.6804 -0.3262 0.9912 0.040 Uiso 1 1 calc R U . . .
C6 C 0.7057(2) 0.1384(2) 0.5326(2) 0.0234(5) Uani 1 1 d . . . . .
C7 C 0.7930(3) 0.2504(2) 0.5028(2) 0.0239(5) Uani 1 1 d . . . . .
H7A H 0.7194 0.3382 0.5230 0.029 Uiso 1 1 calc R U . . .
H7B H 0.8988 0.2021 0.5629 0.029 Uiso 1 1 calc R U . . .
C8 C 1.0062(3) 0.2457(2) 0.3348(2) 0.0276(5) Uani 1 1 d . . . . .
H8A H 1.0134 0.2834 0.2355 0.033 Uiso 1 1 calc R U . . .
H8B H 1.0503 0.1345 0.3699 0.033 Uiso 1 1 calc R U . . .
C9 C 1.1103(3) 0.2935(2) 0.3979(2) 0.0296(5) Uani 1 1 d . . . . .
C10 C 1.1909(3) 0.3320(3) 0.4514(2) 0.0401(6) Uani 1 1 d . . . . .
H10 H 1.2560 0.3631 0.4945 0.048 Uiso 1 1 calc R U . . .
C11 C 0.7122(3) 0.3972(2) 0.2576(2) 0.0217(5) Uani 1 1 d . . . . .
C12 C 0.5281(2) 0.4371(2) 0.2829(2) 0.0227(5) Uani 1 1 d . . . . .
H12A H 0.4793 0.3849 0.2454 0.027 Uiso 1 1 calc R U . . .
H12B H 0.5184 0.4018 0.3820 0.027 Uiso 1 1 calc R U . . .
C13 C 0.3228(3) 0.6595(2) 0.0966(2) 0.0241(5) Uani 1 1 d . . . . .
H13A H 0.3810 0.6081 0.0357 0.029 Uiso 1 1 calc R U . . .
H13B H 0.3031 0.7676 0.0496 0.029 Uiso 1 1 calc R U . . .
C14 C 0.1551(3) 0.6431(2) 0.1188(2) 0.0281(5) Uani 1 1 d . . . . .
H14A H 0.0911 0.6788 0.0303 0.034 Uiso 1 1 calc R U . . .
H14B H 0.1720 0.5360 0.1692 0.034 Uiso 1 1 calc R U . . .
C15 C -0.1016(3) 0.7310(3) 0.2091(3) 0.0458(7) Uani 1 1 d . . . . .
H15A H -0.1596 0.7918 0.2617 0.069 Uiso 1 1 calc R U . . .
H15B H -0.1630 0.7743 0.1193 0.069 Uiso 1 1 calc R U . . .
H15C H -0.0967 0.6279 0.2568 0.069 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.233(2) . ?
N1 C6 1.363(2) . ?
N1 C2 1.453(2) . ?
N1 C3 1.466(2) . ?
C1 N3 1.343(2) 2_666 ?
C1 C2 1.525(3) . ?
O2 C6 1.218(2) . ?
N2 C11 1.349(2) . ?
N2 C7 1.451(2) . ?
N2 C8 1.458(2) . ?
O3 C11 1.235(2) . ?
N3 C1 1.343(2) 2_666 ?
N3 C12 1.456(2) . ?
N3 C13 1.463(2) . ?
C3 C4 1.465(3) . ?
O4 C14 1.418(2) . ?
O4 C15 1.422(2) . ?
C4 C5 1.176(3) . ?
C6 C7 1.530(2) . ?
C8 C9 1.465(3) . ?
C9 C10 1.177(3) . ?
C11 C12 1.515(3) . ?
C13 C14 1.506(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C2 122.66(15) . . ?
C6 N1 C3 118.02(16) . . ?
C2 N1 C3 117.63(16) . . ?
O1 C1 N3 121.09(19) . 2_666 ?
O1 C1 C2 120.72(17) . . ?
N3 C1 C2 118.09(18) 2_666 . ?
C11 N2 C7 123.44(17) . . ?
C11 N2 C8 119.12(16) . . ?
C7 N2 C8 117.43(17) . . ?
N1 C2 C1 112.12(17) . . ?
C1 N3 C12 115.68(17) 2_666 . ?
C1 N3 C13 125.16(17) 2_666 . ?
C12 N3 C13 119.16(15) . . ?
C4 C3 N1 112.19(17) . . ?
C14 O4 C15 112.08(15) . . ?
C5 C4 C3 177.8(2) . . ?
O2 C6 N1 122.84(17) . . ?
O2 C6 C7 120.79(18) . . ?
N1 C6 C7 116.37(17) . . ?
N2 C7 C6 111.72(16) . . ?
N2 C8 C9 111.94(16) . . ?
C10 C9 C8 178.1(2) . . ?
O3 C11 N2 121.63(18) . . ?
O3 C11 C12 119.19(19) . . ?
N2 C11 C12 119.12(17) . . ?
N3 C12 C11 111.59(15) . . ?
N3 C13 C14 114.49(16) . . ?
O4 C14 C13 108.61(15) . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_form_1d
_database_code_depnum_ccdc_archive 'CCDC 1545932'
_audit_update_record             
;
2017-04-25 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;
_audit_creation_date             2017-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H38 N6 O8, 2(C H4 O)'
_chemical_formula_sum            'C32 H46 N6 O10'
_chemical_formula_weight         674.75
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5007(14)
_cell_length_b                   10.3965(11)
_cell_length_c                   10.9102(17)
_cell_angle_alpha                67.863(11)
_cell_angle_beta                 84.552(15)
_cell_angle_gamma                71.048(13)
_cell_volume                     844.3(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2468
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.4467
_cell_measurement_theta_min      2.0161
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7142
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_av_unetI/netI     0.1249
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6999
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.453
_diffrn_reflns_theta_min         2.016
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.889
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device_type  'Mercury2 (2x2 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2055
_reflns_number_total             3798
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2014 (Burla et al.. 2015)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3798
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1283
_refine_ls_R_factor_gt           0.0700
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0796P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.1966
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,
 H13B), C14(H14A,H14B)
2.b Me refined with riding coordinates:
 C15(H15A,H15B,H15C)
2.c Idealised Me refined with riding coordinates:
 C1S(H1SA,H1SB,H1SC)
2.d Idealised tetrahedral OH refined as rotating group:
 O1S(H1S)
2.e :
 C5(H5), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0679(2) 0.3765(2) 0.6197(2) 0.0239(5) Uani 1 1 d . . . . .
N1 N 0.1433(3) 0.1028(3) 0.6609(2) 0.0229(6) Uani 1 1 d . . . . .
C1 C 0.0357(4) 0.3280(3) 0.7106(3) 0.0226(6) Uani 1 1 d . . . . .
O2 O 0.1800(3) 0.0914(2) 0.4564(2) 0.0282(5) Uani 1 1 d . . . . .
N2 N 0.3346(3) 0.3027(3) 0.3598(2) 0.0234(6) Uani 1 1 d . . . . .
C2 C 0.1556(4) 0.1715(3) 0.7519(3) 0.0218(6) Uani 1 1 d . . . . .
H2A H 0.2710 0.1732 0.7543 0.026 Uiso 1 1 calc R . . . .
H2B H 0.1299 0.1131 0.8421 0.026 Uiso 1 1 calc R . . . .
O3 O 0.2620(3) 0.4491(2) 0.1450(2) 0.0279(5) Uani 1 1 d . . . . .
N3 N -0.0536(3) 0.5850(2) 0.2293(2) 0.0229(6) Uani 1 1 d . . . . .
C3 C 0.0357(4) 0.0099(3) 0.6971(3) 0.0255(7) Uani 1 1 d . . . . .
H3A H 0.0252 -0.0179 0.6216 0.031 Uiso 1 1 calc R . . . .
H3B H -0.0767 0.0663 0.7149 0.031 Uiso 1 1 calc R . . . .
O4 O -0.4214(3) 0.7019(2) 0.2012(2) 0.0301(5) Uani 1 1 d . . . . .
C4 C 0.1000(4) -0.1235(3) 0.8146(3) 0.0261(7) Uani 1 1 d . . . . .
C5 C 0.1475(4) -0.2333(3) 0.9091(3) 0.0331(8) Uani 1 1 d . . . . .
H5 H 0.1853 -0.3207 0.9845 0.040 Uiso 1 1 calc R . . . .
C6 C 0.2007(4) 0.1427(3) 0.5370(3) 0.0232(6) Uani 1 1 d . . . . .
C7 C 0.2915(4) 0.2568(3) 0.4996(3) 0.0238(7) Uani 1 1 d . . . . .
H7A H 0.2198 0.3434 0.5182 0.029 Uiso 1 1 calc R . . . .
H7B H 0.3945 0.2155 0.5553 0.029 Uiso 1 1 calc R . . . .
C8 C 0.5094(4) 0.2500(3) 0.3287(3) 0.0269(7) Uani 1 1 d . . . . .
H8A H 0.5223 0.2952 0.2322 0.032 Uiso 1 1 calc R . . . .
H8B H 0.5431 0.1428 0.3526 0.032 Uiso 1 1 calc R . . . .
C9 C 0.6193(4) 0.2843(3) 0.3995(3) 0.0287(7) Uani 1 1 d . . . . .
C10 C 0.7061(4) 0.3110(4) 0.4581(3) 0.0379(8) Uani 1 1 d . . . . .
H10 H 0.7762 0.3325 0.5054 0.045 Uiso 1 1 calc R . . . .
C11 C 0.2209(4) 0.3965(3) 0.2599(3) 0.0234(6) Uani 1 1 d . . . . .
C12 C 0.0379(4) 0.4298(3) 0.2907(3) 0.0243(7) Uani 1 1 d . . . . .
H12A H -0.0108 0.3732 0.2586 0.029 Uiso 1 1 calc R . . . .
H12B H 0.0258 0.3983 0.3878 0.029 Uiso 1 1 calc R . . . .
C13 C -0.1568(4) 0.6340(3) 0.1105(3) 0.0239(6) Uani 1 1 d . . . . .
H13A H -0.0952 0.5825 0.0520 0.029 Uiso 1 1 calc R . . . .
H13B H -0.1747 0.7398 0.0623 0.029 Uiso 1 1 calc R . . . .
C14 C -0.3236(4) 0.6093(3) 0.1360(3) 0.0263(7) Uani 1 1 d . . . . .
H14A H -0.3792 0.6319 0.0513 0.032 Uiso 1 1 calc R . . . .
H14B H -0.3094 0.5058 0.1920 0.032 Uiso 1 1 calc R . . . .
C15 C -0.5821(4) 0.6888(4) 0.2264(3) 0.0351(8) Uani 1 1 d . . . . .
H15A H -0.6449 0.7546 0.2714 0.053 Uiso 1 1 calc R . . . .
H15B H -0.6395 0.7150 0.1425 0.053 Uiso 1 1 calc R . . . .
H15C H -0.5737 0.5877 0.2828 0.053 Uiso 1 1 calc R . . . .
O1S O 0.4174(3) -0.0215(2) 0.2983(2) 0.0376(6) Uani 1 1 d . . . . .
H1S H 0.3425 0.0123 0.3441 0.056 Uiso 1 1 calc GR . . . .
C1S C 0.3808(5) 0.0654(4) 0.1629(3) 0.0409(9) Uani 1 1 d . . . . .
H1SA H 0.3177 0.1661 0.1536 0.061 Uiso 1 1 calc R . . . .
H1SB H 0.3145 0.0264 0.1258 0.061 Uiso 1 1 calc R . . . .
H1SC H 0.4848 0.0639 0.1154 0.061 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.231(3) . ?
N1 C2 1.452(3) . ?
N1 C3 1.464(3) . ?
N1 C6 1.350(4) . ?
C1 C2 1.531(4) . ?
C1 N3 1.351(4) 2_566 ?
O2 C6 1.238(3) . ?
N2 C7 1.465(4) . ?
N2 C8 1.462(4) . ?
N2 C11 1.363(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
O3 C11 1.232(3) . ?
N3 C1 1.351(4) 2_566 ?
N3 C12 1.458(4) . ?
N3 C13 1.462(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.472(4) . ?
O4 C14 1.417(3) . ?
O4 C15 1.407(3) . ?
C4 C5 1.192(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.529(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.469(4) . ?
C9 C10 1.178(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.514(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.504(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O1S H1S 0.8400 . ?
O1S C1S 1.411(4) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C3 117.3(2) . . ?
C6 N1 C2 122.2(2) . . ?
C6 N1 C3 119.3(2) . . ?
O1 C1 C2 121.0(2) . . ?
O1 C1 N3 120.5(3) . 2_566 ?
N3 C1 C2 118.3(3) 2_566 . ?
C8 N2 C7 117.6(2) . . ?
C11 N2 C7 122.9(2) . . ?
C11 N2 C8 119.4(2) . . ?
N1 C2 C1 111.5(2) . . ?
N1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C1 N3 C12 116.1(2) 2_566 . ?
C1 N3 C13 125.3(2) 2_566 . ?
C12 N3 C13 118.5(2) . . ?
N1 C3 H3A 109.1 . . ?
N1 C3 H3B 109.1 . . ?
N1 C3 C4 112.5(2) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C15 O4 C14 112.4(2) . . ?
C5 C4 C3 177.6(3) . . ?
C4 C5 H5 180.0 . . ?
N1 C6 C7 116.7(2) . . ?
O2 C6 N1 122.1(2) . . ?
O2 C6 C7 121.2(3) . . ?
N2 C7 C6 112.3(2) . . ?
N2 C7 H7A 109.1 . . ?
N2 C7 H7B 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
N2 C8 H8A 109.2 . . ?
N2 C8 H8B 109.2 . . ?
N2 C8 C9 112.1(3) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C10 C9 C8 178.9(3) . . ?
C9 C10 H10 180.0 . . ?
N2 C11 C12 118.5(2) . . ?
O3 C11 N2 122.2(3) . . ?
O3 C11 C12 119.2(3) . . ?
N3 C12 C11 112.1(2) . . ?
N3 C12 H12A 109.2 . . ?
N3 C12 H12B 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
N3 C13 H13A 108.6 . . ?
N3 C13 H13B 108.6 . . ?
N3 C13 C14 114.8(2) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
O4 C14 C13 108.3(2) . . ?
O4 C14 H14A 110.0 . . ?
O4 C14 H14B 110.0 . . ?
C13 C14 H14A 110.0 . . ?
C13 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1S O1S H1S 109.5 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N1 7.6(4) . . . . ?
N1 C6 C7 N2 -174.5(3) . . . . ?
C1 N3 C12 C11 -77.3(3) 2_566 . . . ?
C1 N3 C13 C14 -99.8(3) 2_566 . . . ?
O2 C6 C7 N2 4.7(4) . . . . ?
N2 C11 C12 N3 136.6(3) . . . . ?
C2 N1 C3 C4 -67.1(3) . . . . ?
C2 N1 C6 O2 -174.9(3) . . . . ?
C2 N1 C6 C7 4.4(4) . . . . ?
O3 C11 C12 N3 -46.7(3) . . . . ?
N3 C1 C2 N1 -168.1(2) 2_566 . . . ?
N3 C13 C14 O4 67.7(3) . . . . ?
C3 N1 C2 C1 -96.1(3) . . . . ?
C3 N1 C6 O2 -7.7(4) . . . . ?
C3 N1 C6 C7 171.6(2) . . . . ?
C6 N1 C2 C1 71.4(3) . . . . ?
C6 N1 C3 C4 125.1(3) . . . . ?
C7 N2 C8 C9 -54.4(3) . . . . ?
C7 N2 C11 O3 170.3(2) . . . . ?
C7 N2 C11 C12 -13.2(4) . . . . ?
C8 N2 C7 C6 -106.7(3) . . . . ?
C8 N2 C11 O3 -6.6(4) . . . . ?
C8 N2 C11 C12 169.9(2) . . . . ?
C11 N2 C7 C6 76.3(3) . . . . ?
C11 N2 C8 C9 122.7(3) . . . . ?
C12 N3 C13 C14 79.7(3) . . . . ?
C13 N3 C12 C11 103.2(3) . . . . ?
C15 O4 C14 C13 178.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile/methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_form_1C
_database_code_depnum_ccdc_archive 'CCDC 1545931'
_audit_update_record             
;
2017-04-25 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H38 N6 O8'
_chemical_formula_sum            'C30 H38 N6 O8'
_chemical_formula_weight         610.66

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

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

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

_cell_length_a                   8.814(3)
_cell_length_b                   9.0944(18)
_cell_length_c                   10.982(4)
_cell_angle_alpha                78.86(2)
_cell_angle_beta                 87.55(3)
_cell_angle_gamma                66.35(2)
_cell_volume                     790.6(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1844
_cell_measurement_theta_min      1.8914
_cell_measurement_theta_max      28.4967

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.051
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5331
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device_type  'Mercury2 (2x2 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 13.6612
_diffrn_reflns_number            6474
_diffrn_reflns_av_unetI/netI     0.1002
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.891
_diffrn_reflns_theta_max         28.499
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             3541
_reflns_number_gt                1454
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    SIR2014/14.10
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1113P)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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.027(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3541
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1766
_refine_ls_R_factor_gt           0.0762
_refine_ls_wR_factor_ref         0.2567
_refine_ls_wR_factor_gt          0.1880
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_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 -0.0735(3) -0.1026(3) 0.4133(2) 0.0581(7) Uani 1 1 d . . . . .
N1 N 0.1603(3) -0.2095(4) 0.2434(3) 0.0494(8) Uani 1 1 d . . . . .
C1 C 0.0337(4) -0.2405(5) 0.4472(3) 0.0478(9) Uani 1 1 d . . . . .
O2 O 0.1979(3) 0.0159(3) 0.1454(2) 0.0610(8) Uani 1 1 d . . . . .
N2 N 0.3545(3) 0.0403(4) 0.3504(3) 0.0473(8) Uani 1 1 d . . . . .
C2 C 0.1658(4) -0.3221(5) 0.3584(3) 0.0515(9) Uani 1 1 d . . . . .
H2A H 0.2768 -0.3640 0.3997 0.062 Uiso 1 1 calc R U . . .
H2B H 0.1487 -0.4164 0.3392 0.062 Uiso 1 1 calc R U . . .
O3 O 0.2887(3) 0.2942(3) 0.3842(3) 0.0618(8) Uani 1 1 d . . . . .
N3 N -0.0382(3) 0.3254(4) 0.4362(3) 0.0495(8) Uani 1 1 d . . . . .
C3 C 0.0567(5) -0.2006(5) 0.1406(4) 0.0623(11) Uani 1 1 d . . . . .
H3A H 0.0093 -0.0865 0.0937 0.075 Uiso 1 1 calc R U . . .
H3B H -0.0366 -0.2279 0.1745 0.075 Uiso 1 1 calc R U . . .
O4 O 0.1857(5) -0.4733(5) 0.1135(3) 0.1077(13) Uani 1 1 d . . . . .
C4 C 0.1443(7) -0.3105(7) 0.0535(5) 0.0879(15) Uani 1 1 d . . . . .
H4A H 0.0721 -0.2848 -0.0210 0.105 Uiso 1 1 calc R U . . .
H4B H 0.2461 -0.2945 0.0265 0.105 Uiso 1 1 calc R U . . .
C5 C 0.2627(9) -0.5870(8) 0.0360(6) 0.134(2) Uani 1 1 d . . . . .
H5A H 0.2885 -0.6980 0.0828 0.200 Uiso 1 1 calc R U . . .
H5B H 0.1878 -0.5647 -0.0351 0.200 Uiso 1 1 calc R U . . .
H5C H 0.3653 -0.5774 0.0061 0.200 Uiso 1 1 calc R U . . .
C6 C 0.2170(4) -0.0906(5) 0.2385(3) 0.0496(9) Uani 1 1 d . . . . .
C7 C 0.3089(4) -0.0985(4) 0.3545(3) 0.0511(9) Uani 1 1 d . . . . .
H7A H 0.2386 -0.1042 0.4265 0.061 Uiso 1 1 calc R U . . .
H7B H 0.4110 -0.2005 0.3680 0.061 Uiso 1 1 calc R U . . .
C8 C 0.5309(4) 0.0081(5) 0.3403(4) 0.0572(10) Uani 1 1 d . . . . .
H8A H 0.5963 -0.0918 0.4009 0.069 Uiso 1 1 calc R U . . .
H8B H 0.5500 0.1005 0.3614 0.069 Uiso 1 1 calc R U . . .
C9 C 0.5881(4) -0.0134(6) 0.2150(4) 0.0675(12) Uani 1 1 d . . . . .
C10 C 0.6317(6) -0.0274(9) 0.1148(5) 0.106(2) Uani 1 1 d . . . . .
H10 H 0.6673 -0.0387 0.0329 0.127 Uiso 1 1 calc R U . . .
C11 C 0.2456(4) 0.1877(5) 0.3647(3) 0.0497(9) Uani 1 1 d . . . . .
C12 C 0.0612(4) 0.2296(5) 0.3477(4) 0.0550(10) Uani 1 1 d . . . . .
H12A H 0.0232 0.2919 0.2624 0.066 Uiso 1 1 calc R U . . .
H12B H 0.0439 0.1270 0.3573 0.066 Uiso 1 1 calc R U . . .
C13 C -0.1706(4) 0.4833(5) 0.3881(3) 0.0537(10) Uani 1 1 d . . . . .
H13A H -0.1282 0.5445 0.3208 0.064 Uiso 1 1 calc R U . . .
H13B H -0.2061 0.5473 0.4552 0.064 Uiso 1 1 calc R U . . .
C14 C -0.3135(5) 0.4660(5) 0.3400(4) 0.0622(11) Uani 1 1 d . . . . .
C15 C -0.4247(6) 0.4455(7) 0.3015(5) 0.0945(17) Uani 1 1 d . . . . .
H15 H -0.5144 0.4289 0.2704 0.113 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.226(4) . ?
N1 C6 1.353(4) . ?
N1 C3 1.452(4) . ?
N1 C2 1.453(5) . ?
C1 N3 1.354(5) 2_556 ?
C1 C2 1.532(5) . ?
O2 C6 1.230(4) . ?
N2 C11 1.334(5) . ?
N2 C7 1.463(4) . ?
N2 C8 1.465(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
O3 C11 1.228(4) . ?
N3 C1 1.354(5) 2_556 ?
N3 C12 1.453(4) . ?
N3 C13 1.455(5) . ?
C3 C4 1.483(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
O4 C4 1.403(6) . ?
O4 C5 1.409(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.513(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.467(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.164(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.525(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.462(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.178(6) . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C3 118.8(3) . . ?
C6 N1 C2 121.7(3) . . ?
C3 N1 C2 117.9(3) . . ?
O1 C1 N3 121.0(3) . 2_556 ?
O1 C1 C2 120.8(4) . . ?
N3 C1 C2 118.1(3) 2_556 . ?
C11 N2 C7 122.9(3) . . ?
C11 N2 C8 119.9(3) . . ?
C7 N2 C8 116.9(3) . . ?
N1 C2 C1 112.0(3) . . ?
N1 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C1 N3 C12 115.5(3) 2_556 . ?
C1 N3 C13 123.1(3) 2_556 . ?
C12 N3 C13 118.2(3) . . ?
N1 C3 C4 114.4(4) . . ?
N1 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
N1 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C4 O4 C5 113.2(5) . . ?
O4 C4 C3 109.1(4) . . ?
O4 C4 H4A 109.9 . . ?
C3 C4 H4A 109.9 . . ?
O4 C4 H4B 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
O4 C5 H5A 109.5 . . ?
O4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O2 C6 N1 122.5(3) . . ?
O2 C6 C7 121.8(3) . . ?
N1 C6 C7 115.7(3) . . ?
N2 C7 C6 114.2(3) . . ?
N2 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
N2 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N2 C8 C9 111.9(3) . . ?
N2 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N2 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 178.7(6) . . ?
C9 C10 H10 180.0 . . ?
O3 C11 N2 122.4(3) . . ?
O3 C11 C12 118.7(4) . . ?
N2 C11 C12 118.8(3) . . ?
N3 C12 C11 112.6(3) . . ?
N3 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
N3 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
N3 C13 C14 112.0(3) . . ?
N3 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N3 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 177.3(5) . . ?
C14 C15 H15 180.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C1 74.4(4) . . . . ?
C3 N1 C2 C1 -90.8(4) . . . . ?
O1 C1 C2 N1 8.4(5) . . . . ?
N3 C1 C2 N1 -171.9(3) 2_556 . . . ?
C6 N1 C3 C4 101.6(4) . . . . ?
C2 N1 C3 C4 -92.7(4) . . . . ?
C5 O4 C4 C3 177.1(4) . . . . ?
N1 C3 C4 O4 69.0(5) . . . . ?
C3 N1 C6 O2 -7.2(5) . . . . ?
C2 N1 C6 O2 -172.3(3) . . . . ?
C3 N1 C6 C7 173.9(3) . . . . ?
C2 N1 C6 C7 8.8(5) . . . . ?
C11 N2 C7 C6 75.9(4) . . . . ?
C8 N2 C7 C6 -109.4(3) . . . . ?
O2 C6 C7 N2 6.6(5) . . . . ?
N1 C6 C7 N2 -174.4(3) . . . . ?
C11 N2 C8 C9 -110.7(4) . . . . ?
C7 N2 C8 C9 74.4(4) . . . . ?
C7 N2 C11 O3 166.2(3) . . . . ?
C8 N2 C11 O3 -8.5(5) . . . . ?
C7 N2 C11 C12 -18.1(5) . . . . ?
C8 N2 C11 C12 167.3(3) . . . . ?
C1 N3 C12 C11 -76.7(4) 2_556 . . . ?
C13 N3 C12 C11 122.9(3) . . . . ?
O3 C11 C12 N3 -42.5(5) . . . . ?
N2 C11 C12 N3 141.6(3) . . . . ?
C1 N3 C13 C14 -84.1(4) 2_556 . . . ?
C12 N3 C13 C14 74.7(4) . . . . ?

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.053


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile/water'
####################################################################### 
# 
# 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_form_1e
_database_code_depnum_ccdc_archive 'CCDC 1545933'
_audit_update_record             
;
2017-04-25 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;
_audit_creation_date             2017-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H38 N6 O8, 1.16(H2 O)'
_chemical_formula_sum            'C30 H40.32 N6 O9.16'
_chemical_formula_weight         631.56
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5852(15)
_cell_length_b                   10.4929(17)
_cell_length_c                   10.556(2)
_cell_angle_alpha                68.110(9)
_cell_angle_beta                 86.318(10)
_cell_angle_gamma                67.035(9)
_cell_volume                     808.8(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1146
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.19
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_av_unetI/netI     0.1266
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5511
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.712
_diffrn_reflns_theta_min         2.089
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.945




_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'




_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1780
_reflns_number_total             3240
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1183
_refine_ls_R_factor_gt           0.0582
_refine_ls_restrained_S_all      0.925
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0681P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1560
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Sof(O1W)=Sof(H1WA)=Sof(H1WB)=FVAR(1)
3.a Free rotating group:
 O1W(H1WA,H1WB)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,
 H13B), C14(H14A,H14B)
3.c Me refined with riding coordinates:
 C15(H15A,H15B,H15C)
3.d :
 C5(H5), C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4342(2) 0.3797(2) 0.6167(2) 0.0233(5) Uani 1 1 d . . . . .
N1 N 0.6540(3) 0.0963(3) 0.6499(2) 0.0236(6) Uani 1 1 d . . . . .
C1 C 0.5472(4) 0.3181(3) 0.7130(3) 0.0212(6) Uani 1 1 d . . . . .
O2 O 0.6921(3) 0.0952(2) 0.4363(2) 0.0290(5) Uani 1 1 d . . . . .
N2 N 0.8315(3) 0.3030(3) 0.3547(2) 0.0207(6) Uani 1 1 d . . . . .
C2 C 0.6681(4) 0.1541(3) 0.7532(3) 0.0233(7) Uani 1 1 d . . . . .
H2A H 0.7864 0.1443 0.7641 0.028 Uiso 1 1 calc R . . . .
H2B H 0.6416 0.0938 0.8424 0.028 Uiso 1 1 calc R . . . .
O3 O 0.7455(2) 0.4613(2) 0.1341(2) 0.0274(5) Uani 1 1 d . . . . .
N3 N 0.4266(3) 0.6042(3) 0.2203(2) 0.0214(6) Uani 1 1 d . . . . .
C3 C 0.5481(4) 0.0105(3) 0.6747(3) 0.0288(7) Uani 1 1 d . . . . .
H3A H 0.5542 -0.0248 0.5988 0.035 Uiso 1 1 calc R . . . .
H3B H 0.4285 0.0771 0.6739 0.035 Uiso 1 1 calc R . . . .
O4 O 0.0534(3) 0.7337(3) 0.1943(2) 0.0343(6) Uani 1 1 d . . . . .
C4 C 0.5984(4) -0.1188(4) 0.8050(3) 0.0265(7) Uani 1 1 d . . . . .
C5 C 0.6364(4) -0.2263(4) 0.9071(3) 0.0320(8) Uani 1 1 d . . . . .
H5 H 0.6670 -0.3128 0.9893 0.038 Uiso 1 1 calc R . . . .
C6 C 0.7093(4) 0.1403(3) 0.5244(3) 0.0214(7) Uani 1 1 d . . . . .
C7 C 0.7973(4) 0.2481(3) 0.4963(3) 0.0227(7) Uani 1 1 d . . . . .
H7A H 0.7246 0.3340 0.5206 0.027 Uiso 1 1 calc R . . . .
H7B H 0.9057 0.1966 0.5555 0.027 Uiso 1 1 calc R . . . .
C8 C 1.0100(3) 0.2520(3) 0.3255(3) 0.0268(7) Uani 1 1 d . . . . .
H8A H 1.0605 0.1414 0.3595 0.032 Uiso 1 1 calc R . . . .
H8B H 1.0159 0.2909 0.2250 0.032 Uiso 1 1 calc R . . . .
C9 C 1.1082(4) 0.3017(4) 0.3894(3) 0.0284(7) Uani 1 1 d . . . . .
C10 C 1.1856(4) 0.3424(4) 0.4440(3) 0.0369(8) Uani 1 1 d . . . . .
H10 H 1.2475 0.3749 0.4878 0.044 Uiso 1 1 calc R . . . .
C11 C 0.7105(4) 0.4044(3) 0.2508(3) 0.0213(7) Uani 1 1 d . . . . .
C12 C 0.5253(3) 0.4431(3) 0.2776(3) 0.0226(7) Uani 1 1 d . . . . .
H12A H 0.4772 0.3940 0.2366 0.027 Uiso 1 1 calc R . . . .
H12B H 0.5171 0.4043 0.3778 0.027 Uiso 1 1 calc R . . . .
C13 C 0.3130(3) 0.6713(3) 0.0923(3) 0.0243(7) Uani 1 1 d . . . . .
H13A H 0.3724 0.6238 0.0279 0.029 Uiso 1 1 calc R . . . .
H13B H 0.2910 0.7790 0.0491 0.029 Uiso 1 1 calc R . . . .
C14 C 0.1465(4) 0.6556(4) 0.1124(3) 0.0293(8) Uani 1 1 d . . . . .
H14A H 0.0811 0.6962 0.0224 0.035 Uiso 1 1 calc R . . . .
H14B H 0.1662 0.5486 0.1576 0.035 Uiso 1 1 calc R . . . .
C15 C -0.1106(4) 0.7296(5) 0.2079(4) 0.0525(11) Uani 1 1 d . . . . .
H15A H -0.1727 0.7846 0.2651 0.079 Uiso 1 1 calc R . . . .
H15B H -0.1733 0.7759 0.1170 0.079 Uiso 1 1 calc R . . . .
H15C H -0.0990 0.6255 0.2508 0.079 Uiso 1 1 calc R . . . .
O1W O 0.9044(5) 0.0454(5) 0.2217(5) 0.0431(16) Uani 0.580(7) 1 d . . P . .
H1WA H 0.8277 0.0686 0.2764 0.065 Uiso 0.580(7) 1 d G . P . .
H1WB H 0.9117 -0.0368 0.2148 0.065 Uiso 0.580(7) 1 d G . P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.240(3) . ?
N1 C2 1.462(3) . ?
N1 C3 1.463(4) . ?
N1 C6 1.352(4) . ?
C1 C2 1.529(4) . ?
C1 N3 1.344(3) 2_666 ?
O2 C6 1.230(3) . ?
N2 C7 1.445(4) . ?
N2 C8 1.467(4) . ?
N2 C11 1.352(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
O3 C11 1.228(3) . ?
N3 C1 1.344(3) 2_666 ?
N3 C12 1.458(4) . ?
N3 C13 1.482(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.465(4) . ?
O4 C14 1.410(3) . ?
O4 C15 1.422(4) . ?
C4 C5 1.179(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.525(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.455(4) . ?
C9 C10 1.188(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.515(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.495(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O1W H1WA 0.8701 . ?
O1W H1WB 0.8699 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C3 117.8(2) . . ?
C6 N1 C2 122.5(2) . . ?
C6 N1 C3 118.7(2) . . ?
O1 C1 C2 121.0(2) . . ?
O1 C1 N3 120.9(3) . 2_666 ?
N3 C1 C2 117.9(2) 2_666 . ?
C7 N2 C8 117.1(2) . . ?
C11 N2 C7 123.8(2) . . ?
C11 N2 C8 119.0(2) . . ?
N1 C2 C1 111.5(2) . . ?
N1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C1 N3 C12 115.8(2) 2_666 . ?
C1 N3 C13 124.7(2) 2_666 . ?
C12 N3 C13 119.4(2) . . ?
N1 C3 H3A 108.9 . . ?
N1 C3 H3B 108.9 . . ?
N1 C3 C4 113.4(2) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C14 O4 C15 111.1(2) . . ?
C5 C4 C3 176.9(3) . . ?
C4 C5 H5 180.0 . . ?
N1 C6 C7 117.0(2) . . ?
O2 C6 N1 122.2(3) . . ?
O2 C6 C7 120.7(3) . . ?
N2 C7 C6 112.5(2) . . ?
N2 C7 H7A 109.1 . . ?
N2 C7 H7B 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
N2 C8 H8A 109.2 . . ?
N2 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 N2 111.9(2) . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C10 C9 C8 178.4(3) . . ?
C9 C10 H10 180.0 . . ?
N2 C11 C12 118.8(2) . . ?
O3 C11 N2 122.2(3) . . ?
O3 C11 C12 118.9(3) . . ?
N3 C12 C11 111.6(2) . . ?
N3 C12 H12A 109.3 . . ?
N3 C12 H12B 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N3 C13 H13A 108.7 . . ?
N3 C13 H13B 108.7 . . ?
N3 C13 C14 114.3(2) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
O4 C14 C13 109.6(2) . . ?
O4 C14 H14A 109.8 . . ?
O4 C14 H14B 109.8 . . ?
C13 C14 H14A 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H1WA O1W H1WB 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N1 11.5(4) . . . . ?
N1 C6 C7 N2 -172.5(2) . . . . ?
C1 N3 C12 C11 -73.0(3) 2_666 . . . ?
C1 N3 C13 C14 -103.3(3) 2_666 . . . ?
O2 C6 C7 N2 8.3(4) . . . . ?
N2 C11 C12 N3 134.5(2) . . . . ?
C2 N1 C3 C4 -56.3(3) . . . . ?
C2 N1 C6 O2 -177.5(2) . . . . ?
C2 N1 C6 C7 3.3(4) . . . . ?
O3 C11 C12 N3 -48.6(3) . . . . ?
N3 C1 C2 N1 -164.6(2) 2_666 . . . ?
N3 C13 C14 O4 63.5(3) . . . . ?
C3 N1 C2 C1 -98.2(3) . . . . ?
C3 N1 C6 O2 -9.4(4) . . . . ?
C3 N1 C6 C7 171.4(2) . . . . ?
C6 N1 C2 C1 70.0(3) . . . . ?
C6 N1 C3 C4 135.0(3) . . . . ?
C7 N2 C8 C9 -63.2(3) . . . . ?
C7 N2 C11 O3 171.7(2) . . . . ?
C7 N2 C11 C12 -11.5(4) . . . . ?
C8 N2 C7 C6 -110.9(3) . . . . ?
C8 N2 C11 O3 -4.0(4) . . . . ?
C8 N2 C11 C12 172.9(2) . . . . ?
C11 N2 C7 C6 73.3(3) . . . . ?
C11 N2 C8 C9 112.7(3) . . . . ?
C12 N3 C13 C14 79.8(3) . . . . ?
C13 N3 C12 C11 104.2(3) . . . . ?
C15 O4 C14 C13 176.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
