# Electronic Supplementary Material (ESI) for ChemComm.
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1487433'
_audit_update_record             
;
2016-06-23 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;

_chemical_compound_source        'Nathalie Busschaert'

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 N O5'
_chemical_formula_sum            'C13 H15 N O5'
_chemical_formula_weight         265.26

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

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

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

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

_cell_length_a                   24.202(5)
_cell_length_b                   4.5207(10)
_cell_length_c                   24.218(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.835(3)
_cell_angle_gamma                90
_cell_volume                     2442.0(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6673
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      25.12

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32397
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.521
_diffrn_reflns_theta_max         26.420
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5023
_reflns_number_gt                4406
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin. Twin matrix 0 0 -1 0 -1 0 -1 0 0
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0807P)²+0.7522P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5023
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1430
_refine_ls_wR_factor_gt          0.1376
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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
C1 C 0.50720(15) 0.9481(8) 0.74688(15) 0.0352(8) Uani 1 1 d . . . . .
H1A H 0.4816 1.0071 0.7060 0.053 Uiso 1 1 calc R U . . .
H1B H 0.4828 0.8510 0.7657 0.053 Uiso 1 1 calc R U . . .
H1C H 0.5264 1.1236 0.7701 0.053 Uiso 1 1 calc R U . . .
C2 C 0.55429(16) 0.7379(7) 0.74507(15) 0.0278(7) Uani 1 1 d . . . . .
C3 C 0.58605(14) 0.4692(6) 0.67342(13) 0.0229(6) Uani 1 1 d . . . . .
C4 C 0.64523(14) 0.4185(7) 0.71050(13) 0.0258(7) Uani 1 1 d . . . . .
H4 H 0.6621 0.5192 0.7478 0.031 Uiso 1 1 calc R U . . .
C5 C 0.68033(14) 0.2226(7) 0.69409(14) 0.0236(7) Uani 1 1 d . . . . .
H5 H 0.7207 0.1883 0.7204 0.028 Uiso 1 1 calc R U . . .
C6 C 0.65668(14) 0.0761(7) 0.63940(14) 0.0242(6) Uani 1 1 d . . . . .
C7 C 0.59689(14) 0.1287(6) 0.60236(13) 0.0235(6) Uani 1 1 d . . . . .
H7 H 0.5802 0.0286 0.5650 0.028 Uiso 1 1 calc R U . . .
C8 C 0.56134(14) 0.3202(7) 0.61805(14) 0.0253(7) Uani 1 1 d . . . . .
C9 C 0.69146(14) -0.1336(7) 0.61868(14) 0.0255(6) Uani 1 1 d . . . . .
C10 C 0.78507(15) -0.3749(8) 0.64381(16) 0.0333(7) Uani 1 1 d . . . . .
H10A H 0.8245 -0.3877 0.6768 0.050 Uiso 1 1 calc R U . . .
H10B H 0.7665 -0.5713 0.6359 0.050 Uiso 1 1 calc R U . . .
H10C H 0.7897 -0.3022 0.6077 0.050 Uiso 1 1 calc R U . . .
C11 C 0.49649(14) 0.3527(7) 0.57768(14) 0.0265(7) Uani 1 1 d . . . . .
H11 H 0.4878 0.2305 0.5408 0.032 Uiso 1 1 calc R U . . .
C12 C 0.40735(15) 0.4513(8) 0.58824(16) 0.0325(7) Uani 1 1 d . . . . .
H12A H 0.4064 0.5713 0.6221 0.039 Uiso 1 1 calc R U . . .
H12B H 0.3696 0.3366 0.5710 0.039 Uiso 1 1 calc R U . . .
C13 C 0.41561(14) 0.6446(7) 0.54153(15) 0.0302(7) Uani 1 1 d . . . . .
H13A H 0.3962 0.5577 0.5010 0.036 Uiso 1 1 calc R U . . .
H13B H 0.3994 0.8457 0.5416 0.036 Uiso 1 1 calc R U . . .
N1 N 0.55073(12) 0.6726(6) 0.68919(12) 0.0256(6) Uani 1 1 d . . . . .
H1N H 0.5184(16) 0.743(8) 0.6591(17) 0.026(9) Uiso 1 1 d . . . . .
O1 O 0.59201(11) 0.6323(5) 0.79117(10) 0.0342(6) Uani 1 1 d . . . . .
O2 O 0.67328(10) -0.2523(6) 0.57056(10) 0.0327(6) Uani 1 1 d . . . . .
O3 O 0.74760(9) -0.1745(5) 0.65991(10) 0.0294(5) Uani 1 1 d . . . . .
O4 O 0.45890(10) 0.2568(5) 0.60771(10) 0.0264(5) Uani 1 1 d . . . . .
O5 O 0.48039(10) 0.6491(5) 0.56105(10) 0.0277(5) Uani 1 1 d . . . . .
C14 C 0.24412(15) 0.9833(8) 0.50274(15) 0.0335(8) Uani 1 1 d . . . . .
H14A H 0.2032 1.0311 0.4752 0.050 Uiso 1 1 calc R U . . .
H14B H 0.2655 1.1660 0.5203 0.050 Uiso 1 1 calc R U . . .
H14C H 0.2651 0.8819 0.4808 0.050 Uiso 1 1 calc R U . . .
C15 C 0.24197(14) 0.7848(7) 0.55174(15) 0.0254(7) Uani 1 1 d . . . . .
C16 C 0.16932(14) 0.5235(6) 0.58426(13) 0.0230(6) Uani 1 1 d . . . . .
C17 C 0.20587(13) 0.4977(7) 0.64499(14) 0.0250(6) Uani 1 1 d . . . . .
H17 H 0.2419 0.6092 0.6613 0.030 Uiso 1 1 calc R U . . .
C18 C 0.18995(14) 0.3111(7) 0.68131(14) 0.0239(6) Uani 1 1 d . . . . .
H18 H 0.2157 0.2898 0.7223 0.029 Uiso 1 1 calc R U . . .
C19 C 0.13612(14) 0.1526(7) 0.65839(14) 0.0234(6) Uani 1 1 d . . . . .
C20 C 0.09996(13) 0.1800(6) 0.59787(13) 0.0218(6) Uani 1 1 d . . . . .
H20 H 0.0637 0.0702 0.5819 0.026 Uiso 1 1 calc R U . . .
C21 C 0.11524(13) 0.3619(6) 0.56041(14) 0.0224(6) Uani 1 1 d . . . . .
C22 C 0.11669(14) -0.0473(6) 0.69602(14) 0.0247(6) Uani 1 1 d . . . . .
C23 C 0.14443(15) -0.2750(8) 0.79126(14) 0.0300(7) Uani 1 1 d . . . . .
H23A H 0.1784 -0.2858 0.8300 0.045 Uiso 1 1 calc R U . . .
H23B H 0.1094 -0.1955 0.7971 0.045 Uiso 1 1 calc R U . . .
H23C H 0.1352 -0.4734 0.7738 0.045 Uiso 1 1 calc R U . . .
C24 C 0.07569(13) 0.3616(6) 0.49491(14) 0.0227(6) Uani 1 1 d . . . . .
H24 H 0.0399 0.2337 0.4879 0.027 Uiso 1 1 calc R U . . .
C25 C 0.09111(15) 0.4297(7) 0.40709(14) 0.0295(7) Uani 1 1 d . . . . .
H25A H 0.0770 0.3040 0.3708 0.035 Uiso 1 1 calc R U . . .
H25B H 0.1251 0.5520 0.4074 0.035 Uiso 1 1 calc R U . . .
C26 C 0.04096(15) 0.6212(7) 0.40965(14) 0.0294(7) Uani 1 1 d . . . . .
H26A H 0.0401 0.8163 0.3908 0.035 Uiso 1 1 calc R U . . .
H26B H 0.0015 0.5238 0.3898 0.035 Uiso 1 1 calc R U . . .
N2 N 0.18422(12) 0.7152(6) 0.54579(12) 0.0234(6) Uani 1 1 d . . . . .
H2N H 0.1524(18) 0.781(9) 0.5163(17) 0.033(10) Uiso 1 1 d . . . . .
O6 O 0.28633(10) 0.6931(6) 0.59163(11) 0.0380(6) Uani 1 1 d . . . . .
O7 O 0.06808(10) -0.1645(5) 0.67987(11) 0.0324(5) Uani 1 1 d . . . . .
O8 O 0.15959(10) -0.0825(5) 0.75114(9) 0.0296(5) Uani 1 1 d . . . . .
O9 O 0.10799(10) 0.2529(5) 0.46051(10) 0.0257(5) Uani 1 1 d . . . . .
O10 O 0.05681(9) 0.6490(5) 0.47307(9) 0.0253(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.497(5) . ?
C2 O1 1.232(4) . ?
C2 N1 1.355(4) . ?
C3 C4 1.383(4) . ?
C3 N1 1.406(4) . ?
C3 C8 1.410(4) . ?
C4 C5 1.388(4) . ?
C5 C6 1.390(4) . ?
C6 C7 1.396(4) . ?
C6 C9 1.479(4) . ?
C7 C8 1.374(4) . ?
C8 C11 1.500(4) . ?
C9 O2 1.201(4) . ?
C9 O3 1.351(4) . ?
C10 O3 1.439(4) . ?
C11 O5 1.410(4) . ?
C11 O4 1.435(4) . ?
C12 O4 1.447(4) . ?
C12 C13 1.503(5) . ?
C13 O5 1.451(4) . ?
C14 C15 1.505(4) . ?
C15 O6 1.205(4) . ?
C15 N2 1.384(4) . ?
C16 C17 1.396(4) . ?
C16 C21 1.412(4) . ?
C16 N2 1.418(4) . ?
C17 C18 1.377(4) . ?
C18 C19 1.399(4) . ?
C19 C20 1.391(4) . ?
C19 C22 1.483(4) . ?
C20 C21 1.377(4) . ?
C21 C24 1.501(4) . ?
C22 O7 1.209(4) . ?
C22 O8 1.345(4) . ?
C23 O8 1.453(4) . ?
C24 O10 1.411(4) . ?
C24 O9 1.432(4) . ?
C25 O9 1.438(4) . ?
C25 C26 1.511(5) . ?
C26 O10 1.437(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C2 N1 123.9(3) . . ?
O1 C2 C1 121.6(3) . . ?
N1 C2 C1 114.4(3) . . ?
C4 C3 N1 121.2(3) . . ?
C4 C3 C8 119.3(3) . . ?
N1 C3 C8 119.5(3) . . ?
C3 C4 C5 121.0(3) . . ?
C4 C5 C6 120.4(3) . . ?
C5 C6 C7 118.2(3) . . ?
C5 C6 C9 123.4(3) . . ?
C7 C6 C9 118.4(3) . . ?
C8 C7 C6 122.3(3) . . ?
C7 C8 C3 119.0(3) . . ?
C7 C8 C11 119.4(3) . . ?
C3 C8 C11 121.6(3) . . ?
O2 C9 O3 122.8(3) . . ?
O2 C9 C6 125.0(3) . . ?
O3 C9 C6 112.2(3) . . ?
O5 C11 O4 105.8(2) . . ?
O5 C11 C8 112.5(3) . . ?
O4 C11 C8 110.4(2) . . ?
O4 C12 C13 104.4(3) . . ?
O5 C13 C12 101.9(2) . . ?
C2 N1 C3 127.2(3) . . ?
C9 O3 C10 116.4(2) . . ?
C11 O4 C12 106.7(2) . . ?
C11 O5 C13 102.9(2) . . ?
O6 C15 N2 123.7(3) . . ?
O6 C15 C14 123.0(3) . . ?
N2 C15 C14 113.3(3) . . ?
C17 C16 C21 119.7(3) . . ?
C17 C16 N2 121.6(3) . . ?
C21 C16 N2 118.6(3) . . ?
C18 C17 C16 120.3(3) . . ?
C17 C18 C19 120.6(3) . . ?
C20 C19 C18 118.7(3) . . ?
C20 C19 C22 118.8(3) . . ?
C18 C19 C22 122.4(3) . . ?
C21 C20 C19 121.8(3) . . ?
C20 C21 C16 118.9(3) . . ?
C20 C21 C24 118.1(3) . . ?
C16 C21 C24 122.8(3) . . ?
O7 C22 O8 123.3(3) . . ?
O7 C22 C19 124.7(3) . . ?
O8 C22 C19 112.0(3) . . ?
O10 C24 O9 105.6(2) . . ?
O10 C24 C21 112.1(2) . . ?
O9 C24 C21 110.3(2) . . ?
O9 C25 C26 103.5(2) . . ?
O10 C26 C25 102.0(2) . . ?
C15 N2 C16 125.1(3) . . ?
C22 O8 C23 115.9(2) . . ?
C24 O9 C25 107.7(2) . . ?
C24 O10 C26 103.5(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O5 0.89(4) 2.23(4) 2.905(4) 132(3) .
N2 H2N O9 0.87(4) 2.53(4) 3.259(3) 141(3) 1_565
N2 H2N O10 0.87(4) 2.22(4) 2.913(3) 136(3) .

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.066



####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1487434'
_audit_update_record             
;
2016-06-23 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;

_chemical_compound_source        'Nathalie Busschaert'

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H20 N2 O3'
_chemical_formula_sum            'C15 H20 N2 O3'
_chemical_formula_weight         276.33

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                   10.9082(7)
_cell_length_b                   10.9750(7)
_cell_length_c                   12.5933(8)
_cell_angle_alpha                79.4910(10)
_cell_angle_beta                 80.0990(10)
_cell_angle_gamma                89.4990(10)
_cell_volume                     1459.87(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5188
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      26.35

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19880
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.670
_diffrn_reflns_theta_max         26.405
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5979
_reflns_number_gt                4594
_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.

 Pseudosymmetry might be present. Monoclinic C space groups can be found from the data, but structure solving and refinement is not possible in this space group. PLATON ADDSYMM did not find higher symmmetry.
;

_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-97 (Sheldrick, 2008)'
_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)+(0.0850P)²+0.2434P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5979
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1471
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
C1 C 0.34440(15) 0.41429(14) 0.52621(12) 0.0254(3) Uani 1 1 d . . . . .
H1A H 0.4285 0.4008 0.4886 0.038 Uiso 1 1 calc R U . . .
H1B H 0.3047 0.3343 0.5627 0.038 Uiso 1 1 calc R U . . .
H1C H 0.2951 0.4557 0.4726 0.038 Uiso 1 1 calc R U . . .
C2 C 0.24149(14) 0.51617(13) 0.66401(11) 0.0213(3) Uani 1 1 d . . . . .
C3 C 0.25384(14) 0.58991(13) 0.74951(11) 0.0206(3) Uani 1 1 d . . . . .
C4 C 0.14674(14) 0.60819(13) 0.82235(12) 0.0210(3) Uani 1 1 d . . . . .
H4 H 0.0696 0.5738 0.8151 0.025 Uiso 1 1 calc R U . . .
C5 C 0.14982(13) 0.67549(13) 0.90526(12) 0.0206(3) Uani 1 1 d . . . . .
C6 C 0.26512(13) 0.72749(13) 0.91565(11) 0.0197(3) Uani 1 1 d . . . . .
C7 C 0.37315(14) 0.70828(13) 0.84271(12) 0.0217(3) Uani 1 1 d . . . . .
H7 H 0.4507 0.7425 0.8491 0.026 Uiso 1 1 calc R U . . .
C8 C 0.36723(13) 0.63966(13) 0.76147(12) 0.0217(3) Uani 1 1 d . . . . .
H8 H 0.4412 0.6263 0.7133 0.026 Uiso 1 1 calc R U . . .
C9 C 0.36285(14) 0.85019(13) 1.02904(12) 0.0220(3) Uani 1 1 d . . . . .
C10 C 0.32646(14) 0.92654(14) 1.11700(12) 0.0258(3) Uani 1 1 d . . . . .
H10A H 0.2357 0.9243 1.1383 0.039 Uiso 1 1 calc R U . . .
H10B H 0.3643 0.8925 1.1810 0.039 Uiso 1 1 calc R U . . .
H10C H 0.3558 1.0124 1.0890 0.039 Uiso 1 1 calc R U . . .
C11 C 0.03107(14) 0.68541(14) 0.97891(12) 0.0230(3) Uani 1 1 d . . . . .
H11 H -0.0389 0.6404 0.9692 0.028 Uiso 1 1 calc R U . . .
C12 C -0.10998(14) 0.74733(14) 1.11978(12) 0.0255(3) Uani 1 1 d . . . . .
H12A H -0.1064 0.7109 1.1971 0.031 Uiso 1 1 calc R U . . .
H12B H -0.1653 0.6934 1.0928 0.031 Uiso 1 1 calc R U . . .
C13 C -0.16496(14) 0.87564(15) 1.11468(12) 0.0259(4) Uani 1 1 d . . . . .
H13 H -0.1631 0.9133 1.0359 0.031 Uiso 1 1 calc R U . . .
C14 C -0.30094(15) 0.86493(17) 1.17279(13) 0.0336(4) Uani 1 1 d . . . . .
H14A H -0.3477 0.8106 1.1395 0.050 Uiso 1 1 calc R U . . .
H14B H -0.3047 0.8300 1.2507 0.050 Uiso 1 1 calc R U . . .
H14C H -0.3374 0.9473 1.1653 0.050 Uiso 1 1 calc R U . . .
C15 C -0.08891(15) 0.95928(15) 1.16387(13) 0.0301(4) Uani 1 1 d . . . . .
H15A H -0.1263 1.0412 1.1595 0.045 Uiso 1 1 calc R U . . .
H15B H -0.0879 0.9229 1.2408 0.045 Uiso 1 1 calc R U . . .
H15C H -0.0035 0.9677 1.1230 0.045 Uiso 1 1 calc R U . . .
N1 N 0.26380(12) 0.79736(11) 0.99821(10) 0.0216(3) Uani 1 1 d . . . . .
N2 N 0.01491(11) 0.74967(12) 1.05464(10) 0.0233(3) Uani 1 1 d . . . . .
O1 O 0.35168(9) 0.49126(10) 0.60698(8) 0.0243(3) Uani 1 1 d . . . . .
O2 O 0.14354(10) 0.48029(11) 0.64741(9) 0.0312(3) Uani 1 1 d . . . . .
O3 O 0.47115(10) 0.83832(10) 0.98875(9) 0.0300(3) Uani 1 1 d . . . . .
H1N H 0.1876(19) 0.8051(18) 1.0350(16) 0.042(5) Uiso 1 1 d . . . . .
C16 C 0.35792(14) 0.40131(14) 0.02218(12) 0.0254(3) Uani 1 1 d . . . . .
H16A H 0.4422 0.3844 -0.0126 0.038 Uiso 1 1 calc R U . . .
H16B H 0.3133 0.3228 0.0555 0.038 Uiso 1 1 calc R U . . .
H16C H 0.3135 0.4475 -0.0332 0.038 Uiso 1 1 calc R U . . .
C17 C 0.25454(13) 0.50284(13) 0.15937(12) 0.0207(3) Uani 1 1 d . . . . .
C18 C 0.26597(13) 0.57960(13) 0.24292(11) 0.0203(3) Uani 1 1 d . . . . .
C19 C 0.15671(14) 0.61539(15) 0.30247(13) 0.0272(4) Uani 1 1 d . . . . .
H19 H 0.0790 0.5881 0.2898 0.033 Uiso 1 1 calc R U . . .
C20 C 0.15842(14) 0.69036(15) 0.38030(13) 0.0282(4) Uani 1 1 d . . . . .
C21 C 0.27418(14) 0.72824(13) 0.40146(12) 0.0216(3) Uani 1 1 d . . . . .
C22 C 0.38413(14) 0.69253(14) 0.34099(12) 0.0218(3) Uani 1 1 d . . . . .
H22 H 0.4624 0.7184 0.3537 0.026 Uiso 1 1 calc R U . . .
C23 C 0.37952(14) 0.61967(14) 0.26272(12) 0.0218(3) Uani 1 1 d . . . . .
H23 H 0.4549 0.5966 0.2219 0.026 Uiso 1 1 calc R U . . .
C24 C 0.36958(14) 0.84572(13) 0.51982(12) 0.0221(3) Uani 1 1 d . . . . .
C25 C 0.33262(15) 0.92949(14) 0.60183(13) 0.0269(4) Uani 1 1 d . . . . .
H25A H 0.2420 0.9379 0.6141 0.040 Uiso 1 1 calc R U . . .
H25B H 0.3592 0.8938 0.6712 0.040 Uiso 1 1 calc R U . . .
H25C H 0.3727 1.0113 0.5735 0.040 Uiso 1 1 calc R U . . .
C29 C -0.29354(15) 0.83166(18) 0.67549(14) 0.0375(4) Uani 1 1 d . . . . .
H29A H -0.3420 0.7978 0.6284 0.056 Uiso 1 1 calc R U . A 1
H29B H -0.3264 0.7974 0.7525 0.056 Uiso 1 1 calc R U . A 1
H29C H -0.2997 0.9221 0.6630 0.056 Uiso 1 1 calc R U . A 1
C26A C 0.03749(18) 0.7367(2) 0.42462(19) 0.0205(5) Uani 0.779(3) 1 d . . P B 1
H26A H -0.0341 0.7077 0.4022 0.025 Uiso 0.779(3) 1 calc R U P B 1
C27A C -0.10754(16) 0.84703(17) 0.52673(15) 0.0213(5) Uani 0.779(3) 1 d . . P B
1
H27A H -0.1621 0.8151 0.4822 0.026 Uiso 0.779(3) 1 calc R U P B 1
H27B H -0.1125 0.9385 0.5134 0.026 Uiso 0.779(3) 1 calc R U P B 1
C28A C -0.1553(2) 0.7963(3) 0.6480(2) 0.0238(5) Uani 0.779(3) 1 d . . P B 1
H28A H -0.1497 0.7039 0.6615 0.029 Uiso 0.779(3) 1 calc R U P B 1
C30A C -0.0790(2) 0.8482(2) 0.72026(17) 0.0331(6) Uani 0.779(3) 1 d . . P B 1
H30A H -0.1115 0.8142 0.7974 0.050 Uiso 0.779(3) 1 calc R U P B 1
H30B H 0.0081 0.8251 0.7024 0.050 Uiso 0.779(3) 1 calc R U P B 1
H30C H -0.0843 0.9387 0.7076 0.050 Uiso 0.779(3) 1 calc R U P B 1
N4A N 0.02075(14) 0.81284(17) 0.49092(15) 0.0208(4) Uani 0.779(3) 1 d . . P B 1
C26B C 0.0356(7) 0.6788(9) 0.4746(7) 0.0254(18) Uani 0.221(3) 1 d . . P B 2
H26B H -0.0279 0.6204 0.4742 0.030 Uiso 0.221(3) 1 calc R U P B 2
C27B C -0.1048(7) 0.7382(8) 0.6166(6) 0.0286(19) Uani 0.221(3) 1 d . . P B 2
H27C H -0.0990 0.7033 0.6937 0.034 Uiso 0.221(3) 1 calc R U P B 2
H27D H -0.1595 0.6822 0.5912 0.034 Uiso 0.221(3) 1 calc R U P B 2
C28B C -0.1609(7) 0.8629(10) 0.6108(6) 0.0265(19) Uani 0.221(3) 1 d . . P B 2
H28B H -0.1656 0.8986 0.5327 0.032 Uiso 0.221(3) 1 calc R U P B 2
C30B C -0.0883(7) 0.9524(7) 0.6573(7) 0.035(2) Uani 0.221(3) 1 d . . P B 2
H30D H -0.1291 1.0326 0.6515 0.053 Uiso 0.221(3) 1 calc R U P B 2
H30E H -0.0857 0.9188 0.7345 0.053 Uiso 0.221(3) 1 calc R U P B 2
H30F H -0.0032 0.9633 0.6159 0.053 Uiso 0.221(3) 1 calc R U P B 2
N4B N 0.0204(5) 0.7437(7) 0.5487(6) 0.0248(17) Uani 0.221(3) 1 d . . P B 2
N3 N 0.27163(12) 0.80287(12) 0.48070(10) 0.0241(3) Uani 1 1 d . . . . .
O4 O 0.36496(9) 0.47413(10) 0.10616(8) 0.0244(3) Uani 1 1 d . . . . .
O5 O 0.15640(10) 0.46957(10) 0.14045(9) 0.0272(3) Uani 1 1 d . . . . .
O6 O 0.47770(10) 0.82085(10) 0.49090(9) 0.0300(3) Uani 1 1 d . . . . .
H3N H 0.191(2) 0.8213(19) 0.5095(16) 0.049(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.4481(16) . ?
C2 O2 1.2061(18) . ?
C2 O1 1.3432(17) . ?
C2 C3 1.4839(19) . ?
C3 C4 1.393(2) . ?
C3 C8 1.399(2) . ?
C4 C5 1.3895(19) . ?
C5 C6 1.422(2) . ?
C5 C11 1.4735(19) . ?
C6 N1 1.3981(18) . ?
C6 C7 1.404(2) . ?
C7 C8 1.3866(19) . ?
C9 O3 1.2188(18) . ?
C9 N1 1.3754(19) . ?
C9 C10 1.506(2) . ?
C11 N2 1.2742(18) . ?
C12 N2 1.4623(18) . ?
C12 C13 1.521(2) . ?
C13 C15 1.521(2) . ?
C13 C14 1.532(2) . ?
C16 O4 1.4493(16) . ?
C17 O5 1.2094(17) . ?
C17 O4 1.3387(17) . ?
C17 C18 1.4840(19) . ?
C18 C19 1.389(2) . ?
C18 C23 1.395(2) . ?
C19 C20 1.392(2) . ?
C20 C21 1.415(2) . ?
C20 C26A 1.466(2) . ?
C20 C26B 1.619(8) . ?
C21 N3 1.3984(18) . ?
C21 C22 1.399(2) . ?
C22 C23 1.3853(19) . ?
C24 O6 1.2170(18) . ?
C24 N3 1.3712(19) . ?
C24 C25 1.507(2) . ?
C29 C28B 1.541(8) . ?
C29 C28A 1.551(3) . ?
C26A N4A 1.276(2) . ?
C27A N4A 1.462(2) . ?
C27A C28A 1.527(3) . ?
C28A C30A 1.517(3) . ?
C26B N4B 1.261(9) . ?
C27B N4B 1.476(9) . ?
C27B C28B 1.489(12) . ?
C28B C30B 1.523(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C2 O1 122.79(13) . . ?
O2 C2 C3 124.22(13) . . ?
O1 C2 C3 112.98(12) . . ?
C4 C3 C8 118.80(13) . . ?
C4 C3 C2 117.81(13) . . ?
C8 C3 C2 123.38(13) . . ?
C5 C4 C3 121.67(13) . . ?
C4 C5 C6 119.13(13) . . ?
C4 C5 C11 116.56(13) . . ?
C6 C5 C11 124.30(13) . . ?
N1 C6 C7 123.43(13) . . ?
N1 C6 C5 117.40(13) . . ?
C7 C6 C5 119.16(13) . . ?
C8 C7 C6 120.33(14) . . ?
C7 C8 C3 120.88(13) . . ?
O3 C9 N1 123.72(14) . . ?
O3 C9 C10 122.09(13) . . ?
N1 C9 C10 114.19(13) . . ?
N2 C11 C5 125.09(13) . . ?
N2 C12 C13 112.56(12) . . ?
C15 C13 C12 111.20(13) . . ?
C15 C13 C14 111.19(13) . . ?
C12 C13 C14 109.81(13) . . ?
C9 N1 C6 128.47(13) . . ?
C11 N2 C12 117.10(12) . . ?
C2 O1 C1 114.88(11) . . ?
O5 C17 O4 123.06(13) . . ?
O5 C17 C18 124.08(13) . . ?
O4 C17 C18 112.86(12) . . ?
C19 C18 C23 118.69(13) . . ?
C19 C18 C17 117.57(13) . . ?
C23 C18 C17 123.71(13) . . ?
C18 C19 C20 121.55(14) . . ?
C19 C20 C21 119.28(14) . . ?
C19 C20 C26A 115.71(14) . . ?
C21 C20 C26A 124.57(14) . . ?
C19 C20 C26B 115.2(3) . . ?
C21 C20 C26B 120.2(3) . . ?
N3 C21 C22 123.53(13) . . ?
N3 C21 C20 117.40(13) . . ?
C22 C21 C20 119.04(13) . . ?
C23 C22 C21 120.38(13) . . ?
C22 C23 C18 121.03(13) . . ?
O6 C24 N3 123.94(13) . . ?
O6 C24 C25 121.93(13) . . ?
N3 C24 C25 114.12(13) . . ?
N4A C26A C20 125.14(17) . . ?
N4A C27A C28A 112.76(17) . . ?
C30A C28A C27A 111.16(18) . . ?
C30A C28A C29 110.11(18) . . ?
C27A C28A C29 108.46(19) . . ?
C26A N4A C27A 116.95(16) . . ?
N4B C26B C20 123.1(6) . . ?
N4B C27B C28B 111.8(6) . . ?
C27B C28B C30B 112.9(7) . . ?
C27B C28B C29 102.1(7) . . ?
C30B C28B C29 113.8(5) . . ?
C26B N4B C27B 116.5(6) . . ?
C24 N3 C21 128.55(13) . . ?
C17 O4 C16 114.61(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N N2 0.89(2) 1.95(2) 2.7157(18) 143.8(17) .
N3 H3N N4A 0.93(2) 1.91(2) 2.720(2) 143.8(17) .
N3 H3N N4B 0.93(2) 1.99(2) 2.773(6) 140.1(17) .

_refine_diff_density_max         0.360
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.052



####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1487435'
_audit_update_record             
;
2016-06-23 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;

_chemical_compound_source        'Nathalie Busschaert'
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H34 N4 O4'
_chemical_formula_sum            'C27 H34 N4 O4'
_chemical_formula_weight         478.58

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                   7.1080(14)
_cell_length_b                   13.001(3)
_cell_length_c                   15.084(3)
_cell_angle_alpha                112.002(3)
_cell_angle_beta                 102.265(3)
_cell_angle_gamma                90.523(3)
_cell_volume                     1256.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6525
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      27.10

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21850
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.497
_diffrn_reflns_theta_max         27.150
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5526
_reflns_number_gt                4262
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.1003P)²+0.8103P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5526
_refine_ls_number_parameters     324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1939
_refine_ls_wR_factor_gt          0.1825
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
C1 C 0.1181(3) 0.7430(2) 0.24493(17) 0.0275(5) Uani 1 1 d . . . . .
H1A H 0.0735 0.6663 0.1987 0.041 Uiso 1 1 calc R U . . .
H1B H 0.0129 0.7906 0.2413 0.041 Uiso 1 1 calc R U . . .
H1C H 0.2286 0.7703 0.2278 0.041 Uiso 1 1 calc R U . . .
C2 C 0.1786(3) 0.74576(18) 0.34809(17) 0.0251(5) Uani 1 1 d . . . . .
C3 C 0.2137(3) 0.61150(18) 0.43214(16) 0.0224(4) Uani 1 1 d . . . . .
C4 C 0.1743(3) 0.49853(18) 0.41614(15) 0.0219(4) Uani 1 1 d . . . . .
C5 C 0.2319(3) 0.46388(18) 0.49420(16) 0.0224(4) Uani 1 1 d . . . . .
H5 H 0.2055 0.3877 0.4830 0.027 Uiso 1 1 calc R U . . .
C6 C 0.3266(3) 0.53737(17) 0.58766(15) 0.0215(4) Uani 1 1 d . . . . .
C7 C 0.3623(3) 0.64894(18) 0.60191(16) 0.0245(5) Uani 1 1 d . . . . .
H7 H 0.4267 0.7007 0.6653 0.029 Uiso 1 1 calc R U . . .
C8 C 0.3071(3) 0.68628(18) 0.52688(16) 0.0257(5) Uani 1 1 d . . . . .
H8 H 0.3323 0.7629 0.5393 0.031 Uiso 1 1 calc R U . . .
C9 C 0.3895(3) 0.50477(18) 0.67401(16) 0.0221(4) Uani 1 1 d . . . . .
C10 C 0.3707(3) 0.34054(18) 0.72027(15) 0.0216(4) Uani 1 1 d . . . . .
C11 C 0.3181(3) 0.22328(18) 0.68015(16) 0.0229(4) Uani 1 1 d . . . . .
C12 C 0.3400(3) 0.16724(18) 0.74394(16) 0.0239(5) Uani 1 1 d . . . . .
H12 H 0.3066 0.0890 0.7176 0.029 Uiso 1 1 calc R U . . .
C13 C 0.4091(3) 0.22235(18) 0.84474(16) 0.0239(5) Uani 1 1 d . . . . .
C14 C 0.4585(3) 0.33695(19) 0.88312(16) 0.0247(5) Uani 1 1 d . . . . .
H14 H 0.5052 0.3754 0.9521 0.030 Uiso 1 1 calc R U . . .
C15 C 0.4409(3) 0.39606(18) 0.82249(16) 0.0243(5) Uani 1 1 d . . . . .
H15 H 0.4762 0.4742 0.8500 0.029 Uiso 1 1 calc R U . . .
C16 C 0.4238(3) 0.15447(19) 0.90652(16) 0.0250(5) Uani 1 1 d . . . . .
C17 C 0.4847(4) 0.1577(2) 1.06733(17) 0.0299(5) Uani 1 1 d . . . . .
H17A H 0.5175 0.2105 1.1360 0.045 Uiso 1 1 calc R U . . .
H17B H 0.3611 0.1144 1.0540 0.045 Uiso 1 1 calc R U . . .
H17C H 0.5863 0.1072 1.0555 0.045 Uiso 1 1 calc R U . . .
C18 C 0.0738(3) 0.41263(18) 0.32159(16) 0.0238(5) Uani 1 1 d . . . . .
H18 H 0.0537 0.3390 0.3186 0.029 Uiso 1 1 calc R U . . .
C19 C -0.0794(3) 0.33329(19) 0.15478(16) 0.0275(5) Uani 1 1 d . . . . .
H19A H -0.2069 0.3501 0.1246 0.033 Uiso 1 1 calc R U . . .
H19B H -0.1006 0.2690 0.1728 0.033 Uiso 1 1 calc R U . . .
C20 C 0.0487(3) 0.3033(2) 0.08056(17) 0.0302(5) Uani 1 1 d . . . . .
H20 H 0.1799 0.2926 0.1142 0.036 Uiso 1 1 calc R U . . .
C21 C -0.0343(4) 0.1939(2) -0.00549(19) 0.0381(6) Uani 1 1 d . . . . .
H21A H -0.0472 0.1351 0.0193 0.057 Uiso 1 1 calc R U . . .
H21B H -0.1616 0.2032 -0.0406 0.057 Uiso 1 1 calc R U . . .
H21C H 0.0528 0.1732 -0.0505 0.057 Uiso 1 1 calc R U . . .
C22 C 0.0706(4) 0.3961(2) 0.04465(19) 0.0394(6) Uani 1 1 d . . . . .
H22A H 0.1240 0.4654 0.1010 0.059 Uiso 1 1 calc R U . . .
H22B H 0.1582 0.3765 -0.0001 0.059 Uiso 1 1 calc R U . . .
H22C H -0.0562 0.4065 0.0099 0.059 Uiso 1 1 calc R U . . .
C23 C 0.2339(3) 0.15701(18) 0.57590(16) 0.0249(5) Uani 1 1 d . . . . .
H23 H 0.2099 0.0787 0.5563 0.030 Uiso 1 1 calc R U . . .
C24 C 0.0963(3) 0.12159(19) 0.41016(16) 0.0282(5) Uani 1 1 d . . . . .
H24A H -0.0315 0.1464 0.3904 0.034 Uiso 1 1 calc R U . . .
H24B H 0.0745 0.0457 0.4090 0.034 Uiso 1 1 calc R U . . .
C25 C 0.2170(4) 0.11750(18) 0.33636(16) 0.0272(5) Uani 1 1 d . . . . .
H25 H 0.2637 0.1957 0.3493 0.033 Uiso 1 1 calc R U . . .
C26 C 0.3930(4) 0.0537(2) 0.3487(2) 0.0357(6) Uani 1 1 d . . . . .
H26A H 0.4703 0.0882 0.4165 0.053 Uiso 1 1 calc R U . . .
H26B H 0.3502 -0.0239 0.3344 0.053 Uiso 1 1 calc R U . . .
H26C H 0.4717 0.0559 0.3033 0.053 Uiso 1 1 calc R U . . .
C27 C 0.0933(4) 0.0656(2) 0.23123(17) 0.0387(6) Uani 1 1 d . . . . .
H27A H -0.0189 0.1076 0.2247 0.058 Uiso 1 1 calc R U . . .
H27B H 0.1706 0.0678 0.1852 0.058 Uiso 1 1 calc R U . . .
H27C H 0.0491 -0.0120 0.2163 0.058 Uiso 1 1 calc R U . . .
N1 N 0.1586(3) 0.64259(16) 0.35198(14) 0.0238(4) Uani 1 1 d . . . . .
N2 N 0.3449(3) 0.39417(15) 0.65493(14) 0.0231(4) Uani 1 1 d . . . . .
N3 N 0.0114(3) 0.42983(15) 0.24308(13) 0.0253(4) Uani 1 1 d . . . . .
N4 N 0.1905(3) 0.19691(15) 0.50970(13) 0.0251(4) Uani 1 1 d . . . . .
O1 O 0.2399(3) 0.83155(14) 0.41944(12) 0.0342(4) Uani 1 1 d . . . . .
O2 O 0.4731(2) 0.57320(13) 0.75474(11) 0.0294(4) Uani 1 1 d . . . . .
O3 O 0.4686(2) 0.21816(13) 1.00313(11) 0.0269(4) Uani 1 1 d . . . . .
O4 O 0.3975(3) 0.05395(14) 0.87350(12) 0.0339(4) Uani 1 1 d . . . . .
H1N H 0.105(5) 0.586(3) 0.299(2) 0.045(9) Uiso 1 1 d . . . . .
H2N H 0.290(4) 0.349(3) 0.590(2) 0.045(8) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.510(3) . ?
C2 O1 1.218(3) . ?
C2 N1 1.372(3) . ?
C3 N1 1.395(3) . ?
C3 C8 1.404(3) . ?
C3 C4 1.411(3) . ?
C4 C5 1.397(3) . ?
C4 C18 1.467(3) . ?
C5 C6 1.389(3) . ?
C6 C7 1.397(3) . ?
C6 C9 1.498(3) . ?
C7 C8 1.377(3) . ?
C9 O2 1.224(3) . ?
C9 N2 1.376(3) . ?
C10 N2 1.390(3) . ?
C10 C15 1.407(3) . ?
C10 C11 1.426(3) . ?
C11 C12 1.395(3) . ?
C11 C23 1.466(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.392(3) . ?
C13 C16 1.495(3) . ?
C14 C15 1.386(3) . ?
C16 O4 1.208(3) . ?
C16 O3 1.343(3) . ?
C17 O3 1.447(3) . ?
C18 N3 1.275(3) . ?
C19 N3 1.460(3) . ?
C19 C20 1.532(3) . ?
C20 C22 1.516(4) . ?
C20 C21 1.527(3) . ?
C23 N4 1.273(3) . ?
C24 N4 1.456(3) . ?
C24 C25 1.530(3) . ?
C25 C26 1.524(3) . ?
C25 C27 1.529(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
O1 C2 N1 124.4(2) . . ?
O1 C2 C1 122.6(2) . . ?
N1 C2 C1 113.01(19) . . ?
N1 C3 C8 123.47(19) . . ?
N1 C3 C4 117.77(19) . . ?
C8 C3 C4 118.76(19) . . ?
C5 C4 C3 119.32(19) . . ?
C5 C4 C18 116.44(19) . . ?
C3 C4 C18 124.24(19) . . ?
C6 C5 C4 122.03(19) . . ?
C5 C6 C7 117.60(19) . . ?
C5 C6 C9 124.14(19) . . ?
C7 C6 C9 118.25(19) . . ?
C8 C7 C6 122.0(2) . . ?
C7 C8 C3 120.3(2) . . ?
O2 C9 N2 123.8(2) . . ?
O2 C9 C6 121.28(19) . . ?
N2 C9 C6 114.91(18) . . ?
N2 C10 C15 123.57(19) . . ?
N2 C10 C11 117.18(19) . . ?
C15 C10 C11 119.23(19) . . ?
C12 C11 C10 118.57(19) . . ?
C12 C11 C23 116.92(19) . . ?
C10 C11 C23 124.45(19) . . ?
C13 C12 C11 122.0(2) . . ?
C12 C13 C14 118.9(2) . . ?
C12 C13 C16 117.6(2) . . ?
C14 C13 C16 123.5(2) . . ?
C15 C14 C13 121.2(2) . . ?
C14 C15 C10 120.1(2) . . ?
O4 C16 O3 123.8(2) . . ?
O4 C16 C13 124.0(2) . . ?
O3 C16 C13 112.23(19) . . ?
N3 C18 C4 124.6(2) . . ?
N3 C19 C20 110.53(19) . . ?
C22 C20 C21 110.8(2) . . ?
C22 C20 C19 111.1(2) . . ?
C21 C20 C19 110.1(2) . . ?
N4 C23 C11 124.7(2) . . ?
N4 C24 C25 111.96(19) . . ?
C26 C25 C27 110.7(2) . . ?
C26 C25 C24 111.0(2) . . ?
C27 C25 C24 110.5(2) . . ?
C2 N1 C3 129.21(19) . . ?
C9 N2 C10 128.65(19) . . ?
C18 N3 C19 117.01(19) . . ?
C23 N4 C24 118.45(19) . . ?
C16 O3 C17 115.14(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N N3 0.86(3) 1.93(3) 2.694(3) 147(3) .
N2 H2N N4 0.92(3) 1.93(3) 2.701(3) 140(3) .

_refine_diff_density_max         0.464
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.066



####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1487436'
_audit_update_record             
;
2016-06-23 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;

_chemical_compound_source        'Nathalie Busschaert'
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H32 N2 O12'
_chemical_formula_sum            'C27 H32 N2 O12'
_chemical_formula_weight         576.54

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

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

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

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

_cell_length_a                   14.5173(5)
_cell_length_b                   12.8034(4)
_cell_length_c                   14.6624(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.9480(10)
_cell_angle_gamma                90
_cell_volume                     2620.42(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      26.37

_exptl_crystal_description       fragment
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46815
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.748
_diffrn_reflns_theta_max         26.394
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5361
_reflns_number_gt                4418
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.0814P)²+1.1103P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5361
_refine_ls_number_parameters     374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1360
_refine_ls_wR_factor_gt          0.1280
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.88759(12) -0.40624(13) 0.58263(12) 0.0237(4) Uani 1 1 d . . . . .
C2 C 0.88856(12) -0.41910(13) 0.48899(12) 0.0248(4) Uani 1 1 d . . . . .
H2 H 0.8956 -0.4868 0.4653 0.030 Uiso 1 1 calc R U . . .
C3 C 0.87924(12) -0.33325(13) 0.43030(12) 0.0236(3) Uani 1 1 d . . . . .
H3 H 0.8787 -0.3419 0.3658 0.028 Uiso 1 1 calc R U . . .
C4 C 0.87052(11) -0.23346(12) 0.46572(11) 0.0204(3) Uani 1 1 d . . . . .
C5 C 0.87391(11) -0.22230(13) 0.56112(11) 0.0217(3) Uani 1 1 d . . . . .
H5 H 0.8704 -0.1541 0.5856 0.026 Uiso 1 1 calc R U . . .
C6 C 0.88219(11) -0.30758(13) 0.62187(11) 0.0221(3) Uani 1 1 d . . . . .
C7 C 0.88612(13) -0.28374(14) 0.72471(12) 0.0273(4) Uani 1 1 d . . . . .
H7 H 0.9186 -0.3414 0.7676 0.033 Uiso 1 1 calc R U . . .
C8 C 0.90568(15) -0.15905(16) 0.83559(13) 0.0346(4) Uani 1 1 d . . . . .
H8A H 0.9058 -0.0823 0.8438 0.041 Uiso 1 1 calc R U . . .
H8B H 0.9490 -0.1909 0.8930 0.041 Uiso 1 1 calc R U . . .
C9 C 0.80505(15) -0.20297(16) 0.81644(14) 0.0371(5) Uani 1 1 d . . . . .
H9A H 0.7984 -0.2454 0.8707 0.045 Uiso 1 1 calc R U . . .
H9B H 0.7570 -0.1461 0.8048 0.045 Uiso 1 1 calc R U . . .
C10 C 0.85595(11) -0.14424(12) 0.39650(11) 0.0208(3) Uani 1 1 d . . . . .
C11 C 0.85509(12) 0.05005(12) 0.38893(12) 0.0215(3) Uani 1 1 d . . . . .
C12 C 0.84125(13) 0.05832(13) 0.29129(12) 0.0263(4) Uani 1 1 d . . . . .
H12 H 0.8282 -0.0025 0.2528 0.032 Uiso 1 1 calc R U . . .
C13 C 0.84640(13) 0.15456(13) 0.25027(12) 0.0252(4) Uani 1 1 d . . . . .
H13 H 0.8377 0.1591 0.1838 0.030 Uiso 1 1 calc R U . . .
C14 C 0.86415(11) 0.24469(12) 0.30488(11) 0.0211(3) Uani 1 1 d . . . . .
C15 C 0.87330(11) 0.23741(13) 0.40155(11) 0.0216(3) Uani 1 1 d . . . . .
H15 H 0.8834 0.2991 0.4390 0.026 Uiso 1 1 calc R U . . .
C16 C 0.86794(11) 0.14185(13) 0.44447(11) 0.0213(3) Uani 1 1 d . . . . .
C17 C 0.87613(12) 0.14051(13) 0.54884(12) 0.0242(4) Uani 1 1 d . . . . .
H17 H 0.8883 0.2129 0.5750 0.029 Uiso 1 1 calc R U . . .
C18 C 0.93005(15) 0.06149(15) 0.68898(12) 0.0320(4) Uani 1 1 d . . . . .
H18A H 0.9550 0.1214 0.7312 0.038 Uiso 1 1 calc R U . . .
H18B H 0.9583 -0.0038 0.7208 0.038 Uiso 1 1 calc R U . . .
C19 C 0.82018(14) 0.05770(15) 0.66220(12) 0.0326(4) Uani 1 1 d . . . . .
H19A H 0.7971 -0.0149 0.6633 0.039 Uiso 1 1 calc R U . . .
H19B H 0.7951 0.1008 0.7061 0.039 Uiso 1 1 calc R U . . .
C20 C 0.87616(11) 0.34797(13) 0.26325(12) 0.0221(3) Uani 1 1 d . . . . .
C22 C 0.88789(12) 0.43627(12) 0.12517(12) 0.0241(4) Uani 1 1 d . . . . .
H22A H 0.9525 0.4645 0.1559 0.029 Uiso 1 1 calc R U . . .
H22B H 0.8397 0.4889 0.1307 0.029 Uiso 1 1 calc R U . . .
C23 C 0.87842(12) 0.41337(13) 0.02278(12) 0.0250(4) Uani 1 1 d . . . . .
H23A H 0.8209 0.3699 -0.0035 0.030 Uiso 1 1 calc R U . . .
H23B H 0.8704 0.4796 -0.0135 0.030 Uiso 1 1 calc R U . . .
C24 C 0.95518(14) 0.34460(14) -0.08484(12) 0.0282(4) Uani 1 1 d . . . . .
H24A H 0.9386 0.4114 -0.1195 0.034 Uiso 1 1 calc R U . . .
H24B H 0.9040 0.2935 -0.1126 0.034 Uiso 1 1 calc R U . . .
C25 C 1.04918(14) 0.30522(14) -0.09560(13) 0.0296(4) Uani 1 1 d . . . . .
H25A H 1.0513 0.3150 -0.1620 0.036 Uiso 1 1 calc R U . . .
H25B H 1.1024 0.3458 -0.0539 0.036 Uiso 1 1 calc R U . . .
C26 C 1.14965(13) 0.15904(14) -0.08082(12) 0.0274(4) Uani 1 1 d . . . . .
H26A H 1.2034 0.1923 -0.0330 0.033 Uiso 1 1 calc R U . . .
H26B H 1.1562 0.1760 -0.1446 0.033 Uiso 1 1 calc R U . . .
C27 C 1.15291(14) 0.04268(14) -0.06671(12) 0.0283(4) Uani 1 1 d . . . . .
H27A H 1.0911 0.0116 -0.1025 0.034 Uiso 1 1 calc R U . . .
H27B H 1.2040 0.0125 -0.0915 0.034 Uiso 1 1 calc R U . . .
C28 C 1.14540(14) -0.08615(15) 0.04506(14) 0.0343(4) Uani 1 1 d . . . . .
H28A H 1.1588 -0.1001 0.1132 0.051 Uiso 1 1 calc R U . . .
H28B H 1.0770 -0.0964 0.0146 0.051 Uiso 1 1 calc R U . . .
H28C H 1.1827 -0.1341 0.0172 0.051 Uiso 1 1 calc R U . . .
N1 N 0.89077(11) -0.50207(11) 0.63898(10) 0.0275(3) Uani 1 1 d . . . . .
N2 N 0.85729(11) -0.04657(11) 0.43469(11) 0.0226(3) Uani 1 1 d . . . . .
H1N H 0.8748(15) -0.0433(16) 0.4879(16) 0.027(6) Uiso 1 1 d . . . . .
O1 O 0.91754(10) -0.58296(10) 0.60942(10) 0.0368(3) Uani 1 1 d . . . . .
O2 O 0.86384(11) -0.49688(11) 0.71164(9) 0.0385(3) Uani 1 1 d . . . . .
O3 O 0.93371(9) -0.18704(10) 0.75192(9) 0.0310(3) Uani 1 1 d . . . . .
O4 O 0.79304(9) -0.26697(11) 0.73282(9) 0.0337(3) Uani 1 1 d . . . . .
O5 O 0.84142(9) -0.16138(9) 0.31182(8) 0.0262(3) Uani 1 1 d . . . . .
O6 O 0.79148(9) 0.10001(10) 0.56704(8) 0.0300(3) Uani 1 1 d . . . . .
O7 O 0.94990(9) 0.07341(10) 0.59899(8) 0.0281(3) Uani 1 1 d . . . . .
O8 O 0.88982(9) 0.42924(9) 0.30634(9) 0.0294(3) Uani 1 1 d . . . . .
O9 O 0.87303(9) 0.34005(9) 0.17084(8) 0.0246(3) Uani 1 1 d . . . . .
O10 O 0.96100(9) 0.36000(9) 0.01306(8) 0.0268(3) Uani 1 1 d . . . . .
O11 O 1.06070(9) 0.19778(9) -0.07137(9) 0.0274(3) Uani 1 1 d . . . . .
O12 O 1.17096(9) 0.01832(10) 0.03097(8) 0.0307(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.387(2) . ?
C1 C6 1.399(2) . ?
C1 N1 1.473(2) . ?
C2 C3 1.380(2) . ?
C3 C4 1.398(2) . ?
C4 C5 1.393(2) . ?
C4 C10 1.504(2) . ?
C5 C6 1.393(2) . ?
C6 C7 1.524(2) . ?
C7 O4 1.405(2) . ?
C7 O3 1.420(2) . ?
C8 O3 1.440(2) . ?
C8 C9 1.518(3) . ?
C9 O4 1.445(2) . ?
C10 O5 1.2208(19) . ?
C10 N2 1.368(2) . ?
C11 C12 1.394(2) . ?
C11 N2 1.403(2) . ?
C11 C16 1.413(2) . ?
C12 C13 1.382(2) . ?
C13 C14 1.388(2) . ?
C14 C15 1.390(2) . ?
C14 C20 1.487(2) . ?
C15 C16 1.388(2) . ?
C16 C17 1.502(2) . ?
C17 O7 1.412(2) . ?
C17 O6 1.425(2) . ?
C18 O7 1.434(2) . ?
C18 C19 1.535(3) . ?
C19 O6 1.447(2) . ?
C20 O8 1.205(2) . ?
C20 O9 1.3470(19) . ?
C22 O9 1.4463(19) . ?
C22 C23 1.498(2) . ?
C23 O10 1.421(2) . ?
C24 O10 1.428(2) . ?
C24 C25 1.503(3) . ?
C25 O11 1.419(2) . ?
C26 O11 1.425(2) . ?
C26 C27 1.503(2) . ?
C27 O12 1.418(2) . ?
C28 O12 1.418(2) . ?
N1 O1 1.2263(19) . ?
N1 O2 1.2334(19) . ?

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 C1 C6 122.09(15) . . ?
C2 C1 N1 116.69(14) . . ?
C6 C1 N1 121.21(15) . . ?
C3 C2 C1 119.81(15) . . ?
C2 C3 C4 119.99(15) . . ?
C5 C4 C3 119.01(15) . . ?
C5 C4 C10 124.00(14) . . ?
C3 C4 C10 116.99(14) . . ?
C6 C5 C4 122.30(15) . . ?
C5 C6 C1 116.70(15) . . ?
C5 C6 C7 116.66(15) . . ?
C1 C6 C7 126.62(15) . . ?
O4 C7 O3 104.35(14) . . ?
O4 C7 C6 109.81(14) . . ?
O3 C7 C6 109.61(14) . . ?
O3 C8 C9 103.48(14) . . ?
O4 C9 C8 104.64(15) . . ?
O5 C10 N2 124.03(15) . . ?
O5 C10 C4 120.18(14) . . ?
N2 C10 C4 115.76(14) . . ?
C12 C11 N2 122.40(15) . . ?
C12 C11 C16 119.19(15) . . ?
N2 C11 C16 118.41(14) . . ?
C13 C12 C11 120.33(15) . . ?
C12 C13 C14 120.92(15) . . ?
C13 C14 C15 118.90(15) . . ?
C13 C14 C20 121.80(15) . . ?
C15 C14 C20 119.28(14) . . ?
C16 C15 C14 121.33(15) . . ?
C15 C16 C11 119.15(15) . . ?
C15 C16 C17 118.26(14) . . ?
C11 C16 C17 122.59(15) . . ?
O7 C17 O6 104.53(13) . . ?
O7 C17 C16 111.96(13) . . ?
O6 C17 C16 111.35(13) . . ?
O7 C18 C19 103.02(14) . . ?
O6 C19 C18 103.79(14) . . ?
O8 C20 O9 123.19(15) . . ?
O8 C20 C14 125.02(15) . . ?
O9 C20 C14 111.76(14) . . ?
O9 C22 C23 108.24(13) . . ?
O10 C23 C22 110.30(13) . . ?
O10 C24 C25 110.31(14) . . ?
O11 C25 C24 110.29(14) . . ?
O11 C26 C27 109.07(14) . . ?
O12 C27 C26 110.30(14) . . ?
O1 N1 O2 123.86(15) . . ?
O1 N1 C1 118.00(14) . . ?
O2 N1 C1 118.10(14) . . ?
C10 N2 C11 127.89(14) . . ?
C7 O3 C8 103.11(13) . . ?
C7 O4 C9 105.30(14) . . ?
C17 O6 C19 106.39(13) . . ?
C17 O7 C18 103.21(13) . . ?
C20 O9 C22 115.69(12) . . ?
C23 O10 C24 110.41(13) . . ?
C25 O11 C26 111.13(13) . . ?
C27 O12 C28 111.80(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1N O6 0.75(2) 2.64(2) 3.0363(19) 115.5(18) .
N2 H1N O7 0.75(2) 2.26(2) 2.8620(19) 138(2) .

_refine_diff_density_max         0.523
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.057



####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1487437'
_audit_update_record             
;
2016-06-23 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;

_chemical_compound_source        'Nathalie Busschaert'
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H56 N4 O10'
_chemical_formula_sum            'C38 H56 N4 O10'
_chemical_formula_weight         728.86

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

_space_group_crystal_system      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                   10.0905(6)
_cell_length_b                   10.9163(6)
_cell_length_c                   18.1284(10)
_cell_angle_alpha                96.7110(10)
_cell_angle_beta                 93.4450(10)
_cell_angle_gamma                101.6850(10)
_cell_volume                     1934.86(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9987
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      25.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33355
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.922
_diffrn_reflns_theta_max         25.054
_diffrn_reflns_theta_full        25.054
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6827
_reflns_number_gt                4771
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Significant disorder is present in the appending oligoethyleneglycol chains. Various restraints were used to model the disorder
;
_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   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6827
_refine_ls_number_parameters     564
_refine_ls_number_restraints     99
_refine_ls_R_factor_all          0.1308
_refine_ls_R_factor_gt           0.1036
_refine_ls_wR_factor_ref         0.3546
_refine_ls_wR_factor_gt          0.3158
_refine_ls_goodness_of_fit_ref   1.464
_refine_ls_restrained_S_all      1.526
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.005

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 0.5206(6) -0.6613(5) 0.9238(3) 0.1128(13) Uani 0.43321(9) 1 d D U P A 1
O2 O 0.3290(4) -0.5523(4) 0.8563(3) 0.0995(9) Uani 0.43321(9) 1 d D U P A 1
O3 O 0.2084(4) -0.2852(3) 0.8181(2) 0.0665(5) Uani 0.43321(9) 1 d D . P A 1
O4 O 0.1380(4) 0.0179(3) 0.8610(2) 0.0665(5) Uani 0.43321(9) 1 d D . P A 1
C1 C 0.5309(9) -0.7417(7) 0.9775(4) 0.1128(13) Uani 0.43321(9) 1 d D . P A 1
H1A H 0.6084 -0.7034 1.0139 0.169 Uiso 0.43321(9) 1 calc R U P A 1
H1B H 0.5443 -0.8228 0.9533 0.169 Uiso 0.43321(9) 1 calc R U P A 1
H1C H 0.4474 -0.7551 1.0031 0.169 Uiso 0.43321(9) 1 calc R U P A 1
C2 C 0.4318(7) -0.7262(5) 0.8613(3) 0.0995(9) Uani 0.43321(9) 1 d D . P A 1
H2A H 0.3454 -0.7710 0.8776 0.119 Uiso 0.43321(9) 1 calc R U P A 1
H2B H 0.4743 -0.7885 0.8326 0.119 Uiso 0.43321(9) 1 calc R U P A 1
C3 C 0.4062(6) -0.6253(5) 0.8137(3) 0.0995(9) Uani 0.43321(9) 1 d D . P A 1
H3A H 0.4932 -0.5719 0.8036 0.119 Uiso 0.43321(9) 1 calc R U P A 1
H3B H 0.3551 -0.6647 0.7656 0.119 Uiso 0.43321(9) 1 calc R U P A 1
C4 C 0.2795(5) -0.4777(4) 0.8123(3) 0.0665(5) Uani 0.43321(9) 1 d D U P A 1
H4A H 0.2204 -0.5310 0.7701 0.080 Uiso 0.43321(9) 1 calc R U P A 1
H4B H 0.3558 -0.4240 0.7916 0.080 Uiso 0.43321(9) 1 calc R U P A 1
C5 C 0.2011(5) -0.3968(4) 0.8535(3) 0.0665(5) Uani 0.43321(9) 1 d D . P A 1
H5A H 0.1053 -0.4419 0.8527 0.080 Uiso 0.43321(9) 1 calc R U P A 1
H5B H 0.2393 -0.3743 0.9060 0.080 Uiso 0.43321(9) 1 calc R U P A 1
C6 C 0.1749(6) -0.1852(4) 0.8640(3) 0.0665(5) Uani 0.43321(9) 1 d D . P A 1
H6A H 0.2465 -0.1555 0.9057 0.080 Uiso 0.43321(9) 1 calc R U P A 1
H6B H 0.0886 -0.2165 0.8856 0.080 Uiso 0.43321(9) 1 calc R U P A 1
C7 C 0.1600(6) -0.0768(4) 0.8236(3) 0.0665(5) Uani 0.43321(9) 1 d D . P A 1
O1A O 0.4985(9) -0.5890(6) 0.9162(3) 0.1128(13) Uani 0.29422(9) 1 d D . P A 2
O2A O 0.4129(5) -0.4510(5) 0.8193(3) 0.0995(9) Uani 0.29422(9) 1 d D . P A 2
O3A O 0.2845(5) -0.2402(4) 0.8363(3) 0.0665(5) Uani 0.29422(9) 1 d D . P A 2
O4A O 0.2090(6) 0.0663(4) 0.8669(3) 0.0665(5) Uani 0.29422(9) 1 d D . P A 2
C1A C 0.4933(14) -0.6816(8) 0.9648(4) 0.1128(13) Uani 0.29422(9) 1 d D . P A 2
H1D H 0.4902 -0.6428 1.0161 0.169 Uiso 0.29422(9) 1 calc R U P A 2
H1E H 0.5742 -0.7181 0.9616 0.169 Uiso 0.29422(9) 1 calc R U P A 2
H1F H 0.4118 -0.7482 0.9505 0.169 Uiso 0.29422(9) 1 calc R U P A 2
C2A C 0.4533(11) -0.6540(6) 0.8417(3) 0.0995(9) Uani 0.29422(9) 1 d D . P A 2
H2C H 0.3560 -0.6959 0.8381 0.119 Uiso 0.29422(9) 1 calc R U P A 2
H2D H 0.5074 -0.7178 0.8272 0.119 Uiso 0.29422(9) 1 calc R U P A 2
C3A C 0.4770(8) -0.5485(6) 0.7938(4) 0.0995(9) Uani 0.29422(9) 1 d D . P A 2
H3C H 0.5758 -0.5144 0.7944 0.119 Uiso 0.29422(9) 1 calc R U P A 2
H3D H 0.4417 -0.5822 0.7417 0.119 Uiso 0.29422(9) 1 calc R U P A 2
C4A C 0.3133(6) -0.4653(5) 0.8669(4) 0.0665(5) Uani 0.29422(9) 1 d D . P A 2
H4C H 0.3529 -0.4706 0.9174 0.080 Uiso 0.29422(9) 1 calc R U P A 2
H4D H 0.2457 -0.5444 0.8499 0.080 Uiso 0.29422(9) 1 calc R U P A 2
C5A C 0.2451(7) -0.3545(4) 0.8693(4) 0.0665(5) Uani 0.29422(9) 1 d D . P A 2
H5C H 0.1500 -0.3904 0.8491 0.080 Uiso 0.29422(9) 1 calc R U P A 2
H5D H 0.2412 -0.3265 0.9230 0.080 Uiso 0.29422(9) 1 calc R U P A 2
C6A C 0.2672(7) -0.1295(4) 0.8775(3) 0.0665(5) Uani 0.29422(9) 1 d D . P A 2
H6C H 0.3544 -0.0889 0.9065 0.080 Uiso 0.29422(9) 1 calc R U P A 2
H6D H 0.1997 -0.1525 0.9136 0.080 Uiso 0.29422(9) 1 calc R U P A 2
C7A C 0.2227(7) -0.0346(4) 0.8346(3) 0.0665(5) Uani 0.29422(9) 1 d D . P A 2
O1B O 0.5401(8) -0.6973(6) 0.8797(5) 0.1128(13) Uani 0.27257(9) 1 d D . P A 3
O2B O 0.2698(5) -0.5984(5) 0.8212(4) 0.0995(9) Uani 0.27257(9) 1 d D . P A 3
O3B O 0.2069(6) -0.2884(4) 0.8199(3) 0.0665(5) Uani 0.27257(9) 1 d D . P A 3
O4B O 0.0973(5) 0.0010(5) 0.8504(3) 0.0665(5) Uani 0.27257(9) 1 d D . P A 3
C1B C 0.4878(14) -0.8194(7) 0.8960(7) 0.1128(13) Uani 0.27257(9) 1 d D . P A 3
H1G H 0.5604 -0.8520 0.9202 0.169 Uiso 0.27257(9) 1 calc R U P A 3
H1H H 0.4508 -0.8747 0.8497 0.169 Uiso 0.27257(9) 1 calc R U P A 3
H1I H 0.4154 -0.8167 0.9296 0.169 Uiso 0.27257(9) 1 calc R U P A 3
C2B C 0.5003(7) -0.6434(7) 0.8375(6) 0.0995(9) Uani 0.27257(9) 1 d D . P A 3
H2E H 0.4564 -0.7061 0.7946 0.119 Uiso 0.27257(9) 1 calc R U P A 3
H2F H 0.5803 -0.5904 0.8195 0.119 Uiso 0.27257(9) 1 calc R U P A 3
C3B C 0.4027(6) -0.5595(7) 0.8555(6) 0.0995(9) Uani 0.27257(9) 1 d D . P A 3
H3E H 0.3974 -0.5496 0.9102 0.119 Uiso 0.27257(9) 1 calc R U P A 3
H3F H 0.4415 -0.4752 0.8419 0.119 Uiso 0.27257(9) 1 calc R U P A 3
C4B C 0.2307(8) -0.4940(5) 0.7940(4) 0.0665(5) Uani 0.27257(9) 1 d D . P A 3
H4E H 0.1352 -0.5182 0.7723 0.080 Uiso 0.27257(9) 1 calc R U P A 3
H4F H 0.2886 -0.4661 0.7544 0.080 Uiso 0.27257(9) 1 calc R U P A 3
C5B C 0.2451(8) -0.3894(5) 0.8562(4) 0.0665(5) Uani 0.27257(9) 1 d D . P A 3
H5E H 0.1837 -0.4137 0.8951 0.080 Uiso 0.27257(9) 1 calc R U P A 3
H5F H 0.3398 -0.3644 0.8791 0.080 Uiso 0.27257(9) 1 calc R U P A 3
C6B C 0.1780(8) -0.1873(4) 0.8649(3) 0.0665(5) Uani 0.27257(9) 1 d D . P A 3
H6E H 0.2543 -0.1548 0.9037 0.080 Uiso 0.27257(9) 1 calc R U P A 3
H6F H 0.0960 -0.2177 0.8904 0.080 Uiso 0.27257(9) 1 calc R U P A 3
C7B C 0.1549(7) -0.0817(4) 0.8243(4) 0.0665(5) Uani 0.27257(9) 1 d D . P A 3
C8 C 0.1703(2) -0.0021(2) 0.70062(12) 0.0547(5) Uani 1 1 d . . . . .
C9 C 0.17650(19) -0.04420(18) 0.62440(12) 0.0511(5) Uani 1 1 d . . . . .
C10 C 0.1544(2) 0.03343(19) 0.57121(12) 0.0525(5) Uani 1 1 d . . . . .
H10 H 0.1584 0.0045 0.5201 0.063 Uiso 1 1 calc R U . . .
C11 C 0.1264(2) 0.15215(18) 0.59074(11) 0.0523(5) Uani 1 1 d . . . . .
C12 C 0.1198(2) 0.1913(2) 0.66598(12) 0.0556(5) Uani 1 1 d . . . . .
H12 H 0.0993 0.2715 0.6803 0.067 Uiso 1 1 calc R U . . .
C13 C 0.1420(2) 0.1179(2) 0.72033(12) 0.0592(6) Uani 1 1 d . . . . .
H13 H 0.1381 0.1483 0.7713 0.071 Uiso 1 1 calc R U . . .
C14 C 0.2007(2) -0.16962(19) 0.59664(12) 0.0534(5) Uani 1 1 d . . . . .
H14 H 0.1932 -0.1935 0.5442 0.064 Uiso 1 1 calc R U . . .
C15 C 0.2490(2) -0.3683(2) 0.60283(14) 0.0616(6) Uani 1 1 d . . . . .
H15A H 0.2282 -0.3751 0.5482 0.074 Uiso 1 1 calc R U . . .
H15B H 0.1848 -0.4366 0.6215 0.074 Uiso 1 1 calc R U . . .
C16 C 0.3948(2) -0.3849(2) 0.61930(13) 0.0614(6) Uani 1 1 d . . . . .
H16 H 0.4193 -0.3662 0.6743 0.074 Uiso 1 1 calc R U . . .
C17 C 0.4040(2) -0.5209(2) 0.59347(16) 0.0732(7) Uani 1 1 d . . . . .
H17A H 0.3402 -0.5783 0.6189 0.110 Uiso 1 1 calc R U . . .
H17B H 0.3810 -0.5400 0.5395 0.110 Uiso 1 1 calc R U . . .
H17C H 0.4966 -0.5316 0.6054 0.110 Uiso 1 1 calc R U . . .
C18 C 0.4925(2) -0.2942(2) 0.58071(16) 0.0730(7) Uani 1 1 d . . . . .
H18A H 0.4854 -0.2075 0.5979 0.109 Uiso 1 1 calc R U . . .
H18B H 0.5855 -0.3041 0.5926 0.109 Uiso 1 1 calc R U . . .
H18C H 0.4699 -0.3124 0.5267 0.109 Uiso 1 1 calc R U . . .
C19 C 0.0987(2) 0.23885(19) 0.53616(12) 0.0547(5) Uani 1 1 d . . . . .
C20 C 0.1283(2) 0.27847(19) 0.40562(12) 0.0536(5) Uani 1 1 d . . . . .
C21 C 0.1468(2) 0.21692(19) 0.33438(12) 0.0537(5) Uani 1 1 d . . . . .
C22 C 0.1424(2) 0.2816(2) 0.27299(13) 0.0632(6) Uani 1 1 d . . . . .
H22 H 0.1535 0.2409 0.2252 0.076 Uiso 1 1 calc R U . . .
C23 C 0.1219(3) 0.4049(2) 0.27987(14) 0.0669(6) Uani 1 1 d . . . . .
C24 C 0.1041(2) 0.4638(2) 0.34998(13) 0.0634(6) Uani 1 1 d . . . . .
H24 H 0.0904 0.5479 0.3552 0.076 Uiso 1 1 calc R U . . .
C25 C 0.1061(2) 0.40129(19) 0.41196(13) 0.0572(5) Uani 1 1 d . . . . .
H25 H 0.0924 0.4422 0.4592 0.069 Uiso 1 1 calc R U . . .
C26 C 0.1714(2) 0.0885(2) 0.32142(12) 0.0554(5) Uani 1 1 d . . . . .
H26 H 0.1670 0.0503 0.2712 0.067 Uiso 1 1 calc R U . . .
C27 C 0.2249(2) -0.10099(19) 0.34986(13) 0.0599(6) Uani 1 1 d . . . . .
H27A H 0.1939 -0.1281 0.2965 0.072 Uiso 1 1 calc R U . . .
H27B H 0.1730 -0.1624 0.3792 0.072 Uiso 1 1 calc R U . . .
C28 C 0.3766(2) -0.0999(2) 0.36227(14) 0.0672(6) Uani 1 1 d . . . . .
H28 H 0.4161 -0.0567 0.4128 0.081 Uiso 0.567(5) 1 d R U P B 1
H28' H 0.4285 -0.0448 0.3289 0.081 Uiso 0.433(5) 1 d R U P B 2
C29 C 0.4018(4) -0.2302(3) 0.3480(2) 0.1175(12) Uani 1 1 d . . . . .
H29A H 0.3734 -0.2649 0.2958 0.176 Uiso 1 1 calc R U . . .
H29B H 0.3498 -0.2838 0.3806 0.176 Uiso 1 1 calc R U . . .
H29C H 0.4989 -0.2277 0.3583 0.176 Uiso 1 1 calc R U . . .
C30 C 0.4450(5) -0.0386(5) 0.3017(3) 0.0890(16) Uani 0.567(5) 1 d . . P B 1
H30A H 0.5435 -0.0297 0.3105 0.133 Uiso 0.567(5) 1 calc R U P B 1
H30B H 0.4238 0.0449 0.3008 0.133 Uiso 0.567(5) 1 calc R U P B 1
H30C H 0.4129 -0.0907 0.2537 0.133 Uiso 0.567(5) 1 calc R U P B 1
C30' C 0.4379(5) -0.0570(5) 0.4457(3) 0.0612(14) Uani 0.433(5) 1 d . . P B -2
H30D H 0.3914 -0.1153 0.4777 0.092 Uiso 0.433(5) 1 calc R U P B -2
H30E H 0.4253 0.0284 0.4618 0.092 Uiso 0.433(5) 1 calc R U P B -2
H30F H 0.5351 -0.0576 0.4493 0.092 Uiso 0.433(5) 1 calc R U P B -2
C31 C 0.1230(3) 0.4794(2) 0.21648(14) 0.0767(7) Uani 1 1 d . . . . .
N1 N 0.1910(2) -0.08205(18) 0.75236(10) 0.0639(5) Uani 1 1 d . . . . .
H1N H 0.210(3) -0.137(3) 0.7350(16) 0.087(9) Uiso 1 1 d . . . . .
N2 N 0.13735(17) 0.21331(16) 0.46665(10) 0.0524(4) Uani 1 1 d . . . . .
H2N H 0.151(2) 0.162(2) 0.4609(12) 0.056(6) Uiso 1 1 d . . . . .
N3 N 0.23060(17) -0.24726(16) 0.63767(10) 0.0565(5) Uani 1 1 d . . . . .
N4 N 0.19803(18) 0.02478(16) 0.37243(10) 0.0549(4) Uani 1 1 d . . . . .
O5 O 0.04567(16) 0.32818(13) 0.55486(9) 0.0628(4) Uani 1 1 d . . . . .
O6 O 0.1102(3) 0.58745(17) 0.22122(11) 0.0978(7) Uani 1 1 d . . . . .
O7 O 0.14014(19) 0.41300(16) 0.15134(9) 0.0803(5) Uani 1 1 d D . . . .
O8 O -0.0015(3) 0.3249(3) -0.00298(18) 0.0652(6) Uani 0.48533(9) 1 d D . P C 1
O9 O -0.2055(4) 0.1174(3) -0.0461(2) 0.0814(8) Uani 0.48533(9) 1 d D . P C 1
O10 O -0.3300(5) -0.0975(5) -0.1671(2) 0.1064(10) Uani 0.48533(9) 1 d D . P C 1
C32 C 0.1666(6) 0.4785(5) 0.0866(2) 0.0739(6) Uani 0.48533(9) 1 d D . P C 1
H32A H 0.2627 0.5242 0.0906 0.089 Uiso 0.48533(9) 1 calc R U P C 1
H32B H 0.1080 0.5407 0.0838 0.089 Uiso 0.48533(9) 1 calc R U P C 1
C33 C 0.1373(5) 0.3827(5) 0.0180(3) 0.0739(6) Uani 0.48533(9) 1 d D . P C 1
H33A H 0.1747 0.4242 -0.0243 0.089 Uiso 0.48533(9) 1 calc R U P C 1
H33B H 0.1873 0.3153 0.0256 0.089 Uiso 0.48533(9) 1 calc R U P C 1
C34 C 0.0077(5) 0.2413(6) -0.0692(3) 0.0867(9) Uani 0.48533(9) 1 d D . P C 1
H34A H 0.0547 0.1740 -0.0570 0.104 Uiso 0.48533(9) 1 calc R U P C 1
H34B H 0.0576 0.2882 -0.1061 0.104 Uiso 0.48533(9) 1 calc R U P C 1
C35 C -0.1385(5) 0.1862(5) -0.0989(3) 0.0867(9) Uani 0.48533(9) 1 d D . P C 1
H35A H -0.1849 0.2549 -0.1091 0.104 Uiso 0.48533(9) 1 calc R U P C 1
H35B H -0.1411 0.1300 -0.1462 0.104 Uiso 0.48533(9) 1 calc R U P C 1
C36 C -0.2039(6) -0.0151(5) -0.0505(4) 0.0981(10) Uani 0.48533(9) 1 d D . P C 1
H36A H -0.1912 -0.0362 0.0007 0.118 Uiso 0.48533(9) 1 calc R U P C 1
H36B H -0.1245 -0.0306 -0.0768 0.118 Uiso 0.48533(9) 1 calc R U P C 1
C37 C -0.3306(6) -0.1039(6) -0.0900(3) 0.0981(10) Uani 0.48533(9) 1 d D . P C 1
H37A H -0.3316 -0.1913 -0.0800 0.118 Uiso 0.48533(9) 1 calc R U P C 1
H37B H -0.4128 -0.0790 -0.0713 0.118 Uiso 0.48533(9) 1 calc R U P C 1
C38 C -0.4518(6) -0.1732(7) -0.2078(3) 0.1064(10) Uani 0.48533(9) 1 d D . P C 1
H38A H -0.4388 -0.2593 -0.2216 0.160 Uiso 0.48533(9) 1 calc R U P C 1
H38B H -0.4715 -0.1366 -0.2530 0.160 Uiso 0.48533(9) 1 calc R U P C 1
H38C H -0.5279 -0.1754 -0.1765 0.160 Uiso 0.48533(9) 1 calc R U P C 1
O8A O 0.0449(6) 0.3297(6) 0.0066(3) 0.0652(6) Uani 0.24338(9) 1 d D . P C 2
O9A O -0.1253(8) 0.0891(5) -0.0327(3) 0.0814(8) Uani 0.24338(9) 1 d D . P C 2
O10A O -0.2822(7) -0.2071(6) -0.1278(4) 0.1064(10) Uani 0.24338(9) 1 d D . P C
2
C32A C 0.1274(9) 0.4817(7) 0.0886(3) 0.0739(6) Uani 0.24338(9) 1 d D . P C 2
H32C H 0.1834 0.5685 0.0985 0.089 Uiso 0.24338(9) 1 calc R U P C 2
H32D H 0.0316 0.4857 0.0760 0.089 Uiso 0.24338(9) 1 calc R U P C 2
C33A C 0.1800(6) 0.4028(8) 0.0273(5) 0.0739(6) Uani 0.24338(9) 1 d D . P C 2
H33C H 0.2186 0.4514 -0.0121 0.089 Uiso 0.24338(9) 1 calc R U P C 2
H33D H 0.2440 0.3533 0.0459 0.089 Uiso 0.24338(9) 1 calc R U P C 2
C34A C 0.0391(8) 0.2519(8) -0.0637(4) 0.0867(9) Uani 0.24338(9) 1 d D . P C 2
H34C H 0.1075 0.1989 -0.0598 0.104 Uiso 0.24338(9) 1 calc R U P C 2
H34D H 0.0657 0.3076 -0.1021 0.104 Uiso 0.24338(9) 1 calc R U P C 2
C35A C -0.0974(9) 0.1662(8) -0.0904(4) 0.0867(9) Uani 0.24338(9) 1 d D . P C 2
H35C H -0.1682 0.2159 -0.0969 0.104 Uiso 0.24338(9) 1 calc R U P C 2
H35D H -0.0925 0.1142 -0.1383 0.104 Uiso 0.24338(9) 1 calc R U P C 2
C36A C -0.1628(8) -0.0364(7) -0.0674(6) 0.0981(10) Uani 0.24338(9) 1 d D . P C
2
H36C H -0.1638 -0.0921 -0.0280 0.118 Uiso 0.24338(9) 1 calc R U P C 2
H36D H -0.0904 -0.0522 -0.0995 0.118 Uiso 0.24338(9) 1 calc R U P C 2
C37A C -0.2997(8) -0.0782(7) -0.1153(6) 0.0981(10) Uani 0.24338(9) 1 d D . P C
2
H37C H -0.3788 -0.0684 -0.0872 0.118 Uiso 0.24338(9) 1 calc R U P C 2
H37D H -0.3018 -0.0381 -0.1615 0.118 Uiso 0.24338(9) 1 calc R U P C 2
C38A C -0.3996(9) -0.2653(13) -0.1754(6) 0.1064(10) Uani 0.24338(9) 1 d D . P C
2
H38D H -0.4666 -0.2117 -0.1720 0.160 Uiso 0.24338(9) 1 calc R U P C 2
H38E H -0.4383 -0.3475 -0.1603 0.160 Uiso 0.24338(9) 1 calc R U P C 2
H38F H -0.3753 -0.2772 -0.2269 0.160 Uiso 0.24338(9) 1 calc R U P C 2
O8B O 0.0211(5) 0.3199(5) -0.0059(3) 0.0652(6) Uani 0.27127(9) 1 d D . P C 3
O9B O -0.2372(7) 0.0909(5) -0.0469(4) 0.0814(8) Uani 0.27127(9) 1 d D . P C 3
O10B O -0.3373(6) -0.0642(8) -0.1572(4) 0.1064(10) Uani 0.27127(9) 1 d D . P C
3
C32B C 0.1436(10) 0.4864(7) 0.0898(3) 0.0739(6) Uani 0.27127(9) 1 d D . P C 3
H32E H 0.2246 0.5564 0.0981 0.089 Uiso 0.27127(9) 1 calc R U P C 3
H32F H 0.0620 0.5236 0.0876 0.089 Uiso 0.27127(9) 1 calc R U P C 3
C33B C 0.1481(7) 0.4061(8) 0.0168(4) 0.0739(6) Uani 0.27127(9) 1 d D . P C 3
H33E H 0.1707 0.4614 -0.0222 0.089 Uiso 0.27127(9) 1 calc R U P C 3
H33F H 0.2207 0.3579 0.0219 0.089 Uiso 0.27127(9) 1 calc R U P C 3
C34B C -0.0180(7) 0.2368(9) -0.0750(4) 0.0867(9) Uani 0.27127(9) 1 d D . P C 3
H34E H 0.0301 0.1663 -0.0750 0.104 Uiso 0.27127(9) 1 calc R U P C 3
H34F H 0.0124 0.2839 -0.1166 0.104 Uiso 0.27127(9) 1 calc R U P C 3
C35B C -0.1704(7) 0.1821(8) -0.0897(5) 0.0867(9) Uani 0.27127(9) 1 d D . P C 3
H35E H -0.2167 0.2540 -0.0843 0.104 Uiso 0.27127(9) 1 calc R U P C 3
H35F H -0.1874 0.1442 -0.1426 0.104 Uiso 0.27127(9) 1 calc R U P C 3
C36B C -0.1830(8) -0.0215(6) -0.0531(7) 0.0981(10) Uani 0.27127(9) 1 d D . P C
3
H36E H -0.1562 -0.0427 -0.0034 0.118 Uiso 0.27127(9) 1 calc R U P C 3
H36F H -0.1040 -0.0132 -0.0833 0.118 Uiso 0.27127(9) 1 calc R U P C 3
C37B C -0.3037(8) -0.1184(8) -0.0921(4) 0.0981(10) Uani 0.27127(9) 1 d D . P C
3
H37E H -0.2789 -0.2008 -0.1058 0.118 Uiso 0.27127(9) 1 calc R U P C 3
H37F H -0.3804 -0.1301 -0.0603 0.118 Uiso 0.27127(9) 1 calc R U P C 3
C38B C -0.4805(7) -0.0973(13) -0.1791(6) 0.1064(10) Uani 0.27127(9) 1 d D . P C
3
H38G H -0.5194 -0.1780 -0.1622 0.160 Uiso 0.27127(9) 1 calc R U P C 3
H38H H -0.4955 -0.1051 -0.2335 0.160 Uiso 0.27127(9) 1 calc R U P C 3
H38I H -0.5242 -0.0316 -0.1564 0.160 Uiso 0.27127(9) 1 calc R U P C 3


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.398(7) . ?
O1 C2 1.422(6) . ?
O2 C4 1.348(6) . ?
O2 C3 1.420(6) . ?
O3 C6 1.403(5) . ?
O3 C5 1.433(5) . ?
O4 C7 1.235(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.528(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.470(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.490(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N1 1.345(5) . ?
O1A C1A 1.412(8) . ?
O1A C2A 1.451(7) . ?
O2A C4A 1.361(7) . ?
O2A C3A 1.401(7) . ?
O3A C6A 1.392(6) . ?
O3A C5A 1.441(6) . ?
O4A C7A 1.223(6) . ?
C1A H1D 0.9800 . ?
C1A H1E 0.9800 . ?
C1A H1F 0.9800 . ?
C2A C3A 1.512(8) . ?
C2A H2C 0.9900 . ?
C2A H2D 0.9900 . ?
C3A H3C 0.9900 . ?
C3A H3D 0.9900 . ?
C4A C5A 1.505(7) . ?
C4A H4C 0.9900 . ?
C4A H4D 0.9900 . ?
C5A H5C 0.9900 . ?
C5A H5D 0.9900 . ?
C6A C7A 1.487(6) . ?
C6A H6C 0.9900 . ?
C6A H6D 0.9900 . ?
C7A N1 1.513(6) . ?
O1B C2B 1.122(12) . ?
O1B C1B 1.402(8) . ?
O2B C3B 1.405(7) . ?
O2B C4B 1.411(7) . ?
O3B C6B 1.384(6) . ?
O3B C5B 1.452(7) . ?
O4B C7B 1.234(6) . ?
C1B H1G 0.9800 . ?
C1B H1H 0.9800 . ?
C1B H1I 0.9800 . ?
C2B C3B 1.499(8) . ?
C2B H2E 0.9900 . ?
C2B H2F 0.9900 . ?
C3B H3E 0.9900 . ?
C3B H3F 0.9900 . ?
C4B C5B 1.486(7) . ?
C4B H4E 0.9900 . ?
C4B H4F 0.9900 . ?
C5B H5E 0.9900 . ?
C5B H5F 0.9900 . ?
C6B C7B 1.488(5) . ?
C6B H6E 0.9900 . ?
C6B H6F 0.9900 . ?
C7B N1 1.374(7) . ?
C8 N1 1.388(3) . ?
C8 C13 1.407(3) . ?
C8 C9 1.414(3) . ?
C9 C10 1.393(3) . ?
C9 C14 1.475(3) . ?
C10 C11 1.392(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(3) . ?
C11 C19 1.499(3) . ?
C12 C13 1.377(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 N3 1.260(3) . ?
C14 H14 0.9500 . ?
C15 N3 1.448(3) . ?
C15 C16 1.534(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C18 1.514(3) . ?
C16 C17 1.526(3) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O5 1.228(3) . ?
C19 N2 1.356(3) . ?
C20 N2 1.392(3) . ?
C20 C25 1.396(3) . ?
C20 C21 1.425(3) . ?
C21 C22 1.389(3) . ?
C21 C26 1.467(3) . ?
C22 C23 1.395(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.394(3) . ?
C23 C31 1.483(4) . ?
C24 C25 1.382(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 N4 1.268(3) . ?
C26 H26 0.9500 . ?
C27 N4 1.469(3) . ?
C27 C28 1.531(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C30 1.486(6) . ?
C28 C29 1.491(4) . ?
C28 C30' 1.579(6) . ?
C28 H28 1.0000 . ?
C28 H28' 1.0000 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C30' H30D 0.9800 . ?
C30' H30E 0.9800 . ?
C30' H30F 0.9800 . ?
C31 O6 1.206(3) . ?
C31 O7 1.351(3) . ?
N1 H1N 0.71(3) . ?
N2 H2N 0.60(2) . ?
O7 C32B 1.445(6) . ?
O7 C32A 1.447(6) . ?
O7 C32 1.455(5) . ?
O8 C33 1.424(5) . ?
O8 C34 1.440(5) . ?
O9 C35 1.407(6) . ?
O9 C36 1.444(6) . ?
O10 C37 1.409(6) . ?
O10 C38 1.441(6) . ?
C32 C33 1.502(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.516(6) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.520(6) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
O8A C33A 1.437(7) . ?
O8A C34A 1.437(7) . ?
O9A C36A 1.406(7) . ?
O9A C35A 1.424(8) . ?
O10A C38A 1.413(8) . ?
O10A C37A 1.446(8) . ?
C32A C33A 1.514(8) . ?
C32A H32C 0.9900 . ?
C32A H32D 0.9900 . ?
C33A H33C 0.9900 . ?
C33A H33D 0.9900 . ?
C34A C35A 1.516(8) . ?
C34A H34C 0.9900 . ?
C34A H34D 0.9900 . ?
C35A H35C 0.9900 . ?
C35A H35D 0.9900 . ?
C36A C37A 1.543(8) . ?
C36A H36C 0.9900 . ?
C36A H36D 0.9900 . ?
C37A H37C 0.9900 . ?
C37A H37D 0.9900 . ?
C38A H38D 0.9800 . ?
C38A H38E 0.9800 . ?
C38A H38F 0.9800 . ?
O8B C33B 1.433(7) . ?
O8B C34B 1.442(7) . ?
O9B C35B 1.420(8) . ?
O9B C36B 1.437(8) . ?
O10B C37B 1.433(8) . ?
O10B C38B 1.435(7) . ?
C32B C33B 1.509(7) . ?
C32B H32E 0.9900 . ?
C32B H32F 0.9900 . ?
C33B H33E 0.9900 . ?
C33B H33F 0.9900 . ?
C34B C35B 1.528(7) . ?
C34B H34E 0.9900 . ?
C34B H34F 0.9900 . ?
C35B H35E 0.9900 . ?
C35B H35F 0.9900 . ?
C36B C37B 1.518(8) . ?
C36B H36E 0.9900 . ?
C36B H36F 0.9900 . ?
C37B H37E 0.9900 . ?
C37B H37F 0.9900 . ?
C38B H38G 0.9800 . ?
C38B H38H 0.9800 . ?
C38B H38I 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C2 110.5(5) . . ?
C4 O2 C3 108.8(4) . . ?
C6 O3 C5 113.0(4) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 106.1(5) . . ?
O1 C2 H2A 110.5 . . ?
C3 C2 H2A 110.5 . . ?
O1 C2 H2B 110.5 . . ?
C3 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
O2 C3 C2 105.5(5) . . ?
O2 C3 H3A 110.6 . . ?
C2 C3 H3A 110.6 . . ?
O2 C3 H3B 110.6 . . ?
C2 C3 H3B 110.6 . . ?
H3A C3 H3B 108.8 . . ?
O2 C4 C5 111.8(4) . . ?
O2 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
O2 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
O3 C5 C4 107.9(4) . . ?
O3 C5 H5A 110.1 . . ?
C4 C5 H5A 110.1 . . ?
O3 C5 H5B 110.1 . . ?
C4 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
O3 C6 C7 113.0(4) . . ?
O3 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
O3 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
O4 C7 N1 124.5(4) . . ?
O4 C7 C6 117.1(4) . . ?
N1 C7 C6 117.7(4) . . ?
C1A O1A C2A 107.5(6) . . ?
C4A O2A C3A 123.1(6) . . ?
C6A O3A C5A 116.4(5) . . ?
O1A C1A H1D 109.5 . . ?
O1A C1A H1E 109.5 . . ?
H1D C1A H1E 109.5 . . ?
O1A C1A H1F 109.5 . . ?
H1D C1A H1F 109.5 . . ?
H1E C1A H1F 109.5 . . ?
O1A C2A C3A 102.9(6) . . ?
O1A C2A H2C 111.2 . . ?
C3A C2A H2C 111.2 . . ?
O1A C2A H2D 111.2 . . ?
C3A C2A H2D 111.2 . . ?
H2C C2A H2D 109.1 . . ?
O2A C3A C2A 111.5(6) . . ?
O2A C3A H3C 109.3 . . ?
C2A C3A H3C 109.3 . . ?
O2A C3A H3D 109.3 . . ?
C2A C3A H3D 109.3 . . ?
H3C C3A H3D 108.0 . . ?
O2A C4A C5A 109.5(5) . . ?
O2A C4A H4C 109.8 . . ?
C5A C4A H4C 109.8 . . ?
O2A C4A H4D 109.8 . . ?
C5A C4A H4D 109.8 . . ?
H4C C4A H4D 108.2 . . ?
O3A C5A C4A 128.1(6) . . ?
O3A C5A H5C 105.3 . . ?
C4A C5A H5C 105.3 . . ?
O3A C5A H5D 105.3 . . ?
C4A C5A H5D 105.3 . . ?
H5C C5A H5D 106.0 . . ?
O3A C6A C7A 116.7(5) . . ?
O3A C6A H6C 108.1 . . ?
C7A C6A H6C 108.1 . . ?
O3A C6A H6D 108.1 . . ?
C7A C6A H6D 108.1 . . ?
H6C C6A H6D 107.3 . . ?
O4A C7A C6A 120.2(5) . . ?
O4A C7A N1 127.1(5) . . ?
C6A C7A N1 112.6(4) . . ?
C2B O1B C1B 129.5(9) . . ?
C3B O2B C4B 108.6(6) . . ?
C6B O3B C5B 117.6(5) . . ?
O1B C1B H1G 109.5 . . ?
O1B C1B H1H 109.5 . . ?
H1G C1B H1H 109.5 . . ?
O1B C1B H1I 109.5 . . ?
H1G C1B H1I 109.5 . . ?
H1H C1B H1I 109.5 . . ?
O1B C2B C3B 122.2(10) . . ?
O1B C2B H2E 106.8 . . ?
C3B C2B H2E 106.8 . . ?
O1B C2B H2F 106.8 . . ?
C3B C2B H2F 106.8 . . ?
H2E C2B H2F 106.6 . . ?
O2B C3B C2B 117.3(7) . . ?
O2B C3B H3E 108.0 . . ?
C2B C3B H3E 108.0 . . ?
O2B C3B H3F 108.0 . . ?
C2B C3B H3F 108.0 . . ?
H3E C3B H3F 107.2 . . ?
O2B C4B C5B 109.2(5) . . ?
O2B C4B H4E 109.8 . . ?
C5B C4B H4E 109.8 . . ?
O2B C4B H4F 109.8 . . ?
C5B C4B H4F 109.8 . . ?
H4E C4B H4F 108.3 . . ?
O3B C5B C4B 103.2(5) . . ?
O3B C5B H5E 111.1 . . ?
C4B C5B H5E 111.1 . . ?
O3B C5B H5F 111.1 . . ?
C4B C5B H5F 111.1 . . ?
H5E C5B H5F 109.1 . . ?
O3B C6B C7B 114.2(5) . . ?
O3B C6B H6E 108.7 . . ?
C7B C6B H6E 108.7 . . ?
O3B C6B H6F 108.7 . . ?
C7B C6B H6F 108.7 . . ?
H6E C6B H6F 107.6 . . ?
O4B C7B N1 118.8(5) . . ?
O4B C7B C6B 123.0(6) . . ?
N1 C7B C6B 118.0(5) . . ?
N1 C8 C13 123.20(19) . . ?
N1 C8 C9 118.23(19) . . ?
C13 C8 C9 118.6(2) . . ?
C10 C9 C8 119.44(19) . . ?
C10 C9 C14 116.93(18) . . ?
C8 C9 C14 123.60(19) . . ?
C11 C10 C9 121.97(19) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C12 C11 C10 117.7(2) . . ?
C12 C11 C19 117.78(18) . . ?
C10 C11 C19 124.54(19) . . ?
C13 C12 C11 122.2(2) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C12 C13 C8 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
N3 C14 C9 124.5(2) . . ?
N3 C14 H14 117.7 . . ?
C9 C14 H14 117.7 . . ?
N3 C15 C16 111.37(17) . . ?
N3 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
N3 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C18 C16 C17 110.5(2) . . ?
C18 C16 C15 110.1(2) . . ?
C17 C16 C15 109.79(18) . . ?
C18 C16 H16 108.8 . . ?
C17 C16 H16 108.8 . . ?
C15 C16 H16 108.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 N2 123.1(2) . . ?
O5 C19 C11 120.87(19) . . ?
N2 C19 C11 116.03(18) . . ?
N2 C20 C25 122.8(2) . . ?
N2 C20 C21 117.64(18) . . ?
C25 C20 C21 119.5(2) . . ?
C22 C21 C20 118.7(2) . . ?
C22 C21 C26 117.30(19) . . ?
C20 C21 C26 124.04(19) . . ?
C21 C22 C23 121.5(2) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
C24 C23 C22 119.1(2) . . ?
C24 C23 C31 117.6(2) . . ?
C22 C23 C31 123.3(2) . . ?
C25 C24 C23 120.7(2) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C20 120.5(2) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?
N4 C26 C21 124.67(19) . . ?
N4 C26 H26 117.7 . . ?
C21 C26 H26 117.7 . . ?
N4 C27 C28 110.90(17) . . ?
N4 C27 H27A 109.5 . . ?
C28 C27 H27A 109.5 . . ?
N4 C27 H27B 109.5 . . ?
C28 C27 H27B 109.5 . . ?
H27A C27 H27B 108.0 . . ?
C30 C28 C29 102.0(3) . . ?
C30 C28 C27 107.5(3) . . ?
C29 C28 C27 110.9(2) . . ?
C29 C28 C30' 102.1(3) . . ?
C27 C28 C30' 114.0(3) . . ?
C30 C28 H28 112.0 . . ?
C29 C28 H28 112.0 . . ?
C27 C28 H28 111.9 . . ?
C29 C28 H28' 110.1 . . ?
C27 C28 H28' 109.8 . . ?
C30' C28 H28' 109.7 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C30' H30D 109.5 . . ?
C28 C30' H30E 109.5 . . ?
H30D C30' H30E 109.5 . . ?
C28 C30' H30F 109.5 . . ?
H30D C30' H30F 109.5 . . ?
H30E C30' H30F 109.5 . . ?
O6 C31 O7 122.6(2) . . ?
O6 C31 C23 124.8(2) . . ?
O7 C31 C23 112.6(2) . . ?
C7 N1 C8 128.6(3) . . ?
C7B N1 C8 129.6(3) . . ?
C8 N1 C7A 121.8(2) . . ?
C7 N1 H1N 119(2) . . ?
C7B N1 H1N 118(2) . . ?
C8 N1 H1N 111(2) . . ?
C7A N1 H1N 123(2) . . ?
C19 N2 C20 128.95(19) . . ?
C19 N2 H2N 113(2) . . ?
C20 N2 H2N 117(2) . . ?
C14 N3 C15 118.63(19) . . ?
C26 N4 C27 117.81(18) . . ?
C31 O7 C32B 112.6(3) . . ?
C31 O7 C32A 112.3(3) . . ?
C31 O7 C32 119.2(3) . . ?
C33 O8 C34 102.0(4) . . ?
C35 O9 C36 118.0(5) . . ?
C37 O10 C38 111.8(5) . . ?
O7 C32 C33 108.5(4) . . ?
O7 C32 H32A 110.0 . . ?
C33 C32 H32A 110.0 . . ?
O7 C32 H32B 110.0 . . ?
C33 C32 H32B 110.0 . . ?
H32A C32 H32B 108.4 . . ?
O8 C33 C32 116.7(4) . . ?
O8 C33 H33A 108.1 . . ?
C32 C33 H33A 108.1 . . ?
O8 C33 H33B 108.1 . . ?
C32 C33 H33B 108.1 . . ?
H33A C33 H33B 107.3 . . ?
O8 C34 C35 104.7(4) . . ?
O8 C34 H34A 110.8 . . ?
C35 C34 H34A 110.8 . . ?
O8 C34 H34B 110.8 . . ?
C35 C34 H34B 110.8 . . ?
H34A C34 H34B 108.9 . . ?
O9 C35 C34 109.4(4) . . ?
O9 C35 H35A 109.8 . . ?
C34 C35 H35A 109.8 . . ?
O9 C35 H35B 109.8 . . ?
C34 C35 H35B 109.8 . . ?
H35A C35 H35B 108.2 . . ?
O9 C36 C37 115.1(5) . . ?
O9 C36 H36A 108.5 . . ?
C37 C36 H36A 108.5 . . ?
O9 C36 H36B 108.5 . . ?
C37 C36 H36B 108.5 . . ?
H36A C36 H36B 107.5 . . ?
O10 C37 C36 108.6(5) . . ?
O10 C37 H37A 110.0 . . ?
C36 C37 H37A 110.0 . . ?
O10 C37 H37B 110.0 . . ?
C36 C37 H37B 110.0 . . ?
H37A C37 H37B 108.3 . . ?
O10 C38 H38A 109.5 . . ?
O10 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O10 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C33A O8A C34A 110.7(6) . . ?
C36A O9A C35A 106.8(7) . . ?
C38A O10A C37A 101.3(8) . . ?
O7 C32A C33A 102.0(6) . . ?
O7 C32A H32C 111.4 . . ?
C33A C32A H32C 111.4 . . ?
O7 C32A H32D 111.4 . . ?
C33A C32A H32D 111.4 . . ?
H32C C32A H32D 109.2 . . ?
O8A C33A C32A 90.2(5) . . ?
O8A C33A H33C 113.6 . . ?
C32A C33A H33C 113.6 . . ?
O8A C33A H33D 113.6 . . ?
C32A C33A H33D 113.6 . . ?
H33C C33A H33D 110.9 . . ?
O8A C34A C35A 115.8(6) . . ?
O8A C34A H34C 108.3 . . ?
C35A C34A H34C 108.3 . . ?
O8A C34A H34D 108.3 . . ?
C35A C34A H34D 108.3 . . ?
H34C C34A H34D 107.4 . . ?
O9A C35A C34A 104.1(6) . . ?
O9A C35A H35C 110.9 . . ?
C34A C35A H35C 110.9 . . ?
O9A C35A H35D 110.9 . . ?
C34A C35A H35D 110.9 . . ?
H35C C35A H35D 109.0 . . ?
O9A C36A C37A 118.4(7) . . ?
O9A C36A H36C 107.7 . . ?
C37A C36A H36C 107.7 . . ?
O9A C36A H36D 107.7 . . ?
C37A C36A H36D 107.7 . . ?
H36C C36A H36D 107.1 . . ?
O10A C37A C36A 91.4(5) . . ?
O10A C37A H37C 113.4 . . ?
C36A C37A H37C 113.4 . . ?
O10A C37A H37D 113.4 . . ?
C36A C37A H37D 113.4 . . ?
H37C C37A H37D 110.7 . . ?
O10A C38A H38D 109.5 . . ?
O10A C38A H38E 109.5 . . ?
H38D C38A H38E 109.5 . . ?
O10A C38A H38F 109.5 . . ?
H38D C38A H38F 109.5 . . ?
H38E C38A H38F 109.5 . . ?
C33B O8B C34B 128.1(6) . . ?
C35B O9B C36B 112.4(7) . . ?
C37B O10B C38B 111.6(7) . . ?
O7 C32B C33B 111.3(6) . . ?
O7 C32B H32E 109.4 . . ?
C33B C32B H32E 109.4 . . ?
O7 C32B H32F 109.4 . . ?
C33B C32B H32F 109.4 . . ?
H32E C32B H32F 108.0 . . ?
O8B C33B C32B 111.8(6) . . ?
O8B C33B H33E 109.3 . . ?
C32B C33B H33E 109.3 . . ?
O8B C33B H33F 109.3 . . ?
C32B C33B H33F 109.3 . . ?
H33E C33B H33F 107.9 . . ?
O8B C34B C35B 114.5(6) . . ?
O8B C34B H34E 108.6 . . ?
C35B C34B H34E 108.6 . . ?
O8B C34B H34F 108.6 . . ?
C35B C34B H34F 108.6 . . ?
H34E C34B H34F 107.6 . . ?
O9B C35B C34B 121.0(7) . . ?
O9B C35B H35E 107.1 . . ?
C34B C35B H35E 107.1 . . ?
O9B C35B H35F 107.1 . . ?
C34B C35B H35F 107.1 . . ?
H35E C35B H35F 106.8 . . ?
O9B C36B C37B 101.2(6) . . ?
O9B C36B H36E 111.5 . . ?
C37B C36B H36E 111.5 . . ?
O9B C36B H36F 111.5 . . ?
C37B C36B H36F 111.5 . . ?
H36E C36B H36F 109.3 . . ?
O10B C37B C36B 103.3(7) . . ?
O10B C37B H37E 111.1 . . ?
C36B C37B H37E 111.1 . . ?
O10B C37B H37F 111.1 . . ?
C36B C37B H37F 111.1 . . ?
H37E C37B H37F 109.1 . . ?
O10B C38B H38G 109.5 . . ?
O10B C38B H38H 109.5 . . ?
H38G C38B H38H 109.5 . . ?
O10B C38B H38I 109.5 . . ?
H38G C38B H38I 109.5 . . ?
H38H C38B H38I 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O3 0.71(3) 2.33(3) 2.668(4) 111(3) .
N1 H1N N3 0.71(3) 2.06(3) 2.692(3) 148(3) .
N2 H2N N4 0.60(2) 2.21(2) 2.710(2) 143(3) .

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.016



####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1487438'
_audit_update_record             
;
2016-06-23 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;

_chemical_compound_source        'Nathalie Busschaert'
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H11 N O4'
_chemical_formula_sum            'C11 H11 N O4'
_chemical_formula_weight         221.21

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                   3.8385(6)
_cell_length_b                   10.3480(17)
_cell_length_c                   12.844(2)
_cell_angle_alpha                93.967(3)
_cell_angle_beta                 90.145(3)
_cell_angle_gamma                95.188(3)
_cell_volume                     506.86(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3954
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.82

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9353
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.589
_diffrn_reflns_theta_max         27.902
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2393
_reflns_number_gt                2029
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.0998P)²+0.2279P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2393
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1662
_refine_ls_wR_factor_gt          0.1581
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5503(5) 0.78580(19) 0.48551(13) 0.0297(4) Uani 1 1 d . . . . .
H1A H 0.4403 0.6977 0.4682 0.045 Uiso 1 1 calc R U . . .
H1B H 0.4465 0.8470 0.4423 0.045 Uiso 1 1 calc R U . . .
H1C H 0.8020 0.7880 0.4721 0.045 Uiso 1 1 calc R U . . .
C2 C 0.4924(4) 0.82379(17) 0.59891(13) 0.0239(4) Uani 1 1 d . . . . .
C3 C 0.2056(4) 0.73546(15) 0.75650(12) 0.0198(3) Uani 1 1 d . . . . .
C4 C 0.2938(4) 0.84306(15) 0.82669(13) 0.0209(3) Uani 1 1 d . . . . .
H4 H 0.4272 0.9175 0.8038 0.025 Uiso 1 1 calc R U . . .
C5 C 0.1866(4) 0.84097(15) 0.92929(12) 0.0207(3) Uani 1 1 d . . . . .
H5 H 0.2496 0.9143 0.9764 0.025 Uiso 1 1 calc R U . . .
C6 C -0.0124(4) 0.73336(15) 0.96545(12) 0.0193(3) Uani 1 1 d . . . . .
C7 C -0.1033(4) 0.62684(15) 0.89612(13) 0.0201(3) Uani 1 1 d . . . . .
H7 H -0.2392 0.5534 0.9197 0.024 Uiso 1 1 calc R U . . .
C8 C 0.0017(4) 0.62608(15) 0.79239(12) 0.0195(3) Uani 1 1 d . . . . .
C9 C -0.1069(4) 0.50817(16) 0.72552(13) 0.0236(4) Uani 1 1 d . . . . .
H9 H -0.2535 0.4425 0.7561 0.028 Uiso 1 1 calc R U . . .
C10 C -0.1350(4) 0.72897(15) 1.07467(13) 0.0202(3) Uani 1 1 d . . . . .
C11 C -0.1386(4) 0.83821(17) 1.24172(13) 0.0240(4) Uani 1 1 d . . . . .
H11A H -0.0445 0.9195 1.2794 0.036 Uiso 1 1 calc R U . . .
H11B H -0.3948 0.8321 1.2432 0.036 Uiso 1 1 calc R U . . .
H11C H -0.0552 0.7643 1.2751 0.036 Uiso 1 1 calc R U . . .
N1 N 0.3058(4) 0.72977(14) 0.65190(11) 0.0223(3) Uani 1 1 d . . . . .
O1 O 0.6049(3) 0.92951(12) 0.63924(10) 0.0298(3) Uani 1 1 d . . . . .
O2 O -0.0271(3) 0.48655(12) 0.63454(10) 0.0307(3) Uani 1 1 d . . . . .
O3 O -0.3183(3) 0.63947(11) 1.10733(9) 0.0261(3) Uani 1 1 d . . . . .
O4 O -0.0222(3) 0.83632(11) 1.13454(9) 0.0229(3) Uani 1 1 d . . . . .
H1N H 0.240(6) 0.658(2) 0.6143(16) 0.029(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.505(2) . ?
C2 O1 1.219(2) . ?
C2 N1 1.375(2) . ?
C3 N1 1.397(2) . ?
C3 C4 1.399(2) . ?
C3 C8 1.421(2) . ?
C4 C5 1.383(2) . ?
C5 C6 1.400(2) . ?
C6 C7 1.387(2) . ?
C6 C10 1.483(2) . ?
C7 C8 1.393(2) . ?
C8 C9 1.470(2) . ?
C9 O2 1.220(2) . ?
C10 O3 1.211(2) . ?
C10 O4 1.3439(19) . ?
C11 O4 1.4478(19) . ?

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
O1 C2 N1 123.64(16) . . ?
O1 C2 C1 121.90(15) . . ?
N1 C2 C1 114.46(15) . . ?
N1 C3 C4 123.38(14) . . ?
N1 C3 C8 117.76(14) . . ?
C4 C3 C8 118.85(14) . . ?
C5 C4 C3 119.97(14) . . ?
C4 C5 C6 121.56(14) . . ?
C7 C6 C5 118.78(15) . . ?
C7 C6 C10 118.43(14) . . ?
C5 C6 C10 122.79(14) . . ?
C6 C7 C8 120.91(14) . . ?
C7 C8 C3 119.92(14) . . ?
C7 C8 C9 116.59(14) . . ?
C3 C8 C9 123.49(14) . . ?
O2 C9 C8 126.31(15) . . ?
O3 C10 O4 122.99(15) . . ?
O3 C10 C6 124.36(14) . . ?
O4 C10 C6 112.65(13) . . ?
C2 N1 C3 128.40(14) . . ?
C10 O4 C11 115.04(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O2 0.87(2) 2.00(2) 2.7123(19) 137.7(18) .

_refine_diff_density_max         0.520
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.076



