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

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

data_3c
_database_code_depnum_ccdc_archive 'CCDC 1556665'
_audit_update_record             
;
2017-06-17 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 N3 O6'
_chemical_formula_sum            'C21 H23 N3 O6'
_chemical_formula_weight         413.42

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1043(15)
_cell_length_b                   10.3101(17)
_cell_length_c                   12.910(2)
_cell_angle_alpha                108.789(4)
_cell_angle_beta                 106.251(4)
_cell_angle_gamma                98.820(5)
_cell_volume                     1061.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9384
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      27.58

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15493
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_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         1.78
_diffrn_reflns_theta_max         27.58
_reflns_number_total             4797
_reflns_number_gt                3989
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0956P)²+0.2885P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.26(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4797
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1712
_refine_ls_wR_factor_gt          0.1566
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.23366(19) 0.62379(18) 0.39515(14) 0.0419(4) Uani 1 1 d . . .
H1 H 0.3417 0.6375 0.4081 0.050 Uiso 1 1 calc R . .
C2 C 0.1831(2) 0.67726(19) 0.48796(14) 0.0469(4) Uani 1 1 d . . .
H2 H 0.2580 0.7264 0.5627 0.056 Uiso 1 1 calc R . .
C3 C 0.0223(2) 0.65924(17) 0.47198(15) 0.0445(4) Uani 1 1 d . . .
C4 C -0.0327(3) 0.7149(2) 0.57370(19) 0.0629(6) Uani 1 1 d . . .
H4A H 0.0367 0.8067 0.6269 0.094 Uiso 1 1 calc R . .
H4B H -0.0308 0.6505 0.6134 0.094 Uiso 1 1 calc R . .
H4C H -0.1389 0.7229 0.5456 0.094 Uiso 1 1 calc R . .
C5 C -0.0860(2) 0.58582(19) 0.35976(16) 0.0477(4) Uani 1 1 d . . .
H5 H -0.1940 0.5721 0.3469 0.057 Uiso 1 1 calc R . .
C6 C -0.03687(18) 0.53240(17) 0.26612(14) 0.0388(4) Uani 1 1 d . . .
H6 H -0.1120 0.4844 0.1913 0.047 Uiso 1 1 calc R . .
C7 C 0.12384(16) 0.54970(14) 0.28274(12) 0.0308(3) Uani 1 1 d . . .
C8 C 0.16882(16) 0.48777(14) 0.17724(12) 0.0289(3) Uani 1 1 d . . .
H8 H 0.0736 0.4634 0.1086 0.035 Uiso 1 1 calc R . .
C9 C 0.22686(17) 0.34959(14) 0.16278(13) 0.0323(3) Uani 1 1 d . . .
C10 C 0.3504(2) 0.36631(18) 0.27187(15) 0.0442(4) Uani 1 1 d . . .
C11 C 0.09589(19) 0.22599(15) 0.13508(14) 0.0388(4) Uani 1 1 d . . .
C12 C 0.30043(16) 0.33828(14) 0.06197(13) 0.0326(3) Uani 1 1 d . . .
C13 C 0.46716(18) 0.31615(17) 0.10063(14) 0.0409(4) Uani 1 1 d . . .
C14 C 0.6159(3) 0.1566(3) 0.1299(3) 0.0825(8) Uani 1 1 d . . .
H14A H 0.6708 0.1663 0.0781 0.124 Uiso 1 1 calc R . .
H14B H 0.6020 0.0619 0.1289 0.124 Uiso 1 1 calc R . .
H14C H 0.6769 0.2239 0.2078 0.124 Uiso 1 1 calc R . .
C15 C 0.19224(17) 0.21975(15) -0.05418(13) 0.0350(3) Uani 1 1 d . . .
H15A H 0.1747 0.1302 -0.0440 0.042 Uiso 1 1 calc R . .
H15B H 0.0902 0.2396 -0.0787 0.042 Uiso 1 1 calc R . .
C16 C 0.26483(19) 0.20751(16) -0.14696(14) 0.0385(4) Uani 1 1 d . . .
O4 O 0.16136(17) 0.12332(17) -0.25164(11) 0.0629(4) Uani 1 1 d . . .
C17 C 0.2205(3) 0.0998(3) -0.34704(19) 0.0771(7) Uani 1 1 d . . .
H17A H 0.2621 0.1894 -0.3498 0.116 Uiso 1 1 calc R . .
H17B H 0.1355 0.0417 -0.4193 0.116 Uiso 1 1 calc R . .
H17C H 0.3031 0.0525 -0.3354 0.116 Uiso 1 1 calc R . .
C18 C 0.30343(16) 0.57768(14) 0.15989(13) 0.0326(3) Uani 1 1 d . . .
H18 H 0.4038 0.6042 0.2249 0.039 Uiso 1 1 calc R . .
C19 C 0.26010(18) 0.70759(15) 0.14427(14) 0.0366(3) Uani 1 1 d . . .
C20 C 0.2871(3) 0.9508(2) 0.2505(2) 0.0737(7) Uani 1 1 d . . .
H20A H 0.3440 0.9981 0.2137 0.088 Uiso 1 1 calc R . .
H20B H 0.1741 0.9316 0.2100 0.088 Uiso 1 1 calc R . .
C21 C 0.3298(7) 1.0397(4) 0.3723(4) 0.1388(17) Uani 1 1 d . . .
H21A H 0.2781 0.9894 0.4090 0.208 Uiso 1 1 calc R . .
H21B H 0.2969 1.1252 0.3787 0.208 Uiso 1 1 calc R . .
H21C H 0.4428 1.0635 0.4103 0.208 Uiso 1 1 calc R . .
N1 N 0.4475(3) 0.3769(2) 0.35406(17) 0.0762(6) Uani 1 1 d . . .
N2 N -0.0053(2) 0.13427(16) 0.11873(16) 0.0584(5) Uani 1 1 d . . .
N3 N 0.30830(19) 0.47681(14) 0.05305(13) 0.0422(4) Uani 1 1 d . . .
O1 O 0.58660(14) 0.40989(16) 0.13706(14) 0.0648(4) Uani 1 1 d . . .
O2 O 0.46095(15) 0.18340(14) 0.09170(12) 0.0526(3) Uani 1 1 d . . .
O3 O 0.39987(16) 0.26225(16) -0.12971(12) 0.0652(4) Uani 1 1 d . . .
O5 O 0.17196(18) 0.70979(15) 0.05757(13) 0.0630(4) Uani 1 1 d . . .
O6 O 0.32878(16) 0.81908(12) 0.24463(11) 0.0516(4) Uani 1 1 d . . .
H3A H 0.387(3) 0.501(2) 0.040(2) 0.064(7) 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 1.383(2) . ?
C1 C7 1.389(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.394(3) . ?
C2 H2 0.9300 . ?
C3 C5 1.382(3) . ?
C3 C4 1.508(2) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.392(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.5043(18) . ?
C8 C18 1.5332(19) . ?
C8 C9 1.5679(19) . ?
C8 H8 0.9800 . ?
C9 C11 1.475(2) . ?
C9 C10 1.475(2) . ?
C9 C12 1.6031(19) . ?
C10 N1 1.136(2) . ?
C11 N2 1.133(2) . ?
C12 N3 1.4621(19) . ?
C12 C15 1.528(2) . ?
C12 C13 1.537(2) . ?
C13 O1 1.198(2) . ?
C13 O2 1.327(2) . ?
C14 O2 1.459(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.503(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O3 1.197(2) . ?
C16 O4 1.322(2) . ?
O4 C17 1.443(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 N3 1.4528(19) . ?
C18 C19 1.511(2) . ?
C18 H18 0.9800 . ?
C19 O5 1.190(2) . ?
C19 O6 1.3259(19) . ?
C20 C21 1.445(5) . ?
C20 O6 1.450(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N3 H3A 0.81(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
C2 C1 C7 120.26(15) . . ?
C2 C1 H1 119.9 . . ?
C7 C1 H1 119.9 . . ?
C1 C2 C3 121.52(15) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C5 C3 C2 117.79(14) . . ?
C5 C3 C4 120.80(17) . . ?
C2 C3 C4 121.40(17) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 C6 121.23(15) . . ?
C3 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C7 120.72(15) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C1 C7 C6 118.46(13) . . ?
C1 C7 C8 123.62(13) . . ?
C6 C7 C8 117.92(12) . . ?
C7 C8 C18 119.35(11) . . ?
C7 C8 C9 117.28(11) . . ?
C18 C8 C9 99.30(10) . . ?
C7 C8 H8 106.6 . . ?
C18 C8 H8 106.6 . . ?
C9 C8 H8 106.6 . . ?
C11 C9 C10 106.90(13) . . ?
C11 C9 C8 111.43(12) . . ?
C10 C9 C8 110.88(12) . . ?
C11 C9 C12 114.75(11) . . ?
C10 C9 C12 110.46(12) . . ?
C8 C9 C12 102.46(10) . . ?
N1 C10 C9 178.10(19) . . ?
N2 C11 C9 176.77(17) . . ?
N3 C12 C15 110.19(13) . . ?
N3 C12 C13 110.96(12) . . ?
C15 C12 C13 111.33(11) . . ?
N3 C12 C9 103.02(10) . . ?
C15 C12 C9 111.45(11) . . ?
C13 C12 C9 109.61(12) . . ?
O1 C13 O2 125.18(16) . . ?
O1 C13 C12 123.10(16) . . ?
O2 C13 C12 111.70(13) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C12 110.89(12) . . ?
C16 C15 H15A 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 108.0 . . ?
O3 C16 O4 123.44(15) . . ?
O3 C16 C15 125.28(14) . . ?
O4 C16 C15 111.24(13) . . ?
C16 O4 C17 115.91(16) . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 C19 112.12(13) . . ?
N3 C18 C8 100.37(11) . . ?
C19 C18 C8 110.45(11) . . ?
N3 C18 H18 111.2 . . ?
C19 C18 H18 111.2 . . ?
C8 C18 H18 111.2 . . ?
O5 C19 O6 124.55(15) . . ?
O5 C19 C18 125.91(14) . . ?
O6 C19 C18 109.44(13) . . ?
C21 C20 O6 107.7(2) . . ?
C21 C20 H20A 110.2 . . ?
O6 C20 H20A 110.2 . . ?
C21 C20 H20B 110.2 . . ?
O6 C20 H20B 110.2 . . ?
H20A C20 H20B 108.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 N3 C12 109.14(12) . . ?
C18 N3 H3A 112.8(17) . . ?
C12 N3 H3A 108.9(16) . . ?
C13 O2 C14 114.28(17) . . ?
C19 O6 C20 117.50(15) . . ?

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
N3 H3A O3 0.81(3) 2.55(2) 3.146(2) 131(2) 2_665

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.099
####################################################################### 
# 
# 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_4m
_database_code_depnum_ccdc_archive 'CCDC 1556671'
_audit_update_record             
;
2017-06-17 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H25 N3 O8'
_chemical_formula_sum            'C21 H25 N3 O8'
_chemical_formula_weight         447.44

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3301(13)
_cell_length_b                   10.6104(13)
_cell_length_c                   12.2479(15)
_cell_angle_alpha                68.368(3)
_cell_angle_beta                 82.297(3)
_cell_angle_gamma                61.873(3)
_cell_volume                     1099.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.52

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16485
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_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         1.79
_diffrn_reflns_theta_max         27.58
_reflns_number_total             5010
_reflns_number_gt                4198
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0747P)²+0.3101P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5010
_refine_ls_number_parameters     305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1374
_refine_ls_wR_factor_gt          0.1189
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.45032(16) 0.65465(17) 0.68205(13) 0.0301(3) Uani 1 1 d . . .
H1 H 0.4593 0.5825 0.7564 0.036 Uiso 1 1 calc R . .
C2 C 0.57492(16) 0.66072(18) 0.62893(13) 0.0317(3) Uani 1 1 d . . .
H2A H 0.6667 0.5930 0.6674 0.038 Uiso 1 1 calc R . .
C3 C 0.56329(15) 0.76789(17) 0.51800(13) 0.0273(3) Uani 1 1 d . . .
C4 C 0.68563(19) 0.8803(2) 0.36344(15) 0.0387(4) Uani 1 1 d . . .
H4A H 0.6461 0.8702 0.3023 0.058 Uiso 1 1 calc R . .
H4B H 0.7823 0.8709 0.3447 0.058 Uiso 1 1 calc R . .
H4C H 0.6231 0.9784 0.3701 0.058 Uiso 1 1 calc R . .
C5 C 0.42623(16) 0.86865(17) 0.46105(13) 0.0323(3) Uani 1 1 d . . .
H5 H 0.4175 0.9408 0.3868 0.039 Uiso 1 1 calc R . .
C6 C 0.30201(15) 0.86097(17) 0.51595(13) 0.0292(3) Uani 1 1 d . . .
H6 H 0.2103 0.9291 0.4775 0.035 Uiso 1 1 calc R . .
C7 C 0.31101(14) 0.75471(15) 0.62636(12) 0.0237(3) Uani 1 1 d . . .
C8 C 0.17176(14) 0.74908(15) 0.67929(11) 0.0219(3) Uani 1 1 d . . .
H8 H 0.0893 0.8492 0.6409 0.026 Uiso 1 1 calc R . .
C9 C 0.14037(14) 0.62794(15) 0.66237(11) 0.0215(3) Uani 1 1 d . . .
C10 C 0.27455(15) 0.48029(16) 0.69276(12) 0.0272(3) Uani 1 1 d . . .
C11 C 0.07979(14) 0.68174(16) 0.53543(11) 0.0245(3) Uani 1 1 d . . .
C12 C 0.02613(14) 0.61199(15) 0.76084(11) 0.0220(3) Uani 1 1 d . . .
C13 C 0.03956(15) 0.45186(16) 0.79581(12) 0.0259(3) Uani 1 1 d . . .
C14 C 0.1351(2) 0.20374(19) 0.93560(16) 0.0476(5) Uani 1 1 d . . .
H14A H 0.0416 0.2035 0.9421 0.071 Uiso 1 1 calc R . .
H14B H 0.1878 0.1465 1.0107 0.071 Uiso 1 1 calc R . .
H14C H 0.1907 0.1581 0.8791 0.071 Uiso 1 1 calc R . .
C15 C -0.13430(15) 0.72992(17) 0.71956(12) 0.0284(3) Uani 1 1 d . . .
H15A H -0.1447 0.8323 0.6959 0.034 Uiso 1 1 calc R . .
H15B H -0.1619 0.7185 0.6524 0.034 Uiso 1 1 calc R . .
C16 C -0.23299(16) 0.70531(19) 0.81921(13) 0.0327(3) Uani 1 1 d . . .
C17 C -0.4556(3) 0.8210(4) 0.9058(2) 0.0853(9) Uani 1 1 d . . .
H17A H -0.5106 0.7808 0.8846 0.128 Uiso 1 1 calc R . .
H17B H -0.5214 0.9195 0.9104 0.128 Uiso 1 1 calc R . .
H17C H -0.4048 0.7533 0.9807 0.128 Uiso 1 1 calc R . .
C18 C 0.16249(15) 0.71542(16) 0.81344(11) 0.0244(3) Uani 1 1 d . . .
H18 H 0.2609 0.6460 0.8513 0.029 Uiso 1 1 calc R . .
C19 C 0.10310(17) 0.86342(17) 0.83671(12) 0.0293(3) Uani 1 1 d . . .
C20 C -0.1024(2) 1.10244(19) 0.81570(17) 0.0444(4) Uani 1 1 d . . .
H20A H -0.0521 1.1612 0.7700 0.053 Uiso 1 1 calc R . .
H20B H -0.0938 1.0880 0.8978 0.053 Uiso 1 1 calc R . .
C21 C -0.2588(3) 1.1842(3) 0.7757(3) 0.0744(7) Uani 1 1 d . . .
H21A H -0.2664 1.1970 0.6947 0.112 Uiso 1 1 calc R . .
H21B H -0.3036 1.2825 0.7840 0.112 Uiso 1 1 calc R . .
H21C H -0.3081 1.1264 0.8225 0.112 Uiso 1 1 calc R . .
N1 N 0.37503(16) 0.36363(17) 0.72061(15) 0.0458(4) Uani 1 1 d . . .
N2 N 0.11481(17) 0.57378(18) 0.49055(12) 0.0358(3) Uani 1 1 d . . .
N3 N 0.06849(13) 0.64013(14) 0.85515(10) 0.0241(2) Uani 1 1 d . . .
O1 O 0.69351(11) 0.76353(13) 0.47229(10) 0.0363(3) Uani 1 1 d . . .
O2 O 0.00246(12) 0.81703(12) 0.48371(9) 0.0363(3) Uani 1 1 d . . .
O3 O -0.00508(14) 0.41522(14) 0.73267(9) 0.0395(3) Uani 1 1 d . . .
O4 O 0.11291(12) 0.35860(11) 0.89784(9) 0.0314(2) Uani 1 1 d . . .
O5 O -0.21124(13) 0.58337(15) 0.89151(10) 0.0443(3) Uani 1 1 d . . .
O6 O -0.34947(14) 0.83517(16) 0.81713(12) 0.0564(4) Uani 1 1 d . . .
O7 O 0.17576(15) 0.89462(17) 0.88063(14) 0.0575(4) Uani 1 1 d . . .
O8 O -0.03692(12) 0.95559(12) 0.80037(10) 0.0360(3) Uani 1 1 d . . .
H3 H 0.110(2) 0.556(2) 0.9163(16) 0.034(4) Uiso 1 1 d . . .
H2B H 0.076(2) 0.603(3) 0.421(2) 0.052(6) Uiso 1 1 d . . .
H2C H 0.174(2) 0.476(2) 0.5296(18) 0.042(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 1.381(2) . ?
C1 C7 1.3972(19) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(2) . ?
C2 H2A 0.9300 . ?
C3 O1 1.3725(17) . ?
C3 C5 1.386(2) . ?
C4 O1 1.4266(19) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.390(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.3853(19) . ?
C6 H6 0.9300 . ?
C7 C8 1.5151(18) . ?
C8 C18 1.5472(18) . ?
C8 C9 1.5516(18) . ?
C8 H8 0.9800 . ?
C9 C10 1.4748(19) . ?
C9 C11 1.5507(17) . ?
C9 C12 1.5913(18) . ?
C10 N1 1.139(2) . ?
C11 O2 1.2182(18) . ?
C11 N2 1.329(2) . ?
C12 N3 1.4587(17) . ?
C12 C13 1.5319(19) . ?
C12 C15 1.5397(19) . ?
C13 O3 1.2034(17) . ?
C13 O4 1.3229(17) . ?
C14 O4 1.4420(18) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.510(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O5 1.201(2) . ?
C16 O6 1.329(2) . ?
C17 O6 1.456(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 N3 1.4627(17) . ?
C18 C19 1.516(2) . ?
C18 H18 0.9800 . ?
C19 O7 1.1983(18) . ?
C19 O8 1.3284(19) . ?
C20 O8 1.4521(19) . ?
C20 C21 1.476(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N2 H2B 0.88(2) . ?
N2 H2C 0.89(2) . ?
N3 H3 0.878(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 C7 121.31(13) . . ?
C2 C1 H1 119.3 . . ?
C7 C1 H1 119.3 . . ?
C1 C2 C3 120.03(13) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
O1 C3 C5 124.69(13) . . ?
O1 C3 C2 115.57(13) . . ?
C5 C3 C2 119.74(13) . . ?
O1 C4 H4A 109.5 . . ?
O1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 C6 119.42(13) . . ?
C3 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C7 C6 C5 121.84(13) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C1 117.65(12) . . ?
C6 C7 C8 119.09(12) . . ?
C1 C7 C8 123.24(12) . . ?
C7 C8 C18 115.86(11) . . ?
C7 C8 C9 115.14(11) . . ?
C18 C8 C9 103.43(10) . . ?
C7 C8 H8 107.3 . . ?
C18 C8 H8 107.3 . . ?
C9 C8 H8 107.3 . . ?
C10 C9 C11 111.79(11) . . ?
C10 C9 C8 109.81(11) . . ?
C11 C9 C8 110.98(11) . . ?
C10 C9 C12 107.75(11) . . ?
C11 C9 C12 114.04(10) . . ?
C8 C9 C12 101.99(10) . . ?
N1 C10 C9 176.82(16) . . ?
O2 C11 N2 123.96(13) . . ?
O2 C11 C9 119.47(12) . . ?
N2 C11 C9 116.56(13) . . ?
N3 C12 C13 114.10(11) . . ?
N3 C12 C15 108.69(11) . . ?
C13 C12 C15 108.63(11) . . ?
N3 C12 C9 104.31(10) . . ?
C13 C12 C9 107.85(10) . . ?
C15 C12 C9 113.33(10) . . ?
O3 C13 O4 124.76(13) . . ?
O3 C13 C12 122.53(12) . . ?
O4 C13 C12 112.57(11) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C12 109.03(11) . . ?
C16 C15 H15A 109.9 . . ?
C12 C15 H15A 109.9 . . ?
C16 C15 H15B 109.9 . . ?
C12 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
O5 C16 O6 123.34(14) . . ?
O5 C16 C15 124.68(15) . . ?
O6 C16 C15 111.97(13) . . ?
O6 C17 H17A 109.5 . . ?
O6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 C19 113.06(11) . . ?
N3 C18 C8 106.57(10) . . ?
C19 C18 C8 109.25(11) . . ?
N3 C18 H18 109.3 . . ?
C19 C18 H18 109.3 . . ?
C8 C18 H18 109.3 . . ?
O7 C19 O8 124.02(15) . . ?
O7 C19 C18 123.52(15) . . ?
O8 C19 C18 112.44(12) . . ?
O8 C20 C21 108.29(16) . . ?
O8 C20 H20A 110.0 . . ?
C21 C20 H20A 110.0 . . ?
O8 C20 H20B 110.0 . . ?
C21 C20 H20B 110.0 . . ?
H20A C20 H20B 108.4 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 N2 H2B 116.6(15) . . ?
C11 N2 H2C 121.9(13) . . ?
H2B N2 H2C 122(2) . . ?
C12 N3 C18 111.42(10) . . ?
C12 N3 H3 112.1(12) . . ?
C18 N3 H3 111.1(12) . . ?
C3 O1 C4 117.36(12) . . ?
C13 O4 C14 116.23(12) . . ?
C16 O6 C17 115.70(17) . . ?
C19 O8 C20 116.49(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
N3 H3 O4 0.878(19) 2.180(18) 2.6509(15) 113.1(14) .
N3 H3 O5 0.878(19) 2.335(19) 3.1513(17) 154.7(16) 2_567
N2 H2B O3 0.88(2) 2.21(2) 3.0404(17) 158(2) 2_566
N2 H2C O1 0.89(2) 2.25(2) 3.049(2) 148.2(17) 2_666

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.080

#===================================================
####################################################################### 
# 
# 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_3d
_database_code_depnum_ccdc_archive 'CCDC 1556666'
_audit_update_record             
;
2017-06-17 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 N3 O7'
_chemical_formula_sum            'C21 H23 N3 O7'
_chemical_formula_weight         429.42

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2898(13)
_cell_length_b                   10.3345(13)
_cell_length_c                   10.6805(16)
_cell_angle_alpha                110.213(4)
_cell_angle_beta                 92.129(4)
_cell_angle_gamma                94.620(4)
_cell_volume                     1059.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6088
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      27.22

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16275
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         27.59
_reflns_number_total             4888
_reflns_number_gt                3265
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0764P)²+0.4936P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4888
_refine_ls_number_parameters     288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1752
_refine_ls_wR_factor_gt          0.1462
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6958(2) 0.2755(2) 0.5381(2) 0.0371(5) Uani 1 1 d . . .
H1 H 0.6352 0.3260 0.5921 0.044 Uiso 1 1 calc R . .
C2 C 0.8093(2) 0.2512(3) 0.5957(3) 0.0450(6) Uani 1 1 d . . .
C3 C 0.7461(3) 0.3635(4) 0.8176(3) 0.0718(9) Uani 1 1 d . . .
H3A H 0.7267 0.4457 0.8011 0.108 Uiso 1 1 calc R . .
H3B H 0.7796 0.3879 0.9088 0.108 Uiso 1 1 calc R . .
H3C H 0.6680 0.3012 0.8018 0.108 Uiso 1 1 calc R . .
C4 C 0.8993(2) 0.1763(3) 0.5161(3) 0.0547(7) Uani 1 1 d . . .
H4 H 0.9758 0.1594 0.5544 0.066 Uiso 1 1 calc R . .
C5 C 0.8749(2) 0.1269(3) 0.3797(3) 0.0547(7) Uani 1 1 d . . .
H5 H 0.9361 0.0771 0.3261 0.066 Uiso 1 1 calc R . .
C6 C 0.7612(2) 0.1494(2) 0.3199(3) 0.0447(6) Uani 1 1 d . . .
H6 H 0.7458 0.1143 0.2273 0.054 Uiso 1 1 calc R . .
C7 C 0.6714(2) 0.2246(2) 0.3995(2) 0.0331(5) Uani 1 1 d . . .
C8 C 0.5432(2) 0.2524(2) 0.3451(2) 0.0307(4) Uani 1 1 d . . .
H8 H 0.5120 0.3300 0.4160 0.037 Uiso 1 1 calc R . .
C9 C 0.4317(2) 0.1308(2) 0.3068(2) 0.0317(5) Uani 1 1 d . . .
C10 C 0.3879(2) 0.1049(2) 0.4260(2) 0.0370(5) Uani 1 1 d . . .
C11 C 0.4733(2) 0.0012(2) 0.2125(2) 0.0371(5) Uani 1 1 d . . .
C12 C 0.5420(2) 0.2912(2) 0.2191(2) 0.0333(5) Uani 1 1 d . . .
H12 H 0.6001 0.2368 0.1551 0.040 Uiso 1 1 calc R . .
C13 C 0.5801(2) 0.4455(2) 0.2539(2) 0.0364(5) Uani 1 1 d . . .
C14 C 0.6307(3) 0.6192(3) 0.1572(4) 0.0776(10) Uani 1 1 d . . .
H14A H 0.5883 0.6262 0.0775 0.093 Uiso 1 1 calc R . .
H14B H 0.5864 0.6736 0.2335 0.093 Uiso 1 1 calc R . .
C15 C 0.7629(4) 0.6751(4) 0.1705(5) 0.1060(15) Uani 1 1 d . . .
H15A H 0.8033 0.6764 0.2534 0.159 Uiso 1 1 calc R . .
H15B H 0.7666 0.7679 0.1695 0.159 Uiso 1 1 calc R . .
H15C H 0.8084 0.6189 0.0975 0.159 Uiso 1 1 calc R . .
C16 C 0.3266(2) 0.1866(2) 0.2312(2) 0.0331(5) Uani 1 1 d . . .
C17 C 0.2404(2) 0.0654(2) 0.1289(2) 0.0378(5) Uani 1 1 d . . .
C18 C 0.0702(3) -0.1103(3) 0.1030(3) 0.0593(7) Uani 1 1 d . . .
H18A H 0.0001 -0.0760 0.0659 0.089 Uiso 1 1 calc R . .
H18B H 0.0351 -0.1639 0.1539 0.089 Uiso 1 1 calc R . .
H18C H 0.1170 -0.1677 0.0320 0.089 Uiso 1 1 calc R . .
C19 C 0.2441(2) 0.2832(2) 0.3323(2) 0.0413(5) Uani 1 1 d . . .
H19A H 0.2106 0.2369 0.3912 0.050 Uiso 1 1 calc R . .
H19B H 0.2993 0.3656 0.3866 0.050 Uiso 1 1 calc R . .
C20 C 0.1316(2) 0.3252(2) 0.2664(3) 0.0445(6) Uani 1 1 d . . .
C21 C -0.0480(3) 0.4574(3) 0.3080(4) 0.0742(9) Uani 1 1 d . . .
H21A H -0.0251 0.5039 0.2469 0.111 Uiso 1 1 calc R . .
H21B H -0.0885 0.5190 0.3819 0.111 Uiso 1 1 calc R . .
H21C H -0.1079 0.3770 0.2627 0.111 Uiso 1 1 calc R . .
N1 N 0.3567(2) 0.0899(2) 0.5208(2) 0.0601(6) Uani 1 1 d . . .
N2 N 0.4998(2) -0.0984(2) 0.1351(2) 0.0553(6) Uani 1 1 d . . .
N3 N 0.40569(19) 0.2605(2) 0.1622(2) 0.0402(5) Uani 1 1 d . . .
O1 O 0.84135(19) 0.2978(2) 0.73047(19) 0.0654(6) Uani 1 1 d . . .
O2 O 0.5709(2) 0.53124(18) 0.36073(19) 0.0674(6) Uani 1 1 d . . .
O3 O 0.6172(2) 0.47328(18) 0.14818(19) 0.0628(6) Uani 1 1 d . . .
O4 O 0.24974(18) 0.0281(2) 0.01097(17) 0.0591(5) Uani 1 1 d . . .
O5 O 0.15854(15) 0.00559(17) 0.18977(15) 0.0446(4) Uani 1 1 d . . .
O6 O 0.1009(2) 0.2824(2) 0.1492(2) 0.0725(6) Uani 1 1 d . . .
O7 O 0.06877(18) 0.41551(19) 0.35698(19) 0.0598(5) Uani 1 1 d . . .
H3D H 0.399(3) 0.216(3) 0.083(3) 0.049(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 1.381(3) . ?
C1 C7 1.395(3) . ?
C1 H1 0.9300 . ?
C2 O1 1.368(3) . ?
C2 C4 1.378(4) . ?
C3 O1 1.423(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.509(3) . ?
C8 C12 1.531(3) . ?
C8 C9 1.563(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.468(3) . ?
C9 C11 1.477(3) . ?
C9 C16 1.585(3) . ?
C10 N1 1.130(3) . ?
C11 N2 1.136(3) . ?
C12 N3 1.473(3) . ?
C12 C13 1.521(3) . ?
C12 H12 0.9800 . ?
C13 O2 1.191(3) . ?
C13 O3 1.319(3) . ?
C14 C15 1.417(5) . ?
C14 O3 1.472(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N3 1.457(3) . ?
C16 C19 1.530(3) . ?
C16 C17 1.534(3) . ?
C17 O4 1.193(3) . ?
C17 O5 1.322(3) . ?
C18 O5 1.454(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.501(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 O6 1.195(3) . ?
C20 O7 1.321(3) . ?
C21 O7 1.449(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N3 H3D 0.81(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
C2 C1 C7 120.4(2) . . ?
C2 C1 H1 119.8 . . ?
C7 C1 H1 119.8 . . ?
O1 C2 C4 115.8(2) . . ?
O1 C2 C1 124.3(2) . . ?
C4 C2 C1 120.0(2) . . ?
O1 C3 H3A 109.5 . . ?
O1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C2 119.3(2) . . ?
C5 C4 H4 120.4 . . ?
C2 C4 H4 120.4 . . ?
C4 C5 C6 121.7(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 119.0(2) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C1 119.6(2) . . ?
C6 C7 C8 123.4(2) . . ?
C1 C7 C8 116.95(19) . . ?
C7 C8 C12 118.54(17) . . ?
C7 C8 C9 115.82(16) . . ?
C12 C8 C9 101.77(15) . . ?
C7 C8 H8 106.6 . . ?
C12 C8 H8 106.6 . . ?
C9 C8 H8 106.6 . . ?
C10 C9 C11 108.78(17) . . ?
C10 C9 C8 111.07(17) . . ?
C11 C9 C8 111.89(17) . . ?
C10 C9 C16 115.10(17) . . ?
C11 C9 C16 108.94(17) . . ?
C8 C9 C16 100.95(15) . . ?
N1 C10 C9 177.2(2) . . ?
N2 C11 C9 176.2(3) . . ?
N3 C12 C13 107.90(17) . . ?
N3 C12 C8 105.94(16) . . ?
C13 C12 C8 110.99(17) . . ?
N3 C12 H12 110.6 . . ?
C13 C12 H12 110.6 . . ?
C8 C12 H12 110.6 . . ?
O2 C13 O3 124.2(2) . . ?
O2 C13 C12 124.5(2) . . ?
O3 C13 C12 111.23(19) . . ?
C15 C14 O3 112.6(3) . . ?
C15 C14 H14A 109.1 . . ?
O3 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
O3 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C19 111.70(18) . . ?
N3 C16 C17 109.84(18) . . ?
C19 C16 C17 111.14(17) . . ?
N3 C16 C9 103.47(16) . . ?
C19 C16 C9 110.02(17) . . ?
C17 C16 C9 110.42(17) . . ?
O4 C17 O5 125.1(2) . . ?
O4 C17 C16 124.2(2) . . ?
O5 C17 C16 110.69(18) . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C16 112.60(19) . . ?
C20 C19 H19A 109.1 . . ?
C16 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C16 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
O6 C20 O7 124.1(2) . . ?
O6 C20 C19 125.5(2) . . ?
O7 C20 C19 110.3(2) . . ?
O7 C21 H21A 109.5 . . ?
O7 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O7 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 N3 C12 111.03(17) . . ?
C16 N3 H3D 108.8(19) . . ?
C12 N3 H3D 113.1(19) . . ?
C2 O1 C3 117.9(2) . . ?
C13 O3 C14 118.0(2) . . ?
C17 O5 C18 115.95(19) . . ?
C20 O7 C21 116.1(2) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.105
####################################################################### 
# 
# 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_3i
_database_code_depnum_ccdc_archive 'CCDC 1556668'
_audit_update_record             
;
2017-06-17 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 Cl N3 O6, C H2 Cl2'
_chemical_formula_sum            'C21 H22 Cl3 N3 O6'
_chemical_formula_weight         518.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   11.7002(19)
_cell_length_b                   10.3645(14)
_cell_length_c                   20.605(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.755(5)
_cell_angle_gamma                90.00
_cell_volume                     2475.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9935
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23342
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         27.54
_reflns_number_total             5587
_reflns_number_gt                3969
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1349P)²+2.2158P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.056(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5587
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0865
_refine_ls_wR_factor_ref         0.2564
_refine_ls_wR_factor_gt          0.2264
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9431(3) 0.7971(3) 0.12189(16) 0.0454(8) Uani 1 1 d . . .
H1 H 0.9975 0.8629 0.1257 0.054 Uiso 1 1 calc R . .
C2 C 0.9682(3) 0.6831(3) 0.15503(17) 0.0510(8) Uani 1 1 d . . .
H2 H 1.0388 0.6720 0.1811 0.061 Uiso 1 1 calc R . .
C3 C 0.8877(3) 0.5859(3) 0.14906(16) 0.0480(8) Uani 1 1 d . . .
C4 C 0.7829(3) 0.6014(3) 0.11064(19) 0.0528(9) Uani 1 1 d . . .
H4 H 0.7292 0.5348 0.1069 0.063 Uiso 1 1 calc R . .
C5 C 0.7579(3) 0.7153(3) 0.07782(18) 0.0485(8) Uani 1 1 d . . .
H5 H 0.6869 0.7256 0.0520 0.058 Uiso 1 1 calc R . .
C6 C 0.8378(2) 0.8157(3) 0.08279(14) 0.0364(7) Uani 1 1 d . . .
C7 C 0.8144(2) 0.9442(3) 0.04914(13) 0.0318(6) Uani 1 1 d . . .
H7 H 0.8893 0.9821 0.0438 0.038 Uiso 1 1 calc R . .
C8 C 0.7494(2) 1.0442(3) 0.08715(13) 0.0334(6) Uani 1 1 d . . .
C9 C 0.6434(3) 0.9870(3) 0.10705(15) 0.0411(7) Uani 1 1 d . . .
C10 C 0.8233(3) 1.0894(3) 0.14647(14) 0.0380(7) Uani 1 1 d . . .
C11 C 0.7409(2) 0.9452(3) -0.01852(13) 0.0338(6) Uani 1 1 d . . .
H11 H 0.6766 0.8842 -0.0195 0.041 Uiso 1 1 calc R . .
C12 C 0.8148(2) 0.9125(3) -0.07152(14) 0.0364(7) Uani 1 1 d . . .
C13 C 0.8173(4) 0.8173(5) -0.17529(19) 0.0636(11) Uani 1 1 d . . .
H13A H 0.8872 0.7698 -0.1601 0.076 Uiso 1 1 calc R . .
H13B H 0.8385 0.8961 -0.1961 0.076 Uiso 1 1 calc R . .
C14 C 0.7417(5) 0.7393(6) -0.2223(2) 0.0985(19) Uani 1 1 d . . .
H14A H 0.7151 0.6656 -0.2003 0.148 Uiso 1 1 calc R . .
H14B H 0.7837 0.7109 -0.2566 0.148 Uiso 1 1 calc R . .
H14C H 0.6767 0.7901 -0.2407 0.148 Uiso 1 1 calc R . .
C15 C 0.7166(2) 1.1508(3) 0.03306(13) 0.0335(6) Uani 1 1 d . . .
C16 C 0.6043(2) 1.2186(3) 0.04473(16) 0.0397(7) Uani 1 1 d . . .
C17 C 0.5208(4) 1.3599(5) 0.1137(3) 0.0841(15) Uani 1 1 d . . .
H17A H 0.4937 1.4217 0.0804 0.126 Uiso 1 1 calc R . .
H17B H 0.5398 1.4033 0.1549 0.126 Uiso 1 1 calc R . .
H17C H 0.4616 1.2972 0.1172 0.126 Uiso 1 1 calc R . .
C18 C 0.8160(2) 1.2475(3) 0.03288(16) 0.0403(7) Uani 1 1 d . . .
H18A H 0.8368 1.2814 0.0768 0.048 Uiso 1 1 calc R . .
H18B H 0.8828 1.2032 0.0205 0.048 Uiso 1 1 calc R . .
C19 C 0.7845(3) 1.3572(3) -0.01345(16) 0.0432(7) Uani 1 1 d . . .
C20 C 0.8586(5) 1.5335(5) -0.0655(3) 0.0881(16) Uani 1 1 d . . .
H20A H 0.8171 1.5098 -0.1072 0.132 Uiso 1 1 calc R . .
H20B H 0.9315 1.5705 -0.0718 0.132 Uiso 1 1 calc R . .
H20C H 0.8145 1.5956 -0.0448 0.132 Uiso 1 1 calc R . .
C21 C 0.6078(6) 0.2428(7) 0.3163(3) 0.1034(19) Uani 1 1 d . . .
H21A H 0.5379 0.2940 0.3136 0.124 Uiso 1 1 calc R . .
H21B H 0.6287 0.2170 0.3615 0.124 Uiso 1 1 calc R . .
Cl1 Cl 0.91907(11) 0.44107(9) 0.19005(5) 0.0695(4) Uani 1 1 d . . .
Cl2 Cl 0.5810(2) 0.1070(2) 0.26845(12) 0.1467(9) Uani 1 1 d . . .
Cl3 Cl 0.7149(2) 0.3346(3) 0.29294(14) 0.1776(12) Uani 1 1 d . . .
N1 N 0.5611(3) 0.9454(4) 0.12119(17) 0.0649(9) Uani 1 1 d . . .
N2 N 0.8815(3) 1.1216(3) 0.19197(15) 0.0586(8) Uani 1 1 d . . .
N3 N 0.6974(2) 1.0777(3) -0.02774(12) 0.0413(6) Uani 1 1 d . . .
H3 H 0.6647 1.1083 -0.0644 0.050 Uiso 1 1 calc R . .
O1 O 0.9141(2) 0.9409(3) -0.06966(13) 0.0689(9) Uani 1 1 d . . .
O2 O 0.75627(19) 0.8482(2) -0.12007(11) 0.0494(6) Uani 1 1 d . . .
O3 O 0.51237(19) 1.1978(3) 0.01358(13) 0.0593(7) Uani 1 1 d . . .
O4 O 0.62267(19) 1.2957(2) 0.09628(12) 0.0508(6) Uani 1 1 d . . .
O5 O 0.6888(2) 1.3872(3) -0.03561(14) 0.0651(8) Uani 1 1 d . . .
O6 O 0.8775(2) 1.4203(3) -0.02451(15) 0.0664(8) 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 1.377(5) . ?
C1 C6 1.391(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.373(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(5) . ?
C3 Cl1 1.737(3) . ?
C4 C5 1.373(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.510(4) . ?
C7 C11 1.536(4) . ?
C7 C8 1.557(4) . ?
C7 H7 0.9800 . ?
C8 C10 1.475(4) . ?
C8 C9 1.481(4) . ?
C8 C15 1.579(4) . ?
C9 N1 1.129(4) . ?
C10 N2 1.132(4) . ?
C11 N3 1.468(4) . ?
C11 C12 1.520(4) . ?
C11 H11 0.9800 . ?
C12 O1 1.195(4) . ?
C12 O2 1.314(4) . ?
C13 O2 1.458(4) . ?
C13 C14 1.463(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N3 1.455(4) . ?
C15 C18 1.536(4) . ?
C15 C16 1.537(4) . ?
C16 O3 1.196(4) . ?
C16 O4 1.324(4) . ?
C17 O4 1.451(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.498(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 O5 1.193(4) . ?
C19 O6 1.315(4) . ?
C20 O6 1.446(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 Cl3 1.694(7) . ?
C21 Cl2 1.722(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
N3 H3 0.8600 . ?

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 121.3(3) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 Cl1 119.5(3) . . ?
C4 C3 Cl1 119.6(3) . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.2(3) . . ?
C1 C6 C7 118.7(3) . . ?
C5 C6 C7 123.2(3) . . ?
C6 C7 C11 117.8(2) . . ?
C6 C7 C8 115.3(2) . . ?
C11 C7 C8 101.5(2) . . ?
C6 C7 H7 107.2 . . ?
C11 C7 H7 107.2 . . ?
C8 C7 H7 107.2 . . ?
C10 C8 C9 108.4(2) . . ?
C10 C8 C7 110.9(2) . . ?
C9 C8 C7 110.9(2) . . ?
C10 C8 C15 115.0(2) . . ?
C9 C8 C15 110.0(2) . . ?
C7 C8 C15 101.5(2) . . ?
N1 C9 C8 178.3(4) . . ?
N2 C10 C8 178.4(4) . . ?
N3 C11 C12 109.7(2) . . ?
N3 C11 C7 105.4(2) . . ?
C12 C11 C7 110.3(2) . . ?
N3 C11 H11 110.4 . . ?
C12 C11 H11 110.4 . . ?
C7 C11 H11 110.4 . . ?
O1 C12 O2 123.7(3) . . ?
O1 C12 C11 124.6(3) . . ?
O2 C12 C11 111.8(2) . . ?
O2 C13 C14 108.8(3) . . ?
O2 C13 H13A 109.9 . . ?
C14 C13 H13A 109.9 . . ?
O2 C13 H13B 109.9 . . ?
C14 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 C18 111.5(2) . . ?
N3 C15 C16 109.7(2) . . ?
C18 C15 C16 111.4(2) . . ?
N3 C15 C8 103.8(2) . . ?
C18 C15 C8 110.3(2) . . ?
C16 C15 C8 109.9(2) . . ?
O3 C16 O4 125.2(3) . . ?
O3 C16 C15 124.0(3) . . ?
O4 C16 C15 110.6(2) . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C15 112.1(2) . . ?
C19 C18 H18A 109.2 . . ?
C15 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
C15 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
O5 C19 O6 124.1(3) . . ?
O5 C19 C18 125.4(3) . . ?
O6 C19 C18 110.5(3) . . ?
O6 C20 H20A 109.5 . . ?
O6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Cl3 C21 Cl2 112.4(3) . . ?
Cl3 C21 H21A 109.1 . . ?
Cl2 C21 H21A 109.1 . . ?
Cl3 C21 H21B 109.1 . . ?
Cl2 C21 H21B 109.1 . . ?
H21A C21 H21B 107.9 . . ?
C15 N3 C11 111.4(2) . . ?
C15 N3 H3 124.3 . . ?
C11 N3 H3 124.3 . . ?
C12 O2 C13 116.5(3) . . ?
C16 O4 C17 115.2(3) . . ?
C19 O6 C20 116.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.129
####################################################################### 
# 
# 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_3e
_database_code_depnum_ccdc_archive 'CCDC 1556667'
_audit_update_record             
;
2017-06-17 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 N3 O7'
_chemical_formula_sum            'C21 H23 N3 O7'
_chemical_formula_weight         429.42

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   11.771(4)
_cell_length_b                   10.369(3)
_cell_length_c                   20.983(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.310(10)
_cell_angle_gamma                90.00
_cell_volume                     2545.5(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      24.83

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39370
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         27.57
_reflns_number_total             5860
_reflns_number_gt                3730
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1526P)²+1.4100P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5860
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.0858
_refine_ls_wR_factor_ref         0.2940
_refine_ls_wR_factor_gt          0.2710
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7436(3) 0.7237(3) 0.07458(17) 0.0519(8) Uani 1 1 d . . .
H1 H 0.6744 0.7388 0.0498 0.062 Uiso 1 1 calc R . .
C2 C 0.7619(3) 0.6070(3) 0.10526(18) 0.0598(10) Uani 1 1 d . . .
H2 H 0.7045 0.5450 0.1016 0.072 Uiso 1 1 calc R . .
C3 C 0.8648(3) 0.5811(3) 0.14148(17) 0.0546(9) Uani 1 1 d . . .
C4 C 0.9695(4) 0.4361(4) 0.2136(2) 0.0704(11) Uani 1 1 d . . .
H4A H 1.0385 0.4368 0.1931 0.106 Uiso 1 1 calc R . .
H4B H 0.9599 0.3528 0.2323 0.106 Uiso 1 1 calc R . .
H4C H 0.9741 0.5007 0.2466 0.106 Uiso 1 1 calc R . .
C5 C 0.9484(3) 0.6756(3) 0.14706(18) 0.0545(9) Uani 1 1 d . . .
H5 H 1.0179 0.6603 0.1714 0.065 Uiso 1 1 calc R . .
C6 C 0.9282(3) 0.7927(3) 0.11641(16) 0.0476(8) Uani 1 1 d . . .
H6 H 0.9851 0.8554 0.1205 0.057 Uiso 1 1 calc R . .
C7 C 0.8263(2) 0.8190(3) 0.07999(14) 0.0401(7) Uani 1 1 d . . .
C8 C 0.8082(2) 0.9493(3) 0.04788(14) 0.0378(6) Uani 1 1 d . . .
H8 H 0.8837 0.9854 0.0431 0.045 Uiso 1 1 calc R . .
C9 C 0.7426(2) 1.0497(3) 0.08570(14) 0.0385(6) Uani 1 1 d . . .
C10 C 0.6356(3) 0.9961(3) 0.10518(14) 0.0459(7) Uani 1 1 d . . .
C11 C 0.8135(3) 1.0947(3) 0.14246(15) 0.0448(7) Uani 1 1 d . . .
C12 C 0.7385(2) 0.9534(3) -0.01771(14) 0.0397(7) Uani 1 1 d . . .
H12 H 0.6726 0.8953 -0.0186 0.048 Uiso 1 1 calc R . .
C13 C 0.8124(3) 0.9166(3) -0.07056(15) 0.0439(7) Uani 1 1 d . . .
C14 C 0.8100(4) 0.8290(5) -0.1751(2) 0.0801(13) Uani 1 1 d . . .
H14A H 0.8302 0.9082 -0.1957 0.096 Uiso 1 1 calc R . .
H14B H 0.8795 0.7809 -0.1624 0.096 Uiso 1 1 calc R . .
C15 C 0.7342(5) 0.7540(7) -0.2184(2) 0.111(2) Uani 1 1 d . . .
H15A H 0.7000 0.6875 -0.1951 0.166 Uiso 1 1 calc R . .
H15B H 0.7763 0.7155 -0.2502 0.166 Uiso 1 1 calc R . .
H15C H 0.6755 0.8087 -0.2391 0.166 Uiso 1 1 calc R . .
C16 C 0.7140(2) 1.1583(3) 0.03276(14) 0.0382(6) Uani 1 1 d . . .
C17 C 0.6000(2) 1.2248(3) 0.04430(15) 0.0423(7) Uani 1 1 d . . .
C18 C 0.5099(4) 1.3639(5) 0.1100(3) 0.0889(14) Uani 1 1 d . . .
H18A H 0.4908 1.4330 0.0803 0.133 Uiso 1 1 calc R . .
H18B H 0.5223 1.3979 0.1528 0.133 Uiso 1 1 calc R . .
H18C H 0.4482 1.3029 0.1073 0.133 Uiso 1 1 calc R . .
C19 C 0.8114(2) 1.2569(3) 0.03494(16) 0.0466(7) Uani 1 1 d . . .
H19A H 0.8263 1.2913 0.0780 0.056 Uiso 1 1 calc R . .
H19B H 0.8803 1.2143 0.0245 0.056 Uiso 1 1 calc R . .
C20 C 0.7830(3) 1.3649(3) -0.01084(16) 0.0475(7) Uani 1 1 d . . .
C21 C 0.8611(5) 1.5452(5) -0.0597(3) 0.0946(15) Uani 1 1 d . . .
H21A H 0.8195 1.5239 -0.1003 0.142 Uiso 1 1 calc R . .
H21B H 0.9342 1.5806 -0.0665 0.142 Uiso 1 1 calc R . .
H21C H 0.8187 1.6076 -0.0381 0.142 Uiso 1 1 calc R . .
N1 N 0.5516(3) 0.9565(3) 0.11887(17) 0.0713(9) Uani 1 1 d . . .
N2 N 0.8717(3) 1.1273(3) 0.18664(16) 0.0709(9) Uani 1 1 d . . .
N3 N 0.6998(2) 1.0873(2) -0.02650(12) 0.0471(6) Uani 1 1 d . . .
H3 H 0.6719 1.1194 -0.0627 0.056 Uiso 1 1 calc R . .
O1 O 0.8751(3) 0.4625(2) 0.16776(14) 0.0780(9) Uani 1 1 d . . .
O2 O 0.9118(2) 0.9366(4) -0.06837(14) 0.0863(10) Uani 1 1 d . . .
O3 O 0.75096(19) 0.8591(2) -0.11788(11) 0.0572(6) Uani 1 1 d . . .
O4 O 0.51187(18) 1.2031(3) 0.01212(13) 0.0635(7) Uani 1 1 d . . .
O5 O 0.61324(18) 1.3002(2) 0.09426(11) 0.0535(6) Uani 1 1 d . . .
O6 O 0.6896(2) 1.3927(3) -0.03451(14) 0.0712(8) Uani 1 1 d . . .
O7 O 0.8775(2) 1.4300(3) -0.02077(14) 0.0710(8) 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 1.377(5) . ?
C1 C7 1.383(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.384(5) . ?
C2 H2 0.9300 . ?
C3 O1 1.348(4) . ?
C3 C5 1.384(5) . ?
C4 O1 1.415(5) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.382(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.514(4) . ?
C8 C12 1.523(4) . ?
C8 C9 1.564(4) . ?
C8 H8 0.9800 . ?
C9 C11 1.454(4) . ?
C9 C10 1.475(4) . ?
C9 C16 1.592(4) . ?
C10 N1 1.136(4) . ?
C11 N2 1.142(4) . ?
C12 N3 1.467(4) . ?
C12 C13 1.531(4) . ?
C12 H12 0.9800 . ?
C13 O2 1.184(4) . ?
C13 O3 1.306(4) . ?
C14 C15 1.431(7) . ?
C14 O3 1.485(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N3 1.439(4) . ?
C16 C19 1.533(4) . ?
C16 C17 1.550(4) . ?
C17 O4 1.196(3) . ?
C17 O5 1.303(4) . ?
C18 O5 1.454(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.489(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 O6 1.190(4) . ?
C20 O7 1.337(4) . ?
C21 O7 1.448(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N3 H3 0.8600 . ?

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 C7 121.2(3) . . ?
C2 C1 H1 119.4 . . ?
C7 C1 H1 119.4 . . ?
C1 C2 C3 120.7(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O1 C3 C2 115.9(3) . . ?
O1 C3 C5 125.4(3) . . ?
C2 C3 C5 118.7(3) . . ?
O1 C4 H4A 109.5 . . ?
O1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C3 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
C3 C5 H5 120.1 . . ?
C7 C6 C5 121.8(3) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C1 117.8(3) . . ?
C6 C7 C8 119.7(2) . . ?
C1 C7 C8 122.5(3) . . ?
C7 C8 C12 117.6(2) . . ?
C7 C8 C9 115.0(2) . . ?
C12 C8 C9 101.1(2) . . ?
C7 C8 H8 107.5 . . ?
C12 C8 H8 107.5 . . ?
C9 C8 H8 107.5 . . ?
C11 C9 C10 108.9(3) . . ?
C11 C9 C8 111.0(2) . . ?
C10 C9 C8 111.9(2) . . ?
C11 C9 C16 113.8(2) . . ?
C10 C9 C16 109.8(2) . . ?
C8 C9 C16 101.3(2) . . ?
N1 C10 C9 178.2(4) . . ?
N2 C11 C9 177.9(4) . . ?
N3 C12 C8 105.6(2) . . ?
N3 C12 C13 109.8(2) . . ?
C8 C12 C13 110.8(2) . . ?
N3 C12 H12 110.2 . . ?
C8 C12 H12 110.2 . . ?
C13 C12 H12 110.2 . . ?
O2 C13 O3 124.8(3) . . ?
O2 C13 C12 124.5(3) . . ?
O3 C13 C12 110.7(2) . . ?
C15 C14 O3 108.3(4) . . ?
C15 C14 H14A 110.0 . . ?
O3 C14 H14A 110.0 . . ?
C15 C14 H14B 110.0 . . ?
O3 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C19 112.5(3) . . ?
N3 C16 C17 110.0(2) . . ?
C19 C16 C17 110.8(2) . . ?
N3 C16 C9 103.7(2) . . ?
C19 C16 C9 110.5(2) . . ?
C17 C16 C9 109.0(2) . . ?
O4 C17 O5 125.9(3) . . ?
O4 C17 C16 122.7(3) . . ?
O5 C17 C16 111.3(2) . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C16 111.6(2) . . ?
C20 C19 H19A 109.3 . . ?
C16 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C16 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
O6 C20 O7 124.0(3) . . ?
O6 C20 C19 125.6(3) . . ?
O7 C20 C19 110.4(3) . . ?
O7 C21 H21A 109.5 . . ?
O7 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O7 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 N3 C12 111.8(2) . . ?
C16 N3 H3 124.1 . . ?
C12 N3 H3 124.1 . . ?
C3 O1 C4 119.0(3) . . ?
C13 O3 C14 116.2(3) . . ?
C17 O5 C18 115.2(3) . . ?
C20 O7 C21 116.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.102


loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 -0.017 0.750 260 92 ' '
2 0.500 -0.027 0.250 260 92 ' '
_platon_squeeze_details          
; 
;
####################################################################### 
# 
# 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_4f
_database_code_depnum_ccdc_archive 'CCDC 1556670'
_audit_update_record             
;
2017-06-17 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H25 N3 O10'
_chemical_formula_sum            'C22 H25 N3 O10'
_chemical_formula_weight         491.45

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2529(11)
_cell_length_b                   10.4792(14)
_cell_length_c                   14.724(2)
_cell_angle_alpha                90.680(5)
_cell_angle_beta                 97.661(5)
_cell_angle_gamma                108.073(4)
_cell_volume                     1197.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7884
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.32

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17025
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_av_sigmaI/netI    0.0703
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.40
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5464
_reflns_number_gt                3894
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1092P)²+0.5105P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5464
_refine_ls_number_parameters     324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0699
_refine_ls_wR_factor_ref         0.2114
_refine_ls_wR_factor_gt          0.1890
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4036(2) -0.0618(2) 0.31200(14) 0.0320(4) Uani 1 1 d . . .
H1 H 0.4412 -0.0309 0.2571 0.038 Uiso 1 1 calc R . .
C2 C 0.4994(3) -0.1197(2) 0.37261(15) 0.0350(5) Uani 1 1 d . . .
C3 C 0.4500(3) -0.1665(2) 0.45528(16) 0.0409(5) Uani 1 1 d . . .
H3A H 0.5174 -0.2045 0.4948 0.049 Uiso 1 1 calc R . .
C4 C 0.2976(3) -0.1550(3) 0.47739(16) 0.0419(5) Uani 1 1 d . . .
H4 H 0.2613 -0.1857 0.5326 0.050 Uiso 1 1 calc R . .
C5 C 0.1988(3) -0.0981(2) 0.41815(14) 0.0359(5) Uani 1 1 d . . .
H5 H 0.0963 -0.0911 0.4339 0.043 Uiso 1 1 calc R . .
C6 C 0.2504(2) -0.0507(2) 0.33459(13) 0.0292(4) Uani 1 1 d . . .
C7 C 0.1408(2) 0.0140(2) 0.27265(13) 0.0293(4) Uani 1 1 d . . .
H7 H 0.0234 -0.0195 0.2878 0.035 Uiso 1 1 calc R . .
C8 C 0.1996(3) 0.1706(2) 0.28417(14) 0.0324(4) Uani 1 1 d . . .
C9 C 0.3886(3) 0.2267(2) 0.29470(15) 0.0389(5) Uani 1 1 d . . .
C10 C 0.1292(3) 0.2176(2) 0.36565(16) 0.0409(5) Uani 1 1 d . . .
C11 C 0.1630(6) 0.3956(5) 0.4725(3) 0.1063(15) Uani 1 1 d . . .
H11A H 0.0864 0.4401 0.4411 0.128 Uiso 1 1 calc R . .
H11B H 0.0957 0.3263 0.5078 0.128 Uiso 1 1 calc R . .
C12 C 0.2898(9) 0.4885(6) 0.5320(5) 0.164(3) Uani 1 1 d . . .
H12A H 0.3571 0.4433 0.5692 0.245 Uiso 1 1 calc R . .
H12B H 0.2373 0.5335 0.5708 0.245 Uiso 1 1 calc R . .
H12C H 0.3630 0.5533 0.4974 0.245 Uiso 1 1 calc R . .
C13 C 0.1201(3) 0.2078(2) 0.18771(15) 0.0354(5) Uani 1 1 d . . .
C14 C 0.2165(3) 0.3516(3) 0.16525(19) 0.0492(6) Uani 1 1 d . . .
C15 C 0.2555(6) 0.5800(4) 0.2004(5) 0.130(2) Uani 1 1 d . . .
H15A H 0.3752 0.6018 0.2248 0.196 Uiso 1 1 calc R . .
H15B H 0.2047 0.6353 0.2318 0.196 Uiso 1 1 calc R . .
H15C H 0.2443 0.5958 0.1361 0.196 Uiso 1 1 calc R . .
C16 C -0.0738(3) 0.1886(2) 0.18586(15) 0.0384(5) Uani 1 1 d . . .
H16A H -0.1302 0.0991 0.2046 0.046 Uiso 1 1 calc R . .
H16B H -0.0871 0.2530 0.2298 0.046 Uiso 1 1 calc R . .
C17 C -0.1606(3) 0.2064(3) 0.09256(17) 0.0456(6) Uani 1 1 d . . .
C18 C -0.4330(4) 0.1906(5) 0.0108(3) 0.0961(14) Uani 1 1 d . . .
H18A H -0.3926 0.2833 -0.0035 0.144 Uiso 1 1 calc R . .
H18B H -0.5510 0.1676 0.0208 0.144 Uiso 1 1 calc R . .
H18C H -0.4243 0.1349 -0.0393 0.144 Uiso 1 1 calc R . .
C19 C 0.1301(3) -0.0150(2) 0.16798(14) 0.0339(5) Uani 1 1 d . . .
H19 H 0.2225 -0.0514 0.1576 0.041 Uiso 1 1 calc R . .
C20 C -0.0430(3) -0.1178(2) 0.13005(14) 0.0379(5) Uani 1 1 d . . .
C21 C -0.2184(4) -0.3428(3) 0.1333(3) 0.0750(9) Uani 1 1 d . . .
H21A H -0.3163 -0.3132 0.1409 0.090 Uiso 1 1 calc R . .
H21B H -0.2244 -0.3662 0.0688 0.090 Uiso 1 1 calc R . .
C22 C -0.2220(6) -0.4566(5) 0.1860(5) 0.148(3) Uani 1 1 d . . .
H22A H -0.1212 -0.4820 0.1810 0.222 Uiso 1 1 calc R . .
H22B H -0.3230 -0.5301 0.1632 0.222 Uiso 1 1 calc R . .
H22C H -0.2242 -0.4344 0.2491 0.222 Uiso 1 1 calc R . .
N1 N 0.6610(2) -0.1299(2) 0.34786(16) 0.0478(5) Uani 1 1 d . . .
N2 N 0.5351(3) 0.2656(2) 0.30508(17) 0.0574(6) Uani 1 1 d . . .
N3 N 0.1622(2) 0.1146(2) 0.12931(13) 0.0394(4) Uani 1 1 d . . .
O1 O 0.6905(2) -0.1094(2) 0.26925(15) 0.0656(6) Uani 1 1 d . . .
O2 O 0.7603(3) -0.1581(3) 0.40729(18) 0.0842(8) Uani 1 1 d . . .
O3 O -0.0053(3) 0.1568(2) 0.38870(13) 0.0572(5) Uani 1 1 d . . .
O4 O 0.2317(3) 0.3324(2) 0.40420(16) 0.0697(6) Uani 1 1 d . . .
O5 O 0.3217(3) 0.3814(2) 0.11448(16) 0.0742(7) Uani 1 1 d . . .
O6 O 0.1681(3) 0.4397(2) 0.21304(19) 0.0763(7) Uani 1 1 d . . .
O7 O -0.0906(3) 0.2482(3) 0.02796(14) 0.0716(7) Uani 1 1 d . . .
O8 O -0.3300(2) 0.1698(2) 0.09214(14) 0.0661(6) Uani 1 1 d . . .
O9 O -0.1495(2) -0.09397(19) 0.07553(12) 0.0512(5) Uani 1 1 d . . .
O10 O -0.0576(2) -0.23506(17) 0.16530(12) 0.0516(5) Uani 1 1 d . . .
H3B H 0.127(4) 0.117(3) 0.067(2) 0.059(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 1.383(3) . ?
C1 C6 1.388(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(3) . ?
C2 N1 1.462(3) . ?
C3 C4 1.380(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.402(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.512(3) . ?
C7 C19 1.553(3) . ?
C7 C8 1.561(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.473(3) . ?
C8 C10 1.539(3) . ?
C8 C13 1.588(3) . ?
C9 N2 1.138(3) . ?
C10 O3 1.192(3) . ?
C10 O4 1.308(3) . ?
C11 C12 1.383(7) . ?
C11 O4 1.463(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N3 1.443(3) . ?
C13 C14 1.534(3) . ?
C13 C16 1.546(3) . ?
C14 O5 1.192(3) . ?
C14 O6 1.340(4) . ?
C15 O6 1.450(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.504(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O7 1.196(3) . ?
C17 O8 1.330(3) . ?
C18 O8 1.433(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 N3 1.441(3) . ?
C19 C20 1.527(3) . ?
C19 H19 0.9800 . ?
C20 O9 1.197(3) . ?
C20 O10 1.316(3) . ?
C21 C22 1.425(6) . ?
C21 O10 1.466(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 O2 1.221(3) . ?
N1 O1 1.222(3) . ?
N3 H3B 0.92(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
C2 C1 C6 118.78(19) . . ?
C2 C1 H1 120.6 . . ?
C6 C1 H1 120.6 . . ?
C3 C2 C1 122.92(19) . . ?
C3 C2 N1 119.08(19) . . ?
C1 C2 N1 118.00(19) . . ?
C4 C3 C2 118.01(19) . . ?
C4 C3 H3A 121.0 . . ?
C2 C3 H3A 121.0 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 121.06(19) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.80(18) . . ?
C1 C6 C7 121.73(17) . . ?
C5 C6 C7 119.45(17) . . ?
C6 C7 C19 115.91(16) . . ?
C6 C7 C8 114.37(16) . . ?
C19 C7 C8 103.85(15) . . ?
C6 C7 H7 107.4 . . ?
C19 C7 H7 107.4 . . ?
C8 C7 H7 107.4 . . ?
C9 C8 C10 110.95(18) . . ?
C9 C8 C7 110.78(17) . . ?
C10 C8 C7 111.05(17) . . ?
C9 C8 C13 109.11(17) . . ?
C10 C8 C13 113.21(17) . . ?
C7 C8 C13 101.38(15) . . ?
N2 C9 C8 177.1(3) . . ?
O3 C10 O4 124.7(2) . . ?
O3 C10 C8 123.2(2) . . ?
O4 C10 C8 112.1(2) . . ?
C12 C11 O4 113.2(4) . . ?
C12 C11 H11A 108.9 . . ?
O4 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
O4 C11 H11B 108.9 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 108.82(19) . . ?
N3 C13 C16 116.15(19) . . ?
C14 C13 C16 110.69(18) . . ?
N3 C13 C8 98.80(16) . . ?
C14 C13 C8 111.54(18) . . ?
C16 C13 C8 110.34(16) . . ?
O5 C14 O6 124.8(3) . . ?
O5 C14 C13 125.3(3) . . ?
O6 C14 C13 109.9(2) . . ?
O6 C15 H15A 109.5 . . ?
O6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C13 112.63(18) . . ?
C17 C16 H16A 109.1 . . ?
C13 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C13 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
O7 C17 O8 124.1(2) . . ?
O7 C17 C16 126.3(2) . . ?
O8 C17 C16 109.6(2) . . ?
O8 C18 H18A 109.5 . . ?
O8 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O8 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C20 114.76(18) . . ?
N3 C19 C7 104.86(17) . . ?
C20 C19 C7 110.46(16) . . ?
N3 C19 H19 108.9 . . ?
C20 C19 H19 108.9 . . ?
C7 C19 H19 108.9 . . ?
O9 C20 O10 125.2(2) . . ?
O9 C20 C19 124.1(2) . . ?
O10 C20 C19 110.68(18) . . ?
C22 C21 O10 108.4(3) . . ?
C22 C21 H21A 110.0 . . ?
O10 C21 H21A 110.0 . . ?
C22 C21 H21B 110.0 . . ?
O10 C21 H21B 110.0 . . ?
H21A C21 H21B 108.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 N1 O1 123.2(2) . . ?
O2 N1 C2 118.0(2) . . ?
O1 N1 C2 118.75(19) . . ?
C19 N3 C13 111.04(17) . . ?
C19 N3 H3B 118.1(19) . . ?
C13 N3 H3B 115.1(19) . . ?
C10 O4 C11 115.9(3) . . ?
C14 O6 C15 115.2(3) . . ?
C17 O8 C18 117.4(2) . . ?
C20 O10 C21 115.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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_4d
_database_code_depnum_ccdc_archive 'CCDC 1556669'
_audit_update_record             
;
2017-06-17 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H25 Cl N2 O8'
_chemical_formula_sum            'C22 H25 Cl N2 O8'
_chemical_formula_weight         480.89

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   20.981(3)
_cell_length_b                   11.5804(17)
_cell_length_c                   20.012(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.351(5)
_cell_angle_gamma                90.00
_cell_volume                     4783.2(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9938
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      26.99

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2016
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35268
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         27.57
_reflns_number_total             5503
_reflns_number_gt                4030
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0732P)²+4.8772P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0069(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5503
_refine_ls_number_parameters     307
_refine_ls_number_restraints     462
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1647
_refine_ls_wR_factor_gt          0.1489
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.118
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.14821(13) 0.6998(2) 0.29295(14) 0.0578(6) Uani 1 1 d U . .
H1 H 0.1865 0.6858 0.2769 0.069 Uiso 1 1 calc R . .
C2 C 0.13586(16) 0.8100(2) 0.31466(17) 0.0725(8) Uani 1 1 d U . .
H2A H 0.1654 0.8694 0.3131 0.087 Uiso 1 1 calc R . .
C3 C 0.07943(15) 0.8301(2) 0.33854(16) 0.0655(7) Uani 1 1 d U . .
C4 C 0.03613(13) 0.7428(2) 0.34214(14) 0.0570(6) Uani 1 1 d U . .
H4 H -0.0016 0.7571 0.3590 0.068 Uiso 1 1 calc R . .
C5 C 0.04895(11) 0.6340(2) 0.32072(12) 0.0458(5) Uani 1 1 d U . .
H5 H 0.0197 0.5747 0.3237 0.055 Uiso 1 1 calc R . .
C6 C 0.10487(10) 0.61043(18) 0.29460(10) 0.0378(5) Uani 1 1 d U . .
C7 C 0.11522(9) 0.48758(18) 0.27219(10) 0.0337(4) Uani 1 1 d U . .
H7 H 0.0734 0.4591 0.2479 0.040 Uiso 1 1 calc R . .
C8 C 0.13815(9) 0.40370(18) 0.33255(9) 0.0344(4) Uani 1 1 d U . .
C9 C 0.19053(10) 0.4593(2) 0.38099(10) 0.0403(5) Uani 1 1 d U . .
C10 C 0.08218(10) 0.36721(19) 0.36811(10) 0.0381(5) Uani 1 1 d U . .
C11 C 0.05045(15) 0.3345(3) 0.47431(14) 0.0693(8) Uani 1 1 d U . .
H11A H 0.0569 0.3774 0.5166 0.083 Uiso 1 1 calc R . .
H11B H 0.0079 0.3535 0.4490 0.083 Uiso 1 1 calc R . .
C12 C 0.0536(3) 0.2138(4) 0.4886(3) 0.148(2) Uani 1 1 d U . .
H12A H 0.0504 0.1714 0.4469 0.222 Uiso 1 1 calc R . .
H12B H 0.0185 0.1925 0.5110 0.222 Uiso 1 1 calc R . .
H12C H 0.0941 0.1962 0.5176 0.222 Uiso 1 1 calc R . .
C13 C 0.16893(9) 0.30195(19) 0.29532(10) 0.0371(5) Uani 1 1 d U . .
C14 C 0.21718(11) 0.2329(2) 0.34644(11) 0.0464(5) Uani 1 1 d U . .
C15 C 0.22511(18) 0.1027(3) 0.43816(17) 0.0897(11) Uani 1 1 d U . .
H15A H 0.2413 0.0364 0.4178 0.135 Uiso 1 1 calc R . .
H15B H 0.1992 0.0779 0.4704 0.135 Uiso 1 1 calc R . .
H15C H 0.2608 0.1481 0.4609 0.135 Uiso 1 1 calc R . .
C16 C 0.11557(10) 0.22405(19) 0.25648(11) 0.0427(5) Uani 1 1 d U . .
H16A H 0.0900 0.1930 0.2882 0.051 Uiso 1 1 calc R . .
H16B H 0.0871 0.2703 0.2234 0.051 Uiso 1 1 calc R . .
C17 C 0.14180(11) 0.1259(2) 0.22063(13) 0.0496(6) Uani 1 1 d U . .
C18 C 0.11598(18) -0.0051(4) 0.1301(2) 0.1054(15) Uani 1 1 d U . .
H18A H 0.1563 0.0072 0.1148 0.158 Uiso 1 1 calc R . .
H18B H 0.0823 -0.0193 0.0917 0.158 Uiso 1 1 calc R . .
H18C H 0.1200 -0.0705 0.1601 0.158 Uiso 1 1 calc R . .
C19 C 0.16602(10) 0.46660(19) 0.22549(10) 0.0369(4) Uani 1 1 d U . .
H19 H 0.1961 0.5321 0.2306 0.044 Uiso 1 1 calc R . .
C20 C 0.13325(11) 0.4593(2) 0.15133(10) 0.0431(5) Uani 1 1 d U . .
C21 C 0.14085(17) 0.3776(3) 0.04411(13) 0.0778(9) Uani 1 1 d U . .
H21A H 0.0939 0.3739 0.0361 0.093 Uiso 1 1 calc R . .
H21B H 0.1535 0.4428 0.0190 0.093 Uiso 1 1 calc R . .
C22 C 0.1656(4) 0.2768(5) 0.0221(2) 0.172(3) Uani 1 1 d U . .
H22A H 0.2117 0.2753 0.0368 0.259 Uiso 1 1 calc R . .
H22B H 0.1557 0.2734 -0.0266 0.259 Uiso 1 1 calc R . .
H22C H 0.1466 0.2117 0.0408 0.259 Uiso 1 1 calc R . .
Cl1 Cl 0.06294(7) 0.96843(8) 0.36505(8) 0.1249(5) Uani 1 1 d . . .
N1 N 0.23165(10) 0.5039(2) 0.41598(10) 0.0599(6) Uani 1 1 d . . .
N2 N 0.20264(9) 0.36247(18) 0.24895(9) 0.0421(4) Uani 1 1 d . . .
O1 O 0.02987(7) 0.34237(16) 0.33762(9) 0.0536(4) Uani 1 1 d . . .
O2 O 0.09979(8) 0.36817(17) 0.43493(8) 0.0549(5) Uani 1 1 d . . .
O3 O 0.27464(8) 0.23832(19) 0.35158(10) 0.0680(6) Uani 1 1 d . . .
O4 O 0.18581(8) 0.17167(16) 0.38588(9) 0.0597(5) Uani 1 1 d . . .
O5 O 0.19187(9) 0.07671(17) 0.23962(11) 0.0697(6) Uani 1 1 d . . .
O6 O 0.09998(9) 0.09654(19) 0.16597(11) 0.0764(7) Uani 1 1 d . . .
O7 O 0.08522(9) 0.5110(2) 0.12790(9) 0.0713(6) Uani 1 1 d . . .
O8 O 0.16554(9) 0.39270(19) 0.11628(8) 0.0666(6) Uani 1 1 d . . .
H2B H 0.2382(13) 0.380(2) 0.2685(13) 0.052(7) 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 C6 1.382(3) . ?
C1 C2 1.387(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.369(4) . ?
C3 Cl1 1.742(3) . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.519(3) . ?
C7 C8 1.557(3) . ?
C7 C19 1.558(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.476(3) . ?
C8 C10 1.537(3) . ?
C8 C13 1.592(3) . ?
C9 N1 1.134(3) . ?
C10 O1 1.191(3) . ?
C10 O2 1.322(3) . ?
C11 C12 1.426(5) . ?
C11 O2 1.462(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N2 1.445(3) . ?
C13 C14 1.529(3) . ?
C13 C16 1.536(3) . ?
C14 O3 1.193(3) . ?
C14 O4 1.321(3) . ?
C15 O4 1.450(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.500(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O5 1.196(3) . ?
C17 O6 1.318(3) . ?
C18 O6 1.449(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 N2 1.461(3) . ?
C19 C20 1.522(3) . ?
C19 H19 0.9800 . ?
C20 O7 1.193(3) . ?
C20 O8 1.310(3) . ?
C21 C22 1.381(6) . ?
C21 O8 1.455(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N2 H2B 0.80(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 121.4(2) . . ?
C6 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 Cl1 119.5(2) . . ?
C2 C3 Cl1 119.5(2) . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 117.7(2) . . ?
C1 C6 C7 124.39(19) . . ?
C5 C6 C7 117.92(18) . . ?
C6 C7 C8 113.32(16) . . ?
C6 C7 C19 118.21(17) . . ?
C8 C7 C19 102.64(15) . . ?
C6 C7 H7 107.4 . . ?
C8 C7 H7 107.4 . . ?
C19 C7 H7 107.4 . . ?
C9 C8 C10 110.88(16) . . ?
C9 C8 C7 109.09(17) . . ?
C10 C8 C7 112.04(15) . . ?
C9 C8 C13 108.26(16) . . ?
C10 C8 C13 114.90(17) . . ?
C7 C8 C13 101.16(15) . . ?
N1 C9 C8 177.2(2) . . ?
O1 C10 O2 125.77(19) . . ?
O1 C10 C8 122.64(19) . . ?
O2 C10 C8 111.60(17) . . ?
C12 C11 O2 111.0(3) . . ?
C12 C11 H11A 109.4 . . ?
O2 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
O2 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 109.97(17) . . ?
N2 C13 C16 110.88(17) . . ?
C14 C13 C16 111.50(18) . . ?
N2 C13 C8 103.18(17) . . ?
C14 C13 C8 110.44(16) . . ?
C16 C13 C8 110.58(15) . . ?
O3 C14 O4 125.5(2) . . ?
O3 C14 C13 124.6(2) . . ?
O4 C14 C13 109.83(18) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C13 112.96(17) . . ?
C17 C16 H16A 109.0 . . ?
C13 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C13 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
O5 C17 O6 123.8(2) . . ?
O5 C17 C16 125.9(2) . . ?
O6 C17 C16 110.23(19) . . ?
O6 C18 H18A 109.5 . . ?
O6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 C20 112.78(18) . . ?
N2 C19 C7 108.23(16) . . ?
C20 C19 C7 110.84(16) . . ?
N2 C19 H19 108.3 . . ?
C20 C19 H19 108.3 . . ?
C7 C19 H19 108.3 . . ?
O7 C20 O8 124.5(2) . . ?
O7 C20 C19 123.9(2) . . ?
O8 C20 C19 111.60(19) . . ?
C22 C21 O8 109.3(3) . . ?
C22 C21 H21A 109.8 . . ?
O8 C21 H21A 109.8 . . ?
C22 C21 H21B 109.8 . . ?
O8 C21 H21B 109.8 . . ?
H21A C21 H21B 108.3 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C13 N2 C19 108.48(16) . . ?
C13 N2 H2B 109.1(19) . . ?
C19 N2 H2B 109.8(19) . . ?
C10 O2 C11 116.54(19) . . ?
C14 O4 C15 116.6(2) . . ?
C17 O6 C18 116.2(2) . . ?
C20 O8 C21 118.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_2h
_database_code_depnum_ccdc_archive 'CCDC 1559439'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 Br N3 O5, C2 H6 O '
_chemical_formula_sum            'C21 H22 Br N3 O6'
_chemical_formula_weight         492.32

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'
Br Br -0.2901 2.4595 '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                   9.4419(10)
_cell_length_b                   10.4165(11)
_cell_length_c                   12.7123(12)
_cell_angle_alpha                80.387(3)
_cell_angle_beta                 71.426(3)
_cell_angle_gamma                76.536(3)
_cell_volume                     1146.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4971
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      24.72

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.833
_shelx_estimated_absorpt_T_min   0.667
_shelx_estimated_absorpt_T_max   0.711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.651
_exptl_absorpt_correction_T_max  0.693
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15828
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.319
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4474
_reflns_number_gt                2566
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1143P)²+1.4757P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4474
_refine_ls_number_parameters     290
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1304
_refine_ls_R_factor_gt           0.0735
_refine_ls_wR_factor_ref         0.2324
_refine_ls_wR_factor_gt          0.1969
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.042
_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
Br1 Br 0.67178(9) 0.79914(8) -0.02012(6) 0.1095(4) Uani 1 1 d . . . A 1
C1 C 0.2722(6) 0.7473(5) 0.2227(4) 0.0636(14) Uani 1 1 d . . . A 1
H1 H 0.1858 0.8018 0.2630 0.076 Uiso 1 1 calc R U . A 1
C2 C 0.3873(8) 0.8028(6) 0.1453(5) 0.0774(18) Uani 1 1 d . . . A 1
H2 H 0.3781 0.8945 0.1331 0.093 Uiso 1 1 calc R U . A 1
C3 C 0.5146(6) 0.7230(6) 0.0867(4) 0.0610(14) Uani 1 1 d . . . A 1
C4 C 0.5295(6) 0.5890(6) 0.1021(4) 0.0643(14) Uani 1 1 d . . . A 1
H4 H 0.6162 0.5349 0.0617 0.077 Uiso 1 1 calc R U . A 1
C5 C 0.4122(6) 0.5345(5) 0.1799(4) 0.0579(13) Uani 1 1 d . . . A 1
H5 H 0.4208 0.4428 0.1907 0.069 Uiso 1 1 calc R U . A 1
C6 C 0.2852(5) 0.6121(4) 0.2405(3) 0.0422(10) Uani 1 1 d . . . A 1
C7 C 0.1565(5) 0.5512(5) 0.3259(4) 0.0455(11) Uani 1 1 d . . . A 1
H7 H 0.0730 0.6240 0.3547 0.055 Uiso 1 1 calc R U . A 1
C8 C 0.0960(5) 0.4639(5) 0.2732(4) 0.0455(11) Uani 1 1 d . . . A 1
C9 C 0.0292(6) 0.5250(5) 0.1875(4) 0.0580(13) Uani 1 1 d . . . A 1
C10 C 0.1091(5) 0.3336(5) 0.3027(4) 0.0453(11) Uani 1 1 d . . . A 1
C11 C 0.2979(9) 0.0190(7) 0.3950(9) 0.109(4) Uani 0.849(11) 1 d D . P B 1
H11A H 0.3690 0.0325 0.3228 0.164 Uiso 0.849(11) 1 calc R U P B 1
H11B H 0.2696 -0.0657 0.4032 0.164 Uiso 0.849(11) 1 calc R U P B 1
H11C H 0.3442 0.0213 0.4517 0.164 Uiso 0.849(11) 1 calc R U P B 1
C11' C 0.145(6) 0.039(4) 0.516(2) 0.109(4) Uani 0.151(11) 1 d D . P B 2
H11D H 0.2386 0.0265 0.5354 0.164 Uiso 0.151(11) 1 calc R U P B 2
H11E H 0.1284 -0.0458 0.5078 0.164 Uiso 0.151(11) 1 calc R U P B 2
H11F H 0.0623 0.0793 0.5744 0.164 Uiso 0.151(11) 1 calc R U P B 2
C12 C 0.1569(7) 0.1280(5) 0.4068(6) 0.0780(18) Uani 1 1 d D . . . .
H12A H 0.0893 0.1178 0.4830 0.094 Uiso 0.849(11) 1 calc R U P B 1
H12B H 0.2582 0.0848 0.3644 0.094 Uiso 0.151(11) 1 calc R U P B 2
C13 C 0.0727(7) 0.1212(6) 0.3270(6) 0.0738(17) Uani 1 1 d . . . . .
C14 C 0.2214(5) 0.3408(5) 0.4441(4) 0.0455(11) Uani 1 1 d . . . . .
C15 C 0.2908(7) 0.2566(6) 0.5305(5) 0.0602(14) Uani 1 1 d . . . . .
C16 C 0.2499(13) 0.1643(11) 0.7154(7) 0.159(5) Uani 1 1 d . . . . .
H16A H 0.3386 0.1943 0.7154 0.238 Uiso 1 1 calc R U . . .
H16B H 0.2767 0.0724 0.7024 0.238 Uiso 1 1 calc R U . . .
H16C H 0.1741 0.1750 0.7863 0.238 Uiso 1 1 calc R U . . .
C17 C 0.2072(5) 0.4725(5) 0.4237(4) 0.0449(11) Uani 1 1 d . . . . .
C18 C 0.2345(5) 0.5557(6) 0.4959(4) 0.0517(13) Uani 1 1 d . . . . .
C19 C 0.3400(7) 0.5582(8) 0.6404(5) 0.085(2) Uani 1 1 d . . . . .
H19A H 0.3940 0.6272 0.5997 0.128 Uiso 1 1 calc R U . . .
H19B H 0.3999 0.4982 0.6831 0.128 Uiso 1 1 calc R U . . .
H19C H 0.2447 0.5967 0.6899 0.128 Uiso 1 1 calc R U . . .
N1 N -0.0174(7) 0.5778(6) 0.1165(5) 0.0904(17) Uani 1 1 d . . . . .
N2 N 0.0560(5) 0.2416(4) 0.2660(3) 0.0548(11) Uani 1 1 d . . . . .
H2A H 0.0172 0.2582 0.2114 0.066 Uiso 1 1 calc R U . A 1
N3 N 0.1805(4) 0.2671(4) 0.3803(3) 0.0506(10) Uani 1 1 d . . . . .
O1 O 0.0281(7) 0.0245(4) 0.3166(5) 0.1116(19) Uani 1 1 d . . . . .
O2 O 0.4234(5) 0.2052(4) 0.5077(4) 0.0838(13) Uani 1 1 d . . . . .
O3 O 0.1891(5) 0.2426(4) 0.6271(3) 0.0807(12) Uani 1 1 d . . . . .
O4 O 0.1878(5) 0.6732(4) 0.4941(3) 0.0704(11) Uani 1 1 d . . . . .
O5 O 0.3124(4) 0.4873(4) 0.5639(3) 0.0703(11) Uani 1 1 d . . . . .
O1S O 0.9058(8) 0.2922(7) 0.1052(5) 0.1229(16) Uani 1 1 d . U . . .
H1S H 0.9219 0.3504 0.0533 0.184 Uiso 1 1 calc R U . . .
C1S C 0.8618(10) 0.1886(10) 0.0709(8) 0.1321(17) Uani 1 1 d D U . . .
H1S1 H 0.9311 0.1054 0.0795 0.159 Uiso 1 1 calc R U . . .
H1S2 H 0.8641 0.2077 -0.0069 0.159 Uiso 1 1 calc R U . . .
C2S C 0.7026(10) 0.1792(11) 0.1433(8) 0.1410(19) Uani 1 1 d D U . . .
H2S1 H 0.6698 0.1094 0.1220 0.211 Uiso 1 1 calc R U . . .
H2S2 H 0.6350 0.2618 0.1338 0.211 Uiso 1 1 calc R U . . .
H2S3 H 0.7017 0.1603 0.2200 0.211 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.892(5) . ?
C1 C6 1.372(7) . ?
C1 C2 1.380(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.365(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(8) . ?
C4 C5 1.390(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.361(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.531(6) . ?
C7 C8 1.514(7) . ?
C7 C17 1.518(6) . ?
C7 H7 0.9800 . ?
C8 C10 1.334(7) . ?
C8 C9 1.418(7) . ?
C9 N1 1.133(7) . ?
C10 N3 1.373(6) . ?
C10 N2 1.382(6) . ?
C11 C12 1.520(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11' C12 1.527(5) . ?
C11' H11D 0.9600 . ?
C11' H11E 0.9600 . ?
C11' H11F 0.9600 . ?
C12 N3 1.484(7) . ?
C12 C13 1.493(9) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 O1 1.219(7) . ?
C13 N2 1.364(7) . ?
C14 C17 1.335(7) . ?
C14 N3 1.394(6) . ?
C14 C15 1.508(7) . ?
C15 O2 1.203(6) . ?
C15 O3 1.306(7) . ?
C16 O3 1.463(8) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.476(7) . ?
C18 O4 1.200(6) . ?
C18 O5 1.323(6) . ?
C19 O5 1.433(7) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N2 H2A 0.8600 . ?
O1S C1S 1.416(9) . ?
O1S H1S 0.8200 . ?
C1S C2S 1.508(5) . ?
C1S H1S1 0.9700 . ?
C1S H1S2 0.9700 . ?
C2S H2S1 0.9600 . ?
C2S H2S2 0.9600 . ?
C2S H2S3 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.1(5) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 120.0(5) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 121.0(5) . . ?
C4 C3 Br1 119.1(4) . . ?
C2 C3 Br1 120.0(4) . . ?
C3 C4 C5 118.4(5) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 121.6(5) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C1 118.9(4) . . ?
C5 C6 C7 121.3(4) . . ?
C1 C6 C7 119.8(4) . . ?
C8 C7 C17 109.8(4) . . ?
C8 C7 C6 111.6(3) . . ?
C17 C7 C6 111.6(4) . . ?
C8 C7 H7 107.9 . . ?
C17 C7 H7 107.9 . . ?
C6 C7 H7 107.9 . . ?
C10 C8 C9 120.6(4) . . ?
C10 C8 C7 121.9(4) . . ?
C9 C8 C7 117.4(4) . . ?
N1 C9 C8 176.0(6) . . ?
C8 C10 N3 123.6(4) . . ?
C8 C10 N2 129.1(4) . . ?
N3 C10 N2 107.3(4) . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 C11' H11D 109.5 . . ?
C12 C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C12 C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
N3 C12 C13 101.4(5) . . ?
N3 C12 C11 117.3(6) . . ?
C13 C12 C11 111.6(5) . . ?
N3 C12 C11' 129.0(19) . . ?
C13 C12 C11' 124(2) . . ?
N3 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12A 108.7 . . ?
N3 C12 H12B 98.0 . . ?
C13 C12 H12B 98.0 . . ?
C11' C12 H12B 98.0 . . ?
O1 C13 N2 125.6(6) . . ?
O1 C13 C12 126.2(6) . . ?
N2 C13 C12 108.3(5) . . ?
C17 C14 N3 121.6(4) . . ?
C17 C14 C15 124.9(5) . . ?
N3 C14 C15 113.4(4) . . ?
O2 C15 O3 126.2(5) . . ?
O2 C15 C14 121.9(5) . . ?
O3 C15 C14 111.9(5) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 C18 123.4(4) . . ?
C14 C17 C7 123.0(4) . . ?
C18 C17 C7 113.6(4) . . ?
O4 C18 O5 123.7(5) . . ?
O4 C18 C17 123.0(5) . . ?
O5 C18 C17 113.3(5) . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 N2 C10 111.8(4) . . ?
C13 N2 H2A 124.1 . . ?
C10 N2 H2A 124.1 . . ?
C10 N3 C14 118.5(4) . . ?
C10 N3 C12 110.7(4) . . ?
C14 N3 C12 127.7(4) . . ?
C15 O3 C16 114.6(6) . . ?
C18 O5 C19 117.7(5) . . ?
C1S O1S H1S 109.5 . . ?
O1S C1S C2S 107.6(7) . . ?
O1S C1S H1S1 110.2 . . ?
C2S C1S H1S1 110.2 . . ?
O1S C1S H1S2 110.2 . . ?
C2S C1S H1S2 110.2 . . ?
H1S1 C1S H1S2 108.5 . . ?
C1S C2S H2S1 109.5 . . ?
C1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
C1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(9) . . . . ?
C1 C2 C3 C4 0.9(9) . . . . ?
C1 C2 C3 Br1 179.6(5) . . . . ?
C2 C3 C4 C5 -0.4(9) . . . . ?
Br1 C3 C4 C5 -179.2(4) . . . . ?
C3 C4 C5 C6 -0.6(8) . . . . ?
C4 C5 C6 C1 1.1(8) . . . . ?
C4 C5 C6 C7 180.0(5) . . . . ?
C2 C1 C6 C5 -0.6(8) . . . . ?
C2 C1 C6 C7 -179.5(5) . . . . ?
C5 C6 C7 C8 -56.5(6) . . . . ?
C1 C6 C7 C8 122.4(5) . . . . ?
C5 C6 C7 C17 66.7(6) . . . . ?
C1 C6 C7 C17 -114.4(5) . . . . ?
C17 C7 C8 C10 -8.5(6) . . . . ?
C6 C7 C8 C10 115.7(5) . . . . ?
C17 C7 C8 C9 173.7(4) . . . . ?
C6 C7 C8 C9 -62.1(6) . . . . ?
C9 C8 C10 N3 176.0(4) . . . . ?
C7 C8 C10 N3 -1.6(7) . . . . ?
C9 C8 C10 N2 -4.8(8) . . . . ?
C7 C8 C10 N2 177.5(4) . . . . ?
N3 C12 C13 O1 179.5(7) . . . . ?
C11 C12 C13 O1 53.9(10) . . . . ?
C11' C12 C13 O1 -26(2) . . . . ?
N3 C12 C13 N2 0.5(6) . . . . ?
C11 C12 C13 N2 -125.2(7) . . . . ?
C11' C12 C13 N2 155(2) . . . . ?
C17 C14 C15 O2 -93.1(7) . . . . ?
N3 C14 C15 O2 83.0(6) . . . . ?
C17 C14 C15 O3 90.2(6) . . . . ?
N3 C14 C15 O3 -93.7(5) . . . . ?
N3 C14 C17 C18 173.7(4) . . . . ?
C15 C14 C17 C18 -10.5(7) . . . . ?
N3 C14 C17 C7 -4.4(7) . . . . ?
C15 C14 C17 C7 171.4(4) . . . . ?
C8 C7 C17 C14 11.5(6) . . . . ?
C6 C7 C17 C14 -112.7(5) . . . . ?
C8 C7 C17 C18 -166.7(4) . . . . ?
C6 C7 C17 C18 69.1(5) . . . . ?
C14 C17 C18 O4 -161.5(5) . . . . ?
C7 C17 C18 O4 16.7(6) . . . . ?
C14 C17 C18 O5 17.2(6) . . . . ?
C7 C17 C18 O5 -164.6(4) . . . . ?
O1 C13 N2 C10 175.8(7) . . . . ?
C12 C13 N2 C10 -5.1(6) . . . . ?
C8 C10 N2 C13 -171.3(5) . . . . ?
N3 C10 N2 C13 7.9(6) . . . . ?
C8 C10 N3 C14 10.1(7) . . . . ?
N2 C10 N3 C14 -169.2(4) . . . . ?
C8 C10 N3 C12 171.8(5) . . . . ?
N2 C10 N3 C12 -7.5(5) . . . . ?
C17 C14 N3 C10 -7.0(6) . . . . ?
C15 C14 N3 C10 176.7(4) . . . . ?
C17 C14 N3 C12 -165.2(5) . . . . ?
C15 C14 N3 C12 18.6(7) . . . . ?
C13 C12 N3 C10 4.3(6) . . . . ?
C11 C12 N3 C10 126.1(6) . . . . ?
C13 C12 N3 C14 163.9(5) . . . . ?
C11 C12 N3 C14 -74.3(8) . . . . ?
C11' C12 N3 C14 11(3) . . . . ?
O2 C15 O3 C16 4.8(10) . . . . ?
C14 C15 O3 C16 -178.6(7) . . . . ?
O4 C18 O5 C19 1.0(7) . . . . ?
C17 C18 O5 C19 -177.7(4) . . . . ?

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 H2A O1S 0.86 1.90 2.759(7) 172.2 1_455
O1S H1S N1 0.82 2.14 2.896(8) 153.9 2_665

_refine_diff_density_max         0.847
_refine_diff_density_min         -1.053
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_1l
_database_code_depnum_ccdc_archive 'CCDC 1556664'
_audit_update_record             
;
2017-06-17 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H26 N4 O7'
_chemical_formula_sum            'C28 H26 N4 O7'
_chemical_formula_weight         530.53

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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

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

_cell_length_a                   26.9454(14)
_cell_length_b                   5.9941(3)
_cell_length_c                   20.0378(10)
_cell_angle_alpha                90
_cell_angle_beta                 121.9920(10)
_cell_angle_gamma                90
_cell_volume                     2744.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6830
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      21.23

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27452
_diffrn_reflns_av_unetI/netI     0.0840
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.533
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             6056
_reflns_number_gt                3473
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_max     0.909
_reflns_Friedel_fraction_full    0.937

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0946P)²+10.9827P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1025 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6056
_refine_ls_number_parameters     354
_refine_ls_number_restraints     73
_refine_ls_R_factor_all          0.2013
_refine_ls_R_factor_gt           0.1195
_refine_ls_wR_factor_ref         0.3179
_refine_ls_wR_factor_gt          0.2668
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.080
_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 0.1030(5) 0.483(2) 0.7172(8) 0.087(4) Uani 1 1 d . . . . .
H1 H 0.1249 0.5936 0.7119 0.104 Uiso 1 1 calc R U . . .
C2 C 0.0431(5) 0.507(3) 0.6777(9) 0.109(5) Uani 1 1 d . . . . .
H2 H 0.0246 0.6284 0.6449 0.131 Uiso 1 1 calc R U . . .
C3 C 0.0120(5) 0.348(3) 0.6878(9) 0.100(4) Uani 1 1 d . . . . .
C4 C 0.0380(6) 0.173(3) 0.7350(10) 0.114(5) Uani 1 1 d . . . . .
H4 H 0.0157 0.0681 0.7419 0.137 Uiso 1 1 calc R U . . .
C5 C 0.1000(5) 0.146(2) 0.7751(8) 0.097(4) Uani 1 1 d . . . . .
H5 H 0.1185 0.0245 0.8078 0.117 Uiso 1 1 calc R U . . .
C6 C 0.1313(4) 0.3044(16) 0.7639(5) 0.057(2) Uani 1 1 d . . . . .
C7 C 0.1979(4) 0.2795(17) 0.8045(5) 0.054(2) Uani 1 1 d . . . . .
H7 H 0.2098 0.1387 0.8338 0.064 Uiso 1 1 calc R U . . .
C8 C 0.2300(4) 0.4687(16) 0.8610(5) 0.049(2) Uani 1 1 d . . . . .
C9 C 0.2215(4) 0.4924(17) 0.9250(6) 0.059(2) Uani 1 1 d . . . . .
C10 C 0.2648(3) 0.6076(15) 0.8523(4) 0.0451(19) Uani 1 1 d . . . . .
C11 C 0.2133(4) 0.2721(16) 0.7415(5) 0.051(2) Uani 1 1 d . . . . .
C12 C 0.1841(4) 0.0915(19) 0.6838(6) 0.063(2) Uani 1 1 d . . . . .
C13 C 0.1387(5) -0.019(3) 0.5506(7) 0.104(4) Uani 1 1 d . . . . .
H13A H 0.1439 0.0114 0.5071 0.125 Uiso 1 1 calc R U . . .
H13B H 0.1546 -0.1660 0.5712 0.125 Uiso 1 1 calc R U . . .
C14 C 0.0771(8) -0.016(5) 0.5229(12) 0.190(10) Uani 1 1 d . . . . .
H14A H 0.0722 0.0215 0.5657 0.285 Uiso 1 1 calc R U . . .
H14B H 0.0604 -0.1599 0.5026 0.285 Uiso 1 1 calc R U . . .
H14C H 0.0577 0.0939 0.4820 0.285 Uiso 1 1 calc R U . . .
C15 C 0.2494(3) 0.4209(15) 0.7387(4) 0.0447(19) Uani 1 1 d . . . . .
C16 C 0.2634(4) 0.422(2) 0.6749(6) 0.062(2) Uani 1 1 d . . . . .
C17 C 0.3193(8) 0.235(3) 0.6288(10) 0.128(6) Uani 1 1 d . . . . .
H17A H 0.3183 0.3832 0.6084 0.154 Uiso 1 1 calc R U . . .
H17B H 0.3596 0.1846 0.6581 0.154 Uiso 1 1 calc R U . . .
C18 C 0.2861(9) 0.093(4) 0.5687(10) 0.158(8) Uani 1 1 d . . . . .
H18A H 0.2797 -0.0412 0.5891 0.238 Uiso 1 1 calc R U . . .
H18B H 0.3058 0.0583 0.5419 0.238 Uiso 1 1 calc R U . . .
H18C H 0.2491 0.1621 0.5326 0.238 Uiso 1 1 calc R U . . .
C19 C 0.3238(4) 0.902(2) 0.8667(5) 0.062(2) Uani 1 1 d . . . . .
C20 C 0.3149(4) 0.7666(18) 0.7967(5) 0.057(2) Uani 1 1 d . . . . .
H20 H 0.2926 0.8564 0.7488 0.068 Uiso 1 1 calc R U . . .
C21 C 0.3731(5) 0.701(2) 0.8066(6) 0.077(3) Uani 1 1 d . . . . .
H21A H 0.3655 0.6221 0.7598 0.093 Uiso 1 1 calc R U . . .
H21B H 0.3948 0.8351 0.8112 0.093 Uiso 1 1 calc R U . . .
C22 C 0.4088(6) 0.562(3) 0.8741(9) 0.111(5) Uani 1 1 d . . . . .
H22A H 0.3880 0.4241 0.8682 0.134 Uiso 1 1 calc R U . . .
H22B H 0.4148 0.6373 0.9206 0.134 Uiso 1 1 calc R U . . .
C23 C 0.4680(7) 0.507(3) 0.8859(12) 0.169(3) Uani 1 1 d D U . . .
C24 C 0.5129(6) 0.660(3) 0.9124(10) 0.169(3) Uani 1 1 d D U . . .
H24 H 0.5038 0.8044 0.9197 0.203 Uiso 1 1 calc R U . . .
C25 C 0.5695(6) 0.631(3) 0.9296(12) 0.169(3) Uani 1 1 d D U . . .
H25 H 0.5966 0.7457 0.9430 0.203 Uiso 1 1 calc R U . . .
C26 C 0.5801(8) 0.409(3) 0.9240(13) 0.170(3) Uani 1 1 d D U . . .
H26 H 0.6190 0.3664 0.9463 0.204 Uiso 1 1 calc R U . . .
C27 C 0.5384(6) 0.243(3) 0.8885(12) 0.171(3) Uani 1 1 d D U . . .
H27 H 0.5463 0.1064 0.8742 0.205 Uiso 1 1 calc R U . . .
C28 C 0.4836(7) 0.296(3) 0.8755(12) 0.170(3) Uani 1 1 d D U . . .
H28 H 0.4559 0.1822 0.8589 0.204 Uiso 1 1 calc R U . . .
N1 N -0.0512(7) 0.366(5) 0.6493(13) 0.208(5) Uani 1 1 d . U . . .
N2 N 0.2134(4) 0.5012(18) 0.9755(5) 0.088(3) Uani 1 1 d . . . . .
N3 N 0.2776(3) 0.5862(13) 0.7948(4) 0.0491(17) Uani 1 1 d . . . . .
N4 N 0.2943(3) 0.7944(14) 0.8953(4) 0.0538(18) Uani 1 1 d . . . . .
H4A H 0.2942 0.8384 0.9360 0.065 Uiso 1 1 calc R U . . .
O1 O -0.0743(5) 0.520(4) 0.6022(10) 0.212(5) Uani 1 1 d . U . . .
O2 O -0.0789(5) 0.235(4) 0.6584(9) 0.208(5) Uani 1 1 d . U . . .
O3 O 0.3516(3) 1.0711(15) 0.8915(4) 0.083(2) Uani 1 1 d . . . . .
O4 O 0.1740(4) -0.0856(13) 0.7015(5) 0.084(2) Uani 1 1 d . . . . .
O5 O 0.1697(3) 0.1477(13) 0.6120(4) 0.079(2) Uani 1 1 d . . . . .
O6 O 0.2511(3) 0.5693(14) 0.6293(4) 0.076(2) Uani 1 1 d . . . . .
O7 O 0.2953(3) 0.2432(13) 0.6822(4) 0.078(2) 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 C6 1.359(14) . ?
C1 C2 1.376(15) . ?
C1 H1 0.9300 . ?
C2 C3 1.354(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.334(19) . ?
C3 N1 1.45(2) . ?
C4 C5 1.428(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.365(14) . ?
C5 H5 0.9300 . ?
C6 C7 1.534(12) . ?
C7 C8 1.509(13) . ?
C7 C11 1.526(11) . ?
C7 H7 0.9800 . ?
C8 C10 1.334(11) . ?
C8 C9 1.424(11) . ?
C9 N2 1.143(11) . ?
C10 N3 1.372(9) . ?
C10 N4 1.379(11) . ?
C11 C15 1.342(11) . ?
C11 C12 1.471(14) . ?
C12 O4 1.195(12) . ?
C12 O5 1.321(11) . ?
C13 C14 1.44(2) . ?
C13 O5 1.458(13) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N3 1.385(10) . ?
C15 C16 1.512(11) . ?
C16 O6 1.184(11) . ?
C16 O7 1.334(12) . ?
C17 C18 1.35(2) . ?
C17 O7 1.515(14) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O3 1.200(12) . ?
C19 N4 1.362(12) . ?
C19 C20 1.527(13) . ?
C20 N3 1.464(11) . ?
C20 C21 1.525(13) . ?
C20 H20 0.9800 . ?
C21 C22 1.437(16) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.52(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.384(7) . ?
C23 C28 1.384(7) . ?
C24 C25 1.385(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.381(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.382(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.392(7) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
N1 O2 1.16(2) . ?
N1 O1 1.23(2) . ?
N4 H4A 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.5(12) . . ?
C6 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 118.1(13) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C4 C3 C2 121.6(12) . . ?
C4 C3 N1 117.6(16) . . ?
C2 C3 N1 120.7(16) . . ?
C3 C4 C5 120.4(12) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.0(12) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C1 C6 C5 119.3(10) . . ?
C1 C6 C7 121.0(8) . . ?
C5 C6 C7 119.7(9) . . ?
C8 C7 C11 110.1(7) . . ?
C8 C7 C6 111.7(7) . . ?
C11 C7 C6 108.6(7) . . ?
C8 C7 H7 108.8 . . ?
C11 C7 H7 108.8 . . ?
C6 C7 H7 108.8 . . ?
C10 C8 C9 121.0(8) . . ?
C10 C8 C7 122.3(7) . . ?
C9 C8 C7 116.6(8) . . ?
N2 C9 C8 176.6(11) . . ?
C8 C10 N3 124.0(8) . . ?
C8 C10 N4 129.6(7) . . ?
N3 C10 N4 106.4(7) . . ?
C15 C11 C12 123.7(8) . . ?
C15 C11 C7 122.5(8) . . ?
C12 C11 C7 113.8(7) . . ?
O4 C12 O5 124.6(10) . . ?
O4 C12 C11 122.2(9) . . ?
O5 C12 C11 113.2(9) . . ?
C14 C13 O5 110.0(12) . . ?
C14 C13 H13A 109.7 . . ?
O5 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
O5 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 N3 122.6(7) . . ?
C11 C15 C16 123.3(8) . . ?
N3 C15 C16 114.1(7) . . ?
O6 C16 O7 125.7(8) . . ?
O6 C16 C15 124.3(9) . . ?
O7 C16 C15 109.8(8) . . ?
C18 C17 O7 108.5(15) . . ?
C18 C17 H17A 110.0 . . ?
O7 C17 H17A 110.0 . . ?
C18 C17 H17B 110.0 . . ?
O7 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 N4 126.9(9) . . ?
O3 C19 C20 126.0(9) . . ?
N4 C19 C20 107.0(9) . . ?
N3 C20 C21 117.2(9) . . ?
N3 C20 C19 100.8(7) . . ?
C21 C20 C19 111.6(8) . . ?
N3 C20 H20 108.9 . . ?
C21 C20 H20 108.9 . . ?
C19 C20 H20 108.9 . . ?
C22 C21 C20 113.7(9) . . ?
C22 C21 H21A 108.8 . . ?
C20 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
C20 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 C23 113.4(11) . . ?
C21 C22 H22A 108.9 . . ?
C23 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
C23 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C24 C23 C28 113.1(18) . . ?
C24 C23 C22 123.2(15) . . ?
C28 C23 C22 123.6(15) . . ?
C23 C24 C25 129.5(19) . . ?
C23 C24 H24 115.2 . . ?
C25 C24 H24 115.2 . . ?
C26 C25 C24 110.4(18) . . ?
C26 C25 H25 124.8 . . ?
C24 C25 H25 124.8 . . ?
C25 C26 C27 126.1(19) . . ?
C25 C26 H26 116.9 . . ?
C27 C26 H26 116.9 . . ?
C26 C27 C28 115.3(18) . . ?
C26 C27 H27 122.4 . . ?
C28 C27 H27 122.4 . . ?
C23 C28 C27 123.7(19) . . ?
C23 C28 H28 118.2 . . ?
C27 C28 H28 118.2 . . ?
O2 N1 O1 121.3(19) . . ?
O2 N1 C3 122(2) . . ?
O1 N1 C3 116.2(19) . . ?
C10 N3 C15 118.4(7) . . ?
C10 N3 C20 112.6(7) . . ?
C15 N3 C20 128.5(6) . . ?
C19 N4 C10 113.2(7) . . ?
C19 N4 H4A 123.4 . . ?
C10 N4 H4A 123.4 . . ?
C12 O5 C13 116.8(9) . . ?
C16 O7 C17 116.1(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 2(2) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C1 C2 C3 N1 178.4(16) . . . . ?
C2 C3 C4 C5 -2(3) . . . . ?
N1 C3 C4 C5 -179.5(16) . . . . ?
C3 C4 C5 C6 0(2) . . . . ?
C2 C1 C6 C5 -2.9(19) . . . . ?
C2 C1 C6 C7 177.6(12) . . . . ?
C4 C5 C6 C1 1.8(18) . . . . ?
C4 C5 C6 C7 -178.8(11) . . . . ?
C1 C6 C7 C8 61.8(12) . . . . ?
C5 C6 C7 C8 -117.6(10) . . . . ?
C1 C6 C7 C11 -59.8(12) . . . . ?
C5 C6 C7 C11 120.8(10) . . . . ?
C11 C7 C8 C10 1.9(11) . . . . ?
C6 C7 C8 C10 -118.8(9) . . . . ?
C11 C7 C8 C9 -177.9(7) . . . . ?
C6 C7 C8 C9 61.4(10) . . . . ?
C9 C8 C10 N3 176.1(8) . . . . ?
C7 C8 C10 N3 -3.8(12) . . . . ?
C9 C8 C10 N4 -4.4(13) . . . . ?
C7 C8 C10 N4 175.8(8) . . . . ?
C8 C7 C11 C15 -1.6(11) . . . . ?
C6 C7 C11 C15 120.9(9) . . . . ?
C8 C7 C11 C12 179.8(7) . . . . ?
C6 C7 C11 C12 -57.7(10) . . . . ?
C15 C11 C12 O4 147.1(9) . . . . ?
C7 C11 C12 O4 -34.4(13) . . . . ?
C15 C11 C12 O5 -34.1(12) . . . . ?
C7 C11 C12 O5 144.5(8) . . . . ?
C12 C11 C15 N3 -178.4(8) . . . . ?
C7 C11 C15 N3 3.1(12) . . . . ?
C12 C11 C15 C16 1.0(13) . . . . ?
C7 C11 C15 C16 -177.4(8) . . . . ?
C11 C15 C16 O6 116.3(12) . . . . ?
N3 C15 C16 O6 -64.2(12) . . . . ?
C11 C15 C16 O7 -68.8(11) . . . . ?
N3 C15 C16 O7 110.7(9) . . . . ?
O3 C19 C20 N3 -179.4(10) . . . . ?
N4 C19 C20 N3 0.8(9) . . . . ?
O3 C19 C20 C21 55.5(14) . . . . ?
N4 C19 C20 C21 -124.4(9) . . . . ?
N3 C20 C21 C22 -54.0(14) . . . . ?
C19 C20 C21 C22 61.5(14) . . . . ?
C20 C21 C22 C23 -177.1(13) . . . . ?
C21 C22 C23 C24 73(2) . . . . ?
C21 C22 C23 C28 -111(2) . . . . ?
C28 C23 C24 C25 0(2) . . . . ?
C22 C23 C24 C25 176.4(18) . . . . ?
C23 C24 C25 C26 -6(2) . . . . ?
C24 C25 C26 C27 15(3) . . . . ?
C25 C26 C27 C28 -17(3) . . . . ?
C24 C23 C28 C27 -1(3) . . . . ?
C22 C23 C28 C27 -178.2(18) . . . . ?
C26 C27 C28 C23 9(3) . . . . ?
C4 C3 N1 O2 0(3) . . . . ?
C2 C3 N1 O2 -178(2) . . . . ?
C4 C3 N1 O1 -175(2) . . . . ?
C2 C3 N1 O1 7(3) . . . . ?
C8 C10 N3 C15 4.9(11) . . . . ?
N4 C10 N3 C15 -174.7(7) . . . . ?
C8 C10 N3 C20 177.6(8) . . . . ?
N4 C10 N3 C20 -2.1(9) . . . . ?
C11 C15 N3 C10 -4.6(11) . . . . ?
C16 C15 N3 C10 175.9(7) . . . . ?
C11 C15 N3 C20 -175.9(8) . . . . ?
C16 C15 N3 C20 4.6(12) . . . . ?
C21 C20 N3 C10 122.1(8) . . . . ?
C19 C20 N3 C10 0.8(9) . . . . ?
C21 C20 N3 C15 -66.2(11) . . . . ?
C19 C20 N3 C15 172.5(8) . . . . ?
O3 C19 N4 C10 178.0(10) . . . . ?
C20 C19 N4 C10 -2.2(10) . . . . ?
C8 C10 N4 C19 -177.0(9) . . . . ?
N3 C10 N4 C19 2.7(9) . . . . ?
O4 C12 O5 C13 0.9(15) . . . . ?
C11 C12 O5 C13 -178.0(9) . . . . ?
C14 C13 O5 C12 81.8(17) . . . . ?
O6 C16 O7 C17 2.4(17) . . . . ?
C15 C16 O7 C17 -172.5(10) . . . . ?
C18 C17 O7 C16 -102.5(16) . . . . ?

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
N4 H4A N2 0.86 2.13 2.976(11) 169.5 4_557

_refine_diff_density_max         0.523
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.061

