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

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

data_zmd25dhba
_database_code_depnum_ccdc_archive 'CCDC 1522933'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2017-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N O6'
_chemical_formula_weight         319.31

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

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

_cell_length_a                   8.0456(3)
_cell_length_b                   9.1098(4)
_cell_length_c                   22.6193(9)
_cell_angle_alpha                94.2433(16)
_cell_angle_beta                 91.5013(17)
_cell_angle_gamma                113.8431(16)
_cell_volume                     1509.35(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9912
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      32.65

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9589
_exptl_absorpt_correction_T_max  0.9765
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            41291
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         32.75
_reflns_number_total             11027
_reflns_number_gt                8850
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0498P)²+0.6737P] 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         11027
_refine_ls_number_parameters     457
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1383
_refine_ls_wR_factor_gt          0.1310
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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 0.10584(16) 0.87903(15) -0.09845(5) 0.0207(2) Uani 1 1 d . . .
O1 O 0.02320(13) 0.88578(13) -0.14460(4) 0.0272(2) Uani 1 1 d . . .
N1 N 0.14045(18) 0.75079(14) -0.08886(6) 0.0273(2) Uani 1 1 d . . .
C2 C 0.17482(16) 1.02123(14) -0.05267(5) 0.0182(2) Uani 1 1 d . . .
C7 C 0.15770(17) 1.15983(15) -0.06900(5) 0.0217(2) Uani 1 1 d . . .
H7 H 0.1058 1.1579 -0.1064 0.026 Uiso 1 1 calc R . .
C3 C 0.25253(16) 1.02571(14) 0.00434(5) 0.0185(2) Uani 1 1 d . . .
C4 C 0.30766(18) 1.16574(15) 0.04300(6) 0.0225(2) Uani 1 1 d . . .
H4 H 0.3563 1.1680 0.0810 0.027 Uiso 1 1 calc R . .
C5 C 0.29036(19) 1.30177(15) 0.02515(6) 0.0257(3) Uani 1 1 d . . .
H5 H 0.3291 1.3949 0.0511 0.031 Uiso 1 1 calc R . .
C6 C 0.21592(19) 1.30005(16) -0.03093(6) 0.0257(2) Uani 1 1 d . . .
H6 H 0.2051 1.3915 -0.0429 0.031 Uiso 1 1 calc R . .
O2 O 0.27068(13) 0.89083(11) 0.01999(4) 0.02363(18) Uani 1 1 d . . .
C8 C 0.33030(19) 0.88736(17) 0.08036(6) 0.0261(2) Uani 1 1 d . . .
H12A H 0.2499 0.9079 0.1078 0.031 Uiso 1 1 calc R . .
H8B H 0.4528 0.9690 0.0895 0.031 Uiso 1 1 calc R . .
C9 C 0.3259(2) 0.7221(2) 0.08543(8) 0.0376(3) Uani 1 1 d . . .
H11A H 0.2045 0.6424 0.0756 0.056 Uiso 1 1 calc R . .
H9B H 0.3628 0.7143 0.1254 0.056 Uiso 1 1 calc R . .
H9C H 0.4075 0.7041 0.0585 0.056 Uiso 1 1 calc R . .
O5 O 1.09006(12) 0.83389(12) 0.21653(5) 0.0278(2) Uani 1 1 d . . .
O6 O 0.95314(12) 0.95199(11) 0.27583(4) 0.02351(19) Uani 1 1 d . . .
C10 C 0.76977(15) 0.70464(13) 0.22077(5) 0.01661(19) Uani 1 1 d . . .
C15 C 0.61095(16) 0.70827(14) 0.24329(5) 0.0185(2) Uani 1 1 d . . .
H15 H 0.6185 0.7951 0.2693 0.022 Uiso 1 1 calc R . .
C11 C 0.75813(15) 0.57275(13) 0.18186(5) 0.0171(2) Uani 1 1 d . . .
C13 C 0.43201(16) 0.45341(14) 0.18826(5) 0.0192(2) Uani 1 1 d . . .
H13 H 0.3196 0.3697 0.1772 0.023 Uiso 1 1 calc R . .
C14 C 0.44232(16) 0.58384(14) 0.22730(5) 0.0190(2) Uani 1 1 d . . .
C12 C 0.58848(16) 0.44869(14) 0.16608(5) 0.0192(2) Uani 1 1 d . . .
H12 H 0.5802 0.3614 0.1403 0.023 Uiso 1 1 calc R . .
O8 O 0.70208(11) 0.20255(11) 0.44047(4) 0.02198(18) Uani 1 1 d . . .
O7 O 0.27528(12) 0.22150(11) 0.53427(4) 0.02371(19) Uani 1 1 d . . .
N2 N 0.57193(15) 0.35329(13) 0.51766(5) 0.0238(2) Uani 1 1 d . . .
C16 C 0.85471(17) 0.18082(16) 0.41560(6) 0.0235(2) Uani 1 1 d . . .
H16A H 0.8428 0.1721 0.3726 0.028 Uiso 1 1 calc R . .
H16B H 0.8618 0.0837 0.4280 0.028 Uiso 1 1 calc R . .
C17 C 1.02238(18) 0.32765(19) 0.43866(7) 0.0313(3) Uani 1 1 d . . .
H17A H 1.0136 0.4226 0.4259 0.047 Uiso 1 1 calc R . .
H17B H 1.1285 0.3186 0.4235 0.047 Uiso 1 1 calc R . .
H17C H 1.0316 0.3351 0.4813 0.047 Uiso 1 1 calc R . .
C19 C 0.38674(15) 0.10342(14) 0.45701(5) 0.0172(2) Uani 1 1 d . . .
C18 C 0.53031(15) 0.08732(14) 0.42665(5) 0.0179(2) Uani 1 1 d . . .
C20 C 0.20956(16) -0.01079(15) 0.44212(5) 0.0206(2) Uani 1 1 d . . .
H20 H 0.1136 -0.0015 0.4617 0.025 Uiso 1 1 calc R . .
C22 C 0.31632(19) -0.15333(16) 0.37033(6) 0.0264(3) Uani 1 1 d . . .
H22 H 0.2929 -0.2389 0.3416 0.032 Uiso 1 1 calc R . .
C21 C 0.17326(18) -0.13747(16) 0.39891(6) 0.0253(2) Uani 1 1 d . . .
H21 H 0.0541 -0.2112 0.3892 0.030 Uiso 1 1 calc R . .
O12 O 0.99509(11) 0.30326(11) 0.24109(4) 0.02160(18) Uani 1 1 d . . .
O9 O 0.29572(11) 0.19094(11) 0.30325(4) 0.02344(19) Uani 1 1 d . . .
O10 O 0.43877(12) 0.44642(12) 0.37567(4) 0.02501(19) Uani 1 1 d . . .
O11 O 0.74100(12) 0.58289(11) 0.38463(4) 0.0253(2) Uani 1 1 d . . .
C24 C 0.62030(15) 0.35532(13) 0.31497(5) 0.01613(19) Uani 1 1 d . . .
C29 C 0.79561(15) 0.38223(13) 0.29760(5) 0.0171(2) Uani 1 1 d . . .
H29 H 0.8952 0.4731 0.3138 0.020 Uiso 1 1 calc R . .
C26 C 0.49657(16) 0.11053(14) 0.24839(5) 0.0199(2) Uani 1 1 d . . .
H26 H 0.3974 0.0199 0.2318 0.024 Uiso 1 1 calc R . .
C27 C 0.67068(16) 0.13675(14) 0.23241(5) 0.0185(2) Uani 1 1 d . . .
H27 H 0.6880 0.0626 0.2055 0.022 Uiso 1 1 calc R . .
C28 C 0.82109(15) 0.27414(13) 0.25643(5) 0.0169(2) Uani 1 1 d . . .
C25 C 0.47010(15) 0.22005(14) 0.28933(5) 0.0174(2) Uani 1 1 d . . .
C30 C 0.59311(15) 0.46603(14) 0.36084(5) 0.0182(2) Uani 1 1 d . . .
C31 C 0.49427(17) -0.04244(15) 0.38427(6) 0.0224(2) Uani 1 1 d . . .
H31 H 0.5895 -0.0549 0.3653 0.027 Uiso 1 1 calc R . .
O19 O 0.90725(12) 0.56001(11) 0.15856(4) 0.02315(18) Uani 1 1 d . . .
O20 O 0.29132(13) 0.59496(12) 0.24936(5) 0.0288(2) Uani 1 1 d . . .
C32 C 0.95063(16) 0.83428(14) 0.23731(5) 0.0191(2) Uani 1 1 d . . .
H1A H 1.006(4) 0.651(3) 0.1774(11) 0.065(7) Uiso 1 1 d . . .
H4A H 0.193(3) 0.748(3) -0.0552(10) 0.041(5) Uiso 1 1 d . . .
H5A H 0.100(3) 0.665(3) -0.1146(9) 0.039(5) Uiso 1 1 d . . .
H2A H 0.711(4) 0.657(4) 0.4175(13) 0.082(9) Uiso 1 1 d . . .
H3A H 0.667(3) 0.355(2) 0.4981(9) 0.037(5) Uiso 1 1 d . . .
H6A H 0.587(3) 0.425(3) 0.5501(9) 0.041(5) Uiso 1 1 d . . .
H8A H 1.079(3) 1.025(3) 0.2839(11) 0.061(7) Uiso 1 1 d . . .
H9A H 0.992(3) 0.232(3) 0.2097(10) 0.050(6) Uiso 1 1 d . . .
H10A H 0.306(4) 0.273(3) 0.3332(12) 0.070(8) Uiso 1 1 d . . .
C33 C 0.41049(16) 0.23154(14) 0.50557(5) 0.0181(2) Uani 1 1 d . . .
H20A H 0.198(3) 0.501(3) 0.2462(10) 0.052(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2416(16) . ?
C1 N1 1.3367(18) . ?
C1 C2 1.4996(16) . ?
N1 H4A 0.87(2) . ?
N1 H5A 0.88(2) . ?
C2 C7 1.3988(17) . ?
C2 C3 1.4088(17) . ?
C7 C6 1.3874(17) . ?
C7 H7 0.9300 . ?
C3 O2 1.3649(15) . ?
C3 C4 1.3949(16) . ?
C4 C5 1.3888(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.3850(19) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
O2 C8 1.4422(16) . ?
C8 C9 1.504(2) . ?
C8 H12A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H11A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
O5 C32 1.2288(15) . ?
O6 C32 1.3239(14) . ?
O6 H8A 0.96(3) . ?
C10 C15 1.3997(16) . ?
C10 C11 1.4053(15) . ?
C10 C32 1.4727(16) . ?
C15 C14 1.3880(16) . ?
C15 H15 0.9300 . ?
C11 O19 1.3665(14) . ?
C11 C12 1.3912(16) . ?
C13 C12 1.3828(16) . ?
C13 C14 1.3998(15) . ?
C13 H13 0.9300 . ?
C14 O20 1.3634(14) . ?
C12 H12 0.9300 . ?
O8 C18 1.3658(14) . ?
O8 C16 1.4422(15) . ?
O7 C33 1.2564(14) . ?
N2 C33 1.3281(15) . ?
N2 H3A 0.89(2) . ?
N2 H6A 0.92(2) . ?
C16 C17 1.5107(19) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 C20 1.3971(16) . ?
C19 C18 1.4110(16) . ?
C19 C33 1.4913(15) . ?
C18 C31 1.3932(16) . ?
C20 C21 1.3849(17) . ?
C20 H20 0.9300 . ?
C22 C21 1.3868(19) . ?
C22 C31 1.3891(18) . ?
C22 H22 0.9300 . ?
C21 H21 0.9300 . ?
O12 C28 1.3746(13) . ?
O12 H9A 0.92(2) . ?
O9 C25 1.3684(14) . ?
O9 H10A 0.95(3) . ?
O10 C30 1.2401(14) . ?
O11 C30 1.3024(14) . ?
O11 H2A 1.06(3) . ?
C24 C29 1.4027(15) . ?
C24 C25 1.4032(15) . ?
C24 C30 1.4754(15) . ?
C29 C28 1.3843(15) . ?
C29 H29 0.9300 . ?
C26 C27 1.3852(16) . ?
C26 C25 1.3941(15) . ?
C26 H26 0.9300 . ?
C27 C28 1.4023(15) . ?
C27 H27 0.9300 . ?
C31 H31 0.9300 . ?
O19 H1A 0.95(3) . ?
O20 H20A 0.88(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 122.19(11) . . ?
O1 C1 C2 119.16(12) . . ?
N1 C1 C2 118.62(12) . . ?
C1 N1 H4A 119.6(14) . . ?
C1 N1 H5A 120.3(14) . . ?
H4A N1 H5A 120(2) . . ?
C7 C2 C3 118.37(10) . . ?
C7 C2 C1 115.81(11) . . ?
C3 C2 C1 125.81(11) . . ?
C6 C7 C2 121.86(12) . . ?
C6 C7 H7 119.1 . . ?
C2 C7 H7 119.1 . . ?
O2 C3 C4 122.02(11) . . ?
O2 C3 C2 118.29(10) . . ?
C4 C3 C2 119.70(11) . . ?
C5 C4 C3 120.44(12) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 120.64(11) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 118.97(12) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C3 O2 C8 118.78(10) . . ?
O2 C8 C9 106.90(12) . . ?
O2 C8 H12A 110.3 . . ?
C9 C8 H12A 110.3 . . ?
O2 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H12A C8 H8B 108.6 . . ?
C8 C9 H11A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H11A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H11A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C32 O6 H8A 106.9(15) . . ?
C15 C10 C11 119.49(10) . . ?
C15 C10 C32 121.97(10) . . ?
C11 C10 C32 118.53(10) . . ?
C14 C15 C10 120.78(10) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
O19 C11 C12 117.88(10) . . ?
O19 C11 C10 122.83(10) . . ?
C12 C11 C10 119.29(10) . . ?
C12 C13 C14 120.21(10) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
O20 C14 C15 118.49(10) . . ?
O20 C14 C13 122.19(10) . . ?
C15 C14 C13 119.30(10) . . ?
C13 C12 C11 120.92(10) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C18 O8 C16 119.22(9) . . ?
C33 N2 H3A 119.6(13) . . ?
C33 N2 H6A 118.6(13) . . ?
H3A N2 H6A 120.9(19) . . ?
O8 C16 C17 106.22(11) . . ?
O8 C16 H16A 110.5 . . ?
C17 C16 H16A 110.5 . . ?
O8 C16 H16B 110.5 . . ?
C17 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C20 C19 C18 118.26(10) . . ?
C20 C19 C33 117.04(10) . . ?
C18 C19 C33 124.67(10) . . ?
O8 C18 C31 122.37(11) . . ?
O8 C18 C19 117.56(10) . . ?
C31 C18 C19 120.06(11) . . ?
C21 C20 C19 121.65(11) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C21 C22 C31 120.51(11) . . ?
C21 C22 H22 119.7 . . ?
C31 C22 H22 119.7 . . ?
C20 C21 C22 119.34(11) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C28 O12 H9A 109.9(14) . . ?
C25 O9 H10A 105.7(16) . . ?
C30 O11 H2A 111.5(16) . . ?
C29 C24 C25 119.62(10) . . ?
C29 C24 C30 120.56(10) . . ?
C25 C24 C30 119.81(10) . . ?
C28 C29 C24 120.29(10) . . ?
C28 C29 H29 119.9 . . ?
C24 C29 H29 119.9 . . ?
C27 C26 C25 119.98(10) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C28 120.55(10) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
O12 C28 C29 118.68(10) . . ?
O12 C28 C27 121.67(10) . . ?
C29 C28 C27 119.64(10) . . ?
O9 C25 C26 118.14(10) . . ?
O9 C25 C24 121.98(10) . . ?
C26 C25 C24 119.88(10) . . ?
O10 C30 O11 122.98(10) . . ?
O10 C30 C24 121.44(10) . . ?
O11 C30 C24 115.58(10) . . ?
C22 C31 C18 120.13(11) . . ?
C22 C31 H31 119.9 . . ?
C18 C31 H31 119.9 . . ?
C11 O19 H1A 103.2(15) . . ?
C14 O20 H20A 111.4(15) . . ?
O5 C32 O6 122.11(11) . . ?
O5 C32 C10 122.30(10) . . ?
O6 C32 C10 115.59(10) . . ?
O7 C33 N2 121.30(11) . . ?
O7 C33 C19 118.64(10) . . ?
N2 C33 C19 120.06(10) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        32.76
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_zmd34dhba
_database_code_depnum_ccdc_archive 'CCDC 1522937'
_audit_update_record             
;
2017-10-04 deposited with the CCDC.
2017-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 N O6'
_chemical_formula_weight         318.30

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   P2(1)/n

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

_cell_length_a                   15.720(5)
_cell_length_b                   4.0408(12)
_cell_length_c                   23.577(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.55(2)
_cell_angle_gamma                90.00
_cell_volume                     1496.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2445
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      31.10

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             668
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9711
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17630
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_av_sigmaI/netI    0.1281
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         31.87
_reflns_number_total             4810
_reflns_number_gt                1761
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.1065P)²+0.0000P] 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         4810
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1648
_refine_ls_R_factor_gt           0.0859
_refine_ls_wR_factor_ref         0.2317
_refine_ls_wR_factor_gt          0.1946
_refine_ls_goodness_of_fit_ref   0.851
_refine_ls_restrained_S_all      0.851
_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
C15 C 0.63011(18) -0.0347(8) 0.33638(11) 0.0428(7) Uani 1 1 d . . .
H15A H 0.5963 -0.1878 0.3577 0.051 Uiso 1 1 calc R . .
H15B H 0.6362 0.1699 0.3577 0.051 Uiso 1 1 calc R . .
O6 O 0.58985(11) 0.0271(5) 0.28105(7) 0.0421(5) Uani 1 1 d . . .
C12 C 0.39394(18) 0.4507(7) 0.31876(13) 0.0436(7) Uani 1 1 d . . .
H12 H 0.3681 0.5287 0.3509 0.052 Uiso 1 1 calc R . .
O2 O 0.08744(10) 0.0605(5) -0.03813(7) 0.0398(5) Uani 1 1 d . . .
O4 O 0.43666(10) 0.7602(5) 0.03260(7) 0.0420(5) Uani 1 1 d . . .
O3 O 0.38887(12) 0.4378(6) -0.06273(8) 0.0537(7) Uani 1 1 d . . .
C16 C 0.71505(18) -0.1793(9) 0.32634(12) 0.0546(9) Uani 1 1 d . . .
H16A H 0.7460 -0.0332 0.3026 0.082 Uiso 1 1 calc R . .
H16B H 0.7079 -0.3900 0.3079 0.082 Uiso 1 1 calc R . .
H16C H 0.7461 -0.2081 0.3620 0.082 Uiso 1 1 calc R . .
N2 N 0.57700(15) -0.0784(7) 0.16965(11) 0.0460(7) Uani 1 1 d . . .
C13 C 0.35361(17) 0.4946(8) 0.26627(14) 0.0462(8) Uani 1 1 d . . .
H13 H 0.3018 0.6051 0.2626 0.055 Uiso 1 1 calc R . .
C11 C 0.47088(18) 0.2955(8) 0.32483(12) 0.0423(7) Uani 1 1 d . . .
H11 H 0.4966 0.2688 0.3608 0.051 Uiso 1 1 calc R . .
C14 C 0.39235(17) 0.3694(8) 0.21869(12) 0.0427(7) Uani 1 1 d . . .
H14 H 0.3649 0.3916 0.1831 0.051 Uiso 1 1 calc R . .
O5 O 0.46291(12) 0.1319(6) 0.12327(8) 0.0520(6) Uani 1 1 d . . .
C6 C 0.29877(15) 0.6744(7) 0.07109(10) 0.0344(6) Uani 1 1 d . . .
H6 H 0.3136 0.7917 0.1040 0.041 Uiso 1 1 calc R . .
C5 C 0.35672(15) 0.6374(7) 0.02941(10) 0.0320(6) Uani 1 1 d . . .
C10 C 0.51123(15) 0.1765(8) 0.27736(11) 0.0364(7) Uani 1 1 d . . .
C9 C 0.47069(15) 0.2130(7) 0.22311(11) 0.0340(6) Uani 1 1 d . . .
C8 C 0.50427(16) 0.0828(7) 0.16848(11) 0.0357(7) Uani 1 1 d . . .
C1 C 0.10917(15) 0.2140(7) 0.00642(10) 0.0320(6) Uani 1 1 d . . .
C2 C 0.19459(14) 0.3637(7) 0.01433(10) 0.0296(6) Uani 1 1 d . . .
C7 C 0.21798(16) 0.5357(7) 0.06375(10) 0.0328(6) Uani 1 1 d . . .
H7 H 0.1792 0.5581 0.0922 0.039 Uiso 1 1 calc R . .
C3 C 0.25293(14) 0.3305(7) -0.02797(10) 0.0320(6) Uani 1 1 d . . .
H3 H 0.2377 0.2176 -0.0613 0.038 Uiso 1 1 calc R . .
C4 C 0.33330(15) 0.4651(7) -0.02056(10) 0.0333(6) Uani 1 1 d . . .
O1 O 0.05882(12) 0.2470(6) 0.04822(8) 0.0441(6) Uani 1 1 d . . .
H1A H 0.0159(19) 0.142(8) 0.0441(12) 0.049(10) Uiso 1 1 d . . .
H2B H 0.5992(16) -0.182(7) 0.1397(12) 0.044(8) Uiso 1 1 d . . .
H2A H 0.607(2) -0.132(9) 0.2031(14) 0.067(10) Uiso 1 1 d . . .
H3A H 0.461(4) 0.437(16) -0.060(3) 0.20(2) 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
C15 O6 1.446(3) . ?
C15 C16 1.486(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O6 C10 1.375(3) . ?
C12 C11 1.364(4) . ?
C12 C13 1.377(4) . ?
C12 H12 0.9300 . ?
O2 C1 1.254(3) . ?
O4 C5 1.350(3) . ?
O3 C4 1.357(3) . ?
O3 H3A 1.13(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N2 C8 1.315(3) . ?
N2 H2B 0.90(3) . ?
N2 H2A 0.93(3) . ?
C13 C14 1.395(4) . ?
C13 H13 0.9300 . ?
C11 C10 1.396(4) . ?
C11 H11 0.9300 . ?
C14 C9 1.384(4) . ?
C14 H14 0.9300 . ?
O5 C8 1.240(3) . ?
C6 C5 1.378(3) . ?
C6 C7 1.392(3) . ?
C6 H6 0.9300 . ?
C5 C4 1.403(3) . ?
C10 C9 1.411(3) . ?
C9 C8 1.508(4) . ?
C1 O1 1.298(3) . ?
C1 C2 1.477(3) . ?
C2 C3 1.391(3) . ?
C2 C7 1.392(3) . ?
C7 H7 0.9300 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
O1 H1A 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
O6 C15 C16 106.5(2) . . ?
O6 C15 H15A 110.4 . . ?
C16 C15 H15A 110.4 . . ?
O6 C15 H15B 110.4 . . ?
C16 C15 H15B 110.4 . . ?
H15A C15 H15B 108.6 . . ?
C10 O6 C15 119.3(2) . . ?
C11 C12 C13 121.6(3) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C4 O3 H3A 129(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 N2 H2B 125.3(17) . . ?
C8 N2 H2A 123(2) . . ?
H2B N2 H2A 111(3) . . ?
C12 C13 C14 118.4(3) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C9 C14 C13 121.6(3) . . ?
C9 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C5 C6 C7 119.7(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
O4 C5 C6 124.3(2) . . ?
O4 C5 C4 116.0(2) . . ?
C6 C5 C4 119.7(2) . . ?
O6 C10 C11 122.7(2) . . ?
O6 C10 C9 118.1(2) . . ?
C11 C10 C9 119.2(2) . . ?
C14 C9 C10 118.7(2) . . ?
C14 C9 C8 116.0(2) . . ?
C10 C9 C8 125.2(2) . . ?
O5 C8 N2 121.3(3) . . ?
O5 C8 C9 119.2(2) . . ?
N2 C8 C9 119.5(2) . . ?
O2 C1 O1 122.3(2) . . ?
O2 C1 C2 121.4(2) . . ?
O1 C1 C2 116.3(2) . . ?
C3 C2 C7 119.4(2) . . ?
C3 C2 C1 119.6(2) . . ?
C7 C2 C1 121.0(2) . . ?
C6 C7 C2 120.7(2) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
O3 C4 C3 119.4(2) . . ?
O3 C4 C5 120.1(2) . . ?
C3 C4 C5 120.4(2) . . ?
C1 O1 H1A 113(2) . . ?

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
C16 C15 O6 C10 -177.0(2) . . . . ?
C11 C12 C13 C14 1.4(5) . . . . ?
C13 C12 C11 C10 0.1(5) . . . . ?
C12 C13 C14 C9 -2.0(4) . . . . ?
C7 C6 C5 O4 -179.5(2) . . . . ?
C7 C6 C5 C4 1.1(4) . . . . ?
C15 O6 C10 C11 5.1(4) . . . . ?
C15 O6 C10 C9 -175.6(2) . . . . ?
C12 C11 C10 O6 178.1(3) . . . . ?
C12 C11 C10 C9 -1.2(4) . . . . ?
C13 C14 C9 C10 0.9(4) . . . . ?
C13 C14 C9 C8 178.7(3) . . . . ?
O6 C10 C9 C14 -178.6(2) . . . . ?
C11 C10 C9 C14 0.7(4) . . . . ?
O6 C10 C9 C8 3.8(4) . . . . ?
C11 C10 C9 C8 -176.9(3) . . . . ?
C14 C9 C8 O5 2.7(4) . . . . ?
C10 C9 C8 O5 -179.7(3) . . . . ?
C14 C9 C8 N2 -177.7(3) . . . . ?
C10 C9 C8 N2 -0.1(4) . . . . ?
O2 C1 C2 C3 -1.0(4) . . . . ?
O1 C1 C2 C3 178.2(2) . . . . ?
O2 C1 C2 C7 179.5(2) . . . . ?
O1 C1 C2 C7 -1.3(4) . . . . ?
C5 C6 C7 C2 -1.0(4) . . . . ?
C3 C2 C7 C6 0.1(4) . . . . ?
C1 C2 C7 C6 179.6(2) . . . . ?
C7 C2 C3 C4 0.5(4) . . . . ?
C1 C2 C3 C4 -179.0(2) . . . . ?
C2 C3 C4 O3 -178.4(2) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
O4 C5 C4 O3 -1.8(4) . . . . ?
C6 C5 C4 O3 177.6(2) . . . . ?
O4 C5 C4 C3 -179.9(2) . . . . ?
C6 C5 C4 C3 -0.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.942
_diffrn_reflns_theta_full        31.87
_diffrn_measured_fraction_theta_full 0.942
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.083
####################################################################### 
# 
# 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_zmd26dhba
_database_code_depnum_ccdc_archive 'CCDC 1522936'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2017-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N O6'
_chemical_formula_weight         319.31

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   P2(1)/n

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

_cell_length_a                   7.3291(3)
_cell_length_b                   13.5985(5)
_cell_length_c                   14.7837(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.570(3)
_cell_angle_gamma                90.00
_cell_volume                     1466.46(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3273
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      26.11

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9484
_exptl_absorpt_correction_T_max  0.9856
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11403
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         26.39
_reflns_number_total             2938
_reflns_number_gt                2394
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0617P)²+0.0971P] 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         2938
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
C2 C 0.35893(18) 0.67788(10) 0.34060(9) 0.0153(3) Uani 1 1 d . . .
C11 C 0.07984(19) 0.19813(11) 0.74104(10) 0.0201(3) Uani 1 1 d . . .
H11 H 0.0715 0.1284 0.7416 0.024 Uiso 1 1 calc R . .
C10 C 0.12889(18) 0.24622(11) 0.66384(9) 0.0166(3) Uani 1 1 d . . .
C14 C 0.09952(19) 0.40119(11) 0.74053(9) 0.0198(3) Uani 1 1 d . . .
H14 H 0.1051 0.4710 0.7405 0.024 Uiso 1 1 calc R . .
C5 C 0.44210(19) 0.82573(11) 0.21998(9) 0.0199(3) Uani 1 1 d . . .
H5 H 0.4711 0.8761 0.1792 0.024 Uiso 1 1 calc R . .
C9 C 0.13766(18) 0.34986(10) 0.66262(9) 0.0162(3) Uani 1 1 d . . .
C3 C 0.34606(19) 0.77825(10) 0.36417(9) 0.0171(3) Uani 1 1 d . . .
C4 C 0.38664(19) 0.85145(10) 0.30366(9) 0.0195(3) Uani 1 1 d . . .
H4 H 0.3764 0.9187 0.3196 0.023 Uiso 1 1 calc R . .
C8 C 0.18722(18) 0.40970(10) 0.58450(9) 0.0158(3) Uani 1 1 d . . .
C1 C 0.31655(19) 0.59797(10) 0.40266(9) 0.0164(3) Uani 1 1 d . . .
C12 C 0.04333(19) 0.25141(12) 0.81669(9) 0.0225(3) Uani 1 1 d . . .
H12 H 0.0103 0.2178 0.8690 0.027 Uiso 1 1 calc R . .
C7 C 0.41440(18) 0.65460(10) 0.25412(9) 0.0167(3) Uani 1 1 d . . .
C16 C 0.2550(2) 0.05762(11) 0.50611(10) 0.0252(4) Uani 1 1 d . . .
H16A H 0.1848 0.0836 0.4515 0.038 Uiso 1 1 calc R . .
H16B H 0.2551 -0.0144 0.5037 0.038 Uiso 1 1 calc R . .
H16C H 0.3814 0.0818 0.5090 0.038 Uiso 1 1 calc R . .
C15 C 0.1690(2) 0.09100(10) 0.58880(9) 0.0208(3) Uani 1 1 d . . .
H15A H 0.0415 0.0664 0.5871 0.025 Uiso 1 1 calc R . .
H15B H 0.2394 0.0659 0.6446 0.025 Uiso 1 1 calc R . .
C13 C 0.0540(2) 0.35323(11) 0.81759(9) 0.0222(4) Uani 1 1 d . . .
H13 H 0.0305 0.3893 0.8702 0.027 Uiso 1 1 calc R . .
C6 C 0.45619(19) 0.72837(11) 0.19447(9) 0.0199(3) Uani 1 1 d . . .
H6 H 0.4941 0.7121 0.1367 0.024 Uiso 1 1 calc R . .
O6 O 0.17101(14) 0.19763(6) 0.58791(6) 0.0196(3) Uani 1 1 d . . .
O4 O 0.42880(14) 0.55999(7) 0.22655(7) 0.0221(3) Uani 1 1 d . . .
O2 O 0.26302(14) 0.62361(7) 0.48094(6) 0.0200(3) Uani 1 1 d . . .
O3 O 0.29401(15) 0.80782(8) 0.44550(7) 0.0233(3) Uani 1 1 d . . .
O1 O 0.33075(14) 0.50985(7) 0.38110(6) 0.0220(3) Uani 1 1 d . . .
N1 N 0.23795(17) 0.36741(10) 0.51073(8) 0.0193(3) Uani 1 1 d . . .
O5 O 0.18033(14) 0.50240(7) 0.59152(7) 0.0239(3) Uani 1 1 d . . .
H1A H 0.238(2) 0.3009(14) 0.5104(11) 0.036(5) Uiso 1 1 d . . .
H1B H 0.269(2) 0.4041(13) 0.4649(11) 0.030(5) Uiso 1 1 d . . .
H4A H 0.394(3) 0.5253(15) 0.2752(15) 0.066(7) Uiso 1 1 d . . .
H3A H 0.276(2) 0.7549(17) 0.4744(13) 0.047(6) Uiso 1 1 d . . .
H2A H 0.237(3) 0.5606(17) 0.5255(14) 0.069(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
C2 C3 1.4141(19) . ?
C2 C7 1.4145(18) . ?
C2 C1 1.4746(19) . ?
C11 C12 1.380(2) . ?
C11 C10 1.3924(19) . ?
C11 H11 0.9500 . ?
C10 O6 1.3634(16) . ?
C10 C9 1.411(2) . ?
C14 C13 1.3815(19) . ?
C14 C9 1.3979(19) . ?
C14 H14 0.9500 . ?
C5 C4 1.3840(19) . ?
C5 C6 1.383(2) . ?
C5 H5 0.9500 . ?
C9 C8 1.4863(18) . ?
C3 O3 1.3572(16) . ?
C3 C4 1.390(2) . ?
C4 H4 0.9500 . ?
C8 O5 1.2663(16) . ?
C8 N1 1.3180(17) . ?
C1 O1 1.2470(16) . ?
C1 O2 1.3049(16) . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C7 O4 1.3567(17) . ?
C7 C6 1.389(2) . ?
C16 C15 1.4992(19) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C15 O6 1.4502(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C13 H13 0.9500 . ?
C6 H6 0.9500 . ?
O4 H4A 0.92(2) . ?
O2 H2A 1.11(2) . ?
O3 H3A 0.85(2) . ?
N1 H1A 0.904(18) . ?
N1 H1B 0.889(17) . ?
O5 H2A 1.35(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C7 118.08(12) . . ?
C3 C2 C1 122.33(12) . . ?
C7 C2 C1 119.59(13) . . ?
C12 C11 C10 120.23(14) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
O6 C10 C11 122.98(13) . . ?
O6 C10 C9 117.34(11) . . ?
C11 C10 C9 119.68(12) . . ?
C13 C14 C9 121.82(14) . . ?
C13 C14 H14 119.1 . . ?
C9 C14 H14 119.1 . . ?
C4 C5 C6 121.45(13) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C14 C9 C10 118.37(12) . . ?
C14 C9 C8 116.76(13) . . ?
C10 C9 C8 124.86(12) . . ?
O3 C3 C4 117.01(13) . . ?
O3 C3 C2 122.38(12) . . ?
C4 C3 C2 120.61(13) . . ?
C5 C4 C3 119.61(13) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
O5 C8 N1 121.26(13) . . ?
O5 C8 C9 117.81(11) . . ?
N1 C8 C9 120.93(13) . . ?
O1 C1 O2 121.55(12) . . ?
O1 C1 C2 121.42(12) . . ?
O2 C1 C2 117.03(12) . . ?
C11 C12 C13 121.10(13) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
O4 C7 C6 117.75(13) . . ?
O4 C7 C2 121.42(12) . . ?
C6 C7 C2 120.83(13) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O6 C15 C16 106.85(11) . . ?
O6 C15 H15A 110.4 . . ?
C16 C15 H15A 110.4 . . ?
O6 C15 H15B 110.4 . . ?
C16 C15 H15B 110.4 . . ?
H15A C15 H15B 108.6 . . ?
C14 C13 C12 118.78(13) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C5 C6 C7 119.41(13) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C10 O6 C15 118.28(10) . . ?
C7 O4 H4A 102.5(13) . . ?
C1 O2 H2A 113.9(11) . . ?
C3 O3 H3A 105.3(13) . . ?
C8 N1 H1A 116.1(11) . . ?
C8 N1 H1B 120.0(11) . . ?
H1A N1 H1B 123.9(15) . . ?
C8 O5 H2A 120.4(9) . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        26.39
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.061
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zmd35dhba
_database_code_depnum_ccdc_archive 'CCDC 1522941'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2017-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H33 N O16'
_chemical_formula_weight         663.57

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

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

_cell_length_a                   11.278(11)
_cell_length_b                   11.819(9)
_cell_length_c                   12.258(10)
_cell_angle_alpha                95.27(3)
_cell_angle_beta                 102.49(4)
_cell_angle_gamma                100.87(4)
_cell_volume                     1552(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    442
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      19.99

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9614
_exptl_absorpt_correction_T_max  0.9759
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5480
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_sigmaI/netI    0.1057
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       14
_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         2.23
_diffrn_reflns_theta_max         27.06
_reflns_number_total             4456
_reflns_number_gt                1889
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0825P)²+0.0000P] 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       0.0045(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4456
_refine_ls_number_parameters     486
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1583
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.1943
_refine_ls_wR_factor_gt          0.1439
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_restrained_S_all      0.911
_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
O6 O 0.1422(4) -0.1523(4) 0.7754(3) 0.0824(17) Uani 1 1 d . . .
O5 O 0.2818(3) -0.1156(3) 0.9388(3) 0.0671(13) Uani 1 1 d . . .
O13 O 0.1227(4) 0.2081(3) 0.6090(3) 0.0604(12) Uani 1 1 d . . .
O12 O 0.2786(3) 0.4097(3) 0.3952(3) 0.0667(13) Uani 1 1 d . . .
O2 O 0.1298(3) 0.0897(3) -0.0312(3) 0.0614(12) Uani 1 1 d . . .
O1 O 0.1057(4) 0.0140(4) 0.1251(3) 0.0678(13) Uani 1 1 d . . .
C3 C 0.3378(5) 0.1429(5) 0.2473(4) 0.0462(16) Uani 1 1 d . . .
H3 H 0.2876 0.0993 0.2862 0.055 Uiso 1 1 calc R . .
O3 O 0.4902(4) 0.2070(4) 0.4184(3) 0.0615(14) Uani 1 1 d . . .
O4 O 0.5608(4) 0.3348(4) 0.0709(3) 0.0749(15) Uani 1 1 d . . .
O9 O 0.2192(4) 0.4168(3) 1.1750(3) 0.0556(12) Uani 1 1 d . . .
O11 O 0.1970(3) 0.5567(3) 0.8040(3) 0.0675(13) Uani 1 1 d . . .
O10 O 0.0445(3) 0.2832(3) 1.1579(3) 0.0609(12) Uani 1 1 d . . .
C11 C 0.5280(5) 0.1032(5) 0.7929(4) 0.0487(16) Uani 1 1 d . . .
C8 C 0.2545(5) -0.1026(5) 0.8407(4) 0.0509(16) Uani 1 1 d . . .
C29 C 0.0632(5) 0.1445(5) 0.6855(4) 0.0612(18) Uani 1 1 d . . .
H29A H 0.0605 0.1973 0.7500 0.073 Uiso 1 1 calc R . .
H29B H 0.1090 0.0868 0.7125 0.073 Uiso 1 1 calc R . .
C27 C 0.3012(6) 0.2920(5) 0.7628(4) 0.0608(18) Uani 1 1 d . . .
H27 H 0.2644 0.2516 0.8128 0.073 Uiso 1 1 calc R . .
C26 C 0.4168(6) 0.3635(6) 0.8005(4) 0.0672(19) Uani 1 1 d . . .
H26 H 0.4586 0.3703 0.8758 0.081 Uiso 1 1 calc R . .
C25 C 0.4724(5) 0.4263(5) 0.7267(4) 0.0669(19) Uani 1 1 d . . .
H25 H 0.5503 0.4758 0.7524 0.080 Uiso 1 1 calc R . .
C22 C 0.2351(6) 0.3343(6) 0.4520(4) 0.0538(18) Uani 1 1 d . . .
N1 N 0.1387(6) 0.2499(6) 0.4016(4) 0.080(2) Uani 1 1 d . . .
C6 C 0.4893(5) 0.2722(5) 0.1322(4) 0.0506(16) Uani 1 1 d . . .
C5 C 0.5302(5) 0.2738(4) 0.2469(4) 0.0463(15) Uani 1 1 d . . .
H5 H 0.6076 0.3182 0.2856 0.056 Uiso 1 1 calc R . .
C19 C -0.0005(5) 0.4249(5) 0.7789(4) 0.0531(17) Uani 1 1 d . . .
H19 H -0.0257 0.4412 0.7057 0.064 Uiso 1 1 calc R . .
C18 C 0.1168(5) 0.4775(5) 0.8443(4) 0.0474(16) Uani 1 1 d . . .
C12 C 0.4976(5) 0.1022(5) 0.6775(4) 0.0521(17) Uani 1 1 d . . .
H12 H 0.5522 0.1461 0.6426 0.062 Uiso 1 1 calc R . .
C14 C 0.3038(5) -0.0324(5) 0.6662(4) 0.0521(16) Uani 1 1 d . . .
H14 H 0.2288 -0.0779 0.6234 0.062 Uiso 1 1 calc R . .
C13 C 0.3855(5) 0.0356(5) 0.6140(4) 0.0514(17) Uani 1 1 d . . .
O7 O 0.6413(4) 0.1719(4) 0.8520(3) 0.0720(15) Uani 1 1 d . . .
C28 C 0.2391(5) 0.2799(5) 0.6504(4) 0.0471(16) Uani 1 1 d . . .
C24 C 0.4100(5) 0.4136(5) 0.6157(4) 0.0560(17) Uani 1 1 d . . .
H24 H 0.4473 0.4547 0.5664 0.067 Uiso 1 1 calc R . .
C23 C 0.2928(5) 0.3414(5) 0.5739(4) 0.0479(16) Uani 1 1 d . . .
C1 C 0.1698(5) 0.0779(5) 0.0722(4) 0.0472(16) Uani 1 1 d . . .
C2 C 0.2971(5) 0.1436(4) 0.1323(4) 0.0413(14) Uani 1 1 d . . .
C7 C 0.3733(5) 0.2097(5) 0.0744(4) 0.0489(16) Uani 1 1 d . . .
H7 H 0.3457 0.2114 -0.0025 0.059 Uiso 1 1 calc R . .
C4 C 0.4543(5) 0.2082(5) 0.3037(4) 0.0453(15) Uani 1 1 d . . .
C20 C -0.0805(5) 0.3475(5) 0.8233(4) 0.0452(15) Uani 1 1 d . . .
C21 C -0.0438(5) 0.3214(5) 0.9321(4) 0.0454(15) Uani 1 1 d . . .
H21 H -0.0967 0.2684 0.9609 0.055 Uiso 1 1 calc R . .
C16 C 0.0733(5) 0.3762(4) 0.9966(4) 0.0412(15) Uani 1 1 d . . .
C15 C 0.1106(5) 0.3535(5) 1.1164(4) 0.0457(16) Uani 1 1 d . . .
C17 C 0.1554(5) 0.4547(4) 0.9533(4) 0.0475(15) Uani 1 1 d . . .
H17 H 0.2340 0.4904 0.9972 0.057 Uiso 1 1 calc R . .
C9 C 0.3364(5) -0.0307(5) 0.7818(4) 0.0428(15) Uani 1 1 d . . .
C10 C 0.4486(5) 0.0374(5) 0.8459(4) 0.0440(15) Uani 1 1 d . . .
H10 H 0.4701 0.0385 0.9237 0.053 Uiso 1 1 calc R . .
O15 O 0.2909(4) 0.6427(4) 0.4620(3) 0.0702(13) Uani 1 1 d D . .
O14 O -0.1960(4) 0.2971(4) 0.7544(3) 0.0659(13) Uani 1 1 d . . .
O8 O 0.3502(4) 0.0309(4) 0.4997(3) 0.0823(16) Uani 1 1 d . . .
O16 O 0.1073(6) 0.5902(6) 0.5856(5) 0.115(2) Uani 1 1 d D . .
C30 C -0.0657(6) 0.0866(6) 0.6208(5) 0.080(2) Uani 1 1 d . . .
H30A H -0.1100 0.1446 0.5947 0.120 Uiso 1 1 calc R . .
H30B H -0.1082 0.0434 0.6688 0.120 Uiso 1 1 calc R . .
H30C H -0.0618 0.0347 0.5573 0.120 Uiso 1 1 calc R . .
H1A H 0.105(5) 0.249(5) 0.317(5) 0.087(18) Uiso 1 1 d . . .
H14A H -0.243(4) 0.248(4) 0.796(4) 0.050(15) Uiso 1 1 d . . .
H7A H 0.656(5) 0.166(5) 0.923(5) 0.09(2) Uiso 1 1 d . . .
H6A H 0.095(6) -0.202(5) 0.805(5) 0.09(2) Uiso 1 1 d . . .
H11A H 0.172(5) 0.562(5) 0.729(5) 0.09(2) Uiso 1 1 d . . .
H15A H 0.273(5) 0.663(5) 0.398(2) 0.076(19) Uiso 1 1 d D . .
H8A H 0.404(7) 0.094(7) 0.479(6) 0.14(3) Uiso 1 1 d . . .
H4A H 0.629(6) 0.372(6) 0.119(5) 0.09(2) Uiso 1 1 d . . .
H9A H 0.235(8) 0.404(7) 1.246(7) 0.16(3) Uiso 1 1 d . . .
H1B H 0.096(5) 0.196(5) 0.440(5) 0.08(2) Uiso 1 1 d . . .
H2A H 0.004(10) -0.040(8) 0.076(7) 0.21(4) Uiso 1 1 d . . .
H3A H 0.550(6) 0.260(6) 0.459(5) 0.10(3) Uiso 1 1 d . . .
H16B H 0.160(5) 0.612(6) 0.549(6) 0.15(4) Uiso 1 1 d D . .
H16A H 0.057(4) 0.635(4) 0.575(4) 0.04(2) Uiso 1 1 d D . .
H15B H 0.224(6) 0.63(2) 0.484(11) 0.63(18) Uiso 1 1 d 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
O6 C8 1.335(6) . ?
O6 H6A 0.88(6) . ?
O5 C8 1.207(5) . ?
O13 C28 1.383(6) . ?
O13 C29 1.452(5) . ?
O12 C22 1.271(6) . ?
O2 C1 1.280(5) . ?
O1 C1 1.264(6) . ?
O1 H2A 1.20(11) . ?
C3 C2 1.386(6) . ?
C3 C4 1.388(6) . ?
C3 H3 0.9300 . ?
O3 C4 1.379(5) . ?
O3 H3A 0.86(7) . ?
O4 C6 1.378(6) . ?
O4 H4A 0.88(6) . ?
O9 C15 1.323(6) . ?
O9 H9A 0.88(8) . ?
O11 C18 1.378(5) . ?
O11 H11A 0.91(6) . ?
O10 C15 1.231(6) . ?
C11 C12 1.380(6) . ?
C11 C10 1.382(6) . ?
C11 O7 1.384(6) . ?
C8 C9 1.484(7) . ?
C29 C30 1.496(7) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C27 C26 1.371(7) . ?
C27 C28 1.385(6) . ?
C27 H27 0.9300 . ?
C26 C25 1.399(7) . ?
C26 H26 0.9300 . ?
C25 C24 1.370(7) . ?
C25 H25 0.9300 . ?
C22 N1 1.321(7) . ?
C22 C23 1.483(6) . ?
N1 H1A 1.03(6) . ?
N1 H1B 0.94(6) . ?
C6 C7 1.378(7) . ?
C6 C5 1.378(6) . ?
C5 C4 1.388(6) . ?
C5 H5 0.9300 . ?
C19 C18 1.385(7) . ?
C19 C20 1.393(6) . ?
C19 H19 0.9300 . ?
C18 C17 1.380(6) . ?
C12 C13 1.382(7) . ?
C12 H12 0.9300 . ?
C14 C9 1.382(6) . ?
C14 C13 1.404(6) . ?
C14 H14 0.9300 . ?
C13 O8 1.365(5) . ?
O7 H7A 0.87(6) . ?
C28 C23 1.407(6) . ?
C24 C23 1.392(7) . ?
C24 H24 0.9300 . ?
C1 C2 1.491(7) . ?
C2 C7 1.402(6) . ?
C7 H7 0.9300 . ?
C20 O14 1.380(6) . ?
C20 C21 1.388(6) . ?
C21 C16 1.386(6) . ?
C21 H21 0.9300 . ?
C16 C17 1.407(6) . ?
C16 C15 1.501(6) . ?
C17 H17 0.9300 . ?
C9 C10 1.391(7) . ?
C10 H10 0.9300 . ?
O15 H15A 0.833(10) . ?
O15 H15B 0.840(11) . ?
O14 H14A 0.96(5) . ?
O8 H8A 0.96(8) . ?
O16 H16B 0.841(11) . ?
O16 H16A 0.839(10) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 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
C8 O6 H6A 116(4) . . ?
C28 O13 C29 119.2(4) . . ?
C1 O1 H2A 119(4) . . ?
C2 C3 C4 119.2(4) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C4 O3 H3A 120(4) . . ?
C6 O4 H4A 107(4) . . ?
C15 O9 H9A 112(5) . . ?
C18 O11 H11A 115(4) . . ?
C12 C11 C10 121.0(5) . . ?
C12 C11 O7 117.0(4) . . ?
C10 C11 O7 122.0(4) . . ?
O5 C8 O6 120.9(5) . . ?
O5 C8 C9 125.2(5) . . ?
O6 C8 C9 113.8(4) . . ?
O13 C29 C30 107.0(4) . . ?
O13 C29 H29A 110.3 . . ?
C30 C29 H29A 110.3 . . ?
O13 C29 H29B 110.3 . . ?
C30 C29 H29B 110.3 . . ?
H29A C29 H29B 108.6 . . ?
C26 C27 C28 120.1(5) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C26 C25 120.6(5) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C24 C25 C26 118.7(6) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
O12 C22 N1 119.5(5) . . ?
O12 C22 C23 119.9(6) . . ?
N1 C22 C23 120.5(5) . . ?
C22 N1 H1A 116(3) . . ?
C22 N1 H1B 124(4) . . ?
H1A N1 H1B 119(5) . . ?
C7 C6 O4 117.1(4) . . ?
C7 C6 C5 121.0(5) . . ?
O4 C6 C5 121.8(5) . . ?
C6 C5 C4 119.1(5) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C18 C19 C20 119.7(4) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
O11 C18 C17 118.0(5) . . ?
O11 C18 C19 121.1(4) . . ?
C17 C18 C19 120.9(5) . . ?
C11 C12 C13 119.6(5) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C9 C14 C13 119.1(5) . . ?
C9 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
O8 C13 C12 122.4(4) . . ?
O8 C13 C14 117.3(5) . . ?
C12 C13 C14 120.3(4) . . ?
C11 O7 H7A 112(4) . . ?
O13 C28 C27 121.9(5) . . ?
O13 C28 C23 117.4(4) . . ?
C27 C28 C23 120.7(5) . . ?
C25 C24 C23 122.5(5) . . ?
C25 C24 H24 118.8 . . ?
C23 C24 H24 118.8 . . ?
C24 C23 C28 117.4(4) . . ?
C24 C23 C22 117.4(5) . . ?
C28 C23 C22 125.2(5) . . ?
O1 C1 O2 122.8(5) . . ?
O1 C1 C2 119.1(4) . . ?
O2 C1 C2 118.1(5) . . ?
C3 C2 C7 120.0(5) . . ?
C3 C2 C1 119.4(4) . . ?
C7 C2 C1 120.5(4) . . ?
C6 C7 C2 119.5(4) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
O3 C4 C5 121.5(5) . . ?
O3 C4 C3 117.3(4) . . ?
C5 C4 C3 121.1(4) . . ?
O14 C20 C21 121.9(4) . . ?
O14 C20 C19 117.3(4) . . ?
C21 C20 C19 120.9(5) . . ?
C16 C21 C20 118.6(4) . . ?
C16 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C21 C16 C17 121.4(4) . . ?
C21 C16 C15 118.8(4) . . ?
C17 C16 C15 119.8(5) . . ?
O10 C15 O9 122.4(4) . . ?
O10 C15 C16 122.7(5) . . ?
O9 C15 C16 114.9(5) . . ?
C18 C17 C16 118.6(5) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C14 C9 C10 120.5(4) . . ?
C14 C9 C8 121.3(5) . . ?
C10 C9 C8 118.2(4) . . ?
C11 C10 C9 119.4(4) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
H15A O15 H15B 106(3) . . ?
C20 O14 H14A 109(3) . . ?
C13 O8 H8A 107(4) . . ?
H16B O16 H16A 105(3) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
C28 O13 C29 C30 173.3(5) . . . . ?
C28 C27 C26 C25 1.1(10) . . . . ?
C27 C26 C25 C24 -1.0(10) . . . . ?
C7 C6 C5 C4 2.1(9) . . . . ?
O4 C6 C5 C4 -179.5(5) . . . . ?
C20 C19 C18 O11 -178.4(5) . . . . ?
C20 C19 C18 C17 -0.3(9) . . . . ?
C10 C11 C12 C13 0.9(9) . . . . ?
O7 C11 C12 C13 -179.8(5) . . . . ?
C11 C12 C13 O8 -179.9(5) . . . . ?
C11 C12 C13 C14 -1.2(9) . . . . ?
C9 C14 C13 O8 179.6(5) . . . . ?
C9 C14 C13 C12 0.8(9) . . . . ?
C29 O13 C28 C27 0.6(8) . . . . ?
C29 O13 C28 C23 -179.0(5) . . . . ?
C26 C27 C28 O13 179.6(6) . . . . ?
C26 C27 C28 C23 -0.8(9) . . . . ?
C26 C25 C24 C23 0.7(10) . . . . ?
C25 C24 C23 C28 -0.4(9) . . . . ?
C25 C24 C23 C22 -179.6(6) . . . . ?
O13 C28 C23 C24 -179.9(5) . . . . ?
C27 C28 C23 C24 0.4(9) . . . . ?
O13 C28 C23 C22 -0.8(9) . . . . ?
C27 C28 C23 C22 179.6(6) . . . . ?
O12 C22 C23 C24 -15.0(9) . . . . ?
N1 C22 C23 C24 164.9(6) . . . . ?
O12 C22 C23 C28 165.8(6) . . . . ?
N1 C22 C23 C28 -14.3(10) . . . . ?
C4 C3 C2 C7 -0.1(8) . . . . ?
C4 C3 C2 C1 -177.2(5) . . . . ?
O1 C1 C2 C3 -6.6(8) . . . . ?
O2 C1 C2 C3 172.8(5) . . . . ?
O1 C1 C2 C7 176.2(5) . . . . ?
O2 C1 C2 C7 -4.3(8) . . . . ?
O4 C6 C7 C2 179.4(5) . . . . ?
C5 C6 C7 C2 -2.1(9) . . . . ?
C3 C2 C7 C6 1.1(8) . . . . ?
C1 C2 C7 C6 178.3(5) . . . . ?
C6 C5 C4 O3 -179.7(5) . . . . ?
C6 C5 C4 C3 -1.0(8) . . . . ?
C2 C3 C4 O3 178.8(5) . . . . ?
C2 C3 C4 C5 0.0(8) . . . . ?
C18 C19 C20 O14 -179.7(5) . . . . ?
C18 C19 C20 C21 -0.6(9) . . . . ?
O14 C20 C21 C16 -179.5(5) . . . . ?
C19 C20 C21 C16 1.4(8) . . . . ?
C20 C21 C16 C17 -1.4(8) . . . . ?
C20 C21 C16 C15 176.6(5) . . . . ?
C21 C16 C15 O10 4.3(8) . . . . ?
C17 C16 C15 O10 -177.7(5) . . . . ?
C21 C16 C15 O9 -174.3(5) . . . . ?
C17 C16 C15 O9 3.7(8) . . . . ?
O11 C18 C17 C16 178.4(5) . . . . ?
C19 C18 C17 C16 0.4(8) . . . . ?
C21 C16 C17 C18 0.5(8) . . . . ?
C15 C16 C17 C18 -177.4(5) . . . . ?
C13 C14 C9 C10 0.0(8) . . . . ?
C13 C14 C9 C8 -178.9(5) . . . . ?
O5 C8 C9 C14 171.6(6) . . . . ?
O6 C8 C9 C14 -9.8(8) . . . . ?
O5 C8 C9 C10 -7.2(9) . . . . ?
O6 C8 C9 C10 171.4(5) . . . . ?
C12 C11 C10 C9 -0.1(9) . . . . ?
O7 C11 C10 C9 -179.5(5) . . . . ?
C14 C9 C10 C11 -0.3(8) . . . . ?
C8 C9 C10 C11 178.6(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.654
_diffrn_reflns_theta_full        27.06
_diffrn_measured_fraction_theta_full 0.654
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.057
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol chlorofrom'
