# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_20
_database_code_depnum_ccdc_archive 'CCDC 1916072'
loop_
_audit_author_name
_audit_author_address
'ALEXANDRA MARTHA ZOYA Slawin' 'University of St Andrews'
_audit_update_record             
;
2019-05-14 deposited with the CCDC.	2019-09-12 downloaded from the CCDC.
;
_audit_creation_date             2017-09-26
_audit_creation_method           'by CrystalStructure 4.2'


_chemical_formula_sum            'C17 H21 N O4'
_chemical_formula_moiety         'C17 H21 N O4'
_chemical_formula_weight         303.36
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   15.59060(16)
_cell_length_b                   5.83233(5)
_cell_length_c                   19.3142(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 112.9800(13)
_cell_angle_gamma                90.0000
_cell_volume                     1616.86(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13929
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      75.25
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648.00
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.8d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.743
_exptl_absorpt_correction_T_max  0.978

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            17824
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_theta_max         75.426
_diffrn_reflns_theta_min         3.112
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3279
_reflns_number_gt                3142
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1119
_refine_ls_wR_factor_gt          0.1111
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3279
_refine_ls_number_parameters     204
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0654P)²+0.6680P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0085(7)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O2 O 0.40459(5) 0.66638(14) 0.43286(4) 0.0174(2) Uani 1 1 d . . . . .
O4 O 0.34181(7) 1.10946(19) 0.61062(5) 0.0396(3) Uani 1 1 d . . . . .
O10 O 0.16242(5) 0.92248(15) 0.44300(5) 0.0232(2) Uani 1 1 d . . . . .
O11 O 0.23637(5) 0.60124(14) 0.50146(5) 0.0220(2) Uani 1 1 d . . . . .
N1 N 0.45508(6) 0.66331(16) 0.56145(5) 0.0155(2) Uani 1 1 d D . . . .
C2 C 0.39959(7) 0.73036(18) 0.49199(6) 0.0135(2) Uani 1 1 d . . . . .
C3 C 0.33054(7) 0.91053(18) 0.49650(6) 0.0144(2) Uani 1 1 d . . . . .
C4 C 0.36601(8) 0.9539(2) 0.58162(6) 0.0207(3) Uani 1 1 d . . . . .
C5 C 0.43888(7) 0.7739(2) 0.62307(6) 0.0172(2) Uani 1 1 d . . . . .
H5 H 0.4121 0.6610 0.6481 0.021 Uiso 1 1 calc R U . . .
C6 C 0.52538(7) 0.88661(19) 0.68141(6) 0.0178(2) Uani 1 1 d . . . . .
H6A H 0.5074 0.9622 0.7196 0.021 Uiso 1 1 calc R U . . .
H6B H 0.5470 1.0078 0.6561 0.021 Uiso 1 1 calc R U . . .
C7 C 0.60697(7) 0.7247(2) 0.72181(6) 0.0180(2) Uani 1 1 d . . . . .
H7 H 0.6317 0.6678 0.6844 0.022 Uiso 1 1 calc R U . . .
C8 C 0.68383(8) 0.8610(2) 0.78206(7) 0.0264(3) Uani 1 1 d . . . . .
H8A H 0.7013 0.9925 0.7588 0.032 Uiso 1 1 calc R U . . .
H8B H 0.6612 0.9156 0.8199 0.032 Uiso 1 1 calc R U . . .
H8C H 0.7383 0.7624 0.8062 0.032 Uiso 1 1 calc R U . . .
C9 C 0.57786(10) 0.5186(2) 0.75582(7) 0.0299(3) Uani 1 1 d . . . . .
H9A H 0.5286 0.4342 0.7161 0.036 Uiso 1 1 calc R U . . .
H9B H 0.6317 0.4178 0.7798 0.036 Uiso 1 1 calc R U . . .
H9C H 0.5546 0.5710 0.7935 0.036 Uiso 1 1 calc R U . . .
C10 C 0.23230(7) 0.81398(19) 0.47505(6) 0.0152(2) Uani 1 1 d . . . . .
C12 C 0.14812(9) 0.4996(2) 0.49765(8) 0.0269(3) Uani 1 1 d . . . . .
H12A H 0.1512 0.3305 0.4947 0.032 Uiso 1 1 calc R U . . .
H12B H 0.0961 0.5547 0.4520 0.032 Uiso 1 1 calc R U . . .
C13 C 0.13146(8) 0.5668(2) 0.56658(7) 0.0231(3) Uani 1 1 d . . . . .
C14 C 0.07718(10) 0.7559(2) 0.56505(8) 0.0318(3) Uani 1 1 d . . . . .
H14 H 0.0487 0.8405 0.5198 0.038 Uiso 1 1 calc R U . . .
C15 C 0.06397(11) 0.8228(3) 0.62916(9) 0.0370(3) Uani 1 1 d . . . . .
H15 H 0.0262 0.9522 0.6274 0.044 Uiso 1 1 calc R U . . .
C16 C 0.10565(10) 0.7020(3) 0.69550(8) 0.0344(3) Uani 1 1 d . . . . .
H16 H 0.0971 0.7490 0.7395 0.041 Uiso 1 1 calc R U . . .
C17 C 0.15951(12) 0.5137(3) 0.69760(9) 0.0478(4) Uani 1 1 d . . . . .
H17 H 0.1880 0.4298 0.7430 0.057 Uiso 1 1 calc R U . . .
C18 C 0.17240(11) 0.4456(3) 0.63345(10) 0.0420(4) Uani 1 1 d . . . . .
H18 H 0.2096 0.3149 0.6353 0.050 Uiso 1 1 calc R U . . .
C19 C 0.33020(8) 1.12572(19) 0.45183(7) 0.0221(3) Uani 1 1 d . . . . .
H19A H 0.3941 1.1828 0.4669 0.027 Uiso 1 1 calc R U . . .
H19B H 0.3047 1.0894 0.3980 0.027 Uiso 1 1 calc R U . . .
H19C H 0.2916 1.2435 0.4618 0.027 Uiso 1 1 calc R U . . .
H1 H 0.5016(9) 0.545(2) 0.5675(9) 0.032(4) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
O2 C2 1.2323(13) . ?
O4 C4 1.2018(15) . ?
O10 C10 1.2016(14) . ?
O11 C10 1.3336(14) . ?
O11 C12 1.4733(13) . ?
N1 C2 1.3397(14) . ?
N1 C5 1.4599(13) . ?
N1 H1 0.974(5) . ?
C2 C3 1.5311(13) . ?
C3 C19 1.5218(15) . ?
C3 C10 1.5294(14) . ?
C3 C4 1.5371(15) . ?
C4 C5 1.5241(15) . ?
C5 C6 1.5277(15) . ?
C5 H5 1.0000 . ?
C6 C7 1.5310(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C9 1.5216(16) . ?
C7 C8 1.5276(16) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C12 C13 1.5046(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.3831(17) . ?
C13 C18 1.390(2) . ?
C14 C15 1.3882(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.374(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O11 C12 116.81(9) . . ?
C2 N1 C5 115.97(9) . . ?
C2 N1 H1 119.0(9) . . ?
C5 N1 H1 125.0(9) . . ?
O2 C2 N1 126.15(9) . . ?
O2 C2 C3 124.11(9) . . ?
N1 C2 C3 109.68(9) . . ?
C19 C3 C10 111.63(9) . . ?
C19 C3 C2 112.37(9) . . ?
C10 C3 C2 112.58(8) . . ?
C19 C3 C4 113.01(9) . . ?
C10 C3 C4 104.74(8) . . ?
C2 C3 C4 101.91(8) . . ?
O4 C4 C5 125.47(10) . . ?
O4 C4 C3 125.12(11) . . ?
C5 C4 C3 109.37(9) . . ?
N1 C5 C4 101.94(8) . . ?
N1 C5 C6 114.06(8) . . ?
C4 C5 C6 110.71(9) . . ?
N1 C5 H5 110.0 . . ?
C4 C5 H5 110.0 . . ?
C6 C5 H5 110.0 . . ?
C5 C6 C7 115.41(9) . . ?
C5 C6 H6A 108.4 . . ?
C7 C6 H6A 108.4 . . ?
C5 C6 H6B 108.4 . . ?
C7 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
C9 C7 C8 111.09(9) . . ?
C9 C7 C6 112.26(10) . . ?
C8 C7 C6 108.39(9) . . ?
C9 C7 H7 108.3 . . ?
C8 C7 H7 108.3 . . ?
C6 C7 H7 108.3 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O10 C10 O11 125.82(10) . . ?
O10 C10 C3 123.80(10) . . ?
O11 C10 C3 110.23(9) . . ?
O11 C12 C13 109.36(10) . . ?
O11 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
O11 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C18 118.72(12) . . ?
C14 C13 C12 120.29(12) . . ?
C18 C13 C12 120.96(11) . . ?
C13 C14 C15 120.52(13) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 120.25(13) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 119.71(13) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.14(14) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 120.66(13) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C3 C19 H19A 109.5 . . ?
C3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C5 N1 C2 O2 176.45(10) . . . . ?
C5 N1 C2 C3 -0.73(12) . . . . ?
O2 C2 C3 C19 -49.07(14) . . . . ?
N1 C2 C3 C19 128.18(10) . . . . ?
O2 C2 C3 C10 78.00(13) . . . . ?
N1 C2 C3 C10 -104.75(10) . . . . ?
O2 C2 C3 C4 -170.33(10) . . . . ?
N1 C2 C3 C4 6.93(11) . . . . ?
C19 C3 C4 O4 46.78(16) . . . . ?
C10 C3 C4 O4 -74.95(15) . . . . ?
C2 C3 C4 O4 167.59(12) . . . . ?
C19 C3 C4 C5 -131.28(10) . . . . ?
C10 C3 C4 C5 107.00(10) . . . . ?
C2 C3 C4 C5 -10.47(11) . . . . ?
C2 N1 C5 C4 -5.87(12) . . . . ?
C2 N1 C5 C6 -125.23(10) . . . . ?
O4 C4 C5 N1 -167.97(12) . . . . ?
C3 C4 C5 N1 10.08(12) . . . . ?
O4 C4 C5 C6 -46.28(16) . . . . ?
C3 C4 C5 C6 131.77(9) . . . . ?
N1 C5 C6 C7 -60.52(13) . . . . ?
C4 C5 C6 C7 -174.78(9) . . . . ?
C5 C6 C7 C9 -52.39(13) . . . . ?
C5 C6 C7 C8 -175.48(9) . . . . ?
C12 O11 C10 O10 -6.50(16) . . . . ?
C12 O11 C10 C3 169.19(9) . . . . ?
C19 C3 C10 O10 -18.36(14) . . . . ?
C2 C3 C10 O10 -145.82(10) . . . . ?
C4 C3 C10 O10 104.27(12) . . . . ?
C19 C3 C10 O11 165.85(9) . . . . ?
C2 C3 C10 O11 38.39(12) . . . . ?
C4 C3 C10 O11 -71.52(10) . . . . ?
C10 O11 C12 C13 -86.44(13) . . . . ?
O11 C12 C13 C14 94.57(14) . . . . ?
O11 C12 C13 C18 -83.37(15) . . . . ?
C18 C13 C14 C15 0.0(2) . . . . ?
C12 C13 C14 C15 -177.97(13) . . . . ?
C13 C14 C15 C16 0.5(2) . . . . ?
C14 C15 C16 C17 -0.7(2) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C13 0.2(3) . . . . ?
C14 C13 C18 C17 -0.4(2) . . . . ?
C12 C13 C18 C17 177.60(14) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O2 . . 3_666 2.8824(13) 0.974(13) 1.915(14) 171.6(15) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_racemic26
_database_code_depnum_ccdc_archive 'CCDC 1916074'
loop_
_audit_author_name
_audit_author_address
'ALEXANDRA MARTHA ZOYA Slawin' 'University of St Andrews'
_audit_update_record             
;
2019-05-14 deposited with the CCDC.	2019-09-12 downloaded from the CCDC.
;
_audit_creation_date             2016-08-22
_audit_creation_method           'by CrystalStructure 4.2'


_chemical_formula_sum            'C28 H33 N O8'
_chemical_formula_moiety         'C28 H33 N O8'
_chemical_formula_weight         511.57
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   14.29830(9)
_cell_length_b                   10.41200(6)
_cell_length_c                   18.66340(11)
_cell_angle_alpha                90.0000
_cell_angle_beta                 105.0690(6)
_cell_angle_gamma                90.0000
_cell_volume                     2682.95(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    23392
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      75.13
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088.00
_exptl_absorpt_coefficient_mu    0.769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.700
_exptl_absorpt_correction_T_max  0.857

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            29951
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_theta_max         75.443
_diffrn_reflns_theta_min         4.512
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5454
_reflns_number_gt                5404
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.1118
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5454
_refine_ls_number_parameters     335
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0619P)²+0.9014P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0127(5)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O2 O 0.86525(6) 0.06308(8) 0.41567(5) 0.02468(19) Uani 1 1 d . . . . .
O4 O 0.63934(8) 0.04607(9) 0.55987(5) 0.0373(2) Uani 1 1 d . . . . .
O7 O 0.53237(6) 0.29016(8) 0.37295(5) 0.0248(2) Uani 1 1 d . . . . .
O16 O 0.54065(7) 0.09726(9) 0.06835(5) 0.0326(2) Uani 1 1 d . . . . .
O20 O 0.79126(6) -0.21940(8) 0.52080(5) 0.0272(2) Uani 1 1 d . . . . .
O21 O 0.68121(6) -0.13505(8) 0.42364(5) 0.0269(2) Uani 1 1 d . . . . .
O30 O 0.61768(7) 0.36240(10) 0.53647(6) 0.0413(3) Uani 1 1 d . . . . .
O31 O 0.76947(7) 0.35052(9) 0.52297(5) 0.0316(2) Uani 1 1 d . . . . .
N1 N 0.72843(7) 0.17586(9) 0.41793(5) 0.0195(2) Uani 1 1 d . . . . .
C2 C 0.79699(8) 0.08447(10) 0.44168(6) 0.0190(2) Uani 1 1 d . . . . .
C3 C 0.77612(8) 0.01149(11) 0.50705(6) 0.0208(2) Uani 1 1 d . . . . .
C4 C 0.68488(9) 0.07656(11) 0.51666(6) 0.0238(2) Uani 1 1 d . . . . .
C5 C 0.65921(8) 0.19077(11) 0.46257(6) 0.0213(2) Uani 1 1 d . . . . .
C6 C 0.55325(8) 0.18155(11) 0.41934(7) 0.0250(2) Uani 1 1 d . . . . .
H6A H 0.5420 0.1020 0.3893 0.030 Uiso 1 1 calc R U . . .
H6B H 0.5111 0.1799 0.4539 0.030 Uiso 1 1 calc R U . . .
C8 C 0.43254(8) 0.30392(12) 0.32942(7) 0.0255(3) Uani 1 1 d . . . . .
C9 C 0.36439(10) 0.30074(16) 0.37950(8) 0.0385(3) Uani 1 1 d . . . . .
H9A H 0.2975 0.3101 0.3494 0.046 Uiso 1 1 calc R U . . .
H9B H 0.3714 0.2187 0.4061 0.046 Uiso 1 1 calc R U . . .
H9C H 0.3802 0.3714 0.4153 0.046 Uiso 1 1 calc R U . . .
C10 C 0.43102(11) 0.43545(15) 0.29464(9) 0.0429(4) Uani 1 1 d . . . . .
H10A H 0.3657 0.4537 0.2638 0.052 Uiso 1 1 calc R U . . .
H10B H 0.4493 0.5004 0.3338 0.052 Uiso 1 1 calc R U . . .
H10C H 0.4770 0.4374 0.2638 0.052 Uiso 1 1 calc R U . . .
C11 C 0.40800(11) 0.20060(16) 0.27022(9) 0.0445(4) Uani 1 1 d . . . . .
H11A H 0.3406 0.2108 0.2413 0.053 Uiso 1 1 calc R U . . .
H11B H 0.4511 0.2084 0.2373 0.053 Uiso 1 1 calc R U . . .
H11C H 0.4164 0.1158 0.2938 0.053 Uiso 1 1 calc R U . . .
C12 C 0.73463(8) 0.26534(11) 0.35879(6) 0.0210(2) Uani 1 1 d . . . . .
H12A H 0.8037 0.2786 0.3604 0.025 Uiso 1 1 calc R U . . .
H12B H 0.7077 0.3493 0.3685 0.025 Uiso 1 1 calc R U . . .
C13 C 0.68144(8) 0.22056(10) 0.28170(6) 0.0193(2) Uani 1 1 d . . . . .
C14 C 0.66079(8) 0.09137(11) 0.26482(6) 0.0219(2) Uani 1 1 d . . . . .
H14 H 0.6790 0.0285 0.3028 0.026 Uiso 1 1 calc R U . . .
C15 C 0.61399(9) 0.05378(11) 0.19326(6) 0.0247(2) Uani 1 1 d . . . . .
H15 H 0.6001 -0.0345 0.1826 0.030 Uiso 1 1 calc R U . . .
C16 C 0.58712(8) 0.14486(11) 0.13676(6) 0.0232(2) Uani 1 1 d . . . . .
C17 C 0.60792(8) 0.27388(11) 0.15241(6) 0.0234(2) Uani 1 1 d . . . . .
H17 H 0.5905 0.3366 0.1143 0.028 Uiso 1 1 calc R U . . .
C18 C 0.65467(8) 0.31008(11) 0.22468(6) 0.0220(2) Uani 1 1 d . . . . .
H18 H 0.6686 0.3983 0.2353 0.026 Uiso 1 1 calc R U . . .
C19 C 0.50057(10) 0.18736(13) 0.01075(7) 0.0307(3) Uani 1 1 d . . . . .
H19A H 0.4696 0.1410 -0.0350 0.037 Uiso 1 1 calc R U . . .
H19B H 0.4523 0.2407 0.0256 0.037 Uiso 1 1 calc R U . . .
H19C H 0.5523 0.2422 0.0021 0.037 Uiso 1 1 calc R U . . .
C20 C 0.75256(8) -0.12864(11) 0.48601(6) 0.0204(2) Uani 1 1 d . . . . .
C22 C 0.64948(10) -0.26509(12) 0.39850(7) 0.0300(3) Uani 1 1 d . . . . .
H22A H 0.6244 -0.3100 0.4364 0.036 Uiso 1 1 calc R U . . .
H22B H 0.7043 -0.3152 0.3897 0.036 Uiso 1 1 calc R U . . .
C23 C 0.57132(8) -0.25124(11) 0.32795(6) 0.0229(2) Uani 1 1 d . . . . .
C24 C 0.58567(9) -0.29522(11) 0.26127(7) 0.0254(3) Uani 1 1 d . . . . .
H24 H 0.6457 -0.3335 0.2604 0.030 Uiso 1 1 calc R U . . .
C25 C 0.51295(10) -0.28356(12) 0.19599(7) 0.0298(3) Uani 1 1 d . . . . .
H25 H 0.5230 -0.3145 0.1507 0.036 Uiso 1 1 calc R U . . .
C26 C 0.42572(10) -0.22687(13) 0.19678(7) 0.0331(3) Uani 1 1 d . . . . .
H26 H 0.3759 -0.2184 0.1520 0.040 Uiso 1 1 calc R U . . .
C27 C 0.41125(10) -0.18244(14) 0.26319(8) 0.0357(3) Uani 1 1 d . . . . .
H27 H 0.3515 -0.1431 0.2638 0.043 Uiso 1 1 calc R U . . .
C28 C 0.48327(9) -0.19503(13) 0.32854(7) 0.0299(3) Uani 1 1 d . . . . .
H28 H 0.4726 -0.1653 0.3739 0.036 Uiso 1 1 calc R U . . .
C29 C 0.85970(9) 0.02264(12) 0.57723(6) 0.0291(3) Uani 1 1 d . . . . .
H29A H 0.9172 -0.0201 0.5692 0.035 Uiso 1 1 calc R U . . .
H29B H 0.8742 0.1135 0.5886 0.035 Uiso 1 1 calc R U . . .
H29C H 0.8412 -0.0183 0.6188 0.035 Uiso 1 1 calc R U . . .
C30 C 0.67738(9) 0.31330(11) 0.51065(6) 0.0253(3) Uani 1 1 d . . . . .
C32 C 0.79802(11) 0.46210(14) 0.57039(9) 0.0412(3) Uani 1 1 d . . . . .
H32A H 0.8667 0.4807 0.5756 0.049 Uiso 1 1 calc R U . . .
H32B H 0.7589 0.5363 0.5482 0.049 Uiso 1 1 calc R U . . .
H32C H 0.7878 0.4446 0.6194 0.049 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
O2 C2 1.2184(14) . ?
O4 C4 1.2034(15) . ?
O7 C6 1.4082(14) . ?
O7 C8 1.4543(14) . ?
O16 C16 1.3697(14) . ?
O16 C19 1.4296(15) . ?
O20 C20 1.1974(14) . ?
O21 C20 1.3352(13) . ?
O21 C22 1.4657(14) . ?
O30 C30 1.1982(15) . ?
O31 C30 1.3340(16) . ?
O31 C32 1.4531(15) . ?
N1 C2 1.3554(14) . ?
N1 C5 1.4583(13) . ?
N1 C12 1.4646(13) . ?
C2 C3 1.5310(15) . ?
C3 C4 1.5214(16) . ?
C3 C20 1.5257(15) . ?
C3 C29 1.5308(15) . ?
C4 C5 1.5411(15) . ?
C5 C6 1.5231(16) . ?
C5 C30 1.5425(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C10 1.5132(18) . ?
C8 C9 1.5159(17) . ?
C8 C11 1.5164(19) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.5155(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.3914(15) . ?
C13 C14 1.3955(16) . ?
C14 C15 1.3856(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.3958(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.3905(17) . ?
C17 C18 1.3927(16) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C22 C23 1.4961(16) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.3905(16) . ?
C23 C28 1.3911(17) . ?
C24 C25 1.3862(18) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.388(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.3828(19) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O7 C8 116.29(9) . . ?
C16 O16 C19 117.77(10) . . ?
C20 O21 C22 115.34(9) . . ?
C30 O31 C32 116.46(10) . . ?
C2 N1 C5 115.37(9) . . ?
C2 N1 C12 120.85(9) . . ?
C5 N1 C12 123.09(9) . . ?
O2 C2 N1 125.75(10) . . ?
O2 C2 C3 124.69(10) . . ?
N1 C2 C3 109.56(9) . . ?
C4 C3 C20 108.52(9) . . ?
C4 C3 C29 111.59(9) . . ?
C20 C3 C29 111.33(9) . . ?
C4 C3 C2 102.92(9) . . ?
C20 C3 C2 110.20(9) . . ?
C29 C3 C2 111.94(9) . . ?
O4 C4 C3 126.25(11) . . ?
O4 C4 C5 124.36(11) . . ?
C3 C4 C5 109.39(9) . . ?
N1 C5 C6 114.84(9) . . ?
N1 C5 C4 102.16(8) . . ?
C6 C5 C4 109.46(9) . . ?
N1 C5 C30 112.56(9) . . ?
C6 C5 C30 110.74(9) . . ?
C4 C5 C30 106.36(9) . . ?
O7 C6 C5 107.32(9) . . ?
O7 C6 H6A 110.2 . . ?
C5 C6 H6A 110.2 . . ?
O7 C6 H6B 110.2 . . ?
C5 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
O7 C8 C10 103.37(10) . . ?
O7 C8 C9 110.39(10) . . ?
C10 C8 C9 110.14(11) . . ?
O7 C8 C11 110.17(10) . . ?
C10 C8 C11 110.78(12) . . ?
C9 C8 C11 111.69(12) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 113.96(9) . . ?
N1 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
N1 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C18 C13 C14 118.23(10) . . ?
C18 C13 C12 119.36(10) . . ?
C14 C13 C12 122.37(10) . . ?
C15 C14 C13 120.71(10) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.35(11) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
O16 C16 C17 124.81(10) . . ?
O16 C16 C15 115.46(10) . . ?
C17 C16 C15 119.73(10) . . ?
C16 C17 C18 119.18(10) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C13 C18 C17 121.79(10) . . ?
C13 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
O16 C19 H19A 109.5 . . ?
O16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O20 C20 O21 125.02(10) . . ?
O20 C20 C3 125.11(10) . . ?
O21 C20 C3 109.86(9) . . ?
O21 C22 C23 106.91(9) . . ?
O21 C22 H22A 110.3 . . ?
C23 C22 H22A 110.3 . . ?
O21 C22 H22B 110.3 . . ?
C23 C22 H22B 110.3 . . ?
H22A C22 H22B 108.6 . . ?
C24 C23 C28 119.35(11) . . ?
C24 C23 C22 120.38(11) . . ?
C28 C23 C22 120.27(11) . . ?
C25 C24 C23 120.42(11) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 120.02(11) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 119.72(12) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C28 C27 C26 120.42(12) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C23 120.06(11) . . ?
C27 C28 H28 120.0 . . ?
C23 C28 H28 120.0 . . ?
C3 C29 H29A 109.5 . . ?
C3 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C3 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O30 C30 O31 125.54(12) . . ?
O30 C30 C5 123.84(12) . . ?
O31 C30 C5 110.48(9) . . ?
O31 C32 H32A 109.5 . . ?
O31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
C5 N1 C2 O2 -174.42(10) . . . . ?
C12 N1 C2 O2 -3.68(16) . . . . ?
C5 N1 C2 C3 5.33(12) . . . . ?
C12 N1 C2 C3 176.07(9) . . . . ?
O2 C2 C3 C4 179.57(10) . . . . ?
N1 C2 C3 C4 -0.18(11) . . . . ?
O2 C2 C3 C20 -64.87(13) . . . . ?
N1 C2 C3 C20 115.38(10) . . . . ?
O2 C2 C3 C29 59.61(14) . . . . ?
N1 C2 C3 C29 -120.14(10) . . . . ?
C20 C3 C4 O4 59.39(15) . . . . ?
C29 C3 C4 O4 -63.64(16) . . . . ?
C2 C3 C4 O4 176.16(12) . . . . ?
C20 C3 C4 C5 -121.31(10) . . . . ?
C29 C3 C4 C5 115.66(10) . . . . ?
C2 C3 C4 C5 -4.54(11) . . . . ?
C2 N1 C5 C6 -126.20(10) . . . . ?
C12 N1 C5 C6 63.29(13) . . . . ?
C2 N1 C5 C4 -7.83(12) . . . . ?
C12 N1 C5 C4 -178.33(9) . . . . ?
C2 N1 C5 C30 105.85(11) . . . . ?
C12 N1 C5 C30 -64.66(13) . . . . ?
O4 C4 C5 N1 -173.44(12) . . . . ?
C3 C4 C5 N1 7.24(12) . . . . ?
O4 C4 C5 C6 -51.31(16) . . . . ?
C3 C4 C5 C6 129.37(10) . . . . ?
O4 C4 C5 C30 68.37(15) . . . . ?
C3 C4 C5 C30 -110.94(10) . . . . ?
C8 O7 C6 C5 -176.70(9) . . . . ?
N1 C5 C6 O7 -68.04(12) . . . . ?
C4 C5 C6 O7 177.77(9) . . . . ?
C30 C5 C6 O7 60.82(12) . . . . ?
C6 O7 C8 C10 172.66(11) . . . . ?
C6 O7 C8 C9 54.89(14) . . . . ?
C6 O7 C8 C11 -68.93(14) . . . . ?
C2 N1 C12 C13 92.05(12) . . . . ?
C5 N1 C12 C13 -97.94(12) . . . . ?
N1 C12 C13 C18 159.27(10) . . . . ?
N1 C12 C13 C14 -22.89(15) . . . . ?
C18 C13 C14 C15 -0.63(16) . . . . ?
C12 C13 C14 C15 -178.49(10) . . . . ?
C13 C14 C15 C16 0.29(17) . . . . ?
C19 O16 C16 C17 -7.66(17) . . . . ?
C19 O16 C16 C15 172.16(11) . . . . ?
C14 C15 C16 O16 -179.52(11) . . . . ?
C14 C15 C16 C17 0.32(17) . . . . ?
O16 C16 C17 C18 179.26(11) . . . . ?
C15 C16 C17 C18 -0.56(17) . . . . ?
C14 C13 C18 C17 0.39(16) . . . . ?
C12 C13 C18 C17 178.31(10) . . . . ?
C16 C17 C18 C13 0.21(17) . . . . ?
C22 O21 C20 O20 0.76(17) . . . . ?
C22 O21 C20 C3 -178.20(9) . . . . ?
C4 C3 C20 O20 -120.55(12) . . . . ?
C29 C3 C20 O20 2.63(16) . . . . ?
C2 C3 C20 O20 127.45(12) . . . . ?
C4 C3 C20 O21 58.41(11) . . . . ?
C29 C3 C20 O21 -178.40(9) . . . . ?
C2 C3 C20 O21 -53.58(12) . . . . ?
C20 O21 C22 C23 -179.00(9) . . . . ?
O21 C22 C23 C24 114.19(12) . . . . ?
O21 C22 C23 C28 -66.28(14) . . . . ?
C28 C23 C24 C25 -0.16(17) . . . . ?
C22 C23 C24 C25 179.37(11) . . . . ?
C23 C24 C25 C26 0.56(18) . . . . ?
C24 C25 C26 C27 -0.33(19) . . . . ?
C25 C26 C27 C28 -0.3(2) . . . . ?
C26 C27 C28 C23 0.7(2) . . . . ?
C24 C23 C28 C27 -0.47(19) . . . . ?
C22 C23 C28 C27 180.00(12) . . . . ?
C32 O31 C30 O30 -1.58(19) . . . . ?
C32 O31 C30 C5 -177.43(11) . . . . ?
N1 C5 C30 O30 160.20(12) . . . . ?
C6 C5 C30 O30 30.12(16) . . . . ?
C4 C5 C30 O30 -88.72(14) . . . . ?
N1 C5 C30 O31 -23.87(13) . . . . ?
C6 C5 C30 O31 -153.94(10) . . . . ?
C4 C5 C30 O31 87.22(11) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_25
_database_code_depnum_ccdc_archive 'CCDC 1916076'
loop_
_audit_author_name
_audit_author_address
'ALEXANDRA MARTHA ZOYA Slawin' 'University of St Andrews'
_audit_update_record             
;
2019-05-14 deposited with the CCDC.	2019-09-12 downloaded from the CCDC.
;
_audit_creation_date             2018-03-28
_audit_creation_method           'by CrystalStructure 4.3'


_chemical_formula_sum            'C24 H27 N O5'
_chemical_formula_moiety         'C24 H27 N O5'
_chemical_formula_weight         409.48
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.24701(5)
_cell_length_b                   17.78990(14)
_cell_length_c                   20.26860(16)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2252.52(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21724
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      75.20
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872.00
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.8d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_T_max  0.986

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            26719
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_theta_max         75.563
_diffrn_reflns_theta_min         3.305
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4594
_reflns_number_gt                4503
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_max     0.969
_reflns_Friedel_fraction_full    0.996

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1331
_refine_ls_wR_factor_gt          0.1325
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4594
_refine_ls_number_parameters     271
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0915P)²+0.5780P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.80
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1866 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.00(4)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O2 O 0.2288(3) 0.49171(10) 0.32666(8) 0.0326(4) Uani 1 1 d . . . . .
O4 O 0.7213(3) 0.59883(11) 0.47496(8) 0.0373(4) Uani 1 1 d . . . . .
O7 O 0.5193(3) 0.69155(10) 0.34844(11) 0.0389(4) Uani 1 1 d . . . . .
O18 O 0.3565(4) 0.43756(12) 0.50660(9) 0.0486(6) Uani 1 1 d . . . . .
O19 O 0.6020(3) 0.41572(9) 0.42840(8) 0.0346(4) Uani 1 1 d . . . . .
N1 N 0.5678(3) 0.54095(10) 0.31663(9) 0.0232(4) Uani 1 1 d . . . . .
C2 C 0.3897(4) 0.51910(12) 0.35008(11) 0.0246(4) Uani 1 1 d . . . . .
C3 C 0.4259(4) 0.53250(13) 0.42412(11) 0.0267(5) Uani 1 1 d . . . . .
C4 C 0.6373(4) 0.57366(13) 0.42612(11) 0.0275(5) Uani 1 1 d . . . . .
C5 C 0.7250(3) 0.58208(12) 0.35634(10) 0.0246(4) Uani 1 1 d . . . . .
H5 H 0.8703 0.5590 0.3524 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7309(4) 0.66536(13) 0.33898(12) 0.0300(5) Uani 1 1 d . . . . .
H6A H 0.8317 0.6925 0.3681 0.036 Uiso 1 1 calc R U . . .
H6B H 0.7762 0.6726 0.2926 0.036 Uiso 1 1 calc R U . . .
C8 C 0.4821(5) 0.77125(14) 0.34922(15) 0.0405(6) Uani 1 1 d . . . . .
C9 C 0.2461(6) 0.7805(2) 0.3567(3) 0.0723(12) Uani 1 1 d . . . . .
H9A H 0.2106 0.8342 0.3575 0.087 Uiso 1 1 calc R U . . .
H9B H 0.1731 0.7565 0.3194 0.087 Uiso 1 1 calc R U . . .
H9C H 0.1994 0.7570 0.3980 0.087 Uiso 1 1 calc R U . . .
C10 C 0.5734(9) 0.8113(2) 0.2919(3) 0.0959(18) Uani 1 1 d . . . . .
H10A H 0.5421 0.8651 0.2957 0.115 Uiso 1 1 calc R U . . .
H10B H 0.7287 0.8038 0.2909 0.115 Uiso 1 1 calc R U . . .
H10C H 0.5099 0.7916 0.2512 0.115 Uiso 1 1 calc R U . . .
C11 C 0.5846(8) 0.8012(3) 0.4134(3) 0.0903(16) Uani 1 1 d . . . . .
H11A H 0.5632 0.8557 0.4161 0.108 Uiso 1 1 calc R U . . .
H11B H 0.5173 0.7769 0.4515 0.108 Uiso 1 1 calc R U . . .
H11C H 0.7382 0.7901 0.4132 0.108 Uiso 1 1 calc R U . . .
C12 C 0.5989(4) 0.53152(11) 0.24708(10) 0.0232(4) Uani 1 1 d . . . . .
C13 C 0.7940(4) 0.50485(13) 0.22451(11) 0.0284(5) Uani 1 1 d . . . . .
H13 H 0.9053 0.4933 0.2548 0.034 Uiso 1 1 calc R U . . .
C14 C 0.8254(4) 0.49515(14) 0.15669(12) 0.0334(5) Uani 1 1 d . . . . .
H14 H 0.9590 0.4773 0.1407 0.040 Uiso 1 1 calc R U . . .
C15 C 0.6620(5) 0.51161(15) 0.11284(11) 0.0361(6) Uani 1 1 d . . . . .
H15 H 0.6830 0.5043 0.0669 0.043 Uiso 1 1 calc R U . . .
C16 C 0.4680(5) 0.53867(15) 0.13594(11) 0.0353(5) Uani 1 1 d . . . . .
H16 H 0.3564 0.5500 0.1057 0.042 Uiso 1 1 calc R U . . .
C17 C 0.4357(4) 0.54938(13) 0.20337(11) 0.0293(5) Uani 1 1 d . . . . .
H17 H 0.3035 0.5687 0.2192 0.035 Uiso 1 1 calc R U . . .
C18 C 0.4520(4) 0.45676(14) 0.45872(11) 0.0308(5) Uani 1 1 d . . . . .
C20 C 0.6473(5) 0.34315(15) 0.45899(14) 0.0415(6) Uani 1 1 d . . . . .
H20A H 0.5159 0.3120 0.4601 0.050 Uiso 1 1 calc R U . . .
H20B H 0.6977 0.3505 0.5048 0.050 Uiso 1 1 calc R U . . .
C21 C 0.8162(4) 0.30484(14) 0.41915(11) 0.0318(5) Uani 1 1 d . . . . .
C22 C 0.8023(5) 0.22766(14) 0.40779(13) 0.0376(6) Uani 1 1 d . . . . .
H22 H 0.6801 0.2007 0.4225 0.045 Uiso 1 1 calc R U . . .
C23 C 0.9644(5) 0.19015(14) 0.37531(13) 0.0396(6) Uani 1 1 d . . . . .
H23 H 0.9542 0.1374 0.3686 0.048 Uiso 1 1 calc R U . . .
C24 C 1.1407(5) 0.22856(16) 0.35263(13) 0.0412(6) Uani 1 1 d . . . . .
H24 H 1.2530 0.2026 0.3308 0.049 Uiso 1 1 calc R U . . .
C25 C 1.1529(6) 0.30556(18) 0.36200(18) 0.0535(8) Uani 1 1 d . . . . .
H25 H 1.2726 0.3327 0.3456 0.064 Uiso 1 1 calc R U . . .
C26 C 0.9913(5) 0.34320(16) 0.39515(17) 0.0475(7) Uani 1 1 d . . . . .
H26 H 1.0014 0.3960 0.4014 0.057 Uiso 1 1 calc R U . . .
C27 C 0.2454(4) 0.57706(16) 0.45632(13) 0.0362(5) Uani 1 1 d . . . . .
H27A H 0.1121 0.5482 0.4538 0.043 Uiso 1 1 calc R U . . .
H27B H 0.2809 0.5866 0.5027 0.043 Uiso 1 1 calc R U . . .
H27C H 0.2272 0.6250 0.4332 0.043 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
O2 C2 1.214(3) . ?
O4 C4 1.206(3) . ?
O7 C6 1.415(3) . ?
O7 C8 1.437(3) . ?
O18 C18 1.189(3) . ?
O19 C18 1.337(3) . ?
O19 C20 1.460(3) . ?
N1 C2 1.359(3) . ?
N1 C12 1.433(3) . ?
N1 C5 1.466(3) . ?
C2 C3 1.536(3) . ?
C3 C4 1.511(3) . ?
C3 C27 1.525(3) . ?
C3 C18 1.528(3) . ?
C4 C5 1.524(3) . ?
C5 C6 1.523(3) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C10 1.477(5) . ?
C8 C9 1.491(5) . ?
C8 C11 1.544(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.386(3) . ?
C12 C17 1.388(3) . ?
C13 C14 1.399(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.395(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C20 C21 1.493(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C26 1.378(4) . ?
C21 C22 1.395(4) . ?
C22 C23 1.380(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.375(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O7 C8 118.5(2) . . ?
C18 O19 C20 115.06(18) . . ?
C2 N1 C12 124.62(18) . . ?
C2 N1 C5 114.65(17) . . ?
C12 N1 C5 120.53(18) . . ?
O2 C2 N1 126.7(2) . . ?
O2 C2 C3 124.5(2) . . ?
N1 C2 C3 108.82(18) . . ?
C4 C3 C27 112.52(19) . . ?
C4 C3 C18 108.78(18) . . ?
C27 C3 C18 109.93(19) . . ?
C4 C3 C2 103.30(18) . . ?
C27 C3 C2 112.96(19) . . ?
C18 C3 C2 109.09(18) . . ?
O4 C4 C3 125.6(2) . . ?
O4 C4 C5 124.7(2) . . ?
C3 C4 C5 109.68(18) . . ?
N1 C5 C6 112.03(17) . . ?
N1 C5 C4 102.71(17) . . ?
C6 C5 C4 108.58(18) . . ?
N1 C5 H5 111.1 . . ?
C6 C5 H5 111.1 . . ?
C4 C5 H5 111.1 . . ?
O7 C6 C5 105.45(19) . . ?
O7 C6 H6A 110.7 . . ?
C5 C6 H6A 110.7 . . ?
O7 C6 H6B 110.7 . . ?
C5 C6 H6B 110.7 . . ?
H6A C6 H6B 108.8 . . ?
O7 C8 C10 113.9(3) . . ?
O7 C8 C9 105.7(2) . . ?
C10 C8 C9 114.1(4) . . ?
O7 C8 C11 106.4(3) . . ?
C10 C8 C11 109.6(4) . . ?
C9 C8 C11 106.6(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 120.92(19) . . ?
C13 C12 N1 118.95(19) . . ?
C17 C12 N1 120.1(2) . . ?
C12 C13 C14 119.4(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.1(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 120.3(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 119.2(2) . . ?
C12 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
O18 C18 O19 124.7(2) . . ?
O18 C18 C3 125.1(2) . . ?
O19 C18 C3 110.20(18) . . ?
O19 C20 C21 108.1(2) . . ?
O19 C20 H20A 110.1 . . ?
C21 C20 H20A 110.1 . . ?
O19 C20 H20B 110.1 . . ?
C21 C20 H20B 110.1 . . ?
H20A C20 H20B 108.4 . . ?
C26 C21 C22 118.6(2) . . ?
C26 C21 C20 121.7(2) . . ?
C22 C21 C20 119.6(2) . . ?
C23 C22 C21 120.6(3) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 120.5(2) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 119.3(3) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C26 C25 C24 120.3(3) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C21 C26 C25 120.7(3) . . ?
C21 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C3 C27 H27A 109.5 . . ?
C3 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C3 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
C12 N1 C2 O2 -3.3(3) . . . . ?
C5 N1 C2 O2 171.6(2) . . . . ?
C12 N1 C2 C3 175.07(19) . . . . ?
C5 N1 C2 C3 -10.0(2) . . . . ?
O2 C2 C3 C4 -174.8(2) . . . . ?
N1 C2 C3 C4 6.8(2) . . . . ?
O2 C2 C3 C27 -53.0(3) . . . . ?
N1 C2 C3 C27 128.6(2) . . . . ?
O2 C2 C3 C18 69.6(3) . . . . ?
N1 C2 C3 C18 -108.8(2) . . . . ?
C27 C3 C4 O4 53.6(3) . . . . ?
C18 C3 C4 O4 -68.4(3) . . . . ?
C2 C3 C4 O4 175.8(2) . . . . ?
C27 C3 C4 C5 -123.7(2) . . . . ?
C18 C3 C4 C5 114.2(2) . . . . ?
C2 C3 C4 C5 -1.6(2) . . . . ?
C2 N1 C5 C6 -107.7(2) . . . . ?
C12 N1 C5 C6 67.4(2) . . . . ?
C2 N1 C5 C4 8.6(2) . . . . ?
C12 N1 C5 C4 -176.30(18) . . . . ?
O4 C4 C5 N1 179.0(2) . . . . ?
C3 C4 C5 N1 -3.6(2) . . . . ?
O4 C4 C5 C6 -62.2(3) . . . . ?
C3 C4 C5 C6 115.14(19) . . . . ?
C8 O7 C6 C5 167.3(2) . . . . ?
N1 C5 C6 O7 57.0(2) . . . . ?
C4 C5 C6 O7 -55.8(2) . . . . ?
C6 O7 C8 C10 51.3(4) . . . . ?
C6 O7 C8 C9 177.3(3) . . . . ?
C6 O7 C8 C11 -69.5(3) . . . . ?
C2 N1 C12 C13 -135.3(2) . . . . ?
C5 N1 C12 C13 50.1(3) . . . . ?
C2 N1 C12 C17 45.1(3) . . . . ?
C5 N1 C12 C17 -129.5(2) . . . . ?
C17 C12 C13 C14 -0.7(3) . . . . ?
N1 C12 C13 C14 179.7(2) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C13 C12 C17 C16 1.4(3) . . . . ?
N1 C12 C17 C16 -179.0(2) . . . . ?
C15 C16 C17 C12 -1.0(4) . . . . ?
C20 O19 C18 O18 -0.9(4) . . . . ?
C20 O19 C18 C3 177.5(2) . . . . ?
C4 C3 C18 O18 118.6(3) . . . . ?
C27 C3 C18 O18 -5.0(4) . . . . ?
C2 C3 C18 O18 -129.4(3) . . . . ?
C4 C3 C18 O19 -59.8(2) . . . . ?
C27 C3 C18 O19 176.6(2) . . . . ?
C2 C3 C18 O19 52.2(3) . . . . ?
C18 O19 C20 C21 179.8(2) . . . . ?
O19 C20 C21 C26 42.4(4) . . . . ?
O19 C20 C21 C22 -140.2(2) . . . . ?
C26 C21 C22 C23 2.3(4) . . . . ?
C20 C21 C22 C23 -175.2(3) . . . . ?
C21 C22 C23 C24 -1.1(4) . . . . ?
C22 C23 C24 C25 -0.8(4) . . . . ?
C23 C24 C25 C26 1.4(5) . . . . ?
C22 C21 C26 C25 -1.7(5) . . . . ?
C20 C21 C26 C25 175.8(3) . . . . ?
C24 C25 C26 C21 -0.2(6) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_26
_database_code_depnum_ccdc_archive 'CCDC 1916073'
loop_
_audit_author_name
_audit_author_address
'ALEXANDRA MARTHA ZOYA Slawin' 'University of St Andrews'
_audit_update_record             
;
2019-05-14 deposited with the CCDC.	2019-09-12 downloaded from the CCDC.
;
_audit_creation_date             2017-08-15
_audit_creation_method           'by CrystalStructure 4.2'


_chemical_formula_sum            'C28 H33 N O8'
_chemical_formula_moiety         'C28 H33 N O8'
_chemical_formula_weight         511.57
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   10.3313(2)
_cell_length_b                   10.2519(2)
_cell_length_c                   26.4465(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 98.891(2)
_cell_angle_gamma                90.0000
_cell_volume                     2767.44(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14945
_cell_measurement_theta_min      1.68
_cell_measurement_theta_max      67.72
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088.00
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.8d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_T_max  0.928

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            22931
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_theta_max         68.206
_diffrn_reflns_theta_min         1.691
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             9321
_reflns_number_gt                8699
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_max     0.856
_reflns_Friedel_fraction_full    0.863

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.2038
_refine_ls_wR_factor_gt          0.2011
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         9321
_refine_ls_number_parameters     667
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1400P)²+0.7186P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.003
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 3469 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(8)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O2 O 1.2079(4) 0.4727(4) 0.94922(15) 0.0781(10) Uani 1 1 d . . . . .
O4 O 1.1375(5) 0.5261(6) 0.77061(16) 0.0987(15) Uani 1 1 d . . . . .
O7 O 0.8301(3) 0.6940(4) 0.84224(13) 0.0683(9) Uani 1 1 d . . . . .
O16 O 0.6073(5) 0.4856(6) 1.02493(19) 0.1015(16) Uani 1 1 d . . . . .
O20 O 1.2290(6) 0.2204(5) 0.8422(3) 0.123(2) Uani 1 1 d . . . . .
O21 O 1.0358(4) 0.2945(4) 0.8572(2) 0.0984(15) Uani 1 1 d . . . . .
O30 O 1.0504(6) 0.8396(7) 0.7949(3) 0.136(3) Uani 1 1 d . . . . .
O31 O 1.2115(4) 0.7937(4) 0.85639(16) 0.0736(9) Uani 1 1 d . . . . .
O42 O 0.2474(4) 0.8959(4) 0.45600(13) 0.0725(9) Uani 1 1 d . . . . .
O44 O 0.1918(5) 0.8894(5) 0.27630(14) 0.0870(12) Uani 1 1 d . . . . .
O47 O 0.5392(4) 0.6876(4) 0.34055(15) 0.0749(10) Uani 1 1 d . . . . .
O56 O 0.9128(4) 0.8848(6) 0.52531(19) 0.0980(14) Uani 1 1 d . . . . .
O60 O 0.1463(4) 1.1709(4) 0.3574(2) 0.0967(14) Uani 1 1 d . . . . .
O61 O 0.3505(3) 1.0954(3) 0.37183(14) 0.0640(8) Uani 1 1 d . . . . .
O70 O 0.2719(8) 0.5792(8) 0.2848(3) 0.152(3) Uani 1 1 d . . . . .
O71 O 0.1731(4) 0.5938(4) 0.35222(17) 0.0760(10) Uani 1 1 d . . . . .
N1 N 1.0743(3) 0.6016(4) 0.89332(13) 0.0533(8) Uani 1 1 d . . . . .
N41 N 0.3366(3) 0.7801(4) 0.39639(13) 0.0517(7) Uani 1 1 d . . . . .
C2 C 1.1643(4) 0.5064(4) 0.90619(18) 0.0556(10) Uani 1 1 d . . . . .
C3 C 1.2045(5) 0.4479(5) 0.8576(2) 0.0614(11) Uani 1 1 d . . . . .
C4 C 1.1314(5) 0.5326(5) 0.81572(18) 0.0624(11) Uani 1 1 d . . . . .
C5 C 1.0480(4) 0.6344(5) 0.83928(16) 0.0541(9) Uani 1 1 d . . . . .
C6 C 0.9056(4) 0.6173(5) 0.81463(19) 0.0618(11) Uani 1 1 d . . . . .
H6A H 0.8938 0.6456 0.7784 0.074 Uiso 1 1 calc R U . . .
H6B H 0.8794 0.5246 0.8158 0.074 Uiso 1 1 calc R U . . .
C8 C 0.6939(5) 0.7130(6) 0.8203(2) 0.0691(13) Uani 1 1 d . . . . .
C9 C 0.6305(6) 0.5858(8) 0.8023(3) 0.0966(19) Uani 1 1 d . . . . .
H9A H 0.5387 0.6011 0.7877 0.116 Uiso 1 1 calc R U . . .
H9B H 0.6768 0.5477 0.7761 0.116 Uiso 1 1 calc R U . . .
H9C H 0.6348 0.5255 0.8313 0.116 Uiso 1 1 calc R U . . .
C10 C 0.6301(7) 0.7612(13) 0.8649(4) 0.136(4) Uani 1 1 d . . . . .
H10A H 0.5366 0.7767 0.8533 0.163 Uiso 1 1 calc R U . . .
H10B H 0.6404 0.6953 0.8921 0.163 Uiso 1 1 calc R U . . .
H10C H 0.6719 0.8426 0.8782 0.163 Uiso 1 1 calc R U . . .
C11 C 0.6831(10) 0.8069(13) 0.7775(5) 0.161(5) Uani 1 1 d . . . . .
H11A H 0.5906 0.8188 0.7631 0.193 Uiso 1 1 calc R U . . .
H11B H 0.7206 0.8908 0.7901 0.193 Uiso 1 1 calc R U . . .
H11C H 0.7308 0.7734 0.7510 0.193 Uiso 1 1 calc R U . . .
C12 C 1.0287(5) 0.6813(5) 0.93313(17) 0.0599(10) Uani 1 1 d . . . . .
H12A H 0.9989 0.7667 0.9182 0.072 Uiso 1 1 calc R U . . .
H12B H 1.1036 0.6978 0.9606 0.072 Uiso 1 1 calc R U . . .
C13 C 0.9180(4) 0.6205(5) 0.95689(16) 0.0551(9) Uani 1 1 d . . . . .
C14 C 0.8730(5) 0.4963(5) 0.94687(18) 0.0631(11) Uani 1 1 d . . . . .
H14 H 0.9127 0.4435 0.9240 0.076 Uiso 1 1 calc R U . . .
C15 C 0.7703(5) 0.4450(6) 0.9693(2) 0.0714(13) Uani 1 1 d . . . . .
H15 H 0.7412 0.3579 0.9626 0.086 Uiso 1 1 calc R U . . .
C16 C 0.7120(5) 0.5245(7) 1.0017(2) 0.0730(14) Uani 1 1 d . . . . .
C17 C 0.7564(5) 0.6513(6) 1.0117(2) 0.0728(14) Uani 1 1 d . . . . .
H17 H 0.7159 0.7051 1.0340 0.087 Uiso 1 1 calc R U . . .
C18 C 0.8586(5) 0.6995(6) 0.98962(19) 0.0680(12) Uani 1 1 d . . . . .
H18 H 0.8886 0.7862 0.9966 0.082 Uiso 1 1 calc R U . . .
C19 C 0.5573(7) 0.3586(10) 1.0147(3) 0.106(2) Uani 1 1 d . . . . .
H19A H 0.4838 0.3440 1.0334 0.127 Uiso 1 1 calc R U . . .
H19B H 0.5269 0.3492 0.9779 0.127 Uiso 1 1 calc R U . . .
H19C H 0.6263 0.2946 1.0256 0.127 Uiso 1 1 calc R U . . .
C20 C 1.1614(6) 0.3088(5) 0.8508(3) 0.0757(15) Uani 1 1 d . . . . .
C22 C 0.9860(9) 0.1628(8) 0.8521(6) 0.158(6) Uani 1 1 d . . . . .
H22A H 1.0473 0.1030 0.8733 0.190 Uiso 1 1 calc R U . . .
H22B H 0.9785 0.1345 0.8160 0.190 Uiso 1 1 calc R U . . .
C23 C 0.8531(6) 0.1575(5) 0.8693(3) 0.0767(15) Uani 1 1 d . . . . .
C24 C 0.8412(9) 0.0976(7) 0.9171(3) 0.110(3) Uani 1 1 d . . . . .
H24 H 0.9154 0.0653 0.9393 0.132 Uiso 1 1 calc R U . . .
C25 C 0.7103(11) 0.0888(9) 0.9301(3) 0.108(3) Uani 1 1 d . . . . .
H25 H 0.6958 0.0464 0.9607 0.129 Uiso 1 1 calc R U . . .
C26 C 0.6131(9) 0.1392(10) 0.8995(4) 0.114(3) Uani 1 1 d . . . . .
H26 H 0.5276 0.1347 0.9084 0.137 Uiso 1 1 calc R U . . .
C27 C 0.6295(8) 0.1968(11) 0.8562(4) 0.113(3) Uani 1 1 d . . . . .
H27 H 0.5554 0.2330 0.8352 0.135 Uiso 1 1 calc R U . . .
C28 C 0.7468(8) 0.2060(7) 0.8411(2) 0.0913(19) Uani 1 1 d . . . . .
H28 H 0.7540 0.2480 0.8097 0.110 Uiso 1 1 calc R U . . .
C29 C 1.3534(6) 0.4602(7) 0.8585(3) 0.0842(16) Uani 1 1 d . . . . .
H29A H 1.3792 0.5520 0.8629 0.101 Uiso 1 1 calc R U . . .
H29B H 1.3995 0.4087 0.8869 0.101 Uiso 1 1 calc R U . . .
H29C H 1.3761 0.4278 0.8261 0.101 Uiso 1 1 calc R U . . .
C30 C 1.0999(5) 0.7682(5) 0.82712(19) 0.0643(11) Uani 1 1 d . . . . .
C32 C 1.2757(7) 0.9139(7) 0.8456(4) 0.098(2) Uani 1 1 d . . . . .
H32A H 1.3576 0.9233 0.8696 0.118 Uiso 1 1 calc R U . . .
H32B H 1.2949 0.9117 0.8105 0.118 Uiso 1 1 calc R U . . .
H32C H 1.2180 0.9879 0.8496 0.118 Uiso 1 1 calc R U . . .
C42 C 0.2578(4) 0.8726(4) 0.41180(16) 0.0526(9) Uani 1 1 d . . . . .
C43 C 0.1817(4) 0.9399(4) 0.36520(18) 0.0549(10) Uani 1 1 d . . . . .
C44 C 0.2252(4) 0.8690(5) 0.32094(17) 0.0584(10) Uani 1 1 d . . . . .
C45 C 0.3228(4) 0.7606(4) 0.34123(16) 0.0537(9) Uani 1 1 d . . . . .
C46 C 0.4475(5) 0.7795(5) 0.31857(18) 0.0613(10) Uani 1 1 d . . . . .
H46A H 0.4296 0.7675 0.2810 0.074 Uiso 1 1 calc R U . . .
H46B H 0.4819 0.8688 0.3258 0.074 Uiso 1 1 calc R U . . .
C48 C 0.6558(5) 0.6675(7) 0.3178(2) 0.0767(14) Uani 1 1 d . . . . .
C49 C 0.7117(8) 0.8002(10) 0.3029(4) 0.122(3) Uani 1 1 d . . . . .
H49A H 0.7908 0.7850 0.2875 0.146 Uiso 1 1 calc R U . . .
H49B H 0.6461 0.8449 0.2782 0.146 Uiso 1 1 calc R U . . .
H49C H 0.7336 0.8543 0.3335 0.146 Uiso 1 1 calc R U . . .
C50 C 0.7535(10) 0.6126(16) 0.3609(5) 0.186(8) Uani 1 1 d . . . . .
H50A H 0.8368 0.5958 0.3487 0.223 Uiso 1 1 calc R U . . .
H50B H 0.7676 0.6754 0.3892 0.223 Uiso 1 1 calc R U . . .
H50C H 0.7196 0.5308 0.3730 0.223 Uiso 1 1 calc R U . . .
C51 C 0.6269(12) 0.5824(19) 0.2734(6) 0.218(10) Uani 1 1 d . . . . .
H51A H 0.7065 0.5692 0.2581 0.261 Uiso 1 1 calc R U . . .
H51B H 0.5954 0.4980 0.2840 0.261 Uiso 1 1 calc R U . . .
H51C H 0.5592 0.6226 0.2481 0.261 Uiso 1 1 calc R U . . .
C52 C 0.4167(4) 0.6950(5) 0.43371(17) 0.0581(10) Uani 1 1 d . . . . .
H52A H 0.4326 0.6118 0.4167 0.070 Uiso 1 1 calc R U . . .
H52B H 0.3666 0.6748 0.4617 0.070 Uiso 1 1 calc R U . . .
C53 C 0.5463(4) 0.7527(5) 0.45639(16) 0.0542(9) Uani 1 1 d . . . . .
C54 C 0.5817(5) 0.8816(5) 0.45114(18) 0.0617(11) Uani 1 1 d . . . . .
H54 H 0.5208 0.9387 0.4317 0.074 Uiso 1 1 calc R U . . .
C55 C 0.7026(5) 0.9308(6) 0.4731(2) 0.0675(12) Uani 1 1 d . . . . .
H55 H 0.7241 1.0196 0.4684 0.081 Uiso 1 1 calc R U . . .
C56 C 0.7914(5) 0.8486(6) 0.50192(19) 0.0704(13) Uani 1 1 d . . . . .
C57 C 0.7583(5) 0.7185(7) 0.5076(2) 0.0780(15) Uani 1 1 d . . . . .
H57 H 0.8194 0.6618 0.5272 0.094 Uiso 1 1 calc R U . . .
C58 C 0.6393(5) 0.6706(6) 0.4855(2) 0.0673(12) Uani 1 1 d . . . . .
H58 H 0.6190 0.5813 0.4898 0.081 Uiso 1 1 calc R U . . .
C59 C 0.9503(6) 1.0154(9) 0.5205(3) 0.100(2) Uani 1 1 d . . . . .
H59A H 1.0392 1.0282 0.5390 0.121 Uiso 1 1 calc R U . . .
H59B H 0.9486 1.0363 0.4843 0.121 Uiso 1 1 calc R U . . .
H59C H 0.8894 1.0727 0.5349 0.121 Uiso 1 1 calc R U . . .
C60 C 0.2212(4) 1.0825(5) 0.36430(19) 0.0608(11) Uani 1 1 d . . . . .
C62 C 0.3991(5) 1.2291(5) 0.3739(2) 0.0695(13) Uani 1 1 d . . . . .
H62A H 0.3728 1.2751 0.4036 0.083 Uiso 1 1 calc R U . . .
H62B H 0.3618 1.2765 0.3424 0.083 Uiso 1 1 calc R U . . .
C63 C 0.5474(5) 1.2248(4) 0.37883(19) 0.0573(10) Uani 1 1 d . . . . .
C64 C 0.6228(5) 1.2749(6) 0.42248(19) 0.0677(12) Uani 1 1 d . . . . .
H64 H 0.5815 1.3071 0.4497 0.081 Uiso 1 1 calc R U . . .
C65 C 0.7581(5) 1.2781(6) 0.4266(2) 0.0738(13) Uani 1 1 d . . . . .
H65 H 0.8091 1.3139 0.4563 0.089 Uiso 1 1 calc R U . . .
C66 C 0.8179(6) 1.2304(7) 0.3882(3) 0.0837(16) Uani 1 1 d . . . . .
H66 H 0.9106 1.2345 0.3908 0.100 Uiso 1 1 calc R U . . .
C67 C 0.7431(6) 1.1754(8) 0.3452(3) 0.0885(17) Uani 1 1 d . . . . .
H67 H 0.7849 1.1380 0.3191 0.106 Uiso 1 1 calc R U . . .
C68 C 0.6074(6) 1.1754(7) 0.3405(2) 0.0781(14) Uani 1 1 d . . . . .
H68 H 0.5562 1.1409 0.3106 0.094 Uiso 1 1 calc R U . . .
C69 C 0.0347(5) 0.9284(6) 0.3634(3) 0.0743(14) Uani 1 1 d . . . . .
H69A H 0.0086 0.9753 0.3926 0.089 Uiso 1 1 calc R U . . .
H69B H -0.0102 0.9664 0.3315 0.089 Uiso 1 1 calc R U . . .
H69C H 0.0106 0.8363 0.3652 0.089 Uiso 1 1 calc R U . . .
C70 C 0.2573(5) 0.6306(5) 0.32318(19) 0.0644(11) Uani 1 1 d . . . . .
C72 C 0.0986(7) 0.4770(7) 0.3356(4) 0.100(2) Uani 1 1 d . . . . .
H72A H 0.0383 0.4573 0.3598 0.120 Uiso 1 1 calc R U . . .
H72B H 0.0486 0.4913 0.3015 0.120 Uiso 1 1 calc R U . . .
H72C H 0.1588 0.4035 0.3345 0.120 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
O2 C2 1.208(6) . ?
O4 C4 1.206(6) . ?
O7 C6 1.391(6) . ?
O7 C8 1.450(6) . ?
O16 C16 1.382(7) . ?
O16 C19 1.411(10) . ?
O20 C20 1.188(7) . ?
O21 C20 1.343(7) . ?
O21 C22 1.443(9) . ?
O30 C30 1.179(7) . ?
O31 C30 1.312(6) . ?
O31 C32 1.447(7) . ?
O42 C42 1.214(5) . ?
O44 C44 1.196(6) . ?
O47 C46 1.397(6) . ?
O47 C48 1.443(6) . ?
O56 C56 1.361(7) . ?
O56 C59 1.405(10) . ?
O60 C60 1.187(6) . ?
O61 C60 1.327(6) . ?
O61 C62 1.458(6) . ?
O70 C70 1.173(7) . ?
O71 C70 1.302(6) . ?
O71 C72 1.454(7) . ?
N1 C2 1.356(6) . ?
N1 C5 1.452(6) . ?
N1 C12 1.466(6) . ?
N41 C42 1.353(6) . ?
N41 C45 1.458(5) . ?
N41 C52 1.472(5) . ?
C2 C3 1.531(7) . ?
C3 C20 1.496(7) . ?
C3 C4 1.515(7) . ?
C3 C29 1.540(7) . ?
C4 C5 1.544(6) . ?
C5 C6 1.524(6) . ?
C5 C30 1.525(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C11 1.477(11) . ?
C8 C9 1.504(10) . ?
C8 C10 1.520(9) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.522(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.367(7) . ?
C13 C18 1.395(6) . ?
C14 C15 1.396(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(9) . ?
C17 C18 1.375(8) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C22 C23 1.512(9) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C28 1.325(10) . ?
C23 C24 1.430(11) . ?
C24 C25 1.449(13) . ?
C24 H24 0.9500 . ?
C25 C26 1.296(14) . ?
C25 H25 0.9500 . ?
C26 C27 1.321(14) . ?
C26 H26 0.9500 . ?
C27 C28 1.336(12) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C42 C43 1.521(6) . ?
C43 C44 1.504(7) . ?
C43 C69 1.518(6) . ?
C43 C60 1.519(7) . ?
C44 C45 1.541(6) . ?
C45 C46 1.515(6) . ?
C45 C70 1.537(6) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C48 C51 1.456(12) . ?
C48 C50 1.511(12) . ?
C48 C49 1.552(12) . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 C53 1.501(7) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 C54 1.384(7) . ?
C53 C58 1.412(6) . ?
C54 C55 1.389(7) . ?
C54 H54 0.9500 . ?
C55 C56 1.385(7) . ?
C55 H55 0.9500 . ?
C56 C57 1.391(9) . ?
C57 C58 1.368(9) . ?
C57 H57 0.9500 . ?
C58 H58 0.9500 . ?
C59 H59A 0.9800 . ?
C59 H59B 0.9800 . ?
C59 H59C 0.9800 . ?
C62 C63 1.518(7) . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C63 C68 1.365(7) . ?
C63 C64 1.388(7) . ?
C64 C65 1.385(8) . ?
C64 H64 0.9500 . ?
C65 C66 1.358(9) . ?
C65 H65 0.9500 . ?
C66 C67 1.393(10) . ?
C66 H66 0.9500 . ?
C67 C68 1.389(9) . ?
C67 H67 0.9500 . ?
C68 H68 0.9500 . ?
C69 H69A 0.9800 . ?
C69 H69B 0.9800 . ?
C69 H69C 0.9800 . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C72 H72C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O7 C8 117.1(4) . . ?
C16 O16 C19 118.0(5) . . ?
C20 O21 C22 115.3(5) . . ?
C30 O31 C32 116.2(5) . . ?
C46 O47 C48 118.6(4) . . ?
C56 O56 C59 117.8(5) . . ?
C60 O61 C62 115.6(4) . . ?
C70 O71 C72 115.6(5) . . ?
C2 N1 C5 115.5(4) . . ?
C2 N1 C12 120.3(4) . . ?
C5 N1 C12 123.1(4) . . ?
C42 N41 C45 115.3(3) . . ?
C42 N41 C52 121.0(4) . . ?
C45 N41 C52 123.2(4) . . ?
O2 C2 N1 125.7(4) . . ?
O2 C2 C3 124.7(4) . . ?
N1 C2 C3 109.6(4) . . ?
C20 C3 C4 110.6(5) . . ?
C20 C3 C29 111.0(5) . . ?
C4 C3 C29 110.3(4) . . ?
C20 C3 C2 111.1(4) . . ?
C4 C3 C2 102.7(4) . . ?
C29 C3 C2 110.8(5) . . ?
O4 C4 C3 126.6(5) . . ?
O4 C4 C5 123.6(5) . . ?
C3 C4 C5 109.8(4) . . ?
N1 C5 C6 114.5(4) . . ?
N1 C5 C30 113.4(4) . . ?
C6 C5 C30 111.2(4) . . ?
N1 C5 C4 102.1(4) . . ?
C6 C5 C4 108.1(4) . . ?
C30 C5 C4 106.7(4) . . ?
O7 C6 C5 107.0(4) . . ?
O7 C6 H6A 110.3 . . ?
C5 C6 H6A 110.3 . . ?
O7 C6 H6B 110.3 . . ?
C5 C6 H6B 110.3 . . ?
H6A C6 H6B 108.6 . . ?
O7 C8 C11 110.4(6) . . ?
O7 C8 C9 111.0(5) . . ?
C11 C8 C9 110.1(8) . . ?
O7 C8 C10 104.2(4) . . ?
C11 C8 C10 113.1(9) . . ?
C9 C8 C10 108.0(7) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 114.4(4) . . ?
N1 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
N1 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C18 119.5(5) . . ?
C14 C13 C12 123.8(4) . . ?
C18 C13 C12 116.7(5) . . ?
C13 C14 C15 121.7(4) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C16 C15 C14 118.3(5) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
O16 C16 C15 123.4(6) . . ?
O16 C16 C17 116.3(5) . . ?
C15 C16 C17 120.3(5) . . ?
C18 C17 C16 120.5(5) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C13 119.7(5) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?
O16 C19 H19A 109.5 . . ?
O16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O20 C20 O21 123.3(5) . . ?
O20 C20 C3 125.3(5) . . ?
O21 C20 C3 111.4(4) . . ?
O21 C22 C23 109.4(5) . . ?
O21 C22 H22A 109.8 . . ?
C23 C22 H22A 109.8 . . ?
O21 C22 H22B 109.8 . . ?
C23 C22 H22B 109.8 . . ?
H22A C22 H22B 108.2 . . ?
C28 C23 C24 118.7(6) . . ?
C28 C23 C22 122.1(8) . . ?
C24 C23 C22 119.2(9) . . ?
C23 C24 C25 116.6(7) . . ?
C23 C24 H24 121.7 . . ?
C25 C24 H24 121.7 . . ?
C26 C25 C24 119.3(7) . . ?
C26 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
C25 C26 C27 121.9(8) . . ?
C25 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
C26 C27 C28 122.3(9) . . ?
C26 C27 H27 118.9 . . ?
C28 C27 H27 118.9 . . ?
C23 C28 C27 121.2(7) . . ?
C23 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C3 C29 H29A 109.5 . . ?
C3 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C3 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O30 C30 O31 123.1(5) . . ?
O30 C30 C5 125.7(5) . . ?
O31 C30 C5 111.2(4) . . ?
O31 C32 H32A 109.5 . . ?
O31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O42 C42 N41 125.0(4) . . ?
O42 C42 C43 125.4(4) . . ?
N41 C42 C43 109.5(4) . . ?
C44 C43 C69 110.9(4) . . ?
C44 C43 C60 109.9(4) . . ?
C69 C43 C60 110.1(4) . . ?
C44 C43 C42 103.4(4) . . ?
C69 C43 C42 112.3(4) . . ?
C60 C43 C42 110.1(4) . . ?
O44 C44 C43 127.5(5) . . ?
O44 C44 C45 122.9(5) . . ?
C43 C44 C45 109.6(4) . . ?
N41 C45 C46 114.9(3) . . ?
N41 C45 C44 101.9(3) . . ?
C46 C45 C44 108.7(4) . . ?
N41 C45 C70 113.6(4) . . ?
C46 C45 C70 110.4(4) . . ?
C44 C45 C70 106.5(4) . . ?
O47 C46 C45 108.2(4) . . ?
O47 C46 H46A 110.1 . . ?
C45 C46 H46A 110.1 . . ?
O47 C46 H46B 110.1 . . ?
C45 C46 H46B 110.1 . . ?
H46A C46 H46B 108.4 . . ?
O47 C48 C51 109.9(6) . . ?
O47 C48 C50 104.0(5) . . ?
C51 C48 C50 114.6(12) . . ?
O47 C48 C49 110.4(5) . . ?
C51 C48 C49 111.0(10) . . ?
C50 C48 C49 106.7(9) . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C48 C50 H50A 109.5 . . ?
C48 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C48 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C48 C51 H51A 109.5 . . ?
C48 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C48 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
N41 C52 C53 114.2(4) . . ?
N41 C52 H52A 108.7 . . ?
C53 C52 H52A 108.7 . . ?
N41 C52 H52B 108.7 . . ?
C53 C52 H52B 108.7 . . ?
H52A C52 H52B 107.6 . . ?
C54 C53 C58 117.1(4) . . ?
C54 C53 C52 124.7(4) . . ?
C58 C53 C52 118.2(4) . . ?
C53 C54 C55 122.6(4) . . ?
C53 C54 H54 118.7 . . ?
C55 C54 H54 118.7 . . ?
C56 C55 C54 119.1(5) . . ?
C56 C55 H55 120.5 . . ?
C54 C55 H55 120.5 . . ?
O56 C56 C55 124.7(6) . . ?
O56 C56 C57 115.9(5) . . ?
C55 C56 C57 119.3(5) . . ?
C58 C57 C56 121.2(5) . . ?
C58 C57 H57 119.4 . . ?
C56 C57 H57 119.4 . . ?
C57 C58 C53 120.6(5) . . ?
C57 C58 H58 119.7 . . ?
C53 C58 H58 119.7 . . ?
O56 C59 H59A 109.5 . . ?
O56 C59 H59B 109.5 . . ?
H59A C59 H59B 109.5 . . ?
O56 C59 H59C 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
O60 C60 O61 124.3(5) . . ?
O60 C60 C43 124.6(4) . . ?
O61 C60 C43 111.1(4) . . ?
O61 C62 C63 108.2(4) . . ?
O61 C62 H62A 110.1 . . ?
C63 C62 H62A 110.1 . . ?
O61 C62 H62B 110.1 . . ?
C63 C62 H62B 110.1 . . ?
H62A C62 H62B 108.4 . . ?
C68 C63 C64 119.6(5) . . ?
C68 C63 C62 121.0(5) . . ?
C64 C63 C62 119.4(5) . . ?
C65 C64 C63 120.3(5) . . ?
C65 C64 H64 119.9 . . ?
C63 C64 H64 119.9 . . ?
C66 C65 C64 120.2(5) . . ?
C66 C65 H65 119.9 . . ?
C64 C65 H65 119.9 . . ?
C65 C66 C67 119.8(5) . . ?
C65 C66 H66 120.1 . . ?
C67 C66 H66 120.1 . . ?
C66 C67 C68 119.9(6) . . ?
C66 C67 H67 120.0 . . ?
C68 C67 H67 120.0 . . ?
C63 C68 C67 120.1(6) . . ?
C63 C68 H68 119.9 . . ?
C67 C68 H68 119.9 . . ?
C43 C69 H69A 109.5 . . ?
C43 C69 H69B 109.5 . . ?
H69A C69 H69B 109.5 . . ?
C43 C69 H69C 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
O70 C70 O71 124.5(5) . . ?
O70 C70 C45 123.3(5) . . ?
O71 C70 C45 111.8(4) . . ?
O71 C72 H72A 109.5 . . ?
O71 C72 H72B 109.5 . . ?
H72A C72 H72B 109.5 . . ?
O71 C72 H72C 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 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
C5 N1 C2 O2 173.4(4) . . . . ?
C12 N1 C2 O2 5.0(7) . . . . ?
C5 N1 C2 C3 -6.0(5) . . . . ?
C12 N1 C2 C3 -174.4(4) . . . . ?
O2 C2 C3 C20 66.7(6) . . . . ?
N1 C2 C3 C20 -113.9(5) . . . . ?
O2 C2 C3 C4 -174.9(5) . . . . ?
N1 C2 C3 C4 4.4(5) . . . . ?
O2 C2 C3 C29 -57.1(6) . . . . ?
N1 C2 C3 C29 122.3(5) . . . . ?
C20 C3 C4 O4 -64.7(7) . . . . ?
C29 C3 C4 O4 58.5(8) . . . . ?
C2 C3 C4 O4 176.7(6) . . . . ?
C20 C3 C4 C5 117.0(4) . . . . ?
C29 C3 C4 C5 -119.8(5) . . . . ?
C2 C3 C4 C5 -1.7(5) . . . . ?
C2 N1 C5 C6 121.2(4) . . . . ?
C12 N1 C5 C6 -70.7(5) . . . . ?
C2 N1 C5 C30 -109.8(4) . . . . ?
C12 N1 C5 C30 58.3(5) . . . . ?
C2 N1 C5 C4 4.6(5) . . . . ?
C12 N1 C5 C4 172.7(4) . . . . ?
O4 C4 C5 N1 -179.8(5) . . . . ?
C3 C4 C5 N1 -1.4(5) . . . . ?
O4 C4 C5 C6 59.0(7) . . . . ?
C3 C4 C5 C6 -122.5(4) . . . . ?
O4 C4 C5 C30 -60.6(6) . . . . ?
C3 C4 C5 C30 117.8(4) . . . . ?
C8 O7 C6 C5 168.7(4) . . . . ?
N1 C5 C6 O7 57.0(5) . . . . ?
C30 C5 C6 O7 -73.1(5) . . . . ?
C4 C5 C6 O7 170.1(4) . . . . ?
C6 O7 C8 C11 -75.4(9) . . . . ?
C6 O7 C8 C9 47.0(7) . . . . ?
C6 O7 C8 C10 162.9(7) . . . . ?
C2 N1 C12 C13 -84.3(5) . . . . ?
C5 N1 C12 C13 108.1(5) . . . . ?
N1 C12 C13 C14 7.1(7) . . . . ?
N1 C12 C13 C18 -171.2(4) . . . . ?
C18 C13 C14 C15 -1.3(8) . . . . ?
C12 C13 C14 C15 -179.5(5) . . . . ?
C13 C14 C15 C16 1.3(9) . . . . ?
C19 O16 C16 C15 -0.4(10) . . . . ?
C19 O16 C16 C17 178.4(7) . . . . ?
C14 C15 C16 O16 178.1(6) . . . . ?
C14 C15 C16 C17 -0.7(9) . . . . ?
O16 C16 C17 C18 -178.8(5) . . . . ?
C15 C16 C17 C18 0.0(9) . . . . ?
C16 C17 C18 C13 0.1(8) . . . . ?
C14 C13 C18 C17 0.5(8) . . . . ?
C12 C13 C18 C17 178.9(5) . . . . ?
C22 O21 C20 O20 -1.0(13) . . . . ?
C22 O21 C20 C3 -179.1(9) . . . . ?
C4 C3 C20 O20 116.0(8) . . . . ?
C29 C3 C20 O20 -6.9(10) . . . . ?
C2 C3 C20 O20 -130.6(8) . . . . ?
C4 C3 C20 O21 -65.9(6) . . . . ?
C29 C3 C20 O21 171.3(5) . . . . ?
C2 C3 C20 O21 47.5(7) . . . . ?
C20 O21 C22 C23 170.2(8) . . . . ?
O21 C22 C23 C28 73.9(12) . . . . ?
O21 C22 C23 C24 -106.6(10) . . . . ?
C28 C23 C24 C25 3.0(9) . . . . ?
C22 C23 C24 C25 -176.5(6) . . . . ?
C23 C24 C25 C26 -2.9(11) . . . . ?
C24 C25 C26 C27 1.2(13) . . . . ?
C25 C26 C27 C28 0.5(15) . . . . ?
C24 C23 C28 C27 -1.6(11) . . . . ?
C22 C23 C28 C27 177.9(7) . . . . ?
C26 C27 C28 C23 -0.2(14) . . . . ?
C32 O31 C30 O30 -2.7(9) . . . . ?
C32 O31 C30 C5 175.3(5) . . . . ?
N1 C5 C30 O30 -145.9(7) . . . . ?
C6 C5 C30 O30 -15.2(8) . . . . ?
C4 C5 C30 O30 102.5(8) . . . . ?
N1 C5 C30 O31 36.1(6) . . . . ?
C6 C5 C30 O31 166.9(4) . . . . ?
C4 C5 C30 O31 -75.5(5) . . . . ?
C45 N41 C42 O42 173.9(4) . . . . ?
C52 N41 C42 O42 1.5(7) . . . . ?
C45 N41 C42 C43 -4.5(5) . . . . ?
C52 N41 C42 C43 -176.9(4) . . . . ?
O42 C42 C43 C44 -176.4(4) . . . . ?
N41 C42 C43 C44 1.9(5) . . . . ?
O42 C42 C43 C69 -56.8(6) . . . . ?
N41 C42 C43 C69 121.5(4) . . . . ?
O42 C42 C43 C60 66.2(6) . . . . ?
N41 C42 C43 C60 -115.4(4) . . . . ?
C69 C43 C44 O44 60.2(7) . . . . ?
C60 C43 C44 O44 -61.7(6) . . . . ?
C42 C43 C44 O44 -179.2(5) . . . . ?
C69 C43 C44 C45 -119.5(4) . . . . ?
C60 C43 C44 C45 118.5(4) . . . . ?
C42 C43 C44 C45 1.0(5) . . . . ?
C42 N41 C45 C46 122.2(4) . . . . ?
C52 N41 C45 C46 -65.5(6) . . . . ?
C42 N41 C45 C44 4.8(5) . . . . ?
C52 N41 C45 C44 177.1(4) . . . . ?
C42 N41 C45 C70 -109.3(4) . . . . ?
C52 N41 C45 C70 62.9(5) . . . . ?
O44 C44 C45 N41 176.9(5) . . . . ?
C43 C44 C45 N41 -3.3(5) . . . . ?
O44 C44 C45 C46 55.2(6) . . . . ?
C43 C44 C45 C46 -125.1(4) . . . . ?
O44 C44 C45 C70 -63.8(6) . . . . ?
C43 C44 C45 C70 116.0(4) . . . . ?
C48 O47 C46 C45 167.3(5) . . . . ?
N41 C45 C46 O47 61.6(5) . . . . ?
C44 C45 C46 O47 175.0(4) . . . . ?
C70 C45 C46 O47 -68.5(5) . . . . ?
C46 O47 C48 C51 -80.5(12) . . . . ?
C46 O47 C48 C50 156.4(9) . . . . ?
C46 O47 C48 C49 42.3(8) . . . . ?
C42 N41 C52 C53 -85.1(5) . . . . ?
C45 N41 C52 C53 103.1(5) . . . . ?
N41 C52 C53 C54 11.3(7) . . . . ?
N41 C52 C53 C58 -169.1(4) . . . . ?
C58 C53 C54 C55 0.0(7) . . . . ?
C52 C53 C54 C55 179.6(5) . . . . ?
C53 C54 C55 C56 -0.7(8) . . . . ?
C59 O56 C56 C55 0.9(9) . . . . ?
C59 O56 C56 C57 179.9(6) . . . . ?
C54 C55 C56 O56 179.9(5) . . . . ?
C54 C55 C56 C57 0.9(8) . . . . ?
O56 C56 C57 C58 -179.6(5) . . . . ?
C55 C56 C57 C58 -0.4(9) . . . . ?
C56 C57 C58 C53 -0.2(9) . . . . ?
C54 C53 C58 C57 0.5(8) . . . . ?
C52 C53 C58 C57 -179.2(5) . . . . ?
C62 O61 C60 O60 3.1(8) . . . . ?
C62 O61 C60 C43 -177.4(4) . . . . ?
C44 C43 C60 O60 114.6(6) . . . . ?
C69 C43 C60 O60 -7.8(8) . . . . ?
C42 C43 C60 O60 -132.2(6) . . . . ?
C44 C43 C60 O61 -64.9(5) . . . . ?
C69 C43 C60 O61 172.7(4) . . . . ?
C42 C43 C60 O61 48.4(5) . . . . ?
C60 O61 C62 C63 -176.0(4) . . . . ?
O61 C62 C63 C68 64.9(7) . . . . ?
O61 C62 C63 C64 -116.7(5) . . . . ?
C68 C63 C64 C65 1.8(8) . . . . ?
C62 C63 C64 C65 -176.6(5) . . . . ?
C63 C64 C65 C66 -1.1(9) . . . . ?
C64 C65 C66 C67 -1.4(10) . . . . ?
C65 C66 C67 C68 3.2(11) . . . . ?
C64 C63 C68 C67 -0.1(9) . . . . ?
C62 C63 C68 C67 178.3(6) . . . . ?
C66 C67 C68 C63 -2.4(11) . . . . ?
C72 O71 C70 O70 3.0(10) . . . . ?
C72 O71 C70 C45 175.3(5) . . . . ?
N41 C45 C70 O70 -156.3(7) . . . . ?
C46 C45 C70 O70 -25.6(9) . . . . ?
C44 C45 C70 O70 92.3(8) . . . . ?
N41 C45 C70 O71 31.2(6) . . . . ?
C46 C45 C70 O71 162.0(4) . . . . ?
C44 C45 C70 O71 -80.2(5) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_23a
_database_code_depnum_ccdc_archive 'CCDC 1916075'
loop_
_audit_author_name
_audit_author_address
'ALEXANDRA MARTHA ZOYA Slawin' 'University of St Andrews'
_audit_update_record             
;
2019-05-14 deposited with the CCDC.	2019-09-12 downloaded from the CCDC.
;
_audit_creation_date             2018-05-30
_audit_creation_method           'by CrystalStructure 4.3'


_chemical_formula_sum            'C12 H19 N O5'
_chemical_formula_moiety         'C12 H19 N O5'
_chemical_formula_weight         257.29
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.41466(6)
_cell_length_b                   22.42870(13)
_cell_length_c                   11.38440(9)
_cell_angle_alpha                90.0000
_cell_angle_beta                 107.7070(8)
_cell_angle_gamma                90.0000
_cell_volume                     2046.79(3)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    19190
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      75.18
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             828.00
_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.8d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_T_max  0.849

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            22771
_diffrn_reflns_av_unetI/netI     0.0077
_diffrn_reflns_av_R_equivalents  0.0113
_diffrn_reflns_theta_max         75.367
_diffrn_reflns_theta_min         4.076
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             7799
_reflns_number_gt                7791
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_max     0.857
_reflns_Friedel_fraction_full    0.916

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0749
_refine_ls_wR_factor_gt          0.0749
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         7799
_refine_ls_number_parameters     499
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0526P)²+0.2935P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 3514 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(5)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O2 O 0.46497(15) 0.49690(5) 0.46308(10) 0.0226(2) Uani 1 1 d . . . . .
O4 O 0.53645(15) 0.50921(6) 0.88966(11) 0.0230(2) Uani 1 1 d . . . . .
O7 O 0.82212(13) 0.43121(5) 0.80982(10) 0.0203(2) Uani 1 1 d . . . . .
O12 O 0.36375(18) 0.61963(6) 0.59016(15) 0.0375(3) Uani 1 1 d . . . . .
O13 O 0.23794(15) 0.55055(6) 0.67040(13) 0.0331(3) Uani 1 1 d . . . . .
O22 O 0.35294(17) 0.52831(6) 0.15687(13) 0.0321(3) Uani 1 1 d . . . . .
O24 O 0.23148(17) 0.73369(6) 0.15681(13) 0.0325(3) Uani 1 1 d . . . . .
O27 O 0.60605(14) 0.68703(5) 0.32883(11) 0.0236(2) Uani 1 1 d . . . . .
O32 O 0.04040(18) 0.61556(7) -0.08756(12) 0.0350(3) Uani 1 1 d . . . . .
O33 O -0.00436(15) 0.61022(6) 0.09652(11) 0.0266(3) Uani 1 1 d . . . . .
O42 O 0.48915(15) 0.33438(5) 0.44527(11) 0.0240(2) Uani 1 1 d . . . . .
O44 O 0.5468(2) 0.32745(6) 0.04500(13) 0.0369(3) Uani 1 1 d . . . . .
O47 O 0.81194(14) 0.40992(5) 0.25991(11) 0.0238(2) Uani 1 1 d . . . . .
O52 O 0.3783(2) 0.21010(7) 0.17852(17) 0.0462(4) Uani 1 1 d . . . . .
O53 O 0.22959(16) 0.29227(6) 0.18720(13) 0.0314(3) Uani 1 1 d . . . . .
N1 N 0.50058(16) 0.42927(6) 0.61912(11) 0.0181(3) Uani 1 1 d D . . . .
N21 N 0.35994(18) 0.59820(6) 0.30466(13) 0.0212(3) Uani 1 1 d D . . . .
N41 N 0.47868(16) 0.40255(6) 0.29318(12) 0.0184(3) Uani 1 1 d D . . . .
C2 C 0.48998(18) 0.48415(7) 0.57236(14) 0.0169(3) Uani 1 1 d . . . . .
C3 C 0.51483(18) 0.53054(7) 0.67500(13) 0.0165(3) Uani 1 1 d . . . . .
C4 C 0.52613(17) 0.49161(7) 0.78777(14) 0.0167(3) Uani 1 1 d . . . . .
C5 C 0.52735(18) 0.42598(7) 0.75170(13) 0.0176(3) Uani 1 1 d . . . . .
H5 H 0.4311 0.4050 0.7677 0.021 Uiso 1 1 calc R U . . .
C6 C 0.68964(19) 0.39528(7) 0.82333(15) 0.0198(3) Uani 1 1 d . . . . .
H6A H 0.6969 0.3917 0.9115 0.024 Uiso 1 1 calc R U . . .
H6B H 0.6952 0.3548 0.7900 0.024 Uiso 1 1 calc R U . . .
C8 C 0.98902(19) 0.41439(8) 0.88499(14) 0.0203(3) Uani 1 1 d . . . . .
C9 C 1.1017(2) 0.45784(9) 0.84581(18) 0.0301(4) Uani 1 1 d . . . . .
H9A H 1.2183 0.4497 0.8924 0.036 Uiso 1 1 calc R U . . .
H9B H 1.0863 0.4532 0.7575 0.036 Uiso 1 1 calc R U . . .
H9C H 1.0732 0.4987 0.8623 0.036 Uiso 1 1 calc R U . . .
C10 C 1.0274(2) 0.35085(9) 0.8570(2) 0.0342(4) Uani 1 1 d . . . . .
H10A H 1.1401 0.3402 0.9083 0.041 Uiso 1 1 calc R U . . .
H10B H 0.9463 0.3237 0.8748 0.041 Uiso 1 1 calc R U . . .
H10C H 1.0205 0.3476 0.7697 0.041 Uiso 1 1 calc R U . . .
C11 C 1.0069(2) 0.42290(10) 1.02102(16) 0.0314(4) Uani 1 1 d . . . . .
H11A H 1.1197 0.4114 1.0707 0.038 Uiso 1 1 calc R U . . .
H11B H 0.9875 0.4648 1.0365 0.038 Uiso 1 1 calc R U . . .
H11C H 0.9251 0.3979 1.0434 0.038 Uiso 1 1 calc R U . . .
C12 C 0.3662(2) 0.57299(7) 0.64117(14) 0.0187(3) Uani 1 1 d . . . . .
C14 C 0.0925(3) 0.58917(11) 0.6422(2) 0.0400(5) Uani 1 1 d . . . . .
H14A H 0.0034 0.5694 0.6665 0.048 Uiso 1 1 calc R U . . .
H14B H 0.1221 0.6267 0.6877 0.048 Uiso 1 1 calc R U . . .
H14C H 0.0538 0.5974 0.5535 0.048 Uiso 1 1 calc R U . . .
C15 C 0.6772(2) 0.56514(8) 0.68978(16) 0.0232(3) Uani 1 1 d . . . . .
H15A H 0.7717 0.5374 0.7115 0.028 Uiso 1 1 calc R U . . .
H15B H 0.6713 0.5852 0.6120 0.028 Uiso 1 1 calc R U . . .
H15C H 0.6923 0.5949 0.7552 0.028 Uiso 1 1 calc R U . . .
C22 C 0.33292(19) 0.57908(7) 0.18845(15) 0.0208(3) Uani 1 1 d . . . . .
C23 C 0.2692(2) 0.63130(7) 0.09966(15) 0.0208(3) Uani 1 1 d . . . . .
C24 C 0.27015(19) 0.68324(7) 0.18698(15) 0.0212(3) Uani 1 1 d . . . . .
C25 C 0.3311(2) 0.66102(7) 0.32008(15) 0.0206(3) Uani 1 1 d . . . . .
H25 H 0.2412 0.6660 0.3600 0.025 Uiso 1 1 calc R U . . .
C26 C 0.4861(2) 0.69503(8) 0.39236(15) 0.0233(3) Uani 1 1 d . . . . .
H26A H 0.4602 0.7379 0.3966 0.028 Uiso 1 1 calc R U . . .
H26B H 0.5291 0.6793 0.4774 0.028 Uiso 1 1 calc R U . . .
C28 C 0.7475(2) 0.72692(8) 0.36372(19) 0.0274(4) Uani 1 1 d . . . . .
C29 C 0.6911(2) 0.78994(9) 0.3202(2) 0.0329(4) Uani 1 1 d . . . . .
H29A H 0.7873 0.8169 0.3440 0.039 Uiso 1 1 calc R U . . .
H29B H 0.6425 0.7901 0.2303 0.039 Uiso 1 1 calc R U . . .
H29C H 0.6074 0.8033 0.3584 0.039 Uiso 1 1 calc R U . . .
C30 C 0.8310(3) 0.72517(10) 0.5026(2) 0.0405(5) Uani 1 1 d . . . . .
H30A H 0.9265 0.7524 0.5246 0.049 Uiso 1 1 calc R U . . .
H30B H 0.7508 0.7374 0.5449 0.049 Uiso 1 1 calc R U . . .
H30C H 0.8695 0.6845 0.5276 0.049 Uiso 1 1 calc R U . . .
C31 C 0.8622(3) 0.70274(10) 0.2941(3) 0.0455(6) Uani 1 1 d . . . . .
H31A H 0.9629 0.7274 0.3124 0.055 Uiso 1 1 calc R U . . .
H31B H 0.8931 0.6616 0.3199 0.055 Uiso 1 1 calc R U . . .
H31C H 0.8042 0.7037 0.2053 0.055 Uiso 1 1 calc R U . . .
C32 C 0.0906(2) 0.61813(7) 0.02253(15) 0.0228(3) Uani 1 1 d . . . . .
C34 C -0.1779(2) 0.59559(9) 0.03486(19) 0.0331(4) Uani 1 1 d . . . . .
H34A H -0.2369 0.5907 0.0964 0.040 Uiso 1 1 calc R U . . .
H34B H -0.2299 0.6278 -0.0220 0.040 Uiso 1 1 calc R U . . .
H34C H -0.1841 0.5584 -0.0114 0.040 Uiso 1 1 calc R U . . .
C35 C 0.3809(3) 0.64348(10) 0.01869(19) 0.0341(4) Uani 1 1 d . . . . .
H35A H 0.4947 0.6518 0.0711 0.041 Uiso 1 1 calc R U . . .
H35B H 0.3816 0.6085 -0.0327 0.041 Uiso 1 1 calc R U . . .
H35C H 0.3380 0.6780 -0.0343 0.041 Uiso 1 1 calc R U . . .
C42 C 0.49475(19) 0.34779(7) 0.34145(14) 0.0186(3) Uani 1 1 d . . . . .
C43 C 0.5218(2) 0.30291(7) 0.24786(15) 0.0204(3) Uani 1 1 d . . . . .
C44 C 0.5297(2) 0.34401(7) 0.14090(15) 0.0217(3) Uani 1 1 d . . . . .
C45 C 0.51390(19) 0.40871(7) 0.17637(13) 0.0178(3) Uani 1 1 d . . . . .
H45 H 0.4175 0.4281 0.1140 0.021 Uiso 1 1 calc R U . . .
C46 C 0.67358(19) 0.44422(7) 0.18980(14) 0.0192(3) Uani 1 1 d . . . . .
H46A H 0.6847 0.4529 0.1074 0.023 Uiso 1 1 calc R U . . .
H46B H 0.6695 0.4826 0.2319 0.023 Uiso 1 1 calc R U . . .
C48 C 0.9362(2) 0.43925(9) 0.36078(16) 0.0267(4) Uani 1 1 d . . . . .
C49 C 1.0013(2) 0.49605(9) 0.31940(18) 0.0319(4) Uani 1 1 d . . . . .
H49A H 1.0844 0.5144 0.3899 0.038 Uiso 1 1 calc R U . . .
H49B H 1.0528 0.4866 0.2552 0.038 Uiso 1 1 calc R U . . .
H49C H 0.9086 0.5239 0.2864 0.038 Uiso 1 1 calc R U . . .
C50 C 0.8644(3) 0.45157(15) 0.46568(19) 0.0528(7) Uani 1 1 d . . . . .
H50A H 0.9488 0.4713 0.5333 0.063 Uiso 1 1 calc R U . . .
H50B H 0.7665 0.4775 0.4363 0.063 Uiso 1 1 calc R U . . .
H50C H 0.8316 0.4139 0.4952 0.063 Uiso 1 1 calc R U . . .
C51 C 1.0757(3) 0.39351(12) 0.3978(3) 0.0571(7) Uani 1 1 d . . . . .
H51A H 1.1673 0.4091 0.4664 0.069 Uiso 1 1 calc R U . . .
H51B H 1.0334 0.3566 0.4235 0.069 Uiso 1 1 calc R U . . .
H51C H 1.1163 0.3853 0.3274 0.069 Uiso 1 1 calc R U . . .
C52 C 0.3707(2) 0.26171(8) 0.20135(16) 0.0253(3) Uani 1 1 d . . . . .
C54 C 0.0767(3) 0.25785(11) 0.1442(2) 0.0425(5) Uani 1 1 d . . . . .
H54A H -0.0192 0.2840 0.1368 0.051 Uiso 1 1 calc R U . . .
H54B H 0.0680 0.2404 0.0636 0.051 Uiso 1 1 calc R U . . .
H54C H 0.0780 0.2259 0.2033 0.051 Uiso 1 1 calc R U . . .
C55 C 0.6818(2) 0.26671(8) 0.29848(18) 0.0296(4) Uani 1 1 d . . . . .
H55A H 0.7770 0.2939 0.3277 0.036 Uiso 1 1 calc R U . . .
H55B H 0.6733 0.2418 0.3671 0.036 Uiso 1 1 calc R U . . .
H55C H 0.6979 0.2412 0.2331 0.036 Uiso 1 1 calc R U . . .
H1 H 0.498(3) 0.3944(7) 0.5680(17) 0.025(5) Uiso 1 1 d D . . . .
H21 H 0.398(3) 0.5700(10) 0.3726(17) 0.041(7) Uiso 1 1 d D . . . .
H41 H 0.463(3) 0.4360(7) 0.3430(17) 0.025(5) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
O2 C2 1.231(2) . ?
O4 C4 1.203(2) . ?
O7 C6 1.4213(19) . ?
O7 C8 1.4547(18) . ?
O12 C12 1.194(2) . ?
O13 C12 1.322(2) . ?
O13 C14 1.453(2) . ?
O22 C22 1.221(2) . ?
O24 C24 1.198(2) . ?
O27 C26 1.4204(19) . ?
O27 C28 1.445(2) . ?
O32 C32 1.196(2) . ?
O33 C32 1.338(2) . ?
O33 C34 1.452(2) . ?
O42 C42 1.234(2) . ?
O44 C44 1.203(2) . ?
O47 C46 1.4210(19) . ?
O47 C48 1.454(2) . ?
O52 C52 1.192(2) . ?
O53 C52 1.338(2) . ?
O53 C54 1.452(2) . ?
N1 C2 1.333(2) . ?
N1 C5 1.4587(19) . ?
N1 H1 0.972(7) . ?
N21 C22 1.343(2) . ?
N21 C25 1.449(2) . ?
N21 H21 0.974(7) . ?
N41 C42 1.335(2) . ?
N41 C45 1.4543(19) . ?
N41 H41 0.973(7) . ?
C2 C3 1.531(2) . ?
C3 C12 1.525(2) . ?
C3 C4 1.532(2) . ?
C3 C15 1.536(2) . ?
C4 C5 1.529(2) . ?
C5 C6 1.525(2) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C10 1.516(2) . ?
C8 C9 1.518(2) . ?
C8 C11 1.522(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C22 C23 1.533(2) . ?
C23 C32 1.521(2) . ?
C23 C35 1.528(2) . ?
C23 C24 1.530(2) . ?
C24 C25 1.528(2) . ?
C25 C26 1.519(2) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C28 C31 1.523(3) . ?
C28 C30 1.523(3) . ?
C28 C29 1.525(3) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C42 C43 1.532(2) . ?
C43 C55 1.527(2) . ?
C43 C52 1.530(2) . ?
C43 C44 1.545(2) . ?
C44 C45 1.523(2) . ?
C45 C46 1.529(2) . ?
C45 H45 1.0000 . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C48 C49 1.517(3) . ?
C48 C51 1.519(3) . ?
C48 C50 1.519(3) . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O7 C8 115.97(12) . . ?
C12 O13 C14 114.51(14) . . ?
C26 O27 C28 115.80(12) . . ?
C32 O33 C34 115.54(14) . . ?
C46 O47 C48 117.92(13) . . ?
C52 O53 C54 115.56(16) . . ?
C2 N1 C5 115.49(12) . . ?
C2 N1 H1 121.2(13) . . ?
C5 N1 H1 123.2(13) . . ?
C22 N21 C25 116.45(13) . . ?
C22 N21 H21 119.4(16) . . ?
C25 N21 H21 124.1(16) . . ?
C42 N41 C45 116.13(13) . . ?
C42 N41 H41 119.0(13) . . ?
C45 N41 H41 124.1(13) . . ?
O2 C2 N1 126.02(14) . . ?
O2 C2 C3 123.74(14) . . ?
N1 C2 C3 110.23(13) . . ?
C12 C3 C2 108.69(12) . . ?
C12 C3 C4 113.86(12) . . ?
C2 C3 C4 102.22(13) . . ?
C12 C3 C15 110.26(13) . . ?
C2 C3 C15 109.73(12) . . ?
C4 C3 C15 111.71(12) . . ?
O4 C4 C5 124.78(14) . . ?
O4 C4 C3 126.09(15) . . ?
C5 C4 C3 109.12(12) . . ?
N1 C5 C6 114.04(13) . . ?
N1 C5 C4 102.57(12) . . ?
C6 C5 C4 111.65(12) . . ?
N1 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
C4 C5 H5 109.4 . . ?
O7 C6 C5 106.88(12) . . ?
O7 C6 H6A 110.3 . . ?
C5 C6 H6A 110.3 . . ?
O7 C6 H6B 110.3 . . ?
C5 C6 H6B 110.3 . . ?
H6A C6 H6B 108.6 . . ?
O7 C8 C10 110.44(14) . . ?
O7 C8 C9 103.77(13) . . ?
C10 C8 C9 110.47(15) . . ?
O7 C8 C11 110.20(13) . . ?
C10 C8 C11 111.74(16) . . ?
C9 C8 C11 109.93(15) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O12 C12 O13 124.19(15) . . ?
O12 C12 C3 124.14(14) . . ?
O13 C12 C3 111.62(13) . . ?
O13 C14 H14A 109.5 . . ?
O13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C15 H15A 109.5 . . ?
C3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O22 C22 N21 126.21(16) . . ?
O22 C22 C23 124.76(15) . . ?
N21 C22 C23 109.03(14) . . ?
C32 C23 C35 111.56(14) . . ?
C32 C23 C24 109.39(13) . . ?
C35 C23 C24 111.91(14) . . ?
C32 C23 C22 108.56(13) . . ?
C35 C23 C22 112.23(14) . . ?
C24 C23 C22 102.80(13) . . ?
O24 C24 C25 124.90(15) . . ?
O24 C24 C23 125.84(16) . . ?
C25 C24 C23 109.26(13) . . ?
N21 C25 C26 113.95(13) . . ?
N21 C25 C24 102.41(13) . . ?
C26 C25 C24 110.33(13) . . ?
N21 C25 H25 110.0 . . ?
C26 C25 H25 110.0 . . ?
C24 C25 H25 110.0 . . ?
O27 C26 C25 106.67(13) . . ?
O27 C26 H26A 110.4 . . ?
C25 C26 H26A 110.4 . . ?
O27 C26 H26B 110.4 . . ?
C25 C26 H26B 110.4 . . ?
H26A C26 H26B 108.6 . . ?
O27 C28 C31 103.64(15) . . ?
O27 C28 C30 110.55(16) . . ?
C31 C28 C30 111.44(18) . . ?
O27 C28 C29 109.64(14) . . ?
C31 C28 C29 110.18(17) . . ?
C30 C28 C29 111.15(16) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O32 C32 O33 124.40(16) . . ?
O32 C32 C23 125.91(16) . . ?
O33 C32 C23 109.68(13) . . ?
O33 C34 H34A 109.5 . . ?
O33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C23 C35 H35A 109.5 . . ?
C23 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C23 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O42 C42 N41 126.13(15) . . ?
O42 C42 C43 124.24(15) . . ?
N41 C42 C43 109.63(13) . . ?
C55 C43 C52 110.73(14) . . ?
C55 C43 C42 112.78(14) . . ?
C52 C43 C42 110.73(13) . . ?
C55 C43 C44 111.72(14) . . ?
C52 C43 C44 108.56(13) . . ?
C42 C43 C44 101.96(13) . . ?
O44 C44 C45 125.41(15) . . ?
O44 C44 C43 125.24(15) . . ?
C45 C44 C43 109.35(13) . . ?
N41 C45 C44 102.15(12) . . ?
N41 C45 C46 112.04(12) . . ?
C44 C45 C46 112.19(13) . . ?
N41 C45 H45 110.1 . . ?
C44 C45 H45 110.1 . . ?
C46 C45 H45 110.1 . . ?
O47 C46 C45 108.60(12) . . ?
O47 C46 H46A 110.0 . . ?
C45 C46 H46A 110.0 . . ?
O47 C46 H46B 110.0 . . ?
C45 C46 H46B 110.0 . . ?
H46A C46 H46B 108.4 . . ?
O47 C48 C49 112.04(14) . . ?
O47 C48 C51 102.88(17) . . ?
C49 C48 C51 109.37(17) . . ?
O47 C48 C50 109.94(14) . . ?
C49 C48 C50 111.03(19) . . ?
C51 C48 C50 111.3(2) . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C48 C50 H50A 109.5 . . ?
C48 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C48 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C48 C51 H51A 109.5 . . ?
C48 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C48 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
O52 C52 O53 125.15(17) . . ?
O52 C52 C43 124.59(18) . . ?
O53 C52 C43 110.23(14) . . ?
O53 C54 H54A 109.5 . . ?
O53 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
O53 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C43 C55 H55A 109.5 . . ?
C43 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C43 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 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
C5 N1 C2 O2 -178.70(14) . . . . ?
C5 N1 C2 C3 1.72(17) . . . . ?
O2 C2 C3 C12 54.88(19) . . . . ?
N1 C2 C3 C12 -125.52(14) . . . . ?
O2 C2 C3 C4 175.56(14) . . . . ?
N1 C2 C3 C4 -4.84(15) . . . . ?
O2 C2 C3 C15 -65.77(19) . . . . ?
N1 C2 C3 C15 113.83(14) . . . . ?
C12 C3 C4 O4 -58.5(2) . . . . ?
C2 C3 C4 O4 -175.48(14) . . . . ?
C15 C3 C4 O4 67.26(19) . . . . ?
C12 C3 C4 C5 123.16(13) . . . . ?
C2 C3 C4 C5 6.14(15) . . . . ?
C15 C3 C4 C5 -111.12(14) . . . . ?
C2 N1 C5 C6 -118.64(15) . . . . ?
C2 N1 C5 C4 2.26(16) . . . . ?
O4 C4 C5 N1 176.30(14) . . . . ?
C3 C4 C5 N1 -5.29(15) . . . . ?
O4 C4 C5 C6 -61.17(19) . . . . ?
C3 C4 C5 C6 117.23(13) . . . . ?
C8 O7 C6 C5 171.88(12) . . . . ?
N1 C5 C6 O7 64.26(16) . . . . ?
C4 C5 C6 O7 -51.44(16) . . . . ?
C6 O7 C8 C10 58.59(18) . . . . ?
C6 O7 C8 C9 177.00(14) . . . . ?
C6 O7 C8 C11 -65.35(18) . . . . ?
C14 O13 C12 O12 -3.6(3) . . . . ?
C14 O13 C12 C3 179.15(16) . . . . ?
C2 C3 C12 O12 -94.86(19) . . . . ?
C4 C3 C12 O12 151.94(16) . . . . ?
C15 C3 C12 O12 25.5(2) . . . . ?
C2 C3 C12 O13 82.36(16) . . . . ?
C4 C3 C12 O13 -30.84(19) . . . . ?
C15 C3 C12 O13 -157.32(14) . . . . ?
C25 N21 C22 O22 178.64(16) . . . . ?
C25 N21 C22 C23 -2.33(19) . . . . ?
O22 C22 C23 C32 64.8(2) . . . . ?
N21 C22 C23 C32 -114.28(15) . . . . ?
O22 C22 C23 C35 -59.0(2) . . . . ?
N21 C22 C23 C35 121.95(16) . . . . ?
O22 C22 C23 C24 -179.42(16) . . . . ?
N21 C22 C23 C24 1.53(17) . . . . ?
C32 C23 C24 O24 -66.0(2) . . . . ?
C35 C23 C24 O24 58.1(2) . . . . ?
C22 C23 C24 O24 178.78(16) . . . . ?
C32 C23 C24 C25 114.87(14) . . . . ?
C35 C23 C24 C25 -120.98(15) . . . . ?
C22 C23 C24 C25 -0.35(17) . . . . ?
C22 N21 C25 C26 -117.15(16) . . . . ?
C22 N21 C25 C24 1.99(18) . . . . ?
O24 C24 C25 N21 -179.96(16) . . . . ?
C23 C24 C25 N21 -0.83(16) . . . . ?
O24 C24 C25 C26 -58.3(2) . . . . ?
C23 C24 C25 C26 120.83(14) . . . . ?
C28 O27 C26 C25 165.48(14) . . . . ?
N21 C25 C26 O27 57.39(18) . . . . ?
C24 C25 C26 O27 -57.16(17) . . . . ?
C26 O27 C28 C31 172.88(17) . . . . ?
C26 O27 C28 C30 53.37(19) . . . . ?
C26 O27 C28 C29 -69.51(19) . . . . ?
C34 O33 C32 O32 2.2(3) . . . . ?
C34 O33 C32 C23 -178.34(14) . . . . ?
C35 C23 C32 O32 2.0(2) . . . . ?
C24 C23 C32 O32 126.39(19) . . . . ?
C22 C23 C32 O32 -122.14(19) . . . . ?
C35 C23 C32 O33 -177.41(15) . . . . ?
C24 C23 C32 O33 -53.05(17) . . . . ?
C22 C23 C32 O33 58.42(17) . . . . ?
C45 N41 C42 O42 171.31(14) . . . . ?
C45 N41 C42 C43 -8.67(18) . . . . ?
O42 C42 C43 C55 -56.3(2) . . . . ?
N41 C42 C43 C55 123.66(15) . . . . ?
O42 C42 C43 C52 68.4(2) . . . . ?
N41 C42 C43 C52 -111.63(15) . . . . ?
O42 C42 C43 C44 -176.27(15) . . . . ?
N41 C42 C43 C44 3.71(17) . . . . ?
C55 C43 C44 O44 60.8(2) . . . . ?
C52 C43 C44 O44 -61.6(2) . . . . ?
C42 C43 C44 O44 -178.52(17) . . . . ?
C55 C43 C44 C45 -118.78(15) . . . . ?
C52 C43 C44 C45 118.83(14) . . . . ?
C42 C43 C44 C45 1.91(16) . . . . ?
C42 N41 C45 C44 9.38(17) . . . . ?
C42 N41 C45 C46 -110.89(15) . . . . ?
O44 C44 C45 N41 174.19(17) . . . . ?
C43 C44 C45 N41 -6.24(16) . . . . ?
O44 C44 C45 C46 -65.6(2) . . . . ?
C43 C44 C45 C46 113.92(14) . . . . ?
C48 O47 C46 C45 -132.34(14) . . . . ?
N41 C45 C46 O47 68.30(16) . . . . ?
C44 C45 C46 O47 -45.94(17) . . . . ?
C46 O47 C48 C49 -52.97(19) . . . . ?
C46 O47 C48 C51 -170.33(17) . . . . ?
C46 O47 C48 C50 71.0(2) . . . . ?
C54 O53 C52 O52 2.1(3) . . . . ?
C54 O53 C52 C43 -179.51(15) . . . . ?
C55 C43 C52 O52 -17.5(3) . . . . ?
C42 C43 C52 O52 -143.34(19) . . . . ?
C44 C43 C52 O52 105.5(2) . . . . ?
C55 C43 C52 O53 164.09(14) . . . . ?
C42 C43 C52 O53 38.22(18) . . . . ?
C44 C43 C52 O53 -72.92(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O42 . . . 2.8879(18) 0.972(17) 1.925(18) 170.6(16) no
N21 H21 O2 . . . 2.8681(17) 0.97(2) 1.93(2) 161.5(18) no
N41 H41 O2 . . . 2.8928(18) 0.973(18) 1.929(18) 170.3(16) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


