# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1478434'
_audit_update_record             
;
2016-05-06 deposited with the CCDC.
2018-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H N O'
_chemical_formula_weight         43.03

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

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   6.9872(5)
_cell_length_b                   15.5151(10)
_cell_length_c                   19.4250(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.467(2)
_cell_angle_gamma                90.00
_cell_volume                     2082.9(2)
_cell_formula_units_Z            42
_cell_measurement_temperature    136(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             924
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      136(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21119
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         25.07
_reflns_number_total             7187
_reflns_number_gt                6000
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0636P)²+0.4991P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(12)
_refine_ls_number_reflns         7187
_refine_ls_number_parameters     487
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1098
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3621(3) 0.73678(13) 0.05136(11) 0.0390(5) Uani 1 1 d . . .
N3 N -0.1109(3) 0.68474(14) 0.09637(11) 0.0247(5) Uani 1 1 d . . .
O4 O 0.2989(3) 0.63364(13) -0.04407(11) 0.0351(5) Uani 1 1 d . . .
C4 C 0.0147(4) 0.62515(17) 0.01057(14) 0.0231(6) Uani 1 1 d . . .
O6 O 0.0674(3) 0.54099(13) -0.08526(10) 0.0362(5) Uani 1 1 d . . .
N4 N -0.1624(3) 0.58804(15) 0.01187(11) 0.0262(5) Uani 1 1 d . . .
O2 O 0.1985(4) 0.80413(14) 0.12572(11) 0.0486(6) Uani 1 1 d . . .
C17 C 0.0514(4) 0.68593(17) 0.06338(13) 0.0220(6) Uani 1 1 d . . .
C27 C 0.1288(4) 0.59689(18) -0.04367(14) 0.0269(6) Uani 1 1 d . . .
C28 C -0.2330(4) 0.62546(18) 0.06356(14) 0.0276(6) Uani 1 1 d . . .
H28A H -0.3559 0.6122 0.0763 0.033 Uiso 1 1 calc R . .
C46 C -0.1518(4) 0.7321(2) 0.15814(15) 0.0343(7) Uani 1 1 d . . .
H46A H -0.2810 0.7167 0.1680 0.051 Uiso 1 1 calc R . .
H46B H -0.1464 0.7942 0.1494 0.051 Uiso 1 1 calc R . .
H46C H -0.0552 0.7170 0.1981 0.051 Uiso 1 1 calc R . .
C47 C 0.2144(4) 0.74710(18) 0.08236(15) 0.0290(7) Uani 1 1 d . . .
C6 C 0.1187(4) 0.51129(17) 0.24942(13) 0.0221(6) Uani 1 1 d . . .
C8 C 0.2329(4) 0.64664(17) 0.30238(14) 0.0260(6) Uani 1 1 d . . .
H8A H 0.3274 0.6911 0.3077 0.031 Uiso 1 1 calc R . .
C10 C -0.0391(4) 0.51885(18) 0.28605(14) 0.0262(6) Uani 1 1 d . . .
H10A H -0.1356 0.4753 0.2810 0.031 Uiso 1 1 calc R . .
C11 C 0.2564(4) 0.57721(17) 0.25773(14) 0.0227(6) Uani 1 1 d . . .
C12 C -0.0582(4) 0.40372(17) 0.16479(15) 0.0257(6) Uani 1 1 d . . .
H12A H -0.1424 0.3833 0.1982 0.031 Uiso 1 1 calc R . .
H12B H -0.1205 0.4549 0.1407 0.031 Uiso 1 1 calc R . .
C18 C 0.0877(4) 0.36102(18) 0.05942(14) 0.0265(6) Uani 1 1 d . . .
H18A H 0.0292 0.4114 0.0330 0.032 Uiso 1 1 calc R . .
H18B H 0.0961 0.3137 0.0258 0.032 Uiso 1 1 calc R . .
C20 C 0.2739(4) 0.45264(16) 0.15120(13) 0.0220(6) Uani 1 1 d . . .
H20A H 0.2100 0.5030 0.1251 0.026 Uiso 1 1 calc R . .
C21 C -0.0435(4) 0.33307(18) 0.11122(15) 0.0293(7) Uani 1 1 d . . .
H21A H 0.0086 0.2799 0.1353 0.035 Uiso 1 1 calc R . .
H21B H -0.1740 0.3200 0.0861 0.035 Uiso 1 1 calc R . .
N1 N 0.3762(3) 0.39158(15) -0.03127(12) 0.0290(5) Uani 1 1 d . . .
H1A H 0.4452 0.4218 -0.0586 0.043 Uiso 1 1 d R . .
H1B H 0.4179 0.3366 -0.0284 0.043 Uiso 1 1 d R . .
H1C H 0.2502 0.3928 -0.0496 0.043 Uiso 1 1 d R . .
C25 C 0.2143(4) 0.35818(18) 0.25723(15) 0.0279(6) Uani 1 1 d . . .
H25A H 0.3397 0.3752 0.2831 0.042 Uiso 1 1 calc R . .
H25B H 0.2294 0.3049 0.2315 0.042 Uiso 1 1 calc R . .
H25C H 0.1218 0.3487 0.2898 0.042 Uiso 1 1 calc R . .
C29 C 0.4068(4) 0.30328(18) 0.11884(15) 0.0280(6) Uani 1 1 d . . .
H29A H 0.3413 0.2732 0.1531 0.042 Uiso 1 1 calc R . .
H29B H 0.5377 0.3194 0.1403 0.042 Uiso 1 1 calc R . .
H29C H 0.4144 0.2652 0.0791 0.042 Uiso 1 1 calc R . .
C30 C 0.0551(4) 0.72826(18) 0.38665(14) 0.0305(7) Uani 1 1 d . . .
H30A H 0.1762 0.7635 0.3908 0.037 Uiso 1 1 calc R . .
C31 C 0.4285(4) 0.57676(17) 0.21966(15) 0.0257(6) Uani 1 1 d . . .
H31A H 0.5447 0.5939 0.2523 0.031 Uiso 1 1 calc R . .
H31B H 0.4083 0.6201 0.1819 0.031 Uiso 1 1 calc R . .
C32 C 0.4004(4) 0.42914(17) 0.03869(13) 0.0239(6) Uani 1 1 d . . .
H32A H 0.4788 0.4786 0.0500 0.029 Uiso 1 1 calc R . .
C33 C 0.2924(4) 0.38476(16) 0.09387(14) 0.0218(6) Uani 1 1 d . . .
C34 C 0.0782(4) 0.65280(17) 0.33878(14) 0.0269(6) Uani 1 1 d . . .
C36 C 0.4649(4) 0.48905(17) 0.18839(14) 0.0231(6) Uani 1 1 d . . .
H36A H 0.5211 0.4491 0.2257 0.028 Uiso 1 1 calc R . .
H36B H 0.5581 0.4953 0.1549 0.028 Uiso 1 1 calc R . .
C37 C -0.0577(4) 0.58808(19) 0.32934(14) 0.0287(6) Uani 1 1 d . . .
H37A H -0.1670 0.5910 0.3531 0.034 Uiso 1 1 calc R . .
C38 C 0.0292(6) 0.6986(2) 0.45957(16) 0.0475(9) Uani 1 1 d . . .
H38A H 0.0129 0.7490 0.4886 0.071 Uiso 1 1 calc R . .
H38B H 0.1437 0.6661 0.4802 0.071 Uiso 1 1 calc R . .
H38C H -0.0855 0.6617 0.4568 0.071 Uiso 1 1 calc R . .
C44 C 0.1385(4) 0.43054(17) 0.20540(13) 0.0221(6) Uani 1 1 d . . .
C51 C -0.1130(5) 0.7857(2) 0.35568(18) 0.0457(8) Uani 1 1 d . . .
H51A H -0.0933 0.8045 0.3091 0.069 Uiso 1 1 calc R . .
H51B H -0.1194 0.8362 0.3855 0.069 Uiso 1 1 calc R . .
H51C H -0.2343 0.7533 0.3525 0.069 Uiso 1 1 calc R . .
C13 C 0.7012(4) 0.31269(18) 0.38067(14) 0.0286(6) Uani 1 1 d . . .
H13A H 0.7878 0.3502 0.3620 0.034 Uiso 1 1 calc R . .
N2 N 0.3384(3) -0.02604(14) 0.09536(11) 0.0252(5) Uani 1 1 d . . .
H2A H 0.3216 -0.0022 0.0526 0.038 Uiso 1 1 d R . .
H2B H 0.4277 -0.0681 0.0973 0.038 Uiso 1 1 d R . .
H2C H 0.2256 -0.0484 0.1041 0.038 Uiso 1 1 d R . .
C15 C 0.5332(4) 0.17528(17) 0.37652(13) 0.0256(6) Uani 1 1 d . . .
C16 C 0.5147(4) 0.08825(17) 0.26822(13) 0.0212(6) Uani 1 1 d . . .
H16A H 0.4279 0.1366 0.2494 0.025 Uiso 1 1 calc R . .
C19 C 0.7184(4) 0.11765(18) 0.25862(14) 0.0270(6) Uani 1 1 d . . .
H19A H 0.8152 0.0772 0.2829 0.032 Uiso 1 1 calc R . .
H19B H 0.7309 0.1172 0.2085 0.032 Uiso 1 1 calc R . .
C22 C 0.6633(4) 0.23118(18) 0.35050(14) 0.0264(6) Uani 1 1 d . . .
C24 C 0.4068(4) 0.04084(17) 0.14782(13) 0.0257(6) Uani 1 1 d . . .
H24A H 0.3103 0.0880 0.1441 0.031 Uiso 1 1 calc R . .
H24B H 0.5294 0.0654 0.1366 0.031 Uiso 1 1 calc R . .
C26 C 0.2435(4) -0.02166(18) 0.24125(14) 0.0279(6) Uani 1 1 d . . .
H26A H 0.1429 0.0203 0.2220 0.034 Uiso 1 1 calc R . .
H26B H 0.2103 -0.0778 0.2183 0.034 Uiso 1 1 calc R . .
C35 C 0.4974(4) 0.08479(17) 0.34747(13) 0.0237(6) Uani 1 1 d . . .
C39 C 0.6160(5) 0.34028(18) 0.43701(15) 0.0331(7) Uani 1 1 d . . .
C40 C 0.4869(5) 0.2851(2) 0.46249(16) 0.0407(8) Uani 1 1 d . . .
H40A H 0.4240 0.3031 0.5002 0.049 Uiso 1 1 calc R . .
C41 C 0.4406(4) 0.00849(16) 0.22307(13) 0.0217(6) Uani 1 1 d . . .
C42 C 0.4483(5) 0.20386(19) 0.43361(15) 0.0360(7) Uani 1 1 d . . .
H42A H 0.3622 0.1667 0.4530 0.043 Uiso 1 1 calc R . .
C43 C 0.7577(4) 0.20865(18) 0.28791(14) 0.0275(6) Uani 1 1 d . . .
H43A H 0.8993 0.2159 0.3005 0.033 Uiso 1 1 calc R . .
H43B H 0.7136 0.2506 0.2505 0.033 Uiso 1 1 calc R . .
C45 C 0.2940(4) 0.05357(18) 0.35609(15) 0.0300(7) Uani 1 1 d . . .
H45A H 0.2869 0.0465 0.4063 0.036 Uiso 1 1 calc R . .
H45B H 0.1987 0.0982 0.3377 0.036 Uiso 1 1 calc R . .
C48 C 0.5849(4) -0.06623(19) 0.22887(15) 0.0334(7) Uani 1 1 d . . .
H48A H 0.5305 -0.1138 0.1990 0.050 Uiso 1 1 calc R . .
H48B H 0.6108 -0.0859 0.2773 0.050 Uiso 1 1 calc R . .
H48C H 0.7058 -0.0468 0.2140 0.050 Uiso 1 1 calc R . .
C49 C 0.6497(5) 0.02654(19) 0.39093(15) 0.0360(7) Uani 1 1 d . . .
H49A H 0.6295 0.0275 0.4398 0.054 Uiso 1 1 calc R . .
H49B H 0.7798 0.0479 0.3872 0.054 Uiso 1 1 calc R . .
H49C H 0.6363 -0.0326 0.3733 0.054 Uiso 1 1 calc R . .
C50 C 0.2392(5) -0.03130(19) 0.31895(15) 0.0355(7) Uani 1 1 d . . .
H50A H 0.3311 -0.0769 0.3381 0.043 Uiso 1 1 calc R . .
H50B H 0.1079 -0.0487 0.3269 0.043 Uiso 1 1 calc R . .
C99 C 0.5366(5) 0.49636(19) 0.42234(17) 0.0423(8) Uani 1 1 d . . .
H99A H 0.5626 0.5538 0.4425 0.063 Uiso 1 1 calc R . .
H99B H 0.3986 0.4831 0.4198 0.063 Uiso 1 1 calc R . .
H99C H 0.5725 0.4950 0.3754 0.063 Uiso 1 1 calc R . .
C98 C 0.6543(5) 0.43006(19) 0.46761(15) 0.0369(7) Uani 1 1 d . . .
H98A H 0.6071 0.4305 0.5138 0.044 Uiso 1 1 calc R . .
C97 C 0.8664(5) 0.45229(19) 0.48067(16) 0.0412(8) Uani 1 1 d . . .
H97A H 0.8829 0.5106 0.5001 0.062 Uiso 1 1 calc R . .
H97B H 0.9195 0.4498 0.4367 0.062 Uiso 1 1 calc R . .
H97C H 0.9348 0.4110 0.5137 0.062 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C47 1.279(4) . ?
N3 C28 1.349(3) . ?
N3 C17 1.383(3) . ?
N3 C46 1.470(4) . ?
O4 C27 1.319(3) . ?
C4 N4 1.368(3) . ?
C4 C17 1.389(4) . ?
C4 C27 1.478(4) . ?
O6 C27 1.219(3) . ?
N4 C28 1.317(3) . ?
O2 C47 1.238(4) . ?
C17 C47 1.487(4) . ?
C28 H28A 0.9500 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C6 C11 1.397(4) . ?
C6 C10 1.402(4) . ?
C6 C44 1.534(4) . ?
C8 C34 1.379(4) . ?
C8 C11 1.408(4) . ?
C8 H8A 0.9500 . ?
C10 C37 1.382(4) . ?
C10 H10A 0.9500 . ?
C11 C31 1.502(4) . ?
C12 C21 1.525(4) . ?
C12 C44 1.538(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C18 C21 1.521(4) . ?
C18 C33 1.532(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C20 C36 1.529(4) . ?
C20 C33 1.552(4) . ?
C20 C44 1.554(4) . ?
C20 H20A 1.0000 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
N1 C32 1.465(3) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N1 H1C 0.9000 . ?
C25 C44 1.548(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C29 C33 1.536(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C34 1.518(4) . ?
C30 C38 1.525(4) . ?
C30 C51 1.526(4) . ?
C30 H30A 1.0000 . ?
C31 C36 1.527(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.559(4) . ?
C32 H32A 0.9500 . ?
C34 C37 1.376(4) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 H37A 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C13 C39 1.388(4) . ?
C13 C22 1.403(4) . ?
C13 H13A 0.9500 . ?
N2 C24 1.483(3) . ?
N2 H2A 0.9001 . ?
N2 H2B 0.9000 . ?
N2 H2C 0.9001 . ?
C15 C22 1.404(4) . ?
C15 C42 1.404(4) . ?
C15 C35 1.520(4) . ?
C16 C19 1.532(4) . ?
C16 C41 1.560(3) . ?
C16 C35 1.563(4) . ?
C16 H16A 1.0000 . ?
C19 C43 1.532(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C22 C43 1.507(4) . ?
C24 C41 1.531(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C26 C50 1.521(4) . ?
C26 C41 1.544(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C35 C45 1.534(4) . ?
C35 C49 1.548(4) . ?
C39 C40 1.387(4) . ?
C39 C98 1.523(4) . ?
C40 C42 1.390(4) . ?
C40 H40A 0.9500 . ?
C41 C48 1.530(4) . ?
C42 H42A 0.9500 . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C45 C50 1.523(4) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C99 C98 1.515(4) . ?
C99 H99A 0.9800 . ?
C99 H99B 0.9800 . ?
C99 H99C 0.9800 . ?
C98 C97 1.506(4) . ?
C98 H98A 1.0000 . ?
C97 H97A 0.9800 . ?
C97 H97B 0.9800 . ?
C97 H97C 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
C28 N3 C17 107.2(2) . . ?
C28 N3 C46 122.8(2) . . ?
C17 N3 C46 130.0(2) . . ?
N4 C4 C17 109.9(2) . . ?
N4 C4 C27 118.2(2) . . ?
C17 C4 C27 131.9(2) . . ?
C28 N4 C4 105.7(2) . . ?
N3 C17 C4 105.0(2) . . ?
N3 C17 C47 123.0(2) . . ?
C4 C17 C47 131.9(2) . . ?
O6 C27 O4 122.2(3) . . ?
O6 C27 C4 120.6(2) . . ?
O4 C27 C4 117.2(2) . . ?
N4 C28 N3 112.3(2) . . ?
N4 C28 H28A 123.9 . . ?
N3 C28 H28A 123.9 . . ?
N3 C46 H46A 109.5 . . ?
N3 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
N3 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
O2 C47 O1 124.7(3) . . ?
O2 C47 C17 118.9(3) . . ?
O1 C47 C17 116.4(3) . . ?
C11 C6 C10 117.3(2) . . ?
C11 C6 C44 123.0(2) . . ?
C10 C6 C44 119.5(2) . . ?
C34 C8 C11 122.7(3) . . ?
C34 C8 H8A 118.7 . . ?
C11 C8 H8A 118.7 . . ?
C37 C10 C6 121.7(3) . . ?
C37 C10 H10A 119.2 . . ?
C6 C10 H10A 119.2 . . ?
C6 C11 C8 119.4(2) . . ?
C6 C11 C31 121.8(2) . . ?
C8 C11 C31 118.8(2) . . ?
C21 C12 C44 113.6(2) . . ?
C21 C12 H12A 108.9 . . ?
C44 C12 H12A 108.9 . . ?
C21 C12 H12B 108.9 . . ?
C44 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C21 C18 C33 113.2(2) . . ?
C21 C18 H18A 108.9 . . ?
C33 C18 H18A 108.9 . . ?
C21 C18 H18B 108.9 . . ?
C33 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C36 C20 C33 115.5(2) . . ?
C36 C20 C44 109.7(2) . . ?
C33 C20 C44 117.4(2) . . ?
C36 C20 H20A 104.2 . . ?
C33 C20 H20A 104.2 . . ?
C44 C20 H20A 104.2 . . ?
C18 C21 C12 110.7(2) . . ?
C18 C21 H21A 109.5 . . ?
C12 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C12 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C32 N1 H1A 110.0 . . ?
C32 N1 H1B 109.1 . . ?
H1A N1 H1B 109.5 . . ?
C32 N1 H1C 109.3 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C44 C25 H25A 109.5 . . ?
C44 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C44 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C33 C29 H29A 109.5 . . ?
C33 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C33 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C34 C30 C38 112.0(2) . . ?
C34 C30 C51 110.7(2) . . ?
C38 C30 C51 110.6(3) . . ?
C34 C30 H30A 107.8 . . ?
C38 C30 H30A 107.8 . . ?
C51 C30 H30A 107.8 . . ?
C11 C31 C36 113.1(2) . . ?
C11 C31 H31A 109.0 . . ?
C36 C31 H31A 109.0 . . ?
C11 C31 H31B 109.0 . . ?
C36 C31 H31B 109.0 . . ?
H31A C31 H31B 107.8 . . ?
N1 C32 C33 117.4(2) . . ?
N1 C32 H32A 121.3 . . ?
C33 C32 H32A 121.3 . . ?
C18 C33 C29 110.4(2) . . ?
C18 C33 C20 107.8(2) . . ?
C29 C33 C20 115.2(2) . . ?
C18 C33 C32 108.7(2) . . ?
C29 C33 C32 107.4(2) . . ?
C20 C33 C32 107.1(2) . . ?
C37 C34 C8 117.3(2) . . ?
C37 C34 C30 120.7(3) . . ?
C8 C34 C30 122.0(3) . . ?
C31 C36 C20 109.4(2) . . ?
C31 C36 H36A 109.8 . . ?
C20 C36 H36A 109.8 . . ?
C31 C36 H36B 109.8 . . ?
C20 C36 H36B 109.8 . . ?
H36A C36 H36B 108.2 . . ?
C34 C37 C10 121.5(3) . . ?
C34 C37 H37A 119.2 . . ?
C10 C37 H37A 119.2 . . ?
C30 C38 H38A 109.5 . . ?
C30 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C30 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C6 C44 C12 111.1(2) . . ?
C6 C44 C25 106.3(2) . . ?
C12 C44 C25 109.4(2) . . ?
C6 C44 C20 108.1(2) . . ?
C12 C44 C20 107.4(2) . . ?
C25 C44 C20 114.6(2) . . ?
C30 C51 H51A 109.5 . . ?
C30 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C30 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C39 C13 C22 122.1(3) . . ?
C39 C13 H13A 118.9 . . ?
C22 C13 H13A 118.9 . . ?
C24 N2 H2A 109.3 . . ?
C24 N2 H2B 109.1 . . ?
H2A N2 H2B 109.5 . . ?
C24 N2 H2C 110.0 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C22 C15 C42 117.4(3) . . ?
C22 C15 C35 121.1(2) . . ?
C42 C15 C35 121.3(2) . . ?
C19 C16 C41 113.9(2) . . ?
C19 C16 C35 109.8(2) . . ?
C41 C16 C35 117.3(2) . . ?
C19 C16 H16A 104.8 . . ?
C41 C16 H16A 104.8 . . ?
C35 C16 H16A 104.8 . . ?
C43 C19 C16 110.4(2) . . ?
C43 C19 H19A 109.6 . . ?
C16 C19 H19A 109.6 . . ?
C43 C19 H19B 109.6 . . ?
C16 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C13 C22 C15 119.9(3) . . ?
C13 C22 C43 117.9(2) . . ?
C15 C22 C43 122.1(2) . . ?
N2 C24 C41 114.6(2) . . ?
N2 C24 H24A 108.6 . . ?
C41 C24 H24A 108.6 . . ?
N2 C24 H24B 108.6 . . ?
C41 C24 H24B 108.6 . . ?
H24A C24 H24B 107.6 . . ?
C50 C26 C41 113.9(2) . . ?
C50 C26 H26A 108.8 . . ?
C41 C26 H26A 108.8 . . ?
C50 C26 H26B 108.8 . . ?
C41 C26 H26B 108.8 . . ?
H26A C26 H26B 107.7 . . ?
C15 C35 C45 110.8(2) . . ?
C15 C35 C49 105.9(2) . . ?
C45 C35 C49 109.3(2) . . ?
C15 C35 C16 107.6(2) . . ?
C45 C35 C16 109.0(2) . . ?
C49 C35 C16 114.2(2) . . ?
C40 C39 C13 117.9(3) . . ?
C40 C39 C98 120.8(3) . . ?
C13 C39 C98 121.3(3) . . ?
C39 C40 C42 120.9(3) . . ?
C39 C40 H40A 119.5 . . ?
C42 C40 H40A 119.5 . . ?
C48 C41 C24 109.0(2) . . ?
C48 C41 C26 110.7(2) . . ?
C24 C41 C26 107.5(2) . . ?
C48 C41 C16 113.5(2) . . ?
C24 C41 C16 105.57(19) . . ?
C26 C41 C16 110.2(2) . . ?
C40 C42 C15 121.7(3) . . ?
C40 C42 H42A 119.2 . . ?
C15 C42 H42A 119.2 . . ?
C22 C43 C19 116.0(2) . . ?
C22 C43 H43A 108.3 . . ?
C19 C43 H43A 108.3 . . ?
C22 C43 H43B 108.3 . . ?
C19 C43 H43B 108.3 . . ?
H43A C43 H43B 107.4 . . ?
C50 C45 C35 113.2(2) . . ?
C50 C45 H45A 108.9 . . ?
C35 C45 H45A 108.9 . . ?
C50 C45 H45B 108.9 . . ?
C35 C45 H45B 108.9 . . ?
H45A C45 H45B 107.8 . . ?
C41 C48 H48A 109.5 . . ?
C41 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C41 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C35 C49 H49A 109.5 . . ?
C35 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C35 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C26 C50 C45 110.2(2) . . ?
C26 C50 H50A 109.6 . . ?
C45 C50 H50A 109.6 . . ?
C26 C50 H50B 109.6 . . ?
C45 C50 H50B 109.6 . . ?
H50A C50 H50B 108.1 . . ?
C98 C99 H99A 109.5 . . ?
C98 C99 H99B 109.5 . . ?
H99A C99 H99B 109.5 . . ?
C98 C99 H99C 109.5 . . ?
H99A C99 H99C 109.5 . . ?
H99B C99 H99C 109.5 . . ?
C97 C98 C99 112.3(3) . . ?
C97 C98 C39 112.8(3) . . ?
C99 C98 C39 110.2(2) . . ?
C97 C98 H98A 107.1 . . ?
C99 C98 H98A 107.1 . . ?
C39 C98 H98A 107.1 . . ?
C98 C97 H97A 109.5 . . ?
C98 C97 H97B 109.5 . . ?
H97A C97 H97B 109.5 . . ?
C98 C97 H97C 109.5 . . ?
H97A C97 H97C 109.5 . . ?
H97B C97 H97C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_y1
_database_code_depnum_ccdc_archive 'CCDC 1816224'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H32 N, C5 H3 N2 O4, H2 O'
_chemical_formula_sum            'C25 H37 N3 O5'
_chemical_formula_weight         459.58

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb    '

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

_cell_length_a                   10.3659(9)
_cell_length_b                   7.0531(6)
_cell_length_c                   16.9815(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.543(2)
_cell_angle_gamma                90.00
_cell_volume                     1240.32(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4217
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.57

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   'multi-scan '
_exptl_absorpt_correction_T_min  0.9747
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7879
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3965
_reflns_number_gt                3446
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0634P)²+0.2395P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.6(13)
_refine_ls_number_reflns         3965
_refine_ls_number_parameters     298
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.54269(19) 0.5503(3) 0.40090(12) 0.0364(5) Uani 1 1 d . . .
H1A H 0.5791 0.4416 0.4078 0.044 Uiso 1 1 calc R . .
N2 N 0.3934(2) 0.7618(3) 0.36906(14) 0.0413(5) Uani 1 1 d . . .
N3 N 1.15028(18) -0.0521(4) 0.39402(13) 0.0445(5) Uani 1 1 d . . .
H3A H 1.1469 -0.0407 0.4461 0.067 Uiso 1 1 calc R . .
H3B H 1.2280 -0.0171 0.3791 0.067 Uiso 1 1 calc R . .
H3C H 1.1358 -0.1722 0.3803 0.067 Uiso 1 1 calc R . .
C1 C 0.5985(2) 0.7223(3) 0.41569(14) 0.0306(5) Uani 1 1 d . . .
C2 C 0.4213(2) 0.5801(4) 0.37369(17) 0.0422(6) Uani 1 1 d . . .
H2A H 0.3635 0.4838 0.3597 0.051 Uiso 1 1 calc R . .
C3 C 0.5038(2) 0.8521(3) 0.39600(14) 0.0311(6) Uani 1 1 d . . .
C4 C 0.7340(2) 0.7369(4) 0.44586(14) 0.0369(6) Uani 1 1 d . . .
C5 C 0.5019(2) 1.0608(4) 0.40270(14) 0.0356(6) Uani 1 1 d . . .
C6 C 1.1724(2) 0.1557(5) 0.23775(17) 0.0570(8) Uani 1 1 d . . .
H6A H 1.1925 0.2637 0.2715 0.068 Uiso 1 1 calc R . .
H6B H 1.2417 0.0645 0.2459 0.068 Uiso 1 1 calc R . .
C7 C 1.1715(3) 0.2199(6) 0.1551(2) 0.0664(9) Uani 1 1 d . . .
H7A H 1.1656 0.1102 0.1207 0.080 Uiso 1 1 calc R . .
H7B H 1.2523 0.2839 0.1460 0.080 Uiso 1 1 calc R . .
C8 C 1.0610(3) 0.3522(4) 0.13450(18) 0.0489(7) Uani 1 1 d . . .
H8A H 1.0633 0.3866 0.0793 0.059 Uiso 1 1 calc R . .
H8B H 1.0712 0.4673 0.1654 0.059 Uiso 1 1 calc R . .
C9 C 0.9284(2) 0.2612(4) 0.15021(14) 0.0370(6) Uani 1 1 d . . .
C10 C 0.9318(2) 0.1938(4) 0.23742(14) 0.0341(6) Uani 1 1 d . . .
H10A H 0.9429 0.3099 0.2687 0.041 Uiso 1 1 calc R . .
C11 C 0.7991(2) 0.1185(5) 0.25718(17) 0.0475(7) Uani 1 1 d . . .
H11A H 0.7706 0.0242 0.2187 0.057 Uiso 1 1 calc R . .
H11B H 0.8035 0.0593 0.3088 0.057 Uiso 1 1 calc R . .
C12 C 0.7044(3) 0.2835(5) 0.25642(18) 0.0551(8) Uani 1 1 d . . .
H12A H 0.6174 0.2337 0.2586 0.066 Uiso 1 1 calc R . .
H12B H 0.7214 0.3598 0.3032 0.066 Uiso 1 1 calc R . .
C13 C 0.7119(2) 0.4075(4) 0.18524(15) 0.0444(7) Uani 1 1 d . . .
C14 C 0.8185(2) 0.4060(4) 0.13755(15) 0.0386(6) Uani 1 1 d . . .
C15 C 0.8160(3) 0.5300(4) 0.07341(16) 0.0482(7) Uani 1 1 d . . .
H15A H 0.8856 0.5318 0.0407 0.058 Uiso 1 1 calc R . .
C16 C 0.7127(3) 0.6503(5) 0.05709(17) 0.0518(7) Uani 1 1 d . . .
H16A H 0.7151 0.7320 0.0142 0.062 Uiso 1 1 calc R . .
C17 C 0.6063(3) 0.6515(4) 0.10303(17) 0.0511(7) Uani 1 1 d . . .
C18 C 0.6100(3) 0.5319(5) 0.16696(19) 0.0568(8) Uani 1 1 d . . .
H18A H 0.5408 0.5340 0.2000 0.068 Uiso 1 1 calc R . .
C19 C 1.0504(2) 0.0708(4) 0.35504(15) 0.0427(6) Uani 1 1 d . . .
H19A H 1.0657 0.2006 0.3719 0.051 Uiso 1 1 calc R . .
H19B H 0.9666 0.0333 0.3729 0.051 Uiso 1 1 calc R . .
C20 C 1.0335(3) -0.1415(4) 0.23820(19) 0.0611(9) Uani 1 1 d . . .
H20A H 1.0307 -0.1467 0.1817 0.092 Uiso 1 1 calc R . .
H20B H 0.9555 -0.1945 0.2573 0.092 Uiso 1 1 calc R . .
H20C H 1.1064 -0.2127 0.2588 0.092 Uiso 1 1 calc R . .
C21 C 0.9015(3) 0.1049(4) 0.08865(16) 0.0522(8) Uani 1 1 d . . .
H21A H 0.9009 0.1590 0.0368 0.078 Uiso 1 1 calc R . .
H21B H 0.8191 0.0481 0.0971 0.078 Uiso 1 1 calc R . .
H21C H 0.9678 0.0100 0.0936 0.078 Uiso 1 1 calc R . .
C22 C 0.4924(3) 0.7824(5) 0.0842(2) 0.0625(9) Uani 1 1 d . . .
H22A H 0.4992 0.8230 0.0294 0.075 Uiso 1 1 calc R . .
C23 C 0.4979(4) 0.9562(7) 0.1332(3) 0.1053(17) Uani 1 1 d . . .
H23A H 0.5803 1.0163 0.1288 0.158 Uiso 1 1 calc R . .
H23B H 0.4861 0.9233 0.1873 0.158 Uiso 1 1 calc R . .
H23C H 0.4307 1.0417 0.1154 0.158 Uiso 1 1 calc R . .
C24 C 0.3630(4) 0.6861(7) 0.0895(3) 0.1063(16) Uani 1 1 d . . .
H24A H 0.2954 0.7750 0.0762 0.160 Uiso 1 1 calc R . .
H24B H 0.3535 0.6409 0.1423 0.160 Uiso 1 1 calc R . .
H24C H 0.3579 0.5812 0.0535 0.160 Uiso 1 1 calc R . .
C25 C 1.0462(2) 0.0647(4) 0.26501(14) 0.0376(6) Uani 1 1 d . . .
O1 O 0.79726(16) 0.5878(3) 0.45353(11) 0.0479(5) Uani 1 1 d . . .
O1W O 0.06225(19) 0.5734(3) 0.41852(14) 0.0660(6) Uani 1 1 d . . .
H1WA H -0.0174 0.5836 0.4275 0.099 Uiso 1 1 d R . .
H1WB H 0.0978 0.5122 0.4567 0.099 Uiso 1 1 d R . .
O2 O 0.77680(16) 0.9027(3) 0.46083(12) 0.0486(5) Uani 1 1 d . . .
O3 O 0.60821(16) 1.1455(2) 0.42932(11) 0.0417(4) Uani 1 1 d . . .
H3 H 0.6645 1.0658 0.4387 0.063 Uiso 1 1 calc R . .
O4 O 0.40542(19) 1.1506(3) 0.38522(13) 0.0532(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.337(3) . ?
N1 C1 1.363(3) . ?
N1 H1A 0.8600 . ?
N2 C2 1.315(3) . ?
N2 C3 1.370(3) . ?
N3 C19 1.483(3) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
C1 C3 1.373(3) . ?
C1 C4 1.477(3) . ?
C2 H2A 0.9300 . ?
C3 C5 1.476(3) . ?
C4 O1 1.244(3) . ?
C4 O2 1.272(3) . ?
C5 O4 1.210(3) . ?
C5 O3 1.315(3) . ?
C6 C7 1.474(4) . ?
C6 C25 1.546(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.507(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.551(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C21 1.536(4) . ?
C9 C14 1.538(3) . ?
C9 C10 1.554(3) . ?
C10 C11 1.526(3) . ?
C10 C25 1.551(3) . ?
C10 H10A 0.9800 . ?
C11 C12 1.522(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.497(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.397(4) . ?
C13 C14 1.399(3) . ?
C14 C15 1.396(4) . ?
C15 C16 1.384(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.379(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.374(4) . ?
C17 C22 1.521(4) . ?
C18 H18A 0.9300 . ?
C19 C25 1.528(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C25 1.527(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.482(6) . ?
C22 C24 1.509(5) . ?
C22 H22A 0.9800 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8500 . ?
O3 H3 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 108.0(2) . . ?
C2 N1 H1A 126.0 . . ?
C1 N1 H1A 126.0 . . ?
C2 N2 C3 104.8(2) . . ?
C19 N3 H3A 109.5 . . ?
C19 N3 H3B 109.5 . . ?
H3A N3 H3B 109.5 . . ?
C19 N3 H3C 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
N1 C1 C3 104.8(2) . . ?
N1 C1 C4 121.0(2) . . ?
C3 C1 C4 134.1(2) . . ?
N2 C2 N1 112.0(2) . . ?
N2 C2 H2A 124.0 . . ?
N1 C2 H2A 124.0 . . ?
N2 C3 C1 110.4(2) . . ?
N2 C3 C5 118.4(2) . . ?
C1 C3 C5 131.2(2) . . ?
O1 C4 O2 125.4(2) . . ?
O1 C4 C1 117.8(2) . . ?
O2 C4 C1 116.8(2) . . ?
O4 C5 O3 121.2(2) . . ?
O4 C5 C3 121.1(2) . . ?
O3 C5 C3 117.7(2) . . ?
C7 C6 C25 116.3(2) . . ?
C7 C6 H6A 108.2 . . ?
C25 C6 H6A 108.2 . . ?
C7 C6 H6B 108.2 . . ?
C25 C6 H6B 108.2 . . ?
H6A C6 H6B 107.4 . . ?
C6 C7 C8 112.6(2) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C9 112.0(3) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C21 C9 C14 105.7(2) . . ?
C21 C9 C8 108.4(2) . . ?
C14 C9 C8 111.0(2) . . ?
C21 C9 C10 115.1(2) . . ?
C14 C9 C10 108.77(19) . . ?
C8 C9 C10 107.9(2) . . ?
C11 C10 C25 114.5(2) . . ?
C11 C10 C9 109.5(2) . . ?
C25 C10 C9 116.88(18) . . ?
C11 C10 H10A 104.9 . . ?
C25 C10 H10A 104.9 . . ?
C9 C10 H10A 104.9 . . ?
C12 C11 C10 108.6(2) . . ?
C12 C11 H11A 110.0 . . ?
C10 C11 H11A 110.0 . . ?
C12 C11 H11B 110.0 . . ?
C10 C11 H11B 110.0 . . ?
H11A C11 H11B 108.3 . . ?
C13 C12 C11 113.4(2) . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C18 C13 C14 119.0(2) . . ?
C18 C13 C12 118.8(2) . . ?
C14 C13 C12 122.2(2) . . ?
C15 C14 C13 117.3(2) . . ?
C15 C14 C9 120.9(2) . . ?
C13 C14 C9 121.6(2) . . ?
C16 C15 C14 121.9(2) . . ?
C16 C15 H15A 119.1 . . ?
C14 C15 H15A 119.1 . . ?
C17 C16 C15 121.4(3) . . ?
C17 C16 H16A 119.3 . . ?
C15 C16 H16A 119.3 . . ?
C18 C17 C16 116.6(3) . . ?
C18 C17 C22 122.2(3) . . ?
C16 C17 C22 121.2(3) . . ?
C17 C18 C13 123.8(3) . . ?
C17 C18 H18A 118.1 . . ?
C13 C18 H18A 118.1 . . ?
N3 C19 C25 114.7(2) . . ?
N3 C19 H19A 108.6 . . ?
C25 C19 H19A 108.6 . . ?
N3 C19 H19B 108.6 . . ?
C25 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
C25 C20 H20A 109.5 . . ?
C25 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C25 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 C21 H21A 109.5 . . ?
C9 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C9 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C24 110.5(4) . . ?
C23 C22 C17 112.0(3) . . ?
C24 C22 C17 113.4(3) . . ?
C23 C22 H22A 106.8 . . ?
C24 C22 H22A 106.8 . . ?
C17 C22 H22A 106.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 C25 C19 108.9(2) . . ?
C20 C25 C6 111.7(3) . . ?
C19 C25 C6 107.5(2) . . ?
C20 C25 C10 114.4(2) . . ?
C19 C25 C10 105.83(19) . . ?
C6 C25 C10 108.1(2) . . ?
H1WA O1W H1WB 107.3 . . ?
C5 O3 H3 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.036
