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

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

data_ja
_database_code_depnum_ccdc_archive 'CCDC 1571120'
_audit_update_record             
;
2017-08-27 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2.41 H2.24 N0.22 O0.22'
_chemical_formula_weight         37.86

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   19.078(2)
_cell_length_b                   17.996(2)
_cell_length_c                   20.823(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7149.0(15)
_cell_formula_units_Z            143
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6780
_cell_measurement_theta_min      1.84
_cell_measurement_theta_max      25.68

_exptl_crystal_description       BAR
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2864
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31791
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0568
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         25.68
_reflns_number_total             6780
_reflns_number_gt                3492
_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)+(0.0745P)²+0.0845P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6780
_refine_ls_number_parameters     460
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1495
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
O4 O 0.15900(8) 0.39921(8) 0.07150(7) 0.0581(5) Uani 1 1 d . . .
O3 O 0.20411(8) 0.40081(9) 0.28931(8) 0.0593(5) Uani 1 1 d . . .
N3 N 0.20825(9) 0.51940(10) 0.32906(9) 0.0505(5) Uani 1 1 d . . .
N4 N 0.18109(11) 0.59275(10) 0.10324(9) 0.0510(5) Uani 1 1 d . . .
N2 N 0.24117(9) 0.41582(10) 0.14514(9) 0.0505(5) Uani 1 1 d . . .
N1 N 0.32289(9) 0.46404(10) 0.21518(8) 0.0518(5) Uani 1 1 d . . .
H1A H 0.3639 0.4785 0.2269 0.062 Uiso 1 1 calc R . .
O2 O 0.29446(9) 0.55280(10) 0.08881(8) 0.0683(5) Uani 1 1 d . . .
C40 C 0.21951(11) 0.46613(14) 0.28411(11) 0.0471(6) Uani 1 1 d . . .
C39 C 0.13722(11) 0.50151(12) 0.16797(10) 0.0415(5) Uani 1 1 d . . .
C38 C 0.26365(11) 0.58207(12) 0.24829(11) 0.0455(6) Uani 1 1 d . . .
C37 C 0.12124(12) 0.56554(12) 0.13433(11) 0.0462(6) Uani 1 1 d . . .
C36 C 0.30617(11) 0.39686(13) 0.18049(11) 0.0504(6) Uani 1 1 d . . .
H36A H 0.2960 0.3572 0.2113 0.060 Uiso 1 1 calc R . .
C45 C 0.23680(14) 0.54758(13) 0.11308(11) 0.0506(6) Uani 1 1 d . . .
O1 O 0.22898(9) 0.30325(10) 0.10009(9) 0.0820(6) Uani 1 1 d . . .
C35 C 0.25656(11) 0.50284(12) 0.22648(10) 0.0445(6) Uani 1 1 d . . .
C34 C 0.21470(11) 0.48850(12) 0.16231(10) 0.0441(6) Uani 1 1 d . . .
C33 C 0.15898(12) 0.65188(13) -0.00245(11) 0.0516(6) Uani 1 1 d . . .
C32 C 0.29253(11) 0.64397(14) 0.21999(12) 0.0551(6) Uani 1 1 d . . .
H32A H 0.3133 0.6408 0.1797 0.066 Uiso 1 1 calc R . .
C31 C 0.23380(11) 0.58824(13) 0.30865(12) 0.0486(6) Uani 1 1 d . . .
C30 C 0.08484(13) 0.46328(13) 0.19860(11) 0.0550(6) Uani 1 1 d . . .
H30A H 0.0946 0.4197 0.2209 0.066 Uiso 1 1 calc R . .
C29 C 0.42167(12) 0.32901(14) 0.17201(12) 0.0537(6) Uani 1 1 d . . .
C28 C 0.16304(13) 0.58574(15) -0.03525(13) 0.0658(7) Uani 1 1 d . . .
H28A H 0.1797 0.5435 -0.0145 0.079 Uiso 1 1 calc R . .
C27 C 0.40458(13) 0.26877(15) 0.20916(12) 0.0619(7) Uani 1 1 d . . .
H27A H 0.3577 0.2557 0.2135 0.074 Uiso 1 1 calc R . .
C26 C 0.18473(14) 0.65983(13) 0.06504(12) 0.0657(7) Uani 1 1 d . . .
H26A H 0.2331 0.6765 0.0639 0.079 Uiso 1 1 calc R . .
H26B H 0.1574 0.6982 0.0862 0.079 Uiso 1 1 calc R . .
C25 C 0.29016(12) 0.71095(14) 0.25247(14) 0.0630(7) Uani 1 1 d . . .
H25A H 0.3091 0.7532 0.2335 0.076 Uiso 1 1 calc R . .
C24 C 0.23129(12) 0.65477(14) 0.34128(13) 0.0617(7) Uani 1 1 d . . .
H24A H 0.2107 0.6582 0.3816 0.074 Uiso 1 1 calc R . .
C23 C 0.21051(13) 0.36696(14) 0.10521(12) 0.0553(6) Uani 1 1 d . . .
C22 C 0.17915(13) 0.50481(14) 0.39207(11) 0.0629(7) Uani 1 1 d . . .
H22A H 0.2114 0.5234 0.4243 0.075 Uiso 1 1 calc R . .
H22B H 0.1754 0.4515 0.3979 0.075 Uiso 1 1 calc R . .
C21 C 0.01668(13) 0.49098(17) 0.19570(13) 0.0673(8) Uani 1 1 d . . .
H21A H -0.0194 0.4655 0.2161 0.081 Uiso 1 1 calc R . .
C17 C 0.05434(14) 0.59360(15) 0.13159(12) 0.0627(7) Uani 1 1 d . . .
H17A H 0.0445 0.6370 0.1091 0.075 Uiso 1 1 calc R . .
C16 C 0.10840(13) 0.53918(13) 0.40328(12) 0.0548(6) Uani 1 1 d . . .
C15 C 0.26058(14) 0.71611(15) 0.31182(15) 0.0696(8) Uani 1 1 d . . .
H15A H 0.2601 0.7617 0.3329 0.084 Uiso 1 1 calc R . .
C14 C 0.36602(12) 0.37275(14) 0.13767(11) 0.0598(7) Uani 1 1 d . . .
H14A H 0.3474 0.3427 0.1029 0.072 Uiso 1 1 calc R . .
H14B H 0.3873 0.4165 0.1188 0.072 Uiso 1 1 calc R . .
C13 C 0.49152(15) 0.34630(16) 0.16627(14) 0.0792(8) Uani 1 1 d . . .
H13A H 0.5049 0.3873 0.1420 0.095 Uiso 1 1 calc R . .
C12 C 0.00244(14) 0.55516(18) 0.16326(14) 0.0725(8) Uani 1 1 d . . .
H12A H -0.0432 0.5733 0.1626 0.087 Uiso 1 1 calc R . .
C11 C 0.52326(19) 0.2448(2) 0.23361(17) 0.0947(11) Uani 1 1 d . . .
H11A H 0.5573 0.2169 0.2546 0.114 Uiso 1 1 calc R . .
C10 C 0.11291(16) 0.7078(2) -0.09748(17) 0.0927(10) Uani 1 1 d . . .
H10A H 0.0957 0.7496 -0.1184 0.111 Uiso 1 1 calc R . .
C9 C 0.13330(14) 0.71289(15) -0.03391(15) 0.0749(8) Uani 1 1 d . . .
H9A H 0.1296 0.7580 -0.0124 0.090 Uiso 1 1 calc R . .
C8 C 0.14264(14) 0.58134(19) -0.09881(15) 0.0793(9) Uani 1 1 d . . .
H8A H 0.1460 0.5363 -0.1205 0.095 Uiso 1 1 calc R . .
C19 C 0.06039(16) 0.54848(16) 0.35583(14) 0.0770(8) Uani 1 1 d . . .
H19A H 0.0720 0.5352 0.3140 0.092 Uiso 1 1 calc R . .
C7 C 0.10741(14) 0.35445(16) 0.03577(13) 0.0699(8) Uani 1 1 d . . .
C6 C 0.05148(15) 0.41074(18) 0.02001(14) 0.0875(9) Uani 1 1 d . . .
H6A H 0.0303 0.4281 0.0590 0.131 Uiso 1 1 calc R . .
H6B H 0.0164 0.3881 -0.0066 0.131 Uiso 1 1 calc R . .
H6C H 0.0722 0.4519 -0.0024 0.131 Uiso 1 1 calc R . .
C5 C 0.45475(17) 0.22702(16) 0.24028(13) 0.0779(9) Uani 1 1 d . . .
H5A H 0.4416 0.1869 0.2657 0.093 Uiso 1 1 calc R . .
C4 C 0.11778(16) 0.6421(3) -0.12971(15) 0.0923(11) Uani 1 1 d . . .
H4A H 0.1042 0.6391 -0.1725 0.111 Uiso 1 1 calc R . .
C3 C 0.54263(16) 0.3032(2) 0.19637(19) 0.0972(11) Uani 1 1 d . . .
H3A H 0.5898 0.3144 0.1909 0.117 Uiso 1 1 calc R . .
C18 C -0.00456(16) 0.57700(17) 0.36825(18) 0.0855(9) Uani 1 1 d . . .
H18A H -0.0364 0.5831 0.3348 0.103 Uiso 1 1 calc R . .
C43 C -0.02303(18) 0.59635(18) 0.4282(2) 0.0968(11) Uani 1 1 d . . .
H43A H -0.0678 0.6142 0.4367 0.116 Uiso 1 1 calc R . .
C44 C 0.08970(18) 0.5607(2) 0.46370(14) 0.0994(11) Uani 1 1 d . . .
H44A H 0.1217 0.5558 0.4971 0.119 Uiso 1 1 calc R . .
C2 C 0.14191(18) 0.3243(2) -0.02349(16) 0.1376(15) Uani 1 1 d . . .
H2A H 0.1766 0.2882 -0.0115 0.206 Uiso 1 1 calc R . .
H2B H 0.1640 0.3642 -0.0465 0.206 Uiso 1 1 calc R . .
H2C H 0.1073 0.3013 -0.0503 0.206 Uiso 1 1 calc R . .
C1 C 0.07800(17) 0.29493(18) 0.07911(17) 0.1121(12) Uani 1 1 d . . .
H1B H 0.1138 0.2591 0.0884 0.168 Uiso 1 1 calc R . .
H1C H 0.0395 0.2708 0.0581 0.168 Uiso 1 1 calc R . .
H1D H 0.0620 0.3171 0.1184 0.168 Uiso 1 1 calc R . .
C46 C 0.0246(2) 0.5895(3) 0.47602(19) 0.1317(15) Uani 1 1 d . . .
H46A H 0.0130 0.6044 0.5175 0.158 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
O4 C23 1.340(3) . ?
O4 C7 1.473(3) . ?
O3 C40 1.216(3) . ?
N3 C40 1.357(3) . ?
N3 C31 1.398(3) . ?
N3 C22 1.449(3) . ?
N4 C45 1.354(3) . ?
N4 C37 1.401(3) . ?
N4 C26 1.447(3) . ?
N2 C23 1.344(3) . ?
N2 C34 1.447(3) . ?
N2 C36 1.482(3) . ?
N1 C36 1.444(3) . ?
N1 C35 1.464(3) . ?
N1 H1A 0.8600 . ?
O2 C45 1.214(3) . ?
C40 C35 1.541(3) . ?
C39 C30 1.371(3) . ?
C39 C37 1.383(3) . ?
C39 C34 1.501(3) . ?
C38 C32 1.375(3) . ?
C38 C31 1.384(3) . ?
C38 C35 1.503(3) . ?
C37 C17 1.374(3) . ?
C36 C14 1.512(3) . ?
C36 H36A 0.9800 . ?
C45 C34 1.536(3) . ?
O1 C23 1.204(3) . ?
C35 C34 1.578(3) . ?
C33 C9 1.369(3) . ?
C33 C28 1.374(3) . ?
C33 C26 1.496(3) . ?
C32 C25 1.383(3) . ?
C32 H32A 0.9300 . ?
C31 C24 1.378(3) . ?
C30 C21 1.394(3) . ?
C30 H30A 0.9300 . ?
C29 C27 1.371(3) . ?
C29 C13 1.374(3) . ?
C29 C14 1.502(3) . ?
C28 C8 1.382(4) . ?
C28 H28A 0.9300 . ?
C27 C5 1.379(3) . ?
C27 H27A 0.9300 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C25 C15 1.362(3) . ?
C25 H25A 0.9300 . ?
C24 C15 1.381(3) . ?
C24 H24A 0.9300 . ?
C22 C16 1.503(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C21 C12 1.365(4) . ?
C21 H21A 0.9300 . ?
C17 C12 1.376(4) . ?
C17 H17A 0.9300 . ?
C16 C19 1.358(3) . ?
C16 C44 1.364(3) . ?
C15 H15A 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C13 C3 1.395(4) . ?
C13 H13A 0.9300 . ?
C12 H12A 0.9300 . ?
C11 C5 1.353(4) . ?
C11 C3 1.357(4) . ?
C11 H11A 0.9300 . ?
C10 C4 1.362(4) . ?
C10 C9 1.383(4) . ?
C10 H10A 0.9300 . ?
C9 H9A 0.9300 . ?
C8 C4 1.355(4) . ?
C8 H8A 0.9300 . ?
C19 C18 1.366(4) . ?
C19 H19A 0.9300 . ?
C7 C2 1.500(4) . ?
C7 C6 1.508(4) . ?
C7 C1 1.509(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C5 H5A 0.9300 . ?
C4 H4A 0.9300 . ?
C3 H3A 0.9300 . ?
C18 C43 1.342(4) . ?
C18 H18A 0.9300 . ?
C43 C46 1.354(5) . ?
C43 H43A 0.9300 . ?
C44 C46 1.370(4) . ?
C44 H44A 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
C46 H46A 0.9300 . ?

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
C23 O4 C7 121.17(19) . . ?
C40 N3 C31 111.17(19) . . ?
C40 N3 C22 123.9(2) . . ?
C31 N3 C22 124.73(19) . . ?
C45 N4 C37 111.1(2) . . ?
C45 N4 C26 123.1(2) . . ?
C37 N4 C26 125.8(2) . . ?
C23 N2 C34 126.33(19) . . ?
C23 N2 C36 121.38(19) . . ?
C34 N2 C36 112.18(16) . . ?
C36 N1 C35 106.78(16) . . ?
C36 N1 H1A 126.6 . . ?
C35 N1 H1A 126.6 . . ?
O3 C40 N3 125.7(2) . . ?
O3 C40 C35 126.5(2) . . ?
N3 C40 C35 107.9(2) . . ?
C30 C39 C37 119.6(2) . . ?
C30 C39 C34 132.5(2) . . ?
C37 C39 C34 107.90(19) . . ?
C32 C38 C31 119.3(2) . . ?
C32 C38 C35 132.5(2) . . ?
C31 C38 C35 108.27(19) . . ?
C17 C37 C39 122.2(2) . . ?
C17 C37 N4 127.6(2) . . ?
C39 C37 N4 110.22(19) . . ?
N1 C36 N2 103.92(16) . . ?
N1 C36 C14 111.6(2) . . ?
N2 C36 C14 113.90(19) . . ?
N1 C36 H36A 109.1 . . ?
N2 C36 H36A 109.1 . . ?
C14 C36 H36A 109.1 . . ?
O2 C45 N4 127.0(2) . . ?
O2 C45 C34 125.5(2) . . ?
N4 C45 C34 107.5(2) . . ?
N1 C35 C38 115.04(18) . . ?
N1 C35 C40 108.49(17) . . ?
C38 C35 C40 102.28(18) . . ?
N1 C35 C34 102.90(16) . . ?
C38 C35 C34 117.18(17) . . ?
C40 C35 C34 110.93(17) . . ?
N2 C34 C39 120.26(18) . . ?
N2 C34 C45 111.41(19) . . ?
C39 C34 C45 102.40(18) . . ?
N2 C34 C35 100.40(16) . . ?
C39 C34 C35 113.98(17) . . ?
C45 C34 C35 108.25(17) . . ?
C9 C33 C28 118.5(2) . . ?
C9 C33 C26 119.4(2) . . ?
C28 C33 C26 122.1(2) . . ?
C38 C32 C25 118.9(2) . . ?
C38 C32 H32A 120.5 . . ?
C25 C32 H32A 120.5 . . ?
C24 C31 C38 122.1(2) . . ?
C24 C31 N3 127.5(2) . . ?
C38 C31 N3 110.40(19) . . ?
C39 C30 C21 118.7(2) . . ?
C39 C30 H30A 120.6 . . ?
C21 C30 H30A 120.6 . . ?
C27 C29 C13 117.3(2) . . ?
C27 C29 C14 121.0(2) . . ?
C13 C29 C14 121.7(3) . . ?
C33 C28 C8 120.7(3) . . ?
C33 C28 H28A 119.7 . . ?
C8 C28 H28A 119.7 . . ?
C29 C27 C5 122.1(3) . . ?
C29 C27 H27A 119.0 . . ?
C5 C27 H27A 119.0 . . ?
N4 C26 C33 114.90(19) . . ?
N4 C26 H26A 108.5 . . ?
C33 C26 H26A 108.5 . . ?
N4 C26 H26B 108.5 . . ?
C33 C26 H26B 108.5 . . ?
H26A C26 H26B 107.5 . . ?
C15 C25 C32 121.1(2) . . ?
C15 C25 H25A 119.4 . . ?
C32 C25 H25A 119.4 . . ?
C31 C24 C15 117.5(2) . . ?
C31 C24 H24A 121.3 . . ?
C15 C24 H24A 121.3 . . ?
O1 C23 O4 125.5(2) . . ?
O1 C23 N2 123.4(2) . . ?
O4 C23 N2 111.1(2) . . ?
N3 C22 C16 114.2(2) . . ?
N3 C22 H22A 108.7 . . ?
C16 C22 H22A 108.7 . . ?
N3 C22 H22B 108.7 . . ?
C16 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C12 C21 C30 120.6(3) . . ?
C12 C21 H21A 119.7 . . ?
C30 C21 H21A 119.7 . . ?
C37 C17 C12 117.6(3) . . ?
C37 C17 H17A 121.2 . . ?
C12 C17 H17A 121.2 . . ?
C19 C16 C44 117.4(3) . . ?
C19 C16 C22 122.9(2) . . ?
C44 C16 C22 119.7(2) . . ?
C25 C15 C24 121.1(2) . . ?
C25 C15 H15A 119.5 . . ?
C24 C15 H15A 119.5 . . ?
C29 C14 C36 113.8(2) . . ?
C29 C14 H14A 108.8 . . ?
C36 C14 H14A 108.8 . . ?
C29 C14 H14B 108.8 . . ?
C36 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C29 C13 C3 120.9(3) . . ?
C29 C13 H13A 119.6 . . ?
C3 C13 H13A 119.6 . . ?
C21 C12 C17 121.3(3) . . ?
C21 C12 H12A 119.4 . . ?
C17 C12 H12A 119.4 . . ?
C5 C11 C3 120.3(3) . . ?
C5 C11 H11A 119.8 . . ?
C3 C11 H11A 119.8 . . ?
C4 C10 C9 120.6(3) . . ?
C4 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C33 C9 C10 120.4(3) . . ?
C33 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C4 C8 C28 120.5(3) . . ?
C4 C8 H8A 119.8 . . ?
C28 C8 H8A 119.8 . . ?
C16 C19 C18 121.4(3) . . ?
C16 C19 H19A 119.3 . . ?
C18 C19 H19A 119.3 . . ?
O4 C7 C2 108.7(2) . . ?
O4 C7 C6 102.4(2) . . ?
C2 C7 C6 112.0(3) . . ?
O4 C7 C1 109.5(2) . . ?
C2 C7 C1 113.5(3) . . ?
C6 C7 C1 110.1(3) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C11 C5 C27 119.6(3) . . ?
C11 C5 H5A 120.2 . . ?
C27 C5 H5A 120.2 . . ?
C8 C4 C10 119.4(3) . . ?
C8 C4 H4A 120.3 . . ?
C10 C4 H4A 120.3 . . ?
C11 C3 C13 119.8(3) . . ?
C11 C3 H3A 120.1 . . ?
C13 C3 H3A 120.1 . . ?
C43 C18 C19 120.8(3) . . ?
C43 C18 H18A 119.6 . . ?
C19 C18 H18A 119.6 . . ?
C18 C43 C46 119.0(3) . . ?
C18 C43 H43A 120.5 . . ?
C46 C43 H43A 120.5 . . ?
C16 C44 C46 121.2(3) . . ?
C16 C44 H44A 119.4 . . ?
C46 C44 H44A 119.4 . . ?
C7 C2 H2A 109.5 . . ?
C7 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C7 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C7 C1 H1B 109.5 . . ?
C7 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C1 H1D 109.5 . . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
C43 C46 C44 120.3(3) . . ?
C43 C46 H46A 119.8 . . ?
C44 C46 H46A 119.8 . . ?

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
C31 N3 C40 O3 178.4(2) . . . . ?
C22 N3 C40 O3 3.5(3) . . . . ?
C31 N3 C40 C35 -0.3(2) . . . . ?
C22 N3 C40 C35 -175.23(18) . . . . ?
C30 C39 C37 C17 1.5(3) . . . . ?
C34 C39 C37 C17 -178.4(2) . . . . ?
C30 C39 C37 N4 -175.92(18) . . . . ?
C34 C39 C37 N4 4.2(2) . . . . ?
C45 N4 C37 C17 -175.2(2) . . . . ?
C26 N4 C37 C17 4.5(3) . . . . ?
C45 N4 C37 C39 2.1(2) . . . . ?
C26 N4 C37 C39 -178.23(19) . . . . ?
C35 N1 C36 N2 27.7(2) . . . . ?
C35 N1 C36 C14 150.90(18) . . . . ?
C23 N2 C36 N1 177.8(2) . . . . ?
C34 N2 C36 N1 -5.9(2) . . . . ?
C23 N2 C36 C14 56.1(3) . . . . ?
C34 N2 C36 C14 -127.5(2) . . . . ?
C37 N4 C45 O2 174.1(2) . . . . ?
C26 N4 C45 O2 -5.6(4) . . . . ?
C37 N4 C45 C34 -7.2(2) . . . . ?
C26 N4 C45 C34 173.05(18) . . . . ?
C36 N1 C35 C38 -166.48(18) . . . . ?
C36 N1 C35 C40 79.7(2) . . . . ?
C36 N1 C35 C34 -37.9(2) . . . . ?
C32 C38 C35 N1 61.9(3) . . . . ?
C31 C38 C35 N1 -118.2(2) . . . . ?
C32 C38 C35 C40 179.3(2) . . . . ?
C31 C38 C35 C40 -0.9(2) . . . . ?
C32 C38 C35 C34 -59.2(3) . . . . ?
C31 C38 C35 C34 120.6(2) . . . . ?
O3 C40 C35 N1 -56.0(3) . . . . ?
N3 C40 C35 N1 122.66(18) . . . . ?
O3 C40 C35 C38 -178.0(2) . . . . ?
N3 C40 C35 C38 0.7(2) . . . . ?
O3 C40 C35 C34 56.3(3) . . . . ?
N3 C40 C35 C34 -125.01(18) . . . . ?
C23 N2 C34 C39 34.1(3) . . . . ?
C36 N2 C34 C39 -142.1(2) . . . . ?
C23 N2 C34 C45 -85.6(3) . . . . ?
C36 N2 C34 C45 98.2(2) . . . . ?
C23 N2 C34 C35 159.9(2) . . . . ?
C36 N2 C34 C35 -16.2(2) . . . . ?
C30 C39 C34 N2 48.1(3) . . . . ?
C37 C39 C34 N2 -132.0(2) . . . . ?
C30 C39 C34 C45 172.2(2) . . . . ?
C37 C39 C34 C45 -7.9(2) . . . . ?
C30 C39 C34 C35 -71.1(3) . . . . ?
C37 C39 C34 C35 108.7(2) . . . . ?
O2 C45 C34 N2 -42.3(3) . . . . ?
N4 C45 C34 N2 138.96(18) . . . . ?
O2 C45 C34 C39 -172.1(2) . . . . ?
N4 C45 C34 C39 9.1(2) . . . . ?
O2 C45 C34 C35 67.2(3) . . . . ?
N4 C45 C34 C35 -111.57(19) . . . . ?
N1 C35 C34 N2 32.1(2) . . . . ?
C38 C35 C34 N2 159.33(18) . . . . ?
C40 C35 C34 N2 -83.8(2) . . . . ?
N1 C35 C34 C39 162.02(18) . . . . ?
C38 C35 C34 C39 -70.7(2) . . . . ?
C40 C35 C34 C39 46.2(2) . . . . ?
N1 C35 C34 C45 -84.8(2) . . . . ?
C38 C35 C34 C45 42.5(3) . . . . ?
C40 C35 C34 C45 159.39(19) . . . . ?
C31 C38 C32 C25 -0.7(3) . . . . ?
C35 C38 C32 C25 179.1(2) . . . . ?
C32 C38 C31 C24 0.7(3) . . . . ?
C35 C38 C31 C24 -179.1(2) . . . . ?
C32 C38 C31 N3 -179.39(19) . . . . ?
C35 C38 C31 N3 0.8(2) . . . . ?
C40 N3 C31 C24 179.6(2) . . . . ?
C22 N3 C31 C24 -5.5(3) . . . . ?
C40 N3 C31 C38 -0.3(2) . . . . ?
C22 N3 C31 C38 174.59(19) . . . . ?
C37 C39 C30 C21 -1.0(3) . . . . ?
C34 C39 C30 C21 178.9(2) . . . . ?
C9 C33 C28 C8 1.0(4) . . . . ?
C26 C33 C28 C8 -176.1(2) . . . . ?
C13 C29 C27 C5 0.6(4) . . . . ?
C14 C29 C27 C5 178.9(2) . . . . ?
C45 N4 C26 C33 98.5(3) . . . . ?
C37 N4 C26 C33 -81.2(3) . . . . ?
C9 C33 C26 N4 153.6(2) . . . . ?
C28 C33 C26 N4 -29.3(3) . . . . ?
C38 C32 C25 C15 0.7(3) . . . . ?
C38 C31 C24 C15 -0.7(3) . . . . ?
N3 C31 C24 C15 179.5(2) . . . . ?
C7 O4 C23 O1 15.8(4) . . . . ?
C7 O4 C23 N2 -165.9(2) . . . . ?
C34 N2 C23 O1 -168.3(2) . . . . ?
C36 N2 C23 O1 7.5(4) . . . . ?
C34 N2 C23 O4 13.4(3) . . . . ?
C36 N2 C23 O4 -170.81(19) . . . . ?
C40 N3 C22 C16 -114.3(2) . . . . ?
C31 N3 C22 C16 71.5(3) . . . . ?
C39 C30 C21 C12 -0.3(3) . . . . ?
C39 C37 C17 C12 -0.7(3) . . . . ?
N4 C37 C17 C12 176.3(2) . . . . ?
N3 C22 C16 C19 32.4(3) . . . . ?
N3 C22 C16 C44 -149.3(3) . . . . ?
C32 C25 C15 C24 -0.7(4) . . . . ?
C31 C24 C15 C25 0.6(4) . . . . ?
C27 C29 C14 C36 51.1(3) . . . . ?
C13 C29 C14 C36 -130.6(2) . . . . ?
N1 C36 C14 C29 83.0(3) . . . . ?
N2 C36 C14 C29 -159.7(2) . . . . ?
C27 C29 C13 C3 1.0(4) . . . . ?
C14 C29 C13 C3 -177.3(2) . . . . ?
C30 C21 C12 C17 1.2(4) . . . . ?
C37 C17 C12 C21 -0.7(4) . . . . ?
C28 C33 C9 C10 -0.8(4) . . . . ?
C26 C33 C9 C10 176.3(2) . . . . ?
C4 C10 C9 C33 0.2(4) . . . . ?
C33 C28 C8 C4 -0.5(4) . . . . ?
C44 C16 C19 C18 -1.2(4) . . . . ?
C22 C16 C19 C18 177.1(3) . . . . ?
C23 O4 C7 C2 -74.8(3) . . . . ?
C23 O4 C7 C6 166.6(2) . . . . ?
C23 O4 C7 C1 49.7(3) . . . . ?
C3 C11 C5 C27 -0.2(5) . . . . ?
C29 C27 C5 C11 -1.0(4) . . . . ?
C28 C8 C4 C10 -0.1(4) . . . . ?
C9 C10 C4 C8 0.3(5) . . . . ?
C5 C11 C3 C13 1.8(5) . . . . ?
C29 C13 C3 C11 -2.2(4) . . . . ?
C16 C19 C18 C43 -0.4(5) . . . . ?
C19 C18 C43 C46 2.2(5) . . . . ?
C19 C16 C44 C46 1.0(5) . . . . ?
C22 C16 C44 C46 -177.4(3) . . . . ?
C18 C43 C46 C44 -2.3(6) . . . . ?
C16 C44 C46 C43 0.8(6) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_ja_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1571121'
_audit_update_record             
;
2017-08-27 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H36 N4 O4'
_chemical_formula_weight         552.66

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   10.1477(4)
_cell_length_b                   21.6478(8)
_cell_length_c                   13.5815(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.959(2)
_cell_angle_gamma                90.00
_cell_volume                     2972.35(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5654
_cell_measurement_theta_min      1.88
_cell_measurement_theta_max      25.68

_exptl_crystal_description       BAR
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18147
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         25.68
_reflns_number_total             5654
_reflns_number_gt                3959
_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)+(0.0877P)²+2.3925P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5654
_refine_ls_number_parameters     357
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0694
_refine_ls_wR_factor_ref         0.1996
_refine_ls_wR_factor_gt          0.1781
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.47559(19) 0.12451(11) 0.85493(14) 0.0578(6) Uani 1 1 d . . .
O3 O 0.55141(17) 0.12927(10) 0.70248(14) 0.0539(5) Uani 1 1 d U . .
O1 O 0.1661(2) 0.23863(11) 0.72281(15) 0.0633(6) Uani 1 1 d . . .
N1 N 0.3365(2) 0.12116(11) 0.71645(15) 0.0420(5) Uani 1 1 d . . .
O2 O 0.2850(2) 0.02536(10) 0.56461(16) 0.0596(6) Uani 1 1 d . . .
C15 C 0.3007(2) 0.13461(12) 0.61237(17) 0.0370(6) Uani 1 1 d . . .
C13 C 0.3749(2) 0.18446(13) 0.56144(18) 0.0393(6) Uani 1 1 d . . .
C14 C 0.4228(2) 0.15871(14) 0.47795(19) 0.0453(7) Uani 1 1 d . . .
C6 C 0.0612(2) 0.14151(13) 0.52016(19) 0.0425(6) Uani 1 1 d . . .
N4 N 0.1098(2) 0.10516(12) 0.69309(16) 0.0485(6) Uani 1 1 d . . .
H4A H 0.0360 0.0857 0.6937 0.058 Uiso 1 1 calc R . .
N2 N 0.3904(2) 0.09564(12) 0.47152(16) 0.0486(6) Uani 1 1 d . . .
C32 C 0.4577(2) 0.12580(13) 0.76590(19) 0.0420(6) Uani 1 1 d . . .
C26 C 0.2327(3) 0.03944(14) 0.81485(19) 0.0476(7) Uani 1 1 d . . .
H26A H 0.3081 0.0393 0.8639 0.057 Uiso 1 1 calc R . .
H26B H 0.2507 0.0100 0.7638 0.057 Uiso 1 1 calc R . .
C16 C 0.3228(3) 0.07773(14) 0.54840(19) 0.0433(6) Uani 1 1 d . . .
C7 C 0.1478(2) 0.14653(13) 0.61554(18) 0.0394(6) Uani 1 1 d . . .
C27 C 0.2199(2) 0.10290(14) 0.76933(19) 0.0431(6) Uani 1 1 d . . .
H27 H 0.2060 0.1334 0.8207 0.052 Uiso 1 1 calc R . .
N3 N 0.0505(3) 0.24169(12) 0.57051(18) 0.0568(7) Uani 1 1 d . . .
C12 C 0.3981(3) 0.24574(14) 0.5827(2) 0.0531(7) Uani 1 1 d . . .
H12 H 0.3678 0.2637 0.6387 0.064 Uiso 1 1 calc R . .
C5 C 0.0071(3) 0.19919(15) 0.4974(2) 0.0499(7) Uani 1 1 d . . .
C8 C 0.1249(3) 0.21414(14) 0.6455(2) 0.0468(7) Uani 1 1 d . . .
C33 C 0.4941(3) 0.19236(18) 0.4148(2) 0.0585(8) Uani 1 1 d . . .
H33 H 0.5267 0.1742 0.3598 0.070 Uiso 1 1 calc R . .
C18 C 0.3753(3) 0.06698(15) 0.2938(2) 0.0567(8) Uani 1 1 d . . .
C10 C 0.5152(3) 0.25363(19) 0.4362(2) 0.0677(10) Uani 1 1 d . . .
H10 H 0.5620 0.2776 0.3944 0.081 Uiso 1 1 calc R . .
C25 C 0.1115(3) 0.01800(16) 0.8635(2) 0.0598(8) Uani 1 1 d . . .
H25A H 0.0883 0.0489 0.9107 0.072 Uiso 1 1 calc R . .
H25B H 0.0377 0.0140 0.8136 0.072 Uiso 1 1 calc R . .
C29 C 0.6881(3) 0.1483(2) 0.7351(3) 0.0912(7) Uani 1 1 d U . .
C17 C 0.4338(4) 0.05348(18) 0.3973(2) 0.0690(10) Uani 1 1 d . . .
H17A H 0.4103 0.0117 0.4146 0.083 Uiso 1 1 calc R . .
H17B H 0.5294 0.0555 0.3986 0.083 Uiso 1 1 calc R . .
C1 C 0.0230(3) 0.09169(16) 0.4624(2) 0.0618(8) Uani 1 1 d . . .
H1 H 0.0572 0.0526 0.4771 0.074 Uiso 1 1 calc R . .
C11 C 0.4683(3) 0.28027(17) 0.5181(2) 0.0649(9) Uani 1 1 d . . .
H11 H 0.4838 0.3220 0.5307 0.078 Uiso 1 1 calc R . .
C3 C -0.1181(4) 0.1581(2) 0.3584(3) 0.0784(11) Uani 1 1 d . . .
H3 H -0.1776 0.1632 0.3030 0.094 Uiso 1 1 calc R . .
C4 C -0.0820(3) 0.20816(19) 0.4159(2) 0.0689(10) Uani 1 1 d . . .
H4 H -0.1165 0.2471 0.4006 0.083 Uiso 1 1 calc R . .
C23 C 0.4375(4) 0.04428(17) 0.2155(3) 0.0779(11) Uani 1 1 d . . .
H23 H 0.5155 0.0218 0.2271 0.093 Uiso 1 1 calc R . .
C24 C 0.1343(4) -0.04299(19) 0.9160(3) 0.0850(12) Uani 1 1 d . . .
H24A H 0.1582 -0.0737 0.8697 0.127 Uiso 1 1 calc R . .
H24B H 0.0548 -0.0555 0.9439 0.127 Uiso 1 1 calc R . .
H24C H 0.2044 -0.0387 0.9677 0.127 Uiso 1 1 calc R . .
C2 C -0.0681(4) 0.1008(2) 0.3811(3) 0.0803(11) Uani 1 1 d . . .
H2 H -0.0955 0.0673 0.3416 0.096 Uiso 1 1 calc R . .
C19 C 0.2609(4) 0.09991(19) 0.2740(2) 0.0731(10) Uani 1 1 d . . .
H19 H 0.2177 0.1160 0.3260 0.088 Uiso 1 1 calc R . .
C21 C 0.2714(6) 0.0869(3) 0.1019(3) 0.1039(17) Uani 1 1 d . . .
H21 H 0.2360 0.0937 0.0374 0.125 Uiso 1 1 calc R . .
C30 C 0.6836(3) 0.2115(2) 0.7848(3) 0.0912(7) Uani 1 1 d . . .
H30A H 0.6295 0.2390 0.7432 0.137 Uiso 1 1 calc R . .
H30B H 0.7715 0.2279 0.7953 0.137 Uiso 1 1 calc R . .
H30C H 0.6467 0.2072 0.8472 0.137 Uiso 1 1 calc R . .
C31 C 0.7548(3) 0.1013(2) 0.8036(3) 0.0912(7) Uani 1 1 d . . .
H31A H 0.7152 0.1018 0.8653 0.137 Uiso 1 1 calc R . .
H31B H 0.8471 0.1109 0.8150 0.137 Uiso 1 1 calc R . .
H31C H 0.7446 0.0610 0.7744 0.137 Uiso 1 1 calc R . .
C22 C 0.3850(6) 0.0546(2) 0.1192(3) 0.0994(16) Uani 1 1 d . . .
H22 H 0.4279 0.0393 0.0665 0.119 Uiso 1 1 calc R . .
C20 C 0.2090(5) 0.1095(2) 0.1782(3) 0.0941(13) Uani 1 1 d . . .
H20 H 0.1307 0.1316 0.1659 0.113 Uiso 1 1 calc R . .
C9 C 0.0044(6) 0.30502(19) 0.5752(3) 0.1045(16) Uani 1 1 d . . .
H9A H 0.0219 0.3263 0.5157 0.157 Uiso 1 1 calc R . .
H9B H 0.0498 0.3254 0.6311 0.157 Uiso 1 1 calc R . .
H9C H -0.0890 0.3052 0.5819 0.157 Uiso 1 1 calc R . .
C28 C 0.7501(3) 0.1523(2) 0.6401(3) 0.0912(7) Uani 1 1 d . . .
H28A H 0.7411 0.1134 0.6064 0.137 Uiso 1 1 calc R . .
H28B H 0.8422 0.1622 0.6530 0.137 Uiso 1 1 calc R . .
H28C H 0.7070 0.1840 0.5996 0.137 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
O4 C32 1.207(3) . ?
O3 C32 1.339(3) . ?
O3 C29 1.478(4) . ?
O1 C8 1.218(3) . ?
N1 C32 1.354(3) . ?
N1 C15 1.458(3) . ?
N1 C27 1.489(3) . ?
O2 C16 1.223(3) . ?
C15 C13 1.517(3) . ?
C15 C16 1.535(4) . ?
C15 C7 1.577(3) . ?
C13 C12 1.374(4) . ?
C13 C14 1.389(4) . ?
C14 C33 1.377(4) . ?
C14 N2 1.406(4) . ?
C6 C1 1.370(4) . ?
C6 C5 1.388(4) . ?
C6 C7 1.505(4) . ?
N4 C27 1.457(3) . ?
N4 C7 1.460(3) . ?
N4 H4A 0.8600 . ?
N2 C16 1.354(3) . ?
N2 C17 1.456(4) . ?
C26 C27 1.507(4) . ?
C26 C25 1.519(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C7 C8 1.542(4) . ?
C27 H27 0.9800 . ?
N3 C8 1.353(4) . ?
N3 C5 1.397(4) . ?
N3 C9 1.452(4) . ?
C12 C11 1.394(4) . ?
C12 H12 0.9300 . ?
C5 C4 1.380(4) . ?
C33 C10 1.371(5) . ?
C33 H33 0.9300 . ?
C18 C19 1.369(5) . ?
C18 C23 1.374(4) . ?
C18 C17 1.507(4) . ?
C10 C11 1.375(5) . ?
C10 H10 0.9300 . ?
C25 C24 1.508(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C29 C28 1.485(6) . ?
C29 C31 1.501(6) . ?
C29 C30 1.527(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C1 C2 1.391(5) . ?
C1 H1 0.9300 . ?
C11 H11 0.9300 . ?
C3 C2 1.365(6) . ?
C3 C4 1.367(5) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C23 C22 1.387(6) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C2 H2 0.9300 . ?
C19 C20 1.377(5) . ?
C19 H19 0.9300 . ?
C21 C20 1.351(7) . ?
C21 C22 1.351(7) . ?
C21 H21 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C22 H22 0.9300 . ?
C20 H20 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C32 O3 C29 121.5(3) . . ?
C32 N1 C15 127.3(2) . . ?
C32 N1 C27 120.4(2) . . ?
C15 N1 C27 112.28(19) . . ?
N1 C15 C13 119.5(2) . . ?
N1 C15 C16 110.6(2) . . ?
C13 C15 C16 102.1(2) . . ?
N1 C15 C7 99.74(18) . . ?
C13 C15 C7 115.1(2) . . ?
C16 C15 C7 109.8(2) . . ?
C12 C13 C14 119.6(2) . . ?
C12 C13 C15 132.4(2) . . ?
C14 C13 C15 108.0(2) . . ?
C33 C14 C13 122.4(3) . . ?
C33 C14 N2 127.4(3) . . ?
C13 C14 N2 110.1(2) . . ?
C1 C6 C5 119.6(3) . . ?
C1 C6 C7 131.7(3) . . ?
C5 C6 C7 108.5(2) . . ?
C27 N4 C7 107.40(19) . . ?
C27 N4 H4A 126.3 . . ?
C7 N4 H4A 126.3 . . ?
C16 N2 C14 111.2(2) . . ?
C16 N2 C17 123.9(3) . . ?
C14 N2 C17 124.6(3) . . ?
O4 C32 O3 126.3(2) . . ?
O4 C32 N1 123.1(2) . . ?
O3 C32 N1 110.5(2) . . ?
C27 C26 C25 114.4(2) . . ?
C27 C26 H26A 108.7 . . ?
C25 C26 H26A 108.7 . . ?
C27 C26 H26B 108.7 . . ?
C25 C26 H26B 108.7 . . ?
H26A C26 H26B 107.6 . . ?
O2 C16 N2 126.3(3) . . ?
O2 C16 C15 125.4(2) . . ?
N2 C16 C15 108.4(2) . . ?
N4 C7 C6 113.9(2) . . ?
N4 C7 C8 109.7(2) . . ?
C6 C7 C8 101.9(2) . . ?
N4 C7 C15 104.0(2) . . ?
C6 C7 C15 117.9(2) . . ?
C8 C7 C15 109.5(2) . . ?
N4 C27 N1 103.93(19) . . ?
N4 C27 C26 110.8(2) . . ?
N1 C27 C26 113.3(2) . . ?
N4 C27 H27 109.5 . . ?
N1 C27 H27 109.5 . . ?
C26 C27 H27 109.5 . . ?
C8 N3 C5 111.5(2) . . ?
C8 N3 C9 123.0(3) . . ?
C5 N3 C9 124.7(3) . . ?
C13 C12 C11 118.2(3) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 N3 128.4(3) . . ?
C6 C5 N3 109.8(2) . . ?
O1 C8 N3 125.8(3) . . ?
O1 C8 C7 126.3(3) . . ?
N3 C8 C7 107.9(2) . . ?
C10 C33 C14 117.4(3) . . ?
C10 C33 H33 121.3 . . ?
C14 C33 H33 121.3 . . ?
C19 C18 C23 118.3(3) . . ?
C19 C18 C17 122.9(3) . . ?
C23 C18 C17 118.8(3) . . ?
C33 C10 C11 121.3(3) . . ?
C33 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C24 C25 C26 112.1(3) . . ?
C24 C25 H25A 109.2 . . ?
C26 C25 H25A 109.2 . . ?
C24 C25 H25B 109.2 . . ?
C26 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
O3 C29 C28 102.3(3) . . ?
O3 C29 C31 110.9(3) . . ?
C28 C29 C31 112.1(4) . . ?
O3 C29 C30 108.6(3) . . ?
C28 C29 C30 111.3(4) . . ?
C31 C29 C30 111.2(4) . . ?
N2 C17 C18 114.0(2) . . ?
N2 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
N2 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C6 C1 C2 118.6(3) . . ?
C6 C1 H1 120.7 . . ?
C2 C1 H1 120.7 . . ?
C10 C11 C12 121.0(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 118.1(3) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C18 C23 C22 120.4(4) . . ?
C18 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C3 C2 C1 121.1(4) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C18 C19 C20 120.8(4) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C20 C21 C22 120.2(4) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C21 C22 C23 120.0(4) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C21 C20 C19 120.3(5) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C29 C28 H28A 109.5 . . ?
C29 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C29 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
C32 N1 C15 C13 -31.5(4) . . . . ?
C27 N1 C15 C13 146.1(2) . . . . ?
C32 N1 C15 C16 86.6(3) . . . . ?
C27 N1 C15 C16 -95.8(2) . . . . ?
C32 N1 C15 C7 -157.8(3) . . . . ?
C27 N1 C15 C7 19.8(3) . . . . ?
N1 C15 C13 C12 -55.2(4) . . . . ?
C16 C15 C13 C12 -177.6(3) . . . . ?
C7 C15 C13 C12 63.5(4) . . . . ?
N1 C15 C13 C14 125.8(2) . . . . ?
C16 C15 C13 C14 3.4(3) . . . . ?
C7 C15 C13 C14 -115.5(2) . . . . ?
C12 C13 C14 C33 0.3(4) . . . . ?
C15 C13 C14 C33 179.4(2) . . . . ?
C12 C13 C14 N2 178.8(2) . . . . ?
C15 C13 C14 N2 -2.0(3) . . . . ?
C33 C14 N2 C16 178.0(3) . . . . ?
C13 C14 N2 C16 -0.4(3) . . . . ?
C33 C14 N2 C17 3.3(4) . . . . ?
C13 C14 N2 C17 -175.2(3) . . . . ?
C29 O3 C32 O4 -16.3(5) . . . . ?
C29 O3 C32 N1 166.3(3) . . . . ?
C15 N1 C32 O4 166.4(3) . . . . ?
C27 N1 C32 O4 -11.0(4) . . . . ?
C15 N1 C32 O3 -16.1(4) . . . . ?
C27 N1 C32 O3 166.5(2) . . . . ?
C14 N2 C16 O2 -177.5(3) . . . . ?
C17 N2 C16 O2 -2.8(4) . . . . ?
C14 N2 C16 C15 2.7(3) . . . . ?
C17 N2 C16 C15 177.4(2) . . . . ?
N1 C15 C16 O2 48.3(3) . . . . ?
C13 C15 C16 O2 176.6(3) . . . . ?
C7 C15 C16 O2 -60.8(3) . . . . ?
N1 C15 C16 N2 -131.9(2) . . . . ?
C13 C15 C16 N2 -3.7(3) . . . . ?
C7 C15 C16 N2 118.9(2) . . . . ?
C27 N4 C7 C6 165.0(2) . . . . ?
C27 N4 C7 C8 -81.5(3) . . . . ?
C27 N4 C7 C15 35.5(3) . . . . ?
C1 C6 C7 N4 -52.1(4) . . . . ?
C5 C6 C7 N4 122.0(2) . . . . ?
C1 C6 C7 C8 -170.1(3) . . . . ?
C5 C6 C7 C8 4.0(3) . . . . ?
C1 C6 C7 C15 70.1(4) . . . . ?
C5 C6 C7 C15 -115.7(3) . . . . ?
N1 C15 C7 N4 -32.8(2) . . . . ?
C13 C15 C7 N4 -162.0(2) . . . . ?
C16 C15 C7 N4 83.4(2) . . . . ?
N1 C15 C7 C6 -160.0(2) . . . . ?
C13 C15 C7 C6 70.8(3) . . . . ?
C16 C15 C7 C6 -43.8(3) . . . . ?
N1 C15 C7 C8 84.3(2) . . . . ?
C13 C15 C7 C8 -44.9(3) . . . . ?
C16 C15 C7 C8 -159.5(2) . . . . ?
C7 N4 C27 N1 -22.9(3) . . . . ?
C7 N4 C27 C26 -144.9(2) . . . . ?
C32 N1 C27 N4 178.2(2) . . . . ?
C15 N1 C27 N4 0.4(3) . . . . ?
C32 N1 C27 C26 -61.4(3) . . . . ?
C15 N1 C27 C26 120.8(2) . . . . ?
C25 C26 C27 N4 -59.9(3) . . . . ?
C25 C26 C27 N1 -176.3(2) . . . . ?
C14 C13 C12 C11 0.8(4) . . . . ?
C15 C13 C12 C11 -178.1(3) . . . . ?
C1 C6 C5 C4 -1.9(4) . . . . ?
C7 C6 C5 C4 -176.9(3) . . . . ?
C1 C6 C5 N3 174.6(3) . . . . ?
C7 C6 C5 N3 -0.4(3) . . . . ?
C8 N3 C5 C4 172.0(3) . . . . ?
C9 N3 C5 C4 2.0(5) . . . . ?
C8 N3 C5 C6 -4.2(3) . . . . ?
C9 N3 C5 C6 -174.2(3) . . . . ?
C5 N3 C8 O1 -173.2(3) . . . . ?
C9 N3 C8 O1 -3.0(5) . . . . ?
C5 N3 C8 C7 6.8(3) . . . . ?
C9 N3 C8 C7 177.0(3) . . . . ?
N4 C7 C8 O1 52.5(3) . . . . ?
C6 C7 C8 O1 173.5(3) . . . . ?
C15 C7 C8 O1 -61.0(3) . . . . ?
N4 C7 C8 N3 -127.5(2) . . . . ?
C6 C7 C8 N3 -6.5(3) . . . . ?
C15 C7 C8 N3 119.0(2) . . . . ?
C13 C14 C33 C10 -1.1(4) . . . . ?
N2 C14 C33 C10 -179.3(3) . . . . ?
C14 C33 C10 C11 0.8(5) . . . . ?
C27 C26 C25 C24 -174.7(3) . . . . ?
C32 O3 C29 C28 -173.8(3) . . . . ?
C32 O3 C29 C31 66.5(5) . . . . ?
C32 O3 C29 C30 -56.0(4) . . . . ?
C16 N2 C17 C18 118.6(3) . . . . ?
C14 N2 C17 C18 -67.3(4) . . . . ?
C19 C18 C17 N2 -21.6(5) . . . . ?
C23 C18 C17 N2 159.8(3) . . . . ?
C5 C6 C1 C2 1.0(4) . . . . ?
C7 C6 C1 C2 174.6(3) . . . . ?
C33 C10 C11 C12 0.2(5) . . . . ?
C13 C12 C11 C10 -1.1(5) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C6 C5 C4 C3 1.2(5) . . . . ?
N3 C5 C4 C3 -174.6(3) . . . . ?
C19 C18 C23 C22 -0.1(6) . . . . ?
C17 C18 C23 C22 178.6(4) . . . . ?
C4 C3 C2 C1 -1.2(6) . . . . ?
C6 C1 C2 C3 0.5(5) . . . . ?
C23 C18 C19 C20 0.6(6) . . . . ?
C17 C18 C19 C20 -178.0(4) . . . . ?
C20 C21 C22 C23 0.3(7) . . . . ?
C18 C23 C22 C21 -0.3(7) . . . . ?
C22 C21 C20 C19 0.2(7) . . . . ?
C18 C19 C20 C21 -0.7(7) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.889
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.049
