# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_SSB_ST_TMNapBDo
_database_code_depnum_ccdc_archive 'CCDC 995716'
_audit_update_record             
;
2014-04-07 deposited with the CCDC.
2016-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        triazolyl
_chemical_name_common            triazolyl
_chemical_formula_moiety         ' C18 H19 N3 O4 '
_chemical_formula_sum            'C18 H19 N3 O4'
_chemical_compound_source        synthesis
_chemical_melting_point          ?

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         341.36

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_int_tables_number      4
_chemical_absolute_configuration syn
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.8080(7)
_cell_length_b                   29.856(4)
_cell_length_c                   9.5397(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.185(7)
_cell_angle_gamma                90.00
_cell_volume                     1654.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3068
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      25.5
_exptl_crystal_size_max          .20
_exptl_crystal_size_mid          .10
_exptl_crystal_size_min          .10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5214
_exptl_absorpt_correction_T_max  0.8245
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_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            17451
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0653
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         26.77
_reflns_number_total             4410
_reflns_number_gt                2923
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.0506P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0171(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.8(14)
_refine_ls_number_reflns         4410
_refine_ls_number_parameters     459
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_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 0.8339(6) 1.20763(10) 0.7665(4) 0.0782(9) Uani 1 1 d . . .
O5 O 0.4395(6) 0.87252(12) 0.1467(3) 0.0862(11) Uani 1 1 d . . .
O6 O 0.9525(6) 0.85795(17) 0.0090(5) 0.152(2) Uani 1 1 d . . .
H6 H 0.9671 0.8783 0.0659 0.228 Uiso 1 1 calc R . .
C35 C 0.4299(11) 0.79558(17) 0.0740(6) 0.1062(19) Uani 1 1 d . . .
H35A H 0.5270 0.7693 0.0661 0.127 Uiso 1 1 calc R . .
H35B H 0.3277 0.7911 0.1529 0.127 Uiso 1 1 calc R . .
N3 N 0.6384(6) 0.94126(12) 0.1545(4) 0.0675(11) Uani 1 1 d . . .
N2 N 0.8658(7) 0.93333(15) 0.1683(5) 0.0873(13) Uani 1 1 d . . .
N1 N 0.9518(7) 0.96495(14) 0.2503(5) 0.0825(12) Uani 1 1 d . . .
C21 C 0.7232(7) 1.10354(14) 0.4805(4) 0.0522(11) Uani 1 1 d . . .
C28 C 0.7805(8) 0.99297(15) 0.2887(5) 0.0607(12) Uani 1 1 d . . .
C20 C 0.9301(7) 1.10448(15) 0.5585(4) 0.0525(11) Uani 1 1 d . . .
C18 C 0.8167(8) 1.17267(16) 0.6715(5) 0.0630(13) Uani 1 1 d . . .
C23 C 0.6110(7) 1.17328(16) 0.5930(5) 0.0656(13) Uani 1 1 d . . .
H23 H 0.5064 1.1966 0.6045 0.079 Uiso 1 1 calc R . .
C26 C 0.8262(7) 1.03175(15) 0.3783(4) 0.0570(12) Uani 1 1 d . . .
C27 C 0.6757(7) 1.06720(15) 0.3917(4) 0.0572(12) Uani 1 1 d . . .
H27 H 0.5391 1.0670 0.3405 0.069 Uiso 1 1 calc R . .
C25 C 1.0354(7) 1.03366(15) 0.4543(5) 0.0599(12) Uani 1 1 d . . .
H25 H 1.1412 1.0105 0.4447 0.072 Uiso 1 1 calc R . .
C19 C 0.9759(7) 1.13953(15) 0.6551(5) 0.0603(12) Uani 1 1 d . . .
H19 H 1.1123 1.1399 0.7065 0.072 Uiso 1 1 calc R . .
C24 C 1.0861(7) 1.06841(17) 0.5408(4) 0.0599(12) Uani 1 1 d . . .
H24 H 1.2254 1.0686 0.5892 0.072 Uiso 1 1 calc R . .
C22 C 0.5656(7) 1.13966(16) 0.5001(5) 0.0652(13) Uani 1 1 d . . .
H22 H 0.4294 1.1403 0.4486 0.078 Uiso 1 1 calc R . .
C30 C 0.4892(8) 0.91038(16) 0.0725(6) 0.0733(13) Uani 1 1 d . . .
H30 H 0.3448 0.9258 0.0501 0.088 Uiso 1 1 calc R . .
C29 C 0.5802(8) 0.97828(16) 0.2280(5) 0.0702(13) Uani 1 1 d . . .
H29 H 0.4348 0.9911 0.2356 0.084 Uiso 1 1 calc R . .
C33 C 0.5792(9) 0.83568(17) 0.1025(5) 0.0777(14) Uani 1 1 d . . .
H33 H 0.6872 0.8282 0.1781 0.093 Uiso 1 1 calc R . .
C31 C 0.5950(9) 0.8948(2) -0.0595(5) 0.0962(18) Uani 1 1 d . . .
H31A H 0.7039 0.9168 -0.0944 0.115 Uiso 1 1 calc R . .
H31B H 0.4781 0.8897 -0.1306 0.115 Uiso 1 1 calc R . .
C32 C 0.7150(8) 0.8519(2) -0.0230(6) 0.0872(17) Uani 1 1 d . . .
H32 H 0.6984 0.8306 -0.1004 0.105 Uiso 1 1 calc R . .
C17 C 1.0430(8) 1.21157(19) 0.8461(6) 0.0996(18) Uani 1 1 d . . .
H17A H 1.0667 1.1847 0.8997 0.149 Uiso 1 1 calc R . .
H17B H 1.0319 1.2367 0.9084 0.149 Uiso 1 1 calc R . .
H17C H 1.1702 1.2159 0.7836 0.149 Uiso 1 1 calc R . .
O8 O 0.2990(6) 0.79973(12) -0.0474(3) 0.0886(10) Uani 1 1 d . . .
H8A H 0.1897 0.8164 -0.0326 0.133 Uiso 1 1 calc R . .
O1 O 0.3579(6) 1.16963(11) 1.1788(3) 0.0753(9) Uani 1 1 d . . .
O2 O -0.0673(5) 0.83465(11) 0.6316(3) 0.0702(9) Uani 1 1 d . . .
O3 O 0.4418(5) 0.81032(12) 0.4830(4) 0.0992(12) Uani 1 1 d . . .
H3 H 0.4628 0.8358 0.5122 0.149 Uiso 1 1 calc R . .
N4 N 0.1379(6) 0.90112(12) 0.5819(3) 0.0565(9) Uani 1 1 d . . .
N6 N 0.4594(6) 0.93371(12) 0.6262(4) 0.0607(10) Uani 1 1 d . . .
N5 N 0.3664(6) 0.89946(13) 0.5581(4) 0.0650(10) Uani 1 1 d . . .
C5 C 0.2392(7) 1.05123(13) 0.9575(4) 0.0486(11) Uani 1 1 d . . .
C10 C 0.5497(7) 1.02058(15) 0.7549(4) 0.0547(11) Uani 1 1 d . . .
H10 H 0.6540 1.0104 0.6883 0.066 Uiso 1 1 calc R . .
C4 C 0.4443(7) 1.07522(14) 0.9312(4) 0.0502(11) Uani 1 1 d . . .
C11 C 0.5975(7) 1.05873(14) 0.8292(4) 0.0555(11) Uani 1 1 d . . .
H11 H 0.7339 1.0741 0.8120 0.067 Uiso 1 1 calc R . .
C8 C 0.1959(7) 1.01195(14) 0.8797(4) 0.0520(11) Uani 1 1 d . . .
H8 H 0.0622 0.9958 0.8977 0.062 Uiso 1 1 calc R . .
C3 C 0.4884(8) 1.11561(15) 1.0060(5) 0.0591(12) Uani 1 1 d . . .
H3A H 0.6221 1.1317 0.9878 0.071 Uiso 1 1 calc R . .
C12 C 0.2914(7) 0.95628(15) 0.6935(4) 0.0500(10) Uani 1 1 d . . .
C2 C 0.3386(8) 1.13090(15) 1.1031(5) 0.0561(12) Uani 1 1 d . . .
C13 C -0.0214(7) 0.86624(15) 0.5281(4) 0.0587(12) Uani 1 1 d . . .
H13 H -0.1662 0.8805 0.4999 0.070 Uiso 1 1 calc R . .
C9 C 0.3442(7) 0.99654(13) 0.7780(4) 0.0470(10) Uani 1 1 d . . .
C7 C 0.1343(8) 1.10647(15) 1.1320(5) 0.0645(12) Uani 1 1 d . . .
H7 H 0.0323 1.1167 1.1997 0.077 Uiso 1 1 calc R . .
C6 C 0.0874(7) 1.06790(15) 1.0602(4) 0.0584(12) Uani 1 1 d . . .
H6A H -0.0474 1.0523 1.0795 0.070 Uiso 1 1 calc R . .
C14 C 0.0709(8) 0.84089(16) 0.4079(4) 0.0685(13) Uani 1 1 d . . .
H14A H 0.1741 0.8594 0.3530 0.082 Uiso 1 1 calc R . .
H14B H -0.0528 0.8304 0.3479 0.082 Uiso 1 1 calc R . .
C1 C 0.5646(9) 1.19479(16) 1.1636(6) 0.0931(16) Uani 1 1 d . . .
H1A H 0.6943 1.1762 1.1865 0.140 Uiso 1 1 calc R . .
H1B H 0.5611 1.2201 1.2255 0.140 Uiso 1 1 calc R . .
H1C H 0.5778 1.2050 1.0685 0.140 Uiso 1 1 calc R . .
C16 C 0.0833(8) 0.79623(17) 0.6145(5) 0.0719(13) Uani 1 1 d . . .
H16 H 0.2004 0.7963 0.6886 0.086 Uiso 1 1 calc R . .
C15 C 0.1994(7) 0.80181(17) 0.4725(5) 0.0722(13) Uani 1 1 d . . .
H15 H 0.1735 0.7749 0.4158 0.087 Uiso 1 1 calc R . .
C34 C 0.0875(7) 0.93580(14) 0.6662(5) 0.0562(11) Uani 1 1 d . . .
H34 H -0.0571 0.9441 0.6990 0.067 Uiso 1 1 calc R . .
C36 C -0.0608(10) 0.75507(18) 0.6271(6) 0.1021(19) Uani 1 1 d . . .
H36A H 0.0392 0.7291 0.6336 0.123 Uiso 1 1 calc R . .
H36B H -0.1497 0.7567 0.7129 0.123 Uiso 1 1 calc R . .
O9 O -0.2116(6) 0.74944(12) 0.5132(5) 0.1039(13) Uani 1 1 d . . .
H9 H -0.3226 0.7661 0.5224 0.156 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C18 1.385(5) . ?
O4 C17 1.435(5) . ?
O5 C30 1.365(5) . ?
O5 C33 1.431(6) . ?
O6 C32 1.423(5) . ?
C35 O8 1.389(5) . ?
C35 C33 1.503(7) . ?
N3 N2 1.347(5) . ?
N3 C29 1.352(5) . ?
N3 C30 1.486(6) . ?
N2 N1 1.323(5) . ?
N1 C28 1.352(5) . ?
C21 C27 1.404(6) . ?
C21 C20 1.411(5) . ?
C21 C22 1.427(6) . ?
C28 C29 1.370(6) . ?
C28 C26 1.463(6) . ?
C20 C24 1.418(6) . ?
C20 C19 1.420(6) . ?
C18 C19 1.364(6) . ?
C18 C23 1.408(6) . ?
C23 C22 1.364(6) . ?
C26 C27 1.379(5) . ?
C26 C25 1.414(6) . ?
C25 C24 1.357(6) . ?
C30 C31 1.478(6) . ?
C33 C32 1.516(7) . ?
C31 C32 1.498(7) . ?
O1 C2 1.368(5) . ?
O1 C1 1.424(5) . ?
O2 C13 1.392(5) . ?
O2 C16 1.452(5) . ?
O3 C15 1.434(5) . ?
N4 C34 1.344(5) . ?
N4 N5 1.348(4) . ?
N4 C13 1.483(5) . ?
N6 N5 1.326(4) . ?
N6 C12 1.350(5) . ?
C5 C8 1.410(5) . ?
C5 C6 1.411(5) . ?
C5 C4 1.413(5) . ?
C10 C11 1.370(5) . ?
C10 C9 1.411(5) . ?
C4 C11 1.409(5) . ?
C4 C3 1.424(6) . ?
C8 C9 1.379(5) . ?
C3 C2 1.352(6) . ?
C12 C34 1.358(5) . ?
C12 C9 1.479(5) . ?
C2 C7 1.421(6) . ?
C13 C14 1.476(5) . ?
C7 C6 1.366(5) . ?
C14 C15 1.515(6) . ?
C16 C36 1.492(6) . ?
C16 C15 1.524(6) . ?
C36 O9 1.403(6) . ?

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
C18 O4 C17 117.9(4) . . ?
C30 O5 C33 111.3(3) . . ?
O8 C35 C33 113.2(4) . . ?
N2 N3 C29 109.9(4) . . ?
N2 N3 C30 120.8(4) . . ?
C29 N3 C30 129.3(4) . . ?
N1 N2 N3 107.5(4) . . ?
N2 N1 C28 109.0(4) . . ?
C27 C21 C20 119.9(4) . . ?
C27 C21 C22 122.6(4) . . ?
C20 C21 C22 117.5(4) . . ?
N1 C28 C29 108.2(4) . . ?
N1 C28 C26 121.1(4) . . ?
C29 C28 C26 130.7(4) . . ?
C21 C20 C24 117.8(4) . . ?
C21 C20 C19 121.0(4) . . ?
C24 C20 C19 121.2(4) . . ?
C19 C18 O4 125.0(4) . . ?
C19 C18 C23 121.5(5) . . ?
O4 C18 C23 113.4(4) . . ?
C22 C23 C18 119.9(4) . . ?
C27 C26 C25 117.8(4) . . ?
C27 C26 C28 123.2(4) . . ?
C25 C26 C28 119.0(4) . . ?
C26 C27 C21 121.7(4) . . ?
C24 C25 C26 121.8(4) . . ?
C18 C19 C20 118.9(4) . . ?
C25 C24 C20 121.0(4) . . ?
C23 C22 C21 121.2(4) . . ?
O5 C30 C31 105.7(4) . . ?
O5 C30 N3 111.4(4) . . ?
C31 C30 N3 113.6(4) . . ?
N3 C29 C28 105.5(4) . . ?
O5 C33 C35 109.8(4) . . ?
O5 C33 C32 106.5(4) . . ?
C35 C33 C32 114.4(5) . . ?
C30 C31 C32 105.3(4) . . ?
O6 C32 C31 113.1(5) . . ?
O6 C32 C33 112.2(5) . . ?
C31 C32 C33 102.4(4) . . ?
C2 O1 C1 117.4(4) . . ?
C13 O2 C16 109.8(3) . . ?
C34 N4 N5 110.2(3) . . ?
C34 N4 C13 127.7(3) . . ?
N5 N4 C13 121.9(4) . . ?
N5 N6 C12 108.9(3) . . ?
N6 N5 N4 106.8(3) . . ?
C8 C5 C6 123.2(4) . . ?
C8 C5 C4 118.5(4) . . ?
C6 C5 C4 118.2(4) . . ?
C11 C10 C9 120.8(4) . . ?
C11 C4 C5 118.7(4) . . ?
C11 C4 C3 121.9(4) . . ?
C5 C4 C3 119.4(4) . . ?
C10 C11 C4 121.4(4) . . ?
C9 C8 C5 122.5(4) . . ?
C2 C3 C4 120.9(4) . . ?
N6 C12 C34 108.4(4) . . ?
N6 C12 C9 121.1(4) . . ?
C34 C12 C9 130.6(4) . . ?
C3 C2 O1 126.5(4) . . ?
C3 C2 C7 119.9(4) . . ?
O1 C2 C7 113.5(4) . . ?
O2 C13 C14 105.9(4) . . ?
O2 C13 N4 110.5(3) . . ?
C14 C13 N4 113.6(4) . . ?
C8 C9 C10 118.1(4) . . ?
C8 C9 C12 121.7(4) . . ?
C10 C9 C12 120.2(4) . . ?
C6 C7 C2 120.0(4) . . ?
C7 C6 C5 121.4(4) . . ?
C13 C14 C15 105.0(3) . . ?
O2 C16 C36 107.7(4) . . ?
O2 C16 C15 106.4(4) . . ?
C36 C16 C15 114.3(5) . . ?
O3 C15 C14 112.0(4) . . ?
O3 C15 C16 113.2(4) . . ?
C14 C15 C16 103.1(4) . . ?
N4 C34 C12 105.7(4) . . ?
O9 C36 C16 112.7(4) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.77
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_SSB_ST_TNBBAc
_database_code_depnum_ccdc_archive 'CCDC 995717'
_audit_update_record             
;
2014-04-07 deposited with the CCDC.
2016-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        triazolyl
_chemical_name_common            triazolyl
_chemical_formula_moiety         ' C13 H14 N4 O5 '
_chemical_formula_sum            'C13 H14 N4 O5'
_exptl_crystal_recrystallization_method 'slow evaporation'
_chemical_melting_point          ?

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         306.28

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   'P 21 21 21'
_symmetry_int_tables_number      19
_chemical_absolute_configuration syn

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'

_cell_length_a                   6.4456(7)
_cell_length_b                   9.8102(8)
_cell_length_c                   21.8210(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1379.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_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            15090
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_sigmaI/netI    0.0977
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         28.40
_reflns_number_total             3180
_reflns_number_gt                1701
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.0442P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0156(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3.0(15)
_refine_ls_number_reflns         3180
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.933
_refine_ls_shift/su_max          0.001
_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
N3 N 0.5892(4) 0.60661(19) 0.93091(9) 0.0477(6) Uani 1 1 d . . .
N2 N 0.4329(4) 0.64284(19) 0.89546(9) 0.0473(6) Uani 1 1 d . . .
N4 N 0.5652(4) 0.47366(18) 0.94237(9) 0.0379(6) Uani 1 1 d . . .
N1 N -0.4244(4) 0.5669(3) 0.73973(10) 0.0517(7) Uani 1 1 d . . .
O3 O 0.6003(3) 0.34078(14) 1.03178(7) 0.0405(5) Uani 1 1 d . . .
O5 O 0.8978(3) 0.57269(15) 1.11577(8) 0.0483(5) Uani 1 1 d . . .
H5 H 0.9223 0.6546 1.1176 0.072 Uiso 1 1 calc R . .
O1 O -0.4456(4) 0.6695(2) 0.70734(9) 0.0718(7) Uani 1 1 d . . .
O2 O -0.5490(4) 0.4741(2) 0.74188(9) 0.0650(6) Uani 1 1 d . . .
C13 C 0.3986(5) 0.4836(3) 1.09975(14) 0.0552(8) Uani 1 1 d . . .
H13A H 0.4070 0.5475 1.1336 0.066 Uiso 1 1 calc R . .
H13B H 0.3367 0.5300 1.0650 0.066 Uiso 1 1 calc R . .
C11 C 0.7653(4) 0.5462(2) 1.06528(11) 0.0378(6) Uani 1 1 d . . .
H11 H 0.6903 0.6292 1.0538 0.045 Uiso 1 1 calc R . .
C8 C 0.3946(5) 0.4257(2) 0.91436(11) 0.0432(7) Uani 1 1 d . . .
H8 H 0.3452 0.3367 0.9153 0.052 Uiso 1 1 calc R . .
C4 C 0.1207(4) 0.5424(2) 0.84661(11) 0.0398(6) Uani 1 1 d . . .
C12 C 0.6114(4) 0.4340(2) 1.08328(11) 0.0374(6) Uani 1 1 d . . .
H12 H 0.6682 0.3846 1.1185 0.045 Uiso 1 1 calc R . .
C5 C -0.0099(4) 0.4309(3) 0.84052(11) 0.0429(7) Uani 1 1 d . . .
H5A H 0.0235 0.3503 0.8606 0.051 Uiso 1 1 calc R . .
C2 C -0.1080(5) 0.6699(3) 0.78125(13) 0.0515(8) Uani 1 1 d . . .
H2 H -0.1429 0.7506 0.7614 0.062 Uiso 1 1 calc R . .
C3 C 0.0704(5) 0.6621(3) 0.81621(12) 0.0513(8) Uani 1 1 d . . .
H3 H 0.1573 0.7375 0.8194 0.062 Uiso 1 1 calc R . .
C9 C 0.7125(4) 0.3968(2) 0.98189(11) 0.0414(7) Uani 1 1 d . . .
H9 H 0.7784 0.3237 0.9582 0.050 Uiso 1 1 calc R . .
C7 C 0.3083(4) 0.5334(2) 0.88426(11) 0.0377(7) Uani 1 1 d . . .
C6 C -0.1882(5) 0.4361(3) 0.80541(11) 0.0444(7) Uani 1 1 d . . .
H6 H -0.2748 0.3607 0.8016 0.053 Uiso 1 1 calc R . .
C1 C -0.2329(5) 0.5572(3) 0.77623(12) 0.0434(7) Uani 1 1 d . . .
C10 C 0.8755(4) 0.4873(2) 1.00970(11) 0.0420(7) Uani 1 1 d . . .
H10A H 0.9170 0.5586 0.9814 0.050 Uiso 1 1 calc R . .
H10B H 0.9969 0.4354 1.0217 0.050 Uiso 1 1 calc R . .
O4 O 0.2757(4) 0.37058(17) 1.11658(9) 0.0649(6) Uani 1 1 d . . .
H4 H 0.1710 0.3973 1.1342 0.097 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
N3 N2 1.319(3) . ?
N3 N4 1.337(2) . ?
N2 C7 1.363(3) . ?
N4 C8 1.343(3) . ?
N4 C9 1.488(3) . ?
N1 O2 1.215(3) . ?
N1 O1 1.237(3) . ?
N1 C1 1.472(4) . ?
O3 C9 1.418(3) . ?
O3 C12 1.451(3) . ?
O5 C11 1.418(3) . ?
C13 O4 1.411(3) . ?
C13 C12 1.499(4) . ?
C11 C10 1.519(3) . ?
C11 C12 1.533(3) . ?
C8 C7 1.363(3) . ?
C4 C3 1.387(3) . ?
C4 C5 1.386(3) . ?
C4 C7 1.465(4) . ?
C5 C6 1.382(4) . ?
C2 C1 1.372(4) . ?
C2 C3 1.382(4) . ?
C9 C10 1.503(3) . ?
C6 C1 1.379(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N3 N4 106.5(2) . . ?
N3 N2 C7 110.07(19) . . ?
N3 N4 C8 110.6(2) . . ?
N3 N4 C9 121.9(2) . . ?
C8 N4 C9 127.5(2) . . ?
O2 N1 O1 123.9(3) . . ?
O2 N1 C1 119.0(2) . . ?
O1 N1 C1 117.0(3) . . ?
C9 O3 C12 108.98(16) . . ?
O4 C13 C12 108.7(2) . . ?
O5 C11 C10 114.1(2) . . ?
O5 C11 C12 108.8(2) . . ?
C10 C11 C12 103.55(18) . . ?
N4 C8 C7 106.4(2) . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 C7 120.8(2) . . ?
C5 C4 C7 120.5(2) . . ?
O3 C12 C13 110.2(2) . . ?
O3 C12 C11 106.62(19) . . ?
C13 C12 C11 114.88(19) . . ?
C6 C5 C4 121.9(2) . . ?
C1 C2 C3 119.2(2) . . ?
C2 C3 C4 120.4(3) . . ?
O3 C9 N4 108.4(2) . . ?
O3 C9 C10 105.99(19) . . ?
N4 C9 C10 112.4(2) . . ?
N2 C7 C8 106.5(2) . . ?
N2 C7 C4 122.7(2) . . ?
C8 C7 C4 130.9(2) . . ?
C1 C6 C5 117.5(3) . . ?
C2 C1 C6 122.3(3) . . ?
C2 C1 N1 118.9(2) . . ?
C6 C1 N1 118.7(3) . . ?
C9 C10 C11 102.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        28.40
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.045

