# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_abd204_0m
_database_code_depnum_ccdc_archive 'CCDC 890798'
_audit_update_record             
;
2012-07-06 deposited with the CCDC.	2020-11-24 downloaded from the CCDC.
;
#TrackingRef 'EuPyboxPh.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 Eu N6 O12'
_chemical_formula_weight         649.33

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'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.1845(2)
_cell_length_b                   10.3327(2)
_cell_length_c                   11.9654(2)
_cell_angle_alpha                98.419(1)
_cell_angle_beta                 108.109(1)
_cell_angle_gamma                91.791(1)
_cell_volume                     1064.08(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9889
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      30.54

_exptl_crystal_description       plate
_exptl_crystal_colour            clear
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.027
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    3.029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2325
_exptl_absorpt_correction_T_max  0.7722
_exptl_absorpt_process_details   'Bruker SADABS (Bruker 2005)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD'
_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            22516
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3740
_reflns_number_gt                3492
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker, 2001)'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 2001)'

_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)+(0.0235P)²+1.3510P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3740
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0208
_refine_ls_wR_factor_ref         0.0525
_refine_ls_wR_factor_gt          0.0502
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.002
_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
Eu1 Eu -0.155458(17) 0.696373(15) 0.197174(13) 0.01237(6) Uani 1 1 d . . .
O1 O 0.3538(2) 0.6437(2) 0.4089(2) 0.0181(5) Uani 1 1 d . . .
O2 O -0.0821(3) 1.1133(2) 0.1073(2) 0.0252(6) Uani 1 1 d . . .
O3 O -0.1551(3) 0.4609(2) 0.1291(2) 0.0191(5) Uani 1 1 d . . .
H3A H -0.090(6) 0.434(4) 0.122(4) 0.037(16) Uiso 1 1 d . . .
H3B H -0.228(6) 0.436(5) 0.069(5) 0.059(17) Uiso 1 1 d . . .
O4 O -0.0227(2) 0.6679(2) 0.04112(19) 0.0186(5) Uani 1 1 d . . .
O5 O -0.2707(2) 0.6714(2) -0.0252(2) 0.0184(5) Uani 1 1 d . . .
O6 O -0.1418(3) 0.6308(2) -0.1496(2) 0.0229(5) Uani 1 1 d . . .
O7 O -0.4172(2) 0.7715(2) 0.1793(2) 0.0192(5) Uani 1 1 d . . .
O8 O -0.6348(2) 0.6503(2) 0.1067(2) 0.0219(5) Uani 1 1 d . . .
O9 O -0.4161(2) 0.5625(2) 0.1303(2) 0.0189(5) Uani 1 1 d . . .
O10 O -0.1245(3) 0.8319(2) 0.3911(2) 0.0185(5) Uani 1 1 d . . .
O11 O -0.1943(3) 0.7674(3) 0.5335(2) 0.0330(6) Uani 1 1 d . . .
O12 O -0.2103(3) 0.6299(2) 0.3726(2) 0.0192(5) Uani 1 1 d . . .
N1 N 0.0954(3) 0.8551(3) 0.2534(2) 0.0157(6) Uani 1 1 d . . .
N2 N 0.0956(3) 0.6221(3) 0.3247(2) 0.0155(6) Uani 1 1 d . . .
N3 N -0.1802(3) 0.9217(3) 0.1335(2) 0.0166(6) Uani 1 1 d . . .
N4 N -0.1455(3) 0.6558(3) -0.0467(2) 0.0166(6) Uani 1 1 d . . .
N5 N -0.4933(3) 0.6598(3) 0.1376(2) 0.0175(6) Uani 1 1 d . . .
N6 N -0.1769(3) 0.7438(3) 0.4361(2) 0.0189(6) Uani 1 1 d . . .
C1 C 0.2323(4) 0.8192(3) 0.3112(3) 0.0153(7) Uani 1 1 d . . .
C2 C 0.3695(4) 0.8949(3) 0.3346(3) 0.0164(7) Uani 1 1 d . . .
H2 H 0.4645 0.8638 0.3754 0.020 Uiso 1 1 calc R . .
C3 C 0.3661(4) 1.0179(3) 0.2975(3) 0.0129(5) Uani 1 1 d . . .
C4 C 0.2216(4) 1.0560(3) 0.2387(3) 0.0165(7) Uani 1 1 d . . .
H4 H 0.2122 1.1392 0.2133 0.020 Uiso 1 1 calc R . .
C5 C 0.0921(4) 0.9722(3) 0.2176(3) 0.0161(7) Uani 1 1 d . . .
C6 C 0.2239(4) 0.6896(3) 0.3474(3) 0.0155(7) Uani 1 1 d . . .
C7 C 0.1328(4) 0.5069(3) 0.3858(3) 0.0171(7) Uani 1 1 d . . .
H7A H 0.0866 0.4244 0.3307 0.020 Uiso 1 1 calc R . .
H7B H 0.0950 0.5135 0.4553 0.020 Uiso 1 1 calc R . .
C8 C 0.3088(4) 0.5121(3) 0.4256(3) 0.0192(7) Uani 1 1 d . . .
H8A H 0.3514 0.5010 0.5102 0.023 Uiso 1 1 calc R . .
H8B H 0.3443 0.4432 0.3758 0.023 Uiso 1 1 calc R . .
C9 C -0.0644(4) 1.0009(3) 0.1513(3) 0.0161(7) Uani 1 1 d . . .
C10 C -0.2474(4) 1.1131(3) 0.0461(3) 0.0230(8) Uani 1 1 d . . .
H10A H -0.2683 1.1172 -0.0395 0.028 Uiso 1 1 calc R . .
H10B H -0.2908 1.1883 0.0825 0.028 Uiso 1 1 calc R . .
C11 C -0.3149(4) 0.9822(3) 0.0632(3) 0.0214(8) Uani 1 1 d . . .
H11A H -0.3900 0.9971 0.1069 0.026 Uiso 1 1 calc R . .
H11B H -0.3663 0.9258 -0.0146 0.026 Uiso 1 1 calc R . .
C12 C 0.5198(4) 1.1047(3) 0.3200(3) 0.0129(5) Uani 1 1 d . . .
C13 C 0.6483(4) 1.0635(3) 0.3721(3) 0.0246(8) Uani 1 1 d . . .
H13 H 0.6513 0.9826 0.4014 0.030 Uiso 1 1 calc R . .
C14 C 0.7866(4) 1.1376(3) 0.3867(3) 0.0239(8) Uani 1 1 d . . .
H14 H 0.8831 1.1076 0.4257 0.029 Uiso 1 1 calc R . .
C15 C 0.7787(4) 1.2553(4) 0.3430(3) 0.0257(8) Uani 1 1 d . . .
H15 H 0.8702 1.3068 0.3516 0.031 Uiso 1 1 calc R . .
C16 C 0.6360(4) 1.2971(3) 0.2866(3) 0.0248(8) Uani 1 1 d . . .
H16 H 0.6296 1.3780 0.2572 0.030 Uiso 1 1 calc R . .
C17 C 0.5034(4) 1.2208(3) 0.2733(3) 0.0230(8) Uani 1 1 d . . .
H17 H 0.4048 1.2468 0.2337 0.028 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
Eu1 O3 2.450(3) . ?
Eu1 O10 2.458(2) . ?
Eu1 O12 2.488(2) . ?
Eu1 O7 2.505(2) . ?
Eu1 O5 2.509(2) . ?
Eu1 O4 2.517(2) . ?
Eu1 N3 2.549(3) . ?
Eu1 N2 2.549(3) . ?
Eu1 O9 2.561(2) . ?
Eu1 N1 2.632(3) . ?
Eu1 N6 2.897(3) . ?
Eu1 N4 2.917(3) . ?
O1 C6 1.335(4) . ?
O1 C8 1.469(4) . ?
O2 C9 1.338(4) . ?
O2 C10 1.467(4) . ?
O3 H3A 0.69(5) . ?
O3 H3B 0.82(6) . ?
O4 N4 1.267(3) . ?
O5 N4 1.264(3) . ?
O6 N4 1.232(3) . ?
O7 N5 1.278(3) . ?
O8 N5 1.232(3) . ?
O9 N5 1.257(3) . ?
O10 N6 1.275(3) . ?
O11 N6 1.216(4) . ?
O12 N6 1.275(4) . ?
N1 C1 1.326(4) . ?
N1 C5 1.339(4) . ?
N2 C6 1.282(4) . ?
N2 C7 1.481(4) . ?
N3 C9 1.265(4) . ?
N3 C11 1.477(4) . ?
C1 C2 1.390(4) . ?
C1 C6 1.473(4) . ?
C2 C3 1.404(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(5) . ?
C3 C12 1.576(4) . ?
C4 C5 1.384(4) . ?
C4 H4 0.9500 . ?
C5 C9 1.473(5) . ?
C7 C8 1.534(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C11 1.537(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.271(5) . ?
C12 C17 1.389(5) . ?
C13 C14 1.411(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

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
O3 Eu1 O10 134.35(8) . . ?
O3 Eu1 O12 85.68(8) . . ?
O10 Eu1 O12 51.87(7) . . ?
O3 Eu1 O7 114.00(9) . . ?
O10 Eu1 O7 75.52(7) . . ?
O12 Eu1 O7 76.40(7) . . ?
O3 Eu1 O5 76.20(8) . . ?
O10 Eu1 O5 146.74(7) . . ?
O12 Eu1 O5 140.48(7) . . ?
O7 Eu1 O5 79.43(7) . . ?
O3 Eu1 O4 71.65(8) . . ?
O10 Eu1 O4 139.17(7) . . ?
O12 Eu1 O4 151.34(7) . . ?
O7 Eu1 O4 128.49(7) . . ?
O5 Eu1 O4 51.14(7) . . ?
O3 Eu1 N3 144.95(8) . . ?
O10 Eu1 N3 80.70(8) . . ?
O12 Eu1 N3 126.99(8) . . ?
O7 Eu1 N3 69.16(8) . . ?
O5 Eu1 N3 70.06(8) . . ?
O4 Eu1 N3 79.85(8) . . ?
O3 Eu1 N2 72.85(9) . . ?
O10 Eu1 N2 79.17(8) . . ?
O12 Eu1 N2 74.17(8) . . ?
O7 Eu1 N2 149.15(8) . . ?
O5 Eu1 N2 130.32(8) . . ?
O4 Eu1 N2 82.35(8) . . ?
N3 Eu1 N2 123.63(8) . . ?
O3 Eu1 O9 63.77(9) . . ?
O10 Eu1 O9 107.82(7) . . ?
O12 Eu1 O9 69.97(7) . . ?
O7 Eu1 O9 50.32(7) . . ?
O5 Eu1 O9 70.52(7) . . ?
O4 Eu1 O9 112.66(7) . . ?
N3 Eu1 O9 111.63(8) . . ?
N2 Eu1 O9 124.60(8) . . ?
O3 Eu1 N1 121.18(9) . . ?
O10 Eu1 N1 72.17(8) . . ?
O12 Eu1 N1 113.72(8) . . ?
O7 Eu1 N1 124.27(8) . . ?
O5 Eu1 N1 105.70(8) . . ?
O4 Eu1 N1 67.00(8) . . ?
N3 Eu1 N1 61.77(8) . . ?
N2 Eu1 N1 62.00(8) . . ?
O9 Eu1 N1 173.40(7) . . ?
O3 Eu1 N6 110.71(8) . . ?
O10 Eu1 N6 25.91(7) . . ?
O12 Eu1 N6 26.00(7) . . ?
O7 Eu1 N6 73.19(7) . . ?
O5 Eu1 N6 152.22(7) . . ?
O4 Eu1 N6 156.38(7) . . ?
N3 Eu1 N6 103.61(8) . . ?
N2 Eu1 N6 76.32(8) . . ?
O9 Eu1 N6 88.10(8) . . ?
N1 Eu1 N6 93.70(8) . . ?
O3 Eu1 N4 70.90(8) . . ?
O10 Eu1 N4 153.23(7) . . ?
O12 Eu1 N4 154.85(7) . . ?
O7 Eu1 N4 104.37(8) . . ?
O5 Eu1 N4 25.55(7) . . ?
O4 Eu1 N4 25.64(7) . . ?
N3 Eu1 N4 74.56(8) . . ?
N2 Eu1 N4 106.18(8) . . ?
O9 Eu1 N4 90.92(7) . . ?
N1 Eu1 N4 87.02(8) . . ?
N6 Eu1 N4 177.43(7) . . ?
C6 O1 C8 105.6(2) . . ?
C9 O2 C10 105.5(2) . . ?
Eu1 O3 H3A 121(4) . . ?
Eu1 O3 H3B 111(4) . . ?
H3A O3 H3B 110(5) . . ?
N4 O4 Eu1 95.09(17) . . ?
N4 O5 Eu1 95.55(17) . . ?
N5 O7 Eu1 97.58(17) . . ?
N5 O9 Eu1 95.44(17) . . ?
N6 O10 Eu1 96.69(17) . . ?
N6 O12 Eu1 95.21(17) . . ?
C1 N1 C5 116.9(3) . . ?
C1 N1 Eu1 121.6(2) . . ?
C5 N1 Eu1 121.4(2) . . ?
C6 N2 C7 105.8(3) . . ?
C6 N2 Eu1 121.2(2) . . ?
C7 N2 Eu1 132.96(19) . . ?
C9 N3 C11 106.5(3) . . ?
C9 N3 Eu1 122.1(2) . . ?
C11 N3 Eu1 131.1(2) . . ?
O6 N4 O5 121.3(3) . . ?
O6 N4 O4 120.7(3) . . ?
O5 N4 O4 118.0(3) . . ?
O6 N4 Eu1 176.2(2) . . ?
O5 N4 Eu1 58.90(14) . . ?
O4 N4 Eu1 59.26(14) . . ?
O8 N5 O9 122.8(3) . . ?
O8 N5 O7 120.8(3) . . ?
O9 N5 O7 116.4(3) . . ?
O8 N5 Eu1 175.4(2) . . ?
O9 N5 Eu1 59.53(15) . . ?
O7 N5 Eu1 57.07(14) . . ?
O11 N6 O10 121.9(3) . . ?
O11 N6 O12 122.1(3) . . ?
O10 N6 O12 116.0(3) . . ?
O11 N6 Eu1 175.9(2) . . ?
O10 N6 Eu1 57.40(14) . . ?
O12 N6 Eu1 58.79(14) . . ?
N1 C1 C2 123.8(3) . . ?
N1 C1 C6 112.8(3) . . ?
C2 C1 C6 123.3(3) . . ?
C1 C2 C3 119.3(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 116.5(3) . . ?
C4 C3 C12 122.8(3) . . ?
C2 C3 C12 120.6(3) . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 123.8(3) . . ?
N1 C5 C9 112.6(3) . . ?
C4 C5 C9 123.6(3) . . ?
N2 C6 O1 119.4(3) . . ?
N2 C6 C1 121.9(3) . . ?
O1 C6 C1 118.6(3) . . ?
N2 C7 C8 104.2(2) . . ?
N2 C7 H7A 110.9 . . ?
C8 C7 H7A 110.9 . . ?
N2 C7 H7B 110.9 . . ?
C8 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
O1 C8 C7 103.4(2) . . ?
O1 C8 H8A 111.1 . . ?
C7 C8 H8A 111.1 . . ?
O1 C8 H8B 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
N3 C9 O2 119.9(3) . . ?
N3 C9 C5 121.9(3) . . ?
O2 C9 C5 118.2(3) . . ?
O2 C10 C11 103.9(2) . . ?
O2 C10 H10A 111.0 . . ?
C11 C10 H10A 111.0 . . ?
O2 C10 H10B 111.0 . . ?
C11 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
N3 C11 C10 104.3(3) . . ?
N3 C11 H11A 110.9 . . ?
C10 C11 H11A 110.9 . . ?
N3 C11 H11B 110.9 . . ?
C10 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C13 C12 C17 124.2(3) . . ?
C13 C12 C3 120.0(3) . . ?
C17 C12 C3 115.7(3) . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 118.7(3) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C16 119.5(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C12 117.5(3) . . ?
C16 C17 H17 121.3 . . ?
C12 C17 H17 121.3 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.200
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.098
####################################################################### 
# 
# 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_abd196_0m
_database_code_depnum_ccdc_archive 'CCDC 890800'
_audit_update_record             
;
2012-07-06 deposited with the CCDC.	2020-11-24 downloaded from the CCDC.
;
#TrackingRef 'PyboxPh.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 N3 O2'
_chemical_formula_weight         293.32

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   P21/c

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

_cell_length_a                   16.3794(4)
_cell_length_b                   7.2856(2)
_cell_length_c                   11.7073(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.229(1)
_cell_angle_gamma                90.00
_cell_volume                     1385.97(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8897
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      33.17

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_T_max  0.9972
_exptl_absorpt_process_details   'Bruker SADABS (Bruker 2005)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD'
_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            27021
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         33.22
_reflns_number_total             5286
_reflns_number_gt                4053
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker, 2001)'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 2001)'

_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)+(0.0855P)²+0.4038P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5286
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1547
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.38268(8) 0.5792(2) 0.52136(11) 0.0286(3) Uani 1 1 d . . .
C2 C 0.29521(8) 0.56839(17) 0.45743(10) 0.0243(2) Uani 1 1 d . . .
C3 C 0.29266(7) 0.50664(16) 0.64164(9) 0.0207(2) Uani 1 1 d . . .
C4 C 0.26199(7) 0.46226(15) 0.75217(9) 0.0176(2) Uani 1 1 d . . .
C5 C 0.17803(7) 0.43300(15) 0.75328(9) 0.01741(19) Uani 1 1 d . . .
C6 C 0.14761(6) 0.39845(14) 0.85772(9) 0.01600(19) Uani 1 1 d . . .
C7 C 0.20514(6) 0.39294(14) 0.95635(9) 0.01678(19) Uani 1 1 d . . .
C8 C 0.28801(6) 0.42137(14) 0.94608(9) 0.01721(19) Uani 1 1 d . . .
C9 C 0.34815(7) 0.41819(16) 1.05106(10) 0.0198(2) Uani 1 1 d . . .
C10 C 0.40882(8) 0.4289(2) 1.22931(11) 0.0300(3) Uani 1 1 d . . .
C11 C 0.47397(8) 0.3937(3) 1.14996(11) 0.0394(4) Uani 1 1 d . . .
C12 C 0.05844(6) 0.37263(14) 0.86357(9) 0.01634(19) Uani 1 1 d . . .
C13 C 0.00048(7) 0.45189(15) 0.77994(10) 0.0193(2) Uani 1 1 d . . .
C14 C -0.08338(7) 0.43034(16) 0.78526(11) 0.0221(2) Uani 1 1 d . . .
C15 C -0.11059(7) 0.32999(16) 0.87398(10) 0.0223(2) Uani 1 1 d . . .
C16 C -0.05347(7) 0.25140(16) 0.95799(10) 0.0219(2) Uani 1 1 d . . .
C17 C 0.03050(7) 0.27243(15) 0.95283(9) 0.0195(2) Uani 1 1 d . . .
H1 H 0.1899(10) 0.368(2) 1.0313(14) 0.026(4) Uiso 1 1 d . . .
H2 H 0.0718(9) 0.213(2) 1.0109(13) 0.022(4) Uiso 1 1 d . . .
H3 H 0.0189(9) 0.527(2) 0.7176(13) 0.022(4) Uiso 1 1 d . . .
H4 H -0.0717(9) 0.182(2) 1.0191(13) 0.026(4) Uiso 1 1 d . . .
H5 H -0.1684(10) 0.315(2) 0.8765(13) 0.027(4) Uiso 1 1 d . . .
H6 H 0.1436(11) 0.432(2) 0.6781(15) 0.034(4) Uiso 1 1 d . . .
H7 H 0.2879(11) 0.478(2) 0.3944(15) 0.033(4) Uiso 1 1 d . . .
H8 H 0.4174(10) 0.483(2) 0.5001(14) 0.028(4) Uiso 1 1 d . . .
H9 H 0.4098(10) 0.699(3) 0.5208(15) 0.035(4) Uiso 1 1 d . . .
H10 H 0.2757(10) 0.688(2) 0.4216(15) 0.033(4) Uiso 1 1 d . . .
H11 H 0.4175(13) 0.552(3) 1.2738(18) 0.051(6) Uiso 1 1 d . . .
H12 H 0.4095(12) 0.329(3) 1.2903(17) 0.047(5) Uiso 1 1 d . . .
H13 H 0.5194(15) 0.487(3) 1.152(2) 0.062(6) Uiso 1 1 d . . .
H14 H -0.1219(10) 0.485(2) 0.7280(15) 0.029(4) Uiso 1 1 d . . .
H15 H 0.5126(17) 0.291(4) 1.165(2) 0.088(8) Uiso 1 1 d . . .
N1 N 0.24411(6) 0.51546(14) 0.54651(8) 0.01884(18) Uani 1 1 d . . .
N2 N 0.31760(6) 0.45620(13) 0.84652(8) 0.01865(19) Uani 1 1 d . . .
N3 N 0.32984(6) 0.43660(16) 1.15285(9) 0.0256(2) Uani 1 1 d . . .
O1 O 0.37289(6) 0.54021(16) 0.64151(8) 0.0314(2) Uani 1 1 d . . .
O2 O 0.42817(5) 0.39591(16) 1.03494(7) 0.0298(2) 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
C1 O1 1.4635(15) . ?
C1 C2 1.5328(19) . ?
C1 H8 0.957(17) . ?
C1 H9 0.979(19) . ?
C2 N1 1.4685(15) . ?
C2 H7 0.988(18) . ?
C2 H10 1.002(18) . ?
C3 N1 1.2861(14) . ?
C3 O1 1.3369(14) . ?
C3 C4 1.4815(15) . ?
C4 N2 1.3411(14) . ?
C4 C5 1.3932(15) . ?
C5 C6 1.4000(14) . ?
C5 H6 0.984(18) . ?
C6 C7 1.3960(14) . ?
C6 C12 1.4828(14) . ?
C7 C8 1.3931(15) . ?
C7 H1 0.959(16) . ?
C8 N2 1.3418(14) . ?
C8 C9 1.4753(15) . ?
C9 N3 1.2720(15) . ?
C9 O2 1.3572(14) . ?
C10 N3 1.4787(16) . ?
C10 C11 1.522(2) . ?
C10 H11 1.04(2) . ?
C10 H12 1.02(2) . ?
C11 O2 1.4568(15) . ?
C11 H13 1.00(2) . ?
C11 H15 0.98(3) . ?
C12 C17 1.3981(15) . ?
C12 C13 1.3997(15) . ?
C13 C14 1.3917(15) . ?
C13 H3 0.989(16) . ?
C14 C15 1.3887(17) . ?
C14 H14 0.948(17) . ?
C15 C16 1.3925(17) . ?
C15 H5 0.958(15) . ?
C16 C17 1.3927(15) . ?
C16 H4 0.954(16) . ?
C17 H2 0.997(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 104.52(10) . . ?
O1 C1 H8 104.4(10) . . ?
C2 C1 H8 112.7(10) . . ?
O1 C1 H9 106.5(10) . . ?
C2 C1 H9 116.1(10) . . ?
H8 C1 H9 111.5(14) . . ?
N1 C2 C1 104.35(9) . . ?
N1 C2 H7 109.2(10) . . ?
C1 C2 H7 114.7(10) . . ?
N1 C2 H10 110.2(10) . . ?
C1 C2 H10 112.9(10) . . ?
H7 C2 H10 105.5(14) . . ?
N1 C3 O1 119.38(10) . . ?
N1 C3 C4 121.77(10) . . ?
O1 C3 C4 118.84(10) . . ?
N2 C4 C5 123.79(10) . . ?
N2 C4 C3 117.17(10) . . ?
C5 C4 C3 119.03(10) . . ?
C4 C5 C6 119.73(10) . . ?
C4 C5 H6 116.6(10) . . ?
C6 C5 H6 123.6(10) . . ?
C7 C6 C5 116.76(9) . . ?
C7 C6 C12 121.63(9) . . ?
C5 C6 C12 121.60(9) . . ?
C8 C7 C6 119.20(10) . . ?
C8 C7 H1 118.3(10) . . ?
C6 C7 H1 122.5(10) . . ?
N2 C8 C7 124.43(10) . . ?
N2 C8 C9 116.76(9) . . ?
C7 C8 C9 118.78(9) . . ?
N3 C9 O2 119.24(10) . . ?
N3 C9 C8 124.57(10) . . ?
O2 C9 C8 116.19(9) . . ?
N3 C10 C11 105.31(10) . . ?
N3 C10 H11 109.0(11) . . ?
C11 C10 H11 112.9(12) . . ?
N3 C10 H12 112.5(11) . . ?
C11 C10 H12 111.2(11) . . ?
H11 C10 H12 106.0(16) . . ?
O2 C11 C10 104.08(10) . . ?
O2 C11 H13 107.8(14) . . ?
C10 C11 H13 116.7(14) . . ?
O2 C11 H15 114.6(17) . . ?
C10 C11 H15 120.7(15) . . ?
H13 C11 H15 93(2) . . ?
C17 C12 C13 118.76(10) . . ?
C17 C12 C6 121.18(9) . . ?
C13 C12 C6 120.05(9) . . ?
C14 C13 C12 120.56(10) . . ?
C14 C13 H3 119.3(9) . . ?
C12 C13 H3 120.1(9) . . ?
C15 C14 C13 120.29(11) . . ?
C15 C14 H14 120.1(10) . . ?
C13 C14 H14 119.6(10) . . ?
C14 C15 C16 119.64(10) . . ?
C14 C15 H5 119.7(9) . . ?
C16 C15 H5 120.7(9) . . ?
C15 C16 C17 120.23(10) . . ?
C15 C16 H4 120.1(9) . . ?
C17 C16 H4 119.7(9) . . ?
C16 C17 C12 120.52(10) . . ?
C16 C17 H2 120.8(9) . . ?
C12 C17 H2 118.6(9) . . ?
C3 N1 C2 106.41(9) . . ?
C4 N2 C8 116.08(9) . . ?
C9 N3 C10 105.77(10) . . ?
C3 O1 C1 105.26(9) . . ?
C9 O2 C11 105.48(9) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        33.22
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.081
####################################################################### 
# 
# 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_abd202_1_0m
_database_code_depnum_ccdc_archive 'CCDC 890801'
_audit_update_record             
;
2012-07-06 deposited with the CCDC.	2020-11-24 downloaded from the CCDC.
;
#TrackingRef 'TbPyboxPh.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H19 N6 O14 Tb'
_chemical_formula_weight         690.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.8052(1)
_cell_length_b                   11.8910(1)
_cell_length_c                   14.2668(2)
_cell_angle_alpha                72.557(1)
_cell_angle_beta                 86.355(1)
_cell_angle_gamma                77.223(1)
_cell_volume                     1231.95(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9889
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      29.30

_exptl_crystal_description       neddle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    2.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3502
_exptl_absorpt_correction_T_max  0.7372
_exptl_absorpt_process_details   'Bruker SADABS (Bruker 2005)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex CCD'
_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            33251
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         29.62
_reflns_number_total             6904
_reflns_number_gt                6058
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Smart (Bruker, 2001)'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 2001)'

_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)+(0.0506P)²+3.3552P] 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_number_reflns         6904
_refine_ls_number_parameters     349
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0990
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.113
_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
Tb1 Tb -0.01630(2) 0.766435(17) 0.349218(14) 0.01486(7) Uani 1 1 d . . .
O6 O 0.4281(4) 0.9768(3) 0.2921(2) 0.0209(6) Uani 1 1 d . . .
O13 O -0.1859(7) 0.7974(4) 0.5044(3) 0.0574(14) Uani 1 1 d . . .
O14 O 0.0829(5) 0.7073(4) 0.5230(3) 0.0361(9) Uani 1 1 d . . .
O16 O -0.1786(4) 0.9780(3) 0.3360(3) 0.0284(7) Uani 1 1 d . . .
O17 O -0.1435(4) 0.9257(3) 0.2028(2) 0.0251(7) Uani 1 1 d . . .
O18 O -0.3262(4) 0.7452(3) 0.3428(2) 0.0226(6) Uani 1 1 d . . .
O19 O -0.1485(4) 0.5911(3) 0.4364(2) 0.0214(6) Uani 1 1 d . . .
O20 O 0.0882(4) 0.5925(3) 0.0945(2) 0.0253(7) Uani 1 1 d . . .
O21 O -0.4193(5) 0.5823(3) 0.4218(3) 0.0379(9) Uani 1 1 d . . .
O24 O -0.2747(5) 1.1103(3) 0.1965(3) 0.0414(10) Uani 1 1 d . . .
O30 O 0.2214(4) 0.5907(3) 0.3897(2) 0.0213(6) Uani 1 1 d . . .
N2 N 0.2162(4) 0.7863(3) 0.2129(3) 0.0170(7) Uani 1 1 d . . .
N9 N 0.2032(5) 0.8872(3) 0.3568(3) 0.0192(7) Uani 1 1 d . . .
N14 N -0.2012(5) 1.0083(3) 0.2443(3) 0.0269(9) Uani 1 1 d . . .
N15 N -0.3025(5) 0.6392(3) 0.4007(3) 0.0216(7) Uani 1 1 d . . .
N16 N -0.0306(5) 0.6582(3) 0.2222(3) 0.0195(7) Uani 1 1 d . . .
C1 C 0.3367(5) 0.8509(4) 0.2094(3) 0.0159(7) Uani 1 1 d . . .
C2 C 0.4674(5) 0.8619(4) 0.1389(3) 0.0183(8) Uani 1 1 d . . .
H2 H 0.5498 0.9098 0.1395 0.022 Uiso 1 1 calc R . .
C4 C 0.3496(5) 0.7354(4) 0.0705(3) 0.0202(8) Uani 1 1 d . . .
H4 H 0.3491 0.6938 0.0231 0.024 Uiso 1 1 calc R . .
C5 C 0.2231(5) 0.7300(4) 0.1437(3) 0.0192(8) Uani 1 1 d . . .
C6 C 0.6241(5) 0.8071(4) -0.0113(3) 0.0211(9) Uani 1 1 d . . .
C7 C 0.7606(6) 0.8605(4) -0.0016(3) 0.0245(9) Uani 1 1 d . . .
H7 H 0.7614 0.8956 0.0500 0.029 Uiso 1 1 calc R . .
C8 C 0.8955(6) 0.8610(4) -0.0696(4) 0.0274(10) Uani 1 1 d . . .
H8 H 0.9900 0.8976 -0.0651 0.033 Uiso 1 1 calc R . .
C9 C 0.8935(6) 0.8083(5) -0.1442(4) 0.0294(10) Uani 1 1 d . . .
H9 H 0.9862 0.8090 -0.1907 0.035 Uiso 1 1 calc R . .
C10 C 0.7550(7) 0.7548(5) -0.1503(4) 0.0332(11) Uani 1 1 d . . .
H10 H 0.7524 0.7181 -0.2007 0.040 Uiso 1 1 calc R . .
C11 C 0.0861(5) 0.6584(4) 0.1557(3) 0.0185(8) Uani 1 1 d . . .
C12 C -0.0655(6) 0.5380(4) 0.1210(4) 0.0271(10) Uani 1 1 d . . .
H12A H -0.0314 0.4492 0.1360 0.033 Uiso 1 1 calc R . .
H12B H -0.1530 0.5698 0.0670 0.033 Uiso 1 1 calc R . .
C13 C -0.1392(6) 0.5744(4) 0.2125(3) 0.0225(9) Uani 1 1 d . . .
H13A H -0.2647 0.6152 0.2034 0.027 Uiso 1 1 calc R . .
H13B H -0.1269 0.5031 0.2713 0.027 Uiso 1 1 calc R . .
C14 C 0.2220(6) 0.9606(5) 0.4215(4) 0.0268(10) Uani 1 1 d . . .
H14A H 0.2323 0.9111 0.4913 0.032 Uiso 1 1 calc R . .
H14B H 0.1206 1.0294 0.4142 0.032 Uiso 1 1 calc R . .
C22 C 0.3928(6) 1.0047(5) 0.3855(4) 0.0292(10) Uani 1 1 d . . .
H22A H 0.3761 1.0924 0.3759 0.035 Uiso 1 1 calc R . .
H22B H 0.4900 0.9614 0.4328 0.035 Uiso 1 1 calc R . .
C23 C 0.3189(5) 0.9055(4) 0.2897(3) 0.0176(8) Uani 1 1 d . . .
C24 C 0.6194(6) 0.7555(5) -0.0813(4) 0.0306(11) Uani 1 1 d . . .
H24 H 0.5241 0.7191 -0.0847 0.037 Uiso 1 1 calc R . .
C25 C 0.4784(6) 0.8027(4) 0.0666(3) 0.0202(8) Uani 1 1 d . . .
N1 N -0.0587(7) 0.7410(4) 0.5624(3) 0.0355(10) Uani 1 1 d . . .
O1 O -0.0718(7) 0.7212(4) 0.6513(3) 0.0587(14) Uani 1 1 d . . .
O51A O 0.5479(6) 0.4388(4) 0.1875(4) 0.0289(9) Uani 0.80 1 d PU A 1
O51B O 0.561(2) 0.3925(16) 0.2393(15) 0.0289(9) Uani 0.20 1 d PU B 2
O52A O 0.4607(9) 0.2949(6) 0.3908(6) 0.0307(11) Uani 0.50 1 d P C 1
O52B O 0.5771(9) 0.3166(6) 0.3342(6) 0.0307(11) Uani 0.50 1 d P B 2


_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
Tb1 O30 2.416(3) . ?
Tb1 O17 2.449(3) . ?
Tb1 O19 2.488(3) . ?
Tb1 O14 2.489(4) . ?
Tb1 N9 2.493(3) . ?
Tb1 O18 2.497(3) . ?
Tb1 O16 2.512(3) . ?
Tb1 N16 2.538(4) . ?
Tb1 N2 2.568(3) . ?
Tb1 O13 2.587(4) . ?
Tb1 N15 2.905(3) . ?
Tb1 N14 2.907(4) . ?
O6 C23 1.337(5) . ?
O6 C22 1.464(6) . ?
O13 N1 1.263(6) . ?
O14 N1 1.249(6) . ?
O16 N14 1.261(6) . ?
O17 N14 1.279(5) . ?
O18 N15 1.264(5) . ?
O19 N15 1.277(5) . ?
O20 C11 1.332(5) . ?
O20 C12 1.463(6) . ?
O21 N15 1.223(5) . ?
O24 N14 1.229(5) . ?
N2 C1 1.330(5) . ?
N2 C5 1.341(6) . ?
N9 C23 1.276(5) . ?
N9 C14 1.481(6) . ?
N16 C11 1.273(6) . ?
N16 C13 1.483(5) . ?
C1 C2 1.386(6) . ?
C1 C23 1.463(6) . ?
C2 C25 1.401(6) . ?
C2 H2 0.9500 . ?
C4 C5 1.388(6) . ?
C4 C25 1.406(6) . ?
C4 H4 0.9500 . ?
C5 C11 1.481(6) . ?
C6 C24 1.326(7) . ?
C6 C7 1.389(6) . ?
C6 C25 1.537(6) . ?
C7 C8 1.385(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(7) . ?
C9 H9 0.9500 . ?
C10 C24 1.399(7) . ?
C10 H10 0.9500 . ?
C12 C13 1.536(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C22 1.541(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C24 H24 0.9500 . ?
N1 O1 1.221(6) . ?
O51B O52B 1.38(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O30 Tb1 O17 138.26(11) . . ?
O30 Tb1 O19 73.08(10) . . ?
O17 Tb1 O19 124.23(10) . . ?
O30 Tb1 O14 67.14(12) . . ?
O17 Tb1 O14 148.76(13) . . ?
O19 Tb1 O14 74.63(11) . . ?
O30 Tb1 N9 87.21(11) . . ?
O17 Tb1 N9 88.82(12) . . ?
O19 Tb1 N9 146.11(11) . . ?
O14 Tb1 N9 72.35(12) . . ?
O30 Tb1 O18 120.74(10) . . ?
O17 Tb1 O18 74.94(10) . . ?
O19 Tb1 O18 51.60(9) . . ?
O14 Tb1 O18 110.16(11) . . ?
N9 Tb1 O18 151.19(11) . . ?
O30 Tb1 O16 157.67(11) . . ?
O17 Tb1 O16 51.47(12) . . ?
O19 Tb1 O16 120.75(11) . . ?
O14 Tb1 O16 98.18(13) . . ?
N9 Tb1 O16 71.89(11) . . ?
O18 Tb1 O16 79.41(10) . . ?
O30 Tb1 N16 74.35(11) . . ?
O17 Tb1 N16 75.08(12) . . ?
O19 Tb1 N16 74.84(11) . . ?
O14 Tb1 N16 136.16(13) . . ?
N9 Tb1 N16 126.67(11) . . ?
O18 Tb1 N16 72.49(11) . . ?
O16 Tb1 N16 124.44(11) . . ?
O30 Tb1 N2 70.17(11) . . ?
O17 Tb1 N2 71.01(11) . . ?
O19 Tb1 N2 129.90(11) . . ?
O14 Tb1 N2 118.48(12) . . ?
N9 Tb1 N2 63.32(11) . . ?
O18 Tb1 N2 129.39(11) . . ?
O16 Tb1 N2 105.65(11) . . ?
N16 Tb1 N2 63.35(11) . . ?
O30 Tb1 O13 111.54(12) . . ?
O17 Tb1 O13 110.20(12) . . ?
O19 Tb1 O13 68.26(15) . . ?
O14 Tb1 O13 49.51(14) . . ?
N9 Tb1 O13 95.21(16) . . ?
O18 Tb1 O13 69.38(15) . . ?
O16 Tb1 O13 64.15(13) . . ?
N16 Tb1 O13 138.12(16) . . ?
N2 Tb1 O13 158.53(16) . . ?
O30 Tb1 N15 97.08(10) . . ?
O17 Tb1 N15 99.48(11) . . ?
O19 Tb1 N15 25.94(10) . . ?
O14 Tb1 N15 92.78(11) . . ?
N9 Tb1 N15 161.60(12) . . ?
O18 Tb1 N15 25.66(10) . . ?
O16 Tb1 N15 100.48(11) . . ?
N16 Tb1 N15 71.59(11) . . ?
N2 Tb1 N15 134.92(11) . . ?
O13 Tb1 N15 66.55(16) . . ?
O30 Tb1 N14 157.66(11) . . ?
O17 Tb1 N14 25.87(12) . . ?
O19 Tb1 N14 127.13(10) . . ?
O14 Tb1 N14 123.39(13) . . ?
N9 Tb1 N14 78.83(11) . . ?
O18 Tb1 N14 76.32(10) . . ?
O16 Tb1 N14 25.61(12) . . ?
N16 Tb1 N14 100.12(12) . . ?
N2 Tb1 N14 87.91(11) . . ?
O13 Tb1 N14 87.24(13) . . ?
N15 Tb1 N14 101.66(10) . . ?
C23 O6 C22 105.3(3) . . ?
N1 O13 Tb1 94.6(3) . . ?
N1 O14 Tb1 99.8(3) . . ?
N14 O16 Tb1 95.0(3) . . ?
N14 O17 Tb1 97.5(3) . . ?
N15 O18 Tb1 95.5(2) . . ?
N15 O19 Tb1 95.6(2) . . ?
C11 O20 C12 105.2(3) . . ?
C1 N2 C5 117.4(4) . . ?
C1 N2 Tb1 121.2(3) . . ?
C5 N2 Tb1 121.4(3) . . ?
C23 N9 C14 106.2(3) . . ?
C23 N9 Tb1 120.7(3) . . ?
C14 N9 Tb1 132.8(3) . . ?
O24 N14 O16 123.0(5) . . ?
O24 N14 O17 121.1(5) . . ?
O16 N14 O17 116.0(4) . . ?
O24 N14 Tb1 177.2(4) . . ?
O16 N14 Tb1 59.4(2) . . ?
O17 N14 Tb1 56.6(2) . . ?
O21 N15 O18 122.7(4) . . ?
O21 N15 O19 120.0(4) . . ?
O18 N15 O19 117.3(3) . . ?
O21 N15 Tb1 177.8(3) . . ?
O18 N15 Tb1 58.80(19) . . ?
O19 N15 Tb1 58.49(19) . . ?
C11 N16 C13 105.9(4) . . ?
C11 N16 Tb1 120.2(3) . . ?
C13 N16 Tb1 133.4(3) . . ?
N2 C1 C2 123.4(4) . . ?
N2 C1 C23 112.5(3) . . ?
C2 C1 C23 124.1(4) . . ?
C1 C2 C25 120.2(4) . . ?
C1 C2 H2 119.9 . . ?
C25 C2 H2 119.9 . . ?
C5 C4 C25 119.7(4) . . ?
C5 C4 H4 120.1 . . ?
C25 C4 H4 120.1 . . ?
N2 C5 C4 123.3(4) . . ?
N2 C5 C11 113.0(4) . . ?
C4 C5 C11 123.6(4) . . ?
C24 C6 C7 122.9(5) . . ?
C24 C6 C25 119.4(4) . . ?
C7 C6 C25 117.6(4) . . ?
C8 C7 C6 117.9(5) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C7 C8 C9 120.5(5) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C24 119.3(5) . . ?
C9 C10 H10 120.4 . . ?
C24 C10 H10 120.4 . . ?
N16 C11 O20 120.2(4) . . ?
N16 C11 C5 121.8(4) . . ?
O20 C11 C5 118.0(4) . . ?
O20 C12 C13 104.2(3) . . ?
O20 C12 H12A 110.9 . . ?
C13 C12 H12A 110.9 . . ?
O20 C12 H12B 110.9 . . ?
C13 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
N16 C13 C12 104.0(4) . . ?
N16 C13 H13A 111.0 . . ?
C12 C13 H13A 111.0 . . ?
N16 C13 H13B 111.0 . . ?
C12 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
N9 C14 C22 103.6(3) . . ?
N9 C14 H14A 111.0 . . ?
C22 C14 H14A 111.0 . . ?
N9 C14 H14B 111.0 . . ?
C22 C14 H14B 111.0 . . ?
H14A C14 H14B 109.0 . . ?
O6 C22 C14 103.6(3) . . ?
O6 C22 H22A 111.0 . . ?
C14 C22 H22A 111.0 . . ?
O6 C22 H22B 111.0 . . ?
C14 C22 H22B 111.0 . . ?
H22A C22 H22B 109.0 . . ?
N9 C23 O6 119.6(4) . . ?
N9 C23 C1 122.2(4) . . ?
O6 C23 C1 118.2(4) . . ?
C6 C24 C10 119.9(5) . . ?
C6 C24 H24 120.1 . . ?
C10 C24 H24 120.1 . . ?
C2 C25 C4 116.1(4) . . ?
C2 C25 C6 122.8(4) . . ?
C4 C25 C6 121.1(4) . . ?
O1 N1 O14 121.7(5) . . ?
O1 N1 O13 122.6(5) . . ?
O14 N1 O13 115.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        29.62
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         2.824
_refine_diff_density_min         -2.288
_refine_diff_density_rms         0.172



####################################################################### 
# 
# 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_abd207
_database_code_depnum_ccdc_archive 'CCDC 890799'
_audit_update_record             
;
2012-07-06 deposited with the CCDC.	2020-11-24 downloaded from the CCDC.
;
#TrackingRef 'Pybox2Th.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 N3 O2 S'
_chemical_formula_weight         299.34

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   5.9472(2)
_cell_length_b                   16.0747(6)
_cell_length_c                   14.3716(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.503(1)
_cell_angle_gamma                90.00
_cell_volume                     1371.35(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7483
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      31.18

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9275
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_process_details   'SADABS SHELXL-97 (Sheldrick, 2001)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD'
_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            30136
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4006
_reflns_number_gt                3216
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker, 2001)'
_computing_cell_refinement       'Bruker SMART (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2001)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 2001)'

_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)+(0.0749P)²+1.0664P] 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_number_reflns         4006
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1490
_refine_ls_wR_factor_gt          0.1374
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
C1A C -0.0498(3) 0.89558(10) 0.04772(11) 0.0214(2) Uani 0.5400(15) 1 d P A 1
C2A C -0.2613(8) 0.9050(3) -0.0003(4) 0.0214(2) Uani 0.5400(15) 1 d P A 1
H2A H -0.3731 0.9413 0.0211 0.026 Uiso 0.5400(15) 1 calc PR A 1
C3A C -0.2966(7) 0.8587(3) -0.0795(3) 0.0214(2) Uani 0.5400(15) 1 d P A 1
H3A H -0.4324 0.8569 -0.1179 0.026 Uiso 0.5400(15) 1 calc PR A 1
C4A C -0.1015(6) 0.8147(3) -0.0948(3) 0.0214(2) Uani 0.5400(15) 1 d P A 1
H4A H -0.0867 0.7795 -0.1471 0.026 Uiso 0.5400(15) 1 calc PR A 1
S1A S 0.11170(17) 0.83015(8) -0.00960(10) 0.0227(2) Uani 0.5400(15) 1 d P A 1
C1B C -0.0498(3) 0.89558(10) 0.04772(11) 0.0214(2) Uani 0.4600(15) 1 d P A 2
C2B C 0.0722(11) 0.8411(4) -0.0089(5) 0.0214(2) Uani 0.4600(15) 1 d P A 2
H2B H 0.2247 0.8257 0.0050 0.026 Uiso 0.4600(15) 1 calc PR A 2
C3B C -0.0583(7) 0.8124(4) -0.0883(4) 0.0214(2) Uani 0.4600(15) 1 d P A 2
H3B H -0.0084 0.7740 -0.1329 0.026 Uiso 0.4600(15) 1 calc PR A 2
C4B C -0.2658(7) 0.8481(3) -0.0910(3) 0.0214(2) Uani 0.5400(15) 1 d P A 2
H4B H -0.3770 0.8382 -0.1401 0.026 Uiso 0.5400(15) 1 calc PR A 2
S1B S -0.31109(17) 0.91274(9) 0.00157(10) 0.0227(2) Uani 0.4600(15) 1 d P A 2
C1 C -0.0101(3) 1.03775(10) 0.25694(11) 0.0203(3) Uani 1 1 d . . .
C2 C -0.0915(3) 1.00051(10) 0.17425(11) 0.0200(3) Uani 1 1 d . A .
H2P H -0.2296 1.0185 0.1441 0.024 Uiso 1 1 calc R . .
C3 C 0.0313(3) 0.93664(10) 0.13597(11) 0.0188(3) Uani 1 1 d . . .
C4 C 0.2324(3) 0.91271(10) 0.18484(11) 0.0209(3) Uani 1 1 d . A .
H4P H 0.3224 0.8694 0.1618 0.025 Uiso 1 1 calc R . .
C5 C 0.2978(3) 0.95344(10) 0.26761(11) 0.0204(3) Uani 1 1 d . . .
C6 C -0.1436(3) 1.10432(11) 0.29793(11) 0.0238(3) Uani 1 1 d . . .
C7 C -0.2469(4) 1.18761(17) 0.41232(17) 0.0524(7) Uani 1 1 d . . .
H7A H -0.1821 1.2425 0.4301 0.063 Uiso 1 1 calc R . .
H7B H -0.3249 1.1648 0.4656 0.063 Uiso 1 1 calc R . .
C8 C -0.4086(3) 1.19483(13) 0.32563(14) 0.0342(4) Uani 1 1 d . . .
H8B H -0.5642 1.1805 0.3405 0.041 Uiso 1 1 calc R . .
H8A H -0.4077 1.2520 0.3001 0.041 Uiso 1 1 calc R . .
C9 C 0.5032(3) 0.92540(11) 0.32285(11) 0.0232(3) Uani 1 1 d . A .
C10 C 0.7590(4) 0.92952(15) 0.44340(14) 0.0387(5) Uani 1 1 d . A .
H10B H 0.7241 0.9078 0.5054 0.046 Uiso 1 1 calc R . .
H10A H 0.8897 0.9676 0.4510 0.046 Uiso 1 1 calc R . .
C11 C 0.8055(3) 0.85874(13) 0.37666(15) 0.0332(4) Uani 1 1 d . A .
H11A H 0.9523 0.8668 0.3490 0.040 Uiso 1 1 calc R . .
H11B H 0.8073 0.8046 0.4095 0.040 Uiso 1 1 calc R . .
N1 N 0.1821(2) 1.01538(9) 0.30417(9) 0.0216(3) Uani 1 1 d . A .
N2 N -0.3224(3) 1.13478(10) 0.25873(10) 0.0276(3) Uani 1 1 d . . .
N3 N 0.6184(3) 0.86193(10) 0.30367(12) 0.0291(3) Uani 1 1 d . . .
O1 O -0.0726(3) 1.13086(10) 0.38422(10) 0.0381(4) Uani 1 1 d . . .
O2 O 0.5642(2) 0.97173(10) 0.39841(9) 0.0363(3) 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
C1A C2A 1.405(5) . ?
C1A C3 1.484(2) . ?
C1A S1A 1.6745(19) . ?
C2A C3A 1.366(7) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.387(5) . ?
C3A H3A 0.9500 . ?
C4A S1A 1.726(4) . ?
C4A H4A 0.9500 . ?
C2B C3B 1.418(9) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.359(5) . ?
C3B H3B 0.9500 . ?
C4B S1B 1.723(4) . ?
C4B H4B 0.9500 . ?
C1 N1 1.342(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.476(2) . ?
C2 C3 1.393(2) . ?
C2 H2P 0.9500 . ?
C3 C4 1.403(2) . ?
C4 C5 1.392(2) . ?
C4 H4P 0.9500 . ?
C5 N1 1.336(2) . ?
C5 C9 1.486(2) . ?
C6 N2 1.271(2) . ?
C6 O1 1.354(2) . ?
C7 O1 1.456(3) . ?
C7 C8 1.531(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N2 1.476(2) . ?
C8 H8B 0.9900 . ?
C8 H8A 0.9900 . ?
C9 N3 1.269(2) . ?
C9 O2 1.348(2) . ?
C10 O2 1.459(2) . ?
C10 C11 1.524(3) . ?
C10 H10B 0.9900 . ?
C10 H10A 0.9900 . ?
C11 N3 1.483(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

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
C2A C1A C3 127.3(2) . . ?
C2A C1A S1A 110.4(2) . . ?
C3 C1A S1A 122.24(13) . . ?
C3A C2A C1A 116.0(4) . . ?
C3A C2A H2A 122.0 . . ?
C1A C2A H2A 122.0 . . ?
C2A C3A C4A 108.8(5) . . ?
C2A C3A H3A 125.6 . . ?
C4A C3A H3A 125.6 . . ?
C3A C4A S1A 113.6(4) . . ?
C3A C4A H4A 123.2 . . ?
S1A C4A H4A 123.2 . . ?
C1A S1A C4A 91.19(19) . . ?
C3B C2B H2B 123.6 . . ?
C4B C3B C2B 109.7(6) . . ?
C4B C3B H3B 125.2 . . ?
C2B C3B H3B 125.2 . . ?
C3B C4B S1B 114.7(4) . . ?
C3B C4B H4B 122.7 . . ?
S1B C4B H4B 122.7 . . ?
N1 C1 C2 123.91(15) . . ?
N1 C1 C6 117.02(14) . . ?
C2 C1 C6 119.05(14) . . ?
C1 C2 C3 119.44(15) . . ?
C1 C2 H2P 120.3 . . ?
C3 C2 H2P 120.3 . . ?
C2 C3 C4 117.11(14) . . ?
C2 C3 C1A 120.97(14) . . ?
C4 C3 C1A 121.91(15) . . ?
C5 C4 C3 118.95(15) . . ?
C5 C4 H4P 120.5 . . ?
C3 C4 H4P 120.5 . . ?
N1 C5 C4 124.24(15) . . ?
N1 C5 C9 116.25(14) . . ?
C4 C5 C9 119.45(15) . . ?
N2 C6 O1 119.34(16) . . ?
N2 C6 C1 123.93(15) . . ?
O1 C6 C1 116.67(15) . . ?
O1 C7 C8 104.13(16) . . ?
O1 C7 H7A 110.9 . . ?
C8 C7 H7A 110.9 . . ?
O1 C7 H7B 110.9 . . ?
C8 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
N2 C8 C7 104.75(15) . . ?
N2 C8 H8B 110.8 . . ?
C7 C8 H8B 110.8 . . ?
N2 C8 H8A 110.8 . . ?
C7 C8 H8A 110.8 . . ?
H8B C8 H8A 108.9 . . ?
N3 C9 O2 119.80(15) . . ?
N3 C9 C5 124.43(16) . . ?
O2 C9 C5 115.77(15) . . ?
O2 C10 C11 103.76(15) . . ?
O2 C10 H10B 111.0 . . ?
C11 C10 H10B 111.0 . . ?
O2 C10 H10A 111.0 . . ?
C11 C10 H10A 111.0 . . ?
H10B C10 H10A 109.0 . . ?
N3 C11 C10 105.21(15) . . ?
N3 C11 H11A 110.7 . . ?
C10 C11 H11A 110.7 . . ?
N3 C11 H11B 110.7 . . ?
C10 C11 H11B 110.7 . . ?
H11A C11 H11B 108.8 . . ?
C5 N1 C1 116.35(14) . . ?
C6 N2 C8 106.13(15) . . ?
C9 N3 C11 105.43(16) . . ?
C6 O1 C7 105.31(14) . . ?
C9 O2 C10 105.51(16) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.887
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.072
