# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2010
data_global
#TrackingRef '- is_g104_sd047_sm285.cif'
_journal_coden_Cambridge 177
#==============================================================================
_publ_contact_author_name 'Peter Langer'
_publ_contact_author_address
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
;
loop_
_publ_author_name
_publ_author_address
'Satenik Mkrtchyan'
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
;
'Viktor O. Iaroshenko'
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
National Taras Shevchenko University
62 Volodymyrska st.
Kyiv-33, 01033
Ukraine
;
'Sergii Dudkin'
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
;
'Ashot Gevorgyan'
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
;
'Marcelo Vilches-Herrera'
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
;
'Gagik Ghazaryan'
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
;
'Dmitro Volochnyuk'
;
National Taras Shevchenko University
62 Volodymyrska st.
Kyiv-33, 01033
Ukraine
Enamine Ltd.
23 A. Matrosova st.
01103 Kyiv
Ukraine
;
'Dmytro Ostrovskyi'
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
;
'Zeeshan Ahmed'
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
;
'Vyacheslav Ya. Sosnovskikh'
;
Department of Chemistry
Ural State University
620083 Ekaterinburg
Russian Federation
;
'Alexander Villinger'
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Anorganische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
;
'Peter Langer'
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
Leibniz-Institut f\"ur Katalyse an
der Universit\"at Rostock e.V.
Albert-Einstein-Strasse 29a
18059 Rostock
Bundesrepublik Deutschland
;
_publ_contact_author_email peter.langer@uni-rostock.de
_publ_contact_author_fax '+49 (0)381/498-6410'
_publ_contact_author_phone '+49 (0)381/498-6412'
_publ_requested_journal OBC
_publ_section_title
;
3-Methoxalylchromone - A Novel Versatile Reagent for the Regioselective
Purine Isostere Synthesis
;
#=============================================================================
data_is_g104
_database_code_depnum_ccdc_archive 'CCDC 783350'
#TrackingRef '- is_g104_sd047_sm285.cif'
_audit_author_name 'Villinger, A.'
_audit_creation_method SHELXL-97
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C12 H8 O5'
_chemical_formula_sum 'C12 H8 O5'
_chemical_formula_weight 232.18
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_space_group_name_Hall '-P 2yn'
_symmetry_Int_Tables_number 14
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 10.4760(8)
_cell_length_b 6.7599(5)
_cell_length_c 14.5944(10)
_cell_angle_alpha 90.00
_cell_angle_beta 93.438(4)
_cell_angle_gamma 90.00
_cell_volume 1031.67(13)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 2224
_cell_measurement_theta_min 4.929
_cell_measurement_theta_max 53.578
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 1.00
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.04
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.495
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 480
_exptl_absorpt_coefficient_mu 0.118
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.8907
_exptl_absorpt_correction_T_max 0.9953
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method 'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 10806
_diffrn_reflns_av_R_equivalents 0.0355
_diffrn_reflns_av_sigmaI/netI 0.0431
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -6
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_limit_l_max 20
_diffrn_reflns_theta_min 2.33
_diffrn_reflns_theta_max 29.92
_reflns_number_total 2982
_reflns_number_gt 1868
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Bruker Apex v2.0-2'
_computing_cell_refinement 'Bruker Apex v2.0-2'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material SHELXL-97
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms were positioned geometrically and refined using a
riding model , with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) =
1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times
U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0720P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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 2982
_refine_ls_number_parameters 155
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0946
_refine_ls_R_factor_gt 0.0494
_refine_ls_wR_factor_ref 0.1368
_refine_ls_wR_factor_gt 0.1225
_refine_ls_goodness_of_fit_ref 1.011
_refine_ls_restrained_S_all 1.011
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.10120(11) -0.44385(16) 0.69318(7) 0.0302(3) Uani 1 1 d . . .
O2 O 0.11329(11) 0.09810(16) 0.56780(7) 0.0282(3) Uani 1 1 d . . .
O3 O 0.15225(14) -0.39750(19) 0.41281(8) 0.0438(3) Uani 1 1 d . . .
O4 O 0.34455(11) -0.02913(19) 0.46591(7) 0.0377(3) Uani 1 1 d . . .
O5 O 0.18696(12) 0.00107(18) 0.35402(7) 0.0346(3) Uani 1 1 d . . .
C1 C 0.12179(16) -0.4255(2) 0.60366(10) 0.0273(4) Uani 1 1 d . . .
H1 H 0.1294 -0.5432 0.5688 0.033 Uiso 1 1 calc R . .
C2 C 0.13237(14) -0.2505(2) 0.55975(9) 0.0239(3) Uani 1 1 d . . .
C3 C 0.11412(14) -0.0639(2) 0.60692(9) 0.0212(3) Uani 1 1 d . . .
C4 C 0.09575(14) -0.0853(2) 0.70638(9) 0.0219(3) Uani 1 1 d . . .
C5 C 0.09152(14) -0.2730(2) 0.74491(10) 0.0243(3) Uani 1 1 d . . .
C6 C 0.07683(15) -0.3018(3) 0.83857(10) 0.0321(4) Uani 1 1 d . . .
H6 H 0.0756 -0.4311 0.8640 0.039 Uiso 1 1 calc R . .
C7 C 0.06415(17) -0.1372(3) 0.89283(10) 0.0346(4) Uani 1 1 d . . .
H7 H 0.0541 -0.1535 0.9567 0.041 Uiso 1 1 calc R . .
C8 C 0.06582(17) 0.0529(3) 0.85584(10) 0.0332(4) Uani 1 1 d . . .
H8 H 0.0562 0.1646 0.8943 0.040 Uiso 1 1 calc R . .
C9 C 0.08145(15) 0.0789(2) 0.76299(10) 0.0265(4) Uani 1 1 d . . .
H9 H 0.0824 0.2085 0.7378 0.032 Uiso 1 1 calc R . .
C10 C 0.16650(15) -0.2546(2) 0.46289(10) 0.0282(4) Uani 1 1 d . . .
C11 C 0.24251(16) -0.0761(2) 0.42974(10) 0.0285(4) Uani 1 1 d . . .
C12 C 0.25345(19) 0.1647(3) 0.31280(13) 0.0457(5) Uani 1 1 d . . .
H12A H 0.2625 0.2741 0.3567 0.068 Uiso 1 1 calc R . .
H12B H 0.2042 0.2093 0.2574 0.068 Uiso 1 1 calc R . .
H12C H 0.3383 0.1208 0.2965 0.068 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0482(7) 0.0160(6) 0.0262(5) 0.0048(4) 0.0017(5) -0.0017(5)
O2 0.0444(7) 0.0160(5) 0.0244(5) 0.0047(4) 0.0050(5) 0.0024(5)
O3 0.0704(9) 0.0291(7) 0.0327(6) -0.0100(5) 0.0099(6) -0.0055(7)
O4 0.0331(7) 0.0461(8) 0.0333(6) -0.0068(5) -0.0019(5) -0.0014(6)
O5 0.0402(7) 0.0363(7) 0.0271(5) 0.0070(5) 0.0010(5) -0.0048(6)
C1 0.0381(9) 0.0170(8) 0.0267(7) -0.0007(6) 0.0012(6) 0.0007(7)
C2 0.0303(8) 0.0187(8) 0.0227(7) 0.0005(6) 0.0007(6) 0.0015(6)
C3 0.0246(8) 0.0158(7) 0.0230(6) 0.0018(6) 0.0010(6) 0.0004(6)
C4 0.0252(8) 0.0201(8) 0.0202(6) 0.0038(6) 0.0011(5) -0.0005(6)
C5 0.0289(8) 0.0190(8) 0.0249(7) 0.0017(6) 0.0005(6) 0.0000(6)
C6 0.0403(10) 0.0281(9) 0.0279(8) 0.0109(7) 0.0030(7) -0.0011(7)
C7 0.0447(10) 0.0395(11) 0.0199(7) 0.0041(7) 0.0053(6) -0.0006(8)
C8 0.0440(10) 0.0305(10) 0.0258(7) -0.0039(7) 0.0070(7) -0.0004(8)
C9 0.0342(9) 0.0195(8) 0.0258(7) 0.0010(6) 0.0035(6) 0.0005(6)
C10 0.0371(9) 0.0228(9) 0.0246(7) -0.0017(6) 0.0014(6) 0.0043(7)
C11 0.0365(9) 0.0271(9) 0.0222(7) -0.0053(6) 0.0044(6) 0.0049(7)
C12 0.0530(12) 0.0366(11) 0.0485(11) 0.0119(9) 0.0126(9) -0.0058(9)
#==============================================================================
# MOLECULAR GEOMETRY
_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
O1 C1 1.3425(17) . ?
O1 C5 1.3867(18) . ?
O2 C3 1.2348(16) . ?
O3 C10 1.2151(19) . ?
O4 C11 1.206(2) . ?
O5 C11 1.3249(19) . ?
O5 C12 1.456(2) . ?
C1 C2 1.353(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.455(2) . ?
C2 C10 1.479(2) . ?
C3 C4 1.4827(18) . ?
C4 C5 1.390(2) . ?
C4 C9 1.397(2) . ?
C5 C6 1.398(2) . ?
C6 C7 1.377(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.395(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.539(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C5 118.31(12) . . ?
C11 O5 C12 116.53(14) . . ?
O1 C1 C2 124.34(14) . . ?
O1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C1 C2 C3 121.13(13) . . ?
C1 C2 C10 117.88(13) . . ?
C3 C2 C10 120.96(13) . . ?
O2 C3 C2 123.20(12) . . ?
O2 C3 C4 122.79(13) . . ?
C2 C3 C4 114.02(12) . . ?
C5 C4 C9 118.62(13) . . ?
C5 C4 C3 119.63(13) . . ?
C9 C4 C3 121.75(13) . . ?
O1 C5 C4 122.33(12) . . ?
O1 C5 C6 115.61(13) . . ?
C4 C5 C6 122.05(14) . . ?
C7 C6 C5 118.03(15) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C6 C7 C8 121.22(14) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 120.03(15) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C4 120.04(14) . . ?
C8 C9 H9 120.0 . . ?
C4 C9 H9 120.0 . . ?
O3 C10 C2 124.17(15) . . ?
O3 C10 C11 118.77(13) . . ?
C2 C10 C11 116.42(13) . . ?
O4 C11 O5 126.50(16) . . ?
O4 C11 C10 122.04(14) . . ?
O5 C11 C10 111.17(14) . . ?
O5 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 C2 -0.8(2) . . . . ?
O1 C1 C2 C3 -3.7(3) . . . . ?
O1 C1 C2 C10 174.65(14) . . . . ?
C1 C2 C3 O2 -174.33(15) . . . . ?
C10 C2 C3 O2 7.3(2) . . . . ?
C1 C2 C3 C4 5.3(2) . . . . ?
C10 C2 C3 C4 -173.02(13) . . . . ?
O2 C3 C4 C5 176.83(14) . . . . ?
C2 C3 C4 C5 -2.8(2) . . . . ?
O2 C3 C4 C9 -2.7(2) . . . . ?
C2 C3 C4 C9 177.68(14) . . . . ?
C1 O1 C5 C4 3.4(2) . . . . ?
C1 O1 C5 C6 -176.76(14) . . . . ?
C9 C4 C5 O1 178.11(14) . . . . ?
C3 C4 C5 O1 -1.4(2) . . . . ?
C9 C4 C5 C6 -1.7(2) . . . . ?
C3 C4 C5 C6 178.77(14) . . . . ?
O1 C5 C6 C7 -178.71(14) . . . . ?
C4 C5 C6 C7 1.1(2) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C7 C8 C9 C4 -0.1(3) . . . . ?
C5 C4 C9 C8 1.2(2) . . . . ?
C3 C4 C9 C8 -179.32(15) . . . . ?
C1 C2 C10 O3 20.8(3) . . . . ?
C3 C2 C10 O3 -160.76(16) . . . . ?
C1 C2 C10 C11 -149.85(15) . . . . ?
C3 C2 C10 C11 28.5(2) . . . . ?
C12 O5 C11 O4 -2.9(2) . . . . ?
C12 O5 C11 C10 -176.76(13) . . . . ?
O3 C10 C11 O4 -113.06(18) . . . . ?
C2 C10 C11 O4 58.2(2) . . . . ?
O3 C10 C11 O5 61.2(2) . . . . ?
C2 C10 C11 O5 -127.63(14) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 29.92
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.321
_refine_diff_density_min -0.206
_refine_diff_density_rms 0.053
#=============================================================================
data_is_sd047
_database_code_depnum_ccdc_archive 'CCDC 783351'
#TrackingRef '- is_g104_sd047_sm285.cif'
_audit_author_name 'Villinger, A.'
_audit_creation_method SHELXL-97
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety '2(C25 H19 N3 O5), C3 H7 N O'
_chemical_formula_sum 'C26.50 H22.50 N3.50 O5.50'
_chemical_formula_weight 477.98
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'
#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'C 2/c'
_symmetry_space_group_name_Hall '-C 2yc'
_symmetry_Int_Tables_number 15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 12.244(9)
_cell_length_b 14.288(10)
_cell_length_c 26.562(19)
_cell_angle_alpha 90.00
_cell_angle_beta 95.317(13)
_cell_angle_gamma 90.00
_cell_volume 4627(6)
_cell_formula_units_Z 8
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 2621
_cell_measurement_theta_min 4.763
_cell_measurement_theta_max 47.038
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.27
_exptl_crystal_size_mid 0.26
_exptl_crystal_size_min 0.04
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.372
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 2000
_exptl_absorpt_coefficient_mu 0.098
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9741
_exptl_absorpt_correction_T_max 0.9961
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method 'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 21990
_diffrn_reflns_av_R_equivalents 0.0592
_diffrn_reflns_av_sigmaI/netI 0.0790
_diffrn_reflns_limit_h_min -16
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_l_min -34
_diffrn_reflns_limit_l_max 35
_diffrn_reflns_theta_min 2.20
_diffrn_reflns_theta_max 28.00
_reflns_number_total 5597
_reflns_number_gt 3081
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Bruker Apex v2.0-2'
_computing_cell_refinement 'Bruker Apex v2.0-2'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material SHELXL-97
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms were positioned geometrically and refined using a
riding model , with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) =
1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times
U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0440P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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 5597
_refine_ls_number_parameters 351
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1177
_refine_ls_R_factor_gt 0.0490
_refine_ls_wR_factor_ref 0.1039
_refine_ls_wR_factor_gt 0.0892
_refine_ls_goodness_of_fit_ref 0.954
_refine_ls_restrained_S_all 0.954
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.02248(12) 0.76001(10) 0.52624(5) 0.0270(3) Uani 1 1 d . . .
N2 N 0.08941(12) 0.60191(9) 0.52540(5) 0.0249(3) Uani 1 1 d . . .
N3 N 0.15723(14) 0.93686(12) 0.39314(7) 0.0482(5) Uani 1 1 d . . .
O1 O 0.23741(11) 0.86234(9) 0.74822(5) 0.0397(4) Uani 1 1 d . . .
O2 O 0.21413(12) 0.38600(9) 0.49910(5) 0.0427(4) Uani 1 1 d . . .
O3 O 0.12032(10) 0.43193(8) 0.56348(4) 0.0320(3) Uani 1 1 d . . .
O4 O 0.36789(10) 0.49245(8) 0.44252(4) 0.0317(3) Uani 1 1 d . . .
O5 O 0.38369(11) 0.36502(9) 0.37438(5) 0.0349(3) Uani 1 1 d . . .
C1 C 0.03379(15) 0.83776(12) 0.49749(7) 0.0289(4) Uani 1 1 d . . .
H1 H 0.0017 0.8969 0.5033 0.035 Uiso 1 1 calc R . .
C2 C 0.09825(14) 0.81893(12) 0.45871(7) 0.0265(4) Uani 1 1 d . . .
C3 C 0.12964(14) 0.72227(11) 0.46359(6) 0.0235(4) Uani 1 1 d . . .
C4 C 0.08161(14) 0.68810(11) 0.50662(6) 0.0237(4) Uani 1 1 d . . .
C5 C 0.18997(14) 0.65901(11) 0.43775(6) 0.0239(4) Uani 1 1 d . . .
H5 H 0.2230 0.6772 0.4083 0.029 Uiso 1 1 calc R . .
C6 C 0.20045(14) 0.56816(11) 0.45630(6) 0.0225(4) Uani 1 1 d . . .
C7 C 0.14982(14) 0.54281(11) 0.49989(6) 0.0233(4) Uani 1 1 d . . .
C8 C 0.13021(15) 0.88472(13) 0.42247(7) 0.0311(4) Uani 1 1 d . . .
C9 C -0.03491(15) 0.75513(13) 0.57260(7) 0.0322(4) Uani 1 1 d . . .
H9A H -0.0597 0.6900 0.5774 0.039 Uiso 1 1 calc R . .
H9B H -0.1008 0.7956 0.5685 0.039 Uiso 1 1 calc R . .
C10 C 0.03674(15) 0.78559(12) 0.61908(6) 0.0273(4) Uani 1 1 d . . .
C11 C 0.01932(16) 0.87092(12) 0.64229(7) 0.0311(4) Uani 1 1 d . . .
H11 H -0.0382 0.9105 0.6285 0.037 Uiso 1 1 calc R . .
C12 C 0.08459(16) 0.89967(13) 0.68554(7) 0.0316(4) Uani 1 1 d . . .
H12 H 0.0716 0.9582 0.7009 0.038 Uiso 1 1 calc R . .
C13 C 0.16867(15) 0.84175(13) 0.70580(6) 0.0291(4) Uani 1 1 d . . .
C14 C 0.18721(15) 0.75641(12) 0.68263(7) 0.0305(4) Uani 1 1 d . . .
H14 H 0.2451 0.7171 0.6963 0.037 Uiso 1 1 calc R . .
C15 C 0.12247(15) 0.72845(12) 0.64001(7) 0.0302(4) Uani 1 1 d . . .
H15 H 0.1360 0.6700 0.6247 0.036 Uiso 1 1 calc R . .
C16 C 0.21981(19) 0.94898(14) 0.77359(7) 0.0462(6) Uani 1 1 d . . .
H16A H 0.1441 0.9515 0.7827 0.069 Uiso 1 1 calc R . .
H16B H 0.2329 1.0014 0.7511 0.069 Uiso 1 1 calc R . .
H16C H 0.2705 0.9532 0.8043 0.069 Uiso 1 1 calc R . .
C17 C 0.16529(15) 0.44575(12) 0.52027(6) 0.0266(4) Uani 1 1 d . . .
C18 C 0.14149(17) 0.34089(13) 0.58651(7) 0.0400(5) Uani 1 1 d . . .
H18A H 0.2162 0.3394 0.6033 0.060 Uiso 1 1 calc R . .
H18B H 0.1336 0.2924 0.5603 0.060 Uiso 1 1 calc R . .
H18C H 0.0889 0.3294 0.6115 0.060 Uiso 1 1 calc R . .
C19 C 0.26878(15) 0.50063(11) 0.42865(6) 0.0243(4) Uani 1 1 d . . .
C20 C 0.21749(14) 0.45200(11) 0.38402(6) 0.0222(4) Uani 1 1 d . . .
C21 C 0.10814(15) 0.46920(12) 0.36518(7) 0.0292(4) Uani 1 1 d . . .
H21 H 0.0662 0.5138 0.3816 0.035 Uiso 1 1 calc R . .
C22 C 0.06063(16) 0.42248(13) 0.32322(7) 0.0343(5) Uani 1 1 d . . .
H22 H -0.0126 0.4361 0.3103 0.041 Uiso 1 1 calc R . .
C23 C 0.12085(16) 0.35543(13) 0.30007(7) 0.0357(5) Uani 1 1 d . . .
H23 H 0.0878 0.3222 0.2716 0.043 Uiso 1 1 calc R . .
C24 C 0.22812(16) 0.33633(13) 0.31777(7) 0.0323(4) Uani 1 1 d . . .
H24 H 0.2681 0.2897 0.3018 0.039 Uiso 1 1 calc R . .
C25 C 0.27755(15) 0.38514(12) 0.35892(6) 0.0256(4) Uani 1 1 d . . .
H5A H 0.4050(18) 0.4060(15) 0.4021(8) 0.061(7) Uiso 1 1 d . . .
C26 C 0.4878(4) 0.3421(3) 0.22928(18) 0.0433(12) Uani 0.50 1 d P . .
C27 C 0.4772(8) 0.1786(5) 0.2024(4) 0.055(2) Uani 0.50 1 d P . .
H27A H 0.5419 0.1380 0.2040 0.082 Uiso 0.50 1 calc PR . .
H27B H 0.4662 0.2078 0.1689 0.082 Uiso 0.50 1 calc PR . .
H27C H 0.4125 0.1413 0.2084 0.082 Uiso 0.50 1 calc PR . .
C28 C 0.5073(7) 0.2199(5) 0.2932(3) 0.0443(17) Uani 0.50 1 d P . .
H28A H 0.5737 0.1815 0.2987 0.066 Uiso 0.50 1 calc PR . .
H28B H 0.4435 0.1828 0.3007 0.066 Uiso 0.50 1 calc PR . .
H28C H 0.5142 0.2746 0.3156 0.066 Uiso 0.50 1 calc PR . .
N4 N 0.4934(13) 0.2508(2) 0.2407(2) 0.0338(17) Uani 0.50 1 d P . .
O6 O 0.5000 0.40644(19) 0.2500 0.0862(9) Uani 1 2 d S . .
H26 H 0.476(3) 0.351(3) 0.1959(16) 0.049(13) Uiso 0.50 1 d P . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0299(9) 0.0221(8) 0.0289(8) -0.0022(6) 0.0024(7) 0.0032(7)
N2 0.0262(9) 0.0225(8) 0.0258(8) 0.0002(6) 0.0008(6) 0.0003(6)
N3 0.0419(12) 0.0411(11) 0.0609(12) 0.0204(9) 0.0009(9) 0.0028(8)
O1 0.0469(9) 0.0390(8) 0.0321(7) -0.0001(6) -0.0021(7) 0.0037(6)
O2 0.0650(10) 0.0233(7) 0.0425(8) 0.0039(6) 0.0189(7) 0.0113(7)
O3 0.0392(8) 0.0269(7) 0.0309(7) 0.0084(5) 0.0088(6) 0.0034(6)
O4 0.0262(8) 0.0314(7) 0.0367(7) -0.0048(6) -0.0024(6) 0.0033(6)
O5 0.0283(8) 0.0378(8) 0.0377(8) -0.0097(6) -0.0018(6) 0.0091(6)
C1 0.0278(11) 0.0204(10) 0.0366(11) -0.0020(8) -0.0071(9) 0.0036(8)
C2 0.0256(11) 0.0197(9) 0.0330(10) 0.0005(8) -0.0040(8) 0.0003(8)
C3 0.0217(10) 0.0211(9) 0.0267(9) 0.0006(7) -0.0029(8) -0.0006(7)
C4 0.0234(10) 0.0216(10) 0.0254(9) -0.0024(7) -0.0014(8) 0.0017(7)
C5 0.0210(10) 0.0261(10) 0.0243(9) 0.0007(7) 0.0004(7) -0.0019(7)
C6 0.0236(10) 0.0213(9) 0.0223(9) -0.0011(7) -0.0001(7) -0.0012(7)
C7 0.0225(10) 0.0205(9) 0.0266(9) -0.0008(7) 0.0011(8) 0.0000(7)
C8 0.0278(11) 0.0217(10) 0.0426(11) 0.0046(9) -0.0031(9) 0.0034(8)
C9 0.0252(11) 0.0347(11) 0.0376(11) -0.0030(8) 0.0086(9) 0.0053(8)
C10 0.0286(11) 0.0259(10) 0.0283(10) 0.0012(8) 0.0087(8) -0.0002(8)
C11 0.0335(12) 0.0269(10) 0.0335(11) 0.0020(8) 0.0060(9) 0.0061(8)
C12 0.0404(12) 0.0236(10) 0.0318(10) -0.0001(8) 0.0080(9) 0.0037(8)
C13 0.0347(12) 0.0277(11) 0.0257(10) 0.0055(8) 0.0069(9) -0.0030(8)
C14 0.0295(11) 0.0293(11) 0.0337(10) 0.0075(8) 0.0084(9) 0.0051(8)
C15 0.0337(12) 0.0250(10) 0.0335(10) 0.0017(8) 0.0123(9) 0.0027(8)
C16 0.0552(15) 0.0424(13) 0.0403(12) -0.0086(10) 0.0004(11) -0.0010(11)
C17 0.0275(11) 0.0267(10) 0.0254(10) 0.0010(8) 0.0018(8) -0.0004(8)
C18 0.0472(14) 0.0341(12) 0.0393(12) 0.0174(9) 0.0068(10) 0.0049(10)
C19 0.0274(11) 0.0197(9) 0.0258(9) 0.0033(7) 0.0031(8) -0.0006(8)
C20 0.0234(10) 0.0214(9) 0.0220(9) 0.0015(7) 0.0028(7) -0.0018(7)
C21 0.0257(11) 0.0292(10) 0.0328(10) -0.0020(8) 0.0023(8) 0.0007(8)
C22 0.0258(11) 0.0414(12) 0.0344(11) -0.0028(9) -0.0042(9) -0.0006(9)
C23 0.0395(13) 0.0377(12) 0.0290(10) -0.0072(8) -0.0010(9) -0.0026(9)
C24 0.0367(12) 0.0311(11) 0.0293(10) -0.0075(8) 0.0049(9) 0.0023(9)
C25 0.0283(11) 0.0243(10) 0.0246(9) 0.0028(7) 0.0038(8) 0.0001(8)
C26 0.049(3) 0.044(3) 0.039(3) 0.000(2) 0.015(3) -0.008(2)
C27 0.053(5) 0.060(5) 0.054(3) -0.016(5) 0.021(3) -0.006(4)
C28 0.040(4) 0.047(5) 0.047(4) -0.004(4) 0.011(3) 0.005(4)
N4 0.050(4) 0.0357(18) 0.019(5) -0.0035(17) 0.019(6) -0.003(2)
O6 0.086(2) 0.0374(16) 0.137(3) 0.000 0.0221(19) 0.000
#==============================================================================
# MOLECULAR GEOMETRY
_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
N1 C1 1.362(2) . ?
N1 C4 1.386(2) . ?
N1 C9 1.475(2) . ?
N2 C4 1.329(2) . ?
N2 C7 1.346(2) . ?
N3 C8 1.149(2) . ?
O1 C13 1.374(2) . ?
O1 C16 1.435(2) . ?
O2 C17 1.210(2) . ?
O3 C17 1.333(2) . ?
O3 C18 1.451(2) . ?
O4 C19 1.241(2) . ?
O5 C25 1.357(2) . ?
O5 H5A 0.96(2) . ?
C1 C2 1.381(3) . ?
C1 H1 0.9500 . ?
C2 C8 1.426(3) . ?
C2 C3 1.436(2) . ?
C3 C5 1.388(2) . ?
C3 C4 1.420(2) . ?
C5 C6 1.390(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.410(2) . ?
C6 C19 1.512(2) . ?
C7 C17 1.494(2) . ?
C9 C10 1.511(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.391(2) . ?
C10 C15 1.403(3) . ?
C11 C12 1.399(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(3) . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.464(2) . ?
C20 C21 1.407(2) . ?
C20 C25 1.410(2) . ?
C21 C22 1.380(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(2) . ?
C24 H24 0.9500 . ?
C26 O6 1.075(4) . ?
C26 C26 1.113(10) 2_655 ?
C26 N4 1.339(5) . ?
C26 N4 1.534(6) 2_655 ?
C26 C28 1.848(8) 2_655 ?
C26 H26 0.89(4) . ?
C27 N4 1.450(9) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 N4 1.457(9) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N4 N4 0.503(12) 2_655 ?
N4 C28 1.004(10) 2_655 ?
N4 C26 1.534(6) 2_655 ?
N4 C27 1.837(10) 2_655 ?
O6 C26 1.075(4) 2_655 ?
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
C1 N1 C4 108.05(15) . . ?
C1 N1 C9 125.99(15) . . ?
C4 N1 C9 125.78(14) . . ?
C4 N2 C7 114.58(15) . . ?
C13 O1 C16 117.54(15) . . ?
C17 O3 C18 115.09(14) . . ?
C25 O5 H5A 106.8(13) . . ?
N1 C1 C2 110.74(16) . . ?
N1 C1 H1 124.6 . . ?
C2 C1 H1 124.6 . . ?
C1 C2 C8 125.92(16) . . ?
C1 C2 C3 106.66(15) . . ?
C8 C2 C3 127.38(17) . . ?
C5 C3 C4 116.95(15) . . ?
C5 C3 C2 137.02(17) . . ?
C4 C3 C2 106.03(15) . . ?
N2 C4 N1 124.59(16) . . ?
N2 C4 C3 126.89(15) . . ?
N1 C4 C3 108.51(14) . . ?
C3 C5 C6 117.93(16) . . ?
C3 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C5 C6 C7 119.85(15) . . ?
C5 C6 C19 117.44(15) . . ?
C7 C6 C19 122.70(15) . . ?
N2 C7 C6 123.78(15) . . ?
N2 C7 C17 117.18(15) . . ?
C6 C7 C17 119.03(15) . . ?
N3 C8 C2 179.0(2) . . ?
N1 C9 C10 112.53(16) . . ?
N1 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C15 118.29(18) . . ?
C11 C10 C9 120.88(17) . . ?
C15 C10 C9 120.83(16) . . ?
C10 C11 C12 121.45(18) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 119.30(17) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
O1 C13 C12 124.43(17) . . ?
O1 C13 C14 115.90(16) . . ?
C12 C13 C14 119.67(18) . . ?
C15 C14 C13 120.72(17) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C10 120.56(17) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 O3 123.84(17) . . ?
O2 C17 C7 122.53(17) . . ?
O3 C17 C7 113.63(15) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 C20 122.01(16) . . ?
O4 C19 C6 119.08(15) . . ?
C20 C19 C6 118.76(16) . . ?
C21 C20 C25 118.10(16) . . ?
C21 C20 C19 121.85(16) . . ?
C25 C20 C19 120.05(16) . . ?
C22 C21 C20 121.24(17) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C23 119.36(18) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C24 C23 C22 120.91(17) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 120.04(17) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
O5 C25 C24 117.87(16) . . ?
O5 C25 C20 121.82(16) . . ?
C24 C25 C20 120.29(17) . . ?
O6 C26 C26 58.8(3) . 2_655 ?
O6 C26 N4 135.6(5) . . ?
C26 C26 N4 76.8(3) 2_655 . ?
O6 C26 N4 117.0(5) . 2_655 ?
C26 C26 N4 58.2(3) 2_655 2_655 ?
N4 C26 N4 18.6(4) . 2_655 ?
O6 C26 C28 165.1(5) . 2_655 ?
C26 C26 C28 107.8(3) 2_655 2_655 ?
N4 C26 C28 31.9(4) . 2_655 ?
N4 C26 C28 50.0(3) 2_655 2_655 ?
O6 C26 H26 113(3) . . ?
C26 C26 H26 170(3) 2_655 . ?
N4 C26 H26 111(3) . . ?
N4 C26 H26 130(3) 2_655 . ?
C28 C26 H26 80(3) 2_655 . ?
N4 C27 H27A 109.5 . . ?
N4 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N4 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N4 C28 H28A 109.5 . . ?
N4 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N4 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N4 N4 C28 149(3) 2_655 2_655 ?
N4 N4 C26 103.1(4) 2_655 . ?
C28 N4 C26 103.2(6) 2_655 . ?
N4 N4 C27 134.2(7) 2_655 . ?
C28 N4 C27 21.0(7) 2_655 . ?
C26 N4 C27 122.1(6) . . ?
N4 N4 C28 21.0(17) 2_655 . ?
C28 N4 C28 135.7(8) 2_655 . ?
C26 N4 C28 120.8(5) . . ?
C27 N4 C28 116.9(4) . . ?
N4 N4 C26 58.2(3) 2_655 2_655 ?
C28 N4 C26 146.0(7) 2_655 2_655 ?
C26 N4 C26 45.0(4) . 2_655 ?
C27 N4 C26 166.7(6) . 2_655 ?
C28 N4 C26 76.3(4) . 2_655 ?
N4 N4 C27 34.5(5) 2_655 2_655 ?
C28 N4 C27 118.4(5) 2_655 2_655 ?
C26 N4 C27 137.4(5) . 2_655 ?
C27 N4 C27 100.5(7) . 2_655 ?
C28 N4 C27 17.5(5) . 2_655 ?
C26 N4 C27 92.4(5) 2_655 2_655 ?
C26 O6 C26 62.4(5) . 2_655 ?
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
C4 N1 C1 C2 0.7(2) . . . . ?
C9 N1 C1 C2 176.06(15) . . . . ?
N1 C1 C2 C8 -177.73(16) . . . . ?
N1 C1 C2 C3 0.0(2) . . . . ?
C1 C2 C3 C5 178.37(19) . . . . ?
C8 C2 C3 C5 -4.0(3) . . . . ?
C1 C2 C3 C4 -0.60(18) . . . . ?
C8 C2 C3 C4 177.04(17) . . . . ?
C7 N2 C4 N1 179.05(16) . . . . ?
C7 N2 C4 C3 -0.1(2) . . . . ?
C1 N1 C4 N2 179.70(16) . . . . ?
C9 N1 C4 N2 4.3(3) . . . . ?
C1 N1 C4 C3 -1.06(19) . . . . ?
C9 N1 C4 C3 -176.44(15) . . . . ?
C5 C3 C4 N2 1.0(3) . . . . ?
C2 C3 C4 N2 -179.76(17) . . . . ?
C5 C3 C4 N1 -178.19(14) . . . . ?
C2 C3 C4 N1 1.02(18) . . . . ?
C4 C3 C5 C6 -1.2(2) . . . . ?
C2 C3 C5 C6 179.95(18) . . . . ?
C3 C5 C6 C7 0.5(2) . . . . ?
C3 C5 C6 C19 -178.43(15) . . . . ?
C4 N2 C7 C6 -0.8(2) . . . . ?
C4 N2 C7 C17 177.74(15) . . . . ?
C5 C6 C7 N2 0.6(3) . . . . ?
C19 C6 C7 N2 179.40(16) . . . . ?
C5 C6 C7 C17 -177.90(15) . . . . ?
C19 C6 C7 C17 0.9(2) . . . . ?
C1 C2 C8 N3 159(13) . . . . ?
C3 C2 C8 N3 -18(13) . . . . ?
C1 N1 C9 C10 -83.6(2) . . . . ?
C4 N1 C9 C10 91.0(2) . . . . ?
N1 C9 C10 C11 107.33(19) . . . . ?
N1 C9 C10 C15 -72.8(2) . . . . ?
C15 C10 C11 C12 -0.3(3) . . . . ?
C9 C10 C11 C12 179.57(17) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C16 O1 C13 C12 0.9(3) . . . . ?
C16 O1 C13 C14 -179.07(16) . . . . ?
C11 C12 C13 O1 -179.58(16) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
O1 C13 C14 C15 179.51(15) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 C10 0.1(3) . . . . ?
C11 C10 C15 C14 0.3(3) . . . . ?
C9 C10 C15 C14 -179.63(16) . . . . ?
C18 O3 C17 O2 4.9(3) . . . . ?
C18 O3 C17 C7 -175.13(15) . . . . ?
N2 C7 C17 O2 176.79(17) . . . . ?
C6 C7 C17 O2 -4.6(3) . . . . ?
N2 C7 C17 O3 -3.1(2) . . . . ?
C6 C7 C17 O3 175.43(15) . . . . ?
C5 C6 C19 O4 91.8(2) . . . . ?
C7 C6 C19 O4 -87.0(2) . . . . ?
C5 C6 C19 C20 -83.8(2) . . . . ?
C7 C6 C19 C20 97.4(2) . . . . ?
O4 C19 C20 C21 -172.95(16) . . . . ?
C6 C19 C20 C21 2.5(2) . . . . ?
O4 C19 C20 C25 7.7(2) . . . . ?
C6 C19 C20 C25 -176.84(15) . . . . ?
C25 C20 C21 C22 -0.3(3) . . . . ?
C19 C20 C21 C22 -179.65(16) . . . . ?
C20 C21 C22 C23 1.8(3) . . . . ?
C21 C22 C23 C24 -1.4(3) . . . . ?
C22 C23 C24 C25 -0.7(3) . . . . ?
C23 C24 C25 O5 -178.88(16) . . . . ?
C23 C24 C25 C20 2.3(3) . . . . ?
C21 C20 C25 O5 179.41(15) . . . . ?
C19 C20 C25 O5 -1.2(2) . . . . ?
C21 C20 C25 C24 -1.8(2) . . . . ?
C19 C20 C25 C24 177.58(15) . . . . ?
O6 C26 N4 N4 -4(5) . . . 2_655 ?
C26 C26 N4 N4 -3(4) 2_655 . . 2_655 ?
C28 C26 N4 N4 163(5) 2_655 . . 2_655 ?
O6 C26 N4 C28 -166.7(8) . . . 2_655 ?
C26 C26 N4 C28 -166.0(14) 2_655 . . 2_655 ?
N4 C26 N4 C28 -163(5) 2_655 . . 2_655 ?
O6 C26 N4 C27 -176.7(8) . . . . ?
C26 C26 N4 C27 -175.9(15) 2_655 . . . ?
N4 C26 N4 C27 -173(5) 2_655 . . . ?
C28 C26 N4 C27 -9.9(9) 2_655 . . . ?
O6 C26 N4 C28 8(2) . . . . ?
C26 C26 N4 C28 9.2(12) 2_655 . . . ?
N4 C26 N4 C28 12(3) 2_655 . . . ?
C28 C26 N4 C28 175(2) 2_655 . . . ?
O6 C26 N4 C26 -0.7(9) . . . 2_655 ?
N4 C26 N4 C26 3(4) 2_655 . . 2_655 ?
C28 C26 N4 C26 166.0(14) 2_655 . . 2_655 ?
O6 C26 N4 C27 1(2) . . . 2_655 ?
C26 C26 N4 C27 1.7(16) 2_655 . . 2_655 ?
N4 C26 N4 C27 5(2) 2_655 . . 2_655 ?
C28 C26 N4 C27 168(3) 2_655 . . 2_655 ?
N4 C26 O6 C26 0.8(10) . . . 2_655 ?
N4 C26 O6 C26 -0.6(7) 2_655 . . 2_655 ?
C28 C26 O6 C26 -27.4(15) 2_655 . . 2_655 ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 28.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.200
_refine_diff_density_min -0.220
_refine_diff_density_rms 0.048
#=============================================================================
data_is_sm285
_database_code_depnum_ccdc_archive 'CCDC 783352'
#TrackingRef '- is_g104_sd047_sm285.cif'
_audit_author_name 'Villinger, A.'
_audit_creation_method SHELXL-97
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C17 H15 N3 O4 S'
_chemical_formula_sum 'C17 H15 N3 O4 S'
_chemical_formula_weight 357.38
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'
#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_Int_Tables_number 14
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 15.5148(4)
_cell_length_b 8.3533(2)
_cell_length_c 12.6393(3)
_cell_angle_alpha 90.00
_cell_angle_beta 98.6610(10)
_cell_angle_gamma 90.00
_cell_volume 1619.37(7)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 7769
_cell_measurement_theta_min 5.553
_cell_measurement_theta_max 60.018
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.44
_exptl_crystal_size_mid 0.42
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.466
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 744
_exptl_absorpt_coefficient_mu 0.229
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9061
_exptl_absorpt_correction_T_max 0.9819
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method 'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 17166
_diffrn_reflns_av_R_equivalents 0.0223
_diffrn_reflns_av_sigmaI/netI 0.0239
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 21
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 2.66
_diffrn_reflns_theta_max 30.00
_reflns_number_total 4697
_reflns_number_gt 3884
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Bruker Apex v2.0-2'
_computing_cell_refinement 'Bruker Apex v2.0-2'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material SHELXL-97
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms were positioned geometrically and refined using a
riding model , with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) =
1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times
U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0577P)^2^+0.3579P] where P=(Fo^2^+2Fc^2^)/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 4697
_refine_ls_number_parameters 233
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0480
_refine_ls_R_factor_gt 0.0377
_refine_ls_wR_factor_ref 0.1068
_refine_ls_wR_factor_gt 0.1017
_refine_ls_goodness_of_fit_ref 1.059
_refine_ls_restrained_S_all 1.059
_refine_ls_shift/su_max 0.003
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.99847(7) 0.24820(14) 1.09821(8) 0.0245(2) Uani 1 1 d . . .
N2 N 0.86445(6) 0.11616(13) 1.04315(8) 0.0222(2) Uani 1 1 d . . .
N3 N 1.12860(7) 0.39337(15) 1.10863(9) 0.0288(2) Uani 1 1 d . . .
O1 O 0.69203(6) -0.12374(12) 0.92851(8) 0.0315(2) Uani 1 1 d . . .
O2 O 0.70705(6) 0.01812(12) 1.08099(8) 0.0301(2) Uani 1 1 d . . .
O3 O 0.76386(6) -0.02370(14) 0.68650(8) 0.0363(2) Uani 1 1 d . . .
O4 O 0.61708(7) 0.02935(14) 0.57107(8) 0.0344(2) Uani 1 1 d . . .
S1 S 1.04782(2) 0.31529(4) 0.91214(2) 0.02542(10) Uani 1 1 d . . .
C1 C 1.06018(8) 0.31867(15) 1.05381(10) 0.0226(2) Uani 1 1 d . . .
C2 C 0.93569(8) 0.19007(14) 1.01977(9) 0.0208(2) Uani 1 1 d . . .
C3 C 0.95029(8) 0.21473(15) 0.91238(10) 0.0221(2) Uani 1 1 d . . .
C4 C 0.88896(8) 0.16809(16) 0.82779(10) 0.0246(2) Uani 1 1 d . . .
H4 H 0.8979 0.1837 0.7558 0.030 Uiso 1 1 calc R . .
C5 C 0.81273(8) 0.09665(15) 0.85232(9) 0.0224(2) Uani 1 1 d . . .
C6 C 0.80543(7) 0.07057(15) 0.96024(9) 0.0213(2) Uani 1 1 d . . .
C7 C 0.72896(7) -0.02297(15) 0.98693(10) 0.0229(2) Uani 1 1 d . . .
C8 C 0.63549(10) -0.0711(2) 1.11300(13) 0.0390(3) Uani 1 1 d . . .
H8A H 0.5828 -0.0533 1.0610 0.058 Uiso 1 1 calc R . .
H8B H 0.6254 -0.0350 1.1839 0.058 Uiso 1 1 calc R . .
H8C H 0.6498 -0.1854 1.1158 0.058 Uiso 1 1 calc R . .
C9 C 0.74345(8) 0.06053(15) 0.75911(10) 0.0238(2) Uani 1 1 d . . .
C10 C 0.65721(8) 0.13689(14) 0.74924(9) 0.0209(2) Uani 1 1 d . . .
C11 C 0.59796(8) 0.11804(15) 0.65392(9) 0.0244(2) Uani 1 1 d . . .
C12 C 0.51603(9) 0.19055(16) 0.64238(11) 0.0288(3) Uani 1 1 d . . .
H12 H 0.4767 0.1785 0.5776 0.035 Uiso 1 1 calc R . .
C13 C 0.49212(9) 0.27965(17) 0.72509(11) 0.0295(3) Uani 1 1 d . . .
H13 H 0.4361 0.3279 0.7171 0.035 Uiso 1 1 calc R . .
C14 C 0.54937(9) 0.29955(16) 0.82030(11) 0.0277(3) Uani 1 1 d . . .
H14 H 0.5322 0.3598 0.8773 0.033 Uiso 1 1 calc R . .
C15 C 0.63104(8) 0.23124(15) 0.83116(10) 0.0231(2) Uani 1 1 d . . .
H15 H 0.6706 0.2481 0.8953 0.028 Uiso 1 1 calc R . .
C16 C 1.19771(8) 0.46048(17) 1.05655(11) 0.0302(3) Uani 1 1 d . . .
H16A H 1.1843 0.4426 0.9792 0.045 Uiso 1 1 calc R . .
H16B H 1.2531 0.4084 1.0844 0.045 Uiso 1 1 calc R . .
H16C H 1.2023 0.5757 1.0709 0.045 Uiso 1 1 calc R . .
C17 C 1.13652(10) 0.4045(2) 1.22473(11) 0.0381(3) Uani 1 1 d . . .
H17A H 1.0788 0.4219 1.2452 0.057 Uiso 1 1 calc R . .
H17B H 1.1748 0.4943 1.2501 0.057 Uiso 1 1 calc R . .
H17C H 1.1613 0.3048 1.2570 0.057 Uiso 1 1 calc R . .
H1 H 0.6694(15) -0.003(3) 0.5914(18) 0.065(7) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0216(5) 0.0300(6) 0.0214(5) 0.0018(4) 0.0021(4) -0.0048(4)
N2 0.0199(5) 0.0263(5) 0.0200(5) 0.0043(4) 0.0014(4) -0.0014(4)
N3 0.0252(5) 0.0375(6) 0.0235(5) 0.0003(4) 0.0035(4) -0.0107(5)
O1 0.0299(5) 0.0298(5) 0.0337(5) -0.0023(4) 0.0009(4) -0.0069(4)
O2 0.0260(4) 0.0363(5) 0.0294(5) -0.0018(4) 0.0084(4) -0.0085(4)
O3 0.0306(5) 0.0500(6) 0.0276(5) -0.0146(4) 0.0020(4) 0.0076(5)
O4 0.0353(5) 0.0440(6) 0.0214(5) -0.0097(4) -0.0036(4) 0.0041(5)
S1 0.02305(15) 0.03264(18) 0.02217(16) -0.00272(12) 0.00857(11) -0.00415(12)
C1 0.0220(5) 0.0241(6) 0.0218(6) 0.0000(4) 0.0036(4) -0.0007(4)
C2 0.0201(5) 0.0228(6) 0.0194(5) 0.0020(4) 0.0021(4) 0.0010(4)
C3 0.0202(5) 0.0256(6) 0.0213(6) -0.0003(4) 0.0059(4) 0.0003(4)
C4 0.0243(6) 0.0304(6) 0.0197(6) -0.0020(5) 0.0052(4) 0.0015(5)
C5 0.0214(5) 0.0252(6) 0.0198(5) -0.0022(4) 0.0007(4) 0.0016(4)
C6 0.0192(5) 0.0223(5) 0.0219(6) 0.0014(4) 0.0019(4) 0.0006(4)
C7 0.0198(5) 0.0243(6) 0.0237(6) 0.0047(5) 0.0000(4) 0.0015(4)
C8 0.0319(7) 0.0431(8) 0.0453(9) -0.0006(7) 0.0166(6) -0.0107(6)
C9 0.0234(6) 0.0278(6) 0.0196(5) -0.0016(5) 0.0015(4) 0.0003(5)
C10 0.0215(5) 0.0216(5) 0.0190(5) 0.0000(4) 0.0007(4) -0.0007(4)
C11 0.0278(6) 0.0250(6) 0.0191(5) 0.0000(4) -0.0006(5) -0.0024(5)
C12 0.0273(6) 0.0297(7) 0.0262(6) 0.0020(5) -0.0062(5) -0.0010(5)
C13 0.0236(6) 0.0304(7) 0.0329(7) 0.0032(5) -0.0004(5) 0.0050(5)
C14 0.0282(6) 0.0278(6) 0.0271(6) -0.0003(5) 0.0037(5) 0.0051(5)
C15 0.0249(6) 0.0242(6) 0.0193(5) -0.0004(4) 0.0004(4) 0.0004(5)
C16 0.0246(6) 0.0332(7) 0.0342(7) 0.0001(6) 0.0088(5) -0.0073(5)
C17 0.0357(7) 0.0533(9) 0.0234(6) 0.0035(6) -0.0013(5) -0.0145(7)
#==============================================================================
# MOLECULAR GEOMETRY
_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
N1 C1 1.3190(15) . ?
N1 C2 1.3699(16) . ?
N2 C2 1.3373(15) . ?
N2 C6 1.3388(16) . ?
N3 C1 1.3322(16) . ?
N3 C16 1.4524(16) . ?
N3 C17 1.4570(17) . ?
O1 C7 1.2062(16) . ?
O2 C7 1.3298(15) . ?
O2 C8 1.4445(16) . ?
O3 C9 1.2350(15) . ?
O4 C11 1.3517(15) . ?
O4 H1 0.86(2) . ?
S1 C3 1.7310(12) . ?
S1 C1 1.7721(13) . ?
C2 C3 1.4243(16) . ?
C3 C4 1.3762(18) . ?
C4 C5 1.4005(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.4027(16) . ?
C5 C9 1.5010(17) . ?
C6 C7 1.5008(16) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.4704(17) . ?
C10 C15 1.4088(16) . ?
C10 C11 1.4099(17) . ?
C11 C12 1.3957(18) . ?
C12 C13 1.379(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3939(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.3776(17) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 109.43(10) . . ?
C2 N2 C6 116.68(10) . . ?
C1 N3 C16 122.00(11) . . ?
C1 N3 C17 119.56(11) . . ?
C16 N3 C17 118.41(11) . . ?
C7 O2 C8 115.34(11) . . ?
C11 O4 H1 104.3(15) . . ?
C3 S1 C1 88.15(6) . . ?
N1 C1 N3 124.08(11) . . ?
N1 C1 S1 116.60(9) . . ?
N3 C1 S1 119.31(9) . . ?
N2 C2 N1 121.66(10) . . ?
N2 C2 C3 122.19(11) . . ?
N1 C2 C3 116.15(10) . . ?
C4 C3 C2 120.58(11) . . ?
C4 C3 S1 129.67(9) . . ?
C2 C3 S1 109.65(9) . . ?
C3 C4 C5 117.19(11) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 H4 121.4 . . ?
C4 C5 C6 118.42(11) . . ?
C4 C5 C9 116.15(11) . . ?
C6 C5 C9 125.38(11) . . ?
N2 C6 C5 124.83(11) . . ?
N2 C6 C7 116.29(10) . . ?
C5 C6 C7 118.80(11) . . ?
O1 C7 O2 124.44(11) . . ?
O1 C7 C6 122.99(11) . . ?
O2 C7 C6 112.57(10) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 C10 121.06(11) . . ?
O3 C9 C5 117.67(11) . . ?
C10 C9 C5 120.95(10) . . ?
C15 C10 C11 117.87(11) . . ?
C15 C10 C9 122.65(11) . . ?
C11 C10 C9 119.47(11) . . ?
O4 C11 C12 117.36(11) . . ?
O4 C11 C10 122.16(11) . . ?
C12 C11 C10 120.48(11) . . ?
C13 C12 C11 119.99(12) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.65(12) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.57(12) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C10 121.41(12) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C2 N1 C1 N3 177.00(12) . . . . ?
C2 N1 C1 S1 -1.51(14) . . . . ?
C16 N3 C1 N1 176.05(13) . . . . ?
C17 N3 C1 N1 -2.0(2) . . . . ?
C16 N3 C1 S1 -5.48(18) . . . . ?
C17 N3 C1 S1 176.49(11) . . . . ?
C3 S1 C1 N1 1.39(11) . . . . ?
C3 S1 C1 N3 -177.20(11) . . . . ?
C6 N2 C2 N1 177.04(11) . . . . ?
C6 N2 C2 C3 -2.16(18) . . . . ?
C1 N1 C2 N2 -178.40(11) . . . . ?
C1 N1 C2 C3 0.86(15) . . . . ?
N2 C2 C3 C4 2.59(19) . . . . ?
N1 C2 C3 C4 -176.66(11) . . . . ?
N2 C2 C3 S1 179.39(9) . . . . ?
N1 C2 C3 S1 0.15(14) . . . . ?
C1 S1 C3 C4 175.65(13) . . . . ?
C1 S1 C3 C2 -0.78(9) . . . . ?
C2 C3 C4 C5 0.11(18) . . . . ?
S1 C3 C4 C5 -175.99(10) . . . . ?
C3 C4 C5 C6 -2.88(18) . . . . ?
C3 C4 C5 C9 174.63(11) . . . . ?
C2 N2 C6 C5 -0.87(18) . . . . ?
C2 N2 C6 C7 175.61(10) . . . . ?
C4 C5 C6 N2 3.48(19) . . . . ?
C9 C5 C6 N2 -173.78(12) . . . . ?
C4 C5 C6 C7 -172.92(11) . . . . ?
C9 C5 C6 C7 9.82(18) . . . . ?
C8 O2 C7 O1 1.98(19) . . . . ?
C8 O2 C7 C6 -178.16(11) . . . . ?
N2 C6 C7 O1 -148.68(12) . . . . ?
C5 C6 C7 O1 28.03(18) . . . . ?
N2 C6 C7 O2 31.47(15) . . . . ?
C5 C6 C7 O2 -151.83(11) . . . . ?
C4 C5 C9 O3 55.87(17) . . . . ?
C6 C5 C9 O3 -126.81(14) . . . . ?
C4 C5 C9 C10 -117.68(13) . . . . ?
C6 C5 C9 C10 59.64(18) . . . . ?
O3 C9 C10 C15 178.77(12) . . . . ?
C5 C9 C10 C15 -7.90(18) . . . . ?
O3 C9 C10 C11 -2.14(19) . . . . ?
C5 C9 C10 C11 171.19(11) . . . . ?
C15 C10 C11 O4 -179.76(12) . . . . ?
C9 C10 C11 O4 1.11(19) . . . . ?
C15 C10 C11 C12 -0.32(18) . . . . ?
C9 C10 C11 C12 -179.45(12) . . . . ?
O4 C11 C12 C13 178.61(12) . . . . ?
C10 C11 C12 C13 -0.9(2) . . . . ?
C11 C12 C13 C14 0.6(2) . . . . ?
C12 C13 C14 C15 0.9(2) . . . . ?
C13 C14 C15 C10 -2.1(2) . . . . ?
C11 C10 C15 C14 1.81(18) . . . . ?
C9 C10 C15 C14 -179.09(12) . . . . ?
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full 30.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max 0.358
_refine_diff_density_min -0.345
_refine_diff_density_rms 0.052
#===================== End of CIF submission =================================