# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2010
data_global
_journal_name_full Org.Biomol.Chem.
#TrackingRef '6a-new.cif'
_journal_coden_Cambridge 0177
_publ_contact_author_name 'Olivier Siri'
_publ_contact_author_address
;
CINaM, UPR 3118 CNRS, campus de Luminy, Marseille, France
;
_publ_contact_author_phone 0491829588
_publ_contact_author_fax 0491829580
_publ_contact_author_email siri@univmed.fr
_publ_contact_letter
;
;
_publ_requested_category FM
_publ_section_title
;
New Class of Highly stable Nonaromatic Tautomers
;
loop_
_publ_author_name
_publ_author_address
C.Seillan
;
CINaM, UPR 3118
Campus de Luminy
case 913
13288 Marseille cedex 09
France
;
P.Marsal
;
CINaM, UPR 3118
Campus de Luminy
case 913
13288 Marseille cedex 09
France
;
O.Siri
;
CINaM, UPR 3118
Campus de Luminy
case 913
13288 Marseille cedex 09
France
;
data_shelxl_6a
_database_code_depnum_ccdc_archive 'CCDC 701450'
#TrackingRef '6a-new.cif'
_audit_update_record
;
2010-03-30 # Formatted by publCIF
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C36 H40 N6 O2'
_chemical_formula_sum 'C36 H40 N6 O2'
_chemical_formula_weight 588.74
_chemical_compound_source 'synthesis as described'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Hexagonal
_symmetry_space_group_name_H-M 'R -3'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
_cell_length_a 26.389(2)
_cell_length_b 26.389(2)
_cell_length_c 23.753(1)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 120.00
_cell_volume 14325.0(16)
_cell_formula_units_Z 18
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 20962
_cell_measurement_theta_min 1.24
_cell_measurement_theta_max 26.76
_exptl_crystal_description needle
_exptl_crystal_colour red
_exptl_crystal_size_max .3
_exptl_crystal_size_mid .05
_exptl_crystal_size_min .05
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.228
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 5868
_exptl_absorpt_coefficient_mu 0.078
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 293(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 KappaCCD
_diffrn_measurement_method 'omega + phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number none
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 20962
_diffrn_reflns_av_R_equivalents 0.116
_diffrn_reflns_av_sigmaI/netI 0.0986
_diffrn_reflns_limit_h_min 0
_diffrn_reflns_limit_h_max 33
_diffrn_reflns_limit_k_min -28
_diffrn_reflns_limit_k_max 0
_diffrn_reflns_limit_l_min -29
_diffrn_reflns_limit_l_max 29
_diffrn_reflns_theta_min 1.24
_diffrn_reflns_theta_max 26.76
_diffrn_reflns_theta_full 26.76
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_reflns_number_total 6613
_reflns_number_gt 2791
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'KappaCCD (Bruker-Nonius, 1998)'
_computing_cell_refinement
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C.,
Polidori, G. and Camalli, M. J. Appl. Cryst. (1994). 27, 435-436
Bruker-Nonius (1998). Kappa CCD Reference Manual. Nonius B.V., P.O. Box
811, 2600 Av, Delft, The Netherlands.
Otwinowski, Z. and Minor, W. " Processing of X-ray Diffraction Data Collected
in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular
Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R.M. Sweet, Eds.,
Academic Press.
Sheldrick, G. M. (1997). SHELXL97. Program for the refinement of crystal
structures. Univ. of G\"ottingen, Germany.
;
_refine_special_details
;
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^ > 2sigma(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.
The bonds and ADP in the C19-C20(a-f) and C40-C41(a,b) moeties were
constrained using DFIX and ISOR shelx instruction. The bonds in
the C21---C44(a,b) moiety were constrained using DELU shelx instruction.
H13, H16, H34 and H37 were determined experimentally and refined
isotropically.
;
_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^)+(0.1284P)^2^+28.7216P] 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 6615
_refine_ls_number_parameters 469
_refine_ls_number_restraints 72
_refine_ls_R_factor_all 0.2421
_refine_ls_R_factor_gt 0.1161
_refine_ls_wR_factor_ref 0.3356
_refine_ls_wR_factor_gt 0.2621
_refine_ls_goodness_of_fit_ref 1.022
_refine_ls_restrained_S_all 1.026
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.308
_refine_diff_density_min -0.207
_refine_diff_density_rms 0.044
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 0.7108(2) -0.0610(2) 0.23559(19) 0.0763(12) Uani 1 1 d . E .
C2 C 0.6813(2) -0.0928(2) 0.1870(2) 0.0814(13) Uani 1 1 d . . .
C3 C 0.6235(2) -0.1473(2) 0.1930(2) 0.0856(14) Uani 1 1 d . . .
C4 C 0.6003(2) -0.1675(2) 0.2450(2) 0.0903(14) Uani 1 1 d . . .
H4 H 0.5656 -0.2030 0.2480 0.108 Uiso 1 1 calc R . .
C5 C 0.6279(2) -0.1357(2) 0.2942(2) 0.0813(13) Uani 1 1 d . . .
N6 N 0.60256(19) -0.15591(18) 0.3436(2) 0.0945(13) Uani 1 1 d . . .
C7 C 0.6291(3) -0.1225(3) 0.3899(2) 0.0930(15) Uani 1 1 d . . .
C8 C 0.6020(3) -0.1423(3) 0.4439(3) 0.1154(19) Uani 1 1 d . . .
H8 H 0.5676 -0.1780 0.4475 0.138 Uiso 1 1 calc R . .
C9 C 0.6276(4) -0.1075(3) 0.4904(3) 0.122(2) Uani 1 1 d . . .
H9 H 0.6097 -0.1201 0.5254 0.146 Uiso 1 1 calc R . .
C10 C 0.6788(3) -0.0547(3) 0.4866(2) 0.1120(19) Uani 1 1 d . . .
H10 H 0.6952 -0.0321 0.5187 0.134 Uiso 1 1 calc R . .
C11 C 0.7057(3) -0.0356(2) 0.4356(2) 0.1002(16) Uani 1 1 d . . .
H11 H 0.7405 -0.0001 0.4330 0.120 Uiso 1 1 calc R . .
C12 C 0.6808(3) -0.0693(2) 0.3874(2) 0.0875(14) Uani 1 1 d . . .
N13 N 0.7063(2) -0.0506(2) 0.33575(17) 0.0824(11) Uani 1 1 d . . .
C14 C 0.6830(2) -0.0812(2) 0.2879(2) 0.0765(12) Uani 1 1 d . . .
O15 O 0.70119(15) -0.07673(14) 0.13744(14) 0.0912(10) Uani 1 1 d . . .
N16 N 0.5987(2) -0.1726(2) 0.1435(2) 0.1112(17) Uani 1 1 d . . .
C17 C 0.5420(3) -0.2260(3) 0.1373(3) 0.146(3) Uani 1 1 d . . .
H17A H 0.5174 -0.2293 0.1691 0.176 Uiso 1 1 calc R . .
H17B H 0.5478 -0.2595 0.1381 0.176 Uiso 1 1 calc R . .
C18 C 0.5117(4) -0.2272(4) 0.0846(3) 0.209(5) Uani 1 1 d . A .
C19 C 0.4549(5) -0.2845(7) 0.0776(5) 0.294(9) Uani 1 1 d DU . .
C20A C 0.4287(6) -0.2826(7) 0.0227(6) 0.27(3) Uani 0.20 1 d PRDU A 1
C20B C 0.4052(6) -0.2733(7) 0.0721(5) 0.34(4) Uani 0.20 1 d PRDU A 2
C20C C 0.4130(6) -0.2941(7) 0.1239(6) 0.23(2) Uani 0.20 1 d PRDU A 3
C20D C 0.4444(5) -0.3240(7) 0.1263(6) 0.46(16) Uani 0.10 1 d PRDU A 4
C20E C 0.4680(5) -0.3332(8) 0.0770(5) 0.37(11) Uani 0.10 1 d PRDU A 5
C20F C 0.4601(5) -0.3125(7) 0.0252(5) 0.24(3) Uani 0.20 1 d PRDU A 6
C21 C 0.7702(2) -0.0063(2) 0.2330(2) 0.0823(13) Uani 1 1 d U . .
H21A H 0.7846 -0.0050 0.2713 0.099 Uiso 0.50 1 calc PR B 7
H21B H 0.7796 -0.0083 0.1934 0.099 Uiso 0.50 1 d PR B 8
C22 C 0.76826(18) 0.05010(19) 0.23124(18) 0.0719(11) Uani 1 1 d . E .
C23 C 0.77555(19) 0.0827(2) 0.2807(2) 0.0773(12) Uani 1 1 d . . .
C24 C 0.77425(19) 0.1380(2) 0.2778(2) 0.0777(12) Uani 1 1 d . E .
C25 C 0.7678(2) 0.1589(2) 0.22698(19) 0.0826(13) Uani 1 1 d . . .
H25 H 0.7690 0.1946 0.2254 0.099 Uiso 1 1 calc R E .
C26 C 0.75946(18) 0.1266(2) 0.17694(19) 0.0737(12) Uani 1 1 d . E .
N27 N 0.75233(17) 0.14818(17) 0.12914(16) 0.0830(11) Uani 1 1 d . . .
C28 C 0.7433(2) 0.1156(2) 0.08115(19) 0.0831(13) Uani 1 1 d . E .
C29 C 0.7356(2) 0.1370(3) 0.0289(2) 0.1060(17) Uani 1 1 d . . .
H29 H 0.7383 0.1734 0.0271 0.127 Uiso 1 1 calc R E .
C30 C 0.7243(3) 0.1044(3) -0.0186(2) 0.113(2) Uani 1 1 d . E .
H30 H 0.7193 0.1189 -0.0526 0.136 Uiso 1 1 calc R . .
C31 C 0.7202(2) 0.0502(3) -0.0172(2) 0.1085(18) Uani 1 1 d . . .
H31 H 0.7131 0.0289 -0.0503 0.130 Uiso 1 1 calc R E .
C32 C 0.7265(2) 0.0272(2) 0.0327(2) 0.0958(16) Uani 1 1 d . E .
H32 H 0.7228 -0.0097 0.0338 0.115 Uiso 1 1 calc R . .
C33 C 0.73880(19) 0.0609(2) 0.08196(19) 0.0800(13) Uani 1 1 d . . .
N34 N 0.74603(17) 0.0401(2) 0.13217(15) 0.0793(11) Uani 1 1 d . E .
C35 C 0.75795(19) 0.0709(2) 0.18088(18) 0.0736(12) Uani 1 1 d . . .
O36 O 0.78237(14) 0.06630(14) 0.32926(13) 0.0899(10) Uani 1 1 d . E .
N37 N 0.77907(19) 0.16383(18) 0.32827(18) 0.0893(12) Uani 1 1 d . . .
C38 C 0.7795(3) 0.2185(2) 0.3346(2) 0.1040(17) Uani 1 1 d . E .
H38A H 0.8167 0.2501 0.3214 0.125 Uiso 1 1 calc R . .
H38B H 0.7491 0.2176 0.3109 0.125 Uiso 1 1 calc R . .
C39 C 0.7705(4) 0.2307(3) 0.3912(3) 0.165(3) Uani 1 1 d D . .
H39A H 0.7983 0.2270 0.4150 0.198 Uiso 1 1 calc R E .
H39B H 0.7317 0.2006 0.4027 0.198 Uiso 1 1 calc R . .
C40 C 0.7758(6) 0.2881(4) 0.4027(4) 0.203(5) Uani 1 1 d D D .
H40A H 0.8149 0.3169 0.3905 0.244 Uiso 0.50 1 calc PR C 9
H40B H 0.7491 0.2912 0.3767 0.244 Uiso 0.50 1 calc PR C 9
H40C H 0.7811 0.2968 0.4427 0.244 Uiso 0.50 1 d PR C 10
H40D H 0.8109 0.3176 0.3840 0.244 Uiso 0.50 1 d PR C 10
C41A C 0.7678(11) 0.3085(8) 0.4535(6) 0.215(10) Uani 0.50 1 d PDU D 9
H41A H 0.7727 0.3468 0.4484 0.323 Uiso 0.50 1 calc PR D 9
H41B H 0.7960 0.3105 0.4802 0.323 Uiso 0.50 1 calc PR D 9
H41C H 0.7290 0.2824 0.4672 0.323 Uiso 0.50 1 calc PR D 9
C41B C 0.7267(11) 0.2918(13) 0.3874(11) 0.266(14) Uani 0.50 1 d PDU D 10
H41D H 0.7308 0.3279 0.4009 0.400 Uiso 0.50 1 calc PR D 10
H41E H 0.6923 0.2596 0.4035 0.400 Uiso 0.50 1 calc PR D 10
H41F H 0.7231 0.2903 0.3471 0.400 Uiso 0.50 1 calc PR D 10
C42A C 0.8164(4) -0.0076(4) 0.1994(4) 0.089(3) Uani 0.50 1 d PU E 7
H42A H 0.8154 0.0055 0.1615 0.106 Uiso 0.50 1 calc PR E 7
H42B H 0.8083 -0.0477 0.1970 0.106 Uiso 0.50 1 calc PR E 7
C42B C 0.8205(5) -0.0073(6) 0.2607(5) 0.120(4) Uani 0.50 1 d PU E 8
H42C H 0.8126 -0.0473 0.2635 0.144 Uiso 0.50 1 calc PR E 8
H42D H 0.8260 0.0087 0.2985 0.144 Uiso 0.50 1 calc PR E 8
C43 C 0.8782(3) 0.0310(4) 0.2241(4) 0.194(4) Uani 1 1 d U . .
H43A H 0.8781 0.0638 0.2423 0.232 Uiso 0.50 1 calc PR E 7
H43B H 0.9046 0.0469 0.1922 0.232 Uiso 0.50 1 calc PR E 7
H43C H 0.8623 0.0445 0.1947 0.232 Uiso 0.50 1 d PR E 8
H43D H 0.8992 0.0647 0.2484 0.232 Uiso 0.50 1 d PR E 8
C44A C 0.9091(19) 0.007(3) 0.2687(12) 0.59(5) Uani 0.50 1 d PU E 7
H44A H 0.9366 0.0384 0.2919 0.890 Uiso 0.50 1 calc PR E 7
H44B H 0.9292 -0.0093 0.2482 0.890 Uiso 0.50 1 calc PR E 7
H44C H 0.8796 -0.0232 0.2920 0.890 Uiso 0.50 1 calc PR E 7
C44B C 0.9246(9) 0.0321(10) 0.1988(16) 0.35(2) Uani 0.50 1 d PU E 8
H44D H 0.9453 0.0674 0.1771 0.532 Uiso 0.50 1 calc PR E 8
H44E H 0.9112 -0.0012 0.1744 0.532 Uiso 0.50 1 calc PR E 8
H44F H 0.9502 0.0310 0.2269 0.532 Uiso 0.50 1 calc PR E 8
H13 H 0.740(3) -0.010(3) 0.328(2) 0.15(2) Uiso 1 1 d . . .
H16 H 0.620(2) -0.159(2) 0.1160(19) 0.083(18) Uiso 1 1 d . . .
H34 H 0.728(2) -0.004(3) 0.136(2) 0.117(19) Uiso 1 1 d . . .
H37 H 0.785(2) 0.148(2) 0.362(2) 0.12(2) 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
C1 0.080(3) 0.076(3) 0.078(3) 0.006(2) 0.009(2) 0.043(3)
C2 0.094(4) 0.080(3) 0.078(3) -0.006(3) 0.003(3) 0.050(3)
C3 0.087(4) 0.071(3) 0.096(4) -0.014(3) 0.000(3) 0.038(3)
C4 0.088(4) 0.073(3) 0.101(4) -0.002(3) 0.010(3) 0.034(3)
C5 0.082(3) 0.075(3) 0.090(3) 0.007(3) 0.014(3) 0.041(3)
N6 0.102(3) 0.077(3) 0.103(3) 0.012(2) 0.019(3) 0.044(2)
C7 0.118(5) 0.088(4) 0.088(4) 0.014(3) 0.018(3) 0.063(4)
C8 0.153(6) 0.099(4) 0.103(4) 0.024(4) 0.028(4) 0.070(4)
C9 0.181(7) 0.123(6) 0.087(4) 0.024(4) 0.030(4) 0.095(6)
C10 0.159(6) 0.108(5) 0.081(4) 0.009(3) 0.004(4) 0.075(5)
C11 0.133(5) 0.098(4) 0.077(3) 0.006(3) 0.002(3) 0.063(4)
C12 0.107(4) 0.076(4) 0.091(4) 0.012(3) 0.007(3) 0.055(3)
N13 0.096(3) 0.075(3) 0.079(3) 0.007(2) 0.002(2) 0.044(3)
C14 0.086(3) 0.063(3) 0.085(3) -0.003(2) -0.003(3) 0.041(3)
O15 0.105(3) 0.088(2) 0.079(2) -0.0064(17) 0.0083(18) 0.047(2)
N16 0.105(4) 0.092(4) 0.108(4) -0.019(3) 0.005(3) 0.028(3)
C17 0.127(6) 0.114(5) 0.135(5) -0.035(4) 0.002(4) 0.014(5)
C18 0.143(7) 0.203(9) 0.138(6) -0.013(6) -0.038(5) -0.020(6)
C19 0.165(11) 0.39(2) 0.173(11) -0.010(12) -0.018(8) 0.025(13)
C20A 0.07(2) 0.50(8) 0.08(2) 0.00(3) 0.020(17) 0.02(3)
C20B 0.15(4) 0.54(10) 0.30(7) -0.11(6) 0.05(4) 0.14(6)
C20C 0.31(6) 0.20(5) 0.14(3) 0.01(3) -0.01(4) 0.10(4)
C20D 0.46(18) 0.42(18) 0.49(18) -0.08(10) 0.01(10) 0.20(11)
C20E 0.36(13) 0.37(14) 0.34(13) 0.00(9) 0.17(9) 0.14(9)
C20F 0.29(7) 0.16(4) 0.23(5) -0.05(4) -0.01(5) 0.08(4)
C21 0.079(3) 0.080(3) 0.094(3) 0.004(2) 0.002(2) 0.044(3)
C22 0.068(3) 0.070(3) 0.075(3) -0.002(2) -0.001(2) 0.033(2)
C23 0.070(3) 0.075(3) 0.082(3) 0.008(2) -0.001(2) 0.032(3)
C24 0.072(3) 0.069(3) 0.083(3) -0.003(2) -0.002(2) 0.028(2)
C25 0.085(3) 0.071(3) 0.089(3) 0.000(3) -0.004(2) 0.037(3)
C26 0.066(3) 0.064(3) 0.082(3) 0.000(2) 0.002(2) 0.026(2)
N27 0.087(3) 0.079(3) 0.075(3) 0.008(2) 0.0003(19) 0.035(2)
C28 0.078(3) 0.081(4) 0.076(3) 0.006(3) 0.002(2) 0.029(3)
C29 0.123(5) 0.099(4) 0.084(4) 0.014(3) -0.004(3) 0.046(4)
C30 0.123(5) 0.117(5) 0.072(4) 0.009(3) -0.007(3) 0.039(4)
C31 0.099(4) 0.116(5) 0.077(4) 0.000(3) 0.005(3) 0.028(4)
C32 0.092(4) 0.091(4) 0.080(3) -0.006(3) 0.008(3) 0.029(3)
C33 0.074(3) 0.081(3) 0.074(3) 0.004(3) 0.002(2) 0.030(3)
N34 0.078(3) 0.072(3) 0.074(3) 0.002(2) 0.0059(19) 0.027(2)
C35 0.067(3) 0.073(3) 0.072(3) 0.001(2) 0.002(2) 0.029(2)
O36 0.100(2) 0.085(2) 0.078(2) 0.0015(16) -0.0101(17) 0.042(2)
N37 0.111(3) 0.079(3) 0.077(3) -0.008(2) -0.008(2) 0.047(3)
C38 0.122(5) 0.082(4) 0.099(4) -0.018(3) -0.003(3) 0.045(3)
C39 0.293(11) 0.119(6) 0.114(5) -0.020(4) -0.022(5) 0.125(7)
C40 0.327(16) 0.143(8) 0.159(8) -0.033(6) -0.009(9) 0.132(9)
C41A 0.38(3) 0.166(15) 0.137(13) -0.044(11) -0.002(15) 0.162(18)
C41B 0.31(3) 0.31(3) 0.26(3) -0.11(2) -0.09(2) 0.22(3)
C42A 0.090(6) 0.082(7) 0.105(7) 0.013(5) 0.019(5) 0.051(5)
C42B 0.113(8) 0.120(10) 0.122(9) 0.017(7) -0.025(6) 0.054(8)
C43 0.080(4) 0.202(9) 0.281(11) -0.015(7) 0.002(5) 0.057(5)
C44A 0.51(6) 1.33(15) 0.28(4) 0.00(6) -0.10(4) 0.71(9)
C44B 0.106(15) 0.20(2) 0.71(6) -0.13(3) 0.11(2) 0.035(14)
_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 C14 1.404(6) . ?
C1 C2 1.409(6) . ?
C1 C21 1.511(6) . ?
C2 O15 1.273(5) . ?
C2 C3 1.491(7) . ?
C3 N16 1.350(7) . ?
C3 C4 1.361(6) . ?
C4 C5 1.410(7) . ?
C4 H4 0.9300 . ?
C5 N6 1.325(6) . ?
C5 C14 1.455(7) . ?
N6 C7 1.363(6) . ?
C7 C12 1.385(7) . ?
C7 C8 1.435(7) . ?
C8 C9 1.378(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.396(7) . ?
C11 H11 0.9300 . ?
C12 N13 1.367(6) . ?
N13 C14 1.351(6) . ?
N13 H13 1.02(7) . ?
N16 C17 1.461(7) . ?
N16 H16 0.82(4) . ?
C17 C18 1.477(10) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.514(13) . ?
C19 C20F 1.489(8) . ?
C19 C20D 1.489(8) . ?
C19 C20A 1.489(8) . ?
C19 C20E 1.489(8) . ?
C19 C20C 1.489(8) . ?
C19 C20B 1.489(8) . ?
C21 C42A 1.471(10) . ?
C21 C42B 1.494(12) . ?
C21 C22 1.515(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9801 . ?
C22 C35 1.399(6) . ?
C22 C23 1.412(6) . ?
C23 O36 1.275(5) . ?
C23 C24 1.479(6) . ?
C24 N37 1.354(6) . ?
C24 C25 1.371(6) . ?
C25 C26 1.413(6) . ?
C25 H25 0.9300 . ?
C26 N27 1.325(5) . ?
C26 C35 1.453(6) . ?
N27 C28 1.376(6) . ?
C28 C33 1.387(7) . ?
C28 C29 1.420(7) . ?
C29 C30 1.357(7) . ?
C29 H29 0.9300 . ?
C30 C31 1.379(8) . ?
C30 H30 0.9300 . ?
C31 C32 1.379(7) . ?
C31 H31 0.9300 . ?
C32 C33 1.405(6) . ?
C32 H32 0.9300 . ?
C33 N34 1.365(6) . ?
N34 C35 1.357(5) . ?
N34 H34 1.02(6) . ?
N37 C38 1.445(6) . ?
N37 H37 0.95(5) . ?
C38 C39 1.430(7) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.477(9) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41A 1.379(12) . ?
C40 C41B 1.395(15) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C40 H40C 0.9700 . ?
C40 H40D 0.9700 . ?
C41A H40C 0.6272 . ?
C41A H41A 0.9600 . ?
C41A H41B 0.9600 . ?
C41A H41C 0.9600 . ?
C41B H41D 0.9600 . ?
C41B H41E 0.9600 . ?
C41B H41F 0.9600 . ?
C42A C43 1.543(12) . ?
C42A H21B 0.9723 . ?
C42A H42A 0.9700 . ?
C42A H42B 0.9700 . ?
C42A H43C 1.3058 . ?
C42B C43 1.600(14) . ?
C42B H42C 0.9700 . ?
C42B H42D 0.9700 . ?
C43 C44B 1.349(19) . ?
C43 C44A 1.65(3) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C43 H43C 0.9700 . ?
C43 H43D 0.9700 . ?
C44A H44A 0.9600 . ?
C44A H44B 0.9600 . ?
C44A H44C 0.9600 . ?
C44B H44D 0.9600 . ?
C44B H44E 0.9600 . ?
C44B H44F 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 C1 C2 118.1(5) . . ?
C14 C1 C21 119.6(4) . . ?
C2 C1 C21 122.3(4) . . ?
O15 C2 C1 123.1(5) . . ?
O15 C2 C3 117.5(4) . . ?
C1 C2 C3 119.3(4) . . ?
N16 C3 C4 125.8(5) . . ?
N16 C3 C2 113.7(5) . . ?
C4 C3 C2 120.5(5) . . ?
C3 C4 C5 121.4(5) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
N6 C5 C4 119.3(5) . . ?
N6 C5 C14 122.9(5) . . ?
C4 C5 C14 117.8(4) . . ?
C5 N6 C7 117.5(5) . . ?
N6 C7 C12 123.3(5) . . ?
N6 C7 C8 118.9(6) . . ?
C12 C7 C8 117.8(6) . . ?
C9 C8 C7 119.0(6) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C10 C9 C8 121.9(6) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C11 C10 C9 119.8(6) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.0(6) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
N13 C12 C7 117.4(5) . . ?
N13 C12 C11 121.1(5) . . ?
C7 C12 C11 121.5(5) . . ?
C14 N13 C12 123.0(5) . . ?
C14 N13 H13 113(3) . . ?
C12 N13 H13 124(3) . . ?
N13 C14 C1 121.5(5) . . ?
N13 C14 C5 115.8(4) . . ?
C1 C14 C5 122.7(4) . . ?
C3 N16 C17 125.0(6) . . ?
C3 N16 H16 115(4) . . ?
C17 N16 H16 120(4) . . ?
N16 C17 C18 112.8(6) . . ?
N16 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
N16 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 C19 111.8(8) . . ?
C20F C19 C18 107.3(7) . . ?
C20D C19 C18 111.0(6) . . ?
C20A C19 C18 107.9(6) . . ?
C20E C19 C18 108.8(9) . . ?
C20C C19 C18 111.7(7) . . ?
C20B C19 C18 110.1(9) . . ?
C42A C21 C1 118.4(5) . . ?
C42B C21 C1 118.1(6) . . ?
C42A C21 C22 116.4(5) . . ?
C42B C21 C22 119.7(6) . . ?
C1 C21 C22 114.3(4) . . ?
C42A C21 H21A 101.2 . . ?
C1 C21 H21A 101.2 . . ?
C22 C21 H21A 101.2 . . ?
C42B C21 H21B 99.9 . . ?
C1 C21 H21B 99.0 . . ?
C22 C21 H21B 99.3 . . ?
C35 C22 C23 117.8(4) . . ?
C35 C22 C21 121.2(4) . . ?
C23 C22 C21 121.0(4) . . ?
O36 C23 C22 123.1(4) . . ?
O36 C23 C24 117.1(4) . . ?
C22 C23 C24 119.9(4) . . ?
N37 C24 C25 125.3(5) . . ?
N37 C24 C23 114.3(4) . . ?
C25 C24 C23 120.4(4) . . ?
C24 C25 C26 120.8(5) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
N27 C26 C25 118.4(4) . . ?
N27 C26 C35 123.5(4) . . ?
C25 C26 C35 118.1(4) . . ?
C26 N27 C28 117.3(4) . . ?
N27 C28 C33 122.5(4) . . ?
N27 C28 C29 119.3(5) . . ?
C33 C28 C29 118.1(5) . . ?
C30 C29 C28 120.3(6) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C31 121.0(5) . . ?
C29 C30 H30 119.5 . . ?
C31 C30 H30 119.5 . . ?
C32 C31 C30 120.8(6) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C31 C32 C33 118.6(6) . . ?
C31 C32 H32 120.7 . . ?
C33 C32 H32 120.7 . . ?
N34 C33 C28 118.2(4) . . ?
N34 C33 C32 120.5(5) . . ?
C28 C33 C32 121.3(5) . . ?
C35 N34 C33 122.8(5) . . ?
C35 N34 H34 116(3) . . ?
C33 N34 H34 118(3) . . ?
N34 C35 C22 121.7(4) . . ?
N34 C35 C26 115.6(4) . . ?
C22 C35 C26 122.7(4) . . ?
C24 N37 C38 123.1(4) . . ?
C24 N37 H37 121(3) . . ?
C38 N37 H37 116(3) . . ?
C39 C38 N37 113.7(5) . . ?
C39 C38 H38A 108.8 . . ?
N37 C38 H38A 108.8 . . ?
C39 C38 H38B 108.8 . . ?
N37 C38 H38B 108.8 . . ?
H38A C38 H38B 107.7 . . ?
C38 C39 C40 117.6(6) . . ?
C38 C39 H39A 107.9 . . ?
C40 C39 H39A 107.9 . . ?
C38 C39 H39B 107.9 . . ?
C40 C39 H39B 107.9 . . ?
H39A C39 H39B 107.2 . . ?
C41A C40 C39 127.4(11) . . ?
C41B C40 C39 114.1(16) . . ?
C41A C40 H40A 105.4 . . ?
C41B C40 H40A 121.9 . . ?
C39 C40 H40A 105.4 . . ?
C41A C40 H40B 105.4 . . ?
C39 C40 H40B 105.4 . . ?
H40A C40 H40B 106.0 . . ?
C41B C40 H40C 105.6 . . ?
C39 C40 H40C 110.6 . . ?
H40A C40 H40C 97.8 . . ?
H40B C40 H40C 129.0 . . ?
C41A C40 H40D 111.1 . . ?
C41B C40 H40D 111.9 . . ?
C39 C40 H40D 107.5 . . ?
H40B C40 H40D 94.8 . . ?
H40C C40 H40D 107.0 . . ?
C40 C41A H41A 109.5 . . ?
C40 C41A H41B 109.5 . . ?
H41A C41A H41B 109.5 . . ?
C40 C41A H41C 109.5 . . ?
H40C C41A H41C 116.3 . . ?
H41A C41A H41C 109.5 . . ?
H41B C41A H41C 109.5 . . ?
C40 C41B H41D 109.5 . . ?
C40 C41B H41E 109.5 . . ?
H41D C41B H41E 109.5 . . ?
C40 C41B H41F 109.5 . . ?
H41D C41B H41F 109.5 . . ?
H41E C41B H41F 109.5 . . ?
C21 C42A C43 113.2(8) . . ?
C21 C42A H42A 108.9 . . ?
C43 C42A H42A 108.9 . . ?
C21 C42A H42B 108.9 . . ?
C43 C42A H42B 108.9 . . ?
H21B C42A H42B 107.3 . . ?
H42A C42A H42B 107.7 . . ?
C21 C42A H43C 111.5 . . ?
H21B C42A H43C 113.6 . . ?
C21 C42B C43 108.8(8) . . ?
C21 C42B H42C 109.9 . . ?
C43 C42B H42C 109.9 . . ?
C21 C42B H42D 109.9 . . ?
C43 C42B H42D 109.9 . . ?
H42C C42B H42D 108.3 . . ?
C44B C43 C42A 119.6(16) . . ?
C42A C43 C44A 124(2) . . ?
C44B C43 H43A 125.9 . . ?
C42A C43 H43A 106.4 . . ?
C44A C43 H43A 106.4 . . ?
C42A C43 H43B 106.4 . . ?
C44A C43 H43B 106.4 . . ?
H43A C43 H43B 106.5 . . ?
C44B C43 H43C 103.0 . . ?
C42B C43 H43C 100.0 . . ?
C42B C43 H43D 100.5 . . ?
H43B C43 H43D 96.3 . . ?
H43C C43 H43D 104.2 . . ?
C43 C44A H44A 109.5 . . ?
C43 C44A H44B 109.5 . . ?
H44A C44A H44B 109.5 . . ?
C43 C44A H44C 109.5 . . ?
H44A C44A H44C 109.5 . . ?
H44B C44A H44C 109.5 . . ?
C43 C44B H44D 109.5 . . ?
C43 C44B H44E 109.5 . . ?
H44D C44B H44E 109.5 . . ?
C43 C44B H44F 109.5 . . ?
H44D C44B H44F 109.5 . . ?
H44E C44B H44F 109.5 . . ?
# Attachment '8-new.cif'
#data_8a
#TrackingRef '8-new.cif'
data_shelxl_8a
_database_code_depnum_ccdc_archive 'CCDC 701451'
#TrackingRef '8-new.cif'
_audit_update_record
;
2008-05-28 # Formatted by publCIF
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C12 H8 N2 O'
_chemical_formula_sum 'C12 H8 N2 O'
_chemical_formula_weight 196.20
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 'C 2/c'
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 18.931(1)
_cell_length_b 4.4136(3)
_cell_length_c 22.572(2)
_cell_angle_alpha 90.00
_cell_angle_beta 96.459(2)
_cell_angle_gamma 90.00
_cell_volume 1874.0(2)
_cell_formula_units_Z 8
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 4305
_cell_measurement_theta_min 0.91
_cell_measurement_theta_max 22.31
_exptl_crystal_description prism
_exptl_crystal_colour 'pale red'
_exptl_crystal_size_max .3
_exptl_crystal_size_mid .15
_exptl_crystal_size_min .025
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.391
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 816
_exptl_absorpt_coefficient_mu 0.092
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 293(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 KappaCCD
_diffrn_measurement_method 'Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number none
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 4305
_diffrn_reflns_av_R_equivalents 0.086
_diffrn_reflns_av_sigmaI/netI 0.0475
_diffrn_reflns_limit_h_min 0
_diffrn_reflns_limit_h_max 20
_diffrn_reflns_limit_k_min 0
_diffrn_reflns_limit_k_max 4
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_theta_min 4.02
_diffrn_reflns_theta_max 22.31
_reflns_number_total 1177
_reflns_number_gt 803
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'KappaCCD (Bruker-Nonius, 1998)'
_computing_cell_refinement
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C.,
Polidori, G. and Camalli, M. J. Appl. Cryst. (1994). 27, 435-436
Bruker-Nonius (1998). Kappa CCD Reference Manual. Nonius B.V., P.O. Box
811, 2600 Av, Delft, The Netherlands.
Otwinowski, Z. and Minor, W. " Processing of X-ray Diffraction Data Collected
in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular
Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R.M. Sweet, Eds.,
Academic Press.
Sheldrick, G. M. (1997). SHELXL97. Program for the refinement of crystal
structures. Univ. of G\"ottingen, Germany.
;
_refine_special_details
;
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^ > 2sigma(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.
H15 was determined experimentally and refined isotropically
;
_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^)+(0.0405P)^2^+1.6222P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_number_reflns 1177
_refine_ls_number_parameters 140
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0781
_refine_ls_R_factor_gt 0.0487
_refine_ls_wR_factor_ref 0.1244
_refine_ls_wR_factor_gt 0.1084
_refine_ls_goodness_of_fit_ref 1.083
_refine_ls_restrained_S_all 1.083
_refine_ls_shift/su_max 0
_refine_ls_shift/su_mean 0
_refine_diff_density_max 0.115
_refine_diff_density_min -0.12
_refine_diff_density_rms 0.029
_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full 22.31
_diffrn_measured_fraction_theta_full 0.978
#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL 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
C1 C 0.25493(13) 1.2011(6) 0.18944(11) 0.0502(7) Uani 1 1 d . . .
H1 H 0.2468 1.2636 0.2274 0.06 Uiso 1 1 calc R . .
C2 C 0.31361(15) 1.2983(6) 0.16592(12) 0.0540(7) Uani 1 1 d . . .
C3 C 0.32436(15) 1.2195(7) 0.10636(12) 0.0607(8) Uani 1 1 d . . .
H3 H 0.3637 1.2949 0.09 0.073 Uiso 1 1 calc R . .
C4 C 0.27812(15) 1.0368(7) 0.07345(12) 0.0607(8) Uani 1 1 d . . .
H4 H 0.286 0.9873 0.0347 0.073 Uiso 1 1 calc R . .
C5 C 0.21738(14) 0.9191(6) 0.09744(11) 0.0499(7) Uani 1 1 d . . .
N6 N 0.17329(12) 0.7306(5) 0.06523(9) 0.0578(7) Uani 1 1 d . . .
C7 C 0.11751(14) 0.6216(6) 0.09130(12) 0.0543(7) Uani 1 1 d . . .
C8 C 0.06935(16) 0.4168(7) 0.05992(13) 0.0687(9) Uani 1 1 d . . .
H8 H 0.0765 0.3575 0.0215 0.082 Uiso 1 1 calc R . .
C9 C 0.01333(17) 0.3064(8) 0.08491(16) 0.0789(10) Uani 1 1 d . . .
H9 H -0.0178 0.1724 0.0636 0.095 Uiso 1 1 calc R . .
C10 C 0.00162(16) 0.3932(8) 0.14335(15) 0.0755(10) Uani 1 1 d . . .
H10 H -0.0375 0.3176 0.1601 0.091 Uiso 1 1 calc R . .
C11 C 0.04689(15) 0.5853(7) 0.17494(13) 0.0660(9) Uani 1 1 d . . .
H11 H 0.0391 0.6376 0.2136 0.079 Uiso 1 1 calc R . .
C12 C 0.10585(13) 0.7079(6) 0.15019(12) 0.0513(7) Uani 1 1 d . . .
N13 N 0.15016(11) 0.9011(5) 0.18249(9) 0.0510(6) Uani 1 1 d . . .
C14 C 0.20605(13) 1.0063(6) 0.15696(11) 0.0476(7) Uani 1 1 d . . .
O15 O 0.36437(10) 1.4730(5) 0.19654(10) 0.0704(7) Uani 1 1 d . . .
H15 H 0.359(2) 1.446(12) 0.241(2) 0.19(2) 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
C1 0.0584(17) 0.0567(18) 0.0377(15) 0.0001(13) 0.0153(13) 0.0027(14)
C2 0.0583(18) 0.0562(18) 0.0492(17) 0.0018(14) 0.0128(14) -0.0021(15)
C3 0.0653(19) 0.072(2) 0.0498(17) 0.0015(16) 0.0267(15) -0.0022(16)
C4 0.072(2) 0.071(2) 0.0427(16) -0.0003(15) 0.0236(15) 0.0018(17)
C5 0.0556(17) 0.0567(18) 0.0387(15) 0.0017(14) 0.0111(13) 0.0077(15)
N6 0.0653(16) 0.0644(15) 0.0442(14) 0.0008(12) 0.0089(12) 0.0048(13)
C7 0.0570(18) 0.0566(18) 0.0495(17) 0.0026(15) 0.0073(14) 0.0075(15)
C8 0.075(2) 0.071(2) 0.0573(19) -0.0024(17) -0.0030(17) -0.0022(18)
C9 0.070(2) 0.077(2) 0.087(3) 0.003(2) -0.0033(19) -0.0137(18)
C10 0.0599(19) 0.082(2) 0.085(2) 0.012(2) 0.0125(18) -0.0045(18)
C11 0.060(2) 0.075(2) 0.065(2) 0.0016(17) 0.0176(16) -0.0007(17)
C12 0.0468(16) 0.0545(18) 0.0538(17) 0.0055(15) 0.0104(14) 0.0066(14)
N13 0.0520(14) 0.0592(15) 0.0438(13) 0.0025(12) 0.0138(11) 0.0052(12)
C14 0.0530(16) 0.0510(16) 0.0410(15) 0.0036(13) 0.0145(13) 0.0078(14)
O15 0.0706(13) 0.0856(15) 0.0580(13) -0.0003(12) 0.0198(11) -0.0172(12)
#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#
_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 C2 1.354(3) . ?
C1 C14 1.407(3) . ?
C1 H1 0.93 . ?
C2 O15 1.358(3) . ?
C2 C3 1.425(4) . ?
C3 C4 1.350(4) . ?
C3 H3 0.93 . ?
C4 C5 1.423(4) . ?
C4 H4 0.93 . ?
C5 N6 1.335(3) . ?
C5 C14 1.437(3) . ?
N6 C7 1.354(3) . ?
C7 C8 1.416(4) . ?
C7 C12 1.424(4) . ?
C8 C9 1.347(4) . ?
C8 H8 0.93 . ?
C9 C10 1.415(4) . ?
C9 H9 0.93 . ?
C10 C11 1.351(4) . ?
C10 H10 0.93 . ?
C11 C12 1.411(4) . ?
C11 H11 0.93 . ?
C12 N13 1.351(3) . ?
N13 C14 1.343(3) . ?
O15 H15 1.04(5) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C14 120.7(2) . . ?
C2 C1 H1 119.7 . . ?
C14 C1 H1 119.7 . . ?
C1 C2 O15 123.0(2) . . ?
C1 C2 C3 120.2(3) . . ?
O15 C2 C3 116.8(2) . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
N6 C5 C4 120.2(2) . . ?
N6 C5 C14 121.8(2) . . ?
C4 C5 C14 118.0(3) . . ?
C5 N6 C7 117.1(2) . . ?
N6 C7 C8 120.0(3) . . ?
N6 C7 C12 121.4(3) . . ?
C8 C7 C12 118.6(3) . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 121.0(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
N13 C12 C11 119.9(3) . . ?
N13 C12 C7 121.4(2) . . ?
C11 C12 C7 118.7(3) . . ?
C14 N13 C12 117.2(2) . . ?
N13 C14 C1 119.4(2) . . ?
N13 C14 C5 121.1(2) . . ?
C1 C14 C5 119.5(2) . . ?
C2 O15 H15 107(3) . . ?
# END of CIF