# Electronic Supplementary Material (ESI) for Medical Chemistry Communications
# This journal is © The Royal Society of Chemistry 2011
data_global
_journal_name_full MedChemComm
_journal_coden_cambridge 1476
#TrackingRef '4mepr acta.cif'
#------------------ AUDIT DETAILS -------------------------------------------#
_audit_creation_date 2010-11-15
_audit_creation_method 'WinGX routine CIF_UPDATE'
_audit_conform_dict_name cif_core.dic
_audit_conform_dict_version 2.3
_audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic
#=========================================================================
# PROCESSING SUMMARY (IUCr Office Use Only)
_journal_date_recd_electronic ?
_journal_date_to_coeditor ?
_journal_date_from_coeditor ?
_journal_date_accepted ?
_journal_date_printers_first ?
_journal_date_printers_final ?
_journal_date_proofs_out ?
_journal_date_proofs_in ?
_journal_coeditor_name ?
_journal_coeditor_code ?
_journal_coeditor_notes
; ?
;
_journal_paper_category ?
_journal_techeditor_code ?
_journal_techeditor_notes
; ?
;
_journal_coden_ASTM ?
_journal_year ?
_journal_volume ?
_journal_issue ?
_journal_page_first ?
_journal_page_last ?
_journal_suppl_publ_number ?
_journal_suppl_publ_pages ?
#=========================================================================
# SUBMISSION DETAILS
_publ_contact_author_name 'J Kalyana Sundar'
_publ_contact_author_address
;
?
;
_publ_contact_author_email jksundar50@gmail.com
_publ_contact_author_fax ?
_publ_contact_author_phone ?
_publ_contact_letter
;
Please consider this CIF submission for publication
in Medicinal Chemistry Communication.
;
_publ_requested_category ?
_publ_requested_coeditor_name ?
#=========================================================================
# TITLE AND AUTHOR LIST
_publ_section_title
;
?
;
_publ_section_title_footnote .
loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
'S. Michael Rajesh'
;
Department of Organic Chemistry
Madurai Kamaraj University
Madurai - 625 021
INDIA.
;
.
J.Sivamani
;
Department of Organic Chemistry
Madurai Kamaraj University
Madurai - 625 021
INDIA.
;
.
J.K.sundar '' ''
'S. Perumal' '' ''
S.Natarajan '' ''
#=========================================================================
# TEXT
_publ_section_abstract
;
?
;
_publ_section_comment
;
?
;
_publ_section_acknowledgements
;
The author thanks the DST for the FIST
programme.
;
_publ_section_references
;
Enraf-Nonius (1994). CAD-4 Software version 5.0, Enraf-Nonius, Delft,
The Netherlands.
Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24,
351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7--13.
;
_publ_section_figure_captions
;
Figure 1 The molecular structure of (I), showing 30% probability displacement
ellipsoids and the atom-numbering scheme.
;
_publ_section_exptl_prep
;
?
;
_publ_section_exptl_refinement
;
H atoms were placed at calculated positions and allowed to
ride on their carrier atoms with C---H = 0.93--0.97\%A, and U~iso~ =
1.2U~eq~(C) for CH~2~ and CH groups and U~iso~ =
1.5U~eq~(C) for CH~3~ group.
;
data_4mepr
_database_code_depnum_ccdc_archive 'CCDC 800956'
#TrackingRef '4mepr acta.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C22 H23 N3 O5'
_chemical_formula_sum 'C22 H23 N3 O5'
_chemical_formula_weight 409.43
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/a'
_symmetry_space_group_name_Hall '-P 2yab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
_cell_length_a 9.676(5)
_cell_length_b 14.400(5)
_cell_length_c 14.309(5)
_cell_angle_alpha 90.000(5)
_cell_angle_beta 91.333(5)
_cell_angle_gamma 90.000(5)
_cell_volume 1993.2(14)
_cell_formula_units_Z 4
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 25
_cell_measurement_theta_min 2
_cell_measurement_theta_max 25
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.18
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.13
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.364
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 864
_exptl_absorpt_coefficient_mu 0.098
_exptl_absorpt_correction_type psi-scan
_exptl_absorpt_correction_T_min 0.9490
_exptl_absorpt_correction_T_max 0.9630
_exptl_absorpt_process_details '(North et al., 1968)'
_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 MACH3-Nonius
_diffrn_measurement_method \w-2\q
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time 60
_diffrn_standards_decay_% 0
_diffrn_reflns_number 8147
_diffrn_reflns_av_R_equivalents 0.0390
_diffrn_reflns_av_sigmaI/netI 0.0424
_diffrn_reflns_limit_h_min -1
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_theta_min 2.01
_diffrn_reflns_theta_max 24.97
_reflns_number_total 3500
_reflns_number_gt 2384
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CAD4 Express (Enraf Nonius, (1994)'
_computing_cell_refinement 'CAD4 Express (Enraf Nonius, (1994)'
_computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1996)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'PLATON (Spek, 2009)'
_computing_publication_material SHELXL-97
_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.
;
_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^)+(0.0618P)^2^+0.2249P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3500
_refine_ls_number_parameters 275
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0820
_refine_ls_R_factor_gt 0.0492
_refine_ls_wR_factor_ref 0.1421
_refine_ls_wR_factor_gt 0.1258
_refine_ls_goodness_of_fit_ref 1.018
_refine_ls_restrained_S_all 1.018
_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
O1 O 0.20067(17) 0.40556(12) 0.90587(11) 0.0479(5) Uani 1 1 d . . .
O2 O 0.41309(18) 0.57424(12) 0.58361(10) 0.0468(5) Uani 1 1 d . . .
C3 C 0.3372(2) 0.42465(14) 0.89132(14) 0.0347(5) Uani 1 1 d . . .
N1A N 0.3878(2) 0.41689(14) 0.56370(14) 0.0416(5) Uani 1 1 d . . .
C5 C 0.2455(2) 0.52696(13) 0.76168(13) 0.0282(5) Uani 1 1 d . . .
H5 H 0.1611 0.5109 0.7946 0.034 Uiso 1 1 calc R . .
C2A C 0.3647(2) 0.48847(14) 0.81980(13) 0.0306(5) Uani 1 1 d . . .
C1A C 0.2392(2) 0.63022(14) 0.74358(14) 0.0343(5) Uani 1 1 d . . .
H1A H 0.3314 0.6518 0.7267 0.041 Uiso 1 1 calc R . .
O1A O 0.2035(3) 0.76919(14) 0.81938(16) 0.0929(9) Uani 1 1 d . . .
C9 C 0.5803(3) 0.41128(17) 0.92692(16) 0.0449(6) Uani 1 1 d . . .
H9 H 0.6520 0.3854 0.9627 0.054 Uiso 1 1 calc R . .
N4A N 0.12081(19) 0.54784(13) 0.61667(11) 0.0362(5) Uani 1 1 d . . .
C12 C 0.5007(2) 0.51213(15) 0.80440(15) 0.0357(5) Uani 1 1 d . . .
H12 H 0.5205 0.5547 0.7576 0.043 Uiso 1 1 calc R . .
C13 C 0.2057(2) 0.38362(15) 0.65597(14) 0.0333(5) Uani 1 1 d . . .
O2A O 0.1388(2) 0.64750(14) 0.89024(13) 0.0735(7) Uani 1 1 d . . .
C15 C 0.1393(3) 0.64259(16) 0.65761(15) 0.0411(6) Uani 1 1 d . . .
H15 H 0.1834 0.6827 0.6117 0.049 Uiso 1 1 calc R . .
N2A N 0.1918(2) 0.68546(14) 0.82541(14) 0.0477(6) Uani 1 1 d . . .
C17 C 0.2279(2) 0.48747(14) 0.66130(13) 0.0302(5) Uani 1 1 d . . .
C18 C 0.4449(3) 0.38678(16) 0.94402(16) 0.0437(6) Uani 1 1 d . . .
H18 H 0.4261 0.3446 0.9912 0.052 Uiso 1 1 calc R . .
C19 C 0.1168(3) 0.32524(17) 0.70265(17) 0.0446(6) Uani 1 1 d . . .
H19 H 0.0520 0.3495 0.7430 0.054 Uiso 1 1 calc R . .
C20 C -0.0244(3) 0.52106(18) 0.62714(17) 0.0486(6) Uani 1 1 d . . .
H20A H -0.0395 0.4937 0.6880 0.058 Uiso 1 1 calc R . .
H20B H -0.0539 0.4775 0.5789 0.058 Uiso 1 1 calc R . .
C21 C 0.1255(3) 0.22971(18) 0.6884(2) 0.0566(7) Uani 1 1 d . . .
H21 H 0.0669 0.1898 0.7199 0.068 Uiso 1 1 calc R . .
C22 C 0.3029(2) 0.34576(16) 0.59765(14) 0.0381(5) Uani 1 1 d . . .
C23 C 0.3569(2) 0.50000(16) 0.59963(14) 0.0347(5) Uani 1 1 d . . .
C24 C 0.6094(2) 0.47349(16) 0.85762(16) 0.0395(6) Uani 1 1 d . . .
C25 C 0.3120(3) 0.25131(18) 0.58178(18) 0.0521(7) Uani 1 1 d . . .
H25 H 0.3771 0.2272 0.5416 0.063 Uiso 1 1 calc R . .
C26 C -0.0989(3) 0.6127(2) 0.6167(2) 0.0653(8) Uani 1 1 d . . .
H26A H -0.1911 0.6096 0.6417 0.078 Uiso 1 1 calc R . .
H26B H -0.1052 0.6319 0.5517 0.078 Uiso 1 1 calc R . .
C27 C -0.0069(3) 0.6778(2) 0.6737(2) 0.0662(9) Uani 1 1 d . . .
H27A H -0.0288 0.6748 0.7394 0.079 Uiso 1 1 calc R . .
H27B H -0.0174 0.7413 0.6522 0.079 Uiso 1 1 calc R . .
C28 C 0.1695(4) 0.3315(2) 0.9669(3) 0.0875(12) Uani 1 1 d . . .
H28A H 0.0710 0.3254 0.9711 0.131 Uiso 1 1 calc R . .
H28B H 0.2088 0.3440 1.0278 0.131 Uiso 1 1 calc R . .
H28C H 0.2074 0.2748 0.9432 0.131 Uiso 1 1 calc R . .
C29 C 0.2214(3) 0.19397(19) 0.6273(2) 0.0611(8) Uani 1 1 d . . .
H29 H 0.2245 0.1303 0.6170 0.073 Uiso 1 1 calc R . .
O6A O 0.73933(18) 0.50248(14) 0.83539(13) 0.0596(5) Uani 1 1 d . . .
C9A C 0.8515(3) 0.4615(3) 0.8865(2) 0.0765(10) Uani 1 1 d . . .
H9A1 H 0.9370 0.4876 0.8660 0.115 Uiso 1 1 calc R . .
H9A2 H 0.8518 0.3957 0.8759 0.115 Uiso 1 1 calc R . .
H9A3 H 0.8416 0.4736 0.9520 0.115 Uiso 1 1 calc R . .
H1N H 0.446(3) 0.4114(19) 0.526(2) 0.058(9) 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
O1 0.0408(11) 0.0555(10) 0.0474(9) 0.0220(8) 0.0026(8) -0.0066(8)
O2 0.0502(11) 0.0494(10) 0.0415(9) 0.0019(7) 0.0210(8) 0.0006(9)
C3 0.0397(14) 0.0324(11) 0.0320(11) 0.0019(9) 0.0006(10) 0.0007(10)
N1A 0.0407(12) 0.0522(13) 0.0322(10) -0.0065(9) 0.0101(9) 0.0103(11)
C5 0.0280(11) 0.0341(11) 0.0229(10) 0.0018(8) 0.0047(8) 0.0005(10)
C2A 0.0369(13) 0.0305(11) 0.0244(10) -0.0035(8) -0.0002(9) 0.0024(10)
C1A 0.0385(13) 0.0351(12) 0.0297(11) -0.0009(9) 0.0073(9) 0.0032(11)
O1A 0.152(3) 0.0402(12) 0.0873(16) -0.0199(10) 0.0249(16) -0.0031(13)
C9 0.0433(15) 0.0477(14) 0.0433(13) 0.0037(11) -0.0096(11) 0.0102(12)
N4A 0.0357(11) 0.0452(11) 0.0275(9) 0.0006(8) 0.0000(8) 0.0089(9)
C12 0.0393(14) 0.0377(12) 0.0301(11) 0.0016(9) 0.0031(10) 0.0002(11)
C13 0.0335(13) 0.0375(12) 0.0286(10) -0.0057(9) -0.0058(9) 0.0021(10)
O2A 0.1108(19) 0.0656(13) 0.0455(10) -0.0047(9) 0.0336(12) 0.0113(13)
C15 0.0516(16) 0.0399(13) 0.0319(11) 0.0034(10) 0.0020(10) 0.0139(12)
N2A 0.0632(15) 0.0402(12) 0.0400(11) -0.0075(9) 0.0031(10) 0.0049(11)
C17 0.0303(12) 0.0364(12) 0.0239(10) -0.0012(8) 0.0026(9) 0.0049(10)
C18 0.0496(16) 0.0404(13) 0.0411(12) 0.0106(10) -0.0028(11) 0.0022(12)
C19 0.0379(14) 0.0466(14) 0.0493(14) -0.0050(11) -0.0008(11) -0.0053(12)
C20 0.0367(15) 0.0681(17) 0.0409(13) 0.0030(12) -0.0018(11) 0.0054(13)
C21 0.0532(18) 0.0430(15) 0.0727(18) 0.0038(13) -0.0150(14) -0.0109(14)
C22 0.0376(13) 0.0446(13) 0.0318(11) -0.0086(10) -0.0085(10) 0.0082(11)
C23 0.0362(13) 0.0438(13) 0.0242(10) -0.0006(9) 0.0030(9) 0.0075(11)
C24 0.0311(13) 0.0458(14) 0.0415(12) -0.0052(11) -0.0006(10) 0.0017(11)
C25 0.0524(17) 0.0522(16) 0.0511(15) -0.0192(12) -0.0121(13) 0.0151(14)
C26 0.0484(17) 0.093(2) 0.0542(16) -0.0010(15) -0.0089(13) 0.0272(16)
C27 0.065(2) 0.0719(19) 0.0615(17) -0.0115(14) -0.0101(15) 0.0350(16)
C28 0.066(2) 0.085(2) 0.112(3) 0.060(2) 0.008(2) -0.0115(19)
C29 0.061(2) 0.0373(14) 0.084(2) -0.0162(14) -0.0232(16) 0.0067(14)
O6A 0.0311(10) 0.0859(14) 0.0618(12) 0.0116(10) 0.0007(8) 0.0010(10)
C9A 0.0365(17) 0.125(3) 0.0683(19) 0.0101(18) -0.0017(14) 0.0147(19)
_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
O1 C3 1.370(3) . ?
O1 C28 1.416(3) . ?
O2 C23 1.224(3) . ?
C3 C18 1.384(3) . ?
C3 C2A 1.405(3) . ?
N1A C23 1.339(3) . ?
N1A C22 1.406(3) . ?
N1A H1N 0.80(3) . ?
C5 C2A 1.511(3) . ?
C5 C1A 1.510(3) . ?
C5 C17 1.551(3) . ?
C5 H5 0.9800 . ?
C2A C12 1.382(3) . ?
C1A N2A 1.497(3) . ?
C1A C15 1.557(3) . ?
C1A H1A 0.9800 . ?
O1A N2A 1.214(3) . ?
C9 C24 1.370(3) . ?
C9 C18 1.385(4) . ?
C9 H9 0.9300 . ?
N4A C20 1.468(3) . ?
N4A C17 1.485(3) . ?
N4A C15 1.494(3) . ?
C12 C24 1.400(3) . ?
C12 H12 0.9300 . ?
C13 C19 1.386(3) . ?
C13 C22 1.384(3) . ?
C13 C17 1.512(3) . ?
O2A N2A 1.202(3) . ?
C15 C27 1.525(4) . ?
C15 H15 0.9800 . ?
C17 C23 1.556(3) . ?
C18 H18 0.9300 . ?
C19 C21 1.393(4) . ?
C19 H19 0.9300 . ?
C20 C26 1.509(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C29 1.388(4) . ?
C21 H21 0.9300 . ?
C22 C25 1.382(3) . ?
C24 O6A 1.369(3) . ?
C25 C29 1.379(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.517(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29 0.9300 . ?
O6A C9A 1.423(3) . ?
C9A H9A1 0.9600 . ?
C9A H9A2 0.9600 . ?
C9A H9A3 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
C3 O1 C28 117.7(2) . . ?
O1 C3 C18 123.68(19) . . ?
O1 C3 C2A 116.2(2) . . ?
C18 C3 C2A 120.1(2) . . ?
C23 N1A C22 112.4(2) . . ?
C23 N1A H1N 121(2) . . ?
C22 N1A H1N 126(2) . . ?
C2A C5 C1A 118.86(18) . . ?
C2A C5 C17 116.20(17) . . ?
C1A C5 C17 101.49(15) . . ?
C2A C5 H5 106.5 . . ?
C1A C5 H5 106.5 . . ?
C17 C5 H5 106.5 . . ?
C12 C2A C3 118.3(2) . . ?
C12 C2A C5 122.62(19) . . ?
C3 C2A C5 119.0(2) . . ?
N2A C1A C5 113.64(17) . . ?
N2A C1A C15 111.18(18) . . ?
C5 C1A C15 105.66(17) . . ?
N2A C1A H1A 108.7 . . ?
C5 C1A H1A 108.7 . . ?
C15 C1A H1A 108.7 . . ?
C24 C9 C18 120.4(2) . . ?
C24 C9 H9 119.8 . . ?
C18 C9 H9 119.8 . . ?
C20 N4A C17 117.52(18) . . ?
C20 N4A C15 107.82(18) . . ?
C17 N4A C15 106.86(16) . . ?
C2A C12 C24 121.4(2) . . ?
C2A C12 H12 119.3 . . ?
C24 C12 H12 119.3 . . ?
C19 C13 C22 119.3(2) . . ?
C19 C13 C17 131.6(2) . . ?
C22 C13 C17 108.82(19) . . ?
N4A C15 C27 105.0(2) . . ?
N4A C15 C1A 105.77(16) . . ?
C27 C15 C1A 118.68(19) . . ?
N4A C15 H15 109.0 . . ?
C27 C15 H15 109.0 . . ?
C1A C15 H15 109.0 . . ?
O2A N2A O1A 123.3(2) . . ?
O2A N2A C1A 120.4(2) . . ?
O1A N2A C1A 116.2(2) . . ?
N4A C17 C13 117.42(18) . . ?
N4A C17 C5 104.15(16) . . ?
C13 C17 C5 114.95(16) . . ?
N4A C17 C23 104.42(16) . . ?
C13 C17 C23 101.57(16) . . ?
C5 C17 C23 114.22(18) . . ?
C3 C18 C9 120.5(2) . . ?
C3 C18 H18 119.8 . . ?
C9 C18 H18 119.8 . . ?
C13 C19 C21 119.2(2) . . ?
C13 C19 H19 120.4 . . ?
C21 C19 H19 120.4 . . ?
N4A C20 C26 102.5(2) . . ?
N4A C20 H20A 111.3 . . ?
C26 C20 H20A 111.3 . . ?
N4A C20 H20B 111.3 . . ?
C26 C20 H20B 111.3 . . ?
H20A C20 H20B 109.2 . . ?
C29 C21 C19 120.1(3) . . ?
C29 C21 H21 120.0 . . ?
C19 C21 H21 120.0 . . ?
C25 C22 C13 122.2(2) . . ?
C25 C22 N1A 128.3(2) . . ?
C13 C22 N1A 109.4(2) . . ?
O2 C23 N1A 127.2(2) . . ?
O2 C23 C17 125.01(19) . . ?
N1A C23 C17 107.7(2) . . ?
C9 C24 O6A 124.9(2) . . ?
C9 C24 C12 119.3(2) . . ?
O6A C24 C12 115.8(2) . . ?
C29 C25 C22 117.9(2) . . ?
C29 C25 H25 121.1 . . ?
C22 C25 H25 121.1 . . ?
C20 C26 C27 102.3(2) . . ?
C20 C26 H26A 111.3 . . ?
C27 C26 H26A 111.3 . . ?
C20 C26 H26B 111.3 . . ?
C27 C26 H26B 111.3 . . ?
H26A C26 H26B 109.2 . . ?
C26 C27 C15 104.4(2) . . ?
C26 C27 H27A 110.9 . . ?
C15 C27 H27A 110.9 . . ?
C26 C27 H27B 110.9 . . ?
C15 C27 H27B 110.9 . . ?
H27A C27 H27B 108.9 . . ?
O1 C28 H28A 109.5 . . ?
O1 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O1 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C29 C21 121.1(3) . . ?
C25 C29 H29 119.4 . . ?
C21 C29 H29 119.4 . . ?
C24 O6A C9A 116.6(2) . . ?
O6A C9A H9A1 109.5 . . ?
O6A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
O6A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 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
C28 O1 C3 C18 -11.3(4) . . . . ?
C28 O1 C3 C2A 170.4(2) . . . . ?
O1 C3 C2A C12 178.05(18) . . . . ?
C18 C3 C2A C12 -0.3(3) . . . . ?
O1 C3 C2A C5 -3.2(3) . . . . ?
C18 C3 C2A C5 178.47(19) . . . . ?
C1A C5 C2A C12 -47.8(3) . . . . ?
C17 C5 C2A C12 73.8(3) . . . . ?
C1A C5 C2A C3 133.5(2) . . . . ?
C17 C5 C2A C3 -104.9(2) . . . . ?
C2A C5 C1A N2A -76.6(2) . . . . ?
C17 C5 C1A N2A 154.57(19) . . . . ?
C2A C5 C1A C15 161.20(18) . . . . ?
C17 C5 C1A C15 32.4(2) . . . . ?
C3 C2A C12 C24 0.5(3) . . . . ?
C5 C2A C12 C24 -178.22(19) . . . . ?
C20 N4A C15 C27 -11.5(2) . . . . ?
C17 N4A C15 C27 -138.69(19) . . . . ?
C20 N4A C15 C1A 114.8(2) . . . . ?
C17 N4A C15 C1A -12.4(2) . . . . ?
N2A C1A C15 N4A -137.16(19) . . . . ?
C5 C1A C15 N4A -13.4(2) . . . . ?
N2A C1A C15 C27 -19.7(3) . . . . ?
C5 C1A C15 C27 104.1(2) . . . . ?
C5 C1A N2A O2A -13.9(3) . . . . ?
C15 C1A N2A O2A 105.2(3) . . . . ?
C5 C1A N2A O1A 169.9(2) . . . . ?
C15 C1A N2A O1A -71.0(3) . . . . ?
C20 N4A C17 C13 40.1(3) . . . . ?
C15 N4A C17 C13 161.33(18) . . . . ?
C20 N4A C17 C5 -88.3(2) . . . . ?
C15 N4A C17 C5 33.0(2) . . . . ?
C20 N4A C17 C23 151.62(18) . . . . ?
C15 N4A C17 C23 -87.16(18) . . . . ?
C19 C13 C17 N4A -74.4(3) . . . . ?
C22 C13 C17 N4A 110.9(2) . . . . ?
C19 C13 C17 C5 48.6(3) . . . . ?
C22 C13 C17 C5 -126.1(2) . . . . ?
C19 C13 C17 C23 172.5(2) . . . . ?
C22 C13 C17 C23 -2.2(2) . . . . ?
C2A C5 C17 N4A -170.86(17) . . . . ?
C1A C5 C17 N4A -40.4(2) . . . . ?
C2A C5 C17 C13 59.3(3) . . . . ?
C1A C5 C17 C13 -170.27(18) . . . . ?
C2A C5 C17 C23 -57.6(2) . . . . ?
C1A C5 C17 C23 72.9(2) . . . . ?
O1 C3 C18 C9 -178.2(2) . . . . ?
C2A C3 C18 C9 0.0(3) . . . . ?
C24 C9 C18 C3 0.1(4) . . . . ?
C22 C13 C19 C21 -1.2(3) . . . . ?
C17 C13 C19 C21 -175.5(2) . . . . ?
C17 N4A C20 C26 154.44(18) . . . . ?
C15 N4A C20 C26 33.7(2) . . . . ?
C13 C19 C21 C29 -0.7(4) . . . . ?
C19 C13 C22 C25 2.0(3) . . . . ?
C17 C13 C22 C25 177.5(2) . . . . ?
C19 C13 C22 N1A -175.6(2) . . . . ?
C17 C13 C22 N1A -0.1(2) . . . . ?
C23 N1A C22 C25 -174.5(2) . . . . ?
C23 N1A C22 C13 2.9(3) . . . . ?
C22 N1A C23 O2 179.6(2) . . . . ?
C22 N1A C23 C17 -4.3(2) . . . . ?
N4A C17 C23 O2 57.5(3) . . . . ?
C13 C17 C23 O2 -179.9(2) . . . . ?
C5 C17 C23 O2 -55.6(3) . . . . ?
N4A C17 C23 N1A -118.63(19) . . . . ?
C13 C17 C23 N1A 3.9(2) . . . . ?
C5 C17 C23 N1A 128.27(19) . . . . ?
C18 C9 C24 O6A 179.8(2) . . . . ?
C18 C9 C24 C12 0.1(4) . . . . ?
C2A C12 C24 C9 -0.4(3) . . . . ?
C2A C12 C24 O6A 179.90(19) . . . . ?
C13 C22 C25 C29 -0.9(4) . . . . ?
N1A C22 C25 C29 176.2(2) . . . . ?
N4A C20 C26 C27 -42.4(3) . . . . ?
C20 C26 C27 C15 35.5(3) . . . . ?
N4A C15 C27 C26 -15.2(3) . . . . ?
C1A C15 C27 C26 -133.1(2) . . . . ?
C22 C25 C29 C21 -1.0(4) . . . . ?
C19 C21 C29 C25 1.8(4) . . . . ?
C9 C24 O6A C9A 2.5(4) . . . . ?
C12 C24 O6A C9A -177.8(2) . . . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 24.97
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.342
_refine_diff_density_min -0.191
_refine_diff_density_rms 0.044
data_4omepg_acta
_database_code_depnum_ccdc_archive 'CCDC 802308'
#TrackingRef '4omepg acta.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C24 H21 N3 O4 '
_chemical_formula_sum 'C24 H21 N3 O4 '
_chemical_formula_weight 415.44
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 'I 2/a'
_symmetry_space_group_name_Hall '-I 2/a'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
_cell_length_a 17.888(4)
_cell_length_b 11.260(3)
_cell_length_c 21.426(2)
_cell_angle_alpha 90.00
_cell_angle_beta 108.65(4)
_cell_angle_gamma 90.00
_cell_volume 4089.0(15)
_cell_formula_units_Z 8
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 25
_cell_measurement_theta_min 2
_cell_measurement_theta_max 25
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.26
_exptl_crystal_size_mid 0.23
_exptl_crystal_size_min 0.21
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.350
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1744
_exptl_absorpt_coefficient_mu 0.094
_exptl_absorpt_correction_type psi-scan
_exptl_absorpt_correction_T_min 0.9760
_exptl_absorpt_correction_T_max 0.9800
_exptl_absorpt_process_details '(North et al., 1968)'
_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 MACH3-Nonius
_diffrn_measurement_method \w-2\q
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time 60
_diffrn_standards_decay_% 0
_diffrn_reflns_number 9624
_diffrn_reflns_av_R_equivalents 0.4799
_diffrn_reflns_av_sigmaI/netI 0.3176
_diffrn_reflns_limit_h_min -21
_diffrn_reflns_limit_h_max 21
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 1
_diffrn_reflns_limit_l_min -25
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_theta_min 2.01
_diffrn_reflns_theta_max 24.97
_reflns_number_total 3499
_reflns_number_gt 2221
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CAD4 Express (Enraf Nonius, (1994)'
_computing_cell_refinement 'CAD4 Express (Enraf Nonius, (1994)'
_computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1996)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'PLATON (Spek, 2009)'
_computing_publication_material SHELXL-97
_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.
;
_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^)+(0.0618P)^2^+0.2249P] 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 SHELXL
_refine_ls_extinction_coef 0.0011(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 3499
_refine_ls_number_parameters 289
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1943
_refine_ls_R_factor_gt 0.0770
_refine_ls_wR_factor_ref 0.2173
_refine_ls_wR_factor_gt 0.1877
_refine_ls_goodness_of_fit_ref 1.160
_refine_ls_restrained_S_all 1.160
_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
H2 H 0.010(3) 0.151(3) 0.0796(19) 0.050(10) Uiso 1 1 d . . .
H1 H -0.002(3) 0.512(4) 0.063(2) 0.050(10) Uiso 1 1 d . . .
O1 O 0.06185(15) 0.3632(2) 0.00584(11) 0.0536(7) Uani 1 1 d . . .
O2 O 0.26050(18) 0.0375(3) 0.15594(18) 0.0753(9) Uani 1 1 d . . .
C001 C 0.17903(17) 0.2595(2) 0.13147(13) 0.0351(7) Uani 1 1 d . . .
H001 H 0.1993 0.2191 0.1741 0.042 Uiso 1 1 calc R . .
N2 N 0.06187(17) 0.1531(2) 0.09922(15) 0.0468(7) Uani 1 1 d . . .
C002 C 0.22647(17) 0.3727(3) 0.13644(15) 0.0398(7) Uani 1 1 d . . .
C003 C 0.0132(2) 0.4625(4) 0.2565(2) 0.0597(10) Uani 1 1 d . . .
H003 H -0.0033 0.5086 0.2856 0.072 Uiso 1 1 calc R . .
C004 C 0.18393(18) 0.1707(3) 0.07875(15) 0.0407(7) Uani 1 1 d . . .
H004 H 0.1897 0.2145 0.0410 0.049 Uiso 1 1 calc R . .
O4 O 0.3477(2) 0.6906(3) 0.14068(18) 0.0802(9) Uani 1 1 d . . .
C005 C 0.10892(18) -0.0315(3) 0.05955(15) 0.0409(7) Uani 1 1 d . . .
N1 N 0.25391(17) 0.0928(3) 0.10624(17) 0.0570(9) Uani 1 1 d . . .
C006 C 0.10352(18) 0.1024(3) 0.05646(15) 0.0421(7) Uani 1 1 d . . .
H006 H 0.0749 0.1252 0.0109 0.051 Uiso 1 1 calc R . .
C007 C 0.2370(2) 0.4483(3) 0.18873(19) 0.0549(9) Uani 1 1 d . . .
H007 H 0.2172 0.4279 0.2224 0.066 Uiso 1 1 calc R . .
N3 N 0.02074(17) 0.4547(3) 0.08543(16) 0.0489(7) Uani 1 1 d . . .
C008 C 0.0768(2) 0.2857(3) 0.23524(18) 0.0509(8) Uani 1 1 d . . .
H008 H 0.1024 0.2139 0.2493 0.061 Uiso 1 1 calc R . .
C009 C 0.06451(17) 0.3260(3) 0.17190(16) 0.0414(7) Uani 1 1 d . . .
C010 C 0.02644(18) 0.4330(3) 0.15132(17) 0.0440(7) Uani 1 1 d . . .
C011 C 0.2613(3) 0.4059(4) 0.0900(2) 0.0718(12) Uani 1 1 d . . .
H011 H 0.2567 0.3549 0.0548 0.086 Uiso 1 1 calc R . .
C012 C 0.05632(18) 0.3674(3) 0.06152(16) 0.0417(7) Uani 1 1 d . . .
C013 C 0.08901(17) 0.2740(3) 0.11642(15) 0.0393(7) Uani 1 1 d . . .
C014 C 0.3080(2) 0.5868(3) 0.1429(2) 0.0576(9) Uani 1 1 d . . .
C015 C 0.0004(2) 0.5032(3) 0.1933(2) 0.0561(9) Uani 1 1 d . . .
H015 H -0.0249 0.5751 0.1794 0.067 Uiso 1 1 calc R . .
C016 C 0.1309(2) -0.0921(3) 0.01176(19) 0.0569(9) Uani 1 1 d . . .
H016 H 0.1403 -0.0499 -0.0223 0.068 Uiso 1 1 calc R . .
O3 O 0.3022(2) 0.0899(4) 0.0772(2) 0.1049(14) Uani 1 1 d . . .
C017 C 0.0933(3) -0.0974(3) 0.1083(2) 0.0588(10) Uani 1 1 d . . .
H017 H 0.0778 -0.0594 0.1407 0.071 Uiso 1 1 calc R . .
C018 C 0.2780(2) 0.5576(3) 0.1920(2) 0.0635(11) Uani 1 1 d . . .
H018 H 0.2843 0.6089 0.2274 0.076 Uiso 1 1 calc R . .
C019 C 0.0500(2) 0.3550(4) 0.27777(19) 0.0587(10) Uani 1 1 d . . .
H019 H 0.0568 0.3289 0.3204 0.070 Uiso 1 1 calc R . .
C020 C 0.1006(3) -0.2203(4) 0.1090(2) 0.0714(12) Uani 1 1 d . . .
H020 H 0.0894 -0.2641 0.1417 0.086 Uiso 1 1 calc R . .
C021 C 0.1239(2) -0.2774(3) 0.0623(2) 0.0665(11) Uani 1 1 d . . .
H021 H 0.1294 -0.3596 0.0636 0.080 Uiso 1 1 calc R . .
C022 C 0.1392(3) -0.2142(4) 0.0141(2) 0.0672(11) Uani 1 1 d . . .
H022 H 0.1553 -0.2531 -0.0177 0.081 Uiso 1 1 calc R . .
C023 C 0.3021(3) 0.5094(5) 0.0931(2) 0.0805(14) Uani 1 1 d . . .
H023 H 0.3256 0.5267 0.0612 0.097 Uiso 1 1 calc R . .
C024 C 0.3488(3) 0.7792(4) 0.1855(4) 0.0972(18) Uani 1 1 d . . .
H02A H 0.3783 0.8458 0.1779 0.117 Uiso 1 1 calc R . .
H02B H 0.3732 0.7499 0.2294 0.117 Uiso 1 1 calc R . .
H02C H 0.2958 0.8037 0.1803 0.117 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 0.0621(14) 0.0498(14) 0.0462(13) 0.0055(10) 0.0134(10) 0.0150(11)
O2 0.0676(17) 0.0541(17) 0.085(2) -0.0024(15) -0.0022(15) 0.0196(13)
C001 0.0413(15) 0.0294(15) 0.0348(14) 0.0026(11) 0.0124(11) 0.0015(11)
N2 0.0394(15) 0.0341(15) 0.0668(17) -0.0057(12) 0.0170(13) -0.0014(11)
C002 0.0396(15) 0.0313(16) 0.0449(16) 0.0025(12) 0.0084(12) 0.0004(12)
C003 0.061(2) 0.060(2) 0.069(2) -0.0183(18) 0.0355(18) -0.0123(18)
C004 0.0447(16) 0.0372(17) 0.0408(15) -0.0036(12) 0.0144(12) -0.0021(12)
O4 0.084(2) 0.0549(18) 0.101(2) -0.0028(16) 0.0292(17) -0.0193(15)
C005 0.0407(15) 0.0343(17) 0.0451(16) -0.0022(12) 0.0099(12) -0.0028(12)
N1 0.0447(16) 0.0584(19) 0.063(2) -0.0280(17) 0.0101(14) 0.0036(13)
C006 0.0437(17) 0.0381(17) 0.0404(16) -0.0019(12) 0.0076(12) -0.0011(13)
C007 0.0569(19) 0.049(2) 0.058(2) -0.0142(16) 0.0181(15) -0.0091(16)
N3 0.0526(16) 0.0384(16) 0.0543(16) 0.0049(13) 0.0150(13) 0.0115(13)
C008 0.0502(18) 0.0488(19) 0.059(2) 0.0027(15) 0.0246(15) -0.0055(15)
C009 0.0366(15) 0.0393(17) 0.0512(17) -0.0019(13) 0.0179(12) -0.0048(12)
C010 0.0396(15) 0.0348(17) 0.0588(19) -0.0023(13) 0.0176(13) -0.0015(12)
C011 0.098(3) 0.064(3) 0.064(2) -0.0107(19) 0.041(2) -0.031(2)
C012 0.0400(15) 0.0347(17) 0.0475(18) -0.0011(13) 0.0098(13) 0.0024(12)
C013 0.0414(16) 0.0323(16) 0.0447(16) -0.0011(12) 0.0143(12) -0.0019(12)
C014 0.054(2) 0.0388(19) 0.079(3) 0.0110(17) 0.0205(18) -0.0021(15)
C015 0.056(2) 0.0438(19) 0.075(2) -0.0105(17) 0.0301(17) -0.0002(15)
C016 0.070(2) 0.047(2) 0.060(2) -0.0108(16) 0.0303(18) -0.0139(16)
O3 0.0617(18) 0.156(4) 0.104(3) -0.054(3) 0.0364(18) 0.016(2)
C017 0.079(3) 0.044(2) 0.060(2) 0.0003(16) 0.0327(19) 0.0008(17)
C018 0.058(2) 0.052(2) 0.072(2) -0.0240(18) 0.0091(18) 0.0036(18)
C019 0.056(2) 0.071(3) 0.056(2) -0.0057(18) 0.0282(16) -0.0151(19)
C020 0.091(3) 0.046(2) 0.080(3) 0.013(2) 0.031(2) -0.007(2)
C021 0.061(2) 0.0361(19) 0.099(3) -0.0035(19) 0.021(2) -0.0010(17)
C022 0.072(2) 0.046(2) 0.093(3) -0.024(2) 0.039(2) -0.0063(18)
C023 0.106(4) 0.070(3) 0.077(3) -0.010(2) 0.044(3) -0.039(3)
C024 0.077(3) 0.052(3) 0.149(5) -0.016(3) 0.019(3) -0.010(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
O1 C012 1.229(4) . ?
O2 N1 1.207(5) . ?
C001 C002 1.516(4) . ?
C001 C004 1.532(4) . ?
C001 C013 1.546(4) . ?
C001 H001 0.9800 . ?
N2 C013 1.452(4) . ?
N2 C006 1.469(4) . ?
N2 H2 0.89(5) . ?
C002 C007 1.371(5) . ?
C002 C011 1.384(5) . ?
C003 C015 1.376(6) . ?
C003 C019 1.384(6) . ?
C003 H003 0.9300 . ?
C004 N1 1.487(5) . ?
C004 C006 1.565(4) . ?
C004 H004 0.9800 . ?
O4 C014 1.376(5) . ?
O4 C024 1.380(7) . ?
C005 C017 1.381(5) . ?
C005 C016 1.388(5) . ?
C005 C006 1.511(5) . ?
N1 O3 1.215(5) . ?
C006 H006 0.9800 . ?
C007 C018 1.423(6) . ?
C007 H007 0.9300 . ?
N3 C012 1.357(5) . ?
N3 C010 1.404(5) . ?
N3 H1 0.82(5) . ?
C008 C009 1.380(5) . ?
C008 C019 1.396(5) . ?
C008 H008 0.9300 . ?
C009 C010 1.385(5) . ?
C009 C013 1.510(4) . ?
C010 C015 1.386(5) . ?
C011 C023 1.366(6) . ?
C011 H011 0.9300 . ?
C012 C013 1.547(4) . ?
C014 C023 1.355(7) . ?
C014 C018 1.367(6) . ?
C015 H015 0.9300 . ?
C016 C022 1.382(6) . ?
C016 H016 0.9300 . ?
C017 C020 1.390(6) . ?
C017 H017 0.9300 . ?
C018 H018 0.9300 . ?
C019 H019 0.9300 . ?
C020 C021 1.362(7) . ?
C020 H020 0.9300 . ?
C021 C022 1.353(7) . ?
C021 H021 0.9300 . ?
C022 H022 0.9300 . ?
C023 H023 0.9300 . ?
C024 H02A 0.9600 . ?
C024 H02B 0.9600 . ?
C024 H02C 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
C002 C001 C004 116.0(2) . . ?
C002 C001 C013 116.6(2) . . ?
C004 C001 C013 102.5(2) . . ?
C002 C001 H001 107.0 . . ?
C004 C001 H001 107.0 . . ?
C013 C001 H001 107.0 . . ?
C013 N2 C006 109.1(2) . . ?
C013 N2 H2 111(2) . . ?
C006 N2 H2 111(2) . . ?
C007 C002 C011 116.4(3) . . ?
C007 C002 C001 120.5(3) . . ?
C011 C002 C001 123.2(3) . . ?
C015 C003 C019 121.8(3) . . ?
C015 C003 H003 119.1 . . ?
C019 C003 H003 119.1 . . ?
N1 C004 C001 109.4(2) . . ?
N1 C004 C006 113.9(3) . . ?
C001 C004 C006 106.4(2) . . ?
N1 C004 H004 109.0 . . ?
C001 C004 H004 109.0 . . ?
C006 C004 H004 109.0 . . ?
C014 O4 C024 119.0(4) . . ?
C017 C005 C016 117.9(3) . . ?
C017 C005 C006 122.9(3) . . ?
C016 C005 C006 119.2(3) . . ?
O2 N1 O3 123.6(4) . . ?
O2 N1 C004 119.1(3) . . ?
O3 N1 C004 117.3(4) . . ?
N2 C006 C005 113.5(3) . . ?
N2 C006 C004 102.6(2) . . ?
C005 C006 C004 116.0(3) . . ?
N2 C006 H006 108.1 . . ?
C005 C006 H006 108.1 . . ?
C004 C006 H006 108.1 . . ?
C002 C007 C018 120.8(4) . . ?
C002 C007 H007 119.6 . . ?
C018 C007 H007 119.6 . . ?
C012 N3 C010 111.2(3) . . ?
C012 N3 H1 123(3) . . ?
C010 N3 H1 125(3) . . ?
C009 C008 C019 118.6(3) . . ?
C009 C008 H008 120.7 . . ?
C019 C008 H008 120.7 . . ?
C008 C009 C010 120.4(3) . . ?
C008 C009 C013 130.7(3) . . ?
C010 C009 C013 108.9(3) . . ?
C009 C010 C015 121.5(3) . . ?
C009 C010 N3 110.0(3) . . ?
C015 C010 N3 128.5(3) . . ?
C023 C011 C002 123.5(4) . . ?
C023 C011 H011 118.3 . . ?
C002 C011 H011 118.3 . . ?
O1 C012 N3 126.0(3) . . ?
O1 C012 C013 125.7(3) . . ?
N3 C012 C013 108.3(3) . . ?
N2 C013 C009 113.9(3) . . ?
N2 C013 C001 101.3(2) . . ?
C009 C013 C001 114.9(2) . . ?
N2 C013 C012 115.5(3) . . ?
C009 C013 C012 101.6(2) . . ?
C001 C013 C012 110.2(2) . . ?
C023 C014 C018 120.1(4) . . ?
C023 C014 O4 115.5(4) . . ?
C018 C014 O4 124.4(4) . . ?
C003 C015 C010 117.7(3) . . ?
C003 C015 H015 121.2 . . ?
C010 C015 H015 121.2 . . ?
C022 C016 C005 120.9(4) . . ?
C022 C016 H016 119.5 . . ?
C005 C016 H016 119.5 . . ?
C005 C017 C020 120.1(4) . . ?
C005 C017 H017 120.0 . . ?
C020 C017 H017 120.0 . . ?
C014 C018 C007 119.5(4) . . ?
C014 C018 H018 120.2 . . ?
C007 C018 H018 120.2 . . ?
C003 C019 C008 120.0(3) . . ?
C003 C019 H019 120.0 . . ?
C008 C019 H019 120.0 . . ?
C021 C020 C017 120.8(4) . . ?
C021 C020 H020 119.6 . . ?
C017 C020 H020 119.6 . . ?
C022 C021 C020 119.7(4) . . ?
C022 C021 H021 120.1 . . ?
C020 C021 H021 120.1 . . ?
C021 C022 C016 120.4(4) . . ?
C021 C022 H022 119.8 . . ?
C016 C022 H022 119.8 . . ?
C014 C023 C011 119.6(4) . . ?
C014 C023 H023 120.2 . . ?
C011 C023 H023 120.2 . . ?
O4 C024 H02A 109.5 . . ?
O4 C024 H02B 109.5 . . ?
H02A C024 H02B 109.5 . . ?
O4 C024 H02C 109.5 . . ?
H02A C024 H02C 109.5 . . ?
H02B C024 H02C 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
C004 C001 C002 C007 -168.9(3) . . . . ?
C013 C001 C002 C007 70.3(4) . . . . ?
C004 C001 C002 C011 11.0(5) . . . . ?
C013 C001 C002 C011 -109.9(4) . . . . ?
C002 C001 C004 N1 86.0(3) . . . . ?
C013 C001 C004 N1 -145.8(3) . . . . ?
C002 C001 C004 C006 -150.5(2) . . . . ?
C013 C001 C004 C006 -22.3(3) . . . . ?
C001 C004 N1 O2 55.8(4) . . . . ?
C006 C004 N1 O2 -63.1(4) . . . . ?
C001 C004 N1 O3 -123.3(3) . . . . ?
C006 C004 N1 O3 117.8(4) . . . . ?
C013 N2 C006 C005 154.5(3) . . . . ?
C013 N2 C006 C004 28.6(3) . . . . ?
C017 C005 C006 N2 -14.3(5) . . . . ?
C016 C005 C006 N2 166.0(3) . . . . ?
C017 C005 C006 C004 104.2(4) . . . . ?
C016 C005 C006 C004 -75.5(4) . . . . ?
N1 C004 C006 N2 118.4(3) . . . . ?
C001 C004 C006 N2 -2.2(3) . . . . ?
N1 C004 C006 C005 -5.9(4) . . . . ?
C001 C004 C006 C005 -126.5(3) . . . . ?
C011 C002 C007 C018 3.4(5) . . . . ?
C001 C002 C007 C018 -176.7(3) . . . . ?
C019 C008 C009 C010 0.1(5) . . . . ?
C019 C008 C009 C013 177.4(3) . . . . ?
C008 C009 C010 C015 0.7(5) . . . . ?
C013 C009 C010 C015 -177.2(3) . . . . ?
C008 C009 C010 N3 -179.8(3) . . . . ?
C013 C009 C010 N3 2.3(3) . . . . ?
C012 N3 C010 C009 -2.1(4) . . . . ?
C012 N3 C010 C015 177.3(3) . . . . ?
C007 C002 C011 C023 -2.2(7) . . . . ?
C001 C002 C011 C023 177.9(4) . . . . ?
C010 N3 C012 O1 -178.8(3) . . . . ?
C010 N3 C012 C013 1.1(3) . . . . ?
C006 N2 C013 C009 -167.0(3) . . . . ?
C006 N2 C013 C001 -43.1(3) . . . . ?
C006 N2 C013 C012 76.0(3) . . . . ?
C008 C009 C013 N2 56.0(4) . . . . ?
C010 C009 C013 N2 -126.4(3) . . . . ?
C008 C009 C013 C001 -60.2(4) . . . . ?
C010 C009 C013 C001 117.4(3) . . . . ?
C008 C009 C013 C012 -179.1(3) . . . . ?
C010 C009 C013 C012 -1.6(3) . . . . ?
C002 C001 C013 N2 166.4(3) . . . . ?
C004 C001 C013 N2 38.7(3) . . . . ?
C002 C001 C013 C009 -70.3(3) . . . . ?
C004 C001 C013 C009 161.9(2) . . . . ?
C002 C001 C013 C012 43.7(3) . . . . ?
C004 C001 C013 C012 -84.1(3) . . . . ?
O1 C012 C013 N2 -56.0(4) . . . . ?
N3 C012 C013 N2 124.1(3) . . . . ?
O1 C012 C013 C009 -179.8(3) . . . . ?
N3 C012 C013 C009 0.3(3) . . . . ?
O1 C012 C013 C001 57.9(4) . . . . ?
N3 C012 C013 C001 -122.0(3) . . . . ?
C024 O4 C014 C023 173.0(5) . . . . ?
C024 O4 C014 C018 -9.1(6) . . . . ?
C019 C003 C015 C010 -0.7(5) . . . . ?
C009 C010 C015 C003 -0.3(5) . . . . ?
N3 C010 C015 C003 -179.7(3) . . . . ?
C017 C005 C016 C022 -1.9(6) . . . . ?
C006 C005 C016 C022 177.8(4) . . . . ?
C016 C005 C017 C020 0.7(6) . . . . ?
C006 C005 C017 C020 -178.9(4) . . . . ?
C023 C014 C018 C007 -3.2(6) . . . . ?
O4 C014 C018 C007 179.1(4) . . . . ?
C002 C007 C018 C014 -0.9(6) . . . . ?
C015 C003 C019 C008 1.4(5) . . . . ?
C009 C008 C019 C003 -1.1(5) . . . . ?
C005 C017 C020 C021 0.7(7) . . . . ?
C017 C020 C021 C022 -1.0(7) . . . . ?
C020 C021 C022 C016 -0.2(7) . . . . ?
C005 C016 C022 C021 1.7(7) . . . . ?
C018 C014 C023 C011 4.4(8) . . . . ?
O4 C014 C023 C011 -177.7(5) . . . . ?
C002 C011 C023 C014 -1.7(9) . . . . ?
_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full 24.97
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max 0.634
_refine_diff_density_min -0.232
_refine_diff_density_rms 0.050
# Attachment 'ppg acta.cif'
#=========================================================================
data_ppg_acta
_database_code_depnum_ccdc_archive 'CCDC 802309'
#TrackingRef 'ppg acta.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C23 H19 N3 O3'
_chemical_formula_sum 'C23 H19 N3 O3'
_chemical_formula_weight 385.41
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 triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 7.681(4)
_cell_length_b 11.655(5)
_cell_length_c 12.824(3)
_cell_angle_alpha 64.68(3)
_cell_angle_beta 76.11(4)
_cell_angle_gamma 71.43(3)
_cell_volume 976.5(8)
_cell_formula_units_Z 2
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 25
_cell_measurement_theta_min 2
_cell_measurement_theta_max 25
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.26
_exptl_crystal_size_mid 0.23
_exptl_crystal_size_min 0.21
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.311
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 404
_exptl_absorpt_coefficient_mu 0.089
_exptl_absorpt_correction_type psi-scan
_exptl_absorpt_correction_T_min 0.9760
_exptl_absorpt_correction_T_max 0.9800
_exptl_absorpt_process_details '(North et al., 1968)'
_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 MACH3-Nonius
_diffrn_measurement_method \w-2\q
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time 60
_diffrn_standards_decay_% 0
_diffrn_reflns_number 2367
_diffrn_reflns_av_R_equivalents 0.0173
_diffrn_reflns_av_sigmaI/netI 0.0158
_diffrn_reflns_limit_h_min -1
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.10
_diffrn_reflns_theta_max 19.98
_reflns_number_total 1820
_reflns_number_gt 1584
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CAD4 Express (Enraf Nonius, (1994)'
_computing_cell_refinement 'CAD4 Express (Enraf Nonius, (1994)'
_computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1996)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'PLATON (Spek, 2009)'
_computing_publication_material SHELXL-97
_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.
;
_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^)+(0.0618P)^2^+0.2249P] 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 SHELXL
_refine_ls_extinction_coef 0.004(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 1820
_refine_ls_number_parameters 271
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1242
_refine_ls_R_factor_gt 0.1054
_refine_ls_wR_factor_ref 0.4954
_refine_ls_wR_factor_gt 0.4769
_refine_ls_goodness_of_fit_ref 1.265
_refine_ls_restrained_S_all 1.265
_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
C10 C 0.785(2) 0.2672(13) 0.2638(12) 0.035(4) Uani 1 1 d . . .
C7 C 0.529(2) 0.3868(14) 0.3509(14) 0.041(4) Uani 1 1 d . . .
H7 H 0.5524 0.3424 0.4324 0.050 Uiso 1 1 calc R . .
C18 C 0.636(2) 0.1135(14) 0.2387(13) 0.035(4) Uani 1 1 d . . .
C15 C 1.244(2) 0.1200(16) 0.1493(14) 0.044(4) Uani 1 1 d . . .
H15 H 1.3343 0.0439 0.1796 0.053 Uiso 1 1 calc R . .
C13 C 1.127(2) 0.3129(16) -0.0129(14) 0.046(5) Uani 1 1 d . . .
H13 H 1.1430 0.3671 -0.0909 0.055 Uiso 1 1 calc R . .
C16 C 1.089(2) 0.1540(15) 0.2167(13) 0.040(4) Uani 1 1 d . . .
C8 C 0.459(2) 0.2955(15) 0.3208(14) 0.040(4) Uani 1 1 d . . .
H8 H 0.4392 0.2201 0.3920 0.048 Uiso 1 1 calc R . .
C12 C 0.966(2) 0.3438(15) 0.0560(13) 0.041(4) Uani 1 1 d . . .
H12 H 0.8724 0.4178 0.0248 0.049 Uiso 1 1 calc R . .
C17 C 0.864(2) 0.1501(14) 0.3719(15) 0.036(4) Uani 1 1 d . . .
C9 C 0.612(2) 0.2475(15) 0.2381(13) 0.041(4) Uani 1 1 d . . .
H9 H 0.5893 0.3106 0.1593 0.049 Uiso 1 1 calc R . .
C11 C 0.9450(19) 0.2633(14) 0.1719(13) 0.035(4) Uani 1 1 d . . .
C23 C 0.727(2) 0.0898(17) 0.1385(15) 0.051(5) Uani 1 1 d . . .
H23 H 0.7656 0.1572 0.0736 0.061 Uiso 1 1 calc R . .
C21 C 0.703(3) -0.1316(18) 0.2300(19) 0.065(6) Uani 1 1 d . . .
H21 H 0.7247 -0.2136 0.2275 0.078 Uiso 1 1 calc R . .
C14 C 1.263(2) 0.2027(18) 0.0330(15) 0.053(5) Uani 1 1 d . . .
H14 H 1.3705 0.1830 -0.0147 0.064 Uiso 1 1 calc R . .
C19 C 0.585(2) 0.0116(17) 0.3318(15) 0.050(5) Uani 1 1 d . . .
H19 H 0.5300 0.0241 0.4003 0.059 Uiso 1 1 calc R . .
C22 C 0.762(2) -0.033(2) 0.1349(18) 0.059(5) Uani 1 1 d . . .
H22 H 0.8239 -0.0478 0.0684 0.071 Uiso 1 1 calc R . .
C5 C 0.408(3) 0.6265(17) 0.2308(17) 0.063(6) Uani 1 1 d . . .
H5 H 0.4942 0.6152 0.1689 0.076 Uiso 1 1 calc R . .
C3 C 0.165(3) 0.767(2) 0.306(2) 0.077(6) Uani 1 1 d . . .
H3 H 0.0871 0.8495 0.2954 0.092 Uiso 1 1 calc R . .
C6 C 0.401(2) 0.5223(15) 0.3351(15) 0.041(4) Uani 1 1 d . . .
C20 C 0.612(3) -0.1107(18) 0.3283(17) 0.061(5) Uani 1 1 d . . .
H20 H 0.5695 -0.1771 0.3918 0.073 Uiso 1 1 calc R . .
C1 C 0.275(3) 0.543(2) 0.4257(17) 0.067(6) Uani 1 1 d . . .
H1 H 0.2696 0.4740 0.4976 0.080 Uiso 1 1 calc R . .
C4 C 0.290(3) 0.747(2) 0.217(2) 0.076(6) Uani 1 1 d . . .
H4 H 0.2954 0.8156 0.1449 0.092 Uiso 1 1 calc R . .
C2 C 0.154(3) 0.666(2) 0.410(2) 0.078(7) Uani 1 1 d . . .
H2 H 0.0672 0.6791 0.4714 0.094 Uiso 1 1 calc R . .
N2 N 0.7061(19) 0.3921(13) 0.2792(11) 0.041(4) Uani 1 1 d . . .
N1 N 0.280(2) 0.3638(16) 0.2675(18) 0.058(4) Uani 1 1 d . . .
N3 N 1.034(2) 0.0894(14) 0.3366(12) 0.040(4) Uani 1 1 d . . .
O1 O 0.133(2) 0.3492(17) 0.3344(15) 0.096(5) Uani 1 1 d . . .
O2 O 0.281(2) 0.4320(15) 0.1660(15) 0.089(5) Uani 1 1 d . . .
O3 O 0.7802(15) 0.1187(10) 0.4711(9) 0.051(3) Uani 1 1 d . . .
H6 H 0.795(19) 0.398(12) 0.307(10) 0.02(4) Uiso 1 1 d . . .
H10 H 1.08(3) 0.01(2) 0.38(2) 0.10(9) 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
C10 0.037(10) 0.026(9) 0.036(9) -0.014(8) -0.017(8) 0.012(7)
C7 0.056(12) 0.033(10) 0.039(10) -0.013(8) -0.012(9) -0.013(8)
C18 0.036(9) 0.027(10) 0.041(10) -0.013(9) -0.010(8) -0.003(7)
C15 0.054(12) 0.037(10) 0.047(12) -0.020(9) -0.011(9) -0.008(9)
C13 0.052(12) 0.043(11) 0.038(10) -0.010(9) 0.007(10) -0.022(10)
C16 0.045(11) 0.036(10) 0.034(11) -0.014(8) -0.008(9) -0.002(9)
C8 0.034(10) 0.038(10) 0.049(10) -0.010(8) -0.006(8) -0.018(8)
C12 0.046(11) 0.037(10) 0.035(10) -0.008(9) -0.010(9) -0.007(8)
C17 0.046(12) 0.026(9) 0.035(11) -0.011(8) -0.002(9) -0.012(9)
C9 0.041(10) 0.041(10) 0.035(9) -0.011(8) -0.013(8) 0.001(8)
C11 0.029(9) 0.032(9) 0.040(11) -0.011(8) -0.004(8) -0.006(8)
C23 0.057(12) 0.054(12) 0.051(12) -0.025(9) 0.002(9) -0.026(9)
C21 0.076(14) 0.043(12) 0.082(16) -0.033(12) -0.010(12) -0.008(11)
C14 0.053(12) 0.061(13) 0.048(13) -0.028(11) 0.006(10) -0.018(11)
C19 0.060(12) 0.042(12) 0.043(11) -0.015(9) -0.004(9) -0.011(9)
C22 0.050(12) 0.070(14) 0.074(14) -0.048(12) 0.013(10) -0.020(10)
C5 0.066(13) 0.037(12) 0.067(14) -0.022(11) 0.010(10) 0.002(10)
C3 0.057(14) 0.055(14) 0.12(2) -0.039(16) -0.022(14) 0.008(11)
C6 0.037(10) 0.040(11) 0.054(12) -0.022(10) -0.006(9) -0.012(8)
C20 0.078(14) 0.040(12) 0.056(13) -0.008(10) -0.014(11) -0.016(10)
C1 0.068(14) 0.076(15) 0.053(13) -0.025(11) -0.006(11) -0.014(12)
C4 0.053(13) 0.061(15) 0.091(17) -0.018(12) -0.009(13) 0.003(11)
C2 0.059(14) 0.082(17) 0.096(19) -0.064(16) 0.007(12) 0.011(13)
N2 0.028(8) 0.046(9) 0.042(8) -0.014(7) -0.008(7) -0.002(7)
N1 0.036(10) 0.066(11) 0.091(14) -0.045(11) -0.013(10) -0.011(8)
N3 0.053(11) 0.027(8) 0.035(9) -0.008(8) -0.008(7) -0.007(8)
O1 0.043(9) 0.142(15) 0.133(14) -0.087(12) 0.002(9) -0.021(9)
O2 0.096(12) 0.079(11) 0.084(11) -0.024(9) -0.048(10) 0.004(9)
O3 0.054(7) 0.045(7) 0.030(7) -0.005(5) -0.004(6) 0.002(6)
_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
C10 N2 1.466(19) . ?
C10 C11 1.49(2) . ?
C10 C9 1.54(2) . ?
C10 C17 1.55(2) . ?
C7 N2 1.45(2) . ?
C7 C6 1.53(2) . ?
C7 C8 1.54(2) . ?
C7 H7 0.9800 . ?
C18 C19 1.36(2) . ?
C18 C23 1.40(2) . ?
C18 C9 1.51(2) . ?
C15 C16 1.35(2) . ?
C15 C14 1.39(2) . ?
C15 H15 0.9300 . ?
C13 C14 1.37(2) . ?
C13 C12 1.38(2) . ?
C13 H13 0.9300 . ?
C16 C11 1.40(2) . ?
C16 N3 1.42(2) . ?
C8 N1 1.51(2) . ?
C8 C9 1.52(2) . ?
C8 H8 0.9800 . ?
C12 C11 1.38(2) . ?
C12 H12 0.9300 . ?
C17 O3 1.235(18) . ?
C17 N3 1.34(2) . ?
C9 H9 0.9800 . ?
C23 C22 1.39(2) . ?
C23 H23 0.9300 . ?
C21 C20 1.36(3) . ?
C21 C22 1.37(3) . ?
C21 H21 0.9300 . ?
C14 H14 0.9300 . ?
C19 C20 1.39(2) . ?
C19 H19 0.9300 . ?
C22 H22 0.9300 . ?
C5 C4 1.37(3) . ?
C5 C6 1.37(2) . ?
C5 H5 0.9300 . ?
C3 C2 1.36(3) . ?
C3 C4 1.36(3) . ?
C3 H3 0.9300 . ?
C6 C1 1.38(2) . ?
C20 H20 0.9300 . ?
C1 C2 1.40(3) . ?
C1 H1 0.9300 . ?
C4 H4 0.9300 . ?
C2 H2 0.9300 . ?
N2 H6 0.87(14) . ?
N1 O2 1.20(2) . ?
N1 O1 1.249(19) . ?
N3 H10 0.8(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
N2 C10 C11 116.4(13) . . ?
N2 C10 C9 100.4(12) . . ?
C11 C10 C9 113.1(12) . . ?
N2 C10 C17 115.0(12) . . ?
C11 C10 C17 101.7(12) . . ?
C9 C10 C17 110.8(12) . . ?
N2 C7 C6 112.9(12) . . ?
N2 C7 C8 103.2(12) . . ?
C6 C7 C8 116.8(13) . . ?
N2 C7 H7 107.8 . . ?
C6 C7 H7 107.8 . . ?
C8 C7 H7 107.8 . . ?
C19 C18 C23 117.5(14) . . ?
C19 C18 C9 124.6(14) . . ?
C23 C18 C9 117.8(14) . . ?
C16 C15 C14 117.7(16) . . ?
C16 C15 H15 121.2 . . ?
C14 C15 H15 121.2 . . ?
C14 C13 C12 120.4(15) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C16 C11 122.3(14) . . ?
C15 C16 N3 129.7(15) . . ?
C11 C16 N3 108.0(14) . . ?
N1 C8 C9 111.5(13) . . ?
N1 C8 C7 112.2(12) . . ?
C9 C8 C7 106.5(12) . . ?
N1 C8 H8 108.9 . . ?
C9 C8 H8 108.9 . . ?
C7 C8 H8 108.9 . . ?
C11 C12 C13 119.0(15) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
O3 C17 N3 127.4(14) . . ?
O3 C17 C10 124.7(14) . . ?
N3 C17 C10 107.9(14) . . ?
C18 C9 C8 119.3(13) . . ?
C18 C9 C10 114.4(12) . . ?
C8 C9 C10 102.5(12) . . ?
C18 C9 H9 106.6 . . ?
C8 C9 H9 106.6 . . ?
C10 C9 H9 106.6 . . ?
C12 C11 C16 119.2(14) . . ?
C12 C11 C10 130.8(14) . . ?
C16 C11 C10 110.0(13) . . ?
C22 C23 C18 120.8(16) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
C20 C21 C22 120.7(17) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C13 C14 C15 121.3(16) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C18 C19 C20 122.4(16) . . ?
C18 C19 H19 118.8 . . ?
C20 C19 H19 118.8 . . ?
C21 C22 C23 119.6(17) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C4 C5 C6 120.8(18) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C2 C3 C4 119.9(19) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C6 C1 118.3(16) . . ?
C5 C6 C7 121.2(15) . . ?
C1 C6 C7 120.5(16) . . ?
C21 C20 C19 118.9(17) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C6 C1 C2 120.6(19) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C4 C5 121(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C3 C2 C1 119.5(19) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C7 N2 C10 108.2(12) . . ?
C7 N2 H6 118(8) . . ?
C10 N2 H6 102(8) . . ?
O2 N1 O1 122.7(17) . . ?
O2 N1 C8 120.2(16) . . ?
O1 N1 C8 117.0(17) . . ?
C17 N3 C16 112.3(14) . . ?
C17 N3 H10 117(10) . . ?
C16 N3 H10 128(10) . . ?
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
C14 C15 C16 C11 4(2) . . . . ?
C14 C15 C16 N3 -179.6(15) . . . . ?
N2 C7 C8 N1 -118.4(14) . . . . ?
C6 C7 C8 N1 6(2) . . . . ?
N2 C7 C8 C9 3.9(15) . . . . ?
C6 C7 C8 C9 128.4(14) . . . . ?
C14 C13 C12 C11 1(2) . . . . ?
N2 C10 C17 O3 50(2) . . . . ?
C11 C10 C17 O3 177.0(14) . . . . ?
C9 C10 C17 O3 -62.5(18) . . . . ?
N2 C10 C17 N3 -131.4(14) . . . . ?
C11 C10 C17 N3 -4.8(15) . . . . ?
C9 C10 C17 N3 115.7(14) . . . . ?
C19 C18 C9 C8 -27(2) . . . . ?
C23 C18 C9 C8 157.3(14) . . . . ?
C19 C18 C9 C10 95.0(18) . . . . ?
C23 C18 C9 C10 -80.9(17) . . . . ?
N1 C8 C9 C18 -88.0(16) . . . . ?
C7 C8 C9 C18 149.3(13) . . . . ?
N1 C8 C9 C10 144.6(12) . . . . ?
C7 C8 C9 C10 21.9(15) . . . . ?
N2 C10 C9 C18 -169.6(12) . . . . ?
C11 C10 C9 C18 65.8(17) . . . . ?
C17 C10 C9 C18 -47.6(17) . . . . ?
N2 C10 C9 C8 -39.0(14) . . . . ?
C11 C10 C9 C8 -163.7(12) . . . . ?
C17 C10 C9 C8 82.9(14) . . . . ?
C13 C12 C11 C16 1(2) . . . . ?
C13 C12 C11 C10 -175.7(15) . . . . ?
C15 C16 C11 C12 -4(2) . . . . ?
N3 C16 C11 C12 179.4(13) . . . . ?
C15 C16 C11 C10 173.7(14) . . . . ?
N3 C16 C11 C10 -3.3(17) . . . . ?
N2 C10 C11 C12 -53(2) . . . . ?
C9 C10 C11 C12 63(2) . . . . ?
C17 C10 C11 C12 -178.3(15) . . . . ?
N2 C10 C11 C16 130.5(14) . . . . ?
C9 C10 C11 C16 -114.0(14) . . . . ?
C17 C10 C11 C16 4.8(16) . . . . ?
C19 C18 C23 C22 1(2) . . . . ?
C9 C18 C23 C22 177.0(15) . . . . ?
C12 C13 C14 C15 0(2) . . . . ?
C16 C15 C14 C13 -2(2) . . . . ?
C23 C18 C19 C20 -3(2) . . . . ?
C9 C18 C19 C20 -179.1(15) . . . . ?
C20 C21 C22 C23 0(3) . . . . ?
C18 C23 C22 C21 1(3) . . . . ?
C4 C5 C6 C1 -1(3) . . . . ?
C4 C5 C6 C7 178.4(17) . . . . ?
N2 C7 C6 C5 31(2) . . . . ?
C8 C7 C6 C5 -88.5(19) . . . . ?
N2 C7 C6 C1 -149.4(16) . . . . ?
C8 C7 C6 C1 91.2(19) . . . . ?
C22 C21 C20 C19 -2(3) . . . . ?
C18 C19 C20 C21 4(3) . . . . ?
C5 C6 C1 C2 1(3) . . . . ?
C7 C6 C1 C2 -178.3(17) . . . . ?
C2 C3 C4 C5 -1(3) . . . . ?
C6 C5 C4 C3 1(3) . . . . ?
C4 C3 C2 C1 1(3) . . . . ?
C6 C1 C2 C3 -1(3) . . . . ?
C6 C7 N2 C10 -157.5(12) . . . . ?
C8 C7 N2 C10 -30.5(15) . . . . ?
C11 C10 N2 C7 166.7(12) . . . . ?
C9 C10 N2 C7 44.3(14) . . . . ?
C17 C10 N2 C7 -74.6(16) . . . . ?
C9 C8 N1 O2 -38(2) . . . . ?
C7 C8 N1 O2 81.7(19) . . . . ?
C9 C8 N1 O1 144.7(15) . . . . ?
C7 C8 N1 O1 -96.0(17) . . . . ?
O3 C17 N3 C16 -178.7(15) . . . . ?
C10 C17 N3 C16 3.1(17) . . . . ?
C15 C16 N3 C17 -176.7(16) . . . . ?
C11 C16 N3 C17 0.0(18) . . . . ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 19.98
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.654
_refine_diff_density_min -0.691
_refine_diff_density_rms 0.182