# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2012
data_global
_journal_name_full 'RSC Advances'
_journal_coden_cambridge 1500
_journal_year ?
_journal_volume ?
_journal_page_first ?
loop_
_publ_author_address
;
FIRST AUTHORS ADDRESS
;
_publ_contact_author
;
Madeleine Helliwell
;
_publ_contact_author_email TJSnape@uclan.ac.uk
_publ_contact_author_fax ' ENTER FAX NUMBER '
_publ_contact_author_phone ' ENTER PHONE NUMBER '
_publ_contact_letter
;
ENTER TEXT OF LETTER
;
_publ_requested_coeditor_name ?
_publ_section_title
;
ENTER SECTION TITLE
;
_publ_contact_author_address
;
Department of Chemistry
University of Manchester
Manchester M13 9PL
England UK
;
#TrackingRef '- s3173o.cif'
#------------------ SUBMISSION DETAILS --------------------------------------#
# Name and address of author for correspondence
_publ_contact_author_name 'Tim Snape'
_publ_requested_category ?
loop_
_publ_author_name
T.J.Snape
S.Ward
# Attachment '- s3173o.cif'
data_s3173o
_database_code_depnum_ccdc_archive 'CCDC 744673'
_publ_section_title_footnote
;
?
;
#------------------ TEXT ----------------------------------------------------#
_publ_section_synopsis
;
# Insert blank lines between paragraphs
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;
_publ_section_abstract
;
# Insert blank lines between paragraphs
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_publ_section_comment
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# Insert blank lines between paragraphs
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_publ_section_exptl_prep
;
?
;
_publ_section_exptl_refinement
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The structure was solved by direct methods.
The non-hydrogen atoms were refined anisotropically. H atoms were included in
calculated positions with C-H lengths of 0.95(CH), 0.99(CH~2~) &
0.98(CH~3~)\%A; U\~iso(H) values were fixed at 1.2U~eq~(C) except for CH~3~
where it was 1.5U~eq~(C).
;
# Insert blank lines between references
_publ_section_references
;
#
# Put all your general crystallographic references here
# Delete as required from the document CIF
#
Bruker (2000). GEMINI (Version 1.02) and RLATT (Version 3.0).
Bruker AXS In=c., Madison, Wisconsin, USA.
Bruker (2001) SMART (Version 5.625), SADABS (Version 2.03a) and
SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2003). SMART (Version 5.630) and SAINT-Plus (Version 6.45A).
Bruker AXS Inc., Madison, Wisconsin, USA.
M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini,
G. L. Cascarano, L. De Caro,C. Giacovazzo, G. Polidori
and R. Spagna
SIR2004: an improved tool for crystal structure determination
and refinement
J. Appl. Cryst. (2005). 38, 381-388
Sheldrick, G.M. (1993) SHELXL93. Program for crystal structure
refinement. University of G\"ottingen, Germany.
Sheldrick, G.M. (1997) SHELXL97. Program for crystal structure
refinement. University of G\"ottingen, Germany.
Sheldrick, G.M. (1985). SHELXS86. In Crystallographic Computing 3,
edited by G. M. Sheldrick, C. Kruger & R. Goddard, pp. 175-189.
Oxford University Press.
Sheldrick, G.M. (1997) SHELXS97. Program for Crystal Structure solution.
University of G\"ottingen, Germany.
Sheldrick, G, M. (2005). CELL_NOW. University
of G\"ottingen, Germany.
Sheldrick, G, M. (2007). TWINABS. University
of G\"ottingen, Germany.
Sheldrick, G. M. (2008) A short history of SHELX . Acta Cryst. A64, 112-122.
Wilson, A.J.C. (1992) Ed. International Tables for Crystallography,
Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;
_publ_section_figure_captions
;
Figure 1. View of (I) (50% probability displacement ellipsoids)
;
_publ_section_acknowledgements
;
?
;
_publ_section_table_legends
;
Table 1. Fractional atomic coordinates and equivalent
isotropic displacement parameters (\%A^2^)
Table 2. Selected geometric parameters (\%A ,\% )
;
#------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------#
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C18 H22 N2 O5'
_chemical_formula_weight 346.38
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'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M P2(1)/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 11.1965(17)
_cell_length_b 15.030(2)
_cell_length_c 10.6135(16)
_cell_angle_alpha 90.00
_cell_angle_beta 106.835(3)
_cell_angle_gamma 90.00
_cell_volume 1709.6(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 1232
_cell_measurement_theta_min 2.691
_cell_measurement_theta_max 23.285
_exptl_crystal_description plate
_exptl_crystal_colour white
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.05
_exptl_crystal_density_diffrn 1.346
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 736
_exptl_absorpt_coefficient_mu 0.099
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 10421
_diffrn_reflns_av_R_equivalents 0.0726
_diffrn_reflns_av_sigmaI/netI 0.0787
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_theta_min 1.90
_diffrn_reflns_theta_max 23.25
_reflns_number_total 2462
_reflns_number_gt 1975
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker SMART'
_computing_cell_refinement 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_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^)+(0.0350P)^2^+0.7456P] 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 2462
_refine_ls_number_parameters 231
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0980
_refine_ls_R_factor_gt 0.0740
_refine_ls_wR_factor_ref 0.1329
_refine_ls_wR_factor_gt 0.1243
_refine_ls_goodness_of_fit_ref 1.202
_refine_ls_restrained_S_all 1.202
_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 0.4790(2) 0.17766(16) 0.4608(2) 0.0145(6) Uani 1 1 d . . .
O2 O 0.4280(2) 0.06083(16) 0.2636(2) 0.0156(6) Uani 1 1 d . . .
O3 O 0.5978(2) 0.02401(17) 0.1348(2) 0.0187(7) Uani 1 1 d . . .
O4 O 0.9070(2) 0.29075(17) 0.5992(3) 0.0175(7) Uani 1 1 d . . .
O5 O 1.2515(2) 0.37303(17) 0.0770(3) 0.0186(7) Uani 1 1 d . . .
N1 N 0.8829(3) 0.2400(2) 0.3902(3) 0.0159(8) Uani 1 1 d . . .
H1 H 0.9201 0.2373 0.3277 0.019 Uiso 1 1 calc R . .
N2 N 1.0345(3) 0.3432(2) 0.4858(3) 0.0194(8) Uani 1 1 d . . .
C1 C 0.7708(3) 0.1913(2) 0.3696(4) 0.0132(9) Uani 1 1 d . . .
C2 C 0.7460(4) 0.1277(2) 0.2702(4) 0.0144(9) Uani 1 1 d . . .
H2 H 0.8066 0.1147 0.2260 0.017 Uiso 1 1 calc R . .
C3 C 0.6334(3) 0.0835(3) 0.2360(4) 0.0148(9) Uani 1 1 d . . .
C4 C 0.5449(3) 0.1004(2) 0.3025(4) 0.0122(9) Uani 1 1 d . . .
C5 C 0.5717(3) 0.1628(3) 0.4030(4) 0.0157(9) Uani 1 1 d . . .
C6 C 0.6840(3) 0.2097(3) 0.4366(4) 0.0143(9) Uani 1 1 d . . .
H6 H 0.7007 0.2535 0.5040 0.017 Uiso 1 1 calc R . .
C7 C 0.5019(4) 0.2434(3) 0.5627(4) 0.0192(10) Uani 1 1 d . . .
H7A H 0.5127 0.3017 0.5262 0.029 Uiso 1 1 calc R . .
H7B H 0.5777 0.2278 0.6326 0.029 Uiso 1 1 calc R . .
H7C H 0.4310 0.2456 0.5992 0.029 Uiso 1 1 calc R . .
C8 C 0.4302(4) -0.0317(3) 0.2991(4) 0.0223(10) Uani 1 1 d . . .
H8A H 0.4818 -0.0648 0.2548 0.033 Uiso 1 1 calc R . .
H8B H 0.3450 -0.0554 0.2721 0.033 Uiso 1 1 calc R . .
H8C H 0.4653 -0.0378 0.3946 0.033 Uiso 1 1 calc R . .
C9 C 0.6793(3) 0.0141(3) 0.0530(4) 0.0178(10) Uani 1 1 d . . .
H9A H 0.6924 0.0723 0.0174 0.027 Uiso 1 1 calc R . .
H9B H 0.6414 -0.0267 -0.0196 0.027 Uiso 1 1 calc R . .
H9C H 0.7596 -0.0100 0.1056 0.027 Uiso 1 1 calc R . .
C10 C 0.9391(3) 0.2908(3) 0.4980(4) 0.0146(9) Uani 1 1 d . . .
C11 C 1.1061(4) 0.3952(3) 0.5984(4) 0.0257(11) Uani 1 1 d . . .
H11A H 1.0709 0.3869 0.6721 0.039 Uiso 1 1 calc R . .
H11B H 1.1023 0.4583 0.5745 0.039 Uiso 1 1 calc R . .
H11C H 1.1932 0.3753 0.6245 0.039 Uiso 1 1 calc R . .
C12 C 1.0796(4) 0.3452(3) 0.3712(4) 0.0158(9) Uani 1 1 d . . .
C13 C 1.1880(4) 0.3001(3) 0.3742(4) 0.0186(10) Uani 1 1 d . . .
H13 H 1.2256 0.2621 0.4463 0.022 Uiso 1 1 calc R . .
C14 C 1.2423(4) 0.3097(3) 0.2730(4) 0.0200(10) Uani 1 1 d . . .
H14 H 1.3167 0.2785 0.2754 0.024 Uiso 1 1 calc R . .
C15 C 1.1873(3) 0.3649(3) 0.1689(4) 0.0150(9) Uani 1 1 d . . .
C16 C 1.0761(3) 0.4074(3) 0.1613(4) 0.0161(9) Uani 1 1 d . . .
H16 H 1.0363 0.4432 0.0872 0.019 Uiso 1 1 calc R . .
C17 C 1.0231(4) 0.3969(3) 0.2643(4) 0.0182(10) Uani 1 1 d . . .
H17 H 0.9467 0.4261 0.2603 0.022 Uiso 1 1 calc R . .
C18 C 1.2044(4) 0.4328(3) -0.0313(4) 0.0213(10) Uani 1 1 d . . .
H18A H 1.1200 0.4147 -0.0814 0.032 Uiso 1 1 calc R . .
H18B H 1.2590 0.4312 -0.0887 0.032 Uiso 1 1 calc R . .
H18C H 1.2022 0.4934 0.0022 0.032 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 0.0147(14) 0.0171(15) 0.0141(15) -0.0058(12) 0.0079(12) -0.0011(12)
O2 0.0140(15) 0.0137(15) 0.0194(16) -0.0020(12) 0.0054(12) -0.0057(12)
O3 0.0188(16) 0.0243(16) 0.0161(15) -0.0086(13) 0.0100(12) -0.0047(13)
O4 0.0146(15) 0.0266(17) 0.0139(16) -0.0014(13) 0.0083(12) -0.0024(13)
O5 0.0217(16) 0.0226(16) 0.0156(16) 0.0009(13) 0.0118(13) 0.0029(13)
N1 0.0175(19) 0.021(2) 0.0133(19) -0.0054(15) 0.0106(15) -0.0042(16)
N2 0.0201(19) 0.028(2) 0.0127(19) -0.0044(16) 0.0084(15) -0.0130(17)
C1 0.011(2) 0.012(2) 0.017(2) 0.0013(18) 0.0059(17) -0.0011(18)
C2 0.017(2) 0.013(2) 0.015(2) 0.0074(18) 0.0081(18) 0.0030(18)
C3 0.016(2) 0.017(2) 0.010(2) 0.0054(18) 0.0020(17) 0.0028(18)
C4 0.014(2) 0.012(2) 0.009(2) 0.0023(17) 0.0026(17) 0.0017(17)
C5 0.014(2) 0.021(2) 0.013(2) 0.0094(19) 0.0054(18) 0.0062(19)
C6 0.015(2) 0.015(2) 0.013(2) -0.0010(17) 0.0032(18) 0.0012(18)
C7 0.018(2) 0.020(2) 0.023(3) -0.0098(19) 0.0107(19) -0.0050(19)
C8 0.028(3) 0.017(2) 0.023(2) -0.001(2) 0.009(2) -0.009(2)
C9 0.016(2) 0.022(2) 0.016(2) -0.0053(19) 0.0059(18) 0.0025(19)
C10 0.012(2) 0.018(2) 0.016(2) 0.0022(19) 0.0083(19) 0.0022(18)
C11 0.028(3) 0.032(3) 0.019(2) -0.012(2) 0.011(2) -0.012(2)
C12 0.017(2) 0.021(2) 0.010(2) -0.0038(19) 0.0047(17) -0.0077(19)
C13 0.021(2) 0.015(2) 0.016(2) 0.0062(18) 0.0001(19) -0.0009(19)
C14 0.020(2) 0.021(2) 0.019(2) 0.001(2) 0.0063(19) 0.000(2)
C15 0.014(2) 0.017(2) 0.016(2) -0.0024(18) 0.0079(18) -0.0046(18)
C16 0.019(2) 0.020(2) 0.009(2) 0.0017(18) 0.0032(18) 0.0016(19)
C17 0.013(2) 0.021(2) 0.020(2) -0.005(2) 0.0063(19) 0.0005(19)
C18 0.029(3) 0.021(2) 0.018(2) 0.008(2) 0.012(2) 0.004(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 C5 1.368(4) . ?
O1 C7 1.433(4) . ?
O2 C4 1.388(4) . ?
O2 C8 1.439(4) . ?
O3 C3 1.365(4) . ?
O3 C9 1.437(4) . ?
O4 C10 1.227(4) . ?
O5 C15 1.374(4) . ?
O5 C18 1.434(4) . ?
N1 C10 1.368(5) . ?
N1 C1 1.414(5) . ?
N1 H1 0.8800 . ?
N2 C10 1.364(5) . ?
N2 C12 1.446(5) . ?
N2 C11 1.459(5) . ?
C1 C6 1.388(5) . ?
C1 C2 1.391(5) . ?
C2 C3 1.378(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(5) . ?
C4 C5 1.387(5) . ?
C5 C6 1.394(5) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.369(5) . ?
C12 C13 1.382(5) . ?
C13 C14 1.387(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(5) . ?
C16 C17 1.396(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C5 O1 C7 117.2(3) . . ?
C4 O2 C8 113.2(3) . . ?
C3 O3 C9 116.8(3) . . ?
C15 O5 C18 118.6(3) . . ?
C10 N1 C1 126.2(3) . . ?
C10 N1 H1 116.9 . . ?
C1 N1 H1 116.9 . . ?
C10 N2 C12 124.5(3) . . ?
C10 N2 C11 119.4(3) . . ?
C12 N2 C11 115.8(3) . . ?
C6 C1 C2 120.7(4) . . ?
C6 C1 N1 122.7(3) . . ?
C2 C1 N1 116.5(3) . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
O3 C3 C2 124.0(3) . . ?
O3 C3 C4 115.4(3) . . ?
C2 C3 C4 120.6(4) . . ?
O2 C4 C5 119.6(3) . . ?
O2 C4 C3 121.2(3) . . ?
C5 C4 C3 119.0(3) . . ?
O1 C5 C4 115.6(3) . . ?
O1 C5 C6 123.2(4) . . ?
C4 C5 C6 121.1(4) . . ?
C1 C6 C5 118.8(4) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
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 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 N2 121.3(4) . . ?
O4 C10 N1 123.5(3) . . ?
N2 C10 N1 115.2(3) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 119.3(4) . . ?
C17 C12 N2 121.2(4) . . ?
C13 C12 N2 119.3(3) . . ?
C12 C13 C14 120.7(4) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.3(4) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
O5 C15 C14 114.8(3) . . ?
O5 C15 C16 124.4(3) . . ?
C14 C15 C16 120.8(4) . . ?
C15 C16 C17 118.8(4) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C12 C17 C16 120.9(4) . . ?
C12 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C10 N1 C1 C6 20.2(6) . . . . ?
C10 N1 C1 C2 -164.9(4) . . . . ?
C6 C1 C2 C3 1.1(6) . . . . ?
N1 C1 C2 C3 -173.9(3) . . . . ?
C9 O3 C3 C2 -5.9(5) . . . . ?
C9 O3 C3 C4 171.7(3) . . . . ?
C1 C2 C3 O3 175.9(3) . . . . ?
C1 C2 C3 C4 -1.5(5) . . . . ?
C8 O2 C4 C5 -110.0(4) . . . . ?
C8 O2 C4 C3 74.6(4) . . . . ?
O3 C3 C4 O2 -2.0(5) . . . . ?
C2 C3 C4 O2 175.7(3) . . . . ?
O3 C3 C4 C5 -177.3(3) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C7 O1 C5 C4 -178.4(3) . . . . ?
C7 O1 C5 C6 -1.6(5) . . . . ?
O2 C4 C5 O1 2.7(5) . . . . ?
C3 C4 C5 O1 178.1(3) . . . . ?
O2 C4 C5 C6 -174.2(3) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
C2 C1 C6 C5 0.5(6) . . . . ?
N1 C1 C6 C5 175.2(3) . . . . ?
O1 C5 C6 C1 -178.3(3) . . . . ?
C4 C5 C6 C1 -1.7(5) . . . . ?
C12 N2 C10 O4 178.3(4) . . . . ?
C11 N2 C10 O4 4.7(6) . . . . ?
C12 N2 C10 N1 -2.1(5) . . . . ?
C11 N2 C10 N1 -175.7(3) . . . . ?
C1 N1 C10 O4 10.2(6) . . . . ?
C1 N1 C10 N2 -169.3(3) . . . . ?
C10 N2 C12 C17 84.0(5) . . . . ?
C11 N2 C12 C17 -102.2(4) . . . . ?
C10 N2 C12 C13 -101.6(4) . . . . ?
C11 N2 C12 C13 72.3(5) . . . . ?
C17 C12 C13 C14 2.7(6) . . . . ?
N2 C12 C13 C14 -171.8(3) . . . . ?
C12 C13 C14 C15 0.1(6) . . . . ?
C18 O5 C15 C14 -176.8(3) . . . . ?
C18 O5 C15 C16 3.4(5) . . . . ?
C13 C14 C15 O5 177.1(3) . . . . ?
C13 C14 C15 C16 -3.1(6) . . . . ?
O5 C15 C16 C17 -177.1(3) . . . . ?
C14 C15 C16 C17 3.1(6) . . . . ?
C13 C12 C17 C16 -2.6(6) . . . . ?
N2 C12 C17 C16 171.8(3) . . . . ?
C15 C16 C17 C12 -0.2(6) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O4 0.88 2.42 3.211(4) 149.0 4_565
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 23.25
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.234
_refine_diff_density_min -0.245
_refine_diff_density_rms 0.055
data_s3171m
_database_code_depnum_ccdc_archive 'CCDC 744677'
#TrackingRef '- s3171m.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_publ_section_abstract
;
ENTER ABSTRACT
;
_publ_section_exptl_prep
;
ENTER EXPERIMENTAL SECTION
;
_publ_section_exptl_refinement
;
The structure was solved by the direct methods
and there are two molecules in the asymmetric unit.
All non-H atoms were refined anisotropically.
H atoms were included in calculated positions.
;
_publ_section_comment
;
ENTER TEXT
;
_publ_section_references
;
Bruker (2001). SMART (Version 5.625), SADABS (Version 2.03a) and
SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2002). SAINT. Version 6.36a. Bruker AXS Inc., Madison,
Wisconsin, USA.
M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini,
G. L. Cascarano, L. De Caro,C. Giacovazzo, G. Polidori
and R. Spagna
SIR2004: an improved tool for crystal structure determination
and refinement
J. Appl. Cryst. (2005). 38, 381-388
Sheldrick, G. M. (1997). SHELXS-97 and SHELXL-97.
University of G\"ottingen, Germany.
Sheldrick, G, M. (2005). CELL_NOW. University
of G\"ottingen, Germany.
Sheldrick, G, M. (2007). TWINABS. University
of G\"ottingen, Germany.
Spek, A.L. (2003) J.Appl.Cryst. 36, 2003, 7-13.
;
_publ_section_acknowledgements
;
ENTER ACKNOWLEDGEMENTS
;
_publ_section_table_legends
;
ENTER TABLE LEGENDS
;
_publ_section_figure_captions
;
ENTER FIGURE CAPTIONS
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C19 H24 N2 O5'
_chemical_formula_weight 360.40
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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 9.868(4)
_cell_length_b 13.348(6)
_cell_length_c 15.424(7)
_cell_angle_alpha 66.326(7)
_cell_angle_beta 86.745(8)
_cell_angle_gamma 76.657(7)
_cell_volume 1808.8(13)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 859
_cell_measurement_theta_min 2.405
_cell_measurement_theta_max 25.865
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.15
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.323
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 768
_exptl_absorpt_coefficient_mu 0.096
_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 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 12863
_diffrn_reflns_av_R_equivalents 0.1107
_diffrn_reflns_av_sigmaI/netI 0.1250
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_theta_min 1.71
_diffrn_reflns_theta_max 25.03
_reflns_number_total 6314
_reflns_number_gt 4104
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker SMART'
_computing_cell_refinement 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_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^)+(0.0707P)^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 6314
_refine_ls_number_parameters 481
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1117
_refine_ls_R_factor_gt 0.0709
_refine_ls_wR_factor_ref 0.1810
_refine_ls_wR_factor_gt 0.1643
_refine_ls_goodness_of_fit_ref 1.043
_refine_ls_restrained_S_all 1.043
_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 0.1078(3) 0.88633(18) 0.09497(16) 0.0258(6) Uani 1 1 d . . .
O2 O -0.0146(3) 1.04964(18) 0.15288(17) 0.0257(6) Uani 1 1 d . . .
O3 O 0.0763(3) 1.05501(17) 0.31002(16) 0.0236(6) Uani 1 1 d . . .
O4 O 0.4696(3) 0.60683(18) 0.53815(16) 0.0259(6) Uani 1 1 d . . .
O5 O -0.1301(3) 0.6449(2) 0.23239(18) 0.0310(6) Uani 1 1 d . . .
N1 N 0.4063(3) 0.6976(2) 0.38059(19) 0.0209(7) Uani 1 1 d . . .
N2 N 0.2439(3) 0.6346(2) 0.49488(19) 0.0228(7) Uani 1 1 d . . .
C1 C 0.3030(4) 0.7903(3) 0.3195(2) 0.0194(8) Uani 1 1 d . . .
C2 C 0.2626(4) 0.7909(3) 0.2347(2) 0.0196(8) Uani 1 1 d . . .
H2 H 0.3058 0.7318 0.2159 0.024 Uiso 1 1 calc R . .
C3 C 0.1586(4) 0.8786(3) 0.1778(2) 0.0213(8) Uani 1 1 d . . .
C4 C 0.0945(4) 0.9648(3) 0.2065(2) 0.0201(8) Uani 1 1 d . . .
C5 C 0.1417(4) 0.9651(3) 0.2886(2) 0.0192(8) Uani 1 1 d . . .
C6 C 0.2461(4) 0.8787(3) 0.3459(2) 0.0202(8) Uani 1 1 d . . .
H6 H 0.2782 0.8797 0.4024 0.024 Uiso 1 1 calc R . .
C7 C 0.1531(4) 0.7907(3) 0.0713(3) 0.0295(9) Uani 1 1 d . . .
H7A H 0.2526 0.7810 0.0586 0.044 Uiso 1 1 calc R . .
H7B H 0.1002 0.8024 0.0148 0.044 Uiso 1 1 calc R . .
H7C H 0.1373 0.7234 0.1243 0.044 Uiso 1 1 calc R . .
C8 C -0.1377(4) 1.0114(3) 0.1546(3) 0.0343(10) Uani 1 1 d . . .
H8A H -0.1227 0.9596 0.1226 0.051 Uiso 1 1 calc R . .
H8B H -0.2145 1.0757 0.1219 0.051 Uiso 1 1 calc R . .
H8C H -0.1612 0.9724 0.2204 0.051 Uiso 1 1 calc R . .
C9 C 0.1137(4) 1.0501(3) 0.3994(2) 0.0248(8) Uani 1 1 d . . .
H9A H 0.0936 0.9824 0.4497 0.037 Uiso 1 1 calc R . .
H9B H 0.0598 1.1167 0.4081 0.037 Uiso 1 1 calc R . .
H9C H 0.2134 1.0477 0.4020 0.037 Uiso 1 1 calc R . .
C10 C 0.5489(4) 0.7081(3) 0.3597(3) 0.0264(9) Uani 1 1 d . . .
H10A H 0.5672 0.7676 0.3761 0.040 Uiso 1 1 calc R . .
H10B H 0.5629 0.7269 0.2920 0.040 Uiso 1 1 calc R . .
H10C H 0.6131 0.6367 0.3969 0.040 Uiso 1 1 calc R . .
C11 C 0.3782(4) 0.6439(2) 0.4755(2) 0.0193(8) Uani 1 1 d . . .
C12 C 0.2057(4) 0.5989(3) 0.5935(2) 0.0294(9) Uani 1 1 d . . .
H12A H 0.2368 0.5171 0.6257 0.044 Uiso 1 1 calc R . .
H12B H 0.1043 0.6209 0.5965 0.044 Uiso 1 1 calc R . .
H12C H 0.2505 0.6347 0.6247 0.044 Uiso 1 1 calc R . .
C13 C 0.1480(4) 0.6319(3) 0.4296(2) 0.0216(8) Uani 1 1 d . . .
C14 C 0.1827(4) 0.5545(3) 0.3885(2) 0.0230(8) Uani 1 1 d . . .
H14 H 0.2686 0.5001 0.4059 0.028 Uiso 1 1 calc R . .
C15 C 0.0923(4) 0.5563(3) 0.3224(2) 0.0248(8) Uani 1 1 d . . .
H15 H 0.1171 0.5043 0.2932 0.030 Uiso 1 1 calc R . .
C16 C -0.0347(4) 0.6340(3) 0.2985(2) 0.0238(8) Uani 1 1 d . . .
C17 C -0.0714(4) 0.7074(3) 0.3439(2) 0.0240(8) Uani 1 1 d . . .
H17 H -0.1602 0.7579 0.3306 0.029 Uiso 1 1 calc R . .
C18 C 0.0196(4) 0.7071(3) 0.4073(2) 0.0246(8) Uani 1 1 d . . .
H18 H -0.0054 0.7590 0.4364 0.030 Uiso 1 1 calc R . .
C19 C -0.0903(4) 0.5809(3) 0.1759(3) 0.0348(10) Uani 1 1 d . . .
H19A H -0.0031 0.5959 0.1452 0.052 Uiso 1 1 calc R . .
H19B H -0.1637 0.6023 0.1274 0.052 Uiso 1 1 calc R . .
H19C H -0.0767 0.5007 0.2164 0.052 Uiso 1 1 calc R . .
O6 O 0.1055(3) 0.38945(18) 0.09247(16) 0.0244(6) Uani 1 1 d . . .
O7 O 0.2329(3) 0.56096(17) 0.03887(16) 0.0236(6) Uani 1 1 d . . .
O8 O 0.4256(3) 0.56596(17) 0.15072(16) 0.0238(6) Uani 1 1 d . . .
O9 O 0.5689(3) 0.10839(19) 0.49185(17) 0.0287(6) Uani 1 1 d . . .
O10 O 0.3990(3) 0.1643(2) -0.00209(18) 0.0367(7) Uani 1 1 d . . .
N3 N 0.3823(3) 0.2011(2) 0.38789(19) 0.0221(7) Uani 1 1 d . . .
N4 N 0.6022(3) 0.1418(2) 0.3368(2) 0.0239(7) Uani 1 1 d . . .
C20 C 0.3413(4) 0.2950(3) 0.2988(2) 0.0202(8) Uani 1 1 d . . .
C21 C 0.2407(4) 0.2930(3) 0.2417(2) 0.0224(8) Uani 1 1 d . . .
H21 H 0.1975 0.2312 0.2616 0.027 Uiso 1 1 calc R . .
C22 C 0.2031(4) 0.3824(3) 0.1547(2) 0.0202(8) Uani 1 1 d . . .
C23 C 0.2687(4) 0.4720(3) 0.1259(2) 0.0203(8) Uani 1 1 d . . .
C24 C 0.3674(4) 0.4735(3) 0.1853(2) 0.0205(8) Uani 1 1 d . . .
C25 C 0.4038(4) 0.3855(3) 0.2730(2) 0.0218(8) Uani 1 1 d . . .
H25 H 0.4701 0.3871 0.3144 0.026 Uiso 1 1 calc R . .
C26 C 0.0548(4) 0.2911(3) 0.1113(3) 0.0304(9) Uani 1 1 d . . .
H26A H 0.1337 0.2273 0.1208 0.046 Uiso 1 1 calc R . .
H26B H -0.0045 0.3033 0.0575 0.046 Uiso 1 1 calc R . .
H26C H 0.0005 0.2752 0.1685 0.046 Uiso 1 1 calc R . .
C27 C 0.2860(4) 0.5315(3) -0.0381(2) 0.0286(9) Uani 1 1 d . . .
H27A H 0.3873 0.5229 -0.0389 0.043 Uiso 1 1 calc R . .
H27B H 0.2433 0.5909 -0.0980 0.043 Uiso 1 1 calc R . .
H27C H 0.2636 0.4606 -0.0302 0.043 Uiso 1 1 calc R . .
C28 C 0.5366(4) 0.5647(3) 0.2063(3) 0.0261(9) Uani 1 1 d . . .
H28A H 0.5048 0.5552 0.2699 0.039 Uiso 1 1 calc R . .
H28B H 0.5664 0.6357 0.1764 0.039 Uiso 1 1 calc R . .
H28C H 0.6151 0.5023 0.2109 0.039 Uiso 1 1 calc R . .
C29 C 0.2964(4) 0.2089(3) 0.4665(2) 0.0265(8) Uani 1 1 d . . .
H29A H 0.3168 0.1363 0.5210 0.040 Uiso 1 1 calc R . .
H29B H 0.1976 0.2288 0.4470 0.040 Uiso 1 1 calc R . .
H29C H 0.3171 0.2667 0.4842 0.040 Uiso 1 1 calc R . .
C30 C 0.5202(4) 0.1483(3) 0.4100(3) 0.0234(8) Uani 1 1 d . . .
C31 C 0.7518(4) 0.1055(3) 0.3541(3) 0.0350(10) Uani 1 1 d . . .
H31A H 0.7798 0.1341 0.3981 0.053 Uiso 1 1 calc R . .
H31B H 0.7982 0.1347 0.2942 0.053 Uiso 1 1 calc R . .
H31C H 0.7788 0.0233 0.3817 0.053 Uiso 1 1 calc R . .
C32 C 0.5485(4) 0.1427(3) 0.2517(2) 0.0219(8) Uani 1 1 d . . .
C33 C 0.4820(4) 0.0618(3) 0.2532(2) 0.0234(8) Uani 1 1 d . . .
H33 H 0.4717 0.0029 0.3119 0.028 Uiso 1 1 calc R . .
C34 C 0.4304(4) 0.0651(3) 0.1705(3) 0.0263(9) Uani 1 1 d . . .
H34 H 0.3832 0.0098 0.1724 0.032 Uiso 1 1 calc R . .
C35 C 0.4479(4) 0.1503(3) 0.0843(3) 0.0258(8) Uani 1 1 d . . .
C36 C 0.5171(4) 0.2303(3) 0.0818(3) 0.0253(8) Uani 1 1 d . . .
H36 H 0.5296 0.2881 0.0230 0.030 Uiso 1 1 calc R . .
C37 C 0.5680(4) 0.2261(3) 0.1648(2) 0.0236(8) Uani 1 1 d . . .
H37 H 0.6169 0.2805 0.1628 0.028 Uiso 1 1 calc R . .
C38 C 0.3166(5) 0.0901(4) -0.0045(3) 0.0449(11) Uani 1 1 d . . .
H38A H 0.3706 0.0123 0.0245 0.067 Uiso 1 1 calc R . .
H38B H 0.2909 0.1081 -0.0705 0.067 Uiso 1 1 calc R . .
H38C H 0.2320 0.0991 0.0306 0.067 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 0.0402(16) 0.0179(12) 0.0175(13) -0.0088(10) -0.0064(11) 0.0018(11)
O2 0.0327(15) 0.0142(12) 0.0257(14) -0.0061(10) -0.0107(11) 0.0022(11)
O3 0.0357(15) 0.0132(12) 0.0200(13) -0.0071(10) -0.0056(11) 0.0003(11)
O4 0.0335(15) 0.0170(12) 0.0228(14) -0.0045(11) -0.0109(12) -0.0011(11)
O5 0.0330(16) 0.0318(14) 0.0294(15) -0.0140(12) -0.0049(12) -0.0049(12)
N1 0.0239(17) 0.0152(14) 0.0195(15) -0.0049(12) -0.0034(13) 0.0003(12)
N2 0.0324(19) 0.0179(15) 0.0134(15) -0.0016(12) -0.0033(13) -0.0049(13)
C1 0.025(2) 0.0150(16) 0.0171(18) -0.0035(14) -0.0026(15) -0.0061(15)
C2 0.024(2) 0.0119(16) 0.0198(18) -0.0035(14) 0.0027(15) -0.0041(15)
C3 0.028(2) 0.0167(17) 0.0181(18) -0.0046(15) -0.0033(16) -0.0073(15)
C4 0.024(2) 0.0130(16) 0.0191(18) -0.0022(14) -0.0025(15) -0.0036(15)
C5 0.025(2) 0.0122(16) 0.0198(18) -0.0064(14) 0.0017(15) -0.0043(15)
C6 0.027(2) 0.0144(17) 0.0167(18) -0.0029(14) -0.0039(15) -0.0052(15)
C7 0.044(3) 0.0215(19) 0.022(2) -0.0105(16) -0.0049(18) -0.0015(18)
C8 0.031(2) 0.025(2) 0.043(2) -0.0117(18) -0.0149(19) 0.0033(17)
C9 0.031(2) 0.0208(18) 0.0231(19) -0.0118(16) -0.0018(16) -0.0008(16)
C10 0.030(2) 0.0221(19) 0.026(2) -0.0105(16) -0.0086(17) -0.0005(16)
C11 0.032(2) 0.0071(15) 0.0194(18) -0.0068(14) -0.0053(17) -0.0010(15)
C12 0.044(3) 0.0220(19) 0.0188(19) -0.0058(16) 0.0023(17) -0.0049(18)
C13 0.032(2) 0.0152(17) 0.0143(17) -0.0008(14) -0.0002(16) -0.0081(16)
C14 0.029(2) 0.0135(17) 0.0213(19) -0.0030(15) -0.0023(16) -0.0011(15)
C15 0.035(2) 0.0190(18) 0.0232(19) -0.0085(15) 0.0033(17) -0.0110(17)
C16 0.026(2) 0.0222(19) 0.0225(19) -0.0063(16) -0.0011(16) -0.0077(16)
C17 0.021(2) 0.0196(18) 0.026(2) -0.0042(16) 0.0020(16) -0.0043(15)
C18 0.032(2) 0.0170(17) 0.027(2) -0.0100(16) 0.0065(17) -0.0087(16)
C19 0.040(3) 0.042(2) 0.029(2) -0.0201(19) -0.0030(19) -0.010(2)
O6 0.0334(15) 0.0163(12) 0.0200(13) -0.0025(10) -0.0109(11) -0.0050(11)
O7 0.0352(15) 0.0120(11) 0.0176(13) -0.0022(10) -0.0069(11) 0.0012(11)
O8 0.0333(15) 0.0131(12) 0.0235(13) -0.0044(10) -0.0056(11) -0.0059(11)
O9 0.0399(16) 0.0202(13) 0.0213(14) -0.0040(11) -0.0140(12) -0.0022(12)
O10 0.0551(19) 0.0338(15) 0.0247(15) -0.0110(12) -0.0007(13) -0.0179(14)
N3 0.0314(18) 0.0171(14) 0.0145(15) -0.0023(12) -0.0047(13) -0.0050(13)
N4 0.0238(17) 0.0196(15) 0.0234(16) -0.0036(13) -0.0063(14) -0.0029(13)
C20 0.025(2) 0.0158(17) 0.0178(18) -0.0061(14) -0.0018(15) -0.0009(15)
C21 0.026(2) 0.0152(17) 0.0241(19) -0.0069(15) -0.0011(16) -0.0021(15)
C22 0.0203(19) 0.0176(17) 0.0229(19) -0.0106(15) -0.0010(16) 0.0007(15)
C23 0.029(2) 0.0121(16) 0.0162(17) -0.0041(14) -0.0019(15) 0.0011(15)
C24 0.025(2) 0.0123(16) 0.0239(19) -0.0081(15) -0.0001(16) -0.0019(15)
C25 0.026(2) 0.0177(17) 0.0217(18) -0.0091(15) -0.0061(16) -0.0003(15)
C26 0.035(2) 0.0225(19) 0.036(2) -0.0119(17) -0.0063(19) -0.0090(17)
C27 0.042(2) 0.0210(19) 0.0209(19) -0.0056(16) -0.0016(17) -0.0073(18)
C28 0.034(2) 0.0166(18) 0.030(2) -0.0109(16) -0.0033(17) -0.0065(16)
C29 0.033(2) 0.0249(19) 0.0212(19) -0.0085(16) -0.0002(17) -0.0072(17)
C30 0.028(2) 0.0128(17) 0.028(2) -0.0062(16) -0.0064(17) -0.0052(15)
C31 0.040(3) 0.025(2) 0.033(2) -0.0029(18) -0.0070(19) -0.0075(19)
C32 0.022(2) 0.0142(17) 0.0245(19) -0.0047(15) -0.0028(16) 0.0012(15)
C33 0.027(2) 0.0129(17) 0.0224(19) -0.0002(15) -0.0012(16) -0.0011(15)
C34 0.032(2) 0.0205(18) 0.029(2) -0.0112(16) 0.0010(17) -0.0080(16)
C35 0.027(2) 0.0243(19) 0.025(2) -0.0112(16) -0.0032(16) 0.0000(16)
C36 0.028(2) 0.0168(17) 0.025(2) -0.0042(15) 0.0015(16) -0.0013(16)
C37 0.023(2) 0.0130(17) 0.029(2) -0.0044(15) 0.0016(16) -0.0002(15)
C38 0.058(3) 0.048(3) 0.038(3) -0.019(2) -0.003(2) -0.023(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 C3 1.356(4) . ?
O1 C7 1.433(4) . ?
O2 C4 1.382(4) . ?
O2 C8 1.418(4) . ?
O3 C5 1.380(4) . ?
O3 C9 1.419(4) . ?
O4 C11 1.225(4) . ?
O5 C16 1.368(4) . ?
O5 C19 1.431(4) . ?
N1 C11 1.392(4) . ?
N1 C1 1.431(4) . ?
N1 C10 1.452(5) . ?
N2 C11 1.365(5) . ?
N2 C13 1.436(4) . ?
N2 C12 1.455(4) . ?
C1 C2 1.386(5) . ?
C1 C6 1.388(5) . ?
C2 C3 1.385(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(5) . ?
C4 C5 1.376(5) . ?
C5 C6 1.381(4) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.385(5) . ?
C13 C14 1.388(5) . ?
C14 C15 1.382(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(5) . ?
C17 C18 1.362(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O6 C22 1.359(4) . ?
O6 C26 1.427(4) . ?
O7 C23 1.385(4) . ?
O7 C27 1.430(4) . ?
O8 C24 1.378(4) . ?
O8 C28 1.422(4) . ?
O9 C30 1.232(4) . ?
O10 C35 1.370(4) . ?
O10 C38 1.430(4) . ?
N3 C30 1.372(4) . ?
N3 C20 1.438(4) . ?
N3 C29 1.464(4) . ?
N4 C30 1.371(5) . ?
N4 C32 1.437(4) . ?
N4 C31 1.449(5) . ?
C20 C21 1.376(5) . ?
C20 C25 1.389(4) . ?
C21 C22 1.390(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.394(4) . ?
C23 C24 1.384(5) . ?
C24 C25 1.386(5) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.380(5) . ?
C32 C37 1.394(5) . ?
C33 C34 1.380(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.393(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.382(5) . ?
C36 C37 1.376(5) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 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
C3 O1 C7 117.1(3) . . ?
C4 O2 C8 112.6(2) . . ?
C5 O3 C9 116.1(3) . . ?
C16 O5 C19 117.9(3) . . ?
C11 N1 C1 119.0(3) . . ?
C11 N1 C10 116.7(3) . . ?
C1 N1 C10 114.4(3) . . ?
C11 N2 C13 124.2(3) . . ?
C11 N2 C12 117.4(3) . . ?
C13 N2 C12 116.7(3) . . ?
C2 C1 C6 121.2(3) . . ?
C2 C1 N1 119.5(3) . . ?
C6 C1 N1 119.3(3) . . ?
C1 C2 C3 119.2(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
O1 C3 C2 124.4(3) . . ?
O1 C3 C4 115.4(3) . . ?
C2 C3 C4 120.1(3) . . ?
C5 C4 O2 119.9(3) . . ?
C5 C4 C3 119.3(3) . . ?
O2 C4 C3 120.8(3) . . ?
C4 C5 O3 115.7(3) . . ?
C4 C5 C6 121.2(3) . . ?
O3 C5 C6 123.1(3) . . ?
C5 C6 C1 118.8(3) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
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 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 N2 122.0(3) . . ?
O4 C11 N1 121.6(3) . . ?
N2 C11 N1 116.5(3) . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 119.4(3) . . ?
C18 C13 N2 119.9(3) . . ?
C14 C13 N2 120.7(3) . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
O5 C16 C15 124.9(3) . . ?
O5 C16 C17 115.9(3) . . ?
C15 C16 C17 119.2(3) . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 120.7(3) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 O6 C26 117.3(3) . . ?
C23 O7 C27 112.2(2) . . ?
C24 O8 C28 116.8(2) . . ?
C35 O10 C38 118.1(3) . . ?
C30 N3 C20 120.4(3) . . ?
C30 N3 C29 116.4(3) . . ?
C20 N3 C29 114.0(3) . . ?
C30 N4 C32 123.3(3) . . ?
C30 N4 C31 118.3(3) . . ?
C32 N4 C31 116.7(3) . . ?
C21 C20 C25 121.7(3) . . ?
C21 C20 N3 119.1(3) . . ?
C25 C20 N3 119.1(3) . . ?
C20 C21 C22 119.3(3) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
O6 C22 C21 124.4(3) . . ?
O6 C22 C23 115.8(3) . . ?
C21 C22 C23 119.7(3) . . ?
C24 C23 O7 119.8(3) . . ?
C24 C23 C22 120.0(3) . . ?
O7 C23 C22 120.1(3) . . ?
O8 C24 C23 115.6(3) . . ?
O8 C24 C25 123.8(3) . . ?
C23 C24 C25 120.5(3) . . ?
C20 C25 C24 118.6(3) . . ?
C20 C25 H25 120.7 . . ?
C24 C25 H25 120.7 . . ?
O6 C26 H26A 109.5 . . ?
O6 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O6 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O7 C27 H27A 109.5 . . ?
O7 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O7 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O8 C28 H28A 109.5 . . ?
O8 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O8 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C29 H29A 109.5 . . ?
N3 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N3 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O9 C30 N3 121.9(3) . . ?
O9 C30 N4 121.2(3) . . ?
N3 C30 N4 117.0(3) . . ?
N4 C31 H31A 109.5 . . ?
N4 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N4 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 C37 119.0(3) . . ?
C33 C32 N4 122.0(3) . . ?
C37 C32 N4 118.9(3) . . ?
C32 C33 C34 120.9(3) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 H33 119.6 . . ?
C33 C34 C35 119.5(3) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 H34 120.3 . . ?
O10 C35 C36 114.8(3) . . ?
O10 C35 C34 125.1(3) . . ?
C36 C35 C34 120.1(3) . . ?
C37 C36 C35 119.8(3) . . ?
C37 C36 H36 120.1 . . ?
C35 C36 H36 120.1 . . ?
C36 C37 C32 120.6(3) . . ?
C36 C37 H37 119.7 . . ?
C32 C37 H37 119.7 . . ?
O10 C38 H38A 109.5 . . ?
O10 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O10 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 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
C11 N1 C1 C2 -128.6(3) . . . . ?
C10 N1 C1 C2 86.8(4) . . . . ?
C11 N1 C1 C6 52.0(4) . . . . ?
C10 N1 C1 C6 -92.6(4) . . . . ?
C6 C1 C2 C3 -3.2(5) . . . . ?
N1 C1 C2 C3 177.4(3) . . . . ?
C7 O1 C3 C2 8.0(5) . . . . ?
C7 O1 C3 C4 -169.4(3) . . . . ?
C1 C2 C3 O1 -178.0(3) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C8 O2 C4 C5 -111.2(4) . . . . ?
C8 O2 C4 C3 69.4(4) . . . . ?
O1 C3 C4 C5 -178.4(3) . . . . ?
C2 C3 C4 C5 4.0(5) . . . . ?
O1 C3 C4 O2 1.0(5) . . . . ?
C2 C3 C4 O2 -176.5(3) . . . . ?
O2 C4 C5 O3 -1.7(5) . . . . ?
C3 C4 C5 O3 177.8(3) . . . . ?
O2 C4 C5 C6 176.9(3) . . . . ?
C3 C4 C5 C6 -3.6(5) . . . . ?
C9 O3 C5 C4 173.5(3) . . . . ?
C9 O3 C5 C6 -5.2(5) . . . . ?
C4 C5 C6 C1 -0.2(5) . . . . ?
O3 C5 C6 C1 178.3(3) . . . . ?
C2 C1 C6 C5 3.7(5) . . . . ?
N1 C1 C6 C5 -176.9(3) . . . . ?
C13 N2 C11 O4 -153.1(3) . . . . ?
C12 N2 C11 O4 11.7(4) . . . . ?
C13 N2 C11 N1 26.8(4) . . . . ?
C12 N2 C11 N1 -168.4(3) . . . . ?
C1 N1 C11 O4 -144.2(3) . . . . ?
C10 N1 C11 O4 -0.4(4) . . . . ?
C1 N1 C11 N2 36.0(4) . . . . ?
C10 N1 C11 N2 179.8(3) . . . . ?
C11 N2 C13 C18 -125.9(4) . . . . ?
C12 N2 C13 C18 69.2(4) . . . . ?
C11 N2 C13 C14 54.1(4) . . . . ?
C12 N2 C13 C14 -110.8(4) . . . . ?
C18 C13 C14 C15 3.1(5) . . . . ?
N2 C13 C14 C15 -176.9(3) . . . . ?
C13 C14 C15 C16 -1.4(5) . . . . ?
C19 O5 C16 C15 -7.5(5) . . . . ?
C19 O5 C16 C17 172.7(3) . . . . ?
C14 C15 C16 O5 178.3(3) . . . . ?
C14 C15 C16 C17 -1.9(5) . . . . ?
O5 C16 C17 C18 -176.6(3) . . . . ?
C15 C16 C17 C18 3.6(5) . . . . ?
C16 C17 C18 C13 -1.9(5) . . . . ?
C14 C13 C18 C17 -1.5(5) . . . . ?
N2 C13 C18 C17 178.5(3) . . . . ?
C30 N3 C20 C21 127.1(4) . . . . ?
C29 N3 C20 C21 -87.3(4) . . . . ?
C30 N3 C20 C25 -53.2(4) . . . . ?
C29 N3 C20 C25 92.4(4) . . . . ?
C25 C20 C21 C22 1.8(5) . . . . ?
N3 C20 C21 C22 -178.5(3) . . . . ?
C26 O6 C22 C21 -10.3(5) . . . . ?
C26 O6 C22 C23 168.9(3) . . . . ?
C20 C21 C22 O6 179.9(3) . . . . ?
C20 C21 C22 C23 0.8(5) . . . . ?
C27 O7 C23 C24 108.1(4) . . . . ?
C27 O7 C23 C22 -73.5(4) . . . . ?
O6 C22 C23 C24 178.6(3) . . . . ?
C21 C22 C23 C24 -2.2(5) . . . . ?
O6 C22 C23 O7 0.2(5) . . . . ?
C21 C22 C23 O7 179.4(3) . . . . ?
C28 O8 C24 C23 -174.2(3) . . . . ?
C28 O8 C24 C25 5.0(5) . . . . ?
O7 C23 C24 O8 -1.2(5) . . . . ?
C22 C23 C24 O8 -179.6(3) . . . . ?
O7 C23 C24 C25 179.6(3) . . . . ?
C22 C23 C24 C25 1.1(5) . . . . ?
C21 C20 C25 C24 -2.8(5) . . . . ?
N3 C20 C25 C24 177.5(3) . . . . ?
O8 C24 C25 C20 -177.9(3) . . . . ?
C23 C24 C25 C20 1.3(5) . . . . ?
C20 N3 C30 O9 145.7(3) . . . . ?
C29 N3 C30 O9 0.8(4) . . . . ?
C20 N3 C30 N4 -34.4(4) . . . . ?
C29 N3 C30 N4 -179.2(3) . . . . ?
C32 N4 C30 O9 153.6(3) . . . . ?
C31 N4 C30 O9 -11.2(5) . . . . ?
C32 N4 C30 N3 -26.4(4) . . . . ?
C31 N4 C30 N3 168.9(3) . . . . ?
C30 N4 C32 C33 -60.2(4) . . . . ?
C31 N4 C32 C33 104.8(4) . . . . ?
C30 N4 C32 C37 121.8(4) . . . . ?
C31 N4 C32 C37 -73.2(4) . . . . ?
C37 C32 C33 C34 -2.5(5) . . . . ?
N4 C32 C33 C34 179.4(3) . . . . ?
C32 C33 C34 C35 1.2(5) . . . . ?
C38 O10 C35 C36 -175.1(3) . . . . ?
C38 O10 C35 C34 3.7(5) . . . . ?
C33 C34 C35 O10 -178.5(3) . . . . ?
C33 C34 C35 C36 0.3(5) . . . . ?
O10 C35 C36 C37 178.5(3) . . . . ?
C34 C35 C36 C37 -0.4(5) . . . . ?
C35 C36 C37 C32 -1.0(5) . . . . ?
C33 C32 C37 C36 2.5(5) . . . . ?
N4 C32 C37 C36 -179.4(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full 25.03
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max 0.345
_refine_diff_density_min -0.297
_refine_diff_density_rms 0.066