# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010
data_global
_journal_coden_Cambridge 182
loop_
_publ_author_name
_publ_author_address
'Hani Hassan'
;
?
;
'Fraser K. Brown' ''
_publ_contact_author_name 'Hani Hassan'
_publ_contact_author_email H.HASSAN@SHEFFIELD.AC.UK
_publ_section_title
;
A Convenient Approach to Acyclic Unsaturated
Amino Acids via Ring-Closing Metathesis.
;
_publ_requested_coeditor_name ?
_publ_contact_author
;
;
_publ_contact_author_fax ?
_publ_contact_author_phone ?
_publ_contact_letter
;
?
;
#------------------------------------------------------------------------------
_publ_requested_journal ?
# Attachment 'Supporting_Information_for_Publication__compound_6a_.cif.txt'
data_CRYSTALS_cif
_database_code_depnum_ccdc_archive 'CCDC 766489'
#TrackingRef 'Supporting_Information_for_Publication__compound_6a_.cif.txt'
_oxford_structure_analysis_title ?
_chemical_name_systematic ?
_chemical_melting_point ?
_cell_length_a 9.8608(2)
_cell_length_b 9.8608(2)
_cell_length_c 24.3886(12)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 2371.43(14)
_symmetry_cell_setting Tetragonal
_symmetry_space_group_name_H-M 'P 43 '
_symmetry_space_group_name_Hall ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-y,x,z+3/4
-x,-y,z+1/2
y,-x,z+1/4
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 4
# Given Formula = C25 H8.50 N2.50 O7.50
# Dc = 1.30 Fooo = 912.00 Mu = 0.99 M = 463.85
# Found Formula = C22 H34 N2 O6
# Dc = 1.18 FOOO = 912.00 Mu = 0.86 M = 422.52
_chemical_formula_sum 'C22 H34 N2 O6'
_chemical_formula_moiety 'C22 H34 N2 O6'
_chemical_compound_source ?
_chemical_formula_weight 422.52
_cell_measurement_reflns_used 1989
_cell_measurement_theta_min 6
_cell_measurement_theta_max 43
_cell_measurement_temperature 150
_exptl_crystal_description colourless
_exptl_crystal_colour block
_exptl_crystal_size_min 0.23
_exptl_crystal_size_mid 0.24
_exptl_crystal_size_max 0.76
_exptl_crystal_density_diffrn 1.183
_exptl_crystal_density_meas ?
# Non-dispersive F(000):
_exptl_crystal_F_000 912
_exptl_absorpt_coefficient_mu 0.086
# Sheldrick geometric approximatio 0.98 0.98
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min 0.84
_exptl_absorpt_correction_T_max 0.98
_diffrn_measurement_device_type 'Bruker SMART'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_method \w
_computing_data_collection 'SMART (Siemens, 1993)'
_computing_data_reduction 'SAINT (Siemens ,1995)'
_computing_cell_refinement 'SAINT (Siemens ,1995)'
_computing_structure_solution 'SIR92 (Altomare et al, 1994)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al 2003)'
_computing_publication_material 'CRYSTALS (Betteridge et al 2003)'
_computing_molecular_graphics 'CAMERON (Watkin et al 1996)'
_diffrn_standards_interval_time ?
_diffrn_standards_interval_count ?
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 150
_diffrn_reflns_number 13598
_reflns_number_total 3665
_diffrn_reflns_av_R_equivalents 0.035
# Number of reflections with Friedels Law is 3665
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 3610
_diffrn_reflns_theta_min 2.065
_diffrn_reflns_theta_max 30.478
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full 29.869
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 34
_reflns_limit_h_min -9
_reflns_limit_h_max 9
_reflns_limit_k_min 0
_reflns_limit_k_max 14
_reflns_limit_l_min 0
_reflns_limit_l_max 34
_oxford_diffrn_Wilson_B_factor 3.02
_oxford_diffrn_Wilson_scale 5.46
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.38
_refine_diff_density_max 0.41
_refine_ls_number_reflns 3655
_refine_ls_number_restraints 253
_refine_ls_number_parameters 271
#_refine_ls_R_factor_ref 0.0926
_refine_ls_wR_factor_ref 0.0865
_refine_ls_goodness_of_fit_ref 0.9639
#_reflns_number_all 3655
_refine_ls_R_factor_all 0.0926
_refine_ls_wR_factor_all 0.0865
# No actual I/u(I) cutoff was used for refinement. The
# threshold below is used for "_gt" information ONLY:
_reflns_threshold_expression I>2.00u(I)
_reflns_number_gt 2050
_refine_ls_R_factor_gt 0.0529
_refine_ls_wR_factor_gt 0.0681
_refine_ls_shift/su_max 0.000205
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration unk
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment noref # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
6.58 7.14 1.73
;
_publ_section_exptl_refinement
;H atoms placed geometrically after each cycle
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C.,
Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution
of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.
Siemens Industrial Automation, Inc (1993)
SMART: Area-Detector Software Package; Madison, WI.
Siemens Industrial Automation, Inc (1995).
SAINT: Area-Detector Integration Software.; Madison, WI.
Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.
Watkin D.J. (1994),
Acta Cryst, A50, 411-437
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical
Crystallography Laboratory, OXFORD, UK.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.4713(3) 0.1057(3) 0.64252(11) 0.0475 1.0000 Uani . U . . . .
C2 C 0.3709(4) 0.0502(3) 0.66017(15) 0.0357 1.0000 Uani . U . . . .
C3 C 0.3670(4) -0.0062(3) 0.71753(15) 0.0411 1.0000 Uani . U . . . .
C4 C 0.4722(4) 0.0632(4) 0.75377(16) 0.0465 1.0000 Uani . U . . . .
C5 C 0.4420(4) 0.2095(4) 0.76285(17) 0.0457 1.0000 Uani . U . . . .
C6 C 0.4032(4) 0.2665(4) 0.80847(17) 0.0474 1.0000 Uani . U . . . .
C7 C 0.3629(4) 0.4115(4) 0.81688(16) 0.0415 1.0000 Uani . U . . . .
N8 N 0.3666(3) 0.4915(3) 0.76600(13) 0.0397 1.0000 Uani . U . . . .
C9 C 0.4861(4) 0.5622(4) 0.75132(16) 0.0411 1.0000 Uani . U . . . .
O10 O 0.5845(2) 0.5267(3) 0.78421(11) 0.0472 1.0000 Uani . U . . . .
C11 C 0.7265(4) 0.5685(4) 0.7732(2) 0.0519 1.0000 Uani . U . . . .
C12 C 0.7415(5) 0.7194(5) 0.7773(2) 0.0700 1.0000 Uani . U . . . .
C13 C 0.8011(5) 0.5007(5) 0.8190(3) 0.0762 1.0000 Uani . U . . . .
O15 O 0.4910(3) 0.6464(3) 0.71554(13) 0.0604 1.0000 Uani . U . . . .
O16 O 0.1492(3) 0.4340(3) 0.75112(11) 0.0531 1.0000 Uani . U . . . .
C17 C 0.2508(4) 0.4871(4) 0.73269(16) 0.0402 1.0000 Uani . U . . . .
C18 C 0.2555(4) 0.5408(4) 0.67500(17) 0.0444 1.0000 Uani . U . . . .
C19 C 0.1524(4) 0.4703(4) 0.63858(18) 0.0515 1.0000 Uani . U . . . .
C20 C 0.1821(4) 0.3253(4) 0.63038(17) 0.0461 1.0000 Uani . U . . . .
C21 C 0.2198(4) 0.2677(4) 0.58402(16) 0.0431 1.0000 Uani . U . . . .
C22 C 0.2609(4) 0.1230(4) 0.57551(15) 0.0408 1.0000 Uani . U . . . .
N23 N 0.2557(3) 0.0422(3) 0.62618(12) 0.0372 1.0000 Uani . U . . . .
C24 C 0.1384(4) -0.0305(4) 0.63958(17) 0.0394 1.0000 Uani . U . . . .
O25 O 0.0405(2) 0.0043(3) 0.60534(12) 0.0480 1.0000 Uani . U . . . .
C26 C -0.0971(4) -0.0558(4) 0.6083(2) 0.0629 1.0000 Uani . U . . . .
C27 C -0.1672(5) 0.0146(5) 0.5615(3) 0.0887 1.0000 Uani . U . . . .
C28 C -0.1594(5) -0.0197(7) 0.6616(3) 0.0995 1.0000 Uani . U . . . .
C29 C -0.0861(5) -0.2079(5) 0.5998(3) 0.0914 1.0000 Uani . U . . . .
O30 O 0.1313(3) -0.1134(3) 0.67585(13) 0.0567 1.0000 Uani . U . . . .
C14 C 0.7660(5) 0.5127(7) 0.7187(2) 0.0999 1.0000 Uani . U . . . .
H31 H 0.2748 0.0089 0.7334 0.0488 1.0000 Uiso . . . . . .
H32 H 0.3867 -0.1056 0.7163 0.0488 1.0000 Uiso . . . . . .
H41 H 0.4739 0.0166 0.7902 0.0549 1.0000 Uiso . . . . . .
H42 H 0.5629 0.0551 0.7359 0.0549 1.0000 Uiso . . . . . .
H51 H 0.4531 0.2709 0.7303 0.0538 1.0000 Uiso . . . . . .
H61 H 0.4000 0.2065 0.8415 0.0561 1.0000 Uiso . . . . . .
H71 H 0.4264 0.4535 0.8440 0.0491 1.0000 Uiso . . . . . .
H72 H 0.2685 0.4139 0.8319 0.0491 1.0000 Uiso . . . . . .
H121 H 0.8379 0.7451 0.7701 0.0824 1.0000 Uiso . . . . . .
H122 H 0.7161 0.7491 0.8154 0.0824 1.0000 Uiso . . . . . .
H123 H 0.6808 0.7642 0.7503 0.0824 1.0000 Uiso . . . . . .
H131 H 0.9001 0.5213 0.8161 0.0907 1.0000 Uiso . . . . . .
H132 H 0.7659 0.5347 0.8550 0.0907 1.0000 Uiso . . . . . .
H133 H 0.7871 0.4003 0.8168 0.0907 1.0000 Uiso . . . . . .
H181 H 0.2357 0.6403 0.6756 0.0524 1.0000 Uiso . . . . . .
H182 H 0.3483 0.5254 0.6596 0.0524 1.0000 Uiso . . . . . .
H191 H 0.0607 0.4794 0.6558 0.0610 1.0000 Uiso . . . . . .
H192 H 0.1519 0.5163 0.6019 0.0610 1.0000 Uiso . . . . . .
H201 H 0.1728 0.2649 0.6632 0.0548 1.0000 Uiso . . . . . .
H211 H 0.2213 0.3272 0.5508 0.0513 1.0000 Uiso . . . . . .
H221 H 0.3556 0.1211 0.5609 0.0484 1.0000 Uiso . . . . . .
H222 H 0.1980 0.0812 0.5480 0.0484 1.0000 Uiso . . . . . .
H271 H -0.2629 -0.0181 0.5587 0.1056 1.0000 Uiso . . . . . .
H272 H -0.1663 0.1146 0.5677 0.1056 1.0000 Uiso . . . . . .
H273 H -0.1184 -0.0064 0.5263 0.1056 1.0000 Uiso . . . . . .
H281 H -0.2521 -0.0601 0.6640 0.1192 1.0000 Uiso . . . . . .
H282 H -0.1020 -0.0556 0.6922 0.1192 1.0000 Uiso . . . . . .
H283 H -0.1659 0.0812 0.6647 0.1192 1.0000 Uiso . . . . . .
H291 H -0.1783 -0.2493 0.6016 0.1084 1.0000 Uiso . . . . . .
H292 H -0.0270 -0.2479 0.6288 0.1084 1.0000 Uiso . . . . . .
H293 H -0.0452 -0.2263 0.5628 0.1084 1.0000 Uiso . . . . . .
H141 H 0.8616 0.5395 0.7103 0.1180 1.0000 Uiso . . . . . .
H142 H 0.7586 0.4118 0.7194 0.1180 1.0000 Uiso . . . . . .
H143 H 0.7042 0.5502 0.6899 0.1180 1.0000 Uiso . . . . . .
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 0.0401(14) 0.0591(17) 0.0432(15) 0.0025(13) 0.0026(12) -0.0092(12)
C2 0.0382(15) 0.0322(17) 0.0366(15) -0.0015(14) 0.0048(12) 0.0026(13)
C3 0.051(2) 0.0305(17) 0.0420(17) 0.0060(14) 0.0009(15) 0.0013(15)
C4 0.052(2) 0.0451(17) 0.042(2) 0.0095(16) -0.0036(17) -0.0007(16)
C5 0.045(2) 0.0451(17) 0.047(2) 0.0026(16) -0.0018(18) -0.0020(16)
C6 0.052(2) 0.0478(18) 0.043(2) 0.0058(16) -0.0003(18) -0.0006(18)
C7 0.0391(19) 0.0489(18) 0.0364(17) -0.0024(14) 0.0012(16) -0.0018(16)
N8 0.0383(14) 0.0396(16) 0.0412(16) -0.0017(12) 0.0014(12) -0.0007(12)
C9 0.0374(16) 0.0389(19) 0.047(2) -0.0022(14) 0.0008(14) -0.0017(14)
O10 0.0354(12) 0.0464(15) 0.0598(18) 0.0060(13) -0.0031(11) -0.0037(11)
C11 0.0303(15) 0.0502(19) 0.075(2) -0.005(2) 0.0010(17) -0.0026(16)
C12 0.050(3) 0.0512(19) 0.109(4) 0.009(2) -0.014(3) -0.0120(19)
C13 0.051(3) 0.055(3) 0.122(4) 0.016(3) -0.025(3) -0.006(2)
O15 0.0499(17) 0.0607(19) 0.070(2) 0.0211(15) -0.0075(15) -0.0112(14)
O16 0.0409(15) 0.0654(19) 0.0530(18) -0.0143(15) 0.0044(13) -0.0115(13)
C17 0.0377(16) 0.0370(19) 0.0459(17) -0.0092(15) 0.0001(13) 0.0008(14)
C18 0.046(2) 0.0355(19) 0.0518(19) 0.0001(16) -0.0068(16) 0.0055(15)
C19 0.052(2) 0.0500(19) 0.052(2) 0.0002(18) -0.0081(19) 0.0006(18)
C20 0.052(2) 0.0461(18) 0.0406(19) 0.0028(15) -0.0092(17) -0.0008(17)
C21 0.0388(19) 0.0471(17) 0.0434(19) 0.0117(15) 0.0046(16) 0.0024(16)
C22 0.040(2) 0.0470(17) 0.0352(17) 0.0028(14) 0.0009(15) -0.0036(15)
N23 0.0380(14) 0.0353(15) 0.0383(16) 0.0016(12) 0.0012(12) -0.0043(12)
C24 0.0377(16) 0.0295(17) 0.051(2) 0.0007(14) 0.0031(14) 0.0007(13)
O25 0.0374(13) 0.0423(14) 0.0644(18) 0.0072(13) -0.0059(12) -0.0071(11)
C26 0.0323(18) 0.050(2) 0.106(3) 0.016(2) -0.001(2) -0.0051(17)
C27 0.048(3) 0.077(3) 0.141(4) 0.031(4) -0.033(3) -0.014(2)
C28 0.052(3) 0.111(4) 0.136(4) 0.019(4) 0.036(3) 0.008(3)
C29 0.062(3) 0.050(2) 0.162(6) 0.005(3) -0.037(4) -0.017(2)
O30 0.0503(17) 0.0468(16) 0.073(2) 0.0202(14) -0.0057(15) -0.0111(13)
C14 0.048(3) 0.150(5) 0.102(3) -0.047(4) 0.019(3) -0.004(3)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.5464(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.210(4) yes
C2 . C3 . 1.506(5) yes
C2 . N23 . 1.408(4) yes
C3 . C4 . 1.525(5) yes
C3 . H31 . 1.000 no
C3 . H32 . 1.000 no
C4 . C5 . 1.490(5) yes
C4 . H41 . 1.000 no
C4 . H42 . 0.998 no
C5 . C6 . 1.304(5) yes
C5 . H51 . 1.004 no
C6 . C7 . 1.499(5) yes
C6 . H61 . 0.999 no
C7 . N8 . 1.471(5) yes
C7 . H71 . 1.000 no
C7 . H72 . 1.001 no
N8 . C9 . 1.415(5) yes
N8 . C17 . 1.401(5) yes
C9 . O10 . 1.307(4) yes
C9 . O15 . 1.206(5) yes
O10 . C11 . 1.485(4) yes
C11 . C12 . 1.499(6) yes
C11 . C13 . 1.494(7) yes
C11 . C14 . 1.490(6) yes
C12 . H121 . 0.999 no
C12 . H122 . 1.006 no
C12 . H123 . 0.994 no
C13 . H131 . 1.000 no
C13 . H132 . 1.001 no
C13 . H133 . 1.002 no
O16 . C17 . 1.216(4) yes
C17 . C18 . 1.504(5) yes
C18 . C19 . 1.518(5) yes
C18 . H181 . 1.000 no
C18 . H182 . 1.001 no
C19 . C20 . 1.473(5) yes
C19 . H191 . 1.001 no
C19 . H192 . 1.003 no
C20 . C21 . 1.319(5) yes
C20 . H201 . 1.003 no
C21 . C22 . 1.497(5) yes
C21 . H211 . 1.000 no
C22 . N23 . 1.471(5) yes
C22 . H221 . 0.999 no
C22 . H222 . 1.002 no
N23 . C24 . 1.399(4) yes
C24 . O25 . 1.323(4) yes
C24 . O30 . 1.207(5) yes
O25 . C26 . 1.482(4) yes
C26 . C27 . 1.504(7) yes
C26 . C28 . 1.480(8) yes
C26 . C29 . 1.519(6) yes
C27 . H271 . 0.999 no
C27 . H272 . 0.998 no
C27 . H273 . 1.007 no
C28 . H281 . 0.999 no
C28 . H282 . 1.002 no
C28 . H283 . 1.001 no
C29 . H291 . 0.997 no
C29 . H292 . 0.999 no
C29 . H293 . 1.003 no
C14 . H141 . 1.000 no
C14 . H142 . 0.998 no
C14 . H143 . 1.001 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . C3 . 121.2(3) yes
O1 . C2 . N23 . 118.4(3) yes
C3 . C2 . N23 . 120.4(3) yes
C2 . C3 . C4 . 110.8(3) yes
C2 . C3 . H31 . 109.207 no
C4 . C3 . H31 . 109.063 no
C2 . C3 . H32 . 109.254 no
C4 . C3 . H32 . 108.927 no
H31 . C3 . H32 . 109.545 no
C3 . C4 . C5 . 112.6(3) yes
C3 . C4 . H41 . 108.665 no
C5 . C4 . H41 . 108.433 no
C3 . C4 . H42 . 108.712 no
C5 . C4 . H42 . 108.740 no
H41 . C4 . H42 . 109.636 no
C4 . C5 . C6 . 127.1(4) yes
C4 . C5 . H51 . 116.426 no
C6 . C5 . H51 . 116.508 no
C5 . C6 . C7 . 127.3(4) yes
C5 . C6 . H61 . 116.208 no
C7 . C6 . H61 . 116.508 no
C6 . C7 . N8 . 113.0(3) yes
C6 . C7 . H71 . 108.647 no
N8 . C7 . H71 . 108.685 no
C6 . C7 . H72 . 108.567 no
N8 . C7 . H72 . 108.585 no
H71 . C7 . H72 . 109.356 no
C7 . N8 . C9 . 119.9(3) yes
C7 . N8 . C17 . 116.9(3) yes
C9 . N8 . C17 . 123.2(3) yes
N8 . C9 . O10 . 109.4(3) yes
N8 . C9 . O15 . 123.8(4) yes
O10 . C9 . O15 . 126.8(4) yes
C9 . O10 . C11 . 121.0(3) yes
O10 . C11 . C12 . 110.9(3) yes
O10 . C11 . C13 . 101.8(4) yes
C12 . C11 . C13 . 110.2(4) yes
O10 . C11 . C14 . 107.8(4) yes
C12 . C11 . C14 . 113.6(5) yes
C13 . C11 . C14 . 111.9(4) yes
C11 . C12 . H121 . 109.516 no
C11 . C12 . H122 . 109.029 no
H121 . C12 . H122 . 109.062 no
C11 . C12 . H123 . 109.743 no
H121 . C12 . H123 . 110.027 no
H122 . C12 . H123 . 109.443 no
C11 . C13 . H131 . 109.710 no
C11 . C13 . H132 . 109.546 no
H131 . C13 . H132 . 109.380 no
C11 . C13 . H133 . 109.628 no
H131 . C13 . H133 . 109.346 no
H132 . C13 . H133 . 109.216 no
N8 . C17 . O16 . 118.0(4) yes
N8 . C17 . C18 . 120.4(3) yes
O16 . C17 . C18 . 121.5(4) yes
C17 . C18 . C19 . 111.5(3) yes
C17 . C18 . H181 . 109.044 no
C19 . C18 . H181 . 109.080 no
C17 . C18 . H182 . 108.966 no
C19 . C18 . H182 . 108.876 no
H181 . C18 . H182 . 109.393 no
C18 . C19 . C20 . 113.0(3) yes
C18 . C19 . H191 . 108.593 no
C20 . C19 . H191 . 108.882 no
C18 . C19 . H192 . 108.548 no
C20 . C19 . H192 . 108.595 no
H191 . C19 . H192 . 109.151 no
C19 . C20 . C21 . 126.2(4) yes
C19 . C20 . H201 . 116.770 no
C21 . C20 . H201 . 117.021 no
C20 . C21 . C22 . 127.3(4) yes
C20 . C21 . H211 . 116.439 no
C22 . C21 . H211 . 116.277 no
C21 . C22 . N23 . 113.0(3) yes
C21 . C22 . H221 . 108.698 no
N23 . C22 . H221 . 108.737 no
C21 . C22 . H222 . 108.513 no
N23 . C22 . H222 . 108.551 no
H221 . C22 . H222 . 109.336 no
C22 . N23 . C2 . 115.9(3) yes
C22 . N23 . C24 . 120.2(3) yes
C2 . N23 . C24 . 123.9(3) yes
N23 . C24 . O25 . 108.8(3) yes
N23 . C24 . O30 . 124.5(4) yes
O25 . C24 . O30 . 126.6(4) yes
C24 . O25 . C26 . 122.3(3) yes
O25 . C26 . C27 . 101.5(4) yes
O25 . C26 . C28 . 109.1(4) yes
C27 . C26 . C28 . 111.4(4) yes
O25 . C26 . C29 . 108.8(4) yes
C27 . C26 . C29 . 112.6(5) yes
C28 . C26 . C29 . 112.8(5) yes
C26 . C27 . H271 . 109.721 no
C26 . C27 . H272 . 109.752 no
H271 . C27 . H272 . 109.720 no
C26 . C27 . H273 . 109.522 no
H271 . C27 . H273 . 109.012 no
H272 . C27 . H273 . 109.096 no
C26 . C28 . H281 . 109.599 no
C26 . C28 . H282 . 109.594 no
H281 . C28 . H282 . 109.402 no
C26 . C28 . H283 . 109.463 no
H281 . C28 . H283 . 109.491 no
H282 . C28 . H283 . 109.277 no
C26 . C29 . H291 . 109.462 no
C26 . C29 . H292 . 109.521 no
H291 . C29 . H292 . 109.783 no
C26 . C29 . H293 . 109.346 no
H291 . C29 . H293 . 109.425 no
H292 . C29 . H293 . 109.289 no
C11 . C14 . H141 . 109.364 no
C11 . C14 . H142 . 109.553 no
H141 . C14 . H142 . 109.612 no
C11 . C14 . H143 . 109.294 no
H141 . C14 . H143 . 109.409 no
H142 . C14 . H143 . 109.594 no
# Attachment 'Supporting_Information_for_Publication__compound_7a_.cif.txt'
data_s2828
_database_code_depnum_ccdc_archive 'CCDC 766490'
#TrackingRef 'Supporting_Information_for_Publication__compound_7a_.cif.txt'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_publ_section_abstract
;
?
;
_publ_section_exptl_prep
;
?
;
_publ_section_exptl_refinement
;
The structure was solved by the direct methods.
All non-H atoms were refined anisotropically.
H atoms were included in calculated positions,
except the one bonded to N1, which was found
by difference Fourier techniques and refined isotropically.
;
_publ_section_comment
;
?
;
_publ_section_references
;
Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.;
Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna,
R. J. Appl. Cryst. 1999, 32, 115-119.
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
;
?
;
_publ_section_table_legends
;
?
;
_publ_section_figure_captions
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C11 H19 N O4'
_chemical_formula_weight 229.27
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 21.933(4)
_cell_length_b 5.6050(9)
_cell_length_c 10.1718(17)
_cell_angle_alpha 90.00
_cell_angle_beta 98.548(3)
_cell_angle_gamma 90.00
_cell_volume 1236.5(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 2042
_cell_measurement_theta_min 2.82
_cell_measurement_theta_max 26.13
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.65
_exptl_crystal_size_mid 0.60
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.232
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 496
_exptl_absorpt_coefficient_mu 0.093
_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 6594
_diffrn_reflns_av_R_equivalents 0.0825
_diffrn_reflns_av_sigmaI/netI 0.0702
_diffrn_reflns_limit_h_min -26
_diffrn_reflns_limit_h_max 27
_diffrn_reflns_limit_k_min -6
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 1.88
_diffrn_reflns_theta_max 26.39
_reflns_number_total 2516
_reflns_number_gt 1931
_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^)+(0.0525P)^2^+0.0743P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2516
_refine_ls_number_parameters 153
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0708
_refine_ls_R_factor_gt 0.0499
_refine_ls_wR_factor_ref 0.1232
_refine_ls_wR_factor_gt 0.1144
_refine_ls_goodness_of_fit_ref 1.040
_refine_ls_restrained_S_all 1.040
_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 0.15660(5) 0.4079(2) 0.28092(12) 0.0238(3) Uani 1 1 d . . .
O2 O 0.22369(5) 0.2571(2) 0.15077(12) 0.0226(3) Uani 1 1 d . . .
O3 O 0.50051(6) -0.2609(2) 0.89148(13) 0.0297(3) Uani 1 1 d . . .
H3 H 0.5192 -0.1943 0.9598 0.045 Uiso 1 1 calc R . .
O4 O 0.43995(5) 0.0607(2) 0.88941(12) 0.0265(3) Uani 1 1 d . . .
N1 N 0.24281(7) 0.2398(3) 0.37577(17) 0.0226(4) Uani 1 1 d . . .
C1 C 0.11618(8) 0.5222(3) 0.17049(18) 0.0222(4) Uani 1 1 d . . .
C2 C 0.06834(8) 0.6438(4) 0.2418(2) 0.0330(5) Uani 1 1 d . . .
H2A H 0.0496 0.5257 0.2946 0.049 Uiso 1 1 calc R . .
H2B H 0.0363 0.7152 0.1762 0.049 Uiso 1 1 calc R . .
H2C H 0.0883 0.7686 0.3005 0.049 Uiso 1 1 calc R . .
C3 C 0.15147(9) 0.7054(3) 0.1028(2) 0.0312(5) Uani 1 1 d . . .
H3A H 0.1742 0.8104 0.1698 0.047 Uiso 1 1 calc R . .
H3B H 0.1225 0.8004 0.0412 0.047 Uiso 1 1 calc R . .
H3C H 0.1805 0.6241 0.0534 0.047 Uiso 1 1 calc R . .
C4 C 0.08606(9) 0.3349(4) 0.0745(2) 0.0327(5) Uani 1 1 d . . .
H4A H 0.1176 0.2572 0.0304 0.049 Uiso 1 1 calc R . .
H4B H 0.0554 0.4111 0.0077 0.049 Uiso 1 1 calc R . .
H4C H 0.0657 0.2155 0.1235 0.049 Uiso 1 1 calc R . .
C5 C 0.20894(8) 0.2973(3) 0.25931(17) 0.0175(4) Uani 1 1 d . . .
C6 C 0.30096(8) 0.1119(3) 0.38442(19) 0.0243(4) Uani 1 1 d . . .
H6A H 0.3330 0.1990 0.4446 0.029 Uiso 1 1 calc R . .
H6B H 0.3139 0.1058 0.2953 0.029 Uiso 1 1 calc R . .
C7 C 0.29565(8) -0.1368(3) 0.43516(18) 0.0232(4) Uani 1 1 d . . .
H7 H 0.2713 -0.2451 0.3776 0.028 Uiso 1 1 calc R . .
C8 C 0.32127(8) -0.2213(3) 0.55162(18) 0.0236(4) Uani 1 1 d . . .
H8 H 0.3136 -0.3848 0.5677 0.028 Uiso 1 1 calc R . .
C9 C 0.36075(8) -0.0916(3) 0.66109(18) 0.0232(4) Uani 1 1 d . . .
H9A H 0.3364 -0.0594 0.7337 0.028 Uiso 1 1 calc R . .
H9B H 0.3732 0.0638 0.6272 0.028 Uiso 1 1 calc R . .
C10 C 0.41825(8) -0.2316(3) 0.71648(18) 0.0244(4) Uani 1 1 d . . .
H10A H 0.4061 -0.3968 0.7352 0.029 Uiso 1 1 calc R . .
H10B H 0.4458 -0.2398 0.6478 0.029 Uiso 1 1 calc R . .
C11 C 0.45335(8) -0.1282(3) 0.84028(18) 0.0227(4) Uani 1 1 d . . .
H1N H 0.2297(9) 0.264(4) 0.443(2) 0.024(6) 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 0.0258(7) 0.0276(7) 0.0181(7) 0.0040(6) 0.0035(5) 0.0071(5)
O2 0.0285(7) 0.0256(7) 0.0138(6) 0.0005(6) 0.0033(5) 0.0019(5)
O3 0.0289(7) 0.0325(8) 0.0246(8) -0.0044(6) -0.0068(6) 0.0080(6)
O4 0.0264(7) 0.0284(8) 0.0231(7) -0.0026(6) -0.0012(5) 0.0053(6)
N1 0.0274(8) 0.0268(9) 0.0141(8) 0.0013(7) 0.0043(7) 0.0066(7)
C1 0.0228(9) 0.0218(9) 0.0203(10) 0.0010(8) -0.0020(7) 0.0044(7)
C2 0.0312(11) 0.0348(12) 0.0316(12) -0.0019(10) 0.0007(9) 0.0120(9)
C3 0.0368(11) 0.0224(10) 0.0330(12) 0.0057(9) 0.0007(9) 0.0022(8)
C4 0.0290(10) 0.0272(10) 0.0385(12) -0.0069(10) -0.0060(9) 0.0018(9)
C5 0.0210(9) 0.0134(8) 0.0179(9) 0.0011(7) 0.0024(7) -0.0022(7)
C6 0.0243(9) 0.0280(11) 0.0202(10) 0.0042(8) 0.0018(7) 0.0029(8)
C7 0.0237(9) 0.0219(10) 0.0229(10) -0.0055(8) 0.0003(7) 0.0025(8)
C8 0.0246(10) 0.0192(9) 0.0260(10) 0.0010(8) 0.0008(8) 0.0013(7)
C9 0.0243(9) 0.0255(10) 0.0191(10) 0.0009(8) 0.0007(7) 0.0031(8)
C10 0.0259(10) 0.0258(10) 0.0210(10) 0.0020(8) 0.0015(8) 0.0009(8)
C11 0.0203(9) 0.0281(10) 0.0196(9) 0.0029(9) 0.0027(7) 0.0001(8)
_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 1.351(2) . ?
O1 C1 1.470(2) . ?
O2 C5 1.217(2) . ?
O3 C11 1.317(2) . ?
O3 H3 0.8400 . ?
O4 C11 1.225(2) . ?
N1 C5 1.341(2) . ?
N1 C6 1.454(2) . ?
N1 H1N 0.79(2) . ?
C1 C3 1.512(3) . ?
C1 C4 1.516(3) . ?
C1 C2 1.522(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 C7 1.497(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.321(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.494(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.521(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.492(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C1 120.40(13) . . ?
C11 O3 H3 109.5 . . ?
C5 N1 C6 122.53(16) . . ?
C5 N1 H1N 119.7(14) . . ?
C6 N1 H1N 117.5(14) . . ?
O1 C1 C3 110.64(14) . . ?
O1 C1 C4 110.23(15) . . ?
C3 C1 C4 112.36(16) . . ?
O1 C1 C2 102.18(14) . . ?
C3 C1 C2 110.41(16) . . ?
C4 C1 C2 110.58(15) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C5 N1 124.76(16) . . ?
O2 C5 O1 125.41(16) . . ?
N1 C5 O1 109.82(15) . . ?
N1 C6 C7 111.56(15) . . ?
N1 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 126.77(18) . . ?
C8 C7 H7 116.6 . . ?
C6 C7 H7 116.6 . . ?
C7 C8 C9 128.02(17) . . ?
C7 C8 H8 116.0 . . ?
C9 C8 H8 116.0 . . ?
C8 C9 C10 112.45(15) . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 114.05(15) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
O4 C11 O3 123.30(17) . . ?
O4 C11 C10 123.72(16) . . ?
O3 C11 C10 112.98(16) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 C3 -56.5(2) . . . . ?
C5 O1 C1 C4 68.4(2) . . . . ?
C5 O1 C1 C2 -174.06(15) . . . . ?
C6 N1 C5 O2 -2.6(3) . . . . ?
C6 N1 C5 O1 178.04(15) . . . . ?
C1 O1 C5 O2 -9.0(3) . . . . ?
C1 O1 C5 N1 170.43(14) . . . . ?
C5 N1 C6 C7 -110.1(2) . . . . ?
N1 C6 C7 C8 -110.7(2) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C7 C8 C9 C10 -133.45(19) . . . . ?
C8 C9 C10 C11 -170.24(16) . . . . ?
C9 C10 C11 O4 -4.5(3) . . . . ?
C9 C10 C11 O3 175.61(15) . . . . ?
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 H1N O2 0.79(2) 2.14(2) 2.890(2) 157.8(19) 4_566
O3 H3 O4 0.84 1.82 2.6584(18) 177.9 3_657
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full 26.39
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max 0.247
_refine_diff_density_min -0.179
_refine_diff_density_rms 0.047