# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010
data_global
_journal_name_full CrystEngComm
_journal_coden_Cambridge 1350
_journal_volume ?
_journal_page_first ?
_journal_year ?
_publ_contact_author_name 'Shyamaprosad Goswami'
_publ_contact_author_email SPGOSWAMICAL@YAHOO.COM
_publ_section_title
;
Recognition Study of Substituted Benzoic Acids
by 7-Substituted Pterin Receptors in Solution and Solid Phases
;
loop_
_publ_author_name
'Shyamaprosad Goswami'
'Hoong-Kun Fun.'
'Anita Hazra'
'Subrata Janaa'
data_fs47_0m
_database_code_depnum_ccdc_archive 'CCDC 742682'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety '2(C12 H15 N5 O2), 3(C7 H6 O3)'
_chemical_formula_sum 'C45 H48 N10 O13'
_chemical_formula_weight 936.93
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_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 21/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 16.0828(9)
_cell_length_b 6.8716(3)
_cell_length_c 24.8286(14)
_cell_angle_alpha 90.00
_cell_angle_beta 121.643(4)
_cell_angle_gamma 90.00
_cell_volume 2336.0(2)
_cell_formula_units_Z 2
_cell_measurement_temperature 100
_cell_measurement_reflns_used 4484
_cell_measurement_theta_min 2.56
_cell_measurement_theta_max 30.14
_exptl_crystal_description block
_exptl_crystal_colour brown
_exptl_crystal_size_max 0.38
_exptl_crystal_size_mid 0.14
_exptl_crystal_size_min 0.05
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.332
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 984
_exptl_absorpt_coefficient_mu 0.100
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9635
_exptl_absorpt_correction_T_max 0.9950
_exptl_absorpt_process_details '(SADABS; Bruker, 2005)'
_exptl_special_details
; The crystal was placed in the cold stream of an Oxford Cyrosystems
Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating
at 100.0(1)K.
;
_diffrn_ambient_temperature 100
_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
; Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 17050
_diffrn_reflns_av_R_equivalents 0.0594
_diffrn_reflns_av_sigmaI/netI 0.0511
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_l_min -26
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_theta_min 2.56
_diffrn_reflns_theta_max 22.50
_reflns_number_total 3046
_reflns_number_gt 2121
_reflns_threshold_expression I>2\(I)
_computing_data_collection 'APEX2 (Bruker, 2005)'
_computing_cell_refinement APEX2
_computing_data_reduction 'SAINT (Bruker, 2005)'
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement SHELXTL
_computing_molecular_graphics SHELXTL
_computing_publication_material
; SHELXTL (
Sheldrick, 2008), PLATON (
Spek, 2003)
;
_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 Rfactors
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^)+(0.1316P)^2^+7.4363P] 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 3046
_refine_ls_number_parameters 317
_refine_ls_number_restraints 122
_refine_ls_R_factor_all 0.1181
_refine_ls_R_factor_gt 0.0875
_refine_ls_wR_factor_ref 0.2599
_refine_ls_wR_factor_gt 0.2372
_refine_ls_goodness_of_fit_ref 1.051
_refine_ls_restrained_S_all 1.034
_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
O1A O 0.1232(3) 0.3140(6) 0.22494(18) 0.0393(11) Uani 1 1 d . . .
O2A O 0.4147(3) 0.4415(5) 0.27185(16) 0.0334(10) Uani 1 1 d . . .
N1A N 0.2530(3) 0.1789(6) 0.4438(2) 0.0318(12) Uani 1 1 d . . .
N2A N 0.0883(3) 0.1889(6) 0.3193(2) 0.0324(12) Uani 1 1 d . . .
N3A N 0.3540(3) 0.2662(6) 0.4076(2) 0.0227(11) Uani 1 1 d . . .
N4A N 0.2851(3) 0.3346(6) 0.2991(2) 0.0252(11) Uani 1 1 d . . .
H1N4 H 0.2921 0.3781 0.2667 0.08(3) Uiso 1 1 d R . .
N5A N 0.4539(3) 0.3499(6) 0.37091(19) 0.0231(11) Uani 1 1 d . . .
H1N5 H 0.5008 0.3391 0.4113 0.031(15) Uiso 1 1 d R . .
C1A C 0.1510(5) 0.0923(11) 0.4839(3) 0.0559(19) Uani 1 1 d . . .
H1AA H 0.2061 0.0191 0.5153 0.084 Uiso 1 1 calc R . .
H1AB H 0.0926 0.0169 0.4687 0.084 Uiso 1 1 calc R . .
H1AC H 0.1458 0.2111 0.5022 0.084 Uiso 1 1 calc R . .
C2A C 0.1640(4) 0.1374(8) 0.4313(3) 0.0359(15) Uani 1 1 d . . .
C3A C 0.0820(4) 0.1407(8) 0.3674(3) 0.0328(14) Uani 1 1 d . . .
H3AA H 0.0194 0.1028 0.3600 0.039 Uiso 1 1 d R . .
C4A C 0.1784(3) 0.2363(7) 0.3315(3) 0.0279(14) Uani 1 1 d . . .
C5A C 0.2607(4) 0.2284(7) 0.3938(3) 0.0261(13) Uani 1 1 d . . .
C6A C 0.3622(3) 0.3151(7) 0.3599(2) 0.0213(12) Uani 1 1 d . . .
C7A C 0.1891(4) 0.2963(7) 0.2803(3) 0.0281(13) Uani 1 1 d . . .
C8A C 0.4777(4) 0.4065(7) 0.3268(2) 0.0249(13) Uani 1 1 d . . .
C9A C 0.5863(4) 0.4201(8) 0.3519(2) 0.0299(14) Uani 1 1 d . . .
C10A C 0.6342(4) 0.5745(9) 0.4045(3) 0.0395(15) Uani 1 1 d . . .
H10A H 0.6296 0.5342 0.4399 0.059 Uiso 1 1 calc R . .
H10B H 0.6013 0.6967 0.3888 0.059 Uiso 1 1 calc R . .
H10C H 0.7017 0.5888 0.4178 0.059 Uiso 1 1 calc R . .
C11A C 0.6332(4) 0.2192(9) 0.3775(3) 0.0399(15) Uani 1 1 d . . .
H11A H 0.6042 0.1254 0.3439 0.060 Uiso 1 1 calc R . .
H11B H 0.6225 0.1803 0.4105 0.060 Uiso 1 1 calc R . .
H11C H 0.7021 0.2267 0.3941 0.060 Uiso 1 1 calc R . .
C12A C 0.5993(4) 0.4802(10) 0.2976(3) 0.0445(17) Uani 1 1 d . . .
H12A H 0.5706 0.3835 0.2648 0.067 Uiso 1 1 calc R . .
H12B H 0.6677 0.4917 0.3128 0.067 Uiso 1 1 calc R . .
H12C H 0.5678 0.6031 0.2809 0.067 Uiso 1 1 calc R . .
O3A O 0.0698(3) 0.6736(5) 0.31079(18) 0.0256(9) Uani 1 1 d DU . .
O4A O 0.4051(2) 0.7037(6) 0.50089(17) 0.0336(10) Uani 1 1 d DU . .
O5A O 0.5011(3) 0.7875(5) 0.46441(19) 0.0291(10) Uani 1 1 d DU . .
C13A C 0.3411(4) 0.8222(7) 0.3411(2) 0.0219(12) Uani 1 1 d DU . .
H13A H 0.4043 0.8534 0.3484 0.026 Uiso 1 1 d R . .
C14A C 0.2596(4) 0.8338(7) 0.2812(2) 0.0239(12) Uani 1 1 d DU . .
H14A H 0.2662 0.8743 0.2466 0.029 Uiso 1 1 d R . .
C15A C 0.1679(4) 0.7880(7) 0.2696(2) 0.0210(12) Uani 1 1 d DU . .
H15A H 0.1115 0.7991 0.2277 0.025 Uiso 1 1 d R . .
C16A C 0.1574(3) 0.7270(7) 0.3190(2) 0.0183(11) Uani 1 1 d DU . .
C17A C 0.2395(3) 0.7154(7) 0.3795(2) 0.0190(11) Uani 1 1 d DU . .
H17A H 0.2324 0.6743 0.4139 0.023 Uiso 1 1 d R . .
C18A C 0.3311(3) 0.7632(7) 0.3912(2) 0.0174(11) Uani 1 1 d DU . .
C19A C 0.4160(3) 0.7495(7) 0.4575(2) 0.0209(12) Uani 1 1 d DU . .
O3B O -0.0851(9) 1.1968(17) 0.0752(6) 0.083(4) Uiso 0.50 1 d PDU . .
H5BA H -0.0686 1.2044 0.1158 0.100 Uiso 0.50 1 d PR . .
O4B O -0.0935(11) 1.046(2) -0.1268(6) 0.110(5) Uiso 0.50 1 d PDU . .
O5B O 0.0335(10) 0.853(2) -0.0925(6) 0.094(4) Uiso 0.50 1 d PDU . .
H5BB H 0.0128 0.8534 -0.1365 0.141 Uiso 0.50 1 d PR . .
C13B C 0.0809(10) 0.869(2) 0.0302(6) 0.065(4) Uiso 0.50 1 d PDU . .
H13B H 0.1211 0.7937 0.0201 0.078 Uiso 0.50 1 d PR . .
C14B C 0.1062(10) 0.875(2) 0.0925(6) 0.066(4) Uiso 0.50 1 d PDU . .
H14B H 0.1598 0.8009 0.1246 0.079 Uiso 0.50 1 d PR . .
C15B C 0.0501(12) 0.980(3) 0.1097(8) 0.066(5) Uiso 0.50 1 d PDU . .
H15B H 0.0683 0.9924 0.1531 0.079 Uiso 0.50 1 d PR . .
C16B C -0.0296(10) 1.0833(19) 0.0626(6) 0.049(4) Uiso 0.50 1 d PDU . .
C17B C -0.0558(11) 1.066(2) -0.0012(7) 0.070(5) Uiso 0.50 1 d PDU . .
H17B H -0.1123 1.1331 -0.0339 0.084 Uiso 0.50 1 d PR . .
C18B C -0.0004(9) 0.9667(18) -0.0174(5) 0.043(3) Uiso 0.50 1 d PDU . .
C19B C -0.0292(11) 0.950(2) -0.0854(6) 0.058(4) Uiso 0.50 1 d PDU . .
H1O3 H 0.025(5) 0.681(10) 0.275(3) 0.06(2) Uiso 1 1 d . . .
H1O5 H 0.538(5) 0.764(10) 0.505(3) 0.06(2) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1A 0.020(2) 0.041(3) 0.036(2) -0.0040(19) 0.000(2) -0.0014(18)
O2A 0.028(2) 0.042(2) 0.024(2) 0.0030(18) 0.0090(19) 0.0084(18)
N1A 0.022(3) 0.026(3) 0.042(3) -0.008(2) 0.013(2) -0.006(2)
N2A 0.026(3) 0.021(3) 0.046(3) -0.002(2) 0.016(2) -0.002(2)
N3A 0.012(2) 0.019(2) 0.031(3) -0.009(2) 0.007(2) -0.0020(18)
N4A 0.016(2) 0.020(2) 0.026(3) -0.006(2) 0.001(2) -0.0003(19)
N5A 0.012(2) 0.025(2) 0.021(2) -0.0043(19) 0.001(2) 0.0020(19)
C1A 0.041(4) 0.072(5) 0.044(4) 0.003(4) 0.015(3) -0.010(4)
C2A 0.035(4) 0.027(3) 0.053(4) -0.003(3) 0.028(3) -0.004(3)
C3A 0.013(3) 0.028(3) 0.048(4) -0.006(3) 0.010(3) 0.002(2)
C4A 0.007(3) 0.017(3) 0.045(4) -0.010(3) 0.003(3) -0.001(2)
C5A 0.020(3) 0.016(3) 0.039(3) -0.007(2) 0.013(3) -0.001(2)
C6A 0.017(3) 0.012(3) 0.026(3) -0.006(2) 0.005(2) -0.001(2)
C7A 0.019(3) 0.021(3) 0.032(3) -0.004(3) 0.005(3) 0.002(2)
C8A 0.027(3) 0.021(3) 0.023(3) -0.002(2) 0.011(3) 0.007(2)
C9A 0.029(3) 0.034(3) 0.027(3) -0.003(3) 0.015(3) 0.003(3)
C10A 0.035(3) 0.044(4) 0.047(4) -0.013(3) 0.026(3) -0.009(3)
C11A 0.028(3) 0.049(4) 0.041(3) 0.000(3) 0.017(3) 0.011(3)
C12A 0.039(4) 0.063(4) 0.042(4) 0.005(3) 0.028(3) 0.007(3)
O3A 0.0117(19) 0.036(2) 0.023(2) 0.0030(18) 0.0046(17) -0.0002(17)
O4A 0.018(2) 0.051(3) 0.025(2) 0.0016(18) 0.0060(17) -0.0036(18)
O5A 0.016(2) 0.041(2) 0.026(2) -0.0061(19) 0.0082(18) -0.0015(17)
C13A 0.022(3) 0.014(3) 0.033(3) -0.006(2) 0.017(2) -0.001(2)
C14A 0.029(3) 0.025(3) 0.021(3) -0.003(2) 0.016(2) -0.001(2)
C15A 0.020(3) 0.018(3) 0.018(3) 0.001(2) 0.005(2) 0.001(2)
C16A 0.015(3) 0.015(3) 0.024(3) -0.003(2) 0.009(2) 0.001(2)
C17A 0.018(3) 0.020(3) 0.016(2) -0.002(2) 0.007(2) 0.000(2)
C18A 0.016(2) 0.012(3) 0.021(2) -0.002(2) 0.008(2) 0.003(2)
C19A 0.014(3) 0.017(3) 0.027(3) -0.006(2) 0.008(2) -0.001(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
O1A C7A 1.225(6) . ?
O2A C8A 1.224(6) . ?
N1A C2A 1.327(7) . ?
N1A C5A 1.354(7) . ?
N2A C3A 1.294(7) . ?
N2A C4A 1.355(6) . ?
N3A C6A 1.302(6) . ?
N3A C5A 1.379(6) . ?
N4A C6A 1.367(6) . ?
N4A C7A 1.383(7) . ?
N4A H1N4 0.9194 . ?
N5A C6A 1.373(6) . ?
N5A C8A 1.391(7) . ?
N5A H1N5 0.8858 . ?
C1A C2A 1.460(8) . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
C2A C3A 1.435(8) . ?
C3A H3AA 0.9599 . ?
C4A C5A 1.414(7) . ?
C4A C7A 1.431(8) . ?
C8A C9A 1.518(7) . ?
C9A C12A 1.526(8) . ?
C9A C10A 1.540(8) . ?
C9A C11A 1.542(8) . ?
C10A H10A 0.9600 . ?
C10A H10B 0.9600 . ?
C10A H10C 0.9600 . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
O3A C16A 1.364(6) . ?
O3A H1O3 0.79(7) . ?
O4A C19A 1.220(6) . ?
O5A C19A 1.312(6) . ?
O5A H1O5 0.87(7) . ?
C13A C14A 1.374(7) . ?
C13A C18A 1.395(7) . ?
C13A H13A 0.9600 . ?
C14A C15A 1.382(7) . ?
C14A H14A 0.9603 . ?
C15A C16A 1.387(7) . ?
C15A H15A 0.9600 . ?
C16A C17A 1.388(7) . ?
C17A C18A 1.385(7) . ?
C17A H17A 0.9600 . ?
C18A C19A 1.492(6) . ?
O3B O5B 0.784(14) 3_575 ?
O3B C16B 1.340(14) . ?
O3B H5BA 0.9000 . ?
O4B C15B 0.624(19) 3_575 ?
O4B C14B 1.114(17) 3_575 ?
O4B C19B 1.203(15) . ?
O5B O3B 0.784(14) 3_575 ?
O5B C16B 0.892(15) 3_575 ?
O5B C19B 1.296(14) . ?
O5B C15B 1.645(19) 3_575 ?
O5B H5BB 0.9600 . ?
C13B C17B 0.758(18) 3_575 ?
C13B C14B 1.377(14) . ?
C13B C18B 1.391(15) . ?
C13B C18B 1.617(19) 3_575 ?
C13B C16B 2.027(17) 3_575 ?
C13B H13B 0.9601 . ?
C14B O4B 1.114(17) 3_575 ?
C14B C15B 1.385(15) . ?
C14B C19B 1.67(2) 3_575 ?
C14B C17B 2.006(18) 3_575 ?
C14B H14B 0.9600 . ?
C15B O4B 0.624(19) 3_575 ?
C15B C19B 0.706(18) 3_575 ?
C15B C16B 1.393(16) . ?
C15B O5B 1.645(19) 3_575 ?
C15B C18B 2.026(19) 3_575 ?
C15B H15B 0.9598 . ?
C16B C19B 0.839(16) 3_575 ?
C16B O5B 0.892(15) 3_575 ?
C16B C17B 1.416(14) . ?
C16B C18B 1.476(16) 3_575 ?
C16B C13B 2.027(17) 3_575 ?
C17B C13B 0.758(18) 3_575 ?
C17B C18B 0.802(17) 3_575 ?
C17B C18B 1.340(15) . ?
C17B C19B 1.849(19) 3_575 ?
C17B C17B 1.98(3) 3_575 ?
C17B C14B 2.006(18) 3_575 ?
C17B H17B 0.9600 . ?
C18B C17B 0.802(17) 3_575 ?
C18B C18B 0.973(18) 3_575 ?
C18B C16B 1.476(16) 3_575 ?
C18B C19B 1.501(13) . ?
C18B C13B 1.617(19) 3_575 ?
C18B C15B 2.026(19) 3_575 ?
C19B C15B 0.706(18) 3_575 ?
C19B C16B 0.839(16) 3_575 ?
C19B C14B 1.67(2) 3_575 ?
C19B C17B 1.849(19) 3_575 ?
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
C2A N1A C5A 116.4(5) . . ?
C3A N2A C4A 116.5(5) . . ?
C6A N3A C5A 116.1(4) . . ?
C6A N4A C7A 124.0(5) . . ?
C6A N4A H1N4 122.8 . . ?
C7A N4A H1N4 113.2 . . ?
C6A N5A C8A 127.0(4) . . ?
C6A N5A H1N5 113.4 . . ?
C8A N5A H1N5 119.4 . . ?
C2A C1A H1AA 109.5 . . ?
C2A C1A H1AB 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
C2A C1A H1AC 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
N1A C2A C3A 120.5(5) . . ?
N1A C2A C1A 118.6(5) . . ?
C3A C2A C1A 120.8(5) . . ?
N2A C3A C2A 123.6(5) . . ?
N2A C3A H3AA 118.2 . . ?
C2A C3A H3AA 118.1 . . ?
N2A C4A C5A 120.9(5) . . ?
N2A C4A C7A 118.9(5) . . ?
C5A C4A C7A 120.2(5) . . ?
N1A C5A N3A 115.5(5) . . ?
N1A C5A C4A 122.0(5) . . ?
N3A C5A C4A 122.5(5) . . ?
N3A C6A N4A 124.3(5) . . ?
N3A C6A N5A 118.3(4) . . ?
N4A C6A N5A 117.4(5) . . ?
O1A C7A N4A 121.1(5) . . ?
O1A C7A C4A 126.0(5) . . ?
N4A C7A C4A 112.9(5) . . ?
O2A C8A N5A 121.6(5) . . ?
O2A C8A C9A 123.1(5) . . ?
N5A C8A C9A 115.3(4) . . ?
C8A C9A C12A 108.4(4) . . ?
C8A C9A C10A 110.2(4) . . ?
C12A C9A C10A 108.9(5) . . ?
C8A C9A C11A 108.8(4) . . ?
C12A C9A C11A 110.0(5) . . ?
C10A C9A C11A 110.4(4) . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
C9A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C9A C11A H11A 109.5 . . ?
C9A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C9A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C9A C12A H12A 109.5 . . ?
C9A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C9A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C16A O3A H1O3 115(5) . . ?
C19A O5A H1O5 99(4) . . ?
C14A C13A C18A 119.4(5) . . ?
C14A C13A H13A 120.4 . . ?
C18A C13A H13A 120.2 . . ?
C13A C14A C15A 121.3(5) . . ?
C13A C14A H14A 119.6 . . ?
C15A C14A H14A 119.0 . . ?
C14A C15A C16A 119.7(4) . . ?
C14A C15A H15A 120.4 . . ?
C16A C15A H15A 119.9 . . ?
O3A C16A C15A 123.0(4) . . ?
O3A C16A C17A 117.8(4) . . ?
C15A C16A C17A 119.2(4) . . ?
C18A C17A C16A 121.0(5) . . ?
C18A C17A H17A 119.6 . . ?
C16A C17A H17A 119.4 . . ?
C17A C18A C13A 119.3(4) . . ?
C17A C18A C19A 118.3(4) . . ?
C13A C18A C19A 122.4(4) . . ?
O4A C19A O5A 124.0(4) . . ?
O4A C19A C18A 121.2(4) . . ?
O5A C19A C18A 114.8(5) . . ?
O5B O3B C16B 39.8(12) 3_575 . ?
O5B O3B H5BA 78.9 3_575 . ?
C16B O3B H5BA 117.1 . . ?
C15B O4B C14B 102(2) 3_575 3_575 ?
C15B O4B C19B 27(2) 3_575 . ?
C14B O4B C19B 91.8(13) 3_575 . ?
O3B O5B C16B 106(2) 3_575 3_575 ?
O3B O5B C19B 145(2) 3_575 . ?
C16B O5B C19B 40.0(10) 3_575 . ?
O3B O5B C15B 159(2) 3_575 3_575 ?
C16B O5B C15B 57.9(11) 3_575 3_575 ?
C19B O5B C15B 24.3(8) . 3_575 ?
O3B O5B H5BB 105.1 3_575 . ?
C16B O5B H5BB 144.1 3_575 . ?
C19B O5B H5BB 108.8 . . ?
C15B O5B H5BB 87.3 3_575 . ?
C17B C13B C14B 138(2) 3_575 . ?
C17B C13B C18B 27.7(15) 3_575 . ?
C14B C13B C18B 122.1(11) . . ?
C17B C13B C18B 55.4(14) 3_575 3_575 ?
C14B C13B C18B 86.2(10) . 3_575 ?
C18B C13B C18B 36.8(7) . 3_575 ?
C17B C13B C16B 29.4(14) 3_575 3_575 ?
C14B C13B C16B 167.4(12) . 3_575 ?
C18B C13B C16B 46.8(6) . 3_575 ?
C18B C13B C16B 81.8(7) 3_575 3_575 ?
C17B C13B H13B 99.5 3_575 . ?
C14B C13B H13B 117.9 . . ?
C18B C13B H13B 119.9 . . ?
C18B C13B H13B 154.8 3_575 . ?
C16B C13B H13B 73.6 3_575 . ?
O4B C14B C13B 143.9(15) 3_575 . ?
O4B C14B C15B 26.1(10) 3_575 . ?
C13B C14B C15B 120.4(13) . . ?
O4B C14B C19B 46.2(9) 3_575 3_575 ?
C13B C14B C19B 97.9(10) . 3_575 ?
C15B C14B C19B 24.6(8) . 3_575 ?
O4B C14B C17B 129.7(13) 3_575 3_575 ?
C13B C14B C17B 14.6(8) . 3_575 ?
C15B C14B C17B 107.6(11) . 3_575 ?
C19B C14B C17B 84.2(8) 3_575 3_575 ?
O4B C14B H14B 93.9 3_575 . ?
C13B C14B H14B 121.6 . . ?
C15B C14B H14B 117.8 . . ?
C19B C14B H14B 140.1 3_575 . ?
C17B C14B H14B 134.4 3_575 . ?
O4B C15B C19B 129(4) 3_575 3_575 ?
O4B C15B C14B 51.9(19) 3_575 . ?
C19B C15B C14B 101(2) 3_575 . ?
O4B C15B C16B 158(3) 3_575 . ?
C19B C15B C16B 28.1(17) 3_575 . ?
C14B C15B C16B 117.8(13) . . ?
O4B C15B O5B 148(3) 3_575 3_575 ?
C19B C15B O5B 49.0(15) 3_575 3_575 ?
C14B C15B O5B 149.0(14) . 3_575 ?
C16B C15B O5B 32.8(7) . 3_575 ?
O4B C15B C18B 117(2) 3_575 3_575 ?
C19B C15B C18B 34.8(16) 3_575 3_575 ?
C14B C15B C18B 71.2(9) . 3_575 ?
C16B C15B C18B 46.8(8) . 3_575 ?
O5B C15B C18B 78.3(9) 3_575 3_575 ?
O4B C15B H15B 71.9 3_575 . ?
C19B C15B H15B 129.0 3_575 . ?
C14B C15B H15B 121.9 . . ?
C16B C15B H15B 120.1 . . ?
O5B C15B H15B 87.5 3_575 . ?
C18B C15B H15B 163.8 3_575 . ?
C19B C16B O5B 96.9(17) 3_575 3_575 ?
C19B C16B O3B 130.8(17) 3_575 . ?
O5B C16B O3B 34.2(11) 3_575 . ?
C19B C16B C15B 23.4(15) 3_575 . ?
O5B C16B C15B 89.3(14) 3_575 . ?
O3B C16B C15B 122.2(12) . . ?
C19B C16B C17B 107.4(15) 3_575 . ?
O5B C16B C17B 149.7(16) 3_575 . ?
O3B C16B C17B 117.8(11) . . ?
C15B C16B C17B 120.0(12) . . ?
C19B C16B C18B 75.3(13) 3_575 3_575 ?
O5B C16B C18B 160.2(19) 3_575 3_575 ?
O3B C16B C18B 146.8(12) . 3_575 ?
C15B C16B C18B 89.8(10) . 3_575 ?
C17B C16B C18B 32.1(7) . 3_575 ?
C19B C16B C13B 116.8(15) 3_575 3_575 ?
O5B C16B C13B 134.7(15) 3_575 3_575 ?
O3B C16B C13B 104.4(9) . 3_575 ?
C15B C16B C13B 133.1(10) . 3_575 ?
C17B C16B C13B 15.2(8) . 3_575 ?
C18B C16B C13B 43.4(6) 3_575 3_575 ?
C13B C17B C18B 126(3) 3_575 3_575 ?
C13B C17B C18B 96.9(17) 3_575 . ?
C18B C17B C18B 46.0(13) 3_575 . ?
C13B C17B C16B 135(2) 3_575 . ?
C18B C17B C16B 78.1(14) 3_575 . ?
C18B C17B C16B 121.7(13) . . ?
C13B C17B C19B 147(2) 3_575 3_575 ?
C18B C17B C19B 52.4(11) 3_575 3_575 ?
C18B C17B C19B 96.7(11) . 3_575 ?
C16B C17B C19B 25.7(6) . 3_575 ?
C13B C17B C17B 108.7(19) 3_575 3_575 ?
C18B C17B C17B 29.1(9) 3_575 3_575 ?
C18B C17B C17B 16.9(5) . 3_575 ?
C16B C17B C17B 105.7(13) . 3_575 ?
C19B C17B C17B 80.4(10) 3_575 3_575 ?
C13B C17B C14B 27.3(14) 3_575 3_575 ?
C18B C17B C14B 111.9(15) 3_575 3_575 ?
C18B C17B C14B 72.6(8) . 3_575 ?
C16B C17B C14B 162.7(12) . 3_575 ?
C19B C17B C14B 159.9(11) 3_575 3_575 ?
C17B C17B C14B 87.1(9) 3_575 3_575 ?
C13B C17B H17B 28.4 3_575 . ?
C18B C17B H17B 154.6 3_575 . ?
C18B C17B H17B 118.3 . . ?
C16B C17B H17B 119.9 . . ?
C19B C17B H17B 143.6 3_575 . ?
C17B C17B H17B 133.3 3_575 . ?
C14B C17B H17B 46.2 3_575 . ?
C17B C18B C18B 97.6(18) 3_575 3_575 ?
C17B C18B C17B 134.0(13) 3_575 . ?
C18B C18B C17B 36.4(10) 3_575 . ?
C17B C18B C13B 26.1(14) 3_575 . ?
C18B C18B C13B 84.3(14) 3_575 . ?
C17B C18B C13B 117.8(10) . . ?
C17B C18B C16B 69.8(13) 3_575 3_575 ?
C18B C18B C16B 158(2) 3_575 3_575 ?
C17B C18B C16B 151.7(11) . 3_575 ?
C13B C18B C16B 89.9(9) . 3_575 ?
C17B C18B C19B 102.5(15) 3_575 . ?
C18B C18B C19B 152.7(18) 3_575 . ?
C17B C18B C19B 121.0(12) . . ?
C13B C18B C19B 121.1(10) . . ?
C16B C18B C19B 32.7(7) 3_575 . ?
C17B C18B C13B 148(2) 3_575 3_575 ?
C18B C18B C13B 58.9(12) 3_575 3_575 ?
C17B C18B C13B 27.7(8) . 3_575 ?
C13B C18B C13B 143.2(7) . 3_575 ?
C16B C18B C13B 124.1(10) 3_575 3_575 ?
C19B C18B C13B 95.2(10) . 3_575 ?
C17B C18B C15B 111.1(15) 3_575 3_575 ?
C18B C18B C15B 137.3(17) 3_575 3_575 ?
C17B C18B C15B 108.6(10) . 3_575 ?
C13B C18B C15B 133.3(9) . 3_575 ?
C16B C18B C15B 43.4(6) 3_575 3_575 ?
C19B C18B C15B 15.6(7) . 3_575 ?
C13B C18B C15B 81.5(7) 3_575 3_575 ?
C15B C19B C16B 129(3) 3_575 3_575 ?
C15B C19B O4B 24(2) 3_575 . ?
C16B C19B O4B 152(2) 3_575 . ?
C15B C19B O5B 107(2) 3_575 . ?
C16B C19B O5B 43.1(11) 3_575 . ?
O4B C19B O5B 123.1(14) . . ?
C15B C19B C18B 130(2) 3_575 . ?
C16B C19B C18B 72.0(13) 3_575 . ?
O4B C19B C18B 122.6(13) . . ?
O5B C19B C18B 113.0(12) . . ?
C15B C19B C14B 54.8(16) 3_575 3_575 ?
C16B C19B C14B 141.2(18) 3_575 3_575 ?
O4B C19B C14B 42.0(9) . 3_575 ?
O5B C19B C14B 160.7(14) . 3_575 ?
C18B C19B C14B 80.6(9) . 3_575 ?
C15B C19B C17B 140(3) 3_575 3_575 ?
C16B C19B C17B 47.0(11) 3_575 3_575 ?
O4B C19B C17B 143.7(13) . 3_575 ?
O5B C19B C17B 88.6(10) . 3_575 ?
C18B C19B C17B 25.1(7) . 3_575 ?
C14B C19B C17B 102.8(9) 3_575 3_575 ?
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full 22.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max 0.778
_refine_diff_density_min -0.603
_refine_diff_density_rms 0.083
data_c
_database_code_depnum_ccdc_archive 'CCDC 742683'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C14 H19 N5 O4, C7 H6 O3'
_chemical_formula_sum 'C21 H25 N5 O7'
_chemical_formula_weight 459.46
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_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 21/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 6.9162(3)
_cell_length_b 22.0035(9)
_cell_length_c 14.3569(5)
_cell_angle_alpha 90.00
_cell_angle_beta 90.319(2)
_cell_angle_gamma 90.00
_cell_volume 2184.81(15)
_cell_formula_units_Z 4
_cell_measurement_temperature 100.0(1)
_cell_measurement_reflns_used 9919
_cell_measurement_theta_min 2.84
_cell_measurement_theta_max 30.42
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.34
_exptl_crystal_size_mid 0.28
_exptl_crystal_size_min 0.10
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.397
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 968
_exptl_absorpt_coefficient_mu 0.107
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9651
_exptl_absorpt_correction_T_max 0.9898
_exptl_absorpt_process_details '(SADABS; Bruker, 2005)'
_exptl_special_details
; The crystal was placed in the cold stream of an Oxford Cyrosystems
Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating
at 100.0(1)K.
;
_diffrn_ambient_temperature 100.0(1)
_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
; Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 6612
_diffrn_reflns_av_R_equivalents 0.0000
_diffrn_reflns_av_sigmaI/netI 0.0445
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -31
_diffrn_reflns_limit_k_max 31
_diffrn_reflns_limit_l_min 0
_diffrn_reflns_limit_l_max 20
_diffrn_reflns_theta_min 2.33
_diffrn_reflns_theta_max 30.56
_reflns_number_total 6612
_reflns_number_gt 4752
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'APEX2 (Bruker, 2005)'
_computing_cell_refinement 'SAINT (Bruker, 2005)'
_computing_data_reduction SAINT
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement SHELXTL
_computing_molecular_graphics SHELXTL
_computing_publication_material
; SHELXTL (
Sheldrick, 2008), PLATON (
Spek, 2009)
;
_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 Rfactors
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^)+(0.1103P)^2^+2.7299P] 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 6612
_refine_ls_number_parameters 311
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1143
_refine_ls_R_factor_gt 0.0823
_refine_ls_wR_factor_ref 0.2302
_refine_ls_wR_factor_gt 0.2113
_refine_ls_goodness_of_fit_ref 1.063
_refine_ls_restrained_S_all 1.063
_refine_ls_shift/su_max <0.001
_refine_ls_shift/su_mean <0.001
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 0.2692(4) 0.60594(9) 0.28883(13) 0.0257(5) Uani 1 1 d . . .
O2 O 0.2477(4) 0.43118(9) 0.41422(12) 0.0230(5) Uani 1 1 d . . .
O3 O 0.3040(4) 0.18876(10) 0.10988(15) 0.0327(6) Uani 1 1 d . . .
O4 O -0.0078(4) 0.21726(12) 0.08484(18) 0.0311(6) Uani 1 1 d . . .
N1 N 0.2607(4) 0.55267(9) 0.15267(14) 0.0160(5) Uani 1 1 d . . .
H1A H 0.2612 0.5560 0.0930 0.019 Uiso 1 1 calc R . .
N2 N 0.2519(4) 0.48901(10) 0.28302(13) 0.0153(5) Uani 1 1 d . . .
H2A H 0.2577 0.5215 0.3161 0.018 Uiso 1 1 calc R . .
N3 N 0.2386(4) 0.44925(9) 0.13027(14) 0.0152(5) Uani 1 1 d . . .
N4 N 0.2239(4) 0.32542(11) 0.30327(15) 0.0215(5) Uani 1 1 d . . .
N5 N 0.2154(4) 0.34526(10) 0.10849(15) 0.0194(5) Uani 1 1 d . A .
C1 C 0.2709(5) 0.60630(12) 0.20344(18) 0.0170(5) Uani 1 1 d . . .
C2 C 0.2500(4) 0.49497(11) 0.18844(16) 0.0136(5) Uani 1 1 d . . .
C3 C 0.2292(4) 0.39207(12) 0.16935(17) 0.0150(5) Uani 1 1 d . . .
C4 C 0.2053(5) 0.29025(13) 0.14520(19) 0.0209(6) Uani 1 1 d . . .
C5 C 0.2095(6) 0.28045(13) 0.24253(19) 0.0248(7) Uani 1 1 d . A .
H5A H 0.2019 0.2408 0.2647 0.030 Uiso 1 1 calc R . .
C6 C 0.2320(4) 0.38163(12) 0.26618(17) 0.0160(5) Uani 1 1 d . . .
C7 C 0.2451(5) 0.43387(12) 0.32868(16) 0.0166(5) Uani 1 1 d . . .
C8 C 0.2808(5) 0.66450(12) 0.14631(18) 0.0192(6) Uani 1 1 d . . .
C9 C 0.2943(6) 0.71860(13) 0.2137(2) 0.0290(8) Uani 1 1 d . . .
H9A H 0.4091 0.7148 0.2512 0.043 Uiso 1 1 calc R . .
H9B H 0.1829 0.7190 0.2532 0.043 Uiso 1 1 calc R . .
H9C H 0.2995 0.7558 0.1787 0.043 Uiso 1 1 calc R . .
C10 C 0.4628(6) 0.66342(15) 0.0864(3) 0.0276(7) Uani 1 1 d . . .
H10A H 0.4535 0.6309 0.0420 0.041 Uiso 1 1 calc R . .
H10B H 0.5741 0.6572 0.1255 0.041 Uiso 1 1 calc R . .
H10C H 0.4750 0.7014 0.0540 0.041 Uiso 1 1 calc R . .
C11 C 0.0974(6) 0.66939(15) 0.0854(3) 0.0281(7) Uani 1 1 d . . .
H11A H 0.0962 0.6370 0.0406 0.042 Uiso 1 1 calc R . .
H11B H 0.0967 0.7078 0.0536 0.042 Uiso 1 1 calc R . .
H11C H -0.0149 0.6664 0.1241 0.042 Uiso 1 1 calc R . .
C12 C 0.1842(5) 0.23601(13) 0.0800(2) 0.0243(7) Uani 1 1 d . A .
H12A H 0.2164 0.2478 0.0161 0.029 Uiso 1 1 calc R . .
C13 C -0.0472(7) 0.16841(16) 0.0210(3) 0.0345(9) Uani 1 1 d . A .
H13A H -0.1844 0.1635 0.0142 0.052 Uiso 1 1 calc R . .
H13B H 0.0084 0.1315 0.0447 0.052 Uiso 1 1 calc R . .
H13C H 0.0082 0.1777 -0.0385 0.052 Uiso 1 1 calc R . .
C14A C 0.4717(6) 0.18057(18) 0.0543(3) 0.0300(11) Uani 0.909(11) 1 d P A 1
H14A H 0.4345 0.1778 -0.0101 0.045 Uiso 0.909(11) 1 calc PR A 1
H14B H 0.5366 0.1439 0.0727 0.045 Uiso 0.909(11) 1 calc PR A 1
H14C H 0.5572 0.2145 0.0628 0.045 Uiso 0.909(11) 1 calc PR A 1
C14B C 0.478(5) 0.2184(15) 0.086(2) 0.015(8) Uiso 0.091(11) 1 d P A 2
H14D H 0.4767 0.2591 0.1098 0.022 Uiso 0.091(11) 1 calc PR A 2
H14E H 0.4905 0.2194 0.0194 0.022 Uiso 0.091(11) 1 calc PR A 2
H14F H 0.5856 0.1966 0.1125 0.022 Uiso 0.091(11) 1 calc PR A 2
O5 O 0.2727(4) 0.53415(9) 0.51673(13) 0.0282(6) Uani 1 1 d . . .
H5 H 0.2566 0.5016 0.4900 0.042 Uiso 1 1 calc R . .
O6 O 0.2622(4) 0.55163(9) 0.95727(13) 0.0290(6) Uani 1 1 d . . .
O7 O 0.2195(4) 0.45181(9) 0.93743(13) 0.0268(5) Uani 1 1 d . . .
H7A H 0.2195 0.4521 0.9945 0.040 Uiso 1 1 calc R . .
C15 C 0.2647(5) 0.57024(12) 0.76309(17) 0.0185(6) Uani 1 1 d . . .
H15A H 0.2705 0.6045 0.8009 0.022 Uiso 1 1 calc R . .
C16 C 0.2716(5) 0.57676(12) 0.66689(17) 0.0201(6) Uani 1 1 d . . .
H16A H 0.2817 0.6152 0.6405 0.024 Uiso 1 1 calc R . .
C17 C 0.2634(5) 0.52551(12) 0.61001(17) 0.0188(6) Uani 1 1 d . . .
C18 C 0.2472(5) 0.46771(12) 0.64946(16) 0.0192(6) Uani 1 1 d . . .
H18A H 0.2422 0.4335 0.6116 0.023 Uiso 1 1 calc R . .
C19 C 0.2387(5) 0.46169(12) 0.74569(17) 0.0182(5) Uani 1 1 d . . .
H19A H 0.2258 0.4233 0.7719 0.022 Uiso 1 1 calc R . .
C20 C 0.2491(5) 0.51268(11) 0.80343(15) 0.0149(5) Uani 1 1 d . . .
C21 C 0.2446(5) 0.50756(12) 0.90618(16) 0.0164(5) Uani 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 0.0452(15) 0.0196(9) 0.0122(8) -0.0024(7) -0.0016(10) -0.0017(11)
O2 0.0390(14) 0.0230(9) 0.0070(7) 0.0012(6) -0.0007(9) -0.0027(10)
O3 0.0533(18) 0.0234(11) 0.0214(10) 0.0040(8) 0.0020(11) 0.0101(11)
O4 0.0366(15) 0.0303(12) 0.0264(12) -0.0085(10) 0.0027(10) -0.0048(11)
N1 0.0266(14) 0.0147(9) 0.0065(8) 0.0006(7) -0.0029(9) -0.0002(10)
N2 0.0239(13) 0.0161(9) 0.0060(8) -0.0001(7) -0.0034(9) -0.0011(10)
N3 0.0214(12) 0.0146(9) 0.0095(8) 0.0008(7) -0.0020(9) 0.0013(10)
N4 0.0323(15) 0.0194(10) 0.0127(9) 0.0040(8) 0.0011(10) -0.0007(11)
N5 0.0292(15) 0.0161(10) 0.0130(9) -0.0010(8) -0.0007(10) 0.0007(11)
C1 0.0214(15) 0.0155(11) 0.0142(10) -0.0015(8) -0.0015(11) -0.0011(12)
C2 0.0146(13) 0.0188(11) 0.0074(9) 0.0000(8) -0.0034(10) 0.0001(11)
C3 0.0164(13) 0.0172(11) 0.0114(10) -0.0002(8) -0.0028(10) 0.0003(11)
C4 0.0321(17) 0.0175(12) 0.0132(11) -0.0007(9) -0.0001(12) -0.0014(13)
C5 0.042(2) 0.0181(12) 0.0147(12) 0.0036(9) 0.0005(13) -0.0026(14)
C6 0.0192(14) 0.0183(11) 0.0104(10) 0.0009(8) -0.0001(10) 0.0007(11)
C7 0.0219(15) 0.0185(11) 0.0093(10) 0.0007(8) -0.0025(10) -0.0026(12)
C8 0.0274(16) 0.0145(11) 0.0156(11) 0.0005(9) -0.0029(12) 0.0007(12)
C9 0.048(2) 0.0162(12) 0.0227(14) -0.0026(10) -0.0023(15) -0.0017(14)
C10 0.0337(19) 0.0210(14) 0.0282(16) 0.0030(13) 0.0072(14) -0.0029(14)
C11 0.0326(19) 0.0206(15) 0.0308(17) 0.0023(13) -0.0121(14) 0.0041(14)
C12 0.039(2) 0.0172(13) 0.0161(12) 0.0006(10) 0.0025(13) 0.0012(13)
C13 0.046(2) 0.0270(17) 0.0310(18) -0.0079(14) 0.0036(16) -0.0050(16)
C14A 0.031(2) 0.026(2) 0.032(2) 0.0043(16) -0.0025(16) 0.0056(16)
O5 0.0556(17) 0.0208(9) 0.0082(8) 0.0000(7) -0.0008(10) 0.0019(11)
O6 0.0565(17) 0.0211(9) 0.0094(8) -0.0017(7) -0.0004(11) -0.0021(12)
O7 0.0529(16) 0.0190(9) 0.0085(8) 0.0018(7) 0.0006(10) -0.0039(11)
C15 0.0276(16) 0.0167(11) 0.0111(10) -0.0016(8) 0.0011(11) 0.0025(12)
C16 0.0338(17) 0.0161(11) 0.0105(10) 0.0020(8) -0.0012(12) 0.0012(13)
C17 0.0275(16) 0.0202(12) 0.0087(10) 0.0015(8) -0.0033(11) 0.0029(13)
C18 0.0308(17) 0.0190(12) 0.0078(10) -0.0017(8) -0.0018(11) 0.0030(13)
C19 0.0259(15) 0.0170(11) 0.0118(10) 0.0013(8) -0.0036(11) 0.0013(12)
C20 0.0190(14) 0.0199(11) 0.0057(9) -0.0003(8) -0.0030(10) 0.0021(12)
C21 0.0218(14) 0.0195(11) 0.0080(9) 0.0006(8) 0.0001(10) 0.0028(12)
_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 C1 1.226(3) . ?
O2 C7 1.230(3) . ?
O3 C12 1.396(4) . ?
O3 C14B 1.41(3) . ?
O3 C14A 1.423(5) . ?
O4 C12 1.392(4) . ?
O4 C13 1.437(4) . ?
N1 C2 1.372(3) . ?
N1 C1 1.389(3) . ?
N1 H1A 0.8600 . ?
N2 C2 1.364(3) . ?
N2 C7 1.380(3) . ?
N2 H2A 0.8600 . ?
N3 C2 1.310(3) . ?
N3 C3 1.379(3) . ?
N4 C5 1.322(4) . ?
N4 C6 1.348(3) . ?
N5 C4 1.322(3) . ?
N5 C3 1.354(3) . ?
C1 C8 1.523(4) . ?
C3 C6 1.409(3) . ?
C4 C5 1.414(4) . ?
C4 C12 1.523(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.461(3) . ?
C8 C10 1.529(5) . ?
C8 C9 1.536(4) . ?
C8 C11 1.540(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
C14B H14D 0.9600 . ?
C14B H14E 0.9600 . ?
C14B H14F 0.9600 . ?
O5 C17 1.355(3) . ?
O5 H5 0.8200 . ?
O6 C21 1.222(3) . ?
O7 C21 1.318(3) . ?
O7 H7A 0.8200 . ?
C15 C16 1.390(3) . ?
C15 C20 1.397(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.393(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.397(4) . ?
C18 C19 1.389(3) . ?
C18 H18A 0.9300 . ?
C19 C20 1.397(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.480(3) . ?
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
C12 O3 C14B 95.0(13) . . ?
C12 O3 C14A 114.0(3) . . ?
C12 O4 C13 111.6(3) . . ?
C2 N1 C1 126.4(2) . . ?
C2 N1 H1A 116.8 . . ?
C1 N1 H1A 116.8 . . ?
C2 N2 C7 123.9(2) . . ?
C2 N2 H2A 118.1 . . ?
C7 N2 H2A 118.1 . . ?
C2 N3 C3 116.4(2) . . ?
C5 N4 C6 115.4(2) . . ?
C4 N5 C3 116.3(2) . . ?
O1 C1 N1 121.2(2) . . ?
O1 C1 C8 123.0(2) . . ?
N1 C1 C8 115.7(2) . . ?
N3 C2 N2 124.1(2) . . ?
N3 C2 N1 118.4(2) . . ?
N2 C2 N1 117.5(2) . . ?
N5 C3 N3 115.8(2) . . ?
N5 C3 C6 120.9(2) . . ?
N3 C3 C6 123.3(2) . . ?
N5 C4 C5 122.2(2) . . ?
N5 C4 C12 118.5(2) . . ?
C5 C4 C12 119.3(2) . . ?
N4 C5 C4 122.6(3) . . ?
N4 C5 H5A 118.7 . . ?
C4 C5 H5A 118.7 . . ?
N4 C6 C3 122.6(2) . . ?
N4 C6 C7 118.8(2) . . ?
C3 C6 C7 118.6(2) . . ?
O2 C7 N2 121.1(2) . . ?
O2 C7 C6 125.2(2) . . ?
N2 C7 C6 113.7(2) . . ?
C1 C8 C10 109.2(2) . . ?
C1 C8 C9 108.4(2) . . ?
C10 C8 C9 108.6(3) . . ?
C1 C8 C11 109.0(3) . . ?
C10 C8 C11 111.1(2) . . ?
C9 C8 C11 110.5(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 O3 109.2(3) . . ?
O4 C12 C4 106.8(3) . . ?
O3 C12 C4 109.9(3) . . ?
O4 C12 H12A 110.3 . . ?
O3 C12 H12A 110.3 . . ?
C4 C12 H12A 110.3 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14A H14A 109.5 . . ?
O3 C14A H14B 109.5 . . ?
O3 C14A H14C 109.5 . . ?
O3 C14B H14D 109.5 . . ?
O3 C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
O3 C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C17 O5 H5 109.5 . . ?
C21 O7 H7A 109.5 . . ?
C16 C15 C20 120.6(2) . . ?
C16 C15 H15A 119.7 . . ?
C20 C15 H15A 119.7 . . ?
C15 C16 C17 119.8(2) . . ?
C15 C16 H16A 120.1 . . ?
C17 C16 H16A 120.1 . . ?
O5 C17 C16 117.6(2) . . ?
O5 C17 C18 122.2(2) . . ?
C16 C17 C18 120.1(2) . . ?
C19 C18 C17 119.6(2) . . ?
C19 C18 H18A 120.2 . . ?
C17 C18 H18A 120.2 . . ?
C18 C19 C20 120.7(2) . . ?
C18 C19 H19A 119.6 . . ?
C20 C19 H19A 119.6 . . ?
C19 C20 C15 119.1(2) . . ?
C19 C20 C21 121.9(2) . . ?
C15 C20 C21 119.0(2) . . ?
O6 C21 O7 123.2(2) . . ?
O6 C21 C20 122.4(2) . . ?
O7 C21 C20 114.4(2) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 O1 -0.7(5) . . . . ?
C2 N1 C1 C8 -179.8(3) . . . . ?
C3 N3 C2 N2 -0.4(5) . . . . ?
C3 N3 C2 N1 179.7(3) . . . . ?
C7 N2 C2 N3 1.1(5) . . . . ?
C7 N2 C2 N1 -179.0(3) . . . . ?
C1 N1 C2 N3 179.1(3) . . . . ?
C1 N1 C2 N2 -0.9(5) . . . . ?
C4 N5 C3 N3 -179.6(3) . . . . ?
C4 N5 C3 C6 -0.1(5) . . . . ?
C2 N3 C3 N5 179.4(3) . . . . ?
C2 N3 C3 C6 -0.2(5) . . . . ?
C3 N5 C4 C5 -0.3(5) . . . . ?
C3 N5 C4 C12 178.4(3) . . . . ?
C6 N4 C5 C4 0.7(5) . . . . ?
N5 C4 C5 N4 0.0(6) . . . . ?
C12 C4 C5 N4 -178.7(3) . . . . ?
C5 N4 C6 C3 -1.2(5) . . . . ?
C5 N4 C6 C7 179.1(3) . . . . ?
N5 C3 C6 N4 0.9(5) . . . . ?
N3 C3 C6 N4 -179.6(3) . . . . ?
N5 C3 C6 C7 -179.4(3) . . . . ?
N3 C3 C6 C7 0.2(5) . . . . ?
C2 N2 C7 O2 179.8(3) . . . . ?
C2 N2 C7 C6 -1.0(4) . . . . ?
N4 C6 C7 O2 -0.7(5) . . . . ?
C3 C6 C7 O2 179.6(3) . . . . ?
N4 C6 C7 N2 -179.8(3) . . . . ?
C3 C6 C7 N2 0.4(4) . . . . ?
O1 C1 C8 C10 120.0(3) . . . . ?
N1 C1 C8 C10 -61.0(4) . . . . ?
O1 C1 C8 C9 1.8(5) . . . . ?
N1 C1 C8 C9 -179.2(3) . . . . ?
O1 C1 C8 C11 -118.5(4) . . . . ?
N1 C1 C8 C11 60.5(4) . . . . ?
C13 O4 C12 O3 -64.9(3) . . . . ?
C13 O4 C12 C4 176.2(3) . . . . ?
C14B O3 C12 O4 173.1(13) . . . . ?
C14A O3 C12 O4 137.6(3) . . . . ?
C14B O3 C12 C4 -70.0(13) . . . . ?
C14A O3 C12 C4 -105.5(3) . . . . ?
N5 C4 C12 O4 -104.1(3) . . . . ?
C5 C4 C12 O4 74.6(4) . . . . ?
N5 C4 C12 O3 137.5(3) . . . . ?
C5 C4 C12 O3 -43.7(4) . . . . ?
C20 C15 C16 C17 -0.2(5) . . . . ?
C15 C16 C17 O5 -179.3(3) . . . . ?
C15 C16 C17 C18 0.4(5) . . . . ?
O5 C17 C18 C19 179.9(3) . . . . ?
C16 C17 C18 C19 0.2(5) . . . . ?
C17 C18 C19 C20 -1.0(5) . . . . ?
C18 C19 C20 C15 1.2(5) . . . . ?
C18 C19 C20 C21 -178.6(3) . . . . ?
C16 C15 C20 C19 -0.6(5) . . . . ?
C16 C15 C20 C21 179.2(3) . . . . ?
C19 C20 C21 O6 176.7(3) . . . . ?
C15 C20 C21 O6 -3.1(5) . . . . ?
C19 C20 C21 O7 -3.5(5) . . . . ?
C15 C20 C21 O7 176.6(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full 30.56
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max 0.655
_refine_diff_density_min -0.460
_refine_diff_density_rms 0.094
data_fs57_0m
_database_code_depnum_ccdc_archive 'CCDC 742684'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C14 H19 N5 O4, C7 H5 N O4'
_chemical_formula_sum 'C21 H24 N6 O8'
_chemical_formula_weight 488.46
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_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.4059(3)
_cell_length_b 11.7146(4)
_cell_length_c 11.8703(4)
_cell_angle_alpha 92.873(2)
_cell_angle_beta 92.647(2)
_cell_angle_gamma 104.299(2)
_cell_volume 1129.18(7)
_cell_formula_units_Z 2
_cell_measurement_temperature 100.0(1)
_cell_measurement_reflns_used 9945
_cell_measurement_theta_min 2.41
_cell_measurement_theta_max 39.79
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.77
_exptl_crystal_size_mid 0.40
_exptl_crystal_size_min 0.33
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.437
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 512
_exptl_absorpt_coefficient_mu 0.112
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9188
_exptl_absorpt_correction_T_max 0.9640
_exptl_absorpt_process_details '(SADABS; Bruker, 2005)'
_exptl_special_details
; The crystal was placed in the cold stream of an Oxford Cyrosystems
Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating
at 100.0(1)K.
;
_diffrn_ambient_temperature 100.0(1)
_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
; Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 30598
_diffrn_reflns_av_R_equivalents 0.0275
_diffrn_reflns_av_sigmaI/netI 0.0220
_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 -16
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_theta_min 1.72
_diffrn_reflns_theta_max 29.00
_reflns_number_total 5953
_reflns_number_gt 4882
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'APEX2 (Bruker, 2005)'
_computing_cell_refinement 'SAINT (Bruker, 2005)'
_computing_data_reduction SAINT
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement SHELXTL
_computing_molecular_graphics SHELXTL
_computing_publication_material
; SHELXTL (
Sheldrick, 2008), PLATON (
Spek, 2009)
;
_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 Rfactors
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^)+(0.0600P)^2^+0.3825P] 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 5953
_refine_ls_number_parameters 333
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0509
_refine_ls_R_factor_gt 0.0397
_refine_ls_wR_factor_ref 0.1195
_refine_ls_wR_factor_gt 0.1068
_refine_ls_goodness_of_fit_ref 1.058
_refine_ls_restrained_S_all 1.058
_refine_ls_shift/su_max <0.001
_refine_ls_shift/su_mean <0.001
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 -0.00718(11) 0.56895(8) 0.32987(8) 0.0263(2) Uani 1 1 d . . .
O2 O 0.31189(11) 0.82438(8) 0.56910(8) 0.0273(2) Uani 1 1 d . . .
O3 O 0.30648(11) 1.40875(7) 0.51495(7) 0.02408(19) Uani 1 1 d . . .
O4 O 0.32246(11) 1.36115(8) 0.32667(8) 0.0267(2) Uani 1 1 d . . .
N1 N 0.11999(12) 0.78412(9) 0.42202(9) 0.0205(2) Uani 1 1 d . . .
N2 N 0.33934(12) 1.07061(9) 0.55009(9) 0.0216(2) Uani 1 1 d . . .
N3 N 0.12747(12) 1.12545(9) 0.38225(8) 0.0198(2) Uani 1 1 d . . .
N4 N 0.02615(12) 0.92866(9) 0.32528(8) 0.0195(2) Uani 1 1 d . . .
N5 N -0.07586(13) 0.73308(9) 0.26852(9) 0.0219(2) Uani 1 1 d . . .
C1 C 0.23163(14) 0.86157(10) 0.49893(10) 0.0201(2) Uani 1 1 d . . .
C2 C 0.23592(13) 0.98610(10) 0.48266(10) 0.0184(2) Uani 1 1 d . . .
C3 C 0.33763(14) 1.18117(10) 0.53252(10) 0.0217(2) Uani 1 1 d . . .
H3A H 0.4087 1.2424 0.5765 0.026 Uiso 1 1 calc R . .
C4 C 0.23041(14) 1.20819(10) 0.44861(10) 0.0196(2) Uani 1 1 d . . .
C5 C 0.13115(13) 1.01278(10) 0.39767(10) 0.0180(2) Uani 1 1 d . . .
C6 C 0.02644(14) 0.81888(10) 0.34016(10) 0.0187(2) Uani 1 1 d . . .
C7 C -0.09086(14) 0.61211(10) 0.26576(10) 0.0215(2) Uani 1 1 d . . .
C8 C -0.21428(15) 0.54019(11) 0.17463(11) 0.0233(2) Uani 1 1 d . . .
C9 C -0.15498(18) 0.58002(12) 0.05874(11) 0.0306(3) Uani 1 1 d . . .
H9A H -0.0423 0.5774 0.0539 0.046 Uiso 1 1 calc R . .
H9B H -0.1642 0.6592 0.0502 0.046 Uiso 1 1 calc R . .
H9C H -0.2215 0.5283 -0.0001 0.046 Uiso 1 1 calc R . .
C10 C -0.22028(18) 0.40900(11) 0.18267(12) 0.0313(3) Uani 1 1 d . . .
H10A H -0.2489 0.3859 0.2570 0.047 Uiso 1 1 calc R . .
H10B H -0.1145 0.3961 0.1682 0.047 Uiso 1 1 calc R . .
H10C H -0.3013 0.3629 0.1278 0.047 Uiso 1 1 calc R . .
C11 C -0.38566(16) 0.56014(12) 0.19026(12) 0.0287(3) Uani 1 1 d . . .
H11A H -0.4230 0.5328 0.2617 0.043 Uiso 1 1 calc R . .
H11B H -0.4609 0.5173 0.1305 0.043 Uiso 1 1 calc R . .
H11C H -0.3805 0.6428 0.1884 0.043 Uiso 1 1 calc R . .
C12 C 0.23135(15) 1.33385(10) 0.42343(10) 0.0217(2) Uani 1 1 d . . .
H12A H 0.1186 1.3409 0.4088 0.026 Uiso 1 1 calc R . .
C13 C 0.29889(16) 1.52882(11) 0.50212(12) 0.0267(3) Uani 1 1 d . . .
H13A H 0.3681 1.5794 0.5605 0.040 Uiso 1 1 calc R . .
H13B H 0.1876 1.5346 0.5078 0.040 Uiso 1 1 calc R . .
H13C H 0.3359 1.5525 0.4296 0.040 Uiso 1 1 calc R . .
C14 C 0.22310(19) 1.35712(13) 0.22552(12) 0.0340(3) Uani 1 1 d . . .
H14A H 0.2921 1.3721 0.1629 0.051 Uiso 1 1 calc R . .
H14B H 0.1618 1.4160 0.2322 0.051 Uiso 1 1 calc R . .
H14C H 0.1484 1.2805 0.2132 0.051 Uiso 1 1 calc R . .
O5 O 0.10986(12) 0.97459(8) -0.14357(8) 0.0287(2) Uani 1 1 d . . .
O6 O 0.25630(12) 1.16217(8) -0.11488(9) 0.0339(2) Uani 1 1 d . . .
O7 O 0.27525(15) 0.68637(9) 0.09419(9) 0.0425(3) Uani 1 1 d . . .
O8 O 0.37318(12) 0.74220(8) 0.26500(8) 0.0301(2) Uani 1 1 d . . .
N6 N 0.33050(13) 0.76286(9) 0.16963(9) 0.0242(2) Uani 1 1 d . . .
C15 C 0.27084(14) 0.90951(11) 0.04427(10) 0.0207(2) Uani 1 1 d . . .
H15A H 0.2092 0.8485 -0.0047 0.025 Uiso 1 1 calc R . .
C16 C 0.34670(14) 0.88684(10) 0.14421(10) 0.0203(2) Uani 1 1 d . . .
C17 C 0.43819(14) 0.97463(11) 0.22063(10) 0.0225(2) Uani 1 1 d . . .
H17A H 0.4864 0.9559 0.2870 0.027 Uiso 1 1 calc R . .
C18 C 0.45578(15) 1.09141(11) 0.19512(11) 0.0250(3) Uani 1 1 d . . .
H18A H 0.5160 1.1522 0.2449 0.030 Uiso 1 1 calc R . .
C19 C 0.38323(15) 1.11713(11) 0.09503(11) 0.0249(3) Uani 1 1 d . . .
H19A H 0.3966 1.1954 0.0778 0.030 Uiso 1 1 calc R . .
C20 C 0.29075(14) 1.02702(11) 0.02030(10) 0.0215(2) Uani 1 1 d . . .
C21 C 0.21711(15) 1.06104(11) -0.08608(11) 0.0233(2) Uani 1 1 d . . .
H1O5 H 0.072(3) 1.0042(19) -0.1995(19) 0.058(6) Uiso 1 1 d . . .
H1N1 H 0.113(2) 0.7073(16) 0.4226(15) 0.037(4) Uiso 1 1 d . . .
H1N5 H -0.135(2) 0.7654(16) 0.2228(17) 0.046(5) 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 0.0283(4) 0.0241(4) 0.0272(5) 0.0014(4) -0.0084(4) 0.0095(3)
O2 0.0314(5) 0.0264(4) 0.0249(5) 0.0038(4) -0.0113(4) 0.0106(4)
O3 0.0310(4) 0.0197(4) 0.0215(4) 0.0022(3) -0.0065(3) 0.0075(3)
O4 0.0281(4) 0.0303(5) 0.0209(5) 0.0075(4) -0.0019(4) 0.0054(4)
N1 0.0230(5) 0.0202(5) 0.0192(5) 0.0013(4) -0.0058(4) 0.0081(4)
N2 0.0218(5) 0.0240(5) 0.0188(5) 0.0022(4) -0.0054(4) 0.0061(4)
N3 0.0204(4) 0.0212(5) 0.0179(5) 0.0034(4) -0.0029(4) 0.0054(4)
N4 0.0194(4) 0.0220(5) 0.0167(5) 0.0016(4) -0.0048(4) 0.0056(4)
N5 0.0244(5) 0.0216(5) 0.0196(5) 0.0002(4) -0.0082(4) 0.0076(4)
C1 0.0203(5) 0.0239(5) 0.0167(6) 0.0010(4) -0.0035(4) 0.0075(4)
C2 0.0181(5) 0.0224(5) 0.0153(5) 0.0023(4) -0.0022(4) 0.0064(4)
C3 0.0216(5) 0.0232(6) 0.0190(6) 0.0023(4) -0.0056(4) 0.0039(4)
C4 0.0195(5) 0.0223(5) 0.0171(5) 0.0039(4) -0.0011(4) 0.0052(4)
C5 0.0169(5) 0.0228(5) 0.0147(5) 0.0030(4) -0.0015(4) 0.0059(4)
C6 0.0182(5) 0.0237(5) 0.0151(5) 0.0011(4) -0.0023(4) 0.0076(4)
C7 0.0226(5) 0.0225(5) 0.0195(6) 0.0007(4) -0.0018(4) 0.0066(4)
C8 0.0268(6) 0.0224(6) 0.0196(6) -0.0008(4) -0.0060(5) 0.0056(4)
C9 0.0410(7) 0.0279(6) 0.0211(6) -0.0014(5) -0.0017(5) 0.0066(5)
C10 0.0403(7) 0.0229(6) 0.0285(7) -0.0014(5) -0.0086(6) 0.0063(5)
C11 0.0245(6) 0.0307(6) 0.0286(7) 0.0019(5) -0.0065(5) 0.0039(5)
C12 0.0228(5) 0.0226(5) 0.0190(6) 0.0041(4) -0.0044(4) 0.0050(4)
C13 0.0312(6) 0.0203(6) 0.0284(7) 0.0053(5) -0.0054(5) 0.0068(5)
C14 0.0411(8) 0.0384(7) 0.0204(7) 0.0047(5) -0.0061(6) 0.0069(6)
O5 0.0319(5) 0.0278(5) 0.0238(5) 0.0038(4) -0.0144(4) 0.0048(4)
O6 0.0401(5) 0.0266(5) 0.0325(5) 0.0057(4) -0.0181(4) 0.0065(4)
O7 0.0670(8) 0.0258(5) 0.0312(6) -0.0017(4) -0.0189(5) 0.0098(5)
O8 0.0351(5) 0.0354(5) 0.0211(5) 0.0087(4) -0.0039(4) 0.0112(4)
N6 0.0251(5) 0.0274(5) 0.0204(5) 0.0032(4) -0.0033(4) 0.0079(4)
C15 0.0192(5) 0.0257(6) 0.0170(6) -0.0004(4) -0.0042(4) 0.0065(4)
C16 0.0202(5) 0.0245(6) 0.0175(6) 0.0030(4) -0.0014(4) 0.0084(4)
C17 0.0214(5) 0.0321(6) 0.0151(5) 0.0022(5) -0.0029(4) 0.0093(5)
C18 0.0265(6) 0.0282(6) 0.0188(6) -0.0022(5) -0.0070(5) 0.0063(5)
C19 0.0277(6) 0.0249(6) 0.0223(6) 0.0005(5) -0.0067(5) 0.0085(5)
C20 0.0203(5) 0.0271(6) 0.0181(6) 0.0021(4) -0.0047(4) 0.0090(4)
C21 0.0236(5) 0.0261(6) 0.0204(6) 0.0016(5) -0.0069(4) 0.0083(4)
_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 C7 1.2224(14) . ?
O2 C1 1.2118(13) . ?
O3 C12 1.3842(15) . ?
O3 C13 1.4390(14) . ?
O4 C12 1.4160(15) . ?
O4 C14 1.4226(15) . ?
N1 C6 1.3622(13) . ?
N1 C1 1.3981(15) . ?
N1 H1N1 0.887(18) . ?
N2 C3 1.3255(15) . ?
N2 C2 1.3445(15) . ?
N3 C4 1.3247(15) . ?
N3 C5 1.3492(14) . ?
N4 C6 1.3074(15) . ?
N4 C5 1.3798(15) . ?
N5 C6 1.3758(15) . ?
N5 C7 1.3900(15) . ?
N5 H1N5 0.879(19) . ?
C1 C2 1.4730(15) . ?
C2 C5 1.4059(14) . ?
C3 C4 1.4122(15) . ?
C3 H3A 0.9300 . ?
C4 C12 1.5149(15) . ?
C7 C8 1.5262(16) . ?
C8 C10 1.5331(17) . ?
C8 C11 1.5333(18) . ?
C8 C9 1.5399(19) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O5 C21 1.3142(15) . ?
O5 H1O5 0.85(2) . ?
O6 C21 1.2196(15) . ?
O7 N6 1.2232(15) . ?
O8 N6 1.2255(13) . ?
N6 C16 1.4728(15) . ?
C15 C16 1.3891(15) . ?
C15 C20 1.3906(16) . ?
C15 H15A 0.9300 . ?
C16 C17 1.3869(17) . ?
C17 C18 1.3896(17) . ?
C17 H17A 0.9300 . ?
C18 C19 1.3907(16) . ?
C18 H18A 0.9300 . ?
C19 C20 1.3938(17) . ?
C19 H19A 0.9300 . ?
C20 C21 1.4955(15) . ?
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
C12 O3 C13 112.45(9) . . ?
C12 O4 C14 113.83(10) . . ?
C6 N1 C1 124.29(10) . . ?
C6 N1 H1N1 116.5(11) . . ?
C1 N1 H1N1 119.1(11) . . ?
C3 N2 C2 116.51(10) . . ?
C4 N3 C5 116.55(9) . . ?
C6 N4 C5 116.12(9) . . ?
C6 N5 C7 127.35(10) . . ?
C6 N5 H1N5 110.0(12) . . ?
C7 N5 H1N5 122.7(13) . . ?
O2 C1 N1 120.73(11) . . ?
O2 C1 C2 126.90(11) . . ?
N1 C1 C2 112.37(9) . . ?
N2 C2 C5 122.12(10) . . ?
N2 C2 C1 118.88(9) . . ?
C5 C2 C1 119.01(10) . . ?
N2 C3 C4 121.52(11) . . ?
N2 C3 H3A 119.2 . . ?
C4 C3 H3A 119.2 . . ?
N3 C4 C3 122.35(10) . . ?
N3 C4 C12 115.05(9) . . ?
C3 C4 C12 122.51(10) . . ?
N3 C5 N4 115.34(9) . . ?
N3 C5 C2 120.91(10) . . ?
N4 C5 C2 123.74(10) . . ?
N4 C6 N1 124.43(11) . . ?
N4 C6 N5 117.44(10) . . ?
N1 C6 N5 118.12(10) . . ?
O1 C7 N5 121.67(11) . . ?
O1 C7 C8 123.66(11) . . ?
N5 C7 C8 114.64(10) . . ?
C7 C8 C10 109.01(10) . . ?
C7 C8 C11 110.37(10) . . ?
C10 C8 C11 109.70(11) . . ?
C7 C8 C9 108.03(10) . . ?
C10 C8 C9 109.60(11) . . ?
C11 C8 C9 110.09(10) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 O4 110.02(10) . . ?
O3 C12 C4 108.97(9) . . ?
O4 C12 C4 107.41(10) . . ?
O3 C12 H12A 110.1 . . ?
O4 C12 H12A 110.1 . . ?
C4 C12 H12A 110.1 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C21 O5 H1O5 107.0(14) . . ?
O7 N6 O8 123.75(11) . . ?
O7 N6 C16 118.04(10) . . ?
O8 N6 C16 118.21(10) . . ?
C16 C15 C20 117.39(11) . . ?
C16 C15 H15A 121.3 . . ?
C20 C15 H15A 121.3 . . ?
C17 C16 C15 123.52(11) . . ?
C17 C16 N6 118.31(10) . . ?
C15 C16 N6 118.17(11) . . ?
C16 C17 C18 118.06(10) . . ?
C16 C17 H17A 121.0 . . ?
C18 C17 H17A 121.0 . . ?
C17 C18 C19 119.88(11) . . ?
C17 C18 H18A 120.1 . . ?
C19 C18 H18A 120.1 . . ?
C18 C19 C20 120.77(11) . . ?
C18 C19 H19A 119.6 . . ?
C20 C19 H19A 119.6 . . ?
C15 C20 C19 120.37(10) . . ?
C15 C20 C21 121.70(11) . . ?
C19 C20 C21 117.92(11) . . ?
O6 C21 O5 124.08(11) . . ?
O6 C21 C20 121.02(11) . . ?
O5 C21 C20 114.90(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
C6 N1 C1 O2 -179.41(12) . . . . ?
C6 N1 C1 C2 0.67(17) . . . . ?
C3 N2 C2 C5 0.07(18) . . . . ?
C3 N2 C2 C1 -179.53(10) . . . . ?
O2 C1 C2 N2 0.79(19) . . . . ?
N1 C1 C2 N2 -179.29(10) . . . . ?
O2 C1 C2 C5 -178.82(12) . . . . ?
N1 C1 C2 C5 1.09(16) . . . . ?
C2 N2 C3 C4 1.11(18) . . . . ?
C5 N3 C4 C3 -0.81(17) . . . . ?
C5 N3 C4 C12 175.89(10) . . . . ?
N2 C3 C4 N3 -0.78(19) . . . . ?
N2 C3 C4 C12 -177.24(11) . . . . ?
C4 N3 C5 N4 -178.20(10) . . . . ?
C4 N3 C5 C2 1.97(17) . . . . ?
C6 N4 C5 N3 -179.04(10) . . . . ?
C6 N4 C5 C2 0.79(17) . . . . ?
N2 C2 C5 N3 -1.69(18) . . . . ?
C1 C2 C5 N3 177.91(10) . . . . ?
N2 C2 C5 N4 178.49(11) . . . . ?
C1 C2 C5 N4 -1.91(18) . . . . ?
C5 N4 C6 N1 1.12(18) . . . . ?
C5 N4 C6 N5 -179.39(10) . . . . ?
C1 N1 C6 N4 -1.92(19) . . . . ?
C1 N1 C6 N5 178.59(11) . . . . ?
C7 N5 C6 N4 177.23(11) . . . . ?
C7 N5 C6 N1 -3.25(19) . . . . ?
C6 N5 C7 O1 -1.2(2) . . . . ?
C6 N5 C7 C8 -179.17(11) . . . . ?
O1 C7 C8 C10 3.02(18) . . . . ?
N5 C7 C8 C10 -179.03(11) . . . . ?
O1 C7 C8 C11 123.57(13) . . . . ?
N5 C7 C8 C11 -58.48(14) . . . . ?
O1 C7 C8 C9 -116.02(14) . . . . ?
N5 C7 C8 C9 61.93(14) . . . . ?
C13 O3 C12 O4 67.87(12) . . . . ?
C13 O3 C12 C4 -174.62(10) . . . . ?
C14 O4 C12 O3 -139.15(11) . . . . ?
C14 O4 C12 C4 102.36(11) . . . . ?
N3 C4 C12 O3 163.68(10) . . . . ?
C3 C4 C12 O3 -19.63(16) . . . . ?
N3 C4 C12 O4 -77.17(12) . . . . ?
C3 C4 C12 O4 99.53(13) . . . . ?
C20 C15 C16 C17 0.83(18) . . . . ?
C20 C15 C16 N6 -178.47(11) . . . . ?
O7 N6 C16 C17 -167.42(12) . . . . ?
O8 N6 C16 C17 12.52(17) . . . . ?
O7 N6 C16 C15 11.91(17) . . . . ?
O8 N6 C16 C15 -168.15(11) . . . . ?
C15 C16 C17 C18 -0.55(19) . . . . ?
N6 C16 C17 C18 178.74(11) . . . . ?
C16 C17 C18 C19 -0.32(19) . . . . ?
C17 C18 C19 C20 0.9(2) . . . . ?
C16 C15 C20 C19 -0.23(18) . . . . ?
C16 C15 C20 C21 178.76(11) . . . . ?
C18 C19 C20 C15 -0.61(19) . . . . ?
C18 C19 C20 C21 -179.64(12) . . . . ?
C15 C20 C21 O6 -168.24(13) . . . . ?
C19 C20 C21 O6 10.77(19) . . . . ?
C15 C20 C21 O5 11.77(18) . . . . ?
C19 C20 C21 O5 -169.22(12) . . . . ?
_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full 29.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max 0.415
_refine_diff_density_min -0.284
_refine_diff_density_rms 0.052