# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012
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#
# Cambridge Crystallographic Data Centre
# CCDC
#
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#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
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# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
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data_I
_database_code_depnum_ccdc_archive 'CCDC 788427'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
4-Amino-2,8-dimethyl-6H-pyrimido[1,2-a][1,3,5]triazin-6-one
;
_chemical_name_common ?
_chemical_formula_moiety 'C8 H9 N5 O'
_chemical_formula_sum 'C8 H9 N5 O'
_chemical_formula_iupac 'C8 H9 N5 O'
_chemical_formula_weight 191.20
_chemical_melting_point 545
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P n a 21'
_symmetry_space_group_name_Hall 'P 2c -2n'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
_cell_length_a 11.1369(19)
_cell_length_b 18.913(3)
_cell_length_c 4.0311(7)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 849.1(3)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 614
_cell_measurement_theta_min 2.83
_cell_measurement_theta_max 26.80
_cell_measurement_temperature 100(2)
_cell_special_details ?
_exptl_crystal_description Needle
_exptl_crystal_colour Colourless
_exptl_crystal_size_max 0.60
_exptl_crystal_size_mid 0.08
_exptl_crystal_size_min 0.06
_exptl_crystal_density_diffrn 1.496
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 400
_exptl_absorpt_coefficient_mu 0.107
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2001)'
_exptl_absorpt_correction_T_min 0.9383
_exptl_absorpt_correction_T_max 0.9936
_exptl_special_details
;
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker SMART APEX CCD'
_diffrn_measurement_method '\f and \w'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 5774
_diffrn_reflns_av_R_equivalents 0.0503
_diffrn_reflns_av_sigmaI/netI 0.0376
_diffrn_reflns_theta_min 2.15
_diffrn_reflns_theta_max 27.49
_diffrn_reflns_theta_full 27.49
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -24
_diffrn_reflns_limit_k_max 22
_diffrn_reflns_limit_l_min -5
_diffrn_reflns_limit_l_max 4
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_reflns_number_total 1119
_reflns_number_gt 1019
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0588
_refine_ls_R_factor_gt 0.0527
_refine_ls_wR_factor_gt 0.1137
_refine_ls_wR_factor_ref 0.1169
_refine_ls_goodness_of_fit_ref 1.145
_refine_ls_restrained_S_all 1.144
_refine_ls_number_reflns 1119
_refine_ls_number_parameters 137
_refine_ls_number_restraints 1
_refine_ls_hydrogen_treatment mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+0.4545P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.334
_refine_diff_density_min -0.251
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_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^ >
\s(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.
;
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'
_computing_data_collection 'SMART (Bruker, 2001)'
_computing_cell_refinement 'SAINT (Bruker, 2001)'
_computing_data_reduction 'SAINT (Bruker, 2001)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL (Sheldrick, 2008)'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.61240(19) 0.88225(11) -0.2411(7) 0.0229(6) Uani d . 1 1 . .
N N1 0.3706(2) 0.71578(13) 0.3214(8) 0.0145(6) Uani d . 1 1 . .
N N2 0.5341(2) 0.67258(13) -0.0011(7) 0.0137(6) Uani d . 1 1 . .
N N3 0.4963(2) 0.79702(13) 0.0265(7) 0.0119(5) Uani d . 1 1 . .
N N4 0.3255(2) 0.83294(13) 0.3415(7) 0.0138(6) Uani d . 1 1 . .
N N5 0.6531(2) 0.74865(15) -0.2904(7) 0.0154(6) Uani d . 1 1 . .
H H51 0.673(3) 0.793(2) -0.326(11) 0.018(9) Uiso d . 1 1 . .
H H52 0.689(3) 0.7098(19) -0.349(11) 0.019(9) Uiso d . 1 1 . .
C C1 0.4393(3) 0.66472(15) 0.2008(8) 0.0134(6) Uani d . 1 1 . .
C C2 0.5625(2) 0.73778(15) -0.0888(8) 0.0128(6) Uani d . 1 1 . .
C C3 0.3965(2) 0.78262(15) 0.2314(8) 0.0121(6) Uani d . 1 1 . .
C C4 0.3465(2) 0.90073(15) 0.2475(9) 0.0139(6) Uani d . 1 1 . .
C C5 0.4418(3) 0.91978(16) 0.0552(8) 0.0147(6) Uani d . 1 1 . .
H H5 0.4531 0.9683 0.0019 0.018 Uiso calc R 1 1 . .
C C6 0.5246(3) 0.86906(15) -0.0674(8) 0.0155(7) Uani d . 1 1 . .
C C7 0.4091(3) 0.59100(15) 0.3046(10) 0.0191(7) Uani d . 1 1 . .
H H7A 0.4559 0.5784 0.5017 0.029 Uiso calc R 1 1 . .
H H7B 0.4282 0.5582 0.1239 0.029 Uiso calc R 1 1 . .
H H7C 0.3232 0.5880 0.3562 0.029 Uiso calc R 1 1 . .
C C8 0.2543(3) 0.95324(15) 0.3617(9) 0.0182(7) Uani d . 1 1 . .
H H8A 0.1796 0.9460 0.2381 0.027 Uiso calc R 1 1 . .
H H8B 0.2840 1.0013 0.3224 0.027 Uiso calc R 1 1 . .
H H8C 0.2392 0.9467 0.5992 0.027 Uiso calc R 1 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0225(11) 0.0152(11) 0.0310(14) -0.0048(8) 0.0116(12) 0.0017(11)
N1 0.0125(11) 0.0128(12) 0.0183(14) -0.0008(9) 0.0027(11) 0.0007(11)
N2 0.0132(11) 0.0131(13) 0.0149(13) -0.0011(9) -0.0009(11) -0.0029(11)
N3 0.0101(10) 0.0113(12) 0.0144(13) -0.0013(8) 0.0024(10) -0.0011(10)
N4 0.0116(10) 0.0137(12) 0.0162(13) -0.0004(9) 0.0017(11) -0.0011(11)
N5 0.0139(12) 0.0123(13) 0.0200(15) 0.0017(10) 0.0064(12) -0.0007(12)
C1 0.0124(12) 0.0152(14) 0.0126(15) -0.0014(11) -0.0034(12) -0.0002(13)
C2 0.0101(12) 0.0167(15) 0.0114(14) 0.0023(11) -0.0002(12) -0.0034(13)
C3 0.0108(12) 0.0161(14) 0.0096(14) -0.0022(10) 0.0013(12) -0.0003(13)
C4 0.0142(13) 0.0136(14) 0.0139(15) -0.0001(10) -0.0048(12) -0.0030(14)
C5 0.0190(14) 0.0085(14) 0.0165(16) -0.0027(11) -0.0031(13) -0.0007(12)
C6 0.0156(13) 0.0122(15) 0.0187(17) -0.0050(11) -0.0018(13) 0.0009(13)
C7 0.0215(14) 0.0126(14) 0.0232(18) -0.0004(11) 0.0046(15) 0.0005(13)
C8 0.0182(13) 0.0154(15) 0.0209(16) 0.0021(11) 0.0018(13) -0.0010(14)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 . 1.228(4) ?
N1 C1 . 1.324(4) ?
N1 C3 . 1.346(4) ?
N2 C2 . 1.321(4) ?
N2 C1 . 1.342(4) ?
N3 C3 . 1.411(4) ?
N3 C2 . 1.420(4) ?
N3 C6 . 1.449(4) ?
N4 C3 . 1.314(4) ?
N4 C4 . 1.357(4) ?
N5 C2 . 1.311(4) ?
N5 H51 . 0.89(4) ?
N5 H52 . 0.87(4) ?
C1 C7 . 1.494(4) ?
C4 C5 . 1.363(4) ?
C4 C8 . 1.501(4) ?
C5 C6 . 1.420(4) ?
C5 H5 . 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 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C3 . . 117.5(3) ?
C2 N2 C1 . . 117.0(2) ?
C3 N3 C2 . . 116.6(2) ?
C3 N3 C6 . . 120.4(2) ?
C2 N3 C6 . . 122.9(2) ?
C3 N4 C4 . . 119.1(3) ?
C2 N5 H51 . . 116(2) ?
C2 N5 H52 . . 113(2) ?
H51 N5 H52 . . 130(3) ?
N1 C1 N2 . . 126.6(3) ?
N1 C1 C7 . . 116.6(3) ?
N2 C1 C7 . . 116.8(3) ?
N5 C2 N2 . . 119.7(3) ?
N5 C2 N3 . . 118.6(3) ?
N2 C2 N3 . . 121.6(3) ?
N4 C3 N1 . . 117.4(3) ?
N4 C3 N3 . . 122.1(3) ?
N1 C3 N3 . . 120.5(3) ?
N4 C4 C5 . . 122.9(3) ?
N4 C4 C8 . . 114.9(3) ?
C5 C4 C8 . . 122.2(3) ?
C4 C5 C6 . . 121.7(3) ?
C4 C5 H5 . . 119.2 ?
C6 C5 H5 . . 119.2 ?
O1 C6 C5 . . 125.3(3) ?
O1 C6 N3 . . 120.9(3) ?
C5 C6 N3 . . 113.8(3) ?
C1 C7 H7A . . 109.5 ?
C1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C4 C8 H8A . . 109.5 ?
C4 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C4 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N1 C1 N2 . . . . 0.9(5) ?
C3 N1 C1 C7 . . . . 179.8(3) ?
C2 N2 C1 N1 . . . . 0.2(5) ?
C2 N2 C1 C7 . . . . -178.8(3) ?
C1 N2 C2 N5 . . . . -178.8(3) ?
C1 N2 C2 N3 . . . . 0.4(4) ?
C3 N3 C2 N5 . . . . 177.4(3) ?
C6 N3 C2 N5 . . . . -0.3(4) ?
C3 N3 C2 N2 . . . . -1.8(4) ?
C6 N3 C2 N2 . . . . -179.5(3) ?
C4 N4 C3 N1 . . . . -177.9(3) ?
C4 N4 C3 N3 . . . . 2.0(4) ?
C1 N1 C3 N4 . . . . 177.5(3) ?
C1 N1 C3 N3 . . . . -2.4(4) ?
C2 N3 C3 N4 . . . . -177.1(3) ?
C6 N3 C3 N4 . . . . 0.7(4) ?
C2 N3 C3 N1 . . . . 2.8(4) ?
C6 N3 C3 N1 . . . . -179.4(3) ?
C3 N4 C4 C5 . . . . -3.2(5) ?
C3 N4 C4 C8 . . . . 174.9(3) ?
N4 C4 C5 C6 . . . . 1.6(5) ?
C8 C4 C5 C6 . . . . -176.3(3) ?
C4 C5 C6 O1 . . . . -179.9(3) ?
C4 C5 C6 N3 . . . . 1.0(4) ?
C3 N3 C6 O1 . . . . 178.8(3) ?
C2 N3 C6 O1 . . . . -3.6(4) ?
C3 N3 C6 C5 . . . . -2.1(4) ?
C2 N3 C6 C5 . . . . 175.5(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N5 H51 O1 . 0.89(4) 1.84(4) 2.575(3) 139(3)
N5 H51 N1 3_564 0.89(4) 2.63(4) 2.961(4) 103(3)
N5 H52 N4 3_564 0.87(4) 2.12(4) 2.876(4) 144(3)
data_a224
_database_code_depnum_ccdc_archive 'CCDC 791289'
#TrackingRef '2274_web_deposit_cif_file_0_NikhilSachdeva_1283240104.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C10 H19 N5 O4'
_chemical_formula_weight 273.30
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 9.1448(13)
_cell_length_b 6.7638(10)
_cell_length_c 22.369(3)
_cell_angle_alpha 90.00
_cell_angle_beta 94.610(3)
_cell_angle_gamma 90.00
_cell_volume 1379.2(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 223(2)
_cell_measurement_reflns_used 2999
_cell_measurement_theta_min 2.77
_cell_measurement_theta_max 27.53
_exptl_crystal_description Block
_exptl_crystal_colour Colourless
_exptl_crystal_size_max 0.58
_exptl_crystal_size_mid 0.36
_exptl_crystal_size_min 0.16
_exptl_crystal_density_meas 'Not Measured'
_exptl_crystal_density_diffrn 1.316
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 584
_exptl_absorpt_coefficient_mu 0.103
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_min 0.9427
_exptl_absorpt_correction_T_max 0.9837
_exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 223(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 9324
_diffrn_reflns_av_R_equivalents 0.0250
_diffrn_reflns_av_sigmaI/netI 0.0288
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -29
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_theta_min 2.23
_diffrn_reflns_theta_max 27.50
_reflns_number_total 3155
_reflns_number_gt 2672
_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^)+(0.0883P)^2^+0.2263P] 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 3155
_refine_ls_number_parameters 200
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0611
_refine_ls_R_factor_gt 0.0530
_refine_ls_wR_factor_ref 0.1559
_refine_ls_wR_factor_gt 0.1473
_refine_ls_goodness_of_fit_ref 1.079
_refine_ls_restrained_S_all 1.079
_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 0.84718(12) 0.72183(19) 0.55465(6) 0.0524(3) Uani 1 1 d . . .
N1 N 0.42009(13) 0.71819(17) 0.59500(5) 0.0316(3) Uani 1 1 d . . .
N2 N 0.59926(12) 0.73760(15) 0.52282(5) 0.0276(3) Uani 1 1 d . . .
N3 N 0.34049(12) 0.76029(16) 0.49728(5) 0.0287(3) Uani 1 1 d . . .
N4 N 0.51142(13) 0.77727(17) 0.42156(5) 0.0329(3) Uani 1 1 d . . .
N5 N 0.26226(13) 0.79822(18) 0.39806(5) 0.0347(3) Uani 1 1 d . . .
C1 C 0.45291(14) 0.73888(17) 0.53910(6) 0.0256(3) Uani 1 1 d . . .
C2 C 0.53152(17) 0.6943(2) 0.63856(6) 0.0364(3) Uani 1 1 d . . .
C3 C 0.67544(17) 0.6919(2) 0.62711(7) 0.0387(4) Uani 1 1 d . . .
H3 H 0.7471 0.6733 0.6592 0.046 Uiso 1 1 calc R . .
C4 C 0.72071(15) 0.7165(2) 0.56871(7) 0.0354(3) Uani 1 1 d . . .
C5 C 0.62035(15) 0.75725(19) 0.46141(7) 0.0316(3) Uani 1 1 d . . .
C6 C 0.37186(14) 0.77820(18) 0.44054(6) 0.0272(3) Uani 1 1 d . . .
C7 C 0.4833(2) 0.6710(3) 0.70062(7) 0.0551(5) Uani 1 1 d . . .
H7A H 0.5688 0.6597 0.7290 0.083 Uiso 1 1 calc R . .
H7B H 0.4238 0.5528 0.7024 0.083 Uiso 1 1 calc R . .
H7C H 0.4262 0.7855 0.7106 0.083 Uiso 1 1 calc R . .
C8 C 0.76954(18) 0.7550(3) 0.43883(8) 0.0531(5) Uani 1 1 d . . .
H8A H 0.7607 0.7636 0.3954 0.080 Uiso 1 1 calc R . .
H8B H 0.8192 0.6331 0.4511 0.080 Uiso 1 1 calc R . .
H8C H 0.8257 0.8668 0.4553 0.080 Uiso 1 1 calc R . .
C9 C 0.28582(19) 0.8151(3) 0.33434(6) 0.0450(4) Uani 1 1 d . . .
H9A H 0.3892 0.8369 0.3299 0.067 Uiso 1 1 calc R . .
H9B H 0.2294 0.9254 0.3170 0.067 Uiso 1 1 calc R . .
H9C H 0.2545 0.6940 0.3139 0.067 Uiso 1 1 calc R . .
C10 C 0.11000(17) 0.7911(3) 0.41339(8) 0.0437(4) Uani 1 1 d . . .
H10A H 0.1076 0.7885 0.4566 0.066 Uiso 1 1 calc R . .
H10B H 0.0632 0.6730 0.3963 0.066 Uiso 1 1 calc R . .
H10C H 0.0581 0.9070 0.3974 0.066 Uiso 1 1 calc R . .
O1W O 0.10448(18) 0.0784(2) 0.21101(6) 0.0588(4) Uani 1 1 d . . .
H1W H 0.026(3) 0.054(4) 0.2268(12) 0.097(9) Uiso 1 1 d . . .
H2W H 0.115(2) -0.021(4) 0.1856(10) 0.069(6) Uiso 1 1 d . . .
O2W O 0.13730(16) 0.4805(2) 0.22458(6) 0.0572(4) Uani 1 1 d . . .
H3W H 0.128(3) 0.368(5) 0.2125(11) 0.090(9) Uiso 1 1 d . . .
H4W H 0.132(2) 0.552(3) 0.1914(10) 0.060(6) Uiso 1 1 d . . .
O3W O 0.12489(14) 0.75885(18) 0.12827(5) 0.0437(3) Uani 1 1 d . . .
H5W H 0.206(3) 0.767(3) 0.1128(11) 0.065(6) Uiso 1 1 d . . .
H6W H 0.052(3) 0.760(3) 0.1034(12) 0.067(7) 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 0.0252(6) 0.0721(9) 0.0587(7) 0.0005(6) -0.0045(5) 0.0000(5)
N1 0.0329(6) 0.0355(6) 0.0265(6) 0.0007(4) 0.0021(4) 0.0008(5)
N2 0.0243(6) 0.0257(6) 0.0324(6) -0.0020(4) 0.0007(4) -0.0006(4)
N3 0.0253(5) 0.0333(6) 0.0274(6) -0.0015(4) 0.0020(4) 0.0012(4)
N4 0.0323(6) 0.0371(6) 0.0301(6) -0.0031(5) 0.0064(5) -0.0032(5)
N5 0.0342(6) 0.0406(7) 0.0285(6) -0.0013(5) -0.0020(5) 0.0021(5)
C1 0.0252(6) 0.0220(6) 0.0296(6) -0.0028(5) 0.0027(5) 0.0006(4)
C2 0.0435(8) 0.0340(7) 0.0307(7) 0.0004(5) -0.0035(6) 0.0004(6)
C3 0.0391(8) 0.0384(8) 0.0365(8) 0.0020(6) -0.0108(6) 0.0007(6)
C4 0.0269(7) 0.0320(7) 0.0457(8) -0.0024(6) -0.0057(6) 0.0003(5)
C5 0.0282(7) 0.0308(7) 0.0366(7) -0.0048(5) 0.0081(5) -0.0027(5)
C6 0.0299(7) 0.0234(6) 0.0286(6) -0.0035(5) 0.0034(5) -0.0002(5)
C7 0.0602(11) 0.0764(13) 0.0281(8) 0.0058(8) -0.0009(7) 0.0046(9)
C8 0.0320(8) 0.0834(14) 0.0458(9) -0.0071(8) 0.0143(7) -0.0045(8)
C9 0.0558(10) 0.0516(10) 0.0265(7) 0.0009(6) -0.0039(6) -0.0021(7)
C10 0.0314(7) 0.0547(10) 0.0436(8) -0.0020(7) -0.0071(6) 0.0045(6)
O1W 0.0780(10) 0.0484(8) 0.0513(7) 0.0001(6) 0.0124(7) 0.0032(7)
O2W 0.0818(10) 0.0545(8) 0.0356(6) -0.0031(6) 0.0055(6) -0.0132(7)
O3W 0.0355(6) 0.0605(8) 0.0355(6) 0.0011(5) 0.0048(5) -0.0028(5)
_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 C4 1.2232(19) . ?
N1 C1 1.3167(17) . ?
N1 C2 1.3617(18) . ?
N2 C5 1.4088(18) . ?
N2 C1 1.4150(17) . ?
N2 C4 1.4575(17) . ?
N3 C6 1.3291(17) . ?
N3 C1 1.3411(17) . ?
N4 C5 1.2894(19) . ?
N4 C6 1.3770(17) . ?
N5 C6 1.3315(17) . ?
N5 C10 1.4613(19) . ?
N5 C9 1.4631(18) . ?
C2 C3 1.361(2) . ?
C2 C7 1.498(2) . ?
C3 C4 1.412(2) . ?
C3 H3 0.9400 . ?
C5 C8 1.4924(19) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
O1W H1W 0.84(3) . ?
O1W H2W 0.89(3) . ?
O2W H3W 0.81(3) . ?
O2W H4W 0.88(2) . ?
O3W H5W 0.85(3) . ?
O3W H6W 0.83(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
C1 N1 C2 118.52(12) . . ?
C5 N2 C1 117.18(11) . . ?
C5 N2 C4 122.67(12) . . ?
C1 N2 C4 120.15(11) . . ?
C6 N3 C1 117.63(12) . . ?
C5 N4 C6 118.10(12) . . ?
C6 N5 C10 120.40(12) . . ?
C6 N5 C9 122.81(13) . . ?
C10 N5 C9 116.67(12) . . ?
N1 C1 N3 116.96(12) . . ?
N1 C1 N2 122.43(12) . . ?
N3 C1 N2 120.60(12) . . ?
C3 C2 N1 123.10(13) . . ?
C3 C2 C7 122.29(14) . . ?
N1 C2 C7 114.61(14) . . ?
C2 C3 C4 122.20(13) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
O1 C4 C3 126.52(14) . . ?
O1 C4 N2 119.92(14) . . ?
C3 C4 N2 113.56(12) . . ?
N4 C5 N2 121.69(12) . . ?
N4 C5 C8 116.33(13) . . ?
N2 C5 C8 121.98(13) . . ?
N3 C6 N5 118.88(12) . . ?
N3 C6 N4 124.79(12) . . ?
N5 C6 N4 116.34(12) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N5 C9 H9A 109.5 . . ?
N5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N5 C10 H10A 109.5 . . ?
N5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H1W O1W H2W 105(2) . . ?
H3W O2W H4W 104(2) . . ?
H5W O3W H6W 114(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 N3 179.40(12) . . . . ?
C2 N1 C1 N2 -0.16(18) . . . . ?
C6 N3 C1 N1 -178.96(11) . . . . ?
C6 N3 C1 N2 0.60(17) . . . . ?
C5 N2 C1 N1 178.81(11) . . . . ?
C4 N2 C1 N1 -1.17(18) . . . . ?
C5 N2 C1 N3 -0.73(17) . . . . ?
C4 N2 C1 N3 179.28(11) . . . . ?
C1 N1 C2 C3 0.4(2) . . . . ?
C1 N1 C2 C7 -179.73(13) . . . . ?
N1 C2 C3 C4 0.7(2) . . . . ?
C7 C2 C3 C4 -179.12(15) . . . . ?
C2 C3 C4 O1 177.86(15) . . . . ?
C2 C3 C4 N2 -1.9(2) . . . . ?
C5 N2 C4 O1 2.3(2) . . . . ?
C1 N2 C4 O1 -177.68(12) . . . . ?
C5 N2 C4 C3 -177.88(12) . . . . ?
C1 N2 C4 C3 2.10(17) . . . . ?
C6 N4 C5 N2 -0.28(19) . . . . ?
C6 N4 C5 C8 179.40(12) . . . . ?
C1 N2 C5 N4 0.57(18) . . . . ?
C4 N2 C5 N4 -179.45(12) . . . . ?
C1 N2 C5 C8 -179.10(12) . . . . ?
C4 N2 C5 C8 0.89(19) . . . . ?
C1 N3 C6 N5 179.52(12) . . . . ?
C1 N3 C6 N4 -0.31(18) . . . . ?
C10 N5 C6 N3 -2.89(19) . . . . ?
C9 N5 C6 N3 -178.79(12) . . . . ?
C10 N5 C6 N4 176.95(12) . . . . ?
C9 N5 C6 N4 1.05(19) . . . . ?
C5 N4 C6 N3 0.14(19) . . . . ?
C5 N4 C6 N5 -179.69(12) . . . . ?
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
O1W H1W O2W 0.84(3) 1.98(3) 2.813(2) 170(3) 2_545
O1W H2W O3W 0.89(3) 1.97(3) 2.8614(19) 177(2) 1_545
O2W H3W O1W 0.81(3) 1.97(3) 2.751(2) 161(3) .
O2W H4W O3W 0.88(2) 1.98(2) 2.8565(19) 168.5(19) .
O3W H5W N1 0.85(3) 2.03(3) 2.8615(17) 167(2) 4_575
O3W H6W O1 0.83(3) 2.09(3) 2.9165(17) 169(2) 4_475
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.309
_refine_diff_density_min -0.251
_refine_diff_density_rms 0.071
data_b367
_database_code_depnum_ccdc_archive 'CCDC 838638'
#TrackingRef '6667_web_deposit_cif_file_0_NikhilSachdeva_1312957270.B367.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C14 H20 N6 O'
_chemical_formula_weight 288.36
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 Orthorhombic
_symmetry_space_group_name_H-M Pna2(1)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
_cell_length_a 7.4179(9)
_cell_length_b 11.2238(15)
_cell_length_c 17.288(2)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1439.4(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 707
_cell_measurement_theta_min 2.16
_cell_measurement_theta_max 23.52
_exptl_crystal_description Block
_exptl_crystal_colour Yellow
_exptl_crystal_size_max 0.34
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.12
_exptl_crystal_density_meas 'Not measured'
_exptl_crystal_density_diffrn 1.331
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 616
_exptl_absorpt_coefficient_mu 0.090
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_min 0.9701
_exptl_absorpt_correction_T_max 0.9893
_exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)'
_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 9771
_diffrn_reflns_av_R_equivalents 0.0389
_diffrn_reflns_av_sigmaI/netI 0.0393
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_theta_min 2.16
_diffrn_reflns_theta_max 27.48
_reflns_number_total 2799
_reflns_number_gt 2597
_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^)+(0.0735P)^2^+0.1541P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.5(16)
_refine_ls_number_reflns 2799
_refine_ls_number_parameters 196
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0519
_refine_ls_R_factor_gt 0.0478
_refine_ls_wR_factor_ref 0.1193
_refine_ls_wR_factor_gt 0.1168
_refine_ls_goodness_of_fit_ref 1.061
_refine_ls_restrained_S_all 1.061
_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 0.1431(2) 0.41278(14) 0.60503(9) 0.0270(4) Uani 1 1 d . . .
N1 N 0.2399(2) 0.46062(15) 0.48064(11) 0.0132(4) Uani 1 1 d . . .
N2 N 0.2426(2) 0.30958(16) 0.38296(11) 0.0159(4) Uani 1 1 d . . .
N3 N 0.2827(2) 0.66005(16) 0.43943(11) 0.0170(4) Uani 1 1 d . . .
N4 N 0.2453(2) 0.50488(18) 0.34560(11) 0.0162(4) Uani 1 1 d . . .
N5 N 0.2254(3) 0.70268(17) 0.31206(11) 0.0196(4) Uani 1 1 d . . .
N6 N 0.4657(2) 0.73146(15) 0.67068(11) 0.0176(4) Uani 1 1 d . . .
C1 C 0.1868(3) 0.37752(19) 0.54063(13) 0.0194(4) Uani 1 1 d . . .
C2 C 0.2431(2) 0.42352(19) 0.40248(12) 0.0149(4) Uani 1 1 d . . .
C3 C 0.2244(3) 0.22778(19) 0.44074(13) 0.0166(4) Uani 1 1 d . . .
C4 C 0.1911(3) 0.25645(19) 0.51574(13) 0.0197(5) Uani 1 1 d . . .
H4 H 0.1702 0.1947 0.5523 0.024 Uiso 1 1 calc R . .
C5 C 0.2371(3) 0.0997(2) 0.41533(14) 0.0219(5) Uani 1 1 d . . .
H5A H 0.1397 0.0822 0.3788 0.033 Uiso 1 1 calc R . .
H5B H 0.2262 0.0475 0.4605 0.033 Uiso 1 1 calc R . .
H5C H 0.3537 0.0861 0.3902 0.033 Uiso 1 1 calc R . .
C6 C 0.2900(2) 0.58208(17) 0.49609(13) 0.0145(4) Uani 1 1 d . . .
C7 C 0.2483(3) 0.6195(2) 0.36712(14) 0.0163(4) Uani 1 1 d . . .
C8 C 0.2281(4) 0.8298(2) 0.33139(14) 0.0245(5) Uani 1 1 d . . .
H8A H 0.1233 0.8490 0.3636 0.037 Uiso 1 1 calc R . .
H8B H 0.2237 0.8769 0.2837 0.037 Uiso 1 1 calc R . .
H8C H 0.3389 0.8484 0.3598 0.037 Uiso 1 1 calc R . .
C9 C 0.1942(4) 0.6706(2) 0.23165(14) 0.0264(5) Uani 1 1 d . . .
H9A H 0.2823 0.6104 0.2157 0.040 Uiso 1 1 calc R . .
H9B H 0.2070 0.7415 0.1990 0.040 Uiso 1 1 calc R . .
H9C H 0.0721 0.6383 0.2260 0.040 Uiso 1 1 calc R . .
C10 C 0.3548(3) 0.60826(19) 0.57085(13) 0.0166(4) Uani 1 1 d . . .
H10 H 0.3745 0.5428 0.6046 0.020 Uiso 1 1 calc R . .
C11 C 0.3928(3) 0.72208(18) 0.59982(13) 0.0163(4) Uani 1 1 d . . .
C12 C 0.3514(3) 0.83457(19) 0.55614(13) 0.0189(4) Uani 1 1 d . . .
H12A H 0.3481 0.9019 0.5922 0.028 Uiso 1 1 calc R . .
H12B H 0.2341 0.8268 0.5306 0.028 Uiso 1 1 calc R . .
H12C H 0.4450 0.8483 0.5172 0.028 Uiso 1 1 calc R . .
C13 C 0.5057(3) 0.62578(19) 0.71609(13) 0.0233(5) Uani 1 1 d . . .
H13A H 0.3934 0.5835 0.7278 0.035 Uiso 1 1 calc R . .
H13B H 0.5647 0.6492 0.7645 0.035 Uiso 1 1 calc R . .
H13C H 0.5860 0.5733 0.6866 0.035 Uiso 1 1 calc R . .
C14 C 0.5075(3) 0.84548(19) 0.70928(13) 0.0210(5) Uani 1 1 d . . .
H14A H 0.5354 0.9060 0.6702 0.031 Uiso 1 1 calc R . .
H14B H 0.6116 0.8349 0.7435 0.031 Uiso 1 1 calc R . .
H14C H 0.4032 0.8712 0.7398 0.031 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 0.0409(10) 0.0229(8) 0.0171(8) -0.0013(7) 0.0106(7) -0.0058(7)
N1 0.0156(8) 0.0121(8) 0.0118(9) -0.0004(7) 0.0011(6) -0.0004(6)
N2 0.0196(8) 0.0142(9) 0.0140(9) -0.0020(7) -0.0001(7) 0.0004(6)
N3 0.0211(8) 0.0145(8) 0.0155(10) -0.0017(7) 0.0004(7) -0.0004(6)
N4 0.0220(9) 0.0145(8) 0.0122(9) -0.0021(7) -0.0007(7) 0.0017(7)
N5 0.0305(10) 0.0154(9) 0.0129(10) -0.0005(8) -0.0031(7) -0.0007(7)
N6 0.0202(9) 0.0184(9) 0.0141(9) -0.0016(8) -0.0012(7) 0.0002(7)
C1 0.0222(10) 0.0196(11) 0.0165(11) 0.0012(9) 0.0002(8) 0.0000(8)
C2 0.0140(9) 0.0176(10) 0.0133(11) -0.0024(9) 0.0006(8) 0.0014(7)
C3 0.0167(9) 0.0147(10) 0.0183(11) -0.0005(9) -0.0018(8) -0.0013(7)
C4 0.0257(11) 0.0161(10) 0.0174(12) 0.0028(8) 0.0003(9) -0.0026(8)
C5 0.0352(13) 0.0120(10) 0.0185(12) -0.0010(9) 0.0004(9) 0.0009(8)
C6 0.0130(9) 0.0145(10) 0.0160(10) -0.0017(8) 0.0022(8) 0.0005(7)
C7 0.0177(10) 0.0166(11) 0.0146(11) -0.0020(9) 0.0004(8) -0.0003(7)
C8 0.0413(14) 0.0129(11) 0.0194(13) 0.0022(9) -0.0035(9) 0.0014(9)
C9 0.0460(14) 0.0196(11) 0.0137(11) -0.0006(9) -0.0057(10) -0.0008(10)
C10 0.0189(10) 0.0170(10) 0.0139(10) 0.0028(8) -0.0005(8) 0.0003(8)
C11 0.0160(10) 0.0183(10) 0.0146(10) -0.0010(8) 0.0022(8) 0.0000(7)
C12 0.0247(11) 0.0161(10) 0.0160(11) -0.0006(8) -0.0007(8) -0.0005(8)
C13 0.0305(12) 0.0226(11) 0.0167(11) -0.0002(10) -0.0080(9) 0.0003(8)
C14 0.0234(10) 0.0247(12) 0.0148(10) -0.0044(9) 0.0007(9) -0.0046(9)
_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 1.225(3) . ?
N1 C2 1.414(3) . ?
N1 C6 1.438(2) . ?
N1 C1 1.449(3) . ?
N2 C2 1.323(3) . ?
N2 C3 1.363(3) . ?
N3 C6 1.315(3) . ?
N3 C7 1.354(3) . ?
N4 C7 1.340(3) . ?
N4 C2 1.342(3) . ?
N5 C7 1.344(3) . ?
N5 C9 1.455(3) . ?
N5 C8 1.465(3) . ?
N6 C11 1.343(3) . ?
N6 C13 1.453(3) . ?
N6 C14 1.476(3) . ?
C1 C4 1.426(3) . ?
C3 C4 1.359(3) . ?
C3 C5 1.506(3) . ?
C6 C10 1.410(3) . ?
C10 C11 1.401(3) . ?
C11 C12 1.503(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
C2 N1 C6 116.89(18) . . ?
C2 N1 C1 119.93(17) . . ?
C6 N1 C1 123.18(19) . . ?
C2 N2 C3 117.68(19) . . ?
C6 N3 C7 118.16(18) . . ?
C7 N4 C2 116.75(19) . . ?
C7 N5 C9 121.68(19) . . ?
C7 N5 C8 120.85(19) . . ?
C9 N5 C8 117.46(19) . . ?
C11 N6 C13 120.73(18) . . ?
C11 N6 C14 124.38(18) . . ?
C13 N6 C14 114.87(18) . . ?
O1 C1 C4 126.0(2) . . ?
O1 C1 N1 120.95(19) . . ?
C4 C1 N1 113.04(19) . . ?
N2 C2 N4 118.10(19) . . ?
N2 C2 N1 121.9(2) . . ?
N4 C2 N1 120.00(18) . . ?
C4 C3 N2 123.90(19) . . ?
C4 C3 C5 121.0(2) . . ?
N2 C3 C5 115.02(19) . . ?
C3 C4 C1 121.2(2) . . ?
N3 C6 C10 123.94(18) . . ?
N3 C6 N1 118.81(19) . . ?
C10 C6 N1 117.13(18) . . ?
N4 C7 N5 117.9(2) . . ?
N4 C7 N3 125.6(2) . . ?
N5 C7 N3 116.38(19) . . ?
C11 C10 C6 125.91(19) . . ?
N6 C11 C10 118.59(19) . . ?
N6 C11 C12 118.34(18) . . ?
C10 C11 C12 123.05(19) . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 27.48
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.361
_refine_diff_density_min -0.223
_refine_diff_density_rms 0.059