# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 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 
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data_Compound1
_database_code_depnum_ccdc_archive 'CCDC 676429'
_audit_creation_method           SHELXTL
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 N5 O2'
_chemical_formula_weight         319.32
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   P2(1)2(1)2(1)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
_cell_length_a                   17.1841(9)
_cell_length_b                   12.4648(7)
_cell_length_c                   6.7661(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1449.27(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3640
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      28.17
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      173(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            8480
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         28.29
_reflns_number_total             3229
_reflns_number_gt                2850
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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^)+(0.0507P)^2^+1.0133P] 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(3)
_refine_ls_number_reflns         3229
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0718
_refine_ls_wR_factor_ref         0.1478
_refine_ls_wR_factor_gt          0.1438
_refine_ls_goodness_of_fit_ref   1.215
_refine_ls_restrained_S_all      1.215
_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 0.15274(12) -0.29808(18) 0.7785(4) 0.0346(6) Uani 1 1 d . . .
O2 O 0.43724(12) 0.20313(17) 0.7550(4) 0.0308(6) Uani 1 1 d . . .
N1 N -0.13425(15) -0.2420(2) 0.7230(4) 0.0290(7) Uani 1 1 d . . .
N2 N 0.14580(14) -0.1159(2) 0.7828(4) 0.0241(6) Uani 1 1 d . . .
H2N H 0.1121 -0.0628 0.7809 0.029 Uiso 1 1 calc R . .
N3 N 0.23375(13) 0.0208(2) 0.7882(4) 0.0207(5) Uani 1 1 d . . .
N4 N 0.30699(14) 0.17326(19) 0.7887(4) 0.0221(6) Uani 1 1 d . . .
H4N H 0.2617 0.2060 0.7972 0.027 Uiso 1 1 calc R . .
N5 N 0.33362(15) 0.5784(2) 0.7453(5) 0.0284(6) Uani 1 1 d . . .
C1 C -0.00545(18) -0.3099(3) 0.6710(5) 0.0277(8) Uani 1 1 d . . .
H1 H 0.0268 -0.3657 0.6217 0.033 Uiso 1 1 calc R . .
C2 C -0.08551(19) -0.3170(3) 0.6555(5) 0.0284(8) Uani 1 1 d . . .
H2 H -0.1070 -0.3786 0.5934 0.034 Uiso 1 1 calc R . .
C3 C -0.10239(19) -0.1568(3) 0.8084(5) 0.0311(8) Uani 1 1 d . . .
H3 H -0.1361 -0.1025 0.8569 0.037 Uiso 1 1 calc R . .
C4 C -0.02230(19) -0.1421(3) 0.8314(5) 0.0281(8) Uani 1 1 d . . .
H4 H -0.0023 -0.0799 0.8948 0.034 Uiso 1 1 calc R . .
C5 C 0.02704(16) -0.2203(2) 0.7593(5) 0.0210(6) Uani 1 1 d . . .
C6 C 0.11473(17) -0.2163(2) 0.7751(5) 0.0217(6) Uani 1 1 d . . .
C7 C 0.22488(16) -0.0854(2) 0.7932(5) 0.0206(6) Uani 1 1 d . . .
C8 C 0.28645(17) -0.1578(2) 0.8069(5) 0.0234(7) Uani 1 1 d . . .
H8 H 0.2782 -0.2332 0.8093 0.028 Uiso 1 1 calc R . .
C9 C 0.35970(18) -0.1141(2) 0.8167(5) 0.0258(7) Uani 1 1 d . . .
H9 H 0.4033 -0.1605 0.8285 0.031 Uiso 1 1 calc R . .
C10 C 0.37202(17) -0.0046(2) 0.8099(5) 0.0259(7) Uani 1 1 d . . .
H10 H 0.4229 0.0251 0.8144 0.031 Uiso 1 1 calc R . .
C11 C 0.30606(17) 0.0602(2) 0.7960(4) 0.0192(6) Uani 1 1 d . . .
C12 C 0.37103(17) 0.2369(2) 0.7697(4) 0.0194(6) Uani 1 1 d . . .
C13 C 0.35512(16) 0.3561(2) 0.7647(4) 0.0198(6) Uani 1 1 d . . .
C14 C 0.29059(18) 0.4038(2) 0.8497(5) 0.0218(7) Uani 1 1 d . . .
H14 H 0.2530 0.3620 0.9181 0.026 Uiso 1 1 calc R . .
C15 C 0.28189(18) 0.5141(3) 0.8328(5) 0.0278(7) Uani 1 1 d . . .
H15 H 0.2364 0.5458 0.8869 0.033 Uiso 1 1 calc R . .
C16 C 0.39721(19) 0.5316(3) 0.6711(5) 0.0280(7) Uani 1 1 d . . .
H16 H 0.4356 0.5761 0.6117 0.034 Uiso 1 1 calc R . .
C17 C 0.41034(18) 0.4220(3) 0.6758(5) 0.0256(7) Uani 1 1 d . . .
H17 H 0.4562 0.3924 0.6195 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 0.0228(11) 0.0221(11) 0.0590(17) 0.0011(13) 0.0016(12) 0.0041(9)
O2 0.0210(11) 0.0218(11) 0.0496(15) -0.0021(12) 0.0023(11) 0.0009(9)
N1 0.0233(13) 0.0317(15) 0.0320(16) 0.0014(13) 0.0008(14) -0.0024(11)
N2 0.0189(12) 0.0171(12) 0.0363(15) 0.0013(12) 0.0027(12) 0.0020(10)
N3 0.0187(12) 0.0191(12) 0.0243(14) -0.0019(11) 0.0025(10) 0.0034(10)
N4 0.0193(12) 0.0160(12) 0.0309(15) -0.0035(12) -0.0007(11) 0.0063(9)
N5 0.0307(14) 0.0178(13) 0.0366(16) 0.0024(13) -0.0062(13) -0.0020(11)
C1 0.0252(16) 0.0197(17) 0.038(2) 0.0002(15) 0.0044(14) -0.0017(13)
C2 0.0285(17) 0.0248(18) 0.0321(18) 0.0008(14) 0.0014(14) -0.0103(14)
C3 0.0247(16) 0.0343(18) 0.0343(19) -0.0051(16) 0.0021(15) 0.0048(14)
C4 0.0271(17) 0.0251(18) 0.0322(18) -0.0090(15) -0.0017(14) -0.0025(14)
C5 0.0230(14) 0.0210(15) 0.0190(15) 0.0044(13) 0.0025(13) -0.0009(12)
C6 0.0228(14) 0.0214(15) 0.0210(16) 0.0028(13) 0.0018(13) -0.0009(12)
C7 0.0241(15) 0.0191(14) 0.0187(16) -0.0014(13) 0.0005(12) 0.0011(11)
C8 0.0252(16) 0.0182(14) 0.0268(18) 0.0014(14) 0.0014(13) 0.0032(12)
C9 0.0208(14) 0.0244(16) 0.0323(17) -0.0001(14) -0.0027(14) 0.0113(13)
C10 0.0198(15) 0.0263(17) 0.0314(17) 0.0009(14) -0.0004(14) -0.0008(13)
C11 0.0218(14) 0.0196(14) 0.0161(14) 0.0012(12) 0.0002(12) 0.0007(12)
C12 0.0205(15) 0.0179(14) 0.0197(15) -0.0027(12) -0.0012(13) 0.0017(11)
C13 0.0185(14) 0.0200(15) 0.0210(15) 0.0020(12) -0.0085(12) -0.0011(11)
C14 0.0189(15) 0.0210(15) 0.0255(17) -0.0039(13) -0.0001(12) -0.0035(12)
C15 0.0240(16) 0.0257(16) 0.0339(19) -0.0065(15) -0.0063(14) 0.0060(14)
C16 0.0242(16) 0.0233(16) 0.0364(18) 0.0034(15) -0.0034(14) -0.0054(13)
C17 0.0201(15) 0.0251(17) 0.0316(18) -0.0020(14) -0.0002(13) -0.0012(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 C6 1.211(4) . ?
O2 C12 1.217(3) . ?
N1 C3 1.327(4) . ?
N1 C2 1.336(4) . ?
N2 C6 1.362(4) . ?
N2 C7 1.413(4) . ?
N3 C7 1.333(4) . ?
N3 C11 1.337(4) . ?
N4 C12 1.363(4) . ?
N4 C11 1.411(4) . ?
N5 C15 1.336(4) . ?
N5 C16 1.336(4) . ?
C1 C2 1.383(5) . ?
C1 C5 1.385(4) . ?
C3 C4 1.397(5) . ?
C4 C5 1.381(4) . ?
C5 C6 1.511(4) . ?
C7 C8 1.394(4) . ?
C8 C9 1.373(4) . ?
C9 C10 1.382(4) . ?
C10 C11 1.395(4) . ?
C12 C13 1.511(4) . ?
C13 C14 1.384(4) . ?
C13 C17 1.392(4) . ?
C14 C15 1.387(5) . ?
C16 C17 1.385(4) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C2 116.8(3) . . ?
C6 N2 C7 128.8(2) . . ?
C7 N3 C11 118.0(2) . . ?
C12 N4 C11 126.5(2) . . ?
C15 N5 C16 116.7(3) . . ?
C2 C1 C5 119.1(3) . . ?
N1 C2 C1 123.6(3) . . ?
N1 C3 C4 124.1(3) . . ?
C5 C4 C3 118.2(3) . . ?
C4 C5 C1 118.3(3) . . ?
C4 C5 C6 124.3(3) . . ?
C1 C5 C6 117.3(3) . . ?
O1 C6 N2 124.2(3) . . ?
O1 C6 C5 120.7(3) . . ?
N2 C6 C5 115.1(3) . . ?
N3 C7 C8 123.9(3) . . ?
N3 C7 N2 112.1(2) . . ?
C8 C7 N2 124.0(3) . . ?
C9 C8 C7 116.2(3) . . ?
C8 C9 C10 122.1(3) . . ?
C9 C10 C11 116.7(3) . . ?
N3 C11 C10 123.1(3) . . ?
N3 C11 N4 112.1(2) . . ?
C10 C11 N4 124.9(3) . . ?
O2 C12 N4 124.1(3) . . ?
O2 C12 C13 120.5(3) . . ?
N4 C12 C13 115.4(2) . . ?
C14 C13 C17 118.2(3) . . ?
C14 C13 C12 123.9(3) . . ?
C17 C13 C12 117.8(3) . . ?
C13 C14 C15 118.6(3) . . ?
N5 C15 C14 124.0(3) . . ?
N5 C16 C17 123.7(3) . . ?
C16 C17 C13 118.8(3) . . ?
_diffrn_measured_fraction_theta_max 0.937
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.937
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.085


data_aaa
_database_code_depnum_ccdc_archive 'CCDC 905197'
_audit_creation_method SHELXTL
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum
'C34 H26 N10 O4'
_chemical_formula_weight 638.65
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 8.3304(6)
_cell_length_b 16.7637(12)
_cell_length_c 20.9646(15)
_cell_angle_alpha 90.00
_cell_angle_beta 92.043(4)
_cell_angle_gamma 90.00
_cell_volume 2925.8(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 7163
_cell_measurement_theta_min 2.29
_cell_measurement_theta_max 22.89
_exptl_crystal_description plate
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.12
_exptl_crystal_size_mid 0.08
_exptl_crystal_size_min 0.03
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.450
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1328
_exptl_absorpt_coefficient_mu 0.100
_exptl_absorpt_correction_type 'multi-scan'
_exptl_absorpt_correction_T_min 0.9881
_exptl_absorpt_correction_T_max 0.9970
_exptl_absorpt_process_details SADABS
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(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 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 43040
_diffrn_reflns_av_R_equivalents 0.0611
_diffrn_reflns_av_sigmaI/netI 0.0558
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -22
_diffrn_reflns_limit_k_max 22
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_limit_l_max 27
_diffrn_reflns_theta_min 1.56
_diffrn_reflns_theta_max 28.40
_reflns_number_total 7310
_reflns_number_gt 4398
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker APEX2'
_computing_cell_refinement 'Bruker SAINT'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 7310
_refine_ls_number_parameters 434
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1072
_refine_ls_R_factor_gt 0.0588
_refine_ls_wR_factor_ref 0.1906
_refine_ls_wR_factor_gt 0.1640
_refine_ls_goodness_of_fit_ref 1.111
_refine_ls_restrained_S_all 1.111
_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 0.3876(2) 0.82535(10) 0.34252(7) 0.0479(4) Uani 1 1 d . . .
O2 O 0.91318(19) 1.13423(9) 0.53744(7) 0.0427(4) Uani 1 1 d . . .
O3 O 0.4300(2) 0.10379(10) 0.27574(8) 0.0600(5) Uani 1 1 d . . .
O4 O 0.0059(2) 0.11044(10) -0.06693(8) 0.0559(5) Uani 1 1 d . . .
N2 N 0.5113(2) 0.82648(10) 0.44120(8) 0.0315(4) Uani 1 1 d . . .
H2A H 0.5259 0.7991 0.4756 0.038 Uiso 1 1 calc R . .
N3 N 0.66491(19) 0.92163(10) 0.49388(8) 0.0287(4) Uani 1 1 d . . .
N4 N 0.8144(2) 1.00994(10) 0.55521(8) 0.0304(4) Uani 1 1 d . . .
H4A H 0.8142 0.9724 0.5831 0.037 Uiso 1 1 calc R . .
N7 N 0.3052(2) 0.19541(10) 0.21104(8) 0.0329(4) Uani 1 1 d . . .
H7A H 0.2772 0.2448 0.2092 0.040 Uiso 1 1 calc R . .
N8 N 0.1864(2) 0.18975(10) 0.11136(8) 0.0294(4) Uani 1 1 d . . .
N9 N 0.0636(2) 0.19930(10) 0.01250(8) 0.0350(4) Uani 1 1 d . . .
H9A H 0.0466 0.2479 0.0236 0.042 Uiso 1 1 calc R . .
C1 C 0.2527(3) 0.55830(16) 0.40660(14) 0.0559(7) Uani 1 1 d . . .
H1A H 0.2140 0.5064 0.4089 0.067 Uiso 1 1 calc R . .
C2 C 0.2310(3) 0.68550(15) 0.36488(12) 0.0488(6) Uani 1 1 d . . .
H2B H 0.1791 0.7224 0.3382 0.059 Uiso 1 1 calc R . .
C3 C 0.3612(2) 0.70980(13) 0.40226(10) 0.0327(5) Uani 1 1 d . . .
C4 C 0.4341(3) 0.65311(15) 0.44091(11) 0.0472(6) Uani 1 1 d . . .
H4B H 0.5238 0.6674 0.4660 0.057 Uiso 1 1 calc R . .
C6 C 0.4216(3) 0.79191(13) 0.39302(10) 0.0326(5) Uani 1 1 d . . .
C7 C 0.5821(2) 0.90240(12) 0.44002(10) 0.0300(5) Uani 1 1 d . . .
C8 C 0.5682(3) 0.95307(13) 0.38781(10) 0.0358(5) Uani 1 1 d . . .
H8B H 0.5098 0.9383 0.3511 0.043 Uiso 1 1 calc R . .
C9 C 0.6435(3) 1.02548(14) 0.39230(10) 0.0377(5) Uani 1 1 d . . .
H9B H 0.6373 1.0604 0.3578 0.045 Uiso 1 1 calc R . .
C10 C 0.7279(3) 1.04734(13) 0.44664(10) 0.0361(5) Uani 1 1 d . . .
H10A H 0.7788 1.0966 0.4498 0.043 Uiso 1 1 calc R . .
C11 C 0.7349(2) 0.99371(12) 0.49672(9) 0.0288(5) Uani 1 1 d . . .
C12 C 0.8917(2) 1.07798(12) 0.57294(10) 0.0306(5) Uani 1 1 d . . .
C13 C 0.9509(2) 1.08213(12) 0.64084(10) 0.0297(5) Uani 1 1 d . . .
C14 C 1.0763(3) 1.13404(12) 0.65435(10) 0.0344(5) Uani 1 1 d . . .
H14A H 1.1215 1.1604 0.6203 0.041 Uiso 1 1 calc R . .
C15 C 1.0717(3) 1.10991(15) 0.76042(11) 0.0457(6) Uani 1 1 d . . .
H15A H 1.1134 1.1184 0.8016 0.055 Uiso 1 1 calc R . .
C17 C 0.8831(3) 1.04373(13) 0.69150(11) 0.0402(6) Uani 1 1 d . . .
H17A H 0.7968 1.0091 0.6849 0.048 Uiso 1 1 calc R . .
C18 C 0.4698(3) 0.34597(15) 0.40541(12) 0.0503(7) Uani 1 1 d . . .
H18A H 0.4845 0.3843 0.4371 0.060 Uiso 1 1 calc R . .
C19 C 0.4287(3) 0.21699(14) 0.37655(10) 0.0373(5) Uani 1 1 d . . .
H19A H 0.4174 0.1636 0.3877 0.045 Uiso 1 1 calc R . .
C20 C 0.4201(3) 0.23640(13) 0.31195(10) 0.0341(5) Uani 1 1 d . . .
C21 C 0.4438(3) 0.31528(14) 0.29546(11) 0.0398(6) Uani 1 1 d . . .
H21A H 0.4435 0.3306 0.2528 0.048 Uiso 1 1 calc R . .
C23 C 0.3867(3) 0.17204(14) 0.26496(10) 0.0373(5) Uani 1 1 d . . .
C24 C 0.2613(2) 0.14845(12) 0.15796(9) 0.0304(5) Uani 1 1 d . . .
C25 C 0.2930(3) 0.06792(12) 0.15366(10) 0.0354(5) Uani 1 1 d . . .
H25A H 0.3472 0.0407 0.1866 0.043 Uiso 1 1 calc R . .
C26 C 0.2415(3) 0.02968(13) 0.09901(11) 0.0403(6) Uani 1 1 d . . .
H26A H 0.2609 -0.0246 0.0947 0.048 Uiso 1 1 calc R . .
C27 C 0.1623(3) 0.06952(13) 0.05070(11) 0.0375(5) Uani 1 1 d . . .
H27A H 0.1256 0.0435 0.0138 0.045 Uiso 1 1 calc R . .
C28 C 0.1391(3) 0.15005(12) 0.05901(10) 0.0319(5) Uani 1 1 d . . .
C29 C 0.0146(3) 0.17916(13) -0.04763(10) 0.0360(5) Uani 1 1 d . . .
C30 C -0.0205(3) 0.24558(13) -0.09208(9) 0.0322(5) Uani 1 1 d . . .
C31 C -0.1308(3) 0.23541(15) -0.14265(10) 0.0441(6) Uani 1 1 d . . .
H31A H -0.1923 0.1892 -0.1460 0.053 Uiso 1 1 calc R . .
C32 C -0.0532(3) 0.36083(15) -0.18168(11) 0.0459(6) Uani 1 1 d . . .
H32A H -0.0637 0.4001 -0.2129 0.055 Uiso 1 1 calc R . .
C34 C 0.0657(3) 0.31580(12) -0.08954(10) 0.0328(5) Uani 1 1 d . . .
H34A H 0.1367 0.3238 -0.0549 0.039 Uiso 1 1 calc R . .
N1 N 0.1758(3) 0.60916(16) 0.36571(13) 0.0721(7) Uani 1 1 d . . .
C5 C 0.3793(3) 0.57725(14) 0.44357(12) 0.0477(6) Uani 1 1 d . . .
H5A H 0.4287 0.5397 0.4704 0.057 Uiso 1 1 calc R . .
N5 N 1.1366(2) 1.14884(11) 0.71254(9) 0.0383(5) Uani 1 1 d . . .
C16 C 0.9461(3) 1.05783(15) 0.75196(11) 0.0468(6) Uani 1 1 d . . .
H16A H 0.9037 1.0321 0.7869 0.056 Uiso 1 1 calc R . .
N6 N 0.4518(2) 0.26969(12) 0.42337(9) 0.0450(5) Uani 1 1 d . . .
C22 C 0.4677(3) 0.37059(15) 0.34322(11) 0.0486(7) Uani 1 1 d . . .
H22A H 0.4824 0.4241 0.3334 0.058 Uiso 1 1 calc R . .
C33 C -0.1478(3) 0.29453(16) -0.18762(11) 0.0480(6) Uani 1 1 d . . .
H33A H -0.2223 0.2896 -0.2215 0.058 Uiso 1 1 calc R . .
N10 N 0.0539(2) 0.37254(11) -0.13338(9) 0.0400(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 0.0621(11) 0.0473(10) 0.0332(9) 0.0017(8) -0.0137(8) -0.0060(8)
O2 0.0570(10) 0.0325(9) 0.0381(9) 0.0081(7) -0.0069(8) -0.0125(7)
O3 0.0920(14) 0.0407(10) 0.0453(10) -0.0020(8) -0.0265(9) 0.0221(10)
O4 0.0878(14) 0.0334(10) 0.0447(10) -0.0050(8) -0.0223(9) -0.0067(9)
N2 0.0367(10) 0.0316(10) 0.0260(9) 0.0024(8) -0.0031(7) -0.0034(8)
N3 0.0300(9) 0.0284(9) 0.0276(9) 0.0003(7) -0.0011(7) 0.0000(7)
N4 0.0383(10) 0.0254(9) 0.0272(9) 0.0049(7) -0.0045(7) -0.0029(7)
N7 0.0426(10) 0.0265(9) 0.0290(10) -0.0002(8) -0.0074(8) 0.0048(8)
N8 0.0366(9) 0.0259(9) 0.0256(9) -0.0009(7) -0.0029(7) 0.0007(7)
N9 0.0497(11) 0.0258(9) 0.0288(10) -0.0017(8) -0.0064(8) 0.0040(8)
C1 0.0618(18) 0.0399(15) 0.0669(19) -0.0013(14) 0.0144(15) -0.0133(13)
C2 0.0512(15) 0.0482(16) 0.0463(15) -0.0058(12) -0.0082(11) -0.0035(12)
C3 0.0349(11) 0.0356(13) 0.0277(11) -0.0040(9) 0.0000(9) 0.0008(9)
C4 0.0525(15) 0.0507(16) 0.0381(13) 0.0006(11) -0.0056(11) -0.0085(12)
C6 0.0338(11) 0.0358(12) 0.0280(11) -0.0023(9) -0.0010(9) 0.0035(9)
C7 0.0314(11) 0.0313(12) 0.0275(11) 0.0009(9) 0.0010(8) 0.0026(9)
C8 0.0377(12) 0.0393(13) 0.0296(12) 0.0039(10) -0.0074(9) 0.0007(10)
C9 0.0424(13) 0.0407(13) 0.0295(12) 0.0097(10) -0.0023(9) 0.0037(10)
C10 0.0376(12) 0.0321(12) 0.0382(13) 0.0061(10) -0.0033(10) -0.0024(9)
C11 0.0295(10) 0.0281(11) 0.0286(11) 0.0014(9) -0.0005(8) 0.0022(9)
C12 0.0340(11) 0.0262(11) 0.0317(12) 0.0028(9) 0.0006(9) 0.0011(9)
C13 0.0355(11) 0.0240(11) 0.0295(11) -0.0011(9) 0.0011(9) 0.0004(9)
C14 0.0390(12) 0.0309(12) 0.0331(12) 0.0023(9) -0.0017(9) -0.0017(9)
C15 0.0614(16) 0.0433(14) 0.0319(13) -0.0042(11) -0.0037(11) -0.0036(12)
C17 0.0465(13) 0.0348(13) 0.0394(13) -0.0039(10) 0.0047(10) -0.0117(10)
C18 0.0711(18) 0.0410(15) 0.0380(14) -0.0034(11) -0.0086(12) -0.0146(13)
C19 0.0403(12) 0.0359(13) 0.0352(13) 0.0002(10) -0.0040(9) -0.0015(10)
C20 0.0354(11) 0.0355(13) 0.0310(12) 0.0003(10) -0.0062(9) 0.0009(9)
C21 0.0433(13) 0.0429(14) 0.0324(12) 0.0044(10) -0.0073(10) -0.0068(10)
C23 0.0443(13) 0.0353(13) 0.0317(12) 0.0037(10) -0.0072(10) 0.0042(10)
C24 0.0345(11) 0.0299(12) 0.0267(11) 0.0008(9) 0.0000(9) -0.0003(9)
C25 0.0456(13) 0.0273(12) 0.0331(12) 0.0042(9) -0.0022(10) 0.0045(10)
C26 0.0525(14) 0.0253(12) 0.0427(14) -0.0027(10) -0.0031(11) 0.0049(10)
C27 0.0497(14) 0.0285(12) 0.0337(12) -0.0045(9) -0.0057(10) 0.0012(10)
C28 0.0383(12) 0.0288(12) 0.0283(11) 0.0005(9) -0.0013(9) 0.0004(9)
C29 0.0434(12) 0.0328(13) 0.0311(12) -0.0034(10) -0.0069(9) -0.0046(10)
C30 0.0386(12) 0.0325(12) 0.0252(11) -0.0023(9) -0.0013(9) 0.0020(9)
C31 0.0475(14) 0.0508(15) 0.0333(13) -0.0040(11) -0.0088(10) -0.0081(11)
C32 0.0548(15) 0.0506(16) 0.0319(13) 0.0075(11) -0.0050(11) 0.0047(12)
C34 0.0390(12) 0.0308(12) 0.0283(11) -0.0035(9) -0.0037(9) 0.0034(9)
N1 0.0757(18) 0.0648(17) 0.0761(18) -0.0183(15) 0.0046(14) -0.0143(14)
C5 0.0616(16) 0.0375(14) 0.0441(15) 0.0069(11) 0.0019(12) -0.0101(12)
N5 0.0472(11) 0.0352(11) 0.0323(10) 0.0004(8) -0.0034(8) -0.0062(8)
C16 0.0642(17) 0.0468(15) 0.0296(13) 0.0017(11) 0.0048(11) -0.0129(12)
N6 0.0576(13) 0.0448(13) 0.0322(11) -0.0007(9) -0.0052(9) -0.0079(10)
C22 0.0652(17) 0.0348(14) 0.0449(15) 0.0037(11) -0.0097(12) -0.0142(12)
C33 0.0478(14) 0.0599(17) 0.0354(13) 0.0027(12) -0.0116(11) -0.0010(12)
N10 0.0512(12) 0.0367(11) 0.0318(10) 0.0019(9) -0.0031(9) 0.0021(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 C6 1.222(2) . ?
O2 C12 1.219(2) . ?
O3 C23 1.218(3) . ?
O4 C29 1.222(3) . ?
N2 C6 1.364(3) . ?
N2 C7 1.403(3) . ?
N3 C7 1.341(2) . ?
N3 C11 1.342(3) . ?
N4 C12 1.355(3) . ?
N4 C11 1.400(2) . ?
N7 C23 1.356(3) . ?
N7 C24 1.401(3) . ?
N8 C28 1.331(2) . ?
N8 C24 1.334(2) . ?
N9 C29 1.354(3) . ?
N9 C28 1.409(3) . ?
C1 C5 1.325(4) . ?
C1 N1 1.354(4) . ?
C2 N1 1.360(3) . ?
C2 C3 1.377(3) . ?
C3 C4 1.376(3) . ?
C3 C6 1.481(3) . ?
C4 C5 1.353(3) . ?
C7 C8 1.387(3) . ?
C8 C9 1.368(3) . ?
C9 C10 1.367(3) . ?
C10 C11 1.382(3) . ?
C12 C13 1.492(3) . ?
C13 C17 1.380(3) . ?
C13 C14 1.381(3) . ?
C14 N5 1.326(3) . ?
C15 N5 1.328(3) . ?
C15 C16 1.369(3) . ?
C17 C16 1.375(3) . ?
C18 N6 1.343(3) . ?
C18 C22 1.367(3) . ?
C19 N6 1.330(3) . ?
C19 C20 1.392(3) . ?
C20 C21 1.383(3) . ?
C20 C23 1.481(3) . ?
C21 C22 1.374(3) . ?
C24 C25 1.379(3) . ?
C25 C26 1.368(3) . ?
C26 C27 1.364(3) . ?
C27 C28 1.376(3) . ?
C29 C30 1.475(3) . ?
C30 C34 1.379(3) . ?
C30 C31 1.389(3) . ?
C31 C33 1.372(3) . ?
C32 N10 1.340(3) . ?
C32 C33 1.366(3) . ?
C34 N10 1.324(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
C6 N2 C7 126.28(17) . . ?
C7 N3 C11 117.60(17) . . ?
C12 N4 C11 127.54(18) . . ?
C23 N7 C24 127.49(18) . . ?
C28 N8 C24 117.47(17) . . ?
C29 N9 C28 127.63(18) . . ?
C5 C1 N1 124.6(2) . . ?
N1 C2 C3 122.1(2) . . ?
C4 C3 C2 116.9(2) . . ?
C4 C3 C6 125.07(19) . . ?
C2 C3 C6 117.7(2) . . ?
C5 C4 C3 122.1(2) . . ?
O1 C6 N2 123.4(2) . . ?
O1 C6 C3 118.05(19) . . ?
N2 C6 C3 118.54(18) . . ?
N3 C7 C8 122.90(19) . . ?
N3 C7 N2 114.01(17) . . ?
C8 C7 N2 123.09(18) . . ?
C9 C8 C7 117.6(2) . . ?
C10 C9 C8 121.1(2) . . ?
C9 C10 C11 117.7(2) . . ?
N3 C11 C10 123.07(19) . . ?
N3 C11 N4 113.91(17) . . ?
C10 C11 N4 123.03(19) . . ?
O2 C12 N4 124.24(19) . . ?
O2 C12 C13 119.73(19) . . ?
N4 C12 C13 116.03(18) . . ?
C17 C13 C14 117.6(2) . . ?
C17 C13 C12 125.6(2) . . ?
C14 C13 C12 116.57(19) . . ?
N5 C14 C13 124.4(2) . . ?
N5 C15 C16 123.0(2) . . ?
C16 C17 C13 118.4(2) . . ?
N6 C18 C22 123.9(2) . . ?
N6 C19 C20 124.3(2) . . ?
C21 C20 C19 117.6(2) . . ?
C21 C20 C23 123.75(19) . . ?
C19 C20 C23 118.6(2) . . ?
C22 C21 C20 118.8(2) . . ?
O3 C23 N7 124.2(2) . . ?
O3 C23 C20 120.89(19) . . ?
N7 C23 C20 114.89(19) . . ?
N8 C24 C25 123.08(19) . . ?
N8 C24 N7 113.07(17) . . ?
C25 C24 N7 123.84(18) . . ?
C26 C25 C24 117.27(19) . . ?
C27 C26 C25 121.4(2) . . ?
C26 C27 C28 116.9(2) . . ?
N8 C28 C27 123.79(19) . . ?
N8 C28 N9 112.92(17) . . ?
C27 C28 N9 123.28(19) . . ?
O4 C29 N9 123.8(2) . . ?
O4 C29 C30 119.62(18) . . ?
N9 C29 C30 116.52(19) . . ?
C34 C30 C31 117.6(2) . . ?
C34 C30 C29 121.92(18) . . ?
C31 C30 C29 120.1(2) . . ?
C33 C31 C30 119.0(2) . . ?
N10 C32 C33 123.7(2) . . ?
N10 C34 C30 124.10(19) . . ?
C1 N1 C2 116.6(2) . . ?
C1 C5 C4 117.6(2) . . ?
C14 N5 C15 116.9(2) . . ?
C15 C16 C17 119.6(2) . . ?
C19 N6 C18 116.1(2) . . ?
C18 C22 C21 119.2(2) . . ?
C32 C33 C31 118.7(2) . . ?
C34 N10 C32 116.8(2) . . ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 28.40
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.350
_refine_diff_density_min -0.380
_refine_diff_density_rms 0.055