# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2010


data_global
#TrackingRef '- Crystal Data.cif.cif'

_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
#==============================================================================
_audit_creation_method           SHELXL-97

_publ_contact_author_name        'Weisheng Liu'
_publ_contact_author_address     
;
Key Laboratory of Nonferrous Metal Chemistry and Resources.
Utilization of Gansu Province and State Key Laboratory of
Applied Organic Chemistry, College of Chemistry and Chemical
Engineering, Lanzhou University,
Lanzhou 730000, P. R. China.
;
_publ_contact_author_email       liuws@lzu.edu.cn
_publ_contact_author_fax         86-0931-8912582
_publ_contact_author_phone       86-0931-8915151
#==============================================================================

# TITLE AND AUTHOR LIST

_publ_section_title              
;
A Selective, Cell-Permeable Fluorescent Probe for Al3+ in Living Cells
;

loop_
_publ_author_name
_publ_author_address

'Lina Wang'
;
Key Laboratory of Nonferrous Metal Chemistry and Resources.
Utilization of Gansu Province and State Key Laboratory of
Applied Organic Chemistry, College of Chemistry and Chemical
Engineering, Lanzhou University,
Lanzhou 730000, P. R. China.
;
'Weisheng Liu'
;
Key Laboratory of Nonferrous Metal Chemistry and Resources.
Utilization of Gansu Province and State Key Laboratory of
Applied Organic Chemistry, College of Chemistry and Chemical
Engineering, Lanzhou University,
Lanzhou 730000, P. R. China.
;
'Wenwu Qin'
;
Key Laboratory of Nonferrous Metal Chemistry and Resources.
Utilization of Gansu Province and State Key Laboratory of
Applied Organic Chemistry, College of Chemistry and Chemical
Engineering, Lanzhou University,
Lanzhou 730000, P. R. China.
;
'Xiaoliang Tang'
;
Key Laboratory of Nonferrous Metal Chemistry and Resources.
Utilization of Gansu Province and State Key Laboratory of
Applied Organic Chemistry, College of Chemistry and Chemical
Engineering, Lanzhou University,
Lanzhou 730000, P. R. China.
;
'Qingfeng Teng'
;
College of Chemistry and Chemical
Engineering, Lanzhou University,
Lanzhou 730000, P. R. China.
;
;
Xiaojun Yao
;
;
College of Chemistry and Chemical
Engineering, Lanzhou University,
Lanzhou 730000, P. R. China.
;
#==============================================================================

#data_muru
#TrackingRef '- Crystal Data.cif.cif'

data_cc
#TrackingRef '- Crystal Data.cif.cif'

_database_code_depnum_ccdc_archive 'CCDC 746902'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C15 H10 N2 O2'

_chemical_formula_weight         250.25

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   Cc

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                   12.022(5)

_cell_length_b                   11.403(5)

_cell_length_c                   17.406(10)

_cell_angle_alpha                90.00

_cell_angle_beta                 95.445(11)

_cell_angle_gamma                90.00

_cell_volume                     2375(2)

_cell_formula_units_Z            8

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    1229

_cell_measurement_theta_min      0.00

_cell_measurement_theta_max      0.00

_exptl_crystal_description       sheet

_exptl_crystal_colour            none

_exptl_crystal_size_max          0.26

_exptl_crystal_size_mid          0.25

_exptl_crystal_size_min          0.15

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.400

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             1040

_exptl_absorpt_coefficient_mu    0.095

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9312

_exptl_absorpt_correction_T_max  0.9501

_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      293(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            5422

_diffrn_reflns_av_R_equivalents  0.0433

_diffrn_reflns_av_sigmaI/netI    0.0522

_diffrn_reflns_limit_h_min       -11

_diffrn_reflns_limit_h_max       13

_diffrn_reflns_limit_k_min       -13

_diffrn_reflns_limit_k_max       13

_diffrn_reflns_limit_l_min       -17

_diffrn_reflns_limit_l_max       20

_diffrn_reflns_theta_min         2.35

_diffrn_reflns_theta_max         24.26

_reflns_number_total             2585

_reflns_number_gt                1787

_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^)+(0.1150P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   2(3)

_refine_ls_number_reflns         2585

_refine_ls_number_parameters     343

_refine_ls_number_restraints     2

_refine_ls_R_factor_all          0.1002

_refine_ls_R_factor_gt           0.0703

_refine_ls_wR_factor_ref         0.1826

_refine_ls_wR_factor_gt          0.1604

_refine_ls_goodness_of_fit_ref   1.016

_refine_ls_restrained_S_all      1.016

_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
C1 C 0.4347(7) 0.9762(6) 0.3219(4) 0.044(2) Uani 1 1 d . . .
C2 C 0.3605(7) 1.0620(7) 0.3440(4) 0.057(2) Uani 1 1 d . . .
H2 H 0.2880 1.0645 0.3201 0.068 Uiso 1 1 calc R . .
C3 C 0.3915(8) 1.1387(6) 0.3979(5) 0.061(2) Uani 1 1 d . . .
H3 H 0.3421 1.1968 0.4104 0.073 Uiso 1 1 calc R . .
C4 C 0.5017(8) 1.1330(7) 0.4375(5) 0.058(2) Uani 1 1 d . . .
H4 H 0.5241 1.1838 0.4778 0.070 Uiso 1 1 calc R . .
C5 C 0.5705(7) 1.0518(6) 0.4141(4) 0.049(2) Uani 1 1 d . . .
H5 H 0.6436 1.0503 0.4370 0.058 Uiso 1 1 calc R . .
C6 C 0.5396(6) 0.9694(6) 0.3574(4) 0.0390(17) Uani 1 1 d . . .
C7 C 0.6132(6) 0.8746(5) 0.3399(4) 0.0428(16) Uani 1 1 d . . .
C8 C 0.5990(6) 0.6490(5) 0.2021(4) 0.0526(18) Uani 1 1 d . . .
H8 H 0.6400 0.5830 0.1910 0.063 Uiso 1 1 calc R . .
C9 C 0.5028(7) 0.6726(7) 0.1532(4) 0.047(2) Uani 1 1 d . . .
C10 C 0.4617(8) 0.5920(7) 0.0930(4) 0.058(2) Uani 1 1 d . . .
H10 H 0.5017 0.5240 0.0849 0.070 Uiso 1 1 calc R . .
C11 C 0.3675(8) 0.6137(7) 0.0490(5) 0.062(3) Uani 1 1 d . . .
H11 H 0.3428 0.5600 0.0110 0.074 Uiso 1 1 calc R . .
C12 C 0.3033(7) 0.7168(7) 0.0585(4) 0.057(2) Uani 1 1 d . . .
H12 H 0.2372 0.7308 0.0276 0.069 Uiso 1 1 calc R . .
C13 C 0.3429(7) 0.7959(8) 0.1157(4) 0.056(2) Uani 1 1 d . . .
H13 H 0.3027 0.8641 0.1230 0.067 Uiso 1 1 calc R . .
C14 C 0.4435(6) 0.7741(7) 0.1629(4) 0.0413(18) Uani 1 1 d . . .
C15 C 0.4848(6) 0.8576(5) 0.2216(4) 0.0380(17) Uani 1 1 d . . .
H15 H 0.5138 0.9261 0.1959 0.046 Uiso 1 1 calc R . .
C16 C 0.4508(6) 0.2713(7) 0.1626(4) 0.0444(19) Uani 1 1 d . . .
C17 C 0.5259(8) 0.1890(7) 0.1425(5) 0.065(3) Uani 1 1 d . . .
H17 H 0.5979 0.1852 0.1672 0.077 Uiso 1 1 calc R . .
C18 C 0.4895(9) 0.1099(7) 0.0825(5) 0.070(3) Uani 1 1 d . . .
H18 H 0.5394 0.0542 0.0672 0.084 Uiso 1 1 calc R . .
C19 C 0.3851(9) 0.1127(7) 0.0470(5) 0.063(3) Uani 1 1 d . . .
H19 H 0.3638 0.0571 0.0094 0.075 Uiso 1 1 calc R . .
C20 C 0.3067(8) 0.1990(7) 0.0658(4) 0.060(2) Uani 1 1 d . . .
H20 H 0.2356 0.2038 0.0398 0.072 Uiso 1 1 calc R . .
C21 C 0.3428(6) 0.2770(6) 0.1261(4) 0.0457(19) Uani 1 1 d . . .
C22 C 0.2661(6) 0.3720(5) 0.1452(4) 0.0446(16) Uani 1 1 d . . .
C23 C 0.2801(7) 0.5950(6) 0.2837(4) 0.0571(19) Uani 1 1 d . . .
H23 H 0.2382 0.6606 0.2943 0.069 Uiso 1 1 calc R . .
C24 C 0.3807(7) 0.5726(7) 0.3372(4) 0.052(2) Uani 1 1 d . . .
C25 C 0.4166(9) 0.6487(7) 0.3928(5) 0.067(3) Uani 1 1 d . . .
H25 H 0.3761 0.7165 0.4005 0.080 Uiso 1 1 calc R . .
C26 C 0.5166(10) 0.6248(9) 0.4396(5) 0.067(3) Uani 1 1 d . . .
H26 H 0.5420 0.6740 0.4801 0.081 Uiso 1 1 calc R . .
C27 C 0.5716(8) 0.5307(10) 0.4235(5) 0.079(3) Uani 1 1 d . . .
H27 H 0.6394 0.5172 0.4525 0.095 Uiso 1 1 calc R . .
C28 C 0.5379(8) 0.4493(8) 0.3670(5) 0.060(2) Uani 1 1 d . . .
H28 H 0.5799 0.3825 0.3596 0.072 Uiso 1 1 calc R . .
C29 C 0.4418(7) 0.4709(6) 0.3232(4) 0.044(2) Uani 1 1 d . . .
C30 C 0.3937(6) 0.3848(5) 0.2625(4) 0.0343(16) Uani 1 1 d . . .
H30 H 0.3643 0.3163 0.2879 0.041 Uiso 1 1 calc R . .
N1 N 0.5756(5) 0.8091(4) 0.2758(3) 0.0388(12) Uani 1 1 d . . .
N2 N 0.6360(5) 0.7101(4) 0.2611(3) 0.0508(14) Uani 1 1 d . . .
N3 N 0.3053(5) 0.4365(4) 0.2101(3) 0.0455(13) Uani 1 1 d . . .
N4 N 0.2440(5) 0.5353(4) 0.2249(3) 0.0516(14) Uani 1 1 d . . .
O1 O 0.3951(4) 0.8951(4) 0.2641(3) 0.0490(14) Uani 1 1 d . . .
O2 O 0.7006(5) 0.8515(4) 0.3796(3) 0.0577(13) Uani 1 1 d . . .
O3 O 0.4841(4) 0.3493(4) 0.2197(3) 0.0525(14) Uani 1 1 d . . .
O4 O 0.1798(5) 0.3958(4) 0.1050(3) 0.0613(13) 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
C1 0.059(6) 0.041(4) 0.030(4) 0.013(3) 0.003(4) 0.010(4)
C2 0.055(5) 0.080(5) 0.035(4) 0.019(4) 0.006(3) 0.042(5)
C3 0.079(7) 0.052(4) 0.054(5) 0.005(4) 0.014(4) 0.029(4)
C4 0.079(7) 0.057(5) 0.040(4) -0.002(4) 0.014(5) -0.006(5)
C5 0.038(4) 0.051(4) 0.056(5) 0.012(4) 0.000(4) -0.005(3)
C6 0.040(4) 0.042(3) 0.036(4) 0.005(3) 0.007(3) 0.010(3)
C7 0.031(4) 0.054(3) 0.043(4) 0.014(3) -0.003(3) 0.006(3)
C8 0.064(5) 0.045(4) 0.049(4) -0.004(3) 0.009(3) 0.007(4)
C9 0.052(5) 0.055(4) 0.035(4) 0.006(3) 0.004(3) -0.004(4)
C10 0.066(6) 0.058(4) 0.049(5) 0.002(3) -0.004(4) -0.014(4)
C11 0.069(7) 0.063(5) 0.054(5) -0.006(4) 0.007(5) -0.017(5)
C12 0.051(5) 0.095(6) 0.024(3) 0.005(4) -0.008(3) -0.006(4)
C13 0.042(5) 0.079(5) 0.045(5) 0.007(4) 0.002(4) -0.004(4)
C14 0.026(4) 0.061(4) 0.037(4) 0.008(4) 0.003(3) 0.000(4)
C15 0.024(4) 0.054(4) 0.036(4) 0.007(3) 0.005(3) 0.005(3)
C16 0.039(5) 0.056(4) 0.039(4) 0.005(3) 0.008(3) 0.008(4)
C17 0.053(6) 0.069(5) 0.070(5) -0.003(4) 0.001(4) 0.024(5)
C18 0.097(8) 0.059(5) 0.057(5) 0.004(4) 0.022(5) 0.037(5)
C19 0.078(7) 0.043(4) 0.067(6) -0.007(4) 0.009(5) 0.021(4)
C20 0.062(6) 0.063(4) 0.054(5) -0.014(4) 0.003(4) 0.010(4)
C21 0.043(5) 0.048(4) 0.045(4) -0.003(3) -0.001(3) 0.004(3)
C22 0.041(5) 0.052(4) 0.041(4) 0.005(3) 0.005(3) -0.001(3)
C23 0.062(5) 0.055(4) 0.055(4) -0.002(3) 0.008(4) 0.005(4)
C24 0.060(6) 0.055(4) 0.041(4) 0.003(3) 0.002(4) -0.006(4)
C25 0.092(8) 0.054(5) 0.056(5) 0.005(4) 0.013(5) -0.004(5)
C26 0.082(8) 0.074(6) 0.046(5) -0.005(4) 0.003(5) -0.031(6)
C27 0.044(6) 0.116(8) 0.076(7) -0.003(6) -0.007(5) -0.033(6)
C28 0.055(6) 0.075(5) 0.050(5) -0.001(4) 0.003(4) 0.002(5)
C29 0.057(6) 0.041(4) 0.036(4) 0.009(3) 0.005(4) -0.007(4)
C30 0.034(4) 0.035(3) 0.034(4) 0.007(3) 0.003(3) 0.006(3)
N1 0.030(3) 0.047(3) 0.038(3) 0.005(2) -0.002(2) 0.006(2)
N2 0.049(4) 0.042(3) 0.060(4) 0.003(2) 0.004(3) 0.012(2)
N3 0.045(4) 0.044(3) 0.048(3) 0.004(2) 0.007(3) 0.007(2)
N4 0.050(4) 0.054(3) 0.051(3) 0.004(2) 0.001(3) 0.014(3)
O1 0.035(3) 0.064(3) 0.046(3) 0.001(3) -0.003(3) 0.015(3)
O2 0.046(3) 0.066(3) 0.058(3) 0.000(2) -0.012(2) 0.016(2)
O3 0.035(3) 0.070(3) 0.052(3) 0.002(3) 0.002(3) 0.010(3)
O4 0.041(3) 0.077(3) 0.064(3) -0.004(2) -0.009(2) 0.015(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
C1 C6 1.353(11) . ?
C1 C2 1.403(10) . ?
C1 O1 1.416(8) . ?
C2 C3 1.309(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.436(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.330(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.448(9) . ?
C7 O2 1.229(8) . ?
C7 N1 1.383(8) . ?
C8 N2 1.285(7) . ?
C8 C9 1.396(11) . ?
C8 H8 0.9300 . ?
C9 C14 1.378(10) . ?
C9 C10 1.446(11) . ?
C10 C11 1.328(12) . ?
C10 H10 0.9300 . ?
C11 C12 1.425(11) . ?
C11 H11 0.9300 . ?
C12 C13 1.393(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.419(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.449(9) . ?
C15 O1 1.430(6) . ?
C15 N1 1.481(10) . ?
C15 H15 0.9800 . ?
C16 O3 1.366(8) . ?
C16 C17 1.370(11) . ?
C16 C21 1.392(11) . ?
C17 C18 1.417(12) . ?
C17 H17 0.9300 . ?
C18 C19 1.346(14) . ?
C18 H18 0.9300 . ?
C19 C20 1.422(11) . ?
C19 H19 0.9300 . ?
C20 C21 1.412(10) . ?
C20 H20 0.9300 . ?
C21 C22 1.481(10) . ?
C22 O4 1.226(8) . ?
C22 N3 1.392(8) . ?
C23 N4 1.270(8) . ?
C23 C24 1.477(12) . ?
C23 H23 0.9300 . ?
C24 C25 1.340(12) . ?
C24 C29 1.406(10) . ?
C25 C26 1.413(14) . ?
C25 H25 0.9300 . ?
C26 C27 1.305(13) . ?
C26 H26 0.9300 . ?
C27 C28 1.385(12) . ?
C27 H27 0.9300 . ?
C28 C29 1.345(13) . ?
C28 H28 0.9300 . ?
C29 C30 1.515(9) . ?
C30 O3 1.433(6) . ?
C30 N3 1.458(10) . ?
C30 H30 0.9800 . ?
N1 N2 1.379(6) . ?
N3 N4 1.384(6) . ?

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 C1 C2 120.3(7) . . ?
C6 C1 O1 121.6(7) . . ?
C2 C1 O1 118.1(7) . . ?
C3 C2 C1 121.1(8) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.0(8) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 117.2(8) . . ?
C5 C4 H4 121.4 . . ?
C3 C4 H4 121.4 . . ?
C4 C5 C6 123.8(8) . . ?
C4 C5 H5 118.1 . . ?
C6 C5 H5 118.1 . . ?
C1 C6 C5 117.5(7) . . ?
C1 C6 C7 120.6(7) . . ?
C5 C6 C7 121.8(7) . . ?
O2 C7 N1 122.3(6) . . ?
O2 C7 C6 123.3(6) . . ?
N1 C7 C6 114.4(6) . . ?
N2 C8 C9 125.9(6) . . ?
N2 C8 H8 117.0 . . ?
C9 C8 H8 117.0 . . ?
C14 C9 C8 119.7(7) . . ?
C14 C9 C10 118.5(7) . . ?
C8 C9 C10 121.8(8) . . ?
C11 C10 C9 120.9(9) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 121.9(8) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C13 C12 C11 117.7(7) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C12 C13 C14 121.0(8) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C9 C14 C13 119.9(7) . . ?
C9 C14 C15 119.4(6) . . ?
C13 C14 C15 120.6(7) . . ?
O1 C15 C14 109.6(5) . . ?
O1 C15 N1 109.1(5) . . ?
C14 C15 N1 112.7(5) . . ?
O1 C15 H15 108.4 . . ?
C14 C15 H15 108.4 . . ?
N1 C15 H15 108.4 . . ?
O3 C16 C17 118.5(7) . . ?
O3 C16 C21 119.9(7) . . ?
C17 C16 C21 121.6(8) . . ?
C16 C17 C18 117.3(8) . . ?
C16 C17 H17 121.3 . . ?
C18 C17 H17 121.3 . . ?
C19 C18 C17 122.1(8) . . ?
C19 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
C18 C19 C20 121.4(9) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C21 C20 C19 116.3(8) . . ?
C21 C20 H20 121.9 . . ?
C19 C20 H20 121.9 . . ?
C16 C21 C20 121.2(7) . . ?
C16 C21 C22 120.3(7) . . ?
C20 C21 C22 118.3(7) . . ?
O4 C22 N3 123.3(6) . . ?
O4 C22 C21 123.1(6) . . ?
N3 C22 C21 113.6(6) . . ?
N4 C23 C24 127.7(7) . . ?
N4 C23 H23 116.1 . . ?
C24 C23 H23 116.1 . . ?
C25 C24 C29 121.4(8) . . ?
C25 C24 C23 122.1(8) . . ?
C29 C24 C23 116.3(7) . . ?
C24 C25 C26 119.3(9) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C27 C26 C25 117.1(9) . . ?
C27 C26 H26 121.4 . . ?
C25 C26 H26 121.4 . . ?
C26 C27 C28 125.7(9) . . ?
C26 C27 H27 117.2 . . ?
C28 C27 H27 117.2 . . ?
C29 C28 C27 117.3(9) . . ?
C29 C28 H28 121.4 . . ?
C27 C28 H28 121.4 . . ?
C28 C29 C24 119.1(8) . . ?
C28 C29 C30 121.8(7) . . ?
C24 C29 C30 118.9(7) . . ?
O3 C30 N3 109.4(5) . . ?
O3 C30 C29 106.7(6) . . ?
N3 C30 C29 112.4(5) . . ?
O3 C30 H30 109.4 . . ?
N3 C30 H30 109.4 . . ?
C29 C30 H30 109.4 . . ?
N2 N1 C7 117.0(5) . . ?
N2 N1 C15 123.8(5) . . ?
C7 N1 C15 118.6(5) . . ?
C8 N2 N1 116.3(5) . . ?
N4 N3 C22 115.9(5) . . ?
N4 N3 C30 125.5(5) . . ?
C22 N3 C30 117.7(5) . . ?
C23 N4 N3 116.1(5) . . ?
C1 O1 C15 110.1(5) . . ?
C16 O3 C30 112.2(5) . . ?

loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag
C6 C1 C2 C3 1.7(11) . . . . ?
O1 C1 C2 C3 179.1(7) . . . . ?
C1 C2 C3 C4 -2.5(12) . . . . ?
C2 C3 C4 C5 3.6(12) . . . . ?
C3 C4 C5 C6 -3.9(12) . . . . ?
C2 C1 C6 C5 -1.8(11) . . . . ?
O1 C1 C6 C5 -179.2(6) . . . . ?
C2 C1 C6 C7 174.2(6) . . . . ?
O1 C1 C6 C7 -3.1(11) . . . . ?
C4 C5 C6 C1 3.1(12) . . . . ?
C4 C5 C6 C7 -172.9(7) . . . . ?
C1 C6 C7 O2 -166.3(7) . . . . ?
C5 C6 C7 O2 9.6(10) . . . . ?
C1 C6 C7 N1 11.8(9) . . . . ?
C5 C6 C7 N1 -172.4(6) . . . . ?
N2 C8 C9 C14 5.2(11) . . . . ?
N2 C8 C9 C10 -173.5(6) . . . . ?
C14 C9 C10 C11 -1.6(12) . . . . ?
C8 C9 C10 C11 177.2(8) . . . . ?
C9 C10 C11 C12 0.5(13) . . . . ?
C10 C11 C12 C13 0.4(12) . . . . ?
C11 C12 C13 C14 -0.3(11) . . . . ?
C8 C9 C14 C13 -177.1(7) . . . . ?
C10 C9 C14 C13 1.7(10) . . . . ?
C8 C9 C14 C15 2.9(10) . . . . ?
C10 C9 C14 C15 -178.3(6) . . . . ?
C12 C13 C14 C9 -0.8(11) . . . . ?
C12 C13 C14 C15 179.2(6) . . . . ?
C9 C14 C15 O1 -134.4(6) . . . . ?
C13 C14 C15 O1 45.6(8) . . . . ?
C9 C14 C15 N1 -12.6(9) . . . . ?
C13 C14 C15 N1 167.4(7) . . . . ?
O3 C16 C17 C18 -179.4(7) . . . . ?
C21 C16 C17 C18 0.4(12) . . . . ?
C16 C17 C18 C19 -1.2(14) . . . . ?
C17 C18 C19 C20 2.6(15) . . . . ?
C18 C19 C20 C21 -3.1(13) . . . . ?
O3 C16 C21 C20 178.7(7) . . . . ?
C17 C16 C21 C20 -1.0(13) . . . . ?
O3 C16 C21 C22 4.0(11) . . . . ?
C17 C16 C21 C22 -175.7(7) . . . . ?
C19 C20 C21 C16 2.3(12) . . . . ?
C19 C20 C21 C22 177.1(7) . . . . ?
C16 C21 C22 O4 164.8(7) . . . . ?
C20 C21 C22 O4 -10.1(11) . . . . ?
C16 C21 C22 N3 -11.0(9) . . . . ?
C20 C21 C22 N3 174.1(6) . . . . ?
N4 C23 C24 C25 173.1(8) . . . . ?
N4 C23 C24 C29 -2.5(11) . . . . ?
C29 C24 C25 C26 -1.6(13) . . . . ?
C23 C24 C25 C26 -176.9(8) . . . . ?
C24 C25 C26 C27 2.9(14) . . . . ?
C25 C26 C27 C28 -3.3(15) . . . . ?
C26 C27 C28 C29 2.3(15) . . . . ?
C27 C28 C29 C24 -0.7(12) . . . . ?
C27 C28 C29 C30 -176.7(7) . . . . ?
C25 C24 C29 C28 0.5(12) . . . . ?
C23 C24 C29 C28 176.0(8) . . . . ?
C25 C24 C29 C30 176.6(8) . . . . ?
C23 C24 C29 C30 -7.8(10) . . . . ?
C28 C29 C30 O3 -46.4(9) . . . . ?
C24 C29 C30 O3 137.6(6) . . . . ?
C28 C29 C30 N3 -166.4(7) . . . . ?
C24 C29 C30 N3 17.6(9) . . . . ?
O2 C7 N1 N2 4.9(8) . . . . ?
C6 C7 N1 N2 -173.2(5) . . . . ?
O2 C7 N1 C15 -166.3(6) . . . . ?
C6 C7 N1 C15 15.6(8) . . . . ?
O1 C15 N1 N2 139.2(5) . . . . ?
C14 C15 N1 N2 17.2(8) . . . . ?
O1 C15 N1 C7 -50.3(7) . . . . ?
C14 C15 N1 C7 -172.3(5) . . . . ?
C9 C8 N2 N1 -1.4(9) . . . . ?
C7 N1 N2 C8 178.9(6) . . . . ?
C15 N1 N2 C8 -10.5(8) . . . . ?
O4 C22 N3 N4 -3.6(8) . . . . ?
C21 C22 N3 N4 172.2(5) . . . . ?
O4 C22 N3 C30 166.3(7) . . . . ?
C21 C22 N3 C30 -17.9(8) . . . . ?
O3 C30 N3 N4 -138.8(5) . . . . ?
C29 C30 N3 N4 -20.4(9) . . . . ?
O3 C30 N3 C22 52.3(7) . . . . ?
C29 C30 N3 C22 170.7(5) . . . . ?
C24 C23 N4 N3 1.2(10) . . . . ?
C22 N3 N4 C23 -179.4(5) . . . . ?
C30 N3 N4 C23 11.6(9) . . . . ?
C6 C1 O1 C15 -32.3(8) . . . . ?
C2 C1 O1 C15 150.3(5) . . . . ?
C14 C15 O1 C1 179.6(6) . . . . ?
N1 C15 O1 C1 55.7(6) . . . . ?
C17 C16 O3 C30 -148.9(7) . . . . ?
C21 C16 O3 C30 31.4(8) . . . . ?
N3 C30 O3 C16 -57.9(6) . . . . ?
C29 C30 O3 C16 -179.7(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.985

_diffrn_reflns_theta_full        24.26

_diffrn_measured_fraction_theta_full 0.985

_refine_diff_density_max         0.550

_refine_diff_density_min         -0.211

_refine_diff_density_rms         0.072