

data_global

data_3_120K_new
#TrackingRef 'web_deposit_cif_file_0_SantiagoGarcia-Granda_1365518175.3-120K_806879_new.cif'

#CCDC-806879

_audit_update_record             
;
2013-04-08 # Formatted by publCIF
;
_audit_creation_date             2013-04-03
_audit_creation_method           
;
Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 N4 O4'
_chemical_formula_sum            'C13 H8 N4 O4'
_chemical_formula_weight         284.23
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H8 N4 O4 '
_chemical_oxdiff_usercomment     'Medida a RT - GMN10040'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   7.0459(2)
_cell_length_b                   11.048(3)
_cell_length_c                   15.4564(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1203.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2412
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      70.2804
_cell_measurement_theta_min      3.9981
_exptl_absorpt_coefficient_mu    1.025
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET)
(compiled Dec 8 2009,17:31:18)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.1436
_exptl_crystal_size_mid          0.0829
_exptl_crystal_size_min          0.0622
_exptl_special_details           ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4652
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         70.41
_diffrn_reflns_theta_min         4.92
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean 10.2673
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega -96.00 -28.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 -37.0000 30.0000 68

#__ type_ start__ end____ width___ exp.time_
2 omega -96.00 -12.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 125.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
3 omega 99.00 126.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -45.0000 150.0000 27

#__ type_ start__ end____ width___ exp.time_
4 omega 73.00 108.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 76.0000 -117.0000 35

#__ type_ start__ end____ width___ exp.time_
5 omega 136.00 167.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 76.0000 -117.0000 31

#__ type_ start__ end____ width___ exp.time_
6 omega 28.00 114.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -75.0000 52.0000 86

#__ type_ start__ end____ width___ exp.time_
7 omega 110.00 177.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 111.0000 60.0000 67

#__ type_ start__ end____ width___ exp.time_
8 omega 76.00 167.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 45.0000 -120.0000 91

#__ type_ start__ end____ width___ exp.time_
9 omega 94.00 120.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -45.0000 60.0000 26

#__ type_ start__ end____ width___ exp.time_
10 omega 113.00 177.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 111.0000 0.0000 64

#__ type_ start__ end____ width___ exp.time_
11 omega -120.00 -95.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 -77.0000 -180.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1816885000
_diffrn_orient_matrix_UB_12      0.0589204000
_diffrn_orient_matrix_UB_13      0.0362603000
_diffrn_orient_matrix_UB_21      -0.0039548000
_diffrn_orient_matrix_UB_22      -0.0939678000
_diffrn_orient_matrix_UB_23      0.0736830000
_diffrn_orient_matrix_UB_31      0.1215767000
_diffrn_orient_matrix_UB_32      0.0845444000
_diffrn_orient_matrix_UB_33      0.0564648000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2051
_reflns_number_total             2258
_reflns_odcompleteness_completeness 99.24
_reflns_odcompleteness_iscentric 0
_reflns_odcompleteness_theta     68.13
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET)
(compiled Dec 8 2009,17:31:18)
;
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET)
(compiled Dec 8 2009,17:31:18)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET)
(compiled Dec 8 2009,17:31:18)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0365P)²+0.0293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0796
_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 1.0666(3) 0.61895(19) 0.68586(12) 0.0316(4) Uani 1 1 d . . .
H1 H 1.1078 0.6119 0.7442 0.038 Uiso 1 1 calc R . .
C2 C 1.0336(3) 0.73177(17) 0.64367(11) 0.0267(4) Uani 1 1 d . . .
C3 C 1.0498(3) 0.85380(18) 0.66728(12) 0.0297(4) Uani 1 1 d . . .
H3 H 1.0878 0.8764 0.7240 0.036 Uiso 1 1 calc R . .
C4 C 1.0088(3) 0.93993(18) 0.60551(13) 0.0306(4) Uani 1 1 d . . .
H4 H 1.0203 1.0232 0.6198 0.037 Uiso 1 1 calc R . .
C5 C 0.9502(3) 0.90694(17) 0.52167(13) 0.0283(4) Uani 1 1 d . . .
H5 H 0.9223 0.9686 0.4808 0.034 Uiso 1 1 calc R . .
C6 C 0.9322(3) 0.78700(16) 0.49735(12) 0.0243(4) Uani 1 1 d . . .
H6 H 0.8916 0.7648 0.4409 0.029 Uiso 1 1 calc R . .
C7 C 0.9765(3) 0.70005(16) 0.55996(11) 0.0227(4) Uani 1 1 d . . .
N2 N 1.0338(3) 0.52606(15) 0.63539(10) 0.0296(4) Uani 1 1 d . . .
N1 N 0.9771(3) 0.57463(13) 0.55720(9) 0.0243(3) Uani 1 1 d . . .
C8 C 0.9493(3) 0.49698(15) 0.48718(11) 0.0230(4) Uani 1 1 d . . .
C9 C 0.8745(3) 0.38014(17) 0.49785(11) 0.0250(4) Uani 1 1 d . . .
N3 N 0.8042(3) 0.33725(14) 0.58211(10) 0.0281(4) Uani 1 1 d . . .
O1 O 0.6862(2) 0.39885(13) 0.61970(9) 0.0334(3) Uani 1 1 d . . .
O2 O 0.8628(3) 0.23907(13) 0.60778(10) 0.0410(4) Uani 1 1 d . . .
C10 C 0.8556(3) 0.30021(17) 0.42993(13) 0.0270(4) Uani 1 1 d . . .
H10 H 0.8077 0.2207 0.4386 0.032 Uiso 1 1 calc R . .
C11 C 0.9090(3) 0.34013(17) 0.34849(12) 0.0256(4) Uani 1 1 d . . .
N4 N 0.8902(3) 0.25640(15) 0.27550(11) 0.0306(4) Uani 1 1 d . . .
O3 O 0.8172(2) 0.15755(13) 0.28867(10) 0.0359(3) Uani 1 1 d . . .
O4 O 0.9487(3) 0.28999(14) 0.20487(10) 0.0478(4) Uani 1 1 d . . .
C12 C 0.9829(3) 0.45436(16) 0.33435(12) 0.0255(4) Uani 1 1 d . . .
H12 H 1.0179 0.4793 0.2777 0.031 Uiso 1 1 calc R . .
C13 C 1.0052(3) 0.53177(16) 0.40404(11) 0.0252(4) Uani 1 1 d . . .
H13 H 1.0593 0.6096 0.3952 0.030 Uiso 1 1 calc R . .


_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 C2 1.426(3) . ?
C1 N2 1.310(3) . ?
C2 C3 1.401(3) . ?
C2 C7 1.399(3) . ?
C3 C4 1.379(3) . ?
C4 C5 1.408(3) . ?
C5 C6 1.383(3) . ?
C6 C7 1.399(3) . ?
C7 N1 1.386(2) . ?
N2 N1 1.381(2) . ?
N1 C8 1.395(2) . ?
C8 C9 1.404(3) . ?
C8 C13 1.398(3) . ?
C9 N3 1.472(2) . ?
C9 C10 1.378(3) . ?
N3 O1 1.222(2) . ?
N3 O2 1.226(2) . ?
C10 C11 1.386(3) . ?
C11 N4 1.465(2) . ?
C11 C12 1.383(3) . ?
N4 O3 1.224(2) . ?
N4 O4 1.225(2) . ?
C12 C13 1.384(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
N2 C1 C2 112.56(16) . . ?
C3 C2 C1 135.12(18) . . ?
C7 C2 C1 104.53(16) . . ?
C7 C2 C3 120.34(17) . . ?
C4 C3 C2 117.82(18) . . ?
C3 C4 C5 121.35(18) . . ?
C6 C5 C4 121.66(18) . . ?
C5 C6 C7 116.70(17) . . ?
C6 C7 C2 122.12(17) . . ?
N1 C7 C2 106.14(15) . . ?
N1 C7 C6 131.74(17) . . ?
C1 N2 N1 105.54(15) . . ?
C7 N1 C8 129.66(15) . . ?
N2 N1 C7 111.23(15) . . ?
N2 N1 C8 118.73(15) . . ?
N1 C8 C9 121.82(16) . . ?
N1 C8 C13 120.29(16) . . ?
C13 C8 C9 117.81(16) . . ?
C8 C9 N3 121.75(16) . . ?
C10 C9 C8 122.42(17) . . ?
C10 C9 N3 115.79(17) . . ?
O1 N3 C9 118.07(16) . . ?
O1 N3 O2 124.61(16) . . ?
O2 N3 C9 117.24(17) . . ?
C9 C10 C11 117.49(17) . . ?
C10 C11 N4 118.29(17) . . ?
C12 C11 C10 122.44(17) . . ?
C12 C11 N4 119.26(16) . . ?
O3 N4 C11 118.25(16) . . ?
O3 N4 O4 124.06(17) . . ?
O4 N4 C11 117.69(17) . . ?
C11 C12 C13 118.93(17) . . ?
C12 C13 C8 120.88(17) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2 5 6 0.0443 2.0000 5.0000 6.0000 0.1492 -0.0375 1.0060
-2 -5 -6 0.0443 -2.0000 -5.0000 -6.0000 -0.1492 0.0375 -1.0060
-3 4 -5 0.0415 -3.0000 4.0000 -5.0000 0.5956 -0.7335 -0.3095
3 -4 5 0.0415 3.0000 -4.0000 5.0000 -0.5956 0.7335 0.3095
2 -1 -9 0.0311 2.0000 -1.0000 -9.0000 -0.7513 -0.5744 -0.3480
-2 1 9 0.0311 -2.0000 1.0000 9.0000 0.7513 0.5744 0.3480




data_global

data_4_120K_new2
#TrackingRef 'web_deposit_cif_file_0_SantiagoGarcia-Granda_1366582033.4-120K_806880_new2.cif'

#CCDC-806880

_audit_update_record             
;
2013-04-21 # Formatted by publCIF
;
_audit_creation_date             2013-04-20
_audit_creation_method           
;
Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 N4 O4'
_chemical_formula_sum            'C13 H8 N4 O4'
_chemical_formula_weight         284.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H8 N4 O4'
_chemical_oxdiff_usercomment     'Medida GMN10041 (RT)'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.0730(5)
_cell_length_b                   24.0840(16)
_cell_length_c                   14.3289(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.633(7)
_cell_angle_gamma                90.00
_cell_volume                     2399.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2516
_cell_measurement_temperature    120
_cell_measurement_theta_max      70.5384
_cell_measurement_theta_min      3.6327
_exptl_absorpt_coefficient_mu    1.028
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET)
(compiled Dec 8 2009,17:31:18)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.2515
_exptl_crystal_size_mid          0.0499
_exptl_crystal_size_min          0.0147
_exptl_special_details           ?
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16197
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         70.67
_diffrn_reflns_theta_min         3.64
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 10.2673
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega -116.00 -17.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 -37.0000 -30.0000 99

#__ type_ start__ end____ width___ exp.time_
2 omega -68.00 28.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 37.0000 150.0000 96

#__ type_ start__ end____ width___ exp.time_
3 omega -67.00 32.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 37.0000 60.0000 99

#__ type_ start__ end____ width___ exp.time_
4 omega 46.00 112.00 1.0000 80.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -101.0000 -68.0000 66

#__ type_ start__ end____ width___ exp.time_
5 omega 99.00 150.00 1.0000 80.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -15.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
6 omega 56.00 134.00 1.0000 80.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 179.0000 120.0000 78

#__ type_ start__ end____ width___ exp.time_
7 omega 30.00 83.00 1.0000 80.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -15.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
8 omega 66.00 174.00 1.0000 80.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 77.0000 30.0000 108

#__ type_ start__ end____ width___ exp.time_
9 omega 70.00 144.00 1.0000 80.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 179.0000 150.0000 74

#__ type_ start__ end____ width___ exp.time_
10 omega 108.00 175.00 1.0000 80.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 111.0000 90.0000 67

#__ type_ start__ end____ width___ exp.time_
11 omega 66.00 177.00 1.0000 80.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 77.0000 0.0000 111

#__ type_ start__ end____ width___ exp.time_
12 omega 80.00 147.00 1.0000 80.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 179.0000 -150.0000 67

#__ type_ start__ end____ width___ exp.time_
13 omega 77.00 174.00 1.0000 80.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 45.0000 -120.0000 97
;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0337704000
_diffrn_orient_matrix_UB_12      -0.0585500000
_diffrn_orient_matrix_UB_13      0.0428713000
_diffrn_orient_matrix_UB_21      0.0963192000
_diffrn_orient_matrix_UB_22      -0.0175718000
_diffrn_orient_matrix_UB_23      -0.0836007000
_diffrn_orient_matrix_UB_31      0.1965184000
_diffrn_orient_matrix_UB_32      0.0186709000
_diffrn_orient_matrix_UB_33      0.0563464000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3031
_reflns_number_total             4554
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_iscentric 0
_reflns_odcompleteness_theta     66.49
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET)
(compiled Dec 8 2009,17:31:18)
;
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET)
(compiled Dec 8 2009,17:31:18)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET)
(compiled Dec 8 2009,17:31:18)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         4554
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      0.984
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0294P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1085
_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
C1A C 0.7368(3) 0.30364(10) 0.47816(18) 0.0286(5) Uani 1 1 d . . .
C2A C 0.8049(4) 0.34415(10) 0.54796(18) 0.0317(6) Uani 1 1 d . . .
H2A H 0.8674 0.3338 0.6100 0.038 Uiso 1 1 calc R . .
C3A C 0.7774(4) 0.39887(11) 0.52266(19) 0.0324(5) Uani 1 1 d . . .
H3A H 0.8197 0.4268 0.5686 0.039 Uiso 1 1 calc R . .
C4A C 0.6868(4) 0.41498(11) 0.4292(2) 0.0349(6) Uani 1 1 d . . .
H4A H 0.6727 0.4534 0.4144 0.042 Uiso 1 1 calc R . .
C5A C 0.6202(4) 0.37705(10) 0.36101(18) 0.0313(5) Uani 1 1 d . . .
H5A H 0.5605 0.3883 0.2990 0.038 Uiso 1 1 calc R . .
C6A C 0.6429(3) 0.31990(10) 0.38542(17) 0.0285(5) Uani 1 1 d . . .
C7A C 0.5924(3) 0.27055(10) 0.33746(18) 0.0308(5) Uani 1 1 d . . .
H7A H 0.5278 0.2664 0.2736 0.037 Uiso 1 1 calc R . .
N2A N 0.6546(3) 0.22929(8) 0.40068(14) 0.0276(4) Uani 1 1 d . . .
N1A N 0.7451(3) 0.24789(8) 0.48777(14) 0.0294(5) Uani 1 1 d . . .
C8A C 0.6407(3) 0.17175(10) 0.38309(17) 0.0282(5) Uani 1 1 d . . .
C9A C 0.6348(3) 0.15279(10) 0.29077(18) 0.0309(5) Uani 1 1 d . . .
H9A H 0.6405 0.1788 0.2415 0.037 Uiso 1 1 calc R . .
C10A C 0.6207(3) 0.09648(11) 0.26975(19) 0.0337(6) Uani 1 1 d . . .
H10A H 0.6164 0.0837 0.2067 0.040 Uiso 1 1 calc R . .
C11A C 0.6129(3) 0.05938(10) 0.34249(18) 0.0300(5) Uani 1 1 d . . .
N4A N 0.5981(3) -0.00024(9) 0.32118(16) 0.0361(5) Uani 1 1 d . . .
O4A O 0.5767(3) -0.03236(8) 0.38500(14) 0.0445(5) Uani 1 1 d . . .
O3A O 0.6072(3) -0.01443(8) 0.24025(15) 0.0517(5) Uani 1 1 d . . .
C12A C 0.6225(3) 0.07605(10) 0.43535(18) 0.0303(5) Uani 1 1 d . . .
H12A H 0.6192 0.0498 0.4845 0.036 Uiso 1 1 calc R . .
C13A C 0.6370(3) 0.13254(10) 0.45447(17) 0.0293(5) Uani 1 1 d . . .
N3A N 0.6495(3) 0.14743(8) 0.55580(15) 0.0304(5) Uani 1 1 d . . .
O1A O 0.5181(3) 0.17322(8) 0.57906(13) 0.0377(4) Uani 1 1 d . . .
O2A O 0.7903(3) 0.12925(8) 0.61073(13) 0.0395(5) Uani 1 1 d . . .
C1B C 0.8559(3) 0.87647(9) 0.69022(17) 0.0258(5) Uani 1 1 d . . .
C2B C 0.8534(3) 0.91840(10) 0.75954(17) 0.0302(5) Uani 1 1 d . . .
H2B H 0.8363 0.9093 0.8220 0.036 Uiso 1 1 calc R . .
C3B C 0.8763(3) 0.97206(10) 0.73398(18) 0.0316(6) Uani 1 1 d . . .
H3B H 0.8766 1.0006 0.7798 0.038 Uiso 1 1 calc R . .
C4B C 0.8999(3) 0.98664(10) 0.64072(19) 0.0332(6) Uani 1 1 d . . .
H4B H 0.9127 1.0247 0.6254 0.040 Uiso 1 1 calc R . .
C5B C 0.9045(3) 0.94725(10) 0.57259(18) 0.0305(5) Uani 1 1 d . . .
H5B H 0.9213 0.9573 0.5105 0.037 Uiso 1 1 calc R . .
C6B C 0.8835(3) 0.89080(10) 0.59721(16) 0.0253(5) Uani 1 1 d . . .
C7B C 0.8819(3) 0.84047(10) 0.55021(17) 0.0270(5) Uani 1 1 d . . .
H7B H 0.8983 0.8348 0.4866 0.032 Uiso 1 1 calc R . .
N2B N 0.8524(3) 0.80095(8) 0.61313(13) 0.0253(4) Uani 1 1 d . . .
N1B N 0.8351(3) 0.82131(8) 0.70040(13) 0.0276(4) Uani 1 1 d . . .
C8B C 0.8340(3) 0.74321(9) 0.59512(16) 0.0249(5) Uani 1 1 d . . .
C9B C 0.7584(3) 0.72536(10) 0.50299(17) 0.0272(5) Uani 1 1 d . . .
H9B H 0.7220 0.7519 0.4540 0.033 Uiso 1 1 calc R . .
C10B C 0.7362(3) 0.66967(10) 0.48265(17) 0.0277(5) Uani 1 1 d . . .
H10B H 0.6848 0.6577 0.4199 0.033 Uiso 1 1 calc R . .
C11B C 0.7897(3) 0.63107(10) 0.55471(17) 0.0273(5) Uani 1 1 d . . .
N4B N 0.7698(3) 0.57194(8) 0.53234(15) 0.0314(5) Uani 1 1 d . . .
O4B O 0.6840(3) 0.55857(8) 0.45312(13) 0.0401(5) Uani 1 1 d . . .
O3B O 0.8398(3) 0.53869(7) 0.59382(14) 0.0433(5) Uani 1 1 d . . .
C12B C 0.8611(3) 0.64706(10) 0.64682(17) 0.0282(5) Uani 1 1 d . . .
H12B H 0.8948 0.6203 0.6958 0.034 Uiso 1 1 calc R . .
C13B C 0.8821(3) 0.70315(10) 0.66578(16) 0.0264(5) Uani 1 1 d . . .
N3B N 0.9577(3) 0.71823(8) 0.76557(14) 0.0293(4) Uani 1 1 d . . .
O1B O 1.1113(3) 0.74241(7) 0.78384(13) 0.0363(4) Uani 1 1 d . . .
O2B O 0.8597(3) 0.70327(8) 0.82330(12) 0.0389(4) Uani 1 1 d . . .


_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
C1A C2A 1.416(4) . ?
C1A C6A 1.426(4) . ?
C1A N1A 1.350(3) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.371(4) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.427(4) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.357(4) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.422(4) . ?
C6A C7A 1.386(3) . ?
C7A H7A 0.9500 . ?
C7A N2A 1.362(3) . ?
N2A N1A 1.369(3) . ?
N2A C8A 1.409(3) . ?
C8A C9A 1.393(4) . ?
C8A C13A 1.396(4) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.389(4) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.382(4) . ?
C11A N4A 1.468(3) . ?
C11A C12A 1.379(4) . ?
N4A O4A 1.228(3) . ?
N4A O3A 1.222(3) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.388(4) . ?
C13A N3A 1.482(3) . ?
N3A O1A 1.214(3) . ?
N3A O2A 1.230(3) . ?
C1B C2B 1.419(3) . ?
C1B C6B 1.425(4) . ?
C1B N1B 1.347(3) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.361(4) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.421(4) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.366(4) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.419(3) . ?
C6B C7B 1.386(3) . ?
C7B H7B 0.9500 . ?
C7B N2B 1.353(3) . ?
N2B N1B 1.370(3) . ?
N2B C8B 1.416(3) . ?
C8B C9B 1.397(3) . ?
C8B C13B 1.394(3) . ?
C9B H9B 0.9500 . ?
C9B C10B 1.376(4) . ?
C10B H10B 0.9500 . ?
C10B C11B 1.389(3) . ?
C11B N4B 1.461(3) . ?
C11B C12B 1.378(3) . ?
N4B O4B 1.227(3) . ?
N4B O3B 1.225(3) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.381(3) . ?
C13B N3B 1.477(3) . ?
N3B O1B 1.218(3) . ?
N3B O2B 1.227(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
C2A C1A C6A 120.5(2) . . ?
N1A C1A C2A 127.6(2) . . ?
N1A C1A C6A 111.8(2) . . ?
C1A C2A H2A 121.2 . . ?
C3A C2A C1A 117.5(2) . . ?
C3A C2A H2A 121.2 . . ?
C2A C3A H3A 119.1 . . ?
C2A C3A C4A 121.8(2) . . ?
C4A C3A H3A 119.1 . . ?
C3A C4A H4A 119.0 . . ?
C5A C4A C3A 121.9(2) . . ?
C5A C4A H4A 119.0 . . ?
C4A C5A H5A 121.1 . . ?
C4A C5A C6A 117.8(2) . . ?
C6A C5A H5A 121.1 . . ?
C5A C6A C1A 120.5(2) . . ?
C7A C6A C1A 105.0(2) . . ?
C7A C6A C5A 134.5(2) . . ?
C6A C7A H7A 127.0 . . ?
N2A C7A C6A 105.9(2) . . ?
N2A C7A H7A 127.0 . . ?
C7A N2A N1A 114.01(19) . . ?
C7A N2A C8A 126.6(2) . . ?
N1A N2A C8A 119.39(19) . . ?
C1A N1A N2A 103.20(19) . . ?
C9A C8A N2A 118.8(2) . . ?
C9A C8A C13A 118.2(2) . . ?
C13A C8A N2A 123.0(2) . . ?
C8A C9A H9A 119.5 . . ?
C10A C9A C8A 121.0(2) . . ?
C10A C9A H9A 119.5 . . ?
C9A C10A H10A 120.7 . . ?
C11A C10A C9A 118.6(2) . . ?
C11A C10A H10A 120.7 . . ?
C10A C11A N4A 119.1(2) . . ?
C12A C11A C10A 122.5(2) . . ?
C12A C11A N4A 118.3(2) . . ?
O4A N4A C11A 118.4(2) . . ?
O3A N4A C11A 117.2(2) . . ?
O3A N4A O4A 124.5(2) . . ?
C11A C12A H12A 121.2 . . ?
C11A C12A C13A 117.7(2) . . ?
C13A C12A H12A 121.2 . . ?
C8A C13A N3A 123.3(2) . . ?
C12A C13A C8A 122.0(2) . . ?
C12A C13A N3A 114.8(2) . . ?
O1A N3A C13A 118.83(18) . . ?
O1A N3A O2A 125.2(2) . . ?
O2A N3A C13A 115.8(2) . . ?
C2B C1B C6B 120.3(2) . . ?
N1B C1B C2B 127.6(2) . . ?
N1B C1B C6B 112.1(2) . . ?
C1B C2B H2B 121.0 . . ?
C3B C2B C1B 118.0(2) . . ?
C3B C2B H2B 121.0 . . ?
C2B C3B H3B 119.1 . . ?
C2B C3B C4B 121.9(2) . . ?
C4B C3B H3B 119.1 . . ?
C3B C4B H4B 119.2 . . ?
C5B C4B C3B 121.5(2) . . ?
C5B C4B H4B 119.2 . . ?
C4B C5B H5B 121.0 . . ?
C4B C5B C6B 118.1(2) . . ?
C6B C5B H5B 121.0 . . ?
C5B C6B C1B 120.2(2) . . ?
C7B C6B C1B 104.6(2) . . ?
C7B C6B C5B 135.2(2) . . ?
C6B C7B H7B 126.9 . . ?
N2B C7B C6B 106.3(2) . . ?
N2B C7B H7B 126.9 . . ?
C7B N2B N1B 114.02(19) . . ?
C7B N2B C8B 126.1(2) . . ?
N1B N2B C8B 119.83(19) . . ?
C1B N1B N2B 102.96(19) . . ?
C9B C8B N2B 118.7(2) . . ?
C13B C8B N2B 123.0(2) . . ?
C13B C8B C9B 118.2(2) . . ?
C8B C9B H9B 119.7 . . ?
C10B C9B C8B 120.6(2) . . ?
C10B C9B H9B 119.7 . . ?
C9B C10B H10B 120.3 . . ?
C9B C10B C11B 119.4(2) . . ?
C11B C10B H10B 120.3 . . ?
C10B C11B N4B 119.2(2) . . ?
C12B C11B C10B 121.8(2) . . ?
C12B C11B N4B 119.1(2) . . ?
O4B N4B C11B 118.0(2) . . ?
O3B N4B C11B 118.01(19) . . ?
O3B N4B O4B 124.0(2) . . ?
C11B C12B H12B 121.0 . . ?
C11B C12B C13B 118.0(2) . . ?
C13B C12B H12B 121.0 . . ?
C8B C13B N3B 122.0(2) . . ?
C12B C13B C8B 122.1(2) . . ?
C12B C13B N3B 116.0(2) . . ?
O1B N3B C13B 118.4(2) . . ?
O1B N3B O2B 126.0(2) . . ?
O2B N3B C13B 115.6(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
C1A C2A C3A C4A -1.1(4) . . . . ?
C1A C6A C7A N2A 0.3(3) . . . . ?
C2A C1A C6A C5A 1.5(4) . . . . ?
C2A C1A C6A C7A -178.6(2) . . . . ?
C2A C1A N1A N2A 178.2(2) . . . . ?
C2A C3A C4A C5A 1.2(4) . . . . ?
C3A C4A C5A C6A 0.2(4) . . . . ?
C4A C5A C6A C1A -1.4(4) . . . . ?
C4A C5A C6A C7A 178.7(3) . . . . ?
C5A C6A C7A N2A -179.9(3) . . . . ?
C6A C1A C2A C3A -0.2(4) . . . . ?
C6A C1A N1A N2A -0.4(3) . . . . ?
C6A C7A N2A N1A -0.6(3) . . . . ?
C6A C7A N2A C8A -177.9(2) . . . . ?
C7A N2A N1A C1A 0.6(3) . . . . ?
C7A N2A C8A C9A 26.8(4) . . . . ?
C7A N2A C8A C13A -154.8(2) . . . . ?
N2A C8A C9A C10A -179.9(2) . . . . ?
N2A C8A C13A C12A 179.8(2) . . . . ?
N2A C8A C13A N3A -0.7(4) . . . . ?
N1A C1A C2A C3A -178.7(3) . . . . ?
N1A C1A C6A C5A -179.8(2) . . . . ?
N1A C1A C6A C7A 0.1(3) . . . . ?
N1A N2A C8A C9A -150.4(2) . . . . ?
N1A N2A C8A C13A 28.0(3) . . . . ?
C8A N2A N1A C1A 178.1(2) . . . . ?
C8A C9A C10A C11A -0.1(4) . . . . ?
C8A C13A N3A O1A 66.6(3) . . . . ?
C8A C13A N3A O2A -117.6(2) . . . . ?
C9A C8A C13A C12A -1.8(3) . . . . ?
C9A C8A C13A N3A 177.8(2) . . . . ?
C9A C10A C11A N4A -180.0(2) . . . . ?
C9A C10A C11A C12A -1.3(4) . . . . ?
C10A C11A N4A O4A -174.5(2) . . . . ?
C10A C11A N4A O3A 5.1(3) . . . . ?
C10A C11A C12A C13A 1.1(4) . . . . ?
C11A C12A C13A C8A 0.5(4) . . . . ?
C11A C12A C13A N3A -179.1(2) . . . . ?
N4A C11A C12A C13A 179.8(2) . . . . ?
C12A C11A N4A O4A 6.7(3) . . . . ?
C12A C11A N4A O3A -173.6(2) . . . . ?
C12A C13A N3A O1A -113.8(2) . . . . ?
C12A C13A N3A O2A 62.0(3) . . . . ?
C13A C8A C9A C10A 1.6(3) . . . . ?
C1B C2B C3B C4B 0.7(4) . . . . ?
C1B C6B C7B N2B 0.8(2) . . . . ?
C2B C1B C6B C5B -1.4(3) . . . . ?
C2B C1B C6B C7B 178.8(2) . . . . ?
C2B C1B N1B N2B -179.0(2) . . . . ?
C2B C3B C4B C5B -1.3(4) . . . . ?
C3B C4B C5B C6B 0.5(4) . . . . ?
C4B C5B C6B C1B 0.9(3) . . . . ?
C4B C5B C6B C7B -179.4(3) . . . . ?
C5B C6B C7B N2B -178.9(2) . . . . ?
C6B C1B C2B C3B 0.6(3) . . . . ?
C6B C1B N1B N2B 0.7(2) . . . . ?
C6B C7B N2B N1B -0.4(3) . . . . ?
C6B C7B N2B C8B 177.9(2) . . . . ?
C7B N2B N1B C1B -0.2(2) . . . . ?
C7B N2B C8B C9B -29.4(3) . . . . ?
C7B N2B C8B C13B 152.7(2) . . . . ?
N2B C8B C9B C10B -179.3(2) . . . . ?
N2B C8B C13B C12B 179.3(2) . . . . ?
N2B C8B C13B N3B -0.4(4) . . . . ?
N1B C1B C2B C3B -179.7(2) . . . . ?
N1B C1B C6B C5B 178.8(2) . . . . ?
N1B C1B C6B C7B -1.0(3) . . . . ?
N1B N2B C8B C9B 148.8(2) . . . . ?
N1B N2B C8B C13B -29.1(3) . . . . ?
C8B N2B N1B C1B -178.60(19) . . . . ?
C8B C9B C10B C11B 0.0(4) . . . . ?
C8B C13B N3B O1B -63.1(3) . . . . ?
C8B C13B N3B O2B 119.0(3) . . . . ?
C9B C8B C13B C12B 1.4(4) . . . . ?
C9B C8B C13B N3B -178.3(2) . . . . ?
C9B C10B C11B N4B -178.7(2) . . . . ?
C9B C10B C11B C12B 1.3(4) . . . . ?
C10B C11B N4B O4B -9.0(3) . . . . ?
C10B C11B N4B O3B 171.0(2) . . . . ?
C10B C11B C12B C13B -1.2(4) . . . . ?
C11B C12B C13B C8B -0.1(4) . . . . ?
C11B C12B C13B N3B 179.5(2) . . . . ?
N4B C11B C12B C13B 178.7(2) . . . . ?
C12B C11B N4B O4B 171.0(2) . . . . ?
C12B C11B N4B O3B -9.0(3) . . . . ?
C12B C13B N3B O1B 117.2(3) . . . . ?
C12B C13B N3B O2B -60.7(3) . . . . ?
C13B C8B C9B C10B -1.3(4) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 9 7 0.0105 -0.0046 9.0049 6.9947 -0.2213 -0.7424 0.5625
0 -9 -7 0.0105 0.0046 -9.0049 -6.9947 0.2213 0.7424 -0.5625
5 -1 -1 0.1223 5.0015 -0.9700 -0.9914 0.1854 0.5853 0.9080
-5 1 1 0.1223 -5.0015 0.9700 0.9914 -0.1854 -0.5853 -0.9080
0 -15 -2 0.0073 0.0045 -14.9882 -1.9914 0.7881 0.4339 -0.3948
0 15 2 0.0073 -0.0045 14.9882 1.9914 -0.7881 -0.4339 0.3948




data_global

data_4_293K_new
#TrackingRef 'web_deposit_cif_file_0_SantiagoGarcia-Granda_1365518504.4-293K_806881_new.cif'

#CCDC-806881
_audit_update_record             
;
2013-04-08 # Formatted by publCIF
;
_audit_creation_date             2013-04-07
_audit_creation_method           
;
Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 N4 O4'
_chemical_formula_sum            'C13 H8 N4 O4'
_chemical_formula_weight         284.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H8 N4 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.2107(6)
_cell_length_b                   24.0635(17)
_cell_length_c                   14.4077(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.334(17)
_cell_angle_gamma                90.00
_cell_volume                     2459.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1341
_cell_measurement_temperature    298
_cell_measurement_theta_max      70.5781
_cell_measurement_theta_min      3.6161
_exptl_absorpt_coefficient_mu    1.003
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET)
(compiled Dec 8 2009,17:31:18)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.2843
_exptl_crystal_size_mid          0.021
_exptl_crystal_size_min          0.0135
_exptl_special_details           ?
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8843
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         70.71
_diffrn_reflns_theta_min         3.62
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 10.2673
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega -68.00 29.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 37.0000 -90.0000 97

#__ type_ start__ end____ width___ exp.time_
2 omega 48.00 99.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- 41.6979 -125.0000 30.0000 51

#__ type_ start__ end____ width___ exp.time_
3 omega -24.00 11.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- 41.6979 -37.0000 30.0000 35

#__ type_ start__ end____ width___ exp.time_
4 omega 72.00 173.00 1.0000 90.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 45.0000 30.0000 101

#__ type_ start__ end____ width___ exp.time_
5 omega 99.00 125.00 1.0000 90.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -45.0000 150.0000 26

#__ type_ start__ end____ width___ exp.time_
6 omega 140.00 169.00 1.0000 90.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 111.0000 150.0000 29

#__ type_ start__ end____ width___ exp.time_
7 omega 91.00 117.00 1.0000 90.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -45.0000 60.0000 26

#__ type_ start__ end____ width___ exp.time_
8 omega 90.00 128.00 1.0000 90.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -45.0000 90.0000 38

#__ type_ start__ end____ width___ exp.time_
9 omega 94.00 128.00 1.0000 90.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -45.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
10 omega 17.00 107.00 1.0000 90.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -97.0000 -39.0000 90

#__ type_ start__ end____ width___ exp.time_
11 omega 96.00 128.00 1.0000 90.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -45.0000 -60.0000 32

#__ type_ start__ end____ width___ exp.time_
12 omega 95.00 120.00 1.0000 90.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -45.0000 30.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0860319000
_diffrn_orient_matrix_UB_12      -0.0583816000
_diffrn_orient_matrix_UB_13      0.0031763000
_diffrn_orient_matrix_UB_21      -0.0680906000
_diffrn_orient_matrix_UB_22      0.0153492000
_diffrn_orient_matrix_UB_23      0.0921980000
_diffrn_orient_matrix_UB_31      -0.1872563000
_diffrn_orient_matrix_UB_32      0.0213073000
_diffrn_orient_matrix_UB_33      -0.0576293000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2303
_reflns_number_total             4556
_reflns_odcompleteness_completeness 98.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET)
(compiled Dec 8 2009,17:31:18)
;
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET)
(compiled Dec 8 2009,17:31:18)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET)
(compiled Dec 8 2009,17:31:18)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         4556
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1325
_refine_ls_R_factor_gt           0.0599
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0385P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1709
_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
C1A C 0.7397(6) 0.30330(16) 0.4763(3) 0.0447(9) Uani 1 1 d . . .
C2A C 0.8063(6) 0.34369(18) 0.5449(3) 0.0531(10) Uani 1 1 d . . .
H2A H 0.8663 0.3335 0.6052 0.064 Uiso 1 1 calc R . .
C3A C 0.7800(7) 0.39801(19) 0.5203(3) 0.0596(11) Uani 1 1 d . . .
H3A H 0.8233 0.4253 0.5646 0.072 Uiso 1 1 calc R . .
C4A C 0.6874(7) 0.4142(2) 0.4281(4) 0.0629(12) Uani 1 1 d . . .
H4A H 0.6712 0.4518 0.4144 0.076 Uiso 1 1 calc R . .
C5A C 0.6227(7) 0.37671(19) 0.3603(3) 0.0590(11) Uani 1 1 d . . .
H5A H 0.5655 0.3879 0.3002 0.071 Uiso 1 1 calc R . .
C6A C 0.6454(6) 0.31892(17) 0.3842(3) 0.0466(9) Uani 1 1 d . . .
C7A C 0.5956(6) 0.27024(18) 0.3381(3) 0.0494(10) Uani 1 1 d . . .
H7A H 0.5314 0.2662 0.2764 0.059 Uiso 1 1 calc R . .
N2A N 0.6579(4) 0.22883(14) 0.3996(2) 0.0449(8) Uani 1 1 d . . .
N1A N 0.7473(5) 0.24747(14) 0.4857(2) 0.0481(8) Uani 1 1 d . . .
C8A C 0.6431(5) 0.17119(17) 0.3827(3) 0.0447(9) Uani 1 1 d . . .
C9A C 0.6374(6) 0.15187(19) 0.2906(3) 0.0526(10) Uani 1 1 d . . .
H9A H 0.6433 0.1770 0.2422 0.063 Uiso 1 1 calc R . .
C10A C 0.6230(6) 0.09572(19) 0.2712(3) 0.0565(11) Uani 1 1 d . . .
H10A H 0.6185 0.0830 0.2099 0.068 Uiso 1 1 calc R . .
C11A C 0.6153(6) 0.05894(18) 0.3429(3) 0.0526(10) Uani 1 1 d . . .
N4A N 0.6003(6) -0.00041(17) 0.3224(3) 0.0649(11) Uani 1 1 d . . .
O4A O 0.5811(6) -0.03244(15) 0.3857(3) 0.0869(11) Uani 1 1 d . . .
O3A O 0.6056(7) -0.01502(17) 0.2424(3) 0.1049(15) Uani 1 1 d . . .
C12A C 0.6231(5) 0.07642(18) 0.4345(3) 0.0494(10) Uani 1 1 d . . .
H12A H 0.6178 0.0509 0.4824 0.059 Uiso 1 1 calc R . .
C13A C 0.6387(5) 0.13185(17) 0.4537(3) 0.0451(9) Uani 1 1 d . . .
N3A N 0.6476(5) 0.14745(14) 0.5539(2) 0.0508(8) Uani 1 1 d . . .
O1A O 0.5186(5) 0.17411(15) 0.5756(2) 0.0666(8) Uani 1 1 d . . .
O2A O 0.7828(5) 0.12937(15) 0.6087(2) 0.0726(10) Uani 1 1 d . . .
C1B C 0.8512(5) 0.87630(16) 0.6905(3) 0.0434(9) Uani 1 1 d . . .
C2B C 0.8486(6) 0.91826(18) 0.7582(3) 0.0533(11) Uani 1 1 d . . .
H2B H 0.8306 0.9095 0.8189 0.064 Uiso 1 1 calc R . .
C3B C 0.8728(6) 0.97173(19) 0.7335(3) 0.0575(11) Uani 1 1 d . . .
H3B H 0.8712 0.9996 0.7780 0.069 Uiso 1 1 calc R . .
C4B C 0.9006(6) 0.98629(19) 0.6418(3) 0.0587(11) Uani 1 1 d . . .
H4B H 0.9152 1.0235 0.6271 0.070 Uiso 1 1 calc R . .
C5B C 0.9063(6) 0.94675(18) 0.5745(3) 0.0530(10) Uani 1 1 d . . .
H5B H 0.9254 0.9566 0.5145 0.064 Uiso 1 1 calc R . .
C6B C 0.8827(5) 0.89056(18) 0.5981(3) 0.0442(9) Uani 1 1 d . . .
C7B C 0.8810(5) 0.84017(16) 0.5525(3) 0.0432(9) Uani 1 1 d . . .
H7B H 0.8985 0.8345 0.4907 0.052 Uiso 1 1 calc R . .
N2B N 0.8494(4) 0.80051(13) 0.6139(2) 0.0411(7) Uani 1 1 d . . .
N1B N 0.8296(5) 0.82138(14) 0.7003(2) 0.0463(8) Uani 1 1 d . . .
C8B C 0.8312(5) 0.74293(16) 0.5965(3) 0.0412(8) Uani 1 1 d . . .
C9B C 0.7581(6) 0.72478(17) 0.5050(3) 0.0457(9) Uani 1 1 d . . .
H9B H 0.7228 0.7507 0.4572 0.055 Uiso 1 1 calc R . .
C10B C 0.7381(6) 0.66951(17) 0.4851(3) 0.0485(10) Uani 1 1 d . . .
H10B H 0.6908 0.6577 0.4240 0.058 Uiso 1 1 calc R . .
C11B C 0.7879(6) 0.63154(17) 0.5557(3) 0.0488(10) Uani 1 1 d . . .
N4B N 0.7709(6) 0.57175(16) 0.5349(3) 0.0602(10) Uani 1 1 d . . .
O4B O 0.6871(6) 0.55826(14) 0.4562(2) 0.0802(11) Uani 1 1 d . . .
O3B O 0.8374(6) 0.53876(14) 0.5953(3) 0.0844(11) Uani 1 1 d . . .
C12B C 0.8567(6) 0.64715(17) 0.6477(3) 0.0480(9) Uani 1 1 d . . .
H12B H 0.8876 0.6208 0.6952 0.058 Uiso 1 1 calc R . .
C13B C 0.8781(5) 0.70298(17) 0.6668(2) 0.0428(9) Uani 1 1 d . . .
N3B N 0.9532(5) 0.71817(15) 0.7650(2) 0.0494(8) Uani 1 1 d . . .
O1B O 1.1026(4) 0.74244(15) 0.7823(2) 0.0645(8) Uani 1 1 d . . .
O2B O 0.8596(5) 0.70376(17) 0.8235(2) 0.0755(10) Uani 1 1 d . . .


_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
C1A C2A 1.408(6) . ?
C1A C6A 1.428(5) . ?
C1A N1A 1.351(5) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.359(6) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.430(7) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.350(7) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.435(6) . ?
C6A C7A 1.363(6) . ?
C7A H7A 0.9300 . ?
C7A N2A 1.356(5) . ?
N2A N1A 1.367(4) . ?
N2A C8A 1.409(5) . ?
C8A C9A 1.400(6) . ?
C8A C13A 1.398(6) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.380(6) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.370(7) . ?
C11A N4A 1.459(6) . ?
C11A C12A 1.377(6) . ?
N4A O4A 1.220(5) . ?
N4A O3A 1.212(5) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.363(6) . ?
C13A N3A 1.482(5) . ?
N3A O1A 1.216(4) . ?
N3A O2A 1.219(4) . ?
C1B C2B 1.407(6) . ?
C1B C6B 1.432(6) . ?
C1B N1B 1.341(5) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.355(7) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.415(7) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.364(6) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.412(6) . ?
C6B C7B 1.378(6) . ?
C7B H7B 0.9300 . ?
C7B N2B 1.349(5) . ?
N2B N1B 1.373(4) . ?
N2B C8B 1.410(5) . ?
C8B C9B 1.399(5) . ?
C8B C13B 1.393(5) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.363(6) . ?
C10B H10B 0.9300 . ?
C10B C11B 1.367(6) . ?
C11B N4B 1.470(6) . ?
C11B C12B 1.381(6) . ?
N4B O4B 1.229(5) . ?
N4B O3B 1.212(5) . ?
C12B H12B 0.9300 . ?
C12B C13B 1.374(6) . ?
C13B N3B 1.469(5) . ?
N3B O1B 1.211(4) . ?
N3B O2B 1.221(5) . ?

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 C1A C6A 121.1(4) . . ?
N1A C1A C2A 127.8(4) . . ?
N1A C1A C6A 111.0(4) . . ?
C1A C2A H2A 121.1 . . ?
C3A C2A C1A 117.8(4) . . ?
C3A C2A H2A 121.1 . . ?
C2A C3A H3A 119.2 . . ?
C2A C3A C4A 121.6(4) . . ?
C4A C3A H3A 119.2 . . ?
C3A C4A H4A 118.9 . . ?
C5A C4A C3A 122.3(4) . . ?
C5A C4A H4A 118.9 . . ?
C4A C5A H5A 121.2 . . ?
C4A C5A C6A 117.6(4) . . ?
C6A C5A H5A 121.2 . . ?
C1A C6A C5A 119.5(4) . . ?
C7A C6A C1A 105.5(4) . . ?
C7A C6A C5A 135.0(4) . . ?
C6A C7A H7A 126.7 . . ?
N2A C7A C6A 106.6(3) . . ?
N2A C7A H7A 126.7 . . ?
C7A N2A N1A 113.5(3) . . ?
C7A N2A C8A 127.2(3) . . ?
N1A N2A C8A 119.2(3) . . ?
C1A N1A N2A 103.4(3) . . ?
C9A C8A N2A 118.6(4) . . ?
C13A C8A N2A 123.4(4) . . ?
C13A C8A C9A 117.9(4) . . ?
C8A C9A H9A 119.8 . . ?
C10A C9A C8A 120.4(4) . . ?
C10A C9A H9A 119.8 . . ?
C9A C10A H10A 120.3 . . ?
C11A C10A C9A 119.5(4) . . ?
C11A C10A H10A 120.3 . . ?
C10A C11A N4A 119.4(4) . . ?
C10A C11A C12A 121.7(4) . . ?
C12A C11A N4A 118.8(4) . . ?
O4A N4A C11A 118.8(4) . . ?
O3A N4A C11A 117.6(5) . . ?
O3A N4A O4A 123.7(4) . . ?
C11A C12A H12A 120.6 . . ?
C13A C12A C11A 118.7(4) . . ?
C13A C12A H12A 120.6 . . ?
C8A C13A N3A 122.6(4) . . ?
C12A C13A C8A 121.8(4) . . ?
C12A C13A N3A 115.7(4) . . ?
O1A N3A C13A 118.9(3) . . ?
O1A N3A O2A 125.5(4) . . ?
O2A N3A C13A 115.5(4) . . ?
C2B C1B C6B 119.8(4) . . ?
N1B C1B C2B 128.1(4) . . ?
N1B C1B C6B 112.0(3) . . ?
C1B C2B H2B 120.6 . . ?
C3B C2B C1B 118.7(4) . . ?
C3B C2B H2B 120.6 . . ?
C2B C3B H3B 119.1 . . ?
C2B C3B C4B 121.8(4) . . ?
C4B C3B H3B 119.1 . . ?
C3B C4B H4B 119.4 . . ?
C5B C4B C3B 121.2(4) . . ?
C5B C4B H4B 119.4 . . ?
C4B C5B H5B 120.8 . . ?
C4B C5B C6B 118.4(4) . . ?
C6B C5B H5B 120.8 . . ?
C5B C6B C1B 120.0(4) . . ?
C7B C6B C1B 104.1(3) . . ?
C7B C6B C5B 136.0(4) . . ?
C6B C7B H7B 126.4 . . ?
N2B C7B C6B 107.3(3) . . ?
N2B C7B H7B 126.4 . . ?
C7B N2B N1B 113.2(3) . . ?
C7B N2B C8B 126.8(3) . . ?
N1B N2B C8B 120.0(3) . . ?
C1B N1B N2B 103.4(3) . . ?
C9B C8B N2B 118.8(3) . . ?
C13B C8B N2B 123.1(3) . . ?
C13B C8B C9B 118.1(4) . . ?
C8B C9B H9B 119.7 . . ?
C10B C9B C8B 120.7(4) . . ?
C10B C9B H9B 119.7 . . ?
C9B C10B H10B 120.2 . . ?
C9B C10B C11B 119.5(4) . . ?
C11B C10B H10B 120.2 . . ?
C10B C11B N4B 120.1(4) . . ?
C10B C11B C12B 122.2(4) . . ?
C12B C11B N4B 117.7(4) . . ?
O4B N4B C11B 117.1(4) . . ?
O3B N4B C11B 119.1(4) . . ?
O3B N4B O4B 123.8(4) . . ?
C11B C12B H12B 121.1 . . ?
C13B C12B C11B 117.7(4) . . ?
C13B C12B H12B 121.1 . . ?
C8B C13B N3B 121.9(4) . . ?
C12B C13B C8B 121.7(3) . . ?
C12B C13B N3B 116.4(3) . . ?
O1B N3B C13B 118.6(3) . . ?
O1B N3B O2B 125.2(3) . . ?
O2B N3B C13B 116.2(4) . . ?

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
C1A C2A C3A C4A 0.2(7) . . . . ?
C1A C6A C7A N2A -0.2(4) . . . . ?
C2A C1A C6A C5A 1.8(6) . . . . ?
C2A C1A C6A C7A -178.1(4) . . . . ?
C2A C1A N1A N2A 178.0(4) . . . . ?
C2A C3A C4A C5A -0.6(7) . . . . ?
C3A C4A C5A C6A 1.6(7) . . . . ?
C4A C5A C6A C1A -2.1(6) . . . . ?
C4A C5A C6A C7A 177.7(5) . . . . ?
C5A C6A C7A N2A -180.0(5) . . . . ?
C6A C1A C2A C3A -0.8(6) . . . . ?
C6A C1A N1A N2A 0.0(4) . . . . ?
C6A C7A N2A N1A 0.2(5) . . . . ?
C6A C7A N2A C8A -178.3(4) . . . . ?
C7A N2A N1A C1A -0.1(4) . . . . ?
C7A N2A C8A C9A 28.3(6) . . . . ?
C7A N2A C8A C13A -153.5(4) . . . . ?
N2A C8A C9A C10A 180.0(4) . . . . ?
N2A C8A C13A C12A 179.6(4) . . . . ?
N2A C8A C13A N3A 0.6(6) . . . . ?
N1A C1A C2A C3A -178.6(4) . . . . ?
N1A C1A C6A C5A 179.9(4) . . . . ?
N1A C1A C6A C7A 0.1(5) . . . . ?
N1A N2A C8A C9A -150.1(4) . . . . ?
N1A N2A C8A C13A 28.1(6) . . . . ?
C8A N2A N1A C1A 178.5(4) . . . . ?
C8A C9A C10A C11A -0.3(7) . . . . ?
C8A C13A N3A O1A 65.1(5) . . . . ?
C8A C13A N3A O2A -118.5(4) . . . . ?
C9A C8A C13A C12A -2.2(6) . . . . ?
C9A C8A C13A N3A 178.9(4) . . . . ?
C9A C10A C11A N4A -179.9(4) . . . . ?
C9A C10A C11A C12A -0.5(7) . . . . ?
C10A C11A N4A O4A -175.3(4) . . . . ?
C10A C11A N4A O3A 4.0(7) . . . . ?
C10A C11A C12A C13A 0.1(7) . . . . ?
C11A C12A C13A C8A 1.3(6) . . . . ?
C11A C12A C13A N3A -179.6(4) . . . . ?
N4A C11A C12A C13A 179.4(4) . . . . ?
C12A C11A N4A O4A 5.3(7) . . . . ?
C12A C11A N4A O3A -175.4(4) . . . . ?
C12A C13A N3A O1A -113.9(4) . . . . ?
C12A C13A N3A O2A 62.4(5) . . . . ?
C13A C8A C9A C10A 1.6(6) . . . . ?
C1B C2B C3B C4B 0.0(7) . . . . ?
C1B C6B C7B N2B 0.5(4) . . . . ?
C2B C1B C6B C5B -1.6(6) . . . . ?
C2B C1B C6B C7B 178.5(4) . . . . ?
C2B C1B N1B N2B -178.5(4) . . . . ?
C2B C3B C4B C5B -0.8(7) . . . . ?
C3B C4B C5B C6B 0.4(7) . . . . ?
C4B C5B C6B C1B 0.8(6) . . . . ?
C4B C5B C6B C7B -179.3(5) . . . . ?
C5B C6B C7B N2B -179.5(5) . . . . ?
C6B C1B C2B C3B 1.2(6) . . . . ?
C6B C1B N1B N2B 0.6(4) . . . . ?
C6B C7B N2B N1B -0.2(4) . . . . ?
C6B C7B N2B C8B 178.1(4) . . . . ?
C7B N2B N1B C1B -0.3(4) . . . . ?
C7B N2B C8B C9B -30.0(6) . . . . ?
C7B N2B C8B C13B 151.7(4) . . . . ?
N2B C8B C9B C10B -180.0(4) . . . . ?
N2B C8B C13B C12B 179.3(4) . . . . ?
N2B C8B C13B N3B -0.9(6) . . . . ?
N1B C1B C2B C3B -179.8(4) . . . . ?
N1B C1B C6B C5B 179.3(4) . . . . ?
N1B C1B C6B C7B -0.7(5) . . . . ?
N1B N2B C8B C9B 148.1(3) . . . . ?
N1B N2B C8B C13B -30.1(6) . . . . ?
C8B N2B N1B C1B -178.6(3) . . . . ?
C8B C9B C10B C11B 0.8(6) . . . . ?
C8B C13B N3B O1B -62.4(5) . . . . ?
C8B C13B N3B O2B 119.3(4) . . . . ?
C9B C8B C13B C12B 1.0(6) . . . . ?
C9B C8B C13B N3B -179.1(3) . . . . ?
C9B C10B C11B N4B -178.7(4) . . . . ?
C9B C10B C11B C12B 0.7(6) . . . . ?
C10B C11B N4B O4B -9.9(6) . . . . ?
C10B C11B N4B O3B 170.8(4) . . . . ?
C10B C11B C12B C13B -1.3(6) . . . . ?
C11B C12B C13B C8B 0.4(6) . . . . ?
C11B C12B C13B N3B -179.5(4) . . . . ?
N4B C11B C12B C13B 178.1(4) . . . . ?
C12B C11B N4B O4B 170.7(4) . . . . ?
C12B C11B N4B O3B -8.6(6) . . . . ?
C12B C13B N3B O1B 117.5(4) . . . . ?
C12B C13B N3B O2B -60.8(5) . . . . ?
C13B C8B C9B C10B -1.6(6) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 3 -9 0.0105 -0.0029 2.9826 -8.9859 -0.2055 -0.7847 0.5807
0 -3 9 0.0105 0.0029 -2.9826 8.9859 0.2055 0.7847 -0.5807
0 -16 -1 0.0068 0.0036 -15.9774 -1.0010 0.9292 -0.3389 -0.2799
0 16 1 0.0068 -0.0036 15.9774 1.0010 -0.9292 0.3389 0.2799
-4 1 -4 0.1105 -3.9930 0.9884 -3.9968 0.2731 -0.0811 1.0022
4 -1 4 0.1105 3.9930 -0.9884 3.9968 -0.2731 0.0811 -1.0022




data_global

data_5_293K_new
#TrackingRef 'web_deposit_cif_file_0_SantiagoGarcia-Granda_1365518780.5-293K_923952_new.cif'

#CCDC-923952

_audit_update_record             
;
2013-04-08 # Formatted by publCIF
;
_audit_creation_date             2013-03-26
_audit_creation_method           
;
Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 N4 O4'
_chemical_formula_sum            'C13 H8 N4 O4'
_chemical_formula_weight         284.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H8 N4 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   13.0325(6)
_cell_length_b                   15.3958(15)
_cell_length_c                   6.1563(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.558(5)
_cell_angle_gamma                90.00
_cell_volume                     1218.09(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2950
_cell_measurement_temperature    293.0(2)
_cell_measurement_theta_max      70.6813
_cell_measurement_theta_min      3.4362
_exptl_absorpt_coefficient_mu    1.012
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.03
_exptl_special_details           ?
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            13222
_diffrn_reflns_theta_full        70.81
_diffrn_reflns_theta_max         70.81
_diffrn_reflns_theta_min         3.44
_diffrn_ambient_temperature      293.0(2)
_diffrn_detector_area_resol_mean 10.2673
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega -40.00 28.00 1.0000 13.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 37.0000 -150.0000 68

#__ type_ start__ end____ width___ exp.time_
2 omega -80.00 37.00 1.0000 13.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 19.0000 -30.0000 117

#__ type_ start__ end____ width___ exp.time_
3 omega -49.00 29.00 1.0000 13.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 37.0000 30.0000 78

#__ type_ start__ end____ width___ exp.time_
4 omega 22.00 99.00 1.0000 13.0000
omega____ theta____ kappa____ phi______ frames
- 41.6979 -125.0000 150.0000 77

#__ type_ start__ end____ width___ exp.time_
5 omega 32.00 85.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -30.0000 -90.0000 53

#__ type_ start__ end____ width___ exp.time_
6 omega 40.00 174.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 15.0000 -90.0000 134

#__ type_ start__ end____ width___ exp.time_
7 omega 35.00 68.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -30.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
8 omega 49.00 75.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -77.0000 -90.0000 26

#__ type_ start__ end____ width___ exp.time_
9 omega 36.00 109.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -94.0000 -150.0000 73

#__ type_ start__ end____ width___ exp.time_
10 omega 38.00 104.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -61.0000 0.0000 66

#__ type_ start__ end____ width___ exp.time_
11 omega 123.00 175.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 111.0000 -90.0000 52

#__ type_ start__ end____ width___ exp.time_
12 omega 70.00 154.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 61.0000 -60.0000 84

#__ type_ start__ end____ width___ exp.time_
13 omega 60.00 103.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 179.0000 -90.0000 43

#__ type_ start__ end____ width___ exp.time_
14 omega 30.00 87.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -30.0000 30.0000 57

#__ type_ start__ end____ width___ exp.time_
15 omega 23.00 100.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -94.0000 -30.0000 77

#__ type_ start__ end____ width___ exp.time_
16 omega 23.00 75.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -30.0000 -30.0000 52

#__ type_ start__ end____ width___ exp.time_
17 omega 124.00 150.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 179.0000 -90.0000 26

#__ type_ start__ end____ width___ exp.time_
18 omega 50.00 76.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -94.0000 0.0000 26

#__ type_ start__ end____ width___ exp.time_
19 omega 83.00 109.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -94.0000 0.0000 26

#__ type_ start__ end____ width___ exp.time_
20 omega 114.00 174.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 133.0000 42.0000 60

#__ type_ start__ end____ width___ exp.time_
21 omega 148.00 173.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 111.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
22 omega 83.00 113.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 -111.0000 120.0000 30

#__ type_ start__ end____ width___ exp.time_
23 omega -120.00 -8.00 1.0000 13.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 -77.0000 -90.0000 112

#__ type_ start__ end____ width___ exp.time_
24 omega -116.00 -12.00 1.0000 13.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 -57.0000 150.0000 104

#__ type_ start__ end____ width___ exp.time_
25 omega -120.00 -8.00 1.0000 13.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 -77.0000 -30.0000 112

#__ type_ start__ end____ width___ exp.time_
26 omega -116.00 -12.00 1.0000 13.0000
omega____ theta____ kappa____ phi______ frames
- -41.6979 -57.0000 30.0000 104

#__ type_ start__ end____ width___ exp.time_
27 omega 69.00 178.00 1.0000 50.0000
omega____ theta____ kappa____ phi______ frames
- 100.0000 30.0000 90.0000 109
;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0005654000
_diffrn_orient_matrix_UB_12      -0.0989962000
_diffrn_orient_matrix_UB_13      0.0368150000
_diffrn_orient_matrix_UB_21      0.0392575000
_diffrn_orient_matrix_UB_22      0.0139924000
_diffrn_orient_matrix_UB_23      0.2474964000
_diffrn_orient_matrix_UB_31      -0.1133274000
_diffrn_orient_matrix_UB_32      0.0043901000
_diffrn_orient_matrix_UB_33      0.0413123000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1644
_reflns_number_total             2317
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0539P)²+0.1111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1171
_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.72042(12) -0.00010(11) 0.5768(3) 0.0674(5) Uani 1 1 d . . .
C1 C 0.80138(17) 0.03316(16) 0.6565(4) 0.0586(6) Uani 1 1 d . . .
H1 H 0.8248 0.0233 0.8055 0.070 Uiso 1 1 calc R . .
C2 C 0.86680(15) 0.08819(14) 0.5390(3) 0.0504(5) Uani 1 1 d . . .
C3 C 0.97245(16) 0.09499(16) 0.6239(4) 0.0612(6) Uani 1 1 d . . .
H3 H 0.9976 0.0721 0.7623 0.073 Uiso 1 1 calc R . .
C4 C 1.04050(17) 0.13507(18) 0.5061(5) 0.0700(7) Uani 1 1 d . . .
H4 H 1.1110 0.1380 0.5642 0.084 Uiso 1 1 calc R . .
C5 C 1.00438(18) 0.17040(18) 0.3041(5) 0.0723(7) Uani 1 1 d . . .
H5 H 1.0507 0.1960 0.2237 0.087 Uiso 1 1 calc R . .
C6 C 0.89893(17) 0.16831(17) 0.2182(4) 0.0639(6) Uani 1 1 d . . .
H6 H 0.8741 0.1940 0.0830 0.077 Uiso 1 1 calc R . .
C7 C 0.83168(14) 0.12766(14) 0.3360(3) 0.0483(5) Uani 1 1 d . . .
N1 N 0.72418(11) 0.12746(12) 0.2442(2) 0.0479(4) Uani 1 1 d . . .
N2 N 0.65005(12) 0.15943(11) 0.3542(2) 0.0463(4) Uani 1 1 d . . .
O2 O 0.66948(11) 0.19049(11) 0.5463(2) 0.0583(4) Uani 1 1 d . . .
C8 C 0.55874(14) 0.14828(14) 0.2139(3) 0.0454(5) Uani 1 1 d . . .
C9 C 0.45676(14) 0.16581(14) 0.2448(3) 0.0504(5) Uani 1 1 d . . .
H9 H 0.4410 0.1906 0.3730 0.061 Uiso 1 1 calc R . .
C10 C 0.38250(15) 0.14344(15) 0.0709(3) 0.0531(5) Uani 1 1 d . . .
N4 N 0.27356(14) 0.15689(14) 0.0967(4) 0.0659(5) Uani 1 1 d . . .
O3 O 0.25532(13) 0.20129(14) 0.2494(4) 0.0868(6) Uani 1 1 d . . .
O4 O 0.20595(12) 0.12213(14) -0.0377(3) 0.0844(6) Uani 1 1 d . . .
C11 C 0.40429(17) 0.10783(15) -0.1280(4) 0.0589(6) Uani 1 1 d . . .
H11 H 0.3498 0.0948 -0.2411 0.071 Uiso 1 1 calc R . .
C12 C 0.50385(16) 0.09247(15) -0.1560(3) 0.0557(5) Uani 1 1 d . . .
H12 H 0.5187 0.0697 -0.2873 0.067 Uiso 1 1 calc R . .
C13 C 0.58410(15) 0.11221(13) 0.0206(3) 0.0472(5) Uani 1 1 d . . .
N3 N 0.68721(13) 0.09950(12) 0.0404(3) 0.0512(4) Uani 1 1 d . . .


_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 1.202(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.474(3) . ?
C2 C3 1.393(3) . ?
C2 C7 1.396(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.377(3) . ?
C7 N1 1.421(2) . ?
N1 N2 1.361(2) . ?
N1 N3 1.339(2) . ?
N2 O2 1.262(2) . ?
N2 C8 1.360(2) . ?
C8 C9 1.400(3) . ?
C8 C13 1.401(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.363(3) . ?
C10 N4 1.469(3) . ?
C10 C11 1.413(3) . ?
N4 O3 1.217(3) . ?
N4 O4 1.227(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.358(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.411(3) . ?
C13 N3 1.343(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
O1 C1 H1 117.1 . . ?
O1 C1 C2 125.8(2) . . ?
C2 C1 H1 117.1 . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 C7 117.4(2) . . ?
C7 C2 C1 123.98(18) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.1(2) . . ?
C7 C6 H6 120.5 . . ?
C2 C7 N1 120.65(17) . . ?
C6 C7 C2 121.75(19) . . ?
C6 C7 N1 117.60(19) . . ?
N2 N1 C7 122.41(15) . . ?
N3 N1 C7 123.44(15) . . ?
N3 N1 N2 114.09(14) . . ?
O2 N2 N1 123.71(15) . . ?
O2 N2 C8 131.40(15) . . ?
C8 N2 N1 104.88(14) . . ?
N2 C8 C9 129.77(18) . . ?
N2 C8 C13 106.53(16) . . ?
C9 C8 C13 123.70(18) . . ?
C8 C9 H9 122.9 . . ?
C10 C9 C8 114.29(19) . . ?
C10 C9 H9 122.9 . . ?
C9 C10 N4 116.9(2) . . ?
C9 C10 C11 124.06(19) . . ?
C11 C10 N4 119.03(19) . . ?
O3 N4 C10 118.60(19) . . ?
O3 N4 O4 123.7(2) . . ?
O4 N4 C10 117.7(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.76(19) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 121.1 . . ?
C11 C12 C13 117.8(2) . . ?
C13 C12 H12 121.1 . . ?
C8 C13 C12 119.38(18) . . ?
N3 C13 C8 110.75(17) . . ?
N3 C13 C12 129.84(19) . . ?
N1 N3 C13 103.71(15) . . ?

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
O1 C1 C2 C3 -156.2(2) . . . . ?
O1 C1 C2 C7 17.4(4) . . . . ?
C1 C2 C3 C4 170.6(2) . . . . ?
C1 C2 C7 C6 -170.8(2) . . . . ?
C1 C2 C7 N1 9.6(3) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C2 C7 N1 N2 55.9(3) . . . . ?
C2 C7 N1 N3 -127.0(2) . . . . ?
C3 C2 C7 C6 3.0(3) . . . . ?
C3 C2 C7 N1 -176.68(19) . . . . ?
C3 C4 C5 C6 1.6(4) . . . . ?
C4 C5 C6 C7 -2.1(4) . . . . ?
C5 C6 C7 C2 -0.3(4) . . . . ?
C5 C6 C7 N1 179.4(2) . . . . ?
C6 C7 N1 N2 -123.8(2) . . . . ?
C6 C7 N1 N3 53.4(3) . . . . ?
C7 C2 C3 C4 -3.5(3) . . . . ?
C7 N1 N2 O2 -1.1(3) . . . . ?
C7 N1 N2 C8 179.65(18) . . . . ?
C7 N1 N3 C13 -178.85(19) . . . . ?
N1 N2 C8 C9 176.7(2) . . . . ?
N1 N2 C8 C13 -2.0(2) . . . . ?
N2 N1 N3 C13 -1.5(2) . . . . ?
N2 C8 C9 C10 -177.5(2) . . . . ?
N2 C8 C13 C12 179.38(19) . . . . ?
N2 C8 C13 N3 1.2(2) . . . . ?
O2 N2 C8 C9 -2.4(4) . . . . ?
O2 N2 C8 C13 178.9(2) . . . . ?
C8 C9 C10 N4 177.56(19) . . . . ?
C8 C9 C10 C11 -1.8(3) . . . . ?
C8 C13 N3 N1 0.1(2) . . . . ?
C9 C8 C13 C12 0.5(3) . . . . ?
C9 C8 C13 N3 -177.6(2) . . . . ?
C9 C10 N4 O3 13.6(3) . . . . ?
C9 C10 N4 O4 -166.1(2) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
N4 C10 C11 C12 -178.4(2) . . . . ?
C11 C10 N4 O3 -167.0(2) . . . . ?
C11 C10 N4 O4 13.3(3) . . . . ?
C11 C12 C13 C8 -1.4(3) . . . . ?
C11 C12 C13 N3 176.3(2) . . . . ?
C12 C13 N3 N1 -177.8(2) . . . . ?
C13 C8 C9 C10 1.0(3) . . . . ?
N3 N1 N2 O2 -178.51(18) . . . . ?
N3 N1 N2 C8 2.3(2) . . . . ?


