# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24dnan_298
_database_code_depnum_ccdc_archive 'CCDC 1041029'
_audit_update_record             
;
2014-12-26 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2,4-dinitroanisole
_chemical_name_common            ?
_chemical_melting_point          306.6
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   3.980(2)
_cell_length_b                   13.759(7)
_cell_length_c                   15.461(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.994(8)
_cell_angle_gamma                90.00
_cell_volume                     846.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1713
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_min  0.9735
_exptl_absorpt_correction_T_max  0.9735


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+
;
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9779
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.46
_reflns_number_total             1936
_reflns_number_gt                1327
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Yadokari-XG 2009 (Kabuto, 2009), ORTEP-3 (Farrugia, 1997) & Mercury (Macrae et
al., 2006)
;

_computing_publication_material  
'PLATON (Speak, 2009) and publCIF (Westrip, 2010)'


_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1132P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1936
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1780
_refine_ls_wR_factor_gt          0.1541
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.1357(4) 0.30541(11) 0.42324(10) 0.0598(4) Uani 1 1 d . . .
C2 C 0.0128(4) 0.24011(11) 0.48530(9) 0.0560(4) Uani 1 1 d . A .
C3 C -0.1232(4) 0.15159(12) 0.46235(10) 0.0567(4) Uani 1 1 d . . .
H1 H -0.200(5) 0.1094(14) 0.5016(14) 0.075(5) Uiso 1 1 d . . .
C4 C -0.1360(4) 0.12655(12) 0.37593(10) 0.0595(4) Uani 1 1 d . B .
C5 C -0.0179(4) 0.18857(14) 0.31303(11) 0.0693(5) Uani 1 1 d . . .
H2 H -0.034(4) 0.1661(13) 0.2514(13) 0.077(5) Uiso 1 1 d . . .
C6 C 0.1169(5) 0.27686(14) 0.33669(11) 0.0703(5) Uani 1 1 d . . .
H3 H 0.187(5) 0.3161(15) 0.2924(14) 0.081(5) Uiso 1 1 d . . .
C7 C 0.3834(7) 0.45779(19) 0.3872(2) 0.0936(7) Uani 1 1 d . . .
H5 H 0.461(8) 0.508(2) 0.418(2) 0.126(10) Uiso 1 1 d . . .
H4 H 0.198(7) 0.4795(18) 0.3443(19) 0.114(8) Uiso 1 1 d . . .
H6 H 0.560(7) 0.4259(19) 0.3473(17) 0.110(8) Uiso 1 1 d . . .
N1 N 0.0236(5) 0.26307(11) 0.57796(9) 0.0736(5) Uani 1 1 d . . .
N2 N -0.2838(4) 0.03390(12) 0.35117(10) 0.0758(5) Uani 1 1 d . . .
O1 O 0.2600(3) 0.39076(9) 0.45055(8) 0.0799(4) Uani 1 1 d . . .
O2' O 0.276(2) 0.3056(7) 0.6007(2) 0.111(3) Uani 0.496(12) 1 d P A 2
O3' O -0.216(2) 0.2398(7) 0.6161(4) 0.119(3) Uani 0.496(12) 1 d P A 2
O2 O 0.065(3) 0.3432(3) 0.6066(2) 0.102(2) Uani 0.504(12) 1 d P A 1
O3 O -0.020(2) 0.1946(3) 0.63232(19) 0.0942(19) Uani 0.504(12) 1 d P A 1
O4 O -0.442(6) -0.0093(13) 0.4018(10) 0.094(4) Uani 0.59(5) 1 d P B 4
O5 O -0.263(5) 0.0075(11) 0.2763(5) 0.111(3) Uani 0.59(5) 1 d P B 4
O4' O -0.319(7) -0.0310(10) 0.4130(8) 0.089(3) Uani 0.41(5) 1 d P B 3
O5' O -0.333(6) 0.0192(16) 0.2752(9) 0.116(5) Uani 0.41(5) 1 d P B 3


_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 O1 1.340(2) . ?
C1 C6 1.395(2) . ?
C1 C2 1.408(2) . ?
C2 C3 1.377(2) . ?
C2 N1 1.467(2) . ?
C3 C4 1.380(2) . ?
C3 H1 0.90(2) . ?
C4 C5 1.382(2) . ?
C4 N2 1.452(2) . ?
C5 C6 1.375(3) . ?
C5 H2 1.002(19) . ?
C6 H3 0.92(2) . ?
C7 O1 1.438(2) . ?
C7 H5 0.89(3) . ?
C7 H4 1.03(3) . ?
C7 H6 1.04(3) . ?
N1 O3' 1.176(4) . ?
N1 O2 1.199(4) . ?
N1 O2' 1.210(4) . ?
N1 O3 1.277(4) . ?
N2 O4 1.176(9) . ?
N2 O5' 1.205(12) . ?
N2 O5 1.218(9) . ?
N2 O4' 1.317(12) . ?

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 C6 124.22(14) . . ?
O1 C1 C2 118.38(14) . . ?
C6 C1 C2 117.40(15) . . ?
C3 C2 C1 121.90(14) . . ?
C3 C2 N1 116.54(12) . . ?
C1 C2 N1 121.56(14) . . ?
C2 C3 C4 118.56(14) . . ?
C2 C3 H1 122.3(12) . . ?
C4 C3 H1 119.1(12) . . ?
C3 C4 C5 121.32(15) . . ?
C3 C4 N2 118.84(14) . . ?
C5 C4 N2 119.83(14) . . ?
C6 C5 C4 119.61(15) . . ?
C6 C5 H2 122.9(10) . . ?
C4 C5 H2 117.5(10) . . ?
C5 C6 C1 121.20(15) . . ?
C5 C6 H3 116.3(13) . . ?
C1 C6 H3 122.5(13) . . ?
O1 C7 H5 104.3(19) . . ?
O1 C7 H4 112.2(14) . . ?
H5 C7 H4 111(2) . . ?
O1 C7 H6 112.1(14) . . ?
H5 C7 H6 114(3) . . ?
H4 C7 H6 103(2) . . ?
O3' N1 O2' 131.6(4) . . ?
O2 N1 O3 117.1(3) . . ?
O3' N1 C2 114.9(3) . . ?
O2 N1 C2 124.1(2) . . ?
O2' N1 C2 113.4(3) . . ?
O3 N1 C2 118.8(2) . . ?
O4 N2 O5 121.9(6) . . ?
O5' N2 O4' 125.1(10) . . ?
O4 N2 C4 119.2(4) . . ?
O5' N2 C4 117.6(8) . . ?
O5 N2 C4 118.6(5) . . ?
O4' N2 C4 116.8(6) . . ?
C1 O1 C7 118.43(17) . . ?

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 179.04(13) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
O1 C1 C2 N1 -1.0(2) . . . . ?
C6 C1 C2 N1 179.57(15) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
N1 C2 C3 C4 -179.47(14) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C2 C3 C4 N2 -179.09(13) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
N2 C4 C5 C6 178.97(15) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
O1 C1 C6 C5 -179.13(15) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C3 C2 N1 O3' -40.2(7) . . . . ?
C1 C2 N1 O3' 139.8(7) . . . . ?
C3 C2 N1 O2 -163.3(6) . . . . ?
C1 C2 N1 O2 16.7(7) . . . . ?
C3 C2 N1 O2' 141.9(6) . . . . ?
C1 C2 N1 O2' -38.1(6) . . . . ?
C3 C2 N1 O3 15.2(5) . . . . ?
C1 C2 N1 O3 -164.8(5) . . . . ?
C3 C4 N2 O4 13.7(17) . . . . ?
C5 C4 N2 O4 -164.9(17) . . . . ?
C3 C4 N2 O5' 170.3(15) . . . . ?
C5 C4 N2 O5' -8.4(15) . . . . ?
C3 C4 N2 O5 -172.4(12) . . . . ?
C5 C4 N2 O5 9.0(12) . . . . ?
C3 C4 N2 O4' -16.9(15) . . . . ?
C5 C4 N2 O4' 164.5(15) . . . . ?
C6 C1 O1 C7 -0.2(3) . . . . ?
C2 C1 O1 C7 -179.58(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C3 H1 O4 0.90(2) 2.50(3) 3.371(19) 165.1(18) 3_456 yes
C7 H4 O5 1.03(3) 2.55(3) 3.569(15) 170(2) 2_455 yes
C7 H6 O5 1.04(3) 2.37(3) 3.045(13) 121.4(19) 2_555 yes

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrystalClear (Rigaku Americas and Rigaku,2009)
;
_chemical_absolute_configuration ?


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24dnan_283K
_database_code_depnum_ccdc_archive 'CCDC 1041030'
_audit_update_record             
;
2014-12-26 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2,4-dinitroanisole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   3.9618(19)
_cell_length_b                   13.745(7)
_cell_length_c                   15.470(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.089(6)
_cell_angle_gamma                90.00
_cell_volume                     842.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    283(2)
_cell_measurement_reflns_used    1808
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_min  0.9733
_exptl_absorpt_correction_T_max  0.9733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;CrystalClear (Rigaku Americas and Rigaku, 2009)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      283(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+
;
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4520
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.50
_reflns_number_total             1915
_reflns_number_gt                1087
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Yadokari-XG 2009 (Kabuto, 2009), ORTEP-3 (Farrugia, 1997) & Mercury (Macrae et
al., 2006)
;

_computing_publication_material  
'PLATON (Speak, 2009) and publCIF (Westrip, 2010)'


_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0768P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1915
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1241
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_restrained_S_all      0.883
_refine_ls_shift/su_max          0.002
_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 1.1351(4) 0.30563(11) 0.42366(9) 0.0538(4) Uani 1 1 d . . .
C2 C 1.0130(4) 0.24001(11) 0.48557(8) 0.0497(4) Uani 1 1 d . A .
C3 C 0.8779(4) 0.15163(12) 0.46260(9) 0.0512(4) Uani 1 1 d . . .
H1 H 0.787(4) 0.1104(12) 0.5025(11) 0.067(5) Uiso 1 1 d . . .
C4 C 0.8651(4) 0.12629(11) 0.37617(9) 0.0528(4) Uani 1 1 d . B .
C5 C 0.9840(4) 0.18853(13) 0.31338(10) 0.0625(5) Uani 1 1 d . . .
H2 H 0.965(4) 0.1683(11) 0.2514(11) 0.070(4) Uiso 1 1 d . . .
C6 C 1.1171(4) 0.27675(14) 0.33697(10) 0.0631(5) Uani 1 1 d . . .
H3 H 1.188(4) 0.3175(14) 0.2953(12) 0.079(5) Uiso 1 1 d . . .
C7 C 1.3845(7) 0.45822(18) 0.38747(17) 0.0842(7) Uani 1 1 d . . .
H6 H 1.564(7) 0.4265(18) 0.3501(16) 0.125(9) Uiso 1 1 d . . .
H5 H 1.475(6) 0.5112(17) 0.4204(15) 0.108(7) Uiso 1 1 d . . .
H4 H 1.203(5) 0.4766(15) 0.3459(15) 0.105(7) Uiso 1 1 d . . .
N1 N 1.0218(4) 0.26323(11) 0.57819(9) 0.0662(4) Uani 1 1 d . . .
N2 N 0.7188(4) 0.03340(11) 0.35135(9) 0.0686(4) Uani 1 1 d . . .
O1 O 1.2588(3) 0.39108(9) 0.45089(7) 0.0726(4) Uani 1 1 d . . .
O2 O 1.062(3) 0.3436(3) 0.6070(2) 0.0901(19) Uani 0.493(12) 1 d P A 1
O3 O 0.977(2) 0.1948(3) 0.63284(18) 0.0852(19) Uani 0.493(12) 1 d P A 1
O4 O 0.692(6) -0.0335(11) 0.4128(7) 0.072(3) Uani 0.34(5) 1 d P B 3
O5 O 0.666(6) 0.0207(16) 0.2760(8) 0.103(4) Uani 0.34(5) 1 d P B 3
O2' O 1.270(2) 0.3076(7) 0.6015(2) 0.101(2) Uani 0.507(12) 1 d P A 2
O3' O 0.783(2) 0.2395(7) 0.6165(3) 0.109(3) Uani 0.507(12) 1 d P A 2
O4' O 0.566(5) -0.0112(11) 0.4035(7) 0.087(3) Uani 0.66(5) 1 d P B 4
O5' O 0.734(4) 0.0066(9) 0.2759(4) 0.104(2) Uani 0.66(5) 1 d P B 4


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.3375(19) . ?
C1 C6 1.399(2) . ?
C1 C2 1.408(2) . ?
C2 C3 1.372(2) . ?
C2 N1 1.4678(19) . ?
C3 C4 1.382(2) . ?
C3 H1 0.917(18) . ?
C4 C5 1.384(2) . ?
C4 N2 1.451(2) . ?
C5 C6 1.369(2) . ?
C5 H2 0.999(17) . ?
C6 H3 0.903(19) . ?
C7 O1 1.443(2) . ?
C7 H6 1.02(3) . ?
C7 H5 0.96(3) . ?
C7 H4 0.99(2) . ?
N1 O3' 1.172(4) . ?
N1 O2 1.201(4) . ?
N1 O2' 1.207(4) . ?
N1 O3 1.280(4) . ?
N2 O4' 1.189(7) . ?
N2 O5 1.193(11) . ?
N2 O5' 1.227(7) . ?
N2 O4 1.327(13) . ?

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 C6 124.25(14) . . ?
O1 C1 C2 118.48(13) . . ?
C6 C1 C2 117.27(15) . . ?
C3 C2 C1 121.92(13) . . ?
C3 C2 N1 116.58(13) . . ?
C1 C2 N1 121.50(14) . . ?
C2 C3 C4 118.74(14) . . ?
C2 C3 H1 122.0(10) . . ?
C4 C3 H1 119.2(10) . . ?
C3 C4 C5 121.11(15) . . ?
C3 C4 N2 119.02(14) . . ?
C5 C4 N2 119.86(14) . . ?
C6 C5 C4 119.67(15) . . ?
C6 C5 H2 121.6(9) . . ?
C4 C5 H2 118.7(9) . . ?
C5 C6 C1 121.29(16) . . ?
C5 C6 H3 118.8(11) . . ?
C1 C6 H3 119.8(11) . . ?
O1 C7 H6 111.4(14) . . ?
O1 C7 H5 104.9(13) . . ?
H6 C7 H5 112(2) . . ?
O1 C7 H4 110.5(13) . . ?
H6 C7 H4 104.2(19) . . ?
H5 C7 H4 114.5(18) . . ?
O2 N1 O3 116.8(3) . . ?
O3' N1 C2 115.3(2) . . ?
O2 N1 C2 124.3(2) . . ?
O2' N1 C2 114.0(3) . . ?
O3 N1 C2 118.95(18) . . ?
O5 N2 O4 125.7(10) . . ?
O4' N2 C4 118.8(3) . . ?
O5 N2 C4 116.6(8) . . ?
O5' N2 C4 119.3(4) . . ?
O4 N2 C4 117.2(5) . . ?
C1 O1 C7 118.47(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 179.04(13) . . . . ?
C6 C1 C2 C3 -0.7(2) . . . . ?
O1 C1 C2 N1 -0.5(2) . . . . ?
C6 C1 C2 N1 179.75(15) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
N1 C2 C3 C4 -179.76(13) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C2 C3 C4 N2 -179.28(13) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
N2 C4 C5 C6 179.00(15) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
O1 C1 C6 C5 -179.30(14) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
C3 C2 N1 O3' -39.7(7) . . . . ?
C1 C2 N1 O3' 139.9(7) . . . . ?
C3 C2 N1 O2 -163.2(6) . . . . ?
C1 C2 N1 O2 16.4(7) . . . . ?
C3 C2 N1 O2' 143.3(6) . . . . ?
C1 C2 N1 O2' -37.1(6) . . . . ?
C3 C2 N1 O3 15.3(5) . . . . ?
C1 C2 N1 O3 -165.2(5) . . . . ?
C3 C4 N2 O4' 12.0(15) . . . . ?
C5 C4 N2 O4' -166.9(15) . . . . ?
C3 C4 N2 O5 169.0(15) . . . . ?
C5 C4 N2 O5 -9.9(15) . . . . ?
C3 C4 N2 O5' -173.5(9) . . . . ?
C5 C4 N2 O5' 7.5(10) . . . . ?
C3 C4 N2 O4 -18.5(13) . . . . ?
C5 C4 N2 O4 162.5(13) . . . . ?
C6 C1 O1 C7 -0.4(3) . . . . ?
C2 C1 O1 C7 179.89(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C3 H1 O4' 0.917(17) 2.45(2) 3.354(15) 168.3(14) 3_656 yes
C5 H2 O2' 1.000(17) 2.453(17) 3.370(4) 152.4(12) 4_454 yes
C7 H4 O5' 0.99(2) 2.57(2) 3.549(12) 172.1(18) 2_655 yes
C7 H6 O5' 1.02(3) 2.39(3) 3.043(10) 120.8(18) 2_755 yes


_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.036
_chemical_absolute_configuration ?



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24dnan_273K
_database_code_depnum_ccdc_archive 'CCDC 1041031'
_audit_update_record             
;
2014-12-26 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   3.957(2)
_cell_length_b                   13.735(7)
_cell_length_c                   15.454(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.156(8)
_cell_angle_gamma                90.00
_cell_volume                     839.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2000
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9733
_exptl_absorpt_correction_T_max  0.9733
_exptl_absorpt_process_details   
;CrystalClear (Rigaku Americas and Rigaku, 2009)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+
;
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3814
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.25
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1904
_reflns_number_gt                1178
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Yadokari-XG 2009 (Kabuto, 2009), ORTEP-3 (Farrugia, 1997) & Mercury (Macrae et
al., 2006)
;

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1904
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1522
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   0.887
_refine_ls_restrained_S_all      0.887
_refine_ls_shift/su_max          0.002
_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 0.3650(4) 0.30558(12) 0.07634(11) 0.0510(4) Uani 1 1 d . . .
C2 C 0.4871(4) 0.24006(12) 0.01451(10) 0.0472(4) Uani 1 1 d . A .
C3 C 0.6232(4) 0.15150(13) 0.03747(10) 0.0477(4) Uani 1 1 d . . .
H1 H 0.708(5) 0.1105(14) -0.0014(13) 0.059(5) Uiso 1 1 d . . .
C4 C 0.6341(4) 0.12631(12) 0.12368(10) 0.0495(4) Uani 1 1 d . B .
C5 C 0.5155(5) 0.18839(14) 0.18668(11) 0.0592(5) Uani 1 1 d . . .
H2 H 0.538(5) 0.1652(15) 0.2487(15) 0.077(6) Uiso 1 1 d . . .
C6 C 0.3821(5) 0.27693(15) 0.16292(12) 0.0593(5) Uani 1 1 d . . .
H3 H 0.299(5) 0.3186(16) 0.2050(14) 0.068(6) Uiso 1 1 d . . .
C7 C 0.1151(8) 0.45802(19) 0.11268(19) 0.0794(7) Uani 1 1 d . . .
H6 H -0.061(8) 0.424(2) 0.1506(19) 0.115(10) Uiso 1 1 d . . .
H5 H 0.029(8) 0.511(2) 0.0830(19) 0.111(9) Uiso 1 1 d . . .
H4 H 0.298(7) 0.4782(19) 0.1540(19) 0.106(8) Uiso 1 1 d . . .
N1 N 0.4788(5) 0.26339(12) -0.07840(10) 0.0621(5) Uani 1 1 d . . .
N2 N 0.7811(5) 0.03304(12) 0.14883(11) 0.0645(5) Uani 1 1 d . . .
O1 O 0.2412(4) 0.39131(9) 0.04911(8) 0.0677(4) Uani 1 1 d . . .
O2 O 0.437(3) 0.3433(3) -0.1075(2) 0.0844(19) Uani 0.498(12) 1 d P A 1
O3 O 0.527(2) 0.1950(3) -0.1331(2) 0.080(2) Uani 0.498(12) 1 d P A 1
O2' O 0.229(2) 0.3079(6) -0.1016(2) 0.095(3) Uani 0.502(12) 1 d P A 2
O3' O 0.720(2) 0.2399(7) -0.1161(4) 0.103(3) Uani 0.502(12) 1 d P A 2
O5' O 0.744(7) 0.0029(15) 0.2234(8) 0.095(4) Uani 0.46(5) 1 d P B 4
O4' O 0.958(7) -0.0075(14) 0.0984(11) 0.074(3) Uani 0.46(5) 1 d P B 4
O4 O 0.832(7) -0.0288(12) 0.0889(6) 0.079(3) Uani 0.54(5) 1 d P B 3
O5 O 0.823(5) 0.0181(13) 0.2247(7) 0.094(3) Uani 0.54(5) 1 d P B 3


_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 O1 1.340(2) . ?
C1 C6 1.395(3) . ?
C1 C2 1.405(2) . ?
C2 C3 1.374(2) . ?
C2 N1 1.471(2) . ?
C3 C4 1.376(2) . ?
C3 H1 0.89(2) . ?
C4 C5 1.383(2) . ?
C4 N2 1.456(2) . ?
C5 C6 1.373(3) . ?
C5 H2 1.01(2) . ?
C6 H3 0.93(2) . ?
C7 O1 1.440(3) . ?
C7 H6 1.03(3) . ?
C7 H5 0.92(3) . ?
C7 H4 0.99(3) . ?
N1 O3' 1.173(4) . ?
N1 O2 1.196(4) . ?
N1 O2' 1.209(4) . ?
N1 O3 1.280(4) . ?
N2 O4' 1.195(10) . ?
N2 O5 1.199(10) . ?
N2 O5' 1.236(12) . ?
N2 O4 1.276(11) . ?

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 C6 124.01(15) . . ?
O1 C1 C2 118.55(15) . . ?
C6 C1 C2 117.44(16) . . ?
C3 C2 C1 121.99(15) . . ?
C3 C2 N1 116.48(13) . . ?
C1 C2 N1 121.53(15) . . ?
C2 C3 C4 118.49(15) . . ?
C2 C3 H1 122.3(12) . . ?
C4 C3 H1 119.1(12) . . ?
C3 C4 C5 121.45(16) . . ?
C3 C4 N2 118.95(15) . . ?
C5 C4 N2 119.59(15) . . ?
C6 C5 C4 119.47(16) . . ?
C6 C5 H2 123.9(12) . . ?
C4 C5 H2 116.6(12) . . ?
C5 C6 C1 121.15(17) . . ?
C5 C6 H3 119.8(13) . . ?
C1 C6 H3 119.1(13) . . ?
O1 C7 H6 110.3(15) . . ?
O1 C7 H5 106.9(18) . . ?
H6 C7 H5 113(3) . . ?
O1 C7 H4 110.9(15) . . ?
H6 C7 H4 105(2) . . ?
H5 C7 H4 111(2) . . ?
O3' N1 O2' 131.2(5) . . ?
O2 N1 O3 116.5(3) . . ?
O3' N1 C2 115.0(3) . . ?
O2 N1 C2 124.5(2) . . ?
O2' N1 C2 113.6(3) . . ?
O3 N1 C2 119.0(2) . . ?
O4' N2 O5' 122.2(9) . . ?
O5 N2 O4 125.1(8) . . ?
O4' N2 C4 118.2(5) . . ?
O5 N2 C4 117.3(6) . . ?
O5' N2 C4 119.3(7) . . ?
O4 N2 C4 117.4(5) . . ?
C1 O1 C7 118.33(17) . . ?

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 178.87(16) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
O1 C1 C2 N1 -0.5(3) . . . . ?
C6 C1 C2 N1 179.74(17) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
N1 C2 C3 C4 -179.57(15) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C2 C3 C4 N2 -179.35(15) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
N2 C4 C5 C6 178.95(17) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
O1 C1 C6 C5 -179.28(16) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C3 C2 N1 O3' -39.9(7) . . . . ?
C1 C2 N1 O3' 139.4(7) . . . . ?
C3 C2 N1 O2 -163.5(6) . . . . ?
C1 C2 N1 O2 15.9(7) . . . . ?
C3 C2 N1 O2' 143.4(6) . . . . ?
C1 C2 N1 O2' -37.2(6) . . . . ?
C3 C2 N1 O3 14.8(6) . . . . ?
C1 C2 N1 O3 -165.8(5) . . . . ?
C3 C4 N2 O4' 17.7(18) . . . . ?
C5 C4 N2 O4' -160.9(18) . . . . ?
C3 C4 N2 O5 171.5(14) . . . . ?
C5 C4 N2 O5 -7.2(14) . . . . ?
C3 C4 N2 O5' -168.5(16) . . . . ?
C5 C4 N2 O5' 12.8(17) . . . . ?
C3 C4 N2 O4 -13.4(16) . . . . ?
C5 C4 N2 O4 168.0(15) . . . . ?
C6 C1 O1 C7 -0.5(3) . . . . ?
C2 C1 O1 C7 179.75(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C3 H1 O4 0.89(2) 2.41(2) 2.724(18) 100.7(15) . yes
C3 H1 O4 0.89(2) 2.55(3) 3.39(2) 156.3(17) 3_755 yes
C5 H2 O2' 1.01(2) 2.45(2) 3.363(4) 150.1(16) 4_555 yes
C7 H4 O5 1.00(3) 2.44(3) 3.423(16) 170(2) 2_655 yes
C7 H6 O5 1.03(3) 2.56(3) 3.190(15) 119(2) 2_555 yes


_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.033
_chemical_absolute_configuration ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24dnan_261K
_database_code_depnum_ccdc_archive 'CCDC 1041032'
_audit_update_record             
;
2014-12-26 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   3.9291(18)
_cell_length_b                   13.739(6)
_cell_length_c                   15.443(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.454(7)
_cell_angle_gamma                90.00
_cell_volume                     831.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    261(2)
_cell_measurement_reflns_used    1951
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9730
_exptl_absorpt_correction_T_max  0.9730
_exptl_absorpt_process_details   
;CrystalClear (Rigaku Americas and Rigaku, 2009)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      261(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+
;
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3742
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.45
_reflns_number_total             1865
_reflns_number_gt                1160
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Yadokari-XG 2009 (Kabuto, 2009), ORTEP-3 (Farrugia, 1997) & Mercury (Macrae et
al., 2006)
;

_computing_publication_material  
'PLATON (Speak, 2009) and publCIF (Westrip, 2010)'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0691P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1865
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1216
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_restrained_S_all      0.919
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.002

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 -0.1085(4) 0.31402(11) 0.42559(9) 0.0432(4) Uani 1 1 d . . .
C2 C -0.0197(4) 0.24159(11) 0.48714(9) 0.0426(4) Uani 1 1 d . A .
C3 C 0.1130(4) 0.15356(13) 0.46399(10) 0.0459(4) Uani 1 1 d . . .
H1 H 0.175(4) 0.1071(15) 0.5036(12) 0.067(6) Uiso 1 1 d . . .
C4 C 0.1562(4) 0.13675(12) 0.37749(9) 0.0455(4) Uani 1 1 d . . .
C5 C 0.0736(4) 0.20605(14) 0.31512(10) 0.0531(5) Uani 1 1 d . . .
H2 H 0.101(4) 0.1881(12) 0.2563(11) 0.056(5) Uiso 1 1 d . . .
C6 C -0.0578(4) 0.29364(13) 0.33880(10) 0.0517(4) Uani 1 1 d . . .
H3 H -0.108(4) 0.3413(13) 0.2939(12) 0.063(5) Uiso 1 1 d . . .
C7 C -0.3182(7) 0.47323(17) 0.39026(15) 0.0655(6) Uani 1 1 d . . .
H6 H -0.121(6) 0.4918(15) 0.3613(14) 0.084(7) Uiso 1 1 d . . .
H5 H -0.407(6) 0.5229(19) 0.4202(15) 0.096(8) Uiso 1 1 d . . .
H4 H -0.473(5) 0.4502(14) 0.3452(15) 0.080(7) Uiso 1 1 d . . .
N1 N -0.0626(4) 0.25551(12) 0.58006(9) 0.0566(4) Uani 1 1 d . . .
N2 N 0.3003(4) 0.04389(12) 0.35291(10) 0.0607(4) Uani 1 1 d . . .
O1 O -0.2317(3) 0.39864(8) 0.45260(7) 0.0572(4) Uani 1 1 d . . .
O2 O -0.311(2) 0.3058(11) 0.5960(7) 0.070(2) Uani 0.53(4) 1 d P A 1
O3 O 0.144(5) 0.2169(15) 0.6310(8) 0.108(4) Uani 0.53(4) 1 d P A 1
O4 O 0.3511(5) -0.01841(12) 0.40811(10) 0.1057(6) Uani 1 1 d . . .
O5 O 0.3637(4) 0.03183(12) 0.27821(9) 0.0952(6) Uani 1 1 d . . .
O2' O -0.184(9) 0.3264(11) 0.6086(8) 0.093(5) Uani 0.47(4) 1 d P A 2
O3' O 0.039(5) 0.1933(10) 0.6302(7) 0.079(3) Uani 0.47(4) 1 d P A 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 O1 1.3383(19) . ?
C1 C6 1.399(2) . ?
C1 C2 1.401(2) . ?
C2 C3 1.375(2) . ?
C2 N1 1.470(2) . ?
C3 C4 1.379(2) . ?
C3 H1 0.90(2) . ?
C4 C5 1.375(2) . ?
C4 N2 1.458(2) . ?
C5 C6 1.370(3) . ?
C5 H2 0.956(17) . ?
C6 H3 0.964(18) . ?
C7 O1 1.429(2) . ?
C7 H6 0.96(2) . ?
C7 H5 0.91(3) . ?
C7 H4 0.94(2) . ?
N1 O2' 1.184(11) . ?
N1 O3' 1.201(10) . ?
N1 O3 1.209(11) . ?
N1 O2 1.236(10) . ?
N2 O5 1.2102(19) . ?
N2 O4 1.214(2) . ?

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 C6 123.67(14) . . ?
O1 C1 C2 118.85(13) . . ?
C6 C1 C2 117.47(15) . . ?
C3 C2 C1 121.85(14) . . ?
C3 C2 N1 116.26(13) . . ?
C1 C2 N1 121.88(14) . . ?
C2 C3 C4 118.48(15) . . ?
C2 C3 H1 122.2(12) . . ?
C4 C3 H1 119.4(12) . . ?
C5 C4 C3 121.49(16) . . ?
C5 C4 N2 119.92(14) . . ?
C3 C4 N2 118.58(15) . . ?
C6 C5 C4 119.64(15) . . ?
C6 C5 H2 123.6(10) . . ?
C4 C5 H2 116.7(10) . . ?
C5 C6 C1 121.07(16) . . ?
C5 C6 H3 117.8(11) . . ?
C1 C6 H3 121.1(11) . . ?
O1 C7 H6 110.3(12) . . ?
O1 C7 H5 106.1(14) . . ?
H6 C7 H5 113(2) . . ?
O1 C7 H4 111.3(12) . . ?
H6 C7 H4 104.0(18) . . ?
H5 C7 H4 112.3(19) . . ?
O2' N1 O3' 117.9(7) . . ?
O2' N1 O3 112.8(11) . . ?
O3' N1 O3 25.1(10) . . ?
O2' N1 O2 28.3(12) . . ?
O3' N1 O2 119.8(8) . . ?
O3 N1 O2 128.0(9) . . ?
O2' N1 C2 123.4(6) . . ?
O3' N1 C2 118.6(5) . . ?
O3 N1 C2 117.2(7) . . ?
O2 N1 C2 114.8(5) . . ?
O5 N2 O4 122.56(16) . . ?
O5 N2 C4 118.74(16) . . ?
O4 N2 C4 118.70(14) . . ?
C1 O1 C7 119.07(14) . . ?

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 -179.03(15) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
O1 C1 C2 N1 0.9(2) . . . . ?
C6 C1 C2 N1 180.00(15) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
N1 C2 C3 C4 179.62(13) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C2 C3 C4 N2 179.35(14) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
N2 C4 C5 C6 -179.22(15) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
O1 C1 C6 C5 179.11(15) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C3 C2 N1 O2' -178(2) . . . . ?
C1 C2 N1 O2' 3(2) . . . . ?
C3 C2 N1 O3' 4.8(12) . . . . ?
C1 C2 N1 O3' -175.1(12) . . . . ?
C3 C2 N1 O3 33.2(14) . . . . ?
C1 C2 N1 O3 -146.7(13) . . . . ?
C3 C2 N1 O2 -146.5(8) . . . . ?
C1 C2 N1 O2 33.6(8) . . . . ?
C5 C4 N2 O5 4.4(2) . . . . ?
C3 C4 N2 O5 -174.22(16) . . . . ?
C5 C4 N2 O4 -175.43(17) . . . . ?
C3 C4 N2 O4 5.9(2) . . . . ?
C6 C1 O1 C7 0.1(3) . . . . ?
C2 C1 O1 C7 179.14(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C3 H1 O4 0.90(2) 2.533(18) 3.337(3) 148.4(14) 3_656 yes
C5 H2 O5 0.955(17) 2.395(16) 2.730(3) 100.2(11) . yes
C5 H2 O2 0.955(17) 2.53(2) 3.453(11) 163.1(14) 4_554 yes
C7 H6 O5 0.96(2) 2.51(2) 3.366(3) 148.5(18) 2_555 yes

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.037
_chemical_absolute_configuration ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24dnan_236K
_database_code_depnum_ccdc_archive 'CCDC 1041033'
_audit_update_record             
;
2014-12-26 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   3.908(2)
_cell_length_b                   13.78(1)
_cell_length_c                   15.42(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.310(6)
_cell_angle_gamma                90.00
_cell_volume                     826.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    236(2)
_cell_measurement_reflns_used    2175
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_min  0.9729
_exptl_absorpt_correction_T_max  0.9729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;CrystalClear (Rigaku Americas and Rigaku, 2009)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      236(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+
;
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3739
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.49
_reflns_number_total             1861
_reflns_number_gt                1123
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Yadokari-XG 2009 (Kabuto, 2009), ORTEP-3 (Farrugia, 1997) & Mercury (Macrae et
al., 2006)
;

_computing_publication_material  
'PLATON (Speak, 2009) and publCIF (Westrip, 2010)'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0665P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1861
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1255
_refine_ls_wR_factor_gt          0.1147
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_restrained_S_all      0.917
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.002

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 0.3951(4) 0.31522(12) 0.92609(10) 0.0361(4) Uani 1 1 d . . .
C2 C 0.4797(4) 0.24180(11) 0.98757(9) 0.0354(4) Uani 1 1 d . . .
C3 C 0.6115(5) 0.15396(13) 0.96464(11) 0.0382(4) Uani 1 1 d . . .
H1 H 0.663(4) 0.1069(14) 1.0062(12) 0.045(5) Uiso 1 1 d . . .
C4 C 0.6588(4) 0.13803(12) 0.87834(11) 0.0388(4) Uani 1 1 d . . .
C5 C 0.5813(5) 0.20805(14) 0.81561(11) 0.0446(5) Uani 1 1 d . . .
H2 H 0.618(5) 0.1952(13) 0.7557(12) 0.046(5) Uiso 1 1 d . . .
C6 C 0.4507(5) 0.29570(14) 0.83942(11) 0.0432(5) Uani 1 1 d . . .
H3 H 0.402(5) 0.3432(14) 0.7962(13) 0.058(6) Uiso 1 1 d . . .
C7 C 0.1901(7) 0.47510(16) 0.89032(15) 0.0548(6) Uani 1 1 d . . .
H5 H 0.110(6) 0.5253(16) 0.9211(13) 0.062(6) Uiso 1 1 d . . .
H4 H 0.026(6) 0.4530(14) 0.8415(14) 0.065(6) Uiso 1 1 d . . .
H6 H 0.383(6) 0.4946(13) 0.8623(14) 0.061(6) Uiso 1 1 d . . .
N1 N 0.4341(4) 0.25512(11) 1.08046(9) 0.0473(4) Uani 1 1 d . . .
N2 N 0.8005(4) 0.04489(12) 0.85353(10) 0.0506(4) Uani 1 1 d . . .
O1 O 0.2721(3) 0.39981(8) 0.95309(7) 0.0476(4) Uani 1 1 d . . .
O2 O 0.2322(5) 0.31510(11) 1.10118(9) 0.0871(6) Uani 1 1 d . . .
O3 O 0.5929(5) 0.20378(13) 1.13263(9) 0.0916(6) Uani 1 1 d . . .
O4 O 0.8402(5) -0.01864(11) 0.90834(10) 0.0871(6) Uani 1 1 d . . .
O5 O 0.8765(5) 0.03440(11) 0.77946(9) 0.0791(5) 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
C1 O1 1.342(2) . ?
C1 C6 1.400(2) . ?
C1 C2 1.405(2) . ?
C2 C3 1.374(2) . ?
C2 N1 1.471(2) . ?
C3 C4 1.378(2) . ?
C3 H1 0.921(19) . ?
C4 C5 1.380(2) . ?
C4 N2 1.463(2) . ?
C5 C6 1.375(3) . ?
C5 H2 0.965(18) . ?
C6 H3 0.94(2) . ?
C7 O1 1.435(2) . ?
C7 H5 0.91(2) . ?
C7 H4 0.99(2) . ?
C7 H6 0.94(2) . ?
N1 O3 1.2001(19) . ?
N1 O2 1.206(2) . ?
N2 O5 1.215(2) . ?
N2 O4 1.217(2) . ?

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 C6 123.70(15) . . ?
O1 C1 C2 119.01(14) . . ?
C6 C1 C2 117.28(15) . . ?
C3 C2 C1 122.08(14) . . ?
C3 C2 N1 116.25(14) . . ?
C1 C2 N1 121.67(14) . . ?
C2 C3 C4 118.40(16) . . ?
C2 C3 H1 120.3(11) . . ?
C4 C3 H1 121.3(11) . . ?
C3 C4 C5 121.68(16) . . ?
C3 C4 N2 118.70(15) . . ?
C5 C4 N2 119.61(15) . . ?
C6 C5 C4 119.35(16) . . ?
C6 C5 H2 120.6(11) . . ?
C4 C5 H2 120.1(11) . . ?
C5 C6 C1 121.21(17) . . ?
C5 C6 H3 118.6(12) . . ?
C1 C6 H3 120.2(12) . . ?
O1 C7 H5 105.3(12) . . ?
O1 C7 H4 112.3(12) . . ?
H5 C7 H4 113.4(19) . . ?
O1 C7 H6 112.2(13) . . ?
H5 C7 H6 110.6(18) . . ?
H4 C7 H6 103.2(18) . . ?
O3 N1 O2 122.46(15) . . ?
O3 N1 C2 118.52(15) . . ?
O2 N1 C2 118.99(15) . . ?
O5 N2 O4 122.74(17) . . ?
O5 N2 C4 118.79(16) . . ?
O4 N2 C4 118.46(15) . . ?
C1 O1 C7 118.88(14) . . ?

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 -179.05(16) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
O1 C1 C2 N1 0.5(2) . . . . ?
C6 C1 C2 N1 179.49(17) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
N1 C2 C3 C4 179.97(15) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C2 C3 C4 N2 179.69(16) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
N2 C4 C5 C6 -179.50(17) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
O1 C1 C6 C5 179.19(17) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C3 C2 N1 O3 20.0(3) . . . . ?
C1 C2 N1 O3 -159.63(18) . . . . ?
C3 C2 N1 O2 -157.97(17) . . . . ?
C1 C2 N1 O2 22.4(3) . . . . ?
C3 C4 N2 O5 -172.29(18) . . . . ?
C5 C4 N2 O5 6.6(3) . . . . ?
C3 C4 N2 O4 7.1(3) . . . . ?
C5 C4 N2 O4 -174.00(18) . . . . ?
C6 C1 O1 C7 0.3(3) . . . . ?
C2 C1 O1 C7 179.21(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C3 H1 O4 0.921(19) 2.552(17) 3.336(3) 143.3(13) 3_757 yes
C5 H2 O2 0.964(19) 2.469(19) 3.427(3) 172.5(15) 4_554 yes
C7 H4 O5 0.99(2) 2.58(2) 3.369(4) 136.4(15) 2_556 yes
C7 H5 O2 0.91(2) 2.58(2) 3.338(4) 141.0(17) 3_567 yes
C7 H6 O5 0.94(2) 2.52(2) 3.348(4) 147.0(18) 2_656 yes


_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.040
_chemical_absolute_configuration ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24dnan_226K
_database_code_depnum_ccdc_archive 'CCDC 1041034'
_audit_update_record             
;
2014-12-26 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   3.8968(18)
_cell_length_b                   13.781(7)
_cell_length_c                   15.419(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.382(6)
_cell_angle_gamma                90.00
_cell_volume                     824.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    226(2)
_cell_measurement_reflns_used    2055
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;CrystalClear (Rigaku Americas and Rigaku, 2009)
;
_exptl_absorpt_correction_T_min  0.9728
_exptl_absorpt_correction_T_max  0.9728
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      226(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+
;
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4076
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1863
_reflns_number_gt                1293
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Yadokari-XG 2009 (Kabuto, 2009), ORTEP-3 (Farrugia, 1997) & Mercury (Macrae et
al., 2006)
;

_computing_publication_material  
'PLATON (Speak, 2009) and publCIF (Westrip, 2010)'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0745P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1863
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1396
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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 0.6041(4) 0.18437(12) 0.07367(10) 0.0346(4) Uani 1 1 d . . .
C2 C 0.5202(4) 0.25792(12) 0.01217(9) 0.0336(4) Uani 1 1 d . . .
C3 C 0.3893(4) 0.34620(13) 0.03505(10) 0.0361(4) Uani 1 1 d . . .
H1 H 0.343(5) 0.3933(15) -0.0070(12) 0.046(5) Uiso 1 1 d . . .
C4 C 0.3401(4) 0.36172(12) 0.12178(10) 0.0363(4) Uani 1 1 d . . .
C5 C 0.4163(5) 0.29163(14) 0.18441(10) 0.0417(5) Uani 1 1 d . . .
H2 H 0.382(5) 0.3050(13) 0.2456(12) 0.041(5) Uiso 1 1 d . . .
C6 C 0.5468(5) 0.20363(14) 0.16041(10) 0.0404(4) Uani 1 1 d . . .
H3 H 0.591(5) 0.1546(14) 0.2040(13) 0.054(6) Uiso 1 1 d . . .
C7 C 0.8093(6) 0.02446(16) 0.10947(14) 0.0500(5) Uani 1 1 d . . .
H6 H 0.968(7) 0.0459(16) 0.1559(15) 0.068(7) Uiso 1 1 d . . .
H5 H 0.893(6) -0.0259(16) 0.0786(13) 0.058(6) Uiso 1 1 d . . .
H4 H 0.613(7) 0.0041(15) 0.1367(14) 0.067(6) Uiso 1 1 d . . .
N1 N 0.5666(4) 0.24480(11) -0.08083(8) 0.0433(4) Uani 1 1 d . . .
N2 N 0.1982(4) 0.45480(12) 0.14610(9) 0.0479(4) Uani 1 1 d . . .
O1 O 0.7273(3) 0.09987(9) 0.04696(7) 0.0444(4) Uani 1 1 d . . .
O2 O 0.7702(5) 0.18491(12) -0.10112(9) 0.0804(6) Uani 1 1 d . . .
O3 O 0.4063(5) 0.29641(13) -0.13281(8) 0.0848(6) Uani 1 1 d . . .
O4 O 0.1630(5) 0.51874(12) 0.09167(10) 0.0808(6) Uani 1 1 d . . .
O5 O 0.1204(5) 0.46496(12) 0.22023(9) 0.0741(5) 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
C1 O1 1.339(2) . ?
C1 C6 1.402(2) . ?
C1 C2 1.405(2) . ?
C2 C3 1.378(2) . ?
C2 N1 1.4733(19) . ?
C3 C4 1.385(2) . ?
C3 H1 0.92(2) . ?
C4 C5 1.378(2) . ?
C4 N2 1.460(2) . ?
C5 C6 1.379(3) . ?
C5 H2 0.982(18) . ?
C6 H3 0.96(2) . ?
C7 O1 1.433(2) . ?
C7 H6 0.95(3) . ?
C7 H5 0.92(2) . ?
C7 H4 0.95(2) . ?
N1 O3 1.202(2) . ?
N1 O2 1.206(2) . ?
N2 O4 1.216(2) . ?
N2 O5 1.2179(18) . ?

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 C6 123.49(15) . . ?
O1 C1 C2 119.15(13) . . ?
C6 C1 C2 117.35(15) . . ?
C3 C2 C1 122.16(13) . . ?
C3 C2 N1 116.09(14) . . ?
C1 C2 N1 121.75(14) . . ?
C2 C3 C4 118.13(16) . . ?
C2 C3 H1 119.6(11) . . ?
C4 C3 H1 122.2(11) . . ?
C5 C4 C3 121.88(16) . . ?
C5 C4 N2 119.84(13) . . ?
C3 C4 N2 118.27(15) . . ?
C4 C5 C6 119.26(14) . . ?
C4 C5 H2 120.1(11) . . ?
C6 C5 H2 120.6(11) . . ?
C5 C6 C1 121.22(16) . . ?
C5 C6 H3 118.6(11) . . ?
C1 C6 H3 120.1(11) . . ?
O1 C7 H6 111.8(14) . . ?
O1 C7 H5 105.5(12) . . ?
H6 C7 H5 113(2) . . ?
O1 C7 H4 112.0(14) . . ?
H6 C7 H4 104.6(19) . . ?
H5 C7 H4 110.2(18) . . ?
O3 N1 O2 123.05(14) . . ?
O3 N1 C2 118.21(14) . . ?
O2 N1 C2 118.70(15) . . ?
O4 N2 O5 122.86(16) . . ?
O4 N2 C4 118.72(13) . . ?
O5 N2 C4 118.42(16) . . ?
C1 O1 C7 119.18(13) . . ?

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 179.39(15) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
O1 C1 C2 N1 -0.5(2) . . . . ?
C6 C1 C2 N1 -179.32(15) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
N1 C2 C3 C4 179.81(14) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C2 C3 C4 N2 -179.39(15) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
N2 C4 C5 C6 179.32(16) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
O1 C1 C6 C5 -179.39(16) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C3 C2 N1 O3 -20.5(2) . . . . ?
C1 C2 N1 O3 159.38(18) . . . . ?
C3 C2 N1 O2 157.47(17) . . . . ?
C1 C2 N1 O2 -22.7(3) . . . . ?
C5 C4 N2 O4 173.23(17) . . . . ?
C3 C4 N2 O4 -7.8(3) . . . . ?
C5 C4 N2 O5 -6.7(3) . . . . ?
C3 C4 N2 O5 172.28(16) . . . . ?
C6 C1 O1 C7 -0.5(3) . . . . ?
C2 C1 O1 C7 -179.31(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C3 H1 O4 0.92(2) 2.57(2) 3.335(3) 141.3(16) 3_565 yes
C5 H2 O2 0.983(19) 2.447(19) 3.423(3) 172.1(15) 4_455 yes
C7 H4 O5 0.95(3) 2.52(2) 3.346(3) 145.3(19) 2_545 yes
C7 H5 O2 0.92(2) 2.56(2) 3.327(3) 141.1(17) 3_755 yes

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.042
_chemical_absolute_configuration ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24dnan_208K
_database_code_depnum_ccdc_archive 'CCDC 1041035'
_audit_update_record             
;
2014-12-26 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   3.880(2)
_cell_length_b                   13.786(7)
_cell_length_c                   15.404(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.639(7)
_cell_angle_gamma                90.00
_cell_volume                     820.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    208(2)
_cell_measurement_reflns_used    2251
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9726
_exptl_absorpt_correction_T_max  0.9726
_exptl_absorpt_process_details   
;CrystalClear (Rigaku Americas and Rigaku, 2009)  
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      208(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+
;
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3737
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1847
_reflns_number_gt                1240
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Yadokari-XG 2009 (Kabuto, 2009), ORTEP-3 (Farrugia, 1997) & Mercury (Macrae et
al., 2006)
;

_computing_publication_material  
'PLATON (Speak, 2009) and publCIF (Westrip, 2010)'
_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0694P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1847
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1172
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_restrained_S_all      0.913
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1015(4) 0.18397(10) 0.92650(9) 0.0318(4) Uani 1 1 d . . .
C2 C -0.0203(4) 0.25794(10) 0.98832(9) 0.0312(4) Uani 1 1 d . . .
C3 C 0.1112(4) 0.34600(11) 0.96516(10) 0.0339(4) Uani 1 1 d . . .
H1 H 0.154(4) 0.3938(14) 1.0077(13) 0.055(5) Uiso 1 1 d . . .
C4 C 0.1603(4) 0.36133(10) 0.87855(10) 0.0337(4) Uani 1 1 d . . .
C5 C 0.0860(4) 0.29095(12) 0.81586(11) 0.0384(4) Uani 1 1 d . . .
H2 H 0.117(5) 0.3026(13) 0.7562(13) 0.050(5) Uiso 1 1 d . . .
C6 C -0.0440(4) 0.20288(12) 0.83955(10) 0.0370(4) Uani 1 1 d . . .
H3 H -0.093(4) 0.1551(11) 0.7949(11) 0.042(5) Uiso 1 1 d . . .
C7 C -0.3052(6) 0.02371(13) 0.89037(13) 0.0448(4) Uani 1 1 d . . .
H6 H -0.475(5) 0.0463(12) 0.8445(13) 0.052(5) Uiso 1 1 d . . .
H5 H -0.390(5) -0.0272(14) 0.9221(12) 0.050(5) Uiso 1 1 d . . .
H4 H -0.103(5) 0.0037(12) 0.8645(12) 0.049(5) Uiso 1 1 d . . .
N1 N -0.0672(4) 0.24486(10) 1.08114(8) 0.0400(4) Uani 1 1 d . . .
N2 N 0.3017(4) 0.45452(11) 0.85407(9) 0.0443(4) Uani 1 1 d . . .
O1 O -0.2261(3) 0.09937(8) 0.95334(7) 0.0409(3) Uani 1 1 d . . .
O2 O -0.2729(4) 0.18488(10) 1.10134(9) 0.0710(5) Uani 1 1 d . . .
O3 O 0.0947(4) 0.29657(11) 1.13349(8) 0.0751(5) Uani 1 1 d . . .
O4 O 0.3839(4) 0.46408(10) 0.78009(8) 0.0671(4) Uani 1 1 d . . .
O5 O 0.3325(5) 0.51895(10) 0.90857(9) 0.0738(5) 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
C1 O1 1.3434(18) . ?
C1 C6 1.404(2) . ?
C1 C2 1.410(2) . ?
C2 C3 1.377(2) . ?
C2 N1 1.470(2) . ?
C3 C4 1.382(2) . ?
C3 H1 0.93(2) . ?
C4 C5 1.379(2) . ?
C4 N2 1.461(2) . ?
C5 C6 1.378(2) . ?
C5 H2 0.952(19) . ?
C6 H3 0.958(17) . ?
C7 O1 1.437(2) . ?
C7 H6 0.97(2) . ?
C7 H5 0.93(2) . ?
C7 H4 0.954(19) . ?
N1 O3 1.2057(18) . ?
N1 O2 1.2108(18) . ?
N2 O5 1.2199(19) . ?
N2 O4 1.2204(17) . ?

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 C6 123.42(14) . . ?
O1 C1 C2 118.91(13) . . ?
C6 C1 C2 117.67(14) . . ?
C3 C2 C1 121.77(14) . . ?
C3 C2 N1 116.39(13) . . ?
C1 C2 N1 121.84(13) . . ?
C2 C3 C4 118.32(15) . . ?
C2 C3 H1 119.0(11) . . ?
C4 C3 H1 122.6(11) . . ?
C5 C4 C3 121.94(15) . . ?
C5 C4 N2 119.72(14) . . ?
C3 C4 N2 118.33(14) . . ?
C6 C5 C4 119.43(15) . . ?
C6 C5 H2 119.3(11) . . ?
C4 C5 H2 121.3(11) . . ?
C5 C6 C1 120.86(15) . . ?
C5 C6 H3 118.0(9) . . ?
C1 C6 H3 121.2(10) . . ?
O1 C7 H6 110.1(10) . . ?
O1 C7 H5 104.8(11) . . ?
H6 C7 H5 111.9(16) . . ?
O1 C7 H4 111.2(11) . . ?
H6 C7 H4 108.5(15) . . ?
H5 C7 H4 110.3(15) . . ?
O3 N1 O2 123.04(14) . . ?
O3 N1 C2 118.15(14) . . ?
O2 N1 C2 118.78(13) . . ?
O5 N2 O4 123.17(15) . . ?
O5 N2 C4 118.45(14) . . ?
O4 N2 C4 118.38(15) . . ?
C1 O1 C7 118.80(13) . . ?

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 179.42(13) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
O1 C1 C2 N1 0.2(2) . . . . ?
C6 C1 C2 N1 -179.26(14) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
N1 C2 C3 C4 179.85(13) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C2 C3 C4 N2 -179.64(13) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
N2 C4 C5 C6 179.35(14) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
O1 C1 C6 C5 -179.68(14) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
C3 C2 N1 O3 -20.6(2) . . . . ?
C1 C2 N1 O3 158.70(16) . . . . ?
C3 C2 N1 O2 157.37(14) . . . . ?
C1 C2 N1 O2 -23.4(2) . . . . ?
C5 C4 N2 O5 172.71(15) . . . . ?
C3 C4 N2 O5 -8.5(2) . . . . ?
C5 C4 N2 O4 -7.4(2) . . . . ?
C3 C4 N2 O4 171.38(14) . . . . ?
C6 C1 O1 C7 0.1(2) . . . . ?
C2 C1 O1 C7 -179.33(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C3 H1 O5 0.93(2) 2.564(18) 3.329(3) 139.5(13) 3_667 yes
C5 H2 O2 0.95(2) 2.47(2) 3.418(3) 173.7(15) 4_554 yes
C7 H4 O4 0.955(19) 2.521(19) 3.330(3) 142.5(15) 2_546 yes
C7 H5 O2 0.934(19) 2.54(2) 3.318(3) 140.4(15) 3_457 yes

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.041
_chemical_absolute_configuration ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24dnan_198K
_database_code_depnum_ccdc_archive 'CCDC 1041036'
_audit_update_record             
;
2014-12-26 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   3.8760(18)
_cell_length_b                   13.791(6)
_cell_length_c                   15.388(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.882(6)
_cell_angle_gamma                90.00
_cell_volume                     818.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    198
_cell_measurement_reflns_used    2246
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_min  0.9726
_exptl_absorpt_correction_T_max  0.9726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;CrystalClear (Rigaku Americas and Rigaku, 2009)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      198(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+
;
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3987
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         27.51
_reflns_number_total             1850
_reflns_number_gt                1207
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Yadokari-XG 2009 (Kabuto, 2009), ORTEP-3 (Farrugia, 1997) & Mercury (Macrae et
al., 2006)
;

_computing_publication_material  
'PLATON (Speak, 2009) and publCIF (Westrip, 2010)'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0577P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1850
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_restrained_S_all      0.916
_refine_ls_shift/su_max          0.001
_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 -0.1015(4) 0.18377(10) 0.92650(8) 0.0304(3) Uani 1 1 d . . .
C2 C -0.0200(4) 0.25774(10) 0.98827(8) 0.0300(3) Uani 1 1 d . . .
C3 C 0.1104(4) 0.34596(11) 0.96522(9) 0.0322(3) Uani 1 1 d . . .
H1 H 0.162(4) 0.3942(13) 1.0076(11) 0.044(4) Uiso 1 1 d . . .
C4 C 0.1606(4) 0.36119(10) 0.87870(9) 0.0325(4) Uani 1 1 d . . .
C5 C 0.0877(4) 0.29052(12) 0.81603(9) 0.0367(4) Uani 1 1 d . . .
H2 H 0.119(4) 0.3018(12) 0.7590(11) 0.047(5) Uiso 1 1 d . . .
C6 C -0.0419(4) 0.20249(12) 0.83989(9) 0.0353(4) Uani 1 1 d . . .
H3 H -0.089(4) 0.1544(12) 0.7952(11) 0.046(5) Uiso 1 1 d . . .
C7 C -0.3031(5) 0.02345(13) 0.89042(12) 0.0437(4) Uani 1 1 d . . .
H6 H -0.463(4) 0.0449(11) 0.8435(11) 0.044(4) Uiso 1 1 d . . .
H5 H -0.385(5) -0.0276(14) 0.9220(12) 0.058(5) Uiso 1 1 d . . .
H4 H -0.098(5) 0.0028(11) 0.8650(11) 0.048(5) Uiso 1 1 d . . .
N1 N -0.0679(4) 0.24521(10) 1.08115(7) 0.0384(3) Uani 1 1 d . . .
N2 N 0.3020(3) 0.45438(10) 0.85427(8) 0.0423(4) Uani 1 1 d . . .
O1 O -0.2250(3) 0.09920(8) 0.95350(6) 0.0386(3) Uani 1 1 d . . .
O2 O -0.2744(4) 0.18490(9) 1.10135(8) 0.0665(4) Uani 1 1 d . . .
O3 O 0.0953(4) 0.29664(10) 1.13368(7) 0.0702(5) Uani 1 1 d . . .
O4 O 0.3310(4) 0.51906(9) 0.90862(8) 0.0699(4) Uani 1 1 d . . .
O5 O 0.3862(4) 0.46368(10) 0.78033(7) 0.0638(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
C1 O1 1.3429(18) . ?
C1 C6 1.400(2) . ?
C1 C2 1.4080(19) . ?
C2 C3 1.378(2) . ?
C2 N1 1.4702(18) . ?
C3 C4 1.381(2) . ?
C3 H1 0.939(17) . ?
C4 C5 1.380(2) . ?
C4 N2 1.462(2) . ?
C5 C6 1.378(2) . ?
C5 H2 0.911(17) . ?
C6 H3 0.959(17) . ?
C7 O1 1.437(2) . ?
C7 H6 0.949(16) . ?
C7 H5 0.93(2) . ?
C7 H4 0.963(19) . ?
N1 O3 1.2050(16) . ?
N1 O2 1.2166(17) . ?
N2 O4 1.2199(18) . ?
N2 O5 1.2222(16) . ?

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 C6 123.62(13) . . ?
O1 C1 C2 118.87(12) . . ?
C6 C1 C2 117.50(13) . . ?
C3 C2 C1 121.93(13) . . ?
C3 C2 N1 116.12(12) . . ?
C1 C2 N1 121.95(13) . . ?
C2 C3 C4 118.29(14) . . ?
C2 C3 H1 120.3(10) . . ?
C4 C3 H1 121.4(10) . . ?
C5 C4 C3 121.84(14) . . ?
C5 C4 N2 119.78(13) . . ?
C3 C4 N2 118.37(14) . . ?
C6 C5 C4 119.35(14) . . ?
C6 C5 H2 119.7(11) . . ?
C4 C5 H2 120.9(11) . . ?
C5 C6 C1 121.09(14) . . ?
C5 C6 H3 117.8(10) . . ?
C1 C6 H3 121.1(10) . . ?
O1 C7 H6 111.3(10) . . ?
O1 C7 H5 104.9(11) . . ?
H6 C7 H5 113.7(15) . . ?
O1 C7 H4 111.4(10) . . ?
H6 C7 H4 106.5(14) . . ?
H5 C7 H4 109.1(15) . . ?
O3 N1 O2 123.02(13) . . ?
O3 N1 C2 118.23(13) . . ?
O2 N1 C2 118.73(13) . . ?
O4 N2 O5 123.15(15) . . ?
O4 N2 C4 118.51(13) . . ?
O5 N2 C4 118.34(14) . . ?
C1 O1 C7 118.66(12) . . ?

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 179.44(13) . . . . ?
C6 C1 C2 C3 0.6(2) . . . . ?
O1 C1 C2 N1 -0.3(2) . . . . ?
C6 C1 C2 N1 -179.15(13) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
N1 C2 C3 C4 179.91(12) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C2 C3 C4 N2 -179.43(12) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
N2 C4 C5 C6 179.28(14) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
O1 C1 C6 C5 -179.52(14) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C3 C2 N1 O3 -21.4(2) . . . . ?
C1 C2 N1 O3 158.40(15) . . . . ?
C3 C2 N1 O2 157.28(14) . . . . ?
C1 C2 N1 O2 -22.9(2) . . . . ?
C5 C4 N2 O4 172.61(15) . . . . ?
C3 C4 N2 O4 -8.7(2) . . . . ?
C5 C4 N2 O5 -7.5(2) . . . . ?
C3 C4 N2 O5 171.15(13) . . . . ?
C6 C1 O1 C7 -0.4(2) . . . . ?
C2 C1 O1 C7 -179.12(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C3 H1 O4 0.939(18) 2.537(17) 3.326(3) 141.8(13) 3_667 yes
C5 H2 O2 0.912(17) 2.509(17) 3.417(2) 174.1(14) 4_554 yes
C7 H4 O5 0.964(19) 2.518(17) 3.326(3) 141.3(14) 2_546 yes
C7 H5 O2 0.930(19) 2.546(19) 3.316(3) 140.5(15) 3_457 yes

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.040
_chemical_absolute_configuration ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24dnan_173K
_database_code_depnum_ccdc_archive 'CCDC 1041037'
_audit_update_record             
;
2014-12-26 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   3.8537(15)
_cell_length_b                   13.804(5)
_cell_length_c                   15.381(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.164(6)
_cell_angle_gamma                90.00
_cell_volume                     813.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2183
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;CrystalClear (Rigaku Americas and Rigaku, 2009)
;
_exptl_absorpt_correction_T_min  0.9724
_exptl_absorpt_correction_T_max  0.9724

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+
;
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3706
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1835
_reflns_number_gt                1372
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Yadokari-XG 2009 (Kabuto, 2009), ORTEP-3 (Farrugia, 1997) & Mercury (Macrae et
al., 2006)
;

_computing_publication_material  
'PLATON (Speak, 2009) and publCIF (Westrip, 2010)'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0684P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1835
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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 0.4002(4) 0.18302(10) 0.92685(9) 0.0254(3) Uani 1 1 d . . .
C2 C 0.4802(4) 0.25744(10) 0.98871(9) 0.0257(3) Uani 1 1 d . . .
C3 C 0.6106(4) 0.34586(11) 0.96564(9) 0.0271(3) Uani 1 1 d . . .
H1 H 0.657(4) 0.3939(14) 1.0081(12) 0.041(5) Uiso 1 1 d . . .
C4 C 0.6625(4) 0.36070(10) 0.87894(9) 0.0276(3) Uani 1 1 d . . .
C5 C 0.5913(4) 0.28956(12) 0.81616(9) 0.0304(4) Uani 1 1 d . . .
H2 H 0.621(5) 0.3010(13) 0.7571(12) 0.040(5) Uiso 1 1 d . . .
C6 C 0.4617(4) 0.20155(11) 0.84008(9) 0.0291(3) Uani 1 1 d . . .
H3 H 0.414(5) 0.1539(12) 0.7942(12) 0.037(5) Uiso 1 1 d . . .
C7 C 0.2001(5) 0.02270(12) 0.89040(11) 0.0358(4) Uani 1 1 d . . .
H6 H 0.036(5) 0.0459(12) 0.8425(12) 0.041(5) Uiso 1 1 d . . .
H5 H 0.109(5) -0.0294(14) 0.9215(12) 0.048(5) Uiso 1 1 d . . .
H4 H 0.410(5) 0.0007(11) 0.8658(11) 0.034(4) Uiso 1 1 d . . .
N1 N 0.4314(4) 0.24501(9) 1.08162(8) 0.0314(3) Uani 1 1 d . . .
N2 N 0.8021(4) 0.45417(10) 0.85462(8) 0.0348(3) Uani 1 1 d . . .
O1 O 0.2765(3) 0.09857(8) 0.95368(6) 0.0319(3) Uani 1 1 d . . .
O2 O 0.2238(4) 0.18444(9) 1.10154(8) 0.0537(4) Uani 1 1 d . . .
O3 O 0.5977(4) 0.29676(10) 1.13437(7) 0.0564(4) Uani 1 1 d . . .
O4 O 0.8245(4) 0.51938(9) 0.90873(8) 0.0572(4) Uani 1 1 d . . .
O5 O 0.8920(4) 0.46274(10) 0.78091(8) 0.0527(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
C1 O1 1.3412(18) . ?
C1 C6 1.404(2) . ?
C1 C2 1.412(2) . ?
C2 C3 1.381(2) . ?
C2 N1 1.4714(18) . ?
C3 C4 1.385(2) . ?
C3 H1 0.934(19) . ?
C4 C5 1.384(2) . ?
C4 N2 1.462(2) . ?
C5 C6 1.378(2) . ?
C5 H2 0.941(18) . ?
C6 H3 0.967(17) . ?
C7 O1 1.4384(19) . ?
C7 H6 0.971(19) . ?
C7 H5 0.95(2) . ?
C7 H4 0.978(18) . ?
N1 O3 1.2115(17) . ?
N1 O2 1.2188(17) . ?
N2 O4 1.2227(18) . ?
N2 O5 1.2263(16) . ?

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 C6 123.56(13) . . ?
O1 C1 C2 118.97(12) . . ?
C6 C1 C2 117.47(13) . . ?
C3 C2 C1 121.96(13) . . ?
C3 C2 N1 116.15(12) . . ?
C1 C2 N1 121.89(13) . . ?
C2 C3 C4 118.19(14) . . ?
C2 C3 H1 119.7(11) . . ?
C4 C3 H1 122.1(11) . . ?
C5 C4 C3 121.92(14) . . ?
C5 C4 N2 119.90(13) . . ?
C3 C4 N2 118.18(13) . . ?
C6 C5 C4 119.31(14) . . ?
C6 C5 H2 119.4(11) . . ?
C4 C5 H2 121.3(11) . . ?
C5 C6 C1 121.15(14) . . ?
C5 C6 H3 116.8(10) . . ?
C1 C6 H3 122.1(10) . . ?
O1 C7 H6 110.0(10) . . ?
O1 C7 H5 105.7(11) . . ?
H6 C7 H5 112.7(15) . . ?
O1 C7 H4 111.7(10) . . ?
H6 C7 H4 107.8(14) . . ?
H5 C7 H4 108.9(14) . . ?
O3 N1 O2 123.40(13) . . ?
O3 N1 C2 117.90(13) . . ?
O2 N1 C2 118.69(13) . . ?
O4 N2 O5 123.51(14) . . ?
O4 N2 C4 118.45(12) . . ?
O5 N2 C4 118.04(14) . . ?
C1 O1 C7 118.57(12) . . ?

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 179.55(13) . . . . ?
C6 C1 C2 C3 0.7(2) . . . . ?
O1 C1 C2 N1 -0.1(2) . . . . ?
C6 C1 C2 N1 -178.94(13) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
N1 C2 C3 C4 179.70(12) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C2 C3 C4 N2 -179.72(13) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
N2 C4 C5 C6 179.61(14) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
O1 C1 C6 C5 -179.59(14) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C3 C2 N1 O3 -21.8(2) . . . . ?
C1 C2 N1 O3 157.80(15) . . . . ?
C3 C2 N1 O2 157.28(14) . . . . ?
C1 C2 N1 O2 -23.1(2) . . . . ?
C5 C4 N2 O4 171.66(14) . . . . ?
C3 C4 N2 O4 -9.4(2) . . . . ?
C5 C4 N2 O5 -8.6(2) . . . . ?
C3 C4 N2 O5 170.33(14) . . . . ?
C6 C1 O1 C7 -0.4(2) . . . . ?
C2 C1 O1 C7 -179.19(14) . . . . ?


loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C3 H1 O4 0.934(19) 2.552(17) 3.321(2) 139.8(13) 3_767 yes
C5 H2 O2 0.941(19) 2.475(18) 3.413(2) 174.6(15) 4_554 yes
C7 H4 O5 0.978(19) 2.514(17) 3.315(3) 139.1(14) 2_646 yes
C7 H5 O2 0.952(19) 2.501(19) 3.302(3) 141.9(15) 3_557 yes

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.045
_chemical_absolute_configuration ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24dnan_128K
_database_code_depnum_ccdc_archive 'CCDC 1041038'
_audit_update_record             
;
2014-12-26 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   3.8278(18)
_cell_length_b                   13.813(6)
_cell_length_c                   15.364(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.512(7)
_cell_angle_gamma                90.00
_cell_volume                     807.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    128
_cell_measurement_reflns_used    2454
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9722
_exptl_absorpt_correction_T_max  0.9722
_exptl_absorpt_process_details   
;CrystalClear (Rigaku Americas and Rigaku, 2009)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      128(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+
;
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3639
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1814
_reflns_number_gt                1364
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Yadokari-XG 2009 (Kabuto, 2009), ORTEP-3 (Farrugia, 1997) & Mercury (Macrae et
al., 2006)
;

_computing_publication_material  
'PLATON (Speak, 2009) and publCIF (Westrip, 2010)'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0523P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1814
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0856
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_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 0.5971(3) 0.18249(8) 0.07287(8) 0.0201(3) Uani 1 1 d . . .
C2 C 0.5186(3) 0.25714(9) 0.01077(8) 0.0200(3) Uani 1 1 d . . .
C3 C 0.3884(3) 0.34540(9) 0.03397(8) 0.0219(3) Uani 1 1 d . . .
H1 H 0.343(4) 0.3937(11) -0.0079(10) 0.031(4) Uiso 1 1 d . . .
C4 C 0.3356(3) 0.36030(8) 0.12049(8) 0.0216(3) Uani 1 1 d . . .
C5 C 0.4049(3) 0.28894(9) 0.18353(8) 0.0238(3) Uani 1 1 d . . .
H2 H 0.374(4) 0.3013(11) 0.2426(11) 0.036(4) Uiso 1 1 d . . .
C6 C 0.5340(3) 0.20073(9) 0.15963(9) 0.0234(3) Uani 1 1 d . . .
H3 H 0.576(4) 0.1526(9) 0.2031(10) 0.026(4) Uiso 1 1 d . . .
C7 C 0.7964(4) 0.02188(10) 0.10966(9) 0.0275(3) Uani 1 1 d . . .
H6 H 0.967(4) 0.0431(9) 0.1575(9) 0.023(3) Uiso 1 1 d . . .
H5 H 0.896(4) -0.0302(11) 0.0781(10) 0.032(4) Uiso 1 1 d . . .
H4 H 0.586(4) 0.0004(9) 0.1321(9) 0.026(4) Uiso 1 1 d . . .
N1 N 0.5677(3) 0.24492(8) -0.08225(7) 0.0241(3) Uani 1 1 d . . .
N2 N 0.1972(3) 0.45384(8) 0.14508(7) 0.0271(3) Uani 1 1 d . . .
O1 O 0.7208(2) 0.09798(6) 0.04604(6) 0.0251(2) Uani 1 1 d . . .
O2 O 0.7771(3) 0.18406(7) -0.10195(7) 0.0391(3) Uani 1 1 d . . .
O3 O 0.3997(3) 0.29714(7) -0.13518(6) 0.0415(3) Uani 1 1 d . . .
O4 O 0.1812(3) 0.51952(7) 0.09122(7) 0.0427(3) Uani 1 1 d . . .
O5 O 0.1012(3) 0.46205(7) 0.21842(6) 0.0394(3) 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
C1 O1 1.3421(15) . ?
C1 C6 1.4041(18) . ?
C1 C2 1.4138(18) . ?
C2 C3 1.3791(19) . ?
C2 N1 1.4721(17) . ?
C3 C4 1.3825(18) . ?
C3 H1 0.929(15) . ?
C4 C5 1.3863(18) . ?
C4 N2 1.4623(17) . ?
C5 C6 1.380(2) . ?
C5 H2 0.944(16) . ?
C6 H3 0.944(14) . ?
C7 O1 1.4423(16) . ?
C7 H6 0.972(15) . ?
C7 H5 0.969(16) . ?
C7 H4 0.958(14) . ?
N1 O3 1.2149(14) . ?
N1 O2 1.2233(15) . ?
N2 O4 1.2248(15) . ?
N2 O5 1.2295(14) . ?

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 C6 123.53(11) . . ?
O1 C1 C2 118.84(11) . . ?
C6 C1 C2 117.62(11) . . ?
C3 C2 C1 121.71(12) . . ?
C3 C2 N1 116.22(11) . . ?
C1 C2 N1 122.07(11) . . ?
C2 C3 C4 118.47(12) . . ?
C2 C3 H1 120.1(9) . . ?
C4 C3 H1 121.4(9) . . ?
C3 C4 C5 121.92(12) . . ?
C3 C4 N2 118.48(11) . . ?
C5 C4 N2 119.60(11) . . ?
C6 C5 C4 119.19(12) . . ?
C6 C5 H2 120.2(9) . . ?
C4 C5 H2 120.6(9) . . ?
C5 C6 C1 121.08(12) . . ?
C5 C6 H3 118.2(8) . . ?
C1 C6 H3 120.8(8) . . ?
O1 C7 H6 111.0(8) . . ?
O1 C7 H5 105.2(8) . . ?
H6 C7 H5 109.5(12) . . ?
O1 C7 H4 110.9(9) . . ?
H6 C7 H4 110.0(12) . . ?
H5 C7 H4 110.1(11) . . ?
O3 N1 O2 123.67(11) . . ?
O3 N1 C2 117.75(11) . . ?
O2 N1 C2 118.57(10) . . ?
O4 N2 O5 123.61(11) . . ?
O4 N2 C4 118.15(11) . . ?
O5 N2 C4 118.23(11) . . ?
C1 O1 C7 118.45(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.53(11) . . . . ?
C6 C1 C2 C3 0.73(19) . . . . ?
O1 C1 C2 N1 0.13(18) . . . . ?
C6 C1 C2 N1 -178.67(11) . . . . ?
C1 C2 C3 C4 0.18(19) . . . . ?
N1 C2 C3 C4 179.61(11) . . . . ?
C2 C3 C4 C5 -0.93(19) . . . . ?
C2 C3 C4 N2 -179.93(11) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
N2 C4 C5 C6 179.72(11) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
O1 C1 C6 C5 -179.68(12) . . . . ?
C2 C1 C6 C5 -0.94(19) . . . . ?
C3 C2 N1 O3 -21.84(17) . . . . ?
C1 C2 N1 O3 157.58(12) . . . . ?
C3 C2 N1 O2 157.22(12) . . . . ?
C1 C2 N1 O2 -23.35(18) . . . . ?
C3 C4 N2 O4 -10.23(18) . . . . ?
C5 C4 N2 O4 170.74(12) . . . . ?
C3 C4 N2 O5 169.30(11) . . . . ?
C5 C4 N2 O5 -9.73(18) . . . . ?
C6 C1 O1 C7 -0.58(18) . . . . ?
C2 C1 O1 C7 -179.30(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C3 H1 O4 0.929(15) 2.553(15) 3.314(2) 139.4(12) 3_565 yes
C5 H2 O2 0.944(17) 2.467(17) 3.407(2) 174.1(13) 4_455 yes
C7 H4 O5 0.958(15) 2.538(14) 3.300(2) 136.5(11) 2_545 yes
C7 H5 O2 0.970(15) 2.472(15) 3.289(2) 141.7(12) 3_755 yes

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.044
_chemical_absolute_configuration ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24dnan_100K
_database_code_depnum_ccdc_archive 'CCDC 1041039'
_audit_update_record             
;
2014-12-26 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   3.8139(10)
_cell_length_b                   13.823(4)
_cell_length_c                   15.349(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.777(4)
_cell_angle_gamma                90.00
_cell_volume                     803.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2285
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5


_exptl_crystal_description       Platelet
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9721
_exptl_absorpt_correction_T_max  0.9721
_exptl_absorpt_process_details   
;CrystalClear (Rigaku Americas and Rigaku, 2009)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+
;
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4126
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1812
_reflns_number_gt                1496
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Yadokari-XG 2009 (Kabuto, 2009), ORTEP-3 (Farrugia, 1997) & Mercury (Macrae et
al., 2006)
;

_computing_publication_material  
'PLATON (Speak, 2009) and publCIF (Westrip, 2010)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0578P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1812
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.5950(3) 0.81802(8) 0.07270(8) 0.0166(3) Uani 1 1 d . . .
C2 C 0.5176(3) 0.74324(8) 0.01057(8) 0.0168(3) Uani 1 1 d . . .
C3 C 0.3874(3) 0.65451(8) 0.03362(8) 0.0179(3) Uani 1 1 d . . .
H1 H 0.338(4) 0.6073(11) -0.0083(10) 0.029(4) Uiso 1 1 d . . .
C4 C 0.3343(3) 0.64012(8) 0.12034(8) 0.0176(3) Uani 1 1 d . . .
C5 C 0.4019(3) 0.71156(9) 0.18341(8) 0.0191(3) Uani 1 1 d . . .
H2 H 0.374(4) 0.6985(11) 0.2435(11) 0.031(4) Uiso 1 1 d . . .
C6 C 0.5313(3) 0.79991(8) 0.15952(8) 0.0182(3) Uani 1 1 d . . .
H3 H 0.575(4) 0.8481(10) 0.2039(10) 0.025(4) Uiso 1 1 d . . .
C7 C 0.7946(3) 0.97855(9) 0.10986(9) 0.0216(3) Uani 1 1 d . . .
H6 H 0.964(4) 0.9573(9) 0.1596(9) 0.020(3) Uiso 1 1 d . . .
H5 H 0.891(4) 1.0285(11) 0.0792(10) 0.030(4) Uiso 1 1 d . . .
H4 H 0.581(4) 1.0023(9) 0.1324(9) 0.024(3) Uiso 1 1 d . . .
N1 N 0.5663(3) 0.75517(7) -0.08261(7) 0.0190(2) Uani 1 1 d . . .
N2 N 0.1966(3) 0.54621(7) 0.14478(7) 0.0213(2) Uani 1 1 d . . .
O1 O 0.7198(2) 0.90250(6) 0.04585(5) 0.0200(2) Uani 1 1 d . . .
O2 O 0.7774(3) 0.81617(6) -0.10222(6) 0.0301(3) Uani 1 1 d . . .
O3 O 0.3973(3) 0.70266(7) -0.13575(6) 0.0319(3) Uani 1 1 d . . .
O4 O 0.1845(3) 0.48012(7) 0.09116(6) 0.0327(3) Uani 1 1 d . . .
O5 O 0.0971(3) 0.53835(7) 0.21799(6) 0.0304(2) 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
C1 O1 1.3440(14) . ?
C1 C6 1.4050(16) . ?
C1 C2 1.4138(16) . ?
C2 C3 1.3846(16) . ?
C2 N1 1.4731(15) . ?
C3 C4 1.3842(16) . ?
C3 H1 0.920(16) . ?
C4 C5 1.3856(17) . ?
C4 N2 1.4657(15) . ?
C5 C6 1.3829(17) . ?
C5 H2 0.958(16) . ?
C6 H3 0.953(15) . ?
C7 O1 1.4442(15) . ?
C7 H6 0.986(14) . ?
C7 H5 0.936(16) . ?
C7 H4 0.977(14) . ?
N1 O3 1.2180(13) . ?
N1 O2 1.2276(13) . ?
N2 O4 1.2269(13) . ?
N2 O5 1.2325(13) . ?

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 C6 123.56(10) . . ?
O1 C1 C2 118.80(10) . . ?
C6 C1 C2 117.63(10) . . ?
C3 C2 C1 121.87(11) . . ?
C3 C2 N1 115.94(10) . . ?
C1 C2 N1 122.19(10) . . ?
C4 C3 C2 118.07(11) . . ?
C4 C3 H1 122.0(9) . . ?
C2 C3 H1 119.9(9) . . ?
C3 C4 C5 122.22(11) . . ?
C3 C4 N2 118.10(10) . . ?
C5 C4 N2 119.67(10) . . ?
C6 C5 C4 119.14(11) . . ?
C6 C5 H2 120.4(9) . . ?
C4 C5 H2 120.3(9) . . ?
C5 C6 C1 121.06(11) . . ?
C5 C6 H3 117.7(8) . . ?
C1 C6 H3 121.2(8) . . ?
O1 C7 H6 111.7(7) . . ?
O1 C7 H5 104.6(9) . . ?
H6 C7 H5 110.3(12) . . ?
O1 C7 H4 112.3(8) . . ?
H6 C7 H4 108.9(11) . . ?
H5 C7 H4 109.0(12) . . ?
O3 N1 O2 123.77(10) . . ?
O3 N1 C2 117.77(9) . . ?
O2 N1 C2 118.45(10) . . ?
O4 N2 O5 123.70(10) . . ?
O4 N2 C4 118.29(10) . . ?
O5 N2 C4 118.01(10) . . ?
C1 O1 C7 118.20(9) . . ?

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 -179.82(10) . . . . ?
C6 C1 C2 C3 -0.75(17) . . . . ?
O1 C1 C2 N1 -0.52(16) . . . . ?
C6 C1 C2 N1 178.55(10) . . . . ?
C1 C2 C3 C4 -0.13(17) . . . . ?
N1 C2 C3 C4 -179.47(10) . . . . ?
C2 C3 C4 C5 0.98(17) . . . . ?
C2 C3 C4 N2 -179.99(9) . . . . ?
C3 C4 C5 C6 -0.90(18) . . . . ?
N2 C4 C5 C6 -179.91(10) . . . . ?
C4 C5 C6 C1 -0.05(18) . . . . ?
O1 C1 C6 C5 179.85(10) . . . . ?
C2 C1 C6 C5 0.84(17) . . . . ?
C3 C2 N1 O3 21.98(15) . . . . ?
C1 C2 N1 O3 -157.36(11) . . . . ?
C3 C2 N1 O2 -157.03(10) . . . . ?
C1 C2 N1 O2 23.63(16) . . . . ?
C3 C4 N2 O4 10.74(16) . . . . ?
C5 C4 N2 O4 -170.22(11) . . . . ?
C3 C4 N2 O5 -168.77(10) . . . . ?
C5 C4 N2 O5 10.28(16) . . . . ?
C6 C1 O1 C7 0.42(16) . . . . ?
C2 C1 O1 C7 179.43(10) . . . . ?


loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C3 H1 O4 0.920(15) 2.540(15) 3.3020(18) 140.5(12) 3_565 yes
C5 H2 O2 0.958(17) 2.448(17) 3.4011(18) 173.5(13) 4_465 yes
C7 H4 O5 0.979(15) 2.520(14) 3.2907(19) 135.5(11) 2_555 yes
C7 H5 O2 0.935(15) 2.496(15) 3.2826(18) 141.9(12) 3_775 yes

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.045

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24DNAN_a_100K
_database_code_depnum_ccdc_archive 'CCDC 1401650'
_audit_update_record             
;
2015-05-18 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          369.8
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.593(2)
_cell_length_b                   12.641(3)
_cell_length_c                   15.263(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.065(4)
_cell_angle_gamma                90.00
_cell_volume                     1645.3(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4678
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.9701
_exptl_absorpt_correction_T_max  0.9794
_exptl_absorpt_process_details   
;CrystalClear (Rigaku Americas and Rigaku, 2009)
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12659
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3767
_reflns_number_gt                2565
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0325P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3767
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0729
_refine_ls_wR_factor_gt          0.0670
_refine_ls_goodness_of_fit_ref   0.879
_refine_ls_restrained_S_all      0.879
_refine_ls_shift/su_max          0.001
_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 0.30524(16) 0.42648(10) 0.47082(9) 0.0202(3) Uani 1 1 d . . .
C2 C 0.19295(16) 0.48082(10) 0.41227(9) 0.0203(3) Uani 1 1 d . . .
C3 C 0.14754(16) 0.44666(11) 0.32718(9) 0.0212(3) Uani 1 1 d . . .
H1 H 0.0692 0.4830 0.2894 0.025 Uiso 1 1 calc R . .
C4 C 0.22000(16) 0.35784(11) 0.29898(9) 0.0206(3) Uani 1 1 d . . .
C5 C 0.33015(16) 0.30187(11) 0.35399(9) 0.0221(3) Uani 1 1 d . . .
H2 H 0.3777 0.2407 0.3328 0.027 Uiso 1 1 calc R . .
C6 C 0.37097(15) 0.33503(11) 0.43987(9) 0.0217(3) Uani 1 1 d . . .
H3 H 0.4444 0.2952 0.4782 0.026 Uiso 1 1 calc R . .
C7 C 0.42456(19) 0.39626(12) 0.61755(10) 0.0340(4) Uani 1 1 d . . .
H4 H 0.3696 0.3285 0.6192 0.051 Uiso 1 1 calc R . .
H5 H 0.4317 0.4299 0.6757 0.051 Uiso 1 1 calc R . .
H6 H 0.5303 0.3841 0.6018 0.051 Uiso 1 1 calc R . .
O1 O 0.33931(11) 0.46428(7) 0.55271(6) 0.0262(2) Uani 1 1 d . . .
O2 O 0.19437(14) 0.63755(8) 0.49108(7) 0.0358(3) Uani 1 1 d . . .
O3 O -0.02037(13) 0.59112(8) 0.41038(7) 0.0391(3) Uani 1 1 d . . .
O4 O 0.07180(12) 0.36536(9) 0.16157(7) 0.0349(3) Uani 1 1 d . . .
O5 O 0.25907(13) 0.24993(9) 0.18198(7) 0.0401(3) Uani 1 1 d . . .
N1 N 0.11722(15) 0.57667(9) 0.44031(8) 0.0270(3) Uani 1 1 d . . .
N2 N 0.18031(14) 0.32187(10) 0.20797(8) 0.0271(3) Uani 1 1 d . . .
C8 C 0.21567(15) 0.07590(10) 0.63864(9) 0.0189(3) Uani 1 1 d . A .
C9 C 0.27037(16) 0.00324(11) 0.57995(9) 0.0220(3) Uani 1 1 d . . .
C10 C 0.22951(16) 0.00951(11) 0.48988(9) 0.0235(3) Uani 1 1 d . A .
H7 H 0.2687 -0.0402 0.4514 0.028 Uiso 1 1 calc R . .
C11 C 0.13070(15) 0.08949(11) 0.45724(9) 0.0189(3) Uani 1 1 d . . .
C12 C 0.07454(16) 0.16306(11) 0.51184(9) 0.0221(3) Uani 1 1 d . A .
H8 H 0.0070 0.2180 0.4877 0.027 Uiso 1 1 calc R . .
C13 C 0.11688(16) 0.15661(10) 0.60198(9) 0.0223(3) Uani 1 1 d . . .
H9 H 0.0784 0.2077 0.6396 0.027 Uiso 1 1 calc R A .
C14 C 0.21346(18) 0.14421(12) 0.78379(9) 0.0307(4) Uani 1 1 d . A .
H10 H 0.2554 0.2129 0.7683 0.046 Uiso 1 1 calc R . .
H11 H 0.2546 0.1263 0.8447 0.046 Uiso 1 1 calc R . .
H12 H 0.0988 0.1479 0.7783 0.046 Uiso 1 1 calc R . .
O6 O 0.25995(11) 0.06411(7) 0.72504(6) 0.0241(2) Uani 1 1 d . . .
O7A O 0.3886(6) -0.1106(5) 0.6859(5) 0.0316(10) Uani 0.676(3) 1 d P A 1
O7B O 0.4383(13) -0.0947(11) 0.6803(10) 0.045(3) Uani 0.324(3) 1 d P A 2
O8A O 0.4780(2) -0.10583(13) 0.55893(10) 0.0363(6) Uani 0.676(3) 1 d P A 1
O8B O 0.3369(4) -0.1781(2) 0.5669(2) 0.0353(12) Uani 0.324(3) 1 d P A 2
O9 O 0.13435(13) 0.02778(9) 0.31480(6) 0.0368(3) Uani 1 1 d . . .
O10 O -0.00460(12) 0.16683(8) 0.33345(7) 0.0307(3) Uani 1 1 d . . .
N3A N 0.3887(9) -0.0800(4) 0.6110(5) 0.0240(12) Uani 0.676(3) 1 d P A 1
N3B N 0.3490(19) -0.0889(12) 0.6118(12) 0.046(4) Uani 0.324(3) 1 d P A 2
N4 N 0.08396(13) 0.09524(9) 0.36205(8) 0.0234(3) Uani 1 1 d . A .


_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 O1 1.3365(16) . ?
C1 C6 1.3944(19) . ?
C1 C2 1.4104(18) . ?
C2 C3 1.3788(19) . ?
C2 N1 1.4640(17) . ?
C3 C4 1.3782(19) . ?
C3 H1 0.9500 . ?
C4 C5 1.3805(18) . ?
C4 N2 1.4616(18) . ?
C5 C6 1.3798(19) . ?
C5 H2 0.9500 . ?
C6 H3 0.9500 . ?
C7 O1 1.4412(16) . ?
C7 H4 0.9800 . ?
C7 H5 0.9800 . ?
C7 H6 0.9800 . ?
O2 N1 1.2272(15) . ?
O3 N1 1.2276(15) . ?
O4 N2 1.2291(15) . ?
O5 N2 1.2282(15) . ?
C8 O6 1.3351(16) . ?
C8 C13 1.3991(18) . ?
C8 C9 1.4038(19) . ?
C9 C10 1.3786(19) . ?
C9 N3B 1.404(15) . ?
C9 N3A 1.499(6) . ?
C10 C11 1.3739(19) . ?
C10 H7 0.9500 . ?
C11 C12 1.3752(19) . ?
C11 N4 1.4607(17) . ?
C12 C13 1.3816(19) . ?
C12 H8 0.9500 . ?
C13 H9 0.9500 . ?
C14 O6 1.4413(16) . ?
C14 H10 0.9800 . ?
C14 H11 0.9800 . ?
C14 H12 0.9800 . ?
O7A N3A 1.207(11) . ?
O7B N3B 1.22(2) . ?
O8A N3A 1.215(8) . ?
O8B N3B 1.317(17) . ?
O9 N4 1.2296(15) . ?
O10 N4 1.2275(14) . ?

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 C6 124.19(12) . . ?
O1 C1 C2 118.19(12) . . ?
C6 C1 C2 117.59(12) . . ?
C3 C2 C1 122.45(12) . . ?
C3 C2 N1 116.75(12) . . ?
C1 C2 N1 120.79(12) . . ?
C4 C3 C2 117.58(12) . . ?
C4 C3 H1 121.2 . . ?
C2 C3 H1 121.2 . . ?
C3 C4 C5 122.00(13) . . ?
C3 C4 N2 119.25(12) . . ?
C5 C4 N2 118.75(12) . . ?
C6 C5 C4 119.82(13) . . ?
C6 C5 H2 120.1 . . ?
C4 C5 H2 120.1 . . ?
C5 C6 C1 120.50(13) . . ?
C5 C6 H3 119.8 . . ?
C1 C6 H3 119.8 . . ?
O1 C7 H4 109.5 . . ?
O1 C7 H5 109.5 . . ?
H4 C7 H5 109.5 . . ?
O1 C7 H6 109.5 . . ?
H4 C7 H6 109.5 . . ?
H5 C7 H6 109.5 . . ?
C1 O1 C7 117.60(11) . . ?
O2 N1 O3 124.23(12) . . ?
O2 N1 C2 118.59(12) . . ?
O3 N1 C2 117.18(12) . . ?
O5 N2 O4 123.66(12) . . ?
O5 N2 C4 117.63(12) . . ?
O4 N2 C4 118.71(12) . . ?
O6 C8 C13 124.17(12) . . ?
O6 C8 C9 118.69(12) . . ?
C13 C8 C9 117.14(12) . . ?
C10 C9 N3B 116.5(8) . . ?
C10 C9 C8 122.31(12) . . ?
N3B C9 C8 120.4(8) . . ?
C10 C9 N3A 115.8(3) . . ?
N3B C9 N3A 13.8(9) . . ?
C8 C9 N3A 121.6(3) . . ?
C11 C10 C9 118.31(13) . . ?
C11 C10 H7 120.8 . . ?
C9 C10 H7 120.8 . . ?
C10 C11 C12 121.67(13) . . ?
C10 C11 N4 118.65(12) . . ?
C12 C11 N4 119.68(12) . . ?
C11 C12 C13 119.64(13) . . ?
C11 C12 H8 120.2 . . ?
C13 C12 H8 120.2 . . ?
C12 C13 C8 120.91(13) . . ?
C12 C13 H9 119.5 . . ?
C8 C13 H9 119.5 . . ?
O6 C14 H10 109.5 . . ?
O6 C14 H11 109.5 . . ?
H10 C14 H11 109.5 . . ?
O6 C14 H12 109.5 . . ?
H10 C14 H12 109.5 . . ?
H11 C14 H12 109.5 . . ?
C8 O6 C14 117.97(11) . . ?
O7A N3A O8A 127.4(6) . . ?
O7A N3A C9 116.4(6) . . ?
O8A N3A C9 116.1(5) . . ?
O7B N3B O8B 113.3(13) . . ?
O7B N3B C9 124.9(14) . . ?
O8B N3B C9 121.7(13) . . ?
O10 N4 O9 123.39(12) . . ?
O10 N4 C11 118.23(12) . . ?
O9 N4 C11 118.38(11) . . ?

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 -178.55(13) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
O1 C1 C2 N1 0.66(19) . . . . ?
C6 C1 C2 N1 179.20(12) . . . . ?
C1 C2 C3 C4 -2.1(2) . . . . ?
N1 C2 C3 C4 178.64(12) . . . . ?
C2 C3 C4 C5 2.3(2) . . . . ?
C2 C3 C4 N2 -177.25(12) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
N2 C4 C5 C6 179.21(12) . . . . ?
C4 C5 C6 C1 -1.9(2) . . . . ?
O1 C1 C6 C5 -179.51(12) . . . . ?
C2 C1 C6 C5 2.05(19) . . . . ?
C6 C1 O1 C7 -12.67(19) . . . . ?
C2 C1 O1 C7 165.77(12) . . . . ?
C3 C2 N1 O2 -145.24(13) . . . . ?
C1 C2 N1 O2 35.50(18) . . . . ?
C3 C2 N1 O3 34.14(18) . . . . ?
C1 C2 N1 O3 -145.12(13) . . . . ?
C3 C4 N2 O5 172.03(13) . . . . ?
C5 C4 N2 O5 -7.55(19) . . . . ?
C3 C4 N2 O4 -7.34(19) . . . . ?
C5 C4 N2 O4 173.09(12) . . . . ?
O6 C8 C9 C10 179.64(13) . . . . ?
C13 C8 C9 C10 -0.2(2) . . . . ?
O6 C8 C9 N3B 9.9(8) . . . . ?
C13 C8 C9 N3B -169.9(8) . . . . ?
O6 C8 C9 N3A -6.1(4) . . . . ?
C13 C8 C9 N3A 174.1(3) . . . . ?
N3B C9 C10 C11 169.5(8) . . . . ?
C8 C9 C10 C11 -0.5(2) . . . . ?
N3A C9 C10 C11 -175.1(3) . . . . ?
C9 C10 C11 C12 0.9(2) . . . . ?
C9 C10 C11 N4 -178.61(12) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
N4 C11 C12 C13 179.01(12) . . . . ?
C11 C12 C13 C8 -0.3(2) . . . . ?
O6 C8 C13 C12 -179.22(13) . . . . ?
C9 C8 C13 C12 0.63(19) . . . . ?
C13 C8 O6 C14 -5.19(19) . . . . ?
C9 C8 O6 C14 174.96(12) . . . . ?
C10 C9 N3A O7A -156.5(5) . . . . ?
N3B C9 N3A O7A -60(4) . . . . ?
C8 C9 N3A O7A 28.9(8) . . . . ?
C10 C9 N3A O8A 26.3(6) . . . . ?
N3B C9 N3A O8A 123(5) . . . . ?
C8 C9 N3A O8A -148.3(4) . . . . ?
C10 C9 N3B O7B 153.8(14) . . . . ?
C8 C9 N3B O7B -36(2) . . . . ?
N3A C9 N3B O7B 63(4) . . . . ?
C10 C9 N3B O8B -23.4(17) . . . . ?
C8 C9 N3B O8B 146.9(11) . . . . ?
N3A C9 N3B O8B -114(5) . . . . ?
C10 C11 N4 O10 179.86(12) . . . . ?
C12 C11 N4 O10 0.32(19) . . . . ?
C10 C11 N4 O9 0.38(19) . . . . ?
C12 C11 N4 O9 -179.15(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.041

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24DNAN_a_133K
_database_code_depnum_ccdc_archive 'CCDC 1401651'
_audit_update_record             
;
2015-05-18 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.608(2)
_cell_length_b                   12.658(3)
_cell_length_c                   15.282(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.022(3)
_cell_angle_gamma                90.00
_cell_volume                     1652.6(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4486
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9702
_exptl_absorpt_correction_T_max  0.9795
_exptl_absorpt_process_details   
;CrystalClear (Rigaku Americas and Rigaku, 2009)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13148
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.44
_reflns_number_total             3767
_reflns_number_gt                3002
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0495P)²+0.1403P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3767
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.0985
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.006
_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
C4 C 0.19530(16) 0.07353(11) 0.52931(9) 0.0226(3) Uani 1 1 d . . .
C10 C 0.30723(16) 0.01952(11) 0.58797(9) 0.0230(3) Uani 1 1 d . . .
C2 C 0.35247(16) 0.05356(11) 0.67301(9) 0.0236(3) Uani 1 1 d . . .
H1 H 0.4306 0.0172 0.7108 0.028 Uiso 1 1 calc R . .
C9 C 0.27997(16) 0.14254(11) 0.70114(9) 0.0230(3) Uani 1 1 d . . .
C1 C 0.16954(16) 0.19794(11) 0.64609(10) 0.0246(3) Uani 1 1 d . . .
H2 H 0.1217 0.2589 0.6673 0.030 Uiso 1 1 calc R . .
C8 C 0.12875(16) 0.16487(11) 0.56041(9) 0.0245(3) Uani 1 1 d . . .
H3 H 0.0550 0.2043 0.5222 0.029 Uiso 1 1 calc R . .
C13 C 0.0756(2) 0.10369(13) 0.38270(11) 0.0379(4) Uani 1 1 d . . .
H4 H -0.0296 0.1162 0.3988 0.057 Uiso 1 1 calc R . .
H5 H 0.0677 0.0698 0.3247 0.057 Uiso 1 1 calc R . .
H6 H 0.1307 0.1712 0.3806 0.057 Uiso 1 1 calc R . .
O4 O 0.16095(12) 0.03594(8) 0.44738(6) 0.0297(3) Uani 1 1 d . . .
O9 O 0.30649(15) -0.13696(9) 0.50907(7) 0.0401(3) Uani 1 1 d . . .
O7 O 0.51984(14) -0.09078(9) 0.58994(8) 0.0437(3) Uani 1 1 d . . .
O8 O 0.42763(13) 0.13496(10) 0.83837(7) 0.0395(3) Uani 1 1 d . . .
O5 O 0.24088(15) 0.24996(10) 0.81804(8) 0.0464(3) Uani 1 1 d . . .
N3 N 0.38321(16) -0.07611(10) 0.55983(8) 0.0299(3) Uani 1 1 d . . .
N2 N 0.31928(15) 0.17817(11) 0.79208(8) 0.0299(3) Uani 1 1 d . . .
C3 C 0.28428(16) 0.42404(11) 0.36156(9) 0.0215(3) Uani 1 1 d . A .
C5 C 0.22924(16) 0.49691(11) 0.42015(9) 0.0245(3) Uani 1 1 d . . .
C12 C 0.27035(17) 0.49043(12) 0.51021(9) 0.0259(3) Uani 1 1 d . A .
H7 H 0.2312 0.5400 0.5487 0.031 Uiso 1 1 calc R . .
C6 C 0.36915(16) 0.41070(11) 0.54281(9) 0.0216(3) Uani 1 1 d . . .
C11 C 0.42534(17) 0.33657(11) 0.48800(10) 0.0249(3) Uani 1 1 d . A .
H8 H 0.4927 0.2816 0.5120 0.030 Uiso 1 1 calc R . .
C7 C 0.38264(16) 0.34315(11) 0.39804(10) 0.0253(3) Uani 1 1 d . . .
H9 H 0.4206 0.2920 0.3604 0.030 Uiso 1 1 calc R A .
C14 C 0.2860(2) 0.35597(13) 0.21643(10) 0.0348(4) Uani 1 1 d . A .
H10 H 0.4004 0.3531 0.2210 0.052 Uiso 1 1 calc R . .
H11 H 0.2433 0.3734 0.1557 0.052 Uiso 1 1 calc R . .
H12 H 0.2456 0.2872 0.2325 0.052 Uiso 1 1 calc R . .
O1 O 0.23981(12) 0.43569(8) 0.27527(6) 0.0274(2) Uani 1 1 d . . .
O6A O 0.1108(5) 0.6106(5) 0.3154(4) 0.0335(10) Uani 0.663(3) 1 d P A 1
O11B O 0.0611(13) 0.5938(11) 0.3179(9) 0.065(3) Uani 0.337(3) 1 d P A 2
O10A O 0.0227(2) 0.60550(15) 0.44103(11) 0.0418(6) Uani 0.663(3) 1 d P A 1
O10B O 0.1632(4) 0.6774(3) 0.4328(2) 0.0415(13) Uani 0.337(3) 1 d P A 2
N4A N 0.1128(9) 0.5760(6) 0.3912(7) 0.0261(12) Uani 0.663(3) 1 d P A 1
N4B N 0.1460(18) 0.5977(12) 0.3835(13) 0.030(2) Uani 0.337(3) 1 d P A 2
O3 O 0.36606(14) 0.47177(10) 0.68506(7) 0.0416(3) Uani 1 1 d . . .
O2 O 0.50451(13) 0.33306(9) 0.66628(7) 0.0347(3) Uani 1 1 d . . .
N1 N 0.41613(14) 0.40456(10) 0.63773(8) 0.0258(3) Uani 1 1 d . A .


_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
C4 O4 1.3382(17) . ?
C4 C8 1.399(2) . ?
C4 C10 1.4101(19) . ?
C10 C2 1.379(2) . ?
C10 N3 1.4652(19) . ?
C2 C9 1.381(2) . ?
C2 H1 0.9500 . ?
C9 C1 1.381(2) . ?
C9 N2 1.4609(18) . ?
C1 C8 1.379(2) . ?
C1 H2 0.9500 . ?
C8 H3 0.9500 . ?
C13 O4 1.4403(18) . ?
C13 H4 0.9800 . ?
C13 H5 0.9800 . ?
C13 H6 0.9800 . ?
O9 N3 1.2271(17) . ?
O7 N3 1.2236(17) . ?
O8 N2 1.2280(16) . ?
O5 N2 1.2264(17) . ?
C3 O1 1.3356(17) . ?
C3 C7 1.400(2) . ?
C3 C5 1.407(2) . ?
C5 C12 1.381(2) . ?
C5 N4A 1.447(10) . ?
C5 N4B 1.534(17) . ?
C12 C6 1.374(2) . ?
C12 H7 0.9500 . ?
C6 C11 1.384(2) . ?
C6 N1 1.4595(18) . ?
C11 C7 1.381(2) . ?
C11 H8 0.9500 . ?
C7 H9 0.9500 . ?
C14 O1 1.4395(17) . ?
C14 H10 0.9800 . ?
C14 H11 0.9800 . ?
C14 H12 0.9800 . ?
O6A N4A 1.236(11) . ?
O11B N4B 1.17(3) . ?
O10A N4A 1.211(9) . ?
O10B N4B 1.257(19) . ?
O3 N1 1.2285(16) . ?
O2 N1 1.2276(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 C4 C8 123.97(13) . . ?
O4 C4 C10 118.56(12) . . ?
C8 C4 C10 117.45(13) . . ?
C2 C10 C4 122.67(13) . . ?
C2 C10 N3 116.74(13) . . ?
C4 C10 N3 120.58(13) . . ?
C10 C2 C9 117.49(13) . . ?
C10 C2 H1 121.3 . . ?
C9 C2 H1 121.3 . . ?
C1 C9 C2 121.86(13) . . ?
C1 C9 N2 119.00(13) . . ?
C2 C9 N2 119.13(13) . . ?
C8 C1 C9 120.05(13) . . ?
C8 C1 H2 120.0 . . ?
C9 C1 H2 120.0 . . ?
C1 C8 C4 120.41(13) . . ?
C1 C8 H3 119.8 . . ?
C4 C8 H3 119.8 . . ?
O4 C13 H4 109.5 . . ?
O4 C13 H5 109.5 . . ?
H4 C13 H5 109.5 . . ?
O4 C13 H6 109.5 . . ?
H4 C13 H6 109.5 . . ?
H5 C13 H6 109.5 . . ?
C4 O4 C13 117.79(12) . . ?
O7 N3 O9 124.11(13) . . ?
O7 N3 C10 117.26(13) . . ?
O9 N3 C10 118.63(13) . . ?
O5 N2 O8 123.56(13) . . ?
O5 N2 C9 117.64(13) . . ?
O8 N2 C9 118.80(12) . . ?
O1 C3 C7 124.07(13) . . ?
O1 C3 C5 118.53(12) . . ?
C7 C3 C5 117.40(13) . . ?
C12 C5 C3 122.00(13) . . ?
C12 C5 N4A 115.5(4) . . ?
C3 C5 N4A 122.2(4) . . ?
C12 C5 N4B 117.7(8) . . ?
C3 C5 N4B 119.4(8) . . ?
N4A C5 N4B 16.0(6) . . ?
C6 C12 C5 118.49(13) . . ?
C6 C12 H7 120.8 . . ?
C5 C12 H7 120.8 . . ?
C12 C6 C11 121.70(13) . . ?
C12 C6 N1 118.93(12) . . ?
C11 C6 N1 119.37(12) . . ?
C7 C11 C6 119.43(13) . . ?
C7 C11 H8 120.3 . . ?
C6 C11 H8 120.3 . . ?
C11 C7 C3 120.97(13) . . ?
C11 C7 H9 119.5 . . ?
C3 C7 H9 119.5 . . ?
O1 C14 H10 109.5 . . ?
O1 C14 H11 109.5 . . ?
H10 C14 H11 109.5 . . ?
O1 C14 H12 109.5 . . ?
H10 C14 H12 109.5 . . ?
H11 C14 H12 109.5 . . ?
C3 O1 C14 118.14(11) . . ?
O10A N4A O6A 122.9(8) . . ?
O10A N4A C5 119.6(7) . . ?
O6A N4A C5 117.5(7) . . ?
O11B N4B O10B 124.3(16) . . ?
O11B N4B C5 119.6(15) . . ?
O10B N4B C5 115.7(15) . . ?
O2 N1 O3 123.24(12) . . ?
O2 N1 C6 118.48(12) . . ?
O3 N1 C6 118.28(11) . . ?

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
O4 C4 C10 C2 178.63(13) . . . . ?
C8 C4 C10 C2 -0.3(2) . . . . ?
O4 C4 C10 N3 -0.4(2) . . . . ?
C8 C4 C10 N3 -179.36(12) . . . . ?
C4 C10 C2 C9 2.0(2) . . . . ?
N3 C10 C2 C9 -178.86(12) . . . . ?
C10 C2 C9 C1 -1.9(2) . . . . ?
C10 C2 C9 N2 177.12(12) . . . . ?
C2 C9 C1 C8 0.0(2) . . . . ?
N2 C9 C1 C8 -179.00(12) . . . . ?
C9 C1 C8 C4 1.8(2) . . . . ?
O4 C4 C8 C1 179.48(13) . . . . ?
C10 C4 C8 C1 -1.7(2) . . . . ?
C8 C4 O4 C13 12.9(2) . . . . ?
C10 C4 O4 C13 -165.90(13) . . . . ?
C2 C10 N3 O7 -33.68(19) . . . . ?
C4 C10 N3 O7 145.45(14) . . . . ?
C2 C10 N3 O9 145.27(14) . . . . ?
C4 C10 N3 O9 -35.60(19) . . . . ?
C1 C9 N2 O5 7.0(2) . . . . ?
C2 C9 N2 O5 -172.02(13) . . . . ?
C1 C9 N2 O8 -173.25(13) . . . . ?
C2 C9 N2 O8 7.7(2) . . . . ?
O1 C3 C5 C12 -179.76(13) . . . . ?
C7 C3 C5 C12 0.4(2) . . . . ?
O1 C3 C5 N4A 7.3(3) . . . . ?
C7 C3 C5 N4A -172.5(3) . . . . ?
O1 C3 C5 N4B -11.1(6) . . . . ?
C7 C3 C5 N4B 169.1(6) . . . . ?
C3 C5 C12 C6 0.6(2) . . . . ?
N4A C5 C12 C6 174.0(3) . . . . ?
N4B C5 C12 C6 -168.3(5) . . . . ?
C5 C12 C6 C11 -1.2(2) . . . . ?
C5 C12 C6 N1 178.64(13) . . . . ?
C12 C6 C11 C7 0.7(2) . . . . ?
N1 C6 C11 C7 -179.13(12) . . . . ?
C6 C11 C7 C3 0.4(2) . . . . ?
O1 C3 C7 C11 179.27(13) . . . . ?
C5 C3 C7 C11 -0.9(2) . . . . ?
C7 C3 O1 C14 4.8(2) . . . . ?
C5 C3 O1 C14 -174.95(13) . . . . ?
C12 C5 N4A O10A -24.4(7) . . . . ?
C3 C5 N4A O10A 149.0(5) . . . . ?
N4B C5 N4A O10A -126(5) . . . . ?
C12 C5 N4A O6A 155.5(6) . . . . ?
C3 C5 N4A O6A -31.1(7) . . . . ?
N4B C5 N4A O6A 54(4) . . . . ?
C12 C5 N4B O11B -152.2(12) . . . . ?
C3 C5 N4B O11B 38.6(15) . . . . ?
N4A C5 N4B O11B -66(4) . . . . ?
C12 C5 N4B O10B 20.6(11) . . . . ?
C3 C5 N4B O10B -148.6(8) . . . . ?
N4A C5 N4B O10B 107(5) . . . . ?
C12 C6 N1 O2 -179.97(13) . . . . ?
C11 C6 N1 O2 -0.17(19) . . . . ?
C12 C6 N1 O3 -0.49(19) . . . . ?
C11 C6 N1 O3 179.31(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.041
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24DNAN_a_163K
_database_code_depnum_ccdc_archive 'CCDC 1401652'
_audit_update_record             
;
2015-05-18 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.623(4)
_cell_length_b                   12.646(5)
_cell_length_c                   15.305(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.145(5)
_cell_angle_gamma                90.00
_cell_volume                     1656.0(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4446
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9702
_exptl_absorpt_correction_T_max  0.9796
_exptl_absorpt_process_details   
;CrystalClear (Rigaku Americas and Rigaku, 2009)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13221
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3789
_reflns_number_gt                2989
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0474P)²+0.3366P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3789
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.69532(18) 0.42611(12) 0.52957(10) 0.0269(3) Uani 1 1 d . . .
C2 C 0.80751(18) 0.48004(12) 0.58837(10) 0.0266(3) Uani 1 1 d . . .
C3 C 0.85201(17) 0.44603(13) 0.67322(10) 0.0275(3) Uani 1 1 d . . .
H1 H 0.9302 0.4822 0.7111 0.033 Uiso 1 1 calc R . .
C4 C 0.77909(17) 0.35762(12) 0.70124(10) 0.0268(3) Uani 1 1 d . . .
C5 C 0.66856(18) 0.30211(12) 0.64625(11) 0.0290(3) Uani 1 1 d . . .
H2 H 0.6203 0.2413 0.6674 0.035 Uiso 1 1 calc R . .
C6 C 0.62867(18) 0.33541(12) 0.56058(10) 0.0290(3) Uani 1 1 d . . .
H3 H 0.5549 0.2960 0.5223 0.035 Uiso 1 1 calc R . .
C7 C 0.5758(2) 0.39609(15) 0.38280(12) 0.0453(5) Uani 1 1 d . . .
H4 H 0.6287 0.3276 0.3818 0.068 Uiso 1 1 calc R . .
H5 H 0.5707 0.4293 0.3247 0.068 Uiso 1 1 calc R . .
H6 H 0.4697 0.3855 0.3978 0.068 Uiso 1 1 calc R . .
O1 O 0.66162(14) 0.46358(9) 0.44775(7) 0.0348(3) Uani 1 1 d . . .
O2 O 0.80736(17) 0.63603(10) 0.50908(8) 0.0486(4) Uani 1 1 d . . .
O3 O 1.01919(16) 0.59008(11) 0.59061(10) 0.0527(4) Uani 1 1 d . . .
O4 O 0.92705(15) 0.36457(11) 0.83833(8) 0.0468(3) Uani 1 1 d . . .
O5 O 0.74003(17) 0.25045(12) 0.81805(9) 0.0559(4) Uani 1 1 d . . .
N1 N 0.88350(17) 0.57552(11) 0.56022(9) 0.0341(3) Uani 1 1 d . . .
N2 N 0.81852(16) 0.32183(12) 0.79213(9) 0.0356(3) Uani 1 1 d . . .
C8 C 0.78393(17) 0.07609(12) 0.36176(10) 0.0250(3) Uani 1 1 d . A .
C9 C 0.72985(17) 0.00333(12) 0.42069(10) 0.0272(3) Uani 1 1 d . . .
C10 C 0.77080(18) 0.00986(13) 0.51034(10) 0.0292(3) Uani 1 1 d . A .
H7 H 0.7318 -0.0398 0.5488 0.035 Uiso 1 1 calc R . .
C11 C 0.86926(17) 0.08974(12) 0.54292(10) 0.0250(3) Uani 1 1 d . . .
C12 C 0.92486(18) 0.16347(12) 0.48813(11) 0.0292(3) Uani 1 1 d . A .
H8 H 0.9922 0.2185 0.5121 0.035 Uiso 1 1 calc R . .
C13 C 0.88217(18) 0.15683(12) 0.39843(10) 0.0288(3) Uani 1 1 d . . .
H9 H 0.9201 0.2080 0.3609 0.035 Uiso 1 1 calc R A .
C14 C 0.7850(2) 0.14364(15) 0.21678(11) 0.0418(4) Uani 1 1 d . A .
H10 H 0.7446 0.2126 0.2326 0.063 Uiso 1 1 calc R . .
H11 H 0.7423 0.1259 0.1562 0.063 Uiso 1 1 calc R . .
H12 H 0.8993 0.1466 0.2214 0.063 Uiso 1 1 calc R . .
O6 O 0.73927(13) 0.06413(9) 0.27578(7) 0.0324(3) Uani 1 1 d . . .
O7A O 0.6116(6) -0.1098(5) 0.3154(4) 0.0417(11) Uani 0.652(4) 1 d P A 1
O7B O 0.5606(14) -0.0939(10) 0.3203(9) 0.078(4) Uani 0.348(4) 1 d P A 2
O8A O 0.5243(3) -0.10509(17) 0.44105(13) 0.0499(8) Uani 0.652(4) 1 d P A 1
O8B O 0.6624(5) -0.1763(3) 0.4335(2) 0.0491(14) Uani 0.348(4) 1 d P A 2
N3A N 0.6127(7) -0.0813(5) 0.3921(5) 0.0271(11) Uani 0.652(4) 1 d P A 1
N3B N 0.6514(16) -0.0864(13) 0.3822(12) 0.052(4) Uani 0.348(4) 1 d P A 2
O9 O 0.86672(16) 0.02878(11) 0.68496(8) 0.0499(4) Uani 1 1 d . . .
O10 O 1.00447(15) 0.16715(10) 0.66616(8) 0.0418(3) Uani 1 1 d . . .
N4 N 0.91633(15) 0.09569(11) 0.63779(9) 0.0307(3) Uani 1 1 d . A .


_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 O1 1.3367(19) . ?
C1 C6 1.392(2) . ?
C1 C2 1.412(2) . ?
C2 C3 1.376(2) . ?
C2 N1 1.464(2) . ?
C3 C4 1.377(2) . ?
C3 H1 0.9500 . ?
C4 C5 1.382(2) . ?
C4 N2 1.462(2) . ?
C5 C6 1.379(2) . ?
C5 H2 0.9500 . ?
C6 H3 0.9500 . ?
C7 O1 1.443(2) . ?
C7 H4 0.9800 . ?
C7 H5 0.9800 . ?
C7 H6 0.9800 . ?
O2 N1 1.2254(19) . ?
O3 N1 1.218(2) . ?
O4 N2 1.2260(18) . ?
O5 N2 1.2236(19) . ?
C8 O6 1.3329(18) . ?
C8 C13 1.399(2) . ?
C8 C9 1.408(2) . ?
C9 C10 1.376(2) . ?
C9 N3B 1.412(16) . ?
C9 N3A 1.499(5) . ?
C10 C11 1.373(2) . ?
C10 H7 0.9500 . ?
C11 C12 1.379(2) . ?
C11 N4 1.460(2) . ?
C12 C13 1.379(2) . ?
C12 H8 0.9500 . ?
C13 H9 0.9500 . ?
C14 O6 1.439(2) . ?
C14 H10 0.9800 . ?
C14 H11 0.9800 . ?
C14 H12 0.9800 . ?
O7A N3A 1.228(9) . ?
O7B N3B 1.16(2) . ?
O8A N3A 1.172(7) . ?
O8B N3B 1.378(18) . ?
O9 N4 1.2234(18) . ?
O10 N4 1.2250(17) . ?

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 C6 124.08(14) . . ?
O1 C1 C2 118.54(14) . . ?
C6 C1 C2 117.36(14) . . ?
C3 C2 C1 122.61(14) . . ?
C3 C2 N1 116.93(14) . . ?
C1 C2 N1 120.46(14) . . ?
C2 C3 C4 117.58(14) . . ?
C2 C3 H1 121.2 . . ?
C4 C3 H1 121.2 . . ?
C3 C4 C5 121.99(14) . . ?
C3 C4 N2 119.11(14) . . ?
C5 C4 N2 118.90(14) . . ?
C6 C5 C4 119.69(14) . . ?
C6 C5 H2 120.2 . . ?
C4 C5 H2 120.2 . . ?
C5 C6 C1 120.72(14) . . ?
C5 C6 H3 119.6 . . ?
C1 C6 H3 119.6 . . ?
O1 C7 H4 109.5 . . ?
O1 C7 H5 109.5 . . ?
H4 C7 H5 109.5 . . ?
O1 C7 H6 109.5 . . ?
H4 C7 H6 109.5 . . ?
H5 C7 H6 109.5 . . ?
C1 O1 C7 117.97(13) . . ?
O3 N1 O2 124.22(15) . . ?
O3 N1 C2 117.14(15) . . ?
O2 N1 C2 118.63(14) . . ?
O5 N2 O4 123.47(15) . . ?
O5 N2 C4 117.67(14) . . ?
O4 N2 C4 118.86(14) . . ?
O6 C8 C13 124.40(14) . . ?
O6 C8 C9 118.71(13) . . ?
C13 C8 C9 116.89(14) . . ?
C10 C9 C8 122.35(14) . . ?
C10 C9 N3B 120.9(8) . . ?
C8 C9 N3B 116.0(7) . . ?
C10 C9 N3A 114.4(3) . . ?
C8 C9 N3A 123.0(3) . . ?
N3B C9 N3A 14.9(7) . . ?
C11 C10 C9 118.48(14) . . ?
C11 C10 H7 120.8 . . ?
C9 C10 H7 120.8 . . ?
C10 C11 C12 121.51(14) . . ?
C10 C11 N4 118.82(13) . . ?
C12 C11 N4 119.68(13) . . ?
C13 C12 C11 119.61(14) . . ?
C13 C12 H8 120.2 . . ?
C11 C12 H8 120.2 . . ?
C12 C13 C8 121.14(14) . . ?
C12 C13 H9 119.4 . . ?
C8 C13 H9 119.4 . . ?
O6 C14 H10 109.5 . . ?
O6 C14 H11 109.5 . . ?
H10 C14 H11 109.5 . . ?
O6 C14 H12 109.5 . . ?
H10 C14 H12 109.5 . . ?
H11 C14 H12 109.5 . . ?
C8 O6 C14 118.17(13) . . ?
O8A N3A O7A 127.4(6) . . ?
O8A N3A C9 117.7(5) . . ?
O7A N3A C9 114.4(5) . . ?
O7B N3B O8B 113.1(13) . . ?
O7B N3B C9 130.4(16) . . ?
O8B N3B C9 115.5(13) . . ?
O9 N4 O10 123.24(14) . . ?
O9 N4 C11 118.48(13) . . ?
O10 N4 C11 118.28(13) . . ?

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 -178.60(14) . . . . ?
C6 C1 C2 C3 0.2(2) . . . . ?
O1 C1 C2 N1 0.7(2) . . . . ?
C6 C1 C2 N1 179.52(14) . . . . ?
C1 C2 C3 C4 -2.1(2) . . . . ?
N1 C2 C3 C4 178.63(13) . . . . ?
C2 C3 C4 C5 2.0(2) . . . . ?
C2 C3 C4 N2 -177.41(14) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
N2 C4 C5 C6 179.30(14) . . . . ?
C4 C5 C6 C1 -1.8(2) . . . . ?
O1 C1 C6 C5 -179.50(14) . . . . ?
C2 C1 C6 C5 1.7(2) . . . . ?
C6 C1 O1 C7 -12.8(2) . . . . ?
C2 C1 O1 C7 165.97(15) . . . . ?
C3 C2 N1 O3 33.5(2) . . . . ?
C1 C2 N1 O3 -145.79(16) . . . . ?
C3 C2 N1 O2 -145.53(15) . . . . ?
C1 C2 N1 O2 35.1(2) . . . . ?
C3 C4 N2 O5 172.11(15) . . . . ?
C5 C4 N2 O5 -7.3(2) . . . . ?
C3 C4 N2 O4 -7.6(2) . . . . ?
C5 C4 N2 O4 172.96(14) . . . . ?
O6 C8 C9 C10 179.80(14) . . . . ?
C13 C8 C9 C10 -0.2(2) . . . . ?
O6 C8 C9 N3B 9.4(7) . . . . ?
C13 C8 C9 N3B -170.5(7) . . . . ?
O6 C8 C9 N3A -5.7(4) . . . . ?
C13 C8 C9 N3A 174.3(3) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
N3B C9 C10 C11 169.2(7) . . . . ?
N3A C9 C10 C11 -175.6(3) . . . . ?
C9 C10 C11 C12 1.1(2) . . . . ?
C9 C10 C11 N4 -178.52(14) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
N4 C11 C12 C13 179.04(14) . . . . ?
C11 C12 C13 C8 -0.4(2) . . . . ?
O6 C8 C13 C12 -179.25(14) . . . . ?
C9 C8 C13 C12 0.7(2) . . . . ?
C13 C8 O6 C14 -4.9(2) . . . . ?
C9 C8 O6 C14 175.14(14) . . . . ?
C10 C9 N3A O8A 28.7(7) . . . . ?
C8 C9 N3A O8A -146.2(5) . . . . ?
N3B C9 N3A O8A 148(5) . . . . ?
C10 C9 N3A O7A -158.5(5) . . . . ?
C8 C9 N3A O7A 26.6(7) . . . . ?
N3B C9 N3A O7A -39(4) . . . . ?
C10 C9 N3B O7B 147.9(15) . . . . ?
C8 C9 N3B O7B -41.6(19) . . . . ?
N3A C9 N3B O7B 80(4) . . . . ?
C10 C9 N3B O8B -19.4(13) . . . . ?
C8 C9 N3B O8B 151.1(7) . . . . ?
N3A C9 N3B O8B -87(4) . . . . ?
C10 C11 N4 O9 0.3(2) . . . . ?
C12 C11 N4 O9 -179.28(15) . . . . ?
C10 C11 N4 O10 179.85(14) . . . . ?
C12 C11 N4 O10 0.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.040
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24DNAN_a_183K
_database_code_depnum_ccdc_archive 'CCDC 1401653'
_audit_update_record             
;
2015-05-18 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.665(3)
_cell_length_b                   12.666(4)
_cell_length_c                   15.316(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.277(3)
_cell_angle_gamma                90.00
_cell_volume                     1667.4(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    183(2)
_cell_measurement_reflns_used    4341
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9704
_exptl_absorpt_correction_T_max  0.9797
_exptl_absorpt_process_details   
;CrystalClear (Rigaku Americas and Rigaku, 2009)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      183(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13280
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.46
_reflns_number_total             3798
_reflns_number_gt                2914
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0519P)²+0.3298P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3798
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1150
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_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 0.69559(19) 0.42594(13) 0.02986(11) 0.0306(4) Uani 1 1 d . . .
C2 C 0.80723(19) 0.47943(13) 0.08858(11) 0.0304(4) Uani 1 1 d . . .
C3 C 0.85141(19) 0.44565(13) 0.17346(11) 0.0314(4) Uani 1 1 d . . .
H1 H 0.9293 0.4819 0.2113 0.038 Uiso 1 1 calc R . .
C4 C 0.77880(19) 0.35753(13) 0.20167(11) 0.0318(4) Uani 1 1 d . . .
C5 C 0.66760(19) 0.30255(13) 0.14644(12) 0.0339(4) Uani 1 1 d . . .
H2 H 0.6185 0.2423 0.1676 0.041 Uiso 1 1 calc R . .
C6 C 0.62866(19) 0.33558(13) 0.06088(11) 0.0339(4) Uani 1 1 d . . .
H3 H 0.5553 0.2963 0.0225 0.041 Uiso 1 1 calc R . .
C7 C 0.5762(3) 0.39608(17) -0.11676(13) 0.0531(5) Uani 1 1 d . . .
H4 H 0.6289 0.3277 -0.1182 0.080 Uiso 1 1 calc R . .
H5 H 0.5701 0.4296 -0.1748 0.080 Uiso 1 1 calc R . .
H6 H 0.4709 0.3853 -0.1014 0.080 Uiso 1 1 calc R . .
O1 O 0.66233(15) 0.46299(10) -0.05204(8) 0.0414(3) Uani 1 1 d . . .
O2 O 0.8083(2) 0.63508(11) 0.00916(9) 0.0578(4) Uani 1 1 d . . .
O3 O 1.01845(17) 0.58942(12) 0.09136(11) 0.0622(4) Uani 1 1 d . . .
O4 O 0.92596(16) 0.36420(13) 0.33833(9) 0.0549(4) Uani 1 1 d . . .
O5 O 0.7393(2) 0.25083(13) 0.31817(10) 0.0671(5) Uani 1 1 d . . .
N1 N 0.88374(19) 0.57467(12) 0.06065(10) 0.0397(4) Uani 1 1 d . . .
N2 N 0.81773(18) 0.32191(13) 0.29224(10) 0.0420(4) Uani 1 1 d . . .
C8 C 0.78338(18) 0.07612(13) -0.13779(11) 0.0290(4) Uani 1 1 d . A .
C9 C 0.73017(19) 0.00337(13) -0.07918(11) 0.0315(4) Uani 1 1 d . . .
C10 C 0.77150(19) 0.01011(14) 0.01054(11) 0.0331(4) Uani 1 1 d . A .
H7 H 0.7332 -0.0395 0.0491 0.040 Uiso 1 1 calc R . .
C11 C 0.86934(18) 0.09013(13) 0.04298(10) 0.0295(4) Uani 1 1 d . . .
C12 C 0.9244(2) 0.16390(13) -0.01189(12) 0.0343(4) Uani 1 1 d . A .
H8 H 0.9914 0.2189 0.0120 0.041 Uiso 1 1 calc R . .
C13 C 0.88139(19) 0.15708(13) -0.10144(11) 0.0342(4) Uani 1 1 d . . .
H9 H 0.9188 0.2081 -0.1391 0.041 Uiso 1 1 calc R A .
C14 C 0.7839(3) 0.14323(17) -0.28291(12) 0.0493(5) Uani 1 1 d . A .
H10 H 0.7431 0.2120 -0.2675 0.074 Uiso 1 1 calc R . .
H11 H 0.7417 0.1251 -0.3434 0.074 Uiso 1 1 calc R . .
H12 H 0.8977 0.1466 -0.2781 0.074 Uiso 1 1 calc R . .
O6 O 0.73877(14) 0.06400(10) -0.22376(7) 0.0378(3) Uani 1 1 d . . .
O7A O 0.6117(8) -0.1097(5) -0.1839(4) 0.0514(14) Uani 0.630(4) 1 d P A 1
O7B O 0.5630(16) -0.0948(10) -0.1790(8) 0.095(5) Uani 0.370(4) 1 d P A 2
O8A O 0.5253(3) -0.1049(2) -0.05866(15) 0.0582(10) Uani 0.630(4) 1 d P A 1
O8B O 0.6621(6) -0.1753(3) -0.0664(3) 0.0616(17) Uani 0.370(4) 1 d P A 2
N3A N 0.6161(15) -0.0742(8) -0.1099(10) 0.0355(17) Uani 0.630(4) 1 d P A 1
N3B N 0.643(3) -0.0985(13) -0.1118(18) 0.042(4) Uani 0.370(4) 1 d P A 2
O9 O 0.86768(18) 0.02959(13) 0.18481(8) 0.0590(4) Uani 1 1 d . . .
O10 O 1.00448(16) 0.16748(11) 0.16600(9) 0.0497(4) Uani 1 1 d . . .
N4 N 0.91666(17) 0.09634(12) 0.13766(10) 0.0362(3) Uani 1 1 d . A .


_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 O1 1.336(2) . ?
C1 C6 1.394(2) . ?
C1 C2 1.408(2) . ?
C2 C3 1.376(2) . ?
C2 N1 1.466(2) . ?
C3 C4 1.377(2) . ?
C3 H1 0.9500 . ?
C4 C5 1.387(2) . ?
C4 N2 1.457(2) . ?
C5 C6 1.376(2) . ?
C5 H2 0.9500 . ?
C6 H3 0.9500 . ?
C7 O1 1.439(2) . ?
C7 H4 0.9800 . ?
C7 H5 0.9800 . ?
C7 H6 0.9800 . ?
O2 N1 1.226(2) . ?
O3 N1 1.216(2) . ?
O4 N2 1.224(2) . ?
O5 N2 1.224(2) . ?
C8 O6 1.333(2) . ?
C8 C13 1.401(2) . ?
C8 C9 1.404(2) . ?
C9 C10 1.378(2) . ?
C9 N3A 1.430(14) . ?
C9 N3B 1.55(2) . ?
C10 C11 1.373(2) . ?
C10 H7 0.9500 . ?
C11 C12 1.381(2) . ?
C11 N4 1.458(2) . ?
C12 C13 1.378(2) . ?
C12 H8 0.9500 . ?
C13 H9 0.9500 . ?
C14 O6 1.439(2) . ?
C14 H10 0.9800 . ?
C14 H11 0.9800 . ?
C14 H12 0.9800 . ?
O7A N3A 1.215(16) . ?
O7B N3B 1.17(3) . ?
O8A N3A 1.242(15) . ?
O8B N3B 1.20(2) . ?
O9 N4 1.222(2) . ?
O10 N4 1.2230(19) . ?

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 C6 123.99(15) . . ?
O1 C1 C2 118.66(15) . . ?
C6 C1 C2 117.34(15) . . ?
C3 C2 C1 122.69(15) . . ?
C3 C2 N1 116.72(15) . . ?
C1 C2 N1 120.59(15) . . ?
C2 C3 C4 117.70(15) . . ?
C2 C3 H1 121.1 . . ?
C4 C3 H1 121.1 . . ?
C3 C4 C5 121.69(16) . . ?
C3 C4 N2 119.32(15) . . ?
C5 C4 N2 118.98(15) . . ?
C6 C5 C4 119.72(16) . . ?
C6 C5 H2 120.1 . . ?
C4 C5 H2 120.1 . . ?
C5 C6 C1 120.79(15) . . ?
C5 C6 H3 119.6 . . ?
C1 C6 H3 119.6 . . ?
O1 C7 H4 109.5 . . ?
O1 C7 H5 109.5 . . ?
H4 C7 H5 109.5 . . ?
O1 C7 H6 109.5 . . ?
H4 C7 H6 109.5 . . ?
H5 C7 H6 109.5 . . ?
C1 O1 C7 118.11(15) . . ?
O3 N1 O2 124.05(16) . . ?
O3 N1 C2 117.43(16) . . ?
O2 N1 C2 118.51(16) . . ?
O4 N2 O5 123.45(17) . . ?
O4 N2 C4 118.80(15) . . ?
O5 N2 C4 117.75(16) . . ?
O6 C8 C13 124.20(15) . . ?
O6 C8 C9 118.56(14) . . ?
C13 C8 C9 117.24(15) . . ?
C10 C9 C8 122.13(15) . . ?
C10 C9 N3A 116.9(6) . . ?
C8 C9 N3A 120.6(6) . . ?
C10 C9 N3B 115.4(10) . . ?
C8 C9 N3B 121.9(10) . . ?
N3A C9 N3B 14.2(10) . . ?
C11 C10 C9 118.49(15) . . ?
C11 C10 H7 120.8 . . ?
C9 C10 H7 120.8 . . ?
C10 C11 C12 121.60(15) . . ?
C10 C11 N4 118.85(14) . . ?
C12 C11 N4 119.56(14) . . ?
C13 C12 C11 119.52(15) . . ?
C13 C12 H8 120.2 . . ?
C11 C12 H8 120.2 . . ?
C12 C13 C8 121.02(15) . . ?
C12 C13 H9 119.5 . . ?
C8 C13 H9 119.5 . . ?
O6 C14 H10 109.5 . . ?
O6 C14 H11 109.5 . . ?
H10 C14 H11 109.5 . . ?
O6 C14 H12 109.5 . . ?
H10 C14 H12 109.5 . . ?
H11 C14 H12 109.5 . . ?
C8 O6 C14 118.26(14) . . ?
O7A N3A O8A 121.7(12) . . ?
O7A N3A C9 120.0(12) . . ?
O8A N3A C9 118.3(10) . . ?
O7B N3B O8B 124.8(19) . . ?
O7B N3B C9 117.6(16) . . ?
O8B N3B C9 117.6(18) . . ?
O9 N4 O10 123.16(15) . . ?
O9 N4 C11 118.37(14) . . ?
O10 N4 C11 118.46(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 -178.48(15) . . . . ?
C6 C1 C2 C3 0.2(2) . . . . ?
O1 C1 C2 N1 0.8(2) . . . . ?
C6 C1 C2 N1 179.54(15) . . . . ?
C1 C2 C3 C4 -1.9(2) . . . . ?
N1 C2 C3 C4 178.74(15) . . . . ?
C2 C3 C4 C5 1.5(2) . . . . ?
C2 C3 C4 N2 -177.46(15) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
N2 C4 C5 C6 179.54(15) . . . . ?
C4 C5 C6 C1 -2.3(2) . . . . ?
O1 C1 C6 C5 -179.44(15) . . . . ?
C2 C1 C6 C5 1.9(2) . . . . ?
C6 C1 O1 C7 -12.4(2) . . . . ?
C2 C1 O1 C7 166.23(16) . . . . ?
C3 C2 N1 O3 33.2(2) . . . . ?
C1 C2 N1 O3 -146.12(17) . . . . ?
C3 C2 N1 O2 -145.74(16) . . . . ?
C1 C2 N1 O2 34.9(2) . . . . ?
C3 C4 N2 O4 -7.8(2) . . . . ?
C5 C4 N2 O4 173.15(16) . . . . ?
C3 C4 N2 O5 172.04(17) . . . . ?
C5 C4 N2 O5 -7.0(2) . . . . ?
O6 C8 C9 C10 179.70(16) . . . . ?
C13 C8 C9 C10 0.0(2) . . . . ?
O6 C8 C9 N3A -7.4(5) . . . . ?
C13 C8 C9 N3A 172.9(5) . . . . ?
O6 C8 C9 N3B 9.2(8) . . . . ?
C13 C8 C9 N3B -170.5(8) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
N3A C9 C10 C11 -173.9(4) . . . . ?
N3B C9 C10 C11 170.3(8) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C9 C10 C11 N4 -178.54(15) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
N4 C11 C12 C13 179.08(15) . . . . ?
C11 C12 C13 C8 -0.4(3) . . . . ?
O6 C8 C13 C12 -179.12(16) . . . . ?
C9 C8 C13 C12 0.6(2) . . . . ?
C13 C8 O6 C14 -5.0(2) . . . . ?
C9 C8 O6 C14 175.34(15) . . . . ?
C10 C9 N3A O7A -155.0(8) . . . . ?
C8 C9 N3A O7A 31.7(11) . . . . ?
N3B C9 N3A O7A -68(6) . . . . ?
C10 C9 N3A O8A 23.7(9) . . . . ?
C8 C9 N3A O8A -149.6(6) . . . . ?
N3B C9 N3A O8A 111(7) . . . . ?
C10 C9 N3B O7B 155.8(18) . . . . ?
C8 C9 N3B O7B -33(2) . . . . ?
N3A C9 N3B O7B 56(5) . . . . ?
C10 C9 N3B O8B -25(2) . . . . ?
C8 C9 N3B O8B 146.5(15) . . . . ?
N3A C9 N3B O8B -124(8) . . . . ?
C10 C11 N4 O9 0.3(2) . . . . ?
C12 C11 N4 O9 -179.30(16) . . . . ?
C10 C11 N4 O10 179.61(16) . . . . ?
C12 C11 N4 O10 0.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.039
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24DNAN_a_213K
_database_code_depnum_ccdc_archive 'CCDC 1401654'
_audit_update_record             
;
2015-05-18 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.691(3)
_cell_length_b                   12.673(4)
_cell_length_c                   15.336(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.417(4)
_cell_angle_gamma                90.00
_cell_volume                     1675.0(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    4363
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9706
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_process_details   
;CrystalClear (Rigaku Americas and Rigaku, 2009)
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13317
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3824
_reflns_number_gt                2816
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0546P)²+0.2667P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3824
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6958(2) 0.42555(13) 0.53018(11) 0.0349(4) Uani 1 1 d . . .
C2 C 0.8072(2) 0.47920(13) 0.58885(11) 0.0341(4) Uani 1 1 d . . .
C3 C 0.8508(2) 0.44545(14) 0.67355(11) 0.0357(4) Uani 1 1 d . . .
H1 H 0.9279 0.4811 0.7110 0.043 Uiso 1 1 calc R . .
C4 C 0.7778(2) 0.35759(14) 0.70183(11) 0.0355(4) Uani 1 1 d . . .
C5 C 0.6672(2) 0.30284(14) 0.64662(12) 0.0391(4) Uani 1 1 d . . .
H2 H 0.6188 0.2432 0.6674 0.047 Uiso 1 1 calc R . .
C6 C 0.6282(2) 0.33587(14) 0.56119(12) 0.0397(4) Uani 1 1 d . . .
H3 H 0.5550 0.2974 0.5233 0.048 Uiso 1 1 calc R . .
C7 C 0.5766(3) 0.39566(18) 0.38369(14) 0.0613(6) Uani 1 1 d . . .
H4 H 0.6273 0.3276 0.3828 0.092 Uiso 1 1 calc R . .
H5 H 0.5716 0.4283 0.3262 0.092 Uiso 1 1 calc R . .
H6 H 0.4723 0.3862 0.3985 0.092 Uiso 1 1 calc R . .
O1 O 0.66328(16) 0.46228(10) 0.44831(8) 0.0476(3) Uani 1 1 d . . .
O2 O 0.8094(2) 0.63427(12) 0.50914(10) 0.0675(5) Uani 1 1 d . . .
O3 O 1.01763(19) 0.58898(13) 0.59198(12) 0.0716(5) Uani 1 1 d . . .
O4 O 0.92524(18) 0.36378(14) 0.83843(9) 0.0629(4) Uani 1 1 d . . .
O5 O 0.7386(2) 0.25141(15) 0.81812(11) 0.0774(5) Uani 1 1 d . . .
N1 N 0.8840(2) 0.57406(12) 0.56108(10) 0.0449(4) Uani 1 1 d . . .
N2 N 0.8173(2) 0.32215(14) 0.79249(11) 0.0478(4) Uani 1 1 d . . .
C8 C 0.78335(19) 0.07625(13) 0.36248(11) 0.0328(4) Uani 1 1 d . A .
C9 C 0.7303(2) 0.00380(13) 0.42112(11) 0.0353(4) Uani 1 1 d . . .
C10 C 0.7720(2) 0.01031(14) 0.51068(11) 0.0361(4) Uani 1 1 d . A .
H7 H 0.7348 -0.0389 0.5488 0.043 Uiso 1 1 calc R . .
C11 C 0.86930(19) 0.09038(13) 0.54298(11) 0.0329(4) Uani 1 1 d . . .
C12 C 0.9239(2) 0.16392(13) 0.48826(12) 0.0387(4) Uani 1 1 d . A .
H8 H 0.9902 0.2183 0.5118 0.046 Uiso 1 1 calc R . .
C13 C 0.8807(2) 0.15707(13) 0.39890(12) 0.0381(4) Uani 1 1 d . . .
H9 H 0.9172 0.2076 0.3617 0.046 Uiso 1 1 calc R A .
C14 C 0.7830(3) 0.14274(18) 0.21754(13) 0.0559(6) Uani 1 1 d . A .
H10 H 0.7451 0.2112 0.2335 0.084 Uiso 1 1 calc R . .
H11 H 0.7388 0.1255 0.1579 0.084 Uiso 1 1 calc R . .
H12 H 0.8952 0.1448 0.2212 0.084 Uiso 1 1 calc R . .
O6 O 0.73831(15) 0.06404(10) 0.27672(8) 0.0435(3) Uani 1 1 d . . .
O7A O 0.6140(8) -0.1102(6) 0.3166(5) 0.0566(15) Uani 0.615(5) 1 d P A 1
O8A O 0.5261(3) -0.1048(2) 0.44147(16) 0.0653(11) Uani 0.615(5) 1 d P A 1
O7B O 0.5602(15) -0.0932(10) 0.3223(8) 0.101(5) Uani 0.385(5) 1 d P A 2
O8B O 0.6613(6) -0.1741(3) 0.4341(3) 0.070(2) Uani 0.385(5) 1 d P A 2
O9 O 0.8681(2) 0.02999(14) 0.68479(9) 0.0678(5) Uani 1 1 d . . .
O10 O 1.00406(18) 0.16788(11) 0.66591(9) 0.0579(4) Uani 1 1 d . . .
N3A N 0.620(2) -0.0763(13) 0.3932(15) 0.045(2) Uani 0.615(5) 1 d P A 1
N4 N 0.91652(18) 0.09670(13) 0.63775(10) 0.0417(4) Uani 1 1 d . A .
N3B N 0.638(3) -0.095(2) 0.384(2) 0.051(5) Uani 0.385(5) 1 d P A 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 O1 1.335(2) . ?
C1 C6 1.391(2) . ?
C1 C2 1.409(2) . ?
C2 C3 1.374(2) . ?
C2 N1 1.465(2) . ?
C3 C4 1.379(2) . ?
C3 H1 0.9400 . ?
C4 C5 1.383(2) . ?
C4 N2 1.459(2) . ?
C5 C6 1.376(3) . ?
C5 H2 0.9400 . ?
C6 H3 0.9400 . ?
C7 O1 1.439(2) . ?
C7 H4 0.9700 . ?
C7 H5 0.9700 . ?
C7 H6 0.9700 . ?
O2 N1 1.226(2) . ?
O3 N1 1.211(2) . ?
O4 N2 1.218(2) . ?
O5 N2 1.223(2) . ?
C8 O6 1.332(2) . ?
C8 C13 1.398(2) . ?
C8 C9 1.404(2) . ?
C9 C10 1.377(2) . ?
C9 N3A 1.426(17) . ?
C9 N3B 1.55(2) . ?
C10 C11 1.372(2) . ?
C10 H7 0.9400 . ?
C11 C12 1.379(2) . ?
C11 N4 1.461(2) . ?
C12 C13 1.376(3) . ?
C12 H8 0.9400 . ?
C13 H9 0.9400 . ?
C14 O6 1.435(2) . ?
C14 H10 0.9700 . ?
C14 H11 0.9700 . ?
C14 H12 0.9700 . ?
O7A N3A 1.25(2) . ?
O8A N3A 1.222(18) . ?
O7B N3B 1.09(4) . ?
O8B N3B 1.26(3) . ?
O9 N4 1.221(2) . ?
O10 N4 1.222(2) . ?

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 C6 123.97(16) . . ?
O1 C1 C2 118.51(16) . . ?
C6 C1 C2 117.51(16) . . ?
C3 C2 C1 122.44(16) . . ?
C3 C2 N1 116.77(15) . . ?
C1 C2 N1 120.78(16) . . ?
C2 C3 C4 117.85(16) . . ?
C2 C3 H1 121.1 . . ?
C4 C3 H1 121.1 . . ?
C3 C4 C5 121.62(16) . . ?
C3 C4 N2 119.15(16) . . ?
C5 C4 N2 119.23(16) . . ?
C6 C5 C4 119.80(16) . . ?
C6 C5 H2 120.1 . . ?
C4 C5 H2 120.1 . . ?
C5 C6 C1 120.73(16) . . ?
C5 C6 H3 119.6 . . ?
C1 C6 H3 119.6 . . ?
O1 C7 H4 109.5 . . ?
O1 C7 H5 109.5 . . ?
H4 C7 H5 109.5 . . ?
O1 C7 H6 109.5 . . ?
H4 C7 H6 109.5 . . ?
H5 C7 H6 109.5 . . ?
C1 O1 C7 118.16(16) . . ?
O3 N1 O2 123.82(17) . . ?
O3 N1 C2 117.65(17) . . ?
O2 N1 C2 118.52(17) . . ?
O4 N2 O5 123.53(17) . . ?
O4 N2 C4 119.12(16) . . ?
O5 N2 C4 117.35(17) . . ?
O6 C8 C13 124.41(15) . . ?
O6 C8 C9 118.52(15) . . ?
C13 C8 C9 117.06(16) . . ?
C10 C9 C8 122.25(15) . . ?
C10 C9 N3A 115.0(9) . . ?
C8 C9 N3A 122.5(9) . . ?
C10 C9 N3B 118.0(12) . . ?
C8 C9 N3B 119.3(12) . . ?
N3A C9 N3B 11.5(16) . . ?
C11 C10 C9 118.37(16) . . ?
C11 C10 H7 120.8 . . ?
C9 C10 H7 120.8 . . ?
C10 C11 C12 121.65(16) . . ?
C10 C11 N4 118.73(15) . . ?
C12 C11 N4 119.61(15) . . ?
C13 C12 C11 119.49(16) . . ?
C13 C12 H8 120.3 . . ?
C11 C12 H8 120.3 . . ?
C12 C13 C8 121.16(16) . . ?
C12 C13 H9 119.4 . . ?
C8 C13 H9 119.4 . . ?
O6 C14 H10 109.5 . . ?
O6 C14 H11 109.5 . . ?
H10 C14 H11 109.5 . . ?
O6 C14 H12 109.5 . . ?
H10 C14 H12 109.5 . . ?
H11 C14 H12 109.5 . . ?
C8 O6 C14 118.34(15) . . ?
O8A N3A O7A 121.4(15) . . ?
O8A N3A C9 120.3(14) . . ?
O7A N3A C9 118.2(15) . . ?
O9 N4 O10 123.27(16) . . ?
O9 N4 C11 118.42(15) . . ?
O10 N4 C11 118.30(16) . . ?
O7B N3B O8B 125(2) . . ?
O7B N3B C9 122(2) . . ?
O8B N3B C9 112(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
O1 C1 C2 C3 -178.29(16) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
O1 C1 C2 N1 0.9(2) . . . . ?
C6 C1 C2 N1 179.83(16) . . . . ?
C1 C2 C3 C4 -2.1(3) . . . . ?
N1 C2 C3 C4 178.66(15) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C2 C3 C4 N2 -177.69(15) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
N2 C4 C5 C6 179.55(16) . . . . ?
C4 C5 C6 C1 -1.7(3) . . . . ?
O1 C1 C6 C5 -179.84(16) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
C6 C1 O1 C7 -12.2(3) . . . . ?
C2 C1 O1 C7 166.60(17) . . . . ?
C3 C2 N1 O3 33.0(2) . . . . ?
C1 C2 N1 O3 -146.29(18) . . . . ?
C3 C2 N1 O2 -146.10(17) . . . . ?
C1 C2 N1 O2 34.7(2) . . . . ?
C3 C4 N2 O4 -7.8(3) . . . . ?
C5 C4 N2 O4 172.77(17) . . . . ?
C3 C4 N2 O5 172.12(18) . . . . ?
C5 C4 N2 O5 -7.3(3) . . . . ?
O6 C8 C9 C10 179.59(16) . . . . ?
C13 C8 C9 C10 -0.5(3) . . . . ?
O6 C8 C9 N3A -5.8(9) . . . . ?
C13 C8 C9 N3A 174.1(8) . . . . ?
O6 C8 C9 N3B 7.1(12) . . . . ?
C13 C8 C9 N3B -173.0(12) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
N3A C9 C10 C11 -175.3(8) . . . . ?
N3B C9 C10 C11 172.3(12) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C9 C10 C11 N4 -178.85(15) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
N4 C11 C12 C13 179.26(16) . . . . ?
C11 C12 C13 C8 -0.6(3) . . . . ?
O6 C8 C13 C12 -179.18(17) . . . . ?
C9 C8 C13 C12 0.9(2) . . . . ?
C13 C8 O6 C14 -4.6(3) . . . . ?
C9 C8 O6 C14 175.29(16) . . . . ?
C10 C9 N3A O8A 28.2(19) . . . . ?
C8 C9 N3A O8A -146.8(13) . . . . ?
N3B C9 N3A O8A 136(12) . . . . ?
C10 C9 N3A O7A -156.8(12) . . . . ?
C8 C9 N3A O7A 28.2(19) . . . . ?
N3B C9 N3A O7A -49(10) . . . . ?
C10 C11 N4 O9 0.3(2) . . . . ?
C12 C11 N4 O9 -179.19(17) . . . . ?
C10 C11 N4 O10 179.51(16) . . . . ?
C12 C11 N4 O10 0.0(2) . . . . ?
C10 C9 N3B O7B 154(2) . . . . ?
C8 C9 N3B O7B -33(3) . . . . ?
N3A C9 N3B O7B 76(11) . . . . ?
C10 C9 N3B O8B -25(2) . . . . ?
C8 C9 N3B O8B 147.6(13) . . . . ?
N3A C9 N3B O8B -103(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.037
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24DNAN_a_243K
_database_code_depnum_ccdc_archive 'CCDC 1401655'
_audit_update_record             
;
2015-05-18 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.721(3)
_cell_length_b                   12.675(4)
_cell_length_c                   15.366(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.580(4)
_cell_angle_gamma                90.00
_cell_volume                     1683.7(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    243(2)
_cell_measurement_reflns_used    4014
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9707
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_process_details   
;CrystalClear (Rigaku Americas and Rigaku, 2009)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      243(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13438
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3841
_reflns_number_gt                2663
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0541P)²+0.2551P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3841
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.6961(2) 0.07476(14) 0.03044(11) 0.0397(4) Uani 1 1 d . . .
C2 C 0.8071(2) 0.02119(14) 0.08904(12) 0.0382(4) Uani 1 1 d . . .
C3 C 0.8499(2) 0.05488(15) 0.17378(12) 0.0398(4) Uani 1 1 d . . .
H1 H 0.9267 0.0193 0.2113 0.048 Uiso 1 1 calc R . .
C4 C 0.7768(2) 0.14223(15) 0.20212(12) 0.0404(4) Uani 1 1 d . . .
C5 C 0.6663(2) 0.19670(15) 0.14668(13) 0.0446(5) Uani 1 1 d . . .
H2 H 0.6175 0.2561 0.1673 0.053 Uiso 1 1 calc R . .
C6 C 0.6281(2) 0.16374(15) 0.06148(13) 0.0438(5) Uani 1 1 d . . .
H3 H 0.5549 0.2020 0.0236 0.053 Uiso 1 1 calc R . .
C7 C 0.5770(3) 0.10471(19) -0.11628(15) 0.0690(7) Uani 1 1 d . . .
H4 H 0.4732 0.1143 -0.1015 0.104 Uiso 1 1 calc R . .
H5 H 0.5718 0.0718 -0.1736 0.104 Uiso 1 1 calc R . .
H6 H 0.6276 0.1728 -0.1174 0.104 Uiso 1 1 calc R . .
O1 O 0.66396(17) 0.03820(11) -0.05151(8) 0.0543(4) Uani 1 1 d . . .
O2 O 0.8102(2) -0.13319(13) 0.00939(10) 0.0772(5) Uani 1 1 d . . .
O3 O 1.0167(2) -0.08835(14) 0.09274(13) 0.0815(6) Uani 1 1 d . . .
O4 O 0.92431(19) 0.13640(14) 0.33844(10) 0.0710(5) Uani 1 1 d . . .
O5 O 0.7376(2) 0.24812(16) 0.31819(11) 0.0886(6) Uani 1 1 d . . .
N1 N 0.8843(2) -0.07308(13) 0.06153(11) 0.0506(4) Uani 1 1 d . . .
N2 N 0.8164(2) 0.17770(15) 0.29252(12) 0.0548(5) Uani 1 1 d . . .
C8 C 0.7831(2) 0.42356(14) -0.13707(11) 0.0363(4) Uani 1 1 d . A .
C9 C 0.7308(2) 0.49612(14) -0.07855(12) 0.0383(4) Uani 1 1 d . . .
C10 C 0.7724(2) 0.48916(15) 0.01076(12) 0.0409(4) Uani 1 1 d . A .
H7 H 0.7351 0.5382 0.0488 0.049 Uiso 1 1 calc R . .
C11 C 0.8695(2) 0.40923(14) 0.04317(11) 0.0366(4) Uani 1 1 d . . .
C12 C 0.9232(2) 0.33573(14) -0.01171(13) 0.0433(5) Uani 1 1 d . A .
H8 H 0.9891 0.2811 0.0117 0.052 Uiso 1 1 calc R . .
C13 C 0.8799(2) 0.34293(14) -0.10072(13) 0.0430(5) Uani 1 1 d . . .
H9 H 0.9163 0.2925 -0.1379 0.052 Uiso 1 1 calc R A .
C14 C 0.7824(3) 0.35766(19) -0.28201(14) 0.0643(6) Uani 1 1 d . A .
H10 H 0.8943 0.3548 -0.2776 0.096 Uiso 1 1 calc R . .
H11 H 0.7396 0.3758 -0.3416 0.096 Uiso 1 1 calc R . .
H12 H 0.7432 0.2894 -0.2669 0.096 Uiso 1 1 calc R . .
O6 O 0.73806(15) 0.43611(11) -0.22265(8) 0.0492(4) Uani 1 1 d . . .
O7A O 0.6126(9) 0.6117(6) -0.1825(4) 0.0660(18) Uani 0.606(5) 1 d P A 1
O7B O 0.5637(17) 0.5901(10) -0.1770(9) 0.122(5) Uani 0.394(5) 1 d P A 2
O8A O 0.5271(4) 0.6044(3) -0.05894(19) 0.0736(13) Uani 0.606(5) 1 d P A 1
O8B O 0.6606(6) 0.6731(3) -0.0656(3) 0.080(2) Uani 0.394(5) 1 d P A 2
O9 O 0.8690(2) 0.46917(15) 0.18460(10) 0.0769(5) Uani 1 1 d . . .
O10 O 1.00391(19) 0.33155(12) 0.16575(10) 0.0657(4) Uani 1 1 d . . .
N3A N 0.6154(12) 0.5822(5) -0.1066(6) 0.0397(16) Uani 0.606(5) 1 d P A 1
N3B N 0.649(2) 0.5854(13) -0.1159(14) 0.075(5) Uani 0.394(5) 1 d P A 2
N4 N 0.91694(19) 0.40274(14) 0.13774(11) 0.0471(4) Uani 1 1 d . A .


_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 O1 1.336(2) . ?
C1 C6 1.388(3) . ?
C1 C2 1.407(2) . ?
C2 C3 1.374(3) . ?
C2 N1 1.461(2) . ?
C3 C4 1.376(3) . ?
C3 H1 0.9400 . ?
C4 C5 1.384(3) . ?
C4 N2 1.457(2) . ?
C5 C6 1.373(3) . ?
C5 H2 0.9400 . ?
C6 H3 0.9400 . ?
C7 O1 1.441(2) . ?
C7 H4 0.9700 . ?
C7 H5 0.9700 . ?
C7 H6 0.9700 . ?
O2 N1 1.226(2) . ?
O3 N1 1.206(2) . ?
O4 N2 1.217(2) . ?
O5 N2 1.223(2) . ?
C8 O6 1.331(2) . ?
C8 C13 1.395(2) . ?
C8 C9 1.404(2) . ?
C9 C10 1.375(2) . ?
C9 N3B 1.416(17) . ?
C9 N3A 1.508(7) . ?
C10 C11 1.371(2) . ?
C10 H7 0.9400 . ?
C11 C12 1.380(3) . ?
C11 N4 1.460(2) . ?
C12 C13 1.373(3) . ?
C12 H8 0.9400 . ?
C13 H9 0.9400 . ?
C14 O6 1.436(2) . ?
C14 H10 0.9700 . ?
C14 H11 0.9700 . ?
C14 H12 0.9700 . ?
O7A N3A 1.223(11) . ?
O7B N3B 1.12(2) . ?
O8A N3A 1.165(10) . ?
O8B N3B 1.350(18) . ?
O9 N4 1.217(2) . ?
O10 N4 1.220(2) . ?

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 C6 124.04(16) . . ?
O1 C1 C2 118.48(16) . . ?
C6 C1 C2 117.48(17) . . ?
C3 C2 C1 122.29(17) . . ?
C3 C2 N1 116.78(16) . . ?
C1 C2 N1 120.93(17) . . ?
C2 C3 C4 118.09(17) . . ?
C2 C3 H1 121.0 . . ?
C4 C3 H1 121.0 . . ?
C3 C4 C5 121.35(17) . . ?
C3 C4 N2 119.23(17) . . ?
C5 C4 N2 119.42(17) . . ?
C6 C5 C4 119.81(17) . . ?
C6 C5 H2 120.1 . . ?
C4 C5 H2 120.1 . . ?
C5 C6 C1 120.94(17) . . ?
C5 C6 H3 119.5 . . ?
C1 C6 H3 119.5 . . ?
O1 C7 H4 109.5 . . ?
O1 C7 H5 109.5 . . ?
H4 C7 H5 109.5 . . ?
O1 C7 H6 109.5 . . ?
H4 C7 H6 109.5 . . ?
H5 C7 H6 109.5 . . ?
C1 O1 C7 118.28(17) . . ?
O3 N1 O2 123.69(18) . . ?
O3 N1 C2 118.01(19) . . ?
O2 N1 C2 118.28(18) . . ?
O4 N2 O5 123.45(19) . . ?
O4 N2 C4 119.18(18) . . ?
O5 N2 C4 117.37(19) . . ?
O6 C8 C13 124.56(16) . . ?
O6 C8 C9 118.42(16) . . ?
C13 C8 C9 117.02(16) . . ?
C10 C9 C8 122.13(16) . . ?
C10 C9 N3B 120.5(8) . . ?
C8 C9 N3B 116.8(8) . . ?
C10 C9 N3A 114.2(4) . . ?
C8 C9 N3A 123.5(4) . . ?
N3B C9 N3A 13.2(11) . . ?
C11 C10 C9 118.63(17) . . ?
C11 C10 H7 120.7 . . ?
C9 C10 H7 120.7 . . ?
C10 C11 C12 121.35(17) . . ?
C10 C11 N4 118.93(16) . . ?
C12 C11 N4 119.73(16) . . ?
C13 C12 C11 119.54(17) . . ?
C13 C12 H8 120.2 . . ?
C11 C12 H8 120.2 . . ?
C12 C13 C8 121.34(17) . . ?
C12 C13 H9 119.3 . . ?
C8 C13 H9 119.3 . . ?
O6 C14 H10 109.5 . . ?
O6 C14 H11 109.5 . . ?
H10 C14 H11 109.5 . . ?
O6 C14 H12 109.5 . . ?
H10 C14 H12 109.5 . . ?
H11 C14 H12 109.5 . . ?
C8 O6 C14 118.39(16) . . ?
O8A N3A O7A 126.5(8) . . ?
O8A N3A C9 117.8(6) . . ?
O7A N3A C9 115.0(8) . . ?
O7B N3B O8B 115.1(15) . . ?
O7B N3B C9 128.7(16) . . ?
O8B N3B C9 115.6(14) . . ?
O9 N4 O10 123.30(17) . . ?
O9 N4 C11 118.39(16) . . ?
O10 N4 C11 118.31(17) . . ?

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 178.38(17) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
O1 C1 C2 N1 -0.8(3) . . . . ?
C6 C1 C2 N1 -179.91(16) . . . . ?
C1 C2 C3 C4 2.1(3) . . . . ?
N1 C2 C3 C4 -178.69(16) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C2 C3 C4 N2 178.09(16) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
N2 C4 C5 C6 -179.89(17) . . . . ?
C4 C5 C6 C1 1.6(3) . . . . ?
O1 C1 C6 C5 179.81(17) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C6 C1 O1 C7 12.3(3) . . . . ?
C2 C1 O1 C7 -166.70(18) . . . . ?
C3 C2 N1 O3 -32.6(3) . . . . ?
C1 C2 N1 O3 146.65(19) . . . . ?
C3 C2 N1 O2 146.07(18) . . . . ?
C1 C2 N1 O2 -34.7(2) . . . . ?
C3 C4 N2 O4 7.6(3) . . . . ?
C5 C4 N2 O4 -172.62(18) . . . . ?
C3 C4 N2 O5 -172.13(19) . . . . ?
C5 C4 N2 O5 7.6(3) . . . . ?
O6 C8 C9 C10 -179.67(17) . . . . ?
C13 C8 C9 C10 0.1(3) . . . . ?
O6 C8 C9 N3B -7.8(9) . . . . ?
C13 C8 C9 N3B 172.0(9) . . . . ?
O6 C8 C9 N3A 5.4(5) . . . . ?
C13 C8 C9 N3A -174.8(4) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
N3B C9 C10 C11 -170.9(9) . . . . ?
N3A C9 C10 C11 176.0(4) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C9 C10 C11 N4 178.64(16) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
N4 C11 C12 C13 -179.15(17) . . . . ?
C11 C12 C13 C8 0.3(3) . . . . ?
O6 C8 C13 C12 179.12(18) . . . . ?
C9 C8 C13 C12 -0.6(3) . . . . ?
C13 C8 O6 C14 4.7(3) . . . . ?
C9 C8 O6 C14 -175.58(17) . . . . ?
C10 C9 N3A O8A -30.7(9) . . . . ?
C8 C9 N3A O8A 144.6(6) . . . . ?
N3B C9 N3A O8A -152(6) . . . . ?
C10 C9 N3A O7A 158.3(7) . . . . ?
C8 C9 N3A O7A -26.4(10) . . . . ?
N3B C9 N3A O7A 37(5) . . . . ?
C10 C9 N3B O7B -150(2) . . . . ?
C8 C9 N3B O7B 38(3) . . . . ?
N3A C9 N3B O7B -85(5) . . . . ?
C10 C9 N3B O8B 20.7(18) . . . . ?
C8 C9 N3B O8B -151.3(10) . . . . ?
N3A C9 N3B O8B 85(5) . . . . ?
C10 C11 N4 O9 -0.4(3) . . . . ?
C12 C11 N4 O9 179.31(18) . . . . ?
C10 C11 N4 O10 -179.67(17) . . . . ?
C12 C11 N4 O10 0.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.036
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24DNAN_a_273K
_database_code_depnum_ccdc_archive 'CCDC 1401656'
_audit_update_record             
;
2015-05-18 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.767(3)
_cell_length_b                   12.675(4)
_cell_length_c                   15.411(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.912(5)
_cell_angle_gamma                90.00
_cell_volume                     1696.2(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3625
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9709
_exptl_absorpt_correction_T_max  0.9801
_exptl_absorpt_process_details   
;CrystalClear (Rigaku Americas and Rigaku, 2009)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13531
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3877
_reflns_number_gt                2459
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0705P)²+0.1269P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3877
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1466
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_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 0.1965(2) 0.07508(16) 0.53066(13) 0.0460(5) Uani 1 1 d . . .
C2 C 0.3066(2) 0.02186(15) 0.58948(13) 0.0443(5) Uani 1 1 d . . .
C3 C 0.3492(2) 0.05500(16) 0.67425(13) 0.0460(5) Uani 1 1 d . . .
H1 H 0.4251 0.0199 0.7115 0.055 Uiso 1 1 calc R . .
C4 C 0.2755(2) 0.14197(17) 0.70214(13) 0.0474(5) Uani 1 1 d . . .
C5 C 0.1650(2) 0.19645(17) 0.64678(15) 0.0527(6) Uani 1 1 d . . .
H2 H 0.1163 0.2548 0.6671 0.063 Uiso 1 1 calc R . .
C6 C 0.1281(2) 0.16355(16) 0.56154(15) 0.0516(5) Uani 1 1 d . . .
H3 H 0.0559 0.2013 0.5239 0.062 Uiso 1 1 calc R . .
C7 C 0.0769(3) 0.1050(2) 0.38396(17) 0.0815(9) Uani 1 1 d . . .
H4 H -0.0252 0.1141 0.3987 0.122 Uiso 1 1 calc R . .
H5 H 0.0713 0.0721 0.3275 0.122 Uiso 1 1 calc R . .
H6 H 0.1259 0.1725 0.3825 0.122 Uiso 1 1 calc R . .
O1 O 0.16506(19) 0.03918(12) 0.44892(9) 0.0637(5) Uani 1 1 d . . .
O2 O 0.3118(3) -0.13181(15) 0.50959(12) 0.0924(7) Uani 1 1 d . . .
O3 O 0.5157(2) -0.08752(15) 0.59386(15) 0.0965(7) Uani 1 1 d . . .
O4 O 0.4228(2) 0.13650(17) 0.83839(11) 0.0841(6) Uani 1 1 d . . .
O5 O 0.2364(3) 0.24720(19) 0.81823(13) 0.1045(7) Uani 1 1 d . . .
N1 N 0.3848(3) -0.07209(15) 0.56213(13) 0.0587(5) Uani 1 1 d . . .
N2 N 0.3152(3) 0.17728(17) 0.79274(13) 0.0644(5) Uani 1 1 d . . .
C8 C 0.2828(2) 0.42361(15) 0.36349(13) 0.0424(5) Uani 1 1 d . A .
C9 C 0.2312(2) 0.49603(15) 0.42190(13) 0.0437(5) Uani 1 1 d . . .
C10 C 0.2733(2) 0.48854(16) 0.51079(13) 0.0461(5) Uani 1 1 d . A .
H7 H 0.2371 0.5370 0.5484 0.055 Uiso 1 1 calc R . .
C11 C 0.3693(2) 0.40884(15) 0.54316(13) 0.0431(5) Uani 1 1 d . . .
C12 C 0.4229(2) 0.33546(16) 0.48849(15) 0.0511(5) Uani 1 1 d . A .
H8 H 0.4880 0.2815 0.5117 0.061 Uiso 1 1 calc R . .
C13 C 0.3795(2) 0.34265(16) 0.39953(14) 0.0500(5) Uani 1 1 d . . .
H9 H 0.4150 0.2929 0.3628 0.060 Uiso 1 1 calc R A .
C14 C 0.2807(3) 0.3583(2) 0.21831(16) 0.0758(8) Uani 1 1 d . A .
H10 H 0.3909 0.3559 0.2224 0.114 Uiso 1 1 calc R . .
H11 H 0.2373 0.3764 0.1596 0.114 Uiso 1 1 calc R . .
H12 H 0.2429 0.2904 0.2331 0.114 Uiso 1 1 calc R . .
O6 O 0.23719(18) 0.43623(12) 0.27796(9) 0.0578(4) Uani 1 1 d . . .
O7A O 0.1151(11) 0.6110(7) 0.3177(5) 0.078(2) Uani 0.592(6) 1 d P A 1
O7B O 0.0608(19) 0.5906(11) 0.3258(10) 0.139(6) Uani 0.408(6) 1 d P A 2
O8A O 0.0280(5) 0.6036(3) 0.4408(2) 0.0839(17) Uani 0.592(6) 1 d P A 1
O8B O 0.1609(7) 0.6724(4) 0.4341(3) 0.092(3) Uani 0.408(6) 1 d P A 2
N3B N 0.151(3) 0.5885(18) 0.3843(18) 0.077(6) Uani 0.408(6) 1 d P A 2
N3A N 0.1161(15) 0.5809(8) 0.3940(10) 0.046(2) Uani 0.592(6) 1 d P A 1
O9 O 0.3696(2) 0.46844(18) 0.68452(11) 0.0899(7) Uani 1 1 d . . .
O10 O 0.5034(2) 0.33090(14) 0.66553(11) 0.0776(5) Uani 1 1 d . . .
N4 N 0.4168(2) 0.40211(16) 0.63768(12) 0.0555(5) Uani 1 1 d . A .


_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 O1 1.332(2) . ?
C1 C6 1.386(3) . ?
C1 C2 1.403(3) . ?
C2 C3 1.374(3) . ?
C2 N1 1.465(3) . ?
C3 C4 1.376(3) . ?
C3 H1 0.9300 . ?
C4 C5 1.384(3) . ?
C4 N2 1.462(3) . ?
C5 C6 1.374(3) . ?
C5 H2 0.9300 . ?
C6 H3 0.9300 . ?
C7 O1 1.443(3) . ?
C7 H4 0.9600 . ?
C7 H5 0.9600 . ?
C7 H6 0.9600 . ?
O2 N1 1.223(3) . ?
O3 N1 1.200(3) . ?
O4 N2 1.212(3) . ?
O5 N2 1.222(3) . ?
C8 O6 1.333(2) . ?
C8 C13 1.397(3) . ?
C8 C9 1.403(3) . ?
C9 C10 1.372(3) . ?
C9 N3B 1.44(2) . ?
C9 N3A 1.497(10) . ?
C10 C11 1.365(3) . ?
C10 H7 0.9300 . ?
C11 C12 1.380(3) . ?
C11 N4 1.461(3) . ?
C12 C13 1.374(3) . ?
C12 H8 0.9300 . ?
C13 H9 0.9300 . ?
C14 O6 1.436(3) . ?
C14 H10 0.9600 . ?
C14 H11 0.9600 . ?
C14 H12 0.9600 . ?
O7A N3A 1.235(17) . ?
O7B N3B 1.12(3) . ?
O8A N3A 1.164(14) . ?
O8B N3B 1.31(3) . ?
O9 N4 1.217(2) . ?
O10 N4 1.218(2) . ?

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 C6 123.92(19) . . ?
O1 C1 C2 118.76(18) . . ?
C6 C1 C2 117.31(19) . . ?
C3 C2 C1 122.70(18) . . ?
C3 C2 N1 116.44(19) . . ?
C1 C2 N1 120.85(19) . . ?
C2 C3 C4 117.64(19) . . ?
C2 C3 H1 121.2 . . ?
C4 C3 H1 121.2 . . ?
C3 C4 C5 121.7(2) . . ?
C3 C4 N2 118.9(2) . . ?
C5 C4 N2 119.4(2) . . ?
C6 C5 C4 119.4(2) . . ?
C6 C5 H2 120.3 . . ?
C4 C5 H2 120.3 . . ?
C5 C6 C1 121.16(19) . . ?
C5 C6 H3 119.4 . . ?
C1 C6 H3 119.4 . . ?
O1 C7 H4 109.5 . . ?
O1 C7 H5 109.5 . . ?
H4 C7 H5 109.5 . . ?
O1 C7 H6 109.5 . . ?
H4 C7 H6 109.5 . . ?
H5 C7 H6 109.5 . . ?
C1 O1 C7 118.68(19) . . ?
O3 N1 O2 123.6(2) . . ?
O3 N1 C2 118.3(2) . . ?
O2 N1 C2 118.1(2) . . ?
O4 N2 O5 123.5(2) . . ?
O4 N2 C4 119.2(2) . . ?
O5 N2 C4 117.3(2) . . ?
O6 C8 C13 124.34(18) . . ?
O6 C8 C9 118.46(18) . . ?
C13 C8 C9 117.20(18) . . ?
C10 C9 C8 121.94(18) . . ?
C10 C9 N3B 120.4(11) . . ?
C8 C9 N3B 117.0(11) . . ?
C10 C9 N3A 114.5(6) . . ?
C8 C9 N3A 123.3(6) . . ?
N3B C9 N3A 14.5(13) . . ?
C11 C10 C9 118.94(19) . . ?
C11 C10 H7 120.5 . . ?
C9 C10 H7 120.5 . . ?
C10 C11 C12 121.36(19) . . ?
C10 C11 N4 118.97(18) . . ?
C12 C11 N4 119.66(18) . . ?
C13 C12 C11 119.56(19) . . ?
C13 C12 H8 120.2 . . ?
C11 C12 H8 120.2 . . ?
C12 C13 C8 121.00(19) . . ?
C12 C13 H9 119.5 . . ?
C8 C13 H9 119.5 . . ?
O6 C14 H10 109.5 . . ?
O6 C14 H11 109.5 . . ?
H10 C14 H11 109.5 . . ?
O6 C14 H12 109.5 . . ?
H10 C14 H12 109.5 . . ?
H11 C14 H12 109.5 . . ?
C8 O6 C14 118.70(18) . . ?
O7B N3B O8B 115.8(19) . . ?
O7B N3B C9 126(2) . . ?
O8B N3B C9 116(2) . . ?
O8A N3A O7A 126.6(10) . . ?
O8A N3A C9 118.5(10) . . ?
O7A N3A C9 114.4(10) . . ?
O9 N4 O10 123.3(2) . . ?
O9 N4 C11 118.50(18) . . ?
O10 N4 C11 118.2(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
O1 C1 C2 C3 178.17(19) . . . . ?
C6 C1 C2 C3 -1.0(3) . . . . ?
O1 C1 C2 N1 -0.6(3) . . . . ?
C6 C1 C2 N1 -179.77(19) . . . . ?
C1 C2 C3 C4 2.3(3) . . . . ?
N1 C2 C3 C4 -178.86(18) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C2 C3 C4 N2 178.26(19) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
N2 C4 C5 C6 179.76(19) . . . . ?
C4 C5 C6 C1 1.8(3) . . . . ?
O1 C1 C6 C5 179.8(2) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C6 C1 O1 C7 11.7(3) . . . . ?
C2 C1 O1 C7 -167.4(2) . . . . ?
C3 C2 N1 O3 -32.0(3) . . . . ?
C1 C2 N1 O3 146.9(2) . . . . ?
C3 C2 N1 O2 146.4(2) . . . . ?
C1 C2 N1 O2 -34.8(3) . . . . ?
C3 C4 N2 O4 7.7(3) . . . . ?
C5 C4 N2 O4 -172.4(2) . . . . ?
C3 C4 N2 O5 -172.2(2) . . . . ?
C5 C4 N2 O5 7.7(3) . . . . ?
O6 C8 C9 C10 -179.82(19) . . . . ?
C13 C8 C9 C10 0.1(3) . . . . ?
O6 C8 C9 N3B -9.3(11) . . . . ?
C13 C8 C9 N3B 170.6(11) . . . . ?
O6 C8 C9 N3A 5.9(6) . . . . ?
C13 C8 C9 N3A -174.3(6) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
N3B C9 C10 C11 -169.7(11) . . . . ?
N3A C9 C10 C11 175.4(6) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C9 C10 C11 N4 178.72(18) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
N4 C11 C12 C13 -179.25(19) . . . . ?
C11 C12 C13 C8 0.5(3) . . . . ?
O6 C8 C13 C12 179.3(2) . . . . ?
C9 C8 C13 C12 -0.6(3) . . . . ?
C13 C8 O6 C14 4.4(3) . . . . ?
C9 C8 O6 C14 -175.70(19) . . . . ?
C10 C9 N3B O7B -145(2) . . . . ?
C8 C9 N3B O7B 44(3) . . . . ?
N3A C9 N3B O7B -76(7) . . . . ?
C10 C9 N3B O8B 18(2) . . . . ?
C8 C9 N3B O8B -152.4(13) . . . . ?
N3A C9 N3B O8B 88(7) . . . . ?
C10 C9 N3A O8A -30.3(14) . . . . ?
C8 C9 N3A O8A 144.4(9) . . . . ?
N3B C9 N3A O8A -147(8) . . . . ?
C10 C9 N3A O7A 157.6(9) . . . . ?
C8 C9 N3A O7A -27.7(14) . . . . ?
N3B C9 N3A O7A 41(6) . . . . ?
C10 C11 N4 O9 -0.4(3) . . . . ?
C12 C11 N4 O9 179.1(2) . . . . ?
C10 C11 N4 O10 -179.5(2) . . . . ?
C12 C11 N4 O10 0.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.108
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24DNAN_a_298K
_database_code_depnum_ccdc_archive 'CCDC 1401657'
_audit_update_record             
;
2015-05-18 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          369.8
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.794(3)
_cell_length_b                   12.678(3)
_cell_length_c                   15.437(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.052(4)
_cell_angle_gamma                90.00
_cell_volume                     1704.1(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3515
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9711
_exptl_absorpt_correction_T_max  0.9801
_exptl_absorpt_process_details   
;CrystalClear (Rigaku Americas and Rigaku, 2009)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13575
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3895
_reflns_number_gt                2415
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0605P)²+0.2313P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3895
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1483
_refine_ls_wR_factor_gt          0.1274
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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 0.6962(2) 0.42473(17) 0.53088(14) 0.0507(5) Uani 1 1 d . . .
C2 C 0.8066(2) 0.47772(16) 0.58975(14) 0.0481(5) Uani 1 1 d . . .
C3 C 0.8482(2) 0.44468(18) 0.67437(14) 0.0517(6) Uani 1 1 d . . .
H1 H 0.9238 0.4798 0.7117 0.062 Uiso 1 1 calc R . .
C4 C 0.7748(3) 0.35813(18) 0.70225(15) 0.0522(6) Uani 1 1 d . . .
C5 C 0.6644(3) 0.30420(18) 0.64701(17) 0.0582(6) Uani 1 1 d . . .
H2 H 0.6155 0.2461 0.6674 0.070 Uiso 1 1 calc R . .
C6 C 0.6274(2) 0.33656(18) 0.56215(16) 0.0572(6) Uani 1 1 d . . .
H3 H 0.5549 0.2989 0.5247 0.069 Uiso 1 1 calc R . .
C7 C 0.5775(4) 0.3950(2) 0.38405(19) 0.0908(10) Uani 1 1 d . . .
H4 H 0.6258 0.3272 0.3829 0.136 Uiso 1 1 calc R . .
H5 H 0.5729 0.4278 0.3277 0.136 Uiso 1 1 calc R . .
H6 H 0.4754 0.3864 0.3983 0.136 Uiso 1 1 calc R . .
O1 O 0.6654(2) 0.46037(14) 0.44912(10) 0.0708(5) Uani 1 1 d . . .
O2 O 0.8120(3) 0.63112(17) 0.50958(13) 0.1017(8) Uani 1 1 d . . .
O3 O 1.0143(3) 0.58730(17) 0.59464(17) 0.1067(8) Uani 1 1 d . . .
O4 O 0.9220(3) 0.36361(19) 0.83839(13) 0.0933(7) Uani 1 1 d . . .
O5 O 0.7353(3) 0.2534(2) 0.81826(14) 0.1161(8) Uani 1 1 d . . .
N1 N 0.8844(3) 0.57155(16) 0.56237(14) 0.0648(6) Uani 1 1 d . . .
N2 N 0.8143(3) 0.32282(19) 0.79280(15) 0.0705(6) Uani 1 1 d . . .
C8 C 0.7825(2) 0.07651(16) 0.36369(14) 0.0459(5) Uani 1 1 d . . .
C9 C 0.7318(2) 0.00425(16) 0.42221(14) 0.0474(5) Uani 1 1 d . A .
C10 C 0.7739(2) 0.01182(17) 0.51085(14) 0.0511(5) Uani 1 1 d . . .
H7 H 0.7378 -0.0366 0.5484 0.061 Uiso 1 1 calc R . .
C11 C 0.8696(2) 0.09162(17) 0.54327(13) 0.0470(5) Uani 1 1 d . . .
C12 C 0.9225(3) 0.16460(17) 0.48861(16) 0.0553(6) Uani 1 1 d . . .
H8 H 0.9876 0.2186 0.5117 0.066 Uiso 1 1 calc R . .
C13 C 0.8790(3) 0.15743(17) 0.39990(15) 0.0552(6) Uani 1 1 d . . .
H9 H 0.9143 0.2073 0.3633 0.066 Uiso 1 1 calc R . .
C14 C 0.7800(3) 0.1413(2) 0.21876(17) 0.0827(9) Uani 1 1 d . . .
H10 H 0.7388 0.2086 0.2318 0.124 Uiso 1 1 calc R . .
H11 H 0.7402 0.1214 0.1600 0.124 Uiso 1 1 calc R . .
H12 H 0.8900 0.1458 0.2245 0.124 Uiso 1 1 calc R . .
O6 O 0.73706(19) 0.06369(13) 0.27853(10) 0.0637(5) Uani 1 1 d . . .
O7A O 0.6181(10) -0.1126(7) 0.3198(5) 0.095(3) Uani 0.587(7) 1 d P A 1
O7B O 0.5672(17) -0.0918(10) 0.3246(7) 0.144(6) Uani 0.413(7) 1 d P A 2
O8B O 0.6621(8) -0.1722(4) 0.4341(4) 0.102(3) Uani 0.413(7) 1 d P A 2
O8A O 0.5288(5) -0.1032(4) 0.4410(2) 0.094(2) Uani 0.587(7) 1 d P A 1
O9 O 0.8704(3) 0.03245(19) 0.68423(12) 0.0987(7) Uani 1 1 d . . .
O10 O 1.0033(2) 0.16975(16) 0.66557(12) 0.0879(6) Uani 1 1 d . . .
N3 N 0.6280(3) -0.08234(18) 0.39144(16) 0.0725(6) Uani 1 1 d . . .
N4 N 0.9171(2) 0.09858(18) 0.63754(13) 0.0620(5) 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
C1 O1 1.332(3) . ?
C1 C6 1.389(3) . ?
C1 C2 1.404(3) . ?
C2 C3 1.372(3) . ?
C2 N1 1.464(3) . ?
C3 C4 1.373(3) . ?
C3 H1 0.9300 . ?
C4 C5 1.380(3) . ?
C4 N2 1.462(3) . ?
C5 C6 1.368(3) . ?
C5 H2 0.9300 . ?
C6 H3 0.9300 . ?
C7 O1 1.441(3) . ?
C7 H4 0.9600 . ?
C7 H5 0.9600 . ?
C7 H6 0.9600 . ?
O2 N1 1.222(3) . ?
O3 N1 1.198(3) . ?
O4 N2 1.214(3) . ?
O5 N2 1.219(3) . ?
C8 O6 1.330(2) . ?
C8 C13 1.397(3) . ?
C8 C9 1.403(3) . ?
C9 C10 1.370(3) . ?
C9 N3 1.464(3) . ?
C10 C11 1.366(3) . ?
C10 H7 0.9300 . ?
C11 C12 1.376(3) . ?
C11 N4 1.459(3) . ?
C12 C13 1.372(3) . ?
C12 H8 0.9300 . ?
C13 H9 0.9300 . ?
C14 O6 1.435(3) . ?
C14 H10 0.9600 . ?
C14 H11 0.9600 . ?
C14 H12 0.9600 . ?
O7A N3 1.163(7) . ?
O7B N3 1.100(10) . ?
O8B N3 1.329(5) . ?
O8A N3 1.266(4) . ?
O9 N4 1.214(3) . ?
O10 N4 1.218(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 C6 124.1(2) . . ?
O1 C1 C2 118.8(2) . . ?
C6 C1 C2 117.1(2) . . ?
C3 C2 C1 122.6(2) . . ?
C3 C2 N1 116.7(2) . . ?
C1 C2 N1 120.7(2) . . ?
C2 C3 C4 117.9(2) . . ?
C2 C3 H1 121.0 . . ?
C4 C3 H1 121.0 . . ?
C3 C4 C5 121.6(2) . . ?
C3 C4 N2 119.0(2) . . ?
C5 C4 N2 119.4(2) . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H2 120.1 . . ?
C4 C5 H2 120.1 . . ?
C5 C6 C1 121.1(2) . . ?
C5 C6 H3 119.4 . . ?
C1 C6 H3 119.4 . . ?
O1 C7 H4 109.5 . . ?
O1 C7 H5 109.5 . . ?
H4 C7 H5 109.5 . . ?
O1 C7 H6 109.5 . . ?
H4 C7 H6 109.5 . . ?
H5 C7 H6 109.5 . . ?
C1 O1 C7 118.9(2) . . ?
O3 N1 O2 123.5(2) . . ?
O3 N1 C2 118.2(2) . . ?
O2 N1 C2 118.3(2) . . ?
O4 N2 O5 123.6(2) . . ?
O4 N2 C4 119.0(2) . . ?
O5 N2 C4 117.4(2) . . ?
O6 C8 C13 124.54(19) . . ?
O6 C8 C9 118.58(19) . . ?
C13 C8 C9 116.88(19) . . ?
C10 C9 C8 122.13(19) . . ?
C10 C9 N3 116.46(19) . . ?
C8 C9 N3 121.40(19) . . ?
C11 C10 C9 119.0(2) . . ?
C11 C10 H7 120.5 . . ?
C9 C10 H7 120.5 . . ?
C10 C11 C12 121.2(2) . . ?
C10 C11 N4 119.1(2) . . ?
C12 C11 N4 119.8(2) . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H8 120.1 . . ?
C11 C12 H8 120.1 . . ?
C12 C13 C8 121.1(2) . . ?
C12 C13 H9 119.4 . . ?
C8 C13 H9 119.4 . . ?
O6 C14 H10 109.5 . . ?
O6 C14 H11 109.5 . . ?
H10 C14 H11 109.5 . . ?
O6 C14 H12 109.5 . . ?
H10 C14 H12 109.5 . . ?
H11 C14 H12 109.5 . . ?
C8 O6 C14 118.82(19) . . ?
O7B N3 O7A 27.1(10) . . ?
O7B N3 O8A 105.0(9) . . ?
O7A N3 O8A 122.7(5) . . ?
O7B N3 O8B 114.7(7) . . ?
O7A N3 O8B 99.8(6) . . ?
O8A N3 O8B 69.4(3) . . ?
O7B N3 C9 125.8(7) . . ?
O7A N3 C9 121.1(5) . . ?
O8A N3 C9 114.3(3) . . ?
O8B N3 C9 113.3(3) . . ?
O9 N4 O10 123.1(2) . . ?
O9 N4 C11 118.5(2) . . ?
O10 N4 C11 118.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -178.2(2) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
O1 C1 C2 N1 1.2(3) . . . . ?
C6 C1 C2 N1 -179.8(2) . . . . ?
C1 C2 C3 C4 -1.9(3) . . . . ?
N1 C2 C3 C4 178.70(19) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C2 C3 C4 N2 -178.5(2) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
N2 C4 C5 C6 -179.8(2) . . . . ?
C4 C5 C6 C1 -1.7(3) . . . . ?
O1 C1 C6 C5 180.0(2) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C6 C1 O1 C7 -11.8(3) . . . . ?
C2 C1 O1 C7 167.2(2) . . . . ?
C3 C2 N1 O3 31.7(3) . . . . ?
C1 C2 N1 O3 -147.7(2) . . . . ?
C3 C2 N1 O2 -146.4(2) . . . . ?
C1 C2 N1 O2 34.2(3) . . . . ?
C3 C4 N2 O4 -7.8(3) . . . . ?
C5 C4 N2 O4 172.5(2) . . . . ?
C3 C4 N2 O5 171.9(2) . . . . ?
C5 C4 N2 O5 -7.7(3) . . . . ?
O6 C8 C9 C10 179.8(2) . . . . ?
C13 C8 C9 C10 0.1(3) . . . . ?
O6 C8 C9 N3 -1.5(3) . . . . ?
C13 C8 C9 N3 178.8(2) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
N3 C9 C10 C11 -179.5(2) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C9 C10 C11 N4 -178.77(19) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
N4 C11 C12 C13 179.4(2) . . . . ?
C11 C12 C13 C8 -0.6(3) . . . . ?
O6 C8 C13 C12 -179.1(2) . . . . ?
C9 C8 C13 C12 0.6(3) . . . . ?
C13 C8 O6 C14 -4.4(3) . . . . ?
C9 C8 O6 C14 175.8(2) . . . . ?
C10 C9 N3 O7B 168.6(11) . . . . ?
C8 C9 N3 O7B -10.2(12) . . . . ?
C10 C9 N3 O7A -159.3(6) . . . . ?
C8 C9 N3 O7A 21.9(6) . . . . ?
C10 C9 N3 O8A 36.0(4) . . . . ?
C8 C9 N3 O8A -142.8(3) . . . . ?
C10 C9 N3 O8B -40.9(5) . . . . ?
C8 C9 N3 O8B 140.3(4) . . . . ?
C10 C11 N4 O9 0.5(3) . . . . ?
C12 C11 N4 O9 -179.1(2) . . . . ?
C10 C11 N4 O10 179.6(2) . . . . ?
C12 C11 N4 O10 0.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.032
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
