# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
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data_mo_20140917campna2_0m
_database_code_depnum_ccdc_archive 'CCDC 1026499'
_audit_update_record             
;
2014-09-29 deposited with the CCDC.
2016-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        "ADENOSINE-3',5'-CYCLIC PHOSPHATE SODIUM"
_chemical_name_common            
"cAMPNa ;  CYCLIC AMP SODIUM SALT;3',5'-CYCLIC AMP SODIUM SALT"
_chemical_melting_point          ?
_chemical_formula_moiety         'C10H11N5O6PNa (5 H2O)'
_chemical_formula_sum            'C10 H21 N5 Na O11 P'
_chemical_formula_weight         441.28
_chemical_absolute_configuration ad

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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '

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

_cell_length_a                   6.5585(12)
_cell_length_b                   7.0470(13)
_cell_length_c                   38.869(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1796.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7116
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      27.43

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9385
_exptl_absorpt_correction_T_max  0.9476
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12569
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         1.05
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3174
_reflns_number_gt                3059
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of 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)+(0.0757P)²+1.6134P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.08(18)
_refine_ls_number_reflns         3174
_refine_ls_number_parameters     254
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.1381
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.148
_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 0.6996(5) 1.4051(5) 1.01681(9) 0.0229(7) Uani 1 1 d . . .
C2 C 0.7007(6) 1.0951(6) 1.03578(9) 0.0253(8) Uani 1 1 d . . .
H2 H 0.6970 1.0144 1.0547 0.030 Uiso 1 1 calc R . .
C3 C 0.7084(5) 1.1376(5) 0.97988(9) 0.0200(7) Uani 1 1 d . . .
C4 C 0.7037(6) 1.2767(5) 0.92918(9) 0.0260(8) Uani 1 1 d . . .
H4 H 0.7034 1.2923 0.9054 0.031 Uiso 1 1 calc RD . .
C5 C 0.7000(5) 1.3329(5) 0.98314(9) 0.0228(7) Uani 1 1 d . . .
C6 C 0.7315(6) 0.9171(5) 0.92951(8) 0.0233(7) Uani 1 1 d . . .
H6 H 0.7316 0.8229 0.9481 0.028 Uiso 1 1 calc R . .
C7 C 0.5615(6) 0.8612(5) 0.90324(9) 0.0214(7) Uani 1 1 d . . .
H7 H 0.4677 0.9681 0.9002 0.026 Uiso 1 1 calc R . .
C8 C 0.6884(5) 0.8349(5) 0.87067(8) 0.0200(7) Uani 1 1 d . . .
H8 H 0.7054 0.9580 0.8593 0.024 Uiso 1 1 calc R . .
C9 C 0.8922(6) 0.7706(6) 0.88491(9) 0.0242(8) Uani 1 1 d . . .
H9 H 0.8797 0.6427 0.8946 0.029 Uiso 1 1 calc R . .
C10 C 1.0554(6) 0.7734(6) 0.85763(9) 0.0297(9) Uani 1 1 d . . .
H10A H 1.0766 0.9015 0.8493 0.036 Uiso 1 1 calc RD . .
H10B H 1.1832 0.7261 0.8668 0.036 Uiso 1 1 calc RD . .
N1 N 0.7004(6) 1.5899(5) 1.02435(8) 0.0308(7) Uani 1 1 d . . .
H1A H 0.6475 1.6068 1.0452 0.046 Uiso 1 1 d R . .
H1C H 0.8281 1.6326 1.0241 0.046 Uiso 1 1 d R . .
N2 N 0.6973(5) 1.2795(5) 1.04309(7) 0.0259(7) Uani 1 1 d . . .
N3 N 0.7087(5) 1.0092(4) 1.00517(7) 0.0235(7) Uani 1 1 d . . .
N4 N 0.7123(5) 1.1026(4) 0.94477(7) 0.0231(6) Uani 1 1 d . . .
N5 N 0.6962(5) 1.4173(4) 0.95050(7) 0.0246(7) Uani 1 1 d . . .
Na1 Na 0.4908(3) 0.4285(3) 0.74937(4) 0.0382(4) Uani 1 1 d . . .
O1 O 0.9236(4) 0.9058(4) 0.91197(6) 0.0284(6) Uani 1 1 d . . .
O2 O 0.4510(4) 0.6995(4) 0.91381(7) 0.0329(6) Uani 1 1 d . . .
H2A H 0.5283 0.6249 0.9234 0.049 Uiso 1 1 calc R . .
O3 O 0.6133(4) 0.7003(4) 0.84635(6) 0.0261(6) Uani 1 1 d . . .
O4 O 0.9837(4) 0.6519(4) 0.83014(6) 0.0310(6) Uani 1 1 d . . .
O5 O 0.7567(5) 0.8612(4) 0.79341(7) 0.0366(7) Uani 1 1 d . . .
O6 O 0.7081(5) 0.5025(4) 0.79583(7) 0.0384(7) Uani 1 1 d . . .
O7 O 0.5121(6) 0.2738(5) 0.85238(8) 0.0554(9) Uani 1 1 d D . .
H7B H 0.5054 0.3853 0.8432 0.066 Uiso 1 1 d RD . .
H7A H 0.4573 0.2495 0.8716 0.066 Uiso 1 1 d RD . .
O8 O 0.1281(8) 0.2911(7) 0.88104(10) 0.0739(13) Uani 1 1 d D . .
H8B H 0.1505 0.2143 0.8973 0.089 Uiso 1 1 d RD . .
H8A H 0.1977 0.3892 0.8765 0.089 Uiso 1 1 d RD . .
O9 O 0.2594(6) 0.6826(6) 0.76842(8) 0.0549(9) Uani 1 1 d D . .
H9A H 0.2147 0.6576 0.7884 0.066 Uiso 1 1 d RD . .
H9B H 0.1446 0.6990 0.7622 0.066 Uiso 1 1 d RD . .
O10 O 0.6309(5) 0.6727(5) 0.71482(8) 0.0441(8) Uani 1 1 d . . .
H10C H 0.7351 0.6729 0.7104 0.053 Uiso 1 1 d R . .
H10D H 0.5898 0.6841 0.6967 0.053 Uiso 1 1 d R . .
O11 O 0.0405(6) 0.6893(5) 0.69205(13) 0.0741(13) Uani 1 1 d D . .
H11A H 0.1215 0.8119 0.6930 0.089 Uiso 1 1 d RD . .
H11B H 0.0416 0.6639 0.7127 0.089 Uiso 1 1 d RD . .
P1 P 0.76124(15) 0.68252(14) 0.81314(2) 0.0253(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 N1 1.335(5) . ?
C1 N2 1.352(5) . ?
C1 C5 1.404(5) . ?
C2 N2 1.331(5) . ?
C2 N3 1.336(5) . ?
C2 H2 0.9300 . ?
C3 N3 1.336(4) . ?
C3 C5 1.383(5) . ?
C3 N4 1.387(4) . ?
C4 N5 1.293(5) . ?
C4 N4 1.370(5) . ?
C4 H4 0.9300 . ?
C5 N5 1.402(4) . ?
C6 O1 1.435(5) . ?
C6 N4 1.441(4) . ?
C6 C7 1.562(5) . ?
C6 H6 0.9800 . ?
C7 O2 1.411(4) . ?
C7 C8 1.526(5) . ?
C7 H7 0.9800 . ?
C8 O3 1.427(4) . ?
C8 C9 1.516(5) . ?
C8 H8 0.9800 . ?
C9 O1 1.434(4) . ?
C9 C10 1.507(5) . ?
C9 H9 0.9800 . ?
C10 O4 1.448(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N1 H1A 0.8900 . ?
N1 H1C 0.8900 . ?
Na1 O6 2.359(3) . ?
Na1 O10 2.368(4) . ?
Na1 O5 2.372(3) 3_646 ?
Na1 O10 2.413(4) 3_646 ?
Na1 O9 2.461(4) . ?
Na1 O9 2.483(4) 3_646 ?
Na1 P1 3.412(2) 3_646 ?
Na1 Na1 3.5259(7) 3_656 ?
Na1 Na1 3.5259(7) 3_646 ?
O2 H2A 0.8200 . ?
O3 P1 1.620(3) . ?
O4 P1 1.616(3) . ?
O5 P1 1.475(3) . ?
O5 Na1 2.372(3) 3_656 ?
O6 P1 1.477(3) . ?
O7 H7B 0.8644 . ?
O7 H7A 0.8469 . ?
O8 H8B 0.8454 . ?
O8 H8A 0.8473 . ?
O9 Na1 2.483(4) 3_656 ?
O9 H9A 0.8482 . ?
O9 H9B 0.7990 . ?
O10 Na1 2.413(4) 3_656 ?
O10 H10C 0.7052 . ?
O10 H10D 0.7602 . ?
O11 H11A 1.0152 . ?
O11 H11B 0.8211 . ?
P1 Na1 3.412(2) 3_656 ?

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
N1 C1 N2 118.2(3) . . ?
N1 C1 C5 124.0(3) . . ?
N2 C1 C5 117.8(3) . . ?
N2 C2 N3 129.3(3) . . ?
N2 C2 H2 115.4 . . ?
N3 C2 H2 115.4 . . ?
N3 C3 C5 127.3(3) . . ?
N3 C3 N4 127.1(3) . . ?
C5 C3 N4 105.5(3) . . ?
N5 C4 N4 113.9(3) . . ?
N5 C4 H4 123.1 . . ?
N4 C4 H4 123.1 . . ?
C3 C5 N5 109.9(3) . . ?
C3 C5 C1 116.5(3) . . ?
N5 C5 C1 133.6(4) . . ?
O1 C6 N4 108.8(3) . . ?
O1 C6 C7 107.6(3) . . ?
N4 C6 C7 115.8(3) . . ?
O1 C6 H6 108.1 . . ?
N4 C6 H6 108.1 . . ?
C7 C6 H6 108.1 . . ?
O2 C7 C8 115.1(3) . . ?
O2 C7 C6 112.3(3) . . ?
C8 C7 C6 100.6(3) . . ?
O2 C7 H7 109.5 . . ?
C8 C7 H7 109.5 . . ?
C6 C7 H7 109.5 . . ?
O3 C8 C9 110.3(3) . . ?
O3 C8 C7 116.2(3) . . ?
C9 C8 C7 102.4(3) . . ?
O3 C8 H8 109.2 . . ?
C9 C8 H8 109.2 . . ?
C7 C8 H8 109.2 . . ?
O1 C9 C10 113.9(3) . . ?
O1 C9 C8 101.3(3) . . ?
C10 C9 C8 111.5(3) . . ?
O1 C9 H9 110.0 . . ?
C10 C9 H9 110.0 . . ?
C8 C9 H9 110.0 . . ?
O4 C10 C9 106.3(3) . . ?
O4 C10 H10A 110.5 . . ?
C9 C10 H10A 110.5 . . ?
O4 C10 H10B 110.5 . . ?
C9 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
C1 N1 H1A 109.2 . . ?
C1 N1 H1C 109.3 . . ?
H1A N1 H1C 109.5 . . ?
C2 N2 C1 118.6(3) . . ?
C3 N3 C2 110.4(3) . . ?
C4 N4 C3 106.0(3) . . ?
C4 N4 C6 129.4(3) . . ?
C3 N4 C6 124.6(3) . . ?
C4 N5 C5 104.7(3) . . ?
O6 Na1 O10 92.23(13) . . ?
O6 Na1 O5 173.97(15) . 3_646 ?
O10 Na1 O5 90.77(12) . 3_646 ?
O6 Na1 O10 85.62(12) . 3_646 ?
O10 Na1 O10 176.48(12) . 3_646 ?
O5 Na1 O10 91.63(12) 3_646 3_646 ?
O6 Na1 O9 88.93(13) . . ?
O10 Na1 O9 83.18(13) . . ?
O5 Na1 O9 86.23(13) 3_646 . ?
O10 Na1 O9 99.55(13) 3_646 . ?
O6 Na1 O9 88.22(13) . 3_646 ?
O10 Na1 O9 95.35(13) . 3_646 ?
O5 Na1 O9 96.71(12) 3_646 3_646 ?
O10 Na1 O9 81.81(13) 3_646 3_646 ?
O9 Na1 O9 176.74(13) . 3_646 ?
O6 Na1 P1 161.86(11) . 3_646 ?
O10 Na1 P1 98.82(9) . 3_646 ?
O5 Na1 P1 21.17(7) 3_646 3_646 ?
O10 Na1 P1 82.58(9) 3_646 3_646 ?
O9 Na1 P1 106.56(11) . 3_646 ?
O9 Na1 P1 76.52(10) 3_646 3_646 ?
O6 Na1 Na1 75.38(10) . 3_656 ?
O10 Na1 Na1 42.99(9) . 3_656 ?
O5 Na1 Na1 103.47(11) 3_646 3_656 ?
O10 Na1 Na1 138.57(12) 3_646 3_656 ?
O9 Na1 Na1 44.75(10) . 3_656 ?
O9 Na1 Na1 132.75(14) 3_646 3_656 ?
P1 Na1 Na1 122.29(8) 3_646 3_656 ?
O6 Na1 Na1 100.94(11) . 3_646 ?
O10 Na1 Na1 136.11(13) . 3_646 ?
O5 Na1 Na1 80.41(9) 3_646 3_646 ?
O10 Na1 Na1 42.00(9) 3_646 3_646 ?
O9 Na1 Na1 138.07(14) . 3_646 ?
O9 Na1 Na1 44.26(10) 3_646 3_646 ?
P1 Na1 Na1 61.24(5) 3_646 3_646 ?
Na1 Na1 Na1 175.77(13) 3_656 3_646 ?
C9 O1 C6 105.0(3) . . ?
C7 O2 H2A 109.5 . . ?
C8 O3 P1 111.9(2) . . ?
C10 O4 P1 121.1(2) . . ?
P1 O5 Na1 123.31(18) . 3_656 ?
P1 O6 Na1 132.93(19) . . ?
H7B O7 H7A 121.9 . . ?
H8B O8 H8A 125.8 . . ?
Na1 O9 Na1 90.98(11) . 3_656 ?
Na1 O9 H9A 109.7 . . ?
Na1 O9 H9A 128.9 3_656 . ?
Na1 O9 H9B 126.6 . . ?
Na1 O9 H9B 115.9 3_656 . ?
H9A O9 H9B 88.9 . . ?
Na1 O10 Na1 95.01(11) . 3_656 ?
Na1 O10 H10C 121.2 . . ?
Na1 O10 H10C 117.5 3_656 . ?
Na1 O10 H10D 117.7 . . ?
Na1 O10 H10D 109.8 3_656 . ?
H10C O10 H10D 96.6 . . ?
H11A O11 H11B 98.4 . . ?
O5 P1 O6 119.43(16) . . ?
O5 P1 O4 110.18(18) . . ?
O6 P1 O4 106.53(17) . . ?
O5 P1 O3 109.66(16) . . ?
O6 P1 O3 106.74(17) . . ?
O4 P1 O3 103.02(13) . . ?
O5 P1 Na1 35.52(13) . 3_656 ?
O6 P1 Na1 89.86(12) . 3_656 ?
O4 P1 Na1 142.80(12) . 3_656 ?
O3 P1 Na1 103.76(10) . 3_656 ?

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
N3 C3 C5 N5 -178.1(3) . . . . ?
N4 C3 C5 N5 0.7(4) . . . . ?
N3 C3 C5 C1 2.7(6) . . . . ?
N4 C3 C5 C1 -178.5(3) . . . . ?
N1 C1 C5 C3 177.1(4) . . . . ?
N2 C1 C5 C3 -3.2(5) . . . . ?
N1 C1 C5 N5 -1.8(6) . . . . ?
N2 C1 C5 N5 177.9(4) . . . . ?
O1 C6 C7 O2 119.2(3) . . . . ?
N4 C6 C7 O2 -118.9(3) . . . . ?
O1 C6 C7 C8 -3.7(3) . . . . ?
N4 C6 C7 C8 118.3(3) . . . . ?
O2 C7 C8 O3 29.4(4) . . . . ?
C6 C7 C8 O3 150.3(3) . . . . ?
O2 C7 C8 C9 -90.9(3) . . . . ?
C6 C7 C8 C9 30.0(3) . . . . ?
O3 C8 C9 O1 -171.4(3) . . . . ?
C7 C8 C9 O1 -47.1(3) . . . . ?
O3 C8 C9 C10 67.1(4) . . . . ?
C7 C8 C9 C10 -168.6(3) . . . . ?
O1 C9 C10 O4 -171.2(3) . . . . ?
C8 C9 C10 O4 -57.4(4) . . . . ?
N3 C2 N2 C1 0.9(7) . . . . ?
N1 C1 N2 C2 -178.6(4) . . . . ?
C5 C1 N2 C2 1.7(5) . . . . ?
C5 C3 N3 C2 -0.4(5) . . . . ?
N4 C3 N3 C2 -178.9(4) . . . . ?
N2 C2 N3 C3 -1.5(6) . . . . ?
N5 C4 N4 C3 0.4(4) . . . . ?
N5 C4 N4 C6 -176.8(4) . . . . ?
N3 C3 N4 C4 178.2(4) . . . . ?
C5 C3 N4 C4 -0.6(4) . . . . ?
N3 C3 N4 C6 -4.5(6) . . . . ?
C5 C3 N4 C6 176.7(3) . . . . ?
O1 C6 N4 C4 63.3(5) . . . . ?
C7 C6 N4 C4 -58.0(5) . . . . ?
O1 C6 N4 C3 -113.5(4) . . . . ?
C7 C6 N4 C3 125.3(4) . . . . ?
N4 C4 N5 C5 0.0(4) . . . . ?
C3 C5 N5 C4 -0.4(4) . . . . ?
C1 C5 N5 C4 178.6(4) . . . . ?
C10 C9 O1 C6 164.9(3) . . . . ?
C8 C9 O1 C6 45.1(3) . . . . ?
N4 C6 O1 C9 -152.2(3) . . . . ?
C7 C6 O1 C9 -26.0(3) . . . . ?
C9 C8 O3 P1 -63.4(3) . . . . ?
C7 C8 O3 P1 -179.3(2) . . . . ?
C9 C10 O4 P1 52.8(4) . . . . ?
O10 Na1 O6 P1 48.6(3) . . . . ?
O5 Na1 O6 P1 -71.1(14) 3_646 . . . ?
O10 Na1 O6 P1 -134.2(3) 3_646 . . . ?
O9 Na1 O6 P1 -34.5(3) . . . . ?
O9 Na1 O6 P1 143.9(3) 3_646 . . . ?
P1 Na1 O6 P1 176.3(2) 3_646 . . . ?
Na1 Na1 O6 P1 8.7(3) 3_656 . . . ?
Na1 Na1 O6 P1 -173.5(2) 3_646 . . . ?
O6 Na1 O9 Na1 70.14(12) . . . 3_656 ?
O10 Na1 O9 Na1 -22.23(10) . . . 3_656 ?
O5 Na1 O9 Na1 -113.46(13) 3_646 . . 3_656 ?
O10 Na1 O9 Na1 155.52(13) 3_646 . . 3_656 ?
O9 Na1 O9 Na1 41(2) 3_646 . . 3_656 ?
P1 Na1 O9 Na1 -119.44(10) 3_646 . . 3_656 ?
Na1 Na1 O9 Na1 175.40(17) 3_646 . . 3_656 ?
O6 Na1 O10 Na1 -65.66(12) . . . 3_656 ?
O5 Na1 O10 Na1 109.11(13) 3_646 . . 3_656 ?
O10 Na1 O10 Na1 -118(2) 3_646 . . 3_656 ?
O9 Na1 O10 Na1 23.00(11) . . . 3_656 ?
O9 Na1 O10 Na1 -154.08(14) 3_646 . . 3_656 ?
P1 Na1 O10 Na1 128.78(11) 3_646 . . 3_656 ?
Na1 Na1 O10 Na1 -173.98(18) 3_646 . . 3_656 ?
Na1 O5 P1 O6 37.3(3) 3_656 . . . ?
Na1 O5 P1 O4 161.05(17) 3_656 . . . ?
Na1 O5 P1 O3 -86.2(2) 3_656 . . . ?
Na1 O6 P1 O5 -29.3(3) . . . . ?
Na1 O6 P1 O4 -154.8(2) . . . . ?
Na1 O6 P1 O3 95.7(3) . . . . ?
Na1 O6 P1 Na1 -8.7(3) . . . 3_656 ?
C10 O4 P1 O5 68.6(3) . . . . ?
C10 O4 P1 O6 -160.4(3) . . . . ?
C10 O4 P1 O3 -48.3(3) . . . . ?
C10 O4 P1 Na1 86.8(3) . . . 3_656 ?
C8 O3 P1 O5 -67.0(3) . . . . ?
C8 O3 P1 O6 162.3(2) . . . . ?
C8 O3 P1 O4 50.3(3) . . . . ?
C8 O3 P1 Na1 -103.7(2) . . . 3_656 ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.086
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone and water'
_chemical_compound_source        Biotogether
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_mo_20140917campna1_0m
_database_code_depnum_ccdc_archive 'CCDC 1026507'
_audit_update_record             
;
2014-09-29 deposited with the CCDC.
2016-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        "ADENOSINE-3',5'-CYCLIC PHOSPHATE SODIUM "
_chemical_name_common            "ADENOSINE-3',5'-CYCLIC PHOSPHATE SODIUM"
_chemical_melting_point          ?
_chemical_formula_moiety         cAMPNa_CH3OH_3H2O
_chemical_formula_sum            'C11 H21 N5 Na O10 P'
_chemical_formula_weight         437.29
_chemical_absolute_configuration ad

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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '

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

_cell_length_a                   6.5021(10)
_cell_length_b                   7.0943(11)
_cell_length_c                   39.198(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1808.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5360
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      27.66

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9400
_exptl_absorpt_correction_T_max  0.9557
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10127
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3198
_reflns_number_gt                3029
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of 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)+(0.0604P)²+1.9407P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_number_reflns         3198
_refine_ls_number_parameters     256
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1279
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.181
_refine_ls_shift/su_max          0.003
_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
P1 P 0.75496(15) -0.33502(13) 0.81565(2) 0.0267(2) Uani 1 1 d . . .
O6 O 0.6189(4) -0.3113(4) 0.84979(6) 0.0280(6) Uani 1 1 d . . .
O4 O 0.7394(5) -0.1630(4) 0.79436(6) 0.0404(6) Uani 1 1 d . . .
N5 N 0.7289(6) 0.4228(4) 0.94924(7) 0.0290(7) Uani 1 1 d . . .
O5 O 0.9868(4) -0.3542(4) 0.83026(6) 0.0330(6) Uani 1 1 d . . .
O1 O 0.4735(4) -0.2934(4) 0.91752(7) 0.0330(6) Uani 1 1 d . . .
H1 H 0.5554 -0.3745 0.9237 0.049 Uiso 1 1 calc R . .
N4 N 0.7452(6) 0.1087(4) 0.94392(7) 0.0257(6) Uani 1 1 d . . .
N3 N 0.7399(6) 0.0188(4) 1.00371(7) 0.0249(6) Uani 1 1 d . . .
C1 C 0.7312(6) 0.4124(5) 1.01501(8) 0.0247(7) Uani 1 1 d . . .
C2 C 0.7353(7) 0.1049(5) 1.03415(8) 0.0278(8) Uani 1 1 d . . .
H2 H 0.7334 0.0256 1.0530 0.033 Uiso 1 1 calc R . .
N2 N 0.7332(5) 0.2898(4) 1.04104(7) 0.0285(7) Uani 1 1 d . . .
C3 C 0.7406(6) 0.1458(5) 0.97853(8) 0.0239(7) Uani 1 1 d . . .
O2 O 0.9491(4) -0.0850(4) 0.90984(7) 0.0317(6) Uani 1 1 d . . .
N1 N 0.7290(6) 0.5966(4) 1.02279(8) 0.0322(7) Uani 1 1 d . . .
H1A H 0.5992 0.6357 1.0242 0.048 Uiso 1 1 d R . .
H1B H 0.7938 0.6609 1.0065 0.048 Uiso 1 1 d R . .
C4 C 0.7324(5) 0.3396(5) 0.98131(8) 0.0223(6) Uani 1 1 d . . .
C7 C 0.5829(6) -0.1349(5) 0.90495(9) 0.0236(8) Uani 1 1 d . . .
H7 H 0.4884 -0.0285 0.9020 0.028 Uiso 1 1 calc R . .
C6 C 0.7621(7) -0.0769(5) 0.92906(8) 0.0257(7) Uani 1 1 d . . .
H6 H 0.7706 -0.1693 0.9476 0.031 Uiso 1 1 calc R . .
C8 C 0.7000(5) -0.1703(5) 0.87175(8) 0.0216(7) Uani 1 1 d . . .
H8 H 0.7097 -0.0515 0.8591 0.026 Uiso 1 1 calc R . .
C5 C 0.7378(7) 0.2794(5) 0.92806(8) 0.0311(8) Uani 1 1 d . . .
H5 H 0.7389 0.2932 0.9045 0.037 Uiso 1 1 calc R . .
O3 O 0.6986(5) -0.5209(4) 0.80093(7) 0.0370(7) Uani 1 1 d . . .
C9 C 0.9121(6) -0.2239(5) 0.88434(8) 0.0245(8) Uani 1 1 d . . .
H9 H 0.9080 -0.3493 0.8948 0.029 Uiso 1 1 calc R . .
O7 O 0.9498(5) 0.1637(6) 0.79441(12) 0.0710(12) Uani 1 1 d . . .
H7A H 0.8809 0.0534 0.7986 0.085 Uiso 1 1 d R . .
H7B H 0.8827 0.2575 0.8035 0.085 Uiso 1 1 d R . .
C10 C 1.0639(6) -0.2225(6) 0.85525(9) 0.0337(9) Uani 1 1 d . . .
H10A H 1.0742 -0.0972 0.8455 0.040 Uiso 1 1 calc R . .
H10B H 1.1990 -0.2608 0.8631 0.040 Uiso 1 1 calc R . .
Na1 Na 0.5045(3) -0.0975(2) 0.74924(4) 0.0347(4) Uani 1 1 d . . .
O11 O 0.2625(5) -0.3447(5) 0.76919(7) 0.0497(8) Uani 1 1 d . . .
H11D H 0.2128 -0.3543 0.7900 0.060 Uiso 1 1 d R . .
H11E H 0.1600 -0.3362 0.7567 0.060 Uiso 1 1 d R . .
O8 O 0.3644(4) 0.1437(4) 0.78404(7) 0.0393(7) Uani 1 1 d . . .
H8A H 0.2433 0.1262 0.7868 0.047 Uiso 1 1 d R . .
H8B H 0.4057 0.1460 0.8053 0.047 Uiso 1 1 d R . .
O9 O 0.4947(6) 0.2445(5) 0.85197(9) 0.0584(9) Uani 1 1 d D . .
H9A H 0.5461 0.3377 0.8430 0.088 Uiso 1 1 calc R . .
C11 C 0.2882(13) 0.3019(11) 0.87013(19) 0.121(3) Uani 1 1 d DU . .
H11A H 0.2464 0.2030 0.8853 0.181 Uiso 1 1 calc R . .
H11B H 0.1833 0.3219 0.8533 0.181 Uiso 1 1 calc R . .
H11C H 0.3090 0.4159 0.8829 0.181 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O4 1.482(3) . ?
P1 O3 1.486(3) . ?
P1 O6 1.613(3) . ?
P1 O5 1.618(3) . ?
O6 C8 1.421(4) . ?
O4 Na1 2.382(3) . ?
N5 C5 1.314(4) . ?
N5 C4 1.389(4) . ?
O5 C10 1.444(5) . ?
O1 C7 1.419(5) . ?
O1 H1 0.8200 . ?
N4 C5 1.362(4) . ?
N4 C3 1.382(4) . ?
N4 C6 1.444(4) . ?
N3 C3 1.336(4) . ?
N3 C2 1.341(4) . ?
C1 N1 1.342(5) . ?
C1 N2 1.341(5) . ?
C1 C4 1.419(5) . ?
C2 N2 1.339(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(5) . ?
O2 C9 1.424(4) . ?
O2 C6 1.431(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C7 C8 1.528(5) . ?
C7 C6 1.556(5) . ?
C7 H7 0.9800 . ?
C6 H6 0.9800 . ?
C8 C9 1.513(5) . ?
C8 H8 0.9800 . ?
C5 H5 0.9300 . ?
O3 Na1 2.430(3) 3_646 ?
C9 C10 1.508(5) . ?
C9 H9 0.9800 . ?
O7 H7A 0.9162 . ?
O7 H7B 0.8718 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
Na1 O8 2.370(3) . ?
Na1 O8 2.409(3) 3_646 ?
Na1 O3 2.430(3) 3_656 ?
Na1 O11 2.457(4) 3_656 ?
Na1 O11 2.482(4) . ?
Na1 Na1 3.5481(6) 3_656 ?
Na1 Na1 3.5481(6) 3_646 ?
O11 Na1 2.457(4) 3_646 ?
O11 H11D 0.8792 . ?
O11 H11E 0.8296 . ?
O8 Na1 2.409(3) 3_656 ?
O8 H8A 0.8046 . ?
O8 H8B 0.8749 . ?
O9 C11 1.573(8) . ?
O9 H9A 0.8200 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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 P1 O3 119.71(15) . . ?
O4 P1 O6 110.11(16) . . ?
O3 P1 O6 106.23(16) . . ?
O4 P1 O5 109.40(18) . . ?
O3 P1 O5 107.01(16) . . ?
O6 P1 O5 103.07(13) . . ?
C8 O6 P1 111.9(2) . . ?
P1 O4 Na1 128.49(18) . . ?
C5 N5 C4 104.0(3) . . ?
C10 O5 P1 120.6(2) . . ?
C7 O1 H1 109.5 . . ?
C5 N4 C3 106.2(3) . . ?
C5 N4 C6 129.0(3) . . ?
C3 N4 C6 124.8(3) . . ?
C3 N3 C2 110.5(3) . . ?
N1 C1 N2 117.3(3) . . ?
N1 C1 C4 124.5(3) . . ?
N2 C1 C4 118.2(3) . . ?
N2 C2 N3 128.8(3) . . ?
N2 C2 H2 115.6 . . ?
N3 C2 H2 115.6 . . ?
C2 N2 C1 118.8(3) . . ?
N3 C3 C4 127.8(3) . . ?
N3 C3 N4 126.6(3) . . ?
C4 C3 N4 105.5(3) . . ?
C9 O2 C6 104.7(3) . . ?
C1 N1 H1A 109.2 . . ?
C1 N1 H1B 109.4 . . ?
H1A N1 H1B 109.5 . . ?
C3 C4 N5 110.7(3) . . ?
C3 C4 C1 115.9(3) . . ?
N5 C4 C1 133.5(3) . . ?
O1 C7 C8 114.5(3) . . ?
O1 C7 C6 112.0(3) . . ?
C8 C7 C6 100.8(3) . . ?
O1 C7 H7 109.7 . . ?
C8 C7 H7 109.7 . . ?
C6 C7 H7 109.7 . . ?
O2 C6 N4 108.3(3) . . ?
O2 C6 C7 107.8(3) . . ?
N4 C6 C7 115.4(3) . . ?
O2 C6 H6 108.4 . . ?
N4 C6 H6 108.4 . . ?
C7 C6 H6 108.4 . . ?
O6 C8 C9 111.0(3) . . ?
O6 C8 C7 116.5(3) . . ?
C9 C8 C7 102.6(3) . . ?
O6 C8 H8 108.8 . . ?
C9 C8 H8 108.8 . . ?
C7 C8 H8 108.8 . . ?
N5 C5 N4 113.6(3) . . ?
N5 C5 H5 123.2 . . ?
N4 C5 H5 123.2 . . ?
P1 O3 Na1 130.30(18) . 3_646 ?
O2 C9 C10 114.6(3) . . ?
O2 C9 C8 102.1(3) . . ?
C10 C9 C8 110.4(3) . . ?
O2 C9 H9 109.8 . . ?
C10 C9 H9 109.9 . . ?
C8 C9 H9 109.9 . . ?
H7A O7 H7B 109.5 . . ?
O5 C10 C9 106.4(3) . . ?
O5 C10 H10A 110.5 . . ?
C9 C10 H10A 110.5 . . ?
O5 C10 H10B 110.5 . . ?
C9 C10 H10B 110.5 . . ?
H10A C10 H10B 108.6 . . ?
O8 Na1 O4 87.70(12) . . ?
O8 Na1 O8 176.51(13) . 3_646 ?
O4 Na1 O8 91.52(11) . 3_646 ?
O8 Na1 O3 95.49(12) . 3_656 ?
O4 Na1 O3 173.01(14) . 3_656 ?
O8 Na1 O3 85.66(11) 3_646 3_656 ?
O8 Na1 O11 83.07(12) . 3_656 ?
O4 Na1 O11 88.00(12) . 3_656 ?
O8 Na1 O11 100.31(12) 3_646 3_656 ?
O3 Na1 O11 86.21(12) 3_656 3_656 ?
O8 Na1 O11 94.88(12) . . ?
O4 Na1 O11 92.00(12) . . ?
O8 Na1 O11 81.74(11) 3_646 . ?
O3 Na1 O11 93.92(12) 3_656 . ?
O11 Na1 O11 177.95(13) 3_656 . ?
O8 Na1 Na1 42.47(8) . 3_656 ?
O4 Na1 Na1 101.13(10) . 3_656 ?
O8 Na1 Na1 140.99(11) 3_646 3_656 ?
O3 Na1 Na1 77.36(9) 3_656 3_656 ?
O11 Na1 Na1 44.37(9) 3_656 3_656 ?
O11 Na1 Na1 133.68(12) . 3_656 ?
O8 Na1 Na1 134.89(12) . 3_646 ?
O4 Na1 Na1 78.65(9) . 3_646 ?
O8 Na1 Na1 41.63(8) 3_646 3_646 ?
O3 Na1 Na1 103.18(10) 3_656 3_646 ?
O11 Na1 Na1 138.15(12) 3_656 3_646 ?
O11 Na1 Na1 43.79(9) . 3_646 ?
Na1 Na1 Na1 177.32(11) 3_656 3_646 ?
Na1 O11 Na1 91.84(11) 3_646 . ?
Na1 O11 H11D 116.3 3_646 . ?
Na1 O11 H11D 125.4 . . ?
Na1 O11 H11E 112.0 3_646 . ?
Na1 O11 H11E 105.8 . . ?
H11D O11 H11E 105.0 . . ?
Na1 O8 Na1 95.89(10) . 3_656 ?
Na1 O8 H8A 110.0 . . ?
Na1 O8 H8A 122.4 3_656 . ?
Na1 O8 H8B 116.3 . . ?
Na1 O8 H8B 113.1 3_656 . ?
H8A O8 H8B 100.1 . . ?
C11 O9 H9A 109.5 . . ?
O9 C11 H11A 109.5 . . ?
O9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_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 P1 O6 C8 -66.9(3) . . . . ?
O3 P1 O6 C8 162.1(2) . . . . ?
O5 P1 O6 C8 49.7(3) . . . . ?
O3 P1 O4 Na1 31.1(3) . . . . ?
O6 P1 O4 Na1 -92.3(2) . . . . ?
O5 P1 O4 Na1 155.06(19) . . . . ?
O4 P1 O5 C10 68.6(3) . . . . ?
O3 P1 O5 C10 -160.3(3) . . . . ?
O6 P1 O5 C10 -48.5(3) . . . . ?
C3 N3 C2 N2 -0.5(7) . . . . ?
N3 C2 N2 C1 1.4(7) . . . . ?
N1 C1 N2 C2 180.0(4) . . . . ?
C4 C1 N2 C2 -0.3(6) . . . . ?
C2 N3 C3 C4 -1.7(6) . . . . ?
C2 N3 C3 N4 179.9(4) . . . . ?
C5 N4 C3 N3 178.2(4) . . . . ?
C6 N4 C3 N3 -3.8(6) . . . . ?
C5 N4 C3 C4 -0.5(4) . . . . ?
C6 N4 C3 C4 177.5(4) . . . . ?
N3 C3 C4 N5 -177.9(4) . . . . ?
N4 C3 C4 N5 0.8(5) . . . . ?
N3 C3 C4 C1 2.7(6) . . . . ?
N4 C3 C4 C1 -178.6(3) . . . . ?
C5 N5 C4 C3 -0.8(5) . . . . ?
C5 N5 C4 C1 178.5(4) . . . . ?
N1 C1 C4 C3 178.2(4) . . . . ?
N2 C1 C4 C3 -1.5(5) . . . . ?
N1 C1 C4 N5 -1.0(7) . . . . ?
N2 C1 C4 N5 179.2(4) . . . . ?
C9 O2 C6 N4 -153.5(3) . . . . ?
C9 O2 C6 C7 -27.9(3) . . . . ?
C5 N4 C6 O2 59.8(5) . . . . ?
C3 N4 C6 O2 -117.8(4) . . . . ?
C5 N4 C6 C7 -61.1(5) . . . . ?
C3 N4 C6 C7 121.3(4) . . . . ?
O1 C7 C6 O2 121.6(3) . . . . ?
C8 C7 C6 O2 -0.6(4) . . . . ?
O1 C7 C6 N4 -117.3(3) . . . . ?
C8 C7 C6 N4 120.5(3) . . . . ?
P1 O6 C8 C9 -63.3(3) . . . . ?
P1 O6 C8 C7 179.8(2) . . . . ?
O1 C7 C8 O6 28.0(4) . . . . ?
C6 C7 C8 O6 148.4(3) . . . . ?
O1 C7 C8 C9 -93.5(3) . . . . ?
C6 C7 C8 C9 26.9(3) . . . . ?
C4 N5 C5 N4 0.5(5) . . . . ?
C3 N4 C5 N5 0.0(5) . . . . ?
C6 N4 C5 N5 -177.9(4) . . . . ?
O4 P1 O3 Na1 -18.2(3) . . . 3_646 ?
O6 P1 O3 Na1 107.2(2) . . . 3_646 ?
O5 P1 O3 Na1 -143.2(2) . . . 3_646 ?
C6 O2 C9 C10 164.6(3) . . . . ?
C6 O2 C9 C8 45.3(3) . . . . ?
O6 C8 C9 O2 -170.4(3) . . . . ?
C7 C8 C9 O2 -45.2(3) . . . . ?
O6 C8 C9 C10 67.4(4) . . . . ?
C7 C8 C9 C10 -167.4(3) . . . . ?
P1 O5 C10 C9 54.0(4) . . . . ?
O2 C9 C10 O5 -172.8(3) . . . . ?
C8 C9 C10 O5 -58.3(4) . . . . ?
P1 O4 Na1 O8 114.3(2) . . . . ?
P1 O4 Na1 O8 -62.3(2) . . . 3_646 ?
P1 O4 Na1 O3 -128.4(10) . . . 3_656 ?
P1 O4 Na1 O11 -162.6(2) . . . 3_656 ?
P1 O4 Na1 O11 19.5(2) . . . . ?
P1 O4 Na1 Na1 154.8(2) . . . 3_656 ?
P1 O4 Na1 Na1 -22.5(2) . . . 3_646 ?
O8 Na1 O11 Na1 -159.14(12) . . . 3_646 ?
O4 Na1 O11 Na1 -71.28(12) . . . 3_646 ?
O8 Na1 O11 Na1 19.97(9) 3_646 . . 3_646 ?
O3 Na1 O11 Na1 105.00(12) 3_656 . . 3_646 ?
O11 Na1 O11 Na1 -161(3) 3_656 . . 3_646 ?
Na1 Na1 O11 Na1 -178.76(15) 3_656 . . 3_646 ?
O4 Na1 O8 Na1 109.27(12) . . . 3_656 ?
O8 Na1 O8 Na1 -173.6(14) 3_646 . . 3_656 ?
O3 Na1 O8 Na1 -64.50(11) 3_656 . . 3_656 ?
O11 Na1 O8 Na1 21.00(10) 3_656 . . 3_656 ?
O11 Na1 O8 Na1 -158.92(13) . . . 3_656 ?
Na1 Na1 O8 Na1 -179.28(16) 3_646 . . 3_656 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.017
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.069
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol and water'
_chemical_compound_source        ' nucleic acid degradation product'
_chemical_properties_physical    Heat-sensitive
