# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_NaMOF-LT
#============================================================================== 

_audit_creation_date             2013-06-12T15:13:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C14 H8 Na2 O5'
_chemical_formula_weight         302.18

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   27.720(6)
_cell_length_b                   5.8060(12)
_cell_length_c                   7.5530(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.70(3)
_cell_angle_gamma                90
_cell_volume                     1214.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    95(2)

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      95(2)
_diffrn_radiation_wavelength     0.64999
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_number            16907
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         33.36
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.849
_reflns_number_total             5223
_reflns_number_gt                4824
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0504P)²+0.7811P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5223
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.035
_refine_ls_wR_factor_ref         0.0997
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.869
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.078

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O2 O 0.30981(2) 0.19507(10) 0.75495(8) 0.00645(10) Uani 1 1 d . . .
OW1 O 0.25016(2) -0.03371(10) 0.51187(7) 0.00619(10) Uani 1 1 d . . .
Na1 Na 0.283726(12) -0.13589(6) 0.88579(4) 0.00506(7) Uani 1 1 d . . .
Na2 Na 0.223402(12) 0.40623(6) 0.72914(4) 0.00521(7) Uani 1 1 d . . .
O4 O 0.18667(2) -0.22998(10) 0.73717(8) 0.00670(10) Uani 1 1 d . . .
O1 O 0.30637(2) -0.43384(10) 0.67982(7) 0.00502(10) Uani 1 1 d . . .
O3 O 0.20585(2) 0.07292(10) 0.90797(8) 0.00538(10) Uani 1 1 d . . .
C1 C 0.32814(2) 0.39322(12) 0.74728(9) 0.00294(11) Uani 1 1 d . . .
C5 C 0.47477(2) 0.48536(12) 0.96330(9) 0.00305(11) Uani 1 1 d . . .
C3 C 0.40206(3) 0.25237(13) 0.92100(10) 0.00491(11) Uani 1 1 d . . .
H3 H 0.3857 0.1113 0.9394 0.006 Uiso 1 1 calc R . .
C6 C 0.45103(3) 0.65996(13) 0.86395(10) 0.00561(12) Uani 1 1 d . . .
H6 H 0.4676 0.7996 0.8422 0.007 Uiso 1 1 calc R . .
C2 C 0.37873(2) 0.42770(12) 0.82446(9) 0.00279(11) Uani 1 1 d . . .
C10 C 0.10733(3) 0.14760(13) 0.97549(10) 0.00594(12) Uani 1 1 d . . .
H10 H 0.1294 0.2675 1.0072 0.007 Uiso 1 1 calc R . .
C9 C 0.12349(2) -0.04582(12) 0.88604(9) 0.00329(11) Uani 1 1 d . . .
C4 C 0.44905(3) 0.28123(13) 0.99092(10) 0.00553(12) Uani 1 1 d . . .
H4 H 0.464 0.1606 1.0585 0.007 Uiso 1 1 calc R . .
C12 C 0.02564(2) -0.00824(12) 0.97524(9) 0.00339(11) Uani 1 1 d . . .
C14 C 0.09035(3) -0.21822(14) 0.83861(11) 0.00740(13) Uani 1 1 d . . .
H14 H 0.1006 -0.3492 0.7751 0.009 Uiso 1 1 calc R . .
C11 C 0.05918(3) 0.16682(13) 1.01884(11) 0.00641(12) Uani 1 1 d . . .
H11 H 0.0488 0.3005 1.0789 0.008 Uiso 1 1 calc R . .
C13 C 0.04236(3) -0.20012(14) 0.88355(11) 0.00783(13) Uani 1 1 d . . .
H13 H 0.0205 -0.3205 0.8514 0.009 Uiso 1 1 calc R . .
C8 C 0.17553(2) -0.07043(12) 0.84115(9) 0.00317(11) Uani 1 1 d . . .
C7 C 0.40367(3) 0.63262(13) 0.79664(10) 0.00516(12) Uani 1 1 d . . .
H7 H 0.3883 0.7541 0.7315 0.006 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O2 C1 1.2602(9) . ?
O2 Na1 2.2933(8) . ?
O2 Na2 2.6896(8) . ?
OW1 Na2 2.3470(8) 4_565 ?
OW1 Na1 2.3529(8) 4 ?
OW1 Na1 2.9910(10) . ?
Na1 O1 2.3148(8) 4_556 ?
Na1 OW1 2.3529(8) 4_556 ?
Na1 O1 2.4288(8) . ?
Na1 O3 2.4884(8) . ?
Na1 O4 2.9174(10) . ?
Na1 C8 3.0263(10) . ?
Na1 Na2 3.3282(7) 1_545 ?
Na1 Na2 3.4218(9) 4_566 ?
Na1 Na2 3.7304(8) . ?
Na1 Na1 4.0022(7) 4 ?
Na2 O4 2.3467(8) 1_565 ?
Na2 OW1 2.3470(8) 4_566 ?
Na2 O3 2.4225(8) . ?
Na2 O3 2.4545(8) 4_565 ?
Na2 O1 2.5241(8) 1_565 ?
Na2 C1 2.9012(10) . ?
Na2 Na1 3.3282(7) 1_565 ?
Na2 Na1 3.4218(9) 4_565 ?
Na2 Na2 4.1896(8) 4_565 ?
Na2 Na2 4.1896(8) 4_566 ?
O4 C8 1.2622(9) . ?
O4 Na2 2.3467(8) 1_545 ?
O1 C1 1.2662(9) 1_545 ?
O1 Na1 2.3148(8) 4 ?
O1 Na2 2.5241(8) 1_545 ?
O3 C8 1.2703(9) . ?
O3 Na2 2.4545(9) 4_566 ?
C1 O1 1.2662(9) 1_565 ?
C1 C2 1.5064(10) . ?
C5 C4 1.4037(10) . ?
C5 C6 1.4060(11) . ?
C5 C5 1.4901(14) 3_667 ?
C3 C4 1.3923(10) . ?
C3 C2 1.3935(10) . ?
C6 C7 1.3942(11) . ?
C2 C7 1.3969(10) . ?
C10 C11 1.3937(11) . ?
C10 C9 1.3952(10) . ?
C9 C14 1.3939(11) . ?
C9 C8 1.5042(10) . ?
C12 C13 1.4021(11) . ?
C12 C11 1.4061(11) . ?
C12 C12 1.4900(14) 3_557 ?
C14 C13 1.3923(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
C1 O2 Na1 157.04(5) . . ?
C1 O2 Na2 86.58(5) . . ?
Na1 O2 Na2 96.63(3) . . ?
Na2 OW1 Na1 90.17(3) 4_565 4 ?
Na2 OW1 Na1 173.00(3) 4_565 . ?
Na1 OW1 Na1 96.26(2) 4 . ?
O2 Na1 O1 100.96(3) . 4_556 ?
O2 Na1 OW1 175.06(3) . 4_556 ?
O1 Na1 OW1 81.30(3) 4_556 4_556 ?
O2 Na1 O1 102.98(3) . . ?
O1 Na1 O1 132.26(3) 4_556 . ?
OW1 Na1 O1 78.32(3) 4_556 . ?
O2 Na1 O3 85.01(3) . . ?
O1 Na1 O3 92.69(3) 4_556 . ?
OW1 Na1 O3 90.52(3) 4_556 . ?
O1 Na1 O3 129.89(3) . . ?
O2 Na1 O4 107.15(3) . . ?
O1 Na1 O4 127.25(3) 4_556 . ?
OW1 Na1 O4 68.16(2) 4_556 . ?
O1 Na1 O4 83.20(3) . . ?
O3 Na1 O4 47.93(2) . . ?
O2 Na1 OW1 61.13(2) . . ?
O1 Na1 OW1 158.34(2) 4_556 . ?
OW1 Na1 OW1 115.63(3) 4_556 . ?
O1 Na1 OW1 67.34(2) . . ?
O3 Na1 OW1 74.62(3) . . ?
O4 Na1 OW1 55.51(3) . . ?
O2 Na1 C8 100.24(3) . . ?
O1 Na1 C8 107.90(4) 4_556 . ?
OW1 Na1 C8 74.85(2) 4_556 . ?
O1 Na1 C8 107.62(3) . . ?
O3 Na1 C8 24.209(19) . . ?
O4 Na1 C8 24.434(19) . . ?
OW1 Na1 C8 66.88(3) . . ?
O2 Na1 Na2 132.80(2) . 1_545 ?
O1 Na1 Na2 126.14(2) 4_556 1_545 ?
OW1 Na1 Na2 44.845(19) 4_556 1_545 ?
O1 Na1 Na2 49.01(2) . 1_545 ?
O3 Na1 Na2 89.44(2) . 1_545 ?
O4 Na1 Na2 43.523(16) . 1_545 ?
OW1 Na1 Na2 72.19(2) . 1_545 ?
C8 Na1 Na2 65.29(2) . 1_545 ?
O2 Na1 Na2 100.10(3) . 4_566 ?
O1 Na1 Na2 47.53(2) 4_556 4_566 ?
OW1 Na1 Na2 78.13(2) 4_556 4_566 ?
O1 Na1 Na2 155.96(2) . 4_566 ?
O3 Na1 Na2 45.78(2) . 4_566 ?
O4 Na1 Na2 83.68(2) . 4_566 ?
OW1 Na1 Na2 119.80(2) . 4_566 ?
C8 Na1 Na2 61.20(3) . 4_566 ?
Na2 Na1 Na2 108.989(19) 1_545 4_566 ?
O2 Na1 Na2 45.74(2) . . ?
O1 Na1 Na2 104.71(2) 4_556 . ?
OW1 Na1 Na2 129.52(2) 4_556 . ?
O1 Na1 Na2 121.56(2) . . ?
O3 Na1 Na2 39.914(18) . . ?
O4 Na1 Na2 69.18(2) . . ?
OW1 Na1 Na2 54.434(17) . . ?
C8 Na1 Na2 55.365(18) . . ?
Na2 Na1 Na2 110.55(2) 1_545 . ?
Na2 Na1 Na2 71.568(14) 4_566 . ?
O2 Na1 Na1 81.76(2) . 4 ?
O1 Na1 Na1 162.012(19) 4_556 4 ?
OW1 Na1 Na1 97.44(2) 4_556 4 ?
O1 Na1 Na1 31.599(16) . 4 ?
O3 Na1 Na1 105.28(3) . 4 ?
O4 Na1 Na1 67.42(3) . 4 ?
OW1 Na1 Na1 35.760(15) . 4 ?
C8 Na1 Na1 88.89(3) . 4 ?
Na2 Na1 Na1 54.722(17) 1_545 4 ?
Na2 Na1 Na1 149.987(13) 4_566 4 ?
Na2 Na1 Na1 90.002(18) . 4 ?
O4 Na2 OW1 79.14(3) 1_565 4_566 ?
O4 Na2 O3 127.29(3) 1_565 . ?
OW1 Na2 O3 78.92(3) 4_566 . ?
O4 Na2 O3 85.13(3) 1_565 4_565 ?
OW1 Na2 O3 157.38(3) 4_566 4_565 ?
O3 Na2 O3 123.70(2) . 4_565 ?
O4 Na2 O1 94.14(3) 1_565 1_565 ?
OW1 Na2 O1 76.54(3) 4_566 1_565 ?
O3 Na2 O1 125.77(3) . 1_565 ?
O3 Na2 O1 88.60(3) 4_565 1_565 ?
O4 Na2 O2 142.59(2) 1_565 . ?
OW1 Na2 O2 80.54(3) 4_566 . ?
O3 Na2 O2 78.29(3) . . ?
O3 Na2 O2 103.21(3) 4_565 . ?
O1 Na2 O2 50.50(2) 1_565 . ?
O4 Na2 C1 117.17(2) 1_565 . ?
OW1 Na2 C1 72.10(3) 4_566 . ?
O3 Na2 C1 100.36(3) . . ?
O3 Na2 C1 101.49(4) 4_565 . ?
O1 Na2 C1 25.81(2) 1_565 . ?
O2 Na2 C1 25.695(19) . . ?
O4 Na2 Na1 58.88(2) 1_565 1_565 ?
OW1 Na2 Na1 44.988(19) 4_566 1_565 ?
O3 Na2 Na1 123.41(2) . 1_565 ?
O3 Na2 Na1 112.63(2) 4_565 1_565 ?
O1 Na2 Na1 46.577(18) 1_565 1_565 ?
O2 Na2 Na1 84.70(2) . 1_565 ?
C1 Na2 Na1 61.26(2) . 1_565 ?
O4 Na2 Na1 84.09(2) 1_565 4_565 ?
OW1 Na2 Na1 114.96(2) 4_566 4_565 ?
O3 Na2 Na1 148.44(2) . 4_565 ?
O3 Na2 Na1 46.60(2) 4_565 4_565 ?
O1 Na2 Na1 42.57(2) 1_565 4_565 ?
O2 Na2 Na1 76.54(3) . 4_565 ?
C1 Na2 Na1 61.46(3) . 4_565 ?
Na1 Na2 Na1 72.714(15) 1_565 4_565 ?
O4 Na2 Na1 160.00(2) 1_565 . ?
OW1 Na2 Na1 81.94(2) 4_566 . ?
O3 Na2 Na1 41.232(19) . . ?
O3 Na2 Na1 114.84(2) 4_565 . ?
O1 Na2 Na1 87.67(2) 1_565 . ?
O2 Na2 Na1 37.636(16) . . ?
C1 Na2 Na1 61.994(19) . . ?
Na1 Na2 Na1 110.55(2) 1_565 . ?
Na1 Na2 Na1 109.961(18) 4_565 . ?
O4 Na2 Na2 115.56(2) 1_565 4_565 ?
OW1 Na2 Na2 160.602(18) 4_566 4_565 ?
O3 Na2 Na2 99.51(2) . 4_565 ?
O3 Na2 Na2 30.565(15) 4_565 4_565 ?
O1 Na2 Na2 89.28(3) 1_565 4_565 ?
O2 Na2 Na2 80.22(3) . 4_565 ?
C1 Na2 Na2 89.35(3) . 4_565 ?
Na1 Na2 Na2 130.162(17) 1_565 4_565 ?
Na1 Na2 Na2 57.642(16) 4_565 4_565 ?
Na1 Na2 Na2 84.35(2) . 4_565 ?
O4 Na2 Na2 110.36(2) 1_565 4_566 ?
OW1 Na2 Na2 47.923(19) 4_566 4_566 ?
O3 Na2 Na2 31.013(16) . 4_566 ?
O3 Na2 Na2 154.66(2) 4_565 4_566 ?
O1 Na2 Na2 109.34(3) 1_565 4_566 ?
O2 Na2 Na2 77.01(3) . 4_566 ?
C1 Na2 Na2 89.35(3) . 4_566 ?
Na1 Na2 Na2 92.68(2) 1_565 4_566 ?
Na1 Na2 Na2 150.770(12) 4_565 4_566 ?
Na1 Na2 Na2 50.790(16) . 4_566 ?
Na2 Na2 Na2 128.68(2) 4_565 4_566 ?
C8 O4 Na2 142.74(5) . 1_545 ?
C8 O4 Na1 82.62(5) . . ?
Na2 O4 Na1 77.60(2) 1_545 . ?
C1 O1 Na1 128.85(5) 1_545 4 ?
C1 O1 Na1 116.09(5) 1_545 . ?
Na1 O1 Na1 115.05(3) 4 . ?
C1 O1 Na2 93.97(5) 1_545 1_545 ?
Na1 O1 Na2 89.90(3) 4 1_545 ?
Na1 O1 Na2 84.42(3) . 1_545 ?
C8 O3 Na2 116.64(5) . . ?
C8 O3 Na2 121.44(5) . 4_566 ?
Na2 O3 Na2 118.42(3) . 4_566 ?
C8 O3 Na1 102.35(5) . . ?
Na2 O3 Na1 98.85(3) . . ?
Na2 O3 Na1 87.62(3) 4_566 . ?
O2 C1 O1 123.83(7) . 1_565 ?
O2 C1 C2 118.28(6) . . ?
O1 C1 C2 117.89(6) 1_565 . ?
O2 C1 Na2 67.73(4) . . ?
O1 C1 Na2 60.22(4) 1_565 . ?
C2 C1 Na2 157.84(5) . . ?
C4 C5 C6 117.39(7) . . ?
C4 C5 C5 121.03(8) . 3_667 ?
C6 C5 C5 121.59(8) . 3_667 ?
C4 C3 C2 120.89(7) . . ?
C7 C6 C5 121.42(7) . . ?
C3 C2 C7 118.69(6) . . ?
C3 C2 C1 120.40(6) . . ?
C7 C2 C1 120.88(6) . . ?
C11 C10 C9 120.73(7) . . ?
C14 C9 C10 118.67(7) . . ?
C14 C9 C8 120.08(6) . . ?
C10 C9 C8 121.25(6) . . ?
C3 C4 C5 121.18(7) . . ?
C13 C12 C11 117.37(7) . . ?
C13 C12 C12 121.10(8) . 3_557 ?
C11 C12 C12 121.53(8) . 3_557 ?
C13 C14 C9 120.58(7) . . ?
C10 C11 C12 121.14(7) . . ?
C14 C13 C12 121.49(7) . . ?
O4 C8 O3 123.45(7) . . ?
O4 C8 C9 118.39(6) . . ?
O3 C8 C9 118.15(6) . . ?
O4 C8 Na1 72.95(4) . . ?
O3 C8 Na1 53.44(4) . . ?
C9 C8 Na1 160.53(5) . . ?
C6 C7 C2 120.42(7) . . ?
#=============================================================================#
#     End of CIF
#=============================================================================# 
_database_code_depnum_ccdc_archive 'CCDC 944127'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_NaMOF-HT
#============================================================================== 

_audit_creation_date             2013-06-12T15:50:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic


#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C14 H9 N0 Na O4'
_chemical_formula_weight         264.2

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.6550(7)
_cell_length_b                   11.214(2)
_cell_length_c                   12.985(3)
_cell_angle_alpha                89.55(3)
_cell_angle_beta                 84.39(3)
_cell_angle_gamma                88.78(3)
_cell_volume                     529.54(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.69999
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_number            5622
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         29.55
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.932
_diffrn_measured_fraction_theta_max 0.912
_reflns_number_total             2827
_reflns_number_gt                2257
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.1537P)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_number_reflns         2827
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1859
_refine_ls_wR_factor_gt          0.172
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.887
_refine_diff_density_rms         0.122

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
H44 H -0.225(7) 0.2484(17) -0.0167(18) 0.067(10) Uiso 1 1 d . . .
Na1 Na 0 0 0 0.0197(2) Uani 1 2 d S . .
Na2 Na 0.5 -0.5 0 0.0360(3) Uani 1 2 d S . .
O3 O -0.4737(3) 0.08330(10) -0.10091(8) 0.0181(3) Uani 1 1 d . . .
O4 O -0.3400(3) 0.27614(10) -0.09216(8) 0.0191(3) Uani 1 1 d . . .
O2 O 0.0859(3) -0.20775(10) -0.06914(8) 0.0189(3) Uani 1 1 d . . .
O1 O 0.0345(3) -0.40457(10) -0.08431(8) 0.0198(3) Uani 1 1 d . . .
C13 C -0.4110(4) -0.33488(13) -0.60368(11) 0.0167(3) Uani 1 1 d . . .
H13 H -0.4441 -0.4109 -0.5717 0.02 Uiso 1 1 calc R . .
C10 C -0.6985(4) 0.11522(13) -0.30035(11) 0.0166(3) Uani 1 1 d . . .
H10 H -0.7414 0.0403 -0.2672 0.02 Uiso 1 1 calc R . .
C12 C -0.5163(4) 0.31964(13) -0.29364(11) 0.0164(3) Uani 1 1 d . . .
H12 H -0.433 0.3846 -0.2563 0.02 Uiso 1 1 calc R . .
C4 C -0.1078(4) -0.36629(13) -0.39827(11) 0.0164(3) Uani 1 1 d . . .
H4 H -0.0771 -0.4329 -0.4433 0.02 Uiso 1 1 calc R . .
C1 C 0.0158(4) -0.30087(13) -0.11970(11) 0.0154(3) Uani 1 1 d . . .
C2 C -0.0817(4) -0.28334(13) -0.22844(11) 0.0156(3) Uani 1 1 d . . .
C8 C -0.2907(4) -0.24083(13) -0.54704(11) 0.0149(3) Uani 1 1 d . . .
C6 C -0.2738(4) -0.16070(13) -0.36766(11) 0.0161(3) Uani 1 1 d . . .
H6 H -0.3591 -0.0858 -0.3916 0.019 Uiso 1 1 calc R . .
C3 C -0.0379(4) -0.37946(13) -0.29534(11) 0.0168(3) Uani 1 1 d . . .
H3 H 0.0405 -0.4549 -0.2707 0.02 Uiso 1 1 calc R . .
C7 C -0.2020(4) -0.17303(13) -0.26450(11) 0.0156(3) Uani 1 1 d . . .
H7 H -0.2348 -0.1068 -0.2191 0.019 Uiso 1 1 calc R . .
C9 C -0.2312(4) -0.13053(13) -0.59700(11) 0.0157(3) Uani 1 1 d . . .
H9 H -0.1424 -0.0659 -0.5604 0.019 Uiso 1 1 calc R . .
C14 C -0.4594(4) 0.18534(13) -0.13883(11) 0.0158(3) Uani 1 1 d . . .
C5 C -0.2231(4) -0.25588(13) -0.43632(11) 0.0153(3) Uani 1 1 d . . .
C11 C -0.5664(4) 0.20844(13) -0.24581(10) 0.0150(3) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Na1 O3 2.4195(14) 1_655 ?
Na1 O3 2.4195(14) 2_455 ?
Na1 O3 2.4378(13) . ?
Na1 O3 2.4378(13) 2 ?
Na1 O2 2.5057(13) 2 ?
Na1 O2 2.5057(13) . ?
Na1 Na1 3.6550(7) 1_455 ?
Na1 Na1 3.6550(7) 1_655 ?
Na2 O1 2.3465(13) 2_645 ?
Na2 O1 2.3465(13) . ?
Na2 O1 2.4111(14) 2_545 ?
Na2 O1 2.4111(14) 1_655 ?
Na2 O4 2.8150(14) 1_645 ?
Na2 O4 2.8150(14) 2 ?
Na2 Na2 3.6550(7) 1_455 ?
Na2 Na2 3.6550(7) 1_655 ?
O3 C14 1.2422(17) . ?
O3 Na1 2.4195(14) 1_455 ?
O4 C14 1.2941(19) . ?
O4 Na2 2.8150(14) 1_465 ?
O2 C1 1.2816(19) . ?
O1 C1 1.2500(17) . ?
O1 Na2 2.4111(14) 1_455 ?
C13 C12 1.3932(18) 2_454 ?
C13 C8 1.393(2) . ?
C10 C11 1.388(2) . ?
C10 C9 1.3905(18) 2_454 ?
C12 C13 1.3932(18) 2_454 ?
C12 C11 1.3963(19) . ?
C4 C3 1.3913(18) . ?
C4 C5 1.4012(19) . ?
C1 C2 1.5002(18) . ?
C2 C3 1.386(2) . ?
C2 C7 1.3967(18) . ?
C8 C9 1.403(2) . ?
C8 C5 1.4902(19) . ?
C6 C5 1.394(2) . ?
C6 C7 1.3952(17) . ?
C9 C10 1.3905(18) 2_454 ?
C14 C11 1.4987(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
O3 Na1 O3 180.00(6) 1_655 2_455 ?
O3 Na1 O3 97.61(4) 1_655 . ?
O3 Na1 O3 82.39(4) 2_455 . ?
O3 Na1 O3 82.39(4) 1_655 2 ?
O3 Na1 O3 97.61(4) 2_455 2 ?
O3 Na1 O3 180.00(6) . 2 ?
O3 Na1 O2 83.60(5) 1_655 2 ?
O3 Na1 O2 96.40(5) 2_455 2 ?
O3 Na1 O2 77.49(4) . 2 ?
O3 Na1 O2 102.51(4) 2 2 ?
O3 Na1 O2 96.40(5) 1_655 . ?
O3 Na1 O2 83.60(5) 2_455 . ?
O3 Na1 O2 102.51(4) . . ?
O3 Na1 O2 77.49(4) 2 . ?
O2 Na1 O2 180.00(5) 2 . ?
O3 Na1 Na1 138.62(3) 1_655 1_455 ?
O3 Na1 Na1 41.38(3) 2_455 1_455 ?
O3 Na1 Na1 41.01(3) . 1_455 ?
O3 Na1 Na1 138.99(3) 2 1_455 ?
O2 Na1 Na1 85.95(4) 2 1_455 ?
O2 Na1 Na1 94.05(4) . 1_455 ?
O3 Na1 Na1 41.38(3) 1_655 1_655 ?
O3 Na1 Na1 138.62(3) 2_455 1_655 ?
O3 Na1 Na1 138.99(3) . 1_655 ?
O3 Na1 Na1 41.01(3) 2 1_655 ?
O2 Na1 Na1 94.05(4) 2 1_655 ?
O2 Na1 Na1 85.95(4) . 1_655 ?
Na1 Na1 Na1 180 1_455 1_655 ?
O1 Na2 O1 180.00(6) 2_645 . ?
O1 Na2 O1 100.38(4) 2_645 2_545 ?
O1 Na2 O1 79.62(4) . 2_545 ?
O1 Na2 O1 79.62(4) 2_645 1_655 ?
O1 Na2 O1 100.38(4) . 1_655 ?
O1 Na2 O1 180 2_545 1_655 ?
O1 Na2 O4 71.28(4) 2_645 1_645 ?
O1 Na2 O4 108.72(4) . 1_645 ?
O1 Na2 O4 84.89(4) 2_545 1_645 ?
O1 Na2 O4 95.11(4) 1_655 1_645 ?
O1 Na2 O4 108.72(4) 2_645 2 ?
O1 Na2 O4 71.28(4) . 2 ?
O1 Na2 O4 95.11(4) 2_545 2 ?
O1 Na2 O4 84.89(4) 1_655 2 ?
O4 Na2 O4 180 1_645 2 ?
O1 Na2 Na2 139.54(3) 2_645 1_455 ?
O1 Na2 Na2 40.46(3) . 1_455 ?
O1 Na2 Na2 39.16(3) 2_545 1_455 ?
O1 Na2 Na2 140.84(3) 1_655 1_455 ?
O4 Na2 Na2 98.47(4) 1_645 1_455 ?
O4 Na2 Na2 81.53(4) 2 1_455 ?
O1 Na2 Na2 40.46(3) 2_645 1_655 ?
O1 Na2 Na2 139.54(3) . 1_655 ?
O1 Na2 Na2 140.84(3) 2_545 1_655 ?
O1 Na2 Na2 39.16(3) 1_655 1_655 ?
O4 Na2 Na2 81.53(4) 1_645 1_655 ?
O4 Na2 Na2 98.47(4) 2 1_655 ?
Na2 Na2 Na2 180 1_455 1_655 ?
C14 O3 Na1 125.56(10) . 1_455 ?
C14 O3 Na1 122.87(10) . . ?
Na1 O3 Na1 97.61(4) 1_455 . ?
C14 O4 Na2 147.56(9) . 1_465 ?
C1 O2 Na1 157.62(9) . . ?
C1 O1 Na2 130.12(10) . . ?
C1 O1 Na2 121.32(10) . 1_455 ?
Na2 O1 Na2 100.38(4) . 1_455 ?
C12 C13 C8 121.28(13) 2_454 . ?
C11 C10 C9 120.61(13) . 2_454 ?
C13 C12 C11 119.73(14) 2_454 . ?
C3 C4 C5 120.74(14) . . ?
O1 C1 O2 123.59(13) . . ?
O1 C1 C2 118.85(14) . . ?
O2 C1 C2 117.53(13) . . ?
C3 C2 C7 119.63(13) . . ?
C3 C2 C1 118.27(12) . . ?
C7 C2 C1 122.07(14) . . ?
C13 C8 C9 118.36(12) . . ?
C13 C8 C5 121.42(14) . . ?
C9 C8 C5 120.21(14) . . ?
C5 C6 C7 121.41(13) . . ?
C2 C3 C4 120.48(13) . . ?
C6 C7 C2 119.56(14) . . ?
C10 C9 C8 120.47(14) 2_454 . ?
O3 C14 O4 123.40(13) . . ?
O3 C14 C11 120.64(14) . . ?
O4 C14 C11 115.90(13) . . ?
C6 C5 C4 118.16(12) . . ?
C6 C5 C8 120.95(13) . . ?
C4 C5 C8 120.89(14) . . ?
C10 C11 C12 119.49(12) . . ?
C10 C11 C14 119.05(13) . . ?
C12 C11 C14 121.36(13) . . ?
#=============================================================================#
#     End of CIF
#=============================================================================# 

_database_code_depnum_ccdc_archive 'CCDC 944128'
