##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Sodium (S)-(+)-6-methoxy-α-methyl-2-naphthaleneacetate
;
_chemical_name_common     'anhydrous sodium naproxen'
_chemical_formula_moiety     'Na 1+, C14 H13 O3'
_chemical_formula_sum     'C14 H13 Na1 O3'
_chemical_formula_iupac     'Na 1+, C14 H13 O3'
_chemical_formula_weight     252.23
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     9.969(3)
_cell_length_b     5.9346(16)
_cell_length_c     20.823(6)
_cell_angle_alpha     90.00
_cell_angle_beta     102.025(5)
_cell_angle_gamma     90.00
_cell_volume     1204.9(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     881
_cell_measurement_theta_min     2.49
_cell_measurement_theta_max     27.4
_cell_measurement_temperature     298(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.71
_exptl_crystal_size_mid     0.61
_exptl_crystal_size_min     0.34
_exptl_crystal_density_diffrn     1.390
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     528
_exptl_absorpt_coefficient_mu     0.127
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(Blessing, 1995)'
_exptl_absorpt_correction_T_min     0.9148
_exptl_absorpt_correction_T_max     0.9581
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'normal-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1000'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6886
_diffrn_reflns_av_R_equivalents     0.0351
_diffrn_reflns_av_sigmaI/netI     0.0597
_diffrn_reflns_theta_min     2.00
_diffrn_reflns_theta_max     26.84
_diffrn_reflns_theta_full     26.84
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.989
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     24
_diffrn_standards_number     112
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     14:00
_diffrn_standards_decay_%     0.3
_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.
;
_reflns_number_total     4036
_reflns_number_gt     3269
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0613
_refine_ls_R_factor_gt     0.0495
_refine_ls_wR_factor_gt     0.1249
_refine_ls_wR_factor_ref     0.1306
_refine_ls_goodness_of_fit_ref     1.014
_refine_ls_restrained_S_all     1.014
_refine_ls_number_reflns     4036
_refine_ls_number_parameters     329
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0807P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.004
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.324
_refine_diff_density_min     -0.350
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     '(Flack, 1983)'
_refine_ls_abs_structure_Flack     0.1(4)
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'
    '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'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 1998'
_computing_structure_solution     'SHELXTL (Bruker, 1998)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'SHELXTL'
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    Na1 -0.10398(10) 0.48664(18) 0.00061(5) 0.0338(3) Uani d . 1 . . Na
    Na2 -0.40560(10) 0.25104(19) -0.00854(5) 0.0346(3) Uani d . 1 . . Na
    O1a -0.33202(19) 0.5662(3) -0.05815(9) 0.0323(4) Uani d . 1 . . O
    O1b -0.06803(19) -0.1564(3) 0.04241(9) 0.0338(5) Uani d . 1 . . O
    O2a -0.43654(18) 0.8879(4) -0.04611(9) 0.0337(5) Uani d . 1 . . O
    C1a -0.7203(3) 1.1676(5) -0.33536(13) 0.0380(7) Uani d . 1 . . C
    H1 -0.7657 1.3092 -0.3332 0.046 Uiso calc R 1 . . H
    C1b 0.1576(3) 0.1591(6) 0.36098(14) 0.0474(8) Uani d . 1 . . C
    H1' 0.1415 0.2942 0.3836 0.057 Uiso calc R 1 . . H
    C2a -0.6072(3) 1.1051(5) -0.28458(12) 0.0326(6) Uani d . 1 . . C
    C2b 0.0641(3) 0.0937(5) 0.30248(13) 0.0381(7) Uani d . 1 . . C
    C3a -0.5566(3) 1.2458(5) -0.23121(13) 0.0347(6) Uani d . 1 . . C
    H3 -0.5955 1.3931 -0.2296 0.042 Uiso calc R 1 . . H
    C3b -0.0535(3) 0.2190(5) 0.27568(14) 0.0425(7) Uani d . 1 . . C
    H3' -0.0733 0.3544 0.2971 0.051 Uiso calc R 1 . . H
    C4b -0.1408(3) 0.1498(6) 0.21891(13) 0.0383(7) Uani d . 1 . . C
    H4' -0.2216 0.2368 0.2020 0.046 Uiso calc R 1 . . H
    C4a -0.4528(3) 1.1775(5) -0.18137(13) 0.0326(6) Uani d . 1 . . C
    H4 -0.4186 1.2794 -0.1459 0.039 Uiso calc R 1 . . H
    C5a -0.3950(3) 0.9616(5) -0.18078(12) 0.0282(6) Uani d . 1 . . C
    C5b -0.1147(3) -0.0449(5) 0.18498(13) 0.0313(6) Uani d . 1 . . C
    C6b -0.0021(3) -0.1694(5) 0.21093(13) 0.0367(7) Uani d . 1 . . C
    H6' 0.0160 -0.3043 0.1888 0.044 Uiso calc R 1 . . H
    C6a -0.4387(3) 0.8258(5) -0.23407(13) 0.0334(6) Uani d . 1 . . C
    H6 -0.3970 0.6805 -0.2354 0.040 Uiso calc R 1 . . H
    C7a -0.5436(3) 0.8935(5) -0.28734(13) 0.0333(6) Uani d . 1 . . C
    C7b 0.0899(3) -0.1058(5) 0.27003(13) 0.0360(7) Uani d . 1 . . C
    C8b 0.2085(3) -0.2346(7) 0.29674(15) 0.0482(8) Uani d . 1 . . C
    H8' 0.2275 -0.3704 0.2752 0.058 Uiso calc R 1 . . H
    C8a -0.5879(3) 0.7558(6) -0.34292(14) 0.0457(8) Uani d . 1 . . C
    H8 -0.5418 0.6160 -0.3468 0.055 Uiso calc R 1 . . H
    C9a -0.6955(3) 0.8202(7) -0.39107(16) 0.0524(9) Uani d . 1 . . C
    H9 -0.7254 0.7240 -0.4284 0.063 Uiso calc R 1 . . H
    C9b 0.2944(3) -0.1669(7) 0.35220(16) 0.0538(9) Uani d . 1 . . C
    H9' 0.3741 -0.2559 0.3696 0.065 Uiso calc R 1 . . H
    C10b 0.2705(3) 0.0296(7) 0.38501(15) 0.0507(9) Uani d . 1 . . C
    C10a -0.7638(3) 1.0262(6) -0.38696(14) 0.0440(8) Uani d . 1 . . C
    C11b -0.2102(3) -0.1069(5) 0.12103(13) 0.0301(6) Uani d . 1 . . C
    H11' -0.2946 -0.0267 0.1191 0.036 Uiso calc R 1 . . H
    C11a -0.2871(3) 0.8862(5) -0.12182(12) 0.0294(6) Uani d . 1 . . C
    H11 -0.2446 1.0203 -0.1011 0.035 Uiso calc R 1 . . H
    C12a -0.3570(2) 0.7688(5) -0.07157(12) 0.0242(5) Uani d . 1 . . C
    C12b -0.1486(2) -0.0253(5) 0.06357(12) 0.0252(5) Uani d . 1 . . C
    C13b -0.2440(3) -0.3571(5) 0.11613(15) 0.0405(7) Uani d . 1 . . C
    H13D -0.2860 -0.4000 0.1518 0.061 Uiso calc R 1 . . H
    H13E -0.1612 -0.4421 0.1183 0.061 Uiso calc R 1 . . H
    H13F -0.3060 -0.3871 0.0752 0.061 Uiso calc R 1 . . H
    C13a -0.1741(3) 0.7452(6) -0.14027(14) 0.0424(7) Uani d . 1 . . C
    H13A -0.1412 0.8179 -0.1752 0.064 Uiso calc R 1 . . H
    H13B -0.2094 0.5990 -0.1545 0.064 Uiso calc R 1 . . H
    H13C -0.1001 0.7296 -0.1028 0.064 Uiso calc R 1 . . H
    C14a -0.9586(4) 1.2517(8) -0.43119(19) 0.0709(12) Uani d . 1 . . C
    H14A -0.9056 1.3876 -0.4291 0.106 Uiso calc R 1 . . H
    H14B -0.9938 1.2371 -0.3919 0.106 Uiso calc R 1 . . H
    H14C -1.0335 1.2577 -0.4685 0.106 Uiso calc R 1 . . H
    C14b 0.3550(5) 0.2839(9) 0.4724(2) 0.0860(15) Uani d . 1 . . C
    H14D 0.2704 0.2867 0.4876 0.129 Uiso calc R 1 . . H
    H14E 0.3563 0.4062 0.4424 0.129 Uiso calc R 1 . . H
    H14F 0.4305 0.2991 0.5092 0.129 Uiso calc R 1 . . H
    O3a -0.8740(2) 1.0633(5) -0.43720(11) 0.0599(7) Uani d . 1 . . O
    O3b 0.3664(3) 0.0764(6) 0.44008(12) 0.0704(8) Uani d . 1 . . O
    O2b -0.17852(19) 0.1665(3) 0.04152(9) 0.0353(5) Uani d . 1 . . O
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Na1 O1b 2 2.259(2) yes
    Na1 O2b . 2.270(2) yes
    Na1 O1b 1_565 2.290(2) yes
    Na1 O1a . 2.394(2) yes
    Na1 C12b 2 3.087(3) ?
    Na1 Na2 . 3.2853(15) ?
    Na1 Na1 2 3.6229(13) ?
    Na1 Na1 2_545 3.6229(13) ?
    Na2 O2a 2_445 2.276(2) yes
    Na2 O2a 1_545 2.291(2) yes
    Na2 O1a . 2.328(2) yes
    Na2 O2b . 2.341(2) yes
    Na2 Na2 2_445 3.5711(13) ?
    Na2 Na2 2_455 3.5711(13) ?
    O1a C12a . 1.248(4) ?
    O1b C12b . 1.262(3) ?
    O1b Na1 2_545 2.259(2) ?
    O1b Na1 1_545 2.290(2) ?
    O2a C12a . 1.259(3) ?
    O2a Na2 2_455 2.276(2) ?
    O2a Na2 1_565 2.291(2) ?
    C1a C10a . 1.361(4) ?
    C1a C2a . 1.425(4) ?
    C1a H1 . 0.9600 ?
    C1b C10b . 1.368(5) ?
    C1b C2b . 1.425(4) ?
    C1b H1' . 0.9600 ?
    C2a C3a . 1.398(4) ?
    C2a C7a . 1.414(4) ?
    C2b C3b . 1.402(4) ?
    C2b C7b . 1.413(4) ?
    C3a C4a . 1.365(4) ?
    C3a H3 . 0.9600 ?
    C3b C4b . 1.377(4) ?
    C3b H3' . 0.9600 ?
    C4b C5b . 1.406(4) ?
    C4b H4' . 0.9600 ?
    C4a C5a . 1.404(4) ?
    C4a H4 . 0.9600 ?
    C5a C6a . 1.367(4) ?
    C5a C11a . 1.522(3) ?
    C5b C6b . 1.358(4) ?
    C5b C11b . 1.512(4) ?
    C6b C7b . 1.424(4) ?
    C6b H6' . 0.9600 ?
    C6a C7a . 1.415(4) ?
    C6a H6 . 0.9600 ?
    C7a C8a . 1.410(4) ?
    C7b C8b . 1.421(4) ?
    C8b C9b . 1.348(4) ?
    C8b H8' . 0.9600 ?
    C8a C9a . 1.362(4) ?
    C8a H8 . 0.9600 ?
    C9a C10a . 1.410(5) ?
    C9a H9 . 0.9600 ?
    C9b C10b . 1.397(6) ?
    C9b H9' . 0.9600 ?
    C10b O3b . 1.360(4) ?
    C10a O3a . 1.368(3) ?
    C11b C13b . 1.521(4) ?
    C11b C12b . 1.533(4) ?
    C11b H11' . 0.9600 ?
    C11a C13a . 1.515(4) ?
    C11a C12a . 1.539(4) ?
    C11a H11 . 0.9600 ?
    C12b O2b . 1.240(3) ?
    C12b Na1 2_545 3.087(3) ?
    C13b H13D . 0.9599 ?
    C13b H13E . 0.9599 ?
    C13b H13F . 0.9599 ?
    C13a H13A . 0.9599 ?
    C13a H13B . 0.9599 ?
    C13a H13C . 0.9599 ?
    C14a O3a . 1.422(5) ?
    C14a H14A . 0.9599 ?
    C14a H14B . 0.9599 ?
    C14a H14C . 0.9599 ?
    C14b O3b . 1.419(6) ?
    C14b H14D . 0.9599 ?
    C14b H14E . 0.9599 ?
    C14b H14F . 0.9599 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1b Na1 O2b 2 . 99.73(8) ?
    O1b Na1 O1b 2 1_565 115.26(7) ?
    O2b Na1 O1b . 1_565 132.02(8) ?
    O1b Na1 O1a 2 . 126.15(9) ?
    O2b Na1 O1a . . 90.38(8) ?
    O1b Na1 O1a 1_565 . 93.94(8) ?
    O1b Na1 C12b 2 2 20.77(7) ?
    O2b Na1 C12b . 2 120.23(8) ?
    O1b Na1 C12b 1_565 2 96.23(8) ?
    O1a Na1 C12b . 2 123.81(8) ?
    O1b Na1 Na2 2 . 125.32(7) ?
    O2b Na1 Na2 . . 45.44(5) ?
    O1b Na1 Na2 1_565 . 118.99(6) ?
    O1a Na1 Na2 . . 45.08(6) ?
    C12b Na1 Na2 2 . 141.64(6) ?
    O1b Na1 Na1 2 2 79.76(7) ?
    O2b Na1 Na1 . 2 157.05(8) ?
    O1b Na1 Na1 1_565 2 36.92(5) ?
    O1a Na1 Na1 . 2 108.59(6) ?
    C12b Na1 Na1 2 2 59.75(6) ?
    Na2 Na1 Na1 . 2 150.03(4) ?
    O1b Na1 Na1 2 2_545 37.50(6) ?
    O2b Na1 Na1 . 2_545 63.23(6) ?
    O1b Na1 Na1 1_565 2_545 135.72(7) ?
    O1a Na1 Na1 . 2_545 129.93(7) ?
    C12b Na1 Na1 2 2_545 57.23(6) ?
    Na2 Na1 Na1 . 2_545 99.74(4) ?
    Na1 Na1 Na1 2 2_545 109.98(5) ?
    O2a Na2 O2a 2_445 1_545 116.65(8) ?
    O2a Na2 O1a 2_445 . 104.47(8) ?
    O2a Na2 O1a 1_545 . 129.53(8) ?
    O2a Na2 O2b 2_445 . 124.00(9) ?
    O2a Na2 O2b 1_545 . 89.96(8) ?
    O1a Na2 O2b . . 90.29(7) ?
    O2a Na2 Na1 2_445 . 122.61(7) ?
    O2a Na2 Na1 1_545 . 118.46(6) ?
    O1a Na2 Na1 . . 46.73(5) ?
    O2b Na2 Na1 . . 43.69(5) ?
    O2a Na2 Na2 2_445 2_445 79.22(7) ?
    O2a Na2 Na2 1_545 2_445 38.40(5) ?
    O1a Na2 Na2 . 2_445 158.93(8) ?
    O2b Na2 Na2 . 2_445 104.97(6) ?
    Na1 Na2 Na2 . 2_445 147.44(4) ?
    O2a Na2 Na2 2_445 2_455 38.72(6) ?
    O2a Na2 Na2 1_545 2_455 141.19(7) ?
    O1a Na2 Na2 . 2_455 66.30(5) ?
    O2b Na2 Na2 . 2_455 127.93(7) ?
    Na1 Na2 Na2 . 2_455 97.79(4) ?
    Na2 Na2 Na2 2_445 2_455 112.39(6) ?
    C12a O1a Na2 . . 143.82(18) ?
    C12a O1a Na1 . . 115.34(16) ?
    Na2 O1a Na1 . . 88.18(8) ?
    C12b O1b Na1 . 2_545 119.83(18) ?
    C12b O1b Na1 . 1_545 130.01(17) ?
    Na1 O1b Na1 2_545 1_545 105.58(8) ?
    C12a O2a Na2 . 2_455 124.91(19) ?
    C12a O2a Na2 . 1_565 128.30(18) ?
    Na2 O2a Na2 2_455 1_565 102.88(8) ?
    C10a C1a C2a . . 119.9(3) ?
    C10a C1a H1 . . 120.1 ?
    C2a C1a H1 . . 120.1 ?
    C10b C1b C2b . . 120.1(3) ?
    C10b C1b H1' . . 119.9 ?
    C2b C1b H1' . . 119.9 ?
    C3a C2a C7a . . 118.2(2) ?
    C3a C2a C1a . . 122.2(3) ?
    C7a C2a C1a . . 119.6(3) ?
    C3b C2b C7b . . 118.3(3) ?
    C3b C2b C1b . . 122.7(3) ?
    C7b C2b C1b . . 119.0(3) ?
    C4a C3a C2a . . 121.2(3) ?
    C4a C3a H3 . . 119.4 ?
    C2a C3a H3 . . 119.4 ?
    C4b C3b C2b . . 120.7(3) ?
    C4b C3b H3' . . 119.7 ?
    C2b C3b H3' . . 119.7 ?
    C3b C4b C5b . . 121.8(3) ?
    C3b C4b H4' . . 119.1 ?
    C5b C4b H4' . . 119.1 ?
    C3a C4a C5a . . 121.5(3) ?
    C3a C4a H4 . . 119.3 ?
    C5a C4a H4 . . 119.3 ?
    C6a C5a C4a . . 118.0(2) ?
    C6a C5a C11a . . 122.2(3) ?
    C4a C5a C11a . . 119.7(2) ?
    C6b C5b C4b . . 118.1(3) ?
    C6b C5b C11b . . 122.3(3) ?
    C4b C5b C11b . . 119.6(2) ?
    C5b C6b C7b . . 122.0(3) ?
    C5b C6b H6' . . 119.0 ?
    C7b C6b H6' . . 119.0 ?
    C5a C6a C7a . . 121.8(3) ?
    C5a C6a H6 . . 119.1 ?
    C7a C6a H6 . . 119.1 ?
    C8a C7a C2a . . 118.8(3) ?
    C8a C7a C6a . . 122.2(3) ?
    C2a C7a C6a . . 119.0(3) ?
    C2b C7b C8b . . 118.9(3) ?
    C2b C7b C6b . . 119.1(3) ?
    C8b C7b C6b . . 122.0(3) ?
    C9b C8b C7b . . 120.2(3) ?
    C9b C8b H8' . . 119.9 ?
    C7b C8b H8' . . 119.9 ?
    C9a C8a C7a . . 120.4(3) ?
    C9a C8a H8 . . 119.8 ?
    C7a C8a H8 . . 119.8 ?
    C8a C9a C10a . . 121.0(3) ?
    C8a C9a H9 . . 119.5 ?
    C10a C9a H9 . . 119.5 ?
    C8b C9b C10b . . 121.7(3) ?
    C8b C9b H9' . . 119.2 ?
    C10b C9b H9' . . 119.2 ?
    O3b C10b C1b . . 125.0(4) yes
    O3b C10b C9b . . 114.9(3) yes
    C1b C10b C9b . . 120.1(3) ?
    C1a C10a O3a . . 125.3(3) yes
    C1a C10a C9a . . 120.3(3) ?
    O3a C10a C9a . . 114.4(3) yes
    C5b C11b C13b . . 112.7(2) ?
    C5b C11b C12b . . 109.2(2) ?
    C13b C11b C12b . . 112.0(2) ?
    C5b C11b H11' . . 107.5 ?
    C13b C11b H11' . . 107.5 ?
    C12b C11b H11' . . 107.5 ?
    C13a C11a C5a . . 113.3(2) ?
    C13a C11a C12a . . 112.8(2) ?
    C5a C11a C12a . . 109.7(2) ?
    C13a C11a H11 . . 106.8 ?
    C5a C11a H11 . . 106.8 ?
    C12a C11a H11 . . 106.8 ?
    O1a C12a O2a . . 124.1(3) ?
    O1a C12a C11a . . 119.4(2) ?
    O2a C12a C11a . . 116.5(2) ?
    O2b C12b O1b . . 123.9(2) ?
    O2b C12b C11b . . 118.3(2) ?
    O1b C12b C11b . . 117.7(2) ?
    O2b C12b Na1 . 2_545 88.50(16) ?
    O1b C12b Na1 . 2_545 39.41(12) ?
    C11b C12b Na1 . 2_545 147.21(17) ?
    C11b C13b H13D . . 109.5 ?
    C11b C13b H13E . . 109.5 ?
    H13D C13b H13E . . 109.5 ?
    C11b C13b H13F . . 109.5 ?
    H13D C13b H13F . . 109.5 ?
    H13E C13b H13F . . 109.5 ?
    C11a C13a H13A . . 109.5 ?
    C11a C13a H13B . . 109.5 ?
    H13A C13a H13B . . 109.5 ?
    C11a C13a H13C . . 109.5 ?
    H13A C13a H13C . . 109.5 ?
    H13B C13a H13C . . 109.5 ?
    O3a C14a H14A . . 109.5 ?
    O3a C14a H14B . . 109.5 ?
    H14A C14a H14B . . 109.5 ?
    O3a C14a H14C . . 109.5 ?
    H14A C14a H14C . . 109.5 ?
    H14B C14a H14C . . 109.5 ?
    O3b C14b H14D . . 109.5 ?
    O3b C14b H14E . . 109.5 ?
    H14D C14b H14E . . 109.5 ?
    O3b C14b H14F . . 109.5 ?
    H14D C14b H14F . . 109.5 ?
    H14E C14b H14F . . 109.5 ?
    C10a O3a C14a . . 117.1(3) ?
    C10b O3b C14b . . 117.7(3) ?
    C12b O2b Na1 . . 146.59(18) ?
    C12b O2b Na2 . . 119.85(16) ?
    Na1 O2b Na2 . . 90.87(8) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1b Na1 Na2 O2a 2 . . 2_445 172.92(10) ?
    O2b Na1 Na2 O2a . . . 2_445 106.93(11) ?
    O1b Na1 Na2 O2a 1_565 . . 2_445 -14.96(10) ?
    O1a Na1 Na2 O2a . . . 2_445 -78.76(10) ?
    C12b Na1 Na2 O2a 2 . . 2_445 -169.13(11) ?
    Na1 Na1 Na2 O2a 2 . . 2_445 -44.64(14) ?
    Na1 Na1 Na2 O2a 2_545 . . 2_445 142.78(8) ?
    O1b Na1 Na2 O2a 2 . . 1_545 10.63(11) ?
    O2b Na1 Na2 O2a . . . 1_545 -55.35(10) ?
    O1b Na1 Na2 O2a 1_565 . . 1_545 -177.25(9) ?
    O1a Na1 Na2 O2a . . . 1_545 118.96(10) ?
    C12b Na1 Na2 O2a 2 . . 1_545 28.59(12) ?
    Na1 Na1 Na2 O2a 2 . . 1_545 153.08(11) ?
    Na1 Na1 Na2 O2a 2_545 . . 1_545 -19.50(8) ?
    O1b Na1 Na2 O1a 2 . . . -108.32(11) ?
    O2b Na1 Na2 O1a . . . . -174.31(12) ?
    O1b Na1 Na2 O1a 1_565 . . . 63.80(10) ?
    C12b Na1 Na2 O1a 2 . . . -90.37(12) ?
    Na1 Na1 Na2 O1a 2 . . . 34.12(12) ?
    Na1 Na1 Na2 O1a 2_545 . . . -138.46(9) ?
    O1b Na1 Na2 O2b 2 . . . 65.98(11) ?
    O1b Na1 Na2 O2b 1_565 . . . -121.90(10) ?
    O1a Na1 Na2 O2b . . . . 174.31(12) ?
    C12b Na1 Na2 O2b 2 . . . 83.94(12) ?
    Na1 Na1 Na2 O2b 2 . . . -151.57(14) ?
    Na1 Na1 Na2 O2b 2_545 . . . 35.85(8) ?
    O1b Na1 Na2 Na2 2 . . 2_445 46.78(14) ?
    O2b Na1 Na2 Na2 . . . 2_445 -19.20(12) ?
    O1b Na1 Na2 Na2 1_565 . . 2_445 -141.09(11) ?
    O1a Na1 Na2 Na2 . . . 2_445 155.11(13) ?
    C12b Na1 Na2 Na2 2 . . 2_445 64.74(15) ?
    Na1 Na1 Na2 Na2 2 . . 2_445 -170.77(10) ?
    Na1 Na1 Na2 Na2 2_545 . . 2_445 16.65(11) ?
    O1b Na1 Na2 Na2 2 . . 2_455 -155.01(8) ?
    O2b Na1 Na2 Na2 . . . 2_455 139.01(9) ?
    O1b Na1 Na2 Na2 1_565 . . 2_455 17.11(8) ?
    O1a Na1 Na2 Na2 . . . 2_455 -46.69(8) ?
    C12b Na1 Na2 Na2 2 . . 2_455 -137.05(9) ?
    Na1 Na1 Na2 Na2 2 . . 2_455 -12.56(12) ?
    Na1 Na1 Na2 Na2 2_545 . . 2_455 174.86(5) ?
    O2a Na2 O1a C12a 2_445 . . . -11.6(3) ?
    O2a Na2 O1a C12a 1_545 . . . 132.9(3) ?
    O2b Na2 O1a C12a . . . . -136.9(3) ?
    Na1 Na2 O1a C12a . . . . -133.0(3) ?
    Na2 Na2 O1a C12a 2_445 . . . 86.1(4) ?
    Na2 Na2 O1a C12a 2_455 . . . -4.9(3) ?
    O2a Na2 O1a Na1 2_445 . . . 121.44(8) ?
    O2a Na2 O1a Na1 1_545 . . . -94.11(10) ?
    O2b Na2 O1a Na1 . . . . -3.93(8) ?
    Na2 Na2 O1a Na1 2_445 . . . -140.94(16) ?
    Na2 Na2 O1a Na1 2_455 . . . 128.07(7) ?
    O1b Na1 O1a C12a 2 . . . -102.1(2) ?
    O2b Na1 O1a C12a . . . . 155.52(19) ?
    O1b Na1 O1a C12a 1_565 . . . 23.3(2) ?
    C12b Na1 O1a C12a 2 . . . -76.9(2) ?
    Na2 Na1 O1a C12a . . . . 151.5(2) ?
    Na1 Na1 O1a C12a 2 . . . -11.3(2) ?
    Na1 Na1 O1a C12a 2_545 . . . -150.06(17) ?
    O1b Na1 O1a Na2 2 . . . 106.42(10) ?
    O2b Na1 O1a Na2 . . . . 4.05(8) ?
    O1b Na1 O1a Na2 1_565 . . . -128.12(8) ?
    C12b Na1 O1a Na2 2 . . . 131.68(9) ?
    Na1 Na1 O1a Na2 2 . . . -162.80(6) ?
    Na1 Na1 O1a Na2 2_545 . . . 58.47(10) ?
    C10a C1a C2a C3a . . . . 178.7(3) ?
    C10a C1a C2a C7a . . . . -1.8(4) ?
    C10b C1b C2b C3b . . . . 179.7(3) ?
    C10b C1b C2b C7b . . . . 0.0(4) ?
    C7a C2a C3a C4a . . . . -3.0(4) ?
    C1a C2a C3a C4a . . . . 176.5(3) ?
    C7b C2b C3b C4b . . . . -0.5(5) ?
    C1b C2b C3b C4b . . . . 179.8(3) ?
    C2b C3b C4b C5b . . . . -1.3(5) ?
    C2a C3a C4a C5a . . . . -1.6(4) ?
    C3a C4a C5a C6a . . . . 4.6(4) ?
    C3a C4a C5a C11a . . . . -175.4(3) ?
    C3b C4b C5b C6b . . . . 2.1(4) ?
    C3b C4b C5b C11b . . . . -176.9(3) ?
    C4b C5b C6b C7b . . . . -1.2(4) ?
    C11b C5b C6b C7b . . . . 177.8(3) ?
    C4a C5a C6a C7a . . . . -3.0(4) ?
    C11a C5a C6a C7a . . . . 177.1(3) ?
    C3a C2a C7a C8a . . . . -176.0(3) ?
    C1a C2a C7a C8a . . . . 4.4(4) ?
    C3a C2a C7a C6a . . . . 4.5(4) ?
    C1a C2a C7a C6a . . . . -175.0(3) ?
    C5a C6a C7a C8a . . . . 179.0(3) ?
    C5a C6a C7a C2a . . . . -1.6(4) ?
    C3b C2b C7b C8b . . . . -179.9(3) ?
    C1b C2b C7b C8b . . . . -0.1(4) ?
    C3b C2b C7b C6b . . . . 1.4(4) ?
    C1b C2b C7b C6b . . . . -178.9(3) ?
    C5b C6b C7b C2b . . . . -0.5(4) ?
    C5b C6b C7b C8b . . . . -179.3(3) ?
    C2b C7b C8b C9b . . . . 0.1(5) ?
    C6b C7b C8b C9b . . . . 178.9(3) ?
    C2a C7a C8a C9a . . . . -4.0(5) ?
    C6a C7a C8a C9a . . . . 175.4(3) ?
    C7a C8a C9a C10a . . . . 0.8(6) ?
    C7b C8b C9b C10b . . . . 0.0(5) ?
    C2b C1b C10b O3b . . . . 179.7(3) ?
    C2b C1b C10b C9b . . . . 0.1(5) ?
    C8b C9b C10b O3b . . . . -179.8(3) ?
    C8b C9b C10b C1b . . . . -0.1(5) ?
    C2a C1a C10a O3a . . . . 177.3(3) ?
    C2a C1a C10a C9a . . . . -1.4(5) ?
    C8a C9a C10a C1a . . . . 1.9(5) ?
    C8a C9a C10a O3a . . . . -177.0(3) ?
    C6b C5b C11b C13b . . . . 44.3(4) ?
    C4b C5b C11b C13b . . . . -136.7(3) ?
    C6b C5b C11b C12b . . . . -80.9(3) ?
    C4b C5b C11b C12b . . . . 98.1(3) ?
    C6a C5a C11a C13a . . . . 37.7(4) ?
    C4a C5a C11a C13a . . . . -142.3(3) ?
    C6a C5a C11a C12a . . . . -89.4(3) ?
    C4a C5a C11a C12a . . . . 90.6(3) ?
    Na2 O1a C12a O2a . . . . 14.9(4) ?
    Na1 O1a C12a O2a . . . . -111.2(2) ?
    Na2 O1a C12a C11a . . . . -165.6(2) ?
    Na1 O1a C12a C11a . . . . 68.4(3) ?
    Na2 O2a C12a O1a 2_455 . . . -16.7(3) ?
    Na2 O2a C12a O1a 1_565 . . . 137.1(2) ?
    Na2 O2a C12a C11a 2_455 . . . 163.68(16) ?
    Na2 O2a C12a C11a 1_565 . . . -42.5(3) ?
    C13a C11a C12a O1a . . . . -10.4(3) ?
    C5a C11a C12a O1a . . . . 117.0(3) ?
    C13a C11a C12a O2a . . . . 169.3(2) ?
    C5a C11a C12a O2a . . . . -63.3(3) ?
    Na1 O1b C12b O2b 2_545 . . . 29.7(3) ?
    Na1 O1b C12b O2b 1_545 . . . -122.6(2) ?
    Na1 O1b C12b C11b 2_545 . . . -148.91(18) ?
    Na1 O1b C12b C11b 1_545 . . . 58.8(3) ?
    Na1 O1b C12b Na1 1_545 . . 2_545 -152.3(3) ?
    C5b C11b C12b O2b . . . . -90.4(3) ?
    C13b C11b C12b O2b . . . . 144.0(2) ?
    C5b C11b C12b O1b . . . . 88.3(3) ?
    C13b C11b C12b O1b . . . . -37.4(3) ?
    C5b C11b C12b Na1 . . . 2_545 51.0(4) ?
    C13b C11b C12b Na1 . . . 2_545 -74.6(4) ?
    C1a C10a O3a C14a . . . . -7.4(5) ?
    C9a C10a O3a C14a . . . . 171.3(4) ?
    C1b C10b O3b C14b . . . . -5.2(5) ?
    C9b C10b O3b C14b . . . . 174.4(4) ?
    O1b C12b O2b Na1 . . . . -37.5(5) ?
    C11b C12b O2b Na1 . . . . 141.1(3) ?
    Na1 C12b O2b Na1 2_545 . . . -19.1(3) ?
    O1b C12b O2b Na2 . . . . 116.9(2) ?
    C11b C12b O2b Na2 . . . . -64.5(3) ?
    Na1 C12b O2b Na2 2_545 . . . 135.22(13) ?
    O1b Na1 O2b C12b 2 . . . 27.1(3) ?
    O1b Na1 O2b C12b 1_565 . . . -110.4(3) ?
    O1a Na1 O2b C12b . . . . 153.9(3) ?
    C12b Na1 O2b C12b 2 . . . 23.5(4) ?
    Na2 Na1 O2b C12b . . . . 158.0(4) ?
    Na1 Na1 O2b C12b 2 . . . -59.6(4) ?
    Na1 Na1 O2b C12b 2_545 . . . 18.2(3) ?
    O1b Na1 O2b Na2 2 . . . -130.87(8) ?
    O1b Na1 O2b Na2 1_565 . . . 91.62(11) ?
    O1a Na1 O2b Na2 . . . . -4.03(8) ?
    C12b Na1 O2b Na2 2 . . . -134.42(8) ?
    Na1 Na1 O2b Na2 2 . . . 142.41(15) ?
    Na1 Na1 O2b Na2 2_545 . . . -139.72(8) ?
    O2a Na2 O2b C12b 2_445 . . . 90.2(2) ?
    O2a Na2 O2b C12b 1_545 . . . -32.5(2) ?
    O1a Na2 O2b C12b . . . . -162.1(2) ?
    Na1 Na2 O2b C12b . . . . -166.2(2) ?
    Na2 Na2 O2b C12b 2_445 . . . 3.2(2) ?
    Na2 Na2 O2b C12b 2_455 . . . 138.31(19) ?
    O2a Na2 O2b Na1 2_445 . . . -103.60(10) ?
    O2a Na2 O2b Na1 1_545 . . . 133.68(8) ?
    O1a Na2 O2b Na1 . . . . 4.14(8) ?
    Na2 Na2 O2b Na1 2_445 . . . 169.44(6) ?
    Na2 Na2 O2b Na1 2_455 . . . -55.47(10) ?
data_global
_journal_data_validation_number     ?
_journal_date_recd_electronic     2004-02-26
_journal_date_accepted     2004-03-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue      4
_journal_page_first     m419
_journal_page_last     m420
_journal_paper_category     EM
_publ_contact_author_name     'Professor Ronald W. Rousseau'
_publ_contact_author_address
;
School of Chemical & Biomolecular Engineering
Georgia Institute of Technology
311 Ferst Drive, NW
Atlanta, GA30332-0100
USA
;
_publ_contact_author_email     ronald.rousseau@chbe.gatech.edu
_publ_contact_author_fax     +1-404-385-0185
_publ_contact_author_phone     +1-404-894-2867
_publ_section_title
;
Anhydrous sodium naproxen, C₁₄H₁₃O₃Na
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Kim, Young-soo' .
;
School of Chemical & Biomolecular Engineering
Georgia Institute of Technology
311 Ferst Drive, NW
Atlanta, GA 30332-0100
USA
;
    'VanDerveer, Don' .
;
School of Chemistry and Biochemistry
Georgia Institute of Technology
Atlanta, GA 30332-0400
USA
;
    'Rousseau, Ronald W.' .
;
School of Chemical & Biomolecular Engineering
Georgia Institute of Technology
311 Ferst Drive, NW
Atlanta, GA 30332-0100
USA
;
    'Wilkinson, Angus P.' .
;
School of Chemistry and Biochemistry
Georgia Institute of Technology
Atlanta, GA 30332-0400
USA
;
