# Supplementary Material (ESI) for PCCP
# This journal is (c) the Owner Societies 2011


data_S_naproxen
_database_code_depnum_ccdc_archive 'CCDC 790000'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Naproxen
;
_chemical_name_common            Naproxen
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 O3'
_chemical_formula_sum            'C14 H14 O3'
_chemical_formula_weight         230.25
_chemical_absolute_configuration .

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1) '

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

_cell_length_a                   7.7354(11)
_cell_length_b                   5.7181(8)
_cell_length_c                   13.3641(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.737(2)
_cell_angle_gamma                90.00
_cell_volume                     589.86(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    102(2)
_cell_measurement_reflns_used    2824
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      28.31

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9690
_exptl_absorpt_correction_T_max  0.9812
_exptl_absorpt_process_details   'R. Blessing, Acta Cryst. (1995) A51 33-38.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      102(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        NO
_diffrn_reflns_number            6007
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         28.32
_reflns_number_total             1611
_reflns_number_gt                1519
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0648P)^2^+0.0465P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1611
_refine_ls_number_parameters     160
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3736(2) 0.3214(3) 0.47711(11) 0.0382(4) Uani 1 1 d . . .
O2 O 0.32803(18) -0.0492(3) 0.42697(10) 0.0287(3) Uani 1 1 d . . .
C1 C 0.2895(2) 0.1762(3) 0.42915(12) 0.0234(4) Uani 1 1 d . . .
C2 C 0.1299(2) 0.2353(3) 0.36204(12) 0.0215(3) Uani 1 1 d . . .
H2 H 0.0512 0.0963 0.3590 0.026 Uiso 1 1 calc R . .
C3 C 0.1892(2) 0.2807(3) 0.25689(12) 0.0199(3) Uani 1 1 d . . .
C4 C 0.1493(2) 0.1239(3) 0.18080(12) 0.0199(3) Uani 1 1 d . . .
H4 H 0.0901 -0.0166 0.1949 0.024 Uiso 1 1 calc R . .
C6 C 0.1955(2) 0.1692(3) 0.08149(11) 0.0187(3) Uani 1 1 d . . .
C7 C 0.14585(19) 0.0155(3) 0.00134(12) 0.0213(3) Uani 1 1 d . . .
H7 H 0.0920 -0.1294 0.0150 0.026 Uiso 1 1 calc R . .
C8 C 0.1749(2) 0.0741(3) -0.09522(12) 0.0235(3) Uani 1 1 d . . .
H8 H 0.1380 -0.0282 -0.1484 0.028 Uiso 1 1 calc R . .
C9 C 0.2597(2) 0.2865(3) -0.11676(12) 0.0215(3) Uani 1 1 d . . .
C10 C 0.3173(2) 0.4351(3) -0.04091(12) 0.0211(3) Uani 1 1 d . . .
H10 H 0.3787 0.5735 -0.0555 0.025 Uiso 1 1 calc R . .
C11 C 0.28364(19) 0.3792(3) 0.06019(12) 0.0184(3) Uani 1 1 d . . .
C12 C 0.3298(2) 0.5334(3) 0.14081(12) 0.0219(3) Uani 1 1 d . . .
H12 H 0.3935 0.6714 0.1286 0.026 Uiso 1 1 calc R . .
C13 C 0.2838(2) 0.4860(3) 0.23619(12) 0.0215(3) Uani 1 1 d . . .
H13 H 0.3156 0.5919 0.2890 0.026 Uiso 1 1 calc R . .
C14 C 0.0317(3) 0.4429(4) 0.40302(14) 0.0298(4) Uani 1 1 d . . .
H14A H -0.0079 0.4030 0.4691 0.045 Uiso 1 1 calc R . .
H14B H -0.0686 0.4796 0.3571 0.045 Uiso 1 1 calc R . .
H14C H 0.1086 0.5791 0.4091 0.045 Uiso 1 1 calc R . .
O3 O 0.27608(17) 0.3227(3) -0.21708(9) 0.0279(3) Uani 1 1 d . . .
C15 C 0.3576(2) 0.5343(4) -0.24564(14) 0.0311(4) Uani 1 1 d . . .
H15A H 0.2935 0.6685 -0.2213 0.047 Uiso 1 1 calc R . .
H15B H 0.3581 0.5415 -0.3189 0.047 Uiso 1 1 calc R . .
H15C H 0.4770 0.5382 -0.2163 0.047 Uiso 1 1 calc R . .
H1 H 0.428(3) -0.082(5) 0.4596(18) 0.041(7) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0397(7) 0.0326(8) 0.0403(8) -0.0051(7) -0.0127(6) -0.0053(7)
O2 0.0296(6) 0.0255(7) 0.0301(7) 0.0012(5) -0.0052(5) 0.0032(5)
C1 0.0259(8) 0.0250(9) 0.0196(7) 0.0008(7) 0.0025(6) -0.0021(7)
C2 0.0230(7) 0.0207(8) 0.0208(7) -0.0002(6) 0.0017(6) -0.0010(6)
C3 0.0187(7) 0.0189(8) 0.0218(7) 0.0006(6) -0.0008(5) 0.0017(6)
C4 0.0192(7) 0.0154(8) 0.0247(8) 0.0015(6) -0.0008(6) 0.0006(6)
C6 0.0175(7) 0.0158(7) 0.0224(8) -0.0001(6) -0.0014(6) 0.0024(6)
C7 0.0205(7) 0.0162(8) 0.0271(8) -0.0013(6) 0.0008(6) 0.0003(6)
C8 0.0241(7) 0.0215(8) 0.0246(8) -0.0053(7) 0.0001(6) 0.0016(7)
C9 0.0205(7) 0.0233(9) 0.0209(8) -0.0010(6) 0.0026(5) 0.0033(6)
C10 0.0203(7) 0.0188(8) 0.0243(8) -0.0014(6) 0.0029(6) 0.0002(6)
C11 0.0162(7) 0.0158(8) 0.0232(7) -0.0012(6) 0.0011(5) 0.0013(5)
C12 0.0226(7) 0.0165(8) 0.0264(8) -0.0019(6) 0.0010(6) -0.0030(6)
C13 0.0231(7) 0.0189(8) 0.0224(7) -0.0040(6) -0.0006(6) -0.0017(6)
C14 0.0323(9) 0.0300(9) 0.0279(8) -0.0011(8) 0.0079(7) 0.0052(8)
O3 0.0321(6) 0.0302(7) 0.0217(6) -0.0019(6) 0.0045(5) -0.0018(6)
C15 0.0363(10) 0.0322(10) 0.0259(8) 0.0039(8) 0.0089(7) 0.0016(8)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.212(2) . ?
O2 C1 1.324(2) . ?
O2 H1 0.88(3) . ?
C1 C2 1.516(2) . ?
C2 C3 1.529(2) . ?
C2 C14 1.530(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.375(2) . ?
C3 C13 1.420(2) . ?
C4 C6 1.420(2) . ?
C4 H4 0.9500 . ?
C6 C11 1.419(2) . ?
C6 C7 1.419(2) . ?
C7 C8 1.366(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.419(3) . ?
C8 H8 0.9500 . ?
C9 O3 1.371(2) . ?
C9 C10 1.375(2) . ?
C10 C11 1.429(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.420(2) . ?
C12 C13 1.373(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O3 C15 1.428(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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 H1 113(2) . . ?
O1 C1 O2 124.38(18) . . ?
O1 C1 C2 123.26(18) . . ?
O2 C1 C2 112.33(15) . . ?
C1 C2 C3 107.45(13) . . ?
C1 C2 C14 111.44(15) . . ?
C3 C2 C14 112.53(14) . . ?
C1 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
C14 C2 H2 108.4 . . ?
C4 C3 C13 119.23(15) . . ?
C4 C3 C2 120.19(15) . . ?
C13 C3 C2 120.58(14) . . ?
C3 C4 C6 120.94(15) . . ?
C3 C4 H4 119.5 . . ?
C6 C4 H4 119.5 . . ?
C11 C6 C7 118.87(14) . . ?
C11 C6 C4 119.68(14) . . ?
C7 C6 C4 121.34(15) . . ?
C8 C7 C6 120.52(15) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.56(15) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
O3 C9 C10 125.58(16) . . ?
O3 C9 C8 113.66(15) . . ?
C10 C9 C8 120.77(15) . . ?
C9 C10 C11 119.25(15) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C6 C11 C12 118.29(14) . . ?
C6 C11 C10 119.92(14) . . ?
C12 C11 C10 121.74(15) . . ?
C13 C12 C11 120.94(15) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C3 120.82(15) . . ?
C12 C13 H13 119.6 . . ?
C3 C13 H13 119.6 . . ?
C2 C14 H14A 109.5 . . ?
C2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 O3 C15 117.39(14) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H1 O1 0.88(3) 1.79(3) 2.6703(19) 174(3) 2_646

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.043