#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:04:12 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179650 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/03/4510385.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4510385
loop_
_publ_author_name
'Rossi, Patrizia'
'Macedi, Eleonora'
'Paoli, Paola'
'Bernazzani, Luca'
'Carignani, Elisa'
'Borsacchi, Silvia'
'Geppi, Marco'
_publ_section_title
;
 Solid--Solid Transition between Hydrated Racemic Compound and Anhydrous
 Conglomerate in Na-Ibuprofen: A Combined X-ray Diffraction, Solid-State
 NMR, Calorimetric, and Computational Study
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2441
_journal_paper_doi               10.1021/cg500161e
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         '(C13 H17 O2)-, Na +, (H2 O) 2'
_chemical_formula_sum            'C13 H21 Na O4'
_chemical_formula_weight         264.29
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                82.940(9)
_cell_angle_beta                 84.447(9)
_cell_angle_gamma                63.140(12)
_cell_formula_units_Z            2
_cell_length_a                   5.7035(7)
_cell_length_b                   5.9553(7)
_cell_length_c                   23.535(2)
_cell_measurement_reflns_used    1612
_cell_measurement_temperature    15
_cell_measurement_theta_max      31.9572
_cell_measurement_theta_min      4.1333
_cell_volume                     706.97(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'ORTEP-3 (Farruggia, 1997)'
_computing_publication_material  'PARST97 (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      15
_diffrn_detector_area_resol_mean 16.4547
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0967
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            8417
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.03
_diffrn_reflns_theta_min         4.14
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.823
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         4437
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.1103
_refine_ls_R_factor_gt           0.0723
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0822P)²+0.2787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1689
_refine_ls_wR_factor_ref         0.1972
_reflns_number_gt                2917
_reflns_number_total             4437
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg500161e_si_001.cif
_cod_data_source_block           RS-H15
_cod_depositor_comments
'Adding full bibliography for 4510385--4510388.cif.'
_cod_original_cell_volume        706.97(13)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4510385
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Na1 Na -0.81817(17) 0.37589(16) 0.05797(4) 0.0117(2) Uani 1 1 d . . .
O1W O -0.7501(3) 0.3167(3) -0.04222(7) 0.0127(3) Uani 1 1 d D . .
H1WA H -0.724(5) 0.178(4) -0.0529(11) 0.015 Uiso 1 1 d D . .
H1WB H -0.608(4) 0.323(5) -0.0474(11) 0.015 Uiso 1 1 d D . .
O2W O -0.7460(3) 0.7339(3) 0.03319(7) 0.0126(3) Uani 1 1 d D . .
H2WA H -0.750(5) 0.787(5) -0.0016(7) 0.015 Uiso 1 1 d D . .
H2WB H -0.833(5) 0.865(4) 0.0515(9) 0.015 Uiso 1 1 d D . .
O1 O 0.0126(3) 0.1090(3) 0.10170(6) 0.0119(3) Uani 1 1 d . . .
O2 O -0.3795(3) 0.1491(3) 0.08160(6) 0.0118(3) Uani 1 1 d . . .
C1 C -0.2281(4) 0.1741(4) 0.11367(9) 0.0101(4) Uani 1 1 d . . .
C2 C -0.3393(4) 0.2836(4) 0.17117(9) 0.0109(4) Uani 1 1 d . . .
H2 H -0.2556 0.3935 0.1776 0.013 Uiso 1 1 calc R . .
C3 C -0.6369(4) 0.4473(4) 0.17343(9) 0.0146(4) Uani 1 1 d . . .
H3A H -0.6943 0.5113 0.2113 0.022 Uiso 1 1 calc R . .
H3B H -0.7252 0.3457 0.1665 0.022 Uiso 1 1 calc R . .
H3C H -0.6822 0.5897 0.1439 0.022 Uiso 1 1 calc R . .
C4 C -0.2550(4) 0.0679(4) 0.21833(9) 0.0112(4) Uani 1 1 d . . .
C5 C -0.3648(4) -0.1010(4) 0.22525(9) 0.0135(4) Uani 1 1 d . . .
H5 H -0.4913 -0.0838 0.1995 0.016 Uiso 1 1 calc R . .
C6 C -0.2918(4) -0.2943(4) 0.26932(9) 0.0138(4) Uani 1 1 d . . .
H6 H -0.3697 -0.4069 0.2732 0.017 Uiso 1 1 calc R . .
C7 C -0.1066(4) -0.3257(4) 0.30781(9) 0.0131(4) Uani 1 1 d . A .
C8 C 0.0069(4) -0.1592(4) 0.30025(9) 0.0140(4) Uani 1 1 d . . .
H8 H 0.1364 -0.1787 0.3255 0.017 Uiso 1 1 calc R . .
C9 C -0.0669(4) 0.0353(4) 0.25621(9) 0.0124(4) Uani 1 1 d . . .
H9 H 0.0122 0.1471 0.2520 0.015 Uiso 1 1 calc R . .
C10 C -0.0275(5) -0.5344(4) 0.35613(9) 0.0150(4) Uani 1 1 d . . .
H10A H 0.0730 -0.5011 0.3832 0.018 Uiso 0.542(5) 1 calc PR A 1
H10B H 0.0914 -0.6962 0.3401 0.018 Uiso 0.542(5) 1 calc PR A 1
H10C H 0.1668 -0.6281 0.3553 0.018 Uiso 0.458(5) 1 d PR A 2
H10D H -0.0966 -0.6541 0.3495 0.018 Uiso 0.458(5) 1 d PR A 2
C12 C -0.4311(6) -0.3116(6) 0.41852(12) 0.0360(7) Uani 1 1 d . . .
H12A H -0.5808 -0.3250 0.4401 0.054 Uiso 0.542(5) 1 calc PR A 1
H12B H -0.4958 -0.1695 0.3889 0.054 Uiso 0.542(5) 1 calc PR A 1
H12C H -0.3251 -0.2836 0.4447 0.054 Uiso 0.542(5) 1 calc PR A 1
H12D H -0.4948 -0.1675 0.3894 0.054 Uiso 0.458(5) 1 d PR A 2
H12E H -0.4968 -0.2524 0.4566 0.054 Uiso 0.458(5) 1 d PR A 2
H12F H -0.4945 -0.4329 0.4112 0.054 Uiso 0.458(5) 1 d PR A 2
C11A C -0.2565(9) -0.5643(9) 0.38933(19) 0.0207(10) Uiso 0.542(5) 1 d P A 1
H11A H -0.3639 -0.5919 0.3623 0.025 Uiso 0.542(5) 1 calc PR A 1
C13A C -0.1549(10) -0.7882(9) 0.4349(2) 0.0244(11) Uiso 0.542(5) 1 d P A 1
H13A H -0.3042 -0.8048 0.4559 0.037 Uiso 0.542(5) 1 calc PR A 1
H13B H -0.0515 -0.7600 0.4617 0.037 Uiso 0.542(5) 1 calc PR A 1
H13C H -0.0437 -0.9433 0.4165 0.037 Uiso 0.542(5) 1 calc PR A 1
C11B C -0.1254(11) -0.4413(11) 0.4159(2) 0.0230(13) Uiso 0.458(5) 1 d P A 2
H11B H -0.0606 -0.3168 0.4227 0.028 Uiso 0.458(5) 1 calc PR A 2
C13B C -0.0268(12) -0.6633(11) 0.4619(2) 0.0260(13) Uiso 0.458(5) 1 d P A 2
H13D H -0.0906 -0.6014 0.4998 0.039 Uiso 0.458(5) 1 calc PR A 2
H13E H 0.1660 -0.7471 0.4599 0.039 Uiso 0.458(5) 1 calc PR A 2
H13F H -0.0925 -0.7840 0.4555 0.039 Uiso 0.458(5) 1 calc PR A 2
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'
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
O1 Na1 O2 100.59(6) 1_455 .
O1 Na1 O1W 88.42(6) 1_455 2_365
O2 Na1 O1W 166.38(7) . 2_365
O1 Na1 O2W 161.84(7) 1_455 .
O2 Na1 O2W 88.86(6) . .
O1W Na1 O2W 79.82(6) 2_365 .
O1 Na1 O1W 107.84(6) 1_455 .
O2 Na1 O1W 97.02(6) . .
O1W Na1 O1W 89.80(6) 2_365 .
O2W Na1 O1W 86.08(6) . .
O1 Na1 Na1 101.50(5) 1_455 2_365
O2 Na1 Na1 139.96(6) . 2_365
O1W Na1 Na1 45.53(4) 2_365 2_365
O2W Na1 Na1 80.09(5) . 2_365
O1W Na1 Na1 44.26(4) . 2_365
Na1 O1W Na1 90.20(6) 2_365 .
C1 O1 Na1 124.57(13) . 1_655
C1 O2 Na1 136.31(14) . .
O1 C1 O2 123.96(19) . .
O1 C1 C2 117.21(18) . .
O2 C1 C2 118.81(18) . .
C4 C2 C3 111.96(17) . .
C4 C2 C1 108.58(17) . .
C3 C2 C1 113.89(17) . .
C9 C4 C5 118.2(2) . .
C9 C4 C2 120.71(18) . .
C5 C4 C2 121.12(18) . .
C6 C5 C4 120.9(2) . .
C5 C6 C7 121.2(2) . .
C6 C7 C8 117.9(2) . .
C6 C7 C10 121.51(19) . .
C8 C7 C10 120.62(19) . .
C9 C8 C7 121.0(2) . .
C4 C9 C8 120.84(19) . .
C7 C10 C11A 114.7(2) . .
C7 C10 C11B 114.1(3) . .
C11A C10 C11B 57.8(3) . .
C11B C12 C11A 56.3(3) . .
C10 C11A C13A 110.5(3) . .
C10 C11A C12 107.6(3) . .
C13A C11A C12 110.1(3) . .
C13B C11B C10 110.3(4) . .
C13B C11B C12 109.3(4) . .
C10 C11B C12 108.4(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Na1 O1 2.3043(17) 1_455
Na1 O2 2.3288(17) .
Na1 O1W 2.3428(18) 2_365
Na1 O2W 2.3445(17) .
Na1 O1W 2.3955(18) .
Na1 Na1 3.3566(17) 2_365
O1W Na1 2.3428(18) 2_365
O1 C1 1.259(2) .
O1 Na1 2.3043(17) 1_655
O2 C1 1.268(2) .
C1 C2 1.528(3) .
C2 C4 1.519(3) .
C2 C3 1.528(3) .
C4 C9 1.392(3) .
C4 C5 1.393(3) .
C5 C6 1.390(3) .
C6 C7 1.391(3) .
C7 C8 1.396(3) .
C7 C10 1.512(3) .
C8 C9 1.393(3) .
C10 C11A 1.525(5) .
C10 C11B 1.535(6) .
C12 C11B 1.554(7) .
C12 C11A 1.580(6) .
C11A C13A 1.528(6) .
C11B C13B 1.527(8) .
