#------------------------------------------------------------------------------
#$Date: 2025-08-21 04:34:05 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301843 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/27/4512747.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_4512747
loop_
_publ_author_name
'Ostrowska, Kinga'
'Kropidłowska, Magdalena'
'Katrusiak, Andrzej'
_publ_section_title
;
 High-Pressure Crystallization and Structural Transformations in
 CompressedR,S-Ibuprofen
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1512
_journal_paper_doi               10.1021/cg5018888
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C13 H18 O2'
_chemical_formula_sum            'C13 H18 O2'
_chemical_formula_weight         206.27
_chemical_melting_point          349
_chemical_name_common
;
(R,S)-2-(4-(2-methylpropyl)phenyl)propanoic acid
;
_chemical_name_systematic
;
 (R,S)-ibuprofen
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.27(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.865(2)
_cell_length_b                   7.4064(15)
_cell_length_c                   9.977(10)
_cell_measurement_pressure       2650000
_cell_measurement_reflns_used    1598
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.47
_cell_measurement_theta_min      3.40
_cell_volume                     1008.1(10)
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_molecular_graphics
;X-Seed (Barbour, 2001) 
and POV-Ray (Persistence of Vision, 2004)

Mercury (2008)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 16.4
_diffrn_measured_fraction_theta_full 0.307
_diffrn_measured_fraction_theta_max 0.307
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method
;HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56085
_diffrn_reflns_av_R_equivalents  0.3115
_diffrn_reflns_av_sigmaI/netI    0.2574
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            10795
_diffrn_reflns_theta_full        28.47
_diffrn_reflns_theta_max         28.47
_diffrn_reflns_theta_min         3.40
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (1990)).
;
_exptl_crystal_colour            colurless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.06(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1598
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.3194
_refine_ls_R_factor_gt           0.1185
_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)+(0.1912P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2768
_refine_ls_wR_factor_ref         0.3898
_reflns_number_gt                496
_reflns_number_total             1598
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5018888_si_002.cif
_cod_data_source_block           ibuprofen_265
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 4512740--4512754.cif.
;
_cod_original_sg_symbol_Hall     '-P 2y bc'
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4512747
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'
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
O2 O 0.5036(3) 0.1874(6) 0.5706(9) 0.045(3) Uani 1 1 d U
O1 O 0.6268(3) -0.0120(6) 0.5977(9) 0.044(3) Uani 1 1 d U
H01 H 0.5841 -0.0755 0.5537 0.053 Uiso 1 1 calc R
C7 C 0.6590(5) 0.2796(9) 0.6867(16) 0.039(3) Uani 1 1 d U
H7A H 0.7123 0.2140 0.7442 0.047 Uiso 1 1 calc R
C1 C 0.7012(4) 0.3854(8) 0.5888(14) 0.036(3) Uani 1 1 d U
C9 C 0.5892(4) 0.1481(8) 0.6200(14) 0.037(3) Uani 1 1 d U
C11 C 0.9089(4) 0.7857(9) 0.3483(15) 0.037(3) Uani 1 1 d U
H11A H 0.9506 0.7159 0.4196 0.045 Uiso 1 1 calc R
C4 C 0.7805(4) 0.5656(9) 0.3862(16) 0.041(3) Uani 1 1 d U
C5 C 0.8300(4) 0.4230(8) 0.4623(16) 0.039(3) Uani 1 1 d U
H5A H 0.8917 0.3899 0.4465 0.046 Uiso 1 1 calc R
C10 C 0.8234(4) 0.6631(9) 0.2785(16) 0.044(3) Uani 1 1 d U
H10A H 0.7734 0.7361 0.2232 0.053 Uiso 1 1 calc R
H10B H 0.8476 0.5764 0.2195 0.053 Uiso 1 1 calc R
C6 C 0.7915(4) 0.3330(9) 0.5565(15) 0.041(3) Uani 1 1 d U
H6A H 0.8249 0.2350 0.6009 0.049 Uiso 1 1 calc R
C3 C 0.6890(5) 0.6093(9) 0.4100(16) 0.043(3) Uani 1 1 d U
H3A H 0.6517 0.6944 0.3550 0.051 Uiso 1 1 calc R
C2 C 0.6494(5) 0.5253(9) 0.5191(15) 0.043(3) Uani 1 1 d U
H2A H 0.5906 0.5646 0.5416 0.051 Uiso 1 1 calc R
C13 C 0.8697(5) 0.9488(9) 0.4132(16) 0.047(4) Uani 1 1 d U
H13A H 0.9232 1.0265 0.4506 0.071 Uiso 1 1 calc R
H13B H 0.8363 0.9098 0.4845 0.071 Uiso 1 1 calc R
H13C H 0.8249 1.0134 0.3455 0.071 Uiso 1 1 calc R
C12 C 0.9691(5) 0.8395(9) 0.2413(15) 0.044(4) Uani 1 1 d U
H12A H 1.0205 0.9203 0.2810 0.066 Uiso 1 1 calc R
H12B H 0.9276 0.8986 0.1669 0.066 Uiso 1 1 calc R
H12C H 0.9973 0.7335 0.2084 0.066 Uiso 1 1 calc R
C8 C 0.6038(6) 0.3979(10) 0.7840(18) 0.057(4) Uani 1 1 d U
H8A H 0.5775 0.3198 0.8453 0.086 Uiso 1 1 calc R
H8B H 0.5515 0.4644 0.7297 0.086 Uiso 1 1 calc R
H8C H 0.6494 0.4806 0.8354 0.086 Uiso 1 1 calc R
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
O2 0.0231(19) 0.057(3) 0.058(9) -0.004(3) 0.014(3) -0.0054(18)
O1 0.036(2) 0.045(3) 0.047(9) 0.006(3) -0.005(3) 0.0050(18)
C7 0.036(3) 0.045(3) 0.040(10) 0.014(4) 0.019(5) -0.005(3)
C1 0.036(3) 0.039(3) 0.030(10) -0.004(4) -0.002(5) 0.002(2)
C9 0.030(3) 0.041(3) 0.042(10) -0.006(4) 0.017(4) 0.001(2)
C11 0.023(2) 0.053(3) 0.038(10) -0.002(4) 0.009(5) 0.001(2)
C4 0.034(3) 0.041(3) 0.053(10) 0.003(4) 0.024(5) 0.003(3)
C5 0.030(3) 0.044(4) 0.043(10) -0.007(4) 0.012(5) 0.004(3)
C10 0.035(3) 0.046(4) 0.054(10) 0.000(4) 0.015(5) -0.003(3)
C6 0.028(3) 0.042(4) 0.053(10) 0.005(4) 0.004(5) -0.002(2)
C3 0.032(3) 0.046(4) 0.052(10) 0.003(4) 0.011(5) 0.004(3)
C2 0.030(3) 0.041(3) 0.054(10) -0.005(4) -0.002(5) 0.002(2)
C13 0.046(3) 0.051(4) 0.043(11) -0.007(4) 0.003(5) -0.001(3)
C12 0.036(3) 0.050(4) 0.047(10) 0.005(4) 0.006(5) -0.005(3)
C8 0.052(4) 0.057(4) 0.062(11) 0.005(5) 0.011(6) 0.012(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0056 0.0036 '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
C9 C7 C8 107.2(7)
C9 C7 C1 111.7(12)
C8 C7 C1 113.9(7)
C2 C1 C6 120.0(11)
C2 C1 C7 120.5(7)
C6 C1 C7 119.2(7)
O2 C9 O1 121.4(7)
O2 C9 C7 122.7(6)
O1 C9 C7 115.2(6)
C13 C11 C12 112.0(7)
C13 C11 C10 110.8(6)
C12 C11 C10 107.9(11)
C5 C4 C3 117.5(10)
C5 C4 C10 122.0(7)
C3 C4 C10 120.5(8)
C4 C5 C6 122.4(7)
C4 C10 C11 109.1(12)
C5 C6 C1 120.5(8)
C2 C3 C4 121.1(9)
C1 C2 C3 118.1(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C9 1.236(8)
O1 C9 1.330(8)
C7 C9 1.448(12)
C7 C8 1.600(19)
C7 C1 1.455(17)
C1 C2 1.376(12)
C1 C6 1.402(11)
C11 C13 1.516(13)
C11 C12 1.522(17)
C11 C10 1.556(11)
C4 C5 1.406(13)
C4 C3 1.370(11)
C4 C10 1.503(18)
C5 C6 1.338(17)
C3 C2 1.444(19)
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
C9 C7 C1 C2 78.5(11)
C8 C7 C1 C2 -43.1(14)
C9 C7 C1 C6 -95.5(10)
C8 C7 C1 C6 142.9(9)
C8 C7 C9 O2 44.3(17)
C1 C7 C9 O2 -81.1(14)
C8 C7 C9 O1 -145.0(10)
C1 C7 C9 O1 89.5(10)
C3 C4 C5 C6 -1.1(17)
C10 C4 C5 C6 -178.6(11)
C5 C4 C10 C11 -72.9(12)
C3 C4 C10 C11 109.6(10)
C13 C11 C10 C4 -73.2(10)
C12 C11 C10 C4 163.9(6)
C4 C5 C6 C1 -3.7(17)
C2 C1 C6 C5 2.9(16)
C7 C1 C6 C5 176.9(11)
C5 C4 C3 C2 6.6(17)
C10 C4 C3 C2 -175.9(11)
C6 C1 C2 C3 2.4(15)
C7 C1 C2 C3 -171.6(11)
C4 C3 C2 C1 -7.3(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 114864
