#------------------------------------------------------------------------------
#$Date: 2023-11-06 09:25:17 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287339 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/74/7247476.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_7247476
loop_
_publ_author_name
'Poręba, Tomasz'
'Świątkowski, Marcin'
'Confalonieri, Giorgia'
_publ_section_title
;
 Melting pseudosymmetry and thermal expansion in 3-benzoylpropionic acid
;
_journal_issue                   42
_journal_name_full               CrystEngComm
_journal_page_first              5932
_journal_page_last               5941
_journal_paper_doi               10.1039/D3CE00940H
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C10 H10 O3'
_chemical_formula_sum            'C10 H10 O3'
_chemical_formula_weight         178.18
_chemical_name_common            '3-benzoylpropionic acid'
_chemical_name_systematic        '3-benzoylpropionic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2023-06-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-07-20 deposited with the CCDC.	2023-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.423(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7932(5)
_cell_length_b                   5.23468(18)
_cell_length_c                   14.4811(6)
_cell_measurement_reflns_used    4573
_cell_measurement_temperature    269.99(10)
_cell_measurement_theta_max      75.5300
_cell_measurement_theta_min      3.9300
_cell_volume                     902.77(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      269.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     42.00  83.00   0.50    1.50    --  110.00 -68.00 138.00   82
  2  ω     45.00 105.00   0.50    1.50    --  110.00 -77.00  60.00  120
  3  ω     38.00  66.00   0.50    1.50    --  110.00 -57.00 -30.00   56
  4  ω     38.00  66.00   0.50    1.50    --  110.00 -57.00 -60.00   56
  5  ω     38.00  66.00   0.50    1.50    --  110.00 -57.00 -90.00   56
  6  ω     38.00  66.00   0.50    1.50    --  110.00 -57.00-180.00   56
  7  ω     38.00  66.00   0.50    1.50    --  110.00 -57.00 120.00   56
  8  ω     26.00 114.00   0.50    0.30    --   49.12  77.00  90.00  176
  9  ω     26.00 114.00   0.50    0.30    --   49.12  77.00 -30.00  176
 10  ω     62.00 120.00   0.50    0.30    --   49.12 178.00-120.00  116
 11  ω     26.00 114.00   0.50    0.30    --   49.12  77.00-150.00  176
 12  ω    -26.00  27.00   0.50    0.30    --  -49.12  19.00 -60.00  106
 13  ω     60.00 122.00   0.50    0.30    --   49.12-178.00   0.00  124
 14  ω    -26.00  27.00   0.50    0.30    --  -49.12  19.00   0.00  106
 15  ω    -26.00  27.00   0.50    0.30    --  -49.12  19.00  30.00  106
 16  ω    -26.00  27.00   0.50    0.30    --  -49.12  19.00 150.00  106
 17  ω    -66.00 -17.00   0.50    1.50    --  -88.50  57.00  60.00   98
 18  ω    -43.00 -13.00   0.50    1.50    --  -88.50  38.00  90.00   60
 19  ω    -43.00 -13.00   0.50    1.50    --  -88.50  38.00  30.00   60
 20  ω    -43.00 -13.00   0.50    1.50    --  -88.50  38.00 150.00   60
 21  ω    -43.00 -13.00   0.50    1.50    --  -88.50  38.00   0.00   60
 22  ω    -43.00 -13.00   0.50    1.50    --  -88.50  38.00-120.00   60
 23  ω    -43.00 -13.00   0.50    1.50    --  -88.50  38.00-180.00   60
 24  ω    -43.00 -13.00   0.50    1.50    --  -88.50  38.00-150.00   60
 25  ω    -43.00 -13.00   0.50    1.50    --  -88.50  38.00 -90.00   60
 26  ω   -164.00 -75.00   0.50    1.50    --  -88.50 -19.00   0.00  178
 27  ω   -160.00-127.00   0.50    1.50    --  -88.50 -57.00 120.00   66
 28  ω   -120.00 -41.00   0.50    0.30    --  -49.12-178.00 -60.00  158
 29  ω   -157.00 -85.00   0.50    1.50    --  -88.50 -99.00 -30.00  144
 30  ω   -154.00 -65.00   0.50    1.50    --  -88.50 -77.00 -60.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0104505000
_diffrn_orient_matrix_UB_12      -0.1796341000
_diffrn_orient_matrix_UB_13      0.0804406000
_diffrn_orient_matrix_UB_21      0.1271114000
_diffrn_orient_matrix_UB_22      -0.0535262000
_diffrn_orient_matrix_UB_23      0.0367321000
_diffrn_orient_matrix_UB_31      0.0216987000
_diffrn_orient_matrix_UB_32      0.2269176000
_diffrn_orient_matrix_UB_33      0.0723493000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9246
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.723
_diffrn_reflns_theta_min         3.955
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.805
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.68a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.288
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0610P)²+0.0982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1418
_reflns_number_total             1785
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00940h2.cif
_cod_data_source_block           tp_bacidup_10_270_00
_cod_depositor_comments
'Adding full bibliography for 7247467--7247477.cif.'
_cod_original_cell_volume        902.77(6)
_cod_database_code               7247476
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C10 H10 O3'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.798
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.573
_oxdiff_exptl_absorpt_empirical_full_min 0.389
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.65981(10) 0.4934(2) 0.47687(7) 0.0838(4) Uani 1 1 d . . . . .
O1 O 0.87566(10) 0.4950(2) 0.40582(9) 0.0911(4) Uani 1 1 d . . . . .
O2 O 0.93719(13) 0.7786(3) 0.52678(11) 0.0924(4) Uani 1 1 d . . . . .
C5 C 0.51853(11) 0.3521(3) 0.33009(9) 0.0575(4) Uani 1 1 d . . . . .
C4 C 0.61530(12) 0.5162(3) 0.38766(10) 0.0601(4) Uani 1 1 d . . . . .
C6 C 0.47112(14) 0.3589(3) 0.22703(11) 0.0700(4) Uani 1 1 d . . . . .
C1 C 0.86206(14) 0.6927(3) 0.44603(13) 0.0741(5) Uani 1 1 d . . . . .
C10 C 0.47532(13) 0.1824(3) 0.38060(13) 0.0739(4) Uani 1 1 d . . . . .
C3 C 0.65865(16) 0.7117(3) 0.33398(13) 0.0764(5) Uani 1 1 d . . . . .
C7 C 0.38380(15) 0.1975(4) 0.17665(13) 0.0841(5) Uani 1 1 d . . . . .
C2 C 0.75924(18) 0.8547(4) 0.40422(17) 0.0886(6) Uani 1 1 d . . . . .
C8 C 0.34313(16) 0.0276(4) 0.22723(16) 0.0906(6) Uani 1 1 d . . . . .
C9 C 0.38845(16) 0.0198(4) 0.32935(16) 0.0891(6) Uani 1 1 d . . . . .
H2 H 1.004(2) 0.682(6) 0.548(2) 0.151(11) Uiso 1 1 d . . . . .
H3A H 0.5953(18) 0.827(4) 0.2962(15) 0.106(6) Uiso 1 1 d . . . . .
H3B H 0.6796(15) 0.619(4) 0.2854(14) 0.086(5) Uiso 1 1 d . . . . .
H6 H 0.5015(15) 0.480(3) 0.1948(13) 0.080(5) Uiso 1 1 d . . . . .
H10 H 0.5062(15) 0.189(3) 0.4501(15) 0.087(5) Uiso 1 1 d . . . . .
H7 H 0.3509(17) 0.207(4) 0.1069(16) 0.098(6) Uiso 1 1 d . . . . .
H8 H 0.279(2) -0.083(4) 0.1871(16) 0.109(7) Uiso 1 1 d . . . . .
H2A H 0.7463(17) 0.932(4) 0.4624(15) 0.097(6) Uiso 1 1 d . . . . .
H2B H 0.781(2) 0.999(5) 0.3738(16) 0.117(7) Uiso 1 1 d . . . . .
H9 H 0.360(2) -0.082(5) 0.3651(17) 0.118(8) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
6 0 3 0.1413
-6 0 -3 0.1240
4 -3 -4 0.1325
-4 3 4 0.0984
7 0 -7 0.0175
-7 0 7 0.0010
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 H2 113.0(18) . . ?
C6 C5 C4 122.28(14) . . ?
C10 C5 C4 118.99(13) . . ?
C10 C5 C6 118.72(15) . . ?
O3 C4 C5 120.75(13) . . ?
O3 C4 C3 119.87(14) . . ?
C5 C4 C3 119.38(12) . . ?
C5 C6 H6 116.6(11) . . ?
C7 C6 C5 120.25(17) . . ?
C7 C6 H6 123.2(11) . . ?
O1 C1 O2 122.24(17) . . ?
O1 C1 C2 122.76(16) . . ?
O2 C1 C2 114.98(15) . . ?
C5 C10 H10 116.7(12) . . ?
C9 C10 C5 120.56(17) . . ?
C9 C10 H10 122.7(12) . . ?
C4 C3 C2 111.80(15) . . ?
C4 C3 H3A 108.4(12) . . ?
C4 C3 H3B 106.6(11) . . ?
C2 C3 H3A 112.9(12) . . ?
C2 C3 H3B 110.0(11) . . ?
H3A C3 H3B 106.8(15) . . ?
C6 C7 H7 119.6(12) . . ?
C8 C7 C6 120.52(16) . . ?
C8 C7 H7 119.8(12) . . ?
C1 C2 C3 113.43(15) . . ?
C1 C2 H2A 106.3(12) . . ?
C1 C2 H2B 106.0(14) . . ?
C3 C2 H2A 113.8(12) . . ?
C3 C2 H2B 113.1(14) . . ?
H2A C2 H2B 103.3(17) . . ?
C7 C8 C9 119.99(18) . . ?
C7 C8 H8 117.1(12) . . ?
C9 C8 H8 122.9(12) . . ?
C10 C9 H9 117.9(15) . . ?
C8 C9 C10 119.9(2) . . ?
C8 C9 H9 122.0(15) . . ?
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
O3 C4 1.2125(17) . ?
O1 C1 1.2304(19) . ?
O2 C1 1.293(2) . ?
O2 H2 0.94(3) . ?
C5 C4 1.487(2) . ?
C5 C6 1.3912(19) . ?
C5 C10 1.387(2) . ?
C4 C3 1.508(2) . ?
C6 C7 1.378(3) . ?
C6 H6 0.952(18) . ?
C1 C2 1.495(3) . ?
C10 C9 1.381(2) . ?
C10 H10 0.937(19) . ?
C3 C2 1.515(3) . ?
C3 H3A 1.00(2) . ?
C3 H3B 0.97(2) . ?
C7 C8 1.370(3) . ?
C7 H7 0.94(2) . ?
C2 H2A 1.00(2) . ?
C2 H2B 0.96(2) . ?
C8 C9 1.378(3) . ?
C8 H8 1.00(2) . ?
C9 H9 0.91(3) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C4 C3 C2 1.3(2) . . . . ?
O1 C1 C2 C3 21.9(2) . . . . ?
O2 C1 C2 C3 -159.62(16) . . . . ?
C5 C4 C3 C2 -178.32(14) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C5 C10 C9 C8 -0.8(3) . . . . ?
C4 C5 C6 C7 177.93(14) . . . . ?
C4 C5 C10 C9 -177.38(15) . . . . ?
C4 C3 C2 C1 68.9(2) . . . . ?
C6 C5 C4 O3 -174.81(14) . . . . ?
C6 C5 C4 C3 4.8(2) . . . . ?
C6 C5 C10 C9 1.3(2) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
C10 C5 C4 O3 3.8(2) . . . . ?
C10 C5 C4 C3 -176.53(15) . . . . ?
C10 C5 C6 C7 -0.7(2) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
6.0754 -0.0008 3.4535 0.2145 0.8991 0.3815
-6.1235 0.0453 -3.3775 -0.2158 -0.9049 -0.3669
3.8935 -2.8124 -4.3058 0.1182 0.4873 -0.8652
-3.9094 2.8113 4.2942 -0.1187 -0.4897 0.8638
7.1270 -0.0252 -7.4372 -0.6682 0.6341 -0.3891
-7.1270 0.0252 7.4372 0.6682 -0.6341 0.3891
