#------------------------------------------------------------------------------
#$Date: 2023-11-06 09:25:17 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287339 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/74/7247472.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_7247472
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
_atom_sites_solution_primary     dual
_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                 111.364(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7632(4)
_cell_length_b                   5.23201(15)
_cell_length_c                   14.4635(4)
_cell_measurement_reflns_used    5438
_cell_measurement_temperature    250.00(10)
_cell_measurement_theta_max      78.9610
_cell_measurement_theta_min      3.9520
_cell_volume                     899.46(5)
_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)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250.00(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 0.960
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  27.00   0.50    0.50    --  -49.12  19.00 -60.00  106
  2  ω   -120.00 -41.00   0.50    0.50    --  -49.12-178.00 -90.00  158
  3  ω    -26.00  27.00   0.50    0.50    --  -49.12  19.00 -30.00  106
  4  ω    -26.00  27.00   0.50    0.50    --  -49.12  19.00   0.00  106
  5  ω    -23.00 121.00   0.50    0.50    --   49.12   0.00 -90.00  288
  6  ω     62.00 120.00   0.50    0.50    --   49.12 178.00 -30.00  116
  7  ω    -43.00 -13.00   0.50    2.50    --  -88.50  38.00 -60.00   60
  8  ω    -43.00 -13.00   0.50    2.50    --  -88.50  38.00 -30.00   60
  9  ω    -43.00 -13.00   0.50    2.50    --  -88.50  38.00   0.00   60
 10  ω    -43.00 -13.00   0.50    2.50    --  -88.50  38.00  30.00   60
 11  ω    -43.00 -13.00   0.50    2.50    --  -88.50  38.00 150.00   60
 12  ω   -160.00 -73.00   0.50    2.50    --  -88.50 -57.00-150.00  174
 13  ω     38.00  66.00   0.50    2.50    --  110.00 -57.00 -90.00   56
 14  ω     97.00 178.00   0.50    2.50    --  110.00  19.00 150.00  162
 15  ω     38.00  66.00   0.50    2.50    --  110.00 -57.00 -30.00   56
 16  ω     98.00 178.00   0.50    2.50    --  110.00  38.00  30.00  160
 17  ω     38.00  66.00   0.50    2.50    --  110.00 -57.00 150.00   56
 18  ω     38.00  66.00   0.50    2.50    --  110.00 -57.00 -60.00   56
 19  ω     45.00 105.00   0.50    2.50    --  110.00 -77.00  90.00  120
 20  ω     38.00  66.00   0.50    2.50    --  110.00 -57.00   0.00   56
 21  ω     97.00 178.00   0.50    2.50    --  110.00  19.00  90.00  162
 22  ω     38.00  66.00   0.50    2.50    --  110.00 -57.00 120.00   56
 23  ω   -114.00 -25.00   0.50    0.50    --  -49.12 -77.00 -30.00  178
 24  ω     26.00 114.00   0.50    0.50    --   49.12  77.00-120.00  176
 25  ω     26.00 114.00   0.50    0.50    --   49.12  77.00  60.00  176
 26  ω     62.00 120.00   0.50    0.50    --   49.12 178.00-150.00  116
 27  ω     37.00 125.00   0.50    0.50    --   49.12  19.00  30.00  176
;
_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      0.0563490000
_diffrn_orient_matrix_UB_12      -0.1805274000
_diffrn_orient_matrix_UB_13      0.0883287000
_diffrn_orient_matrix_UB_21      0.1144159000
_diffrn_orient_matrix_UB_22      0.0420761000
_diffrn_orient_matrix_UB_23      -0.0109777000
_diffrn_orient_matrix_UB_31      0.0234650000
_diffrn_orient_matrix_UB_32      0.2286582000
_diffrn_orient_matrix_UB_33      0.0718022000
_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  0.0354
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_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            9290
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.186
_diffrn_reflns_theta_min         3.964
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.820
_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    1.316
_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         0.141
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0411
_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)+(0.0569P)²+0.0861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1196
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1566
_reflns_number_total             1875
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00940h2.cif
_cod_data_source_block           tp_bacidup_08_250_00
_cod_depositor_comments
'Adding full bibliography for 7247467--7247477.cif.'
_cod_database_code               7247472
_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
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 2.096
_oxdiff_exptl_absorpt_empirical_full_min 0.423
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 0.65946(9) 0.4940(2) 0.47685(7) 0.0807(4) Uani 1 1 d . . . . .
O1 O 0.87566(9) 0.4947(2) 0.40576(9) 0.0888(4) Uani 1 1 d . . . . .
O2 O 0.93712(11) 0.7796(2) 0.52657(9) 0.0910(4) Uani 1 1 d . . . . .
C5 C 0.51827(10) 0.3519(2) 0.32982(8) 0.0573(3) Uani 1 1 d . . . . .
C4 C 0.61497(11) 0.5163(2) 0.38753(9) 0.0594(3) Uani 1 1 d . . . . .
C6 C 0.47074(13) 0.3581(3) 0.22663(10) 0.0690(4) Uani 1 1 d . . . . .
C1 C 0.86176(13) 0.6928(3) 0.44591(11) 0.0733(4) Uani 1 1 d . . . . .
C10 C 0.47491(12) 0.1811(3) 0.38045(11) 0.0728(4) Uani 1 1 d . . . . .
C3 C 0.65840(15) 0.7121(3) 0.33368(12) 0.0762(4) Uani 1 1 d . . . . .
C7 C 0.38365(14) 0.1966(4) 0.17612(12) 0.0831(5) Uani 1 1 d . . . . .
C2 C 0.75873(16) 0.8559(3) 0.40378(16) 0.0877(5) Uani 1 1 d . . . . .
C8 C 0.34293(14) 0.0257(4) 0.22697(15) 0.0891(5) Uani 1 1 d . . . . .
C9 C 0.38834(14) 0.0176(4) 0.32933(14) 0.0880(5) Uani 1 1 d . . . . .
H2 H 1.0071(19) 0.677(4) 0.5491(16) 0.121(8) Uiso 1 1 d . . . . .
H3A H 0.5972(16) 0.827(4) 0.2961(13) 0.098(6) Uiso 1 1 d . . . . .
H3B H 0.6790(15) 0.617(4) 0.2847(14) 0.091(5) Uiso 1 1 d . . . . .
H6 H 0.5013(14) 0.475(3) 0.1952(12) 0.078(5) Uiso 1 1 d . . . . .
H10 H 0.5060(14) 0.184(3) 0.4486(13) 0.081(4) Uiso 1 1 d . . . . .
H7 H 0.3507(16) 0.206(4) 0.1067(15) 0.100(6) Uiso 1 1 d . . . . .
H8 H 0.280(2) -0.082(4) 0.1873(16) 0.119(7) Uiso 1 1 d . . . . .
H2A H 0.7458(17) 0.930(4) 0.4615(15) 0.103(6) Uiso 1 1 d . . . . .
H2B H 0.780(2) 1.007(4) 0.3717(15) 0.122(7) Uiso 1 1 d . . . . .
H9 H 0.3594(19) -0.091(5) 0.3654(15) 0.121(7) 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
2 -3 -2 0.1661
-2 3 2 0.1014
3 0 7 0.1463
-3 0 -7 0.1294
-7 0 7 0.0295
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 113.1(13) . . ?
C6 C5 C4 122.49(12) . . ?
C10 C5 C4 118.96(11) . . ?
C10 C5 C6 118.54(13) . . ?
O3 C4 C5 120.88(12) . . ?
O3 C4 C3 119.86(13) . . ?
C5 C4 C3 119.26(11) . . ?
C5 C6 H6 116.4(10) . . ?
C7 C6 C5 120.49(15) . . ?
C7 C6 H6 123.1(10) . . ?
O1 C1 O2 122.18(16) . . ?
O1 C1 C2 122.90(15) . . ?
O2 C1 C2 114.89(14) . . ?
C5 C10 H10 117.0(11) . . ?
C9 C10 C5 120.70(15) . . ?
C9 C10 H10 122.3(11) . . ?
C4 C3 C2 111.84(13) . . ?
C4 C3 H3A 109.5(11) . . ?
C4 C3 H3B 105.9(11) . . ?
C2 C3 H3A 112.2(11) . . ?
C2 C3 H3B 110.7(11) . . ?
H3A C3 H3B 106.4(14) . . ?
C6 C7 H7 119.8(12) . . ?
C8 C7 C6 120.36(15) . . ?
C8 C7 H7 119.8(12) . . ?
C1 C2 C3 113.11(14) . . ?
C1 C2 H2A 105.7(12) . . ?
C1 C2 H2B 107.2(13) . . ?
C3 C2 H2A 113.6(12) . . ?
C3 C2 H2B 112.7(13) . . ?
H2A C2 H2B 103.8(17) . . ?
C7 C8 C9 120.09(16) . . ?
C7 C8 H8 116.9(13) . . ?
C9 C8 H8 123.0(13) . . ?
C10 C9 C8 119.81(18) . . ?
C10 C9 H9 118.7(14) . . ?
C8 C9 H9 121.4(13) . . ?
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 1.2126(15) . ?
O1 C1 1.2319(17) . ?
O2 C1 1.2941(18) . ?
O2 H2 0.99(2) . ?
C5 C4 1.4864(19) . ?
C5 C6 1.3916(17) . ?
C5 C10 1.392(2) . ?
C4 C3 1.509(2) . ?
C6 C7 1.376(2) . ?
C6 H6 0.927(16) . ?
C1 C2 1.498(3) . ?
C10 C9 1.380(2) . ?
C10 H10 0.919(17) . ?
C3 C2 1.513(2) . ?
C3 H3A 0.978(19) . ?
C3 H3B 0.978(19) . ?
C7 C8 1.374(3) . ?
C7 H7 0.938(19) . ?
C2 H2A 0.99(2) . ?
C2 H2B 1.00(2) . ?
C8 C9 1.380(3) . ?
C8 H8 0.98(2) . ?
C9 H9 0.93(2) . ?
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 1.2(2) . . . . ?
O1 C1 C2 C3 22.1(2) . . . . ?
O2 C1 C2 C3 -159.86(14) . . . . ?
C5 C4 C3 C2 -178.39(13) . . . . ?
C5 C6 C7 C8 -0.4(2) . . . . ?
C5 C10 C9 C8 -1.0(3) . . . . ?
C4 C5 C6 C7 177.88(13) . . . . ?
C4 C5 C10 C9 -177.22(14) . . . . ?
C4 C3 C2 C1 68.74(19) . . . . ?
C6 C5 C4 O3 -174.87(13) . . . . ?
C6 C5 C4 C3 4.7(2) . . . . ?
C6 C5 C10 C9 1.4(2) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
C10 C5 C4 O3 3.7(2) . . . . ?
C10 C5 C4 C3 -176.69(14) . . . . ?
C10 C5 C6 C7 -0.7(2) . . . . ?
C7 C8 C9 C10 -0.2(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
2.2546 -3.2234 -2.3304 0.5031 0.1479 -0.8515
-2.3239 3.2273 2.1591 -0.5228 -0.1538 0.8384
2.7238 0.0042 7.1319 0.7827 0.2335 0.5770
-2.7371 0.0135 -7.1215 -0.7857 -0.2344 -0.5725
-7.1183 -0.0811 7.4060 0.2677 -0.8992 0.3462
7.1183 0.0811 -7.4060 -0.2677 0.8992 -0.3462
