Exploiting benzilic acid as a modular template: controlling photoreactivity and solid to liquid transition during photodimerization.
Ahsan, Mollah Rohan; Singh, Lavanya; Varma, Harshit; Mukherjee, Arijit; Chemical communications (Cambridge, England)  (2023) –; doi:10.1039/d3cc04257j

data_7132188
_publ_section_title
;
 Exploiting benzilic acid as a modular template: controlling
 photoreactivity and solid to liquid transition during photodimerization.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d3cc04257j
_journal_year                    2023
_chemical_formula_moiety         'C14 H11 O3, C13 H11 Cl N'
_chemical_formula_sum            'C27 H22 Cl N O3'
_chemical_formula_weight         443.90
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-07-31
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-08-21 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                88.6790(10)
_cell_angle_beta                 74.542(2)
_cell_angle_gamma                82.8740(10)
_cell_formula_units_Z            2
_cell_length_a                   8.5593(2)
_cell_length_b                   10.3705(2)
_cell_length_c                   13.0745(2)
_cell_measurement_reflns_used    7780
_cell_measurement_temperature    140
_cell_measurement_theta_max      79.4190
_cell_measurement_theta_min      4.2790
_cell_volume                     1109.87(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      140
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     22.00  89.00   0.50    0.61    --    0.00  37.00 -60.00  134
  2  \w    -28.00  15.00   0.50    0.61    --    0.00 -57.00-150.00   86
  3  \w    -88.00 -46.00   0.50    0.61    --    0.00 -57.00  60.00   84
  4  \w    -35.00  22.00   0.50    0.61    --    0.00 -57.00  60.00  114
  5  \w    -26.00  19.00   0.50    0.61    --    0.00 -37.00 -30.00   90
  6  \w    -87.00 -38.00   0.50    0.61    --    0.00 -57.00-150.00   98
  7  \w     77.00 139.00   0.50    3.00    --  107.20 -82.00 -60.00  124
  8  \w     84.00 195.00   0.50    3.00    --  107.20  15.00  90.00  222
  9  \w     20.00 138.00   0.50    3.00    --  107.20 -82.00-120.00  236
 10  \w     24.00  74.00   0.50    3.00    --  107.20 -82.00 -30.00  100
 11  \w     18.00  87.00   0.50    3.00    --  107.20 -61.00-180.00  138
 12  \w     25.00  73.00   0.50    3.00    --  107.20 -82.00 -60.00   96
 13  \w     26.00  88.00   0.50    3.00    --  107.20 -45.00  90.00  124
 14  \w     18.00 123.00   0.50    3.00    --  107.20 -82.00 150.00  210
 15  \w     81.00 107.00   0.50    3.00    --  107.20 -82.00  30.00   52
 16  \w    143.00 191.00   0.50    3.00    --  107.20  30.00  30.00   96
 17  \w     97.00 138.00   0.50    3.00    --  107.20  30.00  30.00   82
 18  \w    105.00 191.00   0.50    3.00    --  107.20  45.00 -30.00  172
 19  \w     19.00  90.00   0.50    3.00    --  107.20 -61.00  90.00  142
 20  \w     80.00 108.00   0.50    3.00    --  107.20 -82.00  90.00   56
 21  \w     21.00 120.00   0.50    3.00    --  107.20 -30.00 -30.00  198
 22  \w     80.00 137.00   0.50    3.00    --  107.20 -82.00 -30.00  114
 23  \w     19.00 110.00   0.50    3.00    --  107.20 -30.00-120.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0071742000
_diffrn_orient_matrix_UB_12      -0.0692923000
_diffrn_orient_matrix_UB_13      -0.1044121000
_diffrn_orient_matrix_UB_21      0.1666577000
_diffrn_orient_matrix_UB_22      -0.0749164000
_diffrn_orient_matrix_UB_23      0.0010210000
_diffrn_orient_matrix_UB_31      -0.0870439000
_diffrn_orient_matrix_UB_32      -0.1095493000
_diffrn_orient_matrix_UB_33      0.0635944000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12330
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.754
_diffrn_reflns_theta_min         4.297
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.760
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0396
_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/[\s^2^(Fo^2^)+(0.0474P)^2^+0.3568P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4256
_reflns_number_total             4648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04257j2.cif
_cod_data_source_block           exp_1320_am-r-135-acn
_cod_database_code               7132188
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.844
_shelx_estimated_absorpt_t_min   0.720
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C25(H25), C23(H23), C28(H28), C24(H24), C9(H9), C21(H21), C13(H13),
 C15(H15), C20(H20), C26(H26), C16(H16), C18(H18), C17(H17), C12(H12), C30(H30),
  C32(H32), C11(H11), C10(H10), C31(H31)
;
_shelx_res_checksum              24433
_shelx_hkl_checksum              76846
_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 2.460
_oxdiff_exptl_absorpt_empirical_full_min 0.719