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_7132186
_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 H10 N'
_chemical_formula_sum            'C27 H21 N O3'
_chemical_formula_weight         407.45
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-11
_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                93.589(2)
_cell_angle_beta                 94.776(2)
_cell_angle_gamma                99.891(2)
_cell_formula_units_Z            4
_cell_length_a                   6.7453(2)
_cell_length_b                   16.8984(3)
_cell_length_c                   18.0463(4)
_cell_measurement_reflns_used    6754
_cell_measurement_temperature    140
_cell_measurement_theta_max      79.1540
_cell_measurement_theta_min      4.9510
_cell_volume                     2013.19(8)
_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      140.00
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.966
_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    -89.00 -15.00   0.50    0.50    --    0.00 -57.00-150.00  148
  2  \w     17.00  43.00   0.50    0.50    --    0.00  37.00-180.00   52
  3  \w    -89.00 -33.00   0.50    0.50    --    0.00 -37.00 -30.00  112
  4  \w     22.00  89.00   0.50    0.50    --    0.00  37.00  90.00  134
  5  \w    -11.00  15.00   0.50    0.50    --    0.00 -57.00-150.00   52
  6  \w    -29.00  47.00   0.50    0.50    --    0.00  82.00 -90.00  152
  7  \w     56.00  87.00   0.50    0.50    --    0.00  82.00 -90.00   62
  8  \w     25.00 126.00   0.50    0.60    --  107.20 -61.00 150.00  202
  9  \w     80.00 192.00   0.50    0.60    --  107.20  15.00 -90.00  224
 10  \w     61.00  87.00   0.50    0.60    --  107.20 -45.00 -30.00   52
 11  \w     88.00 114.00   0.50    0.60    --  107.20 -82.00 -60.00   52
 12  \w     27.00  53.00   0.50    0.60    --  107.20 -82.00  90.00   52
 13  \w     77.00 140.00   0.50    0.60    --  107.20 -82.00  90.00  126
 14  \w     20.00  62.00   0.50    0.60    --  107.20 -30.00-120.00   84
 15  \w     41.00  75.00   0.50    0.60    --  107.20 -82.00 -60.00   68
 16  \w     89.00 197.00   0.50    0.60    --  107.20  30.00-150.00  216
 17  \w     33.00  98.00   0.50    0.60    --  107.20 -15.00-120.00  130
 18  \w     61.00 132.00   0.50    0.60    --  107.20 -61.00   0.00  142
 19  \w     88.00 140.00   0.50    0.60    --  107.20 -82.00-150.00  104
 20  \w     87.00 196.00   0.50    0.60    --  107.20  45.00 150.00  218
 21  \w     28.00  54.00   0.50    0.60    --  107.20 -61.00   0.00   52
 22  \w     43.00 139.00   0.50    0.60    --  107.20 -82.00   0.00  192
 23  \w     61.00 110.00   0.50    0.60    --  107.20 -30.00 120.00   98
 24  \w     86.00 114.00   0.50    0.60    --  107.20 -82.00  30.00   56
 25  \w     79.00 110.00   0.50    0.60    --  107.20 -82.00-120.00   62
 26  \w     74.00 121.00   0.50    0.60    --  107.20 -30.00-120.00   94
 27  \w     21.00 138.00   0.50    0.60    --  107.20 -82.00 150.00  234
;
_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      -0.1006914000
_diffrn_orient_matrix_UB_12      -0.0621899000
_diffrn_orient_matrix_UB_13      -0.0640397000
_diffrn_orient_matrix_UB_21      -0.1885775000
_diffrn_orient_matrix_UB_22      -0.0195834000
_diffrn_orient_matrix_UB_23      0.0427466000
_diffrn_orient_matrix_UB_31      -0.0924370000
_diffrn_orient_matrix_UB_32      0.0660736000
_diffrn_orient_matrix_UB_33      -0.0381498000
_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  0.0527
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23775
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.662
_diffrn_reflns_theta_min         4.934
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50413
_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    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0012(2)
_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   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     576
_refine_ls_number_reflns         8483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0690P)^2^+0.1399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1477
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6467
_reflns_number_total             8483
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04257j2.cif
_cod_data_source_block           exp_1357-am-l-284-etoh
_cod_database_code               7132186
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.873
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C57(H57), C39(H39), C49(H49), C62(H62), C61(H61), C52(H52), C60(H60),
 C17(H17), C59(H59), C44(H44), C48(H48), C40(H40), C31(H31), C19(H19), C33(H33),
  C37(H37), C46(H46), C16(H16), C42(H42), C13(H13), C27(H27), C53(H53),
 C55(H55), C47(H47), C41(H41), C54(H54), C29(H29), C14(H14), C30(H30), C23(H23),
  C15(H15), C20(H20), C28(H28), C34(H34), C22(H22), C21(H21), C36(H36), C35(H35)
;
_shelx_res_checksum              63587
_shelx_hkl_checksum              79872
_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 2.078
_oxdiff_exptl_absorpt_empirical_full_min 0.570