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_7132190
_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         'C13 H10 Br N'
_chemical_formula_sum            'C13 H10 Br N'
_chemical_formula_weight         260.13
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-28
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-08-28 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3605(4)
_cell_length_b                   12.2746(4)
_cell_length_c                   12.3726(3)
_cell_measurement_reflns_used    1466
_cell_measurement_temperature    295
_cell_measurement_theta_max      74.9330
_cell_measurement_theta_min      5.0400
_cell_volume                     1117.83(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      295
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.964
_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    -19.00  12.00   0.50    0.50    --    0.00  37.00  30.00   62
  2  \w     41.00  86.00   0.50    0.50    --    0.00  37.00  30.00   90
  3  \w     59.00  86.00   0.50    0.50    --    0.00  57.00 150.00   54
  4  \w     19.00  47.00   0.50    3.00    --  107.20 -30.00  30.00   56
  5  \w    111.00 197.00   0.50    3.00    --  107.20  77.00  60.00  172
  6  \w     77.00 102.00   0.50    3.00    --  107.20  77.00  60.00   50
  7  \w     90.00 115.00   0.50    3.00    --  107.20  30.00 -60.00   50
  8  \w     63.00 124.00   0.50    3.00    --  107.20 -30.00  30.00  122
  9  \w    120.00 191.00   0.50    3.00    --  107.20  30.00 -60.00  142
 10  \w     58.00 127.00   0.50    3.00    --  107.20 -30.00 -90.00  138
;
_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      0.0487695000
_diffrn_orient_matrix_UB_12      -0.0964427000
_diffrn_orient_matrix_UB_13      -0.0742277000
_diffrn_orient_matrix_UB_21      -0.1198348000
_diffrn_orient_matrix_UB_22      0.0486040000
_diffrn_orient_matrix_UB_23      -0.0899888000
_diffrn_orient_matrix_UB_31      0.1644674000
_diffrn_orient_matrix_UB_32      0.0640276000
_diffrn_orient_matrix_UB_33      -0.0434979000
_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  0.0445
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3788
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.905
_diffrn_reflns_theta_min         5.076
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.705
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52328
_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    1.546
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 434 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2153
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0554
_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^)+(0.1030P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.1832
_reflns_Friedel_coverage         0.564
_reflns_Friedel_fraction_full    0.848
_reflns_Friedel_fraction_max     0.759
_reflns_number_gt                1510
_reflns_number_total             2153
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04257j2.cif
_cod_data_source_block           exp_1412-am-r-3brstp
_cod_database_code               7132190
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.453
_shelx_estimated_absorpt_t_min   0.333
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C6(H6), C15(H15), C8(H8), C11(H11), C9(H9), C7(H7), C12(H12),
 C4(H4), C3(H3)
;
_shelx_res_checksum              77869
_shelx_hkl_checksum              61146
_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 2.430
_oxdiff_exptl_absorpt_empirical_full_min 0.397