Water-assisted ground state intra-molecular proton transfer in 2,5-dihydroxy-substituted azobenzenes: experimental and computational studies
Das, Dhiraj; Roy Choudhury, Angshuman; CrystEngComm 21 (2019) 2373–; doi:10.1039/C8CE01878B

data_7232394
_publ_section_title
;
 Water-assisted ground state intra-molecular proton transfer in
 2,5-dihydroxy-substituted azobenzenes: experimental and computational
 studies
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              2373
_journal_paper_doi               10.1039/C8CE01878B
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C12 H9 Br N2 O2, H2 O'
_chemical_formula_sum            'C12 H11 Br N2 O3'
_chemical_formula_weight         311.14
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-04 deposited with the CCDC.    2019-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.737(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.93930(10)
_cell_length_b                   13.8586(4)
_cell_length_c                   21.9545(7)
_cell_measurement_reflns_used    3808
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      32.8440
_cell_measurement_theta_min      3.0410
_cell_volume                     1196.02(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -69.00 118.20   0.30   20.00    --   29.89  54.00-180.00  624
  2  \w    -69.00 118.20   0.30   20.00    --   29.89  54.00 -60.00  624
  3  \w    -69.00  20.10   0.30   20.00    --   29.89  54.00  60.00  297
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0112007000
_diffrn_orient_matrix_UB_12      0.0507143000
_diffrn_orient_matrix_UB_13      -0.0040534000
_diffrn_orient_matrix_UB_21      -0.0707313000
_diffrn_orient_matrix_UB_22      -0.0069817000
_diffrn_orient_matrix_UB_23      -0.0302272000
_diffrn_orient_matrix_UB_31      -0.1655726000
_diffrn_orient_matrix_UB_32      -0.0004454000
_diffrn_orient_matrix_UB_33      0.0108699000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8806
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.940
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.439
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.807
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0309
_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^)+(0.0318P)^2^+1.6498P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0761
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1881
_reflns_number_total             2110
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce01878b2.cif
_cod_data_source_block           dd-100k
_cod_depositor_comments
'Adding full bibliography for 7232391--7232396.cif.'
_cod_database_code               7232394
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_usercomment     '0.2 mm loop'
_shelx_estimated_absorpt_t_max   0.683
_shelx_estimated_absorpt_t_min   0.546
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C5(H5), C12(H12), C11(H11), C9(H9)
;
_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 1.283
_oxdiff_exptl_absorpt_empirical_full_min 0.876