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_7232392
_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 N3 O4'
_chemical_formula_sum            'C12 H9 N3 O4'
_chemical_formula_weight         259.22
_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             2018-09-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-02 deposited with the CCDC.    2019-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.493(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8236(6)
_cell_length_b                   8.6618(3)
_cell_length_c                   12.0259(6)
_cell_measurement_reflns_used    3636
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      32.8530
_cell_measurement_theta_min      2.9540
_cell_volume                     1129.53(10)
_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 -90.00  624
  2  \w    -69.00 103.50   0.30   20.00    --   29.89  54.00 150.00  575
;
_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      0.0340830000
_diffrn_orient_matrix_UB_12      -0.0072679000
_diffrn_orient_matrix_UB_13      -0.0367066000
_diffrn_orient_matrix_UB_21      0.0456720000
_diffrn_orient_matrix_UB_22      -0.0431187000
_diffrn_orient_matrix_UB_23      0.0464707000
_diffrn_orient_matrix_UB_31      -0.0320900000
_diffrn_orient_matrix_UB_32      -0.0692311000
_diffrn_orient_matrix_UB_33      -0.0251285000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6344
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.985
_diffrn_reflns_theta_max         24.985
_diffrn_reflns_theta_min         2.990
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72311
_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    1.524
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         1984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0524P)^2^+0.4059P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1779
_reflns_number_total             1984
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce01878b2.cif
_cod_data_source_block           rx4_etoh_100k
_cod_depositor_comments
'Adding full bibliography for 7232391--7232396.cif.'
_cod_database_code               7232392
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C12 H10 N3 O4'
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.952
_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), C5(H5), C8(H8), C2(H2B), C9(H9), C10(H10), C11(H11)
;
_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 1.185
_oxdiff_exptl_absorpt_empirical_full_min 0.904