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_7232393
_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         'C13 H9 N3 O2, C3 H7 N O'
_chemical_formula_sum            'C16 H16 N4 O3'
_chemical_formula_weight         312.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-02
_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                105.738(2)
_cell_angle_beta                 94.770(2)
_cell_angle_gamma                103.820(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0323(3)
_cell_length_b                   8.6204(4)
_cell_length_c                   13.7182(6)
_cell_measurement_reflns_used    5882
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.55
_cell_volume                     767.47(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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_temperature      100.0(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10582
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.562
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0383 before and 0.0307 after correction. The Ratio of minimum to maximum transmission is 0.9504. The \l/2 correction factor is 0.00150.'
_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    1.352
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0324
_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^)+(0.0625P)^2^+0.1256P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.1020
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2416
_reflns_number_total             2711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce01878b2.cif
_cod_data_source_block           dd16_100k_0m
_cod_depositor_comments
'Adding full bibliography for 7232391--7232396.cif.'
_cod_database_code               7232393
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.943
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C14(H14), C3(H3), C4(H4), C6(H6), C5(H5), C12(H12)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'