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_7232391
_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 Cl N2 O2, C4 H9 N O'
_chemical_formula_sum            'C16 H18 Cl N3 O3'
_chemical_formula_weight         335.78
_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     iterative
_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                90.615(5)
_cell_angle_beta                 94.232(4)
_cell_angle_gamma                107.982(5)
_cell_formula_units_Z            2
_cell_length_a                   7.0839(3)
_cell_length_b                   10.8648(6)
_cell_length_c                   10.9553(6)
_cell_measurement_reflns_used    4259
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      32.6280
_cell_measurement_theta_min      3.0160
_cell_volume                     799.30(7)
_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    'olex2.solve (Bourhis et al., 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   15.00    --   29.89  54.00-120.00  624
  2  \w    -69.00 118.20   0.30   15.00    --   29.89  54.00  60.00  624
  3  \w    -69.00 118.20   0.30   15.00    --   29.89  54.00  60.00  624
  4  \w    -65.00 118.00   0.30   15.00    --   29.89  54.00   0.00  610
;
_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      -0.0937886000
_diffrn_orient_matrix_UB_12      0.0101359000
_diffrn_orient_matrix_UB_13      0.0030945000
_diffrn_orient_matrix_UB_21      -0.0485245000
_diffrn_orient_matrix_UB_22      -0.0665713000
_diffrn_orient_matrix_UB_23      -0.0147183000
_diffrn_orient_matrix_UB_31      0.0020940000
_diffrn_orient_matrix_UB_32      -0.0135057000
_diffrn_orient_matrix_UB_33      0.0631977000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0224
_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       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9552
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         2.666
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74600
_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    1.395
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.066
_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     219
_refine_ls_number_reflns         2799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0776P)^2^+0.3610P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1368
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2457
_reflns_number_total             2799
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce01878b2.cif
_cod_data_source_block           19dmf_100k
_cod_depositor_comments
'Adding full bibliography for 7232391--7232396.cif.'
_cod_database_code               7232391
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C12 H10 N2 O2 Cl1'
_chemical_oxdiff_usercomment     '0.3 mm loop'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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:
 C2(H2A), C12(H12), C5(H5), C4(H4), C9(H9), C11(H11), C10(H10)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_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 1.216
_oxdiff_exptl_absorpt_empirical_full_min 0.879