Photochromism of phenazine-2,3-diol derivatives through excited state intermolecular proton transfer based on keto-enol tautomerization.
Ohira, Kazuki; Kozuka, Kumpei; Kaneda, Naoki; Yamamoto, Masahiro; Imato, Keiichi; Ooyama, Yousuke; Organic & biomolecular chemistry 22 (2024) 4077–4088; doi:10.1039/d4ob00387j

data_7159900
_publ_section_title
;
 Photochromism of phenazine-2,3-diol derivatives through excited state
 intermolecular proton transfer based on keto-enol tautomerization.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4077
_journal_page_last               4088
_journal_paper_doi               10.1039/d4ob00387j
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C12 H8 N2 O2'
_chemical_formula_sum            'C12 H8 N2 O2'
_chemical_formula_weight         212.20
_chemical_name_systematic        3-hydroxyphenazin-2(10H)-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2j4xxj
_audit_creation_date             2024-01-15
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2024-01-26 deposited with the CCDC.	2024-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.150(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.7817(2)
_cell_length_b                   9.7180(6)
_cell_length_c                   12.9407(6)
_cell_measurement_reflns_used    2171
_cell_measurement_temperature    299.50(18)
_cell_measurement_theta_max      31.8640
_cell_measurement_theta_min      2.6270
_cell_volume                     475.24(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.50(18)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.840
_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    -72.00   9.00   0.50    6.00    --   -5.63 -77.00-180.00  162
  2  \w    -64.00   1.00   0.50    6.00    --   -5.63 -38.00  30.00  130
  3  \w    -73.00  -2.00   0.50    6.00    --   -5.63 -38.00-120.00  142
  4  \w    -18.00  64.00   0.50    6.00    --   -5.63  57.00   0.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1806045000
_diffrn_orient_matrix_UB_12      0.0112925000
_diffrn_orient_matrix_UB_13      0.0103981000
_diffrn_orient_matrix_UB_21      -0.0430627000
_diffrn_orient_matrix_UB_22      -0.0005959000
_diffrn_orient_matrix_UB_23      -0.0538186000
_diffrn_orient_matrix_UB_31      -0.0279223000
_diffrn_orient_matrix_UB_32      -0.0720771000
_diffrn_orient_matrix_UB_33      0.0020701000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5474
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.716
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.818
_diffrn_reflns_theta_min         2.622
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.35a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       plate
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 562 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2332
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0745P)^2^+0.0017P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1294
_reflns_Friedel_coverage         0.621
_reflns_Friedel_fraction_full    0.845
_reflns_Friedel_fraction_max     0.578
_reflns_number_gt                1698
_reflns_number_total             2332
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00387j2.cif
_cod_data_source_block           exp_3245
_cod_depositor_comments
'Adding full bibliography for 7159899--7159902.cif.'
_cod_database_code               7159900
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C12H8N2O2
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.969
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              86975
_shelx_hkl_checksum              23071
_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 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.731