A water-soluble pyrazino[2,3-g]quinoxaline photosensitizer for high-efficiency one- and two-photon excited bioimaging and photodynamic therapy.
Zhang, Li-Peng; Li, Xianqiang; Liu, Tianlong; Kang, Lin; Huang, Xing; Zhao, Yuxia; Chemical communications (Cambridge, England) 56 (2020) 5544–5547; doi:10.1039/d0cc02285c

data_7126336
_publ_section_title
;
 A water-soluble pyrazino[2,3-g]quinoxaline photosensitizer for
 high-efficiency one- and two-photon excited bioimaging and photodynamic
 therapy.
;
_journal_issue                   41
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5544
_journal_page_last               5547
_journal_paper_doi               10.1039/d0cc02285c
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         '2(C25 H29 N4), C H2 Cl2'
_chemical_formula_sum            'C51 H60 Cl2 N8'
_chemical_formula_weight         855.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2020-01-03 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.159(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.9296(6)
_cell_length_b                   9.8470(3)
_cell_length_c                   22.4505(7)
_cell_measurement_reflns_used    10033
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.0730
_cell_measurement_theta_min      4.1580
_cell_volume                     4579.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_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   -111.00 -14.00   1.00    1.10    --  -39.74 -57.00  60.00   97
  2  \w    -67.00  21.00   1.00    1.10    --  -39.74  77.00-150.00   88
  3  \w    -47.00  -4.00   1.00    1.10    --   39.74   0.00 -90.00   43
  4  \w     34.00 117.00   1.00    5.00    --  107.19 -45.00-120.00   83
  5  \w     27.00 109.00   1.00    5.00    --  107.19 -94.00 -90.00   82
  6  \w     76.00 177.00   1.00    5.00    --  107.19  77.00 150.00  101
  7  \w     25.00  54.00   1.00    5.00    --  107.19 -94.00-150.00   29
  8  \w     34.00 130.00   1.00    5.00    --  107.19 -77.00  60.00   96
  9  \w     27.00  52.00   1.00    5.00    --  107.19 -94.00  90.00   25
 10  \w     39.00 106.00   1.00    5.00    --  107.19-125.00 -90.00   67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0712263000
_diffrn_orient_matrix_UB_12      0.0447128000
_diffrn_orient_matrix_UB_13      0.0203891000
_diffrn_orient_matrix_UB_21      0.0182129000
_diffrn_orient_matrix_UB_22      -0.1374741000
_diffrn_orient_matrix_UB_23      -0.0224562000
_diffrn_orient_matrix_UB_31      -0.0110631000
_diffrn_orient_matrix_UB_32      0.0601992000
_diffrn_orient_matrix_UB_33      -0.0659681000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18686
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.291
_diffrn_reflns_theta_min         4.012
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.954
_refine_diff_density_min         -1.381
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     610
_refine_ls_number_reflns         8976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0894
_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^)+(0.1307P)^2^+11.6350P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2619
_refine_ls_wR_factor_ref         0.2672
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8128
_reflns_number_total             8976
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc02285c2.cif
_cod_data_source_block           20180523d
_cod_depositor_comments          'Adding full bibliography for 7126336.cif.'
_cod_database_code               7126336
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C1H1N1
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C51) = Uanis(C51A)
3. Others
 Sof(C47A)=Sof(H47C)=Sof(H47D)=Sof(C48A)=Sof(H48D)=Sof(H48E)=Sof(H48F)=
 Sof(C49A)=Sof(H49C)=Sof(H49D)=Sof(C50A)=Sof(H50D)=Sof(H50E)=Sof(H50F)=Sof(N8A)=
 1-FVAR(1)
 Sof(C47)=Sof(H47A)=Sof(H47B)=Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(H48C)=Sof(C49)=
 Sof(H49A)=Sof(H49B)=Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(H50C)=Sof(N8)=FVAR(1)
 Sof(C51A)=Sof(H51C)=Sof(H51D)=1-FVAR(2)
 Sof(C51)=Sof(H51A)=Sof(H51B)=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C22(H22A,H22B), C24(H24A,H24B), C27(H27A,H27B),
 C29(H29A,H29B), C47(H47A,H47B), C49(H49A,H49B), C47A(H47C,H47D), C49A(H49C,
 H49D), C51(H51A,H51B), C51A(H51C,H51D)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C13(H13), C17(H17), C18(H18), C20(H20),
 C21(H21), C31(H31), C32(H32), C34(H34), C35(H35), C38(H38), C42(H42), C43(H43),
  C45(H45), C46(H46)
4.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C),
 C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C48(H48A,H48B,H48C), C50(H50A,H50B,
 H50C), C48A(H48D,H48E,H48F), C50A(H50D,H50E,H50F)
;
_shelx_res_checksum              19995
_shelx_hkl_checksum              99644
_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 1.428
_oxdiff_exptl_absorpt_empirical_full_min 0.341