Novel π-extended hybrid xanthene dyes with two spirolactone rings for optoelectronic and biological applications.
Wang, Qing; Jiao, Xiaojie; Liu, Chang; Huang, Kun; He, Song; Zhao, Liancheng; Zeng, Xianshun; Organic & biomolecular chemistry 16 (2018) 7609–7618; doi:10.1039/c8ob01671b

data_7156451
_publ_section_title
;
 Novel \p-extended hybrid xanthene dyes with two spirolactone rings for
 optoelectronic and biological applications.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7609
_journal_page_last               7618
_journal_paper_doi               10.1039/c8ob01671b
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C42 H29 N O7'
_chemical_formula_sum            'C42 H29 N O7'
_chemical_formula_weight         659.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc20926m
_audit_creation_date             2018-09-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-20 deposited with the CCDC.
2018-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.197(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6280(4)
_cell_length_b                   12.0003(3)
_cell_length_c                   26.2562(8)
_cell_measurement_reflns_used    7784
_cell_measurement_temperature    299.68(10)
_cell_measurement_theta_max      73.4330
_cell_measurement_theta_min      4.9820
_cell_volume                     3955.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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      air
_diffrn_ambient_temperature      299.68(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.942
_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    -30.00   1.00   0.50    1.00    --    0.00 -38.00 -60.00   62
  2  \w    -59.00 -18.00   0.50    1.00    --    0.00 -38.00  30.00   82
  3  \w    -79.00 -50.00   0.50    1.00    --    0.00 -38.00 -60.00   58
  4  \w    -30.00  88.00   0.50    1.00    --    0.00  82.00 -30.00  236
  5  \w    -26.00   0.00   0.50    1.00    --    0.00  -6.00 110.00   52
  6  \w     63.00 103.00   0.50    4.00    --   94.60 -82.00 -30.00   80
  7  \w      5.00  31.00   0.50    4.00    --   94.60 -82.00   0.00   52
  8  \w     76.00 117.00   0.50    4.00    --   94.60  45.00   0.00   82
  9  \w      6.00  71.00   0.50    4.00    --   94.60 -30.00 150.00  130
 10  \w    153.00 179.00   0.50    4.00    --   94.60  45.00   0.00   52
 11  \w     78.00 112.00   0.50    4.00    --   94.60 -82.00 -90.00   68
 12  \w     55.00 106.00   0.50    4.00    --   94.60 -30.00-150.00  102
 13  \w      6.00  49.00   0.50    4.00    --   94.60 -30.00-150.00   86
 14  \w     45.00 125.00   0.50    4.00    --   94.60 -82.00   0.00  160
 15  \w     14.00 118.00   0.50    4.00    --   94.60 -15.00-150.00  208
 16  \w     14.00 118.00   0.50    4.00    --   94.60 -61.00   0.00  208
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0093433000
_diffrn_orient_matrix_UB_12      0.0097442000
_diffrn_orient_matrix_UB_13      -0.0588277000
_diffrn_orient_matrix_UB_21      -0.1222769000
_diffrn_orient_matrix_UB_22      0.0025753000
_diffrn_orient_matrix_UB_23      -0.0018023000
_diffrn_orient_matrix_UB_31      0.0033368000
_diffrn_orient_matrix_UB_32      0.1280000000
_diffrn_orient_matrix_UB_33      0.0045342000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            21933
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.923
_diffrn_reflns_theta_min         3.683
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.616
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.771
_refine_diff_density_min         -0.810
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         7557
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0974
_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^)+(0.1961P)^2^+1.2135P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2989
_refine_ls_wR_factor_ref         0.3150
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5481
_reflns_number_total             7557
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01671b2.cif
_cod_data_source_block           wq
_cod_depositor_comments          'Adding full bibliography for 7156451.cif.'
_cod_database_code               7156451
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.813
_reflns_odcompleteness_completeness 99.76
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C3A-C4A = C3-C4
 1.53 with sigma of 0.01
 C1-N1 = C1-N1A = N1-C3 = N1A-C3A
 1.48 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C3) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C4A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N1) \\sim Ueq, Uanis(N1A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N1) = Uanis(N1A)
Uanis(C3) = Uanis(C3A) = Uanis(C4) = Uanis(C4A)
4. Others
 Sof(H1BD)=Sof(H1BE)=Sof(C3A)=Sof(C4A)=1-FVAR(1)
 Sof(H1AB)=Sof(H1AC)=Sof(C3)=Sof(C4)=FVAR(1)
 Sof(N1A)=1-FVAR(2)
 Sof(N1)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1AB,H1AC), C1(H1BD,H1BE), C3(H3A,H3B)
5.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C1AA(H1AA), C23(H23), C28(H28), C7(H7A), C27(H27), C6(H6), C30(H30),
  C41(H41), C13(H13), C33(H33), C32(H32), C40(H40), C14(H14), C39(H39),
 C38(H38), C16(H16), C15(H15)
5.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C4(H4A,H4B,H4C)
5.d Idealised tetrahedral OH refined as rotating group:
 O7(H7)
;
_shelx_res_checksum              46494
_shelx_fab_checksum              8872
_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 1.346
_oxdiff_exptl_absorpt_empirical_full_min 0.721