Fluorescence Behavior of Bis(cyanostyryl)pyrrole Derivatives Depending on the Substituent Position of Cyano Groups in Solution and in Solid State.
Yokoyama, Soichi; Nishiwaki, Nagatoshi; The Journal of organic chemistry 84 (2019) 1192–1200; doi:10.1021/acs.joc.8b02517

data_4036036
_publ_section_title
;
 Fluorescence Behavior of Bis(cyanostyryl)pyrrole Derivatives Depending on
 the Substituent Position of Cyano Groups in Solution and in Solid State.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1192
_journal_page_last               1200
_journal_paper_doi               10.1021/acs.joc.8b02517
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C22 H15 N3'
_chemical_formula_sum            'C22 H15 N3'
_chemical_formula_weight         321.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2bc 2'
_space_group_name_H-M_alt        'P 2 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-09
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.64100(13)
_cell_length_b                   13.2241(3)
_cell_length_c                   27.0020(7)
_cell_measurement_reflns_used    5154
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4590
_cell_measurement_theta_min      3.6770
_cell_volume                     1657.20(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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     42.00 120.00   0.50    3.59    --   42.80  36.00  22.00  156
  2  \w     48.00  85.00   0.50   14.36    --   76.50 -36.00-133.00   74
  3  \w     51.00  77.00   0.50   14.36    --   76.50 -85.00  73.00   52
  4  \w    -95.00 -10.00   0.50    3.59    --  -42.80 125.00-180.00  170
  5  \w    -69.00 -33.00   0.50   14.36    -- -106.00  57.00 -90.00   72
  6  \w    -75.00 -46.00   0.50   14.36    -- -106.00 125.00 -60.00   58
  7  \w   -109.00 -71.00   0.50   14.36    -- -106.00 125.00  30.00   76
  8  \w   -106.00 -80.00   0.50   14.36    -- -106.00  77.00   0.00   52
  9  \w   -107.00 -81.00   0.50   14.36    -- -106.00  57.00 -60.00   52
 10  \w   -119.00 -92.00   0.50   14.36    -- -106.00  57.00 -90.00   54
 11  \w   -120.00 -32.00   0.50   14.36    -- -106.00 125.00   0.00  176
 12  \w    -74.00 -49.00   0.50   14.36    -- -106.00 125.00 120.00   50
 13  \w    -79.00 -32.00   0.50   14.36    -- -106.00 125.00 150.00   94
 14  \w   -101.00 -76.00   0.50   14.36    -- -106.00 125.00 120.00   50
 15  \w   -177.00-136.00   0.50   14.36    -- -106.00 -19.00  90.00   82
 16  \w   -110.00 -84.00   0.50   14.36    -- -106.00 -19.00  90.00   52
 17  \w   -113.00 -88.00   0.50   14.36    -- -106.00 -37.00 120.00   50
 18  \w   -143.00-117.00   0.50   14.36    -- -106.00-126.00   3.00   52
 19  \w   -152.00-127.00   0.50   14.36    -- -106.00 -99.00 -90.00   50
 20  \w   -142.00 -98.00   0.50   14.36    -- -106.00 -36.00-133.00   88
 21  \w   -101.00 -73.00   0.50    3.59    --  -42.80 -57.00 -90.00   56
 22  \w   -176.00-127.00   0.50   14.36    -- -106.00 -37.00 120.00   98
 23  \w   -122.00 -83.00   0.50   14.36    -- -106.00  77.00-180.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2039294000
_diffrn_orient_matrix_UB_12      -0.0302362000
_diffrn_orient_matrix_UB_13      -0.0425044000
_diffrn_orient_matrix_UB_21      -0.2138257000
_diffrn_orient_matrix_UB_22      0.0443994000
_diffrn_orient_matrix_UB_23      -0.0378634000
_diffrn_orient_matrix_UB_31      0.1512167000
_diffrn_orient_matrix_UB_32      0.1033814000
_diffrn_orient_matrix_UB_33      0.0038493000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            9457
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.194
_diffrn_reflns_theta_min         3.273
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1126 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0583P)^2^+0.4622P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.616
_reflns_Friedel_fraction_full    0.943
_reflns_Friedel_fraction_max     0.896
_reflns_number_gt                3098
_reflns_number_total             3225
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02517_si_002.cif
_cod_data_source_block           180409compd1
_cod_original_cell_volume        1657.19(7)
_cod_database_code               4036036
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C22 H15 N3'
_diffrn_oxdiff_ac3_digest_frames
;
01daf9d468c14ff4458924b9ba088403d0017920dff
;
_diffrn_oxdiff_ac3_digest_hkl
;
010d68251cb037997ab232541cb4eecb1a8a70
;
_reflns_odcompleteness_completeness 98.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C6(H6), C23(H23), C9(H9), C12(H12), C22(H22), C4(H4),
 C19(H19), C10(H10), C13(H13), C3(H3), C20(H20), C21(H21), C11(H11)
;
_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 2.252
_oxdiff_exptl_absorpt_empirical_full_min 0.791