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_4036037
_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      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
_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                 99.139(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4693(3)
_cell_length_b                   12.8715(2)
_cell_length_c                   9.0715(2)
_cell_measurement_reflns_used    7586
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1680
_cell_measurement_theta_min      4.5920
_cell_volume                     1668.04(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.992
_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    -66.00  21.00   0.50    0.22    --  -42.80  65.00 -42.00  174
  2  \w    -57.00 -32.00   0.50    0.89    -- -106.00  65.00 -42.00   50
  3  \w    -67.00 -29.00   0.50    0.89    -- -106.00  37.00 -30.00   76
  4  \w    -73.00 -33.00   0.50    0.89    -- -106.00  37.00  90.00   80
  5  \w    -92.00 -33.00   0.50    0.89    -- -106.00  57.00  30.00  118
  6  \w    -79.00 -33.00   0.50    0.89    -- -106.00 125.00   0.00   92
  7  \w    -73.00 -47.00   0.50    0.89    -- -106.00 125.00-120.00   52
  8  \w    -83.00 -32.00   0.50    0.89    -- -106.00 125.00-180.00  102
  9  \w   -109.00 -84.00   0.50    0.89    -- -106.00  65.00 -42.00   50
 10  \w   -124.00 -81.00   0.50    0.89    -- -106.00  37.00 -30.00   86
 11  \w   -107.00 -82.00   0.50    0.89    -- -106.00 -19.00  30.00   50
 12  \w   -129.00 -90.00   0.50    0.89    -- -106.00 -37.00 120.00   78
 13  \w   -121.00 -84.00   0.50    0.89    -- -106.00 -99.00 120.00   74
 14  \w   -149.00-122.00   0.50    0.89    -- -106.00 -57.00  60.00   54
 15  \w   -160.00-117.00   0.50    0.89    -- -106.00 -57.00  30.00   86
 16  \w   -172.00-145.00   0.50    0.89    -- -106.00 -99.00 -60.00   54
 17  \w   -159.00-133.00   0.50    0.89    -- -106.00-125.00 -60.00   52
 18  \w   -129.00-104.00   0.50    0.89    -- -106.00-125.00 -60.00   50
 19  \w   -123.00 -83.00   0.50    0.89    -- -106.00 -99.00 -90.00   80
 20  \w   -119.00 -87.00   0.50    0.89    -- -106.00 -99.00 -60.00   64
 21  \w   -115.00 -19.00   0.50    0.22    --  -42.80 -65.00-178.00  192
 22  \w     83.00 113.00   0.50    0.22    --   42.80 125.00-150.00   60
 23  \w     71.00 108.00   0.50    0.22    --   42.80 125.00-180.00   74
 24  \w     51.00  76.00   0.50    0.89    --   76.50 -65.00-178.00   50
 25  \w   -120.00 -95.00   0.50    0.89    -- -106.00 125.00   0.00   50
 26  \w   -110.00 -50.00   0.50    0.89    -- -106.00 125.00 -30.00  120
 27  \w   -114.00 -88.00   0.50    0.89    -- -106.00  77.00  60.00   52
 28  \w   -128.00-102.00   0.50    0.89    -- -106.00  37.00  90.00   52
 29  \w   -127.00-101.00   0.50    0.89    -- -106.00  57.00  30.00   52
 30  \w   -130.00-105.00   0.50    0.89    -- -106.00  19.00  30.00   50
 31  \w   -175.00-149.00   0.50    0.89    -- -106.00 -37.00 120.00   52
 32  \w   -176.00-150.00   0.50    0.89    -- -106.00 -57.00  60.00   52
 33  \w   -174.00-149.00   0.50    0.89    -- -106.00 -19.00  30.00   50
 34  \w   -175.00-133.00   0.50    0.89    -- -106.00 -37.00 -30.00   84
 35  \w   -171.00-129.00   0.50    0.89    -- -106.00 -37.00-150.00   84
 36  \w   -140.00 -84.00   0.50    0.89    -- -106.00 -65.00-178.00  112
 37  \w   -157.00-131.00   0.50    0.89    -- -106.00 -37.00-180.00   52
 38  \w   -168.00-143.00   0.50    0.89    -- -106.00 -65.00-178.00   50
 39  \w   -128.00 -35.00   0.50    0.89    -- -106.00  77.00-120.00  186
;
_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      -0.0999052000
_diffrn_orient_matrix_UB_12      0.0315075000
_diffrn_orient_matrix_UB_13      0.0206742000
_diffrn_orient_matrix_UB_21      0.0405697000
_diffrn_orient_matrix_UB_22      0.0842511000
_diffrn_orient_matrix_UB_23      0.1126480000
_diffrn_orient_matrix_UB_31      -0.0034948000
_diffrn_orient_matrix_UB_32      0.0789583000
_diffrn_orient_matrix_UB_33      -0.1282444000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15931
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.162
_diffrn_reflns_theta_min         4.624
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73020
_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    1.280
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3369
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0552P)^2^+0.4439P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1039
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3056
_reflns_number_total             3369
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02517_si_003.cif
_cod_data_source_block           180409b
_cod_database_code               4036037
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C22 H15 N3'
_diffrn_oxdiff_ac3_digest_frames
;
01aca469e78e9a8779744250be38a519af02996a061
;
_diffrn_oxdiff_ac3_digest_hkl
;
0135d2198ce2769e8f4c4635428ef446cb378a
;
_reflns_odcompleteness_completeness 98.88
_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), C17(H17), C4(H4), C19(H19), C3(H3), C7(H7), C23(H23), C20(H20),
 C9(H9), C21(H21), C13(H13), C22(H22), C10(H10), C11(H11), C12(H12)
;
_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 1.514
_oxdiff_exptl_absorpt_empirical_full_min 0.568