A new heterocyclic skeleton with highly tunable absorbtion/emission wavelength via H-bonding
Tomashenko, Olesya A.; Khlebnikov, Alexander F.; Mosiagin, Ivan P.; Novikov, Mikhail S.; Grachova, Elena Valeri; Shakirova, Julia R.; Tunik, Sergey P.; RSC Adv.  (2015) –; doi:10.1039/C5RA17755C

data_7223060
_publ_section_title
;
 A new heterocyclic skeleton with highly tunable absorbtion/emission
 wavelength via H-bonding
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA17755C
_journal_year                    2015
_chemical_formula_moiety         'C21 H14 N2, 0.5(H2 O)'
_chemical_formula_sum            'C21 H15 N2 O0.5'
_chemical_formula_weight         303.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-12-30
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2015-06-17 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.754(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.5157(6)
_cell_length_b                   8.5175(2)
_cell_length_c                   19.8322(5)
_cell_measurement_reflns_used    8150
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.9590
_cell_measurement_theta_min      4.4910
_cell_volume                     2943.86(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9843
_diffrn_measured_fraction_theta_max 0.9843
_diffrn_measurement_details
;
  1 omega -110.00  -15.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000  150.0000 95

  2 omega  -50.00   21.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -60.0000 71

  3 omega    1.00   35.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000   60.0000 34

  4 omega   39.00   66.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000   30.0000 27

  5 omega   63.00   94.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000   90.0000 31

  6 omega  145.00  176.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  120.0000 31

  7 omega  104.00  131.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  120.0000 27

  8 omega   57.00   86.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -120.0000 29

  9 omega   54.00   90.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -120.0000 36

 10 omega  119.00  144.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  120.0000 25

 11 omega  109.00  142.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -120.0000 33

 12 omega  152.00  178.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -120.0000 26

 13 omega   40.00   76.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -180.0000 36

 14 omega   30.00   59.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 29

 15 omega   48.00   90.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 42

 16 omega   41.00   75.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 34

 17 omega   39.00   95.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 56

 18 omega   58.00  146.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 88

 19 omega   73.00  109.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 36

 20 omega  100.00  127.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 27

 21 omega  143.00  168.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 25

 22 omega   45.00   70.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -150.0000 25

 23 omega  102.00  143.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -150.0000 41

 24 omega   52.00   77.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 25

 25 omega  100.00  142.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  150.0000 42

 26 omega   94.00  144.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -120.0000 50

 27 omega  112.00  138.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 26

 28 omega  -35.00    6.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -19.0000  -60.0000 41

 29 omega  -93.00  -48.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -19.0000  -60.0000 45

 30 omega   66.00  116.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   38.0000  120.0000 50

 31 omega   28.00   56.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   38.0000  120.0000 28

 32 omega   11.00   49.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   57.0000  -30.0000 38

 33 omega   57.00  123.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  120.0000 66

 34 omega   58.00  128.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -90.0000 70

 35 omega   83.00  146.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 63

 36 omega   83.00  115.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 32

 37 omega   65.00  114.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  120.0000 49

 38 omega   90.00  165.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 75

 39 omega  103.00  146.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -30.0000 43

 40 omega   68.00  115.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 47

 41 omega   41.00   84.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 43

 42 omega   85.00  117.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 32

 43 omega  149.00  176.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   60.0000 27

 44 omega   34.00   79.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   30.0000 45

 45 omega  101.00  127.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 26

 46 omega  151.00  176.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000    0.0000 25

 47 omega   62.00  108.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 46

 48 omega   58.00  100.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -90.0000 42

 49 omega   58.00   87.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   30.0000 29

 50 omega   47.00   73.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 26

 51 omega   31.00   58.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 27

 52 omega   85.00  111.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 26

 53 omega  130.00  156.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 26

 54 omega  148.00  174.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 26

 55 omega   77.00  106.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000 -150.0000 29

 56 omega   55.00  100.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 45

 57 omega   65.00   92.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 27

 58 omega   40.00   66.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000 -150.0000 26

 59 omega   96.00  121.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 25

 60 omega  135.00  166.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000 -150.0000 31

 61 omega  116.00  143.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   90.0000 27

 62 omega   43.00   69.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 26

 63 omega   44.00   69.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 25

 64 omega   61.00   87.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 26

 65 omega   96.00  133.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   60.0000 37

 66 omega   85.00  143.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 58

 67 omega  144.00  169.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   12.0000  -78.0145 25

 68 omega  104.00  144.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   60.0000 40

 69 omega   95.00  141.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -180.0000 46

 70 omega  121.00  147.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 26

 71 omega  137.00  178.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000    0.0000 41

 72 omega   92.00  118.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -120.0000 26

 73 omega   30.00   56.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000 -180.0000 26

 74 omega   45.00   71.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   12.0000  -78.0145 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0854452000
_diffrn_orient_matrix_UB_12      -0.0378845000
_diffrn_orient_matrix_UB_13      0.0039609000
_diffrn_orient_matrix_UB_21      0.0054853000
_diffrn_orient_matrix_UB_22      -0.1358826000
_diffrn_orient_matrix_UB_23      -0.0505978000
_diffrn_orient_matrix_UB_31      0.0220268000
_diffrn_orient_matrix_UB_32      -0.1131518000
_diffrn_orient_matrix_UB_33      0.0593306000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            45149
_diffrn_reflns_theta_full        72.49
_diffrn_reflns_theta_max         72.49
_diffrn_reflns_theta_min         3.21
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     440
_refine_ls_number_reflns         5846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0617P)^2^+0.9001P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1499
_reflns_number_gt                3646
_reflns_number_total             5846
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra17755c2.cif
_cod_data_source_block           ole468
_cod_original_cell_volume        2943.85(15)
_cod_original_formula_sum        'C21 H15 N2 O0.50'
_cod_database_code               7223060
_chemical_oxdiff_formula         'C21 N2 h18'
_reflns_odcompleteness_completeness 94.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95