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_7223061
_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         'C27 H18 N2, H2 O'
_chemical_formula_sum            'C27 H20 N2 O'
_chemical_formula_weight         388.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-07-13 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.297(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.6795(12)
_cell_length_b                   8.7264(8)
_cell_length_c                   26.906(2)
_cell_measurement_reflns_used    1687
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.0840
_cell_measurement_theta_min      5.3820
_cell_volume                     3840.3(5)
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega -106.00  -36.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  178.0000   90.0000 70

  2 omega -117.00  -11.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -77.0000   90.0000 106

  3 omega   72.00   98.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000   90.0000 26

  4 omega    1.00   45.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000  -60.0000 44

  5 omega   83.00  109.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 26

  6 omega   48.00   74.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 26

  7 omega  121.00  165.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000   30.0000 44

  8 omega   77.00  103.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 26

  9 omega   35.00   90.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 55

 10 omega   44.00   73.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000   30.0000 29

 11 omega   85.00  138.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 53

 12 omega  110.00  136.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   98.0000  176.0000 26

 13 omega  144.00  178.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   98.0000  176.0000 34

 14 omega   86.00  178.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -90.0000 92

 15 omega   35.00   99.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 64

 16 omega  111.00  143.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   90.0000 32

 17 omega   39.00   97.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   90.0000 58

 18 omega   29.00   55.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 26

 19 omega   42.00   79.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   90.0000 37

 20 omega   39.00   98.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 59

 21 omega   36.00   62.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 26

 22 omega   70.00   96.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 26

 23 omega   30.00   97.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 67

 24 omega   64.00   98.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -60.0000 34

 25 omega  142.00  167.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 25

 26 omega   88.00  127.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -180.0000 39

 27 omega  104.00  129.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -60.0000 25

 28 omega   73.00   98.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -115.0000  171.0000 25

 29 omega   37.00   62.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -60.0000 25

 30 omega    8.00   34.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   19.0000 -120.0000 26

 31 omega -104.00  -14.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -77.0000    0.0000 90

 32 omega  -85.00  -51.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   19.0000 -120.0000 34

 33 omega  102.00  128.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -90.0000 26

 34 omega   48.00   76.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -30.0000 28

 35 omega   63.00  109.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -180.0000 46
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0437318000
_diffrn_orient_matrix_UB_12      -0.0911189000
_diffrn_orient_matrix_UB_13      0.0359088000
_diffrn_orient_matrix_UB_21      -0.0547146000
_diffrn_orient_matrix_UB_22      0.1396263000
_diffrn_orient_matrix_UB_23      0.0043288000
_diffrn_orient_matrix_UB_31      -0.0628876000
_diffrn_orient_matrix_UB_32      -0.0582356000
_diffrn_orient_matrix_UB_33      -0.0458505000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1615
_diffrn_reflns_av_unetI/netI     0.1578
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            30214
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.996
_diffrn_reflns_theta_min         3.350
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86795
_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_density_diffrn    1.344
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         7285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1812
_refine_ls_R_factor_gt           0.0723
_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^)+(0.0446P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1604
_refine_ls_wR_factor_ref         0.2400
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2956
_reflns_number_total             7285
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra17755c2.cif
_cod_data_source_block           734
_cod_original_cell_volume        3840.4(5)
_cod_database_code               7223061
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C30 H15 N5'
_reflns_odcompleteness_completeness 94.24
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1B,H1C), O1A(H1AA,H1AB)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13),
 C14(H14), C15(H15), C16(H16), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27), C1A(H1A), C2A(H2A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A),
 C9A(H9A), C10A(H10A), C13A(H13A), C14A(H14A), C15A(H15A), C16A(H16A),
 C20A(H20A), C23A(H23A), C24A(H24A), C25A(H25A), C26A(H26A), C27A(H27A)
;
_olex2_submission_special_instructions 'No special instructions were received'