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_7223059
_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         'C22 H17 N2, C H4 O, I'
_chemical_formula_sum            'C23 H21 I N2 O'
_chemical_formula_weight         468.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-06-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-06-16 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.173(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.5184(9)
_cell_length_b                   8.2523(2)
_cell_length_c                   18.6675(5)
_cell_measurement_reflns_used    5040
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.7380
_cell_measurement_theta_min      3.1930
_cell_volume                     3923.5(2)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
  1 omega  -22.00   24.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000 -150.0000 46

  2 omega  -13.00   12.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000   60.0000 25

  3 omega   70.00   95.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152 -178.0000  -30.0000 25

  4 omega    3.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   38.0000 -150.0000 88

  5 omega    2.00   78.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152    0.0000  150.0000 76

  6 omega  -45.00   -6.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -57.0000 -180.0000 39
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0065936000
_diffrn_orient_matrix_UB_12      -0.0834292000
_diffrn_orient_matrix_UB_13      -0.0039649000
_diffrn_orient_matrix_UB_21      0.0269351000
_diffrn_orient_matrix_UB_22      -0.0205760000
_diffrn_orient_matrix_UB_23      0.0137792000
_diffrn_orient_matrix_UB_31      -0.0024624000
_diffrn_orient_matrix_UB_32      -0.0012685000
_diffrn_orient_matrix_UB_33      0.0368895000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11477
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.594
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99046
_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    1.586
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0274
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0193P)^2^+5.7602P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0565
_refine_ls_wR_factor_ref         0.0598
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3831
_reflns_number_total             4420
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra17755c2.cif
_cod_data_source_block           ole_392
_cod_database_code               7223059
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C22 H17 I N2'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C23(H23A,H23B,H23C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_shelx_res_checksum              62000
_olex2_submission_special_instructions 'No special instructions were received'