Synthesis and properties of fluorescent 4'-azulenyl-functionalized 2,2':6',2″-terpyridines.
Ion, Adrian E.; Cristian, Liliana; Voicescu, Mariana; Bangesh, Masroor; Madalan, Augustin M.; Bala, Daniela; Mihailciuc, Constantin; Nica, Simona; Beilstein journal of organic chemistry 12 (2016) 1812–1825; doi:10.3762/bjoc.12.171

data_4032042
_publ_section_title
;
 Synthesis and properties of fluorescent 4'-azulenyl-functionalized
 2,2':6',2&#x2033;-terpyridines.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              1812
_journal_page_last               1825
_journal_paper_doi               10.3762/bjoc.12.171
_journal_volume                  12
_journal_year                    2016
_chemical_formula_sum            'C25 H17 N3'
_chemical_formula_weight         359.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P -2n 2a'
_space_group_name_H-M_alt        'P 21 c n'
_symmetry_space_group_name_Hall  'P -2n 2a'
_symmetry_space_group_name_H-M   'P 21 c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0110(4)
_cell_length_b                   9.5419(6)
_cell_length_c                   31.230(3)
_cell_measurement_reflns_used    10533
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      30.99
_cell_measurement_theta_min      2.23
_cell_volume                     1791.2(2)
_computing_cell_refinement       X-Area
_computing_data_collection       X-Area
_computing_data_reduction        X-Area
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            17996
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         2.232
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.8933
_exptl_absorpt_correction_T_min  0.8577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 784 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.8(10)
_refine_ls_extinction_coef       0.024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3827
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0610P)^2^+0.2971P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1398
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                2424
_reflns_number_total             3827
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-12-171-S2.cif
_cod_data_source_block           Compound_4a
_cod_depositor_comments          'Adding full bibliography for 4032042.cif.'
_cod_database_code               4032042
_shelxl_version_number           2014-3
_shelx_res_checksum              74335
_shelx_hkl_checksum              77611