Intense Absorption of Azulene Realized by Molecular Orbital Inversion
Tsuchiya, Takahiro; Hamano, Tomohiro; Inoue, Masahiro; Nakamura, Tomoya; Wakamiya, Atsushi; Mazaki, Yasuhiro; Chemical Communications  (2023) –; doi:10.1039/D3CC02311G

data_7131932
_publ_section_title
;
 Intense Absorption of Azulene Realized by Molecular Orbital Inversion
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC02311G
_journal_year                    2023
_chemical_formula_moiety         '2(C17 H13 N)'
_chemical_formula_sum            'C34 H26 N2'
_chemical_formula_weight         462.57
_chemical_melting_point          511.0(10)
_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'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2022-07-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-05-02 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.106(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0145(2)
_cell_length_b                   10.9285(2)
_cell_length_c                   12.2912(2)
_cell_measurement_reflns_used    5118
_cell_measurement_temperature    120
_cell_measurement_theta_max      74.2810
_cell_measurement_theta_min      5.4350
_cell_volume                     1207.76(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11892
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.878
_diffrn_reflns_theta_min         5.422
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              PhotonJet-S
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88008
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'dark brown'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform/hexane'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0040(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2501
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0322P)^2^+0.4291P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0913
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2366
_reflns_number_total             2501
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02311g2.cif
_cod_data_source_block           2a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '510-512' was changed to
'511.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               7131932
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.915
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C7 \\sim C8 \\sim C9 \\sim C10:
within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9)
\\sim Ueq, Uanis(C10) \\sim Ueq: with sigma of 0.05 and sigma for terminal
atoms of 0.1
3. Others
 Fixed Sof: C1(0.5) C2(0.5) H2(0.5) C3(0.5) C4(0.5) H4(0.5) C5(0.5) H5(0.5)
 C6(0.5) C7(0.5) H7(0.5) C8(0.5) H8(0.5) C9(0.5) C10(0.5) H10(0.5)
;
_shelx_res_checksum              78994
_shelx_hkl_checksum              60598
_olex2_submission_special_instructions 'No special instructions were received'