The [4+4] thermocyclization of 9-anthraldehyde: synthesis, crystal structure, experimental and theoretical UV spectra, natural bonding orbital analysis and prediction of third-order nonlinear optical properties
Zarei, Seyed Amir; Akhtari, Keivan; Piltan, Mohammad; Kamel, Shaaban M.; Mague, Joel T.; Acta Crystallographica Section C 74 (2018) –; doi:10.1107/S2053229618003534

data_2021077
_publ_section_title
;
 The [4+4] thermocyclization of 9-anthraldehyde: synthesis, crystal
 structure, experimental and theoretical UV spectra, natural bonding
 orbital analysis and prediction of third-order nonlinear optical
 properties
;
_journal_coeditor_code           YP3151
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618003534
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C30 H20 O2'
_chemical_formula_moiety         'C30 H20 O2'
_chemical_formula_sum            'C30 H20 O2'
_chemical_formula_weight         412.46
_chemical_name_systematic
Heptacyclo[8.6.6.6^2,9^.0^3,8^.0^11,16^.0^17,22^.0^23,28^]octacosa-3,5,7,11,13,15,17(22),18,20,23(28),24,26-dodecaene-1,9-carbaldehyde
_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_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 105.2170(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9627(3)
_cell_length_b                   9.6666(2)
_cell_length_c                   16.6887(4)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.4214
_cell_measurement_theta_min      3.8642
_cell_volume                     2017.86(8)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2013)
;
_computing_data_collection
;
<i>APEX2</i> (Bruker, 2013)
;
_computing_data_reduction
;
<i>SAINT</i>  (Bruker, 2013)
;
_computing_molecular_graphics
;
<i>DIAMOND</i> (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
<i>SHELXTL</i> (Sheldrick, 2008b)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            43545
_diffrn_reflns_theta_full        72.200
_diffrn_reflns_theta_max         72.458
_diffrn_reflns_theta_min         3.864
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>TWINABS</i>; Sheldrick, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.417
_refine_ls_extinction_coef       0.0024(6)
_refine_ls_extinction_expression Fc*=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2013 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0712
_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^)+(0.1517P)^2^+0.1114P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1852
_refine_ls_wR_factor_ref         0.1969
_reflns_number_gt                3312
_reflns_number_total             3965
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yp3151sup1.cif
_cod_data_source_block           I
_cod_database_code               2021077
_cod_database_fobs_code          2021077
_shelx_estimated_absorpt_t_min   0.902
_shelx_estimated_absorpt_t_max   0.981
_shelx_hkl_checksum              98097
_shelx_res_checksum              9566
_shelxl_version_number           .2013