A Naphtho-p-quinodimethane Exhibiting Baird's (Anti)Aromaticity, Broken Symmetry, and Attractive Photoluminescence.
Shokri, Siamak; Li, Jingbai; Manna, Manoj K.; Wiederrecht, Gary P.; Gosztola, David J.; Ugrinov, Angel; Jockusch, Steffen; Rogachev, Andrey Yu; Ayitou, A Jean-Luc; The Journal of organic chemistry 82 (2017) 10167–10173; doi:10.1021/acs.joc.7b01647

data_4032828
_publ_section_title
;
 A Naphtho-p-quinodimethane Exhibiting Baird's (Anti)Aromaticity, Broken
 Symmetry, and Attractive Photoluminescence.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10167
_journal_page_last               10173
_journal_paper_doi               10.1021/acs.joc.7b01647
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C24 H26 N2 O4'
_chemical_formula_sum            'C24 H26 N2 O4'
_chemical_formula_weight         406.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.47(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.136(7)
_cell_length_b                   8.483(7)
_cell_length_c                   13.462(9)
_cell_measurement_reflns_used    1294
_cell_measurement_temperature    199(2)
_cell_measurement_theta_max      24.444
_cell_measurement_theta_min      2.264
_cell_volume                     1025.9(13)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      199.0
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0896
_diffrn_reflns_av_unetI/netI     0.1242
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5806
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.198
_diffrn_reflns_theta_max         25.198
_diffrn_reflns_theta_min         2.852
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.2512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1833 before and 0.0994 after correction. The Ratio of minimum to maximum transmission is 0.3371. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0716
_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^)+(0.0637P)^2^+0.0875P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1739
_refine_ls_wR_factor_ref         0.2009
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1075
_reflns_number_total             1808
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01647_si_001.cif
_cod_data_source_block           scan_0m
_cod_depositor_comments
'Adding full bibliography for 4032827--4032828.cif.'
_cod_original_cell_volume        1026.0(13)
_cod_database_code               4032828
_shelx_shelxl_version_number     2016/4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00C(H00C,H00D), C00D(H00E,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A)
2.d Idealised Me refined as rotating group:
 C00E(H00G,H00H,H00I), C00F(H00J,H00K,H00L)
;
_olex2_submission_special_instructions 'No special instructions were received'