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_4032827
_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 H28 N2 S2'
_chemical_formula_sum            'C24 H28 N2 S2'
_chemical_formula_weight         408.60
_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             2017-02-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.1030(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7063(4)
_cell_length_b                   10.0708(3)
_cell_length_c                   14.2801(4)
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      66.72
_cell_measurement_theta_min      4.391
_cell_volume                     2075.36(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      110.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23120
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.731
_diffrn_reflns_theta_max         66.731
_diffrn_reflns_theta_min         3.062
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.402
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) was 0.0829 before and 0.0481 after correction. The Ratio of minimum to maximum transmission is 0.7823. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.069
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.00093(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0384P)^2^+1.6269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0888
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3374
_reflns_number_total             3655
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01647_si_002.cif
_cod_data_source_block           aja01
_cod_depositor_comments
'Adding full bibliography for 4032827--4032828.cif.'
_cod_database_code               4032827
_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:
 C00G(H00G), C00I(H00I)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00B,H00C), C00M(H00H,H00K), C00N(H00L,H00M), C00P(H00Q,H00R)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A), C00D(H00D), C00E(H00E), C00F(H00F), C00J(H00J)
2.d Idealised Me refined as rotating group:
 C00O(H00N,H00O,H00P), C00Q(H00S,H00T,H00U), C00R(H00V,H00W,H00X), C00S(H00Y,H,
 HA)
;
_olex2_submission_special_instructions 'No special instructions were received'