#------------------------------------------------------------------------------
#$Date: 2025-04-05 05:20:34 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298792 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/38/1573801.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1573801
loop_
_publ_author_name
'Martinez-Fernandez, L'
'Wu, Peicong'
'Bao, Lin-Tao'
'Wang, Xueli'
'Zhang, Rui-Hua'
'Wang, Wei'
'Yang, Hai-Bo'
'Chen, Jinquan'
'Improta, R.'
_publ_section_title
;
 On the nature of the triplet electronic states of naphthalene dimers.
;
_journal_issue                   10
_journal_name_full               'Chemical science'
_journal_page_first              4469
_journal_page_last               4479
_journal_paper_doi               10.1039/d4sc07982e
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C24 H20'
_chemical_formula_sum            'C24 H20'
_chemical_formula_weight         308.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-11-25 deposited with the CCDC.	2025-01-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4210(17)
_cell_length_b                   13.116(3)
_cell_length_c                   15.113(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1669.2(6)
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6049
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.056
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 1291 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   6.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0573
_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/[σ²(Fo²)+(0.0890P)²+0.1783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1544
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                3128
_reflns_number_total             3281
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc07982e2.cif
_cod_data_source_block           work
_cod_depositor_comments
'Adding full bibliography for 1573801--1573804.cif.'
_cod_database_code               1573801
_shelxl_version_number           2013-4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C23(H23A,H23B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15),
 C17(H17), C20(H20), C21(H21), C22(H22)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.4139(2) -0.52344(16) -0.72337(15) 0.0361(5) Uani 1 1 d . . . . .
C2 C -0.0706(3) -0.64782(18) -0.75663(14) 0.0399(5) Uani 1 1 d . . . . .
C3 C -0.3427(3) -0.49468(16) -0.80570(15) 0.0368(5) Uani 1 1 d . . . . .
C4 C -0.1969(3) -0.71785(17) -0.74157(16) 0.0422(5) Uani 1 1 d . . . . .
C5 C -0.3652(3) -0.47179(19) -0.64564(15) 0.0466(6) Uani 1 1 d . . . . .
H5 H -0.4137 -0.4872 -0.5920 0.056 Uiso 1 1 calc R . . . .
C6 C 0.0095(3) -0.6058(2) -0.68240(18) 0.0491(6) Uani 1 1 d . . . . .
H6 H 0.0941 -0.5613 -0.6910 0.059 Uiso 1 1 calc R . . . .
C7 C -0.2025(3) -0.43202(17) -0.80345(17) 0.0461(6) Uani 1 1 d . . . . .
C8 C -0.5263(3) -0.6052(2) -0.72234(18) 0.0474(6) Uani 1 1 d . . . . .
C9 C -0.2487(4) -0.40010(19) -0.64813(18) 0.0554(7) Uani 1 1 d . . . . .
H9 H -0.2260 -0.3619 -0.5979 0.067 Uiso 1 1 calc R . . . .
C10 C -0.1636(3) -0.38383(18) -0.7256(2) 0.0563(7) Uani 1 1 d . . . . .
H10 H -0.0779 -0.3391 -0.7248 0.068 Uiso 1 1 calc R . . . .
C11 C -0.2617(3) -0.72630(19) -0.65380(17) 0.0506(6) Uani 1 1 d . . . . .
C12 C -0.1762(4) -0.6869(2) -0.58472(16) 0.0569(7) Uani 1 1 d . . . . .
H12 H -0.2112 -0.6978 -0.5272 0.068 Uiso 1 1 calc R . . . .
C13 C -0.2559(4) -0.7742(2) -0.8154(2) 0.0610(7) Uani 1 1 d . . . . .
H13 H -0.3373 -0.8212 -0.8074 0.073 Uiso 1 1 calc R . . . .
C14 C -0.0366(4) -0.6302(2) -0.59868(17) 0.0559(7) Uani 1 1 d . . . . .
H14 H 0.0243 -0.6093 -0.5506 0.067 Uiso 1 1 calc R . . . .
C15 C -0.4104(3) -0.5321(2) -0.88505(17) 0.0528(7) Uani 1 1 d . . . . .
H15 H -0.3683 -0.5124 -0.9393 0.063 Uiso 1 1 calc R . . . .
C16 C -0.0305(3) -0.6200(2) -0.84628(16) 0.0519(7) Uani 1 1 d . . . . .
C17 C -0.5909(3) -0.6367(2) -0.8012(2) 0.0646(8) Uani 1 1 d . . . . .
H17 H -0.6714 -0.6852 -0.8009 0.078 Uiso 1 1 calc R . . . .
C18 C -0.0847(4) -0.4328(2) -0.8789(2) 0.0646(8) Uani 1 1 d . . . . .
H18A H -0.0339 -0.3666 -0.8830 0.078 Uiso 1 1 calc R . . . .
H18B H -0.1405 -0.4451 -0.9341 0.078 Uiso 1 1 calc R . . . .
C19 C -0.5495(4) -0.6702(2) -0.6401(2) 0.0644(8) Uani 1 1 d . . . . .
H19A H -0.6577 -0.6955 -0.6384 0.077 Uiso 1 1 calc R . . . .
H19B H -0.5321 -0.6289 -0.5877 0.077 Uiso 1 1 calc R . . . .
C20 C -0.1936(5) -0.7593(3) -0.8975(2) 0.0729(10) Uani 1 1 d . . . . .
H20 H -0.2227 -0.8024 -0.9436 0.088 Uiso 1 1 calc R . . . .
C21 C -0.5375(4) -0.5970(3) -0.8822(2) 0.0663(9) Uani 1 1 d . . . . .
H21 H -0.5891 -0.6149 -0.9343 0.080 Uiso 1 1 calc R . . . .
C22 C -0.0863(4) -0.6799(3) -0.91347(18) 0.0680(9) Uani 1 1 d . . . . .
H22 H -0.0522 -0.6676 -0.9710 0.082 Uiso 1 1 calc R . . . .
C23 C -0.4321(4) -0.7615(2) -0.6400(3) 0.0707(9) Uani 1 1 d . . . . .
H23A H -0.4400 -0.7973 -0.5841 0.085 Uiso 1 1 calc R . . . .
H23B H -0.4611 -0.8086 -0.6868 0.085 Uiso 1 1 calc R . . . .
C24 C 0.0448(4) -0.5167(3) -0.8658(2) 0.0688(9) Uani 1 1 d . . . . .
H24A H 0.1092 -0.5217 -0.9189 0.083 Uiso 1 1 calc R . . . .
H24B H 0.1138 -0.4976 -0.8171 0.083 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C1 C3 118.2(2) . . ?
C5 C1 C8 122.8(2) . . ?
C8 C1 C3 119.0(2) . . ?
C4 C2 C16 119.2(2) . . ?
C6 C2 C4 118.6(2) . . ?
C6 C2 C16 122.2(2) . . ?
C1 C3 C7 118.3(2) . . ?
C15 C3 C1 118.4(2) . . ?
C15 C3 C7 123.3(2) . . ?
C2 C4 C11 118.7(2) . . ?
C2 C4 C13 118.0(2) . . ?
C13 C4 C11 123.3(3) . . ?
C9 C5 C1 121.1(2) . . ?
C14 C6 C2 120.5(3) . . ?
C3 C7 C18 121.1(3) . . ?
C10 C7 C3 118.6(2) . . ?
C10 C7 C18 119.5(3) . . ?
C1 C8 C19 121.0(2) . . ?
C17 C8 C1 118.5(3) . . ?
C17 C8 C19 119.4(3) . . ?
C5 C9 C10 120.1(2) . . ?
C7 C10 C9 121.8(2) . . ?
C4 C11 C23 120.5(3) . . ?
C12 C11 C4 118.3(2) . . ?
C12 C11 C23 120.4(3) . . ?
C11 C12 C14 121.7(2) . . ?
C20 C13 C4 120.3(3) . . ?
C6 C14 C12 120.1(3) . . ?
C21 C15 C3 120.2(3) . . ?
C2 C16 C24 120.2(3) . . ?
C22 C16 C2 118.1(3) . . ?
C22 C16 C24 120.7(3) . . ?
C8 C17 C21 121.2(3) . . ?
C7 C18 C24 111.5(2) . . ?
C8 C19 C23 110.6(2) . . ?
C13 C20 C22 120.8(3) . . ?
C15 C21 C17 120.6(2) . . ?
C16 C22 C20 121.4(3) . . ?
C11 C23 C19 111.5(2) . . ?
C16 C24 C18 111.1(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.432(3) . ?
C1 C5 1.417(3) . ?
C1 C8 1.430(3) . ?
C2 C4 1.424(3) . ?
C2 C6 1.420(4) . ?
C2 C16 1.443(3) . ?
C3 C7 1.438(3) . ?
C3 C15 1.416(3) . ?
C4 C11 1.439(3) . ?
C4 C13 1.427(4) . ?
C5 C9 1.359(4) . ?
C6 C14 1.362(4) . ?
C7 C10 1.375(4) . ?
C7 C18 1.512(4) . ?
C8 C17 1.373(4) . ?
C8 C19 1.520(4) . ?
C9 C10 1.390(4) . ?
C11 C12 1.370(4) . ?
C11 C23 1.521(4) . ?
C12 C14 1.406(5) . ?
C13 C20 1.362(5) . ?
C15 C21 1.369(5) . ?
C16 C22 1.367(4) . ?
C16 C24 1.525(5) . ?
C17 C21 1.404(5) . ?
C18 C24 1.562(4) . ?
C19 C23 1.552(4) . ?
C20 C22 1.400(5) . ?
