#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/61/7056104.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_7056104
loop_
_publ_author_name
'Wu, Dong-En'
'Wang, Man-Ning'
'Luo, Yang-Hui'
'Zhang, Yawen'
'Ma, Yu-Heng'
'Sun, Baiwang'
_publ_section_title
;
 Tuning the structures and photophysical properties of
 9,10-distyrylanthrance (DSA) via fluorine substitution
;
_journal_issue                   10
_journal_name_full               'New J. Chem.'
_journal_page_first              4220
_journal_page_last               4233
_journal_paper_doi               10.1039/C6NJ03884K
_journal_volume                  41
_journal_year                    2017
_chemical_formula_sum            'C30 H20 F2'
_chemical_formula_weight         418.46
_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
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-12-10 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.92(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.3630(19)
_cell_length_b                   5.2200(10)
_cell_length_c                   21.662(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1051.0(4)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            2046
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.361
_diffrn_reflns_theta_min         1.894
_exptl_absorpt_coefficient_mu    0.088
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.009
_refine_diff_density_min         -0.003
_refine_diff_density_rms         0.001
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.455
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.455
_refine_ls_R_factor_all          0.1498
_refine_ls_R_factor_gt           0.1188
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3553
_refine_ls_wR_factor_ref         0.3852
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1272
_reflns_number_total             1921
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6nj03884k2.cif
_cod_data_source_block           X
_cod_database_code               7056104
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2014-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
F1 F 0.4428(6) 0.8834(9) 0.6770(2) 0.155(3) Uani 1 1 d . .
C1 C 0.5649(5) 1.1501(9) 0.8500(2) 0.087(3) Uani 1 1 d . .
H1A H 0.5921 1.2127 0.8899 0.105 Uiso 1 1 calc R U
C2 C 0.4573(6) 1.2684(11) 0.8126(2) 0.095(3) Uani 1 1 d . .
H2A H 0.4114 1.4093 0.8276 0.114 Uiso 1 1 calc R U
C3 C 0.4147(6) 1.1823(11) 0.7524(2) 0.095(3) Uani 1 1 d . .
H3A H 0.3417 1.2636 0.7267 0.114 Uiso 1 1 calc R U
C4 C 0.4842(6) 0.9742(11) 0.7325(2) 0.096(3) Uani 1 1 d . .
C5 C 0.5935(6) 0.8509(10) 0.7694(2) 0.090(3) Uani 1 1 d . .
H5A H 0.6389 0.7108 0.7537 0.108 Uiso 1 1 calc R U
C6 C 0.6358(5) 0.9336(9) 0.8290(2) 0.083(3) Uani 1 1 d . .
C7 C 0.7469(5) 0.7891(10) 0.8685(2) 0.088(3) Uani 1 1 d . .
H7A H 0.7982 0.6684 0.8485 0.106 Uiso 1 1 calc R U
C8 C 0.7817(5) 0.8121(9) 0.9291(2) 0.082(3) Uani 1 1 d . .
H8A H 0.7333 0.9335 0.9502 0.098 Uiso 1 1 calc R U
C9 C 0.8936(4) 0.6549(9) 0.96523(19) 0.077(3) Uani 1 1 d . .
C10 C 0.8535(5) 0.4691(9) 1.0080(2) 0.078(3) Uani 1 1 d . .
C11 C 0.7066(5) 0.4354(10) 1.0175(2) 0.084(3) Uani 1 1 d . .
H11A H 0.6365 0.5408 0.9968 0.100 Uiso 1 1 calc R U
C12 C 0.6683(5) 0.2524(12) 1.0563(2) 0.094(3) Uani 1 1 d . .
H12A H 0.5721 0.2340 1.0623 0.113 Uiso 1 1 calc R U
C13 C 0.7725(5) 0.0887(10) 1.0878(2) 0.090(3) Uani 1 1 d . .
H13A H 0.7442 -0.0400 1.1134 0.108 Uiso 1 1 calc R U
C14 C 0.9117(5) 0.1172(9) 1.0812(2) 0.084(3) Uani 1 1 d . .
H14A H 0.9791 0.0093 1.1029 0.101 Uiso 1 1 calc R U
C15 C 0.9590(5) 0.3111(8) 1.04137(19) 0.076(3) Uani 1 1 d . .
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'
F F 0.0171 0.0103 '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
C2 C1 C6 120.9(5) .
C2 C1 H1A 119.5 .
C6 C1 H1A 119.5 .
C1 C2 C3 121.2(5) .
C1 C2 H2A 119.4 .
C3 C2 H2A 119.4 .
C4 C3 C2 117.4(5) .
C4 C3 H3A 121.3 .
C2 C3 H3A 121.3 .
F1 C4 C3 118.7(5) .
F1 C4 C5 118.7(5) .
C3 C4 C5 122.6(5) .
C6 C5 C4 120.5(5) .
C6 C5 H5A 119.8 .
C4 C5 H5A 119.8 .
C5 C6 C1 117.4(4) .
C5 C6 C7 119.2(5) .
C1 C6 C7 123.3(4) .
C8 C7 C6 127.1(5) .
C8 C7 H7A 116.4 .
C6 C7 H7A 116.4 .
C7 C8 C9 123.4(4) .
C7 C8 H8A 118.3 .
C9 C8 H8A 118.3 .
C15 C9 C10 119.2(4) 3_767
C15 C9 C8 120.9(4) 3_767
C10 C9 C8 119.9(4) .
C15 C10 C9 120.5(4) .
C15 C10 C11 118.7(4) .
C9 C10 C11 120.9(4) .
C12 C11 C10 120.8(4) .
C12 C11 H11A 119.6 .
C10 C11 H11A 119.6 .
C11 C12 C13 120.7(4) .
C11 C12 H12A 119.7 .
C13 C12 H12A 119.7 .
C14 C13 C12 120.5(5) .
C14 C13 H13A 119.8 .
C12 C13 H13A 119.8 .
C13 C14 C15 121.3(4) .
C13 C14 H14A 119.4 .
C15 C14 H14A 119.4 .
C9 C15 C10 120.2(4) 3_767
C9 C15 C14 121.7(4) 3_767
C10 C15 C14 118.1(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C4 1.306(6) .
C1 C2 1.362(7) .
C1 C6 1.413(7) .
C1 H1A 0.9300 .
C2 C3 1.392(7) .
C2 H2A 0.9300 .
C3 C4 1.362(8) .
C3 H3A 0.9300 .
C4 C5 1.379(7) .
C5 C6 1.375(7) .
C5 H5A 0.9300 .
C6 C7 1.473(6) .
C7 C8 1.319(6) .
C7 H7A 0.9300 .
C8 C9 1.479(6) .
C8 H8A 0.9300 .
C9 C15 1.415(6) 3_767
C9 C10 1.422(6) .
C10 C15 1.417(6) .
C10 C11 1.426(6) .
C11 C12 1.349(7) .
C11 H11A 0.9300 .
C12 C13 1.411(7) .
C12 H12A 0.9300 .
C13 C14 1.336(7) .
C13 H13A 0.9300 .
C14 C15 1.435(6) .
C14 H14A 0.9300 .
C15 C9 1.415(6) 3_767
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -0.8(8) . .
C1 C2 C3 C4 0.4(8) . .
C2 C3 C4 F1 177.4(5) . .
C2 C3 C4 C5 -0.5(8) . .
F1 C4 C5 C6 -177.1(5) . .
C3 C4 C5 C6 0.8(8) . .
C4 C5 C6 C1 -1.1(7) . .
C4 C5 C6 C7 176.5(5) . .
C2 C1 C6 C5 1.1(7) . .
C2 C1 C6 C7 -176.4(5) . .
C5 C6 C7 C8 -167.0(5) . .
C1 C6 C7 C8 10.5(8) . .
C6 C7 C8 C9 178.9(4) . .
C7 C8 C9 C15 70.0(6) . 3_767
C7 C8 C9 C10 -110.9(6) . .
C15 C9 C10 C15 -3.1(7) 3_767 .
C8 C9 C10 C15 177.9(4) . .
C15 C9 C10 C11 177.8(4) 3_767 .
C8 C9 C10 C11 -1.3(7) . .
C15 C10 C11 C12 -1.7(7) . .
C9 C10 C11 C12 177.4(5) . .
C10 C11 C12 C13 -0.6(8) . .
C11 C12 C13 C14 2.0(8) . .
C12 C13 C14 C15 -1.0(8) . .
C9 C10 C15 C9 3.1(7) . 3_767
C11 C10 C15 C9 -177.7(4) . 3_767
C9 C10 C15 C14 -176.5(4) . .
C11 C10 C15 C14 2.6(6) . .
C13 C14 C15 C9 179.1(4) . 3_767
C13 C14 C15 C10 -1.3(7) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139177788
