#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:39:38 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229156 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/01/7230145.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_7230145
loop_
_publ_author_name
'Song, Xiaoxian'
'Yu, Hanbo'
'Zhang, Yuewei'
'Miao, Yang'
'Ye, Kaiqi'
'Wang, Yue'
_publ_section_title
;
 Controllable morphology and self-assembly of one-dimensional luminescent
 crystals based on alkyl-fluoro-substituted dithienophenazines
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              1669
_journal_paper_doi               10.1039/C8CE00021B
_journal_volume                  20
_journal_year                    2018
_chemical_formula_sum            'C24 H22 F2 N2 S2'
_chemical_formula_weight         440.56
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-10-12 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.408(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9401(5)
_cell_length_b                   27.416(3)
_cell_length_c                   15.4519(14)
_cell_measurement_reflns_used    2291
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2181
_cell_measurement_theta_min      2.5924
_cell_volume                     2083.5(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13026
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.287
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4084
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0590P)²+0.0579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1251
_reflns_number_gt                3236
_reflns_number_total             4084
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ce00021b2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7230145--7230148.cif.'
_cod_original_cell_volume        2083.5(3)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7230145
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.31768(12) 0.41875(2) 0.35812(4) 0.02589(19) Uani 1 1 d .
S2 S 0.77015(12) 0.51520(2) 0.41253(4) 0.02520(19) Uani 1 1 d .
F1 F -0.4479(3) 0.61914(6) -0.12244(9) 0.0365(4) Uani 1 1 d .
N2 N -0.0563(4) 0.52268(8) 0.11198(13) 0.0243(5) Uani 1 1 d .
F3 F -0.0753(3) 0.68727(6) -0.08966(10) 0.0404(4) Uani 1 1 d .
C4 C 0.1384(5) 0.60169(9) 0.08335(15) 0.0228(6) Uani 1 1 d .
N5 N 0.3294(4) 0.59857(8) 0.15138(12) 0.0233(5) Uani 1 1 d .
C6 C 0.3291(4) 0.55823(9) 0.19941(15) 0.0215(5) Uani 1 1 d .
C7 C 0.1343(5) 0.51955(9) 0.17920(15) 0.0206(5) Uani 1 1 d .
C8 C 0.5261(4) 0.51187(9) 0.32497(15) 0.0226(6) Uani 1 1 d .
C9 C 0.5250(4) 0.55324(9) 0.27396(15) 0.0220(5) Uani 1 1 d .
C10 C -0.0576(5) 0.56387(9) 0.06361(15) 0.0225(6) Uani 1 1 d .
C11 C 0.3391(5) 0.47316(9) 0.30384(15) 0.0220(6) Uani 1 1 d .
C12 C -0.0612(5) 0.64784(10) -0.03717(16) 0.0274(6) Uani 1 1 d .
C13 C 0.1458(4) 0.47628(9) 0.23356(15) 0.0221(6) Uani 1 1 d .
C14 C -0.2583(5) 0.61112(10) -0.05522(16) 0.0274(6) Uani 1 1 d .
C15 C 1.1686(5) 0.64863(10) 0.40082(16) 0.0272(6) Uani 1 1 d .
H15A H 1.0060 0.6687 0.3964 0.033 Uiso 1 1 calc R
H15B H 1.2281 0.6454 0.3430 0.033 Uiso 1 1 calc R
C16 C -0.0743(5) 0.34976(10) 0.29580(17) 0.0298(6) Uani 1 1 d .
H16A H -0.1978 0.3427 0.2448 0.036 Uiso 1 1 calc R
H16B H -0.1804 0.3504 0.3455 0.036 Uiso 1 1 calc R
C17 C 1.1012(5) 0.59853(9) 0.43450(16) 0.0251(6) Uani 1 1 d .
H17A H 1.2635 0.5785 0.4371 0.030 Uiso 1 1 calc R
H17B H 1.0500 0.6019 0.4933 0.030 Uiso 1 1 calc R
C18 C 0.0470(5) 0.39953(10) 0.28528(16) 0.0255(6) Uani 1 1 d .
C19 C 0.8755(5) 0.57262(9) 0.38030(16) 0.0232(6) Uani 1 1 d .
C20 C 0.7284(5) 0.58760(9) 0.30638(15) 0.0231(6) Uani 1 1 d .
H20A H 0.7568 0.6173 0.2795 0.028 Uiso 1 1 calc R
C21 C -0.2583(5) 0.57004(10) -0.00725(16) 0.0277(6) Uani 1 1 d .
H21A H -0.3885 0.5460 -0.0206 0.033 Uiso 1 1 calc R
C22 C 0.1327(5) 0.64378(10) 0.02988(16) 0.0269(6) Uani 1 1 d .
H22A H 0.2613 0.6683 0.0410 0.032 Uiso 1 1 calc R
C23 C 1.3904(5) 0.67375(10) 0.45996(18) 0.0331(7) Uani 1 1 d .
H23A H 1.3293 0.6769 0.5176 0.040 Uiso 1 1 calc R
H23B H 1.5512 0.6533 0.4648 0.040 Uiso 1 1 calc R
C24 C 0.1324(5) 0.30874(9) 0.30832(17) 0.0299(6) Uani 1 1 d .
H24A H 0.2465 0.3092 0.2606 0.036 Uiso 1 1 calc R
H24B H 0.2483 0.3145 0.3616 0.036 Uiso 1 1 calc R
C25 C -0.0212(5) 0.43400(9) 0.22423(15) 0.0250(6) Uani 1 1 d .
H25A H -0.1629 0.4304 0.1806 0.030 Uiso 1 1 calc R
C26 C 0.0032(6) 0.25871(11) 0.3128(2) 0.0418(8) Uani 1 1 d .
H26A H -0.1078 0.2580 0.3613 0.050 Uiso 1 1 calc R
H26B H -0.1159 0.2533 0.2601 0.050 Uiso 1 1 calc R
C27 C 1.4670(6) 0.72382(11) 0.4287(2) 0.0486(8) Uani 1 1 d .
H27A H 1.6061 0.7375 0.4690 0.073 Uiso 1 1 calc R
H27B H 1.3099 0.7446 0.4247 0.073 Uiso 1 1 calc R
H27C H 1.5334 0.7210 0.3725 0.073 Uiso 1 1 calc R
C28 C 0.2075(7) 0.21768(12) 0.3233(2) 0.0572(10) Uani 1 1 d .
H28A H 0.1136 0.1872 0.3264 0.086 Uiso 1 1 calc R
H28B H 0.3249 0.2225 0.3757 0.086 Uiso 1 1 calc R
H28C H 0.3140 0.2173 0.2744 0.086 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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 '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
C11 S1 C18 91.49(12)
C8 S2 C19 91.66(12)
C7 N2 C10 116.7(2)
N5 C4 C22 118.7(2)
N5 C4 C10 122.0(2)
C22 C4 C10 119.3(2)
C6 N5 C4 116.8(2)
N5 C6 C9 119.3(2)
N5 C6 C7 121.6(2)
C9 C6 C7 119.1(2)
N2 C7 C6 121.7(2)
N2 C7 C13 119.2(2)
C6 C7 C13 119.0(2)
C9 C8 C11 120.9(2)
C9 C8 S2 111.64(18)
C11 C8 S2 127.5(2)
C8 C9 C20 112.0(2)
C8 C9 C6 120.1(2)
C20 C9 C6 127.9(2)
N2 C10 C21 119.5(2)
N2 C10 C4 121.2(2)
C21 C10 C4 119.2(2)
C13 C11 C8 121.3(2)
C13 C11 S1 111.58(18)
C8 C11 S1 127.07(18)
C22 C12 F3 121.4(2)
C22 C12 C14 121.4(2)
F3 C12 C14 117.2(2)
C11 C13 C25 112.4(2)
C11 C13 C7 119.5(2)
C25 C13 C7 128.1(2)
C21 C14 F1 121.6(2)
C21 C14 C12 121.5(2)
F1 C14 C12 116.9(2)
C17 C15 C23 111.9(2)
C18 C16 C24 114.5(2)
C19 C17 C15 114.3(2)
C25 C18 C16 129.2(2)
C25 C18 S1 111.31(19)
C16 C18 S1 119.51(18)
C20 C19 C17 129.3(2)
C20 C19 S2 111.24(18)
C17 C19 S2 119.43(18)
C19 C20 C9 113.4(2)
C14 C21 C10 119.3(2)
C12 C22 C4 119.3(2)
C27 C23 C15 113.9(2)
C26 C24 C16 113.2(2)
C18 C25 C13 113.2(2)
C28 C26 C24 113.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C11 1.720(3)
S1 C18 1.746(2)
S2 C8 1.728(2)
S2 C19 1.745(3)
F1 C14 1.349(3)
N2 C7 1.337(3)
N2 C10 1.354(3)
F3 C12 1.349(3)
C4 N5 1.347(3)
C4 C22 1.418(3)
C4 C10 1.432(3)
N5 C6 1.332(3)
C6 C9 1.439(3)
C6 C7 1.446(3)
C7 C13 1.452(3)
C8 C9 1.381(3)
C8 C11 1.425(3)
C9 C20 1.433(3)
C10 C21 1.416(3)
C11 C13 1.379(3)
C12 C22 1.348(3)
C12 C14 1.410(4)
C13 C25 1.422(3)
C14 C21 1.348(4)
C15 C17 1.517(3)
C15 C23 1.524(3)
C16 C18 1.505(3)
C16 C24 1.519(4)
C17 C19 1.508(3)
C18 C25 1.355(3)
C19 C20 1.358(3)
C23 C27 1.515(4)
C24 C26 1.517(4)
C26 C28 1.510(4)
