#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/38/7123829.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_7123829
loop_
_publ_author_name
'Zhang, Zhenglin'
'Lieu, Thien'
'Wu, Chia-Hua'
'Wang, Xiqu'
'Wu, Judy I-Chia'
'Daugulis, Olafs'
'Miljanic, Ognjen Š.'
_publ_section_title
;
 Solvation-Dependent Switching of Solid-state Luminescence of a
 Fluorinated Aromatic Tetrapyrazole
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03932E
_journal_year                    2019
_chemical_formula_sum            'C68 H42 F16 N10 O2'
_chemical_formula_weight         1335.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-04-11 deposited with the CCDC.    2019-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.147(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.5164(10)
_cell_length_b                   29.4938(10)
_cell_length_c                   10.7214(4)
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      66.53
_cell_measurement_theta_min      3.25
_cell_volume                     8590.4(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'narrow frame ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            32028
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.786
_diffrn_reflns_theta_max         66.786
_diffrn_reflns_theta_min         2.211
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5739
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.032
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             2720
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         7570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0548
_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)+(0.1078P)²+6.5032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1631
_refine_ls_wR_factor_ref         0.1735
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6218
_reflns_number_total             7570
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc03932e3.cif
_cod_data_source_block           P108D_XW143_sq
_cod_database_code               7123829
_shelx_shelxl_version_number     2014/7
_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   0.701
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C 0.12159(8) 0.21309(7) 0.53082(18) 0.0404(5) Uani 1 1 d . .
C2 C 0.14584(8) 0.25411(7) 0.54999(19) 0.0432(5) Uani 1 1 d . .
C3 C 0.17899(8) 0.26956(7) 0.47433(19) 0.0425(5) Uani 1 1 d . .
C4 C 0.18557(8) 0.24034(7) 0.3776(2) 0.0430(5) Uani 1 1 d . .
C5 C 0.16181(8) 0.19922(7) 0.35828(18) 0.0400(4) Uani 1 1 d . .
C6 C 0.12847(7) 0.18373(6) 0.43400(17) 0.0359(4) Uani 1 1 d . .
C7 C 0.10180(7) 0.14014(6) 0.40815(16) 0.0319(4) Uani 1 1 d . .
C8 C 0.05197(7) 0.13596(6) 0.41922(16) 0.0315(4) Uani 1 1 d . .
H8 H 0.0355 0.1607 0.4510 0.038 Uiso 1 1 calc R U
C9 C 0.02645(7) 0.09642(6) 0.38462(16) 0.0293(4) Uani 1 1 d . .
H9 H -0.0072 0.0942 0.3944 0.035 Uiso 1 1 calc R U
C10 C 0.04943(6) 0.05956(5) 0.33530(15) 0.0276(4) Uani 1 1 d . .
C11 C 0.09984(7) 0.06309(6) 0.33219(17) 0.0318(4) Uani 1 1 d . .
H11 H 0.1169 0.0378 0.3053 0.038 Uiso 1 1 calc R U
C12 C 0.12549(7) 0.10239(6) 0.36717(18) 0.0346(4) Uani 1 1 d . .
H12 H 0.1597 0.1038 0.3633 0.042 Uiso 1 1 calc R U
C13 C 0.02263(6) 0.01788(5) 0.28671(16) 0.0271(4) Uani 1 1 d . .
C14 C 0.04911(6) -0.02566(6) 0.32043(16) 0.0278(4) Uani 1 1 d . .
C15 C 0.05749(6) -0.05638(6) 0.22643(16) 0.0303(4) Uani 1 1 d . .
H15 H 0.0471 -0.0490 0.1400 0.036 Uiso 1 1 calc R U
C16 C 0.08059(7) -0.09721(6) 0.25798(17) 0.0329(4) Uani 1 1 d . .
H16 H 0.0861 -0.1176 0.1931 0.040 Uiso 1 1 calc R U
C17 C 0.09590(7) -0.10888(6) 0.38391(17) 0.0322(4) Uani 1 1 d . .
C18 C 0.11882(7) -0.15402(6) 0.41566(18) 0.0366(4) Uani 1 1 d . .
C19 C 0.15550(8) -0.17106(7) 0.35441(19) 0.0413(5) Uani 1 1 d . .
C20 C 0.17483(8) -0.21383(7) 0.3781(2) 0.0450(5) Uani 1 1 d . .
C21 C 0.15938(8) -0.24310(7) 0.4648(2) 0.0454(5) Uani 1 1 d . .
C22 C 0.12292(9) -0.22567(7) 0.5273(2) 0.0458(5) Uani 1 1 d . .
C23 C 0.10337(8) -0.18278(7) 0.50437(19) 0.0409(5) Uani 1 1 d . .
C24 C 0.17935(9) -0.28921(8) 0.4875(2) 0.0537(6) Uani 1 1 d . .
C25 C 0.21856(10) -0.30957(8) 0.4382(3) 0.0613(6) Uani 1 1 d . .
H25 H 0.2368 -0.2950 0.3816 0.074 Uiso 1 1 calc R U
C26 C 0.16496(12) -0.32192(9) 0.5647(3) 0.0739(8) Uani 1 1 d . .
H26 H 0.1396 -0.3194 0.6150 0.089 Uiso 1 1 calc R U
C27 C 0.08880(7) -0.07816(6) 0.47793(17) 0.0323(4) Uani 1 1 d . .
H27 H 0.0994 -0.0855 0.5642 0.039 Uiso 1 1 calc R U
C28 C 0.06637(6) -0.03699(6) 0.44618(16) 0.0310(4) Uani 1 1 d . .
H28 H 0.0626 -0.0160 0.5111 0.037 Uiso 1 1 calc R U
C29 C 0.20474(8) 0.31341(7) 0.4942(2) 0.0471(5) Uani 1 1 d . .
C30 C 0.20844(10) 0.34121(8) 0.5973(2) 0.0570(6) Uani 1 1 d . .
H30 H 0.1943 0.3360 0.6714 0.068 Uiso 1 1 calc R U
C31 C 0.23321(10) 0.33583(8) 0.4156(3) 0.0589(6) Uani 1 1 d . .
H31 H 0.2388 0.3244 0.3361 0.071 Uiso 1 1 calc R U
C32 C 0.22195(10) 0.06008(8) 0.1523(3) 0.0587(6) Uani 1 1 d . .
H32 H 0.2299 0.0896 0.1265 0.070 Uiso 1 1 calc R U
C33 C 0.19237(15) -0.01559(9) 0.0925(3) 0.0853(10) Uani 1 1 d . .
H33A H 0.1567 -0.0189 0.0667 0.128 Uiso 1 1 calc R U
H33B H 0.2008 -0.0208 0.1837 0.128 Uiso 1 1 calc R U
H33C H 0.2095 -0.0378 0.0473 0.128 Uiso 1 1 calc R U
C34 C 0.20430(12) 0.04143(12) -0.0708(3) 0.0768(8) Uani 1 1 d . .
H34A H 0.2262 0.0215 -0.1095 0.115 Uiso 1 1 calc R U
H34B H 0.2144 0.0730 -0.0788 0.115 Uiso 1 1 calc R U
H34C H 0.1704 0.0375 -0.1137 0.115 Uiso 1 1 calc R U
F1 F 0.09053(5) 0.20181(4) 0.61096(11) 0.0506(3) Uani 1 1 d . .
F2 F 0.13556(6) 0.27970(4) 0.64676(12) 0.0580(4) Uani 1 1 d . .
F3 F 0.21627(5) 0.25132(4) 0.29702(13) 0.0581(4) Uani 1 1 d . .
F4 F 0.17088(5) 0.17443(4) 0.25903(11) 0.0499(3) Uani 1 1 d . .
F5 F 0.17377(5) -0.14565(4) 0.26813(12) 0.0517(3) Uani 1 1 d . .
F6 F 0.21007(5) -0.22669(5) 0.31143(13) 0.0583(4) Uani 1 1 d . .
F7 F 0.10520(6) -0.25070(4) 0.61507(13) 0.0589(4) Uani 1 1 d . .
F8 F 0.06749(5) -0.16981(4) 0.56805(12) 0.0504(3) Uani 1 1 d . .
N1 N 0.22682(10) -0.35141(7) 0.4803(2) 0.0725(7) Uani 1 1 d . .
N2 N 0.19378(11) -0.35832(8) 0.5555(3) 0.0821(8) Uani 1 1 d . .
H2 H 0.1909 -0.3840 0.5954 0.098 Uiso 1 1 calc R U
N3 N 0.23552(8) 0.37712(6) 0.5749(2) 0.0588(5) Uani 1 1 d . .
H3 H 0.2421 0.4000 0.6277 0.067(8) Uiso 1 1 calc R .
N4 N 0.25144(9) 0.37460(7) 0.4645(2) 0.0659(6) Uani 1 1 d . .
N5 N 0.20728(8) 0.02997(7) 0.0626(2) 0.0619(5) Uani 1 1 d . .
O1 O 0.22611(7) 0.05285(6) 0.26613(19) 0.0693(5) 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 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
F1 C1 C2 117.53(18) .
F1 C1 C6 119.94(16) .
C2 C1 C6 122.53(19) .
F2 C2 C1 116.69(18) .
F2 C2 C3 120.18(17) .
C1 C2 C3 123.13(19) .
C4 C3 C2 114.19(17) .
C4 C3 C29 122.56(19) .
C2 C3 C29 123.24(19) .
F3 C4 C5 116.64(18) .
F3 C4 C3 120.27(17) .
C5 C4 C3 123.09(19) .
F4 C5 C4 116.97(17) .
F4 C5 C6 120.25(16) .
C4 C5 C6 122.75(19) .
C1 C6 C5 114.30(17) .
C1 C6 C7 123.91(17) .
C5 C6 C7 121.76(17) .
C12 C7 C8 117.97(16) .
C12 C7 C6 120.52(17) .
C8 C7 C6 121.47(16) .
C9 C8 C7 120.96(16) .
C9 C8 H8 119.5 .
C7 C8 H8 119.5 .
C8 C9 C10 121.01(16) .
C8 C9 H9 119.5 .
C10 C9 H9 119.5 .
C11 C10 C9 117.40(15) .
C11 C10 C13 119.54(15) .
C9 C10 C13 123.06(15) .
C12 C11 C10 121.59(16) .
C12 C11 H11 119.2 .
C10 C11 H11 119.2 .
C11 C12 C7 120.80(17) .
C11 C12 H12 119.6 .
C7 C12 H12 119.6 .
C13 C13 C10 124.04(9) 2
C13 C13 C14 120.39(9) 2
C10 C13 C14 115.56(15) .
C28 C14 C15 118.03(15) .
C28 C14 C13 121.17(15) .
C15 C14 C13 120.80(15) .
C16 C15 C14 120.70(16) .
C16 C15 H15 119.7 .
C14 C15 H15 119.7 .
C15 C16 C17 120.71(16) .
C15 C16 H16 119.6 .
C17 C16 H16 119.6 .
C27 C17 C16 119.05(16) .
C27 C17 C18 121.30(16) .
C16 C17 C18 119.65(16) .
C19 C18 C23 115.38(17) .
C19 C18 C17 122.06(17) .
C23 C18 C17 122.50(16) .
F5 C19 C20 117.40(17) .
F5 C19 C18 120.24(17) .
C20 C19 C18 122.35(19) .
F6 C20 C19 116.73(19) .
F6 C20 C21 120.30(18) .
C19 C20 C21 122.97(18) .
C20 C21 C22 114.53(18) .
C20 C21 C24 122.7(2) .
C22 C21 C24 122.7(2) .
F7 C22 C23 116.89(18) .
F7 C22 C21 120.19(18) .
C23 C22 C21 122.91(19) .
F8 C23 C22 117.87(18) .
F8 C23 C18 120.25(17) .
C22 C23 C18 121.85(18) .
C26 C24 C25 103.8(2) .
C26 C24 C21 127.9(2) .
C25 C24 C21 128.3(2) .
N1 C25 C24 111.7(3) .
N1 C25 H25 124.1 .
C24 C25 H25 124.1 .
N2 C26 C24 106.6(3) .
N2 C26 H26 126.7 .
C24 C26 H26 126.7 .
C28 C27 C17 120.19(16) .
C28 C27 H27 119.9 .
C17 C27 H27 119.9 .
C27 C28 C14 121.24(16) .
C27 C28 H28 119.4 .
C14 C28 H28 119.4 .
C30 C29 C31 103.09(19) .
C30 C29 C3 128.0(2) .
C31 C29 C3 128.9(2) .
N3 C30 C29 107.5(2) .
N3 C30 H30 126.2 .
C29 C30 H30 126.2 .
N4 C31 C29 112.4(2) .
N4 C31 H31 123.8 .
C29 C31 H31 123.8 .
O1 C32 N5 125.2(2) .
O1 C32 H32 117.4 .
N5 C32 H32 117.4 .
N5 C33 H33A 109.5 .
N5 C33 H33B 109.5 .
H33A C33 H33B 109.5 .
N5 C33 H33C 109.5 .
H33A C33 H33C 109.5 .
H33B C33 H33C 109.5 .
N5 C34 H34A 109.5 .
N5 C34 H34B 109.5 .
H34A C34 H34B 109.5 .
N5 C34 H34C 109.5 .
H34A C34 H34C 109.5 .
H34B C34 H34C 109.5 .
C25 N1 N2 104.7(2) .
N1 N2 C26 113.0(2) .
N1 N2 H2 123.5 .
C26 N2 H2 123.5 .
N4 N3 C30 112.8(2) .
N4 N3 H3 123.6 .
C30 N3 H3 123.6 .
C31 N4 N3 104.1(2) .
C32 N5 C33 121.6(2) .
C32 N5 C34 121.3(2) .
C33 N5 C34 117.1(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 F1 1.347(2) .
C1 C2 1.381(3) .
C1 C6 1.388(3) .
C2 F2 1.349(2) .
C2 C3 1.390(3) .
C3 C4 1.382(3) .
C3 C29 1.474(3) .
C4 F3 1.341(2) .
C4 C5 1.378(3) .
C5 F4 1.347(2) .
C5 C6 1.395(3) .
C6 C7 1.485(2) .
C7 C12 1.396(3) .
C7 C8 1.400(3) .
C8 C9 1.381(2) .
C8 H8 0.9500 .
C9 C10 1.403(2) .
C9 H9 0.9500 .
C10 C11 1.397(2) .
C10 C13 1.485(2) .
C11 C12 1.378(3) .
C11 H11 0.9500 .
C12 H12 0.9500 .
C13 C13 1.363(4) 2
C13 C14 1.492(2) .
C14 C28 1.397(2) .
C14 C15 1.401(2) .
C15 C16 1.378(2) .
C15 H15 0.9500 .
C16 C17 1.392(3) .
C16 H16 0.9500 .
C17 C27 1.392(3) .
C17 C18 1.489(2) .
C18 C19 1.383(3) .
C18 C23 1.390(3) .
C19 F5 1.348(2) .
C19 C20 1.377(3) .
C20 F6 1.347(2) .
C20 C21 1.384(3) .
C21 C22 1.391(3) .
C21 C24 1.472(3) .
C22 F7 1.347(2) .
C22 C23 1.381(3) .
C23 F8 1.342(2) .
C24 C26 1.370(4) .
C24 C25 1.409(3) .
C25 N1 1.321(3) .
C25 H25 0.9500 .
C26 N2 1.348(3) .
C26 H26 0.9500 .
C27 C28 1.380(2) .
C27 H27 0.9500 .
C28 H28 0.9500 .
C29 C30 1.367(3) .
C29 C31 1.404(3) .
C30 N3 1.338(3) .
C30 H30 0.9500 .
C31 N4 1.323(3) .
C31 H31 0.9500 .
C32 O1 1.226(3) .
C32 N5 1.324(3) .
C32 H32 0.9500 .
C33 N5 1.456(4) .
C33 H33A 0.9800 .
C33 H33B 0.9800 .
C33 H33C 0.9800 .
C34 N5 1.459(4) .
C34 H34A 0.9800 .
C34 H34B 0.9800 .
C34 H34C 0.9800 .
N1 N2 1.323(4) .
N2 H2 0.8800 .
N3 N4 1.328(3) .
N3 H3 0.8800 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168350830
