#------------------------------------------------------------------------------
#$Date: 2023-09-05 23:26:17 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286197 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/71/7247121.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_7247121
loop_
_publ_author_name
'Camargo, Bruno'
'Zajcewa, Irina'
'Pietrzak, Anna'
'Obijalska, Emilia'
'Szczytko, Jacek'
'Kaszyński, Piotr'
_publ_section_title
;
 Thermally induced dimensionality changes in derivatives of a "super
 stable" Blatter radical.
;
_journal_issue                   34
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              22813
_journal_page_last               22818
_journal_paper_doi               10.1039/d3cp01298k
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C21 H12 F6 N3'
_chemical_formula_sum            'C21 H12 F6 N3'
_chemical_formula_weight         420.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     other
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-04-29 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                87.499(3)
_cell_angle_beta                 78.856(2)
_cell_angle_gamma                66.8720(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9593(2)
_cell_length_b                   9.5462(2)
_cell_length_c                   13.0766(3)
_cell_measurement_reflns_used    15659
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      78.3840
_cell_measurement_theta_min      3.4000
_cell_volume                     895.92(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      99.9(4)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20833
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.194
_diffrn_reflns_theta_min         3.447
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.206
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_description       block
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3585
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0326
_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)+(0.0446P)²+0.3549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3270
_reflns_number_total             3585
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cp01298k2.cif
_cod_data_source_block           PB_rad_2CF3_manual
_cod_depositor_comments
'Adding full bibliography for 7247120--7247121.cif.'
_cod_database_code               7247121
_shelx_shelxl_version_number     2018/3
_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.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.606
_oxdiff_exptl_absorpt_empirical_full_max 2.213
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
F1 F 0.12262(11) 0.80718(11) 0.82412(7) 0.0435(2) Uani 1 1 d . . . . .
N1 N 0.40929(14) 0.60016(11) 0.68260(8) 0.0182(2) Uani 1 1 d . . . . .
C1 C 0.35248(16) 0.48096(13) 0.67911(9) 0.0166(2) Uani 1 1 d . . . . .
F2 F 0.15910(12) 0.81919(11) 0.98043(7) 0.0449(3) Uani 1 1 d . . . . .
N2 N 0.22312(14) 0.59613(11) 0.52711(7) 0.0173(2) Uani 1 1 d . . . . .
C2 C 0.38561(16) 0.36506(13) 0.75105(9) 0.0177(2) Uani 1 1 d . . . . .
H2 H 0.449700 0.364238 0.803623 0.021 Uiso 1 1 calc R U . . .
F3 F 0.15966(11) 0.61469(9) 0.91952(7) 0.0341(2) Uani 1 1 d . . . . .
C3 C 0.32134(16) 0.25159(13) 0.74264(9) 0.0174(2) Uani 1 1 d . . . . .
F4 F 0.48288(11) 0.10895(9) 0.87180(6) 0.02936(19) Uani 1 1 d . . . . .
C4 C 0.22905(17) 0.24927(13) 0.66217(9) 0.0189(2) Uani 1 1 d . . . . .
H4 H 0.188988 0.171016 0.656810 0.023 Uiso 1 1 calc R U . . .
F5 F 0.18659(12) 0.17886(10) 0.90084(6) 0.0379(2) Uani 1 1 d . . . . .
C5 C 0.19759(16) 0.36336(13) 0.59077(9) 0.0186(2) Uani 1 1 d . . . . .
H5 H 0.136018 0.361449 0.537545 0.022 Uiso 1 1 calc R U . . .
F6 F 0.35858(12) -0.00002(8) 0.78676(6) 0.0316(2) Uani 1 1 d . . . . .
C6 C 0.25753(16) 0.48236(13) 0.59759(9) 0.0162(2) Uani 1 1 d . . . . .
C7 C 0.28672(16) 0.70395(13) 0.53937(9) 0.0157(2) Uani 1 1 d . . . . .
C8 C 0.25226(15) 0.82936(13) 0.46445(9) 0.0163(2) Uani 1 1 d . . . . .
N009 N 0.38032(14) 0.71287(11) 0.61211(8) 0.0179(2) Uani 1 1 d . . . . .
C9 C 0.15747(17) 0.83044(14) 0.38508(10) 0.0207(3) Uani 1 1 d . . . . .
H9 H 0.116129 0.752963 0.379689 0.025 Uiso 1 1 calc R U . . .
C10 C 0.12419(18) 0.94576(15) 0.31409(10) 0.0243(3) Uani 1 1 d . . . . .
H10 H 0.060723 0.945416 0.261447 0.029 Uiso 1 1 calc R U . . .
C11 C 0.18561(18) 1.06195(14) 0.32151(10) 0.0227(3) Uani 1 1 d . . . . .
H11 H 0.163159 1.139526 0.274016 0.027 Uiso 1 1 calc R U . . .
C12 C 0.28050(18) 1.06172(14) 0.40004(10) 0.0218(3) Uani 1 1 d . . . . .
H12 H 0.322308 1.139038 0.404918 0.026 Uiso 1 1 calc R U . . .
C13 C 0.31334(17) 0.94644(14) 0.47143(9) 0.0191(2) Uani 1 1 d . . . . .
H13 H 0.376380 0.947310 0.524165 0.023 Uiso 1 1 calc R U . . .
C14 C 0.51318(17) 0.61127(13) 0.75859(9) 0.0168(2) Uani 1 1 d . . . . .
C15 C 0.70425(17) 0.56237(13) 0.72797(9) 0.0194(2) Uani 1 1 d . . . . .
H15 H 0.761645 0.523625 0.660446 0.023 Uiso 1 1 calc R U . . .
C16 C 0.81044(18) 0.57140(14) 0.79872(10) 0.0216(3) Uani 1 1 d . . . . .
H16 H 0.938993 0.538118 0.778587 0.026 Uiso 1 1 calc R U . . .
C17 C 0.72425(18) 0.63001(15) 0.89902(10) 0.0227(3) Uani 1 1 d . . . . .
H17 H 0.795227 0.635736 0.946215 0.027 Uiso 1 1 calc R U . . .
C18 C 0.53295(18) 0.68007(14) 0.92930(9) 0.0215(3) Uani 1 1 d . . . . .
H18 H 0.476077 0.719686 0.996686 0.026 Uiso 1 1 calc R U . . .
C19 C 0.42487(17) 0.67158(13) 0.85954(9) 0.0184(2) Uani 1 1 d . . . . .
C20 C 0.21706(18) 0.72887(14) 0.89584(10) 0.0220(3) Uani 1 1 d . . . . .
C21 C 0.33870(18) 0.13450(14) 0.82473(9) 0.0216(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 0.0181 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'
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
N009 N1 C1 123.39(9) . . ?
N009 N1 C14 114.07(9) . . ?
C1 N1 C14 122.47(9) . . ?
N1 C1 C2 122.72(10) . . ?
N1 C1 C6 116.09(10) . . ?
C2 C1 C6 121.20(10) . . ?
C7 N2 C6 115.95(10) . . ?
C3 C2 C1 118.82(10) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 121.14(11) . . ?
C2 C3 C21 119.85(10) . . ?
C4 C3 C21 118.88(10) . . ?
C5 C4 C3 119.91(10) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.80(11) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
N2 C6 C5 120.24(10) . . ?
N2 C6 C1 121.65(10) . . ?
C5 C6 C1 118.11(10) . . ?
N2 C7 N009 127.53(11) . . ?
N2 C7 C8 117.60(10) . . ?
N009 C7 C8 114.87(10) . . ?
C9 C8 C13 118.93(11) . . ?
C9 C8 C7 119.59(10) . . ?
C13 C8 C7 121.48(10) . . ?
C7 N009 N1 115.37(9) . . ?
C10 C9 C8 120.68(11) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.04(11) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 119.73(11) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.26(11) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.36(11) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C15 C14 C19 120.69(10) . . ?
C15 C14 N1 117.72(10) . . ?
C19 C14 N1 121.58(11) . . ?
C14 C15 C16 119.75(11) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 119.93(12) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 120.27(11) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 120.50(11) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 118.86(11) . . ?
C18 C19 C20 118.52(11) . . ?
C14 C19 C20 122.62(10) . . ?
F2 C20 F1 106.89(11) . . ?
F2 C20 F3 106.68(10) . . ?
F1 C20 F3 105.64(10) . . ?
F2 C20 C19 112.05(10) . . ?
F1 C20 C19 113.00(10) . . ?
F3 C20 C19 112.10(10) . . ?
F6 C21 F4 107.06(10) . . ?
F6 C21 F5 106.53(10) . . ?
F4 C21 F5 105.99(10) . . ?
F6 C21 C3 112.54(10) . . ?
F4 C21 C3 113.07(10) . . ?
F5 C21 C3 111.20(10) . . ?
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
F1 C20 1.3316(15) . ?
N1 N009 1.3642(14) . ?
N1 C1 1.3849(14) . ?
N1 C14 1.4415(14) . ?
C1 C2 1.3981(16) . ?
C1 C6 1.4177(16) . ?
F2 C20 1.3241(15) . ?
N2 C7 1.3403(15) . ?
N2 C6 1.3713(15) . ?
C2 C3 1.3836(16) . ?
C2 H2 0.9300 . ?
F3 C20 1.3416(14) . ?
C3 C4 1.4004(16) . ?
C3 C21 1.5007(16) . ?
F4 C21 1.3399(14) . ?
C4 C5 1.3814(17) . ?
C4 H4 0.9300 . ?
F5 C21 1.3431(15) . ?
C5 C6 1.4060(16) . ?
C5 H5 0.9300 . ?
F6 C21 1.3365(14) . ?
C7 N009 1.3409(15) . ?
C7 C8 1.4872(16) . ?
C8 C9 1.3937(16) . ?
C8 C13 1.3953(16) . ?
C9 C10 1.3859(17) . ?
C9 H9 0.9300 . ?
C10 C11 1.3902(17) . ?
C10 H10 0.9300 . ?
C11 C12 1.3867(17) . ?
C11 H11 0.9300 . ?
C12 C13 1.3891(17) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.3836(17) . ?
C14 C19 1.3992(17) . ?
C15 C16 1.3944(17) . ?
C15 H15 0.9300 . ?
C16 C17 1.3852(18) . ?
C16 H16 0.9300 . ?
C17 C18 1.3840(18) . ?
C17 H17 0.9300 . ?
C18 C19 1.3940(16) . ?
C18 H18 0.9300 . ?
C19 C20 1.5062(17) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N009 N1 C1 C2 179.04(11) . . . . ?
C14 N1 C1 C2 2.29(18) . . . . ?
N009 N1 C1 C6 -0.95(17) . . . . ?
C14 N1 C1 C6 -177.70(10) . . . . ?
N1 C1 C2 C3 179.01(11) . . . . ?
C6 C1 C2 C3 -1.00(17) . . . . ?
C1 C2 C3 C4 1.73(18) . . . . ?
C1 C2 C3 C21 -174.11(11) . . . . ?
C2 C3 C4 C5 -1.32(18) . . . . ?
C21 C3 C4 C5 174.56(11) . . . . ?
C3 C4 C5 C6 0.13(18) . . . . ?
C7 N2 C6 C5 -179.52(10) . . . . ?
C7 N2 C6 C1 0.84(16) . . . . ?
C4 C5 C6 N2 -179.07(11) . . . . ?
C4 C5 C6 C1 0.58(17) . . . . ?
N1 C1 C6 N2 -0.51(16) . . . . ?
C2 C1 C6 N2 179.50(11) . . . . ?
N1 C1 C6 C5 179.85(10) . . . . ?
C2 C1 C6 C5 -0.15(17) . . . . ?
C6 N2 C7 N009 0.27(18) . . . . ?
C6 N2 C7 C8 179.98(9) . . . . ?
N2 C7 C8 C9 -0.29(16) . . . . ?
N009 C7 C8 C9 179.45(11) . . . . ?
N2 C7 C8 C13 179.93(11) . . . . ?
N009 C7 C8 C13 -0.32(16) . . . . ?
N2 C7 N009 N1 -1.61(18) . . . . ?
C8 C7 N009 N1 178.67(9) . . . . ?
C1 N1 N009 C7 1.92(16) . . . . ?
C14 N1 N009 C7 178.92(10) . . . . ?
C13 C8 C9 C10 0.00(18) . . . . ?
C7 C8 C9 C10 -179.78(11) . . . . ?
C8 C9 C10 C11 0.0(2) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C10 C11 C12 C13 -0.35(19) . . . . ?
C11 C12 C13 C8 0.40(19) . . . . ?
C9 C8 C13 C12 -0.22(18) . . . . ?
C7 C8 C13 C12 179.55(11) . . . . ?
N009 N1 C14 C15 -78.42(13) . . . . ?
C1 N1 C14 C15 98.60(13) . . . . ?
N009 N1 C14 C19 100.54(13) . . . . ?
C1 N1 C14 C19 -82.44(15) . . . . ?
C19 C14 C15 C16 0.81(17) . . . . ?
N1 C14 C15 C16 179.79(10) . . . . ?
C14 C15 C16 C17 -0.37(18) . . . . ?
C15 C16 C17 C18 -0.17(19) . . . . ?
C16 C17 C18 C19 0.28(19) . . . . ?
C17 C18 C19 C14 0.15(17) . . . . ?
C17 C18 C19 C20 -179.43(11) . . . . ?
C15 C14 C19 C18 -0.70(17) . . . . ?
N1 C14 C19 C18 -179.64(10) . . . . ?
C15 C14 C19 C20 178.86(11) . . . . ?
N1 C14 C19 C20 -0.07(17) . . . . ?
C18 C19 C20 F2 17.90(16) . . . . ?
C14 C19 C20 F2 -161.67(11) . . . . ?
C18 C19 C20 F1 138.73(12) . . . . ?
C14 C19 C20 F1 -40.84(16) . . . . ?
C18 C19 C20 F3 -102.02(13) . . . . ?
C14 C19 C20 F3 78.41(14) . . . . ?
C2 C3 C21 F6 -149.61(11) . . . . ?
C4 C3 C21 F6 34.45(15) . . . . ?
C2 C3 C21 F4 -28.15(16) . . . . ?
C4 C3 C21 F4 155.91(11) . . . . ?
C2 C3 C21 F5 90.95(13) . . . . ?
C4 C3 C21 F5 -84.98(13) . . . . ?
