#------------------------------------------------------------------------------
#$Date: 2022-05-19 00:57:56 +0300 (Thu, 19 May 2022) $
#$Revision: 275523 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/01/7130120.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_7130120
loop_
_publ_author_name
'Kocsi, Daniel'
'Orthaber, Andreas'
'Borbas, Eszter'
_publ_section_title
;
 Tuning the photophysical properties of luminescent lanthanide complexes
 through regioselective antenna fluorination
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01229D
_journal_year                    2022
_chemical_formula_moiety         'C9 H7 F N2 O'
_chemical_formula_sum            'C9 H7 F N2 O'
_chemical_formula_weight         178.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-22
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-02-27 deposited with the CCDC.	2022-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.160(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2349(8)
_cell_length_b                   8.1302(13)
_cell_length_c                   18.418(3)
_cell_measurement_reflns_used    3582
_cell_measurement_temperature    180
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      2.74
_cell_volume                     783.7(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13765
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.917
_diffrn_reflns_theta_min         2.212
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1558 before and 0.0387 after correction.
The Ratio of minimum to maximum transmission is 0.9073.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         2051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0444
_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)+(0.0626P)²+0.3863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1385
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1564
_reflns_number_total             2051
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc01229d2.cif
_cod_data_source_block           ao_keb_dk_30e_1_0m
_cod_database_code               7130120
_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.
;
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C6(H6), C5(H5), C4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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 0.6520(2) 0.20615(14) 0.44877(6) 0.0438(3) Uani 1 1 d . . . . .
O1 O 0.2333(2) 0.40626(15) 0.44394(6) 0.0334(3) Uani 1 1 d . . . . .
N1 N 0.1712(2) 0.36459(16) 0.56462(6) 0.0258(3) Uani 1 1 d . . . . .
H1 H 0.035320 0.428212 0.561973 0.031 Uiso 1 1 calc R U . . .
N2 N 0.0197(3) 0.3078(2) 0.82099(8) 0.0350(4) Uani 1 1 d . . . . .
C9 C 0.2355(3) 0.29785(18) 0.63198(8) 0.0237(3) Uani 1 1 d . . . . .
C10 C 0.4513(3) 0.19454(18) 0.63754(8) 0.0253(3) Uani 1 1 d . . . . .
C8 C 0.0877(3) 0.33376(19) 0.69236(8) 0.0257(3) Uani 1 1 d . . . . .
H8 H -0.058375 0.402418 0.687262 0.031 Uiso 1 1 calc R U . . .
C7 C 0.1554(3) 0.26853(19) 0.76009(8) 0.0266(3) Uani 1 1 d . . . . .
C2 C 0.3016(3) 0.33940(19) 0.50238(8) 0.0270(3) Uani 1 1 d . . . . .
C6 C 0.3751(3) 0.1672(2) 0.76648(8) 0.0297(4) Uani 1 1 d . . . . .
H6 H 0.424241 0.123699 0.812553 0.036 Uiso 1 1 calc R U . . .
C5 C 0.5170(3) 0.1315(2) 0.70690(9) 0.0295(3) Uani 1 1 d . . . . .
H5 H 0.662885 0.062711 0.712314 0.035 Uiso 1 1 calc R U . . .
C3 C 0.5198(3) 0.2320(2) 0.51023(9) 0.0301(4) Uani 1 1 d . . . . .
C4 C 0.5924(3) 0.16208(19) 0.57372(9) 0.0294(3) Uani 1 1 d . . . . .
H4 H 0.736927 0.091467 0.575913 0.035 Uiso 1 1 calc R U . . .
H2A H 0.056(4) 0.247(2) 0.8604(11) 0.035 Uiso 1 1 d . U . . .
H2B H -0.139(4) 0.350(3) 0.8130(12) 0.048(6) Uiso 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C9 N1 H1 117.4 . . ?
C2 N1 H1 117.4 . . ?
C2 N1 C9 125.21(13) . . ?
C7 N2 H2A 115.3(13) . . ?
C7 N2 H2B 116.2(14) . . ?
H2A N2 H2B 121.2(19) . . ?
N1 C9 C10 118.48(13) . . ?
N1 C9 C8 120.05(14) . . ?
C8 C9 C10 121.47(13) . . ?
C9 C10 C5 117.51(14) . . ?
C9 C10 C4 118.57(14) . . ?
C5 C10 C4 123.91(14) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 C9 119.83(14) . . ?
C7 C8 H8 120.1 . . ?
N2 C7 C8 120.96(15) . . ?
N2 C7 C6 119.87(14) . . ?
C8 C7 C6 119.09(14) . . ?
O1 C2 N1 121.30(15) . . ?
O1 C2 C3 124.12(14) . . ?
N1 C2 C3 114.59(13) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 C7 120.62(14) . . ?
C5 C6 H6 119.7 . . ?
C10 C5 H5 119.3 . . ?
C6 C5 C10 121.45(15) . . ?
C6 C5 H5 119.3 . . ?
F1 C3 C2 115.29(14) . . ?
C4 C3 F1 121.27(15) . . ?
C4 C3 C2 123.44(14) . . ?
C10 C4 H4 120.1 . . ?
C3 C4 C10 119.70(15) . . ?
C3 C4 H4 120.1 . . ?
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 C3 1.3553(18) . ?
O1 C2 1.2515(19) . ?
N1 H1 0.8800 . ?
N1 C9 1.3892(18) . ?
N1 C2 1.3616(19) . ?
N2 C7 1.377(2) . ?
N2 H2A 0.90(2) . ?
N2 H2B 0.91(2) . ?
C9 C10 1.410(2) . ?
C9 C8 1.398(2) . ?
C10 C5 1.412(2) . ?
C10 C4 1.425(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.394(2) . ?
C7 C6 1.418(2) . ?
C2 C3 1.443(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.369(2) . ?
C5 H5 0.9500 . ?
C3 C4 1.348(2) . ?
C4 H4 0.9500 . ?
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
F1 C3 C4 C10 178.84(14) . . . . ?
O1 C2 C3 F1 0.0(2) . . . . ?
O1 C2 C3 C4 179.36(16) . . . . ?
N1 C9 C10 C5 178.42(13) . . . . ?
N1 C9 C10 C4 -0.5(2) . . . . ?
N1 C9 C8 C7 -179.01(13) . . . . ?
N1 C2 C3 F1 -179.80(13) . . . . ?
N1 C2 C3 C4 -0.4(2) . . . . ?
N2 C7 C6 C5 -177.80(15) . . . . ?
C9 N1 C2 O1 -178.87(14) . . . . ?
C9 N1 C2 C3 0.9(2) . . . . ?
C9 C10 C5 C6 0.8(2) . . . . ?
C9 C10 C4 C3 1.0(2) . . . . ?
C9 C8 C7 N2 177.10(14) . . . . ?
C9 C8 C7 C6 0.4(2) . . . . ?
C10 C9 C8 C7 0.9(2) . . . . ?
C8 C9 C10 C5 -1.5(2) . . . . ?
C8 C9 C10 C4 179.54(14) . . . . ?
C8 C7 C6 C5 -1.0(2) . . . . ?
C7 C6 C5 C10 0.4(2) . . . . ?
C2 N1 C9 C10 -0.4(2) . . . . ?
C2 N1 C9 C8 179.47(14) . . . . ?
C2 C3 C4 C10 -0.5(3) . . . . ?
C5 C10 C4 C3 -177.89(15) . . . . ?
C4 C10 C5 C6 179.73(15) . . . . ?
