#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/19/7121952.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_7121952
loop_
_publ_author_name
'Thomson, Connor J.'
'Zhang, Qingzhi'
'Al-Maharik, Nawaf'
'Bühl, Michael'
'Cordes, David B.'
'Slawin, Alexandra M. Z.'
'O'Hagan, David'
_publ_section_title
;
 Fluorinated cyclopropanes: synthesis and chemistry of the aryl
 α,β,β-trifluorocyclopropane motif.
;
_journal_issue                   60
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8415
_journal_page_last               8418
_journal_paper_doi               10.1039/c8cc04964e
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C11 H10 F3 N O'
_chemical_formula_sum            'C11 H10 F3 N O'
_chemical_formula_weight         229.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-06-25
_audit_creation_method           'by CrystalStructure 4.3'
_audit_update_record
;
2018-06-25 deposited with the CCDC.
2018-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   21.421(6)
_cell_length_b                   8.828(2)
_cell_length_c                   11.037(3)
_cell_measurement_reflns_used    2270
_cell_measurement_temperature    173
_cell_measurement_theta_max      24.30
_cell_measurement_theta_min      2.60
_cell_volume                     2087.1(9)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24311
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         1.901
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             944.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/petroleum ether'
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.15
_refine_ls_abs_structure_details
;
 Flack x determined using 1020 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3681
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0305P)²+0.2203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0774
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                2784
_reflns_number_total             3681
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c8cc04964e2.cif
_cod_data_source_block           19b
_cod_depositor_comments
'Adding full bibliography for 7121950--7121954.cif.'
_cod_database_code               7121952
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,1/2+Z
3 1/2-X,+Y,1/2+Z
4 1/2+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
F1 F -0.02822(9) 0.3466(2) 0.19240(18) 0.0414(5) Uani 1 1 d . .
F2 F -0.09919(11) 0.3570(3) -0.0097(2) 0.0644(7) Uani 1 1 d . .
F3 F -0.03682(13) 0.5185(3) -0.0973(2) 0.0746(8) Uani 1 1 d . .
F21 F -0.00897(10) -0.1654(3) 0.2719(2) 0.0494(6) Uani 1 1 d . .
F22 F -0.01636(11) -0.1406(3) 0.5127(2) 0.0599(7) Uani 1 1 d . .
F23 F 0.05863(11) 0.0260(3) 0.5225(2) 0.0575(7) Uani 1 1 d . .
O4 O 0.05884(11) 0.6428(3) 0.0604(2) 0.0391(6) Uani 1 1 d . .
O24 O 0.09867(11) 0.1375(3) 0.2824(2) 0.0379(6) Uani 1 1 d . .
N5 N 0.09004(13) 0.4249(3) 0.1514(2) 0.0302(7) Uani 1 1 d D .
H5 H 0.0760(17) 0.342(3) 0.194(3) 0.048(12) Uiso 1 1 d D .
N25 N 0.10078(13) -0.0859(3) 0.1798(3) 0.0327(7) Uani 1 1 d D .
H25 H 0.0786(15) -0.174(3) 0.156(3) 0.043(11) Uiso 1 1 d D .
C1 C -0.01868(16) 0.4675(4) 0.1171(3) 0.0309(8) Uani 1 1 d . .
C2 C -0.05967(19) 0.4733(5) 0.0095(4) 0.0454(10) Uani 1 1 d . .
C3 C -0.07206(19) 0.5801(5) 0.1073(4) 0.0548(11) Uani 1 1 d . .
H3A H -0.109441 0.562583 0.158151 0.066 Uiso 1 1 calc R U
H3B H -0.061444 0.687846 0.093609 0.066 Uiso 1 1 calc R U
C4 C 0.04733(16) 0.5197(4) 0.1081(3) 0.0292(8) Uani 1 1 d . .
C6 C 0.15652(15) 0.4558(4) 0.1423(3) 0.0353(9) Uani 1 1 d . .
H6A H 0.176625 0.430363 0.220466 0.042 Uiso 1 1 calc R U
H6B H 0.162598 0.565535 0.127952 0.042 Uiso 1 1 calc R U
C7 C 0.18844(16) 0.3684(4) 0.0423(3) 0.0298(8) Uani 1 1 d . .
C8 C 0.15623(17) 0.3093(4) -0.0555(3) 0.0356(9) Uani 1 1 d . .
H8 H 0.112427 0.324262 -0.061640 0.043 Uiso 1 1 calc R U
C9 C 0.1873(2) 0.2287(5) -0.1446(3) 0.0448(10) Uani 1 1 d . .
H9 H 0.164577 0.186899 -0.210575 0.054 Uiso 1 1 calc R U
C10 C 0.2513(2) 0.2086(4) -0.1379(4) 0.0448(10) Uani 1 1 d . .
H10 H 0.272667 0.153298 -0.198994 0.054 Uiso 1 1 calc R U
C11 C 0.28363(19) 0.2696(5) -0.0419(4) 0.0478(11) Uani 1 1 d . .
H11 H 0.327643 0.257619 -0.037324 0.057 Uiso 1 1 calc R U
C12 C 0.25257(18) 0.3480(4) 0.0479(4) 0.0396(9) Uani 1 1 d . .
H12 H 0.275364 0.388397 0.114287 0.047 Uiso 1 1 calc R U
C21 C 0.01834(16) -0.0383(4) 0.3204(3) 0.0329(9) Uani 1 1 d . .
C22 C 0.01141(19) -0.0251(5) 0.4538(3) 0.0430(10) Uani 1 1 d . .
C23 C -0.02587(19) 0.0753(4) 0.3785(3) 0.0413(10) Uani 1 1 d . .
H23A H -0.014100 0.183652 0.375868 0.050 Uiso 1 1 calc R U
H23B H -0.071240 0.055143 0.372808 0.050 Uiso 1 1 calc R U
C24 C 0.07626(15) 0.0133(4) 0.2576(3) 0.0297(8) Uani 1 1 d . .
C26 C 0.16116(15) -0.0603(4) 0.1222(3) 0.0352(9) Uani 1 1 d . .
H26A H 0.168483 0.050145 0.116232 0.042 Uiso 1 1 calc R U
H26B H 0.159728 -0.101331 0.038743 0.042 Uiso 1 1 calc R U
C27 C 0.21523(16) -0.1316(4) 0.1884(3) 0.0300(8) Uani 1 1 d . .
C28 C 0.20821(17) -0.2150(4) 0.2939(3) 0.0359(9) Uani 1 1 d . .
H28 H 0.167866 -0.227167 0.328315 0.043 Uiso 1 1 calc R U
C29 C 0.2597(2) -0.2812(4) 0.3501(4) 0.0446(10) Uani 1 1 d . .
H29 H 0.254086 -0.339314 0.421730 0.054 Uiso 1 1 calc R U
C30 C 0.31836(19) -0.2629(5) 0.3026(4) 0.0459(11) Uani 1 1 d . .
H30 H 0.353338 -0.308781 0.340739 0.055 Uiso 1 1 calc R U
C31 C 0.32622(18) -0.1775(5) 0.1993(4) 0.0479(11) Uani 1 1 d . .
H31 H 0.366891 -0.162956 0.166977 0.057 Uiso 1 1 calc R U
C32 C 0.27535(17) -0.1128(4) 0.1423(3) 0.0398(10) Uani 1 1 d . .
H32 H 0.281407 -0.054716 0.070750 0.048 Uiso 1 1 calc R U
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(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
C4 N5 C6 122.1(3)
C4 N5 H5 117(2)
C6 N5 H5 120(2)
C24 N25 C26 121.9(3)
C24 N25 H25 121(2)
C26 N25 H25 117(2)
F1 C1 C2 115.3(3)
F1 C1 C4 115.0(3)
C2 C1 C4 120.0(3)
F1 C1 C3 116.2(3)
C2 C1 C3 58.2(3)
C4 C1 C3 120.5(3)
F3 C2 F2 108.6(3)
F3 C2 C3 121.8(4)
F2 C2 C3 119.6(4)
F3 C2 C1 120.1(3)
F2 C2 C1 118.2(3)
C3 C2 C1 62.3(3)
C2 C3 C1 59.5(3)
C2 C3 H3A 117.8
C1 C3 H3A 117.8
C2 C3 H3B 117.8
C1 C3 H3B 117.8
H3A C3 H3B 115.0
O4 C4 N5 124.8(3)
O4 C4 C1 119.4(3)
N5 C4 C1 115.8(3)
N5 C6 C7 113.4(3)
N5 C6 H6A 108.9
C7 C6 H6A 108.9
N5 C6 H6B 108.9
C7 C6 H6B 108.9
H6A C6 H6B 107.7
C8 C7 C12 118.7(3)
C8 C7 C6 122.5(3)
C12 C7 C6 118.8(3)
C7 C8 C9 120.6(3)
C7 C8 H8 119.7
C9 C8 H8 119.7
C8 C9 C10 120.2(4)
C8 C9 H9 119.9
C10 C9 H9 119.9
C11 C10 C9 119.3(4)
C11 C10 H10 120.3
C9 C10 H10 120.3
C10 C11 C12 120.4(4)
C10 C11 H11 119.8
C12 C11 H11 119.8
C11 C12 C7 120.7(4)
C11 C12 H12 119.6
C7 C12 H12 119.6
F21 C21 C22 114.1(3)
F21 C21 C24 115.0(3)
C22 C21 C24 121.3(3)
F21 C21 C23 115.9(3)
C22 C21 C23 57.8(3)
C24 C21 C23 120.8(3)
F23 C22 F22 108.3(3)
F23 C22 C23 122.1(4)
F22 C22 C23 119.6(3)
F23 C22 C21 120.8(3)
F22 C22 C21 117.6(4)
C23 C22 C21 62.4(3)
C22 C23 C21 59.8(2)
C22 C23 H23A 117.8
C21 C23 H23A 117.8
C22 C23 H23B 117.8
C21 C23 H23B 117.8
H23A C23 H23B 114.9
O24 C24 N25 125.1(3)
O24 C24 C21 119.6(3)
N25 C24 C21 115.2(3)
N25 C26 C27 113.9(3)
N25 C26 H26A 108.8
C27 C26 H26A 108.8
N25 C26 H26B 108.8
C27 C26 H26B 108.8
H26A C26 H26B 107.7
C28 C27 C32 118.0(3)
C28 C27 C26 123.1(3)
C32 C27 C26 118.9(3)
C27 C28 C29 120.7(3)
C27 C28 H28 119.6
C29 C28 H28 119.6
C30 C29 C28 120.4(4)
C30 C29 H29 119.8
C28 C29 H29 119.8
C29 C30 C31 119.5(4)
C29 C30 H30 120.2
C31 C30 H30 120.2
C30 C31 C32 120.5(4)
C30 C31 H31 119.8
C32 C31 H31 119.8
C31 C32 C27 120.8(4)
C31 C32 H32 119.6
C27 C32 H32 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C1 1.368(4)
F2 C2 1.348(4)
F3 C2 1.337(5)
F21 C21 1.374(4)
F22 C22 1.348(4)
F23 C22 1.343(5)
O4 C4 1.233(4)
O24 C24 1.228(4)
N5 C4 1.328(4)
N5 C6 1.453(4)
N5 H5 0.92(2)
N25 C24 1.334(4)
N25 C26 1.459(4)
N25 H25 0.95(2)
C1 C2 1.478(5)
C1 C4 1.490(5)
C1 C3 1.519(5)
C2 C3 1.457(6)
C3 H3A 0.9900
C3 H3B 0.9900
C6 C7 1.510(5)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.384(5)
C7 C12 1.387(5)
C8 C9 1.384(5)
C8 H8 0.9500
C9 C10 1.385(6)
C9 H9 0.9500
C10 C11 1.376(6)
C10 H10 0.9500
C11 C12 1.379(5)
C11 H11 0.9500
C12 H12 0.9500
C21 C22 1.484(5)
C21 C24 1.492(5)
C21 C23 1.521(5)
C22 C23 1.453(5)
C23 H23A 0.9900
C23 H23B 0.9900
C26 C27 1.507(5)
C26 H26A 0.9900
C26 H26B 0.9900
C27 C28 1.386(5)
C27 C32 1.395(5)
C28 C29 1.393(5)
C28 H28 0.9500
C29 C30 1.371(6)
C29 H29 0.9500
C30 C31 1.378(6)
C30 H30 0.9500
C31 C32 1.382(5)
C31 H31 0.9500
C32 H32 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5 O24 0.92(2) 2.11(3) 2.926(4) 147(3) . yes
N25 H25 O4 0.95(2) 1.98(3) 2.878(4) 158(3) 1_545 yes
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
F1 C1 C2 F3 -141.1(3)
C4 C1 C2 F3 3.2(6)
C3 C1 C2 F3 112.6(4)
F1 C1 C2 F2 -4.3(5)
C4 C1 C2 F2 140.0(4)
C3 C1 C2 F2 -110.6(4)
F1 C1 C2 C3 106.3(4)
C4 C1 C2 C3 -109.4(4)
F3 C2 C3 C1 -109.9(4)
F2 C2 C3 C1 108.4(4)
F1 C1 C3 C2 -104.7(3)
C4 C1 C3 C2 108.5(4)
C6 N5 C4 O4 -2.3(5)
C6 N5 C4 C1 176.2(3)
F1 C1 C4 O4 -167.2(3)
C2 C1 C4 O4 48.4(5)
C3 C1 C4 O4 -20.0(5)
F1 C1 C4 N5 14.3(4)
C2 C1 C4 N5 -130.1(4)
C3 C1 C4 N5 161.4(3)
C4 N5 C6 C7 -101.9(4)
N5 C6 C7 C8 21.6(5)
N5 C6 C7 C12 -159.2(3)
C12 C7 C8 C9 1.4(5)
C6 C7 C8 C9 -179.4(3)
C7 C8 C9 C10 -1.2(6)
C8 C9 C10 C11 0.0(6)
C9 C10 C11 C12 1.0(6)
C10 C11 C12 C7 -0.8(6)
C8 C7 C12 C11 -0.4(5)
C6 C7 C12 C11 -179.6(3)
F21 C21 C22 F23 140.7(3)
C24 C21 C22 F23 -3.8(6)
C23 C21 C22 F23 -112.8(4)
F21 C21 C22 F22 4.3(5)
C24 C21 C22 F22 -140.2(4)
C23 C21 C22 F22 110.9(4)
F21 C21 C22 C23 -106.5(3)
C24 C21 C22 C23 109.0(4)
F23 C22 C23 C21 110.7(4)
F22 C22 C23 C21 -107.7(4)
F21 C21 C23 C22 103.3(4)
C24 C21 C23 C22 -109.9(4)
C26 N25 C24 O24 5.2(5)
C26 N25 C24 C21 -172.5(3)
F21 C21 C24 O24 169.1(3)
C22 C21 C24 O24 -46.7(5)
C23 C21 C24 O24 22.0(5)
F21 C21 C24 N25 -13.1(4)
C22 C21 C24 N25 131.1(4)
C23 C21 C24 N25 -160.2(3)
C24 N25 C26 C27 93.7(4)
N25 C26 C27 C28 0.5(5)
N25 C26 C27 C32 -179.1(3)
C32 C27 C28 C29 -1.7(5)
C26 C27 C28 C29 178.7(3)
C27 C28 C29 C30 1.0(5)
C28 C29 C30 C31 0.5(6)
C29 C30 C31 C32 -1.2(6)
C30 C31 C32 C27 0.4(6)
C28 C27 C32 C31 1.0(5)
C26 C27 C32 C31 -179.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139188876
