#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/19/7121951.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_7121951
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_formula_moiety         'C10 H8 F3 N O'
_chemical_formula_sum            'C10 H8 F3 N O'
_chemical_formula_weight         215.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 107.525(6)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   5.6878(14)
_cell_length_b                   20.542(5)
_cell_length_c                   8.921(2)
_cell_measurement_reflns_used    1565
_cell_measurement_temperature    173
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      2.00
_cell_volume                     993.9(4)
_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    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0412
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11961
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         1.983
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             440.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/petroleum ether'
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1814
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0420P)²+0.5670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1170
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1474
_reflns_number_total             1814
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c8cc04964e2.cif
_cod_data_source_block           19a
_cod_depositor_comments
'Adding full bibliography for 7121950--7121954.cif.'
_cod_database_code               7121951
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+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 0.1117(2) 0.19361(7) 0.20576(15) 0.0516(4) Uani 1 1 d . .
F2 F 0.1751(3) 0.06469(7) 0.1896(2) 0.0703(5) Uani 1 1 d . .
F3 F 0.5524(3) 0.06829(7) 0.3478(2) 0.0724(5) Uani 1 1 d . .
O4 O 0.6881(3) 0.19434(7) 0.49917(18) 0.0484(4) Uani 1 1 d . .
N5 N 0.5102(3) 0.26684(8) 0.3034(2) 0.0341(4) Uani 1 1 d D .
H5 H 0.372(3) 0.2754(11) 0.2132(19) 0.050(7) Uiso 1 1 d D .
C1 C 0.3038(4) 0.16704(11) 0.3214(2) 0.0384(5) Uani 1 1 d . .
C2 C 0.3292(4) 0.09560(12) 0.3139(3) 0.0497(6) Uani 1 1 d . .
C3 C 0.2326(5) 0.12094(12) 0.4352(3) 0.0546(7) Uani 1 1 d . .
H3A H 0.340998 0.119497 0.545284 0.065 Uiso 1 1 calc R U
H3B H 0.054983 0.114637 0.422066 0.065 Uiso 1 1 calc R U
C4 C 0.5213(4) 0.21108(10) 0.3827(2) 0.0342(5) Uani 1 1 d . .
C6 C 0.6830(4) 0.31890(9) 0.3405(2) 0.0320(5) Uani 1 1 d . .
C7 C 0.9309(4) 0.30976(11) 0.4210(3) 0.0391(5) Uani 1 1 d . .
H7 H 0.991584 0.267605 0.456235 0.047 Uiso 1 1 calc R U
C8 C 1.0888(4) 0.36283(11) 0.4494(3) 0.0449(6) Uani 1 1 d . .
H8 H 1.258181 0.356842 0.505262 0.054 Uiso 1 1 calc R U
C9 C 1.0034(4) 0.42422(11) 0.3978(3) 0.0448(6) Uani 1 1 d . .
H9 H 1.113529 0.460160 0.416780 0.054 Uiso 1 1 calc R U
C10 C 0.7561(4) 0.43303(11) 0.3182(3) 0.0432(5) Uani 1 1 d . .
H10 H 0.695883 0.475251 0.283167 0.052 Uiso 1 1 calc R U
C11 C 0.5968(4) 0.38080(10) 0.2895(2) 0.0383(5) Uani 1 1 d . .
H11 H 0.427218 0.387142 0.234624 0.046 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)
;
N N 0.0061 0.0033
;
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)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4 N5 C6 126.99(17)
C4 N5 H5 119.8(14)
C6 N5 H5 113.1(14)
F1 C1 C2 115.34(18)
F1 C1 C4 114.74(18)
C2 C1 C4 122.36(19)
F1 C1 C3 115.84(18)
C2 C1 C3 57.63(16)
C4 C1 C3 119.09(18)
F3 C2 F2 109.1(2)
F3 C2 C3 121.9(2)
F2 C2 C3 119.0(2)
F3 C2 C1 120.38(19)
F2 C2 C1 117.2(2)
C3 C2 C1 62.97(16)
C2 C3 C1 59.40(16)
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 126.10(19)
O4 C4 C1 118.93(19)
N5 C4 C1 114.97(17)
C11 C6 C7 119.74(19)
C11 C6 N5 117.47(18)
C7 C6 N5 122.77(18)
C8 C7 C6 119.3(2)
C8 C7 H7 120.4
C6 C7 H7 120.4
C9 C8 C7 120.9(2)
C9 C8 H8 119.5
C7 C8 H8 119.5
C8 C9 C10 119.5(2)
C8 C9 H9 120.3
C10 C9 H9 120.3
C11 C10 C9 120.2(2)
C11 C10 H10 119.9
C9 C10 H10 119.9
C10 C11 C6 120.3(2)
C10 C11 H11 119.8
C6 C11 H11 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C1 1.370(2)
F2 C2 1.347(3)
F3 C2 1.336(3)
O4 C4 1.227(2)
N5 C4 1.338(3)
N5 C6 1.422(3)
N5 H5 0.957(10)
C1 C2 1.478(3)
C1 C4 1.497(3)
C1 C3 1.530(3)
C2 C3 1.450(4)
C3 H3A 0.9900
C3 H3B 0.9900
C6 C11 1.389(3)
C6 C7 1.389(3)
C7 C8 1.386(3)
C7 H7 0.9500
C8 C9 1.380(3)
C8 H8 0.9500
C9 C10 1.384(3)
C9 H9 0.9500
C10 C11 1.378(3)
C10 H10 0.9500
C11 H11 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 O4 0.957(10) 1.981(13) 2.892(2) 158(2) 4_565 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 141.4(2)
C4 C1 C2 F3 -6.6(3)
C3 C1 C2 F3 -112.9(3)
F1 C1 C2 F2 4.8(3)
C4 C1 C2 F2 -143.3(2)
C3 C1 C2 F2 110.5(2)
F1 C1 C2 C3 -105.7(2)
C4 C1 C2 C3 106.2(2)
F3 C2 C3 C1 110.5(2)
F2 C2 C3 C1 -107.7(2)
F1 C1 C3 C2 104.8(2)
C4 C1 C3 C2 -111.9(2)
C6 N5 C4 O4 -2.5(3)
C6 N5 C4 C1 176.26(18)
F1 C1 C4 O4 171.04(19)
C2 C1 C4 O4 -40.7(3)
C3 C1 C4 O4 27.4(3)
F1 C1 C4 N5 -7.8(3)
C2 C1 C4 N5 140.4(2)
C3 C1 C4 N5 -151.5(2)
C4 N5 C6 C11 -153.7(2)
C4 N5 C6 C7 27.8(3)
C11 C6 C7 C8 0.1(3)
N5 C6 C7 C8 178.51(19)
C6 C7 C8 C9 -0.5(3)
C7 C8 C9 C10 0.8(3)
C8 C9 C10 C11 -0.6(3)
C9 C10 C11 C6 0.1(3)
C7 C6 C11 C10 0.1(3)
N5 C6 C11 C10 -178.38(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139188875
