#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/89/7108911.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_7108911
loop_
_publ_author_name
'Yusuke Yasu'
'Takashi Koike'
'Munetaka Akita'
_publ_section_title
;
 Visible-light-induced synthesis of a variety of trifluoromethylated
 alkenes from potassium vinyltrifluoroborates by photoredox catalysis
;
_journal_issue                   20
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2037
_journal_page_last               2039
_journal_paper_doi               10.1039/c3cc39235j
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C10 H8 F3 N O2'
_chemical_formula_weight         231.17
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.452(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   13.040(2)
_cell_length_b                   12.456(2)
_cell_length_c                   19.177(4)
_cell_measurement_reflns_used    3857
_cell_measurement_temperature    93
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.19
_cell_volume                     3016.3(9)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.901
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17047
_diffrn_reflns_theta_full        28.76
_diffrn_reflns_theta_max         28.76
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.9652
_exptl_absorpt_correction_T_min  0.9451
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platet
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         7077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0745P)²+0.2500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1546
_reflns_number_gt                4371
_reflns_number_total             7077
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc39235j.txt
_cod_data_source_block           vitamineb3_cf3_alkene1_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        3016.4(10)
_cod_original_sg_symbol_H-M      'P2(1)/c '
_cod_database_code               7108911
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 1.05914(16) 0.93123(14) 0.43898(9) 0.0269(4) Uani 1 1 d .
C2 C 0.93425(17) 0.78622(17) 0.40154(10) 0.0212(5) Uani 1 1 d .
C3 C 1.01782(16) 0.71324(16) 0.41002(10) 0.0192(4) Uani 1 1 d .
H3 H 1.0042 0.6392 0.4000 0.023 Uiso 1 1 calc R
C1 C 0.95995(18) 0.89418(17) 0.41681(10) 0.0241(5) Uani 1 1 d .
H1 H 0.9035 0.9443 0.4111 0.029 Uiso 1 1 calc R
C4 C 1.12059(17) 0.75042(17) 0.43313(10) 0.0205(4) Uani 1 1 d .
C5 C 1.13762(19) 0.85966(18) 0.44681(11) 0.0248(5) Uani 1 1 d .
H5 H 1.2085 0.8845 0.4625 0.030 Uiso 1 1 calc R
O2 O 1.30320(12) 0.71954(13) 0.47126(8) 0.0314(4) Uani 1 1 d .
C6 C 1.20975(17) 0.67290(18) 0.44300(10) 0.0224(5) Uani 1 1 d .
O1 O 1.19934(12) 0.57900(12) 0.42784(9) 0.0307(4) Uani 1 1 d .
C7 C 1.39327(19) 0.6481(2) 0.48515(15) 0.0464(7) Uani 1 1 d .
H7A H 1.3818 0.5892 0.5163 0.070 Uiso 1 1 calc R
H7B H 1.4573 0.6878 0.5091 0.070 Uiso 1 1 calc R
H7C H 1.4018 0.6187 0.4395 0.070 Uiso 1 1 calc R
C8 C 0.82216(17) 0.75648(17) 0.37883(10) 0.0233(5) Uani 1 1 d .
H8 H 0.7718 0.8129 0.3668 0.028 Uiso 1 1 calc R
C9 C 0.78584(17) 0.65651(18) 0.37390(11) 0.0255(5) Uani 1 1 d .
H9 H 0.8356 0.5993 0.3835 0.031 Uiso 1 1 calc R
C10 C 0.6695(2) 0.6293(2) 0.35377(12) 0.0316(6) Uani 1 1 d .
F1 F 0.60865(11) 0.71603(12) 0.33965(8) 0.0474(4) Uani 1 1 d .
F2 F 0.64251(12) 0.57822(13) 0.40751(9) 0.0522(4) Uani 1 1 d .
F3 F 0.64437(12) 0.56697(14) 0.29673(9) 0.0570(5) Uani 1 1 d .
N2 N -0.05738(14) 0.59562(14) 0.23820(9) 0.0229(4) Uani 1 1 d .
C14 C -0.13597(17) 0.41952(16) 0.22422(10) 0.0194(4) Uani 1 1 d .
C12 C 0.05267(16) 0.43702(17) 0.26018(10) 0.0192(4) Uani 1 1 d .
C11 C 0.03735(17) 0.54846(17) 0.25647(10) 0.0210(5) Uani 1 1 d .
H11 H 0.0983 0.5932 0.2677 0.025 Uiso 1 1 calc R
C13 C -0.03680(16) 0.37229(17) 0.24374(10) 0.0197(4) Uani 1 1 d .
H13 H -0.0300 0.2964 0.2459 0.024 Uiso 1 1 calc R
C15 C -0.14247(18) 0.53119(17) 0.22236(10) 0.0227(5) Uani 1 1 d .
H15 H -0.2107 0.5633 0.2092 0.027 Uiso 1 1 calc R
O4 O -0.32025(12) 0.40797(12) 0.18655(8) 0.0308(4) Uani 1 1 d .
C16 C -0.23142(17) 0.34989(17) 0.20617(10) 0.0209(4) Uani 1 1 d .
O3 O -0.22965(12) 0.25291(12) 0.20864(8) 0.0277(4) Uani 1 1 d .
C17 C -0.41798(18) 0.3482(2) 0.16927(14) 0.0376(6) Uani 1 1 d .
H17A H -0.4183 0.2991 0.1293 0.056 Uiso 1 1 calc R
H17B H -0.4778 0.3980 0.1553 0.056 Uiso 1 1 calc R
H17C H -0.4243 0.3069 0.2115 0.056 Uiso 1 1 calc R
C18 C 0.15808(17) 0.38734(18) 0.28045(10) 0.0236(5) Uani 1 1 d .
H18 H 0.1610 0.3111 0.2819 0.028 Uiso 1 1 calc R
C19 C 0.24908(18) 0.43930(19) 0.29686(12) 0.0283(5) Uani 1 1 d .
H19 H 0.2484 0.5155 0.2953 0.034 Uiso 1 1 calc R
C20 C 0.3520(2) 0.3833(2) 0.31756(14) 0.0384(6) Uani 1 1 d .
F4 F 0.34448(12) 0.27637(12) 0.31689(9) 0.0518(4) Uani 1 1 d .
F6 F 0.41397(13) 0.40719(14) 0.27338(11) 0.0646(5) Uani 1 1 d .
F5 F 0.40707(13) 0.40961(15) 0.38379(9) 0.0679(6) Uani 1 1 d .
O5 O 0.78836(12) 0.07987(12) 0.35329(9) 0.0318(4) Uani 1 1 d .
O6 O 0.68257(12) 0.22100(13) 0.35593(8) 0.0309(4) Uani 1 1 d .
N3 N 0.92687(16) 0.43171(14) 0.41670(9) 0.0268(4) Uani 1 1 d .
C22 C 1.05240(17) 0.28610(17) 0.42552(10) 0.0208(5) Uani 1 1 d .
C23 C 0.96947(16) 0.21347(17) 0.40294(10) 0.0207(5) Uani 1 1 d .
H23 H 0.9835 0.1393 0.3982 0.025 Uiso 1 1 calc R
C25 C 0.84868(19) 0.36021(17) 0.39501(11) 0.0247(5) Uani 1 1 d .
H25 H 0.7777 0.3853 0.3842 0.030 Uiso 1 1 calc R
C24 C 0.86603(17) 0.25111(17) 0.38746(10) 0.0210(5) Uani 1 1 d .
C21 C 1.02592(19) 0.39407(17) 0.43146(10) 0.0246(5) Uani 1 1 d .
H21 H 1.0821 0.4439 0.4470 0.029 Uiso 1 1 calc R
C26 C 0.77729(17) 0.17377(18) 0.36392(11) 0.0239(5) Uani 1 1 d .
C27 C 0.59245(19) 0.1501(2) 0.33533(16) 0.0445(7) Uani 1 1 d .
H27A H 0.5922 0.1157 0.2893 0.067 Uiso 1 1 calc R
H27B H 0.5271 0.1916 0.3302 0.067 Uiso 1 1 calc R
H27C H 0.5969 0.0950 0.3724 0.067 Uiso 1 1 calc R
C28 C 1.16461(17) 0.25615(17) 0.44516(10) 0.0229(5) Uani 1 1 d .
H28 H 1.2150 0.3128 0.4537 0.028 Uiso 1 1 calc R
C29 C 1.20161(17) 0.15676(18) 0.45199(11) 0.0242(5) Uani 1 1 d .
H29 H 1.1524 0.0992 0.4411 0.029 Uiso 1 1 calc R
C30 C 1.3184(2) 0.13001(19) 0.47627(11) 0.0320(6) Uani 1 1 d .
F9 F 1.37734(11) 0.21732(13) 0.49246(9) 0.0497(4) Uani 1 1 d .
F7 F 1.35122(12) 0.07716(15) 0.42714(9) 0.0587(5) Uani 1 1 d .
F8 F 1.33660(12) 0.07014(13) 0.53545(9) 0.0536(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 0.0033 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'
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'
F F 0.0171 0.0103 '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
C5 N1 C1 117.23(19)
C3 C2 C1 117.5(2)
C3 C2 C8 124.16(19)
C1 C2 C8 118.3(2)
C4 C3 C2 119.01(19)
C4 C3 H3 120.5
C2 C3 H3 120.5
N1 C1 C2 124.0(2)
N1 C1 H1 118.0
C2 C1 H1 118.0
C3 C4 C5 118.9(2)
C3 C4 C6 119.22(18)
C5 C4 C6 121.8(2)
N1 C5 C4 123.3(2)
N1 C5 H5 118.4
C4 C5 H5 118.4
C6 O2 C7 115.07(19)
O1 C6 O2 123.8(2)
O1 C6 C4 124.22(19)
O2 C6 C4 111.98(18)
O2 C7 H7A 109.5
O2 C7 H7B 109.5
H7A C7 H7B 109.5
O2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C9 C8 C2 124.8(2)
C9 C8 H8 117.6
C2 C8 H8 117.6
C8 C9 C10 123.2(2)
C8 C9 H9 118.4
C10 C9 H9 118.4
F3 C10 F1 107.4(2)
F3 C10 F2 107.6(2)
F1 C10 F2 106.64(19)
F3 C10 C9 111.84(19)
F1 C10 C9 112.4(2)
F2 C10 C9 110.68(18)
C11 N2 C15 117.11(18)
C13 C14 C15 118.54(19)
C13 C14 C16 119.13(19)
C15 C14 C16 122.33(19)
C13 C12 C11 117.55(19)
C13 C12 C18 119.56(19)
C11 C12 C18 122.88(19)
N2 C11 C12 124.1(2)
N2 C11 H11 117.9
C12 C11 H11 117.9
C14 C13 C12 119.34(19)
C14 C13 H13 120.3
C12 C13 H13 120.3
N2 C15 C14 123.4(2)
N2 C15 H15 118.3
C14 C15 H15 118.3
C16 O4 C17 116.07(18)
O3 C16 O4 123.9(2)
O3 C16 C14 124.6(2)
O4 C16 C14 111.48(18)
O4 C17 H17A 109.5
O4 C17 H17B 109.5
H17A C17 H17B 109.5
O4 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C19 C18 C12 125.7(2)
C19 C18 H18 117.2
C12 C18 H18 117.2
C18 C19 C20 122.4(2)
C18 C19 H19 118.8
C20 C19 H19 118.8
F5 C20 F4 105.9(2)
F5 C20 F6 106.3(2)
F4 C20 F6 105.6(2)
F5 C20 C19 112.2(2)
F4 C20 C19 114.1(2)
F6 C20 C19 112.1(2)
C26 O6 C27 115.23(19)
C21 N3 C25 116.93(19)
C23 C22 C21 117.4(2)
C23 C22 C28 124.21(19)
C21 C22 C28 118.32(19)
C24 C23 C22 118.97(19)
C24 C23 H23 120.5
C22 C23 H23 120.5
N3 C25 C24 123.4(2)
N3 C25 H25 118.3
C24 C25 H25 118.3
C23 C24 C25 118.8(2)
C23 C24 C26 119.15(19)
C25 C24 C26 122.0(2)
N3 C21 C22 124.4(2)
N3 C21 H21 117.8
C22 C21 H21 117.8
O5 C26 O6 123.6(2)
O5 C26 C24 124.4(2)
O6 C26 C24 112.03(19)
O6 C27 H27A 109.5
O6 C27 H27B 109.5
H27A C27 H27B 109.5
O6 C27 H27C 109.5
H27A C27 H27C 109.5
H27B C27 H27C 109.5
C29 C28 C22 125.4(2)
C29 C28 H28 117.3
C22 C28 H28 117.3
C28 C29 C30 123.4(2)
C28 C29 H29 118.3
C30 C29 H29 118.3
F7 C30 F9 107.9(2)
F7 C30 F8 108.2(2)
F9 C30 F8 106.93(18)
F7 C30 C29 112.01(18)
F9 C30 C29 111.8(2)
F8 C30 C29 109.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.337(3)
N1 C1 1.339(3)
C2 C3 1.397(3)
C2 C1 1.399(3)
C2 C8 1.465(3)
C3 C4 1.382(3)
C3 H3 0.9500
C1 H1 0.9500
C4 C5 1.393(3)
C4 C6 1.487(3)
C5 H5 0.9500
O2 C6 1.337(2)
O2 C7 1.445(3)
C6 O1 1.205(2)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 C9 1.327(3)
C8 H8 0.9500
C9 C10 1.507(3)
C9 H9 0.9500
C10 F3 1.315(3)
C10 F1 1.328(3)
C10 F2 1.331(3)
N2 C11 1.333(3)
N2 C15 1.341(3)
C14 C13 1.385(3)
C14 C15 1.394(3)
C14 C16 1.485(3)
C12 C13 1.388(3)
C12 C11 1.402(3)
C12 C18 1.469(3)
C11 H11 0.9500
C13 H13 0.9500
C15 H15 0.9500
O4 C16 1.338(3)
O4 C17 1.441(3)
C16 O3 1.209(2)
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 C19 1.319(3)
C18 H18 0.9500
C19 C20 1.476(3)
C19 H19 0.9500
C20 F5 1.335(3)
C20 F4 1.336(3)
C20 F6 1.342(3)
O5 C26 1.202(3)
O6 C26 1.342(3)
O6 C27 1.444(3)
N3 C21 1.336(3)
N3 C25 1.339(3)
C22 C23 1.394(3)
C22 C21 1.400(3)
C22 C28 1.465(3)
C23 C24 1.388(3)
C23 H23 0.9500
C25 C24 1.391(3)
C25 H25 0.9500
C24 C26 1.487(3)
C21 H21 0.9500
C27 H27A 0.9800
C27 H27B 0.9800
C27 H27C 0.9800
C28 C29 1.323(3)
C28 H28 0.9500
C29 C30 1.514(3)
C29 H29 0.9500
C30 F7 1.306(3)
C30 F9 1.323(3)
C30 F8 1.329(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139183019
