#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/49/4034957.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_4034957
loop_
_publ_author_name
'Wang, Quande'
'Tsui, Gavin Chit'
_publ_section_title
;
 Copper-Mediated Domino Cyclization/Trifluoromethylation of Propargylic
 N-Hydroxylamines: Synthesis of 4-Trifluoromethyl-4-isoxazolines.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2971
_journal_page_last               2979
_journal_paper_doi               10.1021/acs.joc.7b03191
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C25 H22 F3 N O4 S'
_chemical_formula_weight         489.49
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 110.798(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1119(17)
_cell_length_b                   9.9385(11)
_cell_length_c                   17.9114(19)
_cell_measurement_reflns_used    779
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     2348.4(5)
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_collection       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            50104
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         2.566
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5983
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0782P)²+0.6616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1432
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3603
_reflns_number_total             4210
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b03191_si_001.cif
_cod_data_source_block           WQD694
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034957
_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_min   0.909
_shelx_estimated_absorpt_t_max   0.944
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
N1 N 0.30606(12) 1.14902(17) 0.09365(10) 0.0548(4) Uani 1 1 d . .
S1 S 0.38907(4) 1.11773(6) 0.18723(3) 0.0622(2) Uani 1 1 d . .
F1 F 0.24982(18) 0.88571(17) -0.12877(9) 0.1096(6) Uani 1 1 d . .
F2 F 0.29716(14) 0.75497(14) -0.02956(10) 0.0943(5) Uani 1 1 d . .
F3 F 0.40069(16) 0.8962(2) -0.04603(15) 0.1295(8) Uani 1 1 d . .
O1 O 0.47806(12) 1.18781(17) 0.18823(11) 0.0786(5) Uani 1 1 d . .
O2 O 0.33745(14) 1.1559(2) 0.23892(10) 0.0877(6) Uani 1 1 d . .
O3 O 0.21321(10) 1.07660(15) 0.08354(8) 0.0559(4) Uani 1 1 d . .
O4 O -0.10927(14) 0.6129(2) 0.00578(12) 0.0885(5) Uani 1 1 d . .
C1 C 0.4671(3) 0.5203(3) 0.2133(2) 0.1142(11) Uani 1 1 d . .
H1B H 0.5251 0.5000 0.1992 0.171 Uiso 1 1 calc R U
H1C H 0.4796 0.4916 0.2672 0.171 Uiso 1 1 calc R U
H1D H 0.4089 0.4740 0.1777 0.171 Uiso 1 1 calc R U
C2 C 0.44796(19) 0.6700(2) 0.20687(15) 0.0721(6) Uani 1 1 d . .
C3 C 0.36865(19) 0.7243(3) 0.22416(15) 0.0773(7) Uani 1 1 d . .
H3A H 0.3261 0.6676 0.2392 0.093 Uiso 1 1 calc R U
C4 C 0.35076(17) 0.8602(3) 0.21979(13) 0.0679(6) Uani 1 1 d . .
H4A H 0.2971 0.8952 0.2323 0.082 Uiso 1 1 calc R U
C5 C 0.41302(15) 0.9449(2) 0.19664(11) 0.0555(5) Uani 1 1 d . .
C6 C 0.49292(17) 0.8926(2) 0.17807(14) 0.0655(6) Uani 1 1 d . .
H6A H 0.5346 0.9491 0.1620 0.079 Uiso 1 1 calc R U
C7 C 0.50959(19) 0.7568(3) 0.18374(16) 0.0751(7) Uani 1 1 d . .
H7A H 0.5636 0.7216 0.1718 0.090 Uiso 1 1 calc R U
C8 C 0.33879(15) 1.1076(2) 0.02638(11) 0.0529(5) Uani 1 1 d . .
H8A H 0.4113 1.0860 0.0471 0.063 Uiso 1 1 calc R U
C9 C 0.31934(14) 1.2219(2) -0.03348(11) 0.0513(4) Uani 1 1 d . .
C10 C 0.38014(16) 1.3345(2) -0.01335(13) 0.0627(5) Uani 1 1 d . .
H10A H 0.4342 1.3368 0.0351 0.075 Uiso 1 1 calc R U
C11 C 0.36218(18) 1.4434(2) -0.06373(14) 0.0669(6) Uani 1 1 d . .
H11A H 0.4031 1.5193 -0.0480 0.080 Uiso 1 1 calc R U
C12 C 0.28466(17) 1.4426(2) -0.13720(12) 0.0599(5) Uani 1 1 d . .
C13 C 0.22469(17) 1.3293(2) -0.15752(13) 0.0662(6) Uani 1 1 d . .
H13A H 0.1721 1.3261 -0.2068 0.079 Uiso 1 1 calc R U
C14 C 0.24073(16) 1.2206(2) -0.10660(13) 0.0615(5) Uani 1 1 d . .
H14A H 0.1984 1.1459 -0.1215 0.074 Uiso 1 1 calc R U
C15 C 0.2663(2) 1.5616(3) -0.19256(16) 0.0854(8) Uani 1 1 d . .
H15A H 0.3154 1.6304 -0.1683 0.128 Uiso 1 1 calc R U
H15B H 0.2725 1.5342 -0.2420 0.128 Uiso 1 1 calc R U
H15C H 0.1994 1.5963 -0.2027 0.128 Uiso 1 1 calc R U
C16 C 0.27857(16) 0.9810(2) -0.00132(12) 0.0548(5) Uani 1 1 d . .
C17 C 0.3062(2) 0.8801(2) -0.05035(15) 0.0698(6) Uani 1 1 d . .
C18 C 0.20650(15) 0.9727(2) 0.03052(11) 0.0523(5) Uani 1 1 d . .
C19 C 0.12219(15) 0.8811(2) 0.02161(12) 0.0560(5) Uani 1 1 d . .
C20 C 0.08864(17) 0.8579(3) 0.08435(13) 0.0654(6) Uani 1 1 d . .
H20A H 0.1191 0.9034 0.1323 0.078 Uiso 1 1 calc R U
C21 C 0.01111(18) 0.7688(3) 0.07713(14) 0.0714(6) Uani 1 1 d . .
H21A H -0.0100 0.7541 0.1201 0.086 Uiso 1 1 calc R U
C22 C -0.03513(16) 0.7015(2) 0.00633(14) 0.0652(6) Uani 1 1 d . .
C23 C -0.00514(18) 0.7250(3) -0.05727(14) 0.0720(6) Uani 1 1 d . .
H23A H -0.0373 0.6810 -0.1055 0.086 Uiso 1 1 calc R U
C24 C 0.07316(18) 0.8145(3) -0.04982(13) 0.0683(6) Uani 1 1 d . .
H24A H 0.0931 0.8300 -0.0933 0.082 Uiso 1 1 calc R U
C25 C -0.1658(2) 0.5476(3) -0.0665(2) 0.0955(9) Uani 1 1 d . .
H25A H -0.2147 0.4888 -0.0577 0.143 Uiso 1 1 calc R U
H25B H -0.2000 0.6137 -0.1060 0.143 Uiso 1 1 calc R U
H25C H -0.1208 0.4961 -0.0850 0.143 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 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'
S S 0.1246 0.1234 '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
O3 N1 C8 106.69(14)
O3 N1 S1 107.98(12)
C8 N1 S1 116.31(12)
O2 S1 O1 120.91(12)
O2 S1 N1 105.13(9)
O1 S1 N1 102.60(10)
O2 S1 C5 109.07(12)
O1 S1 C5 109.79(10)
N1 S1 C5 108.49(9)
C18 O3 N1 107.16(13)
C22 O4 C25 118.9(2)
C3 C2 C7 118.1(2)
C3 C2 C1 120.6(3)
C7 C2 C1 121.4(3)
C4 C3 C2 121.5(2)
C3 C4 C5 119.5(2)
C4 C5 C6 120.2(2)
C4 C5 S1 120.36(17)
C6 C5 S1 119.44(17)
C7 C6 C5 119.0(2)
C6 C7 C2 121.7(2)
N1 C8 C16 101.35(16)
N1 C8 C9 109.46(15)
C16 C8 C9 117.05(17)
C10 C9 C14 118.08(19)
C10 C9 C8 118.90(17)
C14 C9 C8 122.97(19)
C11 C10 C9 121.04(19)
C10 C11 C12 121.3(2)
C13 C12 C11 117.5(2)
C13 C12 C15 121.5(2)
C11 C12 C15 121.0(2)
C12 C13 C14 121.6(2)
C13 C14 C9 120.4(2)
C18 C16 C17 128.0(2)
C18 C16 C8 109.79(17)
C17 C16 C8 121.95(19)
F2 C17 F3 107.2(2)
F2 C17 F1 104.7(2)
F3 C17 F1 105.4(2)
F2 C17 C16 113.69(19)
F3 C17 C16 111.0(2)
F1 C17 C16 114.2(2)
C16 C18 O3 111.78(18)
C16 C18 C19 134.96(19)
O3 C18 C19 113.26(17)
C20 C19 C24 117.8(2)
C20 C19 C18 120.98(19)
C24 C19 C18 121.21(19)
C21 C20 C19 121.3(2)
C22 C21 C20 120.0(2)
O4 C22 C23 124.5(2)
O4 C22 C21 115.6(2)
C23 C22 C21 119.9(2)
C22 C23 C24 120.0(2)
C23 C24 C19 120.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O3 1.449(2)
N1 C8 1.493(2)
N1 S1 1.6982(17)
S1 O2 1.4181(17)
S1 O1 1.4304(18)
S1 C5 1.748(2)
F1 C17 1.347(3)
F2 C17 1.317(3)
F3 C17 1.318(3)
O3 C18 1.383(2)
O4 C22 1.365(3)
O4 C25 1.415(3)
C1 C2 1.510(4)
C2 C3 1.373(4)
C2 C7 1.388(4)
C3 C4 1.371(4)
C4 C5 1.382(3)
C5 C6 1.385(3)
C6 C7 1.368(3)
C8 C16 1.501(3)
C8 C9 1.519(3)
C9 C10 1.378(3)
C9 C14 1.384(3)
C10 C11 1.374(3)
C11 C12 1.381(3)
C12 C13 1.377(3)
C12 C15 1.506(3)
C13 C14 1.380(3)
C16 C18 1.334(3)
C16 C17 1.474(3)
C18 C19 1.461(3)
C19 C20 1.385(3)
C19 C24 1.387(3)
C20 C21 1.377(3)
C21 C22 1.376(3)
C22 C23 1.369(3)
C23 C24 1.387(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328784
