#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/47/4034777.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_4034777
loop_
_publ_author_name
'Wang, Xue-Juan'
'Su, Yan'
'Li, Rui'
'Gu, Peiming'
_publ_section_title
;
 Tf₂O-Promoted Intramolecular Schmidt Reaction of the ω-Azido
 Carboxylic Acids.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5816
_journal_page_last               5824
_journal_paper_doi               10.1021/acs.joc.8b00475
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C11 H12 F3 N O2 S'
_chemical_formula_sum            'C11 H12 F3 N O2 S'
_chemical_formula_weight         279.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.8054(8)
_cell_length_b                   7.8126(6)
_cell_length_c                   28.528(3)
_cell_measurement_reflns_used    1813
_cell_measurement_temperature    298.84(10)
_cell_measurement_theta_max      26.8560
_cell_measurement_theta_min      3.7540
_cell_volume                     2408.3(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.84(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -27.00   44.05   1.4500    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000 -150.0000 49

#__ type_ start__ end____ width___ exp.time_
  2 omega   17.00   67.75   1.4500    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega  -24.00   84.75   1.4500    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000 -120.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0284427000
_diffrn_orient_matrix_UB_12      0.0375178000
_diffrn_orient_matrix_UB_13      0.0199063000
_diffrn_orient_matrix_UB_21      0.0224786000
_diffrn_orient_matrix_UB_22      -0.0677440000
_diffrn_orient_matrix_UB_23      0.0142036000
_diffrn_orient_matrix_UB_31      0.0547324000
_diffrn_orient_matrix_UB_32      0.0473549000
_diffrn_orient_matrix_UB_33      0.0045097000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            8664
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.296
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2359
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1499
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1819
_reflns_number_total             2359
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b00475_si_002.cif
_cod_data_source_block           wxj_02016
_cod_database_code               4034777
_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.
;
_reflns_odcompleteness_completeness 98.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-07-15
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
S1 S 0.51511(5) 0.20475(8) 0.59210(2) 0.0235(2) Uani 1 1 d .
F1 F 0.49380(16) 0.2982(3) 0.50442(7) 0.0602(6) Uani 1 1 d .
F2 F 0.61482(16) 0.0862(3) 0.51521(7) 0.0605(6) Uani 1 1 d .
F3 F 0.67393(17) 0.3390(3) 0.53352(6) 0.0656(6) Uani 1 1 d .
O1 O 0.61340(15) 0.1207(2) 0.61616(7) 0.0368(5) Uani 1 1 d .
O2 O 0.39789(15) 0.1261(2) 0.58503(7) 0.0360(5) Uani 1 1 d .
N1 N 0.49616(15) 0.3904(3) 0.61264(7) 0.0235(5) Uani 1 1 d .
C1 C 0.51562(19) 0.4105(3) 0.71291(9) 0.0253(6) Uani 1 1 d .
H1 H 0.4490 0.3562 0.6986 0.030 Uiso 1 1 calc R
C2 C 0.5233(2) 0.4135(4) 0.76116(9) 0.0309(6) Uani 1 1 d .
H2 H 0.4620 0.3613 0.7791 0.037 Uiso 1 1 calc R
C3 C 0.6219(2) 0.4943(3) 0.78311(9) 0.0290(6) Uani 1 1 d .
H3 H 0.6268 0.4979 0.8156 0.035 Uiso 1 1 calc R
C4 C 0.7128(2) 0.5691(3) 0.75587(9) 0.0303(6) Uani 1 1 d .
H4 H 0.7801 0.6219 0.7702 0.036 Uiso 1 1 calc R
C5 C 0.7044(2) 0.5661(3) 0.70778(8) 0.0255(6) Uani 1 1 d .
H5 H 0.7659 0.6179 0.6899 0.031 Uiso 1 1 calc R
C6 C 0.60549(18) 0.4868(3) 0.68546(8) 0.0200(5) Uani 1 1 d .
C7 C 0.59908(19) 0.4953(3) 0.63240(8) 0.0228(5) Uani 1 1 d .
H7 H 0.6782 0.4592 0.6188 0.027 Uiso 1 1 calc R
C8 C 0.5645(2) 0.6732(3) 0.61444(9) 0.0313(6) Uani 1 1 d .
H8A H 0.5993 0.7617 0.6343 0.038 Uiso 1 1 calc R
H8B H 0.5935 0.6900 0.5826 0.038 Uiso 1 1 calc R
C9 C 0.4242(2) 0.6744(3) 0.61655(10) 0.0345(6) Uani 1 1 d .
H9A H 0.3905 0.7617 0.5960 0.041 Uiso 1 1 calc R
H9B H 0.3957 0.6956 0.6483 0.041 Uiso 1 1 calc R
C10 C 0.3859(2) 0.4965(4) 0.60021(10) 0.0323(6) Uani 1 1 d .
H10A H 0.3125 0.4573 0.6166 0.039 Uiso 1 1 calc R
H10B H 0.3704 0.4945 0.5667 0.039 Uiso 1 1 calc R
C11 C 0.5782(3) 0.2327(4) 0.53299(9) 0.0384(7) 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'
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'
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
O1 S1 N1 109.98(10)
O1 S1 C11 102.76(12)
O2 S1 O1 122.21(12)
O2 S1 N1 109.54(10)
O2 S1 C11 104.61(12)
N1 S1 C11 106.30(13)
C7 N1 S1 123.26(14)
C7 N1 C10 112.3(2)
C10 N1 S1 121.68(16)
C2 C1 H1 119.5
C2 C1 C6 121.0(2)
C6 C1 H1 119.5
C1 C2 H2 119.9
C1 C2 C3 120.3(2)
C3 C2 H2 119.9
C2 C3 H3 120.5
C4 C3 C2 119.0(2)
C4 C3 H3 120.5
C3 C4 H4 119.8
C5 C4 C3 120.5(2)
C5 C4 H4 119.8
C4 C5 H5 119.5
C4 C5 C6 121.0(2)
C6 C5 H5 119.5
C1 C6 C5 118.2(2)
C1 C6 C7 123.5(2)
C5 C6 C7 118.2(2)
N1 C7 C6 112.77(18)
N1 C7 H7 110.0
N1 C7 C8 101.00(18)
C6 C7 H7 110.0
C6 C7 C8 112.7(2)
C8 C7 H7 110.0
C7 C8 H8A 111.0
C7 C8 H8B 111.0
H8A C8 H8B 109.0
C9 C8 C7 103.69(19)
C9 C8 H8A 111.0
C9 C8 H8B 111.0
C8 C9 H9A 110.8
C8 C9 H9B 110.8
C8 C9 C10 104.7(2)
H9A C9 H9B 108.9
C10 C9 H9A 110.8
C10 C9 H9B 110.8
N1 C10 C9 102.52(19)
N1 C10 H10A 111.3
N1 C10 H10B 111.3
C9 C10 H10A 111.3
C9 C10 H10B 111.3
H10A C10 H10B 109.2
F1 C11 S1 110.84(19)
F1 C11 F3 107.5(3)
F2 C11 S1 111.4(2)
F2 C11 F1 107.8(2)
F2 C11 F3 108.4(2)
F3 C11 S1 110.74(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4249(17)
S1 O2 1.4222(17)
S1 N1 1.578(2)
S1 C11 1.832(3)
F1 C11 1.326(3)
F2 C11 1.312(3)
F3 C11 1.327(3)
N1 C7 1.492(3)
N1 C10 1.494(3)
C1 H1 0.9300
C1 C2 1.379(4)
C1 C6 1.383(3)
C2 H2 0.9300
C2 C3 1.388(3)
C3 H3 0.9300
C3 C4 1.382(3)
C4 H4 0.9300
C4 C5 1.375(3)
C5 H5 0.9300
C5 C6 1.389(3)
C6 C7 1.517(3)
C7 H7 0.9800
C7 C8 1.527(4)
C8 H8A 0.9700
C8 H8B 0.9700
C8 C9 1.518(4)
C9 H9A 0.9700
C9 H9B 0.9700
C9 C10 1.523(4)
C10 H10A 0.9700
C10 H10B 0.9700
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
S1 N1 C7 C6 -98.4(2)
S1 N1 C7 C8 141.13(19)
S1 N1 C10 C9 -165.28(18)
O1 S1 N1 C7 31.3(2)
O1 S1 N1 C10 -168.96(19)
O1 S1 C11 F1 175.1(2)
O1 S1 C11 F2 55.0(2)
O1 S1 C11 F3 -65.7(2)
O2 S1 N1 C7 168.20(18)
O2 S1 N1 C10 -32.0(2)
O2 S1 C11 F1 46.5(2)
O2 S1 C11 F2 -73.6(2)
O2 S1 C11 F3 165.8(2)
N1 S1 C11 F1 -69.4(2)
N1 S1 C11 F2 170.56(18)
N1 S1 C11 F3 49.9(2)
N1 C7 C8 C9 36.0(2)
C1 C2 C3 C4 -0.9(4)
C1 C6 C7 N1 -8.7(3)
C1 C6 C7 C8 104.9(3)
C2 C1 C6 C5 0.4(4)
C2 C1 C6 C7 -176.9(2)
C2 C3 C4 C5 1.1(4)
C3 C4 C5 C6 -0.6(4)
C4 C5 C6 C1 -0.1(4)
C4 C5 C6 C7 177.3(2)
C5 C6 C7 N1 174.1(2)
C5 C6 C7 C8 -72.4(3)
C6 C1 C2 C3 0.2(4)
C6 C7 C8 C9 -84.6(2)
C7 N1 C10 C9 -3.5(3)
C7 C8 C9 C10 -39.9(2)
C8 C9 C10 N1 26.4(3)
C10 N1 C7 C6 100.2(2)
C10 N1 C7 C8 -20.3(2)
C11 S1 N1 C7 -79.3(2)
C11 S1 N1 C10 80.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 86276449
