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#$Date: 2019-11-25 10:23:45 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240668 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/00/4130091.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_4130091
loop_
_publ_author_name
'Nagamani, Chikkannagari'
'Liu, Huiying'
'Moore, Jeffrey S.'
_publ_contact_author
; 
Jeffrey S. Moore 
University of Illinois 
Department of Chemistry 
Urbana, Illinois  61801 
USA  
;
_publ_section_title
;
 Mechanogeneration of Acid from Oxime Sulfonates.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2540
_journal_page_last               2543
_journal_paper_doi               10.1021/jacs.6b00097
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C10 H10 F3 N O3'
_chemical_formula_sum            'C10 H10 F3 N O3'
_chemical_formula_weight         249.19
_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   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
; 
? 
;
_cell_angle_alpha                90
_cell_angle_beta                 94.2965(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0912(3)
_cell_length_b                   8.9533(5)
_cell_length_c                   23.0489(12)
_cell_measurement_reflns_used    9839
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.35
_cell_measurement_theta_min      3.85
_cell_volume                     1047.69(10)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2014.9-0 (Bruker, 2014)'
_computing_data_reduction
; 
SAINT V8.34A, XPREP v2014/2, SADABS V2014/4, TWINABS V2012/1 
(Bruker, 2012 & 2014) 
;
_computing_molecular_graphics
; 
SHELXTL v2014-4 (Bruker, 2014), CrystalMaker v2.7.7 (CrystalMaker, 1994) 
;
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'
_computing_structure_refinement  'SHELX-2014-6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELX-2014-4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker D8 Venture/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_wavelength_id  cd48vsa
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.346
_diffrn_reflns_theta_min         3.846
_exptl_absorpt_coefficient_mu    1.330
_exptl_absorpt_correction_T_max  0.98669
_exptl_absorpt_correction_T_min  0.71896
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_id                cd48vsa
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (1 -2 -1) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.502
_exptl_crystal_size_mid          0.455
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.0090(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         1921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0106P)²+2.8247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1237
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1801
_reflns_number_total             1921
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b00097_si_002.cif
_cod_data_source_block           cd48vsa
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4130091
_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   0.555
_shelx_estimated_absorpt_t_max   0.984
_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
F1 F 0.6063(4) 0.45942(19) 0.12819(8) 0.0312(5) Uani 1 1 d . .
F2 F 0.9603(4) 0.5833(2) 0.11748(8) 0.0347(5) Uani 1 1 d . .
F3 F 0.6539(4) 0.5732(2) 0.04803(7) 0.0338(5) Uani 1 1 d . .
N1 N 0.5241(5) 0.8216(3) 0.09035(10) 0.0204(5) Uani 1 1 d . .
O1 O 0.4208(4) 0.9521(2) 0.11096(9) 0.0218(5) Uani 1 1 d . .
H1 H 0.399(7) 1.003(4) 0.0754(16) 0.033 Uiso 1 1 d . U
O2 O 0.3872(4) 0.7378(2) 0.36889(8) 0.0197(5) Uani 1 1 d . .
O3 O 0.2250(4) 0.6318(2) 0.47724(9) 0.0239(5) Uani 1 1 d . .
H3 H 0.168(8) 0.654(5) 0.5062(17) 0.036 Uiso 1 1 d . U
C1 C 0.5269(5) 0.7261(3) 0.19326(12) 0.0167(6) Uani 1 1 d . .
C2 C 0.3211(5) 0.8097(3) 0.21441(12) 0.0186(6) Uani 1 1 d . .
H2A H 0.2080 0.8663 0.1881 0.022 Uiso 1 1 calc R U
C3 C 0.2817(5) 0.8105(3) 0.27284(12) 0.0198(6) Uani 1 1 d . .
H3A H 0.1419 0.8677 0.2865 0.024 Uiso 1 1 calc R U
C4 C 0.4452(5) 0.7281(3) 0.31209(12) 0.0174(6) Uani 1 1 d . .
C5 C 0.6505(5) 0.6446(3) 0.29231(12) 0.0178(6) Uani 1 1 d . .
H5A H 0.7638 0.5890 0.3189 0.021 Uiso 1 1 calc R U
C6 C 0.6880(5) 0.6434(3) 0.23329(12) 0.0173(6) Uani 1 1 d . .
H6A H 0.8266 0.5849 0.2197 0.021 Uiso 1 1 calc R U
C7 C 0.5720(5) 0.7229(3) 0.13052(12) 0.0182(6) Uani 1 1 d . .
C8 C 0.6953(6) 0.5849(3) 0.10595(12) 0.0219(6) Uani 1 1 d . .
C9 C 0.5649(6) 0.6698(3) 0.41237(12) 0.0195(6) Uani 1 1 d . .
H9A H 0.7457 0.7083 0.4095 0.023 Uiso 1 1 calc R U
H9B H 0.5670 0.5601 0.4071 0.023 Uiso 1 1 calc R U
C10 C 0.4679(6) 0.7088(3) 0.47038(12) 0.0215(6) Uani 1 1 d . .
H10A H 0.6008 0.6794 0.5019 0.026 Uiso 1 1 calc R U
H10B H 0.4400 0.8179 0.4729 0.026 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 1.00 0.0060
0.00 0.00 -1.00 0.0040
-1.00 0.00 0.00 0.0870
1.00 2.00 1.00 0.1280
1.00 -2.00 -1.00 0.2330
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 N1 O1 112.9(2)
N1 O1 H1 98(2)
C4 O2 C9 118.2(2)
C10 O3 H3 111(3)
C6 C1 C2 118.0(2)
C6 C1 C7 120.5(2)
C2 C1 C7 121.5(2)
C3 C2 C1 120.6(3)
C3 C2 H2A 119.7
C1 C2 H2A 119.7
C2 C3 C4 120.6(3)
C2 C3 H3A 119.7
C4 C3 H3A 119.7
O2 C4 C5 124.8(2)
O2 C4 C3 115.3(2)
C5 C4 C3 119.9(3)
C6 C5 C4 119.2(3)
C6 C5 H5A 120.4
C4 C5 H5A 120.4
C5 C6 C1 121.7(3)
C5 C6 H6A 119.2
C1 C6 H6A 119.2
N1 C7 C1 130.8(3)
N1 C7 C8 110.6(2)
C1 C7 C8 118.6(2)
F1 C8 F3 106.6(2)
F1 C8 F2 106.2(2)
F3 C8 F2 105.9(2)
F1 C8 C7 112.5(2)
F3 C8 C7 113.5(2)
F2 C8 C7 111.7(2)
O2 C9 C10 107.0(2)
O2 C9 H9A 110.3
C10 C9 H9A 110.3
O2 C9 H9B 110.3
C10 C9 H9B 110.3
H9A C9 H9B 108.6
O3 C10 C9 109.3(2)
O3 C10 H10A 109.8
C9 C10 H10A 109.8
O3 C10 H10B 109.8
C9 C10 H10B 109.8
H10A C10 H10B 108.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C8 1.329(3)
F2 C8 1.356(3)
F3 C8 1.340(3)
N1 C7 1.290(4)
N1 O1 1.380(3)
O1 H1 0.94(4)
O2 C4 1.366(3)
O2 C9 1.434(3)
O3 C10 1.434(3)
O3 H3 0.77(4)
C1 C6 1.400(4)
C1 C2 1.404(4)
C1 C7 1.481(4)
C2 C3 1.376(4)
C2 H2A 0.9500
C3 C4 1.394(4)
C3 H3A 0.9500
C4 C5 1.390(4)
C5 C6 1.388(4)
C5 H5A 0.9500
C6 H6A 0.9500
C7 C8 1.515(4)
C9 C10 1.501(4)
C9 H9A 0.9900
C9 H9B 0.9900
C10 H10A 0.9900
C10 H10B 0.9900
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
O1 H1 O3 0.94(4) 1.76(4) 2.655(3) 160(3) 2
O3 H3 N1 0.77(4) 2.14(4) 2.901(3) 171(4) 4_576
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
C6 C1 C2 C3 0.5(4)
C7 C1 C2 C3 179.6(3)
C1 C2 C3 C4 -0.1(4)
C9 O2 C4 C5 6.6(4)
C9 O2 C4 C3 -173.0(2)
C2 C3 C4 O2 179.9(3)
C2 C3 C4 C5 0.2(4)
O2 C4 C5 C6 179.7(2)
C3 C4 C5 C6 -0.7(4)
C4 C5 C6 C1 1.1(4)
C2 C1 C6 C5 -1.0(4)
C7 C1 C6 C5 179.9(3)
O1 N1 C7 C1 2.1(4)
O1 N1 C7 C8 -177.6(2)
C6 C1 C7 N1 -151.6(3)
C2 C1 C7 N1 29.2(5)
C6 C1 C7 C8 28.1(4)
C2 C1 C7 C8 -151.1(3)
N1 C7 C8 F1 -140.8(3)
C1 C7 C8 F1 39.5(3)
N1 C7 C8 F3 -19.7(3)
C1 C7 C8 F3 160.5(2)
N1 C7 C8 F2 99.9(3)
C1 C7 C8 F2 -79.8(3)
C4 O2 C9 C10 175.1(2)
O2 C9 C10 O3 69.3(3)
