#------------------------------------------------------------------------------
#$Date: 2020-02-26 01:41:52 +0200 (Wed, 26 Feb 2020) $
#$Revision: 248436 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/42/4134237.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_4134237
loop_
_publ_author_name
'Deng, Tianning'
'Mazumdar, Wrickban'
'Ford, Russell'
'Jana, Navendu'
'Izar, Ragda'
'Wink, Donald J.'
'Driver, Tom G.'
_publ_section_title
;
 Oxidation of Non-Activated Anilines to Generate N-Aryl Nitrenoids.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b13599
_journal_year                    2020
_chemical_formula_sum            'C21 H22 Cl F3 N O2'
_chemical_formula_weight         412.84
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                101.790(6)
_cell_angle_beta                 108.779(6)
_cell_angle_gamma                110.077(5)
_cell_formula_units_Z            2
_cell_length_a                   9.358(2)
_cell_length_b                   10.445(3)
_cell_length_c                   12.247(3)
_cell_measurement_temperature    296(2)
_cell_volume                     995.5(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0803
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10837
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        23.970
_diffrn_reflns_theta_max         23.970
_diffrn_reflns_theta_min         1.878
_exptl_absorpt_coefficient_mu    0.236
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             430
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.0715
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1767
_refine_ls_wR_factor_ref         0.1955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1991
_reflns_number_total             3067
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b13599_si_003.cif
_cod_data_source_block           cdwtd28_0m_a
_cod_database_code               4134237
_shelx_shelxl_version_number     2014/7
_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   0.899
_shelx_estimated_absorpt_t_max   0.977
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F4 F 0.4642(6) 0.9628(5) 0.1396(4) 0.1384(17) Uani 1 1 d . . . . .
Cl01 Cl 0.32603(15) 0.62328(13) 0.45909(10) 0.0575(4) Uani 1 1 d . . . . .
N002 N 0.5395(4) 0.5325(3) 0.3405(3) 0.0349(8) Uani 1 1 d . . . . .
H002 H 0.5094 0.5722 0.3922 0.042 Uiso 1 1 calc R U . . .
F1 F 0.4235(5) 1.0726(3) 0.2788(3) 0.1066(12) Uani 1 1 d . . . . .
O1 O 0.4822(5) 0.7804(4) 0.2549(4) 0.0845(12) Uani 1 1 d . . . . .
C005 C 0.4263(5) 0.4084(4) 0.2331(4) 0.0356(10) Uani 1 1 d . . . . .
O2 O 0.3154(5) 0.8264(4) 0.3347(4) 0.0934(13) Uani 1 1 d . . . . .
C007 C 0.8294(5) 0.7097(4) 0.4556(4) 0.0372(10) Uani 1 1 d . . . . .
C008 C 0.6932(5) 0.5803(4) 0.3530(3) 0.0363(10) Uani 1 1 d . . . . .
F5 F 0.2226(5) 0.9004(4) 0.1277(4) 0.1365(17) Uani 1 1 d . . . . .
C00A C 0.5161(5) 0.3762(4) 0.1711(4) 0.0352(10) Uani 1 1 d . . . . .
C00B C 0.7011(4) 0.4857(4) 0.2446(3) 0.0349(10) Uani 1 1 d . . . . .
C00C C 0.7643(5) 0.5795(4) 0.1715(4) 0.0426(10) Uani 1 1 d . . . . .
H00C H 0.6827 0.6139 0.1359 0.051 Uiso 1 1 calc R U . . .
H00D H 0.8692 0.6641 0.2281 0.051 Uiso 1 1 calc R U . . .
C00D C 0.8116(5) 0.4074(4) 0.2868(4) 0.0389(10) Uani 1 1 d . . . . .
H00E H 0.9195 0.4787 0.3530 0.047 Uiso 1 1 calc R U . . .
H00F H 0.7575 0.3373 0.3189 0.047 Uiso 1 1 calc R U . . .
C00E C 0.2575(5) 0.3301(5) 0.1970(4) 0.0447(11) Uani 1 1 d . . . . .
H00G H 0.2037 0.3554 0.2437 0.054 Uiso 1 1 calc R U . . .
C00G C 0.9978(5) 0.7559(5) 0.4748(4) 0.0512(12) Uani 1 1 d . . . . .
H00J H 1.0246 0.7020 0.4211 0.061 Uiso 1 1 calc R U . . .
C00H C 0.8407(5) 0.3294(5) 0.1831(4) 0.0519(12) Uani 1 1 d . . . . .
H00K H 0.7354 0.2475 0.1230 0.062 Uiso 1 1 calc R U . . .
H00L H 0.9197 0.2915 0.2161 0.062 Uiso 1 1 calc R U . . .
C00I C 0.3975(6) 0.8394(5) 0.2682(4) 0.0571(13) Uani 1 1 d . . . . .
C00J C 0.1719(5) 0.2132(5) 0.0893(4) 0.0543(12) Uani 1 1 d . . . . .
H00M H 0.0569 0.1572 0.0610 0.065 Uiso 1 1 calc R U . . .
C00K C 0.2553(6) 0.1772(5) 0.0217(4) 0.0536(12) Uani 1 1 d . . . . .
H00N H 0.1954 0.0975 -0.0517 0.064 Uiso 1 1 calc R U . . .
C00L C 0.7923(6) 0.4963(5) 0.0689(4) 0.0565(12) Uani 1 1 d . . . . .
H00O H 0.6852 0.4192 0.0060 0.068 Uiso 1 1 calc R U . . .
H00P H 0.8405 0.5618 0.0310 0.068 Uiso 1 1 calc R U . . .
C00M C 0.4267(5) 0.2587(5) 0.0624(4) 0.0479(11) Uani 1 1 d . . . . .
H00Q H 0.4813 0.2339 0.0162 0.057 Uiso 1 1 calc R U . . .
C00O C 0.9093(6) 0.4309(5) 0.1196(4) 0.0578(13) Uani 1 1 d . . . . .
H00R H 1.0187 0.5087 0.1782 0.069 Uiso 1 1 calc R U . . .
H00S H 0.9236 0.3769 0.0527 0.069 Uiso 1 1 calc R U . . .
C00P C 0.7959(6) 0.7955(5) 0.5393(4) 0.0515(12) Uani 1 1 d . . . . .
H00T H 0.6861 0.7687 0.5304 0.062 Uiso 1 1 calc R U . . .
C00Q C 1.1229(6) 0.8782(5) 0.5706(5) 0.0613(13) Uani 1 1 d . . . . .
H00U H 1.2340 0.9060 0.5825 0.074 Uiso 1 1 calc R U . . .
C00R C 1.0859(7) 0.9598(5) 0.6488(4) 0.0641(14) Uani 1 1 d . . . . .
H00V H 1.1713 1.0443 0.7131 0.077 Uiso 1 1 calc R U . . .
C00S C 0.9236(7) 0.9173(5) 0.6328(5) 0.0676(14) Uani 1 1 d . . . . .
H00W H 0.8997 0.9731 0.6875 0.081 Uiso 1 1 calc R U . . .
C1 C 0.3781(7) 0.9451(6) 0.2045(5) 0.0643(14) 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C008 N002 C005 113.0(3) . . ?
C008 N002 H002 123.5 . . ?
C005 N002 H002 123.5 . . ?
C00E C005 C00A 125.2(4) . . ?
C00E C005 N002 126.7(4) . . ?
C00A C005 N002 108.0(3) . . ?
C00G C007 C00P 117.0(4) . . ?
C00G C007 C008 122.3(4) . . ?
C00P C007 C008 120.8(4) . . ?
N002 C008 C007 122.0(3) . . ?
N002 C008 C00B 109.6(3) . . ?
C007 C008 C00B 128.4(3) . . ?
C00M C00A C005 116.7(4) . . ?
C00M C00A C00B 134.5(3) . . ?
C005 C00A C00B 108.8(3) . . ?
C008 C00B C00A 100.6(3) . . ?
C008 C00B C00C 109.7(3) . . ?
C00A C00B C00C 111.8(3) . . ?
C008 C00B C00D 111.9(3) . . ?
C00A C00B C00D 110.8(3) . . ?
C00C C00B C00D 111.5(3) . . ?
C00L C00C C00B 113.0(3) . . ?
C00L C00C H00C 109.0 . . ?
C00B C00C H00C 109.0 . . ?
C00L C00C H00D 109.0 . . ?
C00B C00C H00D 109.0 . . ?
H00C C00C H00D 107.8 . . ?
C00H C00D C00B 112.7(3) . . ?
C00H C00D H00E 109.1 . . ?
C00B C00D H00E 109.1 . . ?
C00H C00D H00F 109.1 . . ?
C00B C00D H00F 109.1 . . ?
H00E C00D H00F 107.8 . . ?
C00J C00E C005 116.9(4) . . ?
C00J C00E H00G 121.6 . . ?
C005 C00E H00G 121.6 . . ?
C00Q C00G C007 121.3(4) . . ?
C00Q C00G H00J 119.4 . . ?
C007 C00G H00J 119.4 . . ?
C00D C00H C00O 111.6(3) . . ?
C00D C00H H00K 109.3 . . ?
C00O C00H H00K 109.3 . . ?
C00D C00H H00L 109.3 . . ?
C00O C00H H00L 109.3 . . ?
H00K C00H H00L 108.0 . . ?
O1 C00I O2 127.8(5) . . ?
O1 C00I C1 120.5(5) . . ?
O2 C00I C1 111.7(4) . . ?
C00E C00J C00K 120.4(4) . . ?
C00E C00J H00M 119.8 . . ?
C00K C00J H00M 119.8 . . ?
C00M C00K C00J 120.7(4) . . ?
C00M C00K H00N 119.6 . . ?
C00J C00K H00N 119.6 . . ?
C00O C00L C00C 110.6(3) . . ?
C00O C00L H00O 109.5 . . ?
C00C C00L H00O 109.5 . . ?
C00O C00L H00P 109.5 . . ?
C00C C00L H00P 109.5 . . ?
H00O C00L H00P 108.1 . . ?
C00A C00M C00K 120.0(4) . . ?
C00A C00M H00Q 120.0 . . ?
C00K C00M H00Q 120.0 . . ?
C00L C00O C00H 111.5(3) . . ?
C00L C00O H00R 109.3 . . ?
C00H C00O H00R 109.3 . . ?
C00L C00O H00S 109.3 . . ?
C00H C00O H00S 109.3 . . ?
H00R C00O H00S 108.0 . . ?
C00S C00P C007 120.1(4) . . ?
C00S C00P H00T 120.0 . . ?
C007 C00P H00T 120.0 . . ?
C00R C00Q C00G 120.2(5) . . ?
C00R C00Q H00U 119.9 . . ?
C00G C00Q H00U 119.9 . . ?
C00Q C00R C00S 119.8(5) . . ?
C00Q C00R H00V 120.1 . . ?
C00S C00R H00V 120.1 . . ?
C00P C00S C00R 121.6(5) . . ?
C00P C00S H00W 119.2 . . ?
C00R C00S H00W 119.2 . . ?
F1 C1 F4 106.5(5) . . ?
F1 C1 F5 106.1(5) . . ?
F4 C1 F5 105.8(5) . . ?
F1 C1 C00I 113.6(4) . . ?
F4 C1 C00I 112.6(4) . . ?
F5 C1 C00I 111.7(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F4 C1 1.298(6) . ?
N002 C008 1.294(4) . ?
N002 C005 1.413(5) . ?
N002 H002 0.8600 . ?
F1 C1 1.284(5) . ?
O1 C00I 1.188(5) . ?
C005 C00E 1.370(5) . ?
C005 C00A 1.376(5) . ?
O2 C00I 1.284(6) . ?
C007 C00G 1.402(6) . ?
C007 C00P 1.405(6) . ?
C007 C008 1.457(5) . ?
C008 C00B 1.523(5) . ?
F5 C1 1.301(6) . ?
C00A C00M 1.374(5) . ?
C00A C00B 1.527(5) . ?
C00B C00C 1.553(5) . ?
C00B C00D 1.554(5) . ?
C00C C00L 1.524(6) . ?
C00C H00C 0.9700 . ?
C00C H00D 0.9700 . ?
C00D C00H 1.517(5) . ?
C00D H00E 0.9700 . ?
C00D H00F 0.9700 . ?
C00E C00J 1.365(6) . ?
C00E H00G 0.9300 . ?
C00G C00Q 1.362(6) . ?
C00G H00J 0.9300 . ?
C00H C00O 1.528(6) . ?
C00H H00K 0.9700 . ?
C00H H00L 0.9700 . ?
C00I C1 1.504(7) . ?
C00J C00K 1.387(6) . ?
C00J H00M 0.9300 . ?
C00K C00M 1.386(6) . ?
C00K H00N 0.9300 . ?
C00L C00O 1.516(6) . ?
C00L H00O 0.9700 . ?
C00L H00P 0.9700 . ?
C00M H00Q 0.9300 . ?
C00O H00R 0.9700 . ?
C00O H00S 0.9700 . ?
C00P C00S 1.356(6) . ?
C00P H00T 0.9300 . ?
C00Q C00R 1.359(6) . ?
C00Q H00U 0.9300 . ?
C00R C00S 1.361(7) . ?
C00R H00V 0.9300 . ?
C00S H00W 0.9300 . ?
