#------------------------------------------------------------------------------
#$Date: 2020-08-06 16:03:31 +0300 (Thu, 06 Aug 2020) $
#$Revision: 254908 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/67/7126729.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_7126729
loop_
_publ_author_name
'Yuan, Hairui'
'Du, Yuanbo'
'Liu, Fengting'
'Guo, Lirong'
'Sun, Qianyu'
'Feng, Lei'
'Gao, Hongyin'
_publ_section_title
;
 Tandem approach to NOBIN analogues from arylhydroxylamines and
 diaryliodonium salts via [3,3]-sigmatropic rearrangement.
;
_journal_issue                   59
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8226
_journal_page_last               8229
_journal_paper_doi               10.1039/d0cc02919j
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C24 H16 F3 N O2'
_chemical_formula_sum            'C24 H16 F3 N O2'
_chemical_formula_weight         407.38
_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_date             2018-10-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2020-03-09 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.910(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0044(8)
_cell_length_b                   8.2203(3)
_cell_length_c                   19.4734(10)
_cell_measurement_reflns_used    3629
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      76.4970
_cell_measurement_theta_min      4.7410
_cell_volume                     2272.2(2)
_computing_cell_refinement
'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction
'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00  26.00   1.00    0.70    --  -48.45  15.00  44.00   74
  2  ω   -123.00 -38.00   1.00    0.70    --  -48.45 -15.00-126.00   85
  3  ω     55.00  81.00   1.00    0.70    --   48.45  15.00  44.00   26
  4  ω    -19.00   7.00   1.00    0.70    --   48.45 -15.00-126.00   26
  5  ω    -80.00 -55.00   1.00    6.00    --  -86.25  15.00  44.00   25
  6  ω   -142.00-101.00   1.00    6.00    --  -86.25 -15.00-126.00   41
  7  ω     97.00 176.00   1.00    6.00    --  107.75  15.00  44.00   79
  8  ω     34.00 108.00   1.00    6.00    --  107.75 -15.00-126.00   74
  9  ω    -24.00  61.00   1.00    0.70    --   48.45 -37.00 120.00   85
 10  ω     35.00 120.00   1.00    6.00    --  107.75 -37.00-150.00   85
 11  ω     35.00 117.00   1.00    6.00    --  107.75-125.00-120.00   82
 12  ω     49.00 108.00   1.00    6.00    --  107.75 -99.00   0.00   59
 13  ω     35.00 109.00   1.00    6.00    --  107.75 -99.00-120.00   74
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0003964000
_diffrn_orient_matrix_UB_12      0.0281041000
_diffrn_orient_matrix_UB_13      0.0783227000
_diffrn_orient_matrix_UB_21      -0.1076527000
_diffrn_orient_matrix_UB_22      -0.0237017000
_diffrn_orient_matrix_UB_23      -0.0251212000
_diffrn_orient_matrix_UB_31      0.0140803000
_diffrn_orient_matrix_UB_32      -0.1836957000
_diffrn_orient_matrix_UB_33      0.0152125000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12336
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.059
_diffrn_reflns_theta_min         3.257
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.191
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0666
_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)+(0.1121P)²+0.7710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1903
_refine_ls_wR_factor_ref         0.2101
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2986
_reflns_number_total             4025
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc02919j2.cif
_cod_data_source_block           181016a_sq_s
_cod_depositor_comments
'Adding full bibliography for 7126729--7126730.cif.'
_cod_database_code               7126729
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         CNOF
_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 99.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C23(H23), C4(H4), C20(H20), C17(H17), C8(H8), C1(H1B), C3(H3),
 C13(H13), C21(H21), C2(H2), C7(H7), C14(H14), C16(H16), C15(H15)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.272
_oxdiff_exptl_absorpt_empirical_full_min 0.642
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.53369(14) 0.2214(2) 0.63131(10) 0.0551(5) Uani 1 1 d . . . . .
H1 H 0.5101 0.1305 0.6277 0.083 Uiso 1 1 calc GR . . . .
O2 O 0.46179(14) 0.9184(2) 0.60765(11) 0.0608(5) Uani 1 1 d . . . . .
N1 N 0.44757(15) 0.6911(2) 0.54182(11) 0.0483(5) Uani 1 1 d . . . . .
H1A H 0.4095 0.6239 0.5129 0.058 Uiso 1 1 calc R . . . .
C10 C 0.57820(16) 0.5513(3) 0.63159(12) 0.0401(5) Uani 1 1 d . . . . .
C5 C 0.67740(17) 0.5204(3) 0.66067(13) 0.0426(5) Uani 1 1 d . . . . .
C18 C 0.51302(17) 0.4858(3) 0.66866(13) 0.0432(5) Uani 1 1 d . . . . .
C11 C 0.41338(18) 0.8311(3) 0.55775(13) 0.0454(6) Uani 1 1 d . . . . .
C9 C 0.54499(18) 0.6490(3) 0.57110(13) 0.0456(6) Uani 1 1 d . . . . .
C12 C 0.31487(19) 0.8759(3) 0.51461(14) 0.0491(6) Uani 1 1 d . . . . .
C19 C 0.49201(17) 0.3206(3) 0.66764(14) 0.0451(6) Uani 1 1 d . . . . .
C23 C 0.47215(18) 0.5902(3) 0.70570(14) 0.0485(6) Uani 1 1 d . . . . .
H23 H 0.4858 0.7007 0.7070 0.058 Uiso 1 1 calc R . . . .
C6 C 0.73868(18) 0.5887(3) 0.62617(14) 0.0488(6) Uani 1 1 d . . . . .
C4 C 0.71784(19) 0.4304(3) 0.72527(15) 0.0517(6) Uani 1 1 d . . . . .
H4 H 0.6790 0.3835 0.7485 0.062 Uiso 1 1 calc R . . . .
F1 F 0.3417(3) 0.7860(4) 0.7450(2) 0.1625(17) Uani 1 1 d . . . . .
C22 C 0.4115(2) 0.5336(4) 0.74073(16) 0.0579(7) Uani 1 1 d . . . . .
C20 C 0.4314(2) 0.2635(3) 0.70264(17) 0.0594(7) Uani 1 1 d . . . . .
H20 H 0.4173 0.1531 0.7012 0.071 Uiso 1 1 calc R . . . .
C17 C 0.2605(2) 0.9570(4) 0.54924(17) 0.0623(7) Uani 1 1 d . . . . .
H17 H 0.2855 0.9802 0.5985 0.075 Uiso 1 1 calc R . . . .
C8 C 0.6068(2) 0.7149(3) 0.53706(15) 0.0580(7) Uani 1 1 d . . . . .
H8 H 0.5830 0.7799 0.4961 0.070 Uiso 1 1 calc R . . . .
C1 C 0.8369(2) 0.5640(4) 0.65677(18) 0.0599(7) Uani 1 1 d . . . . .
H1B H 0.8772 0.6067 0.6338 0.072 Uiso 1 1 calc R . . . .
C3 C 0.8129(2) 0.4117(3) 0.75371(18) 0.0628(8) Uani 1 1 d . . . . .
H3 H 0.8382 0.3536 0.7966 0.075 Uiso 1 1 calc R . . . .
C13 C 0.2779(2) 0.8438(4) 0.44084(16) 0.0614(7) Uani 1 1 d . . . . .
H13 H 0.3140 0.7897 0.4172 0.074 Uiso 1 1 calc R . . . .
C21 C 0.3917(2) 0.3687(4) 0.73954(19) 0.0641(8) Uani 1 1 d . . . . .
H21 H 0.3518 0.3292 0.7636 0.077 Uiso 1 1 calc R . . . .
C2 C 0.8731(2) 0.4786(4) 0.71934(19) 0.0653(8) Uani 1 1 d . . . . .
H2 H 0.9379 0.4645 0.7394 0.078 Uiso 1 1 calc R . . . .
C7 C 0.7003(2) 0.6844(4) 0.56354(16) 0.0621(7) Uani 1 1 d . . . . .
H7 H 0.7399 0.7272 0.5400 0.075 Uiso 1 1 calc R . . . .
F2 F 0.2970(3) 0.5977(4) 0.7941(3) 0.181(2) Uani 1 1 d . . . . .
C24 C 0.3681(3) 0.6498(5) 0.7781(2) 0.0784(10) Uani 1 1 d . . . . .
C14 C 0.1872(3) 0.8924(4) 0.4026(2) 0.0788(10) Uani 1 1 d . . . . .
H14 H 0.1625 0.8719 0.3530 0.095 Uiso 1 1 calc R . . . .
F3 F 0.4255(3) 0.7003(7) 0.8401(2) 0.217(3) Uani 1 1 d . . . . .
C16 C 0.1696(2) 1.0034(5) 0.5110(2) 0.0797(10) Uani 1 1 d . . . . .
H16 H 0.1330 1.0562 0.5346 0.096 Uiso 1 1 calc R . . . .
C15 C 0.1332(2) 0.9711(5) 0.4376(2) 0.0851(11) Uani 1 1 d . . . . .
H15 H 0.0719 1.0025 0.4117 0.102 Uiso 1 1 calc R . . . .
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'
F F 0.0727 0.0534 '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'
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
C19 O1 H1 109.5 . . ?
C11 N1 H1A 118.8 . . ?
C11 N1 C9 122.4(2) . . ?
C9 N1 H1A 118.8 . . ?
C5 C10 C18 120.3(2) . . ?
C9 C10 C5 118.8(2) . . ?
C9 C10 C18 120.8(2) . . ?
C6 C5 C10 119.5(2) . . ?
C4 C5 C10 122.3(2) . . ?
C4 C5 C6 118.1(2) . . ?
C19 C18 C10 121.7(2) . . ?
C23 C18 C10 119.9(2) . . ?
C23 C18 C19 118.4(2) . . ?
O2 C11 N1 120.7(2) . . ?
O2 C11 C12 121.5(2) . . ?
N1 C11 C12 117.9(2) . . ?
C10 C9 N1 121.5(2) . . ?
C10 C9 C8 121.0(2) . . ?
C8 C9 N1 117.5(2) . . ?
C17 C12 C11 118.5(2) . . ?
C17 C12 C13 119.6(3) . . ?
C13 C12 C11 121.8(2) . . ?
O1 C19 C18 116.9(2) . . ?
O1 C19 C20 122.7(2) . . ?
C20 C19 C18 120.4(2) . . ?
C18 C23 H23 119.3 . . ?
C22 C23 C18 121.4(2) . . ?
C22 C23 H23 119.3 . . ?
C1 C6 C5 119.4(2) . . ?
C7 C6 C5 119.0(2) . . ?
C7 C6 C1 121.5(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C23 C22 C21 119.5(3) . . ?
C23 C22 C24 119.5(3) . . ?
C21 C22 C24 121.1(3) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.6(2) . . ?
C21 C20 H20 119.7 . . ?
C12 C17 H17 119.8 . . ?
C16 C17 C12 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
C9 C8 H8 119.7 . . ?
C7 C8 C9 120.5(2) . . ?
C7 C8 H8 119.7 . . ?
C6 C1 H1B 119.6 . . ?
C2 C1 C6 120.8(3) . . ?
C2 C1 H1B 119.6 . . ?
C4 C3 H3 119.5 . . ?
C4 C3 C2 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C22 C21 H21 120.1 . . ?
C20 C21 C22 119.8(3) . . ?
C20 C21 H21 120.1 . . ?
C1 C2 C3 120.0(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.1(3) . . ?
C8 C7 H7 119.5 . . ?
F1 C24 C22 115.5(3) . . ?
F1 C24 F3 101.0(4) . . ?
F2 C24 F1 105.5(4) . . ?
F2 C24 C22 116.2(4) . . ?
F2 C24 F3 103.4(4) . . ?
F3 C24 C22 113.6(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
C17 C16 H16 120.1 . . ?
C17 C16 C15 119.8(3) . . ?
C15 C16 H16 120.1 . . ?
C14 C15 C16 120.2(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
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
O1 H1 0.8200 . ?
O1 C19 1.358(3) . ?
O2 C11 1.237(3) . ?
N1 H1A 0.8600 . ?
N1 C11 1.337(3) . ?
N1 C9 1.429(3) . ?
C10 C5 1.433(3) . ?
C10 C18 1.492(3) . ?
C10 C9 1.378(3) . ?
C5 C6 1.418(4) . ?
C5 C4 1.415(3) . ?
C18 C19 1.392(3) . ?
C18 C23 1.386(4) . ?
C11 C12 1.490(4) . ?
C9 C8 1.411(4) . ?
C12 C17 1.386(4) . ?
C12 C13 1.387(4) . ?
C19 C20 1.383(4) . ?
C23 H23 0.9300 . ?
C23 C22 1.383(4) . ?
C6 C1 1.414(4) . ?
C6 C7 1.408(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.361(4) . ?
F1 C24 1.288(5) . ?
C22 C21 1.387(4) . ?
C22 C24 1.473(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.377(4) . ?
C17 H17 0.9300 . ?
C17 C16 1.379(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.353(4) . ?
C1 H1B 0.9300 . ?
C1 C2 1.358(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.400(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(5) . ?
C21 H21 0.9300 . ?
C2 H2 0.9300 . ?
C7 H7 0.9300 . ?
F2 C24 1.280(5) . ?
C24 F3 1.303(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(6) . ?
C16 H16 0.9300 . ?
C16 C15 1.381(6) . ?
C15 H15 0.9300 . ?
