#------------------------------------------------------------------------------
#$Date: 2019-11-26 08:18:42 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243042 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/32/4133205.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_4133205
loop_
_publ_author_name
'Qiu, Dachuan'
'Shi, Jiarong'
'Guo, Qianyu'
'Xu, Qiuxia'
'Li, Baosheng'
'Li, Yang'
_publ_section_title
;
 Cyclohexenynone Precursors: Preparation via Oxidative Dearomatization
 Strategy and Reactivity.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13214
_journal_page_last               13218
_journal_paper_doi               10.1021/jacs.8b08915
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H16 F3 N O4 S'
_chemical_formula_weight         375.36
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6308(7)
_cell_length_b                   13.3546(12)
_cell_length_c                   15.5750(14)
_cell_measurement_reflns_used    2659
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.13
_cell_measurement_theta_min      3.32
_cell_volume                     1795.2(3)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8463
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         3.32
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.823
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.15(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4140
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0699
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0807P)²+0.7659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.2003
_reflns_number_gt                2659
_reflns_number_total             4140
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja8b08915_si_004.cif
_cod_data_source_block           qdc-3
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4133205
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.52545(14) 0.81389(9) 0.88068(7) 0.0552(3) Uani 1 1 d .
C6 C 0.8988(4) 0.8151(3) 0.7679(3) 0.0548(11) Uani 1 1 d .
H6A H 0.8898 0.7458 0.7662 0.066 Uiso 1 1 calc R
N1 N 0.6150(4) 0.8215(3) 0.7900(2) 0.0470(8) Uani 1 1 d .
C7 C 0.7609(5) 0.8751(3) 0.7828(3) 0.0457(10) Uani 1 1 d .
C14 C 0.5932(5) 0.6841(3) 0.6862(3) 0.0553(11) Uani 1 1 d .
H14A H 0.6591 0.6453 0.7197 0.066 Uiso 1 1 calc R
O4 O 0.3656(4) 0.7972(3) 0.8647(2) 0.0798(11) Uani 1 1 d .
F3 F 0.5481(6) 0.6189(2) 0.8828(3) 0.1075(13) Uani 1 1 d .
C13 C 0.5506(5) 0.7789(3) 0.7126(3) 0.0458(9) Uani 1 1 d .
C4 C 1.0546(5) 0.9650(3) 0.7546(3) 0.0569(11) Uani 1 1 d .
F2 F 0.5392(5) 0.6881(3) 1.0074(2) 0.1128(13) Uani 1 1 d .
C8 C 0.7668(6) 0.9730(3) 0.7866(3) 0.0589(12) Uani 1 1 d .
H8A H 0.6751 1.0089 0.7930 0.071 Uiso 1 1 calc R
O1 O 1.1764(4) 1.0050(3) 0.7361(3) 0.0849(13) Uani 1 1 d .
C5 C 1.0375(5) 0.8563(3) 0.7567(3) 0.0584(11) Uani 1 1 d .
H5A H 1.1242 0.8157 0.7500 0.070 Uiso 1 1 calc R
C10 C 0.4377(6) 0.7021(4) 0.5581(3) 0.0658(13) Uani 1 1 d .
O2 O 0.9080(6) 1.1160(3) 0.7473(4) 0.1136(17) Uani 1 1 d U
C11 C 0.3947(6) 0.7979(5) 0.5875(3) 0.0707(15) Uani 1 1 d .
H11A H 0.3269 0.8365 0.5550 0.085 Uiso 1 1 calc R
C15 C 0.5363(6) 0.6475(3) 0.6086(3) 0.0632(12) Uani 1 1 d .
H15A H 0.5662 0.5840 0.5905 0.076 Uiso 1 1 calc R
C12 C 0.4516(6) 0.8353(4) 0.6640(3) 0.0603(12) Uani 1 1 d .
H12A H 0.4226 0.8988 0.6824 0.072 Uiso 1 1 calc R
F1 F 0.7446(4) 0.6942(4) 0.9319(3) 0.1196(14) Uani 1 1 d .
O3 O 0.5791(5) 0.8887(3) 0.9357(2) 0.0848(12) Uani 1 1 d .
C3 C 0.9158(6) 1.0285(4) 0.7808(5) 0.0780(14) Uani 1 1 d U
C16 C 0.5934(7) 0.6955(5) 0.9278(4) 0.0760(15) Uani 1 1 d .
C2 C 0.9593(8) 1.0686(5) 0.8810(5) 0.104(2) Uani 1 1 d U
H2A H 0.8764 1.1096 0.9022 0.156 Uiso 1 1 calc R
H2B H 1.0533 1.1071 0.8794 0.156 Uiso 1 1 calc R
H2C H 0.9730 1.0119 0.9181 0.156 Uiso 1 1 calc R
C9 C 0.3801(9) 0.6617(6) 0.4715(4) 0.110(3) Uani 1 1 d .
H9A H 0.3122 0.7098 0.4454 0.166 Uiso 1 1 calc R
H9B H 0.3249 0.6001 0.4805 0.166 Uiso 1 1 calc R
H9C H 0.4670 0.6498 0.4344 0.166 Uiso 1 1 calc R
C1 C 0.8787(9) 1.0924(5) 0.6541(6) 0.114(2) Uani 1 1 d U
H1A H 0.8716 1.1536 0.6220 0.171 Uiso 1 1 calc R
H1B H 0.7833 1.0559 0.6487 0.171 Uiso 1 1 calc R
H1C H 0.9624 1.0526 0.6320 0.171 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 0.0033 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 S1 O4 122.9(3)
O3 S1 N1 109.5(2)
O4 S1 N1 108.8(2)
O3 S1 C16 105.3(3)
O4 S1 C16 104.2(3)
N1 S1 C16 104.6(2)
C5 C6 C7 122.1(4)
C13 N1 C7 117.6(3)
C13 N1 S1 121.5(3)
C7 N1 S1 120.9(3)
C8 C7 N1 121.5(4)
C8 C7 C6 121.7(4)
N1 C7 C6 116.8(3)
C13 C14 C15 119.1(4)
C12 C13 C14 120.4(4)
C12 C13 N1 119.0(4)
C14 C13 N1 120.5(4)
O1 C4 C5 122.0(4)
O1 C4 C3 119.9(4)
C5 C4 C3 118.0(4)
C7 C8 C3 121.9(4)
C6 C5 C4 120.4(4)
C15 C10 C11 117.5(5)
C15 C10 C9 121.2(6)
C11 C10 C9 121.3(6)
C3 O2 C1 102.1(5)
C12 C11 C10 121.0(5)
C10 C15 C14 122.0(4)
C13 C12 C11 120.0(5)
O2 C3 C8 115.7(5)
O2 C3 C4 116.1(5)
C8 C3 C4 114.7(4)
O2 C3 C2 95.7(5)
C8 C3 C2 107.1(5)
C4 C3 C2 104.4(5)
F3 C16 F1 108.4(6)
F3 C16 F2 109.8(5)
F1 C16 F2 107.8(5)
F3 C16 S1 111.4(4)
F1 C16 S1 110.4(4)
F2 C16 S1 108.9(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.396(4)
S1 O4 1.419(4)
S1 N1 1.614(4)
S1 C16 1.839(6)
C6 C5 1.329(6)
C6 C7 1.454(6)
N1 C13 1.444(5)
N1 C7 1.453(5)
C7 C8 1.310(6)
C14 C13 1.381(6)
C14 C15 1.394(6)
F3 C16 1.301(7)
C13 C12 1.367(6)
C4 O1 1.214(5)
C4 C5 1.459(6)
C4 C3 1.523(7)
F2 C16 1.328(7)
C8 C3 1.487(7)
C10 C15 1.369(7)
C10 C11 1.408(8)
C10 C9 1.537(8)
O2 C3 1.281(7)
O2 C1 1.508(10)
C11 C12 1.382(7)
F1 C16 1.307(6)
C3 C2 1.692(10)
