#------------------------------------------------------------------------------
#$Date: 2020-04-03 02:31:36 +0300 (Fri, 03 Apr 2020) $
#$Revision: 249984 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038173.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_4038173
loop_
_publ_author_name
'François, Benjamin'
'Eberlin, Ludovic'
'Berrée, Fabienne'
'Whiting, Andrew'
'Carboni, Bertrand'
_publ_section_title
;
 Access to Fused Pyrroles from Cyclic 1,3-Dienyl Boronic Esters and
 Arylnitroso Compounds.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03214
_journal_year                    2020
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H20 N2 O2 S'
_chemical_formula_sum            'C20 H20 N2 O2 S'
_chemical_formula_weight         352.44
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 103.123(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.986(4)
_cell_length_b                   9.394(3)
_cell_length_c                   17.213(7)
_cell_measurement_reflns_used    829
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.3497
_cell_measurement_theta_min      2.9586
_cell_measurement_wavelength     0.710730
_cell_volume                     1730.0(11)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
'PLATON, A.L.Spek, Acta Cryst. 2009, D65, 148-155'
_computing_publication_material
'CRYSCALC (T. Roisnel, local program, ver. 2020)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      0.0754486
_diffrn_orient_matrix_UB_12      -0.0244227
_diffrn_orient_matrix_UB_13      0.0425289
_diffrn_orient_matrix_UB_21      0.0498557
_diffrn_orient_matrix_UB_22      -0.0118247
_diffrn_orient_matrix_UB_23      -0.0414924
_diffrn_orient_matrix_UB_31      0.0236276
_diffrn_orient_matrix_UB_32      0.1029386
_diffrn_orient_matrix_UB_33      0.0053239
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1128
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.596
_diffrn_reflns_theta_min         2.430
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0486
_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)+(0.0544P)²+1.0504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2808
_reflns_number_total             3974
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b03214_si_003.cif
_cod_data_source_block           BF3_129x2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038173
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
S1 S 0.21489(5) 0.41534(5) 0.14779(3) 0.01892(15) Uani 1 1 d . . . . .
O2 O 0.33818(14) 0.41424(16) 0.19775(9) 0.0249(4) Uani 1 1 d . . . . .
O3 O 0.17064(15) 0.54051(16) 0.10210(9) 0.0264(4) Uani 1 1 d . . . . .
N1 N 0.17903(17) -0.03610(18) -0.08027(10) 0.0192(4) Uani 1 1 d . . . . .
N2 N 0.20758(17) 0.28360(18) 0.08424(10) 0.0182(4) Uani 1 1 d . . . . .
C1 C 0.4192(2) -0.3769(3) -0.09861(16) 0.0326(6) Uani 1 1 d . . . . .
H1 H 0.474755 -0.452926 -0.102110 0.039 Uiso 1 1 calc R U . . .
C2 C 0.4100(2) -0.2621(3) -0.14990(15) 0.0311(6) Uani 1 1 d . . . . .
H2 H 0.457796 -0.260124 -0.189498 0.037 Uiso 1 1 calc R U . . .
C3 C 0.3309(2) -0.1497(2) -0.14344(14) 0.0263(5) Uani 1 1 d . . . . .
H3 H 0.325196 -0.070436 -0.178362 0.032 Uiso 1 1 calc R U . . .
C4 C 0.2603(2) -0.1527(2) -0.08630(12) 0.0187(5) Uani 1 1 d . . . . .
C5 C 0.2679(2) -0.2688(2) -0.03552(13) 0.0229(5) Uani 1 1 d . . . . .
H5 H 0.218970 -0.271449 0.003442 0.028 Uiso 1 1 calc R U . . .
C6 C 0.3472(2) -0.3809(3) -0.04196(14) 0.0298(6) Uani 1 1 d . . . . .
H6 H 0.352219 -0.460729 -0.007493 0.036 Uiso 1 1 calc R U . . .
C7 C 0.0796(2) 0.0096(2) -0.13875(13) 0.0220(5) Uani 1 1 d . . . . .
H7 H 0.050579 -0.033667 -0.189459 0.026 Uiso 1 1 calc R U . . .
C8 C 0.0295(2) 0.1280(2) -0.11163(13) 0.0222(5) Uani 1 1 d . . . . .
H8 H -0.040557 0.180755 -0.139627 0.027 Uiso 1 1 calc R U . . .
C9 C 0.1014(2) 0.1570(2) -0.03436(12) 0.0186(5) Uani 1 1 d . . . . .
C10 C 0.1925(2) 0.0556(2) -0.01609(12) 0.0184(5) Uani 1 1 d . . . . .
C11 C 0.2937(2) 0.0514(2) 0.05759(13) 0.0230(5) Uani 1 1 d . . . . .
H11A H 0.372526 0.088358 0.046642 0.028 Uiso 1 1 calc R U . . .
H11B H 0.307935 -0.047704 0.077144 0.028 Uiso 1 1 calc R U . . .
C12 C 0.2526(2) 0.1438(2) 0.11981(12) 0.0200(5) Uani 1 1 d . . . . .
H12A H 0.184770 0.095438 0.138905 0.024 Uiso 1 1 calc R U . . .
H12B H 0.323691 0.158300 0.166046 0.024 Uiso 1 1 calc R U . . .
C13 C 0.0890(2) 0.2736(2) 0.02295(13) 0.0218(5) Uani 1 1 d . . . . .
H13A H 0.071376 0.365211 -0.005852 0.026 Uiso 1 1 calc R U . . .
H13B H 0.018985 0.252409 0.048599 0.026 Uiso 1 1 calc R U . . .
C14 C 0.1082(2) 0.3747(2) 0.20732(12) 0.0173(4) Uani 1 1 d . . . . .
C15 C -0.0142(2) 0.4229(2) 0.18511(12) 0.0196(5) Uani 1 1 d . . . . .
H15 H -0.039611 0.483073 0.139958 0.023 Uiso 1 1 calc R U . . .
C16 C -0.0989(2) 0.3825(2) 0.22939(13) 0.0219(5) Uani 1 1 d . . . . .
H16 H -0.182920 0.414443 0.213823 0.026 Uiso 1 1 calc R U . . .
C17 C -0.0633(2) 0.2957(2) 0.29647(13) 0.0198(5) Uani 1 1 d . . . . .
C18 C 0.0597(2) 0.2486(2) 0.31725(12) 0.0198(5) Uani 1 1 d . . . . .
H18 H 0.085348 0.188743 0.362492 0.024 Uiso 1 1 calc R U . . .
C19 C 0.1458(2) 0.2872(2) 0.27338(12) 0.0193(5) Uani 1 1 d . . . . .
H19 H 0.229598 0.254044 0.288330 0.023 Uiso 1 1 calc R U . . .
C20 C -0.1555(2) 0.2530(3) 0.34497(15) 0.0312(6) Uani 1 1 d . . . . .
H20A H -0.170992 0.150374 0.339558 0.047 Uiso 1 1 calc R U . . .
H20B H -0.234134 0.304568 0.325716 0.047 Uiso 1 1 calc R U . . .
H20C H -0.121410 0.276382 0.401194 0.047 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 0.0033 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 119.45(10) . . ?
O2 S1 N2 106.96(9) . . ?
O3 S1 N2 107.03(10) . . ?
O2 S1 C14 108.20(10) . . ?
O3 S1 C14 107.94(10) . . ?
N2 S1 C14 106.59(10) . . ?
C7 N1 C10 108.27(17) . . ?
C7 N1 C4 126.20(18) . . ?
C10 N1 C4 125.40(18) . . ?
C13 N2 C12 113.20(17) . . ?
C13 N2 S1 115.11(14) . . ?
C12 N2 S1 115.50(14) . . ?
C2 C1 C6 119.9(2) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C1 C2 C3 119.9(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 N1 119.7(2) . . ?
C5 C4 N1 120.29(19) . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C8 C7 N1 108.53(19) . . ?
C8 C7 H7 125.7 . . ?
N1 C7 H7 125.7 . . ?
C7 C8 C9 107.25(19) . . ?
C7 C8 H8 126.4 . . ?
C9 C8 H8 126.4 . . ?
C10 C9 C8 107.84(19) . . ?
C10 C9 C13 121.91(19) . . ?
C8 C9 C13 130.2(2) . . ?
C9 C10 N1 108.10(19) . . ?
C9 C10 C11 125.66(19) . . ?
N1 C10 C11 126.11(18) . . ?
C10 C11 C12 107.50(18) . . ?
C10 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
C10 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
N2 C12 C11 109.74(17) . . ?
N2 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
N2 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
N2 C13 C9 108.54(17) . . ?
N2 C13 H13A 110.0 . . ?
C9 C13 H13A 110.0 . . ?
N2 C13 H13B 110.0 . . ?
C9 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
C19 C14 C15 120.56(19) . . ?
C19 C14 S1 119.36(17) . . ?
C15 C14 S1 119.95(16) . . ?
C16 C15 C14 119.3(2) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 121.3(2) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 118.2(2) . . ?
C18 C17 C20 120.7(2) . . ?
C16 C17 C20 121.1(2) . . ?
C19 C18 C17 121.4(2) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C14 119.2(2) . . ?
C18 C19 H19 120.4 . . ?
C14 C19 H19 120.4 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
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
S1 O2 1.4301(17) . ?
S1 O3 1.4367(16) . ?
S1 N2 1.6415(18) . ?
S1 C14 1.765(2) . ?
N1 C7 1.375(3) . ?
N1 C10 1.382(3) . ?
N1 C4 1.432(3) . ?
N2 C13 1.482(3) . ?
N2 C12 1.486(3) . ?
C1 C2 1.383(4) . ?
C1 C6 1.389(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(3) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.369(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.410(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.366(3) . ?
C9 C13 1.501(3) . ?
C10 C11 1.485(3) . ?
C11 C12 1.525(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C19 1.388(3) . ?
C14 C15 1.388(3) . ?
C15 C16 1.383(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.395(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(3) . ?
C17 C20 1.506(3) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N2 C13 -175.64(14) . . . . ?
O3 S1 N2 C13 -46.51(17) . . . . ?
C14 S1 N2 C13 68.79(17) . . . . ?
O2 S1 N2 C12 49.49(17) . . . . ?
O3 S1 N2 C12 178.62(14) . . . . ?
C14 S1 N2 C12 -66.08(17) . . . . ?
C6 C1 C2 C3 1.4(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C2 C3 C4 N1 -180.0(2) . . . . ?
C7 N1 C4 C3 61.1(3) . . . . ?
C10 N1 C4 C3 -114.4(2) . . . . ?
C7 N1 C4 C5 -118.5(2) . . . . ?
C10 N1 C4 C5 66.0(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
N1 C4 C5 C6 -179.9(2) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C2 C1 C6 C5 -1.3(4) . . . . ?
C10 N1 C7 C8 -0.8(2) . . . . ?
C4 N1 C7 C8 -176.9(2) . . . . ?
N1 C7 C8 C9 0.7(2) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C7 C8 C9 C13 179.8(2) . . . . ?
C8 C9 C10 N1 -0.1(2) . . . . ?
C13 C9 C10 N1 179.76(19) . . . . ?
C8 C9 C10 C11 175.9(2) . . . . ?
C13 C9 C10 C11 -4.2(3) . . . . ?
C7 N1 C10 C9 0.5(2) . . . . ?
C4 N1 C10 C9 176.65(19) . . . . ?
C7 N1 C10 C11 -175.5(2) . . . . ?
C4 N1 C10 C11 0.7(3) . . . . ?
C9 C10 C11 C12 19.8(3) . . . . ?
N1 C10 C11 C12 -164.9(2) . . . . ?
C13 N2 C12 C11 68.6(2) . . . . ?
S1 N2 C12 C11 -155.73(15) . . . . ?
C10 C11 C12 N2 -48.8(2) . . . . ?
C12 N2 C13 C9 -49.1(2) . . . . ?
S1 N2 C13 C9 175.04(14) . . . . ?
C10 C9 C13 N2 17.4(3) . . . . ?
C8 C9 C13 N2 -162.9(2) . . . . ?
O2 S1 C14 C19 -30.26(19) . . . . ?
O3 S1 C14 C19 -160.84(16) . . . . ?
N2 S1 C14 C19 84.47(18) . . . . ?
O2 S1 C14 C15 153.75(17) . . . . ?
O3 S1 C14 C15 23.2(2) . . . . ?
N2 S1 C14 C15 -91.52(18) . . . . ?
C19 C14 C15 C16 -0.2(3) . . . . ?
S1 C14 C15 C16 175.76(16) . . . . ?
C14 C15 C16 C17 0.8(3) . . . . ?
C15 C16 C17 C18 -1.0(3) . . . . ?
C15 C16 C17 C20 179.4(2) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C20 C17 C18 C19 -179.9(2) . . . . ?
C17 C18 C19 C14 0.0(3) . . . . ?
C15 C14 C19 C18 -0.2(3) . . . . ?
S1 C14 C19 C18 -176.20(15) . . . . ?
