#------------------------------------------------------------------------------
#$Date: 2025-03-04 21:28:57 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298155 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/37/1573780.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_1573780
loop_
_publ_author_name
'Erchinger, Johannes E.'
'Lenz, Madina'
'Mukherjee, Poulami'
'Li, Yan-Bo'
'Suresh, Adhya'
'Daniliuc, Constantin G.'
'Gutierrez, Osvaldo'
'Glorius, Frank'
_publ_section_title
;
 Mechanistic insights into the regiodivergent insertion of
 bicyclo[1.1.0]butanes towards carbocycle-tethered N-heteroarenes.
;
_journal_issue                   9
_journal_name_full               'Chemical science'
_journal_page_first              4006
_journal_page_last               4013
_journal_paper_doi               10.1039/d4sc08637f
_journal_volume                  16
_journal_year                    2025
_chemical_formula_sum            'C17 H18 N2 O2 S'
_chemical_formula_weight         314.39
_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
_atom_sites_solution_primary     direct
_audit_creation_method           'APEX4 v2022.10-1'
_audit_update_record
;
2024-07-10 deposited with the CCDC.	2025-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                102.5420(10)
_cell_angle_beta                 99.9030(10)
_cell_angle_gamma                102.1910(10)
_cell_formula_units_Z            2
_cell_length_a                   6.00840(10)
_cell_length_b                   9.2515(2)
_cell_length_c                   15.0308(3)
_cell_measurement_reflns_used    7285
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      66.6776
_cell_measurement_theta_min      5.1989
_cell_volume                     776.13(3)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker APEX4 v2022.10-1 Photon III'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'SHELXT 2011/1 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2018)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11242
_diffrn_reflns_theta_full        66.67
_diffrn_reflns_theta_max         66.67
_diffrn_reflns_theta_min         3.09
_diffrn_source                   'Cu ImS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'micro focus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.923
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.279
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0336
_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)+(0.0397P)²+0.4619P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0875
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2468
_reflns_number_total             2710
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc08637f2.cif
_cod_data_source_block           glo10593_4aj-major_regioisomer
_cod_depositor_comments
'Adding full bibliography for 1573780--1573782.cif.'
_cod_database_code               1573780
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.45845(7) 0.88648(4) 0.35811(3) 0.01803(13) Uani d . . . 1 . .
N N1 0.6588(2) 0.65525(15) 0.16869(10) 0.0174(3) Uani d . . . 1 . .
N N2 0.2979(2) 0.65118(16) 0.02161(9) 0.0194(3) Uani d . . . 1 . .
O O1 0.47011(19) 0.69424(13) 0.53400(8) 0.0200(3) Uani d . . . 1 . .
O O2 0.10958(19) 0.70655(13) 0.47073(8) 0.0188(3) Uani d . . . 1 . .
C C1 0.3696(3) 0.69251(17) 0.37103(11) 0.0147(3) Uani d . . . 1 . .
C C2 0.1796(3) 0.57984(17) 0.28791(10) 0.0142(3) Uani d . . . 1 . .
H H2A 0.089135 0.630839 0.248924 0.017000 Uiso calc U . R 1 . .
H H2B 0.074242 0.499104 0.306010 0.017000 Uiso calc U . R 1 . .
C C3 0.3769(3) 0.52515(17) 0.24551(10) 0.0132(3) Uani d . . . 1 . .
C C4 0.5496(3) 0.60441(18) 0.34219(10) 0.0147(3) Uani d . . . 1 . .
H H4A 0.580073 0.532745 0.380237 0.018000 Uiso calc U . R 1 . .
H H4B 0.697766 0.671420 0.338333 0.018000 Uiso calc U . R 1 . .
C C5 0.3287(3) 0.69815(17) 0.46794(11) 0.0149(3) Uani d . . . 1 . .
C C6 0.0515(3) 0.7139(2) 0.56086(11) 0.0220(4) Uani d . . . 1 . .
H H6A 0.080081 0.625276 0.582246 0.033000 Uiso calc U . R 1 . .
H H6B -0.113736 0.713025 0.555126 0.033000 Uiso calc U . R 1 . .
H H6C 0.148968 0.808482 0.606238 0.033000 Uiso calc U . R 1 . .
C C7 0.1960(3) 0.9523(2) 0.35926(13) 0.0232(4) Uani d . . . 1 . .
H H7A 0.064190 0.876869 0.313309 0.035000 Uiso calc U . R 1 . .
H H7B 0.218121 1.050808 0.343314 0.035000 Uiso calc U . R 1 . .
H H7C 0.163442 0.964894 0.421786 0.035000 Uiso calc U . R 1 . .
C C8 0.4348(3) 0.59718(16) 0.16753(11) 0.0129(3) Uani d . . . 1 . .
C C9 0.2572(3) 0.59406(17) 0.09304(11) 0.0160(3) Uani d . . . 1 . .
H H9 0.099957 0.549051 0.093401 0.019000 Uiso calc U . R 1 . .
C C10 0.5229(3) 0.71263(18) 0.02486(11) 0.0188(3) Uani d . . . 1 . .
H H10 0.561820 0.757224 -0.023556 0.023000 Uiso calc U . R 1 . .
C C11 0.6995(3) 0.71264(18) 0.09688(12) 0.0194(4) Uani d . . . 1 . .
H H11 0.856775 0.755240 0.095464 0.023000 Uiso calc U . R 1 . .
C C21 0.3368(3) 0.35318(17) 0.20967(10) 0.0141(3) Uani d . . . 1 . .
C C22 0.1177(3) 0.26110(19) 0.15815(11) 0.0182(3) Uani d . . . 1 . .
H H22 -0.010012 0.305671 0.148106 0.022000 Uiso calc U . R 1 . .
C C23 0.0849(3) 0.10506(19) 0.12149(12) 0.0228(4) Uani d . . . 1 . .
H H23 -0.064854 0.043547 0.086289 0.027000 Uiso calc U . R 1 . .
C C24 0.2700(3) 0.03817(19) 0.13597(12) 0.0233(4) Uani d . . . 1 . .
H H24 0.246978 -0.068797 0.110966 0.028000 Uiso calc U . R 1 . .
C C25 0.4882(3) 0.12847(19) 0.18710(12) 0.0211(4) Uani d . . . 1 . .
H H25 0.615317 0.083398 0.197317 0.025000 Uiso calc U . R 1 . .
C C26 0.5212(3) 0.28474(18) 0.22340(11) 0.0171(3) Uani d . . . 1 . .
H H26 0.671563 0.345971 0.258099 0.021000 Uiso calc U . R 1 . .
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'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 S1 C1 . . 103.00(8) ?
C8 N1 C11 . . 116.22(14) ?
C9 N2 C10 . . 115.68(14) ?
C5 O2 C6 . . 115.36(12) ?
C5 C1 C2 . . 116.92(12) ?
C5 C1 C4 . . 115.85(13) ?
C2 C1 C4 . . 89.39(11) ?
C5 C1 S1 . . 109.97(10) ?
C2 C1 S1 . . 114.46(11) ?
C4 C1 S1 . . 108.76(10) ?
C1 C2 C3 . . 88.97(11) ?
C1 C2 H2A . . 113.800000 ?
C3 C2 H2A . . 113.800000 ?
C1 C2 H2B . . 113.800000 ?
C3 C2 H2B . . 113.800000 ?
H2A C2 H2B . . 111.000000 ?
C21 C3 C8 . . 107.76(12) ?
C21 C3 C4 . . 116.92(12) ?
C8 C3 C4 . . 113.74(12) ?
C21 C3 C2 . . 116.02(12) ?
C8 C3 C2 . . 113.10(12) ?
C4 C3 C2 . . 88.57(11) ?
C1 C4 C3 . . 89.06(11) ?
C1 C4 H4A . . 113.800000 ?
C3 C4 H4A . . 113.800000 ?
C1 C4 H4B . . 113.800000 ?
C3 C4 H4B . . 113.800000 ?
H4A C4 H4B . . 111.000000 ?
O1 C5 O2 . . 123.93(14) ?
O1 C5 C1 . . 125.45(14) ?
O2 C5 C1 . . 110.62(13) ?
O2 C6 H6A . . 109.500000 ?
O2 C6 H6B . . 109.500000 ?
H6A C6 H6B . . 109.500000 ?
O2 C6 H6C . . 109.500000 ?
H6A C6 H6C . . 109.500000 ?
H6B C6 H6C . . 109.500000 ?
S1 C7 H7A . . 109.500000 ?
S1 C7 H7B . . 109.500000 ?
H7A C7 H7B . . 109.500000 ?
S1 C7 H7C . . 109.500000 ?
H7A C7 H7C . . 109.500000 ?
H7B C7 H7C . . 109.500000 ?
N1 C8 C9 . . 120.55(14) ?
N1 C8 C3 . . 118.86(13) ?
C9 C8 C3 . . 120.48(13) ?
N2 C9 C8 . . 123.14(14) ?
N2 C9 H9 . . 118.400000 ?
C8 C9 H9 . . 118.400000 ?
N2 C10 C11 . . 121.50(15) ?
N2 C10 H10 . . 119.200000 ?
C11 C10 H10 . . 119.200000 ?
N1 C11 C10 . . 122.86(14) ?
N1 C11 H11 . . 118.600000 ?
C10 C11 H11 . . 118.600000 ?
C26 C21 C22 . . 118.53(14) ?
C26 C21 C3 . . 120.63(14) ?
C22 C21 C3 . . 120.76(14) ?
C23 C22 C21 . . 120.54(15) ?
C23 C22 H22 . . 119.700000 ?
C21 C22 H22 . . 119.700000 ?
C22 C23 C24 . . 120.35(16) ?
C22 C23 H23 . . 119.800000 ?
C24 C23 H23 . . 119.800000 ?
C25 C24 C23 . . 119.60(15) ?
C25 C24 H24 . . 120.200000 ?
C23 C24 H24 . . 120.200000 ?
C24 C25 C26 . . 120.02(16) ?
C24 C25 H25 . . 120.000000 ?
C26 C25 H25 . . 120.000000 ?
C25 C26 C21 . . 120.95(15) ?
C25 C26 H26 . . 119.500000 ?
C21 C26 H26 . . 119.500000 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C7 . 1.8077(17) ?
S1 C1 . 1.8235(15) ?
N1 C8 . 1.335(2) ?
N1 C11 . 1.338(2) ?
N2 C9 . 1.332(2) ?
N2 C10 . 1.339(2) ?
O1 C5 . 1.2031(19) ?
O2 C5 . 1.3424(19) ?
O2 C6 . 1.4469(19) ?
C1 C5 . 1.510(2) ?
C1 C2 . 1.547(2) ?
C1 C4 . 1.550(2) ?
C2 C3 . 1.562(2) ?
C2 H2A . 0.990000 ?
C2 H2B . 0.990000 ?
C3 C21 . 1.517(2) ?
C3 C8 . 1.523(2) ?
C3 C4 . 1.557(2) ?
C4 H4A . 0.990000 ?
C4 H4B . 0.990000 ?
C6 H6A . 0.980000 ?
C6 H6B . 0.980000 ?
C6 H6C . 0.980000 ?
C7 H7A . 0.980000 ?
C7 H7B . 0.980000 ?
C7 H7C . 0.980000 ?
C8 C9 . 1.398(2) ?
C9 H9 . 0.950000 ?
C10 C11 . 1.379(2) ?
C10 H10 . 0.950000 ?
C11 H11 . 0.950000 ?
C21 C26 . 1.395(2) ?
C21 C22 . 1.396(2) ?
C22 C23 . 1.387(2) ?
C22 H22 . 0.950000 ?
C23 C24 . 1.390(3) ?
C23 H23 . 0.950000 ?
C24 C25 . 1.386(3) ?
C24 H24 . 0.950000 ?
C25 C26 . 1.388(2) ?
C25 H25 . 0.950000 ?
C26 H26 . 0.950000 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C6 H6B O1 1_455 0.98 2.43 3.408(2) 176.3 ?
C7 H7C O2 . 0.98 2.62 3.115(2) 111.3 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 S1 C1 C5 . . . . -68.74(12) ?
C7 S1 C1 C2 . . . . 65.25(12) ?
C7 S1 C1 C4 . . . . 163.42(11) ?
C5 C1 C2 C3 . . . . -134.02(13) ?
C4 C1 C2 C3 . . . . -15.09(11) ?
S1 C1 C2 C3 . . . . 95.31(11) ?
C1 C2 C3 C21 . . . . 134.48(13) ?
C1 C2 C3 C8 . . . . -100.26(13) ?
C1 C2 C3 C4 . . . . 15.02(11) ?
C5 C1 C4 C3 . . . . 135.01(13) ?
C2 C1 C4 C3 . . . . 15.14(11) ?
S1 C1 C4 C3 . . . . -100.56(11) ?
C21 C3 C4 C1 . . . . -133.64(13) ?
C8 C3 C4 C1 . . . . 99.70(13) ?
C2 C3 C4 C1 . . . . -14.99(11) ?
C6 O2 C5 O1 . . . . 1.2(2) ?
C6 O2 C5 C1 . . . . -179.48(12) ?
C2 C1 C5 O1 . . . . 132.52(16) ?
C4 C1 C5 O1 . . . . 29.1(2) ?
S1 C1 C5 O1 . . . . -94.75(17) ?
C2 C1 C5 O2 . . . . -46.79(18) ?
C4 C1 C5 O2 . . . . -150.26(13) ?
S1 C1 C5 O2 . . . . 85.94(13) ?
C11 N1 C8 C9 . . . . 1.8(2) ?
C11 N1 C8 C3 . . . . 177.96(13) ?
C21 C3 C8 N1 . . . . -97.35(15) ?
C4 C3 C8 N1 . . . . 33.96(18) ?
C2 C3 C8 N1 . . . . 133.05(14) ?
C21 C3 C8 C9 . . . . 78.78(17) ?
C4 C3 C8 C9 . . . . -149.90(14) ?
C2 C3 C8 C9 . . . . -50.82(18) ?
C10 N2 C9 C8 . . . . 0.2(2) ?
N1 C8 C9 N2 . . . . -1.9(2) ?
C3 C8 C9 N2 . . . . -178.01(14) ?
C9 N2 C10 C11 . . . . 1.5(2) ?
C8 N1 C11 C10 . . . . -0.2(2) ?
N2 C10 C11 N1 . . . . -1.5(3) ?
C8 C3 C21 C26 . . . . 91.23(16) ?
C4 C3 C21 C26 . . . . -38.3(2) ?
C2 C3 C21 C26 . . . . -140.84(14) ?
C8 C3 C21 C22 . . . . -85.47(17) ?
C4 C3 C21 C22 . . . . 144.99(14) ?
C2 C3 C21 C22 . . . . 42.5(2) ?
C26 C21 C22 C23 . . . . 0.0(2) ?
C3 C21 C22 C23 . . . . 176.72(15) ?
C21 C22 C23 C24 . . . . 0.3(3) ?
C22 C23 C24 C25 . . . . -0.2(3) ?
C23 C24 C25 C26 . . . . -0.1(3) ?
C24 C25 C26 C21 . . . . 0.3(2) ?
C22 C21 C26 C25 . . . . -0.3(2) ?
C3 C21 C26 C25 . . . . -177.03(14) ?
