#------------------------------------------------------------------------------
#$Date: 2020-02-29 02:19:51 +0200 (Sat, 29 Feb 2020) $
#$Revision: 248550 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/79/4037991.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_4037991
loop_
_publ_author_name
'Arupula, Sanjeeva K.'
'Qureshi, Asif Ali'
'Swamy, K. C. Kumara'
_publ_section_title
;
 Lewis Base Switched [3+3] and [4+2] Annulation Reaction of δ-Acetoxy
 Allenoates with Cyclic N-Sulfonyl Imines: Divergent Synthesis of
 Functionalized α-Pyridyl Acetates and Teraryl Scaffolds.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03281
_journal_year                    2020
_chemical_formula_sum            'C21 H18 Br N O5 S'
_chemical_formula_weight         476.33
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.9477(14)
_cell_angle_beta                 105.4986(14)
_cell_angle_gamma                97.6309(14)
_cell_formula_units_Z            4
_cell_length_a                   11.45660(18)
_cell_length_b                   13.1897(2)
_cell_length_c                   14.5799(2)
_cell_measurement_reflns_used    13776
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.1160
_cell_measurement_theta_min      2.0180
_cell_volume                     2098.67(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω 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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33737
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    2.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needles
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         7387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0392P)²+2.2084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1143
_reflns_number_gt                5018
_reflns_number_total             7387
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b03281_si_002.cif
_cod_data_source_block           Compound4ca
_cod_original_cell_volume        2098.66(6)
_cod_database_code               4037991
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.13265(4) 0.74363(4) 0.06765(4) 0.0888(2) Uani 1 1 d . . .
Br2 Br -0.16130(5) 0.14393(4) 0.62478(4) 0.0897(2) Uani 1 1 d . . .
S2 S 0.00028(10) 0.67969(8) 0.68499(8) 0.0570(3) Uani 1 1 d . . .
S1 S 0.61396(10) 1.15836(8) 0.20092(8) 0.0594(3) Uani 1 1 d . . .
O1 O 0.6006(2) 1.04216(19) 0.15874(19) 0.0568(7) Uani 1 1 d . . .
O6 O 0.0666(2) 0.58754(19) 0.65825(17) 0.0513(6) Uani 1 1 d . . .
O9 O 0.1141(3) 0.4410(2) 1.08856(19) 0.0701(8) Uani 1 1 d . . .
O5 O 0.7230(3) 0.9061(2) 0.6274(2) 0.0754(9) Uani 1 1 d . . .
C4 C 0.2785(4) 0.8401(3) 0.0999(3) 0.0624(11) Uani 1 1 d . . .
C22 C 0.0100(3) 0.4855(3) 0.6537(3) 0.0456(9) Uani 1 1 d . . .
C34 C 0.3069(3) 0.4917(3) 0.7109(3) 0.0455(9) Uani 1 1 d . . .
C29 C 0.1399(3) 0.4604(3) 0.9015(3) 0.0478(9) Uani 1 1 d . . .
H29 H 0.0632 0.4334 0.9071 0.057 Uiso 1 1 calc R . .
C32 C 0.3657(3) 0.5407(3) 0.8851(3) 0.0540(10) Uani 1 1 d . . .
H32 H 0.4421 0.5694 0.8798 0.065 Uiso 1 1 calc R . .
C26 C 0.0009(3) 0.3219(3) 0.7171(3) 0.0519(10) Uani 1 1 d . . .
H26 H 0.0271 0.2790 0.7653 0.062 Uiso 1 1 calc R . .
C28 C 0.1592(3) 0.4626(3) 0.8116(3) 0.0433(9) Uani 1 1 d . . .
C6 C 0.4807(3) 0.8977(3) 0.2023(3) 0.0510(10) Uani 1 1 d . . .
C30 C 0.2323(3) 0.4975(3) 0.9834(3) 0.0477(9) Uani 1 1 d . . .
C13 C 0.7294(4) 0.8567(3) 0.1921(3) 0.0571(10) Uani 1 1 d . . .
O8 O 0.0622(3) 0.7655(2) 0.6534(2) 0.0763(9) Uani 1 1 d . . .
O3 O 0.7100(3) 1.2077(2) 0.1680(2) 0.0772(9) Uani 1 1 d . . .
O7 O -0.1280(2) 0.6511(2) 0.6491(2) 0.0707(8) Uani 1 1 d . . .
C27 C 0.0555(3) 0.4240(3) 0.7265(3) 0.0445(9) Uani 1 1 d . . .
C33 C 0.2765(3) 0.4999(3) 0.8033(3) 0.0446(9) Uani 1 1 d . . .
C2 C 0.3950(4) 0.9877(3) 0.0641(3) 0.0576(10) Uani 1 1 d . . .
H2 H 0.4031 1.0419 0.0260 0.069 Uiso 1 1 calc R . .
O2 O 0.4969(3) 1.1898(2) 0.1758(2) 0.0707(8) Uani 1 1 d . . .
C31 C 0.3451(4) 0.5405(3) 0.9737(3) 0.0567(10) Uani 1 1 d . . .
H31 H 0.4069 0.5691 1.0272 0.068 Uiso 1 1 calc R . .
C8 C 0.5600(4) 0.8920(3) 0.3785(3) 0.0570(11) Uani 1 1 d . . .
H8 H 0.4807 0.8951 0.3822 0.068 Uiso 1 1 calc R . .
O4 O 0.5206(3) 0.8804(3) 0.5643(2) 0.0898(10) Uani 1 1 d . . .
C40 C 0.2080(4) 0.4838(3) 1.0772(3) 0.0608(11) Uani 1 1 d . B .
N2 N 0.0319(4) 0.6921(3) 0.7973(3) 0.0656(11) Uani 1 1 d . . .
H43A H -0.006(4) 0.655(3) 0.824(3) 0.060(15) Uiso 1 1 d . . .
H43B H 0.110(4) 0.710(3) 0.830(3) 0.081(16) Uiso 1 1 d . . .
C25 C -0.0920(4) 0.2840(3) 0.6367(3) 0.0578(11) Uani 1 1 d . . .
N1 N 0.6578(6) 1.1586(4) 0.3126(3) 0.0749(13) Uani 1 1 d . . .
H22A H 0.719(4) 1.154(3) 0.332(3) 0.040(15) Uiso 1 1 d . . .
H22B H 0.608(5) 1.136(4) 0.344(4) 0.09(2) Uiso 1 1 d . . .
C1 C 0.4886(3) 0.9762(3) 0.1426(3) 0.0501(10) Uani 1 1 d . . .
C7 C 0.5823(4) 0.8879(3) 0.2895(3) 0.0528(10) Uani 1 1 d . . .
C19 C 0.6224(5) 0.8918(3) 0.5548(3) 0.0655(12) Uani 1 1 d . . .
C39 C 0.2802(3) 0.3994(3) 0.6565(3) 0.0543(10) Uani 1 1 d . . .
H39 H 0.2424 0.3419 0.6782 0.065 Uiso 1 1 calc R . .
C3 C 0.2892(4) 0.9186(3) 0.0423(3) 0.0616(11) Uani 1 1 d . . .
H3 H 0.2253 0.9251 -0.0110 0.074 Uiso 1 1 calc R . .
C5 C 0.3714(4) 0.8296(3) 0.1796(3) 0.0593(11) Uani 1 1 d . . .
H5 H 0.3612 0.7768 0.2186 0.071 Uiso 1 1 calc R . .
C35 C 0.3659(3) 0.5754(3) 0.6774(3) 0.0574(10) Uani 1 1 d . . .
H35 H 0.3870 0.6380 0.7133 0.069 Uiso 1 1 calc R . .
C11 C 0.7934(4) 0.8821(3) 0.3689(3) 0.0635(11) Uani 1 1 d . . .
H11 H 0.8731 0.8794 0.3662 0.076 Uiso 1 1 calc R . .
C12 C 0.7011(4) 0.8783(3) 0.2840(3) 0.0528(10) Uani 1 1 d . . .
O10 O 0.3031(3) 0.5237(3) 1.1486(2) 0.1065(13) Uani 1 1 d . . .
C14 C 0.6578(4) 0.7792(3) 0.1270(3) 0.0665(12) Uani 1 1 d . . .
H14 H 0.5876 0.7447 0.1388 0.080 Uiso 1 1 calc R . .
C37 C 0.3647(4) 0.4748(4) 0.5384(3) 0.0675(12) Uani 1 1 d . . .
H37 H 0.3833 0.4693 0.4803 0.081 Uiso 1 1 calc R . .
C36 C 0.3935(4) 0.5666(4) 0.5912(3) 0.0667(12) Uani 1 1 d . . .
H36 H 0.4319 0.6234 0.5690 0.080 Uiso 1 1 calc R . .
C10 C 0.7707(4) 0.8897(3) 0.4564(3) 0.0635(11) Uani 1 1 d . . .
H10 H 0.8347 0.8935 0.5119 0.076 Uiso 1 1 calc R . .
C38 C 0.3084(4) 0.3908(4) 0.5708(3) 0.0660(12) Uani 1 1 d . . .
H38 H 0.2894 0.3282 0.5350 0.079 Uiso 1 1 calc R . .
C23 C -0.0829(3) 0.4470(3) 0.5740(3) 0.0558(10) Uani 1 1 d . . .
H23 H -0.1115 0.4899 0.5263 0.067 Uiso 1 1 calc R . .
C9 C 0.6523(4) 0.8917(3) 0.4618(3) 0.0559(10) Uani 1 1 d . . .
C18 C 0.8333(4) 0.9078(4) 0.1734(3) 0.0698(12) Uani 1 1 d . . .
H18 H 0.8827 0.9603 0.2161 0.084 Uiso 1 1 calc R . .
C24 C -0.1333(4) 0.3454(3) 0.5647(3) 0.0617(11) Uani 1 1 d . . .
H24 H -0.1947 0.3188 0.5102 0.074 Uiso 1 1 calc R . .
C17 C 0.8636(5) 0.8803(4) 0.0908(4) 0.0832(15) Uani 1 1 d . . .
H17 H 0.9332 0.9148 0.0780 0.100 Uiso 1 1 calc R . .
C15 C 0.6877(5) 0.7522(4) 0.0453(4) 0.0834(15) Uani 1 1 d . . .
H15 H 0.6381 0.7002 0.0022 0.100 Uiso 1 1 calc R . .
C16 C 0.7910(6) 0.8022(5) 0.0278(4) 0.0864(16) Uani 1 1 d . . .
H16 H 0.8124 0.7834 -0.0269 0.104 Uiso 1 1 calc R . .
C20 C 0.7081(5) 0.9029(4) 0.7227(3) 0.0907(16) Uani 1 1 d . . .
H20A H 0.6623 0.8376 0.7296 0.109 Uiso 1 1 calc R . .
H20B H 0.6637 0.9572 0.7350 0.109 Uiso 1 1 calc R . .
C21 C 0.8315(6) 0.9165(5) 0.7904(4) 0.117(2) Uani 1 1 d . . .
H21A H 0.8740 0.8617 0.7783 0.176 Uiso 1 1 calc R . .
H21B H 0.8244 0.9158 0.8545 0.176 Uiso 1 1 calc R . .
H21C H 0.8763 0.9809 0.7824 0.176 Uiso 1 1 calc R . .
C42 C 0.3536(10) 0.5867(8) 1.3013(6) 0.204(5) Uani 1 1 d . . .
H42A H 0.4344 0.6033 1.2935 0.306 Uiso 1 1 calc R A 1
H42B H 0.3593 0.5731 1.3664 0.306 Uiso 1 1 calc R A 1
H42C H 0.3094 0.6434 1.2847 0.306 Uiso 1 1 calc R A 1
C41A C 0.2927(8) 0.5007(9) 1.2422(4) 0.173(6) Uani 0.82 1 d P B 1
H41A H 0.2074 0.4882 1.2425 0.207 Uiso 1 1 calc R B 1
H41B H 0.3303 0.4406 1.2627 0.207 Uiso 1 1 calc R B 1
C41B C 0.3207(17) 0.3639(15) 1.2517(13) 0.041(5) Uani 0.18 1 d P C 2
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'
Br Br -0.2901 2.4595 '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
O8 S2 O7 121.29(19) . . ?
O8 S2 N2 108.6(2) . . ?
O7 S2 N2 107.8(2) . . ?
O8 S2 O6 102.57(16) . . ?
O7 S2 O6 108.66(16) . . ?
N2 S2 O6 107.11(18) . . ?
O3 S1 O2 120.97(19) . . ?
O3 S1 N1 109.1(3) . . ?
O2 S1 N1 108.0(3) . . ?
O3 S1 O1 102.41(17) . . ?
O2 S1 O1 108.34(16) . . ?
N1 S1 O1 107.2(2) . . ?
C1 O1 S1 120.5(2) . . ?
C22 O6 S2 119.9(2) . . ?
C19 O5 C20 117.7(4) . . ?
C3 C4 C5 121.2(4) . . ?
C3 C4 Br1 118.9(3) . . ?
C5 C4 Br1 119.9(3) . . ?
C23 C22 C27 121.7(4) . . ?
C23 C22 O6 119.2(3) . . ?
C27 C22 O6 119.0(3) . . ?
C39 C34 C35 117.7(4) . . ?
C39 C34 C33 120.8(3) . . ?
C35 C34 C33 121.4(3) . . ?
C28 C29 C30 121.8(3) . . ?
C31 C32 C33 122.2(4) . . ?
C25 C26 C27 120.5(4) . . ?
C29 C28 C33 119.1(3) . . ?
C29 C28 C27 119.1(3) . . ?
C33 C28 C27 121.8(3) . . ?
C1 C6 C5 116.8(4) . . ?
C1 C6 C7 122.0(3) . . ?
C5 C6 C7 121.1(4) . . ?
C31 C30 C29 118.6(3) . . ?
C31 C30 C40 122.9(4) . . ?
C29 C30 C40 118.4(3) . . ?
C14 C13 C18 118.6(4) . . ?
C14 C13 C12 120.4(4) . . ?
C18 C13 C12 120.7(4) . . ?
C22 C27 C26 117.3(3) . . ?
C22 C27 C28 122.8(3) . . ?
C26 C27 C28 119.9(3) . . ?
C32 C33 C28 118.2(3) . . ?
C32 C33 C34 120.2(3) . . ?
C28 C33 C34 121.5(3) . . ?
C3 C2 C1 119.4(4) . . ?
C32 C31 C30 119.9(4) . . ?
C9 C8 C7 121.9(4) . . ?
O9 C40 O10 123.2(4) . . ?
O9 C40 C30 124.8(4) . . ?
O10 C40 C30 111.9(4) . . ?
C24 C25 C26 121.1(4) . . ?
C24 C25 Br2 119.5(3) . . ?
C26 C25 Br2 119.4(3) . . ?
C2 C1 C6 122.6(4) . . ?
C2 C1 O1 118.5(4) . . ?
C6 C1 O1 118.7(4) . . ?
C8 C7 C12 118.9(4) . . ?
C8 C7 C6 119.3(4) . . ?
C12 C7 C6 121.7(4) . . ?
O4 C19 O5 123.6(4) . . ?
O4 C19 C9 125.0(5) . . ?
O5 C19 C9 111.5(4) . . ?
C38 C39 C34 121.3(4) . . ?
C4 C3 C2 119.4(4) . . ?
C4 C5 C6 120.5(4) . . ?
C36 C35 C34 120.7(4) . . ?
C10 C11 C12 122.2(4) . . ?
C11 C12 C7 118.0(4) . . ?
C11 C12 C13 119.1(4) . . ?
C7 C12 C13 122.7(4) . . ?
C40 O10 C41A 115.0(4) . . ?
C15 C14 C13 121.5(5) . . ?
C36 C37 C38 120.2(4) . . ?
C37 C36 C35 120.2(4) . . ?
C11 C10 C9 119.7(4) . . ?
C37 C38 C39 119.8(4) . . ?
C24 C23 C22 120.2(4) . . ?
C8 C9 C10 119.0(4) . . ?
C8 C9 C19 119.6(4) . . ?
C10 C9 C19 121.4(4) . . ?
C13 C18 C17 119.8(5) . . ?
C25 C24 C23 119.1(4) . . ?
C16 C17 C18 120.2(5) . . ?
C16 C15 C14 119.5(5) . . ?
C15 C16 C17 120.3(5) . . ?
O5 C20 C21 107.7(4) . . ?
C42 C41A O10 105.2(7) . . ?
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
Br1 C4 1.899(4) . ?
Br2 C25 1.894(4) . ?
S2 O8 1.412(3) . ?
S2 O7 1.416(3) . ?
S2 N2 1.577(4) . ?
S2 O6 1.606(3) . ?
S1 O3 1.407(3) . ?
S1 O2 1.414(3) . ?
S1 N1 1.570(5) . ?
S1 O1 1.604(3) . ?
O1 C1 1.409(4) . ?
O6 C22 1.406(4) . ?
O9 C40 1.201(5) . ?
O5 C19 1.327(5) . ?
O5 C20 1.445(5) . ?
C4 C3 1.369(6) . ?
C4 C5 1.374(6) . ?
C22 C23 1.377(5) . ?
C22 C27 1.390(5) . ?
C34 C39 1.384(5) . ?
C34 C35 1.389(5) . ?
C34 C33 1.483(5) . ?
C29 C28 1.387(5) . ?
C29 C30 1.390(5) . ?
C32 C31 1.374(5) . ?
C32 C33 1.383(5) . ?
C26 C25 1.382(5) . ?
C26 C27 1.392(5) . ?
C28 C33 1.406(5) . ?
C28 C27 1.490(5) . ?
C6 C1 1.384(5) . ?
C6 C5 1.394(5) . ?
C6 C7 1.499(5) . ?
C30 C31 1.385(5) . ?
C30 C40 1.479(5) . ?
C13 C14 1.383(6) . ?
C13 C18 1.385(6) . ?
C13 C12 1.487(5) . ?
C2 C3 1.372(5) . ?
C2 C1 1.372(5) . ?
C8 C9 1.381(6) . ?
C8 C7 1.389(5) . ?
O4 C19 1.201(5) . ?
C40 O10 1.323(5) . ?
C25 C24 1.370(6) . ?
C7 C12 1.407(5) . ?
C19 C9 1.485(6) . ?
C39 C38 1.375(5) . ?
C35 C36 1.380(5) . ?
C11 C10 1.371(5) . ?
C11 C12 1.391(6) . ?
O10 C41A 1.441(7) . ?
C14 C15 1.374(6) . ?
C37 C36 1.364(6) . ?
C37 C38 1.369(6) . ?
C10 C9 1.384(5) . ?
C23 C24 1.374(5) . ?
C18 C17 1.388(6) . ?
C17 C16 1.378(7) . ?
C15 C16 1.365(7) . ?
C20 C21 1.476(7) . ?
C42 C41A 1.385(11) . ?
