#------------------------------------------------------------------------------
#$Date: 2020-02-29 02:19:51 +0200 (Sat, 29 Feb 2020) $
#$Revision: 248550 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/79/4037995.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_4037995
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 H19 N O4 S'
_chemical_formula_weight         381.43
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   15.3107(7)
_cell_length_b                   7.6551(3)
_cell_length_c                   33.1427(13)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      26.26
_cell_measurement_theta_min      2.66
_cell_volume                     3884.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      301(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0150
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            29746
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.193
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0441
_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)+(0.0523P)²+2.0623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1167
_reflns_number_gt                3021
_reflns_number_total             3398
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b03281_si_002.cif
_cod_data_source_block           Compound9aa
_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/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4037995
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'
'-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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.53309(3) 1.19771(6) 0.606241(15) 0.03973(17) Uani 1 1 d . . .
O4 O 0.60982(10) 1.3033(2) 0.60930(5) 0.0570(4) Uani 1 1 d . . .
C6 C 0.50339(11) 0.8509(2) 0.63087(5) 0.0333(4) Uani 1 1 d . . .
O3 O 0.45601(9) 1.2471(2) 0.62772(5) 0.0556(4) Uani 1 1 d . . .
C12 C 0.34038(12) 0.8496(3) 0.64748(5) 0.0385(4) Uani 1 1 d . . .
C1 C 0.56373(11) 0.9853(2) 0.62320(5) 0.0328(4) Uani 1 1 d . . .
C7 C 0.40909(12) 0.8594(2) 0.61912(5) 0.0356(4) Uani 1 1 d . . .
C8 C 0.38873(12) 0.8621(3) 0.57830(6) 0.0401(4) Uani 1 1 d . . .
H8 H 0.4339 0.8614 0.5596 0.048 Uiso 1 1 calc R . .
C10 C 0.23555(13) 0.8607(3) 0.59258(6) 0.0504(5) Uani 1 1 d . . .
H10 H 0.1777 0.8648 0.5840 0.061 Uiso 1 1 calc R . .
C5 C 0.53529(13) 0.6988(3) 0.64802(6) 0.0443(5) Uani 1 1 d . . .
H5 H 0.4969 0.6074 0.6533 0.053 Uiso 1 1 calc R . .
C13 C 0.35737(12) 0.8338(3) 0.69153(5) 0.0410(5) Uani 1 1 d . . .
C2 C 0.65167(12) 0.9627(3) 0.63209(6) 0.0442(5) Uani 1 1 d . . .
H2 H 0.6912 1.0514 0.6262 0.053 Uiso 1 1 calc R . .
C9 C 0.30297(12) 0.8656(3) 0.56451(6) 0.0432(5) Uani 1 1 d . . .
C11 C 0.25475(13) 0.8498(3) 0.63317(6) 0.0479(5) Uani 1 1 d . . .
H11 H 0.2091 0.8423 0.6516 0.057 Uiso 1 1 calc R . .
O2 O 0.20557(11) 0.8669(3) 0.51024(4) 0.0747(6) Uani 1 1 d . . .
C19 C 0.28872(14) 0.8775(3) 0.52034(6) 0.0531(6) Uani 1 1 d . . .
N1 N 0.50778(17) 1.1938(3) 0.55915(6) 0.0575(5) Uani 1 1 d . . .
C3 C 0.68082(14) 0.8107(3) 0.64943(7) 0.0531(6) Uani 1 1 d . . .
H3 H 0.7397 0.7970 0.6556 0.064 Uiso 1 1 calc R . .
C14 C 0.41448(14) 0.9442(3) 0.71154(6) 0.0499(5) Uani 1 1 d . . .
H14 H 0.4414 1.0349 0.6976 0.060 Uiso 1 1 calc R . .
O1 O 0.34636(11) 0.8945(3) 0.49591(5) 0.0794(6) Uani 1 1 d . . .
C4 C 0.62261(15) 0.6788(3) 0.65755(7) 0.0533(6) Uani 1 1 d . . .
H4 H 0.6420 0.5759 0.6695 0.064 Uiso 1 1 calc R . .
C18 C 0.3922(2) 0.7879(4) 0.77323(7) 0.0751(8) Uani 1 1 d . . .
H18 H 0.4048 0.7711 0.8004 0.090 Uiso 1 1 calc R . .
C17 C 0.31649(17) 0.7031(3) 0.71352(7) 0.0609(6) Uani 1 1 d . . .
H17 H 0.2767 0.6297 0.7008 0.073 Uiso 1 1 calc R . .
C21 C 0.0926(2) 0.8475(5) 0.46302(8) 0.0868(10) Uani 1 1 d . . .
H21A H 0.0809 0.7301 0.4716 0.130 Uiso 1 1 calc R . .
H21B H 0.0763 0.8605 0.4352 0.130 Uiso 1 1 calc R . .
H21C H 0.0594 0.9276 0.4792 0.130 Uiso 1 1 calc R . .
C15 C 0.43183(17) 0.9206(4) 0.75220(7) 0.0661(7) Uani 1 1 d . . .
H15 H 0.4705 0.9950 0.7653 0.079 Uiso 1 1 calc R . .
C20 C 0.18361(19) 0.8838(5) 0.46750(7) 0.0813(9) Uani 1 1 d . . .
H20A H 0.1964 1.0012 0.4582 0.098 Uiso 1 1 calc R . .
H20B H 0.2178 0.8021 0.4516 0.098 Uiso 1 1 calc R . .
C16 C 0.3342(2) 0.6806(4) 0.75412(8) 0.0770(8) Uani 1 1 d . . .
H16 H 0.3065 0.5921 0.7685 0.092 Uiso 1 1 calc R . .
H1A H 0.5507(19) 1.162(4) 0.5449(8) 0.069(9) Uiso 1 1 d . . .
H1B H 0.4610(18) 1.153(4) 0.5550(8) 0.063(8) Uiso 1 1 d . . .
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'
O O 0.0106 0.0060 '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'
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
O3 S1 O4 119.60(10) . . ?
O3 S1 N1 106.83(12) . . ?
O4 S1 N1 106.10(11) . . ?
O3 S1 C1 107.53(9) . . ?
O4 S1 C1 106.08(9) . . ?
N1 S1 C1 110.61(10) . . ?
C5 C6 C1 117.24(17) . . ?
C5 C6 C7 118.91(17) . . ?
C1 C6 C7 123.72(17) . . ?
C11 C12 C7 118.28(17) . . ?
C11 C12 C13 119.89(16) . . ?
C7 C12 C13 121.80(17) . . ?
C2 C1 C6 120.51(18) . . ?
C2 C1 S1 115.80(15) . . ?
C6 C1 S1 123.46(14) . . ?
C8 C7 C12 118.80(17) . . ?
C8 C7 C6 118.08(16) . . ?
C12 C7 C6 122.89(16) . . ?
C7 C8 C9 122.18(17) . . ?
C11 C10 C9 119.73(18) . . ?
C4 C5 C6 121.8(2) . . ?
C14 C13 C17 118.26(19) . . ?
C14 C13 C12 122.02(18) . . ?
C17 C13 C12 119.71(18) . . ?
C3 C2 C1 120.64(19) . . ?
C10 C9 C8 118.73(18) . . ?
C10 C9 C19 123.58(18) . . ?
C8 C9 C19 117.69(18) . . ?
C10 C11 C12 122.16(18) . . ?
C19 O2 C20 117.56(19) . . ?
O1 C19 O2 122.9(2) . . ?
O1 C19 C9 124.2(2) . . ?
O2 C19 C9 112.89(18) . . ?
C2 C3 C4 119.61(19) . . ?
C15 C14 C13 120.5(2) . . ?
C3 C4 C5 120.1(2) . . ?
C16 C18 C15 119.8(2) . . ?
C16 C17 C13 120.9(2) . . ?
C18 C15 C14 120.4(2) . . ?
C21 C20 O2 107.9(2) . . ?
C18 C16 C17 120.2(3) . . ?
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 O3 1.4291(15) . ?
S1 O4 1.4294(16) . ?
S1 N1 1.609(2) . ?
S1 C1 1.7835(19) . ?
C6 C5 1.385(3) . ?
C6 C1 1.406(3) . ?
C6 C7 1.497(3) . ?
C12 C11 1.394(3) . ?
C12 C7 1.413(3) . ?
C12 C13 1.488(3) . ?
C1 C2 1.389(3) . ?
C7 C8 1.389(3) . ?
C8 C9 1.391(3) . ?
C10 C11 1.379(3) . ?
C10 C9 1.390(3) . ?
C5 C4 1.382(3) . ?
C13 C14 1.385(3) . ?
C13 C17 1.387(3) . ?
C2 C3 1.372(3) . ?
C9 C19 1.483(3) . ?
O2 C19 1.319(3) . ?
O2 C20 1.461(3) . ?
C19 O1 1.205(3) . ?
C3 C4 1.373(3) . ?
C14 C15 1.385(3) . ?
C18 C16 1.366(4) . ?
C18 C15 1.373(4) . ?
C17 C16 1.383(4) . ?
C21 C20 1.429(4) . ?
