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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/59/1555926.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_1555926
loop_
_publ_author_name
'Siva Kumari, A. Leela'
'Siva Reddy, Alla'
'Swamy, K. C. Kumara'
_publ_section_title
;
 Transition Metal-Free Cascade Cyclization of Epoxy-Ynamides: To Go for
 1,3-Oxazines or 1,4-Oxazines?
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5752
_journal_page_last               5755
_journal_paper_doi               10.1021/acs.orglett.6b03047
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C18 H17 N O3 S'
_chemical_formula_weight         327.39
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 97.160(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1754(3)
_cell_length_b                   12.8893(3)
_cell_length_c                   9.6352(2)
_cell_measurement_reflns_used    2614
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      71.1090
_cell_measurement_theta_min      3.4160
_cell_volume                     1623.51(6)
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 16.3291
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6088
_diffrn_reflns_theta_full        71.86
_diffrn_reflns_theta_max         71.86
_diffrn_reflns_theta_min         4.82
_exptl_absorpt_coefficient_mu    1.893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0453
_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)+(0.0703P)²+0.3861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1408
_reflns_number_gt                2564
_reflns_number_total             3108
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03047_si_002.cif
_cod_data_source_block           compound-2a
_cod_original_cell_volume        1623.52(7)
_cod_database_code               1555926
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.39755(4) 0.84357(4) 0.14022(6) 0.0519(2) Uani 1 1 d .
O3 O 0.14291(11) 0.93340(12) 0.08411(15) 0.0569(4) Uani 1 1 d .
C7 C 0.19622(17) 0.84414(18) 0.0690(2) 0.0510(5) Uani 1 1 d .
N1 N 0.29419(14) 0.85923(15) 0.02191(18) 0.0536(5) Uani 1 1 d .
O2 O 0.38915(13) 0.74391(12) 0.20083(18) 0.0637(4) Uani 1 1 d .
O1 O 0.48273(12) 0.86712(14) 0.06732(18) 0.0664(5) Uani 1 1 d .
C6 C 0.41143(16) 1.04039(17) 0.2426(2) 0.0527(5) Uani 1 1 d .
H6 H 0.4351 1.0590 0.1591 0.063 Uiso 1 1 calc R
C1 C 0.38723(14) 0.93800(16) 0.2682(2) 0.0454(5) Uani 1 1 d .
C5 C 0.39986(17) 1.11387(18) 0.3429(2) 0.0564(6) Uani 1 1 d .
H5 H 0.4152 1.1827 0.3257 0.068 Uiso 1 1 calc R
C4 C 0.36598(16) 1.08814(18) 0.4687(2) 0.0531(5) Uani 1 1 d .
C9 C 0.06485(18) 0.72576(19) 0.1489(2) 0.0580(6) Uani 1 1 d .
C8 C 0.16255(19) 0.75130(19) 0.0982(3) 0.0599(6) Uani 1 1 d .
H8 H 0.2054 0.6957 0.0853 0.072 Uiso 1 1 calc R
C3 C 0.34414(19) 0.98515(19) 0.4921(2) 0.0602(6) Uani 1 1 d .
H3 H 0.3225 0.9662 0.5768 0.072 Uiso 1 1 calc R
C2 C 0.35362(18) 0.91011(18) 0.3932(2) 0.0567(6) Uani 1 1 d .
H2 H 0.3376 0.8414 0.4102 0.068 Uiso 1 1 calc R
C18 C 0.3540(2) 1.1707(2) 0.5756(3) 0.0769(8) Uani 1 1 d .
H18A H 0.4090 1.2197 0.5772 0.115 Uiso 1 1 calc R
H18B H 0.3555 1.1393 0.6662 0.115 Uiso 1 1 calc R
H18C H 0.2900 1.2058 0.5517 0.115 Uiso 1 1 calc R
C10 C 0.0159(2) 0.7906(2) 0.2326(3) 0.0729(7) Uani 1 1 d .
H10 H 0.0452 0.8543 0.2597 0.087 Uiso 1 1 calc R
C15 C 0.29837(19) 0.9402(2) -0.0758(2) 0.0682(7) Uani 1 1 d .
H15 H 0.3581 0.9506 -0.1162 0.082 Uiso 1 1 calc R
C12 C -0.1207(2) 0.6695(3) 0.2384(4) 0.0899(10) Uani 1 1 d .
H12 H -0.1834 0.6517 0.2666 0.108 Uiso 1 1 calc R
C17 C 0.1258(2) 0.9944(3) -0.0413(3) 0.0739(8) Uani 1 1 d .
H17A H 0.1045 1.0637 -0.0184 0.089 Uiso 1 1 calc R
H17B H 0.0714 0.9634 -0.1049 0.089 Uiso 1 1 calc R
C14 C 0.0203(2) 0.6299(2) 0.1153(3) 0.0819(8) Uani 1 1 d .
H14 H 0.0533 0.5830 0.0630 0.098 Uiso 1 1 calc R
C16 C 0.2196(2) 1.0009(3) -0.1104(3) 0.0775(8) Uani 1 1 d .
H16 H 0.2228 1.0497 -0.1808 0.093 Uiso 1 1 calc R
C11 C -0.0762(2) 0.7626(3) 0.2770(4) 0.0863(9) Uani 1 1 d .
H11 H -0.1080 0.8075 0.3335 0.104 Uiso 1 1 calc R
C13 C -0.0726(3) 0.6032(3) 0.1585(4) 0.0960(10) Uani 1 1 d .
H13 H -0.1023 0.5395 0.1327 0.115 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 0.0181 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
O2 S1 O1 120.02(10)
O2 S1 N1 106.87(10)
O1 S1 N1 105.16(10)
O2 S1 C1 108.81(10)
O1 S1 C1 109.47(10)
N1 S1 C1 105.52(9)
C7 O3 C17 113.63(18)
C8 C7 O3 123.4(2)
C8 C7 N1 122.0(2)
O3 C7 N1 114.51(19)
C15 N1 C7 115.02(19)
C15 N1 S1 116.54(16)
C7 N1 S1 117.10(14)
C5 C6 C1 118.9(2)
C5 C6 H6 120.6
C1 C6 H6 120.6
C2 C1 C6 120.5(2)
C2 C1 S1 119.65(17)
C6 C1 S1 119.81(16)
C6 C5 C4 121.8(2)
C6 C5 H5 119.1
C4 C5 H5 119.1
C5 C4 C3 118.0(2)
C5 C4 C18 120.3(2)
C3 C4 C18 121.7(2)
C10 C9 C14 117.5(3)
C10 C9 C8 123.5(2)
C14 C9 C8 119.0(2)
C7 C8 C9 127.3(2)
C7 C8 H8 116.4
C9 C8 H8 116.4
C2 C3 C4 121.6(2)
C2 C3 H3 119.2
C4 C3 H3 119.2
C3 C2 C1 119.2(2)
C3 C2 H2 120.4
C1 C2 H2 120.4
C4 C18 H18A 109.5
C4 C18 H18B 109.5
H18A C18 H18B 109.5
C4 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C9 C10 C11 121.1(3)
C9 C10 H10 119.5
C11 C10 H10 119.5
C16 C15 N1 121.1(2)
C16 C15 H15 119.5
N1 C15 H15 119.5
C13 C12 C11 119.4(3)
C13 C12 H12 120.3
C11 C12 H12 120.3
O3 C17 C16 111.0(2)
O3 C17 H17A 109.4
C16 C17 H17A 109.4
O3 C17 H17B 109.4
C16 C17 H17B 109.4
H17A C17 H17B 108.0
C13 C14 C9 121.0(3)
C13 C14 H14 119.5
C9 C14 H14 119.5
C15 C16 C17 122.2(3)
C15 C16 H16 118.9
C17 C16 H16 118.9
C12 C11 C10 120.6(3)
C12 C11 H11 119.7
C10 C11 H11 119.7
C12 C13 C14 120.5(3)
C12 C13 H13 119.8
C14 C13 H13 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4211(17)
S1 O1 1.4288(16)
S1 N1 1.6756(19)
S1 C1 1.750(2)
O3 C7 1.365(3)
O3 C17 1.435(3)
C7 C8 1.319(3)
C7 N1 1.434(3)
N1 C15 1.411(3)
C6 C5 1.375(3)
C6 C1 1.387(3)
C6 H6 0.9300
C1 C2 1.382(3)
C5 C4 1.383(3)
C5 H5 0.9300
C4 C3 1.383(3)
C4 C18 1.503(3)
C9 C10 1.376(4)
C9 C14 1.389(4)
C9 C8 1.470(3)
C8 H8 0.9300
C3 C2 1.374(3)
C3 H3 0.9300
C2 H2 0.9300
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C10 C11 1.383(4)
C10 H10 0.9300
C15 C16 1.309(4)
C15 H15 0.9300
C12 C13 1.359(5)
C12 C11 1.367(5)
C12 H12 0.9300
C17 C16 1.477(4)
C17 H17A 0.9700
C17 H17B 0.9700
C14 C13 1.384(4)
C14 H14 0.9300
C16 H16 0.9300
C11 H11 0.9300
C13 H13 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132966833
