#------------------------------------------------------------------------------
#$Date: 2020-02-29 02:19:51 +0200 (Sat, 29 Feb 2020) $
#$Revision: 248550 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/79/4037988.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_4037988
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 O3'
_chemical_formula_weight         333.37
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'I 1 2/a 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                 98.910(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.8870(8)
_cell_length_b                   5.21437(15)
_cell_length_c                   29.1121(8)
_cell_measurement_reflns_used    7532
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.6220
_cell_measurement_theta_min      2.1040
_cell_volume                     3432.35(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            27023
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needles
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0592
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0972P)²+0.5036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1591
_refine_ls_wR_factor_ref         0.1916
_reflns_number_gt                1826
_reflns_number_total             3025
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b03281_si_002.cif
_cod_data_source_block           Compound3aa
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'None' was changed
to 'none' 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_cell_volume        3432.35(19)
_cod_database_code               4037988
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.29787(9) 1.0977(4) 0.07602(6) 0.0555(5) Uani 1 1 d . . .
C16 C 0.38627(10) 0.5565(4) 0.17429(8) 0.0502(6) Uani 1 1 d . . .
O1 O 0.22211(9) 1.4559(4) 0.05389(6) 0.0838(6) Uani 1 1 d . . .
H1 H 0.2479 1.3519 0.0504 0.126 Uiso 1 1 calc R . .
C6 C 0.24347(10) 1.2870(4) 0.13212(8) 0.0509(6) Uani 1 1 d . . .
C5 C 0.28644(10) 1.0941(4) 0.12040(7) 0.0477(6) Uani 1 1 d . . .
C4 C 0.31400(10) 0.9179(4) 0.15213(7) 0.0510(6) Uani 1 1 d . . .
H4 H 0.3049 0.9164 0.1822 0.061 Uiso 1 1 calc R . .
C3 C 0.35479(10) 0.7436(4) 0.14019(8) 0.0494(6) Uani 1 1 d . . .
C12 C 0.34785(12) 0.9358(5) 0.01413(8) 0.0656(7) Uani 1 1 d . . .
H12A H 0.3582 0.7652 0.0048 0.079 Uiso 1 1 calc R . .
H12B H 0.3115 0.9857 -0.0056 0.079 Uiso 1 1 calc R . .
O3 O 0.41013(8) 1.0844(4) -0.03560(5) 0.0739(6) Uani 1 1 d . . .
C2 C 0.36534(11) 0.7508(4) 0.09453(8) 0.0547(6) Uani 1 1 d . . .
H2 H 0.3918 0.6356 0.0847 0.066 Uiso 1 1 calc R . .
C11 C 0.21350(11) 1.4550(5) 0.09924(8) 0.0570(7) Uani 1 1 d . . .
C21 C 0.37899(12) 0.5590(5) 0.22049(9) 0.0681(7) Uani 1 1 d . . .
H21 H 0.3542 0.6811 0.2306 0.082 Uiso 1 1 calc R . .
C1 C 0.33694(11) 0.9266(5) 0.06385(8) 0.0557(6) Uani 1 1 d . . .
C10 C 0.17415(12) 1.6339(5) 0.11174(10) 0.0681(7) Uani 1 1 d . . .
H10 H 0.1544 1.7436 0.0894 0.082 Uiso 1 1 calc R . .
C17 C 0.42369(11) 0.3709(5) 0.16070(9) 0.0613(7) Uani 1 1 d . . .
H17 H 0.4296 0.3629 0.1299 0.074 Uiso 1 1 calc R . .
C18 C 0.45216(12) 0.1982(5) 0.19259(10) 0.0696(8) Uani 1 1 d . . .
H18 H 0.4772 0.0757 0.1829 0.083 Uiso 1 1 calc R . .
C13 C 0.39589(12) 1.1179(5) 0.00640(8) 0.0600(7) Uani 1 1 d . . .
O2 O 0.41921(9) 1.2751(4) 0.03319(7) 0.0894(7) Uani 1 1 d . . .
C7 C 0.23154(12) 1.3112(5) 0.17740(9) 0.0682(8) Uani 1 1 d . . .
H7 H 0.2505 1.2017 0.2002 0.082 Uiso 1 1 calc R . .
C19 C 0.44419(13) 0.2046(5) 0.23815(10) 0.0699(8) Uani 1 1 d . . .
H19 H 0.4635 0.0874 0.2593 0.084 Uiso 1 1 calc R . .
C9 C 0.16413(13) 1.6508(6) 0.15657(10) 0.0783(9) Uani 1 1 d . . .
H9 H 0.1376 1.7717 0.1647 0.094 Uiso 1 1 calc R . .
C20 C 0.40748(13) 0.3852(5) 0.25214(9) 0.0747(8) Uani 1 1 d . . .
H20 H 0.4016 0.3912 0.2830 0.090 Uiso 1 1 calc R . .
C8 C 0.19296(13) 1.4905(6) 0.18957(10) 0.0821(9) Uani 1 1 d . . .
H8 H 0.1864 1.5028 0.2202 0.099 Uiso 1 1 calc R . .
C14 C 0.45386(13) 1.2555(6) -0.05005(9) 0.0829(10) Uani 1 1 d . . .
H14A H 0.4910 1.2415 -0.0291 0.099 Uiso 1 1 calc R . .
H14B H 0.4404 1.4318 -0.0500 0.099 Uiso 1 1 calc R . .
C15 C 0.46171(16) 1.1760(8) -0.09825(10) 0.1104(13) Uani 1 1 d . . .
H15A H 0.4766 1.0038 -0.0976 0.166 Uiso 1 1 calc R . .
H15B H 0.4892 1.2895 -0.1097 0.166 Uiso 1 1 calc R . .
H15C H 0.4243 1.1839 -0.1183 0.166 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 0.0033 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'
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
C1 N1 C5 118.3(2) . . ?
C21 C16 C17 117.2(2) . . ?
C21 C16 C3 121.5(2) . . ?
C17 C16 C3 121.4(2) . . ?
C7 C6 C11 116.4(2) . . ?
C7 C6 C5 120.9(2) . . ?
C11 C6 C5 122.7(2) . . ?
N1 C5 C4 120.6(2) . . ?
N1 C5 C6 116.2(2) . . ?
C4 C5 C6 123.1(2) . . ?
C5 C4 C3 121.5(2) . . ?
C4 C3 C2 116.5(2) . . ?
C4 C3 C16 122.4(2) . . ?
C2 C3 C16 121.1(2) . . ?
C13 C12 C1 113.6(2) . . ?
C13 O3 C14 117.8(2) . . ?
C1 C2 C3 120.4(2) . . ?
O1 C11 C10 116.7(2) . . ?
O1 C11 C6 122.4(2) . . ?
C10 C11 C6 120.9(2) . . ?
C16 C21 C20 121.8(3) . . ?
N1 C1 C2 122.5(2) . . ?
N1 C1 C12 116.5(2) . . ?
C2 C1 C12 121.0(2) . . ?
C9 C10 C11 120.5(2) . . ?
C18 C17 C16 120.7(2) . . ?
C19 C18 C17 121.1(3) . . ?
O2 C13 O3 122.8(3) . . ?
O2 C13 C12 126.9(2) . . ?
O3 C13 C12 110.3(2) . . ?
C8 C7 C6 122.4(2) . . ?
C20 C19 C18 119.1(2) . . ?
C10 C9 C8 120.0(3) . . ?
C19 C20 C21 120.1(3) . . ?
C9 C8 C7 119.8(3) . . ?
O3 C14 C15 106.8(2) . . ?
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
N1 C1 1.349(3) . ?
N1 C5 1.357(3) . ?
C16 C21 1.381(3) . ?
C16 C17 1.390(3) . ?
C16 C3 1.495(3) . ?
O1 C11 1.365(3) . ?
C6 C7 1.393(3) . ?
C6 C11 1.397(3) . ?
C6 C5 1.483(3) . ?
C5 C4 1.384(3) . ?
C4 C3 1.385(3) . ?
C3 C2 1.388(3) . ?
C12 C13 1.496(3) . ?
C12 C1 1.507(3) . ?
O3 C13 1.325(3) . ?
O3 C14 1.451(3) . ?
C2 C1 1.372(3) . ?
C11 C10 1.384(3) . ?
C21 C20 1.382(3) . ?
C10 C9 1.363(4) . ?
C17 C18 1.382(3) . ?
C18 C19 1.367(4) . ?
C13 O2 1.198(3) . ?
C7 C8 1.369(3) . ?
C19 C20 1.365(4) . ?
C9 C8 1.364(4) . ?
C14 C15 1.501(4) . ?
