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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/86/1508616.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_1508616
loop_
_publ_author_name
'De, Subhadip'
'Ghosh, Santanu'
'Bhunia, Subhajit'
'Sheikh, Javeed Ahmad'
'Bisai, Alakesh'
_publ_section_title
;
 Intramolecular direct dehydrohalide coupling promoted by KO(t)Bu: total
 synthesis of Amaryllidaceae alkaloids anhydrolycorinone and oxoassoanine.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4466
_journal_page_last               4469
_journal_paper_doi               10.1021/ol3019677
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C17 H15 N O3'
_chemical_formula_weight         281.30
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 110.690(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.4692(6)
_cell_length_b                   5.9128(4)
_cell_length_c                   12.8986(7)
_cell_measurement_temperature    296(2)
_cell_volume                     675.61(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6162
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   'Empirical''Bruker SADABS V2.10'
_exptl_absorpt_process_details   'Bruker SADABS V2.10'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.611
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2906
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.611
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1351
_reflns_number_gt                2690
_reflns_number_total             2906
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3019677_si_002.cif
_cod_data_source_block           subahadip_0m
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1508616
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
O3 O 0.19442(13) 0.7485(3) 0.57909(9) 0.0496(3) Uani 1 1 d .
O2 O 0.56778(13) 0.6535(2) 0.94110(10) 0.0488(3) Uani 1 1 d .
C19 C 1.01829(18) 1.0881(4) 1.12381(13) 0.0460(4) Uani 1 1 d .
C18 C 1.14092(18) 1.0587(4) 1.22242(14) 0.0512(4) Uani 1 1 d .
O5 O 0.32099(14) 1.1116(2) 0.54491(9) 0.0510(3) Uani 1 1 d .
C15 C 0.78109(19) 0.6012(4) 1.11160(13) 0.0461(4) Uani 1 1 d .
C13 C 1.03895(19) 0.7078(4) 1.26307(13) 0.0483(4) Uani 1 1 d .
C11 C 0.51409(16) 0.7797(3) 0.84369(12) 0.0348(3) Uani 1 1 d .
C16 C 0.70154(17) 0.7159(3) 1.01767(12) 0.0398(3) Uani 1 1 d .
N3 N 0.77393(14) 0.9104(3) 1.00701(10) 0.0397(3) Uani 1 1 d .
C12 C 0.90684(17) 0.9235(3) 1.09781(12) 0.0380(3) Uani 1 1 d .
C14 C 0.91372(18) 0.7311(3) 1.16427(12) 0.0408(4) Uani 1 1 d .
C20 C 1.14951(18) 0.8714(4) 1.29059(13) 0.0503(4) Uani 1 1 d .
C10 C 0.58140(17) 0.9778(3) 0.82928(12) 0.0354(3) Uani 1 1 d .
C1 C 0.10371(18) 0.5773(4) 0.60221(15) 0.0553(5) Uani 1 1 d .
H1A H 0.1584 0.4372 0.6172 0.083 Uiso 1 1 calc R
H1B H 0.0124 0.5590 0.5394 0.083 Uiso 1 1 calc R
H1C H 0.0793 0.6206 0.6656 0.083 Uiso 1 1 calc R
C2 C 0.32128(15) 0.8126(3) 0.66413(11) 0.0361(3) Uani 1 1 d .
C3 C 0.38477(17) 0.6947(3) 0.76275(13) 0.0363(3) Uani 1 1 d .
C4 C 0.3949(2) 1.2986(4) 0.51777(14) 0.0518(4) Uani 1 1 d .
H4A H 0.4066 1.4169 0.5711 0.078 Uiso 1 1 calc R
H4B H 0.3358 1.3532 0.4453 0.078 Uiso 1 1 calc R
H4C H 0.4925 1.2525 0.5185 0.078 Uiso 1 1 calc R
C5 C 0.39011(16) 1.0128(3) 0.64624(11) 0.0365(3) Uani 1 1 d .
C6 C 0.7175(2) 1.0736(3) 0.91843(13) 0.0464(4) Uani 1 1 d .
C7 C 0.51758(17) 1.0933(3) 0.72838(12) 0.0367(3) Uani 1 1 d .
H5 H 0.346(2) 0.551(5) 0.7788(17) 0.053(6) Uiso 1 1 d .
H6 H 0.564(2) 1.241(5) 0.7189(17) 0.048(5) Uiso 1 1 d .
H12 H 1.046(2) 0.580(6) 1.3107(19) 0.065(7) Uiso 1 1 d .
H13 H 0.759(2) 0.462(6) 1.135(2) 0.062(7) Uiso 1 1 d .
H8 H 0.803(3) 1.105(5) 0.8953(19) 0.065(6) Uiso 1 1 d .
H9 H 1.010(3) 1.211(6) 1.0786(19) 0.065(7) Uiso 1 1 d .
H10 H 1.222(3) 1.172(5) 1.242(2) 0.069(7) Uiso 1 1 d .
H11 H 1.235(2) 0.869(5) 1.3580(19) 0.059(6) Uiso 1 1 d .
H7 H 0.695(3) 1.211(7) 0.951(2) 0.097(10) 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'
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
C2 O3 C1 116.99(13)
C16 O2 C11 117.45(12)
C12 C19 C18 116.73(18)
C12 C19 H9 120.9(16)
C18 C19 H9 122.3(16)
C19 C18 C20 121.04(19)
C19 C18 H10 118.4(16)
C20 C18 H10 120.6(16)
C5 O5 C4 117.23(12)
C16 C15 C14 105.88(16)
C16 C15 H13 127.7(15)
C14 C15 H13 126.2(14)
C20 C13 C14 119.04(18)
C20 C13 H12 120.9(15)
C14 C13 H12 120.0(15)
C10 C11 C3 122.15(13)
C10 C11 O2 122.56(13)
C3 C11 O2 115.26(13)
O2 C16 C15 126.50(17)
O2 C16 N3 121.86(14)
C15 C16 N3 111.63(14)
C16 N3 C12 107.40(13)
C16 N3 C6 125.53(12)
C12 N3 C6 127.04(14)
N3 C12 C19 129.04(15)
N3 C12 C14 107.54(14)
C19 C12 C14 123.41(14)
C13 C14 C12 118.14(17)
C13 C14 C15 134.31(18)
C12 C14 C15 107.54(13)
C13 C20 C18 121.63(15)
C13 C20 H11 123.0(18)
C18 C20 H11 115.4(18)
C11 C10 C7 118.09(13)
C11 C10 C6 122.03(13)
C7 C10 C6 119.87(14)
O3 C1 H1A 109.5
O3 C1 H1B 109.5
H1A C1 H1B 109.5
O3 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O3 C2 C3 124.83(15)
O3 C2 C5 115.39(13)
C3 C2 C5 119.77(13)
C2 C3 C11 119.18(14)
C2 C3 H5 123.9(12)
C11 C3 H5 116.9(12)
O5 C4 H4A 109.5
O5 C4 H4B 109.5
H4A C4 H4B 109.5
O5 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
O5 C5 C7 125.44(15)
O5 C5 C2 114.96(13)
C7 C5 C2 119.60(13)
N3 C6 C10 109.31(14)
N3 C6 H8 104.8(16)
C10 C6 H8 114.8(15)
N3 C6 H7 107.2(19)
C10 C6 H7 112.6(18)
H8 C6 H7 108(3)
C5 C7 C10 121.18(15)
C5 C7 H6 120.6(12)
C10 C7 H6 118.2(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C2 1.3634(17)
O3 C1 1.426(2)
O2 C16 1.3536(18)
O2 C11 1.3938(17)
C19 C12 1.387(2)
C19 C18 1.397(2)
C19 H9 0.92(3)
C18 C20 1.399(3)
C18 H10 0.98(3)
O5 C5 1.3686(17)
O5 C4 1.417(2)
C15 C16 1.360(2)
C15 C14 1.423(3)
C15 H13 0.92(3)
C13 C20 1.377(3)
C13 C14 1.408(2)
C13 H12 0.96(3)
C11 C10 1.377(2)
C11 C3 1.392(2)
C16 N3 1.370(2)
N3 C12 1.3857(17)
N3 C6 1.446(2)
C12 C14 1.412(2)
C20 H11 0.96(2)
C10 C7 1.403(2)
C10 C6 1.5025(19)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.388(2)
C2 C5 1.409(2)
C3 H5 0.98(3)
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
C5 C7 1.3793(19)
C6 H8 0.98(2)
C6 H7 0.97(4)
C7 H6 1.01(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652021
2 PubChem 72193435
