#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/52/4025299.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_4025299
loop_
_publ_author_name
'Perla Y. López-Camacho'
'Pedro Joseph-Nathan'
'Bárbara Gordillo-Román'
'Oscar R. Suárez-Castillo'
'Martha S. Morales-Ríos'
_publ_section_title
;
 Cascade [1,3]-Sigmatropic Rearrangements of Ketene O,O-Acetals: Kinetic
 and DFT Level Mechanistic Studies
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1898
_journal_page_last               1910
_journal_paper_doi               10.1021/jo902520z
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C18 H20 N2 O4'
_chemical_formula_sum            'C18 H20 N2 O4'
_chemical_formula_weight         328.36
_chemical_name_systematic
;
Methyl 3-cyano-3a-tert-butyl-2-methoxy-3aH-furo[2,3-b]
indole-8(8aH)-carboxylate.
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 116.728(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.507(1)
_cell_length_b                   7.4079(5)
_cell_length_c                   16.512(1)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     1694.13(19)
_computing_cell_refinement       'Bruker Smart'
_computing_data_collection       'Bruker Smart'
_computing_data_reduction        'Bruker Smart'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_measurement_method       'Phi and omega 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    0.0573
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10903
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         1.50
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.887
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.887
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0430
_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)+(0.0568P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                1943
_reflns_number_total             3334
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902520z_si_002_1.cif
_cod_data_source_block           2e
_cod_original_cell_volume        1694.08(19)
_cod_database_code               4025299
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C2 C 0.75919(13) 0.1607(3) 0.10747(12) 0.0376(4) Uani 1 1 d . . .
C3 C 0.78853(13) 0.0817(2) 0.05126(11) 0.0381(4) Uani 1 1 d . . .
C3A C 0.75864(12) 0.1983(2) -0.03289(11) 0.0369(4) Uani 1 1 d . . .
C3B C 0.66657(13) 0.1268(3) -0.11064(12) 0.0409(5) Uani 1 1 d . . .
C4 C 0.64890(17) -0.0374(3) -0.15556(14) 0.0517(5) Uani 1 1 d . . .
C5 C 0.55650(18) -0.0746(4) -0.22326(14) 0.0611(6) Uani 1 1 d . . .
C6 C 0.48442(19) 0.0512(4) -0.24522(15) 0.0649(7) Uani 1 1 d . . .
C7 C 0.49945(16) 0.2136(4) -0.20031(14) 0.0572(6) Uani 1 1 d . . .
C7A C 0.59089(14) 0.2472(3) -0.13189(12) 0.0438(5) Uani 1 1 d . . .
C8A C 0.72035(13) 0.3686(2) -0.00311(11) 0.0375(4) Uani 1 1 d . . .
H8A H 0.7615 0.4738 0.0041 0.045 Uiso 1 1 calc R . .
C9 C 0.56697(15) 0.5412(3) -0.07264(14) 0.0482(5) Uani 1 1 d . . .
C10 C 0.56467(16) 0.8082(3) 0.00264(16) 0.0631(6) Uani 1 1 d . . .
H10A H 0.6069 0.8831 0.0520 0.095 Uiso 1 1 calc R . .
H10B H 0.5126 0.7660 0.0141 0.095 Uiso 1 1 calc R . .
H10C H 0.5390 0.8769 -0.0526 0.095 Uiso 1 1 calc R . .
C11 C 0.82936(15) -0.0928(3) 0.06582(13) 0.0475(5) Uani 1 1 d . . .
C12 C 0.73448(19) 0.1996(3) 0.23883(15) 0.0660(7) Uani 1 1 d . . .
H12A H 0.7439 0.1329 0.2920 0.099 Uiso 1 1 calc R . .
H12B H 0.6673 0.2283 0.2044 0.099 Uiso 1 1 calc R . .
H12C H 0.7714 0.3092 0.2565 0.099 Uiso 1 1 calc R . .
C13 C 0.84068(14) 0.2477(3) -0.06002(13) 0.0464(5) Uani 1 1 d . . .
C14 C 0.93048(14) 0.3097(3) 0.02365(15) 0.0572(6) Uani 1 1 d . . .
H14A H 0.9526 0.2142 0.0677 0.086 Uiso 1 1 calc R . .
H14B H 0.9150 0.4138 0.0492 0.086 Uiso 1 1 calc R . .
H14C H 0.9803 0.3401 0.0067 0.086 Uiso 1 1 calc R . .
C15 C 0.86794(17) 0.0847(3) -0.10077(16) 0.0650(6) Uani 1 1 d . . .
H15A H 0.8902 -0.0115 -0.0572 0.097 Uiso 1 1 calc R . .
H15B H 0.9183 0.1183 -0.1165 0.097 Uiso 1 1 calc R . .
H15C H 0.8124 0.0450 -0.1541 0.097 Uiso 1 1 calc R . .
C16 C 0.80567(18) 0.3996(3) -0.13038(16) 0.0702(7) Uani 1 1 d . . .
H13C H 0.8557 0.4297 -0.1472 0.105 Uiso 1 1 calc R . .
H16A H 0.7901 0.5039 -0.1050 0.105 Uiso 1 1 calc R . .
H16B H 0.7493 0.3604 -0.1831 0.105 Uiso 1 1 calc R . .
N8 N 0.62375(11) 0.3987(2) -0.07268(10) 0.0437(4) Uani 1 1 d . . .
N11 N 0.86223(16) -0.2346(3) 0.07696(14) 0.0747(6) Uani 1 1 d . . .
O1 O 0.71816(9) 0.32313(17) 0.08254(8) 0.0437(3) Uani 1 1 d . . .
O2 O 0.76578(10) 0.09247(18) 0.18429(8) 0.0519(4) Uani 1 1 d . . .
O9 O 0.48323(11) 0.5580(2) -0.12464(11) 0.0739(5) Uani 1 1 d . . .
O10 O 0.61799(10) 0.65584(19) -0.00585(10) 0.0543(4) Uani 1 1 d . . .
H4A H 0.7025(13) -0.127(3) -0.1385(11) 0.040(5) Uiso 1 1 d . . .
H5A H 0.5443(16) -0.189(3) -0.2543(15) 0.072(7) Uiso 1 1 d . . .
H6A H 0.4213(16) 0.025(3) -0.2927(15) 0.068(7) Uiso 1 1 d . . .
H7A H 0.4530(15) 0.306(3) -0.2135(13) 0.058(6) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C2 O1 117.32(16) . . ?
O2 C2 C3 126.35(17) . . ?
O1 C2 C3 116.32(15) . . ?
C2 C3 C11 123.27(17) . . ?
C2 C3 C3A 109.04(16) . . ?
C11 C3 C3A 127.22(16) . . ?
C3 C3A C3B 110.93(15) . . ?
C3 C3A C8A 99.99(13) . . ?
C3B C3A C8A 101.60(14) . . ?
C3 C3A C13 116.10(15) . . ?
C3B C3A C13 114.42(14) . . ?
C8A C3A C13 111.88(15) . . ?
C4 C3B C7A 119.19(18) . . ?
C4 C3B C3A 129.89(18) . . ?
C7A C3B C3A 110.78(16) . . ?
C3B C4 C5 119.2(2) . . ?
C6 C5 C4 120.0(2) . . ?
C5 C6 C7 122.0(2) . . ?
C6 C7 C7A 117.4(2) . . ?
C7 C7A C3B 122.1(2) . . ?
C7 C7A N8 128.5(2) . . ?
C3B C7A N8 109.42(16) . . ?
N8 C8A O1 109.76(14) . . ?
N8 C8A C3A 106.28(14) . . ?
O1 C8A C3A 107.12(13) . . ?
O9 C9 O10 125.1(2) . . ?
O9 C9 N8 124.5(2) . . ?
O10 C9 N8 110.34(17) . . ?
N11 C11 C3 179.5(2) . . ?
C14 C13 C16 109.50(18) . . ?
C14 C13 C15 108.37(17) . . ?
C16 C13 C15 108.65(17) . . ?
C14 C13 C3A 109.79(15) . . ?
C16 C13 C3A 109.37(16) . . ?
C15 C13 C3A 111.13(16) . . ?
C9 N8 C7A 125.04(17) . . ?
C9 N8 C8A 123.79(16) . . ?
C7A N8 C8A 110.44(15) . . ?
C2 O1 C8A 106.79(13) . . ?
C2 O2 C12 119.07(16) . . ?
C9 O10 C10 115.20(16) . . ?
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
C2 O2 1.326(2) . ?
C2 O1 1.337(2) . ?
C2 C3 1.338(2) . ?
C3 C11 1.412(3) . ?
C3 C3A 1.521(2) . ?
C3A C3B 1.523(3) . ?
C3A C8A 1.564(2) . ?
C3A C13 1.570(2) . ?
C3B C4 1.386(3) . ?
C3B C7A 1.388(3) . ?
C4 C5 1.392(3) . ?
C5 C6 1.372(3) . ?
C6 C7 1.377(3) . ?
C7 C7A 1.381(3) . ?
C7A N8 1.423(2) . ?
C8A N8 1.437(2) . ?
C8A O1 1.469(2) . ?
C9 O9 1.198(2) . ?
C9 O10 1.334(2) . ?
C9 N8 1.375(2) . ?
C10 O10 1.443(2) . ?
C11 N11 1.145(2) . ?
C12 O2 1.439(2) . ?
C13 C14 1.526(3) . ?
C13 C16 1.530(3) . ?
C13 C15 1.532(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139091432
