#------------------------------------------------------------------------------
#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/29/4122906.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_4122906
loop_
_publ_author_name
'Yeung, Charles S.'
'Ziegler, Robert E.'
'Porco, Jr, John A'
'Jacobsen, Eric N.'
_publ_section_title
;
 Thiourea-catalyzed enantioselective addition of indoles to pyrones:
 alkaloid cores with quaternary carbons.
;
_journal_issue                   39
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13614
_journal_page_last               13617
_journal_paper_doi               10.1021/ja508523g
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H17 N O3'
_chemical_formula_weight         295.33
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   7.24220(10)
_cell_length_b                   9.75750(10)
_cell_length_c                   20.2541(3)
_cell_measurement_reflns_used    9746
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.7
_cell_measurement_theta_min      4.40
_cell_volume                     1431.27(3)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 v2009.3.0 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Bruker D8 goniometer with CCD area detector  
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'I\mS microfocus tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0119
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            34017
_diffrn_reflns_theta_full        66.27
_diffrn_reflns_theta_max         66.27
_diffrn_reflns_theta_min         4.37
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  0.9012
_exptl_absorpt_correction_T_min  0.8631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2501
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0226
_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)+(0.0236P)²+0.3301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0537
_refine_ls_wR_factor_ref         0.0543
_reflns_number_gt                2444
_reflns_number_total             2501
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja508523g_si_002.cif
_cod_data_source_block           CYeung1206
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 
;
_cod_original_sg_symbol_Hall     P2ac2ab
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               4122906
#BEGIN Tags that were not found in dictionaries:
_refine_ls_abs_structure_hooft   0.04(4)
#END Tags that were not found in dictionaries
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'
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
C1 C 0.48765(19) 0.58448(13) 0.50615(6) 0.0233(3) Uani 1 1 d .
H1 H 0.5001 0.5542 0.5505 0.028 Uiso 1 1 calc R
C2 C 0.62697(18) 0.65497(12) 0.47933(6) 0.0225(3) Uani 1 1 d .
H2 H 0.7346 0.6728 0.5048 0.027 Uiso 1 1 calc R
C3 C 0.61633(17) 0.70458(12) 0.41216(6) 0.0201(3) Uani 1 1 d .
C4 C 0.44490(17) 0.66870(12) 0.37842(6) 0.0186(3) Uani 1 1 d .
C5 C 0.31062(17) 0.59654(12) 0.40939(6) 0.0192(3) Uani 1 1 d .
C6 C 0.12537(17) 0.55932(12) 0.38243(6) 0.0199(3) Uani 1 1 d .
H6A H 0.0871 0.6314 0.3509 0.024 Uiso 1 1 calc R
H6B H 0.0355 0.5596 0.4193 0.024 Uiso 1 1 calc R
C7 C 0.11329(17) 0.41778(12) 0.34675(6) 0.0188(3) Uani 1 1 d .
C8 C 0.22629(17) 0.30607(12) 0.37880(6) 0.0193(3) Uani 1 1 d .
C9 C 0.21997(18) 0.24427(12) 0.44046(6) 0.0233(3) Uani 1 1 d .
H9 H 0.1334 0.2732 0.4728 0.028 Uiso 1 1 calc R
C10 C 0.34409(18) 0.13853(13) 0.45364(6) 0.0249(3) Uani 1 1 d .
H10 H 0.3413 0.0950 0.4956 0.030 Uiso 1 1 calc R
C11 C 0.47170(18) 0.09530(13) 0.40687(6) 0.0250(3) Uani 1 1 d .
H11 H 0.5550 0.0233 0.4172 0.030 Uiso 1 1 calc R
C12 C 0.47830(18) 0.15679(13) 0.34495(6) 0.0233(3) Uani 1 1 d .
H12 H 0.5647 0.1278 0.3125 0.028 Uiso 1 1 calc R
C13 C 0.35504(17) 0.26136(12) 0.33227(6) 0.0194(3) Uani 1 1 d .
C14 C 0.20286(16) 0.41873(12) 0.27844(6) 0.0179(2) Uani 1 1 d .
C15 C 0.11801(17) 0.49972(12) 0.22435(6) 0.0214(3) Uani 1 1 d .
H15A H 0.1839 0.4821 0.1824 0.026 Uiso 1 1 calc R
H15B H 0.1268 0.5988 0.2344 0.026 Uiso 1 1 calc R
C16 C -0.08596(17) 0.45736(13) 0.21782(6) 0.0248(3) Uani 1 1 d .
H16A H -0.1476 0.5172 0.1851 0.030 Uiso 1 1 calc R
H16B H -0.0931 0.3618 0.2015 0.030 Uiso 1 1 calc R
C17 C -0.18640(17) 0.46811(13) 0.28380(6) 0.0251(3) Uani 1 1 d .
H17A H -0.3159 0.4379 0.2782 0.030 Uiso 1 1 calc R
H17B H -0.1878 0.5650 0.2983 0.030 Uiso 1 1 calc R
C18 C -0.09315(17) 0.38020(13) 0.33669(6) 0.0227(3) Uani 1 1 d .
H18A H -0.1024 0.2825 0.3239 0.027 Uiso 1 1 calc R
H18B H -0.1596 0.3920 0.3790 0.027 Uiso 1 1 calc R
O1 O 0.33078(12) 0.55410(8) 0.47379(4) 0.02163(19) Uani 1 1 d .
O2 O 0.73746(12) 0.77293(9) 0.38437(4) 0.0242(2) Uani 1 1 d .
O3 O 0.41886(12) 0.70988(9) 0.31552(4) 0.0221(2) Uani 1 1 d .
N1 N 0.33482(14) 0.33178(10) 0.27084(5) 0.0193(2) Uani 1 1 d .
H3 H 0.518(3) 0.7548(18) 0.2986(8) 0.047(5) 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 0.0181 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 O1 123.58(11)
C2 C1 H1 118.2
O1 C1 H1 118.2
C1 C2 C3 120.96(12)
C1 C2 H2 119.5
C3 C2 H2 119.5
O2 C3 C2 124.79(12)
O2 C3 C4 121.28(11)
C2 C3 C4 113.92(11)
O3 C4 C5 119.45(11)
O3 C4 C3 119.31(11)
C5 C4 C3 121.23(11)
C4 C5 O1 121.27(11)
C4 C5 C6 127.02(11)
O1 C5 C6 111.63(11)
C5 C6 C7 115.77(10)
C5 C6 H6A 108.3
C7 C6 H6A 108.3
C5 C6 H6B 108.3
C7 C6 H6B 108.3
H6A C6 H6B 107.4
C8 C7 C14 99.42(9)
C8 C7 C18 114.07(10)
C14 C7 C18 106.93(10)
C8 C7 C6 114.16(10)
C14 C7 C6 112.95(9)
C18 C7 C6 108.88(10)
C9 C8 C13 119.61(11)
C9 C8 C7 133.07(11)
C13 C8 C7 107.30(10)
C8 C9 C10 118.21(12)
C8 C9 H9 120.9
C10 C9 H9 120.9
C11 C10 C9 121.54(12)
C11 C10 H10 119.2
C9 C10 H10 119.2
C10 C11 C12 120.45(12)
C10 C11 H11 119.8
C12 C11 H11 119.8
C13 C12 C11 117.68(12)
C13 C12 H12 121.2
C11 C12 H12 121.2
C12 C13 C8 122.52(11)
C12 C13 N1 125.74(11)
C8 C13 N1 111.67(10)
N1 C14 C15 124.76(11)
N1 C14 C7 114.80(10)
C15 C14 C7 119.73(10)
C14 C15 C16 108.53(10)
C14 C15 H15A 110.0
C16 C15 H15A 110.0
C14 C15 H15B 110.0
C16 C15 H15B 110.0
H15A C15 H15B 108.4
C17 C16 C15 111.34(10)
C17 C16 H16A 109.4
C15 C16 H16A 109.4
C17 C16 H16B 109.4
C15 C16 H16B 109.4
H16A C16 H16B 108.0
C16 C17 C18 111.38(10)
C16 C17 H17A 109.4
C18 C17 H17A 109.4
C16 C17 H17B 109.4
C18 C17 H17B 109.4
H17A C17 H17B 108.0
C17 C18 C7 112.62(10)
C17 C18 H18A 109.1
C7 C18 H18A 109.1
C17 C18 H18B 109.1
C7 C18 H18B 109.1
H18A C18 H18B 107.8
C1 O1 C5 119.03(10)
C4 O3 H3 112.9(11)
C14 N1 C13 106.79(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3365(19)
C1 O1 1.3447(16)
C1 H1 0.9500
C2 C3 1.4461(17)
C2 H2 0.9500
C3 O2 1.2375(15)
C3 C4 1.4598(17)
C4 O3 1.3491(15)
C4 C5 1.3546(18)
C5 O1 1.3763(14)
C5 C6 1.4933(17)
C6 C7 1.5611(16)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.5098(17)
C7 C14 1.5281(16)
C7 C18 1.5528(17)
C8 C9 1.3875(17)
C8 C13 1.3958(17)
C9 C10 1.3942(18)
C9 H9 0.9500
C10 C11 1.3889(19)
C10 H10 0.9500
C11 C12 1.3911(18)
C11 H11 0.9500
C12 C13 1.3798(18)
C12 H12 0.9500
C13 N1 1.4288(15)
C14 N1 1.2872(15)
C14 C15 1.4841(17)
C15 C16 1.5396(17)
C15 H15A 0.9900
C15 H15B 0.9900
C16 C17 1.5251(18)
C16 H16A 0.9900
C16 H16B 0.9900
C17 C18 1.5295(18)
C17 H17A 0.9900
C17 H17B 0.9900
C18 H18A 0.9900
C18 H18B 0.9900
O3 H3 0.911(19)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 N1 0.911(19) 1.916(19) 2.7670(13) 154.8(16) 3_655
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C1 C2 C3 0.30(19)
C1 C2 C3 O2 178.35(12)
C1 C2 C3 C4 -0.77(16)
O2 C3 C4 O3 0.60(17)
C2 C3 C4 O3 179.76(10)
O2 C3 C4 C5 -178.48(11)
C2 C3 C4 C5 0.67(16)
O3 C4 C5 O1 -179.19(10)
C3 C4 C5 O1 -0.11(17)
O3 C4 C5 C6 -2.62(18)
C3 C4 C5 C6 176.46(11)
C4 C5 C6 C7 91.91(15)
O1 C5 C6 C7 -91.24(12)
C5 C6 C7 C8 38.10(14)
C5 C6 C7 C14 -74.52(13)
C5 C6 C7 C18 166.85(11)
C14 C7 C8 C9 -177.20(13)
C18 C7 C8 C9 -63.77(17)
C6 C7 C8 C9 62.30(17)
C14 C7 C8 C13 0.93(12)
C18 C7 C8 C13 114.35(11)
C6 C7 C8 C13 -119.57(11)
C13 C8 C9 C10 -0.03(17)
C7 C8 C9 C10 177.91(12)
C8 C9 C10 C11 0.15(18)
C9 C10 C11 C12 -0.28(19)
C10 C11 C12 C13 0.26(18)
C11 C12 C13 C8 -0.15(18)
C11 C12 C13 N1 -176.68(11)
C9 C8 C13 C12 0.03(18)
C7 C8 C13 C12 -178.40(11)
C9 C8 C13 N1 177.00(11)
C7 C8 C13 N1 -1.42(13)
C8 C7 C14 N1 -0.16(13)
C18 C7 C14 N1 -119.02(11)
C6 C7 C14 N1 121.22(11)
C8 C7 C14 C15 170.61(10)
C18 C7 C14 C15 51.75(14)
C6 C7 C14 C15 -68.00(14)
N1 C14 C15 C16 116.20(13)
C7 C14 C15 C16 -53.59(14)
C14 C15 C16 C17 53.25(13)
C15 C16 C17 C18 -57.51(14)
C16 C17 C18 C7 57.00(14)
C8 C7 C18 C17 -159.33(10)
C14 C7 C18 C17 -50.46(13)
C6 C7 C18 C17 71.88(12)
C2 C1 O1 C5 0.33(17)
C4 C5 O1 C1 -0.42(16)
C6 C5 O1 C1 -177.47(10)
C15 C14 N1 C13 -170.90(11)
C7 C14 N1 C13 -0.66(13)
C12 C13 N1 C14 178.18(12)
C8 C13 N1 C14 1.32(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101878260
