#------------------------------------------------------------------------------
#$Date: 2025-08-20 15:59:05 +0100 (Wed, 20 Aug 2025) $
#$Revision: 301833 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/64/4116494.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_4116494
loop_
_publ_author_name
'Andrew S. Kende'
'Terrence L. Smalley'
'He Huang'
_publ_section_title
;
 Total Synthesis of (\+-)-Isostemofoline
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7431
_journal_page_last               7432
_journal_paper_doi               10.1021/ja991528a
_journal_volume                  121
_journal_year                    1999
_chemical_formula_sum            'C16 H23 N O3'
_chemical_formula_weight         277.35
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 105.213(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5560(7)
_cell_length_b                   12.2250(7)
_cell_length_c                   11.7344(8)
_cell_measurement_temperature    193(2)
_cell_volume                     1461.22(16)
_computing_cell_refinement       'Siemens SAINT'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL-4.05'
_computing_publication_material  'Siemens SHELXTL-4.05'
_computing_structure_refinement  SHELXTL-4.05(Sheldrick)
_computing_structure_solution    'SHELXS-86 (Sheldrick)'
_diffrn_ambient_temperature      193(2)
_diffrn_measurement_device       'SMART CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5780
_diffrn_reflns_theta_max         23.28
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.800989
_exptl_absorpt_correction_T_min  0.573461
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    NA
_exptl_crystal_description       Plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.152
_refine_ls_goodness_of_fit_obs   1.211
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.152
_refine_ls_restrained_S_obs      1.211
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_obs          0.0603
_refine_ls_shift/esd_max         -0.004
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.3797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1289
_refine_ls_wR_factor_obs         0.1179
_reflns_number_observed          1581
_reflns_number_total             2039
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja991528a.cif
_cod_data_source_block           24
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'NA' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.3797P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.3797P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1461.2(2)
_cod_database_code               4116494
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_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0457(13) 0.066(2) 0.0387(12) 0.0006(11) 0.0186(11) 0.0040(11)
O2 0.0372(12) 0.0410(12) 0.0359(11) -0.0049(9) 0.0116(9) -0.0031(9)
O3 0.0284(11) 0.0452(12) 0.0308(11) -0.0014(9) 0.0050(8) 0.0007(9)
N1 0.0378(15) 0.0395(14) 0.0301(13) -0.0003(11) 0.0064(11) -0.0031(11)
C1 0.030(2) 0.038(2) 0.0295(15) -0.0035(13) 0.0077(13) 0.0008(13)
C2 0.031(2) 0.049(2) 0.033(2) 0.0066(15) 0.0074(14) 0.0025(14)
C3 0.034(2) 0.037(2) 0.041(2) 0.0038(15) 0.0108(14) -0.0033(14)
C4 0.040(2) 0.061(2) 0.049(2) 0.004(2) 0.010(2) -0.013(2)
C5 0.031(2) 0.033(2) 0.032(2) 0.0016(13) 0.0033(13) -0.0011(13)
C6 0.041(2) 0.037(2) 0.037(2) -0.0060(14) 0.0098(14) -0.0059(14)
C7 0.049(2) 0.038(2) 0.047(2) -0.0006(15) 0.017(2) 0.0056(15)
C8 0.031(2) 0.045(2) 0.037(2) 0.0002(14) 0.0100(14) 0.0060(14)
C9 0.031(2) 0.039(2) 0.031(2) -0.0020(13) 0.0041(13) -0.0024(13)
C10 0.033(2) 0.035(2) 0.034(2) -0.0015(13) 0.0063(13) -0.0037(13)
C11 0.040(2) 0.045(2) 0.039(2) 0.0061(15) 0.0082(14) 0.0009(14)
C12 0.040(2) 0.055(2) 0.032(2) 0.0067(15) 0.0019(14) -0.0021(15)
C13 0.036(2) 0.050(2) 0.036(2) 0.0016(15) 0.0101(14) -0.0015(14)
C14 0.046(2) 0.057(2) 0.040(2) -0.003(2) 0.016(2) 0.000(2)
C15 0.046(2) 0.063(2) 0.048(2) 0.005(2) 0.020(2) 0.010(2)
C16 0.065(3) 0.067(2) 0.084(3) 0.000(2) 0.043(2) 0.005(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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.5963(2) 0.4562(2) 0.1380(2) 0.0487(6) Uani 1 d .
O2 O 0.7228(2) 0.50509(15) 0.0206(2) 0.0376(5) Uani 1 d .
O3 O 0.8893(2) 0.39873(15) -0.00610(15) 0.0353(5) Uani 1 d .
N1 N 0.7704(2) 0.3655(2) -0.2869(2) 0.0363(6) Uani 1 d .
C1 C 0.7704(3) 0.4523(2) -0.0675(2) 0.0327(7) Uani 1 d .
C2 C 0.6438(3) 0.4318(2) 0.0592(2) 0.0379(7) Uani 1 d .
C3 C 0.6300(3) 0.3272(2) -0.0113(3) 0.0369(7) Uani 1 d .
H3 H 0.6997(25) 0.2788(21) 0.0353(22) 0.034(7) Uiso 1 d .
C4 C 0.4956(3) 0.2752(3) -0.0299(3) 0.0506(9) Uani 1 d .
H4A H 0.4760(8) 0.2655(14) 0.0466(3) 0.076 Uiso 1 calc R
H4B H 0.4948(6) 0.2039(7) -0.0681(15) 0.076 Uiso 1 calc R
H4C H 0.4291(4) 0.3227(8) -0.0801(14) 0.076 Uiso 1 calc R
C5 C 0.6671(3) 0.3667(2) -0.1210(2) 0.0327(7) Uani 1 d .
H5A H 0.5894(3) 0.4062(2) -0.1713(2) 0.039 Uiso 1 calc R
C6 C 0.7232(3) 0.2944(2) -0.2032(2) 0.0384(7) Uani 1 d .
H6A H 0.6592(3) 0.2378(2) -0.2448(2) 0.046 Uiso 1 calc R
C7 C 0.8538(3) 0.2448(2) -0.1359(3) 0.0436(8) Uani 1 d .
H7A H 0.8457(3) 0.2028(2) -0.0661(3) 0.052 Uiso 1 calc R
H7B H 0.8918(3) 0.1976(2) -0.1871(3) 0.052 Uiso 1 calc R
C8 C 0.9322(3) 0.3493(2) -0.1012(2) 0.0374(7) Uani 1 d .
H8A H 1.0292(3) 0.3371(2) -0.0812(2) 0.045 Uiso 1 calc R
C9 C 0.8825(3) 0.4269(2) -0.2076(2) 0.0343(7) Uani 1 d .
C10 C 0.8105(3) 0.5199(2) -0.1599(2) 0.0344(7) Uani 1 d .
H10A H 0.8697(3) 0.5821(2) -0.1255(2) 0.041 Uiso 1 calc R
C11 C 0.6991(3) 0.5536(2) -0.2650(2) 0.0416(8) Uani 1 d .
H11A H 0.7244(3) 0.6173(2) -0.3063(2) 0.050 Uiso 1 calc R
H11B H 0.6191(3) 0.5721(2) -0.2400(2) 0.050 Uiso 1 calc R
C12 C 0.6766(3) 0.4508(2) -0.3451(2) 0.0441(8) Uani 1 d .
H12A H 0.5855(3) 0.4241(2) -0.3572(2) 0.053 Uiso 1 calc R
H12B H 0.6906(3) 0.4690(2) -0.4231(2) 0.053 Uiso 1 calc R
C13 C 0.9826(3) 0.4655(2) -0.2699(2) 0.0405(8) Uani 1 d .
H13A H 0.9364(3) 0.5084(2) -0.3401(2) 0.049 Uiso 1 calc R
H13B H 1.0443(3) 0.5157(2) -0.2164(2) 0.049 Uiso 1 calc R
C14 C 1.0617(3) 0.3770(3) -0.3095(3) 0.0466(8) Uani 1 d .
H14A H 1.0010(3) 0.3255(3) -0.3621(3) 0.056 Uiso 1 calc R
H14B H 1.1114(3) 0.3355(3) -0.2396(3) 0.056 Uiso 1 calc R
C15 C 1.1567(3) 0.4227(3) -0.3742(3) 0.0508(9) Uani 1 d .
H15A H 1.1057(3) 0.4582(3) -0.4477(3) 0.061 Uiso 1 calc R
H15B H 1.2107(3) 0.4799(3) -0.3244(3) 0.061 Uiso 1 calc R
C16 C 1.2461(3) 0.3402(3) -0.4050(3) 0.0676(11) Uani 1 d .
H16A H 1.3055(16) 0.3766(4) -0.4447(19) 0.101 Uiso 1 calc R
H16B H 1.1941(4) 0.2852(11) -0.4579(16) 0.101 Uiso 1 calc R
H16C H 1.2975(16) 0.3046(13) -0.3329(4) 0.101 Uiso 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
C2 O2 C1 107.7(2)
C1 O3 C8 102.4(2)
C12 N1 C6 114.6(2)
C12 N1 C9 104.9(2)
C6 N1 C9 103.2(2)
O2 C1 O3 105.9(2)
O2 C1 C10 119.6(2)
O3 C1 C10 103.7(2)
O2 C1 C5 105.1(2)
O3 C1 C5 109.4(2)
C10 C1 C5 112.7(2)
O1 C2 O2 120.1(3)
O1 C2 C3 129.4(3)
O2 C2 C3 110.5(2)
C2 C3 C4 112.7(2)
C2 C3 C5 100.8(2)
C4 C3 C5 116.8(2)
C3 C5 C1 100.7(2)
C3 C5 C6 125.2(2)
C1 C5 C6 107.5(2)
N1 C6 C7 99.2(2)
N1 C6 C5 109.2(2)
C7 C6 C5 110.5(2)
C8 C7 C6 99.2(2)
O3 C8 C7 107.5(2)
O3 C8 C9 105.0(2)
C7 C8 C9 104.7(2)
N1 C9 C13 113.2(2)
N1 C9 C8 103.8(2)
C13 C9 C8 116.8(2)
N1 C9 C10 102.1(2)
C13 C9 C10 114.6(2)
C8 C9 C10 104.7(2)
C1 C10 C11 115.3(2)
C1 C10 C9 96.5(2)
C11 C10 C9 104.7(2)
C10 C11 C12 103.6(2)
N1 C12 C11 108.4(2)
C14 C13 C9 115.9(2)
C13 C14 C15 112.4(3)
C16 C15 C14 114.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.199(3)
O2 C2 1.379(3)
O2 C1 1.418(3)
O3 C1 1.431(3)
O3 C8 1.442(3)
N1 C12 1.476(4)
N1 C6 1.491(3)
N1 C9 1.501(3)
C1 C10 1.510(3)
C1 C5 1.523(4)
C2 C3 1.509(4)
C3 C4 1.517(4)
C3 C5 1.519(4)
C5 C6 1.537(4)
C6 C7 1.522(4)
C7 C8 1.518(4)
C8 C9 1.546(4)
C9 C13 1.510(4)
C9 C10 1.551(4)
C10 C11 1.521(4)
C11 C12 1.550(4)
C13 C14 1.512(4)
C14 C15 1.515(4)
C15 C16 1.489(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139120534