#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/52/4025226.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_4025226
loop_
_publ_author_name
'Juan A. Faraldos'
'Benson Kariuki'
'Rudolf K. Allemann'
_publ_contact_author
;
B. Kariuki,
School of Chemistry,
Cardiff University,
Main Building
Park Place
Cardiff
CF10 3AT
;
_publ_contact_author_email       kariukib@cardiff.ac.uk
_publ_section_title
;
 Intermediacy of Eudesmane Cation during Catalysis by Aristolochene
 Synthase
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1119
_journal_page_last               1125
_journal_paper_doi               10.1021/jo902397v
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H26 N, Cl'
_chemical_formula_sum            'C14 H26 Cl N'
_chemical_formula_weight         243.81
_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                   6.75500(10)
_cell_length_b                   8.4270(2)
_cell_length_c                   25.7000(4)
_cell_measurement_reflns_used    2944
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.17
_cell_volume                     1462.96(5)
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_collection       'cOLLECT,Nonius BV, 1997-2001'
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SHELXs-97
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD 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  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            3304
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.9650
_exptl_absorpt_correction_T_min  0.9537
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Denzo/Scalepack
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         3304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0416
_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)+(0.0432P)²+0.3923P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1029
_reflns_number_gt                2944
_reflns_number_total             3304
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902397v_si_001.cif
_cod_data_source_block           rka0901
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025226
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-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
C1 C 0.7621(3) 0.0751(2) 0.20338(7) 0.0292(4) Uani 1 1 d . . .
H1A H 0.6984 0.0298 0.2347 0.035 Uiso 1 1 calc R . .
H1B H 0.9068 0.0768 0.2095 0.035 Uiso 1 1 calc R . .
C2 C 0.7179(4) -0.0304(2) 0.15713(7) 0.0377(5) Uani 1 1 d . . .
H2A H 0.5732 -0.0470 0.1544 0.045 Uiso 1 1 calc R . .
H2B H 0.7812 -0.1352 0.1623 0.045 Uiso 1 1 calc R . .
C3 C 0.7946(4) 0.0439(2) 0.10679(8) 0.0434(6) Uani 1 1 d . . .
H3A H 0.7570 -0.0239 0.0769 0.052 Uiso 1 1 calc R . .
H3B H 0.9409 0.0497 0.1080 0.052 Uiso 1 1 calc R . .
C4 C 0.7095(3) 0.2117(2) 0.09885(7) 0.0333(4) Uani 1 1 d . . .
C5 C 0.7695(3) 0.31454(19) 0.14610(6) 0.0240(3) Uani 1 1 d . . .
H5 H 0.9173 0.3131 0.1484 0.029 Uiso 1 1 calc R . .
C6 C 0.8065(4) 0.2882(2) 0.05100(7) 0.0429(5) Uani 1 1 d . . .
H6A H 0.9521 0.2848 0.0552 0.051 Uiso 1 1 calc R . .
H6B H 0.7723 0.2252 0.0198 0.051 Uiso 1 1 calc R . .
C7 C 0.7424(4) 0.4597(2) 0.04246(7) 0.0427(5) Uani 1 1 d . . .
H7A H 0.5982 0.4630 0.0357 0.051 Uiso 1 1 calc R . .
H7B H 0.8110 0.5029 0.0115 0.051 Uiso 1 1 calc R . .
C8 C 0.7904(3) 0.5634(2) 0.09006(7) 0.0339(5) Uani 1 1 d . . .
H8 H 0.7165 0.6651 0.0849 0.041 Uiso 1 1 calc R . .
C9 C 0.7052(3) 0.4879(2) 0.13974(7) 0.0289(4) Uani 1 1 d . . .
H9A H 0.7500 0.5495 0.1704 0.035 Uiso 1 1 calc R . .
H9B H 0.5589 0.4931 0.1385 0.035 Uiso 1 1 calc R . .
C10 C 0.7416(3) 0.3358(2) 0.24317(6) 0.0283(4) Uani 1 1 d . . .
H10A H 0.6909 0.2812 0.2741 0.043 Uiso 1 1 calc R . .
H10B H 0.6821 0.4416 0.2408 0.043 Uiso 1 1 calc R . .
H10C H 0.8858 0.3458 0.2457 0.043 Uiso 1 1 calc R . .
C11 C 0.4844(4) 0.2019(3) 0.09101(8) 0.0461(5) Uani 1 1 d . . .
H11A H 0.4313 0.3085 0.0850 0.069 Uiso 1 1 calc R . .
H11B H 0.4230 0.1561 0.1221 0.069 Uiso 1 1 calc R . .
H11C H 0.4554 0.1346 0.0608 0.069 Uiso 1 1 calc R . .
C12 C 1.0075(3) 0.6084(2) 0.09386(8) 0.0374(5) Uani 1 1 d . . .
C13 C 1.0972(5) 0.6775(4) 0.04527(10) 0.0693(8) Uani 1 1 d . . .
H13A H 1.2192 0.7344 0.0542 0.104 Uiso 1 1 calc R . .
H13B H 1.0032 0.7512 0.0292 0.104 Uiso 1 1 calc R . .
H13C H 1.1279 0.5918 0.0208 0.104 Uiso 1 1 calc R . .
C14 C 1.1141(4) 0.6018(3) 0.13725(10) 0.0498(6) Uani 1 1 d . . .
H14A H 1.2462 0.6405 0.1375 0.060 Uiso 1 1 calc R . .
H14B H 1.0582 0.5583 0.1680 0.060 Uiso 1 1 calc R . .
N1 N 0.6899(2) 0.24256(18) 0.19576(5) 0.0236(3) Uani 1 1 d . . .
H1 H 0.5526 0.2395 0.1932 0.028 Uiso 1 1 calc R . .
Cl1 Cl 1.25346(6) 0.23633(5) 0.218859(18) 0.03526(13) Uani 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'
Cl Cl 0.1484 0.1585 '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
N1 C1 C2 112.61(14) . . ?
N1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
N1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C1 C2 C3 110.92(16) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 C4 111.22(17) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C6 C4 C11 109.89(17) . . ?
C6 C4 C3 109.38(16) . . ?
C11 C4 C3 109.71(18) . . ?
C6 C4 C5 106.38(15) . . ?
C11 C4 C5 113.15(16) . . ?
C3 C4 C5 108.22(15) . . ?
N1 C5 C9 111.82(13) . . ?
N1 C5 C4 110.18(14) . . ?
C9 C5 C4 112.09(14) . . ?
N1 C5 H5 107.5 . . ?
C9 C5 H5 107.5 . . ?
C4 C5 H5 107.5 . . ?
C7 C6 C4 113.07(17) . . ?
C7 C6 H6A 109.0 . . ?
C4 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C4 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C6 C7 C8 111.36(16) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C12 C8 C7 113.39(18) . . ?
C12 C8 C9 114.30(16) . . ?
C7 C8 C9 110.25(16) . . ?
C12 C8 H8 106.1 . . ?
C7 C8 H8 106.1 . . ?
C9 C8 H8 106.1 . . ?
C5 C9 C8 112.14(14) . . ?
C5 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C5 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C12 C13 119.6(2) . . ?
C14 C12 C8 124.53(19) . . ?
C13 C12 C8 115.6(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 120.0 . . ?
C12 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
C10 N1 C1 108.16(13) . . ?
C10 N1 C5 113.27(13) . . ?
C1 N1 C5 111.75(13) . . ?
C10 N1 H1 107.8 . . ?
C1 N1 H1 107.8 . . ?
C5 N1 H1 107.8 . . ?
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
C1 N1 1.506(2) . ?
C1 C2 1.514(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.528(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.540(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C6 1.535(3) . ?
C4 C11 1.536(3) . ?
C4 C5 1.546(2) . ?
C5 N1 1.512(2) . ?
C5 C9 1.533(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.525(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.538(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C12 1.518(3) . ?
C8 C9 1.538(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N1 1.491(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C14 1.329(3) . ?
C12 C13 1.505(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9500 . ?
C14 H14B 0.9500 . ?
N1 H1 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139091413
