#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/53/4025350.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_4025350
loop_
_publ_author_name
'David M. Hodgson'
'Saifullah Salik'
'David J. Fox'
_publ_section_title
;
 Stereocontrolled Syntheses of (-)-Cubebol and (-)-10-Epicubebol Involving
 Intramolecular Cyclopropanation of α-Lithiated Epoxides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2157
_journal_page_last               2168
_journal_paper_doi               10.1021/jo9022974
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H22 N2 O6'
_chemical_formula_sum            'C18 H22 N2 O6'
_chemical_formula_weight         362.38
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_audit_creation_date             09-05-01
_audit_creation_method           CRYSTALS_ver_12.87
_cell_angle_alpha                90
_cell_angle_beta                 94.9963(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6584(1)
_cell_length_b                   10.1501(2)
_cell_length_c                   15.8737(4)
_cell_measurement_reflns_used    2107
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     908.22(3)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.069
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11707
_diffrn_reflns_theta_full        26.827
_diffrn_reflns_theta_max         27.375
_diffrn_reflns_theta_min         5.157
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.710
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9301
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         1537
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.000094
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 8.68 11.6 5.89 1.73 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0829
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0829
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                1291
_reflns_number_total             2145
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.30
_oxford_diffrn_Wilson_scale      3.81
_oxford_refine_ls_r_factor_ref   0.0455
_oxford_refine_ls_scale          0.801
_oxford_reflns_number_all        1537
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 6096
_cod_data_source_file            jo9022974_si_001.cif
_cod_data_source_block           6096
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' 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 
;
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4025350
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
O1 O 0.8231 0.6398 0.1099 0.0403 1.0000 Uani . . . . . . .
C2 C 0.6402 0.6959 0.1221 0.0293 1.0000 Uani . . . . . . .
O3 O 0.5571 0.7129 0.1976 0.0317 1.0000 Uani . . . . . . .
C4 C 0.6830 0.6512 0.2716 0.0324 1.0000 Uani . . . . . . .
C5 C 0.7033 0.7533 0.3430 0.0324 1.0000 Uani . . . . . . .
C6 C 0.8135 0.8857 0.3176 0.0371 1.0000 Uani . . . . . . .
C7 C 1.0781 0.8772 0.3073 0.0492 1.0000 Uani . . . . . . .
C8 C 0.7637 0.9932 0.3809 0.0443 1.0000 Uani . . . . . . .
C9 C 0.8325 0.6873 0.4208 0.0395 1.0000 Uani . . . . . . .
C10 C 0.6925 0.5674 0.4467 0.0435 1.0000 Uani . . . . . . .
C11 C 0.6571 0.4653 0.3759 0.0445 1.0000 Uani . . . . . . .
C12 C 0.5459 0.5317 0.2965 0.0366 1.0000 Uani . . . . . . .
C13 C 0.3465 0.4928 0.2542 0.0468 1.0000 Uani . . . . . . .
C14 C 0.5173 0.3471 0.4050 0.0581 1.0000 Uani . . . . . . .
C15 C 0.4741 0.7521 0.0533 0.0278 1.0000 Uani . . . . . . .
C16 C 0.2870 0.8328 0.0710 0.0272 1.0000 Uani . . . . . . .
C17 C 0.1308 0.8733 0.0045 0.0297 1.0000 Uani . . . . . . .
N18 N -0.0740 0.9548 0.0232 0.0370 1.0000 Uani . . . . . . .
O19 O -0.0838 0.9930 0.0958 0.0599 1.0000 Uani . . . . . . .
O20 O -0.2254 0.9773 -0.0347 0.0416 1.0000 Uani . . . . . . .
C21 C 0.1515 0.8372 -0.0786 0.0324 1.0000 Uani . . . . . . .
C22 C 0.3422 0.7590 -0.0930 0.0329 1.0000 Uani . . . . . . .
C23 C 0.5058 0.7168 -0.0295 0.0297 1.0000 Uani . . . . . . .
N24 N 0.3655 0.7150 -0.1803 0.0435 1.0000 Uani . . . . . . .
O25 O 0.5434 0.6525 -0.1940 0.0565 1.0000 Uani . . . . . . .
O26 O 0.2043 0.7420 -0.2343 0.0549 1.0000 Uani . . . . . . .
H41 H 0.8415 0.6246 0.2580 0.0397 1.0000 Uiso R . . . . . .
H51 H 0.5400 0.7713 0.3572 0.0367 1.0000 Uiso R . . . . . .
H61 H 0.7323 0.9114 0.2622 0.0441 1.0000 Uiso R . . . . . .
H72 H 1.1302 0.9605 0.2856 0.0728 1.0000 Uiso R . . . . . .
H71 H 1.1061 0.8084 0.2666 0.0729 1.0000 Uiso R . . . . . .
H73 H 1.1653 0.8580 0.3617 0.0729 1.0000 Uiso R . . . . . .
H83 H 0.8252 1.0761 0.3620 0.0650 1.0000 Uiso R . . . . . .
H81 H 0.5961 1.0031 0.3841 0.0651 1.0000 Uiso R . . . . . .
H82 H 0.8373 0.9704 0.4365 0.0650 1.0000 Uiso R . . . . . .
H91 H 0.9891 0.6601 0.4069 0.0468 1.0000 Uiso R . . . . . .
H92 H 0.8476 0.7501 0.4670 0.0469 1.0000 Uiso R . . . . . .
H101 H 0.5370 0.5955 0.4626 0.0529 1.0000 Uiso R . . . . . .
H102 H 0.7798 0.5249 0.4956 0.0528 1.0000 Uiso R . . . . . .
H111 H 0.8145 0.4342 0.3624 0.0520 1.0000 Uiso R . . . . . .
H132 H 0.2846 0.5384 0.2065 0.0570 1.0000 Uiso R . . . . . .
H131 H 0.2702 0.4183 0.2716 0.0571 1.0000 Uiso R . . . . . .
H141 H 0.5005 0.2828 0.3600 0.0858 1.0000 Uiso R . . . . . .
H143 H 0.3633 0.3765 0.4195 0.0858 1.0000 Uiso R . . . . . .
H142 H 0.6031 0.3093 0.4542 0.0861 1.0000 Uiso R . . . . . .
H161 H 0.2669 0.8593 0.1268 0.0327 1.0000 Uiso R . . . . . .
H211 H 0.0396 0.8656 -0.1225 0.0377 1.0000 Uiso R . . . . . .
H231 H 0.6365 0.6646 -0.0421 0.0361 1.0000 Uiso R . . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . O3 . 125.234 yes
O1 . C2 . C15 . 123.713 yes
O3 . C2 . C15 . 111.033 yes
C2 . O3 . C4 . 118.763 yes
O3 . C4 . C5 . 107.771 yes
O3 . C4 . C12 . 109.193 yes
C5 . C4 . C12 . 110.890 yes
O3 . C4 . H41 . 109.4 no
C5 . C4 . H41 . 109.8 no
C12 . C4 . H41 . 109.7 no
C4 . C5 . C6 . 113.533 yes
C4 . C5 . C9 . 107.472 yes
C6 . C5 . C9 . 114.499 yes
C4 . C5 . H51 . 106.4 no
C6 . C5 . H51 . 107.7 no
C9 . C5 . H51 . 106.7 no
C5 . C6 . C7 . 113.571 yes
C5 . C6 . C8 . 110.256 yes
C7 . C6 . C8 . 110.527 yes
C5 . C6 . H61 . 107.1 no
C7 . C6 . H61 . 107.7 no
C8 . C6 . H61 . 107.4 no
C6 . C7 . H72 . 108.7 no
C6 . C7 . H71 . 109.3 no
H72 . C7 . H71 . 108.6 no
C6 . C7 . H73 . 110.1 no
H72 . C7 . H73 . 110.1 no
H71 . C7 . H73 . 110.1 no
C6 . C8 . H83 . 109.0 no
C6 . C8 . H81 . 110.5 no
H83 . C8 . H81 . 108.0 no
C6 . C8 . H82 . 109.9 no
H83 . C8 . H82 . 110.6 no
H81 . C8 . H82 . 109.0 no
C5 . C9 . C10 . 110.041 yes
C5 . C9 . H91 . 108.8 no
C10 . C9 . H91 . 109.8 no
C5 . C9 . H92 . 109.1 no
C10 . C9 . H92 . 109.5 no
H91 . C9 . H92 . 109.6 no
C9 . C10 . C11 . 112.352 yes
C9 . C10 . H101 . 109.7 no
C11 . C10 . H101 . 108.8 no
C9 . C10 . H102 . 109.0 no
C11 . C10 . H102 . 107.9 no
H101 . C10 . H102 . 109.0 no
C10 . C11 . C12 . 109.105 yes
C10 . C11 . C14 . 110.352 yes
C12 . C11 . C14 . 114.293 yes
C10 . C11 . H111 . 108.3 no
C12 . C11 . H111 . 106.2 no
C14 . C11 . H111 . 108.4 no
C11 . C12 . C4 . 112.888 yes
C11 . C12 . C13 . 124.246 yes
C4 . C12 . C13 . 122.838 yes
C12 . C13 . H132 . 120.6 no
C12 . C13 . H131 . 119.5 no
H132 . C13 . H131 . 119.9 no
C11 . C14 . H141 . 109.1 no
C11 . C14 . H143 . 109.3 no
H141 . C14 . H143 . 110.7 no
C11 . C14 . H142 . 108.6 no
H141 . C14 . H142 . 109.9 no
H143 . C14 . H142 . 109.2 no
C2 . C15 . C16 . 121.451 yes
C2 . C15 . C23 . 117.977 yes
C16 . C15 . C23 . 120.514 yes
C15 . C16 . C17 . 118.111 yes
C15 . C16 . H161 . 121.1 no
C17 . C16 . H161 . 120.8 no
C16 . C17 . N18 . 118.437 yes
C16 . C17 . C21 . 123.288 yes
N18 . C17 . C21 . 118.229 yes
C17 . N18 . O19 . 117.923 yes
C17 . N18 . O20 . 117.731 yes
O19 . N18 . O20 . 124.326 yes
C17 . C21 . C22 . 116.354 yes
C17 . C21 . H211 . 121.0 no
C22 . C21 . H211 . 122.6 no
C21 . C22 . C23 . 123.098 yes
C21 . C22 . N24 . 117.865 yes
C23 . C22 . N24 . 118.995 yes
C15 . C23 . C22 . 118.587 yes
C15 . C23 . H231 . 120.9 no
C22 . C23 . H231 . 120.5 no
C22 . N24 . O25 . 117.815 yes
C22 . N24 . O26 . 117.870 yes
O25 . N24 . O26 . 124.309 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.212 yes
C2 . O3 . 1.336 yes
C2 . C15 . 1.491 yes
O3 . C4 . 1.461 yes
C4 . C5 . 1.532 yes
C4 . C12 . 1.511 yes
C4 . H41 . 0.979 no
C5 . C6 . 1.550 yes
C5 . C9 . 1.533 yes
C5 . H51 . 0.987 no
C6 . C7 . 1.523 yes
C6 . C8 . 1.526 yes
C6 . H61 . 0.990 no
C7 . H72 . 0.968 no
C7 . H71 . 0.974 no
C7 . H73 . 0.975 no
C8 . H83 . 0.969 no
C8 . H81 . 0.959 no
C8 . H82 . 0.971 no
C9 . C10 . 1.527 yes
C9 . H91 . 0.972 no
C9 . H92 . 0.970 no
C10 . C11 . 1.530 yes
C10 . H101 . 0.979 no
C10 . H102 . 0.983 no
C11 . C12 . 1.516 yes
C11 . C14 . 1.530 yes
C11 . H111 . 0.986 no
C12 . C13 . 1.322 yes
C13 . H132 . 0.930 no
C13 . H131 . 0.925 no
C14 . H141 . 0.966 no
C14 . H143 . 0.968 no
C14 . H142 . 0.963 no
C15 . C16 . 1.386 yes
C15 . C23 . 1.389 yes
C16 . C17 . 1.379 yes
C16 . H161 . 0.942 no
C17 . N18 . 1.475 yes
C17 . C21 . 1.384 yes
N18 . O19 . 1.222 yes
N18 . O20 . 1.222 yes
C21 . C22 . 1.374 yes
C21 . H211 . 0.945 no
C22 . C23 . 1.376 yes
C22 . N24 . 1.473 yes
C23 . H231 . 0.945 no
N24 . O25 . 1.225 yes
N24 . O26 . 1.227 yes
loop_
_oxford_twin_element_scale_factors
0.533
0.467
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139091462
