#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/39/1503962.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_1503962
loop_
_publ_author_name
'Gromov, Alexey'
'Enev, Valentin'
'Mulzer, Johann'
_publ_section_title
;
 A desymmetrization approach toward highly oxygenated cis-decalins.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2884
_journal_page_last               2886
_journal_paper_doi               10.1021/ol900834c
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H16 Cl3 N O5'
_chemical_formula_sum            'C15 H16 Cl3 N O5'
_chemical_formula_weight         396.64
_chemical_name_systematic
; 
(2,2,2-Trichloro-acetyl)-carbamic acid (1R,2S,3S,4S,7R,8S)-
4-methoxymethyl-11-oxatricyclo[6.2.1.0^2,7^]undeca-5,9-
dien-3-yl ester  
;
_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                   9.4608(5)
_cell_length_b                   13.0758(6)
_cell_length_c                   14.0284(8)
_cell_measurement_reflns_used    1230
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.27
_cell_measurement_theta_min      3.89
_cell_volume                     1735.42(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker X8 APEXII CCD'
_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  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            116235
_diffrn_reflns_theta_full        30.11
_diffrn_reflns_theta_max         30.11
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.553
_exptl_absorpt_correction_T_max  0.9729
_exptl_absorpt_correction_T_min  0.8742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         5087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0276
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0492P)²+0.4987P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0779
_reflns_number_gt                4833
_reflns_number_total             5087
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900834c_si_001.cif
_cod_data_source_block           AlGr756
_cod_depositor_comments
;
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      P212121
_cod_database_code               1503962
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
Cl1 Cl 0.11461(4) 1.10902(3) -0.08437(3) 0.01994(8) Uani 1 1 d .
Cl2 Cl -0.14982(4) 1.06602(3) 0.01202(3) 0.02256(8) Uani 1 1 d .
Cl3 Cl 0.00287(5) 1.25106(3) 0.05281(3) 0.02964(10) Uani 1 1 d .
O1 O 0.13813(17) 1.11152(10) 0.17398(9) 0.0305(3) Uani 1 1 d .
O2 O 0.21365(14) 0.92465(9) 0.23831(7) 0.0205(2) Uani 1 1 d .
O3 O 0.22312(12) 0.80988(8) 0.11778(7) 0.0152(2) Uani 1 1 d .
O4 O 0.08357(11) 0.53202(9) 0.06229(8) 0.0183(2) Uani 1 1 d .
O5 O 0.57182(11) 0.65208(8) 0.08543(7) 0.01504(19) Uani 1 1 d .
N1 N 0.12572(13) 0.96218(9) 0.08847(8) 0.0131(2) Uani 1 1 d .
H1 H 0.0993 0.9351 0.0339 0.016 Uiso 1 1 calc R
C1 C 0.01991(16) 1.12075(11) 0.02388(10) 0.0156(3) Uani 1 1 d .
C2 C 0.10213(16) 1.06489(12) 0.10481(10) 0.0156(2) Uani 1 1 d .
C3 C 0.19075(15) 0.90045(11) 0.15694(10) 0.0136(2) Uani 1 1 d .
C4 C 0.28742(16) 0.73541(11) 0.18321(9) 0.0139(2) Uani 1 1 d .
H4 H 0.2433 0.7426 0.2476 0.017 Uiso 1 1 calc R
C5 C 0.44485(15) 0.75725(11) 0.19070(9) 0.0132(2) Uani 1 1 d .
H5 H 0.4590 0.8245 0.2233 0.016 Uiso 1 1 calc R
C6 C 0.52754(15) 0.67282(11) 0.24604(10) 0.0142(3) Uani 1 1 d .
H6 H 0.5645 0.6992 0.3081 0.017 Uiso 1 1 calc R
C7 C 0.44372(17) 0.57570(12) 0.25944(10) 0.0174(3) Uani 1 1 d .
H7 H 0.4762 0.5276 0.3052 0.021 Uiso 1 1 calc R
C8 C 0.32661(16) 0.55364(11) 0.21071(11) 0.0172(3) Uani 1 1 d .
H8 H 0.2856 0.4878 0.2180 0.021 Uiso 1 1 calc R
C9 C 0.25643(16) 0.62920(11) 0.14432(10) 0.0147(3) Uani 1 1 d .
H9 H 0.3016 0.6230 0.0801 0.018 Uiso 1 1 calc R
C10 C 0.09901(16) 0.60832(12) 0.13361(11) 0.0179(3) Uani 1 1 d .
H10A H 0.0590 0.5841 0.1948 0.021 Uiso 1 1 calc R
H10B H 0.0488 0.6715 0.1145 0.021 Uiso 1 1 calc R
C11 C -0.06038(17) 0.50466(13) 0.04968(13) 0.0211(3) Uani 1 1 d .
H11A H -0.0677 0.4520 0.0003 0.032 Uiso 1 1 calc R
H11B H -0.1145 0.5651 0.0303 0.032 Uiso 1 1 calc R
H11C H -0.0983 0.4781 0.1098 0.032 Uiso 1 1 calc R
C12 C 0.52649(15) 0.75775(11) 0.09365(10) 0.0150(3) Uani 1 1 d .
H12 H 0.4721 0.7848 0.0380 0.018 Uiso 1 1 calc R
C13 C 0.66488(17) 0.81213(12) 0.11438(11) 0.0184(3) Uani 1 1 d .
H13 H 0.6918 0.8790 0.0949 0.022 Uiso 1 1 calc R
C14 C 0.74047(16) 0.74616(13) 0.16561(11) 0.0184(3) Uani 1 1 d .
H14 H 0.8320 0.7569 0.1916 0.022 Uiso 1 1 calc R
C15 C 0.65072(16) 0.65025(11) 0.17411(10) 0.0153(2) Uani 1 1 d .
H15 H 0.7045 0.5858 0.1865 0.018 Uiso 1 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'
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
C3 O3 C4 115.06(10)
C11 O4 C10 111.32(12)
C15 O5 C12 95.71(10)
C2 N1 C3 121.27(12)
C2 N1 H1 119.4
C3 N1 H1 119.4
C2 C1 Cl3 109.38(10)
C2 C1 Cl2 109.43(10)
Cl3 C1 Cl2 109.33(8)
C2 C1 Cl1 109.38(10)
Cl3 C1 Cl1 109.16(8)
Cl2 C1 Cl1 110.14(8)
O1 C2 N1 125.79(14)
O1 C2 C1 119.64(14)
N1 C2 C1 114.57(12)
O2 C3 O3 125.41(14)
O2 C3 N1 125.38(13)
O3 C3 N1 109.21(11)
O3 C4 C5 108.91(12)
O3 C4 C9 107.53(11)
C5 C4 C9 112.66(11)
O3 C4 H4 109.2
C5 C4 H4 109.2
C9 C4 H4 109.2
C4 C5 C6 113.13(12)
C4 C5 C12 115.10(11)
C6 C5 C12 100.86(10)
C4 C5 H5 109.1
C6 C5 H5 109.1
C12 C5 H5 109.1
C7 C6 C5 113.21(12)
C7 C6 C15 108.19(12)
C5 C6 C15 100.69(11)
C7 C6 H6 111.4
C5 C6 H6 111.4
C15 C6 H6 111.4
C8 C7 C6 123.70(13)
C8 C7 H7 118.2
C6 C7 H7 118.2
C7 C8 C9 122.65(14)
C7 C8 H8 118.7
C9 C8 H8 118.7
C8 C9 C4 106.93(11)
C8 C9 C10 111.94(13)
C4 C9 C10 112.83(12)
C8 C9 H9 108.3
C4 C9 H9 108.3
C10 C9 H9 108.3
O4 C10 C9 107.23(11)
O4 C10 H10A 110.3
C9 C10 H10A 110.3
O4 C10 H10B 110.3
C9 C10 H10B 110.3
H10A C10 H10B 108.5
O4 C11 H11A 109.5
O4 C11 H11B 109.5
H11A C11 H11B 109.5
O4 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O5 C12 C13 101.91(11)
O5 C12 C5 102.18(10)
C13 C12 C5 105.13(11)
O5 C12 H12 115.3
C13 C12 H12 115.3
C5 C12 H12 115.3
C14 C13 C12 105.26(13)
C14 C13 H13 127.4
C12 C13 H13 127.4
C13 C14 C15 106.08(14)
C13 C14 H14 127.0
C15 C14 H14 127.0
O5 C15 C14 101.93(11)
O5 C15 C6 99.56(11)
C14 C15 C6 108.07(12)
O5 C15 H15 115.1
C14 C15 H15 115.1
C6 C15 H15 115.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7699(15)
Cl2 C1 1.7658(15)
Cl3 C1 1.7590(15)
O1 C2 1.1955(19)
O2 C3 1.2042(17)
O3 C3 1.3410(17)
O3 C4 1.4700(16)
O4 C11 1.4191(19)
O4 C10 1.4205(18)
O5 C15 1.4510(17)
O5 C12 1.4514(17)
N1 C2 1.3806(18)
N1 C3 1.3974(17)
N1 H1 0.8800
C1 C2 1.558(2)
C4 C5 1.520(2)
C4 C9 1.521(2)
C4 H4 1.0000
C5 C6 1.5599(19)
C5 C12 1.565(2)
C5 H5 1.0000
C6 C7 1.509(2)
C6 C15 1.569(2)
C6 H6 1.0000
C7 C8 1.334(2)
C7 H7 0.9500
C8 C9 1.511(2)
C8 H8 0.9500
C9 C10 1.522(2)
C9 H9 1.0000
C10 H10A 0.9900
C10 H10B 0.9900
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 C13 1.518(2)
C12 H12 1.0000
C13 C14 1.331(2)
C13 H13 0.9500
C14 C15 1.519(2)
C14 H14 0.9500
C15 H15 1.0000
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
C3 N1 C2 O1 3.3(2)
C3 N1 C2 C1 -176.21(12)
Cl3 C1 C2 O1 2.31(19)
Cl2 C1 C2 O1 -117.44(15)
Cl1 C1 C2 O1 121.82(15)
Cl3 C1 C2 N1 -178.15(11)
Cl2 C1 C2 N1 62.11(15)
Cl1 C1 C2 N1 -58.63(15)
C4 O3 C3 O2 2.1(2)
C4 O3 C3 N1 -177.67(11)
C2 N1 C3 O2 10.9(2)
C2 N1 C3 O3 -169.35(13)
C3 O3 C4 C5 -82.78(14)
C3 O3 C4 C9 154.86(12)
O3 C4 C5 C6 -171.21(10)
C9 C4 C5 C6 -52.00(15)
O3 C4 C5 C12 -55.99(14)
C9 C4 C5 C12 63.23(15)
C4 C5 C6 C7 14.26(16)
C12 C5 C6 C7 -109.21(12)
C4 C5 C6 C15 129.51(12)
C12 C5 C6 C15 6.04(13)
C5 C6 C7 C8 15.4(2)
C15 C6 C7 C8 -95.34(17)
C6 C7 C8 C9 -6.9(2)
C7 C8 C9 C4 -29.82(19)
C7 C8 C9 C10 -153.86(15)
O3 C4 C9 C8 178.43(11)
C5 C4 C9 C8 58.41(15)
O3 C4 C9 C10 -58.08(15)
C5 C4 C9 C10 -178.09(12)
C11 O4 C10 C9 177.87(13)
C8 C9 C10 O4 -84.13(14)
C4 C9 C10 O4 155.19(12)
C15 O5 C12 C13 50.39(12)
C15 O5 C12 C5 -58.17(12)
C4 C5 C12 O5 -91.02(13)
C6 C5 C12 O5 31.09(13)
C4 C5 C12 C13 162.90(12)
C6 C5 C12 C13 -74.99(13)
O5 C12 C13 C14 -33.51(15)
C5 C12 C13 C14 72.77(14)
C12 C13 C14 C15 1.55(16)
C12 O5 C15 C14 -49.28(12)
C12 O5 C15 C6 61.64(11)
C13 C14 C15 O5 30.84(15)
C13 C14 C15 C6 -73.49(15)
C7 C6 C15 O5 77.58(12)
C5 C6 C15 O5 -41.38(13)
C7 C6 C15 C14 -176.43(12)
C5 C6 C15 C14 64.61(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26591206
2 PubChem 139038321
