#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/68/7216899.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_7216899
loop_
_publ_author_name
'Liu, Chunjian'
'Bao, Guanglin'
'Burnell, D. Jean'
_publ_section_title
;
 Synthetic studies toward the kempane diterpenes.
 Dielsâ€“Alder additions to bicyclic dienes
;
_journal_issue                   20
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2644
_journal_paper_doi               10.1039/b104924k
_journal_year                    2001
_chemical_formula_moiety         'C18 H20 O5 '
_chemical_formula_sum            'C18 H20 O5'
_chemical_formula_weight         316.35
_space_group_IT_number           78
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      78
_symmetry_space_group_name_Hall  'P 4cw'
_symmetry_space_group_name_H-M   'P 43'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.055(3)
_cell_length_b                   9.055(3)
_cell_length_c                   18.635(6)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    299.2
_cell_measurement_theta_max      13.4
_cell_measurement_theta_min      10.1
_cell_volume                     1527.9(9)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction
'teXsan for Windows version 1.06 (MSC, 1997-1999)'
_computing_publication_material
'teXsan for Windows version 1.06 (MSC, 1997-1999)'
_computing_structure_refinement
'teXsan for Windows version 1.06 (MSC, 1997-1999)'
_diffrn_ambient_temperature      299.2
_diffrn_measurement_device       'Rigaku AFC6S'
_diffrn_measurement_method       ω-2θ
_diffrn_orient_matrix_UB_11      0.04590
_diffrn_orient_matrix_UB_12      0.08833
_diffrn_orient_matrix_UB_13      -0.02324
_diffrn_orient_matrix_UB_21      -0.06395
_diffrn_orient_matrix_UB_22      0.06625
_diffrn_orient_matrix_UB_23      0.02963
_diffrn_orient_matrix_UB_31      0.07746
_diffrn_orient_matrix_UB_32      0.00236
_diffrn_orient_matrix_UB_33      0.03823
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.02250
_diffrn_reflns_av_sigmaI/netI    0.064
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1588
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        0.03
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_description       irreg.
_exptl_crystal_F_000             672.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.12
_refine_diff_density_min         -0.11
_refine_ls_extinction_coef       0.0000011(1)
_refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.'
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_all   1.285
_refine_ls_goodness_of_fit_ref   1.360
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     208
_refine_ls_number_reflns         1045
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00008|Fo|²]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0370
_refine_ls_wR_factor_ref         0.0330
_reflns_number_gt                1045
_reflns_number_total             1409
_reflns_threshold_expression     I>1.50σ(I)
_cod_data_source_file            b104924k.txt
_cod_data_source_block           cl-ii-3
_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_cell_volume        1527.8(7)
_cod_original_sg_symbol_H-M      'P 43       '
_cod_original_formula_sum        'C18 H20 O5 '
_cod_database_code               7216899
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'   -x,   -y,1/2+z'
'   -y,   +x,3/4+z'
'   +y,   -x,1/4+z'
loop_
_atom_site_label
_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_calc_flag
O(1) 0.4920(3) 0.2335(3) 0.7043 0.0469(7) 1.000 Uani d
O(2) 0.4787(3) 0.1433(3) 0.8150(2) 0.0573(8) 1.000 Uani d
O(3) 0.2310(3) -0.3004(3) 0.5740(2) 0.082(1) 1.000 Uani d
O(4) 0.6221(3) 0.0423(3) 0.4320(2) 0.0555(8) 1.000 Uani d
O(5) 0.8382(2) 0.0783(3) 0.5824(2) 0.0533(8) 1.000 Uani d
C(1) 0.4368(4) 0.1382(4) 0.7534(2) 0.044(1) 1.000 Uani d
C(2) 0.3262(4) 0.0365(4) 0.7205(2) 0.041(1) 1.000 Uani d
C(3) 0.3636(3) 0.0483(4) 0.6409(2) 0.0367(9) 1.000 Uani d
C(4) 0.4956(3) -0.0458(3) 0.6151(2) 0.0328(9) 1.000 Uani d
C(5) 0.4761(3) -0.1998(4) 0.5758(2) 0.039(1) 1.000 Uani d
C(6) 0.3185(4) -0.2118(4) 0.5491(2) 0.048(1) 1.000 Uani d
C(7) 0.2719(4) -0.1041(4) 0.4936(2) 0.049(1) 1.000 Uani d
C(8) 0.3737(4) -0.0148(4) 0.4658(2) 0.048(1) 1.000 Uani d
C(9) 0.5320(4) -0.0213(4) 0.4862(2) 0.0368(9) 1.000 Uani d
C(10) 0.5789(4) -0.1767(4) 0.5098(2) 0.042(1) 1.000 Uani d
C(11) 0.7406(4) -0.1512(4) 0.5327(2) 0.049(1) 1.000 Uani d
C(12) 0.7366(4) 0.0065(4) 0.5613(2) 0.039(1) 1.000 Uani d
C(13) 0.5758(3) 0.0527(3) 0.5587(2) 0.0338(9) 1.000 Uani d
C(14) 0.5365(4) 0.2130(4) 0.5751(2) 0.046(1) 1.000 Uani d
C(15) 0.4212(4) 0.2064(4) 0.6342(2) 0.042(1) 1.000 Uani d
C(16) 0.3193(4) -0.1144(5) 0.7554(2) 0.059(1) 1.000 Uani d
C(17) 0.5168(5) -0.3334(4) 0.6221(3) 0.064(1) 1.000 Uani d
C(18) 0.1101(4) -0.0992(5) 0.4752(3) 0.080(2) 1.000 Uani d
H(1) 0.2340 0.1010 0.7265 0.049 1.000 Uiso c
H(2) 0.2748 0.0378 0.6123 0.044 1.000 Uiso c
H(3) 0.5617 -0.0575 0.6595 0.037 1.000 Uiso c
H(4) 0.3524 0.0671 0.4219 0.058 1.000 Uiso c
H(5) 0.5658 -0.2573 0.4718 0.046 1.000 Uiso c
H(6) 0.7807 -0.2228 0.5694 0.058 1.000 Uiso c
H(7) 0.8085 -0.1512 0.4891 0.058 1.000 Uiso c
H(8) 0.6254 0.2677 0.5952 0.053 1.000 Uiso c
H(9) 0.4910 0.2518 0.5327 0.053 1.000 Uiso c
H(10) 0.3393 0.2826 0.6252 0.047 1.000 Uiso c
H(11) 0.2783 -0.1105 0.8038 0.068 1.000 Uiso c
H(12) 0.2656 -0.1860 0.7274 0.068 1.000 Uiso c
H(13) 0.4183 -0.1516 0.7609 0.068 1.000 Uiso c
H(14) 0.4379 -0.3453 0.6625 0.075 1.000 Uiso c
H(15) 0.5317 -0.4201 0.5869 0.075 1.000 Uiso c
H(16) 0.6189 -0.3159 0.6426 0.075 1.000 Uiso c
H(17) 0.0667 -0.0564 0.5204 0.092 1.000 Uiso c
H(18) 0.0931 -0.0465 0.4394 0.092 1.000 Uiso c
H(19) 0.0721 -0.2091 0.4661 0.092 1.000 Uiso c
H(20) 0.6269 0.0035 0.3850 0.067 1.000 Uiso c
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 72 0.002 0.002
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
H 0 80 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O 0 20 0.008 0.006
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 1 3
2 0 1
2 0 -1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(1) O(1) C(15) 109.4(3) ?
C(9) O(4) H(20) 122.4 no
O(1) C(1) O(2) 120.0(4) ?
O(1) C(1) C(2) 111.3(3) ?
O(2) C(1) C(2) 128.6(4) ?
C(1) C(2) C(3) 102.0(3) ?
C(1) C(2) C(16) 114.1(3) ?
C(1) C(2) H(1) 98.6 no
C(3) C(2) C(16) 119.3(3) ?
C(3) C(2) H(1) 104.3 no
C(16) C(2) H(1) 115.7 no
C(2) C(3) C(4) 115.9(3) ?
C(2) C(3) C(15) 102.7(3) ?
C(2) C(3) H(2) 110.2 no
C(4) C(3) C(15) 103.2(3) ?
C(4) C(3) H(2) 114.6 no
C(15) C(3) H(2) 109.2 no
C(3) C(4) C(5) 122.9(3) ?
C(3) C(4) C(13) 104.8(3) ?
C(3) C(4) H(3) 104.9 no
C(5) C(4) C(13) 104.1(3) ?
C(5) C(4) H(3) 110.3 no
C(13) C(4) H(3) 109.4 no
C(4) C(5) C(6) 108.7(3) ?
C(4) C(5) C(10) 100.4(3) ?
C(4) C(5) C(17) 114.1(3) ?
C(6) C(5) C(10) 108.2(3) ?
C(6) C(5) C(17) 110.8(4) ?
C(10) C(5) C(17) 114.0(3) ?
O(3) C(6) C(5) 122.2(4) ?
O(3) C(6) C(7) 120.9(4) ?
C(5) C(6) C(7) 116.8(4) ?
C(6) C(7) C(8) 118.3(4) ?
C(6) C(7) C(18) 117.1(4) ?
C(8) C(7) C(18) 124.6(5) ?
C(7) C(8) C(9) 123.0(4) ?
C(7) C(8) H(4) 124.5 no
C(9) C(8) H(4) 112.3 no
O(4) C(9) C(8) 110.9(3) ?
O(4) C(9) C(10) 114.6(3) ?
O(4) C(9) C(13) 107.2(3) ?
C(8) C(9) C(10) 112.1(3) ?
C(8) C(9) C(13) 116.8(3) ?
C(10) C(9) C(13) 94.3(3) ?
C(5) C(10) C(9) 100.6(3) ?
C(5) C(10) C(11) 111.7(3) ?
C(5) C(10) H(5) 112.5 no
C(9) C(10) C(11) 101.8(3) ?
C(9) C(10) H(5) 115.0 no
C(11) C(10) H(5) 114.1 no
C(10) C(11) C(12) 102.4(3) ?
C(10) C(11) H(6) 115.6 no
C(10) C(11) H(7) 110.6 no
C(12) C(11) H(6) 111.9 no
C(12) C(11) H(7) 107.1 no
H(6) C(11) H(7) 108.8 no
O(5) C(12) C(11) 127.4(4) ?
O(5) C(12) C(13) 127.0(4) ?
C(11) C(12) C(13) 105.6(3) ?
C(4) C(13) C(9) 102.7(3) ?
C(4) C(13) C(12) 105.5(3) ?
C(4) C(13) C(14) 107.5(3) ?
C(9) C(13) C(12) 98.9(3) ?
C(9) C(13) C(14) 121.5(3) ?
C(12) C(13) C(14) 118.7(3) ?
C(13) C(14) C(15) 105.6(3) ?
C(13) C(14) H(8) 110.6 no
C(13) C(14) H(9) 106.5 no
C(15) C(14) H(8) 107.2 no
C(15) C(14) H(9) 108.5 no
H(8) C(14) H(9) 117.8 no
O(1) C(15) C(3) 103.4(3) ?
O(1) C(15) C(14) 109.7(3) ?
O(1) C(15) H(10) 110.2 no
C(3) C(15) C(14) 109.3(3) ?
C(3) C(15) H(10) 113.4 no
C(14) C(15) H(10) 110.6 no
C(2) C(16) H(11) 112.3 no
C(2) C(16) H(12) 113.4 no
C(2) C(16) H(13) 108.9 no
H(11) C(16) H(12) 109.4 no
H(11) C(16) H(13) 105.5 no
H(12) C(16) H(13) 107.0 no
C(5) C(17) H(14) 108.8 no
C(5) C(17) H(15) 106.0 no
C(5) C(17) H(16) 108.0 no
H(14) C(17) H(15) 118.0 no
H(14) C(17) H(16) 111.6 no
H(15) C(17) H(16) 103.8 no
C(7) C(18) H(17) 101.5 no
C(7) C(18) H(18) 112.2 no
C(7) C(18) H(19) 108.8 no
H(17) C(18) H(18) 112.2 no
H(17) C(18) H(19) 111.5 no
H(18) C(18) H(19) 110.3 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(1) 1.354(5) ?
O(1) C(15) 1.476(4) ?
O(2) C(1) 1.210(5) ?
O(3) C(6) 1.219(5) ?
O(4) C(9) 1.421(4) ?
O(4) H(20) 0.94 no
O(5) C(12) 1.192(4) ?
C(1) C(2) 1.492(5) ?
C(2) C(3) 1.525(5) ?
C(2) C(16) 1.514(6) ?
C(2) H(1) 1.02 no
C(3) C(4) 1.544(5) ?
C(3) C(15) 1.529(5) ?
C(3) H(2) 0.97 no
C(4) C(5) 1.584(5) ?
C(4) C(13) 1.559(5) ?
C(4) H(3) 1.03 no
C(5) C(6) 1.515(5) ?
C(5) C(10) 1.557(5) ?
C(5) C(17) 1.530(6) ?
C(6) C(7) 1.482(6) ?
C(7) C(8) 1.332(6) ?
C(7) C(18) 1.505(6) ?
C(8) C(9) 1.484(5) ?
C(8) H(4) 1.12 no
C(9) C(10) 1.535(5) ?
C(9) C(13) 1.558(5) ?
C(10) C(11) 1.543(5) ?
C(10) H(5) 1.02 no
C(11) C(12) 1.525(6) ?
C(11) H(6) 1.01 no
C(11) H(7) 1.02 no
C(12) C(13) 1.516(5) ?
C(13) C(14) 1.526(5) ?
C(14) C(15) 1.520(5) ?
C(14) H(8) 1.02 no
C(14) H(9) 0.96 no
C(15) H(10) 1.03 no
C(16) H(11) 0.98 no
C(16) H(12) 0.96 no
C(16) H(13) 0.96 no
C(17) H(14) 1.04 no
C(17) H(15) 1.03 no
C(17) H(16) 1.01 no
C(18) H(17) 1.01 no
C(18) H(18) 0.83 no
C(18) H(19) 1.07 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O(1) C(11) 3.554(5) 4_665 no
O(1) C(10) 3.599(5) 4_665 no
O(2) O(4) 2.901(4) 2_655 no
O(2) C(8) 3.322(5) 2_655 no
O(2) C(9) 3.378(5) 2_655 no
O(2) C(11) 3.563(5) 4_665 no
O(3) C(8) 3.518(5) 4 no
O(4) C(16) 3.398(5) 2_654 no
O(5) C(18) 3.211(6) 4_655 no
O(5) C(2) 3.267(4) 3_654 no
O(5) C(18) 3.554(6) 1_655 no
O(5) C(1) 3.570(5) 3_654 no
C(11) C(18) 3.544(6) 1_655 no
C(12) C(18) 3.556(6) 4_655 no
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
_geom_torsion_publ_flag
O(1) C(1) C(2) C(3) 19.5(4) no
O(1) C(1) C(2) C(16) 149.4(3) no
O(1) C(15) C(3) C(2) 32.1(4) no
O(1) C(15) C(3) C(4) -88.7(3) no
O(1) C(15) C(14) C(13) 99.1(3) no
O(2) C(1) O(1) C(15) -178.9(4) no
O(2) C(1) C(2) C(3) -160.6(4) no
O(2) C(1) C(2) C(16) -30.6(6) no
O(3) C(6) C(5) C(4) -112.3(4) no
O(3) C(6) C(5) C(10) 139.5(4) no
O(3) C(6) C(5) C(17) 13.9(5) no
O(3) C(6) C(7) C(8) -176.8(4) no
O(3) C(6) C(7) C(18) 6.0(6) no
O(4) C(9) C(8) C(7) 158.1(4) no
O(4) C(9) C(10) C(5) 171.3(3) no
O(4) C(9) C(10) C(11) 56.2(4) no
O(4) C(9) C(13) C(4) -168.9(3) no
O(4) C(9) C(13) C(12) -60.6(3) no
O(4) C(9) C(13) C(14) 71.1(4) no
O(5) C(12) C(11) C(10) -176.3(4) no
O(5) C(12) C(13) C(4) -112.0(4) no
O(5) C(12) C(13) C(9) 142.1(4) no
O(5) C(12) C(13) C(14) 8.5(5) no
C(1) O(1) C(15) C(3) -21.3(4) no
C(1) O(1) C(15) C(14) -137.8(3) no
C(1) C(2) C(3) C(4) 80.7(4) no
C(1) C(2) C(3) C(15) -30.9(4) no
C(2) C(1) O(1) C(15) 1.1(4) no
C(2) C(3) C(4) C(5) 99.6(4) no
C(2) C(3) C(4) C(13) -142.3(3) no
C(2) C(3) C(15) C(14) 148.9(3) no
C(3) C(4) C(5) C(6) 17.1(5) no
C(3) C(4) C(5) C(10) 130.5(3) no
C(3) C(4) C(5) C(17) -107.1(4) no
C(3) C(4) C(13) C(9) -105.6(3) no
C(3) C(4) C(13) C(12) 151.3(3) no
C(3) C(4) C(13) C(14) 23.7(4) no
C(3) C(15) C(14) C(13) -13.6(4) no
C(4) C(3) C(2) C(16) -45.9(5) no
C(4) C(3) C(15) C(14) 28.1(4) no
C(4) C(5) C(6) C(7) 64.1(4) no
C(4) C(5) C(10) C(9) -45.6(3) no
C(4) C(5) C(10) C(11) 61.8(4) no
C(4) C(13) C(9) C(8) 66.0(4) no
C(4) C(13) C(9) C(10) -51.5(3) no
C(4) C(13) C(12) C(11) 67.1(3) no
C(4) C(13) C(14) C(15) -6.5(4) no
C(5) C(4) C(3) C(15) -148.9(3) no
C(5) C(4) C(13) C(9) 24.6(3) no
C(5) C(4) C(13) C(12) -78.6(3) no
C(5) C(4) C(13) C(14) 153.8(3) no
C(5) C(6) C(7) C(8) 6.7(5) no
C(5) C(6) C(7) C(18) -170.5(3) no
C(5) C(10) C(9) C(8) -61.2(4) no
C(5) C(10) C(9) C(13) 60.1(3) no
C(5) C(10) C(11) C(12) -74.4(4) no
C(6) C(5) C(4) C(13) -101.2(3) no
C(6) C(5) C(10) C(9) 68.2(4) no
C(6) C(5) C(10) C(11) 175.5(3) no
C(6) C(7) C(8) C(9) 1.8(6) no
C(7) C(6) C(5) C(10) -44.0(4) no
C(7) C(6) C(5) C(17) -169.7(3) no
C(7) C(8) C(9) C(10) 28.5(5) no
C(7) C(8) C(9) C(13) -78.7(5) no
C(8) C(9) C(10) C(11) -176.2(3) no
C(8) C(9) C(13) C(12) 174.3(3) no
C(8) C(9) C(13) C(14) -54.0(5) no
C(9) C(8) C(7) C(18) 178.9(4) no
C(9) C(10) C(5) C(17) -168.0(3) no
C(9) C(10) C(11) C(12) 32.2(4) no
C(9) C(13) C(12) C(11) -38.9(3) no
C(9) C(13) C(14) C(15) 111.2(4) no
C(10) C(5) C(4) C(13) 12.2(3) no
C(10) C(9) C(13) C(12) 56.8(3) no
C(10) C(9) C(13) C(14) -171.5(3) no
C(10) C(11) C(12) C(13) 4.6(4) no
C(11) C(10) C(5) C(17) -60.7(5) no
C(11) C(10) C(9) C(13) -54.9(3) no
C(11) C(12) C(13) C(14) -172.4(3) no
C(12) C(13) C(14) C(15) -126.0(3) no
C(13) C(4) C(3) C(15) -30.9(3) no
C(13) C(4) C(5) C(17) 134.5(3) no
C(15) C(3) C(2) C(16) -157.6(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198825
