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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557375.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_1557375
loop_
_publ_author_name
'Fu, Yifan'
'Ding, Xiaoyu'
'Zhang, Xianglei'
'Shao, Xingcheng'
'Zhao, Jihui'
'Xu, Yechun'
'Luo, Xiaomin'
'Zhao, Weimin'
_publ_section_title
;
 Diterpenoids from the Root Bark of Pinus massoniana and Evaluation of
 Their Phosphodiesterase Type 4D Inhibitory Activity
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.9b01269
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'H2 O, C17 H24 O4'
_chemical_formula_sum            'C17 H26 O5'
_chemical_formula_weight         310.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.0550(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8562(2)
_cell_length_b                   7.7464(2)
_cell_length_c                   10.3400(2)
_cell_measurement_reflns_used    8326
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      74.545
_cell_measurement_theta_min      4.277
_cell_volume                     789.33(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10969
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.643
_diffrn_reflns_theta_min         4.276
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1477 before and 0.0568 after correction. The Ratio of minimum to maximum transmission is 0.8449. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1257 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0299
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0445P)²+0.0802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0779
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                2979
_reflns_number_total             3087
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np9b01269_si_001.cif
_cod_data_source_block           220191038_0m
_cod_database_code               1557375
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.866
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C8(H8A,H8B), C14(H14A,H14B), C3(H3A,H3B), C2(H2A,H2B), C1(H1A,
 H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.10889(15) 0.5380(2) 0.05716(14) 0.0273(3) Uani 1 1 d . . . . .
O5 O 0.94435(15) 0.69846(19) 0.86505(14) 0.0279(3) Uani 1 1 d . . . . .
O2 O 0.36561(14) 0.6183(2) 0.25985(14) 0.0316(4) Uani 1 1 d . . . . .
O1 O 0.38159(14) 0.5073(2) 0.06222(13) 0.0303(3) Uani 1 1 d . . . . .
H1 H 0.297734 0.526700 0.060776 0.045 Uiso 1 1 calc GR . . . .
O4 O 0.96492(17) 0.3601(2) 0.83647(15) 0.0347(4) Uani 1 1 d . . . . .
H4 H 0.940115 0.260250 0.857068 0.052 Uiso 1 1 calc GR . . . .
C12 C 0.74284(17) 0.6724(2) 0.57492(17) 0.0195(4) Uani 1 1 d . . . . .
C10 C 0.87718(18) 0.6340(3) 0.77604(18) 0.0218(4) Uani 1 1 d . . . . .
C13 C 0.6536(2) 0.7867(2) 0.49191(19) 0.0245(4) Uani 1 1 d . . . . .
H13A H 0.685525 0.907297 0.501440 0.029 Uiso 1 1 calc R . . . .
H13B H 0.560079 0.781389 0.524894 0.029 Uiso 1 1 calc R . . . .
C4 C 0.75462(17) 0.4493(2) 0.39366(17) 0.0181(4) Uani 1 1 d . . . . .
C8 C 0.8624(2) 0.3909(3) 0.62034(18) 0.0227(4) Uani 1 1 d . . . . .
H8A H 0.851070 0.264393 0.612200 0.027 Uiso 1 1 calc R . . . .
H8B H 0.951287 0.422101 0.583882 0.027 Uiso 1 1 calc R . . . .
C11 C 0.80492(18) 0.7395(3) 0.68073(18) 0.0221(4) Uani 1 1 d . . . . .
H11 H 0.801395 0.860814 0.693689 0.027 Uiso 1 1 calc R . . . .
C14 C 0.64949(19) 0.7414(2) 0.34856(18) 0.0230(4) Uani 1 1 d . . . . .
H14A H 0.735206 0.777428 0.308057 0.028 Uiso 1 1 calc R . . . .
H14B H 0.573675 0.803298 0.304882 0.028 Uiso 1 1 calc R . . . .
C5 C 0.63026(17) 0.5466(2) 0.33291(16) 0.0177(3) Uani 1 1 d . . . . .
H5 H 0.552641 0.517251 0.389839 0.021 Uiso 1 1 calc R . . . .
C15 C 0.89050(18) 0.5147(3) 0.34307(18) 0.0255(4) Uani 1 1 d . . . . .
H15A H 0.887810 0.514600 0.248280 0.038 Uiso 1 1 calc GR . . . .
H15B H 0.963755 0.438900 0.374107 0.038 Uiso 1 1 calc GR . . . .
H15C H 0.906809 0.632364 0.374480 0.038 Uiso 1 1 calc GR . . . .
C17 C 0.43346(18) 0.5496(3) 0.17764(17) 0.0222(4) Uani 1 1 d . . . . .
C7 C 0.74887(18) 0.4820(2) 0.54283(17) 0.0186(4) Uani 1 1 d . . . . .
H7 H 0.661535 0.430862 0.572219 0.022 Uiso 1 1 calc R . . . .
C6 C 0.58198(18) 0.4931(2) 0.19439(17) 0.0210(4) Uani 1 1 d . . . . .
C3 C 0.7421(2) 0.2542(2) 0.36826(19) 0.0237(4) Uani 1 1 d . . . . .
H3A H 0.827442 0.196739 0.396226 0.028 Uiso 1 1 calc R . . . .
H3B H 0.667880 0.206991 0.420963 0.028 Uiso 1 1 calc R . . . .
C16 C 0.6644(2) 0.5733(3) 0.08420(19) 0.0299(4) Uani 1 1 d . . . . .
H16A H 0.666097 0.699097 0.093820 0.045 Uiso 1 1 calc GR . . . .
H16B H 0.622160 0.543006 0.000712 0.045 Uiso 1 1 calc GR . . . .
H16C H 0.757440 0.528570 0.088024 0.045 Uiso 1 1 calc GR . . . .
C9 C 0.8609(2) 0.4410(3) 0.76316(18) 0.0239(4) Uani 1 1 d . . . . .
H9 H 0.771412 0.407100 0.799380 0.029 Uiso 1 1 calc R . . . .
C2 C 0.7136(2) 0.2124(3) 0.22660(19) 0.0278(4) Uani 1 1 d . . . . .
H2A H 0.708724 0.085664 0.214963 0.033 Uiso 1 1 calc R . . . .
H2B H 0.788445 0.256700 0.173344 0.033 Uiso 1 1 calc R . . . .
C1 C 0.5797(2) 0.2944(3) 0.18194(19) 0.0264(4) Uani 1 1 d . . . . .
H1A H 0.505120 0.247716 0.234384 0.032 Uiso 1 1 calc R . . . .
H1B H 0.561218 0.262799 0.090536 0.032 Uiso 1 1 calc R . . . .
H3C H 0.063(3) 0.553(5) -0.012(3) 0.058(9) Uiso 1 1 d . . . . .
H3D H 0.090(3) 0.445(5) 0.084(3) 0.049(9) Uiso 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 0.0181 0.0091 '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'
O O 0.0492 0.0322 '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
H3C O3 H3D 107(3) . . ?
C17 O1 H1 109.5 . . ?
C9 O4 H4 109.5 . . ?
C13 C12 C7 118.23(15) . . ?
C11 C12 C13 119.21(17) . . ?
C11 C12 C7 122.32(17) . . ?
O5 C10 C11 121.89(18) . . ?
O5 C10 C9 121.54(18) . . ?
C11 C10 C9 116.52(16) . . ?
C12 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
C12 C13 C14 115.12(16) . . ?
H13A C13 H13B 107.5 . . ?
C14 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C5 C4 C7 106.01(13) . . ?
C15 C4 C5 112.81(15) . . ?
C15 C4 C7 109.30(14) . . ?
C15 C4 C3 109.53(16) . . ?
C3 C4 C5 110.23(14) . . ?
C3 C4 C7 108.85(15) . . ?
H8A C8 H8B 108.0 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C9 C8 C7 111.61(16) . . ?
C12 C11 C10 122.83(18) . . ?
C12 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
C13 C14 H14A 109.8 . . ?
C13 C14 H14B 109.8 . . ?
C13 C14 C5 109.36(15) . . ?
H14A C14 H14B 108.2 . . ?
C5 C14 H14A 109.8 . . ?
C5 C14 H14B 109.8 . . ?
C4 C5 H5 104.9 . . ?
C14 C5 C4 109.82(14) . . ?
C14 C5 H5 104.9 . . ?
C14 C5 C6 113.27(15) . . ?
C6 C5 C4 117.78(15) . . ?
C6 C5 H5 104.9 . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C17 O1 121.91(17) . . ?
O2 C17 C6 125.63(16) . . ?
O1 C17 C6 112.39(16) . . ?
C12 C7 C4 112.10(14) . . ?
C12 C7 C8 111.38(14) . . ?
C12 C7 H7 106.4 . . ?
C4 C7 H7 106.4 . . ?
C8 C7 C4 113.61(15) . . ?
C8 C7 H7 106.4 . . ?
C17 C6 C5 107.62(15) . . ?
C17 C6 C16 108.45(15) . . ?
C17 C6 C1 105.21(15) . . ?
C16 C6 C5 114.60(15) . . ?
C16 C6 C1 110.27(17) . . ?
C1 C6 C5 110.21(15) . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C2 C3 C4 112.71(16) . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C6 C16 H16A 109.5 . . ?
C6 C16 H16B 109.5 . . ?
C6 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C9 C10 108.52(15) . . ?
O4 C9 C8 112.79(17) . . ?
O4 C9 H9 108.6 . . ?
C10 C9 C8 109.51(16) . . ?
C10 C9 H9 108.6 . . ?
C8 C9 H9 108.6 . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C3 C2 C1 110.21(16) . . ?
H2A C2 H2B 108.1 . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C6 C1 H1A 109.2 . . ?
C6 C1 H1B 109.2 . . ?
C2 C1 C6 112.21(16) . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
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
O3 H3C 0.84(4) . ?
O3 H3D 0.79(4) . ?
O5 C10 1.230(2) . ?
O2 C17 1.214(2) . ?
O1 H1 0.8400 . ?
O1 C17 1.331(2) . ?
O4 H4 0.8400 . ?
O4 C9 1.410(2) . ?
C12 C13 1.505(2) . ?
C12 C11 1.348(3) . ?
C12 C7 1.513(3) . ?
C10 C11 1.456(3) . ?
C10 C9 1.509(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.523(3) . ?
C4 C5 1.561(2) . ?
C4 C15 1.533(3) . ?
C4 C7 1.565(2) . ?
C4 C3 1.539(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.536(2) . ?
C8 C9 1.527(3) . ?
C11 H11 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C5 1.529(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.557(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 C6 1.535(3) . ?
C7 H7 1.0000 . ?
C6 C16 1.542(3) . ?
C6 C1 1.545(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.521(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C9 H9 1.0000 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.529(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306143
