#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/89/7218955.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_7218955
loop_
_publ_author_name
'Shen, Yunheng'
'He, Yi-Ren'
'Shan, Lei'
'Yang, Xi'
'Wen, Bo'
'Ye, Ji'
'Yuan, Xing'
'Li, Hui-Liang'
'Xu, Xi-ke'
'Zhang, Weidong'
_publ_section_title
;
 Lanceolatins A-G, diterpenoids from Cephalotaxus lanceolata and their
 anti-inflammatory and anti-tumor activities
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA10665B
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H26 O6'
_chemical_formula_weight         350.40
_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
_audit_update_record
;
2012-04-09 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.60690(10)
_cell_length_b                   10.21920(10)
_cell_length_c                   17.6653(2)
_cell_measurement_reflns_used    7669
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      65.96
_cell_measurement_theta_min      5.00
_cell_volume                     1734.29(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11353
_diffrn_reflns_theta_full        66.36
_diffrn_reflns_theta_max         66.36
_diffrn_reflns_theta_min         5.00
_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_T_max  0.9153
_exptl_absorpt_correction_T_min  0.8215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0510P)²+0.4960P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0866
_reflns_number_gt                2917
_reflns_number_total             2960
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra10665b2.cif
_cod_data_source_block           cu_dm12163_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7218955
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
O1 O 0.19816(16) 0.56124(13) 0.53349(7) 0.0385(3) Uani 1 1 d .
H1 H 0.2050 0.5738 0.5803 0.058 Uiso 1 1 calc R
O2 O 0.21917(14) 0.72609(11) 0.20494(6) 0.0269(3) Uani 1 1 d .
O3 O 0.45324(13) 0.90278(12) 0.28146(9) 0.0338(3) Uani 1 1 d .
H3A H 0.5368 0.9057 0.2954 0.051 Uiso 1 1 calc R
O4 O 0.22603(14) 1.16931(11) 0.22528(7) 0.0274(3) Uani 1 1 d .
O5 O 0.13298(13) 1.32083(11) 0.29879(7) 0.0291(3) Uani 1 1 d .
C1 C 0.0950(2) 0.64750(17) 0.50277(10) 0.0280(4) Uani 1 1 d .
H1A H 0.0096 0.6413 0.5349 0.034 Uiso 1 1 calc R
C2 C 0.05955(18) 0.59667(17) 0.42379(10) 0.0253(4) Uani 1 1 d .
H2A H -0.0318 0.6336 0.4090 0.030 Uiso 1 1 calc R
H2B H 0.0483 0.5005 0.4270 0.030 Uiso 1 1 calc R
C3 C 0.16335(18) 0.62613(16) 0.36027(9) 0.0217(3) Uani 1 1 d .
H3 H 0.1321 0.5727 0.3160 0.026 Uiso 1 1 calc R
C4 C 0.15447(16) 0.76588(16) 0.33500(9) 0.0197(3) Uani 1 1 d .
C5 C 0.11214(16) 0.87338(16) 0.37272(9) 0.0200(3) Uani 1 1 d .
C6 C 0.07814(18) 0.89185(17) 0.45558(9) 0.0239(4) Uani 1 1 d .
H6 H -0.0249 0.8838 0.4620 0.029 Uiso 1 1 calc R
C7 C 0.14830(19) 0.78888(17) 0.50582(9) 0.0268(4) Uani 1 1 d .
H7A H 0.1409 0.8191 0.5589 0.032 Uiso 1 1 calc R
H7B H 0.2485 0.7875 0.4928 0.032 Uiso 1 1 calc R
C8 C 0.1236(2) 1.02974(17) 0.48457(10) 0.0303(4) Uani 1 1 d .
H8A H 0.0666 1.0512 0.5296 0.036 Uiso 1 1 calc R
H8B H 0.2216 1.0238 0.5015 0.036 Uiso 1 1 calc R
C9 C 0.11213(19) 1.14408(17) 0.42852(10) 0.0277(4) Uani 1 1 d .
H9A H 0.0129 1.1648 0.4193 0.033 Uiso 1 1 calc R
H9B H 0.1573 1.2227 0.4501 0.033 Uiso 1 1 calc R
C10 C 0.18265(17) 1.10737(16) 0.35385(9) 0.0218(3) Uani 1 1 d .
C11 C 0.10031(16) 0.99018(15) 0.32160(9) 0.0206(3) Uani 1 1 d .
H11 H 0.0001 1.0150 0.3164 0.025 Uiso 1 1 calc R
C12 C 0.15594(17) 0.94648(16) 0.24486(9) 0.0219(3) Uani 1 1 d .
H12 H 0.0816 0.9577 0.2058 0.026 Uiso 1 1 calc R
C13 C 0.18507(16) 0.80090(15) 0.25572(9) 0.0200(3) Uani 1 1 d .
C14 C 0.39602(17) 1.03058(16) 0.28258(11) 0.0269(4) Uani 1 1 d .
H14 H 0.4696 1.0945 0.2672 0.032 Uiso 1 1 calc R
C15 C 0.27960(18) 1.03437(15) 0.22515(10) 0.0252(4) Uani 1 1 d .
H15 H 0.3162 1.0116 0.1738 0.030 Uiso 1 1 calc R
C16 C 0.17646(17) 1.20995(16) 0.29320(10) 0.0233(3) Uani 1 1 d .
C17 C 0.33938(17) 1.06996(16) 0.36139(10) 0.0237(3) Uani 1 1 d .
H17 H 0.3450 0.9910 0.3947 0.028 Uiso 1 1 calc R
C18 C 0.4273(2) 1.1770(2) 0.39794(12) 0.0358(4) Uani 1 1 d .
H18A H 0.5237 1.1468 0.4027 0.054 Uiso 1 1 calc R
H18B H 0.3902 1.1973 0.4483 0.054 Uiso 1 1 calc R
H18C H 0.4245 1.2558 0.3664 0.054 Uiso 1 1 calc R
C19 C 0.31397(19) 0.58350(18) 0.37609(10) 0.0270(4) Uani 1 1 d .
H19A H 0.3711 0.5991 0.3310 0.040 Uiso 1 1 calc R
H19B H 0.3157 0.4901 0.3887 0.040 Uiso 1 1 calc R
H19C H 0.3512 0.6341 0.4186 0.040 Uiso 1 1 calc R
O1S O 0.27515(12) 0.46388(11) 0.18756(7) 0.0256(3) Uani 1 1 d .
H1W H 0.2169 0.4164 0.2217 0.038 Uiso 1 1 d R
H2W H 0.2605 0.5479 0.1969 0.038 Uiso 1 1 d R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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
C1 O1 H1 109.5
C14 O3 H3A 109.5
C16 O4 C15 114.27(12)
O1 C1 C2 106.92(14)
O1 C1 C7 109.61(15)
C2 C1 C7 115.27(14)
O1 C1 H1A 108.3
C2 C1 H1A 108.3
C7 C1 H1A 108.3
C1 C2 C3 117.21(14)
C1 C2 H2A 108.0
C3 C2 H2A 108.0
C1 C2 H2B 108.0
C3 C2 H2B 108.0
H2A C2 H2B 107.2
C4 C3 C2 111.63(14)
C4 C3 C19 112.20(14)
C2 C3 C19 115.10(13)
C4 C3 H3 105.7
C2 C3 H3 105.7
C19 C3 H3 105.7
C5 C4 C13 109.38(15)
C5 C4 C3 130.29(15)
C13 C4 C3 120.17(15)
C4 C5 C11 111.94(14)
C4 C5 C6 130.23(16)
C11 C5 C6 117.83(14)
C5 C6 C7 112.33(14)
C5 C6 C8 111.72(14)
C7 C6 C8 107.86(14)
C5 C6 H6 108.3
C7 C6 H6 108.3
C8 C6 H6 108.3
C6 C7 C1 118.67(14)
C6 C7 H7A 107.6
C1 C7 H7A 107.6
C6 C7 H7B 107.6
C1 C7 H7B 107.6
H7A C7 H7B 107.1
C9 C8 C6 117.08(15)
C9 C8 H8A 108.0
C6 C8 H8A 108.0
C9 C8 H8B 108.0
C6 C8 H8B 108.0
H8A C8 H8B 107.3
C10 C9 C8 109.74(14)
C10 C9 H9A 109.7
C8 C9 H9A 109.7
C10 C9 H9B 109.7
C8 C9 H9B 109.7
H9A C9 H9B 108.2
C16 C10 C9 115.28(14)
C16 C10 C11 104.96(13)
C9 C10 C11 106.35(13)
C16 C10 C17 105.70(13)
C9 C10 C17 114.47(14)
C11 C10 C17 109.63(13)
C5 C11 C12 106.00(13)
C5 C11 C10 110.85(13)
C12 C11 C10 112.08(13)
C5 C11 H11 109.3
C12 C11 H11 109.3
C10 C11 H11 109.3
C11 C12 C13 103.78(13)
C11 C12 C15 107.63(13)
C13 C12 C15 117.30(13)
C11 C12 H12 109.3
C13 C12 H12 109.3
C15 C12 H12 109.3
O2 C13 C4 126.72(15)
O2 C13 C12 124.49(14)
C4 C13 C12 108.62(14)
O3 C14 C15 107.54(14)
O3 C14 C17 112.85(15)
C15 C14 C17 109.70(13)
O3 C14 H14 108.9
C15 C14 H14 108.9
C17 C14 H14 108.9
O4 C15 C14 106.37(13)
O4 C15 C12 106.15(13)
C14 C15 C12 114.03(13)
O4 C15 H15 110.0
C14 C15 H15 110.0
C12 C15 H15 110.0
O5 C16 O4 118.66(15)
O5 C16 C10 127.51(16)
O4 C16 C10 113.83(13)
C18 C17 C14 111.87(15)
C18 C17 C10 113.26(15)
C14 C17 C10 109.05(13)
C18 C17 H17 107.5
C14 C17 H17 107.5
C10 C17 H17 107.5
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C3 C19 H19A 109.5
C3 C19 H19B 109.5
H19A C19 H19B 109.5
C3 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
H1W O1S H2W 106.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.433(2)
O1 H1 0.8400
O2 C13 1.223(2)
O3 C14 1.417(2)
O3 H3A 0.8400
O4 C16 1.356(2)
O4 C15 1.4720(19)
O5 C16 1.212(2)
C1 C2 1.527(2)
C1 C7 1.534(3)
C1 H1A 1.0000
C2 C3 1.531(2)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.499(2)
C3 C19 1.537(2)
C3 H3 1.0000
C4 C5 1.348(2)
C4 C13 1.475(2)
C5 C11 1.501(2)
C5 C6 1.512(2)
C6 C7 1.533(3)
C6 C8 1.561(2)
C6 H6 1.0000
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.536(3)
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.530(2)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C16 1.500(2)
C10 C11 1.544(2)
C10 C17 1.559(2)
C11 C12 1.524(2)
C11 H11 1.0000
C12 C13 1.526(2)
C12 C15 1.530(2)
C12 H12 1.0000
C14 C15 1.510(3)
C14 C17 1.548(2)
C14 H14 1.0000
C15 H15 1.0000
C17 C18 1.526(3)
C17 H17 1.0000
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
O1S H1W 0.9560
O1S H2W 0.8857
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
O1 C1 C2 C3 -77.45(18)
C7 C1 C2 C3 44.7(2)
C1 C2 C3 C4 -75.44(19)
C1 C2 C3 C19 54.0(2)
C2 C3 C4 C5 26.1(2)
C19 C3 C4 C5 -104.8(2)
C2 C3 C4 C13 -148.89(14)
C19 C3 C4 C13 80.21(18)
C13 C4 C5 C11 3.93(18)
C3 C4 C5 C11 -171.44(15)
C13 C4 C5 C6 -175.34(16)
C3 C4 C5 C6 9.3(3)
C4 C5 C6 C7 22.7(2)
C11 C5 C6 C7 -156.51(14)
C4 C5 C6 C8 144.09(17)
C11 C5 C6 C8 -35.1(2)
C5 C6 C7 C1 -71.18(19)
C8 C6 C7 C1 165.28(15)
O1 C1 C7 C6 161.69(14)
C2 C1 C7 C6 41.0(2)
C5 C6 C8 C9 34.4(2)
C7 C6 C8 C9 158.35(15)
C6 C8 C9 C10 -50.4(2)
C8 C9 C10 C16 178.81(15)
C8 C9 C10 C11 62.95(18)
C8 C9 C10 C17 -58.26(19)
C4 C5 C11 C12 -5.61(17)
C6 C5 C11 C12 173.76(14)
C4 C5 C11 C10 -127.45(15)
C6 C5 C11 C10 51.92(18)
C16 C10 C11 C5 173.20(13)
C9 C10 C11 C5 -64.19(16)
C17 C10 C11 C5 60.07(17)
C16 C10 C11 C12 54.99(16)
C9 C10 C11 C12 177.61(13)
C17 C10 C11 C12 -58.13(17)
C5 C11 C12 C13 4.73(16)
C10 C11 C12 C13 125.78(13)
C5 C11 C12 C15 -120.26(14)
C10 C11 C12 C15 0.79(17)
C5 C4 C13 O2 -176.14(16)
C3 C4 C13 O2 -0.2(3)
C5 C4 C13 C12 -0.66(18)
C3 C4 C13 C12 175.25(14)
C11 C12 C13 O2 172.92(15)
C15 C12 C13 O2 -68.6(2)
C11 C12 C13 C4 -2.69(16)
C15 C12 C13 C4 115.83(15)
C16 O4 C15 C14 -59.63(17)
C16 O4 C15 C12 62.18(17)
O3 C14 C15 O4 -177.73(12)
C17 C14 C15 O4 59.18(16)
O3 C14 C15 C12 65.62(18)
C17 C14 C15 C12 -57.47(18)
C11 C12 C15 O4 -58.18(16)
C13 C12 C15 O4 -174.62(13)
C11 C12 C15 C14 58.60(17)
C13 C12 C15 C14 -57.84(19)
C15 O4 C16 O5 178.48(15)
C15 O4 C16 C10 -1.69(19)
C9 C10 C16 O5 6.7(3)
C11 C10 C16 O5 123.37(18)
C17 C10 C16 O5 -120.76(18)
C9 C10 C16 O4 -173.09(14)
C11 C10 C16 O4 -56.45(17)
C17 C10 C16 O4 59.42(18)
O3 C14 C17 C18 111.07(16)
C15 C14 C17 C18 -129.03(15)
O3 C14 C17 C10 -122.86(14)
C15 C14 C17 C10 -2.97(18)
C16 C10 C17 C18 71.28(18)
C9 C10 C17 C18 -56.7(2)
C11 C10 C17 C18 -176.08(14)
C16 C10 C17 C14 -53.98(17)
C9 C10 C17 C14 178.05(14)
C11 C10 C17 C14 58.66(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139049692
