#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:29:08 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178480 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/01/4030103.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_4030103
loop_
_publ_author_name
'Xu, Hongtao'
'Tang, Huanyu'
'Feng, Huijin'
'Li, Yuanchao'
_publ_section_title
;
 Divergent Total Synthesis of Triptolide, Triptonide, Tripdiolide,
 16-Hydroxytriptolide, and Their Analogues.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10110
_journal_paper_doi               10.1021/jo501744j
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C18 H20 O3'
_chemical_formula_weight         284.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 114.159(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0634(7)
_cell_length_b                   10.2760(6)
_cell_length_c                   12.8460(8)
_cell_measurement_temperature    296(2)
_cell_volume                     1452.96(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7352
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_correction_T_min  0.9828
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2560
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0916P)²+0.0692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1411
_refine_ls_wR_factor_ref         0.1499
_reflns_number_gt                1983
_reflns_number_total             2560
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501744j_si_002.cif
_cod_data_source_block           2013334_0m
_cod_depositor_comments
'Adding full bibliography for 4030102--4030103.cif.'
_cod_database_code               4030103
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
O3 O 1.21567(12) 0.34468(14) 0.99117(14) 0.0692(4) Uani 1 1 d .
O1 O 0.42841(15) -0.06102(19) 0.81847(17) 0.0961(6) Uani 1 1 d .
O2 O 0.48708(12) 0.14380(17) 0.87125(14) 0.0762(5) Uani 1 1 d .
C17 C 1.34150(19) 0.3604(2) 1.0192(2) 0.0740(7) Uani 1 1 d .
H2 H 1.3529 0.3848 0.9521 0.111 Uiso 1 1 calc R
H3 H 1.3829 0.2799 1.0484 0.111 Uiso 1 1 calc R
H1 H 1.3738 0.4270 1.0760 0.111 Uiso 1 1 calc R
C14 C 1.15499(16) 0.24443(17) 0.92035(15) 0.0471(4) Uani 1 1 d .
C8 C 1.03452(15) 0.22713(15) 0.90788(13) 0.0397(4) Uani 1 1 d .
C9 C 0.96679(14) 0.12488(15) 0.84054(12) 0.0371(4) Uani 1 1 d .
C10 C 0.83618(14) 0.10039(15) 0.82665(12) 0.0368(4) Uani 1 1 d .
C5 C 0.82112(14) 0.15728(16) 0.93173(13) 0.0388(4) Uani 1 1 d .
H17 H 0.8829 0.1140 0.9981 0.047 Uiso 1 1 calc R
C4 C 0.69935(16) 0.12513(18) 0.93655(15) 0.0478(5) Uani 1 1 d .
H18 H 0.7176 0.1040 1.0163 0.057 Uiso 1 1 calc R
C3 C 0.63644(16) 0.00955(19) 0.86827(15) 0.0495(5) Uani 1 1 d .
C15 C 0.50847(18) 0.0189(2) 0.84981(17) 0.0621(5) Uani 1 1 d .
C16 C 0.59641(17) 0.2228(2) 0.8992(2) 0.0652(6) Uani 1 1 d .
H19 H 0.6064 0.2835 0.9602 0.078 Uiso 1 1 calc R
H20 H 0.5927 0.2712 0.8331 0.078 Uiso 1 1 calc R
C13 C 1.20606(16) 0.16526(18) 0.86472(15) 0.0506(5) Uani 1 1 d .
H6 H 1.2858 0.1778 0.8737 0.061 Uiso 1 1 calc R
C12 C 1.13609(17) 0.06741(19) 0.79567(16) 0.0529(5) Uani 1 1 d .
H5 H 1.1687 0.0148 0.7563 0.064 Uiso 1 1 calc R
C11 C 1.01909(17) 0.04603(18) 0.78376(14) 0.0468(4) Uani 1 1 d .
H4 H 0.9741 -0.0215 0.7375 0.056 Uiso 1 1 calc R
C7 C 0.98636(16) 0.31996(17) 0.97055(15) 0.0483(4) Uani 1 1 d .
H10 H 0.9979 0.4083 0.9502 0.058 Uiso 1 1 calc R
H9 H 1.0341 0.3100 1.0519 0.058 Uiso 1 1 calc R
C6 C 0.85358(16) 0.30137(17) 0.94644(16) 0.0487(5) Uani 1 1 d .
H8 H 0.8035 0.3481 0.8776 0.058 Uiso 1 1 calc R
H7 H 0.8376 0.3364 1.0091 0.058 Uiso 1 1 calc R
C1 C 0.80917(16) -0.04753(16) 0.82367(15) 0.0459(4) Uani 1 1 d .
H12 H 0.8159 -0.0863 0.7576 0.055 Uiso 1 1 calc R
H11 H 0.8689 -0.0885 0.8914 0.055 Uiso 1 1 calc R
C2 C 0.68462(17) -0.07192(18) 0.81822(16) 0.0534(5) Uani 1 1 d .
H13 H 0.6409 -0.1444 0.7796 0.064 Uiso 1 1 calc R
C18 C 0.75061(16) 0.16243(19) 0.71303(14) 0.0506(5) Uani 1 1 d .
H14 H 0.7612 0.1201 0.6511 0.076 Uiso 1 1 calc R
H15 H 0.7693 0.2533 0.7134 0.076 Uiso 1 1 calc R
H16 H 0.6680 0.1526 0.7038 0.076 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'
O O 0.0106 0.0060 '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
C14 O3 C17 118.62(16)
C15 O2 C16 110.28(15)
O3 C17 H2 109.5
O3 C17 H3 109.5
H2 C17 H3 109.5
O3 C17 H1 109.5
H2 C17 H1 109.5
H3 C17 H1 109.5
O3 C14 C13 123.72(16)
O3 C14 C8 114.63(15)
C13 C14 C8 121.65(16)
C9 C8 C14 118.82(14)
C9 C8 C7 123.49(15)
C14 C8 C7 117.68(15)
C8 C9 C11 118.99(15)
C8 C9 C10 120.66(13)
C11 C9 C10 120.34(15)
C9 C10 C18 107.52(12)
C9 C10 C5 108.56(12)
C18 C10 C5 113.45(13)
C9 C10 C1 111.06(13)
C18 C10 C1 109.26(14)
C5 C10 C1 107.04(12)
C6 C5 C4 114.00(13)
C6 C5 C10 111.05(13)
C4 C5 C10 114.24(13)
C6 C5 H17 105.5
C4 C5 H17 105.5
C10 C5 H17 105.5
C3 C4 C16 100.84(15)
C3 C4 C5 114.51(14)
C16 C4 C5 121.35(16)
C3 C4 H18 106.4
C16 C4 H18 106.4
C5 C4 H18 106.4
C2 C3 C15 127.20(18)
C2 C3 C4 124.84(16)
C15 C3 C4 107.00(16)
O1 C15 O2 121.2(2)
O1 C15 C3 131.0(2)
O2 C15 C3 107.69(17)
O2 C16 C4 104.51(18)
O2 C16 H19 110.9
C4 C16 H19 110.9
O2 C16 H20 110.9
C4 C16 H20 110.9
H19 C16 H20 108.9
C12 C13 C14 118.49(17)
C12 C13 H6 120.8
C14 C13 H6 120.8
C11 C12 C13 121.29(16)
C11 C12 H5 119.4
C13 C12 H5 119.4
C12 C11 C9 120.70(17)
C12 C11 H4 119.7
C9 C11 H4 119.7
C8 C7 C6 114.65(14)
C8 C7 H10 108.6
C6 C7 H10 108.6
C8 C7 H9 108.6
C6 C7 H9 108.6
H10 C7 H9 107.6
C7 C6 C5 110.16(14)
C7 C6 H8 109.6
C5 C6 H8 109.6
C7 C6 H7 109.6
C5 C6 H7 109.6
H8 C6 H7 108.1
C2 C1 C10 111.21(14)
C2 C1 H12 109.4
C10 C1 H12 109.4
C2 C1 H11 109.4
C10 C1 H11 109.4
H12 C1 H11 108.0
C3 C2 C1 120.17(17)
C3 C2 H13 119.9
C1 C2 H13 119.9
C10 C18 H14 109.5
C10 C18 H15 109.5
H14 C18 H15 109.5
C10 C18 H16 109.5
H14 C18 H16 109.5
H15 C18 H16 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C14 1.371(2)
O3 C17 1.419(2)
O1 C15 1.205(3)
O2 C15 1.359(3)
O2 C16 1.463(2)
C17 H2 0.9600
C17 H3 0.9600
C17 H1 0.9600
C14 C13 1.383(2)
C14 C8 1.407(2)
C8 C9 1.393(2)
C8 C7 1.509(2)
C9 C11 1.401(2)
C9 C10 1.532(2)
C10 C18 1.539(2)
C10 C5 1.548(2)
C10 C1 1.552(2)
C5 C6 1.523(2)
C5 C4 1.531(2)
C5 H17 0.9800
C4 C3 1.487(3)
C4 C16 1.514(3)
C4 H18 0.9800
C3 C2 1.326(3)
C3 C15 1.466(3)
C16 H19 0.9700
C16 H20 0.9700
C13 C12 1.377(3)
C13 H6 0.9300
C12 C11 1.374(3)
C12 H5 0.9300
C11 H4 0.9300
C7 C6 1.514(2)
C7 H10 0.9700
C7 H9 0.9700
C6 H8 0.9700
C6 H7 0.9700
C1 C2 1.496(2)
C1 H12 0.9700
C1 H11 0.9700
C2 H13 0.9300
C18 H14 0.9600
C18 H15 0.9600
C18 H16 0.9600
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
C17 O3 C14 C13 -7.0(3)
C17 O3 C14 C8 172.97(16)
O3 C14 C8 C9 -177.89(15)
C13 C14 C8 C9 2.1(2)
O3 C14 C8 C7 1.0(2)
C13 C14 C8 C7 -178.99(16)
C14 C8 C9 C11 -2.6(2)
C7 C8 C9 C11 178.53(15)
C14 C8 C9 C10 178.62(13)
C7 C8 C9 C10 -0.2(2)
C8 C9 C10 C18 98.28(17)
C11 C9 C10 C18 -80.48(18)
C8 C9 C10 C5 -24.83(19)
C11 C9 C10 C5 156.41(14)
C8 C9 C10 C1 -142.24(15)
C11 C9 C10 C1 38.99(19)
C9 C10 C5 C6 56.50(17)
C18 C10 C5 C6 -62.96(18)
C1 C10 C5 C6 176.46(13)
C9 C10 C5 C4 -172.86(13)
C18 C10 C5 C4 67.68(18)
C1 C10 C5 C4 -52.91(18)
C6 C5 C4 C3 150.57(15)
C10 C5 C4 C3 21.4(2)
C6 C5 C4 C16 29.3(2)
C10 C5 C4 C16 -99.91(19)
C16 C4 C3 C2 140.6(2)
C5 C4 C3 C2 8.6(3)
C16 C4 C3 C15 -28.84(19)
C5 C4 C3 C15 -160.86(15)
C16 O2 C15 O1 -175.6(2)
C16 O2 C15 C3 2.6(2)
C2 C3 C15 O1 26.3(4)
C4 C3 C15 O1 -164.6(2)
C2 C3 C15 O2 -151.7(2)
C4 C3 C15 O2 17.5(2)
C15 O2 C16 C4 -21.0(2)
C3 C4 C16 O2 29.66(19)
C5 C4 C16 O2 157.34(15)
O3 C14 C13 C12 179.95(17)
C8 C14 C13 C12 0.0(3)
C14 C13 C12 C11 -1.5(3)
C13 C12 C11 C9 1.0(3)
C8 C9 C11 C12 1.2(2)
C10 C9 C11 C12 179.94(15)
C9 C8 C7 C6 -5.3(2)
C14 C8 C7 C6 175.87(15)
C8 C7 C6 C5 36.2(2)
C4 C5 C6 C7 165.65(13)
C10 C5 C6 C7 -63.59(18)
C9 C10 C1 C2 176.08(13)
C18 C10 C1 C2 -65.48(17)
C5 C10 C1 C2 57.74(18)
C15 C3 C2 C1 164.46(18)
C4 C3 C2 C1 -2.8(3)
C10 C1 C2 C3 -32.1(2)
