#------------------------------------------------------------------------------
#$Date: 2020-10-19 10:35:42 +0300 (Mon, 19 Oct 2020) $
#$Revision: 258458 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/35/4023578.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_4023578
loop_
_publ_author_name
'Maxime Vitale'
'Guillaume Prestat'
'David Lopes'
'David Madec'
'Claire Kammerer'
'Giovanni Poli'
'Leonard Girnita'
_publ_section_title
;
 New Picropodophyllin Analogs via Palladium-Catalyzed Allylic
 Alkylation-Hiyama Cross-Coupling Sequences
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5795
_journal_page_last               5805
_journal_paper_doi               10.1021/jo800707q
_journal_volume                  73
_journal_year                    2008
_chemical_compound_source
;
?
;
_chemical_formula_moiety         'C22 H20 O8'
_chemical_formula_sum            'C22 H20 O8'
_chemical_formula_weight         412.40
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_date             04-19-07
_audit_creation_method           CRYSTALS_ver_12-03-99
_cell_angle_alpha                90
_cell_angle_beta                 113.226(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.9469(19)
_cell_length_b                   9.2689(8)
_cell_length_c                   22.477(2)
_cell_measurement_reflns_used    100
_cell_measurement_temperature    295
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1
_cell_volume                     3818.8(6)
_computing_cell_refinement
; 
 Denzo/Scalepack (Otwinowski & Minor, 1996) 
;
_computing_data_collection
; 
 COLLECT (Nonius BV, 1997) 
;
_computing_data_reduction
; 
 Denzo/Scalepack (Otwinowski & Minor, 1996) 
;
_computing_molecular_graphics
; 
 CAMERON (Watkin et al 1996) 
;
_computing_publication_material
; 
 CRYSTALS (Watkin et al 2003) 
;
_computing_structure_refinement
; 
 CRYSTALS (Watkin et al 2003) 
;
_computing_structure_solution
; 
 SHELXS 86 (Sheldrick, 1986) 
;
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
; 
Nonius Kappa CCD 
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.10
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13476
_diffrn_reflns_theta_full        27.504
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         2.222
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
; 
 DIFABS (Walker & Stuart, 1983) 
;
_exptl_crystal_colour            ' ? '
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       ' block '
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0558
_refine_ls_number_parameters     272
_refine_ls_number_reflns         2285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.000128
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 1.20 1.24 0.875 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0674
_refine_ls_wR_factor_gt          0.0512
_refine_ls_wR_factor_ref         0.0512
_reflns_limit_h_max              23
_reflns_limit_h_min              -25
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              29
_reflns_limit_l_min              0
_reflns_number_gt                2285
_reflns_number_total             4372
_reflns_threshold_expression     I>3.00u(I)
_cod_data_source_file            jo800707q-File002.cif
_cod_data_source_block           CRYSTALS_cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

2020-10-09
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         194.07
_cod_original_formula_moiety         ' C10.35 H9.41 O3.76 '
_cod_original_formula_units_Z            17
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_original_formula_sum        ' C10.35 H9.41 O3.76 '
_cod_database_code               4023578
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
x+1/2,-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C -0.10602(13) 0.3097(2) -0.02870(10) 0.0305 1.0000 Uani . . . . . .
C2 C -0.03688(12) 0.2562(2) 0.00867(10) 0.0276 1.0000 Uani . . . . . .
C3 C -0.00752(11) 0.2697(2) 0.07606(10) 0.0272 1.0000 Uani . . . . . .
C4 C -0.05007(12) 0.3353(3) 0.10403(10) 0.0323 1.0000 Uani . . . . . .
C5 C -0.11802(13) 0.3920(3) 0.06792(11) 0.0361 1.0000 Uani . . . . . .
C6 C -0.14656(13) 0.3803(3) 0.00082(11) 0.0358 1.0000 Uani . . . . . .
C7 C -0.18756(16) 0.1880(3) -0.11989(13) 0.0506 1.0000 Uani . . . . . .
C8 C 0.03798(18) 0.2790(4) -0.04946(15) 0.0579 1.0000 Uani . . . . . .
C9 C -0.2553(2) 0.5101(5) -0.01434(16) 0.0782 1.0000 Uani . . . . . .
C10 C 0.06967(12) 0.2162(2) 0.11451(10) 0.0284 1.0000 Uani . . . . . .
C11 C 0.12496(12) 0.3392(2) 0.13164(10) 0.0307 1.0000 Uani . . . . . .
C12 C 0.13037(13) 0.4350(2) 0.18873(11) 0.0331 1.0000 Uani . . . . . .
C13 C 0.11515(14) 0.3568(3) 0.24162(11) 0.0346 1.0000 Uani . . . . . .
C14 C 0.10018(12) 0.2009(2) 0.23535(10) 0.0270 1.0000 Uani . . . . . .
C15 C 0.07847(11) 0.1324(2) 0.17511(10) 0.0264 1.0000 Uani . . . . . .
C16 C 0.20217(13) 0.2808(3) 0.15195(12) 0.0412 1.0000 Uani . . . . . .
C17 C 0.21065(15) 0.4795(3) 0.21466(12) 0.0453 1.0000 Uani . . . . . .
C18 C 0.06643(12) -0.0164(2) 0.17019(10) 0.0292 1.0000 Uani . . . . . .
C19 C 0.07784(12) -0.0894(2) 0.22639(11) 0.0282 1.0000 Uani . . . . . .
C20 C 0.09855(12) -0.0207(2) 0.28578(10) 0.0266 1.0000 Uani . . . . . .
C21 C 0.10957(13) 0.1229(2) 0.29218(10) 0.0297 1.0000 Uani . . . . . .
C22 C 0.09802(13) -0.2589(3) 0.30256(12) 0.0365 1.0000 Uani . . . . . .
O1 O -0.13239(9) 0.29526(19) -0.09467(7) 0.0392 1.0000 Uani . . . . . .
O2 O 0.00160(9) 0.18610(19) -0.02166(7) 0.0364 1.0000 Uani . . . . . .
O3 O -0.21168(11) 0.4351(2) -0.04067(9) 0.0537 1.0000 Uani . . . . . .
O4 O 0.24849(10) 0.3584(2) 0.20171(9) 0.0499 1.0000 Uani . . . . . .
O5 O 0.22165(11) 0.1815(3) 0.12955(11) 0.0620 1.0000 Uani . . . . . .
O6 O 0.12006(15) 0.4227(2) 0.28949(10) 0.0625 1.0000 Uani . . . . . .
O7 O 0.10591(10) -0.12105(17) 0.33281(8) 0.0379 1.0000 Uani . . . . . .
O8 O 0.07318(10) -0.23423(17) 0.23388(8) 0.0396 1.0000 Uani . . . . . .
H41 H -0.0308 0.3414 0.1529 0.057(2) 1.0000 Uiso . . . . . .
H51 H -0.1465 0.4441 0.0903 0.057(2) 1.0000 Uiso . . . . . .
H71 H -0.2043 0.1828 -0.1681 0.057(2) 1.0000 Uiso . . . . . .
H72 H -0.2299 0.2130 -0.1086 0.057(2) 1.0000 Uiso . . . . . .
H73 H -0.1677 0.0915 -0.1007 0.057(2) 1.0000 Uiso . . . . . .
H81 H 0.0650 0.2187 -0.0711 0.057(2) 1.0000 Uiso . . . . . .
H82 H 0.0025 0.3421 -0.0835 0.057(2) 1.0000 Uiso . . . . . .
H83 H 0.0748 0.3402 -0.0157 0.057(2) 1.0000 Uiso . . . . . .
H91 H -0.3013 0.5475 -0.0489 0.057(2) 1.0000 Uiso . . . . . .
H92 H -0.2271 0.5990 0.0112 0.057(2) 1.0000 Uiso . . . . . .
H93 H -0.2677 0.4495 0.0166 0.057(2) 1.0000 Uiso . . . . . .
H101 H 0.0802 0.1456 0.0848 0.057(2) 1.0000 Uiso . . . . . .
H111 H 0.1066 0.3997 0.0908 0.057(2) 1.0000 Uiso . . . . . .
H121 H 0.0930 0.5160 0.1750 0.057(2) 1.0000 Uiso . . . . . .
H171 H 0.2298 0.4994 0.2623 0.057(2) 1.0000 Uiso . . . . . .
H172 H 0.2177 0.5681 0.1919 0.057(2) 1.0000 Uiso . . . . . .
H181 H 0.0510 -0.0682 0.1275 0.057(2) 1.0000 Uiso . . . . . .
H211 H 0.1235 0.1724 0.3356 0.057(2) 1.0000 Uiso . . . . . .
H221 H 0.0611 -0.3194 0.3125 0.057(2) 1.0000 Uiso . . . . . .
H222 H 0.1457 -0.3127 0.3194 0.057(2) 1.0000 Uiso . . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C   ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H   ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 International_Tables_Vol_IV_Table_2.2B
'O   ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 International_Tables_Vol_IV_Table_2.2B
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C1 . C6 . 120.9(2) yes
O1 . C1 . C2 . 118.9(2) yes
C6 . C1 . C2 . 120.14(19) yes
O2 . C2 . C3 . 120.17(19) yes
O2 . C2 . C1 . 118.89(19) yes
C3 . C2 . C1 . 120.9(2) yes
C10 . C3 . C4 . 123.45(18) yes
C10 . C3 . C2 . 118.96(19) yes
C4 . C3 . C2 . 117.6(2) yes
H41 . C4 . C5 . 118.804 no
H41 . C4 . C3 . 118.683 no
C5 . C4 . C3 . 122.5(2) yes
H51 . C5 . C6 . 120.269 no
H51 . C5 . C4 . 120.019 no
C6 . C5 . C4 . 119.7(2) yes
O3 . C6 . C5 . 125.8(2) yes
O3 . C6 . C1 . 115.1(2) yes
C5 . C6 . C1 . 119.1(2) yes
H73 . C7 . H72 . 109.101 no
H73 . C7 . H71 . 109.169 no
H72 . C7 . H71 . 109.362 no
H73 . C7 . O1 . 109.785 no
H72 . C7 . O1 . 109.546 no
H71 . C7 . O1 . 109.860 no
H83 . C8 . H82 . 109.580 no
H83 . C8 . H81 . 107.732 no
H82 . C8 . H81 . 107.564 no
H83 . C8 . O2 . 111.132 no
H82 . C8 . O2 . 111.142 no
H81 . C8 . O2 . 109.564 no
H93 . C9 . H92 . 106.904 no
H93 . C9 . H91 . 109.490 no
H92 . C9 . H91 . 106.613 no
H93 . C9 . O3 . 112.212 no
H92 . C9 . O3 . 109.516 no
H91 . C9 . O3 . 111.834 no
H101 . C10 . C15 . 106.242 no
H101 . C10 . C11 . 109.384 no
C15 . C10 . C11 . 109.86(17) yes
H101 . C10 . C3 . 105.214 no
C15 . C10 . C3 . 114.20(17) yes
C11 . C10 . C3 . 111.61(18) yes
H111 . C11 . C16 . 115.456 no
H111 . C11 . C12 . 108.679 no
C16 . C11 . C12 . 103.09(18) yes
H111 . C11 . C10 . 102.585 no
C16 . C11 . C10 . 110.8(2) yes
C12 . C11 . C10 . 116.76(18) yes
H121 . C12 . C17 . 116.663 no
H121 . C12 . C13 . 104.005 no
C17 . C12 . C13 . 109.40(19) yes
H121 . C12 . C11 . 111.876 no
C17 . C12 . C11 . 101.1(2) yes
C13 . C12 . C11 . 114.16(19) yes
O6 . C13 . C14 . 121.6(2) yes
O6 . C13 . C12 . 118.9(2) yes
C14 . C13 . C12 . 119.3(2) yes
C21 . C14 . C15 . 121.4(2) yes
C21 . C14 . C13 . 117.77(19) yes
C15 . C14 . C13 . 120.78(19) yes
C18 . C15 . C14 . 120.13(19) yes
C18 . C15 . C10 . 118.62(18) yes
C14 . C15 . C10 . 121.2(2) yes
O5 . C16 . O4 . 122.4(2) yes
O5 . C16 . C11 . 127.6(2) yes
O4 . C16 . C11 . 109.9(2) yes
H172 . C17 . H171 . 108.756 no
H172 . C17 . O4 . 109.992 no
H171 . C17 . O4 . 110.420 no
H172 . C17 . C12 . 111.232 no
H171 . C17 . C12 . 111.010 no
O4 . C17 . C12 . 105.4(2) yes
H181 . C18 . C19 . 121.377 no
H181 . C18 . C15 . 121.617 no
C19 . C18 . C15 . 116.99(19) yes
O8 . C19 . C20 . 110.04(19) yes
O8 . C19 . C18 . 127.4(2) yes
C20 . C19 . C18 . 122.6(2) yes
O7 . C20 . C21 . 128.6(2) yes
O7 . C20 . C19 . 109.35(19) yes
C21 . C20 . C19 . 122.0(2) yes
H211 . C21 . C20 . 121.458 no
H211 . C21 . C14 . 121.749 no
C20 . C21 . C14 . 116.79(19) yes
H222 . C22 . H221 . 107.638 no
H222 . C22 . O8 . 110.853 no
H221 . C22 . O8 . 110.412 no
H222 . C22 . O7 . 110.767 no
H221 . C22 . O7 . 110.032 no
O8 . C22 . O7 . 107.16(17) yes
C1 . O1 . C7 . 113.91(19) yes
C2 . O2 . C8 . 114.4(2) yes
C6 . O3 . C9 . 118.3(2) yes
C16 . O4 . C17 . 109.94(19) yes
C20 . O7 . C22 . 106.36(17) yes
C19 . O8 . C22 . 106.12(17) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . O1 . 1.370(3) yes
C1 . C6 . 1.395(4) yes
C1 . C2 . 1.393(3) yes
C2 . O2 . 1.374(3) yes
C2 . C3 . 1.398(3) yes
C3 . C10 . 1.521(3) yes
C3 . C4 . 1.381(3) yes
C4 . H41 . 1.013 no
C4 . C5 . 1.380(3) yes
C5 . H51 . 1.017 no
C5 . C6 . 1.390(3) yes
C6 . O3 . 1.363(3) yes
C7 . H73 . 1.004 no
C7 . H72 . 1.001 no
C7 . H71 . 1.000 no
C7 . O1 . 1.425(3) yes
C8 . H83 . 0.998 no
C8 . H82 . 1.000 no
C8 . H81 . 1.024 no
C8 . O2 . 1.420(3) yes
C9 . H93 . 0.998 no
C9 . H92 . 1.035 no
C9 . H91 . 1.002 no
C9 . O3 . 1.413(4) yes
C10 . H101 . 1.013 no
C10 . C15 . 1.517(3) yes
C10 . C11 . 1.527(3) yes
C11 . H111 . 1.013 no
C11 . C16 . 1.523(3) yes
C11 . C12 . 1.529(3) yes
C12 . H121 . 1.016 no
C12 . C17 . 1.529(4) yes
C12 . C13 . 1.522(3) yes
C13 . O6 . 1.207(3) yes
C13 . C14 . 1.470(3) yes
C14 . C21 . 1.415(3) yes
C14 . C15 . 1.400(3) yes
C15 . C18 . 1.397(3) yes
C16 . O5 . 1.186(3) yes
C16 . O4 . 1.344(3) yes
C17 . H172 . 1.007 no
C17 . H171 . 1.002 no
C17 . O4 . 1.444(4) yes
C18 . H181 . 1.008 no
C18 . C19 . 1.371(3) yes
C19 . O8 . 1.360(3) yes
C19 . C20 . 1.387(3) yes
C20 . O7 . 1.372(3) yes
C20 . C21 . 1.348(3) yes
C21 . H211 . 1.012 no
C22 . H222 . 1.005 no
C22 . H221 . 1.018 no
C22 . O8 . 1.441(3) yes
C22 . O7 . 1.427(3) yes
