#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/02/7150269.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_7150269
loop_
_publ_author_name
'Rodriguez, Raphaël'
'Moses, John E.'
'Adlington, Robert M.'
'Baldwin, Jack E.'
_publ_section_title
;
 A new and efficient method for o-quinone methide intermediate
 generation: application to the biomimetic synthesis of the benzopyran
 derived natural products (+/-)-lucidene and (+/-)-alboatrin.
;
_journal_issue                   19
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3488
_journal_page_last               3495
_journal_paper_doi               10.1039/b508972g
_journal_volume                  3
_journal_year                    2005
_chemical_compound_source
;
synthesis as described
;
_chemical_formula_moiety         ' C12 H14 O5 '
_chemical_formula_sum            'C12 H14 O5'
_chemical_formula_weight         238.24
_chemical_name_systematic
;
?
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 123.921(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.1890(14)
_cell_length_b                   4.9244(3)
_cell_length_c                   19.8157(11)
_cell_measurement_reflns_used    11482
_cell_measurement_temperature    150
_cell_measurement_theta_max      28
_cell_measurement_theta_min      5
_cell_volume                     2363.5(2)
_computing_cell_refinement
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_data_collection
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_publication_material
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_refinement
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
;
Nonius KappaCCD
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11482
_diffrn_reflns_theta_full        27.493
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         5.131
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       ' prism '
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0723
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1691
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max          0.008849
_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:
1.33 0.897 0.913
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0712
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0599
_reflns_limit_h_max              31
_reflns_limit_h_min              -37
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                1691
_reflns_number_total             2683
_reflns_threshold_expression     I>3.00u(I)
_cod_data_source_file            b508972g.txt
_cod_data_source_block           1
_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 
;
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_original_formula_sum        ' C12 H14 O5 '
_cod_database_code               7150269
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
C1 C 0.35363(8) 0.1802(4) 0.37123(11) 0.0294 1.0000 Uani
C2 C 0.32513(8) 0.0988(4) 0.29098(11) 0.0299 1.0000 Uani
C3 C 0.33895(8) 0.2235(4) 0.24146(11) 0.0302 1.0000 Uani
C4 C 0.38008(8) 0.4243(4) 0.27183(12) 0.0308 1.0000 Uani
C5 C 0.40819(8) 0.5005(4) 0.35391(12) 0.0305 1.0000 Uani
C6 C 0.39428(8) 0.3768(4) 0.40357(11) 0.0308 1.0000 Uani
O1 O 0.34334(6) 0.0438(3) 0.42424(8) 0.0324 1.0000 Uani
C7 C 0.30105(8) 0.1328(4) 0.42732(11) 0.0318 1.0000 Uani
O2 O 0.27200(7) 0.3177(4) 0.38532(10) 0.0483 1.0000 Uani
C8 C 0.29665(9) -0.0191(5) 0.48837(12) 0.0376 1.0000 Uani
O3 O 0.31369(6) 0.1549(3) 0.16156(8) 0.0396 1.0000 Uani
C9 C 0.39138(9) 0.5492(4) 0.21342(13) 0.0357 1.0000 Uani
O4 O 0.42440(6) 0.3561(3) 0.20183(8) 0.0366 1.0000 Uani
C10 C 0.42232(8) 0.3795(4) 0.13291(12) 0.0334 1.0000 Uani
O5 O 0.39649(9) 0.5544(3) 0.08334(10) 0.0519 1.0000 Uani
C11 C 0.45511(10) 0.1623(4) 0.12542(14) 0.0401 1.0000 Uani
C12 C 0.45299(9) 0.7129(4) 0.38966(14) 0.0390 1.0000 Uani
H1 H 0.2842(13) 0.035(6) 0.1431(18) 0.064(9) 1.0000 Uiso
H21 H 0.2958 -0.0438 0.2693 0.0361 1.0000 Uiso
H61 H 0.4136 0.4302 0.4620 0.0356 1.0000 Uiso
H81 H 0.2648 0.0527 0.4889 0.0465 1.0000 Uiso
H82 H 0.3315 0.0041 0.5435 0.0465 1.0000 Uiso
H83 H 0.2907 -0.2162 0.4738 0.0465 1.0000 Uiso
H91 H 0.4122 0.7230 0.2363 0.0443 1.0000 Uiso
H92 H 0.3558 0.5861 0.1603 0.0443 1.0000 Uiso
H111 H 0.4525 0.1867 0.0733 0.0498 1.0000 Uiso
H112 H 0.4946 0.1751 0.1722 0.0498 1.0000 Uiso
H113 H 0.4401 -0.0198 0.1257 0.0498 1.0000 Uiso
H121 H 0.4679 0.7383 0.4485 0.0447 1.0000 Uiso
H122 H 0.4834 0.6527 0.3840 0.0447 1.0000 Uiso
H123 H 0.4374 0.8885 0.3602 0.0447 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
C2 . C1 . C6 . 123.21(17) yes
C2 . C1 . O1 . 118.46(17) yes
C6 . C1 . O1 . 118.19(16) yes
C1 . C2 . C3 . 117.24(17) yes
C1 . C2 . H21 . 121.381 no
C3 . C2 . H21 . 121.381 no
C2 . C3 . C4 . 121.47(17) yes
C2 . C3 . O3 . 121.77(17) yes
C4 . C3 . O3 . 116.75(18) yes
C3 . C4 . C5 . 119.43(18) yes
C3 . C4 . C9 . 117.46(17) yes
C5 . C4 . C9 . 123.11(18) yes
C4 . C5 . C6 . 119.23(18) yes
C4 . C5 . C12 . 121.53(18) yes
C6 . C5 . C12 . 119.24(18) yes
C1 . C6 . C5 . 119.42(17) yes
C1 . C6 . H61 . 120.292 no
C5 . C6 . H61 . 120.292 no
C1 . O1 . C7 . 117.42(15) yes
O1 . C7 . O2 . 121.71(18) yes
O1 . C7 . C8 . 111.80(17) yes
O2 . C7 . C8 . 126.48(19) yes
C7 . C8 . H81 . 109.467 no
C7 . C8 . H82 . 109.467 no
H81 . C8 . H82 . 109.476 no
C7 . C8 . H83 . 109.466 no
H81 . C8 . H83 . 109.476 no
H82 . C8 . H83 . 109.476 no
C3 . O3 . H1 . 113.2(18) yes
C4 . C9 . O4 . 107.61(16) yes
C4 . C9 . H91 . 109.935 no
O4 . C9 . H91 . 109.935 no
C4 . C9 . H92 . 109.935 no
O4 . C9 . H92 . 109.935 no
H91 . C9 . H92 . 109.467 no
C9 . O4 . C10 . 116.52(15) yes
O4 . C10 . O5 . 123.1(2) yes
O4 . C10 . C11 . 111.88(17) yes
O5 . C10 . C11 . 125.05(19) yes
C10 . C11 . H111 . 109.467 no
C10 . C11 . H112 . 109.467 no
H111 . C11 . H112 . 109.476 no
C10 . C11 . H113 . 109.467 no
H111 . C11 . H113 . 109.476 no
H112 . C11 . H113 . 109.476 no
C5 . C12 . H121 . 109.467 no
C5 . C12 . H122 . 109.467 no
H121 . C12 . H122 . 109.476 no
C5 . C12 . H123 . 109.467 no
H121 . C12 . H123 . 109.476 no
H122 . C12 . H123 . 109.476 no
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 . C2 . 1.380(3) yes
C1 . C6 . 1.381(3) yes
C1 . O1 . 1.413(2) yes
C2 . C3 . 1.394(3) yes
C2 . H21 . 1.000 no
C3 . C4 . 1.406(3) yes
C3 . O3 . 1.364(2) yes
C4 . C5 . 1.404(3) yes
C4 . C9 . 1.501(3) yes
C5 . C6 . 1.396(3) yes
C5 . C12 . 1.507(3) yes
C6 . H61 . 1.000 no
O1 . C7 . 1.343(2) yes
C7 . O2 . 1.205(3) yes
C7 . C8 . 1.488(3) yes
C8 . H81 . 1.000 no
C8 . H82 . 1.000 no
C8 . H83 . 1.000 no
O3 . H1 . 0.94(3) yes
C9 . O4 . 1.461(3) yes
C9 . H91 . 1.000 no
C9 . H92 . 1.000 no
O4 . C10 . 1.338(2) yes
C10 . O5 . 1.204(3) yes
C10 . C11 . 1.497(3) yes
C11 . H111 . 1.000 no
C11 . H112 . 1.000 no
C11 . H113 . 1.000 no
C12 . H121 . 1.000 no
C12 . H122 . 1.000 no
C12 . H123 . 1.000 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H1 O2 7_545 0.94(3) 1.77(3) 2.699(2) 175(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21141217
