#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/09/7150987.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_7150987
loop_
_publ_author_name
'Jiang, Xuefeng'
'Kong, Wangqing'
'Chen, Jie'
'Ma, Shengming'
_publ_section_title
;
 Intermolecular sequential [4 + 2]-cycloaddition--aromatization
 reaction of aryl-substituted allenes with DMAD affording phenanthrene
 and naphthalene derivatives
;
_journal_issue                   19
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              3606
_journal_page_last               3610
_journal_paper_doi               10.1039/b808767a
_journal_volume                  6
_journal_year                    2008
_chemical_formula_sum            'C23 H22 O6'
_chemical_formula_weight         394.41
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.494(2)
_cell_angle_beta                 91.931(2)
_cell_angle_gamma                109.458(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7495(7)
_cell_length_b                   10.1805(9)
_cell_length_c                   13.3793(12)
_cell_measurement_reflns_used    2143
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.782
_cell_measurement_theta_min      5.426
_cell_volume                     991.77(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5856
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75789
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.448
_exptl_crystal_size_mid          0.357
_exptl_crystal_size_min          0.347
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0525
_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)+(0.0851P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1429
_refine_ls_wR_factor_ref         0.1539
_reflns_number_gt                2969
_reflns_number_total             4188
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b808767a.txt
_cod_data_source_block           cd2663
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               7150987
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.02012(17) -0.08327(15) 0.34462(9) 0.0642(4) Uani 1 1 d . . .
O2 O 0.30925(15) -0.02094(12) 0.40509(8) 0.0461(3) Uani 1 1 d . . .
O3 O 0.57543(17) 0.32002(14) 0.40962(9) 0.0568(4) Uani 1 1 d . . .
O4 O 0.27268(17) 0.24937(12) 0.42578(9) 0.0525(3) Uani 1 1 d . . .
O5 O 0.3915(3) 0.5694(2) 0.13012(15) 0.1009(8) Uani 1 1 d . . .
O6 O 0.3401(2) 0.51237(18) 0.28417(12) 0.0825(5) Uani 1 1 d . . .
C1 C 0.3511(3) 0.0783(2) -0.11341(13) 0.0529(5) Uani 1 1 d . . .
H1 H 0.4359 0.1681 -0.1035 0.063 Uiso 1 1 calc R . .
C2 C 0.3113(3) 0.0135(2) -0.20839(14) 0.0631(5) Uani 1 1 d . . .
H2 H 0.3702 0.0596 -0.2621 0.076 Uiso 1 1 calc R . .
C3 C 0.1843(3) -0.1199(2) -0.22532(14) 0.0671(6) Uani 1 1 d . . .
H3 H 0.1566 -0.1623 -0.2902 0.081 Uiso 1 1 calc R . .
C4 C 0.1005(3) -0.1885(2) -0.14699(14) 0.0592(5) Uani 1 1 d . . .
H4 H 0.0147 -0.2777 -0.1588 0.071 Uiso 1 1 calc R . .
C5 C 0.1412(2) -0.12684(18) -0.04809(12) 0.0451(4) Uani 1 1 d . . .
C6 C 0.2655(2) 0.01053(18) -0.03091(11) 0.0404(4) Uani 1 1 d . . .
C7 C 0.2995(2) 0.07529(16) 0.07134(11) 0.0375(4) Uani 1 1 d . . .
C8 C 0.2171(2) -0.00234(16) 0.15149(11) 0.0371(4) Uani 1 1 d . . .
C9 C 0.0966(2) -0.14353(18) 0.12971(13) 0.0480(4) Uani 1 1 d . . .
H9 H 0.0433 -0.1962 0.1820 0.058 Uiso 1 1 calc R . .
C10 C 0.0599(3) -0.20047(19) 0.03500(14) 0.0542(5) Uani 1 1 d . . .
H10 H -0.0215 -0.2913 0.0232 0.065 Uiso 1 1 calc R . .
C11 C 0.2590(2) 0.06183(16) 0.25059(11) 0.0365(4) Uani 1 1 d . . .
C12 C 0.3734(2) 0.19927(16) 0.26903(11) 0.0363(4) Uani 1 1 d . . .
C13 C 0.4476(2) 0.27927(16) 0.18814(12) 0.0388(4) Uani 1 1 d . . .
C14 C 0.4096(2) 0.21556(17) 0.09241(12) 0.0413(4) Uani 1 1 d . . .
H14 H 0.4592 0.2678 0.0393 0.050 Uiso 1 1 calc R . .
C15 C 0.1792(2) -0.02184(17) 0.33656(12) 0.0403(4) Uani 1 1 d . . .
C16 C 0.2427(3) -0.0842(2) 0.49718(13) 0.0594(5) Uani 1 1 d . . .
H16A H 0.1630 -0.0395 0.5263 0.089 Uiso 1 1 calc R . .
H16B H 0.3447 -0.0729 0.5436 0.089 Uiso 1 1 calc R . .
H16C H 0.1763 -0.1819 0.4824 0.089 Uiso 1 1 calc R . .
C17 C 0.4213(2) 0.26298(17) 0.37458(12) 0.0416(4) Uani 1 1 d . . .
C18 C 0.3079(3) 0.3028(2) 0.52996(15) 0.0758(7) Uani 1 1 d . . .
H18A H 0.3933 0.2661 0.5615 0.114 Uiso 1 1 calc R . .
H18B H 0.1953 0.2748 0.5635 0.114 Uiso 1 1 calc R . .
H18C H 0.3585 0.4029 0.5339 0.114 Uiso 1 1 calc R . .
C19 C 0.5571(2) 0.43522(18) 0.20436(14) 0.0478(4) Uani 1 1 d . . .
C20 C 0.7043(3) 0.4879(2) 0.12968(17) 0.0734(6) Uani 1 1 d . . .
H20A H 0.6471 0.4847 0.0644 0.110 Uiso 1 1 calc R . .
H20B H 0.7797 0.4298 0.1273 0.110 Uiso 1 1 calc R . .
H20C H 0.7787 0.5824 0.1503 0.110 Uiso 1 1 calc R . .
C21 C 0.4240(3) 0.51452(19) 0.20125(15) 0.0584(5) Uani 1 1 d . . .
C22 C 0.2044(4) 0.5826(4) 0.2888(3) 0.1104(10) Uani 1 1 d . . .
H22A H 0.2651 0.6819 0.3050 0.122 Uiso 1 1 calc R . .
H22B H 0.1384 0.5699 0.2240 0.122 Uiso 1 1 calc R . .
C23 C 0.0797(4) 0.5264(4) 0.3629(3) 0.1114(12) Uani 1 1 d . . .
H23A H 0.0212 0.4278 0.3471 0.132 Uiso 1 1 calc R . .
H23B H -0.0114 0.5712 0.3647 0.132 Uiso 1 1 calc R . .
H23C H 0.1448 0.5420 0.4273 0.132 Uiso 1 1 calc R . .
H19 H 0.615(2) 0.4513(19) 0.2721(14) 0.052(5) 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O2 C16 115.29(13) . . ?
C17 O4 C18 115.28(14) . . ?
C21 O6 C22 117.5(2) . . ?
C2 C1 C6 120.79(18) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C1 C2 C3 120.77(18) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 119.78(17) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.11(19) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 119.29(17) . . ?
C4 C5 C10 121.45(17) . . ?
C6 C5 C10 119.26(15) . . ?
C1 C6 C5 118.19(15) . . ?
C1 C6 C7 123.19(15) . . ?
C5 C6 C7 118.62(14) . . ?
C14 C7 C8 118.55(14) . . ?
C14 C7 C6 121.43(14) . . ?
C8 C7 C6 120.00(14) . . ?
C7 C8 C11 118.62(14) . . ?
C7 C8 C9 118.76(14) . . ?
C11 C8 C9 122.61(14) . . ?
C10 C9 C8 120.87(16) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C5 122.36(16) . . ?
C9 C10 H10 118.8 . . ?
C5 C10 H10 118.8 . . ?
C12 C11 C8 121.23(14) . . ?
C12 C11 C15 119.74(13) . . ?
C8 C11 C15 119.02(13) . . ?
C11 C12 C13 120.01(14) . . ?
C11 C12 C17 120.20(13) . . ?
C13 C12 C17 119.78(13) . . ?
C14 C13 C12 118.46(14) . . ?
C14 C13 C19 119.86(14) . . ?
C12 C13 C19 121.57(14) . . ?
C13 C14 C7 122.99(14) . . ?
C13 C14 H14 118.5 . . ?
C7 C14 H14 118.5 . . ?
O1 C15 O2 122.86(15) . . ?
O1 C15 C11 125.52(15) . . ?
O2 C15 C11 111.62(13) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 O4 123.57(15) . . ?
O3 C17 C12 124.42(15) . . ?
O4 C17 C12 112.01(14) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C19 C20 110.56(17) . . ?
C21 C19 C13 108.12(14) . . ?
C20 C19 C13 114.28(15) . . ?
C21 C19 H19 107.6(10) . . ?
C20 C19 H19 109.0(11) . . ?
C13 C19 H19 107.0(11) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C21 O6 122.5(2) . . ?
O5 C21 C19 124.7(2) . . ?
O6 C21 C19 112.67(17) . . ?
C23 C22 O6 109.6(3) . . ?
C23 C22 H22A 109.7 . . ?
O6 C22 H22A 109.7 . . ?
C23 C22 H22B 109.7 . . ?
O6 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
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
O1 C15 1.1942(19) . ?
O2 C15 1.3367(19) . ?
O2 C16 1.455(2) . ?
O3 C17 1.205(2) . ?
O4 C17 1.331(2) . ?
O4 C18 1.448(2) . ?
O5 C21 1.193(2) . ?
O6 C21 1.302(2) . ?
O6 C22 1.457(3) . ?
C1 C2 1.371(3) . ?
C1 C6 1.404(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.356(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.408(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.409(2) . ?
C5 C10 1.424(2) . ?
C6 C7 1.458(2) . ?
C7 C14 1.404(2) . ?
C7 C8 1.413(2) . ?
C8 C11 1.419(2) . ?
C8 C9 1.435(2) . ?
C9 C10 1.341(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.386(2) . ?
C11 C15 1.499(2) . ?
C12 C13 1.415(2) . ?
C12 C17 1.498(2) . ?
C13 C14 1.376(2) . ?
C13 C19 1.528(2) . ?
C14 H14 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C21 1.508(3) . ?
C19 C20 1.524(3) . ?
C19 H19 0.977(18) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C22 C23 1.419(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 2.7(3) . . . . ?
C3 C4 C5 C10 -177.19(18) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
C2 C1 C6 C7 -178.64(16) . . . . ?
C4 C5 C6 C1 -3.2(2) . . . . ?
C10 C5 C6 C1 176.70(15) . . . . ?
C4 C5 C6 C7 177.07(15) . . . . ?
C10 C5 C6 C7 -3.1(2) . . . . ?
C1 C6 C7 C14 5.6(2) . . . . ?
C5 C6 C7 C14 -174.62(15) . . . . ?
C1 C6 C7 C8 -176.01(15) . . . . ?
C5 C6 C7 C8 3.7(2) . . . . ?
C14 C7 C8 C11 -4.2(2) . . . . ?
C6 C7 C8 C11 177.37(13) . . . . ?
C14 C7 C8 C9 176.74(14) . . . . ?
C6 C7 C8 C9 -1.7(2) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
C11 C8 C9 C10 179.86(16) . . . . ?
C8 C9 C10 C5 1.9(3) . . . . ?
C4 C5 C10 C9 -179.83(18) . . . . ?
C6 C5 C10 C9 0.3(3) . . . . ?
C7 C8 C11 C12 2.1(2) . . . . ?
C9 C8 C11 C12 -178.86(15) . . . . ?
C7 C8 C11 C15 -177.18(14) . . . . ?
C9 C8 C11 C15 1.8(2) . . . . ?
C8 C11 C12 C13 1.4(2) . . . . ?
C15 C11 C12 C13 -179.29(14) . . . . ?
C8 C11 C12 C17 -177.71(14) . . . . ?
C15 C11 C12 C17 1.6(2) . . . . ?
C11 C12 C13 C14 -2.8(2) . . . . ?
C17 C12 C13 C14 176.35(14) . . . . ?
C11 C12 C13 C19 173.29(15) . . . . ?
C17 C12 C13 C19 -7.6(2) . . . . ?
C12 C13 C14 C7 0.6(2) . . . . ?
C19 C13 C14 C7 -175.54(15) . . . . ?
C8 C7 C14 C13 2.9(2) . . . . ?
C6 C7 C14 C13 -178.67(14) . . . . ?
C16 O2 C15 O1 -8.0(2) . . . . ?
C16 O2 C15 C11 172.35(13) . . . . ?
C12 C11 C15 O1 126.61(19) . . . . ?
C8 C11 C15 O1 -54.1(2) . . . . ?
C12 C11 C15 O2 -53.74(19) . . . . ?
C8 C11 C15 O2 125.60(15) . . . . ?
C18 O4 C17 O3 -2.8(2) . . . . ?
C18 O4 C17 C12 177.29(15) . . . . ?
C11 C12 C17 O3 126.71(18) . . . . ?
C13 C12 C17 O3 -52.4(2) . . . . ?
C11 C12 C17 O4 -53.33(19) . . . . ?
C13 C12 C17 O4 127.57(15) . . . . ?
C14 C13 C19 C21 89.09(18) . . . . ?
C12 C13 C19 C21 -86.91(19) . . . . ?
C14 C13 C19 C20 -34.5(2) . . . . ?
C12 C13 C19 C20 149.52(17) . . . . ?
C22 O6 C21 O5 -1.1(4) . . . . ?
C22 O6 C21 C19 -178.4(2) . . . . ?
C20 C19 C21 O5 26.4(3) . . . . ?
C13 C19 C21 O5 -99.4(3) . . . . ?
C20 C19 C21 O6 -156.39(17) . . . . ?
C13 C19 C21 O6 77.8(2) . . . . ?
C21 O6 C22 C23 157.2(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25938849
