#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:51:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180319 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/33/7153324.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_7153324
loop_
_publ_author_name
'Salame, Rim'
'Gravel, Edmond'
'Retailleau, Pascal'
'Poupon, Erwan'
_publ_section_title
;
 Biomimetically relevant self-condensations of C5 units derived from
 lysine.
;
_journal_issue                   11
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2522
_journal_page_last               2528
_journal_paper_doi               10.1039/b926786g
_journal_volume                  8
_journal_year                    2010
_chemical_formula_moiety         'C10 H12 O2'
_chemical_formula_sum            'C10 H12 O2'
_chemical_formula_weight         164.20
_chemical_name_common            (2Z,6Z)-cycloocta-2,6-diene-1,5-dicarbaldehyde
_chemical_name_systematic
;
(2Z,6Z)-cycloocta-2,6-diene-1,5-dicarbaldehyde
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.312(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.160(4)
_cell_length_b                   13.956(5)
_cell_length_c                   8.879(4)
_cell_measurement_reflns_used    1779
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.022
_cell_measurement_theta_min      0.407
_cell_volume                     870.0(7)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11473
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0471
_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)+(0.0677P)²+0.1069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1288
_reflns_number_gt                1204
_reflns_number_total             1701
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b926786g.txt
_cod_data_source_block           compound_18_CCDC_753049
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7153324
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.13266(18) 0.02346(12) 0.22808(16) 0.0803(5) Uani 1 1 d .
O2 O 0.82861(19) 0.38640(11) 0.08390(16) 0.0732(4) Uani 1 1 d .
C1 C 0.3904(2) 0.08862(11) 0.12981(17) 0.0431(4) Uani 1 1 d .
C2 C 0.2592(2) 0.12621(12) -0.01115(19) 0.0483(4) Uani 1 1 d .
H2A H 0.1446 0.0874 -0.0308 0.058 Uiso 1 1 calc R
H2B H 0.3210 0.1195 -0.0985 0.058 Uiso 1 1 calc R
C3 C 0.2035(2) 0.23061(13) 0.0023(2) 0.0557(5) Uani 1 1 d .
H3A H 0.1203 0.2486 -0.0934 0.067 Uiso 1 1 calc R
H3B H 0.1290 0.2347 0.0823 0.067 Uiso 1 1 calc R
C4 C 0.3578(2) 0.30349(12) 0.03615(19) 0.0495(4) Uani 1 1 d .
H4 H 0.3225 0.3611 0.0752 0.059 Uiso 1 1 calc R
C5 C 0.5396(2) 0.29939(11) 0.01935(18) 0.0443(4) Uani 1 1 d .
C6 C 0.6383(2) 0.21740(13) -0.04139(19) 0.0508(4) Uani 1 1 d .
H6A H 0.7422 0.2420 -0.0857 0.061 Uiso 1 1 calc R
H6B H 0.5493 0.1855 -0.1223 0.061 Uiso 1 1 calc R
C7 C 0.7168(2) 0.14483(13) 0.0837(2) 0.0547(5) Uani 1 1 d .
H7A H 0.7826 0.0954 0.0377 0.066 Uiso 1 1 calc R
H7B H 0.8113 0.1772 0.1599 0.066 Uiso 1 1 calc R
C8 C 0.5798(2) 0.09678(12) 0.16540(19) 0.0477(4) Uani 1 1 d .
H8 H 0.6359 0.0673 0.2571 0.057 Uiso 1 1 calc R
C9 C 0.3016(3) 0.03716(14) 0.2407(2) 0.0568(5) Uani 1 1 d .
H9 H 0.3814 0.0131 0.3278 0.068 Uiso 1 1 calc R
C10 C 0.6579(3) 0.38206(13) 0.0762(2) 0.0565(5) Uani 1 1 d .
H10 H 0.5979 0.4351 0.1088 0.068 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0601(9) 0.0993(12) 0.0837(10) 0.0246(8) 0.0200(7) -0.0113(7)
O2 0.0613(9) 0.0778(10) 0.0778(10) -0.0074(7) 0.0071(7) -0.0233(7)
C1 0.0425(8) 0.0402(9) 0.0458(9) -0.0039(7) 0.0070(6) 0.0000(6)
C2 0.0390(8) 0.0556(11) 0.0483(9) 0.0008(8) 0.0038(7) -0.0074(7)
C3 0.0376(8) 0.0653(12) 0.0636(11) 0.0122(9) 0.0081(7) 0.0047(8)
C4 0.0498(9) 0.0475(10) 0.0510(10) 0.0055(8) 0.0091(7) 0.0086(7)
C5 0.0458(8) 0.0458(9) 0.0406(8) 0.0042(7) 0.0068(6) -0.0009(7)
C6 0.0417(8) 0.0616(11) 0.0521(10) -0.0086(8) 0.0165(7) -0.0068(7)
C7 0.0361(8) 0.0529(11) 0.0749(12) -0.0082(9) 0.0107(7) 0.0038(7)
C8 0.0452(9) 0.0438(9) 0.0519(9) -0.0032(7) 0.0037(7) 0.0069(7)
C9 0.0565(11) 0.0590(12) 0.0551(11) 0.0080(9) 0.0113(8) 0.0026(8)
C10 0.0628(12) 0.0517(11) 0.0536(10) 0.0036(8) 0.0080(8) -0.0054(8)
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
C8 C1 C9 116.00(15)
C8 C1 C2 127.33(15)
C9 C1 C2 116.67(14)
C1 C2 C3 113.53(14)
C1 C2 H2A 108.9
C3 C2 H2A 108.9
C1 C2 H2B 108.9
C3 C2 H2B 108.9
H2A C2 H2B 107.7
C4 C3 C2 118.34(13)
C4 C3 H3A 107.7
C2 C3 H3A 107.7
C4 C3 H3B 107.7
C2 C3 H3B 107.7
H3A C3 H3B 107.1
C5 C4 C3 130.32(16)
C5 C4 H4 114.8
C3 C4 H4 114.8
C4 C5 C10 115.95(16)
C4 C5 C6 127.54(15)
C10 C5 C6 116.38(14)
C5 C6 C7 112.13(14)
C5 C6 H6A 109.2
C7 C6 H6A 109.2
C5 C6 H6B 109.2
C7 C6 H6B 109.2
H6A C6 H6B 107.9
C8 C7 C6 118.04(13)
C8 C7 H7A 107.8
C6 C7 H7A 107.8
C8 C7 H7B 107.8
C6 C7 H7B 107.8
H7A C7 H7B 107.1
C1 C8 C7 131.16(16)
C1 C8 H8 114.4
C7 C8 H8 114.4
O1 C9 C1 125.15(16)
O1 C9 H9 117.4
C1 C9 H9 117.4
O2 C10 C5 124.65(17)
O2 C10 H10 117.7
C5 C10 H10 117.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.208(2)
O2 C10 1.212(2)
C1 C8 1.336(2)
C1 C9 1.461(2)
C1 C2 1.504(2)
C2 C3 1.521(2)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.488(2)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.340(2)
C4 H4 0.9300
C5 C10 1.461(2)
C5 C6 1.500(2)
C6 C7 1.526(3)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C8 1.489(2)
C7 H7A 0.9700
C7 H7B 0.9700
C8 H8 0.9300
C9 H9 0.9300
C10 H10 0.9300
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
C8 C1 C2 C3 -84.3(2)
C9 C1 C2 C3 95.83(17)
C1 C2 C3 C4 57.2(2)
C2 C3 C4 C5 19.7(3)
C3 C4 C5 C10 -175.15(16)
C3 C4 C5 C6 0.5(3)
C4 C5 C6 C7 -85.7(2)
C10 C5 C6 C7 89.98(17)
C5 C6 C7 C8 59.8(2)
C9 C1 C8 C7 -178.76(17)
C2 C1 C8 C7 1.4(3)
C6 C7 C8 C1 16.7(3)
C8 C1 C9 O1 179.49(18)
C2 C1 C9 O1 -0.6(3)
C4 C5 C10 O2 172.50(17)
C6 C5 C10 O2 -3.7(3)
