#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/15/2011569.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2011569
loop_
_publ_author_name
'Bolte, Michael'
'Degen, Alexander'
'Egert, Ernst'
_publ_section_title
;
 Diels--Alder adducts of maleic anhydride and dienes: new compounds by
 crystallization
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1338
_journal_page_last               1342
_journal_paper_doi               10.1107/S0108270100010131
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C9 H8 O3'
_chemical_formula_sum            'C9 H8 O3'
_chemical_formula_weight         164.15
_chemical_name_systematic
;
bicyclo[2.2.1]hept-2-ene-endo-cis-5,6-dicarboxylic anhydride
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.926(2)
_cell_length_b                   9.489(3)
_cell_length_c                   13.452(5)
_cell_measurement_reflns_used    7065
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1
_cell_volume                     756.4(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens CCD three-circle'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .037
_diffrn_reflns_av_sigmaI/netI    .012
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20569
_diffrn_reflns_theta_full        28.69
_diffrn_reflns_theta_max         28.69
_diffrn_reflns_theta_min         2.63
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  1440
_diffrn_standards_number         260
_exptl_absorpt_coefficient_mu    .109
_exptl_absorpt_correction_T_max  .981
_exptl_absorpt_correction_T_min  .948
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          .50
_exptl_crystal_size_mid          .40
_exptl_crystal_size_min          .18
_refine_diff_density_max         .35
_refine_diff_density_min         -.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1155
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          .043
_refine_ls_R_factor_gt           .041
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0826P)²+0.0338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .110
_reflns_number_gt                1082
_reflns_number_total             1155
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1412.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2011569
_cod_database_fobs_code          2011569
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 .4506(3) .38619(15) .38354(11) .0212(3) Uani d . 1 . . C
H1 .5270 .2939 .3711 .025 Uiso calc R 1 . . H
C2 .5923(3) .48059(15) .45206(11) .0208(3) Uani d . 1 . . C
H2 .7326 .4316 .4748 .025 Uiso calc R 1 . . H
C3 .6486(3) .61180(17) .38476(12) .0253(3) Uani d . 1 . . C
H3 .7792 .6711 .4063 .030 Uiso calc R 1 . . H
C4 .4273(4) .68864(17) .36767(13) .0296(4) Uani d . 1 . . C
H4 .3874 .7782 .3939 .036 Uiso calc R 1 . . H
C5 .2991(3) .60833(18) .30933(13) .0288(4) Uani d . 1 . . C
H5 .1512 .6301 .2869 .035 Uiso calc R 1 . . H
C6 .4315(3) .47574(16) .28505(12) .0249(3) Uani d . 1 . . C
H6 .3831 .4233 .2242 .030 Uiso calc R 1 . . H
C7 .6743(3) .53521(18) .28384(12) .0265(3) Uani d . 1 . . C
H7A .7016 .6007 .2278 .032 Uiso calc R 1 . . H
H7B .7910 .4606 .2851 .032 Uiso calc R 1 . . H
C8 .2314(3) .36648(16) .43786(13) .0246(3) Uani d . 1 . . C
C9 .4384(3) .51363(17) .53771(12) .0240(3) Uani d . 1 . . C
O1 .2306(2) .44609(13) .52451(9) .0276(3) Uani d . 1 . . O
O2 .0700(2) .29646(14) .41689(11) .0351(3) Uani d . 1 . . O
O3 .4683(3) .58680(15) .60864(9) .0352(4) Uani d . 1 . . O
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 .0238(7) .0111(6) .0286(7) .0008(5) .0015(6) -.0004(5)
C2 .0217(7) .0156(6) .0251(7) .0004(6) .0012(6) .0006(5)
C3 .0279(8) .0194(7) .0288(7) -.0065(6) .0042(6) .0000(6)
C4 .0385(10) .0154(7) .0351(8) .0044(7) .0124(8) .0065(6)
C5 .0270(8) .0252(8) .0342(8) .0058(7) .0039(7) .0109(6)
C6 .0269(8) .0225(7) .0253(7) .0011(7) -.0010(6) .0003(6)
C7 .0272(8) .0258(8) .0266(7) .0007(7) .0068(6) .0017(6)
C8 .0251(8) .0142(6) .0345(8) .0009(6) .0010(6) .0050(6)
C9 .0278(8) .0184(7) .0258(7) .0022(6) .0023(6) .0044(5)
O1 .0265(6) .0230(6) .0332(6) .0026(5) .0080(5) .0030(5)
O2 .0273(6) .0241(6) .0540(8) -.0065(6) -.0022(6) .0069(6)
O3 .0490(9) .0299(7) .0267(6) .0018(6) .0042(5) -.0042(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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 C2 104.69(13)
C8 C1 C6 114.41(14)
C2 C1 C6 103.24(12)
C8 C1 H1 111.3
C2 C1 H1 111.3
C6 C1 H1 111.3
C9 C2 C1 104.48(13)
C9 C2 C3 113.84(13)
C1 C2 C3 103.41(12)
C9 C2 H2 111.5
C1 C2 H2 111.5
C3 C2 H2 111.5
C4 C3 C7 100.25(14)
C4 C3 C2 106.51(13)
C7 C3 C2 98.85(12)
C4 C3 H3 116.2
C7 C3 H3 116.2
C2 C3 H3 116.2
C5 C4 C3 107.89(14)
C5 C4 H4 126.1
C3 C4 H4 126.1
C4 C5 C6 107.82(16)
C4 C5 H5 126.1
C6 C5 H5 126.1
C5 C6 C7 100.42(13)
C5 C6 C1 107.62(13)
C7 C6 C1 97.96(13)
C5 C6 H6 116.1
C7 C6 H6 116.1
C1 C6 H6 116.1
C6 C7 C3 94.05(13)
C6 C7 H7A 112.9
C3 C7 H7A 112.9
C6 C7 H7B 112.9
C3 C7 H7B 112.9
H7A C7 H7B 110.3
O2 C8 O1 119.75(16)
O2 C8 C1 130.15(16)
O1 C8 C1 110.09(14)
O3 C9 O1 119.88(16)
O3 C9 C2 130.14(16)
O1 C9 C2 109.96(13)
C8 O1 C9 110.63(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C8 . 1.502(2) ?
C1 C2 . 1.535(2) ?
C1 C6 . 1.578(2) ?
C1 H1 . 1.0000 ?
C2 C9 . 1.503(2) ?
C2 C3 . 1.575(2) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.518(3) ?
C3 C7 . 1.547(2) ?
C3 H3 . 1.0000 ?
C4 C5 . 1.332(3) ?
C4 H4 . .9500 ?
C5 C6 . 1.518(2) ?
C5 H5 . .9500 ?
C6 C7 . 1.545(2) ?
C6 H6 . 1.0000 ?
C7 H7A . .9900 ?
C7 H7B . .9900 ?
C8 O2 . 1.198(2) ?
C8 O1 . 1.389(2) ?
C9 O3 . 1.193(2) ?
C9 O1 . 1.400(2) ?
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 C9 -2.86(15)
C6 C1 C2 C9 117.18(13)
C8 C1 C2 C3 -122.25(13)
C6 C1 C2 C3 -2.21(15)
C9 C2 C3 C4 -44.70(18)
C1 C2 C3 C4 68.03(15)
C9 C2 C3 C7 -148.22(14)
C1 C2 C3 C7 -35.49(15)
C7 C3 C4 C5 33.14(17)
C2 C3 C4 C5 -69.37(16)
C3 C4 C5 C6 -.39(18)
C4 C5 C6 C7 -32.57(17)
C4 C5 C6 C1 69.33(18)
C8 C1 C6 C5 48.63(18)
C2 C1 C6 C5 -64.50(17)
C8 C1 C6 C7 152.28(13)
C2 C1 C6 C7 39.15(14)
C5 C6 C7 C3 49.16(15)
C1 C6 C7 C3 -60.50(13)
C4 C3 C7 C6 -49.33(14)
C2 C3 C7 C6 59.35(14)
C2 C1 C8 O2 -176.41(17)
C6 C1 C8 O2 71.3(2)
C2 C1 C8 O1 3.91(16)
C6 C1 C8 O1 -108.37(15)
C1 C2 C9 O3 -177.39(17)
C3 C2 C9 O3 -65.3(2)
C1 C2 C9 O1 1.01(16)
C3 C2 C9 O1 113.10(14)
O2 C8 O1 C9 176.83(14)
C1 C8 O1 C9 -3.45(17)
O3 C9 O1 C8 -179.94(15)
C2 C9 O1 C8 1.47(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2005957
