#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/54/1505446.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_1505446
loop_
_publ_author_name
'Mei, Xuefeng'
'Liu, Shuanglong'
'Wolf, Christian'
_publ_section_title
;
 Template-controlled face-to-face stacking of olefinic and aromatic
 carboxylic acids in the solid state.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2729
_journal_page_last               2732
_journal_paper_doi               10.1021/ol071039c
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C8 H12 O10'
_chemical_formula_sum            'C8 H12 O10'
_chemical_formula_weight         268.18
_chemical_name_common            CBTA
_chemical_name_systematic
;
 1,2,3,4-cyclobutane tetracarboxylic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.928(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.081(2)
_cell_length_b                   15.034(5)
_cell_length_c                   12.304(4)
_cell_measurement_temperature    187(2)
_cell_volume                     1096.3(6)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'XSEED, L. Barbour (1999); http:\x-seed.net'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      187(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'SMART platform CCD, Siemens/Bruker'
_diffrn_measurement_method       '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  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9293
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.9954
_exptl_absorpt_correction_T_min  0.9847
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2568
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0432
_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)+(0.0760P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1228
_reflns_number_gt                1891
_reflns_number_total             2568
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol071039csi20070508_032348.cif
_cod_data_source_block           d:\shuang~1\crysta~1\04136\work\04136
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1096.4(6)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1505446
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 1.1268(2) 0.15021(9) 0.53234(11) 0.0246(3) Uani 1 1 d
O2 O 1.4478(2) 0.20148(9) 0.49480(11) 0.0215(3) Uani 1 1 d
O3 O 1.1028(2) 0.12412(8) 0.27537(10) 0.0208(3) Uani 1 1 d
O4 O 1.3556(2) 0.19569(9) 0.20011(11) 0.0236(3) Uani 1 1 d
O5 O 0.6785(2) 0.41616(8) 0.13845(10) 0.0240(3) Uani 1 1 d
O6 O 0.9391(2) 0.45472(9) 0.28880(10) 0.0208(3) Uani 1 1 d
O7 O 0.5720(2) 0.38941(8) 0.39653(11) 0.0221(3) Uani 1 1 d
O8 O 0.8353(2) 0.35690(10) 0.54968(11) 0.0257(3) Uani 1 1 d
O9 O 1.2394(3) -0.03646(13) 0.61430(14) 0.0449(5) Uani 1 1 d
O10 O 1.5860(2) 0.05540(9) 0.16858(12) 0.0233(3) Uani 1 1 d
C1 C 1.1193(3) 0.28109(12) 0.41836(14) 0.0155(4) Uani 1 1 d
C2 C 1.1298(3) 0.28165(11) 0.29239(14) 0.0151(4) Uani 1 1 d
C3 C 0.8698(3) 0.30144(11) 0.26086(14) 0.0157(4) Uani 1 1 d
C4 C 0.8609(3) 0.28368(11) 0.38479(14) 0.0155(4) Uani 1 1 d
C5 C 1.2285(3) 0.20372(11) 0.48825(14) 0.0168(4) Uani 1 1 d
C6 C 1.1922(3) 0.19249(11) 0.25399(14) 0.0161(4) Uani 1 1 d
C7 C 0.8167(3) 0.39555(11) 0.22191(14) 0.0160(4) Uani 1 1 d
C8 C 0.7396(3) 0.34922(11) 0.44256(14) 0.0173(4) Uani 1 1 d
H1 H 1.189(3) 0.3333(13) 0.4530(16) 0.011(4) Uiso 1 1 d
H2 H 1.223(3) 0.3279(13) 0.2708(15) 0.014(5) Uiso 1 1 d
H3 H 0.779(3) 0.2608(13) 0.2067(16) 0.018(5) Uiso 1 1 d
H4 H 0.788(3) 0.2275(13) 0.3902(17) 0.018(5) Uiso 1 1 d
H5 H 1.508(5) 0.1610(18) 0.541(2) 0.048(8) Uiso 1 1 d
H6 H 1.401(5) 0.1401(19) 0.196(2) 0.058(9) Uiso 1 1 d
H7 H 0.911(4) 0.5063(17) 0.265(2) 0.031(6) Uiso 1 1 d
H8 H 0.758(5) 0.3946(18) 0.576(2) 0.048(8) Uiso 1 1 d
H9 H 1.233(7) 0.020(3) 0.583(4) 0.104(13) Uiso 1 1 d
H10 H 1.134(6) -0.070(2) 0.582(3) 0.069(10) Uiso 1 1 d
H11 H 1.657(5) 0.044(2) 0.242(3) 0.065(9) Uiso 1 1 d
H12 H 1.537(4) -0.002(2) 0.139(2) 0.055(8) 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
C5 O2 H5 109.6(18)
C6 O4 H6 106(2)
C7 O6 H7 111.2(16)
C8 O8 H8 106.4(19)
H9 O9 H10 113(3)
H11 O10 H12 104(2)
C5 C1 C4 117.85(14)
C5 C1 C2 117.25(14)
C4 C1 C2 89.98(12)
C5 C1 H1 106.6(11)
C4 C1 H1 115.5(11)
C2 C1 H1 109.1(11)
C6 C2 C1 112.13(14)
C6 C2 C3 113.82(14)
C1 C2 C3 89.07(12)
C6 C2 H2 110.5(12)
C1 C2 H2 115.5(11)
C3 C2 H2 114.5(11)
C7 C3 C4 114.83(14)
C7 C3 C2 112.90(14)
C4 C3 C2 88.82(12)
C7 C3 H3 108.8(11)
C4 C3 H3 114.9(12)
C2 C3 H3 115.8(11)
C8 C4 C1 118.13(14)
C8 C4 C3 118.58(14)
C1 C4 C3 90.57(13)
C8 C4 H4 105.1(12)
C1 C4 H4 114.7(11)
C3 C4 H4 109.6(12)
O1 C5 O2 124.42(16)
O1 C5 C1 124.17(15)
O2 C5 C1 111.40(14)
O3 C6 O4 124.37(16)
O3 C6 C2 121.98(16)
O4 C6 C2 113.59(15)
O5 C7 O6 122.82(16)
O5 C7 C3 124.63(16)
O6 C7 C3 112.55(14)
O7 C8 O8 124.04(17)
O7 C8 C4 123.86(16)
O8 C8 C4 112.09(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.214(2)
O2 C5 1.318(2)
O2 H5 0.86(3)
O3 C6 1.219(2)
O4 C6 1.313(2)
O4 H6 0.89(3)
O5 C7 1.213(2)
O6 C7 1.322(2)
O6 H7 0.83(3)
O7 C8 1.211(2)
O8 C8 1.321(2)
O8 H8 0.84(3)
O9 H9 0.93(5)
O9 H10 0.84(4)
O10 H11 0.93(3)
O10 H12 0.95(3)
C1 C5 1.509(2)
C1 C4 1.533(2)
C1 C2 1.565(2)
C1 H1 0.95(2)
C2 C6 1.498(2)
C2 C3 1.570(2)
C2 H2 0.97(2)
C3 C7 1.506(2)
C3 C4 1.561(2)
C3 H3 0.98(2)
C4 C8 1.502(2)
C4 H4 0.96(2)
