#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/11/2011164.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_2011164
loop_
_publ_author_name
'Niwayama, Satomi'
'Holt, Elizabeth M.'
_publ_section_title
;
 6-Dimethoxymethyl-1-methoxycarbonylbicyclo[3.1.0]hex-2-ene-2-carboxylic
 acid
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              e300
_journal_page_last               e301
_journal_paper_doi               10.1107/S0108270100007757
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C12 H16 O6'
_chemical_formula_sum            'C12 H16 O6'
_chemical_formula_weight         256.25
_chemical_name_systematic
;
6-Dimethoxymethyl-1-methoxycarbonylbicyclo[3.1.0]hex-2-ene-2-carboxylic 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'
_cell_angle_alpha                90.00
_cell_angle_beta                 94.57(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.537(4)
_cell_length_b                   13.602(8)
_cell_length_c                   12.779(5)
_cell_measurement_reflns_used    28
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.8
_cell_measurement_theta_min      5.6
_cell_volume                     1305.9(12)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1991)'
_computing_data_reduction        XSCANS
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .944
_diffrn_measured_fraction_theta_max .944
_diffrn_measurement_device_type  'Syntex P4 four-circle'
_diffrn_measurement_method       θ/2θ
_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  .126
_diffrn_reflns_av_sigmaI/netI    .0904
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3773
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         4.27
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             544
_exptl_crystal_size_max          .2
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_refine_diff_density_max         .11
_refine_diff_density_min         -.08
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .992
_refine_ls_R_factor_all          .095
_refine_ls_R_factor_gt           .067
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1511P)²+0.1243P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .233
_reflns_number_gt                1975
_reflns_number_total             2845
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qa0312.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.1511P)^2^+0.1243P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.1511P)^2^+0.1243P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2011164
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_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 .7023(3) .72696(17) .15677(19) .0400(6) Uani d . 1 . . C
C2 .6771(3) .66163(18) .06139(18) .0394(6) Uani d . 1 . . C
C3 .5121(3) .6704(2) .0124(2) .0485(6) Uani d . 1 . . C
H3A .4460 .6347 -.0535 .050 Uiso d R 1 . . H
C4 .4010(3) .7463(2) .0634(2) .0543(7) Uani d . 1 . . C
H4A .2921 .7181 .0837 .080 Uiso d R 1 . . H
H4B .3733 .8005 .0169 .080 Uiso d R 1 . . H
C5 .5208(3) .77995(18) .1608(2) .0483(7) Uani d . 1 . . C
H5A .5221 .8484 .1790 .080 Uiso d R 1 . . H
C6 .5815(3) .70636(17) .24505(19) .0421(6) Uani d . 1 . . C
H6A .6222 .7353 .3112 .080 Uiso d R 1 . . H
C7 .8776(3) .78091(17) .1753(2) .0472(6) Uani d . 1 . . C
C8 1.0960(4) .8403(3) .3052(3) .0757(10) Uani d . 1 . . C
H8A 1.1178 .8439 .3802 .080 Uiso d R 1 . . H
H8B 1.1906 .8045 .2765 .080 Uiso d R 1 . . H
H8C 1.0905 .9056 .2765 .080 Uiso d R 1 . . H
C9 .8167(3) .59090(18) .03472(18) .0406(6) Uani d . 1 . . C
C10 .4876(3) .60834(18) .25657(18) .0413(6) Uani d . 1 . . C
H10A .4265 .5917 .1901 .080 Uiso d R 1 . . H
C11 .7129(5) .5464(3) .3835(3) .0862(12) Uani d . 1 . . C
H11A .7866 .4900 .3998 .080 Uiso d R 1 . . H
H11B .7868 .6029 .3750 .080 Uiso d R 1 . . H
H11C .6381 .5580 .4396 .080 Uiso d R 1 . . H
C12 .2272(4) .5514(3) .3339(3) .0688(9) Uani d . 1 . . C
H12A .1464 .5683 .3854 .080 Uiso d R 1 . . H
H12B .1629 .5462 .2662 .080 Uiso d R 1 . . H
H12C .2831 .4897 .3521 .080 Uiso d R 1 . . H
O1 .9631(3) .81238(18) .10620(19) .0708(7) Uani d . 1 . . O
O2 .9284(3) .79096(16) .27818(17) .0628(6) Uani d . 1 . . O
O3 .9586(2) .58392(15) .08861(15) .0550(6) Uani d . 1 . . O
O4 .7758(2) .53716(16) -.05012(15) .0590(6) Uani d . 1 . . O
H4C .8645 .4866 -.0518 .050 Uiso d R 1 . . H
O5 .6047(3) .52982(14) .28781(16) .0576(6) Uani d . 1 . . O
O6 .3600(2) .62621(14) .32987(15) .0529(5) 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 .0363(12) .0356(11) .0497(13) .0031(9) .0133(10) -.0003(9)
C2 .0377(12) .0417(12) .0402(12) .0013(10) .0123(9) .0031(9)
C3 .0431(13) .0599(15) .0435(13) .0041(12) .0087(10) .0068(11)
C4 .0413(13) .0602(16) .0626(16) .0137(12) .0127(11) .0164(13)
C5 .0400(13) .0375(12) .0700(17) .0049(10) .0206(11) -.0011(11)
C6 .0432(13) .0387(12) .0460(13) -.0001(10) .0138(10) -.0081(10)
C7 .0409(13) .0350(12) .0673(17) .0024(10) .0147(11) -.0059(11)
C8 .0465(16) .079(2) .101(3) -.0055(16) -.0009(16) -.031(2)
C9 .0398(12) .0439(12) .0392(11) .0002(10) .0104(9) -.0045(9)
C10 .0435(12) .0428(13) .0389(12) -.0020(10) .0113(9) -.0023(9)
C11 .062(2) .096(3) .098(3) .014(2) -.0106(19) .025(2)
C12 .0543(16) .082(2) .071(2) -.0231(16) .0148(14) .0068(17)
O1 .0568(13) .0771(15) .0816(15) -.0193(11) .0250(11) .0044(12)
O2 .0467(11) .0706(14) .0714(13) -.0107(10) .0059(9) -.0171(11)
O3 .0470(10) .0614(12) .0559(11) .0141(9) .0000(8) -.0175(9)
O4 .0450(10) .0710(13) .0606(12) .0110(9) .0023(8) -.0241(10)
O5 .0607(12) .0435(10) .0706(13) .0059(9) .0170(9) .0057(9)
O6 .0454(10) .0592(11) .0564(11) -.0067(8) .0194(8) -.0044(9)
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
_geom_angle_publ_flag
C2 C1 C7 117.63(19) no
C2 C1 C6 116.36(19) no
C7 C1 C6 122.5(2) no
C2 C1 C5 104.3(2) no
C7 C1 C5 122.1(2) no
C6 C1 C5 58.83(16) no
C3 C2 C9 126.4(2) no
C3 C2 C1 112.0(2) no
C9 C2 C1 121.4(2) no
C2 C3 C4 112.4(2) no
C2 C3 H3A 133.1 no
C4 C3 H3A 114.5 no
C3 C4 C5 104.0(2) no
C3 C4 H4A 111.1 no
C5 C4 H4A 110.9 no
C3 C4 H4B 111.1 no
C5 C4 H4B 110.8 no
H4A C4 H4B 108.9 no
C6 C5 C1 59.93(15) no
C6 C5 C4 120.0(2) no
C1 C5 C4 107.1(2) no
C6 C5 H5A 118.2 no
C1 C5 H5A 117.8 no
C4 C5 H5A 118.4 no
C5 C6 C10 122.1(2) no
C5 C6 C1 61.24(15) no
C10 C6 C1 122.68(19) no
C5 C6 H6A 114.3 no
C10 C6 H6A 113.1 no
C1 C6 H6A 114.0 no
O1 C7 O2 123.3(2) no
O1 C7 C1 124.5(3) no
O2 C7 C1 112.2(2) no
O2 C8 H8A 109.8 no
O2 C8 H8B 109.5 no
H8A C8 H8B 109.5 no
O2 C8 H8C 109.1 no
H8A C8 H8C 109.5 no
H8B C8 H8C 109.5 no
O3 C9 O4 123.5(2) no
O3 C9 C2 121.5(2) no
O4 C9 C2 115.0(2) no
O6 C10 O5 112.48(19) no
O6 C10 C6 105.02(19) no
O5 C10 C6 113.7(2) no
O6 C10 H10A 108.8 no
O5 C10 H10A 108.3 no
C6 C10 H10A 108.3 no
O5 C11 H11A 109.8 no
O5 C11 H11B 109.0 no
H11A C11 H11B 109.5 no
O5 C11 H11C 109.6 no
H11A C11 H11C 109.5 no
H11B C11 H11C 109.5 no
O6 C12 H12A 109.8 no
O6 C12 H12B 109.0 no
H12A C12 H12B 109.5 no
O6 C12 H12C 109.7 no
H12A C12 H12C 109.5 no
H12B C12 H12C 109.5 no
C7 O2 C8 117.1(3) no
C9 O4 H4C 107.2 no
C10 O5 C11 114.8(2) no
C10 O6 C12 114.5(2) no
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 C2 . 1.508(3) yes
C1 C7 . 1.513(4) yes
C1 C6 . 1.531(3) yes
C1 C5 . 1.551(3) yes
C2 C3 . 1.353(4) yes
C2 C9 . 1.485(3) yes
C3 C4 . 1.509(4) yes
C3 H3A . 1.0613 no
C4 C5 . 1.548(4) yes
C4 H4A . .9600 no
C4 H4B . .9599 no
C5 C6 . 1.514(4) yes
C5 H5A . .9601 no
C6 C10 . 1.522(3) yes
C6 H6A . .9600 no
C7 O1 . 1.212(3) yes
C7 O2 . 1.347(3) yes
C8 O2 . 1.448(4) yes
C8 H8A . .9601 no
C8 H8B . .9600 no
C8 H8C . .9601 no
C9 O3 . 1.228(3) yes
C9 O4 . 1.323(3) yes
C10 O6 . 1.416(3) yes
C10 O5 . 1.422(3) yes
C10 H10A . .9600 no
C11 O5 . 1.433(4) yes
C11 H11A . .9600 no
C11 H11B . .9600 no
C11 H11C . .9600 no
C12 O6 . 1.431(3) yes
C12 H12A . .9600 no
C12 H12B . .9600 no
C12 H12C . .9600 no
O4 H4C . .9600 yes
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
O4 H4c O3 3_765 .96 1.74 2.668(3) 162
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_publ_flag
C3 C2 C9 O4 5.0(4) no
C2 C1 C7 O1 34.3(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 355729
