#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/63/2236316.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_2236316
loop_
_publ_author_name
'Moazeni, Amin'
'Bender, Christopher O.'
'Boeré, René T.'
_publ_section_title
;
 Dimethyl
 7-methoxytetracyclo[6.4.0.0^2,4^.0^3,7^]dodeca-1(12),5,8,10-tetraene-3,4-dicarboxylate
;
_journal_coeditor_code           HG5246
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2837
_journal_paper_doi               10.1107/S1600536812037233
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C17 H16 O5'
_chemical_formula_moiety         'C17 H16 O5'
_chemical_formula_sum            'C17 H16 O5'
_chemical_formula_weight         300.30
_chemical_name_systematic
'Dimethyl 7-methoxytetracyclo[6.4.0.0^2,4^.0^3,7^]dodeca-1(12),5,8,10-tetraene-3,4-dicarboxylate'
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 90.0280(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.892(2)
_cell_length_b                   7.9999(8)
_cell_length_c                   15.4182(15)
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.75
_cell_measurement_theta_min      2.64
_cell_volume                     2946.9(5)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2008)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 66.06
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19005
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       Block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.212
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0339
_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)+(0.0508P)²+1.4670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0941
_reflns_number_gt                2607
_reflns_number_total             3005
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            hg5246.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2236316
_cod_database_fobs_code          2236316
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
C C3 0.38022(5) 0.25083(15) 0.81435(7) 0.0222(3) Uani d . 1 1
C C6 0.42265(5) 0.09543(15) 0.64775(7) 0.0226(3) Uani d . 1 1
H H6 0.4317 -0.0146 0.6294 0.027 Uiso calc R 1 1
C C7 0.45963(5) 0.21768(15) 0.65739(7) 0.0225(2) Uani d . 1 1
H H7 0.4990 0.2036 0.6525 0.027 Uiso calc R 1 1
C C2 0.38959(5) 0.39617(14) 0.75702(7) 0.0216(2) Uani d . 1 1
H H2 0.3809 0.5104 0.7796 0.026 Uiso calc R 1 1
C C17 0.26658(5) 0.11991(17) 0.64184(9) 0.0315(3) Uani d . 1 1
H H17A 0.2585 0.0638 0.6970 0.047 Uiso calc R 1 1
H H17B 0.2406 0.0796 0.5973 0.047 Uiso calc R 1 1
H H17C 0.2620 0.2409 0.6489 0.047 Uiso calc R 1 1
C C4 0.36095(5) 0.11440(14) 0.76658(7) 0.0217(2) Uani d . 1 1
C C12 0.34945(5) -0.03788(16) 0.80631(8) 0.0285(3) Uani d . 1 1
H H12 0.3377 -0.1319 0.7733 0.034 Uiso calc R 1 1
C C16 0.27099(6) 0.67723(17) 0.60114(10) 0.0359(3) Uani d . 1 1
H H16A 0.2966 0.7588 0.5752 0.054 Uiso calc R 1 1
H H16B 0.2436 0.7356 0.6374 0.054 Uiso calc R 1 1
H H16C 0.2515 0.6162 0.5551 0.054 Uiso calc R 1 1
C C8 0.43190(5) 0.37858(15) 0.67664(7) 0.0219(3) Uani d . 1 1
C C15 0.33539(5) 0.45632(14) 0.60978(7) 0.0226(3) Uani d . 1 1
C C13 0.45429(5) 0.54272(15) 0.64747(8) 0.0264(3) Uani d . 1 1
C C11 0.35563(5) -0.04820(18) 0.89585(9) 0.0339(3) Uani d . 1 1
H H11 0.3468 -0.1496 0.9248 0.041 Uiso calc R 1 1
C C1 0.36939(5) 0.34981(14) 0.66910(7) 0.0198(2) Uani d . 1 1
C C9 0.38762(5) 0.23822(17) 0.90355(8) 0.0283(3) Uani d . 1 1
H H9 0.4012 0.3302 0.9363 0.034 Uiso calc R 1 1
C C5 0.36397(5) 0.15424(14) 0.66990(7) 0.0204(2) Uani d . 1 1
C C10 0.37463(5) 0.08795(19) 0.94345(8) 0.0339(3) Uani d . 1 1
H H10 0.3788 0.0778 1.0045 0.041 Uiso calc R 1 1
C C14 0.53073(7) 0.6835(2) 0.58505(12) 0.0471(4) Uani d . 1 1
H H14A 0.5057 0.7368 0.5429 0.071 Uiso calc R 1 1
H H14B 0.5668 0.6595 0.5575 0.071 Uiso calc R 1 1
H H14C 0.5365 0.7587 0.6344 0.071 Uiso calc R 1 1
O O5 0.32282(3) 0.08404(11) 0.61609(5) 0.0250(2) Uani d . 1 1
O O4 0.33743(4) 0.44688(12) 0.53199(6) 0.0350(2) Uani d . 1 1
O O3 0.30236(4) 0.56102(11) 0.65372(6) 0.0275(2) Uani d . 1 1
O O1 0.50578(4) 0.52885(12) 0.61514(6) 0.0344(2) Uani d . 1 1
O O2 0.42898(4) 0.67223(12) 0.65173(8) 0.0458(3) Uani d . 1 1
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 0.00 0.1350
0.00 0.00 -1.00 0.0880
1.00 1.00 1.00 0.1620
-1.00 -1.00 -1.00 0.1370
-1.00 -1.00 0.00 0.1280
1.00 1.00 -1.00 0.1460
1.00 0.00 0.00 0.1630
-1.00 1.00 -1.00 0.1160
1.00 -1.00 1.00 0.1360
1.00 -1.00 -1.00 0.1410
0.00 1.00 1.00 0.1930
0.00 -1.00 -1.00 0.1390
0.00 -1.00 0.00 0.1690
0.00 1.00 0.00 0.1210
0.00 -1.00 1.00 0.1380
0.00 1.00 -1.00 0.0570
0.00 1.00 2.00 0.1860
-1.00 2.00 2.00 0.1790
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 C3 C4 120.49(11)
C9 C3 C2 129.03(11)
C4 C3 C2 110.48(10)
C7 C6 C5 111.19(10)
C7 C6 H6 124.4
C5 C6 H6 124.4
C6 C7 C8 111.48(10)
C6 C7 H7 124.3
C8 C7 H7 124.3
C3 C2 C1 107.47(10)
C3 C2 C8 119.23(9)
C1 C2 C8 58.56(7)
C3 C2 H2 118.6
C1 C2 H2 118.6
C8 C2 H2 118.6
O5 C17 H17A 109.5
O5 C17 H17B 109.5
H17A C17 H17B 109.5
O5 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C12 C4 C3 121.20(11)
C12 C4 C5 128.50(11)
C3 C4 C5 109.67(10)
C11 C12 C4 117.92(12)
C11 C12 H12 121.0
C4 C12 H12 121.0
O3 C16 H16A 109.5
O3 C16 H16B 109.5
H16A C16 H16B 109.5
O3 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C7 C8 C13 123.16(10)
C7 C8 C1 107.10(9)
C13 C8 C1 117.74(10)
C7 C8 C2 120.91(9)
C13 C8 C2 112.49(10)
C1 C8 C2 56.75(7)
O4 C15 O3 124.71(11)
O4 C15 C1 123.62(11)
O3 C15 C1 111.66(9)
O2 C13 O1 123.86(11)
O2 C13 C8 124.31(11)
O1 C13 C8 111.83(10)
C10 C11 C12 120.81(12)
C10 C11 H11 119.6
C12 C11 H11 119.6
C2 C1 C15 126.43(10)
C2 C1 C8 64.69(8)
C15 C1 C8 119.80(9)
C2 C1 C5 105.57(9)
C15 C1 C5 121.98(10)
C8 C1 C5 103.41(9)
C10 C9 C3 118.28(12)
C10 C9 H9 120.9
C3 C9 H9 120.9
O5 C5 C6 112.94(9)
O5 C5 C4 117.42(9)
C6 C5 C4 101.49(9)
O5 C5 C1 116.86(9)
C6 C5 C1 103.35(9)
C4 C5 C1 102.69(9)
C9 C10 C11 121.25(12)
C9 C10 H10 119.4
C11 C10 H10 119.4
O1 C14 H14A 109.5
O1 C14 H14B 109.5
H14A C14 H14B 109.5
O1 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C5 O5 C17 114.42(9)
C15 O3 C16 115.20(10)
C13 O1 C14 115.38(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C3 C9 1.3902(17)
C3 C4 1.3948(17)
C3 C2 1.4776(16)
C6 C7 1.3262(17)
C6 C5 1.5179(15)
C6 H6 0.9500
C7 C8 1.4778(16)
C7 H7 0.9500
C2 C1 1.4857(16)
C2 C8 1.6060(16)
C2 H2 1.0000
C17 O5 1.4304(15)
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C4 C12 1.3910(17)
C4 C5 1.5260(15)
C12 C11 1.3908(19)
C12 H12 0.9500
C16 O3 1.4432(15)
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C8 C13 1.4874(16)
C8 C1 1.5157(16)
C15 O4 1.2028(15)
C15 O3 1.3356(14)
C15 C1 1.4906(16)
C13 O2 1.2014(16)
C13 O1 1.3323(15)
C11 C10 1.389(2)
C11 H11 0.9500
C1 C5 1.5699(16)
C9 C10 1.3856(19)
C9 H9 0.9500
C5 O5 1.4035(14)
C10 H10 0.9500
C14 O1 1.4495(16)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
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
C6 H6 O2 1_545 0.95 2.53 3.3895(16) 151
C10 H10 O5 6_556 0.95 2.54 3.2425(15) 131
C7 H7 C9 2_656 0.95 2.86 3.773(2) 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
C5 C6 C7 C8 -6.71(14)
C9 C3 C2 C1 -173.72(11)
C4 C3 C2 C1 5.71(13)
C9 C3 C2 C8 123.07(13)
C4 C3 C2 C8 -57.51(14)
C9 C3 C4 C12 -0.96(18)
C2 C3 C4 C12 179.56(10)
C9 C3 C4 C5 -172.58(10)
C2 C3 C4 C5 7.94(13)
C3 C4 C12 C11 2.51(18)
C5 C4 C12 C11 172.41(11)
C6 C7 C8 C13 -147.41(11)
C6 C7 C8 C1 -5.91(13)
C6 C7 C8 C2 55.12(14)
C3 C2 C8 C7 2.50(16)
C1 C2 C8 C7 -91.00(12)
C3 C2 C8 C13 -157.18(11)
C1 C2 C8 C13 109.32(11)
C3 C2 C8 C1 93.50(11)
C7 C8 C13 O2 169.30(13)
C1 C8 C13 O2 31.53(18)
C2 C8 C13 O2 -31.55(17)
C7 C8 C13 O1 -10.10(16)
C1 C8 C13 O1 -147.87(11)
C2 C8 C13 O1 149.05(10)
C4 C12 C11 C10 -2.25(19)
C3 C2 C1 C15 136.43(11)
C8 C2 C1 C15 -109.52(12)
C3 C2 C1 C8 -114.05(10)
C3 C2 C1 C5 -16.31(12)
C8 C2 C1 C5 97.74(9)
O4 C15 C1 C2 150.54(12)
O3 C15 C1 C2 -30.10(15)
O4 C15 C1 C8 71.47(16)
O3 C15 C1 C8 -109.17(11)
O4 C15 C1 C5 -60.80(16)
O3 C15 C1 C5 118.56(11)
C7 C8 C1 C2 116.16(10)
C13 C8 C1 C2 -99.91(11)
C7 C8 C1 C15 -124.75(11)
C13 C8 C1 C15 19.19(15)
C2 C8 C1 C15 119.09(12)
C7 C8 C1 C5 15.07(11)
C13 C8 C1 C5 159.00(10)
C2 C8 C1 C5 -101.09(9)
C4 C3 C9 C10 -0.89(17)
C2 C3 C9 C10 178.49(11)
C7 C6 C5 O5 143.12(10)
C7 C6 C5 C4 -90.27(11)
C7 C6 C5 C1 15.91(12)
C12 C4 C5 O5 42.13(16)
C3 C4 C5 O5 -147.04(10)
C12 C4 C5 C6 -81.48(14)
C3 C4 C5 C6 89.36(11)
C12 C4 C5 C1 171.82(11)
C3 C4 C5 C1 -17.34(12)
C2 C1 C5 O5 150.13(9)
C15 C1 C5 O5 -4.12(15)
C8 C1 C5 O5 -142.81(9)
C2 C1 C5 C6 -85.17(10)
C15 C1 C5 C6 120.58(11)
C8 C1 C5 C6 -18.11(11)
C2 C1 C5 C4 20.10(11)
C15 C1 C5 C4 -134.15(10)
C8 C1 C5 C4 87.16(10)
C3 C9 C10 C11 1.14(18)
C12 C11 C10 C9 0.5(2)
C6 C5 O5 C17 172.52(10)
C4 C5 O5 C17 54.92(14)
C1 C5 O5 C17 -67.78(13)
O4 C15 O3 C16 -4.97(17)
C1 C15 O3 C16 175.68(10)
O2 C13 O1 C14 0.5(2)
C8 C13 O1 C14 179.94(12)
