#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/51/1505109.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_1505109
loop_
_publ_author_name
'Nath, K.G.'
'Ivasenko, O.'
'MacLeod, J.M.'
'Miwa, J.A.'
'Wuest, J.D.'
'Nanci, A.'
'Perepichka, D.F.'
'Rosei, F.'
_publ_section_title
;
 Crystal Engineering in Two Dimensions: An Approach to Molecular
 Nanopatterning
;
_journal_issue                   45
_journal_name_full               'Journal of Physical Chemistry C'
_journal_page_first              16996
_journal_paper_doi               10.1021/jp0762774
_journal_volume                  111
_journal_year                    2007
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C6 H14 O, C9 H6 O6'
_chemical_formula_sum            'C15 H20 O7'
_chemical_formula_weight         312.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.199(3)
_cell_angle_beta                 93.133(2)
_cell_angle_gamma                110.892(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2763(4)
_cell_length_b                   8.6205(4)
_cell_length_c                   11.9930(5)
_cell_measurement_reflns_used    5525
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      71.92
_cell_measurement_theta_min      3.85
_cell_volume                     765.37(6)
_computing_cell_refinement       'SMART (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      220(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Montel 200 optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.071
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            19516
_diffrn_reflns_theta_full        72.58
_diffrn_reflns_theta_max         72.58
_diffrn_reflns_theta_min         3.85
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_T_max  0.9558
_exptl_absorpt_correction_T_min  0.7590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0066(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2913
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0955P)²+0.1058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1470
_refine_ls_wR_factor_ref         0.1565
_reflns_number_gt                2280
_reflns_number_total             2913
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jp0762774si20070805_103315.cif
_cod_data_source_block           perep3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (21
time).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (26
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (28 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1505109
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O71 O -0.03740(18) 0.71626(17) 0.46701(12) 0.0385(4) Uani 1 1 d .
O72 O 0.18520(17) 0.86385(16) 0.61354(11) 0.0346(4) Uani 1 1 d D
H72 H 0.112(4) 0.780(4) 0.651(3) 0.096(11) Uiso 1 1 d D
O81 O 0.68167(17) 1.37858(16) 0.57526(11) 0.0352(4) Uani 1 1 d .
O82 O 0.65927(18) 1.45627(17) 0.41185(12) 0.0383(4) Uani 1 1 d D
H82 H 0.778(3) 1.550(4) 0.447(3) 0.071(9) Uiso 1 1 d D
O91 O 0.18166(18) 1.12975(19) 0.09535(12) 0.0405(4) Uani 1 1 d .
O92 O -0.04471(19) 0.90582(19) 0.11537(13) 0.0439(4) Uani 1 1 d D
H92 H -0.098(5) 0.890(5) 0.031(3) 0.118(14) Uiso 1 1 d D
C1 C 0.1928(2) 0.9597(2) 0.44452(15) 0.0242(4) Uani 1 1 d .
C2 C 0.3535(2) 1.0962(2) 0.49234(15) 0.0250(4) Uani 1 1 d .
H2 H 0.4084 1.1109 0.5670 0.030 Uiso 1 1 calc R
C3 C 0.4318(2) 1.2104(2) 0.42854(15) 0.0246(4) Uani 1 1 d .
C4 C 0.3509(2) 1.1891(2) 0.31824(16) 0.0273(4) Uani 1 1 d .
H4 H 0.4042 1.2664 0.2755 0.033 Uiso 1 1 calc R
C5 C 0.1902(2) 1.0526(2) 0.27097(15) 0.0258(4) Uani 1 1 d .
C6 C 0.1118(2) 0.9385(2) 0.33444(16) 0.0264(4) Uani 1 1 d .
H6 H 0.0036 0.8466 0.3026 0.032 Uiso 1 1 calc R
C7 C 0.1027(2) 0.8344(2) 0.50907(16) 0.0264(4) Uani 1 1 d .
C8 C 0.6034(2) 1.3558(2) 0.48057(15) 0.0267(4) Uani 1 1 d .
C9 C 0.1063(2) 1.0308(2) 0.15305(16) 0.0292(4) Uani 1 1 d .
O10 O -0.00763(19) 0.64106(18) 0.70880(12) 0.0417(4) Uani 1 1 d D
H10 H -0.113(4) 0.549(4) 0.660(3) 0.076(9) Uiso 1 1 d D
C11 C 0.0321(3) 0.5876(2) 0.80722(18) 0.0381(5) Uani 1 1 d .
H11A H 0.0376 0.4729 0.7807 0.046 Uiso 1 1 calc R
H11B H -0.0607 0.5795 0.8556 0.046 Uiso 1 1 calc R
C12 C 0.2047(3) 0.7158(3) 0.87795(17) 0.0360(5) Uani 1 1 d .
H12A H 0.2027 0.8323 0.8964 0.043 Uiso 1 1 calc R
H12B H 0.2982 0.7148 0.8314 0.043 Uiso 1 1 calc R
C13 C 0.2452(3) 0.6760(3) 0.99095(17) 0.0358(5) Uani 1 1 d .
H13A H 0.1517 0.6773 1.0375 0.043 Uiso 1 1 calc R
H13B H 0.2467 0.5594 0.9724 0.043 Uiso 1 1 calc R
C14 C 0.4201(3) 0.8050(3) 1.06292(18) 0.0419(5) Uani 1 1 d .
H14A H 0.4197 0.9219 1.0781 0.050 Uiso 1 1 calc R
H14B H 0.5134 0.8004 1.0168 0.050 Uiso 1 1 calc R
C15 C 0.4631(3) 0.7742(3) 1.17924(19) 0.0459(6) Uani 1 1 d .
H15A H 0.5624 0.8763 1.2266 0.055 Uiso 1 1 calc R
H15B H 0.3625 0.7624 1.2207 0.055 Uiso 1 1 calc R
C16 C 0.5072(4) 0.6169(4) 1.1689(2) 0.0586(7) Uani 1 1 d .
H16A H 0.4071 0.5141 1.1263 0.088 Uiso 1 1 calc R
H16B H 0.5365 0.6087 1.2461 0.088 Uiso 1 1 calc R
H16C H 0.6064 0.6267 1.1277 0.088 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
C7 O72 H72 108(2) ?
C8 O82 H82 110.9(18) ?
C9 O92 H92 115(2) ?
C6 C1 C2 120.14(15) y
C6 C1 C7 118.04(15) y
C2 C1 C7 121.82(16) y
C3 C2 C1 119.53(16) y
C3 C2 H2 120.2 ?
C1 C2 H2 120.2 ?
C4 C3 C2 120.39(15) y
C4 C3 C8 120.55(15) y
C2 C3 C8 119.06(16) y
C3 C4 C5 119.82(16) y
C3 C4 H4 120.1 ?
C5 C4 H4 120.1 ?
C6 C5 C4 119.90(16) y
C6 C5 C9 120.88(15) y
C4 C5 C9 119.21(15) y
C1 C6 C5 120.22(15) y
C1 C6 H6 119.9 ?
C5 C6 H6 119.9 ?
O71 C7 O72 123.73(16) y
O71 C7 C1 121.43(16) y
O72 C7 C1 114.83(14) y
O81 C8 O82 124.18(15) y
O81 C8 C3 123.44(15) y
O82 C8 C3 112.38(15) y
O91 C9 O92 123.43(17) y
O91 C9 C5 120.10(15) y
O92 C9 C5 116.49(15) y
C11 O10 H10 108(2) ?
O10 C11 C12 109.98(15) y
O10 C11 H11A 109.7 ?
C12 C11 H11A 109.7 ?
O10 C11 H11B 109.7 ?
C12 C11 H11B 109.7 ?
H11A C11 H11B 108.2 ?
C11 C12 C13 112.39(15) y
C11 C12 H12A 109.1 ?
C13 C12 H12A 109.1 ?
C11 C12 H12B 109.1 ?
C13 C12 H12B 109.1 ?
H12A C12 H12B 107.9 ?
C14 C13 C12 112.70(16) y
C14 C13 H13A 109.1 ?
C12 C13 H13A 109.1 ?
C14 C13 H13B 109.1 ?
C12 C13 H13B 109.1 ?
H13A C13 H13B 107.8 ?
C13 C14 C15 114.54(17) y
C13 C14 H14A 108.6 ?
C15 C14 H14A 108.6 ?
C13 C14 H14B 108.6 ?
C15 C14 H14B 108.6 ?
H14A C14 H14B 107.6 ?
C16 C15 C14 114.5(2) y
C16 C15 H15A 108.6 ?
C14 C15 H15A 108.6 ?
C16 C15 H15B 108.6 ?
C14 C15 H15B 108.6 ?
H15A C15 H15B 107.6 ?
C15 C16 H16A 109.5 ?
C15 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C15 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O71 C7 1.215(2) y
O72 C7 1.314(2) y
O72 H72 0.98(3) ?
O81 C8 1.211(2) y
O82 C8 1.323(2) y
O82 H82 1.01(3) ?
O91 C9 1.246(2) y
O92 C9 1.291(2) y
O92 H92 1.04(3) ?
C1 C6 1.387(2) y
C1 C2 1.397(2) y
C1 C7 1.491(2) y
C2 C3 1.394(2) y
C2 H2 0.94 ?
C3 C4 1.389(2) y
C3 C8 1.493(2) y
C4 C5 1.396(2) y
C4 H4 0.94 ?
C5 C6 1.391(2) y
C5 C9 1.479(2) y
C6 H6 0.94 ?
O10 C11 1.430(2) y
O10 H10 0.98(3) ?
C11 C12 1.505(3) y
C11 H11a 0.98 ?
C11 H11b 0.98 ?
C12 C13 1.525(2) y
C12 H12a 0.98 ?
C12 H12b 0.98 ?
C13 C14 1.524(3) y
C13 H13a 0.98 ?
C13 H13b 0.98 ?
C14 C15 1.529(3) y
C14 H14a 0.98 ?
C14 H14b 0.98 ?
C15 C16 1.504(3) y
C15 H15a 0.98 ?
C15 H15b 0.98 ?
C16 H16a 0.97 ?
C16 H16b 0.97 ?
C16 H16c 0.97 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O72 H72 O10 0.98(3) 1.59(3) 2.5749(17) 179(3) .
O82 H82 O71 1.01(3) 1.63(3) 2.6156(17) 162(3) 1_665
O92 H92 O91 1.04(3) 1.57(3) 2.6123(19) 178(3) 2_575
O10 H10 O81 0.98(3) 1.83(3) 2.8141(19) 177(3) 1_445
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
C6 C1 C2 C3 -0.1(3) y
C7 C1 C2 C3 -179.66(16) y
C1 C2 C3 C4 0.0(3) y
C1 C2 C3 C8 179.95(15) y
C2 C3 C4 C5 0.0(3) y
C8 C3 C4 C5 -179.85(16) y
C3 C4 C5 C6 -0.1(3) y
C3 C4 C5 C9 -179.52(17) y
C2 C1 C6 C5 0.1(3) y
C7 C1 C6 C5 179.67(17) y
C4 C5 C6 C1 0.0(3) y
C9 C5 C6 C1 179.43(17) y
C6 C1 C7 O71 0.2(3) y
C2 C1 C7 O71 179.77(17) y
C6 C1 C7 O72 -178.88(16) y
C2 C1 C7 O72 0.6(3) y
C4 C3 C8 O81 -178.41(18) y
C2 C3 C8 O81 1.7(3) y
C4 C3 C8 O82 1.8(3) y
C2 C3 C8 O82 -178.13(16) y
C6 C5 C9 O91 -176.98(18) y
C4 C5 C9 O91 2.5(3) y
C6 C5 C9 O92 2.7(3) y
C4 C5 C9 O92 -177.85(17) y
O10 C11 C12 C13 173.99(18) y
C11 C12 C13 C14 179.83(19) y
C12 C13 C14 C15 177.8(2) y
C13 C14 C15 C16 71.1(3) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30651557
