#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/78/1517851.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_1517851
loop_
_publ_author_name
'Velasco, V.'
'Aguilà, D.'
'Barrios, L. A.'
'Borilovic, I.'
'Roubeau, O.'
'Ribas-Ariño, J.'
'Fumanal, M.'
'Teat, S. J.'
'Aromí, G.'
_publ_section_title
;
 New coordination features; a bridging pyridine and the forced shortest
 non-covalent distance between two CO32−species
;
_journal_issue                   1
_journal_name_full               'Chem. Sci.'
_journal_page_first              123
_journal_paper_doi               10.1039/C4SC02491E
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C23 H17 N O6'
_chemical_formula_sum            'C23 H17 N O6'
_chemical_formula_weight         403.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.073(6)
_cell_length_b                   7.448(2)
_cell_length_c                   23.393(6)
_cell_measurement_reflns_used    1266
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.76
_cell_measurement_theta_min      2.83
_cell_volume                     3671.6(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX II CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         'Advanced Light Source station 11.3.1'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.77490
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_av_sigmaI/netI    0.0514
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12670
_diffrn_reflns_theta_full        24.05
_diffrn_reflns_theta_max         24.10
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS Bruker AXS Madison WI US'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         2239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0454
_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)+(0.0675P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1156
_reflns_number_gt                1551
_reflns_number_total             2239
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4sc02491e2.cif
_cod_data_source_block           ibxx13
_cod_depositor_comments
'Adding full bibliography for 1517851--1517853.cif.'
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1517851
#BEGIN Tags that were not found in dictionaries:
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
O1 O 0.43259(10) 0.8152(3) 0.46324(10) 0.0306(6) Uani 1 1 d .
O2 O 0.38904(9) 0.7535(3) 0.56473(9) 0.0273(6) Uani 1 1 d .
H2 H 0.4079(17) 0.812(4) 0.4974(15) 0.041 Uiso 1 1 d .
O3 O 0.34105(10) 0.6600(3) 0.66171(11) 0.0351(6) Uani 1 1 d .
H3 H 0.3435(17) 0.691(5) 0.6227(16) 0.053 Uiso 1 1 d .
O4 O 0.75890(10) 0.6563(3) 0.43087(9) 0.0288(6) Uani 1 1 d .
H4 H 0.7904(17) 0.615(5) 0.4561(15) 0.043 Uiso 1 1 d .
O5 O 0.81294(9) 0.5098(3) 0.51820(9) 0.0267(6) Uani 1 1 d .
O6 O 0.86888(9) 0.3721(3) 0.60691(11) 0.0314(6) Uani 1 1 d .
H6 H 0.8644(17) 0.421(5) 0.5697(16) 0.047 Uiso 1 1 d .
N1 N 0.59596(11) 0.7011(3) 0.46618(11) 0.0219(7) Uani 1 1 d .
C1 C 0.54240(14) 0.7742(4) 0.44567(13) 0.0227(8) Uani 1 1 d .
C2 C 0.53833(14) 0.8512(4) 0.39191(14) 0.0254(8) Uani 1 1 d .
H2A H 0.4993 0.8985 0.3782 0.030 Uiso 1 1 calc R
C3 C 0.59266(15) 0.8574(4) 0.35855(15) 0.0272(8) Uani 1 1 d .
H3A H 0.5916 0.9108 0.3217 0.033 Uiso 1 1 calc R
C4 C 0.64862(14) 0.7846(4) 0.37970(14) 0.0261(8) Uani 1 1 d .
H4A H 0.6864 0.7876 0.3576 0.031 Uiso 1 1 calc R
C5 C 0.64835(14) 0.7082(4) 0.43319(13) 0.0217(8) Uani 1 1 d .
C6 C 0.48856(14) 0.7661(4) 0.48628(14) 0.0224(8) Uani 1 1 d .
C7 C 0.49552(14) 0.7148(4) 0.54076(13) 0.0237(8) Uani 1 1 d .
H7A H 0.5369 0.6854 0.5538 0.028 Uiso 1 1 calc R
C8 C 0.44370(15) 0.7019(4) 0.58054(14) 0.0253(8) Uani 1 1 d .
C9 C 0.45237(14) 0.6287(4) 0.63793(13) 0.0229(8) Uani 1 1 d .
C10 C 0.40077(15) 0.6084(4) 0.67575(15) 0.0291(9) Uani 1 1 d .
C11 C 0.40881(16) 0.5291(4) 0.72860(15) 0.0315(9) Uani 1 1 d .
H11A H 0.3733 0.5143 0.7531 0.038 Uiso 1 1 calc R
C12 C 0.46798(16) 0.4710(4) 0.74621(16) 0.0329(9) Uani 1 1 d .
H12A H 0.4730 0.4161 0.7826 0.039 Uiso 1 1 calc R
C13 C 0.51991(16) 0.4931(4) 0.71059(14) 0.0311(9) Uani 1 1 d .
H13A H 0.5608 0.4556 0.7229 0.037 Uiso 1 1 calc R
C14 C 0.51254(15) 0.5688(4) 0.65779(14) 0.0284(9) Uani 1 1 d .
H14A H 0.5486 0.5816 0.6337 0.034 Uiso 1 1 calc R
C15 C 0.70558(14) 0.6295(4) 0.46079(14) 0.0230(8) Uani 1 1 d .
C16 C 0.70323(14) 0.5456(4) 0.51149(14) 0.0228(8) Uani 1 1 d .
H16A H 0.6629 0.5260 0.5286 0.027 Uiso 1 1 calc R
C17 C 0.75876(14) 0.4842(4) 0.54099(13) 0.0229(8) Uani 1 1 d .
C18 C 0.75434(14) 0.3961(4) 0.59670(13) 0.0232(8) Uani 1 1 d .
C19 C 0.80918(14) 0.3463(4) 0.62762(14) 0.0256(8) Uani 1 1 d .
C20 C 0.80423(15) 0.2674(4) 0.68115(14) 0.0285(8) Uani 1 1 d .
H20A H 0.8416 0.2349 0.7013 0.034 Uiso 1 1 calc R
C21 C 0.74580(15) 0.2356(4) 0.70530(14) 0.0293(8) Uani 1 1 d .
H21A H 0.7428 0.1827 0.7422 0.035 Uiso 1 1 calc R
C22 C 0.69087(15) 0.2814(4) 0.67535(14) 0.0309(9) Uani 1 1 d .
H22A H 0.6504 0.2596 0.6918 0.037 Uiso 1 1 calc R
C23 C 0.69540(15) 0.3578(4) 0.62240(14) 0.0269(8) Uani 1 1 d .
H23A H 0.6576 0.3860 0.6022 0.032 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 -0.0020 0.0020
'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'
H H 0.0000 0.0000
'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'
N N -0.0031 0.0040
'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'
O O -0.0041 0.0074
'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 O1 H2 98(2)
C10 O3 H3 105(2)
C15 O4 H4 102(2)
C19 O6 H6 107(2)
C1 N1 C5 117.9(3)
N1 C1 C2 123.0(3)
N1 C1 C6 113.5(3)
C2 C1 C6 123.5(3)
C1 C2 C3 118.3(3)
C1 C2 H2A 120.9
C3 C2 H2A 120.9
C2 C3 C4 119.2(3)
C2 C3 H3A 120.4
C4 C3 H3A 120.4
C5 C4 C3 118.8(3)
C5 C4 H4A 120.6
C3 C4 H4A 120.6
N1 C5 C4 122.7(3)
N1 C5 C15 113.6(3)
C4 C5 C15 123.7(3)
C7 C6 O1 123.7(3)
C7 C6 C1 122.6(3)
O1 C6 C1 113.7(3)
C6 C7 C8 123.5(3)
C6 C7 H7A 118.2
C8 C7 H7A 118.2
O2 C8 C7 118.7(3)
O2 C8 C9 119.6(3)
C7 C8 C9 121.7(3)
C10 C9 C14 116.7(3)
C10 C9 C8 121.4(3)
C14 C9 C8 121.9(3)
O3 C10 C11 116.9(3)
O3 C10 C9 122.2(3)
C11 C10 C9 120.9(3)
C10 C11 C12 120.8(3)
C10 C11 H11A 119.6
C12 C11 H11A 119.6
C11 C12 C13 119.7(3)
C11 C12 H12A 120.1
C13 C12 H12A 120.1
C14 C13 C12 120.2(3)
C14 C13 H13A 119.9
C12 C13 H13A 119.9
C13 C14 C9 121.7(3)
C13 C14 H14A 119.1
C9 C14 H14A 119.1
O4 C15 C16 124.2(3)
O4 C15 C5 113.2(3)
C16 C15 C5 122.5(3)
C15 C16 C17 123.0(3)
C15 C16 H16A 118.5
C17 C16 H16A 118.5
O5 C17 C16 118.8(3)
O5 C17 C18 119.8(3)
C16 C17 C18 121.4(3)
C23 C18 C19 116.7(3)
C23 C18 C17 121.8(3)
C19 C18 C17 121.5(3)
O6 C19 C20 116.8(3)
O6 C19 C18 122.5(3)
C20 C19 C18 120.8(3)
C21 C20 C19 120.7(3)
C21 C20 H20A 119.6
C19 C20 H20A 119.6
C20 C21 C22 119.6(3)
C20 C21 H21A 120.2
C22 C21 H21A 120.2
C23 C22 C21 119.9(3)
C23 C22 H22A 120.0
C21 C22 H22A 120.0
C22 C23 C18 122.2(3)
C22 C23 H23A 118.9
C18 C23 H23A 118.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.348(4)
O1 H2 0.95(4)
O2 C8 1.269(4)
O3 C10 1.356(4)
O3 H3 0.94(4)
O4 C15 1.339(4)
O4 H4 0.94(4)
O5 C17 1.274(3)
O6 C19 1.362(4)
O6 H6 0.95(4)
N1 C1 1.342(4)
N1 C5 1.348(4)
C1 C2 1.385(4)
C1 C6 1.481(4)
C2 C3 1.386(4)
C2 H2A 0.9500
C3 C4 1.389(4)
C3 H3A 0.9500
C4 C5 1.375(4)
C4 H4A 0.9500
C5 C15 1.488(4)
C6 C7 1.338(4)
C7 C8 1.438(4)
C7 H7A 0.9500
C8 C9 1.461(4)
C9 C10 1.410(4)
C9 C14 1.422(4)
C10 C11 1.380(5)
C11 C12 1.383(5)
C11 H11A 0.9500
C12 C13 1.385(5)
C12 H12A 0.9500
C13 C14 1.367(4)
C13 H13A 0.9500
C14 H14A 0.9500
C15 C16 1.342(4)
C16 C17 1.433(4)
C16 H16A 0.9500
C17 C18 1.462(4)
C18 C23 1.409(4)
C18 C19 1.413(4)
C19 C20 1.387(4)
C20 C21 1.375(4)
C20 H20A 0.9500
C21 C22 1.395(4)
C21 H21A 0.9500
C22 C23 1.366(4)
C22 H22A 0.9500
C23 H23A 0.9500
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
O1 H2 O2 0.95(4) 1.68(4) 2.587(3) 157(3) .
O3 H3 O2 0.94(4) 1.73(4) 2.579(3) 149(3) .
O4 H4 O5 0.94(4) 1.72(4) 2.581(3) 151(3) .
O6 H6 O5 0.95(4) 1.75(4) 2.598(3) 147(3) .
O4 H4 O2 0.94(4) 2.35(4) 2.826(3) 111(2) 4_566
O1 H2 O5 0.95(4) 2.43(3) 2.871(3) 108(2) 4_466
