#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:13:32 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180417 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/86/7208692.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_7208692
loop_
_publ_author_name
'Butterhof, Christian'
'Bärwinkel, Kilian'
'Senker, Jürgen'
'Breu, Josef'
_publ_section_title
;
 Polymorphism in co-crystals: a metastable form of the ionic co-crystal 2
 HBz·1 NaBz crystallised by flash evaporation
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              6744
_journal_paper_doi               10.1039/c2ce25562f
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C21 H17 Na O6'
_chemical_formula_weight         388.34
_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                109.97(3)
_cell_angle_beta                 100.51(3)
_cell_angle_gamma                103.88(3)
_cell_formula_units_Z            2
_cell_length_a                   6.8912(14)
_cell_length_b                   12.082(2)
_cell_length_c                   13.372(3)
_cell_measurement_reflns_used    1652
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.14
_cell_measurement_theta_min      1.90
_cell_volume                     972.3(5)
_computing_cell_refinement       'STOE IPDS I'
_computing_data_collection       'STOE IPDS I'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Diamond Version 3.0e'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'STOE IPDS I'
_diffrn_measurement_method       'phi 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  0.0896
_diffrn_reflns_av_sigmaI/netI    0.1438
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8497
_diffrn_reflns_theta_full        26.14
_diffrn_reflns_theta_max         26.14
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.765
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.765
_refine_ls_R_factor_all          0.1643
_refine_ls_R_factor_gt           0.0461
_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)+(0.0374P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                1209
_reflns_number_total             3576
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25562f.txt
_cod_data_source_block           ko
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        972.3(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7208692
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
Na2 Na 0.0000 0.0000 0.0000 0.0529(6) Uani 1 2 d S
O3 O 0.0001(5) 0.1049(3) 0.1824(2) 0.0596(8) Uani 1 1 d .
O1 O 0.2793(4) -0.0552(3) 0.1068(2) 0.0564(8) Uani 1 1 d .
O2 O 0.2697(5) 0.0355(3) 0.2813(2) 0.0673(9) Uani 1 1 d .
H2 H 0.1881 0.0623 0.2516 0.11(2) Uiso 1 1 calc R
O6 O 0.2962(4) 0.1774(3) 0.0482(2) 0.0579(8) Uani 1 1 d .
O5 O 0.5362(5) 0.3217(3) 0.2033(2) 0.0708(9) Uani 1 1 d .
H5B H 0.5907 0.2670 0.1931 0.13(3) Uiso 1 1 calc R
C2 C 0.5020(7) -0.0779(4) 0.2532(4) 0.0554(11) Uani 1 1 d .
C9 C -0.0372(7) 0.2482(4) 0.3463(3) 0.0494(11) Uani 1 1 d .
C14 C -0.1787(7) 0.2706(4) 0.4062(3) 0.0585(12) Uani 1 1 d .
H14A H -0.3213 0.2324 0.3710 0.070 Uiso 1 1 calc R
C8 C -0.1144(7) 0.1633(4) 0.2258(3) 0.0522(11) Uani 1 1 d .
C16 C 0.2505(7) 0.3754(4) 0.1346(3) 0.0539(11) Uani 1 1 d .
C10 C 0.1735(7) 0.3087(4) 0.3997(3) 0.0576(12) Uani 1 1 d .
H10A H 0.2700 0.2952 0.3605 0.069 Uiso 1 1 calc R
C1 C 0.3413(7) -0.0321(4) 0.2063(4) 0.0540(11) Uani 1 1 d .
C15 C 0.3605(7) 0.2817(4) 0.1242(4) 0.0527(11) Uani 1 1 d .
C12 C 0.1033(8) 0.4101(5) 0.5704(4) 0.0652(13) Uani 1 1 d .
H12A H 0.1505 0.4643 0.6451 0.078 Uiso 1 1 calc R
C11 C 0.2426(8) 0.3892(5) 0.5111(4) 0.0679(13) Uani 1 1 d .
H11A H 0.3850 0.4294 0.5458 0.082 Uiso 1 1 calc R
C17 C 0.3523(8) 0.4998(5) 0.2049(4) 0.0676(13) Uani 1 1 d .
H17A H 0.4924 0.5262 0.2446 0.081 Uiso 1 1 calc R
C7 C 0.5655(8) -0.0513(5) 0.3648(4) 0.0783(16) Uani 1 1 d .
H7A H 0.5062 -0.0041 0.4130 0.094 Uiso 1 1 calc R
C13 C -0.1084(8) 0.3498(4) 0.5183(4) 0.0638(13) Uani 1 1 d .
H13A H -0.2038 0.3623 0.5585 0.077 Uiso 1 1 calc R
C21 C 0.0401(7) 0.3363(5) 0.0757(4) 0.0654(13) Uani 1 1 d .
H21A H -0.0288 0.2531 0.0279 0.078 Uiso 1 1 calc R
C3 C 0.5938(8) -0.1469(5) 0.1835(4) 0.0735(15) Uani 1 1 d .
H3A H 0.5508 -0.1669 0.1076 0.088 Uiso 1 1 calc R
C20 C -0.0660(8) 0.4225(6) 0.0892(5) 0.0757(14) Uani 1 1 d .
H20A H -0.2069 0.3967 0.0513 0.091 Uiso 1 1 calc R
C4 C 0.7501(9) -0.1864(6) 0.2264(5) 0.0911(19) Uani 1 1 d .
H4A H 0.8147 -0.2305 0.1793 0.109 Uiso 1 1 calc R
C19 C 0.0375(10) 0.5458(6) 0.1586(5) 0.0812(16) Uani 1 1 d .
H19A H -0.0336 0.6032 0.1667 0.097 Uiso 1 1 calc R
C18 C 0.2446(9) 0.5845(5) 0.2160(4) 0.0751(14) Uani 1 1 d .
H18A H 0.3132 0.6681 0.2625 0.090 Uiso 1 1 calc R
C6 C 0.7177(10) -0.0944(6) 0.4057(5) 0.0962(19) Uani 1 1 d .
H6A H 0.7575 -0.0776 0.4810 0.115 Uiso 1 1 calc R
C5 C 0.8096(9) -0.1614(6) 0.3365(6) 0.0933(18) Uani 1 1 d .
H5A H 0.9123 -0.1897 0.3645 0.112 Uiso 1 1 calc R
Na1 Na 0.5000 0.0000 0.0000 0.0635(7) Uani 1 2 d S
O4 O -0.2938(5) 0.1510(3) 0.1685(2) 0.0598(8) Uani 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'
Na Na 0.0362 0.0249 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Na1 O4 83.59(11) . 1_655 yes
O1 Na1 O4 96.41(11) . 2_555 yes
O1 Na1 O1 180.00 . 2_655 yes
O4 Na1 O4 180.00 1_655 2_555 yes
O1 Na1 O4 96.41(11) 2_655 1_655 yes
O1 Na1 O4 83.59(11) 2_655 2_555 yes
O1 Na2 O3 78.96(11) . . yes
O1 Na2 O6 79.51(11) . . yes
O1 Na2 O1 180.00 . 2_555 yes
O1 Na2 O3 101.04(11) . 2_555 yes
O1 Na2 O6 100.49(11) . 2_555 yes
O3 Na2 O6 82.79(11) . . yes
O1 Na2 O3 101.04(11) 2_555 . yes
O3 Na2 O3 180.00 . 2_555 yes
O3 Na2 O6 97.21(11) . 2_555 yes
O1 Na2 O6 100.49(11) 2_555 . yes
O3 Na2 O6 97.21(11) 2_555 . yes
O6 Na2 O6 180.00 . 2_555 yes
O1 Na2 O3 78.96(11) 2_555 2_555 yes
O1 Na2 O6 79.51(11) 2_555 2_555 yes
O3 Na2 O6 82.79(11) 2_555 2_555 yes
Na1 O1 Na2 88.43(10) . . yes
Na1 O1 C1 124.2(3) . . yes
Na2 O1 C1 131.4(3) . . yes
Na2 O3 C8 134.1(3) . . yes
Na1 O4 C8 129.9(3) 1_455 . yes
Na2 O6 C15 132.2(3) . . yes
C1 O2 H2 109.00 . . no
C15 O5 H5B 109.00 . . no
O1 C1 C2 123.6(4) . . yes
O1 C1 O2 122.8(4) . . yes
O2 C1 C2 113.7(4) . . yes
C3 C2 C7 118.8(5) . . no
C1 C2 C3 119.3(4) . . no
C1 C2 C7 121.9(5) . . no
C2 C3 C4 120.1(5) . . no
C3 C4 C5 120.6(6) . . no
C4 C5 C6 119.5(6) . . no
C5 C6 C7 120.7(6) . . no
C2 C7 C6 120.2(5) . . no
O4 C8 C9 119.4(4) . . yes
O3 C8 O4 121.3(3) . . yes
O3 C8 C9 119.3(4) . . yes
C8 C9 C10 121.4(4) . . no
C8 C9 C14 119.9(4) . . no
C10 C9 C14 118.7(4) . . no
C9 C10 C11 120.7(4) . . no
C10 C11 C12 120.6(5) . . no
C11 C12 C13 119.4(5) . . no
C12 C13 C14 120.2(5) . . no
C9 C14 C13 120.4(4) . . no
O5 C15 O6 122.7(5) . . yes
O5 C15 C16 113.6(4) . . yes
O6 C15 C16 123.8(4) . . yes
C15 C16 C17 120.9(4) . . no
C17 C16 C21 119.8(5) . . no
C15 C16 C21 119.3(4) . . no
C16 C17 C18 119.8(5) . . no
C17 C18 C19 120.4(6) . . no
C18 C19 C20 120.5(6) . . no
C19 C20 C21 120.1(6) . . no
C16 C21 C20 119.5(5) . . no
C2 C3 H3A 120.00 . . no
C4 C3 H3A 120.00 . . no
C3 C4 H4A 120.00 . . no
C5 C4 H4A 120.00 . . no
C4 C5 H5A 120.00 . . no
C6 C5 H5A 120.00 . . no
C5 C6 H6A 120.00 . . no
C7 C6 H6A 120.00 . . no
C2 C7 H7A 120.00 . . no
C6 C7 H7A 120.00 . . no
C9 C10 H10A 120.00 . . no
C11 C10 H10A 120.00 . . no
C10 C11 H11A 120.00 . . no
C12 C11 H11A 120.00 . . no
C11 C12 H12A 120.00 . . no
C13 C12 H12A 120.00 . . no
C12 C13 H13A 120.00 . . no
C14 C13 H13A 120.00 . . no
C9 C14 H14A 120.00 . . no
C13 C14 H14A 120.00 . . no
C16 C17 H17A 120.00 . . no
C18 C17 H17A 120.00 . . no
C17 C18 H18A 120.00 . . no
C19 C18 H18A 120.00 . . no
C18 C19 H19A 120.00 . . no
C20 C19 H19A 120.00 . . no
C19 C20 H20A 120.00 . . no
C21 C20 H20A 120.00 . . no
C16 C21 H21A 120.00 . . no
C20 C21 H21A 120.00 . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Na1 O1 2.399(3) . yes
Na1 O4 2.281(3) 1_655 yes
Na1 O4 2.281(3) 2_555 yes
Na1 O1 2.399(3) 2_655 yes
Na2 O1 2.540(3) . yes
Na2 O3 2.333(3) . yes
Na2 O6 2.378(3) . yes
Na2 O1 2.540(3) 2_555 yes
Na2 O3 2.333(3) 2_555 yes
Na2 O6 2.378(3) 2_555 yes
O1 C1 1.230(5) . yes
O2 C1 1.316(6) . yes
O3 C8 1.270(6) . yes
O4 C8 1.275(6) . yes
O5 C15 1.312(6) . yes
O6 C15 1.229(6) . yes
O2 H2 0.8200 . no
O5 H5B 0.8200 . no
C1 C2 1.484(7) . no
C2 C7 1.374(7) . no
C2 C3 1.379(7) . no
C3 C4 1.388(9) . no
C4 C5 1.358(9) . no
C5 C6 1.364(10) . no
C6 C7 1.385(9) . no
C8 C9 1.493(5) . no
C9 C14 1.389(7) . no
C9 C10 1.382(7) . no
C10 C11 1.386(6) . no
C11 C12 1.368(8) . no
C12 C13 1.385(8) . no
C13 C14 1.389(6) . no
C15 C16 1.489(7) . no
C16 C21 1.395(7) . no
C16 C17 1.387(7) . no
C17 C18 1.386(9) . no
C18 C19 1.371(9) . no
C19 C20 1.376(10) . no
C20 C21 1.392(9) . no
C3 H3A 0.9300 . no
C4 H4A 0.9300 . no
C5 H5A 0.9300 . no
C6 H6A 0.9300 . no
C7 H7A 0.9300 . no
C10 H10A 0.9300 . no
C11 H11A 0.9300 . no
C12 H12A 0.9300 . no
C13 H13A 0.9300 . no
C14 H14A 0.9300 . no
C17 H17A 0.9300 . no
C18 H18A 0.9300 . no
C19 H19A 0.9300 . no
C20 H20A 0.9300 . no
C21 H21A 0.9300 . no
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
O2 H2 O3 0.82 1.73 2.551(4) 174.7 .
O5 H5B O4 0.82 1.74 2.558(5) 178.7 1_655
