# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_acido_usnico_0m
_database_code_depnum_ccdc_archive 'CCDC 1033509'
_audit_update_record             
;
2014-11-10 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;

_audit_creation_date             2014-11-10T11:26:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        'usnic acid'
_chemical_formula_moiety         'C18 H16 O7'
_chemical_formula_sum            'C18 H16 O7'
_chemical_formula_weight         344.31
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.0077(3)
_cell_length_b                   18.8247(6)
_cell_length_c                   20.1978(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3044.67(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9992
_cell_measurement_theta_max      3.209
_cell_measurement_theta_min      66.9
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.081
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_max          0.602
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_F_000             1440
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.987
_exptl_absorpt_correction_T_min  0.9345
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_number            37959
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.209
_diffrn_reflns_theta_max         67.229
_diffrn_reflns_theta_full        67.679
_diffrn_measurement_device_type  'APEX II CCD detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.977
_reflns_number_total             5346
_reflns_number_gt                5300
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0406P)²+0.5283P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5346
_refine_ls_number_parameters     471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.063
_refine_ls_wR_factor_gt          0.0628
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 2266 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.026(18)
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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_
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
H1SA H 0.381(5) 0.3048(19) 0.5137(18) 0.087(11) Uiso 1 d . .
H1SB H -0.254(5) 0.555(2) 1.037(2) 0.103(13) Uiso 1 d . .
O1A O -0.08692(15) 0.40279(6) 0.69539(5) 0.0202(2) Uani 1 d . .
O14A O 0.28578(17) 0.35362(7) 0.52167(6) 0.0282(3) Uani 1 d . .
O16A O 0.46367(18) 0.25108(7) 0.52727(6) 0.0318(3) Uani 1 d . .
O17A O 0.18860(15) 0.18851(6) 0.69391(6) 0.0216(2) Uani 1 d . .
O19A O 0.01190(16) 0.18755(6) 0.80530(6) 0.0249(3) Uani 1 d . .
H19A H 0.0698 0.1824 0.771 0.037 Uiso 1 calc . .
O21A O -0.29322(16) 0.36265(7) 0.91825(6) 0.0261(3) Uani 1 d . .
H21A H -0.3333 0.4035 0.9133 0.039 Uiso 1 calc . .
O21B O 0.49770(16) 0.34989(7) 0.69570(6) 0.0279(3) Uani 1 d . .
H21B H 0.4989 0.3825 0.6673 0.042 Uiso 1 calc . .
O23A O -0.34969(15) 0.48157(7) 0.86311(6) 0.0277(3) Uani 1 d . .
C2A C 0.0033(2) 0.35957(9) 0.65494(8) 0.0180(3) Uani 1 d . .
C3A C 0.0857(2) 0.38102(9) 0.60090(8) 0.0217(4) Uani 1 d . .
H3A H 0.0663 0.4264 0.5818 0.026 Uiso 1 calc . .
C4A C 0.2052(2) 0.33228(9) 0.57301(8) 0.0209(4) Uani 1 d . .
C5A C 0.2470(2) 0.26575(9) 0.60375(8) 0.0191(3) Uani 1 d . .
C6A C 0.1579(2) 0.24319(9) 0.66154(8) 0.0170(3) Uani 1 d . .
C7A C 0.0026(2) 0.28501(8) 0.68005(8) 0.0168(3) Uani 1 d . .
C8A C -0.04069(19) 0.29889(9) 0.75188(8) 0.0170(3) Uani 1 d . .
C9A C -0.0510(2) 0.25372(9) 0.80682(8) 0.0193(3) Uani 1 d . .
C10A C -0.1326(2) 0.27718(9) 0.86399(8) 0.0217(4) Uani 1 d . .
C11A C -0.2058(2) 0.34463(9) 0.86396(8) 0.0205(3) Uani 1 d . .
C12A C -0.1925(2) 0.39331(9) 0.81006(8) 0.0196(3) Uani 1 d . .
C13A C -0.1071(2) 0.36582(9) 0.75528(8) 0.0170(3) Uani 1 d . .
C15A C 0.3895(2) 0.22791(9) 0.57836(8) 0.0216(4) Uani 1 d . .
C18A C -0.1471(2) 0.24517(10) 0.64683(8) 0.0226(4) Uani 1 d . .
H18A H -0.2501 0.2723 0.6538 0.034 Uiso 1 calc . .
H18B H -0.1588 0.1979 0.6666 0.034 Uiso 1 calc . .
H18C H -0.1261 0.2404 0.5992 0.034 Uiso 1 calc . .
C20A C -0.1485(3) 0.22961(11) 0.92368(9) 0.0291(4) Uani 1 d . .
H20A H -0.0889 0.185 0.9155 0.044 Uiso 1 calc . .
H20B H -0.2667 0.2195 0.932 0.044 Uiso 1 calc . .
H20C H -0.1003 0.2534 0.9624 0.044 Uiso 1 calc . .
C22A C -0.2685(2) 0.46376(9) 0.81353(8) 0.0216(4) Uani 1 d . .
C24A C 0.4608(2) 0.16308(10) 0.60953(9) 0.0251(4) Uani 1 d . .
H24A H 0.5605 0.1482 0.5851 0.038 Uiso 1 calc . .
H24B H 0.3777 0.1249 0.6085 0.038 Uiso 1 calc . .
H24C H 0.491 0.1734 0.6556 0.038 Uiso 1 calc . .
C25A C -0.2479(2) 0.51662(9) 0.75849(9) 0.0266(4) Uani 1 d . .
H25A H -0.31 0.56 0.7692 0.04 Uiso 1 calc . .
H25B H -0.291 0.4963 0.7172 0.04 Uiso 1 calc . .
H25C H -0.1292 0.528 0.7532 0.04 Uiso 1 calc . .
O1B O 0.18522(16) 0.52473(6) 0.82223(6) 0.0234(3) Uani 1 d . .
O14B O -0.18950(17) 0.58963(7) 0.99151(7) 0.0294(3) Uani 1 d . .
O16B O -0.28158(17) 0.50301(8) 1.07090(7) 0.0315(3) Uani 1 d . .
O17B O 0.07002(16) 0.36363(6) 0.98628(6) 0.0225(3) Uani 1 d . .
O19B O 0.29632(16) 0.29868(6) 0.90890(6) 0.0236(3) Uani 1 d . .
H19B H 0.2337 0.3156 0.9383 0.035 Uiso 1 calc . .
O23B O 0.43006(18) 0.46772(8) 0.64258(7) 0.0357(3) Uani 1 d . .
C15B C -0.1785(2) 0.45707(10) 1.04906(8) 0.0236(4) Uani 1 d . .
C18B C 0.3285(2) 0.47961(10) 0.96543(9) 0.0231(4) Uani 1 d . .
H18D H 0.4124 0.5042 0.9386 0.035 Uiso 1 calc . .
H18E H 0.3785 0.4373 0.9856 0.035 Uiso 1 calc . .
H18F H 0.2882 0.5115 1.0003 0.035 Uiso 1 calc . .
C20B C 0.4730(2) 0.25109(10) 0.79869(9) 0.0265(4) Uani 1 d . .
H20D H 0.3874 0.2162 0.7867 0.04 Uiso 1 calc . .
H20E H 0.52 0.2389 0.842 0.04 Uiso 1 calc . .
H20F H 0.5619 0.2507 0.7653 0.04 Uiso 1 calc . .
C22B C 0.3501(2) 0.48708(11) 0.69180(9) 0.0294(4) Uani 1 d . .
C24B C -0.1821(3) 0.38610(11) 1.08078(9) 0.0317(4) Uani 1 d . .
H24D H -0.2594 0.3869 1.1184 0.048 Uiso 1 calc . .
H24E H -0.0699 0.3738 1.0964 0.048 Uiso 1 calc . .
H24F H -0.2195 0.3506 1.0485 0.048 Uiso 1 calc . .
C25B C 0.2672(3) 0.55828(14) 0.69002(12) 0.0524(7) Uani 1 d . .
H25D H 0.2844 0.58 0.6465 0.079 Uiso 1 calc . .
H25E H 0.3155 0.5888 0.7243 0.079 Uiso 1 calc . .
H25F H 0.1473 0.5526 0.6981 0.079 Uiso 1 calc . .
C2B C 0.1145(2) 0.52021(9) 0.88394(8) 0.0197(3) Uani 1 d . .
C3B C -0.0015(2) 0.56434(9) 0.90669(9) 0.0222(4) Uani 1 d . .
H3B H -0.0279 0.6072 0.8841 0.027 Uiso 1 calc . .
C4B C -0.0860(2) 0.54448(9) 0.96725(8) 0.0211(3) Uani 1 d . .
C5B C -0.0684(2) 0.47521(9) 0.99594(8) 0.0194(3) Uani 1 d . .
C6B C 0.0526(2) 0.42604(9) 0.96885(8) 0.0180(3) Uani 1 d . .
C7B C 0.1789(2) 0.45693(9) 0.92045(8) 0.0181(3) Uani 1 d . .
C8B C 0.2429(2) 0.41347(9) 0.86267(8) 0.0182(3) Uani 1 d . .
C9B C 0.3097(2) 0.34508(9) 0.85882(8) 0.0191(3) Uani 1 d . .
C10B C 0.3959(2) 0.32388(9) 0.80177(8) 0.0205(3) Uani 1 d . .
C11B C 0.4101(2) 0.37137(10) 0.74925(8) 0.0223(4) Uani 1 d . .
C12B C 0.3367(2) 0.44097(10) 0.74980(8) 0.0224(4) Uani 1 d . .
C13B C 0.2565(2) 0.45813(9) 0.80922(8) 0.0196(3) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O1A C2A 1.361(2) . ?
O1A C13A 1.405(2) . ?
O14A C4A 1.286(2) . ?
O14A H1SA 1.20(4) . ?
O16A C15A 1.268(2) . ?
O16A H1SA 1.24(4) . ?
O17A C6A 1.244(2) . ?
O19A C9A 1.344(2) . ?
O19A H19A 0.84 . ?
O21A C11A 1.345(2) . ?
O21A H21A 0.84 . ?
O21B C11B 1.351(2) . ?
O21B H21B 0.84 . ?
O23A C22A 1.240(2) . ?
C2A C3A 1.338(2) . ?
C2A C7A 1.492(2) . ?
C3A C4A 1.440(3) . ?
C3A H3A 0.95 . ?
C4A C5A 1.437(2) . ?
C5A C6A 1.432(2) . ?
C5A C15A 1.440(2) . ?
C6A C7A 1.519(2) . ?
C7A C8A 1.514(2) . ?
C7A C18A 1.565(2) . ?
C8A C13A 1.369(2) . ?
C8A C9A 1.401(2) . ?
C9A C10A 1.398(2) . ?
C10A C11A 1.398(3) . ?
C10A C20A 1.507(2) . ?
C11A C12A 1.427(2) . ?
C12A C13A 1.400(2) . ?
C12A C22A 1.461(2) . ?
C15A C24A 1.487(3) . ?
C18A H18A 0.98 . ?
C18A H18B 0.98 . ?
C18A H18C 0.98 . ?
C20A H20A 0.98 . ?
C20A H20B 0.98 . ?
C20A H20C 0.98 . ?
C22A C25A 1.501(3) . ?
C24A H24A 0.98 . ?
C24A H24B 0.98 . ?
C24A H24C 0.98 . ?
C25A H25A 0.98 . ?
C25A H25B 0.98 . ?
C25A H25C 0.98 . ?
O1B C2B 1.372(2) . ?
O1B C13B 1.402(2) . ?
O14B C4B 1.284(2) . ?
O14B H1SB 1.23(4) . ?
O16B C15B 1.274(2) . ?
O16B H1SB 1.22(4) . ?
O17B C6B 1.234(2) . ?
O19B C9B 1.341(2) . ?
O19B H19B 0.84 . ?
O23B C22B 1.237(2) . ?
C15B C5B 1.430(3) . ?
C15B C24B 1.482(3) . ?
C18B C7B 1.563(2) . ?
C18B H18D 0.98 . ?
C18B H18E 0.98 . ?
C18B H18F 0.98 . ?
C20B C10B 1.504(3) . ?
C20B H20D 0.98 . ?
C20B H20E 0.98 . ?
C20B H20F 0.98 . ?
C22B C12B 1.462(3) . ?
C22B C25B 1.496(3) . ?
C24B H24D 0.98 . ?
C24B H24E 0.98 . ?
C24B H24F 0.98 . ?
C25B H25D 0.98 . ?
C25B H25E 0.98 . ?
C25B H25F 0.98 . ?
C2B C3B 1.328(3) . ?
C2B C7B 1.493(2) . ?
C3B C4B 1.447(3) . ?
C3B H3B 0.95 . ?
C4B C5B 1.434(2) . ?
C5B C6B 1.447(2) . ?
C6B C7B 1.522(2) . ?
C7B C8B 1.515(2) . ?
C8B C13B 1.373(2) . ?
C8B C9B 1.396(2) . ?
C9B C10B 1.401(2) . ?
C10B C11B 1.392(3) . ?
C11B C12B 1.436(3) . ?
C12B C13B 1.399(2) . ?

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
C2A O1A C13A 106.37(12) . . ?
C4A O14A H1SA 100.7(17) . . ?
C15A O16A H1SA 102.1(17) . . ?
C9A O19A H19A 109.5 . . ?
C11A O21A H21A 109.5 . . ?
C11B O21B H21B 109.5 . . ?
C3A C2A O1A 124.85(15) . . ?
C3A C2A C7A 124.25(15) . . ?
O1A C2A C7A 110.87(13) . . ?
C2A C3A C4A 117.04(15) . . ?
C2A C3A H3A 121.5 . . ?
C4A C3A H3A 121.5 . . ?
O14A C4A C5A 120.26(16) . . ?
O14A C4A C3A 116.73(15) . . ?
C5A C4A C3A 122.73(15) . . ?
C6A C5A C4A 119.63(15) . . ?
C6A C5A C15A 122.57(15) . . ?
C4A C5A C15A 117.51(15) . . ?
O17A C6A C5A 125.12(15) . . ?
O17A C6A C7A 117.46(14) . . ?
C5A C6A C7A 117.05(14) . . ?
C2A C7A C8A 99.45(13) . . ?
C2A C7A C6A 113.62(14) . . ?
C8A C7A C6A 120.83(13) . . ?
C2A C7A C18A 107.94(14) . . ?
C8A C7A C18A 108.56(13) . . ?
C6A C7A C18A 105.87(13) . . ?
C13A C8A C9A 119.74(15) . . ?
C13A C8A C7A 107.20(14) . . ?
C9A C8A C7A 131.90(15) . . ?
O19A C9A C10A 119.14(15) . . ?
O19A C9A C8A 121.50(15) . . ?
C10A C9A C8A 119.34(16) . . ?
C9A C10A C11A 118.84(15) . . ?
C9A C10A C20A 120.82(16) . . ?
C11A C10A C20A 120.29(16) . . ?
O21A C11A C10A 116.55(15) . . ?
O21A C11A C12A 119.93(16) . . ?
C10A C11A C12A 123.52(15) . . ?
C13A C12A C11A 113.70(15) . . ?
C13A C12A C22A 125.24(15) . . ?
C11A C12A C22A 121.03(15) . . ?
C8A C13A C12A 124.71(15) . . ?
C8A C13A O1A 111.60(14) . . ?
C12A C13A O1A 123.61(15) . . ?
O16A C15A C5A 119.40(16) . . ?
O16A C15A C24A 116.57(16) . . ?
C5A C15A C24A 124.01(15) . . ?
C7A C18A H18A 109.5 . . ?
C7A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C7A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C10A C20A H20A 109.5 . . ?
C10A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C10A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
O23A C22A C12A 120.16(16) . . ?
O23A C22A C25A 118.45(16) . . ?
C12A C22A C25A 121.38(15) . . ?
C15A C24A H24A 109.5 . . ?
C15A C24A H24B 109.5 . . ?
H24A C24A H24B 109.5 . . ?
C15A C24A H24C 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
C22A C25A H25A 109.5 . . ?
C22A C25A H25B 109.5 . . ?
H25A C25A H25B 109.5 . . ?
C22A C25A H25C 109.5 . . ?
H25A C25A H25C 109.5 . . ?
H25B C25A H25C 109.5 . . ?
C2B O1B C13B 106.42(13) . . ?
C4B O14B H1SB 101.9(19) . . ?
C15B O16B H1SB 103.6(19) . . ?
C9B O19B H19B 109.5 . . ?
O16B C15B C5B 119.80(16) . . ?
O16B C15B C24B 116.73(17) . . ?
C5B C15B C24B 123.47(16) . . ?
C7B C18B H18D 109.5 . . ?
C7B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C7B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C10B C20B H20D 109.5 . . ?
C10B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C10B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
O23B C22B C12B 120.48(18) . . ?
O23B C22B C25B 118.30(18) . . ?
C12B C22B C25B 121.22(17) . . ?
C15B C24B H24D 109.5 . . ?
C15B C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
C15B C24B H24F 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?
C22B C25B H25D 109.5 . . ?
C22B C25B H25E 109.5 . . ?
H25D C25B H25E 109.5 . . ?
C22B C25B H25F 109.5 . . ?
H25D C25B H25F 109.5 . . ?
H25E C25B H25F 109.5 . . ?
C3B C2B O1B 124.35(15) . . ?
C3B C2B C7B 124.72(16) . . ?
O1B C2B C7B 110.86(14) . . ?
C2B C3B C4B 117.26(16) . . ?
C2B C3B H3B 121.4 . . ?
C4B C3B H3B 121.4 . . ?
O14B C4B C5B 120.74(16) . . ?
O14B C4B C3B 116.96(16) . . ?
C5B C4B C3B 122.04(15) . . ?
C15B C5B C4B 117.36(15) . . ?
C15B C5B C6B 122.94(15) . . ?
C4B C5B C6B 119.65(15) . . ?
O17B C6B C5B 125.21(16) . . ?
O17B C6B C7B 118.14(15) . . ?
C5B C6B C7B 116.31(14) . . ?
C2B C7B C8B 99.63(13) . . ?
C2B C7B C6B 113.14(14) . . ?
C8B C7B C6B 120.90(14) . . ?
C2B C7B C18B 109.49(14) . . ?
C8B C7B C18B 109.62(14) . . ?
C6B C7B C18B 103.90(13) . . ?
C13B C8B C9B 119.37(15) . . ?
C13B C8B C7B 107.58(14) . . ?
C9B C8B C7B 132.12(15) . . ?
O19B C9B C8B 121.87(15) . . ?
O19B C9B C10B 118.32(15) . . ?
C8B C9B C10B 119.80(15) . . ?
C11B C10B C9B 118.96(16) . . ?
C11B C10B C20B 121.33(16) . . ?
C9B C10B C20B 119.71(15) . . ?
O21B C11B C10B 117.41(16) . . ?
O21B C11B C12B 119.46(16) . . ?
C10B C11B C12B 123.13(15) . . ?
C13B C12B C11B 113.90(15) . . ?
C13B C12B C22B 125.75(17) . . ?
C11B C12B C22B 120.34(16) . . ?
C8B C13B C12B 124.73(16) . . ?
C8B C13B O1B 111.59(14) . . ?
C12B C13B O1B 123.63(15) . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13A O1A C2A C3A -161.69(17) . . . . ?
C13A O1A C2A C7A 16.56(17) . . . . ?
O1A C2A C3A C4A 165.81(16) . . . . ?
C7A C2A C3A C4A -12.2(3) . . . . ?
C2A C3A C4A O14A -179.00(16) . . . . ?
C2A C3A C4A C5A -5.1(3) . . . . ?
O14A C4A C5A C6A 179.01(15) . . . . ?
C3A C4A C5A C6A 5.4(2) . . . . ?
O14A C4A C5A C15A 5.1(2) . . . . ?
C3A C4A C5A C15A -168.57(16) . . . . ?
C4A C5A C6A O17A -176.45(15) . . . . ?
C15A C5A C6A O17A -2.8(3) . . . . ?
C4A C5A C6A C7A 10.6(2) . . . . ?
C15A C5A C6A C7A -175.75(14) . . . . ?
C3A C2A C7A C8A 156.90(17) . . . . ?
O1A C2A C7A C8A -21.35(17) . . . . ?
C3A C2A C7A C6A 27.1(2) . . . . ?
O1A C2A C7A C6A -151.13(13) . . . . ?
C3A C2A C7A C18A -90.0(2) . . . . ?
O1A C2A C7A C18A 91.79(15) . . . . ?
O17A C6A C7A C2A 161.59(14) . . . . ?
C5A C6A C7A C2A -24.9(2) . . . . ?
O17A C6A C7A C8A 43.6(2) . . . . ?
C5A C6A C7A C8A -142.96(15) . . . . ?
O17A C6A C7A C18A -80.14(17) . . . . ?
C5A C6A C7A C18A 93.33(16) . . . . ?
C2A C7A C8A C13A 18.15(17) . . . . ?
C6A C7A C8A C13A 143.06(15) . . . . ?
C18A C7A C8A C13A -94.50(15) . . . . ?
C2A C7A C8A C9A -174.58(17) . . . . ?
C6A C7A C8A C9A -49.7(2) . . . . ?
C18A C7A C8A C9A 72.8(2) . . . . ?
C13A C8A C9A O19A 179.68(15) . . . . ?
C7A C8A C9A O19A 13.7(3) . . . . ?
C13A C8A C9A C10A 1.4(2) . . . . ?
C7A C8A C9A C10A -164.53(16) . . . . ?
O19A C9A C10A C11A -176.52(15) . . . . ?
C8A C9A C10A C11A 1.8(2) . . . . ?
O19A C9A C10A C20A 0.7(2) . . . . ?
C8A C9A C10A C20A 179.03(16) . . . . ?
C9A C10A C11A O21A 175.21(15) . . . . ?
C20A C10A C11A O21A -2.1(2) . . . . ?
C9A C10A C11A C12A -4.4(2) . . . . ?
C20A C10A C11A C12A 178.34(16) . . . . ?
O21A C11A C12A C13A -176.12(14) . . . . ?
C10A C11A C12A C13A 3.5(2) . . . . ?
O21A C11A C12A C22A 1.9(2) . . . . ?
C10A C11A C12A C22A -178.54(15) . . . . ?
C9A C8A C13A C12A -2.4(2) . . . . ?
C7A C8A C13A C12A 166.75(15) . . . . ?
C9A C8A C13A O1A -179.17(14) . . . . ?
C7A C8A C13A O1A -10.07(18) . . . . ?
C11A C12A C13A C8A 0.0(2) . . . . ?
C22A C12A C13A C8A -177.94(15) . . . . ?
C11A C12A C13A O1A 176.41(14) . . . . ?
C22A C12A C13A O1A -1.5(2) . . . . ?
C2A O1A C13A C8A -3.76(17) . . . . ?
C2A O1A C13A C12A 179.38(15) . . . . ?
C6A C5A C15A O16A -179.41(15) . . . . ?
C4A C5A C15A O16A -5.7(2) . . . . ?
C6A C5A C15A C24A -1.2(3) . . . . ?
C4A C5A C15A C24A 172.53(16) . . . . ?
C13A C12A C22A O23A 175.90(15) . . . . ?
C11A C12A C22A O23A -1.9(2) . . . . ?
C13A C12A C22A C25A -5.3(2) . . . . ?
C11A C12A C22A C25A 176.91(15) . . . . ?
C13B O1B C2B C3B -161.06(17) . . . . ?
C13B O1B C2B C7B 15.90(17) . . . . ?
O1B C2B C3B C4B 168.35(15) . . . . ?
C7B C2B C3B C4B -8.2(3) . . . . ?
C2B C3B C4B O14B 175.23(16) . . . . ?
C2B C3B C4B C5B -10.6(3) . . . . ?
O16B C15B C5B C4B -3.1(2) . . . . ?
C24B C15B C5B C4B 176.13(17) . . . . ?
O16B C15B C5B C6B 179.60(16) . . . . ?
C24B C15B C5B C6B -1.1(3) . . . . ?
O14B C4B C5B C15B 4.4(2) . . . . ?
C3B C4B C5B C15B -169.53(16) . . . . ?
O14B C4B C5B C6B -178.24(15) . . . . ?
C3B C4B C5B C6B 7.8(2) . . . . ?
C15B C5B C6B O17B 2.8(3) . . . . ?
C4B C5B C6B O17B -174.43(16) . . . . ?
C15B C5B C6B C7B -170.40(15) . . . . ?
C4B C5B C6B C7B 12.4(2) . . . . ?
C3B C2B C7B C8B 156.99(17) . . . . ?
O1B C2B C7B C8B -19.96(17) . . . . ?
C3B C2B C7B C6B 27.3(2) . . . . ?
O1B C2B C7B C6B -149.67(14) . . . . ?
C3B C2B C7B C18B -88.1(2) . . . . ?
O1B C2B C7B C18B 94.96(16) . . . . ?
O17B C6B C7B C2B 158.46(15) . . . . ?
C5B C6B C7B C2B -27.9(2) . . . . ?
O17B C6B C7B C8B 40.6(2) . . . . ?
C5B C6B C7B C8B -145.77(15) . . . . ?
O17B C6B C7B C18B -82.88(17) . . . . ?
C5B C6B C7B C18B 90.78(16) . . . . ?
C2B C7B C8B C13B 16.64(17) . . . . ?
C6B C7B C8B C13B 141.12(15) . . . . ?
C18B C7B C8B C13B -98.19(16) . . . . ?
C2B C7B C8B C9B -174.79(17) . . . . ?
C6B C7B C8B C9B -50.3(2) . . . . ?
C18B C7B C8B C9B 70.4(2) . . . . ?
C13B C8B C9B O19B -178.29(15) . . . . ?
C7B C8B C9B O19B 14.2(3) . . . . ?
C13B C8B C9B C10B 2.8(2) . . . . ?
C7B C8B C9B C10B -164.72(17) . . . . ?
O19B C9B C10B C11B 179.69(15) . . . . ?
C8B C9B C10B C11B -1.3(2) . . . . ?
O19B C9B C10B C20B -1.2(2) . . . . ?
C8B C9B C10B C20B 177.82(15) . . . . ?
C9B C10B C11B O21B 178.31(14) . . . . ?
C20B C10B C11B O21B -0.8(2) . . . . ?
C9B C10B C11B C12B -1.7(2) . . . . ?
C20B C10B C11B C12B 179.20(15) . . . . ?
O21B C11B C12B C13B -176.98(15) . . . . ?
C10B C11B C12B C13B 3.0(2) . . . . ?
O21B C11B C12B C22B 2.7(2) . . . . ?
C10B C11B C12B C22B -177.31(16) . . . . ?
O23B C22B C12B C13B 176.99(17) . . . . ?
C25B C22B C12B C13B -3.5(3) . . . . ?
O23B C22B C12B C11B -2.7(3) . . . . ?
C25B C22B C12B C11B 176.8(2) . . . . ?
C9B C8B C13B C12B -1.3(2) . . . . ?
C7B C8B C13B C12B 169.01(15) . . . . ?
C9B C8B C13B O1B -179.01(14) . . . . ?
C7B C8B C13B O1B -8.73(18) . . . . ?
C11B C12B C13B C8B -1.5(2) . . . . ?
C22B C12B C13B C8B 178.82(17) . . . . ?
C11B C12B C13B O1B 175.96(14) . . . . ?
C22B C12B C13B O1B -3.7(3) . . . . ?
C2B O1B C13B C8B -4.21(18) . . . . ?
C2B O1B C13B C12B 178.02(15) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_name_common            'usnic acid'
