# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_ID1215MAmonop_a
_audit_block_doi                 10.5517/ccdc.csd.cc2bk69f
_database_code_depnum_ccdc_archive 'CCDC 2161484'
loop_
_audit_author_name
_audit_author_address
'Srinivasan Karuppannan'
;Bharathiar University
India
;
_audit_update_record             
;
2022-03-23 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        2-acetoxybenzoicacid
_chemical_name_common            Aspirin
_chemical_melting_point          409
_chemical_formula_moiety         C9H8O4
_chemical_formula_sum            'C9 H8 O4'
_chemical_formula_weight         180.15

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.2633(15)
_cell_length_b                   6.5624(8)
_cell_length_c                   11.4726(14)
_cell_angle_alpha                90
_cell_angle_beta                 111.627(3)
_cell_angle_gamma                90
_cell_volume                     858.28(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6070
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      22.30

_exptl_crystal_description       platy
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   0.9980
_exptl_transmission_factor_max   0.9990
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.998
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'R.H.Blessing Acta Crystallogr.A 1995,51,33'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed micro focustube'
_diffrn_measurement_device_type  'Bruker APEX-III CMOS PHOTON DECTECTOR'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51801
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_av_R_equivalents  0.1492
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.572
_diffrn_reflns_theta_max         27.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1915
_reflns_number_gt                1016
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL AND ENCIFER'
_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)+(0.0986P)²+0.4457P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1915
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1545
_refine_ls_R_factor_gt           0.0748
_refine_ls_wR_factor_ref         0.2056
_refine_ls_wR_factor_gt          0.1681
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.78414(19) 0.5882(4) 0.72717(18) 0.0494(7) Uani 1 1 d . . . . .
O2 O 0.6191(2) 0.8595(4) 0.6088(2) 0.0569(7) Uani 1 1 d . . . . .
H2 H 0.570366 0.949210 0.600880 0.085 Uiso 1 1 calc R U . . .
O1 O 0.5101(2) 0.8103(4) 0.4082(2) 0.0593(7) Uani 1 1 d . . . . .
O4 O 0.9040(2) 0.7804(4) 0.6661(2) 0.0618(8) Uani 1 1 d . . . . .
C7 C 0.5902(3) 0.7557(5) 0.5058(3) 0.0363(8) Uani 1 1 d . . . . .
C1 C 0.6534(3) 0.5644(5) 0.5073(3) 0.0389(8) Uani 1 1 d . . . . .
C8 C 0.8650(3) 0.7404(5) 0.7439(3) 0.0448(8) Uani 1 1 d . . . . .
C2 C 0.7452(3) 0.4867(5) 0.6110(3) 0.0441(8) Uani 1 1 d . . . . .
C6 C 0.6182(3) 0.4494(5) 0.3979(3) 0.0468(9) Uani 1 1 d . . . . .
H6 H 0.557147 0.496702 0.327348 0.056 Uiso 1 1 calc R U . . .
C5 C 0.6714(3) 0.2669(5) 0.3912(3) 0.0518(9) Uani 1 1 d . . . . .
H5 H 0.646873 0.192119 0.317169 0.062 Uiso 1 1 calc R U . . .
C3 C 0.7978(3) 0.3031(6) 0.6048(3) 0.0539(10) Uani 1 1 d . . . . .
H3 H 0.857916 0.251764 0.674751 0.065 Uiso 1 1 calc R U . . .
C4 C 0.7604(3) 0.1984(6) 0.4946(4) 0.0576(10) Uani 1 1 d . . . . .
H4 H 0.796800 0.076005 0.490018 0.069 Uiso 1 1 calc R U . . .
C9 C 0.8958(4) 0.8347(8) 0.8687(3) 0.0741(13) Uani 1 1 d . . . . .
H9A H 0.943935 0.952422 0.874373 0.111 Uiso 1 1 calc R U . . .
H9B H 0.937945 0.738249 0.932248 0.111 Uiso 1 1 calc R U . . .
H9C H 0.825371 0.874887 0.880813 0.111 Uiso 1 1 calc R U . . .


_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
O3 C8 1.370(4) . ?
O3 C2 1.407(4) . ?
O2 C7 1.295(4) . ?
O2 H2 0.8200 . ?
O1 C7 1.240(4) . ?
O4 C8 1.187(4) . ?
C7 C1 1.472(4) . ?
C1 C6 1.390(4) . ?
C1 C2 1.399(4) . ?
C8 C9 1.477(5) . ?
C2 C3 1.381(5) . ?
C6 C5 1.380(5) . ?
C6 H6 0.9300 . ?
C5 C4 1.359(5) . ?
C5 H5 0.9300 . ?
C3 C4 1.361(5) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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
C8 O3 C2 116.9(2) . . ?
C7 O2 H2 109.5 . . ?
O1 C7 O2 122.1(3) . . ?
O1 C7 C1 119.7(3) . . ?
O2 C7 C1 118.2(3) . . ?
C6 C1 C2 117.0(3) . . ?
C6 C1 C7 117.8(3) . . ?
C2 C1 C7 125.2(3) . . ?
O4 C8 O3 121.8(3) . . ?
O4 C8 C9 127.4(3) . . ?
O3 C8 C9 110.7(3) . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 O3 117.4(3) . . ?
C1 C2 O3 121.2(3) . . ?
C5 C6 C1 121.7(3) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
C4 C5 C6 118.9(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 122.1(4) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
O1 C7 C1 C6 -1.3(4) . . . . ?
O2 C7 C1 C6 177.1(3) . . . . ?
O1 C7 C1 C2 179.8(3) . . . . ?
O2 C7 C1 C2 -1.7(4) . . . . ?
C2 O3 C8 O4 -2.7(5) . . . . ?
C2 O3 C8 C9 179.0(3) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C7 C1 C2 C3 178.5(3) . . . . ?
C6 C1 C2 O3 -177.6(3) . . . . ?
C7 C1 C2 O3 1.3(5) . . . . ?
C8 O3 C2 C3 97.8(3) . . . . ?
C8 O3 C2 C1 -84.9(3) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
C7 C1 C6 C5 -179.2(3) . . . . ?
C1 C6 C5 C4 0.2(5) . . . . ?
C1 C2 C3 C4 1.1(5) . . . . ?
O3 C2 C3 C4 178.4(3) . . . . ?
C6 C5 C4 C3 0.6(6) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?

_refine_diff_density_max         0.514
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.058


_exptl_crystal_recrystallization_method 'Solution Crystallization process'
_chemical_properties_physical    Hygroscopic
####################################################################### 
# 
# 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_ASAMONOP_a
_audit_block_doi                 10.5517/ccdc.csd.cc2bnj5q
_database_code_depnum_ccdc_archive 'CCDC 2164673'
loop_
_audit_author_name
_audit_author_address
'Srinivasan Karuppannan'
;Bharathiar University
India
;
_audit_update_record             
;
2022-04-06 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        2-acetoxybenzoicacid
_chemical_name_common            'Acetylsalicylic acid'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 04'
_chemical_formula_sum            'C9 H8 O4'
_chemical_formula_weight         180.15

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.429(4)
_cell_length_b                   6.597(2)
_cell_length_c                   11.395(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.750(9)
_cell_angle_gamma                90
_cell_volume                     854.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6570
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      22.47

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   0.9500
_exptl_transmission_factor_max   0.9970
_exptl_crystal_size_max          0.463
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'B.H.Blessings,Acta CrystalograA,1995,51,33'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Microfocus Tube'
_diffrn_measurement_device_type  'Bruker APEX-III CMOS Photon Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45382
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_av_R_equivalents  0.1422
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.570
_diffrn_reflns_theta_max         27.442
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1946
_reflns_number_gt                1141
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and Encifer'
_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)+(0.0494P)²+0.2533P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1946
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1245
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.21473(12) 0.4113(2) 0.58794(11) 0.0410(4) Uani 1 1 d . . . . .
O1 O 0.37983(13) 0.1402(2) 0.55085(14) 0.0513(5) Uani 1 1 d . . . . .
H1 H 0.424304 0.043231 0.563006 0.077 Uiso 1 1 calc R U . . .
O2 O 0.48955(14) 0.1880(2) 0.40343(13) 0.0528(5) Uani 1 1 d . . . . .
O4 O 0.09651(15) 0.2205(3) 0.46551(13) 0.0614(5) Uani 1 1 d . . . . .
C7 C 0.40975(17) 0.2429(3) 0.46213(16) 0.0355(5) Uani 1 1 d . . . . .
C1 C 0.34702(17) 0.4357(3) 0.43238(17) 0.0349(5) Uani 1 1 d . . . . .
C2 C 0.25423(18) 0.5122(3) 0.49045(16) 0.0369(5) Uani 1 1 d . . . . .
C6 C 0.38307(18) 0.5501(3) 0.34026(18) 0.0414(5) Uani 1 1 d . . . . .
H6 H 0.444634 0.503086 0.300116 0.050 Uiso 1 1 calc R U . . .
C8 C 0.13424(19) 0.2617(3) 0.56368(18) 0.0411(5) Uani 1 1 d . . . . .
C3 C 0.20213(19) 0.6940(3) 0.4584(2) 0.0473(6) Uani 1 1 d . . . . .
H3 H 0.141326 0.743686 0.498672 0.057 Uiso 1 1 calc R U . . .
C5 C 0.3300(2) 0.7312(3) 0.3068(2) 0.0486(6) Uani 1 1 d . . . . .
H5 H 0.354860 0.804659 0.244240 0.058 Uiso 1 1 calc R U . . .
C4 C 0.2402(2) 0.8023(4) 0.3665(2) 0.0507(6) Uani 1 1 d . . . . .
H4 H 0.204655 0.925207 0.344605 0.061 Uiso 1 1 calc R U . . .
C9 C 0.1029(2) 0.1634(4) 0.6731(2) 0.0603(7) Uani 1 1 d . . . . .
H9A H 0.047722 0.056069 0.653217 0.090 Uiso 1 1 calc R U . . .
H9B H 0.068252 0.261654 0.721164 0.090 Uiso 1 1 calc R U . . .
H9C H 0.172495 0.108610 0.715717 0.090 Uiso 1 1 calc R U . . .


_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
O3 C8 1.359(3) . ?
O3 C2 1.408(2) . ?
O1 C7 1.292(2) . ?
O1 H1 0.8200 . ?
O2 C7 1.238(2) . ?
O4 C8 1.189(2) . ?
C7 C1 1.483(3) . ?
C1 C6 1.388(3) . ?
C1 C2 1.399(3) . ?
C2 C3 1.372(3) . ?
C6 C5 1.377(3) . ?
C6 H6 0.9300 . ?
C8 C9 1.480(3) . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C5 C4 1.369(3) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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
C8 O3 C2 116.55(15) . . ?
C7 O1 H1 109.5 . . ?
O2 C7 O1 122.44(19) . . ?
O2 C7 C1 119.55(18) . . ?
O1 C7 C1 118.00(17) . . ?
C6 C1 C2 117.27(19) . . ?
C6 C1 C7 117.75(17) . . ?
C2 C1 C7 124.98(18) . . ?
C3 C2 C1 121.23(19) . . ?
C3 C2 O3 117.27(18) . . ?
C1 C2 O3 121.41(18) . . ?
C5 C6 C1 121.66(19) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
O4 C8 O3 122.11(19) . . ?
O4 C8 C9 126.6(2) . . ?
O3 C8 C9 111.27(18) . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C4 C5 C6 119.4(2) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
O2 C7 C1 C6 -1.5(3) . . . . ?
O1 C7 C1 C6 177.19(19) . . . . ?
O2 C7 C1 C2 178.78(19) . . . . ?
O1 C7 C1 C2 -2.5(3) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C7 C1 C2 C3 178.96(19) . . . . ?
C6 C1 C2 O3 -177.37(17) . . . . ?
C7 C1 C2 O3 2.4(3) . . . . ?
C8 O3 C2 C3 97.9(2) . . . . ?
C8 O3 C2 C1 -85.4(2) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C7 C1 C6 C5 -179.85(19) . . . . ?
C2 O3 C8 O4 -1.8(3) . . . . ?
C2 O3 C8 C9 178.11(18) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
O3 C2 C3 C4 177.7(2) . . . . ?
C1 C6 C5 C4 0.8(3) . . . . ?
C6 C5 C4 C3 -0.6(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.040


_exptl_crystal_recrystallization_method 'Solution-state crystallization method'
_chemical_properties_physical    Hygroscopic
