# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Mike Hursthouse'
_publ_contact_author_email       MBH@SOTON.AC.UK

_publ_section_title              
;
Intriguing Relationships and Associations
in the Crystal Structures of a Family of Substituted Aspirin
Molecules
;
loop_
_publ_author_name
'Mike Hursthouse'
'Riccardo Montis'
'Graham J Tizzard'

# Attachment 'Asp_derivatives.cif'

data_shelxl1
_database_code_depnum_ccdc_archive 'CCDC 643150'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'2-acetyloxy-4-methylbenzoic acid'
;
_chemical_name_common            "'2-acetyloxy-4-methylbenzoic acid'"
_chemical_melting_point          135
_chemical_formula_moiety         'C10 H10 O4'
_chemical_formula_sum            'C10 H10 O4'
_chemical_formula_weight         194.18

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  -P2yn

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

_cell_length_a                   4.6363(3)
_cell_length_b                   10.3293(9)
_cell_length_c                   19.5855(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.632(5)
_cell_angle_gamma                90.00
_cell_volume                     936.06(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    10270
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9685
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
'SADABS reports: Ratio of minimum to maximum apparent transmission: 0.552476'
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10687
_diffrn_reflns_av_R_equivalents  0.1204
_diffrn_reflns_av_sigmaI/netI    0.0912
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.70
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2133
_reflns_number_gt                1257
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0671P)²+0.3109P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2133
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1242
_refine_ls_R_factor_gt           0.0660
_refine_ls_wR_factor_ref         0.1709
_refine_ls_wR_factor_gt          0.1464
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6239(5) 0.9334(2) 0.84940(13) 0.0311(6) Uani 1 1 d . . .
C2 C 0.4038(5) 0.8426(3) 0.84051(13) 0.0327(6) Uani 1 1 d . . .
C3 C 0.2850(6) 0.8091(3) 0.77632(15) 0.0410(7) Uani 1 1 d . . .
H3 H 0.1378 0.7451 0.7720 0.049 Uiso 1 1 calc R . .
C4 C 0.3799(6) 0.8686(3) 0.71806(15) 0.0442(8) Uani 1 1 d . . .
C5 C 0.5912(6) 0.9629(3) 0.72632(14) 0.0449(8) Uani 1 1 d . . .
H5 H 0.6541 1.0066 0.6873 0.054 Uiso 1 1 calc R . .
C6 C 0.7129(6) 0.9947(3) 0.79072(14) 0.0390(7) Uani 1 1 d . . .
H6 H 0.8590 1.0592 0.7950 0.047 Uiso 1 1 calc R . .
C7 C 0.7723(5) 0.9654(2) 0.91652(13) 0.0313(6) Uani 1 1 d . . .
C8 C 0.3864(6) 0.6839(2) 0.92732(15) 0.0359(6) Uani 1 1 d . . .
C9 C 0.2367(6) 0.6550(3) 0.99097(15) 0.0424(7) Uani 1 1 d . . .
H9A H 0.3056 0.5719 1.0099 0.064 Uiso 1 1 calc R . .
H9B H 0.0277 0.6504 0.9801 0.064 Uiso 1 1 calc R . .
H9C H 0.2788 0.7237 1.0247 0.064 Uiso 1 1 calc R . .
C10 C 0.2457(8) 0.8315(4) 0.64851(15) 0.0603(10) Uani 1 1 d . . .
H10A H 0.3690 0.8620 0.6130 0.090 Uiso 1 1 calc R . .
H10B H 0.0542 0.8714 0.6417 0.090 Uiso 1 1 calc R . .
H10C H 0.2269 0.7372 0.6457 0.090 Uiso 1 1 calc R . .
O1 O 0.9530(4) 1.05832(18) 0.91760(10) 0.0411(5) Uani 1 1 d . . .
H1 H 1.0488 1.0592 0.9555 0.062 Uiso 1 1 calc R . .
O2 O 0.7204(4) 0.90000(17) 0.96920(9) 0.0361(5) Uani 1 1 d . . .
O3 O 0.2703(4) 0.79215(17) 0.89704(9) 0.0353(5) Uani 1 1 d . . .
O4 O 0.5805(4) 0.62434(18) 0.90396(10) 0.0450(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0296(13) 0.0292(13) 0.0349(15) -0.0002(11) 0.0054(10) 0.0066(11)
C2 0.0320(13) 0.0292(14) 0.0369(15) 0.0012(11) 0.0030(11) 0.0091(11)
C3 0.0379(16) 0.0343(16) 0.0496(18) -0.0053(13) -0.0053(13) 0.0114(12)
C4 0.0440(17) 0.0460(18) 0.0422(17) -0.0049(14) -0.0012(13) 0.0237(14)
C5 0.0444(17) 0.0552(19) 0.0364(17) 0.0090(14) 0.0118(13) 0.0221(15)
C6 0.0352(15) 0.0408(17) 0.0418(18) 0.0018(13) 0.0085(12) 0.0046(12)
C7 0.0307(13) 0.0239(13) 0.0405(16) -0.0003(12) 0.0117(11) 0.0040(11)
C8 0.0343(14) 0.0248(14) 0.0469(17) -0.0032(12) -0.0119(12) 0.0017(12)
C9 0.0349(15) 0.0366(16) 0.0550(19) 0.0111(14) -0.0029(13) -0.0015(12)
C10 0.079(2) 0.062(2) 0.0381(18) -0.0093(16) -0.0093(16) 0.0338(19)
O1 0.0478(12) 0.0315(10) 0.0435(12) 0.0026(9) 0.0007(9) -0.0088(9)
O2 0.0428(11) 0.0331(10) 0.0331(11) -0.0005(8) 0.0087(8) -0.0040(8)
O3 0.0293(10) 0.0296(10) 0.0472(11) 0.0075(8) 0.0024(8) 0.0027(7)
O4 0.0504(13) 0.0335(11) 0.0498(13) -0.0066(9) -0.0063(10) 0.0122(10)

_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
C1 C2 1.388(4) . ?
C1 C6 1.397(4) . ?
C1 C7 1.482(4) . ?
C2 C3 1.384(4) . ?
C2 O3 1.403(3) . ?
C3 C4 1.392(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(4) . ?
C4 C10 1.511(4) . ?
C5 C6 1.388(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O2 1.269(3) . ?
C7 O1 1.273(3) . ?
C8 O4 1.204(3) . ?
C8 O3 1.360(3) . ?
C8 C9 1.495(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O1 H1 0.8400 . ?

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
C2 C1 C6 117.1(2) . . ?
C2 C1 C7 123.9(2) . . ?
C6 C1 C7 118.9(2) . . ?
C3 C2 C1 122.0(3) . . ?
C3 C2 O3 117.0(2) . . ?
C1 C2 O3 120.6(2) . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 118.3(3) . . ?
C5 C4 C10 122.2(3) . . ?
C3 C4 C10 119.6(3) . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 121.1(3) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
O2 C7 O1 123.1(2) . . ?
O2 C7 C1 120.1(2) . . ?
O1 C7 C1 116.8(2) . . ?
O4 C8 O3 122.6(3) . . ?
O4 C8 C9 127.7(3) . . ?
O3 C8 C9 109.6(2) . . ?
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 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 O1 H1 109.5 . . ?
C8 O3 C2 117.8(2) . . ?

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 H1 O2 0.84 1.82 2.640(3) 166.2 3_777

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.066

data_shelxl2
_database_code_depnum_ccdc_archive 'CCDC 643151'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'2-acetyloxy-5-bromobenzoic acid'
;
_chemical_name_common            "'2-acetyloxy-5-bromobenzoic acid'"
_chemical_melting_point          160
_chemical_formula_moiety         'C9 H7 Br O4'
_chemical_formula_sum            'C9 H7 Br O4'
_chemical_formula_weight         259.06

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  -P2yn

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

_cell_length_a                   10.3912(4)
_cell_length_b                   4.72650(10)
_cell_length_c                   19.5116(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.383(2)
_cell_angle_gamma                90.00
_cell_volume                     952.35(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2366
_cell_measurement_theta_min      1.02
_cell_measurement_theta_max      27.88

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.807
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    4.300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1665
_exptl_absorpt_correction_T_max  0.7248
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10114
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.53
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2171
_reflns_number_gt                1619
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0242P)²+1.1431P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2171
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0757
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.89296(3) 0.24254(7) 0.089926(16) 0.02812(11) Uani 1 1 d . . .
O1 O 1.50444(18) 0.2920(4) 0.06212(10) 0.0194(4) Uani 1 1 d . . .
H1 H 1.5522 0.1803 0.0430 0.029 Uiso 1 1 calc R . .
O2 O 1.34713(18) 0.0582(4) -0.00210(10) 0.0227(5) Uani 1 1 d . . .
O3 O 1.43271(18) 0.7316(4) 0.13639(10) 0.0210(4) Uani 1 1 d . . .
O4 O 1.5091(2) 0.4299(5) 0.22034(11) 0.0314(5) Uani 1 1 d . . .
C1 C 1.2859(3) 0.3749(6) 0.08204(14) 0.0171(6) Uani 1 1 d . . .
C2 C 1.3122(3) 0.5953(6) 0.12949(14) 0.0197(6) Uani 1 1 d . . .
C7 C 1.3829(3) 0.2294(6) 0.04338(13) 0.0173(5) Uani 1 1 d . . .
C4 C 1.0923(3) 0.5974(6) 0.15590(15) 0.0249(7) Uani 1 1 d . . .
H4 H 1.0270 0.6693 0.1815 0.030 Uiso 1 1 calc R . .
C3 C 1.2173(3) 0.7028(6) 0.16649(16) 0.0243(7) Uani 1 1 d . . .
H3 H 1.2379 0.8492 0.1993 0.029 Uiso 1 1 calc R . .
C5 C 1.0638(3) 0.3863(6) 0.10748(15) 0.0204(6) Uani 1 1 d . . .
C6 C 1.1590(3) 0.2751(6) 0.07096(14) 0.0177(6) Uani 1 1 d . . .
H6 H 1.1376 0.1296 0.0381 0.021 Uiso 1 1 calc R . .
C8 C 1.5276(3) 0.6261(6) 0.18358(15) 0.0207(6) Uani 1 1 d . . .
C9 C 1.6505(3) 0.7853(6) 0.18047(17) 0.0279(7) Uani 1 1 d . . .
H9A H 1.7110 0.7405 0.2212 0.042 Uiso 1 1 calc R . .
H9B H 1.6324 0.9889 0.1794 0.042 Uiso 1 1 calc R . .
H9C H 1.6890 0.7314 0.1387 0.042 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.01575(16) 0.03653(19) 0.03300(19) -0.00426(15) 0.00680(12) -0.00146(14)
O1 0.0152(10) 0.0237(11) 0.0197(10) -0.0023(8) 0.0031(8) -0.0049(8)
O2 0.0161(10) 0.0344(12) 0.0175(11) -0.0086(9) 0.0017(8) -0.0040(9)
O3 0.0206(10) 0.0169(10) 0.0231(10) 0.0036(9) -0.0079(8) -0.0039(8)
O4 0.0343(13) 0.0367(13) 0.0222(12) 0.0117(10) -0.0015(10) -0.0018(10)
C1 0.0195(15) 0.0181(13) 0.0136(14) 0.0029(11) 0.0014(11) 0.0000(11)
C2 0.0186(15) 0.0211(15) 0.0183(15) 0.0034(12) -0.0029(12) -0.0011(12)
C7 0.0182(13) 0.0203(14) 0.0135(13) 0.0044(12) 0.0021(10) -0.0033(12)
C4 0.0279(17) 0.0247(16) 0.0226(17) -0.0030(13) 0.0057(13) 0.0028(13)
C3 0.0303(17) 0.0198(15) 0.0213(16) -0.0040(12) -0.0031(13) 0.0037(12)
C5 0.0162(14) 0.0243(15) 0.0210(16) 0.0011(12) 0.0028(12) -0.0018(12)
C6 0.0170(13) 0.0187(14) 0.0177(14) -0.0022(12) 0.0030(11) -0.0014(12)
C8 0.0248(16) 0.0204(14) 0.0158(15) -0.0056(12) -0.0028(12) 0.0024(12)
C9 0.0255(16) 0.0262(16) 0.0296(17) -0.0004(14) -0.0079(13) -0.0027(13)

_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
Br1 C5 1.896(3) . ?
O1 C7 1.309(3) . ?
O1 H1 0.8400 . ?
O2 C7 1.228(3) . ?
O3 C8 1.366(3) . ?
O3 C2 1.401(3) . ?
O4 C8 1.201(4) . ?
C1 C2 1.401(4) . ?
C1 C6 1.394(4) . ?
C1 C7 1.492(4) . ?
C2 C3 1.382(4) . ?
C4 C5 1.383(4) . ?
C4 C3 1.385(4) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C5 C6 1.385(4) . ?
C6 H6 0.9500 . ?
C8 C9 1.490(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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
C7 O1 H1 109.5 . . ?
C8 O3 C2 117.8(2) . . ?
C2 C1 C6 117.8(3) . . ?
C2 C1 C7 125.7(3) . . ?
C6 C1 C7 116.5(2) . . ?
C1 C2 C3 121.4(3) . . ?
C1 C2 O3 120.8(2) . . ?
C3 C2 O3 117.6(3) . . ?
O2 C7 O1 123.8(2) . . ?
O2 C7 C1 120.1(2) . . ?
O1 C7 C1 116.1(2) . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 Br1 120.4(2) . . ?
C6 C5 Br1 118.6(2) . . ?
C5 C6 C1 120.6(3) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
O4 C8 O3 122.2(3) . . ?
O4 C8 C9 127.5(3) . . ?
O3 C8 C9 110.2(2) . . ?
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_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 H1 O2 0.84 1.79 2.625(3) 179.6 3_855

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.090

data_shelxl3
_database_code_depnum_ccdc_archive 'CCDC 643152'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'2-acetyloxy-5-chlorobenzoic acid'
;
_chemical_name_common            "'2-acetyloxy-5-chlorobenzoic acid'"
_chemical_melting_point          147
_chemical_formula_moiety         'C9 H7 Cl O4'
_chemical_formula_sum            'C9 H7 Cl O4'
_chemical_formula_weight         214.60

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  -P2yn

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

_cell_length_a                   10.1217(4)
_cell_length_b                   4.73590(10)
_cell_length_c                   19.4447(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.219(2)
_cell_angle_gamma                90.00
_cell_volume                     926.60(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7186
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7954
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12125
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2111
_reflns_number_gt                1608
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0422P)²+0.3205P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2111
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.89012(4) 0.24922(10) 0.08962(3) 0.03417(16) Uani 1 1 d . . .
O1 O 1.50405(11) 0.2919(2) 0.06227(6) 0.0240(3) Uani 1 1 d . . .
H1 H 1.5531 0.1840 0.0420 0.036 Uiso 1 1 calc R . .
O2 O 1.34381(12) 0.0617(3) -0.00313(6) 0.0276(3) Uani 1 1 d . . .
O3 O 1.42747(12) 0.7354(2) 0.13518(6) 0.0243(3) Uani 1 1 d . . .
O4 O 1.50466(13) 0.4410(3) 0.22098(6) 0.0363(3) Uani 1 1 d . . .
C1 C 1.27844(17) 0.3778(3) 0.08062(8) 0.0208(4) Uani 1 1 d . . .
C2 C 1.30452(17) 0.5978(3) 0.12809(8) 0.0225(4) Uani 1 1 d . . .
C7 C 1.37923(17) 0.2334(3) 0.04250(8) 0.0209(4) Uani 1 1 d . . .
C4 C 1.07763(19) 0.5956(4) 0.15396(9) 0.0288(4) Uani 1 1 d . . .
H4 H 1.0097 0.6659 0.1794 0.035 Uiso 1 1 calc R . .
C3 C 1.20569(19) 0.7033(4) 0.16482(9) 0.0276(4) Uani 1 1 d . . .
H3 H 1.2256 0.8501 0.1976 0.033 Uiso 1 1 calc R . .
C5 C 1.05048(17) 0.3837(4) 0.10529(9) 0.0248(4) Uani 1 1 d . . .
C6 C 1.14872(18) 0.2738(3) 0.06894(9) 0.0230(4) Uani 1 1 d . . .
H6 H 1.1281 0.1278 0.0360 0.028 Uiso 1 1 calc R . .
C8 C 1.52437(18) 0.6337(4) 0.18347(9) 0.0247(4) Uani 1 1 d . . .
C9 C 1.65038(19) 0.7914(4) 0.18035(10) 0.0317(4) Uani 1 1 d . . .
H9A H 1.7132 0.7420 0.2205 0.047 Uiso 1 1 calc R . .
H9B H 1.6325 0.9947 0.1807 0.047 Uiso 1 1 calc R . .
H9C H 1.6887 0.7415 0.1378 0.047 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0198(3) 0.0406(3) 0.0428(3) -0.0079(2) 0.00690(19) -0.00353(19)
O1 0.0178(6) 0.0295(7) 0.0247(7) -0.0023(5) 0.0031(5) -0.0044(5)
O2 0.0225(7) 0.0365(7) 0.0236(6) -0.0077(5) 0.0021(5) -0.0044(5)
O3 0.0241(7) 0.0196(6) 0.0274(7) 0.0018(5) -0.0055(5) -0.0030(5)
O4 0.0364(8) 0.0424(8) 0.0289(7) 0.0113(6) -0.0011(6) -0.0014(6)
C1 0.0224(9) 0.0209(8) 0.0189(8) 0.0032(7) 0.0010(6) -0.0016(7)
C2 0.0228(9) 0.0204(9) 0.0230(9) 0.0033(7) -0.0033(7) -0.0032(7)
C7 0.0209(9) 0.0239(9) 0.0176(8) 0.0036(7) 0.0006(7) -0.0042(7)
C4 0.0302(10) 0.0291(10) 0.0276(10) -0.0022(7) 0.0053(8) 0.0040(8)
C3 0.0314(11) 0.0223(9) 0.0282(10) -0.0042(7) -0.0008(8) 0.0018(8)
C5 0.0199(9) 0.0277(9) 0.0267(9) -0.0001(7) 0.0024(7) -0.0016(7)
C6 0.0241(9) 0.0237(9) 0.0213(9) -0.0027(7) 0.0029(7) -0.0031(7)
C8 0.0294(10) 0.0230(9) 0.0207(9) -0.0030(7) -0.0024(7) 0.0033(7)
C9 0.0291(10) 0.0288(10) 0.0344(11) 0.0009(8) -0.0089(8) -0.0023(8)

_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
Cl1 C5 1.7394(17) . ?
O1 C7 1.3097(19) . ?
O1 H1 0.8400 . ?
O2 C7 1.2281(19) . ?
O3 C8 1.370(2) . ?
O3 C2 1.398(2) . ?
O4 C8 1.198(2) . ?
C1 C6 1.398(2) . ?
C1 C2 1.398(2) . ?
C1 C7 1.490(2) . ?
C2 C3 1.384(3) . ?
C4 C5 1.386(2) . ?
C4 C3 1.388(3) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C5 C6 1.383(2) . ?
C6 H6 0.9500 . ?
C8 C9 1.485(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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
C7 O1 H1 109.5 . . ?
C8 O3 C2 117.85(13) . . ?
C6 C1 C2 118.47(16) . . ?
C6 C1 C7 116.05(15) . . ?
C2 C1 C7 125.44(15) . . ?
C3 C2 C1 120.97(16) . . ?
C3 C2 O3 117.76(15) . . ?
C1 C2 O3 121.00(15) . . ?
O2 C7 O1 123.29(16) . . ?
O2 C7 C1 120.07(15) . . ?
O1 C7 C1 116.59(14) . . ?
C5 C4 C3 118.88(17) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C2 C3 C4 120.26(16) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C6 C5 C4 121.40(16) . . ?
C6 C5 Cl1 118.81(13) . . ?
C4 C5 Cl1 119.79(14) . . ?
C5 C6 C1 119.96(16) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O4 C8 O3 122.07(17) . . ?
O4 C8 C9 127.46(16) . . ?
O3 C8 C9 110.46(15) . . ?
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_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 H1 O2 0.84 1.78 2.6233(17) 176.3 3_855

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.055

data_shelxl4
_database_code_depnum_ccdc_archive 'CCDC 643153'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'2-acetyloxy-5-fluorobenzoic acid'
;
_chemical_name_common            "'2-acetyloxy-5-fluorobenzoic acid'"
_chemical_melting_point          131
_chemical_formula_moiety         'C9 H7 F O4'
_chemical_formula_sum            'C9 H7 F O4'
_chemical_formula_weight         198.15

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  -P2yn

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

_cell_length_a                   9.7655(5)
_cell_length_b                   4.8919(2)
_cell_length_c                   18.3338(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.739(3)
_cell_angle_gamma                90.00
_cell_volume                     847.02(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5271
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9537
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
'SADABS reports: Ratio of minimum to maximum apparent transmission: 0.715428'
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7983
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1933
_reflns_number_gt                1371
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0622P)²+0.3309P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1933
_refine_ls_number_parameters     132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.981
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H1 H 0.406(3) 1.093(6) 0.4540(19) 0.073(9) Uiso 1 1 d . . .
C1 C 0.48881(18) 0.7282(4) 0.32746(10) 0.0187(4) Uani 1 1 d . . .
C2 C 0.57180(19) 0.5081(4) 0.31555(10) 0.0198(4) Uani 1 1 d . . .
C3 C 0.5756(2) 0.4307(4) 0.24341(10) 0.0222(4) Uani 1 1 d . . .
H3 H 0.6336 0.2819 0.2366 0.027 Uiso 1 1 calc R . .
C4 C 0.4954(2) 0.5695(4) 0.18109(10) 0.0253(4) Uani 1 1 d . . .
H4 H 0.4977 0.5184 0.1314 0.030 Uiso 1 1 calc R . .
C5 C 0.4123(2) 0.7830(4) 0.19330(10) 0.0234(4) Uani 1 1 d . . .
C6 C 0.40687(19) 0.8651(4) 0.26438(10) 0.0213(4) Uani 1 1 d . . .
H6 H 0.3480 1.0134 0.2705 0.026 Uiso 1 1 calc R . .
C7 C 0.49036(18) 0.8303(4) 0.40391(10) 0.0194(4) Uani 1 1 d . . .
C8 C 0.77731(19) 0.4262(4) 0.41320(10) 0.0201(4) Uani 1 1 d . . .
C9 C 0.8331(2) 0.2470(4) 0.47958(11) 0.0247(4) Uani 1 1 d . . .
H9A H 0.9334 0.2884 0.5014 0.037 Uiso 1 1 calc R . .
H9B H 0.8231 0.0552 0.4637 0.037 Uiso 1 1 calc R . .
H9C H 0.7797 0.2793 0.5174 0.037 Uiso 1 1 calc R . .
O1 O 0.39019(14) 1.0106(3) 0.40388(8) 0.0264(3) Uani 1 1 d . . .
O2 O 0.57810(14) 0.7578(3) 0.46135(7) 0.0239(3) Uani 1 1 d . . .
O3 O 0.64446(13) 0.3446(3) 0.37531(7) 0.0207(3) Uani 1 1 d . . .
O4 O 0.83558(13) 0.6168(3) 0.39270(7) 0.0262(3) Uani 1 1 d . . .
F F 0.33388(12) 0.9229(2) 0.13308(6) 0.0321(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0200(9) 0.0208(9) 0.0165(9) -0.0020(7) 0.0067(7) -0.0057(7)
C2 0.0217(9) 0.0204(9) 0.0172(9) -0.0002(7) 0.0047(7) -0.0040(7)
C3 0.0257(10) 0.0207(9) 0.0214(10) -0.0044(7) 0.0083(8) -0.0032(8)
C4 0.0344(11) 0.0260(10) 0.0175(9) -0.0050(7) 0.0102(8) -0.0084(8)
C5 0.0267(10) 0.0264(10) 0.0158(9) 0.0036(7) 0.0031(8) -0.0062(8)
C6 0.0213(9) 0.0204(9) 0.0221(9) 0.0018(7) 0.0054(7) -0.0011(7)
C7 0.0194(9) 0.0199(9) 0.0205(9) -0.0004(7) 0.0081(7) -0.0028(7)
C8 0.0215(9) 0.0211(9) 0.0188(9) -0.0053(7) 0.0070(7) -0.0021(7)
C9 0.0267(10) 0.0235(9) 0.0230(10) 0.0008(8) 0.0044(8) -0.0023(8)
O1 0.0258(7) 0.0324(8) 0.0215(7) -0.0055(6) 0.0065(6) 0.0061(6)
O2 0.0277(7) 0.0274(7) 0.0160(7) -0.0013(5) 0.0048(6) 0.0038(6)
O3 0.0220(6) 0.0193(6) 0.0197(6) 0.0009(5) 0.0032(5) -0.0008(5)
O4 0.0253(7) 0.0279(7) 0.0260(7) 0.0023(6) 0.0078(6) -0.0054(6)
F 0.0383(7) 0.0346(7) 0.0196(6) 0.0073(5) 0.0003(5) -0.0020(5)

_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
C1 C2 1.398(3) . ?
C1 C6 1.398(3) . ?
C1 C7 1.484(2) . ?
C2 C3 1.385(3) . ?
C2 O3 1.396(2) . ?
C3 C4 1.387(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9500 . ?
C5 F 1.357(2) . ?
C5 C6 1.377(3) . ?
C6 H6 0.9500 . ?
C7 O2 1.229(2) . ?
C7 O1 1.317(2) . ?
C8 O4 1.201(2) . ?
C8 O3 1.366(2) . ?
C8 C9 1.486(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O1 H1 0.98(3) . ?

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
C2 C1 C6 118.18(16) . . ?
C2 C1 C7 122.66(16) . . ?
C6 C1 C7 119.08(16) . . ?
C3 C2 O3 117.47(16) . . ?
C3 C2 C1 121.14(16) . . ?
O3 C2 C1 121.19(16) . . ?
C2 C3 C4 120.38(18) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 118.07(17) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
F C5 C4 118.96(17) . . ?
F C5 C6 118.25(17) . . ?
C4 C5 C6 122.78(17) . . ?
C5 C6 C1 119.43(17) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
O2 C7 O1 123.33(16) . . ?
O2 C7 C1 123.34(16) . . ?
O1 C7 C1 113.32(15) . . ?
O4 C8 O3 122.12(17) . . ?
O4 C8 C9 127.56(17) . . ?
O3 C8 C9 110.32(15) . . ?
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 . . ?
C7 O1 H1 109.7(18) . . ?
C8 O3 C2 117.35(14) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.062

data_shelxl5
_database_code_depnum_ccdc_archive 'CCDC 643154'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'2-acetyloxy-5-iodobenzoic acid'
;
_chemical_name_common            "'2-acetyloxy-5-iodobenzoic acid'"
_chemical_melting_point          170
_chemical_formula_moiety         'C9 H7 I O4'
_chemical_formula_sum            'C9 H7 I O4'
_chemical_formula_weight         306.05

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  -P2yn

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

_cell_length_a                   10.7838(5)
_cell_length_b                   4.7168(2)
_cell_length_c                   19.5502(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.630(2)
_cell_angle_gamma                90.00
_cell_volume                     987.77(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2344
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.058
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    3.227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6981
_exptl_absorpt_correction_T_max  0.9094
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8826
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.48
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2238
_reflns_number_gt                1894
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+5.0845P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2238
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0806
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.90014(2) 0.23980(7) 0.091686(15) 0.02708(13) Uani 1 1 d . . .
O1 O 1.5059(3) 0.2883(7) 0.06181(15) 0.0219(6) Uani 1 1 d . . .
H1 H 1.5500 0.1828 0.0398 0.033 Uiso 1 1 calc R . .
O2 O 1.3516(3) 0.0517(7) 0.00070(15) 0.0248(7) Uani 1 1 d . . .
O3 O 1.4413(3) 0.7268(6) 0.13838(15) 0.0218(6) Uani 1 1 d . . .
O4 O 1.5178(3) 0.4151(7) 0.21980(16) 0.0310(8) Uani 1 1 d . . .
C1 C 1.2969(4) 0.3733(9) 0.0853(2) 0.0196(8) Uani 1 1 d . . .
C2 C 1.3247(4) 0.5924(9) 0.1323(2) 0.0203(8) Uani 1 1 d . . .
C7 C 1.3879(4) 0.2265(9) 0.0453(2) 0.0201(8) Uani 1 1 d . . .
C4 C 1.1137(4) 0.6014(10) 0.1600(2) 0.0267(10) Uani 1 1 d . . .
H4 H 1.0523 0.6755 0.1862 0.032 Uiso 1 1 calc R . .
C3 C 1.2350(4) 0.7025(9) 0.1695(2) 0.0238(9) Uani 1 1 d . . .
H3 H 1.2566 0.8493 0.2019 0.029 Uiso 1 1 calc R . .
C5 C 1.0833(4) 0.3894(9) 0.1114(2) 0.0203(8) Uani 1 1 d . . .
C6 C 1.1740(4) 0.2735(9) 0.0748(2) 0.0205(8) Uani 1 1 d . . .
H6 H 1.1526 0.1259 0.0426 0.025 Uiso 1 1 calc R . .
C8 C 1.5346(4) 0.6141(10) 0.1839(2) 0.0229(9) Uani 1 1 d . . .
C9 C 1.6522(4) 0.7735(10) 0.1804(2) 0.0280(10) Uani 1 1 d . . .
H9A H 1.7139 0.7157 0.2186 0.042 Uiso 1 1 calc R . .
H9B H 1.6359 0.9771 0.1838 0.042 Uiso 1 1 calc R . .
H9C H 1.6845 0.7331 0.1366 0.042 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.01545(17) 0.0338(2) 0.03283(19) -0.00089(13) 0.00611(11) -0.00043(13)
O1 0.0139(14) 0.0288(17) 0.0233(15) -0.0031(12) 0.0037(11) -0.0061(13)
O2 0.0156(15) 0.0337(18) 0.0250(15) -0.0067(13) 0.0027(12) -0.0037(13)
O3 0.0210(15) 0.0182(15) 0.0243(15) 0.0022(12) -0.0050(11) -0.0017(13)
O4 0.0330(19) 0.0324(19) 0.0269(17) 0.0085(14) 0.0013(14) -0.0013(15)
C1 0.018(2) 0.024(2) 0.0171(19) 0.0034(16) 0.0024(15) 0.0013(17)
C2 0.016(2) 0.020(2) 0.025(2) 0.0032(16) 0.0003(16) -0.0023(16)
C7 0.018(2) 0.024(2) 0.0181(18) 0.0059(17) 0.0022(15) -0.0028(18)
C4 0.026(2) 0.029(2) 0.025(2) 0.0005(18) 0.0056(18) 0.005(2)
C3 0.024(2) 0.021(2) 0.025(2) -0.0038(17) -0.0026(17) 0.0066(18)
C5 0.015(2) 0.025(2) 0.021(2) 0.0042(16) 0.0032(15) 0.0008(17)
C6 0.019(2) 0.021(2) 0.0212(19) 0.0002(16) 0.0036(15) -0.0017(17)
C8 0.023(2) 0.022(2) 0.023(2) -0.0040(17) 0.0011(17) 0.0046(18)
C9 0.024(2) 0.023(2) 0.034(2) -0.0001(19) -0.0070(18) -0.0015(19)

_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
I1 C5 2.091(4) . ?
O1 C7 1.309(5) . ?
O1 H1 0.8400 . ?
O2 C7 1.231(5) . ?
O3 C8 1.371(5) . ?
O3 C2 1.401(5) . ?
O4 C8 1.198(5) . ?
C1 C2 1.392(6) . ?
C1 C6 1.399(6) . ?
C1 C7 1.493(6) . ?
C2 C3 1.377(6) . ?
C4 C3 1.384(6) . ?
C4 C5 1.393(6) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C5 C6 1.389(6) . ?
C6 H6 0.9500 . ?
C8 C9 1.482(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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
C7 O1 H1 109.5 . . ?
C8 O3 C2 117.6(3) . . ?
C2 C1 C6 118.3(4) . . ?
C2 C1 C7 125.8(4) . . ?
C6 C1 C7 115.8(4) . . ?
C3 C2 C1 121.1(4) . . ?
C3 C2 O3 117.6(4) . . ?
C1 C2 O3 121.0(4) . . ?
O2 C7 O1 123.0(4) . . ?
O2 C7 C1 120.5(4) . . ?
O1 C7 C1 116.5(4) . . ?
C3 C4 C5 118.9(4) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C2 C3 C4 120.7(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 I1 118.6(3) . . ?
C4 C5 I1 120.8(3) . . ?
C5 C6 C1 120.3(4) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O4 C8 O3 122.3(4) . . ?
O4 C8 C9 127.8(4) . . ?
O3 C8 C9 109.9(4) . . ?
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_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 H1 O2 0.84 1.78 2.619(4) 175.7 3_855

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.125

data_shelxl6
_database_code_depnum_ccdc_archive 'CCDC 643155'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'2-acetyloxy-5-methylbenzoic acid'
;
_chemical_name_common            "'2-acetyloxy-5-methylbenzoic acid'"
_chemical_melting_point          146
_chemical_formula_moiety         'C10 H10 O4'
_chemical_formula_sum            'C10 H10 O4'
_chemical_formula_weight         194.18

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  -P2yn

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

_cell_length_a                   10.1301(3)
_cell_length_b                   4.88310(10)
_cell_length_c                   18.9682(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.696(2)
_cell_angle_gamma                90.00
_cell_volume                     921.98(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2304
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9425
_exptl_absorpt_correction_T_max  0.9785
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
'SADABS reports: Ratio of minimum to maximum apparent transmission: 0.794711'
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10082
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.53
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2117
_reflns_number_gt                1616
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0574P)²+0.3231P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2117
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1070
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C10 C 0.35162(17) 0.8769(4) 0.14823(9) 0.0276(4) Uani 1 1 d . . .
H10A H 0.3683 0.7938 0.1037 0.041 Uiso 0.50 1 calc PR . .
H10B H 0.3754 1.0715 0.1490 0.041 Uiso 0.50 1 calc PR . .
H10C H 0.2563 0.8578 0.1509 0.041 Uiso 0.50 1 calc PR . .
H10D H 0.2984 1.0216 0.1654 0.041 Uiso 0.50 1 calc PR . .
H10E H 0.2913 0.7439 0.1200 0.041 Uiso 0.50 1 calc PR . .
H10F H 0.4104 0.9576 0.1182 0.041 Uiso 0.50 1 calc PR . .
C1 C 0.50954(15) 0.6887(3) 0.34108(8) 0.0196(3) Uani 1 1 d . . .
C2 C 0.59286(15) 0.4720(3) 0.32904(8) 0.0205(3) Uani 1 1 d . . .
C3 C 0.60038(16) 0.3903(3) 0.26004(9) 0.0242(4) Uani 1 1 d . . .
H3 H 0.6579 0.2439 0.2525 0.029 Uiso 1 1 calc R . .
C4 C 0.52352(16) 0.5231(3) 0.20200(9) 0.0245(4) Uani 1 1 d . . .
H4 H 0.5306 0.4691 0.1547 0.029 Uiso 1 1 calc R . .
C5 C 0.43593(16) 0.7346(3) 0.21153(8) 0.0225(4) Uani 1 1 d . . .
C6 C 0.43088(15) 0.8143(3) 0.28131(8) 0.0214(3) Uani 1 1 d . . .
H6 H 0.3721 0.9588 0.2887 0.026 Uiso 1 1 calc R . .
C7 C 0.50169(15) 0.8044(3) 0.41241(8) 0.0206(3) Uani 1 1 d . . .
C8 C 0.78777(15) 0.3985(3) 0.41726(8) 0.0211(3) Uani 1 1 d . . .
C9 C 0.84164(16) 0.2180(3) 0.47944(9) 0.0262(4) Uani 1 1 d . . .
H9A H 0.9334 0.2745 0.5003 0.039 Uiso 1 1 calc R . .
H9B H 0.8423 0.0276 0.4631 0.039 Uiso 1 1 calc R . .
H9C H 0.7846 0.2332 0.5157 0.039 Uiso 1 1 calc R . .
O2 O 0.41197(11) 0.9698(3) 0.41903(6) 0.0288(3) Uani 1 1 d . . .
O1 O 0.59411(11) 0.7281(2) 0.46650(6) 0.0251(3) Uani 1 1 d . . .
H1 H 0.5867 0.8200 0.5030 0.038 Uiso 1 1 calc R . .
O3 O 0.66178(10) 0.3148(2) 0.38617(6) 0.0223(3) Uani 1 1 d . . .
O4 O 0.84315(11) 0.5894(2) 0.39569(6) 0.0276(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C10 0.0270(9) 0.0317(9) 0.0225(8) 0.0010(7) 0.0010(6) -0.0029(7)
C1 0.0175(8) 0.0208(8) 0.0210(8) -0.0010(6) 0.0049(6) -0.0032(6)
C2 0.0183(7) 0.0181(8) 0.0245(8) 0.0007(6) 0.0023(6) -0.0030(6)
C3 0.0239(8) 0.0211(8) 0.0285(9) -0.0055(7) 0.0071(6) -0.0021(6)
C4 0.0280(8) 0.0244(8) 0.0220(8) -0.0052(7) 0.0067(6) -0.0052(7)
C5 0.0212(8) 0.0243(8) 0.0216(8) -0.0011(6) 0.0030(6) -0.0060(6)
C6 0.0192(8) 0.0219(8) 0.0235(8) -0.0003(6) 0.0046(6) -0.0009(6)
C7 0.0180(8) 0.0232(8) 0.0211(8) 0.0017(6) 0.0050(6) -0.0006(6)
C8 0.0190(8) 0.0192(8) 0.0257(8) -0.0062(6) 0.0056(6) -0.0004(6)
C9 0.0241(9) 0.0233(8) 0.0296(9) -0.0013(7) 0.0006(7) 0.0000(7)
O2 0.0235(6) 0.0378(7) 0.0249(6) -0.0036(5) 0.0044(5) 0.0083(5)
O1 0.0250(6) 0.0316(7) 0.0182(6) -0.0007(5) 0.0028(4) 0.0058(5)
O3 0.0200(6) 0.0180(6) 0.0275(6) 0.0018(5) 0.0007(4) -0.0012(4)
O4 0.0236(6) 0.0265(6) 0.0336(7) -0.0004(5) 0.0075(5) -0.0056(5)

_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
C10 C5 1.508(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 H10D 0.9800 . ?
C10 H10E 0.9800 . ?
C10 H10F 0.9800 . ?
C1 C2 1.399(2) . ?
C1 C6 1.400(2) . ?
C1 C7 1.482(2) . ?
C2 C3 1.384(2) . ?
C2 O3 1.4037(19) . ?
C3 C4 1.386(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(2) . ?
C6 H6 0.9500 . ?
C7 O2 1.2396(18) . ?
C7 O1 1.3081(18) . ?
C8 O4 1.1985(19) . ?
C8 O3 1.3654(18) . ?
C8 C9 1.492(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O1 H1 0.8400 . ?

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
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C10 H10D 109.5 . . ?
H10A C10 H10D 141.1 . . ?
H10B C10 H10D 56.3 . . ?
H10C C10 H10D 56.3 . . ?
C5 C10 H10E 109.5 . . ?
H10A C10 H10E 56.3 . . ?
H10B C10 H10E 141.1 . . ?
H10C C10 H10E 56.3 . . ?
H10D C10 H10E 109.5 . . ?
C5 C10 H10F 109.5 . . ?
H10A C10 H10F 56.3 . . ?
H10B C10 H10F 56.3 . . ?
H10C C10 H10F 141.1 . . ?
H10D C10 H10F 109.5 . . ?
H10E C10 H10F 109.5 . . ?
C2 C1 C6 117.99(14) . . ?
C2 C1 C7 125.01(14) . . ?
C6 C1 C7 116.95(14) . . ?
C3 C2 C1 120.89(15) . . ?
C3 C2 O3 117.76(14) . . ?
C1 C2 O3 121.10(13) . . ?
C2 C3 C4 119.66(15) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 121.38(14) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 117.87(15) . . ?
C6 C5 C10 120.91(15) . . ?
C4 C5 C10 121.20(14) . . ?
C5 C6 C1 122.16(15) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 H6 118.9 . . ?
O2 C7 O1 122.53(14) . . ?
O2 C7 C1 120.36(14) . . ?
O1 C7 C1 117.10(13) . . ?
O4 C8 O3 123.00(15) . . ?
O4 C8 C9 127.13(15) . . ?
O3 C8 C9 109.87(13) . . ?
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 . . ?
C7 O1 H1 109.5 . . ?
C8 O3 C2 117.44(12) . . ?

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 H1 O2 0.84 1.80 2.6354(16) 174.0 3_676

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.059

data_shelxl7
_database_code_depnum_ccdc_archive 'CCDC 643156'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'2-acetyloxy-5-nitrobenzoic acid'
;
_chemical_name_common            "'2-acetyloxy-5-nitrobenzoic acid'"
_chemical_melting_point          162
_chemical_formula_moiety         'C9 H7 N O6'
_chemical_formula_sum            'C9 H7 N O6'
_chemical_formula_weight         225.16

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn '

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

_cell_length_a                   9.9166(3)
_cell_length_b                   5.04440(10)
_cell_length_c                   18.6808(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.6860(10)
_cell_angle_gamma                90.00
_cell_volume                     921.15(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4600
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Rod
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9333
_exptl_absorpt_correction_T_max  0.9779
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
'SADABS results: Ratio of minimum to maximum apparent transmission: 0.836455'
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8929
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.61
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2102
_reflns_number_gt                1804
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0496P)²+0.3793P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2102
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.36435(10) 0.7492(2) 0.08354(5) 0.0214(2) Uani 1 1 d . . .
O5 O 0.28836(11) 1.0388(2) 0.15267(5) 0.0289(3) Uani 1 1 d . . .
N1 N 0.35863(11) 0.8454(2) 0.14331(6) 0.0165(2) Uani 1 1 d . . .
C1 C 0.51004(12) 0.7049(2) 0.33681(6) 0.0138(3) Uani 1 1 d . . .
C2 C 0.59018(12) 0.4836(2) 0.32678(6) 0.0143(3) Uani 1 1 d . . .
C3 C 0.59775(13) 0.3878(3) 0.25788(7) 0.0171(3) Uani 1 1 d . . .
H3 H 0.6548 0.2405 0.2524 0.020 Uiso 1 1 calc R . .
C4 C 0.52233(13) 0.5064(3) 0.19712(7) 0.0164(3) Uani 1 1 d . . .
H4 H 0.5265 0.4421 0.1498 0.020 Uiso 1 1 calc R . .
C5 C 0.44076(12) 0.7210(3) 0.20732(6) 0.0142(3) Uani 1 1 d . . .
C6 C 0.43315(12) 0.8228(3) 0.27534(6) 0.0146(3) Uani 1 1 d . . .
H6 H 0.3764 0.9711 0.2802 0.017 Uiso 1 1 calc R . .
C7 C 0.50266(12) 0.8242(3) 0.40944(6) 0.0144(3) Uani 1 1 d . . .
C8 C 0.78697(12) 0.4084(3) 0.41542(7) 0.0153(3) Uani 1 1 d . . .
C9 C 0.83853(14) 0.2353(3) 0.47864(7) 0.0185(3) Uani 1 1 d . . .
H9A H 0.9341 0.2795 0.4975 0.028 Uiso 1 1 calc R . .
H9B H 0.8322 0.0493 0.4633 0.028 Uiso 1 1 calc R . .
H9C H 0.7832 0.2630 0.5168 0.028 Uiso 1 1 calc R . .
O1 O 0.41227(9) 1.00710(19) 0.40919(5) 0.0206(2) Uani 1 1 d . . .
H1 H 0.4212 1.0773 0.4505 0.031 Uiso 1 1 calc R . .
O2 O 0.58303(10) 0.7491(2) 0.46457(5) 0.0228(2) Uani 1 1 d . . .
O3 O 0.65588(9) 0.33661(18) 0.38549(5) 0.0162(2) Uani 1 1 d . . .
O4 O 0.84551(10) 0.5850(2) 0.39047(5) 0.0247(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O6 0.0257(5) 0.0256(5) 0.0125(4) -0.0032(4) 0.0019(4) 0.0001(4)
O5 0.0322(6) 0.0326(6) 0.0213(5) -0.0002(4) 0.0031(4) 0.0186(5)
N1 0.0151(5) 0.0195(5) 0.0148(5) -0.0016(4) 0.0020(4) 0.0011(4)
C1 0.0132(6) 0.0152(6) 0.0137(6) -0.0020(4) 0.0039(4) -0.0036(5)
C2 0.0137(6) 0.0134(6) 0.0155(6) 0.0013(4) 0.0014(4) -0.0033(5)
C3 0.0179(6) 0.0141(6) 0.0196(6) -0.0016(5) 0.0044(5) 0.0022(5)
C4 0.0185(6) 0.0163(6) 0.0149(6) -0.0032(5) 0.0044(5) -0.0006(5)
C5 0.0130(6) 0.0162(6) 0.0131(6) -0.0005(4) 0.0016(4) -0.0013(5)
C6 0.0138(6) 0.0147(6) 0.0158(6) -0.0017(5) 0.0040(5) -0.0002(5)
C7 0.0138(6) 0.0157(6) 0.0140(6) -0.0005(5) 0.0037(4) -0.0035(5)
C8 0.0151(6) 0.0154(6) 0.0157(6) -0.0011(5) 0.0036(5) -0.0005(5)
C9 0.0198(6) 0.0182(6) 0.0170(6) 0.0029(5) 0.0013(5) -0.0024(5)
O1 0.0210(5) 0.0231(5) 0.0188(5) -0.0074(4) 0.0062(4) 0.0008(4)
O2 0.0251(5) 0.0298(6) 0.0127(4) -0.0015(4) 0.0006(4) 0.0008(4)
O3 0.0152(5) 0.0149(4) 0.0176(4) 0.0034(3) 0.0002(3) -0.0023(3)
O4 0.0200(5) 0.0257(5) 0.0275(5) 0.0109(4) 0.0015(4) -0.0070(4)

_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
O6 N1 1.2276(14) . ?
O5 N1 1.2285(15) . ?
N1 C5 1.4693(16) . ?
C1 C6 1.3997(18) . ?
C1 C2 1.4009(18) . ?
C1 C7 1.4973(16) . ?
C2 C3 1.3886(17) . ?
C2 O3 1.3917(15) . ?
C3 C4 1.3855(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3835(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3844(17) . ?
C6 H6 0.9500 . ?
C7 O2 1.2504(15) . ?
C7 O1 1.2857(16) . ?
C8 O4 1.1997(16) . ?
C8 O3 1.3745(15) . ?
C8 C9 1.4884(17) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O1 H1 0.8400 . ?

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
O6 N1 O5 123.88(11) . . ?
O6 N1 C5 117.86(10) . . ?
O5 N1 C5 118.26(10) . . ?
C6 C1 C2 118.15(11) . . ?
C6 C1 C7 118.01(11) . . ?
C2 C1 C7 123.83(11) . . ?
C3 C2 O3 116.99(11) . . ?
C3 C2 C1 121.44(11) . . ?
O3 C2 C1 121.34(11) . . ?
C4 C3 C2 120.21(12) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 118.19(11) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C4 C5 C6 122.69(12) . . ?
C4 C5 N1 118.62(11) . . ?
C6 C5 N1 118.69(11) . . ?
C5 C6 C1 119.28(12) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
O2 C7 O1 124.61(11) . . ?
O2 C7 C1 120.19(11) . . ?
O1 C7 C1 115.18(11) . . ?
O4 C8 O3 121.60(11) . . ?
O4 C8 C9 128.31(12) . . ?
O3 C8 C9 110.08(10) . . ?
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 . . ?
C7 O1 H1 109.5 . . ?
C8 O3 C2 117.75(10) . . ?

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 H1 O2 0.84 1.82 2.6532(13) 171.8 3_676

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.055


