Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2007

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data_s94
_database_code_depnum_ccdc_archive 'CCDC 292209'

_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C7 H9 N O6'
_chemical_formula_weight 203.15

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'
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)/c

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

_cell_length_a 3.65790(10)
_cell_length_b 11.0577(4)
_cell_length_c 21.5478(10)
_cell_angle_alpha 90.00
_cell_angle_beta 93.0200(10)
_cell_angle_gamma 90.00
_cell_volume 870.35(6)
_cell_formula_units_Z 4
_cell_measurement_temperature 120(2)
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?

_exptl_crystal_description Plate
_exptl_crystal_colour Colourless
_exptl_crystal_size_max 0.34
_exptl_crystal_size_mid 0.32
_exptl_crystal_size_min 0.12
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.550
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 424
_exptl_absorpt_coefficient_mu 0.138
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_min 0.9545
_exptl_absorpt_correction_T_max 0.9836
_exptl_absorpt_process_details 'SORTAV Blessing (1997)'
_exptl_special_details
;
PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
the entire data set is used to refine the cell, which is indexed from all
observed reflections in a 10 degree phi range.
;
_diffrn_ambient_temperature 120(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Nonius KappaCCD Area Detector'
_diffrn_measurement_method '\f and \w scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 9977
_diffrn_reflns_av_R_equivalents 0.0812
_diffrn_reflns_av_sigmaI/netI 0.0744
_diffrn_reflns_limit_h_min -4
_diffrn_reflns_limit_h_max 4
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -27
_diffrn_reflns_limit_l_max 27
_diffrn_reflns_theta_min 3.39
_diffrn_reflns_theta_max 27.48
_reflns_number_total 1969
_reflns_number_gt 1252
_reflns_threshold_expression >2sigma(I)

_computing_data_collection ' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)'
_computing_molecular_graphics 'PLATON (Spek, 1990)'
_computing_publication_material ?

_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0532P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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 1969
_refine_ls_number_parameters 145
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0929
_refine_ls_R_factor_gt 0.0466
_refine_ls_wR_factor_ref 0.1119
_refine_ls_wR_factor_gt 0.0927
_refine_ls_goodness_of_fit_ref 1.013
_refine_ls_restrained_S_all 1.013
_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 0.7737(5) 0.25587(16) 0.47775(8) 0.0192(4) Uani 1 1 d . . .
C2 C 0.6046(5) 0.30963(16) 0.41926(9) 0.0184(4) Uani 1 1 d . . .
C3 C 0.5900(5) 0.43341(16) 0.40839(9) 0.0208(4) Uani 1 1 d . . .
H3 H 0.6840 0.4889 0.4389 0.025 Uiso 1 1 calc R . .
C4 C 0.4354(5) 0.47416(17) 0.35212(9) 0.0240(5) Uani 1 1 d . . .
H4 H 0.4278 0.5582 0.3430 0.029 Uiso 1 1 calc R . .
C5 C 0.2921(5) 0.39100(16) 0.30941(9) 0.0222(4) Uani 1 1 d . . .
H5 H 0.1849 0.4165 0.2705 0.027 Uiso 1 1 calc R . .
C6 C 0.3096(5) 0.26915(16) 0.32511(9) 0.0197(4) Uani 1 1 d . . .
C7 C 0.1393(5) 0.17513(17) 0.28242(10) 0.0236(4) Uani 1 1 d . . .
N1 N 0.4663(4) 0.22822(12) 0.37820(7) 0.0185(4) Uani 1 1 d . . .
O1 O 0.8888(4) 0.33640(11) 0.51891(6) 0.0264(3) Uani 1 1 d . . .
H1O H 0.9778 0.3011 0.5507 0.040 Uiso 1 1 calc R . .
O2 O 0.8008(4) 0.14678(11) 0.48553(6) 0.0256(3) Uani 1 1 d . . .
O3 O 0.1490(4) 0.06145(11) 0.30146(7) 0.0301(4) Uani 1 1 d . . .
H3O H 0.2532 0.0578 0.3371 0.045 Uiso 1 1 calc R . .
O4 O -0.0127(4) 0.20156(13) 0.23278(6) 0.0308(4) Uani 1 1 d . . .
O1W O 0.4469(4) -0.02963(13) 0.40792(7) 0.0289(4) Uani 1 1 d . . .
H1W1 H 0.565(8) 0.036(3) 0.4307(14) 0.073(9) Uiso 1 1 d . . .
H1W2 H 0.112(8) 0.251(2) 0.1506(15) 0.058(9) Uiso 1 1 d . . .
O2W O 0.1966(4) 0.25873(15) 0.11535(8) 0.0321(4) Uani 1 1 d . . .
H2W1 H 0.303(8) -0.062(3) 0.4348(15) 0.074(10) Uiso 1 1 d . . .
H2W2 H 0.282(7) 0.335(2) 0.1115(12) 0.051(8) Uiso 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 0.0180(10) 0.0230(11) 0.0166(11) -0.0026(8) 0.0021(7) -0.0034(7)
C2 0.0145(9) 0.0237(10) 0.0170(11) 0.0004(8) 0.0022(7) -0.0007(6)
C3 0.0188(10) 0.0207(10) 0.0232(11) -0.0030(8) 0.0020(7) -0.0031(7)
C4 0.0236(10) 0.0190(10) 0.0294(12) 0.0035(8) 0.0006(8) 0.0012(7)
C5 0.0201(10) 0.0277(11) 0.0187(11) 0.0056(8) -0.0007(7) 0.0021(7)
C6 0.0166(10) 0.0250(10) 0.0175(11) -0.0011(8) 0.0004(7) -0.0003(7)
C7 0.0212(11) 0.0304(11) 0.0193(12) -0.0011(9) 0.0014(8) 0.0002(8)
N1 0.0176(8) 0.0215(8) 0.0166(9) -0.0012(7) 0.0012(6) -0.0015(6)
O1 0.0345(8) 0.0255(7) 0.0183(8) 0.0000(6) -0.0078(6) -0.0022(5)
O2 0.0356(8) 0.0189(7) 0.0217(8) 0.0013(6) -0.0041(6) -0.0015(5)
O3 0.0413(9) 0.0241(8) 0.0240(9) -0.0036(6) -0.0074(6) -0.0043(6)
O4 0.0331(9) 0.0403(9) 0.0179(9) 0.0002(6) -0.0070(6) -0.0024(6)
O1W 0.0386(9) 0.0223(8) 0.0254(9) 0.0002(7) -0.0014(7) -0.0031(6)
O2W 0.0422(9) 0.0327(9) 0.0210(10) 0.0008(7) -0.0015(7) -0.0070(6)

_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 O2 1.221(2) . ?
C1 O1 1.311(2) . ?
C1 C2 1.497(3) . ?
C2 N1 1.342(2) . ?
C2 C3 1.389(3) . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(2) . ?
C5 H5 0.9500 . ?
C6 N1 1.332(2) . ?
C6 C7 1.502(3) . ?
C7 O4 1.215(2) . ?
C7 O3 1.322(2) . ?
O1 H1O 0.8400 . ?
O3 H3O 0.8400 . ?
O1W H1W1 0.96(3) . ?
O1W H2W1 0.88(3) . ?
O2W H1W2 0.84(3) . ?
O2W H2W2 0.90(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
O2 C1 O1 123.87(17) . . ?
O2 C1 C2 122.33(16) . . ?
O1 C1 C2 113.80(15) . . ?
N1 C2 C3 122.67(17) . . ?
N1 C2 C1 114.40(15) . . ?
C3 C2 C1 122.93(16) . . ?
C4 C3 C2 118.56(17) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C5 C4 C3 119.24(17) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 118.12(17) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C5 123.42(16) . . ?
N1 C6 C7 115.91(16) . . ?
C5 C6 C7 120.65(17) . . ?
O4 C7 O3 120.37(17) . . ?
O4 C7 C6 121.92(17) . . ?
O3 C7 C6 117.68(17) . . ?
C6 N1 C2 117.95(15) . . ?
C1 O1 H1O 109.5 . . ?
C7 O3 H3O 109.5 . . ?
H1W1 O1W H2W1 104(2) . . ?
H1W2 O2W H2W2 109(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
O3 H3O O1W 0.84 1.91 2.6835(19) 152.4 .
O1 H1O O2W 0.84 1.70 2.539(2) 173.5 4_666
O1W H1W1 O2 0.96(3) 1.88(3) 2.8372(19) 171(2) .
O1W H2W1 O2 0.88(3) 2.01(3) 2.827(2) 154(3) 3_656
O2W H2W2 O1W 0.90(3) 1.86(3) 2.738(2) 165(2) 2_655
O2W H1W2 O4 0.84(3) 1.93(3) 2.755(2) 167(3) .

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full 27.48
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max 0.241
_refine_diff_density_min -0.238
_refine_diff_density_rms 0.059


data_s93
_database_code_depnum_ccdc_archive 'CCDC 292210'

_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C7 H6 Cl N O5'
_chemical_formula_weight 219.58

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'
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)

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

_cell_length_a 5.1793(2)
_cell_length_b 9.4760(3)
_cell_length_c 8.5004(3)
_cell_angle_alpha 90.00
_cell_angle_beta 94.289(2)
_cell_angle_gamma 90.00
_cell_volume 416.02(3)
_cell_formula_units_Z 2
_cell_measurement_temperature 120(2)
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?

_exptl_crystal_description Plate
_exptl_crystal_colour Colourless
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.18
_exptl_crystal_size_min 0.03
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.753
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 224
_exptl_absorpt_coefficient_mu 0.454
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_min 0.9147
_exptl_absorpt_correction_T_max 0.9865
_exptl_absorpt_process_details 'SORTAV Blessing (1997)'
_exptl_special_details
;
PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
the entire data set is used to refine the cell, which is indexed from all
observed reflections in a 10 degree phi range.
;
_diffrn_ambient_temperature 120(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Nonius KappaCCD Area Detector'
_diffrn_measurement_method '\f and \w scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 5401
_diffrn_reflns_av_R_equivalents 0.0491
_diffrn_reflns_av_sigmaI/netI 0.0430
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_theta_min 3.22
_diffrn_reflns_theta_max 27.48
_reflns_number_total 1880
_reflns_number_gt 1821
_reflns_threshold_expression >2sigma(I)

_computing_data_collection ' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)'
_computing_molecular_graphics 'PLATON (Spek, 1990)'
_computing_publication_material ?

_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0400P)^2^+0.0555P] where P=(Fo^2^+2Fc^2^)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.28(5)
_refine_ls_number_reflns 1880
_refine_ls_number_parameters 138
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0316
_refine_ls_R_factor_gt 0.0294
_refine_ls_wR_factor_ref 0.0735
_refine_ls_wR_factor_gt 0.0717
_refine_ls_goodness_of_fit_ref 1.063
_refine_ls_restrained_S_all 1.063
_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
Cl1 Cl 0.53151(7) -1.80230(5) -1.03897(5) 0.02043(13) Uani 1 1 d . . .
C5 C 0.1930(4) -1.6892(2) -0.8480(3) 0.0166(4) Uani 1 1 d . . .
H5 H 0.2521 -1.5991 -0.8784 0.020 Uiso 1 1 calc R . .
C3 C 0.2088(4) -1.9410(2) -0.8572(3) 0.0150(4) Uani 1 1 d . . .
H3 H 0.2781 -2.0263 -0.8949 0.018 Uiso 1 1 calc R . .
N1 N -0.0899(3) -1.82589(16) -0.69506(16) 0.0147(3) Uani 1 1 d . . .
O2 O -0.2625(3) -2.09154(16) -0.61441(18) 0.0246(3) Uani 1 1 d . . .
O1 O 0.0377(3) -2.18815(14) -0.75790(18) 0.0236(4) Uani 1 1 d . . .
H1 H -0.0317 -2.2644 -0.7336 0.035 Uiso 1 1 calc R . .
O4 O -0.0410(3) -1.45545(15) -0.73571(19) 0.0251(3) Uani 1 1 d . . .
C6 C -0.0004(4) -1.7023(2) -0.7445(2) 0.0144(4) Uani 1 1 d . . .
O3 O -0.3035(3) -1.58318(14) -0.59499(17) 0.0230(3) Uani 1 1 d . . .
H3A H -0.3656 -1.5038 -0.5752 0.034 Uiso 1 1 calc R . .
C4 C 0.2964(3) -1.8109(2) -0.90530(17) 0.0159(3) Uani 1 1 d . . .
C7 C -0.1197(4) -1.56798(18) -0.6887(3) 0.0151(4) Uani 1 1 d . . .
C2 C 0.0159(4) -1.9422(2) -0.7518(2) 0.0155(4) Uani 1 1 d . . .
C1 C -0.0868(4) -2.08161(18) -0.6984(2) 0.0149(4) Uani 1 1 d . . .
O1W O -0.4877(3) -2.35122(19) -0.52141(19) 0.0289(4) Uani 1 1 d . . .
H1WB H -0.605(5) -2.347(4) -0.467(3) 0.042(8) Uiso 1 1 d . . .
H1WA H -0.420(6) -2.254(4) -0.547(3) 0.050(9) Uiso 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
Cl1 0.0201(2) 0.0190(2) 0.0237(2) 0.00200(18) 0.01195(15) -0.0013(2)
C5 0.0195(10) 0.0116(8) 0.0187(10) 0.0017(7) 0.0011(8) -0.0038(7)
C3 0.0168(10) 0.0101(8) 0.0189(10) -0.0010(7) 0.0063(8) 0.0008(7)
N1 0.0173(6) 0.0103(7) 0.0169(6) -0.0003(6) 0.0036(5) 0.0005(6)
O2 0.0294(8) 0.0128(7) 0.0341(8) 0.0014(6) 0.0187(6) -0.0013(6)
O1 0.0321(9) 0.0079(6) 0.0329(9) 0.0013(6) 0.0166(7) -0.0010(6)
O4 0.0315(8) 0.0112(7) 0.0346(9) -0.0001(6) 0.0165(7) 0.0003(6)
C6 0.0167(10) 0.0133(8) 0.0137(10) -0.0004(7) 0.0036(7) 0.0004(7)
O3 0.0270(7) 0.0111(7) 0.0329(8) -0.0009(6) 0.0155(6) 0.0024(6)
C4 0.0158(7) 0.0172(9) 0.0152(7) 0.0015(8) 0.0058(6) 0.0007(9)
C7 0.0171(9) 0.0114(10) 0.0171(9) -0.0013(7) 0.0024(7) -0.0012(7)
C2 0.0167(10) 0.0096(8) 0.0200(11) 0.0022(7) 0.0010(8) -0.0005(7)
C1 0.0177(9) 0.0089(9) 0.0186(9) -0.0021(8) 0.0053(7) 0.0011(7)
O1W 0.0329(8) 0.0131(8) 0.0443(9) 0.0006(6) 0.0262(7) 0.0012(6)

_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 C4 1.7282(16) . ?
C5 C4 1.376(3) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C3 C4 1.386(3) . ?
C3 C2 1.391(3) . ?
C3 H3 0.9500 . ?
N1 C2 1.337(2) . ?
N1 C6 1.339(2) . ?
O2 C1 1.202(2) . ?
O1 C1 1.319(2) . ?
O1 H1 0.8400 . ?
O4 C7 1.220(2) . ?
C6 C7 1.506(3) . ?
O3 C7 1.295(3) . ?
O3 H3A 0.8400 . ?
C2 C1 1.506(3) . ?
O1W H1WB 0.79(3) . ?
O1W H1WA 1.01(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C5 C6 117.96(16) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C4 C3 C2 117.68(18) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C2 N1 C6 116.58(14) . . ?
C1 O1 H1 109.5 . . ?
N1 C6 C5 124.07(17) . . ?
N1 C6 C7 118.72(17) . . ?
C5 C6 C7 117.19(17) . . ?
C7 O3 H3A 109.5 . . ?
C5 C4 C3 119.74(14) . . ?
C5 C4 Cl1 120.37(14) . . ?
C3 C4 Cl1 119.89(14) . . ?
O4 C7 O3 125.3(2) . . ?
O4 C7 C6 118.7(2) . . ?
O3 C7 C6 115.95(16) . . ?
N1 C2 C3 123.96(17) . . ?
N1 C2 C1 116.81(17) . . ?
C3 C2 C1 119.23(17) . . ?
O2 C1 O1 125.56(18) . . ?
O2 C1 C2 123.21(17) . . ?
O1 C1 C2 111.22(18) . . ?
H1WB O1W H1WA 112(3) . . ?

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 O4 0.84 1.81 2.5747(17) 150.3 1_545
O3 H3A O1W 0.84 1.66 2.494(2) 175.4 1_565
O1W H1WB N1 0.79(3) 2.19(3) 2.972(2) 175(3) 2_444
O1W H1WB O2 0.79(3) 2.53(3) 2.901(2) 111(3) 2_444
O1W H1WA O1 1.01(4) 3.14(3) 3.828(2) 126(2) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.212
_refine_diff_density_min -0.319
_refine_diff_density_rms 0.057



