# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350

_publ_section_title              
;Crystal structures and characterization of the
polymorphs of (2-furyl)oxoacetamide
;
_publ_contact_author_name        'Prof. Joel Bernstein'
_publ_contact_author_email       YOEL@BGU.AC.IL
loop_
_publ_author_name
I.Barsky
J.Bernstein

# Attachment 'Form_I.cif'

data_2ffo11
_database_code_depnum_ccdc_archive 'CCDC 659328'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H5 N O3'
_chemical_formula_weight         139.11

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           Orthorhombic
_symmetry_space_group_name_H-M   Fdd2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   39.698(16)
_cell_length_b                   48.359(19)
_cell_length_c                   3.8476(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7386(5)
_cell_formula_units_Z            48
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3456
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10577
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_sigmaI/netI    0.1090
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -60
_diffrn_reflns_limit_k_max       63
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         1.33
_diffrn_reflns_theta_max         28.39
_reflns_number_total             3714
_reflns_number_gt                1781
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0181P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.8(11)
_refine_ls_number_reflns         3714
_refine_ls_number_parameters     331
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0612
_refine_ls_wR_factor_gt          0.0513
_refine_ls_goodness_of_fit_ref   0.813
_refine_ls_restrained_S_all      0.813
_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
C1 C 0.13551(7) 0.00796(6) -0.0096(9) 0.0503(9) Uani 1 1 d . . .
C2 C 0.15327(8) 0.02646(6) 0.1705(9) 0.0522(9) Uani 1 1 d . . .
C3 C 0.13323(7) 0.05007(6) 0.1950(9) 0.0457(8) Uani 1 1 d . . .
C4 C 0.10407(6) 0.04473(5) 0.0260(8) 0.0374(7) Uani 1 1 d . . .
C5 C 0.07370(7) 0.06008(5) -0.0572(9) 0.0441(8) Uani 1 1 d . . .
C6 C 0.07129(8) 0.08954(5) 0.0877(9) 0.0502(9) Uani 1 1 d . . .
C7 C 0.20954(7) 0.12375(6) 0.8170(9) 0.0529(9) Uani 1 1 d . . .
C8 C 0.18749(7) 0.10366(6) 0.8720(8) 0.0486(9) Uani 1 1 d . . .
C9 C 0.20269(7) 0.07936(6) 0.7457(8) 0.0427(8) Uani 1 1 d . . .
C10 C 0.23304(6) 0.08623(5) 0.6149(8) 0.0374(7) Uani 1 1 d . . .
C11 C 0.25998(6) 0.07213(5) 0.4357(8) 0.0376(7) Uani 1 1 d . . .
C12 C 0.25676(6) 0.04087(5) 0.3769(8) 0.0372(7) Uani 1 1 d . . .
C13 C 0.47568(8) 0.03898(7) 0.7172(11) 0.0697(11) Uani 1 1 d . . .
C14 C 0.45834(8) 0.01978(7) 0.8860(10) 0.0643(11) Uani 1 1 d . . .
C15 C 0.42539(7) 0.03024(6) 0.9137(8) 0.0493(9) Uani 1 1 d . . .
C16 C 0.42480(6) 0.05508(5) 0.7615(8) 0.0406(7) Uani 1 1 d . . .
C17 C 0.39923(6) 0.07585(5) 0.6954(8) 0.0413(8) Uani 1 1 d . . .
C18 C 0.36427(6) 0.07185(5) 0.8614(7) 0.0407(8) Uani 1 1 d . . .
H1 H 0.1390(5) -0.0111(4) -0.078(7) 0.058(9) Uiso 1 1 d . . .
H2 H 0.1734(5) 0.0241(4) 0.265(7) 0.043(8) Uiso 1 1 d . . .
H3 H 0.1379(4) 0.0673(3) 0.291(6) 0.024(6) Uiso 1 1 d . . .
H4 H 0.0383(7) 0.1156(5) 0.066(10) 0.086(15) Uiso 1 1 d . . .
H5 H 0.0276(9) 0.0888(7) -0.116(13) 0.17(2) Uiso 1 1 d . . .
H6 H 0.2097(5) 0.1437(5) 0.858(8) 0.071(9) Uiso 1 1 d . . .
H7 H 0.1667(5) 0.1069(4) 0.970(8) 0.057(9) Uiso 1 1 d . . .
H8 H 0.1936(5) 0.0626(4) 0.750(7) 0.056(9) Uiso 1 1 d . . .
H9 H 0.2834(5) 0.0110(4) 0.150(7) 0.050(9) Uiso 1 1 d . . .
H10 H 0.3008(6) 0.0402(5) 0.187(10) 0.102(13) Uiso 1 1 d . . .
H11 H 0.4978(6) 0.0401(4) 0.638(8) 0.069(10) Uiso 1 1 d . . .
H12 H 0.4666(6) 0.0031(4) 0.958(8) 0.065(10) Uiso 1 1 d . . .
H13 H 0.4094(4) 0.0218(3) 1.012(6) 0.018(7) Uiso 1 1 d . . .
H14 H 0.3267(7) 0.0931(5) 0.927(10) 0.103(15) Uiso 1 1 d . . .
H15 H 0.3531(5) 0.1101(4) 0.728(7) 0.061(9) Uiso 1 1 d . . .
N1 N 0.04207(8) 0.10156(7) -0.0017(9) 0.0775(11) Uani 1 1 d . . .
N2 N 0.28318(6) 0.02968(5) 0.2219(8) 0.0539(8) Uani 1 1 d . . .
N3 N 0.34514(7) 0.09410(5) 0.8389(8) 0.0547(8) Uani 1 1 d . . .
O1 O 0.10510(4) 0.01822(3) -0.1023(5) 0.0492(6) Uani 1 1 d . . .
O2 O 0.05064(4) 0.05069(3) -0.2327(6) 0.0627(7) Uani 1 1 d . . .
O3 O 0.09353(5) 0.10003(4) 0.2596(6) 0.0771(7) Uani 1 1 d . . .
O4 O 0.23784(4) 0.11423(3) 0.6557(5) 0.0531(6) Uani 1 1 d . . .
O5 O 0.28457(4) 0.08448(3) 0.3208(6) 0.0538(6) Uani 1 1 d . . .
O6 O 0.23139(4) 0.02846(3) 0.4700(6) 0.0520(6) Uani 1 1 d . . .
O7 O 0.45650(4) 0.06118(3) 0.6318(6) 0.0609(6) Uani 1 1 d . . .
O8 O 0.40435(4) 0.09623(3) 0.5169(6) 0.0590(6) Uani 1 1 d . . .
O9 O 0.35576(4) 0.05035(3) 1.0025(5) 0.0555(6) Uani 1 1 d . . .


_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 1.333(4) . ?
C1 O1 1.353(3) . ?
C2 C3 1.394(3) . ?
C3 C4 1.353(3) . ?
C4 O1 1.374(3) . ?
C4 C5 1.452(3) . ?
C5 O2 1.225(3) . ?
C5 C6 1.533(3) . ?
C6 O3 1.215(3) . ?
C6 N1 1.342(4) . ?
C7 C8 1.325(4) . ?
C7 O4 1.363(3) . ?
C8 C9 1.407(3) . ?
C9 C10 1.347(3) . ?
C10 O4 1.376(3) . ?
C10 C11 1.444(3) . ?
C11 O5 1.227(2) . ?
C11 C12 1.534(3) . ?
C12 O6 1.226(3) . ?
C12 N2 1.322(3) . ?
C13 C14 1.326(4) . ?
C13 O7 1.356(3) . ?
C14 C15 1.407(4) . ?
C15 C16 1.337(3) . ?
C16 O7 1.385(3) . ?
C16 C17 1.451(3) . ?
C17 O8 1.218(3) . ?
C17 C18 1.540(3) . ?
C18 O9 1.220(3) . ?
C18 N3 1.320(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 O1 111.3(3) . . ?
C1 C2 C3 106.5(3) . . ?
C4 C3 C2 107.4(3) . . ?
C3 C4 O1 109.0(2) . . ?
C3 C4 C5 136.0(2) . . ?
O1 C4 C5 115.0(2) . . ?
O2 C5 C4 123.6(2) . . ?
O2 C5 C6 119.9(3) . . ?
C4 C5 C6 116.6(3) . . ?
O3 C6 N1 125.9(3) . . ?
O3 C6 C5 122.8(3) . . ?
N1 C6 C5 111.3(3) . . ?
C8 C7 O4 111.7(3) . . ?
C7 C8 C9 105.9(3) . . ?
C10 C9 C8 107.8(3) . . ?
C9 C10 O4 108.9(2) . . ?
C9 C10 C11 136.4(3) . . ?
O4 C10 C11 114.6(2) . . ?
O5 C11 C10 122.1(2) . . ?
O5 C11 C12 119.5(2) . . ?
C10 C11 C12 118.3(2) . . ?
O6 C12 N2 125.7(2) . . ?
O6 C12 C11 120.5(2) . . ?
N2 C12 C11 113.8(2) . . ?
C14 C13 O7 112.4(3) . . ?
C13 C14 C15 105.5(3) . . ?
C16 C15 C14 107.8(3) . . ?
C15 C16 O7 109.5(2) . . ?
C15 C16 C17 135.3(3) . . ?
O7 C16 C17 115.2(2) . . ?
O8 C17 C16 122.8(2) . . ?
O8 C17 C18 119.1(2) . . ?
C16 C17 C18 118.1(2) . . ?
O9 C18 N3 124.4(3) . . ?
O9 C18 C17 122.7(2) . . ?
N3 C18 C17 112.9(3) . . ?
C1 O1 C4 105.9(2) . . ?
C7 O4 C10 105.6(2) . . ?
C13 O7 C16 104.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -0.1(4) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 O1 0.5(3) . . . . ?
C2 C3 C4 C5 -177.2(3) . . . . ?
C3 C4 C5 O2 176.5(3) . . . . ?
O1 C4 C5 O2 -1.1(4) . . . . ?
C3 C4 C5 C6 -3.6(5) . . . . ?
O1 C4 C5 C6 178.8(2) . . . . ?
O2 C5 C6 O3 -179.1(3) . . . . ?
C4 C5 C6 O3 1.0(4) . . . . ?
O2 C5 C6 N1 0.7(4) . . . . ?
C4 C5 C6 N1 -179.2(3) . . . . ?
O4 C7 C8 C9 1.4(4) . . . . ?
C7 C8 C9 C10 -1.1(4) . . . . ?
C8 C9 C10 O4 0.4(3) . . . . ?
C8 C9 C10 C11 -176.2(3) . . . . ?
C9 C10 C11 O5 174.4(3) . . . . ?
O4 C10 C11 O5 -2.1(4) . . . . ?
C9 C10 C11 C12 -3.3(5) . . . . ?
O4 C10 C11 C12 -179.8(2) . . . . ?
O5 C11 C12 O6 -175.3(3) . . . . ?
C10 C11 C12 O6 2.4(4) . . . . ?
O5 C11 C12 N2 4.6(4) . . . . ?
C10 C11 C12 N2 -177.7(3) . . . . ?
O7 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C14 C15 C16 O7 0.4(4) . . . . ?
C14 C15 C16 C17 178.3(3) . . . . ?
C15 C16 C17 O8 -172.4(3) . . . . ?
O7 C16 C17 O8 5.3(4) . . . . ?
C15 C16 C17 C18 8.0(5) . . . . ?
O7 C16 C17 C18 -174.3(2) . . . . ?
O8 C17 C18 O9 169.6(3) . . . . ?
C16 C17 C18 O9 -10.8(4) . . . . ?
O8 C17 C18 N3 -11.4(4) . . . . ?
C16 C17 C18 N3 168.2(3) . . . . ?
C2 C1 O1 C4 0.4(3) . . . . ?
C3 C4 O1 C1 -0.5(3) . . . . ?
C5 C4 O1 C1 177.7(2) . . . . ?
C8 C7 O4 C10 -1.2(3) . . . . ?
C9 C10 O4 C7 0.4(3) . . . . ?
C11 C10 O4 C7 177.9(2) . . . . ?
C14 C13 O7 C16 0.4(4) . . . . ?
C15 C16 O7 C13 -0.5(3) . . . . ?
C17 C16 O7 C13 -178.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        28.39
_diffrn_measured_fraction_theta_full 0.959
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.033

# Attachment 'Form_II.cif'

data_2ff2f1
_database_code_depnum_ccdc_archive 'CCDC 659329'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H5 N O3'
_chemical_formula_weight         139.11

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)

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

_cell_length_a                   3.7455(19)
_cell_length_b                   7.257(4)
_cell_length_c                   11.424(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.881(9)
_cell_angle_gamma                90.00
_cell_volume                     308.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             144
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1937
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         28.14
_reflns_number_total             1005
_reflns_number_gt                712
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0915P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(2)
_refine_ls_number_reflns         1005
_refine_ls_number_parameters     111
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1345
_refine_ls_wR_factor_gt          0.1262
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_restrained_S_all      0.927
_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 0.2114(11) 0.1290(6) 0.0696(4) 0.0551(10) Uani 1 1 d . . .
C2 C 0.0735(11) 0.0490(6) 0.1612(3) 0.0545(10) Uani 1 1 d . . .
C3 C 0.0953(10) 0.1834(5) 0.2530(3) 0.0489(9) Uani 1 1 d . . .
C4 C 0.2481(8) 0.3366(4) 0.2104(3) 0.0391(8) Uani 1 1 d . . .
C5 C 0.3443(8) 0.5187(5) 0.2549(3) 0.0402(8) Uani 1 1 d . . .
C6 C 0.2202(9) 0.5764(5) 0.3746(3) 0.0425(8) Uani 1 1 d . . .
H1 H 0.214(10) 0.101(6) -0.011(3) 0.059(12) Uiso 1 1 d . . .
H2 H -0.012(10) -0.069(7) 0.173(3) 0.058(11) Uiso 1 1 d . . .
H3 H 0.062(10) 0.157(6) 0.334(3) 0.053(11) Uiso 1 1 d . . .
H4 H 0.264(13) 0.794(8) 0.467(4) 0.076(15) Uiso 1 1 d . . .
H5 H 0.470(17) 0.817(10) 0.363(5) 0.12(2) Uiso 1 1 d . . .
N1 N 0.3048(10) 0.7508(5) 0.4004(3) 0.0582(10) Uani 1 1 d . . .
O1 O 0.3203(7) 0.3042(3) 0.0962(2) 0.0510(7) Uani 1 1 d . . .
O2 O 0.5166(7) 0.6285(4) 0.2016(2) 0.0554(7) Uani 1 1 d . . .
O3 O 0.0522(8) 0.4750(4) 0.4332(2) 0.0624(8) Uani 1 1 d . . .


_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 1.345(6) . ?
C1 O1 1.360(5) . ?
C2 C3 1.428(5) . ?
C3 C4 1.363(5) . ?
C4 O1 1.379(4) . ?
C4 C5 1.448(4) . ?
C5 O2 1.225(4) . ?
C5 C6 1.547(4) . ?
C6 O3 1.213(4) . ?
C6 N1 1.330(5) . ?

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 O1 111.1(4) . . ?
C1 C2 C3 106.2(4) . . ?
C4 C3 C2 106.8(3) . . ?
C3 C4 O1 109.2(3) . . ?
C3 C4 C5 135.8(3) . . ?
O1 C4 C5 115.0(3) . . ?
O2 C5 C4 122.9(3) . . ?
O2 C5 C6 119.0(3) . . ?
C4 C5 C6 118.1(3) . . ?
O3 C6 N1 125.4(4) . . ?
O3 C6 C5 122.9(3) . . ?
N1 C6 C5 111.6(3) . . ?
C1 O1 C4 106.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 0.1(5) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 O1 0.3(4) . . . . ?
C2 C3 C4 C5 179.5(4) . . . . ?
C3 C4 C5 O2 172.2(4) . . . . ?
O1 C4 C5 O2 -8.6(4) . . . . ?
C3 C4 C5 C6 -8.3(5) . . . . ?
O1 C4 C5 C6 170.8(3) . . . . ?
O2 C5 C6 O3 -179.2(3) . . . . ?
C4 C5 C6 O3 1.3(5) . . . . ?
O2 C5 C6 N1 4.0(4) . . . . ?
C4 C5 C6 N1 -175.5(3) . . . . ?
C2 C1 O1 C4 0.1(4) . . . . ?
C3 C4 O1 C1 -0.3(4) . . . . ?
C5 C4 O1 C1 -179.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        28.14
_diffrn_measured_fraction_theta_full 0.953
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.057


