# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk 
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
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data_shelxle
_database_code_depnum_ccdc_archive 'CCDC 900648'
#TrackingRef '- compound1.CIF'
#==========================================================================
_audit_creation_method           SHELXL-97
_audit_creation_date             '20 August 2008'
#==========================================================================
#==========================================================================
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 Cl N, C4 H3 O4, 0.5(C4 H4 O4)'
_chemical_formula_sum            'C19 H16 Cl N O6'
_chemical_formula_weight         389.78
_chemical_compound_source        Synthesis
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'
#========================================================================
# Crystal Data
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   8.6870(17)
_cell_length_b                   8.9000(18)
_cell_length_c                   13.039(3)
_cell_angle_alpha                104.06(3)
_cell_angle_beta                 97.67(3)
_cell_angle_gamma                105.15(3)
_cell_volume                     922.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    730
_cell_measurement_theta_min      1.52
_cell_measurement_theta_max      28.1
_exptl_crystal_description       Prism
_exptl_crystal_colour            'Pale Yellow'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_type   'Multi Scan'
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC7S Mercury'
_diffrn_measurement_method       '\w '
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Mercury (2x2 bin mode)'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13239
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         28.10
_reflns_number_total             3499
_reflns_number_gt                2296
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_structure_refinement  'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_molecular_graphics    
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND
(Brandenburg, 1998)
;
_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^)+(0.0432P)^2^+1.7336P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3499
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1409
_refine_ls_R_factor_gt           0.0957
_refine_ls_wR_factor_ref         0.2090
_refine_ls_wR_factor_gt          0.1819
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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
N1 N -0.0918(5) 0.0570(5) 0.8449(3) 0.0582(10) Uani 1 1 d . . .
H1N H -0.0405 0.0697 0.7941 0.070 Uiso 1 1 calc R . .
Cl1 Cl -0.6801(2) -0.47327(18) 1.06801(13) 0.0864(5) Uani 1 1 d . . .
O1 O 0.3581(5) 0.5879(5) 0.7568(3) 0.0901(13) Uani 1 1 d . . .
H1OH H 0.2678 0.4829 0.7729 0.108 Uiso 1 1 d R . .
O2 O 0.5121(6) 0.6483(5) 0.6428(4) 0.1212(19) Uani 1 1 d . . .
O3 O 0.1668(5) 0.3409(4) 0.7736(3) 0.0801(12) Uani 1 1 d . . .
O4 O 0.0691(4) 0.0814(4) 0.6850(3) 0.0644(9) Uani 1 1 d . . .
O5 O -0.0738(4) 0.1992(4) 0.4312(3) 0.0678(10) Uani 1 1 d . . .
H5OH H -0.0781 0.0941 0.3905 0.081 Uiso 1 1 d R . .
O6 O 0.0055(5) 0.2811(4) 0.2931(3) 0.0781(11) Uani 1 1 d . . .
C1 C -0.4371(6) -0.1398(6) 1.1021(4) 0.0547(12) Uani 1 1 d . . .
H1 H -0.4591 -0.2309 1.0429 0.066 Uiso 1 1 calc R . .
C2 C -0.3309(6) -0.0052(6) 1.0991(4) 0.0559(12) Uani 1 1 d . . .
H2 H -0.3056 0.0856 1.1589 0.067 Uiso 1 1 calc R . .
C3 C -0.5239(5) -0.1603(6) 1.1890(4) 0.0505(11) Uani 1 1 d . . .
C4 C -0.6371(6) -0.3074(6) 1.1830(4) 0.0555(12) Uani 1 1 d . . .
C5 C -0.7193(6) -0.3270(7) 1.2644(4) 0.0706(15) Uani 1 1 d . . .
H5 H -0.7921 -0.4276 1.2585 0.085 Uiso 1 1 calc R . .
C6 C -0.6941(7) -0.1987(7) 1.3537(4) 0.0730(15) Uani 1 1 d . . .
H6 H -0.7490 -0.2118 1.4090 0.088 Uiso 1 1 calc R . .
C7 C -0.5865(7) -0.0491(7) 1.3616(4) 0.0664(14) Uani 1 1 d . . .
H7A H -0.5719 0.0395 1.4211 0.080 Uiso 1 1 calc R . .
C8 C -0.5008(6) -0.0314(6) 1.2812(4) 0.0583(12) Uani 1 1 d . . .
H8 H -0.4260 0.0688 1.2886 0.070 Uiso 1 1 calc R . .
C9 C -0.2498(5) 0.0133(6) 1.0098(3) 0.0494(11) Uani 1 1 d . . .
C10 C -0.2874(6) -0.1072(6) 0.9121(4) 0.0552(12) Uani 1 1 d . . .
H10 H -0.3676 -0.2052 0.9017 0.066 Uiso 1 1 calc R . .
C11 C -0.2077(6) -0.0836(6) 0.8306(4) 0.0582(12) Uani 1 1 d . . .
H11 H -0.2342 -0.1653 0.7654 0.070 Uiso 1 1 calc R . .
C12 C -0.0546(6) 0.1772(7) 0.9363(4) 0.0644(13) Uani 1 1 d . . .
H12 H 0.0240 0.2748 0.9432 0.077 Uiso 1 1 calc R . .
C13 C -0.1297(6) 0.1600(6) 1.0204(4) 0.0597(13) Uani 1 1 d . . .
H13 H -0.1015 0.2449 1.0842 0.072 Uiso 1 1 calc R . .
C14 C 0.2528(6) 0.2441(6) 0.6101(4) 0.0556(12) Uani 1 1 d . . .
H14 H 0.2372 0.1491 0.5553 0.067 Uiso 1 1 calc R . .
C15 C 0.3559(6) 0.3768(6) 0.5998(4) 0.0628(13) Uani 1 1 d . . .
H15 H 0.3996 0.3590 0.5382 0.075 Uiso 1 1 calc R . .
C16 C 0.4131(7) 0.5464(7) 0.6685(5) 0.0737(15) Uani 1 1 d . . .
C17 C 0.1584(6) 0.2244(6) 0.6958(4) 0.0556(12) Uani 1 1 d . . .
C18 C 0.0006(6) 0.4786(6) 0.4485(4) 0.0549(12) Uani 1 1 d . . .
H18 H 0.0169 0.5597 0.4141 0.066 Uiso 1 1 calc R . .
C19 C -0.0220(6) 0.3111(6) 0.3827(4) 0.0543(11) 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
N1 0.059(2) 0.069(3) 0.050(2) 0.022(2) 0.0179(18) 0.017(2)
Cl1 0.0992(11) 0.0546(9) 0.0883(11) 0.0035(7) 0.0306(8) 0.0054(7)
O1 0.111(3) 0.051(2) 0.088(3) 0.002(2) 0.032(2) 0.003(2)
O2 0.148(4) 0.062(3) 0.123(4) 0.024(3) 0.047(3) -0.024(3)
O3 0.100(3) 0.050(2) 0.080(3) 0.0016(19) 0.044(2) 0.0075(19)
O4 0.077(2) 0.043(2) 0.071(2) 0.0142(17) 0.0324(18) 0.0094(16)
O5 0.094(3) 0.043(2) 0.061(2) 0.0076(16) 0.0293(18) 0.0123(17)
O6 0.118(3) 0.063(2) 0.052(2) 0.0084(18) 0.033(2) 0.027(2)
C1 0.063(3) 0.049(3) 0.050(3) 0.012(2) 0.014(2) 0.015(2)
C2 0.066(3) 0.054(3) 0.042(3) 0.008(2) 0.011(2) 0.014(2)
C3 0.057(3) 0.052(3) 0.047(3) 0.017(2) 0.013(2) 0.019(2)
C4 0.062(3) 0.051(3) 0.054(3) 0.018(2) 0.015(2) 0.014(2)
C5 0.069(3) 0.071(4) 0.072(4) 0.028(3) 0.023(3) 0.012(3)
C6 0.085(4) 0.084(4) 0.058(3) 0.031(3) 0.031(3) 0.023(3)
C7 0.082(4) 0.071(4) 0.048(3) 0.018(3) 0.015(2) 0.026(3)
C8 0.063(3) 0.062(3) 0.047(3) 0.014(2) 0.013(2) 0.013(2)
C9 0.052(3) 0.053(3) 0.044(3) 0.018(2) 0.0101(19) 0.013(2)
C10 0.060(3) 0.053(3) 0.052(3) 0.017(2) 0.017(2) 0.013(2)
C11 0.067(3) 0.056(3) 0.051(3) 0.012(2) 0.013(2) 0.021(2)
C12 0.060(3) 0.067(4) 0.056(3) 0.015(3) 0.008(2) 0.006(2)
C13 0.065(3) 0.058(3) 0.048(3) 0.013(2) 0.010(2) 0.008(2)
C14 0.070(3) 0.046(3) 0.053(3) 0.017(2) 0.019(2) 0.016(2)
C15 0.066(3) 0.052(3) 0.062(3) 0.010(2) 0.014(2) 0.009(2)
C16 0.077(4) 0.056(3) 0.077(4) 0.016(3) 0.017(3) 0.005(3)
C17 0.065(3) 0.045(3) 0.054(3) 0.009(2) 0.013(2) 0.017(2)
C18 0.064(3) 0.044(3) 0.053(3) 0.011(2) 0.017(2) 0.011(2)
C19 0.063(3) 0.045(3) 0.050(3) 0.008(2) 0.015(2) 0.014(2)
_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
N1 C12 1.328(6) . ?
N1 C11 1.339(6) . ?
Cl1 C4 1.748(5) . ?
O1 C16 1.313(6) . ?
O2 C16 1.221(6) . ?
O3 C17 1.240(5) . ?
O4 C17 1.269(5) . ?
O5 C19 1.320(5) . ?
O6 C19 1.203(5) . ?
C1 C2 1.320(6) . ?
C1 C3 1.464(6) . ?
C2 C9 1.459(6) . ?
C3 C4 1.394(6) . ?
C3 C8 1.395(6) . ?
C4 C5 1.376(7) . ?
C5 C6 1.364(7) . ?
C6 C7 1.383(7) . ?
C7 C8 1.381(6) . ?
C9 C10 1.386(6) . ?
C9 C13 1.405(6) . ?
C10 C11 1.372(6) . ?
C12 C13 1.369(6) . ?
C14 C15 1.330(6) . ?
C14 C17 1.489(6) . ?
C15 C16 1.470(7) . ?
C18 C18 1.306(9) 2_566 ?
C18 C19 1.476(6) . ?
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
C12 N1 C11 121.2(4) . . ?
C2 C1 C3 126.6(5) . . ?
C1 C2 C9 125.5(4) . . ?
C4 C3 C8 116.4(4) . . ?
C4 C3 C1 122.1(4) . . ?
C8 C3 C1 121.4(4) . . ?
C5 C4 C3 122.3(5) . . ?
C5 C4 Cl1 118.1(4) . . ?
C3 C4 Cl1 119.6(4) . . ?
C6 C5 C4 120.0(5) . . ?
C5 C6 C7 119.7(5) . . ?
C8 C7 C6 120.0(5) . . ?
C7 C8 C3 121.5(5) . . ?
C10 C9 C13 117.2(4) . . ?
C10 C9 C2 123.1(4) . . ?
C13 C9 C2 119.7(4) . . ?
C11 C10 C9 120.8(4) . . ?
N1 C11 C10 120.0(4) . . ?
N1 C12 C13 121.3(5) . . ?
C12 C13 C9 119.5(5) . . ?
C15 C14 C17 130.0(5) . . ?
C14 C15 C16 131.5(5) . . ?
O2 C16 O1 120.3(5) . . ?
O2 C16 C15 119.5(6) . . ?
O1 C16 C15 120.2(5) . . ?
O3 C17 O4 121.8(5) . . ?
O3 C17 C14 122.0(4) . . ?
O4 C17 C14 116.2(4) . . ?
C18 C18 C19 124.9(6) 2_566 . ?
O6 C19 O5 123.7(4) . . ?
O6 C19 C18 122.4(5) . . ?
O5 C19 C18 113.9(4) . . ?
_diffrn_measured_fraction_theta_max 0.775
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.060


data_shelxla
_database_code_depnum_ccdc_archive 'CCDC 900649'
#TrackingRef '- compound2.CIF'
#==========================================================================
_audit_creation_method           SHELXL-97
_audit_creation_date             '20 August 2008'
#==========================================================================
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 N2, C4 H4 O4, C4 H2 O4'
_chemical_formula_sum            'C20 H18 N2 O8'
_chemical_formula_weight         414.36
_chemical_compound_source        Synthesis
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           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   3.880(3)
_cell_length_b                   10.058(6)
_cell_length_c                   12.438(9)
_cell_angle_alpha                76.64(3)
_cell_angle_beta                 88.30(4)
_cell_angle_gamma                82.26(4)
_cell_volume                     468.0(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    646
_cell_measurement_theta_min      1.85
_cell_measurement_theta_max      27.62
_exptl_crystal_description       Prism
_exptl_crystal_colour            'Pale Yellow'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             216
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   'Multi Scan'
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC7S Mercury'
_diffrn_measurement_method       '\w '
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Mercury (2x2 bin mode)'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5159
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         27.62
_reflns_number_total             1687
_reflns_number_gt                1216
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_structure_refinement  'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_molecular_graphics    
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND
(Brandenburg, 1998)
;
_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^)+(0.0684P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1687
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.1241
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
N1 N 1.2164(4) 0.37964(17) 0.18616(13) 0.0407(5) Uani 1 1 d . . .
H1N H 1.2243 0.3217 0.1447 0.049 Uiso 1 1 calc R . .
O1 O 1.5992(4) 0.86450(16) 0.30997(12) 0.0562(5) Uani 1 1 d . . .
H1OH H 1.7179 0.9565 0.2703 0.067 Uiso 1 1 d R . .
O2 O 1.3347(4) 0.78015(17) 0.46496(14) 0.0690(6) Uani 1 1 d . . .
O3 O 1.1518(4) 0.19914(15) 0.07011(11) 0.0533(5) Uani 1 1 d . . .
O4 O 0.8992(4) 0.07681(16) 0.21511(12) 0.0567(5) Uani 1 1 d . . .
C1 C 1.4597(5) 0.5413(2) 0.03308(17) 0.0459(6) Uani 1 1 d . . .
H1 H 1.4933 0.6329 0.0064 0.055 Uiso 1 1 calc R . .
C2 C 1.3213(5) 0.5044(2) 0.14532(16) 0.0397(5) Uani 1 1 d . . .
C3 C 1.1011(5) 0.3449(2) 0.28944(17) 0.0485(6) Uani 1 1 d . . .
H3 H 1.0333 0.2580 0.3154 0.058 Uiso 1 1 calc R . .
C4 C 1.0796(5) 0.4340(2) 0.35845(18) 0.0538(6) Uani 1 1 d . . .
H4 H 1.0009 0.4084 0.4307 0.065 Uiso 1 1 calc R . .
C5 C 1.1780(5) 0.5623(2) 0.31761(19) 0.0563(6) Uani 1 1 d . . .
H5 H 1.1645 0.6255 0.3621 0.068 Uiso 1 1 calc R . .
C6 C 1.2954(5) 0.5967(2) 0.21171(18) 0.0502(6) Uani 1 1 d . . .
H6 H 1.3588 0.6841 0.1841 0.060 Uiso 1 1 calc R . .
C10 C 1.5506(5) 0.9918(2) 0.45099(16) 0.0420(5) Uani 1 1 d . . .
H10 H 1.6670 1.0585 0.4056 0.050 Uiso 1 1 calc R . .
C9 C 1.4854(5) 0.8704(2) 0.41020(17) 0.0447(5) Uani 1 1 d . . .
C8 C 0.9487(4) -0.0046(2) 0.05135(15) 0.0420(5) Uani 1 1 d . . .
H8 H 0.8355 -0.0794 0.0848 0.050 Uiso 1 1 calc R . .
C7 C 1.0016(5) 0.0964(2) 0.11764(16) 0.0406(5) 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
N1 0.0556(10) 0.0375(12) 0.0341(10) -0.0157(8) 0.0052(7) -0.0121(7)
O1 0.0853(10) 0.0506(11) 0.0425(9) -0.0238(8) 0.0143(7) -0.0242(8)
O2 0.1066(12) 0.0555(12) 0.0580(11) -0.0218(9) 0.0243(9) -0.0467(10)
O3 0.0807(10) 0.0449(10) 0.0434(10) -0.0181(7) 0.0155(7) -0.0305(7)
O4 0.0912(10) 0.0531(11) 0.0359(9) -0.0204(7) 0.0195(7) -0.0316(8)
C1 0.0556(12) 0.0397(14) 0.0436(14) -0.0083(9) 0.0039(9) -0.0138(9)
C2 0.0456(10) 0.0395(13) 0.0355(11) -0.0087(9) 0.0043(8) -0.0121(8)
C3 0.0665(13) 0.0411(14) 0.0402(13) -0.0081(10) 0.0080(10) -0.0192(10)
C4 0.0766(14) 0.0557(17) 0.0353(13) -0.0160(11) 0.0145(10) -0.0243(11)
C5 0.0803(15) 0.0512(17) 0.0470(14) -0.0244(12) 0.0131(11) -0.0229(12)
C6 0.0677(13) 0.0391(14) 0.0492(14) -0.0142(11) 0.0105(10) -0.0212(10)
C10 0.0544(12) 0.0366(13) 0.0386(12) -0.0104(10) 0.0088(9) -0.0173(8)
C9 0.0580(11) 0.0396(14) 0.0417(13) -0.0152(10) 0.0050(9) -0.0156(9)
C8 0.0538(12) 0.0395(13) 0.0378(11) -0.0146(10) 0.0076(9) -0.0160(9)
C7 0.0534(11) 0.0361(13) 0.0362(12) -0.0132(10) 0.0080(8) -0.0129(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
N1 C3 1.332(3) . ?
N1 C2 1.352(3) . ?
N1 H1N 0.8600 . ?
O1 C9 1.322(3) . ?
O1 H1OH 1.0959 . ?
O2 C9 1.210(3) . ?
O3 C7 1.272(2) . ?
O4 C7 1.244(2) . ?
C1 C1 1.302(4) 2_865 ?
C1 C2 1.465(3) . ?
C1 H1 0.9300 . ?
C2 C6 1.371(3) . ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.363(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C10 C10 1.309(4) 2_876 ?
C10 C9 1.479(3) . ?
C10 H10 0.9300 . ?
C8 C8 1.313(4) 2_755 ?
C8 C7 1.486(3) . ?
C8 H8 0.9300 . ?
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
C3 N1 C2 121.16(18) . . ?
C3 N1 H1N 119.4 . . ?
C2 N1 H1N 119.4 . . ?
C9 O1 H1OH 111.5 . . ?
C1 C1 C2 126.5(3) 2_865 . ?
C1 C1 H1 116.7 2_865 . ?
C2 C1 H1 116.7 . . ?
N1 C2 C6 118.4(2) . . ?
N1 C2 C1 121.39(19) . . ?
C6 C2 C1 120.23(19) . . ?
N1 C3 C4 121.7(2) . . ?
N1 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 117.9(2) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C2 120.9(2) . . ?
C5 C6 H6 119.5 . . ?
C2 C6 H6 119.5 . . ?
C10 C10 C9 122.1(2) 2_876 . ?
C10 C10 H10 119.0 2_876 . ?
C9 C10 H10 119.0 . . ?
O2 C9 O1 120.8(2) . . ?
O2 C9 C10 122.3(2) . . ?
O1 C9 C10 116.89(17) . . ?
C8 C8 C7 124.3(2) 2_755 . ?
C8 C8 H8 117.8 2_755 . ?
C7 C8 H8 117.8 . . ?
O4 C7 O3 123.70(18) . . ?
O4 C7 C8 119.24(17) . . ?
O3 C7 C8 117.07(18) . . ?
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
C3 N1 C2 C6 -2.2(3) . . . . ?
C3 N1 C2 C1 177.86(15) . . . . ?
C1 C1 C2 N1 -9.6(4) 2_865 . . . ?
C1 C1 C2 C6 170.5(2) 2_865 . . . ?
C2 N1 C3 C4 0.7(3) . . . . ?
N1 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C2 -0.8(3) . . . . ?
N1 C2 C6 C5 2.2(3) . . . . ?
C1 C2 C6 C5 -177.80(17) . . . . ?
C10 C10 C9 O2 0.2(4) 2_876 . . . ?
C10 C10 C9 O1 -180.0(2) 2_876 . . . ?
C8 C8 C7 O4 -178.8(2) 2_755 . . . ?
C8 C8 C7 O3 1.1(4) 2_755 . . . ?
_diffrn_measured_fraction_theta_max 0.778
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.944
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.046