# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Alexander Briceno'
_publ_contact_author_email       ABRICENO@IVIC.VE

_publ_section_title              
;
Concomitant [2+2] cycloaddition solid state reactions
from organic co-crystals self-assembled via mechanochemistry
;
loop_
_publ_author_name
A.Briceno
'Carlos Avendano'

# Attachment 'SHELXLEC2.CIF'

data_c2c-p
_database_code_depnum_ccdc_archive 'CCDC 704338'

#==========================================================================

_audit_creation_method           SHELXL-97
_audit_creation_date             '20 August 2008'

#==========================================================================

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N2, C4 H4 O4'
_chemical_formula_sum            'C16 H14 N2 O4'
_chemical_formula_weight         298.29
_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           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  -C2yc

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

_cell_length_a                   22.911(11)
_cell_length_b                   3.9313(15)
_cell_length_c                   18.607(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.067(10)
_cell_angle_gamma                90.00
_cell_volume                     1464.9(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    837
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      26.10

_exptl_crystal_description       Prism
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   'Multi Scan'
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_T_max  0.946
_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       'ω '
_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            7548
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_sigmaI/netI    0.0637
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         28.13
_reflns_number_total             1457
_reflns_number_gt                962
_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)
;
_computing_publication_material  
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003).
;

_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)+(0.0741P)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     SHELXL
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1457
_refine_ls_number_parameters     105
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1566
_refine_ls_wR_factor_gt          0.1326
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.13095(8) 0.4271(4) 0.35922(9) 0.0499(5) Uani 1 1 d . . .
O1 O 0.12888(8) 0.3319(4) 0.55240(8) 0.0775(6) Uani 1 1 d . . .
O2 O 0.05758(7) 0.1931(4) 0.42318(9) 0.0690(5) Uani 1 1 d . . .
HOH H 0.0898(12) 0.294(5) 0.4056(14) 0.101(8) Uiso 1 1 d . . .
C1 C 0.07685(10) 0.2144(5) 0.50192(13) 0.0517(6) Uani 1 1 d . . .
C2 C 0.02744(9) 0.0787(4) 0.52486(11) 0.0512(6) Uani 1 1 d . . .
H2 H 0.0366 0.1088 0.5789 0.061 Uiso 1 1 calc R . .
C3 C 0.09929(10) 0.3566(4) 0.27883(12) 0.0556(6) Uani 1 1 d . . .
H3 H 0.0587 0.2426 0.2571 0.067 Uiso 1 1 calc R . .
C4 C 0.12311(11) 0.4421(5) 0.22661(11) 0.0560(6) Uani 1 1 d . . .
H4 H 0.0989 0.3909 0.1709 0.067 Uiso 1 1 calc R . .
C5 C 0.18360(11) 0.6056(4) 0.25847(11) 0.0544(6) Uani 1 1 d . . .
H5 H 0.2011 0.6669 0.2245 0.065 Uiso 1 1 calc R . .
C6 C 0.21779(10) 0.6772(4) 0.34096(11) 0.0502(6) Uani 1 1 d . . .
H6 H 0.2592 0.7834 0.3637 0.060 Uiso 1 1 calc R . .
C7 C 0.22157(8) 0.6665(4) 0.47836(10) 0.0466(5) Uani 1 1 d . . .
H7 H 0.1998 0.5914 0.5065 0.056 Uiso 1 1 calc R . .
C8 C 0.19001(9) 0.5896(4) 0.39076(10) 0.0422(5) 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
N1 C3 1.336(2) . ?
N1 C8 1.346(2) . ?
O1 C1 1.195(2) . ?
O2 C1 1.311(2) . ?
O2 HOH 1.02(3) . ?
C1 C2 1.489(3) . ?
C2 C2 1.300(3) 5_556 ?
C2 H2 0.9300 . ?
C3 C4 1.368(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(2) . ?
C5 H5 0.9300 . ?
C6 C8 1.398(3) . ?
C6 H6 0.9300 . ?
C7 C7 1.326(3) 7_566 ?
C7 C8 1.458(2) . ?
C7 H7 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 C8 118.07(16) . . ?
C1 O2 HOH 115.4(12) . . ?
O1 C1 O2 124.66(19) . . ?
O1 C1 C2 121.33(19) . . ?
O2 C1 C2 114.01(18) . . ?
C2 C2 C1 125.0(2) 5_556 . ?
C2 C2 H2 117.5 5_556 . ?
C1 C2 H2 117.5 . . ?
N1 C3 C4 123.86(19) . . ?
N1 C3 H3 118.1 . . ?
C4 C3 H3 118.1 . . ?
C3 C4 C5 118.40(18) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 119.14(18) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C8 119.67(18) . . ?
C5 C6 H6 120.2 . . ?
C8 C6 H6 120.2 . . ?
C7 C7 C8 126.1(2) 7_566 . ?
C7 C7 H7 116.9 7_566 . ?
C8 C7 H7 116.9 . . ?
N1 C8 C6 120.84(16) . . ?
N1 C8 C7 115.69(15) . . ?
C6 C8 C7 123.47(17) . . ?

_diffrn_measured_fraction_theta_max 0.815
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.060

# End of CIF ============================================================


# Attachment 'SHELXLEC1.CIF'

data_shelxle
_database_code_depnum_ccdc_archive 'CCDC 704339'

#==========================================================================

_audit_creation_method           SHELXL-97
_audit_creation_date             '20 August 2008'

#==========================================================================

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N2, C5 H6 O4, H2 O'
_chemical_formula_sum            'C17 H18 N2 O5'
_chemical_formula_weight         330.33
_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           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  -C2yc

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

_cell_length_a                   19.841(8)
_cell_length_b                   11.394(5)
_cell_length_c                   14.637(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.423(13)
_cell_angle_gamma                90.00
_cell_volume                     3303(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1272
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      26.30

_exptl_crystal_description       Prism
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   'Multi Scan'
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_T_max  0.965
_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       'ω '
_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            18144
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         28.13
_reflns_number_total             3205
_reflns_number_gt                1958
_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)
;
_computing_publication_material  
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003).
;

_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)+(0.1031P)²+3.0139P] 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     SHELXL
_refine_ls_extinction_coef       0.0022(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3205
_refine_ls_number_parameters     266
_refine_ls_number_restraints     266
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.0748
_refine_ls_wR_factor_ref         0.2293
_refine_ls_wR_factor_gt          0.1954
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.038
_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
O1W O 0.31807(14) -0.7614(3) 0.5434(2) 0.0836(9) Uani 1 1 d . . .
H1W1 H 0.335(2) -0.693(4) 0.544(3) 0.107(16) Uiso 1 1 d . . .
H2W1 H 0.294(3) -0.766(7) 0.489(5) 0.23(4) Uiso 1 1 d . . .
O3 O 0.39007(12) 0.0585(2) 0.6023(2) 0.0936(9) Uani 1 1 d . . .
H1O3 H 0.3674 0.1204 0.5899 0.112 Uiso 1 1 d R . .
O2 O 0.55795(12) -0.2317(2) 0.6638(2) 0.0926(9) Uani 1 1 d . . .
H2O2 H 0.5791 -0.2964 0.6695 0.111 Uiso 1 1 d R . .
O4 O 0.47494(14) 0.1827(2) 0.6101(3) 0.1145(11) Uani 1 1 d . . .
O1 O 0.65789(14) -0.1520(3) 0.6468(3) 0.1258(13) Uani 1 1 d . . .
N1 N 0.35552(11) -0.5225(2) 0.54574(16) 0.0554(7) Uani 1 1 d . . .
C1 C 0.59706(17) -0.1425(3) 0.6522(2) 0.0701(9) Uani 1 1 d . . .
C2 C 0.56236(15) -0.0266(3) 0.6362(2) 0.0618(8) Uani 1 1 d . . .
C3 C 0.49589(15) -0.0224(3) 0.6312(2) 0.0619(8) Uani 1 1 d . . .
H3 H 0.4731 -0.0926 0.6393 0.074 Uiso 1 1 calc R . .
C4 C 0.45429(17) 0.0839(3) 0.6139(2) 0.0674(9) Uani 1 1 d . . .
C5 C 0.60934(19) 0.0749(3) 0.6270(3) 0.0966(13) Uani 1 1 d . . .
H5A H 0.5836 0.1457 0.6176 0.145 Uiso 1 1 calc R . .
H5B H 0.6364 0.0621 0.5756 0.145 Uiso 1 1 calc R . .
H5C H 0.6382 0.0820 0.6817 0.145 Uiso 1 1 calc R . .
C6 C 0.47090(13) -0.5229(3) 0.51097(18) 0.0515(7) Uani 1 1 d . . .
H6 H 0.4680 -0.6044 0.5119 0.062 Uiso 1 1 calc R . .
C7 C 0.41064(13) -0.4576(3) 0.53382(17) 0.0494(7) Uani 1 1 d . . .
C8 C 0.29869(14) -0.4667(3) 0.5670(2) 0.0613(8) Uani 1 1 d . . .
H8 H 0.2602 -0.5114 0.5746 0.074 Uiso 1 1 calc R . .
C9 C 0.29461(16) -0.3477(3) 0.5782(2) 0.0650(9) Uani 1 1 d . . .
H9 H 0.2544 -0.3124 0.5927 0.078 Uiso 1 1 calc R . .
C10 C 0.35092(18) -0.2823(3) 0.5674(2) 0.0730(10) Uani 1 1 d . . .
H10 H 0.3497 -0.2013 0.5750 0.088 Uiso 1 1 calc R . .
C11 C 0.40975(15) -0.3367(3) 0.5451(2) 0.0637(9) Uani 1 1 d . . .
H11 H 0.4486 -0.2928 0.5378 0.076 Uiso 1 1 calc R . .
C12 C 0.4753(2) -0.5667(8) 0.7577(4) 0.056(2) Uani 0.492(10) 1 d PDU . 1
H12 H 0.4787 -0.6379 0.7887 0.067 Uiso 0.50 1 calc PR . 1
C13 C 0.4039(2) -0.5520(8) 0.7735(6) 0.058(2) Uani 0.492(10) 1 d PGDU . 1
N2 N 0.3827(4) -0.4405(7) 0.7977(7) 0.049(2) Uani 0.492(10) 1 d PGU . 1
C14 C 0.3152(4) -0.4206(5) 0.8134(8) 0.053(2) Uani 0.492(10) 1 d PGU . 1
H14 H 0.3011 -0.3461 0.8296 0.064 Uiso 0.492(10) 1 calc PR . 1
C15 C 0.2690(3) -0.5122(8) 0.8050(9) 0.062(3) Uani 0.492(10) 1 d PGU . 1
H15 H 0.2239 -0.4989 0.8155 0.074 Uiso 0.492(10) 1 calc PR . 1
C16 C 0.2902(3) -0.6236(6) 0.7808(7) 0.071(2) Uani 0.492(10) 1 d PGU . 1
H16 H 0.2592 -0.6849 0.7751 0.085 Uiso 0.492(10) 1 calc PR . 1
C17 C 0.3576(4) -0.6435(6) 0.7651(6) 0.060(2) Uani 0.492(10) 1 d PGU . 1
H17 H 0.3718 -0.7181 0.7489 0.072 Uiso 0.492(10) 1 calc PR . 1
C12A C 0.4805(2) -0.4841(8) 0.7545(5) 0.052(2) Uani 0.508(10) 1 d PDU . 2
H12A H 0.4747 -0.4037 0.7468 0.062 Uiso 0.50 1 calc PR . 2
C13A C 0.4105(2) -0.5085(7) 0.7735(6) 0.0480(18) Uani 0.508(10) 1 d PGDU . 2
N2A N 0.3741(4) -0.4175(5) 0.8103(7) 0.059(2) Uani 0.508(10) 1 d PGU . 2
C14A C 0.3070(4) -0.4344(6) 0.8295(8) 0.056(2) Uani 0.508(10) 1 d PGU . 2
H14A H 0.2827 -0.3734 0.8541 0.067 Uiso 0.508(10) 1 calc PR . 2
C15A C 0.2763(3) -0.5423(8) 0.8119(8) 0.058(2) Uani 0.508(10) 1 d PGU . 2
H15A H 0.2314 -0.5536 0.8248 0.070 Uiso 0.508(10) 1 calc PR . 2
C16A C 0.3127(4) -0.6333(6) 0.7752(7) 0.064(2) Uani 0.508(10) 1 d PGU . 2
H16A H 0.2921 -0.7056 0.7634 0.076 Uiso 0.508(10) 1 calc PR . 2
C17A C 0.3797(4) -0.6165(6) 0.7560(5) 0.060(2) Uani 0.508(10) 1 d PGU . 2
H17A H 0.4040 -0.6774 0.7314 0.072 Uiso 0.508(10) 1 calc PR . 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
O1W H1W1 0.84(5) . ?
O1W H2W1 0.90(8) . ?
O3 C4 1.308(4) . ?
O3 H1O3 0.8501 . ?
O2 C1 1.296(4) . ?
O2 H2O2 0.8500 . ?
O4 C4 1.201(4) . ?
O1 C1 1.219(4) . ?
N1 C7 1.340(3) . ?
N1 C8 1.347(4) . ?
C1 C2 1.501(5) . ?
C2 C3 1.317(4) . ?
C2 C5 1.497(5) . ?
C3 C4 1.478(5) . ?
C3 H3 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C6 1.324(5) 5_646 ?
C6 C7 1.464(4) . ?
C6 H6 0.9300 . ?
C7 C11 1.388(4) . ?
C8 C9 1.369(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.360(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C12 1.018(8) 2_656 ?
C12 C13 1.459(2) . ?
C12 H12 0.9300 . ?
C13 N2 1.3900 . ?
C13 C17 1.3900 . ?
N2 C14 1.3900 . ?
C14 C15 1.3900 . ?
C14 H14 0.9300 . ?
C15 C16 1.3900 . ?
C15 H15 0.9300 . ?
C16 C17 1.3900 . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C12A C12A 0.791(8) 2_656 ?
C12A C13A 1.460(2) . ?
C12A H12A 0.9300 . ?
C13A N2A 1.3900 . ?
C13A C17A 1.3900 . ?
N2A C14A 1.3900 . ?
C14A C15A 1.3900 . ?
C14A H14A 0.9300 . ?
C15A C16A 1.3900 . ?
C15A H15A 0.9300 . ?
C16A C17A 1.3900 . ?
C16A H16A 0.9300 . ?
C17A H17A 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
H1W1 O1W H2W1 104(5) . . ?
C4 O3 H1O3 110.0 . . ?
C1 O2 H2O2 113.4 . . ?
C7 N1 C8 118.1(3) . . ?
O1 C1 O2 122.8(3) . . ?
O1 C1 C2 121.0(3) . . ?
O2 C1 C2 115.9(3) . . ?
C3 C2 C5 126.4(3) . . ?
C3 C2 C1 119.3(3) . . ?
C5 C2 C1 114.3(3) . . ?
C2 C3 C4 125.9(3) . . ?
C2 C3 H3 117.1 . . ?
C4 C3 H3 117.1 . . ?
O4 C4 O3 122.3(3) . . ?
O4 C4 C3 126.0(3) . . ?
O3 C4 C3 111.8(3) . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 C6 C7 126.2(4) 5_646 . ?
C6 C6 H6 116.9 5_646 . ?
C7 C6 H6 116.9 . . ?
N1 C7 C11 121.0(3) . . ?
N1 C7 C6 115.7(3) . . ?
C11 C7 C6 123.2(3) . . ?
N1 C8 C9 123.4(3) . . ?
N1 C8 H8 118.3 . . ?
C9 C8 H8 118.3 . . ?
C10 C9 C8 118.3(3) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C7 119.5(3) . . ?
C10 C11 H11 120.3 . . ?
C7 C11 H11 120.3 . . ?
C12 C12 C13 172.4(6) 2_656 . ?
C12 C12 H12 93.8 2_656 . ?
C13 C12 H12 93.8 . . ?
N2 C13 C17 120.0 . . ?
N2 C13 C12 117.2(6) . . ?
C17 C13 C12 122.8(6) . . ?
C13 N2 C14 120.0 . . ?
N2 C14 C15 120.0 . . ?
N2 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C13 120.0 . . ?
C16 C17 H17 120.0 . . ?
C13 C17 H17 120.0 . . ?
C12A C12A C13A 168.9(4) 2_656 . ?
C12A C12A H12A 95.5 2_656 . ?
C13A C12A H12A 95.5 . . ?
N2A C13A C17A 120.0 . . ?
N2A C13A C12A 117.0(5) . . ?
C17A C13A C12A 123.0(5) . . ?
C13A N2A C14A 120.0 . . ?
C15A C14A N2A 120.0 . . ?
C15A C14A H14A 120.0 . . ?
N2A C14A H14A 120.0 . . ?
C14A C15A C16A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C17A C16A C15A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C16A C17A C13A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C13A C17A H17A 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.794
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.045


