# 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

_publ_contact_author_name        'Biao Wu'
_publ_contact_author_email       WUBIAO@LZB.AC.CN

_publ_section_title              
;
A flexible bis(pyridylcarbamate) anion receptor:
binding of infinite double-stranded phosphate, [-sulfate-(H2O)2-]n,
and hydrogen-bridged helical perchlorate chain
;
loop_
_publ_author_name
'Biao Wu'
'Li He'
'Xiaojuan Huang'
'Yanyan Liu'
'Yana Xia'
'Zaiwen Yang'
;
Xiao-Juan Yang
;

# Attachment 'L_anions_R1.cif'

data_LH3PO4
_database_code_depnum_ccdc_archive 'CCDC 722508'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 N4 O12 P2'
_chemical_formula_weight         498.28

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'
P P 0.1023 0.0942 '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                   9.134(4)
_cell_length_b                   20.071(8)
_cell_length_c                   11.292(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.478(8)
_cell_angle_gamma                90.00
_cell_volume                     2069.5(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9125
_exptl_absorpt_correction_T_max  0.9457
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10587
_diffrn_reflns_av_R_equivalents  0.1527
_diffrn_reflns_av_sigmaI/netI    0.2558
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         26.44
_reflns_number_total             4149
_reflns_number_gt                1562
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0476P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0046(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4149
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1648
_refine_ls_R_factor_gt           0.0713
_refine_ls_wR_factor_ref         0.1488
_refine_ls_wR_factor_gt          0.1311
_refine_ls_goodness_of_fit_ref   0.806
_refine_ls_restrained_S_all      0.806
_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
P2 P 0.56413(15) 0.07302(5) 0.12454(13) 0.0330(4) Uani 1 1 d . . .
P1 P 0.05445(15) 0.05827(5) 0.15182(12) 0.0312(4) Uani 1 1 d . . .
O1 O 0.1159(4) 0.17349(15) 0.5572(3) 0.0592(12) Uani 1 1 d . . .
O2 O 0.1274(4) 0.06330(14) 0.5927(3) 0.0491(11) Uani 1 1 d . . .
O3 O 0.3598(4) -0.02512(14) 0.3979(3) 0.0523(11) Uani 1 1 d . . .
O4 O 0.3706(5) -0.13386(16) 0.4410(4) 0.0713(13) Uani 1 1 d . . .
O5 O -0.0726(3) 0.08494(13) 0.2207(3) 0.0490(11) Uani 1 1 d . . .
O6 O 0.0552(4) 0.08747(13) 0.0234(3) 0.0576(13) Uani 1 1 d . . .
H6A H -0.0112 0.0706 -0.0165 0.086 Uiso 1 1 calc R . .
O7 O 0.0588(3) -0.01646(11) 0.1461(3) 0.0363(10) Uani 1 1 d . . .
O8 O 0.1938(3) 0.08870(13) 0.2101(3) 0.0376(9) Uani 1 1 d . . .
H8C H 0.2633 0.0635 0.2007 0.056 Uiso 1 1 calc R . .
O9 O 0.6734(3) 0.03065(13) 0.2011(3) 0.0452(11) Uani 1 1 d . . .
H9A H 0.7529 0.0496 0.2054 0.068 Uiso 1 1 calc R . .
O10 O 0.4242(3) 0.03491(13) 0.1254(3) 0.0433(10) Uani 1 1 d . . .
O11 O 0.5595(4) 0.14334(13) 0.1664(3) 0.0571(13) Uani 1 1 d . . .
O12 O 0.6256(4) 0.07469(13) -0.0031(3) 0.0470(10) Uani 1 1 d . . .
H12B H 0.6071 0.0393 -0.0366 0.070 Uiso 1 1 calc R . .
N1 N -0.1204(5) 0.29323(17) 0.7827(4) 0.0415(13) Uani 1 1 d . . .
H1A H -0.1043 0.3335 0.7603 0.050 Uiso 1 1 calc R . .
N2 N -0.0105(5) 0.12398(17) 0.7055(4) 0.0368(12) Uani 1 1 d . . .
H2A H -0.0293 0.0854 0.7344 0.044 Uiso 1 1 calc R . .
N3 N 0.4946(5) -0.09089(17) 0.2883(4) 0.0487(13) Uani 1 1 d . . .
H3A H 0.5127 -0.0538 0.2535 0.058 Uiso 1 1 calc R . .
N4 N 0.5892(5) -0.26462(18) 0.2357(4) 0.0448(13) Uani 1 1 d . . .
H4A H 0.5663 -0.3034 0.2618 0.054 Uiso 1 1 calc R . .
C1 C -0.0547(5) 0.24426(19) 0.7241(4) 0.0367(14) Uani 1 1 d . . .
H1B H 0.0054 0.2537 0.6611 0.044 Uiso 1 1 calc R . .
C2 C -0.0781(6) 0.1792(2) 0.7593(4) 0.0338(14) Uani 1 1 d . . .
C3 C -0.1693(5) 0.1680(2) 0.8513(4) 0.0346(14) Uani 1 1 d . . .
H3B H -0.1885 0.1245 0.8747 0.041 Uiso 1 1 calc R . .
C4 C -0.2331(6) 0.2201(2) 0.9099(4) 0.0428(15) Uani 1 1 d . . .
H4B H -0.2925 0.2122 0.9741 0.051 Uiso 1 1 calc R . .
C5 C -0.2072(6) 0.2845(2) 0.8714(5) 0.0458(16) Uani 1 1 d . . .
H5A H -0.2507 0.3208 0.9080 0.055 Uiso 1 1 calc R . .
C6 C 0.0802(7) 0.1257(2) 0.6138(5) 0.0457(17) Uani 1 1 d . . .
C7 C 0.2206(6) 0.0558(2) 0.4947(5) 0.0490(16) Uani 1 1 d . . .
H7A H 0.3068 0.0837 0.5040 0.059 Uiso 1 1 calc R . .
H7B H 0.1695 0.0675 0.4213 0.059 Uiso 1 1 calc R . .
C8 C 0.2618(6) -0.0169(2) 0.4954(5) 0.0504(16) Uani 1 1 d . . .
H8A H 0.3104 -0.0288 0.5698 0.060 Uiso 1 1 calc R . .
H8B H 0.1756 -0.0446 0.4844 0.060 Uiso 1 1 calc R . .
C9 C 0.4061(7) -0.0881(2) 0.3809(5) 0.0449(16) Uani 1 1 d . . .
C10 C 0.5274(5) -0.2113(2) 0.2844(5) 0.0413(15) Uani 1 1 d . . .
H10A H 0.4629 -0.2164 0.3461 0.050 Uiso 1 1 calc R . .
C11 C 0.5604(6) -0.1477(2) 0.2421(4) 0.0335(14) Uani 1 1 d . . .
C12 C 0.6594(6) -0.1429(2) 0.1525(5) 0.0388(14) Uani 1 1 d . . .
H12A H 0.6852 -0.1011 0.1242 0.047 Uiso 1 1 calc R . .
C13 C 0.7201(6) -0.1987(2) 0.1046(5) 0.0499(17) Uani 1 1 d . . .
H13A H 0.7850 -0.1951 0.0428 0.060 Uiso 1 1 calc R . .
C14 C 0.6840(7) -0.2607(2) 0.1491(5) 0.0526(18) Uani 1 1 d . . .
H14A H 0.7257 -0.2991 0.1186 0.063 Uiso 1 1 calc R . .


_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
P2 O11 1.490(3) . ?
P2 O10 1.490(3) 1 ?
P2 O10 1.490(3) . ?
P2 O9 1.556(3) . ?
P2 O12 1.560(4) . ?
P1 O7 1.502(3) . ?
P1 O5 1.512(4) . ?
P1 O8 1.543(3) . ?
P1 O6 1.564(3) . ?
O1 C6 1.202(6) . ?
O2 C6 1.348(5) . ?
O2 C7 1.422(6) . ?
O3 C9 1.347(5) . ?
O3 C8 1.446(6) . ?
O4 C9 1.192(6) . ?
O10 O10 0.000(9) 1 ?
N1 C5 1.305(7) . ?
N1 C1 1.335(6) . ?
N2 C6 1.343(7) . ?
N2 C2 1.414(6) . ?
N3 C9 1.340(7) . ?
N3 C11 1.396(6) . ?
N4 C14 1.325(7) . ?
N4 C10 1.335(6) . ?
C1 C2 1.382(6) . ?
C2 C3 1.368(7) . ?
C3 C4 1.374(6) . ?
C4 C5 1.388(6) . ?
C7 C8 1.506(6) . ?
C10 C11 1.398(6) . ?
C11 C12 1.377(7) . ?
C12 C13 1.369(6) . ?
C13 C14 1.384(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
O11 P2 O10 117.0(2) . 1 ?
O11 P2 O10 117.0(2) . . ?
O10 P2 O10 0.0(4) 1 . ?
O11 P2 O9 111.36(18) . . ?
O10 P2 O9 104.71(18) 1 . ?
O10 P2 O9 104.71(18) . . ?
O11 P2 O12 106.7(2) . . ?
O10 P2 O12 110.24(18) 1 . ?
O10 P2 O12 110.24(18) . . ?
O9 P2 O12 106.51(19) . . ?
O7 P1 O5 113.4(2) . . ?
O7 P1 O8 113.03(16) . . ?
O5 P1 O8 106.00(18) . . ?
O7 P1 O6 109.51(18) . . ?
O5 P1 O6 111.50(19) . . ?
O8 P1 O6 102.91(18) . . ?
C6 O2 C7 115.9(4) . . ?
C9 O3 C8 114.7(4) . . ?
O10 O10 P2 0.0(11) 1 . ?
C5 N1 C1 124.8(4) . . ?
C6 N2 C2 126.6(4) . . ?
C9 N3 C11 126.9(4) . . ?
C14 N4 C10 123.2(5) . . ?
N1 C1 C2 118.6(5) . . ?
C3 C2 C1 118.3(5) . . ?
C3 C2 N2 118.6(4) . . ?
C1 C2 N2 123.0(5) . . ?
C2 C3 C4 121.0(4) . . ?
C3 C4 C5 118.7(6) . . ?
N1 C5 C4 118.5(5) . . ?
O1 C6 N2 127.7(5) . . ?
O1 C6 O2 123.7(6) . . ?
N2 C6 O2 108.5(5) . . ?
O2 C7 C8 104.7(4) . . ?
O3 C8 C7 105.5(4) . . ?
O4 C9 N3 126.2(5) . . ?
O4 C9 O3 123.4(6) . . ?
N3 C9 O3 110.4(5) . . ?
N4 C10 C11 119.6(6) . . ?
C12 C11 N3 120.9(4) . . ?
C12 C11 C10 117.8(5) . . ?
N3 C11 C10 121.3(5) . . ?
C13 C12 C11 120.9(5) . . ?
C12 C13 C14 119.3(6) . . ?
N4 C14 C13 119.2(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
C1 H1B O1 0.93 2.25 2.855(7) 122.4 .
C10 H10A O4 0.93 2.16 2.780(7) 123.5 .
O9 H9A O5 0.82 1.75 2.568(4) 175.7 1_655
N1 H1A O5 0.86 1.72 2.584(5) 177.9 4_566
O6 H6A O7 0.82 1.87 2.584(4) 145.7 3
N2 H2A O7 0.86 1.96 2.775(5) 158.7 3_556
O8 H8C O10 0.82 1.81 2.572(5) 153.7 .
N3 H3A O9 0.86 2.33 3.110(5) 151.2 .
O12 H12B O10 0.82 1.81 2.631(4) 173.5 3_655
N4 H4A O11 0.86 1.78 2.561(5) 149.9 2_645
N3 H3A O10 0.86 2.42 3.180(5) 147.6 1
C5 H5A O4 0.93 2.24 3.092(7) 151.3 2_556
C14 H14A O1 0.93 2.55 3.277(8) 135.6 2_645
C3 H3B O12 0.93 2.43 3.143(6) 133.3 1_456
C3 H3B O7 0.93 2.49 3.205(5) 134.3 3_556
C7 H7B O8 0.97 2.44 3.284(6) 145.5 .

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.104

############

data_LH2SO4
_database_code_depnum_ccdc_archive 'CCDC 722509'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 N4 O10 S'
_chemical_formula_weight         436.40

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'
S S 0.1246 0.1234 '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                   6.8550(14)
_cell_length_b                   36.204(7)
_cell_length_c                   7.5513(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.79(3)
_cell_angle_gamma                90.00
_cell_volume                     1873.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9133
_exptl_absorpt_correction_T_max  0.9498
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12433
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         30.83
_reflns_number_total             4911
_reflns_number_gt                3955
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0569P)²+0.7068P] 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         4911
_refine_ls_number_parameters     274
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
S1 S 0.05990(6) 0.124165(11) 0.78737(6) 0.03364(12) Uani 1 1 d . . .
C1 C 0.1749(3) 0.06398(5) 1.3215(2) 0.0382(4) Uani 1 1 d . . .
H1A H 0.1493 0.0862 1.3787 0.046 Uiso 1 1 calc R . .
C2 C 0.2166(3) 0.03248(5) 1.4184(2) 0.0401(4) Uani 1 1 d . . .
H2A H 0.2163 0.0331 1.5415 0.048 Uiso 1 1 calc R . .
C3 C 0.2586(3) 0.00013(5) 1.3301(2) 0.0376(4) Uani 1 1 d . . .
H3A H 0.2878 -0.0211 1.3943 0.045 Uiso 1 1 calc R . .
C4 C 0.2577(2) -0.00105(4) 1.1442(2) 0.0308(3) Uani 1 1 d . . .
C5 C 0.2102(2) 0.03124(4) 1.0523(2) 0.0329(3) Uani 1 1 d . . .
H5A H 0.2051 0.0314 0.9292 0.039 Uiso 1 1 calc R . .
C6 C 0.2940(2) -0.04213(4) 0.8864(2) 0.0317(3) Uani 1 1 d . . .
C7 C 0.3332(3) -0.09171(5) 0.6841(2) 0.0351(4) Uani 1 1 d . . .
H7A H 0.4436 -0.0819 0.6201 0.042 Uiso 1 1 calc R . .
H7B H 0.2143 -0.0840 0.6236 0.042 Uiso 1 1 calc R . .
C8 C 0.3437(2) -0.13310(5) 0.6916(3) 0.0384(4) Uani 1 1 d . . .
H8A H 0.2421 -0.1427 0.7670 0.046 Uiso 1 1 calc R . .
H8B H 0.3256 -0.1434 0.5739 0.046 Uiso 1 1 calc R . .
C9 C 0.5770(3) -0.17948(4) 0.7596(2) 0.0350(4) Uani 1 1 d . . .
C10 C 0.8489(2) -0.21784(4) 0.8754(2) 0.0316(3) Uani 1 1 d . . .
C11 C 1.0376(3) -0.21602(5) 0.9505(2) 0.0364(4) Uani 1 1 d . . .
H11A H 1.0940 -0.1931 0.9739 0.044 Uiso 1 1 calc R . .
C12 C 1.1402(3) -0.24793(5) 0.9898(2) 0.0424(4) Uani 1 1 d . . .
H12A H 1.2642 -0.2466 1.0411 0.051 Uiso 1 1 calc R . .
C13 C 1.0568(3) -0.28150(5) 0.9523(2) 0.0436(4) Uani 1 1 d . . .
H13A H 1.1243 -0.3032 0.9769 0.052 Uiso 1 1 calc R . .
C14 C 0.7696(3) -0.25251(4) 0.8404(2) 0.0366(4) Uani 1 1 d . . .
H14A H 0.6452 -0.2548 0.7908 0.044 Uiso 1 1 calc R . .
N1 N 0.1718(2) 0.06212(4) 1.14446(19) 0.0355(3) Uani 1 1 d . . .
H1B H 0.1437 0.0819 1.0861 0.043 Uiso 1 1 calc R . .
N2 N 0.3042(2) -0.03433(4) 1.06258(18) 0.0374(3) Uani 1 1 d . . .
H2B H 0.3436 -0.0519 1.1310 0.045 Uiso 1 1 calc R . .
N3 N 0.7556(2) -0.18438(4) 0.8398(2) 0.0375(3) Uani 1 1 d . . .
H3B H 0.8168 -0.1647 0.8717 0.045 Uiso 1 1 calc R . .
N4 N 0.8773(2) -0.28280(4) 0.8800(2) 0.0406(3) Uani 1 1 d . . .
H4A H 0.8276 -0.3041 0.8575 0.049 Uiso 1 1 calc R . .
O1 O 0.2536(2) -0.02094(3) 0.76745(16) 0.0423(3) Uani 1 1 d . . .
O2 O 0.3359(2) -0.07824(3) 0.86414(16) 0.0417(3) Uani 1 1 d . . .
O3 O 0.53431(18) -0.14310(3) 0.76234(17) 0.0391(3) Uani 1 1 d . . .
O4 O 0.4756(2) -0.20322(4) 0.6944(2) 0.0517(4) Uani 1 1 d . . .
O5 O 0.0626(2) 0.12534(3) 0.98481(17) 0.0438(3) Uani 1 1 d . . .
O6 O -0.1262(2) 0.13945(4) 0.7225(2) 0.0524(4) Uani 1 1 d . . .
O7 O 0.0892(3) 0.08639(4) 0.7307(2) 0.0692(5) Uani 1 1 d . . .
O8 O 0.2200(2) 0.14834(4) 0.7236(2) 0.0615(4) Uani 1 1 d . . .
O9 O 0.5617(3) 0.18700(5) 0.8361(3) 0.0764(5) Uani 1 1 d D . .
H9B H 0.654(3) 0.1723(7) 0.811(4) 0.080 Uiso 1 1 d D . .
H9A H 0.464(3) 0.1724(7) 0.832(4) 0.080 Uiso 1 1 d D . .
O10 O 0.5551(2) 0.08922(4) 0.7104(2) 0.0476(3) Uani 1 1 d D . .
H10B H 0.643(3) 0.1058(6) 0.721(4) 0.080 Uiso 1 1 d D . .
H10A H 0.440(2) 0.0979(8) 0.714(4) 0.080 Uiso 1 1 d 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
S1 O7 1.4476(14) . ?
S1 O6 1.4685(14) . ?
S1 O8 1.4888(15) . ?
S1 O5 1.4914(14) . ?
C1 N1 1.339(2) . ?
C1 C2 1.383(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.380(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.404(2) . ?
C3 H3A 0.9300 . ?
C4 N2 1.392(2) . ?
C4 C5 1.396(2) . ?
C5 N1 1.345(2) . ?
C5 H5A 0.9300 . ?
C6 O1 1.2102(19) . ?
C6 O2 1.3494(19) . ?
C6 N2 1.361(2) . ?
C7 O2 1.445(2) . ?
C7 C8 1.501(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O3 1.451(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O4 1.206(2) . ?
C9 O3 1.3494(19) . ?
C9 N3 1.370(2) . ?
C10 C14 1.392(2) . ?
C10 N3 1.394(2) . ?
C10 C11 1.407(2) . ?
C11 C12 1.383(2) . ?
C11 H11A 0.9300 . ?
C12 C13 1.371(3) . ?
C12 H12A 0.9300 . ?
C13 N4 1.340(3) . ?
C13 H13A 0.9300 . ?
C14 N4 1.353(2) . ?
C14 H14A 0.9300 . ?
N1 H1B 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3B 0.8600 . ?
N4 H4A 0.8600 . ?
O9 H9B 0.849(10) . ?
O9 H9A 0.852(10) . ?
O10 H10B 0.851(10) . ?
O10 H10A 0.850(10) . ?

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
O7 S1 O6 112.40(10) . . ?
O7 S1 O8 110.73(11) . . ?
O6 S1 O8 108.15(8) . . ?
O7 S1 O5 108.81(8) . . ?
O6 S1 O5 108.75(9) . . ?
O8 S1 O5 107.89(9) . . ?
N1 C1 C2 119.16(16) . . ?
N1 C1 H1A 120.4 . . ?
C2 C1 H1A 120.4 . . ?
C3 C2 C1 119.16(16) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C2 C3 C4 120.73(15) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
N2 C4 C5 123.94(14) . . ?
N2 C4 C3 118.10(14) . . ?
C5 C4 C3 117.96(15) . . ?
N1 C5 C4 119.05(15) . . ?
N1 C5 H5A 120.5 . . ?
C4 C5 H5A 120.5 . . ?
O1 C6 O2 124.64(15) . . ?
O1 C6 N2 127.03(15) . . ?
O2 C6 N2 108.33(13) . . ?
O2 C7 C8 107.55(14) . . ?
O2 C7 H7A 110.2 . . ?
C8 C7 H7A 110.2 . . ?
O2 C7 H7B 110.2 . . ?
C8 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
O3 C8 C7 107.79(13) . . ?
O3 C8 H8A 110.1 . . ?
C7 C8 H8A 110.1 . . ?
O3 C8 H8B 110.1 . . ?
C7 C8 H8B 110.1 . . ?
H8A C8 H8B 108.5 . . ?
O4 C9 O3 125.31(15) . . ?
O4 C9 N3 126.49(16) . . ?
O3 C9 N3 108.18(13) . . ?
C14 C10 N3 124.76(15) . . ?
C14 C10 C11 118.25(15) . . ?
N3 C10 C11 116.99(14) . . ?
C12 C11 C10 120.65(16) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C13 C12 C11 119.12(17) . . ?
C13 C12 H12A 120.4 . . ?
C11 C12 H12A 120.4 . . ?
N4 C13 C12 119.57(16) . . ?
N4 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
N4 C14 C10 118.59(16) . . ?
N4 C14 H14A 120.7 . . ?
C10 C14 H14A 120.7 . . ?
C1 N1 C5 123.92(14) . . ?
C1 N1 H1B 118.0 . . ?
C5 N1 H1B 118.0 . . ?
C6 N2 C4 127.10(14) . . ?
C6 N2 H2B 116.4 . . ?
C4 N2 H2B 116.4 . . ?
C9 N3 C10 127.03(14) . . ?
C9 N3 H3B 116.5 . . ?
C10 N3 H3B 116.5 . . ?
C13 N4 C14 123.83(16) . . ?
C13 N4 H4A 118.1 . . ?
C14 N4 H4A 118.1 . . ?
C6 O2 C7 116.39(13) . . ?
C9 O3 C8 115.61(12) . . ?
H9B O9 H9A 101(3) . . ?
H10B O10 H10A 113(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
N1 C1 C2 C3 1.6(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 N2 179.05(17) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
N2 C4 C5 N1 -178.55(16) . . . . ?
C3 C4 C5 N1 1.5(2) . . . . ?
O2 C7 C8 O3 -67.02(18) . . . . ?
C14 C10 C11 C12 -0.6(3) . . . . ?
N3 C10 C11 C12 179.99(16) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C11 C12 C13 N4 -0.6(3) . . . . ?
N3 C10 C14 N4 179.31(16) . . . . ?
C11 C10 C14 N4 0.0(2) . . . . ?
C2 C1 N1 C5 -1.1(3) . . . . ?
C4 C5 N1 C1 -0.5(3) . . . . ?
O1 C6 N2 C4 4.7(3) . . . . ?
O2 C6 N2 C4 -174.95(16) . . . . ?
C5 C4 N2 C6 -6.6(3) . . . . ?
C3 C4 N2 C6 173.37(16) . . . . ?
O4 C9 N3 C10 -5.8(3) . . . . ?
O3 C9 N3 C10 175.55(16) . . . . ?
C14 C10 N3 C9 -2.8(3) . . . . ?
C11 C10 N3 C9 176.56(17) . . . . ?
C12 C13 N4 C14 0.0(3) . . . . ?
C10 C14 N4 C13 0.4(3) . . . . ?
O1 C6 O2 C7 0.6(2) . . . . ?
N2 C6 O2 C7 -179.71(14) . . . . ?
C8 C7 O2 C6 -169.00(14) . . . . ?
O4 C9 O3 C8 4.8(3) . . . . ?
N3 C9 O3 C8 -176.52(15) . . . . ?
C7 C8 O3 C9 -172.85(15) . . . . ?

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
N1 H1B O5 0.86 1.83 2.6883(19) 172.7 .
N2 H2B O10 0.86 1.93 2.788(2) 176.4 3_657
N3 H3B O5 0.86 1.97 2.7981(19) 162.8 3_657
N4 H4A O8 0.86 1.85 2.694(2) 165.1 2_646
C2 H2A O7 0.93 2.56 3.192(2) 125.5 1_556
C5 H5A O1 0.93 2.28 2.882(2) 121.8 .
C7 H7A O10 0.97 2.51 3.087(2) 118.0 3_656
C12 H12A O4 0.93 2.59 3.271(2) 130.9 4_656
C13 H13A O6 0.93 2.56 3.190(2) 125.0 2_646
C14 H14A O4 0.93 2.31 2.898(2) 120.6 .
O10 H10B O6 0.851(10) 1.999(11) 2.843(2) 171(3) 1_655
O10 H10A O8 0.850(10) 2.371(17) 3.143(2) 151(3) .
O10 H10A O7 0.850(10) 2.446(18) 3.201(3) 149(3) .
O9 H9B O6 0.849(10) 2.041(11) 2.886(3) 173(3) 1_655
O9 H9A O8 0.852(10) 2.048(15) 2.848(2) 156(3) .

_diffrn_measured_fraction_theta_max 0.835
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.051

#################

data_LHClO4
_database_code_depnum_ccdc_archive 'CCDC 722510'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Cl2 N4 O12'
_chemical_formula_weight         503.21

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   C2/c

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                   34.633(14)
_cell_length_b                   7.993(3)
_cell_length_c                   14.308(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.437(11)
_cell_angle_gamma                90.00
_cell_volume                     3918(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2064
_exptl_absorpt_coefficient_mu    0.407
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8672
_exptl_absorpt_correction_T_max  0.9193
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12860
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         31.11
_reflns_number_total             5477
_reflns_number_gt                3013
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.1090P)²+4.9507P] 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         5477
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.2228
_refine_ls_wR_factor_gt          0.1857
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.29631(10) 0.1287(5) -0.0729(3) 0.0486(8) Uani 1 1 d . . .
H1A H 0.3187 0.1781 -0.0894 0.058 Uiso 1 1 calc R . .
C2 C 0.26223(10) 0.1342(5) -0.1325(3) 0.0499(9) Uani 1 1 d . . .
H2A H 0.2612 0.1863 -0.1910 0.060 Uiso 1 1 calc R . .
C3 C 0.22938(10) 0.0636(5) -0.1072(2) 0.0463(8) Uani 1 1 d . . .
H3B H 0.2060 0.0682 -0.1483 0.056 Uiso 1 1 calc R . .
C4 C 0.23093(9) -0.0148(4) -0.0204(2) 0.0386(7) Uani 1 1 d . . .
C5 C 0.26641(9) -0.0203(5) 0.0380(2) 0.0447(8) Uani 1 1 d . . .
H5A H 0.2687 -0.0734 0.0964 0.054 Uiso 1 1 calc R . .
C6 C 0.19390(9) -0.1640(4) 0.0854(2) 0.0422(8) Uani 1 1 d . . .
C7 C 0.14788(10) -0.2962(5) 0.1654(3) 0.0489(9) Uani 1 1 d . . .
H7A H 0.1577 -0.2275 0.2196 0.059 Uiso 1 1 calc R . .
H7B H 0.1589 -0.4074 0.1751 0.059 Uiso 1 1 calc R . .
C8 C 0.10443(10) -0.3039(5) 0.1527(3) 0.0461(8) Uani 1 1 d . . .
H8A H 0.0943 -0.3600 0.0941 0.055 Uiso 1 1 calc R . .
H8B H 0.0955 -0.3630 0.2048 0.055 Uiso 1 1 calc R . .
C9 C 0.05473(9) -0.1030(4) 0.1358(2) 0.0428(8) Uani 1 1 d . . .
C10 C 0.01502(9) 0.1515(4) 0.1276(2) 0.0412(7) Uani 1 1 d . . .
C11 C 0.01597(10) 0.3258(5) 0.1248(3) 0.0507(9) Uani 1 1 d . . .
H11A H 0.0397 0.3814 0.1283 0.061 Uiso 1 1 calc R . .
C12 C -0.01788(11) 0.4145(5) 0.1169(3) 0.0579(10) Uani 1 1 d . . .
H12A H -0.0172 0.5307 0.1154 0.069 Uiso 1 1 calc R . .
C13 C -0.05261(11) 0.3345(5) 0.1112(3) 0.0587(10) Uani 1 1 d . . .
H13A H -0.0759 0.3943 0.1057 0.070 Uiso 1 1 calc R . .
C14 C -0.02065(9) 0.0748(5) 0.1214(3) 0.0486(8) Uani 1 1 d . . .
H14A H -0.0225 -0.0412 0.1225 0.058 Uiso 1 1 calc R . .
N1 N 0.29735(8) 0.0520(4) 0.0092(2) 0.0471(7) Uani 1 1 d . . .
H1B H 0.3193 0.0484 0.0462 0.056 Uiso 1 1 calc R . .
N2 N -0.05258(8) 0.1695(4) 0.1138(2) 0.0559(8) Uani 1 1 d . . .
H2B H -0.0747 0.1196 0.1104 0.067 Uiso 1 1 calc R . .
N3 N 0.19747(7) -0.0844(4) 0.0040(2) 0.0453(7) Uani 1 1 d . . .
H3A H 0.1767 -0.0764 -0.0369 0.054 Uiso 1 1 calc R . .
N4 N 0.04971(8) 0.0655(4) 0.1384(2) 0.0507(8) Uani 1 1 d . . .
H4A H 0.0706 0.1249 0.1478 0.061 Uiso 1 1 calc R . .
O1 O 0.21904(7) -0.1811(4) 0.15123(19) 0.0642(8) Uani 1 1 d . . .
O2 O 0.15797(7) -0.2240(3) 0.08040(17) 0.0483(6) Uani 1 1 d . . .
O3 O 0.09227(7) -0.1330(3) 0.1506(2) 0.0520(6) Uani 1 1 d . . .
O4 O 0.02947(7) -0.2039(4) 0.1218(2) 0.0652(8) Uani 1 1 d . . .
O5 O 0.17113(16) 0.1591(8) 0.2349(4) 0.176(3) Uani 1 1 d . . .
O6 O 0.16442(18) 0.3896(6) 0.3156(4) 0.174(3) Uani 1 1 d . . .
O7 O 0.13300(8) 0.1479(5) 0.3467(2) 0.0885(12) Uani 1 1 d . . .
O8 O 0.11382(9) 0.3007(4) 0.2120(2) 0.0781(10) Uani 1 1 d . . .
O9 O 0.10660(14) 0.6233(5) 0.4938(3) 0.1088(14) Uani 1 1 d . . .
O10 O 0.14204(10) 0.7566(5) 0.3930(3) 0.0921(12) Uani 1 1 d . . .
O11 O 0.07509(9) 0.7517(4) 0.3586(2) 0.0785(10) Uani 1 1 d . . .
O12 O 0.10540(11) 0.9086(4) 0.4828(3) 0.0880(11) Uani 1 1 d . . .
Cl2 Cl 0.10646(3) 0.75763(11) 0.43271(6) 0.0476(3) Uani 1 1 d . . .
Cl1 Cl 0.14530(2) 0.25275(11) 0.27950(7) 0.0475(3) 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 N1 1.320(5) . ?
C1 C2 1.352(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.366(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.386(5) . ?
C3 H3B 0.9300 . ?
C4 N3 1.376(4) . ?
C4 C5 1.382(4) . ?
C5 N1 1.335(4) . ?
C5 H5A 0.9300 . ?
C6 O1 1.193(4) . ?
C6 O2 1.326(4) . ?
C6 N3 1.348(4) . ?
C7 O2 1.435(4) . ?
C7 C8 1.490(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O3 1.429(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O4 1.185(4) . ?
C9 O3 1.308(4) . ?
C9 N4 1.359(5) . ?
C10 C14 1.370(4) . ?
C10 N4 1.373(4) . ?
C10 C11 1.394(5) . ?
C11 C12 1.361(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.354(5) . ?
C12 H12A 0.9300 . ?
C13 N2 1.319(6) . ?
C13 H13A 0.9300 . ?
C14 N2 1.331(4) . ?
C14 H14A 0.9300 . ?
N1 H1B 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3A 0.8600 . ?
N4 H4A 0.8600 . ?
O5 Cl1 1.391(5) . ?
O6 Cl1 1.342(4) . ?
O7 Cl1 1.389(3) . ?
O8 Cl1 1.399(3) . ?
O9 Cl2 1.384(4) . ?
O10 Cl2 1.430(3) . ?
O11 Cl2 1.404(3) . ?
O12 Cl2 1.407(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
N1 C1 C2 119.0(3) . . ?
N1 C1 H1A 120.5 . . ?
C2 C1 H1A 120.5 . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 H2A 119.9 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3B 120.0 . . ?
C4 C3 H3B 120.0 . . ?
N3 C4 C5 122.8(3) . . ?
N3 C4 C3 119.1(3) . . ?
C5 C4 C3 118.1(3) . . ?
N1 C5 C4 118.8(3) . . ?
N1 C5 H5A 120.6 . . ?
C4 C5 H5A 120.6 . . ?
O1 C6 O2 124.8(3) . . ?
O1 C6 N3 126.0(3) . . ?
O2 C6 N3 109.2(3) . . ?
O2 C7 C8 106.3(3) . . ?
O2 C7 H7A 110.5 . . ?
C8 C7 H7A 110.5 . . ?
O2 C7 H7B 110.5 . . ?
C8 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
O3 C8 C7 104.6(3) . . ?
O3 C8 H8A 110.8 . . ?
C7 C8 H8A 110.8 . . ?
O3 C8 H8B 110.8 . . ?
C7 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
O4 C9 O3 126.5(3) . . ?
O4 C9 N4 125.8(3) . . ?
O3 C9 N4 107.8(3) . . ?
C14 C10 N4 123.3(3) . . ?
C14 C10 C11 118.0(3) . . ?
N4 C10 C11 118.7(3) . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
N2 C13 C12 118.2(3) . . ?
N2 C13 H13A 120.9 . . ?
C12 C13 H13A 120.9 . . ?
N2 C14 C10 118.8(3) . . ?
N2 C14 H14A 120.6 . . ?
C10 C14 H14A 120.6 . . ?
C1 N1 C5 123.9(3) . . ?
C1 N1 H1B 118.1 . . ?
C5 N1 H1B 118.1 . . ?
C13 N2 C14 124.6(3) . . ?
C13 N2 H2B 117.7 . . ?
C14 N2 H2B 117.7 . . ?
C6 N3 C4 126.7(3) . . ?
C6 N3 H3A 116.7 . . ?
C4 N3 H3A 116.7 . . ?
C9 N4 C10 127.3(3) . . ?
C9 N4 H4A 116.3 . . ?
C10 N4 H4A 116.3 . . ?
C6 O2 C7 116.3(3) . . ?
C9 O3 C8 117.5(3) . . ?
O9 Cl2 O11 112.4(2) . . ?
O9 Cl2 O12 110.0(3) . . ?
O11 Cl2 O12 109.8(2) . . ?
O9 Cl2 O10 108.8(3) . . ?
O11 Cl2 O10 108.4(2) . . ?
O12 Cl2 O10 107.2(2) . . ?
O6 Cl1 O7 114.2(3) . . ?
O6 Cl1 O5 107.5(5) . . ?
O7 Cl1 O5 106.0(3) . . ?
O6 Cl1 O8 109.4(3) . . ?
O7 Cl1 O8 110.85(19) . . ?
O5 Cl1 O8 108.6(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
N1 C1 C2 C3 1.0(6) . . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
C2 C3 C4 N3 179.7(3) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
N3 C4 C5 N1 -179.3(3) . . . . ?
C3 C4 C5 N1 1.0(5) . . . . ?
O2 C7 C8 O3 -66.9(4) . . . . ?
C14 C10 C11 C12 0.6(5) . . . . ?
N4 C10 C11 C12 -178.1(4) . . . . ?
C10 C11 C12 C13 -0.4(6) . . . . ?
C11 C12 C13 N2 0.2(6) . . . . ?
N4 C10 C14 N2 178.0(3) . . . . ?
C11 C10 C14 N2 -0.6(5) . . . . ?
C2 C1 N1 C5 -0.7(6) . . . . ?
C4 C5 N1 C1 -0.4(5) . . . . ?
C12 C13 N2 C14 -0.2(6) . . . . ?
C10 C14 N2 C13 0.4(6) . . . . ?
O1 C6 N3 C4 3.1(6) . . . . ?
O2 C6 N3 C4 -175.6(3) . . . . ?
C5 C4 N3 C6 0.7(5) . . . . ?
C3 C4 N3 C6 -179.6(3) . . . . ?
O4 C9 N4 C10 1.4(6) . . . . ?
O3 C9 N4 C10 -179.0(3) . . . . ?
C14 C10 N4 C9 6.7(6) . . . . ?
C11 C10 N4 C9 -174.7(4) . . . . ?
O1 C6 O2 C7 8.0(5) . . . . ?
N3 C6 O2 C7 -173.2(3) . . . . ?
C8 C7 O2 C6 162.4(3) . . . . ?
O4 C9 O3 C8 -1.6(6) . . . . ?
N4 C9 O3 C8 178.9(3) . . . . ?
C7 C8 O3 C9 177.0(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
N3 H3A O7 0.86 2.16 2.971(4) 158.0 6
N4 H4A O8 0.86 2.16 2.982(4) 160.4 .
C1 H1A O5 0.93 2.52 3.208(6) 130.6 7
C2 H2A O1 0.93 2.50 3.255(5) 138.2 6
C5 H5A O1 0.93 2.17 2.783(5) 122.5 .
C7 H7B O6 0.97 2.57 3.300(6) 132.3 1_545
C5 H5A O6 0.93 2.49 3.028(5) 117.4 4_545
C8 H8B O11 0.97 2.58 3.284(5) 129.9 1_545
C13 H13A O9 0.93 2.46 3.203(5) 136.6 2
C14 H14A O4 0.93 2.22 2.824(5) 121.7 .
C14 H14A O11 0.93 2.50 3.235(5) 135.6 2_545
N1 H1B O6 0.86 2.35 2.958(5) 128.2 4_545
N1 H1B O10 0.86 2.23 2.859(4) 129.8 4_545
N2 H2B O7 0.86 2.20 2.927(4) 141.5 2
N2 H2B O12 0.86 2.31 2.978(5) 134.6 2_545

_diffrn_measured_fraction_theta_max 0.867
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.845
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.073

######

data_LHCl
_database_code_depnum_ccdc_archive 'CCDC 722511'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Cl2 N4 O4'
_chemical_formula_weight         375.21

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   C2/c

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                   21.659(4)
_cell_length_b                   4.8742(10)
_cell_length_c                   17.943(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.40(3)
_cell_angle_gamma                90.00
_cell_volume                     1633.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.425
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8586
_exptl_absorpt_correction_T_max  0.9198
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5186
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         31.10
_reflns_number_total             2264
_reflns_number_gt                1985
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0579P)²+0.4647P] 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         2264
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0985
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
Cl Cl 0.189373(16) 0.78137(7) 0.34069(2) 0.04219(12) Uani 1 1 d . . .
C1 C 0.33282(7) 1.2611(3) 0.50443(10) 0.0441(3) Uani 1 1 d . . .
H1A H 0.3188 1.3424 0.5404 0.053 Uiso 1 1 calc R . .
C2 C 0.38207(7) 1.0514(3) 0.53403(9) 0.0430(3) Uani 1 1 d . . .
H2A H 0.4010 0.9882 0.5903 0.052 Uiso 1 1 calc R . .
C3 C 0.40378(7) 0.9331(3) 0.48043(8) 0.0374(3) Uani 1 1 d . . .
H3A H 0.4375 0.7927 0.5008 0.045 Uiso 1 1 calc R . .
C4 C 0.37424(6) 1.0280(2) 0.39554(8) 0.0320(2) Uani 1 1 d . . .
C5 C 0.32352(6) 1.2370(2) 0.36803(9) 0.0367(3) Uani 1 1 d . . .
H5A H 0.3022 1.3009 0.3115 0.044 Uiso 1 1 calc R . .
C6 C 0.43809(6) 0.7223(2) 0.34888(8) 0.0318(2) Uani 1 1 d . . .
C7 C 0.49755(6) 0.4870(2) 0.28997(8) 0.0335(2) Uani 1 1 d . . .
H7A H 0.4752 0.3188 0.2935 0.040 Uiso 1 1 calc R . .
H7B H 0.5450 0.4988 0.3406 0.040 Uiso 1 1 calc R . .
N1 N 0.30546(5) 1.3459(2) 0.42261(8) 0.0393(2) Uani 1 1 d . . .
H1B H 0.2747 1.4772 0.4044 0.047 Uiso 1 1 calc R . .
N2 N 0.39263(6) 0.9350(2) 0.33575(7) 0.0370(2) Uani 1 1 d . . .
H2B H 0.3739 1.0181 0.2868 0.044 Uiso 1 1 calc R . .
O1 O 0.46023(6) 0.55799(19) 0.40698(6) 0.0460(2) Uani 1 1 d . . .
O2 O 0.45501(5) 0.72175(16) 0.28636(6) 0.0352(2) 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 N1 1.341(2) . ?
C1 C2 1.375(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.3917(17) . ?
C2 H2A 0.9300 . ?
C3 C4 1.3989(17) . ?
C3 H3A 0.9300 . ?
C4 C5 1.3929(16) . ?
C4 N2 1.3955(15) . ?
C5 N1 1.3347(17) . ?
C5 H5A 0.9300 . ?
C6 O1 1.2052(14) . ?
C6 O2 1.3449(15) . ?
C6 N2 1.3656(15) . ?
C7 O2 1.4498(13) . ?
C7 C7 1.491(2) 2_655 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N1 H1B 0.8600 . ?
N2 H2B 0.8600 . ?

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
N1 C1 C2 118.61(12) . . ?
N1 C1 H1A 120.7 . . ?
C2 C1 H1A 120.7 . . ?
C1 C2 C3 120.56(13) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C2 C3 C4 119.15(12) . . ?
C2 C3 H3A 120.4 . . ?
C4 C3 H3A 120.4 . . ?
C5 C4 N2 116.48(11) . . ?
C5 C4 C3 118.16(11) . . ?
N2 C4 C3 125.34(11) . . ?
N1 C5 C4 120.15(12) . . ?
N1 C5 H5A 119.9 . . ?
C4 C5 H5A 119.9 . . ?
O1 C6 O2 124.27(10) . . ?
O1 C6 N2 126.18(11) . . ?
O2 C6 N2 109.55(10) . . ?
O2 C7 C7 108.06(8) . 2_655 ?
O2 C7 H7A 110.1 . . ?
C7 C7 H7A 110.1 2_655 . ?
O2 C7 H7B 110.1 . . ?
C7 C7 H7B 110.1 2_655 . ?
H7A C7 H7B 108.4 . . ?
C5 N1 C1 123.34(11) . . ?
C5 N1 H1B 118.3 . . ?
C1 N1 H1B 118.3 . . ?
C6 N2 C4 125.11(10) . . ?
C6 N2 H2B 117.4 . . ?
C4 N2 H2B 117.4 . . ?
C6 O2 C7 113.55(9) . . ?

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
N1 C1 C2 C3 1.0(2) . . . . ?
C1 C2 C3 C4 -0.73(19) . . . . ?
C2 C3 C4 C5 -0.53(18) . . . . ?
C2 C3 C4 N2 177.80(11) . . . . ?
N2 C4 C5 N1 -176.93(11) . . . . ?
C3 C4 C5 N1 1.54(17) . . . . ?
C4 C5 N1 C1 -1.35(18) . . . . ?
C2 C1 N1 C5 0.06(19) . . . . ?
O1 C6 N2 C4 12.2(2) . . . . ?
O2 C6 N2 C4 -167.88(10) . . . . ?
C5 C4 N2 C6 -176.18(11) . . . . ?
C3 C4 N2 C6 5.47(19) . . . . ?
O1 C6 O2 C7 5.65(17) . . . . ?
N2 C6 O2 C7 -174.26(10) . . . . ?
C7 C7 O2 C6 170.96(10) 2_655 . . . ?

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
N1 H1B Cl 0.86 2.19 3.0408(13) 172.0 1_565
N2 H2B Cl 0.86 2.36 3.2151(14) 170.9 4
C3 H3A O1 0.93 2.29 2.8643(16) 119.9 .
C5 H5A Cl 0.93 2.83 3.6182(16) 143.4 4
C1 H1A Cl 0.93 2.89 3.7787(15) 161.4 7_576

_diffrn_measured_fraction_theta_max 0.865
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.071

##############

data_LHBr
_database_code_depnum_ccdc_archive 'CCDC 722512'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Br2 N4 O4'
_chemical_formula_weight         464.13

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'
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   C2/c

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                   21.881(4)
_cell_length_b                   4.9052(10)
_cell_length_c                   18.337(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.75(3)
_cell_angle_gamma                90.00
_cell_volume                     1708.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    4.771
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.2938
_exptl_absorpt_correction_T_max  0.4488
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4664
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0593
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       18
_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         2.14
_diffrn_reflns_theta_max         28.13
_reflns_number_total             1929
_reflns_number_gt                1480
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0579P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1929
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_restrained_S_all      0.924
_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
Br Br 0.189590(18) 0.78476(7) 0.341152(19) 0.03975(15) Uani 1 1 d . . .
C1 C 0.3365(2) 1.2416(6) 0.5050(2) 0.0425(9) Uani 1 1 d . . .
H1A H 0.3216 1.3167 0.5401 0.051 Uiso 1 1 calc R . .
C2 C 0.38494(18) 1.0355(7) 0.53267(19) 0.0407(8) Uani 1 1 d . . .
H2A H 0.4029 0.9694 0.5871 0.049 Uiso 1 1 calc R . .
C3 C 0.40760(17) 0.9237(7) 0.48091(17) 0.0353(7) Uani 1 1 d . . .
H3A H 0.4410 0.7850 0.5002 0.042 Uiso 1 1 calc R . .
C4 C 0.37943(16) 1.0234(6) 0.39924(18) 0.0299(7) Uani 1 1 d . . .
C5 C 0.33001(18) 1.2294(6) 0.3732(2) 0.0339(7) Uani 1 1 d . . .
H5A H 0.3100 1.2961 0.3187 0.041 Uiso 1 1 calc R . .
C6 C 0.44290(18) 0.7238(6) 0.35228(18) 0.0294(7) Uani 1 1 d . . .
C7 C 0.49930(17) 0.4951(6) 0.29007(18) 0.0322(7) Uani 1 1 d . . .
H7A H 0.4782 0.3277 0.2953 0.039 Uiso 1 1 calc R . .
H7B H 0.5468 0.5072 0.3373 0.039 Uiso 1 1 calc R . .
N1 N 0.31090(15) 1.3333(5) 0.42633(17) 0.0386(6) Uani 1 1 d . . .
H1B H 0.2809 1.4646 0.4093 0.046 Uiso 1 1 calc R . .
N2 N 0.39824(14) 0.9341(5) 0.34073(15) 0.0348(6) Uani 1 1 d . . .
H2B H 0.3801 1.0188 0.2935 0.042 Uiso 1 1 calc R . .
O1 O 0.46466(12) 0.5594(4) 0.40765(12) 0.0431(6) Uani 1 1 d . . .
O2 O 0.45854(13) 0.7265(4) 0.28970(13) 0.0334(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
C1 N1 1.340(4) . ?
C1 C2 1.368(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.384(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.395(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.381(4) . ?
C4 N2 1.397(3) . ?
C5 N1 1.337(4) . ?
C5 H5A 0.9300 . ?
C6 O1 1.195(3) 1 ?
C6 O1 1.195(3) . ?
C6 O2 1.351(3) . ?
C6 N2 1.363(4) . ?
C7 O2 1.441(3) . ?
C7 C7 1.485(5) 2_655 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N1 H1B 0.8600 . ?
N2 H2B 0.8600 . ?
O1 O1 0.000(5) 1 ?

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
N1 C1 C2 118.7(3) . . ?
N1 C1 H1A 120.7 . . ?
C2 C1 H1A 120.7 . . ?
C1 C2 C3 121.0(3) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 H2A 119.5 . . ?
C2 C3 C4 118.7(3) . . ?
C2 C3 H3A 120.7 . . ?
C4 C3 H3A 120.7 . . ?
C5 C4 C3 118.7(3) . . ?
C5 C4 N2 116.3(3) . . ?
C3 C4 N2 125.0(3) . . ?
N1 C5 C4 120.1(3) . . ?
N1 C5 H5A 119.9 . . ?
C4 C5 H5A 119.9 . . ?
O1 C6 O1 0.0(3) 1 . ?
O1 C6 O2 124.5(3) 1 . ?
O1 C6 O2 124.5(3) . . ?
O1 C6 N2 126.5(3) 1 . ?
O1 C6 N2 126.5(3) . . ?
O2 C6 N2 109.0(2) . . ?
O2 C7 C7 108.2(2) . 2_655 ?
O2 C7 H7A 110.1 . . ?
C7 C7 H7A 110.1 2_655 . ?
O2 C7 H7B 110.1 . . ?
C7 C7 H7B 110.1 2_655 . ?
H7A C7 H7B 108.4 . . ?
C5 N1 C1 122.8(3) . . ?
C5 N1 H1B 118.6 . . ?
C1 N1 H1B 118.6 . . ?
C6 N2 C4 125.4(2) . . ?
C6 N2 H2B 117.3 . . ?
C4 N2 H2B 117.3 . . ?
O1 O1 C6 0(10) 1 . ?
C6 O2 C7 113.9(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
N1 C1 C2 C3 0.3(5) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C2 C3 C4 N2 178.7(3) . . . . ?
C3 C4 C5 N1 1.2(5) . . . . ?
N2 C4 C5 N1 -177.7(3) . . . . ?
C4 C5 N1 C1 -1.7(5) . . . . ?
C2 C1 N1 C5 0.9(5) . . . . ?
O1 C6 N2 C4 11.7(6) 1 . . . ?
O1 C6 N2 C4 11.7(6) . . . . ?
O2 C6 N2 C4 -169.1(3) . . . . ?
C5 C4 N2 C6 -176.2(3) . . . . ?
C3 C4 N2 C6 5.0(5) . . . . ?
O2 C6 O1 O1 0.0(12) . . . 1 ?
N2 C6 O1 O1 0.0(12) . . . 1 ?
O1 C6 O2 C7 5.7(5) 1 . . . ?
O1 C6 O2 C7 5.7(5) . . . . ?
N2 C6 O2 C7 -173.5(3) . . . . ?
C7 C7 O2 C6 169.1(3) 2_655 . . . ?

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
N1 H1B Br 0.86 2.35 3.205(3) 170.5 1_565
N2 H2B Br 0.86 2.53 3.378(3) 170.6 4
C3 H3A O1 0.93 2.29 2.867(4) 119.7 1
C3 H3A O1 0.93 2.29 2.867(4) 119.7 .
C5 H5A Br 0.93 2.94 3.746(3) 146.5 4

_diffrn_measured_fraction_theta_max 0.919
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.579
_refine_diff_density_min         -1.043
_refine_diff_density_rms         0.115

##############END


