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

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Jubaraj Baruah'
_publ_contact_author_address     
;
Department of Chemistry
Indian Institute of Technology
IIT-Guwahati
Guwahati
assam
781039
INDIA
;

_publ_contact_author_email       JUBA@IITG.ERNET.IN

_publ_section_title              
;
Solvent induced symmetry non-equivalence in crystal
lattice
;
loop_
_publ_author_name
'Jubaraj Baruah'
'Nilotpal Barooah'

data_npgi_0m
_database_code_depnum_ccdc_archive 'CCDC 614261'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 N3 O9'
_chemical_formula_weight         455.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   4.94520(10)
_cell_length_b                   32.4040(8)
_cell_length_c                   12.4720(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.869(3)
_cell_angle_gamma                90.00
_cell_volume                     1988.09(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needles
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11690
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.14
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3738
_reflns_number_gt                2297
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0604P)^2^+0.2265P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3738
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
O1 O 0.6231(4) 0.44149(5) 0.69632(13) 0.0612(5) Uani 1 1 d . . .
O6 O 0.4054(4) 0.62627(5) 1.05696(13) 0.0634(5) Uani 1 1 d . . .
O2 O -0.0240(4) 0.37098(5) 0.49024(15) 0.0765(6) Uani 1 1 d . . .
O5 O -0.1478(4) 0.55559(5) 0.81082(15) 0.0687(5) Uani 1 1 d . . .
C14 C 0.4263(4) 0.51826(5) 0.98632(15) 0.0377(5) Uani 1 1 d . . .
C6 C -0.0523(5) 0.44355(6) 0.47730(17) 0.0467(6) Uani 1 1 d . . .
C5 C 0.0588(5) 0.48114(6) 0.51902(16) 0.0417(5) Uani 1 1 d . . .
C4 C 0.2864(5) 0.48182(6) 0.59688(16) 0.0443(5) Uani 1 1 d . . .
C15 C 0.5082(5) 0.55548(6) 1.03887(16) 0.0414(5) Uani 1 1 d . . .
C13 C 0.2004(5) 0.51672(6) 0.90813(16) 0.0419(5) Uani 1 1 d . . .
C16 C 0.3497(5) 0.59336(6) 1.01352(17) 0.0457(6) Uani 1 1 d . . .
C3 C 0.4160(5) 0.44281(7) 0.63482(17) 0.0480(6) Uani 1 1 d . . .
C7 C 0.0660(5) 0.40437(7) 0.51971(18) 0.0536(6) Uani 1 1 d . . .
C1 C 0.2002(5) 0.34265(7) 0.69382(19) 0.0517(6) Uani 1 1 d . . .
C12 C 0.0445(5) 0.55469(6) 0.87920(18) 0.0478(6) Uani 1 1 d . . .
C2 C 0.4011(6) 0.36666(8) 0.6368(3) 0.0588(7) Uani 1 1 d . . .
C11 C -0.0309(6) 0.62817(7) 0.9120(3) 0.0580(7) Uani 1 1 d . . .
C10 C 0.1094(6) 0.65615(7) 0.8401(2) 0.0555(6) Uani 1 1 d . . .
O4 O 0.0369(4) 0.35786(5) 0.74672(15) 0.0641(5) Uani 1 1 d . . .
O8 O 0.3052(4) 0.64737(5) 0.79644(16) 0.0757(6) Uani 1 1 d . . .
O7 O -0.0147(4) 0.69212(6) 0.83170(19) 0.0818(6) Uani 1 1 d . . .
O3 O 0.2318(4) 0.30252(5) 0.68309(16) 0.0746(6) Uani 1 1 d . . .
C17 C 0.7323(5) 0.55620(7) 1.11351(17) 0.0450(6) Uani 1 1 d . . .
C18 C 0.1230(5) 0.47985(6) 0.85967(18) 0.0445(6) Uani 1 1 d . . .
C9 C 0.3879(6) 0.51896(7) 0.63686(19) 0.0498(6) Uani 1 1 d . . .
C8 C -0.2696(5) 0.44382(7) 0.39977(18) 0.0518(6) Uani 1 1 d . . .
N1 N 0.2897(4) 0.40639(5) 0.59713(15) 0.0513(5) Uani 1 1 d . . .
N2 N 0.1251(4) 0.59043(5) 0.93650(15) 0.0478(5) Uani 1 1 d . . .
N3 N 0.5964(5) 0.25326(6) 0.91155(17) 0.0671(6) Uani 1 1 d . . .
C19 C 0.7418(6) 0.27350(8) 0.8471(2) 0.0625(7) Uani 1 1 d . . .
O9 O 0.8812(4) 0.25749(5) 0.78065(16) 0.0746(6) Uani 1 1 d . . .
C21 C 0.4405(7) 0.27353(9) 0.9889(2) 0.0844(9) Uani 1 1 d . . .
H21A H 0.4447 0.3028 0.9781 0.127 Uiso 1 1 calc R . .
H21B H 0.5179 0.2671 1.0607 0.127 Uiso 1 1 calc R . .
H21C H 0.2557 0.2640 0.9791 0.127 Uiso 1 1 calc R . .
C20 C 0.5824(11) 0.20854(9) 0.9075(3) 0.145(2) Uani 1 1 d . . .
H20A H 0.5872 0.1994 0.8345 0.218 Uiso 1 1 calc R . .
H20B H 0.4163 0.1995 0.9337 0.218 Uiso 1 1 calc R . .
H20C H 0.7344 0.1971 0.9518 0.218 Uiso 1 1 calc R . .
H8 H -0.348(4) 0.4182(6) 0.3712(16) 0.045(6) Uiso 1 1 d . . .
H9 H 0.533(5) 0.5187(7) 0.6872(19) 0.056(7) Uiso 1 1 d . . .
H18 H -0.019(5) 0.4787(6) 0.8112(17) 0.045(7) Uiso 1 1 d . . .
H17 H 0.792(4) 0.5808(6) 1.1499(16) 0.046(6) Uiso 1 1 d . . .
H2A H 0.549(7) 0.3734(9) 0.687(2) 0.098(11) Uiso 1 1 d . . .
H2B H 0.451(5) 0.3508(8) 0.574(2) 0.071(8) Uiso 1 1 d . . .
H11B H -0.209(6) 0.6196(8) 0.874(2) 0.078(9) Uiso 1 1 d . . .
H11A H -0.051(5) 0.6430(8) 0.979(2) 0.071(8) Uiso 1 1 d . . .
H19 H 0.730(5) 0.3047(8) 0.8536(18) 0.064(7) Uiso 1 1 d . . .
H7 H 0.064(9) 0.7120(14) 0.781(3) 0.159(16) Uiso 1 1 d . . .
H3 H 0.082(9) 0.2856(13) 0.726(3) 0.147(14) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0577(12) 0.0622(10) 0.0619(10) -0.0019(8) -0.0019(9) -0.0057(8)
O6 0.0767(13) 0.0375(9) 0.0759(11) -0.0113(8) 0.0080(9) -0.0006(8)
O2 0.0957(16) 0.0447(10) 0.0844(13) -0.0055(8) -0.0136(11) -0.0184(9)
O5 0.0639(13) 0.0607(11) 0.0774(12) -0.0006(9) -0.0135(10) 0.0061(9)
C14 0.0419(14) 0.0356(10) 0.0373(10) -0.0018(8) 0.0118(10) -0.0064(9)
C6 0.0535(16) 0.0479(13) 0.0398(11) -0.0042(9) 0.0099(11) -0.0143(11)
C5 0.0461(15) 0.0454(12) 0.0350(10) -0.0034(9) 0.0102(10) -0.0140(10)
C4 0.0477(15) 0.0489(13) 0.0375(11) 0.0001(9) 0.0108(11) -0.0104(10)
C15 0.0498(15) 0.0369(11) 0.0390(11) -0.0025(8) 0.0124(11) -0.0049(9)
C13 0.0454(15) 0.0408(12) 0.0411(11) -0.0010(9) 0.0127(11) -0.0026(9)
C16 0.0520(16) 0.0380(12) 0.0494(12) -0.0006(10) 0.0165(11) -0.0030(10)
C3 0.0498(16) 0.0545(14) 0.0408(12) -0.0015(10) 0.0097(12) -0.0108(11)
C7 0.0627(18) 0.0463(13) 0.0521(13) -0.0014(10) 0.0070(13) -0.0129(12)
C1 0.0531(17) 0.0422(13) 0.0590(14) -0.0015(10) 0.0025(13) -0.0001(11)
C12 0.0466(16) 0.0477(13) 0.0500(13) 0.0027(10) 0.0097(12) -0.0041(11)
C2 0.0512(18) 0.0502(14) 0.0757(18) -0.0033(13) 0.0100(15) 0.0002(12)
C11 0.0541(19) 0.0403(13) 0.0809(19) 0.0049(13) 0.0137(15) 0.0063(12)
C10 0.0548(18) 0.0404(13) 0.0706(16) 0.0065(11) 0.0041(14) 0.0045(11)
O4 0.0627(13) 0.0487(9) 0.0829(12) -0.0033(8) 0.0172(10) -0.0017(8)
O8 0.0741(15) 0.0663(12) 0.0908(13) 0.0213(9) 0.0289(12) 0.0123(10)
O7 0.0790(15) 0.0493(11) 0.1207(16) 0.0217(10) 0.0279(13) 0.0165(9)
O3 0.0865(16) 0.0396(9) 0.1011(14) -0.0009(9) 0.0254(12) 0.0041(9)
C17 0.0553(16) 0.0392(12) 0.0416(12) -0.0079(9) 0.0109(11) -0.0095(11)
C18 0.0463(16) 0.0485(13) 0.0387(12) -0.0027(10) 0.0034(11) -0.0077(11)
C9 0.0517(17) 0.0551(14) 0.0422(13) -0.0027(10) 0.0034(12) -0.0149(12)
C8 0.0627(18) 0.0451(13) 0.0477(13) -0.0055(10) 0.0065(12) -0.0174(12)
N1 0.0511(14) 0.0452(11) 0.0579(12) -0.0001(8) 0.0071(10) -0.0068(9)
N2 0.0458(13) 0.0379(10) 0.0606(11) 0.0019(8) 0.0102(10) 0.0002(8)
N3 0.0900(19) 0.0424(11) 0.0700(13) 0.0023(10) 0.0132(13) 0.0018(11)
C19 0.077(2) 0.0391(14) 0.0710(17) -0.0017(12) 0.0027(15) 0.0025(13)
O9 0.0949(16) 0.0406(9) 0.0924(13) -0.0034(9) 0.0292(12) -0.0039(9)
C21 0.098(3) 0.0697(19) 0.088(2) -0.0141(15) 0.0210(19) -0.0019(17)
C20 0.238(6) 0.0431(18) 0.175(4) 0.015(2) 0.122(4) 0.004(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
O1 C3 1.216(3) . ?
O6 C16 1.215(2) . ?
O2 C7 1.213(2) . ?
O5 C12 1.211(3) . ?
C14 C13 1.407(3) . ?
C14 C15 1.412(3) . ?
C14 C14 1.413(4) 3_667 ?
C6 C8 1.370(3) . ?
C6 C5 1.413(3) . ?
C6 C7 1.473(3) . ?
C5 C4 1.409(3) . ?
C5 C5 1.415(4) 3_566 ?
C4 C9 1.377(3) . ?
C4 C3 1.473(3) . ?
C15 C17 1.373(3) . ?
C15 C16 1.473(3) . ?
C13 C18 1.375(3) . ?
C13 C12 1.477(3) . ?
C16 N2 1.396(3) . ?
C3 N1 1.394(3) . ?
C7 N1 1.394(3) . ?
C1 O4 1.200(3) . ?
C1 O3 1.318(3) . ?
C1 C2 1.498(4) . ?
C12 N2 1.397(3) . ?
C2 N1 1.466(3) . ?
C2 H2A 0.94(3) . ?
C2 H2B 0.99(3) . ?
C11 N2 1.461(3) . ?
C11 C10 1.496(4) . ?
C11 H11B 0.99(3) . ?
C11 H11A 0.97(3) . ?
C10 O8 1.192(3) . ?
C10 O7 1.317(3) . ?
O7 H7 1.01(5) . ?
O3 H3 1.10(5) . ?
C17 C18 1.393(3) 3_667 ?
C17 H17 0.95(2) . ?
C18 C17 1.393(3) 3_667 ?
C18 H18 0.88(2) . ?
C9 C8 1.397(3) 3_566 ?
C9 H9 0.90(2) . ?
C8 C9 1.397(3) 3_566 ?
C8 H8 0.97(2) . ?
N3 C19 1.309(3) . ?
N3 C20 1.451(4) . ?
N3 C21 1.453(4) . ?
C19 O9 1.244(3) . ?
C19 H19 1.02(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C13 C14 C15 121.44(19) . . ?
C13 C14 C14 119.4(2) . 3_667 ?
C15 C14 C14 119.1(2) . 3_667 ?
C8 C6 C5 120.1(2) . . ?
C8 C6 C7 120.84(19) . . ?
C5 C6 C7 119.0(2) . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 C5 119.3(2) . 3_566 ?
C6 C5 C5 119.3(3) . 3_566 ?
C9 C4 C5 119.9(2) . . ?
C9 C4 C3 120.2(2) . . ?
C5 C4 C3 119.89(18) . . ?
C17 C15 C14 120.2(2) . . ?
C17 C15 C16 120.42(18) . . ?
C14 C15 C16 119.4(2) . . ?
C18 C13 C14 120.1(2) . . ?
C18 C13 C12 120.1(2) . . ?
C14 C13 C12 119.83(18) . . ?
O6 C16 N2 119.7(2) . . ?
O6 C16 C15 123.0(2) . . ?
N2 C16 C15 117.36(18) . . ?
O1 C3 N1 120.2(2) . . ?
O1 C3 C4 122.9(2) . . ?
N1 C3 C4 116.9(2) . . ?
O2 C7 N1 119.5(2) . . ?
O2 C7 C6 122.7(2) . . ?
N1 C7 C6 117.79(19) . . ?
O4 C1 O3 123.7(2) . . ?
O4 C1 C2 124.4(2) . . ?
O3 C1 C2 111.9(2) . . ?
O5 C12 N2 120.2(2) . . ?
O5 C12 C13 123.0(2) . . ?
N2 C12 C13 116.8(2) . . ?
N1 C2 C1 111.8(2) . . ?
N1 C2 H2A 105.2(18) . . ?
C1 C2 H2A 108(2) . . ?
N1 C2 H2B 107.8(14) . . ?
C1 C2 H2B 109.6(15) . . ?
H2A C2 H2B 114(3) . . ?
N2 C11 C10 111.4(2) . . ?
N2 C11 H11B 106.6(15) . . ?
C10 C11 H11B 109.1(15) . . ?
N2 C11 H11A 109.4(15) . . ?
C10 C11 H11A 107.9(15) . . ?
H11B C11 H11A 112(2) . . ?
O8 C10 O7 124.7(2) . . ?
O8 C10 C11 125.3(2) . . ?
O7 C10 C11 110.1(3) . . ?
C10 O7 H7 114(3) . . ?
C1 O3 H3 110(2) . . ?
C15 C17 C18 120.5(2) . 3_667 ?
C15 C17 H17 122.0(12) . . ?
C18 C17 H17 117.5(13) 3_667 . ?
C13 C18 C17 120.7(2) . 3_667 ?
C13 C18 H18 120.3(13) . . ?
C17 C18 H18 119.0(13) 3_667 . ?
C4 C9 C8 120.8(2) . 3_566 ?
C4 C9 H9 118.4(14) . . ?
C8 C9 H9 120.8(14) 3_566 . ?
C6 C8 C9 120.5(2) . 3_566 ?
C6 C8 H8 120.6(12) . . ?
C9 C8 H8 118.9(12) 3_566 . ?
C7 N1 C3 124.74(19) . . ?
C7 N1 C2 115.91(19) . . ?
C3 N1 C2 119.3(2) . . ?
C16 N2 C12 125.01(18) . . ?
C16 N2 C11 116.9(2) . . ?
C12 N2 C11 118.0(2) . . ?
C19 N3 C20 120.4(3) . . ?
C19 N3 C21 123.0(2) . . ?
C20 N3 C21 116.6(2) . . ?
O9 C19 N3 125.2(2) . . ?
O9 C19 H19 120.6(14) . . ?
N3 C19 H19 114.1(14) . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
C8 C6 C5 C4 -178.4(2) . . . . ?
C7 C6 C5 C4 2.6(3) . . . . ?
C8 C6 C5 C5 0.8(4) . . . 3_566 ?
C7 C6 C5 C5 -178.1(2) . . . 3_566 ?
C6 C5 C4 C9 -179.2(2) . . . . ?
C5 C5 C4 C9 1.5(4) 3_566 . . . ?
C6 C5 C4 C3 1.1(3) . . . . ?
C5 C5 C4 C3 -178.2(2) 3_566 . . . ?
C13 C14 C15 C17 -178.9(2) . . . . ?
C14 C14 C15 C17 1.6(4) 3_667 . . . ?
C13 C14 C15 C16 1.6(3) . . . . ?
C14 C14 C15 C16 -177.8(2) 3_667 . . . ?
C15 C14 C13 C18 -178.9(2) . . . . ?
C14 C14 C13 C18 0.5(4) 3_667 . . . ?
C15 C14 C13 C12 0.3(3) . . . . ?
C14 C14 C13 C12 179.8(2) 3_667 . . . ?
C17 C15 C16 O6 -0.8(3) . . . . ?
C14 C15 C16 O6 178.7(2) . . . . ?
C17 C15 C16 N2 179.7(2) . . . . ?
C14 C15 C16 N2 -0.8(3) . . . . ?
C9 C4 C3 O1 -4.7(4) . . . . ?
C5 C4 C3 O1 175.0(2) . . . . ?
C9 C4 C3 N1 175.1(2) . . . . ?
C5 C4 C3 N1 -5.2(3) . . . . ?
C8 C6 C7 O2 -1.3(4) . . . . ?
C5 C6 C7 O2 177.6(2) . . . . ?
C8 C6 C7 N1 178.9(2) . . . . ?
C5 C6 C7 N1 -2.1(3) . . . . ?
C18 C13 C12 O5 -2.5(3) . . . . ?
C14 C13 C12 O5 178.2(2) . . . . ?
C18 C13 C12 N2 176.2(2) . . . . ?
C14 C13 C12 N2 -3.1(3) . . . . ?
O4 C1 C2 N1 -33.9(4) . . . . ?
O3 C1 C2 N1 148.9(2) . . . . ?
N2 C11 C10 O8 8.8(4) . . . . ?
N2 C11 C10 O7 -171.2(2) . . . . ?
C14 C15 C17 C18 -1.7(3) . . . 3_667 ?
C16 C15 C17 C18 177.8(2) . . . 3_667 ?
C14 C13 C18 C17 -0.5(3) . . . 3_667 ?
C12 C13 C18 C17 -179.8(2) . . . 3_667 ?
C5 C4 C9 C8 -0.7(4) . . . 3_566 ?
C3 C4 C9 C8 178.9(2) . . . 3_566 ?
C5 C6 C8 C9 -1.6(4) . . . 3_566 ?
C7 C6 C8 C9 177.3(2) . . . 3_566 ?
O2 C7 N1 C3 177.9(2) . . . . ?
C6 C7 N1 C3 -2.3(3) . . . . ?
O2 C7 N1 C2 0.4(3) . . . . ?
C6 C7 N1 C2 -179.8(2) . . . . ?
O1 C3 N1 C7 -174.3(2) . . . . ?
C4 C3 N1 C7 5.9(3) . . . . ?
O1 C3 N1 C2 3.2(3) . . . . ?
C4 C3 N1 C2 -176.7(2) . . . . ?
C1 C2 N1 C7 -63.3(3) . . . . ?
C1 C2 N1 C3 119.1(3) . . . . ?
O6 C16 N2 C12 178.3(2) . . . . ?
C15 C16 N2 C12 -2.2(3) . . . . ?
O6 C16 N2 C11 0.5(3) . . . . ?
C15 C16 N2 C11 179.94(19) . . . . ?
O5 C12 N2 C16 -177.2(2) . . . . ?
C13 C12 N2 C16 4.1(3) . . . . ?
O5 C12 N2 C11 0.7(3) . . . . ?
C13 C12 N2 C11 -178.1(2) . . . . ?
C10 C11 N2 C16 77.5(3) . . . . ?
C10 C11 N2 C12 -100.5(3) . . . . ?
C20 N3 C19 O9 -1.6(5) . . . . ?
C21 N3 C19 O9 179.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.035

# Attachment 'dmsosolvate.cif'

data_napglydmso
_database_code_depnum_ccdc_archive 'CCDC 614262'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N2 O9 S'
_chemical_formula_weight         460.41

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)/m

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

_cell_length_a                   5.0358(4)
_cell_length_b                   31.895(3)
_cell_length_c                   6.6096(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.033(4)
_cell_angle_gamma                90.00
_cell_volume                     1025.29(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plates
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10389
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         25.50
_reflns_number_total             1853
_reflns_number_gt                960
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.2000P)^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         1853
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1554
_refine_ls_R_factor_gt           0.0880
_refine_ls_wR_factor_ref         0.3210
_refine_ls_wR_factor_gt          0.2664
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.414
_refine_ls_shift/su_mean         0.036

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 0.7019(18) 0.7500 0.2875(15) 0.170(4) Uani 0.50 2 d SP . .
C10 C 0.809(6) 0.7135(7) 0.321(4) 0.55(3) Uani 1 1 d . . .
H10A H 0.9899 0.7139 0.2995 0.831 Uiso 1 1 calc R . .
H10B H 0.6966 0.6938 0.2267 0.831 Uiso 1 1 calc R . .
H10C H 0.8198 0.7053 0.4631 0.831 Uiso 1 1 calc R . .
C5 C 0.4364(8) 0.51823(14) 0.5251(7) 0.0555(12) Uani 1 1 d . . .
N1 N 0.1754(7) 0.58924(12) 0.6354(7) 0.0685(12) Uani 1 1 d . . .
C6 C 0.4496(9) 0.55617(14) 0.4239(8) 0.0595(13) Uani 1 1 d . . .
C4 C 0.2931(9) 0.51471(15) 0.6841(7) 0.0603(13) Uani 1 1 d . . .
C3 C 0.1553(10) 0.55243(17) 0.7399(9) 0.0692(14) Uani 1 1 d . . .
C7 C 0.3174(10) 0.59399(17) 0.4815(9) 0.0690(14) Uani 1 1 d . . .
C8 C 0.5911(10) 0.55827(15) 0.2703(8) 0.0666(14) Uani 1 1 d . . .
H8 H 0.5996 0.5834 0.2008 0.080 Uiso 1 1 calc R . .
O1 O 0.0268(9) 0.55126(11) 0.8721(7) 0.0928(13) Uani 1 1 d . . .
C9 C 0.2794(10) 0.47741(16) 0.7797(8) 0.0658(14) Uani 1 1 d . . .
H9 H 0.1813 0.4756 0.8808 0.079 Uiso 1 1 calc R . .
O2 O 0.3313(9) 0.62837(12) 0.4037(6) 0.0904(13) Uani 1 1 d . . .
C2 C 0.0518(11) 0.62724(17) 0.6940(10) 0.0808(17) Uani 1 1 d . . .
H2A H -0.0819 0.6197 0.7703 0.097 Uiso 1 1 calc R . .
H2B H -0.0434 0.6423 0.5686 0.097 Uiso 1 1 calc R . .
C1 C 0.2671(13) 0.65490(16) 0.8274(9) 0.0763(16) Uani 1 1 d . . .
O3 O 0.1576(10) 0.69276(13) 0.8379(8) 0.1167(17) Uani 1 1 d . . .
H3 H 0.2419 0.7046 0.9456 0.175 Uiso 1 1 calc R . .
O4 O 0.4991(9) 0.64541(13) 0.9077(7) 0.0917(13) Uani 1 1 d . . .
O5 O 0.4544(16) 0.7500 0.0761(14) 0.141(3) Uani 1 2 d S . .
S2 S 0.7626(13) 0.7500 0.1210(14) 0.125(2) Uani 0.50 2 d SP . .

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
S1 0.158(7) 0.256(13) 0.077(4) 0.000 -0.004(4) 0.000
C10 0.55(4) 0.32(2) 0.51(4) 0.31(3) -0.38(4) -0.25(3)
C5 0.045(2) 0.066(3) 0.052(3) -0.005(2) 0.006(2) -0.0079(18)
N1 0.054(2) 0.061(3) 0.089(3) -0.007(2) 0.016(2) -0.0041(18)
C6 0.054(3) 0.061(3) 0.060(3) 0.006(2) 0.009(2) -0.007(2)
C4 0.055(3) 0.065(3) 0.056(3) -0.006(2) 0.006(2) -0.009(2)
C3 0.059(3) 0.077(4) 0.071(4) -0.012(3) 0.015(3) -0.007(2)
C7 0.070(3) 0.061(3) 0.075(4) -0.002(3) 0.019(3) -0.003(2)
C8 0.075(3) 0.059(3) 0.064(3) 0.004(2) 0.016(3) -0.008(2)
O1 0.097(3) 0.091(3) 0.105(3) -0.006(2) 0.052(3) 0.000(2)
C9 0.064(3) 0.079(4) 0.058(3) 0.003(3) 0.021(2) -0.013(2)
O2 0.116(3) 0.065(3) 0.095(3) 0.015(2) 0.036(2) 0.010(2)
C2 0.068(3) 0.075(4) 0.101(4) -0.008(3) 0.024(3) 0.000(2)
C1 0.090(4) 0.055(3) 0.088(4) -0.008(3) 0.030(3) 0.002(3)
O3 0.109(3) 0.078(3) 0.151(5) -0.026(3) 0.012(3) 0.012(2)
O4 0.075(2) 0.082(3) 0.115(3) -0.013(2) 0.021(2) 0.000(2)
O5 0.124(6) 0.071(4) 0.193(7) 0.000 -0.022(5) 0.000
S2 0.122(5) 0.085(4) 0.146(6) 0.000 -0.006(4) 0.000

_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 C10 1.28(3) 4_575 ?
S1 C10 1.28(3) . ?
S1 O5 1.613(11) . ?
C5 C6 1.393(6) . ?
C5 C5 1.408(9) 3_666 ?
C5 C4 1.425(7) . ?
N1 C3 1.379(7) . ?
N1 C7 1.395(6) . ?
N1 C2 1.460(6) . ?
C6 C8 1.385(7) . ?
C6 C7 1.475(7) . ?
C4 C9 1.357(7) . ?
C4 C3 1.483(7) . ?
C3 O1 1.215(6) . ?
C7 O2 1.221(6) . ?
C8 C9 1.393(7) 3_666 ?
C9 C8 1.393(7) 3_666 ?
C2 C1 1.495(8) . ?
C1 O4 1.190(6) . ?
C1 O3 1.337(6) . ?
S2 C10 1.733(16) 4_575 ?

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
C10 S1 C10 131(2) 4_575 . ?
C10 S1 O5 110.3(9) 4_575 . ?
C10 S1 O5 110.3(9) . . ?
C6 C5 C5 121.5(6) . 3_666 ?
C6 C5 C4 121.3(4) . . ?
C5 C5 C4 117.2(5) 3_666 . ?
C3 N1 C7 125.2(4) . . ?
C3 N1 C2 118.8(5) . . ?
C7 N1 C2 116.0(4) . . ?
C8 C6 C5 119.5(4) . . ?
C8 C6 C7 120.1(4) . . ?
C5 C6 C7 120.4(5) . . ?
C9 C4 C5 120.6(5) . . ?
C9 C4 C3 120.8(5) . . ?
C5 C4 C3 118.6(5) . . ?
O1 C3 N1 120.6(5) . . ?
O1 C3 C4 121.7(5) . . ?
N1 C3 C4 117.8(5) . . ?
O2 C7 N1 120.0(5) . . ?
O2 C7 C6 123.2(5) . . ?
N1 C7 C6 116.8(5) . . ?
C6 C8 C9 119.7(4) . 3_666 ?
C4 C9 C8 121.5(5) . 3_666 ?
N1 C2 C1 110.6(4) . . ?
O4 C1 O3 125.2(5) . . ?
O4 C1 C2 126.2(5) . . ?
O3 C1 C2 108.5(5) . . ?

_diffrn_measured_fraction_theta_max 0.955
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.955
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.067