# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xxx
_database_code_depnum_ccdc_archive 'CCDC 1432433'
_audit_update_record             
;
2015-10-21 deposited with the CCDC.
2016-03-17 downloaded from the CCDC.
;

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

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 N4 O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C15 H10 N4 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         262.27
_chemical_compound_source        ?

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

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

# 6. CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_symmetry_Int_Tables_number      29

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

_cell_length_a                   13.301(3)
_cell_length_b                   13.892(4)
_cell_length_c                   6.7933(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1255.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1576
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      25.3
_cell_special_details            
;
;

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.110

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.990

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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'


_diffrn_reflns_number            7990
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.31
_reflns_number_total             2203
_reflns_number_gt                1726
_reflns_threshold_expression     >2sigma(I)

_diffrn_reflns_theta_full        25.31
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'

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

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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)+(0.0372P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.9(17)
_refine_ls_number_reflns         2203
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0825
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_restrained_S_all      0.918
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_refine_diff_density_max         0.098
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.025

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

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uani 0.73350(10) 0.07444(10) 0.1275(2) 1.000 0.0655(5) . .
N1 N Uani 0.80250(11) 0.25697(14) 0.2199(3) 1.000 0.0672(6) . .
N2 N Uani 0.80962(13) 0.35379(14) 0.2545(3) 1.000 0.0747(7) . .
N3 N Uani 0.72186(13) 0.39258(13) 0.2656(3) 1.000 0.0693(7) . .
N4 N Uani 0.65396(11) 0.32081(11) 0.2377(2) 1.000 0.0554(6) . .
C1 C Uani 0.51786(17) -0.07770(17) 0.1861(3) 1.000 0.0700(8) . .
C2 C Uani 0.5581(2) -0.16634(18) 0.1371(4) 1.000 0.0763(10) . .
C3 C Uani 0.6572(2) -0.17630(18) 0.0816(4) 1.000 0.0817(10) . .
C4 C Uani 0.72113(19) -0.10000(17) 0.0740(4) 1.000 0.0747(10) . .
C5 C Uani 0.68168(14) -0.01190(15) 0.1239(3) 1.000 0.0580(8) . .
C6 C Uani 0.58259(14) 0.00285(14) 0.1785(3) 1.000 0.0556(7) . .
C7 C Uani 0.66409(14) 0.14236(15) 0.1847(3) 1.000 0.0546(7) . .
C8 C Uani 0.57369(13) 0.10391(15) 0.2143(3) 1.000 0.0563(7) . .
C9 C Uani 0.70521(12) 0.23843(15) 0.2101(3) 1.000 0.0546(6) . .
C10 C Uani 0.54852(13) 0.34471(13) 0.2331(3) 1.000 0.0548(7) . .
C11 C Uani 0.50904(16) 0.39915(14) 0.3818(4) 1.000 0.0662(8) . .
C12 C Uani 0.40916(19) 0.42623(16) 0.3692(4) 1.000 0.0808(10) . .
C13 C Uani 0.35109(17) 0.39908(16) 0.2121(5) 1.000 0.0789(9) . .
C14 C Uani 0.39224(17) 0.34372(18) 0.0650(4) 1.000 0.0757(9) . .
C15 C Uani 0.49230(16) 0.31702(16) 0.0733(3) 1.000 0.0653(8) . .
H1 H Uiso 0.45080 -0.07140 0.22270 1.000 0.0840 calc R
H2 H Uiso 0.51720 -0.22060 0.14180 1.000 0.0920 calc R
H3 H Uiso 0.68100 -0.23710 0.04830 1.000 0.0980 calc R
H4 H Uiso 0.78800 -0.10710 0.03710 1.000 0.0900 calc R
H8 H Uiso 0.51570 0.13660 0.25130 1.000 0.0680 calc R
H11 H Uiso 0.54830 0.41750 0.48870 1.000 0.0790 calc R
H12 H Uiso 0.38100 0.46340 0.46880 1.000 0.0970 calc R
H13 H Uiso 0.28410 0.41800 0.20510 1.000 0.0950 calc R
H14 H Uiso 0.35260 0.32420 -0.04050 1.000 0.0910 calc R
H15 H Uiso 0.52100 0.28100 -0.02750 1.000 0.0780 calc R


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

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.384(2) . . yes
O1 C7 1.376(2) . . yes
N1 N2 1.369(3) . . yes
N1 C9 1.321(2) . . yes
N2 N3 1.288(3) . . yes
N3 N4 1.359(2) . . yes
N4 C9 1.345(3) . . yes
N4 C10 1.442(2) . . yes
C1 C2 1.383(3) . . no
C1 C6 1.413(3) . . no
C2 C3 1.378(4) . . no
C3 C4 1.360(4) . . no
C4 C5 1.374(3) . . no
C5 C6 1.384(3) . . no
C6 C8 1.430(3) . . no
C7 C8 1.331(3) . . no
C7 C9 1.453(3) . . no
C10 C11 1.367(3) . . no
C10 C15 1.373(3) . . no
C11 C12 1.383(3) . . no
C12 C13 1.370(4) . . no
C13 C14 1.375(4) . . no
C14 C15 1.383(3) . . no
C1 H1 0.9300 . . no
C2 H2 0.9300 . . no
C3 H3 0.9300 . . no
C4 H4 0.9300 . . no
C8 H8 0.9300 . . no
C11 H11 0.9300 . . no
C12 H12 0.9300 . . no
C13 H13 0.9300 . . no
C14 H14 0.9300 . . no
C15 H15 0.9300 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C7 105.38(14) . . . yes
N2 N1 C9 105.55(16) . . . yes
N1 N2 N3 111.01(16) . . . yes
N2 N3 N4 106.70(16) . . . yes
N3 N4 C9 107.87(15) . . . yes
N3 N4 C10 118.73(15) . . . yes
C9 N4 C10 133.31(15) . . . yes
C2 C1 C6 117.4(2) . . . no
C1 C2 C3 121.7(2) . . . no
C2 C3 C4 122.0(2) . . . no
C3 C4 C5 116.5(2) . . . no
O1 C5 C4 125.89(18) . . . yes
O1 C5 C6 109.95(17) . . . yes
C4 C5 C6 124.2(2) . . . no
C1 C6 C5 118.21(19) . . . no
C1 C6 C8 136.14(18) . . . no
C5 C6 C8 105.65(17) . . . no
O1 C7 C8 111.94(18) . . . yes
O1 C7 C9 114.26(16) . . . yes
C8 C7 C9 133.70(19) . . . no
C6 C8 C7 107.07(17) . . . no
N1 C9 N4 108.87(18) . . . yes
N1 C9 C7 123.64(18) . . . yes
N4 C9 C7 127.40(15) . . . yes
N4 C10 C11 119.03(17) . . . yes
N4 C10 C15 118.84(17) . . . yes
C11 C10 C15 122.01(18) . . . no
C10 C11 C12 118.3(2) . . . no
C11 C12 C13 121.0(2) . . . no
C12 C13 C14 119.7(2) . . . no
C13 C14 C15 120.2(2) . . . no
C10 C15 C14 118.8(2) . . . no
C2 C1 H1 121.00 . . . no
C6 C1 H1 121.00 . . . no
C1 C2 H2 119.00 . . . no
C3 C2 H2 119.00 . . . no
C2 C3 H3 119.00 . . . no
C4 C3 H3 119.00 . . . no
C3 C4 H4 122.00 . . . no
C5 C4 H4 122.00 . . . no
C6 C8 H8 126.00 . . . no
C7 C8 H8 126.00 . . . no
C10 C11 H11 121.00 . . . no
C12 C11 H11 121.00 . . . no
C11 C12 H12 120.00 . . . no
C13 C12 H12 120.00 . . . no
C12 C13 H13 120.00 . . . no
C14 C13 H13 120.00 . . . no
C13 C14 H14 120.00 . . . no
C15 C14 H14 120.00 . . . no
C10 C15 H15 121.00 . . . no
C14 C15 H15 121.00 . . . no

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
C7 O1 C5 C6 -0.2(2) . . . . no
C5 O1 C7 C8 -0.6(2) . . . . no
C5 O1 C7 C9 176.27(17) . . . . no
C7 O1 C5 C4 179.8(2) . . . . no
C9 N1 N2 N3 0.1(3) . . . . no
N2 N1 C9 N4 0.0(2) . . . . no
N2 N1 C9 C7 -176.81(19) . . . . no
N1 N2 N3 N4 -0.1(2) . . . . no
N2 N3 N4 C9 0.1(2) . . . . no
N2 N3 N4 C10 -177.03(17) . . . . no
N3 N4 C9 N1 0.0(2) . . . . no
C10 N4 C9 N1 176.48(19) . . . . no
N3 N4 C9 C7 176.6(2) . . . . no
C10 N4 C9 C7 -6.9(3) . . . . no
C9 N4 C10 C15 -50.7(3) . . . . no
N3 N4 C10 C11 -50.6(2) . . . . no
N3 N4 C10 C15 125.5(2) . . . . no
C9 N4 C10 C11 133.2(2) . . . . no
C2 C1 C6 C5 -0.3(3) . . . . no
C2 C1 C6 C8 179.6(2) . . . . no
C6 C1 C2 C3 -0.4(4) . . . . no
C1 C2 C3 C4 0.8(4) . . . . no
C2 C3 C4 C5 -0.3(4) . . . . no
C3 C4 C5 C6 -0.5(4) . . . . no
C3 C4 C5 O1 179.5(2) . . . . no
C4 C5 C6 C1 0.8(3) . . . . no
O1 C5 C6 C1 -179.17(17) . . . . no
C4 C5 C6 C8 -179.1(2) . . . . no
O1 C5 C6 C8 0.9(2) . . . . no
C5 C6 C8 C7 -1.2(2) . . . . no
C1 C6 C8 C7 178.8(2) . . . . no
O1 C7 C9 N1 -13.9(3) . . . . no
C9 C7 C8 C6 -174.9(2) . . . . no
C8 C7 C9 N4 -14.1(4) . . . . no
O1 C7 C9 N4 169.94(18) . . . . no
C8 C7 C9 N1 162.1(2) . . . . no
O1 C7 C8 C6 1.2(2) . . . . no
N4 C10 C11 C12 176.23(19) . . . . no
C15 C10 C11 C12 0.3(3) . . . . no
N4 C10 C15 C14 -177.14(19) . . . . no
C11 C10 C15 C14 -1.2(3) . . . . no
C10 C11 C12 C13 0.2(3) . . . . no
C11 C12 C13 C14 0.3(4) . . . . no
C12 C13 C14 C15 -1.3(4) . . . . no
C13 C14 C15 C10 1.7(4) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 N1 2.769(2) . . no
N1 O1 2.769(2) . . no
N1 N4 2.169(2) . . no
N1 C9 3.342(3) . 3_655 no
N2 C15 3.449(3) . 3_655 no
N2 N4 2.124(2) . . no
N2 C12 3.420(3) . 4_565 no
N3 C13 3.386(3) . 4_565 no
N4 N1 2.169(2) . . no
N1 H2 2.9500 . 4_555 no
N1 H15 2.9300 . 3_655 no
N2 H11 2.7600 . 3_654 no
N2 H15 2.8800 . 3_655 no
N3 H13 2.7900 . 4_565 no
N3 H11 2.7800 . . no
C1 C8 3.448(3) . 2_654 no
C2 C8 3.475(3) . 2_654 no
C4 C5 3.538(3) . 3_654 no
C4 C4 3.482(4) . 3_655 no
C4 C4 3.482(4) . 3_654 no
C5 C4 3.538(3) . 3_655 no
C7 C15 3.418(3) . . no
C8 C10 3.364(3) . . no
C8 C2 3.475(3) . 2_655 no
C8 C15 3.295(3) . . no
C8 C1 3.448(3) . 2_655 no
C9 N1 3.342(3) . 3_654 no
C9 C9 3.600(3) . 3_654 no
C9 C9 3.600(3) . 3_655 no
C10 C8 3.364(3) . . no
C12 N2 3.420(3) . 4_465 no
C13 N3 3.386(3) . 4_465 no
C15 C7 3.418(3) . . no
C15 C8 3.295(3) . . no
C15 N2 3.449(3) . 3_654 no
C1 H8 3.1000 . 2_654 no
C2 H8 2.8300 . 2_654 no
C2 H15 2.9700 . 2_655 no
C7 H15 3.0700 . . no
C8 H15 3.0400 . . no
C9 H15 2.9900 . . no
C10 H8 2.9300 . . no
C11 H2 3.0600 . 2_655 no
C15 H8 2.8000 . . no
H2 C11 3.0600 . 2_654 no
H2 H15 2.4500 . 2_655 no
H2 N1 2.9500 . 4_455 no
H8 C10 2.9300 . . no
H8 C15 2.8000 . . no
H8 C1 3.1000 . 2_655 no
H8 C2 2.8300 . 2_655 no
H11 N3 2.7800 . . no
H11 N2 2.7600 . 3_655 no
H13 N3 2.7900 . 4_465 no
H15 C7 3.0700 . . no
H15 C8 3.0400 . . no
H15 C9 2.9900 . . no
H15 C2 2.9700 . 2_654 no
H15 H2 2.4500 . 2_654 no
H15 N1 2.9300 . 3_654 no
H15 N2 2.8800 . 3_654 no

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xxx
_database_code_depnum_ccdc_archive 'CCDC 1433117'
_audit_update_record             
;
2015-10-26 deposited with the CCDC.
2016-03-17 downloaded from the CCDC.
;

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

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H22 N4 O2 S'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C24 H22 N4 O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         430.53
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 21'
_symmetry_Int_Tables_number      4

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

_cell_length_a                   8.431(2)
_cell_length_b                   12.486(3)
_cell_length_c                   10.251(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.558(5)
_cell_angle_gamma                90
_cell_volume                     1079.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293
_cell_measurement_reflns_used    1520
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      25.4
_cell_special_details            
;
;

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.200

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  0.965

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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_reflns_number            7344
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         25.36
_reflns_number_total             3637
_reflns_number_gt                2940
_reflns_threshold_expression     >2sigma(I)

_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989

_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'

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

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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)+(0.0483P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_number_reflns         3637
_refine_ls_number_parameters     280
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.948
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.074

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

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S Uani 0.51418(8) 0.97200(6) 0.17989(6) 1.000 0.0586(2) . .
O1 O Uani 0.4797(3) 1.07962(18) 0.2140(2) 1.000 0.0754(8) . .
O2 O Uani 0.3976(2) 0.89056(18) 0.19804(18) 1.000 0.0703(7) . .
N1 N Uani 0.5792(3) 0.7018(2) 0.4069(3) 1.000 0.0879(11) . .
N2 N Uani 0.4856(3) 0.7626(2) 0.4564(2) 1.000 0.0682(9) . .
N3 N Uani 0.4013(4) 0.8131(3) 0.5137(3) 1.000 0.0998(14) . .
N4 N Uani 0.6724(3) 0.93633(16) 0.27197(19) 1.000 0.0538(8) . .
C1 C Uani 1.0780(3) 0.9980(3) 0.3482(3) 1.000 0.0662(13) . .
C2 C Uani 1.0856(4) 1.1061(3) 0.3495(3) 1.000 0.0777(14) . .
C3 C Uani 0.9505(5) 1.1665(3) 0.3229(3) 1.000 0.0791(14) . .
C4 C Uani 0.8065(4) 1.1196(2) 0.2942(3) 1.000 0.0703(11) . .
C5 C Uani 0.8001(3) 1.0081(2) 0.2922(2) 1.000 0.0527(10) . .
C6 C Uani 0.9352(3) 0.9479(2) 0.3186(2) 1.000 0.0523(9) . .
C7 C Uani 0.7362(3) 0.8298(2) 0.2794(2) 1.000 0.0512(9) . .
C8 C Uani 0.8922(3) 0.8366(2) 0.3111(2) 1.000 0.0539(9) . .
C9 C Uani 1.0089(4) 0.7482(3) 0.3389(3) 1.000 0.0747(12) . .
C10 C Uani 0.6334(3) 0.7312(2) 0.2732(3) 1.000 0.0593(9) . .
C11 C Uani 0.7143(3) 0.6351(2) 0.2127(2) 1.000 0.0533(9) . .
C12 C Uani 0.7147(3) 0.5365(2) 0.2717(3) 1.000 0.0605(10) . .
C13 C Uani 0.7845(4) 0.4503(3) 0.2116(3) 1.000 0.0665(11) . .
C14 C Uani 0.8564(3) 0.4588(3) 0.0908(2) 1.000 0.0583(9) . .
C15 C Uani 0.8543(3) 0.5583(3) 0.0325(3) 1.000 0.0630(10) . .
C16 C Uani 0.7851(3) 0.6449(2) 0.0918(3) 1.000 0.0607(10) . .
C17 C Uani 0.9312(4) 0.3649(3) 0.0249(3) 1.000 0.0800(12) . .
C18 C Uani 0.5825(3) 0.9670(3) 0.0189(2) 1.000 0.0549(8) . .
C19 C Uani 0.6551(4) 1.0557(3) -0.0337(3) 1.000 0.0693(11) . .
C20 C Uani 0.7146(4) 1.0494(3) -0.1582(3) 1.000 0.0790(14) . .
C21 C Uani 0.7034(3) 0.9573(3) -0.2315(3) 1.000 0.0724(12) . .
C22 C Uani 0.6307(4) 0.8701(3) -0.1760(3) 1.000 0.0719(11) . .
C23 C Uani 0.5684(3) 0.8741(3) -0.0523(3) 1.000 0.0638(11) . .
C24 C Uani 0.7698(5) 0.9523(4) -0.3680(3) 1.000 0.1085(18) . .
H1 H Uiso 1.16800 0.95740 0.36690 1.000 0.0800 calc R
H2 H Uiso 1.18120 1.14010 0.36820 1.000 0.0930 calc R
H3 H Uiso 0.95770 1.24080 0.32450 1.000 0.0950 calc R
H4 H Uiso 0.71690 1.16080 0.27680 1.000 0.0840 calc R
H9A H Uiso 1.11120 0.77850 0.35770 1.000 0.1120 calc R
H9B H Uiso 1.01600 0.70220 0.26420 1.000 0.1120 calc R
H9C H Uiso 0.97390 0.70740 0.41270 1.000 0.1120 calc R
H10 H Uiso 0.53940 0.74820 0.22020 1.000 0.0710 calc R
H12 H Uiso 0.66760 0.52790 0.35270 1.000 0.0730 calc R
H13 H Uiso 0.78340 0.38410 0.25330 1.000 0.0800 calc R
H15 H Uiso 0.90080 0.56700 -0.04870 1.000 0.0760 calc R
H16 H Uiso 0.78580 0.71110 0.05020 1.000 0.0730 calc R
H17A H Uiso 0.92180 0.30270 0.07940 1.000 0.1200 calc R
H17B H Uiso 1.04130 0.37970 0.00990 1.000 0.1200 calc R
H17C H Uiso 0.87840 0.35200 -0.05710 1.000 0.1200 calc R
H19 H Uiso 0.66390 1.11880 0.01410 1.000 0.0830 calc R
H20 H Uiso 0.76370 1.10920 -0.19380 1.000 0.0950 calc R
H22 H Uiso 0.62340 0.80670 -0.22320 1.000 0.0860 calc R
H23 H Uiso 0.51740 0.81470 -0.01750 1.000 0.0760 calc R
H24A H Uiso 0.75230 0.88220 -0.40380 1.000 0.1630 calc R
H24B H Uiso 0.88160 0.96690 -0.36500 1.000 0.1630 calc R
H24C H Uiso 0.71770 1.00470 -0.42200 1.000 0.1630 calc R


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

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.419(2) . . yes
S1 O2 1.428(2) . . yes
S1 N4 1.687(2) . . yes
S1 C18 1.754(2) . . yes
N1 N2 1.210(4) . . yes
N1 C10 1.495(4) . . yes
N2 N3 1.121(4) . . yes
N4 C5 1.415(3) . . yes
N4 C7 1.437(3) . . yes
C1 C2 1.351(5) . . no
C1 C6 1.388(4) . . no
C2 C3 1.391(5) . . no
C3 C4 1.377(5) . . no
C4 C5 1.393(4) . . no
C5 C6 1.389(4) . . no
C6 C8 1.438(4) . . no
C7 C8 1.354(4) . . no
C7 C10 1.507(4) . . no
C8 C9 1.504(4) . . no
C10 C11 1.516(4) . . no
C11 C12 1.372(4) . . no
C11 C16 1.386(4) . . no
C12 C13 1.375(4) . . no
C13 C14 1.388(4) . . no
C14 C15 1.379(5) . . no
C14 C17 1.496(5) . . no
C15 C16 1.373(4) . . no
C18 C19 1.378(5) . . no
C18 C23 1.375(5) . . no
C19 C20 1.378(4) . . no
C20 C21 1.376(5) . . no
C21 C22 1.375(5) . . no
C21 C24 1.513(4) . . no
C22 C23 1.378(4) . . no
C1 H1 0.9300 . . no
C2 H2 0.9300 . . no
C3 H3 0.9300 . . no
C4 H4 0.9300 . . no
C9 H9A 0.9600 . . no
C9 H9B 0.9600 . . no
C9 H9C 0.9600 . . no
C10 H10 0.9800 . . no
C12 H12 0.9300 . . no
C13 H13 0.9300 . . no
C15 H15 0.9300 . . no
C16 H16 0.9300 . . no
C17 H17A 0.9600 . . no
C17 H17B 0.9600 . . no
C17 H17C 0.9600 . . no
C19 H19 0.9300 . . no
C20 H20 0.9300 . . no
C22 H22 0.9300 . . no
C23 H23 0.9300 . . no
C24 H24A 0.9600 . . no
C24 H24B 0.9600 . . no
C24 H24C 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 119.95(14) . . . yes
O1 S1 N4 105.96(12) . . . yes
O1 S1 C18 109.59(15) . . . yes
O2 S1 N4 106.31(11) . . . yes
O2 S1 C18 109.27(14) . . . yes
N4 S1 C18 104.59(12) . . . yes
N2 N1 C10 115.9(2) . . . yes
N1 N2 N3 172.9(3) . . . yes
S1 N4 C5 120.76(16) . . . yes
S1 N4 C7 124.61(17) . . . yes
C5 N4 C7 107.1(2) . . . yes
C2 C1 C6 119.6(3) . . . no
C1 C2 C3 120.1(3) . . . no
C2 C3 C4 122.0(3) . . . no
C3 C4 C5 117.5(3) . . . no
N4 C5 C4 131.6(2) . . . yes
N4 C5 C6 107.9(2) . . . yes
C4 C5 C6 120.4(2) . . . no
C1 C6 C5 120.4(3) . . . no
C1 C6 C8 131.7(3) . . . no
C5 C6 C8 107.9(2) . . . no
N4 C7 C8 108.5(2) . . . yes
N4 C7 C10 122.7(2) . . . yes
C8 C7 C10 128.2(2) . . . no
C6 C8 C7 108.5(2) . . . no
C6 C8 C9 122.3(2) . . . no
C7 C8 C9 129.2(2) . . . no
N1 C10 C7 110.1(2) . . . yes
N1 C10 C11 108.9(2) . . . yes
C7 C10 C11 113.8(2) . . . no
C10 C11 C12 122.0(2) . . . no
C10 C11 C16 119.7(2) . . . no
C12 C11 C16 118.3(2) . . . no
C11 C12 C13 120.3(3) . . . no
C12 C13 C14 122.2(3) . . . no
C13 C14 C15 116.9(3) . . . no
C13 C14 C17 122.2(3) . . . no
C15 C14 C17 121.0(2) . . . no
C14 C15 C16 121.4(3) . . . no
C11 C16 C15 121.0(3) . . . no
S1 C18 C19 119.4(2) . . . yes
S1 C18 C23 120.1(2) . . . yes
C19 C18 C23 120.5(2) . . . no
C18 C19 C20 118.9(3) . . . no
C19 C20 C21 122.0(3) . . . no
C20 C21 C22 117.7(3) . . . no
C20 C21 C24 121.0(3) . . . no
C22 C21 C24 121.3(3) . . . no
C21 C22 C23 121.8(3) . . . no
C18 C23 C22 119.2(3) . . . no
C2 C1 H1 120.00 . . . no
C6 C1 H1 120.00 . . . no
C1 C2 H2 120.00 . . . no
C3 C2 H2 120.00 . . . no
C2 C3 H3 119.00 . . . no
C4 C3 H3 119.00 . . . no
C3 C4 H4 121.00 . . . no
C5 C4 H4 121.00 . . . no
C8 C9 H9A 109.00 . . . no
C8 C9 H9B 110.00 . . . no
C8 C9 H9C 109.00 . . . no
H9A C9 H9B 109.00 . . . no
H9A C9 H9C 109.00 . . . no
H9B C9 H9C 109.00 . . . no
N1 C10 H10 108.00 . . . no
C7 C10 H10 108.00 . . . no
C11 C10 H10 108.00 . . . no
C11 C12 H12 120.00 . . . no
C13 C12 H12 120.00 . . . no
C12 C13 H13 119.00 . . . no
C14 C13 H13 119.00 . . . no
C14 C15 H15 119.00 . . . no
C16 C15 H15 119.00 . . . no
C11 C16 H16 120.00 . . . no
C15 C16 H16 119.00 . . . no
C14 C17 H17A 109.00 . . . no
C14 C17 H17B 110.00 . . . no
C14 C17 H17C 109.00 . . . no
H17A C17 H17B 110.00 . . . no
H17A C17 H17C 109.00 . . . no
H17B C17 H17C 109.00 . . . no
C18 C19 H19 121.00 . . . no
C20 C19 H19 121.00 . . . no
C19 C20 H20 119.00 . . . no
C21 C20 H20 119.00 . . . no
C21 C22 H22 119.00 . . . no
C23 C22 H22 119.00 . . . no
C18 C23 H23 120.00 . . . no
C22 C23 H23 120.00 . . . no
C21 C24 H24A 110.00 . . . no
C21 C24 H24B 110.00 . . . no
C21 C24 H24C 109.00 . . . no
H24A C24 H24B 109.00 . . . no
H24A C24 H24C 109.00 . . . no
H24B C24 H24C 109.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N4 C5 -41.5(2) . . . . no
O2 S1 N4 C5 -170.13(18) . . . . no
C18 S1 N4 C5 74.3(2) . . . . no
O1 S1 N4 C7 172.7(2) . . . . no
O2 S1 N4 C7 44.0(2) . . . . no
C18 S1 N4 C7 -71.5(2) . . . . no
N4 S1 C18 C19 -87.0(3) . . . . no
O1 S1 C18 C19 26.2(3) . . . . no
O2 S1 C18 C19 159.5(2) . . . . no
N4 S1 C18 C23 90.8(2) . . . . no
O1 S1 C18 C23 -156.0(2) . . . . no
O2 S1 C18 C23 -22.7(3) . . . . no
N2 N1 C10 C7 69.0(3) . . . . no
N2 N1 C10 C11 -165.7(2) . . . . no
S1 N4 C5 C4 28.3(4) . . . . no
C7 N4 C5 C4 179.4(3) . . . . no
C7 N4 C5 C6 -3.3(2) . . . . no
C5 N4 C7 C8 3.8(2) . . . . no
C5 N4 C7 C10 175.0(2) . . . . no
S1 N4 C7 C8 153.51(18) . . . . no
S1 N4 C7 C10 -35.3(3) . . . . no
S1 N4 C5 C6 -154.39(16) . . . . no
C6 C1 C2 C3 0.8(5) . . . . no
C2 C1 C6 C5 -0.9(4) . . . . no
C2 C1 C6 C8 -179.4(3) . . . . no
C1 C2 C3 C4 -0.3(5) . . . . no
C2 C3 C4 C5 -0.2(5) . . . . no
C3 C4 C5 C6 0.1(4) . . . . no
C3 C4 C5 N4 177.1(3) . . . . no
N4 C5 C6 C8 1.6(2) . . . . no
C4 C5 C6 C1 0.5(4) . . . . no
N4 C5 C6 C1 -177.2(2) . . . . no
C4 C5 C6 C8 179.3(2) . . . . no
C5 C6 C8 C7 0.8(2) . . . . no
C5 C6 C8 C9 -177.9(2) . . . . no
C1 C6 C8 C7 179.4(3) . . . . no
C1 C6 C8 C9 0.8(4) . . . . no
N4 C7 C8 C9 175.7(2) . . . . no
C10 C7 C8 C6 -173.4(2) . . . . no
N4 C7 C8 C6 -2.8(2) . . . . no
N4 C7 C10 N1 -88.1(3) . . . . no
N4 C7 C10 C11 149.4(2) . . . . no
C8 C7 C10 N1 81.3(3) . . . . no
C8 C7 C10 C11 -41.2(4) . . . . no
C10 C7 C8 C9 5.1(4) . . . . no
N1 C10 C11 C12 7.2(3) . . . . no
N1 C10 C11 C16 -175.4(2) . . . . no
C7 C10 C11 C16 -52.3(3) . . . . no
C7 C10 C11 C12 130.3(3) . . . . no
C10 C11 C16 C15 -177.7(2) . . . . no
C16 C11 C12 C13 0.2(4) . . . . no
C10 C11 C12 C13 177.7(3) . . . . no
C12 C11 C16 C15 -0.2(4) . . . . no
C11 C12 C13 C14 0.0(5) . . . . no
C12 C13 C14 C15 -0.3(4) . . . . no
C12 C13 C14 C17 -179.5(3) . . . . no
C17 C14 C15 C16 179.6(3) . . . . no
C13 C14 C15 C16 0.4(4) . . . . no
C14 C15 C16 C11 -0.2(4) . . . . no
S1 C18 C19 C20 177.2(2) . . . . no
C23 C18 C19 C20 -0.6(5) . . . . no
S1 C18 C23 C22 -176.5(2) . . . . no
C19 C18 C23 C22 1.3(4) . . . . no
C18 C19 C20 C21 0.1(5) . . . . no
C19 C20 C21 C22 -0.3(5) . . . . no
C19 C20 C21 C24 -180.0(3) . . . . no
C20 C21 C22 C23 1.0(5) . . . . no
C24 C21 C22 C23 -179.3(3) . . . . no
C21 C22 C23 C18 -1.6(5) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S1 H4 3.0700 . . no
S1 H10 2.8300 . . no
O1 C4 2.911(4) . . no
O2 C1 3.393(4) . 1_455 no
O2 C10 2.911(3) . . no
O2 N2 3.175(3) . . no
O1 H4 2.3300 . . no
O1 H19 2.6300 . . no
O2 H1 2.7400 . 1_455 no
O2 H10 2.1500 . . no
O2 H23 2.6200 . . no
O2 H17C 2.7700 . 2_655 no
N2 O2 3.175(3) . . no
N2 N4 3.289(3) . . no
N4 N2 3.289(3) . . no
N1 H12 2.3600 . . no
N3 H9A 2.9400 . 1_455 no
C1 O2 3.393(4) . 1_655 no
C4 O1 2.911(4) . . no
C5 C24 3.564(4) . 1_556 no
C5 C19 3.596(4) . . no
C6 C24 3.515(4) . 1_556 no
C8 C16 3.400(4) . . no
C9 C11 3.126(4) . . no
C9 C16 3.398(4) . . no
C10 O2 2.911(3) . . no
C11 C9 3.126(4) . . no
C13 C23 3.511(4) . 2_645 no
C16 C9 3.398(4) . . no
C16 C8 3.400(4) . . no
C19 C5 3.596(4) . . no
C23 C13 3.511(4) . 2_655 no
C24 C5 3.564(4) . 1_554 no
C24 C6 3.515(4) . 1_554 no
C1 H9A 2.7600 . . no
C2 H9C 2.8000 . 2_756 no
C3 H17A 3.0300 . 1_565 no
C3 H9C 2.8200 . 2_756 no
C5 H24C 3.0200 . 1_556 no
C7 H16 2.8100 . . no
C9 H20 2.9900 . 2_745 no
C9 H1 2.9500 . . no
C11 H9B 2.7200 . . no
C16 H9B 2.7100 . . no
C23 H16 2.9300 . . no
H1 O2 2.7400 . 1_655 no
H1 C9 2.9500 . . no
H1 H9A 2.2900 . . no
H3 H13 2.4200 . 1_565 no
H4 S1 3.0700 . . no
H4 O1 2.3300 . . no
H9A N3 2.9400 . 1_655 no
H9A C1 2.7600 . . no
H9A H1 2.2900 . . no
H9B C11 2.7200 . . no
H9B C16 2.7100 . . no
H9B H20 2.3100 . 2_745 no
H9C C2 2.8000 . 2_746 no
H9C C3 2.8200 . 2_746 no
H10 S1 2.8300 . . no
H10 O2 2.1500 . . no
H10 H23 2.5800 . . no
H12 N1 2.3600 . . no
H13 H3 2.4200 . 1_545 no
H13 H17A 2.3700 . . no
H16 C7 2.8100 . . no
H16 C23 2.9300 . . no
H17A C3 3.0300 . 1_545 no
H17A H13 2.3700 . . no
H17C O2 2.7700 . 2_645 no
H19 O1 2.6300 . . no
H20 C9 2.9900 . 2_755 no
H20 H9B 2.3100 . 2_755 no
H22 H24A 2.3500 . . no
H23 O2 2.6200 . . no
H23 H10 2.5800 . . no
H24A H22 2.3500 . . no
H24C C5 3.0200 . 1_554 no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C4 H4 O1 0.9300 2.3300 2.911(4) 120.00 . yes
C10 H10 O2 0.9800 2.1500 2.911(3) 133.00 . yes
C12 H12 N1 0.9300 2.3600 2.742(4) 104.00 . yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END
