# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_megr222f8
#TrackingRef 'JOQ_JCampos.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N5 O S'
_chemical_formula_weight         327.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   11.4055(9)
_cell_length_b                   12.3528(9)
_cell_length_c                   11.3243(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.230(4)
_cell_angle_gamma                90.00
_cell_volume                     1559.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      3.966
_cell_measurement_theta_max      66.022

_exptl_crystal_description       block
_exptl_crystal_colour            colourles
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    1.947
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8000
_exptl_absorpt_correction_T_max  0.8598
_exptl_absorpt_process_details   'Bruker SADABS, 2010'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_monochromator  'graded multilayer optics'
_diffrn_measurement_device_type  'Bruker X8 Proteum'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19567
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.97
_diffrn_reflns_theta_max         66.38
_reflns_number_total             2710
_reflns_number_gt                2365
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0938P)²+0.7908P] 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         2710
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1586
_refine_ls_wR_factor_gt          0.1532
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.66239(19) 0.96349(16) 0.07835(16) 0.0439(5) Uani 1 1 d . . .
C2 C 0.6662(2) 0.86136(18) 0.0500(2) 0.0437(6) Uani 1 1 d . . .
H2 H 0.6772 0.8119 0.1133 0.052 Uiso 1 1 calc R . .
N3 N 0.65581(17) 0.82074(14) -0.06182(16) 0.0392(4) Uani 1 1 d . . .
C4 C 0.6359(2) 0.89426(17) -0.15489(19) 0.0367(5) Uani 1 1 d . . .
C5 C 0.6262(2) 1.00513(17) -0.13212(19) 0.0379(5) Uani 1 1 d . . .
C6 C 0.6440(2) 1.04053(17) -0.0114(2) 0.0384(5) Uani 1 1 d . . .
N6 N 0.6441(2) 1.14345(15) 0.02605(17) 0.0464(5) Uani 1 1 d . . .
N7 N 0.5974(2) 1.05668(16) -0.24328(17) 0.0481(5) Uani 1 1 d . . .
C8 C 0.5940(3) 0.9748(2) -0.3197(2) 0.0519(6) Uani 1 1 d . . .
H8 H 0.5761 0.9864 -0.4028 0.062 Uiso 1 1 calc R . .
N9 N 0.6173(2) 0.87298(16) -0.27360(17) 0.0458(5) Uani 1 1 d . . .
C10 C 0.6616(3) 1.1695(2) 0.1540(2) 0.0529(6) Uani 1 1 d . . .
H10A H 0.6152 1.1208 0.1918 0.079 Uiso 1 1 calc R . .
H10B H 0.6361 1.2426 0.1630 0.079 Uiso 1 1 calc R . .
H10C H 0.7450 1.1624 0.1915 0.079 Uiso 1 1 calc R . .
C11 C 0.6398(4) 1.2341(2) -0.0571(3) 0.0701(9) Uani 1 1 d . . .
H11A H 0.6388 1.2072 -0.1369 0.105 Uiso 1 1 calc R . .
H11B H 0.7092 1.2791 -0.0312 0.105 Uiso 1 1 calc R . .
H11C H 0.5686 1.2759 -0.0582 0.105 Uiso 1 1 calc R . .
C12 C 0.6699(2) 0.70468(18) -0.0818(2) 0.0446(6) Uani 1 1 d . . .
H12A H 0.6079 0.6814 -0.1496 0.054 Uiso 1 1 calc R . .
H12B H 0.6590 0.6652 -0.0109 0.054 Uiso 1 1 calc R . .
C13 C 0.7921(2) 0.67696(19) -0.1073(2) 0.0469(6) Uani 1 1 d . . .
H13 H 0.7977 0.7107 -0.1843 0.056 Uiso 1 1 calc R . .
S14 S 0.91662(6) 0.72618(5) 0.00769(7) 0.0582(3) Uani 1 1 d . . .
C15 C 0.9220(2) 0.62347(19) 0.1167(2) 0.0446(6) Uani 1 1 d . . .
C16 C 0.9889(3) 0.6413(2) 0.2330(3) 0.0582(7) Uani 1 1 d . . .
H16 H 1.0278 0.7073 0.2511 0.070 Uiso 1 1 calc R . .
C17 C 0.9989(3) 0.5641(3) 0.3213(3) 0.0710(9) Uani 1 1 d . . .
H17 H 1.0459 0.5769 0.3978 0.085 Uiso 1 1 calc R . .
C18 C 0.9389(3) 0.4673(3) 0.2962(3) 0.0721(9) Uani 1 1 d . . .
H18 H 0.9440 0.4151 0.3562 0.087 Uiso 1 1 calc R . .
C19 C 0.8714(3) 0.4480(2) 0.1823(3) 0.0629(8) Uani 1 1 d . . .
H19 H 0.8309 0.3826 0.1661 0.076 Uiso 1 1 calc R . .
C20 C 0.8629(2) 0.52474(19) 0.0911(2) 0.0456(6) Uani 1 1 d . . .
O21 O 0.78941(18) 0.49834(13) -0.01994(18) 0.0615(5) Uani 1 1 d . . .
C22 C 0.8047(3) 0.5547(2) -0.1206(3) 0.0613(8) Uani 1 1 d . . .
H22A H 0.7457 0.5301 -0.1901 0.074 Uiso 1 1 calc R . .
H22B H 0.8836 0.5389 -0.1354 0.074 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
N1 C2 1.305(3) . ?
N1 C6 1.376(3) . ?
C2 N3 1.344(3) . ?
C2 H2 0.9300 . ?
N3 C4 1.373(3) . ?
N3 C12 1.466(3) . ?
C4 N9 1.342(3) . ?
C4 C5 1.402(3) . ?
C5 N7 1.387(3) . ?
C5 C6 1.408(3) . ?
C6 N6 1.340(3) . ?
N6 C10 1.456(3) . ?
N6 C11 1.458(3) . ?
N7 C8 1.327(3) . ?
C8 N9 1.366(3) . ?
C8 H8 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.522(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C22 1.527(4) . ?
C13 S14 1.816(3) . ?
C13 H13 0.9800 . ?
S14 C15 1.762(3) . ?
C15 C16 1.393(4) . ?
C15 C20 1.394(3) . ?
C16 C17 1.369(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.376(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.390(4) . ?
C19 H19 0.9300 . ?
C20 O21 1.395(3) . ?
O21 C22 1.377(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?

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
C2 N1 C6 119.65(19) . . ?
N1 C2 N3 126.3(2) . . ?
N1 C2 H2 116.8 . . ?
N3 C2 H2 116.8 . . ?
C2 N3 C4 116.33(18) . . ?
C2 N3 C12 121.34(19) . . ?
C4 N3 C12 122.29(19) . . ?
N9 C4 N3 127.2(2) . . ?
N9 C4 C5 111.94(19) . . ?
N3 C4 C5 120.76(19) . . ?
N7 C5 C4 107.12(18) . . ?
N7 C5 C6 134.1(2) . . ?
C4 C5 C6 118.75(19) . . ?
N6 C6 N1 115.61(19) . . ?
N6 C6 C5 126.3(2) . . ?
N1 C6 C5 118.07(19) . . ?
C6 N6 C10 121.1(2) . . ?
C6 N6 C11 121.8(2) . . ?
C10 N6 C11 116.9(2) . . ?
C8 N7 C5 102.18(19) . . ?
N7 C8 N9 118.4(2) . . ?
N7 C8 H8 120.8 . . ?
N9 C8 H8 120.8 . . ?
C4 N9 C8 100.33(18) . . ?
N6 C10 H10A 109.5 . . ?
N6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N6 C11 H11A 109.5 . . ?
N6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C13 112.58(19) . . ?
N3 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
N3 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 C22 110.5(2) . . ?
C12 C13 S14 113.42(17) . . ?
C22 C13 S14 109.04(17) . . ?
C12 C13 H13 107.9 . . ?
C22 C13 H13 107.9 . . ?
S14 C13 H13 107.9 . . ?
C15 S14 C13 99.63(11) . . ?
C16 C15 C20 118.6(2) . . ?
C16 C15 S14 118.7(2) . . ?
C20 C15 S14 122.73(19) . . ?
C17 C16 C15 121.7(3) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 119.5(3) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C15 119.2(2) . . ?
C19 C20 O21 116.4(2) . . ?
C15 C20 O21 124.3(2) . . ?
C22 O21 C20 118.1(2) . . ?
O21 C22 C13 112.8(2) . . ?
O21 C22 H22A 109.0 . . ?
C13 C22 H22A 109.0 . . ?
O21 C22 H22B 109.0 . . ?
C13 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        66.38
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.058



_database_code_depnum_ccdc_archive 'CCDC 864711'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_megr88
#TrackingRef 'JOQ_JCampos.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 Cl N5 O S'
_chemical_formula_weight         347.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   5.0547(4)
_cell_length_b                   13.3237(10)
_cell_length_c                   23.2593(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1566.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7646
_cell_measurement_theta_min      3.801
_cell_measurement_theta_max      64.608

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    3.508
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7205
_exptl_absorpt_correction_T_max  0.7667
_exptl_absorpt_process_details   'Bruker SADABS, 2010'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_monochromator  'graded multilayer optics'
_diffrn_measurement_device_type  'Bruker X8 Proteum'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19523
_diffrn_reflns_av_R_equivalents  0.0763
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.80
_diffrn_reflns_theta_max         66.41
_reflns_number_total             2706
_reflns_number_gt                2259
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0657P)²+0.8607P] 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, 1098 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_number_reflns         2706
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1236
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.4872(7) 0.4025(2) -0.15676(14) 0.0435(8) Uani 1 1 d . . .
C2 C -0.4170(9) 0.4950(3) -0.14167(17) 0.0428(9) Uani 1 1 d . . .
Cl2 Cl -0.5957(3) 0.58920(8) -0.17513(5) 0.0624(3) Uani 1 1 d . . .
N3 N -0.2356(7) 0.5270(3) -0.10509(14) 0.0440(8) Uani 1 1 d . . .
C5 C -0.1574(8) 0.3468(3) -0.09195(16) 0.0399(9) Uani 1 1 d . . .
C4 C -0.1096(8) 0.4472(3) -0.08131(16) 0.0412(9) Uani 1 1 d . . .
N6 N -0.4261(7) 0.2311(3) -0.14627(16) 0.0523(9) Uani 1 1 d . . .
H6 H -0.3354 0.1820 -0.1325 0.063 Uiso 1 1 calc R . .
C6 C -0.3574(8) 0.3246(3) -0.13174(16) 0.0410(9) Uani 1 1 d . . .
N7 N 0.0110(7) 0.2869(3) -0.05888(15) 0.0485(8) Uani 1 1 d . . .
C8 C 0.1542(9) 0.3526(3) -0.02982(18) 0.0484(10) Uani 1 1 d . . .
H8 H 0.2853 0.3340 -0.0039 0.058 Uiso 1 1 calc R . .
N9 N 0.0919(7) 0.4510(2) -0.04145(14) 0.0434(8) Uani 1 1 d . . .
C10 C -0.6460(10) 0.2084(4) -0.1841(2) 0.0625(12) Uani 1 1 d . . .
H10A H -0.6265 0.2451 -0.2193 0.094 Uiso 1 1 calc R . .
H10B H -0.8088 0.2273 -0.1658 0.094 Uiso 1 1 calc R . .
H10C H -0.6485 0.1377 -0.1922 0.094 Uiso 1 1 calc R . .
C12 C -0.0063(8) 0.5894(3) 0.02574(18) 0.0462(10) Uani 1 1 d . . .
H12 H -0.1596 0.6087 0.0024 0.055 Uiso 1 1 calc R . .
C11 C 0.1966(9) 0.5409(3) -0.01438(18) 0.0482(11) Uani 1 1 d . . .
H11A H 0.2471 0.5887 -0.0439 0.058 Uiso 1 1 calc R . .
H11B H 0.3539 0.5238 0.0074 0.058 Uiso 1 1 calc R . .
S13 S 0.1261(3) 0.70259(8) 0.05795(5) 0.0566(3) Uani 1 1 d . . .
C14 C 0.2788(8) 0.6516(3) 0.11956(17) 0.0424(9) Uani 1 1 d . . .
C15 C 0.4383(10) 0.7146(4) 0.1523(2) 0.0591(12) Uani 1 1 d . . .
H15 H 0.4605 0.7810 0.1410 0.071 Uiso 1 1 calc R . .
C16 C 0.5638(11) 0.6809(4) 0.2010(2) 0.0709(15) Uani 1 1 d . . .
H16 H 0.6670 0.7245 0.2227 0.085 Uiso 1 1 calc R . .
C17 C 0.5359(10) 0.5822(4) 0.2176(2) 0.0666(14) Uani 1 1 d . . .
H17 H 0.6246 0.5587 0.2499 0.080 Uiso 1 1 calc R . .
C18 C 0.3777(10) 0.5182(4) 0.18644(18) 0.0549(11) Uani 1 1 d . . .
H18 H 0.3547 0.4521 0.1982 0.066 Uiso 1 1 calc R . .
C19 C 0.2526(8) 0.5534(3) 0.13734(18) 0.0436(10) Uani 1 1 d . . .
O20 O 0.1106(6) 0.4815(2) 0.10657(12) 0.0493(7) Uani 1 1 d . . .
C21 C -0.1032(9) 0.5200(3) 0.07241(17) 0.0482(10) Uani 1 1 d . . .
H21A H -0.2256 0.5560 0.0971 0.058 Uiso 1 1 calc R . .
H21B H -0.1982 0.4644 0.0551 0.058 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
N1 C2 1.329(5) . ?
N1 C6 1.359(5) . ?
C2 N3 1.321(5) . ?
C2 Cl2 1.731(4) . ?
N3 C4 1.357(5) . ?
C5 C4 1.381(5) . ?
C5 N7 1.398(5) . ?
C5 C6 1.402(5) . ?
C4 N9 1.378(5) . ?
N6 C6 1.338(5) . ?
N6 C10 1.449(6) . ?
N6 H6 0.8600 . ?
N7 C8 1.322(6) . ?
C8 N9 1.374(5) . ?
C8 H8 0.9300 . ?
N9 C11 1.454(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 C21 1.508(6) . ?
C12 C11 1.530(6) . ?
C12 S13 1.812(4) . ?
C12 H12 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
S13 C14 1.764(4) . ?
C14 C19 1.379(6) . ?
C14 C15 1.391(6) . ?
C15 C16 1.373(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(6) . ?
C18 H18 0.9300 . ?
C19 O20 1.395(5) . ?
O20 C21 1.436(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?

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
C2 N1 C6 117.8(3) . . ?
N3 C2 N1 130.8(4) . . ?
N3 C2 Cl2 114.7(3) . . ?
N1 C2 Cl2 114.4(3) . . ?
C2 N3 C4 109.6(3) . . ?
C4 C5 N7 110.3(3) . . ?
C4 C5 C6 116.7(3) . . ?
N7 C5 C6 133.0(4) . . ?
N3 C4 N9 126.3(4) . . ?
N3 C4 C5 127.1(4) . . ?
N9 C4 C5 106.6(3) . . ?
C6 N6 C10 123.1(4) . . ?
C6 N6 H6 118.4 . . ?
C10 N6 H6 118.4 . . ?
N6 C6 N1 118.6(4) . . ?
N6 C6 C5 123.4(4) . . ?
N1 C6 C5 118.0(3) . . ?
C8 N7 C5 103.7(3) . . ?
N7 C8 N9 113.9(4) . . ?
N7 C8 H8 123.1 . . ?
N9 C8 H8 123.1 . . ?
C8 N9 C4 105.5(3) . . ?
C8 N9 C11 128.1(4) . . ?
C4 N9 C11 126.2(3) . . ?
N6 C10 H10A 109.5 . . ?
N6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C21 C12 C11 113.4(4) . . ?
C21 C12 S13 109.4(3) . . ?
C11 C12 S13 110.8(3) . . ?
C21 C12 H12 107.6 . . ?
C11 C12 H12 107.6 . . ?
S13 C12 H12 107.6 . . ?
N9 C11 C12 111.6(3) . . ?
N9 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N9 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C14 S13 C12 100.19(19) . . ?
C19 C14 C15 117.6(4) . . ?
C19 C14 S13 124.6(3) . . ?
C15 C14 S13 117.8(3) . . ?
C16 C15 C14 121.5(5) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 119.7(5) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 120.3(5) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.3(4) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C14 C19 C18 121.6(4) . . ?
C14 C19 O20 123.2(4) . . ?
C18 C19 O20 115.2(4) . . ?
C19 O20 C21 115.2(3) . . ?
O20 C21 C12 111.9(3) . . ?
O20 C21 H21A 109.2 . . ?
C12 C21 H21A 109.2 . . ?
O20 C21 H21B 109.2 . . ?
C12 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        66.41
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 864709'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_megr231
#TrackingRef 'JOQ_JCampos.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 N5 O S'
_chemical_formula_weight         313.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Cc

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'

_cell_length_a                   6.530(3)
_cell_length_b                   31.767(16)
_cell_length_c                   14.249(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.555(12)
_cell_angle_gamma                90.00
_cell_volume                     2946(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2300
_cell_measurement_theta_min      27.52
_cell_measurement_theta_max      65.66

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    2.036
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8223
_exptl_absorpt_correction_T_max  0.8876
_exptl_absorpt_process_details   'Bruker SADABS, 2010'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_monochromator  'graded multilayer optics'
_diffrn_measurement_device_type  'Bruker X8 Proteum'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16066
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_sigmaI/netI    0.0618
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         66.45
_reflns_number_total             4471
_reflns_number_gt                3426
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0739P)²+2.5055P] 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   0.47(3)
_refine_ls_number_reflns         4471
_refine_ls_number_parameters     400
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1637
_refine_ls_wR_factor_gt          0.1371
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.087
_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
N1 N 0.3396(7) 0.55444(15) 0.9336(3) 0.0609(11) Uani 1 1 d . . .
C2 C 0.1627(9) 0.5330(2) 0.9227(4) 0.0676(15) Uani 1 1 d . . .
H2 H 0.0780 0.5359 0.9718 0.081 Uiso 1 1 calc R . .
N3 N 0.0894(7) 0.50831(15) 0.8534(3) 0.0602(11) Uani 1 1 d . . .
C4 C 0.2248(7) 0.50612(15) 0.7880(4) 0.0497(11) Uani 1 1 d . . .
C5 C 0.4108(8) 0.52737(15) 0.7866(4) 0.0521(12) Uani 1 1 d . . .
N6 N 0.6443(7) 0.57425(15) 0.8731(3) 0.0626(11) Uani 1 1 d . . .
H6 H 0.7234 0.5738 0.8276 0.075 Uiso 1 1 calc R . .
C6 C 0.4697(8) 0.55201(16) 0.8648(4) 0.0522(12) Uani 1 1 d . . .
N7 N 0.5050(7) 0.51670(15) 0.7058(3) 0.0646(12) Uani 1 1 d . . .
C8 C 0.3774(9) 0.48983(17) 0.6630(4) 0.0617(14) Uani 1 1 d . . .
H8 H 0.4021 0.4767 0.6066 0.074 Uiso 1 1 calc R . .
N9 N 0.2059(6) 0.48286(13) 0.7084(3) 0.0519(10) Uani 1 1 d . . .
C10 C 0.7036(11) 0.5987(2) 0.9552(5) 0.0787(18) Uani 1 1 d . . .
H10A H 0.8401 0.6094 0.9509 0.118 Uiso 1 1 calc R . .
H10B H 0.7007 0.5813 1.0102 0.118 Uiso 1 1 calc R . .
H10C H 0.6099 0.6218 0.9594 0.118 Uiso 1 1 calc R . .
C11 C 0.0467(8) 0.45113(17) 0.6896(4) 0.0577(13) Uani 1 1 d . . .
H11A H 0.0565 0.4397 0.6270 0.069 Uiso 1 1 calc R . .
H11B H -0.0872 0.4642 0.6912 0.069 Uiso 1 1 calc R . .
C12 C 0.0661(8) 0.41584(16) 0.7606(4) 0.0558(12) Uani 1 1 d . . .
H12 H 0.0716 0.4286 0.8234 0.067 Uiso 1 1 calc R . .
S13 S 0.3024(2) 0.38608(5) 0.75272(12) 0.0697(4) Uani 1 1 d . . .
C14 C 0.2219(8) 0.35194(15) 0.6614(4) 0.0533(12) Uani 1 1 d . . .
C15 C 0.3684(9) 0.32911(18) 0.6176(5) 0.0669(15) Uani 1 1 d . . .
H15 H 0.5062 0.3326 0.6379 0.080 Uiso 1 1 calc R . .
C16 C 0.3175(12) 0.3017(2) 0.5461(5) 0.0791(18) Uani 1 1 d . . .
H16 H 0.4192 0.2868 0.5182 0.095 Uiso 1 1 calc R . .
C17 C 0.1141(12) 0.2963(2) 0.5153(5) 0.0777(18) Uani 1 1 d . . .
H17 H 0.0780 0.2781 0.4657 0.093 Uiso 1 1 calc R . .
C18 C -0.0354(10) 0.31781(17) 0.5579(4) 0.0656(15) Uani 1 1 d . . .
H18 H -0.1729 0.3135 0.5381 0.079 Uiso 1 1 calc R . .
C19 C 0.0170(8) 0.34602(15) 0.6305(4) 0.0542(12) Uani 1 1 d . . .
O20 O -0.1444(5) 0.36728(11) 0.6641(3) 0.0639(10) Uani 1 1 d . . .
C21 C -0.1130(9) 0.38589(17) 0.7528(4) 0.0612(14) Uani 1 1 d . . .
H21A H -0.0898 0.3640 0.7998 0.073 Uiso 1 1 calc R . .
H21B H -0.2363 0.4010 0.7663 0.073 Uiso 1 1 calc R . .
N31 N 0.0992(7) 0.57840(15) 0.5078(3) 0.0655(12) Uani 1 1 d . . .
C32 C 0.2737(9) 0.60110(19) 0.5148(5) 0.0708(16) Uani 1 1 d . . .
H32 H 0.3458 0.6016 0.4611 0.085 Uiso 1 1 calc R . .
N33 N 0.3579(7) 0.62291(15) 0.5875(4) 0.0648(12) Uani 1 1 d . . .
C34 C 0.2398(8) 0.62046(15) 0.6583(4) 0.0503(11) Uani 1 1 d . . .
C35 C 0.0559(8) 0.59921(16) 0.6635(4) 0.0523(11) Uani 1 1 d . . .
C36 C -0.0142(8) 0.57645(16) 0.5820(4) 0.0530(12) Uani 1 1 d . . .
N36 N -0.1873(7) 0.55461(15) 0.5771(4) 0.0653(12) Uani 1 1 d . . .
H36 H -0.2523 0.5522 0.6270 0.078 Uiso 1 1 calc R . .
N37 N -0.0232(8) 0.60585(15) 0.7495(3) 0.0653(12) Uani 1 1 d . . .
C38 C 0.1143(8) 0.63036(18) 0.7936(4) 0.0620(14) Uani 1 1 d . . .
H38 H 0.1020 0.6401 0.8544 0.074 Uiso 1 1 calc R . .
N39 N 0.2755(6) 0.64035(13) 0.7438(3) 0.0543(10) Uani 1 1 d . . .
C40 C -0.2722(10) 0.5345(2) 0.4915(5) 0.086(2) Uani 1 1 d . . .
H40A H -0.3027 0.5555 0.4439 0.128 Uiso 1 1 calc R . .
H40B H -0.3959 0.5199 0.5036 0.128 Uiso 1 1 calc R . .
H40C H -0.1742 0.5149 0.4701 0.128 Uiso 1 1 calc R . .
C41 C 0.4488(9) 0.66727(16) 0.7712(4) 0.0629(14) Uani 1 1 d . . .
H41A H 0.5744 0.6515 0.7651 0.075 Uiso 1 1 calc R . .
H41B H 0.4443 0.6746 0.8372 0.075 Uiso 1 1 calc R . .
C42 C 0.4573(8) 0.70748(17) 0.7147(4) 0.0583(13) Uani 1 1 d . . .
H42 H 0.4638 0.6995 0.6485 0.070 Uiso 1 1 calc R . .
S43 S 0.2298(2) 0.73959(5) 0.72236(12) 0.0694(4) Uani 1 1 d . . .
C44 C 0.3046(9) 0.76916(16) 0.8234(4) 0.0611(14) Uani 1 1 d . . .
C45 C 0.1561(10) 0.79433(19) 0.8623(5) 0.0743(16) Uani 1 1 d . . .
H45 H 0.0234 0.7954 0.8334 0.089 Uiso 1 1 calc R . .
C46 C 0.2038(14) 0.8170(2) 0.9415(6) 0.089(2) Uani 1 1 d . . .
H46 H 0.1038 0.8335 0.9666 0.106 Uiso 1 1 calc R . .
C47 C 0.3996(16) 0.8159(2) 0.9852(6) 0.097(2) Uani 1 1 d . . .
H47 H 0.4309 0.8311 1.0403 0.117 Uiso 1 1 calc R . .
C48 C 0.5488(12) 0.79221(19) 0.9472(5) 0.0794(18) Uani 1 1 d . . .
H48 H 0.6814 0.7919 0.9763 0.095 Uiso 1 1 calc R . .
C49 C 0.5046(9) 0.76883(17) 0.8662(4) 0.0641(14) Uani 1 1 d . . .
O50 O 0.6610(6) 0.74402(13) 0.8369(3) 0.0729(12) Uani 1 1 d . . .
C51 C 0.6463(8) 0.73329(19) 0.7432(5) 0.0703(17) Uani 1 1 d . . .
H51A H 0.7674 0.7174 0.7298 0.084 Uiso 1 1 calc R . .
H51B H 0.6436 0.7588 0.7056 0.084 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
N1 C2 1.340(8) . ?
N1 C6 1.350(7) . ?
C2 N3 1.320(7) . ?
C2 H2 0.9300 . ?
N3 C4 1.336(7) . ?
C4 N9 1.350(7) . ?
C4 C5 1.391(7) . ?
C5 N7 1.389(7) . ?
C5 C6 1.391(7) . ?
N6 C6 1.338(7) . ?
N6 C10 1.432(7) . ?
N6 H6 0.8600 . ?
N7 C8 1.309(7) . ?
C8 N9 1.355(7) . ?
C8 H8 0.9300 . ?
N9 C11 1.458(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.509(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C21 1.505(7) . ?
C12 S13 1.821(6) . ?
C12 H12 0.9800 . ?
S13 C14 1.743(5) . ?
C14 C15 1.387(8) . ?
C14 C19 1.388(7) . ?
C15 C16 1.361(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.391(8) . ?
C18 H18 0.9300 . ?
C19 O20 1.370(7) . ?
O20 C21 1.395(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
N31 C36 1.339(7) . ?
N31 C32 1.346(7) . ?
C32 N33 1.328(8) . ?
C32 H32 0.9300 . ?
N33 C34 1.320(7) . ?
C34 N39 1.375(7) . ?
C34 C35 1.384(7) . ?
C35 N37 1.383(7) . ?
C35 C36 1.413(7) . ?
C36 N36 1.323(7) . ?
N36 C40 1.447(7) . ?
N36 H36 0.8600 . ?
N37 C38 1.311(7) . ?
C38 N39 1.354(7) . ?
C38 H38 0.9300 . ?
N39 C41 1.447(7) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 C42 1.514(7) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C51 1.510(8) . ?
C42 S43 1.813(6) . ?
C42 H42 0.9800 . ?
S43 C44 1.755(6) . ?
C44 C49 1.397(8) . ?
C44 C45 1.405(9) . ?
C45 C46 1.355(10) . ?
C45 H45 0.9300 . ?
C46 C47 1.377(13) . ?
C46 H46 0.9300 . ?
C47 C48 1.375(11) . ?
C47 H47 0.9300 . ?
C48 C49 1.384(9) . ?
C48 H48 0.9300 . ?
C49 O50 1.380(8) . ?
O50 C51 1.374(8) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?

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
C2 N1 C6 118.2(5) . . ?
N3 C2 N1 130.3(6) . . ?
N3 C2 H2 114.9 . . ?
N1 C2 H2 114.9 . . ?
C2 N3 C4 109.4(5) . . ?
N3 C4 N9 126.3(4) . . ?
N3 C4 C5 127.7(5) . . ?
N9 C4 C5 105.9(4) . . ?
N7 C5 C6 133.5(5) . . ?
N7 C5 C4 109.8(4) . . ?
C6 C5 C4 116.6(5) . . ?
C6 N6 C10 122.1(6) . . ?
C6 N6 H6 118.9 . . ?
C10 N6 H6 118.9 . . ?
N6 C6 N1 119.1(5) . . ?
N6 C6 C5 123.2(5) . . ?
N1 C6 C5 117.7(5) . . ?
C8 N7 C5 103.7(5) . . ?
N7 C8 N9 113.8(5) . . ?
N7 C8 H8 123.1 . . ?
N9 C8 H8 123.1 . . ?
C4 N9 C8 106.7(4) . . ?
C4 N9 C11 123.3(4) . . ?
C8 N9 C11 129.0(5) . . ?
N6 C10 H10A 109.5 . . ?
N6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N9 C11 C12 111.7(4) . . ?
N9 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N9 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C21 C12 C11 113.3(4) . . ?
C21 C12 S13 108.9(4) . . ?
C11 C12 S13 111.8(4) . . ?
C21 C12 H12 107.5 . . ?
C11 C12 H12 107.5 . . ?
S13 C12 H12 107.5 . . ?
C14 S13 C12 99.3(2) . . ?
C15 C14 C19 117.9(5) . . ?
C15 C14 S13 118.9(4) . . ?
C19 C14 S13 123.2(4) . . ?
C16 C15 C14 122.3(6) . . ?
C16 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C15 C16 C17 119.4(6) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 120.0(6) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.5(6) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
O20 C19 C14 124.9(5) . . ?
O20 C19 C18 115.3(5) . . ?
C14 C19 C18 119.8(5) . . ?
C19 O20 C21 117.6(4) . . ?
O20 C21 C12 113.1(5) . . ?
O20 C21 H21A 109.0 . . ?
C12 C21 H21A 109.0 . . ?
O20 C21 H21B 109.0 . . ?
C12 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C36 N31 C32 119.0(5) . . ?
N33 C32 N31 129.3(6) . . ?
N33 C32 H32 115.4 . . ?
N31 C32 H32 115.4 . . ?
C34 N33 C32 109.6(5) . . ?
N33 C34 N39 125.5(4) . . ?
N33 C34 C35 129.1(5) . . ?
N39 C34 C35 105.3(5) . . ?
N37 C35 C34 111.1(5) . . ?
N37 C35 C36 133.4(5) . . ?
C34 C35 C36 115.6(5) . . ?
N36 C36 N31 120.4(5) . . ?
N36 C36 C35 122.1(5) . . ?
N31 C36 C35 117.5(4) . . ?
C36 N36 C40 123.0(5) . . ?
C36 N36 H36 118.5 . . ?
C40 N36 H36 118.5 . . ?
C38 N37 C35 103.0(5) . . ?
N37 C38 N39 114.8(5) . . ?
N37 C38 H38 122.6 . . ?
N39 C38 H38 122.6 . . ?
C38 N39 C34 105.8(4) . . ?
C38 N39 C41 128.4(5) . . ?
C34 N39 C41 125.8(5) . . ?
N36 C40 H40A 109.5 . . ?
N36 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
N36 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
N39 C41 C42 114.5(4) . . ?
N39 C41 H41A 108.6 . . ?
C42 C41 H41A 108.6 . . ?
N39 C41 H41B 108.6 . . ?
C42 C41 H41B 108.6 . . ?
H41A C41 H41B 107.6 . . ?
C51 C42 C41 112.2(5) . . ?
C51 C42 S43 109.5(4) . . ?
C41 C42 S43 112.2(4) . . ?
C51 C42 H42 107.5 . . ?
C41 C42 H42 107.5 . . ?
S43 C42 H42 107.5 . . ?
C44 S43 C42 100.1(3) . . ?
C49 C44 C45 118.8(6) . . ?
C49 C44 S43 122.9(5) . . ?
C45 C44 S43 118.2(5) . . ?
C46 C45 C44 120.8(7) . . ?
C46 C45 H45 119.6 . . ?
C44 C45 H45 119.6 . . ?
C45 C46 C47 120.4(7) . . ?
C45 C46 H46 119.8 . . ?
C47 C46 H46 119.8 . . ?
C48 C47 C46 119.8(7) . . ?
C48 C47 H47 120.1 . . ?
C46 C47 H47 120.1 . . ?
C47 C48 C49 121.0(7) . . ?
C47 C48 H48 119.5 . . ?
C49 C48 H48 119.5 . . ?
O50 C49 C48 116.6(5) . . ?
O50 C49 C44 124.1(5) . . ?
C48 C49 C44 119.1(6) . . ?
C51 O50 C49 116.1(4) . . ?
O50 C51 C42 112.9(5) . . ?
O50 C51 H51A 109.0 . . ?
C42 C51 H51A 109.0 . . ?
O50 C51 H51B 109.0 . . ?
C42 C51 H51B 109.0 . . ?
H51A C51 H51B 107.8 . . ?

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
N36 H36 N7 0.86 2.31 3.072(7) 148.0 1_455
N6 H6 N37 0.86 2.30 3.071(7) 148.8 1_655

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        66.45
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 864710'
