# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013
#######################################################################
#
# 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
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data_adelin3_p1bar
#TrackingRef 'Adelin3_Deposition_5Oct10.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C19 H15 Br N4 S'
_chemical_formula_weight 411.32
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_H-M P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 9.5013(5)
_cell_length_b 10.0576(5)
_cell_length_c 10.2659(5)
_cell_angle_alpha 63.494(2)
_cell_angle_beta 85.295(3)
_cell_angle_gamma 77.804(3)
_cell_volume 858.00(7)
_cell_formula_units_Z 2
_cell_measurement_temperature 150(2)
_cell_measurement_reflns_used 6184
_cell_measurement_theta_min 2.395
_cell_measurement_theta_max 30.138
_exptl_crystal_description 'Rhombic plates'
_exptl_crystal_colour 'Light yellow'
_exptl_crystal_size_max 0.19
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.07
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.592
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 416
_exptl_absorpt_coefficient_mu 2.526
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.6481
_exptl_absorpt_correction_T_max 0.8430
_exptl_absorpt_process_details 'SADABS (Bruker, 2001)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 150(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Kappa APEXII CCD Diffractometer'
_diffrn_measurement_method '\f scans and \w scans with \k offsets'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 12449
_diffrn_reflns_av_R_equivalents 0.0407
_diffrn_reflns_av_sigmaI/netI 0.0336
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.95
_diffrn_reflns_theta_max 25.00
_reflns_number_total 3011
_reflns_number_gt 2609
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 (Bruker, 2007)'
_computing_cell_refinement 'SAINT (Bruker, 2007)'
_computing_data_reduction 'SAINT '
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL-Plus (Sheldrick, 2008)'
_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^)+(0.0308P)^2^+0.2068P] 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 refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3011
_refine_ls_number_parameters 286
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0321
_refine_ls_R_factor_gt 0.0247
_refine_ls_wR_factor_ref 0.0621
_refine_ls_wR_factor_gt 0.0588
_refine_ls_goodness_of_fit_ref 1.064
_refine_ls_restrained_S_all 1.064
_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
Br1 Br 1.19776(2) 1.21384(2) 0.05014(2) 0.02904(10) Uani 1 1 d . . .
S1 S 0.82182(6) 0.67043(7) 0.64358(6) 0.02663(15) Uani 1 1 d . . .
N1 N 0.57077(19) 0.3293(2) 0.64054(18) 0.0232(4) Uani 1 1 d . . .
N2 N 0.75897(18) 0.48081(19) 0.40279(18) 0.0192(4) Uani 1 1 d . . .
N3 N 0.7615(2) 0.5129(2) 0.5179(2) 0.0203(4) Uani 1 1 d . . .
N4 N 0.8991(2) 0.6820(2) 0.3783(2) 0.0210(4) Uani 1 1 d . . .
C1 C 0.6945(2) 0.3755(2) 0.4126(2) 0.0176(4) Uani 1 1 d . . .
C2 C 0.6937(2) 0.3616(2) 0.2735(2) 0.0177(4) Uani 1 1 d . . .
C3 C 0.8084(2) 0.3936(2) 0.1782(2) 0.0218(5) Uani 1 1 d . . .
C4 C 0.8040(3) 0.3926(3) 0.0444(2) 0.0251(5) Uani 1 1 d . . .
C5 C 0.6868(2) 0.3562(2) 0.0054(2) 0.0241(5) Uani 1 1 d . . .
C6 C 0.5731(3) 0.3234(2) 0.0994(2) 0.0249(5) Uani 1 1 d . . .
C7 C 0.5758(2) 0.3271(2) 0.2320(2) 0.0218(5) Uani 1 1 d . . .
C8 C 0.6209(2) 0.2762(2) 0.5424(2) 0.0196(5) Uani 1 1 d . . .
C9 C 0.6072(3) 0.1342(3) 0.5617(2) 0.0267(5) Uani 1 1 d . . .
C10 C 0.5320(3) 0.0481(3) 0.6800(3) 0.0357(6) Uani 1 1 d . . .
C11 C 0.4748(3) 0.1048(3) 0.7765(3) 0.0327(6) Uani 1 1 d . . .
C12 C 0.4986(2) 0.2438(3) 0.7538(2) 0.0280(5) Uani 1 1 d . . .
C13 C 0.8292(2) 0.6248(2) 0.5047(2) 0.0186(4) Uani 1 1 d . . .
C14 C 0.9739(2) 0.8027(2) 0.3159(2) 0.0183(4) Uani 1 1 d . . .
C15 C 0.9594(3) 0.9192(3) 0.3569(2) 0.0256(5) Uani 1 1 d . . .
C16 C 1.0300(3) 1.0382(3) 0.2803(2) 0.0262(5) Uani 1 1 d . . .
C17 C 1.1132(2) 1.0418(2) 0.1628(2) 0.0222(5) Uani 1 1 d . . .
C18 C 1.1312(2) 0.9261(2) 0.1227(2) 0.0224(5) Uani 1 1 d . . .
C19 C 1.0621(2) 0.8062(3) 0.2001(2) 0.0213(5) Uani 1 1 d . . .
H3 H 0.886(2) 0.417(2) 0.206(2) 0.018(6) Uiso 1 1 d . . .
H4 H 0.880(3) 0.420(3) -0.023(3) 0.040(7) Uiso 1 1 d . . .
H5 H 0.683(3) 0.358(3) -0.085(3) 0.034(7) Uiso 1 1 d . . .
H6 H 0.492(3) 0.304(3) 0.072(2) 0.026(6) Uiso 1 1 d . . .
H7 H 0.496(2) 0.314(2) 0.293(2) 0.023(6) Uiso 1 1 d . . .
H9 H 0.646(2) 0.100(3) 0.499(2) 0.020(6) Uiso 1 1 d . . .
H10 H 0.526(3) -0.048(3) 0.692(3) 0.051(8) Uiso 1 1 d . . .
H11 H 0.427(3) 0.055(3) 0.850(3) 0.036(7) Uiso 1 1 d . . .
H12 H 0.463(3) 0.287(3) 0.818(3) 0.028(6) Uiso 1 1 d . . .
H15 H 0.903(3) 0.920(3) 0.429(3) 0.036(7) Uiso 1 1 d . . .
H16 H 1.019(3) 1.117(3) 0.305(3) 0.036(7) Uiso 1 1 d . . .
H18 H 1.185(2) 0.929(3) 0.042(2) 0.026(6) Uiso 1 1 d . . .
H19 H 1.071(2) 0.724(3) 0.177(2) 0.022(6) Uiso 1 1 d . . .
H3N H 0.714(3) 0.479(3) 0.582(3) 0.022(7) Uiso 1 1 d . . .
H4N H 0.890(2) 0.645(3) 0.328(2) 0.021(7) 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
Br1 0.03020(15) 0.02356(14) 0.03275(15) -0.00777(10) 0.00579(10) -0.01677(10)
S1 0.0330(3) 0.0356(3) 0.0207(3) -0.0159(2) 0.0076(2) -0.0206(3)
N1 0.0218(10) 0.0245(10) 0.0199(9) -0.0058(8) 0.0044(8) -0.0085(8)
N2 0.0199(9) 0.0208(9) 0.0191(9) -0.0096(7) 0.0019(7) -0.0069(8)
N3 0.0240(10) 0.0246(10) 0.0164(9) -0.0092(8) 0.0061(8) -0.0147(8)
N4 0.0267(11) 0.0228(10) 0.0216(10) -0.0139(8) 0.0086(8) -0.0147(8)
C1 0.0149(10) 0.0179(10) 0.0192(10) -0.0068(9) 0.0015(8) -0.0053(9)
C2 0.0204(11) 0.0129(10) 0.0193(10) -0.0059(8) 0.0026(9) -0.0060(9)
C3 0.0205(12) 0.0220(11) 0.0276(12) -0.0128(10) 0.0034(10) -0.0106(10)
C4 0.0257(12) 0.0268(12) 0.0252(12) -0.0132(10) 0.0071(10) -0.0088(10)
C5 0.0303(13) 0.0250(12) 0.0196(11) -0.0120(10) 0.0001(10) -0.0058(10)
C6 0.0275(13) 0.0253(12) 0.0250(12) -0.0107(10) -0.0021(10) -0.0118(10)
C7 0.0223(12) 0.0225(11) 0.0220(11) -0.0084(9) 0.0048(10) -0.0119(10)
C8 0.0171(11) 0.0211(11) 0.0187(10) -0.0049(9) -0.0006(9) -0.0082(9)
C9 0.0367(14) 0.0245(12) 0.0213(11) -0.0090(10) 0.0008(10) -0.0132(11)
C10 0.0504(16) 0.0282(14) 0.0277(13) -0.0037(11) -0.0021(12) -0.0251(12)
C11 0.0325(14) 0.0382(14) 0.0196(12) 0.0008(11) 0.0042(11) -0.0238(12)
C12 0.0247(13) 0.0344(13) 0.0204(11) -0.0075(10) 0.0055(10) -0.0092(11)
C13 0.0166(11) 0.0197(10) 0.0206(11) -0.0087(9) 0.0025(9) -0.0069(9)
C14 0.0181(11) 0.0175(10) 0.0188(10) -0.0060(9) 0.0013(9) -0.0077(9)
C15 0.0314(13) 0.0263(12) 0.0249(12) -0.0151(10) 0.0108(11) -0.0127(10)
C16 0.0331(13) 0.0232(12) 0.0292(12) -0.0154(10) 0.0054(10) -0.0127(10)
C17 0.0214(11) 0.0188(11) 0.0238(11) -0.0042(9) 0.0017(9) -0.0111(9)
C18 0.0222(12) 0.0244(12) 0.0212(11) -0.0092(9) 0.0061(10) -0.0098(10)
C19 0.0244(12) 0.0221(11) 0.0226(11) -0.0132(10) 0.0038(9) -0.0088(9)
_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
Br1 C17 1.904(2) . ?
S1 C13 1.675(2) . ?
N1 C12 1.337(3) . ?
N1 C8 1.350(3) . ?
N2 C1 1.295(3) . ?
N2 N3 1.360(2) . ?
N3 C13 1.361(3) . ?
N3 H3N 0.75(2) . ?
N4 C13 1.345(3) . ?
N4 C14 1.409(3) . ?
N4 H4N 0.78(2) . ?
C1 C8 1.489(3) . ?
C1 C2 1.495(3) . ?
C2 C7 1.391(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.92(2) . ?
C4 C5 1.383(3) . ?
C4 H4 0.96(3) . ?
C5 C6 1.379(3) . ?
C5 H5 0.92(2) . ?
C6 C7 1.381(3) . ?
C6 H6 0.92(2) . ?
C7 H7 0.93(2) . ?
C8 C9 1.385(3) . ?
C9 C10 1.384(3) . ?
C9 H9 0.89(2) . ?
C10 C11 1.373(4) . ?
C10 H10 0.93(3) . ?
C11 C12 1.376(3) . ?
C11 H11 0.86(3) . ?
C12 H12 0.94(2) . ?
C14 C19 1.388(3) . ?
C14 C15 1.389(3) . ?
C15 C16 1.383(3) . ?
C15 H15 0.88(3) . ?
C16 C17 1.378(3) . ?
C16 H16 0.92(3) . ?
C17 C18 1.373(3) . ?
C18 C19 1.382(3) . ?
C18 H18 0.93(2) . ?
C19 H19 0.94(2) . ?
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
C12 N1 C8 117.62(19) . . ?
C1 N2 N3 120.33(17) . . ?
N2 N3 C13 119.22(18) . . ?
N2 N3 H3N 118.7(18) . . ?
C13 N3 H3N 121.0(18) . . ?
C13 N4 C14 132.51(19) . . ?
C13 N4 H4N 112.6(17) . . ?
C14 N4 H4N 114.6(17) . . ?
N2 C1 C8 126.91(18) . . ?
N2 C1 C2 113.39(17) . . ?
C8 C1 C2 119.66(17) . . ?
C7 C2 C3 118.65(19) . . ?
C7 C2 C1 121.23(18) . . ?
C3 C2 C1 119.98(18) . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 121.3(13) . . ?
C2 C3 H3 118.1(13) . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 120.5(15) . . ?
C5 C4 H4 119.3(15) . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.5(15) . . ?
C4 C5 H5 119.7(15) . . ?
C5 C6 C7 120.3(2) . . ?
C5 C6 H6 120.1(14) . . ?
C7 C6 H6 119.5(14) . . ?
C6 C7 C2 120.6(2) . . ?
C6 C7 H7 121.4(14) . . ?
C2 C7 H7 117.9(14) . . ?
N1 C8 C9 121.80(19) . . ?
N1 C8 C1 117.36(18) . . ?
C9 C8 C1 120.83(19) . . ?
C10 C9 C8 119.2(2) . . ?
C10 C9 H9 120.9(14) . . ?
C8 C9 H9 119.9(14) . . ?
C11 C10 C9 119.1(2) . . ?
C11 C10 H10 123.3(17) . . ?
C9 C10 H10 117.5(17) . . ?
C10 C11 C12 118.4(2) . . ?
C10 C11 H11 121.3(17) . . ?
C12 C11 H11 120.3(17) . . ?
N1 C12 C11 123.7(2) . . ?
N1 C12 H12 114.4(14) . . ?
C11 C12 H12 121.8(14) . . ?
N4 C13 N3 113.32(18) . . ?
N4 C13 S1 128.14(16) . . ?
N3 C13 S1 118.50(15) . . ?
C19 C14 C15 119.17(19) . . ?
C19 C14 N4 115.85(19) . . ?
C15 C14 N4 124.90(19) . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 119.6(17) . . ?
C14 C15 H15 120.6(17) . . ?
C17 C16 C15 120.0(2) . . ?
C17 C16 H16 119.7(15) . . ?
C15 C16 H16 120.2(15) . . ?
C18 C17 C16 120.91(19) . . ?
C18 C17 Br1 119.73(16) . . ?
C16 C17 Br1 119.31(17) . . ?
C17 C18 C19 119.1(2) . . ?
C17 C18 H18 121.4(14) . . ?
C19 C18 H18 119.4(14) . . ?
C18 C19 C14 120.9(2) . . ?
C18 C19 H19 122.5(13) . . ?
C14 C19 H19 116.6(13) . . ?
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
C1 N2 N3 C13 -179.59(19) . . . . ?
N3 N2 C1 C8 -1.6(3) . . . . ?
N3 N2 C1 C2 176.30(17) . . . . ?
N2 C1 C2 C7 -143.4(2) . . . . ?
C8 C1 C2 C7 34.6(3) . . . . ?
N2 C1 C2 C3 32.1(3) . . . . ?
C8 C1 C2 C3 -149.81(19) . . . . ?
C7 C2 C3 C4 0.7(3) . . . . ?
C1 C2 C3 C4 -175.02(19) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 C2 -0.9(3) . . . . ?
C3 C2 C7 C6 0.5(3) . . . . ?
C1 C2 C7 C6 176.16(19) . . . . ?
C12 N1 C8 C9 -4.1(3) . . . . ?
C12 N1 C8 C1 176.88(18) . . . . ?
N2 C1 C8 N1 25.0(3) . . . . ?
C2 C1 C8 N1 -152.72(19) . . . . ?
N2 C1 C8 C9 -154.0(2) . . . . ?
C2 C1 C8 C9 28.3(3) . . . . ?
N1 C8 C9 C10 4.2(3) . . . . ?
C1 C8 C9 C10 -176.9(2) . . . . ?
C8 C9 C10 C11 -1.0(4) . . . . ?
C9 C10 C11 C12 -2.0(4) . . . . ?
C8 N1 C12 C11 1.0(3) . . . . ?
C10 C11 C12 N1 2.1(4) . . . . ?
C14 N4 C13 N3 175.3(2) . . . . ?
C14 N4 C13 S1 -7.0(4) . . . . ?
N2 N3 C13 N4 -6.0(3) . . . . ?
N2 N3 C13 S1 176.00(15) . . . . ?
C13 N4 C14 C19 164.9(2) . . . . ?
C13 N4 C14 C15 -18.6(4) . . . . ?
C19 C14 C15 C16 1.4(3) . . . . ?
N4 C14 C15 C16 -175.0(2) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C15 C16 C17 C18 -2.1(4) . . . . ?
C15 C16 C17 Br1 175.32(18) . . . . ?
C16 C17 C18 C19 1.3(3) . . . . ?
Br1 C17 C18 C19 -176.12(16) . . . . ?
C17 C18 C19 C14 0.9(3) . . . . ?
C15 C14 C19 C18 -2.3(3) . . . . ?
N4 C14 C19 C18 174.5(2) . . . . ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.273
_refine_diff_density_min -0.302
_refine_diff_density_rms 0.057
_database_code_depnum_ccdc_archive 'CCDC 895056'
#######################################################################
#
# 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_adeline2_p1bar
#TrackingRef 'Adeline2_Deposition_13Oct10.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C20 H18 N4 S'
_chemical_formula_weight 346.44
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_H-M P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 9.5261(12)
_cell_length_b 9.7850(11)
_cell_length_c 11.566(2)
_cell_angle_alpha 101.101(6)
_cell_angle_beta 106.020(6)
_cell_angle_gamma 115.357(4)
_cell_volume 874.4(2)
_cell_formula_units_Z 2
_cell_measurement_temperature 150(2)
_cell_measurement_reflns_used 2720
_cell_measurement_theta_min 2.538
_cell_measurement_theta_max 24.065
_exptl_crystal_description 'Thin needles'
_exptl_crystal_colour Yellow
_exptl_crystal_size_max 0.43
_exptl_crystal_size_mid 0.11
_exptl_crystal_size_min 0.07
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.316
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 364
_exptl_absorpt_coefficient_mu 0.195
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9206
_exptl_absorpt_correction_T_max 0.9871
_exptl_absorpt_process_details 'SADABS (Bruker, 2001)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 150(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Kappa APEXII CCD Diffractometer'
_diffrn_measurement_method '\f scans and \w scans with \k offsets'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 11680
_diffrn_reflns_av_R_equivalents 0.0517
_diffrn_reflns_av_sigmaI/netI 0.0679
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.50
_diffrn_reflns_theta_max 25.00
_reflns_number_total 3070
_reflns_number_gt 2098
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 (Bruker, 2007)'
_computing_cell_refinement 'SAINT (Bruker, 2007)'
_computing_data_reduction 'SAINT '
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL-Plus (Sheldrick, 2008)'
_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^)+(0.0449P)^2^+0.0634P] 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 refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3070
_refine_ls_number_parameters 298
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0808
_refine_ls_R_factor_gt 0.0419
_refine_ls_wR_factor_ref 0.0960
_refine_ls_wR_factor_gt 0.0832
_refine_ls_goodness_of_fit_ref 1.026
_refine_ls_restrained_S_all 1.026
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.01484(7) 0.83257(7) 0.28492(6) 0.0278(2) Uani 1 1 d . . .
N1 N 1.2192(2) 0.6547(2) 0.57918(17) 0.0261(5) Uani 1 1 d . . .
N2 N 0.9624(2) 0.7378(2) 0.58576(16) 0.0229(4) Uani 1 1 d . . .
N3 N 1.0175(2) 0.7624(2) 0.49131(17) 0.0231(4) Uani 1 1 d . . .
H3N H 1.091(3) 0.743(2) 0.4839(19) 0.011(6) Uiso 1 1 d . . .
N4 N 0.8132(2) 0.8218(2) 0.41405(18) 0.0222(4) Uani 1 1 d . . .
H4N H 0.807(2) 0.813(2) 0.487(2) 0.018(6) Uiso 1 1 d . . .
C1 C 1.0321(3) 0.6915(2) 0.6712(2) 0.0220(5) Uani 1 1 d . . .
C2 C 1.1734(3) 0.6606(2) 0.6795(2) 0.0240(5) Uani 1 1 d . . .
C4 C 1.3447(3) 0.6249(3) 0.5850(3) 0.0316(6) Uani 1 1 d . . .
H4 H 1.369(3) 0.617(2) 0.509(2) 0.028(6) Uiso 1 1 d . . .
C5 C 1.4302(3) 0.5993(3) 0.6878(3) 0.0369(6) Uani 1 1 d . . .
H5 H 1.518(3) 0.576(3) 0.689(2) 0.051(8) Uiso 1 1 d . . .
C6 C 1.3857(3) 0.6070(3) 0.7912(3) 0.0378(7) Uani 1 1 d . . .
H6 H 1.446(3) 0.592(3) 0.866(2) 0.055(8) Uiso 1 1 d . . .
C7 C 1.2572(3) 0.6390(3) 0.7879(2) 0.0324(6) Uani 1 1 d . . .
H7 H 1.226(3) 0.643(3) 0.857(2) 0.036(7) Uiso 1 1 d . . .
C8 C 0.9552(3) 0.6699(2) 0.7668(2) 0.0217(5) Uani 1 1 d . . .
C9 C 0.9012(3) 0.5291(3) 0.7957(2) 0.0293(6) Uani 1 1 d . . .
H9 H 0.911(3) 0.444(3) 0.754(2) 0.031(6) Uiso 1 1 d . . .
C10 C 0.8264(3) 0.5103(3) 0.8825(2) 0.0316(6) Uani 1 1 d . . .
H10 H 0.788(3) 0.412(3) 0.900(2) 0.038(6) Uiso 1 1 d . . .
C11 C 0.8052(3) 0.6317(3) 0.9433(2) 0.0296(6) Uani 1 1 d . . .
H11 H 0.754(2) 0.618(2) 1.004(2) 0.024(6) Uiso 1 1 d . . .
C12 C 0.8581(3) 0.7724(3) 0.9153(2) 0.0273(5) Uani 1 1 d . . .
H12 H 0.843(3) 0.863(3) 0.957(2) 0.035(6) Uiso 1 1 d . . .
C13 C 0.9310(3) 0.7911(3) 0.8275(2) 0.0247(5) Uani 1 1 d . . .
H13 H 0.968(2) 0.888(2) 0.8087(18) 0.023(5) Uiso 1 1 d . . .
C14 C 0.9409(3) 0.8058(2) 0.3984(2) 0.0208(5) Uani 1 1 d . . .
C15 C 0.6953(3) 0.8543(2) 0.3383(2) 0.0207(5) Uani 1 1 d . . .
C16 C 0.5874(3) 0.8738(3) 0.3909(2) 0.0251(5) Uani 1 1 d . . .
H16 H 0.600(3) 0.864(2) 0.475(2) 0.034(6) Uiso 1 1 d . . .
C17 C 0.4654(3) 0.9038(3) 0.3250(2) 0.0270(6) Uani 1 1 d . . .
H17 H 0.395(3) 0.916(2) 0.3640(19) 0.028(6) Uiso 1 1 d . . .
C18 C 0.4463(3) 0.9153(2) 0.2045(2) 0.0241(5) Uani 1 1 d . . .
C19 C 0.5550(3) 0.8957(3) 0.1539(2) 0.0282(6) Uani 1 1 d . . .
H19 H 0.541(3) 0.903(2) 0.070(2) 0.024(6) Uiso 1 1 d . . .
C20 C 0.6780(3) 0.8653(3) 0.2182(2) 0.0269(6) Uani 1 1 d . . .
H20 H 0.749(3) 0.852(2) 0.179(2) 0.026(6) Uiso 1 1 d . . .
C21 C 0.3115(4) 0.9443(4) 0.1316(3) 0.0358(6) Uani 1 1 d . . .
H211 H 0.330(4) 0.981(3) 0.064(3) 0.070(9) Uiso 1 1 d . . .
H212 H 0.301(4) 1.022(4) 0.185(3) 0.075(10) Uiso 1 1 d . . .
H213 H 0.202(4) 0.849(4) 0.094(3) 0.078(10) 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
S1 0.0318(4) 0.0362(4) 0.0275(4) 0.0158(3) 0.0171(3) 0.0222(3)
N1 0.0226(11) 0.0244(10) 0.0283(12) 0.0062(9) 0.0081(9) 0.0121(9)
N2 0.0266(11) 0.0214(10) 0.0195(10) 0.0073(8) 0.0100(9) 0.0109(8)
N3 0.0238(11) 0.0290(11) 0.0246(12) 0.0108(9) 0.0118(10) 0.0182(9)
N4 0.0261(11) 0.0307(10) 0.0165(11) 0.0121(9) 0.0108(9) 0.0172(9)
C1 0.0228(12) 0.0155(11) 0.0202(13) 0.0039(10) 0.0027(11) 0.0081(10)
C2 0.0239(13) 0.0169(11) 0.0248(14) 0.0062(10) 0.0058(11) 0.0082(10)
C4 0.0284(15) 0.0285(13) 0.0325(16) 0.0063(12) 0.0093(13) 0.0138(11)
C5 0.0252(15) 0.0332(14) 0.0473(18) 0.0095(13) 0.0082(14) 0.0168(12)
C6 0.0304(15) 0.0404(15) 0.0398(18) 0.0162(13) 0.0046(14) 0.0208(13)
C7 0.0323(15) 0.0348(14) 0.0284(15) 0.0118(12) 0.0082(13) 0.0178(12)
C8 0.0187(12) 0.0231(12) 0.0176(12) 0.0062(10) 0.0033(10) 0.0089(10)
C9 0.0370(15) 0.0230(12) 0.0274(14) 0.0080(11) 0.0116(12) 0.0162(11)
C10 0.0381(15) 0.0259(13) 0.0277(14) 0.0135(12) 0.0134(12) 0.0120(12)
C11 0.0266(14) 0.0365(14) 0.0207(13) 0.0098(12) 0.0084(12) 0.0129(11)
C12 0.0261(14) 0.0301(13) 0.0250(14) 0.0085(11) 0.0064(11) 0.0167(11)
C13 0.0247(13) 0.0228(12) 0.0244(13) 0.0101(11) 0.0057(11) 0.0122(11)
C14 0.0211(12) 0.0167(11) 0.0189(12) 0.0025(10) 0.0047(10) 0.0089(10)
C15 0.0189(12) 0.0183(11) 0.0207(13) 0.0053(10) 0.0048(11) 0.0087(10)
C16 0.0274(14) 0.0300(13) 0.0189(13) 0.0088(11) 0.0097(11) 0.0153(11)
C17 0.0240(14) 0.0299(13) 0.0278(14) 0.0064(11) 0.0118(12) 0.0151(11)
C18 0.0196(13) 0.0215(11) 0.0286(14) 0.0102(10) 0.0078(11) 0.0089(10)
C19 0.0281(14) 0.0354(13) 0.0242(14) 0.0181(11) 0.0110(12) 0.0154(11)
C20 0.0289(14) 0.0370(14) 0.0250(14) 0.0153(11) 0.0158(12) 0.0202(12)
C21 0.0310(17) 0.0428(17) 0.0416(18) 0.0222(15) 0.0137(14) 0.0231(15)
_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 C14 1.665(2) . ?
N1 C4 1.335(3) . ?
N1 C2 1.347(3) . ?
N2 C1 1.301(3) . ?
N2 N3 1.355(2) . ?
N3 C14 1.370(3) . ?
N3 H3N 0.82(2) . ?
N4 C14 1.345(3) . ?
N4 C15 1.414(3) . ?
N4 H4N 0.89(2) . ?
C1 C2 1.484(3) . ?
C1 C8 1.485(3) . ?
C2 C7 1.396(3) . ?
C4 C5 1.377(3) . ?
C4 H4 0.96(2) . ?
C5 C6 1.374(4) . ?
C5 H5 0.95(3) . ?
C6 C7 1.380(3) . ?
C6 H6 0.97(3) . ?
C7 H7 0.93(2) . ?
C8 C9 1.393(3) . ?
C8 C13 1.398(3) . ?
C9 C10 1.379(3) . ?
C9 H9 0.94(2) . ?
C10 C11 1.382(3) . ?
C10 H10 0.95(2) . ?
C11 C12 1.386(3) . ?
C11 H11 0.96(2) . ?
C12 C13 1.378(3) . ?
C12 H12 1.01(2) . ?
C13 H13 0.95(2) . ?
C15 C20 1.384(3) . ?
C15 C16 1.390(3) . ?
C16 C17 1.381(3) . ?
C16 H16 0.97(2) . ?
C17 C18 1.388(3) . ?
C17 H17 0.94(2) . ?
C18 C19 1.383(3) . ?
C18 C21 1.499(3) . ?
C19 C20 1.385(3) . ?
C19 H19 0.96(2) . ?
C20 H20 0.95(2) . ?
C21 H211 0.95(3) . ?
C21 H212 0.95(3) . ?
C21 H213 0.95(3) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C2 118.4(2) . . ?
C1 N2 N3 120.35(18) . . ?
N2 N3 C14 120.70(19) . . ?
N2 N3 H3N 120.9(14) . . ?
C14 N3 H3N 118.1(14) . . ?
C14 N4 C15 132.09(19) . . ?
C14 N4 H4N 111.6(13) . . ?
C15 N4 H4N 116.2(13) . . ?
N2 C1 C2 126.7(2) . . ?
N2 C1 C8 112.94(18) . . ?
C2 C1 C8 120.31(18) . . ?
N1 C2 C7 120.9(2) . . ?
N1 C2 C1 117.93(19) . . ?
C7 C2 C1 121.2(2) . . ?
N1 C4 C5 123.7(2) . . ?
N1 C4 H4 115.1(12) . . ?
C5 C4 H4 121.2(13) . . ?
C6 C5 C4 118.3(3) . . ?
C6 C5 H5 119.9(15) . . ?
C4 C5 H5 121.8(15) . . ?
C5 C6 C7 119.1(2) . . ?
C5 C6 H6 119.6(15) . . ?
C7 C6 H6 121.3(15) . . ?
C6 C7 C2 119.6(2) . . ?
C6 C7 H7 119.2(14) . . ?
C2 C7 H7 121.1(14) . . ?
C9 C8 C13 118.3(2) . . ?
C9 C8 C1 121.8(2) . . ?
C13 C8 C1 119.88(18) . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 118.5(13) . . ?
C8 C9 H9 120.7(13) . . ?
C9 C10 C11 120.5(2) . . ?
C9 C10 H10 119.4(13) . . ?
C11 C10 H10 120.1(13) . . ?
C10 C11 C12 119.4(2) . . ?
C10 C11 H11 120.1(12) . . ?
C12 C11 H11 120.5(12) . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 118.1(12) . . ?
C11 C12 H12 121.5(12) . . ?
C12 C13 C8 120.7(2) . . ?
C12 C13 H13 120.1(12) . . ?
C8 C13 H13 119.2(12) . . ?
N4 C14 N3 113.08(19) . . ?
N4 C14 S1 129.01(16) . . ?
N3 C14 S1 117.91(17) . . ?
C20 C15 C16 118.6(2) . . ?
C20 C15 N4 125.7(2) . . ?
C16 C15 N4 115.60(19) . . ?
C17 C16 C15 120.8(2) . . ?
C17 C16 H16 121.7(13) . . ?
C15 C16 H16 117.5(13) . . ?
C16 C17 C18 121.3(2) . . ?
C16 C17 H17 118.0(12) . . ?
C18 C17 H17 120.7(12) . . ?
C19 C18 C17 117.0(2) . . ?
C19 C18 C21 121.6(2) . . ?
C17 C18 C21 121.3(2) . . ?
C18 C19 C20 122.6(2) . . ?
C18 C19 H19 117.0(12) . . ?
C20 C19 H19 120.4(12) . . ?
C15 C20 C19 119.6(2) . . ?
C15 C20 H20 121.2(13) . . ?
C19 C20 H20 119.2(13) . . ?
C18 C21 H211 114.1(17) . . ?
C18 C21 H212 112.7(18) . . ?
H211 C21 H212 106(2) . . ?
C18 C21 H213 111.6(17) . . ?
H211 C21 H213 106(2) . . ?
H212 C21 H213 105(2) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 N3 C14 177.75(18) . . . . ?
N3 N2 C1 C2 0.2(3) . . . . ?
N3 N2 C1 C8 -179.73(17) . . . . ?
C4 N1 C2 C7 1.2(3) . . . . ?
C4 N1 C2 C1 -179.15(18) . . . . ?
N2 C1 C2 N1 -11.0(3) . . . . ?
C8 C1 C2 N1 168.87(18) . . . . ?
N2 C1 C2 C7 168.6(2) . . . . ?
C8 C1 C2 C7 -11.5(3) . . . . ?
C2 N1 C4 C5 0.1(3) . . . . ?
N1 C4 C5 C6 -0.9(4) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C5 C6 C7 C2 0.9(4) . . . . ?
N1 C2 C7 C6 -1.7(3) . . . . ?
C1 C2 C7 C6 178.6(2) . . . . ?
N2 C1 C8 C9 129.6(2) . . . . ?
C2 C1 C8 C9 -50.3(3) . . . . ?
N2 C1 C8 C13 -48.5(3) . . . . ?
C2 C1 C8 C13 131.6(2) . . . . ?
C13 C8 C9 C10 -0.3(3) . . . . ?
C1 C8 C9 C10 -178.4(2) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C8 -1.0(3) . . . . ?
C9 C8 C13 C12 1.1(3) . . . . ?
C1 C8 C13 C12 179.3(2) . . . . ?
C15 N4 C14 N3 -175.55(19) . . . . ?
C15 N4 C14 S1 4.9(3) . . . . ?
N2 N3 C14 N4 0.8(3) . . . . ?
N2 N3 C14 S1 -179.57(14) . . . . ?
C14 N4 C15 C20 5.5(4) . . . . ?
C14 N4 C15 C16 -175.5(2) . . . . ?
C20 C15 C16 C17 -0.1(3) . . . . ?
N4 C15 C16 C17 -179.12(19) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C16 C17 C18 C21 178.7(2) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C21 C18 C19 C20 -178.6(2) . . . . ?
C16 C15 C20 C19 0.2(3) . . . . ?
N4 C15 C20 C19 179.1(2) . . . . ?
C18 C19 C20 C15 -0.3(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max 0.189
_refine_diff_density_min -0.237
_refine_diff_density_rms 0.050
_database_code_depnum_ccdc_archive 'CCDC 895057'