# Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications
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# CCDC
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# This CIF contains data from an original supplementary publication
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# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
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data_dg2j
_database_code_depnum_ccdc_archive 'CCDC 899872'
#TrackingRef '13697_web_deposit_cif_file_0_Sopkova-deOliveiraSantosJana_1346702655.DG2J_CIF.txt'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
'6,7-dimethoxy-1-methyl-1,4-dihydroindeno[1,2-c]
pyrazol-4-amine dihydrochloride'
;
_chemical_name_common ?
_chemical_melting_point 533
_chemical_formula_moiety 'C13 H17 N3 O2, 2(Cl), 2(H2 O)'
_chemical_formula_sum 'C13 H21 Cl2 N3 O4'
_chemical_formula_weight 354.23
_chemical_compound_source synthetised
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_H-M P-1
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 7.2598(2)
_cell_length_b 10.0853(3)
_cell_length_c 12.2011(3)
_cell_angle_alpha 101.0100(10)
_cell_angle_beta 93.643(2)
_cell_angle_gamma 100.4820(10)
_cell_volume 857.77(4)
_cell_formula_units_Z 2
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 9621
_cell_measurement_theta_min 2.42
_cell_measurement_theta_max 38.40
_exptl_crystal_description plate
_exptl_crystal_colour 'translucent colourless'
_exptl_crystal_size_max 0.400
_exptl_crystal_size_mid 0.380
_exptl_crystal_size_min 0.180
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.371
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 372
_exptl_absorpt_coefficient_mu 0.398
_exptl_absorpt_correction_type None
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_diffrn_reflns_number 29736
_diffrn_reflns_av_R_equivalents 0.0248
_diffrn_reflns_av_sigmaI/netI 0.0259
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_limit_l_max 21
_diffrn_reflns_theta_min 2.97
_diffrn_reflns_theta_max 38.62
_reflns_number_total 9651
_reflns_number_gt 6606
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 software'
_computing_cell_refinement 'APEX2 software'
_computing_data_reduction 'BRUKER SAINT'
_computing_structure_solution 'BRUKER SHELXTL (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics MERCURY
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.0730P)^2^+0.0680P] 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 9651
_refine_ls_number_parameters 283
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0647
_refine_ls_R_factor_gt 0.0422
_refine_ls_wR_factor_ref 0.1372
_refine_ls_wR_factor_gt 0.1214
_refine_ls_goodness_of_fit_ref 1.016
_refine_ls_restrained_S_all 1.016
_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
Cl1 Cl 0.28505(4) 0.13902(2) 0.06125(2) 0.04262(7) Uani 1 1 d . . .
C6 C 0.23340(11) 0.57392(7) -0.00501(7) 0.02687(13) Uani 1 1 d . . .
C4 C 0.22156(13) 0.79201(8) 0.11701(7) 0.03006(15) Uani 1 1 d . . .
C7 C 0.20699(11) 0.52200(8) -0.12621(7) 0.02779(14) Uani 1 1 d . . .
C1 C 0.27391(12) 0.51554(8) 0.08644(7) 0.02882(14) Uani 1 1 d . . .
C5 C 0.20699(11) 0.71018(8) 0.01036(7) 0.02749(13) Uani 1 1 d . . .
C8 C 0.16574(12) 0.62201(8) -0.18259(7) 0.02997(14) Uani 1 1 d . . .
C3 C 0.26157(13) 0.73567(8) 0.20847(7) 0.03064(15) Uani 1 1 d . . .
C2 C 0.28782(12) 0.59745(8) 0.19306(7) 0.02963(14) Uani 1 1 d . . .
C9 C 0.13985(14) 0.56173(10) -0.29540(8) 0.03646(18) Uani 1 1 d . . .
C10 C 0.35557(17) 0.42100(11) 0.28573(10) 0.0418(2) Uani 1 1 d . . .
C11 C 0.2754(2) 0.94600(11) 0.34040(10) 0.0507(3) Uani 1 1 d . . .
O2 O 0.27803(14) 0.80228(7) 0.31685(6) 0.04523(18) Uani 1 1 d . . .
O1 O 0.33034(13) 0.55850(7) 0.29052(6) 0.04256(17) Uani 1 1 d . . .
N1 N 0.29060(12) 0.87379(8) -0.11729(7) 0.03300(14) Uani 1 1 d . . .
C12 C 0.15716(12) 0.75079(8) -0.09990(7) 0.02893(14) Uani 1 1 d . . .
C13 C 0.24148(16) 0.27243(9) -0.18903(11) 0.0405(2) Uani 1 1 d . . .
N2 N 0.20718(11) 0.40671(7) -0.20162(6) 0.03210(14) Uani 1 1 d . . .
N3 N 0.16584(13) 0.43192(8) -0.30498(7) 0.03762(17) Uani 1 1 d . . .
Cl2 Cl 0.17897(5) 0.90811(4) 0.64464(2) 0.05852(9) Uani 1 1 d . . .
O4 O 0.45175(19) 0.72781(13) 0.51904(9) 0.0673(3) Uani 1 1 d . . .
O3 O 0.1758(2) 0.26329(14) 0.51061(10) 0.0813(4) Uani 1 1 d . . .
H3 H 0.0325(17) 0.7730(12) -0.1011(10) 0.029(3) Uiso 1 1 d . . .
H1 H 0.205(2) 0.8844(15) 0.1254(13) 0.044(3) Uiso 1 1 d . . .
H2 H 0.292(2) 0.4249(15) 0.0763(13) 0.046(4) Uiso 1 1 d . . .
H4 H 0.118(2) 0.5965(16) -0.3595(14) 0.050(4) Uiso 1 1 d . . .
H7 H 0.416(2) 0.8619(16) -0.1095(14) 0.055(4) Uiso 1 1 d . . .
H8 H 0.273(2) 0.9505(16) -0.0682(13) 0.044(3) Uiso 1 1 d . . .
H6 H 0.259(2) 0.8898(16) -0.1881(14) 0.050(4) Uiso 1 1 d . . .
H5 H 0.169(3) 0.3666(19) -0.3623(16) 0.066(5) Uiso 1 1 d . . .
H9 H 0.162(3) 0.965(2) 0.3156(18) 0.080(6) Uiso 1 1 d . . .
H11 H 0.293(3) 0.973(2) 0.4210(18) 0.076(5) Uiso 1 1 d . . .
H10 H 0.372(3) 1.000(2) 0.3032(16) 0.070(5) Uiso 1 1 d . . .
H13 H 0.449(2) 0.3926(18) 0.2271(16) 0.066(5) Uiso 1 1 d . . .
H12 H 0.239(2) 0.3480(16) 0.2517(14) 0.052(4) Uiso 1 1 d . . .
H14 H 0.396(2) 0.4191(17) 0.3576(15) 0.055(4) Uiso 1 1 d . . .
H16 H 0.404(5) 0.719(3) 0.461(3) 0.137(12) Uiso 1 1 d . . .
H15 H 0.080(4) 0.207(3) 0.473(2) 0.100(7) Uiso 1 1 d . . .
H17 H 0.382(3) 0.789(3) 0.562(2) 0.095(7) Uiso 1 1 d . . .
H18 H 0.256(4) 0.268(3) -0.120(3) 0.117(9) Uiso 1 1 d . . .
H20 H 0.331(3) 0.242(2) -0.239(2) 0.097(7) Uiso 1 1 d . . .
H19 H 0.131(4) 0.201(3) -0.228(2) 0.107(8) Uiso 1 1 d . . .
H21 H 0.278(3) 0.250(2) 0.4903(19) 0.083(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
Cl1 0.04513(13) 0.02970(10) 0.05175(14) -0.00092(8) 0.00165(10) 0.01505(8)
C6 0.0275(3) 0.0236(3) 0.0279(3) -0.0002(2) 0.0028(2) 0.0065(2)
C4 0.0363(4) 0.0238(3) 0.0297(3) 0.0003(2) 0.0044(3) 0.0104(3)
C7 0.0278(3) 0.0240(3) 0.0286(3) -0.0019(2) 0.0023(3) 0.0054(2)
C1 0.0320(4) 0.0227(3) 0.0302(3) 0.0010(2) 0.0019(3) 0.0064(2)
C5 0.0293(3) 0.0255(3) 0.0274(3) 0.0013(2) 0.0034(3) 0.0088(2)
C8 0.0320(4) 0.0280(3) 0.0278(3) -0.0001(2) 0.0008(3) 0.0074(3)
C3 0.0368(4) 0.0256(3) 0.0277(3) -0.0008(2) 0.0029(3) 0.0083(3)
C2 0.0341(4) 0.0252(3) 0.0286(3) 0.0025(2) 0.0010(3) 0.0072(3)
C9 0.0421(5) 0.0356(4) 0.0286(4) -0.0004(3) -0.0007(3) 0.0085(3)
C10 0.0522(6) 0.0342(4) 0.0416(5) 0.0099(3) -0.0011(4) 0.0150(4)
C11 0.0782(9) 0.0321(4) 0.0382(5) -0.0064(4) 0.0024(5) 0.0175(5)
O2 0.0759(5) 0.0306(3) 0.0277(3) -0.0027(2) 0.0021(3) 0.0170(3)
O1 0.0666(5) 0.0319(3) 0.0298(3) 0.0044(2) -0.0022(3) 0.0158(3)
N1 0.0411(4) 0.0266(3) 0.0310(3) 0.0036(2) 0.0009(3) 0.0094(3)
C12 0.0305(4) 0.0275(3) 0.0284(3) 0.0012(2) 0.0011(3) 0.0102(3)
C13 0.0423(5) 0.0256(3) 0.0516(6) 0.0000(3) 0.0079(4) 0.0088(3)
N2 0.0361(4) 0.0254(3) 0.0311(3) -0.0032(2) 0.0030(3) 0.0060(2)
N3 0.0454(4) 0.0335(3) 0.0289(3) -0.0049(3) 0.0017(3) 0.0073(3)
Cl2 0.0708(2) 0.0723(2) 0.03569(13) 0.00606(12) -0.00244(12) 0.03035(16)
O4 0.0854(8) 0.0789(7) 0.0404(5) 0.0001(4) -0.0054(5) 0.0407(6)
O3 0.0758(8) 0.0813(8) 0.0614(7) -0.0379(6) 0.0148(6) 0.0025(6)
_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
C6 C1 1.3966(12) . ?
C6 C5 1.4008(10) . ?
C6 C7 1.4592(11) . ?
C4 C3 1.3833(12) . ?
C4 C5 1.3878(11) . ?
C4 H1 0.948(15) . ?
C7 N2 1.3381(10) . ?
C7 C8 1.3888(12) . ?
C1 C2 1.3883(11) . ?
C1 H2 0.932(15) . ?
C5 C12 1.5202(12) . ?
C8 C9 1.3804(12) . ?
C8 C12 1.4985(11) . ?
C3 O2 1.3512(10) . ?
C3 C2 1.4198(11) . ?
C2 O1 1.3563(11) . ?
C9 N3 1.3406(13) . ?
C9 H4 0.933(16) . ?
C10 O1 1.4223(12) . ?
C10 H13 1.054(19) . ?
C10 H12 1.023(16) . ?
C10 H14 0.912(17) . ?
C11 O2 1.4268(12) . ?
C11 H9 0.92(2) . ?
C11 H11 0.96(2) . ?
C11 H10 0.997(19) . ?
N1 C12 1.4872(12) . ?
N1 H7 0.940(17) . ?
N1 H8 0.917(16) . ?
N1 H6 0.931(16) . ?
C12 H3 0.971(12) . ?
C13 N2 1.4550(12) . ?
C13 H18 0.85(3) . ?
C13 H20 0.97(2) . ?
C13 H19 1.00(3) . ?
N2 N3 1.3591(12) . ?
N3 H5 0.87(2) . ?
O4 H16 0.75(3) . ?
O4 H17 0.97(3) . ?
O3 H15 0.86(3) . ?
O3 H21 0.83(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
C1 C6 C5 121.15(7) . . ?
C1 C6 C7 133.55(7) . . ?
C5 C6 C7 105.30(7) . . ?
C3 C4 C5 118.46(7) . . ?
C3 C4 H1 121.8(9) . . ?
C5 C4 H1 119.7(9) . . ?
N2 C7 C8 108.73(8) . . ?
N2 C7 C6 140.06(8) . . ?
C8 C7 C6 111.19(6) . . ?
C2 C1 C6 117.67(7) . . ?
C2 C1 H2 121.1(9) . . ?
C6 C1 H2 121.2(9) . . ?
C4 C5 C6 121.09(7) . . ?
C4 C5 C12 126.51(7) . . ?
C6 C5 C12 112.38(7) . . ?
C9 C8 C7 106.43(7) . . ?
C9 C8 C12 143.55(8) . . ?
C7 C8 C12 109.93(7) . . ?
O2 C3 C4 125.03(7) . . ?
O2 C3 C2 114.44(8) . . ?
C4 C3 C2 120.53(7) . . ?
O1 C2 C1 125.42(7) . . ?
O1 C2 C3 113.46(7) . . ?
C1 C2 C3 121.11(8) . . ?
N3 C9 C8 107.44(8) . . ?
N3 C9 H4 120.1(10) . . ?
C8 C9 H4 132.3(10) . . ?
O1 C10 H13 112.0(9) . . ?
O1 C10 H12 113.7(9) . . ?
H13 C10 H12 98.9(14) . . ?
O1 C10 H14 104.6(11) . . ?
H13 C10 H14 113.3(15) . . ?
H12 C10 H14 114.6(14) . . ?
O2 C11 H9 112.6(13) . . ?
O2 C11 H11 104.7(12) . . ?
H9 C11 H11 108.4(17) . . ?
O2 C11 H10 112.5(11) . . ?
H9 C11 H10 105.5(16) . . ?
H11 C11 H10 113.2(16) . . ?
C3 O2 C11 118.46(8) . . ?
C2 O1 C10 118.51(7) . . ?
C12 N1 H7 111.3(9) . . ?
C12 N1 H8 109.4(9) . . ?
H7 N1 H8 111.5(13) . . ?
C12 N1 H6 108.7(9) . . ?
H7 N1 H6 111.1(14) . . ?
H8 N1 H6 104.7(13) . . ?
N1 C12 C8 113.05(7) . . ?
N1 C12 C5 112.52(7) . . ?
C8 C12 C5 101.14(6) . . ?
N1 C12 H3 107.3(7) . . ?
C8 C12 H3 112.9(7) . . ?
C5 C12 H3 109.9(7) . . ?
N2 C13 H18 110.8(19) . . ?
N2 C13 H20 111.3(13) . . ?
H18 C13 H20 120(2) . . ?
N2 C13 H19 108.1(15) . . ?
H18 C13 H19 110(2) . . ?
H20 C13 H19 95(2) . . ?
C7 N2 N3 107.53(7) . . ?
C7 N2 C13 131.79(9) . . ?
N3 N2 C13 120.68(8) . . ?
C9 N3 N2 109.86(7) . . ?
C9 N3 H5 133.1(12) . . ?
N2 N3 H5 116.9(12) . . ?
H16 O4 H17 101(3) . . ?
H15 O3 H21 115(2) . . ?
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full 38.62
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max 0.485
_refine_diff_density_min -0.535
_refine_diff_density_rms 0.051
data_dg17j
_database_code_depnum_ccdc_archive 'CCDC 899873'
#TrackingRef '13698_web_deposit_cif_file_1_Sopkova-deOliveiraSantosJana_1346702655.dg17j_cif.txt'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
'N-{(5E)-5-[(dimethylamino)methylene]-6-oxo-5,6-dihydro-
4H-cyclopenta[b]thien-4-yl}-2.2,2-trifluoroacetamide'
;
_chemical_name_common ?
_chemical_melting_point 533
_chemical_formula_moiety 'C12 H11 F3 N2 O2 S'
_chemical_formula_sum 'C12 H11 F3 N2 O2 S'
_chemical_formula_weight 304.29
_chemical_compound_source synthetised
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M P2(1)/c
_symmetry_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 6.7601(2)
_cell_length_b 8.9249(3)
_cell_length_c 22.5441(5)
_cell_angle_alpha 90.00
_cell_angle_beta 97.265(2)
_cell_angle_gamma 90.00
_cell_volume 1349.24(7)
_cell_formula_units_Z 4
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 4081
_cell_measurement_theta_min 2.92
_cell_measurement_theta_max 28.74
_exptl_crystal_description plate
_exptl_crystal_colour 'translucent pale yellow'
_exptl_crystal_size_max 0.510
_exptl_crystal_size_mid 0.420
_exptl_crystal_size_min 0.090
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.498
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 624
_exptl_absorpt_coefficient_mu 0.277
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.6275
_exptl_absorpt_correction_T_max 0.7458
_exptl_absorpt_process_details 'Bruker SAINT'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_diffrn_reflns_number 12448
_diffrn_reflns_av_R_equivalents 0.0264
_diffrn_reflns_av_sigmaI/netI 0.0246
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -30
_diffrn_reflns_limit_l_max 29
_diffrn_reflns_theta_min 2.46
_diffrn_reflns_theta_max 28.28
_reflns_number_total 3317
_reflns_number_gt 2268
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 software'
_computing_cell_refinement 'APEX2 software'
_computing_data_reduction 'BRUKER SAINT'
_computing_structure_solution 'BRUKER SHELXTL (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics MERCURY
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.0519P)^2^+0.3328P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3317
_refine_ls_number_parameters 274
_refine_ls_number_restraints 374
_refine_ls_R_factor_all 0.0743
_refine_ls_R_factor_gt 0.0465
_refine_ls_wR_factor_ref 0.1259
_refine_ls_wR_factor_gt 0.1115
_refine_ls_goodness_of_fit_ref 1.052
_refine_ls_restrained_S_all 1.020
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1483(2) 0.19204(16) 0.61207(5) 0.0476(3) Uani 1 1 d . . .
H1 H 0.0293 0.1588 0.6022 0.057 Uiso 1 1 calc R . .
C1 C 0.2902(2) -0.0024(2) 0.55147(6) 0.0468(4) Uani 1 1 d D . .
O2 O 0.3467(2) 0.32467(19) 0.68184(7) 0.0811(5) Uani 1 1 d . . .
N2 N 0.3656(2) -0.16600(19) 0.63932(7) 0.0616(4) Uani 1 1 d . . .
C7 C 0.3011(2) 0.15874(19) 0.57305(7) 0.0472(4) Uani 1 1 d . B .
H7 H 0.4338 0.1790 0.5944 0.057 Uiso 1 1 calc R A 1
C9 C 0.3125(2) -0.1343(2) 0.58188(8) 0.0521(4) Uani 1 1 d . B .
H9 H 0.2853 -0.2184 0.5579 0.063 Uiso 1 1 calc R . .
C15 C 0.1865(3) 0.2710(2) 0.66168(7) 0.0527(4) Uani 1 1 d . B .
C14 C 0.0100(4) 0.2907(3) 0.69714(8) 0.0672(6) Uani 1 1 d . . .
C11 C 0.3622(4) -0.3209(3) 0.66049(13) 0.0893(8) Uani 1 1 d . B .
H11A H 0.3265 -0.3865 0.6271 0.134 Uiso 1 1 calc R . .
H11B H 0.2661 -0.3302 0.6882 0.134 Uiso 1 1 calc R . .
H11C H 0.4919 -0.3476 0.6801 0.134 Uiso 1 1 calc R . .
C12 C 0.4371(4) -0.0572(3) 0.68394(9) 0.0878(7) Uani 1 1 d . B .
H12A H 0.4866 0.0288 0.6649 0.132 Uiso 1 1 calc R . .
H12B H 0.5426 -0.1004 0.7111 0.132 Uiso 1 1 calc R . .
H12C H 0.3300 -0.0275 0.7056 0.132 Uiso 1 1 calc R . .
C2A C 0.246(4) 0.0053(11) 0.48590(19) 0.048(2) Uani 0.489(14) 1 d PDU B 1
O1A O 0.225(3) -0.1027(14) 0.4517(3) 0.070(2) Uani 0.489(14) 1 d PDU B 1
C6A C 0.269(3) 0.2501(14) 0.5185(5) 0.053(2) Uani 0.489(14) 1 d PDU B 1
C3A C 0.233(3) 0.1637(12) 0.4685(4) 0.053(2) Uani 0.489(14) 1 d PDU B 1
C5A C 0.270(3) 0.4038(13) 0.5052(6) 0.073(3) Uani 0.489(14) 1 d PDU B 1
H5A H 0.3011 0.4787 0.5335 0.088 Uiso 0.489(14) 1 calc PR B 1
C4A C 0.218(3) 0.4294(11) 0.4459(6) 0.084(2) Uani 0.489(14) 1 d PDU B 1
H4A H 0.2049 0.5248 0.4292 0.101 Uiso 0.489(14) 1 calc PR B 1
S1A S 0.1808(14) 0.2687(9) 0.4050(3) 0.0793(13) Uani 0.489(14) 1 d PDU B 1
F4A F -0.1572(11) 0.2635(15) 0.6687(4) 0.105(3) Uani 0.489(14) 1 d PU B 1
F5A F 0.040(2) 0.2160(18) 0.7449(5) 0.154(4) Uani 0.489(14) 1 d PU B 1
F6A F 0.0023(19) 0.4293(9) 0.7142(6) 0.147(4) Uani 0.489(14) 1 d PU B 1
C2B C 0.236(4) -0.0189(11) 0.4873(2) 0.057(3) Uani 0.511(14) 1 d PDU B 2
O1B O 0.214(3) -0.1320(14) 0.4569(3) 0.068(2) Uani 0.511(14) 1 d PDU B 2
C6B C 0.254(3) 0.2396(13) 0.5121(5) 0.058(3) Uani 0.511(14) 1 d PDU B 2
C3B C 0.219(3) 0.1367(13) 0.4677(3) 0.059(2) Uani 0.511(14) 1 d PDU B 2
C5B C 0.233(3) 0.3894(13) 0.4935(6) 0.079(3) Uani 0.511(14) 1 d PDU B 2
H5B H 0.2439 0.4726 0.5185 0.095 Uiso 0.511(14) 1 calc PR B 2
C4B C 0.193(3) 0.3931(13) 0.4328(6) 0.100(3) Uani 0.511(14) 1 d PDU B 2
H4B H 0.1772 0.4822 0.4114 0.120 Uiso 0.511(14) 1 calc PR B 2
S1B S 0.1735(12) 0.2216(12) 0.3993(3) 0.0895(18) Uani 0.511(14) 1 d PDU B 2
F1B F -0.1318(17) 0.1872(14) 0.6854(5) 0.121(3) Uani 0.511(14) 1 d PU B 2
F2B F 0.0568(14) 0.2766(13) 0.7538(2) 0.121(4) Uani 0.511(14) 1 d PU B 2
F3B F -0.0719(18) 0.4196(12) 0.6887(5) 0.152(4) Uani 0.511(14) 1 d PU B 2
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
N1 0.0479(8) 0.0552(9) 0.0388(6) -0.0076(6) 0.0025(5) -0.0041(6)
C1 0.0364(8) 0.0612(11) 0.0424(8) -0.0077(7) 0.0030(6) -0.0008(7)
O2 0.0842(10) 0.0853(11) 0.0696(9) -0.0299(8) -0.0057(8) -0.0195(8)
N2 0.0603(9) 0.0600(10) 0.0643(9) 0.0095(8) 0.0069(7) 0.0068(8)
C7 0.0423(9) 0.0567(11) 0.0417(8) -0.0018(7) 0.0021(6) -0.0009(7)
C9 0.0406(9) 0.0557(11) 0.0605(10) -0.0095(8) 0.0084(7) -0.0007(8)
C15 0.0681(11) 0.0475(10) 0.0408(8) -0.0040(7) 0.0000(8) -0.0017(8)
C14 0.0929(16) 0.0655(14) 0.0445(9) -0.0071(9) 0.0135(10) -0.0004(12)
C11 0.0918(17) 0.0692(15) 0.1106(19) 0.0295(14) 0.0272(15) 0.0062(13)
C12 0.117(2) 0.0845(17) 0.0548(11) 0.0065(11) -0.0186(12) 0.0163(14)
C2A 0.030(4) 0.078(4) 0.035(4) -0.022(3) 0.003(3) -0.008(4)
O1A 0.052(3) 0.097(4) 0.065(4) -0.037(3) 0.015(3) -0.010(4)
C6A 0.041(4) 0.067(4) 0.050(4) -0.008(3) 0.006(3) 0.002(3)
C3A 0.033(3) 0.077(3) 0.049(4) 0.001(3) 0.008(3) 0.000(3)
C5A 0.075(7) 0.070(4) 0.073(5) 0.006(3) 0.008(4) 0.003(3)
C4A 0.075(5) 0.089(4) 0.091(6) 0.029(4) 0.018(5) 0.010(4)
S1A 0.0654(13) 0.123(3) 0.0506(12) 0.0187(14) 0.0109(9) 0.0130(19)
F4A 0.065(2) 0.171(8) 0.083(3) -0.051(4) 0.022(2) -0.004(4)
F5A 0.195(9) 0.174(8) 0.106(6) 0.081(5) 0.070(6) 0.040(6)
F6A 0.192(8) 0.083(5) 0.189(8) -0.078(6) 0.110(6) -0.030(5)
C2B 0.032(5) 0.088(4) 0.050(5) -0.004(3) 0.006(3) 0.004(5)
O1B 0.047(4) 0.101(5) 0.053(3) -0.033(3) -0.005(3) -0.004(4)
C6B 0.049(5) 0.080(5) 0.046(3) 0.025(4) 0.010(3) 0.003(4)
C3B 0.043(5) 0.107(5) 0.027(3) 0.016(3) 0.004(2) 0.004(5)
C5B 0.072(6) 0.092(5) 0.074(5) 0.037(4) 0.009(4) 0.005(4)
C4B 0.105(8) 0.125(7) 0.071(5) 0.047(5) 0.017(5) 0.017(8)
S1B 0.0575(12) 0.167(5) 0.0442(12) 0.038(2) 0.0096(10) 0.018(3)
F1B 0.108(5) 0.149(7) 0.119(6) -0.064(4) 0.061(5) -0.054(5)
F2B 0.123(4) 0.210(10) 0.0302(16) -0.011(4) 0.0064(18) -0.028(5)
F3B 0.201(8) 0.129(7) 0.143(6) 0.057(5) 0.094(5) 0.101(7)
_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 C15 1.320(2) . ?
N1 C7 1.469(2) . ?
N1 H1 0.8600 . ?
C1 C9 1.360(3) . ?
C1 C2B 1.454(4) . ?
C1 C2A 1.472(4) . ?
C1 C7 1.517(2) . ?
O2 C15 1.218(2) . ?
N2 C9 1.330(2) . ?
N2 C12 1.437(3) . ?
N2 C11 1.464(3) . ?
C7 C6A 1.469(13) . ?
C7 C6B 1.550(11) . ?
C7 H7 0.9800 . ?
C9 H9 0.9300 . ?
C15 C14 1.528(3) . ?
C14 F4A 1.251(8) . ?
C14 F5A 1.261(9) . ?
C14 F3B 1.281(7) . ?
C14 F2B 1.283(6) . ?
C14 F6A 1.299(7) . ?
C14 F1B 1.333(9) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C2A O1A 1.232(4) . ?
C2A C3A 1.467(4) . ?
C6A C3A 1.360(4) . ?
C6A C5A 1.404(5) . ?
C3A S1A 1.711(4) . ?
C5A C4A 1.358(5) . ?
C5A H5A 0.9300 . ?
C4A S1A 1.706(4) . ?
C4A H4A 0.9300 . ?
C2B O1B 1.219(4) . ?
C2B C3B 1.457(4) . ?
C6B C3B 1.356(4) . ?
C6B C5B 1.403(5) . ?
C3B S1B 1.712(4) . ?
C5B C4B 1.359(5) . ?
C5B H5B 0.9300 . ?
C4B S1B 1.705(5) . ?
C4B H4B 0.9300 . ?
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
C15 N1 C7 122.58(15) . . ?
C15 N1 H1 118.7 . . ?
C7 N1 H1 118.7 . . ?
C9 C1 C2B 114.3(4) . . ?
C9 C1 C2A 122.8(4) . . ?
C2B C1 C2A 9.0(10) . . ?
C9 C1 C7 131.34(14) . . ?
C2B C1 C7 114.2(4) . . ?
C2A C1 C7 105.8(4) . . ?
C9 N2 C12 124.29(17) . . ?
C9 N2 C11 120.36(19) . . ?
C12 N2 C11 115.30(19) . . ?
N1 C7 C6A 110.5(8) . . ?
N1 C7 C1 112.00(13) . . ?
C6A C7 C1 105.1(5) . . ?
N1 C7 C6B 110.9(7) . . ?
C6A C7 C6B 6.6(10) . . ?
C1 C7 C6B 99.3(4) . . ?
N1 C7 H7 109.7 . . ?
C6A C7 H7 109.7 . . ?
C1 C7 H7 109.7 . . ?
C6B C7 H7 115.0 . . ?
N2 C9 C1 132.38(17) . . ?
N2 C9 H9 113.8 . . ?
C1 C9 H9 113.8 . . ?
O2 C15 N1 126.55(18) . . ?
O2 C15 C14 118.42(16) . . ?
N1 C15 C14 115.00(16) . . ?
F4A C14 F5A 111.9(7) . . ?
F4A C14 F3B 75.7(6) . . ?
F5A C14 F3B 128.5(6) . . ?
F4A C14 F2B 125.8(6) . . ?
F5A C14 F2B 26.5(8) . . ?
F3B C14 F2B 106.5(6) . . ?
F4A C14 F6A 105.6(6) . . ?
F5A C14 F6A 105.0(6) . . ?
F3B C14 F6A 32.4(5) . . ?
F2B C14 F6A 79.2(6) . . ?
F4A C14 F1B 35.3(4) . . ?
F5A C14 F1B 80.7(6) . . ?
F3B C14 F1B 107.8(6) . . ?
F2B C14 F1B 102.2(6) . . ?
F6A C14 F1B 131.6(6) . . ?
F4A C14 C15 115.1(4) . . ?
F5A C14 C15 109.5(6) . . ?
F3B C14 C15 112.1(4) . . ?
F2B C14 C15 113.5(5) . . ?
F6A C14 C15 109.1(5) . . ?
F1B C14 C15 114.0(4) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1A C2A C3A 126.1(4) . . ?
O1A C2A C1 125.8(4) . . ?
C3A C2A C1 108.1(4) . . ?
C3A C6A C5A 112.5(10) . . ?
C3A C6A C7 111.8(8) . . ?
C5A C6A C7 135.7(10) . . ?
C6A C3A C2A 109.1(7) . . ?
C6A C3A S1A 112.3(8) . . ?
C2A C3A S1A 138.6(7) . . ?
C4A C5A C6A 111.5(10) . . ?
C4A C5A H5A 124.2 . . ?
C6A C5A H5A 124.2 . . ?
C5A C4A S1A 113.1(8) . . ?
C5A C4A H4A 123.4 . . ?
S1A C4A H4A 123.4 . . ?
C4A S1A C3A 90.4(6) . . ?
O1B C2B C1 129.8(4) . . ?
O1B C2B C3B 128.3(4) . . ?
C1 C2B C3B 101.8(4) . . ?
C3B C6B C5B 115.0(9) . . ?
C3B C6B C7 109.6(7) . . ?
C5B C6B C7 135.3(9) . . ?
C6B C3B C2B 115.0(6) . . ?
C6B C3B S1B 111.1(7) . . ?
C2B C3B S1B 133.9(7) . . ?
C4B C5B C6B 108.9(9) . . ?
C4B C5B H5B 125.6 . . ?
C6B C5B H5B 125.6 . . ?
C5B C4B S1B 114.8(8) . . ?
C5B C4B H4B 122.6 . . ?
S1B C4B H4B 122.6 . . ?
C4B S1B C3B 90.1(6) . . ?
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full 28.28
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max 0.251
_refine_diff_density_min -0.129
_refine_diff_density_rms 0.034