 
data_01cce003
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C22 H28 N4 O2' 
_chemical_formula_weight          380.48 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P2(1)/c 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    12.6651(5) 
_cell_length_b                    13.6078(7) 
_cell_length_c                    12.3362(5) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  95.807(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      2115.16(16) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used    9423 
_cell_measurement_theta_min       2.91 
_cell_measurement_theta_max       27.48 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             yellow 
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.20 
_exptl_crystal_size_min           0.10 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.195 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              816 
_exptl_absorpt_coefficient_mu     0.078 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9845 
_exptl_absorpt_correction_T_max   0.9922 
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       150(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD' 
_diffrn_measurement_method        'Φ & ω scans' 
_diffrn_detector_area_resol_mean  9.091 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             13194 
_diffrn_reflns_av_R_equivalents   0.0684 
_diffrn_reflns_av_sigmaI/netI     0.0496 
_diffrn_reflns_limit_h_min        -14 
_diffrn_reflns_limit_h_max        14 
_diffrn_reflns_limit_k_min        -15 
_diffrn_reflns_limit_k_max        15 
_diffrn_reflns_limit_l_min        -13 
_diffrn_reflns_limit_l_max        13 
_diffrn_reflns_theta_min          2.99 
_diffrn_reflns_theta_max          23.26 
_reflns_number_total              3030 
_reflns_number_gt                 2264 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'COLLECT (Hooft, 1998)' 
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' 
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_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)+(0.0828P)²+0.0000P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    difmap 
_refine_ls_hydrogen_treatment     refall 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.014(2) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          3030 
_refine_ls_number_parameters      366 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0644 
_refine_ls_R_factor_gt            0.0443 
_refine_ls_wR_factor_ref          0.1216 
_refine_ls_wR_factor_gt           0.1081 
_refine_ls_goodness_of_fit_ref    0.968 
_refine_ls_restrained_S_all       0.968 
_refine_ls_shift/su_max           0.032 
_refine_ls_shift/su_mean          0.004 
 
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 
H7 H 0.6655(15) 0.2027(14) 0.3462(14) 0.026(5) Uiso 1 1 d . . . 
H8 H 0.7614(18) 0.1755(15) 0.1948(16) 0.039(6) Uiso 1 1 d . . . 
H11 H 0.5142(16) 0.0791(15) 0.7642(17) 0.034(5) Uiso 1 1 d . . . 
H12 H 0.6564(18) 0.0433(17) 0.6588(16) 0.045(6) Uiso 1 1 d . . . 
H13 H 0.6393(17) 0.0850(14) 0.4678(15) 0.030(5) Uiso 1 1 d . . . 
H16A H 0.277(2) 0.4273(18) 0.3530(18) 0.053(7) Uiso 1 1 d . . . 
H16B H 0.1573(19) 0.4319(17) 0.3891(16) 0.047(6) Uiso 1 1 d . . . 
H16C H 0.2463(18) 0.3679(16) 0.4614(18) 0.043(6) Uiso 1 1 d . . . 
H17A H 0.204(2) 0.3923(18) 0.1756(17) 0.050(7) Uiso 1 1 d . . . 
H17B H 0.083(2) 0.3729(18) 0.2008(18) 0.060(7) Uiso 1 1 d . . . 
H17C H 0.1409(19) 0.290(2) 0.1421(19) 0.055(7) Uiso 1 1 d . . . 
H18A H 0.1311(16) 0.2332(15) 0.4425(17) 0.039(6) Uiso 1 1 d . . . 
H18B H 0.0464(18) 0.2902(17) 0.3624(15) 0.040(6) Uiso 1 1 d . . . 
H20A H -0.062(2) 0.060(2) 0.3691(19) 0.063(8) Uiso 1 1 d . . . 
H20B H -0.088(3) 0.175(2) 0.378(2) 0.083(10) Uiso 1 1 d . . . 
H20C H -0.006(2) 0.120(2) 0.471(2) 0.078(9) Uiso 1 1 d . . . 
H21A H 0.078(2) 0.155(2) 0.147(2) 0.077(9) Uiso 1 1 d . . . 
H21B H -0.033(2) 0.204(2) 0.1846(18) 0.065(8) Uiso 1 1 d . . . 
H21C H -0.024(2) 0.080(2) 0.1839(19) 0.064(8) Uiso 1 1 d . . . 
H22A H 0.200(2) 0.072(2) 0.289(2) 0.075(9) Uiso 1 1 d . . . 
H22B H 0.174(2) 0.0576(18) 0.417(2) 0.060(7) Uiso 1 1 d . . . 
H22C H 0.109(2) -0.005(2) 0.3230(18) 0.062(7) Uiso 1 1 d . . . 
C1 C 0.8565(2) 0.0997(3) -0.0727(2) 0.0507(7) Uani 1 1 d . . . 
C2 C 0.69062(16) 0.10946(15) -0.00373(16) 0.0316(5) Uani 1 1 d . . . 
C3 C 0.63331(15) 0.13228(15) 0.09229(15) 0.0275(5) Uani 1 1 d . . . 
C4 C 0.52363(16) 0.11740(15) 0.08410(16) 0.0290(5) Uani 1 1 d . . . 
C5 C 0.46836(16) 0.13115(15) 0.17346(15) 0.0282(5) Uani 1 1 d . . . 
C6 C 0.52003(15) 0.16090(14) 0.27386(15) 0.0271(5) Uani 1 1 d . . . 
C7 C 0.62979(16) 0.17804(16) 0.27991(16) 0.0314(5) Uani 1 1 d . . . 
C8 C 0.68534(17) 0.16333(16) 0.19076(16) 0.0325(5) Uani 1 1 d . . . 
C9 C 0.35653(15) 0.20655(15) 0.37641(14) 0.0259(5) Uani 1 1 d . . . 
C10 C 0.41190(15) 0.15824(15) 0.53711(14) 0.0274(5) Uani 1 1 d . . . 
C11 C 0.50952(18) 0.09599(16) 0.68606(17) 0.0351(5) Uani 1 1 d . . . 
C12 C 0.59401(18) 0.07507(17) 0.62510(17) 0.0370(6) Uani 1 1 d . . . 
C13 C 0.58603(17) 0.09734(16) 0.51779(17) 0.0334(5) Uani 1 1 d . . . 
C14 C 0.45954(15) 0.17245(15) 0.36744(15) 0.0269(5) Uani 1 1 d . . . 
C15 C 0.19312(15) 0.30160(16) 0.31031(15) 0.0317(5) Uani 1 1 d . . . 
C16 C 0.2239(2) 0.38929(19) 0.3843(2) 0.0432(6) Uani 1 1 d . . . 
C17 C 0.1529(2) 0.3421(2) 0.1975(2) 0.0450(6) Uani 1 1 d . . . 
C18 C 0.10714(17) 0.24320(16) 0.36266(16) 0.0314(5) Uani 1 1 d . . . 
C19 C 0.06091(16) 0.14366(17) 0.32124(16) 0.0378(6) Uani 1 1 d . . . 
C20 C -0.0306(2) 0.1215(2) 0.3903(3) 0.0568(7) Uani 1 1 d . . . 
C21 C 0.0164(3) 0.1444(3) 0.2014(2) 0.0599(8) Uani 1 1 d . . . 
C22 C 0.1419(2) 0.0605(2) 0.3389(3) 0.0540(7) Uani 1 1 d . . . 
N1 N 0.32800(12) 0.19788(12) 0.47955(11) 0.0282(4) Uani 1 1 d . . . 
N2 N 0.41934(13) 0.13575(13) 0.64335(12) 0.0314(4) Uani 1 1 d . . . 
N3 N 0.49539(12) 0.14216(12) 0.47262(12) 0.0267(4) Uani 1 1 d . . . 
N4 N 0.28772(13) 0.24208(13) 0.29249(13) 0.0309(5) Uani 1 1 d . . . 
O1 O 0.65096(11) 0.07486(12) -0.08759(11) 0.0444(5) Uani 1 1 d . . . 
O2 O 0.79491(11) 0.12962(12) 0.01359(11) 0.0424(4) Uani 1 1 d . . . 
H1A H 0.928(2) 0.1142(18) -0.0460(18) 0.057(7) Uiso 1 1 d . . . 
H1B H 0.831(2) 0.1347(18) -0.141(2) 0.059(8) Uiso 1 1 d . . . 
H1C H 0.844(2) 0.029(2) -0.089(2) 0.081(10) Uiso 1 1 d . . . 
H4 H 0.4895(15) 0.0962(13) 0.0146(15) 0.021(5) Uiso 1 1 d . . . 
H4N H 0.3217(18) 0.2660(15) 0.2388(17) 0.040(6) Uiso 1 1 d . . . 
H5 H 0.3918(19) 0.1155(15) 0.1686(15) 0.043(6) Uiso 1 1 d . . . 
 
 
_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 
C1 O2 1.441(3) . ? 
C2 O1 1.200(2) . ? 
C2 O2 1.345(2) . ? 
C2 C3 1.483(3) . ? 
C3 C8 1.388(3) . ? 
C3 C4 1.397(3) . ? 
C4 C5 1.377(3) . ? 
C5 C6 1.401(3) . ? 
C6 C7 1.404(3) . ? 
C6 C14 1.457(3) . ? 
C7 C8 1.379(3) . ? 
C9 N1 1.363(2) . ? 
C9 N4 1.372(2) . ? 
C9 C14 1.400(3) . ? 
C10 N1 1.331(2) . ? 
C10 N2 1.340(2) . ? 
C10 N3 1.403(2) . ? 
C11 N2 1.324(3) . ? 
C11 C12 1.398(3) . ? 
C12 C13 1.352(3) . ? 
C13 N3 1.368(3) . ? 
C14 N3 1.393(2) . ? 
C15 N4 1.481(3) . ? 
C15 C16 1.529(3) . ? 
C15 C17 1.535(3) . ? 
C15 C18 1.542(3) . ? 
C18 C19 1.542(3) . ? 
C19 C21 1.528(3) . ? 
C19 C22 1.528(4) . ? 
C19 C20 1.536(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 
O1 C2 O2 122.40(18) . . ? 
O1 C2 C3 125.09(19) . . ? 
O2 C2 C3 112.49(17) . . ? 
C8 C3 C4 119.20(18) . . ? 
C8 C3 C2 122.36(18) . . ? 
C4 C3 C2 118.37(17) . . ? 
C5 C4 C3 120.31(19) . . ? 
C4 C5 C6 121.14(19) . . ? 
C5 C6 C7 117.81(18) . . ? 
C5 C6 C14 119.71(17) . . ? 
C7 C6 C14 122.48(17) . . ? 
C8 C7 C6 121.06(19) . . ? 
C7 C8 C3 120.45(19) . . ? 
N1 C9 N4 121.79(16) . . ? 
N1 C9 C14 112.49(16) . . ? 
N4 C9 C14 125.68(16) . . ? 
N1 C10 N2 126.00(18) . . ? 
N1 C10 N3 111.55(15) . . ? 
N2 C10 N3 122.45(17) . . ? 
N2 C11 C12 123.07(19) . . ? 
C13 C12 C11 119.7(2) . . ? 
C12 C13 N3 118.4(2) . . ? 
N3 C14 C9 104.07(15) . . ? 
N3 C14 C6 123.92(17) . . ? 
C9 C14 C6 131.86(17) . . ? 
N4 C15 C16 110.75(17) . . ? 
N4 C15 C17 105.12(16) . . ? 
C16 C15 C17 107.6(2) . . ? 
N4 C15 C18 113.36(17) . . ? 
C16 C15 C18 107.49(17) . . ? 
C17 C15 C18 112.41(18) . . ? 
C15 C18 C19 125.08(17) . . ? 
C21 C19 C22 108.7(2) . . ? 
C21 C19 C20 108.2(2) . . ? 
C22 C19 C20 108.0(2) . . ? 
C21 C19 C18 113.9(2) . . ? 
C22 C19 C18 112.10(19) . . ? 
C20 C19 C18 105.72(19) . . ? 
C10 N1 C9 105.09(15) . . ? 
C11 N2 C10 117.06(18) . . ? 
C13 N3 C14 133.83(17) . . ? 
C13 N3 C10 119.21(16) . . ? 
C14 N3 C10 106.78(15) . . ? 
C9 N4 C15 122.85(15) . . ? 
C2 O2 C1 114.94(18) . . ? 
 
_diffrn_measured_fraction_theta_max    0.997 
_diffrn_reflns_theta_full              23.26 
_diffrn_measured_fraction_theta_full   0.997 
_refine_diff_density_max    0.179 
_refine_diff_density_min   -0.232 
_refine_diff_density_rms    0.045 
