 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C22 H25 N7 O5'
_chemical_formula_weight          467.49
 
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                    15.6546(4)
_cell_length_b                    12.8752(4)
_cell_length_c                    11.5653(6)
_cell_angle_alpha                 90.00
_cell_angle_beta                  97.682(3)
_cell_angle_gamma                 90.00
_cell_volume                      2310.14(15)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        unknown
_exptl_crystal_colour             unknown
_exptl_crystal_size_max           0.5
_exptl_crystal_size_mid           0.2
_exptl_crystal_size_min           0.2
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.344
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              984
_exptl_absorpt_coefficient_mu     0.098
_exptl_absorpt_correction_type    none

 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source         'rotating anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Delft instruments FAST area detector'
_diffrn_measurement_method
 'Intensity measurements as described by Darr, Drake, Hursthouse & Malik (1993)'
_diffrn_standards_number         'None'
_diffrn_standards_interval_count 'N/A'
_diffrn_standards_interval_time  'N/A'
_diffrn_standards_decay_%        'N/A'
_diffrn_reflns_number             34350
_diffrn_reflns_av_R_equivalents   0.0909
_diffrn_reflns_av_sigmaI/netI     0.0476
_diffrn_reflns_limit_h_min        -19
_diffrn_reflns_limit_h_max        19
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          2.06
_diffrn_reflns_theta_max          26.35
_reflns_number_total              4707
_reflns_number_gt                 3127
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        'MADNES (Pflugrath & Messerschmidt, 1989)'
_computing_cell_refinement        REFINE
_computing_data_reduction         'ABSURD (Karaulov, 1992)'
_computing_structure_solution     'SIR92 (Altomare, Cascarano, Giacovazzo & Guaglitardi, 1993)'
_computing_structure_refinement   'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material   SHELXL97
 
_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 > 2σ(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)+(0.0662P)²+1.0214P] 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          4707
_refine_ls_number_parameters      309
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0977
_refine_ls_R_factor_gt            0.0583
_refine_ls_wR_factor_ref          0.1529
_refine_ls_wR_factor_gt           0.1330
_refine_ls_goodness_of_fit_ref    1.025
_refine_ls_restrained_S_all       1.025
_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
O3 O 0.63230(10) 0.79718(11) 0.01308(13) 0.0422(4) Uani 1 1 d . . .
N2 N 0.37519(12) 0.60136(13) 0.02167(16) 0.0378(4) Uani 1 1 d . . .
H2 H 0.3438 0.6084 0.0789 0.045 Uiso 1 1 calc R . .
O2 O 0.42086(10) 0.77019(12) 0.04615(14) 0.0476(4) Uani 1 1 d . . .
N1 N 0.32766(12) 0.42836(14) 0.01231(16) 0.0412(5) Uani 1 1 d . . .
H1 H 0.3357 0.3654 -0.0137 0.049 Uiso 1 1 calc R . .
N5 N 0.51496(12) 0.72268(13) -0.17022(15) 0.0364(4) Uani 1 1 d . . .
N3 N 0.41661(11) 0.48361(13) -0.11773(15) 0.0371(4) Uani 1 1 d . . .
O1 O 0.25869(12) 0.51767(14) 0.14230(17) 0.0619(5) Uani 1 1 d . . .
N4 N 0.50810(13) 0.56288(14) -0.24668(16) 0.0412(5) Uani 1 1 d . . .
C8 C 0.46065(14) 0.56660(16) -0.15496(18) 0.0346(5) Uani 1 1 d . . .
C6 C 0.42120(13) 0.68853(16) -0.00861(18) 0.0352(5) Uani 1 1 d . . .
C7 C 0.46368(14) 0.66411(16) -0.10658(17) 0.0340(5) Uani 1 1 d . . .
N6 N 0.60226(12) 0.96411(13) -0.03747(17) 0.0416(5) Uani 1 1 d . . .
H6 H 0.5702 1.0059 -0.0854 0.050 Uiso 1 1 calc R . .
C5 C 0.37535(13) 0.50666(16) -0.03070(18) 0.0346(5) Uani 1 1 d . . .
C11 C 0.59356(14) 0.86193(16) -0.05277(19) 0.0353(5) Uani 1 1 d . . .
N7 N 0.77259(14) 1.06426(17) -0.06677(19) 0.0532(5) Uani 1 1 d . . .
C9 C 0.53812(15) 0.65843(17) -0.25220(19) 0.0407(5) Uani 1 1 d . . .
H9 H 0.5730 0.6798 -0.3091 0.049 Uiso 1 1 calc R . .
C4 C 0.26944(15) 0.43702(19) 0.0905(2) 0.0462(6) Uani 1 1 d . . .
O5 O 0.77542(14) 1.22009(16) 0.0295(2) 0.0817(7) Uani 1 1 d . . .
C12 C 0.66270(16) 1.00921(18) 0.0555(2) 0.0458(6) Uani 1 1 d . . .
H12A H 0.6568 0.9732 0.1296 0.055 Uiso 1 1 calc R . .
H12B H 0.6479 1.0832 0.0648 0.055 Uiso 1 1 calc R . .
C10 C 0.53331(16) 0.83290(16) -0.16156(19) 0.0417(5) Uani 1 1 d . . .
H10A H 0.4785 0.8712 -0.1620 0.050 Uiso 1 1 calc R . .
H10B H 0.5594 0.8550 -0.2310 0.050 Uiso 1 1 calc R . .
C13 C 0.75550(17) 1.0015(2) 0.0319(2) 0.0541(6) Uani 1 1 d . . .
H13A H 0.7941 1.0241 0.1023 0.065 Uiso 1 1 calc R . .
H13B H 0.7690 0.9280 0.0168 0.065 Uiso 1 1 calc R . .
C17 C 0.78462(17) 1.1713(2) -0.0573(3) 0.0600(7) Uani 1 1 d . . .
C3 C 0.21752(19) 0.3399(2) 0.1024(3) 0.0626(8) Uani 1 1 d . . .
H3 H 0.2546 0.2788 0.0895 0.075 Uiso 1 1 calc R . .
C16 C 0.8150(2) 1.2098(3) -0.1653(3) 0.0813(10) Uani 1 1 d . . .
H16 H 0.7757 1.2645 -0.2040 0.098 Uiso 1 1 calc R . .
C2 C 0.1909(2) 0.3298(3) 0.2221(3) 0.0852(10) Uani 1 1 d . . .
H2A H 0.2422 0.3313 0.2808 0.128 Uiso 1 1 calc R . .
H2B H 0.1604 0.2639 0.2278 0.128 Uiso 1 1 calc R . .
H2C H 0.1527 0.3876 0.2358 0.128 Uiso 1 1 calc R . .
C14 C 0.7910(2) 1.0260(3) -0.1712(3) 0.0765(9) Uani 1 1 d . . .
C15 C 0.8177(2) 1.1152(3) -0.2426(3) 0.0898(12) Uani 1 1 d . . .
H15 H 0.7784 1.1230 -0.3177 0.108 Uiso 1 1 calc R . .
C21 C 0.9663(2) 1.0850(4) -0.1467(4) 0.1023(14) Uani 1 1 d . . .
H21 H 0.9961 1.0220 -0.1263 0.123 Uiso 1 1 calc R . .
C20 C 0.9156(3) 1.1100(5) -0.2631(4) 0.1203(17) Uani 1 1 d . . .
H20 H 0.9286 1.0670 -0.3306 0.144 Uiso 1 1 calc R . .
C18 C 0.9113(2) 1.2475(3) -0.1464(4) 0.1058(14) Uani 1 1 d . . .
H18 H 0.9213 1.3203 -0.1173 0.127 Uiso 1 1 calc R . .
C22 C 0.9623(2) 1.1653(4) -0.0784(4) 0.0978(13) Uani 1 1 d . . .
H22 H 0.9875 1.1702 0.0008 0.117 Uiso 1 1 calc R . .
C19 C 0.9338(3) 1.2252(5) -0.2699(4) 0.150(2) Uani 1 1 d . . .
H19A H 0.8949 1.2608 -0.3320 0.180 Uiso 1 1 calc R . .
H19B H 0.9947 1.2405 -0.2778 0.180 Uiso 1 1 calc R . .
C1 C 0.1418(3) 0.3401(5) 0.0075(4) 0.150(2) Uani 1 1 d . . .
H1A H 0.1009 0.3941 0.0236 0.225 Uiso 1 1 calc R . .
H1B H 0.1132 0.2722 0.0047 0.225 Uiso 1 1 calc R . .
H1C H 0.1618 0.3540 -0.0677 0.225 Uiso 1 1 calc R . .
O4 O 0.7872(2) 0.9348(2) -0.1956(3) 0.1161(10) Uani 1 1 d . . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O3 C11 1.233(2) . ?
N2 C5 1.362(3) . ?
N2 C6 1.403(3) . ?
N2 H2 0.8800 . ?
O2 C6 1.228(2) . ?
N1 C4 1.372(3) . ?
N1 C5 1.386(3) . ?
N1 H1 0.8800 . ?
N5 C9 1.344(3) . ?
N5 C7 1.383(3) . ?
N5 C10 1.449(3) . ?
N3 C5 1.301(3) . ?
N3 C8 1.372(3) . ?
O1 C4 1.221(3) . ?
N4 C9 1.322(3) . ?
N4 C8 1.375(3) . ?
C8 C7 1.373(3) . ?
C6 C7 1.423(3) . ?
N6 C11 1.332(3) . ?
N6 C12 1.455(3) . ?
N6 H6 0.8800 . ?
C11 C10 1.515(3) . ?
N7 C14 1.370(4) . ?
N7 C17 1.394(4) . ?
N7 C13 1.453(3) . ?
C9 H9 0.9500 . ?
C4 C3 1.508(3) . ?
O5 C17 1.209(4) . ?
C12 C13 1.517(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C17 C16 1.480(4) . ?
C3 C2 1.504(4) . ?
C3 C1 1.505(5) . ?
C3 H3 1.0000 . ?
C16 C15 1.515(5) . ?
C16 C18 1.571(5) . ?
C16 H16 1.0000 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C14 O4 1.208(4) . ?
C14 C15 1.506(5) . ?
C15 C20 1.584(5) . ?
C15 H15 1.0000 . ?
C21 C22 1.307(6) . ?
C21 C20 1.504(6) . ?
C21 H21 0.9500 . ?
C20 C19 1.514(7) . ?
C20 H20 1.0000 . ?
C18 C22 1.486(6) . ?
C18 C19 1.544(7) . ?
C18 H18 1.0000 . ?
C22 H22 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
 
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
C5 N2 C6 125.01(18) . . ?
C5 N2 H2 117.5 . . ?
C6 N2 H2 117.5 . . ?
C4 N1 C5 127.95(19) . . ?
C4 N1 H1 116.0 . . ?
C5 N1 H1 116.0 . . ?
C9 N5 C7 105.68(17) . . ?
C9 N5 C10 125.59(18) . . ?
C7 N5 C10 128.40(18) . . ?
C5 N3 C8 112.80(17) . . ?
C9 N4 C8 103.72(17) . . ?
N3 C8 C7 125.16(19) . . ?
N3 C8 N4 124.13(18) . . ?
C7 C8 N4 110.71(18) . . ?
O2 C6 N2 121.23(19) . . ?
O2 C6 C7 129.4(2) . . ?
N2 C6 C7 109.40(17) . . ?
C8 C7 N5 105.82(17) . . ?
C8 C7 C6 122.14(19) . . ?
N5 C7 C6 132.02(19) . . ?
C11 N6 C12 122.50(19) . . ?
C11 N6 H6 118.8 . . ?
C12 N6 H6 118.8 . . ?
N3 C5 N2 125.39(19) . . ?
N3 C5 N1 117.31(18) . . ?
N2 C5 N1 117.30(18) . . ?
O3 C11 N6 123.6(2) . . ?
O3 C11 C10 123.13(19) . . ?
N6 C11 C10 113.28(19) . . ?
C14 N7 C17 112.5(3) . . ?
C14 N7 C13 125.1(2) . . ?
C17 N7 C13 121.7(2) . . ?
N4 C9 N5 114.06(19) . . ?
N4 C9 H9 123.0 . . ?
N5 C9 H9 123.0 . . ?
O1 C4 N1 122.6(2) . . ?
O1 C4 C3 123.3(2) . . ?
N1 C4 C3 114.0(2) . . ?
N6 C12 C13 112.7(2) . . ?
N6 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
N6 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
N5 C10 C11 113.26(18) . . ?
N5 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N5 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N7 C13 C12 112.7(2) . . ?
N7 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
N7 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
O5 C17 N7 123.3(3) . . ?
O5 C17 C16 127.9(3) . . ?
N7 C17 C16 108.7(3) . . ?
C2 C3 C1 112.6(3) . . ?
C2 C3 C4 112.0(2) . . ?
C1 C3 C4 108.3(3) . . ?
C2 C3 H3 107.9 . . ?
C1 C3 H3 107.9 . . ?
C4 C3 H3 107.9 . . ?
C17 C16 C15 105.5(3) . . ?
C17 C16 C18 113.4(3) . . ?
C15 C16 C18 103.2(3) . . ?
C17 C16 H16 111.5 . . ?
C15 C16 H16 111.5 . . ?
C18 C16 H16 111.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O4 C14 N7 123.1(3) . . ?
O4 C14 C15 128.5(4) . . ?
N7 C14 C15 108.4(3) . . ?
C14 C15 C16 104.9(3) . . ?
C14 C15 C20 113.2(3) . . ?
C16 C15 C20 103.1(3) . . ?
C14 C15 H15 111.7 . . ?
C16 C15 H15 111.7 . . ?
C20 C15 H15 111.7 . . ?
C22 C21 C20 108.0(4) . . ?
C22 C21 H21 126.0 . . ?
C20 C21 H21 126.0 . . ?
C21 C20 C19 100.1(4) . . ?
C21 C20 C15 106.3(3) . . ?
C19 C20 C15 99.1(4) . . ?
C21 C20 H20 116.3 . . ?
C19 C20 H20 116.3 . . ?
C15 C20 H20 116.3 . . ?
C22 C18 C19 100.6(4) . . ?
C22 C18 C16 106.9(3) . . ?
C19 C18 C16 98.5(3) . . ?
C22 C18 H18 116.1 . . ?
C19 C18 H18 116.1 . . ?
C16 C18 H18 116.1 . . ?
C21 C22 C18 108.1(4) . . ?
C21 C22 H22 126.0 . . ?
C18 C22 H22 126.0 . . ?
C20 C19 C18 93.8(3) . . ?
C20 C19 H19A 113.0 . . ?
C18 C19 H19A 113.0 . . ?
C20 C19 H19B 113.0 . . ?
C18 C19 H19B 113.0 . . ?
H19A C19 H19B 110.4 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              26.35
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.218
_refine_diff_density_min   -0.220
_refine_diff_density_rms    0.047
