# Copyright The Royal Society of Chemistry, 1999
# CCDC Number: 186/1326

data_jcb2 
  
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      JCB2 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C44 H56 N8 O4' 
_chemical_formula_weight          760.97 
_chemical_melting_point           ? 
_chemical_compound_source         ? 
  
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                    13.0360(11) 
_cell_length_b                    16.1964(14) 
_cell_length_c                    9.7490(9) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  97.117(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      2042.5(3) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     1610 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
  
_exptl_crystal_description        plate 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.06 
_exptl_crystal_size_mid           0.18 
_exptl_crystal_size_min           0.22 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.237 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              816 
_exptl_absorpt_coefficient_mu     0.081 
_exptl_absorpt_correction_type    SADABS 
_exptl_absorpt_correction_T_min   0.82 
_exptl_absorpt_correction_T_max   0.97 
  
_exptl_special_details 
; 
? 
; 
  
_diffrn_ambient_temperature       173(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        'Siemens P4' 
_diffrn_measurement_method        '\w scans' 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             10230 
_diffrn_reflns_av_R_equivalents   0.1091 
_diffrn_reflns_av_sigmaI/netI     0.1449 
_diffrn_reflns_limit_h_min        -13 
_diffrn_reflns_limit_h_max        15 
_diffrn_reflns_limit_k_min        -18 
_diffrn_reflns_limit_k_max        19 
_diffrn_reflns_limit_l_min        -7 
_diffrn_reflns_limit_l_max        11 
_diffrn_reflns_theta_min          1.57 
_diffrn_reflns_theta_max          24.68 
_reflns_number_total              3461 
_reflns_number_observed           1716 
_reflns_observed_criterion        >2sigma(I) 
  
_computing_data_collection        'Siemens XSCANS' 
_computing_cell_refinement        'Siemens XSCANS' 
_computing_data_reduction         'Siemens SHELXTL' 
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     'Siemens SHELXTL' 
_computing_publication_material   'Siemens SHELXTL' 
  
_refine_special_details 
; 
Refinement on F^2^ for ALL reflections except for 559 with very negative F^2^ 
or flagged by the user for potential systematic errors.  Weighted R-factors 
wR and all goodnesses 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 observed criterion 
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 
'0.0548, 0.0000' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     ? 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0134(16) 
_refine_ls_extinction_expression 
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_number_reflns          2902 
_refine_ls_number_parameters      254 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1815 
_refine_ls_R_factor_obs           0.0733 
_refine_ls_wR_factor_all          0.1732 
_refine_ls_wR_factor_obs          0.1174 
_refine_ls_goodness_of_fit_all    1.027 
_refine_ls_goodness_of_fit_obs    1.183 
_refine_ls_restrained_S_all       1.185 
_refine_ls_restrained_S_obs       1.183 
_refine_ls_shift/esd_max          0.001 
_refine_ls_shift/esd_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_thermal_displace_type 
_atom_site_occupancy 
_atom_site_calc_flag 
_atom_site_refinement_flags 
_atom_site_disorder_group 
O1 O 0.2756(2) -0.2383(2) 0.6513(3) 0.0404(8) Uani 1 d . . 
O2 O 0.5954(2) -0.1485(2) 0.0992(3) 0.0413(8) Uani 1 d . . 
N1 N 0.4328(2) -0.1339(2) 0.5344(3) 0.0239(8) Uani 1 d . . 
N2 N 0.4472(2) -0.0116(2) 0.2988(3) 0.0260(8) Uani 1 d . . 
N3 N 0.2278(2) -0.2769(2) 0.4297(3) 0.0297(8) Uani 1 d . . 
H3A H 0.2450(2) -0.2774(2) 0.3292(3) 0.036 Uiso 1 d R . 
N4 N 0.5839(2) -0.1407(2) 0.3300(3) 0.0308(8) Uani 1 d . . 
H4A H 0.5413(2) -0.1178(2) 0.4042(3) 0.037 Uiso 1 d R . 
C1 C 0.3565(3) -0.0700(2) 0.4857(4) 0.0279(10) Uani 1 d . . 
H1A H 0.3745(3) -0.0180(2) 0.5364(4) 0.033 Uiso 1 calc R . 
H1B H 0.2873(3) -0.0875(2) 0.5064(4) 0.033 Uiso 1 calc R . 
C2 C 0.3526(3) -0.0543(2) 0.3308(4) 0.0306(10) Uani 1 d . . 
H2A H 0.3455(3) -0.1076(2) 0.2808(4) 0.037 Uiso 1 calc R . 
H2B H 0.2914(3) -0.0201(2) 0.2987(4) 0.037 Uiso 1 calc R . 
C3 C 0.4314(3) 0.0783(2) 0.2879(4) 0.0290(10) Uani 1 d . . 
H3B H 0.3828(3) 0.0950(2) 0.3532(4) 0.035 Uiso 1 calc R . 
H3C H 0.3985(3) 0.0914(2) 0.1934(4) 0.035 Uiso 1 calc R . 
C4 C 0.5296(3) 0.1294(2) 0.3178(4) 0.0289(10) Uani 1 d . . 
H4B H 0.5841(3) 0.1049(2) 0.2683(4) 0.035 Uiso 1 calc R . 
H4C H 0.5161(3) 0.1860(2) 0.2817(4) 0.035 Uiso 1 calc R . 
C5 C 0.3974(3) -0.2159(2) 0.4889(4) 0.0250(9) Uani 1 d . . 
H5A H 0.4509(3) -0.2563(2) 0.5254(4) 0.030 Uiso 1 calc R . 
H5B H 0.3924(3) -0.2177(2) 0.3868(4) 0.030 Uiso 1 calc R . 
C6 C 0.2942(3) -0.2441(2) 0.5309(4) 0.0270(10) Uani 1 d . . 
C7 C 0.1311(3) -0.3133(2) 0.4577(4) 0.0364(11) Uani 1 d . . 
H7A H 0.0825(3) -0.3133(2) 0.3712(4) 0.044 Uiso 1 calc R . 
H7B H 0.1008(3) -0.2781(2) 0.5254(4) 0.044 Uiso 1 calc R . 
C8 C 0.1403(3) -0.4003(2) 0.5131(4) 0.0284(10) Uani 1 d . . 
C9 C 0.0847(3) -0.4255(2) 0.6174(4) 0.0367(11) Uani 1 d . . 
H9A H 0.0429(3) -0.3868(2) 0.6582(4) 0.044 Uiso 1 calc R . 
C10 C 0.0892(3) -0.5066(3) 0.6631(5) 0.0415(12) Uani 1 d . . 
H10A H 0.0500(3) -0.5229(3) 0.7345(5) 0.050 Uiso 1 calc R . 
C11 C 0.1497(3) -0.5637(2) 0.6065(5) 0.0388(11) Uani 1 d . . 
H11A H 0.1524(3) -0.6192(2) 0.6379(5) 0.047 Uiso 1 calc R . 
C12 C 0.2064(3) -0.5391(3) 0.5037(4) 0.0407(11) Uani 1 d . . 
H12A H 0.2492(3) -0.5779(3) 0.4649(4) 0.049 Uiso 1 calc R . 
C13 C 0.2017(3) -0.4584(2) 0.4560(4) 0.0333(10) Uani 1 d . . 
H13A H 0.2406(3) -0.4425(2) 0.3841(4) 0.040 Uiso 1 calc R . 
C14 C 0.4863(3) -0.0439(2) 0.1755(4) 0.0311(10) Uani 1 d . . 
H14A H 0.5222(3) 0.0013(2) 0.1327(4) 0.037 Uiso 1 calc R . 
H14B H 0.4265(3) -0.0606(2) 0.1086(4) 0.037 Uiso 1 calc R . 
C15 C 0.5594(3) -0.1165(2) 0.1981(4) 0.0312(10) Uani 1 d . . 
C16 C 0.6544(3) -0.2097(2) 0.3688(4) 0.0345(11) Uani 1 d . . 
H16A H 0.6618(3) -0.2429(2) 0.2853(4) 0.041 Uiso 1 calc R . 
H16B H 0.6236(3) -0.2456(2) 0.4349(4) 0.041 Uiso 1 calc R . 
C17 C 0.7594(3) -0.1830(2) 0.4327(4) 0.0296(10) Uani 1 d . . 
C18 C 0.8081(3) -0.2248(2) 0.5470(4) 0.0376(11) Uani 1 d . . 
H18A H 0.7724(3) -0.2679(2) 0.5870(4) 0.045 Uiso 1 calc R . 
C19 C 0.9073(4) -0.2049(3) 0.6037(5) 0.0530(14) Uani 1 d . . 
H19A H 0.9389(4) -0.2346(3) 0.6818(5) 0.064 Uiso 1 calc R . 
C20 C 0.9607(4) -0.1428(3) 0.5487(6) 0.0582(15) Uani 1 d . . 
H20A H 1.0292(4) -0.1295(3) 0.5873(6) 0.070 Uiso 1 calc R . 
C21 C 0.9131(4) -0.1000(3) 0.4363(6) 0.0582(15) Uani 1 d . . 
H21A H 0.9490(4) -0.0565(3) 0.3976(6) 0.070 Uiso 1 calc R . 
C22 C 0.8132(3) -0.1197(3) 0.3788(5) 0.0468(12) Uani 1 d . . 
H22A H 0.7816(3) -0.0893(3) 0.3015(5) 0.056 Uiso 1 calc R . 
  
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 
O1 0.053(2) 0.051(2) 0.019(2) -0.0038(14) 0.0125(15) -0.0123(14) 
O2 0.053(2) 0.042(2) 0.032(2) -0.0107(14) 0.016(2) -0.0060(14) 
N1 0.030(2) 0.020(2) 0.021(2) 0.0008(15) 0.000(2) -0.0003(14) 
N2 0.040(2) 0.021(2) 0.017(2) -0.0005(14) 0.002(2) -0.0005(14) 
N3 0.035(2) 0.039(2) 0.016(2) -0.002(2) 0.003(2) -0.008(2) 
N4 0.034(2) 0.032(2) 0.027(2) 0.000(2) 0.009(2) 0.004(2) 
C1 0.033(2) 0.021(2) 0.029(2) 0.001(2) 0.000(2) 0.000(2) 
C2 0.036(3) 0.024(2) 0.030(3) 0.003(2) -0.005(2) -0.006(2) 
C3 0.035(2) 0.023(2) 0.027(2) 0.005(2) -0.001(2) 0.005(2) 
C4 0.040(3) 0.024(2) 0.022(2) 0.004(2) 0.000(2) -0.002(2) 
C5 0.034(2) 0.023(2) 0.018(2) 0.001(2) 0.005(2) -0.002(2) 
C6 0.040(3) 0.017(2) 0.025(3) 0.001(2) 0.005(2) 0.000(2) 
C7 0.030(3) 0.041(3) 0.037(3) 0.000(2) -0.001(2) -0.003(2) 
C8 0.022(2) 0.034(2) 0.028(3) -0.005(2) -0.001(2) -0.007(2) 
C9 0.032(3) 0.039(3) 0.041(3) -0.001(2) 0.008(2) 0.002(2) 
C10 0.041(3) 0.041(3) 0.044(3) 0.002(2) 0.008(2) -0.007(2) 
C11 0.041(3) 0.032(2) 0.043(3) 0.001(2) 0.002(2) -0.006(2) 
C12 0.039(3) 0.038(3) 0.044(3) -0.008(2) 0.002(2) 0.001(2) 
C13 0.035(3) 0.038(3) 0.028(3) -0.003(2) 0.009(2) -0.007(2) 
C14 0.042(3) 0.029(2) 0.021(2) 0.001(2) -0.001(2) -0.004(2) 
C15 0.037(3) 0.029(2) 0.027(3) -0.001(2) 0.006(2) -0.013(2) 
C16 0.033(3) 0.033(2) 0.039(3) 0.001(2) 0.010(2) -0.001(2) 
C17 0.032(3) 0.026(2) 0.033(3) -0.002(2) 0.013(2) 0.000(2) 
C18 0.042(3) 0.028(2) 0.044(3) -0.009(2) 0.011(3) 0.003(2) 
C19 0.046(3) 0.043(3) 0.067(4) -0.007(3) -0.003(3) 0.010(2) 
C20 0.042(3) 0.055(3) 0.076(4) -0.034(3) -0.001(3) 0.001(3) 
C21 0.059(4) 0.054(3) 0.066(4) -0.014(3) 0.027(3) -0.024(3) 
C22 0.048(3) 0.049(3) 0.043(3) 0.000(2) 0.006(3) -0.014(2) 
  
_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 
O1 C6 1.232(4) . ? 
O2 C15 1.237(4) . ? 
N1 C5 1.457(4) . ? 
N1 C4 1.466(4) 3_656 ? 
N1 C1 1.473(4) . ? 
N2 C14 1.459(4) . ? 
N2 C3 1.474(4) . ? 
N2 C2 1.480(4) . ? 
N3 C6 1.339(4) . ? 
N3 C7 1.448(4) . ? 
N4 C15 1.344(5) . ? 
N4 C16 1.467(4) . ? 
C1 C2 1.526(5) . ? 
C3 C4 1.522(5) . ? 
C4 N1 1.466(4) 3_656 ? 
C5 C6 1.524(5) . ? 
C7 C8 1.508(5) . ? 
C8 C9 1.381(5) . ? 
C8 C13 1.395(5) . ? 
C9 C10 1.385(5) . ? 
C10 C11 1.375(5) . ? 
C11 C12 1.375(5) . ? 
C12 C13 1.387(5) . ? 
C14 C15 1.512(5) . ? 
C16 C17 1.496(5) . ? 
C17 C22 1.382(5) . ? 
C17 C18 1.388(5) . ? 
C18 C19 1.380(5) . ? 
C19 C20 1.369(6) . ? 
C20 C21 1.377(6) . ? 
C21 C22 1.389(6) . ? 
  
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 N1 C4 113.5(3) . 3_656 ? 
C5 N1 C1 111.5(3) . . ? 
C4 N1 C1 114.3(3) 3_656 . ? 
C14 N2 C3 110.8(3) . . ? 
C14 N2 C2 113.0(3) . . ? 
C3 N2 C2 111.4(3) . . ? 
C6 N3 C7 121.4(3) . . ? 
C15 N4 C16 122.4(3) . . ? 
N1 C1 C2 111.9(3) . . ? 
N2 C2 C1 111.1(3) . . ? 
N2 C3 C4 114.6(3) . . ? 
N1 C4 C3 112.7(3) 3_656 . ? 
N1 C5 C6 116.7(3) . . ? 
O1 C6 N3 123.2(3) . . ? 
O1 C6 C5 121.2(4) . . ? 
N3 C6 C5 115.6(3) . . ? 
N3 C7 C8 114.5(3) . . ? 
C9 C8 C13 118.3(4) . . ? 
C9 C8 C7 120.9(3) . . ? 
C13 C8 C7 120.7(4) . . ? 
C8 C9 C10 120.8(4) . . ? 
C11 C10 C9 120.7(4) . . ? 
C12 C11 C10 119.0(4) . . ? 
C11 C12 C13 120.8(4) . . ? 
C12 C13 C8 120.4(4) . . ? 
N2 C14 C15 115.9(3) . . ? 
O2 C15 N4 123.7(4) . . ? 
O2 C15 C14 120.4(4) . . ? 
N4 C15 C14 115.9(4) . . ? 
N4 C16 C17 113.5(3) . . ? 
C22 C17 C18 117.6(4) . . ? 
C22 C17 C16 122.5(4) . . ? 
C18 C17 C16 119.8(4) . . ? 
C19 C18 C17 121.4(4) . . ? 
C20 C19 C18 120.7(5) . . ? 
C19 C20 C21 118.7(5) . . ? 
C20 C21 C22 120.9(5) . . ? 
C17 C22 C21 120.7(4) . . ? 
  
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 
N1 C1 C2 C3 -107.5(3) . . . . ? 
C1 C2 C3 C4 56.0(5) . . . . ? 
C2 C3 C4 N1 -51.3(6) . . . 3_656 ? 
C3 C4 N1 C1 92.6(4) . . 3_656 3_656 ? 
C4 N1 C1 C2 -156.8(3) . 3_656 3_656 3_656 ? 
  
_refine_diff_density_max    0.213 
_refine_diff_density_min   -0.208 
_refine_diff_density_rms    0.052