 
data_bmarp 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C17 H21 N O4' 
_chemical_formula_weight          303.35 
 
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) 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
 
_cell_length_a                    11.335(9) 
_cell_length_b                    5.240(8) 
_cell_length_c                    13.442(10) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  104.10(5) 
_cell_angle_gamma                 90.00 
_cell_volume                      774.3(15) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     153(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           ? 
_exptl_crystal_size_mid           ? 
_exptl_crystal_size_min           ? 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.301 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              324 
_exptl_absorpt_coefficient_mu     0.093 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       153(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   ? 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             1329 
_diffrn_reflns_av_R_equivalents   0.0675 
_diffrn_reflns_av_sigmaI/netI     0.1248 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        12 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        6 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          2.11 
_diffrn_reflns_theta_max          30.36 
_reflns_number_total              1249 
_reflns_number_gt                 759 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_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)+(0.0590P)²+0.0000P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    4(5) 
_refine_ls_number_reflns          1249 
_refine_ls_number_parameters      202 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.1279 
_refine_ls_R_factor_gt            0.0608 
_refine_ls_wR_factor_ref          0.1466 
_refine_ls_wR_factor_gt           0.1195 
_refine_ls_goodness_of_fit_ref    1.002 
_refine_ls_restrained_S_all       1.002 
_refine_ls_shift/su_max           0.019 
_refine_ls_shift/su_mean          0.002 
 
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 -0.2658(6) -0.3750(14) -0.3364(5) 0.0240(18) Uani 1 1 d . . . 
H1N H -0.2727 -0.2197 -0.3621 0.029 Uiso 1 1 calc R . . 
C1 C -0.2269(7) -0.4115(19) -0.2264(5) 0.023(2) Uani 1 1 d . . . 
H1 H -0.2677 -0.5656 -0.2064 0.028 Uiso 1 1 calc R . . 
C2 C -0.0887(6) -0.4209(18) -0.1746(5) 0.023(2) Uani 1 1 d . . . 
H2 H -0.0556 -0.5964 -0.1569 0.027 Uiso 1 1 calc R . . 
C3 C -0.1188(7) -0.2712(18) -0.0830(6) 0.027(2) Uani 1 1 d . . . 
H3 H -0.0605 -0.1356 -0.0494 0.032 Uiso 1 1 calc R . . 
O4 O -0.1638(5) -0.4438(12) -0.0180(4) 0.0290(16) Uani 1 1 d . . . 
C5 C -0.2763(7) -0.3359(17) -0.0060(6) 0.025(2) Uani 1 1 d . . . 
O6 O -0.3296(5) -0.2037(12) -0.0986(3) 0.0266(15) Uani 1 1 d . . . 
C7 C -0.2392(7) -0.1855(17) -0.1557(5) 0.022(2) Uani 1 1 d . . . 
H7 H -0.2349 -0.0142 -0.1874 0.026 Uiso 1 1 calc R . . 
C8 C -0.0138(7) -0.2570(17) -0.2284(6) 0.025(2) Uani 1 1 d . . . 
H8A H 0.0611 -0.2024 -0.1781 0.029 Uiso 1 1 calc R . . 
H8B H -0.0607 -0.1018 -0.2551 0.029 Uiso 1 1 calc R . . 
O9 O 0.0099(6) -0.6254(14) -0.3275(5) 0.0436(19) Uani 1 1 d . . . 
C9 C 0.0218(8) -0.396(2) -0.3179(7) 0.032(2) Uani 1 1 d . . . 
C10 C 0.0783(9) -0.232(2) -0.3844(7) 0.048(3) Uani 1 1 d . . . 
H10A H 0.0711 -0.3154 -0.4508 0.072 Uiso 1 1 calc R . . 
H10B H 0.1644 -0.2047 -0.3511 0.072 Uiso 1 1 calc R . . 
H10C H 0.0364 -0.0666 -0.3951 0.072 Uiso 1 1 calc R . . 
O11 O -0.2839(6) -0.7989(12) -0.3675(4) 0.0302(16) Uani 1 1 d . . . 
C11 C -0.2914(7) -0.5787(18) -0.3997(6) 0.023(2) Uani 1 1 d . . . 
C12 C -0.3331(7) -0.5218(17) -0.5125(6) 0.020(2) Uani 1 1 d . . . 
C13 C -0.2951(8) -0.3070(18) -0.5559(6) 0.033(2) Uani 1 1 d . . . 
H13 H -0.2410 -0.1901 -0.5138 0.040 Uiso 1 1 calc R . . 
C14 C -0.3360(8) -0.2600(19) -0.6620(6) 0.038(3) Uani 1 1 d . . . 
H14 H -0.3094 -0.1139 -0.6923 0.046 Uiso 1 1 calc R . . 
C15 C -0.4162(8) -0.433(2) -0.7208(6) 0.036(3) Uani 1 1 d . . . 
H15 H -0.4454 -0.4040 -0.7923 0.044 Uiso 1 1 calc R . . 
C16 C -0.4545(7) -0.647(2) -0.6777(6) 0.036(3) Uani 1 1 d . . . 
H16 H -0.5086 -0.7652 -0.7193 0.044 Uiso 1 1 calc R . . 
C17 C -0.4133(7) -0.6891(19) -0.5727(6) 0.024(2) Uani 1 1 d . . . 
H17 H -0.4407 -0.8342 -0.5424 0.029 Uiso 1 1 calc R . . 
C18 C -0.2510(8) -0.159(2) 0.0841(6) 0.040(3) Uani 1 1 d . . . 
H18A H -0.2054 -0.0105 0.0692 0.059 Uiso 1 1 calc R . . 
H18B H -0.2030 -0.2479 0.1446 0.059 Uiso 1 1 calc R . . 
H18C H -0.3281 -0.1016 0.0974 0.059 Uiso 1 1 calc R . . 
C19 C -0.3607(8) -0.5528(19) 0.0049(7) 0.039(3) Uani 1 1 d . . . 
H19A H -0.3676 -0.6720 -0.0524 0.058 Uiso 1 1 calc R . . 
H19B H -0.4413 -0.4842 0.0044 0.058 Uiso 1 1 calc R . . 
H19C H -0.3279 -0.6425 0.0697 0.058 Uiso 1 1 calc R . . 
 
 
_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 C11 1.351(11) . ? 
N1 C1 1.449(9) . ? 
C1 C7 1.545(11) . ? 
C1 C2 1.552(10) . ? 
C2 C8 1.510(11) . ? 
C2 C3 1.565(11) . ? 
C3 O4 1.435(10) . ? 
C3 C7 1.539(11) . ? 
O4 C5 1.440(9) . ? 
C5 O6 1.424(9) . ? 
C5 C18 1.497(11) . ? 
C5 C19 1.516(12) . ? 
O6 C7 1.426(8) . ? 
C8 C9 1.542(12) . ? 
O9 C9 1.212(12) . ? 
C9 C10 1.495(12) . ? 
O11 C11 1.228(10) . ? 
C11 C12 1.505(10) . ? 
C12 C17 1.375(11) . ? 
C12 C13 1.384(12) . ? 
C13 C14 1.410(11) . ? 
C14 C15 1.388(12) . ? 
C15 C16 1.380(13) . ? 
C16 C17 1.391(10) . ? 
 
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 
C11 N1 C1 120.2(7) . . ? 
N1 C1 C7 118.4(7) . . ? 
N1 C1 C2 119.0(6) . . ? 
C7 C1 C2 88.9(6) . . ? 
C8 C2 C1 113.0(6) . . ? 
C8 C2 C3 110.3(7) . . ? 
C1 C2 C3 87.0(6) . . ? 
O4 C3 C7 100.3(6) . . ? 
O4 C3 C2 109.9(7) . . ? 
C7 C3 C2 88.6(6) . . ? 
C3 O4 C5 106.1(6) . . ? 
O6 C5 O4 107.0(6) . . ? 
O6 C5 C18 111.2(7) . . ? 
O4 C5 C18 109.5(6) . . ? 
O6 C5 C19 107.8(7) . . ? 
O4 C5 C19 108.3(7) . . ? 
C18 C5 C19 112.8(7) . . ? 
C5 O6 C7 107.2(6) . . ? 
O6 C7 C3 106.3(6) . . ? 
O6 C7 C1 117.7(7) . . ? 
C3 C7 C1 88.2(6) . . ? 
C2 C8 C9 112.9(7) . . ? 
O9 C9 C10 124.1(10) . . ? 
O9 C9 C8 120.6(9) . . ? 
C10 C9 C8 115.2(9) . . ? 
O11 C11 N1 122.3(8) . . ? 
O11 C11 C12 121.3(8) . . ? 
N1 C11 C12 116.4(8) . . ? 
C17 C12 C13 120.0(8) . . ? 
C17 C12 C11 117.9(8) . . ? 
C13 C12 C11 122.1(8) . . ? 
C12 C13 C14 120.6(9) . . ? 
C15 C14 C13 118.0(9) . . ? 
C16 C15 C14 121.5(8) . . ? 
C15 C16 C17 119.4(9) . . ? 
C12 C17 C16 120.5(9) . . ? 
 
_diffrn_measured_fraction_theta_max    0.487 
_diffrn_reflns_theta_full              30.36 
_diffrn_measured_fraction_theta_full   0.487 
_refine_diff_density_max    0.272 
_refine_diff_density_min   -0.283 
_refine_diff_density_rms    0.066 
