 
data_04src0988r
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C22 H26 N2 O4'
_chemical_formula_sum
 'C22 H26 N2 O4'
_chemical_formula_weight          382.45
 
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    C2/c
_symmetry_space_group_name_hall   '-C 2yc'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    41.67(2)
_cell_length_b                    4.965(3)
_cell_length_c                    9.731(7)
_cell_angle_alpha                 90.00
_cell_angle_beta                  101.49(8)
_cell_angle_gamma                 90.00
_cell_volume                      1973(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2364
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.26
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.288
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              816
_exptl_absorpt_coefficient_mu     0.089
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9773
_exptl_absorpt_correction_T_max   0.9996
_exptl_absorpt_process_details    'SADABS V2.10 (Sheldrick, G.M., 2003)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   '10cm confocal mirrors'
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          none
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         negligible
_diffrn_reflns_number             8886
_diffrn_reflns_av_R_equivalents   0.0807
_diffrn_reflns_av_sigmaI/netI     0.0756
_diffrn_reflns_limit_h_min        -51
_diffrn_reflns_limit_h_max        54
_diffrn_reflns_limit_k_min        -6
_diffrn_reflns_limit_k_max        5
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          2.99
_diffrn_reflns_theta_max          27.50
_reflns_number_total              2253
_reflns_number_gt                 1719
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        'DENZO, COLLECT'
_computing_data_reduction         'DENZO, COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 1990)'
_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 > 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)+(0.0375P)²+21.9223P] 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      SHELXL
_refine_ls_extinction_coef        0.0056(11)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          2253
_refine_ls_number_parameters      136
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1422
_refine_ls_R_factor_gt            0.1155
_refine_ls_wR_factor_ref          0.2709
_refine_ls_wR_factor_gt           0.2596
_refine_ls_goodness_of_fit_ref    1.207
_refine_ls_restrained_S_all       1.207
_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
C1 C 0.48592(12) 0.4359(10) 1.4844(5) 0.0250(10) Uani 1 1 d . . .
C2 C 0.45982(11) 0.4851(10) 1.3572(5) 0.0260(10) Uani 1 1 d . . .
H2A H 0.4673 0.6273 1.2996 0.031 Uiso 1 1 calc R . .
H2B H 0.4399 0.5521 1.3872 0.031 Uiso 1 1 calc R . .
C3 C 0.45109(11) 0.2364(10) 1.2680(5) 0.0233(10) Uani 1 1 d . . .
H3A H 0.4702 0.1794 1.2287 0.028 Uiso 1 1 calc R . .
H3B H 0.4454 0.0878 1.3267 0.028 Uiso 1 1 calc R . .
C4 C 0.40862(10) 0.0934(9) 1.0721(5) 0.0201(9) Uani 1 1 d . . .
C5 C 0.36580(12) -0.0082(10) 0.8781(5) 0.0277(11) Uani 1 1 d . . .
H5A H 0.3572 -0.1514 0.9318 0.033 Uiso 1 1 calc R . .
H5B H 0.3802 -0.0920 0.8206 0.033 Uiso 1 1 calc R . .
C6 C 0.33814(11) 0.1384(10) 0.7864(5) 0.0228(10) Uani 1 1 d . . .
C7 C 0.34410(12) 0.3424(10) 0.6971(5) 0.0291(11) Uani 1 1 d . . .
H7 H 0.3660 0.3911 0.6948 0.035 Uiso 1 1 calc R . .
C8 C 0.31878(13) 0.4747(11) 0.6120(5) 0.0313(11) Uani 1 1 d . . .
H8 H 0.3233 0.6124 0.5508 0.038 Uiso 1 1 calc R . .
C9 C 0.28674(12) 0.4080(11) 0.6152(5) 0.0320(12) Uani 1 1 d . . .
H9 H 0.2692 0.4994 0.5563 0.038 Uiso 1 1 calc R . .
C10 C 0.28041(12) 0.2078(11) 0.7045(6) 0.0338(12) Uani 1 1 d . . .
H10 H 0.2584 0.1624 0.7073 0.041 Uiso 1 1 calc R . .
C11 C 0.30573(12) 0.0731(11) 0.7896(5) 0.0291(11) Uani 1 1 d . . .
H11 H 0.3011 -0.0646 0.8506 0.035 Uiso 1 1 calc R . .
N1 N 0.42346(9) 0.2915(8) 1.1544(4) 0.0218(9) Uani 1 1 d . . .
O1 O 0.41565(8) -0.1446(7) 1.0851(4) 0.0274(8) Uani 1 1 d . . .
O2 O 0.38389(8) 0.1912(7) 0.9730(3) 0.0247(8) Uani 1 1 d . . .
H1N H 0.4172(12) 0.472(11) 1.127(5) 0.023(13) Uiso 1 1 d . . .
H1 H 0.4823(12) 0.298(12) 1.540(5) 0.023(13) 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
C1 0.029(2) 0.021(2) 0.024(2) 0.0026(19) 0.0050(19) 0.0008(19)
C2 0.024(2) 0.025(2) 0.027(2) -0.0025(19) -0.0003(18) 0.0009(19)
C3 0.020(2) 0.024(2) 0.024(2) 0.0006(19) -0.0004(18) 0.0015(18)
C4 0.019(2) 0.020(2) 0.020(2) 0.0021(17) 0.0013(16) 0.0007(17)
C5 0.027(2) 0.021(2) 0.033(3) -0.007(2) -0.001(2) -0.0007(19)
C6 0.024(2) 0.023(2) 0.022(2) -0.0076(19) 0.0042(18) -0.0022(18)
C7 0.025(2) 0.030(3) 0.032(3) -0.002(2) 0.006(2) -0.002(2)
C8 0.037(3) 0.029(3) 0.027(2) 0.003(2) 0.004(2) 0.000(2)
C9 0.028(2) 0.032(3) 0.032(3) -0.001(2) -0.004(2) 0.006(2)
C10 0.022(2) 0.037(3) 0.041(3) -0.002(2) 0.004(2) -0.004(2)
C11 0.026(2) 0.028(3) 0.033(3) 0.000(2) 0.006(2) -0.008(2)
N1 0.0212(18) 0.0167(19) 0.024(2) -0.0001(15) -0.0040(15) 0.0017(15)
O1 0.0309(18) 0.0177(17) 0.0301(18) -0.0011(14) -0.0026(14) 0.0008(14)
O2 0.0238(16) 0.0221(17) 0.0247(16) -0.0039(13) -0.0040(13) 0.0005(13)
 
_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
C1 C1 1.316(10) 5_668 ?
C1 C2 1.496(7) . ?
C1 H1 0.91(6) . ?
C2 C3 1.511(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N1 1.455(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O1 1.217(6) . ?
C4 N1 1.339(6) . ?
C4 O2 1.353(5) . ?
C5 O2 1.457(6) . ?
C5 C6 1.498(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.389(7) . ?
C6 C11 1.395(6) . ?
C7 C8 1.372(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(7) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
N1 H1N 0.95(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
C1 C1 C2 125.5(6) 5_668 . ?
C1 C1 H1 118(3) 5_668 . ?
C2 C1 H1 116(3) . . ?
C1 C2 C3 113.2(4) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
N1 C3 C2 110.3(4) . . ?
N1 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
N1 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
O1 C4 N1 125.3(4) . . ?
O1 C4 O2 123.7(4) . . ?
N1 C4 O2 110.9(4) . . ?
O2 C5 C6 106.7(4) . . ?
O2 C5 H5A 110.4 . . ?
C6 C5 H5A 110.4 . . ?
O2 C5 H5B 110.4 . . ?
C6 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
C7 C6 C11 118.5(5) . . ?
C7 C6 C5 121.0(4) . . ?
C11 C6 C5 120.5(4) . . ?
C8 C7 C6 121.0(5) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 120.2(5) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 119.6(5) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 120.6(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C6 120.2(5) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
C4 N1 C3 121.2(4) . . ?
C4 N1 H1N 117(3) . . ?
C3 N1 H1N 121(3) . . ?
C4 O2 C5 115.6(4) . . ?
 
_diffrn_measured_fraction_theta_max    0.992
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    0.422
_refine_diff_density_min   -0.331
_refine_diff_density_rms    0.093
