data_2005src0502
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C21 H27 N O4'
_chemical_formula_sum
 'C21 H27 N O4'
_chemical_formula_weight          357.44
 
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
_symmetry_space_group_name_hall   '-P 2ybc'
 
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                    14.5879(19)
_cell_length_b                    10.4825(9)
_cell_length_c                    12.641(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  91.815(16)
_cell_angle_gamma                 90.00
_cell_volume                      1932.1(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     4268
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.34
_exptl_crystal_size_mid           0.30
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.229
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              768
_exptl_absorpt_coefficient_mu     0.084
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9719
_exptl_absorpt_correction_T_max   0.9992
_exptl_absorpt_process_details    'SADABS V2.10 (Sheldrick, G.M., 2003)'
 
_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   '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             18917
_diffrn_reflns_av_R_equivalents   0.0757
_diffrn_reflns_av_sigmaI/netI     0.0692
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        18
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          2.91
_diffrn_reflns_theta_max          27.50
_reflns_number_total              4288
_reflns_number_gt                 2899
_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 > 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)+(0.0545P)²+1.1530P] 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
_refine_ls_number_reflns          4288
_refine_ls_number_parameters      246
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1023
_refine_ls_R_factor_gt            0.0615
_refine_ls_wR_factor_ref          0.1516
_refine_ls_wR_factor_gt           0.1343
_refine_ls_goodness_of_fit_ref    1.032
_refine_ls_restrained_S_all       1.032
_refine_ls_shift/su_max           0.002
_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 0.50871(16) 0.4528(2) 0.1624(2) 0.0386(6) Uani 1 1 d . . .
H1A H 0.4677 0.3818 0.1785 0.058 Uiso 1 1 calc R . .
H1B H 0.4795 0.5071 0.1079 0.058 Uiso 1 1 calc R . .
H1C H 0.5211 0.5031 0.2266 0.058 Uiso 1 1 calc R . .
C2 C 0.64099(16) 0.3201(2) 0.18870(19) 0.0314(5) Uani 1 1 d . . .
C3 C 0.61052(15) 0.2729(2) 0.28431(19) 0.0318(5) Uani 1 1 d . . .
H3 H 0.5537 0.3002 0.3111 0.038 Uiso 1 1 calc R . .
C4 C 0.66517(15) 0.1845(2) 0.34018(18) 0.0295(5) Uani 1 1 d . . .
H4 H 0.6445 0.1520 0.4054 0.035 Uiso 1 1 calc R . .
C5 C 0.74808(14) 0.1433(2) 0.30361(17) 0.0265(5) Uani 1 1 d . . .
C6 C 0.77807(15) 0.1940(2) 0.20978(18) 0.0298(5) Uani 1 1 d . . .
H6 H 0.8356 0.1681 0.1839 0.036 Uiso 1 1 calc R . .
C7 C 0.72551(15) 0.2819(2) 0.15307(19) 0.0323(5) Uani 1 1 d . . .
H7 H 0.7476 0.3164 0.0892 0.039 Uiso 1 1 calc R . .
C8 C 0.80288(14) 0.0398(2) 0.36201(18) 0.0275(5) Uani 1 1 d . . .
H8 H 0.7842 0.0425 0.4374 0.033 Uiso 1 1 calc R . .
C9 C 0.90634(15) 0.0615(2) 0.36313(17) 0.0276(5) Uani 1 1 d . . .
C10 C 0.96539(16) -0.0142(2) 0.30622(19) 0.0327(5) Uani 1 1 d . . .
H10 H 0.9415 -0.0808 0.2624 0.039 Uiso 1 1 calc R . .
C11 C 1.05898(16) 0.0071(2) 0.31332(19) 0.0362(6) Uani 1 1 d . . .
H11 H 1.0988 -0.0445 0.2734 0.043 Uiso 1 1 calc R . .
C12 C 1.09560(16) 0.1023(2) 0.37762(19) 0.0323(5) Uani 1 1 d . . .
H12 H 1.1601 0.1149 0.3819 0.039 Uiso 1 1 calc R . .
C13 C 1.03855(15) 0.17958(19) 0.43590(17) 0.0264(5) Uani 1 1 d . . .
C14 C 0.94410(14) 0.1590(2) 0.42616(17) 0.0259(5) Uani 1 1 d . . .
C15 C 0.86680(16) 0.3573(2) 0.4461(2) 0.0337(5) Uani 1 1 d . . .
H15A H 0.9233 0.3953 0.4205 0.050 Uiso 1 1 calc R . .
H15B H 0.8428 0.4106 0.5026 0.050 Uiso 1 1 calc R . .
H15C H 0.8212 0.3517 0.3877 0.050 Uiso 1 1 calc R . .
C16 C 1.07427(15) 0.2803(2) 0.51293(18) 0.0306(5) Uani 1 1 d . . .
H16A H 1.0547 0.3651 0.4864 0.037 Uiso 1 1 calc R . .
H16B H 1.0454 0.2667 0.5819 0.037 Uiso 1 1 calc R . .
C17 C 1.22771(15) 0.34349(19) 0.46426(17) 0.0259(5) Uani 1 1 d . . .
C18 C 1.33146(15) 0.3396(2) 0.48912(18) 0.0293(5) Uani 1 1 d . . .
C19 C 1.36688(17) 0.2098(2) 0.4520(2) 0.0425(6) Uani 1 1 d . . .
H19A H 1.3366 0.1415 0.4908 0.064 Uiso 1 1 calc R . .
H19B H 1.4333 0.2050 0.4655 0.064 Uiso 1 1 calc R . .
H19C H 1.3533 0.2000 0.3760 0.064 Uiso 1 1 calc R . .
C20 C 1.35348(17) 0.3575(2) 0.6072(2) 0.0395(6) Uani 1 1 d . . .
H20A H 1.3266 0.4378 0.6312 0.059 Uiso 1 1 calc R . .
H20B H 1.4201 0.3600 0.6194 0.059 Uiso 1 1 calc R . .
H20C H 1.3278 0.2863 0.6468 0.059 Uiso 1 1 calc R . .
C21 C 1.37720(17) 0.4458(3) 0.4265(2) 0.0481(7) Uani 1 1 d . . .
H21A H 1.3619 0.4354 0.3510 0.072 Uiso 1 1 calc R . .
H21B H 1.4439 0.4412 0.4381 0.072 Uiso 1 1 calc R . .
H21C H 1.3551 0.5289 0.4505 0.072 Uiso 1 1 calc R . .
N1 N 1.17339(13) 0.28135(18) 0.53010(16) 0.0287(4) Uani 1 1 d . . .
O1 O 0.59265(11) 0.40387(15) 0.12469(14) 0.0405(4) Uani 1 1 d . . .
O2 O 0.77709(12) -0.08300(14) 0.32190(12) 0.0336(4) Uani 1 1 d . . .
H2 H 0.7822 -0.0841 0.2559 0.050 Uiso 1 1 calc R . .
O3 O 0.88598(10) 0.23167(13) 0.48658(12) 0.0283(4) Uani 1 1 d . . .
O4 O 1.19451(11) 0.40196(14) 0.38728(12) 0.0323(4) Uani 1 1 d . . .
H1N H 1.1964(17) 0.234(2) 0.582(2) 0.038(7) 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 O1 1.423(3) . ?
C2 O1 1.374(3) . ?
C2 C7 1.385(3) . ?
C2 C3 1.392(3) . ?
C3 C4 1.399(3) . ?
C4 C5 1.378(3) . ?
C5 C6 1.383(3) . ?
C5 C8 1.525(3) . ?
C6 C7 1.384(3) . ?
C8 O2 1.429(3) . ?
C8 C9 1.526(3) . ?
C9 C10 1.389(3) . ?
C9 C14 1.398(3) . ?
C10 C11 1.384(3) . ?
C11 C12 1.384(3) . ?
C12 C13 1.389(3) . ?
C13 C14 1.396(3) . ?
C13 C16 1.517(3) . ?
C14 O3 1.387(2) . ?
C15 O3 1.437(3) . ?
C16 N1 1.455(3) . ?
C17 O4 1.236(3) . ?
C17 N1 1.337(3) . ?
C17 C18 1.536(3) . ?
C18 C20 1.529(3) . ?
C18 C21 1.531(3) . ?
C18 C19 1.534(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 C7 116.0(2) . . ?
O1 C2 C3 124.5(2) . . ?
C7 C2 C3 119.5(2) . . ?
C2 C3 C4 118.8(2) . . ?
C5 C4 C3 122.0(2) . . ?
C4 C5 C6 118.2(2) . . ?
C4 C5 C8 120.88(19) . . ?
C6 C5 C8 120.89(19) . . ?
C5 C6 C7 121.0(2) . . ?
C6 C7 C2 120.5(2) . . ?
O2 C8 C5 109.94(17) . . ?
O2 C8 C9 112.76(17) . . ?
C5 C8 C9 113.67(17) . . ?
C10 C9 C14 118.3(2) . . ?
C10 C9 C8 122.6(2) . . ?
C14 C9 C8 119.09(19) . . ?
C11 C10 C9 120.1(2) . . ?
C12 C11 C10 121.1(2) . . ?
C11 C12 C13 120.4(2) . . ?
C12 C13 C14 118.0(2) . . ?
C12 C13 C16 123.1(2) . . ?
C14 C13 C16 118.82(19) . . ?
O3 C14 C13 119.03(19) . . ?
O3 C14 C9 118.59(19) . . ?
C13 C14 C9 122.22(19) . . ?
N1 C16 C13 114.88(18) . . ?
O4 C17 N1 120.4(2) . . ?
O4 C17 C18 122.21(19) . . ?
N1 C17 C18 117.35(19) . . ?
C20 C18 C21 109.5(2) . . ?
C20 C18 C19 110.18(19) . . ?
C21 C18 C19 109.3(2) . . ?
C20 C18 C17 111.82(19) . . ?
C21 C18 C17 108.53(18) . . ?
C19 C18 C17 107.45(18) . . ?
C17 N1 C16 121.11(19) . . ?
C2 O1 C1 117.66(19) . . ?
C14 O3 C15 115.03(16) . . ?
 
_diffrn_measured_fraction_theta_max    0.966
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.966
_refine_diff_density_max    0.289
_refine_diff_density_min   -0.196
_refine_diff_density_rms    0.048
