data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety         'C24 H23 N O3'
_chemical_formula_sum
 'C24 H23 N O3'
_chemical_formula_weight          373.43
 
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)/n
_symmetry_space_group_name_hall   -P2yn
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    16.5792(12)
_cell_length_b                    5.8605(5)
_cell_length_c                    21.980(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  111.754(3)
_cell_angle_gamma                 90.00
_cell_volume                      1983.5(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     24493
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.05
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.251
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              792
_exptl_absorpt_coefficient_mu     0.082
_exptl_absorpt_correction_type    Multi-scan
_exptl_absorpt_correction_T_min   0.9758
_exptl_absorpt_correction_T_max   0.9959
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_exptl_special_details
;
?
;
 
_diffrn_ambient_temperature       120(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   'Bruker Nonius Kappa CCD Area detector'
_diffrn_measurement_method        'φ and ω scans to fill the asymmetric unit'
_diffrn_detector_area_resol_mean  '9.091 pixels mm^1^'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             6370
_diffrn_reflns_av_R_equivalents   0.1060
_diffrn_reflns_av_sigmaI/netI     0.1430
_diffrn_reflns_limit_h_min        -19
_diffrn_reflns_limit_h_max        19
_diffrn_reflns_limit_k_min        -6
_diffrn_reflns_limit_k_max        6
_diffrn_reflns_limit_l_min        -26
_diffrn_reflns_limit_l_max        25
_diffrn_reflns_theta_min          3.62
_diffrn_reflns_theta_max          25.03
_reflns_number_total              3474
_reflns_number_gt                 1945
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'COLLECT (Hooft, 1998)'
_computing_cell_refinement        'DENZO (Otwinowski and MInor, 1997)'
_computing_data_reduction         'DENZO, COLLECT, MAXUS (Mackay et al., 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'CAMERON (Watkin, et al., 1993)'
_computing_publication_material   'WINGX (Farrugia, 1998)'
 
_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)+(0.0377P)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     constr
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.0136(17)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3474
_refine_ls_number_parameters      255
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1342
_refine_ls_R_factor_gt            0.0651
_refine_ls_wR_factor_ref          0.1410
_refine_ls_wR_factor_gt           0.1196
_refine_ls_goodness_of_fit_ref    0.986
_refine_ls_restrained_S_all       0.986
_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 1.04986(18) -0.3481(5) 0.18809(14) 0.0256(7) Uani 1 1 d . . .
C2 C 1.03485(19) -0.5414(5) 0.14851(15) 0.0306(8) Uani 1 1 d . . .
H2 H 0.9793 -0.6120 0.1334 0.037 Uiso 1 1 calc R . .
C3 C 1.1006(2) -0.6314(5) 0.13099(16) 0.0361(8) Uani 1 1 d . . .
H3 H 1.0898 -0.7652 0.1048 0.043 Uiso 1 1 calc R . .
C4 C 1.1811(2) -0.5303(6) 0.15083(16) 0.0373(9) Uani 1 1 d . . .
H4 H 1.2256 -0.5921 0.1383 0.045 Uiso 1 1 calc R . .
C5 C 1.19587(18) -0.3360(5) 0.18955(16) 0.0335(8) Uani 1 1 d . . .
H5 H 1.2511 -0.2641 0.2034 0.040 Uiso 1 1 calc R . .
C6 C 1.13191(17) -0.2458(5) 0.20818(15) 0.0297(8) Uani 1 1 d . . .
H6 H 1.1435 -0.1131 0.2349 0.036 Uiso 1 1 calc R . .
C7 C 0.99137(17) -0.0248(5) 0.23202(15) 0.0280(8) Uani 1 1 d . . .
H7 H 1.0149 0.0730 0.2051 0.034 Uiso 1 1 calc R . .
C8 C 1.04752(17) 0.0057(5) 0.30398(15) 0.0258(7) Uani 1 1 d . . .
C9 C 1.08870(17) 0.2130(5) 0.32375(16) 0.0302(8) Uani 1 1 d . . .
H9 H 1.0831 0.3290 0.2922 0.036 Uiso 1 1 calc R . .
C10 C 1.13818(18) 0.2532(5) 0.38926(17) 0.0367(9) Uani 1 1 d . . .
H10 H 1.1667 0.3957 0.4023 0.044 Uiso 1 1 calc R . .
C11 C 1.14604(19) 0.0864(6) 0.43554(17) 0.0392(9) Uani 1 1 d . . .
H11 H 1.1798 0.1139 0.4804 0.047 Uiso 1 1 calc R . .
C12 C 1.10456(19) -0.1207(6) 0.41617(16) 0.0369(8) Uani 1 1 d . . .
H12 H 1.1095 -0.2353 0.4479 0.044 Uiso 1 1 calc R . .
C13 C 1.05570(18) -0.1621(5) 0.35050(16) 0.0323(8) Uani 1 1 d . . .
H13 H 1.0279 -0.3055 0.3374 0.039 Uiso 1 1 calc R . .
C14 C 0.85239(17) -0.1630(5) 0.21139(15) 0.0302(8) Uani 1 1 d . . .
H14 H 0.8582 -0.2230 0.2554 0.036 Uiso 1 1 calc R . .
C15 C 0.75825(17) -0.1120(5) 0.17225(15) 0.0275(8) Uani 1 1 d . . .
C16 C 0.73237(18) 0.0796(5) 0.13350(16) 0.0336(8) Uani 1 1 d . . .
H16 H 0.7743 0.1889 0.1328 0.040 Uiso 1 1 calc R . .
C17 C 0.64506(19) 0.1138(6) 0.09534(16) 0.0390(9) Uani 1 1 d . . .
H17 H 0.6276 0.2473 0.0692 0.047 Uiso 1 1 calc R . .
C18 C 0.5841(2) -0.0454(6) 0.09541(17) 0.0400(9) Uani 1 1 d . . .
H18 H 0.5246 -0.0230 0.0689 0.048 Uiso 1 1 calc R . .
C19 C 0.6093(2) -0.2370(6) 0.13390(18) 0.0440(10) Uani 1 1 d . . .
H19 H 0.5672 -0.3468 0.1341 0.053 Uiso 1 1 calc R . .
C20 C 0.69601(19) -0.2703(6) 0.17243(17) 0.0395(9) Uani 1 1 d . . .
H20 H 0.7130 -0.4025 0.1992 0.047 Uiso 1 1 calc R . .
C21 C 0.89541(16) -0.3311(5) 0.17884(14) 0.0248(7) Uani 1 1 d . . .
H21 H 0.8887 -0.4906 0.1924 0.030 Uiso 1 1 calc R . .
C22 C 0.85596(19) -0.3120(5) 0.10462(16) 0.0295(8) Uani 1 1 d . . .
C23 C 0.8445(2) -0.0975(6) 0.01156(16) 0.0391(9) Uani 1 1 d . . .
H23A H 0.7805 -0.0873 -0.0026 0.047 Uiso 1 1 calc R . .
H23B H 0.8588 -0.2282 -0.0111 0.047 Uiso 1 1 calc R . .
C24 C 0.8804(2) 0.1201(5) -0.00466(17) 0.0424(9) Uani 1 1 d . . .
H24A H 0.8642 0.2487 0.0169 0.064 Uiso 1 1 calc R . .
H24B H 0.8565 0.1437 -0.0522 0.064 Uiso 1 1 calc R . .
H24C H 0.9438 0.1096 0.0107 0.064 Uiso 1 1 calc R . .
N1 N 0.98555(14) -0.2613(4) 0.20881(12) 0.0261(6) Uani 1 1 d . . .
O1 O 0.90377(11) 0.0404(3) 0.21961(10) 0.0310(6) Uani 1 1 d . . .
O2 O 0.80332(13) -0.4457(4) 0.07076(11) 0.0391(6) Uani 1 1 d . . .
O3 O 0.88392(11) -0.1282(3) 0.08244(10) 0.0307(5) Uani 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 C2 1.394(4) . ?
C1 C6 1.400(4) . ?
C1 N1 1.401(4) . ?
C2 C3 1.387(4) . ?
C3 C4 1.375(4) . ?
C4 C5 1.388(4) . ?
C5 C6 1.376(4) . ?
C7 O1 1.427(3) . ?
C7 N1 1.468(4) . ?
C7 C8 1.519(4) . ?
C8 C9 1.383(4) . ?
C8 C13 1.389(4) . ?
C9 C10 1.388(4) . ?
C10 C11 1.382(5) . ?
C11 C12 1.382(4) . ?
C12 C13 1.390(4) . ?
C14 O1 1.437(3) . ?
C14 C15 1.507(4) . ?
C14 C21 1.539(4) . ?
C15 C16 1.378(4) . ?
C15 C20 1.389(4) . ?
C16 C17 1.393(4) . ?
C17 C18 1.377(4) . ?
C18 C19 1.374(4) . ?
C19 C20 1.386(4) . ?
C21 N1 1.451(3) . ?
C21 C22 1.520(4) . ?
C22 O2 1.203(3) . ?
C22 O3 1.335(3) . ?
C23 O3 1.460(4) . ?
C23 C24 1.505(4) . ?
 
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
C2 C1 C6 118.2(3) . . ?
C2 C1 N1 121.1(3) . . ?
C6 C1 N1 120.6(3) . . ?
C3 C2 C1 120.4(3) . . ?
C4 C3 C2 121.2(3) . . ?
C3 C4 C5 118.6(3) . . ?
C6 C5 C4 121.1(3) . . ?
C5 C6 C1 120.5(3) . . ?
O1 C7 N1 104.8(2) . . ?
O1 C7 C8 110.8(2) . . ?
N1 C7 C8 114.1(2) . . ?
C9 C8 C13 119.3(3) . . ?
C9 C8 C7 118.1(3) . . ?
C13 C8 C7 122.6(3) . . ?
C8 C9 C10 120.6(3) . . ?
C11 C10 C9 120.1(3) . . ?
C10 C11 C12 119.6(3) . . ?
C11 C12 C13 120.4(3) . . ?
C8 C13 C12 120.1(3) . . ?
O1 C14 C15 110.3(2) . . ?
O1 C14 C21 103.5(2) . . ?
C15 C14 C21 115.0(2) . . ?
C16 C15 C20 119.0(3) . . ?
C16 C15 C14 122.3(3) . . ?
C20 C15 C14 118.7(3) . . ?
C15 C16 C17 120.4(3) . . ?
C18 C17 C16 120.1(3) . . ?
C19 C18 C17 119.9(3) . . ?
C18 C19 C20 120.1(3) . . ?
C19 C20 C15 120.5(3) . . ?
N1 C21 C22 115.3(2) . . ?
N1 C21 C14 100.7(2) . . ?
C22 C21 C14 111.3(2) . . ?
O2 C22 O3 124.8(3) . . ?
O2 C22 C21 122.8(3) . . ?
O3 C22 C21 112.4(3) . . ?
O3 C23 C24 107.3(2) . . ?
C1 N1 C21 122.0(2) . . ?
C1 N1 C7 119.7(2) . . ?
C21 N1 C7 110.4(2) . . ?
C7 O1 C14 108.4(2) . . ?
C22 O3 C23 114.2(2) . . ?
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              25.03
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.220
_refine_diff_density_min   -0.211
_refine_diff_density_rms    0.051
