 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C22 H28 N2 O2'
_chemical_formula_weight          352.46
 
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   0.0000
 '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   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Orthorhombic
_symmetry_space_group_name_H-M    Pca2(1)
_symmetry_space_group_name_hall   'P 2c -2ac'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 'x+1/2, -y, z'
 '-x+1/2, y, z+1/2'
 
_cell_length_a                    17.1687(3)
_cell_length_b                    6.09270(10)
_cell_length_c                    18.4778(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1932.85(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     11139
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.28
_exptl_crystal_size_mid           0.12
_exptl_crystal_size_min           0.08
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.211
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              760
_exptl_absorpt_coefficient_mu     0.078
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9786
_exptl_absorpt_correction_T_max   0.9938
_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          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Nonius KappaCCD'
_diffrn_measurement_method        'φ & ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_decay_%         negligible
_diffrn_reflns_number             20822
_diffrn_reflns_av_R_equivalents   0.0535
_diffrn_reflns_av_sigmaI/netI     0.0254
_diffrn_reflns_limit_h_min        -21
_diffrn_reflns_limit_h_max        22
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          3.24
_diffrn_reflns_theta_max          27.49
_reflns_number_total              2272
_reflns_number_gt                 1807
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     ?
_computing_publication_material   SHELXL-97
 
_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)+(0.0628P)²+0.2050P] 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        0.025(5)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          2272
_refine_ls_number_parameters      238
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0559
_refine_ls_R_factor_gt            0.0407
_refine_ls_wR_factor_ref          0.1156
_refine_ls_wR_factor_gt           0.1057
_refine_ls_goodness_of_fit_ref    1.037
_refine_ls_restrained_S_all       1.037
_refine_ls_shift/su_max           0.006
_refine_ls_shift/su_mean          0.001
 
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 0.15067(13) 0.8315(5) 0.06414(14) 0.0511(6) Uani 1 1 d . . .
C2 C 0.16226(19) 1.0335(6) 0.0956(2) 0.0640(8) Uani 1 1 d . . .
H2 H 0.1981 1.1338 0.0745 0.077 Uiso 1 1 calc R . .
C3 C 0.1219(2) 1.0922(8) 0.1581(2) 0.0877(12) Uani 1 1 d . . .
H3 H 0.1300 1.2322 0.1796 0.105 Uiso 1 1 calc R . .
C4 C 0.0703(2) 0.9461(10) 0.1886(2) 0.0994(16) Uani 1 1 d . . .
H4 H 0.0439 0.9830 0.2322 0.119 Uiso 1 1 calc R . .
C5 C 0.0572(2) 0.7507(9) 0.1567(2) 0.0921(13) Uani 1 1 d . . .
H5 H 0.0202 0.6524 0.1769 0.110 Uiso 1 1 calc R . .
C6 C 0.09721(17) 0.6924(6) 0.09490(18) 0.0679(8) Uani 1 1 d . . .
H6 H 0.0876 0.5536 0.0732 0.081 Uiso 1 1 calc R . .
C7 C 0.19526(15) 0.7708(6) -0.00285(16) 0.0608(7) Uani 1 1 d . . .
H7A H 0.1776 0.6256 -0.0204 0.073 Uiso 1 1 calc R . .
H7B H 0.1847 0.8800 -0.0413 0.073 Uiso 1 1 calc R . .
C8 C 0.29893(15) 0.5676(5) 0.05492(15) 0.0557(7) Uani 1 1 d . . .
H8A H 0.2872 0.4340 0.0264 0.067 Uiso 1 1 calc R . .
H8B H 0.2663 0.5651 0.0991 0.067 Uiso 1 1 calc R . .
C9 C 0.38296(15) 0.5680(6) 0.07575(15) 0.0582(7) Uani 1 1 d . . .
H9A H 0.3934 0.6935 0.1084 0.070 Uiso 1 1 calc R . .
H9B H 0.3953 0.4312 0.1023 0.070 Uiso 1 1 calc R . .
C10 C 0.41545(13) 0.7755(4) -0.03014(12) 0.0402(5) Uani 1 1 d . . .
C11 C 0.43556(17) 0.9832(5) 0.0116(2) 0.0586(8) Uani 1 1 d . . .
H11A H 0.3919 1.0229 0.0431 0.088 Uiso 1 1 calc R . .
H11B H 0.4456 1.1030 -0.0225 0.088 Uiso 1 1 calc R . .
H11C H 0.4821 0.9574 0.0411 0.088 Uiso 1 1 calc R . .
C12 C 0.32795(13) 0.7792(4) -0.05324(13) 0.0413(5) Uani 1 1 d . . .
C13 C 0.31039(16) 0.9889(4) -0.0958(2) 0.0566(8) Uani 1 1 d . . .
H13A H 0.3546 1.0237 -0.1273 0.085 Uiso 1 1 calc R . .
H13B H 0.3017 1.1105 -0.0620 0.085 Uiso 1 1 calc R . .
H13C H 0.2636 0.9669 -0.1254 0.085 Uiso 1 1 calc R . .
C14 C 0.35816(15) 0.5703(5) -0.15905(14) 0.0560(6) Uani 1 1 d . . .
H14A H 0.3491 0.6974 -0.1914 0.067 Uiso 1 1 calc R . .
H14B H 0.3443 0.4352 -0.1859 0.067 Uiso 1 1 calc R . .
C15 C 0.44277(14) 0.5622(5) -0.13775(15) 0.0513(6) Uani 1 1 d . . .
H15A H 0.4528 0.4276 -0.1092 0.062 Uiso 1 1 calc R . .
H15B H 0.4756 0.5568 -0.1818 0.062 Uiso 1 1 calc R . .
C16 C 0.54819(14) 0.7548(5) -0.08094(14) 0.0559(7) Uani 1 1 d . . .
H16A H 0.5647 0.6061 -0.0658 0.067 Uiso 1 1 calc R . .
H16B H 0.5602 0.8578 -0.0410 0.067 Uiso 1 1 calc R . .
C17 C 0.59274(13) 0.8215(5) -0.14749(14) 0.0492(6) Uani 1 1 d . . .
C18 C 0.58320(18) 1.0283(6) -0.17687(19) 0.0594(7) Uani 1 1 d . . .
H18 H 0.5486 1.1287 -0.1542 0.071 Uiso 1 1 calc R . .
C19 C 0.62265(18) 1.0923(6) -0.23821(18) 0.0705(8) Uani 1 1 d . . .
H19 H 0.6154 1.2359 -0.2571 0.085 Uiso 1 1 calc R . .
C20 C 0.6722(2) 0.9495(7) -0.2720(2) 0.0756(10) Uani 1 1 d . . .
H20 H 0.6988 0.9927 -0.3148 0.091 Uiso 1 1 calc R . .
C21 C 0.68325(18) 0.7437(6) -0.24376(19) 0.0741(9) Uani 1 1 d . . .
H21 H 0.7177 0.6444 -0.2671 0.089 Uiso 1 1 calc R . .
C22 C 0.64430(16) 0.6788(5) -0.18101(16) 0.0617(7) Uani 1 1 d . . .
H22 H 0.6531 0.5370 -0.1613 0.074 Uiso 1 1 calc R . .
N1 N 0.28007(11) 0.7629(3) 0.01194(11) 0.0454(5) Uani 1 1 d . . .
N2 N 0.46347(11) 0.7551(3) -0.09479(11) 0.0437(4) Uani 1 1 d . . .
O1 O 0.43141(9) 0.5842(3) 0.01339(9) 0.0499(4) Uani 1 1 d . . .
O2 O 0.31018(9) 0.5893(3) -0.09677(9) 0.0512(4) Uani 1 1 d . . .
 
 
_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 C6 1.372(4) . ?
C1 C2 1.376(4) . ?
C1 C7 1.502(4) . ?
C2 C3 1.394(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.348(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.482(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N1 1.467(4) . ?
C8 C9 1.493(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O1 1.424(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O1 1.443(3) . ?
C10 N2 1.457(3) . ?
C10 C11 1.522(4) . ?
C10 C12 1.562(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O2 1.442(3) . ?
C12 N1 1.461(3) . ?
C12 C13 1.531(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 O2 1.420(3) . ?
C14 C15 1.506(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 N2 1.462(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N2 1.477(3) . ?
C16 C17 1.504(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.382(4) . ?
C17 C22 1.387(4) . ?
C18 C19 1.377(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.368(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.372(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.395(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
 
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
C6 C1 C2 118.3(3) . . ?
C6 C1 C7 122.0(3) . . ?
C2 C1 C7 119.7(3) . . ?
C1 C2 C3 120.5(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 121.1(4) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
N1 C7 C1 110.9(2) . . ?
N1 C7 H7A 109.5 . . ?
C1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 C9 110.6(2) . . ?
N1 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
O1 C9 C8 110.8(2) . . ?
O1 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
O1 C10 N2 106.30(17) . . ?
O1 C10 C11 110.3(2) . . ?
N2 C10 C11 111.0(2) . . ?
O1 C10 C12 110.28(19) . . ?
N2 C10 C12 108.75(15) . . ?
C11 C10 C12 110.2(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 N1 106.64(18) . . ?
O2 C12 C13 110.0(2) . . ?
N1 C12 C13 111.7(2) . . ?
O2 C12 C10 110.15(19) . . ?
N1 C12 C10 108.35(16) . . ?
C13 C12 C10 110.0(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 C15 110.5(2) . . ?
O2 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N2 C15 C14 110.5(2) . . ?
N2 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N2 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N2 C16 C17 111.03(19) . . ?
N2 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N2 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C18 C17 C22 118.1(3) . . ?
C18 C17 C16 120.5(3) . . ?
C22 C17 C16 121.4(3) . . ?
C19 C18 C17 121.6(3) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C20 C19 C18 120.1(4) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 119.6(3) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C20 C21 C22 120.6(3) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C17 C22 C21 120.0(3) . . ?
C17 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C12 N1 C8 112.16(18) . . ?
C12 N1 C7 113.47(19) . . ?
C8 N1 C7 110.0(2) . . ?
C10 N2 C15 112.11(18) . . ?
C10 N2 C16 114.54(19) . . ?
C15 N2 C16 109.4(2) . . ?
C9 O1 C10 113.33(18) . . ?
C14 O2 C12 113.25(18) . . ?
 
_diffrn_measured_fraction_theta_max    0.993
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.993
_refine_diff_density_max    0.159
_refine_diff_density_min   -0.128
_refine_diff_density_rms    0.028
