 
data_2008src1307p21c
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C15 H24 N2 O2'
_chemical_formula_weight          264.36
 
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    P21/c
 
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                    14.4770(5)
_cell_length_b                    11.2719(4)
_cell_length_c                    9.0254(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  102.352(2)
_cell_angle_gamma                 90.00
_cell_volume                      1438.70(9)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     12305
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.16
_exptl_crystal_size_mid           0.07
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.220
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              576
_exptl_absorpt_coefficient_mu     0.081
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9871
_exptl_absorpt_correction_T_max   0.9992
_exptl_absorpt_process_details    'SADABS 2007/2 (Sheldrick, G.M., 2007)'
 
_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 APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '4096x4096pixels / 62x62mm'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             15666
_diffrn_reflns_av_R_equivalents   0.1104
_diffrn_reflns_av_sigmaI/netI     0.0993
_diffrn_reflns_limit_h_min        -18
_diffrn_reflns_limit_h_max        18
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          3.40
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3269
_reflns_number_gt                 2051
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_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 > 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)+(0.0000P)²+2.3107P] 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_number_reflns          3269
_refine_ls_number_parameters      177
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1550
_refine_ls_R_factor_gt            0.0838
_refine_ls_wR_factor_ref          0.1525
_refine_ls_wR_factor_gt           0.1255
_refine_ls_goodness_of_fit_ref    1.115
_refine_ls_restrained_S_all       1.115
_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
C2 C -0.22094(19) 0.0150(3) 0.9945(3) 0.0211(6) Uani 1 1 d . . .
H2A H -0.2152 0.0893 0.9387 0.025 Uiso 1 1 calc R . .
H2B H -0.2457 0.0360 1.0853 0.025 Uiso 1 1 calc R . .
C3 C -0.29226(19) -0.0669(2) 0.8926(3) 0.0181(6) Uani 1 1 d . . .
C4 C -0.39049(19) -0.0107(3) 0.8811(3) 0.0222(6) Uani 1 1 d . . .
H4A H -0.4029 -0.0023 0.9843 0.027 Uiso 1 1 calc R . .
H4B H -0.3907 0.0697 0.8369 0.027 Uiso 1 1 calc R . .
C5 C -0.4694(2) -0.0839(3) 0.7841(3) 0.0281(7) Uani 1 1 d . . .
H5A H -0.4584 -0.0919 0.6800 0.034 Uiso 1 1 calc R . .
H5B H -0.5310 -0.0438 0.7779 0.034 Uiso 1 1 calc R . .
C6 C -0.4713(2) -0.2068(3) 0.8558(4) 0.0329(8) Uani 1 1 d . . .
H6A H -0.4892 -0.1987 0.9552 0.039 Uiso 1 1 calc R . .
H6B H -0.5196 -0.2565 0.7898 0.039 Uiso 1 1 calc R . .
C7 C -0.3756(2) -0.2675(3) 0.8779(3) 0.0266(7) Uani 1 1 d . . .
H7A H -0.3630 -0.2880 0.7773 0.032 Uiso 1 1 calc R . .
H7B H -0.3774 -0.3423 0.9346 0.032 Uiso 1 1 calc R . .
C8 C -0.2947(2) -0.1901(3) 0.9636(3) 0.0217(6) Uani 1 1 d . . .
H8A H -0.2339 -0.2307 0.9653 0.026 Uiso 1 1 calc R . .
H8B H -0.3015 -0.1809 1.0698 0.026 Uiso 1 1 calc R . .
C10 C -0.2580(2) -0.0040(2) 0.6345(3) 0.0193(6) Uani 1 1 d . . .
C11 C -0.1912(2) -0.0242(3) 0.5457(3) 0.0226(6) Uani 1 1 d . . .
H11 H -0.1488 -0.0892 0.5692 0.027 Uiso 1 1 calc R . .
C12 C -0.1855(2) 0.0485(3) 0.4246(3) 0.0277(7) Uani 1 1 d . . .
H12 H -0.1395 0.0325 0.3662 0.033 Uiso 1 1 calc R . .
C13 C -0.2461(2) 0.1446(3) 0.3872(3) 0.0277(7) Uani 1 1 d . . .
H13 H -0.2430 0.1940 0.3031 0.033 Uiso 1 1 calc R . .
C14 C -0.3108(2) 0.1661(3) 0.4757(3) 0.0277(7) Uani 1 1 d . . .
H14 H -0.3518 0.2325 0.4532 0.033 Uiso 1 1 calc R . .
C15 C -0.3177(2) 0.0935(3) 0.5966(3) 0.0262(7) Uani 1 1 d . . .
H15 H -0.3637 0.1104 0.6545 0.031 Uiso 1 1 calc R . .
N1 N -0.12533(16) -0.0384(2) 1.0446(3) 0.0211(5) Uani 1 1 d . . .
H1A H -0.1280 -0.0985 1.1110 0.032 Uiso 1 1 calc R . .
H1B H -0.0840 0.0179 1.0909 0.032 Uiso 1 1 calc R . .
H1C H -0.1055 -0.0675 0.9626 0.032 Uiso 1 1 calc R . .
N9 N -0.26540(17) -0.0875(2) 0.7458(2) 0.0192(5) Uani 1 1 d . . .
H9 H -0.222(2) -0.144(3) 0.753(3) 0.023 Uiso 1 1 d . . .
C21 C -0.0535(2) 0.2884(3) 0.2501(3) 0.0293(7) Uani 1 1 d . . .
H21A H -0.0587 0.2653 0.3527 0.044 Uiso 1 1 calc R . .
H21B H -0.1113 0.2655 0.1777 0.044 Uiso 1 1 calc R . .
H21C H -0.0450 0.3745 0.2462 0.044 Uiso 1 1 calc R . .
C22 C 0.0303(2) 0.2269(3) 0.2098(3) 0.0206(6) Uani 1 1 d . . .
O23 O 0.01653(14) 0.12661(18) 0.1454(2) 0.0253(5) Uani 1 1 d . . .
O24 O 0.11002(14) 0.27643(18) 0.2435(2) 0.0239(5) 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
C2 N1 1.489(3) . ?
C2 C3 1.536(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N9 1.477(3) . ?
C3 C8 1.532(4) . ?
C3 C4 1.540(4) . ?
C4 C5 1.525(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.532(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.520(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.531(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C15 1.395(4) . ?
C10 N9 1.397(3) . ?
C10 C11 1.401(4) . ?
C11 C12 1.382(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.376(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N9 H9 0.89(3) . ?
C21 C22 1.508(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 O24 1.260(3) . ?
C22 O23 1.267(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
N1 C2 C3 113.6(2) . . ?
N1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
N1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
N9 C3 C8 105.5(2) . . ?
N9 C3 C2 111.1(2) . . ?
C8 C3 C2 111.5(2) . . ?
N9 C3 C4 114.9(2) . . ?
C8 C3 C4 107.3(2) . . ?
C2 C3 C4 106.6(2) . . ?
C5 C4 C3 112.6(2) . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C4 C5 C6 109.0(2) . . ?
C4 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
C4 C5 H5B 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C7 C6 C5 111.4(2) . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C8 112.8(3) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C3 112.9(2) . . ?
C7 C8 H8A 109.0 . . ?
C3 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C3 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C15 C10 N9 124.6(3) . . ?
C15 C10 C11 117.1(3) . . ?
N9 C10 C11 118.1(3) . . ?
C12 C11 C10 121.4(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 120.8(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 117.9(3) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C13 C14 C15 121.8(3) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C10 120.9(3) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C10 N9 C3 127.9(2) . . ?
C10 N9 H9 112.2(19) . . ?
C3 N9 H9 111.2(19) . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O24 C22 O23 123.5(3) . . ?
O24 C22 C21 118.7(3) . . ?
O23 C22 C21 117.7(3) . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
N1 H1A O24  0.91 1.91 2.807(3) 169.9 2_546
N1 H1B O23  0.91 1.89 2.776(3) 165.4 1_556
N9 H9 O24  0.89(3) 2.20(3) 3.084(3) 175(3) 3_556
N1 H1C O23  0.91 1.90 2.751(3) 155.8 3_556
 
_diffrn_measured_fraction_theta_max    0.989
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.989
_refine_diff_density_max    0.267
_refine_diff_density_min   -0.256
_refine_diff_density_rms    0.067
