 
data_02src630
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C16 H36 N2 O2'
_chemical_formula_sum
 'C16 H36 N2 O2'
_chemical_formula_weight          288.47
 
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  -C2yc
 
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                    25.225(2)
_cell_length_b                    6.2785(7)
_cell_length_c                    10.9206(11)
_cell_angle_alpha                 90.00
_cell_angle_beta                  94.662(7)
_cell_angle_gamma                 90.00
_cell_volume                      1723.8(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     4526
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.10
_exptl_crystal_size_mid           0.03
_exptl_crystal_size_min           0.03
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.112
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              648
_exptl_absorpt_coefficient_mu     0.072
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9928
_exptl_absorpt_correction_T_max   0.9978
_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_reflns_number             5130
_diffrn_reflns_av_R_equivalents   0.0538
_diffrn_reflns_av_sigmaI/netI     0.0531
_diffrn_reflns_limit_h_min        -25
_diffrn_reflns_limit_h_max        27
_diffrn_reflns_limit_k_min        -6
_diffrn_reflns_limit_k_max        6
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          3.24
_diffrn_reflns_theta_max          23.25
_reflns_number_total              1223
_reflns_number_gt                 700
_reflns_threshold_expression      >2σ(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 > 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)+(0.1700P)²+10.1802P] 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      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          1223
_refine_ls_number_parameters      95
_refine_ls_number_restraints      60
_refine_ls_R_factor_all           0.1942
_refine_ls_R_factor_gt            0.1386
_refine_ls_wR_factor_ref          0.4144
_refine_ls_wR_factor_gt           0.3676
_refine_ls_goodness_of_fit_ref    1.103
_refine_ls_restrained_S_all       1.117
_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
N1 N 0.9672(3) 0.1184(17) 0.0777(8) 0.127(4) Uani 1 1 d U . .
H1N H 0.9929 0.1742 0.1347 0.153 Uiso 1 1 calc R . .
O1 O 0.9378(2) 0.3545(11) 0.2886(5) 0.099(2) Uani 1 1 d U . .
H1 H 0.9631 0.2687 0.3016 0.148 Uiso 1 1 calc R . .
C1 C 0.8032(3) 0.268(2) 0.1206(9) 0.122(4) Uani 1 1 d U . .
H1A H 0.7676 0.3039 0.1442 0.184 Uiso 1 1 calc R . .
H1B H 0.8058 0.1135 0.1096 0.184 Uiso 1 1 calc R . .
H1C H 0.8093 0.3398 0.0433 0.184 Uiso 1 1 calc R . .
C2 C 0.8309(3) 0.2457(15) 0.3426(8) 0.085(3) Uani 1 1 d U . .
H2A H 0.8569 0.2933 0.4085 0.127 Uiso 1 1 calc R . .
H2B H 0.8316 0.0899 0.3374 0.127 Uiso 1 1 calc R . .
H2C H 0.7952 0.2928 0.3602 0.127 Uiso 1 1 calc R . .
C3 C 0.8427(3) 0.5794(16) 0.2297(8) 0.093(3) Uani 1 1 d U . .
H3A H 0.8074 0.6233 0.2516 0.140 Uiso 1 1 calc R . .
H3B H 0.8496 0.6418 0.1503 0.140 Uiso 1 1 calc R . .
H3C H 0.8697 0.6288 0.2929 0.140 Uiso 1 1 calc R . .
C4 C 0.8448(3) 0.3405(14) 0.2211(6) 0.071(2) Uani 1 1 d U . .
C5 C 0.9010(3) 0.273(2) 0.1944(10) 0.141(5) Uani 1 1 d U . .
H5 H 0.8982 0.1316 0.2357 0.170 Uiso 1 1 calc R . .
C6 C 0.9146(4) 0.197(3) 0.1034(15) 0.227(10) Uani 1 1 d U . .
H6A H 0.9053 0.3044 0.0388 0.273 Uiso 1 1 calc R . .
H6B H 0.8902 0.0757 0.0854 0.273 Uiso 1 1 calc R . .
C7 C 0.9704(4) -0.113(2) 0.0788(9) 0.125(4) Uani 1 1 d U . .
H7A H 0.9419 -0.1715 0.0206 0.150 Uiso 1 1 calc R . .
H7B H 0.9643 -0.1658 0.1619 0.150 Uiso 1 1 calc R . .
C8 C 1.0233(4) -0.1924(19) 0.0440(9) 0.124(5) Uani 1 1 d U . .
H8A H 1.0519 -0.1400 0.1040 0.149 Uiso 1 1 calc R . .
H8B H 1.0239 -0.3500 0.0457 0.149 Uiso 1 1 calc R . .
 
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
N1 0.067(5) 0.204(10) 0.105(6) -0.108(7) -0.028(4) 0.062(5)
O1 0.052(3) 0.152(6) 0.092(4) -0.044(4) 0.002(3) 0.003(3)
C1 0.059(5) 0.218(12) 0.090(6) -0.062(7) 0.001(4) -0.002(6)
C2 0.059(5) 0.107(7) 0.090(6) -0.001(5) 0.009(4) 0.005(4)
C3 0.062(5) 0.134(9) 0.085(6) 0.014(5) 0.007(4) -0.002(5)
C4 0.050(4) 0.104(7) 0.059(4) -0.026(4) 0.011(3) -0.001(4)
C5 0.047(5) 0.266(14) 0.112(7) -0.118(9) 0.013(5) 0.001(6)
C6 0.072(7) 0.41(2) 0.189(13) -0.201(15) -0.027(8) 0.085(10)
C7 0.086(7) 0.207(12) 0.079(6) -0.075(7) -0.014(5) 0.040(7)
C8 0.108(7) 0.167(10) 0.089(7) -0.078(7) -0.047(5) 0.063(7)
 
_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
N1 C8 1.445(15) 5_755 ?
N1 C7 1.455(14) . ?
N1 C6 1.465(12) . ?
N1 H1N 0.9300 . ?
O1 C5 1.423(10) . ?
O1 H1 0.8400 . ?
C1 C4 1.526(10) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C4 1.521(11) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.504(12) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.531(11) . ?
C5 C6 1.177(13) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.503(13) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N1 1.445(15) 5_755 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
 
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
C8 N1 C7 108.4(7) 5_755 . ?
C8 N1 C6 106.7(11) 5_755 . ?
C7 N1 C6 112.7(12) . . ?
C8 N1 H1N 109.7 5_755 . ?
C7 N1 H1N 109.7 . . ?
C6 N1 H1N 109.7 . . ?
C5 O1 H1 109.5 . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C3 C4 C2 108.9(7) . . ?
C3 C4 C1 108.5(8) . . ?
C2 C4 C1 108.5(7) . . ?
C3 C4 C5 109.1(8) . . ?
C2 C4 C5 109.9(8) . . ?
C1 C4 C5 112.0(6) . . ?
C6 C5 O1 122.5(9) . . ?
C6 C5 C4 127.6(9) . . ?
O1 C5 C4 108.8(6) . . ?
C6 C5 H5 93.4 . . ?
O1 C5 H5 93.4 . . ?
C4 C5 H5 93.4 . . ?
C5 C6 N1 129.0(11) . . ?
C5 C6 H6A 105.0 . . ?
N1 C6 H6A 105.0 . . ?
C5 C6 H6B 105.0 . . ?
N1 C6 H6B 105.0 . . ?
H6A C6 H6B 105.9 . . ?
N1 C7 C8 112.2(11) . . ?
N1 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 C7 110.0(8) 5_755 . ?
N1 C8 H8A 109.7 5_755 . ?
C7 C8 H8A 109.7 . . ?
N1 C8 H8B 109.7 5_755 . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              23.25
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.485
_refine_diff_density_min   -0.399
_refine_diff_density_rms    0.072
