 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C10 H24 N2, H2 O'
_chemical_formula_sum
 'C10 H26 N2 O'
_chemical_formula_weight          190.12
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0030   0.0020
 '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'   0.0060   0.0030
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0110   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Orthorhombic
_symmetry_space_group_name_H-M    Ccca
_symmetry_space_group_name_hall   '-C 2b 2bc'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y+1/2, z'
 'x, -y+1/2, -z+1/2'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, -y+1, z'
 'x+1/2, -y+1, -z+1/2'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, y-1/2, -z'
 '-x, y-1/2, z-1/2'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, y, -z'
 '-x+1/2, y, z-1/2'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    13.0370(5)
_cell_length_b                    19.1366(6)
_cell_length_c                    10.0187(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2499.50(16)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     10400
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.010
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              864
_exptl_absorpt_coefficient_mu     0.065
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9871
_exptl_absorpt_correction_T_max   0.9994
_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_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             14424
_diffrn_reflns_av_R_equivalents   0.1033
_diffrn_reflns_av_sigmaI/netI     0.0488
_diffrn_reflns_limit_h_min        -16
_diffrn_reflns_limit_h_max        16
_diffrn_reflns_limit_k_min        -24
_diffrn_reflns_limit_k_max        24
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          3.13
_diffrn_reflns_theta_max          27.43
_reflns_number_total              1421
_reflns_number_gt                 1022
_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)+(0.0435P)²+2.4571P] 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          1421
_refine_ls_number_parameters      63
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0907
_refine_ls_R_factor_gt            0.0561
_refine_ls_wR_factor_ref          0.1240
_refine_ls_wR_factor_gt           0.1115
_refine_ls_goodness_of_fit_ref    1.017
_refine_ls_restrained_S_all       1.017
_refine_ls_shift/su_max           0.001
_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 0.38167(9) 0.19452(6) 0.01963(12) 0.0157(3) Uani 1 1 d . . .
H1N H 0.3539 0.2156 -0.0477 0.019 Uiso 1 1 d R . .
C1 C 0.35465(11) 0.11906(7) 0.00668(15) 0.0146(3) Uani 1 1 d . . .
C2 C 0.39761(13) 0.08616(9) -0.12116(16) 0.0246(4) Uani 1 1 d . . .
H2A H 0.3762 0.1140 -0.1985 0.037 Uiso 1 1 calc R . .
H2B H 0.3714 0.0384 -0.1303 0.037 Uiso 1 1 calc R . .
H2C H 0.4727 0.0851 -0.1165 0.037 Uiso 1 1 calc R . .
C3 C 0.23778(11) 0.11623(8) 0.00350(17) 0.0207(4) Uani 1 1 d . . .
H3A H 0.2103 0.1358 0.0865 0.031 Uiso 1 1 calc R . .
H3B H 0.2154 0.0676 -0.0056 0.031 Uiso 1 1 calc R . .
H3C H 0.2125 0.1435 -0.0725 0.031 Uiso 1 1 calc R . .
C4 C 0.39480(13) 0.07944(8) 0.12844(16) 0.0231(4) Uani 1 1 d . . .
H4A H 0.4699 0.0786 0.1263 0.035 Uiso 1 1 calc R . .
H4B H 0.3685 0.0315 0.1270 0.035 Uiso 1 1 calc R . .
H4C H 0.3717 0.1029 0.2100 0.035 Uiso 1 1 calc R . .
C5 C 0.49205(12) 0.21073(8) 0.01947(17) 0.0217(4) Uani 1 1 d . . .
H5A H 0.5246 0.1901 -0.0606 0.026 Uiso 1 1 calc R . .
H5B H 0.5248 0.1901 0.0994 0.026 Uiso 1 1 calc R . .
O1 O 0.26427(11) 0.2500 0.2500 0.0237(4) Uani 1 2 d S . .
H3O H 0.3037 0.2333 0.1798 0.036 Uiso 1 1 d 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 0.0123(6) 0.0149(6) 0.0198(7) 0.0010(5) -0.0020(5) -0.0015(5)
C1 0.0155(7) 0.0140(7) 0.0144(7) -0.0014(6) -0.0005(6) -0.0023(6)
C2 0.0294(9) 0.0241(9) 0.0203(8) -0.0058(7) 0.0022(7) -0.0023(7)
C3 0.0162(7) 0.0206(8) 0.0254(8) 0.0019(7) -0.0028(7) -0.0039(6)
C4 0.0290(9) 0.0203(9) 0.0201(8) 0.0033(7) -0.0063(7) -0.0005(7)
C5 0.0141(8) 0.0175(8) 0.0336(9) 0.0007(7) -0.0005(7) -0.0012(6)
O1 0.0217(8) 0.0272(9) 0.0222(8) -0.0044(7) 0.000 0.000
 
_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 C5 1.4721(19) . ?
N1 C1 1.4919(17) . ?
N1 H1N 0.8652 . ?
C1 C3 1.525(2) . ?
C1 C4 1.529(2) . ?
C1 C2 1.533(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C5 1.517(3) 2_655 ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
O1 H3O 0.9283 . ?
 
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
C5 N1 C1 115.77(11) . . ?
C5 N1 H1N 108.0 . . ?
C1 N1 H1N 106.6 . . ?
N1 C1 C3 105.79(11) . . ?
N1 C1 C4 109.26(12) . . ?
C3 C1 C4 109.95(13) . . ?
N1 C1 C2 112.57(13) . . ?
C3 C1 C2 109.45(13) . . ?
C4 C1 C2 109.75(13) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C5 110.02(16) . 2_655 ?
N1 C5 H5A 109.7 . . ?
C5 C5 H5A 109.7 2_655 . ?
N1 C5 H5B 109.7 . . ?
C5 C5 H5B 109.7 2_655 . ?
H5A C5 H5B 108.2 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C5 N1 C1 C3 -177.68(13) . . . . ?
C5 N1 C1 C4 64.00(16) . . . . ?
C5 N1 C1 C2 -58.19(17) . . . . ?
C1 N1 C5 C5 174.45(9) . . . 2_655 ?
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              27.43
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.180
_refine_diff_density_min   -0.201
_refine_diff_density_rms    0.047
