

data_dr59a

 

_audit_creation_method            SHELXL-97

_chemical_name_systematic

;

 ?

;

_chemical_name_common             ?

_chemical_melting_point           ?

_chemical_formula_moiety          ?

_chemical_formula_sum

 'C19 H24 N2'

_chemical_formula_weight          280.40

 

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'

 

_symmetry_cell_setting            Orthorhombic

_symmetry_space_group_name_H-M    Pca2(1)

 

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                    11.1938(15)

_cell_length_b                    13.9491(19)

_cell_length_c                    10.5219(14)

_cell_angle_alpha                 90.00

_cell_angle_beta                  90.00

_cell_angle_gamma                 90.00

_cell_volume                      1642.9(4)

_cell_formula_units_Z             4

_cell_measurement_temperature     200(2)

_cell_measurement_reflns_used     583

_cell_measurement_theta_min       2.33

_cell_measurement_theta_max       24.69

 

_exptl_crystal_description        plate

_exptl_crystal_colour             colorless

_exptl_crystal_size_max           0.40

_exptl_crystal_size_mid           0.25

_exptl_crystal_size_min           0.05

_exptl_crystal_density_meas       n/a

_exptl_crystal_density_diffrn     1.134

_exptl_crystal_density_method     'not measured'

_exptl_crystal_F_000              608

_exptl_absorpt_coefficient_mu     0.066

_exptl_absorpt_correction_type    multi-scan

_exptl_absorpt_correction_T_min   0.9739

_exptl_absorpt_correction_T_max   0.9967

_exptl_absorpt_process_details    'SADABS, Bruker (2000)'

 

_exptl_special_details

;

 Data collection is performed with three batch runs at phi = 0.00 deg

 (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg

 (650 frames).

 A fourth batch run is collected at phi = 0.00 deg (50 frames) to monitor

 crystal and diffractometer stability. Frame width = 0.30 deg in omega.

 Data is merged, corrected for decay (if any), and treated with multi-scan

 absorption corrections (if required). All symmetry-equivalent reflections

 are merged for centrosymmetric data.

 Friedel pairs are not merged for noncentrosymmetric data.

;

 

_diffrn_ambient_temperature       200(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   'CCD area detector'

_diffrn_measurement_method        'phi and omega scans'

_diffrn_detector_area_resol_mean  ?

_diffrn_standards_number          ?

_diffrn_standards_interval_count  ?

_diffrn_standards_interval_time   ?

_diffrn_standards_decay_%         <1

_diffrn_reflns_number             11584

_diffrn_reflns_av_R_equivalents   0.0383

_diffrn_reflns_av_sigmaI/netI     0.0336

_diffrn_reflns_limit_h_min        -13

_diffrn_reflns_limit_h_max        13

_diffrn_reflns_limit_k_min        -16

_diffrn_reflns_limit_k_max        16

_diffrn_reflns_limit_l_min        -12

_diffrn_reflns_limit_l_max        12

_diffrn_reflns_theta_min          2.33

_diffrn_reflns_theta_max          24.74

_reflns_number_total              2758

_reflns_number_gt                 2230

_reflns_threshold_expression      >2sigma(I)

 

_computing_data_collection        'SMART, Bruker (2000)'

_computing_cell_refinement        'SMART, Bruker (2000)'

_computing_data_reduction         'XPREP, Bruker (2000)'

_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics     'SHELXTL, Bruker (2000)'

_computing_publication_material   'SHELXTL, Bruker (2000)'

 

_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)+(0.0421P)²+0.2058P] 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_abs_structure_details

 'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack    -1(3)

_refine_ls_number_reflns          2758

_refine_ls_number_parameters      190

_refine_ls_number_restraints      1

_refine_ls_R_factor_all           0.0562

_refine_ls_R_factor_gt            0.0371

_refine_ls_wR_factor_ref          0.0916

_refine_ls_wR_factor_gt           0.0828

_refine_ls_goodness_of_fit_ref    1.040

_refine_ls_restrained_S_all       1.039

_refine_ls_shift/su_max           0.001

_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

N1 N -0.03871(15) 0.79809(12) 0.82627(16) 0.0398(4) Uani 1 1 d . . .

N2 N 0.11470(14) 0.73522(12) 0.94432(16) 0.0384(4) Uani 1 1 d . . .

C1 C -0.08099(18) 0.85460(14) 0.92873(19) 0.0382(5) Uani 1 1 d . . .

C2 C -0.18432(19) 0.90926(15) 0.9231(2) 0.0456(5) Uani 1 1 d . . .

H2A H -0.2354 0.9053 0.8512 0.055 Uiso 1 1 calc R . .

C3 C -0.2129(2) 0.97098(16) 1.0252(2) 0.0508(6) Uani 1 1 d . . .

H3A H -0.2827 1.0096 1.0203 0.061 Uiso 1 1 calc R . .

C4 C -0.1424(2) 0.97616(16) 1.1303(2) 0.0496(6) Uani 1 1 d . . .

H4A H -0.1618 1.0201 1.1962 0.060 Uiso 1 1 calc R . .

C5 C -0.04134(19) 0.91720(15) 1.1426(2) 0.0440(6) Uani 1 1 d . . .

C6 C 0.0315(2) 0.91641(18) 1.2524(2) 0.0535(6) Uani 1 1 d . . .

H6A H 0.0124 0.9570 1.3220 0.064 Uiso 1 1 calc R . .

C7 C 0.1282(2) 0.85846(19) 1.2592(2) 0.0544(6) Uani 1 1 d . . .

H7A H 0.1756 0.8591 1.3341 0.065 Uiso 1 1 calc R . .

C8 C 0.1606(2) 0.79757(16) 1.1590(2) 0.0477(6) Uani 1 1 d . . .

H8A H 0.2296 0.7582 1.1657 0.057 Uiso 1 1 calc R . .

C9 C 0.09099(18) 0.79536(14) 1.05019(19) 0.0382(5) Uani 1 1 d . . .

C10 C -0.01015(19) 0.85593(15) 1.0393(2) 0.0378(5) Uani 1 1 d . . .

C11 C 0.0559(2) 0.73770(16) 0.8316(2) 0.0428(5) Uani 1 1 d . . .

C12 C -0.1085(2) 0.79929(17) 0.7060(2) 0.0488(6) Uani 1 1 d . . .

H12A H -0.1411 0.8655 0.6949 0.059 Uiso 1 1 calc R . .

C13 C -0.2140(2) 0.73109(18) 0.7162(3) 0.0661(7) Uani 1 1 d . . .

H13A H -0.2609 0.7468 0.7920 0.099 Uiso 1 1 calc R . .

H13B H -0.1847 0.6651 0.7227 0.099 Uiso 1 1 calc R . .

H13C H -0.2643 0.7374 0.6405 0.099 Uiso 1 1 calc R . .

C14 C -0.0315(2) 0.7772(2) 0.5910(2) 0.0650(7) Uani 1 1 d . . .

H14A H 0.0354 0.8224 0.5875 0.098 Uiso 1 1 calc R . .

H14B H -0.0796 0.7832 0.5136 0.098 Uiso 1 1 calc R . .

H14C H -0.0005 0.7117 0.5977 0.098 Uiso 1 1 calc R . .

C15 C 0.21181(17) 0.66413(15) 0.9510(2) 0.0420(5) Uani 1 1 d . . .

H15A H 0.2729 0.6879 1.0112 0.050 Uiso 1 1 calc R . .

H15B H 0.2499 0.6599 0.8662 0.050 Uiso 1 1 calc R . .

C16 C 0.17489(17) 0.56233(15) 0.9922(2) 0.0411(5) Uani 1 1 d . . .

C17 C 0.1020(2) 0.56246(17) 1.1149(2) 0.0478(6) Uani 1 1 d . . .

H17A H 0.1483 0.5932 1.1827 0.072 Uiso 1 1 calc R . .

H17B H 0.0835 0.4963 1.1393 0.072 Uiso 1 1 calc R . .

H17C H 0.0276 0.5980 1.1016 0.072 Uiso 1 1 calc R . .

C18 C 0.1020(2) 0.51348(18) 0.8876(2) 0.0572(6) Uani 1 1 d . . .

H18A H 0.0795 0.4489 0.9152 0.086 Uiso 1 1 calc R . .

H18B H 0.1500 0.5093 0.8099 0.086 Uiso 1 1 calc R . .

H18C H 0.0297 0.5510 0.8706 0.086 Uiso 1 1 calc R . .

C19 C 0.2901(2) 0.50612(19) 1.0109(3) 0.0683(8) Uani 1 1 d . . .

H19A H 0.3379 0.5365 1.0778 0.102 Uiso 1 1 calc R . .

H19B H 0.3356 0.5055 0.9313 0.102 Uiso 1 1 calc R . .

H19C H 0.2710 0.4402 1.0358 0.102 Uiso 1 1 calc R . .

 


 

_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

N1 C11 1.354(3) . ?

N1 C1 1.417(3) . ?

N1 C12 1.487(3) . ?

N2 C11 1.357(3) . ?

N2 C9 1.420(3) . ?

N2 C15 1.473(2) . ?

C1 C2 1.387(3) . ?

C1 C10 1.408(3) . ?

C2 C3 1.413(3) . ?

C3 C4 1.361(3) . ?

C4 C5 1.405(3) . ?

C5 C6 1.415(3) . ?

C5 C10 1.426(3) . ?

C6 C7 1.353(3) . ?

C7 C8 1.401(3) . ?

C8 C9 1.385(3) . ?

C9 C10 1.417(3) . ?

C12 C13 1.520(3) . ?

C12 C14 1.517(3) . ?

C15 C16 1.541(3) . ?

C16 C19 1.522(3) . ?

C16 C18 1.530(3) . ?

C16 C17 1.528(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

C11 N1 C1 125.16(18) . . ?

C11 N1 C12 116.92(17) . . ?

C1 N1 C12 117.77(16) . . ?

C11 N2 C9 125.46(17) . . ?

C11 N2 C15 114.63(17) . . ?

C9 N2 C15 119.90(16) . . ?

C2 C1 C10 119.9(2) . . ?

C2 C1 N1 123.49(19) . . ?

C10 C1 N1 116.60(17) . . ?

C1 C2 C3 119.4(2) . . ?

C4 C3 C2 121.3(2) . . ?

C3 C4 C5 120.7(2) . . ?

C4 C5 C6 123.0(2) . . ?

C4 C5 C10 118.6(2) . . ?

C6 C5 C10 118.5(2) . . ?

C7 C6 C5 120.6(2) . . ?

C6 C7 C8 122.0(2) . . ?

C7 C8 C9 119.3(2) . . ?

C8 C9 N2 123.83(19) . . ?

C8 C9 C10 120.20(19) . . ?

N2 C9 C10 115.97(17) . . ?

C1 C10 C9 120.61(19) . . ?

C1 C10 C5 119.98(19) . . ?

C9 C10 C5 119.40(19) . . ?

N1 C11 N2 115.55(19) . . ?

N1 C12 C13 109.93(19) . . ?

N1 C12 C14 112.23(18) . . ?

C13 C12 C14 111.7(2) . . ?

N2 C15 C16 115.83(16) . . ?

C19 C16 C18 108.41(19) . . ?

C19 C16 C17 110.06(18) . . ?

C18 C16 C17 108.91(17) . . ?

C19 C16 C15 106.49(17) . . ?

C18 C16 C15 110.56(18) . . ?

C17 C16 C15 112.32(18) . . ?

 

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

C11 N1 C1 C2 -174.2(2) . . . . ?

C12 N1 C1 C2 1.1(3) . . . . ?

C11 N1 C1 C10 7.9(3) . . . . ?

C12 N1 C1 C10 -176.93(17) . . . . ?

C10 C1 C2 C3 4.4(3) . . . . ?

N1 C1 C2 C3 -173.52(18) . . . . ?

C1 C2 C3 C4 -1.5(3) . . . . ?

C2 C3 C4 C5 -2.6(3) . . . . ?

C3 C4 C5 C6 -176.9(2) . . . . ?

C3 C4 C5 C10 3.7(3) . . . . ?

C4 C5 C6 C7 -179.8(2) . . . . ?

C10 C5 C6 C7 -0.3(3) . . . . ?

C5 C6 C7 C8 0.2(3) . . . . ?

C6 C7 C8 C9 -0.9(3) . . . . ?

C7 C8 C9 N2 -178.9(2) . . . . ?

C7 C8 C9 C10 1.6(3) . . . . ?

C11 N2 C9 C8 -173.1(2) . . . . ?

C15 N2 C9 C8 5.5(3) . . . . ?

C11 N2 C9 C10 6.4(3) . . . . ?

C15 N2 C9 C10 -174.94(17) . . . . ?

C2 C1 C10 C9 175.47(18) . . . . ?

N1 C1 C10 C9 -6.5(3) . . . . ?

C2 C1 C10 C5 -3.2(3) . . . . ?

N1 C1 C10 C5 174.82(17) . . . . ?

C8 C9 C10 C1 179.62(19) . . . . ?

N2 C9 C10 C1 0.1(3) . . . . ?

C8 C9 C10 C5 -1.7(3) . . . . ?

N2 C9 C10 C5 178.80(18) . . . . ?

C4 C5 C10 C1 -0.8(3) . . . . ?

C6 C5 C10 C1 179.74(19) . . . . ?

C4 C5 C10 C9 -179.51(19) . . . . ?

C6 C5 C10 C9 1.0(3) . . . . ?

C1 N1 C11 N2 -2.1(3) . . . . ?

C12 N1 C11 N2 -177.32(18) . . . . ?

C9 N2 C11 N1 -5.4(3) . . . . ?

C15 N2 C11 N1 175.84(17) . . . . ?

C11 N1 C12 C13 94.2(2) . . . . ?

C1 N1 C12 C13 -81.4(2) . . . . ?

C11 N1 C12 C14 -30.8(3) . . . . ?

C1 N1 C12 C14 153.56(19) . . . . ?

C11 N2 C15 C16 -87.0(2) . . . . ?

C9 N2 C15 C16 94.2(2) . . . . ?

N2 C15 C16 C19 -171.91(19) . . . . ?

N2 C15 C16 C18 70.5(2) . . . . ?

N2 C15 C16 C17 -51.4(2) . . . . ?

 

_diffrn_measured_fraction_theta_max    0.986

_diffrn_reflns_theta_full              24.74

_diffrn_measured_fraction_theta_full   0.986

_refine_diff_density_max    0.140

_refine_diff_density_min   -0.114

_refine_diff_density_rms    0.027

