 
data_01_JK665
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety         'C18 H22 N4' 
_chemical_formula_sum
 'C18 H22 N4' 
_chemical_formula_weight          294.39
_chemical_compound_source   'Synthesized by Dr. Jiri Kaleta'

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 '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'   0.0311   0.0180
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    5.8515(2)
_cell_length_b                    8.3931(3)
_cell_length_c                    16.8969(6)
_cell_angle_alpha                 90
_cell_angle_beta                  93.3070(10)
_cell_angle_gamma                 90
_cell_volume                      828.46(5)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     8040 
_cell_measurement_theta_min       5.2451 
_cell_measurement_theta_max       69.8910 
 
_exptl_crystal_description        bar 
_exptl_crystal_colour             colourless-yellow 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.180          
_exptl_crystal_F_000              316
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.231
_exptl_crystal_size_mid           0.070
_exptl_crystal_size_min           0.045
_exptl_absorpt_coefficient_mu     0.561
_shelx_estimated_absorpt_T_min    0.881
_shelx_estimated_absorpt_T_max    0.975
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.89 
_exptl_absorpt_correction_T_max   0.97 
_exptl_absorpt_process_details    
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_source                    'I\mS  micro-focus sealed tube' 
_diffrn_radiation_monochromator   'Helios Cu  multilayer optic'
_diffrn_measurement_device_type   'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             10305
_diffrn_reflns_av_unetI/netI      0.0123
_diffrn_reflns_av_R_equivalents   0.0186
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          5.244
_diffrn_reflns_theta_max          70.235
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              1577
_reflns_number_gt                 1427
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker Instrument Service v4.2.9' 
_computing_cell_refinement        'SAINT V8.34A (Bruker AXS Inc., 2013)' 
_computing_data_reduction         'SAINT V8.34A (Bruker AXS Inc., 2013)' 
_computing_structure_solution     'XS, VERSION 2013/1' 
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0373P)²+0.6300P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          1577
_refine_ls_number_parameters      103
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0482
_refine_ls_R_factor_gt            0.0445
_refine_ls_wR_factor_ref          0.1201
_refine_ls_wR_factor_gt           0.1181
_refine_ls_goodness_of_fit_ref    1.166
_refine_ls_restrained_S_all       1.166
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
N1 N 0.5781(2) 0.69629(17) 0.57838(8) 0.0266(4) Uani 1 1 d . . . . .
N2 N 0.5287(2) 0.55960(17) 0.61544(8) 0.0255(3) Uani 1 1 d . . . . .
C1 C 0.4762(3) 0.9407(2) 0.51710(10) 0.0269(4) Uani 1 1 d . . . . .
C2 C 0.4099(3) 0.7973(2) 0.55664(9) 0.0236(4) Uani 1 1 d . . . . .
C3 C 0.1798(3) 0.7666(2) 0.57003(10) 0.0270(4) Uani 1 1 d . . . . .
H3 H 0.0626 0.8405 0.5546 0.032 Uiso 1 1 calc R U . . .
C4 C 0.1312(3) 0.6266(2) 0.60605(10) 0.0255(4) Uani 1 1 d . . . . .
H4 H -0.0224 0.5988 0.6153 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3116(3) 0.5244(2) 0.62913(9) 0.0218(4) Uani 1 1 d . . . . .
C6 C 0.2653(3) 0.3682(2) 0.67123(10) 0.0252(4) Uani 1 1 d . . . . .
C7 C 0.4845(3) 0.2772(2) 0.69359(12) 0.0368(5) Uani 1 1 d . . . . .
H7A H 0.5649 0.2538 0.6456 0.055 Uiso 1 1 calc R U . . .
H7B H 0.4467 0.1772 0.7198 0.055 Uiso 1 1 calc R U . . .
H7C H 0.5830 0.3419 0.7298 0.055 Uiso 1 1 calc R U . . .
C8 C 0.1106(3) 0.2655(2) 0.61532(11) 0.0333(4) Uani 1 1 d . . . . .
H8A H -0.0346 0.3211 0.6033 0.050 Uiso 1 1 calc R U . . .
H8B H 0.0808 0.1634 0.6409 0.050 Uiso 1 1 calc R U . . .
H8C H 0.1867 0.2465 0.5660 0.050 Uiso 1 1 calc R U . . .
C9 C 0.1401(3) 0.4044(2) 0.74696(11) 0.0326(4) Uani 1 1 d . . . . .
H9A H -0.0025 0.4616 0.7328 0.049 Uiso 1 1 calc R U . . .
H9B H 0.2382 0.4703 0.7827 0.049 Uiso 1 1 calc R U . . .
H9C H 0.1050 0.3042 0.7735 0.049 Uiso 1 1 calc R U . . .
 
 
_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 C2 1.335(2) . ?
N1 N2 1.346(2) . ?
N2 C5 1.338(2) . ?
C1 C1 1.192(4) 3_676 ?
C1 C2 1.441(2) . ?
C2 C3 1.402(2) . ?
C3 C4 1.361(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.523(2) . ?
C6 C7 1.522(2) . ?
C6 C8 1.535(2) . ?
C6 C9 1.541(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
 
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
C2 N1 N2 119.65(14) . . ?
C5 N2 N1 120.00(14) . . ?
C1 C1 C2 177.7(3) 3_676 . ?
N1 C2 C3 122.58(16) . . ?
N1 C2 C1 116.37(15) . . ?
C3 C2 C1 121.04(15) . . ?
C4 C3 C2 117.30(15) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 118.71(15) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N2 C5 C4 121.74(15) . . ?
N2 C5 C6 117.82(14) . . ?
C4 C5 C6 120.43(14) . . ?
C7 C6 C5 112.23(14) . . ?
C7 C6 C8 109.23(15) . . ?
C5 C6 C8 108.08(14) . . ?
C7 C6 C9 109.09(15) . . ?
C5 C6 C9 108.92(14) . . ?
C8 C6 C9 109.25(14) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
 
_refine_diff_density_max    0.207
_refine_diff_density_min   -0.220
_refine_diff_density_rms    0.046



