 
data_Compound_4a
 
_audit_creation_method            SHELXL-2014
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C25 H17 N3' 
_chemical_formula_weight          359.41

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'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            33
_space_group_name_H-M_alt         'P 21 c n'
_space_group_name_Hall            'P -2n 2a'
 
_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+1/2, y+1/2, -z+1/2'
 'x+1/2, -y, -z'
 'x, -y+1/2, z+1/2'
 
_cell_length_a                    6.0110(4)
_cell_length_b                    9.5419(6)
_cell_length_c                    31.230(3)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1791.2(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     200(2)
_cell_measurement_reflns_used     10533 
_cell_measurement_theta_min       2.23 
_cell_measurement_theta_max       30.99 
 
_exptl_crystal_description        needle 
_exptl_crystal_colour             blue 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     'not measured'              
_exptl_crystal_density_diffrn     1.333          
_exptl_crystal_F_000              752
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.5 
_exptl_crystal_size_mid           0.1 
_exptl_crystal_size_min           0.06 
_exptl_absorpt_coefficient_mu     0.080
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.8577 
_exptl_absorpt_correction_T_max   0.8933 
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       200(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'fine-focus sealed tube'                       
_diffrn_measurement_device_type   'STOE IPDS II' 
_diffrn_measurement_method        'omega scans'
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             17996
_diffrn_reflns_av_unetI/netI      0.0619
_diffrn_reflns_av_R_equivalents   0.0815
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -39
_diffrn_reflns_limit_l_max        39
_diffrn_reflns_theta_min          2.232
_diffrn_reflns_theta_max          26.998
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.997
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.997
_diffrn_reflns_point_group_measured_fraction_max   0.974
_diffrn_reflns_point_group_measured_fraction_full  0.979
_reflns_number_total              3827
_reflns_number_gt                 2424
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.780
_reflns_Friedel_fraction_max      0.945
_reflns_Friedel_fraction_full     0.957
 
_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        'X-Area'
_computing_cell_refinement        'X-Area'
_computing_data_reduction         'X-Area'
_computing_structure_solution     'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement   'SHELXL-2014 (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)+(0.0610P)²+0.2971P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.024(4)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
;
 Flack x determined using 784 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    1.8(10)
_chemical_absolute_configuration  ?
_refine_ls_number_reflns          3827
_refine_ls_number_parameters      254
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0859
_refine_ls_R_factor_gt            0.0441
_refine_ls_wR_factor_ref          0.1398
_refine_ls_wR_factor_gt           0.1008
_refine_ls_goodness_of_fit_ref    1.077
_refine_ls_restrained_S_all       1.077
_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
C1 C 1.1299(9) -0.1127(5) 0.12816(17) 0.0558(13) Uani 1 1 d . . . . .
H1 H 1.0798 -0.1945 0.1152 0.067 Uiso 1 1 calc R U . . .
C2 C 1.3365(8) -0.1146(5) 0.14658(15) 0.0498(12) Uani 1 1 d . . . . .
H2 H 1.4241 -0.1949 0.1460 0.060 Uiso 1 1 calc R U . . .
C3 C 1.4100(9) 0.0049(4) 0.16583(17) 0.0511(12) Uani 1 1 d . . . . .
H3 H 1.5503 0.0078 0.1784 0.061 Uiso 1 1 calc R U . . .
C4 C 1.2747(8) 0.1214(4) 0.16660(15) 0.0450(11) Uani 1 1 d . . . . .
H4 H 1.3213 0.2030 0.1802 0.054 Uiso 1 1 calc R U . . .
C5 C 1.0692(8) 0.1157(4) 0.14695(13) 0.0385(10) Uani 1 1 d . . . . .
C6 C 0.9251(7) 0.2421(4) 0.14467(13) 0.0348(9) Uani 1 1 d . . . . .
C7 C 0.7418(7) 0.2462(4) 0.11754(12) 0.0360(9) Uani 1 1 d . . . . .
H7 H 0.7015 0.1669 0.1021 0.043 Uiso 1 1 calc R U . . .
C8 C 0.6181(7) 0.3695(4) 0.11346(12) 0.0333(9) Uani 1 1 d . . . . .
C9 C 0.6830(7) 0.4808(4) 0.13958(13) 0.0359(9) Uani 1 1 d . . . . .
H9 H 0.6048 0.5648 0.1386 0.043 Uiso 1 1 calc R U . . .
C10 C 0.8630(7) 0.4676(4) 0.16707(13) 0.0336(9) Uani 1 1 d . . . . .
C11 C 0.9349(7) 0.5851(4) 0.19493(13) 0.0353(9) Uani 1 1 d . . . . .
C12 C 1.1474(8) 0.5920(4) 0.21151(13) 0.0389(10) Uani 1 1 d . . . . .
H12 H 1.2503 0.5220 0.2053 0.047 Uiso 1 1 calc R U . . .
C13 C 1.2062(8) 0.7031(4) 0.23731(14) 0.0442(11) Uani 1 1 d . . . . .
H13 H 1.3478 0.7087 0.2492 0.053 Uiso 1 1 calc R U . . .
C14 C 1.0505(9) 0.8057(5) 0.24511(15) 0.0478(11) Uani 1 1 d . . . . .
H14 H 1.0848 0.8827 0.2621 0.057 Uiso 1 1 calc R U . . .
C15 C 0.8428(9) 0.7915(5) 0.22710(16) 0.0521(12) Uani 1 1 d . . . . .
H15 H 0.7389 0.8615 0.2325 0.063 Uiso 1 1 calc R U . . .
C16 C 0.4293(7) 0.3863(4) 0.08465(12) 0.0347(9) Uani 1 1 d . . . . .
C17 C 0.2573(7) 0.4860(4) 0.09152(13) 0.0368(9) Uani 1 1 d . . . . .
H17 H 0.2527 0.5481 0.1144 0.044 Uiso 1 1 calc R U . . .
C18 C 0.0976(7) 0.4784(4) 0.05966(13) 0.0394(10) Uani 1 1 d . . . . .
H18 H -0.0294 0.5337 0.0578 0.047 Uiso 1 1 calc R U . . .
C19 C 0.1601(7) 0.3730(4) 0.03061(14) 0.0369(9) Uani 1 1 d . . . . .
C20 C 0.0367(8) 0.3355(4) -0.00504(14) 0.0452(11) Uani 1 1 d . . . . .
H20 H -0.0959 0.3842 -0.0088 0.054 Uiso 1 1 calc R U . . .
C21 C 0.0837(8) 0.2350(5) -0.03600(15) 0.0507(12) Uani 1 1 d . . . . .
H21 H -0.0232 0.2231 -0.0572 0.061 Uiso 1 1 calc R U . . .
C22 C 0.2696(10) 0.1507(5) -0.03912(15) 0.0514(12) Uani 1 1 d . . . . .
H22 H 0.2702 0.0898 -0.0624 0.062 Uiso 1 1 calc R U . . .
C23 C 0.4561(9) 0.1426(5) -0.01290(15) 0.0490(12) Uani 1 1 d . . . . .
H23 H 0.5654 0.0800 -0.0218 0.059 Uiso 1 1 calc R U . . .
C24 C 0.5019(8) 0.2146(4) 0.02462(14) 0.0424(10) Uani 1 1 d . . . . .
H24 H 0.6383 0.1940 0.0372 0.051 Uiso 1 1 calc R U . . .
C25 C 0.3730(7) 0.3135(4) 0.04623(13) 0.0353(9) Uani 1 1 d . . . . .
N1 N 0.9943(7) -0.0003(3) 0.12755(13) 0.0481(10) Uani 1 1 d . . . . .
N2 N 0.9847(6) 0.3499(3) 0.16964(10) 0.0356(8) Uani 1 1 d . . . . .
N3 N 0.7801(7) 0.6844(4) 0.20249(12) 0.0444(9) Uani 1 1 d . . . . .
 
 
_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
C1 N1 1.347(5) . ?
C1 C2 1.369(7) . ?
C2 C3 1.363(6) . ?
C3 C4 1.377(6) . ?
C4 C5 1.380(6) . ?
C5 N1 1.340(5) . ?
C5 C6 1.487(5) . ?
C6 N2 1.340(5) . ?
C6 C7 1.390(6) . ?
C7 C8 1.398(5) . ?
C8 C9 1.394(5) . ?
C8 C16 1.457(5) . ?
C9 C10 1.387(6) . ?
C10 N2 1.343(5) . ?
C10 C11 1.484(5) . ?
C11 N3 1.349(5) . ?
C11 C12 1.380(6) . ?
C12 C13 1.378(6) . ?
C13 C14 1.376(6) . ?
C14 C15 1.376(7) . ?
C15 N3 1.333(5) . ?
C16 C17 1.421(6) . ?
C16 C25 1.427(6) . ?
C17 C18 1.385(6) . ?
C18 C19 1.405(6) . ?
C19 C20 1.385(6) . ?
C19 C25 1.483(6) . ?
C20 C21 1.391(6) . ?
C21 C22 1.380(7) . ?
C22 C23 1.390(7) . ?
C23 C24 1.386(6) . ?
C24 C25 1.395(6) . ?
 
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 C1 C2 124.5(5) . . ?
C3 C2 C1 117.9(4) . . ?
C2 C3 C4 119.5(5) . . ?
C3 C4 C5 119.2(4) . . ?
N1 C5 C4 122.3(4) . . ?
N1 C5 C6 116.9(4) . . ?
C4 C5 C6 120.7(4) . . ?
N2 C6 C7 123.0(4) . . ?
N2 C6 C5 116.0(4) . . ?
C7 C6 C5 120.9(4) . . ?
C6 C7 C8 120.1(4) . . ?
C9 C8 C7 116.0(4) . . ?
C9 C8 C16 119.7(4) . . ?
C7 C8 C16 124.3(4) . . ?
C10 C9 C8 120.8(4) . . ?
N2 C10 C9 122.6(4) . . ?
N2 C10 C11 116.0(4) . . ?
C9 C10 C11 121.4(3) . . ?
N3 C11 C12 122.6(4) . . ?
N3 C11 C10 115.7(4) . . ?
C12 C11 C10 121.7(4) . . ?
C13 C12 C11 119.6(4) . . ?
C14 C13 C12 118.5(4) . . ?
C13 C14 C15 118.3(4) . . ?
N3 C15 C14 124.6(4) . . ?
C17 C16 C25 106.3(3) . . ?
C17 C16 C8 123.1(4) . . ?
C25 C16 C8 130.6(4) . . ?
C18 C17 C16 111.2(4) . . ?
C17 C18 C19 108.4(4) . . ?
C20 C19 C18 124.1(4) . . ?
C20 C19 C25 128.9(4) . . ?
C18 C19 C25 107.0(4) . . ?
C19 C20 C21 128.9(5) . . ?
C22 C21 C20 128.0(4) . . ?
C21 C22 C23 130.0(4) . . ?
C24 C23 C22 129.1(5) . . ?
C23 C24 C25 129.3(4) . . ?
C24 C25 C16 127.2(4) . . ?
C24 C25 C19 125.4(4) . . ?
C16 C25 C19 107.2(3) . . ?
C5 N1 C1 116.6(4) . . ?
C6 N2 C10 117.5(4) . . ?
C15 N3 C11 116.4(4) . . ?
 
_refine_diff_density_max    0.218
_refine_diff_density_min   -0.235
_refine_diff_density_rms    0.052

_shelxl_version_number 2014-3



