 
data_PB
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C22 H19 N' 
_chemical_formula_weight          297.38

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 n a 21'
_space_group_name_Hall            'P 2c -2n'
 
_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, z+1/2'
 'x+1/2, -y+1/2, z'
 '-x+1/2, y+1/2, z+1/2'
 
_cell_length_a                    7.854(4)
_cell_length_b                    22.091(12)
_cell_length_c                    9.597(5)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1665.0(15)
_cell_formula_units_Z             4
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     402
_cell_measurement_theta_min       3.18
_cell_measurement_theta_max       17.56
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.186          
_exptl_crystal_F_000              632
_exptl_transmission_factor_min    0.967
_exptl_transmission_factor_max    0.979
_exptl_crystal_size_max           0.500
_exptl_crystal_size_mid           0.400
_exptl_crystal_size_min           0.380
_exptl_absorpt_coefficient_mu     0.068
_shelx_estimated_absorpt_T_min    0.967
_shelx_estimated_absorpt_T_max    0.974
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    SADABS
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             6233
_diffrn_reflns_av_unetI/netI      0.1177
_diffrn_reflns_av_R_equivalents   0.0701
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -30
_diffrn_reflns_limit_k_max        28
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          3.183
_diffrn_reflns_theta_max          29.004
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.944
_diffrn_measured_fraction_theta_full  0.970
_diffrn_reflns_Laue_measured_fraction_max    0.944
_diffrn_reflns_Laue_measured_fraction_full   0.970
_diffrn_reflns_point_group_measured_fraction_max   0.783
_diffrn_reflns_point_group_measured_fraction_full  0.829
_reflns_number_total              3464
_reflns_number_gt                 1533
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.570
_reflns_Friedel_fraction_max      0.603
_reflns_Friedel_fraction_full     0.669
 
_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 APEX2'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_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)+(0.0476P)²] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef        0.015(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
;
 Flack x determined using 392 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          3464
_refine_ls_number_parameters      210
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.1721
_refine_ls_R_factor_gt            0.0678
_refine_ls_wR_factor_ref          0.1585
_refine_ls_wR_factor_gt           0.1224
_refine_ls_goodness_of_fit_ref    0.992
_refine_ls_restrained_S_all       0.992
_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 0.0900(6) 0.32724(17) 0.4797(5) 0.0502(11) Uani 1 1 d . . . . .
C1 C 0.2039(7) 0.3320(2) 0.5876(6) 0.0476(15) Uani 1 1 d . . . . .
C2 C 0.3428(7) 0.3663(2) 0.5420(5) 0.0422(13) Uani 1 1 d . . . . .
C3 C 0.3105(7) 0.3829(2) 0.4010(5) 0.0430(13) Uani 1 1 d . . . . .
C4 C 0.1555(7) 0.3584(2) 0.3680(6) 0.0488(14) Uani 1 1 d . . . . .
H4 H 0.1021 0.3622 0.2820 0.059 Uiso 1 1 calc R U . . .
C5 C 0.1938(9) 0.3086(2) 0.7218(7) 0.0631(17) Uani 1 1 d . . . . .
H5 H 0.1001 0.2863 0.7512 0.076 Uiso 1 1 calc R U . . .
C6 C 0.3294(11) 0.3202(3) 0.8093(7) 0.079(2) Uani 1 1 d . . . . .
H6 H 0.3278 0.3046 0.8992 0.095 Uiso 1 1 calc R U . . .
C8 C 0.4767(8) 0.3778(2) 0.6343(7) 0.0601(16) Uani 1 1 d . . . . .
H8 H 0.5699 0.4008 0.6063 0.072 Uiso 1 1 calc R U . . .
C7 C 0.4685(10) 0.3547(3) 0.7668(7) 0.078(2) Uani 1 1 d . . . . .
H7 H 0.5569 0.3621 0.8290 0.093 Uiso 1 1 calc R U . . .
C9 C -0.0758(8) 0.2983(2) 0.4864(7) 0.0745(19) Uani 1 1 d . . . . .
H9A H -0.1363 0.3055 0.4011 0.112 Uiso 1 1 calc R U . . .
H9B H -0.1393 0.3147 0.5631 0.112 Uiso 1 1 calc R U . . .
H9C H -0.0613 0.2555 0.4995 0.112 Uiso 1 1 calc R U . . .
C10 C 0.4234(7) 0.4215(2) 0.3075(5) 0.0461(13) Uani 1 1 d . . . . .
H10 H 0.4839 0.4497 0.3688 0.055 Uiso 1 1 calc R U . . .
C11 C 0.3144(7) 0.4599(2) 0.2108(6) 0.0487(14) Uani 1 1 d . . . . .
C12 C 0.3002(7) 0.4477(2) 0.0704(6) 0.0588(17) Uani 1 1 d . . . . .
H12 H 0.3619 0.4159 0.0319 0.071 Uiso 1 1 calc R U . . .
C13 C 0.1947(9) 0.4823(3) -0.0143(8) 0.079(2) Uani 1 1 d . . . . .
H13 H 0.1864 0.4740 -0.1091 0.095 Uiso 1 1 calc R U . . .
C14 C 0.1022(10) 0.5291(3) 0.0440(10) 0.094(3) Uani 1 1 d . . . . .
H14 H 0.0307 0.5522 -0.0120 0.113 Uiso 1 1 calc R U . . .
C15 C 0.1146(9) 0.5418(3) 0.1820(10) 0.090(3) Uani 1 1 d . . . . .
H15 H 0.0522 0.5735 0.2200 0.108 Uiso 1 1 calc R U . . .
C16 C 0.2204(8) 0.5075(2) 0.2661(7) 0.071(2) Uani 1 1 d . . . . .
H16 H 0.2287 0.5164 0.3605 0.086 Uiso 1 1 calc R U . . .
C17 C 0.5593(7) 0.3857(2) 0.2299(5) 0.0432(12) Uani 1 1 d . . . . .
C18 C 0.6988(8) 0.4163(2) 0.1733(6) 0.0540(15) Uani 1 1 d . . . . .
H18 H 0.7093 0.4577 0.1883 0.065 Uiso 1 1 calc R U . . .
C19 C 0.8214(7) 0.3868(3) 0.0959(6) 0.0620(17) Uani 1 1 d . . . . .
H19 H 0.9136 0.4081 0.0599 0.074 Uiso 1 1 calc R U . . .
C20 C 0.8059(8) 0.3256(3) 0.0726(6) 0.0648(17) Uani 1 1 d . . . . .
H20 H 0.8866 0.3052 0.0194 0.078 Uiso 1 1 calc R U . . .
C21 C 0.6706(8) 0.2950(3) 0.1282(7) 0.0652(17) Uani 1 1 d . . . . .
H21 H 0.6605 0.2535 0.1129 0.078 Uiso 1 1 calc R U . . .
C22 C 0.5489(7) 0.3244(2) 0.2066(6) 0.0533(15) Uani 1 1 d . . . . .
H22 H 0.4587 0.3025 0.2442 0.064 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 C1 1.372(7) . ?
N1 C4 1.374(6) . ?
N1 C9 1.452(6) . ?
C1 C5 1.390(8) . ?
C1 C2 1.398(7) . ?
C2 C8 1.399(7) . ?
C2 C3 1.425(6) . ?
C3 C4 1.370(7) . ?
C3 C10 1.522(7) . ?
C5 C6 1.380(9) . ?
C6 C7 1.393(9) . ?
C8 C7 1.372(8) . ?
C10 C11 1.521(7) . ?
C10 C17 1.522(7) . ?
C11 C12 1.379(8) . ?
C11 C16 1.390(7) . ?
C12 C13 1.390(8) . ?
C13 C14 1.383(9) . ?
C14 C15 1.357(10) . ?
C15 C16 1.385(9) . ?
C17 C22 1.376(6) . ?
C17 C18 1.397(7) . ?
C18 C19 1.380(7) . ?
C19 C20 1.376(8) . ?
C20 C21 1.368(7) . ?
C21 C22 1.379(7) . ?
 
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
C1 N1 C4 107.8(4) . . ?
C1 N1 C9 125.8(5) . . ?
C4 N1 C9 126.2(5) . . ?
N1 C1 C5 129.3(6) . . ?
N1 C1 C2 108.3(5) . . ?
C5 C1 C2 122.4(6) . . ?
C1 C2 C8 119.2(5) . . ?
C1 C2 C3 107.3(5) . . ?
C8 C2 C3 133.5(5) . . ?
C4 C3 C2 106.0(5) . . ?
C4 C3 C10 127.1(5) . . ?
C2 C3 C10 126.9(5) . . ?
C3 C4 N1 110.5(5) . . ?
C6 C5 C1 116.8(6) . . ?
C5 C6 C7 121.9(6) . . ?
C7 C8 C2 119.0(6) . . ?
C8 C7 C6 120.8(7) . . ?
C11 C10 C17 112.7(4) . . ?
C11 C10 C3 110.1(4) . . ?
C17 C10 C3 114.0(4) . . ?
C12 C11 C16 118.5(6) . . ?
C12 C11 C10 122.2(5) . . ?
C16 C11 C10 119.2(5) . . ?
C11 C12 C13 120.8(6) . . ?
C14 C13 C12 119.2(7) . . ?
C15 C14 C13 120.8(7) . . ?
C14 C15 C16 119.9(7) . . ?
C15 C16 C11 120.7(7) . . ?
C22 C17 C18 117.3(5) . . ?
C22 C17 C10 123.3(5) . . ?
C18 C17 C10 119.3(4) . . ?
C19 C18 C17 121.9(5) . . ?
C20 C19 C18 119.3(6) . . ?
C21 C20 C19 119.4(6) . . ?
C20 C21 C22 121.3(5) . . ?
C17 C22 C21 120.7(5) . . ?
 
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
C4 N1 C1 C5 179.5(5) . . . . ?
C9 N1 C1 C5 3.8(8) . . . . ?
C4 N1 C1 C2 -0.4(5) . . . . ?
C9 N1 C1 C2 -176.1(4) . . . . ?
N1 C1 C2 C8 179.8(4) . . . . ?
C5 C1 C2 C8 -0.1(7) . . . . ?
N1 C1 C2 C3 0.1(5) . . . . ?
C5 C1 C2 C3 -179.8(5) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C8 C2 C3 C4 -179.4(5) . . . . ?
C1 C2 C3 C10 178.7(4) . . . . ?
C8 C2 C3 C10 -0.9(9) . . . . ?
C2 C3 C4 N1 -0.4(5) . . . . ?
C10 C3 C4 N1 -178.9(5) . . . . ?
C1 N1 C4 C3 0.5(6) . . . . ?
C9 N1 C4 C3 176.2(5) . . . . ?
N1 C1 C5 C6 179.4(5) . . . . ?
C2 C1 C5 C6 -0.7(8) . . . . ?
C1 C5 C6 C7 1.2(9) . . . . ?
C1 C2 C8 C7 0.4(8) . . . . ?
C3 C2 C8 C7 179.9(6) . . . . ?
C2 C8 C7 C6 0.1(9) . . . . ?
C5 C6 C7 C8 -1.0(10) . . . . ?
C4 C3 C10 C11 33.1(7) . . . . ?
C2 C3 C10 C11 -145.2(5) . . . . ?
C4 C3 C10 C17 -94.7(6) . . . . ?
C2 C3 C10 C17 87.1(6) . . . . ?
C17 C10 C11 C12 21.1(7) . . . . ?
C3 C10 C11 C12 -107.3(6) . . . . ?
C17 C10 C11 C16 -161.4(4) . . . . ?
C3 C10 C11 C16 70.1(6) . . . . ?
C16 C11 C12 C13 0.2(8) . . . . ?
C10 C11 C12 C13 177.7(5) . . . . ?
C11 C12 C13 C14 -0.6(9) . . . . ?
C12 C13 C14 C15 0.6(10) . . . . ?
C13 C14 C15 C16 -0.2(11) . . . . ?
C14 C15 C16 C11 -0.1(10) . . . . ?
C12 C11 C16 C15 0.1(8) . . . . ?
C10 C11 C16 C15 -177.4(5) . . . . ?
C11 C10 C17 C22 -105.4(5) . . . . ?
C3 C10 C17 C22 21.0(7) . . . . ?
C11 C10 C17 C18 71.6(6) . . . . ?
C3 C10 C17 C18 -162.0(5) . . . . ?
C22 C17 C18 C19 0.5(8) . . . . ?
C10 C17 C18 C19 -176.6(5) . . . . ?
C17 C18 C19 C20 0.5(8) . . . . ?
C18 C19 C20 C21 -1.0(9) . . . . ?
C19 C20 C21 C22 0.4(9) . . . . ?
C18 C17 C22 C21 -1.1(8) . . . . ?
C10 C17 C22 C21 176.0(5) . . . . ?
C20 C21 C22 C17 0.7(9) . . . . ?
 
_refine_diff_density_max    0.154
_refine_diff_density_min   -0.178
_refine_diff_density_rms    0.043



