# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013


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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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#  fide research purposes only. It may contain copyright material 
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data_p21n
_database_code_depnum_ccdc_archive 'CCDC 849623'
#TrackingRef 'DK_JKD77_p21n-final.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N2'
_chemical_formula_sum            'C22 H20 N2'
_chemical_formula_weight         312.40
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           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a                   9.9199(12)
_cell_length_b                   9.5808(11)
_cell_length_c                   18.108(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.506(3)
_cell_angle_gamma                90.00
_cell_volume                     1658.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6044
_cell_measurement_theta_min      4.850
_cell_measurement_theta_max      55.174
_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5583
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS-2008/2
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS-Mo rotating anode'
_diffrn_radiation_monochromator  'INCOATEC mirror optics'
_diffrn_measurement_device_type  'Bruker Smart Apex II with D8-Goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15338
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.35
_reflns_number_total             3033
_reflns_number_gt                2480
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'APEX2 v2010.11'
_computing_cell_refinement       'SAINT V7.68A'
_computing_data_reduction        'SAINT V7.68A'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0791P)^2^+0.7736P] where P=(Fo^2^+2Fc^2^)/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         3033
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1470
_refine_ls_wR_factor_gt          0.1384
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.56060(17) 0.37373(16) 0.16201(9) 0.0222(4) Uani 1 1 d . . .
N2 N 0.07701(17) 0.74806(16) 0.11414(9) 0.0220(4) Uani 1 1 d . . .
C1 C 0.4980(2) 0.50254(19) 0.14218(11) 0.0232(4) Uani 1 1 d . . .
H1 H 0.5372 0.5784 0.1212 0.028 Uiso 1 1 calc R . .
C2 C 0.37088(19) 0.50260(19) 0.15769(10) 0.0222(4) Uani 1 1 d . . .
C3 C 0.3546(2) 0.3679(2) 0.18835(11) 0.0244(4) Uani 1 1 d . . .
H3 H 0.2760 0.3372 0.2046 0.029 Uiso 1 1 calc R . .
C4 C 0.4717(2) 0.29094(19) 0.19022(11) 0.0232(4) Uani 1 1 d . . .
C5 C 0.1306(2) 0.61412(18) 0.12944(10) 0.0218(4) Uani 1 1 d . . .
H5 H 0.0774 0.5321 0.1307 0.026 Uiso 1 1 calc R . .
C6 C 0.2724(2) 0.61985(19) 0.14236(10) 0.0224(4) Uani 1 1 d . . .
C7 C 0.3068(2) 0.7623(2) 0.13376(11) 0.0242(4) Uani 1 1 d . . .
H7 H 0.3983 0.7979 0.1390 0.029 Uiso 1 1 calc R . .
C8 C 0.1870(2) 0.8387(2) 0.11673(11) 0.0236(4) Uani 1 1 d . . .
C9 C 0.1683(2) 0.9913(2) 0.10143(12) 0.0303(5) Uani 1 1 d . . .
H9A H 0.1589 1.0389 0.1477 0.045 Uiso 1 1 calc R . .
H9B H 0.0838 1.0071 0.0595 0.045 Uiso 1 1 calc R . .
H9C H 0.2498 1.0283 0.0870 0.045 Uiso 1 1 calc R . .
C10 C 0.5048(2) 0.1427(2) 0.21344(12) 0.0289(5) Uani 1 1 d . . .
H10A H 0.4240 0.0996 0.2259 0.043 Uiso 1 1 calc R . .
H10B H 0.5857 0.1396 0.2585 0.043 Uiso 1 1 calc R . .
H10C H 0.5265 0.0916 0.1712 0.043 Uiso 1 1 calc R . .
C11 C 0.6898(2) 0.33619(18) 0.14761(11) 0.0218(4) Uani 1 1 d . . .
C12 C 0.7998(2) 0.2847(2) 0.20559(11) 0.0250(4) Uani 1 1 d . . .
H12 H 0.7888 0.2711 0.2556 0.030 Uiso 1 1 calc R . .
C13 C 0.9256(2) 0.2531(2) 0.19003(12) 0.0276(5) Uani 1 1 d . . .
H13 H 1.0008 0.2168 0.2295 0.033 Uiso 1 1 calc R . .
C14 C 0.9425(2) 0.27403(19) 0.11731(12) 0.0251(4) Uani 1 1 d . . .
H14 H 1.0294 0.2536 0.1071 0.030 Uiso 1 1 calc R . .
C15 C 0.8322(2) 0.3248(2) 0.05968(11) 0.0258(4) Uani 1 1 d . . .
H15 H 0.8436 0.3395 0.0098 0.031 Uiso 1 1 calc R . .
C16 C 0.7058(2) 0.35431(19) 0.07424(11) 0.0241(4) Uani 1 1 d . . .
H16 H 0.6297 0.3870 0.0342 0.029 Uiso 1 1 calc R . .
C17 C -0.0676(2) 0.78015(19) 0.09146(11) 0.0214(4) Uani 1 1 d . . .
C18 C -0.1584(2) 0.69840(19) 0.03631(11) 0.0245(4) Uani 1 1 d . . .
H18 H -0.1231 0.6214 0.0142 0.029 Uiso 1 1 calc R . .
C19 C -0.2996(2) 0.7288(2) 0.01372(11) 0.0274(5) Uani 1 1 d . . .
H19 H -0.3613 0.6714 -0.0230 0.033 Uiso 1 1 calc R . .
C20 C -0.3516(2) 0.8433(2) 0.04451(12) 0.0291(5) Uani 1 1 d . . .
H20 H -0.4485 0.8652 0.0285 0.035 Uiso 1 1 calc R . .
C21 C -0.2605(2) 0.9249(2) 0.09885(12) 0.0296(5) Uani 1 1 d . . .
H21 H -0.2954 1.0038 0.1197 0.035 Uiso 1 1 calc R . .
C22 C -0.1198(2) 0.8935(2) 0.12317(11) 0.0262(5) Uani 1 1 d . . .
H22 H -0.0588 0.9490 0.1614 0.031 Uiso 1 1 calc 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 0.0244(9) 0.0147(8) 0.0274(8) 0.0011(6) 0.0067(7) 0.0023(6)
N2 0.0247(9) 0.0131(8) 0.0280(8) -0.0010(6) 0.0067(7) 0.0003(6)
C1 0.0280(10) 0.0132(9) 0.0270(9) 0.0009(7) 0.0051(8) 0.0019(7)
C2 0.0236(10) 0.0167(9) 0.0246(9) -0.0015(7) 0.0033(8) 0.0030(7)
C3 0.0259(10) 0.0210(10) 0.0263(10) -0.0003(8) 0.0071(8) 0.0007(8)
C4 0.0276(10) 0.0177(10) 0.0235(9) 0.0003(7) 0.0055(8) 0.0002(8)
C5 0.0274(11) 0.0119(9) 0.0259(9) 0.0003(7) 0.0066(8) 0.0022(7)
C6 0.0259(10) 0.0179(9) 0.0230(9) -0.0003(7) 0.0059(8) 0.0036(8)
C7 0.0238(10) 0.0195(10) 0.0277(10) -0.0007(8) 0.0041(8) -0.0007(8)
C8 0.0267(10) 0.0170(10) 0.0258(10) -0.0021(7) 0.0048(8) -0.0025(8)
C9 0.0312(11) 0.0157(10) 0.0404(12) 0.0029(8) 0.0036(9) -0.0004(8)
C10 0.0339(12) 0.0177(10) 0.0364(11) 0.0030(8) 0.0119(9) 0.0032(8)
C11 0.0239(10) 0.0115(9) 0.0287(10) -0.0022(7) 0.0049(8) -0.0011(7)
C12 0.0296(11) 0.0201(10) 0.0237(10) 0.0007(7) 0.0046(8) 0.0019(8)
C13 0.0271(11) 0.0201(10) 0.0313(10) -0.0003(8) 0.0001(8) 0.0028(8)
C14 0.0253(10) 0.0142(9) 0.0363(11) -0.0039(8) 0.0089(9) 0.0001(7)
C15 0.0337(11) 0.0162(9) 0.0282(10) 0.0003(8) 0.0094(8) -0.0016(8)
C16 0.0261(10) 0.0172(9) 0.0269(10) 0.0005(7) 0.0032(8) 0.0020(8)
C17 0.0226(10) 0.0152(9) 0.0269(10) 0.0028(7) 0.0077(8) 0.0021(7)
C18 0.0301(11) 0.0145(9) 0.0297(10) 0.0000(7) 0.0093(8) 0.0006(8)
C19 0.0284(11) 0.0216(10) 0.0308(10) 0.0017(8) 0.0053(8) -0.0034(8)
C20 0.0248(11) 0.0241(10) 0.0385(11) 0.0067(9) 0.0086(9) 0.0032(8)
C21 0.0340(12) 0.0186(10) 0.0377(11) -0.0001(8) 0.0126(9) 0.0065(8)
C22 0.0299(11) 0.0184(10) 0.0303(10) -0.0020(8) 0.0077(8) 0.0002(8)
_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 C4 1.382(2) . ?
N1 C1 1.385(2) . ?
N1 C11 1.421(2) . ?
N2 C8 1.386(2) . ?
N2 C5 1.388(2) . ?
N2 C17 1.416(2) . ?
C1 C2 1.363(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.431(3) . ?
C2 C6 1.466(3) . ?
C3 C4 1.369(3) . ?
C3 H3 0.9500 . ?
C4 C10 1.493(3) . ?
C5 C6 1.364(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.425(3) . ?
C7 C8 1.359(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.490(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.387(3) . ?
C11 C16 1.390(3) . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.392(3) . ?
C17 C18 1.393(3) . ?
C18 C19 1.381(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.391(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.380(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
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
C4 N1 C1 108.73(15) . . ?
C4 N1 C11 128.24(15) . . ?
C1 N1 C11 122.81(16) . . ?
C8 N2 C5 108.45(16) . . ?
C8 N2 C17 126.95(16) . . ?
C5 N2 C17 124.25(15) . . ?
C2 C1 N1 108.80(17) . . ?
C2 C1 H1 125.6 . . ?
N1 C1 H1 125.6 . . ?
C1 C2 C3 106.64(16) . . ?
C1 C2 C6 124.59(17) . . ?
C3 C2 C6 128.74(18) . . ?
C4 C3 C2 108.17(17) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.9 . . ?
C3 C4 N1 107.66(16) . . ?
C3 C4 C10 129.87(18) . . ?
N1 C4 C10 122.41(17) . . ?
C6 C5 N2 108.63(16) . . ?
C6 C5 H5 125.7 . . ?
N2 C5 H5 125.7 . . ?
C5 C6 C7 106.60(16) . . ?
C5 C6 C2 127.32(17) . . ?
C7 C6 C2 126.00(18) . . ?
C8 C7 C6 108.70(17) . . ?
C8 C7 H7 125.7 . . ?
C6 C7 H7 125.7 . . ?
C7 C8 N2 107.61(17) . . ?
C7 C8 C9 128.97(19) . . ?
N2 C8 C9 123.41(18) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 120.00(18) . . ?
C12 C11 N1 121.11(17) . . ?
C16 C11 N1 118.87(17) . . ?
C13 C12 C11 119.55(18) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.42(18) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.72(19) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 120.30(19) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 119.98(18) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C22 C17 C18 119.59(18) . . ?
C22 C17 N2 120.63(17) . . ?
C18 C17 N2 119.78(17) . . ?
C19 C18 C17 120.26(18) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 120.23(19) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 119.21(19) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C22 C21 C20 121.02(19) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C17 119.66(18) . . ?
C21 C22 H22 120.2 . . ?
C17 C22 H22 120.2 . . ?
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
C4 N1 C1 C2 0.2(2) . . . . ?
C11 N1 C1 C2 175.16(16) . . . . ?
N1 C1 C2 C3 0.0(2) . . . . ?
N1 C1 C2 C6 -178.31(16) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C6 C2 C3 C4 178.04(18) . . . . ?
C2 C3 C4 N1 0.3(2) . . . . ?
C2 C3 C4 C10 -176.81(19) . . . . ?
C1 N1 C4 C3 -0.3(2) . . . . ?
C11 N1 C4 C3 -174.89(17) . . . . ?
C1 N1 C4 C10 177.06(17) . . . . ?
C11 N1 C4 C10 2.5(3) . . . . ?
C8 N2 C5 C6 0.7(2) . . . . ?
C17 N2 C5 C6 174.22(16) . . . . ?
N2 C5 C6 C7 -0.7(2) . . . . ?
N2 C5 C6 C2 -177.43(17) . . . . ?
C1 C2 C6 C5 154.1(2) . . . . ?
C3 C2 C6 C5 -23.8(3) . . . . ?
C1 C2 C6 C7 -22.0(3) . . . . ?
C3 C2 C6 C7 160.08(19) . . . . ?
C5 C6 C7 C8 0.5(2) . . . . ?
C2 C6 C7 C8 177.30(18) . . . . ?
C6 C7 C8 N2 -0.1(2) . . . . ?
C6 C7 C8 C9 -179.05(19) . . . . ?
C5 N2 C8 C7 -0.3(2) . . . . ?
C17 N2 C8 C7 -173.67(17) . . . . ?
C5 N2 C8 C9 178.68(18) . . . . ?
C17 N2 C8 C9 5.3(3) . . . . ?
C4 N1 C11 C12 -58.3(3) . . . . ?
C1 N1 C11 C12 127.8(2) . . . . ?
C4 N1 C11 C16 122.9(2) . . . . ?
C1 N1 C11 C16 -51.0(2) . . . . ?
C16 C11 C12 C13 0.7(3) . . . . ?
N1 C11 C12 C13 -178.07(17) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C14 C15 C16 C11 1.6(3) . . . . ?
C12 C11 C16 C15 -1.8(3) . . . . ?
N1 C11 C16 C15 176.98(17) . . . . ?
C8 N2 C17 C22 -51.0(3) . . . . ?
C5 N2 C17 C22 136.66(19) . . . . ?
C8 N2 C17 C18 128.4(2) . . . . ?
C5 N2 C17 C18 -44.0(3) . . . . ?
C22 C17 C18 C19 -0.6(3) . . . . ?
N2 C17 C18 C19 -179.94(17) . . . . ?
C17 C18 C19 C20 1.5(3) . . . . ?
C18 C19 C20 C21 -0.9(3) . . . . ?
C19 C20 C21 C22 -0.6(3) . . . . ?
C20 C21 C22 C17 1.6(3) . . . . ?
C18 C17 C22 C21 -0.9(3) . . . . ?
N2 C17 C22 C21 178.41(17) . . . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.067


data_JKDX09B
_database_code_depnum_ccdc_archive 'CCDC 849627'
#TrackingRef 'DK_jkdx09b_c2c-final.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H21 N O2'
_chemical_formula_sum            'C26 H21 N O2'
_chemical_formula_weight         379.44
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_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'
'-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                   17.313(3)
_cell_length_b                   12.727(2)
_cell_length_c                   8.9581(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.106(8)
_cell_angle_gamma                90.00
_cell_volume                     1970.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9899
_cell_measurement_theta_min      8.626
_cell_measurement_theta_max      135.561
_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8777
_exptl_absorpt_correction_T_max  0.9871
_exptl_absorpt_process_details   SADABS-2008/2
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Bruker SMART-Cu rotating anode'
_diffrn_radiation_monochromator  'INCOATEC mirror optics'
_diffrn_measurement_device_type  'Bruker Smart-6000'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16522
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.31
_diffrn_reflns_theta_max         68.37
_reflns_number_total             1777
_reflns_number_gt                1638
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'APEX2 v2010.7'
_computing_cell_refinement       'SAINT V7.68A'
_computing_data_reduction        'SAINT V7.68A'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0344P)^2^+1.1568P] where P=(Fo^2^+2Fc^2^)/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         1777
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0790
_refine_ls_wR_factor_gt          0.0761
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.0000 1.12193(10) 0.2500 0.0224(3) Uani 1 2 d S . .
O1 O 0.13855(4) 0.83988(6) 0.16084(8) 0.0306(2) Uani 1 1 d . . .
C1 C 0.0000 1.45251(14) 0.2500 0.0419(4) Uani 1 2 d S . .
H1 H 0.0000 1.5271 0.2500 0.050 Uiso 1 2 calc SR . .
C2 C -0.05031(7) 1.39768(10) 0.15389(15) 0.0388(3) Uani 1 1 d . . .
H2 H -0.0848 1.4351 0.0870 0.047 Uiso 1 1 calc R . .
C3 C -0.05120(7) 1.28873(9) 0.15376(13) 0.0306(3) Uani 1 1 d . . .
H3 H -0.0867 1.2519 0.0882 0.037 Uiso 1 1 calc R . .
C4 C 0.0000 1.23338(12) 0.2500 0.0250(3) Uani 1 2 d S . .
C5 C 0.04556(6) 1.05782(8) 0.34359(11) 0.0228(2) Uani 1 1 d . . .
H5 H 0.0821 1.0812 0.4192 0.027 Uiso 1 1 calc R . .
C6 C 0.02924(6) 0.95574(8) 0.30921(11) 0.0222(2) Uani 1 1 d . . .
C7 C 0.06667(6) 0.86116(8) 0.38049(11) 0.0234(2) Uani 1 1 d . . .
H7A H 0.0260 0.8096 0.4021 0.028 Uiso 1 1 calc R . .
H7B H 0.0926 0.8822 0.4771 0.028 Uiso 1 1 calc R . .
C8 C 0.12588(6) 0.80786(8) 0.28560(11) 0.0234(2) Uani 1 1 d . . .
C9 C 0.16800(6) 0.71425(8) 0.34924(11) 0.0228(2) Uani 1 1 d . . .
C10 C 0.15011(6) 0.66920(9) 0.48499(12) 0.0266(3) Uani 1 1 d . . .
H10 H 0.1101 0.6985 0.5403 0.032 Uiso 1 1 calc R . .
C11 C 0.19025(6) 0.58198(9) 0.53988(13) 0.0297(3) Uani 1 1 d . . .
H11 H 0.1777 0.5517 0.6324 0.036 Uiso 1 1 calc R . .
C12 C 0.24875(6) 0.53896(9) 0.45978(12) 0.0291(3) Uani 1 1 d . . .
H12 H 0.2758 0.4786 0.4967 0.035 Uiso 1 1 calc R . .
C13 C 0.26791(6) 0.58387(9) 0.32592(12) 0.0298(3) Uani 1 1 d . . .
H13 H 0.3086 0.5549 0.2721 0.036 Uiso 1 1 calc R . .
C14 C 0.22791(6) 0.67068(9) 0.27053(12) 0.0277(3) Uani 1 1 d . . .
H14 H 0.2412 0.7010 0.1784 0.033 Uiso 1 1 calc 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 0.0213(6) 0.0227(7) 0.0236(6) 0.000 0.0032(5) 0.000
O1 0.0310(4) 0.0350(5) 0.0264(4) 0.0040(3) 0.0055(3) 0.0045(3)
C1 0.0483(11) 0.0233(9) 0.0557(11) 0.000 0.0173(9) 0.000
C2 0.0402(7) 0.0315(7) 0.0453(7) 0.0069(6) 0.0098(6) 0.0092(5)
C3 0.0297(6) 0.0299(6) 0.0326(6) 0.0009(5) 0.0059(5) 0.0032(5)
C4 0.0254(7) 0.0235(8) 0.0270(7) 0.000 0.0105(6) 0.000
C5 0.0193(5) 0.0271(6) 0.0220(5) -0.0006(4) 0.0015(4) 0.0007(4)
C6 0.0193(5) 0.0257(6) 0.0220(5) 0.0003(4) 0.0043(4) 0.0006(4)
C7 0.0215(5) 0.0257(6) 0.0231(5) -0.0001(4) 0.0003(4) 0.0007(4)
C8 0.0208(5) 0.0257(6) 0.0235(5) -0.0020(4) 0.0000(4) -0.0036(4)
C9 0.0204(5) 0.0229(5) 0.0249(5) -0.0035(4) -0.0012(4) -0.0014(4)
C10 0.0241(5) 0.0272(6) 0.0287(6) -0.0009(4) 0.0035(4) 0.0025(4)
C11 0.0293(6) 0.0291(6) 0.0308(6) 0.0036(5) 0.0021(4) 0.0019(5)
C12 0.0262(6) 0.0254(6) 0.0352(6) -0.0018(5) -0.0025(5) 0.0026(4)
C13 0.0250(6) 0.0313(6) 0.0331(6) -0.0071(5) 0.0026(4) 0.0045(5)
C14 0.0267(6) 0.0299(6) 0.0267(5) -0.0025(4) 0.0030(4) -0.0001(4)
_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 C5 1.3853(13) 2 ?
N1 C5 1.3854(13) . ?
N1 C4 1.4184(19) . ?
O1 C8 1.2205(13) . ?
C1 C2 1.3805(16) . ?
C1 C2 1.3805(16) 2 ?
C1 H1 0.9500 . ?
C2 C3 1.3866(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3938(14) . ?
C3 H3 0.9500 . ?
C4 C3 1.3939(14) 2 ?
C5 C6 1.3613(15) . ?
C5 H5 0.9500 . ?
C6 C6 1.426(2) 2 ?
C6 C7 1.4939(14) . ?
C7 C8 1.5258(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.4937(15) . ?
C9 C10 1.3944(15) . ?
C9 C14 1.3999(15) . ?
C10 C11 1.3856(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3853(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3848(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.3818(16) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
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 C5 107.83(12) 2 . ?
C5 N1 C4 126.08(6) 2 . ?
C5 N1 C4 126.08(6) . . ?
C2 C1 C2 119.27(16) . 2 ?
C2 C1 H1 120.4 . . ?
C2 C1 H1 120.4 2 . ?
C1 C2 C3 120.84(12) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C4 119.88(12) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C3 119.28(15) . 2 ?
C3 C4 N1 120.36(7) . . ?
C3 C4 N1 120.36(7) 2 . ?
C6 C5 N1 108.71(9) . . ?
C6 C5 H5 125.6 . . ?
N1 C5 H5 125.6 . . ?
C5 C6 C6 107.37(6) . 2 ?
C5 C6 C7 126.33(9) . . ?
C6 C6 C7 126.29(6) 2 . ?
C6 C7 C8 114.15(9) . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O1 C8 C9 120.50(9) . . ?
O1 C8 C7 121.41(10) . . ?
C9 C8 C7 118.09(9) . . ?
C10 C9 C14 118.83(10) . . ?
C10 C9 C8 122.27(9) . . ?
C14 C9 C8 118.90(9) . . ?
C11 C10 C9 120.53(10) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 119.97(10) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.10(10) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.14(10) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 120.42(10) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
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
C2 C1 C2 C3 0.49(8) 2 . . . ?
C1 C2 C3 C4 -0.98(16) . . . . ?
C2 C3 C4 C3 0.48(8) . . . 2 ?
C2 C3 C4 N1 -179.52(8) . . . . ?
C5 N1 C4 C3 2.68(7) 2 . . . ?
C5 N1 C4 C3 -177.32(7) . . . . ?
C5 N1 C4 C3 -177.31(7) 2 . . 2 ?
C5 N1 C4 C3 2.68(7) . . . 2 ?
C5 N1 C5 C6 0.24(5) 2 . . . ?
C4 N1 C5 C6 -179.76(5) . . . . ?
N1 C5 C6 C6 -0.60(13) . . . 2 ?
N1 C5 C6 C7 178.41(8) . . . . ?
C5 C6 C7 C8 -103.41(12) . . . . ?
C6 C6 C7 C8 75.42(15) 2 . . . ?
C6 C7 C8 O1 -2.04(14) . . . . ?
C6 C7 C8 C9 178.36(9) . . . . ?
O1 C8 C9 C10 -173.80(10) . . . . ?
C7 C8 C9 C10 5.81(15) . . . . ?
O1 C8 C9 C14 6.71(15) . . . . ?
C7 C8 C9 C14 -173.68(9) . . . . ?
C14 C9 C10 C11 -0.87(16) . . . . ?
C8 C9 C10 C11 179.64(10) . . . . ?
C9 C10 C11 C12 0.08(17) . . . . ?
C10 C11 C12 C13 0.90(17) . . . . ?
C11 C12 C13 C14 -1.07(17) . . . . ?
C12 C13 C14 C9 0.26(17) . . . . ?
C10 C9 C14 C13 0.70(16) . . . . ?
C8 C9 C14 C13 -179.79(9) . . . . ?
_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        68.37
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.030