# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yanrl1205
_audit_block_doi                 10.5517/cc14482m
_database_code_depnum_ccdc_archive 'CCDC 1046779'
_audit_update_record             
;
2015-02-02 deposited with the CCDC.
2015-03-10 downloaded from the CCDC.
;
_audit_creation_date             2014-12-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H19 N2'
_chemical_formula_sum            'C22 H19 N2'
_chemical_formula_weight         311.39
_chemical_melting_point          ?
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.7108(3)
_cell_length_b                   11.3687(3)
_cell_length_c                   14.8851(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.059(3)
_cell_angle_gamma                90.00
_cell_volume                     1630.84(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2030
_cell_measurement_temperature    291.89(10)
_cell_measurement_theta_max      27.6240
_cell_measurement_theta_min      3.8370
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7034
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.58
_diffrn_ambient_temperature      291.89(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   40.00   77.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946 -178.0000   90.0000 37

#__ type_ start__ end____ width___ exp.time_
  2 omega   38.00   96.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946 -178.0000  150.0000 58

#__ type_ start__ end____ width___ exp.time_
  3 omega   -3.00   45.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -99.0000  -60.0000 48

#__ type_ start__ end____ width___ exp.time_
  4 omega  -51.00   45.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -38.0000  150.0000 96
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0651463000
_diffrn_orient_matrix_UB_12      -0.0244277000
_diffrn_orient_matrix_UB_13      0.0171470000
_diffrn_orient_matrix_UB_21      -0.0334458000
_diffrn_orient_matrix_UB_22      -0.0525786000
_diffrn_orient_matrix_UB_23      0.0110945000
_diffrn_orient_matrix_UB_31      0.0072167000
_diffrn_orient_matrix_UB_32      -0.0230781000
_diffrn_orient_matrix_UB_33      -0.0434552000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2538
_reflns_number_total             3201
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0537
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0520P)²+0.7523P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1422
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 0.52548(15) 0.49763(13) 0.84047(11) 0.0223(4) Uani 1 d . . .
H1 H 0.4945 0.5435 0.7966 0.027 Uiso 1 calc . . R
N2 N 0.53970(15) 0.35554(13) 0.94286(11) 0.0222(4) Uani 1 d . . .
C1 C 0.65508(18) 0.50050(16) 0.88901(13) 0.0211(4) Uani 1 d . . .
C2 C 0.45764(18) 0.41071(16) 0.87420(13) 0.0211(4) Uani 1 d . . .
C3 C 0.66535(19) 0.41310(16) 0.95204(13) 0.0231(4) Uani 1 d . . .
H3 H 0.7424 0.3957 0.9934 0.028 Uiso 1 calc . . R
C4 C 0.75813(18) 0.58999(16) 0.87240(13) 0.0228(4) Uani 1 d . . .
C5 C 0.86572(19) 0.62128(17) 0.93910(14) 0.0274(5) Uani 1 d . . .
H5 H 0.8744 0.5833 0.9948 0.033 Uiso 1 calc . . R
C6 C 0.9599(2) 0.70846(19) 0.92315(15) 0.0324(5) Uani 1 d . . .
H6 H 1.0317 0.7279 0.9679 0.039 Uiso 1 calc . . R
C7 C 0.9470(2) 0.76626(18) 0.84100(16) 0.0338(5) Uani 1 d . . .
H7 H 1.0095 0.8252 0.8305 0.041 Uiso 1 calc . . R
C8 C 0.8411(2) 0.73643(18) 0.77441(16) 0.0323(5) Uani 1 d . . .
H8 H 0.8321 0.7756 0.7191 0.039 Uiso 1 calc . . R
C9 C 0.74783(19) 0.64823(17) 0.78959(14) 0.0277(5) Uani 1 d . . .
H9 H 0.6777 0.6278 0.7439 0.033 Uiso 1 calc . . R
C10 C 0.31056(18) 0.38502(16) 0.84457(13) 0.0223(4) Uani 1 d . . .
C11 C 0.22116(19) 0.48083(17) 0.82560(13) 0.0230(4) Uani 1 d . . .
H11 H 0.2563 0.5570 0.8303 0.028 Uiso 1 calc . . R
C12 C 0.0808(2) 0.46295(18) 0.79989(13) 0.0276(5) Uani 1 d . . .
H12 H 0.0221 0.5272 0.7880 0.033 Uiso 1 calc . . R
C13 C 0.0276(2) 0.35051(18) 0.79188(15) 0.0324(5) Uani 1 d . . .
H13 H -0.0671 0.3389 0.7760 0.039 Uiso 1 calc . . R
C14 C 0.1155(2) 0.25508(19) 0.80753(15) 0.0336(5) Uani 1 d . . .
H14 H 0.0800 0.1792 0.8007 0.040 Uiso 1 calc . . R
C15 C 0.2563(2) 0.27177(17) 0.83337(14) 0.0279(5) Uani 1 d . . .
H15 H 0.3148 0.2071 0.8433 0.034 Uiso 1 calc . . R
C16 C 0.50574(19) 0.26303(16) 1.00546(14) 0.0250(4) Uani 1 d . . .
H16A H 0.4108 0.2375 0.9885 0.030 Uiso 1 calc . . R
H16B H 0.5125 0.2949 1.0663 0.030 Uiso 1 calc . . R
C17 C 0.60152(19) 0.15856(16) 1.00474(13) 0.0235(4) Uani 1 d . . .
C18 C 0.6880(2) 0.12768(17) 1.08200(14) 0.0286(5) Uani 1 d . . .
H18 H 0.6867 0.1715 1.1347 0.034 Uiso 1 calc . . R
C19 C 0.7768(2) 0.03207(18) 1.08172(16) 0.0345(5) Uani 1 d . . .
H19 H 0.8338 0.0116 1.1342 0.041 Uiso 1 calc . . R
C20 C 0.7806(2) -0.03233(19) 1.00400(17) 0.0384(6) Uani 1 d . . .
H20 H 0.8410 -0.0958 1.0036 0.046 Uiso 1 calc . . R
C21 C 0.6948(2) -0.0025(2) 0.92675(16) 0.0402(6) Uani 1 d . . .
H21 H 0.6971 -0.0461 0.8741 0.048 Uiso 1 calc . . R
C22 C 0.6052(2) 0.09194(19) 0.92712(14) 0.0338(5) Uani 1 d . . .
H22 H 0.5469 0.1109 0.8748 0.041 Uiso 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 H1 0.8600 . ?
N1 C1 1.373(2) . ?
N1 C2 1.321(2) . ?
N2 C2 1.368(2) . ?
N2 C3 1.376(2) . ?
N2 C16 1.469(2) . ?
C1 C3 1.362(3) . ?
C1 C4 1.469(3) . ?
C2 C10 1.471(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(3) . ?
C4 C9 1.392(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.380(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.388(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.400(3) . ?
C10 C15 1.393(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.387(3) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.509(3) . ?
C17 C18 1.384(3) . ?
C17 C22 1.386(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.373(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.377(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.383(3) . ?
C22 H22 0.9300 . ?

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 H1 126.7 . . ?
C2 N1 H1 126.7 . . ?
C2 N1 C1 106.59(15) . . ?
C2 N2 C3 106.50(15) . . ?
C2 N2 C16 130.26(16) . . ?
C3 N2 C16 122.86(16) . . ?
N1 C1 C4 121.82(16) . . ?
C3 C1 N1 109.28(16) . . ?
C3 C1 C4 128.87(17) . . ?
N1 C2 N2 110.80(16) . . ?
N1 C2 C10 123.07(16) . . ?
N2 C2 C10 125.99(17) . . ?
N2 C3 H3 126.6 . . ?
C1 C3 N2 106.83(16) . . ?
C1 C3 H3 126.6 . . ?
C5 C4 C1 121.50(18) . . ?
C9 C4 C1 120.15(17) . . ?
C9 C4 C5 118.33(17) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.76(19) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.08(19) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.85(19) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.3(2) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 H9 119.7 . . ?
C8 C9 C4 120.70(19) . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C2 117.46(17) . . ?
C15 C10 C2 123.93(17) . . ?
C15 C10 C11 118.61(17) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.43(18) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.37(18) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.74(18) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.44(19) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.33(18) . . ?
C14 C15 H15 119.8 . . ?
N2 C16 H16A 109.2 . . ?
N2 C16 H16B 109.2 . . ?
N2 C16 C17 111.85(15) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C18 C17 C16 120.36(18) . . ?
C18 C17 C22 118.63(18) . . ?
C22 C17 C16 121.01(18) . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.7(2) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.7(2) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.3(2) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 H22 119.7 . . ?
C21 C22 C17 120.6(2) . . ?
C21 C22 H22 119.7 . . ?

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
N1 C1 C3 N2 -0.4(2) . . . . ?
N1 C1 C4 C5 156.17(18) . . . . ?
N1 C1 C4 C9 -22.0(3) . . . . ?
N1 C2 C10 C11 -38.2(3) . . . . ?
N1 C2 C10 C15 141.0(2) . . . . ?
N2 C2 C10 C11 137.11(19) . . . . ?
N2 C2 C10 C15 -43.7(3) . . . . ?
N2 C16 C17 C18 116.7(2) . . . . ?
N2 C16 C17 C22 -63.1(2) . . . . ?
C1 N1 C2 N2 -0.7(2) . . . . ?
C1 N1 C2 C10 175.20(17) . . . . ?
C1 C4 C5 C6 -178.12(17) . . . . ?
C1 C4 C9 C8 177.26(17) . . . . ?
C2 N1 C1 C3 0.7(2) . . . . ?
C2 N1 C1 C4 -177.53(17) . . . . ?
C2 N2 C3 C1 0.0(2) . . . . ?
C2 N2 C16 C17 126.1(2) . . . . ?
C2 C10 C11 C12 -178.16(17) . . . . ?
C2 C10 C15 C14 178.25(19) . . . . ?
C3 N2 C2 N1 0.5(2) . . . . ?
C3 N2 C2 C10 -175.30(17) . . . . ?
C3 N2 C16 C17 -61.9(2) . . . . ?
C3 C1 C4 C5 -21.7(3) . . . . ?
C3 C1 C4 C9 160.14(19) . . . . ?
C4 C1 C3 N2 177.66(18) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C5 C4 C9 C8 -1.0(3) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C7 C8 C9 C4 1.1(3) . . . . ?
C9 C4 C5 C6 0.1(3) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C10 C15 C14 -2.6(3) . . . . ?
C11 C12 C13 C14 -1.5(3) . . . . ?
C12 C13 C14 C15 1.6(3) . . . . ?
C13 C14 C15 C10 0.5(3) . . . . ?
C15 C10 C11 C12 2.6(3) . . . . ?
C16 N2 C2 N1 173.41(17) . . . . ?
C16 N2 C2 C10 -2.4(3) . . . . ?
C16 N2 C3 C1 -173.61(16) . . . . ?
C16 C17 C18 C19 -179.71(18) . . . . ?
C16 C17 C22 C21 179.02(19) . . . . ?
C17 C18 C19 C20 0.7(3) . . . . ?
C18 C17 C22 C21 -0.8(3) . . . . ?
C18 C19 C20 C21 -0.8(3) . . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
C20 C21 C22 C17 0.7(4) . . . . ?
C22 C17 C18 C19 0.1(3) . . . . ?

_olex2_date_sample_data_collection 2014-12-05
_olex2_submission_special_instructions 'No special instructions were received'
