# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1054186'
_audit_update_record             
;
2015-03-16 deposited with the CCDC.
2015-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H19 N'
_chemical_formula_weight         345.42

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   'P2(1)/c  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.2763(2)
_cell_length_b                   10.2244(3)
_cell_length_c                   19.9092(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.243(2)
_cell_angle_gamma                90.00
_cell_volume                     1883.10(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    288(2)
_cell_measurement_reflns_used    5608
_cell_measurement_theta_min      3.6600
_cell_measurement_theta_max      29.1830

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9725
_exptl_absorpt_correction_T_max  0.9758
_exptl_absorpt_process_details   ?

_exptl_special_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.
;

_diffrn_ambient_temperature      288(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19207
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3696
_reflns_number_gt                3027
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0420P)²+0.4720P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3696
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.36885(11) 0.48019(11) 0.10375(5) 0.0365(3) Uani 1 1 d . . .
C1 C 0.97371(17) 0.41459(18) 0.33317(8) 0.0569(4) Uani 1 1 d . . .
H1A H 1.0508 0.3900 0.3630 0.068 Uiso 1 1 calc R . .
C2 C 0.94014(19) 0.54280(19) 0.32385(9) 0.0671(5) Uani 1 1 d . . .
H2A H 0.9944 0.6062 0.3478 0.081 Uiso 1 1 calc R . .
C3 C 0.82638(18) 0.58057(17) 0.27928(9) 0.0603(4) Uani 1 1 d . . .
H3A H 0.8051 0.6690 0.2737 0.072 Uiso 1 1 calc R . .
C4 C 0.74396(14) 0.48876(14) 0.24297(6) 0.0394(3) Uani 1 1 d . . .
C5 C 0.77898(16) 0.35850(15) 0.25327(7) 0.0480(4) Uani 1 1 d . . .
H5A H 0.7252 0.2945 0.2296 0.058 Uiso 1 1 calc R . .
C6 C 0.89252(18) 0.32192(17) 0.29807(8) 0.0560(4) Uani 1 1 d . . .
H6A H 0.9140 0.2337 0.3045 0.067 Uiso 1 1 calc R . .
C7 C 0.62432(14) 0.52402(14) 0.19236(7) 0.0398(3) Uani 1 1 d . . .
H7A H 0.6267 0.4751 0.1501 0.048 Uiso 1 1 calc R . .
C8 C 0.56215(16) 0.65664(15) 0.18313(7) 0.0476(4) Uani 1 1 d . . .
H8A H 0.5356 0.6853 0.1374 0.057 Uiso 1 1 calc R . .
H8B H 0.6002 0.7250 0.2132 0.057 Uiso 1 1 calc R . .
C9 C 0.46947(14) 0.55115(13) 0.21253(6) 0.0374(3) Uani 1 1 d . . .
C10 C 0.44689(15) 0.56092(14) 0.28356(7) 0.0408(3) Uani 1 1 d . . .
C11 C 0.41952(15) 0.57067(14) 0.34085(7) 0.0419(3) Uani 1 1 d . . .
C12 C 0.38021(14) 0.58517(13) 0.40902(6) 0.0371(3) Uani 1 1 d . . .
C13 C 0.32482(16) 0.48000(16) 0.44307(7) 0.0486(4) Uani 1 1 d . . .
H13A H 0.3140 0.3993 0.4217 0.058 Uiso 1 1 calc R . .
C14 C 0.28589(18) 0.49410(19) 0.50797(8) 0.0595(4) Uani 1 1 d . . .
H14A H 0.2483 0.4233 0.5302 0.071 Uiso 1 1 calc R . .
C15 C 0.30248(18) 0.6125(2) 0.54002(8) 0.0598(5) Uani 1 1 d . . .
H15A H 0.2766 0.6218 0.5840 0.072 Uiso 1 1 calc R . .
C16 C 0.35723(18) 0.71722(17) 0.50723(8) 0.0557(4) Uani 1 1 d . . .
H16A H 0.3682 0.7974 0.5291 0.067 Uiso 1 1 calc R . .
C17 C 0.39622(16) 0.70457(14) 0.44204(7) 0.0460(3) Uani 1 1 d . . .
H17A H 0.4333 0.7761 0.4201 0.055 Uiso 1 1 calc R . .
C18 C 0.34750(14) 0.49477(13) 0.16805(6) 0.0349(3) Uani 1 1 d . . .
C19 C 0.21657(15) 0.46031(15) 0.19527(7) 0.0436(3) Uani 1 1 d . . .
H19A H 0.2051 0.4728 0.2408 0.052 Uiso 1 1 calc R . .
C20 C 0.10764(15) 0.40892(15) 0.15441(7) 0.0459(4) Uani 1 1 d . . .
H20A H 0.0208 0.3863 0.1719 0.055 Uiso 1 1 calc R . .
C21 C 0.12570(14) 0.38970(13) 0.08571(7) 0.0378(3) Uani 1 1 d . . .
C22 C 0.25969(14) 0.42816(12) 0.06197(6) 0.0349(3) Uani 1 1 d . . .
C23 C 0.28012(15) 0.41373(14) -0.00715(7) 0.0428(3) Uani 1 1 d . . .
H23A H 0.3673 0.4386 -0.0236 0.051 Uiso 1 1 calc R . .
C24 C 0.17272(16) 0.36351(15) -0.04996(7) 0.0484(4) Uani 1 1 d . . .
H24A H 0.1872 0.3551 -0.0955 0.058 Uiso 1 1 calc R . .
C25 C 0.04062(16) 0.32433(15) -0.02642(8) 0.0499(4) Uani 1 1 d . . .
H25A H -0.0315 0.2900 -0.0563 0.060 Uiso 1 1 calc R . .
C26 C 0.01789(15) 0.33638(15) 0.03985(8) 0.0465(3) Uani 1 1 d . . .
H26A H -0.0695 0.3093 0.0552 0.056 Uiso 1 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 C18 1.3182(16) . ?
N1 C22 1.3696(17) . ?
C1 C2 1.357(3) . ?
C1 C6 1.369(2) . ?
C2 C3 1.383(2) . ?
C3 C4 1.381(2) . ?
C4 C5 1.383(2) . ?
C4 C7 1.4871(19) . ?
C5 C6 1.381(2) . ?
C7 C8 1.480(2) . ?
C7 C9 1.5449(18) . ?
C8 C9 1.5229(19) . ?
C9 C10 1.4482(17) . ?
C9 C18 1.4996(18) . ?
C10 C11 1.1909(18) . ?
C11 C12 1.4388(18) . ?
C12 C17 1.3893(19) . ?
C12 C13 1.390(2) . ?
C13 C14 1.375(2) . ?
C14 C15 1.372(3) . ?
C15 C16 1.371(2) . ?
C16 C17 1.379(2) . ?
C18 C19 1.4108(18) . ?
C19 C20 1.355(2) . ?
C20 C21 1.4042(19) . ?
C21 C26 1.4128(19) . ?
C21 C22 1.4177(18) . ?
C22 C23 1.4107(18) . ?
C23 C24 1.363(2) . ?
C24 C25 1.402(2) . ?
C25 C26 1.357(2) . ?

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
C18 N1 C22 118.45(11) . . ?
C2 C1 C6 119.13(16) . . ?
C1 C2 C3 120.94(16) . . ?
C4 C3 C2 120.86(16) . . ?
C3 C4 C5 117.54(14) . . ?
C3 C4 C7 123.13(14) . . ?
C5 C4 C7 119.30(12) . . ?
C6 C5 C4 121.09(14) . . ?
C1 C6 C5 120.44(16) . . ?
C8 C7 C4 124.81(12) . . ?
C8 C7 C9 60.42(9) . . ?
C4 C7 C9 121.95(11) . . ?
C7 C8 C9 61.91(9) . . ?
C10 C9 C18 116.48(11) . . ?
C10 C9 C8 116.94(12) . . ?
C18 C9 C8 117.90(11) . . ?
C10 C9 C7 118.07(11) . . ?
C18 C9 C7 116.93(11) . . ?
C8 C9 C7 57.67(9) . . ?
C11 C10 C9 175.91(14) . . ?
C10 C11 C12 177.37(14) . . ?
C17 C12 C13 118.65(12) . . ?
C17 C12 C11 120.75(13) . . ?
C13 C12 C11 120.60(13) . . ?
C14 C13 C12 120.64(15) . . ?
C15 C14 C13 120.09(16) . . ?
C16 C15 C14 120.03(14) . . ?
C15 C16 C17 120.48(15) . . ?
C16 C17 C12 120.10(14) . . ?
N1 C18 C19 122.70(12) . . ?
N1 C18 C9 117.13(11) . . ?
C19 C18 C9 120.17(11) . . ?
C20 C19 C18 119.41(12) . . ?
C19 C20 C21 120.09(12) . . ?
C20 C21 C26 123.63(12) . . ?
C20 C21 C22 117.18(12) . . ?
C26 C21 C22 119.19(12) . . ?
N1 C22 C23 119.11(11) . . ?
N1 C22 C21 122.16(11) . . ?
C23 C22 C21 118.72(12) . . ?
C24 C23 C22 120.32(13) . . ?
C23 C24 C25 121.00(13) . . ?
C26 C25 C24 120.10(13) . . ?
C25 C26 C21 120.66(13) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.034
