# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_mo_dm11389_0m
_database_code_depnum_ccdc_archive 'CCDC 837117'
_audit_update_record             
;
2011-07-28 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;
#TrackingRef '6494_web_deposit_cif_file_0_ZhangZhiyun_1311837762.mo_dm11389_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H22 N2'
_chemical_formula_weight         434.52

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)/n

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                   14.6334(15)
_cell_length_b                   8.9414(9)
_cell_length_c                   17.7375(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.381(2)
_cell_angle_gamma                90.00
_cell_volume                     2237.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    6344
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      32.25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9727
_exptl_absorpt_correction_T_max  0.9792
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18255
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         29.00
_reflns_number_total             5947
_reflns_number_gt                4763
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0756P)²+0.4445P] where P=(Fo²+2Fc²)/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         5947
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1280
_refine_ls_wR_factor_gt          0.1174
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.40409(6) 0.77063(11) 0.19434(5) 0.01619(19) Uani 1 1 d . . .
N2 N 0.54533(6) 0.56601(10) 0.21138(5) 0.01686(19) Uani 1 1 d . . .
C1 C 0.49967(7) 0.82542(13) 0.21478(6) 0.0157(2) Uani 1 1 d . . .
C2 C 0.52059(8) 0.97717(13) 0.22096(6) 0.0190(2) Uani 1 1 d . . .
H2 H 0.4709 1.0488 0.2113 0.023 Uiso 1 1 calc R . .
C3 C 0.61444(8) 1.02375(13) 0.24138(7) 0.0211(2) Uani 1 1 d . . .
H3 H 0.6291 1.1272 0.2479 0.025 Uiso 1 1 calc R . .
C4 C 0.68694(8) 0.91884(13) 0.25233(7) 0.0211(2) Uani 1 1 d . . .
H4 H 0.7511 0.9508 0.2665 0.025 Uiso 1 1 calc R . .
C5 C 0.66575(8) 0.76749(13) 0.24268(7) 0.0196(2) Uani 1 1 d . . .
H5 H 0.7153 0.6964 0.2483 0.024 Uiso 1 1 calc R . .
C6 C 0.57212(7) 0.72019(12) 0.22489(6) 0.0156(2) Uani 1 1 d . . .
C7 C 0.46341(8) 0.55117(12) 0.14602(6) 0.0164(2) Uani 1 1 d . . .
C8 C 0.39228(7) 0.65195(12) 0.13797(6) 0.0163(2) Uani 1 1 d . . .
C9 C 0.30993(8) 0.64759(13) 0.07210(6) 0.0185(2) Uani 1 1 d . . .
C10 C 0.23622(8) 0.75280(14) 0.06392(7) 0.0232(2) Uani 1 1 d . . .
H10 H 0.2413 0.8299 0.1017 0.028 Uiso 1 1 calc R . .
C11 C 0.15670(9) 0.74450(16) 0.00146(7) 0.0292(3) Uani 1 1 d . . .
H11 H 0.1069 0.8151 -0.0036 0.035 Uiso 1 1 calc R . .
C12 C 0.14988(9) 0.63153(17) -0.05431(7) 0.0317(3) Uani 1 1 d . . .
H12 H 0.0954 0.6263 -0.0976 0.038 Uiso 1 1 calc R . .
C13 C 0.22092(9) 0.52830(16) -0.04722(7) 0.0272(3) Uani 1 1 d . . .
H13 H 0.2146 0.4522 -0.0856 0.033 Uiso 1 1 calc R . .
C14 C 0.30324(8) 0.53255(14) 0.01590(6) 0.0202(2) Uani 1 1 d . . .
C15 C 0.37972(8) 0.42494(13) 0.02420(6) 0.0202(2) Uani 1 1 d . . .
C16 C 0.37793(10) 0.30908(15) -0.03035(7) 0.0270(3) Uani 1 1 d . . .
H16 H 0.3244 0.2993 -0.0741 0.032 Uiso 1 1 calc R . .
C17 C 0.45195(11) 0.21025(15) -0.02147(7) 0.0308(3) Uani 1 1 d . . .
H17 H 0.4486 0.1326 -0.0587 0.037 Uiso 1 1 calc R . .
C18 C 0.53203(11) 0.22314(14) 0.04193(8) 0.0296(3) Uani 1 1 d . . .
H18 H 0.5834 0.1555 0.0473 0.036 Uiso 1 1 calc R . .
C19 C 0.53623(9) 0.33416(13) 0.09658(7) 0.0239(2) Uani 1 1 d . . .
H19 H 0.5906 0.3425 0.1397 0.029 Uiso 1 1 calc R . .
C20 C 0.46062(8) 0.43538(13) 0.08906(6) 0.0189(2) Uani 1 1 d . . .
C21 C 0.35867(7) 0.75571(12) 0.25595(6) 0.0155(2) Uani 1 1 d . . .
C22 C 0.29104(8) 0.64459(13) 0.25330(6) 0.0191(2) Uani 1 1 d . . .
H22 H 0.2757 0.5765 0.2107 0.023 Uiso 1 1 calc R . .
C23 C 0.24603(8) 0.63324(14) 0.31301(7) 0.0225(2) Uani 1 1 d . . .
H23 H 0.2004 0.5567 0.3109 0.027 Uiso 1 1 calc R . .
C24 C 0.26673(8) 0.73176(14) 0.37549(7) 0.0236(2) Uani 1 1 d . . .
H24 H 0.2350 0.7243 0.4156 0.028 Uiso 1 1 calc R . .
C25 C 0.33457(8) 0.84146(14) 0.37850(7) 0.0229(2) Uani 1 1 d . . .
H25 H 0.3499 0.9089 0.4214 0.027 Uiso 1 1 calc R . .
C26 C 0.38046(8) 0.85399(13) 0.31954(6) 0.0191(2) Uani 1 1 d . . .
H26 H 0.4268 0.9296 0.3224 0.023 Uiso 1 1 calc R . .
C27 C 0.54838(8) 0.47295(12) 0.27782(6) 0.0178(2) Uani 1 1 d . . .
C28 C 0.47639(8) 0.37012(13) 0.27648(7) 0.0212(2) Uani 1 1 d . . .
H28 H 0.4250 0.3606 0.2310 0.025 Uiso 1 1 calc R . .
C29 C 0.47944(10) 0.28131(14) 0.34157(8) 0.0273(3) Uani 1 1 d . . .
H29 H 0.4297 0.2123 0.3403 0.033 Uiso 1 1 calc R . .
C30 C 0.55411(10) 0.29246(15) 0.40813(8) 0.0304(3) Uani 1 1 d . . .
H30 H 0.5561 0.2315 0.4524 0.036 Uiso 1 1 calc R . .
C31 C 0.62591(10) 0.39390(16) 0.40925(7) 0.0310(3) Uani 1 1 d . . .
H31 H 0.6775 0.4019 0.4547 0.037 Uiso 1 1 calc R . .
C32 C 0.62375(9) 0.48409(15) 0.34512(7) 0.0252(3) Uani 1 1 d . . .
H32 H 0.6735 0.5534 0.3470 0.030 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 C21 1.4280(13) . ?
N1 C1 1.4347(13) . ?
N1 C8 1.4367(13) . ?
N2 C27 1.4337(14) . ?
N2 C7 1.4358(13) . ?
N2 C6 1.4359(14) . ?
C1 C2 1.3889(16) . ?
C1 C6 1.3931(15) . ?
C2 C3 1.3882(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.3906(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3887(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3880(15) . ?
C5 H5 0.9500 . ?
C7 C8 1.3554(15) . ?
C7 C20 1.4396(15) . ?
C8 C9 1.4395(14) . ?
C9 C10 1.4094(17) . ?
C9 C14 1.4176(16) . ?
C10 C11 1.3794(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.399(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.371(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.4108(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.4534(17) . ?
C15 C16 1.4130(16) . ?
C15 C20 1.4181(16) . ?
C16 C17 1.374(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.397(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.3773(17) . ?
C18 H18 0.9500 . ?
C19 C20 1.4081(17) . ?
C19 H19 0.9500 . ?
C21 C22 1.3943(15) . ?
C21 C26 1.3983(15) . ?
C22 C23 1.3913(15) . ?
C22 H22 0.9500 . ?
C23 C24 1.3849(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.3864(18) . ?
C24 H24 0.9500 . ?
C25 C26 1.3893(16) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.3937(16) . ?
C27 C32 1.3975(16) . ?
C28 C29 1.3922(16) . ?
C28 H28 0.9500 . ?
C29 C30 1.3832(19) . ?
C29 H29 0.9500 . ?
C30 C31 1.384(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.3878(17) . ?
C31 H31 0.9500 . ?
C32 H32 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
C21 N1 C1 117.32(8) . . ?
C21 N1 C8 117.97(9) . . ?
C1 N1 C8 110.94(8) . . ?
C27 N2 C7 116.57(9) . . ?
C27 N2 C6 118.19(8) . . ?
C7 N2 C6 110.86(8) . . ?
C2 C1 C6 120.35(10) . . ?
C2 C1 N1 122.22(10) . . ?
C6 C1 N1 117.36(10) . . ?
C3 C2 C1 119.73(10) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.95(11) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.21(10) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 119.97(10) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 119.68(10) . . ?
C5 C6 N2 122.67(10) . . ?
C1 C6 N2 117.53(9) . . ?
C8 C7 N2 118.49(9) . . ?
C8 C7 C20 121.75(10) . . ?
N2 C7 C20 119.70(10) . . ?
C7 C8 N1 118.07(9) . . ?
C7 C8 C9 121.44(10) . . ?
N1 C8 C9 120.35(9) . . ?
C10 C9 C14 120.25(10) . . ?
C10 C9 C8 121.23(10) . . ?
C14 C9 C8 118.51(10) . . ?
C11 C10 C9 120.41(12) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.58(12) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.74(11) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 121.46(12) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C9 117.56(11) . . ?
C13 C14 C15 122.35(11) . . ?
C9 C14 C15 120.09(10) . . ?
C16 C15 C20 117.62(11) . . ?
C16 C15 C14 122.82(11) . . ?
C20 C15 C14 119.56(10) . . ?
C17 C16 C15 121.48(12) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 120.43(11) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.82(12) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.62(12) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 120.03(10) . . ?
C19 C20 C7 121.36(10) . . ?
C15 C20 C7 118.61(10) . . ?
C22 C21 C26 118.88(10) . . ?
C22 C21 N1 120.74(9) . . ?
C26 C21 N1 120.38(10) . . ?
C23 C22 C21 120.09(10) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 121.03(11) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 118.90(10) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C24 C25 C26 120.81(11) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C25 C26 C21 120.28(11) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
C28 C27 C32 118.90(10) . . ?
C28 C27 N2 120.68(10) . . ?
C32 C27 N2 120.41(10) . . ?
C29 C28 C27 120.28(11) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C30 C29 C28 120.73(12) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C29 C30 C31 118.96(11) . . ?
C29 C30 H30 120.5 . . ?
C31 C30 H30 120.5 . . ?
C30 C31 C32 121.12(12) . . ?
C30 C31 H31 119.4 . . ?
C32 C31 H31 119.4 . . ?
C31 C32 C27 120.00(12) . . ?
C31 C32 H32 120.0 . . ?
C27 C32 H32 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.046


