# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_18020603
_audit_block_doi                 10.5517/ccdc.csd.cc1zd9wk
_database_code_depnum_ccdc_archive 'CCDC 1829089'
_audit_update_record             
;
2018-03-12 deposited with the CCDC.
2018-04-04 downloaded from the CCDC.
;
_audit_creation_date             2018-02-07
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        J-A
_chemical_formula_moiety         'C36 H28 N2'
_chemical_formula_sum            'C36 H28 N2'
_chemical_formula_weight         488.60
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHN
_chemical_oxdiff_usercomment     TM-AN
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   14.7747(3)
_cell_length_b                   11.8462(3)
_cell_length_c                   13.9054(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2433.78(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2452
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.1930
_cell_measurement_theta_min      5.7330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5070
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.986
_diffrn_reflns_theta_min         4.785
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00  -7.00   1.00   20.00    --  -41.89 -19.00 -90.00  112
  2  ω     33.00 130.00   1.00   87.50    --  107.79 -30.00  90.00   97
  3  ω     85.00 177.00   1.00   87.50    --  107.79  30.00  30.00   92
  4  ω     44.00 108.00   1.00   87.50    --  107.79 -94.00 -60.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0704962000
_diffrn_orient_matrix_UB_12      0.0864747000
_diffrn_orient_matrix_UB_13      -0.0351350000
_diffrn_orient_matrix_UB_21      -0.0339579000
_diffrn_orient_matrix_UB_22      -0.0152935000
_diffrn_orient_matrix_UB_23      -0.1040135000
_diffrn_orient_matrix_UB_31      -0.0688709000
_diffrn_orient_matrix_UB_32      0.0958735000
_diffrn_orient_matrix_UB_33      0.0153080000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2056
_reflns_number_total             2370
_reflns_odcompleteness_completeness 98.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0684P)²+0.4412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1181
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.32023(7) 0.81095(9) 0.14361(8) 0.0282(3) Uani 1 1 d . . . . .
C2 C 0.20748(8) 0.91320(10) 0.23761(9) 0.0243(3) Uani 1 1 d . . . . .
C3 C 0.04686(8) 0.85624(10) 0.23027(9) 0.0234(3) Uani 1 1 d . . . . .
C4 C 0.16050(8) 0.76573(10) 0.12490(9) 0.0234(3) Uani 1 1 d . . . . .
C5 C 0.06879(8) 0.78050(10) 0.15575(8) 0.0231(3) Uani 1 1 d . . . . .
C6 C 0.27544(9) 0.98702(11) 0.27576(9) 0.0281(3) Uani 1 1 d . . . . .
C7 C 0.11528(8) 0.92551(10) 0.26855(9) 0.0241(3) Uani 1 1 d . . . . .
C8 C 0.11196(9) 0.63009(11) 0.00480(9) 0.0306(3) Uani 1 1 d . . . . .
H8 H 0.1252 0.5804 -0.0450 0.037 Uiso 1 1 calc R . . . .
C9 C 0.18058(9) 0.68778(11) 0.04925(9) 0.0277(3) Uani 1 1 d . . . . .
C10 C 0.00022(8) 0.71649(10) 0.10757(9) 0.0264(3) Uani 1 1 d . . . . .
H10 H -0.0598 0.7237 0.1269 0.032 Uiso 1 1 calc R . . . .
C11 C 0.25234(10) 1.06771(11) 0.34073(10) 0.0341(3) Uani 1 1 d . . . . .
H11 H 0.2967 1.1160 0.3644 0.041 Uiso 1 1 calc R . . . .
C12 C 0.37027(9) 0.97309(12) 0.23828(10) 0.0320(3) Uani 1 1 d . . . . .
H12A H 0.4132 0.9970 0.2870 0.038 Uiso 1 1 calc R . . . .
H12B H 0.3787 1.0204 0.1820 0.038 Uiso 1 1 calc R . . . .
C13 C 0.23052(8) 0.82957(10) 0.16907(9) 0.0239(3) Uani 1 1 d . . . . .
C14 C 0.02115(10) 0.64542(11) 0.03404(9) 0.0305(3) Uani 1 1 d . . . . .
H14 H -0.0248 0.6065 0.0026 0.037 Uiso 1 1 calc R . . . .
C15 C 0.09542(9) 1.01015(11) 0.33879(10) 0.0294(3) Uani 1 1 d . . . . .
H15 H 0.0365 1.0180 0.3615 0.035 Uiso 1 1 calc R . . . .
C16 C 0.16180(10) 1.07958(11) 0.37298(11) 0.0346(3) Uani 1 1 d . . . . .
H16 H 0.1475 1.1351 0.4178 0.041 Uiso 1 1 calc R . . . .
C17 C 0.27806(10) 0.67481(12) 0.01943(10) 0.0344(3) Uani 1 1 d . . . . .
H17A H 0.2912 0.7262 -0.0331 0.041 Uiso 1 1 calc R . . . .
H17B H 0.2884 0.5984 -0.0031 0.041 Uiso 1 1 calc R . . . .
C18 C 0.38770(9) 0.85104(12) 0.21206(10) 0.0316(3) Uani 1 1 d . . . . .
H18A H 0.4476 0.8440 0.1841 0.038 Uiso 1 1 calc R . . . .
H18B H 0.3857 0.8049 0.2696 0.038 Uiso 1 1 calc R . . . .
C19 C 0.34062(9) 0.69972(12) 0.10310(10) 0.0325(3) Uani 1 1 d . . . . .
H19A H 0.3332 0.6424 0.1523 0.039 Uiso 1 1 calc R . . . .
H19B H 0.4030 0.6979 0.0814 0.039 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 C13 1.3896(16) . ?
N1 C18 1.4578(17) . ?
N1 C19 1.4643(18) . ?
C2 C6 1.4333(17) . ?
C2 C7 1.4359(18) . ?
C2 C13 1.4162(18) . ?
C3 C3 1.489(2) 4 ?
C3 C5 1.4086(17) . ?
C3 C7 1.4066(17) . ?
C4 C5 1.4319(17) . ?
C4 C9 1.4309(18) . ?
C4 C13 1.4210(18) . ?
C5 C10 1.4319(17) . ?
C6 C11 1.359(2) . ?
C6 C12 1.5039(18) . ?
C7 C15 1.4302(18) . ?
C8 C9 1.3700(19) . ?
C8 C14 1.4137(19) . ?
C9 C17 1.5065(18) . ?
C10 C14 1.3601(19) . ?
C11 C16 1.418(2) . ?
C12 C18 1.513(2) . ?
C15 C16 1.365(2) . ?
C17 C19 1.515(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
C13 N1 C18 115.74(11) . . ?
C13 N1 C19 115.91(11) . . ?
C18 N1 C19 113.81(11) . . ?
C6 C2 C7 119.45(12) . . ?
C13 C2 C6 120.49(12) . . ?
C13 C2 C7 120.05(11) . . ?
C5 C3 C3 119.01(10) . 4 ?
C7 C3 C3 121.92(11) . 4 ?
C7 C3 C5 118.99(11) . . ?
C9 C4 C5 119.69(11) . . ?
C13 C4 C5 119.63(11) . . ?
C13 C4 C9 120.68(11) . . ?
C3 C5 C4 121.06(11) . . ?
C3 C5 C10 121.25(12) . . ?
C10 C5 C4 117.69(11) . . ?
C2 C6 C12 117.22(12) . . ?
C11 C6 C2 119.95(12) . . ?
C11 C6 C12 122.79(12) . . ?
C3 C7 C2 120.61(11) . . ?
C3 C7 C15 121.33(12) . . ?
C15 C7 C2 118.06(11) . . ?
C9 C8 C14 120.57(12) . . ?
C4 C9 C17 117.80(12) . . ?
C8 C9 C4 120.00(12) . . ?
C8 C9 C17 122.17(12) . . ?
C14 C10 C5 121.24(12) . . ?
C6 C11 C16 121.14(12) . . ?
C6 C12 C18 110.30(11) . . ?
N1 C13 C2 120.78(11) . . ?
N1 C13 C4 119.99(11) . . ?
C2 C13 C4 119.22(11) . . ?
C10 C14 C8 120.76(12) . . ?
C16 C15 C7 120.85(13) . . ?
C15 C16 C11 120.51(13) . . ?
C9 C17 C19 110.61(11) . . ?
N1 C18 C12 110.62(11) . . ?
N1 C19 C17 110.20(12) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.207
_oxdiff_exptl_absorpt_empirical_full_min 0.863
