# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_20190107liucan
_database_code_depnum_ccdc_archive 'CCDC 1889682'
_audit_update_record             
;
2019-01-09 deposited with the CCDC.	2019-04-30 downloaded from the CCDC.
;
_audit_creation_date             2019-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 N2'
_chemical_formula_sum            'C22 H16 N2'
_chemical_formula_weight         308.37
_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 0.0181 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      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_operation_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                   4.84497(9)
_cell_length_b                   20.0214(4)
_cell_length_c                   15.7697(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.9103(18)
_cell_angle_gamma                90
_cell_volume                     1518.60(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3591
_cell_measurement_temperature    108.9(7)
_cell_measurement_theta_max      71.1640
_cell_measurement_theta_min      3.5670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9190
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.294
_diffrn_reflns_theta_min         3.584
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      108.9(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -16.00   1.00    2.00    --  -40.81 -38.00-120.00   97
  2  ω   -103.00 -16.00   1.00    2.00    --  -40.81 -38.00 -30.00   87
  3  ω    -69.00 -10.00   1.00    2.00    --  -40.81 125.00 120.00   59
  4  ω     23.00  95.00   1.00    2.00    --   40.81-125.00 150.00   72
  5  ω     65.00  95.00   1.00    4.00    --  100.91-125.00-180.00   30
  6  ω     30.00 109.00   1.00    4.00    --  100.91 -95.00-180.00   79
  7  ω     86.00 112.00   1.00    4.00    --  100.91  61.00 -30.00   26
  8  ω     29.00  83.00   1.00    4.00    --  100.91-125.00   0.00   54
  9  ω     19.00 127.00   1.00    4.00    --  100.91 -15.00 -30.00  108
 10  ω     87.00 113.00   1.00    4.00    --  100.91-125.00   0.00   26
 11  ω     31.00 119.00   1.00    4.00    --  100.91 -45.00-180.00   88
 12  ω    134.00 173.00   1.00    4.00    --  100.91  61.00 -30.00   39
 13  ω     84.00 170.00   1.00    4.00    --  100.91  30.00 150.00   86
 14  ω     26.00 132.00   1.00    4.00    --  100.91 -77.00   0.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0494840000
_diffrn_orient_matrix_UB_12      0.0167636000
_diffrn_orient_matrix_UB_13      -0.0960252000
_diffrn_orient_matrix_UB_21      -0.0408966000
_diffrn_orient_matrix_UB_22      -0.0747472000
_diffrn_orient_matrix_UB_23      -0.0209800000
_diffrn_orient_matrix_UB_31      -0.3136739000
_diffrn_orient_matrix_UB_32      0.0071174000
_diffrn_orient_matrix_UB_33      0.0057805000
_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                2451
_reflns_number_total             2899
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.378
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.017
_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)+(0.0511P)²+0.4911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1083
_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:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C12(H12), C14(H14), C15(H15), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_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 0.2335(2) 0.10098(6) 0.27789(8) 0.0256(3) Uani 1 1 d . . . . .
C2 C 0.1035(3) 0.04273(7) 0.24794(10) 0.0239(3) Uani 1 1 d . . . . .
N3 N -0.0716(2) 0.00893(6) 0.28901(8) 0.0251(3) Uani 1 1 d . . . . .
C4 C 0.4143(3) 0.14261(7) 0.42275(10) 0.0247(3) Uani 1 1 d . . . . .
C5 C 0.5526(3) 0.08588(8) 0.45592(10) 0.0285(3) Uani 1 1 d . . . . .
H5 H 0.4996 0.0440 0.4341 0.034 Uiso 1 1 calc R . . . .
C6 C 0.5642(3) 0.18084(8) 0.22033(10) 0.0285(3) Uani 1 1 d . . . . .
H6 H 0.5704 0.2110 0.2654 0.034 Uiso 1 1 calc R . . . .
C7 C -0.1073(3) -0.06803(7) 0.16649(10) 0.0260(3) Uani 1 1 d . . . . .
C8 C 0.4013(3) 0.12335(7) 0.21831(10) 0.0253(3) Uani 1 1 d . . . . .
C9 C 0.4970(3) 0.20446(8) 0.45593(11) 0.0304(4) Uani 1 1 d . . . . .
H9 H 0.4063 0.2427 0.4338 0.036 Uiso 1 1 calc R . . . .
C10 C 0.1719(3) 0.13748(8) 0.35260(10) 0.0276(3) Uani 1 1 d . . . . .
H10A H 0.0180 0.1158 0.3756 0.033 Uiso 1 1 calc R . . . .
H10B H 0.1124 0.1822 0.3353 0.033 Uiso 1 1 calc R . . . .
C11 C 0.1930(3) 0.02654(7) 0.16706(9) 0.0238(3) Uani 1 1 d . . . . .
C12 C 0.0839(3) -0.02961(7) 0.12641(10) 0.0259(3) Uani 1 1 d . . . . .
H12 H 0.1346 -0.0421 0.0736 0.031 Uiso 1 1 calc R . . . .
C13 C -0.1795(3) -0.04706(7) 0.24760(10) 0.0249(3) Uani 1 1 d . . . . .
C14 C -0.4879(3) -0.14231(8) 0.24871(11) 0.0334(4) Uani 1 1 d . . . . .
H14 H -0.6157 -0.1670 0.2753 0.040 Uiso 1 1 calc R . . . .
C15 C -0.4134(3) -0.16338(8) 0.16943(11) 0.0338(4) Uani 1 1 d . . . . .
H15 H -0.4902 -0.2022 0.1443 0.041 Uiso 1 1 calc R . . . .
C16 C 0.3845(3) 0.07861(7) 0.14887(10) 0.0248(3) Uani 1 1 d . . . . .
C17 C 0.5382(3) 0.09083(8) 0.08152(10) 0.0286(3) Uani 1 1 d . . . . .
H17 H 0.5289 0.0616 0.0354 0.034 Uiso 1 1 calc R . . . .
C18 C -0.2294(3) -0.12719(8) 0.12942(11) 0.0302(4) Uani 1 1 d . . . . .
H18 H -0.1829 -0.1415 0.0769 0.036 Uiso 1 1 calc R . . . .
C19 C -0.3732(3) -0.08565(8) 0.28707(10) 0.0286(3) Uani 1 1 d . . . . .
H19 H -0.4233 -0.0724 0.3396 0.034 Uiso 1 1 calc R . . . .
C20 C 0.8501(3) 0.15354(9) 0.55449(10) 0.0327(4) Uani 1 1 d . . . . .
H20 H 0.9955 0.1572 0.5985 0.039 Uiso 1 1 calc R . . . .
C21 C 0.7704(3) 0.09138(8) 0.52178(11) 0.0330(4) Uani 1 1 d . . . . .
H21 H 0.8624 0.0532 0.5438 0.040 Uiso 1 1 calc R . . . .
C22 C 0.7170(3) 0.19129(8) 0.15226(11) 0.0317(4) Uani 1 1 d . . . . .
H22 H 0.8300 0.2289 0.1525 0.038 Uiso 1 1 calc R . . . .
C23 C 0.7134(3) 0.21018(8) 0.52169(11) 0.0337(4) Uani 1 1 d . . . . .
H23 H 0.7662 0.2520 0.5436 0.040 Uiso 1 1 calc R . . . .
C24 C 0.7054(3) 0.14709(8) 0.08397(11) 0.0315(4) Uani 1 1 d . . . . .
H24 H 0.8107 0.1554 0.0395 0.038 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 C2 1.3815(18) . ?
N1 C8 1.388(2) . ?
N1 C10 1.448(2) . ?
C2 N3 1.3150(19) . ?
C2 C11 1.433(2) . ?
N3 C13 1.3690(19) . ?
C4 C5 1.389(2) . ?
C4 C9 1.385(2) . ?
C4 C10 1.517(2) . ?
C5 C21 1.393(2) . ?
C6 C8 1.394(2) . ?
C6 C22 1.391(2) . ?
C7 C12 1.411(2) . ?
C7 C13 1.429(2) . ?
C7 C18 1.418(2) . ?
C8 C16 1.409(2) . ?
C9 C23 1.388(2) . ?
C11 C12 1.368(2) . ?
C11 C16 1.447(2) . ?
C13 C19 1.416(2) . ?
C14 C15 1.407(3) . ?
C14 C19 1.371(2) . ?
C15 C18 1.361(2) . ?
C16 C17 1.390(2) . ?
C17 C24 1.385(2) . ?
C20 C21 1.384(2) . ?
C20 C23 1.382(2) . ?
C22 C24 1.390(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
C2 N1 C8 108.72(12) . . ?
C2 N1 C10 125.04(13) . . ?
C8 N1 C10 125.64(12) . . ?
N1 C2 C11 108.72(13) . . ?
N3 C2 N1 124.11(14) . . ?
N3 C2 C11 127.17(13) . . ?
C2 N3 C13 114.73(13) . . ?
C5 C4 C10 121.04(13) . . ?
C9 C4 C5 118.99(14) . . ?
C9 C4 C10 119.96(13) . . ?
C4 C5 C21 120.27(14) . . ?
C22 C6 C8 117.32(15) . . ?
C12 C7 C13 119.03(13) . . ?
C12 C7 C18 122.31(15) . . ?
C18 C7 C13 118.66(14) . . ?
N1 C8 C6 128.82(14) . . ?
N1 C8 C16 109.70(13) . . ?
C6 C8 C16 121.47(14) . . ?
C4 C9 C23 120.95(14) . . ?
N1 C10 C4 114.22(12) . . ?
C2 C11 C16 106.46(13) . . ?
C12 C11 C2 117.50(13) . . ?
C12 C11 C16 136.03(14) . . ?
C11 C12 C7 118.39(14) . . ?
N3 C13 C7 123.17(13) . . ?
N3 C13 C19 118.18(14) . . ?
C19 C13 C7 118.65(14) . . ?
C19 C14 C15 120.42(15) . . ?
C18 C15 C14 120.30(15) . . ?
C8 C16 C11 106.39(13) . . ?
C17 C16 C8 119.72(13) . . ?
C17 C16 C11 133.89(14) . . ?
C24 C17 C16 119.14(15) . . ?
C15 C18 C7 121.15(16) . . ?
C14 C19 C13 120.80(16) . . ?
C23 C20 C21 119.90(15) . . ?
C20 C21 C5 120.08(15) . . ?
C24 C22 C6 121.76(14) . . ?
C20 C23 C9 119.81(15) . . ?
C17 C24 C22 120.56(15) . . ?

_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 1.246
_oxdiff_exptl_absorpt_empirical_full_min 0.563
