# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_exp_5458
_audit_block_doi                 10.5517/ccdc.csd.cc1zx0yv
_database_code_depnum_ccdc_archive 'CCDC 1844188'
_audit_update_record             
;
2018-05-19 deposited with the CCDC.
2018-07-04 downloaded from the CCDC.
;
_audit_creation_date             2018-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_chemical_formula_moiety         'C22 H16 N4'
_chemical_formula_sum            'C22 H16 N4'
_chemical_formula_weight         336.40
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.8069(10)
_cell_length_b                   9.7467(7)
_cell_length_c                   15.4870(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.555(7)
_cell_angle_gamma                90
_cell_volume                     1739.6(2)
_exptl_crystal_description       block
_cell_measurement_temperature    298
_diffrn_ambient_temperature      298
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1744
_cell_measurement_theta_max      25.8630
_cell_measurement_theta_min      4.0710
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2843
_exptl_crystal_F_000             704.2498
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8036
_diffrn_reflns_theta_full        24.9917
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.54
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.9971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  73.00   1.00    7.50    --   15.65  57.00   0.00   74
  2  ω    -19.00   7.00   1.00    7.50    --  -16.28 -99.00   0.00   26
  3  ω    -53.00  35.00   1.00    7.50    --   15.65 -38.00-150.00   88
  4  ω     -5.00  23.00   1.00    7.50    --  -16.28 -99.00-180.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0512310000
_diffrn_orient_matrix_UB_12      -0.0391450000
_diffrn_orient_matrix_UB_13      -0.0024702000
_diffrn_orient_matrix_UB_21      -0.0330430000
_diffrn_orient_matrix_UB_22      0.0613110000
_diffrn_orient_matrix_UB_23      -0.0036828000
_diffrn_orient_matrix_UB_31      -0.0081614000
_diffrn_orient_matrix_UB_32      -0.0027478000
_diffrn_orient_matrix_UB_33      -0.0467368000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -14
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2070
_reflns_number_total             3058
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.3131
_refine_diff_density_min         -0.3652
_refine_diff_density_rms         0.0940
_refine_ls_d_res_high            0.8411
_refine_ls_d_res_low             5.7623
_refine_ls_goodness_of_fit_ref   0.9260
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3058
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0569
_refine_ls_restrained_S_all      0.9260
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1316
_refine_ls_wR_factor_ref         0.1572
_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:
 C00I(H00b,H00c)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00M(H00M), C00L(H00L), C00K(H00K), C00D(H00D), C00N(H00N),
 C00Q(H00Q), C00O(H00O), C00P(H00P), C00H(H00H), C00A(H00A), C00F(H00F),
 C00J(H00J), C00G(H00G)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
N001 N 0.78978(16) 0.24671(17) 0.42630(11) 0.0481(5) Uani 1.000000 .
N002 N 0.87882(16) 0.34632(19) 0.33744(10) 0.0521(5) Uani 1.000000 .
N003 N 0.84467(18) 0.22635(19) 0.35954(12) 0.0591(5) Uani 1.000000 .
C004 C 0.84606(17) 0.4438(2) 0.38952(11) 0.0399(5) Uani 1.000000 .
C005 C 0.87810(15) 0.5888(2) 0.38540(11) 0.0389(5) Uani 1.000000 .
C006 C 0.73882(17) 0.4364(2) 0.51883(11) 0.0405(5) Uani 1.000000 .
C007 C 0.88587(17) 0.6533(2) 0.30582(12) 0.0431(5) Uani 1.000000 .
C008 C 0.78933(17) 0.3805(2) 0.44755(12) 0.0403(5) Uani 1.000000 .
N009 N 0.83591(19) 0.5412(3) 0.15203(13) 0.0787(7) Uani 1.000000 .
C00A C 0.90375(17) 0.6669(2) 0.46192(12) 0.0456(5) Uani 1.000000 .
C00B C 0.85899(19) 0.5851(2) 0.22185(14) 0.0525(6) Uani 1.000000 .
C00C C 0.63499(19) 0.0679(2) 0.40693(13) 0.0489(6) Uani 1.000000 .
C00D C 0.7765(2) 0.3929(2) 0.60538(12) 0.0539(6) Uani 1.000000 .
C00E C 0.65923(19) 0.5407(2) 0.50131(14) 0.0536(6) Uani 1.000000 .
C00F C 0.93201(19) 0.8027(2) 0.45997(15) 0.0559(6) Uani 1.000000 .
C00G C 0.9181(2) 0.7898(2) 0.30504(15) 0.0569(6) Uani 1.000000 .
C00H C 0.5608(2) 0.1399(3) 0.34213(14) 0.0604(6) Uani 1.000000 .
C00I C 0.7427(2) 0.1282(2) 0.46409(14) 0.0599(6) Uani 1.000000 .
C00J C 0.9396(2) 0.8641(3) 0.38204(16) 0.0645(7) Uani 1.000000 .
C00K C 0.7329(2) 0.4529(3) 0.67178(14) 0.0675(7) Uani 1.000000 .
C00L C 0.6541(2) 0.5560(3) 0.65322(16) 0.0701(7) Uani 1.000000 .
C00M C 0.6167(2) 0.6005(3) 0.56848(16) 0.0675(7) Uani 1.000000 .
C00N C 0.6067(2) -0.0647(3) 0.42349(17) 0.0708(7) Uani 1.000000 .
C00O C 0.4326(2) -0.0503(3) 0.31382(19) 0.0779(8) Uani 1.000000 .
C00P C 0.4596(2) 0.0797(3) 0.29640(16) 0.0749(8) Uani 1.000000 .
C00Q C 0.5062(2) -0.1237(3) 0.3771(2) 0.0829(8) Uani 1.000000 .
H00E H 0.63363(19) 0.5714(2) 0.44350(14) 0.0644(7) Uiso 1.000000 R
H00M H 0.5626(2) 0.6711(3) 0.55593(16) 0.0810(8) Uiso 1.000000 R
H00L H 0.6255(2) 0.5964(3) 0.69856(16) 0.0841(9) Uiso 1.000000 R
H00K H 0.7576(2) 0.4226(3) 0.72976(14) 0.0810(9) Uiso 1.000000 R
H00D H 0.8314(2) 0.3232(2) 0.61869(12) 0.0647(7) Uiso 1.000000 R
H00N H 0.6564(2) -0.1153(3) 0.46677(17) 0.0849(9) Uiso 1.000000 R
H00Q H 0.4883(2) -0.2138(3) 0.3888(2) 0.0995(10) Uiso 1.000000 R
H00O H 0.3640(2) -0.0897(3) 0.28280(19) 0.0934(10) Uiso 1.000000 R
H00P H 0.4095(2) 0.1295(3) 0.25299(16) 0.0898(9) Uiso 1.000000 R
H00H H 0.5787(2) 0.2294(3) 0.32906(14) 0.0725(8) Uiso 1.000000 R
H00A H 0.90169(17) 0.6260(2) 0.51582(12) 0.0547(6) Uiso 1.000000 R
H00F H 0.94619(19) 0.8536(2) 0.51198(15) 0.0671(7) Uiso 1.000000 R
H00J H 0.9593(2) 0.9564(3) 0.38127(16) 0.0774(8) Uiso 1.000000 R
H00G H 0.9252(2) 0.8310(2) 0.25233(15) 0.0683(7) Uiso 1.000000 R
H00b H 0.8019(2) 0.0575(2) 0.47617(14) 0.0718(8) Uiso 1.000000 R
H00c H 0.7254(2) 0.1550(2) 0.52018(14) 0.0718(8) Uiso 1.000000 R


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
N001 N003 1.349(3) . ?
N001 C008 1.345(2) . ?
N001 C00I 1.459(3) . ?
N002 N003 1.307(2) . ?
N002 C004 1.356(2) . ?
C004 C005 1.468(3) . ?
C004 C008 1.378(3) . ?
C005 C007 1.405(3) . ?
C005 C00A 1.385(3) . ?
C006 C008 1.469(3) . ?
C006 C00D 1.384(3) . ?
C006 C00E 1.371(3) . ?
C007 C00B 1.433(3) . ?
C007 C00G 1.384(3) . ?
N009 C00B 1.140(2) . ?
C00A C00F 1.367(3) . ?
C00A H00A 0.9300 . ?
C00C C00H 1.374(3) . ?
C00C C00I 1.502(3) . ?
C00C C00N 1.372(3) . ?
C00D C00K 1.377(3) . ?
C00D H00D 0.9300 . ?
C00E C00M 1.379(3) . ?
C00E H00E 0.9300 . ?
C00F C00J 1.367(3) . ?
C00F H00F 0.9300 . ?
C00G C00J 1.371(3) . ?
C00G H00G 0.9300 . ?
C00H C00P 1.380(3) . ?
C00H H00H 0.9300 . ?
C00I H00b 0.9700 . ?
C00I H00c 0.9700 . ?
C00J H00J 0.9300 . ?
C00K C00L 1.357(4) . ?
C00K H00K 0.9300 . ?
C00L C00M 1.361(3) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00N C00Q 1.373(3) . ?
C00N H00N 0.9300 . ?
C00O C00P 1.348(4) . ?
C00O C00Q 1.362(4) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00Q H00Q 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
C008 N001 N003 110.99(17) . . ?
C00I N001 N003 118.66(17) . . ?
C00I N001 C008 130.35(18) . . ?
C004 N002 N003 109.10(17) . . ?
N002 N003 N001 107.23(16) . . ?
C005 C004 N002 122.63(17) . . ?
C008 C004 N002 108.43(18) . . ?
C008 C004 C005 128.74(17) . . ?
C007 C005 C004 122.42(17) . . ?
C00A C005 C004 120.16(17) . . ?
C00A C005 C007 117.42(19) . . ?
C00D C006 C008 121.11(19) . . ?
C00E C006 C008 119.94(17) . . ?
C00E C006 C00D 118.76(19) . . ?
C00B C007 C005 122.98(19) . . ?
C00G C007 C005 120.58(18) . . ?
C00G C007 C00B 116.43(19) . . ?
C004 C008 N001 104.25(17) . . ?
C006 C008 N001 124.54(18) . . ?
C006 C008 C004 131.20(19) . . ?
C00F C00A C005 121.48(19) . . ?
H00A C00A C005 119.26(12) . . ?
H00A C00A C00F 119.26(12) . . ?
N009 C00B C007 174.4(3) . . ?
C00I C00C C00H 123.7(2) . . ?
C00N C00C C00H 118.4(2) . . ?
C00N C00C C00I 117.85(19) . . ?
C00K C00D C006 120.0(2) . . ?
H00D C00D C006 120.02(13) . . ?
H00D C00D C00K 120.02(15) . . ?
C00M C00E C006 120.7(2) . . ?
H00E C00E C006 119.64(11) . . ?
H00E C00E C00M 119.64(14) . . ?
C00J C00F C00A 120.4(2) . . ?
H00F C00F C00A 119.78(12) . . ?
H00F C00F C00J 119.78(14) . . ?
C00J C00G C007 120.0(2) . . ?
H00G C00G C007 120.02(12) . . ?
H00G C00G C00J 120.02(14) . . ?
C00P C00H C00C 120.1(2) . . ?
H00H C00H C00C 119.96(14) . . ?
H00H C00H C00P 119.96(16) . . ?
C00C C00I N001 114.90(17) . . ?
H00b C00I N001 108.54(12) . . ?
H00b C00I C00C 108.54(12) . . ?
H00c C00I N001 108.54(12) . . ?
H00c C00I C00C 108.54(12) . . ?
H00c C00I H00b 107.5 . . ?
C00G C00J C00F 120.1(2) . . ?
H00J C00J C00F 119.97(14) . . ?
H00J C00J C00G 119.97(14) . . ?
C00L C00K C00D 120.5(2) . . ?
H00K C00K C00D 119.77(15) . . ?
H00K C00K C00L 119.77(13) . . ?
C00M C00L C00K 120.3(2) . . ?
H00L C00L C00K 119.87(13) . . ?
H00L C00L C00M 119.87(15) . . ?
C00L C00M C00E 119.8(2) . . ?
H00M C00M C00E 120.09(14) . . ?
H00M C00M C00L 120.09(15) . . ?
C00Q C00N C00C 120.9(2) . . ?
H00N C00N C00C 119.53(13) . . ?
H00N C00N C00Q 119.53(17) . . ?
C00Q C00O C00P 119.7(3) . . ?
H00O C00O C00P 120.14(16) . . ?
H00O C00O C00Q 120.14(17) . . ?
C00O C00P C00H 120.9(2) . . ?
H00P C00P C00H 119.57(16) . . ?
H00P C00P C00O 119.57(16) . . ?
C00O C00Q C00N 120.0(3) . . ?
H00Q C00Q C00N 120.00(17) . . ?
H00Q C00Q C00O 120.00(17) . . ?


_olex2_date_sample_data_collection 2018-05-10
_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 2.104
_oxdiff_exptl_absorpt_empirical_full_min 0.578
