# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_mPmPCZ
_database_code_depnum_ccdc_archive 'CCDC 2255989'
loop_
_audit_author_name
_audit_author_address
'Xu Qiu'
;Shandong University of Science and Technology
China
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-09-05 downloaded from the CCDC.
;
_audit_creation_date             2023-02-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H28 N4'
_chemical_formula_sum            'C44 H28 N4'
_chemical_formula_weight         612.70
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2039(3)
_cell_length_b                   9.4040(4)
_cell_length_c                   18.0371(4)
_cell_angle_alpha                96.637(3)
_cell_angle_beta                 90.417(2)
_cell_angle_gamma                98.521(3)
_cell_volume                     1533.12(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6710
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6950
_cell_measurement_theta_min      4.7490
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13822
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         4.788
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00   4.00   0.50    0.50    --   -1.00 -72.00 120.00  186
  2  ω    -85.00 -39.00   0.50    0.50    --   -1.00 -72.00 -30.00   92
  3  ω    -29.00  11.00   0.50    0.50    --   -1.00 -72.00 -30.00   80
  4  ω    -80.00 -41.00   0.50    0.50    --    1.00 -38.00 150.00   78
  5  ω    -37.00  13.00   0.50    0.50    --    1.00 -38.00 150.00  100
  6  ω    -34.00   8.00   0.50    0.50    --    1.00 -19.00-180.00   84
  7  ω   -113.00 -64.00   0.50    0.59    -- -100.10  72.00  90.00   98
  8  ω   -114.00 -21.00   0.50    0.59    -- -100.10  72.00 -90.00  186
  9  ω   -109.00 -13.00   0.50    0.59    -- -100.10  72.00 150.00  192
 10  ω   -189.00-135.00   0.50    0.59    -- -100.10 -19.00 120.00  108
 11  ω   -114.00 -88.00   0.50    0.59    -- -100.10 -19.00 120.00   52
 12  ω   -109.00 -69.00   0.50    0.59    -- -100.10  72.00-150.00   80
 13  ω   -107.00 -79.00   0.50    0.59    -- -100.10  72.00  30.00   56
 14  ω    -69.00 -22.00   0.50    0.59    -- -100.10  72.00  30.00   94
 15  ω   -110.00 -51.00   0.50    0.59    -- -100.10  72.00   0.00  118
 16  ω    -55.00 -26.00   0.50    0.59    -- -100.10  57.00 150.00   58
 17  ω   -113.00 -65.00   0.50    0.59    -- -100.10  57.00 150.00   96
 18  ω   -105.00 -30.00   0.50    0.59    -- -100.10  57.00 -90.00  150
 19  ω   -141.00 -95.00   0.50    0.59    -- -100.10 -19.00  30.00   92
 20  ω   -185.00-151.00   0.50    0.59    -- -100.10 -19.00  30.00   68
 21  ω   -112.00 -15.00   0.50    0.59    -- -100.10  19.00  60.00  194
 22  ω   -189.00 -88.00   0.50    0.59    -- -100.10 -19.00  60.00  202
 23  ω   -141.00-102.00   0.50    0.59    -- -100.10 -19.00 -60.00   78
 24  ω    -93.00 -67.00   0.50    0.59    -- -100.10  72.00 -60.00   52
 25  ω    -93.00 -67.00   0.50    0.59    -- -100.10  72.00-120.00   52
 26  ω   -101.00 -14.00   0.50    0.59    -- -100.10  72.00 -22.01  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0013618000
_diffrn_orient_matrix_UB_12      -0.0404566000
_diffrn_orient_matrix_UB_13      -0.0852675000
_diffrn_orient_matrix_UB_21      -0.0783650000
_diffrn_orient_matrix_UB_22      0.1303373000
_diffrn_orient_matrix_UB_23      -0.0106081000
_diffrn_orient_matrix_UB_31      0.1500670000
_diffrn_orient_matrix_UB_32      0.0959271000
_diffrn_orient_matrix_UB_33      -0.0039035000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4703
_reflns_number_total             5376
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         5376
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.046
_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)+(0.0821P)²+0.4248P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1370
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N009-C010 \\sim N0-C2
 with sigma of 0.02
 N009-C00O \\sim N0-C00O
 with sigma of 0.02
 C00L-C00P \\sim C00L-C1
 with sigma of 0.04
 C010-C00L \\sim C2-C00L
 with sigma of 0.02
 C010-C00O \\sim C2-C00O
 with sigma of 0.04
 C00L-C019 \\sim C00L-C0
 with sigma of 0.02
 C019-C00P \\sim C0-C1
 with sigma of 0.02
 C019-C00O \\sim C0-C00O
 with sigma of 0.04
 C00P-C00O \\sim C1-C00O
 with sigma of 0.02
 N009-C00L \\sim N0-C00L
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C2) = Uanis(C010)
Uanis(N009) = Uanis(N0)
Uanis(C1) = Uanis(C00P)
Uanis(C0) = Uanis(C019)
4. Others
 Sof(N0)=Sof(C1)=Sof(H1)=Sof(C0)=Sof(H0)=Sof(C2)=Sof(H2)=1-FVAR(1)
 Sof(N009)=Sof(C010)=Sof(H010)=Sof(C019)=Sof(H019)=Sof(C00P)=Sof(H00P)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C010(H010), C019(H019), C00P(H00P), C00A(H00A), C00B(H00B), C00E(H00E),
 C00J(H00J), C00M(H00M), C00N(H00N), C00S(H00S), C00T(H00T), C00U(H00U),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C011(H011),
 C012(H012), C013(H013), C014(H014), C015(H015), C016(H016), C017(H017),
 C018(H018), C01A(H01A), C01B(H01B), C01C(H01C), C1(H1), C0(H0), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N001 N 0.61642(14) 0.69344(13) 0.58987(7) 0.0274(3) Uani 1 1 d . . . . .
N002 N 0.25062(16) 0.92526(15) 0.10256(7) 0.0339(3) Uani 1 1 d . . . . .
N003 N 0.37513(14) 0.62862(14) 0.56617(7) 0.0311(3) Uani 1 1 d . . . . .
C004 C 0.76843(16) 0.74630(16) 0.57972(8) 0.0276(3) Uani 1 1 d . . . . .
C005 C 0.49805(17) 0.69988(16) 0.54338(9) 0.0287(3) Uani 1 1 d . . . . .
C006 C 0.2619(2) 0.81015(17) 0.04807(8) 0.0350(4) Uani 1 1 d . . . . .
C007 C 0.10423(19) 0.94471(18) 0.10687(9) 0.0354(4) Uani 1 1 d . . . . .
C008 C 0.0204(2) 0.84416(19) 0.05342(10) 0.0402(4) Uani 1 1 d . . . . .
N009 N 0.3686(7) 0.7929(6) 0.3642(3) 0.0313(10) Uani 0.526(9) 1 d D . P A 1
C010 C 0.3777(8) 0.7272(7) 0.4265(4) 0.0290(10) Uani 0.526(9) 1 d D . P A 1
H010 H 0.3041 0.6539 0.4372 0.035 Uiso 0.526(9) 1 calc R U P A 1
C00L C 0.50205(17) 0.77239(16) 0.47529(9) 0.0294(3) Uani 1 1 d D . . . .
C019 C 0.6006(6) 0.8828(7) 0.4597(3) 0.0326(11) Uani 0.526(9) 1 d D . P A 1
H019 H 0.6787 0.9169 0.4932 0.039 Uiso 0.526(9) 1 calc R U P A 1
C00P C 0.5913(6) 0.9469(8) 0.3973(3) 0.0307(10) Uani 0.526(9) 1 d D . P A 1
H00P H 0.6619 1.0251 0.3896 0.037 Uiso 0.526(9) 1 calc R U P A 1
C00O C 0.48526(16) 0.90246(16) 0.34636(8) 0.0277(3) Uani 1 1 d D . . . .
C00A C 0.37064(17) 0.91868(16) 0.22193(8) 0.0290(3) Uani 1 1 d . . . . .
H00A H 0.3061 0.8349 0.2275 0.035 Uiso 1 1 calc R U . . .
C00B C 0.57051(17) 1.10134(17) 0.26775(9) 0.0319(4) Uani 1 1 d . . . . .
H00B H 0.6421 1.1403 0.3041 0.038 Uiso 1 1 calc R U . . .
C00C C 0.36101(18) 0.98650(17) 0.15846(8) 0.0303(3) Uani 1 1 d . . . . .
C00D C 0.56231(17) 0.60829(16) 0.64481(8) 0.0275(3) Uani 1 1 d . . . . .
C00E C 0.84976(19) 0.66118(18) 0.53478(10) 0.0378(4) Uani 1 1 d . . . . .
H00E H 0.8051 0.5734 0.5097 0.045 Uiso 1 1 calc R U . . .
C00F C 0.47625(16) 0.97462(16) 0.27768(8) 0.0274(3) Uani 1 1 d . . . . .
C00G C 0.41463(17) 0.57178(16) 0.62909(8) 0.0297(3) Uani 1 1 d . . . . .
C00H C 0.31991(18) 0.48164(17) 0.67349(9) 0.0321(4) Uani 1 1 d . . . . .
C00I C 0.38609(19) 0.42984(17) 0.73410(9) 0.0332(4) Uani 1 1 d . . . . .
C00J C 0.55880(19) 1.16953(18) 0.20464(10) 0.0373(4) Uani 1 1 d . . . . .
H00J H 0.6219 1.2543 0.1991 0.045 Uiso 1 1 calc R U . . .
C00K C 0.1211(2) 0.75745(18) 0.01649(9) 0.0404(4) Uani 1 1 d . . . . .
C00M C 0.3858(2) 0.75042(19) 0.02525(9) 0.0410(4) Uani 1 1 d . . . . .
H00M H 0.4781 0.7871 0.0464 0.049 Uiso 1 1 calc R U . . .
C00N C 0.78425(18) 0.60180(18) 0.72682(9) 0.0340(4) Uani 1 1 d . . . . .
H00N H 0.8458 0.6551 0.6960 0.041 Uiso 1 1 calc R U . . .
C00Q C 0.63431(18) 0.56513(16) 0.70786(8) 0.0298(3) Uani 1 1 d . . . . .
C00R C 0.54145(18) 0.47758(17) 0.75332(9) 0.0320(4) Uani 1 1 d . . . . .
C00S C 0.8421(2) 0.56043(19) 0.79016(10) 0.0402(4) Uani 1 1 d . . . . .
H00S H 0.9419 0.5858 0.8018 0.048 Uiso 1 1 calc R U . . .
C00T C 0.0428(2) 1.0468(2) 0.15385(11) 0.0435(4) Uani 1 1 d . . . . .
H00T H 0.0998 1.1115 0.1893 0.052 Uiso 1 1 calc R U . . .
C00U C 0.45377(19) 1.11261(18) 0.14936(9) 0.0361(4) Uani 1 1 d . . . . .
H00U H 0.4459 1.1586 0.1069 0.043 Uiso 1 1 calc R U . . .
C00V C 0.6052(2) 0.44079(18) 0.81836(9) 0.0376(4) Uani 1 1 d . . . . .
H00V H 0.5459 0.3874 0.8500 0.045 Uiso 1 1 calc R U . . .
C00W C 0.83258(19) 0.87893(18) 0.61615(10) 0.0367(4) Uani 1 1 d . . . . .
H00W H 0.7767 0.9366 0.6458 0.044 Uiso 1 1 calc R U . . .
C00X C 0.0846(2) 0.3476(2) 0.69805(11) 0.0444(4) Uani 1 1 d . . . . .
H00X H -0.0154 0.3218 0.6871 0.053 Uiso 1 1 calc R U . . .
C00Y C 0.7514(2) 0.48081(19) 0.83667(10) 0.0422(4) Uani 1 1 d . . . . .
H00Y H 0.7899 0.4548 0.8801 0.051 Uiso 1 1 calc R U . . .
C00Z C 0.16889(19) 0.44285(19) 0.65754(10) 0.0391(4) Uani 1 1 d . . . . .
H00Z H 0.1255 0.4817 0.6193 0.047 Uiso 1 1 calc R U . . .
C011 C 0.1056(3) 0.6405(2) -0.03946(10) 0.0533(5) Uani 1 1 d . . . . .
H011 H 0.0138 0.6038 -0.0612 0.064 Uiso 1 1 calc R U . . .
C012 C -0.1304(2) 0.8491(2) 0.04691(12) 0.0523(5) Uani 1 1 d . . . . .
H012 H -0.1888 0.7843 0.0121 0.063 Uiso 1 1 calc R U . . .
C013 C 0.2959(2) 0.33019(18) 0.77316(10) 0.0389(4) Uani 1 1 d . . . . .
H013 H 0.3371 0.2908 0.8118 0.047 Uiso 1 1 calc R U . . .
C014 C 0.9805(2) 0.9240(2) 0.60770(12) 0.0481(5) Uani 1 1 d . . . . .
H014 H 1.0247 1.0129 0.6317 0.058 Uiso 1 1 calc R U . . .
C015 C 0.1495(2) 0.2901(2) 0.75556(10) 0.0445(4) Uani 1 1 d . . . . .
H015 H 0.0930 0.2239 0.7822 0.053 Uiso 1 1 calc R U . . .
C016 C -0.1058(2) 1.0480(2) 0.14559(13) 0.0539(5) Uani 1 1 d . . . . .
H016 H -0.1500 1.1151 0.1761 0.065 Uiso 1 1 calc R U . . .
C017 C 1.0635(2) 0.8380(2) 0.56374(13) 0.0539(5) Uani 1 1 d . . . . .
H017 H 1.1635 0.8684 0.5588 0.065 Uiso 1 1 calc R U . . .
C018 C -0.1914(2) 0.9511(2) 0.09276(14) 0.0584(6) Uani 1 1 d . . . . .
H018 H -0.2914 0.9552 0.0883 0.070 Uiso 1 1 calc R U . . .
C01A C 0.9977(2) 0.7067(2) 0.52717(12) 0.0516(5) Uani 1 1 d . . . . .
H01A H 1.0534 0.6490 0.4974 0.062 Uiso 1 1 calc R U . . .
C01B C 0.3662(3) 0.6334(2) -0.03058(11) 0.0538(5) Uani 1 1 d . . . . .
H01B H 0.4468 0.5905 -0.0470 0.065 Uiso 1 1 calc R U . . .
C01C C 0.2276(3) 0.5799(2) -0.06220(11) 0.0611(6) Uani 1 1 d . . . . .
H01C H 0.2172 0.5016 -0.0994 0.073 Uiso 1 1 calc R U . . .
N0 N 0.6215(5) 0.9221(8) 0.3838(3) 0.0313(10) Uani 0.474(9) 1 d D . P A 2
C1 C 0.3709(10) 0.8312(9) 0.3673(4) 0.0307(10) Uani 0.474(9) 1 d D . P A 2
H1 H 0.2821 0.8245 0.3412 0.037 Uiso 0.474(9) 1 calc R U P A 2
C0 C 0.3804(10) 0.7627(8) 0.4304(4) 0.0326(11) Uani 0.474(9) 1 d D . P A 2
H0 H 0.2960 0.7045 0.4435 0.039 Uiso 0.474(9) 1 calc R U P A 2
C2 C 0.6329(5) 0.8545(7) 0.4451(3) 0.0290(10) Uani 0.474(9) 1 d D . P A 2
H2 H 0.7242 0.8596 0.4686 0.035 Uiso 0.474(9) 1 calc R U P A 2


_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
N001 C004 1.434(2) . ?
N001 C005 1.383(2) . ?
N001 C00D 1.3941(19) . ?
N002 C006 1.392(2) . ?
N002 C007 1.388(2) . ?
N002 C00C 1.435(2) . ?
N003 C005 1.321(2) . ?
N003 C00G 1.378(2) . ?
C004 C00E 1.376(2) . ?
C004 C00W 1.387(2) . ?
C005 C00L 1.470(2) . ?
C006 C00K 1.408(3) . ?
C006 C00M 1.388(3) . ?
C007 C008 1.408(2) . ?
C007 C00T 1.393(3) . ?
C008 C00K 1.441(3) . ?
C008 C012 1.400(3) . ?
N009 C010 1.352(7) . ?
N009 C00O 1.439(5) . ?
C010 H010 0.9300 . ?
C010 C00L 1.421(6) . ?
C00L C019 1.331(5) . ?
C00L C0 1.363(7) . ?
C00L C2 1.474(5) . ?
C019 H019 0.9300 . ?
C019 C00P 1.346(7) . ?
C00P H00P 0.9300 . ?
C00P C00O 1.322(5) . ?
C00O C00F 1.487(2) . ?
C00O N0 1.398(4) . ?
C00O C1 1.247(8) . ?
C00A H00A 0.9300 . ?
C00A C00C 1.382(2) . ?
C00A C00F 1.395(2) . ?
C00B H00B 0.9300 . ?
C00B C00F 1.397(2) . ?
C00B C00J 1.381(2) . ?
C00C C00U 1.382(2) . ?
C00D C00G 1.371(2) . ?
C00D C00Q 1.440(2) . ?
C00E H00E 0.9300 . ?
C00E C01A 1.378(3) . ?
C00G C00H 1.438(2) . ?
C00H C00I 1.416(2) . ?
C00H C00Z 1.403(2) . ?
C00I C00R 1.460(2) . ?
C00I C013 1.412(2) . ?
C00J H00J 0.9300 . ?
C00J C00U 1.387(2) . ?
C00K C011 1.394(3) . ?
C00M H00M 0.9300 . ?
C00M C01B 1.393(3) . ?
C00N H00N 0.9300 . ?
C00N C00Q 1.402(2) . ?
C00N C00S 1.377(2) . ?
C00Q C00R 1.428(2) . ?
C00R C00V 1.409(2) . ?
C00S H00S 0.9300 . ?
C00S C00Y 1.390(3) . ?
C00T H00T 0.9300 . ?
C00T C016 1.377(3) . ?
C00U H00U 0.9300 . ?
C00V H00V 0.9300 . ?
C00V C00Y 1.370(3) . ?
C00W H00W 0.9300 . ?
C00W C014 1.380(3) . ?
C00X H00X 0.9300 . ?
C00X C00Z 1.375(2) . ?
C00X C015 1.394(3) . ?
C00Y H00Y 0.9300 . ?
C00Z H00Z 0.9300 . ?
C011 H011 0.9300 . ?
C011 C01C 1.377(3) . ?
C012 H012 0.9300 . ?
C012 C018 1.379(3) . ?
C013 H013 0.9300 . ?
C013 C015 1.369(3) . ?
C014 H014 0.9300 . ?
C014 C017 1.382(3) . ?
C015 H015 0.9300 . ?
C016 H016 0.9300 . ?
C016 C018 1.390(3) . ?
C017 H017 0.9300 . ?
C017 C01A 1.382(3) . ?
C018 H018 0.9300 . ?
C01A H01A 0.9300 . ?
C01B H01B 0.9300 . ?
C01B C01C 1.393(3) . ?
C01C H01C 0.9300 . ?
N0 C2 1.349(7) . ?
C1 H1 0.9300 . ?
C1 C0 1.380(9) . ?
C0 H0 0.9300 . ?
C2 H2 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
C005 N001 C004 127.83(13) . . ?
C005 N001 C00D 106.31(12) . . ?
C00D N001 C004 125.41(12) . . ?
C006 N002 C00C 125.40(14) . . ?
C007 N002 C006 108.48(14) . . ?
C007 N002 C00C 124.06(13) . . ?
C005 N003 C00G 105.35(13) . . ?
C00E C004 N001 118.69(14) . . ?
C00E C004 C00W 120.89(15) . . ?
C00W C004 N001 120.40(14) . . ?
N001 C005 C00L 126.39(14) . . ?
N003 C005 N001 111.79(13) . . ?
N003 C005 C00L 121.81(14) . . ?
N002 C006 C00K 108.61(16) . . ?
C00M C006 N002 128.98(16) . . ?
C00M C006 C00K 122.41(16) . . ?
N002 C007 C008 109.25(15) . . ?
N002 C007 C00T 128.09(16) . . ?
C00T C007 C008 122.65(17) . . ?
C007 C008 C00K 106.42(16) . . ?
C012 C008 C007 118.26(18) . . ?
C012 C008 C00K 135.31(18) . . ?
C010 N009 C00O 120.5(4) . . ?
N009 C010 H010 120.7 . . ?
N009 C010 C00L 118.6(4) . . ?
C00L C010 H010 120.7 . . ?
C005 C00L C2 126.1(2) . . ?
C010 C00L C005 114.5(3) . . ?
C019 C00L C005 126.6(2) . . ?
C019 C00L C010 118.5(3) . . ?
C0 C00L C005 121.5(3) . . ?
C0 C00L C2 112.4(4) . . ?
C00L C019 H019 118.8 . . ?
C00L C019 C00P 122.4(4) . . ?
C00P C019 H019 118.8 . . ?
C019 C00P H00P 118.9 . . ?
C00O C00P C019 122.2(5) . . ?
C00O C00P H00P 118.9 . . ?
N009 C00O C00F 120.8(2) . . ?
C00P C00O N009 117.2(3) . . ?
C00P C00O C00F 121.6(3) . . ?
N0 C00O C00F 117.3(2) . . ?
C1 C00O C00F 118.0(3) . . ?
C1 C00O N0 124.6(3) . . ?
C00C C00A H00A 119.7 . . ?
C00C C00A C00F 120.66(14) . . ?
C00F C00A H00A 119.7 . . ?
C00F C00B H00B 119.6 . . ?
C00J C00B H00B 119.6 . . ?
C00J C00B C00F 120.83(15) . . ?
C00A C00C N002 118.78(14) . . ?
C00A C00C C00U 120.87(15) . . ?
C00U C00C N002 120.33(14) . . ?
N001 C00D C00Q 131.18(14) . . ?
C00G C00D N001 105.36(13) . . ?
C00G C00D C00Q 123.43(14) . . ?
C004 C00E H00E 120.2 . . ?
C004 C00E C01A 119.63(16) . . ?
C01A C00E H00E 120.2 . . ?
C00A C00F C00O 120.58(13) . . ?
C00A C00F C00B 118.13(14) . . ?
C00B C00F C00O 121.28(14) . . ?
N003 C00G C00H 126.82(15) . . ?
C00D C00G N003 111.17(14) . . ?
C00D C00G C00H 121.98(15) . . ?
C00I C00H C00G 117.07(15) . . ?
C00Z C00H C00G 122.40(16) . . ?
C00Z C00H C00I 120.52(15) . . ?
C00H C00I C00R 120.32(15) . . ?
C013 C00I C00H 117.00(16) . . ?
C013 C00I C00R 122.68(16) . . ?
C00B C00J H00J 119.7 . . ?
C00B C00J C00U 120.57(15) . . ?
C00U C00J H00J 119.7 . . ?
C006 C00K C008 107.22(15) . . ?
C011 C00K C006 118.72(19) . . ?
C011 C00K C008 134.06(19) . . ?
C006 C00M H00M 121.3 . . ?
C006 C00M C01B 117.36(19) . . ?
C01B C00M H00M 121.3 . . ?
C00Q C00N H00N 119.4 . . ?
C00S C00N H00N 119.4 . . ?
C00S C00N C00Q 121.23(16) . . ?
C00N C00Q C00D 125.44(15) . . ?
C00N C00Q C00R 119.22(15) . . ?
C00R C00Q C00D 115.34(14) . . ?
C00Q C00R C00I 121.58(15) . . ?
C00V C00R C00I 121.15(15) . . ?
C00V C00R C00Q 117.26(15) . . ?
C00N C00S H00S 120.0 . . ?
C00N C00S C00Y 119.99(17) . . ?
C00Y C00S H00S 120.0 . . ?
C007 C00T H00T 121.4 . . ?
C016 C00T C007 117.20(19) . . ?
C016 C00T H00T 121.4 . . ?
C00C C00U C00J 118.92(15) . . ?
C00C C00U H00U 120.5 . . ?
C00J C00U H00U 120.5 . . ?
C00R C00V H00V 118.8 . . ?
C00Y C00V C00R 122.35(16) . . ?
C00Y C00V H00V 118.8 . . ?
C004 C00W H00W 120.5 . . ?
C014 C00W C004 119.01(16) . . ?
C014 C00W H00W 120.5 . . ?
C00Z C00X H00X 120.1 . . ?
C00Z C00X C015 119.75(18) . . ?
C015 C00X H00X 120.1 . . ?
C00S C00Y H00Y 120.1 . . ?
C00V C00Y C00S 119.81(16) . . ?
C00V C00Y H00Y 120.1 . . ?
C00H C00Z H00Z 119.8 . . ?
C00X C00Z C00H 120.38(18) . . ?
C00X C00Z H00Z 119.8 . . ?
C00K C011 H011 120.3 . . ?
C01C C011 C00K 119.4(2) . . ?
C01C C011 H011 120.3 . . ?
C008 C012 H012 120.4 . . ?
C018 C012 C008 119.27(19) . . ?
C018 C012 H012 120.4 . . ?
C00I C013 H013 119.1 . . ?
C015 C013 C00I 121.70(17) . . ?
C015 C013 H013 119.1 . . ?
C00W C014 H014 119.8 . . ?
C00W C014 C017 120.44(17) . . ?
C017 C014 H014 119.8 . . ?
C00X C015 H015 119.8 . . ?
C013 C015 C00X 120.50(16) . . ?
C013 C015 H015 119.8 . . ?
C00T C016 H016 119.2 . . ?
C00T C016 C018 121.5(2) . . ?
C018 C016 H016 119.2 . . ?
C014 C017 H017 120.1 . . ?
C01A C017 C014 119.87(17) . . ?
C01A C017 H017 120.1 . . ?
C012 C018 C016 121.08(19) . . ?
C012 C018 H018 119.5 . . ?
C016 C018 H018 119.5 . . ?
C00E C01A C017 120.14(17) . . ?
C00E C01A H01A 119.9 . . ?
C017 C01A H01A 119.9 . . ?
C00M C01B H01B 119.6 . . ?
C00M C01B C01C 120.9(2) . . ?
C01C C01B H01B 119.6 . . ?
C011 C01C C01B 121.29(18) . . ?
C011 C01C H01C 119.4 . . ?
C01B C01C H01C 119.4 . . ?
C2 N0 C00O 118.2(4) . . ?
C00O C1 H1 121.1 . . ?
C00O C1 C0 117.8(6) . . ?
C0 C1 H1 121.1 . . ?
C00L C0 C1 126.0(6) . . ?
C00L C0 H0 117.0 . . ?
C1 C0 H0 117.0 . . ?
C00L C2 H2 119.7 . . ?
N0 C2 C00L 120.6(4) . . ?
N0 C2 H2 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N001 C004 C00E C01A -176.83(17) . . . . ?
N001 C004 C00W C014 177.32(16) . . . . ?
N001 C005 C00L C010 161.9(4) . . . . ?
N001 C005 C00L C019 -25.3(4) . . . . ?
N001 C005 C00L C0 174.9(5) . . . . ?
N001 C005 C00L C2 -1.5(4) . . . . ?
N001 C00D C00G N003 0.94(17) . . . . ?
N001 C00D C00G C00H 179.20(13) . . . . ?
N001 C00D C00Q C00N -1.0(3) . . . . ?
N001 C00D C00Q C00R 179.17(14) . . . . ?
N002 C006 C00K C008 -0.05(18) . . . . ?
N002 C006 C00K C011 -179.59(15) . . . . ?
N002 C006 C00M C01B 179.37(16) . . . . ?
N002 C007 C008 C00K 1.54(18) . . . . ?
N002 C007 C008 C012 -177.86(14) . . . . ?
N002 C007 C00T C016 177.61(16) . . . . ?
N002 C00C C00U C00J 179.62(14) . . . . ?
N003 C005 C00L C010 -16.6(4) . . . . ?
N003 C005 C00L C019 156.2(4) . . . . ?
N003 C005 C00L C0 -3.6(5) . . . . ?
N003 C005 C00L C2 180.0(4) . . . . ?
N003 C00G C00H C00I 177.11(14) . . . . ?
N003 C00G C00H C00Z -1.6(3) . . . . ?
C004 N001 C005 N003 174.03(14) . . . . ?
C004 N001 C005 C00L -4.6(2) . . . . ?
C004 N001 C00D C00G -174.19(14) . . . . ?
C004 N001 C00D C00Q 7.6(2) . . . . ?
C004 C00E C01A C017 -0.8(3) . . . . ?
C004 C00W C014 C017 -0.2(3) . . . . ?
C005 N001 C004 C00E -82.8(2) . . . . ?
C005 N001 C004 C00W 98.92(19) . . . . ?
C005 N001 C00D C00G -1.41(16) . . . . ?
C005 N001 C00D C00Q -179.62(15) . . . . ?
C005 N003 C00G C00D -0.06(17) . . . . ?
C005 N003 C00G C00H -178.21(15) . . . . ?
C005 C00L C019 C00P -176.7(4) . . . . ?
C005 C00L C0 C1 177.1(7) . . . . ?
C005 C00L C2 N0 -176.9(4) . . . . ?
C006 N002 C007 C008 -1.61(17) . . . . ?
C006 N002 C007 C00T 179.72(16) . . . . ?
C006 N002 C00C C00A -81.4(2) . . . . ?
C006 N002 C00C C00U 99.87(19) . . . . ?
C006 C00K C011 C01C 0.1(3) . . . . ?
C006 C00M C01B C01C 0.4(3) . . . . ?
C007 N002 C006 C00K 1.01(17) . . . . ?
C007 N002 C006 C00M -178.93(16) . . . . ?
C007 N002 C00C C00A 80.4(2) . . . . ?
C007 N002 C00C C00U -98.36(19) . . . . ?
C007 C008 C00K C006 -0.91(18) . . . . ?
C007 C008 C00K C011 178.54(19) . . . . ?
C007 C008 C012 C018 -0.1(3) . . . . ?
C007 C00T C016 C018 0.2(3) . . . . ?
C008 C007 C00T C016 -0.9(3) . . . . ?
C008 C00K C011 C01C -179.33(18) . . . . ?
C008 C012 C018 C016 -0.6(3) . . . . ?
N009 C010 C00L C005 176.9(6) . . . . ?
N009 C010 C00L C019 3.6(8) . . . . ?
N009 C00O C00F C00A -12.9(4) . . . . ?
N009 C00O C00F C00B 165.7(4) . . . . ?
C010 N009 C00O C00P -7.6(7) . . . . ?
C010 N009 C00O C00F 179.7(5) . . . . ?
C010 C00L C019 C00P -4.2(6) . . . . ?
C00L C019 C00P C00O -1.5(7) . . . . ?
C019 C00P C00O N009 7.3(5) . . . . ?
C019 C00P C00O C00F 179.9(4) . . . . ?
C00P C00O C00F C00A 174.7(4) . . . . ?
C00P C00O C00F C00B -6.6(4) . . . . ?
C00O N009 C010 C00L 2.3(10) . . . . ?
C00O N0 C2 C00L -5.1(7) . . . . ?
C00O C1 C0 C00L 4.3(14) . . . . ?
C00A C00C C00U C00J 0.9(2) . . . . ?
C00B C00J C00U C00C 0.0(3) . . . . ?
C00C N002 C006 C00K 165.15(14) . . . . ?
C00C N002 C006 C00M -14.8(3) . . . . ?
C00C N002 C007 C008 -166.01(14) . . . . ?
C00C N002 C007 C00T 15.3(3) . . . . ?
C00C C00A C00F C00O 179.26(14) . . . . ?
C00C C00A C00F C00B 0.6(2) . . . . ?
C00D N001 C004 C00E 88.46(19) . . . . ?
C00D N001 C004 C00W -89.86(19) . . . . ?
C00D N001 C005 N003 1.48(17) . . . . ?
C00D N001 C005 C00L -177.17(14) . . . . ?
C00D C00G C00H C00I -0.9(2) . . . . ?
C00D C00G C00H C00Z -179.53(15) . . . . ?
C00D C00Q C00R C00I 3.1(2) . . . . ?
C00D C00Q C00R C00V -175.92(14) . . . . ?
C00E C004 C00W C014 -1.0(3) . . . . ?
C00F C00O N0 C2 -178.3(4) . . . . ?
C00F C00O C1 C0 179.0(6) . . . . ?
C00F C00A C00C N002 -179.95(13) . . . . ?
C00F C00A C00C C00U -1.2(2) . . . . ?
C00F C00B C00J C00U -0.6(2) . . . . ?
C00G N003 C005 N001 -0.88(17) . . . . ?
C00G N003 C005 C00L 177.84(13) . . . . ?
C00G C00D C00Q C00N -178.88(15) . . . . ?
C00G C00D C00Q C00R 1.2(2) . . . . ?
C00G C00H C00I C00R 5.1(2) . . . . ?
C00G C00H C00I C013 -174.01(14) . . . . ?
C00G C00H C00Z C00X 175.08(16) . . . . ?
C00H C00I C00R C00Q -6.4(2) . . . . ?
C00H C00I C00R C00V 172.59(14) . . . . ?
C00H C00I C013 C015 -2.8(2) . . . . ?
C00I C00H C00Z C00X -3.6(3) . . . . ?
C00I C00R C00V C00Y 178.21(15) . . . . ?
C00I C013 C015 C00X -0.2(3) . . . . ?
C00J C00B C00F C00O -178.34(14) . . . . ?
C00J C00B C00F C00A 0.3(2) . . . . ?
C00K C006 C00M C01B -0.6(2) . . . . ?
C00K C008 C012 C018 -179.33(19) . . . . ?
C00K C011 C01C C01B -0.3(3) . . . . ?
C00M C006 C00K C008 179.90(14) . . . . ?
C00M C006 C00K C011 0.4(2) . . . . ?
C00M C01B C01C C011 0.0(3) . . . . ?
C00N C00Q C00R C00I -176.79(14) . . . . ?
C00N C00Q C00R C00V 4.2(2) . . . . ?
C00N C00S C00Y C00V 1.5(3) . . . . ?
C00Q C00D C00G N003 179.33(13) . . . . ?
C00Q C00D C00G C00H -2.4(2) . . . . ?
C00Q C00N C00S C00Y 0.0(3) . . . . ?
C00Q C00R C00V C00Y -2.8(2) . . . . ?
C00R C00I C013 C015 178.10(16) . . . . ?
C00R C00V C00Y C00S -0.1(3) . . . . ?
C00S C00N C00Q C00D 177.21(15) . . . . ?
C00S C00N C00Q C00R -2.9(2) . . . . ?
C00T C007 C008 C00K -179.70(15) . . . . ?
C00T C007 C008 C012 0.9(2) . . . . ?
C00T C016 C018 C012 0.6(3) . . . . ?
C00W C004 C00E C01A 1.5(3) . . . . ?
C00W C014 C017 C01A 0.8(3) . . . . ?
C00Z C00H C00I C00R -176.23(15) . . . . ?
C00Z C00H C00I C013 4.7(2) . . . . ?
C00Z C00X C015 C013 1.5(3) . . . . ?
C012 C008 C00K C006 178.35(18) . . . . ?
C012 C008 C00K C011 -2.2(3) . . . . ?
C013 C00I C00R C00Q 172.64(14) . . . . ?
C013 C00I C00R C00V -8.4(2) . . . . ?
C014 C017 C01A C00E -0.3(3) . . . . ?
C015 C00X C00Z C00H 0.4(3) . . . . ?
N0 C00O C00F C00A 153.9(3) . . . . ?
N0 C00O C00F C00B -27.4(4) . . . . ?
N0 C00O C1 C0 -2.4(9) . . . . ?
C1 C00O C00F C00A -27.3(6) . . . . ?
C1 C00O C00F C00B 151.3(6) . . . . ?
C1 C00O N0 C2 3.1(6) . . . . ?
C0 C00L C2 N0 6.4(5) . . . . ?
C2 C00L C0 C1 -6.0(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 1.164
_oxdiff_exptl_absorpt_empirical_full_min 0.911
####################################################################### 
# 
# 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_mp9pcz
_database_code_depnum_ccdc_archive 'CCDC 2255990'
loop_
_audit_author_name
_audit_author_address
'Xu Qiu'
;Shandong University of Science and Technology
China
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-12-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H28 N4'
_chemical_formula_sum            'C44 H28 N4'
_chemical_formula_weight         612.70
_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                   18.8335(4)
_cell_length_b                   5.62960(10)
_cell_length_c                   29.0221(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.602(2)
_cell_angle_gamma                90
_cell_volume                     3024.54(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7335
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.2750
_cell_measurement_theta_min      2.5920
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.617
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            17346
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.196
_diffrn_reflns_theta_min         2.595
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     18.00  43.00   0.50    0.72    --    5.00   9.00  85.00   50
  2  ω    -57.00 -32.00   0.50    0.72    --    5.00  -9.00 -85.00   50
  3  ω   -162.00-137.00   0.50    0.72    -- -100.10  -9.00 -85.00   50
  4  ω    -94.00 -62.00   0.50    0.72    -- -100.10   9.00  85.00   64
  5  ω    -36.00 -10.00   0.50    0.50    --    1.00 -57.00 -90.00   52
  6  ω    -13.00  89.00   0.50    0.50    --    1.00  72.00 -60.00  204
  7  ω    -78.00  18.00   0.50    0.72    --    5.00 -57.00   0.00  192
  8  ω   -112.00 -28.00   0.50    0.72    -- -100.10  38.00 120.00  168
  9  ω   -189.00-144.00   0.50    0.72    -- -100.10 -72.00  60.00   90
 10  ω   -114.00 -11.00   0.50    0.72    -- -100.10  19.00-180.00  206
 11  ω   -114.00 -57.00   0.50    0.72    -- -100.10  72.00 -60.00  114
 12  ω    -64.00 -14.00   0.50    0.72    -- -100.10  72.00 -30.00  100
 13  ω   -107.00 -82.00   0.50    0.72    -- -100.10  72.00-150.00   50
 14  ω    -58.00 -33.00   0.50    0.72    -- -100.10  72.00-150.00   50
 15  ω   -128.00 -91.00   0.50    0.72    -- -100.10 -19.00-180.00   74
 16  ω   -106.00 -11.00   0.50    0.72    -- -100.10  38.00  30.00  190
 17  ω   -189.00-161.00   0.50    0.72    -- -100.10 -72.00 -30.00   56
 18  ω   -108.00 -48.00   0.50    0.72    -- -100.10  72.00-120.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0644303000
_diffrn_orient_matrix_UB_12      -0.0301902000
_diffrn_orient_matrix_UB_13      0.0407496000
_diffrn_orient_matrix_UB_21      0.0521050000
_diffrn_orient_matrix_UB_22      -0.0005980000
_diffrn_orient_matrix_UB_23      -0.0351495000
_diffrn_orient_matrix_UB_31      0.0073990000
_diffrn_orient_matrix_UB_32      0.2721007000
_diffrn_orient_matrix_UB_33      0.0044803000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5127
_reflns_number_total             5926
_reflns_odcompleteness_completeness 99.58
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         5926
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+0.9649P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0901
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00M(H00M), C00O(H00O), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012),
 C013(H013), C014(H014), C015(H015), C016(H016), C017(H017), C018(H018),
 C019(H019), C01A(H01A), C01B(H01B), C01C(H01C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N001 N 0.50221(5) -0.02006(18) 0.19830(3) 0.0226(2) Uani 1 1 d . . . . .
N002 N 0.59662(5) 0.45994(18) 0.31534(3) 0.0239(2) Uani 1 1 d . . . . .
N003 N 0.39956(5) 0.01329(18) 0.22667(3) 0.0242(2) Uani 1 1 d . . . . .
N004 N 0.67876(5) 1.25891(19) 0.47321(3) 0.0252(2) Uani 1 1 d . . . . .
C005 C 0.57744(6) -0.0051(2) 0.19527(4) 0.0214(2) Uani 1 1 d . . . . .
C006 C 0.39181(6) -0.1597(2) 0.19247(4) 0.0230(2) Uani 1 1 d . . . . .
C007 C 0.46633(6) 0.0919(2) 0.22973(4) 0.0225(2) Uani 1 1 d . . . . .
C008 C 0.58367(6) 0.7892(2) 0.36574(4) 0.0220(2) Uani 1 1 d . . . . .
C009 C 0.45347(6) -0.1808(2) 0.17383(4) 0.0226(2) Uani 1 1 d . . . . .
C00A C 0.64744(6) 1.1014(2) 0.43680(4) 0.0237(2) Uani 1 1 d . . . . .
C00B C 0.49683(6) 0.2774(2) 0.26319(4) 0.0223(2) Uani 1 1 d . . . . .
C00C C 0.46016(6) -0.3404(2) 0.13626(4) 0.0228(2) Uani 1 1 d . . . . .
C00D C 0.56973(6) 0.2958(2) 0.28375(4) 0.0243(3) Uani 1 1 d . . . . .
H00D H 0.601652 0.186419 0.274817 0.029 Uiso 1 1 calc R . . . .
C00E C 0.65415(6) 0.7539(2) 0.39000(4) 0.0250(3) Uani 1 1 d . . . . .
H00E H 0.680306 0.624065 0.382413 0.030 Uiso 1 1 calc R . . . .
C00F C 0.54604(6) 0.9868(2) 0.37779(4) 0.0252(3) Uani 1 1 d . . . . .
H00F H 0.499156 1.015019 0.362064 0.030 Uiso 1 1 calc R . . . .
C00G C 0.75248(7) 1.5374(2) 0.51432(4) 0.0243(3) Uani 1 1 d . . . . .
C00H C 0.68798(7) 1.5193(2) 0.53433(4) 0.0252(3) Uani 1 1 d . . . . .
C00I C 0.33144(6) -0.3172(2) 0.17884(4) 0.0244(3) Uani 1 1 d . . . . .
C00J C 0.64398(7) 1.3457(2) 0.50852(4) 0.0253(3) Uani 1 1 d . . . . .
C00K C 0.40342(6) -0.5097(2) 0.12451(4) 0.0245(3) Uani 1 1 d . . . . .
C00L C 0.33918(6) -0.5003(2) 0.14656(4) 0.0250(3) Uani 1 1 d . . . . .
C00M C 0.68592(7) 0.9072(2) 0.42501(4) 0.0256(3) Uani 1 1 d . . . . .
H00M H 0.732952 0.880427 0.440622 0.031 Uiso 1 1 calc R . . . .
C00N C 0.55086(6) 0.6170(2) 0.32923(4) 0.0220(2) Uani 1 1 d . . . . .
C00O C 0.51617(7) -0.3318(2) 0.11009(4) 0.0261(3) Uani 1 1 d . . . . .
H00O H 0.551669 -0.215564 0.116755 0.031 Uiso 1 1 calc R . . . .
C00P C 0.74495(6) 1.3753(2) 0.47665(4) 0.0234(2) Uani 1 1 d . . . . .
C00Q C 0.44994(6) 0.4412(2) 0.27782(4) 0.0258(3) Uani 1 1 d . . . . .
H00Q H 0.400799 0.436305 0.265368 0.031 Uiso 1 1 calc R . . . .
C00R C 0.60269(7) 0.1868(2) 0.17341(4) 0.0272(3) Uani 1 1 d . . . . .
H00R H 0.571788 0.310551 0.161819 0.033 Uiso 1 1 calc R . . . .
C00S C 0.47687(6) 0.6105(2) 0.31085(4) 0.0262(3) Uani 1 1 d . . . . .
H00S H 0.445910 0.719851 0.320842 0.031 Uiso 1 1 calc R . . . .
C00T C 0.62282(7) -0.1892(2) 0.21320(4) 0.0281(3) Uani 1 1 d . . . . .
H00T H 0.605355 -0.316358 0.228265 0.034 Uiso 1 1 calc R . . . .
C00U C 0.51907(7) -0.4929(2) 0.07483(4) 0.0298(3) Uani 1 1 d . . . . .
H00U H 0.555958 -0.484188 0.057549 0.036 Uiso 1 1 calc R . . . .
C00V C 0.57745(7) 1.1411(2) 0.41276(4) 0.0266(3) Uani 1 1 d . . . . .
H00V H 0.551652 1.271946 0.420235 0.032 Uiso 1 1 calc R . . . .
C00W C 0.79678(7) 1.3595(2) 0.44816(4) 0.0281(3) Uani 1 1 d . . . . .
H00W H 0.791284 1.254842 0.422955 0.034 Uiso 1 1 calc R . . . .
C00X C 0.81367(7) 1.6811(2) 0.52438(4) 0.0291(3) Uani 1 1 d . . . . .
H00X H 0.819369 1.787214 0.549347 0.035 Uiso 1 1 calc R . . . .
C00Y C 0.46652(7) -0.6691(2) 0.06514(4) 0.0324(3) Uani 1 1 d . . . . .
H00Y H 0.469566 -0.782519 0.042281 0.039 Uiso 1 1 calc R . . . .
C00Z C 0.57875(7) 1.2769(2) 0.52033(5) 0.0312(3) Uani 1 1 d . . . . .
H00Z H 0.550611 1.158017 0.503832 0.037 Uiso 1 1 calc R . . . .
C010 C 0.26876(7) -0.3008(2) 0.19836(4) 0.0288(3) Uani 1 1 d . . . . .
H010 H 0.263987 -0.178080 0.219030 0.035 Uiso 1 1 calc R . . . .
C011 C 0.66495(7) 1.6344(2) 0.57157(4) 0.0306(3) Uani 1 1 d . . . . .
H011 H 0.693132 1.751992 0.588501 0.037 Uiso 1 1 calc R . . . .
C012 C 0.21425(7) -0.4656(3) 0.18708(4) 0.0319(3) Uani 1 1 d . . . . .
H012 H 0.172814 -0.454749 0.200126 0.038 Uiso 1 1 calc R . . . .
C013 C 0.28234(7) -0.6655(2) 0.13604(5) 0.0315(3) Uani 1 1 d . . . . .
H013 H 0.285929 -0.788492 0.115191 0.038 Uiso 1 1 calc R . . . .
C014 C 0.86566(7) 1.6631(2) 0.49664(4) 0.0316(3) Uani 1 1 d . . . . .
H014 H 0.906961 1.756844 0.503208 0.038 Uiso 1 1 calc R . . . .
C015 C 0.41010(7) -0.6760(2) 0.08926(4) 0.0305(3) Uani 1 1 d . . . . .
H015 H 0.375286 -0.794107 0.082064 0.037 Uiso 1 1 calc R . . . .
C016 C 0.72070(7) 0.0084(3) 0.18624(5) 0.0358(3) Uani 1 1 d . . . . .
H016 H 0.768869 0.012316 0.182923 0.043 Uiso 1 1 calc R . . . .
C017 C 0.59953(8) 1.5701(3) 0.58270(5) 0.0346(3) Uani 1 1 d . . . . .
H017 H 0.583287 1.646176 0.607253 0.042 Uiso 1 1 calc R . . . .
C018 C 0.69465(7) -0.1817(3) 0.20846(5) 0.0343(3) Uani 1 1 d . . . . .
H018 H 0.725558 -0.304995 0.220261 0.041 Uiso 1 1 calc R . . . .
C019 C 0.22167(7) -0.6489(3) 0.15592(5) 0.0348(3) Uani 1 1 d . . . . .
H019 H 0.185124 -0.761164 0.148527 0.042 Uiso 1 1 calc R . . . .
C01A C 0.85684(7) 1.5055(2) 0.45876(5) 0.0313(3) Uani 1 1 d . . . . .
H01A H 0.892154 1.498457 0.440229 0.038 Uiso 1 1 calc R . . . .
C01B C 0.55727(7) 1.3923(3) 0.55765(5) 0.0346(3) Uani 1 1 d . . . . .
H01B H 0.513718 1.350477 0.566212 0.041 Uiso 1 1 calc R . . . .
C01C C 0.67469(7) 0.1926(3) 0.16899(5) 0.0340(3) Uani 1 1 d . . . . .
H01C H 0.692228 0.321061 0.154331 0.041 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
N001 C005 1.4379(14) . ?
N001 C007 1.3831(15) . ?
N001 C009 1.3877(14) . ?
N002 C00D 1.3344(15) . ?
N002 C00N 1.3471(15) . ?
N003 C006 1.3790(15) . ?
N003 C007 1.3205(15) . ?
N004 C00A 1.4218(15) . ?
N004 C00J 1.4016(15) . ?
N004 C00P 1.3954(15) . ?
C005 C00R 1.3811(17) . ?
C005 C00T 1.3823(17) . ?
C006 C009 1.3735(16) . ?
C006 C00I 1.4386(16) . ?
C007 C00B 1.4691(16) . ?
C008 C00E 1.3977(16) . ?
C008 C00F 1.3976(16) . ?
C008 C00N 1.4845(16) . ?
C009 C00C 1.4362(16) . ?
C00A C00M 1.3887(17) . ?
C00A C00V 1.3913(17) . ?
C00B C00D 1.3966(16) . ?
C00B C00Q 1.3959(17) . ?
C00C C00K 1.4256(17) . ?
C00C C00O 1.4095(17) . ?
C00E C00M 1.3829(17) . ?
C00F C00V 1.3829(17) . ?
C00G C00H 1.4433(17) . ?
C00G C00P 1.4110(17) . ?
C00G C00X 1.3943(17) . ?
C00H C00J 1.4052(17) . ?
C00H C011 1.3960(17) . ?
C00I C00L 1.4186(17) . ?
C00I C010 1.4034(17) . ?
C00J C00Z 1.3899(18) . ?
C00K C00L 1.4700(17) . ?
C00K C015 1.4095(17) . ?
C00L C013 1.4084(17) . ?
C00N C00S 1.3978(16) . ?
C00O C00U 1.3761(17) . ?
C00P C00W 1.3934(17) . ?
C00Q C00S 1.3807(17) . ?
C00R C01C 1.3858(18) . ?
C00T C018 1.3855(18) . ?
C00U C00Y 1.3930(19) . ?
C00W C01A 1.3863(18) . ?
C00X C014 1.3812(19) . ?
C00Y C015 1.3763(19) . ?
C00Z C01B 1.3857(18) . ?
C010 C012 1.3775(18) . ?
C011 C017 1.3785(19) . ?
C012 C019 1.396(2) . ?
C013 C019 1.3748(19) . ?
C014 C01A 1.3987(19) . ?
C016 C018 1.385(2) . ?
C016 C01C 1.385(2) . ?
C017 C01B 1.397(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
C007 N001 C005 128.33(10) . . ?
C007 N001 C009 106.08(10) . . ?
C009 N001 C005 124.98(10) . . ?
C00D N002 C00N 118.52(10) . . ?
C007 N003 C006 104.97(10) . . ?
C00J N004 C00A 125.09(10) . . ?
C00P N004 C00A 126.08(10) . . ?
C00P N004 C00J 108.40(10) . . ?
C00R C005 N001 120.01(11) . . ?
C00R C005 C00T 121.20(11) . . ?
C00T C005 N001 118.75(11) . . ?
N003 C006 C00I 127.36(11) . . ?
C009 C006 N003 111.06(10) . . ?
C009 C006 C00I 121.41(11) . . ?
N001 C007 C00B 125.51(10) . . ?
N003 C007 N001 112.20(10) . . ?
N003 C007 C00B 122.29(10) . . ?
C00E C008 C00N 119.90(11) . . ?
C00F C008 C00E 117.75(11) . . ?
C00F C008 C00N 122.34(11) . . ?
N001 C009 C00C 130.86(11) . . ?
C006 C009 N001 105.65(10) . . ?
C006 C009 C00C 123.48(11) . . ?
C00M C00A N004 120.66(11) . . ?
C00M C00A C00V 119.47(11) . . ?
C00V C00A N004 119.87(11) . . ?
C00D C00B C007 124.70(11) . . ?
C00Q C00B C007 118.58(10) . . ?
C00Q C00B C00D 116.63(11) . . ?
C00K C00C C009 115.68(11) . . ?
C00O C00C C009 124.50(11) . . ?
C00O C00C C00K 119.77(11) . . ?
N002 C00D C00B 124.33(11) . . ?
C00M C00E C008 121.58(11) . . ?
C00V C00F C008 121.01(11) . . ?
C00P C00G C00H 107.11(10) . . ?
C00X C00G C00H 132.93(12) . . ?
C00X C00G C00P 119.92(11) . . ?
C00J C00H C00G 106.97(10) . . ?
C011 C00H C00G 133.09(12) . . ?
C011 C00H C00J 119.94(12) . . ?
C00L C00I C006 117.22(11) . . ?
C010 C00I C006 121.97(11) . . ?
C010 C00I C00L 120.71(11) . . ?
N004 C00J C00H 108.85(11) . . ?
C00Z C00J N004 129.53(12) . . ?
C00Z C00J C00H 121.56(11) . . ?
C00C C00K C00L 120.84(11) . . ?
C015 C00K C00C 117.05(11) . . ?
C015 C00K C00L 122.02(11) . . ?
C00I C00L C00K 120.42(11) . . ?
C013 C00L C00I 117.18(12) . . ?
C013 C00L C00K 122.38(11) . . ?
C00E C00M C00A 119.84(11) . . ?
N002 C00N C008 115.91(10) . . ?
N002 C00N C00S 121.10(11) . . ?
C00S C00N C008 122.96(11) . . ?
C00U C00O C00C 120.93(12) . . ?
N004 C00P C00G 108.67(10) . . ?
C00W C00P N004 129.92(11) . . ?
C00W C00P C00G 121.30(11) . . ?
C00S C00Q C00B 119.69(11) . . ?
C005 C00R C01C 119.10(12) . . ?
C00Q C00S C00N 119.73(11) . . ?
C005 C00T C018 119.15(12) . . ?
C00O C00U C00Y 119.71(12) . . ?
C00F C00V C00A 120.34(11) . . ?
C01A C00W C00P 117.55(12) . . ?
C014 C00X C00G 118.87(12) . . ?
C015 C00Y C00U 120.25(12) . . ?
C01B C00Z C00J 117.43(13) . . ?
C012 C010 C00I 120.35(12) . . ?
C017 C011 C00H 118.53(12) . . ?
C010 C012 C019 119.52(12) . . ?
C019 C013 C00L 121.42(13) . . ?
C00X C014 C01A 120.67(12) . . ?
C00Y C015 C00K 122.05(12) . . ?
C01C C016 C018 119.69(12) . . ?
C011 C017 C01B 120.98(12) . . ?
C016 C018 C00T 120.39(13) . . ?
C013 C019 C012 120.81(12) . . ?
C00W C01A C014 121.66(12) . . ?
C00Z C01B C017 121.50(13) . . ?
C016 C01C C00R 120.46(13) . . ?

_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 1.162
_oxdiff_exptl_absorpt_empirical_full_min 0.794
