# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_20180523d
_database_code_depnum_ccdc_archive 'CCDC 1975232'
loop_
_audit_author_name
_audit_author_address
'Lipeng Zhang'
;TIPC, CAS
China
;
_audit_update_record             
;
2020-01-03 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2018-05-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C25 H29 N4), C H2 Cl2'
_chemical_formula_sum            'C51 H60 Cl2 N8'
_chemical_formula_weight         855.97
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1N1
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'
Cl Cl 0.3639 0.7018 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   21.9296(6)
_cell_length_b                   9.8470(3)
_cell_length_c                   22.4505(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.159(3)
_cell_angle_gamma                90
_cell_volume                     4579.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10033
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.0730
_cell_measurement_theta_min      4.1580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18686
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.291
_diffrn_reflns_theta_min         4.012
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -111.00 -14.00   1.00    1.10    --  -39.74 -57.00  60.00   97
  2  ω    -67.00  21.00   1.00    1.10    --  -39.74  77.00-150.00   88
  3  ω    -47.00  -4.00   1.00    1.10    --   39.74   0.00 -90.00   43
  4  ω     34.00 117.00   1.00    5.00    --  107.19 -45.00-120.00   83
  5  ω     27.00 109.00   1.00    5.00    --  107.19 -94.00 -90.00   82
  6  ω     76.00 177.00   1.00    5.00    --  107.19  77.00 150.00  101
  7  ω     25.00  54.00   1.00    5.00    --  107.19 -94.00-150.00   29
  8  ω     34.00 130.00   1.00    5.00    --  107.19 -77.00  60.00   96
  9  ω     27.00  52.00   1.00    5.00    --  107.19 -94.00  90.00   25
 10  ω     39.00 106.00   1.00    5.00    --  107.19-125.00 -90.00   67
;
_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      0.0712263000
_diffrn_orient_matrix_UB_12      0.0447128000
_diffrn_orient_matrix_UB_13      0.0203891000
_diffrn_orient_matrix_UB_21      0.0182129000
_diffrn_orient_matrix_UB_22      -0.1374741000
_diffrn_orient_matrix_UB_23      -0.0224562000
_diffrn_orient_matrix_UB_31      -0.0110631000
_diffrn_orient_matrix_UB_32      0.0601992000
_diffrn_orient_matrix_UB_33      -0.0659681000
_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                8128
_reflns_number_total             8976
_reflns_odcompleteness_completeness 99.92
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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    ?
_refine_diff_density_max         0.954
_refine_diff_density_min         -1.381
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     610
_refine_ls_number_reflns         8976
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0894
_refine_ls_restrained_S_all      1.105
_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)+(0.1307P)²+11.6350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2619
_refine_ls_wR_factor_ref         0.2672
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C51) = Uanis(C51A)
3. Others
 Sof(C47A)=Sof(H47C)=Sof(H47D)=Sof(C48A)=Sof(H48D)=Sof(H48E)=Sof(H48F)=
 Sof(C49A)=Sof(H49C)=Sof(H49D)=Sof(C50A)=Sof(H50D)=Sof(H50E)=Sof(H50F)=Sof(N8A)=
 1-FVAR(1)
 Sof(C47)=Sof(H47A)=Sof(H47B)=Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(H48C)=Sof(C49)=
 Sof(H49A)=Sof(H49B)=Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(H50C)=Sof(N8)=FVAR(1)
 Sof(C51A)=Sof(H51C)=Sof(H51D)=1-FVAR(2)
 Sof(C51)=Sof(H51A)=Sof(H51B)=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C22(H22A,H22B), C24(H24A,H24B), C27(H27A,H27B),
 C29(H29A,H29B), C47(H47A,H47B), C49(H49A,H49B), C47A(H47C,H47D), C49A(H49C,
 H49D), C51(H51A,H51B), C51A(H51C,H51D)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C13(H13), C17(H17), C18(H18), C20(H20),
 C21(H21), C31(H31), C32(H32), C34(H34), C35(H35), C38(H38), C42(H42), C43(H43),
  C45(H45), C46(H46)
4.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C),
 C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C48(H48A,H48B,H48C), C50(H50A,H50B,
 H50C), C48A(H48D,H48E,H48F), C50A(H50D,H50E,H50F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C -0.1423(2) 0.0578(4) 0.3083(2) 0.0418(9) Uani 1 1 d . . . . .
H1A H -0.1031 0.0183 0.3059 0.063 Uiso 1 1 calc GR . . . .
H1B H -0.1731 -0.0127 0.3064 0.063 Uiso 1 1 calc GR . . . .
H1C H -0.1333 0.1065 0.3473 0.063 Uiso 1 1 calc GR . . . .
C2 C -0.16968(17) 0.1549(4) 0.25347(16) 0.0266(7) Uani 1 1 d . . . . .
H2A H -0.1819 0.1035 0.2145 0.032 Uiso 1 1 calc R . . . .
H2B H -0.2085 0.1962 0.2570 0.032 Uiso 1 1 calc R . . . .
C3 C -0.1055(2) 0.2715(5) 0.1478(2) 0.0430(10) Uani 1 1 d . . . . .
H3A H -0.1468 0.2302 0.1274 0.064 Uiso 1 1 calc GR . . . .
H3B H -0.0756 0.2431 0.1273 0.064 Uiso 1 1 calc GR . . . .
H3C H -0.1099 0.3685 0.1453 0.064 Uiso 1 1 calc GR . . . .
C4 C -0.08097(17) 0.2288(4) 0.21596(17) 0.0284(7) Uani 1 1 d . . . . .
H4A H -0.0735 0.1316 0.2181 0.034 Uiso 1 1 calc R . . . .
H4B H -0.0399 0.2731 0.2365 0.034 Uiso 1 1 calc R . . . .
C5 C -0.12029(15) 0.3803(3) 0.28325(15) 0.0217(6) Uani 1 1 d . . . . .
C6 C -0.15572(14) 0.4017(3) 0.32475(15) 0.0216(6) Uani 1 1 d . . . . .
H6 H -0.1834 0.3341 0.3294 0.026 Uiso 1 1 calc R . . . .
C7 C -0.15010(15) 0.5207(3) 0.35854(15) 0.0216(6) Uani 1 1 d . . . . .
H7 H -0.1745 0.5319 0.3851 0.026 Uiso 1 1 calc R . . . .
C8 C -0.10861(14) 0.6251(3) 0.35388(15) 0.0204(6) Uani 1 1 d . . . . .
C9 C -0.07383(15) 0.6050(3) 0.31254(15) 0.0235(7) Uani 1 1 d . . . . .
H9 H -0.0460 0.6728 0.3084 0.028 Uiso 1 1 calc R . . . .
C10 C -0.07955(16) 0.4870(4) 0.27747(16) 0.0247(7) Uani 1 1 d . . . . .
H10 H -0.0563 0.4779 0.2498 0.030 Uiso 1 1 calc R . . . .
C11 C -0.09551(14) 0.7475(3) 0.39443(14) 0.0196(6) Uani 1 1 d . . . . .
C12 C -0.01823(14) 0.8973(3) 0.45421(15) 0.0215(6) Uani 1 1 d . . . . .
C13 C 0.04522(15) 0.9442(3) 0.47458(16) 0.0238(7) Uani 1 1 d . . . . .
H13 H 0.0751 0.9074 0.4578 0.029 Uiso 1 1 calc R . . . .
C14 C 0.06389(14) 1.0459(3) 0.51988(15) 0.0212(6) Uani 1 1 d . . . . .
C15 C 0.14409(14) 1.1841(3) 0.58389(15) 0.0201(6) Uani 1 1 d . . . . .
C16 C 0.21410(14) 1.2130(3) 0.60799(15) 0.0205(6) Uani 1 1 d . . . . .
C17 C 0.24860(15) 1.2445(3) 0.67099(15) 0.0217(6) Uani 1 1 d . . . . .
H17 H 0.2262 1.2579 0.6992 0.026 Uiso 1 1 calc R . . . .
C18 C 0.31514(15) 1.2562(3) 0.69222(16) 0.0238(7) Uani 1 1 d . . . . .
H18 H 0.3365 1.2768 0.7344 0.029 Uiso 1 1 calc R . . . .
C19 C 0.35137(15) 1.2375(3) 0.65097(16) 0.0253(7) Uani 1 1 d . . . . .
C20 C 0.31650(15) 1.2033(4) 0.58802(17) 0.0259(7) Uani 1 1 d . . . . .
H20 H 0.3387 1.1874 0.5598 0.031 Uiso 1 1 calc R . . . .
C21 C 0.24990(15) 1.1929(3) 0.56744(15) 0.0231(7) Uani 1 1 d . . . . .
H21 H 0.2283 1.1720 0.5254 0.028 Uiso 1 1 calc R . . . .
C22 C 0.45387(17) 1.3071(4) 0.73195(18) 0.0349(8) Uani 1 1 d . . . . .
H22A H 0.4263 1.3677 0.7457 0.042 Uiso 1 1 calc R . . . .
H22B H 0.4894 1.3606 0.7278 0.042 Uiso 1 1 calc R . . . .
C23 C 0.48082(19) 1.2002(4) 0.78237(19) 0.0383(9) Uani 1 1 d . . . . .
H23A H 0.5082 1.1395 0.7693 0.057 Uiso 1 1 calc GR . . . .
H23B H 0.4459 1.1499 0.7886 0.057 Uiso 1 1 calc GR . . . .
H23C H 0.5054 1.2435 0.8211 0.057 Uiso 1 1 calc GR . . . .
C24 C 0.45377(16) 1.2039(5) 0.63071(19) 0.0398(10) Uani 1 1 d . . . . .
H24A H 0.4976 1.2379 0.6479 0.048 Uiso 1 1 calc R . . . .
H24B H 0.4350 1.2423 0.5889 0.048 Uiso 1 1 calc R . . . .
C25 C 0.4564(2) 1.0513(6) 0.6246(2) 0.0503(12) Uani 1 1 d . . . . .
H25A H 0.4811 1.0288 0.5977 0.075 Uiso 1 1 calc GR . . . .
H25B H 0.4134 1.0163 0.6068 0.075 Uiso 1 1 calc GR . . . .
H25C H 0.4765 1.0120 0.6655 0.075 Uiso 1 1 calc GR . . . .
N1 N -0.12517(14) 0.2616(3) 0.25020(14) 0.0258(6) Uani 1 1 d . . . . .
N2 N -0.03580(12) 0.7914(3) 0.41215(13) 0.0215(6) Uani 1 1 d . . . . .
N3 N 0.12698(12) 1.0872(3) 0.54131(13) 0.0215(6) Uani 1 1 d . . . . .
N4 N 0.41703(14) 1.2527(3) 0.67021(15) 0.0320(7) Uani 1 1 d . . . . .
C26 C 0.7367(3) 0.3636(5) 0.9911(2) 0.0578(14) Uani 1 1 d . . . . .
H26A H 0.6979 0.4129 0.9700 0.087 Uiso 1 1 calc GR . . . .
H26B H 0.7679 0.4238 1.0186 0.087 Uiso 1 1 calc GR . . . .
H26C H 0.7273 0.2913 1.0154 0.087 Uiso 1 1 calc GR . . . .
C27 C 0.76339(19) 0.3059(4) 0.94338(17) 0.0351(8) Uani 1 1 d . . . . .
H27A H 0.7736 0.3800 0.9198 0.042 Uiso 1 1 calc R . . . .
H27B H 0.8034 0.2590 0.9652 0.042 Uiso 1 1 calc R . . . .
C28 C 0.63824(17) 0.0682(4) 0.92534(18) 0.0333(8) Uani 1 1 d . . . . .
H28A H 0.6084 0.0745 0.8832 0.050 Uiso 1 1 calc GR . . . .
H28B H 0.6300 0.1401 0.9505 0.050 Uiso 1 1 calc GR . . . .
H28C H 0.6331 -0.0178 0.9432 0.050 Uiso 1 1 calc GR . . . .
C29 C 0.70692(16) 0.0806(4) 0.92389(15) 0.0266(7) Uani 1 1 d . . . . .
H29A H 0.7368 0.0693 0.9663 0.032 Uiso 1 1 calc R . . . .
H29B H 0.7148 0.0080 0.8982 0.032 Uiso 1 1 calc R . . . .
C30 C 0.68983(15) 0.2410(3) 0.83606(14) 0.0221(6) Uani 1 1 d . . . . .
C31 C 0.66045(15) 0.1379(3) 0.79232(15) 0.0231(6) Uani 1 1 d . . . . .
H31 H 0.6588 0.0498 0.8067 0.028 Uiso 1 1 calc R . . . .
C32 C 0.63428(14) 0.1651(3) 0.72885(15) 0.0222(6) Uani 1 1 d . . . . .
H32 H 0.6161 0.0945 0.7013 0.027 Uiso 1 1 calc R . . . .
C33 C 0.63423(14) 0.2959(3) 0.70465(14) 0.0206(6) Uani 1 1 d . . . . .
C34 C 0.66062(15) 0.4001(3) 0.74821(15) 0.0217(6) Uani 1 1 d . . . . .
H34 H 0.6596 0.4887 0.7337 0.026 Uiso 1 1 calc R . . . .
C35 C 0.68809(15) 0.3749(3) 0.81203(15) 0.0226(6) Uani 1 1 d . . . . .
H35 H 0.7056 0.4463 0.8395 0.027 Uiso 1 1 calc R . . . .
C36 C 0.60356(14) 0.3279(3) 0.63690(14) 0.0211(6) Uani 1 1 d . . . . .
C37 C 0.54041(14) 0.4754(3) 0.56187(14) 0.0207(6) Uani 1 1 d . . . . .
C38 C 0.51245(15) 0.6028(3) 0.54623(14) 0.0224(6) Uani 1 1 d . . . . .
H38 H 0.5210 0.6709 0.5766 0.027 Uiso 1 1 calc R . . . .
C39 C 0.47143(15) 0.6287(3) 0.48492(14) 0.0208(6) Uani 1 1 d . . . . .
C40 C 0.40019(15) 0.7707(3) 0.41343(14) 0.0212(6) Uani 1 1 d . . . . .
C41 C 0.35987(15) 0.8938(3) 0.40247(14) 0.0224(6) Uani 1 1 d . . . . .
C42 C 0.29475(15) 0.8928(4) 0.36440(15) 0.0239(7) Uani 1 1 d . . . . .
H42 H 0.2764 0.8117 0.3458 0.029 Uiso 1 1 calc R . . . .
C43 C 0.25722(17) 1.0078(4) 0.35368(18) 0.0324(8) Uani 1 1 d . . . . .
H43 H 0.2139 1.0028 0.3290 0.039 Uiso 1 1 calc R . . . .
C44 C 0.2836(2) 1.1324(4) 0.3796(3) 0.0567(15) Uani 1 1 d . . . . .
C45 C 0.3483(2) 1.1330(4) 0.4203(2) 0.0488(13) Uani 1 1 d . . . . .
H45 H 0.3664 1.2135 0.4399 0.059 Uiso 1 1 calc R . . . .
C46 C 0.38491(16) 1.0165(4) 0.43136(17) 0.0290(8) Uani 1 1 d . . . . .
H46 H 0.4272 1.0196 0.4587 0.035 Uiso 1 1 calc R . . . .
C47 C 0.1833(5) 1.2480(9) 0.3229(5) 0.0261(18) Uani 0.578(10) 1 d . . P A 1
H47A H 0.1743 1.1854 0.2877 0.031 Uiso 0.578(10) 1 calc R . P A 1
H47B H 0.1692 1.3376 0.3059 0.031 Uiso 0.578(10) 1 calc R . P A 1
C48 C 0.1452(6) 1.2063(13) 0.3641(5) 0.038(3) Uani 0.578(10) 1 d . . P A 1
H48A H 0.1000 1.2072 0.3400 0.058 Uiso 0.578(10) 1 calc GR . P A 1
H48B H 0.1533 1.2685 0.3987 0.058 Uiso 0.578(10) 1 calc GR . P A 1
H48C H 0.1577 1.1164 0.3799 0.058 Uiso 0.578(10) 1 calc GR . P A 1
C49 C 0.2833(3) 1.3829(6) 0.3633(3) 0.0228(15) Uani 0.578(10) 1 d . . P A 1
H49A H 0.2647 1.4351 0.3249 0.027 Uiso 0.578(10) 1 calc R . P A 1
H49B H 0.3288 1.3704 0.3693 0.027 Uiso 0.578(10) 1 calc R . P A 1
C50 C 0.2768(5) 1.4627(10) 0.4178(5) 0.036(2) Uani 0.578(10) 1 d . . P A 1
H50A H 0.2319 1.4776 0.4118 0.053 Uiso 0.578(10) 1 calc GR . P A 1
H50B H 0.2982 1.5485 0.4204 0.053 Uiso 0.578(10) 1 calc GR . P A 1
H50C H 0.2960 1.4129 0.4562 0.053 Uiso 0.578(10) 1 calc GR . P A 1
N8 N 0.2524(3) 1.2512(5) 0.3553(4) 0.0280(16) Uani 0.578(10) 1 d . . P A 1
C47A C 0.1712(6) 1.2464(15) 0.3436(7) 0.028(3) Uani 0.422(10) 1 d . . P A 2
H47C H 0.1687 1.1911 0.3071 0.033 Uiso 0.422(10) 1 calc R . P A 2
H47D H 0.1600 1.3389 0.3293 0.033 Uiso 0.422(10) 1 calc R . P A 2
C48A C 0.1226(8) 1.194(2) 0.3740(10) 0.046(4) Uani 0.422(10) 1 d . . P A 2
H48D H 0.0795 1.2115 0.3465 0.069 Uiso 0.422(10) 1 calc GR . P A 2
H48E H 0.1295 1.2387 0.4136 0.069 Uiso 0.422(10) 1 calc GR . P A 2
H48F H 0.1283 1.0976 0.3809 0.069 Uiso 0.422(10) 1 calc GR . P A 2
C49A C 0.2585(4) 1.3630(8) 0.4269(4) 0.027(2) Uani 0.422(10) 1 d . . P A 2
H49C H 0.2875 1.3353 0.4679 0.032 Uiso 0.422(10) 1 calc R . P A 2
H49D H 0.2215 1.4068 0.4331 0.032 Uiso 0.422(10) 1 calc R . P A 2
C50A C 0.2929(6) 1.4638(15) 0.3979(7) 0.040(3) Uani 0.422(10) 1 d . . P A 2
H50D H 0.2646 1.4908 0.3571 0.060 Uiso 0.422(10) 1 calc GR . P A 2
H50E H 0.3309 1.4222 0.3936 0.060 Uiso 0.422(10) 1 calc GR . P A 2
H50F H 0.3051 1.5422 0.4246 0.060 Uiso 0.422(10) 1 calc GR . P A 2
N8A N 0.2372(4) 1.2435(8) 0.3877(5) 0.031(2) Uani 0.422(10) 1 d . . P A 2
N5 N 0.71967(15) 0.2112(3) 0.89884(13) 0.0285(6) Uani 1 1 d . . . . .
N6 N 0.57644(13) 0.4484(3) 0.62372(12) 0.0223(6) Uani 1 1 d . . . . .
N7 N 0.43909(13) 0.7506(3) 0.47140(12) 0.0220(6) Uani 1 1 d . . . . .
Cl1 Cl 0.12403(7) 0.49661(15) 0.47610(7) 0.0637(4) Uani 1 1 d . . . . .
Cl2 Cl 0.00699(8) 0.33697(19) 0.43462(10) 0.0931(7) Uani 1 1 d . . . . .
C51 C 0.0459(4) 0.4822(9) 0.4235(4) 0.0579(19) Uani 0.609(10) 1 d . . P B 1
H51A H 0.0211 0.5607 0.4281 0.069 Uiso 0.609(10) 1 calc R . P B 1
H51B H 0.0474 0.4825 0.3808 0.069 Uiso 0.609(10) 1 calc R . P B 1
C51A C 0.0402(6) 0.4790(15) 0.4684(6) 0.0579(19) Uani 0.391(10) 1 d . . P B 2
H51C H 0.0360 0.4841 0.5100 0.069 Uiso 0.391(10) 1 calc R . P B 2
H51D H 0.0165 0.5548 0.4439 0.069 Uiso 0.391(10) 1 calc R . P B 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
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.518(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N1 1.453(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C3 C4 1.505(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.457(4) . ?
C5 C6 1.411(5) . ?
C5 C10 1.412(5) . ?
C5 N1 1.370(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.399(4) . ?
C8 C9 1.395(5) . ?
C8 C11 1.480(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(5) . ?
C10 H10 0.9300 . ?
C11 C15 1.472(4) 3_576 ?
C11 N2 1.311(4) . ?
C12 C13 1.393(4) . ?
C12 C14 1.427(4) 3_576 ?
C12 N2 1.374(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.390(5) . ?
C14 C12 1.427(4) 3_576 ?
C14 N3 1.369(4) . ?
C15 C11 1.472(4) 3_576 ?
C15 C16 1.478(4) . ?
C15 N3 1.315(4) . ?
C16 C17 1.403(4) . ?
C16 C21 1.398(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.416(5) . ?
C19 C20 1.409(5) . ?
C19 N4 1.369(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(4) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.517(5) . ?
C22 N4 1.458(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.511(7) . ?
C24 N4 1.461(5) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C26 C27 1.491(7) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 N5 1.470(5) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C28 C29 1.522(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 N5 1.467(5) . ?
C30 C31 1.413(5) . ?
C30 C35 1.421(5) . ?
C30 N5 1.377(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.377(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.397(5) . ?
C33 C34 1.404(4) . ?
C33 C36 1.481(4) . ?
C34 H34 0.9300 . ?
C34 C35 1.382(4) . ?
C35 H35 0.9300 . ?
C36 C40 1.472(5) 3_666 ?
C36 N6 1.317(4) . ?
C37 C38 1.389(5) . ?
C37 C39 1.429(5) 3_666 ?
C37 N6 1.380(4) . ?
C38 H38 0.9300 . ?
C38 C39 1.399(4) . ?
C39 C37 1.429(5) 3_666 ?
C39 N7 1.377(4) . ?
C40 C36 1.472(5) 3_666 ?
C40 C41 1.473(5) . ?
C40 N7 1.316(4) . ?
C41 C42 1.403(4) . ?
C41 C46 1.396(5) . ?
C42 H42 0.9300 . ?
C42 C43 1.374(5) . ?
C43 H43 0.9300 . ?
C43 C44 1.398(5) . ?
C44 C45 1.413(5) . ?
C44 N8 1.375(6) . ?
C44 N8A 1.545(10) . ?
C45 H45 0.9300 . ?
C45 C46 1.375(5) . ?
C46 H46 0.9300 . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C47 C48 1.494(14) . ?
C47 N8 1.450(11) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C49 C50 1.501(10) . ?
C49 N8 1.446(8) . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C47A H47C 0.9700 . ?
C47A H47D 0.9700 . ?
C47A C48A 1.532(18) . ?
C47A N8A 1.461(14) . ?
C48A H48D 0.9600 . ?
C48A H48E 0.9600 . ?
C48A H48F 0.9600 . ?
C49A H49C 0.9700 . ?
C49A H49D 0.9700 . ?
C49A C50A 1.516(15) . ?
C49A N8A 1.452(11) . ?
C50A H50D 0.9600 . ?
C50A H50E 0.9600 . ?
C50A H50F 0.9600 . ?
Cl1 C51 1.739(8) . ?
Cl1 C51A 1.797(15) . ?
Cl2 C51 1.725(10) . ?
Cl2 C51A 1.643(15) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C51A H51C 0.9700 . ?
C51A H51D 0.9700 . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
N1 C2 C1 113.7(3) . . ?
N1 C2 H2A 108.8 . . ?
N1 C2 H2B 108.8 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
N1 C4 C3 113.3(3) . . ?
N1 C4 H4A 108.9 . . ?
N1 C4 H4B 108.9 . . ?
C6 C5 C10 116.9(3) . . ?
N1 C5 C6 121.5(3) . . ?
N1 C5 C10 121.6(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.1 . . ?
C6 C7 C8 121.7(3) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 C11 123.5(3) . . ?
C9 C8 C7 117.2(3) . . ?
C9 C8 C11 119.1(3) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 C8 122.0(3) . . ?
C10 C9 H9 119.0 . . ?
C5 C10 H10 119.5 . . ?
C9 C10 C5 120.9(3) . . ?
C9 C10 H10 119.5 . . ?
C15 C11 C8 124.1(3) 3_576 . ?
N2 C11 C8 115.3(3) . . ?
N2 C11 C15 120.5(3) . 3_576 ?
C13 C12 C14 119.7(3) . 3_576 ?
N2 C12 C13 120.1(3) . . ?
N2 C12 C14 120.1(3) . 3_576 ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C12 120.2(3) . 3_576 ?
N3 C14 C12 120.2(3) . 3_576 ?
N3 C14 C13 119.5(3) . . ?
C11 C15 C16 124.6(3) 3_576 . ?
N3 C15 C11 120.5(3) . 3_576 ?
N3 C15 C16 114.8(3) . . ?
C17 C16 C15 124.3(3) . . ?
C21 C16 C15 118.2(3) . . ?
C21 C16 C17 117.1(3) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.7(3) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.2(3) . . ?
C19 C18 H18 119.4 . . ?
C20 C19 C18 116.8(3) . . ?
N4 C19 C18 122.5(3) . . ?
N4 C19 C20 120.7(3) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.2(3) . . ?
C21 C20 H20 119.4 . . ?
C16 C21 H21 119.0 . . ?
C20 C21 C16 122.0(3) . . ?
C20 C21 H21 119.0 . . ?
H22A C22 H22B 107.6 . . ?
C23 C22 H22A 108.7 . . ?
C23 C22 H22B 108.7 . . ?
N4 C22 H22A 108.7 . . ?
N4 C22 H22B 108.7 . . ?
N4 C22 C23 114.4(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
H24A C24 H24B 107.5 . . ?
C25 C24 H24A 108.4 . . ?
C25 C24 H24B 108.4 . . ?
N4 C24 H24A 108.4 . . ?
N4 C24 H24B 108.4 . . ?
N4 C24 C25 115.3(4) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C2 N1 C4 116.1(3) . . ?
C5 N1 C2 121.6(3) . . ?
C5 N1 C4 121.8(3) . . ?
C11 N2 C12 119.1(3) . . ?
C15 N3 C14 119.1(3) . . ?
C19 N4 C22 122.5(3) . . ?
C19 N4 C24 120.3(3) . . ?
C22 N4 C24 117.0(3) . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C27 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
C27 C26 H26C 109.5 . . ?
C26 C27 H27A 108.7 . . ?
C26 C27 H27B 108.7 . . ?
H27A C27 H27B 107.6 . . ?
N5 C27 C26 114.1(4) . . ?
N5 C27 H27A 108.7 . . ?
N5 C27 H27B 108.7 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C29 C28 H28A 109.5 . . ?
C29 C28 H28B 109.5 . . ?
C29 C28 H28C 109.5 . . ?
C28 C29 H29A 108.9 . . ?
C28 C29 H29B 108.9 . . ?
H29A C29 H29B 107.8 . . ?
N5 C29 C28 113.1(3) . . ?
N5 C29 H29A 108.9 . . ?
N5 C29 H29B 108.9 . . ?
C31 C30 C35 117.0(3) . . ?
N5 C30 C31 120.9(3) . . ?
N5 C30 C35 122.1(3) . . ?
C30 C31 H31 119.4 . . ?
C32 C31 C30 121.3(3) . . ?
C32 C31 H31 119.4 . . ?
C31 C32 H32 119.0 . . ?
C31 C32 C33 121.9(3) . . ?
C33 C32 H32 119.0 . . ?
C32 C33 C34 117.0(3) . . ?
C32 C33 C36 122.5(3) . . ?
C34 C33 C36 120.3(3) . . ?
C33 C34 H34 119.0 . . ?
C35 C34 C33 122.1(3) . . ?
C35 C34 H34 119.0 . . ?
C30 C35 H35 119.7 . . ?
C34 C35 C30 120.5(3) . . ?
C34 C35 H35 119.7 . . ?
C40 C36 C33 122.7(3) 3_666 . ?
N6 C36 C33 116.2(3) . . ?
N6 C36 C40 121.0(3) . 3_666 ?
C38 C37 C39 120.2(3) . 3_666 ?
N6 C37 C38 119.2(3) . . ?
N6 C37 C39 120.5(3) . 3_666 ?
C37 C38 H38 120.0 . . ?
C37 C38 C39 120.1(3) . . ?
C39 C38 H38 120.0 . . ?
C38 C39 C37 119.7(3) . 3_666 ?
N7 C39 C37 120.5(3) . 3_666 ?
N7 C39 C38 119.6(3) . . ?
C36 C40 C41 122.4(3) 3_666 . ?
N7 C40 C36 121.0(3) . 3_666 ?
N7 C40 C41 116.6(3) . . ?
C42 C41 C40 122.1(3) . . ?
C46 C41 C40 120.8(3) . . ?
C46 C41 C42 117.1(3) . . ?
C41 C42 H42 118.9 . . ?
C43 C42 C41 122.2(3) . . ?
C43 C42 H42 118.9 . . ?
C42 C43 H43 119.7 . . ?
C42 C43 C44 120.5(3) . . ?
C44 C43 H43 119.7 . . ?
C43 C44 C45 117.6(4) . . ?
C43 C44 N8A 118.2(5) . . ?
C45 C44 N8A 118.8(5) . . ?
N8 C44 C43 119.9(4) . . ?
N8 C44 C45 121.0(4) . . ?
C44 C45 H45 119.4 . . ?
C46 C45 C44 121.1(4) . . ?
C46 C45 H45 119.4 . . ?
C41 C46 H46 119.3 . . ?
C45 C46 C41 121.3(3) . . ?
C45 C46 H46 119.3 . . ?
H47A C47 H47B 107.7 . . ?
C48 C47 H47A 108.8 . . ?
C48 C47 H47B 108.8 . . ?
N8 C47 H47A 108.8 . . ?
N8 C47 H47B 108.8 . . ?
N8 C47 C48 113.6(8) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
H49A C49 H49B 107.7 . . ?
C50 C49 H49A 108.8 . . ?
C50 C49 H49B 108.8 . . ?
N8 C49 H49A 108.8 . . ?
N8 C49 H49B 108.8 . . ?
N8 C49 C50 113.8(6) . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C44 N8 C47 118.8(6) . . ?
C44 N8 C49 124.2(5) . . ?
C49 N8 C47 116.8(5) . . ?
H47C C47A H47D 107.9 . . ?
C48A C47A H47C 109.3 . . ?
C48A C47A H47D 109.3 . . ?
N8A C47A H47C 109.3 . . ?
N8A C47A H47D 109.3 . . ?
N8A C47A C48A 111.8(11) . . ?
C47A C48A H48D 109.5 . . ?
C47A C48A H48E 109.5 . . ?
C47A C48A H48F 109.5 . . ?
H48D C48A H48E 109.5 . . ?
H48D C48A H48F 109.5 . . ?
H48E C48A H48F 109.5 . . ?
H49C C49A H49D 107.9 . . ?
C50A C49A H49C 109.2 . . ?
C50A C49A H49D 109.2 . . ?
N8A C49A H49C 109.2 . . ?
N8A C49A H49D 109.2 . . ?
N8A C49A C50A 112.2(10) . . ?
C49A C50A H50D 109.5 . . ?
C49A C50A H50E 109.5 . . ?
C49A C50A H50F 109.5 . . ?
H50D C50A H50E 109.5 . . ?
H50D C50A H50F 109.5 . . ?
H50E C50A H50F 109.5 . . ?
C47A N8A C44 118.6(8) . . ?
C49A N8A C44 123.5(6) . . ?
C49A N8A C47A 116.4(8) . . ?
C29 N5 C27 117.4(3) . . ?
C30 N5 C27 123.1(3) . . ?
C30 N5 C29 119.5(3) . . ?
C36 N6 C37 117.9(3) . . ?
C40 N7 C39 118.0(3) . . ?
Cl1 C51 H51A 109.0 . . ?
Cl1 C51 H51B 109.0 . . ?
Cl2 C51 Cl1 113.1(4) . . ?
Cl2 C51 H51A 109.0 . . ?
Cl2 C51 H51B 109.0 . . ?
H51A C51 H51B 107.8 . . ?
Cl1 C51A H51C 108.7 . . ?
Cl1 C51A H51D 108.7 . . ?
Cl2 C51A Cl1 114.3(9) . . ?
Cl2 C51A H51C 108.7 . . ?
Cl2 C51A H51D 108.7 . . ?
H51C C51A H51D 107.6 . . ?

_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 1.428
_oxdiff_exptl_absorpt_empirical_full_min 0.341
