# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_20230318_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2299928'
loop_
_audit_author_name
_audit_author_address
'Xin Zhao'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-10-09 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;
_audit_creation_date             2023-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H20 N2'
_chemical_formula_sum            'C27 H20 N2'
_chemical_formula_weight         372.45
_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 0.0033 0.0016 '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 0.0061 0.0033 '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                   9.9299(15)
_cell_length_b                   10.0145(14)
_cell_length_c                   20.865(3)
_cell_angle_alpha                80.776(2)
_cell_angle_beta                 82.041(2)
_cell_angle_gamma                82.681(2)
_cell_volume                     2016.5(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4373
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.84
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12452
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.433
_diffrn_reflns_theta_min         1.992
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6039
_reflns_number_total             8896
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         8896
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      1.137
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1621
_refine_ls_wR_factor_ref         0.1818
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.082) H10(0.082) H7(0.068) H11(0.069) H12(0.082) H2(0.083)
 H3(0.077) H4(0.076) H20(0.068) H5(0.064) H6(0.077) H8(0.084) H9(0.07)
 H14(0.085) H13(0.074) H19(0.068) H18(0.081) H15(0.078) H16(0.079) H17(0.068)
 H21(0.098) H27(0.1) H30(0.094) H36(0.068) H39(0.075) H22(0.076) H23(0.102)
 H24(0.1) H40(0.077) H25(0.081) H26(0.101) H29(0.115) H28(0.095) H35(0.079)
 H34(0.087) H33(0.077) H32(0.072) H31(0.064) H38(0.08) H37(0.071)
 Fixed X: H1(0.59632) H10(0.825858) H7(0.901555) H11(0.848189) H12(0.966469)
 H2(1.116464) H3(0.903615) H4(1.073116) H20(1.039532) H5(0.662525) H6(0.698356)
 H8(0.441471) H9(0.515447) H14(1.140063) H13(1.0251) H19(0.66662) H18(0.594311)
 H15(0.572779) H16(0.628121) H17(0.705097) H21(-0.068188) H27(0.151789)
 H30(0.330412) H36(0.21516) H39(0.208058) H22(0.405946) H23(1.049286)
 H24(0.933385) H40(0.697265) H25(0.69722) H26(0.932402) H29(-0.108314)
 H28(0.067627) H35(0.563339) H34(0.676117) H33(0.721286) H32(0.659593)
 H31(0.548843) H38(0.611233) H37(0.620009)
 Fixed Y: H1(0.142314) H10(0.161679) H7(0.299665) H11(0.767731) H12(0.818431)
 H2(0.652626) H3(-0.068271) H4(0.022558) H20(0.243295) H5(0.28281) H6(0.059988)
 H8(0.25129) H9(0.389623) H14(0.436507) H13(0.383955) H19(0.855391)
 H18(1.002968) H15(0.922046) H16(0.69489) H17(0.54694) H21(0.151565)
 H27(0.084818) H30(0.113977) H36(0.415682) H39(0.500206) H22(0.502394)
 H23(0.207718) H24(0.405849) H40(0.426028) H25(0.047374) H26(0.030109)
 H29(0.260539) H28(0.29767) H35(-0.048095) H34(-0.149) H33(-0.019585)
 H32(0.210533) H31(0.313935) H38(0.417902) H37(0.328624)
 Fixed Z: H1(0.706354) H10(0.678662) H7(0.584007) H11(0.31726) H12(0.215403)
 H2(0.169588) H3(0.390517) H4(0.428742) H20(0.450557) H5(0.396949) H6(0.376634)
 H8(0.637261) H9(0.542879) H14(0.224893) H13(0.327748) H19(0.480078)
 H18(0.555429) H15(0.665574) H16(0.700643) H17(0.626487) H21(1.251754)
 H27(1.27265) H30(1.191032) H36(0.900047) H39(0.791396) H22(0.71955)
 H23(0.944779) H24(0.973085) H40(0.998014) H25(0.96101) H26(0.936956)
 H29(1.14933) H28(1.068807) H35(1.094501) H34(1.182741) H33(1.256816)
 H32(1.242521) H31(1.153437) H38(0.757075) H37(0.865329)
;
_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
N1 N 0.76122(15) 0.45984(14) 0.49925(7) 0.0486(3) Uani 1 1 d . U . . .
N4 N 0.29604(15) 0.29200(15) 1.00429(7) 0.0495(4) Uani 1 1 d . . . . .
N5 N 0.46578(15) 0.20486(14) 1.06272(7) 0.0508(4) Uani 1 1 d . U . . .
C5 C 0.82618(16) 0.42604(15) 0.44030(7) 0.0378(3) Uani 1 1 d . U . . .
C1 C 0.6266(3) 0.1959(2) 0.66768(10) 0.0687(6) Uani 1 1 d . . . . .
H1 H 0.596320 0.142314 0.706354 0.082 Uiso 1 1 calc R U . . .
C2 C 0.7633(2) 0.2087(2) 0.65154(10) 0.0687(6) Uani 1 1 d . . . . .
H10 H 0.825858 0.161679 0.678662 0.082 Uiso 1 1 calc R U . . .
N2 N 0.80851(15) 0.65194(14) 0.43461(7) 0.0458(3) Uani 1 1 d . . . . .
C3 C 0.8087(2) 0.29141(18) 0.59497(9) 0.0563(5) Uani 1 1 d . . . . .
H7 H 0.901555 0.299665 0.584007 0.068 Uiso 1 1 calc R U . . .
C4 C 0.71562(17) 0.36169(16) 0.55482(8) 0.0429(4) Uani 1 1 d . . . . .
C6 C 0.85383(17) 0.54668(16) 0.40142(8) 0.0430(4) Uani 1 1 d . . . . .
C7 C 0.92407(17) 0.57033(17) 0.33454(8) 0.0459(4) Uani 1 1 d . . . . .
C8 C 0.9078(2) 0.7004(2) 0.29926(9) 0.0579(5) Uani 1 1 d . . . . .
H11 H 0.848189 0.767731 0.317260 0.069 Uiso 1 1 calc R U . . .
C9 C 0.9785(2) 0.7309(2) 0.23821(10) 0.0681(6) Uani 1 1 d . . . . .
H12 H 0.966469 0.818431 0.215403 0.082 Uiso 1 1 calc R U . . .
C10 C 1.0674(2) 0.6317(2) 0.21055(10) 0.0689(6) Uani 1 1 d . . . . .
H2 H 1.116464 0.652626 0.169588 0.083 Uiso 1 1 calc R U . . .
C11 C 0.8895(2) 0.0206(2) 0.39981(10) 0.0640(5) Uani 1 1 d . . . . .
H3 H 0.903615 -0.068271 0.390517 0.077 Uiso 1 1 calc R U . . .
C12 C 0.9905(2) 0.0750(2) 0.42228(10) 0.0636(5) Uani 1 1 d . . . . .
H4 H 1.073116 0.022558 0.428742 0.076 Uiso 1 1 calc R U . . .
C13 C 0.97047(19) 0.20694(19) 0.43533(10) 0.0569(5) Uani 1 1 d . . . . .
H20 H 1.039532 0.243295 0.450557 0.068 Uiso 1 1 calc R U . . .
C14 C 0.74533(19) 0.23087(19) 0.40354(9) 0.0534(4) Uani 1 1 d . . . . .
H5 H 0.662525 0.282810 0.396949 0.064 Uiso 1 1 calc R U . . .
C15 C 0.7675(2) 0.0977(2) 0.39112(10) 0.0644(5) Uani 1 1 d . . . . .
H6 H 0.698356 0.059988 0.376634 0.077 Uiso 1 1 calc R U . . .
C16 C 0.5339(2) 0.2623(2) 0.62683(11) 0.0701(6) Uani 1 1 d . . . . .
H8 H 0.441471 0.251290 0.637261 0.084 Uiso 1 1 calc R U . . .
C17 C 0.5781(2) 0.3450(2) 0.57047(10) 0.0586(5) Uani 1 1 d . . . . .
H9 H 0.515447 0.389623 0.542879 0.070 Uiso 1 1 calc R U . . .
C18 C 0.75236(16) 0.59853(16) 0.49468(8) 0.0422(4) Uani 1 1 d . U . . .
C19 C 1.0822(2) 0.5038(2) 0.24383(10) 0.0706(6) Uani 1 1 d . . . . .
H14 H 1.140063 0.436507 0.224893 0.085 Uiso 1 1 calc R U . . .
C20 C 1.0126(2) 0.4720(2) 0.30551(9) 0.0617(5) Uani 1 1 d . . . . .
H13 H 1.025100 0.383955 0.327748 0.074 Uiso 1 1 calc R U . . .
C21 C 0.69654(17) 0.68492(16) 0.54472(8) 0.0434(4) Uani 1 1 d . . . . .
C22 C 0.6606(2) 0.82229(19) 0.52453(9) 0.0571(5) Uani 1 1 d . . . . .
H19 H 0.666620 0.855391 0.480078 0.068 Uiso 1 1 calc R U . . .
C23 C 0.6159(2) 0.9109(2) 0.56969(11) 0.0678(6) Uani 1 1 d . . . . .
H18 H 0.594311 1.002968 0.555429 0.081 Uiso 1 1 calc R U . . .
C24 C 0.6036(2) 0.8628(2) 0.63529(10) 0.0648(5) Uani 1 1 d . . . . .
H15 H 0.572779 0.922046 0.665574 0.078 Uiso 1 1 calc R U . . .
C25 C 0.6368(2) 0.7274(2) 0.65611(10) 0.0658(5) Uani 1 1 d . . . . .
H16 H 0.628121 0.694890 0.700643 0.079 Uiso 1 1 calc R U . . .
C26 C 0.6829(2) 0.63868(19) 0.61161(9) 0.0567(5) Uani 1 1 d . . . . .
H17 H 0.705097 0.546940 0.626487 0.068 Uiso 1 1 calc R U . . .
C27 C 0.0043(2) 0.1667(3) 1.21905(11) 0.0816(7) Uani 1 1 d . . . . .
H21 H -0.068188 0.151565 1.251754 0.098 Uiso 1 1 calc R U . . .
C28 C 0.1343(2) 0.1259(3) 1.23096(12) 0.0836(7) Uani 1 1 d . . . . .
H27 H 0.151789 0.084818 1.272650 0.100 Uiso 1 1 calc R U . . .
C29 C 0.2417(2) 0.1443(2) 1.18193(11) 0.0780(7) Uani 1 1 d . . . . .
H30 H 0.330412 0.113977 1.191032 0.094 Uiso 1 1 calc R U . . .
C30 C 0.22010(19) 0.20725(18) 1.11924(9) 0.0516(4) Uani 1 1 d . . . . .
C31 C 0.32689(18) 0.23377(17) 1.06370(8) 0.0472(4) Uani 1 1 d . . . . .
C32 C 0.41674(18) 0.30152(17) 0.96470(8) 0.0466(4) Uani 1 1 d . . . . .
C33 C 0.41824(18) 0.36112(16) 0.89535(8) 0.0458(4) Uani 1 1 d . . . . .
C34 C 0.2959(2) 0.41458(19) 0.87149(9) 0.0566(5) Uani 1 1 d . . . . .
H36 H 0.215160 0.415682 0.900047 0.068 Uiso 1 1 calc R U . . .
C35 C 0.2915(2) 0.4661(2) 0.80631(10) 0.0628(5) Uani 1 1 d . . . . .
H39 H 0.208058 0.500206 0.791396 0.075 Uiso 1 1 calc R U . . .
C36 C 0.4090(2) 0.4674(2) 0.76345(9) 0.0630(5) Uani 1 1 d . . . . .
H22 H 0.405946 0.502394 0.719550 0.076 Uiso 1 1 calc R U . . .
C37 C 0.9545(3) 0.2155(3) 0.95375(12) 0.0850(8) Uani 1 1 d . . . . .
H23 H 1.049286 0.207718 0.944779 0.102 Uiso 1 1 calc R U . . .
C38 C 0.8854(3) 0.3330(3) 0.97109(11) 0.0832(7) Uani 1 1 d . . . . .
H24 H 0.933385 0.405849 0.973085 0.100 Uiso 1 1 calc R U . . .
C39 C 0.7437(2) 0.3455(2) 0.98589(10) 0.0642(5) Uani 1 1 d . . . . .
H40 H 0.697265 0.426028 0.998014 0.077 Uiso 1 1 calc R U . . .
C40 C 0.67325(18) 0.23823(18) 0.98246(8) 0.0479(4) Uani 1 1 d . . . . .
C41 C 0.7443(2) 0.1203(2) 0.96390(11) 0.0672(5) Uani 1 1 d . . . . .
H25 H 0.697220 0.047374 0.961010 0.081 Uiso 1 1 calc R U . . .
C42 C 0.8852(3) 0.1099(3) 0.94953(12) 0.0841(7) Uani 1 1 d . . . . .
H26 H 0.932402 0.030109 0.936956 0.101 Uiso 1 1 calc R U . . .
C43 C 0.52368(17) 0.24817(15) 0.99972(8) 0.0415(4) Uani 1 1 d . U . . .
C44 C -0.0191(3) 0.2309(3) 1.15794(12) 0.0960(9) Uani 1 1 d . . . . .
H29 H -0.108314 0.260539 1.149330 0.115 Uiso 1 1 calc R U . . .
C45 C 0.0864(2) 0.2519(3) 1.10955(10) 0.0793(7) Uani 1 1 d . . . . .
H28 H 0.067627 0.297670 1.068807 0.095 Uiso 1 1 calc R U . . .
C46 C 0.54438(17) 0.14208(17) 1.11591(8) 0.0460(4) Uani 1 1 d . . . . .
C47 C 0.5826(2) 0.00456(19) 1.12431(10) 0.0654(6) Uani 1 1 d . . . . .
H35 H 0.563339 -0.048095 1.094501 0.079 Uiso 1 1 calc R U . . .
C48 C 0.6497(2) -0.0558(2) 1.17714(11) 0.0729(6) Uani 1 1 d . . . . .
H34 H 0.676117 -0.149000 1.182741 0.087 Uiso 1 1 calc R U . . .
C49 C 0.6772(2) 0.0213(2) 1.22101(10) 0.0638(5) Uani 1 1 d . . . . .
H33 H 0.721286 -0.019585 1.256816 0.077 Uiso 1 1 calc R U . . .
C50 C 0.6401(2) 0.1584(2) 1.21256(9) 0.0602(5) Uani 1 1 d . . . . .
H32 H 0.659593 0.210533 1.242521 0.072 Uiso 1 1 calc R U . . .
C51 C 0.5735(2) 0.22043(19) 1.15943(9) 0.0535(4) Uani 1 1 d . . . . .
H31 H 0.548843 0.313935 1.153437 0.064 Uiso 1 1 calc R U . . .
C52 C 0.5309(2) 0.4166(2) 0.78589(10) 0.0666(5) Uani 1 1 d . . . . .
H38 H 0.611233 0.417902 0.757075 0.080 Uiso 1 1 calc R U . . .
C53 C 0.5362(2) 0.3634(2) 0.85102(9) 0.0593(5) Uani 1 1 d . . . . .
H37 H 0.620009 0.328624 0.865329 0.071 Uiso 1 1 calc R U . . .
C54 C 0.84784(17) 0.28579(16) 0.42587(8) 0.0431(4) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.379(2) . ?
N1 C4 1.455(2) . ?
N1 C18 1.369(2) . ?
N4 C31 1.341(2) . ?
N4 C32 1.363(2) . ?
N5 C31 1.371(2) . ?
N5 C43 1.385(2) . ?
N5 C46 1.459(2) . ?
C5 C6 1.379(2) . ?
C5 C54 1.466(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.370(3) . ?
C1 C16 1.377(3) . ?
C2 H10 0.9300 . ?
C2 C3 1.384(3) . ?
N2 C6 1.349(2) . ?
N2 C18 1.355(2) . ?
C3 H7 0.9300 . ?
C3 C4 1.382(2) . ?
C4 C17 1.384(2) . ?
C6 C7 1.469(2) . ?
C7 C8 1.391(2) . ?
C7 C20 1.390(2) . ?
C8 H11 0.9300 . ?
C8 C9 1.375(3) . ?
C9 H12 0.9300 . ?
C9 C10 1.385(3) . ?
C10 H2 0.9300 . ?
C10 C19 1.356(3) . ?
C11 H3 0.9300 . ?
C11 C12 1.370(3) . ?
C11 C15 1.369(3) . ?
C12 H4 0.9300 . ?
C12 C13 1.376(3) . ?
C13 H20 0.9300 . ?
C13 C54 1.384(2) . ?
C14 H5 0.9300 . ?
C14 C15 1.384(3) . ?
C14 C54 1.383(2) . ?
C15 H6 0.9300 . ?
C16 H8 0.9300 . ?
C16 C17 1.378(3) . ?
C17 H9 0.9300 . ?
C18 C21 1.467(2) . ?
C19 H14 0.9300 . ?
C19 C20 1.383(3) . ?
C20 H13 0.9300 . ?
C21 C22 1.389(2) . ?
C21 C26 1.392(2) . ?
C22 H19 0.9300 . ?
C22 C23 1.387(3) . ?
C23 H18 0.9300 . ?
C23 C24 1.370(3) . ?
C24 H15 0.9300 . ?
C24 C25 1.369(3) . ?
C25 H16 0.9300 . ?
C25 C26 1.380(3) . ?
C26 H17 0.9300 . ?
C27 H21 0.9300 . ?
C27 C28 1.348(3) . ?
C27 C44 1.369(3) . ?
C28 H27 0.9300 . ?
C28 C29 1.380(3) . ?
C29 H30 0.9300 . ?
C29 C30 1.390(3) . ?
C30 C31 1.473(2) . ?
C30 C45 1.377(3) . ?
C32 C33 1.473(2) . ?
C32 C43 1.376(2) . ?
C33 C34 1.388(2) . ?
C33 C53 1.388(3) . ?
C34 H36 0.9300 . ?
C34 C35 1.380(3) . ?
C35 H39 0.9300 . ?
C35 C36 1.369(3) . ?
C36 H22 0.9300 . ?
C36 C52 1.366(3) . ?
C37 H23 0.9300 . ?
C37 C38 1.359(3) . ?
C37 C42 1.353(4) . ?
C38 H24 0.9300 . ?
C38 C39 1.392(3) . ?
C39 H40 0.9300 . ?
C39 C40 1.371(3) . ?
C40 C41 1.378(3) . ?
C40 C43 1.473(2) . ?
C41 H25 0.9300 . ?
C41 C42 1.384(3) . ?
C42 H26 0.9300 . ?
C44 H29 0.9300 . ?
C44 C45 1.363(3) . ?
C45 H28 0.9300 . ?
C46 C47 1.371(2) . ?
C46 C51 1.372(2) . ?
C47 H35 0.9300 . ?
C47 C48 1.383(3) . ?
C48 H34 0.9300 . ?
C48 C49 1.363(3) . ?
C49 H33 0.9300 . ?
C49 C50 1.364(3) . ?
C50 H32 0.9300 . ?
C50 C51 1.390(3) . ?
C51 H31 0.9300 . ?
C52 H38 0.9300 . ?
C52 C53 1.383(3) . ?
C53 H37 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
C5 N1 C4 124.44(13) . . ?
C18 N1 C5 107.06(13) . . ?
C18 N1 C4 128.48(14) . . ?
C31 N4 C32 106.89(15) . . ?
C31 N5 C43 107.04(14) . . ?
C31 N5 C46 128.95(14) . . ?
C43 N5 C46 124.01(14) . . ?
N1 C5 C54 122.60(13) . . ?
C6 C5 N1 106.49(14) . . ?
C6 C5 C54 130.79(14) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C16 120.19(19) . . ?
C16 C1 H1 119.9 . . ?
C1 C2 H10 119.9 . . ?
C1 C2 C3 120.2(2) . . ?
C3 C2 H10 119.9 . . ?
C6 N2 C18 106.91(13) . . ?
C2 C3 H7 120.1 . . ?
C4 C3 C2 119.87(19) . . ?
C4 C3 H7 120.1 . . ?
C3 C4 N1 119.90(15) . . ?
C3 C4 C17 119.53(17) . . ?
C17 C4 N1 120.42(15) . . ?
C5 C6 C7 129.67(15) . . ?
N2 C6 C5 109.79(14) . . ?
N2 C6 C7 120.52(14) . . ?
C8 C7 C6 118.50(16) . . ?
C20 C7 C6 123.71(16) . . ?
C20 C7 C8 117.68(16) . . ?
C7 C8 H11 119.5 . . ?
C9 C8 C7 121.09(18) . . ?
C9 C8 H11 119.5 . . ?
C8 C9 H12 119.9 . . ?
C8 C9 C10 120.26(19) . . ?
C10 C9 H12 119.9 . . ?
C9 C10 H2 120.4 . . ?
C19 C10 C9 119.29(19) . . ?
C19 C10 H2 120.4 . . ?
C12 C11 H3 120.2 . . ?
C15 C11 H3 120.2 . . ?
C15 C11 C12 119.61(19) . . ?
C11 C12 H4 119.8 . . ?
C11 C12 C13 120.32(19) . . ?
C13 C12 H4 119.8 . . ?
C12 C13 H20 119.9 . . ?
C12 C13 C54 120.24(18) . . ?
C54 C13 H20 119.9 . . ?
C15 C14 H5 120.4 . . ?
C54 C14 H5 120.4 . . ?
C54 C14 C15 119.19(17) . . ?
C11 C15 C14 121.05(19) . . ?
C11 C15 H6 119.5 . . ?
C14 C15 H6 119.5 . . ?
C1 C16 H8 120.0 . . ?
C1 C16 C17 120.0(2) . . ?
C17 C16 H8 120.0 . . ?
C4 C17 H9 119.9 . . ?
C16 C17 C4 120.17(19) . . ?
C16 C17 H9 119.9 . . ?
N1 C18 C21 128.72(15) . . ?
N2 C18 N1 109.75(14) . . ?
N2 C18 C21 121.50(14) . . ?
C10 C19 H14 119.5 . . ?
C10 C19 C20 121.0(2) . . ?
C20 C19 H14 119.5 . . ?
C7 C20 H13 119.7 . . ?
C19 C20 C7 120.61(19) . . ?
C19 C20 H13 119.7 . . ?
C22 C21 C18 118.24(16) . . ?
C22 C21 C26 117.80(16) . . ?
C26 C21 C18 123.89(15) . . ?
C21 C22 H19 119.5 . . ?
C23 C22 C21 120.96(19) . . ?
C23 C22 H19 119.5 . . ?
C22 C23 H18 120.0 . . ?
C24 C23 C22 120.09(19) . . ?
C24 C23 H18 120.0 . . ?
C23 C24 H15 120.1 . . ?
C25 C24 C23 119.78(18) . . ?
C25 C24 H15 120.1 . . ?
C24 C25 H16 119.7 . . ?
C24 C25 C26 120.60(19) . . ?
C26 C25 H16 119.7 . . ?
C21 C26 H17 119.6 . . ?
C25 C26 C21 120.75(18) . . ?
C25 C26 H17 119.6 . . ?
C28 C27 H21 120.6 . . ?
C28 C27 C44 118.8(2) . . ?
C44 C27 H21 120.6 . . ?
C27 C28 H27 119.7 . . ?
C27 C28 C29 120.7(2) . . ?
C29 C28 H27 119.7 . . ?
C28 C29 H30 119.3 . . ?
C28 C29 C30 121.5(2) . . ?
C30 C29 H30 119.3 . . ?
C29 C30 C31 125.99(18) . . ?
C45 C30 C29 116.14(18) . . ?
C45 C30 C31 117.84(17) . . ?
N4 C31 N5 110.13(15) . . ?
N4 C31 C30 121.79(16) . . ?
N5 C31 C30 128.08(16) . . ?
N4 C32 C33 120.48(15) . . ?
N4 C32 C43 109.67(15) . . ?
C43 C32 C33 129.84(16) . . ?
C34 C33 C32 119.30(16) . . ?
C34 C33 C53 117.19(16) . . ?
C53 C33 C32 123.48(17) . . ?
C33 C34 H36 119.3 . . ?
C35 C34 C33 121.37(18) . . ?
C35 C34 H36 119.3 . . ?
C34 C35 H39 119.8 . . ?
C36 C35 C34 120.5(2) . . ?
C36 C35 H39 119.8 . . ?
C35 C36 H22 120.4 . . ?
C52 C36 C35 119.24(18) . . ?
C52 C36 H22 120.4 . . ?
C38 C37 H23 120.0 . . ?
C42 C37 H23 120.0 . . ?
C42 C37 C38 120.0(2) . . ?
C37 C38 H24 119.6 . . ?
C37 C38 C39 120.8(2) . . ?
C39 C38 H24 119.6 . . ?
C38 C39 H40 120.3 . . ?
C40 C39 C38 119.4(2) . . ?
C40 C39 H40 120.3 . . ?
C39 C40 C41 119.21(19) . . ?
C39 C40 C43 120.25(17) . . ?
C41 C40 C43 120.53(16) . . ?
C40 C41 H25 119.8 . . ?
C40 C41 C42 120.4(2) . . ?
C42 C41 H25 119.8 . . ?
C37 C42 C41 120.2(2) . . ?
C37 C42 H26 119.9 . . ?
C41 C42 H26 119.9 . . ?
N5 C43 C40 121.16(14) . . ?
C32 C43 N5 106.28(14) . . ?
C32 C43 C40 132.49(15) . . ?
C27 C44 H29 119.5 . . ?
C45 C44 C27 120.9(2) . . ?
C45 C44 H29 119.5 . . ?
C30 C45 H28 119.1 . . ?
C44 C45 C30 121.9(2) . . ?
C44 C45 H28 119.1 . . ?
C47 C46 N5 120.12(15) . . ?
C47 C46 C51 120.29(17) . . ?
C51 C46 N5 119.50(15) . . ?
C46 C47 H35 120.0 . . ?
C46 C47 C48 119.93(18) . . ?
C48 C47 H35 120.0 . . ?
C47 C48 H34 120.0 . . ?
C49 C48 C47 120.00(19) . . ?
C49 C48 H34 120.0 . . ?
C48 C49 H33 119.9 . . ?
C48 C49 C50 120.22(19) . . ?
C50 C49 H33 119.9 . . ?
C49 C50 H32 119.8 . . ?
C49 C50 C51 120.35(18) . . ?
C51 C50 H32 119.8 . . ?
C46 C51 C50 119.20(17) . . ?
C46 C51 H31 120.4 . . ?
C50 C51 H31 120.4 . . ?
C36 C52 H38 119.6 . . ?
C36 C52 C53 120.7(2) . . ?
C53 C52 H38 119.6 . . ?
C33 C53 H37 119.5 . . ?
C52 C53 C33 121.01(19) . . ?
C52 C53 H37 119.5 . . ?
C13 C54 C5 120.19(15) . . ?
C14 C54 C5 120.23(15) . . ?
C14 C54 C13 119.58(16) . . ?

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
N1 C5 C6 N2 0.17(18) . . . . ?
N1 C5 C6 C7 178.51(16) . . . . ?
N1 C5 C54 C13 -95.4(2) . . . . ?
N1 C5 C54 C14 83.8(2) . . . . ?
N1 C4 C17 C16 -173.40(17) . . . . ?
N1 C18 C21 C22 -161.08(17) . . . . ?
N1 C18 C21 C26 21.8(3) . . . . ?
N4 C32 C33 C34 3.6(2) . . . . ?
N4 C32 C33 C53 -174.29(16) . . . . ?
N4 C32 C43 N5 -0.01(18) . . . . ?
N4 C32 C43 C40 -176.80(16) . . . . ?
N5 C46 C47 C48 -176.01(19) . . . . ?
N5 C46 C51 C50 175.59(16) . . . . ?
C5 N1 C4 C3 79.3(2) . . . . ?
C5 N1 C4 C17 -105.23(19) . . . . ?
C5 N1 C18 N2 0.57(18) . . . . ?
C5 N1 C18 C21 -177.67(16) . . . . ?
C5 C6 C7 C8 162.92(18) . . . . ?
C5 C6 C7 C20 -20.9(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C1 C16 C17 C4 -0.1(3) . . . . ?
C2 C1 C16 C17 -1.9(3) . . . . ?
C2 C3 C4 N1 173.34(16) . . . . ?
C2 C3 C4 C17 -2.2(3) . . . . ?
N2 C6 C7 C8 -18.9(2) . . . . ?
N2 C6 C7 C20 157.28(17) . . . . ?
N2 C18 C21 C22 20.9(2) . . . . ?
N2 C18 C21 C26 -156.23(17) . . . . ?
C3 C4 C17 C16 2.1(3) . . . . ?
C4 N1 C5 C6 -179.19(15) . . . . ?
C4 N1 C5 C54 4.4(2) . . . . ?
C4 N1 C18 N2 179.25(15) . . . . ?
C4 N1 C18 C21 1.0(3) . . . . ?
C6 C5 C54 C13 89.1(2) . . . . ?
C6 C5 C54 C14 -91.7(2) . . . . ?
C6 N2 C18 N1 -0.47(18) . . . . ?
C6 N2 C18 C21 177.93(15) . . . . ?
C6 C7 C8 C9 175.45(18) . . . . ?
C6 C7 C20 C19 -175.76(18) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C7 C20 C19 0.4(3) . . . . ?
C8 C9 C10 C19 1.1(3) . . . . ?
C9 C10 C19 C20 -1.6(4) . . . . ?
C10 C19 C20 C7 0.9(3) . . . . ?
C11 C12 C13 C54 0.0(3) . . . . ?
C12 C11 C15 C14 1.2(3) . . . . ?
C12 C13 C54 C5 179.51(16) . . . . ?
C12 C13 C54 C14 0.3(3) . . . . ?
C15 C11 C12 C13 -0.8(3) . . . . ?
C15 C14 C54 C5 -179.12(15) . . . . ?
C15 C14 C54 C13 0.1(3) . . . . ?
C16 C1 C2 C3 1.8(3) . . . . ?
C18 N1 C5 C6 -0.45(17) . . . . ?
C18 N1 C5 C54 -176.88(15) . . . . ?
C18 N1 C4 C3 -99.2(2) . . . . ?
C18 N1 C4 C17 76.3(2) . . . . ?
C18 N2 C6 C5 0.18(18) . . . . ?
C18 N2 C6 C7 -178.34(14) . . . . ?
C18 C21 C22 C23 -175.67(18) . . . . ?
C18 C21 C26 C25 176.28(18) . . . . ?
C20 C7 C8 C9 -1.0(3) . . . . ?
C21 C22 C23 C24 -1.5(3) . . . . ?
C22 C21 C26 C25 -0.8(3) . . . . ?
C22 C23 C24 C25 0.6(3) . . . . ?
C23 C24 C25 C26 0.2(3) . . . . ?
C24 C25 C26 C21 -0.1(3) . . . . ?
C26 C21 C22 C23 1.6(3) . . . . ?
C27 C28 C29 C30 1.1(4) . . . . ?
C27 C44 C45 C30 1.5(4) . . . . ?
C28 C27 C44 C45 0.8(4) . . . . ?
C28 C29 C30 C31 179.1(2) . . . . ?
C28 C29 C30 C45 1.2(4) . . . . ?
C29 C30 C31 N4 178.15(19) . . . . ?
C29 C30 C31 N5 -1.2(3) . . . . ?
C29 C30 C45 C44 -2.4(4) . . . . ?
C31 N4 C32 C33 179.75(14) . . . . ?
C31 N4 C32 C43 0.27(19) . . . . ?
C31 N5 C43 C32 -0.24(17) . . . . ?
C31 N5 C43 C40 176.99(15) . . . . ?
C31 N5 C46 C47 94.5(2) . . . . ?
C31 N5 C46 C51 -82.1(2) . . . . ?
C31 C30 C45 C44 179.4(2) . . . . ?
C32 N4 C31 N5 -0.42(19) . . . . ?
C32 N4 C31 C30 -179.91(15) . . . . ?
C32 C33 C34 C35 -177.16(17) . . . . ?
C32 C33 C53 C52 177.78(17) . . . . ?
C33 C32 C43 N5 -179.43(16) . . . . ?
C33 C32 C43 C40 3.8(3) . . . . ?
C33 C34 C35 C36 -0.9(3) . . . . ?
C34 C33 C53 C52 -0.1(3) . . . . ?
C34 C35 C36 C52 0.2(3) . . . . ?
C35 C36 C52 C53 0.5(3) . . . . ?
C36 C52 C53 C33 -0.5(3) . . . . ?
C37 C38 C39 C40 -0.4(3) . . . . ?
C38 C37 C42 C41 -1.1(4) . . . . ?
C38 C39 C40 C41 -0.5(3) . . . . ?
C38 C39 C40 C43 178.29(18) . . . . ?
C39 C40 C41 C42 0.6(3) . . . . ?
C39 C40 C43 N5 -92.2(2) . . . . ?
C39 C40 C43 C32 84.2(2) . . . . ?
C40 C41 C42 C37 0.1(4) . . . . ?
C41 C40 C43 N5 86.6(2) . . . . ?
C41 C40 C43 C32 -97.0(2) . . . . ?
C42 C37 C38 C39 1.2(4) . . . . ?
C43 N5 C31 N4 0.42(19) . . . . ?
C43 N5 C31 C30 179.86(16) . . . . ?
C43 N5 C46 C47 -86.2(2) . . . . ?
C43 N5 C46 C51 97.2(2) . . . . ?
C43 C32 C33 C34 -177.05(17) . . . . ?
C43 C32 C33 C53 5.1(3) . . . . ?
C43 C40 C41 C42 -178.13(19) . . . . ?
C44 C27 C28 C29 -2.1(4) . . . . ?
C45 C30 C31 N4 -4.0(3) . . . . ?
C45 C30 C31 N5 176.7(2) . . . . ?
C46 N5 C31 N4 179.87(15) . . . . ?
C46 N5 C31 C30 -0.7(3) . . . . ?
C46 N5 C43 C32 -179.72(15) . . . . ?
C46 N5 C43 C40 -2.5(2) . . . . ?
C46 C47 C48 C49 0.4(3) . . . . ?
C47 C46 C51 C50 -1.0(3) . . . . ?
C47 C48 C49 C50 -0.8(4) . . . . ?
C48 C49 C50 C51 0.4(3) . . . . ?
C49 C50 C51 C46 0.5(3) . . . . ?
C51 C46 C47 C48 0.5(3) . . . . ?
C53 C33 C34 C35 0.9(3) . . . . ?
C54 C5 C6 N2 176.20(16) . . . . ?
C54 C5 C6 C7 -5.5(3) . . . . ?
C54 C14 C15 C11 -0.8(3) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_230320_6637_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2299929'
loop_
_audit_author_name
_audit_author_address
'Xin Zhao'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-10-09 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;
_audit_creation_date             2023-03-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H18 N2'
_chemical_formula_sum            'C27 H18 N2'
_chemical_formula_weight         370.43
_chemical_absolute_configuration ?
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.6802(5)
_cell_length_b                   12.0602(11)
_cell_length_c                   27.607(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1891.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5460
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      56.93
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.858
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0821
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            19750
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.174
_diffrn_reflns_theta_min         2.785
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                3026
_reflns_number_total             3752
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 
;
 Flack x determined using 1010 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3752
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0748
_refine_ls_restrained_S_all      1.112
_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)+(0.1300P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1911
_refine_ls_wR_factor_ref         0.1996
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.053) H9(0.048) H6(0.042) H11(0.036) H12(0.044) H2(0.048)
 H3(0.058) H18(0.058) H17(0.041) H5(0.043) H4(0.056) H8(0.051) H7(0.042)
 H10(0.043) H13(0.04) H16(0.046) H15(0.044) H14(0.038)
 Fixed X: H1(-0.216779) H9(0.100033) H6(0.394443) H11(0.730055) H12(0.992606)
 H2(1.279738) H3(0.474373) H18(0.182544) H17(0.208871) H5(0.829928)
 H4(0.795206) H8(-0.23792) H7(0.055922) H10(1.290279) H13(1.295087)
 H16(1.271374) H15(0.967209) H14(0.68515)
 Fixed Y: H1(0.465489) H9(0.345679) H6(0.38203) H11(0.340045) H12(0.292091)
 H2(0.419629) H3(0.051949) H18(0.156339) H17(0.348915) H5(0.333889)
 H4(0.140102) H8(0.627187) H7(0.665785) H10(0.595572) H13(0.754628)
 H16(0.936735) H15(0.990224) H14(0.862968)
 Fixed Z: H1(0.208528) H9(0.217203) H6(0.274283) H11(0.444303) H12(0.505113)
 H2(0.530033) H3(0.359538) H18(0.39679) H17(0.398268) H5(0.326909) H4(0.322957)
 H8(0.254752) H7(0.31182) H10(0.497952) H13(0.4692) H16(0.441348) H15(0.389311)
 H14(0.364983)
;
_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
N1 N 0.5419(6) 0.4768(3) 0.36566(11) 0.0257(8) Uani 1 1 d . . . . .
N2 N 0.5037(6) 0.6570(3) 0.34580(12) 0.0283(8) Uani 1 1 d . . . . .
C1 C -0.0965(9) 0.4818(4) 0.23134(17) 0.0442(13) Uani 1 1 d . . . . .
H1 H -0.216779 0.465489 0.208528 0.053 Uiso 1 1 calc R U . . .
C2 C 0.0906(9) 0.4103(4) 0.23678(16) 0.0399(12) Uani 1 1 d . . . . .
H9 H 0.100033 0.345679 0.217203 0.048 Uiso 1 1 calc R U . . .
C3 C 0.2660(9) 0.4318(4) 0.27071(15) 0.0350(11) Uani 1 1 d . . . . .
H6 H 0.394443 0.382030 0.274283 0.042 Uiso 1 1 calc R U . . .
C4 C 0.2524(7) 0.5271(3) 0.29952(14) 0.0270(9) Uani 1 1 d . . . . .
C5 C 0.4316(8) 0.5547(3) 0.33654(15) 0.0267(9) Uani 1 1 d . . . . .
C6 C 0.6944(7) 0.5354(3) 0.39562(14) 0.0257(9) Uani 1 1 d . . . . .
C7 C 0.8492(7) 0.4989(3) 0.43357(14) 0.0257(9) Uani 1 1 d . . . . .
C8 C 0.8436(8) 0.3925(3) 0.45493(14) 0.0304(10) Uani 1 1 d . . . . .
H11 H 0.730055 0.340045 0.444303 0.036 Uiso 1 1 calc R U . . .
C9 C 0.9995(9) 0.3636(4) 0.49080(15) 0.0369(11) Uani 1 1 d . . . . .
H12 H 0.992606 0.292091 0.505113 0.044 Uiso 1 1 calc R U . . .
C10 C 1.1681(9) 0.4403(4) 0.50606(17) 0.0397(12) Uani 1 1 d . . . . .
H2 H 1.279738 0.419629 0.530033 0.048 Uiso 1 1 calc R U . . .
C11 C 0.4861(11) 0.1305(4) 0.36019(18) 0.0485(14) Uani 1 1 d . . . . .
H3 H 0.474373 0.051949 0.359538 0.058 Uiso 1 1 calc R U . . .
C12 C 0.3135(10) 0.1923(4) 0.38227(19) 0.0486(14) Uani 1 1 d . . . . .
H18 H 0.182544 0.156339 0.396790 0.058 Uiso 1 1 calc R U . . .
C13 C 0.3295(8) 0.3062(4) 0.38344(15) 0.0342(11) Uani 1 1 d . . . . .
H17 H 0.208871 0.348915 0.398268 0.041 Uiso 1 1 calc R U . . .
C14 C 0.5220(8) 0.3580(3) 0.36293(13) 0.0259(9) Uani 1 1 d . . . . .
C15 C 0.6975(9) 0.2976(4) 0.34072(15) 0.0360(11) Uani 1 1 d . . . . .
H5 H 0.829928 0.333889 0.326909 0.043 Uiso 1 1 calc R U . . .
C16 C 0.6777(10) 0.1828(4) 0.33884(17) 0.0463(13) Uani 1 1 d . . . . .
H4 H 0.795206 0.140102 0.322957 0.056 Uiso 1 1 calc R U . . .
C17 C -0.1101(8) 0.5773(5) 0.25895(18) 0.0428(12) Uani 1 1 d . . . . .
H8 H -0.237920 0.627187 0.254752 0.051 Uiso 1 1 calc R U . . .
C18 C 0.0647(8) 0.6000(4) 0.29296(16) 0.0353(11) Uani 1 1 d . . . . .
H7 H 0.055922 0.665785 0.311820 0.042 Uiso 1 1 calc R U . . .
C19 C 0.6699(8) 0.6446(3) 0.38201(13) 0.0259(9) Uani 1 1 d . . . . .
C20 C 1.0131(8) 0.5797(3) 0.45093(15) 0.0285(9) Uani 1 1 d . . . . .
C21 C 1.1742(9) 0.5449(4) 0.48683(16) 0.0358(11) Uani 1 1 d . . . . .
H10 H 1.290279 0.595572 0.497952 0.043 Uiso 1 1 calc R U . . .
C22 C 1.0046(8) 0.6952(3) 0.43307(14) 0.0278(9) Uani 1 1 d . . . . .
C23 C 1.1716(9) 0.7753(3) 0.44781(15) 0.0333(11) Uani 1 1 d . . . . .
H13 H 1.295087 0.754628 0.469200 0.040 Uiso 1 1 calc R U . . .
C24 C 1.1572(9) 0.8839(4) 0.43138(16) 0.0385(12) Uani 1 1 d . . . . .
H16 H 1.271374 0.936735 0.441348 0.046 Uiso 1 1 calc R U . . .
C25 C 0.9760(9) 0.9157(3) 0.40032(16) 0.0367(11) Uani 1 1 d . . . . .
H15 H 0.967209 0.990224 0.389311 0.044 Uiso 1 1 calc R U . . .
C26 C 0.8103(8) 0.8403(3) 0.38555(14) 0.0313(10) Uani 1 1 d . . . . .
H14 H 0.685150 0.862968 0.364983 0.038 Uiso 1 1 calc R U . . .
C27 C 0.8260(8) 0.7291(3) 0.40092(14) 0.0263(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.386(5) . ?
N1 C6 1.391(5) . ?
N1 C14 1.440(5) . ?
N2 C5 1.325(5) . ?
N2 C19 1.383(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.377(7) . ?
C1 C17 1.383(7) . ?
C2 H9 0.9500 . ?
C2 C3 1.392(6) . ?
C3 H6 0.9500 . ?
C3 C4 1.399(6) . ?
C4 C5 1.480(6) . ?
C4 C18 1.394(6) . ?
C6 C7 1.437(6) . ?
C6 C19 1.377(6) . ?
C7 C8 1.413(6) . ?
C7 C20 1.430(6) . ?
C8 H11 0.9500 . ?
C8 C9 1.373(6) . ?
C9 H12 0.9500 . ?
C9 C10 1.396(7) . ?
C10 H2 0.9500 . ?
C10 C21 1.369(7) . ?
C11 H3 0.9500 . ?
C11 C12 1.374(7) . ?
C11 C16 1.389(8) . ?
C12 H18 0.9500 . ?
C12 C13 1.377(6) . ?
C13 H17 0.9500 . ?
C13 C14 1.380(6) . ?
C14 C15 1.379(6) . ?
C15 H5 0.9500 . ?
C15 C16 1.390(7) . ?
C16 H4 0.9500 . ?
C17 H8 0.9500 . ?
C17 C18 1.394(7) . ?
C18 H7 0.9500 . ?
C19 C27 1.448(6) . ?
C20 C21 1.413(6) . ?
C20 C22 1.479(6) . ?
C21 H10 0.9500 . ?
C22 C23 1.414(6) . ?
C22 C27 1.409(6) . ?
C23 H13 0.9500 . ?
C23 C24 1.388(6) . ?
C24 H16 0.9500 . ?
C24 C25 1.393(7) . ?
C25 H15 0.9500 . ?
C25 C26 1.371(6) . ?
C26 H14 0.9500 . ?
C26 C27 1.409(6) . ?

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
C5 N1 C6 106.4(3) . . ?
C5 N1 C14 127.5(3) . . ?
C6 N1 C14 125.9(3) . . ?
C5 N2 C19 104.5(3) . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C17 120.3(4) . . ?
C17 C1 H1 119.8 . . ?
C1 C2 H9 119.7 . . ?
C1 C2 C3 120.6(4) . . ?
C3 C2 H9 119.7 . . ?
C2 C3 H6 120.1 . . ?
C2 C3 C4 119.7(4) . . ?
C4 C3 H6 120.1 . . ?
C3 C4 C5 122.7(4) . . ?
C18 C4 C3 119.1(4) . . ?
C18 C4 C5 118.2(4) . . ?
N1 C5 C4 124.0(4) . . ?
N2 C5 N1 112.3(4) . . ?
N2 C5 C4 123.8(4) . . ?
N1 C6 C7 131.2(4) . . ?
C19 C6 N1 105.1(4) . . ?
C19 C6 C7 123.7(4) . . ?
C8 C7 C6 124.7(4) . . ?
C8 C7 C20 119.6(4) . . ?
C20 C7 C6 115.7(4) . . ?
C7 C8 H11 119.4 . . ?
C9 C8 C7 121.1(4) . . ?
C9 C8 H11 119.4 . . ?
C8 C9 H12 120.3 . . ?
C8 C9 C10 119.5(4) . . ?
C10 C9 H12 120.3 . . ?
C9 C10 H2 119.7 . . ?
C21 C10 C9 120.7(4) . . ?
C21 C10 H2 119.7 . . ?
C12 C11 H3 120.0 . . ?
C12 C11 C16 120.1(4) . . ?
C16 C11 H3 120.0 . . ?
C11 C12 H18 119.9 . . ?
C11 C12 C13 120.3(5) . . ?
C13 C12 H18 119.9 . . ?
C12 C13 H17 120.2 . . ?
C12 C13 C14 119.6(5) . . ?
C14 C13 H17 120.2 . . ?
C13 C14 N1 119.4(4) . . ?
C15 C14 N1 119.5(4) . . ?
C15 C14 C13 121.1(4) . . ?
C14 C15 H5 120.5 . . ?
C14 C15 C16 119.0(5) . . ?
C16 C15 H5 120.5 . . ?
C11 C16 C15 120.0(5) . . ?
C11 C16 H4 120.0 . . ?
C15 C16 H4 120.0 . . ?
C1 C17 H8 120.2 . . ?
C1 C17 C18 119.7(5) . . ?
C18 C17 H8 120.2 . . ?
C4 C18 H7 119.7 . . ?
C17 C18 C4 120.5(4) . . ?
C17 C18 H7 119.7 . . ?
N2 C19 C27 127.1(4) . . ?
C6 C19 N2 111.7(4) . . ?
C6 C19 C27 120.8(4) . . ?
C7 C20 C22 120.6(4) . . ?
C21 C20 C7 117.0(4) . . ?
C21 C20 C22 122.3(4) . . ?
C10 C21 C20 121.9(4) . . ?
C10 C21 H10 119.0 . . ?
C20 C21 H10 119.0 . . ?
C23 C22 C20 121.7(4) . . ?
C27 C22 C20 120.5(4) . . ?
C27 C22 C23 117.8(4) . . ?
C22 C23 H13 119.6 . . ?
C24 C23 C22 120.7(4) . . ?
C24 C23 H13 119.6 . . ?
C23 C24 H16 119.9 . . ?
C23 C24 C25 120.3(4) . . ?
C25 C24 H16 119.9 . . ?
C24 C25 H15 119.8 . . ?
C26 C25 C24 120.5(4) . . ?
C26 C25 H15 119.8 . . ?
C25 C26 H14 120.1 . . ?
C25 C26 C27 119.9(4) . . ?
C27 C26 H14 120.1 . . ?
C22 C27 C19 117.6(4) . . ?
C22 C27 C26 120.8(4) . . ?
C26 C27 C19 121.5(4) . . ?

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
N1 C6 C7 C8 -13.1(7) . . . . ?
N1 C6 C7 C20 168.9(4) . . . . ?
N1 C6 C19 N2 1.7(5) . . . . ?
N1 C6 C19 C27 -171.5(3) . . . . ?
N1 C14 C15 C16 179.2(4) . . . . ?
N2 C19 C27 C22 -171.3(4) . . . . ?
N2 C19 C27 C26 4.8(6) . . . . ?
C1 C2 C3 C4 -0.1(7) . . . . ?
C1 C17 C18 C4 -0.3(7) . . . . ?
C2 C1 C17 C18 -1.1(7) . . . . ?
C2 C3 C4 C5 179.5(4) . . . . ?
C2 C3 C4 C18 -1.3(6) . . . . ?
C3 C4 C5 N1 -37.7(6) . . . . ?
C3 C4 C5 N2 142.7(4) . . . . ?
C3 C4 C18 C17 1.5(6) . . . . ?
C5 N1 C6 C7 178.4(4) . . . . ?
C5 N1 C6 C19 -1.2(4) . . . . ?
C5 N1 C14 C13 -80.6(5) . . . . ?
C5 N1 C14 C15 100.6(5) . . . . ?
C5 N2 C19 C6 -1.6(5) . . . . ?
C5 N2 C19 C27 171.1(4) . . . . ?
C5 C4 C18 C17 -179.3(4) . . . . ?
C6 N1 C5 N2 0.3(5) . . . . ?
C6 N1 C5 C4 -179.4(4) . . . . ?
C6 N1 C14 C13 105.7(5) . . . . ?
C6 N1 C14 C15 -73.0(5) . . . . ?
C6 C7 C8 C9 179.4(4) . . . . ?
C6 C7 C20 C21 -177.4(4) . . . . ?
C6 C7 C20 C22 5.0(6) . . . . ?
C6 C19 C27 C22 0.8(6) . . . . ?
C6 C19 C27 C26 176.9(4) . . . . ?
C7 C6 C19 N2 -177.9(4) . . . . ?
C7 C6 C19 C27 8.9(6) . . . . ?
C7 C8 C9 C10 -0.7(7) . . . . ?
C7 C20 C21 C10 -3.1(7) . . . . ?
C7 C20 C22 C23 -176.8(4) . . . . ?
C7 C20 C22 C27 3.9(6) . . . . ?
C8 C7 C20 C21 4.5(6) . . . . ?
C8 C7 C20 C22 -173.1(4) . . . . ?
C8 C9 C10 C21 2.3(7) . . . . ?
C9 C10 C21 C20 -0.3(7) . . . . ?
C11 C12 C13 C14 -1.0(7) . . . . ?
C12 C11 C16 C15 1.4(7) . . . . ?
C12 C13 C14 N1 -177.9(4) . . . . ?
C12 C13 C14 C15 0.8(7) . . . . ?
C13 C14 C15 C16 0.5(7) . . . . ?
C14 N1 C5 N2 -174.4(4) . . . . ?
C14 N1 C5 C4 6.0(6) . . . . ?
C14 N1 C6 C7 -6.8(7) . . . . ?
C14 N1 C6 C19 173.6(4) . . . . ?
C14 C15 C16 C11 -1.6(7) . . . . ?
C16 C11 C12 C13 -0.1(8) . . . . ?
C17 C1 C2 C3 1.3(7) . . . . ?
C18 C4 C5 N1 143.1(4) . . . . ?
C18 C4 C5 N2 -36.5(6) . . . . ?
C19 N2 C5 N1 0.7(4) . . . . ?
C19 N2 C5 C4 -179.6(4) . . . . ?
C19 C6 C7 C8 166.4(4) . . . . ?
C19 C6 C7 C20 -11.5(6) . . . . ?
C20 C7 C8 C9 -2.7(6) . . . . ?
C20 C22 C23 C24 -178.6(4) . . . . ?
C20 C22 C27 C19 -6.9(6) . . . . ?
C20 C22 C27 C26 177.0(4) . . . . ?
C21 C20 C22 C23 5.7(6) . . . . ?
C21 C20 C22 C27 -173.5(4) . . . . ?
C22 C20 C21 C10 174.5(4) . . . . ?
C22 C23 C24 C25 0.5(7) . . . . ?
C23 C22 C27 C19 173.8(4) . . . . ?
C23 C22 C27 C26 -2.3(6) . . . . ?
C23 C24 C25 C26 -0.1(7) . . . . ?
C24 C25 C26 C27 -1.5(7) . . . . ?
C25 C26 C27 C19 -173.2(4) . . . . ?
C25 C26 C27 C22 2.7(6) . . . . ?
C27 C22 C23 C24 0.7(6) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_8_a_sq
_database_code_depnum_ccdc_archive 'CCDC 2299930'
loop_
_audit_author_name
_audit_author_address
'Xin Zhao'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-10-09 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H23 I N2'
_chemical_formula_weight         514.38

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'
I I -0.3257 6.8362 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           68
_space_group_name_H-M_alt        'C c c a'
_space_group_name_Hall           '-C 2b 2bc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1, -y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'x+1, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x, -y, z-1/2'
'-x-1/2, y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x, y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
'-x, y+1/2, z-1/2'

_cell_length_a                   14.119(2)
_cell_length_b                   22.488(2)
_cell_length_c                   17.2094(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5464.3(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    2110
_cell_measurement_theta_min      3.94
_cell_measurement_theta_max      42.78

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             2064
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    9.308
_shelx_estimated_absorpt_T_min   0.401
_shelx_estimated_absorpt_T_max   0.523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19916
_diffrn_reflns_av_unetI/netI     0.0799
_diffrn_reflns_av_R_equivalents  0.1037
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.502
_diffrn_reflns_theta_max         66.455
_diffrn_reflns_theta_full        66.455
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2408
_reflns_number_gt                1016
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²+50.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00027(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2408
_refine_ls_number_parameters     119
_refine_ls_number_restraints     134
_refine_ls_R_factor_all          0.1628
_refine_ls_R_factor_gt           0.1038
_refine_ls_wR_factor_ref         0.2432
_refine_ls_wR_factor_gt          0.2205
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.2500 0.5000 0.1045(10) 0.148(6) Uani 1 2 d S TU P . .
H1A H 0.2280 0.5378 0.0859 0.222 Uiso 0.5 1 calc R U P . .
H1B H 0.3131 0.4930 0.0859 0.222 Uiso 0.5 1 calc R U P . .
H1C H 0.2088 0.4691 0.0859 0.222 Uiso 0.5 1 calc R U P . .
C2 C 0.2235(7) 0.5457(5) 0.2343(6) 0.102(2) Uani 1 1 d . U . . .
C3 C 0.1899(6) 0.6038(3) 0.2074(5) 0.118(3) Uani 1 1 d G U . . .
C4 C 0.0953(6) 0.6085(3) 0.1858(6) 0.153(3) Uani 1 1 d G U . . .
H4 H 0.0549 0.5762 0.1917 0.184 Uiso 1 1 calc R U . . .
C5 C 0.0610(5) 0.6616(4) 0.1553(6) 0.170(4) Uani 1 1 d G U . . .
H5 H -0.0022 0.6647 0.1409 0.204 Uiso 1 1 calc R U . . .
C6 C 0.1214(7) 0.7099(3) 0.1464(5) 0.154(3) Uani 1 1 d G U . . .
H6 H 0.0985 0.7454 0.1260 0.185 Uiso 1 1 calc R U . . .
C7 C 0.2159(6) 0.7053(3) 0.1680(5) 0.137(3) Uani 1 1 d G U . . .
H7 H 0.2563 0.7376 0.1620 0.164 Uiso 1 1 calc R U . . .
C8 C 0.2502(5) 0.6522(4) 0.1985(5) 0.124(3) Uani 1 1 d G U . . .
H8 H 0.3135 0.6491 0.2129 0.149 Uiso 1 1 calc R U . . .
I1 I 0.5000 0.56187(6) 0.2500 0.1629(10) Uani 1 2 d S T P . .
C9 C 0.2086(7) 0.5631(4) 0.3751(4) 0.138(3) Uani 1 1 d G U . . .
C10 C 0.1234(7) 0.5497(4) 0.4117(6) 0.174(4) Uani 1 1 d G U . A .
H10 H 0.0855 0.5191 0.3927 0.209 Uiso 1 1 calc R U . . .
C11 C 0.0949(6) 0.5819(5) 0.4765(6) 0.196(4) Uani 1 1 d G U . A .
H11 H 0.0379 0.5729 0.5009 0.236 Uiso 1 1 calc R U . . .
C12 C 0.1515(8) 0.6276(5) 0.5048(5) 0.190(4) Uani 1 1 d G U . A .
H12 H 0.1325 0.6492 0.5482 0.227 Uiso 1 1 calc R U . . .
C13 C 0.2367(8) 0.6410(4) 0.4683(6) 0.182(4) Uani 1 1 d G U . A .
H13 H 0.2746 0.6716 0.4872 0.219 Uiso 1 1 calc R U . . .
C14 C 0.2652(6) 0.6088(4) 0.4035(5) 0.159(3) Uani 1 1 d G U . A .
H14 H 0.3222 0.6178 0.3790 0.190 Uiso 1 1 calc R U . . .
N1 N 0.2500 0.5000 0.1903(7) 0.104(3) Uani 1 2 d S TU P A .
N2 N 0.2347(7) 0.5285(4) 0.3072(5) 0.112(2) Uani 0.5 1 d . U P A 1
C15 C 0.2347(7) 0.5285(4) 0.3072(5) 0.112(2) Uani 0.5 1 d . 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
C1 N1 1.476(18) . ?
C2 N1 1.330(11) . ?
C2 C15 1.322(12) . ?
C2 N2 1.322(12) . ?
C2 C3 1.467(11) . ?
C3 C4 1.3900 . ?
C3 C8 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C6 C7 1.3900 . ?
C7 C8 1.3900 . ?
C9 C10 1.3900 . ?
C9 C14 1.3900 . ?
C9 C15 1.452(10) . ?
C9 N2 1.452(10) . ?
C10 C11 1.3900 . ?
C11 C12 1.3900 . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
N1 C2 1.330(11) 2_565 ?
N2 N2 1.354(17) 2_565 ?
C15 C15 1.354(17) 2_565 ?

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
N1 C2 C15 106.4(10) . . ?
N1 C2 N2 106.4(10) . . ?
N1 C2 C3 126.9(9) . . ?
C15 C2 C3 126.8(9) . . ?
N2 C2 C3 126.8(9) . . ?
C4 C3 C8 120.0 . . ?
C4 C3 C2 117.6(7) . . ?
C8 C3 C2 122.3(7) . . ?
C3 C4 C5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C5 C6 C7 120.0 . . ?
C8 C7 C6 120.0 . . ?
C7 C8 C3 120.0 . . ?
C10 C9 C14 120.0 . . ?
C10 C9 C15 117.9(9) . . ?
C14 C9 C15 122.1(9) . . ?
C10 C9 N2 117.9(9) . . ?
C14 C9 N2 122.1(9) . . ?
C11 C10 C9 120.0 . . ?
C10 C11 C12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C14 C13 C12 120.0 . . ?
C13 C14 C9 120.0 . . ?
C2 N1 C2 110.6(12) 2_565 . ?
C2 N1 C1 124.7(6) 2_565 . ?
C2 N1 C1 124.7(6) . . ?
C2 N2 N2 108.3(6) . 2_565 ?
C2 N2 C9 125.3(9) . . ?
N2 N2 C9 126.1(5) 2_565 . ?
C2 C15 C15 108.3(6) . 2_565 ?
C2 C15 C9 125.3(9) . . ?
C15 C15 C9 126.1(5) 2_565 . ?

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
N1 C2 C3 C4 81.8(10) . . . . ?
C15 C2 C3 C4 -99.3(11) . . . . ?
N2 C2 C3 C4 -99.3(11) . . . . ?
N1 C2 C3 C8 -94.1(10) . . . . ?
C15 C2 C3 C8 84.8(12) . . . . ?
N2 C2 C3 C8 84.8(12) . . . . ?
C8 C3 C4 C5 0.0 . . . . ?
C2 C3 C4 C5 -176.0(8) . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C6 C7 C8 C3 0.0 . . . . ?
C4 C3 C8 C7 0.0 . . . . ?
C2 C3 C8 C7 175.8(8) . . . . ?
C14 C9 C10 C11 0.0 . . . . ?
C15 C9 C10 C11 -179.4(8) . . . . ?
N2 C9 C10 C11 -179.4(8) . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C9 0.0 . . . . ?
C10 C9 C14 C13 0.0 . . . . ?
C15 C9 C14 C13 179.4(8) . . . . ?
N2 C9 C14 C13 179.4(8) . . . . ?
C15 C2 N1 C2 0.8(6) . . . 2_565 ?
N2 C2 N1 C2 0.8(6) . . . 2_565 ?
C3 C2 N1 C2 179.9(12) . . . 2_565 ?
C15 C2 N1 C1 -179.2(6) . . . . ?
N2 C2 N1 C1 -179.2(6) . . . . ?
C3 C2 N1 C1 -0.1(12) . . . . ?
N1 C2 N2 N2 -2.1(14) . . . 2_565 ?
C3 C2 N2 N2 178.9(11) . . . 2_565 ?
N1 C2 N2 C9 -175.8(9) . . . . ?
C3 C2 N2 C9 5.2(18) . . . . ?
C10 C9 N2 C2 99.4(12) . . . . ?
C14 C9 N2 C2 -80.0(12) . . . . ?
C10 C9 N2 N2 -73.2(15) . . . 2_565 ?
C14 C9 N2 N2 107.4(15) . . . 2_565 ?
N1 C2 C15 C15 -2.1(14) . . . 2_565 ?
C3 C2 C15 C15 178.9(11) . . . 2_565 ?
N1 C2 C15 C9 -175.8(9) . . . . ?
C3 C2 C15 C9 5.2(18) . . . . ?
C10 C9 C15 C2 99.4(12) . . . . ?
C14 C9 C15 C2 -80.0(12) . . . . ?
C10 C9 C15 C15 -73.2(15) . . . 2_565 ?
C14 C9 C15 C15 107.4(15) . . . 2_565 ?

_refine_diff_density_max         0.703
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.090




####################################################################### 
# 
# 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_test
_database_code_depnum_ccdc_archive 'CCDC 2301028'
loop_
_audit_author_name
_audit_author_address
'Xin Zhao'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-10-13 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;
_audit_creation_date             2023-09-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H21 N2, B F4'
_chemical_formula_sum            'C28 H21 B F4 N2'
_chemical_formula_weight         472.28
_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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   8.6240(2)
_cell_length_b                   8.8580(2)
_cell_length_c                   15.8890(3)
_cell_angle_alpha                94.467(2)
_cell_angle_beta                 97.877(2)
_cell_angle_gamma                106.818(2)
_cell_volume                     1142.03(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7890
_cell_measurement_temperature    302.15
_cell_measurement_theta_max      99
_cell_measurement_theta_min      3
_shelx_estimated_absorpt_T_max   0.904
_shelx_estimated_absorpt_T_min   0.814
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       clear_block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21896
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.323
_diffrn_reflns_theta_min         2.829
_diffrn_ambient_temperature      302.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3996
_reflns_number_total             4628
_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 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0092(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         4628
_refine_ls_number_restraints     70
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0521
_refine_ls_restrained_S_all      1.151
_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)+(0.0881P)²+0.2158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1553
_refine_ls_wR_factor_ref         0.1619
_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. Restrained distances
 F2-F5 \\sim F2A-F5A
 with sigma of 0.04
 F1-B3 \\sim F1A-B3A
 with sigma of 0.02
 F2-B3 \\sim F2A-B3A
 with sigma of 0.02
 B3-F4 \\sim B3A-F4A
 with sigma of 0.02
 B3-F5 \\sim B3A-F5A
 with sigma of 0.02
 F2-F4 \\sim F2A-F4A
 with sigma of 0.04
 F4-F5 \\sim F4A-F5A
 with sigma of 0.04
 F1-F2 \\sim F1A-F2A
 with sigma of 0.04
 F1-F4 \\sim F1A-F4A
 with sigma of 0.04
 F1-F5 \\sim F1A-F5A
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 F2A, F1A, B3A, F4A, F5A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F5, F1, B3, F2, F4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(F1A)=Sof(B3A)=Sof(F2A)=Sof(F4A)=Sof(F5A)=Sof(H2B)=Sof(C9)=Sof(H9)=Sof(C8)=
 Sof(H8)=Sof(C7)=Sof(H7)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(B3)=Sof(F4)=Sof(F5)=Sof(C5)=Sof(H5)=Sof(H2A)=Sof(C4)=
 Sof(H4)=Sof(C6)=Sof(H6)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00N(H00N), C00Q(H00Q), C00S(H00S), C00T(H00T),
 C00U(H00U), C3(H3), C5(H5), C2(H2A), C2(H2B), C4(H4), C6(H6), C9(H9), C8(H8),
 C7(H7)
5.b Idealised Me refined as rotating group:
 C00M(H00A,H00B,H00C)
;
_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 0.15262(14) 0.69876(14) 0.68171(8) 0.0469(3) Uani 1 1 d . . . . .
N002 N 0.23689(15) 0.51242(15) 0.73587(8) 0.0491(3) Uani 1 1 d . . . . .
C003 C 0.19552(16) 0.61531(16) 0.61502(9) 0.0445(3) Uani 1 1 d . . . . .
C004 C 0.29870(17) 0.38286(17) 0.59984(10) 0.0474(3) Uani 1 1 d . . . . .
C005 C 0.24800(17) 0.49762(17) 0.64942(9) 0.0453(3) Uani 1 1 d . . . . .
C006 C 0.19041(16) 0.63650(16) 0.52617(9) 0.0462(3) Uani 1 1 d . . . . .
C007 C 0.24063(16) 0.52626(18) 0.47489(9) 0.0485(4) Uani 1 1 d . . . . .
C008 C 0.29253(16) 0.39843(17) 0.51162(10) 0.0489(4) Uani 1 1 d . . . . .
C009 C 0.17896(18) 0.63468(18) 0.75352(9) 0.0495(3) Uani 1 1 d . . . . .
C00B C 0.2816(2) 0.41807(19) 0.79996(10) 0.0538(4) Uani 1 1 d . . . . .
C00D C 0.33887(19) 0.2868(2) 0.46061(11) 0.0593(4) Uani 1 1 d . . . . .
H00D H 0.336215 0.294557 0.402424 0.071 Uiso 1 1 calc R U . . .
C00E C 0.3513(2) 0.25996(19) 0.63343(12) 0.0573(4) Uani 1 1 d . . . . .
H00E H 0.356142 0.250580 0.691556 0.069 Uiso 1 1 calc R U . . .
C00F C 0.1426(2) 0.75784(19) 0.48826(11) 0.0564(4) Uani 1 1 d . . . . .
H00F H 0.108318 0.829447 0.521335 0.068 Uiso 1 1 calc R U . . .
C00G C 0.2409(2) 0.5453(2) 0.38790(10) 0.0592(4) Uani 1 1 d . . . . .
H00G H 0.272376 0.473870 0.353168 0.071 Uiso 1 1 calc R U . . .
C00H C 0.1962(2) 0.6659(2) 0.35282(11) 0.0653(5) Uani 1 1 d . . . . .
H00H H 0.199698 0.676722 0.295300 0.078 Uiso 1 1 calc R U . . .
C00I C 0.1458(2) 0.7719(2) 0.40288(12) 0.0645(4) Uani 1 1 d . . . . .
H00I H 0.114089 0.852901 0.378688 0.077 Uiso 1 1 calc R U . . .
C00J C 0.1662(2) 0.2828(2) 0.81412(12) 0.0665(5) Uani 1 1 d . . . . .
H00J H 0.059563 0.253197 0.783836 0.080 Uiso 1 1 calc R U . . .
C00K C 0.3953(2) 0.1539(2) 0.58133(14) 0.0643(5) Uani 1 1 d . . . . .
H00K H 0.430214 0.073438 0.604127 0.077 Uiso 1 1 calc R U . . .
C00M C 0.0929(2) 0.8377(2) 0.67909(12) 0.0636(4) Uani 1 1 d . . . . .
H00A H 0.174268 0.924136 0.662318 0.095 Uiso 1 1 calc R U . . .
H00B H 0.072346 0.868333 0.734791 0.095 Uiso 1 1 calc R U . . .
H00C H -0.006994 0.811646 0.638457 0.095 Uiso 1 1 calc R U . . .
C00N C 0.3877(2) 0.1672(2) 0.49453(13) 0.0658(5) Uani 1 1 d . . . . .
H00N H 0.415913 0.094351 0.459116 0.079 Uiso 1 1 calc R U . . .
C00Q C 0.4397(2) 0.4650(2) 0.84417(14) 0.0767(6) Uani 1 1 d . . . . .
H00Q H 0.516803 0.556253 0.833567 0.092 Uiso 1 1 calc R U . . .
C00S C 0.2108(3) 0.1919(3) 0.87381(14) 0.0815(6) Uani 1 1 d . . . . .
H00S H 0.134628 0.098932 0.883247 0.098 Uiso 1 1 calc R U . . .
C00T C 0.3672(4) 0.2379(3) 0.91933(17) 0.0973(8) Uani 1 1 d . . . . .
H00T H 0.396297 0.177130 0.960311 0.117 Uiso 1 1 calc R U . . .
C00U C 0.4811(3) 0.3736(3) 0.90461(18) 0.1033(9) Uani 1 1 d . . . . .
H00U H 0.587063 0.404056 0.935698 0.124 Uiso 1 1 calc R U . . .
F1 F 0.6600(8) 0.9112(8) 0.8553(3) 0.157(2) Uani 0.687(4) 1 d D . P A 1
F2 F 0.8000(6) 1.0023(5) 0.7572(4) 0.1546(19) Uani 0.687(4) 1 d D . P A 1
B3 B 0.6643(9) 0.8962(6) 0.7725(5) 0.0782(12) Uani 0.687(4) 1 d D . P A 1
F4 F 0.6721(6) 0.7494(3) 0.74832(18) 0.1504(15) Uani 0.687(4) 1 d D . P A 1
F5 F 0.5313(7) 0.9204(7) 0.7240(4) 0.175(2) Uani 0.687(4) 1 d D . P A 1
F1A F 0.7935(12) 0.9278(17) 0.7434(8) 0.168(4) Uani 0.313(4) 1 d D . P A 2
B3A B 0.6656(16) 0.9339(12) 0.7758(10) 0.068(2) Uani 0.313(4) 1 d D . P A 2
F2A F 0.6799(15) 1.0850(7) 0.7952(5) 0.189(4) Uani 0.313(4) 1 d D . P A 2
F4A F 0.5323(11) 0.8485(17) 0.7245(6) 0.167(5) Uani 0.313(4) 1 d D . P A 2
F5A F 0.6484(11) 0.8766(12) 0.8554(6) 0.096(2) Uani 0.313(4) 1 d D . P A 2
C1 C 0.1501(2) 0.6871(2) 0.83872(10) 0.0557(4) Uani 1 1 d . . . . .
C3 C 0.2755(2) 0.7803(3) 0.89886(12) 0.0714(5) Uani 1 1 d . . . . .
H3 H 0.381316 0.811606 0.886057 0.086 Uiso 1 1 calc R U . . .
C5 C -0.0101(4) 0.6722(5) 0.8506(2) 0.0775(10) Uani 0.687(4) 1 d . . P A 1
H5 H -0.097339 0.627685 0.805879 0.093 Uiso 0.687(4) 1 calc R U P A 1
C2 C 0.2487(3) 0.8296(3) 0.97871(12) 0.0729(5) Uani 1 1 d . . . . .
H2A H 0.337015 0.882977 1.021435 0.087 Uiso 0.687(4) 1 calc R U P A 1
H2B H 0.322382 0.920827 1.010593 0.087 Uiso 0.313(4) 1 calc R U P A 2
C4 C 0.0939(8) 0.7997(7) 0.9943(3) 0.0773(12) Uani 0.687(4) 1 d . . P A 1
H4 H 0.075119 0.829627 1.048474 0.093 Uiso 0.687(4) 1 calc R U P A 1
C6 C -0.0381(4) 0.7244(6) 0.9295(2) 0.0974(14) Uani 0.687(4) 1 d . . P A 1
H6 H -0.145119 0.709122 0.939413 0.117 Uiso 0.687(4) 1 calc R U P A 1
C9 C 0.0239(9) 0.5834(9) 0.8774(5) 0.074(2) Uani 0.313(4) 1 d . . P A 2
H9 H -0.046496 0.489673 0.846195 0.089 Uiso 0.313(4) 1 calc R U P A 2
C8 C 0.0088(11) 0.6248(11) 0.9614(5) 0.089(3) Uani 0.313(4) 1 d . . P A 2
H8 H -0.080358 0.564675 0.983575 0.107 Uiso 0.313(4) 1 calc R U P A 2
C7 C 0.1185(18) 0.7483(14) 1.0110(8) 0.075(3) Uani 0.313(4) 1 d . . P A 2
H7 H 0.104989 0.777106 1.066457 0.090 Uiso 0.313(4) 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 C003 1.3963(17) . ?
N001 C009 1.334(2) . ?
N001 C00M 1.467(2) . ?
N002 C005 1.3887(18) . ?
N002 C009 1.3436(19) . ?
N002 C00B 1.447(2) . ?
C003 C005 1.373(2) . ?
C003 C006 1.435(2) . ?
C004 C005 1.4394(19) . ?
C004 C008 1.414(2) . ?
C004 C00E 1.409(2) . ?
C006 C007 1.422(2) . ?
C006 C00F 1.406(2) . ?
C007 C008 1.465(2) . ?
C007 C00G 1.406(2) . ?
C008 C00D 1.410(2) . ?
C009 C1 1.474(2) . ?
C00B C00J 1.375(3) . ?
C00B C00Q 1.375(2) . ?
C00D H00D 0.9300 . ?
C00D C00N 1.369(3) . ?
C00E H00E 0.9300 . ?
C00E C00K 1.372(2) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.375(2) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.368(3) . ?
C00H H00H 0.9300 . ?
C00H C00I 1.385(3) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00J C00S 1.377(3) . ?
C00K H00K 0.9300 . ?
C00K C00N 1.387(3) . ?
C00M H00A 0.9600 . ?
C00M H00B 0.9600 . ?
C00M H00C 0.9600 . ?
C00N H00N 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00Q C00U 1.378(3) . ?
C00S H00S 0.9300 . ?
C00S C00T 1.370(4) . ?
C00T H00T 0.9300 . ?
C00T C00U 1.374(4) . ?
C00U H00U 0.9300 . ?
F1 B3 1.319(9) . ?
F2 B3 1.337(7) . ?
B3 F4 1.349(6) . ?
B3 F5 1.373(10) . ?
F1A B3A 1.292(15) . ?
B3A F2A 1.316(11) . ?
B3A F4A 1.305(14) . ?
B3A F5A 1.409(17) . ?
C1 C3 1.357(2) . ?
C1 C5 1.390(3) . ?
C1 C9 1.449(7) . ?
C3 H3 0.9300 . ?
C3 C2 1.381(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(4) . ?
C2 H2A 0.9300 . ?
C2 H2B 0.9300 . ?
C2 C4 1.345(6) . ?
C2 C7 1.338(14) . ?
C4 H4 0.9300 . ?
C4 C6 1.390(7) . ?
C6 H6 0.9300 . ?
C9 H9 0.9300 . ?
C9 C8 1.391(9) . ?
C8 H8 0.9300 . ?
C8 C7 1.333(16) . ?
C7 H7 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
C003 N001 C00M 128.39(13) . . ?
C009 N001 C003 108.85(12) . . ?
C009 N001 C00M 122.73(13) . . ?
C005 N002 C00B 127.89(12) . . ?
C009 N002 C005 108.86(13) . . ?
C009 N002 C00B 123.24(13) . . ?
N001 C003 C006 130.86(13) . . ?
C005 C003 N001 106.70(12) . . ?
C005 C003 C006 122.44(13) . . ?
C008 C004 C005 115.72(14) . . ?
C00E C004 C005 124.47(15) . . ?
C00E C004 C008 119.81(14) . . ?
N002 C005 C004 129.74(14) . . ?
C003 C005 N002 106.85(12) . . ?
C003 C005 C004 123.39(13) . . ?
C007 C006 C003 116.02(13) . . ?
C00F C006 C003 124.74(14) . . ?
C00F C006 C007 119.23(14) . . ?
C006 C007 C008 121.22(14) . . ?
C00G C007 C006 117.71(15) . . ?
C00G C007 C008 121.06(14) . . ?
C004 C008 C007 121.17(13) . . ?
C00D C008 C004 117.45(15) . . ?
C00D C008 C007 121.38(15) . . ?
N001 C009 N002 108.74(13) . . ?
N001 C009 C1 126.47(14) . . ?
N002 C009 C1 124.80(15) . . ?
C00J C00B N002 119.39(15) . . ?
C00Q C00B N002 118.91(16) . . ?
C00Q C00B C00J 121.69(17) . . ?
C008 C00D H00D 119.2 . . ?
C00N C00D C008 121.67(17) . . ?
C00N C00D H00D 119.2 . . ?
C004 C00E H00E 119.6 . . ?
C00K C00E C004 120.73(17) . . ?
C00K C00E H00E 119.6 . . ?
C006 C00F H00F 119.6 . . ?
C00I C00F C006 120.82(16) . . ?
C00I C00F H00F 119.6 . . ?
C007 C00G H00G 119.0 . . ?
C00H C00G C007 121.93(16) . . ?
C00H C00G H00G 119.0 . . ?
C00G C00H H00H 120.0 . . ?
C00G C00H C00I 120.08(16) . . ?
C00I C00H H00H 120.0 . . ?
C00F C00I C00H 120.21(17) . . ?
C00F C00I H00I 119.9 . . ?
C00H C00I H00I 119.9 . . ?
C00B C00J H00J 120.5 . . ?
C00B C00J C00S 118.98(18) . . ?
C00S C00J H00J 120.5 . . ?
C00E C00K H00K 120.1 . . ?
C00E C00K C00N 119.80(17) . . ?
C00N C00K H00K 120.1 . . ?
N001 C00M H00A 109.5 . . ?
N001 C00M H00B 109.5 . . ?
N001 C00M H00C 109.5 . . ?
H00A C00M H00B 109.5 . . ?
H00A C00M H00C 109.5 . . ?
H00B C00M H00C 109.5 . . ?
C00D C00N C00K 120.53(15) . . ?
C00D C00N H00N 119.7 . . ?
C00K C00N H00N 119.7 . . ?
C00B C00Q H00Q 120.8 . . ?
C00B C00Q C00U 118.4(2) . . ?
C00U C00Q H00Q 120.8 . . ?
C00J C00S H00S 119.9 . . ?
C00T C00S C00J 120.2(2) . . ?
C00T C00S H00S 119.9 . . ?
C00S C00T H00T 119.9 . . ?
C00S C00T C00U 120.2(2) . . ?
C00U C00T H00T 119.9 . . ?
C00Q C00U H00U 119.7 . . ?
C00T C00U C00Q 120.6(2) . . ?
C00T C00U H00U 119.7 . . ?
F1 B3 F2 109.2(6) . . ?
F1 B3 F4 108.9(7) . . ?
F1 B3 F5 113.0(7) . . ?
F2 B3 F4 108.1(6) . . ?
F2 B3 F5 108.0(7) . . ?
F4 B3 F5 109.6(6) . . ?
F1A B3A F2A 107.2(11) . . ?
F1A B3A F4A 110.0(13) . . ?
F1A B3A F5A 117.6(13) . . ?
F2A B3A F5A 101.4(11) . . ?
F4A B3A F2A 116.6(14) . . ?
F4A B3A F5A 104.3(10) . . ?
C3 C1 C009 121.10(15) . . ?
C3 C1 C5 118.49(19) . . ?
C3 C1 C9 111.5(3) . . ?
C5 C1 C009 118.72(18) . . ?
C9 C1 C009 119.6(3) . . ?
C1 C3 H3 119.4 . . ?
C1 C3 C2 121.18(18) . . ?
C2 C3 H3 119.4 . . ?
C1 C5 H5 120.4 . . ?
C6 C5 C1 119.2(3) . . ?
C6 C5 H5 120.4 . . ?
C3 C2 H2A 120.2 . . ?
C3 C2 H2B 119.4 . . ?
C4 C2 C3 119.5(3) . . ?
C4 C2 H2A 120.2 . . ?
C7 C2 C3 121.1(6) . . ?
C7 C2 H2B 119.4 . . ?
C2 C4 H4 119.9 . . ?
C2 C4 C6 120.1(4) . . ?
C6 C4 H4 119.9 . . ?
C5 C6 C4 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C4 C6 H6 120.1 . . ?
C1 C9 H9 120.2 . . ?
C8 C9 C1 119.6(6) . . ?
C8 C9 H9 120.2 . . ?
C9 C8 H8 119.1 . . ?
C7 C8 C9 121.8(8) . . ?
C7 C8 H8 119.1 . . ?
C2 C7 H7 121.0 . . ?
C8 C7 C2 118.0(9) . . ?
C8 C7 H7 121.0 . . ?

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 C003 C005 N002 -0.33(15) . . . . ?
N001 C003 C005 C004 178.20(12) . . . . ?
N001 C003 C006 C007 -178.67(13) . . . . ?
N001 C003 C006 C00F 2.4(2) . . . . ?
N001 C009 C1 C3 -99.4(2) . . . . ?
N001 C009 C1 C5 65.6(3) . . . . ?
N001 C009 C1 C9 114.0(5) . . . . ?
N002 C009 C1 C3 80.6(2) . . . . ?
N002 C009 C1 C5 -114.4(3) . . . . ?
N002 C009 C1 C9 -65.9(5) . . . . ?
N002 C00B C00J C00S 178.53(17) . . . . ?
N002 C00B C00Q C00U -179.5(2) . . . . ?
C003 N001 C009 N002 -0.19(16) . . . . ?
C003 N001 C009 C1 179.86(14) . . . . ?
C003 C006 C007 C008 0.59(19) . . . . ?
C003 C006 C007 C00G -178.58(12) . . . . ?
C003 C006 C00F C00I 178.13(14) . . . . ?
C004 C008 C00D C00N 0.2(2) . . . . ?
C004 C00E C00K C00N -0.2(2) . . . . ?
C005 N002 C009 N001 -0.02(16) . . . . ?
C005 N002 C009 C1 179.93(14) . . . . ?
C005 N002 C00B C00J -89.7(2) . . . . ?
C005 N002 C00B C00Q 89.3(2) . . . . ?
C005 C003 C006 C007 1.0(2) . . . . ?
C005 C003 C006 C00F -177.96(13) . . . . ?
C005 C004 C008 C007 1.20(19) . . . . ?
C005 C004 C008 C00D -179.07(12) . . . . ?
C005 C004 C00E C00K 179.05(14) . . . . ?
C006 C003 C005 N002 179.93(12) . . . . ?
C006 C003 C005 C004 -1.5(2) . . . . ?
C006 C007 C008 C004 -1.7(2) . . . . ?
C006 C007 C008 C00D 178.56(12) . . . . ?
C006 C007 C00G C00H 0.6(2) . . . . ?
C006 C00F C00I C00H 0.1(3) . . . . ?
C007 C006 C00F C00I -0.8(2) . . . . ?
C007 C008 C00D C00N 179.92(13) . . . . ?
C007 C00G C00H C00I -1.3(3) . . . . ?
C008 C004 C005 N002 178.55(13) . . . . ?
C008 C004 C005 C003 0.4(2) . . . . ?
C008 C004 C00E C00K -0.6(2) . . . . ?
C008 C007 C00G C00H -178.59(14) . . . . ?
C008 C00D C00N C00K -1.0(2) . . . . ?
C009 N001 C003 C005 0.33(15) . . . . ?
C009 N001 C003 C006 -179.96(14) . . . . ?
C009 N002 C005 C003 0.23(16) . . . . ?
C009 N002 C005 C004 -178.18(14) . . . . ?
C009 N002 C00B C00J 91.7(2) . . . . ?
C009 N002 C00B C00Q -89.3(2) . . . . ?
C009 C1 C3 C2 179.99(18) . . . . ?
C009 C1 C5 C6 -178.5(4) . . . . ?
C009 C1 C9 C8 172.9(7) . . . . ?
C00B N002 C005 C003 -178.52(13) . . . . ?
C00B N002 C005 C004 3.1(2) . . . . ?
C00B N002 C009 N001 178.80(13) . . . . ?
C00B N002 C009 C1 -1.3(2) . . . . ?
C00B C00J C00S C00T 1.3(3) . . . . ?
C00B C00Q C00U C00T 0.8(4) . . . . ?
C00E C004 C005 N002 -1.1(2) . . . . ?
C00E C004 C005 C003 -179.26(13) . . . . ?
C00E C004 C008 C007 -179.14(12) . . . . ?
C00E C004 C008 C00D 0.6(2) . . . . ?
C00E C00K C00N C00D 1.0(3) . . . . ?
C00F C006 C007 C008 179.61(12) . . . . ?
C00F C006 C007 C00G 0.4(2) . . . . ?
C00G C007 C008 C004 177.42(13) . . . . ?
C00G C007 C008 C00D -2.3(2) . . . . ?
C00G C00H C00I C00F 0.9(3) . . . . ?
C00J C00B C00Q C00U -0.6(3) . . . . ?
C00J C00S C00T C00U -1.1(4) . . . . ?
C00M N001 C003 C005 178.46(14) . . . . ?
C00M N001 C003 C006 -1.8(2) . . . . ?
C00M N001 C009 N002 -178.45(13) . . . . ?
C00M N001 C009 C1 1.6(2) . . . . ?
C00Q C00B C00J C00S -0.4(3) . . . . ?
C00S C00T C00U C00Q 0.1(5) . . . . ?
C1 C3 C2 C4 -7.4(4) . . . . ?
C1 C3 C2 C7 23.5(6) . . . . ?
C1 C5 C6 C4 4.0(7) . . . . ?
C1 C9 C8 C7 -7.7(15) . . . . ?
C3 C1 C5 C6 -13.1(5) . . . . ?
C3 C1 C9 C8 23.4(10) . . . . ?
C3 C2 C4 C6 -2.0(6) . . . . ?
C3 C2 C7 C8 -4.8(11) . . . . ?
C5 C1 C3 C2 15.0(4) . . . . ?
C2 C4 C6 C5 3.6(8) . . . . ?
C9 C1 C3 C2 -31.0(5) . . . . ?
C9 C8 C7 C2 -2.3(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2299931'
loop_
_audit_author_name
_audit_author_address
'Xin Zhao'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-10-09 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H21 I N2'
_chemical_formula_weight         512.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   13.712(6)
_cell_length_b                   10.149(4)
_cell_length_c                   16.939(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.859(10)
_cell_angle_gamma                90
_cell_volume                     2267.6(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3944
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      20.10

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.430
_shelx_estimated_absorpt_T_min   0.847
_shelx_estimated_absorpt_T_max   0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33041
_diffrn_reflns_av_unetI/netI     0.1346
_diffrn_reflns_av_R_equivalents  0.1583
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.364
_diffrn_reflns_theta_max         25.166
_diffrn_reflns_theta_full        25.166
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4061
_reflns_number_gt                1774
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0817P)²+4.0299P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0045(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4061
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2095
_refine_ls_R_factor_gt           0.0785
_refine_ls_wR_factor_ref         0.2074
_refine_ls_wR_factor_gt          0.1556
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.5807(8) 0.4486(8) 0.5988(5) 0.059(3) Uani 1 1 d . . . . .
C2 C 0.4818(8) 0.4261(10) 0.6042(5) 0.067(3) Uani 1 1 d . . . . .
H2 H 0.4517 0.4870 0.6312 0.080 Uiso 1 1 calc R U . . .
C3 C 0.4288(8) 0.3162(10) 0.5705(6) 0.072(3) Uani 1 1 d . . . . .
H3 H 0.3625 0.3044 0.5730 0.087 Uiso 1 1 calc R U . . .
C4 C 0.4737(9) 0.2231(10) 0.5328(6) 0.071(3) Uani 1 1 d . . . . .
H4 H 0.4382 0.1476 0.5108 0.085 Uiso 1 1 calc R U . . .
C5 C 0.5704(9) 0.2415(9) 0.5279(5) 0.065(3) Uani 1 1 d . . . . .
H5 H 0.5984 0.1789 0.5004 0.078 Uiso 1 1 calc R U . . .
C6 C 0.6295(8) 0.3505(8) 0.5624(5) 0.056(3) Uani 1 1 d . . . . .
C7 C 0.7336(8) 0.3660(8) 0.5606(5) 0.054(2) Uani 1 1 d . . . . .
C8 C 0.7816(9) 0.2646(9) 0.5284(5) 0.066(3) Uani 1 1 d . . . . .
H8 H 0.7455 0.1885 0.5083 0.079 Uiso 1 1 calc R U . . .
C9 C 0.8800(10) 0.2760(10) 0.5262(6) 0.076(3) Uani 1 1 d . . . . .
H9 H 0.9097 0.2079 0.5042 0.091 Uiso 1 1 calc R U . . .
C10 C 0.9361(8) 0.3867(10) 0.5560(6) 0.069(3) Uani 1 1 d . . . . .
H10 H 1.0031 0.3932 0.5542 0.083 Uiso 1 1 calc R U . . .
C11 C 0.8925(8) 0.4872(9) 0.5883(5) 0.059(2) Uani 1 1 d . . . . .
H11 H 0.9300 0.5623 0.6085 0.071 Uiso 1 1 calc R U . . .
C12 C 0.7922(8) 0.4774(8) 0.5912(5) 0.053(2) Uani 1 1 d . . . . .
C13 C 0.7384(8) 0.5765(8) 0.6264(5) 0.049(2) Uani 1 1 d . . . . .
C14 C 0.6431(8) 0.5613(8) 0.6312(5) 0.049(2) Uani 1 1 d . . . . .
C15 C 0.5271(7) 0.7028(9) 0.6935(6) 0.069(3) Uani 1 1 d . . . . .
H15A H 0.4697 0.7037 0.6459 0.104 Uiso 1 1 calc R U . . .
H15B H 0.5336 0.7873 0.7199 0.104 Uiso 1 1 calc R U . . .
H15C H 0.5176 0.6362 0.7309 0.104 Uiso 1 1 calc R U . . .
C16 C 0.7003(8) 0.7537(8) 0.6875(5) 0.050(2) Uani 1 1 d . . . . .
C17 C 0.7089(7) 0.8821(8) 0.7287(6) 0.056(2) Uani 1 1 d . . . . .
C18 C 0.6642(10) 0.9935(9) 0.6891(6) 0.084(4) Uani 1 1 d . . . . .
H18 H 0.6253 0.9876 0.6349 0.101 Uiso 1 1 calc R U . . .
C19 C 0.6756(9) 1.1133(9) 0.7278(7) 0.084(3) Uani 1 1 d . . . . .
H19 H 0.6461 1.1883 0.6997 0.101 Uiso 1 1 calc R U . . .
C20 C 0.7299(8) 1.1213(9) 0.8067(7) 0.073(3) Uani 1 1 d . . . . .
H20 H 0.7386 1.2030 0.8326 0.087 Uiso 1 1 calc R U . . .
C21 C 0.7729(9) 1.0114(9) 0.8501(6) 0.077(3) Uani 1 1 d . . . . .
H21 H 0.8082 1.0180 0.9053 0.093 Uiso 1 1 calc R U . . .
C22 C 0.7630(7) 0.8917(9) 0.8108(6) 0.066(3) Uani 1 1 d . . . . .
H22 H 0.7926 0.8170 0.8391 0.079 Uiso 1 1 calc R U . . .
C23 C 0.8714(8) 0.7568(8) 0.6700(6) 0.058(3) Uani 1 1 d . . . . .
C24 C 0.8805(10) 0.8427(10) 0.6111(7) 0.082(3) Uani 1 1 d . . . . .
H24 H 0.8256 0.8650 0.5672 0.098 Uiso 1 1 calc R U . . .
C25 C 0.9777(15) 0.8963(11) 0.6198(10) 0.107(5) Uani 1 1 d . . . . .
H25 H 0.9885 0.9560 0.5815 0.128 Uiso 1 1 calc R U . . .
C26 C 1.0561(13) 0.8596(16) 0.6854(13) 0.119(6) Uani 1 1 d . . . . .
H26 H 1.1199 0.8953 0.6903 0.142 Uiso 1 1 calc R U . . .
C27 C 1.0448(10) 0.7744(16) 0.7430(9) 0.105(4) Uani 1 1 d . . . . .
H27 H 1.0996 0.7511 0.7867 0.125 Uiso 1 1 calc R U . . .
C28 C 0.9506(10) 0.7229(10) 0.7356(7) 0.074(3) Uani 1 1 d . . . . .
H28 H 0.9403 0.6650 0.7751 0.088 Uiso 1 1 calc R U . . .
I1 I 0.70934(7) 0.51683(7) 0.87226(5) 0.0986(5) Uani 1 1 d . . . . .
N1 N 0.7727(6) 0.6965(7) 0.6616(4) 0.0513(18) Uani 1 1 d . . . . .
N2 N 0.6190(6) 0.6742(7) 0.6686(4) 0.0546(19) Uani 1 1 d . . . . .


_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 C2 1.403(13) . ?
C1 C6 1.430(12) . ?
C1 C14 1.444(12) . ?
C2 C3 1.368(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.444(12) . ?
C7 C12 1.401(11) . ?
C7 C8 1.409(12) . ?
C8 C9 1.365(13) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(13) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(12) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.468(13) . ?
C13 C14 1.339(11) . ?
C13 N1 1.381(10) . ?
C14 N2 1.393(10) . ?
C15 N2 1.463(10) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N1 1.324(10) . ?
C16 N2 1.342(10) . ?
C16 C17 1.469(12) . ?
C17 C18 1.371(12) . ?
C17 C22 1.388(12) . ?
C18 C19 1.369(13) . ?
C18 H18 0.9300 . ?
C19 C20 1.342(13) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(13) . ?
C20 H20 0.9300 . ?
C21 C22 1.374(12) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.356(13) . ?
C23 C28 1.369(13) . ?
C23 N1 1.456(11) . ?
C24 C25 1.408(17) . ?
C24 H24 0.9300 . ?
C25 C26 1.370(19) . ?
C25 H25 0.9300 . ?
C26 C27 1.344(19) . ?
C26 H26 0.9300 . ?
C27 C28 1.367(16) . ?
C27 H27 0.9300 . ?
C28 H28 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
C2 C1 C6 119.3(9) . . ?
C2 C1 C14 125.9(9) . . ?
C6 C1 C14 114.6(9) . . ?
C3 C2 C1 121.2(10) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.9(10) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.0(9) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 122.9(9) . . ?
C4 C5 H5 118.5 . . ?
C6 C5 H5 118.5 . . ?
C5 C6 C1 116.4(10) . . ?
C5 C6 C7 122.7(9) . . ?
C1 C6 C7 121.0(8) . . ?
C12 C7 C8 116.8(9) . . ?
C12 C7 C6 123.4(8) . . ?
C8 C7 C6 119.8(9) . . ?
C9 C8 C7 121.2(9) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 121.1(9) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 119.6(10) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.2(9) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 121.2(9) . . ?
C11 C12 C13 125.2(8) . . ?
C7 C12 C13 113.7(9) . . ?
C14 C13 N1 107.4(8) . . ?
C14 C13 C12 123.6(8) . . ?
N1 C13 C12 129.0(10) . . ?
C13 C14 N2 106.8(8) . . ?
C13 C14 C1 123.7(9) . . ?
N2 C14 C1 129.4(10) . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 N2 107.9(7) . . ?
N1 C16 C17 125.2(9) . . ?
N2 C16 C17 126.9(9) . . ?
C18 C17 C22 118.5(8) . . ?
C18 C17 C16 122.2(9) . . ?
C22 C17 C16 119.3(8) . . ?
C19 C18 C17 121.3(9) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C20 C19 C18 119.3(9) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 121.5(9) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C22 C21 C20 119.0(9) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C21 C22 C17 120.2(9) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
C24 C23 C28 123.2(10) . . ?
C24 C23 N1 118.0(10) . . ?
C28 C23 N1 118.9(9) . . ?
C23 C24 C25 116.5(12) . . ?
C23 C24 H24 121.8 . . ?
C25 C24 H24 121.8 . . ?
C26 C25 C24 119.4(13) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C27 C26 C25 122.9(15) . . ?
C27 C26 H26 118.5 . . ?
C25 C26 H26 118.5 . . ?
C26 C27 C28 118.2(14) . . ?
C26 C27 H27 120.9 . . ?
C28 C27 H27 120.9 . . ?
C27 C28 C23 119.9(12) . . ?
C27 C28 H28 120.1 . . ?
C23 C28 H28 120.1 . . ?
C16 N1 C13 109.3(8) . . ?
C16 N1 C23 122.9(7) . . ?
C13 N1 C23 127.7(8) . . ?
C16 N2 C14 108.5(7) . . ?
C16 N2 C15 122.5(7) . . ?
C14 N2 C15 128.7(8) . . ?

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
C6 C1 C2 C3 -4.4(13) . . . . ?
C14 C1 C2 C3 179.3(8) . . . . ?
C1 C2 C3 C4 2.2(14) . . . . ?
C2 C3 C4 C5 -1.1(14) . . . . ?
C3 C4 C5 C6 2.4(14) . . . . ?
C4 C5 C6 C1 -4.4(13) . . . . ?
C4 C5 C6 C7 176.7(8) . . . . ?
C2 C1 C6 C5 5.3(11) . . . . ?
C14 C1 C6 C5 -178.0(7) . . . . ?
C2 C1 C6 C7 -175.8(8) . . . . ?
C14 C1 C6 C7 0.9(11) . . . . ?
C5 C6 C7 C12 176.7(8) . . . . ?
C1 C6 C7 C12 -2.1(12) . . . . ?
C5 C6 C7 C8 -4.6(12) . . . . ?
C1 C6 C7 C8 176.6(7) . . . . ?
C12 C7 C8 C9 -0.9(13) . . . . ?
C6 C7 C8 C9 -179.7(8) . . . . ?
C7 C8 C9 C10 0.5(15) . . . . ?
C8 C9 C10 C11 -0.1(15) . . . . ?
C9 C10 C11 C12 0.1(14) . . . . ?
C10 C11 C12 C7 -0.6(13) . . . . ?
C10 C11 C12 C13 178.1(8) . . . . ?
C8 C7 C12 C11 0.9(12) . . . . ?
C6 C7 C12 C11 179.7(8) . . . . ?
C8 C7 C12 C13 -177.9(7) . . . . ?
C6 C7 C12 C13 0.9(11) . . . . ?
C11 C12 C13 C14 -177.1(8) . . . . ?
C7 C12 C13 C14 1.7(11) . . . . ?
C11 C12 C13 N1 1.2(13) . . . . ?
C7 C12 C13 N1 179.9(8) . . . . ?
N1 C13 C14 N2 0.8(8) . . . . ?
C12 C13 C14 N2 179.4(7) . . . . ?
N1 C13 C14 C1 178.4(7) . . . . ?
C12 C13 C14 C1 -3.0(12) . . . . ?
C2 C1 C14 C13 178.1(8) . . . . ?
C6 C1 C14 C13 1.6(11) . . . . ?
C2 C1 C14 N2 -4.9(13) . . . . ?
C6 C1 C14 N2 178.6(7) . . . . ?
N1 C16 C17 C18 104.0(12) . . . . ?
N2 C16 C17 C18 -75.3(13) . . . . ?
N1 C16 C17 C22 -76.7(11) . . . . ?
N2 C16 C17 C22 104.0(11) . . . . ?
C22 C17 C18 C19 2.8(17) . . . . ?
C16 C17 C18 C19 -177.9(10) . . . . ?
C17 C18 C19 C20 -1.5(18) . . . . ?
C18 C19 C20 C21 -1.2(17) . . . . ?
C19 C20 C21 C22 2.4(17) . . . . ?
C20 C21 C22 C17 -1.0(16) . . . . ?
C18 C17 C22 C21 -1.5(15) . . . . ?
C16 C17 C22 C21 179.2(9) . . . . ?
C28 C23 C24 C25 0.6(14) . . . . ?
N1 C23 C24 C25 -178.2(8) . . . . ?
C23 C24 C25 C26 0.3(16) . . . . ?
C24 C25 C26 C27 0(2) . . . . ?
C25 C26 C27 C28 0(2) . . . . ?
C26 C27 C28 C23 1.2(17) . . . . ?
C24 C23 C28 C27 -1.4(15) . . . . ?
N1 C23 C28 C27 177.4(9) . . . . ?
N2 C16 N1 C13 -1.0(9) . . . . ?
C17 C16 N1 C13 179.6(8) . . . . ?
N2 C16 N1 C23 178.4(7) . . . . ?
C17 C16 N1 C23 -1.1(13) . . . . ?
C14 C13 N1 C16 0.1(9) . . . . ?
C12 C13 N1 C16 -178.4(8) . . . . ?
C14 C13 N1 C23 -179.3(8) . . . . ?
C12 C13 N1 C23 2.3(13) . . . . ?
C24 C23 N1 C16 -85.0(10) . . . . ?
C28 C23 N1 C16 96.1(10) . . . . ?
C24 C23 N1 C13 94.2(10) . . . . ?
C28 C23 N1 C13 -84.6(10) . . . . ?
N1 C16 N2 C14 1.5(9) . . . . ?
C17 C16 N2 C14 -179.1(8) . . . . ?
N1 C16 N2 C15 175.7(7) . . . . ?
C17 C16 N2 C15 -4.9(13) . . . . ?
C13 C14 N2 C16 -1.4(9) . . . . ?
C1 C14 N2 C16 -178.8(7) . . . . ?
C13 C14 N2 C15 -175.2(8) . . . . ?
C1 C14 N2 C15 7.4(13) . . . . ?

_refine_diff_density_max         0.685
_refine_diff_density_min         -0.938
_refine_diff_density_rms         0.102



