# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 2064042'
loop_
_audit_author_name
_audit_author_address
'Arshad Khan'
;Hunan University
China
;
_audit_update_record             
;
2021-02-20 deposited with the CCDC.	2021-10-28 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            'C29 H15 N5'
_chemical_formula_weight         433.46

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.9500(14)
_cell_length_b                   7.9410(16)
_cell_length_c                   21.253(4)
_cell_angle_alpha                96.36(3)
_cell_angle_beta                 93.79(3)
_cell_angle_gamma                101.98(3)
_cell_volume                     1135.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      12

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9655
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4559
_diffrn_reflns_av_unetI/netI     0.0960
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.936
_diffrn_reflns_theta_max         25.365
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4185
_reflns_number_gt                1664
_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)+(0.0550P)²] 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       0.0093(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4185
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1922
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1721
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 0.7348(6) 1.5176(6) 0.9831(2) 0.0739(14) Uani 1 1 d . . . . .
H1A H 0.7325 1.6112 0.9605 0.089 Uiso 1 1 calc R U . . .
N1 N 0.6769(6) 1.5956(5) 0.82646(18) 0.0930(14) Uani 1 1 d . . . . .
C2 C 0.7842(7) 1.5487(8) 1.0485(2) 0.0909(17) Uani 1 1 d . . . . .
H2A H 0.8137 1.6613 1.0696 0.109 Uiso 1 1 calc R U . . .
C3 C 0.7884(7) 1.4124(8) 1.0808(2) 0.0975(19) Uani 1 1 d . . . . .
H3A H 0.8192 1.4328 1.1247 0.117 Uiso 1 1 calc R U . . .
C4 C 0.7496(7) 1.2483(6) 1.0519(2) 0.083 Uani 1 1 d . . . . .
H4A H 0.7557 1.1566 1.0751 0.099 Uiso 1 1 calc R U . . .
C5 C 0.6991(6) 1.2174(6) 0.9850(2) 0.082 Uani 1 1 d . . . . .
H5A H 0.6724 1.1045 0.9643 0.099 Uiso 1 1 calc R U . . .
C6 C 0.6894(6) 1.3527(5) 0.95097(18) 0.0567(11) Uani 1 1 d . . . . .
C7 C 0.6361(6) 1.3171(5) 0.88119(17) 0.0498(10) Uani 1 1 d . . . . .
C8 C 0.6603(6) 1.4720(6) 0.85017(19) 0.0626(12) Uani 1 1 d . . . . .
C9 C 0.5713(5) 1.1608(5) 0.84860(17) 0.0531(10) Uani 1 1 d . . . . .
H9A H 0.5568 1.0712 0.8738 0.064 Uiso 1 1 calc R U . . .
C10 C 0.5181(5) 1.1017(4) 0.78098(17) 0.0462(10) Uani 1 1 d . . . . .
C11 C 0.4770(5) 0.9256(5) 0.76236(18) 0.0529(11) Uani 1 1 d . . . . .
H11A H 0.4785 0.8522 0.7935 0.063 Uiso 1 1 calc R U . . .
C12 C 0.4326(5) 0.8506(5) 0.69800(19) 0.0495(10) Uani 1 1 d . . . . .
C13 C 0.3942(6) 0.6696(5) 0.6801(2) 0.0630(12) Uani 1 1 d . . . . .
H13A H 0.3965 0.5957 0.7110 0.076 Uiso 1 1 calc R U . . .
C14 C 0.3543(6) 0.6036(6) 0.6184(2) 0.0714(14) Uani 1 1 d . . . . .
H14A H 0.3299 0.4840 0.6071 0.086 Uiso 1 1 calc R U . . .
C15 C 0.3490(6) 0.7105(6) 0.5716(2) 0.0737(15) Uani 1 1 d . . . . .
H15A H 0.3192 0.6619 0.5293 0.088 Uiso 1 1 calc R U . . .
C16 C 0.3871(6) 0.8874(6) 0.58661(19) 0.0655(12) Uani 1 1 d . . . . .
H16A H 0.3849 0.9581 0.5546 0.079 Uiso 1 1 calc R U . . .
C17 C 0.4298(5) 0.9620(5) 0.65100(18) 0.0507(10) Uani 1 1 d . . . . .
C18 C 0.4667(5) 1.1420(5) 0.67002(18) 0.0564(11) Uani 1 1 d . . . . .
H18A H 0.4608 1.2167 0.6396 0.068 Uiso 1 1 calc R U . . .
C19 C 0.5110(5) 1.2082(5) 0.73223(17) 0.0517(10) Uani 1 1 d . . . . .
H19A H 0.5375 1.3280 0.7431 0.062 Uiso 1 1 calc R U . . .
N2 N -0.0309(6) -0.0237(5) 0.13943(16) 0.0886(13) Uani 1 1 d . . . . .
N3 N 0.1845(5) 0.5871(4) 0.40478(16) 0.0693(11) Uani 1 1 d . . . . .
N4 N 0.1723(5) 0.2103(4) 0.51313(15) 0.0713(11) Uani 1 1 d . . . . .
N5 N -0.0459(5) -0.3943(4) 0.24795(15) 0.0687(11) Uani 1 1 d . . . . .
C20 C 0.0344(5) 0.0569(5) 0.26072(16) 0.0436(9) Uani 1 1 d . . . . .
C21 C 0.0717(5) 0.2301(4) 0.28830(16) 0.0472(10) Uani 1 1 d . . . . .
H21A H 0.0724 0.3185 0.2630 0.057 Uiso 1 1 calc R U . . .
C22 C 0.1074(5) 0.2682(4) 0.35326(16) 0.0400(9) Uani 1 1 d . . . . .
C23 C 0.1046(5) 0.1358(4) 0.39162(16) 0.0414(9) Uani 1 1 d . . . . .
C24 C 0.0669(5) -0.0345(4) 0.36440(17) 0.0472(10) Uani 1 1 d . . . . .
H24A H 0.0654 -0.1225 0.3900 0.057 Uiso 1 1 calc R U . . .
C25 C 0.0312(5) -0.0753(4) 0.29892(17) 0.0412(9) Uani 1 1 d . . . . .
C26 C -0.0021(6) 0.0130(5) 0.19276(19) 0.0557(11) Uani 1 1 d . . . . .
C27 C 0.1492(6) 0.4467(5) 0.38179(17) 0.0477(10) Uani 1 1 d . . . . .
C28 C 0.1423(6) 0.1795(5) 0.45964(18) 0.0518(11) Uani 1 1 d . . . . .
C29 C -0.0114(6) -0.2532(5) 0.27035(17) 0.0519(10) 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 C6 1.372(5) . ?
C1 C2 1.393(6) . ?
C1 H1A 0.9300 . ?
N1 C8 1.140(5) . ?
C2 C3 1.348(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.344(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.422(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.371(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.486(5) . ?
C7 C9 1.326(4) . ?
C7 C8 1.444(5) . ?
C9 C10 1.460(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.375(4) . ?
C10 C19 1.413(4) . ?
C11 C12 1.417(5) . ?
C11 H11A 0.9300 . ?
C12 C17 1.407(5) . ?
C12 C13 1.410(4) . ?
C13 C14 1.345(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.381(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.371(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.416(5) . ?
C16 H16A 0.9300 . ?
C17 C18 1.406(5) . ?
C18 C19 1.358(5) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
N2 C26 1.132(4) . ?
N3 C27 1.137(4) . ?
N4 C28 1.132(4) . ?
N5 C29 1.138(4) . ?
C20 C25 1.394(4) . ?
C20 C21 1.399(4) . ?
C20 C26 1.441(5) . ?
C21 C22 1.375(4) . ?
C21 H21A 0.9300 . ?
C22 C23 1.397(4) . ?
C22 C27 1.442(4) . ?
C23 C24 1.376(4) . ?
C23 C28 1.442(5) . ?
C24 C25 1.387(4) . ?
C24 H24A 0.9300 . ?
C25 C29 1.437(4) . ?

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
C6 C1 C2 121.8(5) . . ?
C6 C1 H1A 119.1 . . ?
C2 C1 H1A 119.1 . . ?
C3 C2 C1 118.8(5) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C4 C3 C2 122.2(5) . . ?
C4 C3 H3A 118.9 . . ?
C2 C3 H3A 118.9 . . ?
C3 C4 C5 118.7(5) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C5 C6 C1 118.0(4) . . ?
C5 C6 C7 119.5(4) . . ?
C1 C6 C7 122.5(4) . . ?
C9 C7 C8 121.3(4) . . ?
C9 C7 C6 125.2(4) . . ?
C8 C7 C6 113.4(3) . . ?
N1 C8 C7 178.6(5) . . ?
C7 C9 C10 132.7(4) . . ?
C7 C9 H9A 113.7 . . ?
C10 C9 H9A 113.7 . . ?
C11 C10 C19 116.5(4) . . ?
C11 C10 C9 117.1(4) . . ?
C19 C10 C9 126.3(3) . . ?
C10 C11 C12 123.1(4) . . ?
C10 C11 H11A 118.4 . . ?
C12 C11 H11A 118.4 . . ?
C17 C12 C13 119.7(4) . . ?
C17 C12 C11 118.3(3) . . ?
C13 C12 C11 122.0(4) . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C13 C14 C15 121.0(4) . . ?
C13 C14 H14A 119.5 . . ?
C15 C14 H14A 119.5 . . ?
C16 C15 C14 120.9(4) . . ?
C16 C15 H15A 119.5 . . ?
C14 C15 H15A 119.5 . . ?
C15 C16 C17 119.8(4) . . ?
C15 C16 H16A 120.1 . . ?
C17 C16 H16A 120.1 . . ?
C18 C17 C12 118.7(3) . . ?
C18 C17 C16 122.9(4) . . ?
C12 C17 C16 118.4(4) . . ?
C19 C18 C17 121.0(4) . . ?
C19 C18 H18A 119.5 . . ?
C17 C18 H18A 119.5 . . ?
C18 C19 C10 122.4(4) . . ?
C18 C19 H19A 118.8 . . ?
C10 C19 H19A 118.8 . . ?
C25 C20 C21 120.2(3) . . ?
C25 C20 C26 119.3(3) . . ?
C21 C20 C26 120.5(3) . . ?
C22 C21 C20 119.2(3) . . ?
C22 C21 H21A 120.4 . . ?
C20 C21 H21A 120.4 . . ?
C21 C22 C23 120.7(3) . . ?
C21 C22 C27 119.4(3) . . ?
C23 C22 C27 119.9(3) . . ?
C24 C23 C22 120.0(4) . . ?
C24 C23 C28 120.5(3) . . ?
C22 C23 C28 119.5(3) . . ?
C23 C24 C25 120.1(4) . . ?
C23 C24 H24A 119.9 . . ?
C25 C24 H24A 119.9 . . ?
C24 C25 C20 119.8(3) . . ?
C24 C25 C29 120.3(3) . . ?
C20 C25 C29 119.9(4) . . ?
N2 C26 C20 179.1(4) . . ?
N3 C27 C22 179.0(5) . . ?
N4 C28 C23 178.6(4) . . ?
N5 C29 C25 179.6(5) . . ?

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 0.4(8) . . . . ?
C1 C2 C3 C4 1.1(9) . . . . ?
C2 C3 C4 C5 -1.1(8) . . . . ?
C3 C4 C5 C6 -0.3(7) . . . . ?
C4 C5 C6 C1 1.7(7) . . . . ?
C4 C5 C6 C7 -180.0(4) . . . . ?
C2 C1 C6 C5 -1.7(7) . . . . ?
C2 C1 C6 C7 179.9(4) . . . . ?
C5 C6 C7 C9 9.1(6) . . . . ?
C1 C6 C7 C9 -172.6(4) . . . . ?
C5 C6 C7 C8 -171.2(4) . . . . ?
C1 C6 C7 C8 7.1(6) . . . . ?
C8 C7 C9 C10 2.3(7) . . . . ?
C6 C7 C9 C10 -178.0(4) . . . . ?
C7 C9 C10 C11 172.7(4) . . . . ?
C7 C9 C10 C19 -5.1(7) . . . . ?
C19 C10 C11 C12 1.1(6) . . . . ?
C9 C10 C11 C12 -176.9(3) . . . . ?
C10 C11 C12 C17 -0.2(6) . . . . ?
C10 C11 C12 C13 178.9(4) . . . . ?
C17 C12 C13 C14 -0.3(6) . . . . ?
C11 C12 C13 C14 -179.4(4) . . . . ?
C12 C13 C14 C15 -0.3(7) . . . . ?
C13 C14 C15 C16 0.9(7) . . . . ?
C14 C15 C16 C17 -0.9(7) . . . . ?
C13 C12 C17 C18 179.4(4) . . . . ?
C11 C12 C17 C18 -1.4(5) . . . . ?
C13 C12 C17 C16 0.3(5) . . . . ?
C11 C12 C17 C16 179.4(4) . . . . ?
C15 C16 C17 C18 -178.8(4) . . . . ?
C15 C16 C17 C12 0.3(6) . . . . ?
C12 C17 C18 C19 2.2(6) . . . . ?
C16 C17 C18 C19 -178.7(4) . . . . ?
C17 C18 C19 C10 -1.4(6) . . . . ?
C11 C10 C19 C18 -0.2(6) . . . . ?
C9 C10 C19 C18 177.5(4) . . . . ?
C25 C20 C21 C22 0.8(5) . . . . ?
C26 C20 C21 C22 -179.5(4) . . . . ?
C20 C21 C22 C23 -0.7(5) . . . . ?
C20 C21 C22 C27 179.0(3) . . . . ?
C21 C22 C23 C24 0.4(6) . . . . ?
C27 C22 C23 C24 -179.3(3) . . . . ?
C21 C22 C23 C28 -179.9(3) . . . . ?
C27 C22 C23 C28 0.4(6) . . . . ?
C22 C23 C24 C25 -0.2(5) . . . . ?
C28 C23 C24 C25 -179.9(4) . . . . ?
C23 C24 C25 C20 0.3(5) . . . . ?
C23 C24 C25 C29 -179.0(3) . . . . ?
C21 C20 C25 C24 -0.6(5) . . . . ?
C26 C20 C25 C24 179.7(3) . . . . ?
C21 C20 C25 C29 178.7(3) . . . . ?
C26 C20 C25 C29 -1.0(5) . . . . ?

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.039



####################################################################### 
# 
# 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_P-1_a
_database_code_depnum_ccdc_archive 'CCDC 2064043'
loop_
_audit_author_name
_audit_author_address
'Arshad Khan'
;Hunan University
China
;
_audit_update_record             
;
2021-02-20 deposited with the CCDC.	2021-10-28 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            'C2.82 H1.64 N0.27'
_chemical_formula_weight         39.32

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.951(5)
_cell_length_b                   11.055(4)
_cell_length_c                   11.472(6)
_cell_angle_alpha                61.503(13)
_cell_angle_beta                 81.140(10)
_cell_angle_gamma                82.377(10)
_cell_volume                     1093.3(10)
_cell_formula_units_Z            22
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    205
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      19.06

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             450
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12176
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.135
_diffrn_reflns_theta_max         28.390
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5418
_reflns_number_gt                3700
_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)+(0.1000P)²+0.3000P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5418
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1865
_refine_ls_wR_factor_gt          0.1616
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
N1 N 0.46408(17) -0.00411(18) 0.80294(19) 0.0415(4) Uani 1 1 d . . . . .
C1 C 0.25941(18) 0.27089(18) 0.85009(18) 0.0291(4) Uani 1 1 d . . . . .
C2 C 0.37393(19) 0.23003(19) 0.91859(18) 0.0318(4) Uani 1 1 d . . . . .
H2A H 0.3958 0.1345 0.9724 0.038 Uiso 1 1 calc R U . . .
C3 C 0.45764(19) 0.3257(2) 0.91037(18) 0.0322(4) Uani 1 1 d . . . . .
H3A H 0.5355 0.2945 0.9584 0.039 Uiso 1 1 calc R U . . .
C4 C 0.42866(18) 0.46709(19) 0.83234(17) 0.0284(4) Uani 1 1 d . . . . .
C5 C 0.31220(16) 0.51122(18) 0.76100(17) 0.0253(4) Uani 1 1 d . . . . .
C6 C 0.22600(17) 0.41279(18) 0.77114(17) 0.0268(4) Uani 1 1 d . . . . .
C7 C 0.51227(18) 0.5701(2) 0.82045(19) 0.0323(4) Uani 1 1 d . . . . .
H7A H 0.5901 0.5420 0.8684 0.039 Uiso 1 1 calc R U . . .
C8 C 0.4822(2) 0.7055(2) 0.7427(2) 0.0360(4) Uani 1 1 d . . . . .
H8A H 0.5393 0.7708 0.7373 0.043 Uiso 1 1 calc R U . . .
C9 C 0.36689(19) 0.75319(19) 0.66835(19) 0.0321(4) Uani 1 1 d . . . . .
C10 C 0.28161(17) 0.65432(18) 0.67866(17) 0.0269(4) Uani 1 1 d . . . . .
C11 C 0.3336(2) 0.8939(2) 0.5875(2) 0.0418(5) Uani 1 1 d . . . . .
H11A H 0.3897 0.9607 0.5804 0.050 Uiso 1 1 calc R U . . .
C12 C 0.2206(2) 0.9363(2) 0.5182(2) 0.0470(5) Uani 1 1 d . . . . .
H12A H 0.1995 1.0319 0.4640 0.056 Uiso 1 1 calc R U . . .
C13 C 0.1381(2) 0.8413(2) 0.5267(2) 0.0431(5) Uani 1 1 d . . . . .
H13A H 0.0609 0.8723 0.4777 0.052 Uiso 1 1 calc R U . . .
C14 C 0.16620(18) 0.69936(19) 0.60656(19) 0.0321(4) Uani 1 1 d . . . . .
C15 C 0.08260(18) 0.5985(2) 0.6174(2) 0.0350(4) Uani 1 1 d . . . . .
H15A H 0.0052 0.6277 0.5689 0.042 Uiso 1 1 calc R U . . .
C16 C 0.11098(18) 0.4627(2) 0.6951(2) 0.0334(4) Uani 1 1 d . . . . .
H16A H 0.0533 0.3984 0.6996 0.040 Uiso 1 1 calc R U . . .
C17 C 0.16813(19) 0.17060(19) 0.86048(19) 0.0332(4) Uani 1 1 d . . . . .
H17A H 0.0730 0.1910 0.8737 0.040 Uiso 1 1 calc R U . . .
C18 C 0.20689(19) 0.05291(19) 0.85295(18) 0.0324(4) Uani 1 1 d . . . . .
C19 C 0.3504(2) 0.01978(19) 0.8281(2) 0.0344(4) Uani 1 1 d . . . . .
C20 C 0.11286(18) -0.04324(18) 0.85725(18) 0.0298(4) Uani 1 1 d . . . . .
C21 C -0.01673(19) 0.0046(2) 0.81595(19) 0.0353(4) Uani 1 1 d . . . . .
H21A H -0.0463 0.0989 0.7873 0.042 Uiso 1 1 calc R U . . .
C22 C -0.1023(2) -0.0835(2) 0.8162(2) 0.0378(4) Uani 1 1 d . . . . .
H22A H -0.1907 -0.0489 0.7885 0.045 Uiso 1 1 calc R U . . .
C23 C -0.0631(2) -0.2208(2) 0.85575(19) 0.0357(4) Uani 1 1 d . . . . .
C24 C 0.0649(2) -0.2701(2) 0.9008(2) 0.0396(5) Uani 1 1 d . . . . .
H24A H 0.0928 -0.3651 0.9319 0.047 Uiso 1 1 calc R U . . .
C25 C 0.1536(2) -0.18129(19) 0.9011(2) 0.0341(4) Uani 1 1 d . . . . .
H25A H 0.2411 -0.2159 0.9312 0.041 Uiso 1 1 calc R U . . .
C26 C -0.1546(2) -0.3159(2) 0.8503(2) 0.0472(5) Uani 1 1 d . . . . .
H26A H -0.1089 -0.4086 0.8823 0.071 Uiso 1 1 calc R U . . .
H26B H -0.2400 -0.3196 0.9069 0.071 Uiso 1 1 calc R U . . .
H26C H -0.1742 -0.2813 0.7581 0.071 Uiso 1 1 calc R U . . .
N2 N 0.80441(17) 0.33399(18) 0.72675(19) 0.0439(4) Uani 1 1 d . . . . .
N3 N 0.23653(16) 0.25512(17) 0.50815(18) 0.0385(4) Uani 1 1 d . . . . .
C27 C 0.71865(17) 0.38290(18) 0.65905(19) 0.0307(4) Uani 1 1 d . . . . .
C28 C 0.60829(16) 0.44215(17) 0.57721(16) 0.0245(3) Uani 1 1 d . . . . .
C29 C 0.51780(16) 0.35654(17) 0.57795(17) 0.0250(3) Uani 1 1 d . . . . .
H29A H 0.5302 0.2594 0.6304 0.030 Uiso 1 1 calc R U . . .
C30 C 0.40863(16) 0.41410(17) 0.50118(16) 0.0243(3) Uani 1 1 d . . . . .
C31 C 0.31316(17) 0.32548(18) 0.50444(18) 0.0281(4) 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 C19 1.151(2) . ?
C1 C2 1.386(3) . ?
C1 C6 1.411(2) . ?
C1 C17 1.475(2) . ?
C2 C3 1.392(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.397(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.418(2) . ?
C4 C7 1.441(2) . ?
C5 C10 1.422(2) . ?
C5 C6 1.425(2) . ?
C6 C16 1.434(3) . ?
C7 C8 1.347(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.427(3) . ?
C8 H8A 0.9500 . ?
C9 C11 1.404(3) . ?
C9 C10 1.421(2) . ?
C10 C14 1.414(3) . ?
C11 C12 1.377(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.376(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.404(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.425(3) . ?
C15 C16 1.348(3) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C18 1.346(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.446(3) . ?
C18 C20 1.486(2) . ?
C20 C25 1.383(3) . ?
C20 C21 1.391(3) . ?
C21 C22 1.375(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.379(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.392(3) . ?
C23 C26 1.507(3) . ?
C24 C25 1.406(3) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N2 C27 1.142(2) . ?
N3 C31 1.142(2) . ?
C27 C28 1.434(2) . ?
C28 C29 1.387(2) . ?
C28 C30 1.405(2) 2_666 ?
C29 C30 1.392(2) . ?
C29 H29A 0.9500 . ?
C30 C28 1.405(2) 2_666 ?
C30 C31 1.437(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.34(16) . . ?
C2 C1 C17 122.03(17) . . ?
C6 C1 C17 118.60(16) . . ?
C1 C2 C3 121.53(17) . . ?
C1 C2 H2A 119.2 . . ?
C3 C2 H2A 119.2 . . ?
C2 C3 C4 120.85(17) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C3 C4 C5 118.58(16) . . ?
C3 C4 C7 122.92(17) . . ?
C5 C4 C7 118.50(17) . . ?
C4 C5 C10 119.86(15) . . ?
C4 C5 C6 120.29(16) . . ?
C10 C5 C6 119.86(16) . . ?
C1 C6 C5 119.40(16) . . ?
C1 C6 C16 122.49(16) . . ?
C5 C6 C16 118.05(16) . . ?
C8 C7 C4 121.28(17) . . ?
C8 C7 H7A 119.4 . . ?
C4 C7 H7A 119.4 . . ?
C7 C8 C9 121.61(17) . . ?
C7 C8 H8A 119.2 . . ?
C9 C8 H8A 119.2 . . ?
C11 C9 C10 119.05(18) . . ?
C11 C9 C8 122.38(17) . . ?
C10 C9 C8 118.56(17) . . ?
C14 C10 C9 119.50(17) . . ?
C14 C10 C5 120.31(16) . . ?
C9 C10 C5 120.19(16) . . ?
C12 C11 C9 120.79(19) . . ?
C12 C11 H11A 119.6 . . ?
C9 C11 H11A 119.6 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C12 C13 C14 121.0(2) . . ?
C12 C13 H13A 119.5 . . ?
C14 C13 H13A 119.5 . . ?
C13 C14 C10 119.05(17) . . ?
C13 C14 C15 122.33(18) . . ?
C10 C14 C15 118.62(17) . . ?
C16 C15 C14 121.44(17) . . ?
C16 C15 H15A 119.3 . . ?
C14 C15 H15A 119.3 . . ?
C15 C16 C6 121.71(17) . . ?
C15 C16 H16A 119.1 . . ?
C6 C16 H16A 119.1 . . ?
C18 C17 C1 126.19(18) . . ?
C18 C17 H17A 116.9 . . ?
C1 C17 H17A 116.9 . . ?
C17 C18 C19 118.97(17) . . ?
C17 C18 C20 125.21(17) . . ?
C19 C18 C20 115.62(16) . . ?
N1 C19 C18 177.3(2) . . ?
C25 C20 C21 119.13(17) . . ?
C25 C20 C18 120.39(17) . . ?
C21 C20 C18 120.48(17) . . ?
C22 C21 C20 120.50(18) . . ?
C22 C21 H21A 119.8 . . ?
C20 C21 H21A 119.8 . . ?
C21 C22 C23 121.73(19) . . ?
C21 C22 H22A 119.1 . . ?
C23 C22 H22A 119.1 . . ?
C22 C23 C24 117.98(18) . . ?
C22 C23 C26 121.70(19) . . ?
C24 C23 C26 120.32(19) . . ?
C23 C24 C25 120.93(18) . . ?
C23 C24 H24A 119.5 . . ?
C25 C24 H24A 119.5 . . ?
C20 C25 C24 119.69(18) . . ?
C20 C25 H25A 120.2 . . ?
C24 C25 H25A 120.2 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N2 C27 C28 178.4(2) . . ?
C29 C28 C30 120.59(15) . 2_666 ?
C29 C28 C27 119.40(16) . . ?
C30 C28 C27 120.00(15) 2_666 . ?
C28 C29 C30 119.49(15) . . ?
C28 C29 H29A 120.3 . . ?
C30 C29 H29A 120.3 . . ?
C29 C30 C28 119.92(15) . 2_666 ?
C29 C30 C31 119.42(15) . . ?
C28 C30 C31 120.66(15) 2_666 . ?
N3 C31 C30 179.30(19) . . ?

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 -0.6(3) . . . . ?
C17 C1 C2 C3 -178.55(16) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C2 C3 C4 C7 -179.90(16) . . . . ?
C3 C4 C5 C10 -178.76(15) . . . . ?
C7 C4 C5 C10 0.9(2) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C7 C4 C5 C6 -179.32(15) . . . . ?
C2 C1 C6 C5 1.4(2) . . . . ?
C17 C1 C6 C5 179.38(15) . . . . ?
C2 C1 C6 C16 178.55(16) . . . . ?
C17 C1 C6 C16 -3.4(2) . . . . ?
C4 C5 C6 C1 -1.6(2) . . . . ?
C10 C5 C6 C1 178.20(15) . . . . ?
C4 C5 C6 C16 -178.90(15) . . . . ?
C10 C5 C6 C16 0.9(2) . . . . ?
C3 C4 C7 C8 179.03(17) . . . . ?
C5 C4 C7 C8 -0.6(3) . . . . ?
C4 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 C11 179.62(18) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C11 C9 C10 C14 0.6(3) . . . . ?
C8 C9 C10 C14 179.55(15) . . . . ?
C11 C9 C10 C5 -179.34(16) . . . . ?
C8 C9 C10 C5 -0.4(2) . . . . ?
C4 C5 C10 C14 179.66(15) . . . . ?
C6 C5 C10 C14 -0.1(2) . . . . ?
C4 C5 C10 C9 -0.4(2) . . . . ?
C6 C5 C10 C9 179.80(15) . . . . ?
C10 C9 C11 C12 -0.4(3) . . . . ?
C8 C9 C11 C12 -179.30(18) . . . . ?
C9 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C10 -0.2(3) . . . . ?
C12 C13 C14 C15 179.96(19) . . . . ?
C9 C10 C14 C13 -0.3(3) . . . . ?
C5 C10 C14 C13 179.65(16) . . . . ?
C9 C10 C14 C15 179.51(15) . . . . ?
C5 C10 C14 C15 -0.5(2) . . . . ?
C13 C14 C15 C16 -179.74(18) . . . . ?
C10 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 C6 0.3(3) . . . . ?
C1 C6 C16 C15 -178.23(17) . . . . ?
C5 C6 C16 C15 -1.0(3) . . . . ?
C2 C1 C17 C18 -46.0(3) . . . . ?
C6 C1 C17 C18 136.0(2) . . . . ?
C1 C17 C18 C19 -2.2(3) . . . . ?
C1 C17 C18 C20 -176.92(17) . . . . ?
C17 C18 C20 C25 -154.30(19) . . . . ?
C19 C18 C20 C25 30.8(2) . . . . ?
C17 C18 C20 C21 26.4(3) . . . . ?
C19 C18 C20 C21 -148.51(18) . . . . ?
C25 C20 C21 C22 -1.2(3) . . . . ?
C18 C20 C21 C22 178.10(17) . . . . ?
C20 C21 C22 C23 -0.6(3) . . . . ?
C21 C22 C23 C24 2.4(3) . . . . ?
C21 C22 C23 C26 -177.24(18) . . . . ?
C22 C23 C24 C25 -2.4(3) . . . . ?
C26 C23 C24 C25 177.25(18) . . . . ?
C21 C20 C25 C24 1.2(3) . . . . ?
C18 C20 C25 C24 -178.13(17) . . . . ?
C23 C24 C25 C20 0.6(3) . . . . ?
C30 C28 C29 C30 -0.6(3) 2_666 . . . ?
C27 C28 C29 C30 178.39(15) . . . . ?
C28 C29 C30 C28 0.6(3) . . . 2_666 ?
C28 C29 C30 C31 -178.56(15) . . . . ?

_refine_diff_density_max         0.673
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.052



####################################################################### 
# 
# 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_X_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2064044'
loop_
_audit_author_name
_audit_author_address
'Arshad Khan'
;Hunan University
China
;
_audit_update_record             
;
2021-02-20 deposited with the CCDC.	2021-10-28 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            'C29 H18 N3'
_chemical_formula_weight         408.46

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.271(3)
_cell_length_b                   10.228(2)
_cell_length_c                   14.842(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.44(3)
_cell_angle_gamma                90
_cell_volume                     2142.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9778
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_process_details   '(North, Phillips & Mathews,1968)'
_exptl_absorpt_special_details   ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4100
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.849
_diffrn_reflns_theta_max         25.379
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3934
_reflns_number_gt                2134
_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)+(0.0800P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3934
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1699
_refine_ls_wR_factor_gt          0.1352
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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 0.11944(19) 0.1597(2) 0.37178(15) 0.0497(6) Uani 1 1 d . . . . .
N1 N 0.1883(2) -0.1488(3) 0.27900(16) 0.0851(9) Uani 1 1 d . . . . .
C2 C 0.0334(2) 0.1688(2) 0.40801(17) 0.0530(7) Uani 1 1 d . . . . .
N2 N 0.2081(2) 0.4432(3) 0.7019(2) 0.1130(11) Uani 1 1 d . . . . .
C3 C -0.0566(2) 0.1802(3) 0.3525(2) 0.0669(8) Uani 1 1 d . . . . .
H3A H -0.0601 0.1832 0.2895 0.080 Uiso 1 1 calc R U . . .
N3 N -0.0505(3) 0.4870(3) 0.7542(2) 0.1148(12) Uani 1 1 d . . . . .
C4 C -0.1378(2) 0.1868(3) 0.3910(3) 0.0793(10) Uani 1 1 d . . . . .
H4A H -0.1959 0.1946 0.3538 0.095 Uiso 1 1 calc R U . . .
C5 C -0.1346(3) 0.1818(3) 0.4857(3) 0.0822(10) Uani 1 1 d . . . . .
H5A H -0.1905 0.1865 0.5109 0.099 Uiso 1 1 calc R U . . .
C6 C -0.0517(2) 0.1704(3) 0.5401(2) 0.0714(9) Uani 1 1 d . . . . .
H6A H -0.0508 0.1673 0.6028 0.086 Uiso 1 1 calc R U . . .
C7 C 0.0346(2) 0.1631(3) 0.50432(18) 0.0566(7) Uani 1 1 d . . . . .
C8 C 0.1207(2) 0.1497(3) 0.56048(18) 0.0622(8) Uani 1 1 d . . . . .
H8A H 0.1214 0.1469 0.6232 0.075 Uiso 1 1 calc R U . . .
C9 C 0.2054(2) 0.1403(2) 0.52647(16) 0.0556(7) Uani 1 1 d . . . . .
C10 C 0.2933(3) 0.1243(3) 0.58512(19) 0.0736(9) Uani 1 1 d . . . . .
H10A H 0.2937 0.1212 0.6478 0.088 Uiso 1 1 calc R U . . .
C11 C 0.3755(3) 0.1135(3) 0.5515(2) 0.0817(10) Uani 1 1 d . . . . .
H11A H 0.4319 0.1027 0.5909 0.098 Uiso 1 1 calc R U . . .
C12 C 0.3762(2) 0.1184(3) 0.4574(2) 0.0746(9) Uani 1 1 d . . . . .
H12A H 0.4334 0.1109 0.4349 0.089 Uiso 1 1 calc R U . . .
C13 C 0.2948(2) 0.1341(3) 0.39854(19) 0.0621(8) Uani 1 1 d . . . . .
H13A H 0.2972 0.1377 0.3363 0.075 Uiso 1 1 calc R U . . .
C14 C 0.20585(19) 0.1452(2) 0.43045(16) 0.0512(7) Uani 1 1 d . . . . .
C15 C 0.11625(19) 0.1688(3) 0.27233(16) 0.0561(7) Uani 1 1 d . . . . .
H15A H 0.0953 0.2483 0.2463 0.067 Uiso 1 1 calc R U . . .
C16 C 0.13929(17) 0.0787(3) 0.21482(16) 0.0491(6) Uani 1 1 d . . . . .
C17 C 0.1674(2) -0.0474(3) 0.25121(17) 0.0591(7) Uani 1 1 d . . . . .
C18 C 0.13374(17) 0.0951(3) 0.11545(15) 0.0485(6) Uani 1 1 d . . . . .
C19 C 0.1325(2) -0.0117(3) 0.05807(17) 0.0618(8) Uani 1 1 d . . . . .
H19A H 0.1398 -0.0952 0.0830 0.074 Uiso 1 1 calc R U . . .
C20 C 0.1208(2) 0.0028(3) -0.03540(18) 0.0684(8) Uani 1 1 d . . . . .
H20A H 0.1194 -0.0712 -0.0720 0.082 Uiso 1 1 calc R U . . .
C21 C 0.11101(19) 0.1240(3) -0.07559(17) 0.0599(8) Uani 1 1 d . . . . .
C22 C 0.11472(18) 0.2306(3) -0.01825(17) 0.0600(8) Uani 1 1 d . . . . .
H22A H 0.1095 0.3139 -0.0436 0.072 Uiso 1 1 calc R U . . .
C23 C 0.12599(19) 0.2183(3) 0.07568(17) 0.0561(7) Uani 1 1 d . . . . .
H23A H 0.1284 0.2925 0.1121 0.067 Uiso 1 1 calc R U . . .
C24 C 0.0948(2) 0.1401(3) -0.17728(17) 0.0865(11) Uani 1 1 d . . . . .
H24A H 0.0899 0.2314 -0.1922 0.130 Uiso 1 1 calc R U . . .
H24B H 0.1470 0.1027 -0.2024 0.130 Uiso 1 1 calc R U . . .
H24C H 0.0373 0.0964 -0.2022 0.130 Uiso 1 1 calc R U . . .
C25 C 0.0931(2) 0.4886(3) 0.48177(19) 0.0738(9) Uani 1 1 d . . . . .
H25A H 0.1552 0.4806 0.4702 0.089 Uiso 1 1 calc R U . . .
C26 C 0.0730(3) 0.4833(3) 0.57053(19) 0.0720(9) Uani 1 1 d . . . . .
C27 C -0.0198(3) 0.4942(3) 0.58888(19) 0.0694(8) Uani 1 1 d . . . . .
C28 C 0.1493(3) 0.4618(3) 0.6436(2) 0.0845(10) Uani 1 1 d . . . . .
C29 C -0.0376(3) 0.4887(3) 0.6809(2) 0.0813(10) 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 C14 1.409(3) . ?
C1 C2 1.414(3) . ?
C1 C15 1.473(3) . ?
N1 C17 1.140(3) . ?
C2 C3 1.425(4) . ?
C2 C7 1.428(4) . ?
N2 C28 1.130(4) . ?
C3 C4 1.367(4) . ?
C3 H3A 0.9300 . ?
N3 C29 1.130(4) . ?
C4 C5 1.401(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.335(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.413(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.387(4) . ?
C8 C9 1.380(4) . ?
C8 H8A 0.9300 . ?
C9 C14 1.427(3) . ?
C9 C10 1.427(4) . ?
C10 C11 1.345(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.399(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.357(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.424(4) . ?
C13 H13A 0.9300 . ?
C15 C16 1.330(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.432(4) . ?
C16 C18 1.475(3) . ?
C18 C19 1.384(3) . ?
C18 C23 1.389(3) . ?
C19 C20 1.381(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.373(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.380(4) . ?
C21 C24 1.502(4) . ?
C22 C23 1.385(3) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C27 1.380(4) 3_566 ?
C25 C26 1.390(4) . ?
C25 H25A 0.9300 . ?
C26 C27 1.394(4) . ?
C26 C28 1.437(4) . ?
C27 C25 1.380(4) 3_566 ?
C27 C29 1.427(4) . ?

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
C14 C1 C2 120.1(2) . . ?
C14 C1 C15 121.4(2) . . ?
C2 C1 C15 118.4(2) . . ?
C1 C2 C3 123.0(2) . . ?
C1 C2 C7 119.6(2) . . ?
C3 C2 C7 117.3(3) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C5 C6 C7 121.4(3) . . ?
C5 C6 H6A 119.3 . . ?
C7 C6 H6A 119.3 . . ?
C8 C7 C6 121.6(3) . . ?
C8 C7 C2 119.0(3) . . ?
C6 C7 C2 119.4(3) . . ?
C9 C8 C7 122.3(2) . . ?
C9 C8 H8A 118.9 . . ?
C7 C8 H8A 118.9 . . ?
C8 C9 C14 119.7(2) . . ?
C8 C9 C10 121.5(3) . . ?
C14 C9 C10 118.8(3) . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10A 119.4 . . ?
C9 C10 H10A 119.4 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C13 C12 C11 121.1(3) . . ?
C13 C12 H12A 119.5 . . ?
C11 C12 H12A 119.5 . . ?
C12 C13 C14 121.1(3) . . ?
C12 C13 H13A 119.5 . . ?
C14 C13 H13A 119.5 . . ?
C1 C14 C13 123.0(2) . . ?
C1 C14 C9 119.3(2) . . ?
C13 C14 C9 117.7(2) . . ?
C16 C15 C1 128.7(2) . . ?
C16 C15 H15A 115.7 . . ?
C1 C15 H15A 115.7 . . ?
C15 C16 C17 117.6(2) . . ?
C15 C16 C18 125.5(2) . . ?
C17 C16 C18 116.8(2) . . ?
N1 C17 C16 178.6(3) . . ?
C19 C18 C23 117.5(2) . . ?
C19 C18 C16 121.3(2) . . ?
C23 C18 C16 121.1(2) . . ?
C20 C19 C18 121.5(3) . . ?
C20 C19 H19A 119.3 . . ?
C18 C19 H19A 119.3 . . ?
C21 C20 C19 121.6(3) . . ?
C21 C20 H20A 119.2 . . ?
C19 C20 H20A 119.2 . . ?
C20 C21 C22 116.9(2) . . ?
C20 C21 C24 121.7(3) . . ?
C22 C21 C24 121.3(3) . . ?
C21 C22 C23 122.5(3) . . ?
C21 C22 H22A 118.8 . . ?
C23 C22 H22A 118.8 . . ?
C22 C23 C18 120.0(2) . . ?
C22 C23 H23A 120.0 . . ?
C18 C23 H23A 120.0 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C27 C25 C26 119.0(3) 3_566 . ?
C27 C25 H25A 120.5 3_566 . ?
C26 C25 H25A 120.5 . . ?
C25 C26 C27 121.1(3) . . ?
C25 C26 C28 118.8(4) . . ?
C27 C26 C28 120.0(3) . . ?
C25 C27 C26 119.9(3) 3_566 . ?
C25 C27 C29 120.7(4) 3_566 . ?
C26 C27 C29 119.4(3) . . ?
N2 C28 C26 178.6(4) . . ?
N3 C29 C27 178.4(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
C14 C1 C2 C3 -178.4(2) . . . . ?
C15 C1 C2 C3 3.1(4) . . . . ?
C14 C1 C2 C7 -0.1(4) . . . . ?
C15 C1 C2 C7 -178.7(2) . . . . ?
C1 C2 C3 C4 179.0(3) . . . . ?
C7 C2 C3 C4 0.7(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C4 C5 C6 C7 0.0(5) . . . . ?
C5 C6 C7 C8 -179.2(3) . . . . ?
C5 C6 C7 C2 0.5(4) . . . . ?
C1 C2 C7 C8 0.5(4) . . . . ?
C3 C2 C7 C8 178.9(2) . . . . ?
C1 C2 C7 C6 -179.1(2) . . . . ?
C3 C2 C7 C6 -0.8(4) . . . . ?
C6 C7 C8 C9 179.0(2) . . . . ?
C2 C7 C8 C9 -0.7(4) . . . . ?
C7 C8 C9 C14 0.4(4) . . . . ?
C7 C8 C9 C10 -178.9(3) . . . . ?
C8 C9 C10 C11 179.1(3) . . . . ?
C14 C9 C10 C11 -0.2(4) . . . . ?
C9 C10 C11 C12 0.3(5) . . . . ?
C10 C11 C12 C13 0.0(5) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
C2 C1 C14 C13 179.4(2) . . . . ?
C15 C1 C14 C13 -2.1(4) . . . . ?
C2 C1 C14 C9 -0.2(4) . . . . ?
C15 C1 C14 C9 178.3(2) . . . . ?
C12 C13 C14 C1 -179.0(2) . . . . ?
C12 C13 C14 C9 0.5(4) . . . . ?
C8 C9 C14 C1 0.1(4) . . . . ?
C10 C9 C14 C1 179.4(2) . . . . ?
C8 C9 C14 C13 -179.5(2) . . . . ?
C10 C9 C14 C13 -0.3(4) . . . . ?
C14 C1 C15 C16 65.3(4) . . . . ?
C2 C1 C15 C16 -116.2(3) . . . . ?
C1 C15 C16 C17 3.1(4) . . . . ?
C1 C15 C16 C18 179.7(2) . . . . ?
C15 C16 C18 C19 -161.2(3) . . . . ?
C17 C16 C18 C19 15.4(4) . . . . ?
C15 C16 C18 C23 16.4(4) . . . . ?
C17 C16 C18 C23 -167.0(2) . . . . ?
C23 C18 C19 C20 -2.2(4) . . . . ?
C16 C18 C19 C20 175.5(2) . . . . ?
C18 C19 C20 C21 0.9(4) . . . . ?
C19 C20 C21 C22 0.8(4) . . . . ?
C19 C20 C21 C24 -177.9(3) . . . . ?
C20 C21 C22 C23 -1.2(4) . . . . ?
C24 C21 C22 C23 177.5(3) . . . . ?
C21 C22 C23 C18 -0.2(4) . . . . ?
C19 C18 C23 C22 1.9(4) . . . . ?
C16 C18 C23 C22 -175.8(2) . . . . ?
C27 C25 C26 C27 0.5(5) 3_566 . . . ?
C27 C25 C26 C28 178.3(3) 3_566 . . . ?
C25 C26 C27 C25 -0.5(5) . . . 3_566 ?
C28 C26 C27 C25 -178.3(3) . . . 3_566 ?
C25 C26 C27 C29 -179.9(3) . . . . ?
C28 C26 C27 C29 2.3(4) . . . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.039



