# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Gandelman419b
_database_code_depnum_ccdc_archive 'CCDC 2221687'
loop_
_audit_author_name
_audit_author_address
'Natalya Fridman'
;Technion
Israel
;
_audit_update_record             
;
2022-11-23 deposited with the CCDC.	2023-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'Gandelman419b (Kuldeep)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 N3'
_chemical_formula_sum            'C24 H21 N3'
_chemical_formula_weight         351.44

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/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                   12.4541(11)
_cell_length_b                   14.0752(12)
_cell_length_c                   11.4174(10)
_cell_angle_alpha                90
_cell_angle_beta                 113.841(2)
_cell_angle_gamma                90
_cell_volume                     1830.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3244
_cell_measurement_theta_min      1.788
_cell_measurement_theta_max      25.100

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX2 (Bruker AXS)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 95
_diffrn_reflns_number            18653
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_av_R_equivalents  0.1134
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.788
_diffrn_reflns_theta_max         25.100
_diffrn_reflns_theta_full        25.100
_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             3244
_reflns_number_gt                2028
_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       'Bruker Instrument Service v2010.7.0.0'
_computing_cell_refinement       'APEX2 v2010.7-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0700P)²+0.5347P] 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         3244
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1209
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1556
_refine_ls_wR_factor_gt          0.1295
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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 0.36399(16) 0.23868(15) 0.52213(18) 0.0389(5) Uani 1 1 d . . . . .
N2 N 0.25468(16) 0.28822(15) 0.47605(18) 0.0383(5) Uani 1 1 d . . . . .
N3 N 0.15725(16) 0.22518(14) 0.43778(18) 0.0386(5) Uani 1 1 d . . . . .
C1 C 0.3661(2) 0.16736(17) 0.4332(2) 0.0358(6) Uani 1 1 d . . . . .
C2 C 0.4708(2) 0.13471(19) 0.4367(2) 0.0448(7) Uani 1 1 d . . . . .
H2 H 0.5426 0.1591 0.4982 0.054 Uiso 1 1 calc R U . . .
C3 C 0.4719(2) 0.06563(19) 0.3497(3) 0.0510(7) Uani 1 1 d . . . . .
H3 H 0.5449 0.0429 0.3532 0.061 Uiso 1 1 calc R U . . .
C4 C 0.3703(2) 0.02998(19) 0.2597(3) 0.0477(7) Uani 1 1 d . . . . .
H4 H 0.3736 -0.0151 0.1994 0.057 Uiso 1 1 calc R U . . .
C5 C 0.2599(2) 0.05940(18) 0.2552(2) 0.0402(6) Uani 1 1 d . . . . .
C6 C 0.1527(2) 0.01841(19) 0.1739(2) 0.0492(7) Uani 1 1 d . . . . .
H6 H 0.1513 -0.0275 0.1123 0.059 Uiso 1 1 calc R U . . .
C7 C 0.0507(2) 0.04399(19) 0.1828(2) 0.0484(7) Uani 1 1 d . . . . .
H7 H -0.0203 0.0135 0.1292 0.058 Uiso 1 1 calc R U . . .
C8 C 0.0475(2) 0.11393(18) 0.2687(2) 0.0414(6) Uani 1 1 d . . . . .
H8 H -0.0248 0.1307 0.2727 0.050 Uiso 1 1 calc R U . . .
C9 C 0.1499(2) 0.15804(17) 0.3471(2) 0.0356(6) Uani 1 1 d . . . . .
C10 C 0.2590(2) 0.13025(17) 0.3439(2) 0.0341(6) Uani 1 1 d . . . . .
C11 C 0.24933(19) 0.36013(17) 0.3850(2) 0.0348(6) Uani 1 1 d . . . . .
C12 C 0.3396(2) 0.42622(19) 0.4204(2) 0.0460(7) Uani 1 1 d . . . . .
H12 H 0.4056 0.4191 0.4997 0.055 Uiso 1 1 calc R U . . .
C13 C 0.3348(2) 0.5019(2) 0.3424(2) 0.0457(7) Uani 1 1 d . . . . .
H13 H 0.3978 0.5461 0.3691 0.055 Uiso 1 1 calc R U . . .
C14 C 0.2398(2) 0.51570(18) 0.2250(2) 0.0368(6) Uani 1 1 d . . . . .
C15 C 0.1511(2) 0.44867(18) 0.1909(2) 0.0378(6) Uani 1 1 d . . . . .
H15 H 0.0856 0.4551 0.1112 0.045 Uiso 1 1 calc R U . . .
C16 C 0.1548(2) 0.37245(18) 0.2693(2) 0.0383(6) Uani 1 1 d . . . . .
H16 H 0.0917 0.3283 0.2432 0.046 Uiso 1 1 calc R U . . .
C17 C 0.3932(2) 0.2039(2) 0.6522(2) 0.0500(7) Uani 1 1 d . . . . .
H17A H 0.4011 0.2579 0.7093 0.075 Uiso 1 1 calc R U . . .
H17B H 0.4674 0.1688 0.6819 0.075 Uiso 1 1 calc R U . . .
H17C H 0.3306 0.1618 0.6524 0.075 Uiso 1 1 calc R U . . .
C18 C 0.0582(2) 0.2593(2) 0.4611(2) 0.0485(7) Uani 1 1 d . . . . .
H18A H 0.0863 0.2976 0.5395 0.073 Uiso 1 1 calc R U . . .
H18B H 0.0131 0.2051 0.4710 0.073 Uiso 1 1 calc R U . . .
H18C H 0.0078 0.2983 0.3886 0.073 Uiso 1 1 calc R U . . .
C19 C 0.23419(19) 0.59842(18) 0.1430(2) 0.0372(6) Uani 1 1 d . . . . .
C20 C 0.2749(2) 0.6869(2) 0.1967(3) 0.0465(7) Uani 1 1 d . . . . .
H20 H 0.3085 0.6934 0.2873 0.056 Uiso 1 1 calc R U . . .
C21 C 0.2677(2) 0.7650(2) 0.1221(3) 0.0534(8) Uani 1 1 d . . . . .
H21 H 0.2965 0.8245 0.1616 0.064 Uiso 1 1 calc R U . . .
C22 C 0.2192(2) 0.7582(2) -0.0092(3) 0.0552(8) Uani 1 1 d . . . . .
H22 H 0.2122 0.8128 -0.0606 0.066 Uiso 1 1 calc R U . . .
C23 C 0.1809(2) 0.6706(2) -0.0650(3) 0.0534(8) Uani 1 1 d . . . . .
H23 H 0.1499 0.6645 -0.1556 0.064 Uiso 1 1 calc R U . . .
C24 C 0.1874(2) 0.5919(2) 0.0099(2) 0.0431(7) Uani 1 1 d . . . . .
H24 H 0.1595 0.5323 -0.0300 0.052 Uiso 1 1 calc R 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 N2 1.427(3) . ?
N1 C1 1.435(3) . ?
N1 C17 1.463(3) . ?
N2 N3 1.422(3) . ?
N2 C11 1.433(3) . ?
N3 C9 1.377(3) . ?
N3 C18 1.446(3) . ?
C1 C2 1.368(3) . ?
C1 C10 1.412(3) . ?
C2 C3 1.394(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.362(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.417(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.406(4) . ?
C5 C10 1.425(3) . ?
C6 C7 1.363(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.401(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.375(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.429(3) . ?
C11 C16 1.380(3) . ?
C11 C12 1.388(3) . ?
C12 C13 1.374(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(3) . ?
C14 C19 1.477(3) . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.390(3) . ?
C19 C24 1.394(3) . ?
C20 C21 1.371(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.375(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

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
N2 N1 C1 111.63(17) . . ?
N2 N1 C17 110.25(17) . . ?
C1 N1 C17 114.6(2) . . ?
N3 N2 N1 112.13(18) . . ?
N3 N2 C11 115.72(18) . . ?
N1 N2 C11 111.73(16) . . ?
C9 N3 N2 116.64(16) . . ?
C9 N3 C18 124.3(2) . . ?
N2 N3 C18 114.97(19) . . ?
C2 C1 C10 120.5(2) . . ?
C2 C1 N1 120.3(2) . . ?
C10 C1 N1 119.17(19) . . ?
C1 C2 C3 119.8(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 123.6(2) . . ?
C6 C5 C10 118.6(2) . . ?
C4 C5 C10 117.7(2) . . ?
C7 C6 C5 120.6(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 121.9(2) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C9 C8 C7 119.5(2) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 N3 124.2(2) . . ?
C8 C9 C10 120.1(2) . . ?
N3 C9 C10 115.6(2) . . ?
C1 C10 C5 119.7(2) . . ?
C1 C10 C9 120.7(2) . . ?
C5 C10 C9 119.4(2) . . ?
C16 C11 C12 118.2(2) . . ?
C16 C11 N2 123.7(2) . . ?
C12 C11 N2 117.8(2) . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 121.9(2) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 116.4(2) . . ?
C15 C14 C19 122.1(2) . . ?
C13 C14 C19 121.5(2) . . ?
C14 C15 C16 122.1(2) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
C11 C16 C15 120.5(2) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 117.2(2) . . ?
C20 C19 C14 120.8(2) . . ?
C24 C19 C14 122.0(2) . . ?
C21 C20 C19 121.6(3) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C22 120.7(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C23 118.9(3) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C22 C23 C24 120.5(3) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C19 121.0(3) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?

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
C1 N1 N2 N3 51.6(2) . . . . ?
C17 N1 N2 N3 -77.0(2) . . . . ?
C1 N1 N2 C11 -80.2(2) . . . . ?
C17 N1 N2 C11 151.3(2) . . . . ?
N1 N2 N3 C9 -56.0(2) . . . . ?
C11 N2 N3 C9 73.8(3) . . . . ?
N1 N2 N3 C18 145.65(19) . . . . ?
C11 N2 N3 C18 -84.6(2) . . . . ?
N2 N1 C1 C2 158.1(2) . . . . ?
C17 N1 C1 C2 -75.7(3) . . . . ?
N2 N1 C1 C10 -23.0(3) . . . . ?
C17 N1 C1 C10 103.2(2) . . . . ?
C10 C1 C2 C3 1.3(4) . . . . ?
N1 C1 C2 C3 -179.8(2) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C5 -2.6(4) . . . . ?
C3 C4 C5 C6 -173.1(2) . . . . ?
C3 C4 C5 C10 2.7(4) . . . . ?
C4 C5 C6 C7 173.8(2) . . . . ?
C10 C5 C6 C7 -2.0(4) . . . . ?
C5 C6 C7 C8 2.5(4) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
C7 C8 C9 N3 -177.7(2) . . . . ?
C7 C8 C9 C10 -2.2(3) . . . . ?
N2 N3 C9 C8 -157.2(2) . . . . ?
C18 N3 C9 C8 -1.1(4) . . . . ?
N2 N3 C9 C10 27.1(3) . . . . ?
C18 N3 C9 C10 -176.8(2) . . . . ?
C2 C1 C10 C5 -1.1(3) . . . . ?
N1 C1 C10 C5 -180.0(2) . . . . ?
C2 C1 C10 C9 174.5(2) . . . . ?
N1 C1 C10 C9 -4.4(3) . . . . ?
C6 C5 C10 C1 175.1(2) . . . . ?
C4 C5 C10 C1 -0.9(3) . . . . ?
C6 C5 C10 C9 -0.5(3) . . . . ?
C4 C5 C10 C9 -176.6(2) . . . . ?
C8 C9 C10 C1 -173.0(2) . . . . ?
N3 C9 C10 C1 2.8(3) . . . . ?
C8 C9 C10 C5 2.6(3) . . . . ?
N3 C9 C10 C5 178.4(2) . . . . ?
N3 N2 C11 C16 3.0(3) . . . . ?
N1 N2 C11 C16 133.0(2) . . . . ?
N3 N2 C11 C12 176.9(2) . . . . ?
N1 N2 C11 C12 -53.2(3) . . . . ?
C16 C11 C12 C13 0.0(4) . . . . ?
N2 C11 C12 C13 -174.2(2) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C12 C13 C14 C19 178.6(2) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C19 C14 C15 C16 -178.2(2) . . . . ?
C12 C11 C16 C15 0.4(3) . . . . ?
N2 C11 C16 C15 174.2(2) . . . . ?
C14 C15 C16 C11 -0.9(3) . . . . ?
C15 C14 C19 C20 141.6(2) . . . . ?
C13 C14 C19 C20 -37.4(3) . . . . ?
C15 C14 C19 C24 -37.8(3) . . . . ?
C13 C14 C19 C24 143.2(2) . . . . ?
C24 C19 C20 C21 1.0(3) . . . . ?
C14 C19 C20 C21 -178.3(2) . . . . ?
C19 C20 C21 C22 0.2(4) . . . . ?
C20 C21 C22 C23 -1.9(4) . . . . ?
C21 C22 C23 C24 2.3(4) . . . . ?
C22 C23 C24 C19 -1.0(4) . . . . ?
C20 C19 C24 C23 -0.6(3) . . . . ?
C14 C19 C24 C23 178.7(2) . . . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_Gandelman452b
_database_code_depnum_ccdc_archive 'CCDC 2221688'
loop_
_audit_author_name
_audit_author_address
'Natalya Fridman'
;Technion
Israel
;
_audit_update_record             
;
2022-11-23 deposited with the CCDC.	2023-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'Gandelman452b (Kuldeep)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C78 H90 I8 Li8 N18'
_chemical_formula_sum            'C78 H90 I8 Li8 N18'
_chemical_formula_weight         2350.39

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li -0.0003 0.0001 '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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   17.321(3)
_cell_length_b                   17.321(3)
_cell_length_c                   25.467(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     6617(3)
_cell_formula_units_Z            3
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2591
_cell_measurement_theta_min      1.576
_cell_measurement_theta_max      25.064

_exptl_crystal_description       cube
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_F_000             3396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.864
_shelx_estimated_absorpt_T_min   0.585
_shelx_estimated_absorpt_T_max   0.627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.565
_exptl_absorpt_correction_T_max  0.607
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX2 (Bruker AXS)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 95
_diffrn_reflns_number            6203
_diffrn_reflns_av_unetI/netI     0.1016
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.576
_diffrn_reflns_theta_max         25.064
_diffrn_reflns_theta_full        25.064
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2591
_reflns_number_gt                1691
_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       'Bruker Instrument Service v2010.7.0.0'
_computing_cell_refinement       'APEX2 v2010.7-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0048P)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         2591
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0685
_refine_ls_wR_factor_gt          0.0616
_refine_ls_goodness_of_fit_ref   0.875
_refine_ls_restrained_S_all      0.875
_refine_ls_shift/su_max          0.001
_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
I1 I 0.51997(3) 0.18310(3) 0.76451(2) 0.02531(13) Uani 1 1 d . . . . .
I2 I 0.6667 0.3333 0.60983(3) 0.0361(2) Uani 1 3 d S T P . .
N1 N 0.3459(3) 0.2823(3) 0.79231(19) 0.0256(13) Uani 1 1 d . . . . .
N2 N 0.3438(3) 0.2630(3) 0.73766(19) 0.0267(13) Uani 1 1 d . . . . .
N3 N 0.4203(3) 0.3409(3) 0.71728(17) 0.0258(13) Uani 1 1 d . . . . .
C1 C 0.2914(4) 0.2002(4) 0.8227(2) 0.047(2) Uani 1 1 d . . . . .
H1A H 0.2283 0.1828 0.8196 0.071 Uiso 1 1 calc R U . . .
H1B H 0.3092 0.2109 0.8597 0.071 Uiso 1 1 calc R U . . .
H1C H 0.3003 0.1524 0.8090 0.071 Uiso 1 1 calc R U . . .
C2 C 0.2603(4) 0.2444(4) 0.7113(2) 0.0424(19) Uani 1 1 d . . . . .
H2A H 0.2105 0.1896 0.7258 0.064 Uiso 1 1 calc R U . . .
H2B H 0.2652 0.2368 0.6736 0.064 Uiso 1 1 calc R U . . .
H2C H 0.2497 0.2942 0.7172 0.064 Uiso 1 1 calc R U . . .
C3 C 0.4458(5) 0.3219(5) 0.6662(2) 0.053(2) Uani 1 1 d . . . . .
H3A H 0.4446 0.2648 0.6679 0.079 Uiso 1 1 calc R U . . .
H3B H 0.5060 0.3694 0.6572 0.079 Uiso 1 1 calc R U . . .
H3C H 0.4037 0.3187 0.6394 0.079 Uiso 1 1 calc R U . . .
C4 C 0.3312(4) 0.3547(4) 0.8024(2) 0.0253(16) Uani 1 1 d . . . . .
C5 C 0.2873(4) 0.3618(5) 0.8462(2) 0.0392(18) Uani 1 1 d . . . . .
H5 H 0.2615 0.3151 0.8714 0.047 Uiso 1 1 calc R U . . .
C6 C 0.2818(5) 0.4398(6) 0.8526(3) 0.052(2) Uani 1 1 d . . . . .
H6 H 0.2515 0.4446 0.8823 0.063 Uiso 1 1 calc R U . . .
C7 C 0.3178(5) 0.5076(5) 0.8180(3) 0.054(2) Uani 1 1 d . . . . .
H7 H 0.3126 0.5591 0.8235 0.065 Uiso 1 1 calc R U . . .
C8 C 0.3624(4) 0.5021(5) 0.7746(3) 0.0333(17) Uani 1 1 d . . . . .
C9 C 0.4063(5) 0.5740(5) 0.7375(3) 0.046(2) Uani 1 1 d . . . . .
H9 H 0.4041 0.6273 0.7421 0.055 Uiso 1 1 calc R U . . .
C10 C 0.4512(5) 0.5656(5) 0.6958(3) 0.056(2) Uani 1 1 d . . . . .
H10 H 0.4812 0.6137 0.6718 0.067 Uiso 1 1 calc R U . . .
C11 C 0.4533(5) 0.4880(5) 0.6881(3) 0.0425(19) Uani 1 1 d . . . . .
H11 H 0.4829 0.4829 0.6580 0.051 Uiso 1 1 calc R U . . .
C12 C 0.4149(4) 0.4193(4) 0.7218(2) 0.0215(15) Uani 1 1 d . . . . .
C13 C 0.3682(4) 0.4245(4) 0.7656(2) 0.0195(14) Uani 1 1 d . . . . .
Li1 Li 0.4903(7) 0.3266(7) 0.7880(4) 0.035(3) Uani 1 1 d . . . . .
Li2 Li 0.6667 0.3333 0.7164(7) 0.031(5) Uani 1 3 d S T P . .


_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
I1 Li1 2.842(11) . ?
I1 Li2 2.849(8) . ?
I1 Li1 2.903(11) 2_655 ?
I1 Li1 2.938(11) 18_546 ?
I2 Li2 2.714(18) . ?
N1 C4 1.423(7) . ?
N1 N2 1.428(6) . ?
N1 C1 1.473(7) . ?
N1 Li1 2.221(12) . ?
N2 N3 1.435(6) . ?
N2 C2 1.476(7) . ?
N2 Li1 2.550(12) . ?
N3 C12 1.412(7) . ?
N3 C3 1.462(7) . ?
N3 Li1 2.254(12) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.390(8) . ?
C4 C13 1.406(8) . ?
C5 C6 1.410(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.345(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.379(9) . ?
C7 H7 0.9500 . ?
C8 C13 1.417(8) . ?
C8 C9 1.440(9) . ?
C9 C10 1.367(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.344(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.406(8) . ?
Li1 I1 2.903(11) 3_665 ?
Li1 I1 2.938(11) 17_556 ?
Li1 Li2 3.509(14) . ?
Li2 I1 2.849(8) 2_655 ?
Li2 I1 2.849(8) 3_665 ?
Li2 Li1 3.509(14) 2_655 ?
Li2 Li1 3.509(14) 3_665 ?

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
Li1 I1 Li2 76.1(2) . . ?
Li1 I1 Li1 129.3(4) . 2_655 ?
Li2 I1 Li1 75.2(2) . 2_655 ?
Li1 I1 Li1 81.8(3) . 18_546 ?
Li2 I1 Li1 123.8(4) . 18_546 ?
Li1 I1 Li1 80.7(3) 2_655 18_546 ?
C4 N1 N2 112.8(4) . . ?
C4 N1 C1 116.4(5) . . ?
N2 N1 C1 110.9(5) . . ?
C4 N1 Li1 111.8(5) . . ?
N2 N1 Li1 85.7(4) . . ?
C1 N1 Li1 115.3(5) . . ?
N1 N2 N3 103.2(4) . . ?
N1 N2 C2 113.7(5) . . ?
N3 N2 C2 112.6(5) . . ?
N1 N2 Li1 60.3(3) . . ?
N3 N2 Li1 61.6(4) . . ?
C2 N2 Li1 167.8(5) . . ?
C12 N3 N2 113.6(5) . . ?
C12 N3 C3 117.5(5) . . ?
N2 N3 C3 110.5(5) . . ?
C12 N3 Li1 109.8(4) . . ?
N2 N3 Li1 84.4(4) . . ?
C3 N3 Li1 116.5(5) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C13 119.6(6) . . ?
C5 C4 N1 124.8(6) . . ?
C13 C4 N1 115.6(5) . . ?
C4 C5 C6 118.6(7) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C7 C6 C5 122.5(7) . . ?
C7 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C6 C7 C8 119.7(7) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C13 120.2(7) . . ?
C7 C8 C9 122.6(7) . . ?
C13 C8 C9 117.2(6) . . ?
C10 C9 C8 120.0(7) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.6(7) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 122.0(7) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 119.8(6) . . ?
C11 C12 N3 123.9(6) . . ?
C13 C12 N3 116.3(5) . . ?
C12 C13 C4 120.3(6) . . ?
C12 C13 C8 120.3(6) . . ?
C4 C13 C8 119.3(6) . . ?
N1 Li1 N3 60.2(3) . . ?
N1 Li1 N2 33.9(2) . . ?
N3 Li1 N2 34.0(2) . . ?
N1 Li1 I1 111.9(4) . . ?
N3 Li1 I1 105.7(4) . . ?
N2 Li1 I1 95.3(4) . . ?
N1 Li1 I1 142.5(5) . 3_665 ?
N3 Li1 I1 95.7(4) . 3_665 ?
N2 Li1 I1 129.7(4) . 3_665 ?
I1 Li1 I1 101.7(3) . 3_665 ?
N1 Li1 I1 95.4(4) . 17_556 ?
N3 Li1 I1 151.1(5) . 17_556 ?
N2 Li1 I1 128.1(4) . 17_556 ?
I1 Li1 I1 97.6(3) . 17_556 ?
I1 Li1 I1 96.2(3) 3_665 17_556 ?
N1 Li1 Li2 148.0(5) . . ?
N3 Li1 Li2 95.0(4) . . ?
N2 Li1 Li2 114.5(4) . . ?
I1 Li1 Li2 52.02(17) . . ?
I1 Li1 Li2 51.70(17) 3_665 . ?
I1 Li1 Li2 113.0(4) 17_556 . ?
I2 Li2 I1 115.5(3) . 2_655 ?
I2 Li2 I1 115.5(3) . . ?
I1 Li2 I1 102.9(4) 2_655 . ?
I2 Li2 I1 115.5(3) . 3_665 ?
I1 Li2 I1 102.9(4) 2_655 3_665 ?
I1 Li2 I1 102.9(4) . 3_665 ?
I2 Li2 Li1 121.3(3) . 2_655 ?
I1 Li2 Li1 51.8(2) 2_655 2_655 ?
I1 Li2 Li1 53.1(2) . 2_655 ?
I1 Li2 Li1 123.2(6) 3_665 2_655 ?
I2 Li2 Li1 121.3(3) . 3_665 ?
I1 Li2 Li1 53.1(2) 2_655 3_665 ?
I1 Li2 Li1 123.2(6) . 3_665 ?
I1 Li2 Li1 51.8(2) 3_665 3_665 ?
Li1 Li2 Li1 95.4(4) 2_655 3_665 ?
I2 Li2 Li1 121.3(3) . . ?
I1 Li2 Li1 123.2(6) 2_655 . ?
I1 Li2 Li1 51.8(2) . . ?
I1 Li2 Li1 53.1(2) 3_665 . ?
Li1 Li2 Li1 95.4(4) 2_655 . ?
Li1 Li2 Li1 95.4(4) 3_665 . ?

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
C4 N1 N2 N3 66.0(5) . . . . ?
C1 N1 N2 N3 -161.4(4) . . . . ?
Li1 N1 N2 N3 -45.8(4) . . . . ?
C4 N1 N2 C2 -56.3(6) . . . . ?
C1 N1 N2 C2 76.3(6) . . . . ?
Li1 N1 N2 C2 -168.2(5) . . . . ?
C4 N1 N2 Li1 111.9(5) . . . . ?
C1 N1 N2 Li1 -115.5(5) . . . . ?
N1 N2 N3 C12 -64.1(5) . . . . ?
C2 N2 N3 C12 58.9(6) . . . . ?
Li1 N2 N3 C12 -109.2(5) . . . . ?
N1 N2 N3 C3 161.3(5) . . . . ?
C2 N2 N3 C3 -75.7(6) . . . . ?
Li1 N2 N3 C3 116.2(5) . . . . ?
N1 N2 N3 Li1 45.1(4) . . . . ?
C2 N2 N3 Li1 168.1(5) . . . . ?
N2 N1 C4 C5 146.4(6) . . . . ?
C1 N1 C4 C5 16.5(9) . . . . ?
Li1 N1 C4 C5 -118.9(6) . . . . ?
N2 N1 C4 C13 -36.4(7) . . . . ?
C1 N1 C4 C13 -166.3(5) . . . . ?
Li1 N1 C4 C13 58.3(7) . . . . ?
C13 C4 C5 C6 -0.5(9) . . . . ?
N1 C4 C5 C6 176.6(6) . . . . ?
C4 C5 C6 C7 -0.4(10) . . . . ?
C5 C6 C7 C8 -0.2(11) . . . . ?
C6 C7 C8 C13 1.6(10) . . . . ?
C6 C7 C8 C9 -176.8(6) . . . . ?
C7 C8 C9 C10 178.5(6) . . . . ?
C13 C8 C9 C10 0.1(9) . . . . ?
C8 C9 C10 C11 1.4(11) . . . . ?
C9 C10 C11 C12 -2.5(11) . . . . ?
C10 C11 C12 C13 2.1(10) . . . . ?
C10 C11 C12 N3 -175.8(6) . . . . ?
N2 N3 C12 C11 -149.7(6) . . . . ?
C3 N3 C12 C11 -18.5(9) . . . . ?
Li1 N3 C12 C11 117.8(6) . . . . ?
N2 N3 C12 C13 32.3(7) . . . . ?
C3 N3 C12 C13 163.5(5) . . . . ?
Li1 N3 C12 C13 -60.2(6) . . . . ?
C11 C12 C13 C4 -177.0(6) . . . . ?
N3 C12 C13 C4 1.0(8) . . . . ?
C11 C12 C13 C8 -0.6(8) . . . . ?
N3 C12 C13 C8 177.4(5) . . . . ?
C5 C4 C13 C12 178.4(5) . . . . ?
N1 C4 C13 C12 1.0(8) . . . . ?
C5 C4 C13 C8 1.9(8) . . . . ?
N1 C4 C13 C8 -175.5(5) . . . . ?
C7 C8 C13 C12 -178.9(6) . . . . ?
C9 C8 C13 C12 -0.4(8) . . . . ?
C7 C8 C13 C4 -2.5(9) . . . . ?
C9 C8 C13 C4 176.0(5) . . . . ?

_refine_diff_density_max         0.772
_refine_diff_density_min         -1.208
_refine_diff_density_rms         0.136

####################################################################### 
# 
# 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_Gandelman457b
_database_code_depnum_ccdc_archive 'CCDC 2221689'
loop_
_audit_author_name
_audit_author_address
'Natalya Fridman'
;Technion
Israel
;
_audit_update_record             
;
2022-11-23 deposited with the CCDC.	2023-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'Gandelman457b (Kuldeep)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H19 N3'
_chemical_formula_sum            'C15 H19 N3'
_chemical_formula_weight         241.33

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                   7.8040(16)
_cell_length_b                   8.7759(18)
_cell_length_c                   11.326(2)
_cell_angle_alpha                76.189(2)
_cell_angle_beta                 73.494(3)
_cell_angle_gamma                64.373(4)
_cell_volume                     664.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2392
_cell_measurement_theta_min      2.598
_cell_measurement_theta_max      25.232

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_F_000             260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX2 (Bruker AXS)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 95
_diffrn_reflns_number            5202
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.598
_diffrn_reflns_theta_max         25.232
_diffrn_reflns_theta_full        25.232
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2392
_reflns_number_gt                1507
_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       'Bruker Instrument Service v2010.7.0.0'
_computing_cell_refinement       'APEX2 v2010.7-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0585P)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         2392
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.966
_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 0.3609(2) 0.35420(17) 0.28191(12) 0.0318(4) Uani 1 1 d . . . . .
N2 N 0.5544(2) 0.26352(16) 0.30359(11) 0.0288(4) Uani 1 1 d . . . . .
N3 N 0.6874(2) 0.31579(17) 0.20271(11) 0.0298(4) Uani 1 1 d . . . . .
C1 C 0.2892(2) 0.5297(2) 0.26109(13) 0.0279(4) Uani 1 1 d . . . . .
C2 C 0.0940(3) 0.6334(2) 0.27866(15) 0.0366(5) Uani 1 1 d . . . . .
H2 H -0.0004 0.5846 0.3074 0.044 Uiso 1 1 calc R U . . .
C3 C 0.0355(3) 0.8111(2) 0.25386(16) 0.0424(5) Uani 1 1 d . . . . .
H3 H -0.0992 0.8814 0.2673 0.051 Uiso 1 1 calc R U . . .
C4 C 0.1669(3) 0.8859(2) 0.21090(15) 0.0392(5) Uani 1 1 d . . . . .
H4 H 0.1227 1.0067 0.1972 0.047 Uiso 1 1 calc R U . . .
C5 C 0.3683(3) 0.7845(2) 0.18676(14) 0.0313(4) Uani 1 1 d . . . . .
C6 C 0.5124(3) 0.8519(2) 0.13394(15) 0.0395(5) Uani 1 1 d . . . . .
H6 H 0.4756 0.9720 0.1188 0.047 Uiso 1 1 calc R U . . .
C7 C 0.7036(3) 0.7471(3) 0.10440(15) 0.0434(5) Uani 1 1 d . . . . .
H7 H 0.7978 0.7953 0.0678 0.052 Uiso 1 1 calc R U . . .
C8 C 0.7633(3) 0.5686(2) 0.12729(14) 0.0378(5) Uani 1 1 d . . . . .
H8 H 0.8970 0.4973 0.1060 0.045 Uiso 1 1 calc R U . . .
C9 C 0.6289(2) 0.4979(2) 0.18024(13) 0.0278(4) Uani 1 1 d . . . . .
C10 C 0.4302(2) 0.6044(2) 0.21173(13) 0.0262(4) Uani 1 1 d . . . . .
C11 C 0.2407(3) 0.2578(2) 0.30808(18) 0.0473(5) Uani 1 1 d . . . . .
H11A H 0.3233 0.1358 0.3110 0.071 Uiso 1 1 calc R U . . .
H11B H 0.1667 0.2925 0.2426 0.071 Uiso 1 1 calc R U . . .
H11C H 0.1508 0.2797 0.3884 0.071 Uiso 1 1 calc R U . . .
C12 C 0.7120(3) 0.2440(2) 0.09147(15) 0.0439(5) Uani 1 1 d . . . . .
H12A H 0.7642 0.1192 0.1090 0.066 Uiso 1 1 calc R U . . .
H12B H 0.8022 0.2795 0.0229 0.066 Uiso 1 1 calc R U . . .
H12C H 0.5860 0.2853 0.0683 0.066 Uiso 1 1 calc R U . . .
C13 C 0.5726(2) 0.2956(2) 0.42260(13) 0.0291(4) Uani 1 1 d . . . . .
H13 H 0.5579 0.4165 0.4140 0.035 Uiso 1 1 calc R U . . .
C14 C 0.7724(3) 0.1775(3) 0.44714(16) 0.0454(5) Uani 1 1 d . . . . .
H14A H 0.7864 0.0588 0.4577 0.068 Uiso 1 1 calc R U . . .
H14B H 0.7885 0.2008 0.5229 0.068 Uiso 1 1 calc R U . . .
H14C H 0.8716 0.1963 0.3767 0.068 Uiso 1 1 calc R U . . .
C15 C 0.4162(3) 0.2660(2) 0.52836(15) 0.0435(5) Uani 1 1 d . . . . .
H15A H 0.2886 0.3512 0.5151 0.065 Uiso 1 1 calc R U . . .
H15B H 0.4373 0.2760 0.6069 0.065 Uiso 1 1 calc R U . . .
H15C H 0.4213 0.1515 0.5316 0.065 Uiso 1 1 calc R 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 C1 1.378(2) . ?
N1 N2 1.4327(18) . ?
N1 C11 1.446(2) . ?
N2 N3 1.4426(18) . ?
N2 C13 1.4969(18) . ?
N3 C9 1.438(2) . ?
N3 C12 1.4693(19) . ?
C1 C2 1.379(2) . ?
C1 C10 1.432(2) . ?
C2 C3 1.403(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.366(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.414(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.414(2) . ?
C5 C10 1.419(2) . ?
C6 C7 1.364(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.407(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.369(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.413(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C15 1.512(2) . ?
C13 C14 1.515(2) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C1 N1 N2 118.27(12) . . ?
C1 N1 C11 123.40(15) . . ?
N2 N1 C11 117.11(14) . . ?
N1 N2 N3 109.52(11) . . ?
N1 N2 C13 112.05(12) . . ?
N3 N2 C13 108.54(12) . . ?
C9 N3 N2 112.27(12) . . ?
C9 N3 C12 112.54(12) . . ?
N2 N3 C12 109.42(12) . . ?
N1 C1 C2 124.04(15) . . ?
N1 C1 C10 116.26(15) . . ?
C2 C1 C10 119.61(16) . . ?
C1 C2 C3 119.74(17) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 121.86(18) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 120.31(17) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 123.65(17) . . ?
C6 C5 C10 117.69(17) . . ?
C4 C5 C10 118.60(16) . . ?
C7 C6 C5 120.96(17) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 120.97(18) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 120.00(18) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 119.88(16) . . ?
C8 C9 N3 120.65(16) . . ?
C10 C9 N3 119.47(14) . . ?
C9 C10 C5 120.47(15) . . ?
C9 C10 C1 119.59(15) . . ?
C5 C10 C1 119.79(16) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C15 110.19(13) . . ?
N2 C13 C14 108.61(13) . . ?
C15 C13 C14 110.65(14) . . ?
N2 C13 H13 109.1 . . ?
C15 C13 H13 109.1 . . ?
C14 C13 H13 109.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
C1 N1 N2 N3 -54.56(16) . . . . ?
C11 N1 N2 N3 137.64(14) . . . . ?
C1 N1 N2 C13 65.95(17) . . . . ?
C11 N1 N2 C13 -101.86(16) . . . . ?
N1 N2 N3 C9 52.95(15) . . . . ?
C13 N2 N3 C9 -69.67(15) . . . . ?
N1 N2 N3 C12 -72.75(15) . . . . ?
C13 N2 N3 C12 164.62(13) . . . . ?
N2 N1 C1 C2 -158.13(14) . . . . ?
C11 N1 C1 C2 8.9(2) . . . . ?
N2 N1 C1 C10 25.41(19) . . . . ?
C11 N1 C1 C10 -167.60(14) . . . . ?
N1 C1 C2 C3 -179.48(14) . . . . ?
C10 C1 C2 C3 -3.1(2) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C2 C3 C4 C5 1.7(2) . . . . ?
C3 C4 C5 C6 175.31(14) . . . . ?
C3 C4 C5 C10 -1.9(2) . . . . ?
C4 C5 C6 C7 -175.15(15) . . . . ?
C10 C5 C6 C7 2.1(2) . . . . ?
C5 C6 C7 C8 -0.9(2) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C7 C8 C9 N3 179.18(13) . . . . ?
N2 N3 C9 C8 153.90(13) . . . . ?
C12 N3 C9 C8 -82.12(18) . . . . ?
N2 N3 C9 C10 -26.96(18) . . . . ?
C12 N3 C9 C10 97.02(17) . . . . ?
C8 C9 C10 C5 1.2(2) . . . . ?
N3 C9 C10 C5 -177.97(12) . . . . ?
C8 C9 C10 C1 176.76(13) . . . . ?
N3 C9 C10 C1 -2.4(2) . . . . ?
C6 C5 C10 C9 -2.2(2) . . . . ?
C4 C5 C10 C9 175.18(14) . . . . ?
C6 C5 C10 C1 -177.78(13) . . . . ?
C4 C5 C10 C1 -0.4(2) . . . . ?
N1 C1 C10 C9 3.9(2) . . . . ?
C2 C1 C10 C9 -172.70(13) . . . . ?
N1 C1 C10 C5 179.54(12) . . . . ?
C2 C1 C10 C5 2.9(2) . . . . ?
N1 N2 C13 C15 50.98(17) . . . . ?
N3 N2 C13 C15 172.05(13) . . . . ?
N1 N2 C13 C14 172.34(13) . . . . ?
N3 N2 C13 C14 -66.59(16) . . . . ?

_refine_diff_density_max         0.135
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_Gandelman417b
_database_code_depnum_ccdc_archive 'CCDC 2221690'
loop_
_audit_author_name
_audit_author_address
'Natalya Fridman'
;Technion
Israel
;
_audit_update_record             
;
2022-11-23 deposited with the CCDC.	2023-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'Gandelman417b (Kuldeep)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 N3'
_chemical_formula_sum            'C18 H17 N3'
_chemical_formula_weight         275.34

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   9.832(3)
_cell_length_b                   11.907(4)
_cell_length_c                   12.610(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1476.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2601
_cell_measurement_theta_min      2.352
_cell_measurement_theta_max      25.073

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX2 (Bruker AXS)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 95
_diffrn_reflns_number            9170
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_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         2.352
_diffrn_reflns_theta_max         25.073
_diffrn_reflns_theta_full        25.073
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2601
_reflns_number_gt                1637
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.989

_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       'Bruker Instrument Service v2010.7.0.0'
_computing_cell_refinement       'APEX2 v2010.7-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0591P)²+0.4264P] 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_abs_structure_details 
;
 Flack x determined using 484 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2601
_refine_ls_number_parameters     192
_refine_ls_number_restraints     203
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1544
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.055
_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 0.4999(4) 0.5061(4) 0.8215(3) 0.0467(11) Uani 1 1 d . U . . .
N2 N 0.3633(4) 0.4793(3) 0.7962(3) 0.0462(11) Uani 1 1 d . U . . .
N3 N 0.3312(4) 0.4979(4) 0.6891(3) 0.0563(12) Uani 1 1 d . U . . .
C1 C 0.5942(5) 0.4533(4) 0.7543(4) 0.0418(12) Uani 1 1 d . U . . .
C2 C 0.7252(6) 0.4327(6) 0.7864(5) 0.0690(18) Uani 1 1 d . U . . .
H2 H 0.7547 0.4533 0.8555 0.083 Uiso 1 1 calc R U . . .
C3 C 0.8160(7) 0.3798(7) 0.7140(8) 0.095(3) Uani 1 1 d . U . . .
H3 H 0.9066 0.3640 0.7355 0.115 Uiso 1 1 calc R U . . .
C4 C 0.7757(9) 0.3521(6) 0.6164(8) 0.092(2) Uani 1 1 d . U . . .
H4 H 0.8383 0.3160 0.5703 0.110 Uiso 1 1 calc R U . . .
C5 C 0.6445(8) 0.3747(5) 0.5801(5) 0.0663(17) Uani 1 1 d . U . . .
C6 C 0.6005(11) 0.3577(7) 0.4733(6) 0.102(3) Uani 1 1 d . U . . .
H6 H 0.6580 0.3205 0.4240 0.122 Uiso 1 1 calc R U . . .
C7 C 0.4773(11) 0.3945(9) 0.4431(6) 0.120(4) Uani 1 1 d . U . . .
H7 H 0.4525 0.3883 0.3705 0.144 Uiso 1 1 calc R U . . .
C8 C 0.3868(8) 0.4403(7) 0.5119(5) 0.092(2) Uani 1 1 d . U . . .
H8 H 0.2996 0.4630 0.4876 0.110 Uiso 1 1 calc R U . . .
C9 C 0.4208(6) 0.4538(5) 0.6156(4) 0.0508(14) Uani 1 1 d . U . . .
C10 C 0.5524(6) 0.4235(4) 0.6518(4) 0.0414(12) Uani 1 1 d . U . . .
C11 C 0.3257(5) 0.3691(4) 0.8318(3) 0.0385(12) Uani 1 1 d . U . . .
C12 C 0.3978(6) 0.3138(4) 0.9104(4) 0.0463(14) Uani 1 1 d . U . . .
H12 H 0.4792 0.3455 0.9379 0.056 Uiso 1 1 calc R U . . .
C13 C 0.3506(7) 0.2127(5) 0.9483(4) 0.0538(15) Uani 1 1 d . U . . .
H13 H 0.4008 0.1751 1.0020 0.065 Uiso 1 1 calc R U . . .
C14 C 0.2335(7) 0.1645(5) 0.9109(4) 0.0564(16) Uani 1 1 d . U . . .
H14 H 0.2021 0.0951 0.9389 0.068 Uiso 1 1 calc R U . . .
C15 C 0.1628(6) 0.2182(5) 0.8327(4) 0.0599(16) Uani 1 1 d . U . . .
H15 H 0.0824 0.1852 0.8050 0.072 Uiso 1 1 calc R U . . .
C16 C 0.2073(6) 0.3201(4) 0.7933(4) 0.0521(14) Uani 1 1 d . U . . .
H16 H 0.1565 0.3570 0.7396 0.063 Uiso 1 1 calc R U . . .
C17 C 0.5196(8) 0.6222(6) 0.8425(7) 0.109(3) Uani 1 1 d . U . . .
H17A H 0.4782 0.6667 0.7857 0.163 Uiso 1 1 calc R U . . .
H17B H 0.6172 0.6384 0.8461 0.163 Uiso 1 1 calc R U . . .
H17C H 0.4768 0.6415 0.9103 0.163 Uiso 1 1 calc R U . . .
C18 C 0.2447(10) 0.5938(7) 0.6689(7) 0.141(4) Uani 1 1 d . U . . .
H18A H 0.1494 0.5697 0.6682 0.211 Uiso 1 1 calc R U . . .
H18B H 0.2681 0.6267 0.6000 0.211 Uiso 1 1 calc R U . . .
H18C H 0.2579 0.6499 0.7248 0.211 Uiso 1 1 calc R 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 C1 1.404(6) . ?
N1 N2 1.416(5) . ?
N1 C17 1.421(8) . ?
N2 N3 1.405(6) . ?
N2 C11 1.435(6) . ?
N3 C9 1.383(7) . ?
N3 C18 1.446(8) . ?
C1 C2 1.372(7) . ?
C1 C10 1.402(7) . ?
C2 C3 1.423(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.334(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(11) . ?
C4 H4 0.9500 . ?
C5 C10 1.406(7) . ?
C5 C6 1.428(11) . ?
C6 C7 1.344(12) . ?
C6 H6 0.9500 . ?
C7 C8 1.357(12) . ?
C7 H7 0.9500 . ?
C8 C9 1.359(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.419(7) . ?
C11 C12 1.385(7) . ?
C11 C16 1.390(7) . ?
C12 C13 1.376(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.370(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.366(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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
C1 N1 N2 113.0(4) . . ?
C1 N1 C17 117.3(5) . . ?
N2 N1 C17 113.0(5) . . ?
N3 N2 N1 113.2(4) . . ?
N3 N2 C11 112.8(4) . . ?
N1 N2 C11 112.3(4) . . ?
C9 N3 N2 116.2(4) . . ?
C9 N3 C18 123.8(5) . . ?
N2 N3 C18 115.2(5) . . ?
C2 C1 C10 120.1(5) . . ?
C2 C1 N1 121.5(5) . . ?
C10 C1 N1 118.4(5) . . ?
C1 C2 C3 118.6(6) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 121.0(7) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 122.0(7) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C10 117.6(7) . . ?
C4 C5 C6 124.2(7) . . ?
C10 C5 C6 118.1(7) . . ?
C7 C6 C5 119.6(7) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 122.7(8) . . ?
C6 C7 H7 118.6 . . ?
C8 C7 H7 118.6 . . ?
C7 C8 C9 120.1(8) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 N3 122.3(6) . . ?
C8 C9 C10 120.3(6) . . ?
N3 C9 C10 117.5(4) . . ?
C1 C10 C5 120.6(6) . . ?
C1 C10 C9 120.0(5) . . ?
C5 C10 C9 119.0(5) . . ?
C12 C11 C16 118.7(5) . . ?
C12 C11 N2 121.8(5) . . ?
C16 C11 N2 119.4(4) . . ?
C13 C12 C11 119.4(5) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 122.1(6) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C15 C14 C13 118.7(5) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C16 120.6(6) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 120.5(5) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C1 N1 N2 N3 -52.6(5) . . . . ?
C17 N1 N2 N3 83.4(6) . . . . ?
C1 N1 N2 C11 76.5(5) . . . . ?
C17 N1 N2 C11 -147.4(5) . . . . ?
N1 N2 N3 C9 49.0(6) . . . . ?
C11 N2 N3 C9 -79.9(5) . . . . ?
N1 N2 N3 C18 -107.7(6) . . . . ?
C11 N2 N3 C18 123.5(6) . . . . ?
N2 N1 C1 C2 -155.1(5) . . . . ?
C17 N1 C1 C2 70.9(7) . . . . ?
N2 N1 C1 C10 26.1(6) . . . . ?
C17 N1 C1 C10 -107.9(6) . . . . ?
C10 C1 C2 C3 -0.7(8) . . . . ?
N1 C1 C2 C3 -179.4(5) . . . . ?
C1 C2 C3 C4 1.0(10) . . . . ?
C2 C3 C4 C5 0.9(11) . . . . ?
C3 C4 C5 C10 -2.9(10) . . . . ?
C3 C4 C5 C6 173.2(7) . . . . ?
C4 C5 C6 C7 -172.0(7) . . . . ?
C10 C5 C6 C7 4.1(11) . . . . ?
C5 C6 C7 C8 -5.2(14) . . . . ?
C6 C7 C8 C9 2.1(13) . . . . ?
C7 C8 C9 N3 -178.7(6) . . . . ?
C7 C8 C9 C10 2.1(10) . . . . ?
N2 N3 C9 C8 163.1(5) . . . . ?
C18 N3 C9 C8 -42.5(9) . . . . ?
N2 N3 C9 C10 -17.7(7) . . . . ?
C18 N3 C9 C10 136.8(6) . . . . ?
C2 C1 C10 C5 -1.4(7) . . . . ?
N1 C1 C10 C5 177.4(4) . . . . ?
C2 C1 C10 C9 -174.4(5) . . . . ?
N1 C1 C10 C9 4.4(7) . . . . ?
C4 C5 C10 C1 3.1(7) . . . . ?
C6 C5 C10 C1 -173.2(6) . . . . ?
C4 C5 C10 C9 176.2(5) . . . . ?
C6 C5 C10 C9 -0.1(7) . . . . ?
C8 C9 C10 C1 170.1(5) . . . . ?
N3 C9 C10 C1 -9.1(7) . . . . ?
C8 C9 C10 C5 -3.0(7) . . . . ?
N3 C9 C10 C5 177.8(5) . . . . ?
N3 N2 C11 C12 149.3(4) . . . . ?
N1 N2 C11 C12 20.0(6) . . . . ?
N3 N2 C11 C16 -36.3(6) . . . . ?
N1 N2 C11 C16 -165.6(4) . . . . ?
C16 C11 C12 C13 -0.2(7) . . . . ?
N2 C11 C12 C13 174.3(4) . . . . ?
C11 C12 C13 C14 -0.2(8) . . . . ?
C12 C13 C14 C15 0.9(8) . . . . ?
C13 C14 C15 C16 -1.2(8) . . . . ?
C14 C15 C16 C11 0.8(8) . . . . ?
C12 C11 C16 C15 -0.1(7) . . . . ?
N2 C11 C16 C15 -174.7(5) . . . . ?

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.043

