# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_kdm1454
_database_code_depnum_ccdc_archive 'CCDC 2108276'
loop_
_audit_author_name
_audit_author_address
'B. Kariuki'
;Cardiff university
United Kingdom
;
_audit_update_record             
;
2021-09-07 deposited with the CCDC.	2022-10-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H32 N2'
_chemical_formula_weight         420.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   39.0954(15)
_cell_length_b                   12.9175(6)
_cell_length_c                   20.0670(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.649(3)
_cell_angle_gamma                90
_cell_volume                     10113.6(7)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4895
_cell_measurement_theta_min      3.5890
_cell_measurement_theta_max      73.9170

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_F_000             3616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.161
_exptl_absorpt_coefficient_mu    0.485
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_correction_T_min  0.88399
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20091
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.604
_diffrn_reflns_theta_max         74.082
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             9990
_reflns_number_gt                6571
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1121P)²+1.6575P] 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
_refine_ls_extinction_coef       0.00017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9990
_refine_ls_number_parameters     578
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_ref         0.2334
_refine_ls_wR_factor_gt          0.1993
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
C1A' C 0.62876(4) 0.56824(14) 0.00550(9) 0.0665(4) Uani 1 1 d . . . . .
H16A H 0.6299 0.5272 -0.0348 0.080 Uiso 1 1 calc R U . . .
H16B H 0.6513 0.5684 0.0285 0.080 Uiso 1 1 calc R U . . .
C1A C 0.61884(5) 0.67796(15) -0.01338(9) 0.0688(4) Uani 1 1 d . . . . .
H15A H 0.5964 0.6778 -0.0371 0.083 Uiso 1 1 calc R U . . .
H15B H 0.6173 0.7189 0.0269 0.083 Uiso 1 1 calc R U . . .
C3A C 0.67396(5) 0.76277(17) -0.01595(9) 0.0753(5) Uani 1 1 d . . . . .
H1A H 0.6810 0.7104 0.0167 0.090 Uiso 1 1 calc R U . . .
H1B H 0.6678 0.8244 0.0082 0.090 Uiso 1 1 calc R U . . .
C3A' C 0.62022(4) 0.43638(13) 0.08742(9) 0.0655(4) Uani 1 1 d . . . . .
H17A H 0.6322 0.3918 0.0578 0.079 Uiso 1 1 calc R U . . .
H17B H 0.6023 0.3956 0.1061 0.079 Uiso 1 1 calc R U . . .
C4A' C 0.64481(5) 0.47086(18) 0.14291(9) 0.0734(5) Uani 1 1 d . . . . .
C4A C 0.70367(4) 0.78765(15) -0.05695(9) 0.0675(4) Uani 1 1 d . . . . .
C5A C 0.71177(5) 0.72581(18) -0.10955(12) 0.0861(6) Uani 1 1 d . . . . .
H3 H 0.6980 0.6692 -0.1215 0.103 Uiso 1 1 calc R U . . .
C5A' C 0.67262(7) 0.4086(3) 0.16107(17) 0.1222(11) Uani 1 1 d . . . . .
H19 H 0.6769 0.3485 0.1376 0.147 Uiso 1 1 calc R U . . .
C6A C 0.74008(6) 0.7470(2) -0.14472(14) 0.1064(8) Uani 1 1 d . . . . .
H4 H 0.7456 0.7040 -0.1796 0.128 Uiso 1 1 calc R U . . .
C6A' C 0.69422(11) 0.4394(5) 0.2164(3) 0.202(3) Uani 1 1 d . . . . .
H20 H 0.7132 0.3989 0.2289 0.242 Uiso 1 1 calc R U . . .
C7A C 0.76023(6) 0.8314(3) -0.12844(15) 0.1053(8) Uani 1 1 d . . . . .
H5 H 0.7793 0.8456 -0.1522 0.126 Uiso 1 1 calc R U . . .
C7A' C 0.68836(14) 0.5245(6) 0.25155(16) 0.208(4) Uani 1 1 d . . . . .
H21 H 0.7024 0.5412 0.2891 0.250 Uiso 1 1 calc R U . . .
C8A C 0.75227(6) 0.8934(2) -0.07808(16) 0.1027(8) Uani 1 1 d . . . . .
H6 H 0.7657 0.9513 -0.0675 0.123 Uiso 1 1 calc R U . . .
C8A' C 0.66160(10) 0.5864(5) 0.23176(16) 0.178(2) Uani 1 1 d . . . . .
H22 H 0.6579 0.6473 0.2549 0.214 Uiso 1 1 calc R U . . .
C9A C 0.72421(5) 0.87203(17) -0.04169(12) 0.0843(6) Uani 1 1 d . . . . .
H7 H 0.7192 0.9151 -0.0065 0.101 Uiso 1 1 calc R U . . .
C9A' C 0.63978(7) 0.5600(3) 0.17764(12) 0.1107(9) Uani 1 1 d . . . . .
H23 H 0.6215 0.6032 0.1647 0.133 Uiso 1 1 calc R U . . .
C10A C 0.62816(5) 0.81021(14) -0.09518(9) 0.0668(4) Uani 1 1 d . . . . .
H8A H 0.6462 0.8495 -0.1146 0.080 Uiso 1 1 calc R U . . .
H8B H 0.6166 0.8562 -0.0657 0.080 Uiso 1 1 calc R U . . .
C11A C 0.60288(4) 0.77534(15) -0.15034(8) 0.0649(4) Uani 1 1 d . . . . .
C12A C 0.60740(5) 0.68496(18) -0.18519(10) 0.0797(5) Uani 1 1 d . . . . .
H10 H 0.6258 0.6418 -0.1731 0.096 Uiso 1 1 calc R U . . .
C13A C 0.58451(7) 0.6580(2) -0.23841(11) 0.1022(8) Uani 1 1 d . . . . .
H11 H 0.5876 0.5967 -0.2616 0.123 Uiso 1 1 calc R U . . .
C14A C 0.55757(8) 0.7209(3) -0.25672(13) 0.1139(11) Uani 1 1 d . . . . .
H12 H 0.5425 0.7029 -0.2926 0.137 Uiso 1 1 calc R U . . .
C15A C 0.55269(7) 0.8093(3) -0.22274(15) 0.1123(10) Uani 1 1 d . . . . .
H13 H 0.5342 0.8518 -0.2353 0.135 Uiso 1 1 calc R U . . .
C16A C 0.57512(5) 0.8377(2) -0.16893(12) 0.0859(6) Uani 1 1 d . . . . .
H14 H 0.5714 0.8984 -0.1456 0.103 Uiso 1 1 calc R U . . .
C24 C 0.57364(5) 0.48354(18) 0.01044(9) 0.0750(5) Uani 1 1 d . . . . .
H24A H 0.5794 0.4216 -0.0138 0.090 Uiso 1 1 calc R U . . .
H24B H 0.5662 0.5357 -0.0221 0.090 Uiso 1 1 calc R U . . .
C25 C 0.54457(4) 0.45950(15) 0.05332(9) 0.0662(4) Uani 1 1 d . . . . .
C26 C 0.52412(5) 0.37438(18) 0.03975(11) 0.0827(6) Uani 1 1 d . . . . .
H26 H 0.5289 0.3306 0.0047 0.099 Uiso 1 1 calc R U . . .
C27 C 0.49656(6) 0.3531(2) 0.07749(15) 0.1003(8) Uani 1 1 d . . . . .
H27 H 0.4831 0.2948 0.0681 0.120 Uiso 1 1 calc R U . . .
C28 C 0.48913(6) 0.4168(3) 0.12797(15) 0.1049(9) Uani 1 1 d . . . . .
H28 H 0.4703 0.4034 0.1526 0.126 Uiso 1 1 calc R U . . .
C29 C 0.50934(6) 0.5010(2) 0.14278(13) 0.1029(8) Uani 1 1 d . . . . .
H29 H 0.5043 0.5440 0.1780 0.123 Uiso 1 1 calc R U . . .
C30 C 0.53715(5) 0.52279(18) 0.10600(11) 0.0831(5) Uani 1 1 d . . . . .
H30 H 0.5509 0.5800 0.1167 0.100 Uiso 1 1 calc R U . . .
C31 C 0.93655(6) 0.41115(19) -0.04879(12) 0.0914(6) Uani 1 1 d . . . . .
H31A H 0.9447 0.3482 -0.0688 0.110 Uiso 1 1 calc R U . . .
H31B H 0.9387 0.4027 -0.0007 0.110 Uiso 1 1 calc R U . . .
C32 C 0.95852(5) 0.50067(19) -0.06823(10) 0.0807(5) Uani 1 1 d . . . . .
C33 C 0.98746(6) 0.4840(3) -0.10237(14) 0.1054(8) Uani 1 1 d . . . . .
H33 H 0.9935 0.4171 -0.1140 0.127 Uiso 1 1 calc R U . . .
C34 C 1.00760(7) 0.5675(4) -0.11943(17) 0.1259(12) Uani 1 1 d . . . . .
H34 H 1.0271 0.5560 -0.1427 0.151 Uiso 1 1 calc R U . . .
C35 C 0.99921(9) 0.6649(3) -0.10261(16) 0.1247(12) Uani 1 1 d . . . . .
H35 H 1.0129 0.7203 -0.1138 0.150 Uiso 1 1 calc R U . . .
C36 C 0.97044(9) 0.6816(2) -0.06893(15) 0.1168(10) Uani 1 1 d . . . . .
H36 H 0.9644 0.7486 -0.0575 0.140 Uiso 1 1 calc R U . . .
C37 C 0.95042(7) 0.6001(2) -0.05199(12) 0.0952(7) Uani 1 1 d . . . . .
H37 H 0.9309 0.6126 -0.0290 0.114 Uiso 1 1 calc R U . . .
C38 C 0.89533(6) 0.41297(18) -0.14266(9) 0.0819(5) Uani 1 1 d . . . . .
H38A H 0.8963 0.3397 -0.1529 0.098 Uiso 1 1 calc R U . . .
H38B H 0.9139 0.4467 -0.1639 0.098 Uiso 1 1 calc R U . . .
C39 C 0.86201(5) 0.45587(17) -0.17129(9) 0.0731(5) Uani 1 1 d . . . . .
C40 C 0.84262(7) 0.4036(2) -0.22075(11) 0.0980(8) Uani 1 1 d . . . . .
H40 H 0.8494 0.3383 -0.2343 0.118 Uiso 1 1 calc R U . . .
C41 C 0.81297(8) 0.4485(4) -0.25037(13) 0.1252(13) Uani 1 1 d . . . . .
H41 H 0.8002 0.4135 -0.2840 0.150 Uiso 1 1 calc R U . . .
C42 C 0.80273(7) 0.5430(4) -0.23013(16) 0.1265(13) Uani 1 1 d . . . . .
H42 H 0.7830 0.5732 -0.2500 0.152 Uiso 1 1 calc R U . . .
C43 C 0.82135(7) 0.5937(3) -0.18080(15) 0.1139(9) Uani 1 1 d . . . . .
H43 H 0.8140 0.6580 -0.1664 0.137 Uiso 1 1 calc R U . . .
C44 C 0.85082(6) 0.5510(2) -0.15205(11) 0.0886(6) Uani 1 1 d . . . . .
H44 H 0.8634 0.5874 -0.1189 0.106 Uiso 1 1 calc R U . . .
C45 C 0.87805(6) 0.35646(16) -0.03563(10) 0.0826(6) Uani 1 1 d . . . . .
H45A H 0.8890 0.2893 -0.0307 0.099 Uiso 1 1 calc R U . . .
H45B H 0.8567 0.3474 -0.0625 0.099 Uiso 1 1 calc R U . . .
C46 C 0.87030(6) 0.39690(15) 0.03241(10) 0.0794(5) Uani 1 1 d . . . . .
H46A H 0.8916 0.4067 0.0591 0.095 Uiso 1 1 calc R U . . .
H46B H 0.8591 0.4638 0.0274 0.095 Uiso 1 1 calc R U . . .
C47 C 0.85277(5) 0.34231(17) 0.13944(9) 0.0779(5) Uani 1 1 d . . . . .
H47A H 0.8341 0.3086 0.1606 0.093 Uiso 1 1 calc R U . . .
H47B H 0.8515 0.4158 0.1489 0.093 Uiso 1 1 calc R U . . .
C48 C 0.88608(5) 0.30098(17) 0.16937(9) 0.0724(5) Uani 1 1 d . . . . .
C49 C 0.89772(6) 0.2051(2) 0.15189(13) 0.0944(7) Uani 1 1 d . . . . .
H49 H 0.8857 0.1673 0.1186 0.113 Uiso 1 1 calc R U . . .
C50 C 0.92711(8) 0.1644(3) 0.18351(19) 0.1320(12) Uani 1 1 d . . . . .
H50 H 0.9350 0.0996 0.1714 0.158 Uiso 1 1 calc R U . . .
C51 C 0.94474(9) 0.2209(5) 0.23342(19) 0.1482(17) Uani 1 1 d . . . . .
H51 H 0.9640 0.1929 0.2563 0.178 Uiso 1 1 calc R U . . .
C52 C 0.93379(9) 0.3174(4) 0.24887(16) 0.1487(16) Uani 1 1 d . . . . .
H52 H 0.9462 0.3561 0.2811 0.178 Uiso 1 1 calc R U . . .
C53 C 0.90449(7) 0.3586(3) 0.21739(11) 0.1035(8) Uani 1 1 d . . . . .
H53 H 0.8972 0.4246 0.2284 0.124 Uiso 1 1 calc R U . . .
C54 C 0.81203(6) 0.33898(19) 0.04510(12) 0.0893(6) Uani 1 1 d . . . . .
H54A H 0.8100 0.3456 -0.0031 0.107 Uiso 1 1 calc R U . . .
H54B H 0.8033 0.4022 0.0639 0.107 Uiso 1 1 calc R U . . .
C55 C 0.79061(5) 0.24907(18) 0.06551(10) 0.0786(5) Uani 1 1 d . . . . .
C56 C 0.76179(6) 0.2645(3) 0.10029(13) 0.1043(8) Uani 1 1 d . . . . .
H56 H 0.7555 0.3313 0.1117 0.125 Uiso 1 1 calc R U . . .
C57 C 0.74213(7) 0.1807(4) 0.11840(17) 0.1259(12) Uani 1 1 d . . . . .
H57 H 0.7229 0.1918 0.1424 0.151 Uiso 1 1 calc R U . . .
C58 C 0.75066(9) 0.0831(3) 0.10149(16) 0.1265(12) Uani 1 1 d . . . . .
H58 H 0.7371 0.0275 0.1130 0.152 Uiso 1 1 calc R U . . .
C59 C 0.77929(9) 0.0668(2) 0.06744(14) 0.1177(10) Uani 1 1 d . . . . .
H59 H 0.7855 -0.0001 0.0562 0.141 Uiso 1 1 calc R U . . .
C60 C 0.79899(7) 0.1496(2) 0.04974(12) 0.0948(7) Uani 1 1 d . . . . .
H60 H 0.8185 0.1376 0.0265 0.114 Uiso 1 1 calc R U . . .
N2A N 0.64371(4) 0.72553(11) -0.05558(7) 0.0628(4) Uani 1 1 d . . . . .
N2A' N 0.60439(3) 0.52075(11) 0.04845(7) 0.0615(3) Uani 1 1 d . . . . .
N3 N 0.90044(4) 0.42664(13) -0.07026(8) 0.0741(4) Uani 1 1 d . . . . .
N4 N 0.84828(4) 0.32665(13) 0.06735(7) 0.0716(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
C1A' N2A' 1.460(2) . ?
C1A' C1A 1.511(3) . ?
C1A N2A 1.465(2) . ?
C3A N2A 1.464(2) . ?
C3A C4A 1.500(3) . ?
C3A' N2A' 1.456(2) . ?
C3A' C4A' 1.492(3) . ?
C4A' C9A' 1.367(4) . ?
C4A' C5A' 1.383(3) . ?
C4A C9A 1.377(3) . ?
C4A C5A 1.377(3) . ?
C5A C6A 1.378(3) . ?
C5A' C6A' 1.408(6) . ?
C6A C7A 1.372(4) . ?
C6A' C7A' 1.334(9) . ?
C7A C8A 1.342(4) . ?
C7A' C8A' 1.356(8) . ?
C8A C9A 1.384(3) . ?
C8A' C9A' 1.380(4) . ?
C10A N2A 1.461(2) . ?
C10A C11A 1.505(2) . ?
C11A C12A 1.378(3) . ?
C11A C16A 1.384(3) . ?
C12A C13A 1.393(3) . ?
C13A C14A 1.362(4) . ?
C14A C15A 1.351(5) . ?
C15A C16A 1.396(4) . ?
C24 N2A' 1.463(2) . ?
C24 C25 1.501(2) . ?
C25 C26 1.376(3) . ?
C25 C30 1.382(3) . ?
C26 C27 1.384(3) . ?
C27 C28 1.351(4) . ?
C28 C29 1.366(4) . ?
C29 C30 1.381(3) . ?
C31 N3 1.463(3) . ?
C31 C32 1.506(3) . ?
C32 C37 1.368(3) . ?
C32 C33 1.377(3) . ?
C33 C34 1.391(4) . ?
C34 C35 1.348(5) . ?
C35 C36 1.366(5) . ?
C36 C37 1.367(4) . ?
C38 N3 1.464(2) . ?
C38 C39 1.496(3) . ?
C39 C44 1.369(3) . ?
C39 C40 1.385(3) . ?
C40 C41 1.395(4) . ?
C41 C42 1.356(5) . ?
C42 C43 1.359(5) . ?
C43 C44 1.371(3) . ?
C45 N3 1.466(2) . ?
C45 C46 1.511(3) . ?
C46 N4 1.460(2) . ?
C47 N4 1.460(2) . ?
C47 C48 1.497(3) . ?
C48 C49 1.373(3) . ?
C48 C53 1.383(3) . ?
C49 C50 1.381(4) . ?
C50 C51 1.387(6) . ?
C51 C52 1.360(6) . ?
C52 C53 1.379(5) . ?
C54 N4 1.467(3) . ?
C54 C55 1.504(3) . ?
C55 C60 1.368(3) . ?
C55 C56 1.377(3) . ?
C56 C57 1.390(4) . ?
C57 C58 1.353(5) . ?
C58 C59 1.364(5) . ?
C59 C60 1.378(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
N2A' C1A' C1A 112.06(14) . . ?
N2A C1A C1A' 111.68(15) . . ?
N2A C3A C4A 113.54(14) . . ?
N2A' C3A' C4A' 114.14(15) . . ?
C9A' C4A' C5A' 119.5(2) . . ?
C9A' C4A' C3A' 121.7(2) . . ?
C5A' C4A' C3A' 118.8(2) . . ?
C9A C4A C5A 118.1(2) . . ?
C9A C4A C3A 120.58(19) . . ?
C5A C4A C3A 121.33(18) . . ?
C4A C5A C6A 120.6(2) . . ?
C4A' C5A' C6A' 117.7(4) . . ?
C7A C6A C5A 120.3(3) . . ?
C7A' C6A' C5A' 122.3(5) . . ?
C8A C7A C6A 119.8(2) . . ?
C6A' C7A' C8A' 119.1(4) . . ?
C7A C8A C9A 120.5(2) . . ?
C7A' C8A' C9A' 120.8(5) . . ?
C4A C9A C8A 120.8(2) . . ?
C4A' C9A' C8A' 120.5(4) . . ?
N2A C10A C11A 114.01(15) . . ?
C12A C11A C16A 118.67(19) . . ?
C12A C11A C10A 121.83(17) . . ?
C16A C11A C10A 119.43(19) . . ?
C11A C12A C13A 120.3(2) . . ?
C14A C13A C12A 120.4(3) . . ?
C15A C14A C13A 120.0(2) . . ?
C14A C15A C16A 120.7(3) . . ?
C11A C16A C15A 120.0(3) . . ?
N2A' C24 C25 113.34(14) . . ?
C26 C25 C30 118.44(19) . . ?
C26 C25 C24 120.23(19) . . ?
C30 C25 C24 121.31(18) . . ?
C25 C26 C27 120.9(2) . . ?
C28 C27 C26 120.1(2) . . ?
C27 C28 C29 119.9(2) . . ?
C28 C29 C30 120.7(3) . . ?
C29 C30 C25 119.9(2) . . ?
N3 C31 C32 111.97(17) . . ?
C37 C32 C33 118.4(2) . . ?
C37 C32 C31 121.0(2) . . ?
C33 C32 C31 120.6(2) . . ?
C32 C33 C34 119.8(3) . . ?
C35 C34 C33 120.8(3) . . ?
C34 C35 C36 119.5(3) . . ?
C35 C36 C37 120.3(3) . . ?
C36 C37 C32 121.3(3) . . ?
N3 C38 C39 113.38(16) . . ?
C44 C39 C40 118.0(2) . . ?
C44 C39 C38 120.68(19) . . ?
C40 C39 C38 121.2(2) . . ?
C39 C40 C41 120.3(3) . . ?
C42 C41 C40 120.0(3) . . ?
C41 C42 C43 119.9(3) . . ?
C42 C43 C44 120.6(3) . . ?
C39 C44 C43 121.2(2) . . ?
N3 C45 C46 112.02(17) . . ?
N4 C46 C45 112.16(16) . . ?
N4 C47 C48 113.25(16) . . ?
C49 C48 C53 119.8(2) . . ?
C49 C48 C47 120.87(19) . . ?
C53 C48 C47 119.2(2) . . ?
C48 C49 C50 120.4(3) . . ?
C49 C50 C51 119.5(4) . . ?
C52 C51 C50 119.9(3) . . ?
C51 C52 C53 120.9(3) . . ?
C52 C53 C48 119.5(3) . . ?
N4 C54 C55 112.15(17) . . ?
C60 C55 C56 118.0(2) . . ?
C60 C55 C54 121.1(2) . . ?
C56 C55 C54 120.9(2) . . ?
C55 C56 C57 120.2(3) . . ?
C58 C57 C56 120.7(3) . . ?
C57 C58 C59 119.5(3) . . ?
C58 C59 C60 120.0(3) . . ?
C55 C60 C59 121.5(3) . . ?
C10A N2A C3A 110.07(15) . . ?
C10A N2A C1A 111.09(14) . . ?
C3A N2A C1A 111.53(14) . . ?
C3A' N2A' C1A' 111.14(13) . . ?
C3A' N2A' C24 109.93(15) . . ?
C1A' N2A' C24 112.07(13) . . ?
C31 N3 C38 110.11(17) . . ?
C31 N3 C45 111.72(17) . . ?
C38 N3 C45 110.36(17) . . ?
C47 N4 C46 110.61(16) . . ?
C47 N4 C54 109.84(17) . . ?
C46 N4 C54 111.95(16) . . ?

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.034

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_gf2
_database_code_depnum_ccdc_archive 'CCDC 2109973'
loop_
_audit_author_name
_audit_author_address
'Xiaoxiao Cui'
;Liaoning University
China
;
_audit_update_record             
;
2021-09-15 deposited with the CCDC.	2022-10-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N'
_chemical_formula_weight         210.29

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.356(4)
_cell_length_b                   9.042(6)
_cell_length_c                   11.117(7)
_cell_angle_alpha                76.992(8)
_cell_angle_beta                 86.676(7)
_cell_angle_gamma                79.275(8)
_cell_volume                     611.5(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1152
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      27.23

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             226
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 240
_diffrn_standards_interval_time  '60 min'
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3282
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         27.54
_reflns_number_total             2594
_reflns_number_gt                1657
_reflns_threshold_expression     >2sigma(I)

_chemical_absolute_configuration rm

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0661P)²+0.0479P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.086(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2594
_refine_ls_number_parameters     152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1497
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3391(2) 0.07373(12) 0.12891(10) 0.0506(4) Uani 1 1 d . . .
C1 C 0.4473(3) -0.09321(15) 0.33362(12) 0.0484(4) Uani 1 1 d . . .
C2 C 0.1027(3) 0.32317(16) 0.12778(13) 0.0523(4) Uani 1 1 d . . .
C3 C 0.4309(3) -0.03503(16) 0.05186(13) 0.0546(5) Uani 1 1 d . . .
H3A H 0.517(3) -0.126(2) 0.1087(18) 0.082 Uiso 1 1 d . . .
H3B H 0.316(3) -0.073(2) 0.0172(18) 0.082 Uiso 1 1 d . . .
C4 C 0.6221(3) -0.02888(18) 0.34320(14) 0.0601(5) Uani 1 1 d . . .
H4A H 0.6358 0.0655 0.2918 0.072 Uiso 1 1 calc R . .
C5 C 0.2672(3) -0.00792(17) 0.24858(13) 0.0548(4) Uani 1 1 d . . .
H5A H 0.1817 -0.0809 0.2351 0.066 Uiso 1 1 calc R . .
H5B H 0.1758 0.0659 0.2886 0.066 Uiso 1 1 calc R . .
C6 C 0.1602(3) 0.18749(18) 0.06806(15) 0.0634(5) Uani 1 1 d . . .
H6A H 0.0362 0.1384 0.0707 0.076 Uiso 1 1 calc R . .
H6B H 0.1983 0.2234 -0.0179 0.076 Uiso 1 1 calc R . .
C7 C 0.4318(3) -0.23395(17) 0.41120(14) 0.0626(5) Uani 1 1 d . . .
H7A H 0.3146 -0.2802 0.4060 0.075 Uiso 1 1 calc R . .
C8 C 0.5888(4) -0.30625(19) 0.49625(16) 0.0765(6) Uani 1 1 d . . .
H8A H 0.5763 -0.4006 0.5481 0.092 Uiso 1 1 calc R . .
C9 C -0.0971(3) 0.3599(2) 0.17881(17) 0.0695(5) Uani 1 1 d . . .
H9A H -0.1996 0.2991 0.1776 0.083 Uiso 1 1 calc R . .
C10 C 0.2488(3) 0.41657(19) 0.13124(16) 0.0660(5) Uani 1 1 d . . .
H10A H 0.3852 0.3940 0.0976 0.079 Uiso 1 1 calc R . .
C11 C 0.7610(4) -0.2408(2) 0.50478(16) 0.0734(6) Uani 1 1 d . . .
H11A H 0.8662 -0.2898 0.5623 0.088 Uiso 1 1 calc R . .
C12 C -0.0013(5) 0.5778(2) 0.23383(18) 0.0838(8) Uani 1 1 d . . .
H12A H -0.0361 0.6635 0.2690 0.101 Uiso 1 1 calc R . .
C13 C 0.1964(4) 0.5433(2) 0.18383(19) 0.0806(7) Uani 1 1 d . . .
H13A H 0.2973 0.6054 0.1850 0.097 Uiso 1 1 calc R . .
C14 C 0.7789(3) -0.1025(2) 0.42835(16) 0.0693(5) Uani 1 1 d . . .
H14A H 0.8974 -0.0575 0.4336 0.083 Uiso 1 1 calc R . .
C15 C -0.1469(4) 0.4878(3) 0.23234(18) 0.0857(7) Uani 1 1 d . . .
H15A H -0.2821 0.5111 0.2674 0.103 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.462(2) . ?
N1 C3 1.4659(18) . ?
N1 C6 1.4661(19) . ?
C1 C4 1.367(2) . ?
C1 C7 1.384(2) . ?
C1 C5 1.506(2) . ?
C2 C10 1.374(3) . ?
C2 C9 1.374(3) . ?
C2 C6 1.500(2) . ?
C3 C3 1.505(3) 2_655 ?
C4 C14 1.383(2) . ?
C7 C8 1.380(2) . ?
C8 C11 1.355(3) . ?
C9 C15 1.394(3) . ?
C10 C13 1.379(3) . ?
C11 C14 1.365(3) . ?
C12 C15 1.344(4) . ?
C12 C13 1.355(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
C5 N1 C3 110.80(12) . . ?
C5 N1 C6 109.64(14) . . ?
C3 N1 C6 111.58(12) . . ?
C4 C1 C7 118.21(14) . . ?
C4 C1 C5 121.06(14) . . ?
C7 C1 C5 120.54(16) . . ?
C10 C2 C9 117.78(17) . . ?
C10 C2 C6 120.58(17) . . ?
C9 C2 C6 121.63(18) . . ?
N1 C3 C3 112.26(15) . 2_655 ?
C1 C4 C14 120.77(16) . . ?
N1 C5 C1 113.79(15) . . ?
N1 C6 C2 112.34(12) . . ?
C8 C7 C1 120.57(18) . . ?
C11 C8 C7 120.50(17) . . ?
C2 C9 C15 120.4(2) . . ?
C2 C10 C13 121.1(2) . . ?
C8 C11 C14 119.56(17) . . ?
C15 C12 C13 119.8(2) . . ?
C12 C13 C10 120.4(2) . . ?
C11 C14 C4 120.4(2) . . ?
C12 C15 C9 120.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.919
_diffrn_reflns_theta_full        12.50
_diffrn_measured_fraction_theta_full 0.896
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.040
