# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
# 
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data_cxc-2-me
_database_code_depnum_ccdc_archive 'CCDC 2131995'
loop_
_audit_author_name
_audit_author_address
'Yan-Biao Kang'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2022-01-02 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;
_audit_creation_date             2021-09-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C0.5 H Cl, C29 H30 N2'
_chemical_formula_sum            'C29.50 H31 Cl N2'
_chemical_formula_weight         449.01
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   22.0567(3)
_cell_length_b                   7.51330(10)
_cell_length_c                   32.5379(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.612(2)
_cell_angle_gamma                90
_cell_volume                     5079.32(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5039
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9610
_cell_measurement_theta_min      4.1090
_shelx_estimated_absorpt_T_max   0.759
_shelx_estimated_absorpt_T_min   0.712
_exptl_absorpt_coefficient_mu    1.458
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1912
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            9093
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.068
_diffrn_reflns_theta_min         4.256
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -112.00 -29.00   1.00    4.00    --  -41.05 -57.00 150.00   83
  2  ω   -126.00 -98.00   1.00    4.00    --  -41.05-178.00 -60.00   28
  3  ω   -101.00 -20.00   1.00    4.00    --  -41.05 -38.00-150.00   81
  4  ω     44.00 107.00   1.00    8.00    --   99.68-125.00 -60.00   63
  5  ω     75.00 156.00   1.00    8.00    --   99.68  45.00-150.00   81
  6  ω     23.00 126.00   1.00    8.00    --   99.68 -30.00  30.00  103
  7  ω     97.00 138.00   1.00    8.00    --   99.68  45.00-180.00   41
  8  ω     24.00 130.00   1.00    8.00    --   99.68 -77.00 -60.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0701362000
_diffrn_orient_matrix_UB_12      0.0030603000
_diffrn_orient_matrix_UB_13      -0.0006601000
_diffrn_orient_matrix_UB_21      -0.0236417000
_diffrn_orient_matrix_UB_22      0.0263600000
_diffrn_orient_matrix_UB_23      -0.0498323000
_diffrn_orient_matrix_UB_31      -0.0041191000
_diffrn_orient_matrix_UB_32      -0.2034033000
_diffrn_orient_matrix_UB_33      -0.0064974000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4002
_reflns_number_total             4699
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.841
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.00031(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4699
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0655
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0916P)²+5.0799P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1823
_refine_ls_wR_factor_ref         0.1908
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(C30) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
2. Others
 Fixed Sof: H30A(0.5) H30B(0.5)
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C22(H22A,H22B), C30(H30A,H30B)
3.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C3(H3), C24(H24), C6(H6), C8(H8), C4(H4), C17(H17), C5(H5),
 C19(H19), C18(H18), C11(H11), C9(H9), C25(H25), C10(H10), C26(H26), C27(H27)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C13(H13A,H13B,H13C), C29(H29A,H29B,H29C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.20204(7) 0.1922(2) 0.52093(5) 0.1566(6) Uani 1 1 d . . . . .
N2 N 0.52508(8) 0.4924(2) 0.63772(5) 0.0409(4) Uani 1 1 d . . . . .
C1 C 0.58348(9) 0.4750(3) 0.62542(6) 0.0417(5) Uani 1 1 d . . . . .
H1 H 0.6091 0.3809 0.6442 0.050 Uiso 1 1 calc R U . . .
N1 N 0.53609(11) 0.2443(3) 0.49587(6) 0.0657(6) Uani 1 1 d . . . . .
C15 C 0.56052(9) 0.3375(3) 0.70997(6) 0.0417(5) Uani 1 1 d . . . . .
C2 C 0.56525(9) 0.4027(3) 0.57890(6) 0.0424(5) Uani 1 1 d . . . . .
C14 C 0.53962(10) 0.5089(3) 0.68491(6) 0.0433(5) Uani 1 1 d . . . . .
H14A H 0.5016 0.5531 0.6903 0.052 Uiso 1 1 calc R U . . .
H14B H 0.5735 0.5966 0.6961 0.052 Uiso 1 1 calc R U . . .
C22 C 0.48137(9) 0.6333(3) 0.61444(6) 0.0435(5) Uani 1 1 d . . . . .
H22A H 0.4830 0.6421 0.5851 0.052 Uiso 1 1 calc R U . . .
H22B H 0.4961 0.7458 0.6290 0.052 Uiso 1 1 calc R U . . .
C7 C 0.62697(10) 0.6381(3) 0.63442(7) 0.0473(5) Uani 1 1 d . . . . .
C16 C 0.58527(10) 0.3437(3) 0.75584(7) 0.0469(5) Uani 1 1 d . . . . .
C23 C 0.41229(10) 0.6032(3) 0.61178(6) 0.0486(5) Uani 1 1 d . . . . .
C20 C 0.55681(12) 0.1749(3) 0.68940(7) 0.0536(6) Uani 1 1 d . . . . .
H20 H 0.5399 0.1697 0.6591 0.064 Uiso 1 1 calc R U . . .
C3 C 0.51199(11) 0.2936(3) 0.56157(7) 0.0525(5) Uani 1 1 d . . . . .
H3 H 0.4847 0.2706 0.5774 0.063 Uiso 1 1 calc R U . . .
C24 C 0.39237(12) 0.4405(4) 0.62276(8) 0.0603(6) Uani 1 1 d . . . . .
H24 H 0.4217 0.3475 0.6316 0.072 Uiso 1 1 calc R U . . .
C6 C 0.60298(11) 0.4303(3) 0.55311(7) 0.0551(6) Uani 1 1 d . . . . .
H6 H 0.6391 0.5033 0.5628 0.066 Uiso 1 1 calc R U . . .
C8 C 0.60999(12) 0.7873(3) 0.60771(9) 0.0592(6) Uani 1 1 d . . . . .
H8 H 0.5725 0.7849 0.5835 0.071 Uiso 1 1 calc R U . . .
C12 C 0.68476(11) 0.6415(4) 0.67043(8) 0.0583(6) Uani 1 1 d . . . . .
C4 C 0.49974(12) 0.2196(3) 0.52092(8) 0.0611(6) Uani 1 1 d . . . . .
H4 H 0.4636 0.1473 0.5102 0.073 Uiso 1 1 calc R U . . .
C17 C 0.60495(12) 0.1860(4) 0.77854(8) 0.0600(6) Uani 1 1 d . . . . .
H17 H 0.6209 0.1887 0.8089 0.072 Uiso 1 1 calc R U . . .
C28 C 0.36816(12) 0.7435(4) 0.59790(7) 0.0647(7) Uani 1 1 d . . . . .
C21 C 0.59073(14) 0.5159(4) 0.78005(8) 0.0646(7) Uani 1 1 d . . . . .
H21A H 0.6227 0.5896 0.7745 0.097 Uiso 1 1 calc R U . . .
H21B H 0.6031 0.4924 0.8108 0.097 Uiso 1 1 calc R U . . .
H21C H 0.5500 0.5760 0.7704 0.097 Uiso 1 1 calc R U . . .
C5 C 0.58665(13) 0.3485(4) 0.51269(8) 0.0664(7) Uani 1 1 d . . . . .
H5 H 0.6132 0.3684 0.4962 0.080 Uiso 1 1 calc R U . . .
C19 C 0.57756(15) 0.0202(3) 0.71270(9) 0.0686(7) Uani 1 1 d . . . . .
H19 H 0.5754 -0.0877 0.6983 0.082 Uiso 1 1 calc R U . . .
C18 C 0.60150(14) 0.0270(4) 0.75758(9) 0.0696(7) Uani 1 1 d . . . . .
H18 H 0.6153 -0.0767 0.7736 0.084 Uiso 1 1 calc R U . . .
C13 C 0.70953(12) 0.4837(5) 0.69997(9) 0.0768(8) Uani 1 1 d . . . . .
H13A H 0.6786 0.4508 0.7135 0.115 Uiso 1 1 calc R U . . .
H13B H 0.7495 0.5145 0.7221 0.115 Uiso 1 1 calc R U . . .
H13C H 0.7163 0.3854 0.6831 0.115 Uiso 1 1 calc R U . . .
C11 C 0.72121(13) 0.7967(5) 0.67792(11) 0.0791(9) Uani 1 1 d . . . . .
H11 H 0.7592 0.8007 0.7017 0.095 Uiso 1 1 calc R U . . .
C9 C 0.64774(15) 0.9396(4) 0.61634(12) 0.0786(8) Uani 1 1 d . . . . .
H9 H 0.6355 1.0386 0.5983 0.094 Uiso 1 1 calc R U . . .
C25 C 0.32904(14) 0.4149(5) 0.62068(9) 0.0845(10) Uani 1 1 d . . . . .
H25 H 0.3160 0.3055 0.6281 0.101 Uiso 1 1 calc R U . . .
C10 C 0.70357(16) 0.9429(5) 0.65192(13) 0.0887(10) Uani 1 1 d . . . . .
H10 H 0.7291 1.0446 0.6581 0.106 Uiso 1 1 calc R U . . .
C29 C 0.38814(17) 0.9215(4) 0.58587(11) 0.0895(10) Uani 1 1 d . . . . .
H29A H 0.4182 0.9758 0.6113 0.134 Uiso 1 1 calc R U . . .
H29B H 0.3510 0.9964 0.5747 0.134 Uiso 1 1 calc R U . . .
H29C H 0.4080 0.9061 0.5640 0.134 Uiso 1 1 calc R U . . .
C26 C 0.28605(14) 0.5522(7) 0.60756(11) 0.1024(14) Uani 1 1 d . . . . .
H26 H 0.2438 0.5368 0.6066 0.123 Uiso 1 1 calc R U . . .
C27 C 0.30504(14) 0.7121(7) 0.59580(10) 0.0924(12) Uani 1 1 d . . . . .
H27 H 0.2748 0.8026 0.5861 0.111 Uiso 1 1 calc R U . . .
C30 C 0.2500 0.3194(10) 0.5000 0.165(3) Uani 1 2 d S TU P . .
H30A H 0.2228 0.3955 0.4771 0.198 Uiso 0.5 1 calc R U P . .
H30B H 0.2772 0.3955 0.5229 0.198 Uiso 0.5 1 calc R U 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
Cl1 C30 1.726(4) . ?
N2 C1 1.477(2) . ?
N2 C14 1.465(2) . ?
N2 C22 1.461(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.530(3) . ?
C1 C7 1.523(3) . ?
N1 C4 1.334(3) . ?
N1 C5 1.322(3) . ?
C15 C14 1.511(3) . ?
C15 C16 1.407(3) . ?
C15 C20 1.383(3) . ?
C2 C3 1.387(3) . ?
C2 C6 1.381(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.514(3) . ?
C7 C8 1.391(3) . ?
C7 C12 1.413(3) . ?
C16 C17 1.386(3) . ?
C16 C21 1.499(3) . ?
C23 C24 1.386(4) . ?
C23 C28 1.402(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.379(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.389(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.386(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.387(4) . ?
C12 C13 1.508(4) . ?
C12 C11 1.390(4) . ?
C4 H4 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.365(4) . ?
C28 C29 1.501(5) . ?
C28 C27 1.391(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C5 H5 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.377(4) . ?
C18 H18 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C10 1.361(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.369(6) . ?
C10 H10 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C26 H26 0.9300 . ?
C26 C27 1.369(6) . ?
C27 H27 0.9300 . ?
C30 Cl1 1.726(4) 2_556 ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 N2 C1 112.81(15) . . ?
C22 N2 C1 114.04(15) . . ?
C22 N2 C14 110.89(15) . . ?
N2 C1 H1 105.5 . . ?
N2 C1 C2 109.64(15) . . ?
N2 C1 C7 115.27(16) . . ?
C2 C1 H1 105.5 . . ?
C7 C1 H1 105.5 . . ?
C7 C1 C2 114.56(17) . . ?
C5 N1 C4 115.2(2) . . ?
C16 C15 C14 118.94(18) . . ?
C20 C15 C14 122.29(17) . . ?
C20 C15 C16 118.76(19) . . ?
C3 C2 C1 121.18(18) . . ?
C6 C2 C1 122.39(19) . . ?
C6 C2 C3 116.25(19) . . ?
N2 C14 C15 114.41(16) . . ?
N2 C14 H14A 108.7 . . ?
N2 C14 H14B 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
N2 C22 H22A 108.9 . . ?
N2 C22 H22B 108.9 . . ?
N2 C22 C23 113.45(17) . . ?
H22A C22 H22B 107.7 . . ?
C23 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
C8 C7 C1 120.56(19) . . ?
C8 C7 C12 118.8(2) . . ?
C12 C7 C1 120.6(2) . . ?
C15 C16 C21 121.3(2) . . ?
C17 C16 C15 118.5(2) . . ?
C17 C16 C21 120.13(19) . . ?
C24 C23 C22 121.1(2) . . ?
C24 C23 C28 120.0(2) . . ?
C28 C23 C22 118.9(2) . . ?
C15 C20 H20 119.2 . . ?
C19 C20 C15 121.6(2) . . ?
C19 C20 H20 119.2 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.1 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.7(3) . . ?
C25 C24 H24 119.7 . . ?
C2 C6 H6 120.3 . . ?
C2 C6 C5 119.5(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.4(3) . . ?
C9 C8 H8 119.3 . . ?
C7 C12 C13 123.2(2) . . ?
C11 C12 C7 117.9(3) . . ?
C11 C12 C13 118.9(2) . . ?
N1 C4 C3 124.5(2) . . ?
N1 C4 H4 117.7 . . ?
C3 C4 H4 117.7 . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.8(2) . . ?
C18 C17 H17 119.1 . . ?
C23 C28 C29 121.4(2) . . ?
C27 C28 C23 117.6(3) . . ?
C27 C28 C29 121.0(3) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C5 C6 124.8(2) . . ?
N1 C5 H5 117.6 . . ?
C6 C5 H5 117.6 . . ?
C20 C19 H19 120.3 . . ?
C18 C19 C20 119.4(2) . . ?
C18 C19 H19 120.3 . . ?
C17 C18 C19 120.0(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C11 H11 118.7 . . ?
C10 C11 C12 122.7(3) . . ?
C10 C11 H11 118.7 . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(3) . . ?
C10 C9 H9 120.3 . . ?
C24 C25 H25 120.3 . . ?
C26 C25 C24 119.4(3) . . ?
C26 C25 H25 120.3 . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C25 C26 H26 119.9 . . ?
C27 C26 C25 120.3(3) . . ?
C27 C26 H26 119.9 . . ?
C28 C27 H27 119.0 . . ?
C26 C27 C28 122.0(3) . . ?
C26 C27 H27 119.0 . . ?
Cl1 C30 Cl1 112.7(4) 2_556 . ?
Cl1 C30 H30A 109.0 . . ?
Cl1 C30 H30A 109.0 2_556 . ?
Cl1 C30 H30B 109.0 2_556 . ?
Cl1 C30 H30B 109.0 . . ?
H30A C30 H30B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 C2 C3 -28.6(3) . . . . ?
N2 C1 C2 C6 156.4(2) . . . . ?
N2 C1 C7 C8 -75.5(2) . . . . ?
N2 C1 C7 C12 103.6(2) . . . . ?
N2 C22 C23 C24 -12.2(3) . . . . ?
N2 C22 C23 C28 167.83(18) . . . . ?
C1 N2 C14 C15 -74.4(2) . . . . ?
C1 N2 C22 C23 155.37(16) . . . . ?
C1 C2 C3 C4 -175.0(2) . . . . ?
C1 C2 C6 C5 174.5(2) . . . . ?
C1 C7 C8 C9 177.5(2) . . . . ?
C1 C7 C12 C13 4.5(3) . . . . ?
C1 C7 C12 C11 -177.6(2) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?
C15 C20 C19 C18 1.2(4) . . . . ?
C2 C1 C7 C8 53.2(3) . . . . ?
C2 C1 C7 C12 -127.8(2) . . . . ?
C2 C3 C4 N1 0.2(4) . . . . ?
C2 C6 C5 N1 0.7(4) . . . . ?
C14 N2 C1 C2 162.84(16) . . . . ?
C14 N2 C1 C7 -66.1(2) . . . . ?
C14 N2 C22 C23 -76.0(2) . . . . ?
C14 C15 C16 C17 -179.3(2) . . . . ?
C14 C15 C16 C21 0.5(3) . . . . ?
C14 C15 C20 C19 178.4(2) . . . . ?
C22 N2 C1 C2 -69.5(2) . . . . ?
C22 N2 C1 C7 61.5(2) . . . . ?
C22 N2 C14 C15 156.27(17) . . . . ?
C22 C23 C24 C25 179.3(2) . . . . ?
C22 C23 C28 C29 -0.2(3) . . . . ?
C22 C23 C28 C27 -180.0(2) . . . . ?
C7 C1 C2 C3 -160.0(2) . . . . ?
C7 C1 C2 C6 25.0(3) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
C7 C12 C11 C10 -0.4(4) . . . . ?
C16 C15 C14 N2 170.08(17) . . . . ?
C16 C15 C20 C19 -0.9(4) . . . . ?
C16 C17 C18 C19 -0.4(4) . . . . ?
C23 C24 C25 C26 0.1(4) . . . . ?
C23 C28 C27 C26 1.3(4) . . . . ?
C20 C15 C14 N2 -9.2(3) . . . . ?
C20 C15 C16 C17 0.0(3) . . . . ?
C20 C15 C16 C21 179.8(2) . . . . ?
C20 C19 C18 C17 -0.5(4) . . . . ?
C3 C2 C6 C5 -0.7(3) . . . . ?
C24 C23 C28 C29 179.8(2) . . . . ?
C24 C23 C28 C27 0.1(3) . . . . ?
C24 C25 C26 C27 1.3(5) . . . . ?
C6 C2 C3 C4 0.3(3) . . . . ?
C8 C7 C12 C13 -176.5(2) . . . . ?
C8 C7 C12 C11 1.4(3) . . . . ?
C8 C9 C10 C11 0.5(5) . . . . ?
C12 C7 C8 C9 -1.5(3) . . . . ?
C12 C11 C10 C9 -0.5(5) . . . . ?
C4 N1 C5 C6 -0.3(4) . . . . ?
C28 C23 C24 C25 -0.8(3) . . . . ?
C21 C16 C17 C18 -179.1(3) . . . . ?
C5 N1 C4 C3 -0.2(4) . . . . ?
C13 C12 C11 C10 177.6(3) . . . . ?
C25 C26 C27 C28 -2.0(5) . . . . ?
C29 C28 C27 C26 -178.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.410
_oxdiff_exptl_absorpt_empirical_full_min 0.684
####################################################################### 
# 
# 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_cxc-4-me
_database_code_depnum_ccdc_archive 'CCDC 2131996'
loop_
_audit_author_name
_audit_author_address
'Yan-Biao Kang'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2022-01-02 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;
_audit_creation_date             2021-09-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C27 H26 N2 O'
_chemical_formula_sum            'C27 H26 N2 O'
_chemical_formula_weight         394.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N2
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.8864(3)
_cell_length_b                   9.9577(4)
_cell_length_c                   15.3148(4)
_cell_angle_alpha                75.304(3)
_cell_angle_beta                 85.678(3)
_cell_angle_gamma                67.535(4)
_cell_volume                     1074.74(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5113
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0250
_cell_measurement_theta_min      4.9670
_shelx_estimated_absorpt_T_max   0.903
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7116
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.053
_diffrn_reflns_theta_min         4.956
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00 -17.00   1.00    2.00    --  -40.80 -57.00 -90.00   89
  2  ω   -114.00 -39.00   1.00    2.00    --  -40.80 178.00  60.00   75
  3  ω    -66.00  32.00   1.00    2.00    --  -40.80  57.00  60.00   98
  4  ω     66.00  91.00   1.00    2.00    --   40.80 178.00 -60.00   25
  5  ω     74.00 103.00   1.00    4.00    --   99.68 -94.00 -30.00   29
  6  ω    112.00 165.00   1.00    4.00    --   99.68 125.00 -60.00   53
  7  ω     33.00  99.00   1.00    4.00    --   99.68 -77.00  30.00   66
  8  ω     83.00 113.00   1.00    4.00    --   99.68-125.00 150.00   30
  9  ω     29.00 127.00   1.00    4.00    --   99.68 -61.00-120.00   98
 10  ω     25.00  52.00   1.00    4.00    --   99.68 -94.00 -30.00   27
 11  ω     38.00  65.00   1.00    4.00    --   99.68-125.00 150.00   27
 12  ω    130.00 168.00   1.00    4.00    --   99.68  77.00-150.00   38
 13  ω     38.00  80.00   1.00    4.00    --   99.68-125.00-180.00   42
 14  ω     84.00 112.00   1.00    4.00    --   99.68-125.00-180.00   28
 15  ω     87.00 171.00   1.00    4.00    --   99.68  45.00  30.00   84
 16  ω     17.00 106.00   1.00    4.00    --   99.68 -94.00-120.00   89
 17  ω     51.00 174.00   1.00    4.00    --   99.68   0.00   0.00  123
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1411734000
_diffrn_orient_matrix_UB_12      0.0751547000
_diffrn_orient_matrix_UB_13      -0.0107522000
_diffrn_orient_matrix_UB_21      -0.1565229000
_diffrn_orient_matrix_UB_22      0.1521747000
_diffrn_orient_matrix_UB_23      -0.0020181000
_diffrn_orient_matrix_UB_31      0.0167521000
_diffrn_orient_matrix_UB_32      -0.0315867000
_diffrn_orient_matrix_UB_33      0.1034487000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3634
_reflns_number_total             3956
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0120(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3956
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0623P)²+0.1556P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1142
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C1(H1)
1.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C21(H21A,H21B)
1.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C12(H12), C20(H20), C6(H6), C8(H8), C16(H16), C11(H11), C23(H23),
 C27(H27), C9(H9), C5(H5), C10(H10), C17(H17), C26(H26), C25(H25), C24(H24),
 C19(H19), C18(H18)
1.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.78227(13) 0.81452(11) 0.50376(6) 0.0617(3) Uani 1 1 d . . . . .
N2 N 0.71648(12) 0.43473(10) 0.77028(6) 0.0392(2) Uani 1 1 d . . . . .
N1 N 1.08451(15) 0.65211(14) 0.52892(7) 0.0553(3) Uani 1 1 d . . . . .
C2 C 0.97177(15) 0.47405(13) 0.67588(7) 0.0402(3) Uani 1 1 d . . . . .
C7 C 1.03966(15) 0.31477(13) 0.83735(8) 0.0404(3) Uani 1 1 d . . . . .
C15 C 0.63102(14) 0.22446(12) 0.75374(8) 0.0404(3) Uani 1 1 d . . . . .
C1 C 0.91535(15) 0.37045(13) 0.75342(7) 0.0395(3) Uani 1 1 d . . . . .
H1 H 0.9342 0.2811 0.7321 0.047 Uiso 1 1 calc R U . . .
C22 C 0.46170(16) 0.64112(13) 0.81687(8) 0.0437(3) Uani 1 1 d . . . . .
C14 C 0.64242(16) 0.32061(14) 0.81289(8) 0.0439(3) Uani 1 1 d . . . . .
H14A H 0.5203 0.3700 0.8336 0.053 Uiso 1 1 calc R U . . .
H14B H 0.7183 0.2560 0.8657 0.053 Uiso 1 1 calc R U . . .
C3 C 0.84766(16) 0.60239(14) 0.62333(8) 0.0447(3) Uani 1 1 d . . . . .
H3 H 0.7230 0.6322 0.6352 0.054 Uiso 1 1 calc R U . . .
C12 C 1.09144(17) 0.41042(14) 0.87139(8) 0.0464(3) Uani 1 1 d . . . . .
H12 H 1.0543 0.5110 0.8411 0.056 Uiso 1 1 calc R U . . .
C4 C 0.91150(17) 0.68762(14) 0.55161(8) 0.0464(3) Uani 1 1 d . . . . .
C21 C 0.66603(16) 0.55121(14) 0.82043(8) 0.0446(3) Uani 1 1 d . . . . .
H21A H 0.7295 0.6184 0.7956 0.054 Uiso 1 1 calc R U . . .
H21B H 0.7064 0.5047 0.8830 0.054 Uiso 1 1 calc R U . . .
C20 C 0.57686(18) 0.10542(14) 0.79280(10) 0.0525(3) Uani 1 1 d . . . . .
H20 H 0.5523 0.0866 0.8541 0.063 Uiso 1 1 calc R U . . .
C6 C 1.15652(17) 0.43409(16) 0.65250(9) 0.0510(3) Uani 1 1 d . . . . .
H6 H 1.2457 0.3477 0.6859 0.061 Uiso 1 1 calc R U . . .
C8 C 1.10008(18) 0.16462(14) 0.88310(9) 0.0516(3) Uani 1 1 d . . . . .
H8 H 1.0682 0.0984 0.8610 0.062 Uiso 1 1 calc R U . . .
C16 C 0.66492(17) 0.25062(16) 0.66219(9) 0.0519(3) Uani 1 1 d . . . . .
H16 H 0.6983 0.3311 0.6342 0.062 Uiso 1 1 calc R U . . .
C11 C 1.19746(19) 0.35791(17) 0.94969(9) 0.0550(3) Uani 1 1 d . . . . .
H11 H 1.2301 0.4235 0.9720 0.066 Uiso 1 1 calc R U . . .
C23 C 0.37544(19) 0.68343(15) 0.89330(10) 0.0539(3) Uani 1 1 d . . . . .
H23 H 0.4437 0.6549 0.9464 0.065 Uiso 1 1 calc R U . . .
C27 C 0.35618(19) 0.68517(17) 0.73887(10) 0.0569(3) Uani 1 1 d . . . . .
H27 H 0.4111 0.6574 0.6869 0.068 Uiso 1 1 calc R U . . .
C9 C 1.2075(2) 0.11207(16) 0.96150(10) 0.0622(4) Uani 1 1 d . . . . .
H9 H 1.2473 0.0112 0.9915 0.075 Uiso 1 1 calc R U . . .
C5 C 1.20355(18) 0.52418(18) 0.57984(9) 0.0599(4) Uani 1 1 d . . . . .
H5 H 1.3266 0.4949 0.5646 0.072 Uiso 1 1 calc R U . . .
C10 C 1.25508(19) 0.20900(18) 0.99487(9) 0.0607(4) Uani 1 1 d . . . . .
H10 H 1.3259 0.1742 1.0477 0.073 Uiso 1 1 calc R U . . .
C17 C 0.6496(2) 0.1583(2) 0.61211(11) 0.0680(4) Uani 1 1 d . . . . .
H17 H 0.6745 0.1764 0.5509 0.082 Uiso 1 1 calc R U . . .
C26 C 0.1702(2) 0.76983(17) 0.73716(12) 0.0667(4) Uani 1 1 d . . . . .
H26 H 0.1012 0.7991 0.6841 0.080 Uiso 1 1 calc R U . . .
C25 C 0.0866(2) 0.81092(17) 0.81387(13) 0.0709(4) Uani 1 1 d . . . . .
H25 H -0.0385 0.8677 0.8128 0.085 Uiso 1 1 calc R U . . .
C24 C 0.1893(2) 0.76735(18) 0.89163(12) 0.0689(4) Uani 1 1 d . . . . .
H24 H 0.1335 0.7944 0.9436 0.083 Uiso 1 1 calc R U . . .
C19 C 0.5590(2) 0.01502(17) 0.74232(13) 0.0699(4) Uani 1 1 d . . . . .
H19 H 0.5206 -0.0630 0.7694 0.084 Uiso 1 1 calc R U . . .
C18 C 0.5979(2) 0.0400(2) 0.65159(14) 0.0752(5) Uani 1 1 d . . . . .
H18 H 0.5893 -0.0224 0.6176 0.090 Uiso 1 1 calc R U . . .
C13 C 0.8438(2) 0.90620(19) 0.43139(11) 0.0714(4) Uani 1 1 d . . . . .
H13A H 0.8985 0.8515 0.3865 0.107 Uiso 1 1 calc R U . . .
H13B H 0.9328 0.9336 0.4542 0.107 Uiso 1 1 calc R U . . .
H13C H 0.7412 0.9950 0.4049 0.107 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
O1 C4 1.3531(16) . ?
O1 C13 1.4286(17) . ?
N2 C1 1.4805(14) . ?
N2 C14 1.4601(14) . ?
N2 C21 1.4651(15) . ?
N1 C4 1.3152(17) . ?
N1 C5 1.3433(18) . ?
C2 C1 1.5238(15) . ?
C2 C3 1.3711(17) . ?
C2 C6 1.4000(16) . ?
C7 C1 1.5276(16) . ?
C7 C12 1.3882(17) . ?
C7 C8 1.3884(17) . ?
C15 C14 1.5045(16) . ?
C15 C20 1.3907(17) . ?
C15 C16 1.3844(17) . ?
C1 H1 0.9800 . ?
C22 C21 1.5124(16) . ?
C22 C23 1.3861(18) . ?
C22 C27 1.3846(19) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C3 H3 0.9300 . ?
C3 C4 1.3965(17) . ?
C12 H12 0.9300 . ?
C12 C11 1.3817(18) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C20 H20 0.9300 . ?
C20 C19 1.376(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.3661(19) . ?
C8 H8 0.9300 . ?
C8 C9 1.389(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.3799(19) . ?
C11 H11 0.9300 . ?
C11 C10 1.377(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.382(2) . ?
C27 H27 0.9300 . ?
C27 C26 1.383(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(2) . ?
C5 H5 0.9300 . ?
C10 H10 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.374(3) . ?
C26 H26 0.9300 . ?
C26 C25 1.380(2) . ?
C25 H25 0.9300 . ?
C25 C24 1.370(3) . ?
C24 H24 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.380(3) . ?
C18 H18 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
C4 O1 C13 117.20(11) . . ?
C14 N2 C1 112.82(9) . . ?
C14 N2 C21 110.62(9) . . ?
C21 N2 C1 113.78(9) . . ?
C4 N1 C5 115.74(11) . . ?
C3 C2 C1 122.90(10) . . ?
C3 C2 C6 117.39(11) . . ?
C6 C2 C1 119.59(11) . . ?
C12 C7 C1 122.13(10) . . ?
C12 C7 C8 118.25(11) . . ?
C8 C7 C1 119.60(11) . . ?
C20 C15 C14 117.95(11) . . ?
C16 C15 C14 123.90(11) . . ?
C16 C15 C20 118.10(12) . . ?
N2 C1 C2 111.59(9) . . ?
N2 C1 C7 114.80(9) . . ?
N2 C1 H1 105.5 . . ?
C2 C1 C7 113.05(9) . . ?
C2 C1 H1 105.5 . . ?
C7 C1 H1 105.5 . . ?
C23 C22 C21 119.69(11) . . ?
C27 C22 C21 122.17(11) . . ?
C27 C22 C23 118.13(12) . . ?
N2 C14 C15 115.34(9) . . ?
N2 C14 H14A 108.4 . . ?
N2 C14 H14B 108.4 . . ?
C15 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
H14A C14 H14B 107.5 . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.90(11) . . ?
C4 C3 H3 120.6 . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.78(12) . . ?
C11 C12 H12 119.6 . . ?
O1 C4 C3 115.84(11) . . ?
N1 C4 O1 119.66(11) . . ?
N1 C4 C3 124.51(12) . . ?
N2 C21 C22 112.68(9) . . ?
N2 C21 H21A 109.1 . . ?
N2 C21 H21B 109.1 . . ?
C22 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C15 C20 H20 119.4 . . ?
C19 C20 C15 121.16(14) . . ?
C19 C20 H20 119.4 . . ?
C2 C6 H6 120.6 . . ?
C5 C6 C2 118.88(12) . . ?
C5 C6 H6 120.6 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.80(13) . . ?
C9 C8 H8 119.6 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.55(13) . . ?
C17 C16 H16 119.7 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.38(13) . . ?
C10 C11 H11 119.8 . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 120.92(14) . . ?
C24 C23 H23 119.5 . . ?
C22 C27 H27 119.6 . . ?
C26 C27 C22 120.89(14) . . ?
C26 C27 H27 119.6 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.07(13) . . ?
C10 C9 H9 120.0 . . ?
N1 C5 C6 124.56(12) . . ?
N1 C5 H5 117.7 . . ?
C6 C5 H5 117.7 . . ?
C11 C10 H10 120.1 . . ?
C9 C10 C11 119.70(13) . . ?
C9 C10 H10 120.1 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.85(15) . . ?
C18 C17 H17 119.6 . . ?
C27 C26 H26 119.9 . . ?
C25 C26 C27 120.19(15) . . ?
C25 C26 H26 119.9 . . ?
C26 C25 H25 120.3 . . ?
C24 C25 C26 119.48(14) . . ?
C24 C25 H25 120.3 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.39(14) . . ?
C25 C24 H24 119.8 . . ?
C20 C19 H19 120.0 . . ?
C20 C19 C18 120.10(14) . . ?
C18 C19 H19 120.0 . . ?
C17 C18 C19 119.22(14) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C2 C3 C4 O1 -178.61(11) . . . . ?
C2 C3 C4 N1 1.47(19) . . . . ?
C2 C6 C5 N1 1.2(2) . . . . ?
C7 C12 C11 C10 0.6(2) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C15 C20 C19 C18 1.1(2) . . . . ?
C15 C16 C17 C18 0.9(2) . . . . ?
C1 N2 C14 C15 -70.21(12) . . . . ?
C1 N2 C21 C22 165.77(9) . . . . ?
C1 C2 C3 C4 -177.68(10) . . . . ?
C1 C2 C6 C5 176.58(12) . . . . ?
C1 C7 C12 C11 177.15(11) . . . . ?
C1 C7 C8 C9 -177.57(11) . . . . ?
C22 C23 C24 C25 -0.3(2) . . . . ?
C22 C27 C26 C25 -0.4(2) . . . . ?
C14 N2 C1 C2 154.83(9) . . . . ?
C14 N2 C1 C7 -74.88(12) . . . . ?
C14 N2 C21 C22 -66.02(13) . . . . ?
C14 C15 C20 C19 178.37(12) . . . . ?
C14 C15 C16 C17 -179.23(12) . . . . ?
C3 C2 C1 N2 -6.43(15) . . . . ?
C3 C2 C1 C7 -137.62(11) . . . . ?
C3 C2 C6 C5 0.40(19) . . . . ?
C12 C7 C1 N2 -83.28(13) . . . . ?
C12 C7 C1 C2 46.29(14) . . . . ?
C12 C7 C8 C9 0.82(19) . . . . ?
C12 C11 C10 C9 0.3(2) . . . . ?
C4 N1 C5 C6 -1.5(2) . . . . ?
C21 N2 C1 C2 -78.10(11) . . . . ?
C21 N2 C1 C7 52.19(13) . . . . ?
C21 N2 C14 C15 161.06(10) . . . . ?
C21 C22 C23 C24 179.12(12) . . . . ?
C21 C22 C27 C26 -178.74(12) . . . . ?
C20 C15 C14 N2 174.46(10) . . . . ?
C20 C15 C16 C17 -1.61(19) . . . . ?
C20 C19 C18 C17 -1.8(2) . . . . ?
C6 C2 C1 N2 177.61(10) . . . . ?
C6 C2 C1 C7 46.41(14) . . . . ?
C6 C2 C3 C4 -1.64(17) . . . . ?
C8 C7 C1 N2 95.04(13) . . . . ?
C8 C7 C1 C2 -135.39(11) . . . . ?
C8 C7 C12 C11 -1.19(18) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C16 C15 C14 N2 -7.92(17) . . . . ?
C16 C15 C20 C19 0.60(19) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C23 C22 C21 N2 140.54(11) . . . . ?
C23 C22 C27 C26 0.4(2) . . . . ?
C27 C22 C21 N2 -40.32(16) . . . . ?
C27 C22 C23 C24 -0.1(2) . . . . ?
C27 C26 C25 C24 0.1(2) . . . . ?
C5 N1 C4 O1 -179.84(12) . . . . ?
C5 N1 C4 C3 0.1(2) . . . . ?
C26 C25 C24 C23 0.3(2) . . . . ?
C13 O1 C4 N1 -1.65(19) . . . . ?
C13 O1 C4 C3 178.43(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.408
_oxdiff_exptl_absorpt_empirical_full_min 0.636
