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

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

data_t
_database_code_depnum_ccdc_archive 'CCDC 2071511'
loop_
_audit_author_name
_audit_author_address
'Xinyu Chen'
;Huaibei Normal University
China
;
_audit_update_record             
;
2021-03-19 deposited with the CCDC.	2021-06-15 downloaded from the CCDC.
;
_audit_creation_date             2020-12-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H21 N'
_chemical_formula_sum            'C27 H21 N'
_chemical_formula_weight         359.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.0099(13)
_cell_length_b                   10.3660(15)
_cell_length_c                   11.4985(16)
_cell_angle_alpha                67.411(2)
_cell_angle_beta                 86.553(2)
_cell_angle_gamma                87.881(2)
_cell_volume                     989.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1543
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.42
_cell_measurement_theta_min      2.90
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6558
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0515 before and 0.0265 after correction.
The Ratio of minimum to maximum transmission is 0.8796.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6052
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.735
_diffrn_reflns_theta_min         2.128
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2652
_reflns_number_total             4351
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4351
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0582
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0767P)²+0.1995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1679
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.38954(17) 0.61721(16) 0.77851(15) 0.0417(4) Uani 1 1 d . . . . .
C1 C 0.3621(2) 0.7425(2) 0.5437(2) 0.0497(5) Uani 1 1 d . . . . .
C2 C 0.3235(3) 0.6811(3) 0.4624(2) 0.0673(7) Uani 1 1 d . . . . .
H2 H 0.3630 0.5953 0.4668 0.081 Uiso 1 1 calc R . . . .
C3 C 0.2214(3) 0.7562(5) 0.3733(3) 0.0930(11) Uani 1 1 d . . . . .
H3 H 0.1927 0.7200 0.3156 0.112 Uiso 1 1 calc R . . . .
C4 C 0.1622(3) 0.8824(5) 0.3686(3) 0.0995(12) Uani 1 1 d . . . . .
H4 H 0.0952 0.9292 0.3072 0.119 Uiso 1 1 calc R . . . .
C5 C 0.1987(3) 0.9420(3) 0.4518(3) 0.0825(9) Uani 1 1 d . . . . .
H5 H 0.1570 1.0264 0.4494 0.099 Uiso 1 1 calc R . . . .
C6 C 0.3013(2) 0.8679(2) 0.5390(2) 0.0580(6) Uani 1 1 d . . . . .
C7 C 0.3772(2) 0.8657(2) 0.6545(2) 0.0535(6) Uani 1 1 d . . . . .
H7 H 0.4450 0.9424 0.6410 0.064 Uiso 1 1 calc R . . . .
C8 C 0.4524(2) 0.7218(2) 0.65844(19) 0.0426(5) Uani 1 1 d . . . . .
C9 C 0.6200(2) 0.7082(2) 0.64559(18) 0.0430(5) Uani 1 1 d . . . . .
C10 C 0.6839(2) 0.6798(2) 0.5450(2) 0.0556(6) Uani 1 1 d . . . . .
H10 H 0.6234 0.6742 0.4845 0.067 Uiso 1 1 calc R . . . .
C11 C 0.8360(3) 0.6598(3) 0.5327(2) 0.0668(7) Uani 1 1 d . . . . .
H11 H 0.8766 0.6411 0.4644 0.080 Uiso 1 1 calc R . . . .
C12 C 0.9260(2) 0.6675(3) 0.6210(2) 0.0626(7) Uani 1 1 d . . . . .
H12 H 1.0279 0.6522 0.6140 0.075 Uiso 1 1 calc R . . . .
C13 C 0.8655(2) 0.6980(2) 0.7206(2) 0.0556(6) Uani 1 1 d . . . . .
H13 H 0.9279 0.7039 0.7798 0.067 Uiso 1 1 calc R . . . .
C14 C 0.7127(2) 0.7201(2) 0.73474(19) 0.0478(5) Uani 1 1 d . . . . .
C15 C 0.6553(3) 0.7601(3) 0.8419(2) 0.0654(7) Uani 1 1 d . . . . .
H15A H 0.6057 0.8495 0.8089 0.098 Uiso 1 1 calc GR . . . .
H15B H 0.7369 0.7652 0.8898 0.098 Uiso 1 1 calc GR . . . .
H15C H 0.5865 0.6912 0.8953 0.098 Uiso 1 1 calc GR . . . .
C16 C 0.2771(2) 0.8234(2) 0.7716(2) 0.0500(5) Uani 1 1 d . . . . .
C17 C 0.1842(3) 0.9032(3) 0.8177(3) 0.0677(7) Uani 1 1 d . . . . .
H17 H 0.1802 0.9998 0.7757 0.081 Uiso 1 1 calc R . . . .
C18 C 0.0967(3) 0.8389(3) 0.9273(3) 0.0770(8) Uani 1 1 d . . . . .
H18 H 0.0348 0.8924 0.9595 0.092 Uiso 1 1 calc R . . . .
C19 C 0.1020(3) 0.6959(3) 0.9881(2) 0.0653(7) Uani 1 1 d . . . . .
H19 H 0.0430 0.6537 1.0614 0.078 Uiso 1 1 calc R . . . .
C20 C 0.1933(2) 0.6128(2) 0.9426(2) 0.0499(5) Uani 1 1 d . . . . .
H20 H 0.1949 0.5161 0.9838 0.060 Uiso 1 1 calc R . . . .
C21 C 0.2819(2) 0.6782(2) 0.83404(19) 0.0423(5) Uani 1 1 d . . . . .
C22 C 0.3926(2) 0.4721(2) 0.80082(17) 0.0400(5) Uani 1 1 d . . . . .
C23 C 0.2661(2) 0.4062(2) 0.7884(2) 0.0554(6) Uani 1 1 d . . . . .
H23 H 0.1790 0.4577 0.7625 0.066 Uiso 1 1 calc R . . . .
C24 C 0.2696(3) 0.2651(3) 0.8143(3) 0.0700(7) Uani 1 1 d . . . . .
H24 H 0.1847 0.2217 0.8059 0.084 Uiso 1 1 calc R . . . .
C25 C 0.3978(3) 0.1878(3) 0.8524(2) 0.0694(7) Uani 1 1 d . . . . .
H25 H 0.3996 0.0924 0.8701 0.083 Uiso 1 1 calc R . . . .
C26 C 0.5228(3) 0.2522(2) 0.8642(2) 0.0642(7) Uani 1 1 d . . . . .
H26 H 0.6098 0.2002 0.8892 0.077 Uiso 1 1 calc R . . . .
C27 C 0.5210(2) 0.3938(2) 0.8392(2) 0.0514(5) Uani 1 1 d . . . . .
H27 H 0.6062 0.4364 0.8483 0.062 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 C8 1.485(2) . ?
N1 C21 1.392(2) . ?
N1 C22 1.425(2) . ?
C1 C2 1.383(3) . ?
C1 C6 1.375(3) . ?
C1 C8 1.532(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.396(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(3) . ?
C6 C7 1.522(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.601(3) . ?
C7 C16 1.499(3) . ?
C8 C9 1.515(3) . ?
C9 C10 1.388(3) . ?
C9 C14 1.404(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.364(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.397(3) . ?
C14 C15 1.502(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.379(3) . ?
C16 C21 1.396(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.375(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.390(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.388(3) . ?
C22 C23 1.393(3) . ?
C22 C27 1.381(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.376(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.375(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.370(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.383(3) . ?
C27 H27 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 N1 C8 110.90(15) . . ?
C21 N1 C22 123.01(16) . . ?
C22 N1 C8 120.98(15) . . ?
C2 C1 C8 144.1(2) . . ?
C6 C1 C2 122.2(2) . . ?
C6 C1 C8 93.65(19) . . ?
C1 C2 H2 122.1 . . ?
C1 C2 C3 115.7(3) . . ?
C3 C2 H2 122.1 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 118.8 . . ?
C3 C4 C5 122.4(3) . . ?
C5 C4 H4 118.8 . . ?
C4 C5 H5 122.2 . . ?
C4 C5 C6 115.6(3) . . ?
C6 C5 H5 122.2 . . ?
C1 C6 C5 122.3(3) . . ?
C1 C6 C7 94.80(18) . . ?
C5 C6 C7 142.7(3) . . ?
C6 C7 H7 116.3 . . ?
C6 C7 C8 85.62(16) . . ?
C8 C7 H7 116.3 . . ?
C16 C7 C6 113.74(17) . . ?
C16 C7 H7 116.3 . . ?
C16 C7 C8 104.09(16) . . ?
N1 C8 C1 113.99(16) . . ?
N1 C8 C7 103.25(15) . . ?
N1 C8 C9 112.11(15) . . ?
C1 C8 C7 85.89(16) . . ?
C9 C8 C1 118.32(17) . . ?
C9 C8 C7 120.19(16) . . ?
C10 C9 C8 119.40(19) . . ?
C10 C9 C14 118.84(19) . . ?
C14 C9 C8 121.74(18) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.5(2) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.8(2) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.6(2) . . ?
C14 C13 H13 119.2 . . ?
C9 C14 C15 122.80(19) . . ?
C13 C14 C9 118.4(2) . . ?
C13 C14 C15 118.8(2) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C7 130.2(2) . . ?
C17 C16 C21 120.1(2) . . ?
C21 C16 C7 109.61(18) . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.7(2) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(2) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.2 . . ?
C18 C19 C20 121.6(2) . . ?
C20 C19 H19 119.2 . . ?
C19 C20 H20 120.9 . . ?
C21 C20 C19 118.2(2) . . ?
C21 C20 H20 120.9 . . ?
N1 C21 C16 111.58(17) . . ?
C20 C21 N1 127.72(19) . . ?
C20 C21 C16 120.56(19) . . ?
C23 C22 N1 120.91(18) . . ?
C27 C22 N1 120.02(19) . . ?
C27 C22 C23 119.04(19) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.5(2) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.6(2) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 H26 119.7 . . ?
C25 C26 C27 120.7(2) . . ?
C27 C26 H26 119.7 . . ?
C22 C27 C26 120.0(2) . . ?
C22 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2071528'
loop_
_audit_author_name
_audit_author_address
'Xinyu Chen'
;Huaibei Normal University
China
;
_audit_update_record             
;
2021-03-19 deposited with the CCDC.	2021-06-15 downloaded from the CCDC.
;
_audit_creation_date             2021-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 N'
_chemical_formula_sum            'C20 H15 N'
_chemical_formula_weight         269.33
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   18.566(2)
_cell_length_b                   5.4612(7)
_cell_length_c                   14.391(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1459.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1605
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0705 before and 0.0328 after correction.
The Ratio of minimum to maximum transmission is 0.8423.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6897
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.583
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                1786
_reflns_number_total             2555
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 618 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2555
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0366P)²+0.0253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0915
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 N1, C20
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 N1, C7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17), C18(H18), C19(H19), C0AA(H0AA)
;
_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
C2 C 0.8760(2) 0.3860(8) 0.5199(3) 0.0649(11) Uani 1 1 d . . . . .
H2 H 0.8836 0.2533 0.4806 0.078 Uiso 1 1 calc R . . . .
C3 C 0.8115(2) 0.5073(8) 0.5187(3) 0.0700(13) Uani 1 1 d . . . . .
H3 H 0.7752 0.4561 0.4786 0.084 Uiso 1 1 calc R . . . .
C4 C 0.8001(2) 0.7033(8) 0.5760(3) 0.0649(12) Uani 1 1 d . . . . .
H4 H 0.7568 0.7885 0.5735 0.078 Uiso 1 1 calc R . . . .
C5 C 0.85305(19) 0.7740(7) 0.6373(3) 0.0530(11) Uani 1 1 d . . . . .
H5 H 0.8445 0.9036 0.6777 0.064 Uiso 1 1 calc R . . . .
C6 C 0.91872(19) 0.6550(7) 0.6397(2) 0.0416(9) Uani 1 1 d . . . . .
C7 C 0.97688(16) 0.7350(6) 0.7043(2) 0.0394(8) Uani 1 1 d . U . . .
C8 C 0.95580(17) 0.7976(6) 0.8010(2) 0.0399(9) Uani 1 1 d . . . . .
C9 C 0.90692(17) 0.6475(7) 0.8475(2) 0.0477(10) Uani 1 1 d . . . . .
H9 H 0.8872 0.5133 0.8169 0.057 Uiso 1 1 calc R . . . .
C10 C 0.8873(2) 0.6952(8) 0.9381(3) 0.0599(11) Uani 1 1 d . . . . .
H10 H 0.8555 0.5917 0.9690 0.072 Uiso 1 1 calc R . . . .
C11 C 0.9150(2) 0.8953(9) 0.9822(3) 0.0654(12) Uani 1 1 d . . . . .
H11 H 0.9010 0.9298 1.0429 0.078 Uiso 1 1 calc R . . . .
C12 C 0.9631(2) 1.0461(7) 0.9386(3) 0.0595(11) Uani 1 1 d . . . . .
H12 H 0.9816 1.1811 0.9699 0.071 Uiso 1 1 calc R . . . .
C13 C 0.98480(18) 0.9989(6) 0.8472(2) 0.0472(9) Uani 1 1 d . . . . .
C14 C 1.0401(2) 1.1522(6) 0.7986(3) 0.0597(11) Uani 1 1 d . . . . .
H14A H 1.0520 1.2937 0.8364 0.072 Uiso 1 1 calc R . . . .
H14B H 1.0211 1.2098 0.7398 0.072 Uiso 1 1 calc R . . . .
C15 C 1.1068(2) 1.0013(7) 0.7821(3) 0.0480(10) Uani 1 1 d . . . . .
C16 C 1.1719(2) 1.0537(7) 0.8247(3) 0.0613(11) Uani 1 1 d . . . . .
H16 H 1.1751 1.1886 0.8640 0.074 Uiso 1 1 calc R . . . .
C17 C 1.2319(2) 0.9110(9) 0.8104(3) 0.0679(12) Uani 1 1 d . . . . .
H17 H 1.2749 0.9488 0.8404 0.082 Uiso 1 1 calc R . . . .
C18 C 1.2285(2) 0.7134(8) 0.7520(3) 0.0668(12) Uani 1 1 d . . . . .
H18 H 1.2690 0.6165 0.7424 0.080 Uiso 1 1 calc R . . . .
C19 C 1.16481(19) 0.6590(7) 0.7078(3) 0.0564(11) Uani 1 1 d . . . . .
H19 H 1.1630 0.5275 0.6668 0.068 Uiso 1 1 calc R . . . .
C20 C 1.10312(18) 0.7974(6) 0.7233(2) 0.0420(8) Uani 1 1 d . U . . .
C0AA C 0.9298(2) 0.4612(7) 0.5795(3) 0.0533(10) Uani 1 1 d . . . . .
H0AA H 0.9740 0.3808 0.5792 0.064 Uiso 1 1 calc R . . . .
N1 N 1.04145(14) 0.7313(5) 0.67185(19) 0.0430(7) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 H2 0.9300 . ?
C2 C3 1.370(5) . ?
C2 C0AA 1.379(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(5) . ?
C6 C7 1.490(5) . ?
C6 C0AA 1.384(5) . ?
C7 C8 1.486(5) . ?
C7 N1 1.287(4) . ?
C8 C9 1.394(4) . ?
C8 C13 1.392(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.380(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.365(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.368(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.399(5) . ?
C13 C14 1.499(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.506(5) . ?
C15 C16 1.385(5) . ?
C15 C20 1.400(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.368(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.390(5) . ?
C20 N1 1.410(4) . ?
C0AA H0AA 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 H2 120.1 . . ?
C3 C2 C0AA 119.8(4) . . ?
C0AA C2 H2 120.1 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(4) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.7(4) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(4) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 121.2(3) . . ?
C5 C6 C0AA 118.4(3) . . ?
C0AA C6 C7 120.5(3) . . ?
C8 C7 C6 117.4(3) . . ?
N1 C7 C6 116.4(3) . . ?
N1 C7 C8 126.1(3) . . ?
C9 C8 C7 119.0(3) . . ?
C13 C8 C7 121.8(3) . . ?
C13 C8 C9 119.2(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(4) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.4(4) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.0(4) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.6(4) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 118.9(3) . . ?
C8 C13 C14 118.9(3) . . ?
C12 C13 C14 122.2(3) . . ?
C13 C14 H14A 109.8 . . ?
C13 C14 H14B 109.8 . . ?
C13 C14 C15 109.4(3) . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 H14A 109.8 . . ?
C15 C14 H14B 109.8 . . ?
C16 C15 C14 122.2(4) . . ?
C16 C15 C20 118.4(4) . . ?
C20 C15 C14 119.4(3) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.5(4) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.1(4) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.6(4) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.1(4) . . ?
C20 C19 H19 119.4 . . ?
C15 C20 N1 124.1(3) . . ?
C19 C20 C15 119.3(3) . . ?
C19 C20 N1 116.5(3) . . ?
C2 C0AA C6 120.6(3) . . ?
C2 C0AA H0AA 119.7 . . ?
C6 C0AA H0AA 119.7 . . ?
C7 N1 C20 124.2(3) . . ?

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 C5 -2.1(6) . . . . ?
C3 C2 C0AA C6 1.4(6) . . . . ?
C3 C4 C5 C6 2.3(6) . . . . ?
C4 C5 C6 C7 178.4(3) . . . . ?
C4 C5 C6 C0AA -0.6(5) . . . . ?
C5 C6 C7 C8 43.0(4) . . . . ?
C5 C6 C7 N1 -140.4(3) . . . . ?
C5 C6 C0AA C2 -1.2(6) . . . . ?
C6 C7 C8 C9 42.8(4) . . . . ?
C6 C7 C8 C13 -138.7(3) . . . . ?
C6 C7 N1 C20 -179.1(3) . . . . ?
C7 C6 C0AA C2 179.8(3) . . . . ?
C7 C8 C9 C10 178.3(3) . . . . ?
C7 C8 C13 C12 -179.4(3) . . . . ?
C7 C8 C13 C14 -1.6(5) . . . . ?
C8 C7 N1 C20 -2.8(5) . . . . ?
C8 C9 C10 C11 1.5(5) . . . . ?
C8 C13 C14 C15 -64.9(4) . . . . ?
C9 C8 C13 C12 -0.9(5) . . . . ?
C9 C8 C13 C14 176.9(3) . . . . ?
C9 C10 C11 C12 -1.5(6) . . . . ?
C10 C11 C12 C13 0.3(6) . . . . ?
C11 C12 C13 C8 0.9(5) . . . . ?
C11 C12 C13 C14 -176.9(3) . . . . ?
C12 C13 C14 C15 112.8(4) . . . . ?
C13 C8 C9 C10 -0.3(5) . . . . ?
C13 C14 C15 C16 -114.4(4) . . . . ?
C13 C14 C15 C20 64.1(4) . . . . ?
C14 C15 C16 C17 178.6(4) . . . . ?
C14 C15 C20 C19 179.7(3) . . . . ?
C14 C15 C20 N1 4.9(5) . . . . ?
C15 C16 C17 C18 0.7(6) . . . . ?
C15 C20 N1 C7 -43.0(5) . . . . ?
C16 C15 C20 C19 -1.7(5) . . . . ?
C16 C15 C20 N1 -176.5(3) . . . . ?
C16 C17 C18 C19 0.1(6) . . . . ?
C17 C18 C19 C20 -1.8(6) . . . . ?
C18 C19 C20 C15 2.6(6) . . . . ?
C18 C19 C20 N1 177.8(3) . . . . ?
C19 C20 N1 C7 142.1(3) . . . . ?
C20 C15 C16 C17 0.0(5) . . . . ?
C0AA C2 C3 C4 0.3(6) . . . . ?
C0AA C6 C7 C8 -138.0(3) . . . . ?
C0AA C6 C7 N1 38.6(5) . . . . ?
N1 C7 C8 C9 -133.4(3) . . . . ?
N1 C7 C8 C13 45.1(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
