# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_exp_183
_database_code_depnum_ccdc_archive 'CCDC 1904512'
loop_
_audit_author_name
_audit_author_address
'Guangxi Huang'
;Shenzhen University
China
;
_audit_update_record             
;
2019-03-20 deposited with the CCDC.	2020-11-10 downloaded from the CCDC.
;
_audit_creation_date             2018-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H19 N'
_chemical_formula_sum            'C27 H19 N'
_chemical_formula_weight         357.43
_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 0.0181 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'

_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      trigonal
_space_group_IT_number           144
_space_group_name_H-M_alt        'P 31'
_space_group_name_Hall           'P 31'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   9.1128(3)
_cell_length_b                   9.1128(3)
_cell_length_c                   21.2477(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1528.08(11)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    2732
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.2230
_cell_measurement_theta_min      5.5610
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.927
_exptl_absorpt_coefficient_mu    0.513
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.04374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4680
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.036
_diffrn_reflns_theta_min         4.161
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00 -14.00   0.50    0.50    --    0.00 -38.00  30.00   82
  2  ω      7.00  87.00   0.50    0.50    --    0.00  38.00  90.00  160
  3  ω      7.00 112.00   0.50    1.83    --   95.20 -45.00 120.00  210
  4  ω     79.00 152.00   0.50    1.83    --   95.20  30.00 -90.00  146
  5  ω    108.00 168.00   0.50    1.83    --   95.20  45.00 -60.00  120
  6  ω     48.00 109.00   0.50    1.83    --   95.20 -61.00 120.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1844399000
_diffrn_orient_matrix_UB_12      -0.0365430000
_diffrn_orient_matrix_UB_13      0.0013798000
_diffrn_orient_matrix_UB_21      -0.0228933000
_diffrn_orient_matrix_UB_22      -0.0586315000
_diffrn_orient_matrix_UB_23      -0.0690448000
_diffrn_orient_matrix_UB_31      -0.0602112000
_diffrn_orient_matrix_UB_32      -0.1826202000
_diffrn_orient_matrix_UB_33      0.0218617000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.897
_reflns_number_gt                2542
_reflns_number_total             2721
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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         0.194
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 675 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.2(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2721
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.037
_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)+(0.0630P)²+0.1020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1117
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.540(4)
 0.460(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C004(H004), C006(H006), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C),
 C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q)
;
_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
C001 C 0.5500(6) 0.6408(6) 0.41356(19) 0.0453(10) Uani 1 1 d . . . . .
C002 C 0.5903(6) 0.7420(6) 0.35366(19) 0.0487(11) Uani 1 1 d . . . . .
C003 C 0.4595(6) 0.4504(6) 0.40305(19) 0.0458(10) Uani 1 1 d . . . . .
C004 C 0.6306(7) 0.9749(7) 0.5217(2) 0.0562(12) Uani 1 1 d . . . . .
H004 H 0.5285 0.9094 0.5427 0.067 Uiso 1 1 calc R . . . .
C005 C 0.6884(6) 0.8977(6) 0.4809(2) 0.0473(10) Uani 1 1 d . . . . .
C006 C 0.3259(6) 0.3759(6) 0.3615(2) 0.0516(11) Uani 1 1 d . . . . .
H006 H 0.2908 0.4425 0.3405 0.062 Uiso 1 1 calc R . . . .
C007 C 0.5321(6) 0.6100(6) 0.52990(18) 0.0437(9) Uani 1 1 d . . . . .
C008 C 0.5889(6) 0.7109(6) 0.47084(19) 0.0448(10) Uani 1 1 d . . . . .
C009 C 0.6707(8) 0.7116(8) 0.3055(2) 0.0676(15) Uani 1 1 d . . . . .
H009 H 0.7048 0.6315 0.3096 0.081 Uiso 1 1 calc R . . . .
C00A C 0.8743(9) 1.2460(7) 0.5045(2) 0.0774(19) Uani 1 1 d . . . . .
H00A H 0.9364 1.3619 0.5121 0.093 Uiso 1 1 calc R . . . .
C00B C 0.8465(7) 0.9972(7) 0.4533(3) 0.0616(14) Uani 1 1 d . . . . .
H00B H 0.8922 0.9481 0.4274 0.074 Uiso 1 1 calc R . . . .
C00C C 0.3625(7) 0.4976(8) 0.5421(2) 0.0545(12) Uani 1 1 d . . . . .
H00C H 0.2810 0.4757 0.5115 0.065 Uiso 1 1 calc R . . . .
C00D C 0.5150(8) 0.3501(7) 0.4325(2) 0.0605(14) Uani 1 1 d . . . . .
H00D H 0.6083 0.4000 0.4591 0.073 Uiso 1 1 calc R . . . .
C00E C 0.4337(6) 0.4428(7) 0.64469(19) 0.0543(11) Uani 1 1 d . . . . .
C00F C 0.7212(9) 1.1481(7) 0.5323(2) 0.0656(15) Uani 1 1 d . . . . .
H00F H 0.6769 1.1978 0.5586 0.079 Uiso 1 1 calc R . . . .
C00G C 0.6491(7) 0.6369(7) 0.5762(2) 0.0547(12) Uani 1 1 d . . . . .
H00G H 0.7628 0.7143 0.5688 0.066 Uiso 1 1 calc R . . . .
C00H C 0.2431(8) 0.2027(7) 0.3509(3) 0.0670(15) Uani 1 1 d . . . . .
H00H H 0.1529 0.1523 0.3228 0.080 Uiso 1 1 calc R . . . .
C00I C 0.5363(8) 0.8600(7) 0.3455(2) 0.0604(14) Uani 1 1 d . . . . .
H00I H 0.4791 0.8780 0.3781 0.072 Uiso 1 1 calc R . . . .
C00J C 0.3150(7) 0.4179(8) 0.6005(2) 0.0656(14) Uani 1 1 d . . . . .
H00J H 0.2008 0.3466 0.6094 0.079 Uiso 1 1 calc R . . . .
C00K C 0.4341(11) 0.1807(9) 0.4225(3) 0.0804(19) Uani 1 1 d . . . . .
H00K H 0.4720 0.1153 0.4428 0.096 Uiso 1 1 calc R . . . .
C00L C 0.9354(8) 1.1699(8) 0.4648(3) 0.0758(18) Uani 1 1 d . . . . .
H00L H 1.0393 1.2362 0.4450 0.091 Uiso 1 1 calc R . . . .
C00M C 0.6448(9) 0.9186(9) 0.2430(3) 0.083(2) Uani 1 1 d . . . . .
H00M H 0.6609 0.9767 0.2053 0.099 Uiso 1 1 calc R . . . .
C00N C 0.7014(9) 0.8069(10) 0.2480(3) 0.083(2) Uani 1 1 d . . . . .
H00N H 0.7592 0.7920 0.2148 0.099 Uiso 1 1 calc R . . . .
C00O C 0.5652(9) 0.9487(9) 0.2913(3) 0.0783(17) Uani 1 1 d . . . . .
H00O H 0.5312 1.0289 0.2872 0.094 Uiso 1 1 calc R . . . .
C00P C 0.6036(7) 0.5538(7) 0.6325(2) 0.0564(13) Uani 1 1 d . . . . .
H00P H 0.6856 0.5713 0.6623 0.068 Uiso 1 1 calc R . . . .
C00Q C 0.2983(9) 0.1050(6) 0.3833(3) 0.0691(16) Uani 1 1 d . . . . .
H00Q H 0.2418 -0.0119 0.3780 0.083 Uiso 1 1 calc R . . . .
N00R N 0.3402(7) 0.2984(8) 0.75414(18) 0.0920(16) Uani 1 1 d . . . . .
C00S C 0.3833(7) 0.3647(7) 0.7057(2) 0.0659(13) 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
C001 C002 1.505(6) . ?
C001 C003 1.519(7) . ?
C001 C008 1.337(4) . ?
C002 C009 1.365(7) . ?
C002 C00I 1.399(8) . ?
C003 C006 1.376(7) . ?
C003 C00D 1.394(7) . ?
C004 H004 0.9300 . ?
C004 C005 1.377(7) . ?
C004 C00F 1.385(8) . ?
C005 C008 1.490(7) . ?
C005 C00B 1.391(7) . ?
C006 H006 0.9300 . ?
C006 C00H 1.386(7) . ?
C007 C008 1.488(6) . ?
C007 C00C 1.386(7) . ?
C007 C00G 1.379(6) . ?
C009 H009 0.9300 . ?
C009 C00N 1.444(9) . ?
C00A H00A 0.9300 . ?
C00A C00F 1.359(9) . ?
C00A C00L 1.374(10) . ?
C00B H00B 0.9300 . ?
C00B C00L 1.384(8) . ?
C00C H00C 0.9300 . ?
C00C C00J 1.392(7) . ?
C00D H00D 0.9300 . ?
C00D C00K 1.354(9) . ?
C00E C00J 1.363(7) . ?
C00E C00P 1.386(7) . ?
C00E C00S 1.438(6) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00P 1.365(7) . ?
C00H H00H 0.9300 . ?
C00H C00Q 1.403(9) . ?
C00I H00I 0.9300 . ?
C00I C00O 1.355(7) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00K C00Q 1.359(10) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00N 1.356(10) . ?
C00M C00O 1.362(10) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
N00R C00S 1.159(5) . ?

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
C002 C001 C003 113.7(4) . . ?
C008 C001 C002 123.5(4) . . ?
C008 C001 C003 122.8(3) . . ?
C009 C002 C001 120.1(5) . . ?
C009 C002 C00I 119.6(5) . . ?
C00I C002 C001 120.2(4) . . ?
C006 C003 C001 119.9(4) . . ?
C006 C003 C00D 119.0(4) . . ?
C00D C003 C001 121.0(4) . . ?
C005 C004 H004 119.3 . . ?
C005 C004 C00F 121.4(5) . . ?
C00F C004 H004 119.3 . . ?
C004 C005 C008 120.3(4) . . ?
C004 C005 C00B 117.9(5) . . ?
C00B C005 C008 121.6(4) . . ?
C003 C006 H006 119.6 . . ?
C003 C006 C00H 120.7(5) . . ?
C00H C006 H006 119.6 . . ?
C00C C007 C008 122.0(4) . . ?
C00G C007 C008 119.5(4) . . ?
C00G C007 C00C 118.4(4) . . ?
C001 C008 C005 122.7(3) . . ?
C001 C008 C007 123.0(3) . . ?
C007 C008 C005 114.2(4) . . ?
C002 C009 H009 120.8 . . ?
C002 C009 C00N 118.3(6) . . ?
C00N C009 H009 120.8 . . ?
C00F C00A H00A 120.7 . . ?
C00F C00A C00L 118.5(5) . . ?
C00L C00A H00A 120.7 . . ?
C005 C00B H00B 120.2 . . ?
C00L C00B C005 119.6(5) . . ?
C00L C00B H00B 120.2 . . ?
C007 C00C H00C 120.2 . . ?
C007 C00C C00J 119.5(5) . . ?
C00J C00C H00C 120.2 . . ?
C003 C00D H00D 119.7 . . ?
C00K C00D C003 120.6(6) . . ?
C00K C00D H00D 119.7 . . ?
C00J C00E C00P 119.8(4) . . ?
C00J C00E C00S 120.5(5) . . ?
C00P C00E C00S 119.6(4) . . ?
C004 C00F H00F 119.7 . . ?
C00A C00F C004 120.6(5) . . ?
C00A C00F H00F 119.7 . . ?
C007 C00G H00G 118.9 . . ?
C00P C00G C007 122.2(5) . . ?
C00P C00G H00G 118.9 . . ?
C006 C00H H00H 120.7 . . ?
C006 C00H C00Q 118.5(5) . . ?
C00Q C00H H00H 120.7 . . ?
C002 C00I H00I 119.1 . . ?
C00O C00I C002 121.7(6) . . ?
C00O C00I H00I 119.1 . . ?
C00C C00J H00J 119.6 . . ?
C00E C00J C00C 120.9(5) . . ?
C00E C00J H00J 119.6 . . ?
C00D C00K H00K 119.6 . . ?
C00D C00K C00Q 120.8(6) . . ?
C00Q C00K H00K 119.6 . . ?
C00A C00L C00B 121.8(6) . . ?
C00A C00L H00L 119.1 . . ?
C00B C00L H00L 119.1 . . ?
C00N C00M H00M 118.9 . . ?
C00N C00M C00O 122.2(5) . . ?
C00O C00M H00M 118.9 . . ?
C009 C00N H00N 120.5 . . ?
C00M C00N C009 119.1(6) . . ?
C00M C00N H00N 120.5 . . ?
C00I C00O C00M 119.0(6) . . ?
C00I C00O H00O 120.5 . . ?
C00M C00O H00O 120.5 . . ?
C00E C00P H00P 120.4 . . ?
C00G C00P C00E 119.2(4) . . ?
C00G C00P H00P 120.4 . . ?
C00H C00Q H00Q 119.9 . . ?
C00K C00Q C00H 120.3(5) . . ?
C00K C00Q H00Q 119.9 . . ?
N00R C00S C00E 178.5(6) . . ?

_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 19.131
_oxdiff_exptl_absorpt_empirical_full_min 0.417
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.540(4)
2 0.460(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_m-29
_database_code_depnum_ccdc_archive 'CCDC 1904513'
loop_
_audit_author_name
_audit_author_address
'Guangxi Huang'
;Shenzhen University
China
;
_audit_update_record             
;
2019-03-20 deposited with the CCDC.	2020-11-10 downloaded from the CCDC.
;
_audit_creation_date             2018-07-04
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H19 N'
_chemical_formula_sum            'C27 H19 N'
_chemical_formula_weight         357.43
_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 0.0180 0.0090 '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 0.0310 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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.5183(7)
_cell_length_b                   9.3996(6)
_cell_length_c                   10.5184(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.09
_cell_angle_gamma                90
_cell_volume                     1023.85(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1360
_cell_measurement_temperature    288(4)
_cell_measurement_theta_max      71.2010
_cell_measurement_theta_min      6.5420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.510
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.870
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3016
_diffrn_reflns_point_group_measured_fraction_full 0.562
_diffrn_reflns_point_group_measured_fraction_max 0.531
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.050
_diffrn_reflns_theta_min         4.269
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      288(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.870
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00   0.00   0.50    2.37    --    0.00 -82.00-180.00   54
  2  ω     -5.00  62.00   0.50    2.37    --    0.00  38.00 -60.00  134
  3  ω     73.00 101.00   0.50    9.47    --   95.20 -30.00  60.00   56
  4  ω     55.00 118.00   0.50    9.47    --   95.20 -15.00 -90.00  126
  5  ω     73.00 106.00   0.50    9.47    --   95.20  61.00-150.00   66
  6  ω    125.00 184.00   0.50    9.47    --   95.20  61.00-150.00  118
  7  ω     73.00 119.00   0.50    9.47    --   95.20 -61.00 -30.00   92
  8  ω     19.00  56.00   0.50    9.47    --   95.20 -61.00 -30.00   74
  9  ω      6.00  50.00   0.50    9.47    --   95.20 -15.00 -90.00   88
 10  ω     16.00  48.00   0.50    9.47    --   95.20 -30.00  60.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0721187000
_diffrn_orient_matrix_UB_12      0.0031598000
_diffrn_orient_matrix_UB_13      0.1267894000
_diffrn_orient_matrix_UB_21      0.0677756000
_diffrn_orient_matrix_UB_22      0.0631920000
_diffrn_orient_matrix_UB_23      0.0751038000
_diffrn_orient_matrix_UB_31      -0.0566831000
_diffrn_orient_matrix_UB_32      0.0715913000
_diffrn_orient_matrix_UB_33      -0.0716587000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.200
_reflns_Friedel_fraction_full    0.210
_reflns_Friedel_fraction_max     0.190
_reflns_number_gt                1471
_reflns_number_total             2210
_reflns_odcompleteness_completeness 99.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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    ?
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 
;
 Flack x determined using 217 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -6.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2210
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1264
_refine_ls_R_factor_gt           0.1131
_refine_ls_restrained_S_all      1.092
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2803
_refine_ls_wR_factor_ref         0.2970
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
  C25(H25), C26(H26), C27(H27)
;
_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
N1 N -0.7730(11) -0.4171(17) -0.7336(13) 0.180(5) Uani 1 1 d . . . . .
C1 C -0.6800(11) -0.4706(13) -0.6842(10) 0.131(3) Uani 1 1 d . . . . .
C2 C -0.5609(8) -0.5272(9) -0.6230(8) 0.105(2) Uani 1 1 d . . . . .
C3 C -0.5228(8) -0.5093(8) -0.4913(7) 0.0911(18) Uani 1 1 d . . . . .
H3 H -0.5762 -0.4609 -0.4442 0.109 Uiso 1 1 calc R . . . .
C4 C -0.4076(7) -0.5620(7) -0.4302(6) 0.0881(17) Uani 1 1 d . . . . .
C5 C -0.3319(9) -0.6384(8) -0.5027(8) 0.099(2) Uani 1 1 d . . . . .
H5 H -0.2535 -0.6762 -0.4623 0.118 Uiso 1 1 calc R . . . .
C6 C -0.3704(13) -0.6583(11) -0.6300(10) 0.125(3) Uani 1 1 d . . . . .
H6 H -0.3178 -0.7099 -0.6757 0.150 Uiso 1 1 calc R . . . .
C7 C -0.4843(11) -0.6052(10) -0.6941(9) 0.118(3) Uani 1 1 d . . . . .
H7 H -0.5102 -0.6202 -0.7822 0.142 Uiso 1 1 calc R . . . .
C8 C -0.3663(7) -0.5420(6) -0.2870(6) 0.0852(17) Uani 1 1 d . . . . .
C9 C -0.2451(7) -0.5022(6) -0.2333(6) 0.0825(16) Uani 1 1 d . . . . .
C10 C -0.1934(7) -0.5145(8) -0.0970(7) 0.0886(17) Uani 1 1 d . . . . .
C11 C -0.2098(8) -0.6381(9) -0.0300(8) 0.102(2) Uani 1 1 d . . . . .
H11 H -0.2591 -0.7124 -0.0711 0.122 Uiso 1 1 calc R . . . .
C12 C -0.1527(9) -0.6502(14) 0.0981(9) 0.125(3) Uani 1 1 d . . . . .
H12 H -0.1624 -0.7346 0.1415 0.149 Uiso 1 1 calc R . . . .
C13 C -0.0835(10) -0.5443(18) 0.1621(9) 0.132(4) Uani 1 1 d . . . . .
H13 H -0.0482 -0.5548 0.2490 0.158 Uiso 1 1 calc R . . . .
C14 C -0.0652(9) -0.4207(15) 0.0988(10) 0.126(3) Uani 1 1 d . . . . .
H14 H -0.0161 -0.3476 0.1422 0.151 Uiso 1 1 calc R . . . .
C15 C -0.1211(8) -0.4046(10) -0.0323(8) 0.107(2) Uani 1 1 d . . . . .
H15 H -0.1095 -0.3205 -0.0755 0.129 Uiso 1 1 calc R . . . .
C16 C -0.1546(8) -0.4446(7) -0.3194(8) 0.094(2) Uani 1 1 d . . . . .
C17 C -0.0244(9) -0.4927(10) -0.2949(10) 0.113(2) Uani 1 1 d . . . . .
H17 H 0.0063 -0.5567 -0.2292 0.136 Uiso 1 1 calc R . . . .
C18 C 0.0563(13) -0.4350(17) -0.3792(18) 0.162(6) Uani 1 1 d . . . . .
H18 H 0.1417 -0.4653 -0.3670 0.194 Uiso 1 1 calc R . . . .
C19 C 0.020(3) -0.345(3) -0.470(2) 0.204(10) Uani 1 1 d . . . . .
H19 H 0.0773 -0.3143 -0.5219 0.245 Uiso 1 1 calc R . . . .
C20 C -0.109(2) -0.2931(15) -0.4902(13) 0.165(6) Uani 1 1 d . . . . .
H20 H -0.1372 -0.2270 -0.5546 0.198 Uiso 1 1 calc R . . . .
C21 C -0.1912(11) -0.3450(10) -0.4095(9) 0.120(3) Uani 1 1 d . . . . .
H21 H -0.2746 -0.3088 -0.4190 0.144 Uiso 1 1 calc R . . . .
C22 C -0.4691(6) -0.5664(7) -0.2075(6) 0.0826(16) Uani 1 1 d . . . . .
C23 C -0.5499(7) -0.6836(9) -0.2271(8) 0.0958(19) Uani 1 1 d . . . . .
H23 H -0.5380 -0.7500 -0.2895 0.115 Uiso 1 1 calc R . . . .
C24 C -0.6468(9) -0.7052(12) -0.1576(9) 0.114(3) Uani 1 1 d . . . . .
H24 H -0.6968 -0.7872 -0.1701 0.136 Uiso 1 1 calc R . . . .
C25 C -0.6693(9) -0.6070(13) -0.0710(9) 0.114(3) Uani 1 1 d . . . . .
H25 H -0.7367 -0.6200 -0.0255 0.137 Uiso 1 1 calc R . . . .
C26 C -0.5937(9) -0.4884(12) -0.0498(8) 0.110(3) Uani 1 1 d . . . . .
H26 H -0.6090 -0.4212 0.0106 0.132 Uiso 1 1 calc R . . . .
C27 C -0.4933(7) -0.4682(8) -0.1188(6) 0.0913(18) Uani 1 1 d . . . . .
H27 H -0.4423 -0.3870 -0.1044 0.110 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 C1 1.141(15) . ?
C1 C2 1.408(14) . ?
C2 C3 1.384(11) . ?
C2 C7 1.399(13) . ?
C3 H3 0.9300 . ?
C3 C4 1.362(10) . ?
C4 C5 1.394(10) . ?
C4 C8 1.504(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.342(14) . ?
C6 H6 0.9300 . ?
C6 C7 1.363(15) . ?
C7 H7 0.9300 . ?
C8 C9 1.353(10) . ?
C8 C22 1.496(10) . ?
C9 C10 1.447(10) . ?
C9 C16 1.524(10) . ?
C10 C11 1.384(11) . ?
C10 C15 1.388(11) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(13) . ?
C12 H12 0.9300 . ?
C12 C13 1.342(18) . ?
C13 H13 0.9300 . ?
C13 C14 1.369(19) . ?
C14 H14 0.9300 . ?
C14 C15 1.409(14) . ?
C15 H15 0.9300 . ?
C16 C17 1.422(12) . ?
C16 C21 1.340(12) . ?
C17 H17 0.9300 . ?
C17 C18 1.437(17) . ?
C18 H18 0.9300 . ?
C18 C19 1.28(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.42(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.403(17) . ?
C21 H21 0.9300 . ?
C22 C23 1.385(11) . ?
C22 C27 1.367(9) . ?
C23 H23 0.9300 . ?
C23 C24 1.369(12) . ?
C24 H24 0.9300 . ?
C24 C25 1.346(15) . ?
C25 H25 0.9300 . ?
C25 C26 1.364(14) . ?
C26 H26 0.9300 . ?
C26 C27 1.395(12) . ?
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
N1 C1 C2 175.9(13) . . ?
C3 C2 C1 119.3(8) . . ?
C3 C2 C7 120.4(8) . . ?
C7 C2 C1 120.2(8) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(7) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 118.4(6) . . ?
C3 C4 C8 120.2(6) . . ?
C5 C4 C8 121.3(6) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.1(9) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.1 . . ?
C5 C6 C7 121.8(9) . . ?
C7 C6 H6 119.1 . . ?
C2 C7 H7 121.1 . . ?
C6 C7 C2 117.8(8) . . ?
C6 C7 H7 121.1 . . ?
C9 C8 C4 122.6(6) . . ?
C9 C8 C22 122.0(6) . . ?
C22 C8 C4 115.5(6) . . ?
C8 C9 C10 123.7(5) . . ?
C8 C9 C16 119.4(6) . . ?
C10 C9 C16 116.8(6) . . ?
C11 C10 C9 120.8(7) . . ?
C11 C10 C15 118.8(7) . . ?
C15 C10 C9 120.3(7) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.6(9) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 118.9 . . ?
C13 C12 C11 122.2(11) . . ?
C13 C12 H12 118.9 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.7(9) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.8(10) . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 119.9(9) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C9 117.5(7) . . ?
C21 C16 C9 122.4(8) . . ?
C21 C16 C17 119.9(8) . . ?
C16 C17 H17 122.5 . . ?
C16 C17 C18 115.0(11) . . ?
C18 C17 H17 122.5 . . ?
C17 C18 H18 117.4 . . ?
C19 C18 C17 125.2(17) . . ?
C19 C18 H18 117.4 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.5(13) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 121.2 . . ?
C21 C20 C19 117.6(14) . . ?
C21 C20 H20 121.2 . . ?
C16 C21 C20 122.6(13) . . ?
C16 C21 H21 118.7 . . ?
C20 C21 H21 118.7 . . ?
C23 C22 C8 121.6(6) . . ?
C27 C22 C8 121.1(6) . . ?
C27 C22 C23 117.1(6) . . ?
C22 C23 H23 118.9 . . ?
C24 C23 C22 122.2(8) . . ?
C24 C23 H23 118.9 . . ?
C23 C24 H24 120.2 . . ?
C25 C24 C23 119.7(10) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.3(8) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.1 . . ?
C25 C26 C27 119.9(8) . . ?
C27 C26 H26 120.0 . . ?
C22 C27 C26 120.8(8) . . ?
C22 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -179.5(8) . . . . ?
C1 C2 C7 C6 -179.6(10) . . . . ?
C2 C3 C4 C5 -2.3(10) . . . . ?
C2 C3 C4 C8 179.8(7) . . . . ?
C3 C2 C7 C6 -1.9(12) . . . . ?
C3 C4 C5 C6 0.8(12) . . . . ?
C3 C4 C8 C9 -135.6(7) . . . . ?
C3 C4 C8 C22 43.3(9) . . . . ?
C4 C5 C6 C7 0.1(15) . . . . ?
C4 C8 C9 C10 -164.7(6) . . . . ?
C4 C8 C9 C16 13.6(9) . . . . ?
C4 C8 C22 C23 45.9(8) . . . . ?
C4 C8 C22 C27 -129.3(6) . . . . ?
C5 C4 C8 C9 46.5(9) . . . . ?
C5 C4 C8 C22 -134.6(7) . . . . ?
C5 C6 C7 C2 0.5(15) . . . . ?
C7 C2 C3 C4 2.9(11) . . . . ?
C8 C4 C5 C6 178.7(8) . . . . ?
C8 C9 C10 C11 46.0(10) . . . . ?
C8 C9 C10 C15 -137.0(7) . . . . ?
C8 C9 C16 C17 -137.3(7) . . . . ?
C8 C9 C16 C21 47.3(10) . . . . ?
C8 C22 C23 C24 -178.1(8) . . . . ?
C8 C22 C27 C26 176.8(7) . . . . ?
C9 C8 C22 C23 -135.2(7) . . . . ?
C9 C8 C22 C27 49.6(9) . . . . ?
C9 C10 C11 C12 176.0(7) . . . . ?
C9 C10 C15 C14 -176.6(7) . . . . ?
C9 C16 C17 C18 179.9(7) . . . . ?
C9 C16 C21 C20 -179.1(9) . . . . ?
C10 C9 C16 C17 41.1(9) . . . . ?
C10 C9 C16 C21 -134.3(8) . . . . ?
C10 C11 C12 C13 1.7(14) . . . . ?
C11 C10 C15 C14 0.5(11) . . . . ?
C11 C12 C13 C14 -1.8(15) . . . . ?
C12 C13 C14 C15 1.2(15) . . . . ?
C13 C14 C15 C10 -0.6(13) . . . . ?
C15 C10 C11 C12 -1.0(11) . . . . ?
C16 C9 C10 C11 -132.3(7) . . . . ?
C16 C9 C10 C15 44.7(9) . . . . ?
C16 C17 C18 C19 1.1(18) . . . . ?
C17 C16 C21 C20 5.6(14) . . . . ?
C17 C18 C19 C20 2(2) . . . . ?
C18 C19 C20 C21 -1(2) . . . . ?
C19 C20 C21 C16 -2.8(18) . . . . ?
C21 C16 C17 C18 -4.6(12) . . . . ?
C22 C8 C9 C10 16.4(9) . . . . ?
C22 C8 C9 C16 -165.3(6) . . . . ?
C22 C23 C24 C25 3.0(13) . . . . ?
C23 C22 C27 C26 1.4(10) . . . . ?
C23 C24 C25 C26 -1.9(14) . . . . ?
C24 C25 C26 C27 0.6(13) . . . . ?
C25 C26 C27 C22 -0.3(12) . . . . ?
C27 C22 C23 C24 -2.7(11) . . . . ?

_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 2.501
_oxdiff_exptl_absorpt_empirical_full_min 0.266
####################################################################### 
# 
# 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_cxy0756_0m
_database_code_depnum_ccdc_archive 'CCDC 1917322'
loop_
_audit_author_name
_audit_author_address
'Guangxi Huang'
;Shenzhen University
China
;
_audit_update_record             
;
2019-05-20 deposited with the CCDC.	2020-11-10 downloaded from the CCDC.
;
_audit_creation_date             2019-05-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H19 N'
_chemical_formula_sum            'C27 H19 N'
_chemical_formula_weight         357.43
_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 0.0181 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'

_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      tetragonal
_space_group_IT_number           130
_space_group_name_H-M_alt        'P 4/n c c'
_space_group_name_Hall           '-P 4a 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x, z'
'-x+1/2, -y+1/2, z'
'y, -x+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'y+1/2, x+1/2, -z+1/2'
'-y, -x, -z+1/2'
'-x, -y, -z'
'y-1/2, -x, -z'
'x-1/2, y-1/2, -z'
'-y, x-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'
'-y-1/2, -x-1/2, z-1/2'
'y, x, z-1/2'

_cell_length_a                   13.91783(16)
_cell_length_b                   13.91783(16)
_cell_length_c                   10.4029(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2015.11(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4260
_cell_measurement_temperature    130
_cell_measurement_theta_max      50.337
_cell_measurement_theta_min      6.204
_shelx_estimated_absorpt_T_max   0.827
_shelx_estimated_absorpt_T_min   0.812
_exptl_absorpt_coefficient_mu    0.519
_exptl_absorpt_correction_T_max  0.7500
_exptl_absorpt_correction_T_min  0.6628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0759 before and 0.0585 after correction. The Ratio of minimum to maximum transmission is 0.8837. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.38
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9168
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.469
_diffrn_reflns_theta_min         4.493
_diffrn_ambient_temperature      130
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                880
_reflns_number_total             1034
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.252
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1034
_refine_ls_number_restraints     101
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0593
_refine_ls_restrained_S_all      1.195
_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)+(0.1160P)²+0.1938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2031
_refine_ls_wR_factor_ref         0.2121
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained planarity
 N1, C14, C10, C11, C12, C13, C8, C9
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
4. Others
 Fixed Sof: N1(0.25) C6(0.5) C5(0.5) H5(0.5) C4(0.5) H4(0.5) C3(0.5) H3(0.5)
 C2(0.5) H2(0.5) C1(0.5) H1(0.5) C7(0.5) C8(0.5) C13(0.5) H13(0.5) C12(0.5)
 H12(0.5) C11(0.5) H11(0.5) C10(0.5) H10(0.25) C9(0.5) H9(0.5) C14(0.25)
5.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C3(H3), C2(H2), C1(H1), C13(H13), C12(H12), C11(H11),
 C10(H10), C9(H9)
5.b Fitted hexagon refined as free rotating group:
 C6(C5,C4,C3,C2,C1), C8(C13,C12,C11,C10,C9)
;
_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 0.3013(4) 0.7508(4) 0.2106(8) 0.117(3) Uani 0.25 1 d . U P A -2
C6 C 0.6955(3) 0.87857(14) 0.0424(4) 0.0625(12) Uani 0.5 1 d . U P B -1
C5 C 0.7387(2) 0.9295(2) 0.1417(4) 0.0701(11) Uani 0.5 1 d G U P B -1
H5 H 0.777265 0.896805 0.203120 0.084 Uiso 0.5 1 calc R . P B -1
C4 C 0.7256(2) 1.0282(2) 0.1512(3) 0.0841(13) Uani 0.5 1 d G U P B -1
H4 H 0.755136 1.063042 0.219112 0.101 Uiso 0.5 1 calc R . P B -1
C3 C 0.6692(3) 1.07606(14) 0.0614(4) 0.0898(15) Uani 0.5 1 d G U P B -1
H3 H 0.660190 1.143551 0.067919 0.108 Uiso 0.5 1 calc R . P B -1
C2 C 0.6259(3) 1.0251(2) -0.0379(4) 0.0921(15) Uani 0.5 1 d G U P B -1
H2 H 0.587374 1.057823 -0.099266 0.110 Uiso 0.5 1 calc R . P B -1
C1 C 0.6391(3) 0.9264(2) -0.0474(4) 0.0746(12) Uani 0.5 1 d G U P B -1
H1 H 0.609502 0.891586 -0.115260 0.090 Uiso 0.5 1 calc R . P B -1
C7 C 0.7070(2) 0.7716(3) 0.0347(2) 0.0595(7) Uani 0.5 1 d . U P . .
C8 C 0.61338(18) 0.7181(3) 0.0278(5) 0.0670(14) Uani 0.5 1 d . U P B -1
C13 C 0.6004(3) 0.6458(4) -0.0627(5) 0.0924(17) Uani 0.5 1 d G U P B -1
H13 H 0.651667 0.628357 -0.118311 0.111 Uiso 0.5 1 calc R . P B -1
C12 C 0.5125(3) 0.5989(3) -0.0717(4) 0.1100(18) Uani 0.5 1 d G U P B -1
H12 H 0.503647 0.549436 -0.133504 0.132 Uiso 0.5 1 calc R . P B -1
C11 C 0.4375(2) 0.6244(3) 0.0097(5) 0.1096(19) Uani 0.5 1 d G U P B -1
H11 H 0.377429 0.592333 0.003562 0.132 Uiso 0.5 1 calc R . P B -1
C10 C 0.4505(2) 0.6967(3) 0.1002(4) 0.0958(17) Uani 0.5 1 d G U P . .
H10 H 0.399230 0.714154 0.155821 0.115 Uiso 0.25 1 calc R . P B -1
C9 C 0.5384(2) 0.7436(2) 0.1092(4) 0.0778(13) Uani 0.5 1 d G U P B -1
H9 H 0.547248 0.793077 0.171015 0.093 Uiso 0.5 1 calc R . P B -1
C14 C 0.3691(5) 0.7259(4) 0.1600(6) 0.102(2) Uani 0.25 1 d . U P A -2


_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 C14 1.135(10) . ?
C6 C5 1.3900 . ?
C6 C1 1.3900 . ?
C6 C7 1.499(5) . ?
C5 C4 1.3900 . ?
C4 C3 1.3900 . ?
C3 C2 1.3900 . ?
C2 C1 1.3900 . ?
C7 C7 0.947(3) 4_565 ?
C7 C7 0.947(3) 2_655 ?
C7 C7 1.340(5) 3_665 ?
C7 C8 1.503(5) . ?
C8 C13 1.3900 . ?
C8 C9 1.3900 . ?
C13 C12 1.3900 . ?
C12 C11 1.3900 . ?
C11 C10 1.3900 . ?
C10 C9 1.3900 . ?
C10 C14 1.355(9) . ?

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 C6 C1 120.0 . . ?
C5 C6 C7 120.0(3) . . ?
C1 C6 C7 120.0(3) . . ?
C4 C5 C6 120.0 . . ?
C5 C4 C3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C3 C2 C1 120.0 . . ?
C2 C1 C6 120.0 . . ?
C6 C7 C8 113.7(3) . . ?
C7 C7 C6 167.5(6) 2_655 . ?
C7 C7 C6 122.8(6) 3_665 . ?
C7 C7 C6 77.9(6) 4_565 . ?
C7 C7 C7 45.0 4_565 3_665 ?
C7 C7 C7 45.001(1) 2_655 3_665 ?
C7 C7 C7 90.002(1) 4_565 2_655 ?
C7 C7 C8 123.5(6) 3_665 . ?
C7 C7 C8 168.2(5) 4_565 . ?
C7 C7 C8 78.6(6) 2_655 . ?
C13 C8 C7 120.3(3) . . ?
C13 C8 C9 120.0 . . ?
C9 C8 C7 119.7(3) . . ?
C12 C13 C8 120.0 . . ?
C13 C12 C11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C9 C10 C11 120.0 . . ?
C10 C9 C8 120.0 . . ?
N1 C14 C10 179.5(6) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
