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

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

data_hm1804_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2220977'
loop_
_audit_author_name
_audit_author_address
'Shantanu Nandi'
;CSIR Indian Institute of Chemical Biology
India
;
_audit_update_record             
;
2022-11-21 deposited with the CCDC.	2023-04-13 downloaded from the CCDC.
;
_audit_creation_date             2022-05-11
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        triclinic
_chemical_formula_moiety         'C18 H14 N2'
_chemical_formula_sum            'C18 H14 N2'
_chemical_formula_weight         258.31
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.5843(3)
_cell_length_b                   9.6121(4)
_cell_length_c                   20.5866(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.7440(10)
_cell_angle_gamma                90
_cell_volume                     1300.12(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      72.22
_cell_measurement_theta_min      4.30
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.914
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0940 before and 0.0683 after correction.
The Ratio of minimum to maximum transmission is 0.8251.
The λ/2 correction factor is Not present.
;
_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    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23131
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.223
_diffrn_reflns_theta_min         4.304
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX III 8D venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2395
_reflns_number_total             2472
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2472
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.064
_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)+(0.0611P)²+0.3876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1125
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C5(H5), C00A(H00A), C6(H6), C7(H7), C11(H11), C4(H4),
 C14(H14), C00I(H00I), C15(H15), C16(H16)
;
_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
N2 N 0.16802(15) 0.51075(10) 0.56624(5) 0.0249(3) Uani 1 1 d . . . . .
N1 N 0.43631(15) 0.64048(10) 0.54189(4) 0.0241(2) Uani 1 1 d . . . . .
C1 C 0.32830(17) 0.48872(11) 0.61216(5) 0.0213(3) Uani 1 1 d . . . . .
C9 C 0.33556(17) 0.40306(11) 0.66874(5) 0.0212(3) Uani 1 1 d . . . . .
C2 C 0.49660(17) 0.56754(11) 0.59767(5) 0.0215(3) Uani 1 1 d . . . . .
C10 C 0.52048(17) 0.40377(11) 0.70864(5) 0.0213(3) Uani 1 1 d . . . . .
C3 C 0.68260(17) 0.56560(12) 0.63586(5) 0.0229(3) Uani 1 1 d . . . . .
H3 H 0.796859 0.618024 0.624085 0.027 Uiso 1 1 calc R U . . .
C8 C 0.16927(17) 0.32259(12) 0.68716(6) 0.0243(3) Uani 1 1 d . . . . .
H8 H 0.046210 0.321437 0.660367 0.029 Uiso 1 1 calc R U . . .
C5 C 0.53133(18) 0.32262(12) 0.76613(6) 0.0246(3) Uani 1 1 d . . . . .
H5 H 0.653880 0.321117 0.793166 0.029 Uiso 1 1 calc R U . . .
C00A C 0.47525(18) 0.92131(12) 0.59718(6) 0.0257(3) Uani 1 1 d . . . . .
H00A H 0.343017 0.882040 0.597934 0.031 Uiso 1 1 calc R U . . .
C13 C 0.61360(18) 0.86646(12) 0.55554(5) 0.0236(3) Uani 1 1 d . . . . .
C6 C 0.36749(19) 0.24613(12) 0.78335(6) 0.0275(3) Uani 1 1 d . . . . .
H6 H 0.377209 0.192864 0.822295 0.033 Uiso 1 1 calc R U . . .
C7 C 0.18448(18) 0.24597(12) 0.74361(6) 0.0278(3) Uani 1 1 d . . . . .
H7 H 0.071609 0.192785 0.755917 0.033 Uiso 1 1 calc R U . . .
C11 C 0.23985(18) 0.60184(12) 0.52583(6) 0.0257(3) Uani 1 1 d . . . . .
H11 H 0.162296 0.637333 0.488966 0.031 Uiso 1 1 calc R U . . .
C4 C 0.69057(17) 0.48485(12) 0.69051(5) 0.0227(3) Uani 1 1 d . . . . .
H4 H 0.813193 0.482286 0.717491 0.027 Uiso 1 1 calc R U . . .
C12 C 0.55661(19) 0.74599(12) 0.51056(6) 0.0273(3) Uani 1 1 d . . . . .
H12A H 0.477650 0.781669 0.471496 0.033 Uiso 1 1 calc R U . . .
H12B H 0.682300 0.702553 0.496096 0.033 Uiso 1 1 calc R U . . .
C14 C 0.80674(19) 0.92529(12) 0.55531(6) 0.0270(3) Uani 1 1 d . . . . .
H14 H 0.902707 0.888590 0.527354 0.032 Uiso 1 1 calc R U . . .
C00I C 0.72214(19) 1.09117(12) 0.63677(6) 0.0280(3) Uani 1 1 d . . . . .
H00I H 0.758832 1.167634 0.664326 0.034 Uiso 1 1 calc R U . . .
C15 C 0.86066(19) 1.03738(13) 0.59567(6) 0.0294(3) Uani 1 1 d . . . . .
H15 H 0.992687 1.076998 0.594989 0.035 Uiso 1 1 calc R U . . .
C16 C 0.52921(19) 1.03287(13) 0.63757(6) 0.0277(3) Uani 1 1 d . . . . .
H16 H 0.433959 1.069428 0.665809 0.033 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
N2 C1 1.3864(15) . ?
N2 C11 1.3166(16) . ?
N1 C2 1.3814(15) . ?
N1 C11 1.3655(15) . ?
N1 C12 1.4624(15) . ?
C1 C9 1.4246(16) . ?
C1 C2 1.3907(16) . ?
C9 C10 1.4236(16) . ?
C9 C8 1.4125(16) . ?
C2 C3 1.4116(16) . ?
C10 C5 1.4153(16) . ?
C10 C4 1.4337(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3649(16) . ?
C8 H8 0.9500 . ?
C8 C7 1.3739(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3711(17) . ?
C00A H00A 0.9500 . ?
C00A C13 1.3946(16) . ?
C00A C16 1.3888(17) . ?
C13 C12 1.5145(16) . ?
C13 C14 1.3920(17) . ?
C6 H6 0.9500 . ?
C6 C7 1.4116(18) . ?
C7 H7 0.9500 . ?
C11 H11 0.9500 . ?
C4 H4 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 H14 0.9500 . ?
C14 C15 1.3923(17) . ?
C00I H00I 0.9500 . ?
C00I C15 1.3842(17) . ?
C00I C16 1.3895(18) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N2 C1 104.10(10) . . ?
C2 N1 C12 125.74(10) . . ?
C11 N1 C2 106.23(10) . . ?
C11 N1 C12 127.85(10) . . ?
N2 C1 C9 128.99(10) . . ?
N2 C1 C2 110.63(10) . . ?
C2 C1 C9 120.36(10) . . ?
C10 C9 C1 116.80(10) . . ?
C8 C9 C1 123.42(11) . . ?
C8 C9 C10 119.76(10) . . ?
N1 C2 C1 105.37(10) . . ?
N1 C2 C3 131.41(10) . . ?
C1 C2 C3 123.22(10) . . ?
C9 C10 C4 120.36(10) . . ?
C5 C10 C9 118.32(10) . . ?
C5 C10 C4 121.31(10) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 C2 116.86(10) . . ?
C4 C3 H3 121.6 . . ?
C9 C8 H8 119.8 . . ?
C7 C8 C9 120.38(11) . . ?
C7 C8 H8 119.8 . . ?
C10 C5 H5 119.5 . . ?
C6 C5 C10 120.94(11) . . ?
C6 C5 H5 119.5 . . ?
C13 C00A H00A 119.7 . . ?
C16 C00A H00A 119.7 . . ?
C16 C00A C13 120.53(11) . . ?
C00A C13 C12 121.28(11) . . ?
C14 C13 C00A 118.82(11) . . ?
C14 C13 C12 119.90(10) . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.47(11) . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.13(11) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
N2 C11 N1 113.68(10) . . ?
N2 C11 H11 123.2 . . ?
N1 C11 H11 123.2 . . ?
C10 C4 H4 118.8 . . ?
C3 C4 C10 122.35(11) . . ?
C3 C4 H4 118.8 . . ?
N1 C12 C13 112.36(9) . . ?
N1 C12 H12A 109.1 . . ?
N1 C12 H12B 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.65(11) . . ?
C15 C14 H14 119.7 . . ?
C15 C00I H00I 120.1 . . ?
C15 C00I C16 119.73(11) . . ?
C16 C00I H00I 120.1 . . ?
C14 C15 H15 120.0 . . ?
C00I C15 C14 120.09(11) . . ?
C00I C15 H15 120.0 . . ?
C00A C16 C00I 120.18(11) . . ?
C00A C16 H16 119.9 . . ?
C00I C16 H16 119.9 . . ?

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 C9 C10 -178.06(10) . . . . ?
N2 C1 C9 C8 0.25(18) . . . . ?
N2 C1 C2 N1 0.64(12) . . . . ?
N2 C1 C2 C3 -179.67(10) . . . . ?
N1 C2 C3 C4 177.41(11) . . . . ?
C1 N2 C11 N1 0.31(13) . . . . ?
C1 C9 C10 C5 178.42(9) . . . . ?
C1 C9 C10 C4 -1.69(15) . . . . ?
C1 C9 C8 C7 -177.73(10) . . . . ?
C1 C2 C3 C4 -2.18(16) . . . . ?
C9 C1 C2 N1 -178.03(9) . . . . ?
C9 C1 C2 C3 1.65(17) . . . . ?
C9 C10 C5 C6 -0.57(16) . . . . ?
C9 C10 C4 C3 1.17(16) . . . . ?
C9 C8 C7 C6 -0.60(17) . . . . ?
C2 N1 C11 N2 0.08(13) . . . . ?
C2 N1 C12 C13 -58.83(15) . . . . ?
C2 C1 C9 C10 0.34(15) . . . . ?
C2 C1 C9 C8 178.65(10) . . . . ?
C2 C3 C4 C10 0.75(16) . . . . ?
C10 C9 C8 C7 0.53(16) . . . . ?
C10 C5 C6 C7 0.51(17) . . . . ?
C8 C9 C10 C5 0.05(15) . . . . ?
C8 C9 C10 C4 179.93(10) . . . . ?
C5 C10 C4 C3 -178.94(10) . . . . ?
C5 C6 C7 C8 0.08(18) . . . . ?
C00A C13 C12 N1 -40.53(15) . . . . ?
C00A C13 C14 C15 -0.35(17) . . . . ?
C13 C00A C16 C00I 0.08(18) . . . . ?
C13 C14 C15 C00I 0.28(18) . . . . ?
C11 N2 C1 C9 177.94(11) . . . . ?
C11 N2 C1 C2 -0.59(12) . . . . ?
C11 N1 C2 C1 -0.43(12) . . . . ?
C11 N1 C2 C3 179.92(11) . . . . ?
C11 N1 C12 C13 115.61(12) . . . . ?
C4 C10 C5 C6 179.55(10) . . . . ?
C12 N1 C2 C1 175.00(10) . . . . ?
C12 N1 C2 C3 -4.65(19) . . . . ?
C12 N1 C11 N2 -175.22(10) . . . . ?
C12 C13 C14 C15 179.07(11) . . . . ?
C14 C13 C12 N1 140.07(11) . . . . ?
C15 C00I C16 C00A -0.16(18) . . . . ?
C16 C00A C13 C12 -179.24(10) . . . . ?
C16 C00A C13 C14 0.17(17) . . . . ?
C16 C00I C15 C14 -0.02(18) . . . . ?

_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_f
_database_code_depnum_ccdc_archive 'CCDC 2220979'
loop_
_audit_author_name
_audit_author_address
'Shantanu Nandi'
;CSIR Indian Institute of Chemical Biology
India
;
_audit_update_record             
;
2022-11-21 deposited with the CCDC.	2023-04-13 downloaded from the CCDC.
;
_audit_creation_date             2022-05-11
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        monoclinic
_chemical_formula_moiety         'C17 H18 N2'
_chemical_formula_sum            'C17 H18 N2'
_chemical_formula_weight         250.33
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.2417(9)
_cell_length_b                   12.7619(9)
_cell_length_c                   7.8090(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.428(3)
_cell_angle_gamma                90
_cell_volume                     1301.81(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      72.48
_cell_measurement_theta_min      3.46
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.918
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1735 before and 0.1122 after correction.
The Ratio of minimum to maximum transmission is 0.4340.
The λ/2 correction factor is Not present.
;
_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    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            25331
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.480
_diffrn_reflns_theta_min         4.844
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-III 8D VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2356
_reflns_number_total             2532
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.062(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2532
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0672
_refine_ls_restrained_S_all      1.071
_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)+(0.1260P)²+0.3059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1766
_refine_ls_wR_factor_ref         0.1802
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C15(H15A,H15B), C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C11(H11), C8(H8), C4(H4), C7(H7), C6(H6), C5(H5)
;
_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 0.45845(10) 0.55020(10) 0.27388(16) 0.0255(4) Uani 1 1 d . . . . .
N2 N 0.59135(10) 0.45676(10) 0.20955(16) 0.0276(4) Uani 1 1 d . . . . .
C2 C 0.54604(12) 0.60451(12) 0.34301(18) 0.0249(4) Uani 1 1 d . . . . .
C1 C 0.62703(12) 0.54629(11) 0.30016(18) 0.0245(4) Uani 1 1 d . . . . .
C3 C 0.56131(13) 0.69782(12) 0.44223(19) 0.0277(4) Uani 1 1 d . . . . .
H3 H 0.505376 0.735373 0.474454 0.033 Uiso 1 1 calc R U . . .
C9 C 0.72980(12) 0.58109(12) 0.34720(18) 0.0247(4) Uani 1 1 d . . . . .
C10 C 0.74551(13) 0.67639(12) 0.44230(19) 0.0277(4) Uani 1 1 d . . . . .
C11 C 0.49123(13) 0.46340(12) 0.1986(2) 0.0283(4) Uani 1 1 d . . . . .
H11 H 0.445708 0.411759 0.142573 0.034 Uiso 1 1 calc R U . . .
C12 C 0.35170(12) 0.58292(12) 0.27555(19) 0.0260(4) Uani 1 1 d . . . . .
H12 H 0.343407 0.596303 0.398658 0.031 Uiso 1 1 calc R U . . .
C17 C 0.32644(13) 0.68450(12) 0.1721(2) 0.0273(4) Uani 1 1 d . . . . .
H17A H 0.374828 0.740322 0.220115 0.033 Uiso 1 1 calc R U . . .
H17B H 0.333984 0.673011 0.049411 0.033 Uiso 1 1 calc R U . . .
C8 C 0.81419(13) 0.52677(13) 0.30173(19) 0.0281(4) Uani 1 1 d . . . . .
H8 H 0.803677 0.462941 0.238719 0.034 Uiso 1 1 calc R U . . .
C4 C 0.65993(13) 0.73153(12) 0.48963(19) 0.0293(4) Uani 1 1 d . . . . .
H4 H 0.672169 0.793813 0.556421 0.035 Uiso 1 1 calc R U . . .
C15 C 0.13899(13) 0.63326(13) 0.1186(2) 0.0314(4) Uani 1 1 d . . . . .
H15A H 0.136139 0.622820 -0.007751 0.038 Uiso 1 1 calc R U . . .
H15B H 0.070263 0.655640 0.138429 0.038 Uiso 1 1 calc R U . . .
C13 C 0.27735(13) 0.49693(12) 0.2035(2) 0.0290(4) Uani 1 1 d . . . . .
H13A H 0.294018 0.431760 0.270940 0.035 Uiso 1 1 calc R U . . .
H13B H 0.284083 0.482639 0.081233 0.035 Uiso 1 1 calc R U . . .
C7 C 0.91156(13) 0.56560(14) 0.3480(2) 0.0329(4) Uani 1 1 d . . . . .
H7 H 0.968005 0.528835 0.316020 0.040 Uiso 1 1 calc R U . . .
C14 C 0.16720(13) 0.52982(14) 0.2131(2) 0.0335(4) Uani 1 1 d . . . . .
H14A H 0.119679 0.474339 0.160793 0.040 Uiso 1 1 calc R U . . .
H14B H 0.159132 0.537290 0.336369 0.040 Uiso 1 1 calc R U . . .
C16 C 0.21665(13) 0.71882(13) 0.1816(2) 0.0300(4) Uani 1 1 d . . . . .
H16A H 0.211485 0.737099 0.303053 0.036 Uiso 1 1 calc R U . . .
H16B H 0.200194 0.782341 0.109645 0.036 Uiso 1 1 calc R U . . .
C6 C 0.92814(14) 0.65964(15) 0.4427(2) 0.0366(5) Uani 1 1 d . . . . .
H6 H 0.995738 0.685945 0.474341 0.044 Uiso 1 1 calc R U . . .
C5 C 0.84728(14) 0.71355(14) 0.4897(2) 0.0336(4) Uani 1 1 d . . . . .
H5 H 0.859559 0.776509 0.554667 0.040 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.383(2) . ?
N1 C11 1.358(2) . ?
N1 C12 1.4760(19) . ?
N2 C1 1.3856(19) . ?
N2 C11 1.317(2) . ?
C2 C1 1.390(2) . ?
C2 C3 1.417(2) . ?
C1 C9 1.421(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.367(2) . ?
C9 C10 1.422(2) . ?
C9 C8 1.409(2) . ?
C10 C4 1.433(2) . ?
C10 C5 1.419(2) . ?
C11 H11 0.9500 . ?
C12 H12 1.0000 . ?
C12 C17 1.535(2) . ?
C12 C13 1.519(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C16 1.532(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.373(2) . ?
C4 H4 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.529(2) . ?
C15 C16 1.525(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.531(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.408(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C5 1.372(3) . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C12 126.72(12) . . ?
C11 N1 C2 105.71(13) . . ?
C11 N1 C12 127.51(14) . . ?
C11 N2 C1 103.63(13) . . ?
N1 C2 C1 105.60(13) . . ?
N1 C2 C3 132.08(14) . . ?
C1 C2 C3 122.29(15) . . ?
N2 C1 C2 110.60(14) . . ?
N2 C1 C9 128.43(14) . . ?
C2 C1 C9 120.97(14) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 C2 117.18(14) . . ?
C4 C3 H3 121.4 . . ?
C1 C9 C10 117.00(14) . . ?
C8 C9 C1 123.12(14) . . ?
C8 C9 C10 119.87(15) . . ?
C9 C10 C4 120.02(15) . . ?
C5 C10 C9 118.24(15) . . ?
C5 C10 C4 121.73(15) . . ?
N1 C11 H11 122.8 . . ?
N2 C11 N1 114.45(14) . . ?
N2 C11 H11 122.8 . . ?
N1 C12 H12 108.2 . . ?
N1 C12 C17 111.14(12) . . ?
N1 C12 C13 110.84(12) . . ?
C17 C12 H12 108.2 . . ?
C13 C12 H12 108.2 . . ?
C13 C12 C17 110.04(13) . . ?
C12 C17 H17A 109.7 . . ?
C12 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C16 C17 C12 110.03(13) . . ?
C16 C17 H17A 109.7 . . ?
C16 C17 H17B 109.7 . . ?
C9 C8 H8 119.8 . . ?
C7 C8 C9 120.34(15) . . ?
C7 C8 H8 119.8 . . ?
C3 C4 C10 122.44(14) . . ?
C3 C4 H4 118.8 . . ?
C10 C4 H4 118.8 . . ?
H15A C15 H15B 108.0 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C16 C15 C14 111.34(14) . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C12 C13 C14 110.39(13) . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
C8 C7 H7 119.8 . . ?
C8 C7 C6 120.32(16) . . ?
C6 C7 H7 119.8 . . ?
C15 C14 C13 111.84(13) . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C15 C16 C17 112.01(13) . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C7 C6 H6 119.8 . . ?
C5 C6 C7 120.43(16) . . ?
C5 C6 H6 119.8 . . ?
C10 C5 H5 119.6 . . ?
C6 C5 C10 120.79(16) . . ?
C6 C5 H5 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
N1 C2 C1 N2 -1.16(16) . . . . ?
N1 C2 C1 C9 178.24(12) . . . . ?
N1 C2 C3 C4 -179.41(14) . . . . ?
N1 C12 C17 C16 -177.90(12) . . . . ?
N1 C12 C13 C14 177.54(12) . . . . ?
N2 C1 C9 C10 -179.51(13) . . . . ?
N2 C1 C9 C8 1.5(2) . . . . ?
C2 N1 C11 N2 -1.00(18) . . . . ?
C2 N1 C12 C17 63.21(18) . . . . ?
C2 N1 C12 C13 -174.08(13) . . . . ?
C2 C1 C9 C10 1.2(2) . . . . ?
C2 C1 C9 C8 -177.79(13) . . . . ?
C2 C3 C4 C10 0.1(2) . . . . ?
C1 N2 C11 N1 0.28(17) . . . . ?
C1 C2 C3 C4 2.5(2) . . . . ?
C1 C9 C10 C4 1.3(2) . . . . ?
C1 C9 C10 C5 -179.44(13) . . . . ?
C1 C9 C8 C7 178.66(13) . . . . ?
C3 C2 C1 N2 177.37(13) . . . . ?
C3 C2 C1 C9 -3.2(2) . . . . ?
C9 C10 C4 C3 -2.0(2) . . . . ?
C9 C10 C5 C6 0.9(2) . . . . ?
C9 C8 C7 C6 0.6(2) . . . . ?
C10 C9 C8 C7 -0.3(2) . . . . ?
C11 N1 C2 C1 1.25(15) . . . . ?
C11 N1 C2 C3 -177.07(15) . . . . ?
C11 N1 C12 C17 -113.80(16) . . . . ?
C11 N1 C12 C13 8.9(2) . . . . ?
C11 N2 C1 C2 0.57(16) . . . . ?
C11 N2 C1 C9 -178.78(15) . . . . ?
C12 N1 C2 C1 -176.28(13) . . . . ?
C12 N1 C2 C3 5.4(2) . . . . ?
C12 N1 C11 N2 176.51(13) . . . . ?
C12 C17 C16 C15 -56.10(16) . . . . ?
C12 C13 C14 C15 56.36(18) . . . . ?
C17 C12 C13 C14 -59.12(16) . . . . ?
C8 C9 C10 C4 -179.64(13) . . . . ?
C8 C9 C10 C5 -0.4(2) . . . . ?
C8 C7 C6 C5 -0.1(2) . . . . ?
C4 C10 C5 C6 -179.87(14) . . . . ?
C13 C12 C17 C16 58.94(16) . . . . ?
C7 C6 C5 C10 -0.7(3) . . . . ?
C14 C15 C16 C17 53.10(17) . . . . ?
C16 C15 C14 C13 -52.98(18) . . . . ?
C5 C10 C4 C3 178.75(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
