# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_aaaa
_database_code_depnum_ccdc_archive 'CCDC 2102093'
loop_
_audit_author_name
_audit_author_address
'Dong-Liang Mo'
;Guangxi Normal University
China
;
_audit_update_record             
;
2021-08-08 deposited with the CCDC.	2021-10-20 downloaded from the CCDC.
;
_audit_creation_date             2019-06-30
_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         'C22 H18 N2'
_chemical_formula_sum            'C22 H18 N2'
_chemical_formula_weight         310.38
_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      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                   9.87(4)
_cell_length_b                   20.34(8)
_cell_length_c                   8.95(4)
_cell_angle_alpha                90.00(7)
_cell_angle_beta                 108.57(7)
_cell_angle_gamma                90.00(8)
_cell_volume                     1703(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1441
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.0305
_cell_measurement_theta_min      2.1945
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1044
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12723
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.808
_diffrn_reflns_theta_min         2.002
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2335
_reflns_number_total             3490
_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 v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3490
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0701
_refine_ls_restrained_S_all      1.012
_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)+(0.1340P)²+0.1584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1870
_refine_ls_wR_factor_ref         0.2176
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.4912(2) 0.26808(9) 0.4226(2) 0.0455(5) Uani 1 1 d . . . . .
H1 H 0.5002 0.3079 0.4564 0.055 Uiso 1 1 d R . . . .
N2 N 0.58901(19) 0.13354(9) 0.22192(19) 0.0431(5) Uani 1 1 d . . . . .
C1 C 0.3917(2) 0.22325(11) 0.4379(2) 0.0423(5) Uani 1 1 d . . . . .
C2 C 0.2844(3) 0.23052(11) 0.5062(3) 0.0493(6) Uani 1 1 d . . . . .
H2 H 0.2749 0.2693 0.5572 0.059 Uiso 1 1 calc R . . . .
C3 C 0.1925(3) 0.17847(12) 0.4960(3) 0.0542(6) Uani 1 1 d . . . . .
H3 H 0.1200 0.1828 0.5410 0.065 Uiso 1 1 calc R . . . .
C4 C 0.2038(2) 0.11896(12) 0.4203(3) 0.0518(6) Uani 1 1 d . . . . .
C5 C 0.3132(2) 0.11208(11) 0.3569(2) 0.0462(6) Uani 1 1 d . . . . .
H5 H 0.3232 0.0729 0.3079 0.055 Uiso 1 1 calc R . . . .
C6 C 0.4100(2) 0.16389(10) 0.3658(2) 0.0406(5) Uani 1 1 d . . . . .
C7 C 0.0965(3) 0.06416(15) 0.4081(4) 0.0753(8) Uani 1 1 d . . . . .
H7A H 0.0990 0.0510 0.5119 0.113 Uiso 1 1 calc GR . . . .
H7B H 0.1203 0.0273 0.3542 0.113 Uiso 1 1 calc GR . . . .
H7C H 0.0024 0.0795 0.3504 0.113 Uiso 1 1 calc GR . . . .
C8 C 0.5280(2) 0.17522(10) 0.3072(2) 0.0411(5) Uani 1 1 d . . . . .
C9 C 0.5734(2) 0.23897(11) 0.3427(2) 0.0433(5) Uani 1 1 d . . . . .
C10 C 0.6797(2) 0.27732(11) 0.2965(2) 0.0439(5) Uani 1 1 d . . . . .
C11 C 0.8089(3) 0.24951(14) 0.2940(3) 0.0611(7) Uani 1 1 d . . . . .
H11 H 0.8314 0.2065 0.3280 0.073 Uiso 1 1 calc R . . . .
C12 C 0.9026(3) 0.28561(17) 0.2415(4) 0.0747(8) Uani 1 1 d . . . . .
H12 H 0.9876 0.2667 0.2389 0.090 Uiso 1 1 calc R . . . .
C13 C 0.8710(3) 0.34990(16) 0.1928(3) 0.0715(8) Uani 1 1 d . . . . .
H13 H 0.9355 0.3743 0.1592 0.086 Uiso 1 1 calc R . . . .
C14 C 0.7447(3) 0.37780(13) 0.1937(3) 0.0645(7) Uani 1 1 d . . . . .
H14 H 0.7228 0.4208 0.1590 0.077 Uiso 1 1 calc R . . . .
C15 C 0.6501(3) 0.34186(12) 0.2463(3) 0.0527(6) Uani 1 1 d . . . . .
H15 H 0.5653 0.3612 0.2482 0.063 Uiso 1 1 calc R . . . .
C16 C 0.5934(2) 0.07200(11) 0.2449(2) 0.0470(6) Uani 1 1 d . . . . .
H16 H 0.5494 0.0553 0.3145 0.056 Uiso 1 1 calc R . . . .
C17 C 0.6634(2) 0.02566(11) 0.1685(2) 0.0446(5) Uani 1 1 d . . . . .
C18 C 0.7366(3) 0.04732(12) 0.0688(3) 0.0563(6) Uani 1 1 d . . . . .
H18 H 0.7382 0.0918 0.0449 0.068 Uiso 1 1 calc R . . . .
C19 C 0.8070(3) 0.00218(14) 0.0059(3) 0.0695(8) Uani 1 1 d . . . . .
H19 H 0.8551 0.0166 -0.0621 0.083 Uiso 1 1 calc R . . . .
C20 C 0.8081(3) -0.06339(15) 0.0407(3) 0.0719(8) Uani 1 1 d . . . . .
H20 H 0.8577 -0.0928 -0.0022 0.086 Uiso 1 1 calc R . . . .
C21 C 0.7366(3) -0.08542(13) 0.1381(3) 0.0710(8) Uani 1 1 d . . . . .
H21 H 0.7363 -0.1299 0.1616 0.085 Uiso 1 1 calc R . . . .
C22 C 0.6649(3) -0.04108(12) 0.2013(3) 0.0597(7) Uani 1 1 d . . . . .
H22 H 0.6161 -0.0562 0.2679 0.072 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 H1 0.8585 . ?
N1 C1 1.379(5) . ?
N1 C9 1.375(4) . ?
N2 C8 1.398(4) . ?
N2 C16 1.267(6) . ?
C1 C2 1.389(5) . ?
C1 C6 1.407(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.409(6) . ?
C4 C5 1.378(5) . ?
C4 C7 1.517(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.407(5) . ?
C6 C8 1.441(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.376(6) . ?
C9 C10 1.468(5) . ?
C10 C11 1.402(6) . ?
C10 C15 1.388(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.461(5) . ?
C17 C18 1.387(5) . ?
C17 C22 1.388(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.369(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.360(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.375(5) . ?
C22 H22 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
C1 N1 H1 125.8 . . ?
C9 N1 H1 125.3 . . ?
C9 N1 C1 108.9(3) . . ?
C16 N2 C8 120.6(3) . . ?
N1 C1 C2 129.8(3) . . ?
N1 C1 C6 108.8(3) . . ?
C2 C1 C6 121.3(2) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.8(3) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 H3 118.6 . . ?
C2 C3 C4 122.7(3) . . ?
C4 C3 H3 118.6 . . ?
C3 C4 C7 120.4(3) . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 C7 121.1(3) . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C8 105.4(2) . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 C8 135.4(2) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C6 129.8(3) . . ?
C9 C8 N2 122.2(3) . . ?
C9 C8 C6 107.9(2) . . ?
N1 C9 C8 108.9(3) . . ?
N1 C9 C10 120.7(3) . . ?
C8 C9 C10 130.1(2) . . ?
C11 C10 C9 121.7(3) . . ?
C15 C10 C9 119.9(3) . . ?
C15 C10 C11 118.4(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.3(4) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.8(4) . . ?
C15 C14 H14 120.1 . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 121.0(3) . . ?
C14 C15 H15 119.5 . . ?
N2 C16 H16 118.0 . . ?
N2 C16 C17 123.9(3) . . ?
C17 C16 H16 118.0 . . ?
C18 C17 C16 121.2(3) . . ?
C18 C17 C22 118.3(2) . . ?
C22 C17 C16 120.4(3) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 C17 119.1(3) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 H19 119.2 . . ?
C20 C19 C18 121.7(3) . . ?
C20 C19 H19 119.2 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.2(3) . . ?
C22 C21 H21 120.4 . . ?
C17 C22 H22 119.1 . . ?
C21 C22 C17 121.8(3) . . ?
C21 C22 H22 119.1 . . ?

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 C1 C2 C3 175.7(2) . . . . ?
N1 C1 C6 C5 -175.54(18) . . . . ?
N1 C1 C6 C8 0.6(2) . . . . ?
N1 C9 C10 C11 145.7(3) . . . . ?
N1 C9 C10 C15 -37.5(3) . . . . ?
N2 C8 C9 N1 178.20(18) . . . . ?
N2 C8 C9 C10 4.2(3) . . . . ?
N2 C16 C17 C18 3.0(3) . . . . ?
N2 C16 C17 C22 179.3(2) . . . . ?
C1 N1 C9 C8 -0.4(2) . . . . ?
C1 N1 C9 C10 174.27(19) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C1 C6 C8 N2 -178.0(2) . . . . ?
C1 C6 C8 C9 -0.9(2) . . . . ?
C2 C1 C6 C5 2.9(3) . . . . ?
C2 C1 C6 C8 179.06(19) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C2 C3 C4 C7 -178.0(2) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C4 C5 C6 C8 -175.9(2) . . . . ?
C5 C6 C8 N2 -2.8(4) . . . . ?
C5 C6 C8 C9 174.3(2) . . . . ?
C6 C1 C2 C3 -2.4(3) . . . . ?
C6 C8 C9 N1 0.8(2) . . . . ?
C6 C8 C9 C10 -173.2(2) . . . . ?
C7 C4 C5 C6 178.5(2) . . . . ?
C8 N2 C16 C17 -175.8(2) . . . . ?
C8 C9 C10 C11 -40.9(4) . . . . ?
C8 C9 C10 C15 135.9(3) . . . . ?
C9 N1 C1 C2 -178.4(2) . . . . ?
C9 N1 C1 C6 -0.1(2) . . . . ?
C9 C10 C11 C12 176.3(2) . . . . ?
C9 C10 C15 C14 -176.3(2) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C11 C10 C15 C14 0.6(3) . . . . ?
C11 C12 C13 C14 -1.2(4) . . . . ?
C12 C13 C14 C15 1.2(4) . . . . ?
C13 C14 C15 C10 -0.9(4) . . . . ?
C15 C10 C11 C12 -0.6(4) . . . . ?
C16 N2 C8 C6 -33.2(3) . . . . ?
C16 N2 C8 C9 150.0(2) . . . . ?
C16 C17 C18 C19 176.7(2) . . . . ?
C16 C17 C22 C21 -176.3(2) . . . . ?
C17 C18 C19 C20 -0.9(4) . . . . ?
C18 C17 C22 C21 0.1(4) . . . . ?
C18 C19 C20 C21 0.9(4) . . . . ?
C19 C20 C21 C22 -0.5(4) . . . . ?
C20 C21 C22 C17 0.0(4) . . . . ?
C22 C17 C18 C19 0.3(4) . . . . ?

_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_20180605_mdl_cwl_6_57
_database_code_depnum_ccdc_archive 'CCDC 2102094'
loop_
_audit_author_name
_audit_author_address
'Dong-Liang Mo'
;Guangxi Normal University
China
;
_audit_update_record             
;
2021-08-08 deposited with the CCDC.	2021-10-20 downloaded from the CCDC.
;
_audit_creation_date             2019-06-30
_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         'C20 H14 N2'
_chemical_formula_sum            'C20 H14 N2'
_chemical_formula_weight         282.33
_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 0.0033 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      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                   7.9106(3)
_cell_length_b                   10.4113(4)
_cell_length_c                   18.0346(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.689(4)
_cell_angle_gamma                90
_cell_volume                     1468.28(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2378
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.9170
_cell_measurement_theta_min      3.7360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_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  0.0398
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10925
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.616
_diffrn_reflns_theta_min         3.258
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6296
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -78.00   99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6002    0.0000  -90.0000 177

#__ type_ start__ end____ width___ exp.time_
  2 omega  -99.00  -34.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.9283  178.0000  -90.0000 65

#__ type_ start__ end____ width___ exp.time_
  3 omega  -20.00    5.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.9283  -99.0000  150.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0261615000
_diffrn_orient_matrix_UB_12      -0.0144516000
_diffrn_orient_matrix_UB_13      -0.0349776000
_diffrn_orient_matrix_UB_21      0.0384559000
_diffrn_orient_matrix_UB_22      0.0615028000
_diffrn_orient_matrix_UB_23      -0.0003596000
_diffrn_orient_matrix_UB_31      0.0778750000
_diffrn_orient_matrix_UB_32      -0.0255255000
_diffrn_orient_matrix_UB_33      0.0189474000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2003
_reflns_number_total             3576
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1247
_refine_ls_R_factor_gt           0.0639
_refine_ls_restrained_S_all      1.034
_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)+(0.0476P)²+0.3851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1526
_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:
 C20(H20), C10(H10), C4(H4), C18(H18), C2(H2), C3(H3), C5(H5), C11(H11),
 C19(H19), C16(H16), C14(H14), C17(H17), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.7708(2) 0.52243(16) 0.04443(10) 0.0482(5) Uani 1 1 d . . . . .
N2 N 0.4644(2) 0.42326(16) 0.15554(10) 0.0487(5) Uani 1 1 d . . . . .
C7 C 0.5725(2) 0.42585(18) 0.10961(11) 0.0389(5) Uani 1 1 d . . . . .
C8 C 0.6747(2) 0.54472(18) 0.09504(11) 0.0408(5) Uani 1 1 d . . . . .
C1 C 0.7443(2) 0.39263(19) 0.02047(12) 0.0441(5) Uani 1 1 d . . . . .
C9 C 0.6712(2) 0.67199(18) 0.13015(12) 0.0425(5) Uani 1 1 d . . . . .
C15 C 0.3704(3) 0.30896(19) 0.16398(12) 0.0447(5) Uani 1 1 d . . . . .
C6 C 0.6291(2) 0.32836(18) 0.05890(11) 0.0403(5) Uani 1 1 d . . . . .
C20 C 0.4190(3) 0.2300(2) 0.22475(13) 0.0553(6) Uani 1 1 d . . . . .
H20 H 0.5149 0.2502 0.2593 0.066 Uiso 1 1 calc R . . . .
C10 C 0.7559(3) 0.7737(2) 0.10126(13) 0.0500(6) Uani 1 1 d . . . . .
H10 H 0.8134 0.7595 0.0607 0.060 Uiso 1 1 calc R . . . .
C4 C 0.6687(3) 0.1412(2) -0.01230(13) 0.0560(6) Uani 1 1 d . . . . .
H4 H 0.6446 0.0554 -0.0237 0.067 Uiso 1 1 calc R . . . .
C18 C 0.1839(3) 0.0907(2) 0.18388(14) 0.0581(6) Uani 1 1 d . . . . .
H18 H 0.1232 0.0158 0.1897 0.070 Uiso 1 1 calc R . . . .
C2 C 0.8205(3) 0.3341(2) -0.03389(13) 0.0574(6) Uani 1 1 d . . . . .
H2 H 0.8972 0.3782 -0.0589 0.069 Uiso 1 1 calc R . . . .
C3 C 0.7796(3) 0.2066(2) -0.05040(13) 0.0593(6) Uani 1 1 d . . . . .
H3 H 0.8279 0.1649 -0.0877 0.071 Uiso 1 1 calc R . . . .
C5 C 0.5918(3) 0.2009(2) 0.04289(13) 0.0507(6) Uani 1 1 d . . . . .
H5 H 0.5168 0.1560 0.0685 0.061 Uiso 1 1 calc R . . . .
C11 C 0.7557(3) 0.8940(2) 0.13178(14) 0.0587(6) Uani 1 1 d . . . . .
H11 H 0.8125 0.9608 0.1117 0.070 Uiso 1 1 calc R . . . .
C19 C 0.3255(3) 0.1213(2) 0.23438(14) 0.0594(6) Uani 1 1 d . . . . .
H19 H 0.3588 0.0682 0.2755 0.071 Uiso 1 1 calc R . . . .
C16 C 0.2249(3) 0.2808(2) 0.11438(13) 0.0603(6) Uani 1 1 d . . . . .
H16 H 0.1892 0.3352 0.0741 0.072 Uiso 1 1 calc R . . . .
C14 C 0.5879(3) 0.6961(2) 0.19069(14) 0.0588(6) Uani 1 1 d . . . . .
H14 H 0.5308 0.6298 0.2110 0.071 Uiso 1 1 calc R . . . .
C17 C 0.1323(3) 0.1713(2) 0.12471(14) 0.0662(7) Uani 1 1 d . . . . .
H17 H 0.0342 0.1522 0.0912 0.079 Uiso 1 1 calc R . . . .
C12 C 0.6720(3) 0.9167(2) 0.19203(16) 0.0664(7) Uani 1 1 d . . . . .
H12 H 0.6718 0.9986 0.2127 0.080 Uiso 1 1 calc R . . . .
C13 C 0.5886(3) 0.8177(2) 0.22138(16) 0.0720(7) Uani 1 1 d . . . . .
H13 H 0.5321 0.8326 0.2622 0.086 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 1.294(2) . ?
N1 C1 1.425(3) . ?
N2 C7 1.278(2) . ?
N2 C15 1.423(2) . ?
C7 C8 1.523(3) . ?
C7 C6 1.480(3) . ?
C8 C9 1.471(3) . ?
C1 C6 1.396(3) . ?
C1 C2 1.370(3) . ?
C9 C10 1.396(3) . ?
C9 C14 1.381(3) . ?
C15 C20 1.377(3) . ?
C15 C16 1.379(3) . ?
C6 C5 1.381(3) . ?
C20 C19 1.377(3) . ?
C10 C11 1.368(3) . ?
C4 C3 1.374(3) . ?
C4 C5 1.389(3) . ?
C18 C19 1.371(3) . ?
C18 C17 1.370(3) . ?
C2 C3 1.388(3) . ?
C11 C12 1.376(3) . ?
C16 C17 1.383(3) . ?
C14 C13 1.382(3) . ?
C12 C13 1.373(3) . ?

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
C8 N1 C1 107.97(16) . . ?
C7 N2 C15 119.89(17) . . ?
N2 C7 C8 123.64(18) . . ?
N2 C7 C6 132.89(17) . . ?
C6 C7 C8 103.46(16) . . ?
N1 C8 C7 111.10(17) . . ?
N1 C8 C9 121.09(18) . . ?
C9 C8 C7 127.80(18) . . ?
C6 C1 N1 112.42(18) . . ?
C2 C1 N1 125.36(18) . . ?
C2 C1 C6 122.21(19) . . ?
C10 C9 C8 118.79(19) . . ?
C14 C9 C8 123.11(18) . . ?
C14 C9 C10 118.09(19) . . ?
C20 C15 N2 119.77(18) . . ?
C20 C15 C16 119.65(19) . . ?
C16 C15 N2 120.46(19) . . ?
C1 C6 C7 105.02(16) . . ?
C5 C6 C7 135.51(19) . . ?
C5 C6 C1 119.46(19) . . ?
C15 C20 C19 120.0(2) . . ?
C11 C10 C9 121.0(2) . . ?
C3 C4 C5 121.2(2) . . ?
C17 C18 C19 119.5(2) . . ?
C1 C2 C3 117.7(2) . . ?
C4 C3 C2 120.8(2) . . ?
C6 C5 C4 118.5(2) . . ?
C10 C11 C12 120.3(2) . . ?
C18 C19 C20 120.5(2) . . ?
C15 C16 C17 119.7(2) . . ?
C9 C14 C13 120.6(2) . . ?
C18 C17 C16 120.6(2) . . ?
C13 C12 C11 119.5(2) . . ?
C12 C13 C14 120.5(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
