# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

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

data_f1
_database_code_depnum_ccdc_archive 'CCDC 2202808'
loop_
_audit_author_name
_audit_author_address
'Dibyajyoti Pathak'
;Indian Institute of Science Education and Research,Bhopal
India
;
_audit_update_record             
;
2022-08-22 deposited with the CCDC.	2022-10-10 downloaded from the CCDC.
;
_audit_creation_date             2022-08-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            cDP2
_chemical_name_systematic        cycloDiazoP2
_chemical_formula_moiety         'C19 H13 N5 O2'
_chemical_formula_sum            'C19 H13 N5 O2'
_chemical_formula_weight         343.34
_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'
O O 0.0106 0.0060 '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                   7.0433(11)
_cell_length_b                   18.398(3)
_cell_length_c                   12.1141(19)
_cell_angle_alpha                90
_cell_angle_beta                 104.353(8)
_cell_angle_gamma                90
_cell_volume                     1520.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5785
_cell_measurement_temperature    140
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.813
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7110
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0489 before and 0.0364 after correction.
The Ratio of minimum to maximum transmission is 0.9539.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_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  0.0206
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10881
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.813
_diffrn_ambient_temperature      140
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2700
_reflns_number_total             3070
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3070
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.058
_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)+(0.0467P)²+0.8203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1039
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N5(H5), C16(H16), C8(H8), C11(H11), C9(H9), C17(H17), C15(H15),
 C14(H14), C10(H10), C4(H4), C2(H2A), C3(H3)
;
_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
O1 O 0.28988(16) 0.43894(6) 0.01128(8) 0.0284(3) Uani 1 1 d . . . . .
O2 O 0.55434(16) 0.69242(6) 0.45326(9) 0.0284(3) Uani 1 1 d . . . . .
N1 N 0.46426(17) 0.56498(6) 0.23080(10) 0.0193(3) Uani 1 1 d . . . . .
N3 N 0.70324(17) 0.42703(7) 0.39525(10) 0.0203(3) Uani 1 1 d . . . . .
N2 N 0.54215(18) 0.44008(7) 0.17433(10) 0.0233(3) Uani 1 1 d . . . . .
H2 H 0.629740 0.472158 0.208614 0.028 Uiso 1 1 calc R U . . .
N5 N 0.64324(17) 0.57198(7) 0.44074(10) 0.0214(3) Uani 1 1 d . . . . .
H5 H 0.626697 0.536576 0.390402 0.026 Uiso 1 1 calc R U . . .
N4 N 0.80281(17) 0.41939(7) 0.49635(10) 0.0213(3) Uani 1 1 d . . . . .
C12 C 0.67684(19) 0.36094(8) 0.32979(12) 0.0189(3) Uani 1 1 d . . . . .
C18 C 0.75723(19) 0.55384(8) 0.54820(12) 0.0197(3) Uani 1 1 d . . . . .
C7 C 0.5847(2) 0.36905(8) 0.21279(12) 0.0194(3) Uani 1 1 d . . . . .
C16 C 0.9151(2) 0.58541(9) 0.74310(12) 0.0244(3) Uani 1 1 d . . . . .
H16 H 0.943007 0.620518 0.802432 0.029 Uiso 1 1 calc R U . . .
C13 C 0.8305(2) 0.48157(8) 0.56926(12) 0.0203(3) Uani 1 1 d . . . . .
C1 C 0.4408(2) 0.62876(8) 0.27677(12) 0.0203(3) Uani 1 1 d . . . . .
C5 C 0.3627(2) 0.54806(8) 0.12629(12) 0.0198(3) Uani 1 1 d . . . . .
C8 C 0.5461(2) 0.30813(8) 0.14250(12) 0.0229(3) Uani 1 1 d . . . . .
H8 H 0.483557 0.313387 0.063879 0.027 Uiso 1 1 calc R U . . .
C11 C 0.7282(2) 0.29167(8) 0.37362(12) 0.0227(3) Uani 1 1 d . . . . .
H11 H 0.789637 0.285744 0.452270 0.027 Uiso 1 1 calc R U . . .
C19 C 0.5525(2) 0.63586(8) 0.40032(12) 0.0210(3) Uani 1 1 d . . . . .
C6 C 0.3919(2) 0.46924(8) 0.09433(12) 0.0207(3) Uani 1 1 d . . . . .
C9 C 0.5993(2) 0.23994(8) 0.18776(13) 0.0247(3) Uani 1 1 d . . . . .
H9 H 0.573669 0.198438 0.139700 0.030 Uiso 1 1 calc R U . . .
C17 C 0.8018(2) 0.60477(8) 0.63669(12) 0.0233(3) Uani 1 1 d . . . . .
H17 H 0.753758 0.653065 0.623591 0.028 Uiso 1 1 calc R U . . .
C15 C 0.9885(2) 0.51537(9) 0.76431(12) 0.0245(3) Uani 1 1 d . . . . .
H15 H 1.067177 0.502524 0.837335 0.029 Uiso 1 1 calc R U . . .
C14 C 0.9454(2) 0.46469(8) 0.67764(12) 0.0229(3) Uani 1 1 d . . . . .
H14 H 0.995570 0.416772 0.692234 0.027 Uiso 1 1 calc R U . . .
C10 C 0.6901(2) 0.23144(8) 0.30306(13) 0.0256(3) Uani 1 1 d . . . . .
H10 H 0.725913 0.184335 0.333235 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2337(2) 0.59711(9) 0.06031(12) 0.0254(3) Uani 1 1 d . . . . .
H4 H 0.160621 0.584604 -0.014218 0.030 Uiso 1 1 calc R U . . .
C2 C 0.3173(2) 0.68166(8) 0.21684(13) 0.0247(3) Uani 1 1 d . . . . .
H2A H 0.303510 0.727501 0.250111 0.030 Uiso 1 1 calc R U . . .
C3 C 0.2141(2) 0.66521(9) 0.10620(13) 0.0278(3) Uani 1 1 d . . . . .
H3 H 0.130197 0.700517 0.061875 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
O1 C6 1.2171(17) . ?
O2 C19 1.2208(18) . ?
N1 C1 1.3266(19) . ?
N1 C5 1.3277(18) . ?
N3 N4 1.2593(16) . ?
N3 C12 1.4383(18) . ?
N2 H2 0.8800 . ?
N2 C7 1.3948(19) . ?
N2 C6 1.3558(18) . ?
N5 H5 0.8800 . ?
N5 C18 1.3901(18) . ?
N5 C19 1.3692(19) . ?
N4 C13 1.4288(19) . ?
C12 C7 1.4128(19) . ?
C12 C11 1.394(2) . ?
C18 C13 1.426(2) . ?
C18 C17 1.400(2) . ?
C7 C8 1.393(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(2) . ?
C16 C15 1.389(2) . ?
C13 C14 1.396(2) . ?
C1 C19 1.514(2) . ?
C1 C2 1.385(2) . ?
C5 C6 1.528(2) . ?
C5 C4 1.385(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.385(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(2) . ?
C17 H17 0.9500 . ?
C15 H15 0.9500 . ?
C15 C14 1.381(2) . ?
C14 H14 0.9500 . ?
C10 H10 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.391(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.390(2) . ?
C3 H3 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
C1 N1 C5 120.93(12) . . ?
N4 N3 C12 113.99(12) . . ?
C7 N2 H2 113.8 . . ?
C6 N2 H2 113.8 . . ?
C6 N2 C7 132.42(13) . . ?
C18 N5 H5 114.7 . . ?
C19 N5 H5 114.7 . . ?
C19 N5 C18 130.62(12) . . ?
N3 N4 C13 118.01(12) . . ?
C7 C12 N3 115.36(12) . . ?
C11 C12 N3 125.25(13) . . ?
C11 C12 C7 119.34(13) . . ?
N5 C18 C13 119.39(12) . . ?
N5 C18 C17 121.62(13) . . ?
C17 C18 C13 118.99(13) . . ?
N2 C7 C12 116.18(12) . . ?
C8 C7 N2 123.81(13) . . ?
C8 C7 C12 119.99(13) . . ?
C17 C16 H16 119.6 . . ?
C17 C16 C15 120.90(14) . . ?
C15 C16 H16 119.6 . . ?
C18 C13 N4 130.39(13) . . ?
C14 C13 N4 111.21(13) . . ?
C14 C13 C18 118.38(13) . . ?
N1 C1 C19 113.77(12) . . ?
N1 C1 C2 121.94(13) . . ?
C2 C1 C19 124.23(13) . . ?
N1 C5 C6 112.92(12) . . ?
N1 C5 C4 121.25(14) . . ?
C4 C5 C6 125.62(13) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.66(13) . . ?
C9 C8 H8 120.2 . . ?
C12 C11 H11 119.9 . . ?
C10 C11 C12 120.30(13) . . ?
C10 C11 H11 119.9 . . ?
O2 C19 N5 126.92(13) . . ?
O2 C19 C1 121.88(13) . . ?
N5 C19 C1 111.19(12) . . ?
O1 C6 N2 127.29(14) . . ?
O1 C6 C5 123.72(13) . . ?
N2 C6 C5 108.96(12) . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.74(14) . . ?
C10 C9 H9 119.6 . . ?
C18 C17 H17 119.7 . . ?
C16 C17 C18 120.60(14) . . ?
C16 C17 H17 119.7 . . ?
C16 C15 H15 120.5 . . ?
C14 C15 C16 118.97(14) . . ?
C14 C15 H15 120.5 . . ?
C13 C14 H14 118.9 . . ?
C15 C14 C13 122.14(14) . . ?
C15 C14 H14 118.9 . . ?
C11 C10 C9 119.97(14) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C5 C4 H4 120.9 . . ?
C5 C4 C3 118.15(14) . . ?
C3 C4 H4 120.9 . . ?
C1 C2 H2A 121.2 . . ?
C1 C2 C3 117.55(14) . . ?
C3 C2 H2A 121.2 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.10(14) . . ?
C2 C3 H3 120.0 . . ?

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 C19 O2 176.22(13) . . . . ?
N1 C1 C19 N5 -4.55(17) . . . . ?
N1 C1 C2 C3 1.2(2) . . . . ?
N1 C5 C6 O1 167.45(14) . . . . ?
N1 C5 C6 N2 -10.68(16) . . . . ?
N1 C5 C4 C3 0.5(2) . . . . ?
N3 N4 C13 C18 2.2(2) . . . . ?
N3 N4 C13 C14 -179.28(12) . . . . ?
N3 C12 C7 N2 3.80(18) . . . . ?
N3 C12 C7 C8 -177.83(12) . . . . ?
N3 C12 C11 C10 177.90(13) . . . . ?
N2 C7 C8 C9 177.92(14) . . . . ?
N5 C18 C13 N4 -1.9(2) . . . . ?
N5 C18 C13 C14 179.69(13) . . . . ?
N5 C18 C17 C16 179.81(13) . . . . ?
N4 N3 C12 C7 -173.26(12) . . . . ?
N4 N3 C12 C11 9.06(19) . . . . ?
N4 C13 C14 C15 -178.26(13) . . . . ?
C12 N3 N4 C13 -177.64(11) . . . . ?
C12 C7 C8 C9 -0.3(2) . . . . ?
C12 C11 C10 C9 -0.3(2) . . . . ?
C18 N5 C19 O2 0.3(2) . . . . ?
C18 N5 C19 C1 -178.92(13) . . . . ?
C18 C13 C14 C15 0.5(2) . . . . ?
C7 N2 C6 O1 -26.0(3) . . . . ?
C7 N2 C6 C5 152.03(15) . . . . ?
C7 C12 C11 C10 0.3(2) . . . . ?
C7 C8 C9 C10 0.4(2) . . . . ?
C16 C15 C14 C13 0.1(2) . . . . ?
C13 C18 C17 C16 0.0(2) . . . . ?
C1 N1 C5 C6 -173.05(12) . . . . ?
C1 N1 C5 C4 2.1(2) . . . . ?
C1 C2 C3 C4 1.4(2) . . . . ?
C5 N1 C1 C19 174.10(12) . . . . ?
C5 N1 C1 C2 -3.0(2) . . . . ?
C5 C4 C3 C2 -2.2(2) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C11 C12 C7 N2 -178.38(13) . . . . ?
C11 C12 C7 C8 0.0(2) . . . . ?
C19 N5 C18 C13 177.98(13) . . . . ?
C19 N5 C18 C17 -1.8(2) . . . . ?
C19 C1 C2 C3 -175.59(13) . . . . ?
C6 N2 C7 C12 -145.23(15) . . . . ?
C6 N2 C7 C8 36.5(2) . . . . ?
C6 C5 C4 C3 175.01(14) . . . . ?
C17 C18 C13 N4 177.95(13) . . . . ?
C17 C18 C13 C14 -0.5(2) . . . . ?
C17 C16 C15 C14 -0.6(2) . . . . ?
C15 C16 C17 C18 0.5(2) . . . . ?
C4 C5 C6 O1 -7.5(2) . . . . ?
C4 C5 C6 N2 174.38(14) . . . . ?
C2 C1 C19 O2 -6.7(2) . . . . ?
C2 C1 C19 N5 172.51(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: THF/Water'
####################################################################### 
# 
# 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_d1_a
_database_code_depnum_ccdc_archive 'CCDC 2202809'
loop_
_audit_author_name
_audit_author_address
'Dibyajyoti Pathak'
;Indian Institute of Science Education and Research,Bhopal
India
;
_audit_update_record             
;
2022-08-22 deposited with the CCDC.	2022-10-10 downloaded from the CCDC.
;
_audit_creation_date             2022-08-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            RedcDP2
_chemical_name_systematic        ReducedcycloDiazoP2
_chemical_formula_moiety         'C19 H17 N5 O2'
_chemical_formula_sum            'C19 H17 N5 O2'
_chemical_formula_weight         347.38
_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'
O O 0.0106 0.0060 '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                   10.3311(6)
_cell_length_b                   18.0936(9)
_cell_length_c                   8.8295(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.013(2)
_cell_angle_gamma                90
_cell_volume                     1638.12(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7746
_cell_measurement_temperature    140.0
_cell_measurement_theta_max      29.75
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6927
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1050 before and 0.0638 after correction.
The Ratio of minimum to maximum transmission is 0.9286.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_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  0.1038
_diffrn_reflns_av_unetI/netI     0.0895
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            32357
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.091
_diffrn_reflns_theta_min         2.283
_diffrn_ambient_temperature      140.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_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                2965
_reflns_number_total             4817
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4817
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1460
_refine_ls_R_factor_gt           0.0779
_refine_ls_restrained_S_all      1.056
_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)+(0.0408P)²+1.8860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1523
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2.a Rotating group:
 N5(H5A,H5B)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2A), C9(H9), C15(H15), C18(H18), C4(H4), C12(H12), C2(H2B), C10(H10),
 C3(H3), C11(H11), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.04497(16) 0.56235(9) 0.82106(17) 0.0250(4) Uani 1 1 d . . . . .
O2 O 0.18212(18) 0.64318(10) 0.06928(18) 0.0269(4) Uani 1 1 d . . . . .
N1 N 0.13819(17) 0.57526(10) 0.44809(19) 0.0163(4) Uani 1 1 d . . . . .
N2 N 0.16891(17) 0.48696(10) 0.68797(19) 0.0173(4) Uani 1 1 d . . . . .
H2A H 0.193381 0.481553 0.596578 0.021 Uiso 1 1 calc R U . . .
N3 N 0.35295(18) 0.39990(10) 0.6081(2) 0.0179(4) Uani 1 1 d . . . . .
N4 N 0.44705(18) 0.36081(10) 0.5753(2) 0.0198(4) Uani 1 1 d . . . . .
N5 N 0.6406(2) 0.27618(11) 0.4836(2) 0.0297(5) Uani 1 1 d . . . . .
H5A H 0.580052 0.260081 0.538060 0.036 Uiso 1 1 d R U . . .
H5B H 0.664148 0.239643 0.426463 0.036 Uiso 1 1 d R U . . .
C1 C 0.0712(2) 0.59336(12) 0.5635(2) 0.0172(4) Uani 1 1 d . . . . .
C8 C 0.2150(2) 0.43288(11) 0.7941(2) 0.0166(4) Uani 1 1 d . . . . .
C7 C 0.0929(2) 0.54600(12) 0.7044(2) 0.0183(5) Uani 1 1 d . . . . .
C9 C 0.1689(2) 0.42407(12) 0.9353(2) 0.0196(5) Uani 1 1 d . . . . .
H9 H 0.104483 0.456589 0.965220 0.024 Uiso 1 1 calc R U . . .
C5 C 0.1240(2) 0.61847(12) 0.3243(2) 0.0174(5) Uani 1 1 d . . . . .
C13 C 0.3114(2) 0.38474(12) 0.7522(2) 0.0184(5) Uani 1 1 d . . . . .
C14 C 0.4907(2) 0.37857(12) 0.4343(2) 0.0193(5) Uani 1 1 d . . . . .
C15 C 0.4452(2) 0.43797(13) 0.3420(3) 0.0226(5) Uani 1 1 d . . . . .
H15 H 0.378489 0.468799 0.372113 0.027 Uiso 1 1 calc R U . . .
C18 C 0.6420(2) 0.34940(13) 0.2545(3) 0.0229(5) Uani 1 1 d . . . . .
H18 H 0.709780 0.319767 0.223088 0.027 Uiso 1 1 calc R U . . .
C19 C 0.5920(2) 0.33307(12) 0.3921(3) 0.0207(5) Uani 1 1 d . . . . .
C4 C 0.0433(2) 0.67982(12) 0.3116(3) 0.0227(5) Uani 1 1 d . . . . .
H4 H 0.036373 0.709825 0.222700 0.027 Uiso 1 1 calc R U . . .
C12 C 0.3572(2) 0.32737(13) 0.8490(3) 0.0230(5) Uani 1 1 d . . . . .
H12 H 0.420544 0.293996 0.819428 0.028 Uiso 1 1 calc R U . . .
C2 C -0.0130(2) 0.65291(13) 0.5596(3) 0.0229(5) Uani 1 1 d . . . . .
H2B H -0.059690 0.663388 0.643320 0.028 Uiso 1 1 calc R U . . .
C10 C 0.2178(2) 0.36779(13) 1.0307(3) 0.0240(5) Uani 1 1 d . . . . .
H10 H 0.187443 0.362275 1.127382 0.029 Uiso 1 1 calc R U . . .
C3 C -0.0273(2) 0.69670(13) 0.4307(3) 0.0267(5) Uani 1 1 d . . . . .
H3 H -0.084813 0.737863 0.423749 0.032 Uiso 1 1 calc R U . . .
C11 C 0.3107(2) 0.31891(13) 0.9881(3) 0.0261(5) Uani 1 1 d . . . . .
H11 H 0.342104 0.279820 1.054438 0.031 Uiso 1 1 calc R U . . .
C16 C 0.4956(2) 0.45249(14) 0.2083(3) 0.0261(5) Uani 1 1 d . . . . .
H16 H 0.463605 0.492810 0.145675 0.031 Uiso 1 1 calc R U . . .
C6 C 0.2053(2) 0.59698(13) 0.2003(2) 0.0232(5) Uani 1 1 d . . . . .
H6A H 0.298783 0.599743 0.241218 0.028 Uiso 1 1 calc R U . . .
H6B H 0.185590 0.545151 0.169862 0.028 Uiso 1 1 calc R U . . .
C17 C 0.5941(2) 0.40734(14) 0.1657(3) 0.0262(5) Uani 1 1 d . . . . .
H17 H 0.628711 0.417063 0.072867 0.031 Uiso 1 1 calc R U . . .
H2 H 0.129(3) 0.6198(18) 0.002(4) 0.052(10) Uiso 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
O1 C7 1.232(2) . ?
O2 C6 1.424(3) . ?
O2 H2 0.87(3) . ?
N1 C1 1.341(3) . ?
N1 C5 1.337(3) . ?
N2 H2A 0.8800 . ?
N2 C8 1.397(3) . ?
N2 C7 1.344(3) . ?
N3 N4 1.264(2) . ?
N3 C13 1.419(3) . ?
N4 C14 1.412(3) . ?
N5 H5A 0.8836 . ?
N5 H5B 0.8837 . ?
N5 C19 1.366(3) . ?
C1 C7 1.505(3) . ?
C1 C2 1.382(3) . ?
C8 C9 1.396(3) . ?
C8 C13 1.406(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(3) . ?
C5 C4 1.385(3) . ?
C5 C6 1.510(3) . ?
C13 C12 1.390(3) . ?
C14 C15 1.395(3) . ?
C14 C19 1.416(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.372(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.409(3) . ?
C18 C17 1.365(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.385(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.381(3) . ?
C2 H2B 0.9500 . ?
C2 C3 1.380(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(3) . ?
C3 H3 0.9500 . ?
C11 H11 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.392(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C17 H17 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
C6 O2 H2 107(2) . . ?
C5 N1 C1 117.61(18) . . ?
C8 N2 H2A 115.1 . . ?
C7 N2 H2A 115.1 . . ?
C7 N2 C8 129.74(18) . . ?
N4 N3 C13 115.02(18) . . ?
N3 N4 C14 114.33(18) . . ?
H5A N5 H5B 109.1 . . ?
C19 N5 H5A 109.7 . . ?
C19 N5 H5B 109.4 . . ?
N1 C1 C7 116.81(18) . . ?
N1 C1 C2 123.6(2) . . ?
C2 C1 C7 119.62(19) . . ?
N2 C8 C13 116.83(18) . . ?
C9 C8 N2 123.6(2) . . ?
C9 C8 C13 119.6(2) . . ?
O1 C7 N2 125.5(2) . . ?
O1 C7 C1 121.3(2) . . ?
N2 C7 C1 113.13(18) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(2) . . ?
C10 C9 H9 120.3 . . ?
N1 C5 C4 122.6(2) . . ?
N1 C5 C6 115.28(19) . . ?
C4 C5 C6 122.1(2) . . ?
C8 C13 N3 114.70(19) . . ?
C12 C13 N3 125.3(2) . . ?
C12 C13 C8 120.0(2) . . ?
N4 C14 C19 115.2(2) . . ?
C15 C14 N4 124.7(2) . . ?
C15 C14 C19 120.1(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.5 . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.7(2) . . ?
N5 C19 C14 120.9(2) . . ?
N5 C19 C18 121.4(2) . . ?
C18 C19 C14 117.7(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 H4 120.6 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
C1 C2 H2B 120.9 . . ?
C3 C2 C1 118.2(2) . . ?
C3 C2 H2B 120.9 . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.2(2) . . ?
C11 C10 H10 119.4 . . ?
C4 C3 H3 120.5 . . ?
C2 C3 C4 119.1(2) . . ?
C2 C3 H3 120.5 . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.1(2) . . ?
C17 C16 H16 120.4 . . ?
O2 C6 C5 112.63(19) . . ?
O2 C6 H6A 109.1 . . ?
O2 C6 H6B 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C18 C17 C16 121.4(2) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C7 O1 173.3(2) . . . . ?
N1 C1 C7 N2 -6.0(3) . . . . ?
N1 C1 C2 C3 -1.0(3) . . . . ?
N1 C5 C4 C3 -1.0(3) . . . . ?
N1 C5 C6 O2 177.63(19) . . . . ?
N2 C8 C9 C10 178.2(2) . . . . ?
N2 C8 C13 N3 2.5(3) . . . . ?
N2 C8 C13 C12 -176.9(2) . . . . ?
N3 N4 C14 C15 5.8(3) . . . . ?
N3 N4 C14 C19 -177.13(19) . . . . ?
N3 C13 C12 C11 178.9(2) . . . . ?
N4 N3 C13 C8 174.38(19) . . . . ?
N4 N3 C13 C12 -6.3(3) . . . . ?
N4 C14 C15 C16 178.2(2) . . . . ?
N4 C14 C19 N5 0.6(3) . . . . ?
N4 C14 C19 C18 -178.33(19) . . . . ?
C1 N1 C5 C4 -0.4(3) . . . . ?
C1 N1 C5 C6 177.95(19) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C8 N2 C7 O1 -2.3(4) . . . . ?
C8 N2 C7 C1 176.9(2) . . . . ?
C8 C9 C10 C11 -1.0(3) . . . . ?
C8 C13 C12 C11 -1.8(3) . . . . ?
C7 N2 C8 C9 11.8(3) . . . . ?
C7 N2 C8 C13 -169.2(2) . . . . ?
C7 C1 C2 C3 177.8(2) . . . . ?
C9 C8 C13 N3 -178.59(19) . . . . ?
C9 C8 C13 C12 2.0(3) . . . . ?
C9 C10 C11 C12 1.2(4) . . . . ?
C5 N1 C1 C7 -177.43(18) . . . . ?
C5 N1 C1 C2 1.4(3) . . . . ?
C5 C4 C3 C2 1.4(4) . . . . ?
C13 N3 N4 C14 -177.58(18) . . . . ?
C13 C8 C9 C10 -0.7(3) . . . . ?
C13 C12 C11 C10 0.2(4) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C15 C14 C19 N5 177.8(2) . . . . ?
C15 C14 C19 C18 -1.1(3) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C19 C14 C15 C16 1.2(3) . . . . ?
C19 C18 C17 C16 0.6(4) . . . . ?
C4 C5 C6 O2 -4.0(3) . . . . ?
C2 C1 C7 O1 -5.6(3) . . . . ?
C2 C1 C7 N2 175.1(2) . . . . ?
C6 C5 C4 C3 -179.2(2) . . . . ?
C17 C18 C19 N5 -178.7(2) . . . . ?
C17 C18 C19 C14 0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform/Ethylacetate'
