# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 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_24julb_a
_database_code_depnum_ccdc_archive 'CCDC 2113929'
loop_
_audit_author_name
_audit_author_address
'Srinivas Dharavath'
;IIT kanpur
India
;
_audit_update_record             
;
2021-10-05 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_audit_creation_date             2021-09-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        AVR08
_chemical_formula_moiety         'C1.5 H N4, C2 H6 N5'
_chemical_formula_sum            'C3.50 H6 N9'
_chemical_formula_weight         174.17
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   22.1531(14)
_cell_length_b                   31.6998(18)
_cell_length_c                   4.0893(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2871.7(3)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    4621
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      3.16
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7134
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1347 before and 0.0476 after correction.
The Ratio of minimum to maximum transmission is 0.9573.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1440
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            8069
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.039
_diffrn_reflns_theta_max         25.039
_diffrn_reflns_theta_min         3.161
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II 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         0.735
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1238
_reflns_number_total             1261
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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         0.113
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 522 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1261
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0250
_refine_ls_restrained_S_all      1.095
_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)+(0.0333P)²+1.9338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0622
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
2. Others
 Fixed Sof: H6A(0.5) H6B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
3.b X=CH2 refined with riding coordinates:
 N12(H12A,H12B), N7(H7A,H7B)
;
_atom_sites_solution_hydrogens   mixed
_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
N4 N 0.30466(7) 0.30307(5) 0.1915(4) 0.0155(4) Uani 1 1 d . . . . .
N13 N 0.18227(7) 0.40210(5) 0.8360(4) 0.0151(4) Uani 1 1 d . . . . .
N3 N 0.35661(7) 0.30306(5) 0.0192(5) 0.0169(4) Uani 1 1 d . . . . .
N9 N 0.27598(7) 0.39914(5) 0.6472(5) 0.0185(4) Uani 1 1 d . . . . .
N2 N 0.38311(7) 0.26600(5) 0.0498(5) 0.0180(4) Uani 1 1 d . . . . .
N1 N 0.34890(8) 0.24094(5) 0.2419(4) 0.0174(4) Uani 1 1 d . . . . .
N10 N 0.24100(7) 0.36536(5) 0.5318(5) 0.0178(4) Uani 1 1 d . . . . .
N12 N 0.14023(7) 0.34103(5) 0.5836(5) 0.0213(4) Uani 1 1 d . . . . .
H12A H 0.145894 0.319249 0.453754 0.026 Uiso 1 1 calc R U . . .
H12B H 0.104616 0.345344 0.672861 0.026 Uiso 1 1 calc R U . . .
N7 N 0.25004(8) 0.45734(5) 0.9792(5) 0.0251(5) Uani 1 1 d . . . . .
H7A H 0.286028 0.468918 0.963436 0.030 Uiso 1 1 calc R U . . .
H7B H 0.221685 0.469727 1.095294 0.030 Uiso 1 1 calc R U . . .
C8 C 0.23841(8) 0.42076(6) 0.8261(5) 0.0168(4) Uani 1 1 d . . . . .
C11 C 0.18532(9) 0.36730(6) 0.6449(5) 0.0158(5) Uani 1 1 d . . . . .
C5 C 0.30175(9) 0.26481(6) 0.3255(5) 0.0143(4) Uani 1 1 d . . . . .
C6 C 0.250000 0.250000 0.5327(7) 0.0166(6) Uani 1 2 d S T P . .
H6A H 0.263704 0.226618 0.674977 0.020 Uiso 0.5 1 calc R U P . .
H6B H 0.236297 0.273380 0.675003 0.020 Uiso 0.5 1 calc R U P . .
H13 H 0.1509(12) 0.4118(7) 0.955(7) 0.027(7) Uiso 1 1 d . . . . .
H10 H 0.2583(12) 0.3445(8) 0.396(8) 0.041(8) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N4 0.0138(8) 0.0163(9) 0.0163(10) -0.0011(8) 0.0019(7) -0.0004(7)
N13 0.0136(8) 0.0146(8) 0.0172(9) -0.0018(7) 0.0027(8) 0.0004(7)
N3 0.0160(8) 0.0180(8) 0.0168(8) -0.0004(7) 0.0022(8) -0.0004(6)
N9 0.0154(9) 0.0151(9) 0.0251(10) -0.0018(7) 0.0030(8) -0.0016(7)
N2 0.0155(8) 0.0191(9) 0.0194(9) 0.0007(8) 0.0013(8) 0.0010(7)
N1 0.0162(8) 0.0173(8) 0.0188(9) 0.0026(7) -0.0009(7) 0.0002(7)
N10 0.0137(9) 0.0171(9) 0.0226(9) -0.0032(8) 0.0044(8) -0.0006(7)
N12 0.0147(8) 0.0191(9) 0.0302(11) -0.0098(9) 0.0052(9) -0.0002(7)
N7 0.0176(9) 0.0213(9) 0.0364(12) -0.0080(8) 0.0060(8) -0.0054(7)
C8 0.0149(9) 0.0158(10) 0.0196(10) 0.0020(9) 0.0012(9) 0.0001(8)
C11 0.0158(10) 0.0144(10) 0.0173(11) 0.0016(8) 0.0007(9) 0.0024(8)
C5 0.0152(10) 0.0159(10) 0.0117(10) -0.0016(8) -0.0031(8) -0.0019(8)
C6 0.0176(14) 0.0181(14) 0.0140(14) 0.000 0.000 -0.0021(11)

_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
N4 N3 1.349(2) . ?
N4 C5 1.332(2) . ?
N13 C8 1.378(2) . ?
N13 C11 1.353(3) . ?
N13 H13 0.90(3) . ?
N3 N2 1.319(2) . ?
N9 N10 1.403(2) . ?
N9 C8 1.303(3) . ?
N2 N1 1.350(2) . ?
N1 C5 1.334(3) . ?
N10 C11 1.319(3) . ?
N10 H10 0.94(3) . ?
N12 H12A 0.8800 . ?
N12 H12B 0.8800 . ?
N12 C11 1.325(3) . ?
N7 H7A 0.8800 . ?
N7 H7B 0.8800 . ?
N7 C8 1.343(3) . ?
C5 C6 1.501(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N4 N3 104.83(15) . . ?
C8 N13 H13 124.5(15) . . ?
C11 N13 C8 106.73(17) . . ?
C11 N13 H13 128.7(15) . . ?
N2 N3 N4 109.28(16) . . ?
C8 N9 N10 103.74(15) . . ?
N3 N2 N1 109.24(16) . . ?
C5 N1 N2 104.76(15) . . ?
N9 N10 H10 120.4(16) . . ?
C11 N10 N9 111.27(17) . . ?
C11 N10 H10 128.3(16) . . ?
H12A N12 H12B 120.0 . . ?
C11 N12 H12A 120.0 . . ?
C11 N12 H12B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C8 N7 H7A 120.0 . . ?
C8 N7 H7B 120.0 . . ?
N9 C8 N13 111.55(17) . . ?
N9 C8 N7 126.40(18) . . ?
N7 C8 N13 122.02(19) . . ?
N10 C11 N13 106.69(18) . . ?
N10 C11 N12 127.56(19) . . ?
N12 C11 N13 125.74(18) . . ?
N4 C5 N1 111.89(17) . . ?
N4 C5 C6 123.64(15) . . ?
N1 C5 C6 124.41(15) . . ?
C5 C6 C5 111.3(2) 14 . ?
C5 C6 H6A 109.4 14 . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 14 . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?

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
N4 N3 N2 N1 0.2(2) . . . . ?
N4 C5 C6 C5 81.73(19) . . . 14 ?
N3 N4 C5 N1 -0.7(2) . . . . ?
N3 N4 C5 C6 -178.08(19) . . . . ?
N3 N2 N1 C5 -0.6(2) . . . . ?
N9 N10 C11 N13 0.0(2) . . . . ?
N9 N10 C11 N12 179.2(2) . . . . ?
N2 N1 C5 N4 0.9(2) . . . . ?
N2 N1 C5 C6 178.19(19) . . . . ?
N1 C5 C6 C5 -95.29(19) . . . 14 ?
N10 N9 C8 N13 1.3(2) . . . . ?
N10 N9 C8 N7 -176.9(2) . . . . ?
C8 N13 C11 N10 0.8(2) . . . . ?
C8 N13 C11 N12 -178.4(2) . . . . ?
C8 N9 N10 C11 -0.8(2) . . . . ?
C11 N13 C8 N9 -1.4(2) . . . . ?
C11 N13 C8 N7 176.92(19) . . . . ?
C5 N4 N3 N2 0.3(2) . . . . ?

_shelx_res_file                  
;
TITL 24julb_a_a.res in Fdd2
    24julb_a.res
    created by SHELXL-2018/3 at 18:45:34 on 22-Sep-2021
REM Old TITL 24julb_a_a.res in Fdd2
REM SHELXT solution in Fdd2: R1 0.086, Rweak 0.022, Alpha 0.001
REM <I/s> 0.618 for 38 systematic absences, Orientation as input
REM Flack x = -9.990 ( 9.990 ) from 525 Parsons' quotients
REM Formula found by SHELXT: C25
CELL 0.71073 22.1531 31.6998 4.0893 90 90 90
ZERR 16 0.0014 0.0018 0.0002 0 0 0
LATT -4
SYMM -X,-Y,+Z
SYMM 0.25+X,0.25-Y,0.25+Z
SYMM 0.25-X,0.25+Y,0.25+Z
SFAC C H N
UNIT 56 96 144

L.S. 20
PLAN  1
SIZE 0.1 0.25 0.1
TEMP -173.15
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2
acta
OMIT 2 2 0
REM <olex2.extras>
REM <HklSrc "%.\\24julb_a.hkl">
REM </olex2.extras>

WGHT    0.033300    1.933800
FVAR       0.31939
N4    3    0.304662    0.303066    0.191491    11.00000    0.01385    0.01627 =
         0.01631   -0.00112    0.00188   -0.00044
N13   3    0.182275    0.402100    0.835963    11.00000    0.01358    0.01459 =
         0.01717   -0.00177    0.00265    0.00035
N3    3    0.356607    0.303056    0.019154    11.00000    0.01596    0.01804 =
         0.01678   -0.00041    0.00224   -0.00039
N9    3    0.275978    0.399139    0.647202    11.00000    0.01541    0.01507 =
         0.02514   -0.00177    0.00305   -0.00157
N2    3    0.383106    0.266004    0.049791    11.00000    0.01553    0.01910 =
         0.01938    0.00066    0.00133    0.00104
N1    3    0.348900    0.240941    0.241941    11.00000    0.01621    0.01726 =
         0.01884    0.00263   -0.00092    0.00023
N10   3    0.241002    0.365359    0.531776    11.00000    0.01365    0.01707 =
         0.02264   -0.00323    0.00436   -0.00063
N12   3    0.140234    0.341026    0.583648    11.00000    0.01475    0.01907 =
         0.03022   -0.00982    0.00519   -0.00018
AFIX  93
H12A  2    0.145894    0.319249    0.453754    11.00000   -1.20000
H12B  2    0.104616    0.345344    0.672861    11.00000   -1.20000
AFIX   0
N7    3    0.250045    0.457336    0.979192    11.00000    0.01762    0.02129 =
         0.03638   -0.00805    0.00605   -0.00541
AFIX  93
H7A   2    0.286028    0.468918    0.963436    11.00000   -1.20000
H7B   2    0.221685    0.469727    1.095294    11.00000   -1.20000
AFIX   0
C8    1    0.238412    0.420755    0.826067    11.00000    0.01491    0.01577 =
         0.01962    0.00199    0.00123    0.00012
C11   1    0.185324    0.367304    0.644877    11.00000    0.01578    0.01437 =
         0.01734    0.00159    0.00071    0.00237

C5    1    0.301750    0.264815    0.325537    11.00000    0.01522    0.01594 =
         0.01168   -0.00165   -0.00305   -0.00195
C6    1    0.250000    0.250000    0.532690    10.50000    0.01760    0.01812 =
         0.01397    0.00000    0.00000   -0.00208
AFIX  23
H6A   2    0.263704    0.226618    0.674977    10.50000   -1.20000
H6B   2    0.236297    0.273380    0.675003    10.50000   -1.20000
AFIX   0

H13   2    0.150856    0.411754    0.954622    11.00000    0.02737
H10   2    0.258335    0.344534    0.396360    11.00000    0.04101
HKLF 4




REM  24julb_a_a.res in Fdd2
REM wR2 = 0.0622, GooF = S = 1.095, Restrained GooF = 1.095 for all data
REM R1 = 0.0250 for 1238 Fo > 4sig(Fo) and 0.0257 for all 1261 data
REM 122 parameters refined using 1 restraints

END

WGHT      0.0334      1.9288

REM Highest difference peak  0.113,  deepest hole -0.165,  1-sigma level  0.036
Q1    1   0.0819  0.3851  0.5694  11.00000  0.05    0.11
;
_shelx_res_checksum              48394
_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_2epa_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2113930'
loop_
_audit_author_name
_audit_author_address
'Srinivas Dharavath'
;IIT kanpur
India
;
_audit_update_record             
;
2021-10-05 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_audit_creation_date             2021-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2.5 H2 N5 O2, C H7 N4'
_chemical_formula_sum            'C3.50 H9 N9 O2'
_chemical_formula_weight         209.20
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.179(2)
_cell_length_b                   4.4387(7)
_cell_length_c                   23.433(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.747(5)
_cell_angle_gamma                90
_cell_volume                     1677.1(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5686
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.56
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1152 before and 0.0532 after correction. The Ratio of minimum to maximum transmission is 0.8756. The λ/2 correction factor is Not present.'
_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    1.657
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             872
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11337
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.949
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1796
_reflns_number_total             2011
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2011
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.035
_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)+(0.0276P)²+2.1522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0861
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups
2. Others
 Fixed Sof: H10A(0.5) H10B(0.5)
3.a Rotating group:
 N11(H11A,H11B)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 N12(H12)
3.d X=CH2 refined with riding coordinates:
 N15(H15A,H15B), N14(H14A,H14B)
;
_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 0.22866(6) 0.2728(2) 0.43100(4) 0.0246(2) Uani 1 1 d . . . . .
O2 O 0.27627(6) 0.4768(2) 0.35493(4) 0.0277(2) Uani 1 1 d . . . . .
N4 N 0.14705(6) 0.5721(2) 0.37851(4) 0.0189(2) Uani 1 1 d . . . . .
N9 N 0.06098(6) 0.8925(2) 0.32202(4) 0.0178(2) Uani 1 1 d . . . . .
N3 N 0.21889(6) 0.4406(3) 0.38720(4) 0.0193(2) Uani 1 1 d . . . . .
N11 N 0.38024(7) -0.3533(2) 0.49612(5) 0.0207(2) Uani 1 1 d . . . . .
H11A H 0.373359 -0.274722 0.528919 0.025 Uiso 1 1 d GR . . . .
H11B H 0.343831 -0.492229 0.488767 0.025 Uiso 1 1 d GR . . . .
N6 N 0.18674(7) 0.8679(3) 0.29430(4) 0.0198(2) Uani 1 1 d . . . . .
N7 N 0.14545(7) 1.0693(2) 0.25773(4) 0.0211(2) Uani 1 1 d . . . . .
N15 N 0.50820(6) -0.1879(2) 0.43572(5) 0.0207(2) Uani 1 1 d . . . . .
H15A H 0.550552 -0.138496 0.416379 0.025 Uiso 1 1 calc R . . . .
H15B H 0.514207 -0.325423 0.462797 0.025 Uiso 1 1 calc R . . . .
N12 N 0.37105(6) -0.1287(2) 0.45355(5) 0.0208(2) Uani 1 1 d . . . . .
H12 H 0.323118 -0.036826 0.446373 0.025 Uiso 1 1 calc R . . . .
N14 N 0.42504(7) 0.1519(3) 0.38353(5) 0.0230(2) Uani 1 1 d . . . . .
H14A H 0.466762 0.203893 0.363800 0.028 Uiso 1 1 calc R . . . .
H14B H 0.376276 0.237811 0.376324 0.028 Uiso 1 1 calc R . . . .
C8 C 0.07033(8) 1.0736(3) 0.27629(5) 0.0175(2) Uani 1 1 d . . . . .
C5 C 0.13546(7) 0.7664(3) 0.33232(5) 0.0168(2) Uani 1 1 d . . . . .
C13 C 0.43565(7) -0.0558(3) 0.42410(5) 0.0184(3) Uani 1 1 d . . . . .
C10 C 0.000000 1.2625(4) 0.250000 0.0200(4) Uani 1 2 d S T P . .
H10A H -0.020749 1.393778 0.279841 0.024 Uiso 0.5 1 calc R . . . .
H10B H 0.020748 1.393787 0.220160 0.024 Uiso 0.5 1 calc R . . . .
H6 H 0.2396(11) 0.812(4) 0.2918(7) 0.034(5) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0213(4) 0.0318(5) 0.0211(5) 0.0086(4) 0.0034(3) 0.0015(4)
O2 0.0182(4) 0.0403(6) 0.0257(5) 0.0089(4) 0.0083(4) 0.0034(4)
N4 0.0162(5) 0.0225(5) 0.0184(5) 0.0032(4) 0.0030(4) 0.0005(4)
N9 0.0195(5) 0.0173(5) 0.0166(5) 0.0004(4) 0.0014(4) -0.0008(4)
N3 0.0164(5) 0.0234(5) 0.0181(5) 0.0005(4) 0.0017(4) -0.0019(4)
N11 0.0215(5) 0.0193(5) 0.0219(5) 0.0005(4) 0.0055(4) -0.0025(4)
N6 0.0195(5) 0.0231(5) 0.0171(5) 0.0019(4) 0.0034(4) -0.0015(4)
N7 0.0241(5) 0.0218(5) 0.0175(5) 0.0021(4) 0.0022(4) -0.0004(4)
N15 0.0178(5) 0.0220(5) 0.0232(5) 0.0016(4) 0.0071(4) -0.0003(4)
N12 0.0172(5) 0.0224(5) 0.0236(5) 0.0030(4) 0.0056(4) 0.0007(4)
N14 0.0174(5) 0.0266(6) 0.0258(6) 0.0041(5) 0.0059(4) 0.0005(4)
C8 0.0231(6) 0.0147(5) 0.0145(5) -0.0025(4) 0.0010(4) -0.0027(5)
C5 0.0180(5) 0.0175(5) 0.0150(5) -0.0025(4) 0.0021(4) -0.0036(5)
C13 0.0193(6) 0.0174(6) 0.0186(6) -0.0050(4) 0.0031(4) -0.0031(5)
C10 0.0261(9) 0.0151(8) 0.0186(8) 0.000 0.0010(7) 0.000

_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 N3 1.2677(14) . ?
O2 N3 1.2552(13) . ?
N4 N3 1.3014(15) . ?
N4 C5 1.3848(15) . ?
N9 C8 1.3580(16) . ?
N9 C5 1.3324(16) . ?
N11 H11A 0.8597 . ?
N11 H11B 0.8601 . ?
N11 N12 1.4096(15) . ?
N6 N7 1.3731(15) . ?
N6 C5 1.3442(15) . ?
N6 H6 0.897(18) . ?
N7 C8 1.3243(16) . ?
N15 H15A 0.8800 . ?
N15 H15B 0.8800 . ?
N15 C13 1.3202(16) . ?
N12 H12 0.8800 . ?
N12 C13 1.3388(16) . ?
N14 H14A 0.8800 . ?
N14 H14B 0.8800 . ?
N14 C13 1.3252(16) . ?
C8 C10 1.5038(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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
N3 N4 C5 117.58(10) . . ?
C5 N9 C8 103.49(10) . . ?
O1 N3 N4 116.11(10) . . ?
O2 N3 O1 120.94(10) . . ?
O2 N3 N4 122.95(11) . . ?
H11A N11 H11B 109.4 . . ?
N12 N11 H11A 109.4 . . ?
N12 N11 H11B 109.6 . . ?
N7 N6 H6 123.8(11) . . ?
C5 N6 N7 109.68(10) . . ?
C5 N6 H6 126.5(11) . . ?
C8 N7 N6 102.51(10) . . ?
H15A N15 H15B 120.0 . . ?
C13 N15 H15A 120.0 . . ?
C13 N15 H15B 120.0 . . ?
N11 N12 H12 120.2 . . ?
C13 N12 N11 119.65(10) . . ?
C13 N12 H12 120.2 . . ?
H14A N14 H14B 120.0 . . ?
C13 N14 H14A 120.0 . . ?
C13 N14 H14B 120.0 . . ?
N9 C8 C10 121.56(10) . . ?
N7 C8 N9 114.57(11) . . ?
N7 C8 C10 123.87(10) . . ?
N9 C5 N4 117.72(10) . . ?
N9 C5 N6 109.74(11) . . ?
N6 C5 N4 132.51(11) . . ?
N15 C13 N12 120.33(12) . . ?
N15 C13 N14 121.14(11) . . ?
N14 C13 N12 118.53(11) . . ?
C8 C10 C8 112.22(14) 2 . ?
C8 C10 H10A 109.2 2 . ?
C8 C10 H10A 109.2 . . ?
C8 C10 H10B 109.2 . . ?
C8 C10 H10B 109.2 2 . ?
H10A C10 H10B 107.9 . . ?

_shelx_res_file                  
;
TITL 2epa_0m_a.res in C2/c
    2epa_0m_a.res
    created by SHELXL-2018/1 at 16:51:21 on 02-Sep-2021
REM Old TITL 2epa_0m in C2/c
REM SHELXT solution in C2/c
REM R1 0.137, Rweak 0.002, Alpha 0.012, Orientation as input
REM Formula found by SHELXT: C21 O8
CELL 0.71073 16.1791 4.4387 23.4331 90 94.747 90
ZERR 8 0.0023 0.0007 0.0035 0 0.005 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H N O
UNIT 28 72 72 16

L.S. 10
PLAN  20
SIZE 0.32 0.22 0.13
TEMP -173.15
BOND $H
LIST 6
fmap 2
acta
OMIT -2 56
REM <olex2.extras>
REM <HklSrc "%.\\2epa_0m_a.hkl">
REM </olex2.extras>

WGHT    0.027600    2.152200
FVAR       0.61626
O1    4    0.228655    0.272763    0.431002    11.00000    0.02128    0.03183 =
         0.02111    0.00860    0.00343    0.00149
O2    4    0.276275    0.476810    0.354935    11.00000    0.01822    0.04032 =
         0.02572    0.00893    0.00825    0.00335
N4    3    0.147051    0.572060    0.378507    11.00000    0.01620    0.02246 =
         0.01841    0.00320    0.00298    0.00045
N9    3    0.060984    0.892500    0.322019    11.00000    0.01950    0.01731 =
         0.01665    0.00044    0.00142   -0.00081
N3    3    0.218893    0.440636    0.387198    11.00000    0.01644    0.02343 =
         0.01812    0.00045    0.00172   -0.00191
N11   3    0.380236   -0.353347    0.496120    11.00000    0.02148    0.01928 =
         0.02191    0.00052    0.00548   -0.00251
AFIX   7
H11A  2    0.373359   -0.274722    0.528919    11.00000   -1.20000
H11B  2    0.343831   -0.492229    0.488767    11.00000   -1.20000
AFIX   0

N6    3    0.186740    0.867906    0.294304    11.00000    0.01948    0.02308 =
         0.01710    0.00194    0.00343   -0.00150
N7    3    0.145451    1.069330    0.257731    11.00000    0.02409    0.02181 =
         0.01748    0.00211    0.00216   -0.00041
N15   3    0.508200   -0.187922    0.435717    11.00000    0.01784    0.02196 =
         0.02315    0.00161    0.00708   -0.00027
AFIX  93
H15A  2    0.550552   -0.138496    0.416379    11.00000   -1.20000
H15B  2    0.514207   -0.325423    0.462797    11.00000   -1.20000
AFIX   0
N12   3    0.371053   -0.128681    0.453553    11.00000    0.01720    0.02241 =
         0.02356    0.00302    0.00556    0.00074
AFIX  43
H12   2    0.323118   -0.036826    0.446373    11.00000   -1.20000
AFIX   0
N14   3    0.425041    0.151894    0.383533    11.00000    0.01741    0.02657 =
         0.02575    0.00408    0.00586    0.00054
AFIX  93
H14A  2    0.466762    0.203893    0.363800    11.00000   -1.20000
H14B  2    0.376276    0.237811    0.376324    11.00000   -1.20000
AFIX   0

C8    1    0.070333    1.073567    0.276286    11.00000    0.02314    0.01468 =
         0.01449   -0.00245    0.00100   -0.00265
C5    1    0.135464    0.766448    0.332317    11.00000    0.01801    0.01749 =
         0.01496   -0.00248    0.00208   -0.00356
C13   1    0.435648   -0.055788    0.424103    11.00000    0.01931    0.01743 =
         0.01861   -0.00497    0.00310   -0.00308
C10   1    0.000000    1.262491    0.250000    10.50000    0.02612    0.01508 =
         0.01860    0.00000    0.00105    0.00000
AFIX  23
H10A  2   -0.020749    1.393778    0.279841    10.50000   -1.20000
H10B  2    0.020748    1.393787    0.220160    10.50000   -1.20000
AFIX   0
H6    2    0.239571    0.811541    0.291761    11.00000    0.03419
HKLF 4




REM  2epa_0m_a.res in C2/c
REM R1 =  0.0354 for    1796 Fo > 4sig(Fo)  and  0.0406 for all    2011 data
REM    137 parameters refined using      0 restraints

END

WGHT      0.0276      2.1506

REM Highest difference peak  0.277,  deepest hole -0.213,  1-sigma level  0.045
Q1    1   0.0375  1.1563  0.2630  11.00000  0.05    0.28
Q2    1   0.0980  0.8800  0.3389  11.00000  0.05    0.26
Q3    1   0.0611  0.9831  0.2987  11.00000  0.05    0.26
Q4    1   0.1151  1.1551  0.2782  11.00000  0.05    0.22
Q5    1   0.4031 -0.1018  0.4402  11.00000  0.05    0.21
Q6    1   0.0973  1.0156  0.2580  11.00000  0.05    0.19
Q7    1   0.1638  0.8215  0.3203  11.00000  0.05    0.19
Q8    1   0.1586  0.7694  0.3087  11.00000  0.05    0.19
Q9    1   0.1713  1.2002  0.2429  11.00000  0.05    0.17
Q10   1   0.4753 -0.0792  0.4393  11.00000  0.05    0.17
Q11   1   0.4636 -0.1784  0.4176  11.00000  0.05    0.17
Q12   1   0.1454  0.6579  0.3537  11.00000  0.05    0.17
Q13   1   0.4247 -0.4961  0.5040  11.00000  0.05    0.17
Q14   1   0.4365 -0.3892  0.4925  11.00000  0.05    0.17
Q15   1   0.1176  0.5043  0.3974  11.00000  0.05    0.16
Q16   1   0.4256 -0.0059  0.3963  11.00000  0.05    0.15
Q17   1   0.4690  0.2580  0.3760  11.00000  0.05    0.15
Q18   1   0.0212  0.7870  0.3279  11.00000  0.05    0.15
Q19   1   0.0924  0.7690  0.3189  11.00000  0.05    0.14
Q20   1   0.0259  0.7862  0.3471  11.00000  0.05    0.14
;
_shelx_res_checksum              44391
_olex2_submission_special_instructions 'No special instructions were received'
