# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2031638'
loop_
_audit_author_name
_audit_author_address
'Rik Rani koner'
;IIT Mandi
India
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H26 N4 O3'
_chemical_formula_weight         370.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.3715(6)
_cell_length_b                   33.178(3)
_cell_length_c                   7.1858(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1995.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1331
_cell_measurement_theta_min      5.3180
_cell_measurement_theta_max      66.0560

_exptl_crystal_description       Triangle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.685
_shelx_estimated_absorpt_T_min   0.811
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.36324
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2470
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         6.159
_diffrn_reflns_theta_max         66.904
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.649
_diffrn_measured_fraction_theta_full 0.640
_diffrn_reflns_Laue_measured_fraction_max 0.649
_diffrn_reflns_Laue_measured_fraction_full 0.640
_diffrn_reflns_point_group_measured_fraction_max 0.510
_diffrn_reflns_point_group_measured_fraction_full 0.502
_reflns_number_total             1811
_reflns_number_gt                1541
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.338
_reflns_Friedel_fraction_max     0.311
_reflns_Friedel_fraction_full    0.306

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5.1, 2008'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 356 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(4)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1811
_refine_ls_number_parameters     223
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.1351
_refine_ls_R_factor_gt           0.1243
_refine_ls_wR_factor_ref         0.3646
_refine_ls_wR_factor_gt          0.3434
_refine_ls_goodness_of_fit_ref   1.520
_refine_ls_restrained_S_all      1.501
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O2 O -0.6129(8) -0.4485(2) -0.0386(10) 0.0441(16) Uani 1 1 d . . . . .
O1 O -0.8023(9) -0.4285(2) -0.2365(10) 0.0451(17) Uani 1 1 d . . . . .
O3 O -0.3027(10) -0.4742(3) -0.9490(12) 0.058(2) Uani 1 1 d G . . . .
N2 N 0.0124(10) -0.4477(2) -0.8797(11) 0.0403(18) Uani 1 1 d . . . . .
H2A H -0.0859 -0.4570 -0.8834 0.048 Uiso 1 1 calc R U . . .
H2B H 0.0669 -0.4446 -0.9834 0.048 Uiso 1 1 calc R U . . .
N4 N -0.5912(9) -0.3808(2) -0.4298(11) 0.0356(17) Uani 1 1 d . . . . .
H4 H -0.5901 -0.3846 -0.5510 0.043 Uiso 1 1 calc R U . . .
N3 N 0.0052(10) -0.4419(2) -0.5600(11) 0.0415(19) Uani 1 1 d . . . . .
H3 H 0.0588 -0.4341 -0.4609 0.050 Uiso 1 1 calc R U . . .
N1 N 0.2284(10) -0.4236(3) -0.7239(13) 0.046(2) Uani 1 1 d . . . . .
H1A H 0.2793 -0.4164 -0.6220 0.055 Uiso 1 1 calc R U . . .
H1B H 0.2756 -0.4214 -0.8329 0.055 Uiso 1 1 calc R U . . .
C1 C 0.0801(10) -0.4379(3) -0.7132(14) 0.0338(19) Uani 1 1 d . . . . .
C4 C -0.4274(10) -0.4422(3) -0.3952(12) 0.038(2) Uani 1 1 d . . . . .
H4A H -0.4088 -0.4647 -0.3069 0.045 Uiso 1 1 calc R U . . .
H4B H -0.4868 -0.4530 -0.5035 0.045 Uiso 1 1 calc R U . . .
C6 C -0.6630(11) -0.4301(3) -0.1845(13) 0.037(2) Uani 1 1 d . . . . .
C5 C -0.5256(11) -0.4092(3) -0.3005(12) 0.0370(19) Uani 1 1 d . . . . .
H5 H -0.4544 -0.3943 -0.2123 0.044 Uiso 1 1 calc R U . . .
C2 C -0.1520(12) -0.4569(3) -0.5221(13) 0.038(2) Uani 1 1 d . . . . .
H2C H -0.1446 -0.4779 -0.4245 0.046 Uiso 1 1 calc R U . . .
H2D H -0.1943 -0.4698 -0.6361 0.046 Uiso 1 1 calc R U . . .
C3 C -0.2676(12) -0.4250(4) -0.4594(16) 0.050(3) Uani 1 1 d . . . . .
H3A H -0.2867 -0.4061 -0.5634 0.060 Uiso 1 1 calc R U . . .
H3B H -0.2192 -0.4096 -0.3558 0.060 Uiso 1 1 calc R U . . .
C7 C -0.6597(15) -0.3450(4) -0.3437(17) 0.056(3) Uani 1 1 d . . . . .
H7A H -0.5885 -0.3354 -0.2431 0.067 Uiso 1 1 calc R U . . .
H7B H -0.7645 -0.3518 -0.2880 0.067 Uiso 1 1 calc R U . . .
C8 C -0.6823(13) -0.3096(2) -0.4997(12) 0.065(3) Uani 1 1 d G . . . .
C9 C -0.6204(13) -0.2707(3) -0.4955(14) 0.115(7) Uani 1 1 d G U . . .
H9 H -0.5538 -0.2625 -0.3954 0.138 Uiso 1 1 calc R U . . .
C10 C -0.6559(14) -0.2438(2) -0.6380(15) 0.059(3) Uani 1 1 d G . . . .
C18 C -0.7533(17) -0.2558(3) -0.7845(14) 0.116(7) Uani 1 1 d G U . . .
C19 C -0.8153(16) -0.2947(3) -0.7887(13) 0.106(6) Uani 1 1 d G . . . .
H19 H -0.8818 -0.3028 -0.8889 0.127 Uiso 1 1 calc R U . . .
C20 C -0.7798(12) -0.3216(2) -0.6463(13) 0.063(3) Uani 1 1 d G . . . .
H20 H -0.8221 -0.3481 -0.6491 0.076 Uiso 1 1 calc R U . . .
C12 C -0.6556(16) -0.1865(3) -0.8230(14) 0.065(3) Uani 1 1 d G U . . .
C13 C -0.6493(16) -0.1493(3) -0.9121(16) 0.086(4) Uani 1 1 d G U . . .
H13 H -0.5899 -0.1278 -0.8588 0.103 Uiso 1 1 calc R U . . .
C14 C -0.7300(19) -0.1436(3) -1.0791(17) 0.101(6) Uani 1 1 d G U . . .
H14 H -0.7257 -0.1182 -1.1399 0.121 Uiso 1 1 calc R U . . .
C15 C -0.8169(18) -0.1750(4) -1.1570(15) 0.093(5) Uani 1 1 d G . . . .
H15 H -0.8721 -0.1711 -1.2712 0.111 Uiso 1 1 calc R U . . .
C16 C -0.823(2) -0.2122(4) -1.0680(19) 0.110(6) Uani 1 1 d G U . . .
H16 H -0.8827 -0.2337 -1.1213 0.132 Uiso 1 1 calc R U . . .
C17 C -0.743(2) -0.2179(3) -0.9010(19) 0.148(10) Uani 1 1 d G U . . .
C11 C -0.586(3) -0.2017(6) -0.648(3) 0.091(5) Uani 1 1 d . . . . .
H11A H -0.6185 -0.1851 -0.5401 0.109 Uiso 1 1 calc R U . . .
H11B H -0.4674 -0.2025 -0.6546 0.109 Uiso 1 1 calc R U . . .
H3C H -0.3338 -0.4979 -0.9637 0.136 Uiso 1 1 d R U . . .
H3D H -0.3848 -0.4591 -0.9343 0.136 Uiso 1 1 d 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
O2 C6 1.284(12) . ?
O1 C6 1.226(12) . ?
O3 H3C 0.8366 . ?
O3 H3D 0.8568 . ?
N2 C1 1.363(13) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N4 C5 1.433(12) . ?
N4 C7 1.455(15) . ?
N4 H4 0.8800 . ?
N3 C1 1.274(14) . ?
N3 C2 1.433(13) . ?
N3 H3 0.8800 . ?
N1 C1 1.331(12) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
C4 C3 1.526(13) . ?
C4 C5 1.530(14) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 C5 1.580(14) . ?
C5 H5 1.0000 . ?
C2 C3 1.503(15) . ?
C2 H2C 0.9900 . ?
C2 H2D 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C7 C8 1.636(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.3900 . ?
C8 C20 1.3900 . ?
C9 C10 1.3900 . ?
C9 H9 0.9500 . ?
C10 C18 1.3900 . ?
C10 C11 1.52(2) . ?
C18 C19 1.3900 . ?
C18 C17 1.513(11) . ?
C19 C20 1.3900 . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C12 C13 1.3900 . ?
C12 C17 1.3900 . ?
C12 C11 1.48(2) . ?
C13 C14 1.3900 . ?
C13 H13 0.9500 . ?
C14 C15 1.3900 . ?
C14 H14 0.9500 . ?
C15 C16 1.3900 . ?
C15 H15 0.9500 . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 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
H3C O3 H3D 108.3 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C5 N4 C7 114.3(8) . . ?
C5 N4 H4 122.9 . . ?
C7 N4 H4 122.9 . . ?
C1 N3 C2 130.7(9) . . ?
C1 N3 H3 114.6 . . ?
C2 N3 H3 114.6 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
N3 C1 N1 123.1(9) . . ?
N3 C1 N2 121.9(8) . . ?
N1 C1 N2 115.0(9) . . ?
C3 C4 C5 109.7(9) . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
O1 C6 O2 125.4(9) . . ?
O1 C6 C5 120.8(8) . . ?
O2 C6 C5 113.7(8) . . ?
N4 C5 C4 112.9(7) . . ?
N4 C5 C6 110.6(8) . . ?
C4 C5 C6 108.1(7) . . ?
N4 C5 H5 108.4 . . ?
C4 C5 H5 108.4 . . ?
C6 C5 H5 108.4 . . ?
N3 C2 C3 113.8(9) . . ?
N3 C2 H2C 108.8 . . ?
C3 C2 H2C 108.8 . . ?
N3 C2 H2D 108.8 . . ?
C3 C2 H2D 108.8 . . ?
H2C C2 H2D 107.7 . . ?
C2 C3 C4 113.1(10) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
N4 C7 C8 109.9(9) . . ?
N4 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
N4 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C20 120.0 . . ?
C9 C8 C7 127.5(7) . . ?
C20 C8 C7 112.5(7) . . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C18 C10 C9 120.0 . . ?
C18 C10 C11 117.0(10) . . ?
C9 C10 C11 122.9(10) . . ?
C10 C18 C19 120.0 . . ?
C10 C18 C17 98.4(9) . . ?
C19 C18 C17 141.4(9) . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C8 120.0 . . ?
C19 C20 H20 120.0 . . ?
C8 C20 H20 120.0 . . ?
C13 C12 C17 120.0 . . ?
C13 C12 C11 132.9(11) . . ?
C17 C12 C11 107.1(11) . . ?
C14 C13 C12 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 120.0 . . ?
C16 C17 C18 124.2(9) . . ?
C12 C17 C18 115.6(9) . . ?
C12 C11 C10 101.7(15) . . ?
C12 C11 H11A 111.4 . . ?
C10 C11 H11A 111.4 . . ?
C12 C11 H11B 111.4 . . ?
C10 C11 H11B 111.4 . . ?
H11A C11 H11B 109.3 . . ?

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
C2 N3 C1 N1 -179.2(9) . . . . ?
C2 N3 C1 N2 1.5(15) . . . . ?
C7 N4 C5 C4 -169.2(8) . . . . ?
C7 N4 C5 C6 69.5(10) . . . . ?
C3 C4 C5 N4 74.1(10) . . . . ?
C3 C4 C5 C6 -163.2(7) . . . . ?
O1 C6 C5 N4 16.5(12) . . . . ?
O2 C6 C5 N4 -164.7(8) . . . . ?
O1 C6 C5 C4 -107.6(10) . . . . ?
O2 C6 C5 C4 71.3(10) . . . . ?
C1 N3 C2 C3 -110.2(11) . . . . ?
N3 C2 C3 C4 -172.4(8) . . . . ?
C5 C4 C3 C2 169.5(8) . . . . ?
C5 N4 C7 C8 163.5(8) . . . . ?
N4 C7 C8 C9 -123.4(8) . . . . ?
N4 C7 C8 C20 58.5(11) . . . . ?
C20 C8 C9 C10 0.0 . . . . ?
C7 C8 C9 C10 -177.9(11) . . . . ?
C8 C9 C10 C18 0.0 . . . . ?
C8 C9 C10 C11 -176.6(13) . . . . ?
C9 C10 C18 C19 0.0 . . . . ?
C11 C10 C18 C19 176.8(12) . . . . ?
C9 C10 C18 C17 -176.0(11) . . . . ?
C11 C10 C18 C17 0.8(14) . . . . ?
C10 C18 C19 C20 0.0 . . . . ?
C17 C18 C19 C20 173.7(18) . . . . ?
C18 C19 C20 C8 0.0 . . . . ?
C9 C8 C20 C19 0.0 . . . . ?
C7 C8 C20 C19 178.2(10) . . . . ?
C17 C12 C13 C14 0.0 . . . . ?
C11 C12 C13 C14 -179.6(16) . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C12 0.0 . . . . ?
C15 C16 C17 C18 174.4(16) . . . . ?
C13 C12 C17 C16 0.0 . . . . ?
C11 C12 C17 C16 179.7(13) . . . . ?
C13 C12 C17 C18 -174.9(14) . . . . ?
C11 C12 C17 C18 4.9(14) . . . . ?
C10 C18 C17 C16 -178.1(8) . . . . ?
C19 C18 C17 C16 7.4(19) . . . . ?
C10 C18 C17 C12 -3.5(12) . . . . ?
C19 C18 C17 C12 -178.0(9) . . . . ?
C13 C12 C11 C10 175.9(11) . . . . ?
C17 C12 C11 C10 -3.8(14) . . . . ?
C18 C10 C11 C12 1.8(16) . . . . ?
C9 C10 C11 C12 178.5(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O3 0.88 1.96 2.825(12) 167.4 .
N2 H2B O1 0.88 2.19 3.064(10) 172.5 1_654
N4 H4 N1 0.88 2.35 2.961(11) 126.6 1_455
N1 H1A N4 0.88 2.12 2.961(11) 160.4 1_655
N1 H1B O2 0.88 1.97 2.750(12) 147.4 1_654
C2 H2D O3 0.99 2.43 3.366(13) 157.7 .
C7 H7B O1 0.99 2.59 3.112(15) 112.8 .
O3 H3C O2 0.84 1.91 2.736(12) 170.0 2_444
O3 H3D O2 0.86 2.08 2.808(11) 142.3 1_554
N2 H2A O3 0.88 1.96 2.825(12) 167.4 .
N2 H2B O1 0.88 2.19 3.064(10) 172.5 1_654
N4 H4 N1 0.88 2.35 2.961(11) 126.6 1_455
N1 H1A N4 0.88 2.12 2.961(11) 160.4 1_655
N1 H1B O2 0.88 1.97 2.750(12) 147.4 1_654
C2 H2D O3 0.99 2.43 3.366(13) 157.7 .
C7 H7B O1 0.99 2.59 3.112(15) 112.8 .
O3 H3C O2 0.84 1.91 2.736(12) 170.0 2_444
O3 H3D O2 0.86 2.08 2.808(11) 142.3 1_554

_refine_diff_density_max         0.608
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.092

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_fa_sma_rt_cu
_database_code_depnum_ccdc_archive 'CCDC 2031639'
loop_
_audit_author_name
_audit_author_address
'Rik Rani koner'
;IIT Mandi
India
;
_audit_update_record             
;
2020-11-30 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;
_audit_creation_date             2020-11-30
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C8 H7 O3, C20 H25 N4 O2'
_chemical_formula_sum            'C28 H32 N4 O5'
_chemical_formula_weight         504.58
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C56 H64 N8 O10'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   10.8104(5)
_cell_length_b                   5.7783(3)
_cell_length_c                   21.3807(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.903(5)
_cell_angle_gamma                90.00
_cell_volume                     1334.82(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2088
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.9520
_cell_measurement_theta_min      4.1370
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.614
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 0 12 0.0479
-7 0 5 0.0315
2 0 -14 0.0426
-2 -2 10 0.1328
0 4 1 0.1907
0 -4 -1 0.1957
1 -2 -12 0.1018
6 0 -7 0.0487
-1 0 14 0.0346
7 0 1 0.0545
-3 0 -12 0.0479
-6 0 -7 0.0396

_exptl_crystal_size_max          0.393
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.079
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.0000 0.0000 11.9998 -0.7555 -0.1779 -0.5945
-7.0000 0.0001 4.9996 -0.5478 0.3615 0.8191
2.0000 -0.0001 -13.9996 1.0368 -0.0829 -0.0177
-2.0000 -2.0000 9.9998 -0.7201 0.5847 -0.1077
0.0000 4.0000 0.9997 -0.1432 -0.9923 0.3712
-0.0000 -4.0000 -0.9997 0.1432 0.9923 -0.3712
1.0000 -2.0001 -11.9995 0.9051 0.4620 -0.1170
6.0000 -0.0001 -6.9996 0.6596 -0.3054 -0.6554
-1.0000 0.0001 13.9996 -1.0085 0.0301 -0.1116
7.0000 -0.0000 1.0003 0.1277 -0.3712 -0.9224
-3.0000 -0.0000 -11.9998 0.7555 0.1779 0.5945
-6.0000 0.0000 -7.0001 0.3207 0.3282 0.8963

_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4483
_diffrn_reflns_theta_full        66.86
_diffrn_reflns_theta_max         66.86
_diffrn_reflns_theta_min         7.94
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00  52.00   1.00    1.00    --   25.69 -57.00-180.00  103
  2  ω     57.00 116.00   1.00    1.00    --   25.69 178.00  30.00   59
  3  ω     82.00 119.00   1.00    1.00    --   25.69 178.00-180.00   37
  4  ω     32.00 104.00   1.00    2.00    --   66.85  63.00-180.00   72
  5  ω      4.00 109.00   1.00    2.00    --   66.85 -50.00-120.00  105
  6  ω    105.00 150.00   1.00    2.00    --   66.85 111.00 -30.00   45
  7  ω     43.00 112.00   1.00    2.00    --   66.85-111.00  30.00   69
  8  ω     12.00  84.00   1.00    2.00    --   66.85-111.00 -90.00   72
  9  ω    141.00 175.00   1.00    7.00    --  108.00  54.00 -30.00   34
 10  ω    104.00 177.00   1.00    7.00    --  108.00 104.00-150.00   73
 11  ω    142.00 175.00   1.00    7.00    --  108.00  65.00  30.00   33
 12  ω     95.00 128.00   1.00    7.00    --  108.00  54.00 -30.00   33
 13  ω    109.00 169.00   1.00    7.00    --  108.00 138.00 -30.00   60
 14  ω    109.00 176.00   1.00    7.00    --  108.00  43.00  90.00   67
 15  ω     42.00  99.00   1.00    7.00    --  108.00-104.00  60.00   57
 16  ω     55.00  80.00   1.00    7.00    --  108.00-104.00 150.00   25
 17  ω     24.00  52.00   1.00    7.00    --  108.00-104.00 150.00   28
 18  ω     64.00  91.00   1.00    7.00    --  108.00  43.00  90.00   27
 19  ω    101.00 157.00   1.00    7.00    --  108.00 104.00 150.00   56
 20  ω     95.00 135.00   1.00    7.00    --  108.00  65.00  30.00   40
 21  ω    108.00 175.00   1.00    7.00    --  108.00 104.00 -60.00   67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0282486000
_diffrn_orient_matrix_UB_12      -0.0182897000
_diffrn_orient_matrix_UB_13      -0.0700233000
_diffrn_orient_matrix_UB_21      -0.0528035000
_diffrn_orient_matrix_UB_22      -0.2476644000
_diffrn_orient_matrix_UB_23      -0.0016239000
_diffrn_orient_matrix_UB_31      -0.1293091000
_diffrn_orient_matrix_UB_32      0.0971036000
_diffrn_orient_matrix_UB_33      -0.0172115000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2576
_reflns_number_total             2860
_reflns_odcompleteness_completeness 98.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         2860
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0396P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0815
_refine_special_details          
;Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.,SQUEEZE
;
_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
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 N4(H4A,H4B), C7(H7A,H7B), C3(H3A,H3B), C2(H2C,H2D), C11(H11A,H11B), C4(H4C,H4D)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), N3(H3), C20(H20), C19(H19), C28(H28), C16(H16), C27(H27), C13(H13),
 C26(H26), C24(H24), C14(H14), C15(H15), C25(H25)
2.d X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N1(H1A,H1B)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O3 O -0.10603(14) -0.3643(3) -0.07700(8) 0.0485(4) Uani 1 d . . .
N4 N -0.52587(15) 0.2502(3) 0.22515(8) 0.0330(4) Uani 1 d . . .
H4A H -0.4942 0.1065 0.2283 0.040 Uiso 1 calc . . R
H4B H -0.5795 0.2518 0.1921 0.040 Uiso 1 calc . . R
N2 N -0.2758(2) 0.1247(5) -0.05283(10) 0.0538(5) Uani 1 d . . .
H2A H -0.2639 0.0084 -0.0770 0.065 Uiso 1 calc . . R
H2B H -0.3327 0.2239 -0.0623 0.065 Uiso 1 calc . . R
O4 O -0.29030(15) -0.3097(4) -0.12346(8) 0.0485(4) Uani 1 d . . .
O1 O -0.42636(17) 0.8173(3) 0.23453(9) 0.0501(4) Uani 1 d . . .
O2 O -0.5627(2) 0.6781(3) 0.16406(10) 0.0610(5) Uani 1 d . . .
O5 O -0.23973(17) -0.6147(3) -0.21641(9) 0.0520(4) Uani 1 d . . .
H5A H -0.2999 -0.6482 -0.1959 0.078 Uiso 1 calc . . GR
C9 C -0.4252(2) 0.1711(4) 0.35961(10) 0.0379(4) Uani 1 d . . .
H9 H -0.4149 0.0371 0.3363 0.045 Uiso 1 calc . . R
C21 C -0.18354(18) -0.3940(4) -0.12096(10) 0.0366(4) Uani 1 d . . .
N1 N -0.1199(2) -0.0014(5) 0.01291(11) 0.0532(5) Uani 1 d . . .
H1A H -0.1085 -0.1172 -0.0115 0.064 Uiso 1 calc . . R
H1B H -0.0745 0.0145 0.0464 0.064 Uiso 1 calc . . R
C7 C -0.59625(18) 0.3006(4) 0.28351(10) 0.0388(5) Uani 1 d . . .
H7A H -0.6452 0.4395 0.2766 0.047 Uiso 1 calc . . R
H7B H -0.6530 0.1739 0.2906 0.047 Uiso 1 calc . . R
N3 N -0.22634(19) 0.3338(4) 0.03488(9) 0.0465(5) Uani 1 d . . .
H3 H -0.2827 0.4296 0.0222 0.056 Uiso 1 calc . . R
C5 C -0.42357(18) 0.4143(4) 0.21280(9) 0.0308(4) Uani 1 d . . .
H5 H -0.3654 0.4151 0.2489 0.037 Uiso 1 calc . . R
C1 C -0.2065(2) 0.1510(5) -0.00102(11) 0.0420(5) Uani 1 d . . .
C18 C -0.3703(2) 0.4095(4) 0.44947(10) 0.0414(5) Uani 1 d . . .
C8 C -0.51496(19) 0.3334(4) 0.34138(10) 0.0372(4) Uani 1 d . . .
C6 C -0.4757(2) 0.6585(4) 0.20321(10) 0.0362(4) Uani 1 d . . .
C17 C -0.2794(2) 0.4075(5) 0.50227(11) 0.0489(6) Uani 1 d . . .
C3 C -0.2485(2) 0.4921(4) 0.14004(11) 0.0412(5) Uani 1 d . . .
H3A H -0.2812 0.6359 0.1229 0.049 Uiso 1 calc . . R
H3B H -0.2022 0.5283 0.1785 0.049 Uiso 1 calc . . R
C22 C -0.1416(2) -0.5434(4) -0.17581(11) 0.0394(5) Uani 1 d . . .
H22 H -0.0992 -0.6810 -0.1590 0.047 Uiso 1 calc . . R
C10 C -0.3516(2) 0.2116(4) 0.41288(10) 0.0395(5) Uani 1 d . . .
C20 C -0.5320(2) 0.5308(4) 0.37795(11) 0.0436(5) Uani 1 d . . .
H20 H -0.5914 0.6390 0.3654 0.052 Uiso 1 calc . . R
C23 C -0.05227(19) -0.4082(4) -0.21500(10) 0.0388(5) Uani 1 d . . .
C19 C -0.4618(2) 0.5684(5) 0.43264(12) 0.0486(6) Uani 1 d . . .
H19 H -0.4758 0.6974 0.4574 0.058 Uiso 1 calc . . R
C2 C -0.1612(2) 0.3859(5) 0.09365(12) 0.0471(5) Uani 1 d . . .
H2C H -0.0941 0.4929 0.0862 0.057 Uiso 1 calc . . R
H2D H -0.1257 0.2449 0.1111 0.057 Uiso 1 calc . . R
C28 C -0.0842(2) -0.1905(5) -0.23685(12) 0.0471(5) Uani 1 d . . .
H28 H -0.1569 -0.1217 -0.2241 0.057 Uiso 1 calc . . R
C16 C -0.2606(3) 0.5657(7) 0.55111(12) 0.0664(8) Uani 1 d . . .
H16 H -0.3106 0.6957 0.5549 0.080 Uiso 1 calc . . R
C11 C -0.2442(2) 0.0726(5) 0.43975(13) 0.0519(6) Uani 1 d . . .
H11A H -0.1782 0.0611 0.4103 0.062 Uiso 1 calc . . R
H11B H -0.2701 -0.0818 0.4514 0.062 Uiso 1 calc . . R
C27 C -0.0086(3) -0.0733(6) -0.27764(15) 0.0664(8) Uani 1 d . . .
H27 H -0.0316 0.0722 -0.2926 0.080 Uiso 1 calc . . R
C12 C -0.2043(3) 0.2126(5) 0.49660(12) 0.0513(6) Uani 1 d . . .
C13 C -0.1066(3) 0.1717(7) 0.53945(15) 0.0690(8) Uani 1 d . . .
H13 H -0.0559 0.0426 0.5358 0.083 Uiso 1 calc . . R
C26 C 0.1002(3) -0.1726(8) -0.29596(15) 0.0737(10) Uani 1 d . . .
H26 H 0.1499 -0.0964 -0.3241 0.088 Uiso 1 calc . . R
C24 C 0.0590(2) -0.5032(5) -0.23245(13) 0.0535(6) Uani 1 d . . .
H24 H 0.0833 -0.6477 -0.2173 0.064 Uiso 1 calc . . R
C14 C -0.0872(4) 0.3297(8) 0.58782(16) 0.0790(11) Uani 1 d . . .
H14 H -0.0217 0.3070 0.6165 0.095 Uiso 1 calc . . R
C15 C -0.1631(4) 0.5194(8) 0.59415(14) 0.0785(11) Uani 1 d . . .
H15 H -0.1492 0.6191 0.6278 0.094 Uiso 1 calc . . R
C25 C 0.1345(3) -0.3823(8) -0.27269(16) 0.0710(10) Uani 1 d . . .
H25 H 0.2096 -0.4464 -0.2838 0.085 Uiso 1 calc . . R
C4 C -0.3557(2) 0.3330(4) 0.15506(10) 0.0374(4) Uani 1 d . . .
H4C H -0.3244 0.1775 0.1623 0.045 Uiso 1 calc . . R
H4D H -0.4135 0.3276 0.1194 0.045 Uiso 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
O3 C21 1.250(3) . ?
N4 C7 1.511(3) . ?
N4 C5 1.487(3) . ?
N2 C1 1.325(3) . ?
O4 C21 1.252(3) . ?
O1 C6 1.245(3) . ?
O2 C6 1.243(3) . ?
O5 C22 1.410(3) . ?
C9 C8 1.395(3) . ?
C9 C10 1.387(3) . ?
C21 C22 1.537(3) . ?
N1 C1 1.312(4) . ?
C7 C8 1.506(3) . ?
N3 C1 1.327(3) . ?
N3 C2 1.452(3) . ?
C5 C6 1.531(3) . ?
C5 C4 1.531(3) . ?
C18 C17 1.472(3) . ?
C18 C10 1.404(3) . ?
C18 C19 1.388(4) . ?
C8 C20 1.398(3) . ?
C17 C16 1.397(4) . ?
C17 C12 1.396(4) . ?
C3 C2 1.520(3) . ?
C3 C4 1.522(3) . ?
C22 C23 1.516(3) . ?
C10 C11 1.509(3) . ?
C20 C19 1.390(4) . ?
C23 C28 1.381(4) . ?
C23 C24 1.384(4) . ?
C28 C27 1.391(4) . ?
C16 C15 1.402(5) . ?
C11 C12 1.511(4) . ?
C27 C26 1.378(6) . ?
C12 C13 1.395(4) . ?
C13 C14 1.390(6) . ?
C26 C25 1.357(6) . ?
C24 C25 1.394(5) . ?
C14 C15 1.378(7) . ?

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 C7 114.93(16) . . ?
C10 C9 C8 119.4(2) . . ?
O3 C21 O4 124.9(2) . . ?
O3 C21 C22 116.31(18) . . ?
O4 C21 C22 118.75(18) . . ?
C8 C7 N4 114.00(16) . . ?
C1 N3 C2 125.6(2) . . ?
N4 C5 C6 109.82(15) . . ?
N4 C5 C4 109.07(16) . . ?
C4 C5 C6 111.04(17) . . ?
N2 C1 N3 118.5(2) . . ?
N1 C1 N2 119.5(2) . . ?
N1 C1 N3 122.0(2) . . ?
C10 C18 C17 108.5(2) . . ?
C19 C18 C17 131.0(2) . . ?
C19 C18 C10 120.6(2) . . ?
C9 C8 C7 121.8(2) . . ?
C9 C8 C20 119.7(2) . . ?
C20 C8 C7 118.6(2) . . ?
O1 C6 C5 117.26(18) . . ?
O2 C6 O1 126.6(2) . . ?
O2 C6 C5 116.16(19) . . ?
C16 C17 C18 130.1(3) . . ?
C12 C17 C18 108.4(2) . . ?
C12 C17 C16 121.5(3) . . ?
C2 C3 C4 112.8(2) . . ?
O5 C22 C21 113.50(18) . . ?
O5 C22 C23 106.89(19) . . ?
C23 C22 C21 109.99(18) . . ?
C9 C10 C18 120.4(2) . . ?
C9 C10 C11 129.5(2) . . ?
C18 C10 C11 110.1(2) . . ?
C19 C20 C8 121.3(2) . . ?
C28 C23 C22 120.0(2) . . ?
C28 C23 C24 118.6(2) . . ?
C24 C23 C22 121.3(2) . . ?
C18 C19 C20 118.6(2) . . ?
N3 C2 C3 110.77(19) . . ?
C23 C28 C27 120.7(3) . . ?
C17 C16 C15 116.9(4) . . ?
C10 C11 C12 102.5(2) . . ?
C26 C27 C28 120.0(3) . . ?
C17 C12 C11 110.5(2) . . ?
C13 C12 C17 120.6(3) . . ?
C13 C12 C11 128.9(3) . . ?
C14 C13 C12 118.0(4) . . ?
C25 C26 C27 119.5(3) . . ?
C23 C24 C25 120.0(3) . . ?
C15 C14 C13 121.3(3) . . ?
C14 C15 C16 121.6(3) . . ?
C26 C25 C24 121.1(3) . . ?
C3 C4 C5 111.94(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4A O1 0.90 1.83 2.728(2) 178.7 1_545
O5 H5A O2 0.82 1.93 2.722(3) 160.5 2_435
N1 H1A O3 0.86 2.00 2.852(3) 170.2 .
N1 H1B O3 0.86 2.15 2.872(3) 140.7 2

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 -0.557 0.000 71.1 20.9 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.635
####################################################################### 
# 
# 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_fda_rma_rt_cu
_database_code_depnum_ccdc_archive 'CCDC 2047297'
loop_
_audit_author_name
_audit_author_address
'Rik Rani koner'
;IIT Mandi
India
;
_audit_update_record             
;
2020-11-30 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;
_audit_creation_date             2020-11-30
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C8 H7 O3, C20 H25 N4 O2'
_chemical_formula_sum            'C28 H32 N4 O5'
_chemical_formula_weight         504.58
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C56 H68 N8 O12'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   10.8308(8)
_cell_length_b                   5.7790(4)
_cell_length_c                   21.3692(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.933(7)
_cell_angle_gamma                90.00
_cell_volume                     1336.77(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1317
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.6580
_cell_measurement_theta_min      4.0700
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.839
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 1 6 0.0656
1 4 2 0.1137
0 0 -14 0.0396
0 0 14 0.0396
-6 -1 -6 0.0572
-6 1 -6 0.0639
6 0 -9 0.0329
-6 0 8 0.0350
6 0 5 0.0187
-2 -4 -1 0.0902

_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.068
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.9980 1.0016 5.9998 0.2018 0.9558 -0.0976
1.0040 4.0049 2.0101 0.0087 0.1222 -1.0796
0.0030 0.0032 -13.9896 -0.9815 -0.2089 0.1077
-0.0030 -0.0032 13.9896 0.9815 0.2089 -0.1077
-5.9978 -0.9984 -5.9972 -0.5588 0.6632 0.5097
-5.9955 1.0044 -5.9913 -0.6395 0.7768 -0.0053
5.9998 0.0005 -8.9946 -0.4525 -0.9438 -0.1368
-5.9996 -0.0002 7.9953 0.3824 0.9289 0.1445
5.9969 -0.0027 4.9950 0.5290 -0.7349 -0.2445
-2.0038 -4.0048 -1.0106 0.0317 0.0277 1.1063

_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4185
_diffrn_reflns_theta_full        66.83
_diffrn_reflns_theta_max         66.83
_diffrn_reflns_theta_min         6.22
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  60.00   1.00    1.00    --   25.57 -57.00  30.00  102
  2  ω    -27.00  64.00   1.00    1.00    --   25.57 -57.00 120.00   91
  3  ω    -13.00 111.00   1.00   10.00    --   66.78 -45.00  60.00  124
  4  ω    104.00 144.00   1.00   10.00    --   66.78 121.00  53.00   40
  5  ω      5.00  98.00   1.00   10.00    --   66.78 -61.00 -60.00   93
  6  ω     68.00 127.00   1.00   10.00    --   66.78  61.00-150.00   59
  7  ω     93.00 137.00   1.00   35.00    --  108.00 -21.00 -60.00   44
  8  ω     53.00  90.00   1.00   35.00    --  108.00-104.00 -30.00   37
  9  ω     52.00  87.00   1.00   35.00    --  108.00 -54.00 -90.00   35
 10  ω     52.00 177.00   1.00   35.00    --  108.00  32.00-180.00  125
 11  ω     28.00 111.00   1.00   35.00    --  108.00-104.00  30.00   83
 12  ω     38.00  64.00   1.00   35.00    --  108.00 -21.00 -60.00   26
 13  ω    130.00 172.00   1.00   35.00    --  108.00  54.00 120.00   42
 14  ω     27.00 112.00   1.00   35.00    --  108.00 -32.00-150.00   85
 15  ω     68.00  96.00   1.00   35.00    --  108.00  54.00 120.00   28
 16  ω    105.00 147.00   1.00   35.00    --  108.00 -54.00 -90.00   42
 17  ω    119.00 157.00   1.00   35.00    --  108.00 104.00  30.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0297642000
_diffrn_orient_matrix_UB_12      -0.0405001000
_diffrn_orient_matrix_UB_13      0.0701586000
_diffrn_orient_matrix_UB_21      -0.1349472000
_diffrn_orient_matrix_UB_22      0.0568509000
_diffrn_orient_matrix_UB_23      0.0149157000
_diffrn_orient_matrix_UB_31      -0.0344205000
_diffrn_orient_matrix_UB_32      -0.2570477000
_diffrn_orient_matrix_UB_33      -0.0077643000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2442
_reflns_number_total             2815
_reflns_odcompleteness_completeness 98.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         2815
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0393P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0921
_refine_special_details          
;Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.,SQUEEZE
;
_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
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 N4(H4A,H4B), C7(H7A,H7B), C4(H4C,H4D), C3(H3A,H3B), C11(H11A,H11B), C2(H2C,H2D)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C9(H9), C24(H24), C19(H19), C20(H20), C28(H28), C26(H26), C27(H27),
 C13(H13), C15(H15), C25(H25), C16(H16), C14(H14)
2.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O4 O 0.10581(18) 0.0780(4) 0.07685(9) 0.0486(5) Uani 1 d . . .
O1 O 0.5739(2) 0.3967(3) 0.23460(11) 0.0506(5) Uani 1 d . . .
O3 O 0.29048(18) 0.0229(4) 0.12338(9) 0.0496(5) Uani 1 d . . .
O5 O 0.2394(2) 0.3284(4) 0.21638(10) 0.0529(5) Uani 1 d . . .
H5A H 0.2952 0.3820 0.1958 0.079 Uiso 1 calc . . GR
N4 N 0.47370(19) 0.9638(4) 0.22536(9) 0.0338(4) Uani 1 d . . .
H4A H 0.4200 0.9631 0.1923 0.041 Uiso 1 calc . . R
H4B H 0.5056 1.1073 0.2286 0.041 Uiso 1 calc . . R
O2 O 0.4371(2) 0.5352(4) 0.16421(11) 0.0623(6) Uani 1 d . . .
N3 N 0.7731(2) 0.8805(5) 0.03495(11) 0.0470(6) Uani 1 d . . .
H3 H 0.7161 0.7856 0.0226 0.056 Uiso 1 calc . . R
N1 N 0.8803(2) 1.2155(5) 0.01282(13) 0.0545(6) Uani 1 d . . .
H1A H 0.9255 1.2004 0.0464 0.065 Uiso 1 calc . . R
H1B H 0.8915 1.3311 -0.0117 0.065 Uiso 1 calc . . R
N2 N 0.7235(2) 1.0895(6) -0.05296(12) 0.0540(6) Uani 1 d . . .
H2A H 0.7348 1.2071 -0.0768 0.065 Uiso 1 calc . . R
H2B H 0.6669 0.9903 -0.0626 0.065 Uiso 1 calc . . R
C23 C 0.0524(2) 0.1223(5) 0.21451(12) 0.0407(6) Uani 1 d . . .
C6 C 0.5241(2) 0.5550(5) 0.20341(12) 0.0367(5) Uani 1 d . . .
C21 C 0.1840(2) 0.1068(5) 0.12129(12) 0.0381(6) Uani 1 d . . .
C8 C 0.4856(2) 0.8810(5) 0.34122(12) 0.0365(5) Uani 1 d . . .
C18 C 0.6293(3) 0.8047(5) 0.44914(13) 0.0426(6) Uani 1 d . . .
C9 C 0.5743(2) 1.0422(5) 0.35972(12) 0.0384(5) Uani 1 d . . .
H9 H 0.5842 1.1769 0.3366 0.046 Uiso 1 calc . . R
C1 C 0.7938(2) 1.0611(6) -0.00116(13) 0.0411(6) Uani 1 d . . .
C7 C 0.4035(2) 0.9137(5) 0.28349(12) 0.0391(6) Uani 1 d . . .
H7A H 0.3546 0.7748 0.2767 0.047 Uiso 1 calc . . R
H7B H 0.3470 1.0405 0.2906 0.047 Uiso 1 calc . . R
C5 C 0.5758(2) 0.7994(4) 0.21261(11) 0.0318(5) Uani 1 d . . .
H5 H 0.6339 0.7985 0.2488 0.038 Uiso 1 calc . . R
C4 C 0.6443(2) 0.8802(5) 0.15522(12) 0.0385(5) Uani 1 d . . .
H4C H 0.5868 0.8859 0.1194 0.046 Uiso 1 calc . . R
H4D H 0.6754 1.0355 0.1626 0.046 Uiso 1 calc . . R
C3 C 0.7512(3) 0.7222(5) 0.14025(13) 0.0430(6) Uani 1 d . . .
H3A H 0.7186 0.5788 0.1228 0.052 Uiso 1 calc . . R
H3B H 0.7968 0.6851 0.1788 0.052 Uiso 1 calc . . R
C22 C 0.1414(3) 0.2554(5) 0.17553(13) 0.0407(6) Uani 1 d . . .
H22 H 0.0991 0.3925 0.1584 0.049 Uiso 1 calc . . R
C24 C 0.0837(3) -0.0968(6) 0.23647(14) 0.0475(6) Uani 1 d . . .
H24 H 0.1558 -0.1669 0.2235 0.057 Uiso 1 calc . . R
C17 C 0.7213(3) 0.8065(6) 0.50223(13) 0.0491(7) Uani 1 d . . .
C10 C 0.6483(3) 1.0016(5) 0.41292(12) 0.0394(6) Uani 1 d . . .
C19 C 0.5382(3) 0.6469(6) 0.43264(14) 0.0480(7) Uani 1 d . . .
H19 H 0.5242 0.5186 0.4577 0.058 Uiso 1 calc . . R
C11 C 0.7556(3) 1.1409(6) 0.43983(15) 0.0511(7) Uani 1 d . . .
H11A H 0.7296 1.2950 0.4517 0.061 Uiso 1 calc . . R
H11B H 0.8213 1.1532 0.4103 0.061 Uiso 1 calc . . R
C12 C 0.7961(3) 1.0007(6) 0.49659(14) 0.0519(8) Uani 1 d . . .
C20 C 0.4675(3) 0.6831(5) 0.37790(14) 0.0445(6) Uani 1 d . . .
H20 H 0.4078 0.5753 0.3655 0.053 Uiso 1 calc . . R
C2 C 0.8390(3) 0.8285(6) 0.09429(14) 0.0482(7) Uani 1 d . . .
H2C H 0.8742 0.9696 0.1118 0.058 Uiso 1 calc . . R
H2D H 0.9061 0.7216 0.0869 0.058 Uiso 1 calc . . R
C28 C -0.0593(3) 0.2166(7) 0.23254(15) 0.0540(8) Uani 1 d . . .
H28 H -0.0838 0.3610 0.2174 0.065 Uiso 1 calc . . R
C26 C -0.0998(4) -0.1134(10) 0.29562(17) 0.0739(12) Uani 1 d . . .
H26 H -0.1494 -0.1907 0.3235 0.089 Uiso 1 calc . . R
C27 C -0.1343(3) 0.0977(9) 0.27272(18) 0.0694(11) Uani 1 d . . .
H27 H -0.2088 0.1625 0.2842 0.083 Uiso 1 calc . . R
C13 C 0.8930(4) 1.0421(8) 0.53932(17) 0.0689(10) Uani 1 d . . .
H13 H 0.9434 1.1712 0.5355 0.083 Uiso 1 calc . . R
C15 C 0.8364(5) 0.6960(10) 0.59381(17) 0.0828(14) Uani 1 d . . .
H15 H 0.8503 0.5960 0.6274 0.099 Uiso 1 calc . . R
C25 C 0.0089(4) -0.2117(8) 0.27731(18) 0.0676(10) Uani 1 d . . .
H25 H 0.0322 -0.3566 0.2925 0.081 Uiso 1 calc . . R
C16 C 0.7395(4) 0.6492(8) 0.55117(15) 0.0687(10) Uani 1 d . . .
H16 H 0.6895 0.5195 0.5551 0.082 Uiso 1 calc . . R
C14 C 0.9125(5) 0.8862(10) 0.58786(18) 0.0794(13) Uani 1 d . . .
H14 H 0.9775 0.9096 0.6167 0.095 Uiso 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
O4 C21 1.262(3) . ?
O1 C6 1.244(3) . ?
O3 C21 1.250(3) . ?
O5 H5A 0.8200 . ?
O5 C22 1.416(3) . ?
N4 H4A 0.9000 . ?
N4 H4B 0.9000 . ?
N4 C7 1.506(3) . ?
N4 C5 1.490(3) . ?
O2 C6 1.245(3) . ?
N3 H3 0.8600 . ?
N3 C1 1.322(4) . ?
N3 C2 1.466(4) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.321(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C1 1.332(4) . ?
C23 C22 1.506(4) . ?
C23 C24 1.389(4) . ?
C23 C28 1.393(4) . ?
C6 C5 1.529(3) . ?
C21 C22 1.527(4) . ?
C8 C9 1.387(4) . ?
C8 C7 1.508(3) . ?
C8 C20 1.404(4) . ?
C18 C17 1.484(4) . ?
C18 C10 1.396(4) . ?
C18 C19 1.381(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.389(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 H5 0.9800 . ?
C5 C4 1.527(4) . ?
C4 H4C 0.9700 . ?
C4 H4D 0.9700 . ?
C4 C3 1.517(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.520(4) . ?
C22 H22 0.9800 . ?
C24 H24 0.9300 . ?
C24 C25 1.380(5) . ?
C17 C12 1.392(5) . ?
C17 C16 1.395(5) . ?
C10 C11 1.511(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.392(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.512(4) . ?
C12 C13 1.388(5) . ?
C20 H20 0.9300 . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C28 H28 0.9300 . ?
C28 C27 1.384(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.362(7) . ?
C26 C25 1.376(7) . ?
C27 H27 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.385(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.393(7) . ?
C15 C14 1.383(8) . ?
C25 H25 0.9300 . ?
C16 H16 0.9300 . ?
C14 H14 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
C22 O5 H5A 109.5 . . ?
H4A N4 H4B 107.5 . . ?
C7 N4 H4A 108.5 . . ?
C7 N4 H4B 108.5 . . ?
C5 N4 H4A 108.5 . . ?
C5 N4 H4B 108.5 . . ?
C5 N4 C7 115.24(19) . . ?
C1 N3 H3 117.3 . . ?
C1 N3 C2 125.4(3) . . ?
C2 N3 H3 117.3 . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
C24 C23 C22 119.9(3) . . ?
C24 C23 C28 117.9(3) . . ?
C28 C23 C22 122.1(3) . . ?
O1 C6 O2 126.7(3) . . ?
O1 C6 C5 117.4(2) . . ?
O2 C6 C5 115.9(2) . . ?
O4 C21 C22 115.6(2) . . ?
O3 C21 O4 124.8(3) . . ?
O3 C21 C22 119.6(2) . . ?
C9 C8 C7 122.2(3) . . ?
C9 C8 C20 119.8(2) . . ?
C20 C8 C7 118.0(3) . . ?
C10 C18 C17 108.1(3) . . ?
C19 C18 C17 131.0(3) . . ?
C19 C18 C10 121.0(3) . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.7(3) . . ?
C10 C9 H9 120.2 . . ?
N3 C1 N2 118.6(3) . . ?
N1 C1 N3 122.3(3) . . ?
N1 C1 N2 119.1(3) . . ?
N4 C7 C8 113.5(2) . . ?
N4 C7 H7A 108.9 . . ?
N4 C7 H7B 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
N4 C5 C6 109.98(19) . . ?
N4 C5 H5 108.6 . . ?
N4 C5 C4 109.59(19) . . ?
C6 C5 H5 108.6 . . ?
C4 C5 C6 111.4(2) . . ?
C4 C5 H5 108.6 . . ?
C5 C4 H4C 109.1 . . ?
C5 C4 H4D 109.1 . . ?
H4C C4 H4D 107.9 . . ?
C3 C4 C5 112.3(2) . . ?
C3 C4 H4C 109.1 . . ?
C3 C4 H4D 109.1 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C4 C3 C2 113.1(2) . . ?
H3A C3 H3B 107.8 . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
O5 C22 C23 107.0(2) . . ?
O5 C22 C21 113.3(2) . . ?
O5 C22 H22 108.7 . . ?
C23 C22 C21 110.4(2) . . ?
C23 C22 H22 108.7 . . ?
C21 C22 H22 108.7 . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.7(3) . . ?
C25 C24 H24 119.7 . . ?
C12 C17 C18 108.5(3) . . ?
C12 C17 C16 121.5(3) . . ?
C16 C17 C18 130.0(4) . . ?
C18 C10 C11 110.4(2) . . ?
C9 C10 C18 120.0(3) . . ?
C9 C10 C11 129.5(3) . . ?
C18 C19 H19 120.5 . . ?
C18 C19 C20 118.9(3) . . ?
C20 C19 H19 120.5 . . ?
C10 C11 H11A 111.2 . . ?
C10 C11 H11B 111.2 . . ?
C10 C11 C12 102.6(3) . . ?
H11A C11 H11B 109.2 . . ?
C12 C11 H11A 111.2 . . ?
C12 C11 H11B 111.2 . . ?
C17 C12 C11 110.3(3) . . ?
C13 C12 C17 120.8(3) . . ?
C13 C12 C11 128.9(4) . . ?
C8 C20 H20 119.7 . . ?
C19 C20 C8 120.6(3) . . ?
C19 C20 H20 119.7 . . ?
N3 C2 C3 110.1(2) . . ?
N3 C2 H2C 109.6 . . ?
N3 C2 H2D 109.6 . . ?
C3 C2 H2C 109.6 . . ?
C3 C2 H2D 109.6 . . ?
H2C C2 H2D 108.1 . . ?
C23 C28 H28 119.6 . . ?
C27 C28 C23 120.7(4) . . ?
C27 C28 H28 119.6 . . ?
C27 C26 H26 120.2 . . ?
C27 C26 C25 119.7(4) . . ?
C25 C26 H26 120.2 . . ?
C28 C27 H27 119.7 . . ?
C26 C27 C28 120.5(4) . . ?
C26 C27 H27 119.7 . . ?
C12 C13 H13 120.9 . . ?
C14 C13 C12 118.3(4) . . ?
C14 C13 H13 120.9 . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C14 C15 C16 122.2(4) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.5(4) . . ?
C26 C25 H25 119.8 . . ?
C17 C16 H16 121.7 . . ?
C15 C16 C17 116.6(5) . . ?
C15 C16 H16 121.7 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.6(4) . . ?
C15 C14 H14 119.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5A O2 0.82 1.92 2.723(3) 168.0 .
N4 H4B O1 0.90 1.83 2.732(3) 178.6 1_565
N1 H1A O4 0.86 2.16 2.871(3) 140.3 1_665
N1 H1B O4 0.86 1.99 2.847(3) 170.6 2_665

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.278 0.000 0.657 7.2 0.0 ?
2 0.500 -0.535 0.000 70.5 15.9 ?
3 0.722 0.500 0.343 7.2 0.0 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.807
