# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_AibFurea
_database_code_depnum_ccdc_archive 'CCDC 2354491'
loop_
_audit_author_name
_audit_author_address
'Souvik Dutta'
;IIT Delhi
India
;
_audit_update_record             
;
2024-05-10 deposited with the CCDC.	2024-09-18 downloaded from the CCDC.
;
_audit_creation_date             2024-03-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        MUAFO
_chemical_name_common            MUAFO
_chemical_formula_moiety         'C21 H25 N3 O4'
_chemical_formula_sum            'C21 H25 N3 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         383.450
_chemical_absolute_configuration S
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.3552(6)
_cell_length_b                   11.2241(13)
_cell_length_c                   33.850(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2034.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5463
_cell_measurement_temperature    304.(2)
_cell_measurement_theta_max      22.0180
_cell_measurement_theta_min      2.4067
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unk
_exptl_crystal_F_000             902
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            18534
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.333
_diffrn_reflns_theta_min         2.177
_diffrn_ambient_temperature      304.00
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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                   ?
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3123
_reflns_number_total             5035
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT, VERSION 2018/2'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 960 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5035
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.017
_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)+(0.0430P)²+0.3444P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1260
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H2 of N2, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, H1 of N1, H3 of N3
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3A), C4(H4), C5(H5), C6(H6), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_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 0.4348(4) 0.2799(2) 0.63994(6) 0.0467(6) Uani 1 1 d . . . . .
O2 O 0.4075(5) 0.8794(2) 0.65846(8) 0.0595(7) Uani 1 1 d . . . . .
O3 O 0.7375(4) 0.4864(2) 0.69714(7) 0.0545(6) Uani 1 1 d . . . . .
O4 O 0.0911(4) 0.7615(2) 0.67615(8) 0.0597(7) Uani 1 1 d . . . . .
N1 N 0.0159(5) 0.2641(3) 0.62828(8) 0.0468(7) Uani 1 1 d . . . . .
H1 H -0.137(8) 0.266(4) 0.6388(11) 0.070 Uiso 1 1 d . U . . .
N2 N 0.1605(5) 0.3391(2) 0.68708(7) 0.0401(6) Uani 1 1 d . . . . .
H2 H 0.006658 0.343463 0.694219 0.048 Uiso 1 1 calc R U . . .
N3 N 0.3775(5) 0.5662(2) 0.67670(8) 0.0401(7) Uani 1 1 d . . . . .
H3 H 0.220(7) 0.562(3) 0.6770(11) 0.060 Uiso 1 1 d . U . . .
C1 C 0.0225(6) 0.2022(3) 0.59170(10) 0.0438(8) Uani 1 1 d . . . . .
C2 C -0.1720(7) 0.1261(3) 0.58338(12) 0.0598(10) Uani 1 1 d . . . . .
H2A H -0.300140 0.115772 0.601604 0.072 Uiso 1 1 calc R U . . .
C3 C -0.1770(8) 0.0646(4) 0.54771(13) 0.0698(12) Uani 1 1 d . . . . .
H3A H -0.308984 0.013329 0.542236 0.084 Uiso 1 1 calc R U . . .
C4 C 0.0098(8) 0.0786(4) 0.52066(13) 0.0663(11) Uani 1 1 d . . . . .
H4 H 0.006716 0.036715 0.496969 0.080 Uiso 1 1 calc R U . . .
C5 C 0.2006(8) 0.1548(3) 0.52885(11) 0.0601(10) Uani 1 1 d . . . . .
H5 H 0.326304 0.165641 0.510239 0.072 Uiso 1 1 calc R U . . .
C6 C 0.2122(7) 0.2170(3) 0.56447(10) 0.0523(9) Uani 1 1 d . . . . .
H6 H 0.345439 0.267658 0.569808 0.063 Uiso 1 1 calc R U . . .
C7 C 0.2187(6) 0.2934(3) 0.65091(10) 0.0390(7) Uani 1 1 d . . . . .
C8 C 0.3563(6) 0.3809(3) 0.71396(9) 0.0391(7) Uani 1 1 d . . . . .
C9 C 0.5075(6) 0.4806(3) 0.69458(9) 0.0377(7) Uani 1 1 d . . . . .
C10 C 0.4925(6) 0.6752(3) 0.66205(9) 0.0400(7) Uani 1 1 d . . . . .
H10 H 0.636842 0.693272 0.678813 0.048 Uiso 1 1 calc R U . . .
C11 C 0.3046(6) 0.7742(3) 0.66690(9) 0.0414(7) Uani 1 1 d . . . . .
C12 C 0.2406(10) 0.9811(3) 0.65938(16) 0.0886(15) Uani 1 1 d . . . . .
H12A H 0.332860 1.052309 0.653531 0.133 Uiso 1 1 calc R U . . .
H12B H 0.167194 0.987811 0.685163 0.133 Uiso 1 1 calc R U . . .
H12C H 0.111198 0.970618 0.640064 0.133 Uiso 1 1 calc R U . . .
C13 C 0.5241(7) 0.2780(3) 0.72717(10) 0.0523(9) Uani 1 1 d . . . . .
H13A H 0.648448 0.307353 0.745128 0.078 Uiso 1 1 calc R U . . .
H13B H 0.604385 0.243570 0.704521 0.078 Uiso 1 1 calc R U . . .
H13C H 0.424834 0.218478 0.740140 0.078 Uiso 1 1 calc R U . . .
C14 C 0.2282(7) 0.4340(3) 0.75042(10) 0.0513(9) Uani 1 1 d . . . . .
H14A H 0.352339 0.465223 0.768071 0.077 Uiso 1 1 calc R U . . .
H14B H 0.133981 0.373164 0.763635 0.077 Uiso 1 1 calc R U . . .
H14C H 0.118082 0.497016 0.742376 0.077 Uiso 1 1 calc R U . . .
C15 C 0.5837(6) 0.6657(3) 0.61928(10) 0.0521(9) Uani 1 1 d . . . . .
H15A H 0.679372 0.736554 0.612923 0.063 Uiso 1 1 calc R U . . .
H15B H 0.694771 0.597802 0.617111 0.063 Uiso 1 1 calc R U . . .
C16 C 0.3774(6) 0.6524(3) 0.58951(10) 0.0472(9) Uani 1 1 d . . . . .
C17 C 0.2733(7) 0.5429(3) 0.58192(10) 0.0543(9) Uani 1 1 d . . . . .
H17 H 0.337272 0.475917 0.594519 0.065 Uiso 1 1 calc R U . . .
C18 C 0.0750(8) 0.5300(4) 0.55594(11) 0.0631(11) Uani 1 1 d . . . . .
H18 H 0.005583 0.455111 0.551708 0.076 Uiso 1 1 calc R U . . .
C19 C -0.0182(8) 0.6265(4) 0.53661(11) 0.0634(11) Uani 1 1 d . . . . .
H19 H -0.149895 0.617728 0.518927 0.076 Uiso 1 1 calc R U . . .
C20 C 0.0834(8) 0.7366(4) 0.54338(11) 0.0668(11) Uani 1 1 d . . . . .
H20 H 0.020393 0.802828 0.530212 0.080 Uiso 1 1 calc R U . . .
C21 C 0.2792(8) 0.7500(3) 0.56972(11) 0.0612(10) Uani 1 1 d . . . . .
H21 H 0.345702 0.825284 0.574215 0.073 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.225(4) . ?
O2 C11 1.334(4) . ?
O2 C12 1.450(5) . ?
O3 C9 1.236(4) . ?
O4 C11 1.194(4) . ?
N1 H1 0.89(4) . ?
N1 C1 1.421(4) . ?
N1 C7 1.369(4) . ?
N2 H2 0.8600 . ?
N2 C7 1.364(4) . ?
N2 C8 1.465(4) . ?
N3 H3 0.85(4) . ?
N3 C9 1.332(4) . ?
N3 C10 1.457(4) . ?
C1 C2 1.376(5) . ?
C1 C6 1.382(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.391(5) . ?
C3 H3A 0.9300 . ?
C3 C4 1.365(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.361(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.395(5) . ?
C6 H6 0.9300 . ?
C8 C9 1.529(4) . ?
C8 C13 1.530(4) . ?
C8 C14 1.533(4) . ?
C10 H10 0.9800 . ?
C10 C11 1.509(4) . ?
C10 C15 1.531(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.503(5) . ?
C16 C17 1.373(5) . ?
C16 C21 1.388(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.360(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.370(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(5) . ?
C21 H21 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
C11 O2 C12 115.9(3) . . ?
C1 N1 H1 113(3) . . ?
C7 N1 H1 120(2) . . ?
C7 N1 C1 125.8(3) . . ?
C7 N2 H2 119.5 . . ?
C7 N2 C8 121.0(3) . . ?
C8 N2 H2 119.5 . . ?
C9 N3 H3 119(3) . . ?
C9 N3 C10 122.6(3) . . ?
C10 N3 H3 118(3) . . ?
C2 C1 N1 117.6(3) . . ?
C2 C1 C6 119.7(3) . . ?
C6 C1 N1 122.7(3) . . ?
C1 C2 H2A 120.0 . . ?
C1 C2 C3 120.0(4) . . ?
C3 C2 H2A 120.0 . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3A 119.6 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.1(4) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.6(4) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 118.9(4) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
O1 C7 N1 123.4(3) . . ?
O1 C7 N2 122.3(3) . . ?
N2 C7 N1 114.3(3) . . ?
N2 C8 C9 110.3(2) . . ?
N2 C8 C13 111.1(3) . . ?
N2 C8 C14 107.7(3) . . ?
C9 C8 C14 107.3(3) . . ?
C13 C8 C9 111.5(3) . . ?
C13 C8 C14 108.7(3) . . ?
O3 C9 N3 121.0(3) . . ?
O3 C9 C8 122.4(3) . . ?
N3 C9 C8 116.5(3) . . ?
N3 C10 H10 108.1 . . ?
N3 C10 C11 107.4(2) . . ?
N3 C10 C15 113.5(3) . . ?
C11 C10 H10 108.1 . . ?
C11 C10 C15 111.5(3) . . ?
C15 C10 H10 108.1 . . ?
O2 C11 C10 110.7(3) . . ?
O4 C11 O2 123.9(3) . . ?
O4 C11 C10 125.4(3) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 108.8 . . ?
C10 C15 H15B 108.8 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C10 114.0(3) . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 C21 117.5(3) . . ?
C21 C16 C15 121.6(3) . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.6(3) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(4) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.5(4) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.4(4) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.8(4) . . ?
C20 C21 H21 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 179.0(3) . . . . ?
N1 C1 C6 C5 -178.4(3) . . . . ?
N2 C8 C9 O3 -137.9(3) . . . . ?
N2 C8 C9 N3 46.3(4) . . . . ?
N3 C10 C11 O2 172.6(3) . . . . ?
N3 C10 C11 O4 -8.9(4) . . . . ?
N3 C10 C15 C16 66.9(4) . . . . ?
C1 N1 C7 O1 8.0(5) . . . . ?
C1 N1 C7 N2 -171.9(3) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C2 C1 C6 C5 0.5(5) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C3 C4 C5 C6 1.2(6) . . . . ?
C4 C5 C6 C1 -1.2(6) . . . . ?
C6 C1 C2 C3 0.0(5) . . . . ?
C7 N1 C1 C2 145.6(3) . . . . ?
C7 N1 C1 C6 -35.5(5) . . . . ?
C7 N2 C8 C9 59.4(4) . . . . ?
C7 N2 C8 C13 -64.8(4) . . . . ?
C7 N2 C8 C14 176.2(3) . . . . ?
C8 N2 C7 O1 3.5(5) . . . . ?
C8 N2 C7 N1 -176.6(3) . . . . ?
C9 N3 C10 C11 -146.4(3) . . . . ?
C9 N3 C10 C15 89.8(4) . . . . ?
C10 N3 C9 O3 -5.0(5) . . . . ?
C10 N3 C9 C8 170.8(3) . . . . ?
C10 C15 C16 C17 -82.7(4) . . . . ?
C10 C15 C16 C21 95.0(4) . . . . ?
C11 C10 C15 C16 -54.6(4) . . . . ?
C12 O2 C11 O4 -2.6(5) . . . . ?
C12 O2 C11 C10 175.9(3) . . . . ?
C13 C8 C9 O3 -14.0(4) . . . . ?
C13 C8 C9 N3 170.3(3) . . . . ?
C14 C8 C9 O3 105.0(4) . . . . ?
C14 C8 C9 N3 -70.7(3) . . . . ?
C15 C10 C11 O2 -62.5(3) . . . . ?
C15 C10 C11 O4 116.0(4) . . . . ?
C15 C16 C17 C18 176.9(3) . . . . ?
C15 C16 C21 C20 -177.8(3) . . . . ?
C16 C17 C18 C19 1.3(6) . . . . ?
C17 C16 C21 C20 0.0(5) . . . . ?
C17 C18 C19 C20 -0.8(6) . . . . ?
C18 C19 C20 C21 -0.1(6) . . . . ?
C19 C20 C21 C16 0.5(6) . . . . ?
C21 C16 C17 C18 -0.9(5) . . . . ?

_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_dFAibUrea
_database_code_depnum_ccdc_archive 'CCDC 2354492'
loop_
_audit_author_name
_audit_author_address
'Souvik Dutta'
;IIT Delhi
India
;
_audit_update_record             
;
2024-05-10 deposited with the CCDC.	2024-09-18 downloaded from the CCDC.
;
_audit_creation_date             2024-03-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            dMUAFO
_chemical_name_systematic        dMUAFO
_chemical_formula_moiety         'C21 H25 N3 O4'
_chemical_formula_sum            'C21 H25 N3 O4'
_chemical_formula_weight         383.1845
_chemical_absolute_configuration R
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.3547(2)
_cell_length_b                   11.2231(4)
_cell_length_c                   33.8405(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2033.69(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4616
_cell_measurement_temperature    302.(2)
_cell_measurement_theta_max      21.1445
_cell_measurement_theta_min      2.1775
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unk
_exptl_crystal_F_000             816
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            19171
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.255
_diffrn_reflns_theta_min         2.178
_diffrn_ambient_temperature      302.00
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                   ?
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2928
_reflns_number_total             5027
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT, VERSION 2018/2'
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 879 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         5027
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.000
_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)+(0.0501P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1207
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), C2(H2A), C3(H3A), C4(H4), C5(H5), C6(H6), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_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 0.4352(4) 0.72008(19) 0.63989(6) 0.0497(6) Uani 1 1 d . . . . .
O2 O 0.4073(4) 0.12032(19) 0.65845(7) 0.0617(7) Uani 1 1 d . . . . .
O3 O 0.7384(4) 0.5137(2) 0.69718(7) 0.0567(6) Uani 1 1 d . . . . .
O4 O 0.0910(4) 0.23832(19) 0.67606(7) 0.0619(7) Uani 1 1 d . . . . .
N1 N 0.0159(4) 0.7360(2) 0.62840(7) 0.0479(7) Uani 1 1 d . . . . .
H1 H -0.128469 0.715393 0.637204 0.058 Uiso 1 1 calc R U . . .
N2 N 0.1612(4) 0.6608(2) 0.68709(7) 0.0431(6) Uani 1 1 d . . . . .
H2 H 0.007305 0.656495 0.694202 0.052 Uiso 1 1 calc R U . . .
N3 N 0.3766(4) 0.4335(2) 0.67675(7) 0.0413(6) Uani 1 1 d . . . . .
H3 H 0.218443 0.443035 0.673707 0.050 Uiso 1 1 calc R U . . .
C1 C 0.0230(5) 0.7979(3) 0.59171(9) 0.0438(7) Uani 1 1 d . . . . .
C2 C 0.2107(6) 0.7832(3) 0.56443(10) 0.0537(8) Uani 1 1 d . . . . .
H2A H 0.343335 0.732122 0.569730 0.064 Uiso 1 1 calc R U . . .
C3 C 0.2012(7) 0.8451(3) 0.52884(10) 0.0616(10) Uani 1 1 d . . . . .
H3A H 0.327316 0.834348 0.510284 0.074 Uiso 1 1 calc R U . . .
C4 C 0.0093(7) 0.9213(4) 0.52080(12) 0.0691(11) Uani 1 1 d . . . . .
H4 H 0.005972 0.963659 0.497180 0.083 Uiso 1 1 calc R U . . .
C5 C -0.1778(7) 0.9347(4) 0.54786(13) 0.0731(12) Uani 1 1 d . . . . .
H5 H -0.310532 0.985509 0.542398 0.088 Uiso 1 1 calc R U . . .
C6 C -0.1719(6) 0.8734(3) 0.58331(11) 0.0623(10) Uani 1 1 d . . . . .
H6 H -0.300303 0.883291 0.601522 0.075 Uiso 1 1 calc R U . . .
C7 C 0.2192(5) 0.7065(3) 0.65082(9) 0.0401(7) Uani 1 1 d . . . . .
C8 C 0.3555(5) 0.6190(3) 0.71401(9) 0.0418(7) Uani 1 1 d . . . . .
C9 C 0.5088(5) 0.5192(3) 0.69462(8) 0.0401(7) Uani 1 1 d . . . . .
C10 C 0.4929(5) 0.3244(2) 0.66229(9) 0.0416(7) Uani 1 1 d . . . . .
H10 H 0.636806 0.306246 0.679137 0.050 Uiso 1 1 calc R U . . .
C11 C 0.3043(6) 0.2256(3) 0.66682(9) 0.0431(7) Uani 1 1 d . . . . .
C12 C 0.2395(8) 0.0189(3) 0.65940(15) 0.0892(14) Uani 1 1 d . . . . .
H12A H 0.328862 -0.051720 0.651880 0.134 Uiso 1 1 calc R U . . .
H12B H 0.104172 0.031971 0.641315 0.134 Uiso 1 1 calc R U . . .
H12C H 0.174512 0.009273 0.685649 0.134 Uiso 1 1 calc R U . . .
C13 C 0.5245(6) 0.7224(3) 0.72717(10) 0.0554(9) Uani 1 1 d . . . . .
H13A H 0.648857 0.693140 0.745157 0.083 Uiso 1 1 calc R U . . .
H13B H 0.425463 0.782125 0.740100 0.083 Uiso 1 1 calc R U . . .
H13C H 0.604831 0.756591 0.704480 0.083 Uiso 1 1 calc R U . . .
C14 C 0.2287(6) 0.5657(3) 0.75051(10) 0.0543(9) Uani 1 1 d . . . . .
H14A H 0.353014 0.531811 0.767592 0.081 Uiso 1 1 calc R U . . .
H14B H 0.113795 0.504726 0.742442 0.081 Uiso 1 1 calc R U . . .
H14C H 0.139944 0.627116 0.764382 0.081 Uiso 1 1 calc R U . . .
C15 C 0.5842(6) 0.3343(3) 0.61936(9) 0.0539(9) Uani 1 1 d . . . . .
H15A H 0.694560 0.402493 0.617208 0.065 Uiso 1 1 calc R U . . .
H15B H 0.680724 0.263701 0.612959 0.065 Uiso 1 1 calc R U . . .
C16 C 0.3762(6) 0.3473(3) 0.58941(9) 0.0480(8) Uani 1 1 d . . . . .
C17 C 0.2793(7) 0.2501(3) 0.56958(10) 0.0617(9) Uani 1 1 d . . . . .
H17 H 0.346869 0.174907 0.573941 0.074 Uiso 1 1 calc R U . . .
C18 C 0.0829(7) 0.2632(4) 0.54330(10) 0.0673(10) Uani 1 1 d . . . . .
H18 H 0.020061 0.196851 0.530161 0.081 Uiso 1 1 calc R U . . .
C19 C -0.0193(7) 0.3733(3) 0.53653(10) 0.0646(10) Uani 1 1 d . . . . .
H19 H -0.151834 0.381958 0.519000 0.077 Uiso 1 1 calc R U . . .
C20 C 0.0756(7) 0.4701(3) 0.55584(10) 0.0661(10) Uani 1 1 d . . . . .
H20 H 0.007242 0.545067 0.551377 0.079 Uiso 1 1 calc R U . . .
C21 C 0.2726(7) 0.4575(3) 0.58198(10) 0.0569(9) Uani 1 1 d . . . . .
H21 H 0.336041 0.524427 0.594720 0.068 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.224(3) . ?
O2 C11 1.334(3) . ?
O2 C12 1.450(4) . ?
O3 C9 1.234(3) . ?
O4 C11 1.193(3) . ?
N1 H1 0.8600 . ?
N1 C1 1.423(4) . ?
N1 C7 1.368(4) . ?
N2 H2 0.8600 . ?
N2 C7 1.366(4) . ?
N2 C8 1.460(4) . ?
N3 H3 0.8600 . ?
N3 C9 1.339(4) . ?
N3 C10 1.458(4) . ?
C1 C2 1.375(4) . ?
C1 C6 1.374(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.391(5) . ?
C3 H3A 0.9300 . ?
C3 C4 1.365(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.365(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(5) . ?
C6 H6 0.9300 . ?
C8 C9 1.536(4) . ?
C8 C13 1.538(4) . ?
C8 C14 1.531(4) . ?
C10 H10 0.9800 . ?
C10 C11 1.508(4) . ?
C10 C15 1.537(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.513(4) . ?
C16 C17 1.382(4) . ?
C16 C21 1.379(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.371(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.366(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(5) . ?
C21 H21 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
C11 O2 C12 115.7(3) . . ?
C1 N1 H1 117.3 . . ?
C7 N1 H1 117.3 . . ?
C7 N1 C1 125.5(2) . . ?
C7 N2 H2 119.4 . . ?
C7 N2 C8 121.3(2) . . ?
C8 N2 H2 119.4 . . ?
C9 N3 H3 119.0 . . ?
C9 N3 C10 122.0(2) . . ?
C10 N3 H3 119.0 . . ?
C2 C1 N1 123.1(3) . . ?
C6 C1 N1 117.5(3) . . ?
C6 C1 C2 119.4(3) . . ?
C1 C2 H2A 120.2 . . ?
C1 C2 C3 119.6(3) . . ?
C3 C2 H2A 120.2 . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3A 119.6 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 120.2(4) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
O1 C7 N1 123.7(3) . . ?
O1 C7 N2 122.2(3) . . ?
N2 C7 N1 114.1(2) . . ?
N2 C8 C9 110.4(2) . . ?
N2 C8 C13 111.0(2) . . ?
N2 C8 C14 108.2(2) . . ?
C9 C8 C13 111.1(2) . . ?
C14 C8 C9 107.2(2) . . ?
C14 C8 C13 108.8(2) . . ?
O3 C9 N3 121.5(3) . . ?
O3 C9 C8 122.6(3) . . ?
N3 C9 C8 115.8(2) . . ?
N3 C10 H10 108.3 . . ?
N3 C10 C11 107.3(2) . . ?
N3 C10 C15 113.1(2) . . ?
C11 C10 H10 108.3 . . ?
C11 C10 C15 111.3(2) . . ?
C15 C10 H10 108.3 . . ?
O2 C11 C10 110.7(2) . . ?
O4 C11 O2 123.9(3) . . ?
O4 C11 C10 125.5(3) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 108.8 . . ?
C10 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 C10 113.9(2) . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C17 C16 C15 121.7(3) . . ?
C21 C16 C15 120.3(3) . . ?
C21 C16 C17 117.9(3) . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.9(3) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.4 . . ?
C20 C19 C18 119.2(4) . . ?
C20 C19 H19 120.4 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.6(3) . . ?
C21 C20 H20 119.7 . . ?
C16 C21 C20 121.0(3) . . ?
C16 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 178.5(3) . . . . ?
N1 C1 C6 C5 -179.0(3) . . . . ?
N2 C8 C9 O3 137.5(3) . . . . ?
N2 C8 C9 N3 -46.7(3) . . . . ?
N3 C10 C11 O2 -172.8(2) . . . . ?
N3 C10 C11 O4 8.1(4) . . . . ?
N3 C10 C15 C16 -66.9(4) . . . . ?
C1 N1 C7 O1 -7.4(5) . . . . ?
C1 N1 C7 N2 172.1(3) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
C2 C1 C6 C5 -0.6(5) . . . . ?
C2 C3 C4 C5 -1.4(6) . . . . ?
C3 C4 C5 C6 1.0(6) . . . . ?
C4 C5 C6 C1 -0.1(6) . . . . ?
C6 C1 C2 C3 0.3(5) . . . . ?
C7 N1 C1 C2 35.4(5) . . . . ?
C7 N1 C1 C6 -146.3(3) . . . . ?
C7 N2 C8 C9 -59.0(3) . . . . ?
C7 N2 C8 C13 64.5(3) . . . . ?
C7 N2 C8 C14 -176.1(3) . . . . ?
C8 N2 C7 O1 -3.6(4) . . . . ?
C8 N2 C7 N1 176.9(3) . . . . ?
C9 N3 C10 C11 147.0(3) . . . . ?
C9 N3 C10 C15 -89.9(3) . . . . ?
C10 N3 C9 O3 5.3(4) . . . . ?
C10 N3 C9 C8 -170.6(2) . . . . ?
C10 C15 C16 C17 -95.1(4) . . . . ?
C10 C15 C16 C21 83.0(4) . . . . ?
C11 C10 C15 C16 54.0(4) . . . . ?
C12 O2 C11 O4 2.7(5) . . . . ?
C12 O2 C11 C10 -176.3(3) . . . . ?
C13 C8 C9 O3 14.0(4) . . . . ?
C13 C8 C9 N3 -170.2(3) . . . . ?
C14 C8 C9 O3 -104.8(3) . . . . ?
C14 C8 C9 N3 71.0(3) . . . . ?
C15 C10 C11 O2 63.0(3) . . . . ?
C15 C10 C11 O4 -116.1(3) . . . . ?
C15 C16 C17 C18 177.7(3) . . . . ?
C15 C16 C21 C20 -177.4(3) . . . . ?
C16 C17 C18 C19 -0.1(5) . . . . ?
C17 C16 C21 C20 0.8(5) . . . . ?
C17 C18 C19 C20 0.4(6) . . . . ?
C18 C19 C20 C21 -0.1(6) . . . . ?
C19 C20 C21 C16 -0.5(5) . . . . ?
C21 C16 C17 C18 -0.5(5) . . . . ?

_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_FFUrea
_database_code_depnum_ccdc_archive 'CCDC 2354493'
loop_
_audit_author_name
_audit_author_address
'Souvik Dutta'
;IIT Delhi
India
;
_audit_update_record             
;
2024-05-10 deposited with the CCDC.	2024-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1

_chemical_name_systematic        MUFFO
_chemical_name_common            MUFFO
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H27 N3 O4'
_chemical_formula_sum            'C26 H27 N3 O4'
_chemical_formula_weight         445.51

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'

_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'

_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'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'

_cell_length_a                   12.7958(3)
_cell_length_b                   12.7958(3)
_cell_length_c                   26.2968(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3728.8(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9688
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      23.16

_exptl_crystal_description       unk
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_F_000             1416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            166845
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.994
_diffrn_reflns_theta_max         26.384
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5074
_reflns_number_gt                4665
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.957
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0401P)²+0.5535P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2113 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_chemical_absolute_configuration S
_refine_ls_number_reflns         5074
_refine_ls_number_parameters     299
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0830
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.056
_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
O1 O 0.47309(16) 1.28620(18) 0.54061(7) 0.0490(5) Uani 1 1 d . . . . .
O2 O 0.38026(18) 1.38936(17) 0.52022(9) 0.0626(6) Uani 1 1 d . . . . .
O3 O 0.18286(15) 1.11509(16) 0.56586(6) 0.0420(4) Uani 1 1 d . . . . .
O4 O -0.04241(15) 0.86801(14) 0.49654(5) 0.0351(3) Uani 1 1 d . . . . .
N1 N -0.07172(16) 0.97951(15) 0.55554(6) 0.0290(4) Uani 1 1 d . . . . .
H1 H -0.111299 0.979484 0.582906 0.035 Uiso 1 1 calc R U . . .
N2 N 0.19131(16) 1.16269(17) 0.48330(6) 0.0321(4) Uani 1 1 d . . . . .
H2 H 0.152560 1.166733 0.456404 0.038 Uiso 1 1 calc R U . . .
N3 N -0.12503(17) 0.78492(15) 0.57354(6) 0.0327(4) Uani 1 1 d . . . . .
H3 H -0.157681 0.796373 0.600887 0.039 Uiso 1 1 calc R U . . .
C1 C 0.4872(2) 1.2750(2) 0.41318(8) 0.0380(5) Uani 1 1 d . . . . .
C2 C 0.5114(3) 1.1874(3) 0.39582(10) 0.0550(7) Uani 1 1 d . . . . .
H2A H 0.447768 1.106376 0.392217 0.066 Uiso 1 1 calc R U . . .
C3 C 0.6282(4) 1.2179(4) 0.38374(13) 0.0745(10) Uani 1 1 d . . . . .
H3A H 0.644583 1.157340 0.371951 0.089 Uiso 1 1 calc R U . . .
C4 C 0.7208(3) 1.3343(5) 0.38853(13) 0.0782(12) Uani 1 1 d . . . . .
H4 H 0.800905 1.354347 0.380066 0.094 Uiso 1 1 calc R U . . .
C5 C 0.6975(3) 1.4224(4) 0.40565(12) 0.0687(9) Uani 1 1 d . . . . .
H5 H 0.761377 1.503407 0.408759 0.082 Uiso 1 1 calc R U . . .
C6 C 0.5808(2) 1.3924(3) 0.41833(9) 0.0488(6) Uani 1 1 d . . . . .
H6 H 0.564957 1.452951 0.430638 0.059 Uiso 1 1 calc R U . . .
C7 C 0.3587(2) 1.2407(2) 0.42441(9) 0.0406(5) Uani 1 1 d . . . . .
H7A H 0.304901 1.174499 0.401234 0.049 Uiso 1 1 calc R U . . .
H7B H 0.348255 1.310808 0.416924 0.049 Uiso 1 1 calc R U . . .
C8 C 0.31880(19) 1.2003(2) 0.47938(8) 0.0305(4) Uani 1 1 d . . . . .
H8 H 0.330496 1.130570 0.487637 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3917(2) 1.3027(2) 0.51590(9) 0.0371(5) Uani 1 1 d . . . . .
C10 C 0.5499(3) 1.3824(4) 0.57549(14) 0.0843(12) Uani 1 1 d . . . . .
H10A H 0.607068 1.362874 0.591678 0.127 Uiso 1 1 calc R U . . .
H10B H 0.500025 1.390776 0.601629 0.127 Uiso 1 1 calc R U . . .
H10C H 0.594535 1.458361 0.556690 0.127 Uiso 1 1 calc R U . . .
C11 C 0.13287(19) 1.12231(17) 0.52703(8) 0.0294(4) Uani 1 1 d . . . . .
C12 C 0.00066(18) 1.09024(18) 0.52726(8) 0.0286(4) Uani 1 1 d . . . . .
H12 H -0.029451 1.079021 0.491457 0.034 Uiso 1 1 calc R U . . .
C13 C -0.07767(19) 0.87594(18) 0.53928(7) 0.0276(4) Uani 1 1 d . . . . .
C14 C -0.1277(2) 0.67323(18) 0.57010(8) 0.0314(4) Uani 1 1 d . . . . .
C15 C -0.1271(2) 0.6187(2) 0.61558(8) 0.0377(5) Uani 1 1 d . . . . .
H15 H -0.124970 0.656559 0.646936 0.045 Uiso 1 1 calc R U . . .
C16 C -0.1296(2) 0.5094(2) 0.61551(9) 0.0451(6) Uani 1 1 d . . . . .
H16 H -0.129424 0.472332 0.646767 0.054 Uiso 1 1 calc R U . . .
C17 C -0.1325(3) 0.4543(2) 0.57012(10) 0.0465(6) Uani 1 1 d . . . . .
H17 H -0.132816 0.379890 0.570022 0.056 Uiso 1 1 calc R U . . .
C18 C -0.1348(3) 0.5074(2) 0.52489(10) 0.0476(6) Uani 1 1 d . . . . .
H18 H -0.137864 0.468524 0.493684 0.057 Uiso 1 1 calc R U . . .
C19 C -0.1328(2) 0.6172(2) 0.52428(9) 0.0405(5) Uani 1 1 d . . . . .
H19 H -0.134944 0.653154 0.492980 0.049 Uiso 1 1 calc R U . . .
C20 C -0.0089(2) 1.19370(19) 0.55186(8) 0.0338(5) Uani 1 1 d . . . . .
H20A H 0.026610 1.208396 0.586382 0.041 Uiso 1 1 calc R U . . .
H20B H 0.039106 1.268028 0.531645 0.041 Uiso 1 1 calc R U . . .
C21 C -0.1366(2) 1.16901(18) 0.55573(9) 0.0334(5) Uani 1 1 d . . . . .
C22 C -0.1957(2) 1.1423(2) 0.60210(10) 0.0451(6) Uani 1 1 d . . . . .
H22 H -0.156078 1.137471 0.631799 0.054 Uiso 1 1 calc R U . . .
C23 C -0.3134(3) 1.1224(3) 0.60554(14) 0.0617(8) Uani 1 1 d . . . . .
H23 H -0.353598 1.103732 0.637437 0.074 Uiso 1 1 calc R U . . .
C24 C -0.3705(3) 1.1298(3) 0.56276(16) 0.0674(9) Uani 1 1 d . . . . .
H24 H -0.450130 1.117165 0.565192 0.081 Uiso 1 1 calc R U . . .
C25 C -0.3138(3) 1.1553(3) 0.51664(14) 0.0606(8) Uani 1 1 d . . . . .
H25 H -0.354452 1.159442 0.487137 0.073 Uiso 1 1 calc R U . . .
C26 C -0.1970(2) 1.1753(2) 0.51271(10) 0.0438(6) Uani 1 1 d . . . . .
H26 H -0.157983 1.193259 0.480545 0.053 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.331(3) . ?
O1 C10 1.454(4) . ?
O2 C9 1.194(3) . ?
O3 C11 1.233(3) . ?
O4 C13 1.234(2) . ?
N1 C13 1.358(3) . ?
N1 C12 1.451(3) . ?
N2 C11 1.328(3) . ?
N2 C8 1.455(3) . ?
N3 C13 1.353(3) . ?
N3 C14 1.415(3) . ?
C1 C2 1.381(4) . ?
C1 C6 1.382(4) . ?
C1 C7 1.505(3) . ?
C2 C3 1.380(4) . ?
C3 C4 1.369(6) . ?
C4 C5 1.377(6) . ?
C5 C6 1.384(4) . ?
C7 C8 1.534(3) . ?
C8 C9 1.512(3) . ?
C11 C12 1.528(3) . ?
C12 C20 1.532(3) . ?
C14 C15 1.387(3) . ?
C14 C19 1.387(3) . ?
C15 C16 1.382(3) . ?
C16 C17 1.378(4) . ?
C17 C18 1.377(4) . ?
C18 C19 1.393(3) . ?
C20 C21 1.505(3) . ?
C21 C22 1.385(3) . ?
C21 C26 1.395(3) . ?
C22 C23 1.399(4) . ?
C23 C24 1.371(5) . ?
C24 C25 1.367(5) . ?
C25 C26 1.389(4) . ?

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
C9 O1 C10 115.2(2) . . ?
C13 N1 C12 119.25(16) . . ?
C11 N2 C8 120.68(18) . . ?
C13 N3 C14 126.95(17) . . ?
C2 C1 C6 119.4(2) . . ?
C2 C1 C7 118.9(2) . . ?
C6 C1 C7 121.6(2) . . ?
C3 C2 C1 119.8(3) . . ?
C4 C3 C2 120.8(3) . . ?
C3 C4 C5 119.8(3) . . ?
C4 C5 C6 119.8(3) . . ?
C1 C6 C5 120.4(3) . . ?
C1 C7 C8 114.47(18) . . ?
N2 C8 C9 110.23(17) . . ?
N2 C8 C7 107.90(17) . . ?
C9 C8 C7 110.44(19) . . ?
O2 C9 O1 124.8(2) . . ?
O2 C9 C8 123.7(2) . . ?
O1 C9 C8 111.43(19) . . ?
O3 C11 N2 122.3(2) . . ?
O3 C11 C12 121.53(18) . . ?
N2 C11 C12 116.12(18) . . ?
N1 C12 C11 110.15(16) . . ?
N1 C12 C20 109.85(17) . . ?
C11 C12 C20 108.97(17) . . ?
O4 C13 N3 124.10(18) . . ?
O4 C13 N1 121.50(18) . . ?
N3 C13 N1 114.39(17) . . ?
C15 C14 C19 120.0(2) . . ?
C15 C14 N3 116.73(19) . . ?
C19 C14 N3 123.27(19) . . ?
C16 C15 C14 120.3(2) . . ?
C17 C16 C15 120.0(2) . . ?
C18 C17 C16 119.8(2) . . ?
C17 C18 C19 120.9(2) . . ?
C14 C19 C18 118.9(2) . . ?
C21 C20 C12 113.22(17) . . ?
C22 C21 C26 118.6(2) . . ?
C22 C21 C20 120.9(2) . . ?
C26 C21 C20 120.5(2) . . ?
C21 C22 C23 120.5(3) . . ?
C24 C23 C22 119.8(3) . . ?
C25 C24 C23 120.4(3) . . ?
C24 C25 C26 120.3(3) . . ?
C25 C26 C21 120.4(3) . . ?

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.029



