# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_pro-c(o)-nh-nme-c(o)phCF3_a
_database_code_depnum_ccdc_archive 'CCDC 2239865'
loop_
_audit_author_name
_audit_author_address
'Jugal Kishore Rai Deka'
;Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR), Bangalore
India
;
_audit_update_record             
;
2023-02-04 deposited with the CCDC.	2023-04-20 downloaded from the CCDC.
;
_audit_creation_date             2023-02-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 F3 N3 O3, H2 O'
_chemical_formula_sum            'C16 H20 F3 N3 O4'
_chemical_formula_weight         375.35
_chemical_absolute_configuration ad
_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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
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                   16.380(3)
_cell_length_b                   6.0768(12)
_cell_length_c                   18.447(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.389(9)
_cell_angle_gamma                90
_cell_volume                     1833.0(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2345
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      23.38
_cell_measurement_theta_min      2.21
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.078
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10302
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.023
_diffrn_reflns_theta_min         2.212
_diffrn_ambient_temperature      300.01
_diffrn_detector_area_resol_mean ?
_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                   x-ray
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                1986
_reflns_number_total             3596
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 640 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(7)
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3596
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0596
_refine_ls_restrained_S_all      0.997
_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)+(0.1045P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1572
_refine_ls_wR_factor_ref         0.1950
_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, All O(H,H) groups
2.a Free rotating group:
 O4(H4c,H4d)
2.b Ternary CH refined with riding coordinates:
 C6(H6)
2.c Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C5(H5a,H5b), C4(H4a,H4b)
2.d Aromatic/amide H refined with riding coordinates:
 N2(H2), C11(H11), C12(H12), C15(H15), C14(H14)
2.e Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C1(H1a,H1b,H1c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.8097(3) 0.2577(7) 0.0674(2) 0.0750(12) Uani 1 1 d . . . . .
N2 N 0.6717(3) 0.5169(8) 0.1721(2) 0.0562(12) Uani 1 1 d . . . . .
H2 H 0.707764 0.619412 0.170308 0.067 Uiso 1 1 calc R U . . .
N1 N 0.8368(3) 0.4171(8) 0.1747(2) 0.0610(13) Uani 1 1 d . . . . .
N3 N 0.5896(3) 0.5572(9) 0.1548(2) 0.0602(12) Uani 1 1 d . . . . .
O2 O 0.6432(3) 0.1673(8) 0.2020(2) 0.0826(14) Uani 1 1 d . . . . .
O4 O 0.7440(4) 0.8241(8) 0.0785(2) 0.0922(16) Uani 1 1 d G . . . .
H4C H 0.728252 0.784932 0.035729 0.138 Uiso 1 1 d G U . . .
H4D H 0.756388 0.959183 0.074524 0.138 Uiso 1 1 d G U . . .
O3 O 0.4625(2) 0.5414(10) 0.1940(2) 0.0882(14) Uani 1 1 d . . . . .
C7 C 0.6929(4) 0.3072(11) 0.1921(3) 0.0598(15) Uani 1 1 d . . . . .
C9 C 0.5365(3) 0.5561(10) 0.2082(3) 0.0620(15) Uani 1 1 d . . . . .
C10 C 0.5698(3) 0.5796(10) 0.2847(3) 0.0575(14) Uani 1 1 d . . . . .
C6 C 0.7822(3) 0.2700(10) 0.2105(3) 0.0598(15) Uani 1 1 d . . . . .
H6 H 0.795783 0.117960 0.198160 0.072 Uiso 1 1 calc R U . . .
C2 C 0.8496(4) 0.3925(11) 0.1045(3) 0.0654(16) Uani 1 1 d . . . . .
C13 C 0.6189(4) 0.6298(14) 0.4302(3) 0.081(2) Uani 1 1 d . . . . .
C11 C 0.6132(4) 0.7627(11) 0.3082(3) 0.0727(18) Uani 1 1 d . . . . .
H11 H 0.626814 0.869200 0.274794 0.087 Uiso 1 1 calc R U . . .
C12 C 0.6366(4) 0.7899(13) 0.3800(4) 0.0820(19) Uani 1 1 d . . . . .
H12 H 0.664428 0.916588 0.395271 0.098 Uiso 1 1 calc R U . . .
C15 C 0.5517(4) 0.4234(13) 0.3340(3) 0.0783(18) Uani 1 1 d . . . . .
H15 H 0.522412 0.299160 0.318567 0.094 Uiso 1 1 calc R U . . .
C14 C 0.5765(5) 0.4463(15) 0.4075(4) 0.092(2) Uani 1 1 d . . . . .
H14 H 0.564212 0.337611 0.440577 0.110 Uiso 1 1 calc R U . . .
C3 C 0.8842(4) 0.5589(13) 0.2263(4) 0.086(2) Uani 1 1 d . . . . .
H3A H 0.882861 0.711165 0.210545 0.103 Uiso 1 1 calc R U . . .
H3B H 0.940610 0.510601 0.232579 0.103 Uiso 1 1 calc R U . . .
C5 C 0.8041(5) 0.3068(16) 0.2914(3) 0.091(2) Uani 1 1 d . . . . .
H5A H 0.755749 0.299585 0.319129 0.110 Uiso 1 1 calc R U . . .
H5B H 0.843164 0.197562 0.309953 0.110 Uiso 1 1 calc R U . . .
C8 C 0.5616(4) 0.5141(14) 0.0794(3) 0.083(2) Uani 1 1 d . . . . .
H8A H 0.503099 0.527067 0.074324 0.124 Uiso 1 1 calc R U . . .
H8B H 0.577375 0.368106 0.066164 0.124 Uiso 1 1 calc R U . . .
H8C H 0.585843 0.618941 0.048225 0.124 Uiso 1 1 calc R U . . .
C1 C 0.9134(4) 0.5322(15) 0.0737(4) 0.098(2) Uani 1 1 d . . . . .
H1A H 0.966203 0.490825 0.094689 0.147 Uiso 1 1 calc R U . . .
H1B H 0.903081 0.683875 0.084493 0.147 Uiso 1 1 calc R U . . .
H1C H 0.912106 0.512194 0.022043 0.147 Uiso 1 1 calc R U . . .
C4 C 0.8404(5) 0.529(2) 0.2949(4) 0.123(3) Uani 1 1 d . . . . .
H4A H 0.797997 0.639898 0.298216 0.148 Uiso 1 1 calc R U . . .
H4B H 0.878368 0.542806 0.337073 0.148 Uiso 1 1 calc R U . . .
F1 F 0.6296(5) 0.4905(16) 0.5484(3) 0.193(4) Uani 1 1 d . . . . .
F3 F 0.6030(6) 0.8146(19) 0.5360(4) 0.247(5) Uani 1 1 d . . . . .
F2 F 0.7183(4) 0.7018(14) 0.5213(3) 0.171(3) Uani 1 1 d . . . . .
C16 C 0.6426(6) 0.662(2) 0.5063(5) 0.117(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.231(7) . ?
N2 H2 0.8600 . ?
N2 N3 1.387(6) . ?
N2 C7 1.366(8) . ?
N1 C6 1.450(7) . ?
N1 C2 1.331(7) . ?
N1 C3 1.472(7) . ?
N3 C9 1.352(7) . ?
N3 C8 1.462(7) . ?
O2 C7 1.199(7) . ?
O4 H4C 0.8500 . ?
O4 H4D 0.8500 . ?
O3 C9 1.228(6) . ?
C7 C6 1.499(8) . ?
C9 C10 1.490(7) . ?
C10 C11 1.376(8) . ?
C10 C15 1.359(8) . ?
C6 H6 0.9800 . ?
C6 C5 1.530(8) . ?
C2 C1 1.485(9) . ?
C13 C12 1.385(10) . ?
C13 C14 1.366(11) . ?
C13 C16 1.448(10) . ?
C11 H11 0.9300 . ?
C11 C12 1.367(9) . ?
C12 H12 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.399(9) . ?
C14 H14 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.502(10) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.477(14) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
F1 C16 1.323(12) . ?
F3 C16 1.275(12) . ?
F2 C16 1.278(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 N2 H2 121.5 . . ?
C7 N2 H2 121.5 . . ?
C7 N2 N3 117.0(5) . . ?
C6 N1 C3 112.4(5) . . ?
C2 N1 C6 120.7(5) . . ?
C2 N1 C3 125.9(5) . . ?
N2 N3 C8 115.7(5) . . ?
C9 N3 N2 119.2(4) . . ?
C9 N3 C8 120.9(4) . . ?
H4C O4 H4D 104.5 . . ?
N2 C7 C6 115.5(5) . . ?
O2 C7 N2 122.6(5) . . ?
O2 C7 C6 121.4(6) . . ?
N3 C9 C10 118.3(5) . . ?
O3 C9 N3 121.0(5) . . ?
O3 C9 C10 120.7(5) . . ?
C11 C10 C9 122.0(5) . . ?
C15 C10 C9 119.0(6) . . ?
C15 C10 C11 118.9(5) . . ?
N1 C6 C7 115.0(5) . . ?
N1 C6 H6 108.7 . . ?
N1 C6 C5 103.8(5) . . ?
C7 C6 H6 108.7 . . ?
C7 C6 C5 111.6(5) . . ?
C5 C6 H6 108.7 . . ?
O1 C2 N1 120.4(5) . . ?
O1 C2 C1 122.0(6) . . ?
N1 C2 C1 117.6(6) . . ?
C12 C13 C16 120.0(8) . . ?
C14 C13 C12 119.4(6) . . ?
C14 C13 C16 120.6(8) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.9(6) . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 120.3(7) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C10 C15 H15 119.5 . . ?
C10 C15 C14 121.1(7) . . ?
C14 C15 H15 119.5 . . ?
C13 C14 C15 119.5(7) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
N1 C3 H3A 111.3 . . ?
N1 C3 H3B 111.3 . . ?
N1 C3 C4 102.4(6) . . ?
H3A C3 H3B 109.2 . . ?
C4 C3 H3A 111.3 . . ?
C4 C3 H3B 111.3 . . ?
C6 C5 H5A 110.9 . . ?
C6 C5 H5B 110.9 . . ?
H5A C5 H5B 108.9 . . ?
C4 C5 C6 104.4(6) . . ?
C4 C5 H5A 110.9 . . ?
C4 C5 H5B 110.9 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C4 C5 106.4(7) . . ?
C3 C4 H4A 110.5 . . ?
C3 C4 H4B 110.5 . . ?
C5 C4 H4A 110.5 . . ?
C5 C4 H4B 110.5 . . ?
H4A C4 H4B 108.6 . . ?
F1 C16 C13 114.9(9) . . ?
F3 C16 C13 113.6(10) . . ?
F3 C16 F1 102.6(9) . . ?
F3 C16 F2 106.3(10) . . ?
F2 C16 C13 115.8(8) . . ?
F2 C16 F1 102.2(10) . . ?

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
N2 N3 C9 O3 -163.5(6) . . . . ?
N2 N3 C9 C10 18.2(8) . . . . ?
N2 C7 C6 N1 -27.2(7) . . . . ?
N2 C7 C6 C5 90.7(6) . . . . ?
N1 C6 C5 C4 23.9(7) . . . . ?
N1 C3 C4 C5 28.8(8) . . . . ?
N3 N2 C7 O2 -7.6(8) . . . . ?
N3 N2 C7 C6 -180.0(4) . . . . ?
N3 C9 C10 C11 60.5(8) . . . . ?
N3 C9 C10 C15 -124.5(6) . . . . ?
O2 C7 C6 N1 160.3(5) . . . . ?
O2 C7 C6 C5 -81.8(8) . . . . ?
O3 C9 C10 C11 -117.8(7) . . . . ?
O3 C9 C10 C15 57.3(9) . . . . ?
C7 N2 N3 C9 70.5(7) . . . . ?
C7 N2 N3 C8 -86.7(6) . . . . ?
C7 C6 C5 C4 -100.5(7) . . . . ?
C9 C10 C11 C12 173.8(6) . . . . ?
C9 C10 C15 C14 -175.2(6) . . . . ?
C10 C11 C12 C13 1.9(10) . . . . ?
C10 C15 C14 C13 0.6(11) . . . . ?
C6 N1 C2 O1 6.8(8) . . . . ?
C6 N1 C2 C1 -173.0(6) . . . . ?
C6 N1 C3 C4 -13.6(8) . . . . ?
C6 C5 C4 C3 -33.2(8) . . . . ?
C2 N1 C6 C7 -74.3(7) . . . . ?
C2 N1 C6 C5 163.5(6) . . . . ?
C2 N1 C3 C4 177.4(7) . . . . ?
C11 C10 C15 C14 0.0(10) . . . . ?
C12 C13 C14 C15 0.1(11) . . . . ?
C12 C13 C16 F1 -174.1(9) . . . . ?
C12 C13 C16 F3 68.3(12) . . . . ?
C12 C13 C16 F2 -55.2(14) . . . . ?
C15 C10 C11 C12 -1.3(9) . . . . ?
C14 C13 C12 C11 -1.3(11) . . . . ?
C14 C13 C16 F1 8.4(13) . . . . ?
C14 C13 C16 F3 -109.3(12) . . . . ?
C14 C13 C16 F2 127.3(10) . . . . ?
C3 N1 C6 C7 116.0(6) . . . . ?
C3 N1 C6 C5 -6.2(6) . . . . ?
C3 N1 C2 O1 175.0(6) . . . . ?
C3 N1 C2 C1 -4.9(9) . . . . ?
C8 N3 C9 O3 -7.5(9) . . . . ?
C8 N3 C9 C10 174.2(6) . . . . ?
C16 C13 C12 C11 -178.9(8) . . . . ?
C16 C13 C14 C15 177.6(8) . . . . ?

_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_pro-c(o)-nh_nme-c(o)phOMe_a
_database_code_depnum_ccdc_archive 'CCDC 2240713'
loop_
_audit_author_name
_audit_author_address
'Jugal Kishore Rai Deka'
;Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR), Bangalore
India
;
_audit_update_record             
;
2023-02-08 deposited with the CCDC.	2023-04-20 downloaded from the CCDC.
;
_audit_creation_date             2023-02-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H21 N3 O4, 2(H2 O)'
_chemical_formula_sum            'C16 H25 N3 O6'
_chemical_formula_weight         355.39
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5736(9)
_cell_length_b                   8.7880(7)
_cell_length_c                   11.6294(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.122(4)
_cell_angle_gamma                90
_cell_volume                     939.94(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5334
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.84
_cell_measurement_theta_min      2.21
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            silver
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16661
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.513
_diffrn_reflns_theta_min         2.214
_diffrn_ambient_temperature      298.74
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.994
_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                   x-ray
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                3717
_reflns_number_total             5688
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.107
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 
;
 Flack x determined using 1330 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_coef       0.062(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         5688
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.021
_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)+(0.0412P)²+0.0625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.1053
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C4(H4a,H4b), C3(H3a,H3b)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C1(H1a,H1b,H1c), C16(H16a,H16b,H16c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O2 O 0.31512(17) 0.38863(18) 0.72002(16) 0.0628(5) Uani 1 1 d . . . . .
O3 O -0.12212(17) 0.5715(3) 0.53754(17) 0.0728(5) Uani 1 1 d . . . . .
N2 N 0.25321(19) 0.6260(2) 0.65303(17) 0.0515(4) Uani 1 1 d . . . . .
O5 O 0.6697(2) 0.4247(2) 0.3509(2) 0.0721(6) Uani 1 1 d . . . . .
O6 O 0.5399(3) 0.6260(2) 0.1773(2) 0.0768(6) Uani 1 1 d . . . . .
N3 N 0.10751(19) 0.6000(2) 0.64661(17) 0.0566(5) Uani 1 1 d . . . . .
O1 O 0.5290(2) 0.5885(2) 0.94164(16) 0.0799(6) Uani 1 1 d . . . . .
N1 N 0.60791(19) 0.4744(2) 0.80058(17) 0.0521(5) Uani 1 1 d . . . . .
O4 O 0.1367(2) 0.5039(3) 0.09918(18) 0.0795(6) Uani 1 1 d . . . . .
C7 C 0.3510(2) 0.5159(2) 0.69752(19) 0.0475(5) Uani 1 1 d . . . . .
C9 C 0.0074(2) 0.5774(3) 0.5404(2) 0.0545(5) Uani 1 1 d . . . . .
C6 C 0.5065(2) 0.5619(3) 0.70646(19) 0.0484(5) Uani 1 1 d . . . . .
H6 H 0.520228 0.671358 0.721532 0.058 Uiso 1 1 calc R U . . .
C14 C 0.0123(3) 0.6220(3) 0.2209(2) 0.0644(7) Uani 1 1 d . . . . .
H14 H -0.036298 0.679206 0.154552 0.077 Uiso 1 1 calc R U . . .
C2 C 0.6107(3) 0.4952(3) 0.9149(2) 0.0599(6) Uani 1 1 d . . . . .
C10 C 0.0540(2) 0.5606(3) 0.4296(2) 0.0509(5) Uani 1 1 d . . . . .
C15 C -0.0195(3) 0.6437(3) 0.3285(2) 0.0599(6) Uani 1 1 d . . . . .
H15 H -0.090219 0.713913 0.333686 0.072 Uiso 1 1 calc R U . . .
C11 C 0.1563(3) 0.4545(3) 0.4174(2) 0.0571(6) Uani 1 1 d . . . . .
H11 H 0.205488 0.397074 0.483362 0.068 Uiso 1 1 calc R U . . .
C12 C 0.1866(3) 0.4323(3) 0.3088(2) 0.0617(6) Uani 1 1 d . . . . .
H12 H 0.255238 0.360291 0.302504 0.074 Uiso 1 1 calc R U . . .
C13 C 0.1153(3) 0.5166(3) 0.2102(2) 0.0593(6) Uani 1 1 d . . . . .
C8 C 0.0681(3) 0.6122(4) 0.7583(2) 0.0757(8) Uani 1 1 d . . . . .
H8A H 0.066426 0.717466 0.779974 0.114 Uiso 1 1 calc R U . . .
H8B H 0.138294 0.558818 0.820248 0.114 Uiso 1 1 calc R U . . .
H8C H -0.026341 0.568434 0.748460 0.114 Uiso 1 1 calc R U . . .
C5 C 0.5501(3) 0.5165(3) 0.5939(3) 0.0686(7) Uani 1 1 d . . . . .
H5A H 0.466683 0.517137 0.523781 0.082 Uiso 1 1 calc R U . . .
H5B H 0.623786 0.584508 0.580394 0.082 Uiso 1 1 calc R U . . .
C4 C 0.6099(4) 0.3559(4) 0.6223(3) 0.0817(9) Uani 1 1 d . . . . .
H4A H 0.531774 0.281844 0.607557 0.098 Uiso 1 1 calc R U . . .
H4B H 0.674980 0.329645 0.574624 0.098 Uiso 1 1 calc R U . . .
C1 C 0.7136(4) 0.3982(4) 1.0074(3) 0.0874(10) Uani 1 1 d . . . . .
H1A H 0.723900 0.440280 1.085522 0.131 Uiso 1 1 calc R U . . .
H1B H 0.806776 0.395873 0.991552 0.131 Uiso 1 1 calc R U . . .
H1C H 0.675747 0.296672 1.004195 0.131 Uiso 1 1 calc R U . . .
C3 C 0.6902(3) 0.3628(3) 0.7531(3) 0.0707(7) Uani 1 1 d . . . . .
H3A H 0.690351 0.264456 0.791011 0.085 Uiso 1 1 calc R U . . .
H3B H 0.789857 0.395829 0.764694 0.085 Uiso 1 1 calc R U . . .
C16 C 0.2406(4) 0.3948(5) 0.0834(3) 0.0918(10) Uani 1 1 d . . . . .
H16A H 0.333963 0.416842 0.137697 0.138 Uiso 1 1 calc R U . . .
H16B H 0.247204 0.399545 0.002568 0.138 Uiso 1 1 calc R U . . .
H16C H 0.210500 0.294598 0.099248 0.138 Uiso 1 1 calc R U . . .
H50 H 0.280(3) 0.720(3) 0.651(2) 0.053(7) Uiso 1 1 d . . . . .
H51 H 0.741(4) 0.477(4) 0.398(3) 0.086(10) Uiso 1 1 d . . . . .
H52 H 0.633(4) 0.486(5) 0.290(3) 0.090(11) Uiso 1 1 d . . . . .
H53 H 0.546(4) 0.616(6) 0.098(4) 0.123(14) Uiso 1 1 d . . . . .
H54 H 0.584(5) 0.717(6) 0.198(4) 0.117(14) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C7 1.220(3) . ?
O3 C9 1.232(3) . ?
N2 N3 1.395(3) . ?
N2 C7 1.346(3) . ?
N3 C9 1.352(3) . ?
N3 C8 1.454(3) . ?
O1 C2 1.231(3) . ?
N1 C6 1.463(3) . ?
N1 C2 1.335(3) . ?
N1 C3 1.459(3) . ?
O4 C13 1.366(3) . ?
O4 C16 1.431(4) . ?
C7 C6 1.518(3) . ?
C9 C10 1.484(3) . ?
C6 C5 1.534(3) . ?
C14 C15 1.381(4) . ?
C14 C13 1.384(4) . ?
C2 C1 1.505(4) . ?
C10 C15 1.397(3) . ?
C10 C11 1.388(3) . ?
C11 C12 1.385(4) . ?
C12 C13 1.376(3) . ?
C5 C4 1.524(4) . ?
C4 C3 1.503(5) . ?

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
C7 N2 N3 118.8(2) . . ?
N2 N3 C8 116.34(18) . . ?
C9 N3 N2 121.2(2) . . ?
C9 N3 C8 122.2(2) . . ?
C2 N1 C6 119.95(19) . . ?
C2 N1 C3 127.2(2) . . ?
C3 N1 C6 112.7(2) . . ?
C13 O4 C16 117.9(2) . . ?
O2 C7 N2 122.3(2) . . ?
O2 C7 C6 124.0(2) . . ?
N2 C7 C6 113.53(19) . . ?
O3 C9 N3 118.9(2) . . ?
O3 C9 C10 121.1(2) . . ?
N3 C9 C10 120.00(19) . . ?
N1 C6 C7 110.22(18) . . ?
N1 C6 C5 102.74(19) . . ?
C7 C6 C5 111.50(19) . . ?
C15 C14 C13 121.1(2) . . ?
O1 C2 N1 120.2(2) . . ?
O1 C2 C1 122.1(3) . . ?
N1 C2 C1 117.6(2) . . ?
C15 C10 C9 118.4(2) . . ?
C11 C10 C9 123.2(2) . . ?
C11 C10 C15 118.0(2) . . ?
C14 C15 C10 120.3(2) . . ?
C12 C11 C10 121.3(2) . . ?
C13 C12 C11 120.2(2) . . ?
O4 C13 C14 115.9(2) . . ?
O4 C13 C12 125.0(3) . . ?
C12 C13 C14 119.1(2) . . ?
C4 C5 C6 103.3(2) . . ?
C3 C4 C5 103.8(2) . . ?
N1 C3 C4 103.4(2) . . ?

_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_pro-c(o)-nh_nme-c(o)ph_a
_database_code_depnum_ccdc_archive 'CCDC 2239866'
loop_
_audit_author_name
_audit_author_address
'Jugal Kishore Rai Deka'
;Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR), Bangalore
India
;
_audit_update_record             
;
2023-02-04 deposited with the CCDC.	2023-04-20 downloaded from the CCDC.
;
_audit_creation_date             2023-02-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_formula_moiety         'C15 H19 N3 O3'
_chemical_formula_sum            'C15 H19 N3 O3'
_chemical_formula_weight         289.336
_chemical_absolute_configuration ad
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   8.3640(3)
_cell_length_b                   10.6149(5)
_cell_length_c                   17.5618(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1559.19(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    299.99
_cell_measurement_reflns_used    3136
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      21.48

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.8947
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             616.423
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.057
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.9969
_diffrn_reflns_Laue_measured_fraction_max 0.9973
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16192
_diffrn_reflns_point_group_measured_fraction_full 0.9979
_diffrn_reflns_point_group_measured_fraction_max 0.9978
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         2.24
_diffrn_ambient_temperature      299.99
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9973
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   X-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_reflns_Friedel_coverage         0.999
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                2219
_reflns_number_total             3195
_reflns_threshold_expression     I>=2u(I)
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.1808
_refine_diff_density_min         -0.1588
_refine_diff_density_rms         0.0412
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.3(8)
_refine_ls_d_res_high            0.7996
_refine_ls_d_res_low             9.0844
_refine_ls_extinction_coef       0.030(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.1213
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    29
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.1213
_refine_ls_shift/su_max          0.0108
_refine_ls_shift/su_mean         0.0004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0468P)²+0.0640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.1141
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C5(H5a,H5b), C4(H4a,H4b)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C12(H12), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C1(H1a,H1b,H1c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O3 O 0.65890(19) 0.40230(19) 0.20070(9) 0.0821(6) Uani 1.000000 .
O2 O 0.51116(19) 0.51782(16) 0.38829(9) 0.0689(5) Uani 1.000000 .
N2 N 0.6205(2) 0.3239(2) 0.39097(10) 0.0544(5) Uani 1.000000 .
O1 O 0.3023(2) 0.36156(18) 0.53792(10) 0.0754(5) Uani 1.000000 .
N3 N 0.6129(2) 0.30841(19) 0.31240(10) 0.0570(5) Uani 1.000000 .
N1 N 0.4861(2) 0.51193(18) 0.54851(11) 0.0572(5) Uani 1.000000 .
C7 C 0.5695(2) 0.4312(2) 0.42374(12) 0.0529(6) Uani 1.000000 .
C9 C 0.6996(2) 0.3861(2) 0.26661(13) 0.0527(6) Uani 1.000000 .
C11 C 0.9538(2) 0.3806(2) 0.34556(13) 0.0564(6) Uani 1.000000 .
H11 H 0.9261(2) 0.3022(2) 0.36510(13) 0.0677(7) Uiso 1.000000 R
C10 C 0.8507(2) 0.4425(2) 0.29650(12) 0.0497(5) Uani 1.000000 .
C15 C 0.8960(3) 0.5576(2) 0.26788(15) 0.0678(7) Uani 1.000000 .
H15 H 0.8295(3) 0.5997(2) 0.23388(15) 0.0814(8) Uiso 1.000000 R
C2 C 0.3409(3) 0.4673(3) 0.56223(13) 0.0596(6) Uani 1.000000 .
C12 C 1.0977(3) 0.4353(3) 0.36554(14) 0.0677(7) Uani 1.000000 .
H12 H 1.1660(3) 0.3935(3) 0.39881(14) 0.0812(8) Uiso 1.000000 R
C6 C 0.6045(3) 0.4368(3) 0.50837(12) 0.0602(6) Uani 1.000000 .
H6 H 0.6106(3) 0.3518(3) 0.52995(12) 0.0722(8) Uiso 1.000000 R
C8 C 0.4666(3) 0.2506(3) 0.28353(15) 0.0797(8) Uani 1.000000 .
H8a H 0.3807(6) 0.3105(7) 0.2861(10) 0.1196(12) Uiso 1.000000 GR
H8b H 0.4823(8) 0.2251(17) 0.2316(4) 0.1196(12) Uiso 1.000000 GR
H8c H 0.4405(13) 0.1783(11) 0.3139(7) 0.1196(12) Uiso 1.000000 GR
C13 C 1.1407(3) 0.5497(3) 0.33710(16) 0.0779(8) Uani 1.000000 .
H13 H 1.2384(3) 0.5854(3) 0.35024(16) 0.0935(9) Uiso 1.000000 R
C14 C 1.0392(3) 0.6112(3) 0.28919(19) 0.0875(9) Uani 1.000000 .
H14 H 1.0669(3) 0.6904(3) 0.27066(19) 0.1050(10) Uiso 1.000000 R
C3 C 0.5490(3) 0.6351(3) 0.57113(17) 0.0817(8) Uani 1.000000 .
H3a H 0.4777(3) 0.7024(3) 0.55553(17) 0.0981(10) Uiso 1.000000 R
H3b H 0.5646(3) 0.6395(3) 0.62580(17) 0.0981(10) Uiso 1.000000 R
C5 C 0.7586(3) 0.5097(4) 0.52400(16) 0.0997(12) Uani 1.000000 .
H5a H 0.8079(3) 0.4819(4) 0.57111(16) 0.1196(14) Uiso 1.000000 R
H5b H 0.8344(3) 0.4990(4) 0.48269(16) 0.1196(14) Uiso 1.000000 R
C1 C 0.2286(4) 0.5453(3) 0.60937(19) 0.1013(11) Uani 1.000000 .
H1a H 0.1241(8) 0.5078(13) 0.6086(11) 0.1519(16) Uiso 1.000000 GR
H1b H 0.2668(15) 0.5490(19) 0.6609(4) 0.1519(16) Uiso 1.000000 GR
H1c H 0.223(2) 0.6290(7) 0.5888(8) 0.1519(16) Uiso 1.000000 GR
C4 C 0.7055(4) 0.6429(4) 0.52981(18) 0.1060(12) Uani 1.000000 .
H4a H 0.6917(4) 0.6799(4) 0.47971(18) 0.1272(14) Uiso 1.000000 R
H4b H 0.7821(4) 0.6928(4) 0.55826(18) 0.1272(14) Uiso 1.000000 R
H2 H 0.666(3) 0.264(2) 0.4190(13) 0.065(7) Uiso 1.000000 .


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 C9 1.219(2) . ?
O2 C7 1.213(2) . ?
N2 N3 1.391(2) . ?
N2 C7 1.345(3) . ?
N2 H2 0.89(2) . ?
O1 C2 1.243(3) . ?
N3 C9 1.361(3) . ?
N3 C8 1.460(3) . ?
N1 C2 1.326(3) . ?
N1 C6 1.454(3) . ?
N1 C3 1.464(3) . ?
C7 C6 1.516(3) . ?
C9 C10 1.494(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.384(3) . ?
C11 C12 1.381(3) . ?
C10 C15 1.375(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.378(3) . ?
C2 C1 1.501(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.361(4) . ?
C6 H6 0.9800 . ?
C6 C5 1.528(4) . ?
C8 H8a 0.9600 . ?
C8 H8b 0.9600 . ?
C8 H8c 0.9600 . ?
C13 H13 0.9300 . ?
C13 C14 1.362(4) . ?
C14 H14 0.9300 . ?
C3 H3a 0.9700 . ?
C3 H3b 0.9700 . ?
C3 C4 1.499(4) . ?
C5 H5a 0.9700 . ?
C5 H5b 0.9700 . ?
C5 C4 1.486(5) . ?
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 0.9600 . ?
C4 H4a 0.9700 . ?
C4 H4b 0.9700 . ?

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
C7 N2 N3 120.69(19) . . ?
H2 N2 N3 118.8(14) . . ?
H2 N2 C7 120.4(14) . . ?
C9 N3 N2 119.35(18) . . ?
C8 N3 N2 115.63(18) . . ?
C8 N3 C9 119.72(19) . . ?
C6 N1 C2 121.0(2) . . ?
C3 N1 C2 126.8(2) . . ?
C3 N1 C6 112.14(19) . . ?
N2 C7 O2 123.3(2) . . ?
C6 C7 O2 123.4(2) . . ?
C6 C7 N2 113.1(2) . . ?
N3 C9 O3 119.9(2) . . ?
C10 C9 O3 120.9(2) . . ?
C10 C9 N3 119.07(18) . . ?
C10 C11 H11 119.96(13) . . ?
C12 C11 H11 119.96(15) . . ?
C12 C11 C10 120.1(2) . . ?
C11 C10 C9 123.7(2) . . ?
C15 C10 C9 117.5(2) . . ?
C15 C10 C11 118.5(2) . . ?
H15 C15 C10 119.76(13) . . ?
C14 C15 C10 120.5(2) . . ?
C14 C15 H15 119.76(17) . . ?
N1 C2 O1 119.9(2) . . ?
C1 C2 O1 121.7(2) . . ?
C1 C2 N1 118.4(2) . . ?
H12 C12 C11 119.61(15) . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.61(15) . . ?
C7 C6 N1 111.44(18) . . ?
H6 C6 N1 110.68(12) . . ?
H6 C6 C7 110.68(14) . . ?
C5 C6 N1 102.1(2) . . ?
C5 C6 C7 111.0(2) . . ?
C5 C6 H6 110.68(18) . . ?
H8a C8 N3 109.5 . . ?
H8b C8 N3 109.5 . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 N3 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
H13 C13 C12 120.33(15) . . ?
C14 C13 C12 119.3(2) . . ?
C14 C13 H13 120.33(16) . . ?
C13 C14 C15 120.7(3) . . ?
H14 C14 C15 119.63(17) . . ?
H14 C14 C13 119.63(16) . . ?
H3a C3 N1 111.08(13) . . ?
H3b C3 N1 111.08(14) . . ?
H3b C3 H3a 109.0 . . ?
C4 C3 N1 103.4(2) . . ?
C4 C3 H3a 111.1(2) . . ?
C4 C3 H3b 111.08(16) . . ?
H5a C5 C6 110.95(16) . . ?
H5b C5 C6 110.95(13) . . ?
H5b C5 H5a 109.0 . . ?
C4 C5 C6 104.0(2) . . ?
C4 C5 H5a 110.95(18) . . ?
C4 C5 H5b 110.95(18) . . ?
H1a C1 C2 109.5 . . ?
H1b C1 C2 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 C2 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
C5 C4 C3 104.0(3) . . ?
H4a C4 C3 110.97(18) . . ?
H4a C4 C5 110.97(18) . . ?
H4b C4 C3 110.97(17) . . ?
H4b C4 C5 110.97(17) . . ?
H4b C4 H4a 109.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C9 N3 N2 -156.6(2) . . . . ?
O3 C9 N3 C8 -3.5(3) . . . . ?
O3 C9 C10 C11 -140.0(2) . . . . ?
O3 C9 C10 C15 33.8(3) . . . . ?
O2 C7 N2 N3 2.0(2) . . . . ?
O2 C7 C6 N1 34.2(2) . . . . ?
O2 C7 C6 C5 -78.9(3) . . . . ?
N2 N3 C9 C10 28.0(2) . . . . ?
N2 C7 C6 N1 -150.39(19) . . . . ?
N2 C7 C6 C5 96.5(2) . . . . ?
O1 C2 N1 C6 -2.9(3) . . . . ?
O1 C2 N1 C3 178.3(2) . . . . ?
N3 C9 C10 C11 35.3(3) . . . . ?
N3 C9 C10 C15 -150.9(2) . . . . ?
N1 C6 C5 C4 -31.4(2) . . . . ?
N1 C3 C4 C5 -30.0(2) . . . . ?
C7 C6 C5 C4 87.5(3) . . . . ?
C9 C10 C11 C12 174.6(2) . . . . ?
C9 C10 C15 C14 -175.7(2) . . . . ?
C11 C10 C15 C14 -1.6(3) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C10 C15 C14 C13 2.0(3) . . . . ?
C15 C14 C13 C12 -1.6(4) . . . . ?
C6 C5 C4 C3 38.6(2) . . . . ?


_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_pro_c(o)-nh_nme-c(o)phCN_a
_database_code_depnum_ccdc_archive 'CCDC 2240910'
loop_
_audit_author_name
_audit_author_address
'Jugal Kishore Rai Deka'
;Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR), Bangalore
India
;
_audit_update_record             
;
2023-02-09 deposited with the CCDC.	2023-04-20 downloaded from the CCDC.
;
_audit_creation_date             2023-02-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_formula_moiety         'C16 H18 N4 O3'
_chemical_formula_sum            'C16 H18 N4 O3'
_chemical_formula_weight         314.346
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   6.8839(4)
_cell_length_b                   14.6506(11)
_cell_length_c                   16.5975(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1673.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297.42
_cell_measurement_reflns_used    3151
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      21.10

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6740
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             664.464
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.023
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 0.9983
_diffrn_reflns_Laue_measured_fraction_max 0.9973
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19160
_diffrn_reflns_point_group_measured_fraction_full 0.9987
_diffrn_reflns_point_group_measured_fraction_max 0.9889
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         30.54
_diffrn_reflns_theta_min         2.78
_diffrn_ambient_temperature      297.42
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9973
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   X-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_reflns_Friedel_coverage         0.978
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              20
_reflns_limit_k_min              -20
_reflns_limit_l_max              23
_reflns_limit_l_min              -23
_reflns_number_gt                2099
_reflns_number_total             5060
_reflns_threshold_expression     I>=2u(I)
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.2595
_refine_diff_density_min         -0.2269
_refine_diff_density_rms         0.0606
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   -0.7(9)
_refine_ls_d_res_high            0.6994
_refine_ls_d_res_low             7.3253
_refine_ls_extinction_coef       0.045(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.1442
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    44
_refine_ls_number_parameters     221
_refine_ls_number_reflns         5060
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1563
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.1442
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0763P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1990
_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. Uiso/Uaniso restraints and constraints
Uanis(C3a) = Uanis(C3b)
Uanis(C4a) = Uanis(C4b)
Uanis(C5a) = Uanis(C5b)
3. Others
 Sof(H6b)=Sof(C5b)=Sof(H5ba)=Sof(H5bb)=Sof(C3b)=Sof(H3ba)=Sof(H3bb)=Sof(C4b)=
 Sof(H4ba)=Sof(H4bb)=1-FVAR(1)
 Sof(H6a)=Sof(C3a)=Sof(H3aa)=Sof(H3ab)=Sof(C4a)=Sof(H4aa)=Sof(H4ab)=Sof(C5a)=
 Sof(H5aa)=Sof(H5ab)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C6(H6a), C6(H6b)
4.b Secondary CH2 refined with riding coordinates:
 C3a(H3aa,H3ab), C4a(H4aa,H4ab), C5a(H5aa,H5ab), C5b(H5ba,H5bb), C3b(H3ba,
 H3bb), C4b(H4ba,H4bb)
4.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C14(H14), C15(H15), C11(H11), C12(H12)
4.d Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C1(H1a,H1b,H1c)
;
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_refinement_flags_posn
_atom_site_disorder_group
O3 O -0.0831(3) 0.40155(15) 0.36177(14) 0.0882(7) Uani 1.000000 . .
O2 O -0.1139(4) 0.55294(16) 0.55270(12) 0.0863(7) Uani 1.000000 . .
O1 O -0.1243(4) 0.78736(17) 0.59439(15) 0.0958(8) Uani 1.000000 . .
N2 N 0.0771(3) 0.60267(15) 0.45152(14) 0.0668(7) Uani 1.000000 . .
H2 H 0.1679(3) 0.63956(15) 0.43717(14) 0.0801(8) Uiso 1.000000 R .
N3 N -0.0086(3) 0.54608(16) 0.39451(13) 0.0663(6) Uani 1.000000 . .
C9 C 0.0203(4) 0.4544(2) 0.39886(16) 0.0624(7) Uani 1.000000 . .
C10 C 0.1846(4) 0.42163(18) 0.45034(16) 0.0589(7) Uani 1.000000 . .
N1 N 0.0413(4) 0.68136(18) 0.65746(15) 0.0844(9) Uani 1.000000 . .
C14 C 0.2916(5) 0.3266(2) 0.55796(18) 0.0735(8) Uani 1.000000 . .
H14 H 0.2644(5) 0.2832(2) 0.59728(18) 0.0882(10) Uiso 1.000000 R .
C13 C 0.4790(5) 0.3600(2) 0.54942(17) 0.0681(8) Uani 1.000000 . .
C15 C 0.1468(4) 0.35752(19) 0.50851(17) 0.0681(8) Uani 1.000000 . .
H15 H 0.0214(4) 0.33484(19) 0.51440(17) 0.0818(9) Uiso 1.000000 R .
C7 C 0.0193(5) 0.6003(2) 0.52916(19) 0.0679(8) Uani 1.000000 . .
C2 C -0.0915(5) 0.7456(2) 0.6571(2) 0.0765(9) Uani 1.000000 . .
C11 C 0.3733(4) 0.4525(2) 0.43990(17) 0.0692(8) Uani 1.000000 . .
H11 H 0.4013(4) 0.4940(2) 0.39914(17) 0.0831(9) Uiso 1.000000 R .
N4 N 0.7468(5) 0.3127(2) 0.6491(2) 0.1119(11) Uani 1.000000 . .
C12 C 0.5193(5) 0.4220(2) 0.4895(2) 0.0745(8) Uani 1.000000 . .
H12 H 0.6455(5) 0.4433(2) 0.4826(2) 0.0894(10) Uiso 1.000000 R .
C16 C 0.6305(5) 0.3333(2) 0.6045(2) 0.0820(9) Uani 1.000000 . .
C8 C -0.1720(5) 0.5843(3) 0.3513(2) 0.0885(10) Uani 1.000000 . .
H8a H -0.223(2) 0.5395(6) 0.3147(11) 0.1327(15) Uiso 1.000000 GR .
H8b H -0.2712(15) 0.6017(15) 0.3889(2) 0.1327(15) Uiso 1.000000 GR .
H8c H -0.1303(9) 0.6370(10) 0.3216(11) 0.1327(15) Uiso 1.000000 GR .
C6 C 0.1444(5) 0.6572(2) 0.5846(2) 0.0819(10) Uani 1.000000 . .
H6a H 0.1573(5) 0.7154(2) 0.5560(2) 0.0983(12) Uiso 0.385(11) R 1
H6b H 0.2062(5) 0.7093(2) 0.5579(2) 0.0983(12) Uiso 0.615(11) R 2
C1 C -0.1941(7) 0.7678(4) 0.7338(2) 0.1227(16) Uani 1.000000 . .
H1a H -0.284(4) 0.8170(16) 0.7248(5) 0.184(2) Uiso 1.000000 GR .
H1b H -0.264(4) 0.7151(8) 0.7523(11) 0.184(2) Uiso 1.000000 GR .
H1c H -0.1008(8) 0.786(2) 0.7739(7) 0.184(2) Uiso 1.000000 GR .
C3a C 0.164(3) 0.629(2) 0.7180(17) 0.110(5) Uani 0.385(11) . 1
H3aa H 0.229(3) 0.672(2) 0.7538(17) 0.133(5) Uiso 0.385(11) R 1
H3ab H 0.082(3) 0.590(2) 0.7502(17) 0.133(5) Uiso 0.385(11) R 1
C4a C 0.304(4) 0.5763(15) 0.6756(15) 0.146(5) Uani 0.385(11) . 1
H4aa H 0.420(4) 0.5691(15) 0.7085(15) 0.175(6) Uiso 0.385(11) R 1
H4ab H 0.252(4) 0.5161(15) 0.6648(15) 0.175(6) Uiso 0.385(11) R 1
C5a C 0.360(3) 0.6235(14) 0.5944(11) 0.106(4) Uani 0.385(11) . 1
H5aa H 0.401(3) 0.5812(14) 0.5528(11) 0.127(4) Uiso 0.385(11) R 1
H5ab H 0.453(3) 0.6727(14) 0.6004(11) 0.127(4) Uiso 0.385(11) R 1
C5b C 0.2950(14) 0.5901(8) 0.6283(8) 0.106(4) Uani 0.615(11) . 2
H5ba H 0.3367(14) 0.5425(8) 0.5917(8) 0.127(4) Uiso 0.615(11) R 2
H5bb H 0.4085(14) 0.6237(8) 0.6463(8) 0.127(4) Uiso 0.615(11) R 2
C3b C 0.0624(18) 0.6227(12) 0.7311(10) 0.110(5) Uani 0.615(11) . 2
H3ba H 0.1246(18) 0.6557(12) 0.7747(10) 0.133(5) Uiso 0.615(11) R 2
H3bb H -0.0624(18) 0.5999(12) 0.7493(10) 0.133(5) Uiso 0.615(11) R 2
C4b C 0.186(2) 0.5485(8) 0.7012(8) 0.146(5) Uani 0.615(11) . 2
H4ba H 0.108(2) 0.4966(8) 0.6847(8) 0.175(6) Uiso 0.615(11) R 2
H4bb H 0.277(2) 0.5289(8) 0.7424(8) 0.175(6) Uiso 0.615(11) R 2


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 C9 1.219(3) . ?
O2 C7 1.215(4) . ?
O1 C2 1.228(3) . ?
N2 H2 0.8600 . ?
N2 N3 1.390(3) . ?
N2 C7 1.349(4) . ?
N3 C9 1.359(4) . ?
N3 C8 1.447(4) . ?
C9 C10 1.497(4) . ?
C10 C15 1.372(4) . ?
C10 C11 1.386(4) . ?
N1 C2 1.312(4) . ?
N1 C6 1.446(4) . ?
N1 C3a 1.52(3) . ?
N1 C3b 1.501(16) . ?
C14 H14 0.9300 . ?
C14 C13 1.387(5) . ?
C14 C15 1.369(4) . ?
C13 C12 1.375(4) . ?
C13 C16 1.440(5) . ?
C15 H15 0.9300 . ?
C7 C6 1.511(4) . ?
C2 C1 1.492(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(4) . ?
N4 C16 1.131(4) . ?
C12 H12 0.9300 . ?
C8 H8a 0.9600 . ?
C8 H8b 0.9600 . ?
C8 H8c 0.9600 . ?
C6 H6a 0.9800 . ?
C6 H6b 0.9800 . ?
C6 C5a 1.571(18) . ?
C6 C5b 1.602(11) . ?
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 0.9600 . ?
C3a H3aa 0.9700 . ?
C3a H3ab 0.9700 . ?
C3a C4a 1.42(4) . ?
C4a H4aa 0.9700 . ?
C4a H4ab 0.9700 . ?
C4a C5a 1.56(3) . ?
C5a H5aa 0.9700 . ?
C5a H5ab 0.9700 . ?
C5b H5ba 0.9700 . ?
C5b H5bb 0.9700 . ?
C5b C4b 1.548(14) . ?
C3b H3ba 0.9700 . ?
C3b H3bb 0.9700 . ?
C3b C4b 1.47(2) . ?
C4b H4ba 0.9700 . ?
C4b H4bb 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 N2 H2 119.68(14) . . ?
C7 N2 H2 119.68(16) . . ?
C7 N2 N3 120.6(2) . . ?
C9 N3 N2 119.4(2) . . ?
C8 N3 N2 115.9(2) . . ?
C8 N3 C9 121.5(3) . . ?
N3 C9 O3 121.0(3) . . ?
C10 C9 O3 121.7(3) . . ?
C10 C9 N3 117.2(2) . . ?
C15 C10 C9 118.5(2) . . ?
C11 C10 C9 122.2(2) . . ?
C11 C10 C15 119.3(3) . . ?
C6 N1 C2 120.9(3) . . ?
C3a N1 C2 138.7(12) . . ?
C3a N1 C6 99.0(11) . . ?
C3b N1 C2 118.8(7) . . ?
C3b N1 C6 119.5(7) . . ?
C3b N1 C3a 28.4(9) . . ?
C13 C14 H14 120.01(18) . . ?
C15 C14 H14 120.01(17) . . ?
C15 C14 C13 120.0(3) . . ?
C12 C13 C14 119.6(3) . . ?
C16 C13 C14 120.8(3) . . ?
C16 C13 C12 119.5(3) . . ?
C14 C15 C10 120.7(3) . . ?
H15 C15 C10 119.66(16) . . ?
H15 C15 C14 119.66(17) . . ?
N2 C7 O2 123.0(3) . . ?
C6 C7 O2 123.3(3) . . ?
C6 C7 N2 113.6(3) . . ?
N1 C2 O1 119.3(3) . . ?
C1 C2 O1 121.9(3) . . ?
C1 C2 N1 118.8(3) . . ?
H11 C11 C10 119.87(17) . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.87(17) . . ?
C11 C12 C13 120.1(3) . . ?
H12 C12 C13 119.96(19) . . ?
H12 C12 C11 119.96(17) . . ?
N4 C16 C13 178.5(3) . . ?
H8a C8 N3 109.5 . . ?
H8b C8 N3 109.5 . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 N3 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
C7 C6 N1 111.4(3) . . ?
H6a C6 N1 103.70(18) . . ?
H6a C6 C7 103.70(18) . . ?
H6b C6 N1 113.66(17) . . ?
H6b C6 C7 113.66(19) . . ?
H6b C6 H6a 20.5 . . ?
C5a C6 N1 117.0(7) . . ?
C5a C6 C7 115.3(8) . . ?
C5a C6 H6a 103.7(7) . . ?
C5a C6 H6b 83.2(7) . . ?
C5b C6 N1 95.1(5) . . ?
C5b C6 C7 107.8(4) . . ?
C5b C6 H6a 133.9(5) . . ?
C5b C6 H6b 113.7(5) . . ?
C5b C6 C5a 31.8(6) . . ?
H1a C1 C2 109.5 . . ?
H1b C1 C2 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 C2 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
H3aa C3a N1 109.9(12) . . ?
H3ab C3a N1 109.9(9) . . ?
H3ab C3a H3aa 108.301516581(15) . . ?
C4a C3a N1 109(2) . . ?
C4a C3a H3aa 109.9(15) . . ?
C4a C3a H3ab 109.9(14) . . ?
H4aa C4a C3a 109.6(15) . . ?
H4ab C4a C3a 109.6(14) . . ?
H4ab C4a H4aa 108.1 . . ?
C5a C4a C3a 110(2) . . ?
C5a C4a H4aa 109.6(11) . . ?
C5a C4a H4ab 109.6(11) . . ?
C4a C5a C6 89.9(13) . . ?
H5aa C5a C6 113.7(7) . . ?
H5aa C5a C4a 113.7(12) . . ?
H5ab C5a C6 113.7(8) . . ?
H5ab C5a C4a 113.7(11) . . ?
H5ab C5a H5aa 110.9 . . ?
H5ba C5b C6 110.4(4) . . ?
H5bb C5b C6 110.4(4) . . ?
H5bb C5b H5ba 108.6 . . ?
C4b C5b C6 106.4(7) . . ?
C4b C5b H5ba 110.4(6) . . ?
C4b C5b H5bb 110.4(6) . . ?
H3ba C3b N1 111.4(7) . . ?
H3bb C3b N1 111.4(5) . . ?
H3bb C3b H3ba 109.255851464(17) . . ?
C4b C3b N1 101.9(11) . . ?
C4b C3b H3ba 111.4(8) . . ?
C4b C3b H3bb 111.4(7) . . ?
C3b C4b C5b 104.6(9) . . ?
H4ba C4b C5b 110.8(6) . . ?
H4ba C4b C3b 110.8(7) . . ?
H4bb C4b C5b 110.8(6) . . ?
H4bb C4b C3b 110.8(8) . . ?
H4bb C4b H4ba 108.9 . . ?

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
O3 C9 N3 N2 164.1(3) . . . . ?
O3 C9 N3 C8 5.2(3) . . . . ?
O3 C9 C10 C15 -53.8(3) . . . . ?
O3 C9 C10 C11 124.8(3) . . . . ?
O2 C7 N2 N3 -3.5(4) . . . . ?
O2 C7 C6 N1 -25.8(3) . . . . ?
O2 C7 C6 C5a 110.6(8) . . . . ?
O2 C7 C6 C5b 77.3(6) . . . . ?
O1 C2 N1 C6 -2.0(4) . . . . ?
O1 C2 N1 C3a 161.3(14) . . . . ?
O1 C2 N1 C3b -172.2(7) . . . . ?
N2 N3 C9 C10 -16.4(3) . . . . ?
N2 C7 C6 N1 158.0(3) . . . . ?
N2 C7 C6 C5a -65.6(8) . . . . ?
N2 C7 C6 C5b -98.9(5) . . . . ?
N3 C9 C10 C15 126.7(3) . . . . ?
N3 C9 C10 C11 -54.6(3) . . . . ?
C9 C10 C15 C14 -178.9(2) . . . . ?
C9 C10 C11 C12 178.7(3) . . . . ?
C10 C15 C14 C13 -0.1(3) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
N1 C6 C5a C4a 34.8(10) . . . . ?
N1 C6 C5b C4b 30.9(6) . . . . ?
N1 C3a C4a C5a 29.6(19) . . . . ?
N1 C3b C4b C5b 23.7(9) . . . . ?
C14 C13 C12 C11 1.8(3) . . . . ?
C7 C6 C5a C4a -99.1(13) . . . . ?
C7 C6 C5b C4b -83.5(6) . . . . ?
C6 C5a C4a C3a -35.9(17) . . . . ?
C6 C5b C4b C3b -36.2(9) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
