# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 2212205'
loop_
_audit_author_name
_audit_author_address
'MANJEET SINGH'
;IISER PUNE
India
;
_audit_update_record             
;
2022-10-11 deposited with the CCDC.	2023-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C16
_chemical_formula_sum            'C16 H16 F5 N O4'
_chemical_formula_weight         381.30

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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'

_cell_length_a                   6.2002(9)
_cell_length_b                   9.3687(12)
_cell_length_c                   15.799(2)
_cell_angle_alpha                101.093(4)
_cell_angle_beta                 99.079(4)
_cell_angle_gamma                105.428(4)
_cell_volume                     846.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8242
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      24.75

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             392.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.142
_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            16604
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.327
_diffrn_reflns_theta_max         24.827
_diffrn_reflns_theta_full        24.827
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             5740
_reflns_number_gt                4921
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.976
_reflns_Friedel_fraction_max     0.971
_reflns_Friedel_fraction_full    0.971

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0273P)²+0.0724P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2104 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5740
_refine_ls_number_parameters     478
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0673
_refine_ls_wR_factor_gt          0.0631
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
F10 F 0.9757(3) 0.4099(2) 0.14982(13) 0.0297(5) Uani 1 1 d . . . . .
F4 F 0.3900(4) 0.8224(2) 1.13695(13) 0.0395(6) Uani 1 1 d . . . . .
F3 F 0.0075(4) 0.6134(2) 1.02718(15) 0.0384(6) Uani 1 1 d . . . . .
O1 O 0.2163(3) 0.1794(2) 0.40571(14) 0.0172(5) Uani 1 1 d . . . . .
F2 F 0.0222(3) 0.4809(2) 0.86067(14) 0.0366(6) Uani 1 1 d . . . . .
F1 F 0.7998(3) 0.7637(2) 0.91394(13) 0.0344(5) Uani 1 1 d . . . . .
F9 F 1.0964(4) 0.3166(2) -0.00333(15) 0.0401(6) Uani 1 1 d . . . . .
O5 O 0.7623(4) 0.8461(2) 0.57839(14) 0.0185(5) Uani 1 1 d . . . . .
O6 O 0.6674(4) 0.5863(2) 0.53442(15) 0.0209(5) Uani 1 1 d . . . . .
O4 O 0.4182(4) 0.5567(2) 0.79888(14) 0.0234(6) Uani 1 1 d . . . . .
F5 F 0.7843(4) 0.8982(2) 1.07934(14) 0.0407(6) Uani 1 1 d . . . . .
O8 O 0.5395(4) 0.2821(2) 0.17365(15) 0.0243(6) Uani 1 1 d . . . . .
F7 F 0.2315(3) 0.0672(2) 0.03493(16) 0.0401(6) Uani 1 1 d . . . . .
O2 O 0.3362(4) 0.0030(2) 0.46479(15) 0.0202(5) Uani 1 1 d . . . . .
F6 F 0.3534(4) -0.0254(2) -0.11914(15) 0.0512(7) Uani 1 1 d . . . . .
O7 O 0.5630(4) 0.5201(2) 0.15573(16) 0.0267(6) Uani 1 1 d . . . . .
O3 O 0.5128(4) 0.3631(3) 0.84500(16) 0.0296(6) Uani 1 1 d . . . . .
F8 F 0.7834(5) 0.0993(3) -0.13869(14) 0.0521(7) Uani 1 1 d . . . . .
N2 N 0.4616(4) 0.7188(3) 0.46929(17) 0.0163(6) Uani 1 1 d . . . . .
H2 H 0.441666 0.806728 0.471519 0.020 Uiso 1 1 calc R U . . .
N1 N 0.5277(4) 0.2565(3) 0.51377(17) 0.0178(6) Uani 1 1 d . . . . .
H1 H 0.541862 0.345253 0.503780 0.021 Uiso 1 1 calc R U . . .
C5 C 0.3584(5) 0.1351(4) 0.4616(2) 0.0158(7) Uani 1 1 d . . . . .
C10 C 0.4845(5) 0.4250(4) 0.7864(2) 0.0189(8) Uani 1 1 d . . . . .
C21 C 0.6335(5) 0.7071(4) 0.5277(2) 0.0152(7) Uani 1 1 d . . . . .
C22 C 0.3070(5) 0.5863(4) 0.4019(2) 0.0169(7) Uani 1 1 d . . . . .
H22 H 0.299436 0.495264 0.424639 0.020 Uiso 1 1 calc R U . . .
C31 C 0.8187(6) 0.3042(4) 0.0832(2) 0.0195(8) Uani 1 1 d . . . . .
C26 C 0.6004(6) 0.2433(4) 0.0941(2) 0.0180(7) Uani 1 1 d . . . . .
C6 C 0.6876(5) 0.2409(3) 0.5868(2) 0.0172(8) Uani 1 1 d . . . . .
H6 H 0.682144 0.133321 0.576408 0.021 Uiso 1 1 calc R U . . .
C25 C 0.5253(5) 0.4303(4) 0.1997(2) 0.0198(8) Uani 1 1 d . . . . .
C11 C 0.4113(6) 0.6194(4) 0.8848(2) 0.0193(8) Uani 1 1 d . . . . .
C30 C 0.4439(6) 0.1310(4) 0.0253(2) 0.0249(9) Uani 1 1 d . . . . .
C24 C 0.3969(5) 0.5668(4) 0.3192(2) 0.0169(7) Uani 1 1 d . . . . .
H24 H 0.412201 0.645160 0.290078 0.020 Uiso 1 1 calc R U . . .
C9 C 0.5147(5) 0.3828(3) 0.6959(2) 0.0172(7) Uani 1 1 d . . . . .
H9 H 0.452086 0.424272 0.652794 0.021 Uiso 1 1 calc R U . . .
C19 C 0.9492(6) 0.8633(3) 0.6547(2) 0.0176(8) Uani 1 1 d . . . . .
C14 C 0.3975(7) 0.7559(4) 1.0549(2) 0.0254(9) Uani 1 1 d . . . . .
C15 C 0.5966(6) 0.7931(4) 1.0254(2) 0.0244(8) Uani 1 1 d . . . . .
C13 C 0.2023(6) 0.6510(4) 0.9990(2) 0.0245(8) Uani 1 1 d . . . . .
C12 C 0.2109(6) 0.5834(4) 0.9144(2) 0.0228(8) Uani 1 1 d . . . . .
C32 C 0.4559(6) 0.4474(4) 0.2845(2) 0.0189(8) Uani 1 1 d . . . . .
H32 H 0.453500 0.371426 0.314901 0.023 Uiso 1 1 calc R U . . .
C28 C 0.8813(6) 0.2555(4) 0.0052(2) 0.0251(8) Uani 1 1 d . . . . .
C18 C 1.0338(6) 1.0347(3) 0.6918(2) 0.0239(8) Uani 1 1 d . . . . .
H18A H 1.080354 1.083750 0.646708 0.036 Uiso 1 1 calc R U . . .
H18B H 1.162089 1.060733 0.740816 0.036 Uiso 1 1 calc R U . . .
H18C H 0.912713 1.068453 0.711393 0.036 Uiso 1 1 calc R U . . .
C17 C 0.8522(6) 0.7819(4) 0.7208(2) 0.0260(9) Uani 1 1 d . . . . .
H17A H 0.721469 0.811519 0.733156 0.039 Uiso 1 1 calc R U . . .
H17B H 0.967135 0.809014 0.774455 0.039 Uiso 1 1 calc R U . . .
H17C H 0.806545 0.673419 0.696589 0.039 Uiso 1 1 calc R U . . .
C8 C 0.6301(5) 0.2861(4) 0.6749(2) 0.0203(8) Uani 1 1 d . . . . .
H8 H 0.680550 0.241865 0.718962 0.024 Uiso 1 1 calc R U . . .
C27 C 0.5061(7) 0.0838(4) -0.0529(2) 0.0298(9) Uani 1 1 d . . . . .
C16 C 0.6029(6) 0.7252(4) 0.9415(2) 0.0224(8) Uani 1 1 d . . . . .
C4 C 0.0264(5) 0.0627(3) 0.3376(2) 0.0185(8) Uani 1 1 d . . . . .
C20 C 1.1382(6) 0.8095(4) 0.6233(2) 0.0245(8) Uani 1 1 d . . . . .
H20A H 1.083181 0.700894 0.599173 0.037 Uiso 1 1 calc R U . . .
H20B H 1.266433 0.834165 0.672175 0.037 Uiso 1 1 calc R U . . .
H20C H 1.185431 0.859132 0.578516 0.037 Uiso 1 1 calc R U . . .
C1 C -0.1403(6) -0.0337(4) 0.3806(2) 0.0255(8) Uani 1 1 d . . . . .
H1A H -0.066098 -0.094340 0.409843 0.038 Uiso 1 1 calc R U . . .
H1B H -0.271354 -0.099567 0.336056 0.038 Uiso 1 1 calc R U . . .
H1C H -0.188959 0.031925 0.422990 0.038 Uiso 1 1 calc R U . . .
C29 C 0.7231(7) 0.1460(4) -0.0628(2) 0.0285(9) Uani 1 1 d . . . . .
C23 C 0.0658(6) 0.5993(4) 0.3817(2) 0.0228(8) Uani 1 1 d . . . . .
H23A H 0.004190 0.601167 0.433827 0.034 Uiso 1 1 calc R U . . .
H23B H -0.029913 0.513182 0.335283 0.034 Uiso 1 1 calc R U . . .
H23C H 0.071055 0.691774 0.363274 0.034 Uiso 1 1 calc R U . . .
C3 C -0.0923(6) 0.1589(4) 0.2922(2) 0.0287(9) Uani 1 1 d . . . . .
H3A H -0.145089 0.221460 0.334754 0.043 Uiso 1 1 calc R U . . .
H3B H -0.220625 0.093223 0.246476 0.043 Uiso 1 1 calc R U . . .
H3C H 0.013861 0.223029 0.266768 0.043 Uiso 1 1 calc R U . . .
C2 C 0.1259(6) -0.0298(4) 0.2738(2) 0.0278(9) Uani 1 1 d . . . . .
H2A H 0.223994 0.037115 0.247049 0.042 Uiso 1 1 calc R U . . .
H2B H 0.003685 -0.103592 0.228706 0.042 Uiso 1 1 calc R U . . .
H2C H 0.213258 -0.081533 0.305218 0.042 Uiso 1 1 calc R U . . .
C7 C 0.9322(6) 0.3357(4) 0.5897(2) 0.0223(8) Uani 1 1 d . . . . .
H7A H 0.980333 0.293672 0.538201 0.034 Uiso 1 1 calc R U . . .
H7B H 1.033388 0.333603 0.641833 0.034 Uiso 1 1 calc R U . . .
H7C H 0.936617 0.439253 0.590889 0.034 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
F10 C31 1.341(4) . ?
F4 C14 1.340(4) . ?
F3 C13 1.336(4) . ?
O1 C5 1.348(4) . ?
O1 C4 1.484(4) . ?
F2 C12 1.337(4) . ?
F1 C16 1.343(4) . ?
F9 C28 1.344(4) . ?
O5 C21 1.349(4) . ?
O5 C19 1.485(4) . ?
O6 C21 1.225(4) . ?
O4 C11 1.384(4) . ?
O4 C10 1.390(4) . ?
F5 C15 1.344(4) . ?
O8 C26 1.380(4) . ?
O8 C25 1.400(4) . ?
F7 C30 1.340(4) . ?
O2 C5 1.220(4) . ?
F6 C27 1.341(4) . ?
O7 C25 1.190(4) . ?
O3 C10 1.198(4) . ?
F8 C29 1.339(4) . ?
N2 C21 1.339(4) . ?
N2 C22 1.459(4) . ?
N2 H2 0.8600 . ?
N1 C5 1.344(4) . ?
N1 C6 1.455(4) . ?
N1 H1 0.8600 . ?
C10 C9 1.463(5) . ?
C22 C24 1.499(5) . ?
C22 C23 1.521(4) . ?
C22 H22 0.9800 . ?
C31 C26 1.373(5) . ?
C31 C28 1.381(5) . ?
C26 C30 1.383(5) . ?
C6 C8 1.502(5) . ?
C6 C7 1.529(5) . ?
C6 H6 0.9800 . ?
C25 C32 1.464(5) . ?
C11 C16 1.376(5) . ?
C11 C12 1.378(5) . ?
C30 C27 1.379(5) . ?
C24 C32 1.316(4) . ?
C24 H24 0.9300 . ?
C9 C8 1.321(4) . ?
C9 H9 0.9300 . ?
C19 C20 1.508(5) . ?
C19 C18 1.514(4) . ?
C19 C17 1.515(4) . ?
C14 C15 1.370(5) . ?
C14 C13 1.381(5) . ?
C15 C16 1.366(5) . ?
C13 C12 1.380(5) . ?
C32 H32 0.9300 . ?
C28 C29 1.371(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C8 H8 0.9300 . ?
C27 C29 1.363(5) . ?
C4 C2 1.514(5) . ?
C4 C3 1.518(4) . ?
C4 C1 1.518(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C4 119.8(2) . . ?
C21 O5 C19 121.3(2) . . ?
C11 O4 C10 115.7(2) . . ?
C26 O8 C25 117.1(2) . . ?
C21 N2 C22 121.8(3) . . ?
C21 N2 H2 119.1 . . ?
C22 N2 H2 119.1 . . ?
C5 N1 C6 121.3(3) . . ?
C5 N1 H1 119.3 . . ?
C6 N1 H1 119.3 . . ?
O2 C5 N1 124.5(3) . . ?
O2 C5 O1 124.8(3) . . ?
N1 C5 O1 110.7(3) . . ?
O3 C10 O4 121.5(3) . . ?
O3 C10 C9 128.5(3) . . ?
O4 C10 C9 110.0(3) . . ?
O6 C21 N2 124.4(3) . . ?
O6 C21 O5 124.9(3) . . ?
N2 C21 O5 110.6(3) . . ?
N2 C22 C24 110.5(3) . . ?
N2 C22 C23 111.4(3) . . ?
C24 C22 C23 110.3(3) . . ?
N2 C22 H22 108.2 . . ?
C24 C22 H22 108.2 . . ?
C23 C22 H22 108.2 . . ?
F10 C31 C26 119.9(3) . . ?
F10 C31 C28 119.1(3) . . ?
C26 C31 C28 121.0(3) . . ?
C31 C26 O8 121.8(3) . . ?
C31 C26 C30 118.7(3) . . ?
O8 C26 C30 119.4(3) . . ?
N1 C6 C8 113.1(3) . . ?
N1 C6 C7 110.3(3) . . ?
C8 C6 C7 109.3(3) . . ?
N1 C6 H6 108.0 . . ?
C8 C6 H6 108.0 . . ?
C7 C6 H6 108.0 . . ?
O7 C25 O8 122.3(3) . . ?
O7 C25 C32 129.2(3) . . ?
O8 C25 C32 108.5(3) . . ?
C16 C11 C12 118.4(3) . . ?
C16 C11 O4 120.5(3) . . ?
C12 C11 O4 121.1(3) . . ?
F7 C30 C27 119.9(3) . . ?
F7 C30 C26 119.9(3) . . ?
C27 C30 C26 120.3(3) . . ?
C32 C24 C22 125.0(3) . . ?
C32 C24 H24 117.5 . . ?
C22 C24 H24 117.5 . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
O5 C19 C20 110.5(3) . . ?
O5 C19 C18 101.8(2) . . ?
C20 C19 C18 109.8(3) . . ?
O5 C19 C17 109.9(3) . . ?
C20 C19 C17 113.0(3) . . ?
C18 C19 C17 111.3(3) . . ?
F4 C14 C15 120.5(3) . . ?
F4 C14 C13 119.8(3) . . ?
C15 C14 C13 119.6(3) . . ?
F5 C15 C16 120.5(3) . . ?
F5 C15 C14 119.3(3) . . ?
C16 C15 C14 120.2(3) . . ?
F3 C13 C12 120.3(3) . . ?
F3 C13 C14 120.2(3) . . ?
C12 C13 C14 119.6(3) . . ?
F2 C12 C11 119.6(3) . . ?
F2 C12 C13 119.4(3) . . ?
C11 C12 C13 121.0(3) . . ?
C24 C32 C25 122.1(3) . . ?
C24 C32 H32 119.0 . . ?
C25 C32 H32 119.0 . . ?
F9 C28 C29 120.7(3) . . ?
F9 C28 C31 119.7(3) . . ?
C29 C28 C31 119.7(3) . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 C17 H17A 109.5 . . ?
C19 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C19 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 C8 C6 126.2(3) . . ?
C9 C8 H8 116.9 . . ?
C6 C8 H8 116.9 . . ?
F6 C27 C29 119.7(3) . . ?
F6 C27 C30 119.9(4) . . ?
C29 C27 C30 120.4(3) . . ?
F1 C16 C15 119.2(3) . . ?
F1 C16 C11 119.5(3) . . ?
C15 C16 C11 121.2(3) . . ?
O1 C4 C2 109.2(3) . . ?
O1 C4 C3 102.8(2) . . ?
C2 C4 C3 110.9(3) . . ?
O1 C4 C1 110.7(3) . . ?
C2 C4 C1 113.7(3) . . ?
C3 C4 C1 109.0(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
F8 C29 C27 120.3(4) . . ?
F8 C29 C28 119.7(4) . . ?
C27 C29 C28 120.0(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_1f
_database_code_depnum_ccdc_archive 'CCDC 2212219'
loop_
_audit_author_name
_audit_author_address
'MANJEET SINGH'
;IISER PUNE
India
;
_audit_update_record             
;
2022-10-11 deposited with the CCDC.	2023-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C22
_chemical_formula_sum            'C22 H20 F5 N O4'
_chemical_formula_weight         457.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.469(6)
_cell_length_b                   9.455(6)
_cell_length_c                   11.567(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.556(14)
_cell_angle_gamma                90
_cell_volume                     1072.1(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1098
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      18.60

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             472.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.125
_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      120(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            15970
_diffrn_reflns_av_unetI/netI     0.1793
_diffrn_reflns_av_R_equivalents  0.1422
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.880
_diffrn_reflns_theta_max         28.448
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             4988
_reflns_number_gt                2439
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_max     0.843
_reflns_Friedel_fraction_full    0.894

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SAINT'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1000P)²] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.033(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 661 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.6(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4988
_refine_ls_number_parameters     293
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1674
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.2072
_refine_ls_wR_factor_gt          0.1476
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_restrained_S_all      0.893
_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 0.6671(4) 0.4613(4) 0.4750(4) 0.0199(10) Uani 1 1 d . . . . .
O2 O 0.5837(4) 0.2392(5) 0.4833(4) 0.0224(10) Uani 1 1 d . . . . .
F2 F -0.1235(5) 0.7569(5) 0.1844(4) 0.0468(13) Uani 1 1 d . . . . .
O3 O -0.0131(5) 0.4297(5) 0.2020(4) 0.0315(12) Uani 1 1 d . . . . .
F5 F -0.1652(6) 0.5929(6) -0.2770(4) 0.0584(15) Uani 1 1 d . . . . .
O4 O 0.0918(5) 0.6161(6) 0.1519(4) 0.0351(13) Uani 1 1 d . . . . .
N1 N 0.4773(5) 0.4392(6) 0.5151(5) 0.0213(12) Uani 1 1 d . . . . .
H1 H 0.483529 0.529382 0.524787 0.026 Uiso 1 1 calc R U . . .
F1 F 0.0620(5) 0.5307(6) -0.0826(5) 0.0563(14) Uani 1 1 d . . . . .
F4 F -0.3735(4) 0.7390(6) -0.2412(4) 0.0584(15) Uani 1 1 d . . . . .
F3 F -0.3502(5) 0.8210(6) -0.0113(5) 0.0631(16) Uani 1 1 d . . . . .
C5 C 0.5769(6) 0.3682(7) 0.4913(6) 0.0218(15) Uani 1 1 d . . . . .
C6 C 0.3597(6) 0.3658(7) 0.5245(6) 0.0198(14) Uani 1 1 d . . . . .
H6 H 0.377776 0.263963 0.526445 0.024 Uiso 1 1 calc R U . . .
C16 C 0.0865(7) 0.4997(7) 0.2236(6) 0.0254(16) Uani 1 1 d . . . . .
C15 C 0.2177(7) 0.4860(7) 0.3254(6) 0.0269(16) Uani 1 1 d . . . . .
H15 H 0.291330 0.541446 0.326073 0.032 Uiso 1 1 calc R U . . .
C8 C 0.4524(7) 0.3584(8) 0.7602(6) 0.0243(15) Uani 1 1 d . . . . .
C17 C -0.0265(7) 0.6440(8) 0.0542(6) 0.0265(16) Uani 1 1 d . . . . .
C14 C 0.2320(6) 0.3952(7) 0.4164(6) 0.0207(14) Uani 1 1 d . . . . .
H14 H 0.154696 0.344341 0.412989 0.025 Uiso 1 1 calc R U . . .
C3 C 0.7837(7) 0.4116(7) 0.4406(6) 0.0246(15) Uani 1 1 d . . . . .
C18 C -0.1322(7) 0.7171(8) 0.0703(6) 0.0282(16) Uani 1 1 d . . . . .
C7 C 0.3369(7) 0.4058(7) 0.6454(6) 0.0234(15) Uani 1 1 d . . . . .
H7A H 0.327045 0.507591 0.648235 0.028 Uiso 1 1 calc R U . . .
H7B H 0.252573 0.363103 0.645184 0.028 Uiso 1 1 calc R U . . .
C19 C -0.2482(7) 0.7493(8) -0.0288(7) 0.0319(17) Uani 1 1 d . . . . .
C4 C 0.8584(7) 0.5454(8) 0.4364(7) 0.0319(17) Uani 1 1 d . . . . .
H4A H 0.797847 0.609701 0.378542 0.048 Uiso 1 1 calc R U . . .
H4B H 0.934355 0.524355 0.411060 0.048 Uiso 1 1 calc R U . . .
H4C H 0.890889 0.587881 0.516893 0.048 Uiso 1 1 calc R U . . .
C1 C 0.8739(7) 0.3129(8) 0.5391(7) 0.0330(17) Uani 1 1 d . . . . .
H1A H 0.890000 0.352946 0.619239 0.050 Uiso 1 1 calc R U . . .
H1B H 0.959385 0.300256 0.527027 0.050 Uiso 1 1 calc R U . . .
H1C H 0.829507 0.222960 0.533305 0.050 Uiso 1 1 calc R U . . .
C22 C -0.0397(8) 0.6017(8) -0.0642(7) 0.0305(17) Uani 1 1 d . . . . .
C12 C 0.5009(7) 0.2204(8) 0.7759(7) 0.0329(18) Uani 1 1 d . . . . .
H12 H 0.463470 0.154861 0.713080 0.039 Uiso 1 1 calc R U . . .
C20 C -0.2593(7) 0.7084(9) -0.1452(7) 0.0369(19) Uani 1 1 d . . . . .
C21 C -0.1551(8) 0.6355(8) -0.1636(6) 0.0341(19) Uani 1 1 d . . . . .
C2 C 0.7284(8) 0.3436(8) 0.3138(6) 0.0362(19) Uani 1 1 d . . . . .
H2A H 0.682715 0.256997 0.318679 0.054 Uiso 1 1 calc R U . . .
H2B H 0.802365 0.323963 0.285359 0.054 Uiso 1 1 calc R U . . .
H2C H 0.665091 0.406907 0.257142 0.054 Uiso 1 1 calc R U . . .
C11 C 0.6035(8) 0.1785(9) 0.8828(7) 0.039(2) Uani 1 1 d . . . . .
H11 H 0.632972 0.084984 0.891749 0.047 Uiso 1 1 calc R U . . .
C9 C 0.5129(8) 0.4534(9) 0.8560(7) 0.0348(18) Uani 1 1 d . . . . .
H9 H 0.482801 0.546707 0.847971 0.042 Uiso 1 1 calc R U . . .
C10 C 0.6626(7) 0.2739(9) 0.9761(7) 0.039(2) Uani 1 1 d . . . . .
H10 H 0.732755 0.245438 1.047303 0.047 Uiso 1 1 calc R U . . .
C13 C 0.6173(8) 0.4119(10) 0.9636(7) 0.043(2) Uani 1 1 d . . . . .
H13 H 0.656097 0.476822 1.026539 0.052 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 C5 1.353(7) . ?
O1 C3 1.486(7) . ?
O2 C5 1.227(8) . ?
F2 C18 1.344(8) . ?
O3 C16 1.185(8) . ?
F5 C21 1.340(8) . ?
O4 C17 1.378(8) . ?
O4 C16 1.391(8) . ?
N1 C5 1.347(8) . ?
N1 C6 1.450(8) . ?
N1 H1 0.8600 . ?
F1 C22 1.338(8) . ?
F4 C20 1.347(8) . ?
F3 C19 1.339(8) . ?
C6 C14 1.501(9) . ?
C6 C7 1.546(9) . ?
C6 H6 0.9800 . ?
C16 C15 1.468(9) . ?
C15 C14 1.326(9) . ?
C15 H15 0.9300 . ?
C8 C12 1.389(10) . ?
C8 C9 1.394(10) . ?
C8 C7 1.516(9) . ?
C17 C18 1.371(10) . ?
C17 C22 1.386(10) . ?
C14 H14 0.9300 . ?
C3 C4 1.497(10) . ?
C3 C2 1.518(9) . ?
C3 C1 1.519(9) . ?
C18 C19 1.381(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C19 C20 1.366(11) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C22 C21 1.381(11) . ?
C12 C11 1.381(10) . ?
C12 H12 0.9300 . ?
C20 C21 1.369(11) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C11 C10 1.376(11) . ?
C11 H11 0.9300 . ?
C9 C13 1.394(10) . ?
C9 H9 0.9300 . ?
C10 C13 1.378(12) . ?
C10 H10 0.9300 . ?
C13 H13 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
C5 O1 C3 120.8(5) . . ?
C17 O4 C16 115.3(5) . . ?
C5 N1 C6 121.0(6) . . ?
C5 N1 H1 119.5 . . ?
C6 N1 H1 119.5 . . ?
O2 C5 N1 125.5(6) . . ?
O2 C5 O1 125.0(6) . . ?
N1 C5 O1 109.5(6) . . ?
N1 C6 C14 112.3(5) . . ?
N1 C6 C7 110.8(5) . . ?
C14 C6 C7 109.4(5) . . ?
N1 C6 H6 108.0 . . ?
C14 C6 H6 108.0 . . ?
C7 C6 H6 108.0 . . ?
O3 C16 O4 122.2(6) . . ?
O3 C16 C15 128.8(6) . . ?
O4 C16 C15 109.0(6) . . ?
C14 C15 C16 120.5(6) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C12 C8 C9 117.3(7) . . ?
C12 C8 C7 122.3(6) . . ?
C9 C8 C7 120.4(7) . . ?
C18 C17 O4 121.4(6) . . ?
C18 C17 C22 118.3(6) . . ?
O4 C17 C22 120.3(7) . . ?
C15 C14 C6 126.9(6) . . ?
C15 C14 H14 116.6 . . ?
C6 C14 H14 116.6 . . ?
O1 C3 C4 103.3(5) . . ?
O1 C3 C2 108.8(5) . . ?
C4 C3 C2 110.7(6) . . ?
O1 C3 C1 110.3(5) . . ?
C4 C3 C1 110.4(6) . . ?
C2 C3 C1 113.0(6) . . ?
F2 C18 C17 119.7(6) . . ?
F2 C18 C19 119.4(7) . . ?
C17 C18 C19 121.0(6) . . ?
C8 C7 C6 113.0(5) . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
F3 C19 C20 119.8(7) . . ?
F3 C19 C18 120.1(7) . . ?
C20 C19 C18 120.1(7) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
F1 C22 C21 119.7(6) . . ?
F1 C22 C17 119.6(7) . . ?
C21 C22 C17 120.7(7) . . ?
C11 C12 C8 121.3(7) . . ?
C11 C12 H12 119.3 . . ?
C8 C12 H12 119.3 . . ?
F4 C20 C19 119.7(7) . . ?
F4 C20 C21 120.3(7) . . ?
C19 C20 C21 120.0(7) . . ?
F5 C21 C20 120.7(7) . . ?
F5 C21 C22 119.4(7) . . ?
C20 C21 C22 119.9(7) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C10 C11 C12 120.6(8) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C8 C9 C13 121.5(8) . . ?
C8 C9 H9 119.2 . . ?
C13 C9 H9 119.2 . . ?
C11 C10 C13 119.6(8) . . ?
C11 C10 H10 120.2 . . ?
C13 C10 H10 120.2 . . ?
C10 C13 C9 119.6(8) . . ?
C10 C13 H13 120.2 . . ?
C9 C13 H13 120.2 . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_1k
_database_code_depnum_ccdc_archive 'CCDC 2212220'
loop_
_audit_author_name
_audit_author_address
'MANJEET SINGH'
;IISER PUNE
India
;
_audit_update_record             
;
2022-10-11 deposited with the CCDC.	2023-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C18
_chemical_formula_sum            'C18 H24 N2 O6'
_chemical_formula_weight         364.39

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.216(3)
_cell_length_b                   5.362(3)
_cell_length_c                   28.415(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.424(12)
_cell_angle_gamma                90
_cell_volume                     942.8(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6777
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      26.03

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.097
_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            26912
_diffrn_reflns_av_unetI/netI     0.1554
_diffrn_reflns_av_R_equivalents  0.1842
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.160
_diffrn_reflns_theta_max         28.801
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4704
_reflns_number_gt                3029
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_max     0.944
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1145P)²+0.0648P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.090(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 935 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4704
_refine_ls_number_parameters     241
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1436
_refine_ls_R_factor_gt           0.0899
_refine_ls_wR_factor_ref         0.2324
_refine_ls_wR_factor_gt          0.2110
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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
O3 O 0.2505(7) 0.3078(8) 0.32591(14) 0.0257(10) Uani 1 1 d . . . . .
O4 O 0.4616(7) 0.5879(7) 0.36715(13) 0.0235(10) Uani 1 1 d . . . . .
O5 O 1.0878(7) -0.2645(8) 0.44259(14) 0.0288(11) Uani 1 1 d . . . . .
O6 O 0.8324(7) -0.3204(8) 0.48863(14) 0.0265(10) Uani 1 1 d . . . . .
O1 O 0.2459(7) 0.9825(8) 0.11546(13) 0.0274(10) Uani 1 1 d . . . . .
O2 O 0.1499(7) 1.2880(8) 0.16595(14) 0.0286(10) Uani 1 1 d . . . . .
N2 N 0.9137(8) -0.2090(9) 0.45724(16) 0.0213(11) Uani 1 1 d . . . . .
N1 N 0.1283(8) 0.8749(9) 0.18377(15) 0.0209(11) Uani 1 1 d . . . . .
H1 H 0.150377 0.725236 0.174439 0.025 Uiso 1 1 calc R U . . .
C14 C 0.7973(9) 0.0084(11) 0.43501(18) 0.0173(12) Uani 1 1 d . . . . .
C10 C 0.1246(9) 0.7066(10) 0.26223(18) 0.0178(12) Uani 1 1 d . . . . .
H10 H 0.103635 0.543790 0.251463 0.021 Uiso 1 1 calc R U . . .
C11 C 0.2223(9) 0.7378(10) 0.30495(18) 0.0179(12) Uani 1 1 d . . . . .
H11 H 0.237777 0.897169 0.317740 0.021 Uiso 1 1 calc R U . . .
C18 C 0.8895(10) 0.1363(11) 0.39991(18) 0.0220(13) Uani 1 1 d . . . . .
H18 H 1.025029 0.092409 0.391226 0.026 Uiso 1 1 calc R U . . .
C13 C 0.5740(10) 0.3875(10) 0.39111(18) 0.0199(12) Uani 1 1 d . . . . .
C16 C 0.4816(9) 0.2643(11) 0.42680(19) 0.0202(12) Uani 1 1 d . . . . .
H16 H 0.347146 0.311080 0.435672 0.024 Uiso 1 1 calc R U . . .
C6 C 0.0447(9) 0.9124(11) 0.22963(18) 0.0186(12) Uani 1 1 d . . . . .
H6 H 0.103272 1.069837 0.242830 0.022 Uiso 1 1 calc R U . . .
C15 C 0.5967(9) 0.0673(11) 0.44910(19) 0.0209(13) Uani 1 1 d . . . . .
H15 H 0.539636 -0.022727 0.472991 0.025 Uiso 1 1 calc R U . . .
C7 C -0.2031(9) 0.9335(11) 0.22396(19) 0.0215(13) Uani 1 1 d . . . . .
H7 H -0.241327 1.059379 0.199603 0.026 Uiso 1 1 calc R U . . .
C12 C 0.3075(9) 0.5204(11) 0.33262(18) 0.0186(12) Uani 1 1 d . . . . .
C3 C 0.3119(10) 1.1562(12) 0.07953(19) 0.0257(14) Uani 1 1 d . . . . .
C17 C 0.7745(10) 0.3319(11) 0.37798(19) 0.0219(13) Uani 1 1 d . . . . .
H17 H 0.832817 0.424409 0.354590 0.026 Uiso 1 1 calc R U . . .
C2 C 0.3864(13) 0.9779(13) 0.0424(2) 0.0376(17) Uani 1 1 d . . . . .
H2A H 0.511245 0.887559 0.055546 0.056 Uiso 1 1 calc R U . . .
H2B H 0.422521 1.071497 0.015425 0.056 Uiso 1 1 calc R U . . .
H2C H 0.272342 0.862698 0.032861 0.056 Uiso 1 1 calc R U . . .
C5 C 0.1717(10) 1.0665(11) 0.1557(2) 0.0219(13) Uani 1 1 d . . . . .
C8 C -0.2896(12) 1.0238(13) 0.2695(2) 0.0333(16) Uani 1 1 d . . . . .
H8A H -0.442083 1.054109 0.263792 0.050 Uiso 1 1 calc R U . . .
H8B H -0.217415 1.175309 0.279701 0.050 Uiso 1 1 calc R U . . .
H8C H -0.263861 0.898746 0.293515 0.050 Uiso 1 1 calc R U . . .
C1 C 0.4981(11) 1.3171(13) 0.0996(2) 0.0319(15) Uani 1 1 d . . . . .
H1A H 0.448280 1.431826 0.122108 0.048 Uiso 1 1 calc R U . . .
H1B H 0.554916 1.408416 0.074464 0.048 Uiso 1 1 calc R U . . .
H1C H 0.609401 1.213202 0.114912 0.048 Uiso 1 1 calc R U . . .
C9 C -0.3118(11) 0.6883(14) 0.2070(3) 0.0387(17) Uani 1 1 d . . . . .
H9A H -0.304617 0.571419 0.232736 0.058 Uiso 1 1 calc R U . . .
H9B H -0.238537 0.620565 0.181656 0.058 Uiso 1 1 calc R U . . .
H9C H -0.460269 0.719490 0.196139 0.058 Uiso 1 1 calc R U . . .
C4 C 0.1176(12) 1.3050(14) 0.0590(2) 0.0361(17) Uani 1 1 d . . . . .
H4A H 0.000344 1.193375 0.049742 0.054 Uiso 1 1 calc R U . . .
H4B H 0.154874 1.396234 0.031816 0.054 Uiso 1 1 calc R U . . .
H4C H 0.074569 1.419486 0.082296 0.054 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
O3 C12 1.203(7) . ?
O4 C12 1.354(7) . ?
O4 C13 1.420(7) . ?
O5 N2 1.232(6) . ?
O6 N2 1.222(6) . ?
O1 C5 1.350(7) . ?
O1 C3 1.469(7) . ?
O2 C5 1.233(7) . ?
N2 C14 1.481(7) . ?
N1 C5 1.343(7) . ?
N1 C6 1.462(7) . ?
N1 H1 0.8600 . ?
C14 C18 1.379(8) . ?
C14 C15 1.382(8) . ?
C10 C11 1.316(7) . ?
C10 C6 1.495(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.476(8) . ?
C11 H11 0.9300 . ?
C18 C17 1.384(8) . ?
C18 H18 0.9300 . ?
C13 C17 1.367(8) . ?
C13 C16 1.380(8) . ?
C16 C15 1.394(8) . ?
C16 H16 0.9300 . ?
C6 C7 1.537(8) . ?
C6 H6 0.9800 . ?
C15 H15 0.9300 . ?
C7 C8 1.525(8) . ?
C7 C9 1.534(9) . ?
C7 H7 0.9800 . ?
C3 C1 1.511(9) . ?
C3 C4 1.518(9) . ?
C3 C2 1.528(9) . ?
C17 H17 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

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
C12 O4 C13 115.3(4) . . ?
C5 O1 C3 121.2(5) . . ?
O6 N2 O5 124.4(5) . . ?
O6 N2 C14 118.5(5) . . ?
O5 N2 C14 117.1(5) . . ?
C5 N1 C6 122.2(5) . . ?
C5 N1 H1 118.9 . . ?
C6 N1 H1 118.9 . . ?
C18 C14 C15 123.0(5) . . ?
C18 C14 N2 118.7(5) . . ?
C15 C14 N2 118.3(5) . . ?
C11 C10 C6 125.1(5) . . ?
C11 C10 H10 117.4 . . ?
C6 C10 H10 117.4 . . ?
C10 C11 C12 120.1(5) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C14 C18 C17 118.0(6) . . ?
C14 C18 H18 121.0 . . ?
C17 C18 H18 121.0 . . ?
C17 C13 C16 123.3(5) . . ?
C17 C13 O4 117.0(5) . . ?
C16 C13 O4 119.6(5) . . ?
C13 C16 C15 117.7(5) . . ?
C13 C16 H16 121.1 . . ?
C15 C16 H16 121.1 . . ?
N1 C6 C10 109.0(4) . . ?
N1 C6 C7 110.7(4) . . ?
C10 C6 C7 113.0(5) . . ?
N1 C6 H6 108.0 . . ?
C10 C6 H6 108.0 . . ?
C7 C6 H6 108.0 . . ?
C14 C15 C16 118.7(5) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C8 C7 C9 110.9(6) . . ?
C8 C7 C6 111.4(5) . . ?
C9 C7 C6 112.1(5) . . ?
C8 C7 H7 107.4 . . ?
C9 C7 H7 107.4 . . ?
C6 C7 H7 107.4 . . ?
O3 C12 O4 123.0(5) . . ?
O3 C12 C11 125.3(5) . . ?
O4 C12 C11 111.6(5) . . ?
O1 C3 C1 110.7(5) . . ?
O1 C3 C4 109.7(5) . . ?
C1 C3 C4 113.5(6) . . ?
O1 C3 C2 101.9(5) . . ?
C1 C3 C2 110.3(6) . . ?
C4 C3 C2 110.2(5) . . ?
C13 C17 C18 119.2(5) . . ?
C13 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O2 C5 N1 124.3(5) . . ?
O2 C5 O1 125.1(5) . . ?
N1 C5 O1 110.6(5) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

_refine_diff_density_max         0.544
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.102

####################################################################### 
# 
# 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_2g
_database_code_depnum_ccdc_archive 'CCDC 2212223'
loop_
_audit_author_name
_audit_author_address
'MANJEET SINGH'
;IISER PUNE
India
;
_audit_update_record             
;
2022-10-11 deposited with the CCDC.	2023-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C15
_chemical_formula_sum            'C15 H17 N O3'
_chemical_formula_weight         259.30

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.2063(11)
_cell_length_b                   13.323(3)
_cell_length_c                   16.945(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.668(6)
_cell_angle_gamma                90
_cell_volume                     1400.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3346
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      22.91

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.086
_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            20800
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.945
_diffrn_reflns_theta_max         28.380
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3509
_reflns_number_gt                2549
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0400P)²+0.3889P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0053(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3509
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.32765(13) 0.61103(7) 0.31144(5) 0.0220(2) Uani 1 1 d . . . . .
O2 O -0.02826(14) 0.61718(8) 0.27603(5) 0.0263(2) Uani 1 1 d . . . . .
O3 O -0.08508(15) 0.55593(8) 0.11638(6) 0.0325(3) Uani 1 1 d . . . . .
N1 N 0.22195(16) 0.54110(8) 0.19857(6) 0.0196(2) Uani 1 1 d . . . . .
C5 C 0.1550(2) 0.59358(10) 0.26479(7) 0.0191(3) Uani 1 1 d . . . . .
C10 C 0.4829(2) 0.41375(10) 0.25204(7) 0.0197(3) Uani 1 1 d . . . . .
C2 C 0.3038(2) 0.64367(11) 0.39430(7) 0.0239(3) Uani 1 1 d . . . . .
C6 C 0.0992(2) 0.52822(10) 0.12857(8) 0.0226(3) Uani 1 1 d . . . . .
C9 C 0.4389(2) 0.49773(10) 0.19260(7) 0.0206(3) Uani 1 1 d . . . . .
H9 H 0.547971 0.550474 0.199171 0.025 Uiso 1 1 calc R U . . .
C15 C 0.3271(2) 0.34194(10) 0.26761(8) 0.0246(3) Uani 1 1 d . . . . .
H15 H 0.193472 0.344922 0.241406 0.030 Uiso 1 1 calc R U . . .
C8 C 0.4325(2) 0.46085(10) 0.10888(8) 0.0248(3) Uani 1 1 d . . . . .
H8 H 0.548420 0.430646 0.084669 0.030 Uiso 1 1 calc R U . . .
C7 C 0.2425(2) 0.47640(11) 0.07361(8) 0.0261(3) Uani 1 1 d . . . . .
H7 H 0.204889 0.457626 0.022174 0.031 Uiso 1 1 calc R U . . .
C13 C 0.5691(2) 0.26020(11) 0.35999(8) 0.0287(3) Uani 1 1 d . . . . .
H13 H 0.597617 0.209517 0.396567 0.034 Uiso 1 1 calc R U . . .
C11 C 0.6833(2) 0.40716(11) 0.29023(8) 0.0251(3) Uani 1 1 d . . . . .
H11 H 0.789072 0.454502 0.280115 0.030 Uiso 1 1 calc R U . . .
C14 C 0.3690(2) 0.26595(11) 0.32180(8) 0.0280(3) Uani 1 1 d . . . . .
H14 H 0.263042 0.218930 0.332512 0.034 Uiso 1 1 calc R U . . .
C12 C 0.7261(2) 0.33001(11) 0.34353(8) 0.0293(3) Uani 1 1 d . . . . .
H12 H 0.861457 0.325322 0.368304 0.035 Uiso 1 1 calc R U . . .
C1 C 0.1784(2) 0.74135(12) 0.39840(9) 0.0321(3) Uani 1 1 d . . . . .
H1A H 0.231648 0.787685 0.360204 0.048 Uiso 1 1 calc R U . . .
H1B H 0.195996 0.769619 0.450304 0.048 Uiso 1 1 calc R U . . .
H1C H 0.028391 0.728496 0.387294 0.048 Uiso 1 1 calc R U . . .
C3 C 0.5367(2) 0.65849(13) 0.42092(9) 0.0357(4) Uani 1 1 d . . . . .
H3A H 0.615087 0.597252 0.413535 0.054 Uiso 1 1 calc R U . . .
H3B H 0.543085 0.676626 0.475770 0.054 Uiso 1 1 calc R U . . .
H3C H 0.599525 0.710984 0.390337 0.054 Uiso 1 1 calc R U . . .
C4 C 0.1980(3) 0.55886(13) 0.43857(9) 0.0390(4) Uani 1 1 d . . . . .
H4A H 0.053608 0.549258 0.418067 0.059 Uiso 1 1 calc R U . . .
H4B H 0.194165 0.575383 0.493653 0.059 Uiso 1 1 calc R U . . .
H4C H 0.279133 0.498242 0.432007 0.059 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 C5 1.3333(15) . ?
O1 C2 1.4815(15) . ?
O2 C5 1.2007(15) . ?
O3 C6 1.2138(16) . ?
N1 C5 1.3957(16) . ?
N1 C6 1.4014(17) . ?
N1 C9 1.4712(16) . ?
C10 C11 1.3881(18) . ?
C10 C15 1.3910(18) . ?
C10 C9 1.5247(18) . ?
C2 C3 1.5146(19) . ?
C2 C4 1.516(2) . ?
C2 C1 1.519(2) . ?
C6 C7 1.4774(19) . ?
C9 C8 1.5008(18) . ?
C9 H9 0.9800 . ?
C15 C14 1.386(2) . ?
C15 H15 0.9300 . ?
C8 C7 1.3229(19) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?
C13 C12 1.381(2) . ?
C13 C14 1.386(2) . ?
C13 H13 0.9300 . ?
C11 C12 1.389(2) . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C12 H12 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C2 120.82(10) . . ?
C5 N1 C6 125.08(11) . . ?
C5 N1 C9 123.12(10) . . ?
C6 N1 C9 111.70(10) . . ?
O2 C5 O1 127.51(12) . . ?
O2 C5 N1 124.36(12) . . ?
O1 C5 N1 108.13(10) . . ?
C11 C10 C15 119.11(12) . . ?
C11 C10 C9 119.69(12) . . ?
C15 C10 C9 121.19(11) . . ?
O1 C2 C3 101.51(10) . . ?
O1 C2 C4 107.86(11) . . ?
C3 C2 C4 111.91(13) . . ?
O1 C2 C1 111.13(11) . . ?
C3 C2 C1 111.12(12) . . ?
C4 C2 C1 112.71(13) . . ?
O3 C6 N1 126.38(12) . . ?
O3 C6 C7 128.04(12) . . ?
N1 C6 C7 105.57(11) . . ?
N1 C9 C8 101.22(10) . . ?
N1 C9 C10 112.93(10) . . ?
C8 C9 C10 112.55(11) . . ?
N1 C9 H9 109.9 . . ?
C8 C9 H9 109.9 . . ?
C10 C9 H9 109.9 . . ?
C14 C15 C10 120.65(13) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C7 C8 C9 111.98(12) . . ?
C7 C8 H8 124.0 . . ?
C9 C8 H8 124.0 . . ?
C8 C7 C6 109.48(12) . . ?
C8 C7 H7 125.3 . . ?
C6 C7 H7 125.3 . . ?
C12 C13 C14 119.76(13) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C10 C11 C12 120.14(13) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C14 C15 119.88(13) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C13 C12 C11 120.44(13) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_1l
_database_code_depnum_ccdc_archive 'CCDC 2212221'
loop_
_audit_author_name
_audit_author_address
'MANJEET SINGH'
;IISER PUNE
India
;
_audit_update_record             
;
2022-10-11 deposited with the CCDC.	2023-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C22
_chemical_formula_sum            'C22 H24 N2 O6'
_chemical_formula_weight         412.43

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.1910(7)
_cell_length_b                   14.7184(16)
_cell_length_c                   22.774(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2075.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9863
_cell_measurement_theta_min      3.58
_cell_measurement_theta_max      66.72

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.803
_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     1.54178
_diffrn_radiation_type           CuK\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            69965
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_av_R_equivalents  0.1486
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.575
_diffrn_reflns_theta_max         66.768
_diffrn_reflns_theta_full        66.768
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3681
_reflns_number_gt                3070
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.716
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0586P)²+0.0524P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1126 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.25(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3681
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.0993
_refine_ls_wR_factor_gt          0.0922
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
O4 O 0.5421(3) 0.47776(13) 0.43082(9) 0.0268(5) Uani 1 1 d . . . . .
O3 O 0.3162(3) 0.57618(14) 0.47644(8) 0.0268(5) Uani 1 1 d . . . . .
O1 O 1.2098(4) 0.43575(13) 0.58116(9) 0.0303(5) Uani 1 1 d . . . . .
O2 O 0.9482(4) 0.45721(14) 0.65052(10) 0.0336(5) Uani 1 1 d . . . . .
O5 O -0.1682(4) 0.36315(17) 0.25037(11) 0.0451(7) Uani 1 1 d . . . . .
N1 N 1.0446(4) 0.56761(16) 0.58574(10) 0.0234(5) Uani 1 1 d . . . . .
H1 H 1.146726 0.586495 0.563252 0.028 Uiso 1 1 calc R U . . .
O6 O 0.0753(4) 0.41463(18) 0.19129(10) 0.0466(7) Uani 1 1 d . . . . .
N2 N 0.0076(4) 0.39826(18) 0.24050(13) 0.0316(7) Uani 1 1 d . . . . .
C16 C 0.3957(5) 0.46261(19) 0.38469(13) 0.0236(7) Uani 1 1 d . . . . .
C8 C 1.0904(5) 0.76548(19) 0.62562(13) 0.0230(7) Uani 1 1 d . . . . .
C22 C 0.4878(5) 0.5380(2) 0.47444(13) 0.0235(7) Uani 1 1 d . . . . .
C5 C 1.0577(5) 0.48377(19) 0.60994(13) 0.0236(7) Uani 1 1 d . . . . .
C17 C 0.1938(5) 0.4271(2) 0.39479(13) 0.0270(7) Uani 1 1 d . . . . .
H17 H 0.144911 0.417159 0.432871 0.032 Uiso 1 1 calc R U . . .
C15 C 0.6726(5) 0.54868(19) 0.51401(13) 0.0250(7) Uani 1 1 d . . . . .
H15 H 0.797749 0.515750 0.506384 0.030 Uiso 1 1 calc R U . . .
C21 C 0.1440(5) 0.4217(2) 0.29104(13) 0.0247(7) Uani 1 1 d . . . . .
C9 C 1.2790(5) 0.80228(19) 0.60366(14) 0.0277(7) Uani 1 1 d . . . . .
H9 H 1.306359 0.799002 0.563564 0.033 Uiso 1 1 calc R U . . .
C20 C 0.0648(5) 0.40631(19) 0.34697(13) 0.0279(7) Uani 1 1 d . . . . .
H20 H -0.072848 0.382412 0.352364 0.033 Uiso 1 1 calc R U . . .
C6 C 0.8614(5) 0.62579(19) 0.59714(13) 0.0222(7) Uani 1 1 d . . . . .
H6 H 0.820955 0.619879 0.638567 0.027 Uiso 1 1 calc R U . . .
C14 C 0.6689(5) 0.60300(19) 0.55991(13) 0.0244(7) Uani 1 1 d . . . . .
H14 H 0.537274 0.629156 0.570013 0.029 Uiso 1 1 calc R U . . .
C18 C 0.4727(5) 0.4793(2) 0.32869(13) 0.0283(7) Uani 1 1 d . . . . .
H18 H 0.609020 0.504430 0.323296 0.034 Uiso 1 1 calc R U . . .
C7 C 0.9239(5) 0.72555(19) 0.58501(13) 0.0270(7) Uani 1 1 d . . . . .
H7A H 0.977878 0.729764 0.545112 0.032 Uiso 1 1 calc R U . . .
H7B H 0.794301 0.762404 0.587301 0.032 Uiso 1 1 calc R U . . .
C13 C 1.0529(6) 0.7708(2) 0.68590(13) 0.0306(7) Uani 1 1 d . . . . .
H13 H 0.926199 0.747082 0.701610 0.037 Uiso 1 1 calc R U . . .
C10 C 1.4283(5) 0.8440(2) 0.64007(15) 0.0325(8) Uani 1 1 d . . . . .
H10 H 1.553496 0.869267 0.624494 0.039 Uiso 1 1 calc R U . . .
C19 C 0.3454(5) 0.4582(2) 0.28102(13) 0.0281(7) Uani 1 1 d . . . . .
H19 H 0.394302 0.468366 0.242971 0.034 Uiso 1 1 calc R U . . .
C12 C 1.2041(6) 0.8112(2) 0.72253(15) 0.0369(8) Uani 1 1 d . . . . .
H12 H 1.179543 0.813617 0.762785 0.044 Uiso 1 1 calc R U . . .
C2 C 1.2723(6) 0.3445(2) 0.60210(14) 0.0306(8) Uani 1 1 d . . . . .
C11 C 1.3896(6) 0.8476(2) 0.69954(15) 0.0360(8) Uani 1 1 d . . . . .
H11 H 1.489893 0.874927 0.724286 0.043 Uiso 1 1 calc R U . . .
C3 C 1.3659(6) 0.3514(2) 0.66314(15) 0.0401(9) Uani 1 1 d . . . . .
H3A H 1.481235 0.394947 0.663300 0.060 Uiso 1 1 calc R U . . .
H3B H 1.420553 0.293115 0.674920 0.060 Uiso 1 1 calc R U . . .
H3C H 1.255317 0.370366 0.690025 0.060 Uiso 1 1 calc R U . . .
C4 C 1.0804(7) 0.2809(2) 0.59865(17) 0.0465(10) Uani 1 1 d . . . . .
H4A H 0.978539 0.296111 0.628864 0.070 Uiso 1 1 calc R U . . .
H4B H 1.128442 0.219398 0.603969 0.070 Uiso 1 1 calc R U . . .
H4C H 1.012627 0.286743 0.560924 0.070 Uiso 1 1 calc R U . . .
C1 C 1.4440(7) 0.3185(2) 0.55839(18) 0.0531(11) Uani 1 1 d . . . . .
H1A H 1.385688 0.321703 0.519393 0.080 Uiso 1 1 calc R U . . .
H1B H 1.491807 0.257589 0.566182 0.080 Uiso 1 1 calc R U . . .
H1C H 1.564004 0.359448 0.561743 0.080 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
O4 C22 1.373(3) . ?
O4 C16 1.406(4) . ?
O3 C22 1.203(4) . ?
O1 C5 1.348(3) . ?
O1 C2 1.476(3) . ?
O2 C5 1.211(4) . ?
O5 N2 1.226(3) . ?
N1 C5 1.354(4) . ?
N1 C6 1.444(4) . ?
N1 H1 0.8600 . ?
O6 N2 1.220(4) . ?
N2 C21 1.469(4) . ?
C16 C17 1.374(4) . ?
C16 C18 1.383(4) . ?
C8 C9 1.381(4) . ?
C8 C13 1.394(4) . ?
C8 C7 1.504(4) . ?
C22 C15 1.465(4) . ?
C17 C20 1.384(4) . ?
C17 H17 0.9300 . ?
C15 C14 1.316(4) . ?
C15 H15 0.9300 . ?
C21 C19 1.377(4) . ?
C21 C20 1.384(4) . ?
C9 C10 1.385(5) . ?
C9 H9 0.9300 . ?
C20 H20 0.9300 . ?
C6 C14 1.501(4) . ?
C6 C7 1.543(4) . ?
C6 H6 0.9800 . ?
C14 H14 0.9300 . ?
C18 C19 1.377(4) . ?
C18 H18 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C13 C12 1.388(4) . ?
C13 H13 0.9300 . ?
C10 C11 1.376(5) . ?
C10 H10 0.9300 . ?
C19 H19 0.9300 . ?
C12 C11 1.371(5) . ?
C12 H12 0.9300 . ?
C2 C1 1.506(5) . ?
C2 C3 1.509(5) . ?
C2 C4 1.516(5) . ?
C11 H11 0.9300 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 O4 C16 119.0(2) . . ?
C5 O1 C2 120.2(2) . . ?
C5 N1 C6 120.9(3) . . ?
C5 N1 H1 119.5 . . ?
C6 N1 H1 119.5 . . ?
O6 N2 O5 123.8(3) . . ?
O6 N2 C21 118.4(3) . . ?
O5 N2 C21 117.8(3) . . ?
C17 C16 C18 122.4(3) . . ?
C17 C16 O4 121.5(3) . . ?
C18 C16 O4 116.0(3) . . ?
C9 C8 C13 118.4(3) . . ?
C9 C8 C7 120.7(3) . . ?
C13 C8 C7 120.9(3) . . ?
O3 C22 O4 123.1(3) . . ?
O3 C22 C15 128.1(3) . . ?
O4 C22 C15 108.8(2) . . ?
O2 C5 O1 126.4(3) . . ?
O2 C5 N1 124.8(3) . . ?
O1 C5 N1 108.8(3) . . ?
C16 C17 C20 118.5(3) . . ?
C16 C17 H17 120.8 . . ?
C20 C17 H17 120.8 . . ?
C14 C15 C22 122.7(3) . . ?
C14 C15 H15 118.7 . . ?
C22 C15 H15 118.7 . . ?
C19 C21 C20 122.5(3) . . ?
C19 C21 N2 118.8(3) . . ?
C20 C21 N2 118.7(3) . . ?
C8 C9 C10 121.4(3) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C21 C20 C17 118.9(3) . . ?
C21 C20 H20 120.5 . . ?
C17 C20 H20 120.5 . . ?
N1 C6 C14 112.9(2) . . ?
N1 C6 C7 109.6(2) . . ?
C14 C6 C7 108.1(2) . . ?
N1 C6 H6 108.7 . . ?
C14 C6 H6 108.7 . . ?
C7 C6 H6 108.7 . . ?
C15 C14 C6 124.8(3) . . ?
C15 C14 H14 117.6 . . ?
C6 C14 H14 117.6 . . ?
C19 C18 C16 119.3(3) . . ?
C19 C18 H18 120.3 . . ?
C16 C18 H18 120.3 . . ?
C8 C7 C6 115.7(2) . . ?
C8 C7 H7A 108.4 . . ?
C6 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.4 . . ?
C12 C13 C8 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C18 C19 C21 118.4(3) . . ?
C18 C19 H19 120.8 . . ?
C21 C19 H19 120.8 . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
O1 C2 C1 101.7(3) . . ?
O1 C2 C3 109.7(2) . . ?
C1 C2 C3 110.8(3) . . ?
O1 C2 C4 109.9(3) . . ?
C1 C2 C4 111.2(3) . . ?
C3 C2 C4 112.9(3) . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_Monc1_a
_database_code_depnum_ccdc_archive 'CCDC 2225785'
loop_
_audit_author_name
_audit_author_address
'MANJEET SINGH'
;Indian Institute of Science Education and Research Pune
India
;
_audit_update_record             
;
2022-12-12 deposited with the CCDC.	2023-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 N O3'
_chemical_formula_sum            C16H19NO3
_chemical_formula_weight         273.32

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.146(3)
_cell_length_b                   14.129(7)
_cell_length_c                   16.674(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.499(14)
_cell_angle_gamma                90
_cell_volume                     1427.9(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3576
_cell_measurement_theta_min      1.900
_cell_measurement_theta_max      28.476

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             584.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.088
_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      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20509
_diffrn_reflns_av_unetI/netI     0.1905
_diffrn_reflns_av_R_equivalents  0.1952
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.900
_diffrn_reflns_theta_max         28.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3576
_reflns_number_gt                1499
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1585P)²+1.7248P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.048(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3576
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1915
_refine_ls_R_factor_gt           0.0723
_refine_ls_wR_factor_ref         0.2710
_refine_ls_wR_factor_gt          0.1772
_refine_ls_goodness_of_fit_ref   0.790
_refine_ls_restrained_S_all      0.790
_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 0.4987(4) 0.67066(18) 0.72517(15) 0.0255(7) Uani 1 1 d . . . . .
O3 O 0.0563(5) 0.86609(19) 0.59855(17) 0.0311(7) Uani 1 1 d . . . . .
O2 O 0.1334(5) 0.7112(2) 0.70536(17) 0.0311(7) Uani 1 1 d . . . . .
N1 N 0.3786(5) 0.7744(2) 0.62887(19) 0.0251(8) Uani 1 1 d . . . . .
C5 C 0.3176(7) 0.7174(3) 0.6898(2) 0.0251(9) Uani 1 1 d . . . . .
C7 C 0.3758(7) 0.8918(3) 0.5344(2) 0.0262(9) Uani 1 1 d . . . . .
H7 H 0.328379 0.942024 0.499898 0.031 Uiso 1 1 calc R U . . .
C8 C 0.5733(7) 0.8520(3) 0.5415(2) 0.0271(9) Uani 1 1 d . . . . .
H8 H 0.684271 0.871583 0.513478 0.032 Uiso 1 1 calc R U . . .
C6 C 0.2424(7) 0.8460(3) 0.5883(2) 0.0269(9) Uani 1 1 d . . . . .
C9 C 0.5942(7) 0.7709(3) 0.6008(2) 0.0259(9) Uani 1 1 d . . . . .
H9 H 0.712879 0.783814 0.646385 0.031 Uiso 1 1 calc R U . . .
C14 C 0.1422(7) 0.6293(3) 0.3500(3) 0.0294(10) Uani 1 1 d . . . . .
H14 H 0.031985 0.622117 0.304966 0.035 Uiso 1 1 calc R U . . .
C3 C 0.4786(7) 0.5888(3) 0.7800(2) 0.0259(9) Uani 1 1 d . . . . .
C11 C 0.4686(7) 0.6552(3) 0.4860(2) 0.0251(9) Uani 1 1 d . . . . .
C2 C 0.7173(7) 0.5557(3) 0.8002(2) 0.0289(10) Uani 1 1 d . . . . .
H2A H 0.769272 0.538432 0.750978 0.043 Uiso 1 1 calc R U . . .
H2B H 0.726084 0.501852 0.835717 0.043 Uiso 1 1 calc R U . . .
H2C H 0.806964 0.605938 0.826621 0.043 Uiso 1 1 calc R U . . .
C16 C 0.5034(7) 0.6832(3) 0.4092(2) 0.0286(10) Uani 1 1 d . . . . .
H16 H 0.637329 0.710697 0.403259 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6389(7) 0.6766(3) 0.5599(2) 0.0265(9) Uani 1 1 d . . . . .
H10A H 0.783600 0.679262 0.543950 0.032 Uiso 1 1 calc R U . . .
H10B H 0.640249 0.625668 0.598978 0.032 Uiso 1 1 calc R U . . .
C12 C 0.2692(7) 0.6114(3) 0.4935(3) 0.0293(10) Uani 1 1 d . . . . .
H12 H 0.244856 0.590598 0.544186 0.035 Uiso 1 1 calc R U . . .
C4 C 0.3347(7) 0.5135(3) 0.7329(3) 0.0308(10) Uani 1 1 d . . . . .
H4A H 0.186581 0.536793 0.718870 0.046 Uiso 1 1 calc R U . . .
H4B H 0.335081 0.457680 0.765737 0.046 Uiso 1 1 calc R U . . .
H4C H 0.391441 0.498310 0.684107 0.046 Uiso 1 1 calc R U . . .
C15 C 0.3413(7) 0.6709(3) 0.3410(2) 0.0304(10) Uani 1 1 d . . . . .
H15 H 0.366312 0.690326 0.290022 0.036 Uiso 1 1 calc R U . . .
C13 C 0.1066(7) 0.5985(3) 0.4257(3) 0.0295(10) Uani 1 1 d . . . . .
H13 H -0.025741 0.569306 0.431165 0.035 Uiso 1 1 calc R U . . .
C1 C 0.3945(7) 0.6208(3) 0.8564(2) 0.0296(10) Uani 1 1 d . . . . .
H1A H 0.482503 0.672672 0.880605 0.044 Uiso 1 1 calc R U . . .
H1B H 0.404198 0.569197 0.894322 0.044 Uiso 1 1 calc R U . . .
H1C H 0.243547 0.640605 0.842506 0.044 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 C5 1.343(4) . ?
O1 C3 1.493(5) . ?
O3 C6 1.218(5) . ?
O2 C5 1.206(5) . ?
N1 C5 1.396(5) . ?
N1 C6 1.412(5) . ?
N1 C9 1.477(5) . ?
C7 C8 1.325(6) . ?
C7 C6 1.463(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.505(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.541(5) . ?
C9 H9 0.9800 . ?
C14 C13 1.386(6) . ?
C14 C15 1.387(6) . ?
C14 H14 0.9300 . ?
C3 C4 1.518(5) . ?
C3 C1 1.520(6) . ?
C3 C2 1.524(6) . ?
C11 C16 1.390(6) . ?
C11 C12 1.397(6) . ?
C11 C10 1.510(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C16 C15 1.394(5) . ?
C16 H16 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C13 1.391(6) . ?
C12 H12 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C15 H15 0.9300 . ?
C13 H13 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C3 120.2(3) . . ?
C5 N1 C6 123.6(4) . . ?
C5 N1 C9 125.0(3) . . ?
C6 N1 C9 111.4(3) . . ?
O2 C5 O1 127.6(4) . . ?
O2 C5 N1 124.9(4) . . ?
O1 C5 N1 107.5(4) . . ?
C8 C7 C6 110.8(4) . . ?
C8 C7 H7 124.6 . . ?
C6 C7 H7 124.6 . . ?
C7 C8 C9 111.0(4) . . ?
C7 C8 H8 124.5 . . ?
C9 C8 H8 124.5 . . ?
O3 C6 N1 126.6(4) . . ?
O3 C6 C7 128.1(4) . . ?
N1 C6 C7 105.3(3) . . ?
N1 C9 C8 101.5(3) . . ?
N1 C9 C10 113.9(3) . . ?
C8 C9 C10 111.7(3) . . ?
N1 C9 H9 109.9 . . ?
C8 C9 H9 109.9 . . ?
C10 C9 H9 109.9 . . ?
C13 C14 C15 120.4(4) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
O1 C3 C4 109.0(3) . . ?
O1 C3 C1 110.9(3) . . ?
C4 C3 C1 113.1(4) . . ?
O1 C3 C2 101.5(3) . . ?
C4 C3 C2 110.9(3) . . ?
C1 C3 C2 110.8(3) . . ?
C16 C11 C12 118.6(4) . . ?
C16 C11 C10 120.2(4) . . ?
C12 C11 C10 121.1(4) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C11 C16 C15 121.2(4) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C11 C10 C9 112.6(3) . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C11 C12 C13 120.6(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C16 C15 C14 119.3(4) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C14 C13 C12 119.9(4) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.081

