# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rml713a_0m
_database_code_depnum_ccdc_archive 'CCDC 1832647'
loop_
_audit_author_name
_audit_author_address
'Dilip K Maiti'
;University of Calcutta
India
;
_audit_update_record             
;
2018-03-26 deposited with the CCDC.	2024-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N2 O2'
_chemical_formula_sum            'C16 H18 N2 O2'
_chemical_formula_weight         270.14

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.827(4)
_cell_length_b                   10.029(4)
_cell_length_c                   17.446(8)
_cell_angle_alpha                89.147(6)
_cell_angle_beta                 87.469(6)
_cell_angle_gamma                82.695(6)
_cell_volume                     1356.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1611
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      21.50

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.88
_exptl_crystal_size_mid          0.66
_exptl_crystal_size_min          0.44
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             604
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9449
_exptl_absorpt_correction_T_max  0.9698
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8425
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.17
_diffrn_reflns_theta_max         30.60
_reflns_number_total             3994
_reflns_number_gt                2746
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0538P)²+0.1255P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3994
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1240
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.050
_refine_ls_shift/su_mean         0.004

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6350(2) 0.61816(19) 0.72712(11) 0.0734(6) Uani 1 1 d . . .
O2 O 0.3192(2) 0.97761(17) 0.62207(10) 0.0685(6) Uani 1 1 d . . .
O3 O 0.8528(2) 0.34886(19) 0.29316(11) 0.0754(6) Uani 1 1 d . . .
O4 O 1.1911(2) 0.33019(17) 0.07559(11) 0.0703(6) Uani 1 1 d . . .
N1 N 0.4854(2) 0.81458(19) 0.68667(11) 0.0486(5) Uani 1 1 d . . .
N2 N 0.5969(2) 0.66016(18) 0.47303(11) 0.0447(5) Uani 1 1 d . . .
N3 N 1.0130(3) 0.31312(19) 0.18085(12) 0.0524(6) Uani 1 1 d . . .
N4 N 0.9063(2) 0.71909(18) 0.15492(11) 0.0479(5) Uani 1 1 d . . .
C1 C 0.1113(4) 0.8910(3) 0.31648(18) 0.0667(8) Uani 1 1 d . . .
H1 H 0.0293 0.9130 0.2799 0.080 Uiso 1 1 calc R . .
C2 C 0.1103(3) 0.9677(3) 0.38144(18) 0.0642(8) Uani 1 1 d . . .
H2 H 0.0280 1.0424 0.3886 0.077 Uiso 1 1 calc R . .
C3 C 0.2316(3) 0.9336(2) 0.43579(15) 0.0538(7) Uani 1 1 d . . .
H3 H 0.2315 0.9868 0.4790 0.065 Uiso 1 1 calc R . .
C4 C 0.3537(3) 0.8213(2) 0.42699(14) 0.0433(6) Uani 1 1 d . . .
C5 C 0.4796(3) 0.7841(2) 0.48959(13) 0.0411(6) Uani 1 1 d . . .
H5 H 0.5484 0.8580 0.4956 0.049 Uiso 1 1 calc R . .
C6 C 0.3934(3) 0.7538(2) 0.56807(13) 0.0408(6) Uani 1 1 d . . .
H6 H 0.2767 0.7314 0.5615 0.049 Uiso 1 1 calc R . .
C7 C 0.3900(3) 0.8635(2) 0.62590(14) 0.0464(6) Uani 1 1 d . . .
C8 C 0.5111(4) 0.8953(3) 0.75275(16) 0.0764(9) Uani 1 1 d . . .
H8A H 0.5519 0.8374 0.7941 0.115 Uiso 1 1 calc R . .
H8B H 0.4037 0.9469 0.7685 0.115 Uiso 1 1 calc R . .
H8C H 0.5944 0.9551 0.7392 0.115 Uiso 1 1 calc R . .
C9 C 0.5520(3) 0.6820(3) 0.67929(15) 0.0508(7) Uani 1 1 d . . .
C10 C 0.5058(3) 0.6345(2) 0.60274(13) 0.0439(6) Uani 1 1 d . . .
H10 H 0.4426 0.5564 0.6086 0.053 Uiso 1 1 calc R . .
C11 C 0.6608(3) 0.6052(2) 0.54637(13) 0.0442(6) Uani 1 1 d . . .
H11 H 0.6927 0.5078 0.5421 0.053 Uiso 1 1 calc R . .
C12 C 0.2336(4) 0.7826(3) 0.30649(16) 0.0656(8) Uani 1 1 d . . .
H12 H 0.2365 0.7319 0.2622 0.079 Uiso 1 1 calc R . .
C13 C 0.3536(3) 0.7471(2) 0.36143(15) 0.0556(7) Uani 1 1 d . . .
H13 H 0.4352 0.6721 0.3539 0.067 Uiso 1 1 calc R . .
C14 C 0.7520(3) 0.6819(2) 0.42648(15) 0.0561(7) Uani 1 1 d . . .
H14A H 0.7296 0.7629 0.3955 0.067 Uiso 1 1 calc R . .
H14B H 0.7850 0.6066 0.3924 0.067 Uiso 1 1 calc R . .
C15 C 0.8964(3) 0.6955(3) 0.48069(17) 0.0696(8) Uani 1 1 d . . .
H15A H 0.9953 0.6293 0.4691 0.084 Uiso 1 1 calc R . .
H15B H 0.9324 0.7845 0.4764 0.084 Uiso 1 1 calc R . .
C16 C 0.8207(3) 0.6722(2) 0.56031(15) 0.0553(7) Uani 1 1 d . . .
H16A H 0.7902 0.7566 0.5870 0.066 Uiso 1 1 calc R . .
H16B H 0.9016 0.6140 0.5903 0.066 Uiso 1 1 calc R . .
C17 C 1.3788(4) 0.8375(3) -0.03014(17) 0.0722(9) Uani 1 1 d . . .
H17 H 1.4568 0.8823 -0.0591 0.087 Uiso 1 1 calc R . .
C18 C 1.2658(4) 0.9058(3) 0.02119(18) 0.0722(8) Uani 1 1 d . . .
H18 H 1.2667 0.9977 0.0273 0.087 Uiso 1 1 calc R . .
C19 C 1.1502(3) 0.8400(3) 0.06430(16) 0.0608(7) Uani 1 1 d . . .
H19 H 1.0735 0.8883 0.0991 0.073 Uiso 1 1 calc R . .
C20 C 1.1462(3) 0.7046(2) 0.05679(13) 0.0439(6) Uani 1 1 d . . .
C21 C 1.0216(3) 0.6299(2) 0.10382(13) 0.0419(6) Uani 1 1 d . . .
H21 H 0.9516 0.5863 0.0689 0.050 Uiso 1 1 calc R . .
C22 C 1.1081(3) 0.5226(2) 0.15896(13) 0.0426(6) Uani 1 1 d . . .
H22 H 1.2239 0.5419 0.1702 0.051 Uiso 1 1 calc R . .
C23 C 1.1140(3) 0.3813(2) 0.13143(15) 0.0492(7) Uani 1 1 d . . .
C24 C 0.9889(4) 0.1736(2) 0.17064(18) 0.0755(9) Uani 1 1 d . . .
H24A H 0.9432 0.1630 0.1212 0.113 Uiso 1 1 calc R . .
H24B H 0.9098 0.1474 0.2100 0.113 Uiso 1 1 calc R . .
H24C H 1.0976 0.1180 0.1740 0.113 Uiso 1 1 calc R . .
C25 C 0.9413(3) 0.3898(3) 0.24191(16) 0.0527(7) Uani 1 1 d . . .
C26 C 1.3770(4) 0.7026(3) -0.03895(16) 0.0685(8) Uani 1 1 d . . .
H26 H 1.4541 0.6553 -0.0739 0.082 Uiso 1 1 calc R . .
C27 C 1.2609(3) 0.6363(3) 0.00404(14) 0.0566(7) Uani 1 1 d . . .
H27 H 1.2599 0.5446 -0.0026 0.068 Uiso 1 1 calc R . .
C28 C 0.8420(3) 0.6373(2) 0.21743(13) 0.0489(7) Uani 1 1 d . . .
H28 H 0.8170 0.6927 0.2634 0.059 Uiso 1 1 calc R . .
C29 C 0.6753(3) 0.5955(3) 0.19014(17) 0.0652(8) Uani 1 1 d . . .
H29A H 0.6973 0.5178 0.1570 0.078 Uiso 1 1 calc R . .
H29B H 0.5992 0.5755 0.2330 0.078 Uiso 1 1 calc R . .
C30 C 0.6012(4) 0.7185(3) 0.1467(2) 0.0928(11) Uani 1 1 d . . .
H30A H 0.5363 0.6935 0.1042 0.111 Uiso 1 1 calc R . .
H30B H 0.5251 0.7781 0.1801 0.111 Uiso 1 1 calc R . .
C31 C 0.7511(3) 0.7854(3) 0.11797(16) 0.0653(8) Uani 1 1 d . . .
H31A H 0.7655 0.7772 0.0627 0.078 Uiso 1 1 calc R . .
H31B H 0.7325 0.8801 0.1306 0.078 Uiso 1 1 calc R . .
C32 C 0.9931(3) 0.5283(2) 0.23194(13) 0.0454(6) Uani 1 1 d . . .
H32 H 1.0566 0.5515 0.2760 0.054 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.206(3) . ?
O2 C7 1.209(3) . ?
O3 C25 1.206(3) . ?
O4 C23 1.208(3) . ?
N1 C9 1.371(3) . ?
N1 C7 1.373(3) . ?
N1 C8 1.454(3) . ?
N2 C11 1.468(3) . ?
N2 C14 1.469(3) . ?
N2 C5 1.472(3) . ?
N3 C23 1.376(3) . ?
N3 C25 1.380(3) . ?
N3 C24 1.450(3) . ?
N4 C28 1.464(3) . ?
N4 C21 1.468(3) . ?
N4 C31 1.478(3) . ?
C1 C12 1.362(4) . ?
C1 C2 1.378(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C13 1.374(3) . ?
C4 C5 1.514(3) . ?
C5 C6 1.542(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.501(3) . ?
C6 C10 1.526(3) . ?
C6 H6 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.499(3) . ?
C10 C11 1.529(3) . ?
C10 H10 0.9800 . ?
C11 C16 1.524(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.526(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.513(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.359(4) . ?
C17 C26 1.366(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.371(3) . ?
C19 H19 0.9300 . ?
C20 C27 1.382(3) . ?
C20 C21 1.511(3) . ?
C21 C22 1.544(3) . ?
C21 H21 0.9800 . ?
C22 C23 1.498(3) . ?
C22 C32 1.524(3) . ?
C22 H22 0.9800 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C32 1.501(3) . ?
C26 C27 1.382(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.519(3) . ?
C28 C32 1.532(3) . ?
C28 H28 0.9800 . ?
C29 C30 1.504(4) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.489(4) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C7 113.4(2) . . ?
C9 N1 C8 123.5(2) . . ?
C7 N1 C8 123.1(2) . . ?
C11 N2 C14 105.09(18) . . ?
C11 N2 C5 107.63(17) . . ?
C14 N2 C5 113.96(18) . . ?
C23 N3 C25 113.2(2) . . ?
C23 N3 C24 123.2(2) . . ?
C25 N3 C24 123.6(2) . . ?
C28 N4 C21 108.17(17) . . ?
C28 N4 C31 105.49(19) . . ?
C21 N4 C31 113.91(19) . . ?
C12 C1 C2 119.3(3) . . ?
C12 C1 H1 120.3 . . ?
C2 C1 H1 120.3 . . ?
C1 C2 C3 119.9(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C13 C4 C3 118.0(2) . . ?
C13 C4 C5 122.6(2) . . ?
C3 C4 C5 119.4(2) . . ?
N2 C5 C4 112.89(18) . . ?
N2 C5 C6 103.40(17) . . ?
C4 C5 C6 114.09(18) . . ?
N2 C5 H5 108.7 . . ?
C4 C5 H5 108.7 . . ?
C6 C5 H5 108.7 . . ?
C7 C6 C10 104.47(19) . . ?
C7 C6 C5 114.46(19) . . ?
C10 C6 C5 106.66(17) . . ?
C7 C6 H6 110.3 . . ?
C10 C6 H6 110.3 . . ?
C5 C6 H6 110.3 . . ?
O2 C7 N1 123.4(2) . . ?
O2 C7 C6 128.0(2) . . ?
N1 C7 C6 108.62(19) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 N1 124.2(2) . . ?
O1 C9 C10 127.4(2) . . ?
N1 C9 C10 108.3(2) . . ?
C9 C10 C6 105.12(19) . . ?
C9 C10 C11 113.4(2) . . ?
C6 C10 C11 105.29(18) . . ?
C9 C10 H10 110.9 . . ?
C6 C10 H10 110.9 . . ?
C11 C10 H10 110.9 . . ?
N2 C11 C16 105.80(19) . . ?
N2 C11 C10 104.02(17) . . ?
C16 C11 C10 117.80(19) . . ?
N2 C11 H11 109.6 . . ?
C16 C11 H11 109.6 . . ?
C10 C11 H11 109.6 . . ?
C1 C12 C13 120.8(3) . . ?
C1 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C4 C13 C12 120.8(2) . . ?
C4 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
N2 C14 C15 108.2(2) . . ?
N2 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
N2 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
C16 C15 C14 105.4(2) . . ?
C16 C15 H15A 110.7 . . ?
C14 C15 H15A 110.7 . . ?
C16 C15 H15B 110.7 . . ?
C14 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
C15 C16 C11 104.2(2) . . ?
C15 C16 H16A 110.9 . . ?
C11 C16 H16A 110.9 . . ?
C15 C16 H16B 110.9 . . ?
C11 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
C18 C17 C26 119.5(3) . . ?
C18 C17 H17 120.2 . . ?
C26 C17 H17 120.2 . . ?
C17 C18 C19 120.5(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 121.1(3) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C27 117.9(2) . . ?
C19 C20 C21 122.1(2) . . ?
C27 C20 C21 120.0(2) . . ?
N4 C21 C20 112.45(19) . . ?
N4 C21 C22 103.47(18) . . ?
C20 C21 C22 114.41(18) . . ?
N4 C21 H21 108.8 . . ?
C20 C21 H21 108.8 . . ?
C22 C21 H21 108.8 . . ?
C23 C22 C32 104.65(19) . . ?
C23 C22 C21 114.03(19) . . ?
C32 C22 C21 106.36(17) . . ?
C23 C22 H22 110.5 . . ?
C32 C22 H22 110.5 . . ?
C21 C22 H22 110.5 . . ?
O4 C23 N3 123.1(2) . . ?
O4 C23 C22 128.2(2) . . ?
N3 C23 C22 108.7(2) . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O3 C25 N3 124.2(3) . . ?
O3 C25 C32 127.8(2) . . ?
N3 C25 C32 108.0(2) . . ?
C17 C26 C27 120.1(3) . . ?
C17 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C20 120.9(3) . . ?
C26 C27 H27 119.6 . . ?
C20 C27 H27 119.6 . . ?
N4 C28 C29 105.4(2) . . ?
N4 C28 C32 104.32(18) . . ?
C29 C28 C32 118.8(2) . . ?
N4 C28 H28 109.3 . . ?
C29 C28 H28 109.3 . . ?
C32 C28 H28 109.3 . . ?
C30 C29 C28 102.1(2) . . ?
C30 C29 H29A 111.3 . . ?
C28 C29 H29A 111.3 . . ?
C30 C29 H29B 111.3 . . ?
C28 C29 H29B 111.3 . . ?
H29A C29 H29B 109.2 . . ?
C31 C30 C29 106.0(2) . . ?
C31 C30 H30A 110.5 . . ?
C29 C30 H30A 110.5 . . ?
C31 C30 H30B 110.5 . . ?
C29 C30 H30B 110.5 . . ?
H30A C30 H30B 108.7 . . ?
N4 C31 C30 108.0(2) . . ?
N4 C31 H31A 110.1 . . ?
C30 C31 H31A 110.1 . . ?
N4 C31 H31B 110.1 . . ?
C30 C31 H31B 110.1 . . ?
H31A C31 H31B 108.4 . . ?
C25 C32 C22 105.39(19) . . ?
C25 C32 C28 113.8(2) . . ?
C22 C32 C28 105.78(18) . . ?
C25 C32 H32 110.5 . . ?
C22 C32 H32 110.5 . . ?
C28 C32 H32 110.5 . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        30.60
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.033
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.041
;
####################################################################### 
# 
# 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_mo_NRJ161123_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2312186'
loop_
_audit_author_name
_audit_author_address
'Dilip K Maiti'
;University of Calcutta
India
;
_audit_update_record             
;
2023-12-05 deposited with the CCDC.	2024-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 F N2 O2'
_chemical_formula_weight         378.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 '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'
H H 0.0000 0.0000 '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                   19.48(2)
_cell_length_b                   5.587(5)
_cell_length_c                   18.462(17)
_cell_angle_alpha                90
_cell_angle_beta                 101.83(3)
_cell_angle_gamma                90
_cell_volume                     1967(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2521
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      30.90

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   0.400300
_exptl_transmission_factor_max   0.746600
_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   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(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            18701
_diffrn_reflns_av_unetI/netI     0.2134
_diffrn_reflns_av_R_equivalents  0.1364
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.068
_diffrn_reflns_theta_max         33.512
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             6786
_reflns_number_gt                2096
_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-2016/6 (Sheldrick, 2016)'
_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)+(0.1000P)²+0.2427P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6786
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2871
_refine_ls_R_factor_gt           0.1224
_refine_ls_wR_factor_ref         0.3250
_refine_ls_wR_factor_gt          0.2449
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.24275(12) 0.9677(4) 0.73817(19) 0.0620(9) Uani 1 1 d . . . . .
N1 N 0.29718(13) 0.4906(4) 0.57538(19) 0.0476(8) Uani 1 1 d . . . . .
F1 F 0.47887(13) 0.5789(5) 0.9035(2) 0.0944(9) Uani 1 1 d . . . . .
N2 N 0.16940(13) 0.6718(4) 0.6795(2) 0.0544(9) Uani 1 1 d . . . . .
C9 C 0.36140(14) 0.6740(5) 0.6914(2) 0.0439(9) Uani 1 1 d . . . . .
O1 O 0.11478(16) 0.3919(6) 0.5948(2) 0.1070(14) Uani 1 1 d . . . . .
C8 C 0.31856(15) 0.7152(4) 0.6157(2) 0.0442(9) Uani 1 1 d . . . . .
H8 H 0.346717 0.808283 0.587507 0.053 Uiso 1 1 calc R U . . .
C16 C 0.22205(16) 0.8458(5) 0.6845(3) 0.0515(11) Uani 1 1 d . . . . .
C10 C 0.35060(17) 0.4747(5) 0.7340(3) 0.0530(11) Uani 1 1 d . . . . .
H10 H 0.316640 0.362374 0.714407 0.064 Uiso 1 1 calc R U . . .
C11 C 0.3895(2) 0.4436(6) 0.8042(3) 0.0612(12) Uani 1 1 d . . . . .
H11 H 0.382016 0.309904 0.831621 0.073 Uiso 1 1 calc R U . . .
C14 C 0.41284(16) 0.8372(5) 0.7239(3) 0.0543(11) Uani 1 1 d . . . . .
H14 H 0.421091 0.970503 0.696759 0.065 Uiso 1 1 calc R U . . .
C7 C 0.24616(15) 0.8489(5) 0.6115(2) 0.0524(11) Uani 1 1 d . . . . .
H7 H 0.247925 1.012531 0.592898 0.063 Uiso 1 1 calc R U . . .
C5 C 0.23511(17) 0.5383(5) 0.5172(3) 0.0568(11) Uani 1 1 d . . . . .
H5 H 0.209674 0.388351 0.503383 0.068 Uiso 1 1 calc R U . . .
C17 C 0.13574(16) 0.6179(5) 0.7405(3) 0.0533(11) Uani 1 1 d . . . . .
C18 C 0.08603(17) 0.7757(5) 0.7569(3) 0.0607(12) Uani 1 1 d . . . . .
H18 H 0.074903 0.914427 0.729197 0.073 Uiso 1 1 calc R U . . .
C12 C 0.43972(18) 0.6105(7) 0.8344(3) 0.0628(12) Uani 1 1 d . . . . .
C22 C 0.15234(19) 0.4135(6) 0.7822(3) 0.0652(13) Uani 1 1 d . . . . .
H22 H 0.185796 0.307761 0.771529 0.078 Uiso 1 1 calc R U . . .
C19 C 0.05307(18) 0.7250(6) 0.8150(3) 0.0668(14) Uani 1 1 d . . . . .
H19 H 0.019744 0.831146 0.825764 0.080 Uiso 1 1 calc R U . . .
C6 C 0.19258(17) 0.6978(6) 0.5591(3) 0.0609(12) Uani 1 1 d . . . . .
H6 H 0.160112 0.799611 0.524821 0.073 Uiso 1 1 calc R U . . .
C13 C 0.45178(18) 0.8087(6) 0.7944(3) 0.0667(13) Uani 1 1 d . . . . .
H13 H 0.485561 0.920888 0.814620 0.080 Uiso 1 1 calc R U . . .
C1 C 0.35486(18) 0.3715(5) 0.5477(3) 0.0604(12) Uani 1 1 d . . . . .
H1A H 0.341644 0.206666 0.535552 0.072 Uiso 1 1 calc R U . . .
H1B H 0.396383 0.369451 0.587034 0.072 Uiso 1 1 calc R U . . .
C2 C 0.3731(2) 0.4917(6) 0.4795(3) 0.0691(13) Uani 1 1 d . . . . .
H2A H 0.393593 0.647760 0.493083 0.083 Uiso 1 1 calc R U . . .
H2B H 0.407505 0.395617 0.461362 0.083 Uiso 1 1 calc R U . . .
C15 C 0.15399(18) 0.5624(6) 0.6110(3) 0.0670(13) Uani 1 1 d . . . . .
C21 C 0.1190(2) 0.3669(6) 0.8397(3) 0.0702(14) Uani 1 1 d . . . . .
H21 H 0.130518 0.228733 0.867683 0.084 Uiso 1 1 calc R U . . .
C4 C 0.25120(19) 0.6584(6) 0.4474(3) 0.0645(12) Uani 1 1 d . . . . .
H4A H 0.208890 0.663668 0.409089 0.077 Uiso 1 1 calc R U . . .
H4B H 0.266729 0.821513 0.458815 0.077 Uiso 1 1 calc R U . . .
C20 C 0.06857(18) 0.5210(6) 0.8572(3) 0.0628(12) Uani 1 1 d . . . . .
C3 C 0.3082(2) 0.5197(6) 0.4191(3) 0.0727(14) Uani 1 1 d . . . . .
H3A H 0.290478 0.362870 0.402091 0.087 Uiso 1 1 calc R U . . .
H3B H 0.320165 0.604071 0.377482 0.087 Uiso 1 1 calc R U . . .
C23 C 0.0329(2) 0.4628(8) 0.9220(3) 0.0953(18) Uani 1 1 d . . . . .
H23A H 0.026961 0.607402 0.948099 0.143 Uiso 1 1 calc R U . . .
H23B H 0.061644 0.353024 0.955066 0.143 Uiso 1 1 calc R U . . .
H23C H -0.012044 0.391563 0.903327 0.143 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
O2 C16 1.202(5) . ?
N1 C5 1.468(5) . ?
N1 C8 1.475(4) . ?
N1 C1 1.484(4) . ?
F1 C12 1.358(6) . ?
N2 C15 1.382(6) . ?
N2 C16 1.403(4) . ?
N2 C17 1.446(5) . ?
C9 C14 1.396(5) . ?
C9 C10 1.403(5) . ?
C9 C8 1.492(5) . ?
O1 C15 1.219(4) . ?
C8 C7 1.584(4) . ?
C8 H8 0.9800 . ?
C16 C7 1.515(6) . ?
C10 C11 1.371(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(6) . ?
C11 H11 0.9300 . ?
C14 C13 1.374(6) . ?
C14 H14 0.9300 . ?
C7 C6 1.525(5) . ?
C7 H7 0.9800 . ?
C5 C6 1.530(5) . ?
C5 C4 1.542(6) . ?
C5 H5 0.9800 . ?
C17 C22 1.378(5) . ?
C17 C18 1.389(4) . ?
C18 C19 1.388(6) . ?
C18 H18 0.9300 . ?
C12 C13 1.378(6) . ?
C22 C21 1.380(6) . ?
C22 H22 0.9300 . ?
C19 C20 1.379(6) . ?
C19 H19 0.9300 . ?
C6 C15 1.533(6) . ?
C6 H6 0.9800 . ?
C13 H13 0.9300 . ?
C1 C2 1.532(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.514(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C21 C20 1.393(5) . ?
C21 H21 0.9300 . ?
C4 C3 1.530(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C20 C23 1.535(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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 N1 C8 108.7(2) . . ?
C5 N1 C1 113.5(3) . . ?
C8 N1 C1 113.6(2) . . ?
C15 N2 C16 112.7(3) . . ?
C15 N2 C17 124.9(3) . . ?
C16 N2 C17 122.4(3) . . ?
C14 C9 C10 117.0(4) . . ?
C14 C9 C8 121.1(3) . . ?
C10 C9 C8 121.9(3) . . ?
N1 C8 C9 112.8(2) . . ?
N1 C8 C7 102.7(2) . . ?
C9 C8 C7 116.1(3) . . ?
N1 C8 H8 108.3 . . ?
C9 C8 H8 108.3 . . ?
C7 C8 H8 108.3 . . ?
O2 C16 N2 124.4(4) . . ?
O2 C16 C7 127.9(3) . . ?
N2 C16 C7 107.8(3) . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.2(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C14 C9 122.6(3) . . ?
C13 C14 H14 118.7 . . ?
C9 C14 H14 118.7 . . ?
C16 C7 C6 105.2(3) . . ?
C16 C7 C8 112.7(3) . . ?
C6 C7 C8 104.9(2) . . ?
C16 C7 H7 111.2 . . ?
C6 C7 H7 111.2 . . ?
C8 C7 H7 111.2 . . ?
N1 C5 C6 100.7(4) . . ?
N1 C5 C4 114.4(3) . . ?
C6 C5 C4 113.2(3) . . ?
N1 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
C4 C5 H5 109.4 . . ?
C22 C17 C18 119.9(4) . . ?
C22 C17 N2 121.0(3) . . ?
C18 C17 N2 119.1(3) . . ?
C19 C18 C17 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
F1 C12 C13 118.9(4) . . ?
F1 C12 C11 120.4(4) . . ?
C13 C12 C11 120.7(5) . . ?
C17 C22 C21 119.5(3) . . ?
C17 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C20 C19 C18 121.5(3) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C7 C6 C5 105.8(3) . . ?
C7 C6 C15 103.7(4) . . ?
C5 C6 C15 114.4(3) . . ?
C7 C6 H6 110.9 . . ?
C5 C6 H6 110.9 . . ?
C15 C6 H6 110.9 . . ?
C14 C13 C12 118.6(4) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
N1 C1 C2 114.0(3) . . ?
N1 C1 H1A 108.8 . . ?
C2 C1 H1A 108.8 . . ?
N1 C1 H1B 108.8 . . ?
C2 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 110.5(3) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
O1 C15 N2 125.3(4) . . ?
O1 C15 C6 126.6(5) . . ?
N2 C15 C6 108.1(3) . . ?
C22 C21 C20 121.8(4) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C3 C4 C5 110.5(3) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C19 C20 C21 117.6(4) . . ?
C19 C20 C23 122.2(3) . . ?
C21 C20 C23 120.1(4) . . ?
C2 C3 C4 110.9(4) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_refine_diff_density_max         0.412
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.107

