# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_aib
_database_code_depnum_ccdc_archive 'CCDC 2114931'
loop_
_audit_author_name
_audit_author_address
'Debasish Haldar'
;IISER Kolkata
India
;
_audit_update_record             
;
2021-10-11 deposited with the CCDC.	2022-05-10 downloaded from the CCDC.
;
_audit_creation_date             2021-08-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 N2 O3'
_chemical_formula_sum            'C18 H20 N2 O3'
_chemical_formula_weight         312.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.8282(6)
_cell_length_b                   10.4619(4)
_cell_length_c                   9.5748(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.788(4)
_cell_angle_gamma                90
_cell_volume                     1655.90(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3925
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0490
_cell_measurement_theta_min      2.2740
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.997
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8501
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.018
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_min         2.304
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00  17.00   1.00   30.00    --  -26.98 -77.00 120.00  131
  2  ω    -10.00 105.00   1.00   30.00    --   28.47  57.00  60.00  115
  3  ω    -48.00  67.00   1.00   30.00    --   28.47 -57.00-150.00  115
  4  ω    -55.00   1.00   1.00   30.00    --   28.47 -38.00   0.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2455
_reflns_number_total             2918
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2918
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0369P)²+0.7109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1128
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C11(H11), C5(H5), C1(H1A), C10(H10), C8(H8), C2(H2A), C4(H4),
 C3(H3), C9(H9)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21439(7) 0.79143(12) 0.25923(13) 0.0262(3) Uani 1 1 d . . . . .
O3 O 0.04140(7) 0.83592(12) 0.29481(14) 0.0279(3) Uani 1 1 d . . . . .
O2 O 0.07925(8) 1.02996(13) 0.23319(14) 0.0317(3) Uani 1 1 d . . . . .
N2 N 0.18348(8) 0.80561(14) 0.47625(15) 0.0203(3) Uani 1 1 d . . . . .
H2 H 0.1833 0.7700 0.5571 0.024 Uiso 1 1 calc R U . . .
N1 N 0.34618(9) 0.63634(16) 0.26636(16) 0.0296(4) Uani 1 1 d . . . . .
H1 H 0.3207 0.7055 0.2377 0.036 Uiso 1 1 calc R U . . .
C13 C 0.21342(9) 0.74141(17) 0.37749(18) 0.0208(4) Uani 1 1 d . . . . .
C12 C 0.24441(10) 0.60950(17) 0.41228(18) 0.0211(4) Uani 1 1 d . . . . .
C14 C 0.15102(10) 0.93488(17) 0.45067(18) 0.0211(4) Uani 1 1 d . . . . .
C17 C 0.08851(10) 0.93977(17) 0.31196(19) 0.0223(4) Uani 1 1 d . . . . .
C7 C 0.30833(10) 0.55937(18) 0.35121(19) 0.0242(4) Uani 1 1 d . . . . .
C6 C 0.41990(10) 0.61941(18) 0.21946(19) 0.0245(4) Uani 1 1 d . . . . .
C11 C 0.20640(10) 0.53197(17) 0.49818(19) 0.0248(4) Uani 1 1 d . . . . .
H11 H 0.1641 0.5653 0.5370 0.030 Uiso 1 1 calc R U . . .
C5 C 0.43054(11) 0.68685(18) 0.0995(2) 0.0274(4) Uani 1 1 d . . . . .
H5 H 0.3887 0.7375 0.0517 0.033 Uiso 1 1 calc R U . . .
C1 C 0.48372(11) 0.54555(19) 0.2905(2) 0.0292(4) Uani 1 1 d . . . . .
H1A H 0.4782 0.5010 0.3722 0.035 Uiso 1 1 calc R U . . .
C16 C 0.21833(11) 1.03081(18) 0.4433(2) 0.0293(4) Uani 1 1 d . . . . .
H16A H 0.2562 1.0304 0.5318 0.044 Uiso 1 1 calc R U . . .
H16B H 0.1955 1.1147 0.4262 0.044 Uiso 1 1 calc R U . . .
H16C H 0.2456 1.0077 0.3675 0.044 Uiso 1 1 calc R U . . .
C15 C 0.10790(11) 0.96937(18) 0.5729(2) 0.0281(4) Uani 1 1 d . . . . .
H15A H 0.0672 0.9064 0.5794 0.042 Uiso 1 1 calc R U . . .
H15B H 0.0829 1.0518 0.5554 0.042 Uiso 1 1 calc R U . . .
H15C H 0.1465 0.9715 0.6605 0.042 Uiso 1 1 calc R U . . .
C10 C 0.23006(11) 0.40682(18) 0.5271(2) 0.0301(4) Uani 1 1 d . . . . .
H10 H 0.2052 0.3567 0.5866 0.036 Uiso 1 1 calc R U . . .
C8 C 0.32960(11) 0.43068(18) 0.3780(2) 0.0303(5) Uani 1 1 d . . . . .
H8 H 0.3698 0.3943 0.3362 0.036 Uiso 1 1 calc R U . . .
C2 C 0.55522(11) 0.53839(19) 0.2399(2) 0.0338(5) Uani 1 1 d . . . . .
H2A H 0.5973 0.4881 0.2873 0.041 Uiso 1 1 calc R U . . .
C4 C 0.50225(11) 0.67977(19) 0.0502(2) 0.0346(5) Uani 1 1 d . . . . .
H4 H 0.5085 0.7256 -0.0302 0.042 Uiso 1 1 calc R U . . .
C3 C 0.56489(11) 0.60504(19) 0.1198(3) 0.0381(5) Uani 1 1 d . . . . .
H3 H 0.6131 0.5996 0.0860 0.046 Uiso 1 1 calc R U . . .
C18 C -0.02127(11) 0.8357(2) 0.1684(2) 0.0374(5) Uani 1 1 d . . . . .
H18A H 0.0032 0.8375 0.0855 0.056 Uiso 1 1 calc R U . . .
H18B H -0.0550 0.9097 0.1689 0.056 Uiso 1 1 calc R U . . .
H18C H -0.0535 0.7599 0.1671 0.056 Uiso 1 1 calc R U . . .
C9 C 0.29142(11) 0.35778(19) 0.4656(2) 0.0349(5) Uani 1 1 d . . . . .
H9 H 0.3074 0.2734 0.4838 0.042 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 C13 1.250(2) . ?
O3 C17 1.337(2) . ?
O3 C18 1.449(2) . ?
O2 C17 1.200(2) . ?
N2 H2 0.8600 . ?
N2 C13 1.333(2) . ?
N2 C14 1.462(2) . ?
N1 H1 0.8600 . ?
N1 C7 1.381(2) . ?
N1 C6 1.407(2) . ?
C13 C12 1.491(2) . ?
C12 C7 1.418(2) . ?
C12 C11 1.393(3) . ?
C14 C17 1.533(2) . ?
C14 C16 1.525(2) . ?
C14 C15 1.531(2) . ?
C7 C8 1.404(3) . ?
C6 C5 1.388(3) . ?
C6 C1 1.393(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.381(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.377(3) . ?
C1 H1A 0.9300 . ?
C1 C2 1.381(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C9 1.380(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.378(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.381(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.379(3) . ?
C3 H3 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C9 H9 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
C17 O3 C18 115.21(15) . . ?
C13 N2 H2 119.1 . . ?
C13 N2 C14 121.75(15) . . ?
C14 N2 H2 119.1 . . ?
C7 N1 H1 114.9 . . ?
C7 N1 C6 130.20(16) . . ?
C6 N1 H1 114.9 . . ?
O1 C13 N2 120.15(16) . . ?
O1 C13 C12 121.77(15) . . ?
N2 C13 C12 118.08(15) . . ?
C7 C12 C13 120.73(16) . . ?
C11 C12 C13 119.40(15) . . ?
C11 C12 C7 119.73(16) . . ?
N2 C14 C17 110.51(14) . . ?
N2 C14 C16 111.05(14) . . ?
N2 C14 C15 107.79(14) . . ?
C16 C14 C17 109.48(15) . . ?
C16 C14 C15 110.03(15) . . ?
C15 C14 C17 107.92(13) . . ?
O3 C17 C14 111.98(15) . . ?
O2 C17 O3 123.89(16) . . ?
O2 C17 C14 123.93(16) . . ?
N1 C7 C12 119.74(16) . . ?
N1 C7 C8 122.45(16) . . ?
C8 C7 C12 117.80(17) . . ?
C5 C6 N1 117.27(16) . . ?
C5 C6 C1 118.63(16) . . ?
C1 C6 N1 124.00(17) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 C12 121.54(17) . . ?
C10 C11 H11 119.2 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.87(17) . . ?
C4 C5 H5 119.6 . . ?
C6 C1 H1A 119.9 . . ?
C2 C1 C6 120.10(19) . . ?
C2 C1 H1A 119.9 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C10 H10 120.7 . . ?
C9 C10 C11 118.54(18) . . ?
C9 C10 H10 120.7 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.65(17) . . ?
C9 C8 H8 119.7 . . ?
C1 C2 H2A 119.6 . . ?
C1 C2 C3 120.76(18) . . ?
C3 C2 H2A 119.6 . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.3(2) . . ?
C3 C4 H4 119.8 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.32(18) . . ?
C4 C3 H3 120.3 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C9 H9 119.2 . . ?
C8 C9 C10 121.68(18) . . ?
C8 C9 H9 119.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C13 C12 C7 30.9(2) . . . . ?
O1 C13 C12 C11 -144.80(17) . . . . ?
N2 C13 C12 C7 -149.74(16) . . . . ?
N2 C13 C12 C11 34.6(2) . . . . ?
N2 C14 C17 O3 39.73(18) . . . . ?
N2 C14 C17 O2 -145.16(16) . . . . ?
N1 C7 C8 C9 178.70(17) . . . . ?
N1 C6 C5 C4 177.24(18) . . . . ?
N1 C6 C1 C2 -177.37(18) . . . . ?
C13 N2 C14 C17 51.8(2) . . . . ?
C13 N2 C14 C16 -69.9(2) . . . . ?
C13 N2 C14 C15 169.49(15) . . . . ?
C13 C12 C7 N1 4.5(2) . . . . ?
C13 C12 C7 C8 -174.22(16) . . . . ?
C13 C12 C11 C10 176.43(16) . . . . ?
C12 C7 C8 C9 -2.6(3) . . . . ?
C12 C11 C10 C9 -1.7(3) . . . . ?
C14 N2 C13 O1 0.1(2) . . . . ?
C14 N2 C13 C12 -179.34(14) . . . . ?
C7 N1 C6 C5 158.70(18) . . . . ?
C7 N1 C6 C1 -25.1(3) . . . . ?
C7 C12 C11 C10 0.7(3) . . . . ?
C7 C8 C9 C10 1.6(3) . . . . ?
C6 N1 C7 C12 164.89(17) . . . . ?
C6 N1 C7 C8 -16.4(3) . . . . ?
C6 C5 C4 C3 0.1(3) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C11 C12 C7 N1 -179.82(16) . . . . ?
C11 C12 C7 C8 1.4(2) . . . . ?
C11 C10 C9 C8 0.6(3) . . . . ?
C5 C6 C1 C2 -1.3(3) . . . . ?
C5 C4 C3 C2 -0.6(3) . . . . ?
C1 C6 C5 C4 0.9(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C16 C14 C17 O3 162.34(14) . . . . ?
C16 C14 C17 O2 -22.5(2) . . . . ?
C15 C14 C17 O3 -77.91(18) . . . . ?
C15 C14 C17 O2 97.2(2) . . . . ?
C18 O3 C17 O2 2.7(2) . . . . ?
C18 O3 C17 C14 177.82(14) . . . . ?

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