# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_NIMC2
_database_code_depnum_ccdc_archive 'CCDC 2053600'
loop_
_audit_author_name
_audit_author_address
'Rohit Bhowal Deepak Chopra'
;IISER Bhopal
India
;
_audit_update_record             
;
2021-01-03 deposited with the CCDC.	2021-06-14 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         ?
_chemical_formula_sum            'C22 H27 N3 O3'
_chemical_formula_weight         381.46

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.9422(9)
_cell_length_b                   18.635(2)
_cell_length_c                   29.823(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3858.1(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1316
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      21.13

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5993
_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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25633
_diffrn_reflns_av_unetI/netI     0.1145
_diffrn_reflns_av_R_equivalents  0.1285
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.186
_diffrn_reflns_theta_max         26.661
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3983
_reflns_number_gt                2337
_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)+(0.0852P)²+0.1476P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3983
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1247
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.1931
_refine_ls_wR_factor_gt          0.1574
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.1509(3) 0.27448(10) 0.11400(7) 0.0360(5) Uani 1 1 d . . . . .
O2 O 0.1000(3) 0.49769(10) 0.17384(7) 0.0367(5) Uani 1 1 d . . . . .
O3 O -0.0196(3) 0.16925(11) 0.48842(6) 0.0366(5) Uani 1 1 d . . . . .
N1 N 0.1261(3) 0.38596(12) 0.14419(7) 0.0280(6) Uani 1 1 d . . . . .
N2 N 0.2453(4) 0.19575(13) 0.32136(8) 0.0309(6) Uani 1 1 d . . . . .
C12 C 0.2305(4) 0.22395(14) 0.27948(9) 0.0264(6) Uani 1 1 d . . . . .
N3 N 0.2120(3) 0.15577(13) 0.40963(7) 0.0298(6) Uani 1 1 d . . . . .
C9 C 0.1906(4) 0.28352(14) 0.19264(9) 0.0257(6) Uani 1 1 d . . . . .
C8 C 0.1726(4) 0.32806(15) 0.23076(9) 0.0255(6) Uani 1 1 d . . . . .
C13 C 0.1912(4) 0.29925(15) 0.27492(9) 0.0269(6) Uani 1 1 d . . . . .
C7 C 0.1364(4) 0.40234(15) 0.22552(9) 0.0270(6) Uani 1 1 d . . . . .
C11 C 0.2538(4) 0.18217(16) 0.24138(9) 0.0272(6) Uani 1 1 d . . . . .
C16 C 0.1167(4) 0.44612(16) 0.26251(10) 0.0303(7) Uani 1 1 d . . . . .
C10 C 0.2332(4) 0.21154(15) 0.19873(10) 0.0283(7) Uani 1 1 d . . . . .
C5 C 0.1570(4) 0.31172(15) 0.14782(9) 0.0286(7) Uani 1 1 d . . . . .
C14 C 0.1714(4) 0.34647(16) 0.31139(10) 0.0289(7) Uani 1 1 d . . . . .
C6 C 0.1207(4) 0.43330(15) 0.18038(9) 0.0292(7) Uani 1 1 d . . . . .
C15 C 0.1341(4) 0.41793(16) 0.30558(10) 0.0311(7) Uani 1 1 d . . . . .
C4 C 0.0888(5) 0.41608(17) 0.09917(10) 0.0324(7) Uani 1 1 d . . . . .
C17 C 0.2943(5) 0.12219(16) 0.33185(10) 0.0312(7) Uani 1 1 d . . . . .
C19 C 0.0439(5) 0.11023(16) 0.41752(11) 0.0337(7) Uani 1 1 d . . . . .
C18 C 0.3549(5) 0.12062(17) 0.38075(10) 0.0324(7) Uani 1 1 d . . . . .
C20 C -0.1022(5) 0.14889(19) 0.44637(10) 0.0359(7) Uani 1 1 d . . . . .
C22 C 0.2956(5) 0.17721(18) 0.45267(10) 0.0337(7) Uani 1 1 d . . . . .
C21 C 0.1435(5) 0.21468(17) 0.48092(11) 0.0360(8) Uani 1 1 d . . . . .
C3 C 0.2686(5) 0.44861(18) 0.07773(12) 0.0362(8) Uani 1 1 d . . . . .
C2 C 0.4318(5) 0.39550(17) 0.07019(11) 0.0359(7) Uani 1 1 d . . . . .
C1 C 0.6029(5) 0.4274(2) 0.04560(13) 0.0427(8) Uani 1 1 d . . . . .
H16 H 0.094(4) 0.4983(15) 0.2559(9) 0.026(7) Uiso 1 1 d . . . . .
H10 H 0.245(4) 0.1817(14) 0.1722(8) 0.013(6) Uiso 1 1 d . . . . .
H18A H 0.473(5) 0.1477(15) 0.3839(9) 0.030(8) Uiso 1 1 d . . . . .
H19A H -0.019(4) 0.0949(15) 0.3882(10) 0.032(8) Uiso 1 1 d . . . . .
H17A H 0.179(5) 0.0903(17) 0.3311(10) 0.040(9) Uiso 1 1 d . . . . .
H3A H 0.227(4) 0.4663(16) 0.0477(10) 0.037(8) Uiso 1 1 d . . . . .
H17B H 0.405(4) 0.1066(14) 0.3131(9) 0.025(7) Uiso 1 1 d . . . . .
H2A H 0.472(5) 0.3729(16) 0.1007(10) 0.044(9) Uiso 1 1 d . . . . .
H22A H 0.342(4) 0.1316(16) 0.4695(9) 0.031(8) Uiso 1 1 d . . . . .
H15 H 0.117(4) 0.4474(16) 0.3328(10) 0.033(8) Uiso 1 1 d . . . . .
H4A H 0.041(4) 0.3755(15) 0.0811(8) 0.023(7) Uiso 1 1 d . . . . .
H20A H -0.214(5) 0.1179(16) 0.4537(9) 0.031(8) Uiso 1 1 d . . . . .
H2N H 0.225(5) 0.2301(19) 0.3461(11) 0.045(9) Uiso 1 1 d . . . . .
H3B H 0.318(5) 0.4885(19) 0.0956(10) 0.044(9) Uiso 1 1 d . . . . .
H11 H 0.282(5) 0.1334(19) 0.2427(10) 0.045(9) Uiso 1 1 d . . . . .
H14 H 0.186(4) 0.3294(14) 0.3421(10) 0.023(7) Uiso 1 1 d . . . . .
H21A H 0.098(4) 0.2590(16) 0.4648(9) 0.033(8) Uiso 1 1 d . . . . .
H21B H 0.201(4) 0.2275(14) 0.5124(9) 0.021(7) Uiso 1 1 d . . . . .
H4B H -0.015(5) 0.4490(16) 0.1022(9) 0.032(8) Uiso 1 1 d . . . . .
H19B H 0.088(5) 0.0622(17) 0.4336(10) 0.045(9) Uiso 1 1 d . . . . .
H20B H -0.132(5) 0.1951(19) 0.4309(11) 0.050(10) Uiso 1 1 d . . . . .
H1A H 0.701(5) 0.3916(19) 0.0415(10) 0.044(9) Uiso 1 1 d . . . . .
H22B H 0.402(5) 0.2108(17) 0.4463(10) 0.046(9) Uiso 1 1 d . . . . .
H2B H 0.376(5) 0.3503(19) 0.0512(11) 0.053(10) Uiso 1 1 d . . . . .
H18B H 0.372(4) 0.0668(17) 0.3893(9) 0.039(8) Uiso 1 1 d . . . . .
H1B H 0.657(6) 0.471(2) 0.0604(13) 0.071(12) Uiso 1 1 d . . . . .
H1C H 0.560(5) 0.4448(17) 0.0161(12) 0.046(9) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.225(3) . ?
O2 C6 1.224(3) . ?
O3 C20 1.430(4) . ?
O3 C21 1.431(4) . ?
N1 C6 1.394(4) . ?
N1 C5 1.404(3) . ?
N1 C4 1.478(4) . ?
N2 C12 1.359(3) . ?
N2 C17 1.446(4) . ?
N2 H2N 0.99(3) . ?
C12 C11 1.387(4) . ?
C12 C13 1.436(4) . ?
N3 C19 1.462(4) . ?
N3 C22 1.464(4) . ?
N3 C18 1.468(4) . ?
C9 C10 1.386(4) . ?
C9 C8 1.413(4) . ?
C9 C5 1.455(4) . ?
C8 C7 1.415(4) . ?
C8 C13 1.428(4) . ?
C13 C14 1.406(4) . ?
C7 C16 1.379(4) . ?
C7 C6 1.469(4) . ?
C11 C10 1.392(4) . ?
C11 H11 0.93(3) . ?
C16 C15 1.393(4) . ?
C16 H16 1.00(3) . ?
C10 H10 0.97(3) . ?
C14 C15 1.368(4) . ?
C14 H14 0.98(3) . ?
C15 H15 0.99(3) . ?
C4 C3 1.528(5) . ?
C4 H4A 0.99(3) . ?
C4 H4B 0.95(3) . ?
C17 C18 1.518(4) . ?
C17 H17A 1.00(3) . ?
C17 H17B 1.00(3) . ?
C19 C20 1.513(4) . ?
C19 H19A 1.02(3) . ?
C19 H19B 1.06(3) . ?
C18 H18A 0.97(3) . ?
C18 H18B 1.04(3) . ?
C20 H20A 0.99(3) . ?
C20 H20B 1.00(4) . ?
C22 C21 1.521(5) . ?
C22 H22A 1.04(3) . ?
C22 H22B 0.99(3) . ?
C21 H21A 1.01(3) . ?
C21 H21B 1.05(3) . ?
C3 C2 1.521(4) . ?
C3 H3A 1.00(3) . ?
C3 H3B 0.98(3) . ?
C2 C1 1.517(5) . ?
C2 H2A 1.04(3) . ?
C2 H2B 1.09(4) . ?
C1 H1A 0.96(4) . ?
C1 H1B 1.00(4) . ?
C1 H1C 0.98(3) . ?

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
C20 O3 C21 109.7(2) . . ?
C6 N1 C5 124.6(2) . . ?
C6 N1 C4 117.3(2) . . ?
C5 N1 C4 118.1(2) . . ?
C12 N2 C17 125.7(3) . . ?
C12 N2 H2N 115.2(19) . . ?
C17 N2 H2N 119.1(19) . . ?
N2 C12 C11 121.8(3) . . ?
N2 C12 C13 118.6(2) . . ?
C11 C12 C13 119.6(2) . . ?
C19 N3 C22 109.5(2) . . ?
C19 N3 C18 112.0(2) . . ?
C22 N3 C18 111.6(2) . . ?
C10 C9 C8 118.8(2) . . ?
C10 C9 C5 120.3(3) . . ?
C8 C9 C5 120.8(2) . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 C13 120.9(2) . . ?
C7 C8 C13 119.1(2) . . ?
C14 C13 C8 118.0(3) . . ?
C14 C13 C12 123.8(3) . . ?
C8 C13 C12 118.2(2) . . ?
C16 C7 C8 120.5(2) . . ?
C16 C7 C6 119.6(3) . . ?
C8 C7 C6 119.9(2) . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 122.5(19) . . ?
C10 C11 H11 116.5(19) . . ?
C7 C16 C15 120.4(3) . . ?
C7 C16 H16 115.5(15) . . ?
C15 C16 H16 124.0(15) . . ?
C9 C10 C11 121.5(3) . . ?
C9 C10 H10 117.8(14) . . ?
C11 C10 H10 120.7(14) . . ?
O1 C5 N1 119.3(2) . . ?
O1 C5 C9 123.9(3) . . ?
N1 C5 C9 116.8(2) . . ?
C15 C14 C13 122.0(3) . . ?
C15 C14 H14 117.1(15) . . ?
C13 C14 H14 120.9(15) . . ?
O2 C6 N1 120.0(2) . . ?
O2 C6 C7 122.7(3) . . ?
N1 C6 C7 117.3(2) . . ?
C14 C15 C16 120.0(3) . . ?
C14 C15 H15 117.3(17) . . ?
C16 C15 H15 122.7(17) . . ?
N1 C4 C3 112.8(3) . . ?
N1 C4 H4A 105.3(15) . . ?
C3 C4 H4A 110.7(16) . . ?
N1 C4 H4B 107.0(16) . . ?
C3 C4 H4B 113.8(18) . . ?
H4A C4 H4B 107(2) . . ?
N2 C17 C18 106.9(2) . . ?
N2 C17 H17A 111.9(18) . . ?
C18 C17 H17A 103.4(17) . . ?
N2 C17 H17B 109.6(15) . . ?
C18 C17 H17B 108.7(16) . . ?
H17A C17 H17B 116(2) . . ?
N3 C19 C20 110.5(3) . . ?
N3 C19 H19A 111.6(16) . . ?
C20 C19 H19A 109.5(17) . . ?
N3 C19 H19B 109.3(18) . . ?
C20 C19 H19B 109.9(17) . . ?
H19A C19 H19B 106(2) . . ?
N3 C18 C17 111.6(3) . . ?
N3 C18 H18A 106.5(16) . . ?
C17 C18 H18A 108.5(16) . . ?
N3 C18 H18B 111.4(16) . . ?
C17 C18 H18B 106.5(16) . . ?
H18A C18 H18B 112(2) . . ?
O3 C20 C19 110.9(3) . . ?
O3 C20 H20A 106.0(16) . . ?
C19 C20 H20A 111.9(17) . . ?
O3 C20 H20B 105.1(19) . . ?
C19 C20 H20B 107(2) . . ?
H20A C20 H20B 116(3) . . ?
N3 C22 C21 109.6(3) . . ?
N3 C22 H22A 108.9(15) . . ?
C21 C22 H22A 109.0(16) . . ?
N3 C22 H22B 107.5(18) . . ?
C21 C22 H22B 109.6(18) . . ?
H22A C22 H22B 112(2) . . ?
O3 C21 C22 111.4(2) . . ?
O3 C21 H21A 108.1(17) . . ?
C22 C21 H21A 109.4(16) . . ?
O3 C21 H21B 107.1(15) . . ?
C22 C21 H21B 109.8(15) . . ?
H21A C21 H21B 111(2) . . ?
C2 C3 C4 114.3(3) . . ?
C2 C3 H3A 107.5(18) . . ?
C4 C3 H3A 105.5(18) . . ?
C2 C3 H3B 108(2) . . ?
C4 C3 H3B 111(2) . . ?
H3A C3 H3B 110(3) . . ?
C1 C2 C3 113.6(3) . . ?
C1 C2 H2A 111.8(18) . . ?
C3 C2 H2A 109.5(17) . . ?
C1 C2 H2B 109.4(17) . . ?
C3 C2 H2B 108.4(18) . . ?
H2A C2 H2B 104(2) . . ?
C2 C1 H1A 110(2) . . ?
C2 C1 H1B 114(2) . . ?
H1A C1 H1B 111(3) . . ?
C2 C1 H1C 109(2) . . ?
H1A C1 H1C 109(3) . . ?
H1B C1 H1C 104(3) . . ?

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
C17 N2 C12 C11 2.9(4) . . . . ?
C17 N2 C12 C13 -176.5(3) . . . . ?
C10 C9 C8 C7 177.6(3) . . . . ?
C5 C9 C8 C7 -5.0(4) . . . . ?
C10 C9 C8 C13 -2.2(4) . . . . ?
C5 C9 C8 C13 175.2(2) . . . . ?
C9 C8 C13 C14 -179.9(3) . . . . ?
C7 C8 C13 C14 0.3(4) . . . . ?
C9 C8 C13 C12 0.6(4) . . . . ?
C7 C8 C13 C12 -179.2(3) . . . . ?
N2 C12 C13 C14 1.6(4) . . . . ?
C11 C12 C13 C14 -177.9(3) . . . . ?
N2 C12 C13 C8 -178.9(2) . . . . ?
C11 C12 C13 C8 1.6(4) . . . . ?
C9 C8 C7 C16 179.4(3) . . . . ?
C13 C8 C7 C16 -0.9(4) . . . . ?
C9 C8 C7 C6 -1.0(4) . . . . ?
C13 C8 C7 C6 178.8(2) . . . . ?
N2 C12 C11 C10 178.3(3) . . . . ?
C13 C12 C11 C10 -2.3(4) . . . . ?
C8 C7 C16 C15 0.6(4) . . . . ?
C6 C7 C16 C15 -179.0(3) . . . . ?
C8 C9 C10 C11 1.5(4) . . . . ?
C5 C9 C10 C11 -175.8(3) . . . . ?
C12 C11 C10 C9 0.7(4) . . . . ?
C6 N1 C5 O1 176.9(3) . . . . ?
C4 N1 C5 O1 -0.5(4) . . . . ?
C6 N1 C5 C9 -1.7(4) . . . . ?
C4 N1 C5 C9 -179.2(2) . . . . ?
C10 C9 C5 O1 5.1(4) . . . . ?
C8 C9 C5 O1 -172.2(3) . . . . ?
C10 C9 C5 N1 -176.3(3) . . . . ?
C8 C9 C5 N1 6.4(4) . . . . ?
C8 C13 C14 C15 0.5(4) . . . . ?
C12 C13 C14 C15 179.9(3) . . . . ?
C5 N1 C6 O2 177.3(3) . . . . ?
C4 N1 C6 O2 -5.3(4) . . . . ?
C5 N1 C6 C7 -4.1(4) . . . . ?
C4 N1 C6 C7 173.4(2) . . . . ?
C16 C7 C6 O2 3.7(4) . . . . ?
C8 C7 C6 O2 -175.9(3) . . . . ?
C16 C7 C6 N1 -174.9(2) . . . . ?
C8 C7 C6 N1 5.4(4) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C7 C16 C15 C14 0.2(4) . . . . ?
C6 N1 C4 C3 84.2(3) . . . . ?
C5 N1 C4 C3 -98.2(3) . . . . ?
C12 N2 C17 C18 162.6(3) . . . . ?
C22 N3 C19 C20 57.1(3) . . . . ?
C18 N3 C19 C20 -178.5(3) . . . . ?
C19 N3 C18 C17 77.0(3) . . . . ?
C22 N3 C18 C17 -159.8(3) . . . . ?
N2 C17 C18 N3 50.8(3) . . . . ?
C21 O3 C20 C19 58.6(3) . . . . ?
N3 C19 C20 O3 -58.5(3) . . . . ?
C19 N3 C22 C21 -56.6(3) . . . . ?
C18 N3 C22 C21 178.8(3) . . . . ?
C20 O3 C21 C22 -59.0(3) . . . . ?
N3 C22 C21 O3 58.4(3) . . . . ?
N1 C4 C3 C2 61.3(4) . . . . ?
C4 C3 C2 C1 175.5(3) . . . . ?

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.068


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_NIMC5
_database_code_depnum_ccdc_archive 'CCDC 2053603'
loop_
_audit_author_name
_audit_author_address
'Rohit Bhowal Deepak Chopra'
;IISER Bhopal
India
;
_audit_update_record             
;
2021-01-03 deposited with the CCDC.	2021-06-14 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         ?
_chemical_formula_sum            'C25 H33 N3 O3'
_chemical_formula_weight         423.54

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      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   9.5249(5)
_cell_length_b                   9.5481(6)
_cell_length_c                   12.5232(7)
_cell_angle_alpha                90.010(4)
_cell_angle_beta                 96.492(4)
_cell_angle_gamma                105.918(4)
_cell_volume                     1087.64(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2566
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      25.21


_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7052
_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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21833
_diffrn_reflns_av_unetI/netI     0.0883
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.637
_diffrn_reflns_theta_max         29.129
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5806
_reflns_number_gt                3192
_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)+(0.0682P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5806
_refine_ls_number_parameters     412
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1504
_refine_ls_wR_factor_gt          0.1241
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_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
N1 N 0.08473(15) 0.00725(16) 0.19954(12) 0.0188(4) Uani 1 1 d . . . . .
N2 N -0.09752(17) 0.43578(17) -0.15349(12) 0.0212(4) Uani 1 1 d . . . . .
N3 N -0.33438(16) 0.56914(17) -0.66558(12) 0.0227(4) Uani 1 1 d . . . . .
O1 O 0.30055(13) 0.09703(14) 0.12908(11) 0.0253(3) Uani 1 1 d . . . . .
O2 O -0.12439(14) -0.07191(14) 0.27830(10) 0.0267(3) Uani 1 1 d . . . . .
O3 O -0.58039(14) 0.56720(14) -0.82017(10) 0.0273(3) Uani 1 1 d . . . . .
C1 C 0.3260(3) -0.0880(3) 0.56039(17) 0.0314(5) Uani 1 1 d . . . . .
C2 C 0.2659(2) -0.1420(2) 0.44555(16) 0.0248(5) Uani 1 1 d . . . . .
C3 C 0.2139(2) -0.0296(2) 0.37847(15) 0.0220(4) Uani 1 1 d . . . . .
C4 C 0.1496(2) -0.0901(2) 0.26663(15) 0.0205(4) Uani 1 1 d . . . . .
C5 C 0.1713(2) 0.09591(19) 0.12846(14) 0.0190(4) Uani 1 1 d . . . . .
C6 C -0.0599(2) 0.0041(2) 0.21055(15) 0.0203(4) Uani 1 1 d . . . . .
C7 C -0.12892(19) 0.09494(19) 0.13845(14) 0.0180(4) Uani 1 1 d . . . . .
C8 C -0.04748(19) 0.18328(19) 0.06380(14) 0.0169(4) Uani 1 1 d . . . . .
C9 C 0.10059(19) 0.18441(19) 0.05749(14) 0.0175(4) Uani 1 1 d . . . . .
C10 C 0.1751(2) 0.2682(2) -0.01894(14) 0.0191(4) Uani 1 1 d . . . . .
C11 C 0.1121(2) 0.3523(2) -0.08836(15) 0.0201(4) Uani 1 1 d . . . . .
C12 C -0.03324(19) 0.35605(19) -0.08393(14) 0.0182(4) Uani 1 1 d . . . . .
C13 C -0.11603(19) 0.26991(19) -0.00532(14) 0.0179(4) Uani 1 1 d . . . . .
C14 C -0.2632(2) 0.2644(2) 0.00484(15) 0.0206(4) Uani 1 1 d . . . . .
C15 C -0.3410(2) 0.1757(2) 0.07717(15) 0.0228(4) Uani 1 1 d . . . . .
C16 C -0.2734(2) 0.0908(2) 0.14429(16) 0.0220(4) Uani 1 1 d . . . . .
C17 C -0.0248(2) 0.5142(2) -0.24063(16) 0.0222(4) Uani 1 1 d . . . . .
C18 C -0.1323(2) 0.5668(2) -0.31775(16) 0.0246(5) Uani 1 1 d . . . . .
C19 C -0.0594(2) 0.6479(2) -0.41028(16) 0.0272(5) Uani 1 1 d . . . . .
C20 C -0.1645(2) 0.6810(2) -0.50236(17) 0.0271(5) Uani 1 1 d . . . . .
C21 C -0.2701(2) 0.5440(2) -0.55778(16) 0.0251(5) Uani 1 1 d . . . . .
C22 C -0.4137(2) 0.6801(2) -0.66278(16) 0.0237(4) Uani 1 1 d . . . . .
C23 C -0.4817(2) 0.7006(2) -0.77411(17) 0.0268(5) Uani 1 1 d . . . . .
C24 C -0.5042(2) 0.4579(2) -0.82368(17) 0.0274(5) Uani 1 1 d . . . . .
C25 C -0.4354(2) 0.4327(2) -0.71303(17) 0.0269(5) Uani 1 1 d . . . . .
H4A H 0.0736(18) -0.1767(18) 0.2703(13) 0.009(4) Uiso 1 1 d . . . . .
H1A H 0.407(2) 0.002(2) 0.5627(14) 0.018(5) Uiso 1 1 d . . . . .
H2A H 0.183(2) -0.234(2) 0.4438(15) 0.026(5) Uiso 1 1 d . . . . .
H3A H 0.1454(19) -0.0005(18) 0.4139(13) 0.012(5) Uiso 1 1 d . . . . .
H10 H 0.273(2) 0.263(2) -0.0237(15) 0.028(5) Uiso 1 1 d . . . . .
H14 H -0.3085(19) 0.3268(19) -0.0431(14) 0.016(5) Uiso 1 1 d . . . . .
H18A H -0.216(2) 0.478(2) -0.3464(14) 0.025(5) Uiso 1 1 d . . . . .
H15 H -0.440(2) 0.170(2) 0.0834(15) 0.031(6) Uiso 1 1 d . . . . .
H18B H -0.177(2) 0.628(2) -0.2772(16) 0.028(6) Uiso 1 1 d . . . . .
H4B H 0.224(2) -0.1073(19) 0.2260(14) 0.020(5) Uiso 1 1 d . . . . .
H25A H -0.376(2) 0.358(2) -0.7215(14) 0.023(5) Uiso 1 1 d . . . . .
H25B H -0.519(2) 0.390(2) -0.6643(16) 0.035(6) Uiso 1 1 d . . . . .
H17A H 0.024(2) 0.449(2) -0.2813(15) 0.026(5) Uiso 1 1 d . . . . .
H3B H 0.295(2) 0.059(2) 0.3727(14) 0.022(5) Uiso 1 1 d . . . . .
H2B H 0.342(2) -0.171(2) 0.4102(14) 0.024(5) Uiso 1 1 d . . . . .
H1B H 0.246(2) -0.062(2) 0.5971(16) 0.032(6) Uiso 1 1 d . . . . .
H11 H 0.1656(19) 0.4039(19) -0.1460(14) 0.019(5) Uiso 1 1 d . . . . .
H17B H 0.063(2) 0.598(2) -0.2117(14) 0.022(5) Uiso 1 1 d . . . . .
H16 H -0.329(2) 0.029(2) 0.1940(16) 0.032(6) Uiso 1 1 d . . . . .
H23A H -0.544(2) 0.776(2) -0.7717(15) 0.033(6) Uiso 1 1 d . . . . .
H19A H 0.002(2) 0.591(2) -0.4387(15) 0.025(5) Uiso 1 1 d . . . . .
H22A H -0.343(2) 0.775(2) -0.6347(14) 0.023(5) Uiso 1 1 d . . . . .
H22B H -0.493(2) 0.649(2) -0.6125(16) 0.031(5) Uiso 1 1 d . . . . .
H23B H -0.401(2) 0.736(2) -0.8253(16) 0.034(6) Uiso 1 1 d . . . . .
H20A H -0.109(2) 0.738(2) -0.5578(16) 0.033(6) Uiso 1 1 d . . . . .
H24A H -0.427(2) 0.486(2) -0.8765(15) 0.029(5) Uiso 1 1 d . . . . .
H21A H -0.358(2) 0.495(2) -0.5123(15) 0.026(5) Uiso 1 1 d . . . . .
H20B H -0.229(2) 0.748(2) -0.4749(16) 0.037(6) Uiso 1 1 d . . . . .
H19B H 0.010(2) 0.738(2) -0.3802(16) 0.032(6) Uiso 1 1 d . . . . .
H21B H -0.215(2) 0.464(2) -0.5671(15) 0.029(5) Uiso 1 1 d . . . . .
H24B H -0.579(2) 0.365(2) -0.8533(15) 0.033(6) Uiso 1 1 d . . . . .
H1C H 0.362(2) -0.163(2) 0.6027(18) 0.045(7) Uiso 1 1 d . . . . .
H2N H -0.198(3) 0.436(3) -0.1462(19) 0.062(8) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.392(2) . ?
N1 C5 1.404(2) . ?
N1 C4 1.466(2) . ?
N2 C12 1.360(2) . ?
N2 C17 1.455(2) . ?
N2 H2N 0.97(2) . ?
N3 C22 1.463(2) . ?
N3 C21 1.466(2) . ?
N3 C25 1.469(2) . ?
O1 C5 1.228(2) . ?
O2 C6 1.224(2) . ?
O3 C24 1.428(2) . ?
O3 C23 1.435(2) . ?
C1 C2 1.521(3) . ?
C1 H1A 0.981(19) . ?
C1 H1B 1.02(2) . ?
C1 H1C 1.00(2) . ?
C2 C3 1.517(3) . ?
C2 H2A 1.006(19) . ?
C2 H2B 0.989(18) . ?
C3 C4 1.511(3) . ?
C3 H3A 0.930(17) . ?
C3 H3B 0.991(18) . ?
C4 H4A 0.943(17) . ?
C4 H4B 0.967(18) . ?
C5 C9 1.461(3) . ?
C6 C7 1.476(3) . ?
C7 C16 1.376(2) . ?
C7 C8 1.412(2) . ?
C8 C9 1.419(2) . ?
C8 C13 1.424(2) . ?
C9 C10 1.379(2) . ?
C10 C11 1.381(3) . ?
C10 H10 0.953(19) . ?
C11 C12 1.402(3) . ?
C11 H11 0.985(17) . ?
C12 C13 1.445(2) . ?
C13 C14 1.408(2) . ?
C14 C15 1.377(3) . ?
C14 H14 0.992(18) . ?
C15 C16 1.394(3) . ?
C15 H15 0.94(2) . ?
C16 H16 0.96(2) . ?
C17 C18 1.514(3) . ?
C17 H17A 1.033(19) . ?
C17 H17B 1.017(18) . ?
C18 C19 1.520(3) . ?
C18 H18A 1.019(19) . ?
C18 H18B 0.98(2) . ?
C19 C20 1.530(3) . ?
C19 H19A 1.00(2) . ?
C19 H19B 0.98(2) . ?
C20 C21 1.525(3) . ?
C20 H20A 0.99(2) . ?
C20 H20B 1.08(2) . ?
C21 H21A 1.067(19) . ?
C21 H21B 1.055(19) . ?
C22 C23 1.506(3) . ?
C22 H22A 1.005(18) . ?
C22 H22B 1.02(2) . ?
C23 H23A 1.05(2) . ?
C23 H23B 1.041(19) . ?
C24 C25 1.513(3) . ?
C24 H24A 1.025(19) . ?
C24 H24B 1.01(2) . ?
C25 H25A 1.036(19) . ?
C25 H25B 1.05(2) . ?

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
C6 N1 C5 124.54(15) . . ?
C6 N1 C4 117.19(15) . . ?
C5 N1 C4 118.27(15) . . ?
C12 N2 C17 122.76(16) . . ?
C12 N2 H2N 118.0(14) . . ?
C17 N2 H2N 119.2(14) . . ?
C22 N3 C21 111.46(15) . . ?
C22 N3 C25 109.32(15) . . ?
C21 N3 C25 109.95(15) . . ?
C24 O3 C23 109.94(15) . . ?
C2 C1 H1A 111.8(11) . . ?
C2 C1 H1B 109.4(11) . . ?
H1A C1 H1B 105.9(16) . . ?
C2 C1 H1C 111.6(13) . . ?
H1A C1 H1C 108.7(16) . . ?
H1B C1 H1C 109.3(17) . . ?
C3 C2 C1 113.01(18) . . ?
C3 C2 H2A 109.3(11) . . ?
C1 C2 H2A 111.4(11) . . ?
C3 C2 H2B 109.1(10) . . ?
C1 C2 H2B 109.9(11) . . ?
H2A C2 H2B 103.8(15) . . ?
C4 C3 C2 111.11(17) . . ?
C4 C3 H3A 111.4(11) . . ?
C2 C3 H3A 108.2(10) . . ?
C4 C3 H3B 108.7(10) . . ?
C2 C3 H3B 111.4(10) . . ?
H3A C3 H3B 105.9(15) . . ?
N1 C4 C3 114.54(16) . . ?
N1 C4 H4A 105.9(10) . . ?
C3 C4 H4A 110.2(10) . . ?
N1 C4 H4B 103.9(10) . . ?
C3 C4 H4B 111.5(11) . . ?
H4A C4 H4B 110.5(15) . . ?
O1 C5 N1 119.62(16) . . ?
O1 C5 C9 123.35(16) . . ?
N1 C5 C9 117.03(16) . . ?
O2 C6 N1 119.82(17) . . ?
O2 C6 C7 122.74(17) . . ?
N1 C6 C7 117.44(15) . . ?
C16 C7 C8 120.79(17) . . ?
C16 C7 C6 119.15(16) . . ?
C8 C7 C6 120.06(16) . . ?
C7 C8 C9 120.11(16) . . ?
C7 C8 C13 119.26(16) . . ?
C9 C8 C13 120.63(16) . . ?
C10 C9 C8 118.47(17) . . ?
C10 C9 C5 120.77(16) . . ?
C8 C9 C5 120.74(16) . . ?
C9 C10 C11 122.69(17) . . ?
C9 C10 H10 116.5(12) . . ?
C11 C10 H10 120.8(12) . . ?
C10 C11 C12 120.74(17) . . ?
C10 C11 H11 120.4(10) . . ?
C12 C11 H11 118.6(10) . . ?
N2 C12 C11 121.26(16) . . ?
N2 C12 C13 120.06(16) . . ?
C11 C12 C13 118.66(17) . . ?
C14 C13 C8 118.03(16) . . ?
C14 C13 C12 123.18(17) . . ?
C8 C13 C12 118.78(16) . . ?
C15 C14 C13 121.62(18) . . ?
C15 C14 H14 121.5(10) . . ?
C13 C14 H14 116.9(10) . . ?
C14 C15 C16 120.05(18) . . ?
C14 C15 H15 122.1(12) . . ?
C16 C15 H15 117.9(12) . . ?
C7 C16 C15 120.23(18) . . ?
C7 C16 H16 120.4(12) . . ?
C15 C16 H16 119.3(12) . . ?
N2 C17 C18 110.89(16) . . ?
N2 C17 H17A 110.7(10) . . ?
C18 C17 H17A 110.1(10) . . ?
N2 C17 H17B 111.2(10) . . ?
C18 C17 H17B 111.1(10) . . ?
H17A C17 H17B 102.6(14) . . ?
C17 C18 C19 112.00(17) . . ?
C17 C18 H18A 108.1(10) . . ?
C19 C18 H18A 110.2(10) . . ?
C17 C18 H18B 108.5(11) . . ?
C19 C18 H18B 111.6(11) . . ?
H18A C18 H18B 106.1(15) . . ?
C18 C19 C20 115.41(18) . . ?
C18 C19 H19A 108.5(11) . . ?
C20 C19 H19A 109.7(11) . . ?
C18 C19 H19B 107.4(12) . . ?
C20 C19 H19B 110.3(12) . . ?
H19A C19 H19B 105.1(16) . . ?
C21 C20 C19 113.03(17) . . ?
C21 C20 H20A 107.7(12) . . ?
C19 C20 H20A 110.8(12) . . ?
C21 C20 H20B 108.2(11) . . ?
C19 C20 H20B 111.5(11) . . ?
H20A C20 H20B 105.3(15) . . ?
N3 C21 C20 113.29(16) . . ?
N3 C21 H21A 107.8(10) . . ?
C20 C21 H21A 112.7(10) . . ?
N3 C21 H21B 106.6(10) . . ?
C20 C21 H21B 110.3(10) . . ?
H21A C21 H21B 105.8(14) . . ?
N3 C22 C23 110.18(16) . . ?
N3 C22 H22A 109.2(10) . . ?
C23 C22 H22A 109.0(10) . . ?
N3 C22 H22B 109.2(11) . . ?
C23 C22 H22B 110.3(11) . . ?
H22A C22 H22B 109.0(15) . . ?
O3 C23 C22 111.68(16) . . ?
O3 C23 H23A 106.7(11) . . ?
C22 C23 H23A 110.3(11) . . ?
O3 C23 H23B 107.5(11) . . ?
C22 C23 H23B 110.9(11) . . ?
H23A C23 H23B 109.7(15) . . ?
O3 C24 C25 111.48(17) . . ?
O3 C24 H24A 109.8(11) . . ?
C25 C24 H24A 111.5(11) . . ?
O3 C24 H24B 107.4(11) . . ?
C25 C24 H24B 109.5(11) . . ?
H24A C24 H24B 107.1(15) . . ?
N3 C25 C24 110.38(16) . . ?
N3 C25 H25A 108.5(10) . . ?
C24 C25 H25A 107.9(10) . . ?
N3 C25 H25B 111.0(11) . . ?
C24 C25 H25B 109.3(11) . . ?
H25A C25 H25B 109.8(14) . . ?

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
C1 C2 C3 C4 -177.71(17) . . . . ?
C6 N1 C4 C3 -84.5(2) . . . . ?
C5 N1 C4 C3 96.0(2) . . . . ?
C2 C3 C4 N1 174.82(16) . . . . ?
C6 N1 C5 O1 175.81(16) . . . . ?
C4 N1 C5 O1 -4.7(2) . . . . ?
C6 N1 C5 C9 -3.5(3) . . . . ?
C4 N1 C5 C9 175.95(15) . . . . ?
C5 N1 C6 O2 -176.62(16) . . . . ?
C4 N1 C6 O2 3.9(3) . . . . ?
C5 N1 C6 C7 3.2(3) . . . . ?
C4 N1 C6 C7 -176.24(16) . . . . ?
O2 C6 C7 C16 -2.4(3) . . . . ?
N1 C6 C7 C16 177.72(16) . . . . ?
O2 C6 C7 C8 178.33(17) . . . . ?
N1 C6 C7 C8 -1.5(3) . . . . ?
C16 C7 C8 C9 -178.90(17) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C16 C7 C8 C13 0.6(3) . . . . ?
C6 C7 C8 C13 179.83(16) . . . . ?
C7 C8 C9 C10 177.80(16) . . . . ?
C13 C8 C9 C10 -1.7(3) . . . . ?
C7 C8 C9 C5 -0.6(3) . . . . ?
C13 C8 C9 C5 179.86(16) . . . . ?
O1 C5 C9 C10 4.4(3) . . . . ?
N1 C5 C9 C10 -176.29(15) . . . . ?
O1 C5 C9 C8 -177.19(17) . . . . ?
N1 C5 C9 C8 2.1(3) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
C5 C9 C10 C11 179.34(17) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C17 N2 C12 C11 4.0(3) . . . . ?
C17 N2 C12 C13 -174.31(16) . . . . ?
C10 C11 C12 N2 -178.46(17) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C7 C8 C13 C14 0.6(3) . . . . ?
C9 C8 C13 C14 -179.89(16) . . . . ?
C7 C8 C13 C12 -177.90(15) . . . . ?
C9 C8 C13 C12 1.6(3) . . . . ?
N2 C12 C13 C14 -0.7(3) . . . . ?
C11 C12 C13 C14 -179.11(17) . . . . ?
N2 C12 C13 C8 177.68(16) . . . . ?
C11 C12 C13 C8 -0.7(3) . . . . ?
C8 C13 C14 C15 -1.6(3) . . . . ?
C12 C13 C14 C15 176.82(17) . . . . ?
C13 C14 C15 C16 1.4(3) . . . . ?
C8 C7 C16 C15 -0.9(3) . . . . ?
C6 C7 C16 C15 179.91(17) . . . . ?
C14 C15 C16 C7 -0.1(3) . . . . ?
C12 N2 C17 C18 168.39(17) . . . . ?
N2 C17 C18 C19 -179.45(17) . . . . ?
C17 C18 C19 C20 169.47(18) . . . . ?
C18 C19 C20 C21 -61.8(3) . . . . ?
C22 N3 C21 C20 -58.1(2) . . . . ?
C25 N3 C21 C20 -179.54(17) . . . . ?
C19 C20 C21 N3 -160.20(17) . . . . ?
C21 N3 C22 C23 -178.50(15) . . . . ?
C25 N3 C22 C23 -56.7(2) . . . . ?
C24 O3 C23 C22 -58.0(2) . . . . ?
N3 C22 C23 O3 58.3(2) . . . . ?
C23 O3 C24 C25 57.4(2) . . . . ?
C22 N3 C25 C24 56.5(2) . . . . ?
C21 N3 C25 C24 179.12(16) . . . . ?
O3 C24 C25 N3 -57.5(2) . . . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.062


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_NIMC10
_database_code_depnum_ccdc_archive 'CCDC 2053604'
loop_
_audit_author_name
_audit_author_address
'Rohit Bhowal Deepak Chopra'
;IISER Bhopal
India
;
_audit_update_record             
;
2021-01-03 deposited with the CCDC.	2021-06-14 downloaded from the CCDC.
;
_audit_creation_date             2020-08-29
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H43 N3 O3, C3 H7 N O'
_chemical_formula_sum            'C33 H50 N4 O4'
_chemical_formula_weight         566.77
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.9200(4)
_cell_length_b                   16.6625(17)
_cell_length_c                   18.9799(17)
_cell_angle_alpha                87.245(3)
_cell_angle_beta                 87.143(3)
_cell_angle_gamma                86.580(3)
_cell_volume                     1549.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9655
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      29.65
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1759 before and 0.0769 after correction.
The Ratio of minimum to maximum transmission is 0.8972.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1391
_diffrn_reflns_av_unetI/netI     0.1306
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            47475
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.575
_diffrn_reflns_theta_min         2.427
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4527
_reflns_number_total             8557
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     570
_refine_ls_number_reflns         8557
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1653
_refine_ls_R_factor_gt           0.0679
_refine_ls_restrained_S_all      1.016
_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)+(0.0487P)²+0.4101P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1405
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 1.6402(3) 0.74557(8) 0.78830(7) 0.0229(3) Uani 1 1 d . . . . .
O4 O 1.1327(3) 0.78497(9) 0.34725(7) 0.0265(4) Uani 1 1 d . . . . .
O2 O 2.0246(3) 0.94986(8) 0.66000(7) 0.0254(3) Uani 1 1 d . . . . .
O3 O -0.5433(3) 0.22511(10) -0.07547(7) 0.0317(4) Uani 1 1 d . . . . .
N2 N 1.0678(3) 0.71150(10) 0.49722(9) 0.0174(4) Uani 1 1 d . . . . .
N1 N 1.8403(3) 0.84546(9) 0.72268(8) 0.0168(4) Uani 1 1 d . . . . .
N3 N -0.2514(3) 0.32381(10) 0.01075(8) 0.0190(4) Uani 1 1 d . . . . .
N4 N 0.8184(3) 0.83725(10) 0.27209(9) 0.0250(4) Uani 1 1 d . . . . .
C12 C 1.2094(3) 0.72942(11) 0.55307(10) 0.0142(4) Uani 1 1 d . . . . .
C8 C 1.5420(3) 0.81093(11) 0.60589(10) 0.0134(4) Uani 1 1 d . . . . .
C7 C 1.7222(3) 0.87425(11) 0.60021(10) 0.0151(4) Uani 1 1 d . . . . .
C9 C 1.5101(3) 0.76545(11) 0.67014(10) 0.0144(4) Uani 1 1 d . . . . .
C13 C 1.3944(3) 0.79415(11) 0.54634(10) 0.0142(4) Uani 1 1 d . . . . .
C17 C 0.8839(4) 0.64588(12) 0.49777(10) 0.0173(4) Uani 1 1 d . . . . .
C5 C 1.6613(4) 0.78242(11) 0.73086(10) 0.0171(4) Uani 1 1 d . . . . .
C11 C 1.1816(4) 0.68676(12) 0.61770(10) 0.0169(4) Uani 1 1 d . . . . .
C14 C 1.4352(4) 0.84139(12) 0.48341(10) 0.0173(4) Uani 1 1 d . . . . .
C10 C 1.3285(4) 0.70507(12) 0.67477(11) 0.0159(4) Uani 1 1 d . . . . .
C15 C 1.6129(4) 0.90224(12) 0.47941(11) 0.0187(4) Uani 1 1 d . . . . .
C6 C 1.8743(4) 0.89371(12) 0.66159(10) 0.0177(4) Uani 1 1 d . . . . .
C18 C 0.7626(4) 0.64448(12) 0.42609(10) 0.0178(4) Uani 1 1 d . . . . .
C31 C 0.9950(4) 0.84237(14) 0.32211(11) 0.0224(5) Uani 1 1 d . . . . .
C23 C 0.0520(4) 0.45267(12) 0.22491(10) 0.0179(4) Uani 1 1 d . . . . .
C20 C 0.4802(4) 0.57871(12) 0.34206(10) 0.0180(4) Uani 1 1 d . . . . .
C16 C 1.7555(4) 0.91872(12) 0.53815(10) 0.0184(4) Uani 1 1 d . . . . .
C19 C 0.5831(4) 0.57459(12) 0.41643(11) 0.0184(4) Uani 1 1 d . . . . .
C22 C 0.2225(4) 0.51968(13) 0.24742(11) 0.0191(4) Uani 1 1 d . . . . .
C25 C -0.1550(4) 0.38961(13) 0.12147(10) 0.0191(4) Uani 1 1 d . . . . .
C4 C 1.9854(4) 0.86568(13) 0.78456(11) 0.0203(5) Uani 1 1 d . . . . .
C21 C 0.3043(4) 0.51121(12) 0.32369(11) 0.0179(4) Uani 1 1 d . . . . .
C26 C -0.2059(4) 0.39953(13) 0.04309(11) 0.0221(5) Uani 1 1 d . . . . .
C24 C -0.0168(4) 0.46147(13) 0.14742(11) 0.0202(5) Uani 1 1 d . . . . .
C3 C 1.8220(4) 0.92949(15) 0.82543(12) 0.0261(5) Uani 1 1 d . . . . .
C27 C -0.5139(4) 0.29283(14) 0.03461(12) 0.0237(5) Uani 1 1 d . . . . .
C29 C -0.2863(4) 0.25545(15) -0.09827(12) 0.0304(6) Uani 1 1 d . . . . .
C30 C -0.2445(5) 0.33447(14) -0.06612(11) 0.0268(5) Uani 1 1 d . . . . .
C28 C -0.5569(5) 0.21556(15) -0.00002(11) 0.0298(5) Uani 1 1 d . . . . .
C33 C 0.7585(5) 0.76043(15) 0.24547(13) 0.0302(5) Uani 1 1 d . . . . .
C2 C 1.9659(5) 0.95731(15) 0.88792(13) 0.0313(6) Uani 1 1 d . . . . .
C32 C 0.6561(5) 0.90789(17) 0.24721(18) 0.0450(7) Uani 1 1 d . . . . .
C1 C 1.8119(10) 1.0286(3) 0.9206(2) 0.0811(14) Uani 1 1 d . . . . .
H20A H 0.375(3) 0.6314(12) 0.3332(9) 0.012(5) Uiso 1 1 d . . . . .
H25A H -0.034(4) 0.3409(12) 0.1293(10) 0.018(5) Uiso 1 1 d . . . . .
H24A H -0.135(4) 0.5122(12) 0.1378(10) 0.022(5) Uiso 1 1 d . . . . .
H18A H 0.654(4) 0.6952(12) 0.4178(10) 0.020(5) Uiso 1 1 d . . . . .
H30A H -0.068(4) 0.3540(12) -0.0828(10) 0.024(5) Uiso 1 1 d . . . . .
H4A H 2.017(4) 0.8163(13) 0.8144(11) 0.027(6) Uiso 1 1 d . . . . .
H19A H 0.429(4) 0.5765(11) 0.4523(10) 0.015(5) Uiso 1 1 d . . . . .
H16 H 1.876(4) 0.9630(12) 0.5357(10) 0.018(5) Uiso 1 1 d . . . . .
H23A H 0.150(4) 0.4011(13) 0.2344(10) 0.024(6) Uiso 1 1 d . . . . .
H25B H -0.326(4) 0.3821(11) 0.1489(10) 0.019(5) Uiso 1 1 d . . . . .
H21A H 0.137(4) 0.5110(11) 0.3561(9) 0.013(5) Uiso 1 1 d . . . . .
H22A H 0.116(4) 0.5728(13) 0.2382(10) 0.030(6) Uiso 1 1 d . . . . .
H17A H 0.740(4) 0.6531(11) 0.5348(10) 0.022(5) Uiso 1 1 d . . . . .
H3A H 1.651(4) 0.9088(13) 0.8432(11) 0.034(6) Uiso 1 1 d . . . . .
H33A H 0.758(4) 0.7644(13) 0.1927(13) 0.039(6) Uiso 1 1 d . . . . .
H27A H -0.667(4) 0.3325(13) 0.0222(11) 0.033(6) Uiso 1 1 d . . . . .
H19B H 0.682(4) 0.5223(13) 0.4258(10) 0.021(5) Uiso 1 1 d . . . . .
H21B H 0.403(4) 0.4583(14) 0.3333(11) 0.035(6) Uiso 1 1 d . . . . .
H17B H 0.990(3) 0.5923(12) 0.5094(9) 0.014(5) Uiso 1 1 d . . . . .
H4B H 2.167(4) 0.8862(12) 0.7655(10) 0.023(5) Uiso 1 1 d . . . . .
H28A H -0.418(4) 0.1712(13) 0.0158(11) 0.029(6) Uiso 1 1 d . . . . .
H3B H 1.785(4) 0.9768(14) 0.7917(12) 0.033(6) Uiso 1 1 d . . . . .
H24B H 0.151(4) 0.4693(11) 0.1183(10) 0.020(5) Uiso 1 1 d . . . . .
H18B H 0.909(4) 0.6434(11) 0.3896(10) 0.021(5) Uiso 1 1 d . . . . .
H20B H 0.642(4) 0.5796(12) 0.3083(10) 0.023(5) Uiso 1 1 d . . . . .
H31 H 1.012(4) 0.9005(13) 0.3356(10) 0.025(5) Uiso 1 1 d . . . . .
H33B H 0.900(5) 0.7185(15) 0.2616(12) 0.041(7) Uiso 1 1 d . . . . .
H11 H 1.057(4) 0.6450(12) 0.6226(10) 0.018(5) Uiso 1 1 d . . . . .
H15 H 1.636(4) 0.9342(12) 0.4372(11) 0.019(5) Uiso 1 1 d . . . . .
H2A H 1.986(4) 0.9108(15) 0.9233(12) 0.040(7) Uiso 1 1 d . . . . .
H26A H -0.048(4) 0.4215(12) 0.0189(10) 0.022(5) Uiso 1 1 d . . . . .
H33C H 0.572(5) 0.7474(13) 0.2636(12) 0.041(7) Uiso 1 1 d . . . . .
H22B H 0.393(4) 0.5203(12) 0.2168(10) 0.022(5) Uiso 1 1 d . . . . .
H14 H 1.338(4) 0.8295(11) 0.4411(10) 0.018(5) Uiso 1 1 d . . . . .
H23B H -0.119(4) 0.4524(12) 0.2549(11) 0.029(6) Uiso 1 1 d . . . . .
H27B H -0.521(4) 0.2841(12) 0.0878(12) 0.029(6) Uiso 1 1 d . . . . .
H28B H -0.741(5) 0.1985(13) 0.0125(11) 0.035(6) Uiso 1 1 d . . . . .
H26B H -0.363(4) 0.4382(13) 0.0368(10) 0.028(6) Uiso 1 1 d . . . . .
H30B H -0.394(4) 0.3773(13) -0.0811(11) 0.029(6) Uiso 1 1 d . . . . .
H2B H 2.155(5) 0.9688(13) 0.8733(11) 0.036(6) Uiso 1 1 d . . . . .
H10 H 1.305(4) 0.6763(12) 0.7193(11) 0.021(5) Uiso 1 1 d . . . . .
H29A H -0.291(4) 0.2644(13) -0.1520(12) 0.035(6) Uiso 1 1 d . . . . .
H29B H -0.126(5) 0.2121(14) -0.0847(12) 0.040(7) Uiso 1 1 d . . . . .
H32A H 0.674(5) 0.9102(15) 0.1951(14) 0.052(8) Uiso 1 1 d . . . . .
H32B H 0.462(6) 0.9049(16) 0.2603(13) 0.060(8) Uiso 1 1 d . . . . .
H32C H 0.723(6) 0.961(2) 0.2680(16) 0.086(10) Uiso 1 1 d . . . . .
H2 H 1.093(4) 0.7354(13) 0.4569(12) 0.029(7) Uiso 1 1 d . . . . .
H1A H 1.914(5) 1.0468(17) 0.9587(16) 0.068(9) Uiso 1 1 d . . . . .
H1B H 1.632(8) 1.016(3) 0.938(2) 0.126(19) Uiso 1 1 d . . . . .
H1C H 1.780(7) 1.074(2) 0.8858(18) 0.093(12) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.228(2) . ?
O4 C31 1.230(2) . ?
O2 C6 1.225(2) . ?
O3 C29 1.429(2) . ?
O3 C28 1.432(3) . ?
N2 C12 1.352(2) . ?
N2 C17 1.460(2) . ?
N2 H2 0.85(2) . ?
N1 C5 1.409(2) . ?
N1 C6 1.388(2) . ?
N1 C4 1.467(2) . ?
N3 C26 1.463(3) . ?
N3 C27 1.462(2) . ?
N3 C30 1.460(3) . ?
N4 C31 1.328(3) . ?
N4 C33 1.450(3) . ?
N4 C32 1.455(3) . ?
C12 C13 1.449(2) . ?
C12 C11 1.393(3) . ?
C8 C7 1.415(2) . ?
C8 C9 1.411(3) . ?
C8 C13 1.421(3) . ?
C7 C6 1.475(3) . ?
C7 C16 1.369(3) . ?
C9 C5 1.450(3) . ?
C9 C10 1.382(3) . ?
C13 C14 1.411(3) . ?
C17 C18 1.514(3) . ?
C17 H17A 0.978(19) . ?
C17 H17B 1.027(19) . ?
C11 C10 1.387(3) . ?
C11 H11 0.954(19) . ?
C14 C15 1.375(3) . ?
C14 H14 0.990(19) . ?
C10 H10 0.96(2) . ?
C15 C16 1.393(3) . ?
C15 H15 0.95(2) . ?
C18 C19 1.526(3) . ?
C18 H18A 0.98(2) . ?
C18 H18B 0.975(19) . ?
C31 H31 1.02(2) . ?
C23 C22 1.525(3) . ?
C23 C24 1.524(3) . ?
C23 H23A 0.97(2) . ?
C23 H23B 0.99(2) . ?
C20 C19 1.520(3) . ?
C20 C21 1.523(3) . ?
C20 H20A 1.003(19) . ?
C20 H20B 0.998(19) . ?
C16 H16 0.972(19) . ?
C19 H19A 0.995(18) . ?
C19 H19B 0.99(2) . ?
C22 C21 1.520(3) . ?
C22 H22A 1.02(2) . ?
C22 H22B 0.995(19) . ?
C25 C26 1.520(3) . ?
C25 C24 1.525(3) . ?
C25 H25A 0.99(2) . ?
C25 H25B 0.980(19) . ?
C4 C3 1.514(3) . ?
C4 H4A 0.99(2) . ?
C4 H4B 1.02(2) . ?
C21 H21A 1.002(17) . ?
C21 H21B 0.99(2) . ?
C26 H26A 0.96(2) . ?
C26 H26B 0.98(2) . ?
C24 H24A 1.01(2) . ?
C24 H24B 0.983(19) . ?
C3 C2 1.516(3) . ?
C3 H3A 0.97(2) . ?
C3 H3B 1.01(2) . ?
C27 C28 1.504(3) . ?
C27 H27A 1.00(2) . ?
C27 H27B 1.01(2) . ?
C29 C30 1.507(3) . ?
C29 H29A 1.03(2) . ?
C29 H29B 1.07(2) . ?
C30 H30A 0.98(2) . ?
C30 H30B 1.03(2) . ?
C28 H28A 1.02(2) . ?
C28 H28B 0.98(2) . ?
C33 H33A 1.00(2) . ?
C33 H33B 1.00(2) . ?
C33 H33C 0.99(2) . ?
C2 C1 1.512(4) . ?
C2 H2A 1.00(2) . ?
C2 H2B 0.98(2) . ?
C32 H32A 0.99(3) . ?
C32 H32B 0.98(3) . ?
C32 H32C 1.06(3) . ?
C1 H1A 0.97(3) . ?
C1 H1B 0.96(4) . ?
C1 H1C 0.99(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C29 O3 C28 109.07(16) . . ?
C12 N2 C17 124.25(18) . . ?
C12 N2 H2 121.4(15) . . ?
C17 N2 H2 114.1(14) . . ?
C5 N1 C4 117.85(17) . . ?
C6 N1 C5 124.52(16) . . ?
C6 N1 C4 117.46(16) . . ?
C27 N3 C26 111.63(15) . . ?
C30 N3 C26 110.76(16) . . ?
C30 N3 C27 108.48(15) . . ?
C31 N4 C33 121.61(19) . . ?
C31 N4 C32 120.9(2) . . ?
C33 N4 C32 117.2(2) . . ?
N2 C12 C13 119.96(17) . . ?
N2 C12 C11 121.29(17) . . ?
C11 C12 C13 118.75(17) . . ?
C7 C8 C13 119.15(17) . . ?
C9 C8 C7 120.03(17) . . ?
C9 C8 C13 120.82(16) . . ?
C8 C7 C6 120.18(17) . . ?
C16 C7 C8 120.62(17) . . ?
C16 C7 C6 119.20(17) . . ?
C8 C9 C5 120.83(17) . . ?
C10 C9 C8 118.90(17) . . ?
C10 C9 C5 120.26(18) . . ?
C8 C13 C12 118.53(17) . . ?
C14 C13 C12 123.13(17) . . ?
C14 C13 C8 118.35(17) . . ?
N2 C17 C18 109.13(17) . . ?
N2 C17 H17A 109.8(11) . . ?
N2 C17 H17B 109.5(10) . . ?
C18 C17 H17A 110.7(11) . . ?
C18 C17 H17B 110.4(10) . . ?
H17A C17 H17B 107.2(15) . . ?
O1 C5 N1 118.91(17) . . ?
O1 C5 C9 123.84(17) . . ?
N1 C5 C9 117.25(17) . . ?
C12 C11 H11 118.9(12) . . ?
C10 C11 C12 121.09(18) . . ?
C10 C11 H11 120.0(12) . . ?
C13 C14 H14 119.3(11) . . ?
C15 C14 C13 121.15(18) . . ?
C15 C14 H14 119.5(11) . . ?
C9 C10 C11 121.91(19) . . ?
C9 C10 H10 117.6(12) . . ?
C11 C10 H10 120.5(12) . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 120.3(12) . . ?
C16 C15 H15 119.5(12) . . ?
O2 C6 N1 120.36(17) . . ?
O2 C6 C7 122.52(18) . . ?
N1 C6 C7 117.12(16) . . ?
C17 C18 C19 115.31(17) . . ?
C17 C18 H18A 108.4(11) . . ?
C17 C18 H18B 109.2(11) . . ?
C19 C18 H18A 108.6(11) . . ?
C19 C18 H18B 108.7(11) . . ?
H18A C18 H18B 106.3(16) . . ?
O4 C31 N4 124.5(2) . . ?
O4 C31 H31 123.3(11) . . ?
N4 C31 H31 112.1(11) . . ?
C22 C23 H23A 108.9(11) . . ?
C22 C23 H23B 108.7(12) . . ?
C24 C23 C22 113.01(17) . . ?
C24 C23 H23A 110.0(12) . . ?
C24 C23 H23B 109.5(12) . . ?
H23A C23 H23B 106.4(17) . . ?
C19 C20 C21 116.37(17) . . ?
C19 C20 H20A 109.6(10) . . ?
C19 C20 H20B 107.7(11) . . ?
C21 C20 H20A 108.4(10) . . ?
C21 C20 H20B 108.8(11) . . ?
H20A C20 H20B 105.5(15) . . ?
C7 C16 C15 120.54(18) . . ?
C7 C16 H16 119.4(11) . . ?
C15 C16 H16 120.1(11) . . ?
C18 C19 H19A 109.2(10) . . ?
C18 C19 H19B 111.4(11) . . ?
C20 C19 C18 110.25(17) . . ?
C20 C19 H19A 111.1(10) . . ?
C20 C19 H19B 109.8(11) . . ?
H19A C19 H19B 105.0(16) . . ?
C23 C22 H22A 107.7(11) . . ?
C23 C22 H22B 108.6(11) . . ?
C21 C22 C23 114.52(17) . . ?
C21 C22 H22A 110.6(11) . . ?
C21 C22 H22B 107.7(11) . . ?
H22A C22 H22B 107.5(16) . . ?
C26 C25 C24 111.64(17) . . ?
C26 C25 H25A 108.3(11) . . ?
C26 C25 H25B 110.4(11) . . ?
C24 C25 H25A 108.3(11) . . ?
C24 C25 H25B 109.9(11) . . ?
H25A C25 H25B 108.1(16) . . ?
N1 C4 C3 110.49(16) . . ?
N1 C4 H4A 108.6(12) . . ?
N1 C4 H4B 106.0(11) . . ?
C3 C4 H4A 110.8(12) . . ?
C3 C4 H4B 111.0(11) . . ?
H4A C4 H4B 109.9(16) . . ?
C20 C21 H21A 109.5(10) . . ?
C20 C21 H21B 109.5(12) . . ?
C22 C21 C20 111.79(17) . . ?
C22 C21 H21A 109.8(10) . . ?
C22 C21 H21B 110.8(12) . . ?
H21A C21 H21B 105.1(16) . . ?
N3 C26 C25 113.50(17) . . ?
N3 C26 H26A 107.3(11) . . ?
N3 C26 H26B 110.5(12) . . ?
C25 C26 H26A 108.7(11) . . ?
C25 C26 H26B 108.4(12) . . ?
H26A C26 H26B 108.3(17) . . ?
C23 C24 C25 113.77(17) . . ?
C23 C24 H24A 111.0(11) . . ?
C23 C24 H24B 109.2(11) . . ?
C25 C24 H24A 109.2(11) . . ?
C25 C24 H24B 108.7(11) . . ?
H24A C24 H24B 104.5(16) . . ?
C4 C3 C2 113.73(18) . . ?
C4 C3 H3A 109.7(13) . . ?
C4 C3 H3B 107.2(12) . . ?
C2 C3 H3A 107.6(12) . . ?
C2 C3 H3B 109.0(12) . . ?
H3A C3 H3B 109.6(17) . . ?
N3 C27 C28 110.55(17) . . ?
N3 C27 H27A 110.6(12) . . ?
N3 C27 H27B 109.7(11) . . ?
C28 C27 H27A 108.0(12) . . ?
C28 C27 H27B 110.4(12) . . ?
H27A C27 H27B 107.5(16) . . ?
O3 C29 C30 111.50(17) . . ?
O3 C29 H29A 106.1(11) . . ?
O3 C29 H29B 109.6(12) . . ?
C30 C29 H29A 109.0(12) . . ?
C30 C29 H29B 110.2(12) . . ?
H29A C29 H29B 110.4(17) . . ?
N3 C30 C29 109.81(19) . . ?
N3 C30 H30A 109.1(11) . . ?
N3 C30 H30B 109.7(11) . . ?
C29 C30 H30A 109.8(11) . . ?
C29 C30 H30B 110.5(11) . . ?
H30A C30 H30B 107.8(17) . . ?
O3 C28 C27 112.14(19) . . ?
O3 C28 H28A 109.8(12) . . ?
O3 C28 H28B 105.3(12) . . ?
C27 C28 H28A 110.8(11) . . ?
C27 C28 H28B 109.7(13) . . ?
H28A C28 H28B 109.0(18) . . ?
N4 C33 H33A 110.0(13) . . ?
N4 C33 H33B 108.8(13) . . ?
N4 C33 H33C 108.2(13) . . ?
H33A C33 H33B 110.6(18) . . ?
H33A C33 H33C 107.7(17) . . ?
H33B C33 H33C 111.6(19) . . ?
C3 C2 H2A 108.3(13) . . ?
C3 C2 H2B 109.6(12) . . ?
C1 C2 C3 111.4(2) . . ?
C1 C2 H2A 111.0(13) . . ?
C1 C2 H2B 112.2(13) . . ?
H2A C2 H2B 103.9(18) . . ?
N4 C32 H32A 107.4(15) . . ?
N4 C32 H32B 112.7(16) . . ?
N4 C32 H32C 110.8(17) . . ?
H32A C32 H32B 107(2) . . ?
H32A C32 H32C 111(2) . . ?
H32B C32 H32C 108(2) . . ?
C2 C1 H1A 109.4(16) . . ?
C2 C1 H1B 112(3) . . ?
C2 C1 H1C 112(2) . . ?
H1A C1 H1B 110(3) . . ?
H1A C1 H1C 109(3) . . ?
H1B C1 H1C 104(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C29 C30 N3 60.3(2) . . . . ?
N2 C12 C13 C8 -179.42(16) . . . . ?
N2 C12 C13 C14 0.6(3) . . . . ?
N2 C12 C11 C10 179.63(17) . . . . ?
N2 C17 C18 C19 175.18(16) . . . . ?
N1 C4 C3 C2 -176.6(2) . . . . ?
N3 C27 C28 O3 -57.5(3) . . . . ?
C12 N2 C17 C18 179.94(17) . . . . ?
C12 C13 C14 C15 180.00(17) . . . . ?
C12 C11 C10 C9 -0.7(3) . . . . ?
C8 C7 C6 O2 -177.18(17) . . . . ?
C8 C7 C6 N1 2.6(2) . . . . ?
C8 C7 C16 C15 -0.2(3) . . . . ?
C8 C9 C5 O1 179.21(17) . . . . ?
C8 C9 C5 N1 -0.3(2) . . . . ?
C8 C9 C10 C11 1.5(3) . . . . ?
C8 C13 C14 C15 0.0(3) . . . . ?
C7 C8 C9 C5 -0.3(2) . . . . ?
C7 C8 C9 C10 178.62(16) . . . . ?
C7 C8 C13 C12 -179.65(15) . . . . ?
C7 C8 C13 C14 0.4(2) . . . . ?
C9 C8 C7 C6 -0.9(2) . . . . ?
C9 C8 C7 C16 179.88(17) . . . . ?
C9 C8 C13 C12 0.2(2) . . . . ?
C9 C8 C13 C14 -179.78(16) . . . . ?
C13 C12 C11 C10 -0.4(3) . . . . ?
C13 C8 C7 C6 178.99(16) . . . . ?
C13 C8 C7 C16 -0.3(2) . . . . ?
C13 C8 C9 C5 179.82(16) . . . . ?
C13 C8 C9 C10 -1.2(2) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C17 N2 C12 C13 177.83(16) . . . . ?
C17 N2 C12 C11 -2.2(3) . . . . ?
C17 C18 C19 C20 -178.53(16) . . . . ?
C5 N1 C6 O2 176.43(16) . . . . ?
C5 N1 C6 C7 -3.4(2) . . . . ?
C5 N1 C4 C3 -90.5(2) . . . . ?
C5 C9 C10 C11 -179.57(17) . . . . ?
C11 C12 C13 C8 0.6(2) . . . . ?
C11 C12 C13 C14 -179.41(17) . . . . ?
C14 C15 C16 C7 0.5(3) . . . . ?
C10 C9 C5 O1 0.3(3) . . . . ?
C10 C9 C5 N1 -179.19(16) . . . . ?
C6 N1 C5 O1 -177.26(16) . . . . ?
C6 N1 C5 C9 2.2(2) . . . . ?
C6 N1 C4 C3 84.9(2) . . . . ?
C6 C7 C16 C15 -179.45(17) . . . . ?
C23 C22 C21 C20 178.47(16) . . . . ?
C16 C7 C6 O2 2.1(3) . . . . ?
C16 C7 C6 N1 -178.12(16) . . . . ?
C19 C20 C21 C22 -177.76(17) . . . . ?
C22 C23 C24 C25 172.48(17) . . . . ?
C4 N1 C5 O1 -2.2(2) . . . . ?
C4 N1 C5 C9 177.31(16) . . . . ?
C4 N1 C6 O2 1.3(2) . . . . ?
C4 N1 C6 C7 -178.47(15) . . . . ?
C4 C3 C2 C1 172.2(3) . . . . ?
C21 C20 C19 C18 178.25(16) . . . . ?
C26 N3 C27 C28 179.35(18) . . . . ?
C26 N3 C30 C29 178.91(18) . . . . ?
C26 C25 C24 C23 -177.08(17) . . . . ?
C24 C23 C22 C21 -177.79(17) . . . . ?
C24 C25 C26 N3 160.77(16) . . . . ?
C27 N3 C26 C25 70.4(2) . . . . ?
C27 N3 C30 C29 -58.2(2) . . . . ?
C29 O3 C28 C27 56.9(2) . . . . ?
C30 N3 C26 C25 -168.63(17) . . . . ?
C30 N3 C27 C28 57.0(2) . . . . ?
C28 O3 C29 C30 -58.2(3) . . . . ?
C33 N4 C31 O4 4.2(3) . . . . ?
C32 N4 C31 O4 177.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_NIMC3
_database_code_depnum_ccdc_archive 'CCDC 2053601'
loop_
_audit_author_name
_audit_author_address
'Rohit Bhowal Deepak Chopra'
;IISER Bhopal
India
;
_audit_update_record             
;
2021-01-03 deposited with the CCDC.	2021-06-14 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         ?
_chemical_formula_sum            'C23 H29 N3 O3'
_chemical_formula_weight         395.49

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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 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+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   24.1436(7)
_cell_length_b                   9.2164(3)
_cell_length_c                   18.0242(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4010.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5747
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      29.78

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             1696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6820
_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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21769
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.260
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4933
_reflns_number_gt                3972
_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)+(0.0532P)²+1.5952P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4933
_refine_ls_number_parameters     378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1159
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.13150(4) 0.10518(11) 0.20244(5) 0.0215(2) Uani 1 1 d . . . . .
O1 O 0.08565(4) -0.35102(11) 0.27757(6) 0.0251(2) Uani 1 1 d . . . . .
N2 N -0.08501(5) 0.01181(14) 0.47510(6) 0.0184(2) Uani 1 1 d . . . . .
C8 C 0.03004(5) -0.00556(15) 0.33969(7) 0.0143(3) Uani 1 1 d . . . . .
N1 N 0.10925(5) -0.12220(13) 0.24163(6) 0.0176(2) Uani 1 1 d . . . . .
C7 C 0.06299(5) 0.08884(15) 0.29614(7) 0.0151(3) Uani 1 1 d . . . . .
O3 O -0.14757(5) 0.55450(12) 0.46085(7) 0.0329(3) Uani 1 1 d . . . . .
C9 C 0.03667(5) -0.15760(15) 0.33408(7) 0.0167(3) Uani 1 1 d . . . . .
N3 N -0.16253(5) 0.25019(13) 0.48680(6) 0.0179(2) Uani 1 1 d . . . . .
C13 C -0.00996(5) 0.05441(15) 0.38879(7) 0.0150(3) Uani 1 1 d . . . . .
C12 C -0.04488(5) -0.04285(15) 0.43084(7) 0.0163(3) Uani 1 1 d . . . . .
C6 C 0.10358(5) 0.02821(15) 0.24299(7) 0.0162(3) Uani 1 1 d . . . . .
C11 C -0.03633(6) -0.19263(16) 0.42462(8) 0.0191(3) Uani 1 1 d . . . . .
C15 C 0.01892(6) 0.29619(15) 0.35161(8) 0.0191(3) Uani 1 1 d . . . . .
C16 C 0.05757(5) 0.23755(15) 0.30194(7) 0.0170(3) Uani 1 1 d . . . . .
C10 C 0.00362(6) -0.24712(15) 0.37710(8) 0.0196(3) Uani 1 1 d . . . . .
C5 C 0.07748(5) -0.22054(15) 0.28377(7) 0.0180(3) Uani 1 1 d . . . . .
C14 C -0.01405(5) 0.20685(15) 0.39387(7) 0.0173(3) Uani 1 1 d . . . . .
C17 C -0.12436(6) -0.07879(16) 0.51510(8) 0.0196(3) Uani 1 1 d . . . . .
C4 C 0.15058(6) -0.18585(18) 0.19092(8) 0.0213(3) Uani 1 1 d . . . . .
C3 C 0.20407(6) -0.22603(16) 0.23082(8) 0.0213(3) Uani 1 1 d . . . . .
C19 C -0.19657(6) 0.12247(17) 0.50667(8) 0.0225(3) Uani 1 1 d . . . . .
C18 C -0.16601(6) 0.01598(16) 0.55637(8) 0.0211(3) Uani 1 1 d . . . . .
C2 C 0.23796(6) -0.09606(17) 0.25628(8) 0.0222(3) Uani 1 1 d . . . . .
C20 C -0.18590(6) 0.32310(17) 0.42145(8) 0.0231(3) Uani 1 1 d . . . . .
C1 C 0.29017(7) -0.1402(2) 0.29811(10) 0.0297(4) Uani 1 1 d . . . . .
C23 C -0.15949(7) 0.35499(17) 0.54764(9) 0.0248(3) Uani 1 1 d . . . . .
C22 C -0.12524(7) 0.48487(19) 0.52491(9) 0.0299(4) Uani 1 1 d . . . . .
C21 C -0.15098(7) 0.45287(18) 0.40120(9) 0.0290(4) Uani 1 1 d . . . . .
H14 H -0.0436(6) 0.2545(17) 0.4297(8) 0.019(4) Uiso 1 1 d . . . . .
H1A H 0.2806(8) -0.194(2) 0.3469(11) 0.047(6) Uiso 1 1 d . . . . .
H17A H -0.1030(7) -0.1430(17) 0.5519(9) 0.023(4) Uiso 1 1 d . . . . .
H16 H 0.0789(6) 0.3011(18) 0.2716(9) 0.019(4) Uiso 1 1 d . . . . .
H19A H -0.2322(7) 0.1532(18) 0.5321(9) 0.029(4) Uiso 1 1 d . . . . .
H2A H 0.2474(7) -0.0359(18) 0.2119(9) 0.022(4) Uiso 1 1 d . . . . .
H3A H 0.1952(7) -0.2883(19) 0.2729(9) 0.027(4) Uiso 1 1 d . . . . .
H10 H 0.0079(6) -0.3501(18) 0.3727(9) 0.019(4) Uiso 1 1 d . . . . .
H15 H 0.0160(6) 0.3988(18) 0.3552(9) 0.019(4) Uiso 1 1 d . . . . .
H2B H 0.2157(7) -0.0287(18) 0.2881(9) 0.024(4) Uiso 1 1 d . . . . .
H22A H -0.0873(7) 0.4573(17) 0.5141(8) 0.017(4) Uiso 1 1 d . . . . .
H2N H -0.0958(7) 0.107(2) 0.4694(9) 0.030(5) Uiso 1 1 d . . . . .
H17B H -0.1443(7) -0.1478(18) 0.4782(9) 0.024(4) Uiso 1 1 d . . . . .
H11 H -0.0593(7) -0.2595(19) 0.4515(10) 0.029(4) Uiso 1 1 d . . . . .
H19B H -0.2084(6) 0.0743(17) 0.4579(9) 0.022(4) Uiso 1 1 d . . . . .
H23A H -0.1434(7) 0.3112(18) 0.5911(10) 0.029(4) Uiso 1 1 d . . . . .
H3B H 0.2272(6) -0.2825(17) 0.1954(9) 0.022(4) Uiso 1 1 d . . . . .
H18A H -0.1481(7) 0.0697(19) 0.5980(10) 0.029(5) Uiso 1 1 d . . . . .
H23B H -0.1976(8) 0.3876(19) 0.5620(10) 0.033(5) Uiso 1 1 d . . . . .
H22B H -0.1249(7) 0.559(2) 0.5647(10) 0.032(5) Uiso 1 1 d . . . . .
H18B H -0.1924(7) -0.0492(18) 0.5798(9) 0.025(4) Uiso 1 1 d . . . . .
H1B H 0.3116(7) -0.210(2) 0.2678(10) 0.033(5) Uiso 1 1 d . . . . .
H4A H 0.1564(7) -0.111(2) 0.1538(10) 0.031(5) Uiso 1 1 d . . . . .
H20A H -0.1863(6) 0.2530(19) 0.3802(9) 0.026(4) Uiso 1 1 d . . . . .
H21A H -0.1118(7) 0.4220(18) 0.3872(9) 0.026(4) Uiso 1 1 d . . . . .
H20B H -0.2262(7) 0.3523(18) 0.4322(9) 0.029(4) Uiso 1 1 d . . . . .
H21B H -0.1674(7) 0.509(2) 0.3585(10) 0.035(5) Uiso 1 1 d . . . . .
H4B H 0.1339(7) -0.272(2) 0.1698(10) 0.032(5) Uiso 1 1 d . . . . .
H1C H 0.3135(9) -0.058(2) 0.3110(11) 0.051(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C6 1.2213(16) . ?
O1 C5 1.2237(17) . ?
N2 C12 1.3525(17) . ?
N2 C17 1.4559(18) . ?
N2 H2N 0.922(19) . ?
C8 C9 1.4140(19) . ?
C8 C7 1.4163(18) . ?
C8 C13 1.4217(18) . ?
N1 C6 1.3932(18) . ?
N1 C5 1.4094(18) . ?
N1 C4 1.4749(17) . ?
C7 C16 1.3808(19) . ?
C7 C6 1.4801(18) . ?
O3 C22 1.427(2) . ?
O3 C21 1.428(2) . ?
C9 C10 1.3851(19) . ?
C9 C5 1.4594(18) . ?
N3 C23 1.4632(19) . ?
N3 C20 1.4688(18) . ?
N3 C19 1.4796(19) . ?
C13 C14 1.4113(19) . ?
C13 C12 1.4452(18) . ?
C12 C11 1.400(2) . ?
C11 C10 1.384(2) . ?
C11 H11 0.960(18) . ?
C15 C14 1.3754(19) . ?
C15 C16 1.4016(19) . ?
C15 H15 0.950(16) . ?
C16 H16 0.952(16) . ?
C10 H10 0.958(16) . ?
C14 H14 1.057(15) . ?
C17 C18 1.526(2) . ?
C17 H17A 1.028(16) . ?
C17 H17B 1.039(17) . ?
C4 C3 1.524(2) . ?
C4 H4A 0.972(19) . ?
C4 H4B 0.969(18) . ?
C3 C2 1.522(2) . ?
C3 H3A 0.974(17) . ?
C3 H3B 0.995(16) . ?
C19 C18 1.520(2) . ?
C19 H19A 1.016(17) . ?
C19 H19B 1.025(16) . ?
C18 H18A 0.997(18) . ?
C18 H18B 0.973(17) . ?
C2 C1 1.524(2) . ?
C2 H2A 1.000(16) . ?
C2 H2B 1.001(16) . ?
C20 C21 1.508(2) . ?
C20 H20A 0.985(17) . ?
C20 H20B 1.027(17) . ?
C1 H1A 1.03(2) . ?
C1 H1B 0.989(19) . ?
C1 H1C 0.97(2) . ?
C23 C22 1.512(2) . ?
C23 H23A 0.963(18) . ?
C23 H23B 1.001(18) . ?
C22 H22A 0.971(16) . ?
C22 H22B 0.991(18) . ?
C21 H21A 1.021(17) . ?
C21 H21B 1.007(19) . ?

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 N2 C17 123.10(12) . . ?
C12 N2 H2N 119.4(11) . . ?
C17 N2 H2N 114.7(11) . . ?
C9 C8 C7 120.37(12) . . ?
C9 C8 C13 120.44(12) . . ?
C7 C8 C13 119.19(12) . . ?
C6 N1 C5 125.24(11) . . ?
C6 N1 C4 118.24(12) . . ?
C5 N1 C4 116.51(11) . . ?
C16 C7 C8 120.97(12) . . ?
C16 C7 C6 119.11(12) . . ?
C8 C7 C6 119.92(12) . . ?
C22 O3 C21 109.63(12) . . ?
C10 C9 C8 119.02(12) . . ?
C10 C9 C5 120.00(12) . . ?
C8 C9 C5 120.98(12) . . ?
C23 N3 C20 108.56(12) . . ?
C23 N3 C19 111.81(11) . . ?
C20 N3 C19 110.17(11) . . ?
C14 C13 C8 118.35(12) . . ?
C14 C13 C12 122.86(12) . . ?
C8 C13 C12 118.78(12) . . ?
N2 C12 C11 121.33(12) . . ?
N2 C12 C13 119.75(12) . . ?
C11 C12 C13 118.92(12) . . ?
O2 C6 N1 120.88(12) . . ?
O2 C6 C7 122.24(12) . . ?
N1 C6 C7 116.88(11) . . ?
C10 C11 C12 120.65(13) . . ?
C10 C11 H11 118.8(10) . . ?
C12 C11 H11 120.4(10) . . ?
C14 C15 C16 120.54(13) . . ?
C14 C15 H15 121.0(10) . . ?
C16 C15 H15 118.5(10) . . ?
C7 C16 C15 119.62(13) . . ?
C7 C16 H16 121.1(10) . . ?
C15 C16 H16 119.3(10) . . ?
C11 C10 C9 122.12(13) . . ?
C11 C10 H10 119.1(9) . . ?
C9 C10 H10 118.8(9) . . ?
O1 C5 N1 119.68(12) . . ?
O1 C5 C9 123.78(13) . . ?
N1 C5 C9 116.53(12) . . ?
C15 C14 C13 121.31(12) . . ?
C15 C14 H14 118.7(8) . . ?
C13 C14 H14 120.0(8) . . ?
N2 C17 C18 110.08(12) . . ?
N2 C17 H17A 108.9(9) . . ?
C18 C17 H17A 110.2(9) . . ?
N2 C17 H17B 109.7(9) . . ?
C18 C17 H17B 110.9(9) . . ?
H17A C17 H17B 107.0(13) . . ?
N1 C4 C3 112.19(11) . . ?
N1 C4 H4A 104.0(10) . . ?
C3 C4 H4A 112.1(10) . . ?
N1 C4 H4B 106.8(10) . . ?
C3 C4 H4B 109.8(10) . . ?
H4A C4 H4B 111.8(14) . . ?
C2 C3 C4 114.00(12) . . ?
C2 C3 H3A 110.3(10) . . ?
C4 C3 H3A 108.9(10) . . ?
C2 C3 H3B 107.7(9) . . ?
C4 C3 H3B 107.4(9) . . ?
H3A C3 H3B 108.4(13) . . ?
N3 C19 C18 112.76(11) . . ?
N3 C19 H19A 111.0(10) . . ?
C18 C19 H19A 109.0(9) . . ?
N3 C19 H19B 107.0(9) . . ?
C18 C19 H19B 111.2(9) . . ?
H19A C19 H19B 105.7(13) . . ?
C19 C18 C17 113.72(12) . . ?
C19 C18 H18A 109.5(10) . . ?
C17 C18 H18A 111.4(10) . . ?
C19 C18 H18B 109.6(10) . . ?
C17 C18 H18B 106.9(10) . . ?
H18A C18 H18B 105.3(14) . . ?
C3 C2 C1 112.58(13) . . ?
C3 C2 H2A 108.5(9) . . ?
C1 C2 H2A 110.8(9) . . ?
C3 C2 H2B 111.9(9) . . ?
C1 C2 H2B 109.0(9) . . ?
H2A C2 H2B 103.6(13) . . ?
N3 C20 C21 110.01(12) . . ?
N3 C20 H20A 108.0(10) . . ?
C21 C20 H20A 110.1(10) . . ?
N3 C20 H20B 109.4(9) . . ?
C21 C20 H20B 111.5(9) . . ?
H20A C20 H20B 107.7(13) . . ?
C2 C1 H1A 111.3(11) . . ?
C2 C1 H1B 109.5(10) . . ?
H1A C1 H1B 106.2(15) . . ?
C2 C1 H1C 113.0(12) . . ?
H1A C1 H1C 107.3(16) . . ?
H1B C1 H1C 109.4(16) . . ?
N3 C23 C22 110.30(13) . . ?
N3 C23 H23A 110.7(10) . . ?
C22 C23 H23A 109.4(10) . . ?
N3 C23 H23B 110.2(10) . . ?
C22 C23 H23B 109.6(10) . . ?
H23A C23 H23B 106.6(14) . . ?
O3 C22 C23 111.65(13) . . ?
O3 C22 H22A 108.2(9) . . ?
C23 C22 H22A 111.3(9) . . ?
O3 C22 H22B 106.1(10) . . ?
C23 C22 H22B 110.8(10) . . ?
H22A C22 H22B 108.5(14) . . ?
O3 C21 C20 111.72(13) . . ?
O3 C21 H21A 108.4(9) . . ?
C20 C21 H21A 110.9(10) . . ?
O3 C21 H21B 105.2(10) . . ?
C20 C21 H21B 111.8(10) . . ?
H21A C21 H21B 108.6(14) . . ?

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
C9 C8 C7 C16 -178.94(12) . . . . ?
C13 C8 C7 C16 1.38(18) . . . . ?
C9 C8 C7 C6 1.61(18) . . . . ?
C13 C8 C7 C6 -178.06(11) . . . . ?
C7 C8 C9 C10 -179.65(12) . . . . ?
C13 C8 C9 C10 0.02(19) . . . . ?
C7 C8 C9 C5 0.19(18) . . . . ?
C13 C8 C9 C5 179.86(11) . . . . ?
C9 C8 C13 C14 178.38(12) . . . . ?
C7 C8 C13 C14 -1.95(17) . . . . ?
C9 C8 C13 C12 -2.08(18) . . . . ?
C7 C8 C13 C12 177.59(11) . . . . ?
C17 N2 C12 C11 -4.34(19) . . . . ?
C17 N2 C12 C13 175.54(12) . . . . ?
C14 C13 C12 N2 2.76(19) . . . . ?
C8 C13 C12 N2 -176.76(11) . . . . ?
C14 C13 C12 C11 -177.35(12) . . . . ?
C8 C13 C12 C11 3.13(17) . . . . ?
C5 N1 C6 O2 -177.19(12) . . . . ?
C4 N1 C6 O2 1.12(18) . . . . ?
C5 N1 C6 C7 3.54(18) . . . . ?
C4 N1 C6 C7 -178.15(11) . . . . ?
C16 C7 C6 O2 -2.07(19) . . . . ?
C8 C7 C6 O2 177.39(12) . . . . ?
C16 C7 C6 N1 177.19(12) . . . . ?
C8 C7 C6 N1 -3.35(17) . . . . ?
N2 C12 C11 C10 177.71(12) . . . . ?
C13 C12 C11 C10 -2.18(19) . . . . ?
C8 C7 C16 C15 0.00(19) . . . . ?
C6 C7 C16 C15 179.45(12) . . . . ?
C14 C15 C16 C7 -0.8(2) . . . . ?
C12 C11 C10 C9 0.1(2) . . . . ?
C8 C9 C10 C11 1.0(2) . . . . ?
C5 C9 C10 C11 -178.81(12) . . . . ?
C6 N1 C5 O1 179.23(12) . . . . ?
C4 N1 C5 O1 0.90(18) . . . . ?
C6 N1 C5 C9 -1.81(18) . . . . ?
C4 N1 C5 C9 179.86(11) . . . . ?
C10 C9 C5 O1 -1.4(2) . . . . ?
C8 C9 C5 O1 178.72(13) . . . . ?
C10 C9 C5 N1 179.64(12) . . . . ?
C8 C9 C5 N1 -0.19(18) . . . . ?
C16 C15 C14 C13 0.2(2) . . . . ?
C8 C13 C14 C15 1.19(19) . . . . ?
C12 C13 C14 C15 -178.33(12) . . . . ?
C12 N2 C17 C18 -176.87(12) . . . . ?
C6 N1 C4 C3 99.74(15) . . . . ?
C5 N1 C4 C3 -81.81(15) . . . . ?
N1 C4 C3 C2 -69.97(16) . . . . ?
C23 N3 C19 C18 -77.62(15) . . . . ?
C20 N3 C19 C18 161.57(12) . . . . ?
N3 C19 C18 C17 -77.39(16) . . . . ?
N2 C17 C18 C19 55.77(16) . . . . ?
C4 C3 C2 C1 178.15(13) . . . . ?
C23 N3 C20 C21 57.46(16) . . . . ?
C19 N3 C20 C21 -179.79(12) . . . . ?
C20 N3 C23 C22 -57.32(16) . . . . ?
C19 N3 C23 C22 -179.06(12) . . . . ?
C21 O3 C22 C23 -57.47(17) . . . . ?
N3 C23 C22 O3 58.42(17) . . . . ?
C22 O3 C21 C20 57.85(17) . . . . ?
N3 C20 C21 O3 -58.78(17) . . . . ?

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.047


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_NIMC4
_database_code_depnum_ccdc_archive 'CCDC 2053602'
loop_
_audit_author_name
_audit_author_address
'Rohit Bhowal Deepak Chopra'
;IISER Bhopal
India
;
_audit_update_record             
;
2021-01-03 deposited with the CCDC.	2021-06-14 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         ?
_chemical_formula_sum            'C24 H31 N3 O3'
_chemical_formula_weight         409.52

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      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   8.6541(15)
_cell_length_b                   9.2597(18)
_cell_length_c                   13.842(3)
_cell_angle_alpha                104.249(8)
_cell_angle_beta                 97.838(8)
_cell_angle_gamma                96.127(8)
_cell_volume                     1053.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      30.03

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7052
_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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46934
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.294
_diffrn_reflns_theta_max         29.126
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5665
_reflns_number_gt                4456
_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)+(0.0600P)²+0.4104P] 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         5665
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.14584(11) 0.88511(10) 0.68397(7) 0.0170(2) Uani 1 1 d . . . . .
O2 O 0.11231(11) 0.51807(10) 0.84932(6) 0.0170(2) Uani 1 1 d . . . . .
O3 O 0.31638(11) 1.01941(10) 0.29638(7) 0.0187(2) Uani 1 1 d . . . . .
N1 N 0.12961(12) 0.70041(11) 0.76561(7) 0.0117(2) Uani 1 1 d . . . . .
N005 N 0.33095(11) 0.71179(11) 0.20151(7) 0.0116(2) Uani 1 1 d . . . . .
N2 N 0.27026(12) 0.33160(11) 0.33635(7) 0.0133(2) Uani 1 1 d . . . . .
H2N H 0.278323 0.239148 0.340147 0.016 Uiso 1 1 calc R U . . .
C8 C 0.18397(13) 0.48981(13) 0.59308(8) 0.0099(2) Uani 1 1 d . . . . .
C13 C 0.21344(13) 0.38255(13) 0.50713(8) 0.0108(2) Uani 1 1 d . . . . .
C6 C 0.13075(13) 0.55253(13) 0.77128(9) 0.0118(2) Uani 1 1 d . . . . .
C5 C 0.15162(13) 0.75190(13) 0.68030(9) 0.0118(2) Uani 1 1 d . . . . .
C12 C 0.24366(13) 0.43241(13) 0.41941(9) 0.0110(2) Uani 1 1 d . . . . .
C7 C 0.15563(13) 0.44224(13) 0.67965(8) 0.0105(2) Uani 1 1 d . . . . .
C11 C 0.24151(14) 0.58456(14) 0.42181(9) 0.0129(2) Uani 1 1 d . . . . .
H11 H 0.260891 0.618615 0.364595 0.015 Uiso 1 1 calc R U . . .
C17 C 0.28628(14) 0.36741(13) 0.24125(8) 0.0122(2) Uani 1 1 d . . . . .
H17B H 0.209164 0.435013 0.228457 0.015 Uiso 1 1 calc R U . . .
H17A H 0.259623 0.273346 0.185841 0.015 Uiso 1 1 calc R U . . .
C20 C 0.33909(14) 0.58598(14) 0.11505(9) 0.0134(2) Uani 1 1 d . . . . .
H20A H 0.365235 0.626269 0.058380 0.016 Uiso 1 1 calc R U . . .
H20B H 0.234376 0.522864 0.092561 0.016 Uiso 1 1 calc R U . . .
C21 C 0.18827(14) 0.77914(14) 0.18334(9) 0.0134(2) Uani 1 1 d . . . . .
H21A H 0.094187 0.701739 0.170036 0.016 Uiso 1 1 calc R U . . .
H21B H 0.189102 0.819010 0.123266 0.016 Uiso 1 1 calc R U . . .
C9 C 0.18286(13) 0.64220(13) 0.59256(9) 0.0109(2) Uani 1 1 d . . . . .
C10 C 0.21141(14) 0.68576(13) 0.50682(9) 0.0123(2) Uani 1 1 d . . . . .
H10 H 0.210286 0.788061 0.506347 0.015 Uiso 1 1 calc R U . . .
C3 C 0.26765(14) 0.90210(14) 0.91546(9) 0.0150(2) Uani 1 1 d . . . . .
H3B H 0.332662 0.931081 0.867788 0.018 Uiso 1 1 calc R U . . .
H3A H 0.324377 0.836357 0.949791 0.018 Uiso 1 1 calc R U . . .
C14 C 0.20747(15) 0.23080(14) 0.51019(9) 0.0144(2) Uani 1 1 d . . . . .
H14 H 0.224970 0.157632 0.452818 0.017 Uiso 1 1 calc R U . . .
C18 C 0.45114(14) 0.44279(14) 0.23859(9) 0.0128(2) Uani 1 1 d . . . . .
H18A H 0.527674 0.372713 0.246772 0.015 Uiso 1 1 calc R U . . .
H18B H 0.480799 0.533718 0.296321 0.015 Uiso 1 1 calc R U . . .
C15 C 0.17682(15) 0.18642(14) 0.59456(9) 0.0152(2) Uani 1 1 d . . . . .
H15 H 0.172012 0.083479 0.594651 0.018 Uiso 1 1 calc R U . . .
C19 C 0.46206(14) 0.48802(14) 0.14020(9) 0.0139(2) Uani 1 1 d . . . . .
H19B H 0.568517 0.543559 0.145580 0.017 Uiso 1 1 calc R U . . .
H19A H 0.449050 0.395621 0.083854 0.017 Uiso 1 1 calc R U . . .
C16 C 0.15280(14) 0.29342(14) 0.68011(9) 0.0129(2) Uani 1 1 d . . . . .
H16 H 0.134437 0.263170 0.738844 0.015 Uiso 1 1 calc R U . . .
C1 C 0.19380(15) 1.16653(14) 0.94759(10) 0.0179(3) Uani 1 1 d . . . . .
H1B H 0.275832 1.201769 0.912975 0.027 Uiso 1 1 calc R U . . .
H1A H 0.174430 1.250908 1.000865 0.027 Uiso 1 1 calc R U . . .
H1C H 0.096380 1.125787 0.898812 0.027 Uiso 1 1 calc R U . . .
C22 C 0.18091(14) 0.90567(14) 0.27522(10) 0.0154(2) Uani 1 1 d . . . . .
H22B H 0.084055 0.951125 0.262987 0.018 Uiso 1 1 calc R U . . .
H22A H 0.175964 0.864538 0.334498 0.018 Uiso 1 1 calc R U . . .
C4 C 0.10952(14) 0.81412(14) 0.85611(9) 0.0134(2) Uani 1 1 d . . . . .
H4B H 0.055420 0.763842 0.900221 0.016 Uiso 1 1 calc R U . . .
H4A H 0.042060 0.885009 0.835658 0.016 Uiso 1 1 calc R U . . .
C2 C 0.24777(15) 1.04399(14) 0.99438(9) 0.0164(2) Uani 1 1 d . . . . .
H2A H 0.169701 1.016773 1.035349 0.020 Uiso 1 1 calc R U . . .
H2B H 0.349575 1.084114 1.040360 0.020 Uiso 1 1 calc R U . . .
C24 C 0.46850(14) 0.82819(14) 0.22294(10) 0.0169(3) Uani 1 1 d . . . . .
H24B H 0.474327 0.868205 0.163268 0.020 Uiso 1 1 calc R U . . .
H24A H 0.565692 0.783918 0.236687 0.020 Uiso 1 1 calc R U . . .
C23 C 0.45744(15) 0.95503(15) 0.31352(10) 0.0199(3) Uani 1 1 d . . . . .
H23A H 0.458057 0.915989 0.374020 0.024 Uiso 1 1 calc R U . . .
H23B H 0.550255 1.033767 0.326541 0.024 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 1.2286(15) . ?
O2 C6 1.2248(14) . ?
O3 C23 1.4311(16) . ?
O3 C22 1.4354(15) . ?
N1 C6 1.3917(16) . ?
N1 C5 1.4062(15) . ?
N1 C4 1.4687(15) . ?
N005 C21 1.4607(15) . ?
N005 C24 1.4626(16) . ?
N005 C20 1.4658(15) . ?
N2 C12 1.3549(15) . ?
N2 C17 1.4549(15) . ?
N2 H2N 0.8800 . ?
C8 C9 1.4139(16) . ?
C8 C7 1.4167(16) . ?
C8 C13 1.4220(16) . ?
C13 C14 1.4118(17) . ?
C13 C12 1.4466(16) . ?
C6 C7 1.4771(16) . ?
C5 C9 1.4563(16) . ?
C12 C11 1.4033(16) . ?
C7 C16 1.3772(17) . ?
C11 C10 1.3869(16) . ?
C11 H11 0.9500 . ?
C17 C18 1.5292(16) . ?
C17 H17B 0.9900 . ?
C17 H17A 0.9900 . ?
C20 C19 1.5287(17) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.5161(17) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C9 C10 1.3880(16) . ?
C10 H10 0.9500 . ?
C3 C4 1.5288(17) . ?
C3 C2 1.5304(17) . ?
C3 H3B 0.9900 . ?
C3 H3A 0.9900 . ?
C14 C15 1.3786(17) . ?
C14 H14 0.9500 . ?
C18 C19 1.5318(16) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C15 C16 1.4003(17) . ?
C15 H15 0.9500 . ?
C19 H19B 0.9900 . ?
C19 H19A 0.9900 . ?
C16 H16 0.9500 . ?
C1 C2 1.5223(18) . ?
C1 H1B 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1C 0.9800 . ?
C22 H22B 0.9900 . ?
C22 H22A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 H4A 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C24 C23 1.5141(18) . ?
C24 H24B 0.9900 . ?
C24 H24A 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?

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
C23 O3 C22 110.07(9) . . ?
C6 N1 C5 125.05(10) . . ?
C6 N1 C4 118.32(10) . . ?
C5 N1 C4 116.59(10) . . ?
C21 N005 C24 109.05(10) . . ?
C21 N005 C20 110.74(9) . . ?
C24 N005 C20 111.70(9) . . ?
C12 N2 C17 123.77(10) . . ?
C12 N2 H2N 118.1 . . ?
C17 N2 H2N 118.1 . . ?
C9 C8 C7 120.18(10) . . ?
C9 C8 C13 120.64(10) . . ?
C7 C8 C13 119.18(10) . . ?
C14 C13 C8 118.37(10) . . ?
C14 C13 C12 122.81(10) . . ?
C8 C13 C12 118.80(10) . . ?
O2 C6 N1 120.60(11) . . ?
O2 C6 C7 122.65(11) . . ?
N1 C6 C7 116.75(10) . . ?
O1 C5 N1 119.06(11) . . ?
O1 C5 C9 123.90(11) . . ?
N1 C5 C9 117.03(10) . . ?
N2 C12 C11 121.44(10) . . ?
N2 C12 C13 119.69(10) . . ?
C11 C12 C13 118.86(10) . . ?
C16 C7 C8 120.66(11) . . ?
C16 C7 C6 119.12(10) . . ?
C8 C7 C6 120.22(10) . . ?
C10 C11 C12 120.70(11) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
N2 C17 C18 113.94(10) . . ?
N2 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
N2 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
H17B C17 H17A 107.7 . . ?
N005 C20 C19 112.49(10) . . ?
N005 C20 H20A 109.1 . . ?
C19 C20 H20A 109.1 . . ?
N005 C20 H20B 109.1 . . ?
C19 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
N005 C21 C22 109.45(10) . . ?
N005 C21 H21A 109.8 . . ?
C22 C21 H21A 109.8 . . ?
N005 C21 H21B 109.8 . . ?
C22 C21 H21B 109.8 . . ?
H21A C21 H21B 108.2 . . ?
C10 C9 C8 118.96(11) . . ?
C10 C9 C5 120.38(11) . . ?
C8 C9 C5 120.66(10) . . ?
C11 C10 C9 122.04(11) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C4 C3 C2 112.26(10) . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
H3B C3 H3A 107.9 . . ?
C15 C14 C13 121.49(11) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C17 C18 C19 112.86(10) . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C14 C15 C16 119.85(11) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C20 C19 C18 113.63(9) . . ?
C20 C19 H19B 108.8 . . ?
C18 C19 H19B 108.8 . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19A 108.8 . . ?
H19B C19 H19A 107.7 . . ?
C7 C16 C15 120.42(11) . . ?
C7 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1A 109.5 . . ?
H1B C1 H1A 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
O3 C22 C21 110.93(10) . . ?
O3 C22 H22B 109.5 . . ?
C21 C22 H22B 109.5 . . ?
O3 C22 H22A 109.5 . . ?
C21 C22 H22A 109.5 . . ?
H22B C22 H22A 108.0 . . ?
N1 C4 C3 111.75(10) . . ?
N1 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
N1 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
H4B C4 H4A 107.9 . . ?
C1 C2 C3 112.96(10) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N005 C24 C23 110.28(10) . . ?
N005 C24 H24B 109.6 . . ?
C23 C24 H24B 109.6 . . ?
N005 C24 H24A 109.6 . . ?
C23 C24 H24A 109.6 . . ?
H24B C24 H24A 108.1 . . ?
O3 C23 C24 110.78(10) . . ?
O3 C23 H23A 109.5 . . ?
C24 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.093


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       Luminescent
