# Electronic Supplementary Material (ESI) for ChemComm.
# 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_24auga_0m
_database_code_depnum_ccdc_archive 'CCDC 2110289'
loop_
_audit_author_name
_audit_author_address
'Rajib Mandal'
;IIT Kanpur
India
;
_audit_update_record             
;
2021-09-16 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_audit_creation_date             2021-09-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        5AC
_chemical_formula_moiety         'C31 H36 N2 O3'
_chemical_formula_sum            'C31 H36 N2 O3'
_chemical_formula_weight         484.62
_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                   8.2757(6)
_cell_length_b                   12.3903(9)
_cell_length_c                   13.7007(10)
_cell_angle_alpha                106.492(2)
_cell_angle_beta                 95.327(2)
_cell_angle_gamma                97.944(2)
_cell_volume                     1321.16(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    273
_cell_measurement_theta_max      28.317
_cell_measurement_theta_min      2.510
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1009 before and 0.0646 after correction. The Ratio of minimum to maximum transmission is 0.8647. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_preparation       'Cobalt cataluzed annulation'
_exptl_crystal_recrystallization_method 
'Slow Evaporation in dichloromethane solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33836
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.340
_diffrn_reflns_theta_min         2.509
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5179
_reflns_number_total             6569
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         6569
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.046
_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)+(0.0347P)²+0.9323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1179
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C26(H26A,H26B), C25(H25A,H25B), C29(H29A,H29B), C28(H28A,
 H28B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C12(H12), C15(H15), C16(H16), C17(H17), C6(H6), C4(H4),
 C5(H5)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C31(H31A,H31B,H31C), C30(H30A,H30B,H30C), C22(H22A,H22B,
 H22C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.37156(12) 0.67341(8) 0.70666(7) 0.0165(2) Uani 1 1 d . . . . .
O3 O 0.10729(13) 0.67905(9) 0.73219(8) 0.0237(2) Uani 1 1 d . . . . .
O1 O 0.31439(14) 0.31446(9) 0.74313(8) 0.0244(2) Uani 1 1 d . . . . .
N1 N 0.32686(14) 0.48831(10) 0.71918(8) 0.0151(2) Uani 1 1 d . . . . .
N2 N 0.64759(15) 0.57840(11) 0.81276(9) 0.0193(3) Uani 1 1 d . . . . .
C9 C 0.33084(16) 0.55737(11) 0.65505(10) 0.0150(3) Uani 1 1 d . . . . .
C18 C 0.52654(17) 0.58647(11) 0.87440(10) 0.0159(3) Uani 1 1 d . . . . .
C7 C 0.27743(16) 0.39423(12) 0.50684(10) 0.0148(3) Uani 1 1 d . . . . .
C8 C 0.30799(16) 0.51726(12) 0.55221(10) 0.0151(3) Uani 1 1 d . . . . .
C10 C 0.36090(17) 0.54019(11) 0.82912(10) 0.0157(3) Uani 1 1 d . . . . .
C14 C 0.55832(18) 0.64022(12) 0.98241(10) 0.0178(3) Uani 1 1 d . . . . .
C2 C 0.27389(16) 0.32044(12) 0.56939(10) 0.0154(3) Uani 1 1 d . . . . .
C1 C 0.30568(17) 0.36950(12) 0.68174(10) 0.0166(3) Uani 1 1 d . . . . .
C11 C 0.23581(18) 0.54485(12) 0.88761(11) 0.0185(3) Uani 1 1 d . . . . .
H11 H 0.128021 0.514211 0.856573 0.022 Uiso 1 1 calc R . . . .
C19 C 0.24543(17) 0.72813(12) 0.74301(10) 0.0172(3) Uani 1 1 d . . . . .
C24 C 0.31383(17) 0.59649(12) 0.48653(11) 0.0172(3) Uani 1 1 d . . . . .
H24A H 0.376941 0.568621 0.431225 0.021 Uiso 1 1 calc R . . . .
H24B H 0.371425 0.671484 0.527986 0.021 Uiso 1 1 calc R . . . .
C13 C 0.42682(19) 0.64285(12) 1.04184(11) 0.0202(3) Uani 1 1 d . . . . .
H13 H 0.447708 0.676464 1.112689 0.024 Uiso 1 1 calc R . . . .
C3 C 0.24349(17) 0.20013(12) 0.52355(11) 0.0186(3) Uani 1 1 d . . . . .
C12 C 0.26955(19) 0.59616(13) 0.99533(11) 0.0214(3) Uani 1 1 d . . . . .
H12 H 0.183814 0.598090 1.034795 0.026 Uiso 1 1 calc R . . . .
C15 C 0.72335(19) 0.68919(13) 1.02603(11) 0.0218(3) Uani 1 1 d . . . . .
H15 H 0.749907 0.725541 1.096287 0.026 Uiso 1 1 calc R . . . .
C16 C 0.84309(19) 0.68221(14) 0.96323(12) 0.0252(3) Uani 1 1 d . . . . .
H16 H 0.952142 0.714541 0.990050 0.030 Uiso 1 1 calc R . . . .
C26 C 0.15509(18) 0.66386(12) 0.35338(11) 0.0194(3) Uani 1 1 d . . . . .
H26A H 0.215309 0.620853 0.302770 0.023 Uiso 1 1 calc R . . . .
H26B H 0.044839 0.659243 0.319723 0.023 Uiso 1 1 calc R . . . .
C17 C 0.79892(19) 0.62527(14) 0.85713(12) 0.0237(3) Uani 1 1 d . . . . .
H17 H 0.882309 0.620542 0.815812 0.028 Uiso 1 1 calc R . . . .
C25 C 0.14340(17) 0.60848(13) 0.43972(11) 0.0189(3) Uani 1 1 d . . . . .
H25A H 0.075057 0.533481 0.412783 0.023 Uiso 1 1 calc R . . . .
H25B H 0.090890 0.654521 0.493171 0.023 Uiso 1 1 calc R . . . .
C6 C 0.25452(17) 0.34651(13) 0.39927(11) 0.0188(3) Uani 1 1 d . . . . .
H6 H 0.259686 0.394071 0.357537 0.023 Uiso 1 1 calc R . . . .
C29 C 0.13295(19) 0.84208(13) 0.23062(12) 0.0234(3) Uani 1 1 d . . . . .
H29A H 0.054924 0.880793 0.269956 0.028 Uiso 1 1 calc R . . . .
H29B H 0.078739 0.764513 0.194202 0.028 Uiso 1 1 calc R . . . .
C28 C 0.28107(19) 0.83881(13) 0.30408(11) 0.0218(3) Uani 1 1 d . . . . .
H28A H 0.341059 0.916085 0.334655 0.026 Uiso 1 1 calc R . . . .
H28B H 0.353796 0.794351 0.264619 0.026 Uiso 1 1 calc R . . . .
C4 C 0.21731(19) 0.15813(13) 0.41721(11) 0.0226(3) Uani 1 1 d . . . . .
H4 H 0.194189 0.079515 0.386045 0.027 Uiso 1 1 calc R . . . .
C20 C 0.30942(19) 0.85427(12) 0.79473(11) 0.0212(3) Uani 1 1 d . . . . .
C5 C 0.22470(19) 0.23048(13) 0.35580(11) 0.0233(3) Uani 1 1 d . . . . .
H5 H 0.209227 0.199671 0.284630 0.028 Uiso 1 1 calc R . . . .
C27 C 0.23983(19) 0.78862(13) 0.39041(11) 0.0221(3) Uani 1 1 d . . . . .
H27A H 0.340915 0.795039 0.435175 0.027 Uiso 1 1 calc R . . . .
H27B H 0.168880 0.833843 0.430864 0.027 Uiso 1 1 calc R . . . .
C23 C 0.4590(2) 0.86902(14) 0.87557(12) 0.0276(3) Uani 1 1 d . . . . .
H23A H 0.426370 0.834920 0.927038 0.041 Uiso 1 1 calc GR . . . .
H23B H 0.500792 0.948930 0.907184 0.041 Uiso 1 1 calc GR . . . .
H23C H 0.543288 0.832429 0.843004 0.041 Uiso 1 1 calc GR . . . .
C31 C 0.2392(2) 0.11532(13) 0.58366(12) 0.0255(3) Uani 1 1 d . . . . .
H31A H 0.346442 0.122957 0.620864 0.038 Uiso 1 1 calc GR . . . .
H31B H 0.207753 0.039249 0.537249 0.038 Uiso 1 1 calc GR . . . .
H31C H 0.160746 0.129715 0.631151 0.038 Uiso 1 1 calc GR . . . .
C30 C 0.1816(2) 0.90327(14) 0.15269(12) 0.0275(3) Uani 1 1 d . . . . .
H30A H 0.084634 0.905432 0.109529 0.041 Uiso 1 1 calc GR . . . .
H30B H 0.254460 0.862980 0.111161 0.041 Uiso 1 1 calc GR . . . .
H30C H 0.236432 0.979852 0.188376 0.041 Uiso 1 1 calc GR . . . .
C22 C 0.3604(2) 0.90763(14) 0.71165(13) 0.0320(4) Uani 1 1 d . . . . .
H22A H 0.447731 0.873028 0.681049 0.048 Uiso 1 1 calc GR . . . .
H22B H 0.397802 0.988249 0.742090 0.048 Uiso 1 1 calc GR . . . .
H22C H 0.267622 0.895021 0.659774 0.048 Uiso 1 1 calc GR . . . .
C21 C 0.1730(2) 0.90975(15) 0.84583(16) 0.0382(4) Uani 1 1 d . . . . .
H21A H 0.081244 0.901884 0.794557 0.057 Uiso 1 1 calc GR . . . .
H21B H 0.213639 0.989344 0.879953 0.057 Uiso 1 1 calc GR . . . .
H21C H 0.138356 0.872945 0.895144 0.057 Uiso 1 1 calc GR . . . .


_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 C9 1.3876(16) . ?
O2 C19 1.3776(17) . ?
O3 C19 1.1933(17) . ?
O1 C1 1.2271(16) . ?
N1 C9 1.3891(17) . ?
N1 C10 1.4432(17) . ?
N1 C1 1.3943(17) . ?
N2 C18 1.3651(18) . ?
N2 C17 1.3162(19) . ?
C9 C8 1.3398(19) . ?
C18 C10 1.4197(19) . ?
C18 C14 1.4221(19) . ?
C7 C8 1.4492(19) . ?
C7 C2 1.4189(18) . ?
C7 C6 1.4072(19) . ?
C8 C24 1.5075(18) . ?
C10 C11 1.3643(19) . ?
C14 C13 1.417(2) . ?
C14 C15 1.416(2) . ?
C2 C1 1.4688(19) . ?
C2 C3 1.4196(19) . ?
C11 C12 1.415(2) . ?
C19 C20 1.516(2) . ?
C24 C25 1.5384(19) . ?
C13 C12 1.365(2) . ?
C3 C4 1.386(2) . ?
C3 C31 1.507(2) . ?
C15 C16 1.367(2) . ?
C16 C17 1.411(2) . ?
C26 C25 1.5308(19) . ?
C26 C27 1.526(2) . ?
C6 C5 1.368(2) . ?
C29 C28 1.525(2) . ?
C29 C30 1.527(2) . ?
C28 C27 1.528(2) . ?
C4 C5 1.392(2) . ?
C20 C23 1.536(2) . ?
C20 C22 1.533(2) . ?
C20 C21 1.525(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
C19 O2 C9 116.90(11) . . ?
C9 N1 C10 119.51(11) . . ?
C9 N1 C1 122.57(11) . . ?
C1 N1 C10 117.67(11) . . ?
C17 N2 C18 117.10(12) . . ?
O2 C9 N1 114.07(11) . . ?
C8 C9 O2 121.90(12) . . ?
C8 C9 N1 123.91(12) . . ?
N2 C18 C10 118.90(12) . . ?
N2 C18 C14 122.98(13) . . ?
C10 C18 C14 118.12(12) . . ?
C2 C7 C8 120.97(12) . . ?
C6 C7 C8 119.92(12) . . ?
C6 C7 C2 119.09(12) . . ?
C9 C8 C7 117.04(12) . . ?
C9 C8 C24 121.53(12) . . ?
C7 C8 C24 121.43(12) . . ?
C18 C10 N1 118.53(12) . . ?
C11 C10 N1 120.35(13) . . ?
C11 C10 C18 121.11(13) . . ?
C13 C14 C18 119.80(13) . . ?
C15 C14 C18 117.51(13) . . ?
C15 C14 C13 122.69(13) . . ?
C7 C2 C1 119.50(12) . . ?
C7 C2 C3 120.16(12) . . ?
C3 C2 C1 120.32(12) . . ?
O1 C1 N1 118.91(12) . . ?
O1 C1 C2 125.24(13) . . ?
N1 C1 C2 115.85(11) . . ?
C10 C11 C12 120.21(14) . . ?
O2 C19 C20 110.24(12) . . ?
O3 C19 O2 122.35(13) . . ?
O3 C19 C20 127.41(13) . . ?
C8 C24 C25 114.10(11) . . ?
C12 C13 C14 120.14(13) . . ?
C2 C3 C31 123.89(13) . . ?
C4 C3 C2 118.11(13) . . ?
C4 C3 C31 118.01(13) . . ?
C13 C12 C11 120.59(13) . . ?
C16 C15 C14 118.95(13) . . ?
C15 C16 C17 119.09(14) . . ?
C27 C26 C25 113.57(12) . . ?
N2 C17 C16 124.36(14) . . ?
C26 C25 C24 111.98(11) . . ?
C5 C6 C7 120.30(13) . . ?
C28 C29 C30 112.27(13) . . ?
C29 C28 C27 115.12(13) . . ?
C3 C4 C5 121.75(13) . . ?
C19 C20 C23 109.60(12) . . ?
C19 C20 C22 107.81(12) . . ?
C19 C20 C21 109.12(13) . . ?
C22 C20 C23 109.93(13) . . ?
C21 C20 C23 110.02(14) . . ?
C21 C20 C22 110.32(14) . . ?
C6 C5 C4 120.55(13) . . ?
C26 C27 C28 114.25(12) . . ?

_olex2_submission_original_sample_id BSRM-3890
_olex2_submission_special_instructions 'No special instructions were received'
