# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_vc_152
_database_code_depnum_ccdc_archive 'CCDC 2456128'
loop_
_audit_author_name
_audit_author_address
'Kaushik Ghosh'
;Indian Institute of Technology Roorkee
India
;
_audit_update_record             
;
2025-06-02 deposited with the CCDC.	2026-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT213_vc_152              
;

PROBLEM:
Atom C41 has ADP max/min Ratio ..... 5.6 prolat
RESPONSE:
This alert is generated due to dynamic disorder in side-chain (tert-butyl group) of the structure and may be considered as a solvent.
;
_vrf_PLAT242_vc_152              
;

PROBLEM:
Low    'MainMol' Ueq as Compared to Neighbors of   C40 Check
RESPONSE:
This alert concerns side-chain atoms of the ligand; however this does not
indicate incorrect atom-type assignment.
;
_vrf_PLAT230_vc_152              
;

PROBLEM:
Hirshfeld Test Diff for    N011     --N3       .       11.0 s.u.
RESPONSE:
RIGU restraints were applied to atoms in the disordered
chains. Some of the atoms were still not ideally shaped, however, this
does not indicate an incorrect atom-type assignment.
;
_vrf_PLAT234_vc_152              
;

PROBLEM:
Large Hirshfeld Difference C40      --C41      .       0.27 Ang.
RESPONSE:
RIGU restraints were applied to atoms in the disordered
chains. Some of the atoms were still not ideally shaped, however, this
does not indicate an incorrect atom-type assignment.
;
_vrf_PLAT412_vc_152              
;

PROBLEM:
Short Intra XH3 .. XHn H41A ..H42A . 1.75 Ang.
x,y,z = 1_555 Check
RESPONSE:
This Alert is due to close contacts between protons of
highly disorderd methyls in tert-butyl group with high thermal parameters.
;
_audit_creation_date             2020-11-26
_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        ?
_chemical_formula_moiety         '0.13(C26 H30 N5 Ni O)'
_chemical_formula_sum            'C26 H30 N5 Ni O'
_chemical_formula_weight         487.24
_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'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.9839(5)
_cell_length_b                   9.4864(4)
_cell_length_c                   17.4810(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.127(2)
_cell_angle_gamma                90
_cell_volume                     2459.85(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    111
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.292
_cell_measurement_theta_min      1.14
_shelx_estimated_absorpt_T_max   0.765
_shelx_estimated_absorpt_T_min   0.765
_exptl_absorpt_coefficient_mu    0.816
_exptl_absorpt_correction_T_max  0.770
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            gray
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1028.0
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_standards_number         0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36056
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.292
_diffrn_reflns_theta_min         2.725
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa Apex'
_diffrn_measurement_method       'phi omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4305
_reflns_number_total             6092
_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       'Bruker Kappa Apex'
_computing_data_collection       'Bruker Kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.843
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         6092
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0525
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0844P)²+1.8159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1649
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), N011(H011), C16(H16), C14(H14), C11(H11), C8(H8), C4(H4A), C9(H9),
 C10(H10), C2(H2), C3(H3)
2.b Idealised Me refined as rotating group:
 C022(H02A,H02B,H02C), C029(H02D,H02E,H02F), C20(H20A,H20B,H20C), C41(H41A,
 H41B,H41C), C43(H43A,H43B,H43C), C42(H42A,H42B,H42C)
;
_atom_sites_solution_hydrogens   mixed
_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
Ni1 Ni 0.05671(2) 0.21466(3) 0.47789(2) 0.03493(13) Uani 1 1 d . . . . .
N4 N 0.02612(14) 0.3444(2) 0.54975(12) 0.0349(5) Uani 1 1 d . . . . .
O1 O 0.17938(13) 0.2489(2) 0.49852(12) 0.0449(5) Uani 1 1 d . . . . .
N3 N -0.06445(15) 0.1765(2) 0.45724(13) 0.0376(5) Uani 1 1 d . . . . .
C7 C 0.08263(18) 0.4253(3) 0.59303(15) 0.0384(6) Uani 1 1 d . . . . .
H7 H 0.058567 0.487330 0.625903 0.046 Uiso 1 1 calc R . . . .
N2 N -0.11049(16) 0.0901(3) 0.40902(13) 0.0435(6) Uani 1 1 d . . . . .
N1 N 0.08255(18) 0.0869(3) 0.40667(14) 0.0434(6) Uani 1 1 d . . . . .
C1 C 0.22219(18) 0.3370(3) 0.54812(16) 0.0386(6) Uani 1 1 d . . . . .
C2 C 0.17730(17) 0.4274(3) 0.59459(15) 0.0375(6) Uani 1 1 d . . . . .
C19 C 0.0272(2) 0.0042(3) 0.36059(15) 0.0418(6) Uani 1 1 d . . . . .
C8 C -0.06695(17) 0.3460(3) 0.55518(15) 0.0360(6) Uani 1 1 d . . . . .
C14 C -0.0679(2) 0.0077(3) 0.36239(16) 0.0437(7) Uani 1 1 d . . . . .
C13 C -0.11693(18) 0.2524(3) 0.50441(16) 0.0384(6) Uani 1 1 d . . . . .
C6 C 0.31871(18) 0.3433(3) 0.55666(16) 0.0410(6) Uani 1 1 d . . . . .
C4 C 0.31854(19) 0.5305(3) 0.65456(16) 0.0440(7) Uani 1 1 d . . . . .
C12 C -0.2097(2) 0.2379(3) 0.50426(19) 0.0489(7) Uani 1 1 d . . . . .
H12 H -0.242814 0.174544 0.470974 0.059 Uiso 1 1 calc R . . . .
C3 C 0.22672(19) 0.5233(3) 0.64685(16) 0.0428(6) Uani 1 1 d . . . . .
H3 H 0.195823 0.582390 0.676462 0.051 Uiso 1 1 calc R . . . .
C9 C -0.11013(19) 0.4268(3) 0.60579(18) 0.0461(7) Uani 1 1 d . . . . .
H9 H -0.077609 0.489977 0.639600 0.055 Uiso 1 1 calc R . . . .
C5 C 0.36166(19) 0.4392(3) 0.60908(17) 0.0448(7) Uani 1 1 d . . . . .
H5 H 0.424249 0.443123 0.614406 0.054 Uiso 1 1 calc R . . . .
C15 C -0.1258(2) -0.0839(3) 0.31250(18) 0.0554(8) Uani 1 1 d . . . . .
H15 H -0.187648 -0.081669 0.313645 0.066 Uiso 1 1 calc R . . . .
C18 C 0.0590(3) -0.0924(3) 0.30768(17) 0.0547(8) Uani 1 1 d . . . . .
H18 H 0.120396 -0.097260 0.304544 0.066 Uiso 1 1 calc R . . . .
C20 C 0.3715(2) 0.2450(4) 0.5094(2) 0.0525(8) Uani 1 1 d . . . . .
C10 C -0.2020(2) 0.4112(4) 0.60481(19) 0.0522(8) Uani 1 1 d . . . . .
H10 H -0.231185 0.463643 0.638766 0.063 Uiso 1 1 calc R . . . .
C16 C -0.0919(3) -0.1736(4) 0.26383(19) 0.0631(10) Uani 1 1 d . . . . .
H16 H -0.130363 -0.232444 0.231842 0.076 Uiso 1 1 calc R . . . .
C17 C 0.0006(3) -0.1776(4) 0.26165(19) 0.0613(9) Uani 1 1 d . . . . .
H17 H 0.023203 -0.239876 0.228036 0.074 Uiso 1 1 calc R . . . .
C24 C 0.3723(2) 0.6309(4) 0.71282(19) 0.0576(9) Uani 1 1 d . . . . .
C11 C -0.2512(2) 0.3186(4) 0.5539(2) 0.0557(8) Uani 1 1 d . . . . .
H11 H -0.313131 0.311092 0.553482 0.067 Uiso 1 1 calc R . . . .
C22 C 0.3453(3) 0.2710(5) 0.4232(2) 0.0689(10) Uani 1 1 d . . . . .
H22A H 0.281343 0.260220 0.409758 0.103 Uiso 1 1 calc GR . . . .
H22B H 0.375736 0.204347 0.394597 0.103 Uiso 1 1 calc GR . . . .
H22C H 0.362442 0.364953 0.410843 0.103 Uiso 1 1 calc GR . . . .
C23 C 0.4738(2) 0.2676(4) 0.5268(3) 0.0675(10) Uani 1 1 d . . . . .
H23A H 0.488246 0.361583 0.512238 0.101 Uiso 1 1 calc GR . . . .
H23B H 0.503911 0.200857 0.498072 0.101 Uiso 1 1 calc GR . . . .
H23C H 0.493297 0.254668 0.581097 0.101 Uiso 1 1 calc GR . . . .
C21 C 0.3532(3) 0.0904(4) 0.5298(3) 0.0827(13) Uani 1 1 d . . . . .
H21A H 0.374893 0.073924 0.583397 0.124 Uiso 1 1 calc GR . . . .
H21B H 0.383717 0.028698 0.498537 0.124 Uiso 1 1 calc GR . . . .
H21C H 0.289541 0.072457 0.520175 0.124 Uiso 1 1 calc GR . . . .
C27 C 0.4472(8) 0.6841(16) 0.6855(8) 0.385(13) Uani 1 1 d . . . . .
H27A H 0.463646 0.622970 0.646003 0.578 Uiso 1 1 calc GR . . . .
H27B H 0.496220 0.690197 0.727070 0.578 Uiso 1 1 calc GR . . . .
H27C H 0.433844 0.776327 0.664229 0.578 Uiso 1 1 calc GR . . . .
C26 C 0.4025(11) 0.5551(10) 0.7793(6) 0.402(12) Uani 1 1 d . . . . .
H26A H 0.384575 0.602299 0.823271 0.604 Uiso 1 1 calc GR . . . .
H26B H 0.467012 0.548144 0.785454 0.604 Uiso 1 1 calc GR . . . .
H26C H 0.376742 0.462214 0.775215 0.604 Uiso 1 1 calc GR . . . .
C25 C 0.3200(5) 0.7468(9) 0.7354(6) 0.231(6) Uani 1 1 d . . . . .
H25A H 0.261180 0.745436 0.705395 0.347 Uiso 1 1 calc GR . . . .
H25B H 0.349565 0.833924 0.726672 0.347 Uiso 1 1 calc GR . . . .
H25C H 0.314361 0.738481 0.789244 0.347 Uiso 1 1 calc GR . . . .
H1 H 0.135(2) 0.077(3) 0.4012(17) 0.043(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
Ni1 N4 1.862(2) . ?
Ni1 O1 1.851(2) . ?
Ni1 N3 1.836(2) . ?
Ni1 N1 1.818(3) . ?
N4 C7 1.303(3) . ?
N4 C8 1.411(3) . ?
O1 C1 1.306(3) . ?
N3 N2 1.302(3) . ?
N3 C13 1.414(4) . ?
C7 C2 1.415(4) . ?
N2 C14 1.352(4) . ?
N1 C19 1.328(4) . ?
C1 C2 1.415(4) . ?
C1 C6 1.434(4) . ?
C2 C3 1.421(4) . ?
C19 C14 1.431(4) . ?
C19 C18 1.430(4) . ?
C8 C13 1.396(4) . ?
C8 C9 1.396(4) . ?
C14 C15 1.433(4) . ?
C13 C12 1.396(4) . ?
C6 C5 1.384(4) . ?
C6 C20 1.537(4) . ?
C4 C3 1.365(4) . ?
C4 C5 1.394(4) . ?
C4 C24 1.537(4) . ?
C12 C11 1.370(5) . ?
C9 C10 1.382(4) . ?
C15 C16 1.351(5) . ?
C18 C17 1.367(5) . ?
C20 C22 1.524(5) . ?
C20 C23 1.535(5) . ?
C20 C21 1.543(5) . ?
C10 C11 1.386(5) . ?
C16 C17 1.393(5) . ?
C24 C27 1.377(7) . ?
C24 C26 1.387(9) . ?
C24 C25 1.437(7) . ?

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
O1 Ni1 N4 94.88(9) . . ?
N3 Ni1 N4 86.10(10) . . ?
N3 Ni1 O1 178.73(9) . . ?
N1 Ni1 N4 178.07(11) . . ?
N1 Ni1 O1 87.05(11) . . ?
N1 Ni1 N3 91.97(11) . . ?
C7 N4 Ni1 125.42(19) . . ?
C7 N4 C8 121.5(2) . . ?
C8 N4 Ni1 113.10(17) . . ?
C1 O1 Ni1 128.51(19) . . ?
N2 N3 Ni1 132.1(2) . . ?
N2 N3 C13 114.3(2) . . ?
C13 N3 Ni1 113.64(17) . . ?
N4 C7 C2 125.9(3) . . ?
N3 N2 C14 120.2(2) . . ?
C19 N1 Ni1 129.4(2) . . ?
O1 C1 C2 122.7(2) . . ?
O1 C1 C6 119.3(3) . . ?
C2 C1 C6 118.0(2) . . ?
C7 C2 C3 116.8(3) . . ?
C1 C2 C7 122.5(2) . . ?
C1 C2 C3 120.7(2) . . ?
N1 C19 C14 120.8(3) . . ?
N1 C19 C18 122.3(3) . . ?
C18 C19 C14 117.0(3) . . ?
C13 C8 N4 113.4(2) . . ?
C13 C8 C9 119.8(3) . . ?
C9 C8 N4 126.8(3) . . ?
N2 C14 C19 125.7(3) . . ?
N2 C14 C15 114.9(3) . . ?
C19 C14 C15 119.4(3) . . ?
C8 C13 N3 113.7(2) . . ?
C8 C13 C12 120.5(3) . . ?
C12 C13 N3 125.7(3) . . ?
C1 C6 C20 120.5(3) . . ?
C5 C6 C1 117.7(3) . . ?
C5 C6 C20 121.9(3) . . ?
C3 C4 C5 117.0(3) . . ?
C3 C4 C24 121.5(3) . . ?
C5 C4 C24 121.4(3) . . ?
C11 C12 C13 119.0(3) . . ?
C4 C3 C2 121.5(3) . . ?
C10 C9 C8 118.9(3) . . ?
C6 C5 C4 125.2(3) . . ?
C16 C15 C14 121.1(3) . . ?
C17 C18 C19 121.0(3) . . ?
C6 C20 C21 109.3(3) . . ?
C22 C20 C6 110.7(3) . . ?
C22 C20 C23 106.5(3) . . ?
C22 C20 C21 110.7(3) . . ?
C23 C20 C6 112.6(3) . . ?
C23 C20 C21 107.0(3) . . ?
C9 C10 C11 120.9(3) . . ?
C15 C16 C17 119.9(3) . . ?
C18 C17 C16 121.6(3) . . ?
C27 C24 C4 111.9(4) . . ?
C27 C24 C26 107.2(9) . . ?
C27 C24 C25 108.5(8) . . ?
C26 C24 C4 108.2(4) . . ?
C26 C24 C25 107.0(7) . . ?
C25 C24 C4 113.7(3) . . ?
C12 C11 C10 120.8(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_kg_vc_01_1253-423e191c
_database_code_depnum_ccdc_archive 'CCDC 2456129'
loop_
_audit_author_name
_audit_author_address
'Kaushik Ghosh'
;Indian Institute of Technology Roorkee
India
;
_audit_update_record             
;
2025-06-02 deposited with the CCDC.	2026-06-05 downloaded from the CCDC.
;
_audit_creation_date             2024-12-09
_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        ?
_chemical_formula_moiety         'C18 H17 N O2'
_chemical_formula_sum            'C18 H17 N O2'
_chemical_formula_weight         279.33
_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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   32.228(9)
_cell_length_b                   5.7311(13)
_cell_length_c                   16.854(5)
_cell_angle_alpha                90
_cell_angle_beta                 114.085(11)
_cell_angle_gamma                90
_cell_volume                     2841.9(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    98
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.267
_cell_measurement_theta_min      2.769
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark green'
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             169
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   0.967
_exptl_transmission_factor_min   0.437
_diffrn_reflns_av_R_equivalents  0.1048
_diffrn_reflns_av_unetI/netI     0.2049
_diffrn_reflns_Laue_measured_fraction_full 0.596
_diffrn_reflns_Laue_measured_fraction_max 0.597
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2523
_diffrn_reflns_point_group_measured_fraction_full 0.596
_diffrn_reflns_point_group_measured_fraction_max 0.597
_diffrn_reflns_theta_full        25.207
_diffrn_reflns_theta_max         25.207
_diffrn_reflns_theta_min         2.769
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.596
_diffrn_measured_fraction_theta_max 0.597
_diffrn_measurement_device_type  'Bruker Kappa Apex'
_diffrn_measurement_method       'phi omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                532
_reflns_number_total             1526
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.825
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         1526
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1540
_refine_ls_R_factor_gt           0.0601
_refine_ls_restrained_S_all      0.825
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1563
_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:
 C00K(H00E,H00F)
2.b Aromatic/amide H refined with riding coordinates:
 C004(H004), C005(H005), C009(H009), C00D(H00D), C00H(H00J), C00G(H00K),
 C00F(H00L), C00C(H00M), C00I(H00N)
2.c Idealised Me refined as rotating group:
 C00L(H00A,H00B,H00C), C00J(H00G,H00H,H00I)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O001 O 0.72561(13) 0.8252(6) 0.0770(3) 0.0273(12) Uani 1 1 d . . . . .
O002 O 0.53944(13) 0.7257(6) 0.5587(3) 0.0276(12) Uani 1 1 d . . . . .
N003 N 0.61629(16) 0.8277(7) 0.3205(4) 0.0211(13) Uani 1 1 d . . . . .
C004 C 0.63830(19) 0.4286(10) 0.4248(5) 0.0294(18) Uani 1 1 d . . . . .
H004 H 0.646103 0.291660 0.459635 0.035 Uiso 1 1 calc R . . . .
C005 C 0.69579(19) 0.5589(9) 0.2406(4) 0.0270(17) Uani 1 1 d . . . . .
H005 H 0.703628 0.420343 0.274467 0.032 Uiso 1 1 calc R . . . .
C006 C 0.7041(2) 0.8007(9) 0.1305(5) 0.0211(17) Uani 1 1 d . . . . .
C007 C 0.59766(19) 0.7914(9) 0.3786(5) 0.0232(17) Uani 1 1 d . . . . .
C008 C 0.64451(19) 0.6714(9) 0.3126(4) 0.0211(16) Uani 1 1 d . . . . .
C009 C 0.6559(2) 0.4648(9) 0.3655(5) 0.0274(17) Uani 1 1 d . . . . .
H009 H 0.676030 0.352923 0.358805 0.033 Uiso 1 1 calc R . . . .
C00D C 0.67322(19) 0.9564(9) 0.1386(5) 0.0281(17) Uani 1 1 d . . . . .
H00D H 0.665140 1.093146 0.103700 0.034 Uiso 1 1 calc R . . . .
C00L C 0.5288(2) 0.5818(10) 0.6807(5) 0.0342(18) Uani 1 1 d . . . . .
H00A H 0.495800 0.578283 0.647292 0.051 Uiso 1 1 calc GR . . . .
H00B H 0.537844 0.735029 0.708172 0.051 Uiso 1 1 calc GR . . . .
H00C H 0.537589 0.460691 0.725676 0.051 Uiso 1 1 calc GR . . . .
C00K C 0.5521(2) 0.5377(10) 0.6210(5) 0.0319(18) Uani 1 1 d . . . . .
H00E H 0.585505 0.534244 0.654299 0.038 Uiso 1 1 calc R . . . .
H00F H 0.542333 0.386062 0.590953 0.038 Uiso 1 1 calc R . . . .
C00J C 0.7190(2) 1.0377(10) 0.0288(5) 0.0362(19) Uani 1 1 d . . . . .
H00G H 0.686655 1.055836 -0.009136 0.054 Uiso 1 1 calc GR . . . .
H00H H 0.736648 1.032877 -0.006710 0.054 Uiso 1 1 calc GR . . . .
H00I H 0.729060 1.169805 0.069057 0.054 Uiso 1 1 calc GR . . . .
C00H C 0.71499(19) 0.6035(9) 0.1826(5) 0.0231(17) Uani 1 1 d . . . . .
H00J H 0.736371 0.495847 0.178269 0.028 Uiso 1 1 calc R . . . .
C00G C 0.58981(17) 0.5648(9) 0.4972(4) 0.0207(16) Uani 1 1 d . . . . .
H00K H 0.597787 0.433889 0.535106 0.025 Uiso 1 1 calc R . . . .
C00F C 0.5665(2) 0.9529(10) 0.3876(5) 0.0315(18) Uani 1 1 d . . . . .
H00L H 0.558567 1.086970 0.351292 0.038 Uiso 1 1 calc R . . . .
C00C C 0.65402(19) 0.9137(9) 0.1975(4) 0.0220(16) Uani 1 1 d . . . . .
H00M H 0.632864 1.022421 0.202109 0.026 Uiso 1 1 calc R . . . .
C00A C 0.55974(19) 0.7314(10) 0.5019(5) 0.0272(19) Uani 1 1 d . . . . .
C00B C 0.66503(18) 0.7147(9) 0.2501(5) 0.0232(18) Uani 1 1 d . . . . .
C00E C 0.60830(18) 0.5934(9) 0.4352(4) 0.0210(16) Uani 1 1 d . . . . .
C00I C 0.5479(2) 0.9250(10) 0.4448(5) 0.0272(18) Uani 1 1 d . . . . .
H00N H 0.526530 1.036000 0.447136 0.033 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C006 1.351(8) . ?
O001 C00J 1.431(6) . ?
O002 C00K 1.443(7) . ?
O002 C00A 1.362(8) . ?
N003 C007 1.358(8) . ?
N003 C008 1.322(7) . ?
C004 C009 1.353(9) . ?
C004 C00E 1.413(8) . ?
C005 C00H 1.377(9) . ?
C005 C00B 1.391(8) . ?
C006 C00D 1.384(8) . ?
C006 C00H 1.386(8) . ?
C007 C00F 1.417(8) . ?
C007 C00E 1.431(8) . ?
C008 C009 1.437(8) . ?
C008 C00B 1.475(10) . ?
C00D C00C 1.389(9) . ?
C00L C00K 1.504(9) . ?
C00G C00A 1.385(8) . ?
C00G C00E 1.408(9) . ?
C00F C00I 1.338(9) . ?
C00C C00B 1.399(8) . ?
C00A C00I 1.415(9) . ?

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
C006 O001 C00J 118.0(5) . . ?
C00A O002 C00K 117.0(5) . . ?
C008 N003 C007 119.6(5) . . ?
C009 C004 C00E 120.3(6) . . ?
C00H C005 C00B 120.7(6) . . ?
O001 C006 C00D 125.7(6) . . ?
O001 C006 C00H 116.2(5) . . ?
C00D C006 C00H 118.0(7) . . ?
N003 C007 C00F 121.1(6) . . ?
N003 C007 C00E 123.1(6) . . ?
C00F C007 C00E 115.7(7) . . ?
N003 C008 C009 120.6(6) . . ?
N003 C008 C00B 119.0(5) . . ?
C009 C008 C00B 120.4(6) . . ?
C004 C009 C008 120.4(6) . . ?
C006 C00D C00C 120.3(6) . . ?
O002 C00K C00L 106.9(5) . . ?
C005 C00H C006 122.0(6) . . ?
C00A C00G C00E 118.6(6) . . ?
C00I C00F C007 123.0(6) . . ?
C00D C00C C00B 121.7(6) . . ?
O002 C00A C00G 124.8(6) . . ?
O002 C00A C00I 115.0(6) . . ?
C00G C00A C00I 120.2(7) . . ?
C005 C00B C008 121.5(5) . . ?
C005 C00B C00C 117.3(6) . . ?
C00C C00B C008 121.2(5) . . ?
C004 C00E C007 115.9(6) . . ?
C00G C00E C004 122.2(6) . . ?
C00G C00E C007 121.9(6) . . ?
C00F C00I C00A 120.5(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
