# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

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

data_mo_gs_ps_p4_141
_database_code_depnum_ccdc_archive 'CCDC 2402030'
loop_
_audit_author_name
_audit_author_address
'Punith S'
;IIT Hyderabad
India
;
_audit_update_record             
;
2024-11-12 deposited with the CCDC.	2025-05-05 downloaded from the CCDC.
;
_audit_creation_date             2024-07-23
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H21 N O'
_chemical_formula_sum            'C16 H21 N O'
_chemical_formula_weight         243.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   19.461(3)
_cell_length_b                   7.0742(11)
_cell_length_c                   10.8476(15)
_cell_angle_alpha                90
_cell_angle_beta                 103.577(10)
_cell_angle_gamma                90
_cell_volume                     1451.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2734
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.695
_cell_measurement_theta_min      2.153
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1539 before and 0.0847 after correction.
The Ratio of minimum to maximum transmission is 0.7038.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16148
_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         27.089
_diffrn_reflns_theta_min         2.533
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-IV Photon II'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1035
_reflns_number_total             1720
_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 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1720
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.031
_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)+(0.0666P)²+0.4089P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1505
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H16A(0.5) H16B(0.5) H16C(0.5) H2A(0.5) H2B(0.5) H2C(0.5) H1A(0.5)
 H1B(0.5) H1C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C3(H3)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C2(H2A,H2B,H2C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_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
O001 O 0.92999(9) 0.500000 0.84440(18) 0.0756(7) Uani 1 2 d S T P . .
N002 N 0.84541(9) 0.500000 0.95969(17) 0.0499(6) Uani 1 2 d S T P . .
C10 C 0.80279(11) 0.500000 0.7423(2) 0.0454(6) Uani 1 2 d S T P . .
C7 C 0.74348(11) 0.500000 0.8045(2) 0.0453(6) Uani 1 2 d S T P . .
C8 C 0.77153(11) 0.500000 0.9343(2) 0.0451(6) Uani 1 2 d S T P . .
C9 C 0.86779(12) 0.500000 0.8488(2) 0.0510(6) Uani 1 2 d S T P . .
C6 C 0.67087(12) 0.500000 0.7590(2) 0.0537(7) Uani 1 2 d S T P . .
H6 H 0.651659 0.500000 0.671974 0.064 Uiso 1 2 calc R U P . .
C11 C 0.79790(12) 0.500000 0.6172(2) 0.0507(6) Uani 1 2 d S T P . .
H11 H 0.751682 0.500000 0.568539 0.061 Uiso 1 2 calc R U P . .
C3 C 0.72877(13) 0.500000 1.0194(2) 0.0551(7) Uani 1 2 d S T P . .
H3 H 0.748482 0.500000 1.106258 0.066 Uiso 1 2 calc R U P . .
C4 C 0.65539(13) 0.500000 0.9731(3) 0.0570(7) Uani 1 2 d S T P . .
C5 C 0.62627(13) 0.500000 0.8425(3) 0.0570(7) Uani 1 2 d S T P . .
C12 C 0.85313(13) 0.500000 0.5401(2) 0.0589(7) Uani 1 2 d S T P . .
C16 C 0.89201(14) 0.500000 1.0847(2) 0.0631(8) Uani 1 2 d S T P . .
H16A H 0.878020 0.598111 1.134862 0.095 Uiso 0.5 1 calc R U P A -1
H16B H 0.939659 0.522063 1.077931 0.095 Uiso 0.5 1 calc R U P A -1
H16C H 0.889337 0.379826 1.124410 0.095 Uiso 0.5 1 calc R U P A -1
C13 C 0.8144(2) 0.500000 0.3992(3) 0.0818(10) Uani 1 2 d S T P . .
C15 C 0.89832(15) 0.6783(5) 0.5675(3) 0.0880(9) Uani 1 1 d . . . . .
C2 C 0.54748(13) 0.500000 0.7889(3) 0.0821(10) Uani 1 2 d S T P . .
H2A H 0.537553 0.467420 0.700553 0.123 Uiso 0.5 1 calc R U P B -1
H2B H 0.528894 0.623440 0.798419 0.123 Uiso 0.5 1 calc R U P B -1
H2C H 0.525789 0.409141 0.833512 0.123 Uiso 0.5 1 calc R U P B -1
C1 C 0.60928(16) 0.500000 1.0669(3) 0.0827(10) Uani 1 2 d S T P . .
H1A H 0.637987 0.479852 1.150728 0.124 Uiso 0.5 1 calc R U P C -1
H1B H 0.574904 0.400654 1.045959 0.124 Uiso 0.5 1 calc R U P C -1
H1C H 0.585541 0.619493 1.063624 0.124 Uiso 0.5 1 calc R U P C -1
H13A H 0.8527(17) 0.500000 0.348(3) 0.098(10) Uiso 1 2 d S . P . .
H15A H 0.9267(12) 0.677(3) 0.655(2) 0.105(8) Uiso 1 1 d . . . . .
H13B H 0.7790(12) 0.618(4) 0.375(2) 0.114(8) Uiso 1 1 d . . . . .
H15B H 0.9309(13) 0.682(4) 0.513(2) 0.123(9) Uiso 1 1 d . . . . .
H15C H 0.8657(14) 0.803(4) 0.553(3) 0.132(11) 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
O001 C9 1.223(3) . ?
N002 C8 1.399(3) . ?
N002 C9 1.372(3) . ?
N002 C16 1.443(3) . ?
C10 C7 1.468(3) . ?
C10 C9 1.500(3) . ?
C10 C11 1.337(3) . ?
C7 C8 1.386(3) . ?
C7 C6 1.383(3) . ?
C8 C3 1.380(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.394(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.509(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.398(3) . ?
C4 C5 1.397(4) . ?
C4 C1 1.506(4) . ?
C5 C2 1.507(4) . ?
C12 C13 1.537(4) . ?
C12 C15 1.526(3) 6_565 ?
C12 C15 1.526(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C13 H13A 1.03(3) . ?
C13 H13B 1.07(2) . ?
C15 H15A 0.98(2) . ?
C15 H15B 0.96(2) . ?
C15 H15C 1.08(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N002 C16 125.1(2) . . ?
C9 N002 C8 110.54(19) . . ?
C9 N002 C16 124.4(2) . . ?
C7 C10 C9 104.91(19) . . ?
C11 C10 C7 126.2(2) . . ?
C11 C10 C9 128.9(2) . . ?
C8 C7 C10 107.64(19) . . ?
C6 C7 C10 133.1(2) . . ?
C6 C7 C8 119.3(2) . . ?
C7 C8 N002 109.95(19) . . ?
C3 C8 N002 128.4(2) . . ?
C3 C8 C7 121.6(2) . . ?
O001 C9 N002 123.7(2) . . ?
O001 C9 C10 129.3(2) . . ?
N002 C9 C10 106.96(19) . . ?
C7 C6 H6 119.8 . . ?
C7 C6 C5 120.5(2) . . ?
C5 C6 H6 119.8 . . ?
C10 C11 H11 113.9 . . ?
C10 C11 C12 132.2(2) . . ?
C12 C11 H11 113.9 . . ?
C8 C3 H3 120.5 . . ?
C8 C3 C4 119.0(2) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C1 118.6(3) . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 C1 121.4(3) . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 C2 118.8(3) . . ?
C4 C5 C2 121.7(2) . . ?
C11 C12 C13 107.7(2) . . ?
C11 C12 C15 110.15(16) . 6_565 ?
C11 C12 C15 110.15(15) . . ?
C15 C12 C13 108.65(17) . . ?
C15 C12 C13 108.65(17) 6_565 . ?
C15 C12 C15 111.4(3) . 6_565 ?
N002 C16 H16A 109.5 . . ?
N002 C16 H16B 109.5 . . ?
N002 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C13 H13A 106.6(18) . . ?
C12 C13 H13B 112.1(13) . . ?
H13A C13 H13B 112.0(16) . . ?
C12 C15 H15A 110.4(14) . . ?
C12 C15 H15B 109.6(16) . . ?
C12 C15 H15C 110.8(14) . . ?
H15A C15 H15B 107(2) . . ?
H15A C15 H15C 109(2) . . ?
H15B C15 H15C 110(2) . . ?
C5 C2 H2A 109.5 . . ?
C5 C2 H2B 109.5 . . ?
C5 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

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
N002 C8 C3 C4 180.000(1) . . . . ?
C10 C7 C8 N002 0.000(1) . . . . ?
C10 C7 C8 C3 180.000(1) . . . . ?
C10 C7 C6 C5 180.000(1) . . . . ?
C10 C11 C12 C13 180.000(1) . . . . ?
C10 C11 C12 C15 61.67(18) . . . 6_565 ?
C10 C11 C12 C15 -61.67(18) . . . . ?
C7 C10 C9 O001 180.000(1) . . . . ?
C7 C10 C9 N002 0.000(1) . . . . ?
C7 C10 C11 C12 180.000(1) . . . . ?
C7 C8 C3 C4 0.000(1) . . . . ?
C7 C6 C5 C4 0.000(1) . . . . ?
C7 C6 C5 C2 180.000(1) . . . . ?
C8 N002 C9 O001 180.000(1) . . . . ?
C8 N002 C9 C10 0.000(1) . . . . ?
C8 C7 C6 C5 0.000(1) . . . . ?
C8 C3 C4 C5 0.000(1) . . . . ?
C8 C3 C4 C1 180.000(1) . . . . ?
C9 N002 C8 C7 0.000(1) . . . . ?
C9 N002 C8 C3 180.000(1) . . . . ?
C9 C10 C7 C8 0.000(1) . . . . ?
C9 C10 C7 C6 180.000(1) . . . . ?
C9 C10 C11 C12 0.000(1) . . . . ?
C6 C7 C8 N002 180.000(1) . . . . ?
C6 C7 C8 C3 0.000(1) . . . . ?
C11 C10 C7 C8 180.000(1) . . . . ?
C11 C10 C7 C6 0.000(1) . . . . ?
C11 C10 C9 O001 0.000(1) . . . . ?
C11 C10 C9 N002 180.000(1) . . . . ?
C3 C4 C5 C6 0.000(1) . . . . ?
C3 C4 C5 C2 180.000(1) . . . . ?
C16 N002 C8 C7 180.000(1) . . . . ?
C16 N002 C8 C3 0.000(1) . . . . ?
C16 N002 C9 O001 0.000(1) . . . . ?
C16 N002 C9 C10 180.000(1) . . . . ?
C1 C4 C5 C6 180.000(1) . . . . ?
C1 C4 C5 C2 0.000(1) . . . . ?

_olex2_exptl_crystal_mounting_method 'Nylon loop used'
_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_mo_gs_ps_142_1
_database_code_depnum_ccdc_archive 'CCDC 2428258'
loop_
_audit_author_name
_audit_author_address
'Ramana babu'
;IITH
India
;
_audit_update_record             
;
2025-03-03 deposited with the CCDC.	2025-05-05 downloaded from the CCDC.
;
_audit_creation_date             2025-03-03
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2025.02.27 svn.r83f5de26 for OlexSys, GUI svn.r7172)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 I N O'
_chemical_formula_sum            'C10 H8 I N O'
_chemical_formula_weight         285.07
_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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.9735(16)
_cell_length_b                   11.629(2)
_cell_length_c                   8.9604(16)
_cell_angle_alpha                90
_cell_angle_beta                 98.377(6)
_cell_angle_gamma                90
_cell_volume                     1028.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9783
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.091
_cell_measurement_theta_min      2.708
_shelx_estimated_absorpt_T_max   0.709
_shelx_estimated_absorpt_T_min   0.358
_exptl_absorpt_coefficient_mu    3.074
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.3585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1171 before and 0.0734 after correction.
The Ratio of minimum to maximum transmission is 0.4809.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14723
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.133
_diffrn_reflns_theta_min         2.707
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-V Photon II'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2065
_reflns_number_total             2247
_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 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.033
_refine_diff_density_min         -0.979
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       0.067(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.067
_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)+(0.0255P)²+1.5809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0813
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C10(H10)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
2.c :
 C9(H9)
;
_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
I1 I -0.08847(3) 0.84486(2) 0.33844(3) 0.06314(17) Uani 1 1 d . . . . .
O1 O 0.6119(3) 0.5249(3) 0.7711(3) 0.0689(8) Uani 1 1 d . . . . .
N1 N 0.3881(3) 0.5638(2) 0.7051(3) 0.0479(6) Uani 1 1 d . . . . .
C9 C 0.5903(4) 0.7170(4) 0.4898(6) 0.0690(11) Uani 1 1 d . . . . .
H9 H 0.621172 0.767134 0.421486 0.083 Uiso 1 1 calc R U . . .
C1 C 0.0745(3) 0.7524(3) 0.4562(4) 0.0431(7) Uani 1 1 d . . . . .
C2 C 0.1665(4) 0.8077(3) 0.5610(4) 0.0489(8) Uani 1 1 d . . . . .
H2 H 0.159231 0.886450 0.576089 0.059 Uiso 1 1 calc R U . . .
C3 C 0.2703(4) 0.7456(3) 0.6443(4) 0.0487(8) Uani 1 1 d . . . . .
H3 H 0.331235 0.781835 0.717897 0.058 Uiso 1 1 calc R U . . .
C4 C 0.2824(3) 0.6293(3) 0.6170(4) 0.0407(6) Uani 1 1 d . . . . .
C7 C 0.5199(3) 0.5753(3) 0.6917(4) 0.0469(7) Uani 1 1 d . . . . .
C8 C 0.5513(4) 0.6538(3) 0.5758(5) 0.0514(8) Uani 1 1 d . . . . .
C6 C 0.3486(5) 0.4828(4) 0.8163(5) 0.0763(13) Uani 1 1 d . . . . .
H6A H 0.340221 0.523142 0.907997 0.114 Uiso 1 1 calc R U . . .
H6B H 0.416429 0.424036 0.836544 0.114 Uiso 1 1 calc R U . . .
H6C H 0.263277 0.448204 0.777316 0.114 Uiso 1 1 calc R U . . .
C5 C 0.1905(4) 0.5744(3) 0.5097(4) 0.0484(8) Uani 1 1 d . . . . .
H5 H 0.199314 0.496233 0.491763 0.058 Uiso 1 1 calc R U . . .
C10 C 0.0853(4) 0.6362(3) 0.4291(4) 0.0478(7) Uani 1 1 d . . . . .
H10 H 0.022611 0.599799 0.357532 0.057 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
I1 C1 2.101(3) . ?
O1 C7 1.226(4) . ?
N1 C4 1.440(4) . ?
N1 C7 1.343(5) . ?
N1 C6 1.466(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.171(6) . ?
C1 C2 1.373(5) . ?
C1 C10 1.380(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(4) . ?
C4 C5 1.384(5) . ?
C7 C8 1.451(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C10 1.384(5) . ?
C10 H10 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C6 117.7(3) . . ?
C7 N1 C4 123.1(3) . . ?
C7 N1 C6 119.2(3) . . ?
C8 C9 H9 180.0 . . ?
C2 C1 I1 119.7(2) . . ?
C2 C1 C10 121.2(3) . . ?
C10 C1 I1 119.2(3) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.7(3) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 N1 119.8(3) . . ?
C3 C4 C5 120.5(3) . . ?
C5 C4 N1 119.6(3) . . ?
O1 C7 N1 124.1(4) . . ?
O1 C7 C8 119.6(3) . . ?
N1 C7 C8 116.3(3) . . ?
C9 C8 C7 173.1(4) . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C10 119.9(3) . . ?
C10 C5 H5 120.1 . . ?
C1 C10 C5 119.3(3) . . ?
C1 C10 H10 120.4 . . ?
C5 C10 H10 120.4 . . ?

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
I1 C1 C2 C3 176.8(3) . . . . ?
I1 C1 C10 C5 -178.2(3) . . . . ?
N1 C4 C5 C10 177.3(3) . . . . ?
C1 C2 C3 C4 2.2(5) . . . . ?
C2 C1 C10 C5 0.3(5) . . . . ?
C2 C3 C4 N1 -178.7(3) . . . . ?
C2 C3 C4 C5 -1.3(5) . . . . ?
C3 C4 C5 C10 -0.1(5) . . . . ?
C4 N1 C7 O1 175.9(3) . . . . ?
C4 N1 C7 C8 -3.5(5) . . . . ?
C4 C5 C10 C1 0.6(5) . . . . ?
C7 N1 C4 C3 -70.6(4) . . . . ?
C7 N1 C4 C5 111.9(4) . . . . ?
C6 N1 C4 C3 108.0(4) . . . . ?
C6 N1 C4 C5 -69.4(5) . . . . ?
C6 N1 C7 O1 -2.7(6) . . . . ?
C6 N1 C7 C8 177.9(4) . . . . ?
C10 C1 C2 C3 -1.7(5) . . . . ?

_olex2_exptl_crystal_mounting_method 'Nylon loop used'
_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_mo_gs_ps_p4me_2
_database_code_depnum_ccdc_archive 'CCDC 2402041'
loop_
_audit_author_name
_audit_author_address
'Punith S'
;IIT Hyderabad
India
;
_audit_update_record             
;
2024-11-12 deposited with the CCDC.	2025-05-05 downloaded from the CCDC.
;
_audit_creation_date             2024-11-12
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.11.02 svn.r19aeb66f for OlexSys, GUI svn.r7078)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H15 N O3'
_chemical_formula_sum            'C13 H15 N O3'
_chemical_formula_weight         233.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.1369(3)
_cell_length_b                   9.3444(5)
_cell_length_c                   25.1733(16)
_cell_angle_alpha                90
_cell_angle_beta                 92.300(2)
_cell_angle_gamma                90
_cell_volume                     1207.38(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3808
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.554
_cell_measurement_theta_min      2.716
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0890 before and 0.0661 after correction.
The Ratio of minimum to maximum transmission is 0.7096.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear brownish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            16379
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.142
_diffrn_reflns_theta_min         2.325
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-V Photon II'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1835
_reflns_number_total             2675
_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 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2675
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0536
_refine_ls_restrained_S_all      1.023
_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)+(0.0599P)²+0.4193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1483
_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 Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C6(H6)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C1(H1A,H1B,H1C), C13(H13A,H13B,H13C)
;
_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
O1 O 0.9134(3) 0.39236(15) 0.75046(6) 0.0598(4) Uani 1 1 d . . . . .
O3 O -0.1081(3) 0.34028(17) 0.54966(6) 0.0647(5) Uani 1 1 d . . . . .
O2 O 0.3978(4) 0.73898(18) 0.62653(7) 0.0845(6) Uani 1 1 d . . . . .
N1 N 0.1552(3) 0.20710(17) 0.60599(7) 0.0498(4) Uani 1 1 d . . . . .
C12 C 0.6067(6) 0.7608(3) 0.54492(12) 0.0888(9) Uani 1 1 d . . . . .
H12A H 0.512996 0.764543 0.511174 0.133 Uiso 1 1 calc R U . . .
H12B H 0.767534 0.710221 0.541152 0.133 Uiso 1 1 calc R U . . .
H12C H 0.642821 0.856349 0.557138 0.133 Uiso 1 1 calc R U . . .
C11 C 0.4456(4) 0.6849(2) 0.58434(9) 0.0551(5) Uani 1 1 d . . . . .
C10 C 0.3487(4) 0.5406(2) 0.56783(8) 0.0474(5) Uani 1 1 d . . . . .
H10A H 0.495092 0.485162 0.555929 0.057 Uiso 1 1 calc R U . . .
H10B H 0.227272 0.552105 0.537629 0.057 Uiso 1 1 calc R U . . .
C9 C 0.2146(4) 0.4549(2) 0.61041(7) 0.0446(5) Uani 1 1 d . . . . .
H9 H 0.096033 0.517103 0.629372 0.053 Uiso 1 1 calc R U . . .
C4 C 0.3972(3) 0.37956(19) 0.64980(7) 0.0410(4) Uani 1 1 d . . . . .
C3 C 0.5829(4) 0.4295(2) 0.68544(7) 0.0454(5) Uani 1 1 d . . . . .
H3 H 0.611124 0.527384 0.689166 0.055 Uiso 1 1 calc R U . . .
C2 C 0.7302(4) 0.3324(2) 0.71623(7) 0.0449(5) Uani 1 1 d . . . . .
C1 C 1.0741(4) 0.2978(3) 0.78152(9) 0.0609(6) Uani 1 1 d . . . . .
H1A H 1.164755 0.234834 0.758456 0.091 Uiso 1 1 calc R U . . .
H1B H 0.967944 0.242402 0.804383 0.091 Uiso 1 1 calc R U . . .
H1C H 1.198114 0.352256 0.802684 0.091 Uiso 1 1 calc R U . . .
C7 C 0.6873(4) 0.1867(2) 0.71110(8) 0.0513(5) Uani 1 1 d . . . . .
H7 H 0.786712 0.122744 0.731686 0.062 Uiso 1 1 calc R U . . .
C6 C 0.4950(4) 0.1352(2) 0.67508(8) 0.0531(5) Uani 1 1 d . . . . .
H6 H 0.463178 0.037591 0.671657 0.064 Uiso 1 1 calc R U . . .
C5 C 0.3542(3) 0.2330(2) 0.64487(7) 0.0436(4) Uani 1 1 d . . . . .
C8 C 0.0622(4) 0.3311(2) 0.58472(8) 0.0488(5) Uani 1 1 d . . . . .
C13 C 0.0578(5) 0.0678(2) 0.59028(11) 0.0702(7) Uani 1 1 d . . . . .
H13A H -0.097136 0.078816 0.568042 0.105 Uiso 1 1 calc R U . . .
H13B H 0.018053 0.013809 0.621371 0.105 Uiso 1 1 calc R U . . .
H13C H 0.187668 0.018242 0.570997 0.105 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 C2 1.370(2) . ?
O1 C1 1.422(2) . ?
O3 C8 1.221(2) . ?
O2 C11 1.210(3) . ?
N1 C5 1.408(2) . ?
N1 C8 1.356(3) . ?
N1 C13 1.444(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 C11 1.496(3) . ?
C11 C10 1.491(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.525(3) . ?
C9 H9 0.9800 . ?
C9 C4 1.511(3) . ?
C9 C8 1.525(3) . ?
C4 C3 1.366(3) . ?
C4 C5 1.392(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.396(3) . ?
C2 C7 1.385(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C7 H7 0.9300 . ?
C7 C6 1.399(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.375(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 117.43(17) . . ?
C5 N1 C13 125.40(17) . . ?
C8 N1 C5 111.24(16) . . ?
C8 N1 C13 123.35(18) . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
O2 C11 C12 121.4(2) . . ?
O2 C11 C10 123.0(2) . . ?
C10 C11 C12 115.5(2) . . ?
C11 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C11 C10 C9 115.75(17) . . ?
H10A C10 H10B 107.4 . . ?
C9 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
C10 C9 H9 109.8 . . ?
C10 C9 C8 109.81(15) . . ?
C4 C9 C10 114.82(15) . . ?
C4 C9 H9 109.8 . . ?
C4 C9 C8 102.69(15) . . ?
C8 C9 H9 109.8 . . ?
C3 C4 C9 132.14(17) . . ?
C3 C4 C5 119.94(17) . . ?
C5 C4 C9 107.92(16) . . ?
C4 C3 H3 120.3 . . ?
C4 C3 C2 119.42(18) . . ?
C2 C3 H3 120.3 . . ?
O1 C2 C3 115.25(17) . . ?
O1 C2 C7 124.31(18) . . ?
C7 C2 C3 120.44(18) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C7 H7 119.9 . . ?
C2 C7 C6 120.27(18) . . ?
C6 C7 H7 119.9 . . ?
C7 C6 H6 120.9 . . ?
C5 C6 C7 118.16(18) . . ?
C5 C6 H6 120.9 . . ?
C4 C5 N1 109.82(16) . . ?
C6 C5 N1 128.42(18) . . ?
C6 C5 C4 121.76(18) . . ?
O3 C8 N1 125.2(2) . . ?
O3 C8 C9 126.45(19) . . ?
N1 C8 C9 108.30(16) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C7 C6 179.84(18) . . . . ?
O2 C11 C10 C9 -7.9(3) . . . . ?
C12 C11 C10 C9 172.5(2) . . . . ?
C11 C10 C9 C4 -80.5(2) . . . . ?
C11 C10 C9 C8 164.46(16) . . . . ?
C10 C9 C4 C3 61.3(3) . . . . ?
C10 C9 C4 C5 -117.55(18) . . . . ?
C10 C9 C8 O3 -56.7(3) . . . . ?
C10 C9 C8 N1 120.87(17) . . . . ?
C9 C4 C3 C2 -178.06(18) . . . . ?
C9 C4 C5 N1 -1.0(2) . . . . ?
C9 C4 C5 C6 178.93(17) . . . . ?
C4 C9 C8 O3 -179.29(19) . . . . ?
C4 C9 C8 N1 -1.70(19) . . . . ?
C4 C3 C2 O1 179.40(17) . . . . ?
C4 C3 C2 C7 -0.5(3) . . . . ?
C3 C4 C5 N1 -179.99(16) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C3 C2 C7 C6 -0.2(3) . . . . ?
C2 C7 C6 C5 0.8(3) . . . . ?
C1 O1 C2 C3 -178.06(17) . . . . ?
C1 O1 C2 C7 1.9(3) . . . . ?
C7 C6 C5 N1 179.21(18) . . . . ?
C7 C6 C5 C4 -0.6(3) . . . . ?
C5 N1 C8 O3 178.87(19) . . . . ?
C5 N1 C8 C9 1.2(2) . . . . ?
C5 C4 C3 C2 0.7(3) . . . . ?
C8 N1 C5 C4 -0.2(2) . . . . ?
C8 N1 C5 C6 179.94(19) . . . . ?
C8 C9 C4 C3 -179.55(19) . . . . ?
C8 C9 C4 C5 1.58(19) . . . . ?
C13 N1 C5 C4 -179.8(2) . . . . ?
C13 N1 C5 C6 0.3(3) . . . . ?
C13 N1 C8 O3 -1.5(3) . . . . ?
C13 N1 C8 C9 -179.13(19) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop used'
_olex2_submission_special_instructions 'No special instructions were received'
