# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc24ffbc
_database_code_depnum_ccdc_archive 'CCDC 1979112'
loop_
_audit_author_name
_audit_author_address
'Alex Andrews P'
;IISER Thiruvananthapuram
India
;
_audit_update_record             
;
2020-01-21 deposited with the CCDC.	2020-04-08 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         'C27 H33 N O '
_chemical_formula_sum            'C27 H33 N O'
_chemical_formula_weight         387.54

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.3170(9)
_cell_length_b                   18.704(2)
_cell_length_c                   13.6865(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.967(4)
_cell_angle_gamma                90
_cell_volume                     2379.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6384
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      22.02

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.081
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.082
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.064
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            32653
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.178
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4184
_reflns_number_gt                2711
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3- 2014.1(Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0570P)²+1.2432P] 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         4184
_refine_ls_number_parameters     269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1646
_refine_ls_wR_factor_gt          0.1319
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
C1 C 0.4275(2) 0.32796(12) 0.27819(16) 0.0469(5) Uani 1 1 d . . . . .
C2 C 0.3877(2) 0.36511(12) 0.19345(15) 0.0483(6) Uani 1 1 d . . . . .
H2 H 0.425698 0.410512 0.185133 0.058 Uiso 1 1 calc R U . . .
C3 C 0.2930(2) 0.33730(12) 0.11995(15) 0.0450(5) Uani 1 1 d . . . . .
C4 C 0.2364(2) 0.26913(12) 0.13614(15) 0.0478(6) Uani 1 1 d . . . . .
C5 C 0.2792(2) 0.22857(12) 0.21873(17) 0.0502(6) Uani 1 1 d . . . . .
C6 C 0.3742(2) 0.26004(12) 0.28844(16) 0.0501(6) Uani 1 1 d . . . . .
H6 H 0.402954 0.234147 0.344415 0.060 Uiso 1 1 calc R U . . .
C7 C 0.2543(3) 0.37944(13) 0.02546(16) 0.0568(6) Uani 1 1 d . . . . .
C8 C 0.0972(4) 0.4023(2) 0.0213(2) 0.1134(14) Uani 1 1 d . . . . .
H8A H 0.075042 0.429885 -0.037007 0.170 Uiso 1 1 calc R U . . .
H8B H 0.080641 0.430812 0.077728 0.170 Uiso 1 1 calc R U . . .
H8C H 0.036841 0.360695 0.020408 0.170 Uiso 1 1 calc R U . . .
C9 C 0.2812(4) 0.33561(17) -0.06523(19) 0.0849(9) Uani 1 1 d . . . . .
H9A H 0.217712 0.295122 -0.069034 0.127 Uiso 1 1 calc R U . . .
H9B H 0.379161 0.319374 -0.061231 0.127 Uiso 1 1 calc R U . . .
H9C H 0.263640 0.364699 -0.122605 0.127 Uiso 1 1 calc R U . . .
C10 C 0.3469(4) 0.44630(17) 0.0192(2) 0.1065(13) Uani 1 1 d . . . . .
H10A H 0.446657 0.433098 0.024541 0.160 Uiso 1 1 calc R U . . .
H10B H 0.327610 0.478280 0.071576 0.160 Uiso 1 1 calc R U . . .
H10C H 0.324573 0.469626 -0.042477 0.160 Uiso 1 1 calc R U . . .
C11 C 0.2259(3) 0.15193(15) 0.2348(2) 0.0736(8) Uani 1 1 d . . . . .
C12 C 0.2549(5) 0.10439(18) 0.1464(3) 0.1240(15) Uani 1 1 d . . . . .
H12A H 0.355804 0.105086 0.136214 0.186 Uiso 1 1 calc R U . . .
H12B H 0.201516 0.122184 0.089007 0.186 Uiso 1 1 calc R U . . .
H12C H 0.225490 0.056251 0.158956 0.186 Uiso 1 1 calc R U . . .
C13 C 0.0659(4) 0.1530(2) 0.2524(3) 0.1106(13) Uani 1 1 d . . . . .
H13A H 0.035912 0.106007 0.270420 0.166 Uiso 1 1 calc R U . . .
H13B H 0.011823 0.167730 0.193542 0.166 Uiso 1 1 calc R U . . .
H13C H 0.049353 0.185966 0.304163 0.166 Uiso 1 1 calc R U . . .
C14 C 0.3053(5) 0.11736(18) 0.3238(3) 0.1313(17) Uani 1 1 d . . . . .
H14A H 0.407007 0.123712 0.320289 0.197 Uiso 1 1 calc R U . . .
H14B H 0.283327 0.067229 0.324796 0.197 Uiso 1 1 calc R U . . .
H14C H 0.275396 0.139388 0.382445 0.197 Uiso 1 1 calc R U . . .
C15 C 0.5223(2) 0.36099(12) 0.36175(16) 0.0494(6) Uani 1 1 d . . . . .
H15 H 0.560577 0.321109 0.402047 0.059 Uiso 1 1 calc R U . . .
C16 C 0.6508(3) 0.40001(13) 0.32640(16) 0.0529(6) Uani 1 1 d . . . . .
C17 C 0.7593(3) 0.36049(16) 0.2890(2) 0.0743(8) Uani 1 1 d . . . . .
H17 H 0.750990 0.310957 0.286628 0.089 Uiso 1 1 calc R U . . .
C18 C 0.8796(4) 0.3922(2) 0.2551(2) 0.0956(10) Uani 1 1 d . . . . .
H18 H 0.951260 0.364367 0.230187 0.115 Uiso 1 1 calc R U . . .
C19 C 0.8927(4) 0.4652(2) 0.2583(2) 0.0966(11) Uani 1 1 d . . . . .
H19 H 0.972529 0.487210 0.234266 0.116 Uiso 1 1 calc R U . . .
C20 C 0.7894(4) 0.50509(19) 0.2965(3) 0.0980(11) Uani 1 1 d . . . . .
H20 H 0.799759 0.554483 0.300326 0.118 Uiso 1 1 calc R U . . .
C21 C 0.6683(3) 0.47296(15) 0.3299(2) 0.0776(8) Uani 1 1 d . . . . .
H21 H 0.597515 0.501208 0.355150 0.093 Uiso 1 1 calc R U . . .
C22 C 0.4319(3) 0.40627(14) 0.42769(18) 0.0632(7) Uani 1 1 d . . . . .
H22A H 0.494860 0.427432 0.479235 0.076 Uiso 1 1 calc R U . . .
H22B H 0.387312 0.444889 0.389273 0.076 Uiso 1 1 calc R U . . .
C23 C 0.3172(3) 0.36421(15) 0.47318(18) 0.0637(7) Uani 1 1 d . . . . .
C24 C 0.1738(3) 0.3755(2) 0.4497(2) 0.0926(10) Uani 1 1 d . . . . .
H24 H 0.144617 0.410969 0.405013 0.111 Uiso 1 1 calc R U . . .
C25 C 0.0733(4) 0.3346(3) 0.4923(3) 0.1192(15) Uani 1 1 d . . . . .
H25 H -0.024259 0.341393 0.475805 0.143 Uiso 1 1 calc R U . . .
C26 C 0.1169(4) 0.2848(3) 0.5576(3) 0.1164(14) Uani 1 1 d . . . . .
H26 H 0.050718 0.257381 0.589056 0.140 Uiso 1 1 calc R U . . .
C27 C 0.2595(4) 0.2754(2) 0.5767(3) 0.1124(13) Uani 1 1 d . . . . .
H27 H 0.289460 0.239478 0.620533 0.135 Uiso 1 1 calc R U . . .
N1 N 0.3604(2) 0.31425(15) 0.53685(18) 0.0852(8) Uani 1 1 d . . . . .
O1 O 0.1429(2) 0.24288(13) 0.06327(12) 0.0920(7) Uani 1 1 d . . . . .
H1 H 0.071782 0.226381 0.087342 0.138 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
C1 C6 1.375(3) . ?
C1 C2 1.380(3) . ?
C1 C15 1.527(3) . ?
C2 C3 1.392(3) . ?
C3 C4 1.403(3) . ?
C3 C7 1.536(3) . ?
C4 O1 1.369(3) . ?
C4 C5 1.396(3) . ?
C5 C6 1.387(3) . ?
C5 C11 1.538(3) . ?
C7 C8 1.522(4) . ?
C7 C9 1.523(4) . ?
C7 C10 1.525(4) . ?
C11 C14 1.525(4) . ?
C11 C13 1.526(4) . ?
C11 C12 1.540(5) . ?
C15 C16 1.510(3) . ?
C15 C22 1.532(3) . ?
C16 C21 1.375(4) . ?
C16 C17 1.379(4) . ?
C17 C18 1.376(4) . ?
C18 C19 1.371(5) . ?
C19 C20 1.351(5) . ?
C20 C21 1.384(4) . ?
C22 C23 1.497(4) . ?
C23 N1 1.321(3) . ?
C23 C24 1.369(4) . ?
C24 C25 1.371(5) . ?
C25 C26 1.334(6) . ?
C26 C27 1.348(5) . ?
C27 N1 1.335(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
C6 C1 C2 118.2(2) . . ?
C6 C1 C15 119.47(19) . . ?
C2 C1 C15 122.25(19) . . ?
C1 C2 C3 122.6(2) . . ?
C2 C3 C4 116.9(2) . . ?
C2 C3 C7 121.1(2) . . ?
C4 C3 C7 122.00(19) . . ?
O1 C4 C5 121.8(2) . . ?
O1 C4 C3 116.0(2) . . ?
C5 C4 C3 122.13(19) . . ?
C6 C5 C4 117.3(2) . . ?
C6 C5 C11 119.6(2) . . ?
C4 C5 C11 123.0(2) . . ?
C1 C6 C5 122.7(2) . . ?
C8 C7 C9 109.4(2) . . ?
C8 C7 C10 108.3(3) . . ?
C9 C7 C10 105.7(2) . . ?
C8 C7 C3 110.2(2) . . ?
C9 C7 C3 111.6(2) . . ?
C10 C7 C3 111.5(2) . . ?
C14 C11 C13 107.7(3) . . ?
C14 C11 C5 111.5(2) . . ?
C13 C11 C5 109.8(3) . . ?
C14 C11 C12 106.3(3) . . ?
C13 C11 C12 111.0(3) . . ?
C5 C11 C12 110.5(2) . . ?
C16 C15 C1 112.71(18) . . ?
C16 C15 C22 113.70(19) . . ?
C1 C15 C22 110.61(19) . . ?
C21 C16 C17 117.2(2) . . ?
C21 C16 C15 124.3(2) . . ?
C17 C16 C15 118.5(2) . . ?
C18 C17 C16 121.9(3) . . ?
C19 C18 C17 119.4(3) . . ?
C20 C19 C18 119.9(3) . . ?
C19 C20 C21 120.5(3) . . ?
C16 C21 C20 121.1(3) . . ?
C23 C22 C15 113.1(2) . . ?
N1 C23 C24 120.8(3) . . ?
N1 C23 C22 116.9(2) . . ?
C24 C23 C22 122.3(3) . . ?
C23 C24 C25 119.9(3) . . ?
C26 C25 C24 119.3(3) . . ?
C25 C26 C27 118.1(4) . . ?
N1 C27 C26 124.2(4) . . ?
C23 N1 C27 117.7(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
C6 C1 C2 C3 1.9(3) . . . . ?
C15 C1 C2 C3 -175.3(2) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C1 C2 C3 C7 -178.4(2) . . . . ?
C2 C3 C4 O1 179.6(2) . . . . ?
C7 C3 C4 O1 -0.9(3) . . . . ?
C2 C3 C4 C5 -4.1(3) . . . . ?
C7 C3 C4 C5 175.3(2) . . . . ?
O1 C4 C5 C6 -179.9(2) . . . . ?
C3 C4 C5 C6 4.0(3) . . . . ?
O1 C4 C5 C11 0.0(4) . . . . ?
C3 C4 C5 C11 -176.0(2) . . . . ?
C2 C1 C6 C5 -2.0(3) . . . . ?
C15 C1 C6 C5 175.3(2) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C11 C5 C6 C1 179.2(2) . . . . ?
C2 C3 C7 C8 -112.2(3) . . . . ?
C4 C3 C7 C8 68.4(3) . . . . ?
C2 C3 C7 C9 126.0(2) . . . . ?
C4 C3 C7 C9 -53.4(3) . . . . ?
C2 C3 C7 C10 8.1(3) . . . . ?
C4 C3 C7 C10 -171.3(3) . . . . ?
C6 C5 C11 C14 -7.6(4) . . . . ?
C4 C5 C11 C14 172.4(3) . . . . ?
C6 C5 C11 C13 111.7(3) . . . . ?
C4 C5 C11 C13 -68.3(3) . . . . ?
C6 C5 C11 C12 -125.6(3) . . . . ?
C4 C5 C11 C12 54.4(4) . . . . ?
C6 C1 C15 C16 137.2(2) . . . . ?
C2 C1 C15 C16 -45.6(3) . . . . ?
C6 C1 C15 C22 -94.2(3) . . . . ?
C2 C1 C15 C22 82.9(3) . . . . ?
C1 C15 C16 C21 110.9(3) . . . . ?
C22 C15 C16 C21 -16.0(3) . . . . ?
C1 C15 C16 C17 -69.9(3) . . . . ?
C22 C15 C16 C17 163.2(2) . . . . ?
C21 C16 C17 C18 -0.9(4) . . . . ?
C15 C16 C17 C18 179.8(3) . . . . ?
C16 C17 C18 C19 0.0(5) . . . . ?
C17 C18 C19 C20 1.4(5) . . . . ?
C18 C19 C20 C21 -1.8(5) . . . . ?
C17 C16 C21 C20 0.5(4) . . . . ?
C15 C16 C21 C20 179.7(3) . . . . ?
C19 C20 C21 C16 0.9(5) . . . . ?
C16 C15 C22 C23 -172.12(19) . . . . ?
C1 C15 C22 C23 59.9(3) . . . . ?
C15 C22 C23 N1 65.9(3) . . . . ?
C15 C22 C23 C24 -113.1(3) . . . . ?
N1 C23 C24 C25 -0.2(5) . . . . ?
C22 C23 C24 C25 178.8(3) . . . . ?
C23 C24 C25 C26 1.2(6) . . . . ?
C24 C25 C26 C27 -2.1(7) . . . . ?
C25 C26 C27 N1 2.3(7) . . . . ?
C24 C23 N1 C27 0.3(5) . . . . ?
C22 C23 N1 C27 -178.8(3) . . . . ?
C26 C27 N1 C23 -1.3(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.82 2.18 2.841(3) 137.8 4_565 yes

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.036

