# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_rn142_0m_a_a_a
_database_code_depnum_ccdc_archive 'CCDC 1973061'
loop_
_audit_author_name
_audit_author_address
'AMALA RASAMSETTY'
;IIT Bombay
India
;
_audit_update_record             
;
2019-12-19 deposited with the CCDC.	2020-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H27 Cl0 N3 O3'
_chemical_formula_sum            'C25 H27 Cl0 N3 O3'
_chemical_formula_weight         417.50

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2512(12)
_cell_length_b                   10.4301(14)
_cell_length_c                   15.810(2)
_cell_angle_alpha                80.059(6)
_cell_angle_beta                 79.541(6)
_cell_angle_gamma                87.359(6)
_cell_volume                     1317.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    2882
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      19.63

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.052
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25836
_diffrn_reflns_av_R_equivalents  0.1707
_diffrn_reflns_av_sigmaI/netI    0.1603
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4659
_reflns_number_gt                1995
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4659
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2127
_refine_ls_R_factor_gt           0.0916
_refine_ls_wR_factor_ref         0.3220
_refine_ls_wR_factor_gt          0.2604
_refine_ls_goodness_of_fit_ref   0.884
_refine_ls_restrained_S_all      0.884
_refine_ls_shift/su_max          0.079
_refine_ls_shift/su_mean         0.015

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1244(4) 0.4326(4) 0.7021(2) 0.0563(11) Uani 1 1 d . . .
O3 O 0.4603(5) 0.1705(4) 0.4969(2) 0.0575(11) Uani 1 1 d . . .
O2 O 0.1343(4) 0.3252(4) 0.8384(3) 0.0610(12) Uani 1 1 d . . .
N2 N 0.3221(5) 0.4719(4) 0.7757(3) 0.0405(11) Uani 1 1 d . . .
N1 N 0.4576(5) 0.8104(4) 0.6922(3) 0.0478(12) Uani 1 1 d . . .
H1N H 0.4786 0.8270 0.6361 0.057 Uiso 1 1 calc R . .
N3 N 0.8354(6) 0.4922(5) 0.6200(3) 0.0598(14) Uani 1 1 d . . .
H3N H 0.9397 0.5029 0.6143 0.072 Uiso 1 1 calc R . .
C21 C 0.4813(6) 0.3454(5) 0.5772(3) 0.0384(13) Uani 1 1 d . . .
H21 H 0.3675 0.3558 0.5911 0.046 Uiso 1 1 calc R . .
C20 C 0.5891(6) 0.4222(5) 0.6071(3) 0.0377(13) Uani 1 1 d . . .
C5 C 0.4607(6) 0.8985(5) 0.7472(3) 0.0426(14) Uani 1 1 d . . .
C8 C 0.4145(6) 0.6891(5) 0.7429(3) 0.0387(13) Uani 1 1 d . . .
C9 C 0.4025(6) 0.5707(5) 0.7025(3) 0.0427(14) Uani 1 1 d . . .
H9 H 0.3296 0.5910 0.6593 0.051 Uiso 1 1 calc R . .
C12 C 0.1857(6) 0.4118(5) 0.7674(4) 0.0414(13) Uani 1 1 d . . .
C17 C 0.5626(6) 0.5214(5) 0.6595(3) 0.0378(13) Uani 1 1 d . . .
C22 C 0.5498(7) 0.2560(5) 0.5274(3) 0.0441(14) Uani 1 1 d . . .
C6 C 0.4212(6) 0.8313(6) 0.8327(4) 0.0531(16) Uani 1 1 d . . .
C7 C 0.3933(6) 0.6970(5) 0.8265(3) 0.0439(14) Uani 1 1 d . . .
C10 C 0.3872(7) 0.4599(5) 0.8558(3) 0.0509(15) Uani 1 1 d . . .
H10A H 0.5055 0.4454 0.8436 0.061 Uiso 1 1 calc R . .
H10B H 0.3388 0.3852 0.8964 0.061 Uiso 1 1 calc R . .
C19 C 0.7623(6) 0.4055(6) 0.5828(3) 0.0468(14) Uani 1 1 d . . .
C18 C 0.7149(7) 0.5590(6) 0.6675(4) 0.0512(15) Uani 1 1 d . . .
H18 H 0.7340 0.6207 0.7004 0.061 Uiso 1 1 calc R . .
C11 C 0.3499(7) 0.5818(5) 0.8972(4) 0.0576(17) Uani 1 1 d . . .
H11A H 0.4146 0.5812 0.9428 0.069 Uiso 1 1 calc R . .
H11B H 0.2341 0.5857 0.9229 0.069 Uiso 1 1 calc R . .
C23 C 0.7218(8) 0.2398(6) 0.5056(4) 0.0572(16) Uani 1 1 d . . .
H23 H 0.7637 0.1749 0.4737 0.069 Uiso 1 1 calc R . .
C4 C 0.4986(7) 1.0288(6) 0.7280(4) 0.0583(16) Uani 1 1 d . . .
H4 H 0.5253 1.0709 0.6705 0.070 Uiso 1 1 calc R . .
C13 C -0.0086(7) 0.2393(6) 0.8439(4) 0.0651(19) Uani 1 1 d . . .
C24 C 0.8262(7) 0.3145(6) 0.5293(4) 0.0587(17) Uani 1 1 d . . .
H24 H 0.9392 0.3065 0.5107 0.070 Uiso 1 1 calc R . .
C1 C 0.4193(7) 0.9000(7) 0.9014(4) 0.0631(18) Uani 1 1 d . . .
H1 H 0.3939 0.8582 0.9590 0.076 Uiso 1 1 calc R . .
C2 C 0.4556(8) 1.0306(7) 0.8826(5) 0.0710(19) Uani 1 1 d . . .
H2 H 0.4537 1.0777 0.9276 0.085 Uiso 1 1 calc R . .
C3 C 0.4957(8) 1.0930(6) 0.7947(5) 0.0707(19) Uani 1 1 d . . .
H3 H 0.5207 1.1810 0.7829 0.085 Uiso 1 1 calc R . .
C25 C 0.2856(8) 0.1730(7) 0.5223(4) 0.075(2) Uani 1 1 d . . .
H25A H 0.2383 0.1095 0.4971 0.113 Uiso 1 1 calc R . .
H25B H 0.2434 0.2579 0.5023 0.113 Uiso 1 1 calc R . .
H25C H 0.2574 0.1532 0.5848 0.113 Uiso 1 1 calc R . .
C15 C -0.1644(7) 0.3264(6) 0.8477(5) 0.080(2) Uani 1 1 d . . .
H15A H -0.1713 0.3748 0.8947 0.119 Uiso 1 1 calc R . .
H15B H -0.2600 0.2732 0.8572 0.119 Uiso 1 1 calc R . .
H15C H -0.1593 0.3857 0.7936 0.119 Uiso 1 1 calc R . .
C14 C -0.0044(9) 0.1547(7) 0.9314(5) 0.100(3) Uani 1 1 d . . .
H14A H -0.0182 0.2083 0.9759 0.151 Uiso 1 1 calc R . .
H14B H 0.0996 0.1091 0.9298 0.151 Uiso 1 1 calc R . .
H14C H -0.0919 0.0930 0.9441 0.151 Uiso 1 1 calc R . .
C16 C 0.0166(10) 0.1627(7) 0.7702(5) 0.104(3) Uani 1 1 d . . .
H16A H 0.0185 0.2211 0.7159 0.156 Uiso 1 1 calc R . .
H16B H -0.0719 0.1026 0.7786 0.156 Uiso 1 1 calc R . .
H16C H 0.1194 0.1154 0.7689 0.156 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C12 1.213(6) . ?
O3 C25 1.425(7) . ?
O3 C22 1.383(6) . ?
O2 C12 1.330(6) . ?
O2 C13 1.495(6) . ?
N2 C12 1.350(6) . ?
N2 C10 1.447(6) . ?
N2 C9 1.489(6) . ?
N1 C5 1.373(6) . ?
N1 C8 1.399(6) . ?
N1 H1N 0.8600 . ?
N3 C18 1.372(7) . ?
N3 C19 1.375(7) . ?
N3 H3N 0.8600 . ?
C21 C22 1.361(7) . ?
C21 C20 1.416(7) . ?
C21 H21 0.9300 . ?
C20 C17 1.418(7) . ?
C20 C19 1.422(7) . ?
C5 C4 1.378(7) . ?
C5 C6 1.400(7) . ?
C8 C7 1.319(7) . ?
C8 C9 1.500(7) . ?
C9 C17 1.484(7) . ?
C9 H9 0.9800 . ?
C17 C18 1.367(7) . ?
C22 C23 1.408(8) . ?
C6 C1 1.398(8) . ?
C6 C7 1.453(7) . ?
C7 C11 1.500(7) . ?
C10 C11 1.523(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C19 C24 1.402(8) . ?
C18 H18 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C23 C24 1.330(8) . ?
C23 H23 0.9300 . ?
C4 C3 1.339(8) . ?
C4 H4 0.9300 . ?
C13 C16 1.503(9) . ?
C13 C14 1.513(8) . ?
C13 C15 1.538(8) . ?
C24 H24 0.9300 . ?
C1 C2 1.378(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.416(8) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C25 O3 C22 117.6(4) . . ?
C12 O2 C13 121.5(4) . . ?
C12 N2 C10 124.5(4) . . ?
C12 N2 C9 119.5(4) . . ?
C10 N2 C9 115.5(4) . . ?
C5 N1 C8 108.4(4) . . ?
C5 N1 H1N 125.8 . . ?
C8 N1 H1N 125.8 . . ?
C18 N3 C19 109.0(5) . . ?
C18 N3 H3N 125.5 . . ?
C19 N3 H3N 125.5 . . ?
C22 C21 C20 117.7(5) . . ?
C22 C21 H21 121.1 . . ?
C20 C21 H21 121.1 . . ?
C17 C20 C19 107.4(5) . . ?
C17 C20 C21 133.2(5) . . ?
C19 C20 C21 119.4(5) . . ?
N1 C5 C4 129.8(5) . . ?
N1 C5 C6 107.4(5) . . ?
C4 C5 C6 122.8(5) . . ?
C7 C8 N1 110.3(5) . . ?
C7 C8 C9 127.9(5) . . ?
N1 C8 C9 121.8(4) . . ?
N2 C9 C8 104.6(4) . . ?
N2 C9 C17 111.3(4) . . ?
C8 C9 C17 114.6(4) . . ?
N2 C9 H9 108.7 . . ?
C8 C9 H9 108.7 . . ?
C17 C9 H9 108.7 . . ?
O1 C12 O2 125.8(5) . . ?
O1 C12 N2 123.4(5) . . ?
O2 C12 N2 110.7(5) . . ?
C18 C17 C20 106.6(5) . . ?
C18 C17 C9 125.7(5) . . ?
C20 C17 C9 127.6(4) . . ?
C21 C22 C23 121.7(5) . . ?
C21 C22 O3 124.2(5) . . ?
C23 C22 O3 114.1(5) . . ?
C5 C6 C1 118.4(5) . . ?
C5 C6 C7 106.7(5) . . ?
C1 C6 C7 134.9(6) . . ?
C8 C7 C6 107.2(5) . . ?
C8 C7 C11 122.7(5) . . ?
C6 C7 C11 130.0(5) . . ?
N2 C10 C11 111.1(4) . . ?
N2 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
N2 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
N3 C19 C20 106.8(5) . . ?
N3 C19 C24 132.7(5) . . ?
C20 C19 C24 120.4(5) . . ?
N3 C18 C17 110.1(5) . . ?
N3 C18 H18 125.0 . . ?
C17 C18 H18 125.0 . . ?
C10 C11 C7 107.5(4) . . ?
C10 C11 H11A 110.2 . . ?
C7 C11 H11A 110.2 . . ?
C10 C11 H11B 110.2 . . ?
C7 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C24 C23 C22 121.9(6) . . ?
C24 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
C3 C4 C5 118.0(6) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C16 C13 O2 111.5(5) . . ?
C16 C13 C14 112.7(6) . . ?
O2 C13 C14 100.0(5) . . ?
C16 C13 C15 113.6(6) . . ?
O2 C13 C15 107.3(5) . . ?
C14 C13 C15 110.7(5) . . ?
C23 C24 C19 118.6(6) . . ?
C23 C24 H24 120.7 . . ?
C19 C24 H24 120.7 . . ?
C2 C1 C6 119.0(6) . . ?
C2 C1 H1 120.5 . . ?
C6 C1 H1 120.5 . . ?
C1 C2 C3 120.0(6) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 121.8(6) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.060

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.088 0.199 0.214 151.8 43.3
2 -0.089 -0.199 0.787 151.7 42.0
_platon_squeeze_details          
;
;
