# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_sm_out
_database_code_depnum_ccdc_archive 'CCDC 1887326'
loop_
_audit_author_name
_audit_author_address
'Dhiraj Das'
;IISER Mohali
India
;
_audit_update_record             
;
2018-12-26 deposited with the CCDC.	2019-07-23 downloaded from the CCDC.
;
_audit_creation_date             2018-10-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H33 N3 O4'
_chemical_formula_sum            'C31 H33 N3 O4'
_chemical_formula_weight         511.60
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.899(2)
_cell_length_b                   11.547(3)
_cell_length_c                   13.186(3)
_cell_angle_alpha                111.235(17)
_cell_angle_beta                 91.111(16)
_cell_angle_gamma                102.013(16)
_cell_volume                     1366.8(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15844
_cell_measurement_temperature    296.0(2)
_cell_measurement_theta_max      24.997
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1624
_diffrn_reflns_av_unetI/netI     0.1749
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15844
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.727
_diffrn_ambient_temperature      296.0(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_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                2059
_reflns_number_total             4803
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.148
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4803
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1856
_refine_ls_R_factor_gt           0.0645
_refine_ls_restrained_S_all      0.938
_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)+(0.0360P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.1136
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C16(H16a,H16b), C25(H25a,H25b), C26(H26a,H26b)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C24(H24), N3(H3)
2.c Idealised Me refined as rotating group:
 C31(H31a,H31b,H31c), C29(H29a,H29b,H29c), C30(H30a,H30b,H30c)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
C31 C 0.8652(5) -0.7280(4) -0.0880(3) 0.1197(17) Uani 1 1 d . . . . .
H31A H 0.8397 -0.6591 -0.1022 0.180 Uiso 1 1 calc GR . . . .
H31B H 0.8465 -0.8030 -0.1539 0.180 Uiso 1 1 calc GR . . . .
H31C H 0.9624 -0.7047 -0.0632 0.180 Uiso 1 1 calc GR . . . .
C1 C 0.5282(3) -0.1898(3) 0.3733(2) 0.0387(7) Uani 1 1 d . . . . .
C2 C 0.6239(3) -0.0900(3) 0.3385(2) 0.0383(7) Uani 1 1 d . . . . .
C3 C 0.6577(3) -0.1706(3) 0.2289(2) 0.0390(7) Uani 1 1 d . . . . .
C4 C 0.7334(3) -0.1371(3) 0.1538(3) 0.0555(9) Uani 1 1 d . . . . .
H4 H 0.7681 -0.0518 0.1646 0.067 Uiso 1 1 calc R . . . .
C5 C 0.7570(3) -0.2346(4) 0.0608(3) 0.0705(11) Uani 1 1 d . . . . .
H5 H 0.8070 -0.2142 0.0082 0.085 Uiso 1 1 calc R . . . .
C6 C 0.7069(4) -0.3608(4) 0.0462(3) 0.0702(11) Uani 1 1 d . . . . .
H6 H 0.7259 -0.4244 -0.0153 0.084 Uiso 1 1 calc R . . . .
C7 C 0.6291(3) -0.3950(3) 0.1210(3) 0.0570(9) Uani 1 1 d . . . . .
H7 H 0.5949 -0.4802 0.1109 0.068 Uiso 1 1 calc R . . . .
C8 C 0.6041(3) -0.2978(3) 0.2110(2) 0.0396(7) Uani 1 1 d . . . . .
C9 C 0.4406(3) -0.4254(2) 0.2992(2) 0.0499(9) Uani 1 1 d . . . . .
H9A H 0.3873 -0.4732 0.2284 0.060 Uiso 1 1 calc R . . . .
H9B H 0.3754 -0.4043 0.3532 0.060 Uiso 1 1 calc R . . . .
C10 C 0.5219(3) -0.5090(3) 0.3254(2) 0.0435(8) Uani 1 1 d . . . . .
C11 C 0.4925(3) -0.6380(3) 0.2660(3) 0.0638(10) Uani 1 1 d . . . . .
H11 H 0.4257 -0.6729 0.2059 0.077 Uiso 1 1 calc R . . . .
C12 C 0.5600(4) -0.7163(3) 0.2938(3) 0.0782(12) Uani 1 1 d . . . . .
H12 H 0.5388 -0.8036 0.2529 0.094 Uiso 1 1 calc R . . . .
C13 C 0.6575(4) -0.6658(4) 0.3809(3) 0.0766(12) Uani 1 1 d . . . . .
H13 H 0.7027 -0.7188 0.4005 0.092 Uiso 1 1 calc R . . . .
C14 C 0.6900(3) -0.5370(4) 0.4405(3) 0.0733(11) Uani 1 1 d . . . . .
H14 H 0.7582 -0.5026 0.4997 0.088 Uiso 1 1 calc R . . . .
C15 C 0.6221(3) -0.4588(3) 0.4128(2) 0.0566(9) Uani 1 1 d . . . . .
H15 H 0.6441 -0.3714 0.4535 0.068 Uiso 1 1 calc R . . . .
C16 C 0.7537(3) -0.0207(2) 0.4209(2) 0.0454(8) Uani 1 1 d . . . . .
H16A H 0.8146 0.0368 0.3941 0.054 Uiso 1 1 calc R . . . .
H16B H 0.7258 0.0307 0.4898 0.054 Uiso 1 1 calc R . . . .
C17 C 0.8397(3) -0.1275(3) 0.5363(2) 0.0413(8) Uani 1 1 d . . . . .
C18 C 0.7745(3) -0.0852(3) 0.6297(3) 0.0569(9) Uani 1 1 d . . . . .
H18 H 0.7118 -0.0338 0.6355 0.068 Uiso 1 1 calc R . . . .
C19 C 0.8057(4) -0.1221(3) 0.7139(3) 0.0698(11) Uani 1 1 d . . . . .
H19 H 0.7640 -0.0947 0.7783 0.084 Uiso 1 1 calc R . . . .
C20 C 0.8986(4) -0.1997(3) 0.7041(3) 0.0690(11) Uani 1 1 d . . . . .
H20 H 0.9177 -0.2234 0.7622 0.083 Uiso 1 1 calc R . . . .
C21 C 0.9624(3) -0.2418(3) 0.6120(3) 0.0551(9) Uani 1 1 d . . . . .
H21 H 1.0245 -0.2934 0.6071 0.066 Uiso 1 1 calc R . . . .
C22 C 0.9335(3) -0.2067(3) 0.5245(2) 0.0402(8) Uani 1 1 d . . . . .
C23 C 0.9838(3) -0.2290(3) 0.4197(2) 0.0422(8) Uani 1 1 d . . . . .
C24 C 0.9193(3) -0.1665(3) 0.3728(2) 0.0454(8) Uani 1 1 d . . . . .
H24 H 0.9329 -0.1648 0.3037 0.054 Uiso 1 1 calc R . . . .
C25 C 1.0872(3) -0.3060(3) 0.3719(2) 0.0519(9) Uani 1 1 d . . . . .
H25A H 1.1686 -0.2771 0.4245 0.062 Uiso 1 1 calc R . . . .
H25B H 1.1160 -0.2897 0.3075 0.062 Uiso 1 1 calc R . . . .
C26 C 1.0350(3) -0.4478(3) 0.3403(2) 0.0614(10) Uani 1 1 d . . . . .
H26A H 1.1112 -0.4888 0.3172 0.074 Uiso 1 1 calc R . . . .
H26B H 1.0046 -0.4642 0.4043 0.074 Uiso 1 1 calc R . . . .
C27 C 0.9309(4) -0.5940(3) 0.1578(3) 0.0560(9) Uani 1 1 d . . . . .
C28 C 0.7827(4) -0.7547(4) -0.0016(3) 0.0706(11) Uani 1 1 d . . . . .
C29 C 0.8150(5) -0.8642(3) 0.0233(3) 0.1193(17) Uani 1 1 d . . . . .
H29A H 0.9135 -0.8572 0.0270 0.179 Uiso 1 1 calc GR . . . .
H29B H 0.7692 -0.9436 -0.0334 0.179 Uiso 1 1 calc GR . . . .
H29C H 0.7830 -0.8617 0.0922 0.179 Uiso 1 1 calc GR . . . .
C30 C 0.6294(4) -0.7801(4) -0.0324(3) 0.142(2) Uani 1 1 d . . . . .
H30A H 0.5797 -0.7925 0.0260 0.213 Uiso 1 1 calc GR . . . .
H30B H 0.6018 -0.8555 -0.0977 0.213 Uiso 1 1 calc GR . . . .
H30C H 0.6089 -0.7087 -0.0454 0.213 Uiso 1 1 calc GR . . . .
N1 N 0.5259(2) -0.3073(2) 0.29702(19) 0.0400(6) Uani 1 1 d . . . . .
N2 N 0.8304(2) -0.1053(2) 0.44060(19) 0.0423(6) Uani 1 1 d . . . . .
N3 N 0.9222(3) -0.5046(2) 0.2542(2) 0.0714(9) Uani 1 1 d . . . . .
H3 H 0.8459 -0.4797 0.2653 0.086 Uiso 1 1 calc R . . . .
O1 O 0.4650(2) -0.16811(18) 0.45413(17) 0.0527(6) Uani 1 1 d . . . . .
O2 O 0.5528(2) 0.00187(18) 0.33152(15) 0.0513(6) Uani 1 1 d . . . . .
H2 H 0.5398 0.0468 0.3931 0.077 Uiso 1 1 calc GR . . . .
O3 O 1.0359(2) -0.6276(2) 0.13008(18) 0.0831(8) Uani 1 1 d . . . . .
O4 O 0.8062(2) -0.6405(2) 0.09928(17) 0.0704(7) Uani 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
C31 C28 1.499(5) . ?
C1 C2 1.543(4) . ?
C1 N1 1.360(3) . ?
C1 O1 1.220(3) . ?
C2 C3 1.497(3) . ?
C2 C16 1.537(3) . ?
C2 O2 1.417(3) . ?
C3 C4 1.369(4) . ?
C3 C8 1.384(3) . ?
C4 C5 1.395(4) . ?
C5 C6 1.379(4) . ?
C6 C7 1.380(4) . ?
C7 C8 1.376(4) . ?
C8 N1 1.409(3) . ?
C9 C10 1.501(3) . ?
C9 N1 1.457(3) . ?
C10 C11 1.372(4) . ?
C10 C15 1.371(4) . ?
C11 C12 1.371(4) . ?
C12 C13 1.353(4) . ?
C13 C14 1.370(4) . ?
C14 C15 1.373(4) . ?
C16 N2 1.443(3) . ?
C17 C18 1.378(4) . ?
C17 C22 1.406(4) . ?
C17 N2 1.381(3) . ?
C18 C19 1.377(4) . ?
C19 C20 1.389(4) . ?
C20 C21 1.357(4) . ?
C21 C22 1.396(4) . ?
C22 C23 1.430(4) . ?
C23 C24 1.346(3) . ?
C23 C25 1.495(4) . ?
C24 N2 1.381(3) . ?
C25 C26 1.505(4) . ?
C26 N3 1.440(3) . ?
C27 N3 1.334(4) . ?
C27 O3 1.202(3) . ?
C27 O4 1.340(3) . ?
C28 C29 1.508(4) . ?
C28 C30 1.502(4) . ?
C28 O4 1.467(3) . ?

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
N1 C1 C2 107.7(3) . . ?
O1 C1 C2 126.5(3) . . ?
O1 C1 N1 125.8(3) . . ?
C3 C2 C1 102.2(2) . . ?
C3 C2 C16 112.4(2) . . ?
C16 C2 C1 110.9(2) . . ?
O2 C2 C1 110.6(2) . . ?
O2 C2 C3 112.0(2) . . ?
O2 C2 C16 108.6(2) . . ?
C4 C3 C2 130.7(3) . . ?
C4 C3 C8 120.5(3) . . ?
C8 C3 C2 108.8(3) . . ?
C3 C4 C5 118.1(3) . . ?
C6 C5 C4 120.6(3) . . ?
C5 C6 C7 121.5(3) . . ?
C8 C7 C6 117.2(3) . . ?
C3 C8 N1 109.8(3) . . ?
C7 C8 C3 122.1(3) . . ?
C7 C8 N1 128.2(3) . . ?
N1 C9 C10 114.0(2) . . ?
C11 C10 C9 120.7(3) . . ?
C15 C10 C9 120.5(3) . . ?
C15 C10 C11 118.8(3) . . ?
C12 C11 C10 121.1(3) . . ?
C13 C12 C11 119.6(4) . . ?
C12 C13 C14 120.3(4) . . ?
C13 C14 C15 120.0(3) . . ?
C10 C15 C14 120.2(3) . . ?
N2 C16 C2 113.9(2) . . ?
C18 C17 C22 122.6(3) . . ?
C18 C17 N2 130.3(3) . . ?
N2 C17 C22 107.2(3) . . ?
C19 C18 C17 117.4(3) . . ?
C18 C19 C20 120.9(4) . . ?
C21 C20 C19 121.7(3) . . ?
C20 C21 C22 119.2(3) . . ?
C17 C22 C23 107.7(3) . . ?
C21 C22 C17 118.2(3) . . ?
C21 C22 C23 134.0(3) . . ?
C22 C23 C25 127.0(3) . . ?
C24 C23 C22 106.1(3) . . ?
C24 C23 C25 126.8(3) . . ?
C23 C24 N2 111.1(3) . . ?
C23 C25 C26 114.6(2) . . ?
N3 C26 C25 114.0(3) . . ?
N3 C27 O4 109.9(3) . . ?
O3 C27 N3 124.0(3) . . ?
O3 C27 O4 126.1(3) . . ?
C31 C28 C29 112.5(4) . . ?
C31 C28 C30 111.4(3) . . ?
C30 C28 C29 109.8(4) . . ?
O4 C28 C31 110.7(3) . . ?
O4 C28 C29 109.5(3) . . ?
O4 C28 C30 102.4(3) . . ?
C1 N1 C8 111.1(2) . . ?
C1 N1 C9 123.6(3) . . ?
C8 N1 C9 125.0(2) . . ?
C17 N2 C16 125.6(3) . . ?
C17 N2 C24 107.9(2) . . ?
C24 N2 C16 126.2(3) . . ?
C27 N3 C26 122.9(3) . . ?
C27 O4 C28 120.4(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
C31 C28 O4 C27 -66.9(4) . . . . ?
C1 C2 C3 C4 176.6(3) . . . . ?
C1 C2 C3 C8 -6.6(3) . . . . ?
C1 C2 C16 N2 54.5(3) . . . . ?
C2 C1 N1 C8 -3.1(3) . . . . ?
C2 C1 N1 C9 -176.7(2) . . . . ?
C2 C3 C4 C5 175.2(3) . . . . ?
C2 C3 C8 C7 -174.3(2) . . . . ?
C2 C3 C8 N1 5.3(3) . . . . ?
C2 C16 N2 C17 -110.0(3) . . . . ?
C2 C16 N2 C24 77.8(3) . . . . ?
C3 C2 C16 N2 -59.3(3) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C3 C8 N1 C1 -1.3(3) . . . . ?
C3 C8 N1 C9 172.2(2) . . . . ?
C4 C3 C8 C7 2.9(4) . . . . ?
C4 C3 C8 N1 -177.5(2) . . . . ?
C4 C5 C6 C7 1.8(5) . . . . ?
C5 C6 C7 C8 -0.3(5) . . . . ?
C6 C7 C8 C3 -2.0(4) . . . . ?
C6 C7 C8 N1 178.5(3) . . . . ?
C7 C8 N1 C1 178.2(3) . . . . ?
C7 C8 N1 C9 -8.3(4) . . . . ?
C8 C3 C4 C5 -1.3(4) . . . . ?
C9 C10 C11 C12 -175.7(3) . . . . ?
C9 C10 C15 C14 175.9(3) . . . . ?
C10 C9 N1 C1 -110.4(3) . . . . ?
C10 C9 N1 C8 76.9(3) . . . . ?
C10 C11 C12 C13 -0.2(5) . . . . ?
C11 C10 C15 C14 -0.8(5) . . . . ?
C11 C12 C13 C14 -0.8(6) . . . . ?
C12 C13 C14 C15 1.0(6) . . . . ?
C13 C14 C15 C10 -0.2(5) . . . . ?
C15 C10 C11 C12 1.0(5) . . . . ?
C16 C2 C3 C4 -64.5(4) . . . . ?
C16 C2 C3 C8 112.3(3) . . . . ?
C17 C18 C19 C20 -0.5(5) . . . . ?
C17 C22 C23 C24 -1.0(3) . . . . ?
C17 C22 C23 C25 179.0(2) . . . . ?
C18 C17 C22 C21 -1.0(4) . . . . ?
C18 C17 C22 C23 -178.5(2) . . . . ?
C18 C17 N2 C16 5.2(5) . . . . ?
C18 C17 N2 C24 178.5(3) . . . . ?
C18 C19 C20 C21 0.2(5) . . . . ?
C19 C20 C21 C22 -0.2(5) . . . . ?
C20 C21 C22 C17 0.6(4) . . . . ?
C20 C21 C22 C23 177.3(3) . . . . ?
C21 C22 C23 C24 -178.0(3) . . . . ?
C21 C22 C23 C25 2.0(5) . . . . ?
C22 C17 C18 C19 0.9(4) . . . . ?
C22 C17 N2 C16 -174.9(2) . . . . ?
C22 C17 N2 C24 -1.6(3) . . . . ?
C22 C23 C24 N2 0.0(3) . . . . ?
C22 C23 C25 C26 70.3(4) . . . . ?
C23 C24 N2 C16 174.3(2) . . . . ?
C23 C24 N2 C17 1.0(3) . . . . ?
C23 C25 C26 N3 64.2(4) . . . . ?
C24 C23 C25 C26 -109.7(3) . . . . ?
C25 C23 C24 N2 180.0(2) . . . . ?
C25 C26 N3 C27 118.3(3) . . . . ?
C29 C28 O4 C27 57.7(4) . . . . ?
C30 C28 O4 C27 174.2(3) . . . . ?
N1 C1 C2 C3 5.8(3) . . . . ?
N1 C1 C2 C16 -114.2(3) . . . . ?
N1 C1 C2 O2 125.2(2) . . . . ?
N1 C9 C10 C11 -135.0(3) . . . . ?
N1 C9 C10 C15 48.4(4) . . . . ?
N2 C17 C18 C19 -179.3(3) . . . . ?
N2 C17 C22 C21 179.2(2) . . . . ?
N2 C17 C22 C23 1.6(3) . . . . ?
N3 C27 O4 C28 -169.6(3) . . . . ?
O1 C1 C2 C3 -173.8(3) . . . . ?
O1 C1 C2 C16 66.1(4) . . . . ?
O1 C1 C2 O2 -54.4(4) . . . . ?
O1 C1 N1 C8 176.6(3) . . . . ?
O1 C1 N1 C9 3.0(4) . . . . ?
O2 C2 C3 C4 58.2(4) . . . . ?
O2 C2 C3 C8 -125.0(2) . . . . ?
O2 C2 C16 N2 176.2(2) . . . . ?
O3 C27 N3 C26 -6.8(5) . . . . ?
O3 C27 O4 C28 9.4(5) . . . . ?
O4 C27 N3 C26 172.3(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_4out
_database_code_depnum_ccdc_archive 'CCDC 1887327'
loop_
_audit_author_name
_audit_author_address
'Dhiraj Das'
;IISER Mohali
India
;
_audit_update_record             
;
2018-12-26 deposited with the CCDC.	2019-07-23 downloaded from the CCDC.
;
_audit_creation_date             2018-10-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H19 Br2 N3 O5'
_chemical_formula_sum            'C25 H19 Br2 N3 O5'
_chemical_formula_weight         601.25
_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'
Br Br -0.2901 2.4595 '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                   11.2334(8)
_cell_length_b                   9.4327(6)
_cell_length_c                   23.5205(18)
_cell_angle_alpha                90
_cell_angle_beta                 92.00(5)
_cell_angle_gamma                90
_cell_volume                     2490.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    29728
_cell_measurement_temperature    296.0(2)
_cell_measurement_theta_max      25.000
_cell_measurement_theta_min      1.733
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.296
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1300
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            29728
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.733
_diffrn_ambient_temperature      296.0(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2699
_reflns_number_total             4386
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4386
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      0.972
_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)+(0.0778P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1582
_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:
 C8(H8a,H8b), C18(H18a,H18b), C19(H19a,H19b)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C11(H11), C13(H13), C14(H14), C21(H21),
 C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c)
;
_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
C1 C -0.0241(5) 0.7757(6) 0.0277(3) 0.0653(16) Uani 1 1 d . . . . .
H1 H -0.0259 0.7020 0.0015 0.078 Uiso 1 1 calc R . . . .
C2 C -0.1195(5) 0.8695(7) 0.0299(3) 0.0686(17) Uani 1 1 d . . . . .
H2 H -0.1843 0.8601 0.0044 0.082 Uiso 1 1 calc R . . . .
C3 C -0.1174(4) 0.9754(6) 0.0695(2) 0.0579(14) Uani 1 1 d . . . . .
C4 C -0.0248(5) 0.9925(6) 0.1066(2) 0.0663(15) Uani 1 1 d . . . . .
H4 H -0.0246 1.0640 0.1339 0.080 Uiso 1 1 calc R . . . .
C5 C 0.0702(5) 0.9000(6) 0.1029(2) 0.0626(15) Uani 1 1 d . . . . .
H5 H 0.1359 0.9112 0.1277 0.075 Uiso 1 1 calc R . . . .
C6 C 0.0708(4) 0.7919(6) 0.0637(2) 0.0532(13) Uani 1 1 d . . . . .
C7 C 0.1739(5) 0.6958(6) 0.0581(2) 0.0565(14) Uani 1 1 d . . . . .
C8 C 0.3743(4) 0.6576(5) 0.0852(2) 0.0476(12) Uani 1 1 d . . . . .
H8A H 0.3984 0.6775 0.0468 0.057 Uiso 1 1 calc R . . . .
H8B H 0.3726 0.5557 0.0907 0.057 Uiso 1 1 calc R . . . .
C9 C 0.4575(4) 0.7277(5) 0.1285(2) 0.0405(11) Uani 1 1 d . . . . .
C10 C 0.4319(4) 0.8851(5) 0.1317(2) 0.0422(11) Uani 1 1 d . . . . .
C11 C 0.4413(4) 0.9865(5) 0.0901(2) 0.0468(12) Uani 1 1 d . . . . .
H11 H 0.4731 0.9662 0.0551 0.056 Uiso 1 1 calc R . . . .
C12 C 0.4005(4) 1.1214(5) 0.1035(2) 0.0485(12) Uani 1 1 d . . . . .
C13 C 0.3557(4) 1.1560(6) 0.1560(2) 0.0592(15) Uani 1 1 d . . . . .
H13 H 0.3318 1.2484 0.1634 0.071 Uiso 1 1 calc R . . . .
C14 C 0.3466(4) 1.0522(5) 0.1976(2) 0.0562(14) Uani 1 1 d . . . . .
H14 H 0.3163 1.0732 0.2329 0.067 Uiso 1 1 calc R . . . .
C15 C 0.3841(4) 0.9168(5) 0.1847(2) 0.0465(12) Uani 1 1 d . . . . .
C16 C 0.3477(5) 0.7902(6) 0.2779(2) 0.0634(15) Uani 1 1 d . . . . .
H16A H 0.3376 0.6935 0.2896 0.095 Uiso 1 1 calc GR . . . .
H16B H 0.2743 0.8407 0.2819 0.095 Uiso 1 1 calc GR . . . .
H16C H 0.4091 0.8337 0.3014 0.095 Uiso 1 1 calc GR . . . .
C17 C 0.4219(4) 0.6796(5) 0.1894(2) 0.0478(12) Uani 1 1 d . . . . .
C18 C 0.6082(4) 0.5488(5) 0.0930(2) 0.0504(12) Uani 1 1 d . . . . .
H18A H 0.5801 0.5377 0.0538 0.061 Uiso 1 1 calc R . . . .
H18B H 0.5708 0.4773 0.1160 0.061 Uiso 1 1 calc R . . . .
C19 C 0.7416(4) 0.5361(5) 0.0977(2) 0.0568(13) Uani 1 1 d . . . . .
H19A H 0.7662 0.4406 0.1079 0.068 Uiso 1 1 calc R . . . .
H19B H 0.7782 0.5633 0.0626 0.068 Uiso 1 1 calc R . . . .
C20 C 0.7703(4) 0.6376(5) 0.1440(2) 0.0488(12) Uani 1 1 d . . . . .
C21 C 0.8731(4) 0.6544(6) 0.1755(2) 0.0589(14) Uani 1 1 d . . . . .
H21 H 0.9384 0.5956 0.1704 0.071 Uiso 1 1 calc R . . . .
C22 C 0.8769(5) 0.7616(6) 0.2152(3) 0.0585(15) Uani 1 1 d . . . . .
C23 C 0.7833(4) 0.8531(6) 0.2232(2) 0.0553(13) Uani 1 1 d . . . . .
H23 H 0.7903 0.9250 0.2502 0.066 Uiso 1 1 calc R . . . .
C24 C 0.6809(4) 0.8375(5) 0.1916(2) 0.0501(12) Uani 1 1 d . . . . .
H24 H 0.6167 0.8981 0.1964 0.060 Uiso 1 1 calc R . . . .
C25 C 0.6742(4) 0.7294(5) 0.1518(2) 0.0438(11) Uani 1 1 d . . . . .
Br1 Br 0.40473(6) 1.26190(6) 0.04500(3) 0.0685(2) Uani 1 1 d . . . . .
Br2 Br 1.01680(6) 0.78140(9) 0.26082(4) 0.1017(3) Uani 1 1 d . . . . .
N1 N 0.3817(4) 0.7940(5) 0.21855(18) 0.0498(10) Uani 1 1 d . . . . .
N2 N 0.5811(3) 0.6931(4) 0.11402(17) 0.0444(10) Uani 1 1 d . . . . .
N3 N -0.2198(5) 1.0758(6) 0.0710(3) 0.0814(16) Uani 1 1 d . . . . .
O1 O 0.4292(3) 0.5586(4) 0.20732(16) 0.0630(10) Uani 1 1 d . . . . .
O2 O 0.2583(3) 0.7204(4) 0.09559(15) 0.0541(9) Uani 1 1 d . . . . .
O3 O 0.1827(4) 0.6056(5) 0.0225(2) 0.1031(18) Uani 1 1 d . . . . .
O4 O -0.2208(5) 1.1587(7) 0.1101(2) 0.1151(19) Uani 1 1 d . . . . .
O5 O -0.2914(4) 1.0726(6) 0.0352(3) 0.116(2) Uani 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
C1 H1 0.9300 . ?
C1 C2 1.392(8) . ?
C1 C6 1.346(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.365(8) . ?
C3 C4 1.345(7) . ?
C3 N3 1.492(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(7) . ?
C6 C7 1.480(7) . ?
C7 O2 1.293(6) . ?
C7 O3 1.200(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.511(6) . ?
C8 O2 1.460(5) . ?
C9 C10 1.514(6) . ?
C9 C17 1.567(7) . ?
C9 N2 1.478(6) . ?
C10 C11 1.373(6) . ?
C10 C15 1.408(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(6) . ?
C12 C13 1.388(7) . ?
C12 Br1 1.913(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.390(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(6) . ?
C15 N1 1.406(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 N1 1.461(6) . ?
C17 N1 1.364(6) . ?
C17 O1 1.219(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.504(7) . ?
C18 N2 1.483(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.476(7) . ?
C20 C21 1.359(6) . ?
C20 C25 1.401(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.377(7) . ?
C22 C23 1.378(7) . ?
C22 Br2 1.881(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.357(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.384(6) . ?
C25 N2 1.391(5) . ?
N3 O4 1.207(7) . ?
N3 O5 1.144(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
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C6 C1 C2 119.9(6) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(5) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 N3 119.1(5) . . ?
C4 C3 C2 121.7(5) . . ?
C4 C3 N3 119.2(6) . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 117.6(6) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 H5 118.9 . . ?
C6 C5 C4 122.1(5) . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C5 118.9(5) . . ?
C1 C6 C7 118.6(5) . . ?
C5 C6 C7 122.4(5) . . ?
O2 C7 C6 112.7(5) . . ?
O3 C7 C6 125.5(5) . . ?
O3 C7 O2 121.8(5) . . ?
H8A C8 H8B 109.0 . . ?
C9 C8 H8A 110.9 . . ?
C9 C8 H8B 110.9 . . ?
O2 C8 H8A 110.9 . . ?
O2 C8 H8B 110.9 . . ?
O2 C8 C9 104.1(4) . . ?
C8 C9 C10 110.4(4) . . ?
C8 C9 C17 108.5(4) . . ?
C10 C9 C17 100.6(4) . . ?
N2 C9 C8 108.2(4) . . ?
N2 C9 C10 114.2(4) . . ?
N2 C9 C17 114.7(4) . . ?
C11 C10 C9 128.9(4) . . ?
C11 C10 C15 121.6(4) . . ?
C15 C10 C9 109.3(4) . . ?
C10 C11 H11 121.9 . . ?
C10 C11 C12 116.2(5) . . ?
C12 C11 H11 121.9 . . ?
C11 C12 Br1 117.0(4) . . ?
C13 C12 C11 123.3(5) . . ?
C13 C12 Br1 119.8(4) . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.9(5) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 121.1 . . ?
C15 C14 C13 117.8(5) . . ?
C15 C14 H14 121.1 . . ?
C14 C15 C10 121.3(5) . . ?
C14 C15 N1 128.7(5) . . ?
N1 C15 C10 110.0(4) . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
N1 C17 C9 109.3(4) . . ?
O1 C17 C9 124.9(5) . . ?
O1 C17 N1 125.8(5) . . ?
H18A C18 H18B 108.8 . . ?
C19 C18 H18A 110.7 . . ?
C19 C18 H18B 110.7 . . ?
N2 C18 H18A 110.7 . . ?
N2 C18 H18B 110.7 . . ?
N2 C18 C19 105.3(4) . . ?
C18 C19 H19A 111.5 . . ?
C18 C19 H19B 111.5 . . ?
H19A C19 H19B 109.3 . . ?
C20 C19 C18 101.2(4) . . ?
C20 C19 H19A 111.5 . . ?
C20 C19 H19B 111.5 . . ?
C21 C20 C19 129.6(5) . . ?
C21 C20 C25 120.0(5) . . ?
C25 C20 C19 110.4(4) . . ?
C20 C21 H21 121.3 . . ?
C20 C21 C22 117.4(5) . . ?
C22 C21 H21 121.3 . . ?
C21 C22 C23 123.2(5) . . ?
C21 C22 Br2 117.7(4) . . ?
C23 C22 Br2 119.1(4) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.6(5) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 120.8 . . ?
C23 C24 C25 118.4(5) . . ?
C25 C24 H24 120.8 . . ?
C24 C25 C20 121.4(4) . . ?
C24 C25 N2 129.4(4) . . ?
N2 C25 C20 109.2(4) . . ?
C15 N1 C16 124.9(4) . . ?
C17 N1 C15 110.7(4) . . ?
C17 N1 C16 124.3(4) . . ?
C9 N2 C18 119.0(4) . . ?
C25 N2 C9 119.3(4) . . ?
C25 N2 C18 106.3(3) . . ?
O4 N3 C3 117.2(6) . . ?
O5 N3 C3 119.2(6) . . ?
O5 N3 O4 123.5(7) . . ?
C7 O2 C8 116.8(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
C1 C2 C3 C4 0.4(9) . . . . ?
C1 C2 C3 N3 179.6(5) . . . . ?
C1 C6 C7 O2 -178.9(5) . . . . ?
C1 C6 C7 O3 2.6(10) . . . . ?
C2 C1 C6 C5 1.3(9) . . . . ?
C2 C1 C6 C7 -176.4(5) . . . . ?
C2 C3 C4 C5 1.0(9) . . . . ?
C2 C3 N3 O4 172.6(6) . . . . ?
C2 C3 N3 O5 -8.9(9) . . . . ?
C3 C4 C5 C6 -1.3(9) . . . . ?
C4 C3 N3 O4 -8.2(9) . . . . ?
C4 C3 N3 O5 170.3(6) . . . . ?
C4 C5 C6 C1 0.1(9) . . . . ?
C4 C5 C6 C7 177.7(5) . . . . ?
C5 C6 C7 O2 3.5(8) . . . . ?
C5 C6 C7 O3 -175.0(6) . . . . ?
C6 C1 C2 C3 -1.6(9) . . . . ?
C6 C7 O2 C8 -164.9(4) . . . . ?
C8 C9 C10 C11 -62.9(6) . . . . ?
C8 C9 C10 C15 111.9(4) . . . . ?
C8 C9 C17 N1 -114.6(4) . . . . ?
C8 C9 C17 O1 65.3(6) . . . . ?
C8 C9 N2 C18 -38.6(5) . . . . ?
C8 C9 N2 C25 -171.5(4) . . . . ?
C9 C8 O2 C7 169.1(4) . . . . ?
C9 C10 C11 C12 173.9(4) . . . . ?
C9 C10 C15 C14 -176.4(4) . . . . ?
C9 C10 C15 N1 3.1(5) . . . . ?
C9 C17 N1 C15 0.6(5) . . . . ?
C9 C17 N1 C16 -176.0(4) . . . . ?
C10 C9 C17 N1 1.2(4) . . . . ?
C10 C9 C17 O1 -178.9(4) . . . . ?
C10 C9 N2 C18 -161.9(4) . . . . ?
C10 C9 N2 C25 65.2(5) . . . . ?
C10 C11 C12 C13 1.9(7) . . . . ?
C10 C11 C12 Br1 -176.8(3) . . . . ?
C10 C15 N1 C16 174.3(4) . . . . ?
C10 C15 N1 C17 -2.3(5) . . . . ?
C11 C10 C15 C14 -1.2(7) . . . . ?
C11 C10 C15 N1 178.4(4) . . . . ?
C11 C12 C13 C14 -2.0(7) . . . . ?
C12 C13 C14 C15 0.5(7) . . . . ?
C13 C14 C15 C10 1.0(7) . . . . ?
C13 C14 C15 N1 -178.4(4) . . . . ?
C14 C15 N1 C16 -6.2(8) . . . . ?
C14 C15 N1 C17 177.2(5) . . . . ?
C15 C10 C11 C12 -0.3(6) . . . . ?
C17 C9 C10 C11 -177.4(4) . . . . ?
C17 C9 C10 C15 -2.6(4) . . . . ?
C17 C9 N2 C18 82.7(5) . . . . ?
C17 C9 N2 C25 -50.2(5) . . . . ?
C18 C19 C20 C21 165.6(5) . . . . ?
C18 C19 C20 C25 -17.3(6) . . . . ?
C19 C18 N2 C9 -164.9(4) . . . . ?
C19 C18 N2 C25 -26.7(5) . . . . ?
C19 C20 C21 C22 178.0(5) . . . . ?
C19 C20 C25 C24 -177.8(5) . . . . ?
C19 C20 C25 N2 1.2(6) . . . . ?
C20 C21 C22 C23 -1.5(8) . . . . ?
C20 C21 C22 Br2 177.8(4) . . . . ?
C20 C25 N2 C9 154.1(4) . . . . ?
C20 C25 N2 C18 16.0(5) . . . . ?
C21 C20 C25 C24 -0.4(8) . . . . ?
C21 C20 C25 N2 178.7(4) . . . . ?
C21 C22 C23 C24 1.0(8) . . . . ?
C22 C23 C24 C25 -0.2(8) . . . . ?
C23 C24 C25 C20 -0.1(7) . . . . ?
C23 C24 C25 N2 -179.0(5) . . . . ?
C24 C25 N2 C9 -27.0(7) . . . . ?
C24 C25 N2 C18 -165.1(5) . . . . ?
C25 C20 C21 C22 1.1(8) . . . . ?
Br1 C12 C13 C14 176.6(4) . . . . ?
Br2 C22 C23 C24 -178.3(4) . . . . ?
N2 C9 C10 C11 59.2(6) . . . . ?
N2 C9 C10 C15 -126.0(4) . . . . ?
N2 C9 C17 N1 124.3(4) . . . . ?
N2 C9 C17 O1 -55.8(6) . . . . ?
N2 C18 C19 C20 26.0(5) . . . . ?
N3 C3 C4 C5 -178.2(5) . . . . ?
O1 C17 N1 C15 -179.4(5) . . . . ?
O1 C17 N1 C16 4.0(7) . . . . ?
O2 C8 C9 C10 -43.2(5) . . . . ?
O2 C8 C9 C17 66.2(4) . . . . ?
O2 C8 C9 N2 -168.8(3) . . . . ?
O3 C7 O2 C8 13.7(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
