# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_sn_5_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2324031'
loop_
_audit_author_name
_audit_author_address
'Srinu Tothadi'
;CSIR CSMCRI Bhavnagar 
India
;
_audit_update_record             
;
2024-01-08 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_audit_creation_date             2022-12-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 N2 O5'
_chemical_formula_sum            'C15 H16 N2 O5'
_chemical_formula_weight         304.30
_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                   7.456(6)
_cell_length_b                   8.475(8)
_cell_length_c                   11.895(16)
_cell_angle_alpha                82.16(6)
_cell_angle_beta                 76.38(5)
_cell_angle_gamma                71.47(4)
_cell_volume                     691.1(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2407
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30.90
_cell_measurement_theta_min      3.00
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.7480
_exptl_absorpt_correction_T_min  0.6936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1075 before and 0.0645 after correction. The Ratio of minimum to maximum transmission is 0.9273. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            30947
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.108
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2101
_reflns_number_total             2380
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.067
_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)+(0.0587P)²+0.2122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1113
_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:
 C4(H4), C6(H6), C7(H7), C13(H13)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C12(H12A,H12B,H12C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.68085(17) 0.23765(14) 0.12714(9) 0.0440(3) Uani 1 1 d . . . . .
O2 O 0.16352(19) 0.73204(14) 0.52140(10) 0.0508(4) Uani 1 1 d . . . . .
O3 O -0.1911(2) 0.82737(17) 0.87921(11) 0.0579(4) Uani 1 1 d . . . . .
O4 O 0.0164(2) 0.29278(16) 0.77672(10) 0.0549(4) Uani 1 1 d . . . . .
O5 O 0.58051(17) 0.53663(14) 0.19265(9) 0.0424(3) Uani 1 1 d . . . . .
N1 N -0.09027(18) 0.55937(17) 0.82660(10) 0.0361(3) Uani 1 1 d . . . . .
N2 N -0.00060(18) 0.77442(15) 0.70228(11) 0.0330(3) Uani 1 1 d . . . . .
C1 C -0.1997(3) 0.5089(3) 0.93701(14) 0.0529(5) Uani 1 1 d . . . . .
H1A H -0.324315 0.510167 0.927211 0.079 Uiso 1 1 calc GR . . . .
H1B H -0.215582 0.585080 0.993917 0.079 Uiso 1 1 calc GR . . . .
H1C H -0.131036 0.398395 0.962402 0.079 Uiso 1 1 calc GR . . . .
C2 C 0.0127(2) 0.4373(2) 0.74991(13) 0.0342(4) Uani 1 1 d . . . . .
C3 C 0.1135(2) 0.49202(18) 0.63644(12) 0.0286(3) Uani 1 1 d . . . . .
C4 C 0.2081(2) 0.36575(18) 0.56403(12) 0.0299(3) Uani 1 1 d . . . . .
H4 H 0.188583 0.265608 0.598467 0.036 Uiso 1 1 calc R . . . .
C5 C 0.32904(19) 0.34239(18) 0.45013(12) 0.0280(3) Uani 1 1 d . . . . .
C6 C 0.3874(2) 0.18052(18) 0.41218(13) 0.0336(4) Uani 1 1 d . . . . .
H6 H 0.345951 0.097792 0.460813 0.040 Uiso 1 1 calc R . . . .
C7 C 0.5038(2) 0.14023(19) 0.30556(13) 0.0358(4) Uani 1 1 d . . . . .
H7 H 0.539474 0.032066 0.282594 0.043 Uiso 1 1 calc R . . . .
C8 C 0.5673(2) 0.26147(18) 0.23296(12) 0.0312(3) Uani 1 1 d . . . . .
C9 C 0.7200(3) 0.0809(2) 0.07745(16) 0.0525(5) Uani 1 1 d . . . . .
H9A H 0.794096 -0.007692 0.122485 0.079 Uiso 1 1 calc GR . . . .
H9B H 0.791714 0.085170 -0.000763 0.079 Uiso 1 1 calc GR . . . .
H9C H 0.600205 0.060903 0.077605 0.079 Uiso 1 1 calc GR . . . .
C10 C -0.0997(2) 0.7267(2) 0.80756(13) 0.0369(4) Uani 1 1 d . . . . .
C11 C 0.0981(2) 0.67007(19) 0.61282(12) 0.0311(3) Uani 1 1 d . . . . .
C12 C -0.0155(3) 0.9523(2) 0.68075(16) 0.0473(4) Uani 1 1 d . . . . .
H12A H -0.115731 1.006502 0.638218 0.071 Uiso 1 1 calc GR . . . .
H12B H 0.105302 0.964770 0.636553 0.071 Uiso 1 1 calc GR . . . .
H12C H -0.045942 1.001995 0.753382 0.071 Uiso 1 1 calc GR . . . .
C13 C 0.3942(2) 0.46526(18) 0.37554(12) 0.0300(3) Uani 1 1 d . . . . .
H13 H 0.358151 0.573611 0.398247 0.036 Uiso 1 1 calc R . . . .
C14 C 0.5106(2) 0.42570(18) 0.26977(12) 0.0295(3) Uani 1 1 d . . . . .
C15 C 0.4924(3) 0.7093(2) 0.21173(16) 0.0486(4) Uani 1 1 d . . . . .
H15A H 0.355296 0.736172 0.218523 0.073 Uiso 1 1 calc GR . . . .
H15B H 0.543913 0.775070 0.147656 0.073 Uiso 1 1 calc GR . . . .
H15C H 0.518690 0.732844 0.281869 0.073 Uiso 1 1 calc GR . . . .


_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 C8 1.342(2) . ?
O1 C9 1.445(2) . ?
O2 C11 1.206(2) . ?
O3 C10 1.214(2) . ?
O4 C2 1.216(2) . ?
O5 C14 1.360(2) . ?
O5 C15 1.426(2) . ?
N1 C1 1.462(2) . ?
N1 C2 1.384(2) . ?
N1 C10 1.387(3) . ?
N2 C10 1.376(2) . ?
N2 C11 1.389(2) . ?
N2 C12 1.467(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.474(3) . ?
C3 C4 1.367(2) . ?
C3 C11 1.469(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.439(3) . ?
C5 C6 1.404(2) . ?
C5 C13 1.405(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.375(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.379(2) . ?
C8 C14 1.419(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C14 1.365(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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 O1 C9 118.45(14) . . ?
C14 O5 C15 117.22(14) . . ?
C2 N1 C1 117.62(16) . . ?
C2 N1 C10 125.53(14) . . ?
C10 N1 C1 116.85(15) . . ?
C10 N2 C11 124.96(15) . . ?
C10 N2 C12 116.62(15) . . ?
C11 N2 C12 118.20(15) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O4 C2 N1 120.28(16) . . ?
O4 C2 C3 122.85(16) . . ?
N1 C2 C3 116.87(16) . . ?
C4 C3 C2 113.71(15) . . ?
C4 C3 C11 127.96(15) . . ?
C11 C3 C2 118.30(14) . . ?
C3 C4 H4 110.7 . . ?
C3 C4 C5 138.61(14) . . ?
C5 C4 H4 110.7 . . ?
C6 C5 C4 116.00(14) . . ?
C6 C5 C13 117.95(15) . . ?
C13 C5 C4 126.04(15) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 C5 122.22(15) . . ?
C7 C6 H6 118.9 . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.46(15) . . ?
C8 C7 H7 120.3 . . ?
O1 C8 C7 125.01(15) . . ?
O1 C8 C14 115.75(14) . . ?
C7 C8 C14 119.24(15) . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 N1 122.28(16) . . ?
O3 C10 N2 121.07(18) . . ?
N2 C10 N1 116.65(15) . . ?
O2 C11 N2 117.81(16) . . ?
O2 C11 C3 124.77(15) . . ?
N2 C11 C3 117.42(14) . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 H13 120.0 . . ?
C14 C13 C5 120.05(15) . . ?
C14 C13 H13 120.0 . . ?
O5 C14 C8 115.08(15) . . ?
O5 C14 C13 123.84(15) . . ?
C13 C14 C8 121.08(15) . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 C8 C14 O5 -0.45(19) . . . . ?
O1 C8 C14 C13 179.64(13) . . . . ?
O4 C2 C3 C4 1.0(2) . . . . ?
O4 C2 C3 C11 179.51(15) . . . . ?
N1 C2 C3 C4 -178.42(12) . . . . ?
N1 C2 C3 C11 0.1(2) . . . . ?
C1 N1 C2 O4 -2.7(2) . . . . ?
C1 N1 C2 C3 176.72(13) . . . . ?
C1 N1 C10 O3 1.3(2) . . . . ?
C1 N1 C10 N2 -178.35(13) . . . . ?
C2 N1 C10 O3 -179.08(15) . . . . ?
C2 N1 C10 N2 1.3(2) . . . . ?
C2 C3 C4 C5 -177.90(16) . . . . ?
C2 C3 C11 O2 -175.33(14) . . . . ?
C2 C3 C11 N2 4.1(2) . . . . ?
C3 C4 C5 C6 -178.03(16) . . . . ?
C3 C4 C5 C13 2.7(3) . . . . ?
C4 C3 C11 O2 2.9(2) . . . . ?
C4 C3 C11 N2 -177.63(13) . . . . ?
C4 C5 C6 C7 -179.66(13) . . . . ?
C4 C5 C13 C14 179.30(13) . . . . ?
C5 C6 C7 C8 0.4(2) . . . . ?
C5 C13 C14 O5 -179.75(13) . . . . ?
C5 C13 C14 C8 0.1(2) . . . . ?
C6 C5 C13 C14 0.1(2) . . . . ?
C6 C7 C8 O1 -179.89(14) . . . . ?
C6 C7 C8 C14 -0.2(2) . . . . ?
C7 C8 C14 O5 179.83(13) . . . . ?
C7 C8 C14 C13 -0.1(2) . . . . ?
C9 O1 C8 C7 8.8(2) . . . . ?
C9 O1 C8 C14 -170.87(14) . . . . ?
C10 N1 C2 O4 177.62(15) . . . . ?
C10 N1 C2 C3 -2.9(2) . . . . ?
C10 N2 C11 O2 173.28(14) . . . . ?
C10 N2 C11 C3 -6.2(2) . . . . ?
C11 N2 C10 O3 -176.03(14) . . . . ?
C11 N2 C10 N1 3.6(2) . . . . ?
C11 C3 C4 C5 3.8(3) . . . . ?
C12 N2 C10 O3 -1.5(2) . . . . ?
C12 N2 C10 N1 178.17(13) . . . . ?
C12 N2 C11 O2 -1.2(2) . . . . ?
C12 N2 C11 C3 179.30(13) . . . . ?
C13 C5 C6 C7 -0.3(2) . . . . ?
C15 O5 C14 C8 165.09(14) . . . . ?
C15 O5 C14 C13 -15.0(2) . . . . ?

_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_bb247
_database_code_depnum_ccdc_archive 'CCDC 2332071'
loop_
_audit_author_name
_audit_author_address
'Biswajit Bhattacharya'
;BAM Federal Institute for Materials Research and Testing
Germany
;
_audit_update_record             
;
2024-02-09 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_audit_creation_date             2023-02-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H16 N2 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_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                   7.0505(6)
_cell_length_b                   8.0193(7)
_cell_length_c                   13.9507(12)
_cell_angle_alpha                81.526(3)
_cell_angle_beta                 88.415(3)
_cell_angle_gamma                70.313(3)
_cell_volume                     734.36(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    400
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      26.75
_cell_measurement_theta_min      3.07
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27445
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.752
_diffrn_reflns_theta_min         3.069
_diffrn_ambient_temperature      300.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2617
_reflns_number_total             3033
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3033
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0664
_refine_ls_restrained_S_all      1.098
_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)+(0.1332P)²+0.1542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2091
_refine_ls_wR_factor_ref         0.2172
_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:
 C7(H7), C12(H12), C11(H11), C8(H8), C14(H14), C9(H9), C15(H15)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), 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
O3 O 0.6155(3) 0.62614(17) 0.31286(11) 0.0701(5) Uani 1 1 d . . . . .
O1 O 0.8237(3) -0.00190(18) 0.40159(11) 0.0696(5) Uani 1 1 d . . . . .
N2 N 0.7459(2) 0.12823(18) 0.24660(11) 0.0468(4) Uani 1 1 d . . . . .
O4 O 0.7515(3) 0.9765(2) 0.83888(11) 0.0706(5) Uani 1 1 d . . . . .
O2 O 0.6815(3) 0.2571(2) 0.09003(11) 0.0744(5) Uani 1 1 d . . . . .
N1 N 0.6468(2) 0.44086(19) 0.20238(11) 0.0514(4) Uani 1 1 d . . . . .
C4 C 0.6620(3) 0.4723(2) 0.29694(13) 0.0476(4) Uani 1 1 d . . . . .
C7 C 0.7767(3) 0.3227(2) 0.46332(13) 0.0482(4) Uani 1 1 d . . . . .
H7 H 0.8265 0.2127 0.5029 0.058 Uiso 1 1 calc R U . . .
C3 C 0.7340(2) 0.3147(2) 0.37055(12) 0.0426(4) Uani 1 1 d . . . . .
C2 C 0.7714(3) 0.1353(2) 0.34369(13) 0.0465(4) Uani 1 1 d . . . . .
C13 C 0.7688(3) 0.8427(3) 0.78552(14) 0.0518(5) Uani 1 1 d . . . . .
C1 C 0.6914(3) 0.2738(2) 0.17470(13) 0.0495(4) Uani 1 1 d . . . . .
C12 C 0.7252(3) 0.8962(3) 0.68668(14) 0.0560(5) Uani 1 1 d . . . . .
H12 H 0.6867 1.0170 0.6612 0.067 Uiso 1 1 calc R U . . .
C11 C 0.7386(3) 0.7718(3) 0.62651(14) 0.0540(5) Uani 1 1 d . . . . .
H11 H 0.7104 0.8091 0.5605 0.065 Uiso 1 1 calc R U . . .
C10 C 0.7943(3) 0.5895(3) 0.66343(13) 0.0514(5) Uani 1 1 d . . . . .
C8 C 0.7567(3) 0.4748(3) 0.50954(14) 0.0530(5) Uani 1 1 d . . . . .
H8 H 0.7107 0.5894 0.4745 0.064 Uiso 1 1 calc R U . . .
C14 C 0.8270(3) 0.6637(3) 0.82315(14) 0.0593(5) Uani 1 1 d . . . . .
H14 H 0.8577 0.6265 0.8889 0.071 Uiso 1 1 calc R U . . .
C9 C 0.8051(3) 0.4509(3) 0.60435(14) 0.0556(5) Uani 1 1 d . . . . .
H9 H 0.8504 0.3333 0.6356 0.067 Uiso 1 1 calc R U . . .
C5 C 0.7830(4) -0.0475(3) 0.21657(17) 0.0648(6) Uani 1 1 d . . . . .
H5A H 0.9167 -0.0898 0.1920 0.097 Uiso 1 1 calc R U . . .
H5B H 0.6868 -0.0373 0.1668 0.097 Uiso 1 1 calc R U . . .
H5C H 0.7699 -0.1305 0.2712 0.097 Uiso 1 1 calc R U . . .
C15 C 0.8393(3) 0.5395(3) 0.76163(15) 0.0607(5) Uani 1 1 d . . . . .
H15 H 0.8791 0.4188 0.7872 0.073 Uiso 1 1 calc R U . . .
C6 C 0.5826(5) 0.5951(3) 0.12580(17) 0.0841(8) Uani 1 1 d . . . . .
H6A H 0.5137 0.7011 0.1539 0.126 Uiso 1 1 calc R U . . .
H6B H 0.4935 0.5766 0.0809 0.126 Uiso 1 1 calc R U . . .
H6C H 0.6985 0.6088 0.0924 0.126 Uiso 1 1 calc R U . . .
C16 C 0.7785(4) 0.9297(4) 0.94105(18) 0.0797(7) Uani 1 1 d . . . . .
H16A H 0.9144 0.8520 0.9563 0.120 Uiso 1 1 calc R U . . .
H16B H 0.6867 0.8694 0.9657 0.120 Uiso 1 1 calc R U . . .
H16C H 0.7528 1.0362 0.9702 0.120 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
O3 C4 1.218(2) . ?
O1 C2 1.216(2) . ?
N2 C2 1.383(2) . ?
N2 C1 1.375(2) . ?
N2 C5 1.466(2) . ?
O4 C13 1.364(2) . ?
O4 C16 1.420(3) . ?
O2 C1 1.215(2) . ?
N1 C4 1.393(2) . ?
N1 C1 1.380(2) . ?
N1 C6 1.461(2) . ?
C4 C3 1.457(2) . ?
C7 H7 0.9300 . ?
C7 C3 1.352(2) . ?
C7 C8 1.426(2) . ?
C3 C2 1.476(2) . ?
C13 C12 1.393(3) . ?
C13 C14 1.378(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.374(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.400(3) . ?
C10 C9 1.459(3) . ?
C10 C15 1.384(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.345(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.387(3) . ?
C9 H9 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C15 H15 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 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
C2 N2 C5 118.17(15) . . ?
C1 N2 C2 125.09(14) . . ?
C1 N2 C5 116.73(15) . . ?
C13 O4 C16 117.77(17) . . ?
C4 N1 C6 118.10(16) . . ?
C1 N1 C4 124.90(15) . . ?
C1 N1 C6 116.98(16) . . ?
O3 C4 N1 119.02(17) . . ?
O3 C4 C3 124.59(17) . . ?
N1 C4 C3 116.39(15) . . ?
C3 C7 H7 115.2 . . ?
C3 C7 C8 129.62(17) . . ?
C8 C7 H7 115.2 . . ?
C4 C3 C2 119.63(15) . . ?
C7 C3 C4 123.21(15) . . ?
C7 C3 C2 117.11(16) . . ?
O1 C2 N2 120.10(16) . . ?
O1 C2 C3 123.56(17) . . ?
N2 C2 C3 116.34(15) . . ?
O4 C13 C12 115.90(18) . . ?
O4 C13 C14 124.32(18) . . ?
C14 C13 C12 119.78(17) . . ?
N2 C1 N1 117.40(15) . . ?
O2 C1 N2 121.66(17) . . ?
O2 C1 N1 120.94(18) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 C13 120.47(19) . . ?
C11 C12 H12 119.8 . . ?
C12 C11 H11 119.6 . . ?
C12 C11 C10 120.72(18) . . ?
C10 C11 H11 119.6 . . ?
C11 C10 C9 123.63(18) . . ?
C15 C10 C11 117.69(17) . . ?
C15 C10 C9 118.68(18) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.39(18) . . ?
C9 C8 H8 120.3 . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.14(18) . . ?
C15 C14 H14 120.4 . . ?
C10 C9 H9 116.5 . . ?
C8 C9 C10 127.05(19) . . ?
C8 C9 H9 116.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C10 C15 C14 122.18(19) . . ?
C10 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
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 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O3 C4 C3 C7 -7.1(3) . . . . ?
O3 C4 C3 C2 175.47(17) . . . . ?
O4 C13 C12 C11 179.84(16) . . . . ?
O4 C13 C14 C15 180.00(18) . . . . ?
N1 C4 C3 C7 172.86(16) . . . . ?
N1 C4 C3 C2 -4.6(2) . . . . ?
C4 N1 C1 N2 3.2(3) . . . . ?
C4 N1 C1 O2 -177.24(18) . . . . ?
C4 C3 C2 O1 -176.91(17) . . . . ?
C4 C3 C2 N2 3.8(2) . . . . ?
C7 C3 C2 O1 5.5(3) . . . . ?
C7 C3 C2 N2 -173.86(14) . . . . ?
C7 C8 C9 C10 -179.94(17) . . . . ?
C3 C7 C8 C9 178.63(18) . . . . ?
C2 N2 C1 O2 176.24(18) . . . . ?
C2 N2 C1 N1 -4.2(3) . . . . ?
C13 C12 C11 C10 0.7(3) . . . . ?
C13 C14 C15 C10 -0.2(3) . . . . ?
C1 N2 C2 O1 -178.60(17) . . . . ?
C1 N2 C2 C3 0.7(3) . . . . ?
C1 N1 C4 O3 -178.94(18) . . . . ?
C1 N1 C4 C3 1.1(3) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C12 C11 C10 C9 177.92(17) . . . . ?
C12 C11 C10 C15 -1.4(3) . . . . ?
C11 C10 C9 C8 -3.2(3) . . . . ?
C11 C10 C15 C14 1.2(3) . . . . ?
C8 C7 C3 C4 2.4(3) . . . . ?
C8 C7 C3 C2 179.89(17) . . . . ?
C14 C13 C12 C11 0.4(3) . . . . ?
C9 C10 C15 C14 -178.16(18) . . . . ?
C5 N2 C2 O1 0.2(3) . . . . ?
C5 N2 C2 C3 179.51(16) . . . . ?
C5 N2 C1 O2 -2.5(3) . . . . ?
C5 N2 C1 N1 177.04(16) . . . . ?
C15 C10 C9 C8 176.18(19) . . . . ?
C6 N1 C4 O3 2.3(3) . . . . ?
C6 N1 C4 C3 -177.66(19) . . . . ?
C6 N1 C1 N2 -178.02(19) . . . . ?
C6 N1 C1 O2 1.6(3) . . . . ?
C16 O4 C13 C12 174.99(19) . . . . ?
C16 O4 C13 C14 -5.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
