# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_hsp-ahp-i-272-s
_database_code_depnum_ccdc_archive 'CCDC 1905862'
loop_
_audit_author_name
_audit_author_address
'Ashiq Hussain padder'
;Pondicherry  university
India
;
_audit_update_record             
;
2019-03-26 deposited with the CCDC.	2020-03-17 downloaded from the CCDC.
;
_audit_creation_date             2019-03-27
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H15 N O3'
_chemical_formula_sum            'C14 H15 N O3'
_chemical_formula_weight         245.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H15 O3 N'
_chemical_oxdiff_usercomment     ' COLOURLESS PLATE, 295K, 0.42 0.40 0.05'
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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y, -z'
3 'x+1/2, y+1/2, z+1/2'
4 '-x+1, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, -y, z'
7 '-x+1/2, -y+1/2, -z+1/2'
8 'x, -y+1/2, z+1/2'

_cell_length_a                   25.920(3)
_cell_length_b                   5.4308(6)
_cell_length_c                   18.988(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.173(13)
_cell_angle_gamma                90.00
_cell_volume                     2602.5(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1406
_cell_measurement_temperature    295
_cell_measurement_theta_max      29.1191
_cell_measurement_theta_min      3.8301
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6451
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.18
_diffrn_reflns_theta_min         3.84
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -37.00   48.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00   25.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -61.00   56.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   19.0000  -30.0000 117

#__ type_ start__ end____ width___ exp.time_
  4 omega  -54.00  -20.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0585  -21.0000   10.0000 34
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0006552000
_diffrn_orient_matrix_UB_12      -0.0079075000
_diffrn_orient_matrix_UB_13      -0.0370103000
_diffrn_orient_matrix_UB_21      -0.0264265000
_diffrn_orient_matrix_UB_22      -0.0450249000
_diffrn_orient_matrix_UB_23      -0.0081901000
_diffrn_orient_matrix_UB_31      -0.0096816000
_diffrn_orient_matrix_UB_32      0.1224220000
_diffrn_orient_matrix_UB_33      -0.0053443000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1786
_reflns_number_total             3012
_reflns_odcompleteness_completeness 98.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3012
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0615
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0819P)²+0.9382P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1904
_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 > 2sigma(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. 
;
_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
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.20264(6) 0.8586(3) 0.19855(8) 0.0661(5) Uani 1 d . . .
N2 N 0.22654(6) 1.1426(3) 0.32632(9) 0.0559(5) Uani 1 d . . .
H2 H 0.2404 1.0183 0.3095 0.067 Uiso 1 calc . . R
C3 C 0.18053(8) 1.2529(4) 0.29034(11) 0.0514(5) Uani 1 d . . .
C4 C 0.16254(8) 0.9822(4) 0.18413(11) 0.0563(5) Uani 1 d . . .
C5 C 0.16975(8) 1.4728(4) 0.33401(11) 0.0538(5) Uani 1 d . . .
H5 H 0.1767 1.6220 0.3087 0.065 Uiso 1 calc . . R
O6 O 0.12374(6) 0.9435(4) 0.12573(9) 0.0824(6) Uani 1 d . . .
C7 C 0.15011(8) 1.1833(4) 0.22657(11) 0.0579(6) Uani 1 d . . .
H7 H 0.1190 1.2707 0.2087 0.070 Uiso 1 calc . . R
C9 C 0.11349(8) 1.4865(4) 0.34291(11) 0.0536(5) Uani 1 d . . .
C10 C 0.21287(9) 1.4528(5) 0.40412(12) 0.0636(6) Uani 1 d . . .
H10A H 0.2324 1.6061 0.4140 0.076 Uiso 1 calc . . R
H10B H 0.1973 1.4151 0.4447 0.076 Uiso 1 calc . . R
C11 C 0.24852(9) 1.2497(5) 0.39201(12) 0.0621(6) Uani 1 d . . .
C12 C 0.00988(10) 1.5117(5) 0.35978(15) 0.0800(8) Uani 1 d . . .
H12 H -0.0245 1.5217 0.3666 0.096 Uiso 1 calc . . R
C13 C 0.07994(10) 1.6708(4) 0.31172(14) 0.0729(7) Uani 1 d . . .
H13 H 0.0921 1.7905 0.2844 0.088 Uiso 1 calc . . R
C14 C 0.09363(10) 1.3121(5) 0.38139(17) 0.0863(9) Uani 1 d . . .
H14 H 0.1152 1.1824 0.4023 0.104 Uiso 1 calc . . R
C15 C 0.02814(10) 1.6823(5) 0.32012(16) 0.0842(8) Uani 1 d . . .
H15 H 0.0060 1.8086 0.2982 0.101 Uiso 1 calc . . R
C16 C 0.04239(11) 1.3250(6) 0.38971(19) 0.0967(10) Uani 1 d . . .
H16 H 0.0298 1.2041 0.4162 0.116 Uiso 1 calc . . R
C17 C 0.13196(11) 0.7535(7) 0.07599(18) 0.1057(11) Uani 1 d . . .
H17A H 0.1480 0.8251 0.0393 0.127 Uiso 1 calc . . R
H17B H 0.1561 0.6303 0.1020 0.127 Uiso 1 calc . . R
C1 C 0.08445(15) 0.6425(9) 0.0431(3) 0.164(2) Uani 1 d . . .
H1A H 0.0910 0.5136 0.0116 0.247 Uiso 1 calc . . GR
H1B H 0.0612 0.7628 0.0154 0.247 Uiso 1 calc . . GR
H1C H 0.0682 0.5742 0.0794 0.247 Uiso 1 calc . . GR
O2 O 0.28927(7) 1.1841(4) 0.43162(9) 0.0917(7) Uani 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
O1 C4 1.215(2) . ?
N2 H2 0.8600 . ?
N2 C3 1.370(3) . ?
N2 C11 1.376(3) . ?
C3 C5 1.516(3) . ?
C3 C7 1.340(3) . ?
C4 O6 1.333(2) . ?
C4 C7 1.437(3) . ?
C5 H5 0.9800 . ?
C5 C9 1.508(3) . ?
C5 C10 1.535(3) . ?
O6 C17 1.447(3) . ?
C7 H7 0.9300 . ?
C9 C13 1.369(3) . ?
C9 C14 1.367(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.490(3) . ?
C11 O2 1.202(3) . ?
C12 H12 0.9300 . ?
C12 C15 1.346(4) . ?
C12 C16 1.358(4) . ?
C13 H13 0.9300 . ?
C13 C15 1.389(4) . ?
C14 H14 0.9300 . ?
C14 C16 1.375(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C1 1.386(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N2 H2 123.2 . . ?
C3 N2 C11 113.64(19) . . ?
C11 N2 H2 123.2 . . ?
N2 C3 C5 108.65(17) . . ?
C7 C3 N2 126.4(2) . . ?
C7 C3 C5 124.9(2) . . ?
O1 C4 O6 123.0(2) . . ?
O1 C4 C7 125.7(2) . . ?
O6 C4 C7 111.30(19) . . ?
C3 C5 H5 107.8 . . ?
C3 C5 C10 103.31(17) . . ?
C9 C5 C3 113.82(17) . . ?
C9 C5 H5 107.8 . . ?
C9 C5 C10 115.98(17) . . ?
C10 C5 H5 107.8 . . ?
C4 O6 C17 117.4(2) . . ?
C3 C7 C4 124.1(2) . . ?
C3 C7 H7 118.0 . . ?
C4 C7 H7 118.0 . . ?
C13 C9 C5 121.53(19) . . ?
C14 C9 C5 121.2(2) . . ?
C14 C9 C13 117.3(2) . . ?
C5 C10 H10A 110.6 . . ?
C5 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
C11 C10 C5 105.85(18) . . ?
C11 C10 H10A 110.6 . . ?
C11 C10 H10B 110.6 . . ?
N2 C11 C10 108.01(19) . . ?
O2 C11 N2 124.4(2) . . ?
O2 C11 C10 127.6(2) . . ?
C15 C12 H12 120.5 . . ?
C15 C12 C16 119.0(2) . . ?
C16 C12 H12 120.5 . . ?
C9 C13 H13 119.4 . . ?
C9 C13 C15 121.2(2) . . ?
C15 C13 H13 119.4 . . ?
C9 C14 H14 119.4 . . ?
C9 C14 C16 121.2(2) . . ?
C16 C14 H14 119.4 . . ?
C12 C15 C13 120.4(2) . . ?
C12 C15 H15 119.8 . . ?
C13 C15 H15 119.8 . . ?
C12 C16 C14 120.9(3) . . ?
C12 C16 H16 119.5 . . ?
C14 C16 H16 119.5 . . ?
O6 C17 H17A 109.5 . . ?
O6 C17 H17B 109.5 . . ?
H17A C17 H17B 108.0 . . ?
C1 C17 O6 110.9(2) . . ?
C1 C17 H17A 109.5 . . ?
C1 C17 H17B 109.5 . . ?
C17 C1 H1A 109.5 . . ?
C17 C1 H1B 109.5 . . ?
C17 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C4 O6 C17 -3.5(4) . . . . ?
O1 C4 C7 C3 -3.6(4) . . . . ?
N2 C3 C5 C9 -133.00(18) . . . . ?
N2 C3 C5 C10 -6.4(2) . . . . ?
N2 C3 C7 C4 -2.2(3) . . . . ?
C3 N2 C11 C10 1.9(3) . . . . ?
C3 N2 C11 O2 -178.7(2) . . . . ?
C3 C5 C9 C13 -113.1(2) . . . . ?
C3 C5 C9 C14 65.6(3) . . . . ?
C3 C5 C10 C11 7.2(2) . . . . ?
C4 O6 C17 C1 148.1(4) . . . . ?
C5 C3 C7 C4 176.47(19) . . . . ?
C5 C9 C13 C15 180.0(2) . . . . ?
C5 C9 C14 C16 179.8(3) . . . . ?
C5 C10 C11 N2 -5.9(2) . . . . ?
C5 C10 C11 O2 174.8(3) . . . . ?
O6 C4 C7 C3 175.8(2) . . . . ?
C7 C3 C5 C9 48.1(3) . . . . ?
C7 C3 C5 C10 174.7(2) . . . . ?
C7 C4 O6 C17 177.1(2) . . . . ?
C9 C5 C10 C11 132.5(2) . . . . ?
C9 C13 C15 C12 0.4(4) . . . . ?
C9 C14 C16 C12 0.1(5) . . . . ?
C10 C5 C9 C13 127.2(2) . . . . ?
C10 C5 C9 C14 -54.1(3) . . . . ?
C11 N2 C3 C5 3.0(2) . . . . ?
C11 N2 C3 C7 -178.1(2) . . . . ?
C13 C9 C14 C16 -1.4(4) . . . . ?
C14 C9 C13 C15 1.2(4) . . . . ?
C15 C12 C16 C14 1.6(5) . . . . ?
C16 C12 C15 C13 -1.8(5) . . . . ?

_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_HSP-AHP-II-85-AS
_database_code_depnum_ccdc_archive 'CCDC 1912295'
loop_
_audit_author_name
_audit_author_address
'sharada d'
;PONDICHERRY UNIVERSITY
India
;
_audit_update_record             
;
2019-04-25 deposited with the CCDC.	2020-03-17 downloaded from the CCDC.
;
_audit_creation_date             2019-04-25
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_chemical_formula_moiety         'C15 H15 N O4'
_chemical_formula_sum            'C15 H15 N O4'
_chemical_formula_weight         273.29
_chemical_oxdiff_formula         'C12 H20 N1 O2'
_chemical_oxdiff_usercomment     'YELLOW COLOUR BLOCK, 298K, 0.86 0.44 0.24'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   16.6907(12)
_cell_length_b                   4.2138(3)
_cell_length_c                   19.6741(12)
_cell_angle_alpha                90
_cell_angle_beta                 103.083(7)
_cell_angle_gamma                90
_cell_volume                     1347.79(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2238
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.2773
_cell_measurement_theta_min      3.5756
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.3467
_exptl_crystal_description       block
_exptl_crystal_F_000             576.3374
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.24
_diffrn_reflns_av_R_equivalents  0.0123
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5482
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         29.34
_diffrn_reflns_theta_min         3.64
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9974
_diffrn_measured_fraction_theta_max 0.8155
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -11.00   21.00   1.0000   28.0800
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
  2 omega    1.00   88.00   1.0000   28.0800
omega____ theta____ kappa____ phi______ frames
    -       19.8397   37.0000 -150.0000 87

#__ type_ start__ end____ width___ exp.time_
  3 omega   -5.00   92.00   1.0000   28.0800
omega____ theta____ kappa____ phi______ frames
    -       19.8397   37.0000  120.0000 97
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0296594000
_diffrn_orient_matrix_UB_12      -0.0012378000
_diffrn_orient_matrix_UB_13      -0.0321325000
_diffrn_orient_matrix_UB_21      0.0320120000
_diffrn_orient_matrix_UB_22      -0.0063792000
_diffrn_orient_matrix_UB_23      -0.0182922000
_diffrn_orient_matrix_UB_31      -0.0009832000
_diffrn_orient_matrix_UB_32      -0.1682706000
_diffrn_orient_matrix_UB_33      0.0009128000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -22
_reflns_limit_k_max              5
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              -14
_reflns_number_gt                2553
_reflns_number_total             3011
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.2338
_refine_diff_density_min         -0.2078
_refine_diff_density_rms         0.0436
_refine_ls_d_res_high            0.7252
_refine_ls_d_res_low             5.6043
_refine_ls_goodness_of_fit_ref   1.0538
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3011
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.0538
_refine_ls_shift/su_max          0.0011
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+0.2617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1054
_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
2.a Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C5(H5), C11(H11), C12(H12), N2(H2), C1(H1)
2.c Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C15(H15a,H15b,H15c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
O2 O 0.79791(5) 0.8039(2) 0.22044(4) 0.0429(2) Uani 1.000000 .
O3 O 0.88973(5) 0.5477(2) 0.17236(4) 0.0405(2) Uani 1.000000 .
N2 N 0.67348(6) 1.1410(3) 0.12496(5) 0.0364(2) Uani 1.000000 .
C10 C 0.78423(7) 1.1149(3) -0.05731(6) 0.0359(3) Uani 1.000000 .
H10 H 0.81748(7) 1.2223(3) -0.02010(6) 0.0431(3) Uiso 1.000000 R
C13 C 0.76429(8) 0.8808(3) -0.17121(6) 0.0433(3) Uani 1.000000 .
H13 H 0.78434(8) 0.8303(3) -0.21028(6) 0.0519(4) Uiso 1.000000 R
O4 O 0.88880(6) 1.1364(3) -0.12594(6) 0.0573(3) Uani 1.000000 .
O1 O 0.55108(6) 1.4176(3) 0.11237(5) 0.0562(3) Uani 1.000000 .
C3 C 0.71862(7) 1.0126(3) 0.08105(6) 0.0314(3) Uani 1.000000 .
C6 C 0.82332(7) 0.7314(3) 0.16962(6) 0.0324(3) Uani 1.000000 .
C9 C 0.70495(7) 1.0196(3) -0.05371(6) 0.0334(3) Uani 1.000000 .
C4 C 0.67401(7) 1.0973(3) 0.00899(6) 0.0336(3) Uani 1.000000 .
C14 C 0.81298(8) 1.0485(3) -0.11664(6) 0.0383(3) Uani 1.000000 .
C5 C 0.78640(7) 0.8305(3) 0.09810(6) 0.0345(3) Uani 1.000000 .
H5 H 0.81106(7) 0.7642(3) 0.06262(6) 0.0414(3) Uiso 1.000000 R
C11 C 0.65538(8) 0.8599(3) -0.10945(6) 0.0409(3) Uani 1.000000 .
H11 H 0.60212(8) 0.8011(3) -0.10786(6) 0.0491(4) Uiso 1.000000 R
C0aa C 0.60279(7) 1.2851(3) 0.08747(6) 0.0396(3) Uani 1.000000 .
C7 C 0.93085(8) 0.4340(3) 0.24163(6) 0.0399(3) Uani 1.000000 .
H7a H 0.94500(8) 0.6112(3) 0.27357(6) 0.0479(4) Uiso 1.000000 R
H7b H 0.89493(8) 0.2920(3) 0.25972(6) 0.0479(4) Uiso 1.000000 R
C8 C 1.00690(8) 0.2627(4) 0.23440(8) 0.0533(4) Uani 1.000000 .
H8a H 0.99231(10) 0.0931(17) 0.2014(4) 0.0800(6) Uiso 1.000000 GR
H8b H 1.0430(3) 0.4078(7) 0.2184(6) 0.0800(6) Uiso 1.000000 GR
H8c H 1.0343(4) 0.177(2) 0.27885(15) 0.0800(6) Uiso 1.000000 GR
C1 C 0.60482(7) 1.2474(3) 0.01312(6) 0.0407(3) Uani 1.000000 .
C12 C 0.68625(9) 0.7890(4) -0.16761(7) 0.0462(3) Uani 1.000000 .
H12 H 0.65372(9) 0.6779(4) -0.20461(7) 0.0555(4) Uiso 1.000000 R
C15 C 0.94071(9) 1.3159(4) -0.07301(9) 0.0585(4) Uani 1.000000 .
H15a H 0.9917(3) 1.358(2) -0.0861(3) 0.0878(6) Uiso 1.000000 GR
H15b H 0.9143(3) 1.5130(13) -0.0669(4) 0.0878(6) Uiso 1.000000 GR
H15c H 0.9513(6) 1.1987(13) -0.03007(18) 0.0878(6) Uiso 1.000000 GR
H2 H 0.68746(6) 1.1325(3) 0.16976(5) 0.0437(3) Uiso 1.000000 R
H1 H 0.56445(7) 1.3170(3) -0.02462(6) 0.0488(4) Uiso 1.000000 R


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
O2 C6 1.2103(14) . ?
O3 C6 1.3429(14) . ?
O3 C7 1.4612(14) . ?
N2 C3 1.3789(14) . ?
N2 C0aa 1.3823(16) . ?
C10 C9 1.3999(16) . ?
C10 C14 1.3873(16) . ?
C13 C14 1.3846(18) . ?
C13 C12 1.3759(19) . ?
O4 C14 1.3700(15) . ?
O4 C15 1.4137(19) . ?
O1 C0aa 1.2198(15) . ?
C3 C4 1.4879(15) . ?
C3 C5 1.3449(16) . ?
C6 C5 1.4634(16) . ?
C9 C4 1.4780(15) . ?
C9 C11 1.3890(17) . ?
C4 C1 1.3351(17) . ?
C11 C12 1.3897(18) . ?
C0aa C1 1.4793(17) . ?
C7 C8 1.4946(18) . ?

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
C7 O3 C6 115.83(9) . . ?
C0aa N2 C3 111.07(9) . . ?
C14 C10 C9 119.71(11) . . ?
C12 C13 C14 120.00(11) . . ?
C15 O4 C14 118.49(11) . . ?
C4 C3 N2 106.03(10) . . ?
C5 C3 N2 128.00(10) . . ?
C5 C3 C4 125.86(10) . . ?
O3 C6 O2 123.56(10) . . ?
C5 C6 O2 124.90(11) . . ?
C5 C6 O3 111.54(9) . . ?
C4 C9 C10 119.44(10) . . ?
C11 C9 C10 120.01(11) . . ?
C11 C9 C4 120.53(11) . . ?
C9 C4 C3 123.23(10) . . ?
C1 C4 C3 108.00(10) . . ?
C1 C4 C9 128.77(11) . . ?
C13 C14 C10 120.08(11) . . ?
O4 C14 C10 124.31(12) . . ?
O4 C14 C13 115.61(11) . . ?
C6 C5 C3 123.36(10) . . ?
C12 C11 C9 119.25(12) . . ?
O1 C0aa N2 125.65(11) . . ?
C1 C0aa N2 105.82(10) . . ?
C1 C0aa O1 128.53(12) . . ?
C8 C7 O3 107.42(10) . . ?
C0aa C1 C4 108.95(10) . . ?
C11 C12 C13 120.91(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
