# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_38
_database_code_depnum_ccdc_archive 'CCDC 2070969'
loop_
_audit_author_name
_audit_author_address
'Srinu Tothadi'
;CSIR National Chemical Laboratory Pune
India
;
_audit_update_record             
;
2021-03-17 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;
_audit_creation_date             2021-02-08
_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         'C18 H14 N2 O2'
_chemical_formula_sum            'C18 H14 N2 O2'
_chemical_formula_weight         290.31
_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                   7.2558(7)
_cell_length_b                   9.8044(10)
_cell_length_c                   10.5031(10)
_cell_angle_alpha                99.055(4)
_cell_angle_beta                 105.174(4)
_cell_angle_gamma                103.419(4)
_cell_volume                     682.24(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.67
_cell_measurement_theta_min      2.20
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_correction_T_min  0.6098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1347 before and 0.0804 after correction. The Ratio of minimum to maximum transmission is 0.8163. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13705
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.496
_diffrn_reflns_theta_min         2.196
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_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                2473
_reflns_number_total             2806
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2806
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.105
_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)+(0.0656P)²+0.3229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1310
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C18(H18)
;
_atom_sites_solution_hydrogens   mixed
_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 0.61770(16) 0.72816(12) 0.43736(11) 0.0180(3) Uani 1 1 d . . . . .
O2 O 0.25385(16) 1.02817(11) 0.35165(11) 0.0176(3) Uani 1 1 d . . . . .
N1 N 0.31154(19) 0.59129(13) 0.13045(13) 0.0154(3) Uani 1 1 d . . . . .
N2 N 0.3849(2) 0.83748(13) 0.31900(13) 0.0154(3) Uani 1 1 d . . . . .
C1 C 0.1582(2) 0.26336(18) -0.14647(16) 0.0210(4) Uani 1 1 d . . . . .
H1A H 0.1252 0.2300 -0.2418 0.025 Uiso 1 1 calc R . . . .
C2 C 0.2112(2) 0.40988(17) -0.09105(16) 0.0199(3) Uani 1 1 d . . . . .
H2 H 0.2176 0.4777 -0.1463 0.024 Uiso 1 1 calc R . . . .
C3 C 0.2549(2) 0.45431(16) 0.04936(15) 0.0157(3) Uani 1 1 d . . . . .
C4 C 0.3355(2) 0.57914(16) 0.26317(15) 0.0148(3) Uani 1 1 d . . . . .
C5 C 0.4119(2) 0.71289(15) 0.37588(15) 0.0149(3) Uani 1 1 d . . . . .
C6 C 0.2990(2) 0.72036(16) 0.47870(15) 0.0151(3) Uani 1 1 d . . . . .
C7 C 0.2593(2) 0.62759(17) 0.56164(15) 0.0181(3) Uani 1 1 d . . . . .
H7 H 0.2999 0.5420 0.5576 0.022 Uiso 1 1 calc R . . . .
C8 C 0.1574(3) 0.66511(17) 0.65116(16) 0.0212(4) Uani 1 1 d . . . . .
H8 H 0.1249 0.6022 0.7072 0.025 Uiso 1 1 calc R . . . .
C9 C 0.1019(2) 0.79222(18) 0.66062(16) 0.0199(3) Uani 1 1 d . . . . .
H9 H 0.0352 0.8157 0.7240 0.024 Uiso 1 1 calc R . . . .
C10 C 0.1521(2) 0.16284(17) -0.06484(17) 0.0206(4) Uani 1 1 d . . . . .
H10 H 0.1155 0.0629 -0.1060 0.025 Uiso 1 1 calc R . . . .
C11 C 0.1985(2) 0.20681(17) 0.07472(16) 0.0186(3) Uani 1 1 d . . . . .
H11 H 0.1966 0.1383 0.1294 0.022 Uiso 1 1 calc R . . . .
C12 C 0.2486(2) 0.35508(16) 0.13367(15) 0.0157(3) Uani 1 1 d . . . . .
C13 C 0.3001(2) 0.43783(16) 0.26932(15) 0.0162(3) Uani 1 1 d . . . . .
H13 H 0.3082 0.4014 0.3486 0.019 Uiso 1 1 calc R . . . .
C14 C 0.3168(2) 0.72316(16) 0.08141(15) 0.0169(3) Uani 1 1 d . . . . .
H14A H 0.1793 0.7292 0.0449 0.020 Uiso 1 1 calc R . . . .
H14B H 0.3778 0.7215 0.0074 0.020 Uiso 1 1 calc R . . . .
C15 C 0.4380(2) 0.85448(16) 0.19746(15) 0.0169(3) Uani 1 1 d . . . . .
H15A H 0.5821 0.8650 0.2149 0.020 Uiso 1 1 calc R . . . .
H15B H 0.4112 0.9427 0.1720 0.020 Uiso 1 1 calc R . . . .
C16 C 0.2905(2) 0.91816(15) 0.38063(14) 0.0143(3) Uani 1 1 d . . . . .
C17 C 0.2399(2) 0.84555(16) 0.48618(15) 0.0150(3) Uani 1 1 d . . . . .
C18 C 0.1435(2) 0.88500(16) 0.57793(15) 0.0172(3) Uani 1 1 d . . . . .
H18 H 0.1073 0.9723 0.5840 0.021 Uiso 1 1 calc R . . . .
H1 H 0.666(4) 0.807(3) 0.509(3) 0.047(7) Uiso 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
O1 C5 1.4246(18) . ?
O1 H1 0.91(3) . ?
O2 C16 1.2332(18) . ?
N1 C3 1.3779(19) . ?
N1 C4 1.3866(19) . ?
N1 C14 1.4613(18) . ?
N2 C5 1.4720(18) . ?
N2 C15 1.4494(18) . ?
N2 C16 1.355(2) . ?
C1 H1A 0.9500 . ?
C1 C2 1.383(2) . ?
C1 C10 1.405(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.398(2) . ?
C3 C12 1.416(2) . ?
C4 C5 1.503(2) . ?
C4 C13 1.364(2) . ?
C5 C6 1.520(2) . ?
C6 C7 1.389(2) . ?
C6 C17 1.389(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.396(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.393(2) . ?
C9 H9 0.9500 . ?
C9 C18 1.390(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.408(2) . ?
C12 C13 1.430(2) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.528(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.487(2) . ?
C17 C18 1.389(2) . ?
C18 H18 0.9500 . ?

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
C5 O1 H1 107.6(16) . . ?
C3 N1 C4 107.94(12) . . ?
C3 N1 C14 125.20(12) . . ?
C4 N1 C14 126.33(12) . . ?
C15 N2 C5 119.32(12) . . ?
C16 N2 C5 114.28(12) . . ?
C16 N2 C15 126.01(12) . . ?
C2 C1 H1A 119.3 . . ?
C2 C1 C10 121.45(15) . . ?
C10 C1 H1A 119.3 . . ?
C1 C2 H2 121.3 . . ?
C1 C2 C3 117.46(14) . . ?
C3 C2 H2 121.3 . . ?
N1 C3 C2 129.75(14) . . ?
N1 C3 C12 108.09(13) . . ?
C2 C3 C12 122.15(14) . . ?
N1 C4 C5 119.65(13) . . ?
C13 C4 N1 110.27(13) . . ?
C13 C4 C5 129.76(14) . . ?
O1 C5 N2 111.12(12) . . ?
O1 C5 C4 106.20(12) . . ?
O1 C5 C6 112.50(12) . . ?
N2 C5 C4 109.31(12) . . ?
N2 C5 C6 101.15(12) . . ?
C4 C5 C6 116.54(12) . . ?
C7 C6 C5 129.94(14) . . ?
C7 C6 C17 120.76(15) . . ?
C17 C6 C5 109.25(13) . . ?
C6 C7 H7 121.3 . . ?
C6 C7 C8 117.32(15) . . ?
C8 C7 H7 121.3 . . ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.85(15) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 H9 119.8 . . ?
C18 C9 C8 120.44(15) . . ?
C18 C9 H9 119.8 . . ?
C1 C10 H10 119.4 . . ?
C11 C10 C1 121.19(14) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.62(14) . . ?
C12 C11 H11 120.7 . . ?
C3 C12 C13 106.76(13) . . ?
C11 C12 C3 119.11(14) . . ?
C11 C12 C13 134.13(14) . . ?
C4 C13 C12 106.91(13) . . ?
C4 C13 H13 126.5 . . ?
C12 C13 H13 126.5 . . ?
N1 C14 H14A 109.7 . . ?
N1 C14 H14B 109.7 . . ?
N1 C14 C15 109.83(12) . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
N2 C15 C14 109.89(12) . . ?
N2 C15 H15A 109.7 . . ?
N2 C15 H15B 109.7 . . ?
C14 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
O2 C16 N2 125.78(14) . . ?
O2 C16 C17 128.20(14) . . ?
N2 C16 C17 106.01(12) . . ?
C6 C17 C16 108.89(13) . . ?
C18 C17 C6 121.93(14) . . ?
C18 C17 C16 129.14(14) . . ?
C9 C18 H18 121.2 . . ?
C17 C18 C9 117.66(14) . . ?
C17 C18 H18 121.2 . . ?

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 C5 C6 C7 -65.2(2) . . . . ?
O1 C5 C6 C17 112.19(14) . . . . ?
O2 C16 C17 C6 176.54(14) . . . . ?
O2 C16 C17 C18 -1.3(3) . . . . ?
N1 C3 C12 C11 -178.56(13) . . . . ?
N1 C3 C12 C13 1.11(17) . . . . ?
N1 C4 C5 O1 -100.83(15) . . . . ?
N1 C4 C5 N2 19.13(19) . . . . ?
N1 C4 C5 C6 132.97(14) . . . . ?
N1 C4 C13 C12 -0.71(18) . . . . ?
N1 C14 C15 N2 -43.76(17) . . . . ?
N2 C5 C6 C7 176.17(15) . . . . ?
N2 C5 C6 C17 -6.45(15) . . . . ?
N2 C16 C17 C6 -2.62(16) . . . . ?
N2 C16 C17 C18 179.59(15) . . . . ?
C1 C2 C3 N1 179.77(15) . . . . ?
C1 C2 C3 C12 0.8(2) . . . . ?
C1 C10 C11 C12 1.3(2) . . . . ?
C2 C1 C10 C11 0.2(3) . . . . ?
C2 C3 C12 C11 0.6(2) . . . . ?
C2 C3 C12 C13 -179.70(14) . . . . ?
C3 N1 C4 C5 175.53(13) . . . . ?
C3 N1 C4 C13 1.42(18) . . . . ?
C3 N1 C14 C15 -164.84(14) . . . . ?
C3 C12 C13 C4 -0.25(17) . . . . ?
C4 N1 C3 C2 179.35(16) . . . . ?
C4 N1 C3 C12 -1.54(17) . . . . ?
C4 N1 C14 C15 24.5(2) . . . . ?
C4 C5 C6 C7 57.8(2) . . . . ?
C4 C5 C6 C17 -124.82(14) . . . . ?
C5 N2 C15 C14 59.25(17) . . . . ?
C5 N2 C16 O2 179.00(13) . . . . ?
C5 N2 C16 C17 -1.82(16) . . . . ?
C5 C4 C13 C12 -174.05(15) . . . . ?
C5 C6 C7 C8 177.51(14) . . . . ?
C5 C6 C17 C16 5.82(16) . . . . ?
C5 C6 C17 C18 -176.19(13) . . . . ?
C6 C7 C8 C9 -1.8(2) . . . . ?
C6 C17 C18 C9 -1.9(2) . . . . ?
C7 C6 C17 C16 -176.52(13) . . . . ?
C7 C6 C17 C18 1.5(2) . . . . ?
C7 C8 C9 C18 1.4(2) . . . . ?
C8 C9 C18 C17 0.5(2) . . . . ?
C10 C1 C2 C3 -1.2(2) . . . . ?
C10 C11 C12 C3 -1.6(2) . . . . ?
C10 C11 C12 C13 178.81(16) . . . . ?
C11 C12 C13 C4 179.35(17) . . . . ?
C13 C4 C5 O1 72.0(2) . . . . ?
C13 C4 C5 N2 -168.06(15) . . . . ?
C13 C4 C5 C6 -54.2(2) . . . . ?
C14 N1 C3 C2 7.3(3) . . . . ?
C14 N1 C3 C12 -173.60(14) . . . . ?
C14 N1 C4 C5 -12.5(2) . . . . ?
C14 N1 C4 C13 173.36(14) . . . . ?
C15 N2 C5 O1 72.11(16) . . . . ?
C15 N2 C5 C4 -44.79(17) . . . . ?
C15 N2 C5 C6 -168.27(12) . . . . ?
C15 N2 C16 O2 -8.2(2) . . . . ?
C15 N2 C16 C17 170.95(13) . . . . ?
C16 N2 C5 O1 -114.60(14) . . . . ?
C16 N2 C5 C4 128.51(13) . . . . ?
C16 N2 C5 C6 5.03(16) . . . . ?
C16 N2 C15 C14 -113.19(16) . . . . ?
C16 C17 C18 C9 175.66(14) . . . . ?
C17 C6 C7 C8 0.4(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_9
_database_code_depnum_ccdc_archive 'CCDC 2070970'
loop_
_audit_author_name
_audit_author_address
'Srinu Tothadi'
;CSIR National Chemical Laboratory Pune
India
;
_audit_update_record             
;
2021-03-17 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;
_audit_creation_date             2021-01-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 N2 O2'
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   24.406(2)
_cell_length_b                   5.0265(4)
_cell_length_c                   9.4136(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1154.83(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      2.73
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6874
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1020 before and 0.0670 after correction.
The Ratio of minimum to maximum transmission is 0.9221.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            38269
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.359
_diffrn_reflns_theta_min         1.669
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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         0.878
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2525
_reflns_number_total             2610
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 
;
 Flack x determined using 1127 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2610
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.194
_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)+(0.0622P)²+0.2327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1060
_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 O(H) groups
2. Restrained distances
 N2-H2A
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C4(H4), C13(H13)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C3(H3A,H3B), C2(H2B,H2C)
3.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C7(H7), C10(H10)
3.d Idealised tetrahedral OH refined as rotating group with stretchable bonds:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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
O2 O 0.50369(7) 0.4607(4) 0.4737(2) 0.0174(4) Uani 1 1 d . . . . .
H2 H 0.5189(12) 0.578(7) 0.528(3) 0.026 Uiso 1 1 calc GR . . . .
O1 O 0.45068(7) 0.1760(4) 0.1504(2) 0.0210(4) Uani 1 1 d . . . . .
N2 N 0.42375(8) 0.6202(4) 0.7360(2) 0.0151(4) Uani 1 1 d D . . . .
N1 N 0.40351(8) 0.2297(4) 0.3582(2) 0.0140(4) Uani 1 1 d . . . . .
C5 C 0.37017(9) 0.4984(5) 0.5524(3) 0.0136(5) Uani 1 1 d . . . . .
C6 C 0.34060(10) 0.6868(5) 0.6361(3) 0.0137(5) Uani 1 1 d . . . . .
C4 C 0.35498(10) 0.3662(5) 0.4159(3) 0.0139(5) Uani 1 1 d . . . . .
H4 H 0.324849 0.234980 0.432463 0.017 Uiso 1 1 calc R . . . .
C11 C 0.37539(10) 0.7587(5) 0.7504(3) 0.0147(5) Uani 1 1 d . . . . .
C8 C 0.27462(10) 1.0027(5) 0.7216(3) 0.0191(5) Uani 1 1 d . . . . .
H8 H 0.240111 1.088804 0.713352 0.023 Uiso 1 1 calc R . . . .
C1 C 0.41199(10) 0.2685(5) 0.2195(3) 0.0161(5) Uani 1 1 d . . . . .
C12 C 0.42038(10) 0.4651(5) 0.6159(3) 0.0139(5) Uani 1 1 d . . . . .
C9 C 0.30979(10) 1.0728(5) 0.8337(3) 0.0204(5) Uani 1 1 d . . . . .
H9 H 0.298554 1.205357 0.899443 0.024 Uiso 1 1 calc R . . . .
C7 C 0.28913(10) 0.8107(5) 0.6225(3) 0.0165(5) Uani 1 1 d . . . . .
H7 H 0.264952 0.764012 0.547479 0.020 Uiso 1 1 calc R . . . .
C10 C 0.36056(10) 0.9525(5) 0.8505(3) 0.0187(5) Uani 1 1 d . . . . .
H10 H 0.384260 0.999480 0.926548 0.022 Uiso 1 1 calc R . . . .
C14 C 0.44200(10) 0.0981(5) 0.4540(3) 0.0160(5) Uani 1 1 d . . . . .
H14A H 0.471584 0.012944 0.398289 0.019 Uiso 1 1 calc R . . . .
H14B H 0.422766 -0.042081 0.508510 0.019 Uiso 1 1 calc R . . . .
C13 C 0.46646(10) 0.3013(5) 0.5558(3) 0.0154(5) Uani 1 1 d . . . . .
H13 H 0.486591 0.208837 0.634041 0.019 Uiso 1 1 calc R . . . .
C3 C 0.33907(10) 0.5583(5) 0.2939(3) 0.0179(5) Uani 1 1 d . . . . .
H3A H 0.298773 0.567458 0.282819 0.021 Uiso 1 1 calc R . . . .
H3B H 0.353290 0.739524 0.312275 0.021 Uiso 1 1 calc R . . . .
C2 C 0.36579(11) 0.4381(6) 0.1617(3) 0.0217(5) Uani 1 1 d . . . . .
H2B H 0.339241 0.328198 0.108038 0.026 Uiso 1 1 calc R . . . .
H2C H 0.380114 0.579271 0.098476 0.026 Uiso 1 1 calc R . . . .
H2A H 0.4511(13) 0.612(8) 0.803(4) 0.043(11) Uiso 1 1 d 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
O2 H2 0.86(4) . ?
O2 C13 1.436(3) . ?
O1 C1 1.237(3) . ?
N2 C11 1.377(3) . ?
N2 C12 1.376(3) . ?
N2 H2A 0.92(2) . ?
N1 C4 1.472(3) . ?
N1 C1 1.336(3) . ?
N1 C14 1.461(3) . ?
C5 C6 1.428(3) . ?
C5 C4 1.493(3) . ?
C5 C12 1.374(3) . ?
C6 C11 1.418(3) . ?
C6 C7 1.408(3) . ?
C4 H4 1.0000 . ?
C4 C3 1.550(3) . ?
C11 C10 1.403(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.405(4) . ?
C8 C7 1.388(4) . ?
C1 C2 1.515(3) . ?
C12 C13 1.504(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(4) . ?
C7 H7 0.9500 . ?
C10 H10 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.522(4) . ?
C13 H13 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.530(4) . ?
C2 H2B 0.9900 . ?
C2 H2C 0.9900 . ?

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
C13 O2 H2 109.5 . . ?
C11 N2 H2A 125(3) . . ?
C12 N2 C11 108.5(2) . . ?
C12 N2 H2A 126(3) . . ?
C1 N1 C4 114.7(2) . . ?
C1 N1 C14 124.7(2) . . ?
C14 N1 C4 120.0(2) . . ?
C6 C5 C4 130.2(2) . . ?
C12 C5 C6 107.0(2) . . ?
C12 C5 C4 122.8(2) . . ?
C11 C6 C5 106.6(2) . . ?
C7 C6 C5 133.9(2) . . ?
C7 C6 C11 119.4(2) . . ?
N1 C4 C5 109.0(2) . . ?
N1 C4 H4 110.0 . . ?
N1 C4 C3 102.62(18) . . ?
C5 C4 H4 110.0 . . ?
C5 C4 C3 115.0(2) . . ?
C3 C4 H4 110.0 . . ?
N2 C11 C6 108.0(2) . . ?
N2 C11 C10 129.7(2) . . ?
C10 C11 C6 122.2(2) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C7 C8 C9 121.5(2) . . ?
O1 C1 N1 125.3(2) . . ?
O1 C1 C2 126.2(2) . . ?
N1 C1 C2 108.5(2) . . ?
N2 C12 C13 125.1(2) . . ?
C5 C12 N2 110.0(2) . . ?
C5 C12 C13 124.8(2) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.5(2) . . ?
C10 C9 H9 119.3 . . ?
C6 C7 H7 120.8 . . ?
C8 C7 C6 118.3(2) . . ?
C8 C7 H7 120.8 . . ?
C11 C10 H10 121.4 . . ?
C9 C10 C11 117.1(2) . . ?
C9 C10 H10 121.4 . . ?
N1 C14 H14A 109.7 . . ?
N1 C14 H14B 109.7 . . ?
N1 C14 C13 109.70(19) . . ?
H14A C14 H14B 108.2 . . ?
C13 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
O2 C13 C12 111.70(19) . . ?
O2 C13 C14 106.5(2) . . ?
O2 C13 H13 110.2 . . ?
C12 C13 C14 108.1(2) . . ?
C12 C13 H13 110.2 . . ?
C14 C13 H13 110.2 . . ?
C4 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C2 C3 C4 104.47(19) . . ?
C2 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
C1 C2 C3 104.3(2) . . ?
C1 C2 H2B 110.9 . . ?
C1 C2 H2C 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C3 C2 H2C 110.9 . . ?
H2B C2 H2C 108.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
