# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_fisk-09re
_database_code_depnum_ccdc_archive 'CCDC 1825913'
loop_
_audit_author_name
_audit_author_address
'rajni kant' 'university of jammu'
_audit_update_record             
;
2018-02-26 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 N2 O3'
_chemical_formula_sum            'C20 H18 N2 O3'
_chemical_formula_weight         334.36

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   p-1

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

_cell_length_a                   8.5337(13)
_cell_length_b                   10.2008(13)
_cell_length_c                   11.672(2)
_cell_angle_alpha                90.880(14)
_cell_angle_beta                 110.076(16)
_cell_angle_gamma                114.477(14)
_cell_volume                     853.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1519
_cell_measurement_theta_min      4.0010
_cell_measurement_theta_max      26.2050

_exptl_crystal_description       block
_exptl_crystal_colour            transparent
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.60609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'crys Alis RED'

_exptl_special_details           
;
 CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.1049
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5456
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0900
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.68
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2988
_reflns_number_gt                1859
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro,Oxford Diff.Ltd,Ver 1.171.34.40'
_computing_cell_refinement       'CrysAlisPro,Oxford Diff.Ltd,Ver 1.171.34.40'
_computing_data_reduction        'CrysAlisPro,Oxford Diff.Ltd,Ver 1.171.34.40'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'PLATON(Spek,2009)& PARST(Nardelli,1995)'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0136(15)
_refine_ls_number_reflns         2988
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1945
_refine_ls_R_factor_gt           0.1639
_refine_ls_wR_factor_ref         0.4779
_refine_ls_wR_factor_gt          0.4595
_refine_ls_goodness_of_fit_ref   1.616
_refine_ls_restrained_S_all      1.616
_refine_ls_shift/su_max          0.886
_refine_ls_shift/su_mean         0.012

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C20 C -0.519(4) 0.844(3) -0.599(4) 0.45(4) Uani 1 1 d . . .
H20A H -0.4141 0.9021 -0.6194 0.675 Uiso 1 1 calc R . .
H20B H -0.5341 0.9057 -0.5446 0.675 Uiso 1 1 calc R . .
H20C H -0.6297 0.8009 -0.6735 0.675 Uiso 1 1 calc R . .
O2 O 0.2772(6) 0.4330(5) 0.0475(4) 0.0521(14) Uani 1 1 d . . .
H2 H 0.3781 0.4943 0.0495 0.078 Uiso 1 1 calc R . .
O1 O 0.3985(7) 0.3038(6) -0.1171(5) 0.0586(15) Uani 1 1 d . . .
N2 N 0.0104(8) 0.5719(7) -0.2981(5) 0.0516(16) Uani 1 1 d . . .
N1 N 0.1072(8) 0.1227(6) -0.1578(5) 0.0489(15) Uani 1 1 d . . .
C8 C 0.1619(8) 0.3565(7) -0.0759(6) 0.0426(16) Uani 1 1 d . . .
C6 C -0.0485(9) 0.1058(8) -0.1324(7) 0.0480(17) Uani 1 1 d . . .
C7 C 0.2443(9) 0.2640(7) -0.1176(6) 0.0437(16) Uani 1 1 d . . .
C14 C -0.1219(10) 0.6200(8) -0.3697(6) 0.0486(17) Uani 1 1 d . . .
C10 C 0.1377(9) 0.4562(7) -0.1659(6) 0.0451(16) Uani 1 1 d . . .
C5 C -0.2085(10) -0.0227(8) -0.1495(7) 0.0580(19) Uani 1 1 d . . .
H5 H -0.2244 -0.1130 -0.1826 0.070 Uiso 1 1 calc R . .
C11 C -0.0249(9) 0.4631(8) -0.2297(6) 0.0485(17) Uani 1 1 d . . .
H11 H -0.1404 0.4039 -0.2272 0.058 Uiso 1 1 calc R . .
C15 C -0.2576(10) 0.6174(9) -0.3289(7) 0.058(2) Uani 1 1 d . . .
H15 H -0.2643 0.5820 -0.2570 0.069 Uiso 1 1 calc R . .
C12 C 0.1945(10) 0.6334(9) -0.2784(7) 0.057(2) Uani 1 1 d . . .
H12 H 0.2539 0.7096 -0.3142 0.069 Uiso 1 1 calc R . .
C9 C 0.1258(12) 0.0036(9) -0.2135(9) 0.066(2) Uani 1 1 d . . .
H9A H 0.2479 0.0401 -0.2157 0.100 Uiso 1 1 calc R . .
H9B H 0.0334 -0.0350 -0.2965 0.100 Uiso 1 1 calc R . .
H9C H 0.1083 -0.0726 -0.1651 0.100 Uiso 1 1 calc R . .
C1 C -0.0217(9) 0.2401(7) -0.0798(6) 0.0423(16) Uani 1 1 d . . .
C16 C -0.3829(12) 0.6679(10) -0.3959(8) 0.066(2) Uani 1 1 d . . .
H16 H -0.4737 0.6663 -0.3683 0.079 Uiso 1 1 calc R . .
C2 C -0.1535(9) 0.2496(8) -0.0440(7) 0.0513(18) Uani 1 1 d . . .
H2A H -0.1356 0.3396 -0.0087 0.062 Uiso 1 1 calc R . .
C13 C 0.2776(10) 0.5649(8) -0.1974(8) 0.0570(19) Uani 1 1 d . . .
H13 H 0.4030 0.5857 -0.1682 0.068 Uiso 1 1 calc R . .
C4 C -0.3409(11) -0.0108(10) -0.1159(8) 0.070(2) Uani 1 1 d . . .
H4 H -0.4514 -0.0942 -0.1300 0.084 Uiso 1 1 calc R . .
C19 C -0.1204(12) 0.6677(10) -0.4795(8) 0.068(2) Uani 1 1 d . . .
H19 H -0.0369 0.6634 -0.5119 0.082 Uiso 1 1 calc R . .
C17 C -0.3754(13) 0.7203(10) -0.5024(9) 0.073(2) Uani 1 1 d . . .
C18 C -0.2423(13) 0.7213(11) -0.5400(9) 0.079(3) Uani 1 1 d . . .
H18 H -0.2332 0.7602 -0.6103 0.094 Uiso 1 1 calc R . .
O3 O -0.4993(12) 0.7709(11) -0.5597(10) 0.131(3) Uani 1 1 d . . .
C3 C -0.3155(10) 0.1227(9) -0.0610(8) 0.060(2) Uani 1 1 d . . .
H3 H -0.4059 0.1272 -0.0360 0.072 Uiso 1 1 calc R . .


_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
C20 O3 0.93(2) . ?
C20 H20A 0.9591 . ?
C20 H20B 0.9591 . ?
C20 H20C 0.9590 . ?
O2 C8 1.417(8) . ?
O2 H2 0.8200 . ?
O1 C7 1.204(7) . ?
N2 C12 1.358(9) . ?
N2 C11 1.370(8) . ?
N2 C14 1.427(9) . ?
N1 C7 1.367(9) . ?
N1 C6 1.401(8) . ?
N1 C9 1.461(9) . ?
C8 C10 1.496(9) . ?
C8 C1 1.508(9) . ?
C8 C7 1.547(9) . ?
C6 C1 1.387(10) . ?
C6 C5 1.395(10) . ?
C14 C19 1.380(11) . ?
C14 C15 1.386(10) . ?
C10 C11 1.363(9) . ?
C10 C13 1.417(9) . ?
C5 C4 1.364(10) . ?
C5 H5 0.9300 . ?
C11 H11 0.9300 . ?
C15 C16 1.384(10) . ?
C15 H15 0.9300 . ?
C12 C13 1.362(10) . ?
C12 H12 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C1 C2 1.364(9) . ?
C16 C17 1.372(13) . ?
C16 H16 0.9300 . ?
C2 C3 1.395(10) . ?
C2 H2A 0.9300 . ?
C13 H13 0.9300 . ?
C4 C3 1.395(11) . ?
C4 H4 0.9300 . ?
C19 C18 1.363(11) . ?
C19 H19 0.9300 . ?
C17 C18 1.347(12) . ?
C17 O3 1.345(10) . ?
C18 H18 0.9300 . ?
C3 H3 0.9300 . ?

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
O3 C20 H20A 109.4 . . ?
O3 C20 H20B 108.9 . . ?
H20A C20 H20B 109.7 . . ?
O3 C20 H20C 109.7 . . ?
H20A C20 H20C 109.7 . . ?
H20B C20 H20C 109.4 . . ?
C8 O2 H2 109.5 . . ?
C12 N2 C11 108.6(5) . . ?
C12 N2 C14 126.0(6) . . ?
C11 N2 C14 125.2(6) . . ?
C7 N1 C6 111.4(5) . . ?
C7 N1 C9 124.0(6) . . ?
C6 N1 C9 124.6(6) . . ?
O2 C8 C10 112.9(5) . . ?
O2 C8 C1 109.9(5) . . ?
C10 C8 C1 112.5(5) . . ?
O2 C8 C7 109.9(5) . . ?
C10 C8 C7 109.1(5) . . ?
C1 C8 C7 102.0(5) . . ?
C1 C6 C5 121.5(6) . . ?
C1 C6 N1 110.0(6) . . ?
C5 C6 N1 128.4(6) . . ?
O1 C7 N1 124.4(6) . . ?
O1 C7 C8 128.4(6) . . ?
N1 C7 C8 107.3(5) . . ?
C19 C14 C15 118.7(7) . . ?
C19 C14 N2 122.0(6) . . ?
C15 C14 N2 119.3(6) . . ?
C11 C10 C13 106.8(6) . . ?
C11 C10 C8 125.7(6) . . ?
C13 C10 C8 127.4(6) . . ?
C4 C5 C6 117.3(7) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
C10 C11 N2 108.6(6) . . ?
C10 C11 H11 125.7 . . ?
N2 C11 H11 125.7 . . ?
C16 C15 C14 119.6(8) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
N2 C12 C13 108.7(6) . . ?
N2 C12 H12 125.7 . . ?
C13 C12 H12 125.7 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C1 C6 120.3(6) . . ?
C2 C1 C8 131.1(6) . . ?
C6 C1 C8 108.5(5) . . ?
C17 C16 C15 121.0(8) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C1 C2 C3 119.2(7) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 H2A 120.4 . . ?
C12 C13 C10 107.3(6) . . ?
C12 C13 H13 126.4 . . ?
C10 C13 H13 126.4 . . ?
C5 C4 C3 122.0(7) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C18 C19 C14 119.5(8) . . ?
C18 C19 H19 120.3 . . ?
C14 C19 H19 120.3 . . ?
C18 C17 O3 124.9(9) . . ?
C18 C17 C16 118.1(8) . . ?
O3 C17 C16 117.0(9) . . ?
C17 C18 C19 122.9(8) . . ?
C17 C18 H18 118.6 . . ?
C19 C18 H18 118.6 . . ?
C20 O3 C17 147(3) . . ?
C4 C3 C2 119.5(7) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?

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
C7 N1 C6 C1 3.3(8) . . . . ?
C9 N1 C6 C1 -179.9(7) . . . . ?
C7 N1 C6 C5 -174.2(7) . . . . ?
C9 N1 C6 C5 2.6(12) . . . . ?
C6 N1 C7 O1 172.2(6) . . . . ?
C9 N1 C7 O1 -4.6(11) . . . . ?
C6 N1 C7 C8 -8.0(7) . . . . ?
C9 N1 C7 C8 175.2(6) . . . . ?
O2 C8 C7 O1 -54.6(8) . . . . ?
C10 C8 C7 O1 69.7(8) . . . . ?
C1 C8 C7 O1 -171.1(6) . . . . ?
O2 C8 C7 N1 125.7(5) . . . . ?
C10 C8 C7 N1 -110.1(6) . . . . ?
C1 C8 C7 N1 9.1(7) . . . . ?
C12 N2 C14 C19 39.5(11) . . . . ?
C11 N2 C14 C19 -146.1(8) . . . . ?
C12 N2 C14 C15 -141.2(8) . . . . ?
C11 N2 C14 C15 33.1(10) . . . . ?
O2 C8 C10 C11 -113.6(7) . . . . ?
C1 C8 C10 C11 11.4(9) . . . . ?
C7 C8 C10 C11 123.9(7) . . . . ?
O2 C8 C10 C13 63.3(9) . . . . ?
C1 C8 C10 C13 -171.7(6) . . . . ?
C7 C8 C10 C13 -59.2(9) . . . . ?
C1 C6 C5 C4 1.9(11) . . . . ?
N1 C6 C5 C4 179.2(7) . . . . ?
C13 C10 C11 N2 -0.3(8) . . . . ?
C8 C10 C11 N2 177.2(6) . . . . ?
C12 N2 C11 C10 0.3(8) . . . . ?
C14 N2 C11 C10 -174.9(6) . . . . ?
C19 C14 C15 C16 -2.6(11) . . . . ?
N2 C14 C15 C16 178.1(7) . . . . ?
C11 N2 C12 C13 -0.2(8) . . . . ?
C14 N2 C12 C13 175.0(7) . . . . ?
C5 C6 C1 C2 -0.4(11) . . . . ?
N1 C6 C1 C2 -178.2(6) . . . . ?
C5 C6 C1 C8 -179.2(6) . . . . ?
N1 C6 C1 C8 3.0(8) . . . . ?
O2 C8 C1 C2 57.5(9) . . . . ?
C10 C8 C1 C2 -69.1(9) . . . . ?
C7 C8 C1 C2 174.1(7) . . . . ?
O2 C8 C1 C6 -123.8(6) . . . . ?
C10 C8 C1 C6 109.5(6) . . . . ?
C7 C8 C1 C6 -7.3(7) . . . . ?
C14 C15 C16 C17 0.2(12) . . . . ?
C6 C1 C2 C3 -0.1(10) . . . . ?
C8 C1 C2 C3 178.5(7) . . . . ?
N2 C12 C13 C10 0.0(9) . . . . ?
C11 C10 C13 C12 0.2(9) . . . . ?
C8 C10 C13 C12 -177.2(7) . . . . ?
C6 C5 C4 C3 -3.0(12) . . . . ?
C15 C14 C19 C18 4.9(13) . . . . ?
N2 C14 C19 C18 -175.8(7) . . . . ?
C15 C16 C17 C18 0.0(13) . . . . ?
C15 C16 C17 O3 -178.2(8) . . . . ?
O3 C17 C18 C19 -179.5(10) . . . . ?
C16 C17 C18 C19 2.5(15) . . . . ?
C14 C19 C18 C17 -5.0(15) . . . . ?
C18 C17 O3 C20 -42(5) . . . . ?
C16 C17 O3 C20 136(5) . . . . ?
C5 C4 C3 C2 2.6(13) . . . . ?
C1 C2 C3 C4 -1.0(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.133
####################################################################### 
# 
# 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_exp_518_indresh-01
_database_code_depnum_ccdc_archive 'CCDC 1973218'
loop_
_audit_author_name
_audit_author_address
'Krishnan Rangan'
;BITS Pilani Hyderabad Campus
India
;
_audit_update_record             
;
2019-12-20 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_audit_creation_date             2019-12-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 N2 O2'
_chemical_formula_sum            'C16 H18 N2 O2'
_chemical_formula_weight         270.32
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   10.8918(2)
_cell_length_b                   10.9673(2)
_cell_length_c                   11.9061(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.324(2)
_cell_angle_gamma                90
_cell_volume                     1389.45(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4826
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      79.4160
_cell_measurement_theta_min      5.5070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7404
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.954
_diffrn_reflns_theta_min         4.155
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     17.00  45.00   0.50    1.92    --    0.00  57.00  60.00   56
  2  ω    -19.00  89.00   0.50    1.92    --    0.00  37.00-150.00  216
  3  ω    -31.00  -5.00   0.50    1.92    --    0.00 -57.00 -30.00   52
  4  ω    -88.00 -56.00   0.50    1.92    --    0.00 -57.00 -30.00   64
  5  ω     98.00 134.00   0.50    7.68    --  107.20 -15.00  30.00   72
  6  ω    105.00 194.00   0.50    7.68    --  107.20  45.00   0.00  178
  7  ω     19.00 115.00   0.50    7.68    --  107.20 -45.00  90.00  192
  8  ω     19.00  63.00   0.50    7.68    --  107.20 -15.00  30.00   88
  9  ω     24.00  81.00   0.50    7.68    --  107.20 -30.00-120.00  114
 10  ω     36.00 119.00   0.50    7.68    --  107.20 -61.00  90.00  166
 11  ω     18.00  45.00   0.50    7.68    --  107.20 -30.00 -60.00   54
 12  ω     80.00 105.00   0.50    7.68    --  107.20 -30.00 -60.00   50
 13  ω     94.00 138.00   0.50    7.68    --  107.20 -77.00-120.00   88
 14  ω     30.00  89.00   0.50    7.68    --  107.20 -77.00-120.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0926075000
_diffrn_orient_matrix_UB_12      -0.0370575000
_diffrn_orient_matrix_UB_13      0.0753240000
_diffrn_orient_matrix_UB_21      0.0843607000
_diffrn_orient_matrix_UB_22      0.0625470000
_diffrn_orient_matrix_UB_23      0.1043654000
_diffrn_orient_matrix_UB_31      -0.0724995000
_diffrn_orient_matrix_UB_32      0.1202494000
_diffrn_orient_matrix_UB_33      -0.0311843000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2675
_reflns_number_total             2934
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 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 (Sheldrick, 2015)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2934
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.056
_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)+(0.0542P)²+0.6332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1088
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C2(H2A), C10(H10), C12(H12), C11(H11), C3(H3)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O2 O 0.00757(8) 0.61868(8) 0.15457(7) 0.01446(19) Uani 1 1 d . . . . .
H2 H -0.000912 0.617240 0.084473 0.022 Uiso 1 1 calc GR . . . .
O1 O 0.04504(8) 0.36519(8) 0.08367(7) 0.0173(2) Uani 1 1 d . . . . .
N1 N 0.08653(9) 0.35009(9) 0.28072(9) 0.0148(2) Uani 1 1 d . . . . .
H1 H 0.073490 0.273237 0.286567 0.018 Uiso 1 1 calc R . . . .
N2 N 0.41723(9) 0.65852(10) 0.15514(9) 0.0159(2) Uani 1 1 d . . . . .
C1 C 0.11968(10) 0.43035(11) 0.37535(10) 0.0136(2) Uani 1 1 d . . . . .
C6 C 0.13254(10) 0.54836(11) 0.33567(10) 0.0128(2) Uani 1 1 d . . . . .
C8 C 0.07796(10) 0.40969(11) 0.17982(10) 0.0129(2) Uani 1 1 d . . . . .
C9 C 0.23073(11) 0.57823(10) 0.16434(10) 0.0132(2) Uani 1 1 d . . . . .
C7 C 0.11401(10) 0.54542(10) 0.20663(10) 0.0125(2) Uani 1 1 d . . . . .
C4 C 0.17547(11) 0.61869(12) 0.53018(10) 0.0174(3) Uani 1 1 d . . . . .
H4 H 0.193410 0.681777 0.583358 0.021 Uiso 1 1 calc R . . . .
C5 C 0.15936(11) 0.64389(11) 0.41306(10) 0.0149(2) Uani 1 1 d . . . . .
H5 H 0.166479 0.723186 0.387518 0.018 Uiso 1 1 calc R . . . .
C2 C 0.13651(11) 0.40276(11) 0.49088(10) 0.0166(3) Uani 1 1 d . . . . .
H2A H 0.129278 0.323341 0.516074 0.020 Uiso 1 1 calc R . . . .
C10 C 0.25228(11) 0.55842(11) 0.05198(10) 0.0161(3) Uani 1 1 d . . . . .
H10 H 0.198862 0.518585 -0.008213 0.019 Uiso 1 1 calc R . . . .
C12 C 0.33443(11) 0.63983(11) 0.22544(10) 0.0143(2) Uani 1 1 d . . . . .
H12 H 0.346099 0.664520 0.301709 0.017 Uiso 1 1 calc R . . . .
C11 C 0.36659(11) 0.60912(12) 0.04924(10) 0.0170(3) Uani 1 1 d . . . . .
H11 H 0.403935 0.609974 -0.014085 0.020 Uiso 1 1 calc R . . . .
C3 C 0.16489(11) 0.49978(12) 0.56800(10) 0.0180(3) Uani 1 1 d . . . . .
H3 H 0.177015 0.484635 0.646458 0.022 Uiso 1 1 calc R . . . .
C13 C 0.53764(11) 0.72798(12) 0.18195(11) 0.0189(3) Uani 1 1 d . . . . .
C14 C 0.63901(12) 0.65107(13) 0.14479(13) 0.0250(3) Uani 1 1 d . . . . .
H14A H 0.643919 0.572894 0.181750 0.038 Uiso 1 1 calc GR . . . .
H14B H 0.718618 0.691727 0.166373 0.038 Uiso 1 1 calc GR . . . .
H14C H 0.618172 0.640277 0.062904 0.038 Uiso 1 1 calc GR . . . .
C16 C 0.51979(13) 0.84872(13) 0.11644(13) 0.0268(3) Uani 1 1 d . . . . .
H16A H 0.493805 0.832869 0.035545 0.040 Uiso 1 1 calc GR . . . .
H16B H 0.597677 0.892883 0.131079 0.040 Uiso 1 1 calc GR . . . .
H16C H 0.456660 0.896260 0.141540 0.040 Uiso 1 1 calc GR . . . .
C15 C 0.57517(14) 0.75232(16) 0.31051(12) 0.0304(3) Uani 1 1 d . . . . .
H15A H 0.513202 0.803387 0.333357 0.046 Uiso 1 1 calc GR . . . .
H15B H 0.655302 0.792487 0.327822 0.046 Uiso 1 1 calc GR . . . .
H15C H 0.580679 0.676433 0.351471 0.046 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
O2 H2 0.8200 . ?
O2 C7 1.4377(13) . ?
O1 C8 1.2256(14) . ?
N1 H1 0.8600 . ?
N1 C1 1.4145(15) . ?
N1 C8 1.3532(15) . ?
N2 C12 1.3704(15) . ?
N2 C11 1.3750(15) . ?
N2 C13 1.4911(15) . ?
C1 C6 1.3950(16) . ?
C1 C2 1.3819(16) . ?
C6 C7 1.5066(15) . ?
C6 C5 1.3847(16) . ?
C8 C7 1.5552(16) . ?
C9 C7 1.5075(15) . ?
C9 C10 1.4234(16) . ?
C9 C12 1.3822(16) . ?
C4 H4 0.9300 . ?
C4 C5 1.3954(17) . ?
C4 C3 1.3925(18) . ?
C5 H5 0.9300 . ?
C2 H2A 0.9300 . ?
C2 C3 1.3964(18) . ?
C10 H10 0.9300 . ?
C10 C11 1.3703(17) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C3 H3 0.9300 . ?
C13 C14 1.5280(18) . ?
C13 C16 1.5280(19) . ?
C13 C15 1.5212(18) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
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
C7 O2 H2 109.5 . . ?
C1 N1 H1 124.3 . . ?
C8 N1 H1 124.3 . . ?
C8 N1 C1 111.35(10) . . ?
C12 N2 C11 108.27(10) . . ?
C12 N2 C13 127.52(10) . . ?
C11 N2 C13 124.05(10) . . ?
C6 C1 N1 109.55(10) . . ?
C2 C1 N1 127.85(11) . . ?
C2 C1 C6 122.59(11) . . ?
C1 C6 C7 108.92(10) . . ?
C5 C6 C1 119.92(11) . . ?
C5 C6 C7 131.15(11) . . ?
O1 C8 N1 126.01(11) . . ?
O1 C8 C7 125.70(10) . . ?
N1 C8 C7 108.28(10) . . ?
C10 C9 C7 126.69(11) . . ?
C12 C9 C7 126.41(10) . . ?
C12 C9 C10 106.81(10) . . ?
O2 C7 C6 110.36(9) . . ?
O2 C7 C8 107.54(9) . . ?
O2 C7 C9 112.49(9) . . ?
C6 C7 C8 101.69(9) . . ?
C6 C7 C9 113.36(9) . . ?
C9 C7 C8 110.73(9) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.48(11) . . ?
C6 C5 C4 118.61(11) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C1 C2 H2A 121.6 . . ?
C1 C2 C3 116.83(11) . . ?
C3 C2 H2A 121.6 . . ?
C9 C10 H10 126.5 . . ?
C11 C10 C9 107.06(11) . . ?
C11 C10 H10 126.5 . . ?
N2 C12 C9 108.79(10) . . ?
N2 C12 H12 125.6 . . ?
C9 C12 H12 125.6 . . ?
N2 C11 H11 125.5 . . ?
C10 C11 N2 109.07(10) . . ?
C10 C11 H11 125.5 . . ?
C4 C3 C2 121.53(11) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
N2 C13 C14 108.23(10) . . ?
N2 C13 C16 108.86(10) . . ?
N2 C13 C15 109.89(10) . . ?
C16 C13 C14 110.59(11) . . ?
C15 C13 C14 109.43(11) . . ?
C15 C13 C16 109.82(12) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1_$1 0.82 1.97 2.7770(12) 169.9 3_565


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.605
_oxdiff_exptl_absorpt_empirical_full_min 0.817
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate and Hexane'
####################################################################### 
# 
# 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_exp_534_indresh-ap-ch2ph-fr-nh
_database_code_depnum_ccdc_archive 'CCDC 1973219'
loop_
_audit_author_name
_audit_author_address
'Krishnan Rangan'
;BITS Pilani Hyderabad Campus
India
;
_audit_update_record             
;
2019-12-20 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_audit_creation_date             2019-12-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 N2 O2'
_chemical_formula_sum            'C19 H16 N2 O2'
_chemical_formula_weight         304.34
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.2879(2)
_cell_length_b                   7.27320(10)
_cell_length_c                   19.0032(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.460(2)
_cell_angle_gamma                90
_cell_volume                     1517.29(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5180
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      79.2800
_cell_measurement_theta_min      7.2710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7899
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.382
_diffrn_reflns_theta_min         4.178
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     12.00  65.00   0.50    1.89    --    0.00  77.00  90.00  106
  2  ω    -19.00  37.00   0.50    1.89    --    0.00  37.00-150.00  112
  3  ω    -50.00  32.00   0.50    1.89    --    0.00 -82.00   0.00  164
  4  ω     44.00  86.00   0.50    1.89    --    0.00  37.00-150.00   84
  5  ω     24.00 115.00   0.50    7.56    --  107.20 -30.00-120.00  182
  6  ω     24.00  89.00   0.50    7.56    --  107.20 -45.00  30.00  130
  7  ω     21.00 125.00   0.50    7.56    --  107.20 -30.00  30.00  208
  8  ω     95.00 166.00   0.50    7.56    --  107.20  30.00 150.00  142
  9  ω     25.00  91.00   0.50    7.56    --  107.20 -45.00-120.00  132
 10  ω    171.00 196.00   0.50    7.56    --  107.20  30.00 -60.00   50
 11  ω     83.00 195.00   0.50    7.56    --  107.20  61.00   0.00  224
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0594237000
_diffrn_orient_matrix_UB_12      0.0715754000
_diffrn_orient_matrix_UB_13      -0.0598859000
_diffrn_orient_matrix_UB_21      0.1126954000
_diffrn_orient_matrix_UB_22      -0.1201239000
_diffrn_orient_matrix_UB_23      0.0299018000
_diffrn_orient_matrix_UB_31      -0.0586145000
_diffrn_orient_matrix_UB_32      -0.1592354000
_diffrn_orient_matrix_UB_33      -0.0497169000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2906
_reflns_number_total             3183
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 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 (Sheldrick, 2015)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.082
_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)+(0.0539P)²+0.5825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1213
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2A), C12(H12), C10(H10), C15(H15), C16(H16), C17(H17), C19(H19), C11(H11),
  C18(H18), C5(H5), C2(H2B), C4(H4), C3(H3)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O2 O 0.91616(9) 0.65313(12) 0.57958(5) 0.0267(2) Uani 1 1 d . . . . .
H2 H 0.978062 0.604066 0.572958 0.040 Uiso 1 1 calc GR . . . .
O1 O 0.86298(9) 0.47616(13) 0.43403(5) 0.0295(2) Uani 1 1 d . . . . .
N1 N 0.67753(11) 0.59297(16) 0.43977(7) 0.0305(3) Uani 1 1 d . . . . .
N2 N 0.87440(13) 0.04873(17) 0.60082(7) 0.0365(3) Uani 1 1 d . . . . .
H2A H 0.898870 -0.060560 0.594275 0.044 Uiso 1 1 calc R . . . .
C8 C 0.79075(12) 0.52785(17) 0.46904(7) 0.0251(3) Uani 1 1 d . . . . .
C7 C 0.81339(12) 0.53640(17) 0.55227(7) 0.0250(3) Uani 1 1 d . . . . .
C9 C 0.82842(13) 0.34466(18) 0.58360(7) 0.0270(3) Uani 1 1 d . . . . .
C6 C 0.69958(13) 0.63197(18) 0.56179(9) 0.0321(3) Uani 1 1 d . . . . .
C1 C 0.62220(13) 0.65991(18) 0.49422(9) 0.0349(3) Uani 1 1 d . . . . .
C14 C 0.64483(14) 0.80524(19) 0.33520(8) 0.0332(3) Uani 1 1 d . . . . .
C12 C 0.87305(14) 0.19337(19) 0.55514(8) 0.0321(3) Uani 1 1 d . . . . .
H12 H 0.898170 0.190171 0.511892 0.039 Uiso 1 1 calc R . . . .
C10 C 0.80142(16) 0.2857(2) 0.64957(8) 0.0385(4) Uani 1 1 d . . . . .
H10 H 0.769361 0.357930 0.681023 0.046 Uiso 1 1 calc R . . . .
C15 C 0.73819(15) 0.9194(2) 0.37030(8) 0.0350(3) Uani 1 1 d . . . . .
H15 H 0.788730 0.882343 0.413916 0.042 Uiso 1 1 calc R . . . .
C16 C 0.75697(17) 1.0888(2) 0.34085(8) 0.0396(4) Uani 1 1 d . . . . .
H16 H 0.819906 1.164602 0.364803 0.047 Uiso 1 1 calc R . . . .
C17 C 0.68239(18) 1.1449(2) 0.27612(8) 0.0411(4) Uani 1 1 d . . . . .
H17 H 0.694764 1.258549 0.256573 0.049 Uiso 1 1 calc R . . . .
C19 C 0.57031(16) 0.8640(2) 0.27013(8) 0.0393(4) Uani 1 1 d . . . . .
H19 H 0.506703 0.789419 0.246148 0.047 Uiso 1 1 calc R . . . .
C13 C 0.62846(15) 0.6140(2) 0.36267(9) 0.0398(4) Uani 1 1 d . . . . .
H13A H 0.542259 0.584765 0.351640 0.048 Uiso 1 1 calc R . . . .
H13B H 0.668090 0.526420 0.337183 0.048 Uiso 1 1 calc R . . . .
C11 C 0.83110(17) 0.1040(2) 0.65828(9) 0.0408(4) Uani 1 1 d . . . . .
H11 H 0.823048 0.030525 0.696956 0.049 Uiso 1 1 calc R . . . .
C18 C 0.58986(17) 1.0324(2) 0.24067(8) 0.0428(4) Uani 1 1 d . . . . .
H18 H 0.540184 1.069394 0.196768 0.051 Uiso 1 1 calc R . . . .
C5 C 0.66523(17) 0.6913(2) 0.62331(11) 0.0444(4) Uani 1 1 d . . . . .
H5 H 0.716019 0.675105 0.669011 0.053 Uiso 1 1 calc R . . . .
C2 C 0.50935(15) 0.7430(2) 0.48510(13) 0.0505(5) Uani 1 1 d . . . . .
H2B H 0.458931 0.760210 0.439355 0.061 Uiso 1 1 calc R . . . .
C4 C 0.5512(2) 0.7766(2) 0.61445(16) 0.0638(7) Uani 1 1 d . . . . .
H4 H 0.526471 0.818849 0.654968 0.077 Uiso 1 1 calc R . . . .
C3 C 0.47481(18) 0.7992(2) 0.54668(17) 0.0637(7) Uani 1 1 d . . . . .
H3 H 0.398821 0.853156 0.542569 0.076 Uiso 1 1 calc R . . . .


_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 0.8200 . ?
O2 C7 1.4337(16) . ?
O1 C8 1.2252(16) . ?
N1 C8 1.3550(17) . ?
N1 C1 1.414(2) . ?
N1 C13 1.449(2) . ?
N2 H2A 0.8600 . ?
N2 C12 1.3617(18) . ?
N2 C11 1.357(2) . ?
C8 C7 1.5435(18) . ?
C7 C9 1.5104(18) . ?
C7 C6 1.5082(18) . ?
C9 C12 1.3726(19) . ?
C9 C10 1.4235(19) . ?
C6 C1 1.390(2) . ?
C6 C5 1.384(2) . ?
C1 C2 1.384(2) . ?
C14 C15 1.385(2) . ?
C14 C19 1.391(2) . ?
C14 C13 1.512(2) . ?
C12 H12 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.364(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.386(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C11 H11 0.9300 . ?
C18 H18 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.404(3) . ?
C2 H2B 0.9300 . ?
C2 C3 1.379(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.382(4) . ?
C3 H3 0.9300 . ?

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 O2 H2 109.5 . . ?
C8 N1 C1 110.80(12) . . ?
C8 N1 C13 123.64(13) . . ?
C1 N1 C13 125.02(13) . . ?
C12 N2 H2A 125.3 . . ?
C11 N2 H2A 125.3 . . ?
C11 N2 C12 109.37(12) . . ?
O1 C8 N1 124.59(13) . . ?
O1 C8 C7 126.60(12) . . ?
N1 C8 C7 108.78(11) . . ?
O2 C7 C8 108.77(10) . . ?
O2 C7 C9 113.39(11) . . ?
O2 C7 C6 108.89(10) . . ?
C9 C7 C8 110.08(10) . . ?
C6 C7 C8 101.48(11) . . ?
C6 C7 C9 113.51(11) . . ?
C12 C9 C7 127.07(12) . . ?
C12 C9 C10 106.20(12) . . ?
C10 C9 C7 126.73(12) . . ?
C1 C6 C7 109.05(12) . . ?
C5 C6 C7 131.23(16) . . ?
C5 C6 C1 119.72(15) . . ?
C6 C1 N1 109.64(12) . . ?
C2 C1 N1 127.55(17) . . ?
C2 C1 C6 122.81(16) . . ?
C15 C14 C19 118.63(14) . . ?
C15 C14 C13 121.71(13) . . ?
C19 C14 C13 119.48(13) . . ?
N2 C12 C9 108.59(12) . . ?
N2 C12 H12 125.7 . . ?
C9 C12 H12 125.7 . . ?
C9 C10 H10 126.2 . . ?
C11 C10 C9 107.57(13) . . ?
C11 C10 H10 126.2 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.52(14) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.13(15) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.84(15) . . ?
C18 C17 H17 120.1 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.69(15) . . ?
C18 C19 H19 119.7 . . ?
N1 C13 C14 113.41(12) . . ?
N1 C13 H13A 108.9 . . ?
N1 C13 H13B 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
N2 C11 C10 108.28(13) . . ?
N2 C11 H11 125.9 . . ?
C10 C11 H11 125.9 . . ?
C17 C18 C19 120.18(14) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C6 C5 H5 121.1 . . ?
C6 C5 C4 117.8(2) . . ?
C4 C5 H5 121.1 . . ?
C1 C2 H2B 121.4 . . ?
C3 C2 C1 117.2(2) . . ?
C3 C2 H2B 121.4 . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.31(18) . . ?
C3 C4 H4 119.3 . . ?
C2 C3 C4 121.16(17) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1_$1 0.82 1.92 2.7325(13) 170.4 3_766


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.444
_oxdiff_exptl_absorpt_empirical_full_min 0.781
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate and Hexane'
