# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_exp_565_ak-sj-280
_database_code_depnum_ccdc_archive 'CCDC 1978834'
loop_
_audit_author_name
_audit_author_address
'Krishnan Rangan'
;BITS Pilani Hyderabad Campus
India
;
_audit_update_record             
;
2020-01-20 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;
_audit_creation_date             2020-01-20
_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         'C20 H14 N2 O'
_chemical_formula_sum            'C20 H14 N2 O'
_chemical_formula_weight         298.33
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.3127(2)
_cell_length_b                   17.1849(3)
_cell_length_c                   20.9916(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2998.71(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7547
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      79.1790
_cell_measurement_theta_min      5.1860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78377
_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            Yellow
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10545
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.542
_diffrn_reflns_theta_min         4.212
_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 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     43.00  69.00   0.50    2.72    --    0.00  37.00 150.00   52
  2  ω    -45.00  14.00   0.50    2.72    --    0.00 -37.00-120.00  118
  3  ω    -22.00  65.00   0.50    2.72    --    0.00  57.00  60.00  174
  4  ω    147.00 185.00   0.50   10.92    --  107.20  30.00 -60.00   76
  5  ω     59.00 123.00   0.50   10.92    --  107.20 -61.00-180.00  128
  6  ω     92.00 194.00   0.50   10.92    --  107.20  45.00-150.00  204
  7  ω     19.00  92.00   0.50   10.92    --  107.20 -61.00 -90.00  146
  8  ω     33.00 133.00   0.50   10.92    --  107.20 -15.00  30.00  200
;
_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      -0.0249451000
_diffrn_orient_matrix_UB_12      -0.0257324000
_diffrn_orient_matrix_UB_13      0.0695490000
_diffrn_orient_matrix_UB_21      -0.1524062000
_diffrn_orient_matrix_UB_22      0.0506045000
_diffrn_orient_matrix_UB_23      0.0039014000
_diffrn_orient_matrix_UB_31      -0.1024595000
_diffrn_orient_matrix_UB_32      -0.0693689000
_diffrn_orient_matrix_UB_33      -0.0231182000
_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                2968
_reflns_number_total             3204
_reflns_odcompleteness_completeness 99.85
_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         0.239
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.096
_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)+(0.0647P)²+1.2434P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1239
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C16(H16), C4(H4), C2(H2), C3(H3), C17(H17), C9(H9), C13(H13),
 C12(H12), C20(H20), C18(H18), C11(H11), C19(H19), C10(H10)
;
_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
O1 O 0.29754(11) 0.46900(6) 0.30521(4) 0.0250(2) Uani 1 1 d . . . . .
N1 N 0.44399(13) 0.42753(6) 0.42115(5) 0.0180(2) Uani 1 1 d . . . . .
N2 N 0.63864(13) 0.36024(6) 0.47169(5) 0.0201(2) Uani 1 1 d . . . . .
C8 C 0.83725(15) 0.34603(7) 0.38461(6) 0.0188(3) Uani 1 1 d . . . . .
C5 C 0.29999(15) 0.46868(7) 0.41739(6) 0.0184(3) Uani 1 1 d . . . . .
C7 C 0.68244(15) 0.37375(7) 0.40979(6) 0.0185(3) Uani 1 1 d . . . . .
C1 C 0.49536(15) 0.39334(7) 0.47825(6) 0.0188(3) Uani 1 1 d . . . . .
C6 C 0.56486(15) 0.41440(7) 0.37760(6) 0.0193(3) Uani 1 1 d . . . . .
H6 H 0.566769 0.429802 0.335134 0.023 Uiso 1 1 calc R . . . .
C15 C 0.11744(15) 0.55865(7) 0.35194(6) 0.0191(3) Uani 1 1 d . . . . .
C14 C 0.24411(15) 0.49686(7) 0.35461(6) 0.0191(3) Uani 1 1 d . . . . .
C16 C 0.11980(15) 0.62370(7) 0.39207(6) 0.0205(3) Uani 1 1 d . . . . .
H16 H 0.197270 0.627867 0.423849 0.025 Uiso 1 1 calc R . . . .
C4 C 0.20970(15) 0.47497(7) 0.47167(6) 0.0206(3) Uani 1 1 d . . . . .
H4 H 0.114086 0.503015 0.470254 0.025 Uiso 1 1 calc R . . . .
C2 C 0.39742(16) 0.39948(7) 0.53282(6) 0.0219(3) Uani 1 1 d . . . . .
H2 H 0.428392 0.375831 0.570736 0.026 Uiso 1 1 calc R . . . .
C3 C 0.25669(16) 0.44037(7) 0.52969(6) 0.0221(3) Uani 1 1 d . . . . .
H3 H 0.192168 0.445362 0.565649 0.027 Uiso 1 1 calc R . . . .
C17 C 0.00567(16) 0.68204(7) 0.38414(6) 0.0229(3) Uani 1 1 d . . . . .
H17 H 0.008080 0.725770 0.410218 0.027 Uiso 1 1 calc R . . . .
C9 C 0.87395(15) 0.35202(7) 0.31976(6) 0.0219(3) Uani 1 1 d . . . . .
H9 H 0.801701 0.376032 0.292240 0.026 Uiso 1 1 calc R . . . .
C13 C 0.94954(16) 0.31118(7) 0.42518(6) 0.0232(3) Uani 1 1 d . . . . .
H13 H 0.927177 0.306845 0.468439 0.028 Uiso 1 1 calc R . . . .
C12 C 1.09415(17) 0.28300(8) 0.40143(7) 0.0266(3) Uani 1 1 d . . . . .
H12 H 1.168644 0.260672 0.428967 0.032 Uiso 1 1 calc R . . . .
C20 C 0.00067(17) 0.55276(8) 0.30456(6) 0.0239(3) Uani 1 1 d . . . . .
H20 H 0.000324 0.510081 0.277325 0.029 Uiso 1 1 calc R . . . .
C18 C -0.11177(17) 0.67534(8) 0.33751(7) 0.0257(3) Uani 1 1 d . . . . .
H18 H -0.188432 0.714315 0.332714 0.031 Uiso 1 1 calc R . . . .
C11 C 1.12804(16) 0.28796(8) 0.33700(7) 0.0274(3) Uani 1 1 d . . . . .
H11 H 1.224283 0.268383 0.321092 0.033 Uiso 1 1 calc R . . . .
C19 C -0.11515(17) 0.61036(8) 0.29788(7) 0.0273(3) Uani 1 1 d . . . . .
H19 H -0.194793 0.605586 0.267011 0.033 Uiso 1 1 calc R . . . .
C10 C 1.01710(17) 0.32244(8) 0.29625(7) 0.0266(3) Uani 1 1 d . . . . .
H10 H 1.039185 0.325662 0.252902 0.032 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
O1 C14 1.2257(15) . ?
N1 C5 1.3925(15) . ?
N1 C1 1.4016(15) . ?
N1 C6 1.3770(16) . ?
N2 C7 1.3693(16) . ?
N2 C1 1.3271(16) . ?
C8 C7 1.4705(17) . ?
C8 C9 1.3988(18) . ?
C8 C13 1.3982(18) . ?
C5 C14 1.4788(17) . ?
C5 C4 1.3688(17) . ?
C7 C6 1.3784(18) . ?
C1 C2 1.4093(18) . ?
C6 H6 0.9300 . ?
C15 C14 1.4964(17) . ?
C15 C16 1.3999(17) . ?
C15 C20 1.3933(18) . ?
C16 H16 0.9300 . ?
C16 C17 1.3903(18) . ?
C4 H4 0.9300 . ?
C4 C3 1.4104(18) . ?
C2 H2 0.9300 . ?
C2 C3 1.3662(19) . ?
C3 H3 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.387(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.3849(19) . ?
C13 H13 0.9300 . ?
C13 C12 1.3885(19) . ?
C12 H12 0.9300 . ?
C12 C11 1.384(2) . ?
C20 H20 0.9300 . ?
C20 C19 1.3879(19) . ?
C18 H18 0.9300 . ?
C18 C19 1.3928(19) . ?
C11 H11 0.9300 . ?
C11 C10 1.390(2) . ?
C19 H19 0.9300 . ?
C10 H10 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
C5 N1 C1 121.55(10) . . ?
C6 N1 C5 132.29(11) . . ?
C6 N1 C1 106.07(10) . . ?
C1 N2 C7 105.34(10) . . ?
C9 C8 C7 121.12(11) . . ?
C13 C8 C7 120.27(11) . . ?
C13 C8 C9 118.59(12) . . ?
N1 C5 C14 119.13(11) . . ?
C4 C5 N1 117.66(11) . . ?
C4 C5 C14 122.94(11) . . ?
N2 C7 C8 121.26(11) . . ?
N2 C7 C6 111.26(11) . . ?
C6 C7 C8 127.48(12) . . ?
N1 C1 C2 119.20(11) . . ?
N2 C1 N1 111.37(11) . . ?
N2 C1 C2 129.41(12) . . ?
N1 C6 C7 105.96(11) . . ?
N1 C6 H6 127.0 . . ?
C7 C6 H6 127.0 . . ?
C16 C15 C14 122.29(11) . . ?
C20 C15 C14 117.74(11) . . ?
C20 C15 C16 119.81(12) . . ?
O1 C14 C5 120.81(11) . . ?
O1 C14 C15 120.03(11) . . ?
C5 C14 C15 119.14(10) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.62(12) . . ?
C17 C16 H16 120.2 . . ?
C5 C4 H4 118.9 . . ?
C5 C4 C3 122.25(12) . . ?
C3 C4 H4 118.9 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.60(12) . . ?
C3 C2 H2 120.2 . . ?
C4 C3 H3 120.1 . . ?
C2 C3 C4 119.71(12) . . ?
C2 C3 H3 120.1 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.32(12) . . ?
C18 C17 H17 119.8 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.48(12) . . ?
C10 C9 H9 119.8 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.58(12) . . ?
C12 C13 H13 119.7 . . ?
C13 C12 H12 119.8 . . ?
C11 C12 C13 120.36(13) . . ?
C11 C12 H12 119.8 . . ?
C15 C20 H20 119.9 . . ?
C19 C20 C15 120.24(12) . . ?
C19 C20 H20 119.9 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.15(12) . . ?
C19 C18 H18 119.9 . . ?
C12 C11 H11 120.2 . . ?
C12 C11 C10 119.50(12) . . ?
C10 C11 H11 120.2 . . ?
C20 C19 C18 119.83(13) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C9 C10 C11 120.47(13) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?


_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 1.373
_oxdiff_exptl_absorpt_empirical_full_min 0.774
