# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_np_no2
_audit_block_doi                 10.5517/ccdc.csd.cc204bs9
_database_code_depnum_ccdc_archive 'CCDC 1851220'
_audit_update_record             
;
2018-09-26 deposited with the CCDC.
2018-09-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H13 N O3'
_chemical_formula_sum            'C20 H13 N O3'
_chemical_formula_weight         315.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.2086(2)
_cell_length_b                   12.6711(4)
_cell_length_c                   8.3699(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.408(3)
_cell_angle_gamma                90
_cell_volume                     756.30(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5021
_cell_measurement_theta_min      6.1990
_cell_measurement_theta_max      79.1610

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_exptl_absorpt_coefficient_mu    0.765
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.36024
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6678
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.342
_diffrn_reflns_theta_max         79.882
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.814
_diffrn_reflns_point_group_measured_fraction_full 0.861
_reflns_number_total             2685
_reflns_number_gt                2509
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.593
_reflns_Friedel_fraction_max     0.635
_reflns_Friedel_fraction_full    0.708

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0771P)²+0.0207P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 875 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.33(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2685
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.1169
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.1321(2) 0.67919(12) 0.4664(2) 0.0452(4) Uani 1 1 d . . . . .
N22 N -0.1449(3) 0.3526(2) 0.0550(3) 0.0579(6) Uani 1 1 d . . . . .
O24 O -0.1909(4) 0.3717(2) -0.0878(3) 0.0765(7) Uani 1 1 d . . . . .
O23 O -0.1469(5) 0.2641(2) 0.1112(4) 0.0863(8) Uani 1 1 d . . . . .
C15 C 0.0635(3) 0.59692(19) 0.3659(3) 0.0404(5) Uani 1 1 d . . . . .
C11 C -0.0318(3) 0.4172(2) 0.3267(3) 0.0442(5) Uani 1 1 d . . . . .
H11 H -0.0512 0.3500 0.3659 0.053 Uiso 1 1 calc R U . . .
C9 C 0.1080(3) 0.4735(2) 0.6024(3) 0.0422(5) Uani 1 1 d . . . . .
H9 H 0.0351 0.4272 0.6531 0.051 Uiso 1 1 calc R U . . .
C12 C -0.0782(3) 0.4393(2) 0.1644(3) 0.0456(6) Uani 1 1 d . . . . .
C16 C 0.3199(3) 0.4771(2) 0.8609(3) 0.0436(5) Uani 1 1 d . . . . .
C10 C 0.0446(3) 0.49679(19) 0.4316(3) 0.0406(5) Uani 1 1 d . . . . .
C2 C 0.3252(3) 0.66669(19) 0.5153(3) 0.0407(5) Uani 1 1 d . . . . .
C8 C 0.2633(3) 0.51340(18) 0.6927(3) 0.0411(5) Uani 1 1 d . . . . .
C14 C 0.0124(4) 0.6181(2) 0.2037(3) 0.0472(6) Uani 1 1 d . . . . .
H14 H 0.0263 0.6858 0.1644 0.057 Uiso 1 1 calc R U . . .
C13 C -0.0594(4) 0.5384(2) 0.0996(3) 0.0497(6) Uani 1 1 d . . . . .
H13 H -0.0939 0.5511 -0.0102 0.060 Uiso 1 1 calc R U . . .
C17 C 0.3963(4) 0.5480(3) 0.9804(3) 0.0497(6) Uani 1 1 d . . . . .
H17 H 0.4130 0.6183 0.9538 0.060 Uiso 1 1 calc R U . . .
C7 C 0.3903(3) 0.58801(19) 0.6259(3) 0.0397(5) Uani 1 1 d . . . . .
C18 C 0.4477(4) 0.5144(3) 1.1390(4) 0.0632(8) Uani 1 1 d . . . . .
H18 H 0.4975 0.5624 1.2178 0.076 Uiso 1 1 calc R U . . .
C3 C 0.4447(4) 0.7355(2) 0.4521(3) 0.0528(6) Uani 1 1 d . . . . .
H3 H 0.3970 0.7873 0.3787 0.063 Uiso 1 1 calc R U . . .
C5 C 0.7060(4) 0.6486(3) 0.6077(4) 0.0547(7) Uani 1 1 d . . . . .
H5 H 0.8347 0.6423 0.6393 0.066 Uiso 1 1 calc R U . . .
C6 C 0.5854(4) 0.5805(2) 0.6689(3) 0.0476(6) Uani 1 1 d . . . . .
H6 H 0.6345 0.5280 0.7406 0.057 Uiso 1 1 calc R U . . .
C4 C 0.6371(4) 0.7261(3) 0.5000(4) 0.0584(7) Uani 1 1 d . . . . .
H4 H 0.7190 0.7721 0.4592 0.070 Uiso 1 1 calc R U . . .
C21 C 0.2993(4) 0.3719(3) 0.9049(4) 0.0544(6) Uani 1 1 d . . . . .
H21 H 0.2508 0.3231 0.8268 0.065 Uiso 1 1 calc R U . . .
C20 C 0.3499(5) 0.3392(3) 1.0625(5) 0.0685(9) Uani 1 1 d . . . . .
H20 H 0.3335 0.2691 1.0904 0.082 Uiso 1 1 calc R U . . .
C19 C 0.4253(5) 0.4110(4) 1.1794(4) 0.0712(10) Uani 1 1 d . . . . .
H19 H 0.4607 0.3888 1.2853 0.085 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.385(3) . ?
O1 C2 1.401(3) . ?
N22 O23 1.216(4) . ?
N22 O24 1.217(4) . ?
N22 C12 1.466(3) . ?
C15 C14 1.380(3) . ?
C15 C10 1.398(3) . ?
C11 C12 1.379(4) . ?
C11 C10 1.396(3) . ?
C11 H11 0.9300 . ?
C9 C8 1.354(3) . ?
C9 C10 1.465(3) . ?
C9 H9 0.9300 . ?
C12 C13 1.383(4) . ?
C16 C17 1.397(4) . ?
C16 C21 1.397(4) . ?
C16 C8 1.480(4) . ?
C2 C3 1.383(4) . ?
C2 C7 1.395(3) . ?
C8 C7 1.481(3) . ?
C14 C13 1.383(4) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C17 C18 1.392(4) . ?
C17 H17 0.9300 . ?
C7 C6 1.403(3) . ?
C18 C19 1.369(6) . ?
C18 H18 0.9300 . ?
C3 C4 1.392(4) . ?
C3 H3 0.9300 . ?
C5 C4 1.375(5) . ?
C5 C6 1.376(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C4 H4 0.9300 . ?
C21 C20 1.380(4) . ?
C21 H21 0.9300 . ?
C20 C19 1.387(6) . ?
C20 H20 0.9300 . ?
C19 H19 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
C15 O1 C2 110.11(17) . . ?
O23 N22 O24 123.1(3) . . ?
O23 N22 C12 118.1(3) . . ?
O24 N22 C12 118.8(3) . . ?
C14 C15 O1 118.1(2) . . ?
C14 C15 C10 122.4(2) . . ?
O1 C15 C10 119.4(2) . . ?
C12 C11 C10 119.3(2) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C8 C9 C10 125.7(2) . . ?
C8 C9 H9 117.2 . . ?
C10 C9 H9 117.2 . . ?
C11 C12 C13 123.2(2) . . ?
C11 C12 N22 118.3(3) . . ?
C13 C12 N22 118.5(2) . . ?
C17 C16 C21 118.1(3) . . ?
C17 C16 C8 120.4(2) . . ?
C21 C16 C8 121.5(3) . . ?
C11 C10 C15 117.4(2) . . ?
C11 C10 C9 120.4(2) . . ?
C15 C10 C9 122.2(2) . . ?
C3 C2 C7 122.4(2) . . ?
C3 C2 O1 117.7(2) . . ?
C7 C2 O1 119.9(2) . . ?
C9 C8 C16 120.3(2) . . ?
C9 C8 C7 122.3(2) . . ?
C16 C8 C7 117.2(2) . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C13 C12 117.7(2) . . ?
C14 C13 H13 121.2 . . ?
C12 C13 H13 121.2 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C2 C7 C6 116.5(2) . . ?
C2 C7 C8 122.7(2) . . ?
C6 C7 C8 120.8(2) . . ?
C19 C18 C17 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C2 C3 C4 119.1(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 121.7(3) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C20 C21 C16 121.0(3) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C18 C19 C20 120.1(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.049

