# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_CNAntr_0maa_aa_a
_database_code_depnum_ccdc_archive 'CCDC 2096046'
loop_
_audit_author_name
_audit_author_address
Owatari
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2021-07-13 deposited with the CCDC.	2022-04-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 N O2'
_chemical_formula_weight         249.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'

_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, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   14.732(9)
_cell_length_b                   10.702(7)
_cell_length_c                   7.661(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1208.0(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2078
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.02

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2078
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.352
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_full        25.020
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.934
_reflns_number_total             1037
_reflns_number_gt                984
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_max     0.884
_reflns_Friedel_fraction_full    0.884

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)²+0.4619P] 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-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.020(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 406 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1037
_refine_ls_number_parameters     98
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1485
_refine_ls_wR_factor_gt          0.1456
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.138
_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
O001 O 0.500000 0.1558(3) 0.8092(5) 0.0364(9) Uani 1 2 d S T P . .
O002 O 0.500000 0.5813(3) 0.4400(6) 0.0674(15) Uani 1 2 d S T P . .
C1 C 0.500000 0.2185(4) 0.6463(5) 0.0254(10) Uani 1 2 d S T P . .
C004 C 0.5861(2) 0.2932(3) 0.6199(4) 0.0289(8) Uani 1 1 d . . . . .
N005 N 0.500000 0.1862(5) 0.1915(7) 0.0517(13) Uani 1 2 d S T P . .
C006 C 0.500000 0.1511(3) 0.3326(6) 0.0310(11) Uani 1 2 d S T P . .
C007 C 0.5860(2) 0.4112(3) 0.5436(4) 0.0361(9) Uani 1 1 d . . . . .
C008 C 0.500000 0.1083(4) 0.5130(6) 0.0298(10) Uani 1 2 d S T P . .
H00A H 0.553210 0.056861 0.532741 0.036 Uiso 0.5 1 calc R U P . .
H00B H 0.446790 0.056861 0.532741 0.036 Uiso 0.5 1 calc R U P . .
C009 C 0.500000 0.4757(4) 0.5008(6) 0.0396(13) Uani 1 2 d S T P . .
C00A C 0.6682(2) 0.2385(4) 0.6671(5) 0.0458(11) Uani 1 1 d . . . . .
H00C H 0.668919 0.160131 0.719506 0.055 Uiso 1 1 calc R U . . .
C00B C 0.6687(4) 0.4720(4) 0.5130(6) 0.0639(15) Uani 1 1 d . . . . .
H00D H 0.669011 0.551010 0.462498 0.077 Uiso 1 1 calc R U . . .
C00C C 0.7499(3) 0.3019(6) 0.6353(7) 0.0743(18) Uani 1 1 d . . . . .
H00E H 0.804842 0.265920 0.667777 0.089 Uiso 1 1 calc R U . . .
C00D C 0.7488(3) 0.4162(6) 0.5568(8) 0.083(2) Uani 1 1 d . . . . .
H00F H 0.803238 0.456563 0.532755 0.100 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
O001 C1 1.417(5) . ?
O002 C009 1.223(6) . ?
C1 C004 1.513(4) 4_655 ?
C1 C004 1.513(4) . ?
C1 C008 1.560(5) . ?
C004 C007 1.392(5) . ?
C004 C00A 1.391(5) . ?
N005 C006 1.144(7) . ?
C006 C008 1.456(6) . ?
C007 C00B 1.401(5) . ?
C007 C009 1.479(4) . ?
C008 H00A 0.9700 . ?
C008 H00B 0.9700 . ?
C00A C00C 1.403(6) . ?
C00A H00C 0.9300 . ?
C00B C00D 1.364(8) . ?
C00B H00D 0.9300 . ?
C00C C00D 1.363(9) . ?
C00C H00E 0.9300 . ?
C00D H00F 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
O001 C1 C004 111.6(2) . 4_655 ?
O001 C1 C004 111.6(2) . . ?
C004 C1 C004 114.0(4) 4_655 . ?
O001 C1 C008 102.7(3) . . ?
C004 C1 C008 108.2(2) 4_655 . ?
C004 C1 C008 108.2(2) . . ?
C007 C004 C00A 119.5(3) . . ?
C007 C004 C1 122.3(3) . . ?
C00A C004 C1 118.2(3) . . ?
N005 C006 C008 179.2(4) . . ?
C004 C007 C00B 119.4(4) . . ?
C004 C007 C009 121.2(3) . . ?
C00B C007 C009 119.4(4) . . ?
C006 C008 C1 112.6(3) . . ?
C006 C008 H00A 109.1 . . ?
C1 C008 H00A 109.1 . . ?
C006 C008 H00B 109.1 . . ?
C1 C008 H00B 109.1 . . ?
H00A C008 H00B 107.8 . . ?
O002 C009 C007 121.06(18) . . ?
O002 C009 C007 121.06(18) . 4_655 ?
C007 C009 C007 117.8(4) . 4_655 ?
C004 C00A C00C 119.8(4) . . ?
C004 C00A H00C 120.1 . . ?
C00C C00A H00C 120.1 . . ?
C00D C00B C007 120.5(4) . . ?
C00D C00B H00D 119.8 . . ?
C007 C00B H00D 119.8 . . ?
C00D C00C C00A 120.0(5) . . ?
C00D C00C H00E 120.0 . . ?
C00A C00C H00E 120.0 . . ?
C00C C00D C00B 120.8(4) . . ?
C00C C00D H00F 119.6 . . ?
C00B C00D H00F 119.6 . . ?

_refine_diff_density_max         0.261
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.055

