# Electronic Supplementary Material (ESI) for ChemComm.
# 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_BA-03-105-C
_database_code_depnum_ccdc_archive 'CCDC 2083663'
loop_
_audit_author_name
_audit_author_address
'Shohei Katao'
;Nara Institute of Science and Technology (NAIST)
Japan
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C11 H9 N O3'
_chemical_formula_moiety         'C11 H9 N O3'
_chemical_formula_weight         203.20
_chemical_melting_point          433

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.7867(4)
_cell_length_b                   3.95279(13)
_cell_length_c                   21.3580(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.388(6)
_cell_angle_gamma                90.0000
_cell_volume                     910.63(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11636
_cell_measurement_theta_min      2.11
_cell_measurement_theta_max      27.48
_cell_measurement_temperature    103
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424.00
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.687
_exptl_absorpt_correction_T_max  0.992

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      103
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            14163
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.418
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2081
_reflns_number_gt                1880
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1180
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2081
_refine_ls_number_parameters     137
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0753P)²+0.2412P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.66
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.58179(8) 1.0308(2) 0.43350(4) 0.0200(2) Uani 1 1 d . . . . .
O2 O 0.13200(8) 0.2017(2) 0.43894(4) 0.0245(2) Uani 1 1 d . . . . .
O3 O 0.22903(8) 0.4902(2) 0.51608(4) 0.0205(2) Uani 1 1 d . . . . .
N1 N 0.40537(9) 0.7192(2) 0.44210(4) 0.0161(2) Uani 1 1 d . . . . .
H1 H 0.402133 0.761892 0.482497 0.019 Uiso 1 1 calc R U . . .
C1 C 0.50264(10) 0.8478(3) 0.40873(5) 0.0158(2) Uani 1 1 d . . . . .
C2 C 0.31212(10) 0.5259(3) 0.41558(5) 0.0160(3) Uani 1 1 d . . . . .
C3 C 0.31002(10) 0.4523(3) 0.35387(5) 0.0169(3) Uani 1 1 d . . . . .
H3 H 0.243949 0.322844 0.336587 0.020 Uiso 1 1 calc R U . . .
C4 C 0.40825(10) 0.5708(3) 0.31450(5) 0.0160(3) Uani 1 1 d . . . . .
C5 C 0.41146(11) 0.5030(3) 0.24967(5) 0.0187(3) Uani 1 1 d . . . . .
H5 H 0.346646 0.375703 0.230691 0.022 Uiso 1 1 calc R U . . .
C6 C 0.50816(11) 0.6205(3) 0.21362(5) 0.0200(3) Uani 1 1 d . . . . .
H6 H 0.508958 0.576526 0.169892 0.024 Uiso 1 1 calc R U . . .
C7 C 0.60511(11) 0.8043(3) 0.24136(5) 0.0197(3) Uani 1 1 d . . . . .
H7 H 0.671960 0.881937 0.216449 0.024 Uiso 1 1 calc R U . . .
C8 C 0.60387(10) 0.8730(3) 0.30488(5) 0.0183(3) Uani 1 1 d . . . . .
H8 H 0.669842 0.997298 0.323527 0.022 Uiso 1 1 calc R U . . .
C9 C 0.50530(10) 0.7594(3) 0.34162(5) 0.0159(3) Uani 1 1 d . . . . .
C10 C 0.21324(10) 0.3879(3) 0.45718(5) 0.0174(3) Uani 1 1 d . . . . .
C11 C 0.14568(12) 0.3449(3) 0.56155(5) 0.0240(3) Uani 1 1 d . . . . .
H11A H 0.145760 0.098018 0.557377 0.029 Uiso 1 1 calc R U . . .
H11B H 0.061638 0.431155 0.554237 0.029 Uiso 1 1 calc R U . . .
H11C H 0.173173 0.407164 0.603830 0.029 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C1 1.2352(14) . ?
O2 C10 1.2070(15) . ?
O3 C10 1.3313(14) . ?
O3 C11 1.4468(14) . ?
N1 C1 1.3702(15) . ?
N1 C2 1.3815(14) . ?
N1 H1 0.8800 . ?
C1 C9 1.4758(14) . ?
C2 C3 1.3499(15) . ?
C2 C10 1.4958(16) . ?
C3 C4 1.4357(16) . ?
C3 H3 0.9500 . ?
C4 C9 1.4065(16) . ?
C4 C5 1.4110(15) . ?
C5 C6 1.3810(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.4015(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3838(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.3999(16) . ?
C8 H8 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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
C10 O3 C11 115.95(9) . . ?
C1 N1 C2 123.36(9) . . ?
C1 N1 H1 118.3 . . ?
C2 N1 H1 118.3 . . ?
O1 C1 N1 121.60(10) . . ?
O1 C1 C9 122.46(10) . . ?
N1 C1 C9 115.93(10) . . ?
C3 C2 N1 121.80(11) . . ?
C3 C2 C10 119.60(10) . . ?
N1 C2 C10 118.58(10) . . ?
C2 C3 C4 119.60(11) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C9 C4 C5 118.80(10) . . ?
C9 C4 C3 118.81(10) . . ?
C5 C4 C3 122.40(10) . . ?
C6 C5 C4 120.46(11) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.18(10) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.28(11) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 119.93(11) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C4 120.34(10) . . ?
C8 C9 C1 119.23(10) . . ?
C4 C9 C1 120.41(10) . . ?
O2 C10 O3 125.32(11) . . ?
O2 C10 C2 123.36(10) . . ?
O3 C10 C2 111.30(10) . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
C2 N1 C1 O1 177.10(10) . . . . ?
C2 N1 C1 C9 -1.81(16) . . . . ?
C1 N1 C2 C3 -0.62(17) . . . . ?
C1 N1 C2 C10 177.63(10) . . . . ?
N1 C2 C3 C4 1.31(17) . . . . ?
C10 C2 C3 C4 -176.92(9) . . . . ?
C2 C3 C4 C9 0.56(17) . . . . ?
C2 C3 C4 C5 -179.91(10) . . . . ?
C9 C4 C5 C6 -0.10(17) . . . . ?
C3 C4 C5 C6 -179.63(10) . . . . ?
C4 C5 C6 C7 0.94(18) . . . . ?
C5 C6 C7 C8 -0.82(18) . . . . ?
C6 C7 C8 C9 -0.13(18) . . . . ?
C7 C8 C9 C4 0.97(17) . . . . ?
C7 C8 C9 C1 -177.32(10) . . . . ?
C5 C4 C9 C8 -0.85(17) . . . . ?
C3 C4 C9 C8 178.70(10) . . . . ?
C5 C4 C9 C1 177.42(10) . . . . ?
C3 C4 C9 C1 -3.04(16) . . . . ?
O1 C1 C9 C8 3.00(17) . . . . ?
N1 C1 C9 C8 -178.10(9) . . . . ?
O1 C1 C9 C4 -175.29(10) . . . . ?
N1 C1 C9 C4 3.61(16) . . . . ?
C11 O3 C10 O2 4.27(17) . . . . ?
C11 O3 C10 C2 -174.16(9) . . . . ?
C3 C2 C10 O2 2.47(18) . . . . ?
N1 C2 C10 O2 -175.83(11) . . . . ?
C3 C2 C10 O3 -179.07(10) . . . . ?
N1 C2 C10 O3 2.64(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 . . 3_676 2.8373(12) 0.880 1.979 164.7 no
N1 H1 O3 . . . 2.6410(13) 0.880 2.274 104.9 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
'Methyl 1-oxo-1,2-dihydroisoquinoline-3-carboxylate'
