# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_KJ_5KN_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1854216'
_audit_update_record             
;
2018-07-06 deposited with the CCDC.
2018-11-07 downloaded from the CCDC.
;
_audit_creation_date             2018-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N O2'
_chemical_formula_sum            'C12 H11 N O2'
_chemical_formula_weight         201.22
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.4403(5)
_cell_length_b                   7.5372(5)
_cell_length_c                   10.8823(7)
_cell_angle_alpha                100.819(2)
_cell_angle_beta                 96.705(2)
_cell_angle_gamma                113.4590(10)
_cell_volume                     537.32(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5539
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      3.05
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.6
_exptl_absorpt_correction_T_min  0.6
_exptl_absorpt_correction_type   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2437
_exptl_crystal_description       plate
_exptl_crystal_F_000             212.1092
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16679
_diffrn_reflns_theta_full        28.3523
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         3.05
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.9959
_diffrn_measured_fraction_theta_max 0.9959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              9
_reflns_limit_k_min              -10
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1743
_reflns_number_total             2669
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR97 (Burla et al.,  2007)'
_refine_diff_density_max         0.4518
_refine_diff_density_min         -0.3159
_refine_diff_density_rms         0.0535
_refine_ls_d_res_high            0.7483
_refine_ls_d_res_low             6.6819
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.1028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    19
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2669
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0635
_refine_ls_restrained_S_all      1.1028
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0750P)²+0.1873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1668
_refine_ls_wR_factor_ref         0.2003
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
O1 O 0.2030(3) 0.0938(2) 0.64942(17) 0.0790(6) Uani 1.000000 .
O2 O 0.3966(3) 0.3506(2) 0.81646(16) 0.0735(5) Uani 1.000000 .
N1 N 0.5341(4) 0.7888(3) 0.7517(2) 0.0890(8) Uani 1.000000 .
C1 C 0.0698(4) 0.3790(4) 0.2962(2) 0.0674(6) Uani 1.000000 .
H1 H 0.0080(4) 0.2399(4) 0.2758(2) 0.0809(8) Uiso 1.000000 R
C2 C 0.0472(5) 0.4765(5) 0.2046(2) 0.0823(8) Uani 1.000000 .
H2 H -0.0292(5) 0.4034(5) 0.1230(2) 0.0988(10) Uiso 1.000000 R
C3 C 0.1374(4) 0.6812(5) 0.2338(3) 0.0777(8) Uani 1.000000 .
H3 H 0.1257(4) 0.7469(5) 0.1712(3) 0.0932(9) Uiso 1.000000 R
C4 C 0.2440(4) 0.7888(4) 0.3542(3) 0.0779(8) Uani 1.000000 .
H4 H 0.3014(4) 0.9278(4) 0.3743(3) 0.0935(9) Uiso 1.000000 R
C5 C 0.2675(3) 0.6925(3) 0.4465(2) 0.0663(6) Uani 1.000000 .
H5 H 0.3405(3) 0.7674(3) 0.5286(2) 0.0796(7) Uiso 1.000000 R
C6 C 0.1831(3) 0.4849(3) 0.41835(19) 0.0498(5) Uani 1.000000 .
C7 C 0.2002(3) 0.3688(3) 0.5079(2) 0.0504(5) Uani 1.000000 .
H7 H 0.1248(3) 0.2313(3) 0.4762(2) 0.0604(6) Uiso 1.000000 R
C8 C 0.3054(3) 0.4253(3) 0.6276(2) 0.0492(5) Uani 1.000000 .
C9 C 0.4314(3) 0.6279(3) 0.6964(2) 0.0585(6) Uani 1.000000 .
C10 C 0.2940(3) 0.2696(3) 0.6967(2) 0.0569(5) Uani 1.000000 .
C11 C 0.4066(5) 0.2130(4) 0.8935(3) 0.0835(8) Uani 1.000000 .
H11a H 0.4088(5) 0.0959(4) 0.8398(3) 0.1002(10) Uiso 1.000000 R
H11b H 0.5279(5) 0.2786(4) 0.9601(3) 0.1002(10) Uiso 1.000000 R
C12 C 0.2322(5) 0.1543(5) 0.9502(3) 0.0977(10) Uani 1.000000 .
H12a H 0.2306(19) 0.2711(6) 1.0026(18) 0.1466(15) Uiso 1.000000 GR
H12b H 0.1130(5) 0.087(3) 0.8837(3) 0.1466(15) Uiso 1.000000 GR
H12c H 0.2372(18) 0.066(3) 1.0020(18) 0.1466(15) Uiso 1.000000 GR


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 C10 1.195(2) . ?
O2 C10 1.324(3) . ?
O2 C11 1.469(3) . ?
N1 C9 1.139(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.378(4) . ?
C1 C6 1.385(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.359(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(3) . ?
C6 C7 1.453(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.334(3) . ?
C8 C9 1.428(3) . ?
C8 C10 1.489(3) . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?
C11 C12 1.447(4) . ?
C12 H12a 0.9600 . ?
C12 H12b 0.9600 . ?
C12 H12c 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
C11 O2 C10 117.07(18) . . ?
C2 C1 H1 119.50(16) . . ?
C6 C1 H1 119.50(13) . . ?
C6 C1 C2 121.0(2) . . ?
H2 C2 C1 120.04(16) . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.04(16) . . ?
H3 C3 C2 119.90(16) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.90(15) . . ?
H4 C4 C3 119.86(15) . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.86(16) . . ?
H5 C5 C4 119.64(16) . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.64(13) . . ?
C5 C6 C1 117.8(2) . . ?
C7 C6 C1 116.98(19) . . ?
C7 C6 C5 125.19(19) . . ?
H7 C7 C6 114.43(11) . . ?
C8 C7 C6 131.14(18) . . ?
C8 C7 H7 114.43(11) . . ?
C9 C8 C7 124.54(18) . . ?
C10 C8 C7 119.07(17) . . ?
C10 C8 C9 116.39(18) . . ?
C8 C9 N1 179.0(3) . . ?
O2 C10 O1 124.6(2) . . ?
C8 C10 O1 123.9(2) . . ?
C8 C10 O2 111.52(17) . . ?
H11a C11 O2 110.03(14) . . ?
H11b C11 O2 110.03(13) . . ?
H11b C11 H11a 108.4 . . ?
C12 C11 O2 108.3(3) . . ?
C12 C11 H11a 110.03(18) . . ?
C12 C11 H11b 110.03(17) . . ?
H12a C12 C11 109.5 . . ?
H12b C12 C11 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C11 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
