#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/13/4021395.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4021395
loop_
_publ_author_name
'Shin-ya Tanaka'
'Makoto Yasuda'
'Akio Baba'
_publ_contact_author_email       ' baba@chem.eng.osaka-u.ac.jp'
_publ_contact_author_fax         ' 81(6)68797387 '
_publ_contact_author_name        ' Dr Akio Baba'
_publ_contact_author_phone       ' 81(6)68797386 '
_publ_section_title
;
 Practical and Simple Synthesis of Substituted Quinolines
 by an HCl-DMSO System on a Large Scale:
 Remarkable Effect of the Chloride Ion
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              800
_journal_page_last               803
_journal_paper_doi               10.1021/jo052004y
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C22 H17 N '
_chemical_formula_sum            'C22 H17 N'
_chemical_formula_weight         295.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_date             'Tue Oct 19 19:04:15 2004'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                90
_cell_angle_beta                 94.71(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.878(3)
_cell_length_b                   5.461(3)
_cell_length_c                   21.321(2)
_cell_measurement_reflns_used    16
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      11.4
_cell_measurement_theta_min      10.3
_cell_volume                     1610.6(8)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_measured_fraction_theta_full 0.8229
_diffrn_measured_fraction_theta_max 0.8229
_diffrn_measurement_device_type  'Rigaku AFC5R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.102
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            2763
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_standards_decay_%        1.72
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.542
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     276
_refine_ls_number_reflns         2344
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          1.1461
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.05000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2393
_reflns_number_gt                763
_reflns_number_total             2344
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo052004ysi20050924_014141.cif
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C22 H17 N '
_cod_database_code               4021395
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,1/2-z
-x,-y,-z
1/2+x,1/2-y,1/2+z
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_calc_flag
N(1) N 0.1314(4) 0.160(1) 0.5017(3) 0.054(2) Uani 1.00 d
C(1) C 0.1862(5) 0.335(2) 0.5275(3) 0.049(2) Uani 1.00 d
C(2) C 0.1620(5) 0.415(2) 0.5921(3) 0.048(3) Uani 1.00 d
C(3) C 0.1091(7) 0.623(2) 0.5999(4) 0.080(4) Uani 1.00 d
C(4) C 0.0867(6) 0.692(2) 0.6603(4) 0.079(4) Uani 1.00 d
C(5) C 0.1196(6) 0.556(2) 0.7118(4) 0.069(3) Uani 1.00 d
C(6) C 0.1715(6) 0.350(2) 0.7039(4) 0.076(3) Uani 1.00 d
C(7) C 0.1928(6) 0.277(2) 0.6440(4) 0.066(3) Uani 1.00 d
C(8) C 0.2633(5) 0.446(2) 0.4977(3) 0.056(3) Uani 1.00 d
C(9) C 0.3255(6) 0.637(2) 0.5319(4) 0.066(3) Uani 1.00 d
C(10) C 0.3995(5) 0.536(2) 0.5808(4) 0.057(3) Uani 1.00 d
C(11) C 0.4181(6) 0.651(2) 0.6379(4) 0.074(3) Uani 1.00 d
C(12) C 0.4870(7) 0.558(2) 0.6826(4) 0.085(4) Uani 1.00 d
C(13) C 0.5368(7) 0.347(2) 0.6710(5) 0.082(4) Uani 1.00 d
C(14) C 0.5184(6) 0.230(2) 0.6145(5) 0.081(4) Uani 1.00 d
C(15) C 0.4503(6) 0.324(2) 0.5706(4) 0.070(4) Uani 1.00 d
C(16) C 0.2805(6) 0.365(2) 0.4396(4) 0.066(3) Uani 1.00 d
C(17) C 0.2247(5) 0.177(2) 0.4097(3) 0.058(3) Uani 1.00 d
C(18) C 0.2387(7) 0.080(2) 0.3508(4) 0.086(4) Uani 1.00 d
C(19) C 0.1840(7) -0.110(2) 0.3254(4) 0.083(4) Uani 1.00 d
C(20) C 0.1098(7) -0.211(2) 0.3589(5) 0.086(4) Uani 1.00 d
C(21) C 0.0942(6) -0.116(2) 0.4164(4) 0.069(3) Uani 1.00 d
C(22) C 0.1502(5) 0.074(2) 0.4435(3) 0.053(3) Uani 1.00 d
H(1) H 0.087(6) 0.72(2) 0.565(4) 0.11(1) Uiso 1.00 calc
H(2) H 0.040(8) 0.85(2) 0.668(5) 0.191(7) Uiso 1.00 calc
H(3) H 0.097(4) 0.60(1) 0.755(3) 0.08(1) Uiso 1.00 calc
H(4) H 0.191(6) 0.24(2) 0.744(4) 0.147(9) Uiso 1.00 calc
H(5) H 0.238(5) 0.15(1) 0.640(3) 0.07(1) Uiso 1.00 calc
H(6) H 0.284(5) 0.76(1) 0.556(3) 0.08(1) Uiso 1.00 calc
H(7) H 0.358(5) 0.73(1) 0.504(3) 0.08(1) Uiso 1.00 calc
H(8) H 0.385(5) 0.80(2) 0.648(3) 0.08(1) Uiso 1.00 calc
H(9) H 0.500(5) 0.63(1) 0.724(3) 0.08(1) Uiso 1.00 calc
H(10) H 0.583(5) 0.28(2) 0.703(4) 0.10(1) Uiso 1.00 calc
H(11) H 0.555(6) 0.08(2) 0.605(4) 0.105(10) Uiso 1.00 calc
H(12) H 0.444(3) 0.258(9) 0.529(2) 0.01(1) Uiso 1.00 calc
H(13) H 0.333(5) 0.45(1) 0.420(3) 0.08(1) Uiso 1.00 calc
H(14) H 0.287(5) 0.14(2) 0.327(3) 0.08(1) Uiso 1.00 calc
H(15) H 0.193(5) -0.18(2) 0.279(3) 0.10(1) Uiso 1.00 calc
H(16) H 0.072(5) -0.35(1) 0.341(3) 0.08(1) Uiso 1.00 calc
H(17) H 0.041(4) -0.16(1) 0.440(3) 0.07(1) Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(1) N(1) C(22) 118.7(6) yes
N(1) C(1) C(2) 115.4(6) yes
N(1) C(1) C(8) 123.6(7) yes
C(2) C(1) C(8) 121.0(7) yes
C(1) C(2) C(3) 120.8(7) yes
C(1) C(2) C(7) 119.8(8) yes
C(3) C(2) C(7) 119.4(7) yes
C(2) C(3) C(4) 119.7(8) yes
C(2) C(3) H(1) 120(5) no
C(4) C(3) H(1) 119(5) no
C(3) C(4) C(5) 120.4(9) yes
C(3) C(4) H(2) 122(5) no
C(5) C(4) H(2) 117(5) no
C(4) C(5) C(6) 119.7(9) yes
C(4) C(5) H(3) 119(3) no
C(6) C(5) H(3) 120(4) no
C(5) C(6) C(7) 120.5(9) yes
C(5) C(6) H(4) 117(5) no
C(7) C(6) H(4) 121(5) no
C(2) C(7) C(6) 120.3(8) yes
C(2) C(7) H(5) 119(4) no
C(6) C(7) H(5) 119(3) no
C(1) C(8) C(9) 120.1(7) yes
C(1) C(8) C(16) 117.6(8) yes
C(9) C(8) C(16) 122.2(8) yes
C(8) C(9) C(10) 114.3(8) yes
C(8) C(9) H(6) 111(4) no
C(8) C(9) H(7) 110(4) no
C(10) C(9) H(6) 105(3) no
C(10) C(9) H(7) 107(4) no
H(6) C(9) H(7) 107(6) no
C(9) C(10) C(11) 120.7(9) yes
C(9) C(10) C(15) 121.8(8) yes
C(11) C(10) C(15) 117.5(9) yes
C(10) C(11) C(12) 120.5(10) yes
C(10) C(11) H(8) 121(4) no
C(12) C(11) H(8) 117(4) no
C(11) C(12) C(13) 120.7(10) yes
C(11) C(12) H(9) 122(4) no
C(13) C(12) H(9) 116(4) no
C(12) C(13) C(14) 119.3(10) yes
C(12) C(13) H(10) 120(4) no
C(14) C(13) H(10) 119(5) no
C(13) C(14) C(15) 119(1) yes
C(13) C(14) H(11) 120(4) no
C(15) C(14) H(11) 119(5) no
C(10) C(15) C(14) 122.4(10) yes
C(10) C(15) H(12) 117(3) no
C(14) C(15) H(12) 119(3) no
C(8) C(16) C(17) 121.4(8) yes
C(8) C(16) H(13) 115(4) no
C(17) C(16) H(13) 123(4) no
C(16) C(17) C(18) 125.0(9) yes
C(16) C(17) C(22) 117.0(7) yes
C(18) C(17) C(22) 118.0(9) yes
C(17) C(18) C(19) 122.0(9) yes
C(17) C(18) H(14) 120(4) no
C(19) C(18) H(14) 117(4) no
C(18) C(19) C(20) 119.9(9) yes
C(18) C(19) H(15) 122(4) no
C(20) C(19) H(15) 117(3) no
C(19) C(20) C(21) 118.9(10) yes
C(19) C(20) H(16) 119(4) no
C(21) C(20) H(16) 121(4) no
C(20) C(21) C(22) 122.0(9) yes
C(20) C(21) H(17) 123(4) no
C(22) C(21) H(17) 114(4) no
N(1) C(22) C(17) 121.7(8) yes
N(1) C(22) C(21) 119.2(8) yes
C(17) C(22) C(21) 119.1(8) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N(1) C(1) 1.314(9) yes
N(1) C(22) 1.371(8) yes
C(1) C(2) 1.510(9) yes
C(1) C(8) 1.424(9) yes
C(2) C(3) 1.37(1) yes
C(2) C(7) 1.377(9) yes
C(3) C(4) 1.40(1) yes
C(3) H(1) 0.94(8) no
C(4) C(5) 1.37(1) yes
C(4) H(2) 1.1(1) no
C(5) C(6) 1.35(1) yes
C(5) H(3) 1.03(6) no
C(6) C(7) 1.39(1) yes
C(6) H(4) 1.05(9) no
C(7) H(5) 0.95(7) no
C(8) C(9) 1.50(1) yes
C(8) C(16) 1.357(10) yes
C(9) C(10) 1.51(1) yes
C(9) H(6) 1.05(7) no
C(9) H(7) 0.93(7) no
C(10) C(11) 1.38(1) yes
C(10) C(15) 1.38(1) yes
C(11) C(12) 1.39(1) yes
C(11) H(8) 0.98(8) no
C(12) C(13) 1.38(1) yes
C(12) H(9) 0.98(7) no
C(13) C(14) 1.37(1) yes
C(13) H(10) 0.98(8) no
C(14) C(15) 1.37(1) yes
C(14) H(11) 0.98(8) no
C(15) H(12) 0.95(4) no
C(16) C(17) 1.41(1) yes
C(16) H(13) 0.98(7) no
C(17) C(18) 1.39(1) yes
C(17) C(22) 1.423(9) yes
C(18) C(19) 1.37(1) yes
C(18) H(14) 0.94(7) no
C(19) C(20) 1.41(1) yes
C(19) H(15) 1.09(7) no
C(20) C(21) 1.36(1) yes
C(20) H(16) 0.99(8) no
C(21) C(22) 1.40(1) yes
C(21) H(17) 0.97(6) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
N(1) H(17) 2.78(6) 3_556
N(1) H(1) 2.86(9) 1_545
N(1) H(6) 3.20(7) 1_545
N(1) H(1) 3.30(8) 3_566
C(1) H(17) 3.41(7) 3_556
C(1) H(6) 3.46(8) 1_545
C(2) H(17) 3.16(7) 3_556
C(3) H(16) 3.26(7) 3_556
C(3) H(17) 3.32(7) 3_556
C(3) H(5) 3.45(7) 1_565
C(4) H(16) 2.88(8) 3_556
C(4) H(5) 3.31(7) 1_565
C(4) C(7) 3.55(1) 1_565
C(4) H(4) 3.57(8) 2_556
C(5) H(4) 2.91(8) 2_556
C(5) H(16) 3.01(7) 3_556
C(5) H(9) 3.22(7) 2_546
C(5) H(8) 3.30(7) 2_546
C(6) H(4) 3.02(9) 2_556
C(6) H(9) 3.17(7) 2_546
C(6) H(8) 3.32(7) 2_546
C(6) H(2) 3.3(1) 1_545
C(6) H(16) 3.43(7) 3_556
C(6) H(3) 3.53(6) 2_546
C(7) H(2) 3.2(1) 1_545
C(9) H(12) 3.59(5) 3_666
C(10) H(12) 3.51(5) 3_666
C(11) H(4) 3.09(9) 2_556
C(11) H(11) 3.14(9) 1_565
C(11) H(3) 3.36(7) 2_556
C(11) C(14) 3.51(1) 1_565
C(12) H(3) 3.11(7) 2_546
C(12) H(4) 3.20(9) 2_556
C(12) H(2) 3.4(1) 2_546
C(12) H(15) 3.44(7) 4_555
C(12) H(13) 3.46(7) 3_666
C(12) H(3) 3.48(7) 2_556
C(12) H(11) 3.48(9) 1_565
C(12) H(14) 3.55(7) 3_666
C(13) H(3) 2.87(7) 2_546
C(13) H(13) 2.98(7) 3_666
C(13) H(15) 3.54(7) 4_555
C(14) H(13) 2.86(8) 3_666
C(14) H(8) 3.10(8) 1_545
C(14) H(7) 3.17(7) 3_666
C(14) H(3) 3.39(7) 2_546
C(14) H(14) 3.54(7) 3_656
C(15) H(7) 3.22(7) 3_666
C(15) H(13) 3.25(7) 3_666
C(15) H(8) 3.45(8) 1_545
C(15) H(12) 3.52(5) 3_666
C(16) H(11) 3.53(9) 3_656
C(17) H(11) 3.41(8) 3_656
C(17) H(7) 3.58(7) 1_545
C(17) H(16) 3.58(7) 1_565
C(18) H(11) 3.08(8) 3_656
C(18) H(15) 3.26(8) 2_555
C(18) H(10) 3.43(8) 3_656
C(19) H(9) 3.20(7) 4_454
C(19) H(10) 3.39(8) 4_454
C(19) H(2) 3.4(1) 3_566
C(19) H(10) 3.47(7) 3_656
C(19) H(14) 3.57(7) 2_545
C(20) H(2) 2.9(1) 3_566
C(20) H(9) 3.16(7) 4_454
C(21) H(2) 2.9(1) 3_566
C(21) H(1) 3.30(8) 1_545
C(21) H(1) 3.37(9) 3_566
C(22) H(6) 3.38(7) 1_545
C(22) H(1) 3.41(9) 1_545
C(22) H(2) 3.4(1) 3_566
C(22) H(1) 3.47(8) 3_566
C(22) H(7) 3.59(7) 1_545
H(1) H(17) 2.8(1) 1_565
H(1) H(17) 3.0(1) 3_566
H(1) H(5) 3.5(1) 1_565
H(1) H(17) 3.5(1) 3_556
H(2) H(9) 2.9(1) 2_556
H(2) H(17) 3.0(1) 3_566
H(2) H(16) 3.1(1) 3_556
H(2) H(16) 3.1(1) 3_566
H(2) H(5) 3.3(1) 1_565
H(2) H(4) 3.3(1) 1_565
H(2) H(10) 3.4(1) 2_556
H(3) H(8) 2.6(1) 2_546
H(3) H(10) 2.88(10) 2_556
H(3) H(9) 2.9(1) 2_546
H(3) H(4) 3.0(1) 2_556
H(3) H(5) 3.07(9) 2_556
H(3) H(9) 3.2(1) 2_556
H(3) H(16) 3.28(9) 3_556
H(4) H(8) 2.6(1) 2_546
H(4) H(9) 2.9(1) 2_546
H(4) H(4) 3.18(8) 2_556
H(4) H(4) 3.18(8) 2_546
H(4) H(5) 3.4(1) 2_556
H(5) H(8) 2.8(1) 1_545
H(5) H(6) 2.9(1) 1_545
H(6) H(12) 3.59(9) 1_565
H(7) H(11) 2.9(1) 3_666
H(7) H(12) 2.89(8) 3_666
H(7) H(12) 3.16(9) 1_565
H(8) H(11) 3.0(1) 1_565
H(9) H(15) 2.83(10) 4_555
H(9) H(16) 2.9(1) 4_555
H(9) H(14) 3.45(10) 3_666
H(10) H(14) 3.0(1) 3_656
H(10) H(15) 3.1(1) 4_555
H(10) H(15) 3.15(10) 3_656
H(10) H(13) 3.3(1) 3_666
H(11) H(14) 2.8(1) 3_656
H(11) H(13) 3.1(1) 3_666
H(11) H(13) 3.4(1) 3_656
H(11) H(12) 3.41(10) 3_656
H(12) H(12) 3.35(10) 3_666
H(12) H(12) 3.49(10) 3_656
H(12) H(13) 3.57(8) 3_666
H(15) H(15) 3.43(8) 2_555
H(15) H(15) 3.43(8) 2_545
H(17) H(17) 3.4(1) 3_556
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_publ_flag
N(1) C(1) C(2) C(3) -100.1(9) yes
N(1) C(1) C(2) C(7) 79.4(8) yes
N(1) C(1) C(8) C(9) -177.1(7) yes
N(1) C(1) C(8) C(16) 0(1) yes
N(1) C(22) C(17) C(16) 2(1) yes
N(1) C(22) C(17) C(18) -179.7(7) yes
N(1) C(22) C(21) C(20) -179.5(8) yes
C(1) N(1) C(22) C(17) -2.5(10) yes
C(1) N(1) C(22) C(21) 178.3(7) yes
C(1) C(2) C(3) C(4) 179.3(8) yes
C(1) C(2) C(7) C(6) 179.6(7) yes
C(1) C(8) C(9) C(10) 77.1(10) yes
C(1) C(8) C(16) C(17) 0(1) yes
C(2) C(1) N(1) C(22) -178.8(7) yes
C(2) C(1) C(8) C(9) 3(1) yes
C(2) C(1) C(8) C(16) -179.8(8) yes
C(2) C(3) C(4) C(5) 1(1) yes
C(2) C(7) C(6) C(5) 0(1) yes
C(3) C(2) C(1) C(8) 79.7(9) yes
C(3) C(2) C(7) C(6) 0(1) yes
C(3) C(4) C(5) C(6) -1(1) yes
C(4) C(3) C(2) C(7) 0(1) yes
C(4) C(5) C(6) C(7) 0(1) yes
C(7) C(2) C(1) C(8) -100.8(9) yes
C(8) C(1) N(1) C(22) 1(1) yes
C(8) C(9) C(10) C(11) -139.5(8) yes
C(8) C(9) C(10) C(15) 39(1) yes
C(8) C(16) C(17) C(18) -178.7(8) yes
C(8) C(16) C(17) C(22) 0(1) yes
C(9) C(8) C(16) C(17) 176.6(8) yes
C(9) C(10) C(11) C(12) -179.5(8) yes
C(9) C(10) C(15) C(14) 179.6(8) yes
C(10) C(9) C(8) C(16) -99.8(9) yes
C(10) C(11) C(12) C(13) 0(1) yes
C(10) C(15) C(14) C(13) 0(1) yes
C(11) C(10) C(15) C(14) 0(1) yes
C(11) C(12) C(13) C(14) 0(1) yes
C(12) C(11) C(10) C(15) 0(1) yes
C(12) C(13) C(14) C(15) 0(1) yes
C(16) C(17) C(18) C(19) 177.5(9) yes
C(16) C(17) C(22) C(21) -178.7(7) yes
C(17) C(18) C(19) C(20) 0(1) yes
C(17) C(22) C(21) C(20) 1(1) yes
C(18) C(17) C(22) C(21) 0(1) yes
C(18) C(19) C(20) C(21) 0(1) yes
C(19) C(18) C(17) C(22) 0(1) yes
C(19) C(20) C(21) C(22) 0(1) yes
C(19) C(20) C(21) C(22) 0(1) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9776538
2 PubChem 11601781
