#------------------------------------------------------------------------------
#$Date: 2025-08-19 23:06:29 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301812 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/47/4024714.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_4024714
loop_
_publ_author_name
'Hua Yang'
'Rich G. Carter'
_publ_section_title
;
Asymmetric Construction of Nitrogen-Containing [2.2.2] Bicyclic Scaffolds
Using N-(p-Dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5151
_journal_page_last               5156
_journal_paper_doi               10.1021/jo9009062
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C19 H24 Cl N O'
_chemical_formula_weight         317.84
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXLTL
_cell_angle_alpha                90.00
_cell_angle_beta                 106.6770(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8419(9)
_cell_length_b                   7.8205(6)
_cell_length_c                   18.3084(14)
_cell_measurement_reflns_used    5770
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.40
_cell_volume                     1624.2(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18177
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.9585
_exptl_absorpt_correction_T_min  0.9194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cut-block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     589
_refine_ls_number_reflns         7035
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0451P)²+0.1345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0746
_reflns_number_gt                6827
_reflns_number_total             7035
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9009062_si_005.cif
_cod_data_source_block           rc44
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4024714
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.88073(3) 0.12023(5) 0.29861(2) 0.03390(9) Uani 1 1 d . . .
O1 O 0.97384(9) 0.93875(15) 0.03705(6) 0.0318(2) Uani 1 1 d . . .
N1 N 0.80308(11) 0.53974(16) 0.01873(7) 0.0260(3) Uani 1 1 d . . .
C1 C 0.73000(12) 0.69139(18) 0.00391(8) 0.0227(3) Uani 1 1 d . . .
C2 C 0.78622(12) 0.85116(19) 0.05170(8) 0.0249(3) Uani 1 1 d . . .
C3 C 0.86751(12) 0.93620(19) 0.01233(8) 0.0242(3) Uani 1 1 d . . .
C4 C 0.79978(14) 1.0140(2) -0.06290(9) 0.0294(3) Uani 1 1 d . . .
C5 C 0.67496(13) 0.93735(19) -0.08699(8) 0.0268(3) Uani 1 1 d . . .
C6 C 0.68249(11) 0.73789(19) -0.08290(7) 0.0227(3) Uani 1 1 d . . .
C7 C 0.60987(14) 1.0068(2) -0.03156(10) 0.0327(3) Uani 1 1 d . . .
C8 C 0.68468(13) 0.9748(2) 0.05150(9) 0.0292(3) Uani 1 1 d . . .
C9 C 0.56034(12) 0.65338(19) -0.11551(8) 0.0267(3) Uani 1 1 d . . .
C10 C 0.50612(13) 0.6845(2) -0.20065(9) 0.0305(3) Uani 1 1 d . . .
C11 C 0.58855(14) 0.6282(2) -0.24681(9) 0.0319(3) Uani 1 1 d . . .
C12 C 0.71151(14) 0.7043(2) -0.21549(9) 0.0292(3) Uani 1 1 d . . .
C13 C 0.76141(12) 0.6667(2) -0.13002(8) 0.0251(3) Uani 1 1 d . . .
C14 C 0.82238(11) 0.44992(18) 0.08665(8) 0.0224(3) Uani 1 1 d . . .
C15 C 0.91054(12) 0.32401(19) 0.10441(8) 0.0253(3) Uani 1 1 d . . .
C16 C 0.92961(13) 0.22369(19) 0.16881(8) 0.0269(3) Uani 1 1 d . . .
C17 C 0.85967(12) 0.2469(2) 0.21752(7) 0.0251(3) Uani 1 1 d . . .
C18 C 0.77338(13) 0.37102(18) 0.20195(8) 0.0254(3) Uani 1 1 d . . .
C19 C 0.75477(12) 0.47260(19) 0.13733(8) 0.0254(3) Uani 1 1 d . . .
Cl1' Cl 0.56877(3) 0.74573(5) -0.77675(2) 0.03665(10) Uani 1 1 d . . .
O1' O 0.93472(9) -0.03395(15) -0.53668(6) 0.0300(2) Uani 1 1 d . . .
N1' N 0.79766(11) 0.36263(16) -0.49383(7) 0.0256(2) Uani 1 1 d . . .
C1' C 0.74705(11) 0.20976(17) -0.47135(7) 0.0222(3) Uani 1 1 d . . .
C2' C 0.74603(12) 0.0524(2) -0.52363(8) 0.0256(3) Uani 1 1 d . . .
C3' C 0.86568(12) -0.03179(18) -0.49900(8) 0.0243(3) Uani 1 1 d . . .
C4' C 0.89111(15) -0.1103(2) -0.42065(9) 0.0297(3) Uani 1 1 d . . .
C5' C 0.80248(14) -0.0380(2) -0.38146(8) 0.0285(3) Uani 1 1 d . . .
C6' C 0.80230(12) 0.16121(18) -0.38522(8) 0.0223(3) Uani 1 1 d . . .
C7' C 0.68126(17) -0.1108(2) -0.42373(10) 0.0384(4) Uani 1 1 d . . .
C8' C 0.65377(14) -0.0740(2) -0.51016(9) 0.0324(3) Uani 1 1 d . . .
C9' C 0.72558(13) 0.2419(2) -0.33860(8) 0.0272(3) Uani 1 1 d . . .
C10' C 0.77402(15) 0.2095(2) -0.25271(9) 0.0310(3) Uani 1 1 d . . .
C11' C 0.90086(15) 0.2712(2) -0.22206(9) 0.0346(3) Uani 1 1 d . . .
C12' C 0.97933(14) 0.1960(2) -0.26666(8) 0.0315(3) Uani 1 1 d . . .
C13' C 0.92779(12) 0.2337(2) -0.35200(8) 0.0255(3) Uani 1 1 d . . .
C14' C 0.74121(12) 0.45048(18) -0.55959(8) 0.0223(3) Uani 1 1 d . . .
C15' C 0.62285(12) 0.4232(2) -0.60040(8) 0.0268(3) Uani 1 1 d . . .
C16' C 0.56986(13) 0.51859(19) -0.66523(8) 0.0258(3) Uani 1 1 d . . .
C17' C 0.63396(12) 0.63897(19) -0.69126(8) 0.0254(3) Uani 1 1 d . . .
C18' C 0.75087(12) 0.67078(19) -0.65156(8) 0.0258(3) Uani 1 1 d . . .
C19' C 0.80285(12) 0.57832(18) -0.58658(8) 0.0244(3) Uani 1 1 d . . .
H1N H 0.8580(17) 0.535(3) 0.0020(11) 0.033(5) Uiso 1 1 d . . .
H1'N H 0.8719(18) 0.368(3) -0.4806(11) 0.035(5) Uiso 1 1 d . . .
H1 H 0.6649(13) 0.6669(19) 0.0201(8) 0.011(3) Uiso 1 1 d . . .
H1' H 0.6651(14) 0.230(2) -0.4766(8) 0.021(4) Uiso 1 1 d . . .
H2 H 0.8307(14) 0.818(2) 0.1015(9) 0.020(4) Uiso 1 1 d . . .
H2' H 0.7290(14) 0.085(2) -0.5774(10) 0.029(4) Uiso 1 1 d . . .
H4A H 0.7965(16) 1.131(3) -0.0544(10) 0.036(5) Uiso 1 1 d . . .
H4B H 0.8394(16) 0.999(3) -0.1002(10) 0.032(5) Uiso 1 1 d . . .
H4C H 0.9766(17) -0.100(3) -0.3901(11) 0.035(5) Uiso 1 1 d . . .
H4D H 0.8780(18) -0.233(3) -0.4266(12) 0.049(6) Uiso 1 1 d . . .
H5 H 0.6352(15) 0.977(3) -0.1368(10) 0.030(4) Uiso 1 1 d . . .
H5' H 0.8235(15) -0.078(3) -0.3286(10) 0.033(5) Uiso 1 1 d . . .
H7A H 0.5294(17) 0.955(3) -0.0421(10) 0.036(5) Uiso 1 1 d . . .
H7B H 0.5994(18) 1.123(3) -0.0405(11) 0.046(5) Uiso 1 1 d . . .
H7C H 0.688(2) -0.237(4) -0.4147(13) 0.062(7) Uiso 1 1 d . . .
H7D H 0.6114(19) -0.057(3) -0.4080(12) 0.052(6) Uiso 1 1 d . . .
H8A H 0.6382(17) 0.923(3) 0.0826(10) 0.035(5) Uiso 1 1 d . . .
H8B H 0.7167(16) 1.075(3) 0.0787(10) 0.036(5) Uiso 1 1 d . . .
H8C H 0.6539(15) -0.179(3) -0.5384(10) 0.034(5) Uiso 1 1 d . . .
H8D H 0.5781(18) -0.024(3) -0.5307(11) 0.042(5) Uiso 1 1 d . . .
H9A H 0.5684(15) 0.532(3) -0.1060(10) 0.032(5) Uiso 1 1 d . . .
H9B H 0.5052(13) 0.691(2) -0.0866(8) 0.018(4) Uiso 1 1 d . . .
H9C H 0.7244(15) 0.369(2) -0.3491(10) 0.027(4) Uiso 1 1 d . . .
H9D H 0.6452(14) 0.198(2) -0.3593(9) 0.021(4) Uiso 1 1 d . . .
H10A H 0.4299(15) 0.621(3) -0.2183(10) 0.035(5) Uiso 1 1 d . . .
H10B H 0.4902(14) 0.808(2) -0.2105(9) 0.021(4) Uiso 1 1 d . . .
H10C H 0.7703(15) 0.087(2) -0.2406(10) 0.028(4) Uiso 1 1 d . . .
H10D H 0.7214(16) 0.270(3) -0.2262(11) 0.039(5) Uiso 1 1 d . . .
H11A H 0.5574(16) 0.660(3) -0.3036(11) 0.041(5) Uiso 1 1 d . . .
H11B H 0.5936(16) 0.509(3) -0.2459(11) 0.037(5) Uiso 1 1 d . . .
H11C H 0.9306(16) 0.251(3) -0.1690(11) 0.039(5) Uiso 1 1 d . . .
H11D H 0.9019(16) 0.397(3) -0.2290(10) 0.033(5) Uiso 1 1 d . . .
H12A H 0.7656(14) 0.657(2) -0.2411(9) 0.024(4) Uiso 1 1 d . . .
H12B H 0.7075(16) 0.828(3) -0.2261(11) 0.033(5) Uiso 1 1 d . . .
H12C H 1.0620(16) 0.241(3) -0.2488(10) 0.038(5) Uiso 1 1 d . . .
H12D H 0.9844(16) 0.064(3) -0.2570(10) 0.037(5) Uiso 1 1 d . . .
H13A H 0.8416(17) 0.715(3) -0.1109(10) 0.038(5) Uiso 1 1 d . . .
H13B H 0.7655(14) 0.541(2) -0.1225(9) 0.022(4) Uiso 1 1 d . . .
H13C H 0.9817(16) 0.188(3) -0.3807(10) 0.031(4) Uiso 1 1 d . . .
H13D H 0.9196(15) 0.351(3) -0.3588(10) 0.028(4) Uiso 1 1 d . . .
H15 H 0.9579(15) 0.307(2) 0.0693(10) 0.032(5) Uiso 1 1 d . . .
H15' H 0.5791(15) 0.342(3) -0.5829(10) 0.026(4) Uiso 1 1 d . . .
H16 H 0.9857(17) 0.136(3) 0.1776(10) 0.042(5) Uiso 1 1 d . . .
H16' H 0.4911(16) 0.500(2) -0.6924(9) 0.026(4) Uiso 1 1 d . . .
H18 H 0.7296(15) 0.386(2) 0.2359(10) 0.029(4) Uiso 1 1 d . . .
H18' H 0.7932(14) 0.758(3) -0.6678(9) 0.026(4) Uiso 1 1 d . . .
H19 H 0.6894(15) 0.567(2) 0.1282(10) 0.031(4) Uiso 1 1 d . . .
H19' H 0.8832(16) 0.597(3) -0.5585(10) 0.031(4) Uiso 1 1 d . . .
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C14 N1 C1 121.22(12) . . ?
C14 N1 H1N 112.3(14) . . ?
C1 N1 H1N 118.5(14) . . ?
N1 C1 C2 114.52(11) . . ?
N1 C1 C6 113.65(11) . . ?
C2 C1 C6 110.71(11) . . ?
N1 C1 H1 106.3(9) . . ?
C2 C1 H1 104.4(9) . . ?
C6 C1 H1 106.5(9) . . ?
C3 C2 C8 109.00(12) . . ?
C3 C2 C1 108.20(11) . . ?
C8 C2 C1 107.09(11) . . ?
C3 C2 H2 108.9(10) . . ?
C8 C2 H2 113.0(10) . . ?
C1 C2 H2 110.6(10) . . ?
O1 C3 C4 123.94(13) . . ?
O1 C3 C2 124.44(13) . . ?
C4 C3 C2 111.60(12) . . ?
C3 C4 C5 108.65(12) . . ?
C3 C4 H4A 106.4(11) . . ?
C5 C4 H4A 110.4(11) . . ?
C3 C4 H4B 111.5(11) . . ?
C5 C4 H4B 112.3(11) . . ?
H4A C4 H4B 107.5(16) . . ?
C4 C5 C7 107.18(13) . . ?
C4 C5 C6 109.79(12) . . ?
C7 C5 C6 110.68(12) . . ?
C4 C5 H5 108.7(11) . . ?
C7 C5 H5 108.4(11) . . ?
C6 C5 H5 112.0(12) . . ?
C9 C6 C13 106.20(11) . . ?
C9 C6 C5 111.96(11) . . ?
C13 C6 C5 111.59(12) . . ?
C9 C6 C1 108.41(11) . . ?
C13 C6 C1 112.55(11) . . ?
C5 C6 C1 106.19(11) . . ?
C5 C7 C8 109.75(12) . . ?
C5 C7 H7A 110.9(11) . . ?
C8 C7 H7A 111.6(11) . . ?
C5 C7 H7B 107.3(13) . . ?
C8 C7 H7B 110.0(12) . . ?
H7A C7 H7B 107.1(17) . . ?
C2 C8 C7 109.28(12) . . ?
C2 C8 H8A 107.7(11) . . ?
C7 C8 H8A 112.1(11) . . ?
C2 C8 H8B 108.9(11) . . ?
C7 C8 H8B 114.3(11) . . ?
H8A C8 H8B 104.2(16) . . ?
C10 C9 C6 113.54(12) . . ?
C10 C9 H9A 109.4(11) . . ?
C6 C9 H9A 108.5(11) . . ?
C10 C9 H9B 110.4(9) . . ?
C6 C9 H9B 110.7(9) . . ?
H9A C9 H9B 103.7(14) . . ?
C9 C10 C11 111.78(12) . . ?
C9 C10 H10A 109.1(10) . . ?
C11 C10 H10A 109.9(10) . . ?
C9 C10 H10B 110.1(9) . . ?
C11 C10 H10B 107.4(9) . . ?
H10A C10 H10B 108.5(15) . . ?
C12 C11 C10 111.86(13) . . ?
C12 C11 H11A 108.2(11) . . ?
C10 C11 H11A 112.8(11) . . ?
C12 C11 H11B 109.5(12) . . ?
C10 C11 H11B 109.0(12) . . ?
H11A C11 H11B 105.3(17) . . ?
C11 C12 C13 110.84(12) . . ?
C11 C12 H12A 111.3(10) . . ?
C13 C12 H12A 107.9(10) . . ?
C11 C12 H12B 108.8(11) . . ?
C13 C12 H12B 111.8(11) . . ?
H12A C12 H12B 106.2(15) . . ?
C12 C13 C6 112.50(12) . . ?
C12 C13 H13A 109.8(11) . . ?
C6 C13 H13A 109.7(11) . . ?
C12 C13 H13B 108.7(9) . . ?
C6 C13 H13B 107.0(9) . . ?
H13A C13 H13B 109.0(15) . . ?
N1 C14 C19 123.43(13) . . ?
N1 C14 C15 118.86(12) . . ?
C19 C14 C15 117.65(13) . . ?
C16 C15 C14 121.69(13) . . ?
C16 C15 H15 120.2(11) . . ?
C14 C15 H15 118.1(11) . . ?
C15 C16 C17 119.45(13) . . ?
C15 C16 H16 119.8(12) . . ?
C17 C16 H16 120.7(12) . . ?
C18 C17 C16 120.08(13) . . ?
C18 C17 Cl1 119.53(11) . . ?
C16 C17 Cl1 120.38(11) . . ?
C17 C18 C19 120.38(13) . . ?
C17 C18 H18 118.3(11) . . ?
C19 C18 H18 121.3(11) . . ?
C18 C19 C14 120.73(13) . . ?
C18 C19 H19 117.9(9) . . ?
C14 C19 H19 121.3(9) . . ?
C14' N1' C1' 121.48(12) . . ?
C14' N1' H1'N 115.6(14) . . ?
C1' N1' H1'N 116.0(14) . . ?
N1' C1' C2' 114.09(11) . . ?
N1' C1' C6' 113.43(11) . . ?
C2' C1' C6' 110.72(11) . . ?
N1' C1' H1' 109.0(10) . . ?
C2' C1' H1' 103.8(10) . . ?
C6' C1' H1' 104.9(9) . . ?
C3' C2' C8' 108.62(13) . . ?
C3' C2' C1' 108.68(11) . . ?
C8' C2' C1' 106.78(11) . . ?
C3' C2' H2' 108.5(10) . . ?
C8' C2' H2' 112.0(10) . . ?
C1' C2' H2' 112.2(11) . . ?
O1' C3' C4' 123.52(13) . . ?
O1' C3' C2' 124.40(13) . . ?
C4' C3' C2' 112.06(12) . . ?
C3' C4' C5' 108.48(12) . . ?
C3' C4' H4C 112.9(11) . . ?
C5' C4' H4C 114.9(11) . . ?
C3' C4' H4D 108.2(12) . . ?
C5' C4' H4D 107.8(12) . . ?
H4C C4' H4D 104.2(17) . . ?
C7' C5' C4' 107.07(13) . . ?
C7' C5' C6' 111.10(14) . . ?
C4' C5' C6' 109.81(12) . . ?
C7' C5' H5' 108.5(11) . . ?
C4' C5' H5' 109.3(11) . . ?
C6' C5' H5' 110.9(12) . . ?
C13' C6' C9' 106.51(11) . . ?
C13' C6' C5' 111.14(12) . . ?
C9' C6' C5' 112.11(11) . . ?
C13' C6' C1' 112.55(10) . . ?
C9' C6' C1' 108.28(11) . . ?
C5' C6' C1' 106.30(11) . . ?
C5' C7' C8' 109.81(12) . . ?
C5' C7' H7C 105.4(13) . . ?
C8' C7' H7C 109.6(13) . . ?
C5' C7' H7D 114.3(13) . . ?
C8' C7' H7D 104.9(12) . . ?
H7C C7' H7D 112.8(19) . . ?
C2' C8' C7' 109.34(12) . . ?
C2' C8' H8C 110.3(11) . . ?
C7' C8' H8C 110.8(11) . . ?
C2' C8' H8D 107.8(13) . . ?
C7' C8' H8D 112.2(12) . . ?
H8C C8' H8D 106.3(17) . . ?
C10' C9' C6' 113.10(12) . . ?
C10' C9' H9C 109.7(10) . . ?
C6' C9' H9C 105.9(10) . . ?
C10' C9' H9D 112.0(9) . . ?
C6' C9' H9D 107.7(9) . . ?
H9C C9' H9D 108.0(14) . . ?
C11' C10' C9' 111.39(12) . . ?
C11' C10' H10C 109.1(10) . . ?
C9' C10' H10C 111.3(10) . . ?
C11' C10' H10D 110.6(11) . . ?
C9' C10' H10D 108.2(11) . . ?
H10C C10' H10D 106.0(15) . . ?
C12' C11' C10' 111.68(13) . . ?
C12' C11' H11C 112.4(12) . . ?
C10' C11' H11C 111.2(12) . . ?
C12' C11' H11D 106.5(11) . . ?
C10' C11' H11D 108.3(11) . . ?
H11C C11' H11D 106.4(18) . . ?
C11' C12' C13' 110.29(13) . . ?
C11' C12' H12C 112.3(11) . . ?
C13' C12' H12C 109.3(11) . . ?
C11' C12' H12D 107.8(11) . . ?
C13' C12' H12D 110.4(10) . . ?
H12C C12' H12D 106.7(16) . . ?
C12' C13' C6' 112.79(12) . . ?
C12' C13' H13C 109.8(10) . . ?
C6' C13' H13C 110.4(10) . . ?
C12' C13' H13D 108.8(11) . . ?
C6' C13' H13D 105.0(11) . . ?
H13C C13' H13D 109.9(16) . . ?
N1' C14' C15' 123.27(12) . . ?
N1' C14' C19' 119.29(12) . . ?
C15' C14' C19' 117.40(13) . . ?
C16' C15' C14' 120.72(13) . . ?
C16' C15' H15' 119.9(10) . . ?
C14' C15' H15' 119.3(10) . . ?
C17' C16' C15' 120.24(13) . . ?
C17' C16' H16' 119.1(10) . . ?
C15' C16' H16' 120.6(11) . . ?
C16' C17' C18' 120.46(13) . . ?
C16' C17' Cl1' 119.41(11) . . ?
C18' C17' Cl1' 120.08(11) . . ?
C19' C18' C17' 119.29(13) . . ?
C19' C18' H18' 120.3(10) . . ?
C17' C18' H18' 120.3(10) . . ?
C18' C19' C14' 121.84(13) . . ?
C18' C19' H19' 120.9(11) . . ?
C14' C19' H19' 117.2(11) . . ?
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
Cl1 C17 1.7421(14) . ?
O1 C3 1.2098(17) . ?
N1 C14 1.3888(18) . ?
N1 C1 1.4471(18) . ?
N1 H1N 0.80(2) . ?
C1 C2 1.561(2) . ?
C1 C6 1.5689(18) . ?
C1 H1 0.922(14) . ?
C2 C3 1.5123(19) . ?
C2 C8 1.542(2) . ?
C2 H2 0.947(17) . ?
C3 C4 1.509(2) . ?
C4 C5 1.538(2) . ?
C4 H4A 0.93(2) . ?
C4 H4B 0.941(19) . ?
C5 C7 1.539(2) . ?
C5 C6 1.563(2) . ?
C5 H5 0.949(18) . ?
C6 C9 1.5460(19) . ?
C6 C13 1.5461(19) . ?
C7 C8 1.545(2) . ?
C7 H7A 1.00(2) . ?
C7 H7B 0.93(3) . ?
C8 H8A 0.986(19) . ?
C8 H8B 0.95(2) . ?
C9 C10 1.525(2) . ?
C9 H9A 0.96(2) . ?
C9 H9B 0.995(16) . ?
C10 C11 1.528(2) . ?
C10 H10A 0.999(19) . ?
C10 H10B 0.994(18) . ?
C11 C12 1.524(2) . ?
C11 H11A 1.028(19) . ?
C11 H11B 0.93(2) . ?
C12 C13 1.534(2) . ?
C12 H12A 0.968(17) . ?
C12 H12B 0.98(2) . ?
C13 H13A 0.99(2) . ?
C13 H13B 0.994(17) . ?
C14 C19 1.4000(19) . ?
C14 C15 1.4037(19) . ?
C15 C16 1.380(2) . ?
C15 H15 0.975(18) . ?
C16 C17 1.392(2) . ?
C16 H16 0.93(2) . ?
C17 C18 1.379(2) . ?
C18 C19 1.389(2) . ?
C18 H18 0.924(18) . ?
C19 H19 1.048(18) . ?
Cl1' C17' 1.7463(14) . ?
O1' C3' 1.2116(17) . ?
N1' C14' 1.3806(18) . ?
N1' C1' 1.4489(18) . ?
N1' H1'N 0.84(2) . ?
C1' C2' 1.557(2) . ?
C1' C6' 1.5706(18) . ?
C1' H1' 0.960(16) . ?
C2' C3' 1.5093(19) . ?
C2' C8' 1.545(2) . ?
C2' H2' 0.979(17) . ?
C3' C4' 1.509(2) . ?
C4' C5' 1.539(2) . ?
C4' H4C 1.010(19) . ?
C4' H4D 0.98(2) . ?
C5' C7' 1.532(2) . ?
C5' C6' 1.559(2) . ?
C5' H5' 0.977(19) . ?
C6' C13' 1.5430(19) . ?
C6' C9' 1.5481(19) . ?
C7' C8' 1.548(2) . ?
C7' H7C 1.00(3) . ?
C7' H7D 1.04(2) . ?
C8' H8C 0.97(2) . ?
C8' H8D 0.95(2) . ?
C9' C10' 1.532(2) . ?
C9' H9C 1.014(19) . ?
C9' H9D 0.980(17) . ?
C10' C11' 1.523(2) . ?
C10' H10C 0.985(19) . ?
C10' H10D 1.01(2) . ?
C11' C12' 1.521(2) . ?
C11' H11C 0.95(2) . ?
C11' H11D 0.99(2) . ?
C12' C13' 1.534(2) . ?
C12' H12C 1.002(19) . ?
C12' H12D 1.04(2) . ?
C13' H13C 1.001(18) . ?
C13' H13D 0.93(2) . ?
C14' C15' 1.4026(19) . ?
C14' C19' 1.4084(19) . ?
C15' C16' 1.390(2) . ?
C15' H15' 0.931(19) . ?
C16' C17' 1.377(2) . ?
C16' H16' 0.934(18) . ?
C17' C18' 1.389(2) . ?
C18' C19' 1.377(2) . ?
C18' H18' 0.941(18) . ?
C19' H19' 0.955(18) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.80(2) 2.42(2) 3.1927(16) 163.9(19) 2_745
N1' H1'N O1' 0.84(2) 2.35(2) 3.1614(16) 161.7(19) 2_754
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
C14 N1 C1 C2 71.55(16) . . . . ?
C14 N1 C1 C6 -159.84(13) . . . . ?
N1 C1 C2 C3 82.82(14) . . . . ?
C6 C1 C2 C3 -47.26(14) . . . . ?
N1 C1 C2 C8 -159.82(11) . . . . ?
C6 C1 C2 C8 70.10(13) . . . . ?
C8 C2 C3 O1 133.17(15) . . . . ?
C1 C2 C3 O1 -110.71(16) . . . . ?
C8 C2 C3 C4 -48.29(16) . . . . ?
C1 C2 C3 C4 67.83(15) . . . . ?
O1 C3 C4 C5 161.79(14) . . . . ?
C2 C3 C4 C5 -16.76(17) . . . . ?
C3 C4 C5 C7 69.40(16) . . . . ?
C3 C4 C5 C6 -50.86(16) . . . . ?
C4 C5 C6 C9 -173.29(11) . . . . ?
C7 C5 C6 C9 68.59(15) . . . . ?
C4 C5 C6 C13 -54.40(15) . . . . ?
C7 C5 C6 C13 -172.52(11) . . . . ?
C4 C5 C6 C1 68.57(14) . . . . ?
C7 C5 C6 C1 -49.55(15) . . . . ?
N1 C1 C6 C9 92.53(14) . . . . ?
C2 C1 C6 C9 -136.94(12) . . . . ?
N1 C1 C6 C13 -24.64(16) . . . . ?
C2 C1 C6 C13 105.89(13) . . . . ?
N1 C1 C6 C5 -147.01(12) . . . . ?
C2 C1 C6 C5 -16.47(14) . . . . ?
C4 C5 C7 C8 -52.17(17) . . . . ?
C6 C5 C7 C8 67.53(16) . . . . ?
C3 C2 C8 C7 64.50(16) . . . . ?
C1 C2 C8 C7 -52.34(16) . . . . ?
C5 C7 C8 C2 -11.99(18) . . . . ?
C13 C6 C9 C10 -56.97(16) . . . . ?
C5 C6 C9 C10 65.05(16) . . . . ?
C1 C6 C9 C10 -178.14(12) . . . . ?
C6 C9 C10 C11 55.11(18) . . . . ?
C9 C10 C11 C12 -51.47(18) . . . . ?
C10 C11 C12 C13 53.06(18) . . . . ?
C11 C12 C13 C6 -58.53(17) . . . . ?
C9 C6 C13 C12 58.56(15) . . . . ?
C5 C6 C13 C12 -63.69(15) . . . . ?
C1 C6 C13 C12 177.04(12) . . . . ?
C1 N1 C14 C19 14.8(2) . . . . ?
C1 N1 C14 C15 -168.19(13) . . . . ?
N1 C14 C15 C16 -176.28(14) . . . . ?
C19 C14 C15 C16 0.9(2) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
C15 C16 C17 C18 -1.0(2) . . . . ?
C15 C16 C17 Cl1 179.23(11) . . . . ?
C16 C17 C18 C19 0.6(2) . . . . ?
Cl1 C17 C18 C19 -179.61(11) . . . . ?
C17 C18 C19 C14 0.5(2) . . . . ?
N1 C14 C19 C18 175.76(14) . . . . ?
C15 C14 C19 C18 -1.3(2) . . . . ?
C14' N1' C1' C2' 69.52(16) . . . . ?
C14' N1' C1' C6' -162.44(12) . . . . ?
N1' C1' C2' C3' 82.35(14) . . . . ?
C6' C1' C2' C3' -47.06(14) . . . . ?
N1' C1' C2' C8' -160.65(12) . . . . ?
C6' C1' C2' C8' 69.93(14) . . . . ?
C8' C2' C3' O1' 132.19(15) . . . . ?
C1' C2' C3' O1' -111.99(15) . . . . ?
C8' C2' C3' C4' -49.13(16) . . . . ?
C1' C2' C3' C4' 66.68(15) . . . . ?
O1' C3' C4' C5' 163.31(14) . . . . ?
C2' C3' C4' C5' -15.38(17) . . . . ?
C3' C4' C5' C7' 69.03(16) . . . . ?
C3' C4' C5' C6' -51.69(17) . . . . ?
C7' C5' C6' C13' -172.55(11) . . . . ?
C4' C5' C6' C13' -54.29(15) . . . . ?
C7' C5' C6' C9' 68.37(15) . . . . ?
C4' C5' C6' C9' -173.37(12) . . . . ?
C7' C5' C6' C1' -49.77(14) . . . . ?
C4' C5' C6' C1' 68.49(15) . . . . ?
N1' C1' C6' C13' -24.07(16) . . . . ?
C2' C1' C6' C13' 105.70(13) . . . . ?
N1' C1' C6' C9' 93.40(13) . . . . ?
C2' C1' C6' C9' -136.84(12) . . . . ?
N1' C1' C6' C5' -145.96(12) . . . . ?
C2' C1' C6' C5' -16.20(14) . . . . ?
C4' C5' C7' C8' -53.41(18) . . . . ?
C6' C5' C7' C8' 66.50(17) . . . . ?
C3' C2' C8' C7' 63.69(16) . . . . ?
C1' C2' C8' C7' -53.34(16) . . . . ?
C5' C7' C8' C2' -10.54(19) . . . . ?
C13' C6' C9' C10' -56.27(16) . . . . ?
C5' C6' C9' C10' 65.50(16) . . . . ?
C1' C6' C9' C10' -177.55(12) . . . . ?
C6' C9' C10' C11' 55.64(18) . . . . ?
C9' C10' C11' C12' -53.44(19) . . . . ?
C10' C11' C12' C13' 54.65(18) . . . . ?
C11' C12' C13' C6' -58.77(18) . . . . ?
C9' C6' C13' C12' 58.00(16) . . . . ?
C5' C6' C13' C12' -64.38(16) . . . . ?
C1' C6' C13' C12' 176.51(12) . . . . ?
C1' N1' C14' C15' 14.0(2) . . . . ?
C1' N1' C14' C19' -168.23(13) . . . . ?
N1' C14' C15' C16' 178.39(13) . . . . ?
C19' C14' C15' C16' 0.5(2) . . . . ?
C14' C15' C16' C17' 1.4(2) . . . . ?
C15' C16' C17' C18' -2.3(2) . . . . ?
C15' C16' C17' Cl1' 175.19(11) . . . . ?
C16' C17' C18' C19' 1.2(2) . . . . ?
Cl1' C17' C18' C19' -176.28(11) . . . . ?
C17' C18' C19' C14' 0.8(2) . . . . ?
N1' C14' C19' C18' -179.60(13) . . . . ?
C15' C14' C19' C18' -1.7(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139091196
