#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:25:50 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180298 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/12/7151294.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_7151294
loop_
_publ_author_name
'Wang, Xiaowei'
'Lou, Qinghua'
'Guo, Ying'
'Xu, Yang'
'Zhang, Zhili'
'Liu, Junyi'
_publ_section_title
;
 The design and synthesis of 9-phenylcyclohepta[d]pyrimidine-2,4-dione
 derivatives as potent non-nucleoside inhibitors of HIV reverse
 transcriptase.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3252
_journal_page_last               3258
_journal_paper_doi               10.1039/b607972p
_journal_volume                  4
_journal_year                    2006
_chemical_formula_sum            'C18 H22 N2 O3'
_chemical_formula_weight         314.38
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   'geom or difmap'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                114.849(3)
_cell_angle_beta                 101.576(3)
_cell_angle_gamma                99.321(3)
_cell_formula_units_Z            2
_cell_length_a                   8.2013(12)
_cell_length_b                   10.5938(16)
_cell_length_c                   10.9160(17)
_cell_measurement_temperature    293(2)
_cell_volume                     810.1(2)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.0142
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4162
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.974
_exptl_crystal_colour            no
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0741P)²+0.1482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1487
_reflns_number_gt                2542
_reflns_number_total             3286
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b607972p.txt
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151294
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.3447(2) 0.3855(2) 0.56134(19) 0.0572(5) Uani 1 1 d . . .
H1 H 0.3651 0.3888 0.4818 0.069 Uiso 1 1 calc R . .
C2 C 0.4378(3) 0.4975(2) 0.6943(2) 0.0671(6) Uani 1 1 d . . .
H2 H 0.5197 0.5751 0.7031 0.081 Uiso 1 1 calc R . .
C3 C 0.4106(3) 0.4954(2) 0.8130(2) 0.0658(5) Uani 1 1 d . . .
H3 H 0.4724 0.5716 0.9021 0.079 Uiso 1 1 calc R . .
C4 C 0.2913(3) 0.3797(2) 0.7991(2) 0.0654(5) Uani 1 1 d . . .
H4 H 0.2730 0.3765 0.8792 0.078 Uiso 1 1 calc R . .
C5 C 0.1983(2) 0.2680(2) 0.66635(19) 0.0562(5) Uani 1 1 d . . .
H5 H 0.1176 0.1902 0.6584 0.067 Uiso 1 1 calc R . .
C6 C 0.2223(2) 0.26915(17) 0.54477(17) 0.0444(4) Uani 1 1 d . . .
C7 C 0.1126(2) 0.14353(17) 0.40082(17) 0.0456(4) Uani 1 1 d . . .
H7 H 0.1231 0.0559 0.4080 0.055 Uiso 1 1 calc R . .
C8 C -0.0820(2) 0.13372(19) 0.3719(2) 0.0560(5) Uani 1 1 d . . .
H8A H -0.1421 0.0581 0.2760 0.067 Uiso 1 1 calc R . .
H8B H -0.1242 0.1038 0.4352 0.067 Uiso 1 1 calc R . .
C9 C -0.1310(3) 0.2699(2) 0.3888(2) 0.0678(5) Uani 1 1 d . . .
H9A H -0.1084 0.3339 0.4898 0.080 Uiso 0.732(7) 1 d P . .
H9B H -0.2562 0.2447 0.3459 0.080 Uiso 0.732(7) 1 d P . .
H9C H -0.0476 0.3558 0.4679 0.080 Uiso 0.268(7) 1 d P . .
H9D H -0.2454 0.2673 0.4041 0.080 Uiso 0.268(7) 1 d P . .
C10A C -0.0405(4) 0.3545(3) 0.3256(3) 0.0591(10) Uani 0.732(7) 1 d P . .
H10A H -0.1019 0.4225 0.3168 0.080 Uiso 0.732(7) 1 d P . .
H10B H 0.0765 0.4105 0.3893 0.080 Uiso 0.732(7) 1 d P . .
C10B C -0.1341(13) 0.2673(10) 0.2442(10) 0.068(3) Uani 0.268(7) 1 d P . .
H10C H -0.1925 0.1697 0.1656 0.080 Uiso 0.268(7) 1 d P . .
H10D H -0.1987 0.3316 0.2282 0.080 Uiso 0.268(7) 1 d P . .
C11A C -0.0272(5) 0.2535(4) 0.1817(4) 0.0568(9) Uani 0.732(7) 1 d P . .
H11A H -0.0173 0.3059 0.1276 0.080 Uiso 0.732(7) 1 d P . .
H11B H -0.1358 0.1757 0.1299 0.080 Uiso 0.732(7) 1 d P . .
C11B C 0.0444(17) 0.3113(11) 0.2379(12) 0.065(3) Uani 0.268(7) 1 d P . .
H11C H 0.1160 0.3851 0.3317 0.080 Uiso 0.268(7) 1 d P . .
H11D H 0.0429 0.3544 0.1747 0.080 Uiso 0.268(7) 1 d P . .
C12 C 0.1245(2) 0.18607(18) 0.18861(19) 0.0528(4) Uani 1 1 d . . .
C13 C 0.1824(2) 0.13557(16) 0.27978(16) 0.0437(4) Uani 1 1 d . . .
C14 C 0.3895(2) 0.04513(19) 0.15829(18) 0.0511(4) Uani 1 1 d . . .
C15 C 0.2000(3) 0.16554(18) 0.07365(19) 0.0554(5) Uani 1 1 d . . .
C16 C 0.3855(2) 0.0145(2) 0.36450(19) 0.0544(4) Uani 1 1 d . . .
H16A H 0.4980 0.0015 0.3568 0.065 Uiso 1 1 calc R . .
H16B H 0.4019 0.0873 0.4604 0.065 Uiso 1 1 calc R . .
C17 C 0.2819(4) -0.2401(3) 0.2177(3) 0.0896(8) Uani 1 1 d . . .
H17A H 0.4006 -0.2436 0.2240 0.107 Uiso 1 1 calc R . .
H17B H 0.2345 -0.2322 0.1332 0.107 Uiso 1 1 calc R . .
C18 C 0.1816(4) -0.3720(3) 0.2075(4) 0.1164(11) Uani 1 1 d . . .
H18A H 0.1846 -0.4538 0.1250 0.175 Uiso 1 1 calc R . .
H18B H 0.0639 -0.3689 0.2004 0.175 Uiso 1 1 calc R . .
H18C H 0.2300 -0.3808 0.2903 0.175 Uiso 1 1 calc R . .
N1 N 0.3295(2) 0.09784(16) 0.06953(15) 0.0524(4) Uani 1 1 d . . .
HN1 H 0.375(3) 0.078(2) -0.002(2) 0.061(6) Uiso 1 1 d . . .
N2 N 0.31617(18) 0.06776(15) 0.26579(14) 0.0471(3) Uani 1 1 d . . .
O1 O 0.1567(2) 0.20399(18) -0.01591(17) 0.0851(5) Uani 1 1 d . . .
O2 O 0.50140(18) -0.01890(18) 0.14269(15) 0.0704(4) Uani 1 1 d . . .
O3 O 0.27918(18) -0.11538(14) 0.34017(14) 0.0621(4) Uani 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'
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
C6 C1 C2 121.09(17) . . ?
C6 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C3 C2 C1 120.66(19) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.26(18) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 120.04(17) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 121.56(18) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 117.38(16) . . ?
C1 C6 C7 123.65(14) . . ?
C5 C6 C7 118.97(15) . . ?
C13 C7 C6 113.68(13) . . ?
C13 C7 C8 114.11(15) . . ?
C6 C7 C8 112.60(13) . . ?
C13 C7 H7 105.1 . . ?
C6 C7 H7 105.1 . . ?
C8 C7 H7 105.1 . . ?
C9 C8 C7 116.39(15) . . ?
C9 C8 H8A 108.2 . . ?
C7 C8 H8A 108.2 . . ?
C9 C8 H8B 108.2 . . ?
C7 C8 H8B 108.2 . . ?
H8A C8 H8B 107.3 . . ?
C8 C9 C10A 116.23(17) . . ?
C8 C9 C10B 102.7(3) . . ?
C10A C9 C10B 38.5(3) . . ?
C8 C9 H9A 108.5(2) . . ?
C10A C9 H9A 108.7(2) . . ?
C10B C9 H9A 143.7(4) . . ?
C8 C9 H9B 108.52(19) . . ?
C10A C9 H9B 108.3(2) . . ?
C10B C9 H9B 80.3(4) . . ?
H9A C9 H9B 106.07(18) . . ?
C8 C9 H9C 111.94(19) . . ?
C10A C9 H9C 73.43(18) . . ?
C10B C9 H9C 111.8(4) . . ?
H9A C9 H9C 38.65(9) . . ?
H9B C9 H9C 133.2(2) . . ?
C8 C9 H9D 111.13(19) . . ?
C10A C9 H9D 127.8(2) . . ?
C10B C9 H9D 111.2(4) . . ?
H9A C9 H9D 74.22(14) . . ?
H9B C9 H9D 33.05(7) . . ?
H9C C9 H9D 108.0(2) . . ?
C10B C10A C11B 80.2(8) . . ?
C10B C10A C11A 52.2(5) . . ?
C11B C10A C11A 28.1(5) . . ?
C10B C10A C9 72.4(6) . . ?
C11B C10A C9 127.7(5) . . ?
C11A C10A C9 111.4(3) . . ?
C10B C10A H9C 109.0(6) . . ?
C11B C10A H9C 137.6(5) . . ?
C11A C10A H9C 139.8(2) . . ?
C9 C10A H9C 36.60(11) . . ?
C10B C10A H10A 93.1(5) . . ?
C11B C10A H10A 115.0(5) . . ?
C11A C10A H10A 109.8(3) . . ?
C9 C10A H10A 110.4(2) . . ?
H9C C10A H10A 106.0(2) . . ?
C10B C10A H10B 156.6(5) . . ?
C11B C10A H10B 81.0(7) . . ?
C11A C10A H10B 108.6(3) . . ?
C9 C10A H10B 109.2(2) . . ?
H9C C10A H10B 76.60(19) . . ?
H10A C10A H10B 107.4(3) . . ?
C10B C10A H10D 43.7(5) . . ?
C11B C10A H10D 97.9(7) . . ?
C11A C10A H10D 75.4(2) . . ?
C9 C10A H10D 92.11(19) . . ?
H9C C10A H10D 117.61(19) . . ?
H10A C10A H10D 49.41(14) . . ?
H10B C10A H10D 154.1(3) . . ?
C10B C10A H11C 124.6(6) . . ?
C11B C10A H11C 45.2(6) . . ?
C11A C10A H11C 73.2(2) . . ?
C9 C10A H11C 129.1(2) . . ?
H9C C10A H11C 107.2(2) . . ?
H10A C10A H11C 115.2(3) . . ?
H10B C10A H11C 35.86(10) . . ?
H10D C10A H11C 135.0(2) . . ?
C10A C10B C11A 85.9(8) . . ?
C10A C10B C11B 57.3(7) . . ?
C11A C10B C11B 28.7(4) . . ?
C10A C10B C9 69.1(6) . . ?
C11A C10B C9 130.9(7) . . ?
C11B C10B C9 111.2(8) . . ?
C10A C10B H10A 42.1(4) . . ?
C11A C10B H10A 101.9(7) . . ?
C11B C10B H10A 80.6(7) . . ?
C9 C10B H10A 87.3(5) . . ?
C10A C10B H10C 161.5(9) . . ?
C11A C10B H10C 80.9(7) . . ?
C11B C10B H10C 108.4(8) . . ?
C9 C10B H10C 110.5(7) . . ?
H10A C10B H10C 154.2(9) . . ?
C10A C10B H10D 90.1(7) . . ?
C11A C10B H10D 110.4(8) . . ?
C11B C10B H10D 108.8(8) . . ?
C9 C10B H10D 111.2(7) . . ?
H10A C10B H10D 48.1(4) . . ?
H10C C10B H10D 106.6(9) . . ?
C10A C10B H11B 133.6(9) . . ?
C11A C10B H11B 47.8(4) . . ?
C11B C10B H11B 76.3(7) . . ?
C9 C10B H11B 134.4(6) . . ?
H10A C10B H11B 137.4(7) . . ?
H10C C10B H11B 33.8(3) . . ?
H10D C10B H11B 107.9(8) . . ?
C11B C11A C10B 97.9(12) . . ?
C11B C11A C10A 56.1(10) . . ?
C10B C11A C10A 41.9(5) . . ?
C11B C11A C12 75.0(10) . . ?
C10B C11A C12 131.7(5) . . ?
C10A C11A C12 114.3(3) . . ?
C11B C11A H10C 138.2(11) . . ?
C10B C11A H10C 42.7(5) . . ?
C10A C11A H10C 83.9(2) . . ?
C12 C11A H10C 117.2(2) . . ?
C11B C11A H11A 87.3(10) . . ?
C10B C11A H11A 118.3(5) . . ?
C10A C11A H11A 109.2(3) . . ?
C12 C11A H11A 109.2(3) . . ?
H10C C11A H11A 120.4(3) . . ?
C11B C11A H11B 162.5(11) . . ?
C10B C11A H11B 66.5(6) . . ?
C10A C11A H11B 108.2(3) . . ?
C12 C11A H11B 108.9(3) . . ?
H10C C11A H11B 24.69(11) . . ?
H11A C11A H11B 106.7(4) . . ?
C11B C11A H11D 56.2(9) . . ?
C10B C11A H11D 117.8(5) . . ?
C10A C11A H11D 89.2(3) . . ?
C12 C11A H11D 98.0(3) . . ?
H10C C11A H11D 143.8(3) . . ?
H11A C11A H11D 31.13(12) . . ?
H11B C11A H11D 137.1(3) . . ?
C11A C11B C10A 95.8(13) . . ?
C11A C11B C10B 53.4(11) . . ?
C10A C11B C10B 42.5(5) . . ?
C11A C11B C12 77.7(9) . . ?
C10A C11B C12 134.1(8) . . ?
C10B C11B C12 112.9(8) . . ?
C11A C11B H10B 135.8(14) . . ?
C10A C11B H10B 40.9(4) . . ?
C10B C11B H10B 82.6(7) . . ?
C12 C11B H10B 122.3(8) . . ?
C11A C11B H11A 55.2(9) . . ?
C10A C11B H11A 114.0(10) . . ?
C10B C11B H11A 88.3(10) . . ?
C12 C11B H11A 99.3(7) . . ?
H10B C11B H11A 137.7(8) . . ?
C11A C11B H11C 161.0(16) . . ?
C10A C11B H11C 66.5(6) . . ?
C10B C11B H11C 108.3(9) . . ?
C12 C11B H11C 109.2(10) . . ?
H10B C11B H11C 25.7(3) . . ?
H11A C11B H11C 137.0(10) . . ?
C11A C11B H11D 85.9(12) . . ?
C10A C11B H11D 115.6(9) . . ?
C10B C11B H11D 109.6(11) . . ?
C12 C11B H11D 109.2(8) . . ?
H10B C11B H11D 117.0(8) . . ?
H11A C11B H11D 30.7(3) . . ?
H11C C11B H11D 107.5(10) . . ?
C13 C12 C15 119.10(17) . . ?
C13 C12 C11B 119.0(4) . . ?
C15 C12 C11B 117.1(4) . . ?
C13 C12 C11A 127.54(19) . . ?
C15 C12 C11A 113.12(19) . . ?
C11B C12 C11A 27.3(4) . . ?
C12 C13 N2 120.41(15) . . ?
C12 C13 C7 125.35(15) . . ?
N2 C13 C7 114.24(14) . . ?
O2 C14 N1 121.83(15) . . ?
O2 C14 N2 122.38(17) . . ?
N1 C14 N2 115.79(16) . . ?
O1 C15 N1 119.21(17) . . ?
O1 C15 C12 125.05(19) . . ?
N1 C15 C12 115.74(16) . . ?
O3 C16 N2 113.60(14) . . ?
O3 C16 H16A 108.8 . . ?
N2 C16 H16A 108.8 . . ?
O3 C16 H16B 108.8 . . ?
N2 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
O3 C17 C18 110.8(2) . . ?
O3 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 N1 C15 126.62(15) . . ?
C14 N1 HN1 113.9(13) . . ?
C15 N1 HN1 119.2(13) . . ?
C14 N2 C13 122.27(15) . . ?
C14 N2 C16 115.63(15) . . ?
C13 N2 C16 122.10(13) . . ?
C16 O3 C17 114.16(15) . . ?
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
C1 C6 1.379(2) . ?
C1 C2 1.383(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.366(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.529(2) . ?
C7 C13 1.519(2) . ?
C7 C8 1.541(2) . ?
C7 H7 0.9800 . ?
C8 C9 1.507(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10A 1.530(4) . ?
C9 C10B 1.562(10) . ?
C9 H9A 0.979(2) . ?
C9 H9B 0.979(2) . ?
C9 H9C 0.971(2) . ?
C9 H9D 0.984(2) . ?
C10A C10B 1.019(9) . ?
C10A C11B 1.270(11) . ?
C10A C11A 1.522(5) . ?
C10A H9C 1.561(3) . ?
C10A H10A 0.969(3) . ?
C10A H10B 0.978(3) . ?
C10A H10D 1.414(3) . ?
C10A H11C 1.253(3) . ?
C10B C11A 1.205(9) . ?
C10B C11B 1.487(17) . ?
C10B H10A 1.444(9) . ?
C10B H10C 0.981(10) . ?
C10B H10D 0.977(8) . ?
C10B H11B 1.212(9) . ?
C11A C11B 0.720(10) . ?
C11A C12 1.536(4) . ?
C11A H10C 1.428(4) . ?
C11A H11A 0.972(3) . ?
C11A H11B 0.980(4) . ?
C11A H11D 1.169(4) . ?
C11B C12 1.518(10) . ?
C11B H10B 1.477(11) . ?
C11B H11A 1.183(11) . ?
C11B H11C 0.971(12) . ?
C11B H11D 0.974(10) . ?
C12 C13 1.357(2) . ?
C12 C15 1.460(2) . ?
C13 N2 1.405(2) . ?
C14 O2 1.224(2) . ?
C14 N1 1.358(2) . ?
C14 N2 1.375(2) . ?
C15 O1 1.220(2) . ?
C15 N1 1.373(3) . ?
C16 O3 1.391(2) . ?
C16 N2 1.473(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O3 1.439(3) . ?
C17 C18 1.450(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 HN1 0.89(2) . ?
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 HN1 O2 0.89(2) 1.95(2) 2.833(2) 170.4(19) 2_655
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
C6 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
C2 C1 C6 C7 178.73(18) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C4 C5 C6 C7 -178.82(17) . . . . ?
C1 C6 C7 C13 16.0(2) . . . . ?
C5 C6 C7 C13 -164.29(15) . . . . ?
C1 C6 C7 C8 -115.69(19) . . . . ?
C5 C6 C7 C8 64.0(2) . . . . ?
C13 C7 C8 C9 -78.9(2) . . . . ?
C6 C7 C8 C9 52.6(2) . . . . ?
C7 C8 C9 C10A 43.9(3) . . . . ?
C7 C8 C9 C10B 82.3(4) . . . . ?
C8 C9 C10A C10B 76.9(5) . . . . ?
C8 C9 C10A C11B 14.9(9) . . . . ?
C10B C9 C10A C11B -62.0(10) . . . . ?
C8 C9 C10A C11A 41.4(3) . . . . ?
C10B C9 C10A C11A -35.5(5) . . . . ?
C11B C10A C10B C11A -2.0(6) . . . . ?
C9 C10A C10B C11A -136.8(5) . . . . ?
C11A C10A C10B C11B 2.0(6) . . . . ?
C9 C10A C10B C11B -134.8(5) . . . . ?
C11B C10A C10B C9 134.8(5) . . . . ?
C11A C10A C10B C9 136.8(5) . . . . ?
C8 C9 C10B C10A -116.4(4) . . . . ?
C8 C9 C10B C11A -52.0(11) . . . . ?
C10A C9 C10B C11A 64.5(10) . . . . ?
C8 C9 C10B C11B -76.6(7) . . . . ?
C10A C9 C10B C11B 39.8(6) . . . . ?
C10A C10B C11A C11B 3.5(11) . . . . ?
C9 C10B C11A C11B -54.1(14) . . . . ?
C11B C10B C11A C10A -3.5(11) . . . . ?
C9 C10B C11A C10A -57.7(9) . . . . ?
C10A C10B C11A C12 80.4(8) . . . . ?
C11B C10B C11A C12 76.9(11) . . . . ?
C9 C10B C11A C12 22.8(15) . . . . ?
C10B C10A C11A C11B -175.8(13) . . . . ?
C9 C10A C11A C11B -131.3(11) . . . . ?
C11B C10A C11A C10B 175.8(13) . . . . ?
C9 C10A C11A C10B 44.5(6) . . . . ?
C10B C10A C11A C12 -126.1(7) . . . . ?
C11B C10A C11A C12 49.7(10) . . . . ?
C9 C10A C11A C12 -81.6(4) . . . . ?
C10B C11A C11B C10A -2.8(9) . . . . ?
C12 C11A C11B C10A -134.0(7) . . . . ?
C10A C11A C11B C10B 2.8(9) . . . . ?
C12 C11A C11B C10B -131.1(5) . . . . ?
C10B C11A C11B C12 131.1(5) . . . . ?
C10A C11A C11B C12 134.0(7) . . . . ?
C10B C10A C11B C11A 3.4(10) . . . . ?
C9 C10A C11B C11A 62.1(13) . . . . ?
C11A C10A C11B C10B -3.4(10) . . . . ?
C9 C10A C11B C10B 58.7(8) . . . . ?
C10B C10A C11B C12 -75.2(14) . . . . ?
C11A C10A C11B C12 -78.5(14) . . . . ?
C9 C10A C11B C12 -16.5(19) . . . . ?
C10A C10B C11B C11A -175.8(13) . . . . ?
C9 C10B C11B C11A 138.9(10) . . . . ?
C11A C10B C11B C10A 175.8(13) . . . . ?
C9 C10B C11B C10A -45.3(6) . . . . ?
C10A C10B C11B C12 131.1(9) . . . . ?
C11A C10B C11B C12 -53.1(8) . . . . ?
C9 C10B C11B C12 85.9(10) . . . . ?
C11A C11B C12 C13 -116.5(9) . . . . ?
C10A C11B C12 C13 -30.3(17) . . . . ?
C10B C11B C12 C13 -75.4(10) . . . . ?
C11A C11B C12 C15 88.3(10) . . . . ?
C10A C11B C12 C15 174.4(12) . . . . ?
C10B C11B C12 C15 129.3(7) . . . . ?
C10A C11B C12 C11A 86.2(17) . . . . ?
C10B C11B C12 C11A 41.0(9) . . . . ?
C11B C11A C12 C13 81.0(10) . . . . ?
C10B C11A C12 C13 -6.3(10) . . . . ?
C10A C11A C12 C13 40.0(4) . . . . ?
C11B C11A C12 C15 -104.7(10) . . . . ?
C10B C11A C12 C15 168.1(8) . . . . ?
C10A C11A C12 C15 -145.6(3) . . . . ?
C10B C11A C12 C11B -87.3(13) . . . . ?
C10A C11A C12 C11B -41.0(9) . . . . ?
C15 C12 C13 N2 1.6(2) . . . . ?
C11B C12 C13 N2 -153.2(6) . . . . ?
C11A C12 C13 N2 175.7(2) . . . . ?
C15 C12 C13 C7 -177.61(15) . . . . ?
C11B C12 C13 C7 27.6(6) . . . . ?
C11A C12 C13 C7 -3.6(3) . . . . ?
C6 C7 C13 C12 -98.90(19) . . . . ?
C8 C7 C13 C12 32.1(2) . . . . ?
C6 C7 C13 N2 81.84(17) . . . . ?
C8 C7 C13 N2 -147.17(14) . . . . ?
C13 C12 C15 O1 178.76(18) . . . . ?
C11B C12 C15 O1 -26.0(6) . . . . ?
C11A C12 C15 O1 3.9(3) . . . . ?
C13 C12 C15 N1 -1.5(2) . . . . ?
C11B C12 C15 N1 153.8(6) . . . . ?
C11A C12 C15 N1 -176.3(2) . . . . ?
O2 C14 N1 C15 177.06(17) . . . . ?
N2 C14 N1 C15 -2.7(3) . . . . ?
O1 C15 N1 C14 -178.10(18) . . . . ?
C12 C15 N1 C14 2.1(3) . . . . ?
O2 C14 N2 C13 -177.10(16) . . . . ?
N1 C14 N2 C13 2.6(2) . . . . ?
O2 C14 N2 C16 2.1(2) . . . . ?
N1 C14 N2 C16 -178.14(14) . . . . ?
C12 C13 N2 C14 -2.3(2) . . . . ?
C7 C13 N2 C14 177.03(14) . . . . ?
C12 C13 N2 C16 178.55(16) . . . . ?
C7 C13 N2 C16 -2.2(2) . . . . ?
O3 C16 N2 C14 -102.05(17) . . . . ?
O3 C16 N2 C13 77.18(19) . . . . ?
N2 C16 O3 C17 74.4(2) . . . . ?
C18 C17 O3 C16 174.4(2) . . . . ?
