#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/77/2227766.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_2227766
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Quah, Ching Kheng'
'Chandrakantha, B.'
'Isloor, Arun M.'
'Shetty, Prakash'
_publ_section_title
;
 Ethyl 1,5-diphenyl-1H-pyrazole-4-carboxylate
;
_journal_coeditor_code           LH5108
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2282
_journal_page_last               o2283
_journal_paper_doi               10.1107/S1600536810031223
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H16 N2 O2'
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33
_chemical_name_systematic
;
Ethyl 1,5-diphenyl-1H-pyrazole-4-carboxylate
;
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.515(2)
_cell_angle_beta                 104.605(2)
_cell_angle_gamma                104.578(2)
_cell_formula_units_Z            4
_cell_length_a                   9.2015(8)
_cell_length_b                   10.4638(9)
_cell_length_c                   16.9332(15)
_cell_measurement_reflns_used    9846
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.85
_cell_measurement_theta_min      2.54
_cell_volume                     1493.7(2)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type
;
Bruker SMART APEXII DUO CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and 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  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            35429
_diffrn_reflns_theta_full        32.06
_diffrn_reflns_theta_max         32.06
_diffrn_reflns_theta_min         2.06
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_correction_T_min  0.9799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.206
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         10300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0464
_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)+(0.0568P)²+0.3537P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1277
_reflns_number_gt                7846
_reflns_number_total             10300
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5108.cif
_cod_data_source_block           I
_cod_database_code               2227766
_cod_database_fobs_code          2227766
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1A 0.35565(9) 0.55673(8) 0.40840(5) 0.02192(16) Uani d . 1 . .
O O2A 0.10538(10) 0.56385(8) 0.36818(6) 0.02587(18) Uani d . 1 . .
N N1A 0.45702(10) 0.94866(9) 0.36135(5) 0.01681(16) Uani d . 1 . .
N N2A 0.30699(11) 0.95931(9) 0.34270(6) 0.01975(17) Uani d . 1 . .
C C1A 0.59279(14) 1.18876(11) 0.40504(7) 0.0206(2) Uani d . 1 . .
H H1AA 0.5214 1.1983 0.4340 0.025 Uiso calc R 1 . .
C C2A 0.71181(15) 1.30011(11) 0.40425(7) 0.0244(2) Uani d . 1 . .
H H2AA 0.7195 1.3851 0.4325 0.029 Uiso calc R 1 . .
C C3A 0.81991(14) 1.28608(12) 0.36156(7) 0.0241(2) Uani d . 1 . .
H H3AA 0.9000 1.3611 0.3619 0.029 Uiso calc R 1 . .
C C4A 0.80757(13) 1.15950(12) 0.31842(7) 0.0236(2) Uani d . 1 . .
H H4AA 0.8794 1.1499 0.2897 0.028 Uiso calc R 1 . .
C C5A 0.68803(13) 1.04687(11) 0.31798(7) 0.0205(2) Uani d . 1 . .
H H5AA 0.6790 0.9621 0.2888 0.025 Uiso calc R 1 . .
C C6A 0.58225(12) 1.06269(10) 0.36174(6) 0.01680(18) Uani d . 1 . .
C C7A 0.21906(13) 0.83992(11) 0.34605(7) 0.01922(19) Uani d . 1 . .
H H7AA 0.1106 0.8170 0.3360 0.023 Uiso calc R 1 . .
C C8A 0.30951(12) 0.75140(10) 0.36682(6) 0.01709(18) Uani d . 1 . .
C C9A 0.46399(12) 0.82515(10) 0.37630(6) 0.01586(18) Uani d . 1 . .
C C10A 0.61394(12) 0.79251(10) 0.39942(6) 0.01714(18) Uani d . 1 . .
C C11A 0.73369(13) 0.86837(11) 0.47083(7) 0.0213(2) Uani d . 1 . .
H H11A 0.7182 0.9383 0.5044 0.026 Uiso calc R 1 . .
C C12A 0.87630(14) 0.83944(13) 0.49183(8) 0.0270(2) Uani d . 1 . .
H H12A 0.9554 0.8892 0.5400 0.032 Uiso calc R 1 . .
C C13A 0.90112(15) 0.73682(14) 0.44132(8) 0.0299(3) Uani d . 1 . .
H H13A 0.9971 0.7185 0.4553 0.036 Uiso calc R 1 . .
C C14A 0.78255(16) 0.66135(13) 0.36982(8) 0.0287(3) Uani d . 1 . .
H H14A 0.7996 0.5929 0.3357 0.034 Uiso calc R 1 . .
C C15A 0.63871(14) 0.68781(11) 0.34916(7) 0.0223(2) Uani d . 1 . .
H H15A 0.5588 0.6359 0.3019 0.027 Uiso calc R 1 . .
C C16A 0.24476(12) 0.61555(10) 0.38013(6) 0.01793(19) Uani d . 1 . .
C C17A 0.29923(14) 0.41764(11) 0.41795(7) 0.0229(2) Uani d . 1 . .
H H17A 0.2071 0.4069 0.4374 0.027 Uiso calc R 1 . .
H H17B 0.3801 0.3979 0.4594 0.027 Uiso calc R 1 . .
C C18A 0.25821(16) 0.32054(13) 0.33655(8) 0.0295(3) Uani d . 1 . .
H H18A 0.2355 0.2298 0.3456 0.044 Uiso calc R 1 . .
H H18B 0.3453 0.3387 0.3139 0.044 Uiso calc R 1 . .
H H18C 0.1676 0.3309 0.2981 0.044 Uiso calc R 1 . .
O O1B -0.03838(10) 0.61507(8) 0.09374(5) 0.02177(16) Uani d . 1 . .
O O2B -0.23012(11) 0.65343(9) 0.14598(6) 0.0317(2) Uani d . 1 . .
N N1B 0.11226(10) 1.04064(9) 0.13619(5) 0.01698(16) Uani d . 1 . .
N N2B -0.01563(11) 1.06169(9) 0.15725(6) 0.02083(18) Uani d . 1 . .
C C1B 0.18999(13) 1.25412(11) 0.09434(7) 0.0210(2) Uani d . 1 . .
H H1BA 0.0849 1.2424 0.0668 0.025 Uiso calc R 1 . .
C C2B 0.30546(15) 1.37023(12) 0.09588(8) 0.0253(2) Uani d . 1 . .
H H2BA 0.2772 1.4370 0.0698 0.030 Uiso calc R 1 . .
C C3B 0.46273(14) 1.38736(12) 0.13605(7) 0.0248(2) Uani d . 1 . .
H H3BA 0.5396 1.4651 0.1369 0.030 Uiso calc R 1 . .
C C4B 0.50423(13) 1.28742(12) 0.17498(7) 0.0234(2) Uani d . 1 . .
H H4BA 0.6095 1.2980 0.2013 0.028 Uiso calc R 1 . .
C C5B 0.38976(13) 1.17171(11) 0.17499(7) 0.0202(2) Uani d . 1 . .
H H5BA 0.4178 1.1056 0.2019 0.024 Uiso calc R 1 . .
C C6B 0.23336(12) 1.15597(10) 0.13444(6) 0.01708(18) Uani d . 1 . .
C C7B -0.10204(13) 0.93979(11) 0.15709(7) 0.0208(2) Uani d . 1 . .
H H7BA -0.1970 0.9225 0.1696 0.025 Uiso calc R 1 . .
C C8B -0.03368(12) 0.83895(10) 0.13579(6) 0.01782(19) Uani d . 1 . .
C C9B 0.10638(12) 0.90767(10) 0.12275(6) 0.01598(18) Uani d . 1 . .
C C10B 0.22948(12) 0.86100(10) 0.09737(6) 0.01613(18) Uani d . 1 . .
C C11B 0.26595(13) 0.89043(11) 0.02510(7) 0.0201(2) Uani d . 1 . .
H H11B 0.2110 0.9379 -0.0075 0.024 Uiso calc R 1 . .
C C12B 0.38418(14) 0.84894(12) 0.00174(7) 0.0251(2) Uani d . 1 . .
H H12B 0.4064 0.8671 -0.0470 0.030 Uiso calc R 1 . .
C C13B 0.46887(14) 0.78059(12) 0.05093(8) 0.0268(2) Uani d . 1 . .
H H13B 0.5492 0.7544 0.0358 0.032 Uiso calc R 1 . .
C C14B 0.43344(14) 0.75128(12) 0.12286(8) 0.0245(2) Uani d . 1 . .
H H14B 0.4903 0.7055 0.1559 0.029 Uiso calc R 1 . .
C C15B 0.31331(13) 0.79004(11) 0.14585(7) 0.0199(2) Uani d . 1 . .
H H15B 0.2889 0.7687 0.1935 0.024 Uiso calc R 1 . .
C C16B -0.11071(13) 0.69496(11) 0.12682(7) 0.0197(2) Uani d . 1 . .
C C17B -0.10723(15) 0.47049(11) 0.08556(7) 0.0235(2) Uani d . 1 . .
H H17C -0.0773 0.4212 0.0428 0.028 Uiso calc R 1 . .
H H17E -0.2210 0.4486 0.0683 0.028 Uiso calc R 1 . .
C C18B -0.05319(17) 0.42793(13) 0.16657(8) 0.0311(3) Uani d . 1 . .
H H18G -0.0918 0.3315 0.1583 0.047 Uiso calc R 1 . .
H H18D -0.0928 0.4690 0.2073 0.047 Uiso calc R 1 . .
H H18E 0.0597 0.4560 0.1859 0.047 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C16A O1A C17A . . 116.10(9) ?
C9A N1A N2A . . 112.87(8) ?
C9A N1A C6A . . 128.77(9) ?
N2A N1A C6A . . 118.36(8) ?
C7A N2A N1A . . 104.39(9) ?
C2A C1A C6A . . 118.80(10) ?
C2A C1A H1AA . . 120.6 ?
C6A C1A H1AA . . 120.6 ?
C1A C2A C3A . . 120.78(10) ?
C1A C2A H2AA . . 119.6 ?
C3A C2A H2AA . . 119.6 ?
C4A C3A C2A . . 119.73(10) ?
C4A C3A H3AA . . 120.1 ?
C2A C3A H3AA . . 120.1 ?
C3A C4A C5A . . 120.24(10) ?
C3A C4A H4AA . . 119.9 ?
C5A C4A H4AA . . 119.9 ?
C6A C5A C4A . . 119.18(10) ?
C6A C5A H5AA . . 120.4 ?
C4A C5A H5AA . . 120.4 ?
C1A C6A C5A . . 121.27(10) ?
C1A C6A N1A . . 118.48(9) ?
C5A C6A N1A . . 120.24(9) ?
N2A C7A C8A . . 111.99(9) ?
N2A C7A H7AA . . 124.0 ?
C8A C7A H7AA . . 124.0 ?
C9A C8A C7A . . 105.26(9) ?
C9A C8A C16A . . 130.70(10) ?
C7A C8A C16A . . 123.90(9) ?
N1A C9A C8A . . 105.49(9) ?
N1A C9A C10A . . 122.05(9) ?
C8A C9A C10A . . 132.43(9) ?
C11A C10A C15A . . 119.52(10) ?
C11A C10A C9A . . 119.93(9) ?
C15A C10A C9A . . 120.52(10) ?
C12A C11A C10A . . 120.01(11) ?
C12A C11A H11A . . 120.0 ?
C10A C11A H11A . . 120.0 ?
C13A C12A C11A . . 120.29(12) ?
C13A C12A H12A . . 119.9 ?
C11A C12A H12A . . 119.9 ?
C12A C13A C14A . . 119.96(11) ?
C12A C13A H13A . . 120.0 ?
C14A C13A H13A . . 120.0 ?
C15A C14A C13A . . 120.17(11) ?
C15A C14A H14A . . 119.9 ?
C13A C14A H14A . . 119.9 ?
C14A C15A C10A . . 120.02(11) ?
C14A C15A H15A . . 120.0 ?
C10A C15A H15A . . 120.0 ?
O2A C16A O1A . . 123.97(10) ?
O2A C16A C8A . . 123.00(10) ?
O1A C16A C8A . . 113.02(9) ?
O1A C17A C18A . . 110.68(9) ?
O1A C17A H17A . . 109.5 ?
C18A C17A H17A . . 109.5 ?
O1A C17A H17B . . 109.5 ?
C18A C17A H17B . . 109.5 ?
H17A C17A H17B . . 108.1 ?
C17A C18A H18A . . 109.5 ?
C17A C18A H18B . . 109.5 ?
H18A C18A H18B . . 109.5 ?
C17A C18A H18C . . 109.5 ?
H18A C18A H18C . . 109.5 ?
H18B C18A H18C . . 109.5 ?
C16B O1B C17B . . 115.69(8) ?
C9B N1B N2B . . 112.76(8) ?
C9B N1B C6B . . 129.09(9) ?
N2B N1B C6B . . 118.10(8) ?
C7B N2B N1B . . 104.38(8) ?
C6B C1B C2B . . 119.22(10) ?
C6B C1B H1BA . . 120.4 ?
C2B C1B H1BA . . 120.4 ?
C3B C2B C1B . . 120.56(11) ?
C3B C2B H2BA . . 119.7 ?
C1B C2B H2BA . . 119.7 ?
C4B C3B C2B . . 119.46(11) ?
C4B C3B H3BA . . 120.3 ?
C2B C3B H3BA . . 120.3 ?
C3B C4B C5B . . 120.59(11) ?
C3B C4B H4BA . . 119.7 ?
C5B C4B H4BA . . 119.7 ?
C6B C5B C4B . . 119.24(10) ?
C6B C5B H5BA . . 120.4 ?
C4B C5B H5BA . . 120.4 ?
C5B C6B C1B . . 120.92(10) ?
C5B C6B N1B . . 120.56(9) ?
C1B C6B N1B . . 118.47(9) ?
N2B C7B C8B . . 112.23(9) ?
N2B C7B H7BA . . 123.9 ?
C8B C7B H7BA . . 123.9 ?
C9B C8B C7B . . 105.21(9) ?
C9B C8B C16B . . 131.97(9) ?
C7B C8B C16B . . 122.74(9) ?
N1B C9B C8B . . 105.43(9) ?
N1B C9B C10B . . 122.19(9) ?
C8B C9B C10B . . 132.36(9) ?
C15B C10B C11B . . 119.26(9) ?
C15B C10B C9B . . 120.66(9) ?
C11B C10B C9B . . 120.06(9) ?
C12B C11B C10B . . 120.32(11) ?
C12B C11B H11B . . 119.8 ?
C10B C11B H11B . . 119.8 ?
C13B C12B C11B . . 120.14(11) ?
C13B C12B H12B . . 119.9 ?
C11B C12B H12B . . 119.9 ?
C12B C13B C14B . . 119.81(10) ?
C12B C13B H13B . . 120.1 ?
C14B C13B H13B . . 120.1 ?
C13B C14B C15B . . 120.44(11) ?
C13B C14B H14B . . 119.8 ?
C15B C14B H14B . . 119.8 ?
C14B C15B C10B . . 120.00(10) ?
C14B C15B H15B . . 120.0 ?
C10B C15B H15B . . 120.0 ?
O2B C16B O1B . . 124.08(10) ?
O2B C16B C8B . . 122.69(10) ?
O1B C16B C8B . . 113.22(9) ?
O1B C17B C18B . . 111.06(10) ?
O1B C17B H17C . . 109.4 ?
C18B C17B H17C . . 109.4 ?
O1B C17B H17E . . 109.4 ?
C18B C17B H17E . . 109.4 ?
H17C C17B H17E . . 108.0 ?
C17B C18B H18G . . 109.5 ?
C17B C18B H18D . . 109.5 ?
H18G C18B H18D . . 109.5 ?
C17B C18B H18E . . 109.5 ?
H18G C18B H18E . . 109.5 ?
H18D C18B H18E . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1A C16A . 1.3402(13) ?
O1A C17A . 1.4620(13) ?
O2A C16A . 1.2123(13) ?
N1A C9A . 1.3630(13) ?
N1A N2A . 1.3728(12) ?
N1A C6A . 1.4330(13) ?
N2A C7A . 1.3235(14) ?
C1A C2A . 1.3879(15) ?
C1A C6A . 1.3906(14) ?
C1A H1AA . 0.9300 ?
C2A C3A . 1.3935(17) ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.3893(17) ?
C3A H3AA . 0.9300 ?
C4A C5A . 1.3927(15) ?
C4A H4AA . 0.9300 ?
C5A C6A . 1.3917(14) ?
C5A H5AA . 0.9300 ?
C7A C8A . 1.4142(15) ?
C7A H7AA . 0.9300 ?
C8A C9A . 1.3936(14) ?
C8A C16A . 1.4668(14) ?
C9A C10A . 1.4743(15) ?
C10A C11A . 1.3940(15) ?
C10A C15A . 1.3986(14) ?
C11A C12A . 1.3903(16) ?
C11A H11A . 0.9300 ?
C12A C13A . 1.3851(19) ?
C12A H12A . 0.9300 ?
C13A C14A . 1.389(2) ?
C13A H13A . 0.9300 ?
C14A C15A . 1.3882(17) ?
C14A H14A . 0.9300 ?
C15A H15A . 0.9300 ?
C17A C18A . 1.5010(16) ?
C17A H17A . 0.9700 ?
C17A H17B . 0.9700 ?
C18A H18A . 0.9600 ?
C18A H18B . 0.9600 ?
C18A H18C . 0.9600 ?
O1B C16B . 1.3420(13) ?
O1B C17B . 1.4587(13) ?
O2B C16B . 1.2156(13) ?
N1B C9B . 1.3651(13) ?
N1B N2B . 1.3719(12) ?
N1B C6B . 1.4311(13) ?
N2B C7B . 1.3216(14) ?
C1B C6B . 1.3882(15) ?
C1B C2B . 1.3905(16) ?
C1B H1BA . 0.9300 ?
C2B C3B . 1.3893(18) ?
C2B H2BA . 0.9300 ?
C3B C4B . 1.3887(18) ?
C3B H3BA . 0.9300 ?
C4B C5B . 1.3905(15) ?
C4B H4BA . 0.9300 ?
C5B C6B . 1.3865(15) ?
C5B H5BA . 0.9300 ?
C7B C8B . 1.4100(14) ?
C7B H7BA . 0.9300 ?
C8B C9B . 1.3947(14) ?
C8B C16B . 1.4643(14) ?
C9B C10B . 1.4749(14) ?
C10B C15B . 1.3959(15) ?
C10B C11B . 1.3996(14) ?
C11B C12B . 1.3922(15) ?
C11B H11B . 0.9300 ?
C12B C13B . 1.3862(19) ?
C12B H12B . 0.9300 ?
C13B C14B . 1.3898(18) ?
C13B H13B . 0.9300 ?
C14B C15B . 1.3926(15) ?
C14B H14B . 0.9300 ?
C15B H15B . 0.9300 ?
C17B C18B . 1.5015(17) ?
C17B H17C . 0.9700 ?
C17B H17E . 0.9700 ?
C18B H18G . 0.9600 ?
C18B H18D . 0.9600 ?
C18B H18E . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C3A H3AA O2A 1_665 0.93 2.43 3.3591(16) 177 yes
C3B H3BA O2B 1_665 0.93 2.46 3.3829(16) 172 yes
C13A H13A O2A 1_655 0.93 2.59 3.2622(17) 129 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9A N1A N2A C7A . . . . -0.07(11) ?
C6A N1A N2A C7A . . . . 179.13(9) ?
C6A C1A C2A C3A . . . . -0.58(17) ?
C1A C2A C3A C4A . . . . 0.76(18) ?
C2A C3A C4A C5A . . . . -0.20(18) ?
C3A C4A C5A C6A . . . . -0.50(17) ?
C2A C1A C6A C5A . . . . -0.14(16) ?
C2A C1A C6A N1A . . . . -178.67(10) ?
C4A C5A C6A C1A . . . . 0.68(16) ?
C4A C5A C6A N1A . . . . 179.18(10) ?
C9A N1A C6A C1A . . . . -132.33(11) ?
N2A N1A C6A C1A . . . . 48.61(13) ?
C9A N1A C6A C5A . . . . 49.12(15) ?
N2A N1A C6A C5A . . . . -129.93(11) ?
N1A N2A C7A C8A . . . . 0.13(11) ?
N2A C7A C8A C9A . . . . -0.14(12) ?
N2A C7A C8A C16A . . . . 175.97(9) ?
N2A N1A C9A C8A . . . . -0.01(11) ?
C6A N1A C9A C8A . . . . -179.11(9) ?
N2A N1A C9A C10A . . . . -178.57(9) ?
C6A N1A C9A C10A . . . . 2.33(15) ?
C7A C8A C9A N1A . . . . 0.09(11) ?
C16A C8A C9A N1A . . . . -175.66(10) ?
C7A C8A C9A C10A . . . . 178.43(10) ?
C16A C8A C9A C10A . . . . 2.68(19) ?
N1A C9A C10A C11A . . . . 59.02(14) ?
C8A C9A C10A C11A . . . . -119.10(13) ?
N1A C9A C10A C15A . . . . -119.47(11) ?
C8A C9A C10A C15A . . . . 62.42(15) ?
C15A C10A C11A C12A . . . . -0.23(16) ?
C9A C10A C11A C12A . . . . -178.73(10) ?
C10A C11A C12A C13A . . . . 1.08(17) ?
C11A C12A C13A C14A . . . . -0.71(18) ?
C12A C13A C14A C15A . . . . -0.50(18) ?
C13A C14A C15A C10A . . . . 1.35(18) ?
C11A C10A C15A C14A . . . . -0.98(16) ?
C9A C10A C15A C14A . . . . 177.51(10) ?
C17A O1A C16A O2A . . . . 5.26(15) ?
C17A O1A C16A C8A . . . . -176.13(8) ?
C9A C8A C16A O2A . . . . -179.16(11) ?
C7A C8A C16A O2A . . . . 5.79(16) ?
C9A C8A C16A O1A . . . . 2.22(15) ?
C7A C8A C16A O1A . . . . -172.83(9) ?
C16A O1A C17A C18A . . . . 83.99(12) ?
C9B N1B N2B C7B . . . . 0.18(12) ?
C6B N1B N2B C7B . . . . -177.38(9) ?
C6B C1B C2B C3B . . . . 0.86(17) ?
C1B C2B C3B C4B . . . . -0.09(17) ?
C2B C3B C4B C5B . . . . -0.87(17) ?
C3B C4B C5B C6B . . . . 1.04(16) ?
C4B C5B C6B C1B . . . . -0.24(15) ?
C4B C5B C6B N1B . . . . -177.47(9) ?
C2B C1B C6B C5B . . . . -0.70(16) ?
C2B C1B C6B N1B . . . . 176.58(10) ?
C9B N1B C6B C5B . . . . -46.46(15) ?
N2B N1B C6B C5B . . . . 130.65(10) ?
C9B N1B C6B C1B . . . . 136.25(11) ?
N2B N1B C6B C1B . . . . -46.64(13) ?
N1B N2B C7B C8B . . . . -0.39(12) ?
N2B C7B C8B C9B . . . . 0.45(13) ?
N2B C7B C8B C16B . . . . -176.57(10) ?
N2B N1B C9B C8B . . . . 0.09(12) ?
C6B N1B C9B C8B . . . . 177.32(10) ?
N2B N1B C9B C10B . . . . 178.45(9) ?
C6B N1B C9B C10B . . . . -4.31(16) ?
C7B C8B C9B N1B . . . . -0.30(11) ?
C16B C8B C9B N1B . . . . 176.32(11) ?
C7B C8B C9B C10B . . . . -178.43(11) ?
C16B C8B C9B C10B . . . . -1.8(2) ?
N1B C9B C10B C15B . . . . 121.72(11) ?
C8B C9B C10B C15B . . . . -60.41(16) ?
N1B C9B C10B C11B . . . . -56.76(14) ?
C8B C9B C10B C11B . . . . 121.11(13) ?
C15B C10B C11B C12B . . . . 0.22(16) ?
C9B C10B C11B C12B . . . . 178.72(10) ?
C10B C11B C12B C13B . . . . -1.36(17) ?
C11B C12B C13B C14B . . . . 1.23(17) ?
C12B C13B C14B C15B . . . . 0.04(17) ?
C13B C14B C15B C10B . . . . -1.18(17) ?
C11B C10B C15B C14B . . . . 1.04(16) ?
C9B C10B C15B C14B . . . . -177.45(10) ?
C17B O1B C16B O2B . . . . -3.28(16) ?
C17B O1B C16B C8B . . . . 178.27(9) ?
C9B C8B C16B O2B . . . . 175.52(12) ?
C7B C8B C16B O2B . . . . -8.35(18) ?
C9B C8B C16B O1B . . . . -6.00(17) ?
C7B C8B C16B O1B . . . . 170.12(10) ?
C16B O1B C17B C18B . . . . -81.78(13) ?
