#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/06/2220689.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2220689
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Kia, Reza'
'Vijesh, A. M.'
'Isloor, Arun M.'
_publ_section_title
;
 5-Diethylamino-2-[(E)-(4-methyl-3-nitrophenyl)iminomethyl]phenol:
 a redetermination
;
_journal_coeditor_code           AT2709
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o349
_journal_page_last               o350
_journal_paper_doi               10.1107/S1600536809001731
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H21 N3 O3'
_chemical_formula_moiety         'C18 H21 N3 O3'
_chemical_formula_sum            'C18 H21 N3 O3'
_chemical_formula_weight         327.38
_chemical_melting_point          405
_chemical_name_systematic
;
5-Diethylamino-2-[(E)-(4-methyl-3-nitrophenyl)iminomethyl]phenol
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.7130(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.27770(10)
_cell_length_b                   22.1792(5)
_cell_length_c                   10.3473(2)
_cell_measurement_reflns_used    4554
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      29.77
_cell_measurement_theta_min      2.73
_cell_volume                     1622.59(5)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21678
_diffrn_reflns_theta_full        30.10
_diffrn_reflns_theta_max         30.10
_diffrn_reflns_theta_min         2.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9967
_exptl_absorpt_correction_T_min  0.9560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.221
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         4744
_refine_ls_number_restraints     1197
_refine_ls_restrained_S_all      0.922
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0430
_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)+(0.0561P)²+0.1724P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1174
_reflns_number_gt                3239
_reflns_number_total             4744
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2709.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2220689
_cod_database_fobs_code          2220689
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.3739(19) 0.0973(10) 1.0926(17) 0.0234(9) Uani d PDU 0.567(4) A 1
H H1A 0.3089 0.0791 1.0262 0.035 Uiso calc PR 0.567(4) A 1
C C1A 0.5374(9) 0.1157(3) 1.0663(5) 0.0125(7) Uani d PDU 0.567(4) A 1
C C2A 0.647(2) 0.1575(12) 1.1497(19) 0.0255(9) Uani d PDU 0.567(4) A 1
H H2AA 0.6140 0.1682 1.2301 0.031 Uiso calc PR 0.567(4) A 1
C C3A 0.8077(5) 0.18510(16) 1.1189(3) 0.0255(6) Uani d PDU 0.567(4) A 1
C C4A 0.8620(5) 0.16478(18) 1.0018(4) 0.0296(7) Uani d PDU 0.567(4) A 1
H H4AA 0.9726 0.1803 0.9803 0.035 Uiso calc PR 0.567(4) A 1
C C5A 0.7531(7) 0.1227(3) 0.9210(6) 0.0252(10) Uani d PDU 0.567(4) A 1
H H5AA 0.7911 0.1099 0.8436 0.030 Uiso calc PR 0.567(4) A 1
C C6A 0.5879(14) 0.0974(8) 0.9470(12) 0.0197(10) Uani d PDU 0.567(4) A 1
C C7A 0.4817(12) 0.0550(5) 0.8538(8) 0.0179(13) Uani d PDU 0.567(4) A 1
H H7AA 0.5300 0.0422 0.7807 0.021 Uiso calc PR 0.567(4) A 1
N N1A 0.3211(11) 0.0336(5) 0.8673(8) 0.0179(9) Uani d PDU 0.567(4) A 1
C C8A 0.2039(12) -0.0048(5) 0.7729(8) 0.0250(14) Uani d PDU 0.567(4) A 1
C C9A 0.2462(14) -0.0271(7) 0.6580(10) 0.0230(14) Uani d PDU 0.567(4) A 1
H H9AA 0.3631 -0.0171 0.6376 0.028 Uiso calc PR 0.567(4) A 1
C C10A 0.1184(11) -0.0637(5) 0.5730(8) 0.0221(11) Uani d PDU 0.567(4) A 1
C C11A -0.0553(11) -0.0821(6) 0.5965(9) 0.0226(11) Uani d PDU 0.567(4) A 1
C C12A -0.0955(14) -0.0564(5) 0.7096(9) 0.0309(12) Uani d PDU 0.567(4) A 1
H H12A -0.2169 -0.0637 0.7256 0.037 Uiso calc PR 0.567(4) A 1
C C13A 0.0291(11) -0.0210(5) 0.8002(9) 0.0264(12) Uani d PDU 0.567(4) A 1
H H13A -0.0024 -0.0078 0.8796 0.032 Uiso calc PR 0.567(4) A 1
N N2A 0.9119(3) 0.22760(14) 1.1993(3) 0.0402(7) Uani d PDU 0.567(4) A 1
C C14A 1.1461(3) 0.22808(9) 1.21715(19) 0.0262(5) Uani d PDU 0.567(4) A 1
H H14A 1.2168 0.2369 1.3093 0.031 Uiso calc PR 0.567(4) A 1
H H14B 1.1942 0.1908 1.1843 0.031 Uiso calc PR 0.567(4) A 1
C C15A 1.1392(3) 0.28153(10) 1.1233(2) 0.0327(6) Uani d PDU 0.567(4) A 1
H H15A 1.2677 0.2912 1.1158 0.049 Uiso calc PR 0.567(4) A 1
H H15B 1.0847 0.3165 1.1585 0.049 Uiso calc PR 0.567(4) A 1
H H15C 1.0609 0.2712 1.0353 0.049 Uiso calc PR 0.567(4) A 1
C C16A 0.8713(9) 0.2448(3) 1.3260(6) 0.0268(11) Uani d PDU 0.567(4) A 1
H H16A 0.9900 0.2580 1.3881 0.032 Uiso calc PR 0.567(4) A 1
H H16B 0.8232 0.2092 1.3655 0.032 Uiso calc PR 0.567(4) A 1
C C17A 0.7284(9) 0.2947(3) 1.3107(9) 0.0343(11) Uani d PDU 0.567(4) A 1
H H17A 0.7058 0.3047 1.3979 0.052 Uiso calc PR 0.567(4) A 1
H H17B 0.6097 0.2816 1.2509 0.052 Uiso calc PR 0.567(4) A 1
H H17C 0.7764 0.3304 1.2734 0.052 Uiso calc PR 0.567(4) A 1
C C18A -0.1980(12) -0.1223(4) 0.5104(10) 0.0286(13) Uani d PDU 0.567(4) A 1
H H18A -0.3071 -0.1270 0.5498 0.043 Uiso calc PR 0.567(4) A 1
H H18B -0.1412 -0.1619 0.5034 0.043 Uiso calc PR 0.567(4) A 1
H H18C -0.2394 -0.1045 0.4216 0.043 Uiso calc PR 0.567(4) A 1
N N3A 0.184(3) -0.0827(19) 0.455(2) 0.0313(14) Uani d PDU 0.567(4) A 1
O O2A 0.3440(11) -0.0694(3) 0.4470(8) 0.0529(17) Uani d PDU 0.567(4) A 1
O O3A 0.0868(6) -0.1188(2) 0.3802(5) 0.0700(13) Uani d PDU 0.567(4) A 1
O O1B 0.398(3) 0.0963(13) 1.092(2) 0.0234(9) Uani d PDU 0.433(4) A 2
H H1B 0.3551 0.0680 1.0391 0.035 Uiso calc PR 0.433(4) A 2
C C1B 0.5589(14) 0.1191(5) 1.0618(9) 0.0306(17) Uani d PDU 0.433(4) A 2
C C2B 0.665(3) 0.1575(15) 1.155(2) 0.0255(9) Uani d PDU 0.433(4) A 2
H H2BA 0.6148 0.1741 1.2235 0.031 Uiso calc PR 0.433(4) A 2
C C3B 0.8515(5) 0.17175(19) 1.1452(4) 0.0181(7) Uani d PDU 0.433(4) A 2
C C4B 0.9079(6) 0.1517(2) 1.0301(4) 0.0218(8) Uani d PDU 0.433(4) A 2
H H4BA 1.0277 0.1636 1.0172 0.026 Uiso calc PR 0.433(4) A 2
C C5B 0.7946(8) 0.1158(4) 0.9378(8) 0.0221(11) Uani d PDU 0.433(4) A 2
H H5BA 0.8374 0.1034 0.8620 0.027 Uiso calc PR 0.433(4) A 2
C C6B 0.6180(19) 0.0966(10) 0.9512(17) 0.0197(10) Uani d PDU 0.433(4) A 2
C C7B 0.4953(17) 0.0590(7) 0.8598(12) 0.030(2) Uani d PDU 0.433(4) A 2
H H7BA 0.5334 0.0463 0.7824 0.036 Uiso calc PR 0.433(4) A 2
N N1B 0.3323(17) 0.0409(7) 0.8762(12) 0.0250(18) Uani d PDU 0.433(4) A 2
C C8B 0.2194(14) 0.0014(6) 0.7836(10) 0.0169(13) Uani d PDU 0.433(4) A 2
C C9B 0.2642(19) -0.0211(9) 0.6684(14) 0.0189(13) Uani d PDU 0.433(4) A 2
H H9BA 0.3822 -0.0117 0.6491 0.023 Uiso calc PR 0.433(4) A 2
C C10B 0.1362(14) -0.0571(6) 0.5834(10) 0.0213(14) Uani d PDU 0.433(4) A 2
C C11B -0.0420(16) -0.0732(8) 0.6030(12) 0.028(2) Uani d PDU 0.433(4) A 2
C C12B -0.0749(16) -0.0544(7) 0.7258(11) 0.0330(19) Uani d PDU 0.433(4) A 2
H H12B -0.1823 -0.0688 0.7536 0.040 Uiso calc PR 0.433(4) A 2
C C13B 0.0489(16) -0.0153(7) 0.8050(13) 0.033(2) Uani d PDU 0.433(4) A 2
H H13B 0.0131 0.0013 0.8800 0.040 Uiso calc PR 0.433(4) A 2
N N2B 0.9676(3) 0.20711(11) 1.2388(2) 0.0158(5) Uani d PDU 0.433(4) A 2
C C14B 1.0549(4) 0.26562(12) 1.1520(3) 0.0288(7) Uani d PDU 0.433(4) A 2
H H14C 1.0015 0.2654 1.0547 0.035 Uiso calc PR 0.433(4) A 2
H H14D 1.0482 0.3063 1.1899 0.035 Uiso calc PR 0.433(4) A 2
C C15B 1.2453(4) 0.23619(13) 1.1946(3) 0.0343(8) Uani d PDU 0.433(4) A 2
H H15D 1.3381 0.2593 1.1602 0.051 Uiso calc PR 0.433(4) A 2
H H15E 1.2384 0.1950 1.1595 0.051 Uiso calc PR 0.433(4) A 2
H H15F 1.2839 0.2350 1.2920 0.051 Uiso calc PR 0.433(4) A 2
C C16B 0.9026(12) 0.2355(5) 1.3477(7) 0.0245(12) Uani d PDU 0.433(4) A 2
H H16C 1.0144 0.2490 1.4162 0.029 Uiso calc PR 0.433(4) A 2
H H16D 0.8356 0.2050 1.3891 0.029 Uiso calc PR 0.433(4) A 2
C C17B 0.7722(11) 0.2891(4) 1.3056(11) 0.0315(13) Uani d PDU 0.433(4) A 2
H H17D 0.7339 0.3054 1.3832 0.047 Uiso calc PR 0.433(4) A 2
H H17E 0.6598 0.2761 1.2389 0.047 Uiso calc PR 0.433(4) A 2
H H17F 0.8388 0.3203 1.2674 0.047 Uiso calc PR 0.433(4) A 2
C C18B -0.1932(17) -0.1105(6) 0.5125(13) 0.0300(17) Uani d PDU 0.433(4) A 2
H H18D -0.3026 -0.1143 0.5518 0.045 Uiso calc PR 0.433(4) A 2
H H18E -0.1429 -0.1507 0.5014 0.045 Uiso calc PR 0.433(4) A 2
H H18F -0.2320 -0.0907 0.4256 0.045 Uiso calc PR 0.433(4) A 2
N N3B 0.185(4) -0.078(2) 0.459(3) 0.0313(14) Uani d PDU 0.433(4) A 2
O O2B 0.3391(12) -0.0633(4) 0.4405(10) 0.0260(11) Uani d PDU 0.433(4) A 2
O O3B 0.0621(6) -0.10006(19) 0.3677(5) 0.0255(7) Uani d PDU 0.433(4) A 2
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
O1A C1A C2A . . 119.0(8) ?
O1A C1A C6A . . 120.7(7) ?
C2A C1A C6A . . 120.0(6) ?
C1A C2A C3A . . 122.2(8) ?
C1A C2A H2AA . . 118.9 ?
C3A C2A H2AA . . 118.9 ?
N2A C3A C2A . . 121.9(4) ?
N2A C3A C4A . . 120.6(3) ?
C2A C3A C4A . . 117.4(5) ?
C5A C4A C3A . . 119.6(4) ?
C5A C4A H4AA . . 120.2 ?
C3A C4A H4AA . . 120.2 ?
C4A C5A C6A . . 123.3(5) ?
C4A C5A H5AA . . 118.4 ?
C6A C5A H5AA . . 118.4 ?
C5A C6A C1A . . 117.3(6) ?
C5A C6A C7A . . 118.7(6) ?
C1A C6A C7A . . 124.0(6) ?
N1A C7A C6A . . 121.5(7) ?
N1A C7A H7AA . . 119.3 ?
C6A C7A H7AA . . 119.3 ?
C7A N1A C8A . . 123.7(6) ?
C9A C8A C13A . . 118.3(6) ?
C9A C8A N1A . . 125.7(6) ?
C13A C8A N1A . . 116.0(6) ?
C10A C9A C8A . . 120.1(6) ?
C10A C9A H9AA . . 119.9 ?
C8A C9A H9AA . . 119.9 ?
C9A C10A C11A . . 124.0(6) ?
C9A C10A N3A . . 113.1(6) ?
C11A C10A N3A . . 123.0(6) ?
C12A C11A C10A . . 113.8(6) ?
C12A C11A C18A . . 119.4(6) ?
C10A C11A C18A . . 126.7(6) ?
C13A C12A C11A . . 124.5(7) ?
C13A C12A H12A . . 117.7 ?
C11A C12A H12A . . 117.7 ?
C12A C13A C8A . . 119.1(6) ?
C12A C13A H13A . . 120.5 ?
C8A C13A H13A . . 120.5 ?
C3A N2A C16A . . 121.8(4) ?
C3A N2A C14A . . 118.5(2) ?
C16A N2A C14A . . 108.5(3) ?
C15A C14A N2A . . 93.22(16) ?
C15A C14A H14A . . 113.1 ?
N2A C14A H14A . . 113.1 ?
C15A C14A H14B . . 113.1 ?
N2A C14A H14B . . 113.1 ?
H14A C14A H14B . . 110.5 ?
C14A C15A H15A . . 109.5 ?
C14A C15A H15B . . 109.5 ?
H15A C15A H15B . . 109.5 ?
C14A C15A H15C . . 109.5 ?
H15A C15A H15C . . 109.5 ?
H15B C15A H15C . . 109.5 ?
N2A C16A C17A . . 112.4(4) ?
N2A C16A H16A . . 109.1 ?
C17A C16A H16A . . 109.1 ?
N2A C16A H16B . . 109.1 ?
C17A C16A H16B . . 109.1 ?
H16A C16A H16B . . 107.9 ?
C16A C17A H17A . . 109.5 ?
C16A C17A H17B . . 109.5 ?
H17A C17A H17B . . 109.5 ?
C16A C17A H17C . . 109.5 ?
H17A C17A H17C . . 109.5 ?
H17B C17A H17C . . 109.5 ?
C11A C18A H18A . . 109.5 ?
C11A C18A H18B . . 109.5 ?
H18A C18A H18B . . 109.5 ?
C11A C18A H18C . . 109.5 ?
H18A C18A H18C . . 109.5 ?
H18B C18A H18C . . 109.5 ?
O3A N3A O2A . . 122.4(11) ?
O3A N3A C10A . . 117.3(8) ?
O2A N3A C10A . . 119.3(7) ?
C1B O1B H1B . . 109.5 ?
O1B C1B C2B . . 115.9(10) ?
O1B C1B C6B . . 119.6(10) ?
C2B C1B C6B . . 123.9(9) ?
C1B C2B C3B . . 118.5(10) ?
C1B C2B H2BA . . 120.7 ?
C3B C2B H2BA . . 120.7 ?
N2B C3B C2B . . 121.2(6) ?
N2B C3B C4B . . 121.3(4) ?
C2B C3B C4B . . 117.3(6) ?
C5B C4B C3B . . 121.6(5) ?
C5B C4B H4BA . . 119.2 ?
C3B C4B H4BA . . 119.2 ?
C4B C5B C6B . . 122.0(7) ?
C4B C5B H5BA . . 119.0 ?
C6B C5B H5BA . . 119.0 ?
C5B C6B C1B . . 116.1(8) ?
C5B C6B C7B . . 124.6(9) ?
C1B C6B C7B . . 119.2(8) ?
N1B C7B C6B . . 123.2(10) ?
N1B C7B H7BA . . 118.4 ?
C6B C7B H7BA . . 118.4 ?
C7B N1B C8B . . 120.4(9) ?
C13B C8B C9B . . 116.5(8) ?
C13B C8B N1B . . 117.7(8) ?
C9B C8B N1B . . 125.8(8) ?
C10B C9B C8B . . 119.5(9) ?
C10B C9B H9BA . . 120.2 ?
C8B C9B H9BA . . 120.2 ?
C9B C10B C11B . . 124.3(7) ?
C9B C10B N3B . . 117.9(7) ?
C11B C10B N3B . . 117.8(8) ?
C10B C11B C12B . . 114.5(7) ?
C10B C11B C18B . . 127.6(9) ?
C12B C11B C18B . . 117.8(9) ?
C13B C12B C11B . . 119.8(8) ?
C13B C12B H12B . . 120.1 ?
C11B C12B H12B . . 120.1 ?
C8B C13B C12B . . 124.6(9) ?
C8B C13B H13B . . 117.7 ?
C12B C13B H13B . . 117.7 ?
C3B N2B C16B . . 122.2(5) ?
C3B N2B C14B . . 107.1(2) ?
C16B N2B C14B . . 107.1(5) ?
C15B C14B N2B . . 87.1(2) ?
C15B C14B H14C . . 114.1 ?
N2B C14B H14C . . 114.1 ?
C15B C14B H14D . . 114.1 ?
N2B C14B H14D . . 114.1 ?
H14C C14B H14D . . 111.3 ?
C14B C15B H15D . . 109.5 ?
C14B C15B H15E . . 109.5 ?
H15D C15B H15E . . 109.5 ?
C14B C15B H15F . . 109.5 ?
H15D C15B H15F . . 109.5 ?
H15E C15B H15F . . 109.5 ?
N2B C16B C17B . . 114.2(6) ?
N2B C16B H16C . . 108.7 ?
C17B C16B H16C . . 108.7 ?
N2B C16B H16D . . 108.7 ?
C17B C16B H16D . . 108.7 ?
H16C C16B H16D . . 107.6 ?
C16B C17B H17D . . 109.5 ?
C16B C17B H17E . . 109.5 ?
H17D C17B H17E . . 109.5 ?
C16B C17B H17F . . 109.5 ?
H17D C17B H17F . . 109.5 ?
H17E C17B H17F . . 109.5 ?
C11B C18B H18D . . 109.5 ?
C11B C18B H18E . . 109.5 ?
H18D C18B H18E . . 109.5 ?
C11B C18B H18F . . 109.5 ?
H18D C18B H18F . . 109.5 ?
H18E C18B H18F . . 109.5 ?
O2B N3B O3B . . 120.2(13) ?
O2B N3B C10B . . 118.2(9) ?
O3B N3B C10B . . 120.4(11) ?
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 C1A . 1.346(7) ?
O1A H1A . 0.8400 ?
C1A C2A . 1.384(7) ?
C1A C6A . 1.427(7) ?
C2A C3A . 1.420(8) ?
C2A H2AA . 0.9500 ?
C3A N2A . 1.363(4) ?
C3A C4A . 1.433(5) ?
C4A C5A . 1.373(6) ?
C4A H4AA . 0.9500 ?
C5A C6A . 1.409(7) ?
C5A H5AA . 0.9500 ?
C6A C7A . 1.436(7) ?
C7A N1A . 1.299(7) ?
C7A H7AA . 0.9500 ?
N1A C8A . 1.419(7) ?
C8A C9A . 1.388(7) ?
C8A C13A . 1.413(7) ?
C9A C10A . 1.383(7) ?
C9A H9AA . 0.9500 ?
C10A C11A . 1.403(6) ?
C10A N3A . 1.474(7) ?
C11A C12A . 1.394(7) ?
C11A C18A . 1.493(7) ?
C12A C13A . 1.384(7) ?
C12A H12A . 0.9500 ?
C13A H13A . 0.9500 ?
N2A C16A . 1.462(6) ?
N2A C14A . 1.670(3) ?
C14A C15A . 1.526(3) ?
C14A H14A . 0.9900 ?
C14A H14B . 0.9900 ?
C15A H15A . 0.9800 ?
C15A H15B . 0.9800 ?
C15A H15C . 0.9800 ?
C16A C17A . 1.501(6) ?
C16A H16A . 0.9900 ?
C16A H16B . 0.9900 ?
C17A H17A . 0.9800 ?
C17A H17B . 0.9800 ?
C17A H17C . 0.9800 ?
C18A H18A . 0.9800 ?
C18A H18B . 0.9800 ?
C18A H18C . 0.9800 ?
N3A O3A . 1.219(10) ?
N3A O2A . 1.220(7) ?
O1B C1B . 1.376(9) ?
O1B H1B . 0.8400 ?
C1B C2B . 1.377(10) ?
C1B C6B . 1.406(9) ?
C2B C3B . 1.418(10) ?
C2B H2BA . 0.9500 ?
C3B N2B . 1.371(5) ?
C3B C4B . 1.420(6) ?
C4B C5B . 1.361(8) ?
C4B H4BA . 0.9500 ?
C5B C6B . 1.391(8) ?
C5B H5BA . 0.9500 ?
C6B C7B . 1.409(9) ?
C7B N1B . 1.301(9) ?
C7B H7BA . 0.9500 ?
N1B C8B . 1.410(9) ?
C8B C13B . 1.363(9) ?
C8B C9B . 1.401(9) ?
C9B C10B . 1.375(9) ?
C9B H9BA . 0.9500 ?
C10B C11B . 1.405(8) ?
C10B N3B . 1.484(9) ?
C11B C12B . 1.410(9) ?
C11B C18B . 1.512(9) ?
C12B C13B . 1.373(9) ?
C12B H12B . 0.9500 ?
C13B H13B . 0.9500 ?
N2B C16B . 1.463(8) ?
N2B C14B . 1.779(4) ?
C14B C15B . 1.501(4) ?
C14B H14C . 0.9900 ?
C14B H14D . 0.9900 ?
C15B H15D . 0.9800 ?
C15B H15E . 0.9800 ?
C15B H15F . 0.9800 ?
C16B C17B . 1.518(8) ?
C16B H16C . 0.9900 ?
C16B H16D . 0.9900 ?
C17B H17D . 0.9800 ?
C17B H17E . 0.9800 ?
C17B H17F . 0.9800 ?
C18B H18D . 0.9800 ?
C18B H18E . 0.9800 ?
C18B H18F . 0.9800 ?
N3B O2B . 1.225(9) ?
N3B O3B . 1.242(13) ?
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
O1A H1A N1A . 0.8400 1.9500 2.68(2) 144.00 y
C12A H12A O1A 3_557 0.9500 2.5300 3.329(19) 141.00 y
C15A H15A O3A 2_656 0.9800 2.2600 2.983(5) 130.00 y
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
O1A C1A C2A C3A . . . . -171(2) ?
C6A C1A C2A C3A . . . . 2(3) ?
C1A C2A C3A N2A . . . . 178.0(16) ?
C1A C2A C3A C4A . . . . -5(3) ?
N2A C3A C4A C5A . . . . -178.9(4) ?
C2A C3A C4A C5A . . . . 3.6(15) ?
C3A C4A C5A C6A . . . . -0.3(12) ?
C4A C5A C6A C1A . . . . -2(2) ?
C4A C5A C6A C7A . . . . 178.3(10) ?
O1A C1A C6A C5A . . . . 174.7(16) ?
C2A C1A C6A C5A . . . . 1(2) ?
O1A C1A C6A C7A . . . . -6(2) ?
C2A C1A C6A C7A . . . . -179(2) ?
C5A C6A C7A N1A . . . . -174.8(13) ?
C1A C6A C7A N1A . . . . 6(2) ?
C6A C7A N1A C8A . . . . 175.0(14) ?
C7A N1A C8A C9A . . . . 3(2) ?
C7A N1A C8A C13A . . . . -176.6(12) ?
C13A C8A C9A C10A . . . . 0(2) ?
N1A C8A C9A C10A . . . . -179.3(13) ?
C8A C9A C10A C11A . . . . -2(2) ?
C8A C9A C10A N3A . . . . 179(2) ?
C9A C10A C11A C12A . . . . 4.5(19) ?
N3A C10A C11A C12A . . . . -177(2) ?
C9A C10A C11A C18A . . . . -178.9(13) ?
N3A C10A C11A C18A . . . . 0(3) ?
C10A C11A C12A C13A . . . . -6.6(19) ?
C18A C11A C12A C13A . . . . 176.6(12) ?
C11A C12A C13A C8A . . . . 6(2) ?
C9A C8A C13A C12A . . . . -2.3(19) ?
N1A C8A C13A C12A . . . . 177.4(11) ?
C2A C3A N2A C16A . . . . 3.6(16) ?
C4A C3A N2A C16A . . . . -173.8(3) ?
C2A C3A N2A C14A . . . . 143.3(15) ?
C4A C3A N2A C14A . . . . -34.1(4) ?
C3A N2A C14A C15A . . . . 102.7(3) ?
C16A N2A C14A C15A . . . . -112.8(4) ?
C3A N2A C16A C17A . . . . -88.1(6) ?
C14A N2A C16A C17A . . . . 128.8(5) ?
C9A C10A N3A O3A . . . . 175(3) ?
C11A C10A N3A O3A . . . . -4(5) ?
C9A C10A N3A O2A . . . . 5(5) ?
C11A C10A N3A O2A . . . . -174(3) ?
O1B C1B C2B C3B . . . . 166(3) ?
C6B C1B C2B C3B . . . . -5(4) ?
C1B C2B C3B N2B . . . . -176(2) ?
C1B C2B C3B C4B . . . . 8(4) ?
N2B C3B C4B C5B . . . . 178.9(4) ?
C2B C3B C4B C5B . . . . -6(2) ?
C3B C4B C5B C6B . . . . -0.2(16) ?
C4B C5B C6B C1B . . . . 3(3) ?
C4B C5B C6B C7B . . . . -179.4(17) ?
O1B C1B C6B C5B . . . . -172(2) ?
C2B C1B C6B C5B . . . . 0(4) ?
O1B C1B C6B C7B . . . . 11(3) ?
C2B C1B C6B C7B . . . . -178(3) ?
C5B C6B C7B N1B . . . . 179(2) ?
C1B C6B C7B N1B . . . . -4(3) ?
C6B C7B N1B C8B . . . . -177.5(19) ?
C7B N1B C8B C13B . . . . -179.1(17) ?
C7B N1B C8B C9B . . . . -1(3) ?
C13B C8B C9B C10B . . . . 1(3) ?
N1B C8B C9B C10B . . . . -176.9(17) ?
C8B C9B C10B C11B . . . . 1(3) ?
C8B C9B C10B N3B . . . . 177(3) ?
C9B C10B C11B C12B . . . . -6(3) ?
N3B C10B C11B C12B . . . . 177(3) ?
C9B C10B C11B C18B . . . . 177.7(18) ?
N3B C10B C11B C18B . . . . 1(4) ?
C10B C11B C12B C13B . . . . 10(2) ?
C18B C11B C12B C13B . . . . -173.2(15) ?
C9B C8B C13B C12B . . . . 3(3) ?
N1B C8B C13B C12B . . . . -178.4(16) ?
C11B C12B C13B C8B . . . . -9(3) ?
C2B C3B N2B C16B . . . . -4(2) ?
C4B C3B N2B C16B . . . . 170.9(5) ?
C2B C3B N2B C14B . . . . -128(2) ?
C4B C3B N2B C14B . . . . 47.0(3) ?
C3B N2B C14B C15B . . . . -111.2(2) ?
C16B N2B C14B C15B . . . . 116.1(4) ?
C3B N2B C16B C17B . . . . -74.0(9) ?
C14B N2B C16B C17B . . . . 49.9(8) ?
C9B C10B N3B O2B . . . . 2(6) ?
C11B C10B N3B O2B . . . . 179(4) ?
C9B C10B N3B O3B . . . . -166(4) ?
C11B C10B N3B O3B . . . . 11(6) ?
