##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-02-25
_journal_date_accepted     2010-03-02
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      4
_journal_page_first     o776
_journal_page_last     o777
_journal_paper_category     QO
_journal_coeditor_code     WN2378
_publ_contact_author_name     'Prof. Fun, Hoong-Kun'
_publ_contact_author_address
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      MALAYSIA
;
_publ_contact_author_email     'hkfun@usm.my'
_publ_contact_author_fax     '604 6579150'
_publ_contact_author_phone     '604 6533652'
_publ_section_title
;
Ethyl
1-tert-butyl-2-(4-methoxyphenyl)-1H-benzimidazole-5-carboxylate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Natarajan Arumugam' ?
;
      School of Pharmaceutical Sciences
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Shafida Abd Hamid' ?
;
      Kulliyyah of Science,
      International Islamic University Malaysia (IIUM)
      Jalan Istana
      Bandar Indera Mahkota
      25200 Kuantan,
      Pahang
      Malaysia
;
    'Aisyah Saad Abdul Rahim' ?
;
      School of Pharmaceutical Sciences
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Madhukar Hemamalini' ?
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Hoong-Kun Fun'
;
      Thomson Reuters ResearcherID: A-3561-2009.
;
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Ethyl
1-tert-butyl-2-(4-methoxyphenyl)-1H-benzimidazole-5-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H24 N2 O3'
_chemical_formula_sum     'C21 H24 N2 O3'
_chemical_formula_iupac     'C21 H24 N2 O3'
_chemical_formula_weight     352.42
_chemical_melting_point     ?
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     'P n a 21'
_symmetry_space_group_name_Hall     'P 2c -2n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    'x+1/2, -y+1/2, z'
    '-x+1/2, y+1/2, z+1/2'
_cell_length_a     14.3963(7)
_cell_length_b     8.6206(5)
_cell_length_c     15.1609(8)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1881.54(17)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6765
_cell_measurement_theta_min     2.69
_cell_measurement_theta_max     36.86
_cell_measurement_temperature     100.00(10)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.53
_exptl_crystal_size_mid     0.42
_exptl_crystal_size_min     0.27
_exptl_crystal_density_diffrn     1.244
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     752
_exptl_absorpt_coefficient_mu     0.084
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.9570
_exptl_absorpt_correction_T_max     0.9777
_exptl_special_details
;
The crystal was placed in the cold stream of an Oxford Cryosystems Cobra
open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at
100.0(1) K.
;
_diffrn_ambient_temperature     100.00(10)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Bruker APEX DUO CCD area-detector diffractometer
;
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     .
_diffrn_reflns_number     17426
_diffrn_reflns_av_R_equivalents     0.0321
_diffrn_reflns_av_sigmaI/netI     0.0294
_diffrn_reflns_theta_min     2.69
_diffrn_reflns_theta_max     35.00
_diffrn_reflns_theta_full     35.00
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -23
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     4233
_reflns_number_gt     3951
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0453
_refine_ls_R_factor_gt     0.0371
_refine_ls_wR_factor_gt     0.1018
_refine_ls_wR_factor_ref     0.1133
_refine_ls_goodness_of_fit_ref     1.131
_refine_ls_restrained_S_all     1.131
_refine_ls_number_reflns     4233
_refine_ls_number_parameters     240
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0773P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.603
_refine_diff_density_min     -0.574
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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 0.0000
                         '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 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
                             'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
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 O1 0.12374(8) 1.21773(11) 0.18521(7) 0.02061(19) Uani d . 1 . .
    O O2 0.25619(7) 0.09272(11) 0.59077(8) 0.02019(19) Uani d . 1 . .
    O O3 0.11256(7) 0.01389(12) 0.63146(8) 0.02132(19) Uani d . 1 . .
    N N1 0.00387(7) 0.60189(11) 0.40798(7) 0.01307(17) Uani d . 1 . .
    N N2 0.16125(7) 0.58244(12) 0.40296(7) 0.01439(18) Uani d . 1 . .
    C C1 0.07671(9) 0.95165(14) 0.37017(8) 0.0159(2) Uani d . 1 . .
    H H1A 0.0560 0.9522 0.4283 0.019 Uiso calc R 1 . .
    C C2 0.08488(9) 1.09163(14) 0.32461(9) 0.0158(2) Uani d . 1 . .
    H H2A 0.0694 1.1849 0.3518 0.019 Uiso calc R 1 . .
    C C3 0.11669(9) 1.08946(13) 0.23757(8) 0.01465(19) Uani d . 1 . .
    C C4 0.14432(9) 0.95031(14) 0.19836(8) 0.0156(2) Uani d . 1 . .
    H H4A 0.1685 0.9503 0.1415 0.019 Uiso calc R 1 . .
    C C5 0.13556(8) 0.81218(14) 0.24449(8) 0.01461(19) Uani d . 1 . .
    H H5A 0.1541 0.7195 0.2184 0.018 Uiso calc R 1 . .
    C C6 0.09897(8) 0.81128(13) 0.33013(8) 0.01312(18) Uani d . 1 . .
    C C7 0.08802(8) 0.66340(14) 0.37851(8) 0.01293(19) Uani d . 1 . .
    C C8 0.02836(8) 0.47467(13) 0.45937(8) 0.01276(18) Uani d . 1 . .
    C C9 0.12598(8) 0.46271(13) 0.45378(8) 0.01270(18) Uani d . 1 . .
    C C10 0.17417(8) 0.34437(14) 0.49659(8) 0.01382(19) Uani d . 1 . .
    H H10A 0.2384 0.3360 0.4921 0.017 Uiso calc R 1 . .
    C C11 0.12284(8) 0.23910(13) 0.54632(8) 0.01365(18) Uani d . 1 . .
    C C12 0.02572(8) 0.25487(14) 0.55447(8) 0.0156(2) Uani d . 1 . .
    H H12A -0.0068 0.1845 0.5892 0.019 Uiso calc R 1 . .
    C C13 -0.02274(8) 0.37223(14) 0.51221(8) 0.0157(2) Uani d . 1 . .
    H H13A -0.0867 0.3826 0.5187 0.019 Uiso calc R 1 . .
    C C14 0.17224(8) 0.10981(14) 0.59068(9) 0.01472(19) Uani d . 1 . .
    C C15 0.14999(11) -0.12009(16) 0.67719(10) 0.0227(2) Uani d . 1 . .
    H H15A 0.1157 -0.1375 0.7314 0.027 Uiso calc R 1 . .
    H H15B 0.2145 -0.1017 0.6923 0.027 Uiso calc R 1 . .
    C C16 0.14263(14) -0.26002(18) 0.61893(12) 0.0300(3) Uani d . 1 . .
    H H16A 0.1631 -0.3501 0.6507 0.045 Uiso calc R 1 . .
    H H16B 0.1809 -0.2458 0.5677 0.045 Uiso calc R 1 . .
    H H16C 0.0792 -0.2738 0.6010 0.045 Uiso calc R 1 . .
    C C17 -0.09468(8) 0.64670(15) 0.38647(9) 0.0157(2) Uani d . 1 . .
    C C18 -0.14919(10) 0.50058(19) 0.36114(13) 0.0279(3) Uani d . 1 . .
    H H18A -0.1544 0.4337 0.4115 0.042 Uiso calc R 1 . .
    H H18B -0.1172 0.4471 0.3146 0.042 Uiso calc R 1 . .
    H H18C -0.2101 0.5294 0.3414 0.042 Uiso calc R 1 . .
    C C19 -0.13666(11) 0.7233(2) 0.46773(11) 0.0290(3) Uani d . 1 . .
    H H19A -0.0993 0.8106 0.4846 0.044 Uiso calc R 1 . .
    H H19B -0.1386 0.6499 0.5153 0.044 Uiso calc R 1 . .
    H H19C -0.1985 0.7578 0.4545 0.044 Uiso calc R 1 . .
    C C20 -0.10132(11) 0.7557(2) 0.30761(12) 0.0305(4) Uani d . 1 . .
    H H20A -0.0752 0.8545 0.3229 0.046 Uiso calc R 1 . .
    H H20B -0.1653 0.7688 0.2914 0.046 Uiso calc R 1 . .
    H H20C -0.0677 0.7124 0.2588 0.046 Uiso calc R 1 . .
    C C21 0.09176(12) 1.36157(16) 0.22065(10) 0.0232(3) Uani d . 1 . .
    H H21A 0.0965 1.4409 0.1765 0.035 Uiso calc R 1 . .
    H H21B 0.1291 1.3894 0.2707 0.035 Uiso calc R 1 . .
    H H21C 0.0281 1.3511 0.2387 0.035 Uiso calc R 1 . .
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
    O1 C3 . 1.3649(15) ?
    O1 C21 . 1.4277(17) ?
    O2 C14 . 1.2174(15) ?
    O3 C14 . 1.3432(16) ?
    O3 C15 . 1.4509(16) ?
    N1 C8 . 1.3908(15) ?
    N1 C7 . 1.3958(15) ?
    N1 C17 . 1.5061(15) ?
    N2 C7 . 1.3176(15) ?
    N2 C9 . 1.3845(15) ?
    C1 C6 . 1.3912(16) ?
    C1 C2 . 1.3954(17) ?
    C1 H1A . 0.9300 ?
    C2 C3 . 1.3970(18) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.3966(17) ?
    C4 C5 . 1.3868(16) ?
    C4 H4A . 0.9300 ?
    C5 C6 . 1.4011(17) ?
    C5 H5A . 0.9300 ?
    C6 C7 . 1.4792(16) ?
    C8 C13 . 1.4010(16) ?
    C8 C9 . 1.4117(15) ?
    C9 C10 . 1.3941(16) ?
    C10 C11 . 1.3921(16) ?
    C10 H10A . 0.9300 ?
    C11 C12 . 1.4102(16) ?
    C11 C14 . 1.4833(16) ?
    C12 C13 . 1.3860(16) ?
    C12 H12A . 0.9300 ?
    C13 H13A . 0.9300 ?
    C15 C16 . 1.499(2) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
    C17 C19 . 1.523(2) ?
    C17 C20 . 1.5236(19) ?
    C17 C18 . 1.5330(19) ?
    C18 H18A . 0.9600 ?
    C18 H18B . 0.9600 ?
    C18 H18C . 0.9600 ?
    C19 H19A . 0.9600 ?
    C19 H19B . 0.9600 ?
    C19 H19C . 0.9600 ?
    C20 H20A . 0.9600 ?
    C20 H20B . 0.9600 ?
    C20 H20C . 0.9600 ?
    C21 H21A . 0.9600 ?
    C21 H21B . 0.9600 ?
    C21 H21C . 0.9600 ?
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
    C3 O1 C21 . . 117.44(11) ?
    C14 O3 C15 . . 118.20(11) ?
    C8 N1 C7 . . 105.00(9) ?
    C8 N1 C17 . . 124.22(9) ?
    C7 N1 C17 . . 130.60(10) ?
    C7 N2 C9 . . 104.95(10) ?
    C6 C1 C2 . . 121.12(11) ?
    C6 C1 H1A . . 119.4 ?
    C2 C1 H1A . . 119.4 ?
    C1 C2 C3 . . 118.93(11) ?
    C1 C2 H2A . . 120.5 ?
    C3 C2 H2A . . 120.5 ?
    O1 C3 C4 . . 115.29(11) ?
    O1 C3 C2 . . 124.26(11) ?
    C4 C3 C2 . . 120.46(11) ?
    C5 C4 C3 . . 119.80(11) ?
    C5 C4 H4A . . 120.1 ?
    C3 C4 H4A . . 120.1 ?
    C4 C5 C6 . . 120.42(11) ?
    C4 C5 H5A . . 119.8 ?
    C6 C5 H5A . . 119.8 ?
    C1 C6 C5 . . 119.08(11) ?
    C1 C6 C7 . . 120.58(10) ?
    C5 C6 C7 . . 120.29(10) ?
    N2 C7 N1 . . 113.78(10) ?
    N2 C7 C6 . . 120.71(10) ?
    N1 C7 C6 . . 125.36(10) ?
    N1 C8 C13 . . 133.18(10) ?
    N1 C8 C9 . . 106.04(10) ?
    C13 C8 C9 . . 120.74(10) ?
    N2 C9 C10 . . 128.47(10) ?
    N2 C9 C8 . . 110.13(10) ?
    C10 C9 C8 . . 121.39(10) ?
    C11 C10 C9 . . 117.71(10) ?
    C11 C10 H10A . . 121.1 ?
    C9 C10 H10A . . 121.1 ?
    C10 C11 C12 . . 120.73(10) ?
    C10 C11 C14 . . 118.74(10) ?
    C12 C11 C14 . . 120.53(10) ?
    C13 C12 C11 . . 121.94(11) ?
    C13 C12 H12A . . 119.0 ?
    C11 C12 H12A . . 119.0 ?
    C12 C13 C8 . . 117.39(10) ?
    C12 C13 H13A . . 121.3 ?
    C8 C13 H13A . . 121.3 ?
    O2 C14 O3 . . 124.05(11) ?
    O2 C14 C11 . . 124.57(11) ?
    O3 C14 C11 . . 111.38(10) ?
    O3 C15 C16 . . 109.43(13) ?
    O3 C15 H15A . . 109.8 ?
    C16 C15 H15A . . 109.8 ?
    O3 C15 H15B . . 109.8 ?
    C16 C15 H15B . . 109.8 ?
    H15A C15 H15B . . 108.2 ?
    C15 C16 H16A . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C15 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    N1 C17 C19 . . 108.05(11) ?
    N1 C17 C20 . . 112.78(10) ?
    C19 C17 C20 . . 110.03(13) ?
    N1 C17 C18 . . 109.01(10) ?
    C19 C17 C18 . . 110.85(13) ?
    C20 C17 C18 . . 106.14(12) ?
    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 ?
    C17 C19 H19A . . 109.5 ?
    C17 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C17 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    C17 C20 H20A . . 109.5 ?
    C17 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    C17 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    O1 C21 H21A . . 109.5 ?
    O1 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    O1 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
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
    C6 C1 C2 C3 . . . . -0.48(19) ?
    C21 O1 C3 C4 . . . . 176.78(12) ?
    C21 O1 C3 C2 . . . . -3.48(19) ?
    C1 C2 C3 O1 . . . . 177.04(12) ?
    C1 C2 C3 C4 . . . . -3.22(18) ?
    O1 C3 C4 C5 . . . . -176.84(11) ?
    C2 C3 C4 C5 . . . . 3.40(18) ?
    C3 C4 C5 C6 . . . . 0.13(18) ?
    C2 C1 C6 C5 . . . . 3.95(18) ?
    C2 C1 C6 C7 . . . . -178.63(11) ?
    C4 C5 C6 C1 . . . . -3.76(17) ?
    C4 C5 C6 C7 . . . . 178.81(11) ?
    C9 N2 C7 N1 . . . . -1.88(14) ?
    C9 N2 C7 C6 . . . . 173.81(11) ?
    C8 N1 C7 N2 . . . . 3.19(14) ?
    C17 N1 C7 N2 . . . . -172.05(11) ?
    C8 N1 C7 C6 . . . . -172.26(11) ?
    C17 N1 C7 C6 . . . . 12.49(19) ?
    C1 C6 C7 N2 . . . . -110.78(14) ?
    C5 C6 C7 N2 . . . . 66.61(15) ?
    C1 C6 C7 N1 . . . . 64.39(16) ?
    C5 C6 C7 N1 . . . . -118.22(13) ?
    C7 N1 C8 C13 . . . . 174.46(13) ?
    C17 N1 C8 C13 . . . . -9.9(2) ?
    C7 N1 C8 C9 . . . . -3.02(12) ?
    C17 N1 C8 C9 . . . . 172.61(11) ?
    C7 N2 C9 C10 . . . . -179.31(12) ?
    C7 N2 C9 C8 . . . . -0.18(13) ?
    N1 C8 C9 N2 . . . . 2.09(13) ?
    C13 C8 C9 N2 . . . . -175.77(11) ?
    N1 C8 C9 C10 . . . . -178.71(11) ?
    C13 C8 C9 C10 . . . . 3.43(18) ?
    N2 C9 C10 C11 . . . . 178.14(12) ?
    C8 C9 C10 C11 . . . . -0.90(18) ?
    C9 C10 C11 C12 . . . . -1.53(18) ?
    C9 C10 C11 C14 . . . . 178.49(11) ?
    C10 C11 C12 C13 . . . . 1.53(19) ?
    C14 C11 C12 C13 . . . . -178.48(12) ?
    C11 C12 C13 C8 . . . . 0.94(19) ?
    N1 C8 C13 C12 . . . . 179.47(12) ?
    C9 C8 C13 C12 . . . . -3.35(18) ?
    C15 O3 C14 O2 . . . . -1.2(2) ?
    C15 O3 C14 C11 . . . . 179.23(11) ?
    C10 C11 C14 O2 . . . . 4.03(19) ?
    C12 C11 C14 O2 . . . . -175.95(13) ?
    C10 C11 C14 O3 . . . . -176.36(11) ?
    C12 C11 C14 O3 . . . . 3.65(16) ?
    C14 O3 C15 C16 . . . . -97.76(15) ?
    C8 N1 C17 C19 . . . . 76.40(15) ?
    C7 N1 C17 C19 . . . . -109.15(15) ?
    C8 N1 C17 C20 . . . . -161.76(13) ?
    C7 N1 C17 C20 . . . . 12.69(19) ?
    C8 N1 C17 C18 . . . . -44.15(16) ?
    C7 N1 C17 C18 . . . . 130.30(14) ?
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
    C5 H5A O2 4_554 0.9300 2.5700 3.3822(16) 146.00 yes
    C13 H13A O2 3_455 0.9300 2.5200 3.4116(16) 160.00 yes
    C19 H19C N2 3_465 0.9600 2.5700 3.4976(19) 164.00 yes
    C2 H2A Cg3 1_565 0.9300 2.7500 3.5594(14) 146.00 yes
    C18 H18C Cg2 4_465 0.9600 2.7400 3.6878(16) 168.00 yes
    C21 H21B Cg1 1_565 0.9600 2.7800 3.4703(16) 130.00 yes
