#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/44/2104401.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_2104401
loop_
_publ_author_name
'Chan, Eric J.'
'Rae, A. David'
'Welberry, T. Richard'
_publ_section_title
;
 On the polymorphism of benzocaine; a low-temperature structural phase
 transition for form (II)
;
_journal_coeditor_code           SO5027
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              509
_journal_page_last               515
_journal_paper_doi               10.1107/S0108768109018898
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C9 H11 N O2'
_chemical_formula_sum            'C9 H11 N O2'
_chemical_formula_weight         165.19
_chemical_name_common            Benzocaine
_chemical_name_systematic
;
ethyl 4-aminobenzoate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2c'
_symmetry_space_group_name_H-M   'P 1 1 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'packing arguments'
_atom_sites_solution_secondary   'packing arguments'
_audit_creation_method           RAELS2006
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                99.370(2)
_cell_formula_units_Z            8
_cell_length_a                   8.1883(4)
_cell_length_b                   10.6394(5)
_cell_length_c                   20.4761(10)
_cell_measurement_reflns_used    156810
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.546
_cell_volume                     1760.05(15)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XTAL3.7 (Hall et al., 2001)'
_computing_publication_material  'XTAL3.7 (Hall et al., 2001)'
_computing_structure_refinement  'RAELS2006 (Rae, 2006)'
_computing_structure_solution    'Packing arguments'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.063
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24960
_diffrn_reflns_theta_full        25.365
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         6013
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.115
_refine_ls_R_factor_gt           0.065
_refine_ls_shift/su_max          0.01
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'calc w=1/[σ²(F)+(0.03F)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.091
_refine_ls_wR_factor_ref         0.098
_reflns_number_gt                6013
_reflns_number_total             7859
_reflns_threshold_expression     'I > 3 sigma(I)'
_cod_data_source_file            so5027.cif
_cod_data_source_block           III
_cod_database_code               2104401
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, 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_calc_flag
_atom_site_calc_attached_atom
_atom_site_occupancy
C C11 0.5566(2) 0.32209(15) 0.36344(6) 0.0272(4) d . 1.000
C C12 0.5277(2) 0.21927(19) 0.32048(9) 0.0311(4) d . 1.000
C C13 0.3693(2) 0.17263(17) 0.29933(9) 0.0304(4) d . 1.000
C C14 0.2346(2) 0.22807(15) 0.32077(8) 0.0287(4) d . 1.000
C C15 0.2645(2) 0.33153(18) 0.36400(10) 0.0304(4) d . 1.000
C C16 0.4233(2) 0.37753(17) 0.38490(9) 0.0283(4) d . 1.000
C C17 0.7276(3) 0.3689(2) 0.38480(10) 0.0312(4) d . 1.000
O O18 0.8487(3) 0.3239(3) 0.36865(13) 0.0401(5) d . 1.000
O O19 0.7374(3) 0.4651(2) 0.42774(12) 0.0325(4) d . 1.000
C C110 0.9029(4) 0.5163(4) 0.45196(19) 0.0394(6) d . 1.000
C C111 0.8810(5) 0.6131(4) 0.5028(2) 0.0470(11) d . 1.000
N N112 0.0767(2) 0.1822(2) 0.29996(11) 0.0337(4) d . 1.000
C C21 0.7047(2) 0.56163(15) 0.13936(7) 0.0285(4) d . 1.000
C C22 0.6906(2) 0.45818(19) 0.18190(9) 0.0313(4) d . 1.000
C C23 0.8298(2) 0.41356(17) 0.20404(9) 0.0298(5) d . 1.000
C C24 0.9880(2) 0.47171(15) 0.18405(8) 0.0291(5) d . 1.000
C C25 1.0015(2) 0.57579(18) 0.14123(10) 0.0309(5) d . 1.000
C C26 0.8616(2) 0.61977(17) 0.11934(9) 0.0287(5) d . 1.000
C C27 0.5530(3) 0.6062(2) 0.11691(10) 0.0329(4) d . 1.000
O O28 0.4131(3) 0.5538(2) 0.13033(14) 0.0420(7) d . 1.000
O O29 0.5813(3) 0.7059(2) 0.07689(12) 0.0328(4) d . 1.000
C C210 0.4357(4) 0.7532(4) 0.0525(2) 0.0395(6) d . 1.000
C C211 0.4938(5) 0.8655(4) 0.0093(2) 0.0425(9) d . 1.000
N N212 1.1271(2) 0.4279(2) 0.20586(11) 0.0336(6) d . 1.000
C C31 0.7033(2) 0.81687(16) 0.35695(6) 0.0281(5) d . 1.000
C C32 0.6712(2) 0.70534(19) 0.32019(9) 0.0308(5) d . 1.000
C C33 0.5130(2) 0.65943(17) 0.29862(9) 0.0301(5) d . 1.000
C C34 0.3817(2) 0.72441(15) 0.31339(8) 0.0301(4) d . 1.000
C C35 0.4146(2) 0.83662(18) 0.35040(10) 0.0338(4) d . 1.000
C C36 0.5733(2) 0.88181(17) 0.37176(9) 0.0310(4) d . 1.000
C C37 0.8740(3) 0.8625(2) 0.37898(10) 0.0310(5) d . 1.000
O O38 0.9935(3) 0.8136(2) 0.36615(13) 0.0386(6) d . 1.000
O O39 0.8832(3) 0.9591(2) 0.42229(12) 0.0324(4) d . 1.000
C C310 1.0443(4) 1.0066(3) 0.44995(18) 0.0371(5) d . 1.000
C C311 1.0274(5) 1.1221(4) 0.4900(2) 0.0448(6) d . 1.000
N N312 0.2239(2) 0.6794(2) 0.29212(11) 0.0346(5) d . 1.000
C C41 0.8234(2) 0.06483(16) 0.14551(6) 0.0303(4) d . 1.000
C C42 0.8084(2) -0.04434(19) 0.18410(9) 0.0332(4) d . 1.000
C C43 0.9458(2) -0.09817(17) 0.19974(9) 0.0323(4) d . 1.000
C C44 1.1031(2) -0.04379(16) 0.17699(8) 0.0320(4) d . 1.000
C C45 1.1175(2) 0.06608(19) 0.13816(10) 0.0344(5) d . 1.000
C C46 0.9794(2) 0.11926(18) 0.12278(9) 0.0318(5) d . 1.000
C C47 0.6736(3) 0.1192(2) 0.12998(11) 0.0341(4) d . 1.000
O O48 0.5359(3) 0.0809(3) 0.15084(14) 0.0427(5) d . 1.000
O O49 0.6984(3) 0.1995(2) 0.07735(12) 0.0351(5) d . 1.000
C C410 0.5552(5) 0.2492(4) 0.0535(2) 0.0414(7) d . 1.000
C C411 0.6131(5) 0.3457(4) 0.0019(2) 0.0474(9) d . 1.000
N N412 1.2404(2) -0.0968(2) 0.19233(12) 0.0370(5) d . 1.000
H H1C12 0.62256 0.17886 0.30482 0.040 c C12 1.000
H H1C13 0.35037 0.09879 0.26850 0.037 c C13 1.000
H H1C15 0.17003 0.37228 0.37982 0.039 c C15 1.000
H H1C16 0.44288 0.45135 0.41572 0.033 c C16 1.000
H H1C110 0.97365 0.55727 0.41552 0.045 c C110 1.000
H H2C110 0.95558 0.44670 0.47158 0.042 c C110 1.000
H H1C111 0.99152 0.65103 0.52088 0.053 c C111 1.000
H H2C111 0.82744 0.68183 0.48271 0.052 c C111 1.000
H H3C111 0.80937 0.57126 0.53877 0.049 c C111 1.000
H H1N112 0.05655 0.10843 0.26913 0.036 c N112 1.000
H H2N112 -0.01816 0.22267 0.31563 0.040 c N112 1.000
H H1C22 0.57853 0.41585 0.19654 0.039 c C22 1.000
H H1C23 0.81776 0.33923 0.23456 0.034 c C23 1.000
H H1C25 1.11328 0.61846 0.12644 0.038 c C25 1.000
H H1C26 0.87297 0.69406 0.08882 0.032 c C26 1.000
H H1C210 0.37064 0.77985 0.08991 0.046 c C210 1.000
H H2C210 0.36486 0.68499 0.02696 0.042 c C210 1.000
H H1C211 0.39592 0.89992 -0.00816 0.048 c C211 1.000
H H2C211 0.56501 0.93313 0.03509 0.046 c C211 1.000
H H3C211 0.55924 0.83828 -0.02787 0.042 c C211 1.000
H H1N212 1.11632 0.35362 0.23638 0.034 c N212 1.000
H H2N212 1.23914 0.47024 0.19121 0.040 c N212 1.000
H H1C32 0.76374 0.65808 0.30932 0.038 c C32 1.000
H H1C33 0.49181 0.57927 0.27229 0.035 c C33 1.000
H H1C35 0.32258 0.88423 0.36140 0.044 c C35 1.000
H H1C36 0.59513 0.96193 0.39811 0.037 c C36 1.000
H H1C310 1.12686 1.03034 0.41423 0.039 c C310 1.000
H H2C310 1.08117 0.93998 0.47827 0.041 c C310 1.000
H H1C311 1.13687 1.15742 0.50989 0.049 c C311 1.000
H H2C311 0.98994 1.18805 0.46140 0.048 c C311 1.000
H H3C311 0.94424 1.09769 0.52545 0.050 c C311 1.000
H H1N312 0.20149 0.59929 0.26576 0.035 c N312 1.000
H H2N312 0.13141 0.72665 0.30300 0.042 c N312 1.000
H H1C42 0.69697 -0.08407 0.20064 0.041 c C42 1.000
H H1C43 0.93313 -0.17652 0.22748 0.037 c C43 1.000
H H1C45 1.22863 0.10619 0.12150 0.043 c C45 1.000
H H1C46 0.99139 0.19760 0.09505 0.036 c C46 1.000
H H1C410 0.50238 0.29026 0.09009 0.044 c C410 1.000
H H2C410 0.47321 0.17861 0.03461 0.047 c C410 1.000
H H1C411 0.51652 0.38178 -0.01553 0.053 c C411 1.000
H H2C411 0.69542 0.41568 0.02110 0.049 c C411 1.000
H H3C411 0.66625 0.30402 -0.03439 0.052 c C411 1.000
H H1N412 1.22896 -0.17510 0.22004 0.038 c N412 1.000
H H2N412 1.35177 -0.05700 0.17578 0.044 c N412 1.000
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 C11 C16 . . . 119.10(10) .
C12 C11 C17 . . . 118.90(10) .
C16 C11 C17 . . . 122.00(10) .
C11 C12 C13 . . . 120.60(10) .
C12 C13 C14 . . . 120.50(10) .
C13 C14 C15 . . . 118.60(10) .
C13 C14 N112 . . . 120.80(10) .
C15 C14 N112 . . . 120.50(10) .
C14 C15 C16 . . . 120.50(10) .
C11 C16 C15 . . . 120.60(10) .
C11 C17 O18 . . . 125.3(2) .
C11 C17 O19 . . . 112.8(2) .
O18 C17 O19 . . . 121.8(2) .
C17 O19 C110 . . . 116.3(2) .
O19 C110 C111 . . . 106.6(3) .
C22 C21 C26 . . . 119.10(10) .
C22 C21 C27 . . . 118.90(10) .
C26 C21 C27 . . . 122.00(10) .
C21 C22 C23 . . . 120.60(10) .
C22 C23 C24 . . . 120.50(10) .
C23 C24 C25 . . . 118.60(10) .
C23 C24 N212 . . . 120.80(10) .
C25 C24 N212 . . . 120.50(10) .
C24 C25 C26 . . . 120.50(10) .
C21 C26 C25 . . . 120.60(10) .
C21 C27 O28 . . . 124.1(2) .
C21 C27 O29 . . . 113.7(2) .
O28 C27 O29 . . . 122.1(2) .
C27 O29 C210 . . . 116.1(2) .
O29 C210 C211 . . . 107.8(3) .
C32 C31 C36 . . . 119.10(10) .
C32 C31 C37 . . . 118.90(10) .
C36 C31 C37 . . . 122.00(10) .
C31 C32 C33 . . . 120.60(10) .
C32 C33 C34 . . . 120.50(10) .
C33 C34 C35 . . . 118.60(10) .
C33 C34 N312 . . . 120.80(10) .
C35 C34 N312 . . . 120.50(10) .
C34 C35 C36 . . . 120.50(10) .
C31 C36 C35 . . . 120.60(10) .
C31 C37 O38 . . . 125.6(2) .
C31 C37 O39 . . . 112.6(2) .
O38 C37 O39 . . . 121.5(2) .
C37 O39 C310 . . . 117.2(2) .
O39 C310 C311 . . . 107.4(3) .
C42 C41 C46 . . . 119.10(10) .
C42 C41 C47 . . . 118.90(10) .
C46 C41 C47 . . . 122.00(10) .
C41 C42 C43 . . . 120.60(10) .
C42 C43 C44 . . . 120.50(10) .
C43 C44 C45 . . . 118.60(10) .
C43 C44 N412 . . . 120.80(10) .
C45 C44 N412 . . . 120.50(10) .
C44 C45 C46 . . . 120.50(10) .
C41 C46 C45 . . . 120.60(10) .
C41 C47 O48 . . . 125.4(2) .
C41 C47 O49 . . . 111.5(2) .
O48 C47 O49 . . . 121.5(2) .
C47 O49 C410 . . . 116.5(2) .
O49 C410 C411 . . . 107.7(3) .
C11 C12 H1C12 . . . 119.7 .
C13 C12 H1C12 . . . 119.7 .
C12 C13 H1C13 . . . 119.8 .
C14 C13 H1C13 . . . 119.8 .
C14 C15 H1C15 . . . 119.8 .
C16 C15 H1C15 . . . 119.8 .
C11 C16 H1C16 . . . 119.7 .
C15 C16 H1C16 . . . 119.7 .
O19 C110 H1C110 . . . 110.2 .
O19 C110 H2C110 . . . 110.2 .
C111 C110 H1C110 . . . 110.2 .
C111 C110 H2C110 . . . 110.2 .
H1C110 C110 H2C110 . . . 109.5 .
C110 C111 H1C111 . . . 109.5 .
C110 C111 H2C111 . . . 109.5 .
C110 C111 H3C111 . . . 109.5 .
H1C111 C111 H2C111 . . . 109.5 .
H1C111 C111 H3C111 . . . 109.5 .
H2C111 C111 H3C111 . . . 109.5 .
C14 N112 H1N112 . . . 120.0 .
C14 N112 H2N112 . . . 120.0 .
H1N112 N112 H2N112 . . . 120.0 .
C21 C22 H1C22 . . . 119.7 .
C23 C22 H1C22 . . . 119.7 .
C22 C23 H1C23 . . . 119.8 .
C24 C23 H1C23 . . . 119.8 .
C24 C25 H1C25 . . . 119.8 .
C26 C25 H1C25 . . . 119.8 .
C21 C26 H1C26 . . . 119.7 .
C25 C26 H1C26 . . . 119.7 .
O29 C210 H1C210 . . . 109.9 .
O29 C210 H2C210 . . . 109.9 .
C211 C210 H1C210 . . . 109.9 .
C211 C210 H2C210 . . . 109.9 .
H1C210 C210 H2C210 . . . 109.5 .
C210 C211 H1C211 . . . 109.5 .
C210 C211 H2C211 . . . 109.5 .
C210 C211 H3C211 . . . 109.5 .
H1C211 C211 H2C211 . . . 109.5 .
H1C211 C211 H3C211 . . . 109.5 .
H2C211 C211 H3C211 . . . 109.5 .
C24 N212 H1N212 . . . 120.0 .
C24 N212 H2N212 . . . 120.0 .
H1N212 N212 H2N212 . . . 120.0 .
C31 C32 H1C32 . . . 119.7 .
C33 C32 H1C32 . . . 119.7 .
C32 C33 H1C33 . . . 119.8 .
C34 C33 H1C33 . . . 119.8 .
C34 C35 H1C35 . . . 119.8 .
C36 C35 H1C35 . . . 119.8 .
C31 C36 H1C36 . . . 119.7 .
C35 C36 H1C36 . . . 119.7 .
O39 C310 H1C310 . . . 110.0 .
O39 C310 H2C310 . . . 110.0 .
C311 C310 H1C310 . . . 110.0 .
C311 C310 H2C310 . . . 110.0 .
H1C310 C310 H2C310 . . . 109.5 .
C310 C311 H1C311 . . . 109.5 .
C310 C311 H2C311 . . . 109.5 .
C310 C311 H3C311 . . . 109.5 .
H1C311 C311 H2C311 . . . 109.5 .
H1C311 C311 H3C311 . . . 109.5 .
H2C311 C311 H3C311 . . . 109.5 .
C34 N312 H1N312 . . . 120.0 .
C34 N312 H2N312 . . . 120.0 .
H1N312 N312 H2N312 . . . 120.0 .
C41 C42 H1C42 . . . 119.7 .
C43 C42 H1C42 . . . 119.7 .
C42 C43 H1C43 . . . 119.8 .
C44 C43 H1C43 . . . 119.8 .
C44 C45 H1C45 . . . 119.8 .
C46 C45 H1C45 . . . 119.8 .
C41 C46 H1C46 . . . 119.7 .
C45 C46 H1C46 . . . 119.7 .
O49 C410 H1C410 . . . 109.9 .
O49 C410 H2C410 . . . 109.9 .
C411 C410 H1C410 . . . 109.9 .
C411 C410 H2C410 . . . 109.9 .
H1C410 C410 H2C410 . . . 109.5 .
C410 C411 H1C411 . . . 109.5 .
C410 C411 H2C411 . . . 109.5 .
C410 C411 H3C411 . . . 109.5 .
H1C411 C411 H2C411 . . . 109.5 .
H1C411 C411 H3C411 . . . 109.5 .
H2C411 C411 H3C411 . . . 109.5 .
C44 N412 H1N412 . . . 120.0 .
C44 N412 H2N412 . . . 120.0 .
H1N412 N412 H2N412 . . . 120.0 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C11 C12 . . 1.3940(10) .
C11 C16 . . 1.3940(10) .
C11 C17 . . 1.474(2) .
C12 C13 . . 1.381(2) .
C13 C14 . . 1.4030(10) .
C14 C15 . . 1.4030(10) .
C14 N112 . . 1.373(2) .
C15 C16 . . 1.381(2) .
C17 O18 . . 1.215(3) .
C17 O19 . . 1.342(3) .
O19 C110 . . 1.463(4) .
C110 C111 . . 1.495(6) .
C21 C22 . . 1.3940(10) .
C21 C26 . . 1.3940(10) .
C21 C27 . . 1.474(2) .
C22 C23 . . 1.381(2) .
C23 C24 . . 1.4030(10) .
C24 C25 . . 1.4030(10) .
C24 N212 . . 1.373(2) .
C25 C26 . . 1.381(2) .
C27 O28 . . 1.221(3) .
C27 O29 . . 1.330(3) .
O29 C210 . . 1.455(4) .
C210 C211 . . 1.501(5) .
C31 C32 . . 1.3940(10) .
C31 C36 . . 1.3940(10) .
C31 C37 . . 1.474(2) .
C32 C33 . . 1.381(2) .
C33 C34 . . 1.4030(10) .
C34 C35 . . 1.4030(10) .
C34 N312 . . 1.373(2) .
C35 C36 . . 1.381(2) .
C37 O38 . . 1.210(3) .
C37 O39 . . 1.350(3) .
O39 C310 . . 1.449(4) .
C310 C311 . . 1.502(5) .
C41 C42 . . 1.3940(10) .
C41 C46 . . 1.3940(10) .
C41 C47 . . 1.474(2) .
C42 C43 . . 1.381(2) .
C43 C44 . . 1.4030(10) .
C44 C45 . . 1.4030(10) .
C44 N412 . . 1.373(2) .
C45 C46 . . 1.381(2) .
C47 O48 . . 1.212(3) .
C47 O49 . . 1.369(3) .
O49 C410 . . 1.447(4) .
C410 C411 . . 1.496(5) .
C12 H1C12 . . 1.000 .
C13 H1C13 . . 1.000 .
C15 H1C15 . . 1.000 .
C16 H1C16 . . 1.000 .
C110 H1C110 . . 1.000 .
C110 H2C110 . . 1.000 .
C111 H1C111 . . 1.000 .
C111 H2C111 . . 1.000 .
C111 H3C111 . . 1.000 .
N112 H1N112 . . 1.000 .
N112 H2N112 . . 1.000 .
C22 H1C22 . . 1.000 .
C23 H1C23 . . 1.000 .
C25 H1C25 . . 1.000 .
C26 H1C26 . . 1.000 .
C210 H1C210 . . 1.000 .
C210 H2C210 . . 1.000 .
C211 H1C211 . . 1.000 .
C211 H2C211 . . 1.000 .
C211 H3C211 . . 1.000 .
N212 H1N212 . . 1.000 .
N212 H2N212 . . 1.000 .
C32 H1C32 . . 1.000 .
C33 H1C33 . . 1.000 .
C35 H1C35 . . 1.000 .
C36 H1C36 . . 1.000 .
C310 H1C310 . . 1.000 .
C310 H2C310 . . 1.000 .
C311 H1C311 . . 1.000 .
C311 H2C311 . . 1.000 .
C311 H3C311 . . 1.000 .
N312 H1N312 . . 1.000 .
N312 H2N312 . . 1.000 .
C42 H1C42 . . 1.000 .
C43 H1C43 . . 1.000 .
C45 H1C45 . . 1.000 .
C46 H1C46 . . 1.000 .
C410 H1C410 . . 1.000 .
C410 H2C410 . . 1.000 .
C411 H1C411 . . 1.000 .
C411 H2C411 . . 1.000 .
C411 H3C411 . . 1.000 .
N412 H1N412 . . 1.000 .
N412 H2N412 . . 1.000 .
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
C11 C211 3.578(4) . 2_665 .
C13 O48 3.535(3) . . .
C14 N212 3.382(3) . 1_455 .
C15 O18 3.393(3) . 1_455 .
C16 C33 3.455(3) . . .
O18 N112 2.941(3) . 1_655 .
O18 C23 3.513(3) . . .
O19 C210 3.586(4) . 2_665 .
O19 C32 3.483(3) . . .
C110 O38 3.588(5) . . .
C111 O38 3.547(5) . . .
N112 C44 3.513(3) . 1_455 .
N112 N212 3.219(3) . 1_455 .
N112 O39 3.633(3) . 1_445 .
N112 C310 3.582(4) . 1_445 .
N112 C45 3.571(3) . 1_455 .
C22 O49 3.496(3) . . .
C22 C410 3.504(4) . . .
C23 C47 3.527(3) . . .
C23 O49 3.504(3) . . .
C24 N312 3.481(2) . 1_655 .
C25 O28 3.423(3) . 1_655 .
C26 C43 3.394(3) . 1_565 .
O28 N212 2.941(3) . 1_455 .
O28 N312 3.979(4) . . .
N212 N312 3.196(3) . 1_655 .
C34 N412 3.438(3) . 1_465 .
C35 O38 3.432(3) . 1_455 .
O38 N312 2.962(3) . 1_655 .
O38 C43 3.573(3) . 1_565 .
N312 N412 3.124(3) . 1_465 .
C45 O48 3.414(3) . 1_655 .
O48 N412 2.943(3) . 1_455 .
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
N112 H2N112 O18 1_455 1.00 1.98 2.941(3) 161.1 .
N212 H2N212 O28 1_655 1.00 1.99 2.941(3) 157.9 .
N312 H2N312 O38 1_455 1.00 2.04 2.962(3) 153.1 .
N412 H2N412 O48 1_655 1.00 1.99 2.943(3) 158.1 .
N112 H1N112 N412 1_455 1.00 3.25 4.094(3) 142.9 .
N212 H1N212 N112 1_655 1.00 2.22 3.219(3) 175.9 .
N312 H1N312 N212 1_455 1.00 2.20 3.196(3) 174.2 .
N412 H1N412 N312 1_645 1.00 2.13 3.124(3) 170.1 .
N112 H1N112 C44 1_455 1.00 2.56 3.513(3) 160.3 .
N212 H1N212 C14 1_655 1.00 2.48 3.382(3) 150.5 .
N312 H1N312 C24 1_455 1.00 2.63 3.481(2) 142.8 .
N412 H1N412 C34 1_645 1.00 2.61 3.438(3) 140.5 .
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
C16 C11 C12 C13 . . . . 0.0 .
C17 C11 C12 C13 . . . . 180.0 .
C12 C11 C16 C15 . . . . 0.0 .
C17 C11 C16 C15 . . . . -180.0 .
C12 C11 C17 O18 . . . . -1.0(2) .
C12 C11 C17 O19 . . . . -177.8(2) .
C16 C11 C17 O18 . . . . 179.0(2) .
C16 C11 C17 O19 . . . . 2.2(2) .
C11 C12 C13 C14 . . . . 0.0 .
C12 C13 C14 C15 . . . . 0.0 .
C12 C13 C14 N112 . . . . 180.0 .
C13 C14 C15 C16 . . . . 0.0 .
N112 C14 C15 C16 . . . . -180.0 .
C14 C15 C16 C11 . . . . 0.0 .
C11 C17 O19 C110 . . . . 179.4(2) .
O18 C17 O19 C110 . . . . 2.5(4) .
C17 O19 C110 C111 . . . . -175.1(3) .
C26 C21 C22 C23 . . . . 0.0 .
C27 C21 C22 C23 . . . . 180.0 .
C22 C21 C26 C25 . . . . 0.0 .
C27 C21 C26 C25 . . . . -180.0 .
C22 C21 C27 O28 . . . . -4.2(2) .
C22 C21 C27 O29 . . . . 179.6(2) .
C26 C21 C27 O28 . . . . 175.8(2) .
C26 C21 C27 O29 . . . . -0.4(2) .
C21 C22 C23 C24 . . . . 0.0 .
C22 C23 C24 C25 . . . . 0.0 .
C22 C23 C24 N212 . . . . -180.0 .
C23 C24 C25 C26 . . . . 0.0 .
N212 C24 C25 C26 . . . . 180.0 .
C24 C25 C26 C21 . . . . 0.0 .
C21 C27 O29 C210 . . . . 179.3(2) .
O28 C27 O29 C210 . . . . 3.0(4) .
C27 O29 C210 C211 . . . . 179.4(3) .
C36 C31 C32 C33 . . . . 0.0 .
C37 C31 C32 C33 . . . . 180.0 .
C32 C31 C36 C35 . . . . 0.0 .
C37 C31 C36 C35 . . . . -180.0 .
C32 C31 C37 O38 . . . . 2.6(2) .
C32 C31 C37 O39 . . . . -170.2(2) .
C36 C31 C37 O38 . . . . -177.4(2) .
C36 C31 C37 O39 . . . . 9.8(2) .
C31 C32 C33 C34 . . . . 0.0 .
C32 C33 C34 C35 . . . . 0.0 .
C32 C33 C34 N312 . . . . 180.0 .
C33 C34 C35 C36 . . . . 0.0 .
N312 C34 C35 C36 . . . . -180.0 .
C34 C35 C36 C31 . . . . 0.0 .
C31 C37 O39 C310 . . . . 176.7(2) .
O38 C37 O39 C310 . . . . 3.5(4) .
C37 O39 C310 C311 . . . . 173.5(3) .
C46 C41 C42 C43 . . . . 0.0 .
C47 C41 C42 C43 . . . . -180.0 .
C42 C41 C46 C45 . . . . 0.0 .
C47 C41 C46 C45 . . . . -180.0 .
C42 C41 C47 O48 . . . . 4.1(3) .
C42 C41 C47 O49 . . . . -161.6(2) .
C46 C41 C47 O48 . . . . -175.9(3) .
C46 C41 C47 O49 . . . . 18.4(2) .
C41 C42 C43 C44 . . . . 0.0 .
C42 C43 C44 C45 . . . . 0.0 .
C42 C43 C44 N412 . . . . -180.0 .
C43 C44 C45 C46 . . . . 0.0 .
N412 C44 C45 C46 . . . . -180.0 .
C44 C45 C46 C41 . . . . 0.0 .
C41 C47 O49 C410 . . . . 174.2(2) .
O48 C47 O49 C410 . . . . 7.9(4) .
C47 O49 C410 C411 . . . . 173.3(3) .
