#------------------------------------------------------------------------------
#$Date: 2023-05-06 13:48:33 +0300 (Sat, 06 May 2023) $
#$Revision: 283594 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/42/2244236.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_2244236
loop_
_publ_author_name
'Laban, Uroš'
'Naeem, Marilyn'
'Chadeayne, Andrew R.'
'Golen, James A.'
'Manke, David R.'
_publ_section_title
;
 Synthesis and structure of 4-hy-droxy-N-iso-propyl-tryptamine
 (4-HO-NiPT) and its precursors.
;
_journal_coeditor_code           HB8057
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              280
_journal_page_last               286
_journal_paper_doi               10.1107/S2056989023002098
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C20 H20 N2 O3'
_chemical_formula_moiety         'C20 H20 N2 O3'
_chemical_formula_sum            'C20 H20 N2 O3'
_chemical_formula_weight         336.38
_chemical_name_common
;
N-Isopropyl-4-benzyloxy-3-indoleglyoxylamide
;
_chemical_name_systematic
;
2-[4-(Benzyloxy)-1H-indol-3-yl]-2-oxo-N-(propan-2-yl)acetamide
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.4230(13)
_cell_length_b                   6.5609(4)
_cell_length_c                   33.469(2)
_cell_measurement_reflns_used    9851
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      23.92
_cell_measurement_theta_min      2.55
_cell_volume                     3606.3(4)
_computing_cell_refinement
;
SAINT (Bruker, 2021)
;
_computing_data_collection
;
APEX4 (Bruker, 2021)
;
_computing_data_reduction
;
SAINT (Bruker, 2021)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      300.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            48212
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         2.554
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2021)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.152
_refine_ls_abs_structure_details
;
 Refined as an inversion twin
;
_refine_ls_abs_structure_Flack   0.1(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     468
_refine_ls_number_reflns         6584
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0416P)²+1.3827P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1172
_reflns_number_gt                5295
_reflns_number_total             6584
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb8057sup1.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 2244235--2244238.cif.'
_cod_original_cell_volume        3606.2(4)
_cod_database_code               2244236
_cod_database_fobs_code          2244236
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_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'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.5240(2) 0.4291(5) 0.63818(8) 0.0793(10) Uani d 1 . .
O O2 0.4162(2) 0.2561(6) 0.55613(9) 0.0768(10) Uani d 1 . .
O O3 0.58588(18) 0.8372(5) 0.63145(7) 0.0597(8) Uani d 1 . .
N N1 0.6357(2) 0.4857(7) 0.51462(11) 0.0679(11) Uani d 1 . .
H H1 0.654322 0.447962 0.491765 0.081 Uiso calc 1 . .
N N2 0.4109(2) 0.1572(6) 0.62014(11) 0.0657(10) Uani d 1 . .
C C1 0.5799(3) 0.3846(8) 0.53570(13) 0.0636(11) Uani d 1 . .
H H1A 0.554698 0.264721 0.527535 0.076 Uiso calc 1 . .
C C2 0.6597(3) 0.6615(8) 0.53495(12) 0.0589(11) Uani d 1 . .
C C3 0.7126(3) 0.8123(10) 0.52259(15) 0.0748(15) Uani d 1 . .
H H3 0.739396 0.805187 0.498151 0.090 Uiso calc 1 . .
C C4 0.7236(3) 0.9720(9) 0.54802(14) 0.0741(14) Uani d 1 . .
H H4 0.758745 1.076869 0.540825 0.089 Uiso calc 1 . .
C C5 0.6830(3) 0.9818(8) 0.58479(12) 0.0612(11) Uani d 1 . .
H H5 0.692192 1.092406 0.601560 0.073 Uiso calc 1 . .
C C6 0.6296(2) 0.8310(6) 0.59669(11) 0.0492(10) Uani d 1 . .
C C7 0.6170(2) 0.6621(6) 0.57142(11) 0.0487(9) Uani d 1 . .
C C8 0.5648(3) 0.4837(6) 0.57149(11) 0.0502(9) Uani d 1 . .
C C9 0.5135(3) 0.4002(6) 0.60271(11) 0.0523(10) Uani d 1 . .
C C10 0.4423(3) 0.2625(6) 0.59046(12) 0.0538(10) Uani d 1 . .
C C11 0.3443(3) 0.0112(7) 0.61586(14) 0.0683(12) Uani d 1 . .
H H11 0.310596 0.052903 0.593100 0.082 Uiso calc 1 . .
C C12 0.2927(4) 0.0139(12) 0.6525(2) 0.120(3) Uani d 1 . .
H H12A 0.246303 -0.072908 0.648646 0.180 Uiso calc 1 . .
H H12B 0.274682 0.150566 0.657642 0.180 Uiso calc 1 . .
H H12C 0.323935 -0.034373 0.674832 0.180 Uiso calc 1 . .
C C13 0.3778(4) -0.1934(10) 0.6075(3) 0.137(3) Uani d 1 . .
H H13A 0.333875 -0.287603 0.603218 0.205 Uiso calc 1 . .
H H13B 0.409957 -0.237864 0.629772 0.205 Uiso calc 1 . .
H H13C 0.411226 -0.187746 0.583979 0.205 Uiso calc 1 . .
C C14 0.6120(3) 0.9724(7) 0.66161(12) 0.0606(11) Uani d 1 . .
H H14A 0.611897 1.110978 0.651536 0.073 Uiso calc 1 . .
H H14B 0.667060 0.938485 0.669739 0.073 Uiso calc 1 . .
C C15 0.5556(3) 0.9555(7) 0.69666(12) 0.0569(10) Uani d 1 . .
C C16 0.5345(3) 1.1282(8) 0.71718(14) 0.0739(13) Uani d 1 . .
H H16 0.554437 1.254255 0.709074 0.089 Uiso calc 1 . .
C C17 0.4829(4) 1.1146(11) 0.75046(16) 0.0929(19) Uani d 1 . .
H H17 0.468398 1.231677 0.764431 0.112 Uiso calc 1 . .
C C18 0.4540(4) 0.9305(12) 0.76219(16) 0.0919(18) Uani d 1 . .
H H18 0.420685 0.921799 0.784579 0.110 Uiso calc 1 . .
C C19 0.4728(4) 0.7627(11) 0.74217(16) 0.0945(19) Uani d 1 . .
H H19 0.452191 0.637347 0.750308 0.113 Uiso calc 1 . .
C C20 0.5232(4) 0.7744(9) 0.70914(17) 0.0851(16) Uani d 1 . .
H H20 0.535284 0.656109 0.695042 0.102 Uiso calc 1 . .
O O4 0.2897(2) 0.4332(5) 0.36366(8) 0.0784(10) Uani d 1 . .
O O5 0.1974(2) 0.2158(6) 0.44698(10) 0.0901(11) Uani d 1 . .
O O6 0.35700(18) 0.8328(5) 0.36871(8) 0.0625(8) Uani d 1 . .
N N3 0.4045(3) 0.4959(7) 0.48712(12) 0.0727(12) Uani d 1 . .
N N4 0.1780(3) 0.1631(6) 0.38136(12) 0.0727(11) Uani d 1 . .
C C21 0.3495(3) 0.3903(8) 0.46630(13) 0.0644(12) Uani d 1 . .
H H21 0.324853 0.270395 0.474817 0.077 Uiso calc 1 . .
C C22 0.4279(3) 0.6671(8) 0.46657(13) 0.0617(12) Uani d 1 . .
C C23 0.4817(3) 0.8206(10) 0.47795(14) 0.0741(14) Uani d 1 . .
H H23 0.507633 0.817635 0.502655 0.089 Uiso calc 1 . .
C C24 0.4950(3) 0.9755(9) 0.45151(15) 0.0779(14) Uani d 1 . .
H H24 0.531739 1.078188 0.458057 0.093 Uiso calc 1 . .
C C25 0.4543(3) 0.9828(8) 0.41458(13) 0.0658(12) Uani d 1 . .
H H25 0.464119 1.090643 0.397189 0.079 Uiso calc 1 . .
C C26 0.4000(3) 0.8317(7) 0.40384(12) 0.0537(10) Uani d 1 . .
C C27 0.3857(2) 0.6662(7) 0.42979(11) 0.0521(10) Uani d 1 . .
C C28 0.3347(3) 0.4858(7) 0.43015(11) 0.0557(11) Uani d 1 . .
C C29 0.2838(3) 0.3987(7) 0.39941(12) 0.0602(11) Uani d 1 . .
C C30 0.2157(3) 0.2463(7) 0.41220(13) 0.0630(12) Uani d 1 . .
C C31 0.1127(3) 0.0105(8) 0.38476(16) 0.0762(14) Uani d 1 . .
H H31 0.079731 0.044781 0.408215 0.091 Uiso calc 1 . .
C C32 0.1477(4) -0.1950(10) 0.3911(3) 0.132(3) Uani d 1 . .
H H32A 0.105164 -0.288177 0.398326 0.198 Uiso calc 1 . .
H H32B 0.187428 -0.189390 0.412091 0.198 Uiso calc 1 . .
H H32C 0.173287 -0.240602 0.366869 0.198 Uiso calc 1 . .
C C33 0.0584(4) 0.0240(12) 0.3481(2) 0.118(2) Uani d 1 . .
H H33A 0.014535 -0.071859 0.350550 0.176 Uiso calc 1 . .
H H33B 0.089728 -0.007008 0.324646 0.176 Uiso calc 1 . .
H H33C 0.036669 0.159366 0.345916 0.176 Uiso calc 1 . .
C C34 0.3794(3) 0.9784(7) 0.33933(13) 0.0627(11) Uani d 1 . .
H H34A 0.435266 0.955549 0.331010 0.075 Uiso calc 1 . .
H H34B 0.375553 1.114783 0.350360 0.075 Uiso calc 1 . .
C C35 0.3235(3) 0.9582(7) 0.30415(12) 0.0569(10) Uani d 1 . .
C C36 0.2928(4) 0.7746(8) 0.29169(16) 0.0822(16) Uani d 1 . .
H H36 0.305948 0.656060 0.305515 0.099 Uiso calc 1 . .
C C37 0.2430(4) 0.7651(11) 0.25894(19) 0.102(2) Uani d 1 . .
H H37 0.223112 0.639073 0.250766 0.122 Uiso calc 1 . .
C C38 0.2219(4) 0.9337(13) 0.23815(16) 0.0936(19) Uani d 1 . .
H H38 0.188330 0.924009 0.215841 0.112 Uiso calc 1 . .
C C39 0.2504(4) 1.1171(10) 0.25040(16) 0.0881(17) Uani d 1 . .
H H39 0.235846 1.234867 0.236685 0.106 Uiso calc 1 . .
C C40 0.3017(3) 1.1296(8) 0.28350(14) 0.0709(13) Uani d 1 . .
H H40 0.321249 1.255985 0.291639 0.085 Uiso calc 1 . .
H H2 0.433(2) 0.187(7) 0.6439(7) 0.057(12) Uiso d 1 . .
H H4A 0.199(3) 0.184(8) 0.3569(8) 0.091(17) Uiso d 1 . .
H H3A 0.420(3) 0.448(7) 0.5101(8) 0.086(16) Uiso d 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
C6 O3 C14 . . 117.9(3) ?
C1 N1 H1 . . 124.9 ?
C1 N1 C2 . . 110.3(4) ?
C2 N1 H1 . . 124.9 ?
C10 N2 C11 . . 124.3(4) ?
C10 N2 H2 . . 113(3) ?
C11 N2 H2 . . 122(3) ?
N1 C1 H1A . . 124.8 ?
N1 C1 C8 . . 110.3(4) ?
C8 C1 H1A . . 124.8 ?
N1 C2 C7 . . 106.6(4) ?
C3 C2 N1 . . 128.6(4) ?
C3 C2 C7 . . 124.8(5) ?
C2 C3 H3 . . 121.7 ?
C4 C3 C2 . . 116.6(4) ?
C4 C3 H3 . . 121.7 ?
C3 C4 H4 . . 119.3 ?
C3 C4 C5 . . 121.4(5) ?
C5 C4 H4 . . 119.3 ?
C4 C5 H5 . . 119.2 ?
C6 C5 C4 . . 121.5(4) ?
C6 C5 H5 . . 119.2 ?
O3 C6 C5 . . 123.9(4) ?
O3 C6 C7 . . 117.1(4) ?
C5 C6 C7 . . 118.9(4) ?
C2 C7 C6 . . 116.7(4) ?
C2 C7 C8 . . 107.0(4) ?
C6 C7 C8 . . 136.1(3) ?
C1 C8 C7 . . 105.8(4) ?
C1 C8 C9 . . 123.4(4) ?
C9 C8 C7 . . 130.5(3) ?
O1 C9 C8 . . 124.3(4) ?
O1 C9 C10 . . 117.5(4) ?
C8 C9 C10 . . 118.2(3) ?
O2 C10 N2 . . 123.5(4) ?
O2 C10 C9 . . 122.5(4) ?
N2 C10 C9 . . 114.0(4) ?
N2 C11 H11 . . 108.4 ?
N2 C11 C12 . . 109.7(4) ?
N2 C11 C13 . . 109.6(4) ?
C12 C11 H11 . . 108.4 ?
C13 C11 H11 . . 108.4 ?
C13 C11 C12 . . 112.2(6) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12B . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13B . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
O3 C14 H14A . . 109.9 ?
O3 C14 H14B . . 109.9 ?
O3 C14 C15 . . 109.0(3) ?
H14A C14 H14B . . 108.3 ?
C15 C14 H14A . . 109.9 ?
C15 C14 H14B . . 109.9 ?
C16 C15 C14 . . 119.2(4) ?
C20 C15 C14 . . 122.9(4) ?
C20 C15 C16 . . 117.9(4) ?
C15 C16 H16 . . 120.1 ?
C15 C16 C17 . . 119.9(5) ?
C17 C16 H16 . . 120.1 ?
C16 C17 H17 . . 120.1 ?
C18 C17 C16 . . 119.8(5) ?
C18 C17 H17 . . 120.1 ?
C17 C18 H18 . . 119.6 ?
C19 C18 C17 . . 120.8(5) ?
C19 C18 H18 . . 119.6 ?
C18 C19 H19 . . 120.1 ?
C18 C19 C20 . . 119.8(6) ?
C20 C19 H19 . . 120.1 ?
C15 C20 C19 . . 121.7(5) ?
C15 C20 H20 . . 119.1 ?
C19 C20 H20 . . 119.1 ?
C26 O6 C34 . . 117.6(3) ?
C21 N3 C22 . . 110.6(4) ?
C21 N3 H3A . . 119(3) ?
C22 N3 H3A . . 131(3) ?
C30 N4 C31 . . 124.2(4) ?
C30 N4 H4A . . 118(4) ?
C31 N4 H4A . . 117(4) ?
N3 C21 H21 . . 125.0 ?
N3 C21 C28 . . 109.9(5) ?
C28 C21 H21 . . 125.0 ?
N3 C22 C23 . . 129.2(5) ?
N3 C22 C27 . . 107.2(4) ?
C23 C22 C27 . . 123.5(4) ?
C22 C23 H23 . . 121.2 ?
C24 C23 C22 . . 117.5(4) ?
C24 C23 H23 . . 121.2 ?
C23 C24 H24 . . 119.4 ?
C23 C24 C25 . . 121.3(5) ?
C25 C24 H24 . . 119.4 ?
C24 C25 H25 . . 119.6 ?
C26 C25 C24 . . 120.8(5) ?
C26 C25 H25 . . 119.6 ?
O6 C26 C25 . . 123.5(4) ?
O6 C26 C27 . . 116.5(4) ?
C25 C26 C27 . . 120.0(4) ?
C22 C27 C28 . . 106.2(4) ?
C26 C27 C22 . . 116.9(4) ?
C26 C27 C28 . . 136.9(4) ?
C21 C28 C27 . . 106.0(4) ?
C21 C28 C29 . . 123.1(4) ?
C29 C28 C27 . . 130.7(4) ?
O4 C29 C28 . . 125.4(4) ?
O4 C29 C30 . . 116.4(4) ?
C28 C29 C30 . . 118.3(3) ?
O5 C30 N4 . . 124.2(5) ?
O5 C30 C29 . . 123.0(4) ?
N4 C30 C29 . . 112.7(4) ?
N4 C31 H31 . . 108.0 ?
N4 C31 C32 . . 110.3(5) ?
N4 C31 C33 . . 109.0(4) ?
C32 C31 H31 . . 108.0 ?
C32 C31 C33 . . 113.3(6) ?
C33 C31 H31 . . 108.0 ?
C31 C32 H32A . . 109.5 ?
C31 C32 H32B . . 109.5 ?
C31 C32 H32C . . 109.5 ?
H32A C32 H32B . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
C31 C33 H33A . . 109.5 ?
C31 C33 H33B . . 109.5 ?
C31 C33 H33C . . 109.5 ?
H33A C33 H33B . . 109.5 ?
H33A C33 H33C . . 109.5 ?
H33B C33 H33C . . 109.5 ?
O6 C34 H34A . . 109.9 ?
O6 C34 H34B . . 109.9 ?
O6 C34 C35 . . 109.0(3) ?
H34A C34 H34B . . 108.3 ?
C35 C34 H34A . . 109.9 ?
C35 C34 H34B . . 109.9 ?
C36 C35 C34 . . 122.8(4) ?
C40 C35 C34 . . 119.0(4) ?
C40 C35 C36 . . 118.2(4) ?
C35 C36 H36 . . 119.9 ?
C37 C36 C35 . . 120.2(5) ?
C37 C36 H36 . . 119.9 ?
C36 C37 H37 . . 119.1 ?
C38 C37 C36 . . 121.9(6) ?
C38 C37 H37 . . 119.1 ?
C37 C38 H38 . . 120.6 ?
C37 C38 C39 . . 118.8(5) ?
C39 C38 H38 . . 120.6 ?
C38 C39 H39 . . 119.9 ?
C38 C39 C40 . . 120.1(5) ?
C40 C39 H39 . . 119.9 ?
C35 C40 C39 . . 120.8(5) ?
C35 C40 H40 . . 119.6 ?
C39 C40 H40 . . 119.6 ?
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 C9 . 1.215(4) ?
O2 C10 . 1.227(5) ?
O3 C6 . 1.368(4) ?
O3 C14 . 1.411(5) ?
N1 H1 . 0.8600 ?
N1 C1 . 1.333(6) ?
N1 C2 . 1.396(6) ?
N2 C10 . 1.315(5) ?
N2 C11 . 1.461(6) ?
N2 H2 . 0.894(14) ?
C1 H1A . 0.9300 ?
C1 C8 . 1.385(6) ?
C2 C3 . 1.381(7) ?
C2 C7 . 1.408(5) ?
C3 H3 . 0.9300 ?
C3 C4 . 1.362(8) ?
C4 H4 . 0.9300 ?
C4 C5 . 1.401(6) ?
C5 H5 . 0.9300 ?
C5 C6 . 1.380(6) ?
C6 C7 . 1.410(6) ?
C7 C8 . 1.451(6) ?
C8 C9 . 1.450(6) ?
C9 C10 . 1.533(6) ?
C11 H11 . 0.9800 ?
C11 C12 . 1.491(8) ?
C11 C13 . 1.478(8) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C14 C15 . 1.499(6) ?
C15 C16 . 1.369(7) ?
C15 C20 . 1.367(7) ?
C16 H16 . 0.9300 ?
C16 C17 . 1.403(8) ?
C17 H17 . 0.9300 ?
C17 C18 . 1.356(9) ?
C18 H18 . 0.9300 ?
C18 C19 . 1.325(9) ?
C19 H19 . 0.9300 ?
C19 C20 . 1.382(8) ?
C20 H20 . 0.9300 ?
O4 C29 . 1.222(5) ?
O5 C30 . 1.219(5) ?
O6 C26 . 1.372(5) ?
O6 C34 . 1.420(5) ?
N3 C21 . 1.334(6) ?
N3 C22 . 1.372(7) ?
N3 H3A . 0.871(15) ?
N4 C30 . 1.322(6) ?
N4 C31 . 1.471(6) ?
N4 H4A . 0.897(15) ?
C21 H21 . 0.9300 ?
C21 C28 . 1.384(6) ?
C22 C23 . 1.394(8) ?
C22 C27 . 1.412(6) ?
C23 H23 . 0.9300 ?
C23 C24 . 1.365(8) ?
C24 H24 . 0.9300 ?
C24 C25 . 1.406(6) ?
C25 H25 . 0.9300 ?
C25 C26 . 1.381(7) ?
C26 C27 . 1.410(6) ?
C27 C28 . 1.450(6) ?
C28 C29 . 1.444(6) ?
C29 C30 . 1.560(6) ?
C31 H31 . 0.9800 ?
C31 C32 . 1.481(8) ?
C31 C33 . 1.520(8) ?
C32 H32A . 0.9600 ?
C32 H32B . 0.9600 ?
C32 H32C . 0.9600 ?
C33 H33A . 0.9600 ?
C33 H33B . 0.9600 ?
C33 H33C . 0.9600 ?
C34 H34A . 0.9700 ?
C34 H34B . 0.9700 ?
C34 C35 . 1.499(6) ?
C35 C36 . 1.371(7) ?
C35 C40 . 1.368(6) ?
C36 H36 . 0.9300 ?
C36 C37 . 1.369(8) ?
C37 H37 . 0.9300 ?
C37 C38 . 1.352(9) ?
C38 H38 . 0.9300 ?
C38 C39 . 1.355(9) ?
C39 H39 . 0.9300 ?
C39 C40 . 1.393(7) ?
C40 H40 . 0.9300 ?
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
N1 H1 O5 3 0.86 1.98 2.810(5) 164 yes
N3 H3A O2 . 0.871(15) 1.99(3) 2.801(5) 154(5) 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
O1 C9 C10 O2 . . . . 164.9(5) ?
O1 C9 C10 N2 . . . . -13.5(6) ?
O3 C6 C7 C2 . . . . 177.4(3) ?
O3 C6 C7 C8 . . . . 2.7(7) ?
O3 C14 C15 C16 . . . . -141.2(4) ?
O3 C14 C15 C20 . . . . 38.2(6) ?
N1 C1 C8 C7 . . . . 0.2(5) ?
N1 C1 C8 C9 . . . . -173.3(4) ?
N1 C2 C3 C4 . . . . 178.1(5) ?
N1 C2 C7 C6 . . . . -178.0(3) ?
N1 C2 C7 C8 . . . . -1.8(4) ?
C1 N1 C2 C3 . . . . -176.3(5) ?
C1 N1 C2 C7 . . . . 2.0(5) ?
C1 C8 C9 O1 . . . . 147.7(5) ?
C1 C8 C9 C10 . . . . -30.9(6) ?
C2 N1 C1 C8 . . . . -1.4(5) ?
C2 C3 C4 C5 . . . . 0.0(8) ?
C2 C7 C8 C1 . . . . 1.0(4) ?
C2 C7 C8 C9 . . . . 173.9(4) ?
C3 C2 C7 C6 . . . . 0.4(6) ?
C3 C2 C7 C8 . . . . 176.6(4) ?
C3 C4 C5 C6 . . . . -0.6(8) ?
C4 C5 C6 O3 . . . . -177.2(4) ?
C4 C5 C6 C7 . . . . 1.1(6) ?
C5 C6 C7 C2 . . . . -1.0(5) ?
C5 C6 C7 C8 . . . . -175.7(4) ?
C6 O3 C14 C15 . . . . 179.6(4) ?
C6 C7 C8 C1 . . . . 176.1(4) ?
C6 C7 C8 C9 . . . . -11.0(8) ?
C7 C2 C3 C4 . . . . 0.1(7) ?
C7 C8 C9 O1 . . . . -24.1(7) ?
C7 C8 C9 C10 . . . . 157.3(4) ?
C8 C9 C10 O2 . . . . -16.4(6) ?
C8 C9 C10 N2 . . . . 165.2(4) ?
C10 N2 C11 C12 . . . . -146.4(5) ?
C10 N2 C11 C13 . . . . 90.0(6) ?
C11 N2 C10 O2 . . . . 3.5(7) ?
C11 N2 C10 C9 . . . . -178.1(4) ?
C14 O3 C6 C5 . . . . -18.0(6) ?
C14 O3 C6 C7 . . . . 163.8(4) ?
C14 C15 C16 C17 . . . . -178.9(4) ?
C14 C15 C20 C19 . . . . 178.4(5) ?
C15 C16 C17 C18 . . . . 0.1(8) ?
C16 C15 C20 C19 . . . . -2.1(8) ?
C16 C17 C18 C19 . . . . -1.3(9) ?
C17 C18 C19 C20 . . . . 0.7(10) ?
C18 C19 C20 C15 . . . . 1.0(10) ?
C20 C15 C16 C17 . . . . 1.6(7) ?
O4 C29 C30 O5 . . . . -171.7(5) ?
O4 C29 C30 N4 . . . . 5.2(6) ?
O6 C26 C27 C22 . . . . -178.1(3) ?
O6 C26 C27 C28 . . . . -0.7(7) ?
O6 C34 C35 C36 . . . . -34.8(6) ?
O6 C34 C35 C40 . . . . 145.0(4) ?
N3 C21 C28 C27 . . . . -0.4(5) ?
N3 C21 C28 C29 . . . . 174.1(4) ?
N3 C22 C23 C24 . . . . 179.5(5) ?
N3 C22 C27 C26 . . . . 179.2(4) ?
N3 C22 C27 C28 . . . . 1.0(4) ?
C21 N3 C22 C23 . . . . 178.0(5) ?
C21 N3 C22 C27 . . . . -1.3(5) ?
C21 C28 C29 O4 . . . . -153.3(5) ?
C21 C28 C29 C30 . . . . 26.2(6) ?
C22 N3 C21 C28 . . . . 1.1(5) ?
C22 C23 C24 C25 . . . . 1.6(8) ?
C22 C27 C28 C21 . . . . -0.4(4) ?
C22 C27 C28 C29 . . . . -174.3(4) ?
C23 C22 C27 C26 . . . . -0.1(6) ?
C23 C22 C27 C28 . . . . -178.3(4) ?
C23 C24 C25 C26 . . . . -0.6(8) ?
C24 C25 C26 O6 . . . . 178.4(4) ?
C24 C25 C26 C27 . . . . -0.9(7) ?
C25 C26 C27 C22 . . . . 1.2(6) ?
C25 C26 C27 C28 . . . . 178.6(4) ?
C26 O6 C34 C35 . . . . -178.2(4) ?
C26 C27 C28 C21 . . . . -178.0(5) ?
C26 C27 C28 C29 . . . . 8.1(8) ?
C27 C22 C23 C24 . . . . -1.3(7) ?
C27 C28 C29 O4 . . . . 19.7(7) ?
C27 C28 C29 C30 . . . . -160.8(4) ?
C28 C29 C30 O5 . . . . 8.8(6) ?
C28 C29 C30 N4 . . . . -174.3(4) ?
C30 N4 C31 C32 . . . . -81.7(7) ?
C30 N4 C31 C33 . . . . 153.3(5) ?
C31 N4 C30 O5 . . . . -4.7(8) ?
C31 N4 C30 C29 . . . . 178.5(4) ?
C34 O6 C26 C25 . . . . 10.6(6) ?
C34 O6 C26 C27 . . . . -170.1(4) ?
C34 C35 C36 C37 . . . . -179.0(5) ?
C34 C35 C40 C39 . . . . 179.4(4) ?
C35 C36 C37 C38 . . . . -0.5(10) ?
C36 C35 C40 C39 . . . . -0.8(7) ?
C36 C37 C38 C39 . . . . -0.6(10) ?
C37 C38 C39 C40 . . . . 1.0(9) ?
C38 C39 C40 C35 . . . . -0.3(8) ?
C40 C35 C36 C37 . . . . 1.2(8) ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9(18)
2 0.1(18)
