#------------------------------------------------------------------------------
#$Date: 2022-03-02 05:03:36 +0200 (Wed, 02 Mar 2022) $
#$Revision: 273203 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/40/2244043.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_2244043
loop_
_publ_author_name
'Yennawar, Hemant P.'
'Sigmon, Anna'
_publ_section_title
;
 Crystal structure of racemic
 (R/S,E)-2-(4-hydroxyphenyl)-4-(2-phenylhydrazin-1-ylidene)chromane-5,7-diol
 ethanol monosolvate
;
_journal_coeditor_code           JY2016
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022002079
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C21 H18 N2 O4, C2 H6 O'
_chemical_formula_moiety         'C21 H18 N2 O4, C2 H6 O'
_chemical_formula_sum            'C23 H24 N2 O5'
_chemical_formula_weight         408.44
_chemical_name_systematic
'(R/S,E)-2-(4-Hydroxyphenyl)-4-(2-phenylhydrazin-1-ylidene)chromane-5,7-diol ethanol monosolvate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_cell_angle_alpha                115.244(3)
_cell_angle_beta                 93.939(2)
_cell_angle_gamma                104.180(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4329(3)
_cell_length_b                   10.9974(4)
_cell_length_c                   11.9310(3)
_cell_measurement_reflns_used    8481
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4320
_cell_measurement_theta_min      4.1140
_cell_volume                     1064.01(7)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku Oxford Diffraction, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14477
_diffrn_reflns_theta_full        66.968
_diffrn_reflns_theta_max         74.019
_diffrn_reflns_theta_min         4.179
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.173
_refine_ls_extinction_coef       0.0070(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018/3 (Sheldrick 2015b)
;
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         4067
_refine_ls_number_restraints     183
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0490
_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)+(0.0996P)²+0.0482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.1605
_reflns_number_gt                3077
_reflns_number_total             4067
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jy2016sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1064.01(6)
_cod_database_code               2244043
_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   0.866
_shelx_estimated_absorpt_t_max   0.910
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.63930(15) 0.57227(12) 0.15536(11) 0.0762(4) Uani d 1 . .
H H1 0.702063 0.648464 0.176530 0.114 Uiso calc 1 . .
O O2 0.23838(15) 0.35612(12) 0.28729(11) 0.0818(4) Uani d 1 . .
H H2 0.203745 0.365438 0.350612 0.123 Uiso calc 1 . .
O O3 0.56642(13) 0.82028(11) 0.57204(10) 0.0708(4) Uani d 1 . .
N N1 0.20641(15) 0.48554(13) 0.51936(12) 0.0602(3) Uani d 1 . .
N N2 0.12754(15) 0.49326(14) 0.61217(12) 0.0680(4) Uani d 1 . .
H H2A 0.142115 0.572868 0.677760 0.082 Uiso calc 1 . .
C C1 0.56086(19) 0.58198(16) 0.24987(14) 0.0620(4) Uani d 1 . .
C C2 0.43809(19) 0.46783(16) 0.22400(15) 0.0661(4) Uani d 1 . .
H H2B 0.410135 0.389868 0.144550 0.079 Uiso calc 1 . .
C C3 0.35768(19) 0.47058(16) 0.31680(15) 0.0624(4) Uani d 1 . .
C C4 0.39633(17) 0.58758(15) 0.43746(14) 0.0549(4) Uani d 1 . .
C C5 0.52020(17) 0.70112(15) 0.45827(14) 0.0566(4) Uani d 1 . .
C C6 0.60281(18) 0.69960(15) 0.36667(14) 0.0625(4) Uani d 1 . .
H H6 0.684912 0.776159 0.383312 0.075 Uiso calc 1 . .
C C7 0.31398(16) 0.59550(15) 0.53822(14) 0.0556(4) Uani d 1 . .
C C8 0.36188(19) 0.73182(16) 0.65742(15) 0.0638(4) Uani d 1 . .
H H8A 0.273783 0.754978 0.686079 0.077 Uiso calc 0.562(6) A 1
H H8B 0.415896 0.719516 0.722028 0.077 Uiso calc 0.562(6) A 1
H H8BC 0.346340 0.712882 0.728678 0.077 Uiso calc 0.438(6) A 2
H H8BD 0.300754 0.789928 0.654184 0.077 Uiso calc 0.438(6) A 2
C C16 0.02353(17) 0.37295(17) 0.60136(15) 0.0623(4) Uani d 1 . .
C C17 -0.0611(2) 0.3883(2) 0.69450(18) 0.0748(5) Uani d 1 . .
H H17 -0.046879 0.476957 0.761543 0.090 Uiso calc 1 . .
C C18 -0.1667(2) 0.2717(2) 0.6877(2) 0.0878(6) Uani d 1 . .
H H18 -0.223327 0.282924 0.750162 0.105 Uiso calc 1 . .
C C19 -0.1889(2) 0.1394(2) 0.5899(2) 0.0914(6) Uani d 1 . .
H H19 -0.259464 0.061386 0.586085 0.110 Uiso calc 1 . .
C C20 -0.1055(2) 0.1245(2) 0.4981(2) 0.0850(6) Uani d 1 . .
H H20 -0.120445 0.035349 0.431597 0.102 Uiso calc 1 . .
C C21 0.0010(2) 0.23960(18) 0.50212(17) 0.0721(5) Uani d 1 . .
H H21 0.056675 0.227415 0.438926 0.087 Uiso calc 1 . .
O O4A 0.7311(17) 1.3456(9) 1.1039(9) 0.081(3) Uani d 0.562(6) A 1
H H4A 0.703178 1.409645 1.101761 0.121 Uiso calc 0.562(6) A 1
C C9A 0.4577(4) 0.8518(3) 0.6438(3) 0.0590(10) Uani d 0.562(6) A 1
H H9A 0.391142 0.878767 0.598130 0.071 Uiso calc 0.562(6) A 1
C C10A 0.5317(5) 0.9817(5) 0.7668(4) 0.0543(10) Uani d 0.562(6) A 1
C C11A 0.6354(6) 0.9803(5) 0.8543(5) 0.0658(12) Uani d 0.562(6) A 1
H H11A 0.660538 0.898387 0.837484 0.079 Uiso calc 0.562(6) A 1
C C12A 0.7007(13) 1.1010(7) 0.9660(7) 0.0732(17) Uani d 0.562(6) A 1
H H12A 0.766711 1.098188 1.025843 0.088 Uiso calc 0.562(6) A 1
C C13A 0.671(2) 1.2248(10) 0.9914(13) 0.0566(18) Uani d 0.562(6) A 1
C C14A 0.5663(11) 1.2260(6) 0.9061(7) 0.0598(13) Uani d 0.562(6) A 1
H H14A 0.541170 1.308011 0.923497 0.072 Uiso calc 0.562(6) A 1
C C15A 0.4986(6) 1.1050(5) 0.7947(5) 0.0599(11) Uani d 0.562(6) A 1
H H15A 0.428862 1.107069 0.737042 0.072 Uiso calc 0.562(6) A 1
O O4B 0.751(2) 1.3415(10) 1.1041(12) 0.0660(19) Uani d 0.438(6) A 2
H H4B 0.811016 1.329869 1.148770 0.099 Uiso calc 0.438(6) A 2
C C9B 0.5225(5) 0.8106(4) 0.6767(3) 0.0556(12) Uani d 0.438(6) A 2
H H9B 0.579037 0.755148 0.694866 0.067 Uiso calc 0.438(6) A 2
C C10B 0.5752(7) 0.9547(5) 0.7898(5) 0.0511(12) Uani d 0.438(6) A 2
C C11B 0.6689(9) 0.9752(6) 0.8945(6) 0.0663(15) Uani d 0.438(6) A 2
H H11B 0.696726 0.899741 0.894502 0.080 Uiso calc 0.438(6) A 2
C C12B 0.7214(16) 1.1043(8) 0.9980(8) 0.0658(18) Uani d 0.438(6) A 2
H H12B 0.788594 1.117299 1.065956 0.079 Uiso calc 0.438(6) A 2
C C13B 0.676(3) 1.2142(13) 1.0021(16) 0.061(2) Uani d 0.438(6) A 2
C C14B 0.5818(16) 1.1960(9) 0.8993(10) 0.070(2) Uani d 0.438(6) A 2
H H14B 0.552914 1.271569 0.900630 0.084 Uiso calc 0.438(6) A 2
C C15B 0.5302(8) 1.0657(7) 0.7936(6) 0.0631(15) Uani d 0.438(6) A 2
H H15B 0.464655 1.053270 0.724979 0.076 Uiso calc 0.438(6) A 2
O O5A 0.1303(15) 0.2093(13) 0.7784(9) 0.115(3) Uani d 0.487(7) B 1
H H5A 0.070539 0.240431 0.754421 0.172 Uiso calc 0.487(7) B 1
C C22A 0.0763(14) 0.0563(13) 0.8743(13) 0.225(5) Uani d 0.487(7) B 1
H H22A 0.138147 0.010641 0.820731 0.338 Uiso calc 0.487(7) B 1
H H22B -0.022803 -0.007894 0.850552 0.338 Uiso calc 0.487(7) B 1
H H22C 0.116684 0.084083 0.960680 0.338 Uiso calc 0.487(7) B 1
C C23A 0.0723(17) 0.1585(15) 0.8628(12) 0.169(4) Uani d 0.487(7) B 1
H H23A 0.115468 0.236841 0.946343 0.203 Uiso calc 0.487(7) B 1
H H23B -0.032950 0.150256 0.849370 0.203 Uiso calc 0.487(7) B 1
O O5B 0.8710(12) 0.8064(8) 0.2186(6) 0.0826(19) Uani d 0.513(7) B 2
H H5B 0.951087 0.826239 0.263805 0.124 Uiso calc 0.513(7) B 2
C C22B 0.9159(9) 0.7123(10) 0.0163(6) 0.188(4) Uani d 0.513(7) B 2
H H22D 1.006501 0.697937 0.042231 0.282 Uiso calc 0.513(7) B 2
H H22E 0.922411 0.727388 -0.056931 0.282 Uiso calc 0.513(7) B 2
H H22F 0.833254 0.630478 -0.003716 0.282 Uiso calc 0.513(7) B 2
C C23B 0.8974(16) 0.8167(14) 0.1032(9) 0.170(5) Uani d 0.513(7) B 2
H H23C 0.813280 0.836918 0.071298 0.204 Uiso calc 0.513(7) B 2
H H23D 0.984834 0.896724 0.125438 0.204 Uiso calc 0.513(7) B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -2 2 0.0755
4 -4 -3 0.0896
-1 1 1 0.0871
1 -1 -1 0.0870
-5 -2 2 0.0999
3 2 3 0.0566
-1 1 5 0.0608
1 -1 -5 0.0670
4 3 1 0.0570
-2 -5 3 0.0992
0 4 3 0.0731
1 1 -5 0.0875
-3 5 -3 0.0983
0 -1 5 0.0656
-3 3 -5 0.0694
5 0 3 0.0567
2 0 1 0.0570
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
C1 O1 H1 . . 109.5 ?
C3 O2 H2 . . 109.5 ?
C5 O3 C9A . . 116.51(15) ?
C5 O3 C9B . . 117.93(16) ?
C7 N1 N2 . . 118.79(13) ?
N1 N2 H2A . . 119.9 ?
N1 N2 C16 . . 120.22(13) ?
C16 N2 H2A . . 119.9 ?
O1 C1 C2 . . 117.22(14) ?
O1 C1 C6 . . 121.70(14) ?
C6 C1 C2 . . 121.08(14) ?
C1 C2 H2B . . 120.2 ?
C3 C2 C1 . . 119.57(14) ?
C3 C2 H2B . . 120.2 ?
O2 C3 C2 . . 117.53(14) ?
O2 C3 C4 . . 120.95(14) ?
C2 C3 C4 . . 121.52(14) ?
C3 C4 C7 . . 123.41(13) ?
C5 C4 C3 . . 116.68(13) ?
C5 C4 C7 . . 119.91(13) ?
O3 C5 C4 . . 121.29(13) ?
O3 C5 C6 . . 116.16(13) ?
C6 C5 C4 . . 122.55(13) ?
C1 C6 C5 . . 118.60(14) ?
C1 C6 H6 . . 120.7 ?
C5 C6 H6 . . 120.7 ?
N1 C7 C4 . . 118.58(13) ?
N1 C7 C8 . . 124.66(14) ?
C4 C7 C8 . . 116.75(12) ?
C7 C8 H8A . . 108.8 ?
C7 C8 H8B . . 108.8 ?
C7 C8 H8BC . . 109.3 ?
C7 C8 H8BD . . 109.3 ?
C7 C8 C9B . . 111.81(17) ?
H8A C8 H8B . . 107.7 ?
H8BC C8 H8BD . . 107.9 ?
C9A C8 C7 . . 113.85(15) ?
C9A C8 H8A . . 108.8 ?
C9A C8 H8B . . 108.8 ?
C9B C8 H8BC . . 109.3 ?
C9B C8 H8BD . . 109.3 ?
C17 C16 N2 . . 117.90(15) ?
C17 C16 C21 . . 119.15(15) ?
C21 C16 N2 . . 122.94(15) ?
C16 C17 H17 . . 120.0 ?
C18 C17 C16 . . 120.09(18) ?
C18 C17 H17 . . 120.0 ?
C17 C18 H18 . . 119.5 ?
C19 C18 C17 . . 120.91(18) ?
C19 C18 H18 . . 119.5 ?
C18 C19 H19 . . 120.5 ?
C20 C19 C18 . . 118.93(17) ?
C20 C19 H19 . . 120.5 ?
C19 C20 H20 . . 119.2 ?
C19 C20 C21 . . 121.52(19) ?
C21 C20 H20 . . 119.2 ?
C16 C21 C20 . . 119.38(17) ?
C16 C21 H21 . . 120.3 ?
C20 C21 H21 . . 120.3 ?
C13A O4A H4A . . 109.5 ?
O3 C9A C8 . . 115.0(2) ?
O3 C9A H9A . . 106.1 ?
O3 C9A C10A . . 108.3(2) ?
C8 C9A H9A . . 106.1 ?
C8 C9A C10A . . 114.4(2) ?
C10A C9A H9A . . 106.1 ?
C11A C10A C9A . . 121.1(4) ?
C15A C10A C9A . . 120.5(4) ?
C15A C10A C11A . . 118.4(3) ?
C10A C11A H11A . . 120.2 ?
C12A C11A C10A . . 119.5(4) ?
C12A C11A H11A . . 120.2 ?
C11A C12A H12A . . 119.1 ?
C13A C12A C11A . . 121.8(5) ?
C13A C12A H12A . . 119.1 ?
C12A C13A O4A . . 122.9(8) ?
C12A C13A C14A . . 118.8(6) ?
C14A C13A O4A . . 118.0(8) ?
C13A C14A H14A . . 120.1 ?
C13A C14A C15A . . 119.8(5) ?
C15A C14A H14A . . 120.1 ?
C10A C15A C14A . . 121.6(4) ?
C10A C15A H15A . . 119.2 ?
C14A C15A H15A . . 119.2 ?
C13B O4B H4B . . 109.5 ?
O3 C9B C8 . . 115.2(3) ?
O3 C9B H9B . . 105.5 ?
O3 C9B C10B . . 109.5(3) ?
C8 C9B H9B . . 105.5 ?
C8 C9B C10B . . 114.6(3) ?
C10B C9B H9B . . 105.5 ?
C11B C10B C9B . . 119.1(5) ?
C15B C10B C9B . . 122.3(5) ?
C15B C10B C11B . . 118.6(5) ?
C10B C11B H11B . . 119.4 ?
C12B C11B C10B . . 121.1(6) ?
C12B C11B H11B . . 119.4 ?
C11B C12B H12B . . 119.9 ?
C13B C12B C11B . . 120.1(7) ?
C13B C12B H12B . . 119.9 ?
C12B C13B O4B . . 113.9(10) ?
C12B C13B C14B . . 119.6(7) ?
C14B C13B O4B . . 125.5(11) ?
C13B C14B H14B . . 119.9 ?
C13B C14B C15B . . 120.2(7) ?
C15B C14B H14B . . 119.9 ?
C10B C15B C14B . . 120.2(6) ?
C10B C15B H15B . . 119.9 ?
C14B C15B H15B . . 119.9 ?
C23A O5A H5A . . 109.5 ?
H22A C22A H22B . . 109.5 ?
H22A C22A H22C . . 109.5 ?
H22B C22A H22C . . 109.5 ?
C23A C22A H22A . . 109.5 ?
C23A C22A H22B . . 109.5 ?
C23A C22A H22C . . 109.5 ?
O5A C23A H23A . . 104.5 ?
O5A C23A H23B . . 104.5 ?
C22A C23A O5A . . 130.9(14) ?
C22A C23A H23A . . 104.5 ?
C22A C23A H23B . . 104.5 ?
H23A C23A H23B . . 105.7 ?
C23B O5B H5B . . 109.5 ?
H22D C22B H22E . . 109.5 ?
H22D C22B H22F . . 109.5 ?
H22E C22B H22F . . 109.5 ?
C23B C22B H22D . . 109.5 ?
C23B C22B H22E . . 109.5 ?
C23B C22B H22F . . 109.5 ?
O5B C23B H23C . . 108.1 ?
O5B C23B H23D . . 108.1 ?
C22B C23B O5B . . 116.8(12) ?
C22B C23B H23C . . 108.1 ?
C22B C23B H23D . . 108.1 ?
H23C C23B H23D . . 107.3 ?
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 H1 . 0.8200 ?
O1 C1 . 1.3715(18) ?
O2 H2 . 0.8200 ?
O2 C3 . 1.3595(18) ?
O3 C5 . 1.3680(17) ?
O3 C9A . 1.395(3) ?
O3 C9B . 1.380(4) ?
N1 N2 . 1.3604(18) ?
N1 C7 . 1.2953(19) ?
N2 H2A . 0.8600 ?
N2 C16 . 1.3896(18) ?
C1 C2 . 1.386(2) ?
C1 C6 . 1.381(2) ?
C2 H2B . 0.9300 ?
C2 C3 . 1.378(2) ?
C3 C4 . 1.407(2) ?
C4 C5 . 1.402(2) ?
C4 C7 . 1.459(2) ?
C5 C6 . 1.382(2) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.495(2) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C8 H8BC . 0.9700 ?
C8 H8BD . 0.9700 ?
C8 C9A . 1.484(3) ?
C8 C9B . 1.496(4) ?
C16 C17 . 1.389(2) ?
C16 C21 . 1.389(2) ?
C17 H17 . 0.9300 ?
C17 C18 . 1.384(2) ?
C18 H18 . 0.9300 ?
C18 C19 . 1.375(3) ?
C19 H19 . 0.9300 ?
C19 C20 . 1.368(3) ?
C20 H20 . 0.9300 ?
C20 C21 . 1.390(2) ?
C21 H21 . 0.9300 ?
O4A H4A . 0.8200 ?
O4A C13A . 1.376(6) ?
C9A H9A . 0.9800 ?
C9A C10A . 1.505(4) ?
C10A C11A . 1.388(5) ?
C10A C15A . 1.373(5) ?
C11A H11A . 0.9300 ?
C11A C12A . 1.377(5) ?
C12A H12A . 0.9300 ?
C12A C13A . 1.368(5) ?
C13A C14A . 1.375(6) ?
C14A H14A . 0.9300 ?
C14A C15A . 1.380(5) ?
C15A H15A . 0.9300 ?
O4B H4B . 0.8200 ?
O4B C13B . 1.374(7) ?
C9B H9B . 0.9800 ?
C9B C10B . 1.509(5) ?
C10B C11B . 1.380(6) ?
C10B C15B . 1.371(6) ?
C11B H11B . 0.9300 ?
C11B C12B . 1.365(6) ?
C12B H12B . 0.9300 ?
C12B C13B . 1.363(7) ?
C13B C14B . 1.372(7) ?
C14B H14B . 0.9300 ?
C14B C15B . 1.383(6) ?
C15B H15B . 0.9300 ?
O5A H5A . 0.8200 ?
O5A C23A . 1.425(7) ?
C22A H22A . 0.9600 ?
C22A H22B . 0.9600 ?
C22A H22C . 0.9600 ?
C22A C23A . 1.198(13) ?
C23A H23A . 0.9700 ?
C23A H23B . 0.9700 ?
O5B H5B . 0.8200 ?
O5B C23B . 1.462(7) ?
C22B H22D . 0.9600 ?
C22B H22E . 0.9600 ?
C22B H22F . 0.9600 ?
C22B C23B . 1.237(14) ?
C23B H23C . 0.9700 ?
C23B H23D . 0.9700 ?
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
O5A H5A C17 . 0.82 2.56 3.363(15) 166.3 yes
O5A H5A C18 . 0.82 2.47 3.263(16) 161.5 yes
O5B H5B C19 2_666 0.82 2.59 3.405(11) 172.7 yes
O1 H1 O5A 2_666 0.82 1.79 2.590(12) 166.0 yes
O1 H1 O5B . 0.82 1.90 2.709(8) 170.1 yes
C8 H8BC O4B 2_677 0.97 2.49 3.440(17) 167.5 yes
O4A H4A O1 1_566 0.82 1.89 2.677(13) 160.3 yes
C9B H9B O2 2_666 0.98 2.39 3.347(5) 165.2 yes
O2 H2 N1 1_555 0.82 1.873 2.5975(18) 146.7 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 C1 C2 C3 . . . . 178.29(15) ?
O1 C1 C6 C5 . . . . -178.82(15) ?
O2 C3 C4 C5 . . . . -179.31(15) ?
O2 C3 C4 C7 . . . . 0.1(3) ?
O3 C5 C6 C1 . . . . -179.85(14) ?
O3 C9A C10A C11A . . . . -65.7(5) ?
O3 C9A C10A C15A . . . . 113.9(4) ?
O3 C9B C10B C11B . . . . -120.8(6) ?
O3 C9B C10B C15B . . . . 61.0(6) ?
N1 N2 C16 C17 . . . . -175.73(15) ?
N1 N2 C16 C21 . . . . 4.2(3) ?
N1 C7 C8 C9A . . . . -164.3(2) ?
N1 C7 C8 C9B . . . . 153.3(2) ?
N2 N1 C7 C4 . . . . -178.82(13) ?
N2 N1 C7 C8 . . . . 1.6(2) ?
N2 C16 C17 C18 . . . . 179.73(17) ?
N2 C16 C21 C20 . . . . -179.91(17) ?
C1 C2 C3 O2 . . . . -179.82(15) ?
C1 C2 C3 C4 . . . . 0.7(3) ?
C2 C1 C6 C5 . . . . 0.4(3) ?
C2 C3 C4 C5 . . . . 0.2(2) ?
C2 C3 C4 C7 . . . . 179.60(15) ?
C3 C4 C5 O3 . . . . 179.56(14) ?
C3 C4 C5 C6 . . . . -0.8(2) ?
C3 C4 C7 N1 . . . . 5.3(2) ?
C3 C4 C7 C8 . . . . -175.16(15) ?
C4 C5 C6 C1 . . . . 0.5(3) ?
C4 C7 C8 C9A . . . . 16.1(3) ?
C4 C7 C8 C9B . . . . -26.2(3) ?
C5 O3 C9A C8 . . . . 48.0(3) ?
C5 O3 C9A C10A . . . . 177.4(2) ?
C5 O3 C9B C8 . . . . -44.8(4) ?
C5 O3 C9B C10B . . . . -175.9(3) ?
C5 C4 C7 N1 . . . . -175.36(14) ?
C5 C4 C7 C8 . . . . 4.2(2) ?
C6 C1 C2 C3 . . . . -1.0(3) ?
C7 N1 N2 C16 . . . . -172.39(14) ?
C7 C4 C5 O3 . . . . 0.1(2) ?
C7 C4 C5 C6 . . . . 179.81(14) ?
C7 C8 C9A O3 . . . . -42.0(3) ?
C7 C8 C9A C10A . . . . -168.4(3) ?
C7 C8 C9B O3 . . . . 46.7(4) ?
C7 C8 C9B C10B . . . . 175.3(3) ?
C8 C9A C10A C11A . . . . 64.1(5) ?
C8 C9A C10A C15A . . . . -116.3(4) ?
C8 C9B C10B C11B . . . . 107.9(6) ?
C8 C9B C10B C15B . . . . -70.3(6) ?
C16 C17 C18 C19 . . . . 0.4(3) ?
C17 C16 C21 C20 . . . . 0.0(3) ?
C17 C18 C19 C20 . . . . -0.5(3) ?
C18 C19 C20 C21 . . . . 0.3(3) ?
C19 C20 C21 C16 . . . . 0.0(3) ?
C21 C16 C17 C18 . . . . -0.2(3) ?
O4A C13A C14A C15A . . . . -177.1(16) ?
C9A O3 C5 C4 . . . . -26.8(3) ?
C9A O3 C5 C6 . . . . 153.5(2) ?
C9A C10A C11A C12A . . . . -179.9(7) ?
C9A C10A C15A C14A . . . . -179.2(6) ?
C10A C11A C12A C13A . . . . -2.8(18) ?
C11A C10A C15A C14A . . . . 0.4(9) ?
C11A C12A C13A O4A . . . . 177.8(18) ?
C11A C12A C13A C14A . . . . 4(3) ?
C12A C13A C14A C15A . . . . -3(3) ?
C13A C14A C15A C10A . . . . 0.8(18) ?
C15A C10A C11A C12A . . . . 0.6(9) ?
O4B C13B C14B C15B . . . . 170(2) ?
C9B O3 C5 C4 . . . . 20.7(3) ?
C9B O3 C5 C6 . . . . -159.0(3) ?
C9B C10B C11B C12B . . . . 178.9(9) ?
C9B C10B C15B C14B . . . . -179.8(9) ?
C10B C11B C12B C13B . . . . 3(2) ?
C11B C10B C15B C14B . . . . 1.9(12) ?
C11B C12B C13B O4B . . . . -172(2) ?
C11B C12B C13B C14B . . . . -3(4) ?
C12B C13B C14B C15B . . . . 2(4) ?
C13B C14B C15B C10B . . . . -2(2) ?
C15B C10B C11B C12B . . . . -2.8(12) ?
