#------------------------------------------------------------------------------
#$Date: 2022-01-01 06:12:12 +0200 (Sat, 01 Jan 2022) $
#$Revision: 271662 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/88/2108894.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_2108894
loop_
_publ_author_name
'Iqbal, Alia'
'Mehmood, Arshad'
'Noureen, Sajida'
'Lecomte, Claude'
'Ahmed, Maqsood'
_publ_section_title
;
 Crystal engineering of co-crystal of nicotinic acid and pyrogallol: an
 experimental and theoretical electron density analysis
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              1035
_journal_page_last               1047
_journal_paper_doi               10.1107/S2052520621009124
_journal_volume                  77
_journal_year                    2021
_chemical_formula_moiety         'C6 H5 N O2, C6 H6 O3'
_chemical_formula_sum            'C12 H11 N O5'
_chemical_formula_weight         249.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'MoPro v20.06             '
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.6648(4)
_cell_length_b                   11.9321(3)
_cell_length_c                   12.9678(4)
_cell_measurement_reflns_used    2780
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      52.2
_cell_measurement_theta_min      2.27
_cell_volume                     2114.40(10)
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II'
_diffrn_measurement_method       'omega and phi scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.04235
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            101259
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         52.201
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.7503
_exptl_absorpt_correction_T_min  0.6752
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0673 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.8999.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.286
_exptl_crystal_size_min          0.243
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.34
_refine_ls_abs_structure_details 'Rogers (1981),  8469 Friedel pairs'
_refine_ls_abs_structure_Rogers  1.
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1075
_refine_ls_number_reflns         19169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.000
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'calc w =1/[1.223*σ²(Fo²)+0.0001*Yo²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0383
_refine_ls_wR_factor_ref         0.046
_reflns_number_gt                19169
_reflns_number_total             19169
_reflns_threshold_expression     '>2.0 sigma(I)'
_cod_data_source_file            px5041sup1.cif
_cod_data_source_block           multipolar_MoPro
_cod_database_code               2108894
_publcif_datablock.id            {92b6ae7c-a2c6-4311-80ce-f7f591ff9229}
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.958
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, 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_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.68090(2) 0.64338(3) 0.547620(6) 0.015210(14) Uani 1 d . . . .
N N1 0.68875(2) 0.35065(3) 0.37576(4) 0.011509(13) Uani 1 d . . . .
H H1 0.68420 0.27141 0.41620 0.02558 Uani 1 d R U . .
C C1 0.68309(3) 0.44392(3) 0.43328(4) 0.010812(14) Uani 1 d . . . .
H H1A 0.66960 0.42702 0.51436 0.02649 Uani 1 d R U . .
O O2 0.68742(2) 0.74541(3) 0.40319(4) 0.017211(15) Uani 1 d . . . .
N N2 0.67965(2) -0.14701(3) 0.62887(3) 0.011375(13) Uani 1 d . . . .
H H2 0.67924 -0.22524 0.58805 0.02593 Uani 1 d R U . .
C C2 0.68698(2) 0.54858(3) 0.38670(4) 0.010287(14) Uani 1 d . . . .
O O3 0.68263(2) 0.14660(3) 0.46002(3) 0.015081(14) Uani 1 d . . . .
C C3 0.69544(3) 0.55390(3) 0.27960(4) 0.012285(15) Uani 1 d . . . .
H H3 0.70080 0.63357 0.23922 0.02621 Uani 1 d R U . .
O O4 0.67786(2) 0.24881(3) 0.60438(4) 0.015723(13) Uani 1 d . . . .
C C4 0.70135(3) 0.45585(3) 0.22178(4) 0.013279(16) Uani 1 d . . . .
H H4 0.71476 0.45861 0.13934 0.02551 Uani 1 d R U . .
C C5 0.69796(3) 0.35401(3) 0.27262(4) 0.012910(16) Uani 1 d . . . .
H H5 0.70442 0.27493 0.23204 0.02345 Uani 1 d R U . .
O O5 0.56144(2) 0.40676(2) 0.68628(3) 0.014828(13) Uani 1 d . . . .
H H5A 0.59914 0.33578 0.68516 0.02559 Uani 1 d R U . .
O O6 0.58028(2) 0.28220(2) 0.86722(4) 0.016431(13) Uani 1 d . . . .
H H6 0.57488 0.24894 0.93655 0.02326 Uani 1 d R U . .
C C6 0.68411(3) 0.65407(3) 0.45043(4) 0.011740(15) Uani 1 d . . . .
C C7 0.68004(3) -0.05256(3) 0.57242(4) 0.011191(15) Uani 1 d . . . .
H H7 0.68071 -0.06829 0.49002 0.02381 Uani 1 d R U . .
O O7 0.54119(2) 0.63227(2) 0.69511(3) 0.013985(12) Uani 1 d . . . .
H H7A 0.58036 0.59732 0.63949 0.02620 Uani 1 d R U . .
O O8 0.57053(2) 1.13634(2) 0.28401(3) 0.014451(12) Uani 1 d . . . .
H H8 0.60116 1.10197 0.34559 0.02487 Uani 1 d R U . .
C C8 0.67818(2) 0.05129(3) 0.62078(4) 0.010193(14) Uani 1 d . . . .
C C9 0.67578(3) 0.05494(3) 0.72828(4) 0.012078(15) Uani 1 d . . . .
H H9 0.67177 0.13523 0.76801 0.02486 Uani 1 d R U . .
O O9 0.54931(2) 1.19663(2) 0.07989(4) 0.015353(13) Uani 1 d . . . .
H H9A 0.52751 1.24376 0.13812 0.02641 Uani 1 d R U . .
C C10 0.67774(3) -0.04438(3) 0.78495(4) 0.012692(15) Uani 1 d . . . .
H H10 0.67737 -0.04356 0.86869 0.02400 Uani 1 d R U . .
O O10 0.58562(2) 0.91928(2) 0.33847(3) 0.014056(13) Uani 1 d . . . .
H H10A 0.61384 0.84387 0.35324 0.02639 Uani 1 d R U . .
C C11 0.67919(3) -0.14549(3) 0.73257(4) 0.012351(15) Uani 1 d . . . .
H H11 0.68115 -0.22669 0.77022 0.02658 Uani 1 d R U . .
C C12 0.67898(3) 0.15756(3) 0.55730(4) 0.011442(15) Uani 1 d . . . .
C C13 0.56219(2) 0.45555(3) 0.78113(4) 0.010470(13) Uani 1 d . . . .
C C14 0.57028(2) 0.39612(3) 0.87400(4) 0.011408(14) Uani 1 d . . . .
C C15 0.56856(3) 0.45315(3) 0.96799(4) 0.013364(16) Uani 1 d . . . .
H H15 0.57734 0.40278 1.03727 0.02636 Uani 1 d R U . .
C C16 0.55731(3) 0.56930(3) 0.97008(4) 0.014164(16) Uani 1 d . . . .
H H16 0.55366 0.61271 1.04369 0.02659 Uani 1 d R U . .
C C17 0.54835(3) 0.62915(3) 0.87837(4) 0.012971(15) Uani 1 d . . . .
H H17 0.53055 0.71786 0.87439 0.02712 Uani 1 d R U . .
C C18 0.55113(2) 0.57221(3) 0.78479(4) 0.010619(13) Uani 1 d . . . .
C C19 0.56858(2) 1.05468(3) 0.21025(4) 0.010177(14) Uani 1 d . . . .
C C20 0.55765(2) 1.08586(3) 0.10726(4) 0.011211(14) Uani 1 d . . . .
C C21 0.55605(3) 1.00476(3) 0.02999(4) 0.014420(17) Uani 1 d . . . .
H H21 0.54060 1.03286 -0.04810 0.02647 Uani 1 d R U . .
C C22 0.56525(3) 0.89216(4) 0.05637(4) 0.016084(17) Uani 1 d . . . .
H H22 0.56100 0.82864 -0.00360 0.02600 Uani 1 d R U . .
C C23 0.57464(3) 0.85922(3) 0.15933(4) 0.013821(16) Uani 1 d . . . .
H H23 0.58265 0.77247 0.18401 0.02656 Uani 1 d R U . .
C C24 0.57651(3) 0.94088(3) 0.23599(4) 0.010626(14) Uani 1 d . . . .
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 122.26(3) . . . ?
C1 N1 H1 116.84 . . . ?
C5 N1 H1 120.89 . . . ?
N1 C1 C2 120.13(3) . . . ?
N1 C1 H1A 113.20 . . . ?
C2 C1 H1A 126.48 . . . ?
C7 N2 C11 122.23(3) . . . ?
C7 N2 H2 117.43 . . . ?
C11 N2 H2 120.33 . . . ?
C6 C2 C1 120.80(3) . . . ?
C6 C2 C3 120.68(3) . . . ?
C1 C2 C3 118.51(3) . . . ?
C2 C3 C4 120.18(3) . . . ?
C2 C3 H3 121.64 . . . ?
C4 C3 H3 118.12 . . . ?
C5 C4 C3 118.67(3) . . . ?
C5 C4 H4 120.12 . . . ?
C3 C4 H4 120.99 . . . ?
N1 C5 C4 120.24(3) . . . ?
N1 C5 H5 117.69 . . . ?
C4 C5 H5 122.05 . . . ?
C13 O5 H5A 112.01 . . . ?
C14 O6 H6 109.50 . . . ?
O2 C6 O1 125.16(3) . . . ?
O2 C6 C2 117.28(3) . . . ?
O1 C6 C2 117.54(3) . . . ?
N2 C7 C8 120.14(3) . . . ?
N2 C7 H7 113.04 . . . ?
C8 C7 H7 126.81 . . . ?
C18 O7 H7A 110.11 . . . ?
C19 O8 H8 106.11 . . . ?
C12 C8 C7 120.15(3) . . . ?
C12 C8 C9 121.20(3) . . . ?
C7 C8 C9 118.64(3) . . . ?
C8 C9 C10 119.97(3) . . . ?
C8 C9 H9 120.08 . . . ?
C10 C9 H9 119.94 . . . ?
C20 O9 H9A 112.05 . . . ?
C11 C10 C9 118.82(3) . . . ?
C11 C10 H10 119.90 . . . ?
C9 C10 H10 121.27 . . . ?
C24 O10 H10A 113.21 . . . ?
N2 C11 C10 120.16(3) . . . ?
N2 C11 H11 115.95 . . . ?
C10 C11 H11 123.88 . . . ?
O4 C12 O3 125.19(3) . . . ?
O4 C12 C8 117.73(3) . . . ?
O3 C12 C8 117.07(3) . . . ?
O5 C13 C18 117.06(3) . . . ?
O5 C13 C14 124.10(3) . . . ?
C18 C13 C14 118.81(3) . . . ?
O6 C14 C13 117.06(3) . . . ?
O6 C14 C15 122.80(3) . . . ?
C13 C14 C15 120.14(3) . . . ?
C14 C15 C16 120.21(3) . . . ?
C14 C15 H15 116.74 . . . ?
C16 C15 H15 123.05 . . . ?
C17 C16 C15 120.18(3) . . . ?
C17 C16 H16 120.09 . . . ?
C15 C16 H16 119.71 . . . ?
C18 C17 C16 119.47(3) . . . ?
C18 C17 H17 116.11 . . . ?
C16 C17 H17 124.02 . . . ?
O7 C18 C13 120.04(3) . . . ?
O7 C18 C17 118.77(3) . . . ?
C13 C18 C17 121.18(3) . . . ?
O8 C19 C20 118.85(3) . . . ?
O8 C19 C24 121.51(3) . . . ?
C20 C19 C24 119.64(3) . . . ?
O9 C20 C19 120.87(3) . . . ?
O9 C20 C21 118.78(3) . . . ?
C19 C20 C21 120.35(3) . . . ?
C20 C21 C22 119.48(3) . . . ?
C20 C21 H21 117.30 . . . ?
C22 C21 H21 122.96 . . . ?
C21 C22 C23 120.96(3) . . . ?
C21 C22 H22 119.47 . . . ?
C23 C22 H22 119.48 . . . ?
C24 C23 C22 119.14(3) . . . ?
C24 C23 H23 116.97 . . . ?
C22 C23 H23 123.87 . . . ?
O10 C24 C19 115.04(3) . . . ?
O10 C24 C23 124.55(3) . . . ?
C19 C24 C23 120.41(3) . . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.2675(5) . ?
N1 C1 1.3420(5) . ?
N1 C5 1.3440(5) . ?
N1 H1 1.08292 . ?
C1 C2 1.3883(5) . ?
C1 H1A 1.08629 . ?
O2 C6 1.2511(5) . ?
N2 C7 1.3439(5) . ?
N2 C11 1.3449(5) . ?
N2 H2 1.07311 . ?
C2 C6 1.5063(5) . ?
C2 C3 1.3951(5) . ?
O3 C12 1.2693(5) . ?
C3 C4 1.3920(5) . ?
C3 H3 1.08774 . ?
O4 C12 1.2484(5) . ?
C4 C5 1.3832(6) . ?
C4 H4 1.08523 . ?
C5 H5 1.08397 . ?
O5 C13 1.3609(5) . ?
O5 H5A 0.99142 . ?
O6 C14 1.3690(5) . ?
O6 H6 0.98548 . ?
C7 C8 1.3890(5) . ?
C7 H7 1.08501 . ?
O7 C18 1.3728(5) . ?
O7 H7A 0.99031 . ?
O8 C19 1.3657(4) . ?
O8 H8 0.99054 . ?
C8 C12 1.5117(5) . ?
C8 C9 1.3952(5) . ?
C9 C10 1.3947(5) . ?
C9 H9 1.08916 . ?
O9 C20 1.3733(5) . ?
O9 H9A 0.98743 . ?
C10 C11 1.3846(5) . ?
C10 H10 1.08597 . ?
O10 C24 1.3595(5) . ?
O10 H10A 0.99748 . ?
C11 H11 1.08532 . ?
C13 C18 1.4009(5) . ?
C13 C14 1.4020(5) . ?
C14 C15 1.3961(5) . ?
C15 C16 1.3947(6) . ?
C15 H15 1.08750 . ?
C16 C17 1.3926(6) . ?
C16 H16 1.08721 . ?
C17 C18 1.3913(5) . ?
C17 H17 1.08734 . ?
C19 C20 1.3945(5) . ?
C19 C24 1.4025(5) . ?
C20 C21 1.3931(5) . ?
C21 C22 1.3921(6) . ?
C21 H21 1.08736 . ?
C22 C23 1.3976(6) . ?
C22 H22 1.08760 . ?
C23 C24 1.3921(5) . ?
C23 H23 1.08901 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 1.073 1.6531 2.7140(4) 168.878(11) 1_545
N2 H2 O2 1.073 2.4253 3.1975(5) 127.81(3) 1_545
N2 H2 C6 1.073 2.2941 3.3153(5) 158.376(14) 1_545
C5 H5 O8 1.084 2.5566 3.1304(5) 112 1_545
C7 H7 O2 1.085 2.4935 3.2615(5) 126 1_545
C7 H7 O10 1.085 2.3605 3.3138(5) 145 1_545
O6 H6 O9 0.985 1.9917 2.9711(5) 172.191(5) 1_546
C15 H15 O9 1.087 2.5500 3.3975(5) 134 1_546
N1 H1 O3 1.083 1.5942 2.6700(4) 171.495(11) 1
N1 H1 O4 1.083 2.4567 3.2075(5) 125.37(3) 1
N1 H1 C12 1.083 2.2802 3.2968(5) 155.586(17) 1
C1 H1A O4 1.086 2.4284 3.2168(5) 128 1
O5 H5A O4 0.991 1.8252 2.6853(4) 143.16(2) 1
O7 H7A O1 0.990 1.8997 2.7056(4) 136.54(2) 1
O8 H8 O10 0.991 2.1921 2.6925(4) 109.689(19) 1
C9 H9 O6 1.089 2.5087 3.5076(5) 151 1
O9 H9A O8 0.987 2.3595 2.7582(4) 103.22(2) 1
O10 H10A O2 0.997 1.6765 2.6350(4) 159.738(16) 1
O8 H8 O3 0.991 1.9300 2.7515(4) 138 1_565
C11 H11 O2 1.085 2.5119 3.1485(5) 116 4_645
C5 H5 O4 1.084 2.3292 3.0356(5) 121 4_654
C16 H16 O5 1.087 2.4386 3.2519(5) 130 2_665
O9 H9A O7 0.987 1.9016 2.8160(4) 152.756(17) 2_674
C21 H21 O10 1.087 2.3376 3.2767(5) 143 2_674
C17 H17 O8 1.087 2.5115 3.4592(5) 145 2_675
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 C6 C2 C1 . . . . 1.99(5) ?
O1 C6 C2 C3 . . . . -176.82(5) ?
N1 C1 C2 C6 . . . . -177.94(5) ?
N1 C1 C2 C3 . . . . 0.88(5) ?
N1 C5 C4 C3 . . . . 0.25(5) ?
N1 C5 C4 H4 . . . . 174.97 ?
H1 N1 C1 C2 . . . . -179.09 ?
H1 N1 C1 H1A . . . . -3.84 ?
H1 N1 C5 C4 . . . . 178.46 ?
H1 N1 C5 H5 . . . . -3.10 ?
C1 N1 C5 C4 . . . . -0.38(5) ?
C1 N1 C5 H5 . . . . 178.06 ?
C1 C2 C6 O2 . . . . -179.65(5) ?
C1 C2 C3 C4 . . . . -1.00(5) ?
C1 C2 C3 H3 . . . . -178.31 ?
H1A C1 N1 C5 . . . . 175.05 ?
H1A C1 C2 C6 . . . . 7.49 ?
H1A C1 C2 C3 . . . . -173.68 ?
O2 C6 C2 C3 . . . . 1.55(5) ?
N2 C7 C8 C12 . . . . 179.79(5) ?
N2 C7 C8 C9 . . . . -0.09(5) ?
N2 C11 C10 C9 . . . . 0.65(5) ?
N2 C11 C10 H10 . . . . 180.00 ?
H2 N2 C7 C8 . . . . 178.44 ?
H2 N2 C7 H7 . . . . -0.64 ?
H2 N2 C11 C10 . . . . -178.71 ?
H2 N2 C11 H11 . . . . 2.21 ?
C2 C1 N1 C5 . . . . -0.20(5) ?
C2 C3 C4 C5 . . . . 0.45(5) ?
C2 C3 C4 H4 . . . . -174.22 ?
O3 C12 C8 C7 . . . . -0.87(5) ?
O3 C12 C8 C9 . . . . 179.00(5) ?
C3 C4 C5 H5 . . . . -178.12 ?
H3 C3 C2 C6 . . . . 0.52 ?
H3 C3 C4 C5 . . . . 177.84 ?
H3 C3 C4 H4 . . . . 3.18 ?
O4 C12 C8 C7 . . . . -179.55(5) ?
O4 C12 C8 C9 . . . . 0.32(5) ?
C4 C3 C2 C6 . . . . 177.83(5) ?
H4 C4 C5 H5 . . . . -3.40 ?
O5 C13 C18 O7 . . . . -0.67(4) ?
O5 C13 C18 C17 . . . . 178.26(5) ?
O5 C13 C14 O6 . . . . 1.57(4) ?
O5 C13 C14 C15 . . . . -178.80(5) ?
H5A O5 C13 C18 . . . . 152.88 ?
H5A O5 C13 C14 . . . . -29.12 ?
O6 C14 C13 C18 . . . . 179.54(5) ?
O6 C14 C15 C16 . . . . -179.43(5) ?
O6 C14 C15 H15 . . . . 1.39 ?
H6 O6 C14 C13 . . . . -171.20 ?
H6 O6 C14 C15 . . . . 9.18 ?
C7 N2 C11 C10 . . . . 0.88(5) ?
C7 N2 C11 H11 . . . . -178.19 ?
C7 C8 C9 C10 . . . . 1.59(5) ?
C7 C8 C9 H9 . . . . -177.90 ?
H7 C7 N2 C11 . . . . 179.75 ?
H7 C7 C8 C12 . . . . -1.27 ?
H7 C7 C8 C9 . . . . 178.85 ?
O7 C18 C13 C14 . . . . -178.78(4) ?
O7 C18 C17 C16 . . . . 179.34(4) ?
O7 C18 C17 H17 . . . . 6.29 ?
H7A O7 C18 C13 . . . . -34.06 ?
H7A O7 C18 C17 . . . . 146.99 ?
O8 C19 C20 O9 . . . . 0.24(5) ?
O8 C19 C20 C21 . . . . 179.55(5) ?
O8 C19 C24 O10 . . . . 0.30(4) ?
O8 C19 C24 C23 . . . . -179.79(5) ?
H8 O8 C19 C20 . . . . -160.67 ?
H8 O8 C19 C24 . . . . 19.86 ?
C8 C7 N2 C11 . . . . -1.17(5) ?
C8 C9 C10 C11 . . . . -1.87(5) ?
C8 C9 C10 H10 . . . . 178.79 ?
C9 C10 C11 H11 . . . . 179.65 ?
H9 C9 C8 C12 . . . . 2.22 ?
H9 C9 C10 C11 . . . . 177.63 ?
H9 C9 C10 H10 . . . . -1.71 ?
O9 C20 C19 C24 . . . . 179.73(5) ?
O9 C20 C21 C22 . . . . 179.46(5) ?
O9 C20 C21 H21 . . . . -6.22 ?
H9A O9 C20 C19 . . . . -21.35 ?
H9A O9 C20 C21 . . . . 159.33 ?
C10 C9 C8 C12 . . . . -178.28(5) ?
H10 C10 C11 H11 . . . . -1.00 ?
O10 C24 C19 C20 . . . . -179.17(4) ?
O10 C24 C23 C22 . . . . -179.79(5) ?
O10 C24 C23 H23 . . . . -1.35 ?
H10A O10 C24 C19 . . . . -159.93 ?
H10A O10 C24 C23 . . . . 20.17 ?
C13 C18 C17 C16 . . . . 0.40(5) ?
C13 C18 C17 H17 . . . . -172.65 ?
C13 C14 C15 C16 . . . . 0.96(5) ?
C13 C14 C15 H15 . . . . -178.22 ?
C14 C13 C18 C17 . . . . 0.15(5) ?
C14 C15 C16 C17 . . . . -0.41(5) ?
C14 C15 C16 H16 . . . . 178.01 ?
C15 C14 C13 C18 . . . . -0.83(5) ?
C15 C16 C17 C18 . . . . -0.27(5) ?
C15 C16 C17 H17 . . . . 172.20 ?
H15 C15 C16 C17 . . . . 178.72 ?
H15 C15 C16 H16 . . . . -2.86 ?
H16 C16 C17 C18 . . . . -178.68 ?
H16 C16 C17 H17 . . . . -6.21 ?
C19 C20 C21 C22 . . . . 0.14(5) ?
C19 C20 C21 H21 . . . . 174.46 ?
C19 C24 C23 C22 . . . . 0.31(5) ?
C19 C24 C23 H23 . . . . 178.75 ?
C20 C19 C24 C23 . . . . 0.74(5) ?
C20 C21 C22 C23 . . . . 0.94(5) ?
C20 C21 C22 H22 . . . . 177.49 ?
C21 C20 C19 C24 . . . . -0.96(5) ?
C21 C22 C23 C24 . . . . -1.16(6) ?
C21 C22 C23 H23 . . . . -179.48 ?
H21 C21 C22 C23 . . . . -173.05 ?
H21 C21 C22 H22 . . . . 3.51 ?
H22 C22 C23 C24 . . . . -177.71 ?
H22 C22 C23 H23 . . . . 3.97 ?
