#------------------------------------------------------------------------------
#$Date: 2022-10-05 04:56:33 +0300 (Wed, 05 Oct 2022) $
#$Revision: 278353 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/41/2244193.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_2244193
loop_
_publ_author_name
'Steiger, Scott A.'
'Li, Chun'
'Oliver, Allen G.'
'Natale, Nicholas R.'
_publ_section_title
;
 Synthesis, crystal structures, and Hirshfeld analysis of three
 hexahydroquinoline derivatives
;
_journal_coeditor_code           JY2021
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022009495
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C22 H27 N O4'
_chemical_formula_moiety         'C22 H27 N O4'
_chemical_formula_sum            'C22 H27 N O4'
_chemical_formula_weight         369.44
_chemical_name_systematic
'Ethyl 4-(4-methoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.0834(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.3492(15)
_cell_length_b                   14.0314(14)
_cell_length_c                   18.3862(18)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    120.00
_cell_measurement_theta_max      26.42
_cell_measurement_theta_min      2.26
_cell_volume                     3959.8(7)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018/1 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS  (Sheldrick, 2008)
;
_diffrn_ambient_temperature      120.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            66519
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.376
_diffrn_reflns_theta_min         1.327
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.135
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.298
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     536
_refine_ls_number_reflns         8085
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0433P)²+1.0284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0934
_reflns_number_gt                7121
_reflns_number_total             8085
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jy2021sup1.cif
_cod_data_source_block           II
_cod_database_code               2244193
_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   0.971
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 O1A 0.45938(8) 1.14027(8) 0.37758(7) 0.0261(3) Uani d 1 . .
O O2A 0.83266(9) 0.94867(10) 0.38491(8) 0.0353(3) Uani d 1 . .
O O3A 0.76656(8) 1.07646(9) 0.33709(7) 0.0239(3) Uani d 1 . .
O O4A 0.58302(9) 1.01706(9) 0.04318(7) 0.0279(3) Uani d 1 . .
N N1A 0.57551(10) 0.83505(11) 0.40985(8) 0.0195(3) Uani d 1 . .
H H1A 0.5659(13) 0.7789(15) 0.4186(11) 0.023(5) Uiso d 1 . .
C C2A 0.66070(11) 0.86446(12) 0.39877(9) 0.0196(4) Uani d 1 . .
C C3A 0.67643(11) 0.95409(12) 0.37482(9) 0.0186(4) Uani d 1 . .
C C4A 0.60238(10) 1.01965(12) 0.35175(9) 0.0175(3) Uani d 1 . .
H H4A 0.616041 1.085397 0.369398 0.021 Uiso calc 1 . .
C C5A 0.44879(11) 1.05602(12) 0.39480(9) 0.0182(4) Uani d 1 . .
C C6A 0.36366(11) 1.02348(12) 0.42708(10) 0.0200(4) Uani d 1 . .
H H6AA 0.315982 1.062202 0.406008 0.024 Uiso calc 1 . .
H H6AB 0.364850 1.035734 0.480100 0.024 Uiso calc 1 . .
C C7A 0.34314(11) 0.91751(12) 0.41443(9) 0.0193(4) Uani d 1 . .
C C8A 0.42224(11) 0.85979(12) 0.43937(9) 0.0186(3) Uani d 1 . .
H H8AA 0.424860 0.860609 0.493173 0.022 Uiso calc 1 . .
H H8AB 0.414748 0.792748 0.423785 0.022 Uiso calc 1 . .
C C9A 0.50663(11) 0.89679(12) 0.40982(9) 0.0170(3) Uani d 1 . .
C C10A 0.51830(11) 0.98787(12) 0.38714(9) 0.0167(3) Uani d 1 . .
C C11A 0.32322(12) 0.90078(13) 0.33413(10) 0.0248(4) Uani d 1 . .
H H11D 0.275190 0.942331 0.318973 0.037 Uiso calc 1 . .
H H11E 0.306604 0.834047 0.326715 0.037 Uiso calc 1 . .
H H11F 0.375071 0.915231 0.305108 0.037 Uiso calc 1 . .
C C12A 0.26398(12) 0.88893(13) 0.45999(11) 0.0266(4) Uani d 1 . .
H H12D 0.276470 0.900163 0.511574 0.040 Uiso calc 1 . .
H H12E 0.251289 0.821217 0.452347 0.040 Uiso calc 1 . .
H H12F 0.213502 0.927113 0.445243 0.040 Uiso calc 1 . .
C C13A 0.72712(12) 0.79058(13) 0.41851(11) 0.0263(4) Uani d 1 . .
H H13D 0.752914 0.806281 0.465804 0.039 Uiso calc 1 . .
H H13E 0.772869 0.789171 0.381402 0.039 Uiso calc 1 . .
H H13F 0.699027 0.727966 0.421239 0.039 Uiso calc 1 . .
C C14A 0.76640(11) 0.98918(13) 0.36709(9) 0.0214(4) Uani d 1 . .
C C15A 0.85044(12) 1.11883(14) 0.32108(11) 0.0289(4) Uani d 1 . .
H H15E 0.893385 1.068708 0.308859 0.035 Uiso calc 1 . .
H H15F 0.872177 1.154790 0.363730 0.035 Uiso calc 1 . .
C C16A 0.83761(13) 1.18449(14) 0.25765(12) 0.0352(5) Uani d 1 . .
H H16G 0.811091 1.149255 0.217271 0.053 Uiso calc 1 . .
H H16H 0.894095 1.210040 0.242322 0.053 Uiso calc 1 . .
H H16I 0.799255 1.237092 0.271891 0.053 Uiso calc 1 . .
C C17A 0.59364(10) 1.02320(12) 0.26930(9) 0.0177(4) Uani d 1 . .
C C18A 0.57574(11) 0.93988(12) 0.23039(9) 0.0214(4) Uani d 1 . .
H H18A 0.565952 0.882052 0.255969 0.026 Uiso calc 1 . .
C C19A 0.57207(11) 0.94030(13) 0.15539(10) 0.0218(4) Uani d 1 . .
H H19A 0.560018 0.882987 0.129776 0.026 Uiso calc 1 . .
C C20A 0.58598(11) 1.02449(13) 0.11729(9) 0.0217(4) Uani d 1 . .
C C21A 0.60189(11) 1.10830(13) 0.15485(10) 0.0232(4) Uani d 1 . .
H H21A 0.610207 1.166456 0.129332 0.028 Uiso calc 1 . .
C C22A 0.60553(11) 1.10619(12) 0.23063(10) 0.0216(4) Uani d 1 . .
H H22A 0.616536 1.163699 0.256321 0.026 Uiso calc 1 . .
C C23A 0.58707(15) 1.10334(15) 0.00256(11) 0.0359(5) Uani d 1 . .
H H23D 0.581901 1.088987 -0.049428 0.054 Uiso calc 1 . .
H H23E 0.642866 1.135061 0.011879 0.054 Uiso calc 1 . .
H H23F 0.539242 1.145358 0.017281 0.054 Uiso calc 1 . .
O O1B 0.53248(9) 0.63931(8) 0.41653(7) 0.0275(3) Uani d 1 . .
O O2B 0.16407(8) 0.44710(11) 0.34002(8) 0.0367(3) Uani d 1 . .
O O4B 0.45174(10) 0.69033(9) 0.07234(7) 0.0325(3) Uani d 1 . .
N N1B 0.41867(10) 0.33580(11) 0.37064(9) 0.0232(3) Uani d 1 . .
H H1B 0.4275(14) 0.2749(16) 0.3763(12) 0.037(6) Uiso d 1 . .
C C2B 0.33400(11) 0.36815(12) 0.36142(10) 0.0224(4) Uani d 1 . .
C C3B 0.31849(11) 0.46259(13) 0.35623(10) 0.0226(4) Uani d 1 . .
C C4B 0.39216(11) 0.53471(12) 0.35400(10) 0.0201(4) Uani d 1 . .
H H4B 0.375782 0.589307 0.386149 0.024 Uiso calc 1 . .
C C5B 0.54390(12) 0.55231(12) 0.41031(9) 0.0207(4) Uani d 1 . .
C C6B 0.62933(12) 0.50822(13) 0.43392(10) 0.0236(4) Uani d 1 . .
H H6BA 0.629257 0.502553 0.487587 0.028 Uiso calc 1 . .
H H6BB 0.677155 0.552131 0.420484 0.028 Uiso calc 1 . .
C C7B 0.64891(12) 0.41011(13) 0.40149(10) 0.0223(4) Uani d 1 . .
C C8B 0.56843(11) 0.34797(12) 0.41231(10) 0.0221(4) Uani d 1 . .
H H8BA 0.576211 0.287574 0.385247 0.026 Uiso calc 1 . .
H H8BB 0.562928 0.332075 0.464561 0.026 Uiso calc 1 . .
C C9B 0.48608(11) 0.39520(12) 0.38717(10) 0.0195(4) Uani d 1 . .
C C10B 0.47532(11) 0.49112(12) 0.38389(10) 0.0190(4) Uani d 1 . .
C C11B 0.67057(13) 0.41894(14) 0.32069(10) 0.0290(4) Uani d 1 . .
H H11A 0.681145 0.355422 0.300374 0.044 Uiso calc 1 . .
H H11B 0.722849 0.458254 0.314753 0.044 Uiso calc 1 . .
H H11C 0.621608 0.448806 0.295120 0.044 Uiso calc 1 . .
C C12B 0.72593(12) 0.36470(15) 0.44191(12) 0.0314(5) Uani d 1 . .
H H12A 0.711607 0.358440 0.493620 0.047 Uiso calc 1 . .
H H12B 0.777587 0.405106 0.436484 0.047 Uiso calc 1 . .
H H12C 0.737796 0.301528 0.421460 0.047 Uiso calc 1 . .
C C13B 0.26813(12) 0.28863(14) 0.35968(12) 0.0323(5) Uani d 1 . .
H H13A 0.297954 0.227423 0.365980 0.048 Uiso calc 1 . .
H H13B 0.237582 0.289167 0.312845 0.048 Uiso calc 1 . .
H H13C 0.226000 0.297564 0.399095 0.048 Uiso calc 1 . .
C C14B 0.22780(13) 0.49593(14) 0.34891(12) 0.0317(4) Uani d 1 . .
C C17B 0.40645(11) 0.57381(12) 0.27734(10) 0.0204(4) Uani d 1 . .
C C18B 0.41311(12) 0.51382(13) 0.21751(10) 0.0235(4) Uani d 1 . .
H H18B 0.407494 0.446967 0.224204 0.028 Uiso calc 1 . .
C C19B 0.42785(12) 0.54948(13) 0.14796(10) 0.0247(4) Uani d 1 . .
H H19B 0.432202 0.507346 0.107685 0.030 Uiso calc 1 . .
C C20B 0.43611(11) 0.64698(13) 0.13795(10) 0.0231(4) Uani d 1 . .
C C21B 0.42916(11) 0.70792(12) 0.19706(10) 0.0231(4) Uani d 1 . .
H H21B 0.434268 0.774830 0.190398 0.028 Uiso calc 1 . .
C C22B 0.41482(12) 0.67106(12) 0.26552(10) 0.0220(4) Uani d 1 . .
H H22B 0.410556 0.713382 0.305688 0.026 Uiso calc 1 . .
C C23B 0.46826(19) 0.62980(17) 0.01175(12) 0.0469(6) Uani d 1 . .
H H23A 0.481787 0.668742 -0.031018 0.070 Uiso calc 1 . .
H H23B 0.416580 0.590883 0.001799 0.070 Uiso calc 1 . .
H H23C 0.517779 0.588112 0.022755 0.070 Uiso calc 1 . .
O O3B 0.2269(3) 0.5956(3) 0.3723(4) 0.0335(6) Uani d 0.432(8) A 1
C C15B 0.1402(3) 0.6417(4) 0.3742(3) 0.0372(7) Uani d 0.465(5) A 1
H H15A 0.138304 0.689695 0.413646 0.045 Uiso calc 0.465(5) A 1
H H15B 0.094562 0.593444 0.383626 0.045 Uiso calc 0.465(5) A 1
C C16B 0.1245(4) 0.6886(5) 0.3024(3) 0.0467(11) Uani d 0.465(5) A 1
H H16A 0.123933 0.640269 0.263942 0.070 Uiso calc 0.465(5) A 1
H H16B 0.171021 0.734776 0.292792 0.070 Uiso calc 0.465(5) A 1
H H16C 0.068246 0.721642 0.303351 0.070 Uiso calc 0.465(5) A 1
O O3C 0.21906(19) 0.5876(2) 0.3397(3) 0.0334(5) Uani d 0.568(8) A 2
C C15C 0.1290(2) 0.6186(3) 0.3293(3) 0.0363(7) Uani d 0.535(5) A 2
H H15C 0.107508 0.596737 0.281287 0.044 Uiso calc 0.535(5) A 2
H H15D 0.091485 0.590425 0.367375 0.044 Uiso calc 0.535(5) A 2
C C16C 0.1252(3) 0.7220(3) 0.3332(3) 0.0423(10) Uani d 0.535(5) A 2
H H16D 0.164743 0.749457 0.297027 0.063 Uiso calc 0.535(5) A 2
H H16E 0.142609 0.742950 0.381911 0.063 Uiso calc 0.535(5) A 2
H H16F 0.065517 0.743317 0.323217 0.063 Uiso calc 0.535(5) A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 0.00 0.1730
0.00 1.00 0.00 0.1570
0.00 0.00 -1.00 0.0320
0.00 0.00 1.00 0.0760
1.00 0.00 -1.00 0.0190
-1.00 0.00 1.00 0.0740
-1.00 0.00 -1.00 0.0440
1.00 0.00 1.00 0.0600
-1.00 -1.00 1.00 0.1290
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
C14A O3A C15A . . 117.37(14) ?
C20A O4A C23A . . 117.16(15) ?
C2A N1A H1A . . 119.1(14) ?
C9A N1A H1A . . 118.1(14) ?
C9A N1A C2A . . 122.74(15) ?
N1A C2A C13A . . 113.58(15) ?
C3A C2A N1A . . 119.53(15) ?
C3A C2A C13A . . 126.84(16) ?
C2A C3A C4A . . 121.22(15) ?
C2A C3A C14A . . 120.62(15) ?
C14A C3A C4A . . 118.09(15) ?
C3A C4A H4A . . 108.1 ?
C3A C4A C17A . . 111.21(14) ?
C10A C4A C3A . . 109.82(13) ?
C10A C4A H4A . . 108.1 ?
C10A C4A C17A . . 111.34(14) ?
C17A C4A H4A . . 108.1 ?
O1A C5A C6A . . 120.38(15) ?
O1A C5A C10A . . 120.86(16) ?
C10A C5A C6A . . 118.72(14) ?
C5A C6A H6AA . . 108.7 ?
C5A C6A H6AB . . 108.7 ?
C5A C6A C7A . . 114.27(14) ?
H6AA C6A H6AB . . 107.6 ?
C7A C6A H6AA . . 108.7 ?
C7A C6A H6AB . . 108.7 ?
C8A C7A C6A . . 107.72(13) ?
C8A C7A C12A . . 109.13(14) ?
C11A C7A C6A . . 109.63(14) ?
C11A C7A C8A . . 111.51(14) ?
C11A C7A C12A . . 109.35(14) ?
C12A C7A C6A . . 109.46(14) ?
C7A C8A H8AA . . 108.9 ?
C7A C8A H8AB . . 108.9 ?
H8AA C8A H8AB . . 107.7 ?
C9A C8A C7A . . 113.21(14) ?
C9A C8A H8AA . . 108.9 ?
C9A C8A H8AB . . 108.9 ?
N1A C9A C8A . . 116.70(14) ?
C10A C9A N1A . . 119.66(15) ?
C10A C9A C8A . . 123.56(15) ?
C5A C10A C4A . . 118.62(14) ?
C9A C10A C4A . . 121.53(15) ?
C9A C10A C5A . . 119.83(15) ?
C7A C11A H11D . . 109.5 ?
C7A C11A H11E . . 109.5 ?
C7A C11A H11F . . 109.5 ?
H11D C11A H11E . . 109.5 ?
H11D C11A H11F . . 109.5 ?
H11E C11A H11F . . 109.5 ?
C7A C12A H12D . . 109.5 ?
C7A C12A H12E . . 109.5 ?
C7A C12A H12F . . 109.5 ?
H12D C12A H12E . . 109.5 ?
H12D C12A H12F . . 109.5 ?
H12E C12A H12F . . 109.5 ?
C2A C13A H13D . . 109.5 ?
C2A C13A H13E . . 109.5 ?
C2A C13A H13F . . 109.5 ?
H13D C13A H13E . . 109.5 ?
H13D C13A H13F . . 109.5 ?
H13E C13A H13F . . 109.5 ?
O2A C14A O3A . . 122.52(16) ?
O2A C14A C3A . . 127.20(17) ?
O3A C14A C3A . . 110.28(14) ?
O3A C15A H15E . . 110.3 ?
O3A C15A H15F . . 110.3 ?
O3A C15A C16A . . 107.13(15) ?
H15E C15A H15F . . 108.5 ?
C16A C15A H15E . . 110.3 ?
C16A C15A H15F . . 110.3 ?
C15A C16A H16G . . 109.5 ?
C15A C16A H16H . . 109.5 ?
C15A C16A H16I . . 109.5 ?
H16G C16A H16H . . 109.5 ?
H16G C16A H16I . . 109.5 ?
H16H C16A H16I . . 109.5 ?
C18A C17A C4A . . 119.95(15) ?
C22A C17A C4A . . 122.03(15) ?
C22A C17A C18A . . 117.99(16) ?
C17A C18A H18A . . 119.5 ?
C19A C18A C17A . . 121.04(16) ?
C19A C18A H18A . . 119.5 ?
C18A C19A H19A . . 120.0 ?
C18A C19A C20A . . 120.08(17) ?
C20A C19A H19A . . 120.0 ?
O4A C20A C19A . . 115.63(16) ?
O4A C20A C21A . . 124.56(16) ?
C21A C20A C19A . . 119.81(16) ?
C20A C21A H21A . . 120.4 ?
C20A C21A C22A . . 119.13(16) ?
C22A C21A H21A . . 120.4 ?
C17A C22A C21A . . 121.92(17) ?
C17A C22A H22A . . 119.0 ?
C21A C22A H22A . . 119.0 ?
O4A C23A H23D . . 109.5 ?
O4A C23A H23E . . 109.5 ?
O4A C23A H23F . . 109.5 ?
H23D C23A H23E . . 109.5 ?
H23D C23A H23F . . 109.5 ?
H23E C23A H23F . . 109.5 ?
C20B O4B C23B . . 117.05(15) ?
C2B N1B H1B . . 118.7(15) ?
C9B N1B H1B . . 117.1(15) ?
C9B N1B C2B . . 122.57(15) ?
N1B C2B C13B . . 112.90(15) ?
C3B C2B N1B . . 119.68(16) ?
C3B C2B C13B . . 127.41(17) ?
C2B C3B C4B . . 121.67(15) ?
C2B C3B C14B . . 118.97(17) ?
C14B C3B C4B . . 119.29(15) ?
C3B C4B H4B . . 107.9 ?
C3B C4B C17B . . 111.84(15) ?
C10B C4B C3B . . 110.35(14) ?
C10B C4B H4B . . 107.9 ?
C10B C4B C17B . . 110.91(14) ?
C17B C4B H4B . . 107.9 ?
O1B C5B C6B . . 119.96(16) ?
O1B C5B C10B . . 120.96(16) ?
C10B C5B C6B . . 119.02(15) ?
C5B C6B H6BA . . 108.5 ?
C5B C6B H6BB . . 108.5 ?
C5B C6B C7B . . 115.26(15) ?
H6BA C6B H6BB . . 107.5 ?
C7B C6B H6BA . . 108.5 ?
C7B C6B H6BB . . 108.5 ?
C6B C7B C12B . . 109.67(16) ?
C8B C7B C6B . . 107.70(14) ?
C8B C7B C11B . . 110.52(15) ?
C8B C7B C12B . . 108.84(15) ?
C11B C7B C6B . . 110.43(15) ?
C11B C7B C12B . . 109.64(15) ?
C7B C8B H8BA . . 109.0 ?
C7B C8B H8BB . . 109.0 ?
H8BA C8B H8BB . . 107.8 ?
C9B C8B C7B . . 112.93(14) ?
C9B C8B H8BA . . 109.0 ?
C9B C8B H8BB . . 109.0 ?
N1B C9B C8B . . 115.97(15) ?
C10B C9B N1B . . 120.28(16) ?
C10B C9B C8B . . 123.67(16) ?
C5B C10B C4B . . 119.68(15) ?
C9B C10B C4B . . 121.19(15) ?
C9B C10B C5B . . 119.12(16) ?
C7B C11B H11A . . 109.5 ?
C7B C11B H11B . . 109.5 ?
C7B C11B H11C . . 109.5 ?
H11A C11B H11B . . 109.5 ?
H11A C11B H11C . . 109.5 ?
H11B C11B H11C . . 109.5 ?
C7B C12B H12A . . 109.5 ?
C7B C12B H12B . . 109.5 ?
C7B C12B H12C . . 109.5 ?
H12A C12B H12B . . 109.5 ?
H12A C12B H12C . . 109.5 ?
H12B C12B H12C . . 109.5 ?
C2B C13B H13A . . 109.5 ?
C2B C13B H13B . . 109.5 ?
C2B C13B H13C . . 109.5 ?
H13A C13B H13B . . 109.5 ?
H13A C13B H13C . . 109.5 ?
H13B C13B H13C . . 109.5 ?
O2B C14B C3B . . 126.73(18) ?
O2B C14B O3B . . 125.1(2) ?
O2B C14B O3C . . 117.4(2) ?
O3B C14B C3B . . 106.6(2) ?
O3C C14B C3B . . 114.9(2) ?
C18B C17B C4B . . 121.57(15) ?
C22B C17B C4B . . 120.71(16) ?
C22B C17B C18B . . 117.71(17) ?
C17B C18B H18B . . 119.3 ?
C17B C18B C19B . . 121.46(16) ?
C19B C18B H18B . . 119.3 ?
C18B C19B H19B . . 120.3 ?
C20B C19B C18B . . 119.46(17) ?
C20B C19B H19B . . 120.3 ?
O4B C20B C19B . . 124.77(17) ?
O4B C20B C21B . . 115.41(15) ?
C19B C20B C21B . . 119.81(17) ?
C20B C21B H21B . . 120.1 ?
C22B C21B C20B . . 119.77(16) ?
C22B C21B H21B . . 120.1 ?
C17B C22B H22B . . 119.1 ?
C21B C22B C17B . . 121.79(17) ?
C21B C22B H22B . . 119.1 ?
O4B C23B H23A . . 109.5 ?
O4B C23B H23B . . 109.5 ?
O4B C23B H23C . . 109.5 ?
H23A C23B H23B . . 109.5 ?
H23A C23B H23C . . 109.5 ?
H23B C23B H23C . . 109.5 ?
C14B O3B C15B . . 115.7(4) ?
O3B C15B H15A . . 110.0 ?
O3B C15B H15B . . 110.0 ?
O3B C15B C16B . . 108.4(5) ?
H15A C15B H15B . . 108.4 ?
C16B C15B H15A . . 110.0 ?
C16B C15B H15B . . 110.0 ?
C15B C16B H16A . . 109.5 ?
C15B C16B H16B . . 109.5 ?
C15B C16B H16C . . 109.5 ?
H16A C16B H16B . . 109.5 ?
H16A C16B H16C . . 109.5 ?
H16B C16B H16C . . 109.5 ?
C14B O3C C15C . . 114.0(3) ?
O3C C15C H15C . . 109.8 ?
O3C C15C H15D . . 109.8 ?
H15C C15C H15D . . 108.3 ?
C16C C15C O3C . . 109.2(4) ?
C16C C15C H15C . . 109.8 ?
C16C C15C H15D . . 109.8 ?
C15C C16C H16D . . 109.5 ?
C15C C16C H16E . . 109.5 ?
C15C C16C H16F . . 109.5 ?
H16D C16C H16E . . 109.5 ?
H16D C16C H16F . . 109.5 ?
H16E C16C H16F . . 109.5 ?
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
O1A C5A . 1.235(2) ?
O2A C14A . 1.210(2) ?
O3A C14A . 1.343(2) ?
O3A C15A . 1.449(2) ?
O4A C20A . 1.367(2) ?
O4A C23A . 1.424(2) ?
N1A H1A . 0.82(2) ?
N1A C2A . 1.386(2) ?
N1A C9A . 1.367(2) ?
C2A C3A . 1.354(2) ?
C2A C13A . 1.498(2) ?
C3A C4A . 1.522(2) ?
C3A C14A . 1.473(2) ?
C4A H4A . 1.0000 ?
C4A C10A . 1.513(2) ?
C4A C17A . 1.523(2) ?
C5A C6A . 1.507(2) ?
C5A C10A . 1.440(2) ?
C6A H6AA . 0.9900 ?
C6A H6AB . 0.9900 ?
C6A C7A . 1.538(2) ?
C7A C8A . 1.529(2) ?
C7A C11A . 1.526(2) ?
C7A C12A . 1.530(2) ?
C8A H8AA . 0.9900 ?
C8A H8AB . 0.9900 ?
C8A C9A . 1.498(2) ?
C9A C10A . 1.356(2) ?
C11A H11D . 0.9800 ?
C11A H11E . 0.9800 ?
C11A H11F . 0.9800 ?
C12A H12D . 0.9800 ?
C12A H12E . 0.9800 ?
C12A H12F . 0.9800 ?
C13A H13D . 0.9800 ?
C13A H13E . 0.9800 ?
C13A H13F . 0.9800 ?
C15A H15E . 0.9900 ?
C15A H15F . 0.9900 ?
C15A C16A . 1.499(3) ?
C16A H16G . 0.9800 ?
C16A H16H . 0.9800 ?
C16A H16I . 0.9800 ?
C17A C18A . 1.398(2) ?
C17A C22A . 1.377(2) ?
C18A H18A . 0.9500 ?
C18A C19A . 1.380(2) ?
C19A H19A . 0.9500 ?
C19A C20A . 1.390(3) ?
C20A C21A . 1.385(3) ?
C21A H21A . 0.9500 ?
C21A C22A . 1.395(3) ?
C22A H22A . 0.9500 ?
C23A H23D . 0.9800 ?
C23A H23E . 0.9800 ?
C23A H23F . 0.9800 ?
O1B C5B . 1.239(2) ?
O2B C14B . 1.205(2) ?
O4B C20B . 1.372(2) ?
O4B C23B . 1.424(3) ?
N1B H1B . 0.87(2) ?
N1B C2B . 1.387(2) ?
N1B C9B . 1.363(2) ?
C2B C3B . 1.350(2) ?
C2B C13B . 1.506(2) ?
C3B C4B . 1.518(2) ?
C3B C14B . 1.474(3) ?
C4B H4B . 1.0000 ?
C4B C10B . 1.518(2) ?
C4B C17B . 1.529(2) ?
C5B C6B . 1.513(3) ?
C5B C10B . 1.442(2) ?
C6B H6BA . 0.9900 ?
C6B H6BB . 0.9900 ?
C6B C7B . 1.530(3) ?
C7B C8B . 1.525(2) ?
C7B C11B . 1.528(3) ?
C7B C12B . 1.534(3) ?
C8B H8BA . 0.9900 ?
C8B H8BB . 0.9900 ?
C8B C9B . 1.500(2) ?
C9B C10B . 1.357(2) ?
C11B H11A . 0.9800 ?
C11B H11B . 0.9800 ?
C11B H11C . 0.9800 ?
C12B H12A . 0.9800 ?
C12B H12B . 0.9800 ?
C12B H12C . 0.9800 ?
C13B H13A . 0.9800 ?
C13B H13B . 0.9800 ?
C13B H13C . 0.9800 ?
C14B O3B . 1.464(5) ?
C14B O3C . 1.305(4) ?
C17B C18B . 1.389(3) ?
C17B C22B . 1.388(2) ?
C18B H18B . 0.9500 ?
C18B C19B . 1.392(3) ?
C19B H19B . 0.9500 ?
C19B C20B . 1.386(2) ?
C20B C21B . 1.387(3) ?
C21B H21B . 0.9500 ?
C21B C22B . 1.379(3) ?
C22B H22B . 0.9500 ?
C23B H23A . 0.9800 ?
C23B H23B . 0.9800 ?
C23B H23C . 0.9800 ?
O3B C15B . 1.480(5) ?
C15B H15A . 0.9900 ?
C15B H15B . 0.9900 ?
C15B C16B . 1.495(7) ?
C16B H16A . 0.9800 ?
C16B H16B . 0.9800 ?
C16B H16C . 0.9800 ?
O3C C15C . 1.461(4) ?
C15C H15C . 0.9900 ?
C15C H15D . 0.9900 ?
C15C C16C . 1.454(6) ?
C16C H16D . 0.9800 ?
C16C H16E . 0.9800 ?
C16C H16F . 0.9800 ?
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
N1A H1A O1B . 0.82(2) 2.02(2) 2.827(2) 167(2) yes
N1B H1B O1A 1_545 0.87(2) 1.95(2) 2.8167(19) 172(2) 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
O1A C5A C6A C7A . . . . 153.92(16) ?
O1A C5A C10A C4A . . . . -5.0(2) ?
O1A C5A C10A C9A . . . . 176.67(16) ?
O4A C20A C21A C22A . . . . -178.33(16) ?
N1A C2A C3A C4A . . . . -6.9(2) ?
N1A C2A C3A C14A . . . . 176.06(15) ?
N1A C9A C10A C4A . . . . 8.8(2) ?
N1A C9A C10A C5A . . . . -172.89(15) ?
C2A N1A C9A C8A . . . . -166.11(15) ?
C2A N1A C9A C10A . . . . 10.6(2) ?
C2A C3A C4A C10A . . . . 22.8(2) ?
C2A C3A C4A C17A . . . . -100.92(19) ?
C2A C3A C14A O2A . . . . -5.7(3) ?
C2A C3A C14A O3A . . . . 174.96(15) ?
C3A C4A C10A C5A . . . . 157.86(15) ?
C3A C4A C10A C9A . . . . -23.8(2) ?
C3A C4A C17A C18A . . . . 60.5(2) ?
C3A C4A C17A C22A . . . . -117.40(18) ?
C4A C3A C14A O2A . . . . 177.13(18) ?
C4A C3A C14A O3A . . . . -2.2(2) ?
C4A C17A C18A C19A . . . . -176.55(16) ?
C4A C17A C22A C21A . . . . 176.66(16) ?
C5A C6A C7A C8A . . . . 51.96(19) ?
C5A C6A C7A C11A . . . . -69.55(18) ?
C5A C6A C7A C12A . . . . 170.51(15) ?
C6A C5A C10A C4A . . . . 177.41(15) ?
C6A C5A C10A C9A . . . . -0.9(2) ?
C6A C7A C8A C9A . . . . -48.74(18) ?
C7A C8A C9A N1A . . . . -160.18(15) ?
C7A C8A C9A C10A . . . . 23.2(2) ?
C8A C9A C10A C4A . . . . -174.68(15) ?
C8A C9A C10A C5A . . . . 3.6(3) ?
C9A N1A C2A C3A . . . . -11.6(2) ?
C9A N1A C2A C13A . . . . 166.11(16) ?
C10A C4A C17A C18A . . . . -62.3(2) ?
C10A C4A C17A C22A . . . . 119.77(17) ?
C10A C5A C6A C7A . . . . -28.5(2) ?
C11A C7A C8A C9A . . . . 71.59(18) ?
C12A C7A C8A C9A . . . . -167.50(14) ?
C13A C2A C3A C4A . . . . 175.76(16) ?
C13A C2A C3A C14A . . . . -1.3(3) ?
C14A O3A C15A C16A . . . . 151.27(16) ?
C14A C3A C4A C10A . . . . -160.11(14) ?
C14A C3A C4A C17A . . . . 76.19(19) ?
C15A O3A C14A O2A . . . . 4.7(3) ?
C15A O3A C14A C3A . . . . -175.91(15) ?
C17A C4A C10A C5A . . . . -78.52(19) ?
C17A C4A C10A C9A . . . . 99.81(19) ?
C17A C18A C19A C20A . . . . -0.2(3) ?
C18A C17A C22A C21A . . . . -1.3(3) ?
C18A C19A C20A O4A . . . . 178.51(16) ?
C18A C19A C20A C21A . . . . -1.2(3) ?
C19A C20A C21A C22A . . . . 1.4(3) ?
C20A C21A C22A C17A . . . . -0.1(3) ?
C22A C17A C18A C19A . . . . 1.5(3) ?
C23A O4A C20A C19A . . . . 173.05(16) ?
C23A O4A C20A C21A . . . . -7.2(3) ?
O1B C5B C6B C7B . . . . -160.26(16) ?
O1B C5B C10B C4B . . . . 8.1(2) ?
O1B C5B C10B C9B . . . . -171.09(17) ?
O2B C14B O3B C15B . . . . -9.3(6) ?
O2B C14B O3C C15C . . . . 7.8(5) ?
O4B C20B C21B C22B . . . . -179.01(16) ?
N1B C2B C3B C4B . . . . 5.1(3) ?
N1B C2B C3B C14B . . . . -177.98(17) ?
N1B C9B C10B C4B . . . . -6.9(3) ?
N1B C9B C10B C5B . . . . 172.28(16) ?
C2B N1B C9B C8B . . . . 166.25(16) ?
C2B N1B C9B C10B . . . . -10.6(3) ?
C2B C3B C4B C10B . . . . -19.6(2) ?
C2B C3B C4B C17B . . . . 104.42(19) ?
C2B C3B C14B O2B . . . . -7.6(3) ?
C2B C3B C14B O3B . . . . 158.7(3) ?
C2B C3B C14B O3C . . . . -176.0(3) ?
C3B C4B C10B C5B . . . . -158.71(15) ?
C3B C4B C10B C9B . . . . 20.4(2) ?
C3B C4B C17B C18B . . . . -48.7(2) ?
C3B C4B C17B C22B . . . . 132.47(17) ?
C3B C14B O3B C15B . . . . -175.9(4) ?
C3B C14B O3C C15C . . . . 177.3(3) ?
C4B C3B C14B O2B . . . . 169.4(2) ?
C4B C3B C14B O3B . . . . -24.3(3) ?
C4B C3B C14B O3C . . . . 1.0(4) ?
C4B C17B C18B C19B . . . . -178.71(16) ?
C4B C17B C22B C21B . . . . 178.92(16) ?
C5B C6B C7B C8B . . . . -49.4(2) ?
C5B C6B C7B C11B . . . . 71.33(19) ?
C5B C6B C7B C12B . . . . -167.74(15) ?
C6B C5B C10B C4B . . . . -174.81(15) ?
C6B C5B C10B C9B . . . . 6.0(2) ?
C6B C7B C8B C9B . . . . 50.18(19) ?
C7B C8B C9B N1B . . . . 157.48(16) ?
C7B C8B C9B C10B . . . . -25.8(2) ?
C8B C9B C10B C4B . . . . 176.56(16) ?
C8B C9B C10B C5B . . . . -4.3(3) ?
C9B N1B C2B C3B . . . . 11.5(3) ?
C9B N1B C2B C13B . . . . -167.51(17) ?
C10B C4B C17B C18B . . . . 74.9(2) ?
C10B C4B C17B C22B . . . . -103.88(18) ?
C10B C5B C6B C7B . . . . 22.6(2) ?
C11B C7B C8B C9B . . . . -70.53(19) ?
C12B C7B C8B C9B . . . . 169.02(16) ?
C13B C2B C3B C4B . . . . -176.03(18) ?
C13B C2B C3B C14B . . . . 0.9(3) ?
C14B C3B C4B C10B . . . . 163.53(17) ?
C14B C3B C4B C17B . . . . -72.5(2) ?
C14B O3B C15B C16B . . . . -91.8(6) ?
C14B O3C C15C C16C . . . . 169.5(5) ?
C17B C4B C10B C5B . . . . 76.8(2) ?
C17B C4B C10B C9B . . . . -104.08(19) ?
C17B C18B C19B C20B . . . . 0.0(3) ?
C18B C17B C22B C21B . . . . 0.1(3) ?
C18B C19B C20B O4B . . . . 179.16(16) ?
C18B C19B C20B C21B . . . . -0.4(3) ?
C19B C20B C21B C22B . . . . 0.6(3) ?
C20B C21B C22B C17B . . . . -0.4(3) ?
C22B C17B C18B C19B . . . . 0.1(3) ?
C23B O4B C20B C19B . . . . -5.9(3) ?
C23B O4B C20B C21B . . . . 173.67(18) ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6938(8)
2 0.3062(8)

_cod_database_fobs_code 2244193
