#------------------------------------------------------------------------------
#$Date: 2023-11-24 10:38:49 +0200 (Fri, 24 Nov 2023) $
#$Revision: 287771 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/96/7119650.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7119650
loop_
_publ_author_name
'U. B. Rao Khandavilli'
'Matteo Lusi'
'Balakrishna R. Bhogala'
'Anita R. Maguire'
'Matthias Stein'
'Simon E. Lawrence'
_publ_section_title
;
 Diversity in a simple co-crystal: racemic and kryptoracemic behaviour
;
_journal_name_full               Chem.Commun.
_journal_page_first              8309
_journal_page_last               8312
_journal_paper_doi               10.1039/C6CC04148E
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration .
_chemical_formula_moiety         'C11 H15 N O, C7 H6 O3'
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_weight         315.36
_chemical_name_common            '3-Methyl-2-Phenylbutyramide, Salicylic acid'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2016-05-16 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.2716(15)
_cell_length_b                   21.2062(18)
_cell_length_c                   10.0994(9)
_cell_measurement_reflns_used    6603
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      24.8608
_cell_measurement_theta_min      2.2336
_cell_volume                     3484.9(5)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18028
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.328
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.196
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.151
_refine_ls_abs_structure_details
;
Flack x determined using 1951 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         6129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.2890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1507
_reflns_number_gt                4981
_reflns_number_total             6129
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc04148e2.cif
_cod_data_source_block           Form_I
_cod_database_code               7119650
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.38495(18) 0.44349(11) 0.1221(2) 0.0601(7) Uani d . . . 1 . .
H H1A 0.3652 0.481 0.1174 0.072 Uiso calc U . R 1 . .
H H1B 0.3886 0.4249 0.1976 0.072 Uiso calc U . R 1 . .
C C2 0.40945(18) 0.41447(12) 0.0141(3) 0.0472(6) Uani d . . . 1 . .
O O3 0.40492(14) 0.44016(9) -0.09738(19) 0.0557(5) Uani d . . . 1 . .
C C4 0.4458(2) 0.34918(13) 0.0307(3) 0.0532(7) Uani d . . . 1 . .
H H4 0.4271 0.3328 0.1162 0.064 Uiso calc U . R 1 . .
C C5 0.4163(2) 0.30291(14) -0.0773(3) 0.0640(9) Uani d . . . 1 . .
H H5 0.4367 0.318 -0.163 0.077 Uiso calc U . R 1 . .
C C6 0.3235(3) 0.30025(19) -0.0841(6) 0.0959(14) Uani d . . . 1 . .
H H6A 0.3023 0.2842 -0.0021 0.144 Uiso calc U . R 1 . .
H H6B 0.3072 0.273 -0.1554 0.144 Uiso calc U . R 1 . .
H H6C 0.3022 0.3419 -0.0992 0.144 Uiso calc U . R 1 . .
C C7 0.4507(3) 0.23707(16) -0.0544(5) 0.0873(13) Uani d . . . 1 . .
H H7A 0.4343 0.2224 0.0316 0.131 Uiso calc U . R 1 . .
H H7B 0.5096 0.2383 -0.0593 0.131 Uiso calc U . R 1 . .
H H7C 0.4299 0.2089 -0.1209 0.131 Uiso calc U . R 1 . .
C C8 0.5390(2) 0.35488(13) 0.0372(3) 0.0538(8) Uani d . . . 1 . .
C C9 0.5815(3) 0.32644(19) 0.1397(4) 0.0777(11) Uani d . . . 1 . .
H H9 0.5528 0.3049 0.2052 0.093 Uiso calc U . R 1 . .
C C10 0.6666(3) 0.3298(2) 0.1456(5) 0.0986(15) Uani d . . . 1 . .
H H10 0.6947 0.31 0.2141 0.118 Uiso calc U . R 1 . .
C C11 0.7095(3) 0.3625(2) 0.0501(5) 0.0905(13) Uani d . . . 1 . .
H H11 0.7665 0.3651 0.0546 0.109 Uiso calc U . R 1 . .
C C12 0.6681(3) 0.39109(18) -0.0513(4) 0.0776(11) Uani d . . . 1 . .
H H12 0.697 0.4133 -0.1156 0.093 Uiso calc U . R 1 . .
C C13 0.5828(2) 0.38695(14) -0.0584(4) 0.0617(8) Uani d . . . 1 . .
H H13 0.5551 0.406 -0.1283 0.074 Uiso calc U . R 1 . .
O O21 0.3590(2) 0.57794(11) 1.0658(2) 0.0860(9) Uani d . . . 1 . .
C C22 0.3622(2) 0.59730(14) 0.9525(3) 0.0600(8) Uani d . . . 1 . .
O O23 0.3724(2) 0.55897(10) 0.8514(2) 0.0759(7) Uani d . . . 1 . .
H H23 0.3739 0.5224 0.878 0.114 Uiso calc U . R 1 . .
C C24 0.3539(2) 0.66433(15) 0.9167(3) 0.0652(9) Uani d . . . 1 . .
C C25 0.3472(4) 0.68367(19) 0.7860(4) 0.1018(17) Uani d . . . 1 . .
H H25 0.346 0.6537 0.7188 0.122 Uiso calc U . R 1 . .
C C26 0.3424(4) 0.7468(2) 0.7545(5) 0.116(2) Uani d . . . 1 . .
H H26 0.3383 0.7594 0.6666 0.139 Uiso calc U . R 1 . .
C C27 0.3436(4) 0.79037(19) 0.8523(5) 0.1100(18) Uani d . . . 1 . .
H H27 0.342 0.833 0.8311 0.132 Uiso calc U . R 1 . .
C C28 0.3472(5) 0.77272(19) 0.9786(5) 0.138(3) Uani d . . . 1 . .
H H28 0.3471 0.8034 1.0444 0.165 Uiso calc U . R 1 . .
C C29 0.3510(4) 0.70914(19) 1.0149(4) 0.1102(19) Uani d . . . 1 . .
O O30 0.3539(6) 0.69386(17) 1.1426(3) 0.241(4) Uani d . . . 1 . .
H H30 0.3293 0.6606 1.1544 0.361 Uiso calc U . R 1 . .
N N31 0.3752(2) 0.39059(12) 0.6225(3) 0.0671(8) Uani d . . . 1 . .
H H31A 0.3577 0.3524 0.6191 0.081 Uiso calc U . R 1 . .
H H31B 0.38 0.4093 0.6977 0.081 Uiso calc U . R 1 . .
C C32 0.39470(19) 0.42034(13) 0.5133(3) 0.0513(7) Uani d . . . 1 . .
O O33 0.38870(17) 0.39493(10) 0.4021(2) 0.0645(6) Uani d . . . 1 . .
C C34 0.42834(19) 0.48652(13) 0.5286(3) 0.0503(7) Uani d . . . 1 . .
H H34 0.4073 0.503 0.6126 0.06 Uiso calc U . R 1 . .
C C35 0.39985(19) 0.53210(13) 0.4189(3) 0.0521(7) Uani d . . . 1 . .
H H35 0.425 0.5182 0.3356 0.063 Uiso calc U . R 1 . .
C C36 0.3071(2) 0.53082(19) 0.4002(5) 0.0829(11) Uani d . . . 1 . .
H H36A 0.2807 0.541 0.4825 0.124 Uiso calc U . R 1 . .
H H36B 0.2904 0.4895 0.3722 0.124 Uiso calc U . R 1 . .
H H36C 0.2916 0.5612 0.3343 0.124 Uiso calc U . R 1 . .
C C37 0.4295(3) 0.59927(15) 0.4460(4) 0.0741(10) Uani d . . . 1 . .
H H37A 0.4154 0.6259 0.3725 0.111 Uiso calc U . R 1 . .
H H37B 0.4881 0.5992 0.4576 0.111 Uiso calc U . R 1 . .
H H37C 0.4037 0.615 0.5248 0.111 Uiso calc U . R 1 . .
C C38 0.52081(19) 0.48264(14) 0.5412(3) 0.0554(8) Uani d . . . 1 . .
C C39 0.5662(2) 0.44862(16) 0.4502(5) 0.0749(11) Uani d . . . 1 . .
H H39 0.5401 0.4273 0.3818 0.09 Uiso calc U . R 1 . .
C C40 0.6515(3) 0.4466(2) 0.4619(7) 0.113(2) Uani d . . . 1 . .
H H40 0.6825 0.4238 0.4011 0.136 Uiso calc U . R 1 . .
C C41 0.6894(3) 0.4780(3) 0.5627(9) 0.136(3) Uani d . . . 1 . .
H H41 0.7463 0.4764 0.5707 0.163 Uiso calc U . R 1 . .
C C42 0.6441(4) 0.5121(4) 0.6523(7) 0.133(3) Uani d . . . 1 . .
H H42 0.6706 0.5338 0.72 0.159 Uiso calc U . R 1 . .
C C43 0.5597(3) 0.5145(2) 0.6431(4) 0.0874(13) Uani d . . . 1 . .
H H43 0.5292 0.5372 0.7047 0.105 Uiso calc U . R 1 . .
O O51 0.3872(3) 0.25429(12) 0.5651(3) 0.1145(13) Uani d . . . 1 . .
C C52 0.3845(3) 0.23540(16) 0.4514(4) 0.0735(10) Uani d . . . 1 . .
O O53 0.3767(2) 0.27394(11) 0.3510(2) 0.0908(9) Uani d . . . 1 . .
H H53 0.3857 0.3102 0.3756 0.136 Uiso calc U . R 1 . .
C C54 0.3907(2) 0.16843(15) 0.4164(4) 0.0657(9) Uani d . . . 1 . .
C C55 0.3760(3) 0.14760(17) 0.2876(4) 0.0810(11) Uani d . . . 1 . .
H H55 0.3606 0.1763 0.2226 0.097 Uiso calc U . R 1 . .
C C56 0.3843(3) 0.08439(17) 0.2558(4) 0.0895(13) Uani d . . . 1 . .
H H56 0.3747 0.0706 0.1698 0.107 Uiso calc U . R 1 . .
C C57 0.4068(2) 0.04217(17) 0.3530(5) 0.0789(11) Uani d . . . 1 . .
H H57 0.4133 -0.0002 0.3314 0.095 Uiso calc U . R 1 . .
C C58 0.4193(3) 0.06093(18) 0.4779(5) 0.0936(14) Uani d . . . 1 . .
H H58 0.4342 0.0317 0.5421 0.112 Uiso calc U . R 1 . .
C C59 0.4102(3) 0.12418(18) 0.5117(4) 0.0879(13) Uani d . . . 1 . .
O O60 0.4239(4) 0.14042(15) 0.6383(4) 0.175(3) Uani d . . . 1 . .
H H60 0.4267 0.1789 0.6442 0.263 Uiso calc U . R 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'
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'
H H 0.0000 0.0000 '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
C2 N1 H1A . . 120.0
C2 N1 H1B . . 120.0
H1A N1 H1B . . 120.0
O3 C2 N1 . . 121.6(2)
O3 C2 C4 . . 121.3(2)
N1 C2 C4 . . 117.1(2)
C2 C4 C8 . . 108.7(2)
C2 C4 C5 . . 112.4(2)
C8 C4 C5 . . 113.0(3)
C2 C4 H4 . . 107.5
C8 C4 H4 . . 107.5
C5 C4 H4 . . 107.5
C6 C5 C7 . . 109.9(3)
C6 C5 C4 . . 111.5(3)
C7 C5 C4 . . 111.1(3)
C6 C5 H5 . . 108.1
C7 C5 H5 . . 108.1
C4 C5 H5 . . 108.1
C5 C6 H6A . . 109.5
C5 C6 H6B . . 109.5
H6A C6 H6B . . 109.5
C5 C6 H6C . . 109.5
H6A C6 H6C . . 109.5
H6B C6 H6C . . 109.5
C5 C7 H7A . . 109.5
C5 C7 H7B . . 109.5
H7A C7 H7B . . 109.5
C5 C7 H7C . . 109.5
H7A C7 H7C . . 109.5
H7B C7 H7C . . 109.5
C13 C8 C9 . . 118.7(3)
C13 C8 C4 . . 121.6(3)
C9 C8 C4 . . 119.7(3)
C8 C9 C10 . . 120.5(4)
C8 C9 H9 . . 119.7
C10 C9 H9 . . 119.7
C11 C10 C9 . . 120.1(4)
C11 C10 H10 . . 119.9
C9 C10 H10 . . 119.9
C12 C11 C10 . . 119.9(4)
C12 C11 H11 . . 120.1
C10 C11 H11 . . 120.1
C11 C12 C13 . . 120.1(4)
C11 C12 H12 . . 120.0
C13 C12 H12 . . 120.0
C8 C13 C12 . . 120.7(3)
C8 C13 H13 . . 119.7
C12 C13 H13 . . 119.7
O21 C22 O23 . . 121.8(3)
O21 C22 C24 . . 123.5(3)
O23 C22 C24 . . 114.7(3)
C22 O23 H23 . . 109.5
C29 C24 C25 . . 118.7(3)
C29 C24 C22 . . 119.6(3)
C25 C24 C22 . . 121.7(3)
C26 C25 C24 . . 120.7(4)
C26 C25 H25 . . 119.6
C24 C25 H25 . . 119.6
C27 C26 C25 . . 119.6(4)
C27 C26 H26 . . 120.2
C25 C26 H26 . . 120.2
C28 C27 C26 . . 120.6(4)
C28 C27 H27 . . 119.7
C26 C27 H27 . . 119.7
C27 C28 C29 . . 121.6(4)
C27 C28 H28 . . 119.2
C29 C28 H28 . . 119.2
O30 C29 C24 . . 122.0(4)
O30 C29 C28 . . 119.4(4)
C24 C29 C28 . . 118.6(4)
C29 O30 H30 . . 109.5
C32 N31 H31A . . 120.0
C32 N31 H31B . . 120.0
H31A N31 H31B . . 120.0
O33 C32 N31 . . 122.0(3)
O33 C32 C34 . . 121.3(3)
N31 C32 C34 . . 116.6(2)
C38 C34 C32 . . 108.5(2)
C38 C34 C35 . . 113.2(2)
C32 C34 C35 . . 113.5(2)
C38 C34 H34 . . 107.1
C32 C34 H34 . . 107.1
C35 C34 H34 . . 107.1
C36 C35 C37 . . 110.6(3)
C36 C35 C34 . . 112.1(3)
C37 C35 C34 . . 111.1(3)
C36 C35 H35 . . 107.6
C37 C35 H35 . . 107.6
C34 C35 H35 . . 107.6
C35 C36 H36A . . 109.5
C35 C36 H36B . . 109.5
H36A C36 H36B . . 109.5
C35 C36 H36C . . 109.5
H36A C36 H36C . . 109.5
H36B C36 H36C . . 109.5
C35 C37 H37A . . 109.5
C35 C37 H37B . . 109.5
H37A C37 H37B . . 109.5
C35 C37 H37C . . 109.5
H37A C37 H37C . . 109.5
H37B C37 H37C . . 109.5
C39 C38 C43 . . 120.3(4)
C39 C38 C34 . . 120.3(3)
C43 C38 C34 . . 119.4(3)
C38 C39 C40 . . 119.5(5)
C38 C39 H39 . . 120.2
C40 C39 H39 . . 120.2
C41 C40 C39 . . 119.9(6)
C41 C40 H40 . . 120.1
C39 C40 H40 . . 120.1
C40 C41 C42 . . 120.4(5)
C40 C41 H41 . . 119.8
C42 C41 H41 . . 119.8
C41 C42 C43 . . 120.7(6)
C41 C42 H42 . . 119.7
C43 C42 H42 . . 119.7
C42 C43 C38 . . 119.2(6)
C42 C43 H43 . . 120.4
C38 C43 H43 . . 120.4
O51 C52 O53 . . 121.9(3)
O51 C52 C54 . . 123.0(3)
O53 C52 C54 . . 115.1(3)
C52 O53 H53 . . 109.5
C59 C54 C55 . . 118.3(3)
C59 C54 C52 . . 120.3(3)
C55 C54 C52 . . 121.3(3)
C56 C55 C54 . . 120.4(4)
C56 C55 H55 . . 119.8
C54 C55 H55 . . 119.8
C57 C56 C55 . . 119.3(4)
C57 C56 H56 . . 120.3
C55 C56 H56 . . 120.3
C58 C57 C56 . . 121.2(4)
C58 C57 H57 . . 119.4
C56 C57 H57 . . 119.4
C57 C58 C59 . . 120.1(4)
C57 C58 H58 . . 119.9
C59 C58 H58 . . 119.9
O60 C59 C54 . . 121.8(4)
O60 C59 C58 . . 117.6(4)
C54 C59 C58 . . 120.5(4)
C59 O60 H60 . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C2 . 1.315(4)
N1 H1A . 0.86
N1 H1B . 0.86
C2 O3 . 1.253(3)
C2 C4 . 1.515(4)
C4 C8 . 1.522(5)
C4 C5 . 1.544(4)
C4 H4 . 0.98
C5 C6 . 1.511(6)
C5 C7 . 1.522(5)
C5 H5 . 0.98
C6 H6A . 0.96
C6 H6B . 0.96
C6 H6C . 0.96
C7 H7A . 0.96
C7 H7B . 0.96
C7 H7C . 0.96
C8 C13 . 1.379(5)
C8 C9 . 1.383(5)
C9 C10 . 1.389(7)
C9 H9 . 0.93
C10 C11 . 1.377(7)
C10 H10 . 0.93
C11 C12 . 1.368(6)
C11 H11 . 0.93
C12 C13 . 1.393(5)
C12 H12 . 0.93
C13 H13 . 0.93
O21 C22 . 1.217(4)
C22 O23 . 1.315(4)
C22 C24 . 1.473(4)
O23 H23 . 0.82
C24 C29 . 1.374(5)
C24 C25 . 1.387(6)
C25 C26 . 1.379(6)
C25 H25 . 0.93
C26 C27 . 1.352(7)
C26 H26 . 0.93
C27 C28 . 1.331(7)
C27 H27 . 0.93
C28 C29 . 1.399(6)
C28 H28 . 0.93
C29 O30 . 1.330(5)
O30 H30 . 0.82
N31 C32 . 1.310(4)
N31 H31A . 0.86
N31 H31B . 0.86
C32 O33 . 1.249(3)
C32 C34 . 1.514(4)
C34 C38 . 1.512(4)
C34 C35 . 1.542(4)
C34 H34 . 0.98
C35 C36 . 1.521(5)
C35 C37 . 1.529(4)
C35 H35 . 0.98
C36 H36A . 0.96
C36 H36B . 0.96
C36 H36C . 0.96
C37 H37A . 0.96
C37 H37B . 0.96
C37 H37C . 0.96
C38 C39 . 1.383(5)
C38 C43 . 1.384(5)
C39 C40 . 1.393(6)
C39 H39 . 0.93
C40 C41 . 1.365(10)
C40 H40 . 0.93
C41 C42 . 1.374(10)
C41 H41 . 0.93
C42 C43 . 1.376(8)
C42 H42 . 0.93
C43 H43 . 0.93
O51 C52 . 1.216(4)
C52 O53 . 1.309(4)
C52 C54 . 1.467(5)
O53 H53 . 0.82
C54 C59 . 1.381(5)
C54 C55 . 1.394(5)
C55 C56 . 1.385(5)
C55 H55 . 0.93
C56 C57 . 1.378(6)
C56 H56 . 0.93
C57 C58 . 1.338(6)
C57 H57 . 0.93
C58 C59 . 1.392(6)
C58 H58 . 0.93
C59 O60 . 1.343(5)
O60 H60 . 0.82
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
O3 C2 C4 C8 . . . . 82.6(3)
N1 C2 C4 C8 . . . . -95.6(3)
O3 C2 C4 C5 . . . . -43.3(4)
N1 C2 C4 C5 . . . . 138.4(3)
C2 C4 C5 C6 . . . . -54.4(4)
C8 C4 C5 C6 . . . . -178.0(3)
C2 C4 C5 C7 . . . . -177.4(3)
C8 C4 C5 C7 . . . . 59.1(4)
C2 C4 C8 C13 . . . . -52.2(4)
C5 C4 C8 C13 . . . . 73.3(4)
C2 C4 C8 C9 . . . . 128.9(3)
C5 C4 C8 C9 . . . . -105.5(3)
C13 C8 C9 C10 . . . . -0.4(5)
C4 C8 C9 C10 . . . . 178.4(4)
C8 C9 C10 C11 . . . . 1.0(7)
C9 C10 C11 C12 . . . . -0.6(7)
C10 C11 C12 C13 . . . . -0.3(6)
C9 C8 C13 C12 . . . . -0.5(5)
C4 C8 C13 C12 . . . . -179.4(3)
C11 C12 C13 C8 . . . . 0.9(6)
O21 C22 C24 C29 . . . . 7.1(7)
O23 C22 C24 C29 . . . . -173.7(5)
O21 C22 C24 C25 . . . . -171.5(5)
O23 C22 C24 C25 . . . . 7.7(6)
C29 C24 C25 C26 . . . . 3.6(9)
C22 C24 C25 C26 . . . . -177.7(5)
C24 C25 C26 C27 . . . . -0.5(10)
C25 C26 C27 C28 . . . . -1.9(11)
C26 C27 C28 C29 . . . . 1.0(12)
C25 C24 C29 O30 . . . . 177.4(7)
C22 C24 C29 O30 . . . . -1.2(10)
C25 C24 C29 C28 . . . . -4.4(9)
C22 C24 C29 C28 . . . . 176.9(6)
C27 C28 C29 O30 . . . . -179.6(8)
C27 C28 C29 C24 . . . . 2.2(12)
O33 C32 C34 C38 . . . . -87.5(4)
N31 C32 C34 C38 . . . . 90.1(3)
O33 C32 C34 C35 . . . . 39.3(4)
N31 C32 C34 C35 . . . . -143.1(3)
C38 C34 C35 C36 . . . . 175.0(3)
C32 C34 C35 C36 . . . . 50.7(4)
C38 C34 C35 C37 . . . . -60.6(3)
C32 C34 C35 C37 . . . . 175.1(3)
C32 C34 C38 C39 . . . . 50.7(4)
C35 C34 C38 C39 . . . . -76.3(4)
C32 C34 C38 C43 . . . . -130.6(3)
C35 C34 C38 C43 . . . . 102.4(3)
C43 C38 C39 C40 . . . . 0.1(5)
C34 C38 C39 C40 . . . . 178.7(3)
C38 C39 C40 C41 . . . . 0.0(7)
C39 C40 C41 C42 . . . . -0.4(8)
C40 C41 C42 C43 . . . . 0.8(9)
C41 C42 C43 C38 . . . . -0.7(8)
C39 C38 C43 C42 . . . . 0.3(6)
C34 C38 C43 C42 . . . . -178.4(4)
O51 C52 C54 C59 . . . . -8.1(7)
O53 C52 C54 C59 . . . . 171.1(4)
O51 C52 C54 C55 . . . . 171.0(5)
O53 C52 C54 C55 . . . . -9.7(6)
C59 C54 C55 C56 . . . . -2.6(7)
C52 C54 C55 C56 . . . . 178.3(4)
C54 C55 C56 C57 . . . . 0.3(7)
C55 C56 C57 C58 . . . . 1.2(7)
C56 C57 C58 C59 . . . . -0.3(7)
C55 C54 C59 O60 . . . . -178.9(5)
C52 C54 C59 O60 . . . . 0.2(8)
C55 C54 C59 C58 . . . . 3.4(7)
C52 C54 C59 C58 . . . . -177.4(4)
C57 C58 C59 O60 . . . . -179.8(6)
C57 C58 C59 C54 . . . . -2.0(8)
