#------------------------------------------------------------------------------
#$Date: 2019-11-26 08:42:42 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243092 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/32/4133260.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_4133260
loop_
_publ_author_name
'Yao, Huan'
'Ke, Hua'
'Zhang, Xiaobin'
'Pan, San-Jiang'
'Li, Ming-Shuang'
'Yang, Liu-Pan'
'Schreckenbach, Georg'
'Jiang, Wei'
_publ_section_title
;
 Molecular Recognition of Hydrophilic Molecules in Water by Combining the
 Hydrophobic Effect with Hydrogen Bonding.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13466
_journal_page_last               13477
_journal_paper_doi               10.1021/jacs.8b09157
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C66 H66 N2 O10, C4 H8 O2'
_chemical_formula_sum            'C70 H74 N2 O12'
_chemical_formula_weight         1123.30
_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_date             2017-08-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                111.697(4)
_cell_angle_beta                 112.056(5)
_cell_angle_gamma                96.412(4)
_cell_formula_units_Z            1
_cell_length_a                   11.6938(8)
_cell_length_b                   12.6480(10)
_cell_length_c                   13.6896(9)
_cell_measurement_reflns_used    5293
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      58.88
_cell_measurement_theta_min      3.90
_cell_volume                     1668.2(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10876
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        54.242
_diffrn_reflns_theta_max         54.242
_diffrn_reflns_theta_min         3.895
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0717 before and 0.0500 after correction. The Ratio of minimum to maximum transmission is 0.8834. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_description       block
_exptl_crystal_F_000             598
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.205
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.560
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         4026
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.572
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.1086
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3536
_refine_ls_wR_factor_ref         0.3736
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2971
_reflns_number_total             4026
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b09157_si_008.cif
_cod_data_source_block           p-1_a
_cod_database_code               4133260
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C36-C37 = C35-C34
 1.53 with sigma of 0.02
 O7-C36
 1.2 with sigma of 0.02
 O6-C35
 1.42 with sigma of 0.02
 O6-C36
 1.38 with sigma of 0.02
 C32B-C31B
 1.54 with sigma of 0.02
 C32A-C31A
 1.54 with sigma of 0.02
 C31B-C30
 1.54 with sigma of 0.02
 C30-C31A
 1.54 with sigma of 0.02
 C32A-C33A
 1.54 with sigma of 0.02
 C32B-C33B
 1.54 with sigma of 0.02
 O7-O6
 2.3 with sigma of 0.04
 C34-O6
 2.4 with sigma of 0.04
 C37-O7
 2.3 with sigma of 0.04
 C30-C32B
 2.54 with sigma of 0.04
 C30-C32A
 2.54 with sigma of 0.04
 C31B-C33B
 2.54 with sigma of 0.04
 C31A-C33A
 2.54 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C37 \\sim C34 \\sim O7 \\sim C36 \\sim O6 \\sim C35: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C32B) = Uanis(C33B)
Uanis(C32B) = Uanis(C32A)
Uanis(C32A) = Uanis(C33A)
Uanis(C32A) = Uanis(C33A) = Uanis(C32B) = Uanis(C33B)
4. Others
 Fixed Sof: H18a(0.5) H18b(0.5) H19a(0.5) H19b(0.5) H30a(0.5) H30b(0.5)
 H30c(0.5) H30d(0.5) C31A(0.5) H31a(0.5) H31b(0.5) C31B(0.5) H31c(0.5)
 H31d(0.5) C32A(0.5) H32a(0.5) H32b(0.5) C32B(0.5) H32c(0.5) H32d(0.5)
 C33A(0.5) H33a(0.5) H33b(0.5) H33c(0.5) C33B(0.5) H33d(0.5) H33e(0.5)
 H33f(0.5) O5A(0.5) O5B(0.5) C34(0.5) H34a(0.5) H34b(0.5) H34c(0.5) C35(0.5)
 H35a(0.5) H35b(0.5) C36(0.5) C37(0.5) H37a(0.5) H37b(0.5) H37c(0.5) O6(0.5)
 O7(0.5)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C14(H14a,H14b), C15(H15a,H15b), C16(H16a,H16b), C18(H18a,H18b),
 C19(H19a,H19b), C30(H30a,H30b), C30(H30c,H30d), C31A(H31a,H31b), C31B(H31c,
 H31d), C32A(H32a,H32b), C32B(H32c,H32d), C35(H35a,H35b)
5.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C10(H10), C11(H11), C23(H23), C24(H24), C28(H28), C29(H29),
 N1(H1a)
5.d Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C33A(H33a,H33b,H33c), C33B(H33d,H33e,H33f), C34(H34a,
 H34b,H34c), C37(H37a,H37b,H37c)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.36363(15) 0.84568(15) 0.91390(13) 0.0829(7) Uani 1 1 d . . . . .
H1 H 0.3690 0.8964 0.9923 0.099 Uiso 1 1 calc R . . . .
C2 C 0.27060(13) 0.87316(14) 0.82529(12) 0.0723(6) Uani 1 1 d . . . . .
H2A H 0.2972 0.9592 0.8477 0.087 Uiso 1 1 calc R . . . .
H2B H 0.1838 0.8522 0.8203 0.087 Uiso 1 1 calc R . . . .
C3 C 0.26776(12) 0.80084(12) 0.70688(12) 0.0624(5) Uani 1 1 d . . . . .
H3 H 0.2018 0.8122 0.6425 0.075 Uiso 1 1 calc R . . . .
C4 C 0.27427(13) 0.64106(13) 0.77241(11) 0.0654(6) Uani 1 1 d . . . . .
C5 C 0.26106(13) 0.52166(13) 0.75615(12) 0.0638(6) Uani 1 1 d . . . . .
H5 H 0.2858 0.5046 0.8219 0.077 Uiso 1 1 calc R . . . .
C6 C 0.21235(12) 0.43227(13) 0.64478(12) 0.0662(6) Uani 1 1 d . . . . .
H6 H 0.2065 0.3528 0.6337 0.079 Uiso 1 1 calc R . . . .
C7 C 0.17071(12) 0.45507(12) 0.54624(10) 0.0510(5) Uani 1 1 d . . . . .
C8 C 0.11953(11) 0.36142(12) 0.43201(10) 0.0537(5) Uani 1 1 d . . . . .
C9 C 0.07330(12) 0.38522(12) 0.33503(11) 0.0598(5) Uani 1 1 d . . . . .
C10 C 0.07463(12) 0.50259(12) 0.35106(12) 0.0581(5) Uani 1 1 d . . . . .
H10 H 0.0400 0.5186 0.2850 0.070 Uiso 1 1 calc R . . . .
C11 C 0.12679(11) 0.59315(12) 0.46358(11) 0.0560(5) Uani 1 1 d . . . . .
H11 H 0.1273 0.6717 0.4736 0.067 Uiso 1 1 calc R . . . .
C12 C 0.17963(11) 0.57444(11) 0.56488(11) 0.0526(5) Uani 1 1 d . . . . .
C13 C 0.23991(12) 0.67073(12) 0.68280(11) 0.0567(5) Uani 1 1 d . . . . .
C14 C -0.01913(16) 0.31647(16) 0.12473(12) 0.0804(7) Uani 1 1 d . . . . .
H14A H 0.0454 0.3823 0.1347 0.097 Uiso 1 1 calc R . . . .
H14B H -0.0987 0.3404 0.1170 0.097 Uiso 1 1 calc R . . . .
C15 C -0.04787(14) 0.20569(15) 0.01648(13) 0.0775(7) Uani 1 1 d . . . . .
H15A H -0.0993 0.2156 -0.0540 0.093 Uiso 1 1 calc R . . . .
H15B H -0.1011 0.1381 0.0151 0.093 Uiso 1 1 calc R . . . .
C16 C 0.07056(16) 0.17590(16) 0.00921(13) 0.0832(7) Uani 1 1 d . . . . .
H16A H 0.1218 0.1647 0.0790 0.100 Uiso 1 1 calc R . . . .
H16B H 0.1243 0.2433 0.0107 0.100 Uiso 1 1 calc R . . . .
C17 C 0.03706(17) 0.06327(16) -0.10254(14) 0.0887(8) Uani 1 1 d . . . . .
H17A H -0.0126 0.0744 -0.1719 0.133 Uiso 1 1 calc GR . . . .
H17B H -0.0143 -0.0041 -0.1034 0.133 Uiso 1 1 calc GR . . . .
H17C H 0.1167 0.0474 -0.1040 0.133 Uiso 1 1 calc GR . . . .
C18 C 0.11849(12) 0.23630(12) 0.41355(12) 0.0610(5) Uani 1 1 d . . . . .
H18A H 0.0920 0.2188 0.4680 0.073 Uiso 0.5 1 calc R . P . .
H18B H 0.0551 0.1795 0.3319 0.073 Uiso 0.5 1 calc R . P . .
C19 C 0.27212(12) 0.11723(12) 0.42643(11) 0.0591(5) Uani 1 1 d . . . . .
H19A H 0.2121 0.0508 0.3485 0.071 Uiso 0.5 1 calc R . P . .
H19B H 0.2625 0.0987 0.4877 0.071 Uiso 0.5 1 calc R . P . .
C20 C 0.50675(13) 0.86949(13) 0.82875(11) 0.0622(6) Uani 1 1 d . . . . .
C21 C 0.40414(11) 0.84277(11) 0.72103(11) 0.0545(5) Uani 1 1 d . . . . .
C22 C 0.43441(11) 0.85201(11) 0.63252(11) 0.0520(5) Uani 1 1 d . . . . .
C23 C 0.34071(13) 0.84181(12) 0.52509(13) 0.0631(6) Uani 1 1 d . . . . .
H23 H 0.2544 0.8342 0.5140 0.076 Uiso 1 1 calc R . . . .
C24 C 0.36735(13) 0.84232(12) 0.43770(12) 0.0630(5) Uani 1 1 d . . . . .
H24 H 0.3012 0.8362 0.3674 0.076 Uiso 1 1 calc R . . . .
C25 C 0.49447(12) 0.85202(12) 0.45152(12) 0.0581(5) Uani 1 1 d . . . . .
C26 C 0.59201(12) 0.87147(12) 0.55701(11) 0.0579(5) Uani 1 1 d . . . . .
C27 C 0.56297(11) 0.87337(11) 0.65018(11) 0.0523(5) Uani 1 1 d . . . . .
C28 C 0.66162(13) 0.89567(13) 0.76030(11) 0.0618(6) Uani 1 1 d . . . . .
H28 H 0.7486 0.9096 0.7727 0.074 Uiso 1 1 calc R . . . .
C29 C 0.63444(13) 0.89755(14) 0.84837(12) 0.0691(6) Uani 1 1 d . . . . .
H29 H 0.7024 0.9180 0.9237 0.083 Uiso 1 1 calc R . . . .
C30 C 0.42920(18) 0.81360(16) 0.24984(15) 0.0259(7) Uani 0.5 1 d D . P . .
H30A H 0.3858 0.8767 0.2513 0.031 Uiso 0.5 1 calc R . P A 1
H30B H 0.3639 0.7382 0.2208 0.031 Uiso 0.5 1 calc R . P A 1
H30C H 0.4686 0.8451 0.2098 0.031 Uiso 0.5 1 calc R . P B 2
H30D H 0.3651 0.8561 0.2596 0.031 Uiso 0.5 1 calc R . P B 2
C31A C 0.3553(3) 0.6816(3) 0.1661(3) 0.1026(16) Uani 0.5 1 d D . P C 2
H31A H 0.3040 0.6524 0.1993 0.123 Uiso 0.5 1 calc R . P C 2
H31B H 0.2940 0.6755 0.0897 0.123 Uiso 0.5 1 calc R . P C 2
C31B C 0.4928(3) 0.8002(2) 0.17454(19) 0.0776(12) Uani 0.5 1 d D . P C 1
H31C H 0.5644 0.8735 0.2107 0.093 Uiso 0.5 1 calc R . P C 1
H31D H 0.4304 0.7920 0.0975 0.093 Uiso 0.5 1 calc R . P C 1
C32A C 0.4377(3) 0.5998(3) 0.1432(3) 0.1016(9) Uani 0.5 1 d D . P C 2
H32A H 0.4764 0.6188 0.0964 0.122 Uiso 0.5 1 calc R . P C 2
H32B H 0.5091 0.6160 0.2196 0.122 Uiso 0.5 1 calc R . P C 2
C32B C 0.5459(3) 0.6949(3) 0.1540(3) 0.1016(9) Uani 0.5 1 d D . P C 1
H32C H 0.4761 0.6219 0.1227 0.122 Uiso 0.5 1 calc R . P C 1
H32D H 0.6138 0.7058 0.2300 0.122 Uiso 0.5 1 calc R . P C 1
C33A C 0.3647(4) 0.4689(3) 0.0788(3) 0.1016(9) Uani 0.5 1 d D . P C 2
H33A H 0.2858 0.4541 0.0094 0.152 Uiso 0.5 1 calc GR . P C 2
H33B H 0.3421 0.4453 0.1313 0.152 Uiso 0.5 1 calc GR . P C 2
H33C H 0.4189 0.4224 0.0539 0.152 Uiso 0.5 1 calc GR . P C 2
C33B C 0.6025(3) 0.6801(4) 0.0673(3) 0.1016(9) Uani 0.5 1 d D . P C 1
H33D H 0.5384 0.6781 -0.0049 0.152 Uiso 0.5 1 calc GR . P C 1
H33E H 0.6260 0.6056 0.0482 0.152 Uiso 0.5 1 calc GR . P C 1
H33F H 0.6796 0.7471 0.1030 0.152 Uiso 0.5 1 calc GR . P C 1
N1 N 0.24033(10) 0.22206(9) 0.43371(9) 0.0572(4) Uani 1 1 d . . . . .
H1A H 0.3016 0.2835 0.4524 0.069 Uiso 1 1 calc R . . . .
O1 O 0.32666(10) 0.72283(10) 0.89098(8) 0.0800(4) Uani 1 1 d . . . . .
O2 O 0.49103(9) 0.86910(10) 0.92308(8) 0.0801(4) Uani 1 1 d . . . . .
O3 O 0.03027(9) 0.29240(8) 0.22564(7) 0.0670(4) Uani 1 1 d . . . . .
O4 O 0.52721(9) 0.84479(9) 0.36365(8) 0.0758(4) Uani 1 1 d . . . . .
O5A O 0.03167(17) 0.16375(17) 0.40101(18) 0.0824(8) Uani 0.5 1 d . . P . .
O5B O 0.19513(18) 0.03034(16) 0.3902(2) 0.0874(9) Uani 0.5 1 d . . P . .
C34 C 0.4543(11) 0.6175(4) 0.2964(6) 0.314(5) Uani 0.5 1 d D U P D -1
H34A H 0.4897 0.6179 0.2419 0.472 Uiso 0.5 1 calc GR . P D -1
H34B H 0.5220 0.6632 0.3777 0.472 Uiso 0.5 1 calc GR . P D -1
H34C H 0.3833 0.6535 0.2844 0.472 Uiso 0.5 1 calc GR . P D -1
C35 C 0.4053(8) 0.4926(4) 0.2737(4) 0.258(2) Uani 0.5 1 d D U P D -1
H35A H 0.3104 0.4700 0.2284 0.309 Uiso 0.5 1 calc R . P D -1
H35B H 0.4363 0.4434 0.2194 0.309 Uiso 0.5 1 calc R . P D -1
C36 C 0.4858(9) 0.4962(5) 0.4786(4) 0.2448(18) Uani 0.5 1 d D U P D -1
C37 C 0.4723(5) 0.4314(4) 0.5503(3) 0.220(3) Uani 0.5 1 d D U P D -1
H37A H 0.5462 0.4005 0.5731 0.330 Uiso 0.5 1 calc GR . P D -1
H37B H 0.3925 0.3653 0.5025 0.330 Uiso 0.5 1 calc GR . P D -1
H37C H 0.4696 0.4869 0.6212 0.330 Uiso 0.5 1 calc GR . P D -1
O6 O 0.4283(5) 0.4543(4) 0.3584(3) 0.2571(15) Uani 0.5 1 d D U P D -1
O7 O 0.5690(3) 0.5865(2) 0.5390(3) 0.2188(13) Uani 0.5 1 d D U P 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 0.0181 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_
_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_3
C2 C1 H1 108.0 . .
O1 C1 H1 108.0 . .
O1 C1 C2 113.26(10) . .
O2 C1 H1 108.0 . .
O2 C1 C2 113.53(16) . .
O2 C1 O1 105.92(14) . .
C1 C2 H2A 110.1 . .
C1 C2 H2B 110.1 . .
C1 C2 C3 108.01(14) . .
H2A C2 H2B 108.4 . .
C3 C2 H2A 110.1 . .
C3 C2 H2B 110.1 . .
C2 C3 H3 111.3 . .
C2 C3 C21 106.59(9) . .
C13 C3 C2 107.83(15) . .
C13 C3 H3 111.3 . .
C13 C3 C21 108.41(12) . .
C21 C3 H3 111.3 . .
C13 C4 C5 123.28(12) . .
C13 C4 O1 124.24(15) . .
O1 C4 C5 112.47(15) . .
C4 C5 H5 120.5 . .
C6 C5 C4 118.94(16) . .
C6 C5 H5 120.5 . .
C5 C6 H6 119.3 . .
C5 C6 C7 121.43(16) . .
C7 C6 H6 119.3 . .
C6 C7 C8 120.53(14) . .
C6 C7 C12 118.33(11) . .
C8 C7 C12 121.13(14) . .
C7 C8 C18 120.69(14) . .
C9 C8 C7 119.67(14) . .
C9 C8 C18 119.60(11) . .
C8 C9 C10 120.25(11) . .
O3 C9 C8 117.77(13) . .
O3 C9 C10 121.97(14) . .
C9 C10 H10 120.4 . .
C11 C10 C9 119.12(15) . .
C11 C10 H10 120.4 . .
C10 C11 H11 118.6 . .
C10 C11 C12 122.80(15) . .
C12 C11 H11 118.6 . .
C7 C12 C13 120.62(14) . .
C11 C12 C7 116.87(10) . .
C11 C12 C13 122.51(14) . .
C4 C13 C3 120.57(11) . .
C4 C13 C12 117.08(14) . .
C12 C13 C3 122.33(14) . .
H14A C14 H14B 108.4 . .
C15 C14 H14A 110.0 . .
C15 C14 H14B 110.0 . .
O3 C14 H14A 110.0 . .
O3 C14 H14B 110.0 . .
O3 C14 C15 108.57(16) . .
C14 C15 H15A 108.8 . .
C14 C15 H15B 108.8 . .
C14 C15 C16 113.82(12) . .
H15A C15 H15B 107.7 . .
C16 C15 H15A 108.8 . .
C16 C15 H15B 108.8 . .
C15 C16 H16A 109.2 . .
C15 C16 H16B 109.2 . .
C15 C16 C17 112.12(12) . .
H16A C16 H16B 107.9 . .
C17 C16 H16A 109.2 . .
C17 C16 H16B 109.2 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17B 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C8 C18 H18A 109.6 . .
C8 C18 H18B 109.6 . .
H18A C18 H18B 108.1 . .
N1 C18 C8 110.41(12) . .
N1 C18 H18A 109.6 . .
N1 C18 H18B 109.6 . .
H19A C19 H19B 108.0 . .
C26 C19 H19A 109.4 2_666 .
C26 C19 H19B 109.4 2_666 .
N1 C19 H19A 109.4 . .
N1 C19 H19B 109.4 . .
N1 C19 C26 111.06(12) . 2_666
C29 C20 C21 122.05(16) . .
O2 C20 C21 123.34(14) . .
O2 C20 C29 114.61(12) . .
C20 C21 C3 116.73(15) . .
C20 C21 C22 117.46(13) . .
C22 C21 C3 125.77(11) . .
C23 C22 C21 123.19(13) . .
C27 C22 C21 120.06(12) . .
C27 C22 C23 116.74(15) . .
C22 C23 H23 118.3 . .
C24 C23 C22 123.43(14) . .
C24 C23 H23 118.3 . .
C23 C24 H24 120.3 . .
C23 C24 C25 119.35(13) . .
C25 C24 H24 120.3 . .
C26 C25 C24 120.14(16) . .
O4 C25 C24 122.76(12) . .
O4 C25 C26 117.09(14) . .
C25 C26 C19 120.89(15) . 2_666
C25 C26 C27 119.79(14) . .
C27 C26 C19 119.20(12) . 2_666
C22 C27 C26 120.05(12) . .
C22 C27 C28 118.97(15) . .
C28 C27 C26 120.98(13) . .
C27 C28 H28 119.5 . .
C29 C28 C27 121.08(14) . .
C29 C28 H28 119.5 . .
C20 C29 H29 120.0 . .
C28 C29 C20 119.94(13) . .
C28 C29 H29 120.0 . .
H30A C30 H30B 108.7 . .
H30C C30 H30D 107.0 . .
C31A C30 H30C 107.6 . .
C31A C30 H30D 107.6 . .
C31B C30 H30A 110.5 . .
C31B C30 H30B 110.5 . .
O4 C30 H30A 110.5 . .
O4 C30 H30B 110.5 . .
O4 C30 H30C 107.6 . .
O4 C30 H30D 107.6 . .
O4 C30 C31A 119.0(2) . .
O4 C30 C31B 106.23(17) . .
C30 C31A H31A 108.3 . .
C30 C31A H31B 108.3 . .
H31A C31A H31B 107.4 . .
C32A C31A C30 115.8(2) . .
C32A C31A H31A 108.3 . .
C32A C31A H31B 108.3 . .
C30 C31B H31C 108.8 . .
C30 C31B H31D 108.8 . .
C30 C31B C32B 114.0(3) . .
H31C C31B H31D 107.7 . .
C32B C31B H31C 108.8 . .
C32B C31B H31D 108.8 . .
C31A C32A H32A 108.7 . .
C31A C32A H32B 108.7 . .
H32A C32A H32B 107.6 . .
C33A C32A C31A 114.0(3) . .
C33A C32A H32A 108.7 . .
C33A C32A H32B 108.7 . .
C31B C32B H32C 109.3 . .
C31B C32B H32D 109.3 . .
C31B C32B C33B 111.6(3) . .
H32C C32B H32D 108.0 . .
C33B C32B H32C 109.3 . .
C33B C32B H32D 109.3 . .
C32A C33A H33A 109.5 . .
C32A C33A H33B 109.5 . .
C32A C33A H33C 109.5 . .
H33A C33A H33B 109.5 . .
H33A C33A H33C 109.5 . .
H33B C33A H33C 109.5 . .
C32B C33B H33D 109.5 . .
C32B C33B H33E 109.5 . .
C32B C33B H33F 109.5 . .
H33D C33B H33E 109.5 . .
H33D C33B H33F 109.5 . .
H33E C33B H33F 109.5 . .
C18 N1 C19 124.60(12) . .
C18 N1 H1A 117.7 . .
C19 N1 H1A 117.7 . .
C4 O1 C1 114.51(14) . .
C20 O2 C1 119.23(11) . .
C9 O3 C14 117.92(12) . .
C25 O4 C30 119.55(14) . .
H34A C34 H34B 109.5 . .
H34A C34 H34C 109.5 . .
H34B C34 H34C 109.5 . .
C35 C34 H34A 109.5 . .
C35 C34 H34B 109.5 . .
C35 C34 H34C 109.5 . .
C34 C35 H35A 106.0 . .
C34 C35 H35B 106.0 . .
H35A C35 H35B 106.3 . .
O6 C35 C34 125.1(4) . .
O6 C35 H35A 106.0 . .
O6 C35 H35B 106.0 . .
O6 C36 C37 128.3(5) . .
O7 C36 C37 110.9(4) . .
O7 C36 O6 120.1(6) . .
C36 C37 H37A 109.5 . .
C36 C37 H37B 109.5 . .
C36 C37 H37C 109.5 . .
H37A C37 H37B 109.5 . .
H37A C37 H37C 109.5 . .
H37B C37 H37C 109.5 . .
C35 O6 C36 141.3(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1 1.0000 .
C1 C2 1.477(2) .
C1 O1 1.445(2) .
C1 O2 1.434(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C2 C3 1.524(2) .
C3 H3 1.0000 .
C3 C13 1.524(2) .
C3 C21 1.538(2) .
C4 C5 1.424(2) .
C4 C13 1.346(2) .
C4 O1 1.3964(15) .
C5 H5 0.9500 .
C5 C6 1.3626(18) .
C6 H6 0.9500 .
C6 C7 1.402(2) .
C7 C8 1.4057(15) .
C7 C12 1.420(2) .
C8 C9 1.392(2) .
C8 C18 1.505(2) .
C9 C10 1.415(2) .
C9 O3 1.3697(14) .
C10 H10 0.9500 .
C10 C11 1.3749(16) .
C11 H11 0.9500 .
C11 C12 1.412(2) .
C12 C13 1.4443(15) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C14 C15 1.503(2) .
C14 O3 1.444(2) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C15 C16 1.504(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C16 C17 1.529(2) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C18 N1 1.3919(19) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C19 C26 1.500(2) 2_666
C19 N1 1.395(2) .
C20 C21 1.3931(17) .
C20 C29 1.392(2) .
C20 O2 1.373(2) .
C21 C22 1.423(2) .
C22 C23 1.413(2) .
C22 C27 1.4069(19) .
C23 H23 0.9500 .
C23 C24 1.347(3) .
C24 H24 0.9500 .
C24 C25 1.411(2) .
C25 C26 1.3727(19) .
C25 O4 1.369(2) .
C26 C19 1.500(2) 2_666
C26 C27 1.431(2) .
C27 C28 1.4106(18) .
C28 H28 0.9500 .
C28 C29 1.350(3) .
C29 H29 0.9500 .
C30 H30A 0.9900 .
C30 H30B 0.9900 .
C30 H30C 0.9900 .
C30 H30D 0.9900 .
C30 C31A 1.539(3) .
C30 C31B 1.456(4) .
C30 O4 1.4142(19) .
C31A H31A 0.9900 .
C31A H31B 0.9900 .
C31A C32A 1.518(5) .
C31B H31C 0.9900 .
C31B H31D 0.9900 .
C31B C32B 1.509(5) .
C32A H32A 0.9900 .
C32A H32B 0.9900 .
C32A C33A 1.513(4) .
C32B H32C 0.9900 .
C32B H32D 0.9900 .
C32B C33B 1.529(6) .
C33A H33A 0.9800 .
C33A H33B 0.9800 .
C33A H33C 0.9800 .
C33B H33D 0.9800 .
C33B H33E 0.9800 .
C33B H33F 0.9800 .
N1 H1A 0.8800 .
C34 H34A 0.9800 .
C34 H34B 0.9800 .
C34 H34C 0.9800 .
C34 C35 1.491(8) .
C35 H35A 0.9900 .
C35 H35B 0.9900 .
C35 O6 1.364(7) .
C36 C37 1.529(8) .
C36 O6 1.374(5) .
C36 O7 1.177(6) .
C37 H37A 0.9800 .
C37 H37B 0.9800 .
C37 H37C 0.9800 .
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
1 0.000 -0.698 -0.198 248.4 87.9
