#------------------------------------------------------------------------------
#$Date: 2024-12-16 19:33:52 +0200 (Mon, 16 Dec 2024) $
#$Revision: 296876 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/06/7130651.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_7130651
loop_
_publ_author_name
'Debnath, Snehasish'
'Chatterjee, Pabitra B.'
_publ_section_title
;
 Enantiopure chiroptical probes for circular dichroism and absorbance
 based detection of nerve gas simulants.
;
_journal_issue                   64
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9006
_journal_page_last               9009
_journal_paper_doi               10.1039/d2cc03392e
_journal_volume                  58
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H29 N O3, 1/3(H2 O)'
_chemical_formula_sum            'C21 H29.66667 N O3.33333'
_chemical_formula_weight         349.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-06-08
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-06-15 deposited with the CCDC.	2022-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.6730(10)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   10.8179(2)
_cell_length_b                   20.9974(5)
_cell_length_c                   13.8796(2)
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      33.47
_cell_measurement_theta_min      2.26
_cell_volume                     2909.08(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23464
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.94
_diffrn_source                   'MICRO FOCUS TUBE'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.6987
_exptl_absorpt_correction_T_min  0.5926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.175
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     715
_refine_ls_number_reflns         9607
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0428P)²+0.5371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0902
_reflns_number_gt                9057
_reflns_number_total             9607
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc03392e5.cif
_cod_data_source_block           SND406ligand2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C63 H89 N3 O10'
_cod_original_formula_weight         1048.37
_cod_original_formula_moiety         '3(C21 H29 N O3), H2 O'
_cod_original_formula_units_Z            2
_cod_database_code               7130651
_olex2_refinement_description
;
1. Restrained distances
 H2O-O10 = H1O-O10
 0.82 with sigma of 0.02
2.a Ternary CH refined with riding coordinates:
 C10(H10), C31(H31), C52(H52)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B), C30(H30A,H30B), C33(H33A,H33B),
 C34(H34A,H34B), C51(H51A,H51B), C54(H54A,H54B), C55(H55A,H55B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C17(H17), C19(H19), C25(H25), C27(H27), C38(H38), C40(H40),
 C46(H46), C48(H48), C59(H59), C61(H61)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C20(H20A,H20B,H20C),
 C21(H21A,H21B,H21C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C32(H32A,H32B,
 H32C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C49(H49A,H49B,H49C), C50(H50A,
 H50B,H50C), C53(H53A,H53B,H53C), C62(H62A,H62B,H62C), C63(H63A,H63B,H63C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4A), O5(H5), O6(H6A), O7(H7), O8(H8), O9(H9)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
C C1 0.1242(2) 0.24906(13) 0.80138(18) 0.0184(5) Uani d . . . 1 . .
C C2 0.2107(2) 0.29466(12) 0.86581(18) 0.0180(5) Uani d . . . 1 . .
C C3 0.2050(2) 0.31160(12) 0.96158(18) 0.0190(5) Uani d . . . 1 . .
C C4 0.1084(2) 0.28184(13) 0.98967(19) 0.0194(5) Uani d . . . 1 . .
H H4 0.103827 0.292461 1.054739 0.023 Uiso calc U . R 1 . .
C C5 0.0184(2) 0.23715(12) 0.92615(19) 0.0189(5) Uani d . . . 1 . .
C C6 0.0279(2) 0.22161(12) 0.83175(19) 0.0177(5) Uani d . . . 1 . .
H H6 -0.032851 0.191522 0.786995 0.021 Uiso calc U . R 1 . .
C C7 0.3010(3) 0.36035(14) 1.0294(2) 0.0258(6) Uani d . . . 1 . .
H H7A 0.287047 0.365168 1.094693 0.039 Uiso calc U . R 1 . .
H H7B 0.285516 0.401293 0.992712 0.039 Uiso calc U . R 1 . .
H H7C 0.393201 0.346385 1.044986 0.039 Uiso calc U . R 1 . .
C C8 -0.0861(3) 0.20573(14) 0.9574(2) 0.0236(6) Uani d . . . 1 . .
H H8A -0.175196 0.213099 0.903118 0.035 Uiso calc U . R 1 . .
H H8B -0.082264 0.223858 1.023573 0.035 Uiso calc U . R 1 . .
H H8C -0.068765 0.15984 0.965816 0.035 Uiso calc U . R 1 . .
C C9 0.1395(3) 0.22955(12) 0.70195(19) 0.0200(5) Uani d . . . 1 . .
H H9A 0.221829 0.203661 0.719518 0.024 Uiso calc U . R 1 . .
H H9B 0.062289 0.202751 0.659806 0.024 Uiso calc U . R 1 . .
C C10 0.0207(3) 0.32282(15) 0.60110(19) 0.0245(6) Uani d . . . 1 . .
H H10 -0.008311 0.327072 0.661048 0.029 Uiso calc U . R 1 . .
C C11 -0.0947(3) 0.29098(18) 0.5122(2) 0.0348(7) Uani d . . . 1 . .
H H11A -0.073402 0.289163 0.449756 0.052 Uiso calc U . R 1 . .
H H11B -0.176943 0.315681 0.497006 0.052 Uiso calc U . R 1 . .
H H11C -0.107682 0.24768 0.532989 0.052 Uiso calc U . R 1 . .
C C12 0.0432(3) 0.38967(15) 0.5702(2) 0.0305(6) Uani d . . . 1 . .
H H12A 0.085051 0.387134 0.518173 0.037 Uiso calc U . R 1 . .
H H12B -0.044553 0.411107 0.536501 0.037 Uiso calc U . R 1 . .
C C13 0.1916(3) 0.26401(13) 0.55571(19) 0.0205(5) Uani d . . . 1 . .
H H13A 0.16346 0.295829 0.498675 0.025 Uiso calc U . R 1 . .
H H13B 0.14782 0.223037 0.526606 0.025 Uiso calc U . R 1 . .
C C14 0.3421(2) 0.25586(13) 0.59668(18) 0.0193(5) Uani d . . . 1 . .
C C15 0.4224(3) 0.31017(14) 0.61140(19) 0.0226(5) Uani d . . . 1 . .
C C16 0.5620(3) 0.30557(14) 0.6486(2) 0.0266(6) Uani d . . . 1 . .
C C17 0.6194(3) 0.24549(15) 0.6733(2) 0.0267(6) Uani d . . . 1 . .
H H17 0.714246 0.24185 0.700286 0.032 Uiso calc U . R 1 . .
C C18 0.5430(3) 0.19051(14) 0.65995(19) 0.0248(6) Uani d . . . 1 . .
C C19 0.4043(3) 0.19697(14) 0.62152(19) 0.0218(5) Uani d . . . 1 . .
H H19 0.350596 0.159875 0.612004 0.026 Uiso calc U . R 1 . .
C C20 0.6458(3) 0.36452(17) 0.6584(3) 0.0390(7) Uani d . . . 1 . .
H H20A 0.6237 0.383445 0.589216 0.059 Uiso calc U . R 1 . .
H H20B 0.740964 0.353078 0.688257 0.059 Uiso calc U . R 1 . .
H H20C 0.627134 0.395338 0.70411 0.059 Uiso calc U . R 1 . .
C C21 0.6100(3) 0.12647(15) 0.6870(2) 0.0334(7) Uani d . . . 1 . .
H H21A 0.63646 0.112289 0.63036 0.05 Uiso calc U . R 1 . .
H H21B 0.547624 0.095588 0.696267 0.05 Uiso calc U . R 1 . .
H H21C 0.689735 0.12983 0.751827 0.05 Uiso calc U . R 1 . .
C C22 0.7671(2) 0.52783(13) 1.07829(17) 0.0184(5) Uani d . . . 1 . .
C C23 0.7170(2) 0.46836(13) 1.03674(19) 0.0191(5) Uani d . . . 1 . .
C C24 0.8017(3) 0.42231(13) 1.02101(19) 0.0218(5) Uani d . . . 1 . .
C C25 0.9367(3) 0.43742(13) 1.04950(19) 0.0213(5) Uani d . . . 1 . .
H H25 0.994699 0.406358 1.039716 0.026 Uiso calc U . R 1 . .
C C26 0.9897(2) 0.49590(13) 1.09148(18) 0.0195(5) Uani d . . . 1 . .
C C27 0.9027(2) 0.54100(13) 1.10428(17) 0.0189(5) Uani d . . . 1 . .
H H27 0.936541 0.58177 1.131411 0.023 Uiso calc U . R 1 . .
C C28 0.7459(3) 0.35886(14) 0.9734(2) 0.0303(6) Uani d . . . 1 . .
H H28A 0.817863 0.332706 0.967833 0.045 Uiso calc U . R 1 . .
H H28B 0.676265 0.365475 0.903691 0.045 Uiso calc U . R 1 . .
H H28C 0.7071 0.337109 1.01765 0.045 Uiso calc U . R 1 . .
C C29 1.1374(2) 0.51093(13) 1.1244(2) 0.0246(6) Uani d . . . 1 . .
H H29A 1.148089 0.555503 1.108156 0.037 Uiso calc U . R 1 . .
H H29B 1.176186 0.483118 1.086689 0.037 Uiso calc U . R 1 . .
H H29C 1.183447 0.503873 1.199691 0.037 Uiso calc U . R 1 . .
C C30 0.6769(2) 0.57832(12) 1.09433(18) 0.0175(5) Uani d . . . 1 . .
H H30A 0.625331 0.559724 1.132857 0.021 Uiso calc U . R 1 . .
H H30B 0.732429 0.613436 1.136943 0.021 Uiso calc U . R 1 . .
C C31 0.4613(2) 0.63493(12) 0.99615(19) 0.0181(5) Uani d . . . 1 . .
H H31 0.406878 0.649784 0.923642 0.022 Uiso calc U . R 1 . .
C C32 0.4856(3) 0.69239(14) 1.0676(2) 0.0253(6) Uani d . . . 1 . .
H H32A 0.539556 0.679635 1.139518 0.038 Uiso calc U . R 1 . .
H H32B 0.39951 0.709373 1.06388 0.038 Uiso calc U . R 1 . .
H H32C 0.533387 0.725225 1.045372 0.038 Uiso calc U . R 1 . .
C C33 0.3764(2) 0.58608(13) 1.02556(19) 0.0204(5) Uani d . . . 1 . .
H H33A 0.414122 0.580803 1.102379 0.024 Uiso calc U . R 1 . .
H H33B 0.284381 0.603096 1.004988 0.024 Uiso calc U . R 1 . .
C C34 0.6538(2) 0.64534(12) 0.94469(18) 0.0164(5) Uani d . . . 1 . .
H H34A 0.741727 0.626233 0.95509 0.02 Uiso calc U . R 1 . .
H H34B 0.67042 0.687394 0.979635 0.02 Uiso calc U . R 1 . .
C C35 0.5741(2) 0.65438(12) 0.82926(19) 0.0170(5) Uani d . . . 1 . .
C C36 0.5080(2) 0.60256(13) 0.76816(19) 0.0190(5) Uani d . . . 1 . .
C C37 0.4415(3) 0.60803(14) 0.6596(2) 0.0234(6) Uani d . . . 1 . .
C C38 0.4430(3) 0.66664(15) 0.61495(19) 0.0239(6) Uani d . . . 1 . .
H H38 0.399622 0.670788 0.541319 0.029 Uiso calc U . R 1 . .
C C39 0.5053(2) 0.71987(14) 0.6731(2) 0.0221(6) Uani d . . . 1 . .
C C40 0.5705(2) 0.71232(13) 0.78072(19) 0.0177(5) Uani d . . . 1 . .
H H40 0.613729 0.74802 0.822015 0.021 Uiso calc U . R 1 . .
C C41 0.3726(3) 0.55069(16) 0.5960(2) 0.0363(7) Uani d . . . 1 . .
H H41A 0.33543 0.561938 0.521703 0.054 Uiso calc U . R 1 . .
H H41B 0.300128 0.536869 0.616981 0.054 Uiso calc U . R 1 . .
H H41C 0.437531 0.516044 0.607895 0.054 Uiso calc U . R 1 . .
C C42 0.4999(3) 0.78361(15) 0.6219(2) 0.0302(6) Uani d . . . 1 . .
H H42A 0.551994 0.781784 0.577763 0.045 Uiso calc U . R 1 . .
H H42B 0.537606 0.816283 0.675731 0.045 Uiso calc U . R 1 . .
H H42C 0.406605 0.794235 0.578878 0.045 Uiso calc U . R 1 . .
C C43 0.7829(3) 0.55843(13) 0.51559(19) 0.0218(5) Uani d . . . 1 . .
C C44 0.8965(3) 0.56145(13) 0.49107(19) 0.0240(6) Uani d . . . 1 . .
C C45 0.9003(3) 0.52969(15) 0.4039(2) 0.0290(6) Uani d . . . 1 . .
C C46 0.7871(3) 0.49592(14) 0.3412(2) 0.0319(7) Uani d . . . 1 . .
H H46 0.787741 0.475416 0.280419 0.038 Uiso calc U . R 1 . .
C C47 0.6734(3) 0.49103(14) 0.3641(2) 0.0320(7) Uani d . . . 1 . .
C C48 0.6742(3) 0.52213(14) 0.4530(2) 0.0282(6) Uani d . . . 1 . .
H H48 0.598443 0.518418 0.471333 0.034 Uiso calc U . R 1 . .
C C49 1.0252(3) 0.53248(19) 0.3810(2) 0.0398(8) Uani d . . . 1 . .
H H49A 1.052544 0.576971 0.380947 0.06 Uiso calc U . R 1 . .
H H49B 1.007468 0.513481 0.312468 0.06 Uiso calc U . R 1 . .
H H49C 1.097066 0.508801 0.434739 0.06 Uiso calc U . R 1 . .
C C50 0.5513(4) 0.45413(17) 0.2938(3) 0.0456(8) Uani d . . . 1 . .
H H50A 0.495595 0.481564 0.236332 0.068 Uiso calc U . R 1 . .
H H50B 0.499375 0.440151 0.334225 0.068 Uiso calc U . R 1 . .
H H50C 0.580181 0.416863 0.265358 0.068 Uiso calc U . R 1 . .
C C51 0.7777(2) 0.59763(13) 0.60521(18) 0.0203(5) Uani d . . . 1 . .
H H51A 0.770108 0.643212 0.585545 0.024 Uiso calc U . R 1 . .
H H51B 0.696663 0.585817 0.617831 0.024 Uiso calc U . R 1 . .
C C52 0.9034(2) 0.52298(13) 0.74410(18) 0.0198(5) Uani d . . . 1 . .
H H52 0.886289 0.493155 0.684161 0.024 Uiso calc U . R 1 . .
C C53 0.7991(3) 0.50819(14) 0.7906(2) 0.0248(6) Uani d . . . 1 . .
H H53A 0.813561 0.536155 0.850485 0.037 Uiso calc U . R 1 . .
H H53B 0.80804 0.463663 0.813451 0.037 Uiso calc U . R 1 . .
H H53C 0.709038 0.515271 0.737562 0.037 Uiso calc U . R 1 . .
C C54 1.0428(3) 0.50809(13) 0.8245(2) 0.0231(6) Uani d . . . 1 . .
H H54A 1.055667 0.530547 0.890355 0.028 Uiso calc U . R 1 . .
H H54B 1.049541 0.461792 0.839081 0.028 Uiso calc U . R 1 . .
C C55 0.8979(2) 0.63861(13) 0.77855(19) 0.0191(5) Uani d . . . 1 . .
H H55A 0.954837 0.624172 0.849828 0.023 Uiso calc U . R 1 . .
H H55B 0.805763 0.644337 0.775743 0.023 Uiso calc U . R 1 . .
C C56 0.9494(2) 0.70170(13) 0.75804(18) 0.0172(5) Uani d . . . 1 . .
C C57 1.0840(2) 0.70937(13) 0.77287(18) 0.0193(5) Uani d . . . 1 . .
C C58 1.1353(2) 0.76894(13) 0.7663(2) 0.0211(5) Uani d . . . 1 . .
C C59 1.0493(2) 0.82131(13) 0.74164(18) 0.0202(5) Uani d . . . 1 . .
H H59 1.084388 0.86223 0.737533 0.024 Uiso calc U . R 1 . .
C C60 0.9137(2) 0.81560(13) 0.72287(18) 0.0190(5) Uani d . . . 1 . .
C C61 0.8663(2) 0.75525(13) 0.73166(18) 0.0182(5) Uani d . . . 1 . .
H H61 0.774176 0.750241 0.719288 0.022 Uiso calc U . R 1 . .
C C62 1.2812(3) 0.77618(15) 0.7841(2) 0.0313(7) Uani d . . . 1 . .
H H62A 1.336853 0.762739 0.855299 0.047 Uiso calc U . R 1 . .
H H62B 1.300028 0.820874 0.774535 0.047 Uiso calc U . R 1 . .
H H62C 1.30153 0.749646 0.733977 0.047 Uiso calc U . R 1 . .
C C63 0.8229(3) 0.87288(13) 0.6944(2) 0.0249(6) Uani d . . . 1 . .
H H63A 0.877069 0.911708 0.706185 0.037 Uiso calc U . R 1 . .
H H63B 0.769923 0.873898 0.737905 0.037 Uiso calc U . R 1 . .
H H63C 0.76277 0.870316 0.620697 0.037 Uiso calc U . R 1 . .
N N1 0.1474(2) 0.28517(11) 0.63953(15) 0.0192(4) Uani d . . . 1 . .
N N2 0.58339(19) 0.60383(10) 0.99341(15) 0.0159(4) Uani d . . . 1 . .
N N3 0.89678(19) 0.58873(10) 0.70266(15) 0.0175(4) Uani d . . . 1 . .
O O1 0.30492(17) 0.32333(9) 0.83709(13) 0.0223(4) Uani d . . . 1 . .
H H1 0.280178 0.32179 0.771859 0.033 Uiso calc U . R 1 . .
O O2 0.1268(2) 0.42730(10) 0.65703(17) 0.0363(5) Uani d . . . 1 . .
H H2 0.206679 0.415281 0.675609 0.054 Uiso calc U . R 1 . .
O O3 0.3605(2) 0.36848(9) 0.58315(15) 0.0283(4) Uani d . . . 1 . .
H H3 0.390367 0.393689 0.633922 0.042 Uiso calc U . R 1 . .
O O4 0.58642(17) 0.45003(9) 1.01017(15) 0.0241(4) Uani d . . . 1 . .
H H4A 0.539483 0.482073 1.009218 0.036 Uiso calc U . R 1 . .
O O5 0.36919(16) 0.52523(9) 0.97849(14) 0.0220(4) Uani d . . . 1 . .
H H5 0.309344 0.525689 0.917969 0.033 Uiso calc U . R 1 . .
O O6 0.50585(19) 0.54516(9) 0.81420(13) 0.0239(4) Uani d . . . 1 . .
H H6A 0.532004 0.550067 0.879098 0.036 Uiso calc U . R 1 . .
O O7 1.00675(18) 0.59556(11) 0.55114(14) 0.0285(4) Uani d . . . 1 . .
H H7 1.000799 0.605075 0.607977 0.043 Uiso calc U . R 1 . .
O O8 1.14724(17) 0.52637(10) 0.79097(14) 0.0249(4) Uani d . . . 1 . .
H H8 1.14581 0.502532 0.741941 0.037 Uiso calc U . R 1 . .
O O9 1.17353(17) 0.65964(9) 0.80129(15) 0.0244(4) Uani d . . . 1 . .
H H9 1.1332 0.625515 0.776675 0.037 Uiso calc U . R 1 . .
O O10 0.4117(2) 0.42653(10) 0.76558(16) 0.0323(5) Uani d . . D 1 . .
H H1O 0.432(4) 0.4064(18) 0.822(2) 0.049 Uiso d U . D 1 . .
H H2O 0.444(4) 0.4640(13) 0.781(3) 0.049 Uiso d U . 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 0.0033 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_
_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
C2 C1 C9 . . 119.3(2) ?
C6 C1 C2 . . 119.1(2) ?
C6 C1 C9 . . 121.6(2) ?
C1 C2 C3 . . 121.2(2) ?
O1 C2 C1 . . 120.4(2) ?
O1 C2 C3 . . 118.4(2) ?
C2 C3 C7 . . 119.6(2) ?
C4 C3 C2 . . 117.6(2) ?
C4 C3 C7 . . 122.8(2) ?
C3 C4 H4 . . 118.6 ?
C5 C4 C3 . . 122.7(2) ?
C5 C4 H4 . . 118.7 ?
C4 C5 C8 . . 122.0(2) ?
C6 C5 C4 . . 117.8(2) ?
C6 C5 C8 . . 120.2(2) ?
C1 C6 C5 . . 121.6(2) ?
C1 C6 H6 . . 119.2 ?
C5 C6 H6 . . 119.2 ?
C3 C7 H7A . . 109.5 ?
C3 C7 H7B . . 109.5 ?
C3 C7 H7C . . 109.5 ?
H7A C7 H7B . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C5 C8 H8A . . 109.5 ?
C5 C8 H8B . . 109.5 ?
C5 C8 H8C . . 109.5 ?
H8A C8 H8B . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C1 C9 H9A . . 109.2 ?
C1 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
N1 C9 C1 . . 111.9(2) ?
N1 C9 H9A . . 109.2 ?
N1 C9 H9B . . 109.2 ?
C11 C10 H10 . . 106.8 ?
C12 C10 H10 . . 106.8 ?
C12 C10 C11 . . 110.3(2) ?
N1 C10 H10 . . 106.8 ?
N1 C10 C11 . . 114.1(2) ?
N1 C10 C12 . . 111.5(2) ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11B . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C10 C12 H12A . . 109.0 ?
C10 C12 H12B . . 109.0 ?
H12A C12 H12B . . 107.8 ?
O2 C12 C10 . . 113.0(2) ?
O2 C12 H12A . . 109.0 ?
O2 C12 H12B . . 109.0 ?
H13A C13 H13B . . 108.0 ?
C14 C13 H13A . . 109.4 ?
C14 C13 H13B . . 109.4 ?
N1 C13 H13A . . 109.4 ?
N1 C13 H13B . . 109.4 ?
N1 C13 C14 . . 111.4(2) ?
C15 C14 C13 . . 118.7(2) ?
C19 C14 C13 . . 122.9(2) ?
C19 C14 C15 . . 118.4(2) ?
C16 C15 C14 . . 121.2(3) ?
O3 C15 C14 . . 118.4(2) ?
O3 C15 C16 . . 120.3(2) ?
C15 C16 C20 . . 120.1(3) ?
C17 C16 C15 . . 118.0(3) ?
C17 C16 C20 . . 121.8(3) ?
C16 C17 H17 . . 118.8 ?
C16 C17 C18 . . 122.3(2) ?
C18 C17 H17 . . 118.8 ?
C17 C18 C19 . . 117.9(3) ?
C17 C18 C21 . . 120.2(3) ?
C19 C18 C21 . . 121.8(3) ?
C14 C19 C18 . . 122.0(3) ?
C14 C19 H19 . . 119.0 ?
C18 C19 H19 . . 119.0 ?
C16 C20 H20A . . 109.5 ?
C16 C20 H20B . . 109.5 ?
C16 C20 H20C . . 109.5 ?
H20A C20 H20B . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C18 C21 H21A . . 109.5 ?
C18 C21 H21B . . 109.5 ?
C18 C21 H21C . . 109.5 ?
H21A C21 H21B . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C23 C22 C27 . . 119.1(2) ?
C23 C22 C30 . . 121.2(2) ?
C27 C22 C30 . . 119.7(2) ?
C22 C23 C24 . . 120.5(2) ?
O4 C23 C22 . . 124.0(2) ?
O4 C23 C24 . . 115.5(2) ?
C23 C24 C28 . . 120.0(2) ?
C25 C24 C23 . . 118.3(2) ?
C25 C24 C28 . . 121.7(2) ?
C24 C25 H25 . . 118.7 ?
C26 C25 C24 . . 122.6(2) ?
C26 C25 H25 . . 118.7 ?
C25 C26 C27 . . 117.8(2) ?
C25 C26 C29 . . 121.9(2) ?
C27 C26 C29 . . 120.3(2) ?
C22 C27 H27 . . 119.1 ?
C26 C27 C22 . . 121.7(2) ?
C26 C27 H27 . . 119.1 ?
C24 C28 H28A . . 109.5 ?
C24 C28 H28B . . 109.5 ?
C24 C28 H28C . . 109.5 ?
H28A C28 H28B . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C26 C29 H29A . . 109.5 ?
C26 C29 H29B . . 109.5 ?
C26 C29 H29C . . 109.5 ?
H29A C29 H29B . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
C22 C30 H30A . . 109.4 ?
C22 C30 H30B . . 109.4 ?
H30A C30 H30B . . 108.0 ?
N2 C30 C22 . . 111.06(19) ?
N2 C30 H30A . . 109.4 ?
N2 C30 H30B . . 109.4 ?
C32 C31 H31 . . 107.2 ?
C32 C31 C33 . . 109.2(2) ?
C33 C31 H31 . . 107.2 ?
N2 C31 H31 . . 107.2 ?
N2 C31 C32 . . 115.7(2) ?
N2 C31 C33 . . 110.0(2) ?
C31 C32 H32A . . 109.5 ?
C31 C32 H32B . . 109.5 ?
C31 C32 H32C . . 109.5 ?
H32A C32 H32B . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
C31 C33 H33A . . 108.7 ?
C31 C33 H33B . . 108.7 ?
H33A C33 H33B . . 107.6 ?
O5 C33 C31 . . 114.2(2) ?
O5 C33 H33A . . 108.7 ?
O5 C33 H33B . . 108.7 ?
H34A C34 H34B . . 107.9 ?
C35 C34 H34A . . 109.2 ?
C35 C34 H34B . . 109.2 ?
N2 C34 H34A . . 109.2 ?
N2 C34 H34B . . 109.2 ?
N2 C34 C35 . . 111.98(19) ?
C36 C35 C34 . . 119.7(2) ?
C40 C35 C34 . . 121.6(2) ?
C40 C35 C36 . . 118.6(2) ?
C35 C36 C37 . . 121.3(2) ?
O6 C36 C35 . . 120.0(2) ?
O6 C36 C37 . . 118.7(2) ?
C36 C37 C41 . . 119.8(3) ?
C38 C37 C36 . . 117.7(2) ?
C38 C37 C41 . . 122.5(2) ?
C37 C38 H38 . . 118.6 ?
C37 C38 C39 . . 122.8(2) ?
C39 C38 H38 . . 118.6 ?
C38 C39 C40 . . 117.5(2) ?
C38 C39 C42 . . 121.2(2) ?
C40 C39 C42 . . 121.2(3) ?
C35 C40 C39 . . 122.0(2) ?
C35 C40 H40 . . 119.0 ?
C39 C40 H40 . . 119.0 ?
C37 C41 H41A . . 109.5 ?
C37 C41 H41B . . 109.5 ?
C37 C41 H41C . . 109.5 ?
H41A C41 H41B . . 109.5 ?
H41A C41 H41C . . 109.5 ?
H41B C41 H41C . . 109.5 ?
C39 C42 H42A . . 109.5 ?
C39 C42 H42B . . 109.5 ?
C39 C42 H42C . . 109.5 ?
H42A C42 H42B . . 109.5 ?
H42A C42 H42C . . 109.5 ?
H42B C42 H42C . . 109.5 ?
C44 C43 C51 . . 119.4(2) ?
C48 C43 C44 . . 119.0(2) ?
C48 C43 C51 . . 121.5(2) ?
C45 C44 C43 . . 120.8(3) ?
O7 C44 C43 . . 121.2(2) ?
O7 C44 C45 . . 118.0(2) ?
C44 C45 C49 . . 119.5(3) ?
C46 C45 C44 . . 118.2(3) ?
C46 C45 C49 . . 122.2(3) ?
C45 C46 H46 . . 118.7 ?
C47 C46 C45 . . 122.6(3) ?
C47 C46 H46 . . 118.7 ?
C46 C47 C48 . . 117.7(3) ?
C46 C47 C50 . . 121.2(3) ?
C48 C47 C50 . . 121.0(3) ?
C43 C48 C47 . . 121.7(3) ?
C43 C48 H48 . . 119.2 ?
C47 C48 H48 . . 119.2 ?
C45 C49 H49A . . 109.5 ?
C45 C49 H49B . . 109.5 ?
C45 C49 H49C . . 109.5 ?
H49A C49 H49B . . 109.5 ?
H49A C49 H49C . . 109.5 ?
H49B C49 H49C . . 109.5 ?
C47 C50 H50A . . 109.5 ?
C47 C50 H50B . . 109.5 ?
C47 C50 H50C . . 109.5 ?
H50A C50 H50B . . 109.5 ?
H50A C50 H50C . . 109.5 ?
H50B C50 H50C . . 109.5 ?
C43 C51 H51A . . 109.0 ?
C43 C51 H51B . . 109.0 ?
H51A C51 H51B . . 107.8 ?
N3 C51 C43 . . 112.9(2) ?
N3 C51 H51A . . 109.0 ?
N3 C51 H51B . . 109.0 ?
C53 C52 H52 . . 107.1 ?
C54 C52 H52 . . 107.1 ?
C54 C52 C53 . . 109.4(2) ?
N3 C52 H52 . . 107.1 ?
N3 C52 C53 . . 114.7(2) ?
N3 C52 C54 . . 111.1(2) ?
C52 C53 H53A . . 109.5 ?
C52 C53 H53B . . 109.5 ?
C52 C53 H53C . . 109.5 ?
H53A C53 H53B . . 109.5 ?
H53A C53 H53C . . 109.5 ?
H53B C53 H53C . . 109.5 ?
C52 C54 H54A . . 109.0 ?
C52 C54 H54B . . 109.0 ?
H54A C54 H54B . . 107.8 ?
O8 C54 C52 . . 113.0(2) ?
O8 C54 H54A . . 109.0 ?
O8 C54 H54B . . 109.0 ?
H55A C55 H55B . . 107.8 ?
C56 C55 H55A . . 109.0 ?
C56 C55 H55B . . 109.0 ?
N3 C55 H55A . . 109.0 ?
N3 C55 H55B . . 109.0 ?
N3 C55 C56 . . 112.9(2) ?
C57 C56 C55 . . 120.8(2) ?
C61 C56 C55 . . 120.7(2) ?
C61 C56 C57 . . 118.3(2) ?
C58 C57 C56 . . 121.0(2) ?
O9 C57 C56 . . 122.2(2) ?
O9 C57 C58 . . 116.7(2) ?
C57 C58 C59 . . 118.8(2) ?
C57 C58 C62 . . 120.0(2) ?
C59 C58 C62 . . 121.2(2) ?
C58 C59 H59 . . 118.9 ?
C60 C59 C58 . . 122.2(2) ?
C60 C59 H59 . . 118.9 ?
C59 C60 C63 . . 120.9(2) ?
C61 C60 C59 . . 117.4(2) ?
C61 C60 C63 . . 121.7(2) ?
C56 C61 H61 . . 118.8 ?
C60 C61 C56 . . 122.4(2) ?
C60 C61 H61 . . 118.8 ?
C58 C62 H62A . . 109.5 ?
C58 C62 H62B . . 109.5 ?
C58 C62 H62C . . 109.5 ?
H62A C62 H62B . . 109.5 ?
H62A C62 H62C . . 109.5 ?
H62B C62 H62C . . 109.5 ?
C60 C63 H63A . . 109.5 ?
C60 C63 H63B . . 109.5 ?
C60 C63 H63C . . 109.5 ?
H63A C63 H63B . . 109.5 ?
H63A C63 H63C . . 109.5 ?
H63B C63 H63C . . 109.5 ?
C9 N1 C10 . . 112.1(2) ?
C9 N1 C13 . . 109.4(2) ?
C13 N1 C10 . . 114.04(19) ?
C30 N2 C31 . . 115.20(18) ?
C30 N2 C34 . . 111.19(18) ?
C34 N2 C31 . . 111.81(19) ?
C51 N3 C52 . . 111.51(19) ?
C51 N3 C55 . . 109.09(19) ?
C55 N3 C52 . . 113.28(19) ?
C2 O1 H1 . . 109.5 ?
C12 O2 H2 . . 109.5 ?
C15 O3 H3 . . 109.5 ?
C23 O4 H4A . . 109.5 ?
C33 O5 H5 . . 109.5 ?
C36 O6 H6A . . 109.5 ?
C44 O7 H7 . . 109.5 ?
C54 O8 H8 . . 109.5 ?
C57 O9 H9 . . 109.5 ?
H1O O10 H2O . . 107.(4) ?
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
C1 C2 . 1.395(4) ?
C1 C6 . 1.390(3) ?
C1 C9 . 1.509(3) ?
C2 C3 . 1.400(3) ?
C2 O1 . 1.369(3) ?
C3 C4 . 1.396(4) ?
C3 C7 . 1.503(4) ?
C4 H4 . 0.95 ?
C4 C5 . 1.394(4) ?
C5 C6 . 1.392(3) ?
C5 C8 . 1.510(4) ?
C6 H6 . 0.95 ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C9 N1 . 1.476(3) ?
C10 H10 . 1.0 ?
C10 C11 . 1.530(4) ?
C10 C12 . 1.515(4) ?
C10 N1 . 1.491(3) ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C12 O2 . 1.434(4) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C13 C14 . 1.513(3) ?
C13 N1 . 1.486(3) ?
C14 C15 . 1.400(4) ?
C14 C19 . 1.386(4) ?
C15 C16 . 1.399(4) ?
C15 O3 . 1.378(3) ?
C16 C17 . 1.389(4) ?
C16 C20 . 1.509(4) ?
C17 H17 . 0.95 ?
C17 C18 . 1.390(4) ?
C18 C19 . 1.391(4) ?
C18 C21 . 1.505(4) ?
C19 H19 . 0.95 ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 C23 . 1.395(4) ?
C22 C27 . 1.396(3) ?
C22 C30 . 1.514(3) ?
C23 C24 . 1.406(4) ?
C23 O4 . 1.370(3) ?
C24 C25 . 1.394(4) ?
C24 C28 . 1.507(4) ?
C25 H25 . 0.95 ?
C25 C26 . 1.385(4) ?
C26 C27 . 1.394(4) ?
C26 C29 . 1.516(3) ?
C27 H27 . 0.95 ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
C29 H29A . 0.98 ?
C29 H29B . 0.98 ?
C29 H29C . 0.98 ?
C30 H30A . 0.99 ?
C30 H30B . 0.99 ?
C30 N2 . 1.477(3) ?
C31 H31 . 1.0 ?
C31 C32 . 1.519(4) ?
C31 C33 . 1.534(3) ?
C31 N2 . 1.487(3) ?
C32 H32A . 0.98 ?
C32 H32B . 0.98 ?
C32 H32C . 0.98 ?
C33 H33A . 0.99 ?
C33 H33B . 0.99 ?
C33 O5 . 1.423(3) ?
C34 H34A . 0.99 ?
C34 H34B . 0.99 ?
C34 C35 . 1.510(3) ?
C34 N2 . 1.481(3) ?
C35 C36 . 1.395(4) ?
C35 C40 . 1.384(4) ?
C36 C37 . 1.402(3) ?
C36 O6 . 1.369(3) ?
C37 C38 . 1.381(4) ?
C37 C41 . 1.509(4) ?
C38 H38 . 0.95 ?
C38 C39 . 1.391(4) ?
C39 C40 . 1.393(3) ?
C39 C42 . 1.506(4) ?
C40 H40 . 0.95 ?
C41 H41A . 0.98 ?
C41 H41B . 0.98 ?
C41 H41C . 0.98 ?
C42 H42A . 0.98 ?
C42 H42B . 0.98 ?
C42 H42C . 0.98 ?
C43 C44 . 1.398(4) ?
C43 C48 . 1.389(4) ?
C43 C51 . 1.510(4) ?
C44 C45 . 1.396(4) ?
C44 O7 . 1.365(3) ?
C45 C46 . 1.391(4) ?
C45 C49 . 1.504(4) ?
C46 H46 . 0.95 ?
C46 C47 . 1.388(5) ?
C47 C48 . 1.393(4) ?
C47 C50 . 1.518(4) ?
C48 H48 . 0.95 ?
C49 H49A . 0.98 ?
C49 H49B . 0.98 ?
C49 H49C . 0.98 ?
C50 H50A . 0.98 ?
C50 H50B . 0.98 ?
C50 H50C . 0.98 ?
C51 H51A . 0.99 ?
C51 H51B . 0.99 ?
C51 N3 . 1.476(3) ?
C52 H52 . 1.0 ?
C52 C53 . 1.531(3) ?
C52 C54 . 1.523(3) ?
C52 N3 . 1.487(3) ?
C53 H53A . 0.98 ?
C53 H53B . 0.98 ?
C53 H53C . 0.98 ?
C54 H54A . 0.99 ?
C54 H54B . 0.99 ?
C54 O8 . 1.430(3) ?
C55 H55A . 0.99 ?
C55 H55B . 0.99 ?
C55 C56 . 1.506(4) ?
C55 N3 . 1.482(3) ?
C56 C57 . 1.400(3) ?
C56 C61 . 1.397(4) ?
C57 C58 . 1.386(4) ?
C57 O9 . 1.374(3) ?
C58 C59 . 1.395(4) ?
C58 C62 . 1.508(3) ?
C59 H59 . 0.95 ?
C59 C60 . 1.392(3) ?
C60 C61 . 1.390(4) ?
C60 C63 . 1.506(4) ?
C61 H61 . 0.95 ?
C62 H62A . 0.98 ?
C62 H62B . 0.98 ?
C62 H62C . 0.98 ?
C63 H63A . 0.98 ?
C63 H63B . 0.98 ?
C63 H63C . 0.98 ?
O1 H1 . 0.84 ?
O2 H2 . 0.84 ?
O3 H3 . 0.84 ?
O4 H4A . 0.84 ?
O5 H5 . 0.84 ?
O6 H6A . 0.84 ?
O7 H7 . 0.84 ?
O8 H8 . 0.84 ?
O9 H9 . 0.84 ?
O10 H1O . 0.84(2) ?
O10 H2O . 0.86(2) ?
