#------------------------------------------------------------------------------
#$Date: 2026-03-04 00:31:19 +0100 (Wed 04 de Mar de 2026) $
#$Revision: 304701 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/55/7135521.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_7135521
loop_
_publ_author_name
'Alharthi, Asma A.'
'Kariuki, Benson M.'
'Morrill, Louis C.'
'Browne, Duncan L.'
_publ_section_title
;
 Mechanochemical one-pot Barbier/Simmons-Smith reaction via
 sequential zinc activation.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1864
_journal_page_last               1868
_journal_paper_doi               10.1039/d5cc05732a
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C21 H23 N O5'
_chemical_formula_sum            'C21 H23 N O5'
_chemical_formula_weight         369.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-04-10 deposited with the CCDC.	2025-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.294(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   37.342(3)
_cell_length_b                   6.4577(6)
_cell_length_c                   15.8102(9)
_cell_measurement_reflns_used    807
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      67.6110
_cell_measurement_theta_min      5.6270
_cell_volume                     3796.3(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.120a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.120a (release 16-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.120a (Rigaku OD, 2024)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.5082
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5495
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.836
_diffrn_reflns_theta_min         4.757
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.120a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       needle
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5495
_refine_ls_number_restraints     723
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1524
_refine_ls_R_factor_gt           0.0817
_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)+(0.0981P)²+0.7241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2045
_refine_ls_wR_factor_ref         0.2358
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2568
_reflns_number_total             5495
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc05732a2.cif
_cod_data_source_block           lm2503
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7135521
_shelx_shelxl_version_number     2019/3
_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   0.694
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.28770(6) 0.0004(6) 0.50187(15) 0.0451(12) Uani 1 1 d G . . . .
C2 C 0.25095(7) -0.0048(5) 0.47789(12) 0.0433(11) Uani 1 1 d G . . . .
H2 H 0.242438 -0.015601 0.419545 0.052 Uiso 1 1 calc R U . . .
C3 C 0.22665(5) 0.0057(5) 0.53926(16) 0.0390(10) Uani 1 1 d G . . . .
H3 H 0.201531 0.002134 0.522869 0.047 Uiso 1 1 calc R U . . .
C4 C 0.23910(7) 0.0215(6) 0.62462(14) 0.0436(12) Uani 1 1 d G . . . .
C5 C 0.27584(7) 0.0267(6) 0.64861(12) 0.0566(15) Uani 1 1 d G . . . .
H5 H 0.284353 0.037490 0.706951 0.068 Uiso 1 1 calc R U . . .
C6 C 0.30014(5) 0.0162(6) 0.58723(17) 0.0537(14) Uani 1 1 d G . . . .
H6 H 0.325261 0.019755 0.603628 0.064 Uiso 1 1 calc R U . . .
C7 C 0.21526(14) 0.0250(9) 0.6938(3) 0.0498(13) Uani 1 1 d . . . . .
C8 C 0.1541(2) -0.0104(12) 0.7203(5) 0.0531(16) Uani 0.753(5) 1 d DG U P A 1
C9 C 0.1380(2) -0.2007(11) 0.7327(6) 0.057(2) Uani 0.753(5) 1 d DG U P A 1
H9 H 0.145847 -0.320596 0.704887 0.069 Uiso 0.753(5) 1 calc R U P A 1
C10 C 0.1105(2) -0.2155(12) 0.7859(5) 0.059(2) Uani 0.753(5) 1 d DG U P A 1
H10 H 0.099522 -0.345602 0.794448 0.071 Uiso 0.753(5) 1 calc R U P A 1
C11 C 0.09909(16) -0.0401(15) 0.8267(4) 0.0520(16) Uani 0.753(5) 1 d DG U P A 1
C12 C 0.11519(17) 0.1503(13) 0.8143(4) 0.055(2) Uani 0.753(5) 1 d DG U P A 1
H12 H 0.107376 0.270185 0.842134 0.066 Uiso 0.753(5) 1 calc R U P A 1
C13 C 0.1427(2) 0.1651(11) 0.7611(4) 0.055(2) Uani 0.753(5) 1 d DG U P A 1
H13 H 0.153701 0.295196 0.752573 0.065 Uiso 0.753(5) 1 calc R U P A 1
C14 C 0.06869(18) -0.058(2) 0.8855(5) 0.0573(18) Uani 0.753(5) 1 d D U P A 1
H14 H 0.064433 0.085844 0.905431 0.069 Uiso 0.753(5) 1 calc R U P A 1
C15 C 0.03442(18) -0.1210(15) 0.8347(5) 0.071(2) Uani 0.753(5) 1 d D U P A 1
H15A H 0.034496 -0.270938 0.825223 0.106 Uiso 0.753(5) 1 calc R U P A 1
H15B H 0.032578 -0.049234 0.779803 0.106 Uiso 0.753(5) 1 calc R U P A 1
H15C H 0.013846 -0.083551 0.865768 0.106 Uiso 0.753(5) 1 calc R U P A 1
C16 C 0.07992(19) -0.1810(13) 0.9650(4) 0.0601(17) Uani 0.753(5) 1 d D U P A 1
C17 C 0.1147(2) -0.0940(18) 1.0110(6) 0.074(3) Uani 0.753(5) 1 d D U P A 1
H17A H 0.122426 -0.182380 1.059736 0.111 Uiso 0.753(5) 1 calc R U P A 1
H17B H 0.110421 0.046746 1.030849 0.111 Uiso 0.753(5) 1 calc R U P A 1
H17C H 0.133596 -0.091058 0.971813 0.111 Uiso 0.753(5) 1 calc R U P A 1
C18 C 0.0497(2) -0.1829(16) 1.0248(5) 0.075(2) Uani 0.753(5) 1 d D U P A 1
H18A H 0.044716 -0.038112 1.040667 0.090 Uiso 0.753(5) 1 calc R U P A 1
H18B H 0.027658 -0.237873 0.993114 0.090 Uiso 0.753(5) 1 calc R U P A 1
C19 C 0.0570(3) -0.3059(17) 1.1043(6) 0.091(2) Uani 0.753(5) 1 d D U P A 1
H19 H 0.079057 -0.265735 1.141290 0.109 Uiso 0.753(5) 1 calc R U P A 1
C20 C 0.0278(3) -0.396(2) 1.1487(7) 0.105(3) Uani 0.753(5) 1 d D U P A 1
H20A H 0.002759 -0.365539 1.125661 0.126 Uiso 0.753(5) 1 calc R U P A 1
H20B H 0.031399 -0.405151 1.211372 0.126 Uiso 0.753(5) 1 calc R U P A 1
C21 C 0.0491(3) -0.5361(17) 1.0992(8) 0.102(3) Uani 0.753(5) 1 d D U P A 1
H21A H 0.037516 -0.591537 1.045014 0.122 Uiso 0.753(5) 1 calc R U P A 1
H21B H 0.066216 -0.631233 1.130907 0.122 Uiso 0.753(5) 1 calc R U P A 1
O4 O 0.18028(9) -0.0029(6) 0.6624(2) 0.0583(10) Uani 0.753(5) 1 d D U P A 1
O5 O 0.08569(16) -0.3898(9) 0.9368(3) 0.0698(16) Uani 0.753(5) 1 d D U P A 1
H5A H 0.086179 -0.470795 0.978515 0.105 Uiso 0.753(5) 1 calc R U P A 1
C8A C 0.1547(8) -0.016(4) 0.7227(19) 0.055(3) Uani 0.247(5) 1 d D U P A 2
C9A C 0.1335(8) -0.192(4) 0.722(2) 0.056(3) Uani 0.247(5) 1 d D U P A 2
H9A H 0.137502 -0.304672 0.685297 0.067 Uiso 0.247(5) 1 calc R U P A 2
C10A C 0.1062(8) -0.197(5) 0.7758(19) 0.055(3) Uani 0.247(5) 1 d D U P A 2
H10A H 0.091404 -0.317155 0.775914 0.066 Uiso 0.247(5) 1 calc R U P A 2
C11A C 0.0996(6) -0.034(5) 0.8301(14) 0.054(3) Uani 0.247(5) 1 d D U P A 2
C12A C 0.1224(7) 0.136(5) 0.8306(16) 0.053(3) Uani 0.247(5) 1 d D U P A 2
H12A H 0.119693 0.244828 0.869896 0.064 Uiso 0.247(5) 1 calc R U P A 2
C13A C 0.1491(7) 0.151(4) 0.7750(17) 0.055(3) Uani 0.247(5) 1 d D U P A 2
H13A H 0.163206 0.272767 0.773079 0.066 Uiso 0.247(5) 1 calc R U P A 2
C14A C 0.0705(4) -0.054(6) 0.8923(9) 0.059(3) Uani 0.247(5) 1 d D U P A 2
H14A H 0.061221 -0.198431 0.885061 0.070 Uiso 0.247(5) 1 calc R U P A 2
C15A C 0.0391(6) 0.083(5) 0.8623(16) 0.085(6) Uani 0.247(5) 1 d D U P A 2
H15D H 0.021050 0.077817 0.903320 0.127 Uiso 0.247(5) 1 calc R U P A 2
H15E H 0.028499 0.034316 0.806846 0.127 Uiso 0.247(5) 1 calc R U P A 2
H15F H 0.047528 0.225895 0.857034 0.127 Uiso 0.247(5) 1 calc R U P A 2
C16A C 0.0843(4) -0.037(3) 0.9849(10) 0.066(3) Uani 0.247(5) 1 d D U P A 2
C17A C 0.1167(6) -0.181(4) 1.0059(19) 0.069(7) Uani 0.247(5) 1 d D U P A 2
H17D H 0.134920 -0.155023 0.966329 0.104 Uiso 0.247(5) 1 calc R U P A 2
H17E H 0.108807 -0.325954 1.000638 0.104 Uiso 0.247(5) 1 calc R U P A 2
H17F H 0.127099 -0.155441 1.064161 0.104 Uiso 0.247(5) 1 calc R U P A 2
C18A C 0.0554(6) -0.080(3) 1.0455(14) 0.076(3) Uani 0.247(5) 1 d D U P A 2
H18C H 0.065792 -0.045883 1.103722 0.091 Uiso 0.247(5) 1 calc R U P A 2
H18D H 0.035332 0.017379 1.031183 0.091 Uiso 0.247(5) 1 calc R U P A 2
C19A C 0.0399(7) -0.292(4) 1.0478(15) 0.093(3) Uani 0.247(5) 1 d D U P A 2
H19A H 0.030534 -0.349849 0.991433 0.112 Uiso 0.247(5) 1 calc R U P A 2
C20A C 0.0221(8) -0.368(6) 1.121(2) 0.101(4) Uani 0.247(5) 1 d D U P A 2
H20C H 0.001694 -0.465524 1.109349 0.121 Uiso 0.247(5) 1 calc R U P A 2
H20D H 0.019561 -0.271006 1.168383 0.121 Uiso 0.247(5) 1 calc R U P A 2
C21A C 0.0588(8) -0.446(5) 1.109(2) 0.098(4) Uani 0.247(5) 1 d D U P A 2
H21C H 0.061101 -0.590869 1.089386 0.118 Uiso 0.247(5) 1 calc R U P A 2
H21D H 0.079005 -0.395961 1.148539 0.118 Uiso 0.247(5) 1 calc R U P A 2
O4A O 0.18028(9) -0.0029(6) 0.6624(2) 0.0583(10) Uani 0.247(5) 1 d D U P A 2
O5A O 0.0960(5) 0.175(3) 0.9977(12) 0.093(5) Uani 0.247(5) 1 d D U P A 2
H5A1 H 0.086024 0.249362 0.958917 0.140 Uiso 0.247(5) 1 calc R U P A 2
N1 N 0.31275(12) -0.0174(7) 0.4380(3) 0.0505(11) Uani 1 1 d . . . . .
O1 O 0.30255(10) 0.0238(7) 0.3646(2) 0.0656(11) Uani 1 1 d . . . . .
O2 O 0.34350(11) -0.0767(8) 0.4613(3) 0.0762(14) Uani 1 1 d . . . . .
O3 O 0.22439(10) 0.0466(8) 0.7669(2) 0.0741(14) Uani 1 1 d . . . . .
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
_geom_angle_publ_flag
C2 C1 C6 120.0 . . ?
C2 C1 N1 119.6(3) . . ?
C6 C1 N1 120.3(3) . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 C7 123.5(3) . . ?
C5 C4 C7 116.5(3) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O3 C7 O4A 123.4(5) . . ?
O3 C7 O4 123.4(5) . . ?
O3 C7 C4 126.0(5) . . ?
O4A C7 C4 110.5(4) . . ?
O4 C7 C4 110.5(4) . . ?
C9 C8 C13 120.0 . . ?
C9 C8 O4 117.4(4) . . ?
C13 C8 O4 122.5(4) . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 C14 119.6(5) . . ?
C12 C11 C14 120.4(5) . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 120.0 . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C15 C14 C16 117.5(9) . . ?
C15 C14 C11 109.7(6) . . ?
C16 C14 C11 112.3(6) . . ?
C15 C14 H14 105.5 . . ?
C16 C14 H14 105.5 . . ?
C11 C14 H14 105.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O5 C16 C14 105.8(7) . . ?
O5 C16 C17 110.1(7) . . ?
C14 C16 C17 111.1(8) . . ?
O5 C16 C18 108.7(6) . . ?
C14 C16 C18 110.6(6) . . ?
C17 C16 C18 110.4(7) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C16 115.9(8) . . ?
C19 C18 H18A 108.3 . . ?
C16 C18 H18A 108.3 . . ?
C19 C18 H18B 108.3 . . ?
C16 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
C20 C19 C18 121.9(9) . . ?
C20 C19 C21 59.2(7) . . ?
C18 C19 C21 117.3(9) . . ?
C20 C19 H19 115.5 . . ?
C18 C19 H19 115.5 . . ?
C21 C19 H19 115.5 . . ?
C19 C20 C21 62.0(6) . . ?
C19 C20 H20A 117.6 . . ?
C21 C20 H20A 117.6 . . ?
C19 C20 H20B 117.6 . . ?
C21 C20 H20B 117.6 . . ?
H20A C20 H20B 114.7 . . ?
C20 C21 C19 58.8(7) . . ?
C20 C21 H21A 117.9 . . ?
C19 C21 H21A 117.9 . . ?
C20 C21 H21B 117.9 . . ?
C19 C21 H21B 117.9 . . ?
H21A C21 H21B 115.0 . . ?
C7 O4 C8 117.9(5) . . ?
C16 O5 H5A 109.5 . . ?
C13A C8A C9A 121.7(11) . . ?
C13A C8A O4A 120.6(13) . . ?
C9A C8A O4A 117.5(13) . . ?
C8A C9A C10A 117.8(12) . . ?
C8A C9A H9A 121.1 . . ?
C10A C9A H9A 121.1 . . ?
C9A C10A C11A 122.5(13) . . ?
C9A C10A H10A 118.8 . . ?
C11A C10A H10A 118.8 . . ?
C12A C11A C10A 117.3(11) . . ?
C12A C11A C14A 122.2(13) . . ?
C10A C11A C14A 120.2(13) . . ?
C11A C12A C13A 121.7(13) . . ?
C11A C12A H12A 119.1 . . ?
C13A C12A H12A 119.1 . . ?
C8A C13A C12A 118.8(13) . . ?
C8A C13A H13A 120.6 . . ?
C12A C13A H13A 120.6 . . ?
C15A C14A C16A 116.8(18) . . ?
C15A C14A C11A 108.8(14) . . ?
C16A C14A C11A 114.5(13) . . ?
C15A C14A H14A 105.2 . . ?
C16A C14A H14A 105.2 . . ?
C11A C14A H14A 105.2 . . ?
C14A C15A H15D 109.5 . . ?
C14A C15A H15E 109.5 . . ?
H15D C15A H15E 109.5 . . ?
C14A C15A H15F 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
O5A C16A C14A 106.0(15) . . ?
O5A C16A C18A 107.8(12) . . ?
C14A C16A C18A 113.2(13) . . ?
O5A C16A C17A 108.8(14) . . ?
C14A C16A C17A 111.0(14) . . ?
C18A C16A C17A 109.8(13) . . ?
C16A C17A H17D 109.5 . . ?
C16A C17A H17E 109.5 . . ?
H17D C17A H17E 109.5 . . ?
C16A C17A H17F 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
C19A C18A C16A 118.7(15) . . ?
C19A C18A H18C 107.6 . . ?
C16A C18A H18C 107.6 . . ?
C19A C18A H18D 107.6 . . ?
C16A C18A H18D 107.6 . . ?
H18C C18A H18D 107.1 . . ?
C20A C19A C18A 122(2) . . ?
C20A C19A C21A 59.7(9) . . ?
C18A C19A C21A 117.5(19) . . ?
C20A C19A H19A 115.3 . . ?
C18A C19A H19A 115.3 . . ?
C21A C19A H19A 115.3 . . ?
C19A C20A C21A 61.7(9) . . ?
C19A C20A H20C 117.6 . . ?
C21A C20A H20C 117.6 . . ?
C19A C20A H20D 117.6 . . ?
C21A C20A H20D 117.6 . . ?
H20C C20A H20D 114.7 . . ?
C20A C21A C19A 58.7(9) . . ?
C20A C21A H21C 117.9 . . ?
C19A C21A H21C 117.9 . . ?
C20A C21A H21D 117.9 . . ?
C19A C21A H21D 117.9 . . ?
H21C C21A H21D 115.1 . . ?
C7 O4A C8A 116.5(16) . . ?
C16A O5A H5A1 109.5 . . ?
O1 N1 O2 123.6(4) . . ?
O1 N1 C1 118.9(4) . . ?
O2 N1 C1 117.5(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 N1 1.443(5) . ?
C2 C3 1.3900 . ?
C2 H2 0.9500 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 C7 1.473(5) . ?
C5 C6 1.3900 . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O3 1.182(6) . ?
C7 O4A 1.366(6) . ?
C7 O4 1.366(6) . ?
C8 C9 1.3900 . ?
C8 C13 1.3900 . ?
C8 O4 1.399(5) . ?
C9 C10 1.3900 . ?
C9 H9 0.9500 . ?
C10 C11 1.3900 . ?
C10 H10 0.9500 . ?
C11 C12 1.3900 . ?
C11 C14 1.537(6) . ?
C12 C13 1.3900 . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.503(11) . ?
C14 C16 1.511(10) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 O5 1.443(9) . ?
C16 C17 1.537(11) . ?
C16 C18 1.538(9) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.490(12) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.470(13) . ?
C19 C21 1.516(13) . ?
C19 H19 1.0000 . ?
C20 C21 1.476(14) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
O5 H5A 0.8400 . ?
C8A C13A 1.383(11) . ?
C8A C9A 1.385(11) . ?
C8A O4A 1.411(10) . ?
C9A C10A 1.393(11) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.397(11) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.386(11) . ?
C11A C14A 1.539(11) . ?
C12A C13A 1.392(11) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?
C14A C15A 1.506(16) . ?
C14A C16A 1.510(14) . ?
C14A H14A 1.0000 . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?
C16A O5A 1.443(13) . ?
C16A C18A 1.534(13) . ?
C16A C17A 1.540(14) . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9800 . ?
C17A H17F 0.9800 . ?
C18A C19A 1.486(16) . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C19A C20A 1.472(17) . ?
C19A C21A 1.517(17) . ?
C19A H19A 1.0000 . ?
C20A C21A 1.487(17) . ?
C20A H20C 0.9900 . ?
C20A H20D 0.9900 . ?
C21A H21C 0.9900 . ?
C21A H21D 0.9900 . ?
O5A H5A1 0.8400 . ?
N1 O1 1.217(5) . ?
N1 O2 1.234(5) . ?
