#------------------------------------------------------------------------------
#$Date: 2022-06-06 04:47:09 +0300 (Mon, 06 Jun 2022) $
#$Revision: 275783 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/48/7244843.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_7244843
loop_
_publ_author_name
'Tao, Ji-Yu'
'Wang, Ying-Xue'
'Zhang, Qing-Hong'
'Ni, Kun'
'Zhu, Tong-Hao'
'Zhao, Kai'
_publ_section_title
;
 Transition-metal-free regioselective and stereoselective C(sp2)--C(sp3)
 coupling of enamides with ethers or alkanes via photoredox-catalyzed
 cross-dehydrogenative coupling reactions
;
_journal_issue                   10
_journal_name_full               'Green Chemistry'
_journal_page_first              4004
_journal_page_last               4011
_journal_paper_doi               10.1039/D2GC00472K
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C19 H25 N O4'
_chemical_formula_sum            'C19 H25 N O4'
_chemical_formula_weight         331.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-11 deposited with the CCDC.	2022-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.488(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.4311(8)
_cell_length_b                   10.9478(4)
_cell_length_c                   17.3130(7)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.922
_cell_measurement_theta_min      3.51
_cell_volume                     3650.6(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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      169.97
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            39169
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.003
_diffrn_reflns_theta_min         4.041
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.438
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1085 before and 0.0643 after correction. The Ratio of minimum to maximum transmission is 0.7658. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         6921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0506P)²+1.0687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1137
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5607
_reflns_number_total             6921
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2gc00472k2.cif
_cod_data_source_block           20190111sf
_cod_depositor_comments          'Adding full bibliography for 7244843.cif.'
_cod_database_code               7244843
_shelx_shelxl_version_number     2016/6
_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_max   0.978
_shelx_estimated_absorpt_t_min   0.957
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H7AA(0.5) H7AB(0.5) H7BC(0.5) H7BD(0.5) H10A(0.5) H10B(0.5)
 H10C(0.5) H10D(0.5) C9(0.5) H9A(0.5) H9B(0.5) C8(0.5) H8A(0.5) H8B(0.5)
 H7AC(0.5) H7AD(0.5) H7AE(0.5) H7AF(0.5) H10E(0.5) H10F(0.5) H10G(0.5)
 H10H(0.5) C8A(0.5) H8AA(0.5) H8AB(0.5) C9A(0.5) H9AA(0.5) H9AB(0.5)
3.a Ternary CH refined with riding coordinates:
 C6(H6), C6A(H6A)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7AA,H7AB), C7(H7BC,H7BD), C10(H10A,H10B), C10(H10C,H10D), C9(H9A,H9B),
 C8(H8A,H8B), C7A(H7AC,H7AD), C7A(H7AE,H7AF), C10A(H10E,H10F), C10A(H10G,H10H),
 C8A(H8AA,H8AB), C9A(H9AA,H9AB)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C5A(H5A),
 C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A), C16A(H16A)
3.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C3A(H3AA,H3AB,H3AC), C18A(H18D,H18E,H18F), C19A(H19D,H19E,H19F),
 C20A(H20D,H20E,H20F)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.86977(7) 0.44017(10) 0.38320(7) 0.0512(3) Uani 1 1 d . . . . .
O2 O 0.82400(6) 0.44057(10) 0.13851(7) 0.0427(3) Uani 1 1 d . . . . .
O3 O 0.91508(5) 0.31079(9) 0.16160(6) 0.0356(2) Uani 1 1 d . . . . .
O4 O 1.10556(6) 0.21144(12) 0.37263(7) 0.0537(3) Uani 1 1 d . . . . .
N1 N 0.89303(6) 0.38572(10) 0.26926(7) 0.0311(3) Uani 1 1 d . . . . .
C1 C 0.87251(8) 0.38476(12) 0.18334(9) 0.0317(3) Uani 1 1 d . . . . .
C2 C 0.86446(8) 0.46590(13) 0.31337(9) 0.0349(3) Uani 1 1 d . . . . .
C3 C 0.83162(9) 0.58183(14) 0.27382(10) 0.0419(4) Uani 1 1 d . . . . .
H3A H 0.785062 0.564554 0.235447 0.063 Uiso 1 1 calc GR . . . .
H3B H 0.860021 0.618277 0.244080 0.063 Uiso 1 1 calc GR . . . .
H3C H 0.828201 0.638850 0.315943 0.063 Uiso 1 1 calc GR . . . .
C4 C 0.93928(7) 0.28991(12) 0.31439(9) 0.0306(3) Uani 1 1 d . . . . .
C5 C 1.00281(8) 0.32194(13) 0.36078(9) 0.0359(3) Uani 1 1 d . . . . .
H5 H 1.014693 0.405606 0.359368 0.043 Uiso 1 1 calc R . . . .
C6 C 1.05760(8) 0.24075(15) 0.41491(10) 0.0402(4) Uani 1 1 d . . . . .
H6 H 1.035917 0.164080 0.426465 0.048 Uiso 1 1 calc R . . . .
C7 C 1.10114(9) 0.29987(19) 0.49533(11) 0.0527(5) Uani 1 1 d . . . . .
H7AA H 1.100775 0.389941 0.490123 0.063 Uiso 0.5 1 calc R . P A 1
H7AB H 1.083369 0.277534 0.540091 0.063 Uiso 0.5 1 calc R . P A 1
H7BC H 1.078249 0.373851 0.507110 0.063 Uiso 0.5 1 calc R . P B 2
H7BD H 1.110208 0.242078 0.541705 0.063 Uiso 0.5 1 calc R . P B 2
C10 C 1.17431(9) 0.2374(2) 0.42354(13) 0.0591(5) Uani 1 1 d . . . . .
H10A H 1.190850 0.314086 0.405946 0.071 Uiso 0.5 1 calc R . P C 1
H10B H 1.205919 0.170304 0.420730 0.071 Uiso 0.5 1 calc R . P C 1
H10C H 1.202545 0.266792 0.390625 0.071 Uiso 0.5 1 calc R . P D 2
H10D H 1.196612 0.163762 0.454344 0.071 Uiso 0.5 1 calc R . P D 2
C11 C 0.90864(7) 0.16572(13) 0.30351(9) 0.0313(3) Uani 1 1 d . . . . .
C12 C 0.94525(8) 0.06426(13) 0.29160(10) 0.0381(4) Uani 1 1 d . . . . .
H12 H 0.991221 0.073838 0.290766 0.046 Uiso 1 1 calc R . . . .
C13 C 0.91509(9) -0.05041(14) 0.28098(11) 0.0463(4) Uani 1 1 d . . . . .
H13 H 0.940415 -0.119189 0.272902 0.056 Uiso 1 1 calc R . . . .
C14 C 0.84836(9) -0.06520(15) 0.28207(12) 0.0516(4) Uani 1 1 d . . . . .
H14 H 0.827806 -0.144070 0.274811 0.062 Uiso 1 1 calc R . . . .
C15 C 0.81151(9) 0.03455(16) 0.29369(12) 0.0507(4) Uani 1 1 d . . . . .
H15 H 0.765669 0.024347 0.294856 0.061 Uiso 1 1 calc R . . . .
C16 C 0.84124(8) 0.14928(14) 0.30364(10) 0.0395(4) Uani 1 1 d . . . . .
H16 H 0.815287 0.217854 0.310668 0.047 Uiso 1 1 calc R . . . .
C17 C 0.90133(8) 0.27777(14) 0.07441(9) 0.0393(4) Uani 1 1 d . . . . .
C18 C 0.82947(9) 0.22380(17) 0.03780(12) 0.0541(5) Uani 1 1 d . . . . .
H18A H 0.823307 0.158215 0.073277 0.081 Uiso 1 1 calc GR . . . .
H18B H 0.823863 0.190685 -0.016628 0.081 Uiso 1 1 calc GR . . . .
H18C H 0.794648 0.287536 0.033002 0.081 Uiso 1 1 calc GR . . . .
C19 C 0.91239(11) 0.38969(18) 0.02899(11) 0.0562(5) Uani 1 1 d . . . . .
H19A H 0.876955 0.450959 0.027262 0.084 Uiso 1 1 calc GR . . . .
H19B H 0.908808 0.366917 -0.027013 0.084 Uiso 1 1 calc GR . . . .
H19C H 0.958564 0.423696 0.057315 0.084 Uiso 1 1 calc GR . . . .
C20 C 0.95649(10) 0.18229(19) 0.08182(12) 0.0583(5) Uani 1 1 d . . . . .
H20A H 0.953512 0.153928 0.027060 0.087 Uiso 1 1 calc GR . . . .
H20B H 0.949294 0.113163 0.114043 0.087 Uiso 1 1 calc GR . . . .
H20C H 1.002434 0.217860 0.109152 0.087 Uiso 1 1 calc GR . . . .
C9 C 1.17249(17) 0.2505(4) 0.5114(2) 0.0481(8) Uani 0.5 1 d . . P E 1
H9A H 1.178644 0.170607 0.539752 0.058 Uiso 0.5 1 calc R . P E 1
H9B H 1.208402 0.308081 0.544129 0.058 Uiso 0.5 1 calc R . P E 1
C8 C 1.1673(2) 0.3317(4) 0.4788(3) 0.0652(12) Uani 0.5 1 d . . P E 2
H8A H 1.163598 0.413308 0.453037 0.078 Uiso 0.5 1 calc R . P E 2
H8B H 1.207502 0.331354 0.530189 0.078 Uiso 0.5 1 calc R . P E 2
O1A O 0.61938(7) 0.58045(11) 0.48755(7) 0.0581(4) Uani 1 1 d . . . . .
O2A O 0.67510(6) 0.60727(10) 0.28654(7) 0.0456(3) Uani 1 1 d . . . . .
O3A O 0.57780(5) 0.72093(9) 0.23302(6) 0.0327(2) Uani 1 1 d . . . . .
O4A O 0.39598(5) 0.84487(11) 0.30000(7) 0.0486(3) Uani 1 1 d . . . . .
N1A N 0.60125(6) 0.64846(10) 0.35907(7) 0.0306(3) Uani 1 1 d . . . . .
C1A C 0.62342(7) 0.65424(12) 0.29026(9) 0.0317(3) Uani 1 1 d . . . . .
C2A C 0.62813(8) 0.56398(13) 0.42261(9) 0.0378(4) Uani 1 1 d . . . . .
C3A C 0.66416(10) 0.45233(15) 0.40727(11) 0.0478(4) Uani 1 1 d . . . . .
H3AA H 0.637708 0.417959 0.353658 0.072 Uiso 1 1 calc GR . . . .
H3AB H 0.667498 0.391705 0.450064 0.072 Uiso 1 1 calc GR . . . .
H3AC H 0.710889 0.474159 0.408025 0.072 Uiso 1 1 calc GR . . . .
C4A C 0.55679(7) 0.74637(12) 0.36903(8) 0.0301(3) Uani 1 1 d . . . . .
C5A C 0.49336(7) 0.71891(13) 0.36807(9) 0.0338(3) Uani 1 1 d . . . . .
H5A H 0.479629 0.635782 0.358867 0.041 Uiso 1 1 calc R . . . .
C6A C 0.44148(8) 0.80600(15) 0.38007(10) 0.0377(3) Uani 1 1 d . . . . .
H6A H 0.465967 0.878544 0.411843 0.045 Uiso 1 1 calc R . . . .
C7A C 0.39429(9) 0.74953(18) 0.42276(11) 0.0507(4) Uani 1 1 d . . . . .
H7AC H 0.414727 0.673505 0.451825 0.061 Uiso 0.5 1 calc R . P F 1
H7AD H 0.385992 0.807381 0.462464 0.061 Uiso 0.5 1 calc R . P F 1
H7AE H 0.394619 0.659213 0.420043 0.061 Uiso 0.5 1 calc R . P G 2
H7AF H 0.407895 0.775452 0.480767 0.061 Uiso 0.5 1 calc R . P G 2
C10A C 0.32620(9) 0.8222(2) 0.29277(13) 0.0623(5) Uani 1 1 d . . . . .
H10E H 0.299387 0.795270 0.236499 0.075 Uiso 0.5 1 calc R . P H 1
H10F H 0.304392 0.896947 0.305338 0.075 Uiso 0.5 1 calc R . P H 1
H10G H 0.308625 0.749768 0.257760 0.075 Uiso 0.5 1 calc R . P I 2
H10H H 0.296927 0.893286 0.267492 0.075 Uiso 0.5 1 calc R . P I 2
C11A C 0.58910(7) 0.86946(12) 0.37828(9) 0.0295(3) Uani 1 1 d . . . . .
C12A C 0.65762(8) 0.88470(14) 0.42851(10) 0.0370(3) Uani 1 1 d . . . . .
H12A H 0.682775 0.816734 0.457936 0.044 Uiso 1 1 calc R . . . .
C13A C 0.68975(8) 0.99773(15) 0.43626(11) 0.0461(4) Uani 1 1 d . . . . .
H13A H 0.736312 1.007370 0.471640 0.055 Uiso 1 1 calc R . . . .
C14A C 0.65383(9) 1.09636(14) 0.39233(11) 0.0442(4) Uani 1 1 d . . . . .
H14A H 0.676010 1.173544 0.396591 0.053 Uiso 1 1 calc R . . . .
C15A C 0.58574(9) 1.08266(14) 0.34228(10) 0.0404(4) Uani 1 1 d . . . . .
H15A H 0.561021 1.150668 0.312417 0.049 Uiso 1 1 calc R . . . .
C16A C 0.55338(8) 0.97033(13) 0.33545(9) 0.0345(3) Uani 1 1 d . . . . .
H16A H 0.506359 0.961848 0.301243 0.041 Uiso 1 1 calc R . . . .
C17A C 0.59404(8) 0.76636(14) 0.16036(9) 0.0360(3) Uani 1 1 d . . . . .
C18A C 0.66069(10) 0.83835(19) 0.18896(12) 0.0581(5) Uani 1 1 d . . . . .
H18D H 0.658222 0.899069 0.229487 0.087 Uiso 1 1 calc GR . . . .
H18E H 0.667507 0.879921 0.142088 0.087 Uiso 1 1 calc GR . . . .
H18F H 0.699682 0.782878 0.213894 0.087 Uiso 1 1 calc GR . . . .
C19A C 0.53278(9) 0.84920(16) 0.12040(10) 0.0489(4) Uani 1 1 d . . . . .
H19D H 0.489723 0.801697 0.106066 0.073 Uiso 1 1 calc GR . . . .
H19E H 0.537497 0.885105 0.070672 0.073 Uiso 1 1 calc GR . . . .
H19F H 0.531461 0.914468 0.158597 0.073 Uiso 1 1 calc GR . . . .
C20A C 0.59509(12) 0.66057(17) 0.10518(11) 0.0579(5) Uani 1 1 d . . . . .
H20D H 0.635332 0.608610 0.131982 0.087 Uiso 1 1 calc GR . . . .
H20E H 0.598209 0.691516 0.053412 0.087 Uiso 1 1 calc GR . . . .
H20F H 0.552402 0.612740 0.094251 0.087 Uiso 1 1 calc GR . . . .
C8A C 0.32811(19) 0.7233(4) 0.3535(3) 0.0513(9) Uani 0.5 1 d . . P J 1
H8AA H 0.329489 0.641420 0.329793 0.062 Uiso 0.5 1 calc R . P J 1
H8AB H 0.287308 0.728172 0.372065 0.062 Uiso 0.5 1 calc R . P J 1
C9A C 0.3238(2) 0.8015(5) 0.3724(3) 0.0630(11) Uani 0.5 1 d . . P J 2
H9AA H 0.286384 0.742847 0.370447 0.076 Uiso 0.5 1 calc R . P J 2
H9AB H 0.314860 0.878869 0.396716 0.076 Uiso 0.5 1 calc R . P J 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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
C1 O3 C17 121.03(11) . . ?
C10 O4 C6 109.90(13) . . ?
C1 N1 C2 123.13(12) . . ?
C1 N1 C4 118.36(11) . . ?
C2 N1 C4 118.05(12) . . ?
O2 C1 O3 127.04(13) . . ?
O2 C1 N1 124.79(13) . . ?
O3 C1 N1 108.16(12) . . ?
O1 C2 N1 118.70(13) . . ?
O1 C2 C3 122.24(13) . . ?
N1 C2 C3 119.00(13) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C11 114.99(12) . . ?
C5 C4 N1 117.68(12) . . ?
C5 C4 C11 127.32(13) . . ?
C4 C5 H5 116.5 . . ?
C4 C5 C6 126.97(14) . . ?
C6 C5 H5 116.5 . . ?
O4 C6 C5 107.97(13) . . ?
O4 C6 H6 109.7 . . ?
O4 C6 C7 105.67(12) . . ?
C5 C6 H6 109.7 . . ?
C5 C6 C7 114.10(14) . . ?
C7 C6 H6 109.7 . . ?
C6 C7 H7AA 110.8 . . ?
C6 C7 H7AB 110.8 . . ?
C6 C7 H7BC 111.3 . . ?
C6 C7 H7BD 111.3 . . ?
H7AA C7 H7AB 108.9 . . ?
H7BC C7 H7BD 109.2 . . ?
C9 C7 C6 104.63(18) . . ?
C9 C7 H7AA 110.8 . . ?
C9 C7 H7AB 110.8 . . ?
C8 C7 C6 102.2(2) . . ?
C8 C7 H7BC 111.3 . . ?
C8 C7 H7BD 111.3 . . ?
O4 C10 H10A 110.4 . . ?
O4 C10 H10B 110.4 . . ?
O4 C10 H10C 110.8 . . ?
O4 C10 H10D 110.8 . . ?
O4 C10 C9 106.71(18) . . ?
O4 C10 C8 104.9(2) . . ?
H10A C10 H10B 108.6 . . ?
H10C C10 H10D 108.8 . . ?
C9 C10 H10A 110.4 . . ?
C9 C10 H10B 110.4 . . ?
C8 C10 H10C 110.8 . . ?
C8 C10 H10D 110.8 . . ?
C12 C11 C4 121.70(13) . . ?
C16 C11 C4 119.69(13) . . ?
C16 C11 C12 118.60(13) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.41(14) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.21(15) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.96(15) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 119.98(16) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.83(15) . . ?
C15 C16 H16 119.6 . . ?
O3 C17 C18 110.44(12) . . ?
O3 C17 C19 108.70(13) . . ?
O3 C17 C20 101.50(13) . . ?
C18 C17 C19 113.02(15) . . ?
C20 C17 C18 110.97(15) . . ?
C20 C17 C19 111.59(15) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7 C9 C10 101.2(2) . . ?
C7 C9 H9A 111.5 . . ?
C7 C9 H9B 111.5 . . ?
C10 C9 H9A 111.5 . . ?
C10 C9 H9B 111.5 . . ?
H9A C9 H9B 109.4 . . ?
C7 C8 H8A 110.8 . . ?
C7 C8 H8B 110.8 . . ?
C10 C8 C7 104.7(3) . . ?
C10 C8 H8A 110.8 . . ?
C10 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C1A O3A C17A 120.96(11) . . ?
C10A O4A C6A 109.83(12) . . ?
C1A N1A C4A 117.20(11) . . ?
C2A N1A C1A 122.73(12) . . ?
C2A N1A C4A 119.39(11) . . ?
O2A C1A O3A 127.48(13) . . ?
O2A C1A N1A 124.38(14) . . ?
O3A C1A N1A 108.14(11) . . ?
O1A C2A N1A 119.38(13) . . ?
O1A C2A C3A 121.41(14) . . ?
N1A C2A C3A 119.15(13) . . ?
C2A C3A H3AA 109.5 . . ?
C2A C3A H3AB 109.5 . . ?
C2A C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
N1A C4A C11A 114.17(11) . . ?
C5A C4A N1A 118.62(13) . . ?
C5A C4A C11A 127.21(13) . . ?
C4A C5A H5A 116.9 . . ?
C4A C5A C6A 126.23(14) . . ?
C6A C5A H5A 116.9 . . ?
O4A C6A C5A 108.24(12) . . ?
O4A C6A H6A 109.6 . . ?
O4A C6A C7A 105.92(12) . . ?
C5A C6A H6A 109.6 . . ?
C5A C6A C7A 113.66(13) . . ?
C7A C6A H6A 109.6 . . ?
C6A C7A H7AC 111.0 . . ?
C6A C7A H7AD 111.0 . . ?
C6A C7A H7AE 111.5 . . ?
C6A C7A H7AF 111.5 . . ?
H7AC C7A H7AD 109.0 . . ?
H7AE C7A H7AF 109.3 . . ?
C8A C7A C6A 103.64(19) . . ?
C8A C7A H7AC 111.0 . . ?
C8A C7A H7AD 111.0 . . ?
C9A C7A C6A 101.6(2) . . ?
C9A C7A H7AE 111.5 . . ?
C9A C7A H7AF 111.5 . . ?
O4A C10A H10E 110.5 . . ?
O4A C10A H10F 110.5 . . ?
O4A C10A H10G 110.2 . . ?
O4A C10A H10H 110.2 . . ?
O4A C10A C8A 106.0(2) . . ?
O4A C10A C9A 107.7(2) . . ?
H10E C10A H10F 108.7 . . ?
H10G C10A H10H 108.5 . . ?
C8A C10A H10E 110.5 . . ?
C8A C10A H10F 110.5 . . ?
C9A C10A H10G 110.2 . . ?
C9A C10A H10H 110.2 . . ?
C12A C11A C4A 119.66(13) . . ?
C12A C11A C16A 118.52(13) . . ?
C16A C11A C4A 121.77(13) . . ?
C11A C12A H12A 119.6 . . ?
C13A C12A C11A 120.88(14) . . ?
C13A C12A H12A 119.6 . . ?
C12A C13A H13A 120.1 . . ?
C14A C13A C12A 119.79(15) . . ?
C14A C13A H13A 120.1 . . ?
C13A C14A H14A 120.0 . . ?
C15A C14A C13A 119.97(15) . . ?
C15A C14A H14A 120.0 . . ?
C14A C15A H15A 119.9 . . ?
C14A C15A C16A 120.24(14) . . ?
C16A C15A H15A 119.9 . . ?
C11A C16A H16A 119.7 . . ?
C15A C16A C11A 120.58(14) . . ?
C15A C16A H16A 119.7 . . ?
O3A C17A C18A 109.19(12) . . ?
O3A C17A C19A 101.71(12) . . ?
O3A C17A C20A 109.47(12) . . ?
C18A C17A C19A 110.83(14) . . ?
C20A C17A C18A 114.09(15) . . ?
C20A C17A C19A 110.83(15) . . ?
C17A C18A H18D 109.5 . . ?
C17A C18A H18E 109.5 . . ?
C17A C18A H18F 109.5 . . ?
H18D C18A H18E 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C17A C19A H19D 109.5 . . ?
C17A C19A H19E 109.5 . . ?
C17A C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C17A C20A H20D 109.5 . . ?
C17A C20A H20E 109.5 . . ?
C17A C20A H20F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C7A C8A H8AA 111.1 . . ?
C7A C8A H8AB 111.1 . . ?
C10A C8A C7A 103.1(2) . . ?
C10A C8A H8AA 111.1 . . ?
C10A C8A H8AB 111.1 . . ?
H8AA C8A H8AB 109.1 . . ?
C7A C9A H9AA 110.4 . . ?
C7A C9A H9AB 110.4 . . ?
C10A C9A C7A 106.5(3) . . ?
C10A C9A H9AA 110.4 . . ?
C10A C9A H9AB 110.4 . . ?
H9AA C9A H9AB 108.6 . . ?
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
O1 C2 1.2104(18) . ?
O2 C1 1.2020(17) . ?
O3 C1 1.3313(17) . ?
O3 C17 1.4850(18) . ?
O4 C6 1.4414(19) . ?
O4 C10 1.416(2) . ?
N1 C1 1.4045(19) . ?
N1 C2 1.4115(18) . ?
N1 C4 1.4530(18) . ?
C2 C3 1.491(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.326(2) . ?
C4 C11 1.482(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.490(2) . ?
C6 H6 1.0000 . ?
C6 C7 1.524(2) . ?
C7 H7AA 0.9900 . ?
C7 H7AB 0.9900 . ?
C7 H7BC 0.9900 . ?
C7 H7BD 0.9900 . ?
C7 C9 1.491(4) . ?
C7 C8 1.512(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 H10C 0.9900 . ?
C10 H10D 0.9900 . ?
C10 C9 1.540(4) . ?
C10 C8 1.447(5) . ?
C11 C12 1.392(2) . ?
C11 C16 1.390(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.379(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.512(2) . ?
C17 C19 1.513(2) . ?
C17 C20 1.511(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
O1A C2A 1.2094(18) . ?
O2A C1A 1.1954(17) . ?
O3A C1A 1.3294(17) . ?
O3A C17A 1.4895(17) . ?
O4A C6A 1.4516(19) . ?
O4A C10A 1.411(2) . ?
N1A C1A 1.4101(18) . ?
N1A C2A 1.4015(19) . ?
N1A C4A 1.4520(17) . ?
C2A C3A 1.496(2) . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A H3AC 0.9800 . ?
C4A C5A 1.325(2) . ?
C4A C11A 1.4856(19) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.491(2) . ?
C6A H6A 1.0000 . ?
C6A C7A 1.528(2) . ?
C7A H7AC 0.9900 . ?
C7A H7AD 0.9900 . ?
C7A H7AE 0.9900 . ?
C7A H7AF 0.9900 . ?
C7A C8A 1.506(4) . ?
C7A C9A 1.523(5) . ?
C10A H10E 0.9900 . ?
C10A H10F 0.9900 . ?
C10A H10G 0.9900 . ?
C10A H10H 0.9900 . ?
C10A C8A 1.501(4) . ?
C10A C9A 1.414(5) . ?
C11A C12A 1.390(2) . ?
C11A C16A 1.393(2) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.386(2) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.382(2) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.380(2) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.383(2) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.507(2) . ?
C17A C19A 1.513(2) . ?
C17A C20A 1.506(2) . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
