#------------------------------------------------------------------------------
#$Date: 2021-04-05 17:29:25 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263712 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/03/1560370.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_1560370
loop_
_publ_author_name
'Yang, Jinghui'
'Xia, Yan'
_publ_section_title
;
 Mechanochemical generation of acid-degradable poly(enol ether)s
;
_journal_issue                   12
_journal_name_full               'Chemical Science'
_journal_page_first              4389
_journal_page_last               4394
_journal_paper_doi               10.1039/D1SC00001B
_journal_volume                  12
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H20 N2 O9'
_chemical_formula_sum            'C22 H20 N2 O9'
_chemical_formula_weight         456.40
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-12 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.7080(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.8601(4)
_cell_length_b                   20.5081(11)
_cell_length_c                   7.3450(4)
_cell_measurement_reflns_used    9658
_cell_measurement_temperature    100
_cell_measurement_theta_max      80.022
_cell_measurement_theta_min      4.311
_cell_volume                     1032.20(10)
_computing_cell_refinement       'SAINT  V8.40A (2019)'
_computing_data_reduction        'SAINT  V8.40A (2019)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon II'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_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  0.0230
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            56702
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.238
_diffrn_reflns_theta_min         4.312
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.983
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1312 before and 0.0429 after correction. 
The Ratio of minimum to maximum transmission is 0.8237. 
The λ/2 correction factor is Not present.'
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 2128 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       0.0047(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4448
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0556P)²+0.1350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0776
_reflns_Friedel_coverage         0.929
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                4443
_reflns_number_total             4448
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc00001b2.cif
_cod_data_source_block           cu_jy_05_148_0m_a
_cod_depositor_comments          'Adding full bibliography for 1560370.cif.'
_cod_database_code               1560370
_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   0.883
_shelx_estimated_absorpt_t_min   0.538
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
O8 O 0.97032(17) 0.52214(6) 0.91249(16) 0.0243(2) Uani 1 1 d . . . . .
O5 O 0.99836(18) 0.57803(6) 0.51529(18) 0.0280(3) Uani 1 1 d . . . . .
O6 O 0.74051(17) 0.62285(6) 0.64886(16) 0.0253(3) Uani 1 1 d . . . . .
O7 O 1.24111(18) 0.46735(6) 0.83964(18) 0.0297(3) Uani 1 1 d . . . . .
O9 O 1.26535(18) 0.69136(6) 1.13787(17) 0.0292(3) Uani 1 1 d . . . . .
O3 O 0.12449(18) 0.40185(7) 0.21907(19) 0.0334(3) Uani 1 1 d . . . . .
O2 O 0.6243(2) 0.23154(7) 0.45478(19) 0.0366(3) Uani 1 1 d . . . . .
O4 O 0.3734(2) 0.34350(8) 0.1529(3) 0.0474(4) Uani 1 1 d . . . . .
O1 O 0.3821(2) 0.27451(9) 0.5902(2) 0.0466(4) Uani 1 1 d . . . . .
N2 N 0.3009(2) 0.39210(7) 0.2178(2) 0.0265(3) Uani 1 1 d . . . . .
N1 N 0.5542(2) 0.27318(8) 0.5516(2) 0.0299(3) Uani 1 1 d . . . . .
C7 C 0.8252(2) 0.57994(8) 0.5413(2) 0.0212(3) Uani 1 1 d . . . . .
C6 C 0.6813(2) 0.53303(8) 0.4553(2) 0.0206(3) Uani 1 1 d . . . . .
C2 C 0.6315(2) 0.43626(8) 0.2716(2) 0.0228(3) Uani 1 1 d . . . . .
H2 H 0.680684 0.401539 0.201438 0.027 Uiso 1 1 calc R . . . .
C17 C 0.9266(2) 0.42134(7) 0.7655(2) 0.0217(3) Uani 1 1 d . . . . .
C19 C 0.6049(2) 0.37441(9) 0.7282(2) 0.0242(3) Uani 1 1 d . . . . .
H19 H 0.469777 0.374677 0.751183 0.029 Uiso 1 1 calc R . . . .
C16 C 1.0652(2) 0.47188(8) 0.8415(2) 0.0230(3) Uani 1 1 d . . . . .
C11 C 1.1095(2) 0.76833(8) 0.9418(2) 0.0249(3) Uani 1 1 d . . . . .
H11A H 1.073828 0.774335 0.810740 0.030 Uiso 1 1 calc R . . . .
H11B H 1.134278 0.811608 0.998022 0.030 Uiso 1 1 calc R . . . .
C3 C 0.7551(2) 0.48290(8) 0.3498(2) 0.0222(3) Uani 1 1 d . . . . .
H3 H 0.891185 0.480783 0.331615 0.027 Uiso 1 1 calc R . . . .
C18 C 0.7276(2) 0.42340(8) 0.7963(2) 0.0228(3) Uani 1 1 d . . . . .
H18 H 0.675927 0.458358 0.863897 0.027 Uiso 1 1 calc R . . . .
C14 C 0.9594(2) 0.62507(8) 1.0604(2) 0.0238(3) Uani 1 1 d . . . . .
H14 H 0.867710 0.603155 1.142769 0.029 Uiso 1 1 calc R . . . .
C4 C 0.3551(2) 0.49161(8) 0.3998(2) 0.0249(3) Uani 1 1 d . . . . .
H4 H 0.218486 0.494194 0.414719 0.030 Uiso 1 1 calc R . . . .
C21 C 0.8804(2) 0.32282(8) 0.5891(2) 0.0229(3) Uani 1 1 d . . . . .
H21 H 0.930268 0.288969 0.516248 0.027 Uiso 1 1 calc R . . . .
C9 C 0.8436(2) 0.67460(8) 0.9345(2) 0.0234(3) Uani 1 1 d . . . . .
H9 H 0.702453 0.673977 0.962999 0.028 Uiso 1 1 calc R . . . .
C20 C 0.6844(2) 0.32506(8) 0.6259(2) 0.0236(3) Uani 1 1 d . . . . .
C22 C 1.0020(3) 0.37123(8) 0.6613(2) 0.0232(3) Uani 1 1 d . . . . .
H22 H 1.137468 0.370278 0.639788 0.028 Uiso 1 1 calc R . . . .
C12 C 1.2876(3) 0.72464(8) 0.9677(2) 0.0276(3) Uani 1 1 d . . . . .
H12A H 1.293079 0.692977 0.866360 0.033 Uiso 1 1 calc R . . . .
H12B H 1.408729 0.750924 0.972381 0.033 Uiso 1 1 calc R . . . .
C1 C 0.4333(2) 0.44191(8) 0.2989(2) 0.0224(3) Uani 1 1 d . . . . .
C5 C 0.4819(2) 0.53789(8) 0.4792(2) 0.0239(3) Uani 1 1 d . . . . .
H5 H 0.432238 0.572561 0.549155 0.029 Uiso 1 1 calc R . . . .
C10 C 0.9486(2) 0.73239(8) 1.0372(2) 0.0244(3) Uani 1 1 d . . . . .
H10 H 0.858779 0.761665 1.102689 0.029 Uiso 1 1 calc R . . . .
C13 C 1.0622(2) 0.68311(8) 1.1631(2) 0.0250(3) Uani 1 1 d . . . . .
H13 H 1.027811 0.686364 1.293625 0.030 Uiso 1 1 calc R . . . .
C15 C 1.0937(2) 0.57500(8) 0.9839(2) 0.0257(3) Uani 1 1 d . . . . .
H15A H 1.168933 0.594301 0.885546 0.031 Uiso 1 1 calc R . . . .
H15B H 1.186596 0.558602 1.080554 0.031 Uiso 1 1 calc R . . . .
C8 C 0.8628(2) 0.67438(8) 0.7305(2) 0.0250(3) Uani 1 1 d . . . . .
H8A H 0.821868 0.717156 0.679202 0.030 Uiso 1 1 calc R . . . .
H8B H 1.000668 0.666951 0.702102 0.030 Uiso 1 1 calc R . . . .
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
C16 O8 C15 115.34(13) . . ?
C7 O6 C8 117.56(13) . . ?
C13 O9 C12 108.29(12) . . ?
O3 N2 C1 118.24(14) . . ?
O4 N2 O3 123.78(15) . . ?
O4 N2 C1 117.98(14) . . ?
O2 N1 O1 123.94(16) . . ?
O2 N1 C20 118.04(14) . . ?
O1 N1 C20 118.01(15) . . ?
O5 C7 O6 124.89(15) . . ?
O5 C7 C6 122.98(14) . . ?
O6 C7 C6 112.13(13) . . ?
C3 C6 C7 117.23(14) . . ?
C5 C6 C7 122.27(14) . . ?
C5 C6 C3 120.50(15) . . ?
C3 C2 H2 121.1 . . ?
C3 C2 C1 117.82(15) . . ?
C1 C2 H2 121.1 . . ?
C18 C17 C16 121.85(14) . . ?
C18 C17 C22 120.15(15) . . ?
C22 C17 C16 118.00(14) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C20 C19 C18 118.42(15) . . ?
O8 C16 C17 111.51(14) . . ?
O7 C16 O8 124.54(15) . . ?
O7 C16 C17 123.94(15) . . ?
H11A C11 H11B 108.9 . . ?
C12 C11 H11A 110.8 . . ?
C12 C11 H11B 110.8 . . ?
C12 C11 C10 104.62(13) . . ?
C10 C11 H11A 110.8 . . ?
C10 C11 H11B 110.8 . . ?
C6 C3 H3 119.8 . . ?
C2 C3 C6 120.48(14) . . ?
C2 C3 H3 119.8 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.05(15) . . ?
C19 C18 H18 120.0 . . ?
C9 C14 H14 109.4 . . ?
C13 C14 H14 109.4 . . ?
C13 C14 C9 89.75(11) . . ?
C15 C14 H14 109.4 . . ?
C15 C14 C9 121.68(13) . . ?
C15 C14 C13 115.49(14) . . ?
C1 C4 H4 120.8 . . ?
C1 C4 C5 118.33(14) . . ?
C5 C4 H4 120.8 . . ?
C20 C21 H21 120.9 . . ?
C20 C21 C22 118.29(15) . . ?
C22 C21 H21 120.9 . . ?
C14 C9 H9 109.8 . . ?
C10 C9 C14 89.87(12) . . ?
C10 C9 H9 109.8 . . ?
C8 C9 C14 121.22(13) . . ?
C8 C9 H9 109.8 . . ?
C8 C9 C10 114.90(13) . . ?
C19 C20 N1 118.66(14) . . ?
C21 C20 N1 118.65(14) . . ?
C21 C20 C19 122.68(16) . . ?
C17 C22 H22 119.8 . . ?
C21 C22 C17 120.36(15) . . ?
C21 C22 H22 119.8 . . ?
O9 C12 C11 105.73(14) . . ?
O9 C12 H12A 110.6 . . ?
O9 C12 H12B 110.6 . . ?
C11 C12 H12A 110.6 . . ?
C11 C12 H12B 110.6 . . ?
H12A C12 H12B 108.7 . . ?
C2 C1 N2 118.19(14) . . ?
C4 C1 N2 118.68(14) . . ?
C4 C1 C2 123.12(15) . . ?
C6 C5 C4 119.73(14) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C11 C10 C9 118.21(13) . . ?
C11 C10 H10 114.0 . . ?
C11 C10 C13 103.56(13) . . ?
C9 C10 H10 114.0 . . ?
C13 C10 C9 90.04(12) . . ?
C13 C10 H10 114.0 . . ?
O9 C13 C14 116.74(13) . . ?
O9 C13 C10 108.12(13) . . ?
O9 C13 H13 113.1 . . ?
C14 C13 H13 113.1 . . ?
C10 C13 C14 90.34(12) . . ?
C10 C13 H13 113.1 . . ?
O8 C15 C14 106.62(13) . . ?
O8 C15 H15A 110.4 . . ?
O8 C15 H15B 110.4 . . ?
C14 C15 H15A 110.4 . . ?
C14 C15 H15B 110.4 . . ?
H15A C15 H15B 108.6 . . ?
O6 C8 C9 109.52(13) . . ?
O6 C8 H8A 109.8 . . ?
O6 C8 H8B 109.8 . . ?
C9 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
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
O8 C16 1.338(2) . ?
O8 C15 1.4578(19) . ?
O5 C7 1.213(2) . ?
O6 C7 1.334(2) . ?
O6 C8 1.4602(19) . ?
O7 C16 1.211(2) . ?
O9 C12 1.438(2) . ?
O9 C13 1.425(2) . ?
O3 N2 1.2268(19) . ?
O2 N1 1.224(2) . ?
O4 N2 1.221(2) . ?
O1 N1 1.228(2) . ?
N2 C1 1.474(2) . ?
N1 C20 1.477(2) . ?
C7 C6 1.497(2) . ?
C6 C3 1.397(2) . ?
C6 C5 1.390(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(2) . ?
C2 C1 1.389(2) . ?
C17 C16 1.497(2) . ?
C17 C18 1.396(2) . ?
C17 C22 1.395(2) . ?
C19 H19 0.9500 . ?
C19 C18 1.388(2) . ?
C19 C20 1.387(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.519(2) . ?
C11 C10 1.525(2) . ?
C3 H3 0.9500 . ?
C18 H18 0.9500 . ?
C14 H14 1.0000 . ?
C14 C9 1.565(2) . ?
C14 C13 1.560(2) . ?
C14 C15 1.506(2) . ?
C4 H4 0.9500 . ?
C4 C1 1.383(2) . ?
C4 C5 1.396(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.385(2) . ?
C21 C22 1.386(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.562(2) . ?
C9 C8 1.511(2) . ?
C22 H22 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C5 H5 0.9500 . ?
C10 H10 1.0000 . ?
C10 C13 1.554(2) . ?
C13 H13 1.0000 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
