#------------------------------------------------------------------------------
#$Date: 2023-01-06 12:06:30 +0200 (Fri, 06 Jan 2023) $
#$Revision: 280224 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/76/1567626.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_1567626
loop_
_publ_author_name
'Koo, Bonwoo'
'Kim, Dopil'
'Song, Da Yong'
'Han, Woo Joo'
'Kim, Dongwook'
'Park, Jae Woo'
'Kim, Min'
'Kim, Cheoljae'
_publ_section_title
;
 The formation of photodegradable nitrophenylene polymers via ring-opening
 metathesis polymerization
;
_journal_issue                   45
_journal_name_full               'Polymer Chemistry'
_journal_page_first              6268
_journal_page_last               6273
_journal_paper_doi               10.1039/D2PY00684G
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C16 H17 N O6'
_chemical_formula_sum            'C16 H17 N O6'
_chemical_formula_weight         319.30
_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     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-02-09 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.4138(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1387(4)
_cell_length_b                   24.2934(10)
_cell_length_c                   8.5069(4)
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.94
_cell_volume                     1493.08(12)
_computing_cell_refinement       'Bruker APEXIII'
_computing_data_collection       'Bruker APEXIII'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_computing_structure_refinement  SHELXL
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            34884
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.293
_diffrn_reflns_theta_min         2.825
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0443
_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)+(0.0542P)²+0.6173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1190
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3286
_reflns_number_total             3658
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2py00684g2.cif
_cod_data_source_block           032_014
_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/rss-feeds/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 

 Adding full bibliography for 1567622--1567627.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1567626
_shelx_shelxl_version_number     2018/3
_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   0.977
_shelx_estimated_absorpt_t_max   0.986
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
C1 C 0.35475(17) 0.39629(5) 0.49281(17) 0.0270(2) Uani 1 1 d . . . . .
C2 C 0.47791(17) 0.42192(5) 0.65126(16) 0.0262(2) Uani 1 1 d . . . . .
C3 C 0.43535(19) 0.47635(5) 0.67545(17) 0.0298(3) Uani 1 1 d . . . . .
C4 C 0.2805(2) 0.50405(5) 0.5534(2) 0.0369(3) Uani 1 1 d . . . . .
H4 H 0.256877 0.540818 0.575294 0.044 Uiso 1 1 calc R U . . .
C5 C 0.1611(2) 0.47765(6) 0.3998(2) 0.0400(3) Uani 1 1 d . . . . .
H5 H 0.053843 0.496005 0.314862 0.048 Uiso 1 1 calc R U . . .
C6 C 0.19845(19) 0.42418(6) 0.36995(18) 0.0341(3) Uani 1 1 d . . . . .
H6 H 0.115948 0.406100 0.263634 0.041 Uiso 1 1 calc R U . . .
C7 C 0.3877(2) 0.33951(5) 0.44205(19) 0.0322(3) Uani 1 1 d . . . . .
H7A H 0.453112 0.316213 0.548531 0.039 Uiso 1 1 calc R U . . .
H7B H 0.268972 0.321624 0.361997 0.039 Uiso 1 1 calc R U . . .
O8 O 0.50109(13) 0.34768(3) 0.35255(12) 0.0301(2) Uani 1 1 d . . . . .
O9 O 0.49099(15) 0.25692(4) 0.30395(14) 0.0362(2) Uani 1 1 d . . . . .
C10 C 0.54065(16) 0.30217(5) 0.28712(15) 0.0247(2) Uani 1 1 d . . . . .
C11 C 0.65499(18) 0.31475(5) 0.19472(16) 0.0284(3) Uani 1 1 d . . . . .
H11A H 0.656703 0.355014 0.177548 0.034 Uiso 1 1 calc R U . . .
H11B H 0.598372 0.297105 0.076548 0.034 Uiso 1 1 calc R U . . .
C12 C 0.85286(19) 0.29394(6) 0.30186(18) 0.0337(3) Uani 1 1 d . . . . .
H12A H 0.850320 0.253922 0.322653 0.040 Uiso 1 1 calc R U . . .
H12B H 0.921666 0.299640 0.232849 0.040 Uiso 1 1 calc R U . . .
C13 C 0.95312(18) 0.32320(5) 0.47855(19) 0.0331(3) Uani 1 1 d . . . . .
H13 H 0.923282 0.360731 0.483819 0.040 Uiso 1 1 calc R U . . .
C14 C 1.07781(18) 0.30045(5) 0.62435(18) 0.0330(3) Uani 1 1 d . . . . .
H14 H 1.099633 0.262223 0.619357 0.040 Uiso 1 1 calc R U . . .
C15 C 1.18927(18) 0.32854(6) 0.79780(18) 0.0344(3) Uani 1 1 d . . . . .
H15A H 1.314625 0.335509 0.810435 0.041 Uiso 1 1 calc R U . . .
H15B H 1.202997 0.302886 0.893525 0.041 Uiso 1 1 calc R U . . .
C16 C 1.11250(17) 0.38282(5) 0.82645(19) 0.0327(3) Uani 1 1 d . . . . .
H16A H 1.211662 0.402942 0.926260 0.039 Uiso 1 1 calc R U . . .
H16B H 1.071172 0.405888 0.718957 0.039 Uiso 1 1 calc R U . . .
C17 C 0.95261(17) 0.37337(5) 0.86588(16) 0.0282(3) Uani 1 1 d . . . . .
O18 O 0.96218(15) 0.34658(5) 0.98886(14) 0.0428(3) Uani 1 1 d . . . . .
O19 O 0.79566(12) 0.39799(4) 0.75015(12) 0.0298(2) Uani 1 1 d . . . . .
C20 C 0.64037(18) 0.39086(5) 0.78877(18) 0.0311(3) Uani 1 1 d . . . . .
H20A H 0.672519 0.405240 0.908335 0.037 Uiso 1 1 calc R U . . .
H20B H 0.609514 0.351312 0.785342 0.037 Uiso 1 1 calc R U . . .
N21 N 0.55794(19) 0.50826(5) 0.83422(17) 0.0377(3) Uani 1 1 d . . . . .
O22 O 0.48633(19) 0.54517(4) 0.88106(16) 0.0496(3) Uani 1 1 d . . . . .
O23 O 0.72318(16) 0.49758(5) 0.91000(16) 0.0510(3) 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.43(11) . . ?
C6 C1 C7 116.83(12) . . ?
C2 C1 C7 122.66(12) . . ?
C1 C2 C3 116.31(11) . . ?
C1 C2 C20 120.55(11) . . ?
C3 C2 C20 123.08(12) . . ?
C4 C3 C2 123.25(12) . . ?
C4 C3 N21 115.44(12) . . ?
C2 C3 N21 121.30(12) . . ?
C5 C4 C3 119.13(12) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 119.55(13) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 121.32(13) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
O8 C7 C1 105.34(9) . . ?
O8 C7 H7A 110.7 . . ?
C1 C7 H7A 110.7 . . ?
O8 C7 H7B 110.7 . . ?
C1 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C10 O8 C7 115.83(9) . . ?
O9 C10 O8 123.09(11) . . ?
O9 C10 C11 124.90(11) . . ?
O8 C10 C11 112.01(10) . . ?
C10 C11 C12 110.99(10) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 112.02(11) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 124.72(12) . . ?
C14 C13 H13 117.6 . . ?
C12 C13 H13 117.6 . . ?
C13 C14 C15 126.58(12) . . ?
C13 C14 H14 116.7 . . ?
C15 C14 H14 116.7 . . ?
C14 C15 C16 116.44(11) . . ?
C14 C15 H15A 108.2 . . ?
C16 C15 H15A 108.2 . . ?
C14 C15 H15B 108.2 . . ?
C16 C15 H15B 108.2 . . ?
H15A C15 H15B 107.3 . . ?
C17 C16 C15 111.33(11) . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
O18 C17 O19 122.51(12) . . ?
O18 C17 C16 124.06(12) . . ?
O19 C17 C16 113.43(11) . . ?
C17 O19 C20 114.44(10) . . ?
O19 C20 C2 107.98(9) . . ?
O19 C20 H20A 110.1 . . ?
C2 C20 H20A 110.1 . . ?
O19 C20 H20B 110.1 . . ?
C2 C20 H20B 110.1 . . ?
H20A C20 H20B 108.4 . . ?
O23 N21 O22 123.63(13) . . ?
O23 N21 C3 119.15(11) . . ?
O22 N21 C3 117.21(13) . . ?
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 C6 1.3946(19) . ?
C1 C2 1.4018(18) . ?
C1 C7 1.5060(17) . ?
C2 C3 1.4057(17) . ?
C2 C20 1.5040(18) . ?
C3 C4 1.384(2) . ?
C3 N21 1.4765(18) . ?
C4 C5 1.376(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O8 1.4554(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O8 C10 1.3418(14) . ?
O9 C10 1.2024(15) . ?
C10 C11 1.5003(17) . ?
C11 C12 1.5259(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5169(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.3094(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.4944(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.5262(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5035(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O18 1.2038(16) . ?
C17 O19 1.3418(15) . ?
O19 C20 1.4552(14) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
N21 O23 1.2219(18) . ?
N21 O22 1.2314(16) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.89(17) . . . . ?
C7 C1 C2 C3 175.91(10) . . . . ?
C6 C1 C2 C20 176.35(11) . . . . ?
C7 C1 C2 C20 -6.84(17) . . . . ?
C1 C2 C3 C4 0.78(17) . . . . ?
C20 C2 C3 C4 -176.40(11) . . . . ?
C1 C2 C3 N21 -177.92(10) . . . . ?
C20 C2 C3 N21 4.91(17) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
N21 C3 C4 C5 178.59(12) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C2 C1 C6 C5 0.45(19) . . . . ?
C7 C1 C6 C5 -176.53(12) . . . . ?
C6 C1 C7 O8 90.11(13) . . . . ?
C2 C1 C7 O8 -86.80(14) . . . . ?
C1 C7 O8 C10 -176.86(10) . . . . ?
C7 O8 C10 O9 -1.89(17) . . . . ?
C7 O8 C10 C11 178.99(10) . . . . ?
O9 C10 C11 C12 -70.24(16) . . . . ?
O8 C10 C11 C12 108.86(12) . . . . ?
C10 C11 C12 C13 -64.13(14) . . . . ?
C11 C12 C13 C14 146.67(13) . . . . ?
C12 C13 C14 C15 175.48(12) . . . . ?
C13 C14 C15 C16 20.3(2) . . . . ?
C14 C15 C16 C17 75.73(15) . . . . ?
C15 C16 C17 O18 58.82(17) . . . . ?
C15 C16 C17 O19 -121.35(12) . . . . ?
O18 C17 O19 C20 1.66(17) . . . . ?
C16 C17 O19 C20 -178.17(10) . . . . ?
C17 O19 C20 C2 178.43(10) . . . . ?
C1 C2 C20 O19 89.29(13) . . . . ?
C3 C2 C20 O19 -93.66(13) . . . . ?
C4 C3 N21 O23 -151.17(13) . . . . ?
C2 C3 N21 O23 27.62(17) . . . . ?
C4 C3 N21 O22 27.73(16) . . . . ?
C2 C3 N21 O22 -153.48(12) . . . . ?
