#------------------------------------------------------------------------------
#$Date: 2023-01-06 12:06:30 +0200 (Fri, 06 Jan 2023) $
#$Revision: 280224 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/76/1567624.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_1567624
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         'C18 H21 N O6'
_chemical_formula_sum            'C18 H21 N O6'
_chemical_formula_weight         347.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 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                 97.379(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0300(3)
_cell_length_b                   20.5537(12)
_cell_length_c                   16.8829(10)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      3.14
_cell_volume                     1730.99(18)
_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 0.983
_diffrn_measurement_device_type  'PHOTON II 14'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10870
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.992
_diffrn_reflns_theta_min         3.139
_diffrn_source                   'I\^I1/4S 3.0 Microfocus'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       rod
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 1228 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3487
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0782
_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)+(0.1483P)²+0.7620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2076
_refine_ls_wR_factor_ref         0.2152
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.891
_reflns_Friedel_fraction_max     0.856
_reflns_number_gt                3186
_reflns_number_total             3487
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2py00684g2.cif
_cod_data_source_block           031_009
_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_cell_volume        1730.98(18)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1567624
_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   0.974
_shelx_estimated_absorpt_t_max   0.995
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'
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 0.4030(9) 0.7123(2) 0.4041(3) 0.0279(9) Uani 1 1 d . . . . .
C2 C 0.5757(9) 0.7563(2) 0.3735(3) 0.0290(10) Uani 1 1 d . . . . .
C3 C 0.6313(12) 0.7547(2) 0.2953(3) 0.0365(11) Uani 1 1 d . . . . .
H3 H 0.750941 0.785334 0.277001 0.044 Uiso 1 1 calc R U . . .
C4 C 0.5109(13) 0.7081(2) 0.2448(3) 0.0396(12) Uani 1 1 d . . . . .
H4 H 0.547009 0.705990 0.190942 0.048 Uiso 1 1 calc R U . . .
C5 C 0.3350(12) 0.6639(2) 0.2729(3) 0.0389(12) Uani 1 1 d . . . . .
H5 H 0.250050 0.631919 0.237660 0.047 Uiso 1 1 calc R U . . .
C6 C 0.2812(9) 0.6656(2) 0.3521(3) 0.0299(10) Uani 1 1 d . . . . .
C7 C 0.0832(10) 0.6163(2) 0.3771(3) 0.0336(10) Uani 1 1 d . . . . .
H7A H -0.075685 0.639622 0.391589 0.040 Uiso 1 1 calc R U . . .
H7B H 0.022584 0.587783 0.330973 0.040 Uiso 1 1 calc R U . . .
O8 O 0.1930(6) 0.57622(15) 0.4437(2) 0.0305(7) Uani 1 1 d . . . . .
O9 O 0.4611(8) 0.52805(19) 0.3650(2) 0.0413(9) Uani 1 1 d . . . . .
C10 C 0.3843(8) 0.5323(2) 0.4279(3) 0.0276(9) Uani 1 1 d . . . . .
C11 C 0.4686(9) 0.4917(2) 0.5012(3) 0.0267(9) Uani 1 1 d . . . . .
H11A H 0.320318 0.461827 0.509696 0.032 Uiso 1 1 calc R U . . .
H11B H 0.500297 0.520716 0.548284 0.032 Uiso 1 1 calc R U . . .
C12 C 0.7195(9) 0.4520(2) 0.4957(3) 0.0289(9) Uani 1 1 d . . . . .
H12A H 0.863162 0.480793 0.480957 0.035 Uiso 1 1 calc R U . . .
H12B H 0.682084 0.418627 0.453444 0.035 Uiso 1 1 calc R U . . .
C13 C 0.8150(11) 0.4183(2) 0.5770(3) 0.0349(10) Uani 1 1 d . . . . .
H13A H 0.663432 0.393949 0.594777 0.042 Uiso 1 1 calc R U . . .
H13B H 0.958381 0.386671 0.569715 0.042 Uiso 1 1 calc R U . . .
C14 C 0.9180(10) 0.4662(2) 0.6397(3) 0.0334(10) Uani 1 1 d . . . . .
H14 H 1.089000 0.484741 0.635982 0.040 Uiso 1 1 calc R U . . .
C15 C 0.7933(11) 0.4854(2) 0.6999(3) 0.0338(10) Uani 1 1 d . . . . .
H15 H 0.635248 0.462668 0.708709 0.041 Uiso 1 1 calc R U . . .
C16 C 0.8834(10) 0.5406(2) 0.7557(3) 0.0333(10) Uani 1 1 d . . . . .
H16A H 1.074693 0.550225 0.752809 0.040 Uiso 1 1 calc R U . . .
H16B H 0.864426 0.527889 0.811263 0.040 Uiso 1 1 calc R U . . .
C17 C 0.7142(10) 0.6012(2) 0.7327(3) 0.0318(10) Uani 1 1 d . . . . .
H17A H 0.748518 0.634022 0.775695 0.038 Uiso 1 1 calc R U . . .
H17B H 0.521793 0.589477 0.727439 0.038 Uiso 1 1 calc R U . . .
C18 C 0.7784(10) 0.6308(2) 0.6536(3) 0.0287(9) Uani 1 1 d . . . . .
H18A H 0.945869 0.656433 0.664188 0.034 Uiso 1 1 calc R U . . .
H18B H 0.810519 0.595109 0.616667 0.034 Uiso 1 1 calc R U . . .
C19 C 0.5614(9) 0.6738(2) 0.6136(3) 0.0276(9) Uani 1 1 d . . . . .
O20 O 0.3999(9) 0.7033(2) 0.6464(2) 0.0488(11) Uani 1 1 d . . . . .
O21 O 0.5610(7) 0.67513(17) 0.53482(19) 0.0332(8) Uani 1 1 d . . . . .
C22 C 0.3515(10) 0.7143(2) 0.4906(3) 0.0335(10) Uani 1 1 d . . . . .
H22A H 0.359729 0.759666 0.510659 0.040 Uiso 1 1 calc R U . . .
H22B H 0.172502 0.696213 0.496184 0.040 Uiso 1 1 calc R U . . .
N23 N 0.7072(10) 0.8085(2) 0.4235(3) 0.0406(11) Uani 1 1 d . . . . .
O24 O 0.7093(16) 0.8629(2) 0.3948(3) 0.083(2) Uani 1 1 d . . . . .
O25 O 0.8012(11) 0.7971(2) 0.4928(3) 0.0593(13) 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 117.3(4) . . ?
C6 C1 C22 120.8(4) . . ?
C2 C1 C22 121.9(4) . . ?
C3 C2 C1 123.3(4) . . ?
C3 C2 N23 115.7(4) . . ?
C1 C2 N23 121.0(4) . . ?
C4 C3 C2 118.9(5) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 119.5(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 121.2(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 119.9(4) . . ?
C1 C6 C7 122.6(4) . . ?
C5 C6 C7 117.5(4) . . ?
O8 C7 C6 113.4(4) . . ?
O8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
O8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C10 O8 C7 115.5(4) . . ?
O9 C10 O8 123.0(4) . . ?
O9 C10 C11 127.5(4) . . ?
O8 C10 C11 109.6(4) . . ?
C10 C11 C12 113.3(4) . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 110.5(4) . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 111.8(4) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 126.0(5) . . ?
C15 C14 H14 117.0 . . ?
C13 C14 H14 117.0 . . ?
C14 C15 C16 124.8(5) . . ?
C14 C15 H15 117.6 . . ?
C16 C15 H15 117.6 . . ?
C15 C16 C17 110.0(4) . . ?
C15 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C16 C17 C18 111.7(4) . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 C17 113.7(4) . . ?
C19 C18 H18A 108.8 . . ?
C17 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
O20 C19 O21 122.3(4) . . ?
O20 C19 C18 125.9(4) . . ?
O21 C19 C18 111.7(4) . . ?
C19 O21 C22 115.6(4) . . ?
O21 C22 C1 106.0(4) . . ?
O21 C22 H22A 110.5 . . ?
C1 C22 H22A 110.5 . . ?
O21 C22 H22B 110.5 . . ?
C1 C22 H22B 110.5 . . ?
H22A C22 H22B 108.7 . . ?
O24 N23 O25 122.2(5) . . ?
O24 N23 C2 117.9(4) . . ?
O25 N23 C2 119.8(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 C6 1.388(7) . ?
C1 C2 1.398(7) . ?
C1 C22 1.517(7) . ?
C2 C3 1.384(7) . ?
C2 N23 1.471(6) . ?
C3 C4 1.371(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.518(7) . ?
C7 O8 1.445(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O8 C10 1.370(5) . ?
O9 C10 1.179(6) . ?
C10 C11 1.509(6) . ?
C11 C12 1.516(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.558(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.489(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.322(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.506(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.531(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.539(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.496(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O20 1.204(6) . ?
C19 O21 1.331(5) . ?
O21 C22 1.454(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
N23 O24 1.218(6) . ?
N23 O25 1.227(6) . ?
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 -0.8(7) . . . . ?
C22 C1 C2 C3 178.5(4) . . . . ?
C6 C1 C2 N23 178.2(4) . . . . ?
C22 C1 C2 N23 -2.5(7) . . . . ?
C1 C2 C3 C4 0.4(8) . . . . ?
N23 C2 C3 C4 -178.6(5) . . . . ?
C2 C3 C4 C5 0.3(8) . . . . ?
C3 C4 C5 C6 -0.7(8) . . . . ?
C2 C1 C6 C5 0.4(6) . . . . ?
C22 C1 C6 C5 -178.9(4) . . . . ?
C2 C1 C6 C7 -178.1(4) . . . . ?
C22 C1 C6 C7 2.5(6) . . . . ?
C4 C5 C6 C1 0.3(7) . . . . ?
C4 C5 C6 C7 179.0(5) . . . . ?
C1 C6 C7 O8 -58.3(6) . . . . ?
C5 C6 C7 O8 123.1(5) . . . . ?
C6 C7 O8 C10 -69.7(5) . . . . ?
C7 O8 C10 O9 1.8(6) . . . . ?
C7 O8 C10 C11 -176.9(3) . . . . ?
O9 C10 C11 C12 13.8(7) . . . . ?
O8 C10 C11 C12 -167.6(4) . . . . ?
C10 C11 C12 C13 172.9(4) . . . . ?
C11 C12 C13 C14 -68.9(5) . . . . ?
C12 C13 C14 C15 105.8(6) . . . . ?
C13 C14 C15 C16 -171.0(4) . . . . ?
C14 C15 C16 C17 101.6(6) . . . . ?
C15 C16 C17 C18 -70.5(5) . . . . ?
C16 C17 C18 C19 159.4(4) . . . . ?
C17 C18 C19 O20 26.3(7) . . . . ?
C17 C18 C19 O21 -152.3(4) . . . . ?
O20 C19 O21 C22 -0.4(7) . . . . ?
C18 C19 O21 C22 178.4(4) . . . . ?
C19 O21 C22 C1 176.1(4) . . . . ?
C6 C1 C22 O21 92.2(5) . . . . ?
C2 C1 C22 O21 -87.1(5) . . . . ?
C3 C2 N23 O24 43.9(8) . . . . ?
C1 C2 N23 O24 -135.1(6) . . . . ?
C3 C2 N23 O25 -138.8(6) . . . . ?
C1 C2 N23 O25 42.1(8) . . . . ?
