#------------------------------------------------------------------------------
#$Date: 2023-01-06 12:06:30 +0200 (Fri, 06 Jan 2023) $
#$Revision: 280224 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/76/1567625.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_1567625
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           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                 106.541(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.150(4)
_cell_length_b                   9.733(3)
_cell_length_c                   10.702(3)
_cell_measurement_reflns_used    9526
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.02
_cell_measurement_theta_min      2.88
_cell_volume                     1712.5(8)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.1536
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20258
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.478
_diffrn_source                   'I\^I1/4S 3.0 Microfocus'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.3322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.182
_refine_ls_R_factor_all          0.1464
_refine_ls_R_factor_gt           0.1112
_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)+(0.0475P)²+4.6038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2192
_refine_ls_wR_factor_ref         0.2349
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2327
_reflns_number_total             3188
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2py00684g2.cif
_cod_data_source_block           033_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_cell_volume        1712.6(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1567625
_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   0.987
_shelx_estimated_absorpt_t_max   0.997
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 0.3831(3) 0.3716(5) 0.4416(4) 0.0291(10) Uani 1 1 d . . . . .
C2 C 0.3494(3) 0.4503(5) 0.3303(5) 0.0328(11) Uani 1 1 d . . . . .
H2 H 0.329220 0.404389 0.249136 0.039 Uiso 1 1 calc R U . . .
C3 C 0.3441(3) 0.5924(5) 0.3327(5) 0.0363(12) Uani 1 1 d . . . . .
H3 H 0.320304 0.640971 0.254098 0.044 Uiso 1 1 calc R U . . .
C4 C 0.3731(3) 0.6647(5) 0.4486(5) 0.0320(11) Uani 1 1 d . . . . .
C5 C 0.4104(3) 0.5913(5) 0.5601(5) 0.0314(11) Uani 1 1 d . . . . .
H5 H 0.432403 0.638235 0.640259 0.038 Uiso 1 1 calc R U . . .
C6 C 0.4157(2) 0.4501(5) 0.5556(4) 0.0290(10) Uani 1 1 d . . . . .
C7 C 0.3817(3) 0.2171(5) 0.4328(5) 0.0354(11) Uani 1 1 d . . . . .
H7A H 0.437835 0.182336 0.446964 0.042 Uiso 1 1 calc R U . . .
H7B H 0.360061 0.178464 0.501761 0.042 Uiso 1 1 calc R U . . .
O8 O 0.33180(18) 0.1734(3) 0.3070(3) 0.0366(8) Uani 1 1 d . . . . .
O9 O 0.2230(2) 0.1767(4) 0.3837(3) 0.0433(9) Uani 1 1 d . . . . .
C10 C 0.2512(3) 0.1599(5) 0.2956(5) 0.0325(11) Uani 1 1 d . . . . .
C11 C 0.2051(3) 0.1161(5) 0.1583(5) 0.0373(12) Uani 1 1 d . . . . .
H11A H 0.212888 0.016121 0.149714 0.045 Uiso 1 1 calc R U . . .
H11B H 0.228969 0.163450 0.096062 0.045 Uiso 1 1 calc R U . . .
C12 C 0.1140(3) 0.1462(6) 0.1203(5) 0.0430(13) Uani 1 1 d . . . . .
H12A H 0.086048 0.081521 0.050567 0.052 Uiso 1 1 calc R U . . .
H12B H 0.093803 0.128242 0.196677 0.052 Uiso 1 1 calc R U . . .
C13 C 0.0908(3) 0.2921(6) 0.0732(5) 0.0452(14) Uani 1 1 d . . . . .
H13A H 0.113696 0.311680 -0.000086 0.054 Uiso 1 1 calc R U . . .
H13B H 0.030864 0.297367 0.038940 0.054 Uiso 1 1 calc R U . . .
C14 C 0.1193(3) 0.4030(6) 0.1756(6) 0.0501(15) Uani 1 1 d . . . . .
H14 H 0.175660 0.402058 0.220796 0.060 Uiso 1 1 calc R U . . .
C15 C 0.0773(3) 0.4983(6) 0.2098(6) 0.0498(14) Uani 1 1 d . . . . .
H15 H 0.021149 0.504214 0.163944 0.060 Uiso 1 1 calc R U . . .
C16 C 0.1104(4) 0.6000(5) 0.3157(5) 0.0473(14) Uani 1 1 d . . . . .
H16A H 0.167334 0.575110 0.361252 0.057 Uiso 1 1 calc R U . . .
H16B H 0.078685 0.593719 0.379690 0.057 Uiso 1 1 calc R U . . .
C17 C 0.1083(3) 0.7470(5) 0.2689(5) 0.0386(12) Uani 1 1 d . . . . .
H17A H 0.051682 0.771254 0.220421 0.046 Uiso 1 1 calc R U . . .
H17B H 0.141979 0.754674 0.207938 0.046 Uiso 1 1 calc R U . . .
C18 C 0.1395(3) 0.8495(5) 0.3810(5) 0.0377(12) Uani 1 1 d . . . . .
H18A H 0.136364 0.943733 0.345213 0.045 Uiso 1 1 calc R U . . .
H18B H 0.104328 0.845303 0.439950 0.045 Uiso 1 1 calc R U . . .
C19 C 0.2255(3) 0.8190(5) 0.4570(5) 0.0348(11) Uani 1 1 d . . . . .
O20 O 0.2472(2) 0.7661(4) 0.5625(3) 0.0466(10) Uani 1 1 d . . . . .
O21 O 0.27852(19) 0.8556(3) 0.3897(3) 0.0376(8) Uani 1 1 d . . . . .
C22 C 0.3633(3) 0.8173(5) 0.4499(5) 0.0365(12) Uani 1 1 d . . . . .
H22A H 0.380862 0.851048 0.540863 0.044 Uiso 1 1 calc R U . . .
H22B H 0.398224 0.860846 0.401676 0.044 Uiso 1 1 calc R U . . .
N23 N 0.4605(2) 0.3813(4) 0.6787(4) 0.0354(10) Uani 1 1 d . . . . .
O24 O 0.4851(2) 0.4539(4) 0.7770(3) 0.0444(9) Uani 1 1 d . . . . .
O25 O 0.4723(2) 0.2588(4) 0.6770(3) 0.0475(10) 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
C2 C1 C6 114.0(4) . . ?
C2 C1 C7 120.0(4) . . ?
C6 C1 C7 126.1(4) . . ?
C3 C2 C1 123.0(5) . . ?
C3 C2 H2 118.5 . . ?
C1 C2 H2 118.5 . . ?
C2 C3 C4 120.9(5) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.0(4) . . ?
C5 C4 C22 122.1(4) . . ?
C3 C4 C22 119.9(4) . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 123.7(4) . . ?
C5 C6 N23 116.2(4) . . ?
C1 C6 N23 120.1(4) . . ?
O8 C7 C1 110.3(4) . . ?
O8 C7 H7A 109.6 . . ?
C1 C7 H7A 109.6 . . ?
O8 C7 H7B 109.6 . . ?
C1 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C10 O8 C7 115.6(4) . . ?
O9 C10 O8 123.3(4) . . ?
O9 C10 C11 126.1(4) . . ?
O8 C10 C11 110.5(4) . . ?
C10 C11 C12 114.6(4) . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 114.8(4) . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 115.1(4) . . ?
C14 C13 H13A 108.5 . . ?
C12 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C12 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C15 C14 C13 128.8(5) . . ?
C15 C14 H14 115.6 . . ?
C13 C14 H14 115.6 . . ?
C14 C15 C16 124.8(5) . . ?
C14 C15 H15 117.6 . . ?
C16 C15 H15 117.6 . . ?
C15 C16 C17 114.1(4) . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 C18 112.7(4) . . ?
C16 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C19 C18 C17 111.5(4) . . ?
C19 C18 H18A 109.3 . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C17 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
O20 C19 O21 122.5(4) . . ?
O20 C19 C18 126.1(5) . . ?
O21 C19 C18 111.4(4) . . ?
C19 O21 C22 115.6(4) . . ?
O21 C22 C4 110.5(4) . . ?
O21 C22 H22A 109.6 . . ?
C4 C22 H22A 109.6 . . ?
O21 C22 H22B 109.6 . . ?
C4 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
O25 N23 O24 123.9(4) . . ?
O25 N23 C6 118.5(4) . . ?
O24 N23 C6 117.6(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 1.395(6) . ?
C1 C6 1.413(7) . ?
C1 C7 1.506(7) . ?
C2 C3 1.387(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(6) . ?
C4 C22 1.495(7) . ?
C5 C6 1.379(7) . ?
C5 H5 0.9500 . ?
C6 N23 1.482(6) . ?
C7 O8 1.440(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O8 C10 1.359(5) . ?
O9 C10 1.188(6) . ?
C10 C11 1.517(7) . ?
C11 C12 1.526(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.521(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.517(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.289(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.489(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.513(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.535(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.497(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O20 1.200(6) . ?
C19 O21 1.359(6) . ?
O21 C22 1.461(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
N23 O25 1.211(5) . ?
N23 O24 1.237(5) . ?
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 -3.7(6) . . . . ?
C7 C1 C2 C3 176.0(4) . . . . ?
C1 C2 C3 C4 0.4(7) . . . . ?
C2 C3 C4 C5 2.7(7) . . . . ?
C2 C3 C4 C22 -177.3(4) . . . . ?
C3 C4 C5 C6 -2.1(6) . . . . ?
C22 C4 C5 C6 177.9(4) . . . . ?
C4 C5 C6 C1 -1.5(7) . . . . ?
C4 C5 C6 N23 177.0(4) . . . . ?
C2 C1 C6 C5 4.3(6) . . . . ?
C7 C1 C6 C5 -175.3(4) . . . . ?
C2 C1 C6 N23 -174.2(4) . . . . ?
C7 C1 C6 N23 6.2(6) . . . . ?
C2 C1 C7 O8 -9.3(6) . . . . ?
C6 C1 C7 O8 170.3(4) . . . . ?
C1 C7 O8 C10 -86.6(5) . . . . ?
C7 O8 C10 O9 -3.1(7) . . . . ?
C7 O8 C10 C11 179.0(4) . . . . ?
O9 C10 C11 C12 22.8(7) . . . . ?
O8 C10 C11 C12 -159.4(4) . . . . ?
C10 C11 C12 C13 83.0(6) . . . . ?
C11 C12 C13 C14 -66.5(6) . . . . ?
C12 C13 C14 C15 -127.2(7) . . . . ?
C13 C14 C15 C16 177.5(5) . . . . ?
C14 C15 C16 C17 115.0(7) . . . . ?
C15 C16 C17 C18 177.7(4) . . . . ?
C16 C17 C18 C19 59.5(6) . . . . ?
C17 C18 C19 O20 -104.4(6) . . . . ?
C17 C18 C19 O21 73.9(5) . . . . ?
O20 C19 O21 C22 4.3(7) . . . . ?
C18 C19 O21 C22 -174.0(4) . . . . ?
C19 O21 C22 C4 68.3(5) . . . . ?
C5 C4 C22 O21 -127.7(4) . . . . ?
C3 C4 C22 O21 52.3(6) . . . . ?
C5 C6 N23 O25 -174.3(4) . . . . ?
C1 C6 N23 O25 4.4(6) . . . . ?
C5 C6 N23 O24 4.1(6) . . . . ?
C1 C6 N23 O24 -177.3(4) . . . . ?
