#------------------------------------------------------------------------------
#$Date: 2023-01-06 12:06:30 +0200 (Fri, 06 Jan 2023) $
#$Revision: 280224 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/76/1567627.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_1567627
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 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 91.5968(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8712(4)
_cell_length_b                   16.4752(7)
_cell_length_c                   11.7570(5)
_cell_measurement_reflns_used    8543
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.87
_cell_volume                     1524.05(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 0.983
_diffrn_measured_fraction_theta_max 0.985
_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  0.0547
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.983
_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       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20523
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.869
_diffrn_source                   'I\^I1/4S 3.0 Microfocus'
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.096
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.201
_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     245
_refine_ls_number_reflns         3447
_refine_ls_number_restraints     148
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0369
_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)+(0.0317P)²+0.4916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0932
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2852
_reflns_number_total             3447
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2py00684g2.cif
_cod_data_source_block           027_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/n'
_cod_database_code               1567627
_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   0.969
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.41523(16) 0.55267(7) 0.64524(12) 0.0309(3) Uani 1 1 d . . . . .
H1A H 0.381964 0.543439 0.724794 0.037 Uiso 1 1 calc R U . . .
H1B H 0.339511 0.519946 0.594632 0.037 Uiso 1 1 calc R U . . .
O2 O 0.59135(11) 0.52796(5) 0.63145(7) 0.0299(2) Uani 1 1 d . . . . .
O3 O 0.66097(12) 0.57846(6) 0.80421(8) 0.0357(2) Uani 1 1 d . . . . .
C4 C 0.70340(16) 0.54994(7) 0.71498(10) 0.0267(3) Uani 1 1 d . . . . .
C5 C 0.88193(17) 0.53591(8) 0.67928(11) 0.0323(3) Uani 1 1 d D . . . .
H5A H 0.892042 0.480420 0.647863 0.039 Uiso 1 1 calc R U . A 1
H5B H 0.960157 0.540279 0.746408 0.039 Uiso 1 1 calc R U . A 1
C6 C 0.9330(4) 0.59829(10) 0.58883(17) 0.0307(4) Uani 0.923(4) 1 d . U P B 1
H6A H 1.041152 0.581064 0.555230 0.037 Uiso 0.923(4) 1 calc R U P B 1
H6B H 0.844792 0.599519 0.527164 0.037 Uiso 0.923(4) 1 calc R U P B 1
C7 C 0.9542(2) 0.68215(9) 0.63751(12) 0.0291(4) Uani 0.923(4) 1 d . U P B 1
H7 H 1.039147 0.689779 0.695479 0.035 Uiso 0.923(4) 1 calc R U P B 1
C8 C 0.8630(3) 0.74619(10) 0.60552(13) 0.0303(4) Uani 0.923(4) 1 d . U P B 1
H8 H 0.773749 0.738115 0.550658 0.036 Uiso 0.923(4) 1 calc R U P B 1
C9 C 0.8914(4) 0.83122(15) 0.6503(2) 0.0348(5) Uani 0.923(4) 1 d . U P B 1
H9A H 1.004427 0.833879 0.689265 0.042 Uiso 0.923(4) 1 calc R U P B 1
H9B H 0.804780 0.843266 0.707413 0.042 Uiso 0.923(4) 1 calc R U P B 1
C6B C 0.924(5) 0.6128(10) 0.608(2) 0.033(3) Uani 0.077(4) 1 d D U P B 2
H6BA H 1.049079 0.614036 0.604442 0.039 Uiso 0.077(4) 1 calc R U P B 2
H6BB H 0.880883 0.600887 0.529980 0.039 Uiso 0.077(4) 1 calc R U P B 2
C7B C 0.870(3) 0.7012(11) 0.6317(16) 0.030(2) Uani 0.077(4) 1 d D U P B 2
H7B H 0.770306 0.707727 0.674275 0.036 Uiso 0.077(4) 1 calc R U P B 2
C8B C 0.938(3) 0.7618(13) 0.6034(17) 0.034(2) Uani 0.077(4) 1 d D U P B 2
H8B H 1.027884 0.762946 0.551500 0.040 Uiso 0.077(4) 1 calc R U P B 2
C9B C 0.865(6) 0.8387(13) 0.6586(19) 0.031(3) Uani 0.077(4) 1 d D U P B 2
H9BA H 0.934742 0.856547 0.725477 0.037 Uiso 0.077(4) 1 calc R U P B 2
H9BB H 0.745598 0.831559 0.680357 0.037 Uiso 0.077(4) 1 calc R U P B 2
C10 C 0.88198(18) 0.89665(8) 0.55649(12) 0.0367(3) Uani 1 1 d D . . . .
H10A H 0.904726 0.950573 0.590803 0.044 Uiso 1 1 calc R U . B 1
H10B H 0.970736 0.885926 0.500386 0.044 Uiso 1 1 calc R U . B 1
C11 C 0.71098(18) 0.89756(7) 0.49688(11) 0.0321(3) Uani 1 1 d . . . . .
O12 O 0.68344(15) 0.88174(8) 0.39850(9) 0.0533(3) Uani 1 1 d . . . . .
O13 O 0.58662(11) 0.91684(5) 0.56921(7) 0.0292(2) Uani 1 1 d . . . . .
C14 C 0.41387(17) 0.89612(8) 0.53173(11) 0.0318(3) Uani 1 1 d . . . . .
H14A H 0.399046 0.904491 0.448660 0.038 Uiso 1 1 calc R U . . .
H14B H 0.330635 0.930494 0.571016 0.038 Uiso 1 1 calc R U . . .
C15 C 0.38826(15) 0.80802(7) 0.56129(10) 0.0253(2) Uani 1 1 d . . . . .
C16 C 0.37481(17) 0.74905(8) 0.47702(11) 0.0314(3) Uani 1 1 d . . . . .
H16 H 0.362867 0.765168 0.399629 0.038 Uiso 1 1 calc R U . . .
C17 C 0.37853(16) 0.66690(8) 0.50393(11) 0.0301(3) Uani 1 1 d . . . . .
H17 H 0.368063 0.627768 0.444797 0.036 Uiso 1 1 calc R U . . .
C18 C 0.39730(14) 0.64131(7) 0.61593(10) 0.0252(3) Uani 1 1 d . . . . .
C19 C 0.40774(14) 0.69914(7) 0.70212(10) 0.0236(2) Uani 1 1 d . . . . .
H19 H 0.418971 0.683036 0.779554 0.028 Uiso 1 1 calc R U . . .
C20 C 0.40150(14) 0.78028(7) 0.67318(10) 0.0222(2) Uani 1 1 d . . . . .
N21 N 0.41417(13) 0.83802(6) 0.76867(9) 0.0269(2) Uani 1 1 d . . . . .
O22 O 0.31178(13) 0.89409(6) 0.77136(9) 0.0408(3) Uani 1 1 d . . . . .
O23 O 0.52548(13) 0.82633(6) 0.84143(8) 0.0392(2) 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
O2 C1 C18 109.18(9) . . ?
O2 C1 H1A 109.8 . . ?
C18 C1 H1A 109.8 . . ?
O2 C1 H1B 109.8 . . ?
C18 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
C4 O2 C1 116.60(9) . . ?
O3 C4 O2 123.10(12) . . ?
O3 C4 C5 126.15(12) . . ?
O2 C4 C5 110.73(10) . . ?
C4 C5 C6 110.85(14) . . ?
C4 C5 C6B 103.8(13) . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C7 C6 C5 112.26(14) . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 124.81(19) . . ?
C8 C7 H7 117.6 . . ?
C6 C7 H7 117.6 . . ?
C7 C8 C9 124.5(2) . . ?
C7 C8 H8 117.8 . . ?
C9 C8 H8 117.8 . . ?
C8 C9 C10 113.2(2) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C7B C6B C5 127.5(17) . . ?
C7B C6B H6BA 105.4 . . ?
C5 C6B H6BA 105.4 . . ?
C7B C6B H6BB 105.4 . . ?
C5 C6B H6BB 105.4 . . ?
H6BA C6B H6BB 106.0 . . ?
C8B C7B C6B 128(2) . . ?
C8B C7B H7B 115.8 . . ?
C6B C7B H7B 115.8 . . ?
C7B C8B C9B 114(3) . . ?
C7B C8B H8B 123.1 . . ?
C9B C8B H8B 123.1 . . ?
C8B C9B C10 98.1(13) . . ?
C8B C9B H9BA 112.1 . . ?
C10 C9B H9BA 112.1 . . ?
C8B C9B H9BB 112.1 . . ?
C10 C9B H9BB 112.1 . . ?
H9BA C9B H9BB 109.8 . . ?
C11 C10 C9B 106.0(19) . . ?
C11 C10 C9 111.45(17) . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
O12 C11 O13 122.88(13) . . ?
O12 C11 C10 125.73(13) . . ?
O13 C11 C10 111.37(11) . . ?
C11 O13 C14 116.12(10) . . ?
O13 C14 C15 106.57(10) . . ?
O13 C14 H14A 110.4 . . ?
C15 C14 H14A 110.4 . . ?
O13 C14 H14B 110.4 . . ?
C15 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
C16 C15 C20 116.48(11) . . ?
C16 C15 C14 121.12(11) . . ?
C20 C15 C14 121.77(11) . . ?
C15 C16 C17 121.18(12) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 120.87(11) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.07(11) . . ?
C17 C18 C1 121.26(11) . . ?
C19 C18 C1 119.60(11) . . ?
C20 C19 C18 118.86(11) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C19 C20 C15 123.48(10) . . ?
C19 C20 N21 115.89(10) . . ?
C15 C20 N21 120.62(10) . . ?
O23 N21 O22 123.98(10) . . ?
O23 N21 C20 117.62(10) . . ?
O22 N21 C20 118.39(10) . . ?
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 O2 1.4581(15) . ?
C1 C18 1.5062(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
O2 C4 1.3510(15) . ?
O3 C4 1.2052(15) . ?
C4 C5 1.4958(18) . ?
C5 C6 1.540(2) . ?
C5 C6B 1.558(10) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.503(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.324(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.511(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.543(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C6B C7B 1.542(10) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C7B C8B 1.18(3) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.539(10) . ?
C8B H8B 0.9500 . ?
C9B C10 1.542(10) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C10 C11 1.500(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O12 1.1995(17) . ?
C11 O13 1.3522(15) . ?
O13 C14 1.4582(16) . ?
C14 C15 1.5074(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.3896(17) . ?
C15 C20 1.3938(16) . ?
C16 C17 1.3901(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.3867(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.3917(16) . ?
C19 C20 1.3799(16) . ?
C19 H19 0.9500 . ?
C20 N21 1.4728(14) . ?
N21 O23 1.2226(14) . ?
N21 O22 1.2269(13) . ?
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
C18 C1 O2 C4 77.30(13) . . . . ?
C1 O2 C4 O3 10.05(16) . . . . ?
C1 O2 C4 C5 -168.47(10) . . . . ?
O3 C4 C5 C6 -106.54(16) . . . . ?
O2 C4 C5 C6 71.92(15) . . . . ?
O3 C4 C5 C6B -95.6(14) . . . . ?
O2 C4 C5 C6B 82.8(14) . . . . ?
C4 C5 C6 C7 70.5(2) . . . . ?
C5 C6 C7 C8 -118.4(2) . . . . ?
C6 C7 C8 C9 -176.53(18) . . . . ?
C7 C8 C9 C10 136.7(2) . . . . ?
C4 C5 C6B C7B 38(4) . . . . ?
C5 C6B C7B C8B 155(3) . . . . ?
C6B C7B C8B C9B -170(3) . . . . ?
C7B C8B C9B C10 -144(2) . . . . ?
C8B C9B C10 C11 97(2) . . . . ?
C8 C9 C10 C11 60.6(2) . . . . ?
C9B C10 C11 O12 -124.2(9) . . . . ?
C9 C10 C11 O12 -115.74(17) . . . . ?
C9B C10 C11 O13 54.3(9) . . . . ?
C9 C10 C11 O13 62.70(15) . . . . ?
O12 C11 O13 C14 16.44(17) . . . . ?
C10 C11 O13 C14 -162.04(10) . . . . ?
C11 O13 C14 C15 83.12(12) . . . . ?
O13 C14 C15 C16 -110.22(13) . . . . ?
O13 C14 C15 C20 60.34(14) . . . . ?
C20 C15 C16 C17 -1.44(18) . . . . ?
C14 C15 C16 C17 169.59(12) . . . . ?
C15 C16 C17 C18 -0.6(2) . . . . ?
C16 C17 C18 C19 1.78(18) . . . . ?
C16 C17 C18 C1 -175.15(11) . . . . ?
O2 C1 C18 C17 81.83(14) . . . . ?
O2 C1 C18 C19 -95.08(13) . . . . ?
C17 C18 C19 C20 -0.92(17) . . . . ?
C1 C18 C19 C20 176.07(10) . . . . ?
C18 C19 C20 C15 -1.20(17) . . . . ?
C18 C19 C20 N21 -179.68(10) . . . . ?
C16 C15 C20 C19 2.36(17) . . . . ?
C14 C15 C20 C19 -168.62(11) . . . . ?
C16 C15 C20 N21 -179.23(11) . . . . ?
C14 C15 C20 N21 9.80(17) . . . . ?
C19 C20 N21 O23 46.63(15) . . . . ?
C15 C20 N21 O23 -131.90(12) . . . . ?
C19 C20 N21 O22 -132.46(11) . . . . ?
C15 C20 N21 O22 49.01(15) . . . . ?
