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#$Date: 2023-06-05 08:01:54 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284344 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/88/1568882.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_1568882
loop_
_publ_author_name
'Young, Taylor B.'
'Guppy, Owaen G.'
'Draper, Alysia J.'
'Whitington, Joshua M.'
'Kariuki, Benson M.'
'Paul, Alison'
'Eaton, Mark'
'Pope, Simon J. A.'
'Ward, Benjamin D.'
_publ_section_title
;
 Chemically recyclable fluorescent polyesters via the ring-opening
 copolymerization of epoxides and anhydrides
;
_journal_issue                   20
_journal_name_full               'Polymer Chemistry'
_journal_page_first              2478
_journal_page_last               2484
_journal_paper_doi               10.1039/D3PY00209H
_journal_volume                  14
_journal_year                    2023
_chemical_formula_sum            'C17 H13 N O3'
_chemical_formula_weight         279.28
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-07-07 deposited with the CCDC.	2023-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   29.6286(6)
_cell_length_b                   29.6286(6)
_cell_length_c                   7.6747(3)
_cell_measurement_reflns_used    6933
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.8330
_cell_measurement_theta_min      2.3930
_cell_volume                     5834.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            33544
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.381
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_description       '(cut) block'
_exptl_crystal_F_000             2628
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, petroleum ether'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     103
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0668
_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)+(0.1350P)²+3.7120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2022
_refine_ls_wR_factor_ref         0.2181
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2303
_reflns_number_total             2976
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3py00209h2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 1568881--1568883.cif.'
_cod_database_code               1568882
_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   0.971
_shelx_estimated_absorpt_t_max   0.998
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
O1 O 0.5989(3) 0.3052(3) 0.6394(11) 0.157(3) Uani 0.452(8) 1 d D U P A 1
C1 C 0.5662(5) 0.2550(6) 0.545(2) 0.131(4) Uani 0.452(8) 1 d D U P A 1
H1A H 0.584476 0.243203 0.464912 0.157 Uiso 0.452(8) 1 calc R U P A 1
H1B H 0.537147 0.226520 0.610178 0.157 Uiso 0.452(8) 1 calc R U P A 1
C2 C 0.5605(6) 0.2867(6) 0.499(2) 0.141(4) Uani 0.452(8) 1 d D U P A 1
H2 H 0.574625 0.300542 0.380645 0.170 Uiso 0.452(8) 1 calc R U P A 1
C3 C 0.5178(7) 0.3035(8) 0.579(3) 0.137(5) Uani 0.452(8) 1 d . U P A 1
H3A H 0.519166 0.305101 0.707912 0.164 Uiso 0.452(8) 1 calc R U P A 1
H3B H 0.525229 0.337764 0.533021 0.164 Uiso 0.452(8) 1 calc R U P A 1
O1A O 0.5542(2) 0.2553(3) 0.6532(9) 0.142(3) Uani 0.548(8) 1 d D U P A 2
C1A C 0.5581(3) 0.2613(4) 0.4615(9) 0.096(2) Uani 0.548(8) 1 d D U P A 2
H1AA H 0.591466 0.269472 0.405501 0.115 Uiso 0.548(8) 1 calc R U P A 2
H1AB H 0.526497 0.239516 0.391340 0.115 Uiso 0.548(8) 1 calc R U P A 2
C2A C 0.5579(2) 0.3000(3) 0.5770(9) 0.0855(18) Uani 0.548(8) 1 d D U P A 2
H2A H 0.592437 0.332377 0.591655 0.103 Uiso 0.548(8) 1 calc R U P A 2
C3A C 0.5135(2) 0.3084(4) 0.5655(11) 0.0660(17) Uani 0.548(8) 1 d . U P A 2
H3A1 H 0.508392 0.320844 0.679427 0.079 Uiso 0.548(8) 1 calc R U P A 2
H3A2 H 0.520994 0.335750 0.477843 0.079 Uiso 0.548(8) 1 calc R U P A 2
O2 O 0.41766(6) 0.16839(6) 0.36694(19) 0.0582(4) Uani 1 1 d . . . . .
O3 O 0.23195(6) 0.15655(5) 0.46914(19) 0.0553(4) Uani 1 1 d . . . . .
N1 N 0.46589(7) 0.26105(8) 0.5173(3) 0.0616(5) Uani 1 1 d D . . . .
H1N H 0.4677(11) 0.2378(9) 0.450(3) 0.074 Uiso 1 1 d D U . . .
C4 C 0.41833(8) 0.25578(8) 0.5364(2) 0.0491(5) Uani 1 1 d . . . . .
C5 C 0.41213(8) 0.29577(7) 0.6153(2) 0.0514(5) Uani 1 1 d . . . . .
H5 H 0.442052 0.326869 0.653062 0.062 Uiso 1 1 calc R U . . .
C6 C 0.36382(8) 0.29021(7) 0.6376(2) 0.0505(5) Uani 1 1 d . . . . .
H6 H 0.360775 0.317484 0.691046 0.061 Uiso 1 1 calc R U . . .
C7 C 0.31919(8) 0.24548(7) 0.5837(2) 0.0458(4) Uani 1 1 d . . . . .
H7 H 0.285843 0.241976 0.601355 0.055 Uiso 1 1 calc R U . . .
C8 C 0.32367(7) 0.20594(7) 0.5038(2) 0.0413(4) Uani 1 1 d . . . . .
C9 C 0.27436(7) 0.15973(7) 0.4458(2) 0.0442(4) Uani 1 1 d . . . . .
C10 C 0.27811(8) 0.11754(7) 0.3547(2) 0.0456(4) Uani 1 1 d . . . . .
C11 C 0.23275(9) 0.07391(7) 0.2937(3) 0.0562(5) Uani 1 1 d . . . . .
H11 H 0.199734 0.071195 0.311106 0.067 Uiso 1 1 calc R U . . .
C12 C 0.23636(11) 0.03463(8) 0.2075(3) 0.0630(6) Uani 1 1 d . . . . .
H12 H 0.205712 0.004798 0.166440 0.076 Uiso 1 1 calc R U . . .
C13 C 0.28438(11) 0.03889(8) 0.1814(3) 0.0640(7) Uani 1 1 d . . . . .
H13 H 0.286528 0.011937 0.121693 0.077 Uiso 1 1 calc R U . . .
C14 C 0.32934(10) 0.08170(8) 0.2408(2) 0.0564(6) Uani 1 1 d . . . . .
H14 H 0.362154 0.084104 0.221730 0.068 Uiso 1 1 calc R U . . .
C15 C 0.32667(8) 0.12162(7) 0.3293(2) 0.0463(5) Uani 1 1 d . . . . .
C16 C 0.37565(8) 0.16736(7) 0.3914(2) 0.0459(4) Uani 1 1 d . . . . .
C17 C 0.37276(7) 0.20975(7) 0.4785(2) 0.0431(4) 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 O1 C1 43.3(8) . . ?
C2 C1 O1 66.4(9) . . ?
C1 C2 O1 70.3(9) . . ?
C1 C2 C3 127(2) . . ?
O1 C2 C3 100.4(14) . . ?
N1 C3 C2 104.2(13) . . ?
C2A O1A C1A 60.5(5) . . ?
C2A C1A O1A 57.0(4) . . ?
O1A C2A C1A 62.5(5) . . ?
O1A C2A C3A 122.4(7) . . ?
C1A C2A C3A 117.3(6) . . ?
N1 C3A C2A 111.9(7) . . ?
C4 N1 C3A 122.6(4) . . ?
C4 N1 C3 129.8(8) . . ?
N1 C4 C5 120.91(18) . . ?
N1 C4 C17 120.81(19) . . ?
C5 C4 C17 118.28(17) . . ?
C6 C5 C4 121.11(17) . . ?
C5 C6 C7 121.22(18) . . ?
C8 C7 C6 119.39(18) . . ?
C7 C8 C17 121.49(17) . . ?
C7 C8 C9 116.45(16) . . ?
C17 C8 C9 122.06(15) . . ?
O3 C9 C10 120.65(17) . . ?
O3 C9 C8 121.70(16) . . ?
C10 C9 C8 117.64(16) . . ?
C15 C10 C11 120.36(18) . . ?
C15 C10 C9 120.06(17) . . ?
C11 C10 C9 119.58(18) . . ?
C12 C11 C10 119.5(2) . . ?
C13 C12 C11 120.1(2) . . ?
C12 C13 C14 120.94(19) . . ?
C13 C14 C15 120.1(2) . . ?
C10 C15 C14 119.07(19) . . ?
C10 C15 C16 121.94(15) . . ?
C14 C15 C16 118.99(18) . . ?
O2 C16 C17 122.36(18) . . ?
O2 C16 C15 118.92(17) . . ?
C17 C16 C15 118.73(16) . . ?
C8 C17 C4 118.49(16) . . ?
C8 C17 C16 119.55(16) . . ?
C4 C17 C16 121.94(17) . . ?
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
O1 C2 1.458(12) . ?
O1 C1 1.497(12) . ?
C1 C2 1.090(19) . ?
C2 C3 1.69(3) . ?
C3 N1 1.496(18) . ?
O1A C2A 1.399(9) . ?
O1A C1A 1.479(9) . ?
C1A C2A 1.451(10) . ?
C2A C3A 1.459(10) . ?
C3A N1 1.454(7) . ?
O2 C16 1.244(2) . ?
O3 C9 1.225(2) . ?
N1 C4 1.346(3) . ?
C4 C5 1.422(3) . ?
C4 C17 1.428(3) . ?
C5 C6 1.367(3) . ?
C6 C7 1.387(3) . ?
C7 C8 1.386(2) . ?
C8 C17 1.415(2) . ?
C8 C9 1.485(3) . ?
C9 C10 1.484(2) . ?
C10 C15 1.396(3) . ?
C10 C11 1.400(3) . ?
C11 C12 1.388(3) . ?
C12 C13 1.379(4) . ?
C13 C14 1.379(3) . ?
C14 C15 1.400(3) . ?
C15 C16 1.484(3) . ?
C16 C17 1.463(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O2 0.886(17) 1.94(2) 2.643(3) 135(2) . yes
