#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/41/1554152.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_1554152
loop_
_publ_author_name
'Wang, Zhihan'
'Randazzo, Katelyn'
'Hou, Xiaodong'
'Simpson, Jeffrey'
'Struppe, Jochem'
'Ugrinov, Angel'
'Kastern, Brent'
'Wysocki, Erin'
'Chu, Qianli R.'
_publ_section_title
;
 Stereoregular Two-Dimensional Polymers Constructed by Topochemical
 Polymerization
;
_journal_issue                   9
_journal_name_full               Macromolecules
_journal_page_first              2894
_journal_paper_doi               10.1021/acs.macromol.5b00109
_journal_volume                  48
_journal_year                    2015
_chemical_formula_moiety         'C23 H19 O4'
_chemical_formula_sum            'C23 H19 O4'
_chemical_formula_weight         359.38
_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_date             2014-07-21
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.7260(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5677(4)
_cell_length_b                   9.2109(7)
_cell_length_c                   35.394(3)
_cell_measurement_reflns_used    7453
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      2.303
_cell_volume                     1814.3(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.98
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            21204
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.170
_diffrn_reflns_theta_min         2.285
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0428 before and 0.0393 after correction.
The Ratio of minimum to maximum transmission is 0.9524.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             756
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4019
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0378P)²+0.8524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0934
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3475
_reflns_number_total             4019
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ma5b00109_si_003.cif
_cod_data_source_block           mo_zxw11_0m
_cod_database_code               1554152
_shelxl_version_number           2014-3
_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_max   0.982
_shelx_estimated_absorpt_t_min   0.132
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C22(H22), C23(H23)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O1 O 0.64381(16) 0.13390(10) 0.90613(2) 0.0218(2) Uani 1 1 d .
O2 O 0.00075(15) 0.22929(9) 1.02591(2) 0.0195(2) Uani 1 1 d .
O3 O -0.24546(17) 0.39155(10) 0.99740(3) 0.0256(2) Uani 1 1 d .
O4 O 0.41940(17) 0.21949(11) 0.85685(2) 0.0280(2) Uani 1 1 d .
C1 C 1.2117(2) -0.12041(14) 0.73005(4) 0.0251(3) Uani 1 1 d .
H1 H 1.3033 -0.1734 0.7125 0.030 Uiso 1 1 calc R
C2 C 1.0051(2) -0.04850(14) 0.71793(4) 0.0243(3) Uani 1 1 d .
H2 H 0.9567 -0.0501 0.6920 0.029 Uiso 1 1 calc R
C3 C 0.8686(2) 0.02609(14) 0.74381(3) 0.0215(3) Uani 1 1 d .
H3 H 0.7264 0.0747 0.7353 0.026 Uiso 1 1 calc R
C4 C 0.9372(2) 0.03080(13) 0.78218(3) 0.0190(3) Uani 1 1 d .
C5 C 0.7751(2) 0.10069(13) 0.80859(3) 0.0197(3) Uani 1 1 d .
H5 H 0.6405 0.1503 0.7977 0.024 Uiso 1 1 calc R
C6 C 0.7958(2) 0.10226(14) 0.84625(3) 0.0211(3) Uani 1 1 d .
H6 H 0.9373 0.0656 0.8585 0.025 Uiso 1 1 calc R
C7 C 0.6000(2) 0.16073(13) 0.86893(3) 0.0194(3) Uani 1 1 d .
C8 C 0.4550(2) 0.17281(14) 0.93131(3) 0.0204(3) Uani 1 1 d .
H8A H 0.2963 0.1547 0.9188 0.025 Uiso 1 1 calc R
H8B H 0.4661 0.2773 0.9377 0.025 Uiso 1 1 calc R
C9 C 0.4809(2) 0.08290(12) 0.96684(3) 0.0161(2) Uani 1 1 d .
C10 C 0.3456(2) 0.02506(13) 1.02919(3) 0.0165(2) Uani 1 1 d .
H10 H 0.2395 0.0424 1.0492 0.020 Uiso 1 1 calc R
C11 C 0.3243(2) 0.10834(12) 0.99641(3) 0.0157(2) Uani 1 1 d .
C12 C -0.9872(2) 0.39939(15) 1.15766(4) 0.0244(3) Uani 1 1 d .
H12 H -1.0952 0.3999 1.1779 0.029 Uiso 1 1 calc R
C13 C -1.0047(2) 0.50505(15) 1.12985(4) 0.0243(3) Uani 1 1 d .
H13 H -1.1229 0.5791 1.1312 0.029 Uiso 1 1 calc R
C14 C -0.8481(2) 0.50197(14) 1.09992(4) 0.0215(3) Uani 1 1 d .
H14 H -0.8621 0.5736 1.0807 0.026 Uiso 1 1 calc R
C15 C -0.6705(2) 0.39525(13) 1.09772(3) 0.0177(2) Uani 1 1 d .
C16 C -0.6535(2) 0.29032(14) 1.12636(4) 0.0223(3) Uani 1 1 d .
H16 H -0.5332 0.2173 1.1255 0.027 Uiso 1 1 calc R
C17 C -0.8112(2) 0.29251(15) 1.15589(4) 0.0254(3) Uani 1 1 d .
H17 H -0.7991 0.2205 1.1751 0.031 Uiso 1 1 calc R
C18 C -0.5153(2) 0.39366(13) 1.06492(3) 0.0180(2) Uani 1 1 d .
H18 H -0.5588 0.4572 1.0447 0.022 Uiso 1 1 calc R
C19 C -0.3197(2) 0.31242(13) 1.06050(3) 0.0186(2) Uani 1 1 d .
H19 H -0.2636 0.2507 1.0804 0.022 Uiso 1 1 calc R
C20 C -0.1910(2) 0.31857(13) 1.02482(3) 0.0175(2) Uani 1 1 d .
C21 C 0.1386(2) 0.22639(13) 0.99218(3) 0.0185(2) Uani 1 1 d .
H21A H 0.2180 0.3213 0.9885 0.022 Uiso 1 1 calc R
H21B H 0.0318 0.2070 0.9699 0.022 Uiso 1 1 calc R
C22 C 1.2847(2) -0.11485(15) 0.76797(4) 0.0260(3) Uani 1 1 d .
H22 H 1.4278 -0.1630 0.7762 0.031 Uiso 1 1 calc R
C23 C 1.1501(2) -0.03956(15) 0.79380(4) 0.0230(3) Uani 1 1 d .
H23 H 1.2025 -0.0356 0.8196 0.028 Uiso 1 1 calc R
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'
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
C7 O1 C8 116.20(9) .
C20 O2 C21 115.44(9) .
C2 C1 H1 120.1 .
C2 C1 C22 119.81(12) .
C22 C1 H1 120.1 .
C1 C2 H2 120.1 .
C1 C2 C3 119.90(12) .
C3 C2 H2 120.1 .
C2 C3 H3 119.5 .
C2 C3 C4 121.05(12) .
C4 C3 H3 119.5 .
C3 C4 C5 118.42(11) .
C3 C4 C23 118.28(11) .
C23 C4 C5 123.17(11) .
C4 C5 H5 116.4 .
C6 C5 C4 127.18(12) .
C6 C5 H5 116.4 .
C5 C6 H6 119.9 .
C5 C6 C7 120.29(12) .
C7 C6 H6 119.9 .
O1 C7 C6 110.35(10) .
O4 C7 O1 123.33(11) .
O4 C7 C6 126.26(11) .
O1 C8 H8A 109.9 .
O1 C8 H8B 109.9 .
O1 C8 C9 108.98(9) .
H8A C8 H8B 108.3 .
C9 C8 H8A 109.9 .
C9 C8 H8B 109.9 .
C10 C9 C8 121.69(10) 3_657
C10 C9 C11 119.32(10) 3_657
C11 C9 C8 118.99(10) .
C9 C10 H10 119.4 3_657
C9 C10 C11 121.29(11) 3_657
C11 C10 H10 119.4 .
C9 C11 C21 119.17(10) .
C10 C11 C9 119.38(11) .
C10 C11 C21 121.44(10) .
C13 C12 H12 120.0 .
C13 C12 C17 119.97(12) .
C17 C12 H12 120.0 .
C12 C13 H13 120.2 .
C12 C13 C14 119.58(12) .
C14 C13 H13 120.2 .
C13 C14 H14 119.4 .
C13 C14 C15 121.12(12) .
C15 C14 H14 119.4 .
C14 C15 C16 118.49(11) .
C14 C15 C18 119.02(11) .
C16 C15 C18 122.45(11) .
C15 C16 H16 119.8 .
C17 C16 C15 120.33(12) .
C17 C16 H16 119.8 .
C12 C17 H17 119.8 .
C16 C17 C12 120.49(12) .
C16 C17 H17 119.8 .
C15 C18 H18 116.6 .
C19 C18 C15 126.87(11) .
C19 C18 H18 116.6 .
C18 C19 H19 120.0 .
C18 C19 C20 119.94(11) .
C20 C19 H19 120.0 .
O2 C20 C19 110.96(10) .
O3 C20 O2 122.73(11) .
O3 C20 C19 126.31(11) .
O2 C21 C11 108.24(9) .
O2 C21 H21A 110.0 .
O2 C21 H21B 110.0 .
C11 C21 H21A 110.0 .
C11 C21 H21B 110.0 .
H21A C21 H21B 108.4 .
C1 C22 H22 119.8 .
C23 C22 C1 120.44(12) .
C23 C22 H22 119.8 .
C4 C23 H23 119.8 .
C22 C23 C4 120.49(12) .
C22 C23 H23 119.8 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.3545(14) .
O1 C8 1.4435(14) .
O2 C20 1.3473(14) .
O2 C21 1.4387(13) .
O3 C20 1.2114(15) .
O4 C7 1.2085(15) .
C1 H1 0.9500 .
C1 C2 1.3840(19) .
C1 C22 1.3917(19) .
C2 H2 0.9500 .
C2 C3 1.3895(18) .
C3 H3 0.9500 .
C3 C4 1.4005(17) .
C4 C5 1.4675(17) .
C4 C23 1.4015(18) .
C5 H5 0.9500 .
C5 C6 1.3347(17) .
C6 H6 0.9500 .
C6 C7 1.4753(17) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C8 C9 1.5090(16) .
C9 C10 1.3905(16) 3_657
C9 C11 1.4020(16) .
C10 C9 1.3904(16) 3_657
C10 H10 0.9500 .
C10 C11 1.3930(16) .
C11 C21 1.5051(16) .
C12 H12 0.9500 .
C12 C13 1.3855(19) .
C12 C17 1.3918(19) .
C13 H13 0.9500 .
C13 C14 1.3928(18) .
C14 H14 0.9500 .
C14 C15 1.3982(17) .
C15 C16 1.4017(17) .
C15 C18 1.4678(16) .
C16 H16 0.9500 .
C16 C17 1.3855(18) .
C17 H17 0.9500 .
C18 H18 0.9500 .
C18 C19 1.3345(17) .
C19 H19 0.9500 .
C19 C20 1.4719(16) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 H22 0.9500 .
C22 C23 1.3854(18) .
C23 H23 0.9500 .
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_4
O1 C8 C9 C10 -4.21(16) . 3_657
O1 C8 C9 C11 176.36(10) . .
C1 C2 C3 C4 0.4(2) . .
C1 C22 C23 C4 0.7(2) . .
C2 C1 C22 C23 0.9(2) . .
C2 C3 C4 C5 -174.86(12) . .
C2 C3 C4 C23 1.15(19) . .
C3 C4 C5 C6 172.20(13) . .
C3 C4 C23 C22 -1.69(19) . .
C4 C5 C6 C7 -171.76(12) . .
C5 C4 C23 C22 174.12(12) . .
C5 C6 C7 O1 171.68(12) . .
C5 C6 C7 O4 -5.6(2) . .
C7 O1 C8 C9 156.22(10) . .
C8 O1 C7 O4 3.15(18) . .
C8 O1 C7 C6 -174.19(10) . .
C8 C9 C11 C10 179.48(11) . .
C8 C9 C11 C21 -1.22(17) . .
C9 C10 C11 C9 0.0(2) 3_657 .
C9 C10 C11 C21 -179.32(11) 3_657 .
C9 C11 C21 O2 179.42(10) . .
C10 C9 C11 C10 0.03(19) 3_657 .
C10 C9 C11 C21 179.34(11) 3_657 .
C10 C11 C21 O2 -1.29(16) . .
C12 C13 C14 C15 -1.0(2) . .
C13 C12 C17 C16 -0.3(2) . .
C13 C14 C15 C16 0.22(19) . .
C13 C14 C15 C18 177.87(12) . .
C14 C15 C16 C17 0.52(19) . .
C14 C15 C18 C19 170.92(12) . .
C15 C16 C17 C12 -0.5(2) . .
C15 C18 C19 C20 176.81(11) . .
C16 C15 C18 C19 -11.5(2) . .
C17 C12 C13 C14 1.1(2) . .
C18 C15 C16 C17 -177.04(12) . .
C18 C19 C20 O2 179.93(11) . .
C18 C19 C20 O3 -0.7(2) . .
C20 O2 C21 C11 -172.85(10) . .
C21 O2 C20 O3 0.19(17) . .
C21 O2 C20 C19 179.59(10) . .
C22 C1 C2 C3 -1.5(2) . .
C23 C4 C5 C6 -3.6(2) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132562515
