A Two-Dimensional Polymer Synthesized through Topochemical [2 + 2]-Cycloaddition on the Multigram Scale.
Lange, Ralph Z.; Hofer, Gregor; Weber, Thomas; Schlüter, A Dieter; Journal of the American Chemical Society 139 (2017) 2053–2059; doi:10.1021/jacs.6b11857

data_4125712
_publ_section_title
;
 A Two-Dimensional Polymer Synthesized through Topochemical [2 +
 2]-Cycloaddition on the Multigram Scale.
;
_journal_issue                   5
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2053
_journal_page_last               2059
_journal_paper_doi               10.1021/jacs.6b11857
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety
'C19.18 H22.18 O0.83, 1(B F4), 0.75(H2 O), 0.17(C23 H27 O)'
_chemical_formula_sum            'C23 H28.16 B F4 O1.75'
_chemical_formula_weight         419.42
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-07-20
_audit_creation_method
;
Olex2 1.2
(compiled Feb 16 2016 13:09:46 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   27.0338(5)
_cell_length_b                   27.0338(5)
_cell_length_c                   16.1483(4)
_cell_measurement_reflns_used    83753
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.24
_cell_measurement_theta_min      2.5
_cell_volume                     10220.5(4)
_computing_cell_refinement
'CrysalisPro 1.171.38 (Rigaku Oxford Diffraction, 2015)'
_computing_data_collection
'CrysalisPro 1.171.38 (Rigaku Oxford Diffraction, 2015)'
_computing_data_reduction
'CrysalisPro 1.171.38 (Rigaku Oxford Diffraction, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'Superflip (Palatinus, 2007)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       Transmission
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            83752
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.240
_diffrn_reflns_theta_min         2.149
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       Rhombohedra
_exptl_crystal_F_000             3981
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.906
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         8861
_refine_ls_number_restraints     530
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1622
_refine_ls_R_factor_gt           0.1175
_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/[\s^2^(Fo^2^)+(0.1690P)^2^+28.5040P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3065
_refine_ls_wR_factor_ref         0.3429
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5897
_reflns_number_total             8861
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b11857_si_002.cif
_cod_data_source_block           poly_house_main
_cod_original_cell_volume        10220.4(5)
_cod_database_code               4125712
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Shared sites
{C20A, C2}
3. Restrained distances
 C11B-O1B
 2.72 with sigma of 0.01
 C15B-C12B
 2.77 with sigma of 0.01
 C13B-C14B
 2.77 with sigma of 0.01
 C2B-C3B
 1.48 with sigma of 0.01
 C1B-C2B
 1.4 with sigma of 0.01
 C5B-C1B
 2.97 with sigma of 0.01
 C1B-C4B
 3.68 with sigma of 0.01
 C13B-C14B
 2.72 with sigma of 0.01
 C12B-C15B
 2.72 with sigma of 0.01
 C11B-O1B
 2.72 with sigma of 0.01
 C14B-C15B
 2.35 with sigma of 0.005
 C16B-C12B
 2.6 with sigma of 0.04
 C16B-O1B
 2.36 with sigma of 0.04
 C16B-C11B
 3.8 with sigma of 0.001
 C10B-C13B
 2.44 with sigma of 0.005
 C22B-C21B = C20B-C21B
 1.5 with sigma of 0.02
 C23B-C21B = C22B-C21B = C20B-C21B
 1.5 with sigma of 0.01
 C21A-C20A
 1.5 with sigma of 0.01
 C20A-C22A = C20A-C23A
 1.5 with sigma of 0.01
 C7A-C5A \\sim C5B-C7B \\sim C5A-C3A \\sim C3B-C5B \\sim C4B-C3B \\sim C4A-C3A
\\sim C6A-C4A \\sim C4B-C6B
 \\sim C8B-C6B \\sim C8A-C6A \\sim C8B-C7B \\sim C8A-C7A
 with sigma of 0.004
 O1B-C14B \\sim O1A-C14A \\sim O1A-C15A \\sim O1B-C15B
 with sigma of 0.004
 C15B-C13B \\sim C13A-C15A \\sim C13B-C11B \\sim C13A-C11A \\sim C12B-C11B
\\sim C12A-C11A \\sim C12B-
 C14B \\sim C14A-C12A
 with sigma of 0.004
 C14A-C17A \\sim C14A-C18A \\sim C14A-C19A \\sim C17A-C18A \\sim C17A-C19A
\\sim C18A-C19A
 with sigma of 0.004
 C16A-C14A \\sim C16A-C17A \\sim C16A-C18A \\sim C16A-C19A
 with sigma of 0.002
 C2A-C4A \\sim C2B-C4B
 with sigma of 0.004
 C2B-C5B \\sim C2A-C5A
 with sigma of 0.004
 C19B-C18B \\sim C19B-C17B
 with sigma of 0.02
 C19B-C18B \\sim C18B-C17B \\sim C17B-C19B \\sim C19A-C17A \\sim C17A-C18A
\\sim C18A-C19A
 with sigma of 0.02
 C14A-C16A \\sim C16B-C14B
 with sigma of 0.01
 C16B-C14B \\sim C16B-C19B \\sim C16B-C18B \\sim C16B-C17B
 with sigma of 0.01
 C16B-C18B \\sim C16A-C17A \\sim C19B-C16B \\sim C16A-C19A \\sim C17B-C16B
\\sim C16A-C18A
 with sigma of 0.01
 C10B-C11B \\sim C11A-C10A
 with sigma of 0.02
 C15B-C21B \\sim C16B-C14B \\sim C14A-C16A
 with sigma of 0.01
 C21A-C23A \\sim C23A-C22A \\sim C22A-C21A
 with sigma of 0.01
 C23B-C20B \\sim C20B-C22B \\sim C22B-C23B
 with sigma of 0.01
 C23A-C3 \\sim C21A-C4 \\sim C22A-C1
 with sigma of 0.01
 C1-C23A \\sim C3-C21A \\sim C4-C22A
 with sigma of 0.01
 C23A-C22A \\sim C23A-C21A \\sim C22A-C21A
 with sigma of 0.02
 C1-C4 \\sim C3-C4
 with sigma of 0.02
 C20A-C22A \\sim C21A-C20A \\sim C20A-C23A
 with sigma of 0.01
 C2-C4 \\sim C20A-C21A \\sim C3-C2 \\sim C20A-C23A \\sim C1-C2 \\sim C20A-C22A
 with sigma of 0.01
 C20A-C23A \\sim C20A-C22A \\sim C20A-C21A
 with sigma of 0.01
 C2-C1 \\sim C2-C3 \\sim C2-C4
 with sigma of 0.01
 F3A-F4A \\sim F4A-F1A
 with sigma of 0.004
 B1A-F3A \\sim B1A-F4A \\sim B1A-F2A \\sim B1A-F1A
 with sigma of 0.002
 F1B-F3B \\sim F1B-F2B \\sim F1B-F4B \\sim F3B-F4B \\sim F2B-F4B
 with sigma of 0.004
 B1B-F1B \\sim B1B-F3B \\sim B1B-F2B \\sim B1B-F4B
 with sigma of 0.002
 F3C-F1C \\sim F3C-F2C \\sim F4C-F1C \\sim F4C-F2C \\sim F1C-F2C
 with sigma of 0.02
 B1C-F3C \\sim B1C-F4C \\sim B1C-F1C \\sim B1C-F2C
 with sigma of 0.01
4. Restrained planarity
 C11B, C13B, C12B, C14B, O1B, C15B
 with sigma of 0.005
5. Uiso/Uaniso restraints and constraints
Uanis(C2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(B1B) \\sim Ueq, Uanis(B1A) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uiso(O1B) = Uiso(C7B) = Uiso(C8B) = Uiso(C5B) = Uiso(C9B) = Uiso(C6B) =
Uiso(C3B) = Uiso(C10B) = Uiso(C4B) = Uiso(C2B) = Uiso(C11B) = Uiso(C13B) =
Uiso(C1B) = Uiso(C12B) = Uiso(C15B) = Uiso(C14B) = Uiso(C16B)
Uiso(C18B) = Uiso(C19B) = Uiso(C17B)
Uiso(C22A) = Uiso(C23A) = Uiso(C21A)
Uiso(C20B) = Uiso(C22B) = Uiso(C23B)
Uanis(C20A) = Uanis(C2)
Uiso(C22A) = Uiso(C1) = Uiso(C20B) = Uiso(C23A) = Uiso(C3) = Uiso(C21A) =
Uiso(C4) = Uiso(C23B) = Uiso(C22B)
6. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 1*[Sof(F3A)+Sof(F4A)+Sof(F2A)+Sof(F1A)+Sof(B1A)]+1*[Sof(B1C)+Sof(F3C)+
 Sof(F4C)+Sof(F1C)+Sof(F2C)]+1*[Sof(B1B)+Sof(F1B)+Sof(F3B)+Sof(F2B)+Sof(F4B)]=1
 with esd of 0.0001
 Sof(F3A)=Sof(F4A)=Sof(F2A)=Sof(F1A)=Sof(B1A)=FVAR(1)
 Sof(C7B)=Sof(H7B)=Sof(C10B)=Sof(H10B)=Sof(C9B)=Sof(H9B)=Sof(C8B)=Sof(C4B)=
 Sof(H4BA)=Sof(C5B)=Sof(H5B)=Sof(C6B)=Sof(H6B)=Sof(C3B)=Sof(C11B)=Sof(C13B)=
 Sof(H13B)=Sof(C12B)=Sof(H12B)=Sof(C14B)=Sof(O1B)=Sof(C15B)=Sof(C2B)=Sof(C1B)=
 Sof(H1BA)=Sof(C19B)=Sof(H19D)=Sof(H19E)=Sof(H19F)=Sof(C18B)=Sof(H18D)=
 Sof(H18E)=Sof(H18F)=Sof(C17B)=Sof(H17D)=Sof(H17E)=Sof(H17F)=Sof(C16B)=
 Sof(C21B)=Sof(C20B)=Sof(H20A)=Sof(H20C)=Sof(H20B)=Sof(C22B)=Sof(H22D)=
 Sof(H22E)=Sof(H22F)=Sof(C23B)=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(2)
 Sof(H3C)=0.5*(1-FVAR(3))
 Sof(C20A)=Sof(C23A)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(C22A)=Sof(H22A)=
 Sof(H22B)=Sof(H22C)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C1)=Sof(H1D)=
 Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C4)=Sof(H4B)=Sof(H4C)=
 Sof(H4D)=0.5*FVAR(3)
 Sof(O1A)=Sof(C3A)=Sof(C5A)=Sof(H5A)=Sof(C1A)=Sof(H1A)=Sof(C11A)=Sof(C9A)=
 Sof(H9A)=Sof(C2A)=Sof(C10A)=Sof(H10A)=Sof(C8A)=Sof(C7A)=Sof(H7A)=Sof(C12A)=
 Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(C4A)=Sof(H4A)=Sof(C6A)=Sof(H6A)=
 Sof(C15A)=Sof(C16A)=Sof(C17A)=Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(C18A)=
 Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(C19A)=Sof(H19A)=Sof(H19B)=Sof(H19C)=FVAR(2)
 Sof(O2)=Sof(H2A)=Sof(H2B)=FVAR(3)
 Sof(B1B)=Sof(F1B)=Sof(F3B)=Sof(F2B)=Sof(F4B)=FVAR(4)
 Sof(B1C)=Sof(F3C)=Sof(F4C)=Sof(F1C)=Sof(F2C)=FVAR(5)
8.a Free rotating group:
 O2(H2A,H2B)
8.b Ternary CH refined with riding coordinates:
 C9A(H9A), C10A(H10A), C10B(H10B), C9B(H9B)
8.c Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C1A(H1A), C7A(H7A), C12A(H12A), C13A(H13A), C4A(H4A), C6A(H6A),
 C7B(H7B), C4B(H4BA), C5B(H5B), C6B(H6B), C13B(H13B), C12B(H12B), C1B(H1BA)
8.d Idealised Me refined as rotating group:
 C17A(H17A,H17B,H17C), C18A(H18A,H18B,H18C), C19A(H19A,H19B,H19C), C19B(H19D,
 H19E,H19F), C18B(H18D,H18E,H18F), C17B(H17D,H17E,H17F), C23A(H23A,H23B,H23C),
 C22A(H22A,H22B,H22C), C21A(H21A,H21B,H21C), C1(H1D,H1B,H1C), C3(H3A,H3B,H3C),
 C4(H4B,H4C,H4D), C20B(H20A,H20C,H20B), C22B(H22D,H22E,H22F), C23B(H23D,H23E,
 H23F)
;
_shelx_res_checksum              63253
_shelx_hkl_checksum              26025
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'