Gram-scale synthesis of two-dimensional polymer crystals and their structure analysis by X-ray diffraction
Max J. Kory; Michael Worle; Thomas Weber; Payam Payamyar; Stan W. van de Poll; Julia Dshemuchadse; Nils Trapp; Dieter Schluter; Nature Chemistry 6 (2014) 779–784; doi:10.1038/nchem.2007

data_1551373
_publ_section_title
;
 Gram-scale synthesis of two-dimensional polymer crystals and their
 structure analysis by X-ray diffraction
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              779
_journal_page_last               784
_journal_paper_doi               10.1038/nchem.2007
_journal_volume                  6
_journal_year                    2014
_chemical_formula_moiety         '3(C48 H24 N6 O6), 4(C6 H4 N2)'
_chemical_formula_sum            'C168 H88 N26 O18'
_chemical_formula_weight         2758.64
_chemical_name_systematic
1,5,10-(1,8)trianthracena-2,4,5,8,9,11-hexaoxa-3,7(1,3,5)ditriazinabicyclo[3.3.3]undecaphane
_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_Hall           'R 3'
_space_group_name_H-M_alt        'R 3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   19.3322(8)
_cell_length_b                   19.3322(8)
_cell_length_c                   28.9191(13)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.091
_cell_measurement_theta_min      2.533
_cell_volume                     9360.0(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon 100 area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'focusing graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            55177
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.156
_diffrn_reflns_theta_min         2.533
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.9372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0515 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.9657.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      .
_exptl_crystal_description       prism
_exptl_crystal_F_000             4266
_exptl_crystal_preparation       'Monomer crystal without irradiation'
_exptl_crystal_recrystallization_method 'crystallized from o-cyanopyridin'
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 3720 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     591
_refine_ls_number_reflns         9182
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0563
_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/[\s^2^(Fo^2^)+(0.0940P)^2^+13.9153P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1568
_reflns_Friedel_coverage         0.994
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                8145
_reflns_number_total             9182
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            nchem.2007-s2.cif
_cod_data_source_block           1
_cod_original_cell_volume        9360.0(9)
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               1551373
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{N3, N3B}
{C17, C17B}
{C18, C18B}
{N19, C19B}
{C20, C20B}
{C21, C21B}
{C22, C22B}
{C23, N23B}
{N3A, N3C}
{C17A, C17C}
{C18A, C18C}
{N19A, C19C}
{C20A, C20C}
{C21A, C21C}
{C22A, C22C}
{C23A, N23C}
{N4, N4A}
{C24, C24A}
{C25, C25A}
{N26, C26A}
{C27, C27A}
{C28, C28A}
{C29, C29A}
{C30, N30A}
3. Uiso/Uaniso restraints and constraints
Uiso(N3) = Uiso(C17) = Uiso(C18) = Uiso(N19) = Uiso(C20) = Uiso(C21) =
Uiso(C22) = Uiso(C23) = Uiso(N3B) = Uiso(C17B) = Uiso(C18B) = Uiso(C19B) =
Uiso(C20B) = Uiso(C21B) = Uiso(C22B) = Uiso(N23B) = Uiso(N3A) = Uiso(C17A) =
Uiso(C18A) = Uiso(N19A) = Uiso(C20A) = Uiso(C21A) = Uiso(C22A) = Uiso(C23A) =
Uiso(N3C) = Uiso(C17C) = Uiso(C18C) = Uiso(C19C) = Uiso(C20C) = Uiso(C21C) =
Uiso(C22C) = Uiso(N23C)
Uiso(N4) = Uiso(N4A) = Uiso(C24) = Uiso(C24A) = Uiso(C25) = Uiso(C25A) =
Uiso(N26) = Uiso(C26A) = Uiso(C27) = Uiso(C27A) = Uiso(C28) = Uiso(C28A) =
Uiso(C29) = Uiso(C29A) = Uiso(C30) = Uiso(N30A)
4. Others
 Fixed Sof: N3A(0.16667) C17A(0.16667) C23A(0.16667) H23A(0.16667)
 C18A(0.16667) N19A(0.16667) C20A(0.16667) H20A(0.16667) C21A(0.16667)
 H21A(0.16667) C22A(0.16667) H22A(0.16667) N3(0.33333) C17(0.33333)
 C18(0.33333) N19(0.33333) C20(0.33333) H20(0.33333) C21(0.33333) H21(0.33333)
 C22(0.33333) H22(0.33333) C23(0.33333) H23(0.33333) C24(0.16667) C25(0.16667)
 N26(0.16667) C27(0.16667) H27(0.16667) C28(0.16667) H28(0.16667) C29(0.16667)
 H29(0.16667) C30(0.16667) H30(0.16667) N4(0.16667) C24A(0.16667) C25A(0.16667)
 C26A(0.16667) H26A(0.16667) C27A(0.16667) H27A(0.16667) C28A(0.16667)
 H28A(0.16667) C29A(0.16667) H29A(0.16667) N30A(0.16667) N4A(0.16667)
 N3B(0.33333) C17B(0.33333) C18B(0.33333) C19B(0.33333) H19B(0.33333)
 C20B(0.33333) H20B(0.33333) C21B(0.33333) H21B(0.33333) C22B(0.33333)
 H22B(0.33333) N23B(0.33333) N3C(0.16667) C17C(0.16667) N23C(0.16667)
 C18C(0.16667) C19C(0.16667) H19C(0.16667) C20C(0.16667) H20C(0.16667)
 C21C(0.16667) H21C(0.16667) C22C(0.16667) H22C(0.16667)
5.a Free rotating group:
 C24(C25,N26,C27,C28,C29,C30,N4), C24A(C25A,C26A,C27A,C28A,C29A,N30A,N4A)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C8(H8), C9(H9), C10(H10), C13(H13), C2A(H2A),
 C3A(H3A), C4A(H4A), C6A(H6A), C8A(H8A), C9A(H9A), C10A(H10A), C13A(H13A),
 C2B(H2B), C3B(H3B), C4B(H4B), C6B(H6B), C8B(H8B), C9B(H9B), C10B(H10B),
 C13B(H13B), C23A(H23A), C20A(H20A), C21A(H21A), C22A(H22A), C20(H20), C21(H21),
  C22(H22), C23(H23), C27(H27), C28(H28), C29(H29), C30(H30), C26A(H26A),
 C27A(H27A), C28A(H28A), C29A(H29A), C19B(H19B), C20B(H20B), C21B(H21B),
 C22B(H22B), C19C(H19C), C20C(H20C), C21C(H21C), C22C(H22C)
5.c Fitted hexagon refined as free rotating group:
 C23A(C18A,N19A,C20A,C21A,C22A), N23C(C18C,C19C,C20C,C21C,C22C)
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_shelx_res_checksum              87854
_shelx_hkl_checksum              30424