A Wavy Two-Dimensional Covalent Organic Framework from Core-Twisted Polycyclic Aromatic Hydrocarbons.
Martínez-Abadía, Marta; Stoppiello, Craig T.; Strutynski, Karol; Lerma-Berlanga, Belén; Martí-Gastaldo, Carlos; Saeki, Akinori; Melle-Franco, Manuel; Khlobystov, Andrei N.; Mateo-Alonso, Aurelio; Journal of the American Chemical Society 141 (2019) 14403–14410; doi:10.1021/jacs.9b07383

data_4128816
_publ_section_title
;
 A Wavy Two-Dimensional Covalent Organic Framework from Core-Twisted
 Polycyclic Aromatic Hydrocarbons.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14403
_journal_page_last               14410
_journal_paper_doi               10.1021/jacs.9b07383
_journal_volume                  141
_journal_year                    2019
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C48 H24 O6'
_chemical_formula_sum            'C48 H24 O6'
_chemical_formula_weight         696.67
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-06-08T14:09:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                67.779(4)
_cell_angle_beta                 76.113(4)
_cell_angle_gamma                79.561(3)
_cell_formula_units_Z            2
_cell_length_a                   13.0079(6)
_cell_length_b                   14.5518(5)
_cell_length_c                   18.7581(7)
_cell_measurement_reflns_used    7189
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.747
_cell_measurement_theta_min      3.935
_cell_measurement_wavelength     1.54184
_cell_volume                     3174.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -123.00 -93.00   1.00    5.00    --  -41.33 -99.00-180.00   30
  2  \w   -122.00 -82.00   1.00    5.00    --  -41.33 -99.00 -60.00   40
  3  \w   -117.00 -80.00   1.00    5.00    --  -41.33 -99.00 -30.00   37
  4  \w    -67.00  25.00   1.00    5.00    --  -41.33  38.00  60.00   92
  5  \w    -65.00 -27.00   1.00    5.00    --  -41.33  38.00  30.00   38
  6  \w    -17.00  83.00   1.00    5.00    --   41.33 -99.00-150.00  100
  7  \w   -100.00 -23.00   1.00   20.00    --  -83.00 119.00  88.00   77
  8  \w    -66.00  -8.00   1.00   20.00    --  -83.00  30.00 -30.00   58
  9  \w     35.00  96.00   1.00   20.00    --  108.36 -94.00   0.00   61
 10  \w     95.00 122.00   1.00   20.00    --  108.36-125.00-180.00   27
 11  \w     32.00  65.00   1.00   20.00    --  108.36 -30.00  90.00   33
 12  \w     79.00 108.00   1.00   20.00    --  108.36 -94.00 -90.00   29
 13  \w     35.00  77.00   1.00   20.00    --  108.36 -45.00 -30.00   42
 14  \w    103.00 154.00   1.00   20.00    --  108.36  30.00   0.00   51
 15  \w     37.00  68.00   1.00   20.00    --  108.36 -30.00-180.00   31
 16  \w     52.00 156.00   1.00   20.00    --  108.36  15.00 -30.00  104
 17  \w     38.00  65.00   1.00   20.00    --  108.36 -30.00  60.00   27
 18  \w     42.00 134.00   1.00   20.00    --  108.36 -77.00  60.00   92
 19  \w     81.00 156.00   1.00   20.00    --  108.36  30.00-150.00   75
 20  \w     33.00  69.00   1.00   20.00    --  108.36 -30.00  30.00   36
 21  \w     36.00  65.00   1.00   20.00    --  108.36 -30.00   0.00   29
 22  \w     63.00 109.00   1.00   20.00    --  108.36 -94.00-150.00   46
 23  \w     35.00  65.00   1.00   20.00    --  108.36 -61.00-180.00   30
 24  \w     73.00 131.00   1.00   20.00    --  108.36 -61.00-180.00   58
 25  \w     68.00 104.00   1.00   20.00    --  108.36 -94.00  30.00   36
 26  \w     43.00  71.00   1.00   20.00    --  108.36 -45.00 -90.00   28
;
_diffrn_measurement_device       'four-circle\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0424737
_diffrn_orient_matrix_UB_12      -0.0499374
_diffrn_orient_matrix_UB_13      -0.0620437
_diffrn_orient_matrix_UB_21      0.0128263
_diffrn_orient_matrix_UB_22      0.1033867
_diffrn_orient_matrix_UB_23      -0.0645429
_diffrn_orient_matrix_UB_31      0.1143129
_diffrn_orient_matrix_UB_32      -0.0054517
_diffrn_orient_matrix_UB_33      0.012043
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.053
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24416
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70
_diffrn_reflns_theta_min         3.297
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    0.729
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.186
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.059
_platon_squeeze_details
;
TITL a20170162_mma225 P -1         R = 0.34
CELL   13.0079   14.5518   18.7581     67.78     76.11     79.56
SPGR P-1
Q101 0.880 0.144 0.157 !       8.01 eA-3
C102 0.558 0.927 0.047 !       6.07 eA-3
C103 0.785 0.822 0.224 !       6.00 eA-3
C104 0.798 0.708 0.130 !       5.94 eA-3
C105 0.906 0.045 0.310 !       5.94 eA-3
Q106 0.738 0.425 0.401 !       5.38 eA-3
C107 0.693 0.741 0.174 !       5.11 eA-3
C108 0.938 0.528 0.059 !       5.08 eA-3
C109 0.497 0.902 0.009 !       4.74 eA-3
C110 0.882 0.800 0.169 !       4.60 eA-3
C111 0.703 0.826 0.184 !       4.45 eA-3
C112 0.951 0.171 0.187 !       4.31 eA-3
C113 0.875 0.684 0.178 !       4.11 eA-3
C114 0.927 0.434 0.068 !       3.85 eA-3
C115 0.654 0.362 0.424 !       3.62 eA-3
C116 0.989 0.098 0.252 !       3.61 eA-3
C117 0.843 0.993 0.284 !       3.43 eA-3
C118 0.985 0.438 0.083 !       3.36 eA-3
C119 0.047 0.568 0.015 !       3.34 eA-3
C120 0.583 0.032 0.011 !       3.02 eA-3
C121 0.737 0.324 0.309 !       2.99 eA-3
C122 0.796 0.088 0.217 !       2.90 eA-3
C123 0.078 0.431 0.252 !       2.82 eA-3
C124 0.099 0.368 0.375 !       2.71 eA-3
C125 0.011 0.764 0.328 !       2.67 eA-3
C126 0.656 0.360 0.342 !       2.67 eA-3
C127 0.812 0.394 0.295 !       2.63 eA-3
C128 0.247 0.041 0.488 !       2.47 eA-3
C129 0.810 0.312 0.333 !       2.31 eA-3
C130 0.110 0.666 0.437 !       2.24 eA-3
C131 0.837 0.376 0.374 !       2.18 eA-3
C132 0.138 0.267 0.295 !       2.08 eA-3
C133 0.081 0.808 0.360 !       2.06 eA-3
C134 0.281 0.954 0.437 !       2.04 eA-3
C135 0.083 0.590 0.407 !       2.00 eA-3
C136 0.037 0.443 0.316 !       1.94 eA-3
C137 0.142 1.004 0.405 !       1.92 eA-3
C138 0.090 0.337 0.250 !       1.92 eA-3
C139 0.797 0.068 0.479 !       1.89 eA-3
C140 0.111 0.288 0.357 !       1.89 eA-3
C141 0.238 0.994 0.369 !       1.85 eA-3
C142 0.108 0.758 0.406 !       1.84 eA-3
C143 0.997 0.773 0.387 !       1.84 eA-3
C144 0.110 0.437 0.314 !       1.83 eA-3
C145 0.880 0.104 0.498 !       1.82 eA-3
C146 0.115 0.350 0.332 !       1.79 eA-3
C147 0.990 0.621 0.408 !       1.61 eA-3
C148 0.063 0.546 0.282 !       1.52 eA-3
C149 0.952 0.669 0.456 !       1.46 eA-3
C150 0.160 0.114 0.390 !       1.39 eA-3
C151 0.035 0.689 0.467 !       1.37 eA-3
C152 0.664 0.285 0.440 !       1.35 eA-3
C153 0.091 0.926 0.440 !       1.32 eA-3
C154 0.169 0.928 0.374 !       1.20 eA-3
C155 0.081 0.105 0.435 !       1.02 eA-3
Q156 0.437 0.150-0.001 !       0.99 eA-3
C157 0.888 0.253 0.139 !       0.84 eA-3
Q158 0.828 0.641 0.234 !       0.83 eA-3
C159 0.573 0.124 0.056 !       0.82 eA-3
C160 0.906 0.057 0.457 !       0.82 eA-3
C161 0.128 1.015 0.484 !       0.81 eA-3
Q162 0.110 0.918 0.091 !       0.80 eA-3
C163 0.813 0.227 0.216 !       0.77 eA-3
Q164 0.409 0.210 0.255 !       0.71 eA-3
Q165 0.331 0.595 0.012 !       0.70 eA-3
C166 0.533 0.054 0.110 !       0.70 eA-3
C167 0.956 0.589 0.328 !       0.68 eA-3
C168 0.341 0.881 0.474 !       0.68 eA-3
Q169 0.531 0.075 0.397 !       0.67 eA-3
Q170 0.294 0.120 0.150 !       0.67 eA-3
Q171 0.891 0.115 0.018 !       0.66 eA-3
Q172 0.436 0.771 0.315 !       0.65 eA-3
Q173 0.329 0.577 0.092 !       0.64 eA-3
Q174 0.765 0.076 0.156 !       0.64 eA-3
Q175 0.238 0.211 0.062 !       0.62 eA-3
Q176 0.236 0.139 0.110 !       0.62 eA-3
Q177 0.729 0.579 0.388 !       0.61 eA-3
Q178 0.911 0.616 0.298 !       0.61 eA-3
Q179 0.489 0.063 0.089 !       0.61 eA-3
Q180 0.715 0.605 0.406 !       0.60 eA-3
C181 0.047 0.354 0.738 !       0.59 eA-3
Q182 0.359 0.507 0.231 !       0.59 eA-3
Q183 0.315 0.442 0.456 !       0.58 eA-3
Q184 0.230 0.187 0.293 !       0.57 eA-3
Q185 0.339 0.171 0.174 !       0.57 eA-3
Q186 0.356 0.232 0.182 !       0.57 eA-3
Q187 0.829 0.816 0.017 !       0.56 eA-3
Q188 0.905 0.084 0.067 !       0.56 eA-3
Q189 0.656 0.404 0.030 !       0.56 eA-3
Q190 0.378 0.490 0.279 !       0.55 eA-3
Q191 0.345 0.453 0.030 !       0.55 eA-3
Q192 0.394 0.607 0.363 !       0.55 eA-3
Q193 0.669 0.728 0.487 !       0.55 eA-3
Q194 0.057 0.983 0.227 !       0.55 eA-3
C195 0.016 0.647 0.237 !       0.55 eA-3
Q196 0.377 0.432 0.272 !       0.54 eA-3
Q197 0.207 0.171 0.044 !       0.54 eA-3
Q198 0.690 0.219 0.349 !       0.54 eA-3
Q199 0.303 0.488 0.466 !       0.54 eA-3
;
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         11965
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0784
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1579P)^2^+1.7606P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2489
_refine_ls_wR_factor_ref         0.2681
_reflns_number_gt                8330
_reflns_number_total             11965
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07383_si_002.cif
_cod_data_source_block           a20170162_mma225_sq
_cod_database_code               4128816
_platon_squeeze_void_probe_radius 1.20