Tetraarylpyrrolo[3,2-b]pyrroles as versatile and responsive fluorescent linkers in metal-organic frameworks.
Hawes, Chris S.; Ó Máille, Gearóid M; Byrne, Kevin; Schmitt, Wolfgang; Gunnlaugsson, Thorfinnur; Dalton transactions (Cambridge, England : 2003) 47 (2018) 10080–10092; doi:10.1039/c8dt01784k

data_7702203
_publ_section_title
;
 Tetraarylpyrrolo[3,2-b]pyrroles as versatile and responsive fluorescent
 linkers in metal-organic frameworks.
;
_journal_issue                   30
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10080
_journal_page_last               10092
_journal_paper_doi               10.1039/c8dt01784k
_journal_volume                  47
_journal_year                    2018
_chemical_formula_moiety         'C120 H108 N6 O13 Zn4'
_chemical_formula_sum            'C120 H108 N6 O13 Zn4'
_chemical_formula_weight         2103.60
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-01-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-01-23 deposited with the CCDC.
2018-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                89.484(2)
_cell_angle_beta                 75.944(2)
_cell_angle_gamma                87.829(2)
_cell_formula_units_Z            2
_cell_length_a                   22.5696(8)
_cell_length_b                   22.7345(8)
_cell_length_c                   22.7582(8)
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      54.196
_cell_measurement_theta_min      2.47
_cell_volume                     11319.7(7)
_computing_cell_refinement       'SAINT V8.35A (2016)'
_computing_data_reduction        'SAINT V8.35A (2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            63193
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        54.336
_diffrn_reflns_theta_max         54.336
_diffrn_reflns_theta_min         1.945
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  0.7507
_exptl_absorpt_correction_T_min  0.6451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0581 before and 0.0467 after correction. The Ratio of minimum to maximum transmission is 0.8593. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    0.617
_exptl_crystal_description       block
_exptl_crystal_F_000             2188
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1225
_refine_ls_number_reflns         27389
_refine_ls_number_restraints     388
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0700
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1677P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2148
_refine_ls_wR_factor_ref         0.2307
_reflns_Friedel_coverage         0.000
_reflns_number_gt                18928
_reflns_number_total             27389
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt01784k2.cif
_cod_data_source_block           2
_cod_database_code               7702203
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.893
_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
2. Restrained distances
 C61-C63
 2.6 with sigma of 0.02
 C62-C61
 2.6 with sigma of 0.02
 C62-C63
 2.6 with sigma of 0.02
 N5-C89
 2.298 with sigma of 0.02
 C88-C90
 2.298 with sigma of 0.02
 C89-C91
 2.298 with sigma of 0.02
 C90-N5
 2.298 with sigma of 0.02
 C111-N6
 1.41 with sigma of 0.02
 C112-N6
 2.41 with sigma of 0.02
 C116-N6
 2.41 with sigma of 0.02
 C104-C103 = C104-C101 = C104-C102
 1.5 with sigma of 0.02
 C103-C102
 2.57 with sigma of 0.02
 C101-C102
 2.57 with sigma of 0.02
 C101-C103
 2.57 with sigma of 0.02
 C118-C120
 2.57 with sigma of 0.02
 C118-C117
 1.5 with sigma of 0.02
 C113-C117
 2.6 with sigma of 0.02
 C117-C115
 2.6 with sigma of 0.02
 N5-C107
 2.41 with sigma of 0.02
 N5-C109
 2.41 with sigma of 0.02
 C108-N5
 1.41 with sigma of 0.02
 C104-C105
 1.55 with sigma of 0.02
 C106-C102
 2.9 with sigma of 0.02
 C104-C110
 2.6 with sigma of 0.02
 C106-C104
 2.6 with sigma of 0.02
 C106-C103
 2.9 with sigma of 0.02
 C105-C103
 2.46 with sigma of 0.02
 C102-C105
 2.46 with sigma of 0.02
 C101-C105
 2.46 with sigma of 0.02
 C118-C119
 2.57 with sigma of 0.01
 C119-C120
 2.57 with sigma of 0.01
 C117-C114 = C119-C117 = C117-C120
 1.5 with sigma of 0.02
 C61-C64 \\sim C62-C64 \\sim C63-C64
 with sigma of 0.01
 C23-C24 \\sim C22-C24 \\sim C21-C24
 with sigma of 0.01
3. Restrained planarity
 C104, C105, C106, C110
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C91) \\sim Ueq, Uanis(C90) \\sim Ueq, Uanis(N6) \\sim Ueq, Uanis(C93)
\\sim Ueq, Uanis(C89) \\sim Ueq, Uanis(C88) \\sim Ueq, Uanis(C92) \\sim Ueq,
Uanis(N5) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(C107) \\sim Ueq, Uanis(C109) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.02
Uanis(C21) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C23) \\sim Ueq: with sigma of
0.02 and sigma for terminal atoms of 0.02
Uanis(C105) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(C61) \\sim Ueq, Uanis(C62) \\sim Ueq, Uanis(C64) \\sim Ueq, Uanis(C63)
\\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(C111) = Uanis(C116) = Uanis(C115) = Uanis(C114) = Uanis(C113) =
Uanis(C112)
5. Rigid body (RIGU) restrains
 C91, C90, N6, C93, C92, C89, C88, N5, C111, C116, C115, C114, C113, C112,
 C102, C120, C110, C105, C106, C107, C108, C109, C103, C101, C104, C118, C117,
 C119
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6.a Me refined with riding coordinates:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C31(H31A,H31B,
 H31C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C61(H61A,H61B,H61C), C62(H62A,
 H62B,H62C), C63(H63A,H63B,H63C), C71(H71A,H71B,H71C), C72(H72A,H72B,H72C),
 C73(H73A,H73B,H73C), C101(H10A,H10B,H10C), C102(H10D,H10E,H10F), C103(H10G,
 H10H,H10I), C118(H11A,H11B,H11C), C119(H11D,H11E,H11F), C120(H12A,H12B,H12C)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C12(H12), C15(H15), C16(H16),
 C18(H18), C19(H19), C26(H26), C27(H27), C29(H29), C30(H30), C36(H36), C37(H37),
  C39(H39), C40(H40), C43(H43), C44(H44), C46(H46), C47(H47), C49(H49),
 C52(H52), C55(H55), C56(H56), C58(H58), C59(H59), C66(H66), C67(H67), C69(H69),
  C70(H70), C76(H76), C77(H77), C79(H79), C80(H80), C83(H83), C84(H84),
 C86(H86), C87(H87), C89(H89), C92(H92), C95(H95), C96(H96), C98(H98), C99(H99),
  C110(H110), C106(H106), C107(H107), C109(H109), C116(H116), C115(H115),
 C113(H113), C112(H112)
6.c Fitted pentagon refined as free rotating group:
 C91(C90,N6,C93,C92)
6.d Fitted hexagon refined as free rotating group:
 C110(C105,C106,C107,C108,C109), C111(C116,C115,C114,C113,C112)
;
_shelx_res_checksum              9292
_shelx_fab_checksum              24145
_olex2_submission_special_instructions 'No special instructions were received'