Template-free hierarchical self-assembly of a pyrene derivative into supramolecular nanorods.
El Idrissi, Mohamed; Teat, Simon J.; Corvini, Philippe F.-X.; Paterson, Martin J.; Dalgarno, Scott J.; Shahgaldian, Patrick; Chemical communications (Cambridge, England) 53 (2017) 1973–1976; doi:10.1039/c6cc09731f

data_7119500
_publ_section_title
;
 Template-free hierarchical self-assembly of a pyrene derivative into
 supramolecular nanorods.
;
_journal_issue                   12
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1973
_journal_page_last               1976
_journal_paper_doi               10.1039/c6cc09731f
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety         'C29 H37 N O4 Si'
_chemical_formula_sum            'C29 H37 N O4 Si'
_chemical_formula_weight         491.68
_chemical_name_common            PySi
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-06-05 deposited with the CCDC.
2017-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.678(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.1439(7)
_cell_length_b                   9.6535(3)
_cell_length_c                   30.1293(10)
_cell_measurement_temperature    100(2)
_cell_volume                     5305.1(3)
_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      100(2)
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 with PHOTON 100 detector'
_diffrn_measurement_method       '\f and \w shutterless scans'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.7749
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            36515
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.583
_diffrn_reflns_theta_max         25.583
_diffrn_reflns_theta_min         2.240
_diffrn_source
;
Advanced Light Source, station 11.3.1
;
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.7243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1612 before and 0.0598 after correction.
The Ratio of minimum to maximum transmission is 0.8403.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       Needle
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.855
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Flack x determined using 4474 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.60(6)
_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     1102
_refine_ls_number_reflns         15242
_refine_ls_number_restraints     62
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0975
_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^)+(0.1456P)^2^+14.0875P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2590
_refine_ls_wR_factor_ref         0.2765
_reflns_Friedel_coverage         0.987
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                11900
_reflns_number_total             15242
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc09731f2.cif
_cod_data_source_block           pysi_a6_a
_cod_depositor_comments          'Adding full bibliography for 7119500.cif.'
_cod_database_code               7119500
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.956
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O6-C53 = O7-C55 = O8-C57 = O8A-C57A
 1.45 with sigma of 0.02
 C58A-C57A = C58-C57 = C54-C53 = C56-C55
 1.54 with sigma of 0.02
 Si2-O8 = Si2-O8A = Si2-O6 = Si2-O7
 1.6 with sigma of 0.02
 O4A-C28A = O4-C28 = O3A-C26A = O3-C26 = O2-C24 = O2A-C24A
 1.45 with sigma of 0.02
 C27A-C26A = C27-C26 = C29-C28 = C29A-C28A = C25A-C24A = C25-C24
 1.54 with sigma of 0.02
 Si1-O2 = Si1-O3 = Si1A-O3A = Si1A-O4A = Si1-O4 = Si1A-O2A
 1.6 with sigma of 0.02
 O12-C86A = O12-C86
 1.45 with sigma of 0.02
 C87A-C86A = C87-C86
 1.54 with sigma of 0.02
 Si4-O15 = Si4-O17A = Si4-O16A = Si4-O16
 1.6 with sigma of 0.02
 O15-C111
 1.45 with sigma of 0.02
 C112-C111
 1.54 with sigma of 0.02
 Si4-O17 = Si4-O16 = Si4-O16A = Si4-O15 = Si4-O17A
 1.6 with sigma of 0.02
 O6-C53
 1.45 with sigma of 0.02
 C54-C53
 1.54 with sigma of 0.02
 O15-C111 = O17A-C115 = O17-C113 = O16A-C117
 1.45 with sigma of 0.02
 C114-C113 = C116-C115 = C112-C111
 1.54 with sigma of 0.02
 C118-C117
 1.54 with sigma of 0.02
 Si4-O17A = Si4-O17 = Si4-O16 = Si4-O16A = Si4-O15
 1.6 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C57A) = Uanis(O8A) = Uanis(C58A) = Uanis(C58) = Uanis(O8) = Uanis(C57)
Uanis(C53) = Uanis(C54) = Uanis(O6)
Uanis(O7) = Uanis(C55) = Uanis(C56)
Uanis(C50) = Uanis(C51) = Uanis(C52)
Uanis(C22A) = Uanis(C23A) = Uanis(C23) = Uanis(C21A) = Uanis(N1A) = Uanis(C21)
= Uanis(N1) = Uanis(C22)
Uanis(O3A) = Uanis(O3) = Uanis(C26A) = Uanis(C26) = Uanis(C27A) = Uanis(C27)
Uanis(O2A) = Uanis(C24A) = Uanis(O2) = Uanis(C24) = Uanis(C25) = Uanis(C25A)
Uanis(C97) = Uanis(C93) = Uanis(C88) = Uanis(C92) = Uanis(C102) = Uanis(C91) =
Uanis(C101) = Uanis(C90) = Uanis(C89) = Uanis(C98) = Uanis(C103) = Uanis(C96) =
Uanis(C100) = Uanis(C94) = Uanis(C99) = Uanis(C95)
Uanis(O10) = Uanis(C82) = Uanis(C82A) = Uanis(C83) = Uanis(O10A) = Uanis(C83A)
Uanis(O4A) = Uanis(O4) = Uanis(C29) = Uanis(C28) = Uanis(C28A) = Uanis(C29A)
Uanis(C84) = Uanis(C85A) = Uanis(C84A) = Uanis(O11) = Uanis(C85)
Uanis(C48) = Uanis(C47) = Uanis(C46)
Uanis(O12) = Uanis(C86A) = Uanis(C86) = Uanis(C87A) = Uanis(C87)
Uanis(O15) = Uanis(C111) = Uanis(C112)
Uanis(O16A) = Uanis(C117) = Uanis(O16) = Uanis(C118) = Uanis(C120) = Uanis(C119)
Uanis(O17A) = Uanis(C115) = Uanis(C113) = Uanis(C114) = Uanis(C116) = Uanis(O17)
4. Others
 Fixed Sof: Si1A(0.5) Si1(0.5) O10(0.5) O4A(0.5) C28A(0.5) H28A(0.5) H28B(0.5)
 C82(0.5) H82A(0.5) H82B(0.5) C84(0.5) H84A(0.5) H84B(0.5) O17A(0.5) O2A(0.5)
 C21A(0.5) H21A(0.5) H21B(0.5) C22A(0.5) H22A(0.5) H22B(0.5) N1A(0.5) H1A(0.5)
 C57A(0.5) H57A(0.5) H57B(0.5) O3A(0.5) C24A(0.5) H24A(0.5) H24B(0.5) O2(0.5)
 O8A(0.5) O16A(0.5) C86A(0.5) H86A(0.5) H86B(0.5) O3(0.5) C86(0.5) H86C(0.5)
 H86D(0.5) C23A(0.5) H23A(0.5) H23B(0.5) C115(0.5) H11H(0.5) H11I(0.5)
 C85A(0.5) H85A(0.5) H85B(0.5) H85C(0.5) O4(0.5) C21(0.5) H21C(0.5) H21D(0.5)
 N1(0.5) H1(0.5) C58A(0.5) H58A(0.5) H58B(0.5) H58C(0.5) C117(0.5) H11J(0.5)
 H11K(0.5) C58(0.5) H58D(0.5) H58E(0.5) H58F(0.5) C24(0.5) H24C(0.5) H24D(0.5)
 C29A(0.5) H29A(0.5) H29B(0.5) H29C(0.5) C25(0.5) H25A(0.5) H25B(0.5) H25C(0.5)
 C26A(0.5) H26A(0.5) H26B(0.5) C23(0.5) H23C(0.5) H23D(0.5) C22(0.5) H22C(0.5)
 H22D(0.5) C26(0.5) H26C(0.5) H26D(0.5) O8(0.5) C25A(0.5) H25D(0.5) H25E(0.5)
 H25F(0.5) C27A(0.5) H27A(0.5) H27B(0.5) H27C(0.5) C27(0.5) H27D(0.5) H27E(0.5)
 H27F(0.5) C57(0.5) H57C(0.5) H57D(0.5) C82A(0.5) H82C(0.5) H82D(0.5) C83(0.5)
 H83A(0.5) H83B(0.5) H83C(0.5) O10A(0.5) C83A(0.5) H83D(0.5) H83E(0.5)
 H83F(0.5) C85(0.5) H85D(0.5) H85E(0.5) H85F(0.5) C29(0.5) H29D(0.5) H29E(0.5)
 H29F(0.5) C28(0.5) H28C(0.5) H28D(0.5) C84A(0.5) H84C(0.5) H84D(0.5) C87A(0.5)
 H87A(0.5) H87B(0.5) H87C(0.5) C87(0.5) H87D(0.5) H87E(0.5) H87F(0.5) O16(0.5)
 O17(0.5) C113(0.5) H11L(0.5) H11M(0.5) C114(0.5) H11N(0.5) H11O(0.5) H11P(0.5)
 C116(0.5) H11Q(0.5) H11R(0.5) H11S(0.5) C118(0.5) H11T(0.5) H11U(0.5)
 H11V(0.5) C120(0.5) H12A(0.5) H12B(0.5) H12C(0.5) C119(0.5) H11W(0.5) H11X(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C106(H10A,H10B), C80(H80A,H80B), C19(H19A,
 H19B), C79(H79A,H79B), C77(H77A,H77B), C104(H10C,H10D), C105(H10E,H10F),
 C48(H48A,H48B), C47(H47A,H47B), C108(H10G,H10H), C76(H76A,H76B), C46(H46A,
 H46B), C109(H10I,H10J), C50(H50A,H50B), C75(H75A,H75B), C28A(H28A,H28B),
 C82(H82A,H82B), C51(H51A,H51B), C81(H81A,H81B), C84(H84A,H84B), C110(H11A,
 H11B), C21A(H21A,H21B), C53(H53A,H53B), C22A(H22A,H22B), C55(H55A,H55B),
 C57A(H57A,H57B), C111(H11C,H11D), C24A(H24A,H24B), C86A(H86A,H86B), C86(H86C,
 H86D), C23A(H23A,H23B), C115(H11H,H11I), C52(H52A,H52B), C21(H21C,H21D),
 C117(H11J,H11K), C24(H24C,H24D), C26A(H26A,H26B), C23(H23C,H23D), C22(H22C,
 H22D), C26(H26C,H26D), C57(H57C,H57D), C82A(H82C,H82D), C28(H28C,H28D),
 C84A(H84C,H84D), C113(H11L,H11M), C119(H11W,H11X)
5.b Aromatic/amide H refined with riding coordinates:
 N00B(H00B), N00C(H00C), C8(H8), N00E(H00E), C73(H73), C16(H16), C7(H7),
 C36(H36), C41(H41), C42(H42), C40(H40), C13(H13), C15(H15), C37(H37), C44(H44),
  C12(H12), C45(H45), C102(H102), C74(H74), C11(H11), C32(H32), C2(H2),
 C90(H90), C60(H60), C89(H89), C31(H31), C98(H98), C3(H3), C103(H103), C61(H61),
  C100(H100), C71(H71), C65(H65), C70(H70), C94(H94), C69(H69), C99(H99),
 C95(H95), C66(H66), N1A(H1A), N1(H1)
5.c Idealised Me refined as rotating group:
 C112(H11E,H11F,H11G), C54(H54A,H54B,H54C), C56(H56A,H56B,H56C), C85A(H85A,
 H85B,H85C), C58A(H58A,H58B,H58C), C58(H58D,H58E,H58F), C29A(H29A,H29B,H29C),
 C25(H25A,H25B,H25C), C25A(H25D,H25E,H25F), C27A(H27A,H27B,H27C), C27(H27D,H27E,
 H27F), C83(H83A,H83B,H83C), C83A(H83D,H83E,H83F), C85(H85D,H85E,H85F),
 C29(H29D,H29E,H29F), C87A(H87A,H87B,H87C), C87(H87D,H87E,H87F), C114(H11N,H11O,
 H11P), C116(H11Q,H11R,H11S), C118(H11T,H11U,H11V), C120(H12A,H12B,H12C)
;
_shelx_res_checksum              93441
_shelx_hkl_checksum              79229
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'