Stapled helical o-OPE foldamers as new circularly polarized luminescence emitters based on carbophilic interactions with Ag(i)-sensitivity
Morcillo, Sara P.; Miguel, Delia; Álvarez de Cienfuegos, Luis; Justicia, José; Abbate, Sergio; Castiglioni, Ettore; Bour, Christophe; Ribagorda, María; Cárdenas, Diego J.; Paredes, José Manuel; Crovetto, Luis; Choquesillo-Lazarte, Duane; Mota, Antonio J.; Carreño, M. Carmen; Longhi, Giovanna; Cuerva, Juan M.; Chem. Sci. 7 (2016) 5663–; doi:10.1039/C6SC01808D

data_1543334
_publ_section_title
;
 Stapled helical o-OPE foldamers as new circularly polarized luminescence
 emitters based on carbophilic interactions with Ag(i)-sensitivity
;
_journal_issue                   9
_journal_name_full               'Chem. Sci.'
_journal_page_first              5663
_journal_paper_doi               10.1039/C6SC01808D
_journal_volume                  7
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C54 H48 O10, 2(C5 H9 O)'
_chemical_formula_sum            'C64 H66 O12'
_chemical_formula_weight         1027.16
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-10-20
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2015-12-17 deposited with the CCDC.
2016-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.299(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.2027(5)
_cell_length_b                   11.5719(5)
_cell_length_c                   18.2672(8)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.653
_cell_measurement_theta_min      3.933
_cell_volume                     2774.0(2)
_computing_cell_refinement       'Bruker Apex2, 2014'
_computing_data_collection       'Bruker Apex2, 2014'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            43250
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.726
_diffrn_reflns_theta_min         3.368
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1171 before and 0.0685 after correction.
The Ratio of minimum to maximum transmission is 0.8915.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       block
_exptl_crystal_F_000             1092
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: tetrahydropyran'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 3802 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_coef       0.0057(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     692
_refine_ls_number_reflns         9663
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0476P)^2^+0.6742P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                8869
_reflns_number_total             9663
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc01808d2.cif
_cod_data_source_block           sp228_1
_cod_depositor_comments          'Adding full bibliography for 1543334.cif.'
_cod_database_code               1543334
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.935
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C35(H35), C51(H51)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C34(H34A,H34B), C45(H45A,H45B), C46(H46A,H46B), C60(H60A,H60B),
 C61(H61A,H61B), C01W(H01A,H01B), C68(H68A,H68B), C69(H69A,H69B), C70(H70A,
 H70B), C73(H73A,H73B), C74(H74A,H74B), C75(H75A,H75B), C76(H76A,H76B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15),
 C20(H20), C21(H21), C22(H22), C23(H23), C28(H28), C29(H29), C30(H30), C32(H32),
  C67(H67), C72(H72)
2.d Idealised Me refined as rotating group:
 C44(H44A,H44B,H44C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C59(H59A,H59B,
 H59C), C63(H63A,H63B,H63C), C64(H64A,H64B,H64C)
;
_olex2_submission_special_instructions 'No special instructions were received'