Aromatic Oligoamide Foldamers as Versatile Scaffolds for Induced Circularly Polarized Luminescence at Adjustable Wavelengths
Merlet, Eric; Moreno, Kevin; Tron, Arnaud; McClenaghan, Nathan D.; Kauffmann, Brice; Ferrand, Yann; OLIVIER, Céline; Chemical Communications  (2019) –; doi:10.1039/C9CC04697F

data_7123907
_publ_section_title
;
 Aromatic Oligoamide Foldamers as Versatile Scaffolds for Induced
 Circularly Polarized Luminescence at Adjustable Wavelengths
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC04697F
_journal_year                    2019
_chemical_formula_moiety         '2(C H Cl3), C83 H75 N9 O10'
_chemical_formula_sum            'C85 H77 Cl6 N9 O10'
_chemical_formula_weight         1597.25
_chemical_properties_physical    Light-sensitive
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-18 deposited with the CCDC.    2019-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                109.695(5)
_cell_angle_beta                 98.506(4)
_cell_angle_gamma                100.557(4)
_cell_formula_units_Z            2
_cell_length_a                   13.2948(5)
_cell_length_b                   18.1431(10)
_cell_length_c                   20.1869(9)
_cell_measurement_reflns_used    11404
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.7000
_cell_measurement_theta_min      3.4300
_cell_volume                     4389.7(4)
_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
_diffrn_detector                 'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.967
_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   -195.00 -15.00   1.00   20.00    -- -105.00  12.00 108.00  180
  2  \w    -60.00 -14.00   1.00    1.00    --    5.00  12.00-180.00   46
  3  \w   -195.00 -15.00   1.00   20.00    -- -105.00  60.00 -72.00  180
  4  \w   -195.00 -15.00   1.00   20.00    -- -105.00  60.00 108.00  180
  5  \w   -131.00  49.00   1.00    5.00    --  -41.00  60.00 -72.00  180
  6  \w   -195.00 -15.00   1.00   20.00    -- -105.00  60.00   0.00  180
  7  \w    -91.00  49.00   1.00    5.00    --  -41.00  60.00-180.00  140
  8  \w   -169.00 -15.00   1.00   20.00    -- -105.00  60.00-180.00  154
  9  \w   -195.00 -33.00   1.00   20.00    -- -105.00  12.00 -72.00  162
 10  \w   -100.00  49.00   1.00    5.00    --  -41.00  48.00  72.00  149
 11  \w   -167.00 -33.00   1.00   20.00    -- -105.00  60.00  72.00  134
 12  \w   -137.00 -29.00   1.00   20.00    -- -105.00  48.00 -36.00  108
 13  \w   -171.00 -59.00   1.00   20.00    -- -105.00  60.00-144.00  112
 14  \w   -174.00-106.00   1.00   20.00    -- -105.00  48.00 144.00   68
 15  \w   -160.00 -33.00   1.00   20.00    -- -105.00  60.00  36.00  127
 16  \w    -44.00  49.00   1.00    5.00    --  -41.00  60.00-108.00   93
 17  \w   -117.00 -55.00   1.00    5.00    --  -41.00  36.00  36.00   62
 18  \w   -160.00 -83.00   1.00   20.00    -- -105.00  36.00 144.00   77
 19  \w   -165.00 -96.00   1.00   20.00    -- -105.00  60.00-108.00   69
 20  \w    -26.00  49.00   1.00    5.00    --  -41.00  60.00   0.00   75
 21  \w   -164.00 -95.00   1.00   20.00    -- -105.00  60.00 -36.00   69
 22  \w   -164.00-119.00   1.00   20.00    -- -105.00  60.00 144.00   45
 23  \w      4.00  49.00   1.00    5.00    --  -41.00  60.00  72.00   45
 24  \w   -195.00 -35.00   1.00   20.00    -- -105.00  36.00   0.00  160
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0487779000
_diffrn_orient_matrix_UB_12      0.0842929000
_diffrn_orient_matrix_UB_13      0.0596333000
_diffrn_orient_matrix_UB_21      -0.0211125000
_diffrn_orient_matrix_UB_22      -0.0349855000
_diffrn_orient_matrix_UB_23      0.0577899000
_diffrn_orient_matrix_UB_31      0.1087217000
_diffrn_orient_matrix_UB_32      -0.0186584000
_diffrn_orient_matrix_UB_33      0.0054512000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            62904
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.529
_diffrn_reflns_theta_min         2.387
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Rigaku FRX (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.266
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       plate
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.219
_refine_diff_density_min         -1.151
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.0005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1003
_refine_ls_number_reflns         17124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.172
_refine_ls_R_factor_all          0.1404
_refine_ls_R_factor_gt           0.1084
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3137
_refine_ls_wR_factor_ref         0.3534
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10480
_reflns_number_total             17124
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04697f2.cif
_cod_data_source_block           co_full
_cod_database_code               7123907
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C60 H80 N10 O12 Cl9'
_reflns_odcompleteness_completeness 96.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     73.37
_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.a Ternary CH refined with riding coordinates:
 C01V(H01V), C02B(H1AA), C02Z(H0AA), C034(H034), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C01J(H01G,H01H), C02P(H02P,H02Q), C02U(H02W,H02X)
2.c Aromatic/amide H refined with riding coordinates:
 N00D(H00D), N00I(H00I), N00J(H00J), C011(H011), C01A(H01D), C01B(H01E),
 C01D(H01F), C01K(H01K), C01L(H01L), C01N(H01N), C01P(H01P), C01R(H01R),
 C01T(H01T), C01W(H01W), C01X(H01X), C01Y(H01Y), C01Z(H01Z), C023(H023),
 C024(H024), C026(H026), C027(H027), C02C(H02C), C02E(H02E), C02H(H02H),
 C02K(H02K), C02M(H02M), C02N(H02N), C02Q(H02R), C02T(H02V), C02V(H02Y),
 C02X(H02Z), C02Y(H02), C030(H030)
2.d Idealised Me refined as rotating group:
 C017(H01A,H01B,H01C), C02J(H02A,H02B,H02D), C02L(H02F,H02G,H02I), C02O(H02J,
 H02L,H02O), C02R(H02S,H02T,H02U), C031(H03A,H03B,H03C), C032(H03D,H03E,H03F),
 C033(H03G,H03H,H03I), C035(H03J,H03K,H03L), C036(H03M,H03N,H03O), C4(H4A,H4B,
 H4C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.807
_oxdiff_exptl_absorpt_empirical_full_min 0.539