Defying strain in the synthesis of an electroactive bilayer helicene
Milton, Margarita; Schuster, Nathaniel J.; Paley, Daniel W.; Hernández Sánchez, Raúl; Ng, Fay; Steigerwald, Michael L.; Nuckolls, Colin; Chemical Science  (2019) –; doi:10.1039/C8SC04216K

data_1550263
_publ_section_title
;
 Defying strain in the synthesis of an electroactive bilayer helicene
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC04216K
_journal_year                    2019
_chemical_formula_moiety         'C116 H130 N4 O10, C7 H5 F3'
_chemical_formula_sum            'C123 H135 F3 N4 O10'
_chemical_formula_weight         1886.34
_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
_audit_creation_date             2018-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-19 deposited with the CCDC.
2018-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                68.468(15)
_cell_angle_beta                 77.568(14)
_cell_angle_gamma                82.152(13)
_cell_formula_units_Z            2
_cell_length_a                   16.011(3)
_cell_length_b                   17.232(3)
_cell_length_c                   19.864(3)
_cell_measurement_reflns_used    1535
_cell_measurement_temperature    99.8(5)
_cell_measurement_theta_max      37.9660
_cell_measurement_theta_min      3.8120
_cell_volume                     4968.5(16)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.8(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_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   -110.00 -35.00   1.00   10.00    --  -37.78-178.00 -60.00   75
  2  \w    -57.00  31.00   1.00   10.00    --  -37.78  37.00 -90.00   88
  3  \w   -105.00 -11.00   1.00   10.00    --  -37.78 -77.00  90.00   94
  4  \w   -105.00 -11.00   1.00   10.00    --  -37.78 -77.00 120.00   94
  5  \w   -109.00  -8.00   1.00   10.00    --  -37.78 -19.00 -90.00  101
  6  \w   -105.00 -11.00   1.00   10.00    --  -37.78 -77.00-120.00   94
  7  \w      1.00  77.00   1.00   10.00    --   37.78 -99.00-180.00   76
  8  \w     44.00 111.00   1.00   10.00    --   37.78-162.00 119.00   67
  9  \w      1.00  77.00   1.00   10.00    --   37.78 -99.00 -30.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0523121000
_diffrn_orient_matrix_UB_12      -0.0604841000
_diffrn_orient_matrix_UB_13      0.0569967000
_diffrn_orient_matrix_UB_21      0.0617140000
_diffrn_orient_matrix_UB_22      -0.0236837000
_diffrn_orient_matrix_UB_23      -0.0615430000
_diffrn_orient_matrix_UB_31      0.0565897000
_diffrn_orient_matrix_UB_32      0.0710993000
_diffrn_orient_matrix_UB_33      -0.0120741000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0894
_diffrn_reflns_av_unetI/netI     0.1413
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13770
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        38.959
_diffrn_reflns_theta_max         38.959
_diffrn_reflns_theta_min         3.386
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.028
_exptl_crystal_size_min          0.019
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     687
_refine_ls_number_reflns         5376
_refine_ls_number_restraints     101
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1781
_refine_ls_R_factor_gt           0.0960
_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^)+(0.1581P)^2^+1.9594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2316
_refine_ls_wR_factor_ref         0.2985
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2780
_reflns_number_total             5376
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc04216k2.cif
_cod_data_source_block           rhs46_dp
_cod_original_cell_volume        4968.3(15)
_cod_database_code               1550263
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'c123 h135 f3 n4 o10'
_reflns_odcompleteness_completeness 91.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     39.58
_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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1A with sigma of 0.01 and sigma
for terminal atoms of 0.02
C16_2 \\sim C17B_2 \\sim C18B_2 \\sim C19B_2 \\sim C20B_2 \\sim C21B_2 \\sim
C22B_2 \\sim C23B_2 \\sim C24B_2 \\sim C25B_2 \\sim C26B_2: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08
3. Same fragment restrains
{C16_2, C17B_2, C18B_2, C19B_2, C20B_2, C21B_2, C22B_2, C23B_2, C24B_2, C25B_2,
C26B_2} sigma for 1-2: 0.02, 1-3: 0.04
as
{C16_2, C17_2, C18_2, C19_2, C20_2, C21_2, C22_2, C23_2, C24_2, C25_2, C26_2}
{C16_3, C17_3, C18_3, C19_3, C20_3, C21_3, C22B_3, C23B_3, C24B_3, C25B_3,
C26B_3} sigma for 1-2: 0.02, 1-3: 0.04
as
{C16_3, C17_3, C18_3, C19_3, C20_3, C21_3, C22_3, C23_3, C24_3, C25_3, C26_3}
{O15_5, C16B_5, C17B_5, C18B_5, C19B_5, C20B_5} sigma for 1-2: 0.02, 1-3: 0.04
as
{O15_5, C16_5, C17_5, C18_5, C19_5, C20_5}
{O21_5, C22B_5, C23B_5, C24B_5, C25B_5, C26B_5} sigma for 1-2: 0.02, 1-3: 0.04
{O21_5, C22C_5, C23C_5, C24C_5, C25C_5, C26C_5} sigma for 1-2: 0.02, 1-3: 0.04
as
{O21_5, C22_5, C23_5, C24_5, C25_5, C26_5}
4. Others
 1*[Sof(C22)+Sof(H22A)+Sof(H22B)+Sof(C23)+Sof(H23A)+Sof(H23B)+Sof(C24)+
 Sof(H24A)+Sof(H24B)+Sof(C25)+Sof(H25A)+Sof(H25B)+Sof(C26)+Sof(H26A)+Sof(H26B)+
 Sof(H26C)]+1*[Sof(C22B)+Sof(H22C)+Sof(H22D)+Sof(C23B)+Sof(H23C)+Sof(H23D)+
 Sof(C24B)+Sof(H24C)+Sof(H24D)+Sof(C25B)+Sof(H25C)+Sof(H25D)+Sof(C26B)+
 Sof(H26D)+Sof(H26E)+Sof(H26F)]+1*[Sof(C22C)+Sof(H22E)+Sof(H22F)+Sof(C23C)+
 Sof(H23E)+Sof(H23F)+Sof(C24C)+Sof(H24E)+Sof(H24F)+Sof(C25C)+Sof(H25E)+
 Sof(H25F)+Sof(C26C)+Sof(H26G)+Sof(H26H)+Sof(H26I)]=1 with esd of 0.001
 Sof(H16B)=Sof(C17B)=Sof(H17C)=Sof(H17D)=Sof(C18B)=Sof(H18C)=Sof(H18D)=
 Sof(C19B)=Sof(H19C)=Sof(H19D)=Sof(C20B)=Sof(H20C)=Sof(H20D)=Sof(C21B)=
 Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C22B)=Sof(H22C)=Sof(H22D)=Sof(C23B)=
 Sof(H23C)=Sof(H23D)=Sof(C24B)=Sof(H24C)=Sof(H24D)=Sof(C25B)=Sof(H25C)=
 Sof(H25D)=Sof(C26B)=Sof(H26D)=Sof(H26E)=Sof(H26F)=1-FVAR(1)
 Sof(H16)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(C19)=
 Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C21)=Sof(H21A)=Sof(H21B)=
 Sof(H21C)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)=
 Sof(H24A)=Sof(H24B)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=
 Sof(H26C)=FVAR(1)
 Sof(H16B)=Sof(C22B)=Sof(H22C)=Sof(H22D)=Sof(C23B)=Sof(H23C)=Sof(H23D)=
 Sof(C24B)=Sof(H24C)=Sof(H24D)=Sof(C25B)=Sof(H25C)=Sof(H25D)=Sof(C26B)=
 Sof(H26D)=Sof(H26E)=Sof(H26F)=1-FVAR(2)
 Sof(H16)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)=
 Sof(H24A)=Sof(H24B)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=
 Sof(H26C)=FVAR(2)
 Sof(C16B)=Sof(H16C)=Sof(H16D)=Sof(C17B)=Sof(H17C)=Sof(H17D)=Sof(C18B)=
 Sof(H18C)=Sof(H18D)=Sof(C19B)=Sof(H19C)=Sof(H19D)=Sof(C20B)=Sof(H20D)=
 Sof(H20E)=Sof(H20F)=1-FVAR(3)
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(C18)=Sof(H18A)=
 Sof(H18B)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=
 FVAR(3)
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=
 Sof(H24B)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=
 FVAR(4)
 Sof(C22B)=Sof(H22C)=Sof(H22D)=Sof(C23B)=Sof(H23C)=Sof(H23D)=Sof(C24B)=
 Sof(H24C)=Sof(H24D)=Sof(C25B)=Sof(H25C)=Sof(H25D)=Sof(C26B)=Sof(H26D)=
 Sof(H26E)=Sof(H26F)=FVAR(5)
 Sof(C22C)=Sof(H22E)=Sof(H22F)=Sof(C23C)=Sof(H23E)=Sof(H23F)=Sof(C24C)=
 Sof(H24E)=Sof(H24F)=Sof(C25C)=Sof(H25E)=Sof(H25F)=Sof(C26C)=Sof(H26G)=
 Sof(H26H)=Sof(H26I)=FVAR(6)
5.a Ternary CH refined with riding coordinates:
 C16(H16), C16(H16), C16(H16B), C16(H16), C16(H16B), C16(H16)
5.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C22(H22A,
 H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C17(H17A,H17B),
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C22(H22A,H22B), C23(H23A,H23B),
  C24(H24A,H24B), C25(H25A,H25B), C17B(H17C,H17D), C18B(H18C,H18D), C19B(H19C,
 H19D), C20B(H20C,H20D), C22B(H22C,H22D), C23B(H23C,H23D), C24B(H24C,H24D),
 C25B(H25C,H25D), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,
 H20B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B),
 C22B(H22C,H22D), C23B(H23C,H23D), C24B(H24C,H24D), C25B(H25C,H25D), C17(H17A,
 H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C22(H22A,H22B),
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C16(H16A,H16B), C17(H17A,H17B),
  C18(H18A,H18B), C19(H19A,H19B), C16B(H16C,H16D), C17B(H17C,H17D), C18B(H18C,
 H18D), C19B(H19C,H19D), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B),
 C25(H25A,H25B), C22B(H22C,H22D), C23B(H23C,H23D), C24B(H24C,H24D), C25B(H25C,
 H25D), C22C(H22E,H22F), C23C(H23E,H23F), C24C(H24E,H24F), C25C(H25E,H25F)
5.c Me refined with riding coordinates:
 C21(H21A,H21B,H21C), C26(H26A,H26B,H26C), C21(H21A,H21B,H21C), C26(H26A,H26B,
 H26C), C21B(H21D,H21E,H21F), C26B(H26D,H26E,H26F), C21(H21A,H21B,H21C),
 C26(H26A,H26B,H26C), C26B(H26D,H26E,H26F), C21(H21A,H21B,H21C), C26(H26A,H26B,
 H26C), C20(H20A,H20B,H20C), C20B(H20D,H20E,H20F), C26(H26A,H26B,H26C),
 C26B(H26D,H26E,H26F), C26C(H26G,H26H,H26I)
5.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C9(H9), C3(H3), C8(H8), C9(H9), C3(H3), C8(H8), C9(H9),
 C3(H3), C8(H8), C9(H9), C3(H3), C4(H4), C9(H9), C10(H10), C6(H6), C7(H7),
 C8(H8), C9(H9), C10(H10)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.362
_oxdiff_exptl_absorpt_empirical_full_min 0.825