The role of indolyl substituents in squaramide-based anionophores
Caltagirone, Claudia; Picci, Giacomo; Quesada, Roberto; Carreira-Barral, Israel; Alonso-Carrillo, Daniel; Milia, Jessica; Busonera, Chiara; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01444K

data_7158895
_publ_section_title
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 The role of indolyl substituents in squaramide-based anionophores
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01444K
_journal_year                    2022
_chemical_formula_moiety
'0.5(Cl), 0.5(C20 H11 F6 N3 O2), 0.5(C16 H36 N)'
_chemical_formula_sum            'C18 H23.5 Cl0.5 F3 N2 O'
_chemical_formula_weight         358.61
_chemical_name_systematic        L6.TBACl
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-08-04 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                94.201(2)
_cell_angle_beta                 112.935(2)
_cell_angle_gamma                119.0850(10)
_cell_formula_units_Z            8
_cell_length_a                   16.7881(5)
_cell_length_b                   16.8007(5)
_cell_length_c                   17.4748(5)
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    240(2)
_cell_measurement_theta_max      64.59
_cell_measurement_theta_min      2.90
_cell_volume                     3749.5(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      240(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            101170
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.735
_diffrn_reflns_theta_max         66.735
_diffrn_reflns_theta_min         2.905
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.472
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1063 before and 0.0710 after correction.
The Ratio of minimum to maximum transmission is 0.7917.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1004
_refine_ls_number_reflns         13224
_refine_ls_number_restraints     372
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.0703
_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^)+(0.1147P)^2^+2.2625P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1845
_refine_ls_wR_factor_ref         0.2541
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7627
_reflns_number_total             13224
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01444k2.cif
_cod_data_source_block           L6TBACl
_cod_original_formula_sum        'C18 H23.50 Cl0.50 F3 N2 O'
_cod_database_code               7158895
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.757
_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
 F6-F4 \\sim F6-F5 \\sim F6A-F4A \\sim F6A-F5A \\sim F4A-F5A \\sim F4-F5
 with sigma of 0.04
 C20-C17 \\sim C20-F6 \\sim C20-F6A \\sim C20-F4A \\sim C20-F5A \\sim C20-F4
\\sim C20-F5
 with sigma of 0.02
 C19-F2 \\sim C19-C15 \\sim C19-F3 \\sim C19-F1A \\sim C19-F2A \\sim C19-F3A
\\sim C19-F1
 with sigma of 0.02
 F2-F3 \\sim F2-F1 \\sim F3-F1 \\sim F1A-F2A \\sim F1A-F3A \\sim F2A-F3A
 with sigma of 0.04
 F11-F12 \\sim F11-F10 \\sim F12-F10 \\sim F11A-F10A \\sim F11A-F12A \\sim
F10A-F12A
 with sigma of 0.04
 C40-F11 \\sim C40-F12 \\sim C40-F10 \\sim C40-F11A \\sim C40-F10A \\sim
C40-F12A \\sim C40-C37
 with sigma of 0.02
 F8-F7 \\sim F8-F9 \\sim F7-F9 \\sim F7A-F8A \\sim F7A-F9A \\sim F8A-F9A
 with sigma of 0.04
 C39-F8 \\sim C39-F7 \\sim C39-F9 \\sim C39-F7A \\sim C39-F8A \\sim C39-F9A
\\sim C39-C35
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 F6, F5, F4, C20, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F6A, F5A, F4A, C20, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F2A, F1A, F3A, C19, C15
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F3, F1, F2, C19, C15
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F10, F11, F12, C40, C37
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F12A, F11A, F10A, C40, C37
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F8A, F7A, F9A, C39, C35
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F7, F8, F9, C39, C35
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F6A)=Sof(F4A)=Sof(F5A)=1-FVAR(1)
 Sof(F6)=Sof(F4)=Sof(F5)=FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(2)
 Sof(F3)=Sof(F2)=Sof(F1)=FVAR(2)
 Sof(F11A)=Sof(F10A)=Sof(F12A)=1-FVAR(3)
 Sof(F11)=Sof(F12)=Sof(F10)=FVAR(3)
 Sof(F7A)=Sof(F8A)=Sof(F9A)=1-FVAR(4)
 Sof(F8)=Sof(F7)=Sof(F9)=FVAR(4)
5.a Secondary CH2 refined with riding coordinates:
 C61(H61A,H61B), C62(H62A,H62B), C52(H52A,H52B), C53(H53A,H53B), C68(H68A,
 H68B), C44(H44A,H44B), C60(H60A,H60B), C69(H69A,H69B), C70(H70A,H70B),
 C59(H59A,H59B), C43(H43A,H43B), C63(H63A,H63B), C67(H67A,H67B), C45(H45A,H45B),
  C58(H58A,H58B), C71(H71A,H71B), C54(H54A,H54B), C51(H51A,H51B), C42(H42A,
 H42B), C46(H46A,H46B), C55(H55A,H55B), C50(H50A,H50B), C66(H66A,H66B),
 C47(H47A,H47B)
5.b Aromatic/amide H refined with riding coordinates:
 N5(H5), N2(H2), N3(H3), N6(H6), N4(H4), N1(H1), C18(H18), C14(H14), C26(H26),
 C38(H38), C34(H34), C24(H24), C6(H6A), C25(H25), C16(H16), C21(H21), C4(H4A),
 C5(H5A), C22(H22), C36(H36), C1(H1A), C2(H2A)
5.c Idealised Me refined as rotating group:
 C64(H64A,H64B,H64C), C57(H57A,H57B,H57C), C41(H41A,H41B,H41C), C72(H72A,H72B,
 H72C), C49(H49A,H49B,H49C), C56(H56A,H56B,H56C), C65(H65A,H65B,H65C), C48(H48A,
 H48B,H48C)
;
_shelx_res_checksum              26694
_olex2_submission_special_instructions 'No special instructions were received'