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_7158894
_publ_section_title
;
 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         'C12 H11 N2 O, C2 H4 O'
_chemical_formula_sum            'C14 H15 N2 O2'
_chemical_formula_weight         243.28
_chemical_name_systematic        L4
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-03-23
_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                90
_cell_angle_beta                 107.034(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.691(4)
_cell_length_b                   6.0862(9)
_cell_length_c                   18.277(3)
_cell_measurement_reflns_used    1527
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      63.58
_cell_measurement_theta_min      3.90
_cell_volume                     2519.7(7)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.729
_diffrn_measured_fraction_theta_max 0.729
_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  0.0748
_diffrn_reflns_av_unetI/netI     0.0830
_diffrn_reflns_Laue_measured_fraction_full 0.729
_diffrn_reflns_Laue_measured_fraction_max 0.729
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2646
_diffrn_reflns_point_group_measured_fraction_full 0.729
_diffrn_reflns_point_group_measured_fraction_max 0.729
_diffrn_reflns_theta_full        64.314
_diffrn_reflns_theta_max         64.314
_diffrn_reflns_theta_min         3.903
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_T_max  0.7525
_exptl_absorpt_correction_T_min  0.5478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1100 before and 0.0442 after correction.
The Ratio of minimum to maximum transmission is 0.7280.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1537
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0951
_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^)+(0.1802P)^2^+2.3980P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2890
_refine_ls_wR_factor_ref         0.3177
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1126
_reflns_number_total             1537
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01444k2.cif
_cod_data_source_block           L4
_cod_database_code               7158894
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.872
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C9(H9A,H9B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C1(H1A), C4(H4), C6(H6), C5(H5), C3(H3)
;
_shelx_res_checksum              94648
_olex2_submission_special_instructions 'No special instructions were received'