Croconamides: a new dual hydrogen bond donating motif for anion recognition and organocatalysis.
Jeppesen, Anne; Nielsen, Bjarne E.; Larsen, Dennis; Akselsen, Olivia M.; Sølling, Theis I; Brock-Nannestad, Theis; Pittelkow, Michael; Organic & biomolecular chemistry 15 (2017) 2784–2790; doi:10.1039/c7ob00441a

data_7155508
_publ_section_title
;
 Croconamides: a new dual hydrogen bond donating motif for anion
 recognition and organocatalysis.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2784
_journal_page_last               2790
_journal_paper_doi               10.1039/c7ob00441a
_journal_volume                  15
_journal_year                    2017
_chemical_formula_moiety         'C21 H8 F12 N2 O3'
_chemical_formula_sum            'C21 H8 F12 N2 O3'
_chemical_formula_weight         564.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-12-15 deposited with the CCDC.
2017-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 122.816(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.0339(13)
_cell_length_b                   8.9046(7)
_cell_length_c                   13.8902(10)
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.59
_cell_volume                     2082.5(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      123.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0952
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            45150
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.015
_diffrn_reflns_theta_min         2.419
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1633 before and 0.1063 after correction.
The Ratio of minimum to maximum transmission is 0.7854.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.681
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.282
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     431
_refine_ls_number_reflns         4089
_refine_ls_number_restraints     198
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0607P)^2^+1.6582P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1254
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3425
_reflns_number_total             4089
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00441a2.cif
_cod_data_source_block           mo_d8v1718_0ma_3
_cod_depositor_comments
'Adding full bibliography for 7155507--7155508.cif.'
_cod_database_code               7155508
_olex2_refinement_description
;
1. Restrained distances
 F8A-C22 \\sim F9A-C22 \\sim F9-C22 \\sim F7-C22 \\sim F7A-C22 \\sim F8-C22
 with sigma of 0.02
 F9-C22 \\sim C22-F7A
 with sigma of 0.04
 F7A-C22 \\sim C22-F8A
 with sigma of 0.04
 F8A-C22 \\sim C22-F9
 with sigma of 0.04
 F7-C22 \\sim C22-F8
 with sigma of 0.04
 F8-C22 \\sim C22-F9A
 with sigma of 0.04
 F9A-C22 \\sim C22-F7
 with sigma of 0.04
 C10-C22 \\sim C22-F8
 with sigma of 0.04
 C10-C22 \\sim C22-F8A
 with sigma of 0.04
 C10-C22 \\sim C22-F9A
 with sigma of 0.04
 C10-C22 \\sim C22-F9
 with sigma of 0.04
 C10-C22 \\sim C22-F7
 with sigma of 0.04
 C10-C22 \\sim C22-F7A
 with sigma of 0.04
 F11A-C19 \\sim F10A-C19 \\sim F11-C19 \\sim F10-C19 \\sim F12A-C19 \\sim
F12-C19
 with sigma of 0.02
 F11A-C19 \\sim C19-F12A
 with sigma of 0.04
 F12A-C19 \\sim C19-F10A
 with sigma of 0.04
 F10A-C19 \\sim C19-F11A
 with sigma of 0.04
 F11-C19 \\sim C19-F12
 with sigma of 0.04
 F12-C19 \\sim C19-F10
 with sigma of 0.04
 F10-C19 \\sim C19-F10A
 with sigma of 0.04
 C15-C19 \\sim C19-F12
 with sigma of 0.04
 C15-C19 \\sim C19-F11A
 with sigma of 0.04
 C15-C19 \\sim C19-F11
 with sigma of 0.04
 C15-C19 \\sim C19-F10A
 with sigma of 0.04
 C15-C19 \\sim C19-F10
 with sigma of 0.04
 C15-C19 \\sim C19-F12A
 with sigma of 0.04
2. Uiso/Uaniso restraints and constraints
Uanis(F11) \\sim Ueq, Uanis(F11A) \\sim Ueq, Uanis(F12) \\sim Ueq, Uanis(F12A)
\\sim Ueq, Uanis(F10) \\sim Ueq, Uanis(F10A) \\sim Ueq: with sigma of 0.1 and
sigma for terminal atoms of 0.2
Uanis(F7) \\sim Ueq, Uanis(F7A) \\sim Ueq, Uanis(F8) \\sim Ueq, Uanis(F8A)
\\sim Ueq, Uanis(F9A) \\sim Ueq, Uanis(F9) \\sim Ueq: with sigma of 0.1 and
sigma for terminal atoms of 0.2
3. Rigid body (RIGU) restrains
 C22, F9A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C22, F9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C22, F7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C22, F7A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C22, F8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C22, F8A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F11A, F12, F12A, F10, F10A, F11, C19
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Others
 Sof(F9)=Sof(F7A)=Sof(F8A)=1-FVAR(1)
 Sof(F7)=Sof(F8)=Sof(F9A)=FVAR(1)
 Sof(F10)=Sof(F12)=Sof(F11)=1-FVAR(2)
 Sof(F10A)=Sof(F12A)=Sof(F11A)=FVAR(2)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'