Electrostatically Driven CO-π Aromatic Interactions.
Li, Ping; Vik, Erik C.; Maier, Josef M.; Karki, Ishwor; Strickland, Sharon M. S.; Umana, Jessica M.; Smith, Mark D.; Pellechia, Perry J.; Shimizu, Ken D.; Journal of the American Chemical Society 141 (2019) 12513–12517; doi:10.1021/jacs.9b06363

data_4127712
_publ_section_title
;
 Electrostatically Driven CO-\p Aromatic Interactions.
;
_journal_issue                   32
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12513
_journal_page_last               12517
_journal_paper_doi               10.1021/jacs.9b06363
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C24 H16 F2 N2 O3'
_chemical_formula_sum            'C24 H16 F2 N2 O3'
_chemical_formula_weight         418.39
_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             2019-05-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                76.7260(10)
_cell_angle_beta                 82.520(2)
_cell_angle_gamma                83.0070(10)
_cell_formula_units_Z            2
_cell_length_a                   6.9174(2)
_cell_length_b                   10.5842(3)
_cell_length_c                   13.1785(4)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.395
_cell_measurement_theta_min      2.806
_cell_volume                     926.87(5)
_computing_cell_refinement       'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22240
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.456
_diffrn_reflns_theta_min         2.262
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0794 before and 0.0501 after correction.
The Ratio of minimum to maximum transmission is 0.9328.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.058(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         3816
_refine_ls_number_restraints     63
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0215P)^2^+0.8399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3216
_reflns_number_total             3816
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b06363_si_002.cif
_cod_data_source_block           lpe261
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4127712
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.978
_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. Shared sites
{C7A, C7B}
{C8A, C8B}
{C9A, C9B}
{C10A, C10B}
{C11A, C11B}
{C12A, C12B}
3. Restrained distances
 C10B-F1B
 1.4 with sigma of 0.0075
 C1-C13A \\sim C1-C13B \\sim C6-C18A \\sim C6-C18B
 with sigma of 0.005
 C18B-C15B \\sim C13B-C16B \\sim C17B-C14B
 with sigma of 0.015
 C13B-C15B \\sim C14B-C16B \\sim C15B-C17B \\sim C16B-C18B \\sim C17B-C13B
\\sim C18B-C14B
 with sigma of 0.02
4. Restrained planarity
 F2A, C15A, C14A, C13A, C18A, C17A, C16A
 with sigma of 0.015
 F2B, C15B, C14B, C13B, C18B, C17B, C16B
 with sigma of 0.015
5. Uiso/Uaniso restraints and constraints
Uanis(C13A) = Uanis(C13B)
Uanis(C18A) = Uanis(C18B)
Uanis(C7A) = Uanis(C7B)
Uanis(C8A) = Uanis(C8B)
Uanis(C9A) = Uanis(C9B)
Uanis(C10A) = Uanis(C10B)
Uanis(C11A) = Uanis(C11B)
Uanis(C12A) = Uanis(C12B)
Uanis(C17A) = Uanis(C17B)
Uanis(C16B) = Uanis(C16A)
Uanis(C15B) = Uanis(C15A)
Uanis(C14B) = Uanis(C14A)
6. Same fragment restrains
{F1A, C7A, C8A, C9A, C10A, C11A, C12A} sigma for 1-2: 0.01, 1-3: 0.04
as
{F2A, C13A, C14A, C15A, C16A, C17A, C18A}
{F1B, C7B, C8B, C9B, C10B, C11B, C12B} sigma for 1-2: 0.01, 1-3: 0.04
as
{F2B, C13B, C14B, C15B, C16B, C17B, C18B}
7. Others
 Sof(H1B)=Sof(H6B)=Sof(F1B)=Sof(C7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(H9B)=
 Sof(C10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(F2B)=Sof(C13B)=Sof(C14B)=Sof(H14B)=
 Sof(C15B)=Sof(H15B)=Sof(C16B)=Sof(C17B)=Sof(H17B)=Sof(C18B)=1-FVAR(1)
 Sof(H1A)=Sof(H6A)=Sof(F1A)=Sof(C7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(C10A)=
 Sof(H10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(F2A)=Sof(C13A)=Sof(C14A)=Sof(H14A)=
 Sof(C15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=FVAR(1)
8.a Ternary CH refined with riding coordinates:
 C1(H1A), C1(H1B), C2(H2), C5(H5), C6(H6A), C6(H6B)
8.b Aromatic/amide H refined with riding coordinates:
 C8A(H8A), C10A(H10A), C11A(H11A), C8B(H8B), C9B(H9B), C11B(H11B), C14A(H14A),
 C16A(H16A), C17A(H17A), C14B(H14B), C15B(H15B), C17B(H17B), C21(H21), C22(H22),
  C23(H23)
8.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_shelx_res_checksum              1024
_shelx_hkl_checksum              26574
_olex2_submission_special_instructions 'No special instructions were received'