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_4127719
_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
'C32 H22 N2 O3, 0.37(C H2 Cl2), 0.97(C2 H3 N)'
_chemical_formula_sum            'C34.31 H25.65 Cl0.74 N2.97 O3'
_chemical_formula_weight         553.58
_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             2019-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                104.496(4)
_cell_angle_beta                 94.554(5)
_cell_angle_gamma                97.803(5)
_cell_formula_units_Z            2
_cell_length_a                   6.9786(6)
_cell_length_b                   13.7874(11)
_cell_length_c                   14.7980(12)
_cell_measurement_reflns_used    9615
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.142
_cell_measurement_theta_min      2.864
_cell_volume                     1356.1(2)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0858
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            48014
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.369
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.4912
_exptl_absorpt_correction_T_min  0.4501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1670 before and 0.0617 after correction.
The Ratio of minimum to maximum transmission is 0.9163.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       needle
_exptl_crystal_F_000             578
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0192(18)
_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   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         5495
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0372P)^2^+0.9280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1166
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4233
_reflns_number_total             5495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b06363_si_002.cif
_cod_data_source_block           lpf29_2
_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               4127719
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.920
_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. Restrained distances
 Cl1-C1S = Cl2-C1S
 1.75 with sigma of 0.02
 N3S-C6S
 1.13 with sigma of 0.005
 C6S-C7S
 1.44 with sigma of 0.005
 N3S-C7S
 2.567 with sigma of 0.01
 Cl1-Cl2
 2.9 with sigma of 0.04
3. Others
 Sof(Cl1)=Sof(Cl2)=Sof(C1S)=Sof(H1SA)=Sof(H1SB)=FVAR(1)
 Sof(N1S)=Sof(C2S)=Sof(C3S)=Sof(H3SA)=Sof(H3SB)=Sof(H3SC)=FVAR(2)
 Sof(N2S)=Sof(C4S)=Sof(C5S)=Sof(H5SA)=Sof(H5SB)=Sof(H5SC)=FVAR(3)
 Sof(N3S)=Sof(C6S)=Sof(C7S)=Sof(H7SA)=Sof(H7SB)=Sof(H7SC)=FVAR(4)
 Fixed Uiso: N3S(0.075) C6S(0.075) C7S(0.075)
4.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6)
4.b Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB)
4.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C18(H18), C20(H20),
 C21(H21), C22(H22), C23(H23), C25(H25), C29(H29), C30(H30), C31(H31)
4.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C3S(H3SA,H3SB,H3SC), C5S(H5SA,H5SB,H5SC), C7S(H7SA,H7SB,
 H7SC)
;
_shelx_res_checksum              53125
_shelx_hkl_checksum              44549
_olex2_submission_special_instructions 'No special instructions were received'