Modeling Biologically Important NH···π Interactions Using <i>peri</i>-Disubstituted Naphthalenes.
Pozharskii, Alexander F.; Dyablo, Olga V.; Pogosova, Olga G.; Ozeryanskii, Valery A.; Filarowski, Aleksander; Vasilikhina, Kseniya M.; Dzhangiryan, Narek A.; The Journal of organic chemistry 85 (2020) 12468–12481; doi:10.1021/acs.joc.0c01697

data_4038822
_publ_section_title
;
 Modeling Biologically Important NH&#x00B7;&#x00B7;&#x00B7;\p Interactions
 Using <i>peri</i>-Disubstituted Naphthalenes.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12468
_journal_page_last               12481
_journal_paper_doi               10.1021/acs.joc.0c01697
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         '2(B F4), C26 H18 N2, H2 O'
_chemical_formula_sum            'C26 H20 B2 F8 N2 O'
_chemical_formula_weight         550.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-11-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.152(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3987(4)
_cell_length_b                   13.0464(4)
_cell_length_c                   12.6405(4)
_cell_measurement_reflns_used    5243
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.7700
_cell_measurement_theta_min      4.5910
_cell_volume                     2344.30(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -103.00 -64.00   0.50    2.00    --  -38.95 -43.00 162.00   78
  2  \w    -23.00  27.00   0.50    2.00    --   38.95 -43.00 162.00  100
  3  \w     35.00  60.00   0.50    2.00    --   38.95  43.00 -45.00   50
  4  \w     72.00 101.00   0.50    2.00    --   38.95  43.00 -45.00   58
  5  \w     92.00 125.00   0.50   15.80    --  100.00  43.00 -45.00   66
  6  \w     34.00  99.00   0.50   15.80    --  100.00 -43.00 162.00  130
  7  \w    -53.00  33.00   0.50    2.00    --  -38.95  21.00 120.00  172
  8  \w    -59.00 -17.00   0.50    2.00    --  -38.95 -65.00 150.00   84
  9  \w   -104.00 -64.00   0.50    2.00    --  -38.95 -65.00 150.00   80
 10  \w     -3.00  23.00   0.50    2.00    --  -38.95  43.00  90.00   52
 11  \w    -54.00 -14.00   0.50    2.00    --  -38.95  43.00  90.00   80
 12  \w    -48.00 -23.00   0.50    2.00    --  -38.95 -43.00 162.00   50
 13  \w    -50.00  24.00   0.50    2.00    --  -38.95  43.00 -45.00  148
 14  \w    -56.00   6.00   0.50    2.00    --  -38.95  54.00 150.00  124
 15  \w     -7.00  19.00   0.50    2.00    --   38.95 -32.00   0.00   52
 16  \w     19.00  45.00   0.50    2.00    --   38.95  65.00  90.00   52
 17  \w     52.00  86.00   0.50    2.00    --   38.95  65.00  90.00   68
 18  \w     11.00  37.00   0.50    2.00    --   38.95-138.00 -60.00   52
 19  \w     51.00 116.00   0.50   15.80    --  100.00 -53.00-120.00  130
 20  \w     68.00 111.00   0.50   15.80    --  100.00-111.00 120.00   86
 21  \w    100.00 129.00   0.50   15.80    --  100.00 -86.00-120.00   58
 22  \w     31.00  65.00   0.50   15.80    --  100.00 -30.00 120.00   68
 23  \w     35.00  67.00   0.50   15.80    --  100.00 -69.00  60.00   64
 24  \w     33.00  89.00   0.50   15.80    --  100.00 -37.00 -60.00  112
 25  \w     55.00  97.00   0.50   15.80    --  100.00-111.00-120.00   84
 26  \w     85.00 132.00   0.50   15.80    --  100.00  37.00 -60.00   94
 27  \w     78.00 122.00   0.50   15.80    --  100.00-133.00  60.00   88
 28  \w     70.00 156.00   0.50   15.80    --  100.00  15.00  30.00  172
 29  \w     30.00 117.00   0.50   15.80    --  100.00 -22.00 -30.00  174
 30  \w     33.00  61.00   0.50   15.80    --  100.00 -37.00  30.00   56
 31  \w     47.00  72.00   0.50   15.80    --  100.00-133.00  60.00   50
 32  \w     50.00  76.00   0.50   15.80    --  100.00 -86.00-120.00   52
 33  \w    127.00 156.00   0.50   15.80    --  100.00 133.00-180.00   58
 34  \w     47.00  73.00   0.50   15.80    --  100.00 -69.00  90.00   52
 35  \w     83.00 133.00   0.50   15.80    --  100.00  93.00 -60.00  100
 36  \w     95.00 120.00   0.50   15.80    --  100.00  45.00-180.00   50
 37  \w     86.00 112.00   0.50   15.80    --  100.00  22.00 -60.00   52
 38  \w     66.00 128.50   0.50   15.80    --  100.00   7.00 -90.00  125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0259475000
_diffrn_orient_matrix_UB_12      -0.0331367000
_diffrn_orient_matrix_UB_13      -0.1085613000
_diffrn_orient_matrix_UB_21      0.0884400000
_diffrn_orient_matrix_UB_22      -0.0543700000
_diffrn_orient_matrix_UB_23      0.0585386000
_diffrn_orient_matrix_UB_31      -0.0569622000
_diffrn_orient_matrix_UB_32      -0.0995002000
_diffrn_orient_matrix_UB_33      0.0042547000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12516
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.524
_diffrn_reflns_theta_min         3.109
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.50a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         4459
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0598
_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^)+(0.0950P)^2^+0.9552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1696
_refine_ls_wR_factor_ref         0.1797
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3547
_reflns_number_total             4459
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01697_si_001.cif
_cod_data_source_block           Struct-31
_cod_depositor_comments
'Adding full bibliography for 4038815--4038822.cif.'
_cod_original_cell_volume        2344.31(12)
_cod_database_code               4038822
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C36 H18 N2 B2 F8'
_diffrn_oxdiff_ac3_digest_frames
;
01ecbe054497064430e70b321bff36011802981e8ea
;
_diffrn_oxdiff_ac3_digest_hkl
;
018e408db1a8d65929be42e6abd22b6ef7f156
;
_reflns_odcompleteness_completeness 98.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=1-FVAR(1)
 Sof(F1)=Sof(F4)=Sof(F2)=Sof(F3)=FVAR(1)
3.a Free rotating group:
 O1S(H1SA,H1SB)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C12(H12), C25(H25), C23(H23), C24(H24), C11(H11), C19(H19),
 C14(H14), C20(H20), C10(H10), C16(H16), C15(H15), C1(H1A), C7(H7), C6(H6),
 C2(H2A), C3(H3)
;
_shelx_res_checksum              57819
_shelx_hkl_checksum              74690
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.495
_oxdiff_exptl_absorpt_empirical_full_min 0.619