#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:35:42 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257131 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/88/4038820.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4038820
loop_
_publ_author_name
'Pozharskii, Alexander F.'
'Dyablo, Olga V.'
'Pogosova, Olga G.'
'Ozeryanskii, Valery A.'
'Filarowski, Aleksander'
'Vasilikhina, Kseniya M.'
'Dzhangiryan, Narek A.'
_publ_section_title
;
 Modeling Biologically Important NH···π Interactions
 Using peri-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         'C17 H15 N O'
_chemical_formula_sum            'C17 H15 N O'
_chemical_formula_weight         249.30
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.165(3)
_cell_length_b                   17.073(9)
_cell_length_c                   12.098(7)
_cell_measurement_reflns_used    739
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      20.10
_cell_measurement_theta_min      3.37
_cell_volume                     1273.4(12)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1372
_diffrn_reflns_av_sigmaI/netI    0.1144
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11089
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2501
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1217
_refine_ls_R_factor_gt           0.0607
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0439P)²+0.0681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1414
_reflns_number_gt                1470
_reflns_number_total             2501
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo0c01697_si_001.cif
_cod_data_source_block           Struct-7
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4038815--4038822.cif.
;
_cod_database_code               4038820
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0479(5) 0.84112(16) 0.4746(2) 0.0375(7) Uani 1 1 d . . .
N1 N 0.0425(7) 0.8004(2) 0.0276(3) 0.0375(9) Uani 1 1 d . . .
H1 H 0.200(7) 0.777(2) 0.012(3) 0.046(12) Uiso 1 1 d . . .
H2 H 0.053(10) 0.831(4) 0.083(6) 0.10(2) Uiso 1 1 d . . .
C1 C -0.0398(6) 0.8612(2) 0.3735(3) 0.0302(10) Uani 1 1 d . . .
C2 C 0.0433(7) 0.9180(2) 0.3062(3) 0.0327(10) Uani 1 1 d . . .
H2A H 0.1666 0.9477 0.3278 0.039 Uiso 1 1 calc R . .
C3 C -0.0582(7) 0.9311(2) 0.2055(3) 0.0352(11) Uani 1 1 d . . .
H3A H -0.0034 0.9710 0.1583 0.042 Uiso 1 1 calc R . .
C4 C -0.2356(6) 0.8884(2) 0.1713(3) 0.0280(10) Uani 1 1 d . . .
C5 C -0.3177(6) 0.8322(3) 0.2435(3) 0.0333(10) Uani 1 1 d . . .
H5A H -0.4423 0.8028 0.2232 0.040 Uiso 1 1 calc R . .
C6 C -0.2195(6) 0.8189(2) 0.3442(3) 0.0324(10) Uani 1 1 d . . .
H6A H -0.2765 0.7806 0.3932 0.039 Uiso 1 1 calc R . .
C7 C -0.3454(6) 0.9040(2) 0.0638(3) 0.0290(9) Uani 1 1 d . . .
C8 C -0.5344(6) 0.9449(2) 0.0691(4) 0.0372(10) Uani 1 1 d . . .
H8A H -0.5907 0.9586 0.1396 0.045 Uiso 1 1 calc R . .
C9 C -0.6493(7) 0.9674(3) -0.0255(4) 0.0444(12) Uani 1 1 d . . .
H9A H -0.7810 0.9960 -0.0192 0.053 Uiso 1 1 calc R . .
C10 C -0.5699(7) 0.9480(3) -0.1263(4) 0.0446(12) Uani 1 1 d . . .
H10A H -0.6461 0.9641 -0.1907 0.053 Uiso 1 1 calc R . .
C11 C -0.3795(7) 0.9050(2) -0.1380(3) 0.0351(10) Uani 1 1 d . . .
C12 C -0.3066(8) 0.8836(3) -0.2442(4) 0.0434(12) Uani 1 1 d . . .
H12A H -0.3872 0.8991 -0.3074 0.052 Uiso 1 1 calc R . .
C13 C -0.1237(8) 0.8412(3) -0.2570(4) 0.0474(13) Uani 1 1 d . . .
H13A H -0.0741 0.8285 -0.3292 0.057 Uiso 1 1 calc R . .
C14 C -0.0069(7) 0.8159(3) -0.1651(3) 0.0410(11) Uani 1 1 d . . .
H14A H 0.1198 0.7851 -0.1754 0.049 Uiso 1 1 calc R . .
C15 C -0.0723(7) 0.8349(2) -0.0589(3) 0.0322(10) Uani 1 1 d . . .
C16 C -0.2612(6) 0.8812(2) -0.0417(4) 0.0300(9) Uani 1 1 d . . .
C17 C 0.2438(7) 0.8798(3) 0.5053(4) 0.0444(12) Uani 1 1 d . . .
H17A H 0.2931 0.8600 0.5771 0.067 Uiso 1 1 calc R . .
H17B H 0.2175 0.9363 0.5107 0.067 Uiso 1 1 calc R . .
H17C H 0.3554 0.8698 0.4494 0.067 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C17 116.6(3) . . ?
C15 N1 H1 119(2) . . ?
C15 N1 H2 112(4) . . ?
H1 N1 H2 107(5) . . ?
C2 C1 C6 121.6(4) . . ?
C2 C1 O1 123.8(4) . . ?
C6 C1 O1 114.5(4) . . ?
C1 C2 C3 117.9(4) . . ?
C1 C2 H2A 121.1 . . ?
C3 C2 H2A 121.1 . . ?
C4 C3 C2 122.4(4) . . ?
C4 C3 H3A 118.8 . . ?
C2 C3 H3A 118.8 . . ?
C3 C4 C5 117.7(4) . . ?
C3 C4 C7 121.8(4) . . ?
C5 C4 C7 120.4(4) . . ?
C6 C5 C4 120.5(4) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C1 C6 C5 119.8(4) . . ?
C1 C6 H6A 120.1 . . ?
C5 C6 H6A 120.1 . . ?
C8 C7 C16 119.5(4) . . ?
C8 C7 C4 116.1(4) . . ?
C16 C7 C4 124.4(3) . . ?
C7 C8 C9 122.4(4) . . ?
C7 C8 H8A 118.8 . . ?
C9 C8 H8A 118.8 . . ?
C10 C9 C8 119.1(4) . . ?
C10 C9 H9A 120.5 . . ?
C8 C9 H9A 120.5 . . ?
C9 C10 C11 121.7(4) . . ?
C9 C10 H10A 119.2 . . ?
C11 C10 H10A 119.2 . . ?
C10 C11 C12 119.9(4) . . ?
C10 C11 C16 119.8(4) . . ?
C12 C11 C16 120.4(4) . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C12 C13 C14 120.4(4) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
C15 C14 C13 121.2(4) . . ?
C15 C14 H14A 119.4 . . ?
C13 C14 H14A 119.4 . . ?
C14 C15 N1 116.7(4) . . ?
C14 C15 C16 120.3(4) . . ?
N1 C15 C16 122.7(4) . . ?
C15 C16 C7 125.3(4) . . ?
C15 C16 C11 117.0(4) . . ?
C7 C16 C11 117.6(3) . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.380(4) . ?
O1 C17 1.426(5) . ?
N1 C15 1.394(5) . ?
N1 H1 1.07(4) . ?
N1 H2 0.85(7) . ?
C1 C2 1.366(5) . ?
C1 C6 1.369(5) . ?
C2 C3 1.389(6) . ?
C2 H2A 0.9500 . ?
C3 C4 1.378(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.392(6) . ?
C4 C7 1.491(6) . ?
C5 C6 1.380(5) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.360(5) . ?
C7 C16 1.431(6) . ?
C8 C9 1.401(6) . ?
C8 H8A 0.9500 . ?
C9 C10 1.355(6) . ?
C9 H9A 0.9500 . ?
C10 C11 1.392(6) . ?
C10 H10A 0.9500 . ?
C11 C12 1.410(6) . ?
C11 C16 1.433(6) . ?
C12 C13 1.349(7) . ?
C12 H12A 0.9500 . ?
C13 C14 1.394(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.385(6) . ?
C14 H14A 0.9500 . ?
C15 C16 1.424(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 O1 C1 C2 -3.8(5) . . . . ?
C17 O1 C1 C6 175.9(4) . . . . ?
C6 C1 C2 C3 -1.1(6) . . . . ?
O1 C1 C2 C3 178.6(4) . . . . ?
C1 C2 C3 C4 -0.9(6) . . . . ?
C2 C3 C4 C5 2.2(6) . . . . ?
C2 C3 C4 C7 178.9(4) . . . . ?
C3 C4 C5 C6 -1.7(6) . . . . ?
C7 C4 C5 C6 -178.4(4) . . . . ?
C2 C1 C6 C5 1.6(6) . . . . ?
O1 C1 C6 C5 -178.2(3) . . . . ?
C4 C5 C6 C1 -0.1(6) . . . . ?
C3 C4 C7 C8 -102.3(5) . . . . ?
C5 C4 C7 C8 74.2(5) . . . . ?
C3 C4 C7 C16 75.6(5) . . . . ?
C5 C4 C7 C16 -107.8(5) . . . . ?
C16 C7 C8 C9 -1.5(6) . . . . ?
C4 C7 C8 C9 176.5(4) . . . . ?
C7 C8 C9 C10 0.0(6) . . . . ?
C8 C9 C10 C11 1.2(7) . . . . ?
C9 C10 C11 C12 177.7(4) . . . . ?
C9 C10 C11 C16 -1.0(6) . . . . ?
C10 C11 C12 C13 -179.3(4) . . . . ?
C16 C11 C12 C13 -0.7(6) . . . . ?
C11 C12 C13 C14 1.9(7) . . . . ?
C12 C13 C14 C15 -1.5(7) . . . . ?
C13 C14 C15 N1 173.8(4) . . . . ?
C13 C14 C15 C16 -0.2(6) . . . . ?
C14 C15 C16 C7 179.5(4) . . . . ?
N1 C15 C16 C7 5.9(6) . . . . ?
C14 C15 C16 C11 1.4(5) . . . . ?
N1 C15 C16 C11 -172.2(4) . . . . ?
C8 C7 C16 C15 -176.3(4) . . . . ?
C4 C7 C16 C15 5.8(6) . . . . ?
C8 C7 C16 C11 1.7(5) . . . . ?
C4 C7 C16 C11 -176.2(4) . . . . ?
C10 C11 C16 C15 177.7(4) . . . . ?
C12 C11 C16 C15 -1.0(5) . . . . ?
C10 C11 C16 C7 -0.5(5) . . . . ?
C12 C11 C16 C7 -179.2(4) . . . . ?
