#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:35:42 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257131 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/88/4038821.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_4038821
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         'C18 H15 N O'
_chemical_formula_sum            'C18 H15 N O'
_chemical_formula_weight         261.31
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 91.688(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4054(14)
_cell_length_b                   14.334(2)
_cell_length_c                   9.7907(15)
_cell_measurement_reflns_used    1426
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      22.78
_cell_measurement_theta_min      2.69
_cell_volume                     1319.4(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0880
_diffrn_reflns_av_sigmaI/netI    0.0613
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14415
_diffrn_reflns_theta_full        26.20
_diffrn_reflns_theta_max         26.20
_diffrn_reflns_theta_min         2.17
_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    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0398P)²+0.1611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                1687
_reflns_number_total             2646
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo0c01697_si_001.cif
_cod_data_source_block           Struct-8
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' 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_original_sg_symbol_H-M      'P 21/c  '
_cod_database_code               4038821
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.95650(14) 0.76315(10) 0.04831(13) 0.0292(4) Uani 1 1 d . . .
N1 N 0.89323(17) 0.73073(12) 0.26383(17) 0.0215(4) Uani 1 1 d . . .
H1 H 0.9199(19) 0.7337(13) 0.349(2) 0.016(5) Uiso 1 1 d . . .
C1 C 0.76606(19) 0.68121(14) 0.22980(18) 0.0211(4) Uani 1 1 d . . .
C2 C 0.7630(2) 0.58893(14) 0.26447(19) 0.0254(5) Uani 1 1 d . . .
H2A H 0.8427 0.5622 0.3117 0.030 Uiso 1 1 calc R . .
C3 C 0.6446(2) 0.53287(15) 0.2318(2) 0.0293(5) Uani 1 1 d . . .
H3A H 0.6416 0.4698 0.2616 0.035 Uiso 1 1 calc R . .
C4 C 0.5341(2) 0.56978(15) 0.1570(2) 0.0283(5) Uani 1 1 d . . .
H4A H 0.4556 0.5313 0.1312 0.034 Uiso 1 1 calc R . .
C5 C 0.53429(19) 0.66433(14) 0.11712(19) 0.0244(5) Uani 1 1 d . . .
C6 C 0.4246(2) 0.69846(16) 0.0295(2) 0.0296(5) Uani 1 1 d . . .
H6A H 0.3504 0.6578 -0.0009 0.036 Uiso 1 1 calc R . .
C7 C 0.4239(2) 0.78886(16) -0.0121(2) 0.0320(5) Uani 1 1 d . . .
H7A H 0.3546 0.8101 -0.0774 0.038 Uiso 1 1 calc R . .
C8 C 0.5261(2) 0.85035(15) 0.0424(2) 0.0271(5) Uani 1 1 d . . .
H8A H 0.5209 0.9143 0.0171 0.033 Uiso 1 1 calc R . .
C9 C 0.63396(19) 0.82229(14) 0.13096(19) 0.0228(4) Uani 1 1 d . . .
C10 C 0.64718(19) 0.72464(14) 0.16190(18) 0.0215(4) Uani 1 1 d . . .
C11 C 0.9790(2) 0.76956(14) 0.17260(19) 0.0220(4) Uani 1 1 d . . .
C12 C 1.1035(2) 0.82185(15) 0.2317(2) 0.0307(5) Uani 1 1 d . . .
H12A H 1.1904 0.8012 0.1879 0.046 Uiso 1 1 calc R . .
H12B H 1.1119 0.8099 0.3302 0.046 Uiso 1 1 calc R . .
H12C H 1.0899 0.8888 0.2159 0.046 Uiso 1 1 calc R . .
C13 C 0.72160(19) 0.89657(14) 0.19799(19) 0.0221(4) Uani 1 1 d . . .
C14 C 0.74808(19) 0.89645(14) 0.33892(19) 0.0236(5) Uani 1 1 d . . .
H14A H 0.7138 0.8464 0.3923 0.028 Uiso 1 1 calc R . .
C15 C 0.82317(19) 0.96776(14) 0.4020(2) 0.0261(5) Uani 1 1 d . . .
H15A H 0.8408 0.9661 0.4981 0.031 Uiso 1 1 calc R . .
C16 C 0.8729(2) 1.04162(14) 0.3265(2) 0.0270(5) Uani 1 1 d . . .
H16A H 0.9249 1.0906 0.3702 0.032 Uiso 1 1 calc R . .
C17 C 0.8464(2) 1.04373(14) 0.1869(2) 0.0278(5) Uani 1 1 d . . .
H17A H 0.8795 1.0946 0.1344 0.033 Uiso 1 1 calc R . .
C18 C 0.7720(2) 0.97198(14) 0.1236(2) 0.0261(5) Uani 1 1 d . . .
H18A H 0.7547 0.9740 0.0276 0.031 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
C11 N1 C1 124.68(16) . . ?
C11 N1 H1 117.3(12) . . ?
C1 N1 H1 117.9(12) . . ?
C2 C1 N1 116.67(17) . . ?
C2 C1 C10 121.09(18) . . ?
N1 C1 C10 122.25(18) . . ?
C1 C2 C3 121.35(19) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 H2A 119.3 . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C3 C4 C5 121.03(19) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C6 C5 C4 119.68(18) . . ?
C6 C5 C10 120.06(19) . . ?
C4 C5 C10 120.24(18) . . ?
C7 C6 C5 120.69(19) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C6 C7 C8 119.33(19) . . ?
C6 C7 H7A 120.3 . . ?
C8 C7 H7A 120.3 . . ?
C9 C8 C7 122.8(2) . . ?
C9 C8 H8A 118.6 . . ?
C7 C8 H8A 118.6 . . ?
C8 C9 C10 118.40(18) . . ?
C8 C9 C13 117.25(18) . . ?
C10 C9 C13 124.12(17) . . ?
C1 C10 C5 116.38(18) . . ?
C1 C10 C9 125.81(17) . . ?
C5 C10 C9 117.78(17) . . ?
O1 C11 N1 122.50(18) . . ?
O1 C11 C12 122.02(18) . . ?
N1 C11 C12 115.47(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 117.64(18) . . ?
C18 C13 C9 121.15(17) . . ?
C14 C13 C9 121.07(18) . . ?
C15 C14 C13 121.12(19) . . ?
C15 C14 H14A 119.4 . . ?
C13 C14 H14A 119.4 . . ?
C14 C15 C16 120.38(18) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C15 C16 C17 119.47(19) . . ?
C15 C16 H16A 120.3 . . ?
C17 C16 H16A 120.3 . . ?
C18 C17 C16 120.09(19) . . ?
C18 C17 H17A 120.0 . . ?
C16 C17 H17A 120.0 . . ?
C17 C18 C13 121.28(18) . . ?
C17 C18 H18A 119.4 . . ?
C13 C18 H18A 119.4 . . ?
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 C11 1.232(2) . ?
N1 C11 1.342(2) . ?
N1 C1 1.422(2) . ?
N1 H1 0.867(19) . ?
C1 C2 1.366(3) . ?
C1 C10 1.427(3) . ?
C2 C3 1.403(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.361(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.410(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.410(3) . ?
C5 C10 1.428(3) . ?
C6 C7 1.358(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.399(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.375(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.437(3) . ?
C9 C13 1.487(3) . ?
C11 C12 1.493(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.394(3) . ?
C13 C14 1.395(3) . ?
C14 C15 1.378(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.381(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.383(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.381(3) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
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
C11 N1 C1 C2 116.6(2) . . . . ?
C11 N1 C1 C10 -62.9(3) . . . . ?
N1 C1 C2 C3 -177.95(17) . . . . ?
C10 C1 C2 C3 1.6(3) . . . . ?
C1 C2 C3 C4 4.0(3) . . . . ?
C2 C3 C4 C5 -2.8(3) . . . . ?
C3 C4 C5 C6 174.32(18) . . . . ?
C3 C4 C5 C10 -3.8(3) . . . . ?
C4 C5 C6 C7 -178.90(19) . . . . ?
C10 C5 C6 C7 -0.8(3) . . . . ?
C5 C6 C7 C8 -5.6(3) . . . . ?
C6 C7 C8 C9 4.0(3) . . . . ?
C7 C8 C9 C10 4.0(3) . . . . ?
C7 C8 C9 C13 -170.69(18) . . . . ?
C2 C1 C10 C5 -7.8(3) . . . . ?
N1 C1 C10 C5 171.66(16) . . . . ?
C2 C1 C10 C9 174.47(17) . . . . ?
N1 C1 C10 C9 -6.0(3) . . . . ?
C6 C5 C10 C1 -169.22(17) . . . . ?
C4 C5 C10 C1 8.9(3) . . . . ?
C6 C5 C10 C9 8.7(3) . . . . ?
C4 C5 C10 C9 -173.22(17) . . . . ?
C8 C9 C10 C1 167.52(18) . . . . ?
C13 C9 C10 C1 -18.1(3) . . . . ?
C8 C9 C10 C5 -10.1(3) . . . . ?
C13 C9 C10 C5 164.21(17) . . . . ?
C1 N1 C11 O1 -2.2(3) . . . . ?
C1 N1 C11 C12 177.38(18) . . . . ?
C8 C9 C13 C18 -45.1(3) . . . . ?
C10 C9 C13 C18 140.51(19) . . . . ?
C8 C9 C13 C14 130.52(19) . . . . ?
C10 C9 C13 C14 -43.9(3) . . . . ?
C18 C13 C14 C15 -0.9(3) . . . . ?
C9 C13 C14 C15 -176.67(17) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C16 C17 C18 -0.6(3) . . . . ?
C16 C17 C18 C13 0.3(3) . . . . ?
C14 C13 C18 C17 0.5(3) . . . . ?
C9 C13 C18 C17 176.25(17) . . . . ?
